Substituted 5-hydroxy-2-heteroaryl-3-phenylpentanonitrile derivatives, processes for their preparation and their use as herbicides and/or plant growth regulators

15-06-2017 дата публикации
Номер:
US20170166549A1
Принадлежит: Bayer Cropscience Aktiengesellshaft
Контакты:
Номер заявки: 60-32-1532
Дата заявки: 30-06-2015

[0001]

Primarily, the present invention relates to compounds of the formula (I) defined below and to their use as herbicides, in particular for controlling broad-leaved weeds and/or weed grasses in crops of useful plants and/or as plant growth regulators for influencing the growth of crops of useful plants. The present invention also relates to herbicidal or plant growth-regulating compositions comprising one or more compounds of the formula (I). Moreover, the present invention relates to processes for preparing the compounds of the formula (I).

[0002]

In their application, crop protection agents known to date for the selective control of harmful plants in crops of useful plants or active ingredients for controlling unwanted vegetation sometimes have disadvantages, be it (a) that they have no or else insufficient herbicidal activity against particular harmful plants, (b) that the spectrum of harmful plants which can be controlled with an active ingredient is not wide enough, (c) that their selectivity in crops of useful plants is too low and/or (d) that they have a toxicologically unfavorable profile. Furthermore, some active ingredients which can be used as plant growth regulators for a number of useful plants cause unwanted reduced harvest yields in other useful plants or are not compatible with the crop plant, or only within a narrow application rate range. Some of the known active ingredients cannot be produced economically on an industrial scale owing to precursors and reagents which are difficult to obtain, or they have only insufficient chemical stabilities. In the case of other active ingredients, the activity is too highly dependent on environmental conditions, such as weather and soil conditions.

[0003]

Inter alia, documents EP-A-0 005 341 (corresponding to U.S. Pat. No. 4,224,052), EP-A-0 266 725, EP-A-0 270 830, WO 2011/098417 A1, WO 2011/003775 A2, WO 2011/003776 A2, WO 2011/073143 A1, WO 2011/042378 A1, WO 2012/126764 A1, WO 2012/126765 A1, WO 2013/010882 A2, WO 2013/092500 A1 and WO 2014/095879 A1 disclose herbicidal cyanobutanoic acid derivatives.

[0004]

EP-A-0 005 341 describes herbicidal esters and amides of 4-cyano-3,4-diphenylbutanoic acids which are optionally substituted at the phenyl radicals. According to EP-A-0 005 341, the threo isomers are generally suitable for the non-selective control of harmful plants, whereas the erythro/threo isomer mixtures are suitable for the selective control of harmful plants in some crops of useful plants. Moreover, EP-A-0 005 341 mentions that the 2 enantiomers belonging to the threo form have different activities, which was investigated in an exemplary manner on the different activities of the enantiomers of the enantiomer pair of 4-cyano-3,4-diphenylbutanoic acid unsubstituted in the phenyl radicals.

[0005]

EP-A-0 266 725 discloses some erythro/threo isomer mixtures which can be used selectively for controlling weeds in rice crops.

[0006]

EP-A-0 270 830 describes that threo isomers and erythro/threo isomer mixtures can be used as plant regulators, preventing the development of an infructescence in various harmful grasses.

[0007]

WO 2011/003775 A2 discloses specific esters of 4-cyano-3,4-diphenylbutanoic acids which can be used as effective herbicides, preferably in crops of useful plants.

[0008]

WO 2011/003776 A2, WO 2011/042378 A1, WO 2011/073143 A1, WO 2012/126764 A1 and WO 2012/126765 A1 disclose 4-cyano-3,4-diphenylbutanoic acids and esters which have specific substitutions at the phenyl radicals and can be used as effective herbicides, preferably also in crops of useful plants.

[0009]

WO 2013/010882 describes 2,3-diphenylvaleronitrile derivatives and their use as herbicides and plant growth regulators.

[0010]

WO 2013/092500 A1 describes substituted 4-cyano-3-phenyl-4-(pyridin-3-yl) butanoates, processes for their preparation and their use as herbicides and plant growth regulators.

[0011]

WO 2014/095879 A1 describes substituted 4-cyano-3-(pyridyl)-4-phenylbutanoates and their use as herbicides and plant growth regulators.

[0012]

The herbicidal activity of these known compounds, in particular at low application rates, and/or their compatibility with crop plants remain deserving of improvement.

[0013]

For the reasons stated, there is still a need for potent herbicides and/or plant growth regulators for the selective use in crop plants or the use on non-crop land, where these active ingredients preferably should have further advantageous properties in application, for example with respect to their compatibility with crop plants.

[0014]

It is the primary object of the present invention to provide compounds having herbicidal activity (herbicides) which are highly effective against economically important harmful plants even at relatively low application rates and can be used selectively in crop plants, preferably with good activity for harmful plants, and at the same time preferably have good compatibility with crop plants. Preferably, these herbicidal compounds should be particularly effective and efficient against a broad spectrum of weed grasses and preferably also have good activity against a large number of weeds.

[0015]

Surprisingly, it has now been found that this object is achieved by the compounds of the formula (I) defined below and their salts.

[0016]

The present invention therefore relates to the compounds of the formula (I) and/or their salts,

[0000]

[0000]

in which

  • Q represents a mono- or bicyclic heteroaromatic radical with in total 1 to 9 carbon ring atoms, where the heteroatom or heteroatoms in the heteroaromatic ring are selected from the group consisting of N, O, S, P, B, Si, and Se,
  • R1represents hydrogen or a hydrolyzable radical,
  • (R2)nrepresent n substituents R2, where R2(if n=1) or each of the substituents R2(if n is greater than 1) independently of one another represents halogen, cyano, nitro, (C1-C8)alkyl, (C1-C8)alkoxy, (C1-C8)alkylthio, (C1-C8)alkylsulfinyl, (C1-C8)alkylsulfonyl, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy, (C1-C6)haloalkylthio, (C1-C6)haloalkylsulfinyl, (C1-C6)haloalkylsulfonyl, (C2-C6)alkenyl, (C2-C6)alkynyl, tri[(C1-C4)alkyl]silyl or tri[(C1-C4)alkyl]silyl(C1-C4)alkyl, or in each case two R2directly adjacent on the heteroaromatic radical Q are together a group of the formula —Z1-A*1-Z2—, in which
    • A* represents an alkylene group having 1 to 4 carbon atoms which is optionally substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy,
    • Z1represents a direct bond, O or S and
    • Z2represents a direct bond, O or S,
    • where the group —Z1-A*-Z2— together with the atoms of the heteroaromatic radical Q bonded to this group Q form a 5- or 6-membered ring (i.e. a ring with 5 or 6 ring atoms), and
      (R3)mrepresents m substituents R3,
    • where R3(if m=1) or each of the substituents R3(if m is greater than 1) independently of one another represents halogen, cyano, nitro, (C1-C8)alkyl, (C1-C8)alkoxy, (C1-C8)alkylthio, (C1-C8)alkylsulfinyl, (C1-C8)alkylsulfonyl, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy, (C1-C6)haloalkylthio, (C1-C6)haloalkylsulfinyl, (C1-C6)haloalkylsulfonyl, (C2-C6)alkenyl, (C2-C6)alkynyl, tri[(C1-C4)alkyl]silyl, tri-[(C1-C4)alkyl]silyl-(C1-C4)alkyl or —NR*R**, where R* and R**, independently of one another and independently of any other radicals —NR*R** present, are in each case selected from the group consisting of H, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C4)alkoxy-(C1-C4)alkyl, (C1-C6)alkanoyl, [(C1-C4)haloalkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, [(C1-C4)haloalkoxy]carbonyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkyl(C1-C4)alkyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkenyl-(C1-C4)alkyl, phenyl and phenyl-(C1-C4)alkyl, where each of the specified radicals (C3-C6)cycloalkyl, (C3-C6)cycloalkyl-(C1-C4)alkyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkenyl-(C1-C4)alkyl, phenyl and phenyl-(C1-C4)alkyl is substituted in the cycle optionally by one or more identical or different radicals Rbb, where
  • Rbbin each case represents halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy or (C1-C4)haloalkoxy and, in the case of (C3-C6)cycloalkyl, (C3-C6)cycloalkyl-(C1-C4)alkyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkenyl-(C1-C4)alkyl, Rbbmay additionally represent oxo, or
    • NR*R** represents a 3- to 8-membered heterocycle which, in addition to this nitrogen atom, optionally contains one or two further ring heteroatoms selected from the group consisting of N, O and S and which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)-alkyl, (C1-C4)-haloalkyl and oxo,
    • or where in each case two groups R3directly adjacent on the ring together represent a group of the formula —Z3-A**-Z4—, in which
    • A** represents an alkylene group having 1 to 4 carbon atoms which is optionally substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy,
    • Z3represents a direct bond, O or S and
    • Z4represents a direct bond, O or S,
    • where the group —Z3-A**-Z4together with the carbon atoms, bonded to this group, of the phenyl ring form a 5- or 6-membered ring,
      n represents 0, or an integer in the range from 1 to 5, preferably 0, 1, 2 or 3, and
      m represents 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2 or 3.

[0032]

The compounds of the formula (I) according to the invention and/or their salts have excellent herbicidal activity against a broad spectrum of economically important mono- and dicotyledonous annual harmful plants. The compounds according to the invention also have good control over perennial harmful plants which are difficult to control and produce shoots from rhizomes, root stocks or other perennial organs.

[0033]

The compounds of the formula (I) according to the invention and/or their salts, for example compared to the compounds described in WO 2012/126765 A1, generally have more potent action at the same dosage, for example against weed grasses. Furthermore, the compounds according to the invention have a broader spectrum of activity against weeds, i.e. the compounds according to the invention and/or their salts can be used to control effectively a relatively large number of different weeds.

[0034]

The compounds of the formula (I) according to the invention and/or their salts have proven to be very effective in controlling harmful plants such as Alopecurus myosuroides, Avena fatua, Cyperus esculentus, Echinochloa crus-galli, Lolium multiflorum, Setaria viridis, Abutilon theophrasti, Amaranthus retroflexus, Polygonum convolvulus (=Fallopia convolvulus), Stellaria media, Viola tricolor, and Veronica persica, where the preferred and particularly preferred compounds according to the invention exhibited in the biological tests an 80% to 100% herbicidal action against one, several or all of the specified harmful plants, and in so doing simultaneously more acceptable and mostly very slight damage to the useful plant.

[0035]

In addition, the compounds of the formula (I) according to the invention and/or their salts show particularly good activity in the pre-emergence method, in particular against weed grasses. The pre-emergence activity of the compounds according to the invention is generally better than the pre-emergence activity of the compounds described in WO 2012/126765 A1.

[0036]

Furthermore, it has been found that the compounds of the formula (I) according to the invention and/or their salts show this better pre-emergence action particularly selectively in certain crops, in particular in oilseed rape, soya beans, cotton and cereals (and here in particular in maize, barley, wheat, rye, oats, triticale, millet varieties, rice).

[0037]

In general, the compounds of the formula (I) according to the invention also have a considerably broader activity spectrum.

[0038]

In the formula (I), the formula “(R2)n” means n radicals R2which are attached as substituents at the heteroaromatic radical Q, where the radicals R2in the case of n greater than 1 may be identical or different and have the meaning mentioned in each case in more detail. In the case n=0, the heteroaromatic radical Q is not substituted by substituents R2.

[0039]

In the formula (I), the formula “(R3)m” means m radicals R3which are attached as substituents at the phenyl ring in question, where the radicals R3in the case of n greater than 1 may be identical or different and have the meaning mentioned in each case in more detail. In the case n=0, the phenyl ring in question is not substituted by substituents R3, i.e. all ring carbon atoms of the phenyl ring in positions 2 to 6 are attached to a hydrogen atom.

[0040]

In the case of R1═H or in the case of suitable acidic substituents, the compounds of the formula (I) are able to form salts by reaction with bases where the acidic hydrogen is replaced by an agriculturally suitable cation.

[0041]

By addition of a suitable inorganic or organic acid onto a basic group, such as, for example, amino or alkylamino, the compounds of the formula (I) are able to form salts. Suitable acidic groups present, such as, for example, carboxylic acid groups, are able to form inner salts with groups which for their part can be protonated, such as amino groups.

[0042]

The compounds of the formula (I) may preferably be present in the form of agriculturally usable salts, where the type of salt is otherwise generally immaterial. In general, suitable salts are the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the herbicidal activity of the compounds of the formula (I).

[0043]

Suitable cations are in particular ions of the alkali metals, here preferably lithium, sodium or potassium, of the alkaline earth metals, here preferably calcium or magnesium, and of the transition metals, here preferably manganese, copper, zinc or iron. The cation used may also be ammonium (NH4+) or substituted ammonium, where one to four hydrogen atoms may be replaced here by (C1-C4)alkyl, hydroxy-(C1-C4)alkyl, (C1-C4)alkoxy-(C1-C4)alkyl, hydroxy(C1-C4)alkoxy-(C1-C4)alkyl, phenyl or benzyl, preferred ammonium ions are ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium. Also suitable are phosphonium ions, sulfonium ions, preferably tri-(C1-C4)alkylsulfonium, in particular trimethylsulfonium, or sulfoxonium ions, preferably tri(C1-C4)alkylsulfoxonium, in particular trimethylsulfoxonium.

[0044]

Anions of suitable acid addition salts are preferably chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of (C1-C4)alkanoic acids, here in turn preferably formate, acetate, propionate, butyrate or trifluoroacetate.

[0045]

In formula (I) and in all subsequent formulae, chemical radicals are referred to by names which are collective terms for the enumeration of individual group members or specifically refer to individual chemical radicals. Here, terms are used which are familiar to the person skilled in the art or have the meanings defined below.

[0046]

A hydrolyzable radical (see definition of R1) is a radical which can be hydrolyzed under the application conditions, for example a radical which can be hydrolyzed even in the spray liquor or in particular under the physiological conditions in plants, where a compound of the formula (I) where R1is not hydrogen is hydrolyzed to the corresponding compound of the formula (I) where R1═H (hydrogen). Expressly, the definition of the hydrolyzable radicals also includes the radicals where R1=hydrocarbon radical or heterocyclyl radical, the two last-mentioned radicals being unsubstituted or substituted, even if some of them are hydrolyzable comparatively slowly.

[0047]

A hydrocarbon radical is an aliphatic, cycloaliphatic or aromatic monocyclic or, in the case of an optionally substituted hydrocarbon radical, also a bicyclic or polycyclic organic radical based on the elements carbon and hydrogen, including, for example, the radicals alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, phenyl, naphthyl, indanyl, indenyl, etc. This applies correspondingly to hydrocarbon radicals in composite meanings, such as hydrocarbonoxy radicals or other hydrocarbon radicals attached via heteroatom groups.

[0048]

Unless defined in more detail, the hydrocarbon radicals preferably have 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, in particular 1 to 12 carbon atoms.

[0049]

The hydrocarbon radicals, also in the special radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio, and also the corresponding unsaturated and/or substituted radicals may in each case be straight-chain or branched in the carbon skeleton.

[0050]

The expression “(C1-C4)alkyl” is shorthand for alkyl having from 1 to 4 carbon atoms, i.e. encompasses the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl. General alkyl radicals having a larger specified range of carbon atoms, for example “(C1-C6)alkyl”, correspondingly also encompass straight-chain or branched alkyl radicals having a greater number of carbon atoms, i.e. in this example also the alkyl radicals having 5 and 6 carbon atoms.

[0051]

Unless stated specifically or differently, preference is given to the lower carbon skeletons, for example having from 1 to 6 carbon atoms, or having from 2 to 6 carbon atoms in the case of unsaturated groups, in the case of the hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, including in composite radicals. Alkyl radicals, including in the combined definitions such as alkoxy, haloalkyl, etc., are, for example, methyl, ethyl, n- or i-propyl, n-, t- or 2-butyl, pentyls, hexyls such as n-hexyl, hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl radicals are defined as the possible unsaturated radicals corresponding to the alkyl radicals; alkenyl is, for example, vinyl, allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, pentenyl, 2-methylpentenyl or hexenyl group, preferably allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl or 1-methylbut-2-en-1-yl.

[0052]

Alkenyl also includes in particular straight-chain or branched hydrocarbon radicals having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulated double bonds, for example allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl.

[0053]

Alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. Alkynyl also includes, in particular, straight-chain or branched hydrocarbon radicals having more than one triple bond or else having one or more triple bonds and one or more double bonds, for example 1,3-butatrienyl or 3-penten-1-yn-1-yl.

[0054]

A 3- to 9-membered carbocyclic ring is (C3-C9)cycloalkyl or (C5-C9)cycloalkenyl.

[0055]

(C3-C9)Cycloalkyl is a carbocyclic saturated ring system having preferably 3-9 carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl or cyclononyl. In the case of substituted cycloalkyl, cyclic systems with substituents are included, where the substituents may also be bonded by a double bond on the cycloalkyl radical, for example an alkylidene group such as methylidene.

[0056]

(C5-C9)Cycloalkenyl is a carbocyclic, nonaromatic, partially unsaturated ring system having 5-9 carbon atoms, for example 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1,4-cyclohexadienyl. In the case of substituted cycloalkenyl, the explanations for substituted cycloalkyl apply correspondingly.

[0057]

Alkylidene, for example also in the form of (C1-C10)alkylidene, is the radical of a straight-chain or branched alkane which is bonded via a double bond, the position of the bonding site not being fixed. In the case of a branched alkane, the only positions possible are, of course, those in which two hydrogen atoms can be replaced by the double bond; radicals are, for example, ═CH2, ═CH—CH3, ═C(CH3)—CH3, C(CH3)—C2H5or C(C2H5)—C2H5.

[0058]

“Halogen” preferably refers to the group consisting of fluorine, chlorine, bromine and iodine. Haloalkyl, -alkenyl and -alkynyl are alkyl, alkenyl and alkynyl, respectively, which are partially or fully substituted by identical or different halogen atoms, preferably from the group consisting of fluorine, chlorine and bromine, in particular from the group consisting of fluorine and chlorine, for example monohaloalkyl, perhaloalkyl, CF3, CHF2, CH2F, CF3CF2, CH2FCHCl, CCl3, CHCl2, CH2CH2C1; haloalkoxy is, for example, OCF3, OCHF2, OCH2F, CF3CF2O, OCH2CF3and OCH2CH2C1; this applies correspondingly to haloalkenyl and other halogen-substituted radicals.

[0059]

Aryl is a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl.

[0060]

Optionally substituted aryl also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, where the point of attachment is at the aromatic system.

[0061]

A heterocyclic radical (heterocyclyl) comprises at least one heterocyclic ring (=carbocyclic ring in which at least one carbon atom is replaced by a heteroatom, preferably by a heteroatom from the group consisting of N, O, S, P, B, Si, Se), which is saturated, unsaturated or heteroaromatic and may be unsubstituted or substituted, where the point of attachment is located at a ring atom. Unless defined otherwise it preferably contains one or more, in particular 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably from the group consisting of N, O, and S; it is preferably an aliphatic heterocyclyl radical having 3 to 7 ring atoms or a heteroaromatic radical having 5 or 6 ring atoms. The heterocyclic radical may, for example, be a heteroaromatic radical or ring (heteroaryl), such as, for example, a monocyclic, bicyclic or polycyclic aromatic system in which at least 1 ring contains one or more heteroatoms.

[0062]

If the heterocyclyl radical or the heterocyclic ring is optionally substituted, it may be fused to other carbocyclic or heterocyclic rings. Preference is given to benzo-fused heterocyclic or heteroaromatic rings.

[0063]

Optionally substituted heterocyclyl also includes polycyclic systems, such as, for example, 8-aza-bicyclo[3.2.1]octanyl or 1-aza-bicyclo[2.2.1]heptyl. Optionally substituted heterocyclyl also includes spirocyclic systems, such as, for example, 1-oxa-5-aza-spiro[2.3]hexyl.

[0064]

Preferably it is a radical of a heteroaromatic ring with a heteroatom from the group consisting of N, O, and S, for example the radical of a five- or six-membered ring such as pyridyl, pyrrolyl, thienyl or furyl; with further preference it is a radical of a corresponding heteroaromatic ring having 2, 3 or 4 heteroatoms, such as pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, tetrazinyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl or triazolyl or tetrazolyl.

[0065]

Here, preference is given to a radical of a heteroaromatic five- or six-membered ring having 1 to 4 heteroatoms, such as, for example, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, tetrazolyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, 1,2,4,5-tetrazinyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl.

[0066]

More preference is given here to heteroaromatic radicals of five-membered heterocycles having 3 nitrogen atoms such as 1,2,3-triazol-1-yl, 1,2,3-triazol-4-yl, 1,2,3-triazol-5-yl, 1,2,5-triazol-1-yl, 1,2,5-triazol-3-yl, 1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl; more preference is also given to heteroaromatic radicals of six-membered heterocycles having 3 nitrogen atoms such as 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl, 1,2,3-triazin-4-yl, 1,2,3-triazin-5-yl; more preference is also given to heteroaromatic radicals of five-membered heterocycles having two nitrogen atoms and one oxygen atom such as 1,2,4-oxadiazol-3-yl; 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,5-oxadiazol-3-yl; more preference is also given to heteroaromatic radicals of five-membered heterocycles having two nitrogen atoms and one sulfur atom such as 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,5-thiadiazol-3-yl; more preference is also given to heteroaromatic radicals of five-membered heterocycles having four nitrogen atoms such as 1,2,3,4-tetrazol-1-yl, 1,2,3,4-tetrazol-5-yl, 1,2,3,5-tetrazol-1-yl, 1,2,3,5-tetrazol-4-yl, 2H-1,2,3,4-tetrazol-5-yl, 1H-1,2,3,4-tetrazol-5-yl, more preference is also given to heteroaromatic radicals of six-membered heterocycles such as 1,2,4,5-tetrazin-3-yl; more preference is also given to heteroaromatic radicals of five-membered heterocycles having three nitrogen atoms and one oxygen or sulfur atom such as 1,2,3,4-oxatriazol-5-yl; 1,2,3,5-oxatriazol-4-yl; 1,2,3,4-thiatriazol-5-yl; 1,2,3,5-thiatriazol-4-yl; more preference is also given to heteroaromatic radicals of six-membered heterocycles such as, for example, 1,2,4,6-thiatriazin-1-yl; 1,2,4,6-thiatriazin-3-yl; 1,2,4,6-thiatriazin-5-yl.

[0067]

Furthermore preferably, the heterocyclic radical or ring is a partially or fully hydrogenated heterocyclic radical having one heteroatom from the group of N, O and S, for example oxiranyl, oxetanyl, oxolanyl (=tetrahydrofuryl), oxanyl, pyrrolinyl, pyrrolidyl or piperidyl.

[0068]

It is also preferably a partially or fully hydrogenated heterocyclic radical having 2 heteroatoms from the group of N, O and S, for example piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl and morpholinyl. Suitable substituents for a substituted heterocyclic radical are the substituents specified later on below, and additionally also oxo. The oxo group may also occur on the ring heteroatoms which are able to exist in different oxidation states, as in the case of N and S, for example.

[0069]

Preferred examples of heterocyclyl are a heterocyclic radical having from 3 to 6 ring atoms from the group of pyridyl, thienyl, furyl, pyrrolyl, oxiranyl, 2-oxetanyl, 3-oxetanyl, oxolanyl (=tetrahydrofuryl), pyrrolidyl, piperidyl, especially oxiranyl, 2-oxetanyl, 3-oxetanyl or oxolanyl, or is a heterocyclic radical having two or three heteroatoms, for example pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl or morpholinyl.

[0070]

Preferred heterocyclic radicals are also benzo-fused heteroaromatic rings, for example benzofuryl, benzisofuryl, benzothiophenyl, benzisothiophenyl, isobenzothiophenyl, indolyl, isoindolyl, indazolyl, benzimidazolyl, benzotriazolyl, benzoxazolyl, 1,2-benzisoxazolyl, 2,1-benzisoxazolyl, benzothiazolyl, 1,2-benzisothiazolyl, 2,1-benzisothiazolyl, 1,2,3-benzoxadiazolyl, 2,1,3-benzoxadiazolyl, 1,2,3-benzothiadiazolyl, 2,1,3-benzothiadiazolyl, quinolyl (quinolinyl), isoquinolyl (isoquinolinyl), quinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzotriazinyl, purinyl, pteridinyl, indolizinyl, benzo-1,3-dioxylyl, 4H-benzo-1,3-dioxinyl and 4H-benzo-1,4-dioxinyl, and, where possible, N-oxides and salts thereof.

[0071]

When a base structure is substituted “by one or more radicals” from a list of radicals (=group) or a generically defined group of radicals, this in each case includes simultaneous substitution by a plurality of identical and/or structurally different radicals.

[0072]

Substituted radicals, such as a substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, phenyl, benzyl, heterocyclyl and heteroaryl radical, are, for example, a substituted radical derived from the unsubstituted base structure, where the substituents are, for example, one or more, preferably 1, 2 or 3, radicals from the group of halogen, alkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino such as acylamino, mono- and dialkylamino, and alkylsulfinyl, alkylsulfonyl and, in the case of cyclic radicals, also alkyl, haloalkyl, alkylthioalkyl, alkoxyalkyl, optionally substituted mono- and dialkylaminoalkyl and hydroxyalkyl; in the term “substituted radicals”, such as substituted alkyl, etc., substituents include, in addition to the saturated hydrocarbon-containing radicals mentioned, corresponding unsaturated aliphatic and aromatic radicals, such as optionally substituted alkenyl, alkynyl, alkenyloxy, alkynyloxy, phenyl and phenoxy, etc. In the case of substituted cyclic radicals having aliphatic moieties in the ring, cyclic systems with those substituents which are bonded on the ring by a double bond are also included, for example substituted by an alkylidene group such as methylidene or ethylidene.

[0073]

The term “radicals from the group consisting of” followed by a group (list of the substituents) is, wherever used, synonymous with “radicals selected from the group consisting of” (list of the substituents).

[0074]

The substituents mentioned by way of example (“first substituent level”) may, if they contain hydrocarbonaceous moieties, optionally be further substituted therein (“second substituent level”), for example by one of the substituents as defined for the first substituent level. Corresponding further substituent levels are possible. The term “substituted radical” preferably embraces just one or two substituent levels.

[0075]

Here, preferred substituents for the substituent levels are amino, hydroxyl, halogen, nitro, cyano, mercapto, carboxyl, carbonamide, SF5, aminosulfonyl, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, monoalkylamino, dialkylamino, N-alkanoylamino, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkenyloxy, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aryloxycarbonyl, alkanoyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, alkylthio, cycloalkylthio, alkenylthio, cycloalkenylthio, alkynylthio, alkylsulfinyl, alkylsulfonyl, monoalkylaminosulfonyl, dialkylaminosulfonyl, N-alkylaminocarbonyl, N,N-dialkylaminocarbonyl, N-alkanoylaminocarbonyl, N-alkanoyl-N-alkylaminocarbonyl, aryl, aryloxy, benzyl, benzyloxy, benzylthio, arylthio, arylamino and benzylamino.

[0076]

Two substituents together may also form a saturated or unsaturated hydrocarbon bridge or a corresponding bridge in which carbon atoms, CH groups or CH2groups are replaced by heteroatoms, thus forming a fused-on or fused cycle. Here, with preference benzo-fused systems based on the base structure are formed.

[0077]

Optionally substituted phenyl is preferably unsubstituted phenyl or phenyl which is substituted by one or more radicals from the group consisting of halogen, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy-(C1-C4)alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, alkylthio and nitro, in particular phenyl which is optionally substituted by one or more radicals from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl and (C1-C4)-alkoxy.

[0078]

In the case of substituents having carbon atoms, preference is given to those having 1 to 6 carbon atoms, preferably to those having 1 to 4 carbon atoms, especially to those having 1 or 2 carbon atoms. Preference is generally given to substituents from the group of halogen, for example fluorine and chlorine, (C1-C4)alkyl, preferably methyl or ethyl, (C1-C4)haloalkyl, preferably trifluoromethyl, (C1-C4)alkoxy, preferably methoxy or ethoxy, (C1-C4)haloalkoxy, nitro and cyano. Particular preference is given here to the substituents methyl, methoxy, fluorine and chlorine.

[0079]

Substituted amino, such as mono- or disubstituted amino, is a radical from the group of the substituted amino radicals which are N-substituted, for example, by one or two identical or different radicals from the group of alkyl, alkoxy, acyl and aryl; preferably mono- and dialkylamino, mono- and diarylamino, acylamino, N-alkyl-N-arylamino, N-alkyl-N-acylamino and N-heterocycles; preference is given to alkyl radicals having from 1 to 4 carbon atoms; aryl is preferably phenyl or substituted phenyl; acyl is as defined below, preferably (C1-C4)alkanoyl. The same applies to substituted hydroxylamino or hydrazino.

[0080]

Acyl is a radical of an organic acid which arises in a formal sense by removal of a hydroxyl group on the acid function, and the organic radical in the acid may also be bonded to the acid function via a heteroatom. Examples of acyl are the radicals of a carboxylic acid and radicals of acids derived therefrom, such as those of thiocarboxylic acid, optionally N-substituted iminocarboxylic acids or the radical of carbonic monoesters, N-substituted carbamic acid, sulfonic acids, sulfinic acids, N-substituted sulfonamide acids, phosphonic acids or phosphinic acids.

[0081]

Acyl is, for example, formyl, alkylcarbonyl, here preferably [(C1-C4)-alkyl]carbonyl, phenylcarbonyl, alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl and other radicals of organic acids. The radicals may each for their part be substituted in the alkyl or phenyl moiety, for example in the alkyl moiety by one or more radicals from the group of halogen, alkoxy, phenyl and phenoxy; examples of substituents in the phenyl moiety are the substituents already mentioned above in general for substituted phenyl.

[0082]

Acyl is preferably an acyl radical in the narrower sense, i.e. a radical of an organic acid in which the acid group is bonded directly to the carbon atom of an organic radical, for example formyl, alkylcarbonyl such as acetyl or [(C1-C4alkyl]carbonyl, phenylcarbonyl, alkylsulfonyl, alkylsulfinyl and other radicals of organic acids.

[0083]

In a preferred embodiment, acyl is an alkanoyl radical having 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms, particularly preferably 1 to 4 carbon atoms. Here, (C1-C4)alkanoyl is the radical of an alkanoic acid having 1 to 6 carbon atoms formed after removal of the OH group of the acid group, i.e. formyl, acetyl, n-propionyl, isopropionyl, n-, iso-, sec- or tert-butanoyl, n-, iso-, sec- or tert-pentanoyl, n-, iso- or sec-hexanoyl.

[0084]

The “yl position” of a radical denotes the carbon atom having the free bond.

[0085]

In the context of the present text, compounds of the formula (I) according to the invention and/or salts thereof are in short also referred to as “compounds (I)”.

[0086]

The invention also provides all stereoisomers which are encompassed by formula (I) and mixtures thereof. Compounds of the formula (I) contain two or more asymmetric carbon atoms, and may also contain double bonds, the stereochemistry of which is not stated separately in the general formula (I). The possible stereoisomers defined by their specific three-dimensional shape, such as enantiomers, diastereomers, Z- and E-isomers, are all encompassed by the formula (I) and can be obtained from mixtures of the stereoisomers by customary methods or else prepared by stereoselective reactions in combination with the use of stereochemically pure starting materials.

[0087]

The compounds of the formula (I) according to the invention include all stereoisomers which can occur on the basis of the centers of asymmetry or double bonds in the molecule whose configuration is not designated specifically in the respective structural formula or which are not specified explicitly, and mixtures thereof, including the racemic mixtures and the mixtures enriched partly with particular stereoisomers.

[0088]

The invention also provides all tautomers of the compounds of the formula (I) which may result from a hydrogen atom shift (for example keto-enol tautomers). The compound of the formula (I) also includes the tautomers, even if formally the formula (I) correctly describes only one of the respective tautomers which are in equilibrium with one another or which can be converted into one another.

[0089]

The compounds of the formula (I) also include all physical forms in which they may be present as a pure substance or, if appropriate, as a mixture with other substances, in particular also polymorphic crystal forms of the compounds of the formula (I) and salts thereof and solvent adducts (for example hydrates).

[0090]

Primarily for reasons of higher herbicidal activity, better selectivity and/or better producibility, compounds of the abovementioned formula (I) according to the invention or their salts or their use according to the invention are of particular interest in which individual radicals have one of the preferred meanings already specified or specified below, or in particular those in which one or more of the preferred meanings already specified or specified below occur in combination.

[0091]

Irrespective of the respective other radicals from the group consisting of R1, (R2)nand (R3)mand the subdefinitions corresponding to the general radicals, and preferably in combination with preferred definitions of one or more of these radicals, compounds according to the invention with the preferred meanings listed below of the radicals in question are of particular interest.

[0092]

According to the invention, preference is given to compounds of the formula (I) and/or their salts, characterized in that

  • Q represents a mono- or bicyclic heteroaromatic radical having in total 2 to 9 carbon ring atoms, where the heteroaromatic radical Q contains 1, 2, 3 or 4 heteroatoms in the heteroaromatic ring and the heteroatom or the heteroatoms are selected from the group consisting of N, O, and S.

[0094]

According to the invention, preference is given to compounds of the formula (I) and/or their salts, characterized in that

[0095]

According to the invention, further preference is given to compounds of the formula (I) and/or their salts, characterized in that

  • Q represents a mono- or bicyclic heteroaromatic radical selected from the group consisting of pyrimidinyl, pyridinyl, pyridazinyl, pyrazinyl, thienyl, furyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, triazinyl, quinolyl, isoquinolyl, cinnolinyl-, quinazolinyl, quinoxalinyl, pteridinyl, indolyl and phthalazinyl.

[0097]

Preferably, Q is a mono- or bicyclic heteroaromatic radical having in total 3 to 9 carbon ring atoms, where at least one of the heteroatoms present in the heteroaromatic ring is N or S, where further preferably at least one of the heteroatoms present in the heteroaromatic ring is N.

[0098]

Here, in turn preferably Q is a heteroaromatic 5- or 6-membered ring (i.e. a heteroaromatic ring with 5 or 6 ring atoms), in which preferably all heteroatoms present in the heteroaromatic ring are N.

[0099]

According to the invention, particular preference is given to compounds of the formula (I) and/or their salts, in which Q is pyridyl, corresponding to the formulae (I-1), (I-2) and (I-3) defined below:

[0000]

[0000]

where
R1, R2, R3, m and n in each case have the meaning defined above or below.

[0100]

Particularly preferred compounds of the formula (I) according to the invention correspond to the above-defined formula (I-2), i.e. a meaning of Q particularly preferred according to the invention is 3-pyridyl.

[0101]

Preference is given to compounds of the formula (I) according to the invention or salts thereof in which

  • R1represents hydrogen or a hydrolyzable radical having a total of up to 30 carbon atoms, preferably a hydrolyzable radical having a total of 1 to 24 carbon atoms, preferably having a total of 1 to 20 carbon atoms, more preferably having a total of 1 to 16 carbon atoms, particularly preferably having a total of 1 to 12 carbon atoms.

[0103]

Further preference is given to compounds of the formula (I) or salts thereof in which

[0000]

R1represents hydrogen or a hydrolyzable radical having in total 1 to 24 carbon atoms, where R1

    • represents an optionally substituted hydrocarbon radical or an optionally substituted heterocyclyl radical, or
    • represents a radical of the formula SiRaRbRc, or —NRaRb, where each of the radicals Raand Rbindependently of the other represents hydrogen or an optionally substituted hydrocarbon radical and Rcindependently represents an optionally substituted hydrocarbon radical, or —NRaRbrepresents a 3- to 9-membered heterocycle which, in addition to this nitrogen atom, may contain one or two further ring heteroatoms from the group consisting of N, O and S and which is substituted or unsubstituted, or
    • represents a radical of the formula —C(═O)—Reor —P(═O)(Rf)2, where W and both radicals Rfin each case independently of one another are selected from the group consisting of hydrogen, OH, unsubstituted or substituted (C1-C8)alkyl, unsubstituted or substituted (C1-C4)haloalkyl, unsubstituted or substituted (C2-C8)alkenyl, unsubstituted or substituted (C2-C8)alkynyl, unsubstituted or substituted (C1-C6)alkoxy, unsubstituted or substituted (C1-C6)alkoxy-(C1-C8)alkyl, unsubstituted or substituted (C1-C4)haloalkoxy, unsubstituted or substituted (C1-C4)haloalkoxy-(C1-C8)alkyl, unsubstituted or substituted (C3-C8)alkenyloxy, unsubstituted or substituted (C3-C8)alkenyloxy-(C1-C8)alkyl, unsubstituted or substituted (C3-C8)alkynyloxy, unsubstituted or substituted (C3-C8)alkynyloxy-(C1-C8)alkyl, unsubstituted or substituted —NR*R**, where R* and R** are as defined above, unsubstituted or substituted tri-[(C1-C4)alkyl]silyl, unsubstituted or substituted tri-[(C1-C4)alkyl]silyl-(C1-C8)alkyl, unsubstituted or substituted (C3-C6)cycloalkyl, unsubstituted or substituted (C3-C6)cycloalkyl-(C1-C8)alkyl, unsubstituted or substituted (C5-C6)cycloalkenyl, unsubstituted or substituted (C5-C6)cycloalkenyl-(C1-C8)alkyl, unsubstituted or substituted (C5-C6)cycloalkynyl, unsubstituted or substituted (C5-C6)cycloalkynyl-(C1-C8)alkyl, unsubstituted or substituted phenyl, unsubstituted or substituted phenyl-(C1-C8)alkyl, unsubstituted or substituted phenoxy, unsubstituted or substituted phenoxy-(C1-C8)alkyl, unsubstituted or substituted phenylamino, unsubstituted or substituted phenylamino(C1-C8)alkyl, unsubstituted or substituted Het, unsubstituted or substituted Het-(C1-C6)alkyl and unsubstituted or substituted Het-O—(C1-C6)alkyl, where
  • Het in each case represents a saturated, partially unsaturated or heteroaromatic monocyclic heterocyclyl radical having 3 to 9 ring atoms or a 9- or 10-membered bicyclic heterocycle in each case containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where each of the specified substituted radicals is substituted in the acyclic moiety by one or more identical or different radicals RAand/or where each of the specified substituted radicals is substituted in the cyclic moiety by one or more identical or different radicals RB, where
    RArepresents halogen, cyano, hydroxy or (C1-C6)alkoxy, and
  • RBindependently of any further radicals RBpresent is selected from the group consisting of halogen, cyano, hydroxy, oxo, nitro, (C1-C8)alkyl, (C1-C6)haloalkyl, cyano-(C1-C6)alkyl, hydroxy-(C1-C6)alkyl, nitro-(C1-C6)alkyl, (C2-C8)alkenyl, (C2-C8)haloalkenyl, (C2-C8)alkynyl, (C2-C8)haloalkynyl, (C1-C8)alkoxy, (C2-C8)alkenyloxy, (C2-C8)alkynyloxy, (C1-C8)haloalkoxy, (C1-C6)alkoxy-(C1-C6)alkyl, (C1-C6)alkoxy, —(C1-C4)alkoxy, (C1-C6)haloalkoxy-(C1-C4)alkyl, (C1-C6)haloalkoxy-(C1-C4)alkoxy, (C1-C8)alkylthio, (C2-C6)alkenylthio, (C2-C6)alkynylthio, (C1-C8)alkylsulfinyl, (C1-C6)haloalkylsulfinyl, (C1-C8)alkylsulfonyl, (C1-C6)haloalkylsulfonyl, Raa—C(═O)—, Raa—C(═O)—(C1-C6)alkyl, —NR*R**, tri-[(C1-C4)alkyl]silyl, tri-[(C1-C4)alkyl]silyl-(C1-C6)alkyl, (C3-C8)cycloalkyl, (C3-C8)cycloalkoxy, (C3-C8)cycloalkyl-(C1-C8)alkyl, (C3-C8)cycloalkyl-(C1-C8)alkoxy, phenyl, phenyl-(C1-C8)alkyl, phenoxy, phenoxy-(C1-C8)alkyl, phenylamino, phenylamino-(C1-C8)alkyl or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where each of these specified radicals can be substituted in the cyclic moiety by one or more identical or different Rbb, where
  • Raain each case independently of one another represent hydrogen, OH, (C1-C8)alkyl, (C1-C6)haloalkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)alkoxy, (C1-C6)alkoxy-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkyloxy, (C1-C6)haloalkoxy, (C1-C6)haloalkoxy-(C1-C6)alkyl, (C1-C6)haloalkoxy-(C1-C6)alkoxy, (C3-C8)alkenyloxy, (C3-C8)alkenyloxy-(C1-C6)alkyl, (C3-C8)alkenyloxy-(C1-C6)alkoxy, (C3-C8)alkynyloxy, (C3-C8)alkynyloxy-(C1-C6)alkyl, (C3-C8)alkynyloxy, —(C1-C6)alkoxy, —NR*R**, tri-[(C1-C4)alkyl]silyl, tri-[(C1-C4)alkyl]silyl-(C1-C6)alkyl, tri-[(C1-C4)alkyl]silyl-(C1-C6)alkoxy, (C3-C8)cycloalkyl, (C3-C8)cycloalkoxy, (C3-C8)cycloalkyl-(C1-C8)alkyl, (C3-C8)cycloalkyl-(C1-C8)alkoxy, (C5-C8)cycloalkenyl, (C5-C8)cycloalkenyl-(C1-C6)alkyl, (C5-C8)cycloalkenyloxy, (C5-C8)cycloalkynyl, (C5-C8)cycloalkynyl-(C1-C6)alkyl, (C5-C8)cycloalkynyl-(C1-C6)alkoxy, phenyl, phenyl-(C1-C8)alkyl, phenyl-(C1-C8)alkoxy, phenoxy, phenoxy-(C1-C8)alkyl, phenoxy-(C1-C8)alkoxy, phenylamino, phenylamino-(C1-C8)alkyl, phenylamino-(C1-C8)alkoxy or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle containing 1, 2, 3 or 4 heteroatoms and optionally bonded via an alkylene group or an alkoxy group is selected from the group consisting of O, N and S, where each of the radicals Raaencompassing a cycle is optionally substituted in the cyclic moiety by one or more identical or different radicals Rbb, and
    where R*, R**, —NR*R** and Rbbhave the meaning given above.

[0110]

Further preference is given to compounds of the formula (I) or salts thereof in which

  • R1represents hydrogen, unsubstituted (C1-C18)alkyl, unsubstituted (C2-C18)alkenyl, unsubstituted (C2-C18)alkynyl, substituted (C1-C18)alkyl, substituted (C2-C18)alkenyl or substituted (C2-C18)alkynyl, where in the case of substituted (C1-C18)alkyl, substituted (C2-C18)alkenyl and substituted (C2-C18)alkynyl the substituent(s) is/are each independently of one another selected from groups (a)-(e) below:
    • (a) halogen, cyano, thio, nitro, hydroxy, carboxy, (C1-C8)alkoxy, (C2-C8)alkenyloxy, (C2-C8)alkynyloxy, (C1-C8)haloalkoxy, (C1-C4)alkoxy, —(C1-C4)alkoxy, (C1-C8)alkylthio, (C2-C8)alkenylthio, (C2-C8)alkyinylthio, (C1-C8)haloalkylthio, (C2-C8)haloalkenylthio, (C2-C8)haloalkinylthio, (C1-C8)alkylsulfinyl, (C2-C8)alkenylsulfinyl, (C2-C8)alkynylsulfinyl, (C1-C8)haloalkylsulfinyl, (C2-C8)haloalkenylsulfinyl, (C2-C8)haloalkinylsulfinyl, (C1-C8)alkylsulfonyl, (C2-C8)alkenylsulfonyl, (C2-C8)alkynylsulfonyl, (C1-C8)haloalkylsulfonyl, (C2-C8)haloalkenylsulfonyl, (C2-C8)haloalkynylsulfonyl, —NR*R**,
      • where R*, R** and —NR*R** each have the meaning given above,
    • (b) (C3-C8)cycloalkyl, (C5-C8)cycloalkenyl, (C5-C8)cycloalkinyl, (C3-C8)cycloalkyl-(C1-C6)alkoxy, (C3-C8)cycloalkyl-(C1-C6)alkyl-S(O)p—, (C5-C8)cycloalkenyl-(C1-C6)alkoxy, (C5-C8)cycloalkenyl-(C1-C6)alkyl-S(O)p—, (C5-C8)cycloalkynyl-(C1-C6)alkoxy, (C5-C8)cycloalkynyl-(C1-C6)alkyl-S(O)p—, (C3-C8)cycloalkoxy, (C3-C8)cycloalkyl-S(O)p—, (C5-C8)cycloalkenyloxy, (C5-C8)cycloalkenyl-S(O)p—, (C5-C8)cycloalkynyloxy, (C5-C8)cycloalkynyl-S(O)p—, (C3-C8)cycloalkoxy, —(C1-C6)alkoxy, (C3-C8)cycloalkoxy-(C1-C6)alkyl-S(O)p—, phenyl, phenyl(C1-C6)alkoxy, phenoxy, phenyl-S(O)p—, phenyl-(C1-C6)alkyl-S(O)p—, phenoxy-(C1-C6)alkoxy, phenoxy-(C1-C6)alkyl-S(O)p—, a radical Het1, Het1-S(O)—, Het1-(C1-C6)alkoxy, Het1-O—, Het1-O—(C1-C6)alkoxy, where the radical Het1has the meaning given above, and where each of the last-mentioned radicals of the group (b) in the acyclic moiety is unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, hydroxy and (C1-C6)alkoxy, and/or in the cyclic moiety is unsubstituted or substituted by one or more identical or different radicals RB, where RBhas the meaning given above, and the index p is in each case 0, 1 or 2,
    • (c) —C(═O)—RC, —C(═O)—O—RC, —O—C(═O)—RC, —O—C(═O)—O—RC, —C(═O)—S—RC, —C(═S)—S—RC, —C(═S)—S—RC, —C(═O)—NR*R**, —C(═O)—O—NR*R**, —O—C(═O)—NR*R**, —N(R*)—C(═O)—RC, —N(R*)—C(═O)—NR*R**, —N(R*)—C(═O)—O—RC, —P(═O)(RC)(RD), —P(═O)(ORC)(RD), —P(═O)(ORC)(ORD) or —O—P(═O)(ORC)(ORD), where R*, R** and —NR*R** each have the meaning given above and RCand RDare as defined below,
    • (d) —SiR′3, —O—SiR′3, (R′)3Si—(C1-C6)alkoxy, —CO—O—NR′2, —O—N═CR′2, —N═CR′2, —O—NR′2, —CH(OR′)2and —O—(CH2)q—CH(OR′)2, in which each of the radicals R′ is independently selected from the group consisting of H, (C1-C4)alkyl or phenyl which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)haloalkyl, (C1-C4)haloalkoxy and nitro or substituted at two adjacent positions by a (C2-C6)alkylene bridge, and the index q is an integer from 0 to 6, and
    • (e) R″O—CHR′″CH(OR″)—(C1-C6)alkoxy,
      • in which each of the radicals R″ independently of the others represents H or (C1-C4)alkyl or together the radicals represent a (C1-C6)alkylene group and R′″ represents H or (C1-C4)alkyl,
    • or
      R1(C3-C9)cycloalkyl, (C5-C9)cycloalkenyl, (C5-C9)cycloalkynyl or phenyl,
    • where each of these radicals is unsubstituted or substituted by one or more radicals from the group consisting of the radicals of subgroups (a′)-(e′) below:
    • (a′) halogen, cyano, thio, nitro, hydroxy, carboxy, (C1-C8)alkyl, (C1-C8)haloalkyl, (C1-C4)alkoxy-(C1-C4)alkyl, (C2-C8)alkenyl, (C2-C8)haloalkenyl, (C2-C8)alkynyl, (C2-C8)haloalkynyl, (C1-C8)alkoxy, (C2-C8)alkenyloxy, (C2-C8)alkynyloxy, (C1-C8)haloalkoxy, (C1-C4)alkoxy-(C1-C4)alkoxy, (C1-C8)alkylthio, (C2-C8)alkenylthio, (C2-C8)alkynylthio and —NR*R**, where R*, R**, —NR*R**, and Rbbin each case have the meaning given above,
    • (b′) radicals of the formulae —C(═O)—RC, —C(═O)—O—RC, —O—C(═O)—RC, —O—C(═O)—O—RC, —C(═O)—S—RC, —C(═S)—S—RC, —C(═O)—NR*R**, —C(═O)—O—NR*R**, —O—C(═O)—NR*R**, —N(R*)—C(═O)—RC, —N(R*)—C(═O)—NR*R**, —N(R*)—C(═O)—O—RC, —P(═O)(RC)(RD), —P(═O)(ORC)(RD), —P(═O)(ORC)(ORD) or —O—P(═O)(ORC)(ORD),
      • where R*, R**, —NR*R** and Rbbhave the meaning given above and RCand RDhave the meaning defined below,
    • (c′) radicals of the formulae —SiR′3, —O—SiR′3, (R′)3Si—(C1-C6)alkoxy, —CO—O—NR12, —O—N═CR′2, —N═CR′2, —O—NR′2, —CH(OR′)2and —O—(CH2)q—CH(OR′)2,
      • in which each of the radicals R1independently of the others represents H, (C1-C4)-alkyl or phenyl which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)haloalkyl, (C1-C4)haloalkoxy and nitro or is substituted at two adjacent positions by a (C2-C6)alkylene bridge, and q represents an integer from 0 to 6, and
    • (d′) radicals of the formula R″O—CHR′″CH(OR″)—(C1-C6)alkoxy,
      • in which each of the radicals R″ independently of the others represents H or (C1-C4)alkyl or together the radicals represent a (C1-C6)alkylene group and R′″ represents H or (C1-C4)alkyl, and
    • (e′) a radical of the formula Het1which is unsubstituted or substituted by one or more identical or different radicals RB, where RBhas the meaning given above,
    • or
  • R1represents a polycyclic radical based on (C3-C9)cycloalkyl, (C5-C9)cycloalkenyl, (C5-C9)cycloalkynyl or phenyl, where the base ring is fused with a carbocyclic or heterocyclic ring, preferably a 5- or 6-membered ring having 0, 1, 2 or 3 ring heteroatoms from the group consisting of N, O and S, preferably benzo-fused, and where the base ring or the polycyclic system is unsubstituted or substituted by one or more identical or different radicals RB, where RBhas the meaning given above,
    • is preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, hydroxy, carboxy, (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C4)alkoxy-(C1-C4)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, (C2-C6)alkynyl, (C2-C6)haloalkynyl, (C1-C6)alkoxy, (C2-C6)alkenyloxy, (C2-C6)alkynyloxy, (C1-C6)haloalkoxy, (C1-C4)alkoxy-(C1-C4)alkoxy, (C1-C6)alkylthio, (C2-C6)alkenylthio, (C2-C6)alkynylthio, (C3-C6)cycloalkyl, (C3-C6)cycloalkoxy, [(C1-C8)alkoxy]carbonyl, [(C1-C6)haloalkoxy]carbonyl and oxo,
    • or
  • R1is a heterocyclic radical Het1, which is unsubstituted in the ring or in the polycyclic system or is substituted by one or more identical or different radicals RB, where RBhas the meaning given above, preferably is unsubstituted or substituted by one or more radicals from the group halogen, cyano, thio, nitro, hydroxy, carboxy, (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C4)alkoxy-(C1-C4)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, (C2-C6)alkynyl, (C2-C6)haloalkynyl, (C1-C6)alkoxy, (C2-C6)alkenyloxy, (C2-C6)alkynyloxy, (C1-C6)haloalkoxy, (C1-C4)alkoxy-(C1-C4)alkoxy, (C1-C6)alkylthio, (C2-C6)alkenylthio, (C2-C6)alkynylthio, (C3-C6)cycloalkyl, (C3-C6)cycloalkoxy, [(C1-C8)alkoxy]carbonyl, [(C1-C6)haloalkoxy]carbonyl and oxo,
    where
  • Het1in each case independently of the others is a saturated, partially unsaturated or heteroaromatic monocyclic heterocyclyl radical having 3 to 9 ring atoms, preferably having 5 or 6 ring atoms, or a 9- or 10-membered bicyclic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, preferably a 5- or 6-membered heterocycle having 1 to 3 ring heteroatoms from the group consisting of N, O and S which is optionally also fused to a carbocyclic or heterocyclic ring, preferably a carbocyclic ring having 3 to 6 carbon atoms or a heterocyclic ring having 5 or 6 ring atoms and 1 to 3 ring heteroatoms from the group consisting of N, O and S, preferably optionally benzo-fused,
    RAhas the meaning given above,
  • RBhas the meaning given above, and where RBpreferably represents a radical selected from the group consisting of halogen, cyano, hydroxy, oxo, nitro, (C1-C6)alkyl, (C1-C4)haloalkyl, cyano-(C1-C4)alkyl, hydroxy-(C1-C4)alkyl, nitro-(C1-C4)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, (C2-C6)alkynyl, (C2-C6)haloalkynyl, (C1-C6)alkoxy, (C2-C6)alkenyloxy, (C2-C6)alkynyloxy, (C1-C6)haloalkoxy, (C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)alkoxy-(C1-C4)alkoxy, (C1-C4)haloalkoxy-(C1-C4)alkyl, (C1-C4)haloalkoxy, —(C1-C4)alkoxy, (C1-C6)alkylthio, (C2-C6)alkenylthio, (C2-C6)alkynylthio, (C1-C6)alkylsulfinyl, (C1-C6)haloalkylsulfinyl, (C1-C6)alkylsulfonyl, (C1-C6)haloalkylsulfonyl, a radical of the formulaaa—C(═O)— or Raa—C(═O)—(C1-C6)alkyl, where Raahas the meaning given above, —NR*R**, where R*, R**, —NR*R**, and Rbbin each case have the meaning given above, tri-[(C1-C4)alkyl]silyl, tri-[(C1-C4)alkyl]silyl-(C1-C6)alkyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkoxy, (C3-C6)cycloalkyl-(C1-C4)alkyl, (C3-C6)cycloalkyl-(C1-C8)alkoxy, phenyl, phenyl-(C1-C6)alkyl, phenoxy, phenoxy-(C1-C6)alkyl, phenylamino, phenylamino-(C1-C6)alkyl, or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where each of the radicals RBin the cyclic moiety is optionally substituted by one or more identical or different radicals Rbb, where RBand Rbbin each case have the meaning given above,
  • RCand RDeach independently of one another (and also independently of radicals RC, RDin other groups) represent a radical selected from the group consisting of:
    • (i) hydrogen, unsubstituted (C1-C8)alkyl, unsubstituted (C2-C8)alkenyl, unsubstituted (C2-C8)alkynyl, substituted (C1-C8)alkyl, substituted (C2-C8)alkenyl, and substituted (C2-C8)alkynyl, where each of these substituted radicals is substituted by one or more radicals from the group halogen, cyano, nitro, hydroxy, (C1-C6)alkoxy, (C2-C6)alkenyloxy, (C2-C6)alkynyloxy, (C1-C8)haloalkoxy, (C1-C4)alkoxy-(C1-C4)alkoxy, (C1-C8)alkylthio, (C1-C8)haloalkylthio, (C1-C8)alkylsulfinyl, (C1-C8)haloalkylsulfinyl, (C1-C8)alkylsulfonyl, (C1-C8)haloalkylsulfonyl and tri-[(C1-C4)alkyl]silyl,
    • and
    • (ii) (C3-C8)cycloalkyl, (C5-C8)cycloalkenyl, (C5-C8)cycloalkynyl, phenyl, (C3-C8)cycloalkyl-(C1-C6)alkyl, (C5-C8)cycloalkenyl-(C1-C6)alkyl, (C5-C8)cycloalkynyl-(C1-C6)alkyl, phenyl-(C1-C6)alkyl, (C3-C8)cycloalkyloxy-(C1-C6)alkyl, (C3-C8)cycloalkyl-S(O)p—(C1-C6)alkyl, (C5-C8)cycloalkenyloxy-(C1-C6)alkyl, (C5-C8)cycloalkynyloxy-(C1-C6)alkyl, phenoxy-(C1-C6)alkyl, phenyl-S(O)p—(C1-C6)alkyl, (C3-C8)cycloalkylamino-(C1-C6)alkyl, (C5-C8)cycloalkenylamino-(C1-C6)alkyl, (C5-C8)cycloalkynylamino-(C1-C6)alkyl, phenylamino-(C1-C6)alkyl, Het1, Het1-(C1-C6)alkyl, Het1-O—(C1-C6)alkyl or Het1-S(O)p(C1-C6)alkyl, where Het1has the meaning given above, and where each of these radicals is unsubstituted in the acyclic moiety or substituted by one or more identical or different radicals RAand in the cyclic moiety is unsubstituted or substituted by one or more identical or different radicals RBand p in each case represents 0, 1 or 2, where RAand RBin each case have the meaning given above,
  • Raahas the meaning given above, and where Raapreferably independently is a radical selected from the group consisting of hydrogen, OH, (C1-C6)alkyl, (C1-C4)haloalkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)alkoxy-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkyloxy, (C1-C4)haloalkoxy, (C1-C4)haloalkoxy-(C1-C6)alkyl, (C1-C4)haloalkoxy-(C1-C6)alkoxy, (C3-C6)alkenyloxy, (C3-C6)alkenyloxy-(C1-C6)alkyl, (C3-C6)alkenyloxy-(C1-C6)alkoxy, (C3-C6)alkynyloxy, (C3-C6)alkynyloxy-(C1-C6)alkyl, (C3-C6)alkynyloxy-(C1-C6)alkoxy, —NR*R**, where R* and R** are as defined above, tri[(C1-C4)alkyl]silyl, tri[(C1-C4)alkyl]silyl-(C1-C6)alkyl, tri[(C1-C4)alkyl]silyl-(C1-C6)alkoxy, (C3-C6)cycloalkyl, (C3-C6)cycloalkoxy, (C3-C6)cycloalkyl-(C1-C8)alkyl, (C3-C6)cycloalkyl-(C1-C8)alkoxy, (C5-C6)cycloalkenyl, (C5-C6)cycloalkenyl-(C1-C6)alkyl, (C5-C6)cycloalkenyloxy, (C5-C6)cycloalkynyl, (C5-C6)cycloalkynyl-(C1-C6)alkyl, (C5-C6)cycloalkynyl-(C1-C6)alkoxy, phenyl, phenyl-(C1-C6)alkyl, phenyl-(C1-C6)alkoxy, phenoxy, phenoxy-(C1-C6)alkyl, phenoxy-(C1-C6)alkoxy, phenylthio, phenyl-S(O)p—(C1-C6)alkyl, phenyl-S(O)p—(C1-C6)alkoxy, where p in each case independently of one another is 0, 1 or 2, phenylamino, phenylamino-(C1-C6)alkyl, phenylamino-(C1-C6)alkoxy or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle optionally bonded via an alkylene group or an alkoxy group, containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where each of the specified cyclic radicals Raain the cyclic moiety is optionally substituted by one or more identical or different radicals selected from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy.

[0141]

For reasons of stronger herbicidal activity, better selectivity and better or easier handling, inter alia, compounds of the formula (I) according to the invention and/or salts thereof in which R1═H (hydrogen), preferably compounds of the formula (Ia) defined below, are particularly preferable in the context of the present invention.

[0142]

Particular preference is likewise given to compounds of the formula (I) according to the invention and/or salts thereof which, under application conditions, comparatively easily lead to a compound of the formula (I) where R1═H, for example by degradation or hydrolysis.

[0143]

In this case, the actual structure of group R1is not critical, where as mentioned preferably under the application conditions for example by (enzymatic) degradation, cleavage or hydrolysis at least to some extend a compound of the formula (I) where R1═H, preferably a compound of the formula (Ia) defined below, is formed.

[0144]

In the context of what was discussed above, in a preferred aspect R1represents hydrogen or a group selected from the group consisting of —C(═O)—RC, —C(═O)—O—RC, —C(═O)—S—RC, —C(═S)—S—RCand —C(═O)—NR*R**, particularly preferably hydrogen or a group —C(═O)—RC, where RC, R* and R** each have the meaning defined above, preferably each have one of the meanings given above as being preferred.

[0145]

Especially preferably, R1represents hydrogen or a group selected from the group consisting of —C(═O)—RCand —C(═O)—O—RC, here in turn particularly preferably hydrogen or —C(═O)—RC, where RCpreferably comprises a total of 1 to 16 carbon atoms, with preference a total of 1 to 12 carbon atoms.

[0146]

Particularly preferably, RCin each case particularly preferably represents a radical selected from the group consisting of:

[0000]

(i) hydrogen, unsubstituted (C1-C8)alkyl, unsubstituted (C2-C8)alkenyl, unsubstituted (C2-C8)alkynyl, substituted (C1-C8)alkyl, substituted (C2-C8)alkenyl, and substituted (C2-C8)alkynyl, where each of these substituted radicals is substituted by one or more radicals from the group halogen, cyano, hydroxy, (C1-C4)alkoxy, (C2-C6)alkenyloxy, (C1-C4)haloalkoxy, (C1-C4)alkoxy-(C1-C4)alkoxy, (C1-C6)alkylthio, (C1-C6)haloalkylthio, (C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl, (C1-C8)haloalkylsulfonyl and tri[(C1-C4)alkyl]silyl,
and
(ii) (C3-C8)cycloalkyl, (C5-C8)cycloalkenyl, phenyl, phenyl-(C1-C6)alkyl, (C3-C8)cycloalkyloxy-(C1-C6)alkyl, phenoxy-(C1-C6)alkyl, Het1, Het1-(C1-C6)alkyl, Het1-O—(C1-C6)alkyl, where Het1has the meaning mentioned above and where each of these radicals in the acyclic moiety is unsubstituted or substituted by one or more identical or different radicals RAand in the cyclic moiety is unsubstituted or substituted by one or more identical or different radicals RB, where RAand RBin each case have the meaning given above, where in turn preferably RAand RBhave the following meaning:

  • RAindependently of any other radicals RApresent is selected from the group consisting of halogen, cyano, hydroxy and (C1-C4)alkoxy, and
  • RBindependently of any other radicals RBpresent is selected from the group consisting of halogen, cyano, hydroxy, nitro, (C1-C6)alkyl, (C1-C6)haloalkyl, cyano-(C1-C6)alkyl, hydroxy-(C1-C6)alkyl, (C2-C8)alkenyl, (C2-C8)haloalkenyl, (C2-C6)alkynyl, (C2-C6)haloalkynyl, (C1-C6)alkoxy, (C2-C6)alkenyloxy, (C1-C6)haloalkoxy, (C1-C6)alkoxy-(C1-C4)alkyl, (C1-C4)alkoxy-(C1-C4)alkoxy, (C1-C4)haloalkoxy-(C1-C4)alkyl, (C1-C4)haloalkoxy-(C1-C4)alkoxy, (C1-C6)alkylthio, (C2-C6)alkenylthio, (C1-C6)alkylsulfinyl, (C1-C6)haloalkylsulfinyl, (C1-C6)alkylsulfonyl, and (C1-C6)haloalkylsulfonyl,
    where RCpreferably comprises a total of 1 to 16 carbon atoms, with preference a total of 1 to 12 carbon atoms.

[0149]

In formula (I), especially preferably R1represents hydrogen, —C(═O)—O—RCor —C(═O)—RC, where the group RCis in each case selected from the group consisting of:

[0000]

(i) unsubstituted (C1-C6)alkyl, unsubstituted (C2-C6)alkenyl, unsubstituted (C2-C6)alkynyl, substituted (C1-C6)alkyl, substituted (C2-C6)alkenyl and substituted (C2-C6)alkynyl, where each of these substituted radicals is substituted by one or more radicals from the group consisting of methyl, hydroxy, fluorine and chlorine,
(ii) (C3-C6)cycloalkyl, (C3-C6)cycloalkyloxy-(C1-C4)alkyl, phenyl, where each of these radicals in the cyclic moiety is unsubstituted or substituted by one or more identical or different radicals RB, where RBindependently of any other radicals RBpresent is selected from the group consisting of halogen (here preferably fluorine, chlorine, bromine), cyano, nitro and (C1-C4)alkyl (here in turn preferably methyl),
where RCpreferably comprises a total of 1 to 12 carbon atoms, with preference a total of 1 to 10 carbon atoms.

[0150]

In formula (I), R1especially preferably represents hydrogen or a group selected from the group consisting of:

[0000]

acetyl, propanoyl, butanoyl, pentanoyl, hexanoyl, 2-methylpropanoyl (=isopropanoyl), 2,2-difluoroacetyl, 2,2,2-trifluoroacetyl, C(═O)OMe, cyclopropanecarbonyl, 1-methylcyclopropanecarbonyl, acryl, prop-2-ynoyl, but-2-ynoyl, 2-methylacryl, benzoyl, 4-chlorobenzoyl, 3-chlorobenzoyl, 2-chlorobenzoyl, 4-fluorobenzoyl, 3-fluorobenzoyl, 2-fluorobenzoyl, 2,2-dimethylpropanoyl (=pivaloyl), 3,3-dimethylbutanoyl, 2-nitrobenzoyl, 2-fluoroacetyl, 2-chloroacetyl, 2-bromoacetyl, 2,2-dichloroacetyl, 2-methoxyacetyl, 2,6-difluorobenzoyl, C(O)C(═O)OMe and C(O)CH2C(O)OMe.

[0151]

In formula (I), R1especially preferably represents hydrogen or a group selected from the group consisting of:

[0000]

acetyl, propanoyl, butanoyl, pentanoyl, hexanoyl, 2-methylpropanoyl (=isopropanoyl), 2,2-difluoroacetyl, 2,2,2-trifluoroacetyl, C(═O)OMe, cyclopropanecarbonyl, 1-methylcyclopropanecarbonyl, acryl, prop-2-ynoyl, but-2-ynoyl, 2-methylacryl, benzoyl, 4-chlorobenzoyl, 3-chlorobenzoyl, 2-chlorobenzoyl, 4-fluorobenzoyl, 3-fluorobenzoyl, 2-fluorobenzoyl, 2,2-dimethylpropanoyl (=pivaloyl), 3,3-dimethylbutanoyl and 2-nitrobenzoyl.

[0152]

Further preference is given to compounds of the formula (I) according to the invention or salts thereof in which

[0000]

(R2)nrepresents n substituents R2,

    • where R2(if n=1) or each of the substituents R2(if n is greater than 1) independently of the others represents halogen, cyano, nitro, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)alkylthio, (C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy, (C1-C6)haloalkylthio, (C1-C6)haloalkylsulfinyl, (C1-C6)haloalkylsulfonyl, (C2-C6)alkenyl, (C2-C6)alkynyl, tri[(C1-C4)alkyl]silyl or tri[(C1-C4)alkyl]silyl-(C1-C4)alkyl,
    • and/or
      (R3)mrepresents m substituents R3,
    • where R3(if m=1) or each of the substituents R3(if m is greater than 1) independently of the others represents halogen, cyano, nitro, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)alkylthio, (C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy, (C1-C6)haloalkylthio, (C1-C6)haloalkylsulfinyl, (C1-C6)haloalkylsulfonyl, (C2-C6)alkenyl, (C2-C6)alkynyl, NR*R**, tri[(C1-C4)alkyl]silyl or tri[(C1-C4)alkyl]silyl(C1-C4)alkyl,
    • or where in each case two groups R3directly adjacent on the ring together represent a group of the formula —Z3-A**-Z4, in which
    • A** represents an alkylene group having 1 to 4 carbon atoms which is optionally substituted by one or more radicals from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy,
    • Z3represents a direct bond, O or S and
    • Z4represents a direct bond, O or S,
    • where the group —Z3-A**-Z4together with the carbon atoms, attached to the group, of the phenyl ring form a fused-on 5- or 6-membered ring,
  • R*, R** each independently of one another or together with the nitrogen atom have the meaning given above,
  • n, m in each case independently of one another are 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2 or 3, in particular 0, 1 or 2,
    where in addition preferably
    R1is hydrogen or a group selected from the group consisting of:
    acetyl, propanoyl, butanoyl, pentanoyl, hexanoyl, 2-methylpropanoyl (=isopropanoyl), 2,2-difluoroacetyl, 2,2,2-trifluoroacetyl, C(═O)OMe, cyclopropanecarbonyl, 1-methylcyclopropanecarbonyl, acryl, prop-2-ynoyl, but-2-ynoyl, 2-methylacryl, benzoyl, 4-chlorobenzoyl, 3-chlorobenzoyl, 2-chlorobenzoyl, 4-fluorobenzoyl, 3-fluorobenzoyl, 2-fluorobenzoyl, 2,2-dimethylpropanoyl (=pivaloyl), 3,3-dimethylbutanoyl, 2-nitrobenzoyl, 2-fluoroacetyl, 2-chloroacetyl, 2-bromoacetyl, 2,2-dichloroacetyl, 2-methoxyacetyl, 2,6-difluorobenzoyl, C(O)C(═O)OMe and C(O)CH2C(O)OMe.

[0163]

Further preference is given to compounds of the formula (I) according to the invention or salts thereof or of the formula (Ia) defined below or salts thereof, in which

[0000]

(R2)nrepresents n substituents R2,

    • where, in the case that n=1, the substituent R2or, in the case that n is greater than 1, each of the substituents R2independently of the others represents
    • halogen, cyano, nitro, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)alkylsulfinyl, (C1-C4)alkylsulfonyl, (C1-C4)haloalkyl, (C2-C4)haloalkenyl, (C1-C4)haloalkoxy, (C1-C4)haloalkylthio, (C1-C4)haloalkylsulfinyl, (C1-C4)haloalkylsulfonyl, (C2-C4)alkenyl, (C2-C4)alkynyl, tri[(C1-C4)alkyl]silyl or tri[(C1-C4)alkyl]silyl (C1-C4)alkyl and
      n represents 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, in particular 0, 1 or 2,
      and/or
      (R3)mrepresents m substituents R3,
    • where in the case that m=1, the substituent R3or, in the case that m is greater than 1, each of the substituents R3independently of one another represents halogen, cyano, nitro, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)alkylsulfinyl, (C1-C4)alkylsulfonyl, (C1-C4)haloalkyl, (C2-C4)haloalkenyl, (C1-C4)haloalkoxy, (C1-C4)haloalkylthio, (C1-C4)haloalkylsulfinyl, (C1-C4)haloalkylsulfonyl, (C2-C6)alkenyl, (C2-C6)alkynyl or tri-[(C1-C4)alkyl]silyl-Zb—, where Zb=is a covalent bond or (C1-C4)alkylene, or
    • in each case two groups R3directly adjacent to one another at the ring together represent a group of the formula —Z3-A**-Z4,
    • where
    • A** represents an alkylene group which is optionally substituted by one or more radicals from the group halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy,
    • Z3represents O or S and
    • Z4represents O or S, where the group —Z3-A**-Z4together with the carbon atoms, attached to the group, of the phenyl ring form a fused-on 5- or 6-membered ring,
      m represents 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2, 3 or 4, in particular 0, 1, 2 or 3.

[0172]

Further preference is given to compounds of the formula (I) according to the invention or salts thereof or of the formula (Ia) defined below or salts thereof, in which

[0000]

(R2)nrepresents n substituents R2,

    • where, in the case that n=1, the substituent R2or, in the case that n is greater than 1, each of the substituents R2independently of one another represents fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethyl, trifluoromethoxy, trifluoroalkylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, and
      (R3)mrepresents m substituents R3,
    • where, in the case that m=1, the substituent radical R3or, in the case that m is greater than 1, each of the substituents R3independently of one another represents fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, methoxy, (here preferably 2-methoxy, 3-methoxy), methylthio, methylsulfinyl, methylsulfonyl, trifluoromethyl, trifluoromethoxy, trifluoroalkylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, and
      m represents 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, and
      n represents 0, 1, 2 or 3, preferably 0, 1 or 2,
      and also preferably
  • R1is hydrogen or a group selected from the group consisting of: acetyl, propanoyl, butanoyl, pentanoyl, hexanoyl, 2-methylpropanoyl (=isopropanoyl), 2,2-difluoroacetyl, 2,2,2-trifluoroacetyl, C(═O)OMe, cyclopropanecarbonyl, 1-methylcyclopropanecarbonyl, acryl, prop-2-ynoyl, but-2-ynoyl, 2-methylacryl, benzoyl, 4-chlorobenzoyl, 3-chlorobenzoyl, 2-chlorobenzoyl, 4-fluorobenzoyl, 3-fluorobenzoyl, 2-fluorobenzoyl, 2,2-dimethylpropanoyl (=pivaloyl), 3,3-dimethylbutanoyl and 2-nitrobenzoyl.

[0176]

Particular preference is given to compounds of the formula (I) according to the invention or salts thereof or of the formula (Ia) defined below or salts thereof, in which

  • (R2)nrepresents n substituents R2, where, in the case that n=1, the substituent R2or, in the case that n is greater than 1, each of the substituents R2independently of the others is fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, or methoxy.

[0178]

Particular preference is given to compounds of the formula (I) according to the invention or salts thereof or of the formula (Ia) defined below or salts thereof, in which

  • (R3)mrepresents m substituents R3, 2-bromo, 3-bromo, 4-bromo, 2-chloro, 3-chloro, 4-chloro, 2-fluoro, 3-fluoro, 4-fluoro, 2-cyano, 3-cyano, 4-cyano, 2-methyl, 3-methyl, 4-methyl, 2-ethyl, 3-ethyl, 4-ethyl, 2-CF3, 3-CF3, 4-CF3, 2-methoxy, 3-methoxy, 4-methoxy, 2-ethoxy, 3-ethoxy, 4-ethoxy, 2-methylthio, 3-methylthio, 4-methylthio, 2-methylsulfinyl, 3-methylsulfinyl, 4-methylsulfinyl, 2-methylsulfonyl, 3-methylsulfonyl, 4-methylsulfonyl, 2-nitro, 3-nitro, 4-nitro, 2,3-dimethyl, 2,4-dimethyl, 2,5-dimethyl, 2,6-dimethyl, 3,4-dimethyl, 3,5-dimethyl, 2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, 2,3-dichloro, 2,4-dichloro, 2,5-dichloro, 2,6-dichloro, 3,4-dichloro, 3,5-dichloro, 2,5-dicyano, 2,6-dicyano, (2-Cl-3-F), (2-Cl-4-F), (2-Cl-5-F), (2-Cl-6-F), (3-Cl-2-F), (3-Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F), (4-Cl-3-F), (4-Br-2-F), (4-Br-3-F), (4-CN-3-F), (4-NO2-3-F), (4-OMe-3-F), (3-CN-4-F), (3-NO2-4-F), (3-CN-4-Cl), (3-NO2-4-Cl), (S—CN-2-F), 2,3,4-trifluoro, 2,3,5-trifluoro, 2,3,6-trifluoro, 2,4,6-trifluoro, 3,4,5-trifluoro, 2,3,4-trichloro, 2,3,5-trichloro, 2,3,6-trichloro, 2,4,6-trichloro, 3,4,5-trichloro or (2,6-F2-4-Cl).

[0180]

Preferred compounds according to the invention are compounds of the formula (Ia) shown below, (corresponding to compounds of the formula (I) in which the radical R1=hydrogen), their salts and their esters

[0000]

[0000]

in which Q, R2, R3, m and n in each case have the meanings given above and below, with preference the meanings stated as preferred, preferably the meanings stated as preferred, particularly preferably the meanings stated as preferred, and especially (preferably) the meanings stated as especially (preferred).

[0181]

In a preferred embodiment of the present invention, m+n>0, i.e. preferably at least one of the radicals R2and R3does not represent hydrogen.

[0182]

Preference according to the invention is given to compounds of the formula (I) or (Ia) or salts thereof in which n>0.

[0183]

Preference according to the invention is likewise given to compounds of the formula (I) or (Ia) or salts thereof in which m>0.

[0184]

In a preferred embodiment of the present invention, m+n>1, i.e. preferably at least two radicals R2, at least two radicals R3or at least one radical R2and at least one radical R3do not represent hydrogen.

[0185]

In preferred compounds of the formula (I) or (Ia) according to the invention or salts thereof, the sum of m+n=2, 3, 4 or 5.

[0186]

In particularly preferred compounds of the formula (I) or (Ia) according to the invention, n is greater than or equal to 1 and one or more radicals R2represent halogen, preferably halogen selected from the group consisting of F, Cl and Br.

[0187]

In particularly preferred compounds of the formula (I) or (Ia) according to the invention, m is greater than or equal to 1 and one or more radicals R3represent halogen, preferably halogen from the group consisting of F, Cl and Br.

[0188]

Particularly preferred compounds of the formula (Ia) according to the invention correspond to the above-defined formula (I-2), in which R1=hydrogen.

[0189]

Particular preference is likewise given to compounds of the formula (I) according to the invention or salts thereof in which

[0000]

(R2)nrepresents n substituents R2,

    • where, in the case that n=1, the substituent R2or, in the case that n is greater than 1, each of the substituents R2independently of the others is fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, or methoxy,
  • (R3)mrepresents m substituents R3, where, in the case that m=1, the substituent radical R3or, in the case that m is greater than 1, each of the substituents R3independently of the others is 2-bromo, 3-bromo, 4-bromo, 2-chloro, 3-chloro, 4-chloro, 2-fluoro, 3-fluoro, 4-fluoro, 2-cyano, 3-cyano, 4-cyano, 2-methyl, 3-methyl, 4-methyl, 2-ethyl, 3-ethyl, 4-ethyl, 2-CF3, 3-CF3, 4-CF3, 2-methoxy, 3-methoxy, 4-methoxy, 2-ethoxy, 3-ethoxy, 4-ethoxy, 2-methylthio, 3-methylthio, 4-methylthio, 2-methylsulfinyl, 3-methylsulfinyl, 4-methylsulfinyl, 2-methylsulfonyl, 3-methylsulfonyl, 4-methylsulfonyl, 2-nitro, 3-nitro, 4-nitro, 2,3-dimethyl, 2,4-dimethyl, 2,5-dimethyl, 2,6-dimethyl, 3,4-dimethyl, 3,5-dimethyl, 2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, 2,3-dichloro, 2,4-dichloro, 2,5-dichloro, 2,6-dichloro, 3,4-dichloro, 3,5-dichloro, 2,5-dicyano, 2,6-dicyano, (2-Cl-3-F), (2-Cl-4-F), (2-Cl-5-F), (2-Cl-6-F), (3-Cl-2-F), (3-Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F), (4-Cl-3-F), (4-Br-2-F), (4-Br-3-F), (4-CN-3-F), (4-NO2-3-F), (4-OMe-3-F), (3-CN-4-F), (3-NO2-4-F), (3-CN-4-Cl), (3-NO2-4-Cl), (5-CN-2-F), 2,3,4-trifluoro, 2,3,5-trifluoro, 2,3,6-trifluoro, 2,4,6-trifluoro, 3,4,5-trifluoro, 2,3,4-trichloro, 2,3,5-trichloro, 2,3,6-trichloro, 2,4,6-trichloro, 3,4,5-trichloro or (2,6-F2-4-Cl),
  • R1is hydrogen or a group selected from the group consisting of: acetyl, propanoyl, butanoyl, pentanoyl, hexanoyl, 2-methylpropanoyl (=isopropanoyl), 2,2-difluoroacetyl, 2,2,2-trifluoroacetyl, C(═O)OMe, cyclopropanecarbonyl, 1-methylcyclopropanecarbonyl, acryl, prop-2-ynoyl, but-2-ynoyl, 2-methylacryl, benzoyl, 4-chlorobenzoyl, 3-chlorobenzoyl, 2-chlorobenzoyl, 4-fluorobenzoyl, 3-fluorobenzoyl, 2-fluorobenzoyl, 2,2-dimethylpropanoyl (=pivaloyl), 3,3-dimethylbutanoyl and 2-nitrobenzoyl,
    m is 0, 1, 2 or 3, and
    n is 0, 1 or 2,
    where preferably the sum of m+n=2, 3, 4, or 5.

[0193]

Preferred compounds according to the invention are compounds of the formula (I) or (Ia), in which Q(R2)nhas the meaning given in Tables 1 to 3 below. Here, in turn, preference is given to compounds of the formula (I) or (Ia) according to the invention, in which Q(R2)nhas the meaning given in Tables 2 to 3 below.

[0194]

Preferred compounds according to the invention are compounds of the formula (I) or (Ia), in which (R3)nhas the meaning given in Tables 1 to 3 below.

[0195]

Preferred compounds according to the invention are compounds of the formula (I) as defined in Tables 1 to 3 below.

[0196]

Tables 1 to 3 below give preferred meanings of Q(R2)nand (R3)mand R1. The abbreviations and annotations used herein are explained in the Example Section.

[0000]

Preferred meanings of Q(R2)n, (R3)mand R1in
compounds of the formula (I) according to the invention
No.Q(R2)n(R3)mR1
16-fluoropyridin-3-yl2.6-F2H
26-chloropyridin-3-yl2.6-F2H
36-bromopyridin-3-yl2.6-F2H
45-fluoropyridin-3-yl2.6-F2H
55-chloropyridin-3-yl2.6-F2H
65-bromopyridin-3-yl2.6-F2H
74-fluoropyridin-3-yl2.6-F2H
84-chloropyridin-3-yl2.6-F2H
94-bromopyridin-3-yl2.6-F2H
102-fluoropyridin-3-yl2.6-F2H
112-chloropyridin-3-yl2.6-F2H
122-bromopyridin-3-yl2.6-F2H
132,6-difluoropyridin-3-yl2.6-F2H
145-chloro-6-fluoropyridin-3-yl2.6-F2H
155-bromo-6-fluoropyridin-3-yl2.6-F2H
165,6-difluoropyridin-3-yl2.6-F2H
176-chloro-5-fluoropyridin-3-yl2.6-F2H
186-bromo-5-fluoropyridin-3-yl2.6-F2H
194,5-difluoropyridin-3-yl2.6-F2H
204-chloro-5-fluoropyridin-3-yl2.6-F2H
214-bromo-5-fluoropyridin-3-yl2.6-F2H
225-chloro-4-fluoropyridin-3-yl2.6-F2H
234,5-dichloropyridin-3-yl2.6-F2H
244-bromo-5-chloropyridin-3-yl2.6-F2H
255-bromo-4-fluoropyridin-3-yl2.6-F2H
265-bromo-4-chloropyridin-3-yl2.6-F2H
274,5-dibromopyridin-3-yl2.6-F2H
282,3-difluoropyridin-4-yl2.6-F2H
293-chloro-2-fluoropyridin-4-yl2.6-F2H
303-bromo-2-fluoropyridin-4-yl2.6-F2H
312-fluoropyridin-4-yl2.6-F2H
322-chloropyridin-4-yl2.6-F2H
332-bromopyridin-4-yl2.6-F2H
342,6-difluoropyridin-4-yl2.6-F2H
352-chloro-6-fluoropyridin-4-yl2.6-F2H
362-bromo-6-fluoropyridin-4-yl2.6-F2H
372,3,6-trifluoropyridin-4-yl2.6-F2H
383-chloro-2,6-difluoropyridin-4-yl2.6-F2H
393-bromo-2,6-difluoropyridin-4-yl2.6-F2H
402-chloro-3,6-difluoropyridin-4-yl2.6-F2H
412-bromo-3,6-difluoropyridin-4-yl2.6-F2H
426-chloro-2,3-difluoropyridin-4-yl2.6-F2H
436-bromo-2,3-difluoropyridin-4-yl2.6-F2H
442,5,6-trifluoropyridin-3-yl2.6-F2H
452-chloro-5,6-difluoropyridin-3-yl2.6-F2H
462-bromo-5,6-difluoropyridin-3-yl2.6-F2H
476-chloro-2,5-difluoropyridin-3-yl2.6-F2H
486-bromo-2,5-difluoropyridin-3-yl2.6-F2H
495-chloro-2,6-difluoropyridin-3-yl2.6-F2H
505-bromo-2,6-difluoropyridin-3-yl2.6-F2H
516-fluoropyridin-2-yl2.6-F2H
526-chloropyridin-2-yl2.6-F2H
536-bromopyridin-2-yl2.6-F2H
545-fluoropyridin-2-yl2.6-F2H
555-chloropyridin-2-yl2.6-F2H
565-bromopyridin-2-yl2.6-F2H
574-fluoropyridin-2-yl2.6-F2H
584-chloropyridin-2-yl2.6-F2H
594-bromopyridin-2-yl2.6-F2H
603-fluoropyridin-2-yl2.6-F2H
613-chloropyridin-2-yl2.6-F2H
623-bromopyridin-2-yl2.6-F2H
633,4-difluoropyridin-2-yl2.6-F2H
644-chloro-3-fluoropyridin-2-yl2.6-F2H
654-bromo-3-fluoropyridin-2-yl2.6-F2H
663,5-difluoropyridin-2-yl2.6-F2H
675-chloro-3-fluoropyridin-2-yl2.6-F2H
685-bromo-3-fluoropyridin-2-yl2.6-F2H
693,6-difluoropyridin-2-yl2.6-F2H
706-chloro-3-fluoropyridin-2-yl2.6-F2H
716-bromo-3-fluoropyridin-2-yl2.6-F2H
723,4,6-trifluoropyridin-2-yl2.6-F2H
734-chloro-3,6-difluoropyridin-2-yl2.6-F2H
744-bromo-3,6-difluoropyridin-2-yl2.6-F2H
753,5,6-trifluoropyridin-2-yl2.6-F2H
765-chloro-3,6-difluoropyridin-2-yl2.6-F2H
775-bromo-3,6-difluoropyridin-2-yl2.6-F2H
784,5,6-trifluoropyridin-3-yl2.6-F2H
794-chloro-5,6-difluoropyridin-3-yl2.6-F2H
804-bromo-5,6-difluoropyridin-3-yl2.6-F2H
815-chloro-4,6-difluoropyridin-3-yl2.6-F2H
825-bromo-4,6-difluoropyridin-3-yl2.6-F2H
836-chloro-4,5-difluoropyridin-3-yl2.6-F2H
846-bromo-4,5-difluoropyridin-3-yl2.6-F2H
85pyridin-3-yl2.6-F2H
86pyridin-2-yl2.6-F2H
87pyridin-4-yl2.6-F2H
882-fluoropyrimidin-4-yl2.6-F2H
892-chloropyrimidin-4-yl2.6-F2H
902-bromopyrimidin-4-yl2.6-F2H
912,6-difluoropyrimidin-4-yl2.6-F2H
926-chloro-2-fluoropyrimidin-4-yl2.6-F2H
936-bromo-2-fluoropyrimidin-4-yl2.6-F2H
946-fluoropyrimidin-4-yl2.6-F2H
956-chloropyrimidin-4-yl2.6-F2H
966-bromopyrimidin-4-yl2.6-F2H
974-fluoropyrimidin-2-yl2.6-F2H
984-chloropyrimidin-2-yl2.6-F2H
994-bromopyrimidin-2-yl2.6-F2H
1004,5-difluoropyrimidin-2-yl2.6-F2H
1015-chloro-4-fluoropyrimidin-2-yl2.6-F2H
1025-bromo-4-fluoropyrimidin-2-yl2.6-F2H
1034-chloro-5-fluoropyrimidin-2-yl2.6-F2H
1044-bromo-5-fluoropyrimidin-2-yl2.6-F2H
1054,6-difluoropyrimidin-2-yl2.6-F2H
1064-chloro-6-fluoropyrimidin-2-yl2.6-F2H
1074-bromo-6-fluoropyrimidin-2-yl2.6-F2H
108pyrimidin-2-yl2.6-F2H
109pyrimidin-4-yl2.6-F2H
110pyrimidin-5-yl2.6-F2H
1112,4-difluoropyrimidin-5-yl2.6-F2H
1124-chloro-2-fluoropyrimidin-5-yl2.6-F2H
1134-bromo-2-fluoropyrimidin-5-yl2.6-F2H
1142-fluoropyrimidin-5-yl2.6-F2H
1152-chloropyrimidin-5-yl2.6-F2H
1162-bromopyrimidin-5-yl2.6-F2H
117pyridazin-3-yl2.6-F2H
118pyridazin-4-yl2.6-F2H
1196-fluoropyridazin-4-yl2.6-F2H
1206-chloropyridazin-4-yl2.6-F2H
1216-bromopyridazin-4-yl2.6-F2H
1225,6-difluoropyridazin-4-yl2.6-F2H
1235-chloro-6-fluoropyridazin-4-yl2.6-F2H
1245-bromo-6-fluoropyridazin-4-yl2.6-F2H
1256-chloro-5-fluoropyridazin-4-yl2.6-F2H
1266-bromo-5-fluoropyridazin-4-yl2.6-F2H
1273,5-difluoropyridazin-4-yl2.6-F2H
1283-chloro-5-fluoropyridazin-4-yl2.6-F2H
1293-bromo-5-fluoropyridazin-4-yl2.6-F2H
1305-chloro-3-fluoropyridazin-4-yl2.6-F2H
1315-bromo-3-fluoropyridazin-4-yl2.6-F2H
1323,6-difluoropyridazin-4-yl2.6-F2H
1336-chloro-3-fluoropyridazin-4-yl2.6-F2H
1346-bromo-3-fluoropyridazin-4-yl2.6-F2H
1353-chloro-6-fluoropyridazin-4-yl2.6-F2H
1363-bromo-6-fluoropyridazin-4-yl2.6-F2H
1376-fluoropyridazin-3-yl2.6-F2H
1386-chloropyridazin-3-yl2.6-F2H
1396-bromopyridazin-3-yl2.6-F2H
1405-fluoropyridazin-3-yl2.6-F2H
1415-chloropyridazin-3-yl2.6-F2H
1425-bromopyridazin-3-yl2.6-F2H
1434-fluoropyridazin-3-yl2.6-F2H
1444-chloropyridazin-3-yl2.6-F2H
1454-bromopyridazin-3-yl2.6-F2H
1465,6-difluoropyridazin-3-yl2.6-F2H
1475-chloro-6-fluoropyridazin-3-yl2.6-F2H
1485-bromo-6-fluoropyridazin-3-yl2.6-F2H
1496-chloro-5-fluoropyridazin-3-yl2.6-F2H
1506-bromo-5-fluoropyridazin-3-yl2.6-F2H
1514,6-difluoropyridazin-3-yl2.6-F2H
1524-chloro-6-fluoropyridazin-3-yl2.6-F2H
1534-bromo-6-fluoropyridazin-3-yl2.6-F2H
1546-chloro-4-fluoropyridazin-3-yl2.6-F2H
1556-bromo-4-fluoropyridazin-3-yl2.6-F2H
1564,5-difluoropyridazin-3-yl2.6-F2H
1575-chloro-4-fluoropyridazin-3-yl2.6-F2H
1585-bromo-4-fluoropyridazin-3-yl2.6-F2H
1594-chloro-5-fluoropyridazin-3-yl2.6-F2H
1604-bromo-5-fluoropyridazin-3-yl2.6-F2H
161pyrazin-2-yl2.6-F2H
1623-fluoropyrazin-2-yl2.6-F2H
1633-chloropyrazin-2-yl2.6-F2H
1643-bromopyrazin-2-yl2.6-F2H
1656-fluoropyrazin-2-yl2.6-F2H
1666-chloropyrazin-2-yl2.6-F2H
1676-bromopyrazin-2-yl2.6-F2H
1685-fluoropyrazin-2-yl2.6-F2H
1695-chloropyrazin-2-yl2.6-F2H
1705-bromopyrazin-2-yl2.6-F2H
1715,6-difluoropyrazin-2-yl2.6-F2H
1725-chloro-6-fluoropyrazin-2-yl2.6-F2H
1735-bromo-6-fluoropyrazin-2-yl2.6-F2H
1746-chloro-5-fluoropyrazin-2-yl2.6-F2H
1756-bromo-5-fluoropyrazin-2-yl2.6-F2H
1763,5-difluoropyrazin-2-yl2.6-F2H
1773-chloro-5-fluoropyrazin-2-yl2.6-F2H
1783-bromo-5-fluoropyrazin-2-yl2.6-F2H
1795-chloro-3-fluoropyrazin-2-yl2.6-F2H
1805-bromo-3-fluoropyrazin-2-yl2.6-F2H
1813,6-difluoropyrazin-2-yl2.6-F2H
1826-chloro-3-fluoropyrazin-2-yl2.6-F2H
1836-bromo-3-fluoropyrazin-2-yl2.6-F2H
1843-chloro-6-fluoropyrazin-2-yl2.6-F2H
1853-bromo-6-fluoropyrazin-2-yl2.6-F2H
1862-thienyl2.6-F2H
1875-fluoro-2-thienyl2.6-F2H
1885-chloro-2-thienyl2.6-F2H
1895-bromo-2-thienyl2.6-F2H
1904-fluoro-2-thienyl2.6-F2H
1914-chloro-2-thienyl2.6-F2H
1924-bromo-2-thienyl2.6-F2H
1932-fluoro-2-thienyl2.6-F2H
1943-chloro-2-thienyl2.6-F2H
1953-bromo-2-thienyl2.6-F2H
1963-thienyl2.6-F2H
1972-fluoro-3-thienyl2.6-F2H
1982-chloro-3-thienyl2.6-F2H
1992-bromo-3-thienyl2.6-F2H
2005-fluoro-3-thienyl2.6-F2H
2015-chloro-3-thienyl2.6-F2H
2025-bromo-3-thienyl2.6-F2H
2034-fluoro-3-thienyl2.6-F2H
2044-chloro-3-thienyl2.6-F2H
2054-bromo-3-thienyl2.6-F2H
2062,4-difluoro-3-thienyl2.6-F2H
2072-chloro-4-fluoro-3-thienyl2.6-F2H
2082-bromo-4-fluoro-3-thienyl2.6-F2H
2094-chloro-2-fluoro-3-thienyl2.6-F2H
2104-bromo-2-fluoro-3-thienyl2.6-F2H
2112,5-difluoro-3-thienyl2.6-F2H
2125-chloro-2-fluoro-3-thienyl2.6-F2H
2135-bromo-2-fluoro-3-thienyl2.6-F2H
2142-chloro-5-fluoro-3-thienyl2.6-F2H
2152-bromo-5-fluoro-3-thienyl2.6-F2H
2164,5-difluoro-3-thienyl2.6-F2H
2174-chloro-5-fluoro-3-thienyl2.6-F2H
2184-bromo-5-fluoro-3-thienyl2.6-F2H
2195-chloro-4-fluoro-3-thienyl2.6-F2H
2205-bromo-4-fluoro-3-thienyl2.6-F2H
2213,4-difluoro-2-thienyl2.6-F2H
2224-chloro-3-fluoro-2-thienyl2.6-F2H
2234-bromo-3-fluoro-2-thienyl2.6-F2H
2243-chloro-4-fluoro-2-thienyl2.6-F2H
2253-bromo-4-fluoro-2-thienyl2.6-F2H
2263,5-difluoro-2-thienyl2.6-F2H
2275-chloro-3-fluoro-2-thienyl2.6-F2H
2285-bromo-3-fluoro-2-thienyl2.6-F2H
2293-chloro-5-fluoro-2-thienyl2.6-F2H
2303-bromo-5-fluoro-2-thienyl2.6-F2H
2314,5-difluoro-2-thienyl2.6-F2H
2324-chloro-5-fluoro-2-thienyl2.6-F2H
2334-bromo-5-fluoro-2-thienyl2.6-F2H
2345-chloro-4-fluoro-2-thienyl2.6-F2H
2355-bromo-4-fluoro-2-thienyl2.6-F2H
2362-furyl2.6-F2H
2375-fluoro-2-furyl2.6-F2H
2385-chloro-2-furyl2.6-F2H
2395-bromo-2-furyl2.6-F2H
2404-fluoro-2-furyl2.6-F2H
2414-chloro-2-furyl2.6-F2H
2424-bromo-2-furyl2.6-F2H
2432-fluoro-2-furyl2.6-F2H
2443-chloro-2-furyl2.6-F2H
2453-bromo-2-furyl2.6-F2H
2463-furyl2.6-F2H
2472-fluoro-3-furyl2.6-F2H
2482-chloro-3-furyl2.6-F2H
2492-bromo-3-furyl2.6-F2H
2505-fluoro-3-furyl2.6-F2H
2515-chloro-3-furyl2.6-F2H
2525-bromo-3-furyl2.6-F2H
2534-fluoro-3-furyl2.6-F2H
2544-chloro-3-furyl2.6-F2H
2554-bromo-3-furyl2.6-F2H
2562,4-difluoro-3-furyl2.6-F2H
2572-chloro-4-fluoro-3-furyl2.6-F2H
2582-bromo-4-fluoro-3-furyl2.6-F2H
2594-chloro-2-fluoro-3-furyl2.6-F2H
2604-bromo-2-fluoro-3-furyl2.6-F2H
2612,5-difluoro-3-furyl2.6-F2H
2625-chloro-2-fluoro-3-furyl2.6-F2H
2635-bromo-2-fluoro-3-furyl2.6-F2H
2642-chloro-5-fluoro-3-furyl2.6-F2H
2652-bromo-5-fluoro-3-furyl2.6-F2H
2664,5-difluoro-3-furyl2.6-F2H
2674-chloro-5-fluoro-3-furyl2.6-F2H
2684-bromo-5-fluoro-3-furyl2.6-F2H
2695-chloro-4-fluoro-3-furyl2.6-F2H
2705-bromo-4-fluoro-3-furyl2.6-F2H
2713,4-difluoro-2-furyl2.6-F2H
2724-chloro-3-fluoro-2-furyl2.6-F2H
2734-bromo-3-fluoro-2-furyl2.6-F2H
2743-chloro-4-fluoro-2-furyl2.6-F2H
2753-bromo-4-fluoro-2-furyl2.6-F2H
2763,5-difluoro-2-furyl2.6-F2H
2775-chloro-3-fluoro-2-furyl2.6-F2H
2785-bromo-3-fluoro-2-furyl2.6-F2H
2793-chloro-5-fluoro-2-furyl2.6-F2H
2803-bromo-5-fluoro-2-furyl2.6-F2H
2814,5-difluoro-2-furyl2.6-F2H
2824-chloro-5-fluoro-2-furyl2.6-F2H
2834-bromo-5-fluoro-2-furyl2.6-F2H
2845-chloro-4-fluoro-2-furyl2.6-F2H
2855-bromo-4-fluoro-2-furyl2.6-F2H
2861,3-oxazol-2-yl2.6-F2H
2871,3-oxazol-5-yl2.6-F2H
2881,3-oxazol-4-yl2.6-F2H
2892-fluoro-1,3-oxazol-4-yl2.6-F2H
2902-chloro-1,3-oxazol-4-yl2.6-F2H
2912-bromo-1,3-oxazol-4-yl2.6-F2H
2922,5-difluoro-1,3-oxazol-4-yl2.6-F2H
2935-chloro-2-fluoro-1,3-oxazol-4-yl2.6-F2H
2945-bromo-2-fluoro-1,3-oxazol-4-yl2.6-F2H
2952-chloro-5-fluoro-1,3-oxazol-4-yl2.6-F2H
2962-bromo-5-fluoro-1,3-oxazol-4-yl2.6-F2H
2975-fluoro-1,3-oxazol-2-yl2.6-F2H
2985-chloro-1,3-oxazol-2-yl2.6-F2H
2995-bromo-1,3-oxazol-2-yl2.6-F2H
3004,5-difluoro-1,3-oxazol-2-yl2.6-F2H
3014-chloro-5-fluoro-1,3-oxazol-2-yl2.6-F2H
3024-bromo-5-fluoro-1,3-oxazol-2-yl2.6-F2H
3035-chloro-4-fluoro-1,3-oxazol-2-yl2.6-F2H
3045-bromo-4-fluoro-1,3-oxazol-2-yl2.6-F2H
3052-fluoro-1,3-oxazol-5-yl2.6-F2H
3062-chloro-1,3-oxazol-5-yl2.6-F2H
3072-bromo-1,3-oxazol-5-yl2.6-F2H
3082,4-difluoro-1,3-oxazol-5-yl2.6-F2H
3094-chloro-2-fluoro-1,3-oxazol-5-yl2.6-F2H
3104-bromo-2-fluoro-1,3-oxazol-5-yl2.6-F2H
3112-chloro-4-fluoro-1,3-oxazol-5-yl2.6-F2H
3122-bromo-4-fluoro-1,3-oxazol-5-yl2.6-F2H
3131,3-thiazol-2-yl2.6-F2H
3141,3-thiazol-5-yl2.6-F2H
3151,3-thiazol-4-yl2.6-F2H
3162-fluoro-1,3-thiazol-4-yl2.6-F2H
3172-chloro-1,3-thiazol-4-yl2.6-F2H
3182-bromo-1,3-thiazol-4-yl2.6-F2H
3192,5-difluoro-1,3-thiazol-4-yl2.6-F2H
3205-chloro-2-fluoro-1,3-thiazol-4-yl2.6-F2H
3215-bromo-2-fluoro-1,3-thiazol-4-yl2.6-F2H
3222-chloro-5-fluoro-1,3-thiazol-4-yl2.6-F2H
3232-bromo-5-fluoro-1,3-thiazol-4-yl2.6-F2H
3245-fluoro-1,3-thiazol-2-yl2.6-F2H
3255-chloro-1,3-thiazol-2-yl2.6-F2H
3265-bromo-1,3-thiazol-2-yl2.6-F2H
3274,5-difluoro-1,3-thiazol-2-yl2.6-F2H
3284-chloro-5-fluoro-1,3-thiazol-2-yl2.6-F2H
3294-bromo-5-fluoro-1,3-thiazol-2-yl2.6-F2H
3305-chloro-4-fluoro-1,3-thiazol-2-yl2.6-F2H
3315-bromo-4-fluoro-1,3-thiazol-2-yl2.6-F2H
3322-fluoro-1,3-thiazol-5-yl2.6-F2H
3332-chloro-1,3-thiazol-5-yl2.6-F2H
3342-bromo-1,3-thiazol-5-yl2.6-F2H
3352,4-difluoro-1,3-thiazol-5-yl2.6-F2H
3364-chloro-2-fluoro-1,3-thiazol-5-yl2.6-F2H
3374-bromo-2-fluoro-1,3-thiazol-5-yl2.6-F2H
3382-chloro-4-fluoro-1,3-thiazol-5-yl2.6-F2H
3392-bromo-4-fluoro-1,3-thiazol-5-yl2.6-F2H
3401-methyl-1H-imidazol-2-yl2.6-F2H
3411-methyl-1H-imidazol-5-yl2.6-F2H
3421-methyl-1H-imidazol-4-yl2.6-F2H
3432-fluoro-1,3-1-methyl-1H-imidazol-4-yl2.6-F2H
3442-chloro-1,3-1-methyl-1H-imidazol-4-yl2.6-F2H
3452-bromo-1,3-1-methyl-1H-imidazol-4-yl2.6-F2H
3462,5-difluoro-1,3-1-methyl-1H-imidazol-4-yl2.6-F2H
3475-chloro-2-fluoro-1,3-1-methyl-1H-imidazol-4-2.6-F2H
yl
3485-bromo-2-fluoro-1,3-1-methyl-1H-imidazol-4-2.6-F2H
yl
3492-chloro-5-fluoro-1,3-1-methyl-1H-imidazol-4-2.6-F2H
yl
3502-bromo-5-fluoro-1,3-1-methyl-1H-imidazol-4-2.6-F2H
yl
3515-fluoro-1,3-1-methyl-1H-imidazol-2-yl2.6-F2H
3525-chloro-1,3-1-methyl-1H-imidazol-2-yl2.6-F2H
3535-bromo-1,3-1-methyl-1H-imidazol-2-yl2.6-F2H
3544,5-difluoro-1,3-1-methyl-1H-imidazol-2-yl2.6-F2H
3554-chloro-5-fluoro-1,3-1-methyl-1H-imidazol-2-2.6-F2H
yl
3564-bromo-5-fluoro-1,3-1-methyl-1H-imidazol-2-2.6-F2H
yl
3575-chloro-4-fluoro-1,3-1-methyl-1H-imidazol-2-2.6-F2H
yl
3585-bromo-4-fluoro-1,3-1-methyl-1H-imidazol-2-2.6-F2H
yl
3592-fluoro-1,3-1-methyl-1H-imidazol-5-yl2.6-F2H
3602-chloro-1,3-1-methyl-1H-imidazol-5-yl2.6-F2H
3612-bromo-1,3-1-methyl-1H-imidazol-5-yl2.6-F2H
3622,4-difluoro-1,3-1-methyl-1H-imidazol-5-yl2.6-F2H
3634-chloro-2-fluoro-1,3-1-methyl-1H-imidazol-5-2.6-F2H
yl
3644-bromo-2-fluoro-1,3-1-methyl-1H-imidazol-5-2.6-F2H
yl
3652-chloro-4-fluoro-1,3-1-methyl-1H-imidazol-5-2.6-F2H
yl
3662-bromo-4-fluoro-1,3-1-methyl-1H-imidazol-5-2.6-F2H
yl
3671-methyl-1H-pyrazol-5-yl2.6-F2H
3683-fluoro-1-methyl-1H-pyrazol-5-yl2.6-F2H
3693-chloro-1-methyl-1H-pyrazol-5-yl2.6-F2H
3703-bromo-1-methyl-1H-pyrazol-5-yl2.6-F2H
3714-fluoro-1-methyl-1H-pyrazol-5-yl2.6-F2H
3724-chloro-1-methyl-1H-pyrazol-5-yl2.6-F2H
3734-bromo-1-methyl-1H-pyrazol-5-yl2.6-F2H
3743,4-difluoro-1-methyl-1H-pyrazol-5-yl2.6-F2H
3754-chloro-3-fluoro-1-methyl-1H-pyrazol-5-yl2.6-F2H
3764-bromo-3-fluoro-1-methyl-1H-pyrazol-5-yl2.6-F2H
3773-chloro-4-fluoro-1-methyl-1H-pyrazol-5-yl2.6-F2H
3783-bromo-4-fluoro-1-methyl-1H-pyrazol-5-yl2.6-F2H
3791-methyl-1H-pyrazol-4-yl2.6-F2H
3805-fluoro-1-methyl-1H-pyrazol-4-yl2.6-F2H
3815-chloro-1-methyl-1H-pyrazol-4-yl2.6-F2H
3825-bromo-1-methyl-1H-pyrazol-4-yl2.6-F2H
3833-fluoro-1-methyl-1H-pyrazol-4-yl2.6-F2H
3843-chloro-1-methyl-1H-pyrazol-4-yl2.6-F2H
3853-bromo-1-methyl-1H-pyrazol-4-yl2.6-F2H
3863,5-difluoro-1-methyl-1H-pyrazol-4-yl2.6-F2H
3875-chloro-3-fluoro-1-methyl-1H-pyrazol-4-yl2.6-F2H
3885-bromo-3-fluoro-1-methyl-1H-pyrazol-4-yl2.6-F2H
3893-chloro-5-fluoro-1-methyl-1H-pyrazol-4-yl2.6-F2H
3903-bromo-5-fluoro-1-methyl-1H-pyrazol-4-yl2.6-F2H
3915-fluoro-1-methyl-1H-pyrazol-3-yl2.6-F2H
3925-chloro-1-methyl-1H-pyrazol-3-yl2.6-F2H
3935-bromo-1-methyl-1H-pyrazol-3-yl2.6-F2H
3944-fluoro-1-methyl-1H-pyrazol-3-yl2.6-F2H
3954-chloro-1-methyl-1H-pyrazol-3-yl2.6-F2H
3964-bromo-1-methyl-1H-pyrazol-3-yl2.6-F2H
3974,5-difluoro-1-methyl-1H-pyrazol-3-yl2.6-F2H
3984-chloro-5-fluoro-1-methyl-1H-pyrazol-3-yl2.6-F2H
3994-bromo-5-fluoro-1-methyl-1H-pyrazol-3-yl2.6-F2H
4005-chloro-4-fluoro-1-methyl-1H-pyrazol-3-yl2.6-F2H
4015-bromo-4-fluoro-1-methyl-1H-pyrazol-3-yl2.6-F2H
4021,3,5-triazin-2-yl2.6-F2H
4034-fluoro-1,3,5-triazin-2-yl2.6-F2H
4044-chloro-1,3,5-triazin-2-yl2.6-F2H
4054-bromo-1,3,5-triazin-2-yl2.6-F2H
4064,6-difluoro-1,3,5-triazin-2-yl2.6-F2H
4074-chloro-6-fluoro-1,3,5-triazin-2-yl2.6-F2H
4084-bromo-6-fluoro-1,3,5-triazin-2-yl2.6-F2H
4091,2,3-triazin-4-yl2.6-F2H
4106-fluoro-1,2,3-triazin-4-yl2.6-F2H
4116-chloro-1,2,3-triazin-4-yl2.6-F2H
4126-bromo-1,2,3-triazin-4-yl2.6-F2H
4135,6-difluoro-1,2,3-triazin-4-yl2.6-F2H
4145-chloro-6-fluoro-1,2,3-triazin-4-yl2.6-F2H
4155-bromo-6-fluoro-1,2,3-triazin-4-yl2.6-F2H
4161,2,3-triazin-5-yl2.6-F2H
4174-fluoro-1,2,3-triazin-5-yl2.6-F2H
4184-chloro-1,2,3-triazin-5-yl2.6-F2H
4194-bromo-1,2,3-triazin-5-yl2.6-F2H
4204,6-difluoro-1,2,3-triazin-5-yl2.6-F2H
4214-chloro-6-fluoro-1,2,3-triazin-5-yl2.6-F2H
4224-bromo-6-fluoro-1,2,3-triazin-5-yl2.6-F2H
4231,2,4-triazin-5-yl2.6-F2H
4243-fluoro-1,2,4-triazin-5-yl2.6-F2H
4253-chloro-1,2,4-triazin-5-yl2.6-F2H
4263-bromo-1,2,4-triazin-5-yl2.6-F2H
4276-fluoro-1,2,4-triazin-5-yl2.6-F2H
4286-chloro-1,2,4-triazin-5-yl2.6-F2H
4296-bromo-1,2,4-triazin-5-yl2.6-F2H
4303,6-difluoro-1,2,4-triazin-5-yl2.6-F2H
4316-chloro-3-fluoro-1,2,4-triazin-5-yl2.6-F2H
4326-bromo-3-fluoro-1,2,4-triazin-5-yl2.6-F2H
4333-chloro-6-fluoro-1,2,4-triazin-5-yl2.6-F2H
4343-bromo-6-fluoro-1,2,4-triazin-5-yl2.6-F2H
4351,2,4-triazin-3-yl2.6-F2H
4366-fluoro-1,2,4-triazin-3-yl2.6-F2H
4376-chloro-1,2,4-triazin-3-yl2.6-F2H
4386-bromo-1,2,4-triazin-3-yl2.6-F2H
4395-fluoro-1,2,4-triazin-3-yl2.6-F2H
4405-chloro-1,2,4-triazin-3-yl2.6-F2H
4415-bromo-1,2,4-triazin-3-yl2.6-F2H
4425-chloro-6-fluoro-1,2,4-triazin-3-yl2.6-F2H
4435-bromo-6-fluoro-1,2,4-triazin-3-yl2.6-F2H
4445,6-difluoro-1,2,4-triazin-3-yl2.6-F2H
4456-chloro-5-fluoro-1,2,4-triazin-3-yl2.6-F2H
4466-bromo-5-fluoro-1,2,4-triazin-3-yl2.6-F2H
4471,2,4-triazin-6-yl2.6-F2H
4483-fluoro-1,2,4-triazin-6-yl2.6-F2H
4493-chloro-1,2,4-triazin-6-yl2.6-F2H
4503-bromo-1,2,4-triazin-6-yl2.6-F2H
4515-fluoro-1,2,4-triazin-6-yl2.6-F2H
4525-chloro-1,2,4-triazin-6-yl2.6-F2H
4535-bromo-1,2,4-triazin-6-yl2.6-F2H
4543,5-difluoro-1,2,4-triazin-6-yl2.6-F2H
4555-chloro-3-fluoro-1,2,4-triazin-6-yl2.6-F2H
4565-bromo-3-fluoro-1,2,4-triazin-6-yl2.6-F2H
4573-chloro-5-fluoro-1,2,4-triazin-6-yl2.6-F2H
4583-bromo-5-fluoro-1,2,4-triazin-6-yl2.6-F2H
4596-fluoropyridin-3-yl2.5-F2H
4606-chloropyridin-3-yl2.5-F2H
4616-bromopyridin-3-yl2.5-F2H
4625-fluoropyridin-3-yl2.5-F2H
4635-chloropyridin-3-yl2.5-F2H
4645-bromopyridin-3-yl2.5-F2H
4654-fluoropyridin-3-yl2.5-F2H
4664-chloropyridin-3-yl2.5-F2H
4674-bromopyridin-3-yl2.5-F2H
4682-fluoropyridin-3-yl2.5-F2H
4692-chloropyridin-3-yl2.5-F2H
4702-bromopyridin-3-yl2.5-F2H
4712,6-difluoropyridin-3-yl2.5-F2H
4725-chloro-6-fluoropyridin-3-yl2.5-F2H
4735-bromo-6-fluoropyridin-3-yl2.5-F2H
4745,6-difluoropyridin-3-yl2.5-F2H
4756-chloro-5-fluoropyridin-3-yl2.5-F2H
4766-bromo-5-fluoropyridin-3-yl2.5-F2H
4774,5-difluoropyridin-3-yl2.5-F2H
4784-chloro-5-fluoropyridin-3-yl2.5-F2H
4794-bromo-5-fluoropyridin-3-yl2.5-F2H
4805-chloro-4-fluoropyridin-3-yl2.5-F2H
4814,5-dichloropyridin-3-yl2.5-F2H
4824-bromo-5-chloropyridin-3-yl2.5-F2H
4835-bromo-4-fluoropyridin-3-yl2.5-F2H
4845-bromo-4-chloropyridin-3-yl2.5-F2H
4854,5-dibromopyridin-3-yl2.5-F2H
4862,3-difluoropyridin-4-yl2.5-F2H
4873-chloro-2-fluoropyridin-4-yl2.5-F2H
4883-bromo-2-fluoropyridin-4-yl2.5-F2H
4892-fluoropyridin-4-yl2.5-F2H
4902-chloropyridin-4-yl2.5-F2H
4912-bromopyridin-4-yl2.5-F2H
4922,6-difluoropyridin-4-yl2.5-F2H
4932-chloro-6-fluoropyridin-4-yl2.5-F2H
4942-bromo-6-fluoropyridin-4-yl2.5-F2H
4952,3,6-trifluoropyridin-4-yl2.5-F2H
4963-chloro-2,6-difluoropyridin-4-yl2.5-F2H
4973-bromo-2,6-difluoropyridin-4-yl2.5-F2H
4982-chloro-3,6-difluoropyridin-4-yl2.5-F2H
4992-bromo-3,6-difluoropyridin-4-yl2.5-F2H
5006-chloro-2,3-difluoropyridin-4-yl2.5-F2H
5016-bromo-2,3-difluoropyridin-4-yl2.5-F2H
5022,5,6-trifluoropyridin-3-yl2.5-F2H
5032-chloro-5,6-difluoropyridin-3-yl2.5-F2H
5042-bromo-5,6-difluoropyridin-3-yl2.5-F2H
5056-chloro-2,5-difluoropyridin-3-yl2.5-F2H
5066-bromo-2,5-difluoropyridin-3-yl2.5-F2H
5075-chloro-2,6-difluoropyridin-3-yl2.5-F2H
5085-bromo-2,6-difluoropyridin-3-yl2.5-F2H
5096-fluoropyridin-2-yl2.5-F2H
5106-chloropyridin-2-yl2.5-F2H
5116-bromopyridin-2-yl2.5-F2H
5125-fluoropyridin-2-yl2.5-F2H
5135-chloropyridin-2-yl2.5-F2H
5145-bromopyridin-2-yl2.5-F2H
5154-fluoropyridin-2-yl2.5-F2H
5164-chloropyridin-2-yl2.5-F2H
5174-bromopyridin-2-yl2.5-F2H
5183-fluoropyridin-2-yl2.5-F2H
5193-chloropyridin-2-yl2.5-F2H
5203-bromopyridin-2-yl2.5-F2H
5213,4-difluoropyridin-2-yl2.5-F2H
5224-chloro-3-fluoropyridin-2-yl2.5-F2H
5234-bromo-3-fluoropyridin-2-yl2.5-F2H
5243,5-difluoropyridin-2-yl2.5-F2H
5255-chloro-3-fluoropyridin-2-yl2.5-F2H
5265-bromo-3-fluoropyridin-2-yl2.5-F2H
5273,6-difluoropyridin-2-yl2.5-F2H
5286-chloro-3-fluoropyridin-2-yl2.5-F2H
5296-bromo-3-fluoropyridin-2-yl2.5-F2H
5303,4,6-trifluoropyridin-2-yl2.5-F2H
5314-chloro-3,6-difluoropyridin-2-yl2.5-F2H
5324-bromo-3,6-difluoropyridin-2-yl2.5-F2H
5333,5,6-trifluoropyridin-2-yl2.5-F2H
5345-chloro-3,6-difluoropyridin-2-yl2.5-F2H
5355-bromo-3,6-difluoropyridin-2-yl2.5-F2H
5364,5,6-trifluoropyridin-3-yl2.5-F2H
5374-chloro-5,6-difluoropyridin-3-yl2.5-F2H
5384-bromo-5,6-difluoropyridin-3-yl2.5-F2H
5395-chloro-4,6-difluoropyridin-3-yl2.5-F2H
5405-bromo-4,6-difluoropyridin-3-yl2.5-F2H
5416-chloro-4,5-difluoropyridin-3-yl2.5-F2H
5426-bromo-4,5-difluoropyridin-3-yl2.5-F2H
543pyridin-3-yl2.5-F2H
544pyridin-2-yl2.5-F2H
545pyridin-4-yl2.5-F2H
5462-fluoropyrimidin-4-yl2.5-F2H
5472-chloropyrimidin-4-yl2.5-F2H
5482-bromopyrimidin-4-yl2.5-F2H
5492,6-difluoropyrimidin-4-yl2.5-F2H
5506-chloro-2-fluoropyrimidin-4-yl2.5-F2H
5516-bromo-2-fluoropyrimidin-4-yl2.5-F2H
5526-fluoropyrimidin-4-yl2.5-F2H
5536-chloropyrimidin-4-yl2.5-F2H
5546-bromopyrimidin-4-yl2.5-F2H
5554-fluoropyrimidin-2-yl2.5-F2H
5564-chloropyrimidin-2-yl2.5-F2H
5574-bromopyrimidin-2-yl2.5-F2H
5584,5-difluoropyrimidin-2-yl2.5-F2H
5595-chloro-4-fluoropyrimidin-2-yl2.5-F2H
5605-bromo-4-fluoropyrimidin-2-yl2.5-F2H
5614-chloro-5-fluoropyrimidin-2-yl2.5-F2H
5624-bromo-5-fluoropyrimidin-2-yl2.5-F2H
5634,6-difluoropyrimidin-2-yl2.5-F2H
5644-chloro-6-fluoropyrimidin-2-yl2.5-F2H
5654-bromo-6-fluoropyrimidin-2-yl2.5-F2H
566pyrimidin-2-yl2.5-F2H
567pyrimidin-4-yl2.5-F2H
568pyrimidin-5-yl2.5-F2H
5692,4-difluoropyrimidin-5-yl2.5-F2H
5704-chloro-2-fluoropyrimidin-5-yl2.5-F2H
5714-bromo-2-fluoropyrimidin-5-yl2.5-F2H
5722-fluoropyrimidin-5-yl2.5-F2H
5732-chloropyrimidin-5-yl2.5-F2H
5742-bromopyrimidin-5-yl2.5-F2H
575pyridazin-3-yl2.5-F2H
576pyridazin-4-yl2.5-F2H
5776-fluoropyridazin-4-yl2.5-F2H
5786-chloropyridazin-4-yl2.5-F2H
5796-bromopyridazin-4-yl2.5-F2H
5805,6-difluoropyridazin-4-yl2.5-F2H
5815-chloro-6-fluoropyridazin-4-yl2.5-F2H
5825-bromo-6-fluoropyridazin-4-yl2.5-F2H
5836-chloro-5-fluoropyridazin-4-yl2.5-F2H
5846-bromo-5-fluoropyridazin-4-yl2.5-F2H
5853,5-difluoropyridazin-4-yl2.5-F2H
5863-chloro-5-fluoropyridazin-4-yl2.5-F2H
5873-bromo-5-fluoropyridazin-4-yl2.5-F2H
5885-chloro-3-fluoropyridazin-4-yl2.5-F2H
5895-bromo-3-fluoropyridazin-4-yl2.5-F2H
5903,6-difluoropyridazin-4-yl2.5-F2H
5916-chloro-3-fluoropyridazin-4-yl2.5-F2H
5926-bromo-3-fluoropyridazin-4-yl2.5-F2H
5933-chloro-6-fluoropyridazin-4-yl2.5-F2H
5943-bromo-6-fluoropyridazin-4-yl2.5-F2H
5956-fluoropyridazin-3-yl2.5-F2H
5966-chloropyridazin-3-yl2.5-F2H
5976-bromopyridazin-3-yl2.5-F2H
5985-fluoropyridazin-3-yl2.5-F2H
5995-chloropyridazin-3-yl2.5-F2H
6005-bromopyridazin-3-yl2.5-F2H
6014-fluoropyridazin-3-yl2.5-F2H
6024-chloropyridazin-3-yl2.5-F2H
6034-bromopyridazin-3-yl2.5-F2H
6045,6-difluoropyridazin-3-yl2.5-F2H
6055-chloro-6-fluoropyridazin-3-yl2.5-F2H
6065-bromo-6-fluoropyridazin-3-yl2.5-F2H
6076-chloro-5-fluoropyridazin-3-yl2.5-F2H
6086-bromo-5-fluoropyridazin-3-yl2.5-F2H
6094,6-difluoropyridazin-3-yl2.5-F2H
6104-chloro-6-fluoropyridazin-3-yl2.5-F2H
6114-bromo-6-fluoropyridazin-3-yl2.5-F2H
6126-chloro-4-fluoropyridazin-3-yl2.5-F2H
6136-bromo-4-fluoropyridazin-3-yl2.5-F2H
6144,5-difluoropyridazin-3-yl2.5-F2H
6155-chloro-4-fluoropyridazin-3-yl2.5-F2H
6165-bromo-4-fluoropyridazin-3-yl2.5-F2H
6174-chloro-5-fluoropyridazin-3-yl2.5-F2H
6184-bromo-5-fluoropyridazin-3-yl2.5-F2H
619pyrazin-2-yl2.5-F2H
6203-fluoropyrazin-2-yl2.5-F2H
6213-chloropyrazin-2-yl2.5-F2H
6223-bromopyrazin-2-yl2.5-F2H
6236-fluoropyrazin-2-yl2.5-F2H
6246-chloropyrazin-2-yl2.5-F2H
6256-bromopyrazin-2-yl2.5-F2H
6265-fluoropyrazin-2-yl2.5-F2H
6275-chloropyrazin-2-yl2.5-F2H
6285-bromopyrazin-2-yl2.5-F2H
6295,6-difluoropyrazin-2-yl2.5-F2H
6305-chloro-6-fluoropyrazin-2-yl2.5-F2H
6315-bromo-6-fluoropyrazin-2-yl2.5-F2H
6326-chloro-5-fluoropyrazin-2-yl2.5-F2H
6336-bromo-5-fluoropyrazin-2-yl2.5-F2H
6343,5-difluoropyrazin-2-yl2.5-F2H
6353-chloro-5-fluoropyrazin-2-yl2.5-F2H
6363-bromo-5-fluoropyrazin-2-yl2.5-F2H
6375-chloro-3-fluoropyrazin-2-yl2.5-F2H
6385-bromo-3-fluoropyrazin-2-yl2.5-F2H
6393,6-difluoropyrazin-2-yl2.5-F2H
6406-chloro-3-fluoropyrazin-2-yl2.5-F2H
6416-bromo-3-fluoropyrazin-2-yl2.5-F2H
6423-chloro-6-fluoropyrazin-2-yl2.5-F2H
6433-bromo-6-fluoropyrazin-2-yl2.5-F2H
6442-thienyl2.5-F2H
6455-fluoro-2-thienyl2.5-F2H
6465-chloro-2-thienyl2.5-F2H
6475-bromo-2-thienyl2.5-F2H
6484-fluoro-2-thienyl2.5-F2H
6494-chloro-2-thienyl2.5-F2H
6504-bromo-2-thienyl2.5-F2H
6512-fluoro-2-thienyl2.5-F2H
6523-chloro-2-thienyl2.5-F2H
6533-bromo-2-thienyl2.5-F2H
6543-thienyl2.5-F2H
6552-fluoro-3-thienyl2.5-F2H
6562-chloro-3-thienyl2.5-F2H
6572-bromo-3-thienyl2.5-F2H
6585-fluoro-3-thienyl2.5-F2H
6595-chloro-3-thienyl2.5-F2H
6605-bromo-3-thienyl2.5-F2H
6614-fluoro-3-thienyl2.5-F2H
6624-chloro-3-thienyl2.5-F2H
6634-bromo-3-thienyl2.5-F2H
6642,4-difluoro-3-thienyl2.5-F2H
6652-chloro-4-fluoro-3-thienyl2.5-F2H
6662-bromo-4-fluoro-3-thienyl2.5-F2H
6674-chloro-2-fluoro-3-thienyl2.5-F2H
6684-bromo-2-fluoro-3-thienyl2.5-F2H
6692,5-difluoro-3-thienyl2.5-F2H
6705-chloro-2-fluoro-3-thienyl2.5-F2H
6715-bromo-2-fluoro-3-thienyl2.5-F2H
6722-chloro-5-fluoro-3-thienyl2.5-F2H
6732-bromo-5-fluoro-3-thienyl2.5-F2H
6744,5-difluoro-3-thienyl2.5-F2H
6754-chloro-5-fluoro-3-thienyl2.5-F2H
6764-bromo-5-fluoro-3-thienyl2.5-F2H
6775-chloro-4-fluoro-3-thienyl2.5-F2H
6785-bromo-4-fluoro-3-thienyl2.5-F2H
6793,4-difluoro-2-thienyl2.5-F2H
6804-chloro-3-fluoro-2-thienyl2.5-F2H
6814-bromo-3-fluoro-2-thienyl2.5-F2H
6823-chloro-4-fluoro-2-thienyl2.5-F2H
6833-bromo-4-fluoro-2-thienyl2.5-F2H
6843,5-difluoro-2-thienyl2.5-F2H
6855-chloro-3-fluoro-2-thienyl2.5-F2H
6865-bromo-3-fluoro-2-thienyl2.5-F2H
6873-chloro-5-fluoro-2-thienyl2.5-F2H
6883-bromo-5-fluoro-2-thienyl2.5-F2H
6894,5-difluoro-2-thienyl2.5-F2H
6904-chloro-5-fluoro-2-thienyl2.5-F2H
6914-bromo-5-fluoro-2-thienyl2.5-F2H
6925-chloro-4-fluoro-2-thienyl2.5-F2H
6935-bromo-4-fluoro-2-thienyl2.5-F2H
6942-furyl2.5-F2H
6955-fluoro-2-furyl2.5-F2H
6965-chloro-2-furyl2.5-F2H
6975-bromo-2-furyl2.5-F2H
6984-fluoro-2-furyl2.5-F2H
6994-chloro-2-furyl2.5-F2H
7004-bromo-2-furyl2.5-F2H
7012-fluoro-2-furyl2.5-F2H
7023-chloro-2-furyl2.5-F2H
7033-bromo-2-furyl2.5-F2H
7043-furyl2.5-F2H
7052-fluoro-3-furyl2.5-F2H
7062-chloro-3-furyl2.5-F2H
7072-bromo-3-furyl2.5-F2H
7085-fluoro-3-furyl2.5-F2H
7095-chloro-3-furyl2.5-F2H
7105-bromo-3-furyl2.5-F2H
7114-fluoro-3-furyl2.5-F2H
7124-chloro-3-furyl2.5-F2H
7134-bromo-3-furyl2.5-F2H
7142,4-difluoro-3-furyl2.5-F2H
7152-chloro-4-fluoro-3-furyl2.5-F2H
7162-bromo-4-fluoro-3-furyl2.5-F2H
7174-chloro-2-fluoro-3-furyl2.5-F2H
7184-bromo-2-fluoro-3-furyl2.5-F2H
7192,5-difluoro-3-furyl2.5-F2H
7205-chloro-2-fluoro-3-furyl2.5-F2H
7215-bromo-2-fluoro-3-furyl2.5-F2H
7222-chloro-5-fluoro-3-furyl2.5-F2H
7232-bromo-5-fluoro-3-furyl2.5-F2H
7244,5-difluoro-3-furyl2.5-F2H
7254-chloro-5-fluoro-3-furyl2.5-F2H
7264-bromo-5-fluoro-3-furyl2.5-F2H
7275-chloro-4-fluoro-3-furyl2.5-F2H
7285-bromo-4-fluoro-3-furyl2.5-F2H
7293,4-difluoro-2-furyl2.5-F2H
7304-chloro-3-fluoro-2-furyl2.5-F2H
7314-bromo-3-fluoro-2-furyl2.5-F2H
7323-chloro-4-fluoro-2-furyl2.5-F2H
7333-bromo-4-fluoro-2-furyl2.5-F2H
7343,5-difluoro-2-furyl2.5-F2H
7355-chloro-3-fluoro-2-furyl2.5-F2H
7365-bromo-3-fluoro-2-furyl2.5-F2H
7373-chloro-5-fluoro-2-furyl2.5-F2H
7383-bromo-5-fluoro-2-furyl2.5-F2H
7394,5-difluoro-2-furyl2.5-F2H
7404-chloro-5-fluoro-2-furyl2.5-F2H
7414-bromo-5-fluoro-2-furyl2.5-F2H
7425-chloro-4-fluoro-2-furyl2.5-F2H
7435-bromo-4-fluoro-2-furyl2.5-F2H
7441,3-oxazol-2-yl2.5-F2H
7451,3-oxazol-5-yl2.5-F2H
7461,3-oxazol-4-yl2.5-F2H
7472-fluoro-1,3-oxazol-4-yl2.5-F2H
7482-chloro-1,3-oxazol-4-yl2.5-F2H
7492-bromo-1,3-oxazol-4-yl2.5-F2H
7502,5-difluoro-1,3-oxazol-4-yl2.5-F2H
7515-chloro-2-fluoro-1,3-oxazol-4-yl2.5-F2H
7525-bromo-2-fluoro-1,3-oxazol-4-yl2.5-F2H
7532-chloro-5-fluoro-1,3-oxazol-4-yl2.5-F2H
7542-bromo-5-fluoro-1,3-oxazol-4-yl2.5-F2H
7555-fluoro-1,3-oxazol-2-yl2.5-F2H
7565-chloro-1,3-oxazol-2-yl2.5-F2H
7575-bromo-1,3-oxazol-2-yl2.5-F2H
7584,5-difluoro-1,3-oxazol-2-yl2.5-F2H
7594-chloro-5-fluoro-1,3-oxazol-2-yl2.5-F2H
7604-bromo-5-fluoro-1,3-oxazol-2-yl2.5-F2H
7615-chloro-4-fluoro-1,3-oxazol-2-yl2.5-F2H
7625-bromo-4-fluoro-1,3-oxazol-2-yl2.5-F2H
7632-fluoro-1,3-oxazol-5-yl2.5-F2H
7642-chloro-1,3-oxazol-5-yl2.5-F2H
7652-bromo-1,3-oxazol-5-yl2.5-F2H
7662,4-difluoro-1,3-oxazol-5-yl2.5-F2H
7674-chloro-2-fluoro-1,3-oxazol-5-yl2.5-F2H
7684-bromo-2-fluoro-1,3-oxazol-5-yl2.5-F2H
7692-chloro-4-fluoro-1,3-oxazol-5-yl2.5-F2H
7702-bromo-4-fluoro-1,3-oxazol-5-yl2.5-F2H
7711,3-thiazol-2-yl2.5-F2H
7721,3-thiazol-5-yl2.5-F2H
7731,3-thiazol-4-yl2.5-F2H
7742-fluoro-1,3-thiazol-4-yl2.5-F2H
7752-chloro-1,3-thiazol-4-yl2.5-F2H
7762-bromo-1,3-thiazol-4-yl2.5-F2H
7772,5-difluoro-1,3-thiazol-4-yl2.5-F2H
7785-chloro-2-fluoro-1,3-thiazol-4-yl2.5-F2H
7795-bromo-2-fluoro-1,3-thiazol-4-yl2.5-F2H
7802-chloro-5-fluoro-1,3-thiazol-4-yl2.5-F2H
7812-bromo-5-fluoro-1,3-thiazol-4-yl2.5-F2H
7825-fluoro-1,3-thiazol-2-yl2.5-F2H
7835-chloro-1,3-thiazol-2-yl2.5-F2H
7845-bromo-1,3-thiazol-2-yl2.5-F2H
7854,5-difluoro-1,3-thiazol-2-yl2.5-F2H
7864-chloro-5-fluoro-1,3-thiazol-2-yl2.5-F2H
7874-bromo-5-fluoro-1,3-thiazol-2-yl2.5-F2H
7885-chloro-4-fluoro-1,3-thiazol-2-yl2.5-F2H
7895-bromo-4-fluoro-1,3-thiazol-2-yl2.5-F2H
7902-fluoro-1,3-thiazol-5-yl2.5-F2H
7912-chloro-1,3-thiazol-5-yl2.5-F2H
7922-bromo-1,3-thiazol-5-yl2.5-F2H
7932,4-difluoro-1,3-thiazol-5-yl2.5-F2H
7944-chloro-2-fluoro-1,3-thiazol-5-yl2.5-F2H
7954-bromo-2-fluoro-1,3-thiazol-5-yl2.5-F2H
7962-chloro-4-fluoro-1,3-thiazol-5-yl2.5-F2H
7972-bromo-4-fluoro-1,3-thiazol-5-yl2.5-F2H
7981-methyl-1H-imidazol-2-yl2.5-F2H
7991-methyl-1H-imidazol-5-yl2.5-F2H
8001-methyl-1H-imidazol-4-yl2.5-F2H
8012-fluoro-1,3-1-methyl-1H-imidazol-4-yl2.5-F2H
8022-chloro-1,3-1-methyl-1H-imidazol-4-yl2.5-F2H
8032-bromo-1,3-1-methyl-1H-imidazol-4-yl2.5-F2H
8042,5-difluoro-1,3-1-methyl-1H-imidazol-4-yl2.5-F2H
8055-chloro-2-fluoro-1,3-1-methyl-1H-imidazol-4-2.5-F2H
yl
8065-bromo-2-fluoro-1,3-1-methyl-1H-imidazol-4-2.5-F2H
yl
8072-chloro-5-fluoro-1,3-1-methyl-1H-imidazol-4-2.5-F2H
yl
8082-bromo-5-fluoro-1,3-1-methyl-1H-imidazol-4-2.5-F2H
yl
8095-fluoro-1,3-1-methyl-1H-imidazol-2-yl2.5-F2H
8105-chloro-1,3-1-methyl-1H-imidazol-2-yl2.5-F2H
8115-bromo-1,3-1-methyl-1H-imidazol-2-yl2.5-F2H
8124,5-difluoro-1,3-1-methyl-1H-imidazol-2-yl2.5-F2H
8134-chloro-5-fluoro-1,3-1-methyl-1H-imidazol-2-2.5-F2H
yl
8144-bromo-5-fluoro-1,3-1-methyl-1H-imidazol-2-2.5-F2H
yl
8155-chloro-4-fluoro-1,3-1-methyl-1H-imidazol-2-2.5-F2H
yl
8165-bromo-4-fluoro-1,3-1-methyl-1H-imidazol-2-2.5-F2H
yl
8172-fluoro-1,3-1-methyl-1H-imidazol-5-yl2.5-F2H
8182-chloro-1,3-1-methyl-1H-imidazol-5-yl2.5-F2H
8192-bromo-1,3-1-methyl-1H-imidazol-5-yl2.5-F2H
8202,4-difluoro-1,3-1-methyl-1H-imidazol-5-yl2.5-F2H
8214-chloro-2-fluoro-1,3-1-methyl-1H-imidazol-5-2.5-F2H
yl
8224-bromo-2-fluoro-1,3-1-methyl-1H-imidazol-5-2.5-F2H
yl
8232-chloro-4-fluoro-1,3-1-methyl-1H-imidazol-5-2.5-F2H
yl
8242-bromo-4-fluoro-1,3-1-methyl-1H-imidazol-5-2.5-F2H
yl
8251-methyl-1H-pyrazol-5-yl2.5-F2H
8263-fluoro-1-methyl-1H-pyrazol-5-yl2.5-F2H
8273-chloro-1-methyl-1H-pyrazol-5-yl2.5-F2H
8283-bromo-1-methyl-1H-pyrazol-5-yl2.5-F2H
8294-fluoro-1-methyl-1H-pyrazol-5-yl2.5-F2H
8304-chloro-1-methyl-1H-pyrazol-5-yl2.5-F2H
8314-bromo-1-methyl-1H-pyrazol-5-yl2.5-F2H
8323,4-difluoro-1-methyl-1H-pyrazol-5-yl2.5-F2H
8334-chloro-3-fluoro-1-methyl-1H-pyrazol-5-yl2.5-F2H
8344-bromo-3-fluoro-1-methyl-1H-pyrazol-5-yl2.5-F2H
8353-chloro-4-fluoro-1-methyl-1H-pyrazol-5-yl2.5-F2H
8363-bromo-4-fluoro-1-methyl-1H-pyrazol-5-yl2.5-F2H
8371-methyl-1H-pyrazol-4-yl2.5-F2H
8385-fluoro-1-methyl-1H-pyrazol-4-yl2.5-F2H
8395-chloro-1-methyl-1H-pyrazol-4-yl2.5-F2H
8405-bromo-1-methyl-1H-pyrazol-4-yl2.5-F2H
8413-fluoro-1-methyl-1H-pyrazol-4-yl2.5-F2H
8423-chloro-1-methyl-1H-pyrazol-4-yl2.5-F2H
8433-bromo-1-methyl-1H-pyrazol-4-yl2.5-F2H
8443,5-difluoro-1-methyl-1H-pyrazol-4-yl2.5-F2H
8455-chloro-3-fluoro-1-methyl-1H-pyrazol-4-yl2.5-F2H
8465-bromo-3-fluoro-1-methyl-1H-pyrazol-4-yl2.5-F2H
8473-chloro-5-fluoro-1-methyl-1H-pyrazol-4-yl2.5-F2H
8483-bromo-5-fluoro-1-methyl-1H-pyrazol-4-yl2.5-F2H
8495-fluoro-1-methyl-1H-pyrazol-3-yl2.5-F2H
8505-chloro-1-methyl-1H-pyrazol-3-yl2.5-F2H
8515-bromo-1-methyl-1H-pyrazol-3-yl2.5-F2H
8524-fluoro-1-methyl-1H-pyrazol-3-yl2.5-F2H
8534-chloro-1-methyl-1H-pyrazol-3-yl2.5-F2H
8544-bromo-1-methyl-1H-pyrazol-3-yl2.5-F2H
8554,5-difluoro-1-methyl-1H-pyrazol-3-yl2.5-F2H
8564-chloro-5-fluoro-1-methyl-1H-pyrazol-3-yl2.5-F2H
8574-bromo-5-fluoro-1-methyl-1H-pyrazol-3-yl2.5-F2H
8585-chloro-4-fluoro-1-methyl-1H-pyrazol-3-yl2.5-F2H
8595-bromo-4-fluoro-1-methyl-1H-pyrazol-3-yl2.5-F2H
8601,3,5-triazin-2-yl2.5-F2H
8614-fluoro-1,3,5-triazin-2-yl2.5-F2H
8624-chloro-1,3,5-triazin-2-yl2.5-F2H
8634-bromo-1,3,5-triazin-2-yl2.5-F2H
8644,6-difluoro-1,3,5-triazin-2-yl2.5-F2H
8654-chloro-6-fluoro-1,3,5-triazin-2-yl2.5-F2H
8664-bromo-6-fluoro-1,3,5-triazin-2-yl2.5-F2H
8671,2,3-triazin-4-yl2.5-F2H
8686-fluoro-1,2,3-triazin-4-yl2.5-F2H
8696-chloro-1,2,3-triazin-4-yl2.5-F2H
8706-bromo-1,2,3-triazin-4-yl2.5-F2H
8715,6-difluoro-1,2,3-triazin-4-yl2.5-F2H
8725-chloro-6-fluoro-1,2,3-triazin-4-yl2.5-F2H
8735-bromo-6-fluoro-1,2,3-triazin-4-yl2.5-F2H
8741,2,3-triazin-5-yl2.5-F2H
8754-fluoro-1,2,3-triazin-5-yl2.5-F2H
8764-chloro-1,2,3-triazin-5-yl2.5-F2H
8774-bromo-1,2,3-triazin-5-yl2.5-F2H
8784,6-difluoro-1,2,3-triazin-5-yl2.5-F2H
8794-chloro-6-fluoro-1,2,3-triazin-5-yl2.5-F2H
8804-bromo-6-fluoro-1,2,3-triazin-5-yl2.5-F2H
8811,2,4-triazin-5-yl2.5-F2H
8823-fluoro-1,2,4-triazin-5-yl2.5-F2H
8833-chloro-1,2,4-triazin-5-yl2.5-F2H
8843-bromo-1,2,4-triazin-5-yl2.5-F2H
8856-fluoro-1,2,4-triazin-5-yl2.5-F2H
8866-chloro-1,2,4-triazin-5-yl2.5-F2H
8876-bromo-1,2,4-triazin-5-yl2.5-F2H
8883,6-difluoro-1,2,4-triazin-5-yl2.5-F2H
8896-chloro-3-fluoro-1,2,4-triazin-5-yl2.5-F2H
8906-bromo-3-fluoro-1,2,4-triazin-5-yl2.5-F2H
8913-chloro-6-fluoro-1,2,4-triazin-5-yl2.5-F2H
8923-bromo-6-fluoro-1,2,4-triazin-5-yl2.5-F2H
8931,2,4-triazin-3-yl2.5-F2H
8946-fluoro-1,2,4-triazin-3-yl2.5-F2H
8956-chloro-1,2,4-triazin-3-yl2.5-F2H
8966-bromo-1,2,4-triazin-3-yl2.5-F2H
8975-fluoro-1,2,4-triazin-3-yl2.5-F2H
8985-chloro-1,2,4-triazin-3-yl2.5-F2H
8995-bromo-1,2,4-triazin-3-yl2.5-F2H
9005-chloro-6-fluoro-1,2,4-triazin-3-yl2.5-F2H
9015-bromo-6-fluoro-1,2,4-triazin-3-yl2.5-F2H
9025,6-difluoro-1,2,4-triazin-3-yl2.5-F2H
9036-chloro-5-fluoro-1,2,4-triazin-3-yl2.5-F2H
9046-bromo-5-fluoro-1,2,4-triazin-3-yl2.5-F2H
9051,2,4-triazin-6-yl2.5-F2H
9063-fluoro-1,2,4-triazin-6-yl2.5-F2H
9073-chloro-1,2,4-triazin-6-yl2.5-F2H
9083-bromo-1,2,4-triazin-6-yl2.5-F2H
9095-fluoro-1,2,4-triazin-6-yl2.5-F2H
9105-chloro-1,2,4-triazin-6-yl2.5-F2H
9115-bromo-1,2,4-triazin-6-yl2.5-F2H
9123,5-difluoro-1,2,4-triazin-6-yl2.5-F2H
9135-chloro-3-fluoro-1,2,4-triazin-6-yl2.5-F2H
9145-bromo-3-fluoro-1,2,4-triazin-6-yl2.5-F2H
9153-chloro-5-fluoro-1,2,4-triazin-6-yl2.5-F2H
9163-bromo-5-fluoro-1,2,4-triazin-6-yl2.5-F2H
9176-fluoropyridin-3-yl2.6-F2C(O)Me
9186-chloropyridin-3-yl2.6-F2C(O)Me
9196-bromopyridin-3-yl2.6-F2C(O)Me
9205-fluoropyridin-3-yl2.6-F2C(O)Me
9215-chloropyridin-3-yl2.6-F2C(O)Me
9225-bromopyridin-3-yl2.6-F2C(O)Me
9234-fluoropyridin-3-yl2.6-F2C(O)Me
9244-chloropyridin-3-yl2.6-F2C(O)Me
9254-bromopyridin-3-yl2.6-F2C(O)Me
9262-fluoropyridin-3-yl2.6-F2C(O)Me
9272-chloropyridin-3-yl2.6-F2C(O)Me
9282-bromopyridin-3-yl2.6-F2C(O)Me
9292,6-difluoropyridin-3-yl2.6-F2C(O)Me
9305-chloro-6-fluoropyridin-3-yl2.6-F2C(O)Me
9315-bromo-6-fluoropyridin-3-yl2.6-F2C(O)Me
9325,6-difluoropyridin-3-yl2.6-F2C(O)Me
9336-chloro-5-fluoropyridin-3-yl2.6-F2C(O)Me
9346-bromo-5-fluoropyridin-3-yl2.6-F2C(O)Me
9354,5-difluoropyridin-3-yl2.6-F2C(O)Me
9364-chloro-5-fluoropyridin-3-yl2.6-F2C(O)Me
9374-bromo-5-fluoropyridin-3-yl2.6-F2C(O)Me
9385-chloro-4-fluoropyridin-3-yl2.6-F2C(O)Me
9394,5-dichloropyridin-3-yl2.6-F2C(O)Me
9404-bromo-5-chloropyridin-3-yl2.6-F2C(O)Me
9415-bromo-4-fluoropyridin-3-yl2.6-F2C(O)Me
9425-bromo-4-chloropyridin-3-yl2.6-F2C(O)Me
9434,5-dibromopyridin-3-yl2.6-F2C(O)Me
9442,3-difluoropyridin-4-yl2.6-F2C(O)Me
9453-chloro-2-fluoropyridin-4-yl2.6-F2C(O)Me
9463-bromo-2-fluoropyridin-4-yl2.6-F2C(O)Me
9472-fluoropyridin-4-yl2.6-F2C(O)Me
9482-chloropyridin-4-yl2.6-F2C(O)Me
9492-bromopyridin-4-yl2.6-F2C(O)Me
9502,6-difluoropyridin-4-yl2.6-F2C(O)Me
9512-chloro-6-fluoropyridin-4-yl2.6-F2C(O)Me
9522-bromo-6-fluoropyridin-4-yl2.6-F2C(O)Me
9532,3,6-trifluoropyridin-4-yl2.6-F2C(O)Me
9543-chloro-2,6-difluoropyridin-4-yl2.6-F2C(O)Me
9553-bromo-2,6-difluoropyridin-4-yl2.6-F2C(O)Me
9562-chloro-3,6-difluoropyridin-4-yl2.6-F2C(O)Me
9572-bromo-3,6-difluoropyridin-4-yl2.6-F2C(O)Me
9586-chloro-2,3-difluoropyridin-4-yl2.6-F2C(O)Me
9596-bromo-2,3-difluoropyridin-4-yl2.6-F2C(O)Me
9602,5,6-trifluoropyridin-3-yl2.6-F2C(O)Me
9612-chloro-5,6-difluoropyridin-3-yl2.6-F2C(O)Me
9622-bromo-5,6-difluoropyridin-3-yl2.6-F2C(O)Me
9636-chloro-2,5-difluoropyridin-3-yl2.6-F2C(O)Me
9646-bromo-2,5-difluoropyridin-3-yl2.6-F2C(O)Me
9655-chloro-2,6-difluoropyridin-3-yl2.6-F2C(O)Me
9665-bromo-2,6-difluoropyridin-3-yl2.6-F2C(O)Me
9676-fluoropyridin-2-yl2.6-F2C(O)Me
9686-chloropyridin-2-yl2.6-F2C(O)Me
9696-bromopyridin-2-yl2.6-F2C(O)Me
9705-fluoropyridin-2-yl2.6-F2C(O)Me
9715-chloropyridin-2-yl2.6-F2C(O)Me
9725-bromopyridin-2-yl2.6-F2C(O)Me
9734-fluoropyridin-2-yl2.6-F2C(O)Me
9744-chloropyridin-2-yl2.6-F2C(O)Me
9754-bromopyridin-2-yl2.6-F2C(O)Me
9763-fluoropyridin-2-yl2.6-F2C(O)Me
9773-chloropyridin-2-yl2.6-F2C(O)Me
9783-bromopyridin-2-yl2.6-F2C(O)Me
9793,4-difluoropyridin-2-yl2.6-F2C(O)Me
9804-chloro-3-fluoropyridin-2-yl2.6-F2C(O)Me
9814-bromo-3-fluoropyridin-2-yl2.6-F2C(O)Me
9823,5-difluoropyridin-2-yl2.6-F2C(O)Me
9835-chloro-3-fluoropyridin-2-yl2.6-F2C(O)Me
9845-bromo-3-fluoropyridin-2-yl2.6-F2C(O)Me
9853,6-difluoropyridin-2-yl2.6-F2C(O)Me
9866-chloro-3-fluoropyridin-2-yl2.6-F2C(O)Me
9876-bromo-3-fluoropyridin-2-yl2.6-F2C(O)Me
9883,4,6-trifluoropyridin-2-yl2.6-F2C(O)Me
9894-chloro-3,6-difluoropyridin-2-yl2.6-F2C(O)Me
9904-bromo-3,6-difluoropyridin-2-yl2.6-F2C(O)Me
9913,5,6-trifluoropyridin-2-yl2.6-F2C(O)Me
9925-chloro-3,6-difluoropyridin-2-yl2.6-F2C(O)Me
9935-bromo-3,6-difluoropyridin-2-yl2.6-F2C(O)Me
9944,5,6-trifluoropyridin-3-yl2.6-F2C(O)Me
9954-chloro-5,6-difluoropyridin-3-yl2.6-F2C(O)Me
9964-bromo-5,6-difluoropyridin-3-yl2.6-F2C(O)Me
9975-chloro-4,6-difluoropyridin-3-yl2.6-F2C(O)Me
9985-bromo-4,6-difluoropyridin-3-yl2.6-F2C(O)Me
9996-chloro-4,5-difluoropyridin-3-yl2.6-F2C(O)Me
10006-bromo-4,5-difluoropyridin-3-yl2.6-F2C(O)Me
1001pyridin-3-yl2.6-F2C(O)Me
1002pyridin-2-yl2.6-F2C(O)Me
1003pyridin-4-yl2.6-F2C(O)Me
10042-fluoropyrimidin-4-yl2.6-F2C(O)Me
10052-chloropyrimidin-4-yl2.6-F2C(O)Me
10062-bromopyrimidin-4-yl2.6-F2C(O)Me
10072,6-difluoropyrimidin-4-yl2.6-F2C(O)Me
10086-chloro-2-fluoropyrimidin-4-yl2.6-F2C(O)Me
10096-bromo-2-fluoropyrimidin-4-yl2.6-F2C(O)Me
10106-fluoropyrimidin-4-yl2.6-F2C(O)Me
10116-chloropyrimidin-4-yl2.6-F2C(O)Me
10126-bromopyrimidin-4-yl2.6-F2C(O)Me
10134-fluoropyrimidin-2-yl2.6-F2C(O)Me
10144-chloropyrimidin-2-yl2.6-F2C(O)Me
10154-bromopyrimidin-2-yl2.6-F2C(O)Me
10164,5-difluoropyrimidin-2-yl2.6-F2C(O)Me
10175-chloro-4-fluoropyrimidin-2-yl2.6-F2C(O)Me
10185-bromo-4-fluoropyrimidin-2-yl2.6-F2C(O)Me
10194-chloro-5-fluoropyrimidin-2-yl2.6-F2C(O)Me
10204-bromo-5-fluoropyrimidin-2-yl2.6-F2C(O)Me
10214,6-difluoropyrimidin-2-yl2.6-F2C(O)Me
10224-chloro-6-fluoropyrimidin-2-yl2.6-F2C(O)Me
10234-bromo-6-fluoropyrimidin-2-yl2.6-F2C(O)Me
1024pyrimidin-2-yl2.6-F2C(O)Me
1025pyrimidin-4-yl2.6-F2C(O)Me
1026pyrimidin-5-yl2.6-F2C(O)Me
10272,4-difluoropyrimidin-5-yl2.6-F2C(O)Me
10284-chloro-2-fluoropyrimidin-5-yl2.6-F2C(O)Me
10294-bromo-2-fluoropyrimidin-5-yl2.6-F2C(O)Me
10302-fluoropyrimidin-5-yl2.6-F2C(O)Me
10312-chloropyrimidin-5-yl2.6-F2C(O)Me
10322-bromopyrimidin-5-yl2.6-F2C(O)Me
1033pyridazin-3-yl2.6-F2C(O)Me
1034pyridazin-4-yl2.6-F2C(O)Me
10356-fluoropyridazin-4-yl2.6-F2C(O)Me
10366-chloropyridazin-4-yl2.6-F2C(O)Me
10376-bromopyridazin-4-yl2.6-F2C(O)Me
10385,6-difluoropyridazin-4-yl2.6-F2C(O)Me
10395-chloro-6-fluoropyridazin-4-yl2.6-F2C(O)Me
10405-bromo-6-fluoropyridazin-4-yl2.6-F2C(O)Me
10416-chloro-5-fluoropyridazin-4-yl2.6-F2C(O)Me
10426-bromo-5-fluoropyridazin-4-yl2.6-F2C(O)Me
10433,5-difluoropyridazin-4-yl2.6-F2C(O)Me
10443-chloro-5-fluoropyridazin-4-yl2.6-F2C(O)Me
10453-bromo-5-fluoropyridazin-4-yl2.6-F2C(O)Me
10465-chloro-3-fluoropyridazin-4-yl2.6-F2C(O)Me
10475-bromo-3-fluoropyridazin-4-yl2.6-F2C(O)Me
10483,6-difluoropyridazin-4-yl2.6-F2C(O)Me
10496-chloro-3-fluoropyridazin-4-yl2.6-F2C(O)Me
10506-bromo-3-fluoropyridazin-4-yl2.6-F2C(O)Me
10513-chloro-6-fluoropyridazin-4-yl2.6-F2C(O)Me
10523-bromo-6-fluoropyridazin-4-yl2.6-F2C(O)Me
10536-fluoropyridazin-3-yl2.6-F2C(O)Me
10546-chloropyridazin-3-yl2.6-F2C(O)Me
10556-bromopyridazin-3-yl2.6-F2C(O)Me
10565-fluoropyridazin-3-yl2.6-F2C(O)Me
10575-chloropyridazin-3-yl2.6-F2C(O)Me
10585-bromopyridazin-3-yl2.6-F2C(O)Me
10594-fluoropyridazin-3-yl2.6-F2C(O)Me
10604-chloropyridazin-3-yl2.6-F2C(O)Me
10614-bromopyridazin-3-yl2.6-F2C(O)Me
10625,6-difluoropyridazin-3-yl2.6-F2C(O)Me
10635-chloro-6-fluoropyridazin-3-yl2.6-F2C(O)Me
10645-bromo-6-fluoropyridazin-3-yl2.6-F2C(O)Me
10656-chloro-5-fluoropyridazin-3-yl2.6-F2C(O)Me
10666-bromo-5-fluoropyridazin-3-yl2.6-F2C(O)Me
10674,6-difluoropyridazin-3-yl2.6-F2C(O)Me
10684-chloro-6-fluoropyridazin-3-yl2.6-F2C(O)Me
10694-bromo-6-fluoropyridazin-3-yl2.6-F2C(O)Me
10706-chloro-4-fluoropyridazin-3-yl2.6-F2C(O)Me
10716-bromo-4-fluoropyridazin-3-yl2.6-F2C(O)Me
10724,5-difluoropyridazin-3-yl2.6-F2C(O)Me
10735-chloro-4-fluoropyridazin-3-yl2.6-F2C(O)Me
10745-bromo-4-fluoropyridazin-3-yl2.6-F2C(O)Me
10754-chloro-5-fluoropyridazin-3-yl2.6-F2C(O)Me
10764-bromo-5-fluoropyridazin-3-yl2.6-F2C(O)Me
1077pyrazin-2-yl2.6-F2C(O)Me
10783-fluoropyrazin-2-yl2.6-F2C(O)Me
10793-chloropyrazin-2-yl2.6-F2C(O)Me
10803-bromopyrazin-2-yl2.6-F2C(O)Me
10816-fluoropyrazin-2-yl2.6-F2C(O)Me
10826-chloropyrazin-2-yl2.6-F2C(O)Me
10836-bromopyrazin-2-yl2.6-F2C(O)Me
10845-fluoropyrazin-2-yl2.6-F2C(O)Me
10855-chloropyrazin-2-yl2.6-F2C(O)Me
10865-bromopyrazin-2-yl2.6-F2C(O)Me
10875,6-difluoropyrazin-2-yl2.6-F2C(O)Me
10885-chloro-6-fluoropyrazin-2-yl2.6-F2C(O)Me
10895-bromo-6-fluoropyrazin-2-yl2.6-F2C(O)Me
10906-chloro-5-fluoropyrazin-2-yl2.6-F2C(O)Me
10916-bromo-5-fluoropyrazin-2-yl2.6-F2C(O)Me
10923,5-difluoropyrazin-2-yl2.6-F2C(O)Me
10933-chloro-5-fluoropyrazin-2-yl2.6-F2C(O)Me
10943-bromo-5-fluoropyrazin-2-yl2.6-F2C(O)Me
10955-chloro-3-fluoropyrazin-2-yl2.6-F2C(O)Me
10965-bromo-3-fluoropyrazin-2-yl2.6-F2C(O)Me
10973,6-difluoropyrazin-2-yl2.6-F2C(O)Me
10986-chloro-3-fluoropyrazin-2-yl2.6-F2C(O)Me
10996-bromo-3-fluoropyrazin-2-yl2.6-F2C(O)Me
11003-chloro-6-fluoropyrazin-2-yl2.6-F2C(O)Me
11013-bromo-6-fluoropyrazin-2-yl2.6-F2C(O)Me
11022-thienyl2.6-F2C(O)Me
11035-fluoro-2-thienyl2.6-F2C(O)Me
11045-chloro-2-thienyl2.6-F2C(O)Me
11055-bromo-2-thienyl2.6-F2C(O)Me
11064-fluoro-2-thienyl2.6-F2C(O)Me
11074-chloro-2-thienyl2.6-F2C(O)Me
11084-bromo-2-thienyl2.6-F2C(O)Me
11092-fluoro-2-thienyl2.6-F2C(O)Me
11103-chloro-2-thienyl2.6-F2C(O)Me
11113-bromo-2-thienyl2.6-F2C(O)Me
11123-thienyl2.6-F2C(O)Me
11132-fluoro-3-thienyl2.6-F2C(O)Me
11142-chloro-3-thienyl2.6-F2C(O)Me
11152-bromo-3-thienyl2.6-F2C(O)Me
11165-fluoro-3-thienyl2.6-F2C(O)Me
11175-chloro-3-thienyl2.6-F2C(O)Me
11185-bromo-3-thienyl2.6-F2C(O)Me
11194-fluoro-3-thienyl2.6-F2C(O)Me
11204-chloro-3-thienyl2.6-F2C(O)Me
11214-bromo-3-thienyl2.6-F2C(O)Me
11222,4-difluoro-3-thienyl2.6-F2C(O)Me
11232-chloro-4-fluoro-3-thienyl2.6-F2C(O)Me
11242-bromo-4-fluoro-3-thienyl2.6-F2C(O)Me
11254-chloro-2-fluoro-3-thienyl2.6-F2C(O)Me
11264-bromo-2-fluoro-3-thienyl2.6-F2C(O)Me
11272,5-difluoro-3-thienyl2.6-F2C(O)Me
11285-chloro-2-fluoro-3-thienyl2.6-F2C(O)Me
11295-bromo-2-fluoro-3-thienyl2.6-F2C(O)Me
11302-chloro-5-fluoro-3-thienyl2.6-F2C(O)Me
11312-bromo-5-fluoro-3-thienyl2.6-F2C(O)Me
11324,5-difluoro-3-thienyl2.6-F2C(O)Me
11334-chloro-5-fluoro-3-thienyl2.6-F2C(O)Me
11344-bromo-5-fluoro-3-thienyl2.6-F2C(O)Me
11355-chloro-4-fluoro-3-thienyl2.6-F2C(O)Me
11365-bromo-4-fluoro-3-thienyl2.6-F2C(O)Me
11373,4-difluoro-2-thienyl2.6-F2C(O)Me
11384-chloro-3-fluoro-2-thienyl2.6-F2C(O)Me
11394-bromo-3-fluoro-2-thienyl2.6-F2C(O)Me
11403-chloro-4-fluoro-2-thienyl2.6-F2C(O)Me
11413-bromo-4-fluoro-2-thienyl2.6-F2C(O)Me
11423,5-difluoro-2-thienyl2.6-F2C(O)Me
11435-chloro-3-fluoro-2-thienyl2.6-F2C(O)Me
11445-bromo-3-fluoro-2-thienyl2.6-F2C(O)Me
11453-chloro-5-fluoro-2-thienyl2.6-F2C(O)Me
11463-bromo-5-fluoro-2-thienyl2.6-F2C(O)Me
11474,5-difluoro-2-thienyl2.6-F2C(O)Me
11484-chloro-5-fluoro-2-thienyl2.6-F2C(O)Me
11494-bromo-5-fluoro-2-thienyl2.6-F2C(O)Me
11505-chloro-4-fluoro-2-thienyl2.6-F2C(O)Me
11515-bromo-4-fluoro-2-thienyl2.6-F2C(O)Me
11522-furyl2.6-F2C(O)Me
11535-fluoro-2-furyl2.6-F2C(O)Me
11545-chloro-2-furyl2.6-F2C(O)Me
11555-bromo-2-furyl2.6-F2C(O)Me
11564-fluoro-2-furyl2.6-F2C(O)Me
11574-chloro-2-furyl2.6-F2C(O)Me
11584-bromo-2-furyl2.6-F2C(O)Me
11592-fluoro-2-furyl2.6-F2C(O)Me
11603-chloro-2-furyl2.6-F2C(O)Me
11613-bromo-2-furyl2.6-F2C(O)Me
11623-furyl2.6-F2C(O)Me
11632-fluoro-3-furyl2.6-F2C(O)Me
11642-chloro-3-furyl2.6-F2C(O)Me
11652-bromo-3-furyl2.6-F2C(O)Me
11665-fluoro-3-furyl2.6-F2C(O)Me
11675-chloro-3-furyl2.6-F2C(O)Me
11685-bromo-3-furyl2.6-F2C(O)Me
11694-fluoro-3-furyl2.6-F2C(O)Me
11704-chloro-3-furyl2.6-F2C(O)Me
11714-bromo-3-furyl2.6-F2C(O)Me
11722,4-difluoro-3-furyl2.6-F2C(O)Me
11732-chloro-4-fluoro-3-furyl2.6-F2C(O)Me
11742-bromo-4-fluoro-3-furyl2.6-F2C(O)Me
11754-chloro-2-fluoro-3-furyl2.6-F2C(O)Me
11764-bromo-2-fluoro-3-furyl2.6-F2C(O)Me
11772,5-difluoro-3-furyl2.6-F2C(O)Me
11785-chloro-2-fluoro-3-furyl2.6-F2C(O)Me
11795-bromo-2-fluoro-3-furyl2.6-F2C(O)Me
11802-chloro-5-fluoro-3-furyl2.6-F2C(O)Me
11812-bromo-5-fluoro-3-furyl2.6-F2C(O)Me
11824,5-difluoro-3-furyl2.6-F2C(O)Me
11834-chloro-5-fluoro-3-furyl2.6-F2C(O)Me
11844-bromo-5-fluoro-3-furyl2.6-F2C(O)Me
11855-chloro-4-fluoro-3-furyl2.6-F2C(O)Me
11865-bromo-4-fluoro-3-furyl2.6-F2C(O)Me
11873,4-difluoro-2-furyl2.6-F2C(O)Me
11884-chloro-3-fluoro-2-furyl2.6-F2C(O)Me
11894-bromo-3-fluoro-2-furyl2.6-F2C(O)Me
11903-chloro-4-fluoro-2-furyl2.6-F2C(O)Me
11913-bromo-4-fluoro-2-furyl2.6-F2C(O)Me
11923,5-difluoro-2-furyl2.6-F2C(O)Me
11935-chloro-3-fluoro-2-furyl2.6-F2C(O)Me
11945-bromo-3-fluoro-2-furyl2.6-F2C(O)Me
11953-chloro-5-fluoro-2-furyl2.6-F2C(O)Me
11963-bromo-5-fluoro-2-furyl2.6-F2C(O)Me
11974,5-difluoro-2-furyl2.6-F2C(O)Me
11984-chloro-5-fluoro-2-furyl2.6-F2C(O)Me
11994-bromo-5-fluoro-2-furyl2.6-F2C(O)Me
12005-chloro-4-fluoro-2-furyl2.6-F2C(O)Me
12015-bromo-4-fluoro-2-furyl2.6-F2C(O)Me
12021,3-oxazol-2-yl2.6-F2C(O)Me
12031,3-oxazol-5-yl2.6-F2C(O)Me
12041,3-oxazol-4-yl2.6-F2C(O)Me
12052-fluoro-1,3-oxazol-4-yl2.6-F2C(O)Me
12062-chloro-1,3-oxazol-4-yl2.6-F2C(O)Me
12072-bromo-1,3-oxazol-4-yl2.6-F2C(O)Me
12082,5-difluoro-1,3-oxazol-4-yl2.6-F2C(O)Me
12095-chloro-2-fluoro-1,3-oxazol-4-yl2.6-F2C(O)Me
12105-bromo-2-fluoro-1,3-oxazol-4-yl2.6-F2C(O)Me
12112-chloro-5-fluoro-1,3-oxazol-4-yl2.6-F2C(O)Me
12122-bromo-5-fluoro-1,3-oxazol-4-yl2.6-F2C(O)Me
12135-fluoro-1,3-oxazol-2-yl2.6-F2C(O)Me
12145-chloro-1,3-oxazol-2-yl2.6-F2C(O)Me
12155-bromo-1,3-oxazol-2-yl2.6-F2C(O)Me
12164,5-difluoro-1,3-oxazol-2-yl2.6-F2C(O)Me
12174-chloro-5-fluoro-1,3-oxazol-2-yl2.6-F2C(O)Me
12184-bromo-5-fluoro-1,3-oxazol-2-yl2.6-F2C(O)Me
12195-chloro-4-fluoro-1,3-oxazol-2-yl2.6-F2C(O)Me
12205-bromo-4-fluoro-1,3-oxazol-2-yl2.6-F2C(O)Me
12212-fluoro-1,3-oxazol-5-yl2.6-F2C(O)Me
12222-chloro-1,3-oxazol-5-yl2.6-F2C(O)Me
12232-bromo-1,3-oxazol-5-yl2.6-F2C(O)Me
12242,4-difluoro-1,3-oxazol-5-yl2.6-F2C(O)Me
12254-chloro-2-fluoro-1,3-oxazol-5-yl2.6-F2C(O)Me
12264-bromo-2-fluoro-1,3-oxazol-5-yl2.6-F2C(O)Me
12272-chloro-4-fluoro-1,3-oxazol-5-yl2.6-F2C(O)Me
12282-bromo-4-fluoro-1,3-oxazol-5-yl2.6-F2C(O)Me
12291,3-thiazol-2-yl2.6-F2C(O)Me
12301,3-thiazol-5-yl2.6-F2C(O)Me
12311,3-thiazol-4-yl2.6-F2C(O)Me
12322-fluoro-1,3-thiazol-4-yl2.6-F2C(O)Me
12332-chloro-1,3-thiazol-4-yl2.6-F2C(O)Me
12342-bromo-1,3-thiazol-4-yl2.6-F2C(O)Me
12352,5-difluoro-1,3-thiazol-4-yl2.6-F2C(O)Me
12365-chloro-2-fluoro-1,3-thiazol-4-yl2.6-F2C(O)Me
12375-bromo-2-fluoro-1,3-thiazol-4-yl2.6-F2C(O)Me
12382-chloro-5-fluoro-1,3-thiazol-4-yl2.6-F2C(O)Me
12392-bromo-5-fluoro-1,3-thiazol-4-yl2.6-F2C(O)Me
12405-fluoro-1,3-thiazol-2-yl2.6-F2C(O)Me
12415-chloro-1,3-thiazol-2-yl2.6-F2C(O)Me
12425-bromo-1,3-thiazol-2-yl2.6-F2C(O)Me
12434,5-difluoro-1,3-thiazol-2-yl2.6-F2C(O)Me
12444-chloro-5-fluoro-1,3-thiazol-2-yl2.6-F2C(O)Me
12454-bromo-5-fluoro-1,3-thiazol-2-yl2.6-F2C(O)Me
12465-chloro-4-fluoro-1,3-thiazol-2-yl2.6-F2C(O)Me
12475-bromo-4-fluoro-1,3-thiazol-2-yl2.6-F2C(O)Me
12482-fluoro-1,3-thiazol-5-yl2.6-F2C(O)Me
12492-chloro-1,3-thiazol-5-yl2.6-F2C(O)Me
12502-bromo-1,3-thiazol-5-yl2.6-F2C(O)Me
12512,4-difluoro-1,3-thiazol-5-yl2.6-F2C(O)Me
12524-chloro-2-fluoro-1,3-thiazol-5-yl2.6-F2C(O)Me
12534-bromo-2-fluoro-1,3-thiazol-5-yl2.6-F2C(O)Me
12542-chloro-4-fluoro-1,3-thiazol-5-yl2.6-F2C(O)Me
12552-bromo-4-fluoro-1,3-thiazol-5-yl2.6-F2C(O)Me
12561-methyl-1H-imidazol-2-yl2.6-F2C(O)Me
12571-methyl-1H-imidazol-5-yl2.6-F2C(O)Me
12581-methyl-1H-imidazol-4-yl2.6-F2C(O)Me
12592-fluoro-1,3-1-methyl-1H-imidazol-4-yl2.6-F2C(O)Me
12602-chloro-1,3-1-methyl-1H-imidazol-4-yl2.6-F2C(O)Me
12612-bromo-1,3-1-methyl-1H-imidazol-4-yl2.6-F2C(O)Me
12622,5-difluoro-1,3-1-methyl-1H-imidazol-4-yl2.6-F2C(O)Me
12635-chloro-2-fluoro-1,3-1-methyl-1H-imidazol-4-2.6-F2C(O)Me
yl
12645-bromo-2-fluoro-1,3-1-methyl-1H-imidazol-4-2.6-F2C(O)Me
yl
12652-chloro-5-fluoro-1,3-1-methyl-1H-imidazol-4-2.6-F2C(O)Me
yl
12662-bromo-5-fluoro-1,3-1-methyl-1H-imidazol-4-2.6-F2C(O)Me
yl
12675-fluoro-1,3-1-methyl-1H-imidazol-2-yl2.6-F2C(O)Me
12685-chloro-1,3-1-methyl-1H-imidazol-2-yl2.6-F2C(O)Me
12695-bromo-1,3-1-methyl-1H-imidazol-2-yl2.6-F2C(O)Me
12704,5-difluoro-1,3-1-methyl-1H-imidazol-2-yl2.6-F2C(O)Me
12714-chloro-5-fluoro-1,3-1-methyl-1H-imidazol-2-2.6-F2C(O)Me
yl
12724-bromo-5-fluoro-1,3-1-methyl-1H-imidazol-2-2.6-F2C(O)Me
yl
12735-chloro-4-fluoro-1,3-1-methyl-1H-imidazol-2-2.6-F2C(O)Me
yl
12745-bromo-4-fluoro-1,3-1-methyl-1H-imidazol-2-2.6-F2C(O)Me
yl
12752-fluoro-1,3-1-methyl-1H-imidazol-5-yl2.6-F2C(O)Me
12762-chloro-1,3-1-methyl-1H-imidazol-5-yl2.6-F2C(O)Me
12772-bromo-1,3-1-methyl-1H-imidazol-5-yl2.6-F2C(O)Me
12782,4-difluoro-1,3-1-methyl-1H-imidazol-5-yl2.6-F2C(O)Me
12794-chloro-2-fluoro-1,3-1-methyl-1H-imidazol-5-2.6-F2C(O)Me
yl
12804-bromo-2-fluoro-1,3-1-methyl-1H-imidazol-5-2.6-F2C(O)Me
yl
12812-chloro-4-fluoro-1,3-1-methyl-1H-imidazol-5-2.6-F2C(O)Me
yl
12822-bromo-4-fluoro-1,3-1-methyl-1H-imidazol-5-2.6-F2C(O)Me
yl
12831-methyl-1H-pyrazol-5-yl2.6-F2C(O)Me
12843-fluoro-1-methyl-1H-pyrazol-5-yl2.6-F2C(O)Me
12853-chloro-1-methyl-1H-pyrazol-5-yl2.6-F2C(O)Me
12863-bromo-1-methyl-1H-pyrazol-5-yl2.6-F2C(O)Me
12874-fluoro-1-methyl-1H-pyrazol-5-yl2.6-F2C(O)Me
12884-chloro-1-methyl-1H-pyrazol-5-yl2.6-F2C(O)Me
12894-bromo-1-methyl-1H-pyrazol-5-yl2.6-F2C(O)Me
12903,4-difluoro-1-methyl-1H-pyrazol-5-yl2.6-F2C(O)Me
12914-chloro-3-fluoro-1-methyl-1H-pyrazol-5-yl2.6-F2C(O)Me
12924-bromo-3-fluoro-1-methyl-1H-pyrazol-5-yl2.6-F2C(O)Me
12933-chloro-4-fluoro-1-methyl-1H-pyrazol-5-yl2.6-F2C(O)Me
12943-bromo-4-fluoro-1-methyl-1H-pyrazol-5-yl2.6-F2C(O)Me
12951-methyl-1H-pyrazol-4-yl2.6-F2C(O)Me
12965-fluoro-1-methyl-1H-pyrazol-4-yl2.6-F2C(O)Me
12975-chloro-1-methyl-1H-pyrazol-4-yl2.6-F2C(O)Me
12985-bromo-1-methyl-1H-pyrazol-4-yl2.6-F2C(O)Me
12993-fluoro-1-methyl-1H-pyrazol-4-yl2.6-F2C(O)Me
13003-chloro-1-methyl-1H-pyrazol-4-yl2.6-F2C(O)Me
13013-bromo-1-methyl-1H-pyrazol-4-yl2.6-F2C(O)Me
13023,5-difluoro-1-methyl-1H-pyrazol-4-yl2.6-F2C(O)Me
13035-chloro-3-fluoro-1-methyl-1H-pyrazol-4-yl2.6-F2C(O)Me
13045-bromo-3-fluoro-1-methyl-1H-pyrazol-4-yl2.6-F2C(O)Me
13053-chloro-5-fluoro-1-methyl-1H-pyrazol-4-yl2.6-F2C(O)Me
13063-bromo-5-fluoro-1-methyl-1H-pyrazol-4-yl2.6-F2C(O)Me
13075-fluoro-1-methyl-1H-pyrazol-3-yl2.6-F2C(O)Me
13085-chloro-1-methyl-1H-pyrazol-3-yl2.6-F2C(O)Me
13095-bromo-1-methyl-1H-pyrazol-3-yl2.6-F2C(O)Me
13104-fluoro-1-methyl-1H-pyrazol-3-yl2.6-F2C(O)Me
13114-chloro-1-methyl-1H-pyrazol-3-yl2.6-F2C(O)Me
13124-bromo-1-methyl-1H-pyrazol-3-yl2.6-F2C(O)Me
13134,5-difluoro-1-methyl-1H-pyrazol-3-yl2.6-F2C(O)Me
13144-chloro-5-fluoro-1-methyl-1H-pyrazol-3-yl2.6-F2C(O)Me
13154-bromo-5-fluoro-1-methyl-1H-pyrazol-3-yl2.6-F2C(O)Me
13165-chloro-4-fluoro-1-methyl-1H-pyrazol-3-yl2.6-F2C(O)Me
13175-bromo-4-fluoro-1-methyl-1H-pyrazol-3-yl2.6-F2C(O)Me
13181,3,5-triazin-2-yl2.6-F2C(O)Me
13194-fluoro-1,3,5-triazin-2-yl2.6-F2C(O)Me
13204-chloro-1,3,5-triazin-2-yl2.6-F2C(O)Me
13214-bromo-1,3,5-triazin-2-yl2.6-F2C(O)Me
13224,6-difluoro-1,3,5-triazin-2-yl2.6-F2C(O)Me
13234-chloro-6-fluoro-1,3,5-triazin-2-yl2.6-F2C(O)Me
13244-bromo-6-fluoro-1,3,5-triazin-2-yl2.6-F2C(O)Me
13251,2,3-triazin-4-yl2.6-F2C(O)Me
13266-fluoro-1,2,3-triazin-4-yl2.6-F2C(O)Me
13276-chloro-1,2,3-triazin-4-yl2.6-F2C(O)Me
13286-bromo-1,2,3-triazin-4-yl2.6-F2C(O)Me
13295,6-difluoro-1,2,3-triazin-4-yl2.6-F2C(O)Me
13305-chloro-6-fluoro-1,2,3-triazin-4-yl2.6-F2C(O)Me
13315-bromo-6-fluoro-1,2,3-triazin-4-yl2.6-F2C(O)Me
13321,2,3-triazin-5-yl2.6-F2C(O)Me
13334-fluoro-1,2,3-triazin-5-yl2.6-F2C(O)Me
13344-chloro-1,2,3-triazin-5-yl2.6-F2C(O)Me
13354-bromo-1,2,3-triazin-5-yl2.6-F2C(O)Me
13364,6-difluoro-1,2,3-triazin-5-yl2.6-F2C(O)Me
13374-chloro-6-fluoro-1,2,3-triazin-5-yl2.6-F2C(O)Me
13384-bromo-6-fluoro-1,2,3-triazin-5-yl2.6-F2C(O)Me
13391,2,4-triazin-5-yl2.6-F2C(O)Me
13403-fluoro-1,2,4-triazin-5-yl2.6-F2C(O)Me
13413-chloro-1,2,4-triazin-5-yl2.6-F2C(O)Me
13423-bromo-1,2,4-triazin-5-yl2.6-F2C(O)Me
13436-fluoro-1,2,4-triazin-5-yl2.6-F2C(O)Me
13446-chloro-1,2,4-triazin-5-yl2.6-F2C(O)Me
13456-bromo-1,2,4-triazin-5-yl2.6-F2C(O)Me
13463,6-difluoro-1,2,4-triazin-5-yl2.6-F2C(O)Me
13476-chloro-3-fluoro-1,2,4-triazin-5-yl2.6-F2C(O)Me
13486-bromo-3-fluoro-1,2,4-triazin-5-yl2.6-F2C(O)Me
13493-chloro-6-fluoro-1,2,4-triazin-5-yl2.6-F2C(O)Me
13503-bromo-6-fluoro-1,2,4-triazin-5-yl2.6-F2C(O)Me
13511,2,4-triazin-3-yl2.6-F2C(O)Me
13526-fluoro-1,2,4-triazin-3-yl2.6-F2C(O)Me
13536-chloro-1,2,4-triazin-3-yl2.6-F2C(O)Me
13546-bromo-1,2,4-triazin-3-yl2.6-F2C(O)Me
13555-fluoro-1,2,4-triazin-3-yl2.6-F2C(O)Me
13565-chloro-1,2,4-triazin-3-yl2.6-F2C(O)Me
13575-bromo-1,2,4-triazin-3-yl2.6-F2C(O)Me
13585-chloro-6-fluoro-1,2,4-triazin-3-yl2.6-F2C(O)Me
13595-bromo-6-fluoro-1,2,4-triazin-3-yl2.6-F2C(O)Me
13605,6-difluoro-1,2,4-triazin-3-yl2.6-F2C(O)Me
13616-chloro-5-fluoro-1,2,4-triazin-3-yl2.6-F2C(O)Me
13626-bromo-5-fluoro-1,2,4-triazin-3-yl2.6-F2C(O)Me
13631,2,4-triazin-6-yl2.6-F2C(O)Me
13643-fluoro-1,2,4-triazin-6-yl2.6-F2C(O)Me
13653-chloro-1,2,4-triazin-6-yl2.6-F2C(O)Me
13663-bromo-1,2,4-triazin-6-yl2.6-F2C(O)Me
13675-fluoro-1,2,4-triazin-6-yl2.6-F2C(O)Me
13685-chloro-1,2,4-triazin-6-yl2.6-F2C(O)Me
13695-bromo-1,2,4-triazin-6-yl2.6-F2C(O)Me
13703,5-difluoro-1,2,4-triazin-6-yl2.6-F2C(O)Me
13715-chloro-3-fluoro-1,2,4-triazin-6-yl2.6-F2C(O)Me
13725-bromo-3-fluoro-1,2,4-triazin-6-yl2.6-F2C(O)Me
13733-chloro-5-fluoro-1,2,4-triazin-6-yl2.6-F2C(O)Me
13743-bromo-5-fluoro-1,2,4-triazin-6-yl2.6-F2C(O)Me
13756-fluoropyridin-3-yl2.5-F2C(O)Me
13766-chloropyridin-3-yl2.5-F2C(O)Me
13776-bromopyridin-3-yl2.5-F2C(O)Me
13785-fluoropyridin-3-yl2.5-F2C(O)Me
13795-chloropyridin-3-yl2.5-F2C(O)Me
13805-bromopyridin-3-yl2.5-F2C(O)Me
13814-fluoropyridin-3-yl2.5-F2C(O)Me
13824-chloropyridin-3-yl2.5-F2C(O)Me
13834-bromopyridin-3-yl2.5-F2C(O)Me
13842-fluoropyridin-3-yl2.5-F2C(O)Me
13852-chloropyridin-3-yl2.5-F2C(O)Me
13862-bromopyridin-3-yl2.5-F2C(O)Me
13872,6-difluoropyridin-3-yl2.5-F2C(O)Me
13885-chloro-6-fluoropyridin-3-yl2.5-F2C(O)Me
13895-bromo-6-fluoropyridin-3-yl2.5-F2C(O)Me
13905,6-difluoropyridin-3-yl2.5-F2C(O)Me
13916-chloro-5-fluoropyridin-3-yl2.5-F2C(O)Me
13926-bromo-5-fluoropyridin-3-yl2.5-F2C(O)Me
13934,5-difluoropyridin-3-yl2.5-F2C(O)Me
13944-chloro-5-fluoropyridin-3-yl2.5-F2C(O)Me
13954-bromo-5-fluoropyridin-3-yl2.5-F2C(O)Me
13965-chloro-4-fluoropyridin-3-yl2.5-F2C(O)Me
13974,5-dichloropyridin-3-yl2.5-F2C(O)Me
13984-bromo-5-chloropyridin-3-yl2.5-F2C(O)Me
13995-bromo-4-fluoropyridin-3-yl2.5-F2C(O)Me
14005-bromo-4-chloropyridin-3-yl2.5-F2C(O)Me
14014,5-dibromopyridin-3-yl2.5-F2C(O)Me
14022,3-difluoropyridin-4-yl2.5-F2C(O)Me
14033-chloro-2-fluoropyridin-4-yl2.5-F2C(O)Me
14043-bromo-2-fluoropyridin-4-yl2.5-F2C(O)Me
14052-fluoropyridin-4-yl2.5-F2C(O)Me
14062-chloropyridin-4-yl2.5-F2C(O)Me
14072-bromopyridin-4-yl2.5-F2C(O)Me
14082,6-difluoropyridin-4-yl2.5-F2C(O)Me
14092-chloro-6-fluoropyridin-4-yl2.5-F2C(O)Me
14102-bromo-6-fluoropyridin-4-yl2.5-F2C(O)Me
14112,3,6-trifluoropyridin-4-yl2.5-F2C(O)Me
14123-chloro-2,6-difluoropyridin-4-yl2.5-F2C(O)Me
14133-bromo-2,6-difluoropyridin-4-yl2.5-F2C(O)Me
14142-chloro-3,6-difluoropyridin-4-yl2.5-F2C(O)Me
14152-bromo-3,6-difluoropyridin-4-yl2.5-F2C(O)Me
14166-chloro-2,3-difluoropyridin-4-yl2.5-F2C(O)Me
14176-bromo-2,3-difluoropyridin-4-yl2.5-F2C(O)Me
14182,5,6-trifluoropyridin-3-yl2.5-F2C(O)Me
14192-chloro-5,6-difluoropyridin-3-yl2.5-F2C(O)Me
14202-bromo-5,6-difluoropyridin-3-yl2.5-F2C(O)Me
14216-chloro-2,5-difluoropyridin-3-yl2.5-F2C(O)Me
14226-bromo-2,5-difluoropyridin-3-yl2.5-F2C(O)Me
14235-chloro-2,6-difluoropyridin-3-yl2.5-F2C(O)Me
14245-bromo-2,6-difluoropyridin-3-yl2.5-F2C(O)Me
14256-fluoropyridin-2-yl2.5-F2C(O)Me
14266-chloropyridin-2-yl2.5-F2C(O)Me
14276-bromopyridin-2-yl2.5-F2C(O)Me
14285-fluoropyridin-2-yl2.5-F2C(O)Me
14295-chloropyridin-2-yl2.5-F2C(O)Me
14305-bromopyridin-2-yl2.5-F2C(O)Me
14314-fluoropyridin-2-yl2.5-F2C(O)Me
14324-chloropyridin-2-yl2.5-F2C(O)Me
14334-bromopyridin-2-yl2.5-F2C(O)Me
14343-fluoropyridin-2-yl2.5-F2C(O)Me
14353-chloropyridin-2-yl2.5-F2C(O)Me
14363-bromopyridin-2-yl2.5-F2C(O)Me
14373,4-difluoropyridin-2-yl2.5-F2C(O)Me
14384-chloro-3-fluoropyridin-2-yl2.5-F2C(O)Me
14394-bromo-3-fluoropyridin-2-yl2.5-F2C(O)Me
14403,5-difluoropyridin-2-yl2.5-F2C(O)Me
14415-chloro-3-fluoropyridin-2-yl2.5-F2C(O)Me
14425-bromo-3-fluoropyridin-2-yl2.5-F2C(O)Me
14433,6-difluoropyridin-2-yl2.5-F2C(O)Me
14446-chloro-3-fluoropyridin-2-yl2.5-F2C(O)Me
14456-bromo-3-fluoropyridin-2-yl2.5-F2C(O)Me
14463,4,6-trifluoropyridin-2-yl2.5-F2C(O)Me
14474-chloro-3,6-difluoropyridin-2-yl2.5-F2C(O)Me
14484-bromo-3,6-difluoropyridin-2-yl2.5-F2C(O)Me
14493,5,6-trifluoropyridin-2-yl2.5-F2C(O)Me
14505-chloro-3,6-difluoropyridin-2-yl2.5-F2C(O)Me
14515-bromo-3,6-difluoropyridin-2-yl2.5-F2C(O)Me
14524,5,6-trifluoropyridin-3-yl2.5-F2C(O)Me
14534-chloro-5,6-difluoropyridin-3-yl2.5-F2C(O)Me
14544-bromo-5,6-difluoropyridin-3-yl2.5-F2C(O)Me
14555-chloro-4,6-difluoropyridin-3-yl2.5-F2C(O)Me
14565-bromo-4,6-difluoropyridin-3-yl2.5-F2C(O)Me
14576-chloro-4,5-difluoropyridin-3-yl2.5-F2C(O)Me
14586-bromo-4,5-difluoropyridin-3-yl2.5-F2C(O)Me
1459pyridin-3-yl2.5-F2C(O)Me
1460pyridin-2-yl2.5-F2C(O)Me
1461pyridin-4-yl2.5-F2C(O)Me
14622-fluoropyrimidin-4-yl2.5-F2C(O)Me
14632-chloropyrimidin-4-yl2.5-F2C(O)Me
14642-bromopyrimidin-4-yl2.5-F2C(O)Me
14652,6-difluoropyrimidin-4-yl2.5-F2C(O)Me
14666-chloro-2-fluoropyrimidin-4-yl2.5-F2C(O)Me
14676-bromo-2-fluoropyrimidin-4-yl2.5-F2C(O)Me
14686-fluoropyrimidin-4-yl2.5-F2C(O)Me
14696-chloropyrimidin-4-yl2.5-F2C(O)Me
14706-bromopyrimidin-4-yl2.5-F2C(O)Me
14714-fluoropyrimidin-2-yl2.5-F2C(O)Me
14724-chloropyrimidin-2-yl2.5-F2C(O)Me
14734-bromopyrimidin-2-yl2.5-F2C(O)Me
14744,5-difluoropyrimidin-2-yl2.5-F2C(O)Me
14755-chloro-4-fluoropyrimidin-2-yl2.5-F2C(O)Me
14765-bromo-4-fluoropyrimidin-2-yl2.5-F2C(O)Me
14774-chloro-5-fluoropyrimidin-2-yl2.5-F2C(O)Me
14784-bromo-5-fluoropyrimidin-2-yl2.5-F2C(O)Me
14794,6-difluoropyrimidin-2-yl2.5-F2C(O)Me
14804-chloro-6-fluoropyrimidin-2-yl2.5-F2C(O)Me
14814-bromo-6-fluoropyrimidin-2-yl2.5-F2C(O)Me
1482pyrimidin-2-yl2.5-F2C(O)Me
1483pyrimidin-4-yl2.5-F2C(O)Me
1484pyrimidin-5-yl2.5-F2C(O)Me
14852,4-difluoropyrimidin-5-yl2.5-F2C(O)Me
14864-chloro-2-fluoropyrimidin-5-yl2.5-F2C(O)Me
14874-bromo-2-fluoropyrimidin-5-yl2.5-F2C(O)Me
14882-fluoropyrimidin-5-yl2.5-F2C(O)Me
14892-chloropyrimidin-5-yl2.5-F2C(O)Me
14902-bromopyrimidin-5-yl2.5-F2C(O)Me
1491pyridazin-3-yl2.5-F2C(O)Me
1492pyridazin-4-yl2.5-F2C(O)Me
14936-fluoropyridazin-4-yl2.5-F2C(O)Me
14946-chloropyridazin-4-yl2.5-F2C(O)Me
14956-bromopyridazin-4-yl2.5-F2C(O)Me
14965,6-difluoropyridazin-4-yl2.5-F2C(O)Me
14975-chloro-6-fluoropyridazin-4-yl2.5-F2C(O)Me
14985-bromo-6-fluoropyridazin-4-yl2.5-F2C(O)Me
14996-chloro-5-fluoropyridazin-4-yl2.5-F2C(O)Me
15006-bromo-5-fluoropyridazin-4-yl2.5-F2C(O)Me
15013,5-difluoropyridazin-4-yl2.5-F2C(O)Me
15023-chloro-5-fluoropyridazin-4-yl2.5-F2C(O)Me
15033-bromo-5-fluoropyridazin-4-yl2.5-F2C(O)Me
15045-chloro-3-fluoropyridazin-4-yl2.5-F2C(O)Me
15055-bromo-3-fluoropyridazin-4-yl2.5-F2C(O)Me
15063,6-difluoropyridazin-4-yl2.5-F2C(O)Me
15076-chloro-3-fluoropyridazin-4-yl2.5-F2C(O)Me
15086-bromo-3-fluoropyridazin-4-yl2.5-F2C(O)Me
15093-chloro-6-fluoropyridazin-4-yl2.5-F2C(O)Me
15103-bromo-6-fluoropyridazin-4-yl2.5-F2C(O)Me
15116-fluoropyridazin-3-yl2.5-F2C(O)Me
15126-chloropyridazin-3-yl2.5-F2C(O)Me
15136-bromopyridazin-3-yl2.5-F2C(O)Me
15145-fluoropyridazin-3-yl2.5-F2C(O)Me
15155-chloropyridazin-3-yl2.5-F2C(O)Me
15165-bromopyridazin-3-yl2.5-F2C(O)Me
15174-fluoropyridazin-3-yl2.5-F2C(O)Me
15184-chloropyridazin-3-yl2.5-F2C(O)Me
15194-bromopyridazin-3-yl2.5-F2C(O)Me
15205,6-difluoropyridazin-3-yl2.5-F2C(O)Me
15215-chloro-6-fluoropyridazin-3-yl2.5-F2C(O)Me
15225-bromo-6-fluoropyridazin-3-yl2.5-F2C(O)Me
15236-chloro-5-fluoropyridazin-3-yl2.5-F2C(O)Me
15246-bromo-5-fluoropyridazin-3-yl2.5-F2C(O)Me
15254,6-difluoropyridazin-3-yl2.5-F2C(O)Me
15264-chloro-6-fluoropyridazin-3-yl2.5-F2C(O)Me
15274-bromo-6-fluoropyridazin-3-yl2.5-F2C(O)Me
15286-chloro-4-fluoropyridazin-3-yl2.5-F2C(O)Me
15296-bromo-4-fluoropyridazin-3-yl2.5-F2C(O)Me
15304,5-difluoropyridazin-3-yl2.5-F2C(O)Me
15315-chloro-4-fluoropyridazin-3-yl2.5-F2C(O)Me
15325-bromo-4-fluoropyridazin-3-yl2.5-F2C(O)Me
15334-chloro-5-fluoropyridazin-3-yl2.5-F2C(O)Me
15344-bromo-5-fluoropyridazin-3-yl2.5-F2C(O)Me
1535pyrazin-2-yl2.5-F2C(O)Me
15363-fluoropyrazin-2-yl2.5-F2C(O)Me
15373-chloropyrazin-2-yl2.5-F2C(O)Me
15383-bromopyrazin-2-yl2.5-F2C(O)Me
15396-fluoropyrazin-2-yl2.5-F2C(O)Me
15406-chloropyrazin-2-yl2.5-F2C(O)Me
15416-bromopyrazin-2-yl2.5-F2C(O)Me
15425-fluoropyrazin-2-yl2.5-F2C(O)Me
15435-chloropyrazin-2-yl2.5-F2C(O)Me
15445-bromopyrazin-2-yl2.5-F2C(O)Me
15455,6-difluoropyrazin-2-yl2.5-F2C(O)Me
15465-chloro-6-fluoropyrazin-2-yl2.5-F2C(O)Me
15475-bromo-6-fluoropyrazin-2-yl2.5-F2C(O)Me
15486-chloro-5-fluoropyrazin-2-yl2.5-F2C(O)Me
15496-bromo-5-fluoropyrazin-2-yl2.5-F2C(O)Me
15503,5-difluoropyrazin-2-yl2.5-F2C(O)Me
15513-chloro-5-fluoropyrazin-2-yl2.5-F2C(O)Me
15523-bromo-5-fluoropyrazin-2-yl2.5-F2C(O)Me
15535-chloro-3-fluoropyrazin-2-yl2.5-F2C(O)Me
15545-bromo-3-fluoropyrazin-2-yl2.5-F2C(O)Me
15553,6-difluoropyrazin-2-yl2.5-F2C(O)Me
15566-chloro-3-fluoropyrazin-2-yl2.5-F2C(O)Me
15576-bromo-3-fluoropyrazin-2-yl2.5-F2C(O)Me
15583-chloro-6-fluoropyrazin-2-yl2.5-F2C(O)Me
15593-bromo-6-fluoropyrazin-2-yl2.5-F2C(O)Me
15602-thienyl2.5-F2C(O)Me
15615-fluoro-2-thienyl2.5-F2C(O)Me
15625-chloro-2-thienyl2.5-F2C(O)Me
15635-bromo-2-thienyl2.5-F2C(O)Me
15644-fluoro-2-thienyl2.5-F2C(O)Me
15654-chloro-2-thienyl2.5-F2C(O)Me
15664-bromo-2-thienyl2.5-F2C(O)Me
15672-fluoro-2-thienyl2.5-F2C(O)Me
15683-chloro-2-thienyl2.5-F2C(O)Me
15693-bromo-2-thienyl2.5-F2C(O)Me
15703-thienyl2.5-F2C(O)Me
15712-fluoro-3-thienyl2.5-F2C(O)Me
15722-chloro-3-thienyl2.5-F2C(O)Me
15732-bromo-3-thienyl2.5-F2C(O)Me
15745-fluoro-3-thienyl2.5-F2C(O)Me
15755-chloro-3-thienyl2.5-F2C(O)Me
15765-bromo-3-thienyl2.5-F2C(O)Me
15774-fluoro-3-thienyl2.5-F2C(O)Me
15784-chloro-3-thienyl2.5-F2C(O)Me
15794-bromo-3-thienyl2.5-F2C(O)Me
15802,4-difluoro-3-thienyl2.5-F2C(O)Me
15812-chloro-4-fluoro-3-thienyl2.5-F2C(O)Me
15822-bromo-4-fluoro-3-thienyl2.5-F2C(O)Me
15834-chloro-2-fluoro-3-thienyl2.5-F2C(O)Me
15844-bromo-2-fluoro-3-thienyl2.5-F2C(O)Me
15852,5-difluoro-3-thienyl2.5-F2C(O)Me
15865-chloro-2-fluoro-3-thienyl2.5-F2C(O)Me
15875-bromo-2-fluoro-3-thienyl2.5-F2C(O)Me
15882-chloro-5-fluoro-3-thienyl2.5-F2C(O)Me
15892-bromo-5-fluoro-3-thienyl2.5-F2C(O)Me
15904,5-difluoro-3-thienyl2.5-F2C(O)Me
15914-chloro-5-fluoro-3-thienyl2.5-F2C(O)Me
15924-bromo-5-fluoro-3-thienyl2.5-F2C(O)Me
15935-chloro-4-fluoro-3-thienyl2.5-F2C(O)Me
15945-bromo-4-fluoro-3-thienyl2.5-F2C(O)Me
15953,4-difluoro-2-thienyl2.5-F2C(O)Me
15964-chloro-3-fluoro-2-thienyl2.5-F2C(O)Me
15974-bromo-3-fluoro-2-thienyl2.5-F2C(O)Me
15983-chloro-4-fluoro-2-thienyl2.5-F2C(O)Me
15993-bromo-4-fluoro-2-thienyl2.5-F2C(O)Me
16003,5-difluoro-2-thienyl2.5-F2C(O)Me
16015-chloro-3-fluoro-2-thienyl2.5-F2C(O)Me
16025-bromo-3-fluoro-2-thienyl2.5-F2C(O)Me
16033-chloro-5-fluoro-2-thienyl2.5-F2C(O)Me
16043-bromo-5-fluoro-2-thienyl2.5-F2C(O)Me
16054,5-difluoro-2-thienyl2.5-F2C(O)Me
16064-chloro-5-fluoro-2-thienyl2.5-F2C(O)Me
16074-bromo-5-fluoro-2-thienyl2.5-F2C(O)Me
16085-chloro-4-fluoro-2-thienyl2.5-F2C(O)Me
16095-bromo-4-fluoro-2-thienyl2.5-F2C(O)Me
16102-furyl2.5-F2C(O)Me
16115-fluoro-2-furyl2.5-F2C(O)Me
16125-chloro-2-furyl2.5-F2C(O)Me
16135-bromo-2-furyl2.5-F2C(O)Me
16144-fluoro-2-furyl2.5-F2C(O)Me
16154-chloro-2-furyl2.5-F2C(O)Me
16164-bromo-2-furyl2.5-F2C(O)Me
16172-fluoro-2-furyl2.5-F2C(O)Me
16183-chloro-2-furyl2.5-F2C(O)Me
16193-bromo-2-furyl2.5-F2C(O)Me
16203-furyl2.5-F2C(O)Me
16212-fluoro-3-furyl2.5-F2C(O)Me
16222-chloro-3-furyl2.5-F2C(O)Me
16232-bromo-3-furyl2.5-F2C(O)Me
16245-fluoro-3-furyl2.5-F2C(O)Me
16255-chloro-3-furyl2.5-F2C(O)Me
16265-bromo-3-furyl2.5-F2C(O)Me
16274-fluoro-3-furyl2.5-F2C(O)Me
16284-chloro-3-furyl2.5-F2C(O)Me
16294-bromo-3-furyl2.5-F2C(O)Me
16302,4-difluoro-3-furyl2.5-F2C(O)Me
16312-chloro-4-fluoro-3-furyl2.5-F2C(O)Me
16322-bromo-4-fluoro-3-furyl2.5-F2C(O)Me
16334-chloro-2-fluoro-3-furyl2.5-F2C(O)Me
16344-bromo-2-fluoro-3-furyl2.5-F2C(O)Me
16352,5-difluoro-3-furyl2.5-F2C(O)Me
16365-chloro-2-fluoro-3-furyl2.5-F2C(O)Me
16375-bromo-2-fluoro-3-furyl2.5-F2C(O)Me
16382-chloro-5-fluoro-3-furyl2.5-F2C(O)Me
16392-bromo-5-fluoro-3-furyl2.5-F2C(O)Me
16404,5-difluoro-3-furyl2.5-F2C(O)Me
16414-chloro-5-fluoro-3-furyl2.5-F2C(O)Me
16424-bromo-5-fluoro-3-furyl2.5-F2C(O)Me
16435-chloro-4-fluoro-3-furyl2.5-F2C(O)Me
16445-bromo-4-fluoro-3-furyl2.5-F2C(O)Me
16453,4-difluoro-2-furyl2.5-F2C(O)Me
16464-chloro-3-fluoro-2-furyl2.5-F2C(O)Me
16474-bromo-3-fluoro-2-furyl2.5-F2C(O)Me
16483-chloro-4-fluoro-2-furyl2.5-F2C(O)Me
16493-bromo-4-fluoro-2-furyl2.5-F2C(O)Me
16503,5-difluoro-2-furyl2.5-F2C(O)Me
16515-chloro-3-fluoro-2-furyl2.5-F2C(O)Me
16525-bromo-3-fluoro-2-furyl2.5-F2C(O)Me
16533-chloro-5-fluoro-2-furyl2.5-F2C(O)Me
16543-bromo-5-fluoro-2-furyl2.5-F2C(O)Me
16554,5-difluoro-2-furyl2.5-F2C(O)Me
16564-chloro-5-fluoro-2-furyl2.5-F2C(O)Me
16574-bromo-5-fluoro-2-furyl2.5-F2C(O)Me
16585-chloro-4-fluoro-2-furyl2.5-F2C(O)Me
16595-bromo-4-fluoro-2-furyl2.5-F2C(O)Me
16601,3-oxazol-2-yl2.5-F2C(O)Me
16611,3-oxazol-5-yl2.5-F2C(O)Me
16621,3-oxazol-4-yl2.5-F2C(O)Me
16632-fluoro-1,3-oxazol-4-yl2.5-F2C(O)Me
16642-chloro-1,3-oxazol-4-yl2.5-F2C(O)Me
16652-bromo-1,3-oxazol-4-yl2.5-F2C(O)Me
16662,5-difluoro-1,3-oxazol-4-yl2.5-F2C(O)Me
16675-chloro-2-fluoro-1,3-oxazol-4-yl2.5-F2C(O)Me
16685-bromo-2-fluoro-1,3-oxazol-4-yl2.5-F2C(O)Me
16692-chloro-5-fluoro-1,3-oxazol-4-yl2.5-F2C(O)Me
16702-bromo-5-fluoro-1,3-oxazol-4-yl2.5-F2C(O)Me
16715-fluoro-1,3-oxazol-2-yl2.5-F2C(O)Me
16725-chloro-1,3-oxazol-2-yl2.5-F2C(O)Me
16735-bromo-1,3-oxazol-2-yl2.5-F2C(O)Me
16744,5-difluoro-1,3-oxazol-2-yl2.5-F2C(O)Me
16754-chloro-5-fluoro-1,3-oxazol-2-yl2.5-F2C(O)Me
16764-bromo-5-fluoro-1,3-oxazol-2-yl2.5-F2C(O)Me
16775-chloro-4-fluoro-1,3-oxazol-2-yl2.5-F2C(O)Me
16785-bromo-4-fluoro-1,3-oxazol-2-yl2.5-F2C(O)Me
16792-fluoro-1,3-oxazol-5-yl2.5-F2C(O)Me
16802-chloro-1,3-oxazol-5-yl2.5-F2C(O)Me
16812-bromo-1,3-oxazol-5-yl2.5-F2C(O)Me
16822,4-difluoro-1,3-oxazol-5-yl2.5-F2C(O)Me
16834-chloro-2-fluoro-1,3-oxazol-5-yl2.5-F2C(O)Me
16844-bromo-2-fluoro-1,3-oxazol-5-yl2.5-F2C(O)Me
16852-chloro-4-fluoro-1,3-oxazol-5-yl2.5-F2C(O)Me
16862-bromo-4-fluoro-1,3-oxazol-5-yl2.5-F2C(O)Me
16871,3-thiazol-2-yl2.5-F2C(O)Me
16881,3-thiazol-5-yl2.5-F2C(O)Me
16891,3-thiazol-4-yl2.5-F2C(O)Me
16902-fluoro-1,3-thiazol-4-yl2.5-F2C(O)Me
16912-chloro-1,3-thiazol-4-yl2.5-F2C(O)Me
16922-bromo-1,3-thiazol-4-yl2.5-F2C(O)Me
16932,5-difluoro-1,3-thiazol-4-yl2.5-F2C(O)Me
16945-chloro-2-fluoro-1,3-thiazol-4-yl2.5-F2C(O)Me
16955-bromo-2-fluoro-1,3-thiazol-4-yl2.5-F2C(O)Me
16962-chloro-5-fluoro-1,3-thiazol-4-yl2.5-F2C(O)Me
16972-bromo-5-fluoro-1,3-thiazol-4-yl2.5-F2C(O)Me
16985-fluoro-1,3-thiazol-2-yl2.5-F2C(O)Me
16995-chloro-1,3-thiazol-2-yl2.5-F2C(O)Me
17005-bromo-1,3-thiazol-2-yl2.5-F2C(O)Me
17014,5-difluoro-1,3-thiazol-2-yl2.5-F2C(O)Me
17024-chloro-5-fluoro-1,3-thiazol-2-yl2.5-F2C(O)Me
17034-bromo-5-fluoro-1,3-thiazol-2-yl2.5-F2C(O)Me
17045-chloro-4-fluoro-1,3-thiazol-2-yl2.5-F2C(O)Me
17055-bromo-4-fluoro-1,3-thiazol-2-yl2.5-F2C(O)Me
17062-fluoro-1,3-thiazol-5-yl2.5-F2C(O)Me
17072-chloro-1,3-thiazol-5-yl2.5-F2C(O)Me
17082-bromo-1,3-thiazol-5-yl2.5-F2C(O)Me
17092,4-difluoro-1,3-thiazol-5-yl2.5-F2C(O)Me
17104-chloro-2-fluoro-1,3-thiazol-5-yl2.5-F2C(O)Me
17114-bromo-2-fluoro-1,3-thiazol-5-yl2.5-F2C(O)Me
17122-chloro-4-fluoro-1,3-thiazol-5-yl2.5-F2C(O)Me
17132-bromo-4-fluoro-1,3-thiazol-5-yl2.5-F2C(O)Me
17141-methyl-1H-imidazol-2-yl2.5-F2C(O)Me
17151-methyl-1H-imidazol-5-yl2.5-F2C(O)Me
17161-methyl-1H-imidazol-4-yl2.5-F2C(O)Me
17172-fluoro-1,3-1-methyl-1H-imidazol-4-yl2.5-F2C(O)Me
17182-chloro-1,3-1-methyl-1H-imidazol-4-yl2.5-F2C(O)Me
17192-bromo-1,3-1-methyl-1H-imidazol-4-yl2.5-F2C(O)Me
17202,5-difluoro-1,3-1-methyl-1H-imidazol-4-yl2.5-F2C(O)Me
17215-chloro-2-fluoro-1,3-1-methyl-1H-imidazol-4-2.5-F2C(O)Me
yl
17225-bromo-2-fluoro-1,3-1-methyl-1H-imidazol-4-2.5-F2C(O)Me
yl
17232-chloro-5-fluoro-1,3-1-methyl-1H-imidazol-4-2.5-F2C(O)Me
yl
17242-bromo-5-fluoro-1,3-1-methyl-1H-imidazol-4-2.5-F2C(O)Me
yl
17255-fluoro-1,3-1-methyl-1H-imidazol-2-yl2.5-F2C(O)Me
17265-chloro-1,3-1-methyl-1H-imidazol-2-yl2.5-F2C(O)Me
17275-bromo-1,3-1-methyl-1H-imidazol-2-yl2.5-F2C(O)Me
17284,5-difluoro-1,3-1-methyl-1H-imidazol-2-yl2.5-F2C(O)Me
17294-chloro-5-fluoro-1,3-1-methyl-1H-imidazol-2-2.5-F2C(O)Me
yl
17304-bromo-5-fluoro-1,3-1-methyl-1H-imidazol-2-2.5-F2C(O)Me
yl
17315-chloro-4-fluoro-1,3-1-methyl-1H-imidazol-2-2.5-F2C(O)Me
yl
17325-bromo-4-fluoro-1,3-1-methyl-1H-imidazol-2-2.5-F2C(O)Me
yl
17332-fluoro-1,3-1-methyl-1H-imidazol-5-yl2.5-F2C(O)Me
17342-chloro-1,3-1-methyl-1H-imidazol-5-yl2.5-F2C(O)Me
17352-bromo-1,3-1-methyl-1H-imidazol-5-yl2.5-F2C(O)Me
17362,4-difluoro-1,3-1-methyl-1H-imidazol-5-yl2.5-F2C(O)Me
17374-chloro-2-fluoro-1,3-1-methyl-1H-imidazol-5-2.5-F2C(O)Me
yl
17384-bromo-2-fluoro-1,3-1-methyl-1H-imidazol-5-2.5-F2C(O)Me
yl
17392-chloro-4-fluoro-1,3-1-methyl-1H-imidazol-5-2.5-F2C(O)Me
yl
17402-bromo-4-fluoro-1,3-1-methyl-1H-imidazol-5-2.5-F2C(O)Me
yl
17411-methyl-1H-pyrazol-5-yl2.5-F2C(O)Me
17423-fluoro-1-methyl-1H-pyrazol-5-yl2.5-F2C(O)Me
17433-chloro-1-methyl-1H-pyrazol-5-yl2.5-F2C(O)Me
17443-bromo-1-methyl-1H-pyrazol-5-yl2.5-F2C(O)Me
17454-fluoro-1-methyl-1H-pyrazol-5-yl2.5-F2C(O)Me
17464-chloro-1-methyl-1H-pyrazol-5-yl2.5-F2C(O)Me
17474-bromo-1-methyl-1H-pyrazol-5-yl2.5-F2C(O)Me
17483,4-difluoro-1-methyl-1H-pyrazol-5-yl2.5-F2C(O)Me
17494-chloro-3-fluoro-1-methyl-1H-pyrazol-5-yl2.5-F2C(O)Me
17504-bromo-3-fluoro-1-methyl-1H-pyrazol-5-yl2.5-F2C(O)Me
17513-chloro-4-fluoro-1-methyl-1H-pyrazol-5-yl2.5-F2C(O)Me
17523-bromo-4-fluoro-1-methyl-1H-pyrazol-5-yl2.5-F2C(O)Me
17531-methyl-1H-pyrazol-4-yl2.5-F2C(O)Me
17545-fluoro-1-methyl-1H-pyrazol-4-yl2.5-F2C(O)Me
17555-chloro-1-methyl-1H-pyrazol-4-yl2.5-F2C(O)Me
17565-bromo-1-methyl-1H-pyrazol-4-yl2.5-F2C(O)Me
17573-fluoro-1-methyl-1H-pyrazol-4-yl2.5-F2C(O)Me
17583-chloro-1-methyl-1H-pyrazol-4-yl2.5-F2C(O)Me
17593-bromo-1-methyl-1H-pyrazol-4-yl2.5-F2C(O)Me
17603,5-difluoro-1-methyl-1H-pyrazol-4-yl2.5-F2C(O)Me
17615-chloro-3-fluoro-1-methyl-1H-pyrazol-4-yl2.5-F2C(O)Me
17625-bromo-3-fluoro-1-methyl-1H-pyrazol-4-yl2.5-F2C(O)Me
17633-chloro-5-fluoro-1-methyl-1H-pyrazol-4-yl2.5-F2C(O)Me
17643-bromo-5-fluoro-1-methyl-1H-pyrazol-4-yl2.5-F2C(O)Me
17655-fluoro-1-methyl-1H-pyrazol-3-yl2.5-F2C(O)Me
17665-chloro-1-methyl-1H-pyrazol-3-yl2.5-F2C(O)Me
17675-bromo-1-methyl-1H-pyrazol-3-yl2.5-F2C(O)Me
17684-fluoro-1-methyl-1H-pyrazol-3-yl2.5-F2C(O)Me
17694-chloro-1-methyl-1H-pyrazol-3-yl2.5-F2C(O)Me
17704-bromo-1-methyl-1H-pyrazol-3-yl2.5-F2C(O)Me
17714,5-difluoro-1-methyl-1H-pyrazol-3-yl2.5-F2C(O)Me
17724-chloro-5-fluoro-1-methyl-1H-pyrazol-3-yl2.5-F2C(O)Me
17734-bromo-5-fluoro-1-methyl-1H-pyrazol-3-yl2.5-F2C(O)Me
17745-chloro-4-fluoro-1-methyl-1H-pyrazol-3-yl2.5-F2C(O)Me
17755-bromo-4-fluoro-1-methyl-1H-pyrazol-3-yl2.5-F2C(O)Me
17761,3,5-triazin-2-yl2.5-F2C(O)Me
17774-fluoro-1,3,5-triazin-2-yl2.5-F2C(O)Me
17784-chloro-1,3,5-triazin-2-yl2.5-F2C(O)Me
17794-bromo-1,3,5-triazin-2-yl2.5-F2C(O)Me
17804,6-difluoro-1,3,5-triazin-2-yl2.5-F2C(O)Me
17814-chloro-6-fluoro-1,3,5-triazin-2-yl2.5-F2C(O)Me
17824-bromo-6-fluoro-1,3,5-triazin-2-yl2.5-F2C(O)Me
17831,2,3-triazin-4-yl2.5-F2C(O)Me
17846-fluoro-1,2,3-triazin-4-yl2.5-F2C(O)Me
17856-chloro-1,2,3-triazin-4-yl2.5-F2C(O)Me
17866-bromo-1,2,3-triazin-4-yl2.5-F2C(O)Me
17875,6-difluoro-1,2,3-triazin-4-yl2.5-F2C(O)Me
17885-chloro-6-fluoro-1,2,3-triazin-4-yl2.5-F2C(O)Me
17895-bromo-6-fluoro-1,2,3-triazin-4-yl2.5-F2C(O)Me
17901,2,3-triazin-5-yl2.5-F2C(O)Me
17914-fluoro-1,2,3-triazin-5-yl2.5-F2C(O)Me
17924-chloro-1,2,3-triazin-5-yl2.5-F2C(O)Me
17934-bromo-1,2,3-triazin-5-yl2.5-F2C(O)Me
17944,6-difluoro-1,2,3-triazin-5-yl2.5-F2C(O)Me
17954-chloro-6-fluoro-1,2,3-triazin-5-yl2.5-F2C(O)Me
17964-bromo-6-fluoro-1,2,3-triazin-5-yl2.5-F2C(O)Me
17971,2,4-triazin-5-yl2.5-F2C(O)Me
17983-fluoro-1,2,4-triazin-5-yl2.5-F2C(O)Me
17993-chloro-1,2,4-triazin-5-yl2.5-F2C(O)Me
18003-bromo-1,2,4-triazin-5-yl2.5-F2C(O)Me
18016-fluoro-1,2,4-triazin-5-yl2.5-F2C(O)Me
18026-chloro-1,2,4-triazin-5-yl2.5-F2C(O)Me
18036-bromo-1,2,4-triazin-5-yl2.5-F2C(O)Me
18043,6-difluoro-1,2,4-triazin-5-yl2.5-F2C(O)Me
18056-chloro-3-fluoro-1,2,4-triazin-5-yl2.5-F2C(O)Me
18066-bromo-3-fluoro-1,2,4-triazin-5-yl2.5-F2C(O)Me
18073-chloro-6-fluoro-1,2,4-triazin-5-yl2.5-F2C(O)Me
18083-bromo-6-fluoro-1,2,4-triazin-5-yl2.5-F2C(O)Me
18091,2,4-triazin-3-yl2.5-F2C(O)Me
18106-fluoro-1,2,4-triazin-3-yl2.5-F2C(O)Me
18116-chloro-1,2,4-triazin-3-yl2.5-F2C(O)Me
18126-bromo-1,2,4-triazin-3-yl2.5-F2C(O)Me
18135-fluoro-1,2,4-triazin-3-yl2.5-F2C(O)Me
18145-chloro-1,2,4-triazin-3-yl2.5-F2C(O)Me
18155-bromo-1,2,4-triazin-3-yl2.5-F2C(O)Me
18165-chloro-6-fluoro-1,2,4-triazin-3-yl2.5-F2C(O)Me
18175-bromo-6-fluoro-1,2,4-triazin-3-yl2.5-F2C(O)Me
18185,6-difluoro-1,2,4-triazin-3-yl2.5-F2C(O)Me
18196-chloro-5-fluoro-1,2,4-triazin-3-yl2.5-F2C(O)Me
18206-bromo-5-fluoro-1,2,4-triazin-3-yl2.5-F2C(O)Me
18211,2,4-triazin-6-yl2.5-F2C(O)Me
18223-fluoro-1,2,4-triazin-6-yl2.5-F2C(O)Me
18233-chloro-1,2,4-triazin-6-yl2.5-F2C(O)Me
18243-bromo-1,2,4-triazin-6-yl2.5-F2C(O)Me
18255-fluoro-1,2,4-triazin-6-yl2.5-F2C(O)Me
18265-chloro-1,2,4-triazin-6-yl2.5-F2C(O)Me
18275-bromo-1,2,4-triazin-6-yl2.5-F2C(O)Me
18283,5-difluoro-1,2,4-triazin-6-yl2.5-F2C(O)Me
18295-chloro-3-fluoro-1,2,4-triazin-6-yl2.5-F2C(O)Me
18305-bromo-3-fluoro-1,2,4-triazin-6-yl2.5-F2C(O)Me
18313-chloro-5-fluoro-1,2,4-triazin-6-yl2.5-F2C(O)Me

[0000]

Preferred meanings of Q(R2)n, (R3)mand R1in
compounds of the formula (I) according to the invention
No.Q(R2)n(R3)mR1
18326-fluoropyridin-3-yl2.3-F2H
18336-chloropyridin-3-yl2.3-F2H
18346-bromopyridin-3-yl2.3-F2H
18355-fluoropyridin-3-yl2.3-F2H
18365-chloropyridin-3-yl2.3-F2H
18375-bromopyridin-3-yl2.3-F2H
18384-fluoropyridin-3-yl2.3-F2H
18394-chloropyridin-3-yl2.3-F2H
18404-bromopyridin-3-yl2.3-F2H
18412-fluoropyridin-3-yl2.3-F2H
18422-chloropyridin-3-yl2.3-F2H
18432-bromopyridin-3-yl2.3-F2H
18442,6-difluoropyridin-3-yl2.3-F2H
18455-chloro-6-fluoropyridin-3-yl2.3-F2H
18465-bromo-6-fluoropyridin-3-yl2.3-F2H
18475,6-difluoropyridin-3-yl2.3-F2H
18486-chloro-5-fluoropyridin-3-yl2.3-F2H
18496-bromo-5-fluoropyridin-3-yl2.3-F2H
18504,5-difluoropyridin-3-yl2.3-F2H
18514-chloro-5-fluoropyridin-3-yl2.3-F2H
18524-bromo-5-fluoropyridin-3-yl2.3-F2H
18535-chloro-4-fluoropyridin-3-yl2.3-F2H
18544,5-dichloropyridin-3-yl2.3-F2H
18554-bromo-5-chloropyridin-3-yl2.3-F2H
18565-bromo-4-fluoropyridin-3-yl2.3-F2H
18575-bromo-4-chloropyridin-3-yl2.3-F2H
18584,5-dibromopyridin-3-yl2.3-F2H
18592,5,6-trifluoropyridin-3-yl2.3-F2H
18602-chloro-5,6-difluoropyridin-3-yl2.3-F2H
18612-bromo-5,6-difluoropyridin-3-yl2.3-F2H
18626-chloro-2,5-difluoropyridin-3-yl2.3-F2H
18636-bromo-2,5-difluoropyridin-3-yl2.3-F2H
18645-chloro-2,6-difluoropyridin-3-yl2.3-F2H
18655-bromo-2,6-difluoropyridin-3-yl2.3-F2H
18664,5,6-trifluoropyridin-3-yl2.3-F2H
18674-chloro-5,6-difluoropyridin-3-yl2.3-F2H
18684-bromo-5,6-difluoropyridin-3-yl2.3-F2H
18695-chloro-4,6-difluoropyridin-3-yl2.3-F2H
18705-bromo-4,6-difluoropyridin-3-yl2.3-F2H
18716-chloro-4,5-difluoropyridin-3-yl2.3-F2H
18726-bromo-4,5-difluoropyridin-3-yl2.3-F2H
1873pyridin-3-yl2.3-F2H
18746-fluoropyridin-3-yl2.6-F2.4-ClH
18756-chloropyridin-3-yl2.6-F2.4-ClH
18766-bromopyridin-3-yl2.6-F2.4-ClH
18775-fluoropyridin-3-yl2.6-F2.4-ClH
18785-chloropyridin-3-yl2.6-F2.4-ClH
18795-bromopyridin-3-yl2.6-F2.4-ClH
18804-fluoropyridin-3-yl2.6-F2.4-ClH
18814-chloropyridin-3-yl2.6-F2.4-ClH
18824-bromopyridin-3-yl2.6-F2.4-ClH
18832-fluoropyridin-3-yl2.6-F2.4-ClH
18842-chloropyridin-3-yl2.6-F2.4-ClH
18852-bromopyridin-3-yl2.6-F2.4-ClH
18862,6-difluoropyridin-3-yl2.6-F2.4-ClH
18875-chloro-6-fluoropyridin-3-yl2.6-F2.4-ClH
18885-bromo-6-fluoropyridin-3-yl2.6-F2.4-ClH
18895,6-difluoropyridin-3-yl2.6-F2.4-ClH
18906-chloro-5-fluoropyridin-3-yl2.6-F2.4-ClH
18916-bromo-5-fluoropyridin-3-yl2.6-F2.4-ClH
18924,5-difluoropyridin-3-yl2.6-F2.4-ClH
18934-chloro-5-fluoropyridin-3-yl2.6-F2.4-ClH
18944-bromo-5-fluoropyridin-3-yl2.6-F2.4-ClH
18955-chloro-4-fluoropyridin-3-yl2.6-F2.4-ClH
18964,5-dichloropyridin-3-yl2.6-F2.4-ClH
18974-bromo-5-chloropyridin-3-yl2.6-F2.4-ClH
18985-bromo-4-fluoropyridin-3-yl2.6-F2.4-ClH
18995-bromo-4-chloropyridin-3-yl2.6-F2.4-ClH
19004,5-dibromopyridin-3-yl2.6-F2.4-ClH
19012,5,6-trifluoropyridin-3-yl2.6-F2.4-ClH
19022-chloro-5,6-difluoropyridin-3-yl2.6-F2.4-ClH
19032-bromo-5,6-difluoropyridin-3-yl2.6-F2.4-ClH
19046-chloro-2,5-difluoropyridin-3-yl2.6-F2.4-ClH
19056-bromo-2, 5-difluoropyridin-3-yl2.6-F2.4-ClH
19065-chloro-2,6-difluoropyridin-3-yl2.6-F2.4-ClH
19075-bromo-2,6-difluoropyridin-3-yl2.6-F2.4-ClH
19084,5,6-trifluoropyridin-3-yl2.6-F2.4-ClH
19094-chloro-5,6-difluoropyridin-3-yl2.6-F2.4-ClH
19104-bromo-5,6-difluoropyridin-3-yl2.6-F2.4-ClH
19115-chloro-4,6-difluoropyridin-3-yl2.6-F2.4-ClH
19125-bromo-4,6-difluoropyridin-3-yl2.6-F2.4-ClH
19136-chloro-4,5-difluoropyridin-3-yl2.6-F2.4-ClH
19146-bromo-4,5-difluoropyridin-3-yl2.6-F2.4-ClH
1915pyridin-3-yl2.6-F2.4-ClH
1916pyridin-2-yl2.6-F2.4-ClH
1917pyridin-4-yl2.6-F2.4-ClH
19186-fluoropyridin-3-yl2.4,6-F3H
19196-chloropyridin-3-yl2.4,6-F3H
19206-bromopyridin-3-yl2.4,6-F3H
19215-fluoropyridin-3-yl2.4,6-F3H
19225-chloropyridin-3-yl2.4,6-F3H
19235-bromopyridin-3-yl2.4,6-F3H
19244-fluoropyridin-3-yl2.4,6-F3H
19254-chloropyridin-3-yl2.4,6-F3H
19264-bromopyridin-3-yl2.4,6-F3H
19272-fluoropyridin-3-yl2.4,6-F3H
19282-chloropyridin-3-yl2.4,6-F3H
19292-bromopyridin-3-yl2.4,6-F3H
19302,6-difluoropyridin-3-yl2.4,6-F3H
19315-chloro-6-fluoropyridin-3-yl2.4,6-F3H
19325-bromo-6-fluoropyridin-3-yl2.4,6-F3H
19335,6-difluoropyridin-3-yl2.4,6-F3H
19346-chloro-5-fluoropyridin-3-yl2.4,6-F3H
19356-bromo-5-fluoropyridin-3-yl2.4,6-F3H
19364,5-difluoropyridin-3-yl2.4,6-F3H
19374-chloro-5-fluoropyridin-3-yl2.4,6-F3H
19384-bromo-5-fluoropyridin-3-yl2.4,6-F3H
19395-chloro-4-fluoropyridin-3-yl2.4,6-F3H
19404,5-dichloropyridin-3-yl2.4,6-F3H
19414-bromo-5-chloropyridin-3-yl2.4,6-F3H
19425-bromo-4-fluoropyridin-3-yl2.4,6-F3H
19435-bromo-4-chloropyridin-3-yl2.4,6-F3H
19444,5-dibromopyridin-3-yl2.4,6-F3H
19452,5,6-trifluoropyridin-3-yl2.4,6-F3H
19462-chloro-5,6-difluoropyridin-3-yl2.4,6-F3H
19472-bromo-5,6-difluoropyridin-3-yl2.4,6-F3H
19486-chloro-2,5-difluoropyridin-3-yl2.4,6-F3H
19496-bromo-2, 5-difluoropyridin-3-yl2.4,6-F3H
19505-chloro-2,6-difluoropyridin-3-yl2.4,6-F3H
19515-bromo-2,6-difluoropyridin-3-yl2.4,6-F3H
19524,5,6-trifluoropyridin-3-yl2.4,6-F3H
19534-chloro-5,6-difluoropyridin-3-yl2.4,6-F3H
19544-bromo-5,6-difluoropyridin-3-yl2.4,6-F3H
19555-chloro-4,6-difluoropyridin-3-yl2.4,6-F3H
19565-bromo-4,6-difluoropyridin-3-yl2.4,6-F3H
19576-chloro-4,5-difluoropyridin-3-yl2.4,6-F3H
19586-bromo-4,5-difluoropyridin-3-yl2.4,6-F3H
1959pyridin-3-yl2.4,6-F3H
19606-fluoropyridin-3-yl2-FH
19616-chloropyridin-3-yl2-FH
19626-bromopyridin-3-yl2-FH
19635-fluoropyridin-3-yl2-FH
19645-chloropyridin-3-yl2-FH
19655-bromopyridin-3-yl2-FH
19664-fluoropyridin-3-yl2-FH
19674-chloropyridin-3-yl2-FH
19684-bromopyridin-3-yl2-FH
19692-fluoropyridin-3-yl2-FH
19702-chloropyridin-3-yl2-FH
19712-bromopyridin-3-yl2-FH
19722,6-difluoropyridin-3-yl2-FH
19735-chloro-6-fluoropyridin-3-yl2-FH
19745-bromo-6-fluoropyridin-3-yl2-FH
19755,6-difluoropyridin-3-yl2-FH
19766-chloro-5-fluoropyridin-3-yl2-FH
19776-bromo-5-fluoropyridin-3-yl2-FH
19784,5-difluoropyridin-3-yl2-FH
19794-chloro-5-fluoropyridin-3-yl2-FH
19804-bromo-5-fluoropyridin-3-yl2-FH
19815-chloro-4-fluoropyridin-3-yl2-FH
19824,5-dichloropyridin-3-yl2-FH
19834-bromo-5-chloropyridin-3-yl2-FH
19845-bromo-4-fluoropyridin-3-yl2-FH
19855-bromo-4-chloropyridin-3-yl2-FH
19864,5-dibromopyridin-3-yl2-FH
19872,5,6-trifluoropyridin-3-yl2-FH
19882-chloro-5,6-difluoropyridin-3-yl2-FH
19892-bromo-5,6-difluoropyridin-3-yl2-FH
19906-chloro-2,5-difluoropyridin-3-yl2-FH
19916-bromo-2, 5-difluoropyridin-3-yl2-FH
19925-chloro-2,6-difluoropyridin-3-yl2-FH
19935-bromo-2,6-difluoropyridin-3-yl2-FH
19944,5,6-trifluoropyridin-3-yl2-FH
19954-chloro-5,6-difluoropyridin-3-yl2-FH
19964-bromo-5,6-difluoropyridin-3-yl2-FH
19975-chloro-4,6-difluoropyridin-3-yl2-FH
19985-bromo-4,6-difluoropyridin-3-yl2-FH
19996-chloro-4,5-difluoropyridin-3-yl2-FH
20006-bromo-4,5-difluoropyridin-3-yl2-FH
2001pyridin-3-yl2-FH
20026-fluoropyridin-3-yl2.3,6-F3H
20036-chloropyridin-3-yl2.3,6-F3H
20046-bromopyridin-3-yl2.3,6-F3H
20055-fluoropyridin-3-yl2.3,6-F3H
20065-chloropyridin-3-yl2.3,6-F3H
20075-bromopyridin-3-yl2.3,6-F3H
20084-fluoropyridin-3-yl2.3,6-F3H
20094-chloropyridin-3-yl2.3,6-F3H
20104-bromopyridin-3-yl2.3,6-F3H
20112-fluoropyridin-3-yl2.3,6-F3H
20122-chloropyridin-3-yl2.3,6-F3H
20132-bromopyridin-3-yl2.3,6-F3H
20142,6-difluoropyridin-3-yl2.3,6-F3H
20155-chloro-6-fluoropyridin-3-yl2.3,6-F3H
20165-bromo-6-fluoropyridin-3-yl2.3,6-F3H
20175,6-difluoropyridin-3-yl2.3,6-F3H
20186-chloro-5-fluoropyridin-3-yl2.3,6-F3H
20196-bromo-5-fluoropyridin-3-yl2.3,6-F3H
20204,5-difluoropyridin-3-yl2.3,6-F3H
20214-chloro-5-fluoropyridin-3-yl2.3,6-F3H
20224-bromo-5-fluoropyridin-3-yl2.3,6-F3H
20235-chloro-4-fluoropyridin-3-yl2.3,6-F3H
20244,5-dichloropyridin-3-yl2.3,6-F3H
20254-bromo-5-chloropyridin-3-yl2.3,6-F3H
20265-bromo-4-fluoropyridin-3-yl2.3,6-F3H
20275-bromo-4-chloropyridin-3-yl2.3,6-F3H
20284,5-dibromopyridin-3-yl2.3,6-F3H
20292,5,6-trifluoropyridin-3-yl2.3,6-F3H
20302-chloro-5,6-difluoropyridin-3-yl2.3,6-F3H
20312-bromo-5,6-difluoropyridin-3-yl2.3,6-F3H
20326-chloro-2,5-difluoropyridin-3-yl2.3,6-F3H
20336-bromo-2,5-difluoropyridin-3-yl2.3,6-F3H
20345-chloro-2,6-difluoropyridin-3-yl2.3,6-F3H
20355-bromo-2,6-difluoropyridin-3-yl2.3,6-F3H
20364,5,6-trifluoropyridin-3-yl2.3,6-F3H
20374-chloro-5,6-difluoropyridin-3-yl2.3,6-F3H
20384-bromo-5,6-difluoropyridin-3-yl2.3,6-F3H
20395-chloro-4,6-difluoropyridin-3-yl2.3,6-F3H
20405-bromo-4,6-difluoropyridin-3-yl2.3,6-F3H
20416-chloro-4,5-difluoropyridin-3-yl2.3,6-F3H
20426-bromo-4,5-difluoropyridin-3-yl2.3,6-F3H
2043pyridin-3-yl2.3,6-F3H
20446-fluoropyridin-3-yl3-NO2H
20456-chloropyridin-3-yl3-NO2H
20466-bromopyridin-3-yl3-NO2H
20475-fluoropyridin-3-yl3-NO2H
20485-chloropyridin-3-yl3-NO2H
20495-bromopyridin-3-yl3-NO2H
20504-fluoropyridin-3-yl3-NO2H
20514-chloropyridin-3-yl3-NO2H
20524-bromopyridin-3-yl3-NO2H
20532-fluoropyridin-3-yl3-NO2H
20542-chloropyridin-3-yl3-NO2H
20552-bromopyridin-3-yl3-NO2H
20562,6-difluoropyridin-3-yl3-NO2H
20575-chloro-6-fluoropyridin-3-yl3-NO2H
20585-bromo-6-fluoropyridin-3-yl3-NO2H
20595,6-difluoropyridin-3-yl3-NO2H
20606-chloro-5-fluoropyridin-3-yl3-NO2H
20616-bromo-5-fluoropyridin-3-yl3-NO2H
20624,5-difluoropyridin-3-yl3-NO2H
20634-chloro-5-fluoropyridin-3-yl3-NO2H
20644-bromo-5-fluoropyridin-3-yl3-NO2H
20655-chloro-4-fluoropyridin-3-yl3-NO2H
20664,5-dichloropyridin-3-yl3-NO2H
20674-bromo-5-chloropyridin-3-yl3-NO2H
20685-bromo-4-fluoropyridin-3-yl3-NO2H
20695-bromo-4-chloropyridin-3-yl3-NO2H
20704,5-dibromopyridin-3-yl3-NO2H
20712,5,6-trifluoropyridin-3-yl3-NO2H
20722-chloro-5,6-difluoropyridin-3-yl3-NO2H
20732-bromo-5,6-difluoropyridin-3-yl3-NO2H
20746-chloro-2,5-difluoropyridin-3-yl3-NO2H
20756-bromo-2,5-difluoropyridin-3-yl3-NO2H
20765-chloro-2,6-difluoropyridin-3-yl3-NO2H
20775-bromo-2,6-difluoropyridin-3-yl3-NO2H
20784,5,6-trifluoropyridin-3-yl3-NO2H
20794-chloro-5,6-difluoropyridin-3-yl3-NO2H
20804-bromo-5,6-difluoropyridin-3-yl3-NO2H
20815-chloro-4,6-difluoropyridin-3-yl3-NO2H
20825-bromo-4,6-difluoropyridin-3-yl3-NO2H
20836-chloro-4,5-difluoropyridin-3-yl3-NO2H
20846-bromo-4,5-difluoropyridin-3-yl3-NO2H
2085pyridin-3-yl3-NO2H
20866-fluoropyridin-3-yl4-NO2H
20876-chloropyridin-3-yl4-NO2H
20886-bromopyridin-3-yl4-NO2H
20895-fluoropyridin-3-yl4-NO2H
20905-chloropyridin-3-yl4-NO2H
20915-bromopyridin-3-yl4-NO2H
20924-fluoropyridin-3-yl4-NO2H
20934-chloropyridin-3-yl4-NO2H
20944-bromopyridin-3-yl4-NO2H
20952-fluoropyridin-3-yl4-NO2H
20962-chloropyridin-3-yl4-NO2H
20972-bromopyridin-3-yl4-NO2H
20982,6-difluoropyridin-3-yl4-NO2H
20995-chloro-6-fluoropyridin-3-yl4-NO2H
21005-bromo-6-fluoropyridin-3-yl4-NO2H
21015,6-difluoropyridin-3-yl4-NO2H
21026-chloro-5-fluoropyridin-3-yl4-NO2H
21036-bromo-5-fluoropyridin-3-yl4-NO2H
21044,5-difluoropyridin-3-yl4-NO2H
21054-chloro-5-fluoropyridin-3-yl4-NO2H
21064-bromo-5-fluoropyridin-3-yl4-NO2H
21075-chloro-4-fluoropyridin-3-yl4-NO2H
21084,5-dichloropyridin-3-yl4-NO2H
21094-bromo-5-chloropyridin-3-yl4-NO2H
21105-bromo-4-fluoropyridin-3-yl4-NO2H
21115-bromo-4-chloropyridin-3-yl4-NO2H
21124,5-dibromopyridin-3-yl4-NO2H
21132,5,6-trifluoropyridin-3-yl4-NO2H
21142-chloro-5,6-difluoropyridin-3-yl4-NO2H
21152-bromo-5,6-difluoropyridin-3-yl4-NO2H
21166-chloro-2,5-difluoropyridin-3-yl4-NO2H
21176-bromo-2,5-difluoropyridin-3-yl4-NO2H
21185-chloro-2,6-difluoropyridin-3-yl4-NO2H
21195-bromo-2,6-difluoropyridin-3-yl4-NO2H
21204,5,6-trifluoropyridin-3-yl4-NO2H
21214-chloro-5,6-difluoropyridin-3-yl4-NO2H
21224-bromo-5,6-difluoropyridin-3-yl4-NO2H
21235-chloro-4,6-difluoropyridin-3-yl4-NO2H
21245-bromo-4,6-difluoropyridin-3-yl4-NO2H
21256-chloro-4,5-difluoropyridin-3-yl4-NO2H
21266-bromo-4,5-difluoropyridin-3-yl4-NO2H
2127pyridin-3-yl4-NO2H
21286-fluoropyridin-3-yl4-OMeH
21296-chloropyridin-3-yl4-OMeH
21306-bromopyridin-3-yl4-OMeH
21315-fluoropyridin-3-yl4-OMeH
21325-chloropyridin-3-yl4-OMeH
21335-bromopyridin-3-yl4-OMeH
21344-fluoropyridin-3-yl4-OMeH
21354-chloropyridin-3-yl4-OMeH
21364-bromopyridin-3-yl4-OMeH
21372-fluoropyridin-3-yl4-OMeH
21382-chloropyridin-3-yl4-OMeH
21392-bromopyridin-3-yl4-OMeH
21402,6-difluoropyridin-3-yl4-OMeH
21415-chloro-6-fluoropyridin-3-yl4-OMeH
21425-bromo-6-fluoropyridin-3-yl4-OMeH
21435,6-difluoropyridin-3-yl4-OMeH
21446-chloro-5-fluoropyridin-3-yl4-OMeH
21456-bromo-5-fluoropyridin-3-yl4-OMeH
21464,5-difluoropyridin-3-yl4-OMeH
21474-chloro-5-fluoropyridin-3-yl4-OMeH
21484-bromo-5-fluoropyridin-3-yl4-OMeH
21495-chloro-4-fluoropyridin-3-yl4-OMeH
21504,5-dichloropyridin-3-yl4-OMeH
21514-bromo-5-chloropyridin-3-yl4-OMeH
21525-bromo-4-fluoropyridin-3-yl4-OMeH
21535-bromo-4-chloropyridin-3-yl4-OMeH
21544,5-dibromopyridin-3-yl4-OMeH
21552,5,6-trifluoropyridin-3-yl4-OMeH
21562-chloro-5,6-difluoropyridin-3-yl4-OMeH
21572-bromo-5,6-difluoropyridin-3-yl4-OMeH
21586-chloro-2,5-difluoropyridin-3-yl4-OMeH
21596-bromo-2,5-difluoropyridin-3-yl4-OMeH
21605-chloro-2,6-difluoropyridin-3-yl4-OMeH
21615-bromo-2,6-difluoropyridin-3-yl4-OMeH
21624,5,6-trifluoropyridin-3-yl4-OMeH
21634-chloro-5,6-difluoropyridin-3-yl4-OMeH
21644-bromo-5,6-difluoropyridin-3-yl4-OMeH
21655-chloro-4,6-difluoropyridin-3-yl4-OMeH
21665-bromo-4,6-difluoropyridin-3-yl4-OMeH
21676-chloro-4,5-difluoropyridin-3-yl4-OMeH
21686-bromo-4,5-difluoropyridin-3-yl4-OMeH
2169pyridin-3-yl4-OMeH
2170pyridin-2-yl4-OMeH
2171pyridin-4-yl4-OMeH
21726-fluoropyridin-3-yl4-CF3H
21736-chloropyridin-3-yl4-CF3H
21746-bromopyridin-3-yl4-CF3H
21755-fluoropyridin-3-yl4-CF3H
21765-chloropyridin-3-yl4-CF3H
21775-bromopyridin-3-yl4-CF3H
21784-fluoropyridin-3-yl4-CF3H
21794-chloropyridin-3-yl4-CF3H
21804-bromopyridin-3-yl4-CF3H
21812-fluoropyridin-3-yl4-CF3H
21822-chloropyridin-3-yl4-CF3H
21832-bromopyridin-3-yl4-CF3H
21842,6-difluoropyridin-3-yl4-CF3H
21855-chloro-6-fluoropyridin-3-yl4-CF3H
21865-bromo-6-fluoropyridin-3-yl4-CF3H
21875,6-difluoropyridin-3-yl4-CF3H
21886-chloro-5-fluoropyridin-3-yl4-CF3H
21896-bromo-5-fluoropyridin-3-yl4-CF3H
21904,5-difluoropyridin-3-yl4-CF3H
21914-chloro-5-fluoropyridin-3-yl4-CF3H
21924-bromo-5-fluoropyridin-3-yl4-CF3H
21935-chloro-4-fluoropyridin-3-yl4-CF3H
21944,5-dichloropyridin-3-yl4-CF3H
21954-bromo-5-chloropyridin-3-yl4-CF3H
21965-bromo-4-fluoropyridin-3-yl4-CF3H
21975-bromo-4-chloropyridin-3-yl4-CF3H
21984,5-dibromopyridin-3-yl4-CF3H
21992,5,6-trifluoropyridin-3-yl4-CF3H
22002-chloro-5,6-difluoropyridin-3-yl4-CF3H
22012-bromo-5,6-difluoropyridin-3-yl4-CF3H
22026-chloro-2,5-difluoropyridin-3-yl4-CF3H
22036-bromo-2,5-difluoropyridin-3-yl4-CF3H
22045-chloro-2,6-difluoropyridin-3-yl4-CF3H
22055-bromo-2,6-difluoropyridin-3-yl4-CF3H
22064,5,6-trifluoropyridin-3-yl4-CF3H
22074-chloro-5,6-difluoropyridin-3-yl4-CF3H
22084-bromo-5,6-difluoropyridin-3-yl4-CF3H
22095-chloro-4,6-difluoropyridin-3-yl4-CF3H
22105-bromo-4,6-difluoropyridin-3-yl4-CF3H
22116-chloro-4,5-difluoropyridin-3-yl4-CF3H
22126-bromo-4,5-difluoropyridin-3-yl4-CF3H
2213pyridin-3-yl4-CF3H
22146-fluoropyridin-3-yl4-ClH
22156-chloropyridin-3-yl4-ClH
22166-bromopyridin-3-yl4-ClH
22175-fluoropyridin-3-yl4-ClH
22185-chloropyridin-3-yl4-ClH
22195-bromopyridin-3-yl4-ClH
22204-fluoropyridin-3-yl4-ClH
22214-chloropyridin-3-yl4-ClH
22224-bromopyridin-3-yl4-ClH
22232-fluoropyridin-3-yl4-ClH
22242-chloropyridin-3-yl4-ClH
22252-bromopyridin-3-yl4-ClH
22262,6-difluoropyridin-3-yl4-ClH
22275-chloro-6-fluoropyridin-3-yl4-ClH
22285-bromo-6-fluoropyridin-3-yl4-ClH
22295,6-difluoropyridin-3-yl4-ClH
22306-chloro-5-fluoropyridin-3-yl4-ClH
22316-bromo-5-fluoropyridin-3-yl4-ClH
22324,5-difluoropyridin-3-yl4-ClH
22334-chloro-5-fluoropyridin-3-yl4-ClH
22344-bromo-5-fluoropyridin-3-yl4-ClH
22355-chloro-4-fluoropyridin-3-yl4-ClH
22364,5-dichloropyridin-3-yl4-ClH
22374-bromo-5-chloropyridin-3-yl4-ClH
22385-bromo-4-fluoropyridin-3-yl4-ClH
22395-bromo-4-chloropyridin-3-yl4-ClH
22404,5-dibromopyridin-3-yl4-ClH
22412,5,6-trifluoropyridin-3-yl4-ClH
22422-chloro-5,6-difluoropyridin-3-yl4-ClH
22432-bromo-5,6-difluoropyridin-3-yl4-ClH
22446-chloro-2,5-difluoropyridin-3-yl4-ClH
22456-bromo-2,5-difluoropyridin-3-yl4-ClH
22465-chloro-2,6-difluoropyridin-3-yl4-ClH
22475-bromo-2,6-difluoropyridin-3-yl4-ClH
22485-chloro-3,6-difluoropyridin-2-yl4-ClH
22495-bromo-3,6-difluoropyridin-2-yl4-ClH
22504,5,6-trifluoropyridin-3-yl4-ClH
22514-chloro-5,6-difluoropyridin-3-yl4-ClH
22524-bromo-5,6-difluoropyridin-3-yl4-ClH
22535-chloro-4,6-difluoropyridin-3-yl4-ClH
22545-bromo-4,6-difluoropyridin-3-yl4-ClH
22556-chloro-4,5-difluoropyridin-3-yl4-ClH
22566-bromo-4,5-difluoropyridin-3-yl4-ClH
2257pyridin-3-yl4-ClH
22586-fluoropyridin-3-yl4-FH
22596-chloropyridin-3-yl4-FH
22606-bromopyridin-3-yl4-FH
22615-fluoropyridin-3-yl4-FH
22625-chloropyridin-3-yl4-FH
22635-bromopyridin-3-yl4-FH
22644-fluoropyridin-3-yl4-FH
22654-chloropyridin-3-yl4-FH
22664-bromopyridin-3-yl4-FH
22672-fluoropyridin-3-yl4-FH
22682-chloropyridin-3-yl4-FH
22692-bromopyridin-3-yl4-FH
22702,6-difluoropyridin-3-yl4-FH
22715-chloro-6-fluoropyridin-3-yl4-FH
22725-bromo-6-fluoropyridin-3-yl4-FH
22735,6-difluoropyridin-3-yl4-FH
22746-chloro-5-fluoropyridin-3-yl4-FH
22756-bromo-5-fluoropyridin-3-yl4-FH
22764,5-difluoropyridin-3-yl4-FH
22774-chloro-5-fluoropyridin-3-yl4-FH
22784-bromo-5-fluoropyridin-3-yl4-FH
22795-chloro-4-fluoropyridin-3-yl4-FH
22804,5-dichloropyridin-3-yl4-FH
22814-bromo-5-chloropyridin-3-yl4-FH
22825-bromo-4-fluoropyridin-3-yl4-FH
22835-bromo-4-chloropyridin-3-yl4-FH
22844,5-dibromopyridin-3-yl4-FH
22852,5,6-trifluoropyridin-3-yl4-FH
22862-chloro-5,6-difluoropyridin-3-yl4-FH
22872-bromo-5,6-difluoropyridin-3-yl4-FH
22886-chloro-2,5-difluoropyridin-3-yl4-FH
22896-bromo-2,5-difluoropyridin-3-yl4-FH
22905-chloro-2,6-difluoropyridin-3-yl4-FH
22915-bromo-2,6-difluoropyridin-3-yl4-FH
22924,5,6-trifluoropyridin-3-yl4-FH
22934-chloro-5,6-difluoropyridin-3-yl4-FH
22944-bromo-5,6-difluoropyridin-3-yl4-FH
22955-chloro-4,6-difluoropyridin-3-yl4-FH
22965-bromo-4,6-difluoropyridin-3-yl4-FH
22976-chloro-4,5-difluoropyridin-3-yl4-FH
22986-bromo-4,5-difluoropyridin-3-yl4-FH
2299pyridin-3-yl4-FH
23006-fluoropyridin-3-yl3-OCF3H
23016-chloropyridin-3-yl3-OCF3H
23026-bromopyridin-3-yl3-OCF3H
23035-fluoropyridin-3-yl3-OCF3H
23045-chloropyridin-3-yl3-OCF3H
23055-bromopyridin-3-yl3-OCF3H
23064-fluoropyridin-3-yl3-OCF3H
23074-chloropyridin-3-yl3-OCF3H
23084-bromopyridin-3-yl3-OCF3H
23092-fluoropyridin-3-yl3-OCF3H
23102-chloropyridin-3-yl3-OCF3H
23112-bromopyridin-3-yl3-OCF3H
23122,6-difluoropyridin-3-yl3-OCF3H
23135-chloro-6-fluoropyridin-3-yl3-OCF3H
23145-bromo-6-fluoropyridin-3-yl3-OCF3H
23155,6-difluoropyridin-3-yl3-OCF3H
23166-chloro-5-fluoropyridin-3-yl3-OCF3H
23176-bromo-5-fluoropyridin-3-yl3-OCF3H
23184,5-difluoropyridin-3-yl3-OCF3H
23194-chloro-5-fluoropyridin-3-yl3-OCF3H
23204-bromo-5-fluoropyridin-3-yl3-OCF3H
23215-chloro-4-fluoropyridin-3-yl3-OCF3H
23224,5-dichloropyridin-3-yl3-OCF3H
23234-bromo-5-chloropyridin-3-yl3-OCF3H
23245-bromo-4-fluoropyridin-3-yl3-OCF3H
23255-bromo-4-chloropyridin-3-yl3-OCF3H
23264,5-dibromopyridin-3-yl3-OCF3H
23272,5,6-trifluoropyridin-3-yl3-OCF3H
23282-chloro-5,6-difluoropyridin-3-yl3-OCF3H
23292-bromo-5,6-difluoropyridin-3-yl3-OCF3H
23306-chloro-2,5-difluoropyridin-3-yl3-OCF3H
23316-bromo-2,5-difluoropyridin-3-yl3-OCF3H
23325-chloro-2,6-difluoropyridin-3-yl3-OCF3H
23335-bromo-2,6-difluoropyridin-3-yl3-OCF3H
23344,5,6-trifluoropyridin-3-yl3-OCF3H
23354-chloro-5,6-difluoropyridin-3-yl3-OCF3H
23364-bromo-5,6-difluoropyridin-3-yl3-OCF3H
23375-chloro-4,6-difluoropyridin-3-yl3-OCF3H
23385-bromo-4,6-difluoropyridin-3-yl3-OCF3H
23396-chloro-4,5-difluoropyridin-3-yl3-OCF3H
23406-bromo-4,5-difluoropyridin-3-yl3-OCF3H
2341pyridin-3-yl3-OCF3H
23426-fluoropyridin-3-yl4-OCF3H
23436-chloropyridin-3-yl4-OCF3H
23446-bromopyridin-3-yl4-OCF3H
23455-fluoropyridin-3-yl4-OCF3H
23465-chloropyridin-3-yl4-OCF3H
23475-bromopyridin-3-yl4-OCF3H
23484-fluoropyridin-3-yl4-OCF3H
23494-chloropyridin-3-yl4-OCF3H
23504-bromopyridin-3-yl4-OCF3H
23512-fluoropyridin-3-yl4-OCF3H
23522-chloropyridin-3-yl4-OCF3H
23532-bromopyridin-3-yl4-OCF3H
23542,6-difluoropyridin-3-yl4-OCF3H
23555-chloro-6-fluoropyridin-3-yl4-OCF3H
23565-bromo-6-fluoropyridin-3-yl4-OCF3H
23575,6-difluoropyridin-3-yl4-OCF3H
23586-chloro-5-fluoropyridin-3-yl4-OCF3H
23596-bromo-5-fluoropyridin-3-yl4-OCF3H
23604,5-difluoropyridin-3-yl4-OCF3H
23614-chloro-5-fluoropyridin-3-yl4-OCF3H
23624-bromo-5-fluoropyridin-3-yl4-OCF3H
23635-chloro-4-fluoropyridin-3-yl4-OCF3H
23644,5-dichloropyridin-3-yl4-OCF3H
23654-bromo-5-chloropyridin-3-yl4-OCF3H
23665-bromo-4-fluoropyridin-3-yl4-OCF3H
23675-bromo-4-chloropyridin-3-yl4-OCF3H
23684,5-dibromopyridin-3-yl4-OCF3H
23692,5,6-trifluoropyridin-3-yl4-OCF3H
23702-chloro-5,6-difluoropyridin-3-yl4-OCF3H
23712-bromo-5,6-difluoropyridin-3-yl4-OCF3H
23726-chloro-2,5-difluoropyridin-3-yl4-OCF3H
23736-bromo-2,5-difluoropyridin-3-yl4-OCF3H
23745-chloro-2,6-difluoropyridin-3-yl4-OCF3H
23755-bromo-2,6-difluoropyridin-3-yl4-OCF3H
23764,5,6-trifluoropyridin-3-yl4-OCF3H
23774-chloro-5,6-difluoropyridin-3-yl4-OCF3H
23784-bromo-5,6-difluoropyridin-3-yl4-OCF3H
23795-chloro-4,6-difluoropyridin-3-yl4-OCF3H
23805-bromo-4,6-difluoropyridin-3-yl4-OCF3H
23816-chloro-4,5-difluoropyridin-3-yl4-OCF3H
23826-bromo-4,5-difluoropyridin-3-yl4-OCF3H
2383pyridin-3-yl4-OCF3H
23846-fluoropyridin-3-yl3-CNH
23856-chloropyridin-3-yl3-CNH
23866-bromopyridin-3-yl3-CNH
23875-fluoropyridin-3-yl3-CNH
23885-chloropyridin-3-yl3-CNH
23895-bromopyridin-3-yl3-CNH
23904-fluoropyridin-3-yl3-CNH
23914-chloropyridin-3-yl3-CNH
23924-bromopyridin-3-yl3-CNH
23932-fluoropyridin-3-yl3-CNH
23942-chloropyridin-3-yl3-CNH
23952-bromopyridin-3-yl3-CNH
23962,6-difluoropyridin-3-yl3-CNH
23975-chloro-6-fluoropyridin-3-yl3-CNH
23985-bromo-6-fluoropyridin-3-yl3-CNH
23995,6-difluoropyridin-3-yl3-CNH
24006-chloro-5-fluoropyridin-3-yl3-CNH
24016-bromo-5-fluoropyridin-3-yl3-CNH
24024,5-difluoropyridin-3-yl3-CNH
24034-chloro-5-fluoropyridin-3-yl3-CNH
24044-bromo-5-fluoropyridin-3-yl3-CNH
24055-chloro-4-fluoropyridin-3-yl3-CNH
24064,5-dichloropyridin-3-yl3-CNH
24074-bromo-5-chloropyridin-3-yl3-CNH
24085-bromo-4-fluoropyridin-3-yl3-CNH
24095-bromo-4-chloropyridin-3-yl3-CNH
24104,5-dibromopyridin-3-yl3-CNH
24112,5,6-trifluoropyridin-3-yl3-CNH
24122-chloro-5,6-difluoropyridin-3-yl3-CNH
24132-bromo-5,6-difluoropyridin-3-yl3-CNH
24146-chloro-2,5-difluoropyridin-3-yl3-CNH
24156-bromo-2,5-difluoropyridin-3-yl3-CNH
24165-chloro-2,6-difluoropyridin-3-yl3-CNH
24175-bromo-2,6-difluoropyridin-3-yl3-CNH
24184,5,6-trifluoropyridin-3-yl3-CNH
24194-chloro-5,6-difluoropyridin-3-yl3-CNH
24204-bromo-5,6-difluoropyridin-3-yl3-CNH
24215-chloro-4,6-difluoropyridin-3-yl3-CNH
24225-bromo-4,6-difluoropyridin-3-yl3-CNH
24236-chloro-4,5-difluoropyridin-3-yl3-CNH
24246-bromo-4,5-difluoropyridin-3-yl3-CNH
2425pyridin-3-yl3-CNH
24266-fluoropyridin-3-yl4-CNH
24276-chloropyridin-3-yl4-CNH
24286-bromopyridin-3-yl4-CNH
24295-fluoropyridin-3-yl4-CNH
24305-chloropyridin-3-yl4-CNH
24315-bromopyridin-3-yl4-CNH
24324-fluoropyridin-3-yl4-CNH
24334-chloropyridin-3-yl4-CNH
24344-bromopyridin-3-yl4-CNH
24352-fluoropyridin-3-yl4-CNH
24362-chloropyridin-3-yl4-CNH
24372-bromopyridin-3-yl4-CNH
24382,6-difluoropyridin-3-yl4-CNH
24395-chloro-6-fluoropyridin-3-yl4-CNH
24405-bromo-6-fluoropyridin-3-yl4-CNH
24415,6-difluoropyridin-3-yl4-CNH
24426-chloro-5-fluoropyridin-3-yl4-CNH
24436-bromo-5-fluoropyridin-3-yl4-CNH
24444,5-difluoropyridin-3-yl4-CNH
24454-chloro-5-fluoropyridin-3-yl4-CNH
24464-bromo-5-fluoropyridin-3-yl4-CNH
24475-chloro-4-fluoropyridin-3-yl4-CNH
24484,5-dichloropyridin-3-yl4-CNH
24494-bromo-5-chloropyridin-3-yl4-CNH
24505-bromo-4-fluoropyridin-3-yl4-CNH
24515-bromo-4-chloropyridin-3-yl4-CNH
24524,5-dibromopyridin-3-yl4-CNH
24532,5,6-trifluoropyridin-3-yl4-CNH
24542-chloro-5,6-difluoropyridin-3-yl4-CNH
24552-bromo-5,6-difluoropyridin-3-yl4-CNH
24566-chloro-2,5-difluoropyridin-3-yl4-CNH
24576-bromo-2,5-difluoropyridin-3-yl4-CNH
24585-chloro-2,6-difluoropyridin-3-yl4-CNH
24595-bromo-2,6-difluoropyridin-3-yl4-CNH
24604,5,6-trifluoropyridin-3-yl4-CNH
24614-chloro-5,6-difluoropyridin-3-yl4-CNH
24624-bromo-5,6-difluoropyridin-3-yl4-CNH
24635-chloro-4,6-difluoropyridin-3-yl4-CNH
24645-bromo-4,6-difluoropyridin-3-yl4-CNH
24656-chloro-4,5-difluoropyridin-3-yl4-CNH
24666-bromo-4,5-difluoropyridin-3-yl4-CNH
2467pyridin-3-yl4-CNH
2468pyridin-2-yl4-CNH
2469pyridin-4-yl4-CNH
24706-fluoropyridin-3-yl2.3-F2C(O)Me
24716-chloropyridin-3-yl2.3-F2C(O)Me
24726-bromopyridin-3-yl2.3-F2C(O)Me
24735-fluoropyridin-3-yl2.3-F2C(O)Me
24745-chloropyridin-3-yl2.3-F2C(O)Me
24755-bromopyridin-3-yl2.3-F2C(O)Me
24764-fluoropyridin-3-yl2.3-F2C(O)Me
24774-chloropyridin-3-yl2.3-F2C(O)Me
24784-bromopyridin-3-yl2.3-F2C(O)Me
24792-fluoropyridin-3-yl2.3-F2C(O)Me
24802-chloropyridin-3-yl2.3-F2C(O)Me
24812-bromopyridin-3-yl2.3-F2C(O)Me
24822,6-difluoropyridin-3-yl2.3-F2C(O)Me
24835-chloro-6-fluoropyridin-3-yl2.3-F2C(O)Me
24845-bromo-6-fluoropyridin-3-yl2.3-F2C(O)Me
24855,6-difluoropyridin-3-yl2.3-F2C(O)Me
24866-chloro-5-fluoropyridin-3-yl2.3-F2C(O)Me
24876-bromo-5-fluoropyridin-3-yl2.3-F2C(O)Me
24884,5-difluoropyridin-3-yl2.3-F2C(O)Me
24894-chloro-5-fluoropyridin-3-yl2.3-F2C(O)Me
24904-bromo-5-fluoropyridin-3-yl2.3-F2C(O)Me
24915-chloro-4-fluoropyridin-3-yl2.3-F2C(O)Me
24924,5-dichloropyridin-3-yl2.3-F2C(O)Me
24934-bromo-5-chloropyridin-3-yl2.3-F2C(O)Me
24945-bromo-4-fluoropyridin-3-yl2.3-F2C(O)Me
24955-bromo-4-chloropyridin-3-yl2.3-F2C(O)Me
24964,5-dibromopyridin-3-yl2.3-F2C(O)Me
24972,5,6-trifluoropyridin-3-yl2.3-F2C(O)Me
24982-chloro-5,6-difluoropyridin-3-yl2.3-F2C(O)Me
24992-bromo-5,6-difluoropyridin-3-yl2.3-F2C(O)Me
25006-chloro-2,5-difluoropyridin-3-yl2.3-F2C(O)Me
25016-bromo-2,5-difluoropyridin-3-yl2.3-F2C(O)Me
25025-chloro-2,6-difluoropyridin-3-yl2.3-F2C(O)Me
25035-bromo-2,6-difluoropyridin-3-yl2.3-F2C(O)Me
25044,5,6-trifluoropyridin-3-yl2.3-F2C(O)Me
25054-chloro-5,6-difluoropyridin-3-yl2.3-F2C(O)Me
25064-bromo-5,6-difluoropyridin-3-yl2.3-F2C(O)Me
25075-chloro-4,6-difluoropyridin-3-yl2.3-F2C(O)Me
25085-bromo-4,6-difluoropyridin-3-yl2.3-F2C(O)Me
25096-chloro-4,5-difluoropyridin-3-yl2.3-F2C(O)Me
25106-bromo-4,5-difluoropyridin-3-yl2.3-F2C(O)Me
2511pyridin-3-yl2.3-F2C(O)Me
25126-fluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25136-chloropyridin-3-yl2.6-F2.4-ClC(O)Me
25146-bromopyridin-3-yl2.6-F2.4-ClC(O)Me
25155-fluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25165-chloropyridin-3-yl2.6-F2.4-ClC(O)Me
25175-bromopyridin-3-yl2.6-F2.4-ClC(O)Me
25184-fluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25194-chloropyridin-3-yl2.6-F2.4-ClC(O)Me
25204-bromopyridin-3-yl2.6-F2.4-ClC(O)Me
25212-fluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25222-chloropyridin-3-yl2.6-F2.4-ClC(O)Me
25232-bromopyridin-3-yl2.6-F2.4-ClC(O)Me
25242,6-difluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25255-chloro-6-fluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25265-bromo-6-fluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25275,6-difluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25286-chloro-5-fluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25296-bromo-5-fluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25304,5-difluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25314-chloro-5-fluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25324-bromo-5-fluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25335-chloro-4-fluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25344,5-dichloropyridin-3-yl2.6-F2.4-ClC(O)Me
25354-bromo-5-chloropyridin-3-yl2.6-F2.4-ClC(O)Me
25365-bromo-4-fluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25375-bromo-4-chloropyridin-3-yl2.6-F2.4-ClC(O)Me
25384,5-dibromopyridin-3-yl2.6-F2.4-ClC(O)Me
25392,5,6-trifluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25402-chloro-5,6-difluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25412-bromo-5,6-difluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25426-chloro-2,5-difluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25436-bromo-2,5-difluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25445-chloro-2,6-difluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25455-bromo-2,6-difluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25464,5,6-trifluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25474-chloro-5,6-difluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25484-bromo-5,6-difluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25495-chloro-4,6-difluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25505-bromo-4,6-difluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25516-chloro-4,5-difluoropyridin-3-yl2.6-F2.4-ClC(O)Me
25526-bromo-4,5-difluoropyridin-3-yl2.6-F2.4-ClC(O)Me
2553pyridin-3-yl2.6-F2.4-ClC(O)Me
25546-fluoropyridin-3-yl2.4,6-F3C(O)Me
25556-chloropyridin-3-yl2.4,6-F3C(O)Me
25566-bromopyridin-3-yl2.4,6-F3C(O)Me
25575-fluoropyridin-3-yl2.4,6-F3C(O)Me
25585-chloropyridin-3-yl2.4,6-F3C(O)Me
25595-bromopyridin-3-yl2.4,6-F3C(O)Me
25604-fluoropyridin-3-yl2.4,6-F3C(O)Me
25614-chloropyridin-3-yl2.4,6-F3C(O)Me
25624-bromopyridin-3-yl2.4,6-F3C(O)Me
25632-fluoropyridin-3-yl2.4,6-F3C(O)Me
25642-chloropyridin-3-yl2.4,6-F3C(O)Me
25652-bromopyridin-3-yl2.4,6-F3C(O)Me
25662,6-difluoropyridin-3-yl2.4,6-F3C(O)Me
25675-chloro-6-fluoropyridin-3-yl2.4,6-F3C(O)Me
25685-bromo-6-fluoropyridin-3-yl2.4,6-F3C(O)Me
25695,6-difluoropyridin-3-yl2.4,6-F3C(O)Me
25706-chloro-5-fluoropyridin-3-yl2.4,6-F3C(O)Me
25716-bromo-5-fluoropyridin-3-yl2.4,6-F3C(O)Me
25724,5-difluoropyridin-3-yl2.4,6-F3C(O)Me
25734-chloro-5-fluoropyridin-3-yl2.4,6-F3C(O)Me
25744-bromo-5-fluoropyridin-3-yl2.4,6-F3C(O)Me
25755-chloro-4-fluoropyridin-3-yl2.4,6-F3C(O)Me
25764,5-dichloropyridin-3-yl2.4,6-F3C(O)Me
25774-bromo-5-chloropyridin-3-yl2.4,6-F3C(O)Me
25785-bromo-4-fluoropyridin-3-yl2.4,6-F3C(O)Me
25795-bromo-4-chloropyridin-3-yl2.4,6-F3C(O)Me
25804,5-dibromopyridin-3-yl2.4,6-F3C(O)Me
25812,5,6-trifluoropyridin-3-yl2.4,6-F3C(O)Me
25822-chloro-5,6-difluoropyridin-3-yl2.4,6-F3C(O)Me
25832-bromo-5,6-difluoropyridin-3-yl2.4,6-F3C(O)Me
25846-chloro-2,5-difluoropyridin-3-yl2.4,6-F3C(O)Me
25856-bromo-2,5-difluoropyridin-3-yl2.4,6-F3C(O)Me
25865-chloro-2,6-difluoropyridin-3-yl2.4,6-F3C(O)Me
25875-bromo-2,6-difluoropyridin-3-yl2.4,6-F3C(O)Me
25884,5,6-trifluoropyridin-3-yl2.4,6-F3C(O)Me
25894-chloro-5,6-difluoropyridin-3-yl2.4,6-F3C(O)Me
25904-bromo-5,6-difluoropyridin-3-yl2.4,6-F3C(O)Me
25915-chloro-4,6-difluoropyridin-3-yl2.4,6-F3C(O)Me
25925-bromo-4,6-difluoropyridin-3-yl2.4,6-F3C(O)Me
25936-chloro-4,5-difluoropyridin-3-yl2.4,6-F3C(O)Me
25946-bromo-4,5-difluoropyridin-3-yl2.4,6-F3C(O)Me
2595pyridin-3-yl2.4,6-F3C(O)Me
25966-fluoropyridin-3-yl2-FC(O)Me
25976-chloropyridin-3-yl2-FC(O)Me
25986-bromopyridin-3-yl2-FC(O)Me
25995-fluoropyridin-3-yl2-FC(O)Me
26005-chloropyridin-3-yl2-FC(O)Me
26015-bromopyridin-3-yl2-FC(O)Me
26024-fluoropyridin-3-yl2-FC(O)Me
26034-chloropyridin-3-yl2-FC(O)Me
26044-bromopyridin-3-yl2-FC(O)Me
26052-fluoropyridin-3-yl2-FC(O)Me
26062-chloropyridin-3-yl2-FC(O)Me
26072-bromopyridin-3-yl2-FC(O)Me
26082,6-difluoropyridin-3-yl2-FC(O)Me
26095-chloro-6-fluoropyridin-3-yl2-FC(O)Me
26105-bromo-6-fluoropyridin-3-yl2-FC(O)Me
26115,6-difluoropyridin-3-yl2-FC(O)Me
26126-chloro-5-fluoropyridin-3-yl2-FC(O)Me
26136-bromo-5-fluoropyridin-3-yl2-FC(O)Me
26144,5-difluoropyridin-3-yl2-FC(O)Me
26154-chloro-5-fluoropyridin-3-yl2-FC(O)Me
26164-bromo-5-fluoropyridin-3-yl2-FC(O)Me
26175-chloro-4-fluoropyridin-3-yl2-FC(O)Me
26184,5-dichloropyridin-3-yl2-FC(O)Me
26194-bromo-5-chloropyridin-3-yl2-FC(O)Me
26205-bromo-4-fluoropyridin-3-yl2-FC(O)Me
26215-bromo-4-chloropyridin-3-yl2-FC(O)Me
26224,5-dibromopyridin-3-yl2-FC(O)Me
26232,5,6-trifluoropyridin-3-yl2-FC(O)Me
26242-chloro-5,6-difluoropyridin-3-yl2-FC(O)Me
26252-bromo-5,6-difluoropyridin-3-yl2-FC(O)Me
26266-chloro-2,5-difluoropyridin-3-yl2-FC(O)Me
26276-bromo-2,5-difluoropyridin-3-yl2-FC(O)Me
26285-chloro-2,6-difluoropyridin-3-yl2-FC(O)Me
26295-bromo-2,6-difluoropyridin-3-yl2-FC(O)Me
26304,5,6-trifluoropyridin-3-yl2-FC(O)Me
26314-chloro-5,6-difluoropyridin-3-yl2-FC(O)Me
26324-bromo-5,6-difluoropyridin-3-yl2-FC(O)Me
26335-chloro-4,6-difluoropyridin-3-yl2-FC(O)Me
26345-bromo-4,6-difluoropyridin-3-yl2-FC(O)Me
26356-chloro-4,5-difluoropyridin-3-yl2-FC(O)Me
26366-bromo-4,5-difluoropyridin-3-yl2-FC(O)Me
2637pyridin-3-yl2-FC(O)Me
26386-fluoropyridin-3-yl2.3,6-F3C(O)Me
26396-chloropyridin-3-yl2.3,6-F3C(O)Me
26406-bromopyridin-3-yl2.3,6-F3C(O)Me
26415-fluoropyridin-3-yl2.3,6-F3C(O)Me
26425-chloropyridin-3-yl2.3,6-F3C(O)Me
26435-bromopyridin-3-yl2.3,6-F3C(O)Me
26444-fluoropyridin-3-yl2.3,6-F3C(O)Me
26454-chloropyridin-3-yl2.3,6-F3C(O)Me
26464-bromopyridin-3-yl2.3,6-F3C(O)Me
26472-fluoropyridin-3-yl2.3,6-F3C(O)Me
26482-chloropyridin-3-yl2.3,6-F3C(O)Me
26492-bromopyridin-3-yl2.3,6-F3C(O)Me
26502,6-difluoropyridin-3-yl2.3,6-F3C(O)Me
26515-chloro-6-fluoropyridin-3-yl2.3,6-F3C(O)Me
26525-bromo-6-fluoropyridin-3-yl2.3,6-F3C(O)Me
26535,6-difluoropyridin-3-yl2.3,6-F3C(O)Me
26546-chloro-5-fluoropyridin-3-yl2.3,6-F3C(O)Me
26556-bromo-5-fluoropyridin-3-yl2.3,6-F3C(O)Me
26564,5-difluoropyridin-3-yl2.3,6-F3C(O)Me
26574-chloro-5-fluoropyridin-3-yl2.3,6-F3C(O)Me
26584-bromo-5-fluoropyridin-3-yl2.3,6-F3C(O)Me
26595-chloro-4-fluoropyridin-3-yl2.3,6-F3C(O)Me
26604,5-dichloropyridin-3-yl2.3,6-F3C(O)Me
26614-bromo-5-chloropyridin-3-yl2.3,6-F3C(O)Me
26625-bromo-4-fluoropyridin-3-yl2.3,6-F3C(O)Me
26635-bromo-4-chloropyridin-3-yl2.3,6-F3C(O)Me
26644,5-dibromopyridin-3-yl2.3,6-F3C(O)Me
26652,5,6-trifluoropyridin-3-yl2.3,6-F3C(O)Me
26662-chloro-5,6-difluoropyridin-3-yl2.3,6-F3C(O)Me
26672-bromo-5,6-difluoropyridin-3-yl2.3,6-F3C(O)Me
26686-chloro-2,5-difluoropyridin-3-yl2.3,6-F3C(O)Me
26696-bromo-2,5-difluoropyridin-3-yl2.3,6-F3C(O)Me
26705-chloro-2,6-difluoropyridin-3-yl2.3,6-F3C(O)Me
26715-bromo-2,6-difluoropyridin-3-yl2.3,6-F3C(O)Me
26724,5,6-trifluoropyridin-3-yl2.3,6-F3C(O)Me
26734-chloro-5,6-difluoropyridin-3-yl2.3,6-F3C(O)Me
26744-bromo-5,6-difluoropyridin-3-yl2.3,6-F3C(O)Me
26755-chloro-4,6-difluoropyridin-3-yl2.3,6-F3C(O)Me
26765-bromo-4,6-difluoropyridin-3-yl2.3,6-F3C(O)Me
26776-chloro-4,5-difluoropyridin-3-yl2.3,6-F3C(O)Me
26786-bromo-4,5-difluoropyridin-3-yl2.3,6-F3C(O)Me
2679pyridin-3-yl2.3,6-F3C(O)Me
26806-fluoropyridin-3-yl3-NO2C(O)Me
26816-chloropyridin-3-yl3-NO2C(O)Me
26826-bromopyridin-3-yl3-NO2C(O)Me
26835-fluoropyridin-3-yl3-NO2C(O)Me
26845-chloropyridin-3-yl3-NO2C(O)Me
26855-bromopyridin-3-yl3-NO2C(O)Me
26864-fluoropyridin-3-yl3-NO2C(O)Me
26874-chloropyridin-3-yl3-NO2C(O)Me
26884-bromopyridin-3-yl3-NO2C(O)Me
26892-fluoropyridin-3-yl3-NO2C(O)Me
26902-chloropyridin-3-yl3-NO2C(O)Me
26912-bromopyridin-3-yl3-NO2C(O)Me
26922,6-difluoropyridin-3-yl3-NO2C(O)Me
26935-chloro-6-fluoropyridin-3-yl3-NO2C(O)Me
26945-bromo-6-fluoropyridin-3-yl3-NO2C(O)Me
26955,6-difluoropyridin-3-yl3-NO2C(O)Me
26966-chloro-5-fluoropyridin-3-yl3-NO2C(O)Me
26976-bromo-5-fluoropyridin-3-yl3-NO2C(O)Me
26984,5-difluoropyridin-3-yl3-NO2C(O)Me
26994-chloro-5-fluoropyridin-3-yl3-NO2C(O)Me
27004-bromo-5-fluoropyridin-3-yl3-NO2C(O)Me
27015-chloro-4-fluoropyridin-3-yl3-NO2C(O)Me
27024,5-dichloropyridin-3-yl3-NO2C(O)Me
27034-bromo-5-chloropyridin-3-yl3-NO2C(O)Me
27045-bromo-4-fluoropyridin-3-yl3-NO2C(O)Me
27055-bromo-4-chloropyridin-3-yl3-NO2C(O)Me
27064,5-dibromopyridin-3-yl3-NO2C(O)Me
27072,5,6-trifluoropyridin-3-yl3-NO2C(O)Me
27082-chloro-5,6-difluoropyridin-3-yl3-NO2C(O)Me
27092-bromo-5,6-difluoropyridin-3-yl3-NO2C(O)Me
27106-chloro-2,5-difluoropyridin-3-yl3-NO2C(O)Me
27116-bromo-2,5-difluoropyridin-3-yl3-NO2C(O)Me
27125-chloro-2,6-difluoropyridin-3-yl3-NO2C(O)Me
27135-bromo-2,6-difluoropyridin-3-yl3-NO2C(O)Me
27144,5,6-trifluoropyridin-3-yl3-NO2C(O)Me
27154-chloro-5,6-difluoropyridin-3-yl3-NO2C(O)Me
27164-bromo-5,6-difluoropyridin-3-yl3-NO2C(O)Me
27175-chloro-4,6-difluoropyridin-3-yl3-NO2C(O)Me
27185-bromo-4,6-difluoropyridin-3-yl3-NO2C(O)Me
27196-chloro-4,5-difluoropyridin-3-yl3-NO2C(O)Me
27206-bromo-4,5-difluoropyridin-3-yl3-NO2C(O)Me
2721pyridin-3-yl3-NO2C(O)Me
27226-fluoropyridin-3-yl4-NO2C(O)Me
27236-chloropyridin-3-yl4-NO2C(O)Me
27246-bromopyridin-3-yl4-NO2C(O)Me
27255-fluoropyridin-3-yl4-NO2C(O)Me
27265-chloropyridin-3-yl4-NO2C(O)Me
27275-bromopyridin-3-yl4-NO2C(O)Me
27284-fluoropyridin-3-yl4-NO2C(O)Me
27294-chloropyridin-3-yl4-NO2C(O)Me
27304-bromopyridin-3-yl4-NO2C(O)Me
27312-fluoropyridin-3-yl4-NO2C(O)Me
27322-chloropyridin-3-yl4-NO2C(O)Me
27332-bromopyridin-3-yl4-NO2C(O)Me
27342,6-difluoropyridin-3-yl4-NO2C(O)Me
27355-chloro-6-fluoropyridin-3-yl4-NO2C(O)Me
27365-bromo-6-fluoropyridin-3-yl4-NO2C(O)Me
27375,6-difluoropyridin-3-yl4-NO2C(O)Me
27386-chloro-5-fluoropyridin-3-yl4-NO2C(O)Me
27396-bromo-5-fluoropyridin-3-yl4-NO2C(O)Me
27404,5-difluoropyridin-3-yl4-NO2C(O)Me
27414-chloro-5-fluoropyridin-3-yl4-NO2C(O)Me
27424-bromo-5-fluoropyridin-3-yl4-NO2C(O)Me
27435-chloro-4-fluoropyridin-3-yl4-NO2C(O)Me
27444,5-dichloropyridin-3-yl4-NO2C(O)Me
27454-bromo-5-chloropyridin-3-yl4-NO2C(O)Me
27465-bromo-4-fluoropyridin-3-yl4-NO2C(O)Me
27475-bromo-4-chloropyridin-3-yl4-NO2C(O)Me
27484,5-dibromopyridin-3-yl4-NO2C(O)Me
27492,5,6-trifluoropyridin-3-yl4-NO2C(O)Me
27502-chloro-5,6-difluoropyridin-3-yl4-NO2C(O)Me
27512-bromo-5,6-difluoropyridin-3-yl4-NO2C(O)Me
27526-chloro-2,5-difluoropyridin-3-yl4-NO2C(O)Me
27536-bromo-2,5-difluoropyridin-3-yl4-NO2C(O)Me
27545-chloro-2,6-difluoropyridin-3-yl4-NO2C(O)Me
27555-bromo-2,6-difluoropyridin-3-yl4-NO2C(O)Me
27564,5,6-trifluoropyridin-3-yl4-NO2C(O)Me
27574-chloro-5,6-difluoropyridin-3-yl4-NO2C(O)Me
27584-bromo-5,6-difluoropyridin-3-yl4-NO2C(O)Me
27595-chloro-4,6-difluoropyridin-3-yl4-NO2C(O)Me
27605-bromo-4,6-difluoropyridin-3-yl4-NO2C(O)Me
27616-chloro-4,5-difluoropyridin-3-yl4-NO2C(O)Me
27626-bromo-4,5-difluoropyridin-3-yl4-NO2C(O)Me
2763pyridin-3-yl4-NO2C(O)Me
27646-fluoropyridin-3-yl4-OMeC(O)Me
27656-chloropyridin-3-yl4-OMeC(O)Me
27666-bromopyridin-3-yl4-OMeC(O)Me
27675-fluoropyridin-3-yl4-OMeC(O)Me
27685-chloropyridin-3-yl4-OMeC(O)Me
27695-bromopyridin-3-yl4-OMeC(O)Me
27704-fluoropyridin-3-yl4-OMeC(O)Me
27714-chloropyridin-3-yl4-OMeC(O)Me
27724-bromopyridin-3-yl4-OMeC(O)Me
27732-fluoropyridin-3-yl4-OMeC(O)Me
27742-chloropyridin-3-yl4-OMeC(O)Me
27752-bromopyridin-3-yl4-OMeC(O)Me
27762,6-difluoropyridin-3-yl4-OMeC(O)Me
27775-chloro-6-fluoropyridin-3-yl4-OMeC(O)Me
27785-bromo-6-fluoropyridin-3-yl4-OMeC(O)Me
27795,6-difluoropyridin-3-yl4-OMeC(O)Me
27806-chloro-5-fluoropyridin-3-yl4-OMeC(O)Me
27816-bromo-5-fluoropyridin-3-yl4-OMeC(O)Me
27824,5-difluoropyridin-3-yl4-OMeC(O)Me
27834-chloro-5-fluoropyridin-3-yl4-OMeC(O)Me
27844-bromo-5-fluoropyridin-3-yl4-OMeC(O)Me
27855-chloro-4-fluoropyridin-3-yl4-OMeC(O)Me
27864,5-dichloropyridin-3-yl4-OMeC(O)Me
27874-bromo-5-chloropyridin-3-yl4-OMeC(O)Me
27885-bromo-4-fluoropyridin-3-yl4-OMeC(O)Me
27895-bromo-4-chloropyridin-3-yl4-OMeC(O)Me
27904,5-dibromopyridin-3-yl4-OMeC(O)Me
27912,5,6-trifluoropyridin-3-yl4-OMeC(O)Me
27922-chloro-5,6-difluoropyridin-3-yl4-OMeC(O)Me
27932-bromo-5,6-difluoropyridin-3-yl4-OMeC(O)Me
27946-chloro-2,5-difluoropyridin-3-yl4-OMeC(O)Me
27956-bromo-2,5-difluoropyridin-3-yl4-OMeC(O)Me
27965-chloro-2,6-difluoropyridin-3-yl4-OMeC(O)Me
27975-bromo-2,6-difluoropyridin-3-yl4-OMeC(O)Me
27984,5,6-trifluoropyridin-3-yl4-OMeC(O)Me
27994-chloro-5,6-difluoropyridin-3-yl4-OMeC(O)Me
28004-bromo-5,6-difluoropyridin-3-yl4-OMeC(O)Me
28015-chloro-4,6-difluoropyridin-3-yl4-OMeC(O)Me
28025-bromo-4,6-difluoropyridin-3-yl4-OMeC(O)Me
28036-chloro-4,5-difluoropyridin-3-yl4-OMeC(O)Me
28046-bromo-4,5-difluoropyridin-3-yl4-OMeC(O)Me
2805pyridin-3-yl4-OMeC(O)Me
28066-fluoropyridin-3-yl4-CF3C(O)Me
28076-chloropyridin-3-yl4-CF3C(O)Me
28086-bromopyridin-3-yl4-CF3C(O)Me
28095-fluoropyridin-3-yl4-CF3C(O)Me
28105-chloropyridin-3-yl4-CF3C(O)Me
28115-bromopyridin-3-yl4-CF3C(O)Me
28124-fluoropyridin-3-yl4-CF3C(O)Me
28134-chloropyridin-3-yl4-CF3C(O)Me
28144-bromopyridin-3-yl4-CF3C(O)Me
28152-fluoropyridin-3-yl4-CF3C(O)Me
28162-chloropyridin-3-yl4-CF3C(O)Me
28172-bromopyridin-3-yl4-CF3C(O)Me
28182,6-difluoropyridin-3-yl4-CF3C(O)Me
28195-chloro-6-fluoropyridin-3-yl4-CF3C(O)Me
28205-bromo-6-fluoropyridin-3-yl4-CF3C(O)Me
28215,6-difluoropyridin-3-yl4-CF3C(O)Me
28226-chloro-5-fluoropyridin-3-yl4-CF3C(O)Me
28236-bromo-5-fluoropyridin-3-yl4-CF3C(O)Me
28244,5-difluoropyridin-3-yl4-CF3C(O)Me
28254-chloro-5-fluoropyridin-3-yl4-CF3C(O)Me
28264-bromo-5-fluoropyridin-3-yl4-CF3C(O)Me
28275-chloro-4-fluoropyridin-3-yl4-CF3C(O)Me
28284,5-dichloropyridin-3-yl4-CF3C(O)Me
28294-bromo-5-chloropyridin-3-yl4-CF3C(O)Me
28305-bromo-4-fluoropyridin-3-yl4-CF3C(O)Me
28315-bromo-4-chloropyridin-3-yl4-CF3C(O)Me
28324,5-dibromopyridin-3-yl4-CF3C(O)Me
28332,5,6-trifluoropyridin-3-yl4-CF3C(O)Me
28342-chloro-5,6-difluoropyridin-3-yl4-CF3C(O)Me
28352-bromo-5,6-difluoropyridin-3-yl4-CF3C(O)Me
28366-chloro-2,5-difluoropyridin-3-yl4-CF3C(O)Me
28376-bromo-2,5-difluoropyridin-3-yl4-CF3C(O)Me
28385-chloro-2,6-difluoropyridin-3-yl4-CF3C(O)Me
28395-bromo-2,6-difluoropyridin-3-yl4-CF3C(O)Me
28404,5,6-trifluoropyridin-3-yl4-CF3C(O)Me
28414-chloro-5,6-difluoropyridin-3-yl4-CF3C(O)Me
28424-bromo-5,6-difluoropyridin-3-yl4-CF3C(O)Me
28435-chloro-4,6-difluoropyridin-3-yl4-CF3C(O)Me
28445-bromo-4,6-difluoropyridin-3-yl4-CF3C(O)Me
28456-chloro-4,5-difluoropyridin-3-yl4-CF3C(O)Me
28466-bromo-4,5-difluoropyridin-3-yl4-CF3C(O)Me
2847pyridin-3-yl4-CF3C(O)Me
28486-fluoropyridin-3-yl4-ClC(O)Me
28496-chloropyridin-3-yl4-ClC(O)Me
28506-bromopyridin-3-yl4-ClC(O)Me
28515-fluoropyridin-3-yl4-ClC(O)Me
28525-chloropyridin-3-yl4-ClC(O)Me
28535-bromopyridin-3-yl4-ClC(O)Me
28544-fluoropyridin-3-yl4-ClC(O)Me
28554-chloropyridin-3-yl4-ClC(O)Me
28564-bromopyridin-3-yl4-ClC(O)Me
28572-fluoropyridin-3-yl4-ClC(O)Me
28582-chloropyridin-3-yl4-ClC(O)Me
28592-bromopyridin-3-yl4-ClC(O)Me
28602,6-difluoropyridin-3-yl4-ClC(O)Me
28615-chloro-6-fluoropyridin-3-yl4-ClC(O)Me
28625-bromo-6-fluoropyridin-3-yl4-ClC(O)Me
28635,6-difluoropyridin-3-yl4-ClC(O)Me
28646-chloro-5-fluoropyridin-3-yl4-ClC(O)Me
28656-bromo-5-fluoropyridin-3-yl4-ClC(O)Me
28664,5-difluoropyridin-3-yl4-ClC(O)Me
28674-chloro-5-fluoropyridin-3-yl4-ClC(O)Me
28684-bromo-5-fluoropyridin-3-yl4-ClC(O)Me
28695-chloro-4-fluoropyridin-3-yl4-ClC(O)Me
28704,5-dichloropyridin-3-yl4-ClC(O)Me
28714-bromo-5-chloropyridin-3-yl4-ClC(O)Me
28725-bromo-4-fluoropyridin-3-yl4-ClC(O)Me
28735-bromo-4-chloropyridin-3-yl4-ClC(O)Me
28744,5-dibromopyridin-3-yl4-ClC(O)Me
28752,5,6-trifluoropyridin-3-yl4-ClC(O)Me
28762-chloro-5,6-difluoropyridin-3-yl4-ClC(O)Me
28772-bromo-5,6-difluoropyridin-3-yl4-ClC(O)Me
28786-chloro-2,5-difluoropyridin-3-yl4-ClC(O)Me
28796-bromo-2,5-difluoropyridin-3-yl4-ClC(O)Me
28805-chloro-2,6-difluoropyridin-3-yl4-ClC(O)Me
28815-bromo-2,6-difluoropyridin-3-yl4-ClC(O)Me
28824,5,6-trifluoropyridin-3-yl4-ClC(O)Me
28834-chloro-5,6-difluoropyridin-3-yl4-ClC(O)Me
28844-bromo-5,6-difluoropyridin-3-yl4-ClC(O)Me
28855-chloro-4,6-difluoropyridin-3-yl4-ClC(O)Me
28865-bromo-4,6-difluoropyridin-3-yl4-ClC(O)Me
28876-chloro-4,5-difluoropyridin-3-yl4-ClC(O)Me
28886-bromo-4,5-difluoropyridin-3-yl4-ClC(O)Me
2889pyridin-3-yl4-ClC(O)Me
28906-fluoropyridin-3-yl4-FC(O)Me
28916-chloropyridin-3-yl4-FC(O)Me
28926-bromopyridin-3-yl4-FC(O)Me
28935-fluoropyridin-3-yl4-FC(O)Me
28945-chloropyridin-3-yl4-FC(O)Me
28955-bromopyridin-3-yl4-FC(O)Me
28964-fluoropyridin-3-yl4-FC(O)Me
28974-chloropyridin-3-yl4-FC(O)Me
28984-bromopyridin-3-yl4-FC(O)Me
28992-fluoropyridin-3-yl4-FC(O)Me
29002-chloropyridin-3-yl4-FC(O)Me
29012-bromopyridin-3-yl4-FC(O)Me
29022,6-difluoropyridin-3-yl4-FC(O)Me
29035-chloro-6-fluoropyridin-3-yl4-FC(O)Me
29045-bromo-6-fluoropyridin-3-yl4-FC(O)Me
29055,6-difluoropyridin-3-yl4-FC(O)Me
29066-chloro-5-fluoropyridin-3-yl4-FC(O)Me
29076-bromo-5-fluoropyridin-3-yl4-FC(O)Me
29084,5-difluoropyridin-3-yl4-FC(O)Me
29094-chloro-5-fluoropyridin-3-yl4-FC(O)Me
29104-bromo-5-fluoropyridin-3-yl4-FC(O)Me
29115-chloro-4-fluoropyridin-3-yl4-FC(O)Me
29124,5-dichloropyridin-3-yl4-FC(O)Me
29134-bromo-5-chloropyridin-3-yl4-FC(O)Me
29145-bromo-4-fluoropyridin-3-yl4-FC(O)Me
29155-bromo-4-chloropyridin-3-yl4-FC(O)Me
29164,5-dibromopyridin-3-yl4-FC(O)Me
29172,5,6-trifluoropyridin-3-yl4-FC(O)Me
29182-chloro-5,6-difluoropyridin-3-yl4-FC(O)Me
29192-bromo-5,6-difluoropyridin-3-yl4-FC(O)Me
29206-chloro-2,5-difluoropyridin-3-yl4-FC(O)Me
29216-bromo-2,5-difluoropyridin-3-yl4-FC(O)Me
29225-chloro-2,6-difluoropyridin-3-yl4-FC(O)Me
29235-bromo-2,6-difluoropyridin-3-yl4-FC(O)Me
29244,5,6-trifluoropyridin-3-yl4-FC(O)Me
29254-chloro-5,6-difluoropyridin-3-yl4-FC(O)Me
29264-bromo-5,6-difluoropyridin-3-yl4-FC(O)Me
29275-chloro-4,6-difluoropyridin-3-yl4-FC(O)Me
29285-bromo-4,6-difluoropyridin-3-yl4-FC(O)Me
29296-chloro-4,5-difluoropyridin-3-yl4-FC(O)Me
29306-bromo-4,5-difluoropyridin-3-yl4-FC(O)Me
2931pyridin-3-yl4-FC(O)Me
29326-fluoropyridin-3-yl3-OCF3C(O)Me
29336-chloropyridin-3-yl3-OCF3C(O)Me
29346-bromopyridin-3-yl3-OCF3C(O)Me
29355-fluoropyridin-3-yl3-OCF3C(O)Me
29365-chloropyridin-3-yl3-OCF3C(O)Me
29375-bromopyridin-3-yl3-OCF3C(O)Me
29384-fluoropyridin-3-yl3-OCF3C(O)Me
29394-chloropyridin-3-yl3-OCF3C(O)Me
29404-bromopyridin-3-yl3-OCF3C(O)Me
29412-fluoropyridin-3-yl3-OCF3C(O)Me
29422-chloropyridin-3-yl3-OCF3C(O)Me
29432-bromopyridin-3-yl3-OCF3C(O)Me
29442,6-difluoropyridin-3-yl3-OCF3C(O)Me
29455-chloro-6-fluoropyridin-3-yl3-OCF3C(O)Me
29465-bromo-6-fluoropyridin-3-yl3-OCF3C(O)Me
29475,6-difluoropyridin-3-yl3-OCF3C(O)Me
29486-chloro-5-fluoropyridin-3-yl3-OCF3C(O)Me
29496-bromo-5-fluoropyridin-3-yl3-OCF3C(O)Me
29504,5-difluoropyridin-3-yl3-OCF3C(O)Me
29514-chloro-5-fluoropyridin-3-yl3-OCF3C(O)Me
29524-bromo-5-fluoropyridin-3-yl3-OCF3C(O)Me
29535-chloro-4-fluoropyridin-3-yl3-OCF3C(O)Me
29544,5-dichloropyridin-3-yl3-OCF3C(O)Me
29554-bromo-5-chloropyridin-3-yl3-OCF3C(O)Me
29565-bromo-4-fluoropyridin-3-yl3-OCF3C(O)Me
29575-bromo-4-chloropyridin-3-yl3-OCF3C(O)Me
29584,5-dibromopyridin-3-yl3-OCF3C(O)Me
29592,5,6-trifluoropyridin-3-yl3-OCF3C(O)Me
29602-chloro-5,6-difluoropyridin-3-yl3-OCF3C(O)Me
29612-bromo-5,6-difluoropyridin-3-yl3-OCF3C(O)Me
29626-chloro-2,5-difluoropyridin-3-yl3-OCF3C(O)Me
29636-bromo-2,5-difluoropyridin-3-yl3-OCF3C(O)Me
29645-chloro-2,6-difluoropyridin-3-yl3-OCF3C(O)Me
29655-bromo-2,6-difluoropyridin-3-yl3-OCF3C(O)Me
29664,5,6-trifluoropyridin-3-yl3-OCF3C(O)Me
29674-chloro-5,6-difluoropyridin-3-yl3-OCF3C(O)Me
29684-bromo-5,6-difluoropyridin-3-yl3-OCF3C(O)Me
29695-chloro-4,6-difluoropyridin-3-yl3-OCF3C(O)Me
29705-bromo-4,6-difluoropyridin-3-yl3-OCF3C(O)Me
29716-chloro-4,5-difluoropyridin-3-yl3-OCF3C(O)Me
29726-bromo-4,5-difluoropyridin-3-yl3-OCF3C(O)Me
2973pyridin-3-yl3-OCF3C(O)Me
29746-fluoropyridin-3-yl4-OCF3C(O)Me
29756-chloropyridin-3-yl4-OCF3C(O)Me
29766-bromopyridin-3-yl4-OCF3C(O)Me
29775-fluoropyridin-3-yl4-OCF3C(O)Me
29785-chloropyridin-3-yl4-OCF3C(O)Me
29795-bromopyridin-3-yl4-OCF3C(O)Me
29804-fluoropyridin-3-yl4-OCF3C(O)Me
29814-chloropyridin-3-yl4-OCF3C(O)Me
29824-bromopyridin-3-yl4-OCF3C(O)Me
29832-fluoropyridin-3-yl4-OCF3C(O)Me
29842-chloropyridin-3-yl4-OCF3C(O)Me
29852-bromopyridin-3-yl4-OCF3C(O)Me
29862,6-difluoropyridin-3-yl4-OCF3C(O)Me
29875-chloro-6-fluoropyridin-3-yl4-OCF3C(O)Me
29885-bromo-6-fluoropyridin-3-yl4-OCF3C(O)Me
29895,6-difluoropyridin-3-yl4-OCF3C(O)Me
29906-chloro-5-fluoropyridin-3-yl4-OCF3C(O)Me
29916-bromo-5-fluoropyridin-3-yl4-OCF3C(O)Me
29924,5-difluoropyridin-3-yl4-OCF3C(O)Me
29934-chloro-5-fluoropyridin-3-yl4-OCF3C(O)Me
29944-bromo-5-fluoropyridin-3-yl4-OCF3C(O)Me
29955-chloro-4-fluoropyridin-3-yl4-OCF3C(O)Me
29964,5-dichloropyridin-3-yl4-OCF3C(O)Me
29974-bromo-5-chloropyridin-3-yl4-OCF3C(O)Me
29985-bromo-4-fluoropyridin-3-yl4-OCF3C(O)Me
29995-bromo-4-chloropyridin-3-yl4-OCF3C(O)Me
30004,5-dibromopyridin-3-yl4-OCF3C(O)Me
30012,5,6-trifluoropyridin-3-yl4-OCF3C(O)Me
30022-chloro-5,6-difluoropyridin-3-yl4-OCF3C(O)Me
30032-bromo-5,6-difluoropyridin-3-yl4-OCF3C(O)Me
30046-chloro-2,5-difluoropyridin-3-yl4-OCF3C(O)Me
30056-bromo-2,5-difluoropyridin-3-yl4-OCF3C(O)Me
30065-chloro-2,6-difluoropyridin-3-yl4-OCF3C(O)Me
30075-bromo-2,6-difluoropyridin-3-yl4-OCF3C(O)Me
30084,5,6-trifluoropyridin-3-yl4-OCF3C(O)Me
30094-chloro-5,6-difluoropyridin-3-yl4-OCF3C(O)Me
30104-bromo-5,6-difluoropyridin-3-yl4-OCF3C(O)Me
30115-chloro-4,6-difluoropyridin-3-yl4-OCF3C(O)Me
30125-bromo-4,6-difluoropyridin-3-yl4-OCF3C(O)Me
30136-chloro-4,5-difluoropyridin-3-yl4-OCF3C(O)Me
30146-bromo-4,5-difluoropyridin-3-yl4-OCF3C(O)Me
3015pyridin-3-yl4-OCF3C(O)Me
30166-fluoropyridin-3-yl3-CNC(O)Me
30176-chloropyridin-3-yl3-CNC(O)Me
30186-bromopyridin-3-yl3-CNC(O)Me
30195-fluoropyridin-3-yl3-CNC(O)Me
30205-chloropyridin-3-yl3-CNC(O)Me
30215-bromopyridin-3-yl3-CNC(O)Me
30224-fluoropyridin-3-yl3-CNC(O)Me
30234-chloropyridin-3-yl3-CNC(O)Me
30244-bromopyridin-3-yl3-CNC(O)Me
30252-fluoropyridin-3-yl3-CNC(O)Me
30262-chloropyridin-3-yl3-CNC(O)Me
30272-bromopyridin-3-yl3-CNC(O)Me
30282,6-difluoropyridin-3-yl3-CNC(O)Me
30295-chloro-6-fluoropyridin-3-yl3-CNC(O)Me
30305-bromo-6-fluoropyridin-3-yl3-CNC(O)Me
30315,6-difluoropyridin-3-yl3-CNC(O)Me
30326-chloro-5-fluoropyridin-3-yl3-CNC(O)Me
30336-bromo-5-fluoropyridin-3-yl3-CNC(O)Me
30344,5-difluoropyridin-3-yl3-CNC(O)Me
30354-chloro-5-fluoropyridin-3-yl3-CNC(O)Me
30364-bromo-5-fluoropyridin-3-yl3-CNC(O)Me
30375-chloro-4-fluoropyridin-3-yl3-CNC(O)Me
30384,5-dichloropyridin-3-yl3-CNC(O)Me
30394-bromo-5-chloropyridin-3-yl3-CNC(O)Me
30405-bromo-4-fluoropyridin-3-yl3-CNC(O)Me
30415-bromo-4-chloropyridin-3-yl3-CNC(O)Me
30424,5-dibromopyridin-3-yl3-CNC(O)Me
30432,5,6-trifluoropyridin-3-yl3-CNC(O)Me
30442-chloro-5,6-difluoropyridin-3-yl3-CNC(O)Me
30452-bromo-5,6-difluoropyridin-3-yl3-CNC(O)Me
30466-chloro-2,5-difluoropyridin-3-yl3-CNC(O)Me
30476-bromo-2,5-difluoropyridin-3-yl3-CNC(O)Me
30485-chloro-2,6-difluoropyridin-3-yl3-CNC(O)Me
30495-bromo-2,6-difluoropyridin-3-yl3-CNC(O)Me
30504,5,6-trifluoropyridin-3-yl3-CNC(O)Me
30514-chloro-5,6-difluoropyridin-3-yl3-CNC(O)Me
30524-bromo-5,6-difluoropyridin-3-yl3-CNC(O)Me
30535-chloro-4,6-difluoropyridin-3-yl3-CNC(O)Me
30545-bromo-4,6-difluoropyridin-3-yl3-CNC(O)Me
30556-chloro-4,5-difluoropyridin-3-yl3-CNC(O)Me
30566-bromo-4,5-difluoropyridin-3-yl3-CNC(O)Me
3057pyridin-3-yl3-CNC(O)Me
30586-fluoropyridin-3-yl4-CNC(O)Me
30596-chloropyridin-3-yl4-CNC(O)Me
30606-bromopyridin-3-yl4-CNC(O)Me
30615-fluoropyridin-3-yl4-CNC(O)Me
30625-chloropyridin-3-yl4-CNC(O)Me
30635-bromopyridin-3-yl4-CNC(O)Me
30644-fluoropyridin-3-yl4-CNC(O)Me
30654-chloropyridin-3-yl4-CNC(O)Me
30664-bromopyridin-3-yl4-CNC(O)Me
30672-fluoropyridin-3-yl4-CNC(O)Me
30682-chloropyridin-3-yl4-CNC(O)Me
30692-bromopyridin-3-yl4-CNC(O)Me
30702,6-difluoropyridin-3-yl4-CNC(O)Me
30715-chloro-6-fluoropyridin-3-yl4-CNC(O)Me
30725-bromo-6-fluoropyridin-3-yl4-CNC(O)Me
30735,6-difluoropyridin-3-yl4-CNC(O)Me
30746-chloro-5-fluoropyridin-3-yl4-CNC(O)Me
30756-bromo-5-fluoropyridin-3-yl4-CNC(O)Me
30764,5-difluoropyridin-3-yl4-CNC(O)Me
30774-chloro-5-fluoropyridin-3-yl4-CNC(O)Me
30784-bromo-5-fluoropyridin-3-yl4-CNC(O)Me
30795-chloro-4-fluoropyridin-3-yl4-CNC(O)Me
30804,5-dichloropyridin-3-yl4-CNC(O)Me
30814-bromo-5-chloropyridin-3-yl4-CNC(O)Me
30825-bromo-4-fluoropyridin-3-yl4-CNC(O)Me
30835-bromo-4-chloropyridin-3-yl4-CNC(O)Me
30844,5-dibromopyridin-3-yl4-CNC(O)Me
30852,5,6-trifluoropyridin-3-yl4-CNC(O)Me
30862-chloro-5,6-difluoropyridin-3-yl4-CNC(O)Me
30872-bromo-5,6-difluoropyridin-3-yl4-CNC(O)Me
30886-chloro-2,5-difluoropyridin-3-yl4-CNC(O)Me
30896-bromo-2,5-difluoropyridin-3-yl4-CNC(O)Me
30905-chloro-2,6-difluoropyridin-3-yl4-CNC(O)Me
30915-bromo-2,6-difluoropyridin-3-yl4-CNC(O)Me
30924,5,6-trifluoropyridin-3-yl4-CNC(O)Me
30934-chloro-5,6-difluoropyridin-3-yl4-CNC(O)Me
30944-bromo-5,6-difluoropyridin-3-yl4-CNC(O)Me
30955-chloro-4,6-difluoropyridin-3-yl4-CNC(O)Me
30965-bromo-4,6-difluoropyridin-3-yl4-CNC(O)Me
30976-chloro-4,5-difluoropyridin-3-yl4-CNC(O)Me
30986-bromo-4,5-difluoropyridin-3-yl4-CNC(O)Me
3099pyridin-3-yl4-CNC(O)Me

[0000]

Preferred meanings of Q(R2)n, (R3)mand R1in compounds of the formula (I) according to the invention
No.Q(R2)n(R3)mR1
31006-fluoropyridin-3-yl2.3-F2C(O)CF3
31016-chloropyridin-3-yl2.3-F2C(O)CF3
31026-bromopyridin-3-yl2.3-F2C(O)CF3
31035-fluoropyridin-3-yl2.3-F2C(O)CF3
31045-chloropyridin-3-yl2.3-F2C(O)CF3
31055-bromopyridin-3-yl2.3-F2C(O)CF3
31064-fluoropyridin-3-yl2.3-F2C(O)CF3
31074-chloropyridin-3-yl2.3-F2C(O)CF3
31084-bromopyridin-3-yl2.3-F2C(O)CF3
31092-fluoropyridin-3-yl2.3-F2C(O)CF3
31102-chloropyridin-3-yl2.3-F2C(O)CF3
31112-bromopyridin-3-yl2.3-F2C(O)CF3
31122,6-difluoropyridin-3-yl2.3-F2C(O)CF3
31135-chloro-6-fluoropyridin-3-yl2.3-F2C(O)CF3
31145-bromo-6-fluoropyridin-3-yl2.3-F2C(O)CF3
31155,6-difluoropyridin-3-yl2.3-F2C(O)CF3
31166-chloro-5-fluoropyridin-3-yl2.3-F2C(O)CF3
31176-bromo-5-fluoropyridin-3-yl2.3-F2C(O)CF3
31184,5-difluoropyridin-3-yl2.3-F2C(O)CF3
31194-chloro-5-fluoropyridin-3-yl2.3-F2C(O)CF3
31204-bromo-5-fluoropyridin-3-yl2.3-F2C(O)CF3
31215-chloro-4-fluoropyridin-3-yl2.3-F2C(O)CF3
31224,5-dichloropyridin-3-yl2.3-F2C(O)CF3
31234-bromo-5-chloropyridin-3-yl2.3-F2C(O)CF3
31245-bromo-4-fluoropyridin-3-yl2.3-F2C(O)CF3
31255-bromo-4-chloropyridin-3-yl2.3-F2C(O)CF3
31264,5-dibromopyridin-3-yl2.3-F2C(O)CF3
31272,5,6-trifluoropyridin-3-yl2.3-F2C(O)CF3
31282-chloro-5,6-difluoropyridin-3-yl2.3-F2C(O)CF3
31292-bromo-5,6-difluoropyridin-3-yl2.3-F2C(O)CF3
31306-chloro-2,5-difluoropyridin-3-yl2.3-F2C(O)CF3
31316-bromo-2,5-difluoropyridin-3-yl2.3-F2C(O)CF3
31325-chloro-2,6-difluoropyridin-3-yl2.3-F2C(O)CF3
31335-bromo-2,6-difluoropyridin-3-yl2.3-F2C(O)CF3
31344,5,6-trifluoropyridin-3-yl2.3-F2C(O)CF3
31354-chloro-5,6-difluoropyridin-3-yl2.3-F2C(O)CF3
31364-bromo-5,6-difluoropyridin-3-yl2.3-F2C(O)CF3
31375-chloro-4,6-difluoropyridin-3-yl2.3-F2C(O)CF3
31385-bromo-4,6-difluoropyridin-3-yl2.3-F2C(O)CF3
31396-chloro-4,5-difluoropyridin-3-yl2.3-F2C(O)CF3
31406-bromo-4,5-difluoropyridin-3-yl2.3-F2C(O)CF3
3141pyridin-3-yl2.3-F2C(O)CF3
31426-fluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31436-chloropyridin-3-yl2.6-F2.4—ClC(O)CF3
31446-bromopyridin-3-yl2.6-F2.4—ClC(O)CF3
31455-fluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31465-chloropyridin-3-yl2.6-F2.4—ClC(O)CF3
31475-bromopyridin-3-yl2.6-F2.4—ClC(O)CF3
31484-fluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31494-chloropyridin-3-yl2.6-F2.4—ClC(O)CF3
31504-bromopyridin-3-yl2.6-F2.4—ClC(O)CF3
31512-fluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31522-chloropyridin-3-yl2.6-F2.4—ClC(O)CF3
31532-bromopyridin-3-yl2.6-F2.4—ClC(O)CF3
31542,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31555-chloro-6-fluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31565-bromo-6-fluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31575,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31586-chloro-5-fluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31596-bromo-5-fluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31604,5-difluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31614-chloro-5-fluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31624-bromo-5-fluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31635-chloro-4-fluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31644,5-dichloropyridin-3-yl2.6-F2.4—ClC(O)CF3
31654-bromo-5-chloropyridin-3-yl2.6-F2.4—ClC(O)CF3
31665-bromo-4-fluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31675-bromo-4-chloropyridin-3-yl2.6-F2.4—ClC(O)CF3
31684,5-dibromopyridin-3-yl2.6-F2.4—ClC(O)CF3
31692,5,6-trifluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31702-chloro-5,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31712-bromo-5,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31726-chloro-2,5-difluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31736-bromo-2,5-difluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31745-chloro-2,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31755-bromo-2,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31764,5,6-trifluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31774-chloro-5,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31784-bromo-5,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31795-chloro-4,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31805-bromo-4,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31816-chloro-4,5-difluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31826-bromo-4,5-difluoropyridin-3-yl2.6-F2.4—ClC(O)CF3
31836-fluoropyridin-3-yl2.3,6-F3C(O)CF3
31846-chloropyridin-3-yl2.3,6-F3C(O)CF3
31856-bromopyridin-3-yl2.3,6-F3C(O)CF3
31865-fluoropyridin-3-yl2.3,6-F3C(O)CF3
31875-chloropyridin-3-yl2.3,6-F3C(O)CF3
31885-bromopyridin-3-yl2.3,6-F3C(O)CF3
31894-fluoropyridin-3-yl2.3,6-F3C(O)CF3
31904-chloropyridin-3-yl2.3,6-F3C(O)CF3
31914-bromopyridin-3-yl2.3,6-F3C(O)CF3
31922-fluoropyridin-3-yl2.3,6-F3C(O)CF3
31932-chloropyridin-3-yl2.3,6-F3C(O)CF3
31942-bromopyridin-3-yl2.3,6-F3C(O)CF3
31952,6-difluoropyridin-3-yl2.3,6-F3C(O)CF3
31965-chloro-6-fluoropyridin-3-yl2.3,6-F3C(O)CF3
31975-bromo-6-fluoropyridin-3-yl2.3,6-F3C(O)CF3
31985,6-difluoropyridin-3-yl2.3,6-F3C(O)CF3
31996-chloro-5-fluoropyridin-3-yl2.3,6-F3C(O)CF3
32006-bromo-5-fluoropyridin-3-yl2.3,6-F3C(O)CF3
32014,5-difluoropyridin-3-yl2.3,6-F3C(O)CF3
32024-chloro-5-fluoropyridin-3-yl2.3,6-F3C(O)CF3
32034-bromo-5-fluoropyridin-3-yl2.3,6-F3C(O)CF3
32045-chloro-4-fluoropyridin-3-yl2.3,6-F3C(O)CF3
32054,5-dichloropyridin-3-yl2.3,6-F3C(O)CF3
32064-bromo-5-chloropyridin-3-yl2.3,6-F3C(O)CF3
32075-bromo-4-fluoropyridin-3-yl2.3,6-F3C(O)CF3
32085-bromo-4-chloropyridin-3-yl2.3,6-F3C(O)CF3
32094,5-dibromopyridin-3-yl2.3,6-F3C(O)CF3
32102,5,6-trifluoropyridin-3-yl2.3,6-F3C(O)CF3
32112-chloro-5,6-difluoropyridin-3-yl2.3,6-F3C(O)CF3
32122-bromo-5,6-difluoropyridin-3-yl2.3,6-F3C(O)CF3
32136-chloro-2,5-difluoropyridin-3-yl2.3,6-F3C(O)CF3
32146-bromo-2,5-difluoropyridin-3-yl2.3,6-F3C(O)CF3
32155-chloro-2,6-difluoropyridin-3-yl2.3,6-F3C(O)CF3
32165-bromo-2,6-difluoropyridin-3-yl2.3,6-F3C(O)CF3
32174,5,6-trifluoropyridin-3-yl2.3,6-F3C(O)CF3
32184-chloro-5,6-difluoropyridin-3-yl2.3,6-F3C(O)CF3
32194-bromo-5,6-difluoropyridin-3-yl2.3,6-F3C(O)CF3
32205-chloro-4,6-difluoropyridin-3-yl2.3,6-F3C(O)CF3
32215-bromo-4,6-difluoropyridin-3-yl2.3,6-F3C(O)CF3
32226-chloro-4,5-difluoropyridin-3-yl2.3,6-F3C(O)CF3
32236-bromo-4,5-difluoropyridin-3-yl2.3,6-F3C(O)CF3
3224pyridin-3-yl2.3,6-F3C(O)CF3
32256-fluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32266-chloropyridin-3-yl2.3-F2C(O)C(O)OMe
32276-bromopyridin-3-yl2.3-F2C(O)C(O)OMe
32285-fluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32295-chloropyridin-3-yl2.3-F2C(O)C(O)OMe
32305-bromopyridin-3-yl2.3-F2C(O)C(O)OMe
32314-fluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32324-chloropyridin-3-yl2.3-F2C(O)C(O)OMe
32334-bromopyridin-3-yl2.3-F2C(O)C(O)OMe
32342-fluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32352-chloropyridin-3-yl2.3-F2C(O)C(O)OMe
32362-bromopyridin-3-yl2.3-F2C(O)C(O)OMe
32372,6-difluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32385-chloro-6-fluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32395-bromo-6-fluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32405,6-difluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32416-chloro-5-fluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32426-bromo-5-fluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32434,5-difluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32444-chloro-5-fluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32454-bromo-5-fluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32465-chloro-4-fluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32474,5-dichloropyridin-3-yl2.3-F2C(O)C(O)OMe
32484-bromo-5-chloropyridin-3-yl2.3-F2C(O)C(O)OMe
32495-bromo-4-fluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32505-bromo-4-chloropyridin-3-yl2.3-F2C(O)C(O)OMe
32514,5-dibromopyridin-3-yl2.3-F2C(O)C(O)OMe
32522,5,6-trifluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32532-chloro-5,6-difluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32542-bromo-5,6-difluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32556-chloro-2,5-difluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32566-bromo-2,5-difluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32575-chloro-2,6-difluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32585-bromo-2,6-difluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32594,5,6-trifluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32604-chloro-5,6-difluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32614-bromo-5,6-difluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32625-chloro-4,6-difluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32635-bromo-4,6-difluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32646-chloro-4,5-difluoropyridin-3-yl2.3-F2C(O)C(O)OMe
32656-bromo-4,5-difluoropyridin-3-yl2.3-F2C(O)C(O)OMe
3266pyridin-3-yl2.3-F2C(O)C(O)OMe
32676-fluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32686-chloropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32696-bromopyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32705-fluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32715-chloropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32725-bromopyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32734-fluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32744-chloropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32754-bromopyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32762-fluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32772-chloropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32782-bromopyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32792,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32805-chloro-6-fluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32815-bromo-6-fluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32825,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32836-chloro-5-fluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32846-bromo-5-fluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32854,5-difluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32864-chloro-5-fluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32874-bromo-5-fluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32885-chloro-4-fluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32894,5-dichloropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32904-bromo-5-chloropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32915-bromo-4-fluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32925-bromo-4-chloropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32934,5-dibromopyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32942,5,6-trifluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32952-chloro-5,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32962-bromo-5,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32976-chloro-2,5-difluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32986-bromo-2,5-difluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
32995-chloro-2,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
33005-bromo-2,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
33014,5,6-trifluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
33024-chloro-5,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
33034-bromo-5,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
33045-chloro-4,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
33055-bromo-4,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
33066-chloro-4,5-difluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
33076-bromo-4,5-difluoropyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
3308pyridin-3-yl2.6-F2.4—ClC(O)C(O)OMe
33096-fluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33106-chloropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33116-bromopyridin-3-yl2.3,6-F3C(O)C(O)OMe
33125-fluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33135-chloropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33145-bromopyridin-3-yl2.3,6-F3C(O)C(O)OMe
33154-fluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33164-chloropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33174-bromopyridin-3-yl2.3,6-F3C(O)C(O)OMe
33182-fluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33192-chloropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33202-bromopyridin-3-yl2.3,6-F3C(O)C(O)OMe
33212,6-difluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33225-chloro-6-fluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33235-bromo-6-fluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33245,6-difluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33256-chloro-5-fluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33266-bromo-5-fluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33274,5-difluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33284-chloro-5-fluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33294-bromo-5-fluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33305-chloro-4-fluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33314,5-dichloropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33324-bromo-5-chloropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33335-bromo-4-fluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33345-bromo-4-chloropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33354,5-dibromopyridin-3-yl2.3,6-F3C(O)C(O)OMe
33362,5,6-trifluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33372-chloro-5,6-difluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33382-bromo-5,6-difluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33396-chloro-2,5-difluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33406-bromo-2,5-difluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33415-chloro-2,6-difluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33425-bromo-2,6-difluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33434,5,6-trifluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33444-chloro-5,6-difluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33454-bromo-5,6-difluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33465-chloro-4,6-difluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33475-bromo-4,6-difluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33486-chloro-4,5-difluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
33496-bromo-4,5-difluoropyridin-3-yl2.3,6-F3C(O)C(O)OMe
3350pyridin-3-yl2.3,6-F3C(O)C(O)OMe
33516-fluoropyridin-3-yl2.3-F2C(O)Ph
33526-chloropyridin-3-yl2.3-F2C(O)Ph
33536-bromopyridin-3-yl2.3-F2C(O)Ph
33545-fluoropyridin-3-yl2.3-F2C(O)Ph
33555-chloropyridin-3-yl2.3-F2C(O)Ph
33565-bromopyridin-3-yl2.3-F2C(O)Ph
33574-fluoropyridin-3-yl2.3-F2C(O)Ph
33584-chloropyridin-3-yl2.3-F2C(O)Ph
33594-bromopyridin-3-yl2.3-F2C(O)Ph
33602-fluoropyridin-3-yl2.3-F2C(O)Ph
33612-chloropyridin-3-yl2.3-F2C(O)Ph
33622-bromopyridin-3-yl2.3-F2C(O)Ph
33632,6-difluoropyridin-3-yl2.3-F2C(O)Ph
33645-chloro-6-fluoropyridin-3-yl2.3-F2C(O)Ph
33655-bromo-6-fluoropyridin-3-yl2.3-F2C(O)Ph
33665,6-difluoropyridin-3-yl2.3-F2C(O)Ph
33676-chloro-5-fluoropyridin-3-yl2.3-F2C(O)Ph
33686-bromo-5-fluoropyridin-3-yl2.3-F2C(O)Ph
33694,5-difluoropyridin-3-yl2.3-F2C(O)Ph
33704-chloro-5-fluoropyridin-3-yl2.3-F2C(O)Ph
33714-bromo-5-fluoropyridin-3-yl2.3-F2C(O)Ph
33725-chloro-4-fluoropyridin-3-yl2.3-F2C(O)Ph
33734,5-dichloropyridin-3-yl2.3-F2C(O)Ph
33744-bromo-5-chloropyridin-3-yl2.3-F2C(O)Ph
33755-bromo-4-fluoropyridin-3-yl2.3-F2C(O)Ph
33765-bromo-4-chloropyridin-3-yl2.3-F2C(O)Ph
33774,5-dibromopyridin-3-yl2.3-F2C(O)Ph
33782,5,6-trifluoropyridin-3-yl2.3-F2C(O)Ph
33792-chloro-5,6-difluoropyridin-3-yl2.3-F2C(O)Ph
33802-bromo-5,6-difluoropyridin-3-yl2.3-F2C(O)Ph
33816-chloro-2,5-difluoropyridin-3-yl2.3-F2C(O)Ph
33826-bromo-2,5-difluoropyridin-3-yl2.3-F2C(O)Ph
33835-chloro-2,6-difluoropyridin-3-yl2.3-F2C(O)Ph
33845-bromo-2,6-difluoropyridin-3-yl2.3-F2C(O)Ph
33854,5,6-trifluoropyridin-3-yl2.3-F2C(O)Ph
33864-chloro-5,6-difluoropyridin-3-yl2.3-F2C(O)Ph
33874-bromo-5,6-difluoropyridin-3-yl2.3-F2C(O)Ph
33885-chloro-4,6-difluoropyridin-3-yl2.3-F2C(O)Ph
33895-bromo-4,6-difluoropyridin-3-yl2.3-F2C(O)Ph
33906-chloro-4,5-difluoropyridin-3-yl2.3-F2C(O)Ph
33916-bromo-4,5-difluoropyridin-3-yl2.3-F2C(O)Ph
3392pyridin-3-yl2.3-F2C(O)Ph
33936-fluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
33946-chloropyridin-3-yl2.6-F2.4—ClC(O)Ph
33956-bromopyridin-3-yl2.6-F2.4—ClC(O)Ph
33965-fluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
33975-chloropyridin-3-yl2.6-F2.4—ClC(O)Ph
33985-bromopyridin-3-yl2.6-F2.4—ClC(O)Ph
33994-fluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34004-chloropyridin-3-yl2.6-F2.4—ClC(O)Ph
34014-bromopyridin-3-yl2.6-F2.4—ClC(O)Ph
34022-fluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34032-chloropyridin-3-yl2.6-F2.4—ClC(O)Ph
34042-bromopyridin-3-yl2.6-F2.4—ClC(O)Ph
34052,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34065-chloro-6-fluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34075-bromo-6-fluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34085,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34096-chloro-5-fluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34106-bromo-5-fluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34114,5-difluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34124-chloro-5-fluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34134-bromo-5-fluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34145-chloro-4-fluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34154,5-dichloropyridin-3-yl2.6-F2.4—ClC(O)Ph
34164-bromo-5-chloropyridin-3-yl2.6-F2.4—ClC(O)Ph
34175-bromo-4-fluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34185-bromo-4-chloropyridin-3-yl2.6-F2.4—ClC(O)Ph
34194,5-dibromopyridin-3-yl2.6-F2.4—ClC(O)Ph
34202,5,6-trifluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34212-chloro-5,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34222-bromo-5,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34236-chloro-2,5-difluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34246-bromo-2,5-difluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34255-chloro-2,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34265-bromo-2,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34274,5,6-trifluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34284-chloro-5,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34294-bromo-5,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34305-chloro-4,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34315-bromo-4,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34326-chloro-4,5-difluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
34336-bromo-4,5-difluoropyridin-3-yl2.6-F2.4—ClC(O)Ph
3434pyridin-3-yl2.6-F2.4—ClC(O)Ph
3435pyridin-2-yl2.6-F2.4—ClC(O)Ph
3436pyridin-4-yl2.6-F2.4—ClC(O)Ph
34376-chloropyridin-3-yl2.3,6-F3C(O)Ph
34386-bromopyridin-3-yl2.3,6-F3C(O)Ph
34395-fluoropyridin-3-yl2.3,6-F3C(O)Ph
34405-chloropyridin-3-yl2.3,6-F3C(O)Ph
34415-bromopyridin-3-yl2.3,6-F3C(O)Ph
34424-fluoropyridin-3-yl2.3,6-F3C(O)Ph
34434-chloropyridin-3-yl2.3,6-F3C(O)Ph
34444-bromopyridin-3-yl2.3,6-F3C(O)Ph
34452-fluoropyridin-3-yl2.3,6-F3C(O)Ph
34462-chloropyridin-3-yl2.3,6-F3C(O)Ph
34472-bromopyridin-3-yl2.3,6-F3C(O)Ph
34482,6-difluoropyridin-3-yl2.3,6-F3C(O)Ph
34495-chloro-6-fluoropyridin-3-yl2.3,6-F3C(O)Ph
34505-bromo-6-fluoropyridin-3-yl2.3,6-F3C(O)Ph
34515,6-difluoropyridin-3-yl2.3,6-F3C(O)Ph
34526-chloro-5-fluoropyridin-3-yl2.3,6-F3C(O)Ph
34536-bromo-5-fluoropyridin-3-yl2.3,6-F3C(O)Ph
34544,5-difluoropyridin-3-yl2.3,6-F3C(O)Ph
34554-chloro-5-fluoropyridin-3-yl2.3,6-F3C(O)Ph
34564-bromo-5-fluoropyridin-3-yl2.3,6-F3C(O)Ph
34575-chloro-4-fluoropyridin-3-yl2.3,6-F3C(O)Ph
34584,5-dichloropyridin-3-yl2.3,6-F3C(O)Ph
34594-bromo-5-chloropyridin-3-yl2.3,6-F3C(O)Ph
34605-bromo-4-fluoropyridin-3-yl2.3,6-F3C(O)Ph
34615-bromo-4-chloropyridin-3-yl2.3,6-F3C(O)Ph
34624,5-dibromopyridin-3-yl2.3,6-F3C(O)Ph
34632,5,6-trifluoropyridin-3-yl2.3,6-F3C(O)Ph
34642-chloro-5,6-difluoropyridin-3-yl2.3,6-F3C(O)Ph
34652-bromo-5,6-difluoropyridin-3-yl2.3,6-F3C(O)Ph
34666-chloro-2,5-difluoropyridin-3-yl2.3,6-F3C(O)Ph
34676-bromo-2,5-difluoropyridin-3-yl2.3,6-F3C(O)Ph
34685-chloro-2,6-difluoropyridin-3-yl2.3,6-F3C(O)Ph
34695-bromo-2,6-difluoropyridin-3-yl2.3,6-F3C(O)Ph
34704,5,6-trifluoropyridin-3-yl2.3,6-F3C(O)Ph
34714-chloro-5,6-difluoropyridin-3-yl2.3,6-F3C(O)Ph
34724-bromo-5,6-difluoropyridin-3-yl2.3,6-F3C(O)Ph
34735-chloro-4,6-difluoropyridin-3-yl2.3,6-F3C(O)Ph
34745-bromo-4,6-difluoropyridin-3-yl2.3,6-F3C(O)Ph
34756-chloro-4,5-difluoropyridin-3-yl2.3,6-F3C(O)Ph
34766-bromo-4,5-difluoropyridin-3-yl2.3,6-F3C(O)Ph
3477pyridin-3-yl2.3,6-F3C(O)Ph
34786-fluoropyridin-3-yl2.3-F22-Bromacetyl
34796-chloropyridin-3-yl2.3-F22-Bromacetyl
34806-bromopyridin-3-yl2.3-F22-Bromacetyl
34815-fluoropyridin-3-yl2.3-F22-Bromacetyl
34825-chloropyridin-3-yl2.3-F22-Bromacetyl
34835-bromopyridin-3-yl2.3-F22-Bromacetyl
34844-fluoropyridin-3-yl2.3-F22-Bromacetyl
34854-chloropyridin-3-yl2.3-F22-Bromacetyl
34864-bromopyridin-3-yl2.3-F22-Bromacetyl
34872-fluoropyridin-3-yl2.3-F22-Bromacetyl
34882-chloropyridin-3-yl2.3-F22-Bromacetyl
34892-bromopyridin-3-yl2.3-F22-Bromacetyl
34902,6-difluoropyridin-3-yl2.3-F22-Bromacetyl
34915-chloro-6-fluoropyridin-3-yl2.3-F22-Bromacetyl
34925-bromo-6-fluoropyridin-3-yl2.3-F22-Bromacetyl
34935,6-difluoropyridin-3-yl2.3-F22-Bromacetyl
34946-chloro-5-fluoropyridin-3-yl2.3-F22-Bromacetyl
34956-bromo-5-fluoropyridin-3-yl2.3-F22-Bromacetyl
34964,5-difluoropyridin-3-yl2.3-F22-Bromacetyl
34974-chloro-5-fluoropyridin-3-yl2.3-F22-Bromacetyl
34984-bromo-5-fluoropyridin-3-yl2.3-F22-Bromacetyl
34995-chloro-4-fluoropyridin-3-yl2.3-F22-Bromacetyl
35004,5-dichloropyridin-3-yl2.3-F22-Bromacetyl
35014-bromo-5-chloropyridin-3-yl2.3-F22-Bromacetyl
35025-bromo-4-fluoropyridin-3-yl2.3-F22-Bromacetyl
35035-bromo-4-chloropyridin-3-yl2.3-F22-Bromacetyl
35044,5-dibromopyridin-3-yl2.3-F22-Bromacetyl
35052,5,6-trifluoropyridin-3-yl2.3-F22-Bromacetyl
35062-chloro-5,6-difluoropyridin-3-yl2.3-F22-Bromacetyl
35072-bromo-5,6-difluoropyridin-3-yl2.3-F22-Bromacetyl
35086-chloro-2,5-difluoropyridin-3-yl2.3-F22-Bromacetyl
35096-bromo-2,5-difluoropyridin-3-yl2.3-F22-Bromacetyl
35105-chloro-2,6-difluoropyridin-3-yl2.3-F22-Bromacetyl
35115-bromo-2,6-difluoropyridin-3-yl2.3-F22-Bromacetyl
35124,5,6-trifluoropyridin-3-yl2.3-F22-Bromacetyl
35134-chloro-5,6-difluoropyridin-3-yl2.3-F22-Bromacetyl
35144-bromo-5,6-difluoropyridin-3-yl2.3-F22-Bromacetyl
35155-chloro-4,6-difluoropyridin-3-yl2.3-F22-Bromacetyl
35165-bromo-4,6-difluoropyridin-3-yl2.3-F22-Bromacetyl
35176-chloro-4,5-difluoropyridin-3-yl2.3-F22-Bromacetyl
35186-bromo-4,5-difluoropyridin-3-yl2.3-F22-Bromacetyl
3519pyridin-3-yl2.3-F22-Bromacetyl
35206-fluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35216-chloropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35226-bromopyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35235-fluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35245-chloropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35255-bromopyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35264-fluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35274-chloropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35284-bromopyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35292-fluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35302-chloropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35312-bromopyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35322,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35335-chloro-6-fluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35345-bromo-6-fluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35355,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35366-chloro-5-fluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35376-bromo-5-fluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35384,5-difluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35394-chloro-5-fluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35404-bromo-5-fluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35415-chloro-4-fluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35424,5-dichloropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35434-bromo-5-chloropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35445-bromo-4-fluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35455-bromo-4-chloropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35464,5-dibromopyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35472,5,6-trifluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35482-chloro-5,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35492-bromo-5,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35506-chloro-2,5-difluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35516-bromo-2,5-difluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35525-chloro-2,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35535-bromo-2,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35544,5,6-trifluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35554-chloro-5,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35564-bromo-5,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35575-chloro-4,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35585-bromo-4,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35596-chloro-4,5-difluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35606-bromo-4,5-difluoropyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
3561pyridin-3-yl2.6-F2.4—Cl2-Bromacetyl
35626-fluoropyridin-3-yl2.3,6-F32-Bromacetyl
35636-chloropyridin-3-yl2.3,6-F32-Bromacetyl
35646-bromopyridin-3-yl2.3,6-F32-Bromacetyl
35655-fluoropyridin-3-yl2.3,6-F32-Bromacetyl
35665-chloropyridin-3-yl2.3,6-F32-Bromacetyl
35675-bromopyridin-3-yl2.3,6-F32-Bromacetyl
35684-fluoropyridin-3-yl2.3,6-F32-Bromacetyl
35694-chloropyridin-3-yl2.3,6-F32-Bromacetyl
35704-bromopyridin-3-yl2.3,6-F32-Bromacetyl
35712-fluoropyridin-3-yl2.3,6-F32-Bromacetyl
35722-chloropyridin-3-yl2.3,6-F32-Bromacetyl
35732-bromopyridin-3-yl2.3,6-F32-Bromacetyl
35742,6-difluoropyridin-3-yl2.3,6-F32-Bromacetyl
35755-chloro-6-fluoropyridin-3-yl2.3,6-F32-Bromacetyl
35765-bromo-6-fluoropyridin-3-yl2.3,6-F32-Bromacetyl
35775,6-difluoropyridin-3-yl2.3,6-F32-Bromacetyl
35786-chloro-5-fluoropyridin-3-yl2.3,6-F32-Bromacetyl
35796-bromo-5-fluoropyridin-3-yl2.3,6-F32-Bromacetyl
35804,5-difluoropyridin-3-yl2.3,6-F32-Bromacetyl
35814-chloro-5-fluoropyridin-3-yl2.3,6-F32-Bromacetyl
35824-bromo-5-fluoropyridin-3-yl2.3,6-F32-Bromacetyl
35835-chloro-4-fluoropyridin-3-yl2.3,6-F32-Bromacetyl
35844,5-dichloropyridin-3-yl2.3,6-F32-Bromacetyl
35854-bromo-5-chloropyridin-3-yl2.3,6-F32-Bromacetyl
35865-bromo-4-fluoropyridin-3-yl2.3,6-F32-Bromacetyl
35875-bromo-4-chloropyridin-3-yl2.3,6-F32-Bromacetyl
35884,5-dibromopyridin-3-yl2.3,6-F32-Bromacetyl
35892,5,6-trifluoropyridin-3-yl2.3,6-F32-Bromacetyl
35902-chloro-5,6-difluoropyridin-3-yl2.3,6-F32-Bromacetyl
35912-bromo-5,6-difluoropyridin-3-yl2.3,6-F32-Bromacetyl
35926-chloro-2,5-difluoropyridin-3-yl2.3,6-F32-Bromacetyl
35936-bromo-2,5-difluoropyridin-3-yl2.3,6-F32-Bromacetyl
35945-chloro-2,6-difluoropyridin-3-yl2.3,6-F32-Bromacetyl
35955-bromo-2,6-difluoropyridin-3-yl2.3,6-F32-Bromacetyl
35964,5,6-trifluoropyridin-3-yl2.3,6-F32-Bromacetyl
35974-chloro-5,6-difluoropyridin-3-yl2.3,6-F32-Bromacetyl
35984-bromo-5,6-difluoropyridin-3-yl2.3,6-F32-Bromacetyl
35995-chloro-4,6-difluoropyridin-3-yl2.3,6-F32-Bromacetyl
36005-bromo-4,6-difluoropyridin-3-yl2.3,6-F32-Bromacetyl
36016-chloro-4,5-difluoropyridin-3-yl2.3,6-F32-Bromacetyl
36026-bromo-4,5-difluoropyridin-3-yl2.3,6-F32-Bromacetyl
3603pyridin-3-yl2.3,6-F32-Bromacetyl
36046-fluoropyridin-3-yl2.3-F22-Methoxyacetyl
36056-chloropyridin-3-yl2.3-F22-Methoxyacetyl
36066-bromopyridin-3-yl2.3-F22-Methoxyacetyl
36075-fluoropyridin-3-yl2.3-F22-Methoxyacetyl
36085-chloropyridin-3-yl2.3-F22-Methoxyacetyl
36095-bromopyridin-3-yl2.3-F22-Methoxyacetyl
36104-fluoropyridin-3-yl2.3-F22-Methoxyacetyl
36114-chloropyridin-3-yl2.3-F22-Methoxyacetyl
36124-bromopyridin-3-yl2.3-F22-Methoxyacetyl
36132-fluoropyridin-3-yl2.3-F22-Methoxyacetyl
36142-chloropyridin-3-yl2.3-F22-Methoxyacetyl
36152-bromopyridin-3-yl2.3-F22-Methoxyacetyl
36162,6-difluoropyridin-3-yl2.3-F22-Methoxyacetyl
36175-chloro-6-fluoropyridin-3-yl2.3-F22-Methoxyacetyl
36185-bromo-6-fluoropyridin-3-yl2.3-F22-Methoxyacetyl
36195,6-difluoropyridin-3-yl2.3-F22-Methoxyacetyl
36206-chloro-5-fluoropyridin-3-yl2.3-F22-Methoxyacetyl
36216-bromo-5-fluoropyridin-3-yl2.3-F22-Methoxyacetyl
36224,5-difluoropyridin-3-yl2.3-F22-Methoxyacetyl
36234-chloro-5-fluoropyridin-3-yl2.3-F22-Methoxyacetyl
36244-bromo-5-fluoropyridin-3-yl2.3-F22-Methoxyacetyl
36255-chloro-4-fluoropyridin-3-yl2.3-F22-Methoxyacetyl
36264,5-dichloropyridin-3-yl2.3-F22-Methoxyacetyl
36274-bromo-5-chloropyridin-3-yl2.3-F22-Methoxyacetyl
36285-bromo-4-fluoropyridin-3-yl2.3-F22-Methoxyacetyl
36295-bromo-4-chloropyridin-3-yl2.3-F22-Methoxyacetyl
36304,5-dibromopyridin-3-yl2.3-F22-Methoxyacetyl
36312,5,6-trifluoropyridin-3-yl2.3-F22-Methoxyacetyl
36322-chloro-5,6-difluoropyridin-3-yl2.3-F22-Methoxyacetyl
36332-bromo-5,6-difluoropyridin-3-yl2.3-F22-Methoxyacetyl
36346-chloro-2,5-difluoropyridin-3-yl2.3-F22-Methoxyacetyl
36356-bromo-2,5-difluoropyridin-3-yl2.3-F22-Methoxyacetyl
36365-chloro-2,6-difluoropyridin-3-yl2.3-F22-Methoxyacetyl
36375-bromo-2,6-difluoropyridin-3-yl2.3-F22-Methoxyacetyl
36384,5,6-trifluoropyridin-3-yl2.3-F22-Methoxyacetyl
36394-chloro-5,6-difluoropyridin-3-yl2.3-F22-Methoxyacetyl
36404-bromo-5,6-difluoropyridin-3-yl2.3-F22-Methoxyacetyl
36415-chloro-4,6-difluoropyridin-3-yl2.3-F22-Methoxyacetyl
36425-bromo-4,6-difluoropyridin-3-yl2.3-F22-Methoxyacetyl
36436-chloro-4,5-difluoropyridin-3-yl2.3-F22-Methoxyacetyl
36446-bromo-4,5-difluoropyridin-3-yl2.3-F22-Methoxyacetyl
3645pyridin-3-yl2.3-F22-Methoxyacetyl
36466-fluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36476-chloropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36486-bromopyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36495-fluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36505-chloropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36515-bromopyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36524-fluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36534-chloropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36544-bromopyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36552-fluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36562-chloropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36572-bromopyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36582,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36595-chloro-6-fluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36605-bromo-6-fluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36615,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36626-chloro-5-fluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36636-bromo-5-fluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36644,5-difluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36654-chloro-5-fluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36664-bromo-5-fluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36675-chloro-4-fluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36684,5-dichloropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36694-bromo-5-chloropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36705-bromo-4-fluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36715-bromo-4-chloropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36724,5-dibromopyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36732,5,6-trifluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36742-chloro-5,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36752-bromo-5,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36766-chloro-2,5-difluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36776-bromo-2,5-difluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36785-chloro-2,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36795-bromo-2,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36804,5,6-trifluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36814-chloro-5,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36824-bromo-5,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36835-chloro-4,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36845-bromo-4,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36856-chloro-4,5-difluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36866-bromo-4,5-difluoropyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
3687pyridin-3-yl2.6-F2.4—Cl2-Methoxyacetyl
36886-fluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
36896-chloropyridin-3-yl2.3,6-F32-Methoxyacetyl
36906-bromopyridin-3-yl2.3,6-F32-Methoxyacetyl
36915-fluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
36925-chloropyridin-3-yl2.3,6-F32-Methoxyacetyl
36935-bromopyridin-3-yl2.3,6-F32-Methoxyacetyl
36944-fluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
36954-chloropyridin-3-yl2.3,6-F32-Methoxyacetyl
36964-bromopyridin-3-yl2.3,6-F32-Methoxyacetyl
36972-fluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
36982-chloropyridin-3-yl2.3,6-F32-Methoxyacetyl
36992-bromopyridin-3-yl2.3,6-F32-Methoxyacetyl
37002,6-difluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37015-chloro-6-fluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37025-bromo-6-fluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37035,6-difluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37046-chloro-5-fluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37056-bromo-5-fluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37064,5-difluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37074-chloro-5-fluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37084-bromo-5-fluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37095-chloro-4-fluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37104,5-dichloropyridin-3-yl2.3,6-F32-Methoxyacetyl
37114-bromo-5-chloropyridin-3-yl2.3,6-F32-Methoxyacetyl
37125-bromo-4-fluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37135-bromo-4-chloropyridin-3-yl2.3,6-F32-Methoxyacetyl
37144,5-dibromopyridin-3-yl2.3,6-F32-Methoxyacetyl
37152,5,6-trifluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37162-chloro-5,6-difluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37172-bromo-5,6-difluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37186-chloro-2,5-difluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37196-bromo-2,5-difluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37205-chloro-2,6-difluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37215-bromo-2,6-difluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37224,5,6-trifluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37234-chloro-5,6-difluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37244-bromo-5,6-difluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37255-chloro-4,6-difluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37265-bromo-4,6-difluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37276-chloro-4,5-difluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
37286-bromo-4,5-difluoropyridin-3-yl2.3,6-F32-Methoxyacetyl
3729pyridin-3-yl2.3,6-F32-Methoxyacetyl
37306-fluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37316-chloropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37326-bromopyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37335-fluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37345-chloropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37355-bromopyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37364-fluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37374-chloropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37384-bromopyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37392-fluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37402-chloropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37412-bromopyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37422,6-difluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37435-chloro-6-fluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37445-bromo-6-fluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37455,6-difluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37466-chloro-5-fluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37476-bromo-5-fluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37484,5-difluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37494-chloro-5-fluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37504-bromo-5-fluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37515-chloro-4-fluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37524,5-dichloropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37534-bromo-5-chloropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37545-bromo-4-fluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37555-bromo-4-chloropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37564,5-dibromopyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37572,5,6-trifluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37582-chloro-5,6-difluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37592-bromo-5,6-difluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37606-chloro-2,5-difluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37616-bromo-2,5-difluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37625-chloro-2,6-difluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37635-bromo-2,6-difluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37644,5,6-trifluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37654-chloro-5,6-difluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37664-bromo-5,6-difluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37675-chloro-4,6-difluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37685-bromo-4,6-difluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37696-chloro-4,5-difluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37706-bromo-4,5-difluoropyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
3771pyridin-3-yl2.3-F2C(O)CH2C(O)OCH3
37726-fluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37736-chloropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37746-bromopyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37755-fluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37765-chloropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37775-bromopyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37784-fluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37794-chloropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37804-bromopyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37812-fluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37822-chloropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37832-bromopyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37842,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37855-chloro-6-fluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37865-bromo-6-fluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37875,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37886-chloro-5-fluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37896-bromo-5-fluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37904,5-difluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37914-chloro-5-fluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37924-bromo-5-fluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37935-chloro-4-fluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37944,5-dichloropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37954-bromo-5-chloropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37965-bromo-4-fluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37975-bromo-4-chloropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37984,5-dibromopyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
37992,5,6-trifluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
38002-chloro-5,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
38012-bromo-5,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
38026-chloro-2,5-difluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
38036-bromo-2,5-difluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
38045-chloro-2,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
38055-bromo-2,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
38064,5,6-trifluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
38074-chloro-5,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
38084-bromo-5,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
38095-chloro-4,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
38105-bromo-4,6-difluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
38116-chloro-4,5-difluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
38126-bromo-4,5-difluoropyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
3813pyridin-3-yl2.6-F2.4—ClC(O)CH2C(O)OCH3
38146-fluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38156-chloropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38166-bromopyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38175-fluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38185-chloropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38195-bromopyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38204-fluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38214-chloropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38224-bromopyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38232-fluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38242-chloropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38252-bromopyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38262,6-difluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38275-chloro-6-fluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38285-bromo-6-fluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38295,6-difluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38306-chloro-5-fluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38316-bromo-5-fluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38324,5-difluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38334-chloro-5-fluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38344-bromo-5-fluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38355-chloro-4-fluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38364,5-dichloropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38374-bromo-5-chloropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38385-bromo-4-fluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38395-bromo-4-chloropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38404,5-dibromopyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38412,5,6-trifluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38422-chloro-5,6-difluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38432-bromo-5,6-difluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38446-chloro-2,5-difluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38456-bromo-2,5-difluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38465-chloro-2,6-difluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38475-bromo-2,6-difluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38484,5,6-trifluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38494-chloro-5,6-difluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38504-bromo-5,6-difluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38515-chloro-4,6-difluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38525-bromo-4,6-difluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38536-chloro-4,5-difluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38546-bromo-4,5-difluoropyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
3855pyridin-3-yl2.3,6-F3C(O)CH2C(O)OCH3
38566-fluoropyridin-3-yl2.3-F22-Chloracetyl
38576-chloropyridin-3-yl2.3-F22-Chloracetyl
38586-bromopyridin-3-yl2.3-F22-Chloracetyl
38595-fluoropyridin-3-yl2.3-F22-Chloracetyl
38605-chloropyridin-3-yl2.3-F22-Chloracetyl
38615-bromopyridin-3-yl2.3-F22-Chloracetyl
38624-fluoropyridin-3-yl2.3-F22-Chloracetyl
38634-chloropyridin-3-yl2.3-F22-Chloracetyl
38644-bromopyridin-3-yl2.3-F22-Chloracetyl
38652-fluoropyridin-3-yl2.3-F22-Chloracetyl
38662-chloropyridin-3-yl2.3-F22-Chloracetyl
38672-bromopyridin-3-yl2.3-F22-Chloracetyl
38682,6-difluoropyridin-3-yl2.3-F22-Chloracetyl
38695-chloro-6-fluoropyridin-3-yl2.3-F22-Chloracetyl
38705-bromo-6-fluoropyridin-3-yl2.3-F22-Chloracetyl
38715,6-difluoropyridin-3-yl2.3-F22-Chloracetyl
38726-chloro-5-fluoropyridin-3-yl2.3-F22-Chloracetyl
38736-bromo-5-fluoropyridin-3-yl2.3-F22-Chloracetyl
38744,5-difluoropyridin-3-yl2.3-F22-Chloracetyl
38754-chloro-5-fluoropyridin-3-yl2.3-F22-Chloracetyl
38764-bromo-5-fluoropyridin-3-yl2.3-F22-Chloracetyl
38775-chloro-4-fluoropyridin-3-yl2.3-F22-Chloracetyl
38784,5-dichloropyridin-3-yl2.3-F22-Chloracetyl
38794-bromo-5-chloropyridin-3-yl2.3-F22-Chloracetyl
38805-bromo-4-fluoropyridin-3-yl2.3-F22-Chloracetyl
38815-bromo-4-chloropyridin-3-yl2.3-F22-Chloracetyl
38824,5-dibromopyridin-3-yl2.3-F22-Chloracetyl
38832,5,6-trifluoropyridin-3-yl2.3-F22-Chloracetyl
38842-chloro-5,6-difluoropyridin-3-yl2.3-F22-Chloracetyl
38852-bromo-5,6-difluoropyridin-3-yl2.3-F22-Chloracetyl
38866-chloro-2,5-difluoropyridin-3-yl2.3-F22-Chloracetyl
38876-bromo-2,5-difluoropyridin-3-yl2.3-F22-Chloracetyl
38885-chloro-2,6-difluoropyridin-3-yl2.3-F22-Chloracetyl
38895-bromo-2,6-difluoropyridin-3-yl2.3-F22-Chloracetyl
38904,5,6-trifluoropyridin-3-yl2.3-F22-Chloracetyl
38914-chloro-5,6-difluoropyridin-3-yl2.3-F22-Chloracetyl
38924-bromo-5,6-difluoropyridin-3-yl2.3-F22-Chloracetyl
38935-chloro-4,6-difluoropyridin-3-yl2.3-F22-Chloracetyl
38945-bromo-4,6-difluoropyridin-3-yl2.3-F22-Chloracetyl
38956-chloro-4,5-difluoropyridin-3-yl2.3-F22-Chloracetyl
38966-bromo-4,5-difluoropyridin-3-yl2.3-F22-Chloracetyl
3897pyridin-3-yl2.3-F22-Chloracetyl
38986-fluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
38996-chloropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39006-bromopyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39015-fluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39025-chloropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39035-bromopyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39044-fluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39054-chloropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39064-bromopyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39072-fluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39082-chloropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39092-bromopyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39102,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39115-chloro-6-fluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39125-bromo-6-fluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39135,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39146-chloro-5-fluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39156-bromo-5-fluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39164,5-difluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39174-chloro-5-fluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39184-bromo-5-fluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39195-chloro-4-fluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39204,5-dichloropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39214-bromo-5-chloropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39225-bromo-4-fluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39235-bromo-4-chloropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39244,5-dibromopyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39252,5,6-trifluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39262-chloro-5,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39272-bromo-5,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39286-chloro-2,5-difluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39296-bromo-2,5-difluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39305-chloro-2,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39315-bromo-2,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39324,5,6-trifluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39334-chloro-5,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39344-bromo-5,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39355-chloro-4,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39365-bromo-4,6-difluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39376-chloro-4,5-difluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39386-bromo-4,5-difluoropyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
3939pyridin-3-yl2.6-F2.4—Cl2-Chloracetyl
39406-fluoropyridin-3-yl2.3,6-F32-Chloracetyl
39416-chloropyridin-3-yl2.3,6-F32-Chloracetyl
39426-bromopyridin-3-yl2.3,6-F32-Chloracetyl
39435-fluoropyridin-3-yl2.3,6-F32-Chloracetyl
39445-chloropyridin-3-yl2.3,6-F32-Chloracetyl
39455-bromopyridin-3-yl2.3,6-F32-Chloracetyl
39464-fluoropyridin-3-yl2.3,6-F32-Chloracetyl
39474-chloropyridin-3-yl2.3,6-F32-Chloracetyl
39484-bromopyridin-3-yl2.3,6-F32-Chloracetyl
39492-fluoropyridin-3-yl2.3,6-F32-Chloracetyl
39502-chloropyridin-3-yl2.3,6-F32-Chloracetyl
39512-bromopyridin-3-yl2.3,6-F32-Chloracetyl
39522,6-difluoropyridin-3-yl2.3,6-F32-Chloracetyl
39535-chloro-6-fluoropyridin-3-yl2.3,6-F32-Chloracetyl
39545-bromo-6-fluoropyridin-3-yl2.3,6-F32-Chloracetyl
39555,6-difluoropyridin-3-yl2.3,6-F32-Chloracetyl
39566-chloro-5-fluoropyridin-3-yl2.3,6-F32-Chloracetyl
39576-bromo-5-fluoropyridin-3-yl2.3,6-F32-Chloracetyl
39584,5-difluoropyridin-3-yl2.3,6-F32-Chloracetyl
39594-chloro-5-fluoropyridin-3-yl2.3,6-F32-Chloracetyl
39604-bromo-5-fluoropyridin-3-yl2.3,6-F32-Chloracetyl
39615-chloro-4-fluoropyridin-3-yl2.3,6-F32-Chloracetyl
39624,5-dichloropyridin-3-yl2.3,6-F32-Chloracetyl
39634-bromo-5-chloropyridin-3-yl2.3,6-F32-Chloracetyl
39645-bromo-4-fluoropyridin-3-yl2.3,6-F32-Chloracetyl
39655-bromo-4-chloropyridin-3-yl2.3,6-F32-Chloracetyl
39664,5-dibromopyridin-3-yl2.3,6-F32-Chloracetyl
39672,5,6-trifluoropyridin-3-yl2.3,6-F32-Chloracetyl
39682-chloro-5,6-difluoropyridin-3-yl2.3,6-F32-Chloracetyl
39692-bromo-5,6-difluoropyridin-3-yl2.3,6-F32-Chloracetyl
39706-chloro-2,5-difluoropyridin-3-yl2.3,6-F32-Chloracetyl
39716-bromo-2,5-difluoropyridin-3-yl2.3,6-F32-Chloracetyl
39725-chloro-2,6-difluoropyridin-3-yl2.3,6-F32-Chloracetyl
39735-bromo-2,6-difluoropyridin-3-yl2.3,6-F32-Chloracetyl
39744,5,6-trifluoropyridin-3-yl2.3,6-F32-Chloracetyl
39754-chloro-5,6-difluoropyridin-3-yl2.3,6-F32-Chloracetyl
39764-bromo-5,6-difluoropyridin-3-yl2.3,6-F32-Chloracetyl
39775-chloro-4,6-difluoropyridin-3-yl2.3,6-F32-Chloracetyl
39785-bromo-4,6-difluoropyridin-3-yl2.3,6-F32-Chloracetyl
39796-chloro-4,5-difluoropyridin-3-yl2.3,6-F32-Chloracetyl
39806-bromo-4,5-difluoropyridin-3-yl2.3,6-F32-Chloracetyl
3981pyridin-3-yl2.3,6-F32-Chloracetyl

[0197]

Likewise preferred compounds of the formula (I) or (Ia) according to the invention are described in the Example section below.

[0198]

For preferred compounds of the formula (I) or (Ia) according to the invention, m is greater than or equal to 1, preferably greater than or equal to 2, and the following applies:

[0199]

one, more than one or all radicals R2are selected from the group consisting of F, Cl, Br, I, methyl and CN,

[0000]

and
one, more than one or all radicals R3are selected from the group consisting of F, Cl, Br, methyl, methoxy, nitro and CN.

[0200]

For preferred compounds of the formula (I) or (Ia) according to the invention, the following applies:

[0000]

n is greater than or equal to 1, preferably greater than or equal to 2,
m is greater than or equal to 1, preferably greater than or equal to 2,
one, more than one or all radicals R2are selected from the group consisting of F, Cl, Br, I, methyl and CN,
and
one, more than one or all radicals R3are selected from the group consisting of F, Cl, Br, methyl, methoxy and CN.

[0201]

Particular preference according to the invention is given to compounds of the formula (I) or (Ia) or salts thereof where the following applies:

[0000]

n=1, 2 or 3, and at least one R2is selected, preferably all R2are selected, from the group consisting of fluorine, chlorine and bromine,
and/or
m=1, 2 or 3, and at least one R3is selected, preferably all R3are selected, from the group consisting of fluorine and chlorine.

[0202]

Likewise preferred according to the invention are compounds of the formula (I) and/or salts thereof in which (R3)mis 3-chloro, 4-chloro, 2,3-dichloro, 2,4-dichloro, 2,5-dichloro, 2,6-dichloro, 3,4-dichloro, 3,5-dichloro, 2-fluoro, 3-fluoro, 4-fluoro, 2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, 2,3,6-trifluoro, 2,4,6-trifluoro, (3-Cl-2-F), (3-Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F), (4-Cl-3-F) or (2,6-F2-4-Cl).

[0203]

Likewise preferred according to the invention are compounds of the formula (Ia) and/or salts thereof in which (R3)mis 3-chloro, 4-chloro, 2,3-dichloro, 2,4-dichloro, 2,5-dichloro, 2,6-dichloro, 3,4-dichloro, 3,5-dichloro, 2-fluoro, 3-fluoro, 4-fluoro, 2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, 2,3,6-trifluoro, 2,4,6-trifluoro, (3-Cl-2-F), (3-Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F), (4-Cl-3-F) or (2,6-F2-4-Cl).

[0204]

Among the compounds according to the invention with the meanings given above, preference is given to those in which the structural element Q, R′, (R2)nand (R3)mdefined in each case as preferred, in each case as particularly preferred or in each case as especially preferred are realized in combination with one another.

[0205]

The compounds of the formula (I) according to the invention can have (2,3)-erythro configuration, i.e. correspond to the compounds of the following formulae (I eryrthro-1) and (I eryrthro-2):

[0000]

[0206]

Furthermore, it has been found that the compounds of the formula (I) according to the invention and/or their salts or (Ia) and/or their salts which are (2,3)-threo-configured have better herbicidal properties than the corresponding (2,3)-erythro-configured compounds. Accordingly, (2,3)-threo-configured compounds of the formulae (I) and (Ia) and their salts are preferred. The same applies accordingly to compositions according to the invention.

[0207]

Accordingly, preference according to the invention is given to mixtures and compositions in which the molar ratio of a (2,3)-threo-configured compound of the formula (I) to the corresponding (2,3)-erythro-configured compound of the formula (I) is greater than 1, more preferably greater than 2, particularly preferably greater than 3 and especially preferably greater than 4.

[0208]

Likewise, preference according to the invention is given to mixtures and compositions in which the weight ratio of the total amount of (2,3)-threo-configured compounds of the formulae (I) and (Ia) to the total amount of (2,3)-erythro-configured compounds of the formulae (I) and (Ia) is greater than 1, more preferably greater than 2, particularly preferably greater than 3 and especially preferably greater than 4.

[0209]

Surprisingly, it has furthermore been found that optically active threo-configured compounds of the formula (I) and their salts have particularly good herbicidal activities and at the same time advantageous selectivities with respect to some useful plants.

[0210]

Accordingly, in the context of the present invention preference is given to compounds of the formula (I) and their salts having a (2,3)-threo-configuration, i.e. compounds of the following formulae (I threo-1) and (I threo-2)

[0000]

[0000]

in which
R1, R2, R3, n and m each have the meaning mentioned above, preferably one of the meanings given in each case as being preferred or particularly preferred.

[0211]

In the context of the present invention preference is given to compounds of the formula (Ia) and their salts having a (2,3)-threo-configuration, i.e. compounds of the following formulae (Ia threo-1) and/or (Ia threo-2)

[0000]

[0000]

in which
R2, R3, n and m each have the meaning mentioned above, preferably one of the meanings given in each case as being preferred or particularly preferred or especially preferred.

[0212]

The stereochemical configuration at the carbon atom in position 2 of the pentanonitrile derivative of the formulae (I) and (Ia) preferably has a stereochemical purity of from 60 to 100% (S), with preference from 70 to 100% (S), more preferably from 80 to 100% (S), especially preferably from 90 to 100% (S), and the stereochemical configuration at the carbon atom in position 3 of the pentanonitrile derivative preferably has a stereochemical purity of from 60 to 100% (5), with preference from 70 to 100% (S), more preferably from 80 to 100% (S), especially preferably from 90 to 100% (S), in each case based on the total amount of the threo-enantiomers in question.

[0213]

The stereochemical configuration at the carbon atom in position 2 of the pentanonitrile derivative of the formulae (I) and (Ia) preferably has a stereochemical purity of from 60 to 100% (R), with preference from 70 to 100% (R), more preferably from 80 to 100% (R), especially preferably from 90 to 100% (R), and the stereochemical configuration at the carbon atom in position 3 of the pentanonitrile derivative preferably has a stereochemical purity of from 60 to 100% (R), with preference from 70 to 100% (R), more preferably from 80 to 100% (R), especially preferably from 90 to 100% (R), in each case based on the total amount of the threo-enantiomers in question.

[0214]

By virtue of their even better property profile, in particular their even better herbicidal activity, special preference is given to the (2R,3R)-configured pentanonitrile derivatives of the formulae (I) and (Ia), preferably in the stereochemical purities stated above. As a consequence, compounds of the formulae (I threo-1) and (Ia threo-1) are particularly preferred in the context of the present invention. The absolute configuration of these (2R,3R)-configured pentanonitrile derivatives was assigned by X-ray structural analysis.

[0215]

That stated above applies accordingly to mixtures according to the invention and compositions according to the invention.

[0216]

The compounds of the formula (I) according to the invention can be prepared by various processes.

[0217]

In the processes described below, in some cases solvents are employed. In this context, “inert solvents” refers in each case to solvents which are inert under the particular reaction conditions, but which do not have to be inert under any reaction conditions. In the processes below, the reactions described can alternatively also be carried out in a microwave reactor.

[0218]

The compounds according to the invention can be prepared by methods known per se. Here, the starting material may, for example, be compounds of the formula (E). Compounds of the formula (E) are known from the prior art, for example from WO 2013/092500 A1. The scheme below shows, in an exemplary manner, how the compounds according to the invention can be prepared.

[0000]

[0219]

Here, R1, R2, R3, n and m each have the (preferred or particularly preferred) meaning mentioned above, and R represents hydrogen or an organic radical, preferably a radical selected from the group of the radicals defined above for R1.

[0220]

With respect to “Step 1” of the above scheme:

[0221]

Methods for the selective reduction of compounds of the formula (E) to give corresponding compounds of the formula (Ia) are known to the person skilled in the art from the prior art and described, for example, in European Journal of Organic Chemistry 2009, (11), 1806-1811 or in WO 2012/076513 A1. Preferably, the selective reduction in this case is carried out using borohydrides, with preference using borohydrides of alkali metal borohydrides, in particular of lithium borohydride, sodium borohydride or potassium borohydride, and in turn preferably in the presence of a lithium halide, preferably in the presence of lithium chloride. Here, this reduction can be carried out in a protic organic solvent such as, for example, ethanol (see, for example, WO 2011/014383), or an aprotic organic solvent such as, for example, tetrahydrofuran (THF), here preferably by heating under reflux.

[0222]

With respect to “Step 2” of the above scheme:

[0223]

The present optional further reaction (nucleophilic substitution) of the primary alcohol (Ia) obtained in “Step 1” with R1—X1(where X1represents a leaving group) to give compounds of the formula (I) is known in principle to the person skilled in the art and described, for example, in Journal of Organic Chemistry 2011, 76(3), 811-819. Here, the nucleophilic substitution is preferably carried out in the presence of 4-(dimethylamino)pyridine. The reaction can also be carried out, for example, in an aprotic organic solvent such as tetrahydrofuran (THF) or dichloromethane, if appropriate at elevated temperature, for example by heating under reflux.

[0224]

Accordingly, the present invention also relates to a process for preparing a compound of the formula (I) according to the invention and/or a salt thereof, characterized in that a compound of the formula (E)

[0000]

[0000]

is converted by reduction into a compound of the formula (Ia)

[0000]

[0000]

and the compound (Ia) is optionally reacted further to give a compound of the formula (I), provided R1does not represent hydrogen,
where
R represents hydrogen or an organic radical, preferably a radical selected from the group of the radicals defined above for R1, with preference selected from one of the radicals characterized as being preferred,
and
R2, R3, m and n each have the meaning defined above, and are preferably in each case selected from one of the groups of radicals characterized as being preferred.

[0225]

The starting materials (E) used for preparing the compounds of the formula (Ia) or (I) are known from the literature cited or can be prepared analogously to the literature cited.

[0226]

To prepare the compounds (Ia) or (I) according to the invention, it is also possible to use the corresponding diastereomer mixtures in the form of their racemic mixtures.

[0227]

If stereochemically enriched compounds of the formula (E) mentioned above are used in the process according to the invention, it is possible to obtain the corresponding stereochemically enriched compounds of the formula (Ia) or (I).

[0228]

Solvents suitable for this purpose are, for example, organic solvents such as:

    • aliphatic hydrocarbons such as pentane, hexane, cyclohexane or petroleum ether;
    • aromatic hydrocarbons such as toluene, o-, m- or p-xylene,
    • halogenated hydrocarbons such as methylene chloride, chloroform or chlorobenzene,
    • ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and
    • tetrahydrofuran (THF),
    • nitriles such as acetonitrile or propionitrile,
    • ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone,
    • dimethyl sulfoxide, dimethylformamide, dimethylacetamide, sulfolane, and also
    • mixtures of the stated organic solvents.

[0238]

In individual cases, it is also appropriate to use inorganic solvents such as water or mixtures of organic solvents with water.

[0239]

Suitable conditions and catalysts for the preparation of compounds of the formula (I) in which R1does not represent H from compounds of the formula (Ia), for example by esterification, are known to the person skilled in the art.

[0240]

The conversion of compounds of the formula (Ia) into compounds of the formula (I) in which R1does not represent H can be carried out in the presence of a base, for example a base from the group of the inorganic bases such as the alkali metal and alkaline earth metal hydroxides, for example lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, the alkali metal and alkaline earth metal oxides, for example lithium oxide, sodium oxide, calcium oxide or magnesium oxide, the alkali metal and alkaline earth metal hydrides, for example lithium hydride, sodium hydride, potassium hydride or calcium hydride, the alkali metal amides, for example lithium amide, sodium amide or potassium amide, the alkali metal and alkaline earth metal carbonates, for example lithium carbonate, potassium carbonate or calcium carbonate, the alkali metal bicarbonates, for example sodium bicarbonate, or the organometallic compounds such as, preferably, the alkali metal alkyls, for example methyllithium, butyllithium or phenyllithium, the alkylmagnesium halides, for example methylmagnesium chloride, or the alkali metal and alkaline earth metal alkoxides, for example sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide or dimethoxymagnesium.

[0241]

The bases used can also be organic bases, for example from the group of the tertiary aliphatic amines, for example trimethylamine, triethylamine, tributylamine, diisopropylethylamine or N-methylpiperidine, or the aromatic tertiary amines, for example pyridine or substituted pyridines such as collidine, lutidine or 4-dimethylaminopyridine, or the bicyclic amines such as 7-methyl-1,5,7-triazabicyclo[4.4.0]-dec-5-ene or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

[0242]

Preferred bases are, for example, lithium hydroxide, potassium carbonate, potassium tert-butoxide, lithium bis(trimethylsilyl)amide, pyridines, substituted pyridines, 7-methyl-1,5, 7-triazabicyclo[4.4.0]-dec-5-ene or DBU.

[0243]

The amount of base may generally vary within wide limits. For example, it may be expedient to employ the base in catalytic amounts, in substoichiometric amounts, in equimolar amounts or in excess. A preferably liquid organic base may optionally also be used as solvent.

[0244]

Suitable catalysts for the conversion of compounds of the formula (Ia) into compounds of the formula (I) in which R1is not H may also be acidic catalysts, for example from the group of the inorganic acids, for example Broensted acids, such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acid or perchloric acid, or Lewis acids, such as boron trifluoride, aluminum trichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chloride, scandium(III) triflate or zinc(II) chloride, and also organic acids, for example formic acid, acetic acid, propionic acid, oxalic acid, toluenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid or trifluoroacetic acid.

[0245]

The reaction mixtures obtained are worked up in a customary manner, for example by mixing with water, separating the phases and optionally chromatographic purification of the crude products. Some of the compounds are obtained in the form of colorless or slightly brownish viscous oils which are purified or freed from volatile components under reduced pressure and at moderately elevated temperature.

[0246]

If the compounds are obtained as solids, the purification can also be carried out by recrystallization or digestion. If individual compounds (I) cannot be obtained in a satisfactory manner by the routes described above, they can be prepared by derivatization of other compounds (I) or (Ia).

[0247]

Suitable isolation methods, purification methods and methods for separating stereoisomers of compounds of the formula (I) or (Ia) are methods generally known to the person skilled in the art from analogous cases, for example by physical processes such as crystallization, chromatographic methods, in particular column chromatography and HPLC (high pressure liquid chromatography), distillation, optionally under reduced pressure, extraction and other methods, any mixtures that remain can generally be separated by chromatographic separation, for example on chiral solid phases. Suitable for preparative amounts or on an industrial scale are processes such as crystallization, for example of diastereomeric salts which can be obtained from the diastereomer mixtures using optically active acids and, if appropriate, provided that acidic groups are present, using optically active bases.

[0248]

Optically active acids which are suitable for optical resolution by crystallization of diastereomeric salts are, for example, camphorsulfonic acid, camphoric acid, bromocamphorsulfonic acid, quinic acid, tartaric acid, dibenzoyltartaric acid and other analogous acids; suitable optically active bases are, for example, quinine, cinchonine, quinidine, brucine, 1-(S)- or 1-(R)-phenylethylamine and other analogous bases.

[0249]

The crystallizations are then in most cases carried out in aqueous, alcoholic or aqueous-organic solvents, where the diastereomer which is less soluble precipitates first, if appropriate after seeding. One enantiomer of the compound of the formula (I) is then liberated from the precipitated salt, or the other is liberated from the crystallizate, by acidification or using a base.

[0250]

As an alternative to the optical resolution methods mentioned, enantioselective processes starting with stereochemically pure starting materials are in principle also suitable for preparing the (threo) enantiomers.

[0251]

The following acids are generally suitable for preparing the acid addition salts of the compounds of the formula (I): hydrohalic acids, such as hydrochloric acid or hydrobromic acid, furthermore phosphoric acid, nitric acid, sulfuric acid, mono- or bifunctional carboxylic acids and hydroxycarboxylic acids, such as acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid, or lactic acid, and also sulfonic acids, such as p-toluenesulfonic acid and 1,5-naphthalenedisulfonic acid. The acid addition compounds of the formula (I) can be obtained in a manner known per se by the customary methods for forming salts, for example by dissolving a compound of the formula (I) in a suitable organic solvent, such as, for example, methanol, acetone, methylene chloride or benzene, and adding the acid at temperatures of from 0 to 100° C., and they can be isolated in a known manner, for example by filtration, and, if appropriate, purified by washing with an inert organic solvent.

[0252]

Base addition salts of the compounds of the formula (I) can be prepared, for example, in polar solvents such as, for example, water, methanol or acetone, at temperatures of from 0 to 100° C. Examples of bases which are suitable for the preparation of such salts are, for example, alkali metal carbonates, such as potassium carbonate, alkali metal hydroxides and alkaline earth metal hydroxides, for example NaOH or KOH, alkali metal hydrides and alkaline earth metal hydrides, for example NaH, alkali metal alkoxides and alkaline earth metal alkoxides, for example sodium methoxide or potassium tert-butoxide, or ammonia, ethanolamine or quaternary ammonium hydroxide.

[0253]

A collection of compounds of the formula (I) can additionally be prepared in a parallel or combinatorial manner, it being possible for this to take place in a manual, partly automated or completely automated manner. In this connection, it is possible to automate the reaction procedure, the work-up or the purification of the products and/or intermediates.

[0254]

For the parallelized reaction procedure and work-up it is possible to use a range of commercially available instruments, of the kind offered by, for example, the companies Stem Corporation, Woodrolfe Road, Tollesbury, Essex, CM9 8SE, England, or H+P Labortechnik GmbH, Bruckmannring 28, 85764 Oberschleiβheim, Germany. For the parallelized purification of compounds (I) or of intermediates produced during the preparation, there are available, inter alia, chromatography apparatuses, for example from ISCO, Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA. The apparatuses listed allow a modular procedure in which the individual process steps are automated, but between the process steps manual operations have to be carried out. This can be circumvented by using partly or completely integrated automation systems in which the respective automation modules are operated, for example, by robots. Automation systems of this type can be acquired, for example, from Zymark Corporation, Zymark Center, Hopkinton, Mass. 01748, USA.

[0255]

Besides the methods described, the preparation of compounds of the formula (I) can take place completely or partially by solid-phase-supported methods. For this purpose, individual intermediates or all intermediates in the synthesis or a synthesis adapted for the corresponding procedure are bonded to a synthesis resin. Solid-phase-supported synthesis methods are described extensively in the specialist literature, for example: Barry A. Bunin in “The Combinatorial Index”, Verlag Academic Press, 1998.

[0256]

The use of solid-phase-supported synthesis methods permits a number of protocols, which are known from the literature and which for their part may be performed manually or in an automated manner. For example, the so-called “tea bag method” (U.S. Pat. No. 4,631,211) in which products from IRORI, 11149 North Torrey Pines Road, La Jolla, Calif. 92037, USA, are employed, may be semiautomated. The automation of solid-phase-supported parallel syntheses is performed successfully, for example, by apparatuses from Argonaut Technologies, Inc., 887 Industrial Road, San Carlos, Calif. 94070, USA or MultiSynTech GmbH, Wullener Feld 4, 58454 Witten, Germany.

[0257]

The preparation according to the processes described herein produces compounds of the formula (I) in the form of substance collections or libraries. Accordingly, the present invention also provides libraries of compounds of the formula (I) which comprise at least two compounds of the formula (I), and precursors thereof.

[0258]

The present invention furthermore provides a method for controlling harmful plants and/or for regulating the growth of plants, characterized in that an effective amount

    • of one or more compounds of the formula (I) and/or salts thereof, as defined above,
    • of one or more compounds of the formula (Ia) and/or salts thereof, as defined above,
      or
    • of a composition, as defined above,
      is applied to the (harmful) plants, seeds of (harmful) plants, the soil in which or on which the (harmful) plants grow or the area under cultivation.

[0262]

The present invention also provides a method for controlling unwanted plants, preferably in crops of useful plants, characterized in that an effective amount

    • of one or more compounds of the formula (I) and/or salts thereof, as defined above,
    • of one or more compounds of the formula (Ia) and/or salts thereof, as defined above, or
    • of a composition according to the invention, as defined above,
      is applied to unwanted plants (for example harmful plants such as mono- or dicotyledonous weeds or unwanted crop plants), the seed of the unwanted plants (i.e. plant seeds, for example grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in which or on which the unwanted plants grow (for example the soil of crop land or non-crop land) or the area under cultivation (i.e. the area on which the unwanted plants will grow).

[0266]

The present invention furthermore also provides methods for regulating the growth of plants, preferably of useful plants, characterized in that an effective amount

    • of one or more compounds of the formula (I) and/or salts thereof, as defined above,
    • of one or more compounds of the formula (Ia) and/or salts thereof, as defined above, or
    • of a composition according to the invention, as defined above,
      is applied to the plant, the seed of the plant (i.e. plant seed, for example grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in which or on which the plants grow (for example the soil of crop land or non-crop land) or the area under cultivation (i.e. the area on which the plants will grow).

[0270]

In this context, the compounds according to the invention or the compositions according to the invention can be applied for example by pre-sowing (if appropriate also by incorporation into the soil), pre-emergence and/or post-emergence processes. Specific examples of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds of the invention are as follows, though there is no intention to restrict the enumeration to particular species.

[0271]

In a method according to the invention for controlling harmful plants or for regulating the growth of plants, one or more compounds of the formula (I), (Ia) and/or salts thereof are preferably employed for controlling harmful plants or for regulating growth in crops of useful plants or ornamental plants, where in a preferred embodiment the useful plants or ornamental plants are transgenic plants.

[0272]

The compounds of the formula (I) or (Ia) according to the invention and/or their salts are suitable for controlling the following genera of monocotyledonous and dicotyledonous harmful plants:

[0273]

Monocotyledonous Harmful Plants of the Genera:

[0274]

Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria and Sorghum.

[0275]

Dicotyledonous Harmful Plants of the Genera:

[0276]

Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola and Xanthium.

[0277]

When the compounds according to the invention are applied to the soil surface before germination of the harmful plants (weed grasses and/or broad-leaved weeds) (pre-emergence method), either the seedlings of the weed grasses or broad-leaved weeds are prevented completely from emerging or they grow until they have reached the cotyledon stage, but then stop growing and eventually, after three to four weeks have elapsed, die completely.

[0278]

If the active ingredients are applied post-emergence to the green parts of the plants, growth stops after the treatment, and the harmful plants remain at the growth stage at the time of application, or they die completely after a certain time, such that competition by the weeds, which is harmful to the crop plants, is thus eliminated very early and in a lasting manner.

[0279]

Although the compounds according to the invention display an outstanding herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, for example dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, triticale, triticum, Zea, are damaged only to an insignificant extent, or not at all, depending on the structure of the respective compound according to the invention and its application rate. For these reasons, the present compounds are very suitable for selective control of unwanted plant growth in plant crops such as agriculturally useful plants or ornamental plants.

[0280]

In addition, the compounds according to the invention (depending on their particular structure and the application rate deployed) have outstanding growth-regulating properties in crop plants. They intervene in the plants' own metabolism with regulatory effect, and can thus be used for the controlled influencing of plant constituents and to facilitate harvesting, for example by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth without killing the plants in the process. Inhibition of vegetative growth plays a major role for many mono- and dicotyledonous crops since, for example, this can reduce or completely prevent lodging.

[0281]

By virtue of their herbicidal and plant growth regulatory properties, the active ingredients can also be used to control harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis. In general, the transgenic plants are characterized by particular advantageous properties, for example by resistances to certain pesticides, in particular certain herbicides, resistances to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific characteristics relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or those with a different fatty acid composition in the harvested material.

[0282]

It is preferred with a view to transgenic crops to use the compounds according to the invention and/or their salts in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, millet, rice and maize or else crops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas and other vegetables.

[0283]

It is preferred to employ the compounds according to the invention as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

[0284]

By virtue of their herbicidal and plant growth regulatory properties, the active ingredients can also be used to control harmful plants in crops of genetically modified plants which are known or are yet to be developed. In general, the transgenic plants are characterized by particular advantageous properties, for example by resistances to certain pesticides, in particular certain herbicides, resistances to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific characteristics relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or those with a different fatty acid composition in the harvested material. Further special properties may be tolerance or resistance to abiotic stressors, for example heat, cold, drought, salinity and ultraviolet radiation.

[0285]

Preference is given to the use of the compounds of the formula (I) according to the invention or salts thereof in economically important transgenic crops of useful plants and ornamental plants, for example of cereals such as wheat, barley, rye, oats, triticale, millet, rice, cassava and corn, or else crops of sugar beet, cotton, soybean, oilseed rape, potatoes, tomatoes, peas and other vegetables.

[0286]

The compounds of the formula (I) can preferably be used as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

[0287]

Conventional ways of producing novel plants which have modified properties in comparison to existing plants consist, for example, in traditional cultivation methods and the generation of mutants. Alternatively, novel plants with altered properties can be generated with the aid of recombinant methods.

[0288]

A large number of molecular-biological techniques by means of which novel transgenic plants with modified properties can be generated are known to the person skilled in the art. For such recombinant manipulations, nucleic acid molecules which allow mutagenesis or sequence alteration by recombination of DNA sequences can be introduced into plasmids. With the aid of standard methods, it is possible, for example, to undertake base exchanges, remove parts of sequences or add natural or synthetic sequences. To connect the DNA fragments to each other, adapters or linkers may be added to the fragments.

[0289]

For example, the generation of plant cells with a reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect, or by expressing at least one suitably constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product.

[0290]

To this end, it is firstly possible to use DNA molecules which encompass the entire coding sequence of a gene product inclusive of any flanking sequences which may be present, and also DNA molecules which only encompass portions of the coding sequence, in which case it is necessary for these portions to be long enough to have an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical to them.

[0291]

When expressing nucleic acid molecules in plants, the protein synthesized may be localized in any desired compartment of the plant cell. However, to achieve localization in a particular compartment, it is possible, for example, to join the coding region to DNA sequences which ensure localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227). The nucleic acid molecules can also be expressed in the organelles of the plant cells.

[0292]

The transgenic plant cells can be regenerated by known techniques to give rise to entire plants. In principle, the transgenic plants may be plants of any desired plant species, i.e. not only monocotyledonous but also dicotyledonous plants.

[0293]

Thus, transgenic plants can be obtained whose properties are altered by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or expression of heterologous (=foreign) genes or gene sequences.

[0294]

It is preferred to employ the compounds (I) according to the invention in transgenic crops which are resistant to growth regulators such as, for example, dicamba, or against herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or against herbicides from the group of the sulfonylureas, glyphosate, glufosinate or benzoylisoxazoles and analogous active ingredients.

[0295]

When the active ingredients of the invention are used in transgenic crops, not only do the effects toward harmful plants which are observed in other crops occur, but often also effects which are specific to application in the particular transgenic crop, for example an altered or specifically widened spectrum of weeds which can be controlled, altered application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influencing of growth and yield of the transgenic crop plants.

[0296]

The invention therefore also relates to the use of the compounds of the formula (I) according to the invention and/or their salts as herbicides for controlling harmful plants in crops of useful plants or ornamentals, optionally in transgenic crop plants.

[0297]

Preference is given to the use in cereals, here preferably maize, wheat, barley, rye, oats, millet or rice, by the pre- or post-emergence method.

[0298]

Preference is also given to the use in soy beans by the pre- or post-emergence method.

[0299]

The use according to the invention for the control of harmful plants or for growth regulation of plants also includes the case in which the active ingredient of the formula (I) or its salt is not formed from a precursor substance (“prodrug”) until after application on the plant, in the plant or in the soil.

[0300]

The invention also provides the use of one or more compounds of the formula (I) or salts thereof or of a composition according to the invention (as defined below) (in a method) for controlling harmful plants or for regulating the growth of plants which comprises applying an effective amount of one or more compounds of the formula (I) or salts thereof onto the plants (harmful plants, if appropriate together with the useful plants), plant seeds, the soil in which or on which the plants grow or the area under cultivation.

[0301]

The invention also provides a herbicidal or plant growth-regulating composition, characterized in that the composition

[0000]

(a) comprises one or more compounds of the formula (I) and/or salts thereof as defined above, preferably one or more compounds of the formula (Ia) and/or salts thereof, in each case as defined above,
and
(b) one or more further substances selected from groups (i) and/or (ii):
(i) one or more further agrochemically active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides (i.e. those not corresponding to the formula (I) defined above), fungicides, safeners, fertilizers and/or further growth regulators,
(ii) one or more formulation auxiliaries customary in crop protection.

[0302]

A herbicidal or plant growth-regulating composition according to the invention comprises preferably one, two, three or more formulation auxiliaries (ii) customary in crop protection selected from the group consisting of surfactants, emulsifiers, dispersants, film-formers, thickeners, inorganic salts, dusting agents, carriers solid at 25° C. and 1013 mbar, preferably absorbent granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoam agents, water, organic solvents, preferably organic solvents miscible with water in any ratio at 25° C. and 1013 mbar.

[0303]

The compounds (I) according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting products or granules in the customary formulations. The invention therefore also provides herbicidal and plant growth-regulating compositions which comprise compounds of the formula (I) and/or salts thereof.

[0304]

The compounds of the formula (I) and/or salts thereof can be formulated in various ways according to which biological and/or physicochemical parameters are required. Possible formulations include, for example: Wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions, capsule suspensions (CS), dusting products (DP), dressings, granules for scattering and soil application, granules (GR) in the form of microgranules, spray granules, absorption and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

[0305]

These individual formulation types and the formulation assistants, such as inert materials, surfactants, solvents and further additives, are known to the person skilled in the art and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd ed., Darland Books, Caldwell N.J.; H. v. Olphen, “Introduction to Clay Colloid Chemistry”, 2nd ed., J. Wiley & Sons, N.Y.; C. Marsden, “Solvents Guide”, 2nd ed., Interscience, N.Y. 1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler, “Chemische Technologic” [Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th Ed. 1986.

[0306]

Wettable powders are preparations which can be dispersed uniformly in water and, in addition to the active ingredient, apart from a diluent or inert substance, also comprise surfactants of the ionic and/or nonionic type (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate. To produce the wettable powders, the herbicidally active ingredients are finely ground, for example in customary apparatuses such as hammer mills, blower mills and air jet mills, and simultaneously or subsequently mixed with the formulation auxiliaries.

[0307]

Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene, or else relatively high-boiling aromatics or hydrocarbons or mixtures of the organic solvents, with addition of one or more ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers which may be used are: calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.

[0308]

Dustable powders are obtained by grinding the active ingredient with finely distributed solid substances, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

[0309]

Suspension concentrates may be water- or oil-based. They may be prepared, for example, by wet-grinding by means of commercial bead mills and optional addition of surfactants as have, for example, already been listed above for the other formulation types.

[0310]

Emulsions, for example oil-in-water emulsions (EW), can be produced, for example, by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and optionally surfactants as already listed above, for example, for the other formulation types.

[0311]

Granules can be prepared either by spraying the active ingredient onto adsorptive granular inert material or by applying active ingredient concentrates to the surface of carriers, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules—if desired as a mixture with fertilizers.

[0312]

Water-dispersible granules are produced generally by the customary processes such as spray-drying, fluidized bed granulation, pan granulation, mixing with high-speed mixers and extrusion without solid inert material.

[0313]

For the production of pan, fluidized-bed, extruder and spray granules, see e.g. processes in “Spray Drying Handbook” 3rd Ed. 1979, G. Goodwin Ltd., London, J. E. Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff, “Perry's Chemical Engineer's Handbook”, 5th Ed., McGraw Hill, New York 1973, p. 8-57.

[0314]

For further details regarding the formulation of crop protection compositions, see, for example, G. C. Klingman, “Weed Control as a Science”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

[0315]

The agrochemical preparations, preferably herbicidal or plant growth-regulating compositions, of the present invention preferably comprise a total amount of from 0.1 to 99% by weight, preferably 0.5 to 95% by weight, particularly preferably 1 to 90% by weight, especially preferably 2 to 80% by weight, of active ingredients of the formula (I) and their salts.

[0316]

In wettable powders, the active ingredient concentration is, for example, about 10% to 90% by weight, the remainder to 100% by weight consisting of customary formulation constituents. In emulsifiable concentrates, the active ingredient concentration may be about 1% to 90% and preferably 5% to 80% by weight. Formulations in the form of dusts comprise 1% to 30% by weight of active ingredient, preferably usually 5% to 20% by weight of active ingredient; sprayable solutions contain about 0.05% to 80% by weight, preferably 2% to 50% by weight of active ingredient. In the case of water-dispersible granules, the active ingredient content depends partially on whether the active compound is present in liquid or solid form and on which granulation auxiliaries, fillers, etc., are used. In the water-dispersible granules, the content of active ingredient is, for example, between 1% and 95% by weight, preferably between 10% and 80% by weight.

[0317]

In addition, the active ingredient formulations mentioned optionally comprise the respective customary stickers, wetters, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents which influence the pH and the viscosity. Examples of formulation auxiliaries are described inter alia in “Chemistry and Technology of Agrochemical Formulations”, ed. D. A. Knowles, Kluwer Academic Publishers (1998).

[0318]

The compounds of the formula (I) or salts thereof can be employed as such or in the form of their preparations (formulations) combined with other pesticidally active compounds, such as, for example, insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and/or growth regulators, for example as finished formulation or as tank mixes. The combination formulations can be prepared on the basis of the abovementioned formulations, while taking account of the physical properties and stabilities of the active ingredients to be combined.

[0319]

Active ingredients which can be employed in combination with the compounds of formula (I) according to the invention in mixture formulations or in a tank mix are, for example, known active ingredients based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoendesaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and literature cited therein.

[0320]

Of particular interest is the selective control of harmful plants in crops of useful plants and ornamentals. Although the compounds (I) according to the invention have already demonstrated very good to adequate selectivity in a large number of crops, in principle, in some crops and in particular also in the case of mixtures with other, less selective herbicides, phytotoxicities on the crop plants may occur. In this connection, combinations of compounds (I) according to the invention are of particular interest which comprise the compounds (I) or their combinations with other herbicides or pesticides and safeners. The safeners, which are used in an antidotically effective amount, reduce the phytotoxic side effects of the herbicides/pesticides employed, for example in economically important crops, such as cereals (wheat, barley, rye, corn, rice, millet), sugarbeet, sugarcane, oilseed rape, cotton and soybeans, preferably cereals.

[0321]

The weight ratios of herbicide (mixture) to safener depend generally on the herbicide application rate and the efficacy of the safener in question and may vary within wide limits, for example in the range from 200:1 to 1:200, preferably 100:1 to 1:100, in particular 20:1 to 1:20. Analogously to the compounds (I) or mixtures thereof, the safeners can be formulated with further herbicides/pesticides and be provided and employed as a finished formulation or tank mix with the herbicides.

[0322]

For application, the herbicide or herbicide/safener formulations present in commercial form are, if appropriate, diluted in a customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules with water. Dust-type preparations, granules for soil application or granules for scattering and sprayable solutions are not normally diluted further with other inert substances prior to application.

[0323]

The application rate of the compounds of the formula (I) and/or their salts is affected to a certain extent by external conditions such as temperature, humidity, etc. Here, the application rate may vary within wide limits. For the application as a herbicide for controlling harmful plants, the total amount of compounds of the formula (I) and their salts is preferably in the range from 0.001 to 10.0 kg/ha, with preference in the range from 0.005 to 5 kg/ha, more preferably in the range from 0.01 to 1.5 kg/ha, in particular in the range from 0.05 to 1 kg/ha. This applies both to application by the pre-emergence method and the post-emergence method, the pre-emergence treatment being preferred by virtue of the significantly higher activity.

[0324]

When the compounds of the formula (I) and/or their salts are used as plant growth regulator, for example as culm stabilizer for crop plants like those mentioned above, preferably cereal plants, such as wheat, barley, rye, triticale, millet, rice or maize, the total application rate is preferably in the range of from 0.001 to 2 kg/ha, preferably in the range of from 0.005 to 1 kg/ha, in particular in the range of from 10 to 500 g/ha, very particularly in the range from 20 to 250 g/ha. This applies both to the pre-emergence and the post-emergence application.

[0325]

The application as culm stabilizer may take place at various stages of the growth of the plants. Preferred is, for example, the application after the tillering phase, at the beginning of the longitudinal growth.

[0326]

As an alternative, application as plant growth regulator is also possible by treating the seed, which includes various techniques for dressing and coating seed. Here, the application rate depends on the particular techniques and can be determined in preliminary tests.

[0327]

The symbols “>” and “<” mean “greater than” and “smaller than”, respectively. The symbol “≧” means “greater than or equal to”, the symbol “≦” means “smaller than or equal to”.

[0328]

If, in the context of the description and the examples, the designations “R” and “S” are stated for the absolute configuration at a center of chirality of the stereoisomers of the formulae (I) and (Ia), this follows the RS nomenclature of the Cahn-Ingold-Prelog rules.

ABBREVIATIONS AND DESIGNATIONS USED

[0000]

  • Ex.=Example number
  • H=hydrogen (atom)
  • Me=methyl
  • Et=ethyl
  • n-Pr=n-propyl
  • i-Pr=isopropyl
  • n-Bu=n-butyl
  • i-Bu=isobutyl
  • F, Cl, Br, I=fluorine, chlorine, bromine and iodine, respectively, in accordance with the conventional chemical atom symbols
  • MeO or OMe=methoxy
  • CN=cyano
  • NO2=nitro

[0341]

The position of a substituent at a (phenyl) ring, for example in position 2 or position 3, is stated as a prefix to the symbol or the abbreviation of the radical, for example

[0000]

2-Cl=2-chloro
2-Me=2-methyl
3-NO2=3-nitro

[0342]

Numerations of the substituent positions for di- or trisubstituted substitution patterns are analogously stated as a prefix, for example

[0000]

3,5-Me2=3,5-dimethyl (e.g. as substitution at the phenyl ring)
2,3,6-F3or 2,3,6-F3=2,3,6-trifluoro (e.g. as substitution at the phenyl ring)
2,3-F2or 2,3-F2=2,3-difluoro (e.g. as substitution at the phenyl ring)

[0343]

Other abbreviations are to be understood analogously to the examples stated above.

[0000]

“(R2)n═“H”=unsubstituted heteroaromatic radical Q (n=0)
“(R3)m═“H”=unsubstituted phenyl ring (m=0)

[0344]

In addition, the customary chemical symbols and formulae apply, such as, for example, CH2for methylene or CF3for trifluoromethyl or OH for hydroxyl. Correspondingly, composite meanings are defined as composed of the abbreviations mentioned.

[0345]

In an exemplary manner, some synthesis examples of compounds of the formula (I) are described below.

[0346]

In the examples, the amounts (including the percentages) refer to the weight, unless stated otherwise.

SYNTHESIS EXAMPLES

1a) Preparation of methyl 4-(5-chloro-6-fluoropyridin-3-yl)-4-cyano-3-(2,5-difluorophenyl)butanoate

[0347]

Under protective gas (argon), 293 mg (2.612 mmol) of potassium tert-butoxide were added to 2.228 g (13.061 mmol) of methyl 3-(2,6-difluorophenyl)acrylate and 2.381 g (12.016 mmol) of (5-chloro-6-fluoropyridin-3-yl)acetonitrile in 20.0 ml of toluene and 2 ml of DMF, and the mixture was stirred at 60° C. for 20 h. After removal of the solvent under reduced pressure, the residue was taken up in ethyl acetate and washed twice with in each case 50 ml of water. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. Chromatography of the residue over silica gel (ethyl acetate/heptane=15:85) gave 2.900 g (61% of theory) of the diastereomeric methyl 4-(5-chloro-6-fluoropyridin-3-yl)-4-cyano-3-(2,5-difluorophenyl)butanoates (erythro:threo=55:45, comparison of the doublet in1H-NMR in CDCl3at 4.58 and 4.21 ppm).

1b) Preparation of 2-(5-chloro-6-fluoropyridin-3-yl)-3-(2,5-difluorophenyl)-5-hydroxypentanenitrile

[0348]

Under protective gas (Ar), 2.9 g (7.87 mmol) of methyl 4-(5-chloro-6-fluoropyridin-3-yl)-4-cyano-3-(2,5-difluorophenyl)butanoate from synthesis example 1a) in 10 ml of THF were added to 0.848 g (15.73 mmol) of potassium borohydride and 0.333 g (7.87 mmol) of lithium chloride in 5 ml of THF, and the mixture was stirred at 70° C. for 5 h. After cooling to 0° C., water was added. The residue was then taken up in ethyl acetate and washed twice with in each case 50 ml of water. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. Chromatography of the residue over silica gel (ethyl acetate/heptane=15:85) gave 1.700 g (64% of theory) of the diastereomeric 2-(5-chloro-6-fluoropyridin-3-yl)-3-(2,5-difluorophenyl)-5-hydroxypentanenitriles (erythro:threo=57:43, comparison of the doublet in1H-NMR in CDCl3at 4.38 and 4.15 ppm).

1c) Preparation of (2R,3R)-2-(5-chloro-6-fluoropyridin-3-yl)-3-(2,5-difluorophenyl)-5-hydroxypentanenitrile

[0349]

Preparative chromatography [(80 ml/min n-heptane/2-propanol (80:20)] of 100 mg of the diastereomer mixture obtained according to synthesis example 1b) above (dissolved in 4.0 ml of methanol) on a chiral solid phase column [Chiralpak IC, 20 μm, (250×50) mm column] gave 7 mg of (2R,3R)-2-(5-chloro-6-fluoropyridin-3-yl)-3-(2,5-difluorophenyl)-5-hydroxypentanenitrile which eluted as the last of the four stereoisomers (retention time: 13.0 min). The absolute configuration was then assigned by X-ray structural analysis.

2a) Preparation of methyl 4-cyano-3-(2,6-difluorophenyl)-4-(3-thienyl)butanoate

[0350]

Under protective gas (Ar), 182 mg (1.624 mmol) of potassium tert-butoxide were added to 1.609 g (8.118 mmol) of methyl 3-(2,6-difluorophenyl)acrylate and 1.000 g (8.118 mmol) of 3-thienylacetonitrile in 45.0 ml of toluene and 2 ml of DMF, and the mixture was stirred at 60° C. for 6 h. After removal of the solvent under reduced pressure, the residue was taken up in ethyl acetate and washed twice with in each case 50 ml of water. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. Chromatography of the residue over silica gel (ethyl acetate/heptane=15:85) gave 1.750 g (68% of theory) of the diastereomeric methyl 4-cyano-3-(2,6-difluorophenyl)-4-(3-thienyl)butanoates (erythro:threo=24:76, comparison of the doublet in1H-NMR in CDCl3at 4.33 and 4.16 ppm).

2b) Preparation of 3-(2,6-difluorophenyl)-5-hydroxy-2-(3-thienyl)pentanenitrile

[0351]

Under protective gas (Ar), 0.100 g (0.311 mmol) of methyl 4-cyano-3-(2,6-difluorophenyl)-4-(3-thienyl)butanoate in 2 ml THF were added to 0.017 g (0.311 mmol) of potassium borohydride and 0.013 g (0.311 mmol) of lithium chloride in 1 ml of THF, and the mixture was stirred at 70° C. for 5 h. After cooling to 0° C., water was added. The residue was then taken up in ethyl acetate and washed twice with in each case 50 ml of water. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. Chromatography of the residue over silica gel (ethyl acetate/heptane=15:85) gave 0.044 g (45% of theory) of the diastereomeric 3-(2,6-difluorophenyl)-5-hydroxy-2-(3-thienyl)pentanenitriles (erythro:threo=59:41, comparison of the doublet in1H-NMR in CDCl3at 6.92 and 6.76 ppm).

[0352]

Definition and Description of Preferred Compounds According to the Invention—Analytical and Physical Data

[0353]

Information regarding the examples given in Tables 4a to 4d:

[0354]

In Tables 4a to 4d below, the compounds according to the invention are assigned corresponding individual numbers (=example numbers), where the particular example number is composed of the compound number of the chemical formula (I), which refers to the same number as given in the respective line of Tables 1 to 3, followed by the respective stereoisomeric form. The particular stereoisomeric form corresponds to the above-defined formulae (I threo-1), (I threo-2), (I erythro-1) and (I erythro-2), or mixtures of these stereoisomers.

[0355]

The same applies to the assignment of racemic or optically active threo stereoisomers or erythro stereoisomers of the compounds according to the invention.

[0356]

In this way, the stereoisomers are given the respective clearly defined chemical structure of a compound of the formula (I) according to the invention, which the following examples aim to illustrate:

[0357]

The compound name “1 threo-2” identifies the “threo-2” isomers of the compound of the formula (I) [corresponding to formula I (I threo-2)], in which R1═H (=hydrogen), and Q(R2)n=6-fluoropyridin-3-yl and (R3)m, =2,6-F2according to entry number 1 from Table 1.

[0358]

The compound name “14 erythro-1” identifies the “erythro-1” isomers of the compound of the formula (I) [corresponding to formula I (I erythro-1)], in which R1═H (=hydrogen), and Q(R2)n=5-chloro-6-fluoropyridin-3-yl and (R3)m=2,6-F2according to entry number 14 from Table 1.

[0359]

The compound name “85 erythro” identifies a mixture of the “erythro” isomers of the compound of the formula (I) in which R1═H (=hydrogen), and Q(R2)n=pyridin-3-yl and (R3)m=2,6-F2according to entry number 85 from Table 1.

[0360]

The compound name “460 threo-2” identifies the “threo-2” isomers of the compound of the formula (I) [corresponding to formula (I threo-2)], in which R1═H (=hydrogen), and Q(R2)n=6-chloropyridin-3-yl and (R3)m=2,5-F2according to entry number 460 from Table 1.

[0361]

The compound name “472 erythro-2” identifies the “erythro-2” isomers of the compound of the formula (I) [corresponding to formula (I erythro-2)], in which R1═H (=hydrogen), and Q(R2)n=5-chloro-6-fluoropyridin-3-yl and (R3)m=2,5-F2according to entry number 472 from Table 1.

[0362]

Tables 4a to 4d: Preferred compounds of the formulae (I threo-1), (I threo-2), (I erytro-1) and (I erytro-2) according to the invention

[0000]

(I threo) = (I threo-1) + (I threo-2) (50:50) = (rac.)

[0363]

Table 4a describes the compounds of the formulae (1 threo-1) to (3981 threo-1), in which the structure combination of the groups R′, Q(R2)nand (R3)mis defined according to a line number from Tables 1 to 3, as explained in detail above.

[0364]

Table 4b: Preferred (I Threo-2) Enantiomers

[0365]

Table 4b describes the compounds of the formulae (1 threo-2) to (3981 threo-2), in which the structure combination of the groups R′, Q(R2)nand (R3)mis defined according to a line number from Tables 1 to 3, as explained in detail above.

[0000]

(I erythro) = (I erythro-1) + (I erythro-2) (50:50) = (rac.)

[0366]

Table 4c describes the compounds of the formulae (1 erythro-1) to (3981 erythro-1), in which the structure combination of the groups R′, Q(R2)nand (R3)mis defined according to a line number from Tables 1 to 3, as explained in detail above.

[0367]

Table 4d: Preferred (I erythro-2) Enantiomers

[0368]

Table 4d describes the compounds of the formulae (1 erythro-2) to (3981 erythro-2), in which the structure combination of the groups R′, Q(R2)nand (R3)mis defined according to a line number from Tables 1 to 3, as explained in detail above.

[0369]

Physical Data of Some Compounds According to the Invention:

[0370]

Test Methods:

  • 1) NMR=1H-NMR data (400 MHz, CDCl3); characteristic chemical shifts [in ppm] are given for the respective example.
  • 2) HPLC=High Performance Liquid Chromatography, column: Zorbax Eclipse, 50×3.0, C18 1.8 μm, mobile phase: water+0.06% formic acid/acrylonitrile+0.06% formic acid, gradient: 90:10, after 2 min 5:95; detector: DAD (210-400 nm); retention time (Rt) indicated for the example in question,
  • 3) chiral HPLC=HPLC on a chiral column, column: Chiralpak IC, 250×4.6 mm, 5 μm DAIC 83325, detector wavelength: 210 nm; column temperature 25° C.,
    • mobile phase a: (n-heptane:2-propanol), (60:40), Chromasolv, flow rate: 1.0 ml/min
    • mobile phase b: (n-heptane:2-propanol), (70:30), Chromasolv, flow rate: 1.0 ml/min
    • mobile phase c: (n-heptane:2-propanol), (80:20), Chromasolv, flow rate: 1.0 ml/min
    • mobile phase d: (n-heptane:2-propanol), (90:10), Chromasolv, flow rate: 0.6 ml/min

[0378]

NMR Data of Selected Examples

[0379]

1H-NMR data (CDCl3)—chemical shift of selected characteristic signals in ppm.

[0380]

NMR Peak List Method

[0381]

The 1H-NMR data of selected examples are noted in the form of 1H-NMR peak lists. For each signal peak, first the δ value in ppm and then the signal intensity in round brackets are listed. The pairs of δ value-signal intensity numbers for different signal peaks are listed with separation from one another by semicolons.

[0382]

The peak list for one example therefore has the form:

[0000]

δ1(intensity1); δ2(intensity2); . . . ; δi(intensityi); . . . ; δn(intensityn)

[0383]

The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. In the case of broad signals, several peaks or the middle of the signal and the relative intensity thereof may be shown in comparison to the most intense signal in the spectrum.

[0384]

Calibration of the chemical shift of 1H NMR spectra is accomplished using tetramethylsilane and/or the chemical shift of the solvent, particularly in the case of spectra which are measured in DMSO. Therefore, the tetramethylsilane peak may but need not occur in NMR peak lists.

[0385]

The lists of the 1H-NMR peaks are similar to the classic 1H-NMR prints and thus usually comprise all peaks listed in classic NMR interpretations.

[0386]

In addition, like classic 1H-NMR prints, they may show solvent signals, signals of stereoisomers of the target compounds, which are likewise part of the subject matter of the invention, and/or peaks of impurities.

[0387]

When stating compound signals in the delta range of solvents and/or water, in our lists of 1H NMR peaks, the usual solvent peaks, for example peaks of DMSO in DMSO-D6and the peak of water are shown, which usually have on average a high intensity.

[0388]

The peaks of stereoisomers of the target compounds and/or peaks of impurities usually have a lower intensity on average than the peaks of the target compounds (for example with a purity of >90%).

[0389]

Such stereoisomers and/or impurities may be typical of the particular preparation process. Their peaks can thus help in identifying reproduction of our preparation process with reference to “by-product fingerprints”.

[0390]

An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can, if required, isolate the peaks of the target compounds, optionally using additional intensity filters. This isolation would be similar to the relevant peak picking in classical 1H-NMR interpretation.

[0391]

Further details of 1H NMR peak lists can be found in the Research Disclosure Database Number 564025.

[0392]

Example 186:1H-NMR (400.0 MHz, CDCl3): δ=7.519 (1.1); 7.397 (5.8); 7.390 (6.9); 7.385 (6.4); 7.377 (7.5); 7.314 (6.6); 7.313 (6.6); 7.310 (7.2); 7.309 (7.0); 7.306 (5.6); 7.305 (5.7); 7.303 (5.8); 7.302 (5.7); 7.299 (3.9); 7.294 (2.4); 7.283 (2.3); 7.278 (7.4); 7.273 (2.9); 7.2703 (1.4); 7.2695 (1.4); 7.269 (1.5); 7.268 (1.7); 7.267 (2.0); 7.266 (2.3); 7.265 (2.7); 7.260 (182.9); 7.254 (1.6); 7.253 (1.0); 7.2524 (0.7); 7.2516 (0.6); 7.241 (1.9); 7.226 (0.7); 7.187 (6.4); 7.180 (7.4); 7.175 (7.1); 7.171 (2.5); 7.168 (8.1); 7.155 (4.0); 7.148 (8.5); 7.145 (7.6); 7.139 (2.6); 7.134 (10.2); 7.132 (8.2); 7.129 (2.8); 7.118 (3.0); 7.113 (4.3); 7.097 (2.1); 7.055 (5.9); 7.051 (6.5); 7.047 (5.6); 7.044 (5.5); 6.996 (1.1); 6.962 (3.3); 6.958 (7.3); 6.941 (3.4); 6.936 (11.6); 6.931 (3.7); 6.920 (7.1); 6.916 (9.8); 6.910 (3.7); 6.907 (6.4); 6.904 (6.0); 6.788 (3.0); 6.784 (7.6); 6.762 (12.2); 6.741 (6.5); 5.298 (2.6); 4.407 (7.5); 4.380 (16.0); 4.352 (9.3); 3.908 (1.6); 3.898 (1.6); 3.880 (2.8); 3.870 (2.8); 3.852 (2.8); 3.841 (2.7); 3.824 (2.6); 3.813 (2.6); 3.797 (1.4); 3.787 (1.3); 3.705 (1.5); 3.693 (1.8); 3.689 (1.8); 3.677 (3.3); 3.666 (2.3); 3.662 (2.3); 3.650 (1.9); 3.552 (1.3); 3.541 (1.6); 3.536 (1.6); 3.525 (3.1); 3.514 (2.1); 3.509 (2.2); 3.497 (2.7); 3.482 (1.8); 3.473 (2.0); 3.460 (2.0); 3.446 (1.4); 3.432 (1.3); 3.388 (1.5); 3.375 (1.7); 3.366 (1.9); 3.352 (1.8); 3.340 (1.3); 3.326 (1.1); 2.512 (1.0); 2.502 (1.1); 2.496 (1.1); 2.489 (1.2); 2.486 (1.3); 2.478 (1.9); 2.467 (1.6); 2.462 (1.9); 2.455 (1.7); 2.452 (1.7); 2.445 (1.5); 2.439 (1.4); 2.429 (1.3); 2.302 (0.5); 2.299 (1.0); 2.295 (0.6); 2.288 (1.4); 2.285 (1.4); 2.278 (0.7); 2.274 (1.3); 2.270 (1.4); 2.257 (1.8); 2.253 (1.6); 2.246 (1.2); 2.240 (1.1); 2.236 (1.0); 2.224 (0.9); 2.222 (0.9); 2.211 (0.6); 2.045 (0.6); 2.033 (0.8); 2.031 (0.9); 2.020 (0.8); 2.014 (0.9); 2.010 (1.2); 2.006 (1.3); 2.003 (1.4); 1.999 (1.6); 1.996 (1.5); 1.993 (1.1); 1.985 (1.3); 1.983 (1.3); 1.971 (1.3); 1.969 (1.3); 1.961 (0.6); 1.958 (0.8); 1.894 (1.2); 1.883 (1.3); 1.878 (1.4); 1.872 (1.4); 1.867 (1.5); 1.861 (1.9); 1.857 (1.4); 1.845 (1.9); 1.838 (1.0); 1.833 (0.9); 1.827 (0.9); 1.822 (0.8); 1.811 (0.7); 1.556 (0.7); 1.284 (1.1); 1.255 (1.1); 1.216 (1.0); 1.201 (1.0); 0.008 (1.9); 0.000 (64.4); −0.006 (0.6); −0.009 (1.8)

[0393]

Example 86:1H-NMR (400.0 MHz, CDCl3): δ=8.667 (5.4); 8.665 (5.8); 8.663 (6.2); 8.660 (5.6); 8.655 (5.7); 8.653 (6.2); 8.650 (6.1); 8.648 (5.5); 8.486 (5.5); 8.483 (5.9); 8.481 (5.9); 8.479 (5.6); 8.474 (5.5); 8.471 (6.1); 8.469 (5.9); 8.467 (5.4); 7.764 (5.0); 7.760 (5.1); 7.745 (10.3); 7.740 (10.1); 7.726 (6.4); 7.721 (6.2); 7.558 (5.2); 7.553 (5.1); 7.539 (9.8); 7.534 (9.9); 7.519 (10.3); 7.515 (6.2); 7.430 (6.4); 7.428 (11.9); 7.425 (6.9); 7.411 (5.9); 7.408 (10.7); 7.406 (6.2); 7.321 (6.8); 7.318 (6.7); 7.314 (2.8); 7.309 (7.0); 7.306 (6.9); 7.302 (6.7); 7.299 (8.0); 7.293 (4.4); 7.290 (6.9); 7.287 (6.5); 7.282 (4.0); 7.277 (11.6); 7.272 (6.4); 7.271 (6.0); 7.260 (1049.0); 7.248 (1.8); 7.240 (3.1); 7.160 (9.0); 7.140 (14.7); 7.138 (11.7); 7.128 (7.0); 7.126 (6.2); 7.121 (10.3); 7.119 (6.2); 7.116 (4.2); 7.109 (6.4); 7.107 (5.9); 7.100 (9.7); 7.095 (3.0); 7.084 (3.6); 7.079 (5.2); 7.063 (2.6); 6.996 (6.0); 6.961 (4.4); 6.956 (9.7); 6.939 (4.6); 6.935 (16.0); 6.930 (4.9); 6.913 (8.4); 6.909 (4.1); 6.748 (9.5); 6.726 (15.8); 6.705 (8.2); 4.527 (11.0); 4.502 (12.6); 4.450 (12.9); 4.423 (15.2); 4.140 (2.0); 4.129 (3.6); 4.114 (4.2); 102 (6.9); 4.090 (4.0); 4.075 (3.4); 4.064 (1.9); 3.726 (1.0); 3.714 (2.1); 3.698 (3.3); 3.686 (3.8); 3.671 (2.7); 3.658 (1.4); 3.549 (1.9); 3.535 (3.8); 3.522 (5.2); 3.510 (5.5); 3.498 (4.3); 3.485 (2.4); 3.471 (1.1); 3.428 (1.3); 3.414 (2.6); 3.400 (2.6); 3.394 (2.8); 3.379 (2.4); 3.366 (1.8); 3.352 (0.9); 2.555 (1.3); 2.544 (1.4); 2.539 (1.2); 2.533 (1.4); 2.528 (1.5); 2.521 (2.4); 2.505 (2.3); 2.499 (2.0); 2.494 (1.9); 2.488 (1.9); 2.483 (1.7); 2.472 (1.5); 2.344 (1.3); 2.331 (1.7); 2.316 (1.7); 2.303 (2.0); 2.269 (1.3); 2.257 (0.8); 2.108 (1.1); 2.095 (1.4); 2.081 (1.9); 2.059 (2.2); 2.047 (2.1); 2.034 (1.8); 2.020 (1.0); 1.830 (1.5); 1.814 (1.9); 1.809 (1.8); 1.803 (1.8); 1.797 (2.4); 1.781 (2.4); 1.768 (1.4); 1.763 (1.3); 1.747 (1.1); 1.548 (123.1); 1.440 (3.8); 1.426 (7.2); 1.408 (7.8); 1.394 (3.6); 0.146 (1.2); 0.069 (1.5); 0.008 (12.7); 0.007 (4.5); 0.006 (4.7); 0.000 (409.7); −0.007 (2.9); −0.009 (10.9); −0.150 (1.2)

[0394]

Example 544:1H-NMR (400.0 MHz, CDCl3): δ=8.606 (6.1); 8.603 (6.9); 8.601 (7.2); 8.599 (6.7); 8.594 (6.9); 8.589 (10.5); 8.587 (10.3); 8.583 (6.0); 8.578 (5.4); 8.576 (6.0); 8.574 (5.9); 8.571 (5.4); 7.662 (5.8); 7.658 (6.1); 7.656 (5.5); 7.651 (5.3); 7.643 (11.6); 7.639 (12.3); 7.636 (10.9); 7.632 (9.7); 7.624 (7.2); 7.619 (7.2); 7.617 (6.6); 7.612 (5.9); 7.519 (2.8); 7.311 (0.6); 7.294 (0.7); 7.292 (0.5); 7.269 (10.2); 7.266 (17.4); 7.260 (483.9); 7.254 (10.4); 7.250 (7.8); 7.247 (11.3); 7.245 (9.9); 7.238 (6.6); 7.235 (8.1); 7.231 (5.4); 7.221 (5.6); 7.219 (5.3); 7.215 (5.6); 7.212 (5.1); 7.207 (7.4); 7.205 (12.6); 7.203 (11.7); 7.200 (5.5); 7.188 (6.6); 7.185 (11.3); 7.183 (7.0); 7.173 (3.8); 7.167 (3.8); 7.159 (6.2); 7.151 (3.3); 7.144 (3.7); 7.137 (3.5); 7.000 (2.0); 6.996 (3.1); 6.988 (2.7); 6.976 (5.1); 6.964 (5.1); 6.960 (2.2); 6.956 (1.5); 6.952 (5.2); 6.945 (3.5); 6.940 (7.7); 6.933 (6.1); 6.930 (5.1); 6.923 (12.6); 6.916 (6.3); 6.913 (10.9); 6.911 (11.6); 6.902 (12.8); 6.894 (7.4); 6.890 (8.4); 6.885 (10.0); 6.878 (6.1); 6.877 (6.0); 6.871 (3.1); 6.866 (7.6); 4.487 (15.1); 4.468 (16.0); 4.337 (12.5); 4.319 (13.9); 3.997 (2.0); 3.986 (2.2); 3.978 (2.0); 3.969 (3.4); 3.957 (3.8); 3.939 (5.2); 3.920 (3.8); 3.900 (2.0); 3.667 (3.4); 3.654 (4.7); 3.640 (5.7); 3.627 (4.0); 3.547 (1.6); 3.530 (2.8); 3.516 (2.4); 3.485 (1.8); 3.461 (2.0); 2.313 (1.1); 2.301 (1.3); 2.297 (1.2); 2.291 (1.1); 2.286 (1.4); 2.278 (2.8); 2.262 (2.7); 2.256 (2.5); 2.251 (2.4); 2.245 (2.4); 2.241 (2.3); 2.229 (1.9); 2.213 (1.4); 2.210 (1.4); 2.199 (2.8); 2.185 (2.6); 2.172 (2.7); 2.161 (2.1); 2.150 (1.3); 2.137 (1.4); 2.123 (0.7); 2.116 (0.6); 2.102 (1.2); 2.080 (3.1); 2.066 (5.0); 2.060 (4.7); 2.053 (2.8); 2.046 (9.6); 2.031 (5.4); 2.027 (6.2); 2.012 (3.5); 1.992 (1.3); 1.977 (0.6); 1.664 (2.6); 1.586 (30.1); 0.146 (0.5); 0.008 (5.6); 0.000 (194.5); −0.009 (5.5); −0.150 (0.6)

[0395]

Example 472:1H-NMR (400.0 MHz, CDCl3): δ=7.902 (11.4); 7.897 (12.9); 7.893 (11.5); 7.860 (8.0); 7.855 (9.9); 7.851 (9.2); 7.791 (9.4); 7.785 (7.9); 7.771 (9.3); 7.765 (8.0); 7.581 (10.3); 7.575 (10.4); 7.560 (10.4); 7.554 (9.9); 7.519 (9.9); 7.310 (1.1); 7.295 (1.4); 7.292 (2.6); 7.287 (2.3); 7.260 (1776.8); 7.227 (1.6); 7.210 (1.4); 7.188 (4.9); 7.181 (5.6); 7.174 (5.3); 7.167 (9.6); 7.159 (5.1); 7.153 (4.7); 7.145 (5.1); 7.034 (2.5); 7.026 (3.3); 7.023 (3.4); 7.018 (3.1); 7.015 (4.2); 7.011 (7.7); 7.007 (5.9); 7.003 (6.9); 7.000 (10.3); 6.996 (15.7); 6.993 (6.7); 6.989 (7.9); 6.985 (11.3); 6.977 (11.9); 6.972 (6.1); 6.967 (6.5); 6.964 (9.3); 6.960 (9.8); 6.957 (5.2); 6.954 (5.7); 6.949 (9.5); 6.946 (6.0); 6.942 (3.9); 6.938 (10.9); 6.926 (11.1); 6.915 (4.0); 6.903 (3.6); 6.870 (3.7); 6.863 (3.3); 6.856 (3.6); 6.849 (6.5); 6.841 (3.5); 6.835 (3.8); 6.828 (2.9); 4.387 (15.1); 4.370 (16.0); 4.156 (10.9); 4.134 (11.7); 4.012 (3.1); 3.983 (2.9); 3.749 (4.9); 3.732 (6.7); 3.710 (7.3); 3.695 (4.5); 3.651 (2.3); 3.642 (2.4); 3.622 (4.0); 3.601 (2.5); 3.592 (2.8); 3.555 (3.4); 3.435 (1.9); 3.422 (2.5); 3.410 (2.9); 2.370 (1.6); 2.361 (1.9); 2.356 (1.9); 2.347 (3.2); 2.336 (3.0); 2.326 (2.8); 2.321 (3.2); 2.312 (4.8); 2.302 (2.6); 2.297 (2.2); 2.288 (2.1); 2.189 (1.5); 2.179 (2.8); 2.160 (2.9); 2.139 (5.5); 2.126 (6.8); 2.119 (7.7); 2.111 (4.9); 2.105 (11.0); 2.092 (5.9); 2.083 (6.2); 2.070 (3.8); 2.059 (1.4); 2.048 (1.6); 2.035 (1.0); 1.541 (201.2); 1.378 (5.3); 1.285 (4.0); 0.146 (1.7); 0.008 (18.2); 0.000 (636.7); −0.009 (17.1); −0.149 (1.7)

[0396]

Example 2043:1H-NMR (400.0 MHz, CDCl3): δ=8.647 (7.4); 8.644 (7.7); 8.635 (8.0); 8.631 (7.8); 8.600 (8.4); 8.596 (8.6); 8.484 (8.5); 8.480 (8.8); 8.472 (9.1); 8.468 (8.8); 8.305 (8.6); 8.299 (8.7); 7.783 (3.4); 7.778 (4.2); 7.777 (4.2); 7.773 (3.5); 7.763 (4.0); 7.759 (4.7); 7.757 (4.8); 7.753 (3.8); 7.679 (3.6); 7.674 (4.7); 7.669 (3.6); 7.659 (4.2); 7.654 (5.2); 7.649 (3.9); 7.521 (1.0); 7.397 (4.7); 7.395 (4.7); 7.385 (4.9); 7.383 (4.8); 7.377 (4.6); 7.375 (4.4); 7.365 (4.5); 7.363 (4.3); 7.262 (164.2); 7.258 (9.2); 7.256 (8.0); 7.246 (6.6); 7.244 (6.4); 7.238 (6.0); 7.236 (5.8); 7.226 (5.5); 7.224 (5.3); 7.183 (2.3); 7.170 (2.3); 7.160 (4.5); 7.147 (4.5); 7.138 (4.6); 7.125 (4.5); 7.115 (2.2); 7.102 (2.0); 7.010 (1.8); 6.998 (2.2); 6.987 (4.5); 6.975 (4.6); 6.965 (4.7); 6.952 (4.7); 6.942 (2.3); 6.929 (3.1); 6.925 (2.3); 6.921 (2.2); 6.915 (2.1); 6.907 (3.3); 6.901 (3.5); 6.897 (3.4); 6.892 (3.3); 6.883 (1.9); 6.878 (1.9); 6.874 (1.8); 6.868 (1.7); 6.741 (1.6); 6.735 (1.9); 6.731 (1.8); 6.726 (1.8); 6.717 (2.9); 6.712 (3.2); 6.708 (3.2); 6.702 (2.9); 6.694 (1.7); 6.688 (1.7); 6.684 (1.6); 6.679 (1.5); 5.299 (16.0); 4.326 (8.6); 4.301 (9.7); 4.253 (9.4); 4.225 (11.4); 4.129 (0.5); 4.111 (0.5); 3.963 (1.9); 3.953 (2.0); 3.934 (3.6); 3.925 (3.7); 3.906 (1.9); 3.896 (2.0); 3.887 (2.0); 3.876 (2.0); 3.860 (3.3); 3.849 (3.3); 3.834 (1.9); 3.822 (1.8); 3.745 (2.3); 3.735 (2.5); 3.586 (2.0); 3.576 (2.2); 3.486 (1.7); 3.474 (2.1); 3.462 (2.5); 3.449 (2.0); 3.436 (1.6); 3.395 (1.6); 3.383 (2.0); 3.372 (2.3); 3.346 (1.4); 2.588 (1.2); 2.578 (1.3); 2.573 (1.4); 2.564 (2.1); 2.554 (2.6); 2.540 (2.5); 2.530 (2.9); 2.520 (1.9); 2.516 (1.8); 2.506 (1.6); 2.341 (1.1); 2.330 (1.9); 2.318 (1.5); 2.313 (1.5); 2.301 (2.4); 2.295 (2.2); 2.290 (1.8); 2.283 (1.4); 2.267 (1.6); 2.255 (0.9); 2.096 (0.7); 2.084 (1.3); 2.072 (1.1); 2.068 (1.2); 2.061 (1.8); 2.057 (1.9); 2.053 (1.9); 2.049 (2.3); 2.045 (1.9); 2.042 (2.6); 2.037 (1.6); 2.034 (1.6); 2.022 (1.9); 2.010 (1.0); 1.875 (1.2); 1.862 (1.7); 1.851 (1.8); 1.841 (2.6); 1.827 (2.5); 1.817 (1.5); 1.806 (1.4); 1.792 (1.0); 1.620 (7.1); 1.528 (3.2); 1.429 (2.9); 1.276 (0.6); 1.258 (1.2); 1.240 (0.7); 0.070 (0.6); 0.008 (2.3); 0.000 (68.2); −0.009 (2.4)

[0397]

Example 1:1H-NMR (400.0 MHz, CDCl3): δ=8.191 (7.6); 8.185 (7.9); 7.892 (8.9); 7.885 (9.5); 7.875 (4.2); 7.869 (3.9); 7.857 (4.2); 7.854 (4.6); 7.851 (4.3); 7.847 (4.3); 7.836 (4.2); 7.829 (4.0); 7.773 (4.6); 7.767 (4.1); 7.755 (5.1); 7.752 (5.5); 7.749 (4.8); 7.746 (4.6); 7.734 (4.8); 7.727 (4.3); 7.519 (8.2); 7.341 (2.4); 7.325 (4.9); 7.320 (4.3); 7.310 (2.0); 7.309 (3.3); 7.304 (9.7); 7.299 (3.2); 7.296 (1.4); 7.292 (4.2); 7.288 (5.3); 7.287 (4.8); 7.286 (2.8); 7.283 (7.0); 7.281 (3.5); 7.280 (2.9); 7.2793 (3.0); 7.2785 (2.8); 7.278 (3.0); 7.277 (3.5); 7.276 (3.9); 7.2753 (4.1); 7.2745 (4.3); 7.274 (4.9); 7.273 (5.2); 7.272 (5.5); 7.2713 (6.4); 7.2705 (6.6); 7.270 (7.4); 7.269 (8.2); 7.268 (10.3); 7.2673 (12.5); 7.2665 (15.5); 7.266 (16.2); 7.265 (18.8); 7.264 (24.5); 7.263 (33.5); 7.260 (1439.5); 7.2544 (9.1); 7.2535 (6.3); 7.253 (5.2); 7.252 (4.1); 7.251 (3.7); 7.2503 (3.2); 7.2495 (2.7); 7.249 (1.7); 7.248 (2.7); 7.247 (1.7); 7.2463 (1.2); 7.2455 (1.1); 7.245 (1.0); 7.244 (1.0); 7.243 (0.9); 7.242 (1.1); 7.240 (0.7); 7.225 (1.5); 7.210 (1.0); 7.190 (3.1); 7.174 (6.0); 7.169 (6.0); 7.158 (3.5); 7.153 (12.5); 7.148 (3.6); 7.137 (5.5); 7.132 (6.5); 7.116 (3.6); 7.020 (5.7); 7.013 (5.7); 6.999 (5.7); 6.996 (9.3); 6.992 (5.5); 6.970 (4.2); 6.966 (9.0); 6.949 (4.7); 6.944 (14.7); 6.940 (4.8); 6.923 (7.7); 6.918 (3.8); 6.870 (7.3); 6.862 (7.3); 6.849 (7.0); 6.841 (6.9); 6.787 (9.6); 6.766 (16.0); 6.744 (8.4); 4.356 (10.3); 4.331 (11.3); 4.279 (13.2); 4.250 (15.2); 3.956 (1.1); 3.923 (2.5); 3.913 (2.6); 3.894 (4.4); 3.884 (4.5); 3.866 (2.2); 3.856 (3.5); 3.847 (2.1); 3.831 (3.1); 3.821 (3.0); 3.806 (1.8); 3.795 (1.8); 3.708 (2.9); 3.582 (2.2); 3.460 (2.6); 3.384 (2.1); 2.574 (1.8); 2.564 (1.9); 2.558 (1.9); 2.549 (2.7); 2.539 (3.3); 2.525 (3.3); 2.515 (3.5); 2.506 (2.1); 2.501 (2.3); 2.491 (1.9); 2.330 (1.5); 2.319 (2.5); 2.291 (2.8); 2.255 (1.6); 2.093 (1.6); 2.066 (2.1); 2.058 (2.3); 2.046 (1.7); 2.031 (2.0); 2.019 (1.1); 1.878 (1.4); 1.866 (1.9); 1.853 (1.9); 1.844 (2.8); 1.830 (2.7); 1.821 (1.5); 1.808 (1.4); 1.795 (1.0); 1.541 (122.4); 1.305 (3.3); 1.228 (2.7); 0.146 (1.4); 0.032 (1.4); 0.022 (0.9); 0.019 (0.9); 0.0144 (1.4); 0.0136 (1.7); 0.013 (1.9); 0.0112 (2.7); 0.0105 (2.8); 0.008 (16.5); 0.007 (5.5); 0.006 (5.6); 0.005 (6.8); 0.004 (8.8); 0.000 (520.2); −0.007 (3.2); −0.009 (13.3); −0.150 (1.5)

[0398]

Example 6:1H-NMR (400.0 MHz, CDCl3): δ=8.522 (15.1); 8.517 (15.2); 8.209 (11.9); 8.204 (12.0); 7.788 (8.7); 7.783 (16.0); 7.778 (8.2); 7.521 (0.7); 7.274 (0.7); 7.272 (0.9); 7.262 (140.8); 7.206 (2.3); 7.190 (4.7); 7.185 (4.4); 7.174 (2.8); 7.169 (9.7); 7.164 (3.0); 7.153 (4.5); 7.148 (5.4); 7.132 (2.7); 6.998 (0.8); 6.808 (8.7); 6.786 (14.6); 6.765 (7.8); 5.299 (14.2); 4.244 (12.2); 4.216 (14.4); 3.922 (2.1); 3.912 (2.2); 3.894 (3.9); 3.884 (3.9); 3.866 (1.9); 3.856 (1.8); 3.749 (2.7); 3.738 (3.2); 3.734 (3.2); 3.723 (5.3); 3.711 (4.0); 3.707 (3.9); 3.696 (3.3); 3.623 (0.5); 3.488 (2.9); 3.475 (3.2); 3.464 (3.4); 3.460 (2.9); 3.452 (3.5); 3.448 (2.9); 3.437 (2.6); 3.425 (2.5); 2.558 (1.3); 2.548 (1.5); 2.543 (1.5); 2.534 (2.2); 2.524 (2.9); 2.513 (2.2); 2.509 (2.9); 2.500 (2.9); 2.490 (1.9); 2.486 (1.8); 2.476 (1.6); 2.340 (0.7); 2.336 (1.2); 2.333 (0.9); 2.325 (2.0); 2.317 (0.9); 2.313 (1.5); 2.308 (1.6); 2.301 (1.8); 2.296 (2.4); 2.291 (2.1); 2.285 (1.7); 2.279 (1.2); 2.274 (1.1); 2.270 (0.6); 2.262 (1.4); 2.254 (0.6); 2.250 (0.8); 1.507 (1.5); 1.432 (0.6); 1.333 (0.6); 1.284 (0.8); 1.255 (0.9); 0.008 (1.7); 0.000 (50.1); −0.009 (1.3)

[0399]

Example 2005:1H-NMR (400.0 MHz, CDCl3): δ=8.519 (9.5); 8.513 (9.5); 8.436 (5.2); 8.432 (7.6); 8.428 (4.9); 8.364 (11.1); 8.358 (11.1); 8.261 (1.9); 8.254 (1.9); 8.146 (2.2); 8.141 (5.8); 8.137 (8.0); 7.520 (3.7); 7.514 (3.4); 7.508 (2.6); 7.498 (2.8); 7.493 (3.4); 7.487 (2.6); 7.425 (3.0); 7.419 (3.8); 7.414 (2.9); 7.403 (3.1); 7.398 (3.8); 7.392 (2.8); 7.280 (0.5); 7.279 (0.5); 7.278 (0.5); 7.2772 (0.6); 7.2765 (0.6); 7.276 (0.7); 7.275 (0.7); 7.274 (0.8); 7.2733 (0.9); 7.2725 (1.0); 7.272 (1.0); 7.271 (1.2); 7.270 (1.4); 7.2693 (1.7); 7.2685 (1.9); 7.268 (2.1); 7.267 (2.6); 7.266 (3.1); 7.265 (4.0); 7.261 (180.7); 7.257 (2.0); 7.2563 (1.3); 7.2555 (0.9); 7.255 (0.6); 7.211 (1.1); 7.197 (1.3); 7.184 (1.4); 7.180 (0.7); 7.174 (3.9); 7.161 (3.4); 7.151 (3.8); 7.148 (1.1); 7.139 (3.3); 7.128 (1.5); 7.116 (1.4); 7.045 (1.5); 7.033 (1.5); 7.022 (3.8); 7.010 (4.0); 7.000 (3.9); 6.997 (2.2); 6.987 (4.3); 6.977 (1.8); 6.974 (1.0); 6.964 (2.3); 6.952 (0.8); 6.939 (1.4); 6.933 (1.5); 6.929 (1.7); 6.924 (1.4); 6.915 (2.3); 6.910 (2.5); 6.906 (2.4); 6.900 (2.3); 6.892 (1.2); 6.886 (1.3); 6.882 (1.1); 6.877 (1.1); 6.774 (1.4); 6.769 (1.6); 6.765 (1.6); 6.759 (1.5); 6.751 (2.5); 6.745 (2.8); 6.741 (2.7); 6.736 (2.5); 6.727 (1.3); 6.722 (1.4); 6.718 (1.3); 6.712 (1.2); 5.298 (16.0); 4.389 (5.4); 4.364 (5.9); 4.307 (5.6); 4.279 (6.5); 3.964 (1.5); 3.954 (1.5); 3.936 (2.8); 3.926 (2.8); 3.908 (1.4); 3.897 (2.3); 3.884 (1.3); 3.870 (2.3); 3.858 (2.3); 3.844 (1.2); 3.832 (1.2); 3.778 (1.9); 3.767 (2.4); 3.764 (2.4); 3.751 (3.5); 3.739 (2.9); 3.736 (2.8); 3.725 (2.3); 3.676 (0.7); 3.664 (1.1); 3.649 (1.2); 3.641 (1.8); 3.636 (0.9); 3.629 (2.3); 3.627 (2.4); 3.615 (3.3); 3.602 (2.7); 3.600 (2.7); 3.589 (2.0); 3.523 (0.5); 3.517 (0.6); 3.503 (0.6); 3.491 (2.2); 3.479 (2.2); 3.468 (2.4); 3.464 (2.0); 3.456 (2.4); 3.452 (2.1); 3.441 (1.8); 3.429 (2.1); 3.426 (2.0); 3.414 (1.9); 3.402 (2.1); 3.398 (1.7); 3.391 (2.1); 3.387 (1.7); 3.376 (1.5); 3.364 (1.5); 3.109 (1.3); 3.093 (1.0); 3.082 (0.8); 2.578 (1.0); 2.568 (1.1); 2.564 (1.1); 2.554 (1.8); 2.544 (2.0); 2.530 (2.0); 2.520 (2.4); 2.510 (1.4); 2.506 (1.3); 2.496 (1.2); 2.336 (0.8); 2.333 (0.6); 2.329 (1.0); 2.325 (1.6); 2.321 (1.0); 2.317 (0.6); 2.313 (1.0); 2.308 (1.0); 2.305 (0.9); 2.301 (1.4); 2.297 (1.9); 2.294 (1.6); 2.290 (1.7); 2.286 (1.4); 2.279 (0.8); 2.274 (0.8); 2.266 (0.7); 2.262 (1.2); 2.258 (0.7); 2.251 (0.6); 2.169 (2.0); 2.108 (1.0); 2.103 (0.8); 2.099 (1.2); 2.095 (1.0); 2.088 (1.1); 2.084 (1.0); 2.076 (1.6); 2.073 (2.0); 2.068 (1.4); 2.065 (1.8); 2.061 (1.6); 2.057 (1.1); 2.053 (1.2); 2.049 (1.1); 2.041 (1.0); 2.038 (1.6); 2.026 (0.7); 1.893 (0.9); 1.880 (1.4); 1.869 (1.4); 1.858 (2.0); 1.845 (1.8); 1.834 (1.0); 1.823 (1.0); 1.810 (0.7); 1.469 (1.3); 0.008 (2.4); 0.007 (0.8); 0.006 (0.9); 0.005 (1.0); 0.004 (1.4); 0.002 (3.4); 0.000 (78.2); −0.005 (1.0); −0.006 (0.7); −0.007 (0.9); −0.009 (2.1); −0.050 (0.5)

[0400]

Example 1834:1H-NMR (400.0 MHz, CDCl3): δ=8.181 (14.2); 8.175 (14.0); 8.141 (9.2); 8.135 (9.2); 7.519 (7.0); 7.515 (4.4); 7.509 (4.0); 7.495 (11.3); 7.488 (11.7); 7.470 (15.3); 7.468 (16.0); 7.449 (6.4); 7.446 (13.4); 7.445 (12.9); 7.425 (17.0); 7.424 (17.3); 7.350 (1.2); 7.336 (0.9); 7.319 (11.2); 7.312 (11.2); 7.298 (8.6); 7.291 (8.5); 7.282 (1.8); 7.277 (2.9); 7.275 (3.6); 7.274 (3.8); 7.272 (4.4); 7.2713 (4.6); 7.2705 (5.4); 7.270 (5.8); 7.269 (6.8); 7.267 (9.5); 7.2664 (10.9); 7.2656 (12.8); 7.260 (1195.3); 7.251 (2.8); 7.228 (2.2); 7.225 (3.1); 7.210 (6.3); 7.204 (4.5); 7.200 (3.8); 7.191 (4.9); 7.171 (2.7); 7.159 (3.0); 7.150 (9.0); 7.143 (6.8); 7.138 (6.5); 7.134 (12.2); 7.127 (5.6); 7.120 (9.9); 7.118 (9.2); 7.114 (7.3); 7.106 (2.5); 7.102 (5.0); 7.098 (7.5); 7.093 (4.7); 7.079 (4.1); 7.074 (5.3); 7.069 (3.5); 7.063 (3.3); 7.060 (3.1); 7.056 (3.7); 7.050 (4.9); 7.044 (3.6); 7.041 (3.7); 7.031 (3.6); 7.028 (4.0); 7.020 (1.7); 7.007 (1.5); 6.996 (6.9); 6.903 (3.6); 6.888 (4.4); 6.884 (4.7); 6.870 (2.6); 4.339 (14.4); 4.322 (15.5); 4.135 (10.8); 4.113 (12.0); 3.796 (3.0); 3.780 (5.6); 3.774 (3.9); 3.758 (7.4); 3.747 (6.8); 3.741 (3.9); 3.733 (6.6); 3.720 (7.9); 3.707 (7.1); 3.693 (5.1); 3.682 (6.2); 3.670 (3.6); 3.665 (5.0); 3.655 (4.8); 3.542 (3.2); 3.529 (3.5); 3.522 (3.7); 3.515 (3.2); 3.509 (3.9); 3.502 (3.0); 3.495 (2.8); 3.482 (2.8); 3.422 (2.1); 3.410 (2.3); 3.399 (2.8); 3.386 (3.0); 3.372 (1.9); 3.360 (1.8); 2.375 (1.4); 2.366 (1.3); 2.361 (1.3); 2.351 (2.1); 2.341 (2.7); 2.326 (2.4); 2.317 (3.4); 2.308 (2.0); 2.303 (2.0); 2.293 (1.7); 2.221 (1.4); 2.209 (2.4); 2.181 (3.0); 2.170 (2.5); 2.146 (4.8); 2.132 (7.8); 2.125 (4.5); 2.119 (6.9); 2.110 (7.5); 2.097 (8.0); 2.085 (3.4); 2.063 (1.1); 1.539 (19.6); 1.345 (1.6); 0.157 (1.0); 0.146 (1.4); 0.008 (14.2); 0.006 (5.2); 0.000 (453.3); −0.009 (12.1); −0.150 (1.4)

[0401]

Example 5:1H-NMR (400.0 MHz, CDCl3): δ=8.593 (12.3); 8.588 (12.6); 8.471 (13.0); 8.466 (13.1); 8.433 (0.7); 8.420 (14.2); 8.415 (14.5); 8.341 (0.6); 8.335 (0.6); 8.182 (1.2); 8.171 (13.3); 8.167 (13.7); 7.744 (7.9); 7.738 (13.9); 7.733 (7.5); 7.640 (8.3); 7.635 (14.9); 7.630 (8.1); 7.520 (0.7); 7.415 (0.6); 7.348 (1.7); 7.332 (3.4); 7.327 (3.5); 7.311 (6.9); 7.306 (2.8); 7.295 (3.6); 7.290 (4.2); 7.274 (3.0); 7.261 (115.5); 7.201 (1.9); 7.185 (3.8); 7.181 (4.0); 7.169 (2.7); 7.164 (7.8); 7.160 (3.0); 7.148 (4.2); 7.143 (4.4); 7.127 (2.2); 6.997 (0.8); 6.972 (9.2); 6.950 (15.0); 6.928 (8.1); 6.818 (0.9); 6.804 (9.8); 6.782 (16.0); 6.760 (8.4); 5.298 (0.8); 4.346 (10.9); 4.321 (12.0); 4.263 (12.4); 4.235 (14.6); 3.927 (2.6); 3.917 (2.7); 3.899 (4.8); 3.889 (4.8); 3.870 (4.2); 3.859 (3.8); 3.843 (3.8); 3.832 (3.8); 3.817 (2.1); 3.805 (2.1); 3.747 (3.1); 3.736 (3.8); 3.733 (3.8); 3.721 (6.2); 3.709 (4.6); 3.706 (4.6); 3.694 (3.8); 3.622 (2.8); 3.610 (3.6); 3.595 (5.7); 3.583 (4.5); 3.569 (3.3); 3.487 (3.4); 3.475 (3.6); 3.464 (4.2); 3.452 (4.2); 3.437 (3.1); 3.424 (4.2); 3.409 (3.3); 3.399 (3.7); 3.387 (3.6); 3.372 (2.5); 3.360 (2.4); 3.063 (0.9); 3.043 (0.7); 2.559 (1.5); 2.549 (1.7); 2.544 (1.8); 2.535 (2.7); 2.525 (3.4); 2.511 (3.4); 2.501 (3.5); 2.492 (2.2); 2.487 (2.1); 2.477 (1.8); 2.337 (1.4); 2.326 (2.5); 2.309 (2.1); 2.297 (3.2); 2.263 (1.8); 2.251 (1.0); 2.112 (1.0); 2.101 (1.8); 2.086 (1.6); 2.074 (2.5); 2.066 (2.9); 2.054 (2.0); 2.039 (2.2); 2.028 (1.2); 1.876 (1.6); 1.862 (2.3); 1.851 (2.2); 1.841 (3.4); 1.828 (3.1); 1.819 (1.8); 1.807 (1.7); 1.793 (1.1); 1.501 (4.0); 1.256 (0.5); 0.007 (1.9); 0.000 (44.2)

[0402]

Example 6: (erythro):1H-NMR (400.0 MHz, CDCl3): δ=8.693 (12.8); 8.688 (13.6); 8.507 (12.5); 8.502 (13.3); 7.888 (8.5); 7.883 (15.5); 7.878 (9.2); 7.520 (0.7); 7.349 (2.4); 7.333 (4.5); 7.328 (4.3); 7.317 (3.3); 7.312 (8.7); 7.307 (4.1); 7.296 (4.5); 7.291 (5.8); 7.275 (3.8); 7.261 (105.8); 7.228 (1.2); 6.997 (1.1); 6.973 (9.8); 6.951 (16.0); 6.929 (8.8); 5.298 (7.5); 4.327 (11.1); 4.302 (12.3); 3.862 (2.3); 3.851 (2.5); 3.836 (4.1); 3.824 (4.3); 3.821 (4.6); 3.811 (2.5); 3.799 (2.4); 3.727 (1.0); 3.623 (2.7); 3.618 (2.2); 3.608 (3.8); 3.596 (5.8); 3.584 (4.5); 3.581 (4.7); 3.570 (3.6); 3.564 (1.7); 3.423 (2.9); 3.410 (3.3); 3.400 (3.8); 3.388 (3.8); 3.384 (3.4); 3.373 (2.8); 3.361 (2.5); 2.112 (1.2); 2.100 (2.0); 2.088 (1.8); 2.084 (1.9); 2.077 (2.5); 2.073 (2.8); 2.069 (2.8); 2.065 (3.2); 2.057 (2.1); 2.053 (2.4); 2.050 (2.3); 2.038 (2.5); 2.026 (1.5); 1.877 (1.7); 1.863 (2.5); 1.852 (2.5); 1.843 (3.6); 1.829 (3.4); 1.821 (2.1); 1.808 (2.0); 1.794 (1.4); 1.476 (1.5); 1.333 (1.2); 1.284 (1.2); 1.256 (1.3); 0.008 (1.7); 0.000 (38.0); −0.009 (2.2)

[0403]

Example 472 (erythro):1H-NMR (400.0 MHz, CDCl3): δ=7.901 (5.1); 7.897 (6.0); 7.893 (5.1); 7.582 (4.3); 7.576 (4.1); 7.561 (4.2); 7.555 (4.0); 7.261 (64.3); 7.187 (2.0); 7.180 (2.3); 7.174 (2.3); 7.166 (4.0); 7.158 (2.3); 7.152 (2.1); 7.144 (2.1); 7.025 (1.1); 7.017 (1.1); 7.015 (1.4); 7.007 (2.1); 7.002 (2.3); 6.995 (2.8); 6.992 (2.5); 6.989 (1.6); 6.984 (3.7); 6.976 (2.4); 6.974 (2.4); 6.966 (2.1); 6.960 (3.3); 6.948 (3.4); 6.937 (4.4); 6.926 (4.3); 6.914 (1.8); 6.903 (1.5); 5.299 (16.0); 4.389 (6.5); 4.373 (6.8); 3.821 (0.8); 3.794 (1.8); 3.781 (3.7); 3.768 (3.8); 3.760 (1.9); 3.754 (4.8); 3.741 (2.7); 3.731 (2.5); 3.710 (2.4); 3.694 (1.2); 3.579 (2.0); 3.567 (2.2); 3.559 (2.3); 3.552 (2.0); 3.546 (2.4); 3.540 (1.9); 3.532 (1.8); 3.519 (1.7); 2.159 (0.7); 2.153 (0.5); 2.145 (0.7); 2.138 (1.9); 2.124 (2.7); 2.117 (3.0); 2.109 (2.2); 2.104 (4.7); 2.090 (2.8); 2.082 (2.9); 2.069 (1.8); 2.057 (0.7); 2.044 (1.1); 1.484 (1.5); 1.432 (0.9); 1.258 (0.8); 0.008 (0.9); 0.000 (23.0); −0.009 (0.8)

[0404]

Example 3:1H-NMR (400.0 MHz, CDCl3): δ=8.339 (3.4); 8.333 (3.3); 8.042 (4.3); 8.035 (4.3); 7.627 (2.2); 7.620 (2.1); 7.606 (4.0); 7.600 (3.9); 7.559 (4.8); 7.558 (4.8); 7.538 (2.6); 7.537 (2.6); 7.523 (3.0); 7.520 (1.1); 7.517 (2.9); 7.503 (4.2); 7.496 (4.1); 7.413 (5.8); 7.412 (5.8); 7.393 (4.0); 7.392 (4.0); 7.341 (0.9); 7.325 (1.6); 7.320 (1.4); 7.309 (1.0); 7.304 (3.2); 7.299 (1.2); 7.288 (1.4); 7.283 (1.9); 7.274 (0.5); 7.267 (2.1); 7.261 (106.6); 7.203 (1.0); 7.187 (2.0); 7.182 (1.9); 7.171 (1.2); 7.166 (4.1); 7.161 (1.3); 7.150 (1.9); 7.145 (2.2); 7.129 (1.1); 6.997 (0.6); 6.970 (1.6); 6.966 (3.4); 6.949 (1.6); 6.944 (5.4); 6.939 (1.7); 6.922 (2.9); 6.918 (1.4); 6.798 (3.8); 6.776 (6.3); 6.755 (3.4); 5.298 (16.0); 4.318 (3.9); 4.293 (4.4); 4.248 (5.0); 4.220 (5.9); 3.919 (0.9); 3.910 (0.9); 3.891 (1.7); 3.881 (1.7); 3.863 (0.8); 3.852 (1.3); 3.840 (0.7); 3.824 (1.3); 3.814 (1.2); 3.799 (0.7); 3.788 (0.7); 3.740 (1.1); 3.730 (1.4); 3.726 (1.4); 3.714 (2.3); 3.702 (1.6); 3.698 (1.6); 3.688 (1.4); 3.618 (0.9); 3.607 (1.1); 3.604 (1.1); 3.592 (1.8); 3.580 (1.4); 3.577 (1.4); 3.565 (1.1); 3.478 (1.2); 3.466 (1.3); 3.455 (1.4); 3.451 (1.2); 3.443 (1.4); 3.439 (1.2); 3.428 (1.1); 3.416 (1.1); 3.410 (1.0); 3.397 (1.0); 3.387 (1.1); 3.383 (0.9); 3.375 (1.1); 3.371 (0.9); 3.360 (0.8); 3.348 (0.8); 2.560 (0.6); 2.551 (0.7); 2.546 (0.7); 2.537 (1.0); 2.527 (1.2); 2.516 (0.9); 2.512 (1.2); 2.502 (1.3); 2.493 (0.9); 2.488 (0.8); 2.478 (0.7); 2.321 (0.6); 2.309 (0.9); 2.297 (0.7); 2.293 (0.7); 2.280 (1.1); 2.270 (0.8); 2.263 (0.5); 2.258 (0.5); 2.246 (0.6); 2.085 (0.6); 2.062 (0.7); 2.058 (0.8); 2.054 (0.7); 2.050 (0.9); 2.047 (0.7); 2.039 (0.6); 2.035 (0.6); 2.023 (0.7); 1.865 (0.5); 1.851 (0.7); 1.840 (0.7); 1.830 (1.1); 1.816 (1.0); 1.806 (0.6); 1.796 (0.6); 1.476 (0.7); 0.008 (1.2); 0.000 (41.0); −0.009 (1.2)

[0405]

Example 1915:1H-NMR (400.0 MHz, CDCl3): δ=8.636 (3.0); 8.632 (3.2); 8.623 (3.2); 8.620 (3.1); 8.583 (3.3); 8.578 (3.4); 8.491 (3.6); 8.487 (3.8); 8.479 (3.8); 475 (3.7); 8.309 (3.6); 8.304 (3.7); 7.762 (1.4); 7.758 (1.7); 7.752 (1.4); 7.742 (1.6); 7.738 (1.7); 7.737 (1.9); 7.732 (1.5); 7.655 (1.5); 7.650 (1.9); 7.645 (1.5); 7.635 (1.7); 7.630 (2.1); 7.625 (1.6); 7.388 (1.9); 7.386 (1.9); 7.376 (1.9); 7.374 (1.9); 7.368 (1.8); 7.366 (1.8); 7.356 (1.7); 7.354 (1.7); 7.264 (53.3); 7.257 (2.7); 7.256 (2.6); 7.245 (2.3); 7.243 (2.3); 7.237 (2.2); 7.236 (2.1); 7.225 (2.0); 7.224 (2.0); 7.004 (2.1); 6.998 (5.3); 6.977 (5.2); 6.970 (2.1); 6.811 (2.0); 6.805 (5.5); 6.784 (5.5); 6.777 (2.0); 5.299 (16.0); 4.292 (3.5); 4.267 (3.8); 4.215 (3.9); 4.187 (4.7); 3.912 (0.8); 3.903 (0.9); 3.884 (1.5); 3.874 (1.5); 3.856 (0.8); 3.846 (0.8); 3.835 (0.7); 3.824 (0.8); 3.809 (1.2); 3.798 (1.2); 3.783 (0.7); 3.772 (0.7); 3.749 (0.6); 3.736 (1.0); 3.723 (1.2); 3.709 (1.1); 3.696 (0.7); 3.602 (0.5); 3.589 (0.8); 3.576 (1.0); 3.563 (1.0); 3.550 (0.6); 3.473 (0.6); 3.462 (0.7); 3.448 (0.9); 3.438 (0.9); 3.425 (0.6); 3.412 (0.5); 3.393 (0.6); 3.380 (0.6); 3.368 (0.8); 3.358 (0.8); 3.344 (0.5); 2.557 (0.5); 2.547 (0.6); 2.542 (0.6); 2.533 (0.9); 2.523 (1.1); 2.508 (1.1); 2.498 (1.1); 2.489 (0.7); 2.485 (0.7); 2.475 (0.6); 2.285 (0.8); 2.274 (0.6); 2.269 (0.6); 2.261 (0.7); 2.257 (1.0); 2.251 (0.9); 2.246 (0.7); 2.222 (0.6); 2.057 (0.6); 2.033 (0.7); 2.030 (0.8); 2.026 (0.7); 2.022 (0.9); 2.018 (0.7); 2.010 (0.6); 2.007 (0.6); 1.995 (0.7); 1.865 (0.5); 1.852 (0.7); 1.840 (0.7); 1.830 (1.1); 1.817 (1.0); 1.808 (0.5); 1.795 (0.5); 1.676 (0.7); 1.664 (0.7); 1.612 (1.0); 1.517 (0.7); 0.008 (0.5); 0.000 (18.1); −0.009 (0.6)

[0406]

Example 1961:1H-NMR (400.0 MHz, CDCl3): δ=8.169 (14.3); 8.162 (14.3); 8.127 (9.5); 8.120 (9.6); 7.588 (6.7); 7.582 (6.6); 7.568 (7.7); 7.561 (7.5); 7.519 (4.3); 7.442 (4.1); 7.438 (4.4); 7.424 (8.1); 7.419 (8.7); 7.405 (5.0); 7.401 (5.0); 7.385 (7.8); 7.379 (7.6); 7.364 (10.5); 7.358 (10.3); 7.310 (1.6); 7.307 (3.1); 7.303 (3.4); 7.294 (3.8); 7.289 (6.7); 7.287 (5.1); 7.284 (6.2); 7.281 (13.5); 7.275 (7.3); 7.273 (6.3); 7.271 (8.5); 7.268 (11.9); 7.260 (814.9); 7.255 (29.0); 7.246 (4.7); 7.244 (5.4); 7.241 (4.2); 7.233 (15.1); 7.224 (4.0); 7.218 (2.5); 7.209 (9.4); 7.206 (8.7); 7.190 (10.9); 7.187 (11.5); 7.172 (4.7); 7.168 (4.3); 7.114 (1.0); 7.109 (1.5); 7.095 (5.3); 7.089 (4.9); 7.087 (5.3); 7.082 (11.6); 7.080 (10.0); 7.073 (5.1); 7.068 (6.2); 7.066 (6.1); 7.047 (1.5); 7.025 (4.1); 7.023 (3.7); 7.005 (3.8); 7.002 (3.8); 6.996 (7.9); 6.977 (3.6); 6.969 (6.2); 6.966 (6.2); 6.949 (5.4); 6.946 (6.4); 6.944 (7.0); 6.940 (6.4); 6.923 (5.3); 6.920 (5.1); 5.298 (3.6); 4.342 (15.2); 4.326 (16.0); 4.161 (9.9); 4.139 (10.9); 3.765 (2.9); 3.746 (7.6); 3.728 (8.3); 3.710 (5.4); 3.694 (3.1); 3.668 (2.4); 3.650 (3.7); 3.640 (3.6); 3.627 (2.3); 3.621 (3.1); 3.611 (2.7); 3.599 (2.4); 3.589 (2.2); 3.528 (3.1); 3.401 (1.9); 2.386 (1.2); 2.377 (1.2); 2.371 (1.3); 2.362 (1.9); 2.352 (2.4); 2.342 (2.0); 2.337 (2.4); 2.328 (2.6); 2.319 (2.0); 2.314 (1.9); 2.304 (1.8); 2.244 (1.1); 2.234 (2.2); 2.219 (1.4); 2.205 (2.3); 2.196 (1.7); 2.170 (1.7); 2.148 (6.3); 2.131 (10.9); 2.117 (10.2); 2.113 (8.7); 2.099 (5.8); 2.005 (0.6); 1.545 (84.7); 1.330 (4.2); 1.244 (2.4); 0.146 (1.0); 0.069 (1.8); 0.050 (0.5); 0.008 (8.7); 0.006 (3.1); 0.005 (3.3); 0.000 (316.2); −0.006 (3.1); −0.007 (2.7); −0.009 (9.2); −0.016 (0.7); −0.150 (0.9)

[0407]

Example 1873:1H-NMR (400.0 MHz, CDCl3): δ=8.606 (1.4); 8.594 (1.7); 8.587 (2.1); 8.581 (2.1); 8.568 (8.6); 8.564 (9.2); 8.556 (9.6); 8.552 (9.5); 8.527 (7.1); 8.523 (7.7); 8.515 (7.8); 8.511 (7.7); 8.468 (0.5); 8.433 (10.7); 8.428 (10.9); 8.396 (8.6); 8.390 (8.8); 8.360 (1.0); 8.339 (0.7); 7.736 (1.0); 7.735 (1.0); 7.730 (0.8); 7.717 (1.1); 7.715 (1.1); 7.711 (0.8); 7.659 (3.6); 7.654 (4.7); 7.649 (3.6); 7.639 (3.9); 7.634 (5.1); 7.629 (3.8); 7.522 (1.5); 7.466 (4.1); 7.461 (5.6); 7.456 (4.3); 7.446 (5.0); 7.441 (6.6); 7.436 (4.7); 7.366 (1.7); 7.354 (1.6); 7.346 (1.5); 7.336 (1.2); 7.296 (1.6); 7.289 (5.9); 7.287 (6.2); 7.277 (6.8); 7.275 (7.3); 7.267 (10.2); 7.263 (254.9); 7.255 (8.6); 7.249 (8.0); 7.248 (7.9); 7.242 (6.9); 7.240 (6.8); 7.228 (8.5); 7.221 (3.3); 7.217 (3.3); 7.213 (6.6); 7.204 (4.0); 7.197 (3.8); 7.194 (5.2); 7.189 (3.7); 7.161 (3.0); 7.148 (3.2); 7.146 (3.1); 7.140 (6.0); 7.138 (6.5); 7.125 (10.1); 7.121 (9.1); 7.108 (8.1); 7.102 (7.4); 7.096 (5.4); 7.091 (2.8); 7.087 (4.2); 7.083 (5.4); 7.079 (4.8); 7.071 (3.9); 7.066 (4.5); 7.063 (4.0); 7.058 (2.6); 7.053 (4.0); 7.047 (5.4); 7.042 (6.1); 7.028 (6.6); 7.024 (7.1); 7.021 (4.9); 7.011 (4.4); 7.009 (4.4); 7.004 (2.1); 6.999 (2.8); 6.988 (2.0); 6.928 (2.3); 6.924 (3.6); 6.921 (2.5); 6.914 (2.4); 6.909 (3.7); 6.905 (4.7); 6.897 (1.9); 6.891 (2.5); 6.886 (1.6); 5.298 (16.0); 4.354 (12.8); 4.337 (13.5); 4.224 (0.7); 4.206 (0.7); 4.151 (9.7); 4.130 (10.8); 4.080 (0.5); 4.048 (0.6); 4.027 (0.5); 3.808 (3.0); 3.791 (5.4); 3.781 (8.2); 3.775 (3.9); 3.769 (5.8); 3.753 (3.2); 3.742 (3.3); 3.737 (3.9); 3.733 (3.7); 3.724 (7.4); 3.711 (9.7); 3.705 (4.0); 3.697 (8.5); 3.684 (6.8); 3.675 (3.5); 3.664 (5.3); 3.653 (3.8); 3.648 (3.7); 3.637 (3.3); 3.603 (0.8); 3.566 (1.5); 3.530 (3.7); 3.516 (3.9); 3.511 (4.3); 3.503 (3.5); 3.497 (4.2); 3.489 (3.3); 3.484 (3.4); 3.470 (3.1); 3.422 (2.7); 3.410 (3.0); 3.399 (3.3); 3.396 (2.9); 3.387 (3.2); 3.383 (2.9); 3.373 (2.5); 3.360 (2.3); 2.384 (1.2); 2.374 (1.3); 2.368 (1.4); 2.359 (1.8); 2.349 (2.5); 2.339 (2.2); 2.334 (2.5); 2.325 (2.9); 2.316 (2.2); 2.311 (2.1); 2.301 (1.9); 2.237 (1.4); 2.226 (2.5); 2.211 (1.7); 2.198 (2.7); 2.188 (2.1); 2.181 (1.6); 2.163 (2.2); 2.146 (3.7); 2.137 (3.7); 2.131 (6.0); 2.125 (7.9); 2.111 (7.8); 2.102 (6.1); 2.097 (3.9); 2.089 (3.5); 2.067 (1.2); 2.053 (0.9); 1.630 (4.5); 1.256 (0.9); 1.246 (0.8); 0.008 (2.6); 0.000 (85.9); −0.009 (3.0)

[0408]

Example 1 (threo):1H-NMR (400.0 MHz, CDCl3): δ=7.893 (9.0); 7.887 (9.7); 7.774 (4.6); 7.767 (4.2); 7.756 (5.1); 7.753 (5.6); 7.749 (5.0); 7.746 (4.9); 7.734 (4.7); 7.728 (4.3); 7.521 (0.8); 7.275 (0.5); 7.274 (0.5); 7.273 (0.7); 7.272 (0.7); 7.2712 (0.8); 7.2705 (1.0); 7.270 (1.1); 7.269 (1.3); 7.268 (1.5); 7.267 (1.8); 7.262 (128.4); 7.255 (0.6); 7.190 (2.7); 7.174 (5.6); 7.169 (5.3); 7.158 (3.2); 7.153 (11.5); 7.148 (3.6); 7.136 (5.3); 7.132 (6.3); 7.115 (3.1); 6.998 (0.8); 6.870 (7.3); 6.863 (7.4); 6.849 (7.0); 6.841 (6.9); 6.787 (9.6); 6.765 (16.0); 6.744 (8.5); 5.299 (3.6); 4.281 (13.0); 4.252 (15.1); 3.924 (2.4); 3.914 (2.5); 3.896 (4.6); 3.886 (4.6); 3.867 (2.2); 3.858 (2.1); 3.746 (3.2); 3.735 (3.8); 3.731 (3.9); 3.719 (6.5); 3.708 (4.7); 3.704 (4.6); 3.693 (4.1); 3.487 (3.5); 3.474 (3.8); 3.464 (4.1); 3.460 (3.4); 3.451 (4.1); 3.447 (3.6); 3.436 (3.2); 3.424 (3.1); 2.571 (1.6); 2.561 (1.8); 2.556 (1.8); 2.547 (2.6); 2.537 (3.3); 2.534 (2.1); 2.527 (2.5); 2.522 (3.3); 2.513 (3.4); 2.504 (2.3); 2.499 (2.1); 2.489 (1.9); 2.333 (0.8); 2.330 (1.4); 2.326 (1.0); 2.318 (2.2); 2.310 (1.0); 2.306 (1.8); 2.302 (1.8); 2.295 (2.0); 2.289 (2.7); 2.285 (2.5); 2.279 (2.0); 2.272 (1.5); 2.267 (1.3); 2.263 (0.8); 2.255 (1.6); 2.247 (0.7); 2.244 (1.0); 2.240 (0.6); 1.495 (2.9); 1.333 (0.6); 1.284 (0.9); 1.276 (0.6); 1.262 (0.6); 1.256 (1.2); 0.008 (1.5); 0.006 (0.6); 0.000 (45.7); −0.009 (1.2)

[0409]

Example 2:1H-NMR (400.0 MHz, CDCl3): δ=8.358 (10.0); 8.352 (9.9); 8.058 (11.7); 8.052 (11.7); 7.730 (7.4); 7.724 (7.3); 7.710 (8.3); 7.703 (8.0); 7.627 (8.6); 7.620 (8.4); 7.606 (9.6); 7.600 (9.3); 7.519 (4.6); 7.405 (10.8); 7.384 (9.7); 7.373 (2.0); 7.342 (1.6); 7.326 (3.7); 7.321 (3.4); 7.310 (3.1); 7.305 (8.5); 7.300 (2.8); 7.294 (1.6); 7.288 (3.6); 7.284 (5.2); 7.260 (826.1); 7.238 (12.7); 7.228 (1.2); 7.209 (1.6); 7.200 (2.4); 7.184 (5.3); 7.179 (5.1); 7.167 (2.9); 7.162 (10.4); 7.158 (3.3); 7.146 (3.2); 7.141 (5.3); 7.125 (2.7); 6.996 (4.6); 6.967 (8.5); 6.945 (14.1); 6.923 (7.5); 6.919 (3.9); 6.796 (9.6); 6.774 (16.0); 6.752 (8.4); 5.299 (1.9); 4.337 (9.9); 4.313 (11.1); 4.266 (12.6); 4.237 (14.9); 3.922 (2.4); 3.912 (2.5); 3.893 (4.4); 3.884 (4.4); 3.865 (2.2); 3.856 (3.6); 3.845 (1.9); 3.829 (3.1); 3.818 (3.1); 3.804 (1.8); 3.793 (1.7); 3.746 (1.7); 3.731 (2.5); 3.719 (3.4); 3.707 (3.1); 3.693 (2.1); 3.608 (2.1); 3.595 (2.6); 3.582 (2.8); 3.569 (1.7); 3.447 (2.6); 3.420 (1.8); 3.388 (2.1); 2.567 (1.6); 2.557 (1.6); 2.552 (1.8); 2.543 (2.7); 2.533 (3.1); 2.518 (3.1); 2.509 (3.4); 2.500 (2.2); 2.495 (2.0); 2.485 (1.8); 2.326 (1.3); 2.314 (2.3); 2.285 (2.7); 2.251 (1.6); 2.090 (1.6); 2.055 (2.4); 2.040 (1.5); 2.028 (1.8); 2.016 (1.0); 2.005 (0.7); 1.869 (1.3); 1.856 (1.9); 1.844 (1.9); 1.835 (2.8); 1.821 (2.6); 1.812 (1.4); 1.799 (1.4); 1.786 (0.9); 1.540 (37.1); 1.300 (2.4); 1.227 (1.9); 0.157 (0.8); 0.146 (0.9); 0.113 (0.7); 0.008 (9.3); 0.000 (314.2); −0.009 (9.1); −0.051 (0.8); −0.150 (1.1)

[0410]

Example 472 (erythro):1H-NMR (400.0 MHz, CDCl3): δ=7.901 (5.1); 7.897 (6.0); 7.893 (5.1); 7.582 (4.3); 7.576 (4.1); 7.561 (4.2); 7.555 (4.0); 7.261 (64.3); 7.187 (2.0); 7.180 (2.3); 7.174 (2.3); 7.166 (4.0); 7.158 (2.3); 7.152 (2.1); 7.144 (2.1); 7.025 (1.1); 7.017 (1.1); 7.015 (1.4); 7.007 (2.1); 7.002 (2.3); 6.995 (2.8); 6.992 (2.5); 6.989 (1.6); 6.984 (3.7); 6.976 (2.4); 6.974 (2.4); 6.966 (2.1); 6.960 (3.3); 6.948 (3.4); 6.937 (4.4); 6.926 (4.3); 6.914 (1.8); 6.903 (1.5); 5.299 (16.0); 4.389 (6.5); 4.373 (6.8); 3.821 (0.8); 3.794 (1.8); 3.781 (3.7); 3.768 (3.8); 3.760 (1.9); 3.754 (4.8); 3.741 (2.7); 3.731 (2.5); 3.710 (2.4); 3.694 (1.2); 3.579 (2.0); 3.567 (2.2); 3.559 (2.3); 3.552 (2.0); 3.546 (2.4); 3.540 (1.9); 3.532 (1.8); 3.519 (1.7); 2.159 (0.7); 2.153 (0.5); 2.145 (0.7); 2.138 (1.9); 2.124 (2.7); 2.117 (3.0); 2.109 (2.2); 2.104 (4.7); 2.090 (2.8); 2.082 (2.9); 2.069 (1.8); 2.057 (0.7); 2.044 (1.1); 1.484 (1.5); 1.432 (0.9); 1.258 (0.8); 0.008 (0.9); 0.000 (23.0); −0.009 (0.8)

[0411]

Example 472 (threo):1H-NMR (400.0 MHz, CDCl3): δ=7.860 (11.4); 7.855 (14.7); 7.852 (13.0); 7.791 (12.3); 7.786 (10.6); 7.771 (12.1); 7.765 (10.7); 7.520 (1.3); 7.311 (0.5); 7.297 (0.9); 7.261 (212.8); 7.034 (3.4); 7.022 (3.9); 7.011 (9.6); 6.999 (9.9); 6.987 (8.1); 6.982 (5.9); 6.975 (11.5); 6.971 (6.6); 6.964 (9.9); 6.959 (3.5); 6.956 (6.0); 6.953 (6.9); 6.946 (5.7); 6.941 (4.2); 6.934 (2.9); 6.931 (2.1); 6.923 (2.2); 6.871 (5.0); 6.863 (4.7); 6.857 (5.4); 6.849 (9.0); 6.842 (4.9); 6.836 (5.2); 6.828 (4.3); 5.299 (5.5); 4.158 (14.7); 4.136 (16.0); 3.736 (4.3); 3.726 (5.2); 3.722 (5.4); 3.710 (7.4); 3.699 (6.2); 3.695 (6.0); 3.685 (5.1); 3.652 (3.3); 3.643 (3.5); 3.631 (3.7); 3.623 (5.8); 3.615 (4.0); 3.603 (3.6); 3.594 (3.5); 3.439 (4.7); 3.428 (5.4); 3.416 (6.1); 3.413 (5.5); 3.404 (6.1); 3.401 (5.6); 3.389 (4.5); 3.377 (4.2); 2.370 (2.2); 2.361 (2.4); 2.355 (2.5); 2.346 (4.3); 2.335 (4.5); 2.325 (3.8); 2.321 (4.5); 2.311 (6.0); 2.302 (3.5); 2.297 (3.2); 2.287 (2.8); 2.192 (2.0); 2.189 (2.1); 2.179 (3.7); 2.170 (2.4); 2.167 (2.4); 2.163 (2.4); 2.160 (2.4); 2.152 (4.2); 2.142 (3.8); 2.128 (1.7); 2.116 (2.5); 2.106 (1.4); 1.454 (1.6); 1.333 (1.4); 1.284 (1.4); 1.256 (1.9); 0.008 (2.7); 0.000 (76.0); −0.009 (2.9)

[0412]

Example 543:1H-NMR (400.0 MHz, CDCl3): δ=8.573 (10.8); 8.569 (11.0); 8.561 (11.2); 8.557 (10.8); 8.535 (0.5); 8.531 (0.6); 8.523 (0.6); 8.519 (0.5); 8.449 (12.5); 8.444 (12.2); 8.405 (0.5); 8.399 (0.6); 7.520 (2.4); 7.493 (4.7); 7.488 (6.3); 7.483 (4.6); 7.473 (5.7); 7.468 (7.4); 7.463 (5.2); 7.345 (0.7); 7.293 (1.0); 7.261 (436.3); 7.255 (2.7); 7.252 (8.1); 7.250 (7.7); 7.244 (6.5); 7.242 (6.4); 7.232 (6.2); 7.230 (5.8); 7.159 (4.4); 7.151 (4.9); 7.145 (4.7); 7.137 (8.4); 7.129 (4.9); 7.123 (4.6); 7.116 (4.6); 6.997 (2.6); 6.987 (2.5); 6.979 (2.5); 6.977 (3.1); 6.969 (4.6); 6.964 (5.6); 6.961 (2.9); 6.957 (6.0); 6.954 (5.6); 6.951 (3.3); 6.946 (9.2); 6.939 (5.9); 6.936 (5.5); 6.928 (10.3); 6.916 (7.0); 6.904 (9.7); 6.893 (9.4); 6.882 (3.5); 6.870 (3.2); 5.299 (2.3); 4.334 (15.1); 4.316 (16.0); 4.148 (0.6); 4.127 (0.7); 3.760 (2.2); 3.743 (8.0); 3.730 (10.1); 3.716 (10.4); 3.703 (11.2); 3.690 (5.2); 3.679 (0.5); 3.536 (4.5); 3.522 (4.6); 3.516 (5.0); 3.509 (4.1); 3.502 (5.1); 3.496 (3.7); 3.489 (3.9); 3.475 (3.7); 2.148 (0.7); 2.133 (1.3); 2.112 (3.8); 2.098 (8.5); 2.092 (4.3); 2.084 (8.6); 2.078 (6.4); 2.072 (5.2); 2.062 (7.3); 2.049 (3.3); 2.038 (1.0); 2.027 (1.2); 2.013 (0.5); 1.576 (7.4); 0.008 (5.0); 0.0063 (1.8); 0.0055 (2.1); 0.000 (145.6); −0.005 (1.2); −0.006 (1.0); −0.007 (0.9); −0.009 (3.9)

[0413]

Example 460 (erythro):1H-NMR (400.0 MHz, CDCl3): δ=8.209 (15.4); 8.203 (15.2); 7.521 (0.6); 7.433 (8.3); 7.427 (8.2); 7.413 (10.9); 7.406 (10.5); 7.363 (0.5); 7.313 (0.6); 7.280 (18.3); 7.262 (95.6); 7.215 (1.3); 7.175 (4.7); 7.167 (5.4); 7.161 (5.3); 7.153 (8.6); 7.145 (5.3); 7.139 (4.9); 7.131 (4.7); 7.000 (2.1); 6.992 (2.2); 6.990 (2.6); 6.982 (4.0); 6.977 (4.9); 6.970 (6.1); 6.967 (5.5); 6.964 (3.8); 6.959 (7.9); 6.952 (5.5); 6.949 (5.7); 6.943 (8.8); 6.931 (7.3); 6.920 (9.3); 6.909 (9.0); 6.898 (3.8); 6.886 (3.3); 5.299 (0.7); 4.359 (15.1); 4.342 (16.0); 3.768 (3.8); 3.755 (9.3); 3.742 (10.0); 3.728 (13.8); 3.715 (10.1); 3.697 (3.1); 3.554 (4.5); 3.541 (5.0); 3.533 (5.3); 3.527 (4.7); 3.520 (5.5); 3.514 (4.4); 3.506 (4.2); 3.493 (3.9); 2.158 (0.7); 2.144 (1.5); 2.138 (1.0); 2.123 (4.0); 2.108 (6.7); 2.103 (6.9); 2.090 (10.1); 2.079 (6.4); 2.068 (7.0); 2.056 (4.4); 2.044 (1.9); 2.033 (2.0); 2.020 (1.1); 1.531 (10.9); 1.284 (0.5); 1.255 (1.1); 0.008 (1.7); 0.000 (34.5); −0.008 (1.8)

[0414]

Example 460 (threo):1H-NMR (400.0 MHz, CDCl3): δ=8.159 (13.6); 8.153 (13.8); 7.620 (9.8); 7.613 (9.6); 7.599 (11.3); 7.593 (11.0); 7.520 (1.0); 7.324 (0.6); 7.317 (16.0); 7.316 (15.9); 7.296 (13.9); 7.295 (14.1); 7.261 (186.4); 7.011 (2.7); 6.999 (3.2); 6.998 (2.1); 6.988 (8.3); 6.976 (8.4); 6.965 (6.7); 6.960 (5.0); 6.953 (10.5); 6.949 (5.8); 6.942 (9.2); 6.937 (2.7); 6.934 (5.1); 6.931 (6.1); 6.926 (2.3); 6.923 (5.1); 6.919 (3.7); 6.911 (2.4); 6.908 (1.8); 6.901 (2.0); 6.854 (4.4); 6.847 (4.1); 6.840 (4.6); 6.833 (8.0); 6.825 (4.2); 6.819 (4.6); 6.812 (3.7); 4.146 (14.6); 4.124 (16.0); 3.717 (3.6); 3.706 (4.3); 3.702 (4.4); 3.690 (6.7); 3.679 (5.3); 3.675 (5.2); 3.665 (4.7); 3.656 (2.9); 3.646 (2.9); 3.634 (2.9); 3.626 (4.8); 3.618 (3.2); 3.605 (2.8); 3.596 (2.7); 3.429 (4.4); 3.417 (5.0); 3.406 (5.3); 3.402 (4.6); 3.394 (5.3); 3.390 (4.9); 3.379 (4.2); 3.367 (4.0); 2.369 (1.8); 2.359 (1.9); 2.354 (2.0); 2.345 (3.4); 2.334 (3.5); 2.330 (2.4); 2.324 (3.0); 2.319 (3.5); 2.310 (4.8); 2.301 (2.8); 2.295 (2.6); 2.286 (2.4); 2.187 (1.5); 2.184 (1.6); 2.174 (2.9); 2.165 (1.7); 2.162 (1.9); 2.159 (1.8); 2.156 (1.8); 2.146 (3.3); 2.137 (2.9); 2.130 (1.4); 2.127 (1.4); 2.124 (1.4); 2.121 (1.3); 2.111 (2.0); 2.101 (1.1); 2.098 (1.1); 1.482 (5.6); 1.333 (0.8); 1.284 (1.1); 1.255 (2.6); 0.008 (2.1); 0.0064 (0.7); 0.0055 (0.7); 0.005 (0.9); 0.004 (1.2); 0.000 (70.8); −0.006 (1.1); −0.007 (1.0); −0.008 (2.3)

[0415]

Example 2003:1H-NMR (400.0 MHz, CDCl3): δ=8.372 (11.9); 8.365 (11.9); 8.078 (12.4); 8.072 (12.6); 7.743 (8.5); 7.737 (8.5); 7.722 (9.7); 7.716 (9.6); 7.650 (9.3); 7.643 (9.1); 7.629 (10.7); 7.623 (10.3); 7.519 (5.1); 7.423 (13.1); 7.403 (11.6); 7.294 (16.1); 7.279 (1.9); 7.273 (16.0); 7.272 (16.7); 7.269 (6.2); 7.268 (6.6); 7.2674 (6.9); 7.2665 (8.1); 7.266 (10.0); 7.265 (12.2); 7.260 (902.5); 7.254 (6.6); 7.253 (5.5); 7.252 (4.3); 7.251 (3.4); 7.2503 (3.1); 7.2496 (2.8); 7.249 (2.2); 7.248 (2.1); 7.247 (2.0); 7.246 (2.0); 7.245 (1.7); 7.236 (1.1); 7.234 (1.0); 7.229 (1.9); 7.210 (2.0); 7.193 (2.4); 7.180 (2.5); 7.170 (6.4); 7.157 (5.4); 7.147 (5.6); 7.135 (5.4); 7.125 (2.3); 7.112 (2.4); 7.051 (2.5); 7.039 (2.6); 7.028 (6.4); 7.016 (6.4); 7.006 (6.5); 6.996 (6.3); 6.993 (6.6); 6.983 (2.7); 6.971 (2.7); 6.935 (2.4); 6.929 (2.6); 6.925 (2.6); 6.920 (2.7); 6.911 (4.3); 6.906 (4.4); 6.902 (4.2); 6.896 (4.0); 6.888 (2.2); 6.882 (2.2); 6.878 (2.1); 6.873 (1.9); 6.773 (2.3); 6.767 (2.5); 6.763 (2.5); 6.758 (2.5); 6.749 (4.0); 6.743 (4.5); 6.740 (4.4); 6.734 (4.0); 6.725 (2.2); 6.720 (2.3); 6.716 (2.2); 6.711 (2.1); 5.299 (2.4); 4.336 (12.0); 4.311 (13.4); 4.262 (13.5); 4.234 (16.0); 3.949 (2.6); 3.940 (2.7); 3.921 (4.8); 3.912 (4.9); 3.892 (2.4); 3.883 (2.4); 3.869 (2.2); 3.857 (2.5); 3.843 (3.8); 3.832 (4.0); 3.817 (2.1); 3.805 (2.1); 3.775 (3.0); 3.761 (3.9); 3.749 (5.6); 3.737 (4.7); 3.734 (4.7); 3.723 (3.9); 3.639 (2.6); 3.626 (3.6); 3.613 (5.4); 3.599 (4.6); 3.587 (3.5); 3.486 (3.3); 3.474 (3.7); 3.462 (4.1); 3.451 (4.1); 3.436 (3.1); 3.424 (3.2); 3.418 (3.0); 3.406 (3.1); 3.395 (3.4); 3.383 (3.5); 3.368 (2.6); 3.356 (2.4); 2.578 (1.6); 2.568 (1.7); 2.564 (1.9); 2.555 (3.0); 2.544 (3.4); 2.530 (3.4); 2.520 (4.0); 2.510 (2.4); 2.506 (2.2); 2.496 (1.9); 2.321 (1.4); 2.310 (2.8); 2.294 (1.7); 2.282 (3.1); 2.275 (2.9); 2.271 (2.5); 2.247 (2.1); 2.082 (1.8); 2.070 (1.4); 2.055 (2.5); 2.051 (2.2); 2.047 (2.9); 2.032 (1.7); 2.021 (2.3); 2.005 (1.2); 1.882 (1.5); 1.869 (2.4); 1.857 (2.4); 1.847 (3.6); 1.834 (3.4); 1.822 (1.9); 1.811 (1.8); 1.798 (1.3); 1.530 (6.4); 0.331 (0.8); 0.238 (0.6); 0.157 (1.1); 0.146 (1.0); 0.034 (0.6); 0.008 (10.4); 0.000 (351.7); −0.009 (9.7); −0.050 (0.6); −0.150 (1.1)

[0416]

Example 2006:1H-NMR (400.0 MHz, CDCl3): δ=8.613 (10.9); 8.607 (10.9); 8.485 (10.6); 8.479 (10.8); 8.457 (13.4); 8.451 (13.3); 8.331 (1.2); 8.325 (1.2); 8.186 (10.2); 8.181 (10.3); 7.756 (6.3); 7.751 (11.5); 7.746 (5.9); 7.667 (7.1); 7.661 (12.7); 7.656 (6.7); 7.518 (9.1); 7.471 (1.0); 7.359 (0.8); 7.347 (0.7); 7.340 (0.7); 7.323 (0.7); 7.312 (0.8); 7.294 (2.1); 7.286 (2.2); 7.259 (1642.2); 7.253 (7.4); 7.252 (5.6); 7.251 (4.0); 7.2504 (3.1); 7.2496 (2.9); 7.249 (2.5); 7.248 (2.4); 7.247 (1.8); 7.2464 (2.1); 7.2456 (1.8); 7.245 (1.3); 7.244 (1.5); 7.243 (1.3); 7.2424 (1.4); 7.2416 (1.2); 7.241 (1.1); 7.240 (1.1); 7.239 (1.1); 7.238 (0.8); 7.237 (0.8); 7.235 (1.0); 7.227 (1.0); 7.218 (0.7); 7.215 (0.7); 7.210 (2.7); 7.209 (2.2); 7.200 (1.9); 7.187 (1.7); 7.177 (4.1); 7.171 (1.8); 7.164 (4.6); 7.154 (5.1); 7.146 (5.0); 7.142 (5.8); 7.131 (4.1); 7.119 (4.0); 7.055 (2.0); 7.042 (1.9); 7.032 (4.7); 7.019 (4.9); 7.009 (5.1); 6.996 (12.9); 6.986 (2.7); 6.974 (3.3); 6.961 (1.4); 6.950 (1.4); 6.942 (2.4); 6.936 (2.8); 6.932 (2.8); 927 (3.1); 6.918 (4.6); 6.913 (5.2); 6.909 (5.0); 6.903 (5.1); 6.895 (3.9); 6.889 (4.0); 6.885 (3.6); 6.880 (3.5); 6.812 (1.1); 6.783 (2.2); 6.774 (1.9); 6.768 (2.1); 6.760 (3.0); 6.754 (3.2); 6.750 (3.2); 6.745 (2.8); 6.736 (1.7); 6.731 (1.5); 6.721 (1.7); 6.708 (1.2); 6.696 (0.8); 6.667 (1.2); 5.298 (16.0); 4.392 (1.2); 4.382 (1.3); 4.341 (8.1); 4.316 (9.1); 4.259 (9.8); 4.231 (11.5); 4.113 (1.1); 3.951 (2.2); 3.940 (2.0); 3.922 (3.5); 3.913 (3.7); 3.895 (2.1); 3.883 (2.7); 3.870 (1.9); 3.855 (3.2); 3.844 (3.2); 3.829 (2.2); 3.817 (2.2); 3.781 (3.5); 3.767 (3.7); 3.754 (4.8); 3.742 (4.6); 3.728 (4.3); 3.697 (5.0); 3.682 (6.8); 3.666 (5.2); 3.643 (3.3); 3.631 (3.7); 3.617 (4.2); 3.603 (3.6); 3.591 (2.8); 3.494 (3.2); 3.481 (3.5); 3.469 (4.0); 3.458 (4.3); 3.442 (4.2); 3.430 (4.9); 3.417 (4.0); 3.406 (4.4); 3.379 (3.6); 3.368 (3.3); 3.285 (1.9); 3.246 (1.8); 3.216 (1.8); 3.124 (1.7); 3.039 (1.3); 2.976 (1.3); 2.899 (1.3); 2.824 (2.3); 2.806 (2.9); 2.786 (2.3); 2.624 (1.5); 2.573 (2.2); 2.563 (2.3); 2.549 (3.1); 2.539 (3.5); 2.524 (3.3); 2.514 (3.6); 2.505 (2.7); 2.491 (2.1); 2.324 (3.4); 2.295 (3.5); 2.261 (2.5); 2.169 (2.3); 2.094 (3.6); 2.067 (3.4); 2.059 (3.8); 2.045 (3.7); 2.033 (4.2); 1.903 (2.5); 1.887 (4.1); 1.877 (3.1); 1.866 (4.6); 1.855 (4.2); 1.841 (3.5); 1.833 (2.8); 1.819 (2.6); 1.807 (2.2); 1.583 (4.0); 1.333 (2.5); 1.256 (8.0); 1.217 (1.9); 1.202 (1.3); 1.085 (0.8); 0.880 (1.0); 0.146 (1.9); 0.125 (2.1); 0.035 (0.7); 0.015 (1.8); 0.008 (20.0); 0.000 (699.5); −0.009 (19.0); −0.033 (0.7); −0.051 (1.3); −0.114 (1.2); −0.150 (1.9)

[0417]

Example 2001:1H-NMR (400.0 MHz, CDCl3): δ=8.556 (11.0); 8.552 (11.4); 8.544 (11.4); 8.540 (11.3); 8.504 (7.7); 8.500 (8.2); 8.492 (8.2); 8.488 (8.0); 8.418 (12.3); 8.412 (12.3); 8.380 (8.7); 8.375 (8.7); 7.642 (3.6); 7.637 (4.7); 7.632 (3.5); 7.622 (3.9); 7.617 (5.1); 7.612 (3.8); 7.520 (2.5); 7.458 (4.5); 7.453 (6.2); 7.448 (4.6); 7.438 (6.3); 7.434 (10.2); 7.416 (8.4); 7.411 (8.8); 7.397 (5.1); 7.393 (5.1); 7.374 (0.9); 7.295 (3.4); 7.291 (3.4); 7.282 (3.6); 7.277 (7.1); 7.275 (5.5); 7.272 (6.5); 7.270 (6.3); 7.261 (467.8); 7.252 (6.2); 7.247 (8.0); 7.242 (13.5); 7.239 (13.9); 7.234 (3.6); 7.229 (15.6); 7.225 (5.4); 7.222 (9.6); 7.220 (7.5); 7.216 (3.7); 7.213 (3.7); 7.208 (11.1); 7.204 (4.0); 7.200 (8.3); 7.196 (10.1); 7.191 (3.7); 7.181 (11.1); 7.178 (11.5); 7.162 (4.7); 7.159 (4.6); 7.133 (2.2); 7.129 (2.4); 7.114 (5.2); 7.110 (5.1); 7.096 (4.6); 7.091 (3.8); 7.073 (6.5); 7.070 (7.2); 7.055 (6.7); 7.052 (7.1); 7.036 (2.7); 7.033 (3.0); 7.014 (4.7); 7.011 (4.2); 6.997 (2.9); 6.993 (4.1); 6.990 (3.9); 6.987 (4.7); 6.984 (4.2); 6.966 (3.8); 6.963 (3.7); 6.955 (6.0); 6.952 (6.1); 6.935 (5.5); 6.932 (6.2); 6.930 (6.9); 6.926 (6.3); 6.909 (5.3); 6.906 (5.2); 5.298 (2.3); 4.330 (15.0); 4.312 (16.0); 4.166 (10.1); 4.145 (11.1); 3.769 (2.7); 3.751 (6.2); 3.732 (6.2); 3.715 (5.6); 3.702 (7.5); 3.688 (8.7); 3.675 (12.6); 3.668 (4.2); 3.662 (6.9); 3.652 (8.3); 3.642 (5.4); 3.636 (6.1); 3.625 (5.1); 3.615 (2.3); 3.525 (4.4); 3.508 (6.7); 3.498 (3.8); 3.491 (4.8); 3.481 (5.5); 3.464 (3.5); 3.430 (3.0); 3.417 (3.4); 3.408 (3.5); 3.403 (2.8); 3.394 (3.5); 3.390 (3.1); 3.381 (2.8); 3.368 (2.7); 2.381 (1.2); 2.371 (1.3); 2.365 (1.3); 2.358 (1.4); 2.356 (1.7); 2.346 (2.6); 2.336 (2.2); 2.331 (2.5); 2.324 (2.6); 2.321 (2.4); 2.314 (2.1); 2.308 (1.9); 2.298 (1.9); 2.265 (1.3); 2.262 (1.3); 2.251 (2.5); 2.241 (1.4); 2.237 (1.7); 2.223 (2.5); 2.212 (1.6); 2.209 (1.4); 2.202 (1.0); 2.188 (1.4); 2.175 (0.7); 2.133 (6.1); 2.120 (9.3); 2.115 (10.1); 2.100 (10.6); 2.084 (5.7); 1.583 (3.2); 1.255 (0.5); 0.069 (2.5); 0.008 (5.1); 0.000 (162.6); −0.009 (4.2)

[0418]

Example 15 (threo):1H-NMR (400.0 MHz, CDCl3): δ=8.109 (2.4); 8.001 (2.4); 7.934 (6.0); 7.928 (5.9); 7.915 (5.3); 7.909 (5.9); 7.805 (7.4); 7.518 (15.8); 7.321 (3.0); 7.292 (6.5); 7.259 (2865.7); 7.210 (8.9); 7.191 (6.8); 7.175 (3.1); 7.170 (3.5); 7.154 (2.3); 6.995 (16.0); 6.954 (3.7); 6.933 (2.3); 6.826 (7.3); 6.805 (11.3); 6.783 (6.3); 4.358 (2.4); 4.334 (3.0); 4.264 (8.9); 4.236 (10.4); 3.921 (2.7); 3.876 (3.4); 3.739 (3.1); 3.727 (3.7); 3.712 (3.1); 3.457 (3.2); 2.500 (2.8); 2.312 (2.3); 2.282 (2.3); 2.043 (2.5); 1.532 (919.9); 1.484 (2.6); 1.315 (4.6); 1.300 (6.8); 1.289 (4.8); 1.258 (3.6); 0.882 (2.3); 0.146 (3.6); 0.008 (40.0); 0.000 (1113.5); −0.009 (40.0); −0.050 (3.4); −0.149 (4.0)

[0419]

Example 463:1H-NMR (400.0 MHz, CDCl3): δ=8.529 (15.9); 8.524 (16.0); 8.496 (9.9); 8.491 (9.9); 8.309 (14.4); 8.304 (14.6); 8.273 (8.4); 8.268 (8.6); 7.653 (5.7); 7.648 (9.7); 7.643 (5.0); 7.520 (1.1); 7.457 (7.5); 7.452 (13.8); 7.446 (7.2); 7.276 (0.5); 7.275 (0.6); 7.274 (0.6); 7.2723 (0.8); 7.2715 (0.8); 7.271 (1.0); 7.270 (1.1); 7.2683 (1.6); 7.2675 (1.7); 7.261 (204.4); 7.171 (3.3); 7.163 (3.6); 7.157 (3.6); 7.149 (6.5); 7.141 (3.7); 7.135 (3.5); 7.127 (3.5); 7.027 (1.6); 7.015 (1.9); 7.012 (2.2); 7.004 (5.2); 6.997 (2.1); 6.992 (5.1); 6.990 (5.0); 6.987 (2.4); 6.982 (5.3); 6.980 (6.9); 6.976 (2.7); 6.972 (7.2); 6.969 (6.4); 6.964 (4.5); 6.961 (6.3); 6.959 (3.4); 6.953 (4.1); 6.950 (6.6); 6.943 (3.0); 6.940 (3.8); 6.938 (6.1); 6.933 (3.1); 6.926 (7.7); 6.921 (1.9); 6.915 (7.2); 6.910 (1.6); 6.903 (2.7); 6.892 (2.5); 6.875 (2.2); 6.868 (2.0); 6.861 (2.3); 6.854 (4.0); 6.846 (2.0); 6.840 (2.3); 6.832 (1.8); 5.298 (5.4); 4.361 (12.1); 4.344 (12.7); 4.154 (7.5); 4.133 (8.2); 3.757 (3.8); 3.741 (5.4); 3.733 (4.9); 3.718 (5.7); 3.702 (2.8); 3.679 (1.6); 3.666 (2.3); 3.657 (1.6); 3.645 (1.5); 3.637 (2.6); 3.628 (1.6); 3.617 (1.5); 3.607 (1.4); 3.530 (2.2); 3.404 (1.5); 3.379 (0.8); 2.352 (0.9); 2.343 (1.0); 2.337 (1.0); 2.328 (1.6); 2.317 (1.8); 2.314 (1.2); 2.308 (1.6); 2.302 (1.8); 2.293 (2.4); 2.284 (1.5); 2.279 (1.4); 2.269 (1.3); 2.202 (0.8); 2.200 (0.8); 2.190 (1.6); 2.180 (0.9); 2.177 (1.0); 2.174 (0.9); 2.171 (1.0); 2.168 (1.2); 2.159 (1.8); 2.152 (1.5); 2.149 (1.1); 2.144 (1.4); 2.139 (1.1); 2.123 (3.3); 2.109 (6.1); 2.103 (3.5); 2.094 (6.7); 2.087 (4.7); 2.084 (3.9); 2.073 (6.0); 2.059 (2.6); 2.049 (0.7); 2.038 (0.9); 1.578 (3.9); 1.457 (3.1); 1.367 (1.7); 0.069 (0.5); 0.008 (2.3); 0.0063 (0.7); 0.0055 (0.7); 0.005 (0.9); 0.004 (1.2); 0.000 (81.5); −0.005 (1.6); −0.006 (1.3); −0.007 (1.1); −0.009 (2.6); −0.011 (0.5)

[0420]

Example 1876:1H-NMR (400.0 MHz, CDCl3): δ=8.336 (9.4); 8.331 (9.1); 8.066 (9.8); 8.060 (10.0); 7.618 (5.0); 7.611 (4.3); 7.597 (11.1); 7.591 (11.7); 7.569 (14.1); 7.567 (14.2); 7.549 (5.8); 7.522 (6.2); 7.519 (11.8); 7.516 (6.1); 7.502 (10.0); 7.495 (10.2); 7.447 (14.2); 7.428 (8.0); 7.360 (1.7); 7.350 (1.5); 7.299 (1.8); 7.292 (2.3); 7.288 (2.4); 7.260 (1963.6); 7.210 (5.1); 7.012 (6.4); 7.005 (15.5); 6.996 (11.2); 6.984 (15.0); 6.977 (5.6); 6.850 (5.4); 6.844 (16.0); 6.823 (16.0); 6.816 (5.1); 4.278 (9.6); 4.253 (11.1); 4.204 (10.5); 4.176 (12.4); 3.992 (1.3); 3.892 (2.0); 3.883 (2.0); 3.865 (3.8); 3.854 (3.8); 3.837 (2.0); 3.827 (1.9); 3.812 (1.9); 3.800 (2.0); 3.785 (3.1); 3.774 (3.1); 3.759 (3.4); 3.748 (4.0); 3.732 (4.1); 3.720 (3.6); 3.706 (2.6); 3.635 (1.9); 3.623 (3.0); 3.609 (3.6); 3.595 (3.5); 3.583 (2.5); 3.470 (2.0); 3.458 (2.2); 3.445 (2.6); 3.435 (2.8); 3.419 (2.2); 3.409 (3.0); 3.386 (2.6); 3.375 (2.5); 3.361 (1.7); 3.349 (1.6); 2.547 (1.3); 2.532 (1.5); 2.522 (2.7); 2.512 (3.0); 2.498 (2.7); 2.488 (3.2); 2.479 (2.1); 2.464 (1.6); 2.264 (2.3); 2.236 (2.4); 2.201 (1.7); 2.052 (1.6); 2.017 (2.5); 2.005 (2.0); 1.991 (1.7); 1.869 (1.6); 1.856 (2.2); 1.845 (2.2); 1.834 (3.0); 1.821 (2.6); 1.799 (1.6); 1.536 (69.1); 1.284 (1.5); 0.157 (1.3); 0.146 (2.1); 0.008 (21.0); 0.000 (750.9); −0.009 (21.8); −0.050 (2.0); −0.150 (2.6)

[0421]

Example 1836:1H-NMR (400.0 MHz, CDCl3): δ=8.537 (12.8); 8.531 (13.0); 8.498 (8.3); 8.492 (8.5); 8.298 (10.9); 8.293 (11.0); 8.268 (7.0); 8.263 (7.2); 7.654 (4.3); 7.649 (8.0); 7.643 (4.1); 7.519 (2.3); 7.448 (5.8); 7.443 (10.7); 7.438 (5.8); 7.309 (0.7); 7.292 (0.8); 7.269 (2.9); 7.260 (420.0); 7.254 (2.7); 7.253 (2.1); 7.252 (1.9); 7.2503 (1.1); 7.2495 (0.8); 7.249 (0.9); 7.248 (0.9); 7.247 (0.8); 7.2463 (0.7); 7.2455 (0.7); 7.244 (0.7); 7.242 (0.5); 7.232 (1.3); 7.227 (1.8); 7.214 (3.7); 7.210 (3.3); 7.205 (2.7); 7.196 (3.2); 7.191 (2.8); 7.184 (2.6); 7.172 (2.3); 7.163 (5.8); 7.154 (5.1); 7.152 (4.8); 7.149 (4.9); 7.146 (7.9); 7.137 (4.0); 7.131 (9.0); 7.125 (4.5); 7.117 (1.9); 7.113 (3.4); 7.108 (3.5); 7.105 (2.8); 7.101 (2.5); 7.093 (1.7); 7.087 (2.6); 7.081 (3.0); 7.076 (2.1); 7.073 (2.1); 7.070 (1.8); 7.064 (2.3); 7.058 (4.1); 7.054 (2.3); 7.050 (2.4); 7.041 (2.3); 7.038 (2.4); 7.033 (1.1); 7.030 (1.2); 7.017 (1.1); 6.996 (2.4); 6.928 (2.1); 6.913 (2.5); 6.909 (2.7); 6.900 (1.0); 6.895 (1.5); 5.299 (16.0); 4.370 (9.1); 4.353 (9.5); 4.162 (5.9); 4.141 (6.5); 3.804 (2.0); 3.788 (3.7); 3.783 (3.0); 3.771 (2.8); 3.766 (4.6); 3.749 (3.4); 3.731 (3.4); 3.721 (3.2); 3.710 (2.9); 3.701 (3.5); 3.693 (2.8); 3.681 (2.8); 3.672 (2.7); 3.531 (1.9); 3.425 (1.0); 3.400 (1.4); 3.175 (1.3); 2.891 (1.4); 2.889 (1.4); 2.364 (0.7); 2.355 (0.8); 2.350 (0.7); 2.340 (1.1); 2.330 (1.5); 2.320 (1.4); 2.315 (1.6); 2.306 (1.9); 2.296 (1.2); 2.291 (1.2); 2.282 (1.0); 2.238 (0.8); 2.228 (1.5); 2.215 (0.9); 2.200 (1.4); 2.174 (1.0); 2.170 (1.3); 2.164 (1.1); 2.153 (2.6); 2.143 (2.5); 2.139 (3.6); 2.132 (4.7); 2.118 (4.9); 2.109 (4.0); 2.096 (2.3); 2.074 (0.8); 1.555 (8.5); 1.387 (2.6); 1.294 (1.8); 0.008 (4.8); 0.000 (165.4); −0.009 (4.8)

[0422]

Example 6 (erythro):1H-NMR (400.0 MHz, CDCl3): δ=8.693 (12.8); 8.688 (13.6); 8.507 (12.5); 8.502 (13.3); 7.888 (8.5); 7.883 (15.5); 7.878 (9.2); 7.520 (0.7); 7.349 (2.4); 7.333 (4.5); 7.328 (4.3); 7.317 (3.3); 7.312 (8.7); 7.307 (4.1); 7.296 (4.5); 7.291 (5.8); 7.275 (3.8); 7.261 (105.8); 7.228 (1.2); 6.997 (1.1); 6.973 (9.8); 6.951 (16.0); 6.929 (8.8); 5.298 (7.5); 4.327 (11.1); 4.302 (12.3); 3.862 (2.3); 3.851 (2.5); 3.836 (4.1); 3.824 (4.3); 3.821 (4.6); 3.811 (2.5); 3.799 (2.4); 3.727 (1.0); 3.623 (2.7); 3.618 (2.2); 3.608 (3.8); 3.596 (5.8); 3.584 (4.5); 3.581 (4.7); 3.570 (3.6); 3.564 (1.7); 3.423 (2.9); 3.410 (3.3); 3.400 (3.8); 3.388 (3.8); 3.384 (3.4); 3.373 (2.8); 3.361 (2.5); 2.112 (1.2); 2.100 (2.0); 2.088 (1.8); 2.084 (1.9); 2.077 (2.5); 2.073 (2.8); 2.069 (2.8); 2.065 (3.2); 2.057 (2.1); 2.053 (2.4); 2.050 (2.3); 2.038 (2.5); 2.026 (1.5); 1.877 (1.7); 1.863 (2.5); 1.852 (2.5); 1.843 (3.6); 1.829 (3.4); 1.821 (2.1); 1.808 (2.0); 1.794 (1.4); 1.476 (1.5); 1.333 (1.2); 1.284 (1.2); 1.256 (1.3); 0.008 (1.7); 0.000 (38.0); −0.009 (2.2)

[0423]

Example 472 (erythro):1H-NMR (400.0 MHz, CDCl3): δ=7.898 (1.5); 7.860 (11.3); 7.855 (14.3); 7.852 (12.8); 7.791 (12.5); 7.785 (10.6); 7.771 (12.3); 7.765 (10.6); 7.581 (1.0); 7.575 (1.0); 7.561 (1.0); 7.555 (1.0); 7.519 (2.2); 7.310 (1.0); 7.291 (1.7); 7.275 (2.3); 7.271 (3.5); 7.269 (4.2); 7.260 (392.8); 7.247 (1.5); 7.246 (1.4); 7.189 (0.6); 7.181 (0.7); 7.174 (0.7); 7.167 (0.9); 7.159 (0.6); 7.145 (0.6); 7.034 (3.3); 7.022 (4.0); 7.011 (9.7); 6.999 (10.2); 6.988 (8.3); 6.982 (6.1); 6.975 (11.8); 6.972 (6.7); 6.964 (10.3); 6.960 (3.9); 6.957 (6.0); 6.953 (6.9); 6.946 (5.8); 6.942 (4.3); 6.937 (1.9); 6.934 (2.9); 6.931 (2.1); 6.924 (2.4); 6.915 (0.6); 6.904 (0.5); 6.870 (5.0); 6.863 (4.7); 6.856 (5.3); 6.849 (9.0); 6.842 (4.7); 6.835 (5.1); 6.828 (4.1); 5.299 (0.5); 4.387 (1.4); 4.371 (1.6); 4.157 (14.8); 4.135 (16.0); 3.796 (0.6); 3.783 (0.9); 3.770 (1.0); 3.756 (1.3); 3.737 (4.4); 3.727 (5.4); 3.723 (5.3); 3.711 (7.6); 3.700 (6.0); 3.696 (5.9); 3.686 (5.0); 3.652 (3.2); 3.643 (3.6); 3.629 (4.2); 3.623 (5.6); 3.615 (3.9); 3.602 (3.5); 3.593 (3.2); 3.569 (0.6); 3.561 (0.6); 3.554 (0.6); 3.548 (0.6); 3.542 (0.5); 3.534 (0.5); 3.440 (4.5); 3.428 (5.2); 3.416 (5.9); 3.414 (5.1); 3.405 (5.8); 3.402 (5.4); 3.390 (4.3); 3.378 (4.0); 2.370 (2.3); 2.361 (2.4); 2.356 (2.5); 2.346 (4.2); 2.336 (4.4); 2.326 (3.7); 2.321 (4.4); 2.312 (6.0); 2.302 (3.4); 2.297 (3.2); 2.288 (2.8); 2.189 (2.2); 2.180 (3.6); 2.170 (2.4); 2.167 (2.4); 2.163 (2.4); 2.153 (4.2); 2.142 (3.9); 2.126 (2.0); 2.117 (2.8); 2.106 (2.2); 2.091 (0.7); 2.083 (0.7); 1.510 (2.2); 1.333 (1.4); 1.284 (1.3); 1.256 (1.8); 0.008 (5.1); 0.000 (138.5); −0.008 (4.5)

[0424]

Example 1963:1H-NMR (400.0 MHz, CDCl3): δ=8.417 (15.9); 8.411 (16.0); 8.369 (14.0); 8.362 (14.2); 8.247 (7.9); 8.243 (12.9); 8.239 (8.0); 8.203 (6.9); 8.199 (11.5); 8.196 (7.0); 7.520 (1.1); 7.451 (3.3); 7.447 (3.6); 7.433 (6.7); 7.428 (7.0); 7.414 (4.0); 7.410 (4.1); 7.378 (3.9); 7.372 (5.2); 7.366 (3.7); 7.356 (3.9); 7.350 (5.3); 7.344 (3.7); 7.312 (2.4); 7.307 (2.4); 7.298 (2.4); 7.293 (5.0); 7.291 (3.6); 7.289 (3.9); 7.287 (3.3); 7.280 (4.3); 7.278 (3.6); 7.275 (4.6); 7.273 (6.2); 7.268 (6.0); 7.261 (206.1); 7.255 (5.7); 7.248 (3.9); 7.244 (3.4); 7.242 (3.1); 7.236 (2.8); 7.233 (2.9); 7.231 (3.6); 7.228 (4.7); 7.224 (3.4); 7.216 (7.8); 7.214 (7.3); 7.210 (3.8); 7.198 (8.7); 7.195 (9.2); 7.179 (3.8); 7.176 (3.7); 7.166 (4.0); 7.161 (5.6); 7.155 (3.9); 7.144 (4.0); 7.139 (5.6); 7.132 (5.3); 7.127 (2.5); 7.113 (5.1); 7.108 (5.1); 7.096 (5.6); 7.087 (7.7); 7.085 (7.8); 7.070 (6.6); 7.067 (7.4); 7.051 (2.5); 7.048 (2.7); 7.031 (4.7); 7.028 (4.7); 7.011 (4.1); 7.008 (4.0); 7.004 (4.7); 7.002 (4.3); 6.997 (1.6); 6.983 (3.8); 6.981 (3.6); 6.965 (4.8); 6.962 (4.8); 6.944 (4.5); 6.941 (5.1); 6.939 (5.6); 6.935 (5.1); 6.918 (4.1); 6.915 (4.2); 4.399 (10.9); 4.382 (11.5); 4.212 (9.2); 4.190 (9.9); 3.787 (2.3); 3.769 (5.4); 3.750 (5.8); 3.733 (5.5); 3.719 (3.8); 3.706 (4.5); 3.693 (3.6); 3.676 (4.0); 3.667 (5.6); 3.654 (4.8); 3.648 (4.5); 3.639 (3.8); 3.626 (2.6); 3.616 (2.4); 3.548 (1.8); 3.532 (3.4); 3.515 (2.4); 3.505 (2.7); 3.489 (1.5); 3.431 (1.4); 3.418 (1.6); 3.407 (2.2); 3.395 (2.3); 3.383 (1.4); 3.369 (1.2); 2.380 (1.2); 2.370 (1.3); 2.365 (1.3); 2.355 (1.7); 2.346 (2.7); 2.336 (2.3); 2.330 (2.7); 2.322 (2.9); 2.313 (2.2); 2.307 (2.1); 2.298 (1.9); 2.265 (1.3); 2.262 (1.3); 2.252 (2.5); 2.241 (1.4); 2.238 (1.7); 2.233 (1.4); 2.223 (2.5); 2.217 (1.8); 2.213 (1.8); 2.210 (1.4); 2.202 (1.0); 2.188 (1.4); 2.178 (0.8); 2.175 (0.9); 2.155 (5.2); 2.141 (7.5); 2.137 (8.7); 2.123 (8.7); 2.106 (4.8); 2.004 (0.5); 1.597 (2.1); 1.465 (2.2); 1.373 (1.7); 0.008 (2.3); 0.000 (76.6); −0.009 (2.2)

[0425]

Example 1833:1H-NMR (400.0 MHz, CDCl3): δ=8.197 (15.2); 8.191 (15.2); 8.156 (11.3); 8.149 (11.4); 7.617 (7.7); 7.610 (7.6); 7.596 (8.8); 7.589 (8.6); 7.519 (5.3); 7.421 (8.3); 7.415 (8.2); 7.401 (11.0); 7.394 (11.0); 7.315 (13.3); 7.295 (11.1); 7.294 (11.4); 7.291 (3.5); 7.287 (19.1); 7.286 (18.8); 7.276 (2.5); 7.275 (2.7); 7.273 (3.4); 7.267 (20.9); 7.265 (24.7); 7.260 (966.2); 7.230 (2.4); 7.227 (3.9); 7.213 (7.1); 7.209 (4.6); 7.205 (3.7); 7.195 (5.6); 7.172 (3.2); 7.160 (3.2); 7.150 (8.3); 7.142 (7.4); 7.139 (7.0); 7.134 (13.4); 7.125 (5.6); 7.119 (13.3); 7.113 (6.2); 7.105 (2.5); 7.101 (5.3); 7.096 (6.0); 7.090 (4.6); 7.087 (2.3); 7.081 (2.6); 7.076 (5.1); 7.071 (5.7); 7.066 (3.8); 7.061 (3.6); 7.058 (3.6); 7.053 (4.1); 7.047 (7.2); 7.042 (4.1); 7.039 (4.3); 7.029 (3.9); 7.026 (4.4); 7.018 (2.1); 7.005 (1.8); 6.996 (5.6); 6.904 (4.1); 6.893 (2.8); 6.889 (5.0); 6.885 (5.1); 6.875 (1.9); 6.870 (2.7); 4.362 (15.4); 4.346 (16.0); 4.153 (11.5); 4.131 (12.7); 3.799 (3.2); 3.783 (5.9); 3.777 (4.1); 3.767 (4.6); 3.761 (7.6); 3.745 (5.6); 3.718 (5.7); 3.709 (5.6); 3.696 (4.7); 3.689 (5.7); 3.680 (5.2); 3.668 (5.0); 3.658 (4.0); 3.518 (2.9); 3.393 (2.5); 2.381 (1.4); 2.372 (1.5); 2.367 (1.5); 2.358 (2.4); 2.347 (2.8); 2.337 (2.4); 2.332 (2.9); 2.323 (3.6); 2.314 (2.1); 2.309 (1.9); 2.299 (1.9); 2.224 (1.4); 2.212 (2.4); 2.184 (2.8); 2.173 (2.8); 2.158 (2.0); 2.151 (4.8); 2.137 (8.7); 2.131 (4.8); 2.124 (7.6); 2.116 (7.8); 2.102 (8.3); 2.090 (3.5); 2.068 (1.1); 1.546 (81.8); 1.359 (4.3); 1.273 (3.2); 0.146 (1.0); 0.008 (10.2); 0.000 (370.0); −0.009 (10.2); −0.150 (1.0)

[0426]

Example 2004:1H-NMR (400.0 MHz, CDCl3): δ=8.354 (11.7); 8.348 (11.5); 8.061 (11.1); 8.055 (11.2); 7.641 (6.0); 7.634 (5.8); 7.620 (12.0); 7.613 (11.7); 7.577 (15.8); 7.557 (7.9); 7.546 (6.9); 7.540 (6.8); 7.525 (10.4); 7.519 (16.0); 7.448 (15.1); 7.427 (9.8); 7.355 (0.9); 7.295 (1.9); 7.260 (1050.3); 7.211 (2.2); 7.193 (2.5); 7.181 (2.6); 7.170 (5.7); 7.158 (5.4); 7.148 (5.4); 7.135 (5.5); 7.125 (2.4); 7.113 (2.2); 7.055 (2.1); 7.043 (2.1); 7.032 (5.5); 7.020 (5.5); 7.010 (5.7); 6.996 (9.3); 6.987 (2.4); 6.974 (2.0); 6.935 (2.4); 6.926 (3.2); 6.920 (2.7); 6.911 (4.1); 6.906 (4.4); 6.902 (4.5); 6.896 (4.1); 6.888 (2.3); 6.882 (2.5); 6.873 (2.0); 6.775 (2.2); 6.769 (2.3); 6.760 (2.3); 6.752 (3.5); 6.746 (4.2); 6.743 (4.1); 6.736 (3.7); 6.728 (2.2); 6.722 (2.4); 6.713 (1.9); 4.314 (12.0); 4.289 (13.1); 4.244 (11.8); 4.216 (14.0); 3.946 (2.4); 3.937 (2.5); 3.919 (4.7); 3.909 (4.7); 3.890 (2.1); 3.880 (2.3); 3.864 (2.5); 3.853 (2.7); 3.838 (4.2); 3.827 (4.4); 3.812 (2.3); 3.801 (2.2); 3.761 (2.9); 3.746 (3.6); 3.734 (3.5); 3.721 (2.2); 3.624 (3.0); 3.611 (3.7); 3.598 (3.6); 3.585 (2.5); 3.449 (3.1); 3.416 (2.4); 3.405 (2.3); 3.391 (3.0); 3.381 (3.1); 2.575 (1.4); 2.561 (2.0); 2.551 (2.9); 2.540 (3.5); 2.526 (2.9); 2.516 (3.5); 2.507 (2.0); 2.492 (2.0); 2.306 (2.6); 2.278 (2.9); 2.243 (1.9); 2.077 (2.0); 2.042 (2.7); 2.016 (2.1); 1.876 (1.6); 1.863 (2.5); 1.851 (2.8); 1.841 (4.0); 1.828 (3.5); 1.816 (2.0); 1.805 (2.0); 1.540 (60.1); 1.320 (2.5); 1.242 (2.3); 0.146 (1.5); 0.008 (15.3); 0.000 (387.3); −0.009 (11.3); −0.150 (1.3)

[0427]

Example 460 (threo):1H-NMR (400.0 MHz, CDCl3): δ=8.159 (12.2); 8.153 (12.3); 7.620 (8.2); 7.614 (8.0); 7.600 (9.4); 7.593 (9.2); 7.521 (0.6); 7.316 (14.0); 7.296 (12.2); 7.262 (87.8); 7.213 (0.8); 7.011 (2.4); 6.999 (2.9); 6.988 (7.0); 6.976 (7.1); 6.964 (6.0); 6.960 (4.2); 6.952 (8.9); 6.949 (4.9); 6.941 (7.3); 6.937 (2.6); 6.934 (4.5); 6.930 (5.2); 6.923 (4.3); 6.919 (3.2); 6.911 (2.3); 6.908 (1.8); 6.901 (1.8); 6.855 (3.8); 6.847 (3.6); 6.841 (4.1); 6.833 (6.8); 6.826 (3.7); 6.819 (4.0); 6.812 (3.3); 5.299 (16.0); 4.147 (12.4); 4.125 (13.6); 3.716 (3.1); 3.705 (3.8); 3.701 (3.8); 3.690 (5.9); 3.678 (4.7); 3.674 (4.6); 3.664 (4.2); 3.656 (2.9); 3.647 (2.9); 3.634 (2.8); 3.627 (4.5); 3.619 (3.1); 3.606 (2.7); 3.597 (2.6); 3.428 (3.7); 3.416 (4.2); 3.405 (4.6); 3.402 (4.0); 3.393 (4.7); 3.390 (4.3); 3.378 (3.7); 3.366 (3.5); 2.368 (1.5); 2.359 (1.7); 2.353 (1.7); 2.344 (2.9); 2.333 (3.1); 2.324 (2.7); 2.319 (3.2); 2.309 (4.2); 2.300 (2.6); 2.295 (2.4); 2.285 (2.1); 2.184 (1.5); 2.174 (2.7); 2.161 (1.8); 2.158 (1.7); 2.156 (1.7); 2.146 (3.1); 2.137 (2.6); 2.127 (1.4); 2.123 (1.4); 2.111 (2.0); 2.101 (1.1); 2.098 (1.1); 1.496 (6.0); 1.333 (0.5); 1.284 (0.7); 1.255 (1.3); 0.008 (1.2); 0.000 (33.9); −0.009 (1.3)

[0428]

Example 460 (erythro):1H-NMR (400.0 MHz, CDCl3): δ=8.207 (14.7); 8.201 (15.0); 7.520 (0.7); 7.432 (8.1); 7.426 (8.1); 7.412 (10.7); 7.405 (10.5); 7.362 (0.5); 7.311 (0.7); 7.279 (18.0); 7.262 (108.2); 7.229 (1.0); 7.211 (1.4); 7.174 (4.3); 7.167 (4.8); 7.161 (4.7); 7.153 (8.2); 7.145 (4.9); 7.139 (4.7); 7.131 (4.6); 7.000 (1.9); 6.992 (2.0); 6.990 (2.5); 6.982 (3.8); 6.977 (4.6); 6.970 (5.7); 6.967 (5.2); 6.964 (3.2); 6.959 (7.8); 6.952 (5.0); 6.949 (5.3); 6.943 (8.2); 6.931 (7.0); 6.920 (9.2); 6.909 (9.0); 6.897 (3.6); 6.886 (3.2); 5.299 (1.0); 4.357 (15.1); 4.340 (16.0); 3.768 (3.7); 3.755 (8.8); 3.741 (9.3); 3.735 (5.9); 3.728 (13.4); 3.715 (9.4); 3.696 (2.9); 3.553 (4.3); 3.541 (4.7); 3.533 (5.0); 3.527 (4.3); 3.520 (5.2); 3.514 (4.1); 3.506 (4.0); 3.493 (3.8); 2.158 (0.7); 2.143 (1.4); 2.122 (3.8); 2.108 (6.1); 2.102 (6.5); 2.089 (9.4); 2.079 (5.8); 2.068 (6.6); 2.055 (4.1); 2.044 (1.7); 2.032 (1.8); 2.020 (1.0); 1.500 (10.9); 1.255 (1.0); 0.008 (1.3); 0.000 (39.9); −0.008 (1.8)

[0429]

Example 6 (threo):1H-NMR (400.0 MHz, CDCl3): δ=8.696 (0.8); 8.691 (0.8); 8.522 (15.6); 8.517 (15.8); 8.510 (1.2); 8.505 (0.9); 8.208 (12.2); 8.203 (12.3); 7.884 (0.9); 7.788 (8.7); 7.783 (16.0); 7.777 (8.2); 7.520 (1.0); 7.313 (0.6); 7.295 (0.6); 7.293 (0.5); 7.275 (0.8); 7.261 (176.3); 7.206 (2.3); 7.190 (4.7); 7.185 (4.4); 7.174 (2.7); 7.169 (9.6); 7.164 (3.0); 7.153 (4.4); 7.148 (5.3); 7.132 (2.6); 6.997 (1.0); 6.974 (0.5); 952 (0.9); 6.808 (8.7); 6.786 (14.5); 6.764 (7.7); 5.299 (6.2); 4.329 (0.6); 4.304 (0.7); 4.243 (12.2); 4.215 (14.5); 3.921 (2.1); 3.912 (2.2); 3.893 (3.9); 3.883 (3.9); 3.865 (2.0); 3.855 (1.9); 3.750 (2.6); 3.739 (3.1); 3.735 (3.1); 3.723 (5.1); 3.712 (3.8); 3.708 (3.7); 3.697 (3.2); 3.619 (2.1); 3.567 (0.8); 3.488 (2.7); 3.476 (3.0); 3.465 (3.0); 3.461 (2.7); 3.453 (3.3); 3.449 (2.8); 3.438 (2.5); 3.426 (2.4); 2.558 (1.3); 2.548 (1.5); 2.543 (1.5); 2.534 (2.2); 2.524 (2.9); 2.514 (2.2); 2.509 (2.9); 2.500 (2.9); 2.491 (1.9); 2.486 (1.8); 2.476 (1.6); 2.340 (0.7); 2.337 (1.2); 2.333 (0.9); 2.325 (2.0); 2.317 (0.9); 2.313 (1.5); 2.309 (1.6); 2.296 (2.3); 2.291 (2.1); 2.285 (1.7); 2.279 (1.2); 2.274 (1.1); 2.262 (1.4); 2.251 (0.8); 1.516 (1.2); 1.333 (0.8); 1.284 (1.0); 1.256 (1.1); 0.008 (2.0); 0.000 (62.2); −0.009 (1.6)

[0430]

Example 85:1H-NMR (400.0 MHz, CDCl3): δ=8.640 (4.8); 8.630 (5.0); 8.601 (5.8); 8.460 (5.6); 8.456 (5.9); 8.448 (5.8); 8.444 (5.6); 8.413 (0.6); 8.295 (7.5); 8.290 (7.5); 7.782 (5.2); 7.762 (5.6); 7.669 (3.7); 7.664 (5.1); 7.659 (3.6); 7.649 (4.1); 7.644 (5.4); 7.639 (3.7); 7.520 (2.8); 7.391 (5.0); 7.379 (5.1); 7.371 (4.7); 7.359 (4.5); 7.335 (2.1); 7.319 (4.3); 7.314 (4.0); 7.303 (2.9); 7.298 (8.9); 7.293 (2.9); 7.282 (5.0); 7.277 (6.4); 7.261 (510.7); 7.230 (5.5); 7.218 (5.3); 7.212 (4.9); 7.210 (5.7); 7.200 (4.7); 7.162 (2.2); 7.146 (4.6); 7.141 (4.5); 7.130 (2.8); 7.125 (9.3); 7.120 (3.0); 7.109 (4.4); 7.104 (5.1); 7.088 (2.5); 6.997 (2.8); 6.965 (9.9); 6.943 (16.0); 6.922 (8.7); 6.765 (7.9); 6.743 (13.2); 6.721 (7.0); 5.298 (4.8); 4.335 (8.9); 4.310 (9.8); 4.265 (10.6); 4.237 (12.4); 3.937 (2.1); 3.926 (2.5); 3.908 (3.9); 3.899 (4.0); 3.871 (3.2); 3.863 (2.1); 3.847 (3.3); 3.836 (3.3); 3.821 (1.9); 3.809 (1.7); 3.741 (2.7); 3.730 (3.2); 3.726 (3.3); 3.714 (5.7); 3.709 (4.7); 3.703 (4.0); 3.699 (3.8); 3.688 (3.4); 3.602 (2.9); 3.591 (2.3); 3.580 (2.9); 3.576 (3.1); 3.564 (5.3); 3.553 (3.8); 3.549 (3.8); 3.538 (3.0); 3.493 (2.9); 3.480 (3.2); 3.470 (3.4); 3.466 (2.9); 3.458 (3.5); 3.453 (2.9); 3.443 (2.6); 3.430 (2.6); 3.398 (2.8); 3.386 (3.0); 3.376 (3.4); 3.371 (2.9); 3.363 (3.4); 3.359 (2.8); 3.349 (2.4); 3.336 (2.1); 2.926 (0.7); 2.907 (0.5); 2.578 (1.3); 2.568 (1.4); 2.563 (1.4); 2.554 (2.0); 2.544 (2.7); 2.533 (2.2); 2.529 (2.7); 2.520 (2.6); 2.511 (1.9); 2.505 (1.7); 2.496 (1.6); 2.346 (1.3); 2.334 (1.8); 2.322 (1.6); 2.318 (1.7); 2.304 (2.4); 2.283 (1.3); 2.271 (1.3); 2.259 (0.9); 2.086 (1.6); 2.051 (2.5); 2.037 (1.7); 2.024 (1.9); 1.857 (1.6); 1.842 (2.1); 1.830 (2.3); 1.822 (3.0); 1.808 (2.9); 1.798 (1.8); 1.789 (1.8); 1.774 (1.4); 1.620 (3.9); 1.359 (0.5); 1.284 (0.7); 1.255 (2.8); 0.940 (0.5); 0.146 (0.5); 0.069 (6.4); 0.008 (5.8); 0.000 (181.4); −0.009 (5.2); −0.150 (0.5)

[0431]

Example 1:1H-NMR (400.0 MHz, CDCl3): δ=8.190 (8.6); 8.183 (8.7); 7.875 (4.3); 7.868 (4.1); 7.856 (4.7); 7.853 (5.2); 7.850 (4.8); 7.847 (4.8); 7.835 (4.5); 7.829 (4.3); 7.519 (1.4); 7.340 (2.4); 7.324 (4.9); 7.319 (4.1); 7.308 (2.9); 7.303 (10.0); 7.298 (3.2); 7.287 (4.2); 7.282 (5.8); 7.266 (5.6); 7.260 (243.5); 7.147 (0.6); 7.020 (6.4); 7.012 (6.4); 6.998 (6.3); 6.991 (6.1); 6.969 (4.7); 6.965 (9.9); 6.948 (4.9); 6.943 (16.0); 6.939 (5.2); 6.922 (8.5); 6.918 (4.2); 4.356 (11.4); 4.331 (12.5); 3.857 (2.0); 3.846 (2.2); 3.831 (3.5); 3.820 (3.5); 3.805 (2.0); 3.794 (1.9); 3.621 (2.3); 3.610 (2.9); 3.607 (3.0); 3.595 (5.0); 3.583 (3.7); 3.580 (3.8); 3.568 (3.0); 3.416 (2.5); 3.404 (2.8); 3.393 (3.1); 3.381 (3.1); 3.366 (2.2); 3.354 (2.0); 2.104 (0.9); 2.092 (1.7); 2.080 (1.4); 2.077 (1.5); 2.073 (1.3); 2.069 (2.1); 2.065 (2.3); 2.061 (2.3); 2.058 (2.7); 2.054 (2.1); 2.050 (1.3); 2.046 (1.9); 2.042 (1.8); 2.031 (2.1); 2.019 (1.1); 1.878 (1.6); 1.865 (2.0); 1.853 (2.1); 1.843 (3.2); 1.829 (3.0); 1.820 (1.5); 1.808 (1.5); 1.795 (1.1); 1.538 (2.4); 1.333 (1.0); 1.284 (1.4); 1.255 (1.8); 0.008 (2.6); 0.000 (85.5); −0.009 (2.4)

[0432]

Example 462:1H-NMR (400.0 MHz, CDCl3): δ=8.436 (11.9); 8.429 (11.6); 8.403 (7.7); 8.397 (7.4); 8.277 (7.1); 8.273 (10.2); 8.227 (6.6); 7.520 (0.6); 7.410 (2.4); 7.405 (3.2); 7.399 (2.2); 7.389 (2.4); 7.383 (3.1); 7.377 (2.1); 7.262 (98.6); 7.221 (4.0); 7.215 (5.2); 7.210 (4.0); 7.199 (4.1); 7.193 (5.2); 7.188 (3.7); 7.178 (3.5); 7.170 (3.9); 7.164 (3.8); 7.156 (5.9); 7.148 (3.8); 7.142 (3.5); 7.134 (3.4); 7.113 (0.8); 7.018 (1.8); 7.006 (3.2); 6.995 (5.6); 6.987 (4.2); 6.983 (6.8); 6.976 (5.0); 6.972 (6.0); 6.965 (6.3); 6.961 (5.4); 6.957 (4.8); 6.954 (5.5); 6.951 (3.7); 6.947 (4.2); 6.942 (6.3); 6.935 (3.7); 6.930 (6.0); 6.925 (3.6); 6.918 (6.8); 6.912 (2.8); 6.907 (6.4); 6.895 (3.1); 6.884 (2.7); 6.870 (2.6); 6.863 (2.4); 6.856 (2.6); 6.849 (3.8); 6.841 (2.3); 6.835 (2.4); 6.828 (1.9); 5.298 (16.0); 4.408 (8.5); 4.391 (8.8); 4.368 (0.7); 4.364 (0.6); 4.355 (0.6); 4.351 (0.6); 4.196 (5.2); 4.175 (5.5); 3.771 (3.7); 3.758 (8.4); 3.745 (7.5); 3.731 (7.6); 3.719 (6.2); 3.709 (2.7); 3.704 (2.6); 3.693 (3.5); 3.681 (3.7); 3.677 (3.8); 3.667 (3.5); 3.657 (2.0); 3.648 (2.7); 3.641 (1.9); 3.628 (1.7); 3.619 (1.6); 3.560 (3.2); 3.547 (3.5); 3.540 (3.7); 3.533 (3.2); 3.527 (3.7); 3.520 (2.9); 3.513 (2.9); 3.500 (2.6); 3.434 (2.1); 3.422 (2.3); 3.410 (2.6); 3.407 (2.2); 3.398 (2.5); 3.395 (2.2); 3.384 (2.0); 3.372 (1.8); 2.365 (0.8); 2.356 (1.0); 2.350 (1.0); 2.341 (1.5); 2.330 (1.7); 2.320 (1.5); 2.315 (1.7); 2.306 (2.2); 2.297 (1.4); 2.292 (1.3); 2.282 (1.1); 2.204 (1.0); 2.195 (1.6); 2.179 (1.2); 2.165 (2.1); 2.157 (1.7); 2.150 (1.7); 2.129 (3.6); 2.114 (5.8); 2.109 (3.9); 2.100 (6.5); 2.094 (4.8); 2.079 (5.5); 2.065 (2.8); 2.056 (1.2); 2.042 (1.3); 2.031 (0.8); 2.004 (0.6); 1.602 (2.7); 0.008 (2.5); 0.000 (39.1); −0.009 (1.5)

[0433]

Example 1835:1H-NMR (400.0 MHz, CDCl3): δ=8.443 (15.9); 8.436 (16.0); 8.404 (11.2); 8.397 (11.2); 8.267 (7.9); 8.263 (12.4); 8.259 (7.7); 8.224 (5.5); 8.220 (8.8); 8.216 (5.4); 7.520 (1.8); 7.410 (2.9); 7.404 (4.1); 7.398 (2.9); 7.388 (3.0); 7.382 (4.1); 7.376 (2.8); 7.290 (0.6); 7.287 (0.5); 7.285 (0.6); 7.282 (0.6); 7.280 (0.6); 7.279 (0.7); 7.2783 (0.7); 7.2775 (0.7); 7.277 (0.9); 7.276 (1.0); 7.275 (1.1); 7.2743 (1.2); 7.2735 (1.3); 7.273 (1.4); 7.272 (1.5); 7.271 (1.8); 7.2703 (2.0); 7.2695 (2.3); 7.269 (2.6); 7.268 (2.8); 7.267 (3.4); 7.2663 (4.1); 7.2655 (5.1); 7.265 (6.5); 7.261 (316.4); 7.256 (3.6); 7.255 (2.6); 7.254 (2.7); 7.2533 (1.5); 7.2525 (1.1); 7.252 (1.7); 7.251 (0.9); 7.250 (0.7); 7.2493 (0.8); 7.2485 (0.8); 7.248 (0.8); 7.247 (0.8); 7.246 (0.8); 7.243 (1.8); 7.239 (2.5); 7.233 (1.8); 7.225 (5.0); 7.220 (4.0); 7.216 (3.1); 7.206 (8.0); 7.201 (7.9); 7.195 (4.0); 7.184 (4.1); 7.178 (7.3); 7.173 (4.1); 7.168 (2.6); 7.165 (2.2); 7.160 (5.7); 7.158 (5.5); 7.147 (9.0); 7.144 (5.4); 7.140 (9.7); 7.129 (5.2); 7.124 (7.0); 7.118 (5.0); 7.112 (1.9); 7.109 (2.2); 7.105 (4.2); 7.100 (4.0); 7.096 (3.3); 7.092 (3.7); 7.088 (1.7); 7.085 (2.1); 7.078 (3.2); 7.073 (4.0); 7.067 (2.9); 7.064 (2.8); 7.061 (2.5); 7.055 (3.1); 7.049 (5.7); 7.046 (3.2); 7.042 (3.2); 7.032 (3.0); 7.030 (3.2); 7.025 (1.4); 7.021 (1.5); 7.011 (1.2); 7.009 (1.4); 6.997 (1.9); 6.931 (1.7); 6.927 (2.9); 6.923 (1.8); 6.916 (1.9); 6.912 (3.3); 6.908 (3.6); 6.898 (1.3); 6.893 (2.0); 6.889 (1.2); 5.299 (6.1); 4.418 (10.5); 4.401 (11.1); 4.201 (7.1); 4.179 (7.8); 3.824 (2.4); 3.807 (4.7); 3.802 (3.0); 3.791 (2.8); 3.786 (4.9); 3.769 (3.2); 3.759 (2.1); 3.744 (4.0); 3.734 (4.4); 3.723 (4.2); 3.714 (4.6); 3.706 (3.6); 3.694 (3.4); 3.685 (3.4); 3.534 (2.2); 3.422 (1.2); 3.410 (1.6); 3.397 (1.9); 3.386 (1.5); 3.373 (1.1); 2.378 (0.9); 2.369 (1.0); 2.363 (1.0); 2.354 (1.5); 2.343 (2.0); 2.334 (1.7); 2.329 (2.0); 2.319 (2.5); 2.310 (1.7); 2.305 (1.6); 2.295 (1.4); 2.241 (1.0); 2.231 (1.8); 2.218 (1.1); 2.203 (1.9); 2.196 (1.7); 2.181 (1.3); 2.167 (1.7); 2.160 (3.0); 2.146 (4.5); 2.139 (5.7); 2.126 (6.0); 2.116 (4.9); 2.103 (2.7); 2.094 (0.6); 2.080 (0.7); 1.568 (10.7); 1.427 (3.9); 1.333 (2.6); 0.008 (3.8); 0.0063 (1.2); 0.0055 (1.3); 0.005 (1.6); 0.000 (122.7); −0.005 (2.1); −0.006 (1.6); −0.007 (1.4); −0.009 (3.7)

[0434]

Example 543:1H-NMR (400.0 MHz, CDCl3): δ=8.573 (10.8); 8.569 (11.2); 8.561 (11.2); 8.557 (10.8); 8.535 (0.5); 8.531 (0.6); 8.523 (0.6); 8.519 (0.5); 8.449 (12.5); 8.444 (12.2); 8.405 (0.5); 8.399 (0.6); 7.520 (2.4); 7.493 (4.7); 7.488 (6.3); 7.483 (4.6); 7.473 (5.7); 7.468 (7.4); 7.463 (5.2); 7.345 (0.7); 7.293 (1.0); 7.261 (436.3); 7.255 (2.7); 7.252 (8.1); 7.250 (7.7); 7.244 (6.5); 7.242 (6.4); 7.232 (6.2); 7.230 (5.8); 7.159 (4.4); 7.151 (4.9); 7.145 (4.7); 7.137 (8.4); 7.129 (4.9); 7.123 (4.6); 7.116 (4.6); 6.997 (2.6); 6.987 (2.5); 6.979 (2.5); 6.977 (3.1); 6.969 (4.6); 6.964 (5.6); 6.961 (2.9); 6.957 (6.0); 6.954 (5.6); 6.951 (3.3); 6.946 (9.2); 6.939 (5.9); 6.936 (5.5); 6.928 (10.3); 6.916 (7.0); 6.904 (9.7); 6.893 (9.4); 6.882 (3.5); 6.870 (3.2); 5.299 (2.3); 4.334 (15.1); 4.316 (16.0); 4.148 (0.6); 4.127 (0.7); 3.760 (2.2); 3.743 (8.0); 3.730 (10.1); 3.716 (10.4); 3.703 (11.2); 3.690 (5.2); 3.679 (0.5); 3.536 (4.5); 3.522 (4.6); 3.516 (5.0); 3.509 (4.1); 3.502 (5.1); 3.496 (3.7); 3.489 (3.9); 3.475 (3.7); 2.148 (0.7); 2.133 (1.3); 2.112 (3.8); 2.098 (8.5); 2.092 (4.3); 2.084 (8.6); 2.078 (6.4); 2.072 (5.2); 2.062 (7.3); 2.049 (3.3); 2.038 (1.0); 2.027 (1.2); 2.013 (0.5); 1.576 (7.4); 0.008 (5.0); 0.0063 (1.8); 0.0055 (2.1); 0.000 (145.6); −0.005 (1.2); −0.006 (1.0); −0.007 (0.9); −0.009 (3.9)

[0435]

Example 461:1H-NMR (400.0 MHz, CDCl3): δ=8.192 (7.3); 8.185 (7.4); 8.143 (4.9); 8.137 (5.0); 7.518 (2.7); 7.512 (2.4); 7.498 (6.5); 7.491 (6.7); 7.471 (8.2); 7.470 (8.4); 7.451 (3.3); 7.449 (3.1); 7.437 (6.9); 7.417 (9.8); 7.328 (6.8); 7.321 (6.7); 7.307 (4.6); 7.301 (4.5); 7.261 (174.5); 7.172 (2.5); 7.165 (2.8); 7.158 (2.7); 7.151 (4.7); 7.143 (2.7); 7.137 (2.6); 7.129 (2.6); 7.014 (1.2); 7.002 (2.6); 6.997 (1.4); 6.994 (1.5); 6.991 (4.6); 6.984 (2.7); 6.979 (6.5); 6.972 (3.7); 6.968 (4.8); 6.961 (6.1); 6.955 (5.8); 6.951 (4.8); 6.948 (5.0); 6.944 (5.4); 6.937 (6.1); 6.934 (3.5); 6.926 (6.8); 6.922 (2.2); 6.914 (6.2); 6.903 (2.3); 6.891 (1.7); 6.855 (1.9); 6.848 (1.8); 6.841 (2.0); 6.834 (3.4); 6.826 (1.9); 6.820 (2.0); 6.813 (1.6); 5.299 (16.0); 4.334 (9.0); 4.318 (9.5); 4.127 (6.5); 4.105 (7.0); 3.749 (2.6); 3.730 (4.2); 3.710 (4.1); 3.692 (2.4); 3.676 (1.4); 3.653 (1.3); 3.643 (1.3); 3.631 (1.2); 3.623 (2.1); 3.615 (1.3); 3.603 (1.2); 3.593 (1.1); 3.526 (1.7); 3.396 (1.3); 2.362 (0.8); 2.352 (0.9); 2.347 (0.9); 2.338 (1.4); 2.327 (1.5); 2.318 (1.3); 2.312 (1.5); 2.303 (2.1); 2.294 (1.2); 2.289 (1.1); 2.279 (1.0); 2.181 (0.7); 2.170 (1.3); 2.161 (0.8); 2.158 (0.9); 2.153 (1.1); 2.139 (1.8); 2.133 (1.6); 2.124 (1.1); 2.118 (2.6); 2.104 (3.8); 2.098 (3.8); 2.085 (4.8); 2.075 (2.9); 2.069 (2.3); 2.064 (3.4); 2.051 (2.0); 2.040 (0.6); 2.029 (0.8); 1.570 (8.4); 1.423 (2.5); 1.338 (1.5); 0.069 (0.6); 0.008 (1.9); 0.000 (64.2); −0.009 (1.8)

[0436]

Example 1875:1H-NMR (400.0 MHz, CDCl3): δ=8.355 (10.2); 8.349 (10.1); 8.083 (10.3); 8.077 (10.3); 7.721 (7.6); 7.714 (7.4); 7.700 (8.3); 7.693 (8.3); 7.626 (7.4); 7.619 (7.3); 7.605 (8.4); 7.598 (8.3); 7.519 (5.6); 7.415 (11.3); 7.395 (9.8); 7.394 (9.7); 7.360 (1.2); 7.310 (1.5); 7.300 (1.2); 7.293 (13.7); 7.272 (14.5); 7.260 (1016.6); 7.229 (1.4); 7.225 (0.9); 7.012 (6.0); 7.005 (15.5); 6.996 (6.3); 6.984 (15.3); 6.977 (5.7); 6.847 (5.3); 6.841 (16.0); 6.820 (15.6); 6.813 (5.1); 4.299 (9.9); 4.274 (10.9); 4.222 (10.6); 4.194 (12.6); 3.896 (2.2); 3.886 (2.3); 3.868 (3.7); 3.858 (3.8); 3.840 (1.9); 3.830 (1.8); 3.817 (2.0); 3.805 (2.1); 3.791 (3.1); 3.779 (3.4); 3.750 (3.0); 3.734 (3.0); 3.722 (2.9); 3.708 (2.0); 3.637 (1.4); 3.624 (2.5); 3.611 (2.9); 3.597 (3.2); 3.585 (1.8); 3.436 (2.5); 3.412 (2.5); 3.389 (2.4); 2.550 (1.4); 2.536 (1.5); 2.526 (2.6); 2.516 (2.8); 2.502 (2.8); 2.491 (3.2); 2.482 (1.9); 2.468 (1.5); 2.268 (2.1); 2.240 (2.4); 2.204 (1.5); 2.057 (1.3); 2.030 (2.1); 2.022 (2.7); 2.007 (1.7); 1.995 (1.9); 1.874 (1.3); 1.861 (2.1); 1.849 (2.2); 1.839 (3.0); 1.826 (2.7); 1.815 (1.6); 1.804 (1.7); 1.791 (1.0); 1.538 (43.6); 1.303 (2.0); 1.227 (1.9); 0.331 (0.6); 0.157 (0.9); 0.146 (1.1); 0.008 (11.7); 0.000 (373.7); −0.009 (11.1); −0.031 (0.9); −0.150 (1.3)

[0437]

Example 1962:1H-NMR (400.0 MHz, CDCl3): δ=8.153 (14.5); 8.146 (14.2); 8.112 (10.6); 8.105 (10.5); 7.519 (9.0); 7.487 (5.3); 7.481 (5.1); 7.466 (12.1); 7.460 (12.1); 7.435 (20.5); 7.434 (20.2); 7.420 (8.7); 7.415 (15.1); 7.412 (18.5); 7.402 (5.3); 7.397 (5.8); 7.390 (17.7); 7.309 (3.7); 7.304 (3.4); 7.295 (3.8); 7.290 (7.6); 7.285 (6.9); 7.281 (13.4); 7.274 (17.4); 7.270 (17.0); 7.268 (15.2); 7.267 (15.5); 7.260 (1631.1); 7.254 (24.8); 7.253 (21.9); 7.251 (9.2); 7.250 (8.8); 7.249 (8.0); 7.248 (7.0); 7.247 (8.2); 7.245 (5.0); 7.244 (7.0); 7.2404 (2.2); 7.2396 (2.1); 7.236 (3.8); 7.233 (5.0); 7.227 (5.4); 7.222 (3.2); 7.213 (3.6); 7.209 (9.1); 7.206 (8.5); 7.190 (11.2); 7.187 (11.5); 7.171 (4.4); 7.168 (4.1); 7.109 (2.0); 7.095 (6.6); 7.089 (9.4); 7.083 (12.9); 7.082 (12.6); 7.072 (8.1); 7.070 (8.3); 7.050 (1.9); 7.028 (5.1); 7.005 (4.6); 7.000 (6.6); 6.996 (9.8); 6.980 (4.5); 6.974 (6.4); 6.971 (6.3); 6.954 (5.5); 6.948 (7.4); 6.945 (6.4); 6.928 (5.2); 6.925 (5.5); 5.299 (3.8); 4.320 (15.3); 4.303 (16.0); 4.142 (12.0); 4.120 (13.1); 3.762 (2.8); 3.744 (9.8); 3.731 (8.8); 3.725 (7.2); 3.717 (8.9); 3.704 (10.9); 3.691 (6.1); 3.682 (3.5); 3.678 (3.5); 3.666 (5.8); 3.656 (4.1); 3.651 (4.2); 3.646 (3.3); 3.640 (4.2); 3.623 (2.8); 3.617 (3.7); 3.608 (3.2); 3.595 (2.8); 3.585 (2.6); 3.543 (4.1); 3.526 (7.2); 3.516 (3.8); 3.509 (4.5); 3.499 (5.9); 3.482 (3.5); 3.427 (3.2); 3.415 (3.6); 3.404 (3.8); 3.401 (3.3); 3.392 (3.9); 3.377 (3.0); 3.365 (2.9); 2.380 (1.2); 2.371 (1.7); 2.356 (2.2); 2.346 (2.8); 2.336 (2.5); 2.331 (3.2); 2.323 (3.2); 2.313 (2.2); 2.308 (2.3); 2.298 (1.9); 2.241 (1.4); 2.230 (2.5); 2.202 (2.7); 2.167 (1.8); 2.143 (6.4); 2.126 (11.0); 2.112 (10.3); 2.095 (5.9); 2.005 (1.2); 1.525 (10.9); 0.331 (1.2); 0.157 (2.0); 0.146 (1.9); 0.032 (1.1); 0.008 (19.4); 0.006 (7.3); 0.005 (8.7); 0.000 (635.3); −0.009 (16.8); −0.150 (2.0)

[0438]

Example 15 (erythro):1H-NMR (400.0 MHz, CDCl3): δ=8.110 (8.3); 8.107 (9.0); 8.104 (9.8); 8.101 (9.2); 8.021 (8.8); 8.015 (8.2); 8.001 (8.7); 7.995 (8.1); 7.934 (2.0); 7.928 (2.2); 7.915 (2.2); 7.909 (2.5); 7.806 (2.6); 7.518 (7.9); 7.355 (2.2); 7.339 (4.7); 7.335 (4.2); 7.323 (3.1); 7.318 (9.4); 7.313 (3.5); 7.309 (2.0); 7.303 (4.2); 7.297 (5.8); 7.292 (2.3); 7.281 (4.9); 7.260 (1475.3); 7.224 (1.5); 7.210 (1.9); 7.191 (2.7); 7.175 (1.3); 7.169 (1.8); 6.996 (8.3); 6.976 (9.7); 6.955 (16.0); 6.933 (8.5); 6.827 (2.4); 6.805 (4.3); 6.783 (2.1); 4.359 (11.5); 4.334 (12.9); 4.264 (3.5); 4.236 (3.8); 4.130 (2.0); 4.113 (1.8); 4.032 (1.4); 3.914 (1.0); 3.887 (1.2); 3.853 (2.3); 3.841 (2.3); 3.827 (3.6); 3.816 (3.4); 3.802 (2.1); 3.789 (2.0); 3.738 (1.3); 3.727 (1.4); 3.713 (1.1); 3.658 (1.4); 3.647 (2.8); 3.632 (4.3); 3.620 (4.7); 3.606 (3.8); 3.594 (1.7); 3.437 (2.9); 3.425 (3.1); 3.414 (3.4); 3.399 (2.6); 3.387 (2.5); 3.375 (1.3); 2.524 (1.1); 2.107 (1.7); 2.072 (2.8); 2.044 (9.4); 1.903 (1.4); 1.889 (2.3); 1.879 (2.2); 1.868 (3.2); 1.855 (2.7); 1.844 (1.4); 1.834 (1.6); 1.820 (1.2); 1.535 (512.6); 1.319 (2.0); 1.305 (3.0); 1.293 (2.2); 1.276 (3.7); 1.268 (8.1); 1.256 (11.7); 1.244 (6.3); 1.241 (3.5); 0.899 (1.5); 0.882 (4.7); 0.864 (1.7); 0.146 (1.7); 0.008 (17.0); 0.000 (580.3); −0.009 (17.1); −0.150 (1.6)

[0439]

Example 1964:1H-NMR (400.0 MHz, CDCl3): δ=8.515 (15.7); 8.509 (16.0); 8.466 (10.8); 8.461 (10.9); 8.277 (13.9); 8.272 (14.1); 8.245 (9.2); 8.240 (9.5); 7.623 (5.7); 7.617 (10.6); 7.612 (5.6); 7.519 (3.3); 7.442 (3.3); 7.438 (3.6); 7.424 (6.5); 7.419 (7.0); 7.406 (10.5); 7.401 (17.0); 7.396 (7.2); 7.360 (0.6); 7.320 (2.4); 7.315 (2.5); 7.307 (2.9); 7.302 (5.3); 7.299 (3.8); 7.297 (4.1); 7.295 (3.6); 7.288 (5.0); 7.286 (4.0); 7.283 (4.8); 7.281 (6.3); 7.276 (6.4); 7.271 (4.5); 7.268 (8.4); 7.260 (614.4); 7.252 (2.9); 7.251 (3.5); 7.249 (2.3); 7.248 (2.0); 7.246 (2.9); 7.244 (1.7); 7.242 (2.7); 7.240 (3.2); 7.238 (3.4); 7.236 (3.0); 7.233 (3.1); 7.227 (2.5); 7.226 (3.6); 7.223 (6.8); 7.219 (8.9); 7.209 (1.8); 7.204 (9.2); 7.201 (9.5); 7.185 (4.1); 7.182 (4.0); 7.170 (0.6); 7.148 (0.6); 7.135 (1.4); 7.130 (1.7); 7.116 (4.2); 7.111 (3.9); 7.098 (5.4); 7.093 (8.5); 7.079 (5.4); 7.076 (6.0); 7.060 (2.1); 7.057 (2.2); 7.042 (3.7); 7.039 (3.3); 7.021 (3.1); 7.018 (3.1); 7.014 (3.6); 6.996 (4.3); 6.991 (2.8); 6.975 (4.7); 6.972 (4.8); 6.955 (4.5); 6.951 (4.9); 6.949 (5.4); 6.946 (5.0); 6.929 (4.3); 6.925 (4.2); 4.350 (12.3); 4.333 (13.0); 4.170 (8.3); 4.148 (9.0); 3.782 (0.6); 3.770 (2.3); 3.751 (6.2); 3.734 (7.2); 3.722 (3.4); 3.714 (3.9); 3.710 (3.8); 3.697 (2.7); 3.672 (2.2); 3.662 (3.5); 3.653 (3.3); 3.641 (2.6); 3.634 (3.0); 3.624 (2.3); 3.613 (2.1); 3.603 (2.0); 3.558 (1.5); 3.553 (1.5); 3.536 (2.7); 3.510 (2.3); 3.493 (1.3); 3.407 (1.7); 2.371 (0.9); 2.361 (1.0); 2.356 (1.0); 2.346 (1.3); 2.336 (2.1); 2.326 (1.8); 2.321 (2.1); 2.313 (2.2); 2.304 (1.8); 2.298 (1.8); 2.288 (1.6); 2.260 (1.1); 2.250 (2.1); 2.237 (1.4); 2.222 (2.1); 2.212 (1.5); 2.201 (0.9); 2.187 (1.2); 2.174 (0.7); 2.151 (5.1); 2.137 (7.5); 2.133 (8.5); 2.119 (8.7); 2.102 (4.9); 1.557 (5.2); 1.352 (2.4); 1.262 (1.8); 0.146 (0.7); 0.008 (6.9); 0.000 (249.9); −0.009 (7.0); −0.033 (0.6); −0.150 (0.8)

[0440]

Example 14 (erythro):1H-NMR (400.0 MHz, CDCl3): δ=8.068 (8.4); 8.065 (9.4); 8.063 (9.9); 8.060 (8.8); 7.878 (8.7); 7.872 (8.3); 7.858 (8.9); 7.852 (8.3); 7.519 (1.2); 7.355 (2.3); 7.339 (4.6); 7.334 (3.9); 7.323 (2.7); 7.318 (9.4); 7.313 (3.0); 7.302 (3.9); 7.297 (5.3); 7.281 (2.9); 7.275 (0.7); 7.273 (0.9); 7.270 (1.3); 7.269 (1.6); 7.260 (201.5); 6.996 (1.2); 6.979 (4.6); 6.975 (9.8); 6.958 (5.0); 6.953 (16.0); 6.949 (5.2); 6.932 (8.6); 6.928 (4.3); 5.298 (0.7); 4.367 (11.6); 4.342 (12.8); 3.934 (0.9); 3.857 (2.0); 3.845 (2.1); 3.830 (3.5); 3.820 (3.5); 3.805 (1.9); 3.794 (1.9); 3.650 (2.2); 3.636 (3.1); 3.624 (4.8); 3.609 (3.9); 3.597 (2.9); 3.439 (2.4); 3.427 (2.7); 3.416 (3.1); 3.405 (3.0); 3.390 (2.1); 3.378 (2.0); 2.118 (0.9); 2.110 (1.1); 2.106 (1.7); 2.103 (1.1); 2.094 (1.4); 2.091 (1.4); 2.087 (1.2); 2.083 (2.2); 2.080 (2.4); 2.075 (2.2); 2.072 (2.9); 2.068 (2.2); 2.064 (1.3); 2.060 (1.8); 2.057 (1.8); 2.048 (1.4); 2.045 (2.3); 2.042 (1.4); 2.033 (1.1); 1.901 (1.5); 1.888 (2.3); 1.877 (2.1); 1.866 (3.3); 1.853 (3.0); 1.842 (1.6); 1.831 (1.6); 1.818 (1.0); 1.549 (2.2); 1.333 (1.1); 1.284 (1.3); 1.256 (1.2); 0.008 (2.2); 0.000 (71.5); −0.009 (2.1)

[0441]

Example 6:1H-NMR (400.0 MHz, CDCl3): δ=8.694 (9.5); 8.689 (9.6); 8.633 (0.6); 8.629 (0.7); 8.621 (0.7); 8.617 (0.7); 8.567 (0.6); 8.562 (0.7); 8.520 (10.9); 8.515 (11.3); 8.508 (9.4); 8.503 (9.3); 8.485 (0.5); 8.481 (0.6); 8.473 (0.6); 8.469 (0.5); 8.207 (8.4); 8.202 (8.5); 7.889 (5.4); 7.888 (5.4); 7.884 (10.2); 7.878 (5.1); 7.787 (5.7); 7.782 (10.5); 7.777 (5.3); 7.521 (1.1); 7.361 (0.6); 7.349 (1.7); 7.333 (2.8); 7.328 (2.6); 7.317 (1.7); 7.312 (5.4); 7.307 (2.2); 7.302 (0.6); 7.296 (2.4); 7.291 (3.3); 7.286 (1.1); 7.284 (0.6); 7.2834 (0.6); 7.2825 (0.6); 7.282 (0.7); 7.281 (0.8); 7.280 (0.8); 7.2794 (0.8); 7.2786 (0.8); 7.278 (0.9); 7.275 (2.2); 7.273 (1.3); 7.272 (1.3); 7.2714 (1.4); 7.2706 (1.6); 7.270 (1.7); 7.269 (2.0); 7.268 (2.2); 7.2674 (2.6); 7.2666 (3.2); 7.266 (4.1); 7.262 (197.8); 7.257 (2.2); 7.256 (1.5); 7.255 (1.1); 7.2544 (0.9); 7.2535 (1.0); 7.253 (0.9); 7.252 (0.7); 7.2512 (0.7); 7.2505 (0.6); 7.211 (0.6); 7.205 (1.5); 7.189 (3.2); 7.184 (2.9); 7.173 (1.8); 7.168 (6.5); 7.163 (2.0); 7.152 (2.9); 7.147 (3.5); 7.140 (0.6); 7.131 (1.7); 6.998 (1.2); 6.977 (2.7); 6.973 (5.8); 6.956 (2.9); 6.951 (9.3); 6.947 (3.1); 6.935 (1.0); 6.930 (5.0); 6.926 (2.6); 6.914 (1.1); 6.892 (0.5); 6.807 (5.6); 6.786 (9.3); 6.770 (1.0); 6.764 (5.0); 6.749 (1.1); 6.728 (0.5); 5.299 (16.0); 4.383 (0.7); 4.360 (0.9); 4.328 (7.0); 4.303 (7.7); 4.243 (8.0); 4.215 (9.4); 4.200 (0.9); 3.922 (1.4); 3.912 (1.4); 3.893 (2.5); 3.884 (2.6); 3.864 (2.1); 3.853 (1.8); 3.837 (2.0); 3.825 (2.0); 3.811 (1.1); 3.800 (1.1); 3.748 (0.9); 3.735 (1.5); 3.722 (2.0); 3.709 (1.8); 3.696 (1.2); 3.616 (7.1); 3.596 (1.7); 3.583 (1.7); 3.570 (1.0); 3.552 (8.2); 3.486 (0.9); 3.473 (1.0); 3.462 (1.5); 3.450 (1.5); 3.437 (0.9); 3.424 (1.5); 3.411 (1.0); 3.400 (1.3); 3.388 (1.3); 3.361 (0.6); 2.557 (0.9); 2.547 (0.9); 2.542 (1.0); 2.533 (1.4); 2.523 (1.9); 2.512 (1.4); 2.508 (1.9); 2.498 (1.9); 2.489 (1.3); 2.484 (1.2); 2.474 (1.1); 2.336 (0.8); 2.332 (0.6); 2.324 (1.3); 2.312 (1.0); 2.308 (1.0); 2.295 (1.5); 2.285 (1.2); 2.278 (0.8); 2.273 (0.7); 2.261 (0.9); 2.250 (0.6); 2.169 (1.2); 2.112 (0.5); 2.100 (0.9); 2.089 (0.8); 2.085 (0.8); 2.082 (0.7); 2.078 (1.1); 2.074 (1.3); 2.070 (1.2); 2.066 (1.5); 2.062 (1.1); 2.058 (0.8); 2.054 (1.1); 2.051 (1.0); 2.039 (1.2); 2.027 (0.6); 1.878 (0.9); 1.865 (1.2); 1.852 (1.1); 1.844 (1.8); 1.829 (1.6); 1.821 (0.8); 1.809 (0.9); 1.795 (0.6); 1.593 (4.4); 1.413 (1.4); 1.346 (1.2); 0.008 (1.9); 0.000 (69.3); −0.007 (0.5); −0.009 (2.0)

[0442]

Example 4:1H-NMR (400.0 MHz, CDCl3): δ=8.500 (11.0); 8.494 (11.0); 8.425 (6.0); 8.420 (9.1); 8.417 (5.8); 8.328 (13.1); 8.322 (13.2); 8.124 (9.7); 7.521 (0.8); 7.507 (3.4); 7.502 (4.0); 7.501 (4.0); 7.495 (3.2); 7.485 (3.3); 7.480 (4.1); 7.479 (4.0); 7.474 (3.1); 7.400 (3.6); 7.394 (4.6); 7.389 (3.5); 7.378 (3.7); 7.373 (4.5); 7.367 (3.4); 7.345 (1.8); 7.329 (3.7); 7.324 (3.1); 7.313 (2.1); 7.308 (7.5); 7.303 (2.3); 7.292 (2.9); 7.287 (4.2); 7.271 (2.6); 7.262 (144.6); 7.2564 (0.8); 7.2556 (0.6); 7.193 (2.1); 7.176 (4.4); 7.171 (4.0); 7.160 (2.5); 7.155 (9.0); 7.151 (2.8); 7.139 (4.0); 7.134 (4.9); 7.118 (2.4); 6.998 (0.8); 6.973 (3.4); 6.969 (7.2); 6.952 (3.5); 6.947 (11.8); 6.942 (3.8); 6.926 (6.3); 6.921 (3.2); 6.794 (7.3); 6.773 (12.1); 6.751 (6.4); 5.298 (16.0); 4.392 (6.4); 4.367 (7.0); 4.312 (6.7); 4.284 (7.7); 3.941 (1.7); 3.931 (1.8); 3.912 (3.3); 3.902 (3.3); 3.883 (2.8); 3.874 (2.4); 3.856 (2.5); 3.845 (2.4); 3.831 (1.4); 3.819 (1.4); 3.745 (2.4); 3.734 (2.8); 3.730 (2.9); 3.718 (4.7); 3.707 (3.5); 3.703 (3.4); 3.692 (3.0); 3.620 (2.0); 3.609 (2.4); 3.605 (2.5); 3.593 (4.5); 3.581 (3.1); 3.578 (3.2); 3.567 (2.6); 3.486 (2.6); 3.474 (2.9); 3.463 (3.0); 3.459 (2.5); 3.451 (3.0); 3.447 (2.6); 3.436 (2.4); 3.424 (2.4); 3.418 (2.3); 3.406 (2.4); 3.395 (2.6); 3.391 (2.1); 3.383 (2.6); 3.379 (2.1); 3.368 (2.0); 3.356 (1.8); 2.565 (1.2); 2.555 (1.3); 2.550 (1.3); 2.541 (1.8); 2.531 (2.4); 2.520 (1.8); 2.516 (2.4); 2.506 (2.4); 2.497 (1.7); 2.492 (1.5); 2.482 (1.4); 2.342 (0.6); 2.338 (1.0); 2.335 (0.7); 2.326 (1.6); 2.319 (0.7); 2.315 (1.3); 2.310 (1.3); 2.303 (1.5); 2.298 (1.9); 2.287 (1.4); 2.280 (1.0); 2.276 (1.0); 2.272 (0.6); 2.264 (1.2); 2.252 (0.7); 2.117 (0.7); 2.105 (1.2); 2.093 (1.0); 2.090 (1.0); 2.086 (0.9); 2.082 (1.5); 2.078 (1.7); 2.074 (1.6); 2.070 (1.9); 2.067 (1.5); 2.062 (1.0); 2.059 (1.3); 2.055 (1.3); 2.043 (1.6); 2.035 (0.5); 2.032 (0.8); 1.878 (1.1); 1.865 (1.5); 1.852 (1.4); 1.844 (2.2); 1.830 (2.1); 1.821 (1.1); 1.808 (1.1); 1.795 (0.8); 1.532 (3.4); 0.008 (1.6); 0.000 (57.0); −0.009 (1.5)

[0443]

Example 460:1H-NMR (400.0 MHz, CDCl3): δ=8.208 (15.0); 8.202 (15.1); 8.159 (9.9); 8.153 (10.0); 7.620 (7.2); 7.613 (6.9); 7.599 (8.2); 7.592 (8.0); 7.519 (5.1); 7.432 (8.3); 7.425 (8.1); 7.411 (10.8); 7.404 (10.5); 7.361 (0.6); 7.350 (1.0); 7.345 (0.6); 7.317 (11.5); 7.316 (11.6); 7.310 (2.4); 7.306 (1.0); 7.302 (1.1); 7.297 (10.3); 7.295 (10.9); 7.290 (1.4); 7.287 (1.1); 7.280 (18.3); 7.279 (18.9); 7.275 (3.4); 7.274 (3.1); 7.273 (3.1); 7.2722 (3.6); 7.2715 (4.0); 7.271 (4.4); 7.270 (4.9); 7.268 (6.5); 7.2674 (7.1); 7.2666 (8.2); 7.266 (10.1); 7.265 (12.0); 7.260 (971.1); 7.234 (1.0); 7.232 (1.0); 7.175 (4.2); 7.168 (4.8); 7.162 (4.5); 7.154 (8.3); 7.146 (4.7); 7.140 (4.6); 7.132 (4.4); 7.011 (2.2); 7.001 (4.5); 6.996 (6.1); 6.993 (2.7); 6.989 (6.8); 6.983 (4.9); 6.978 (10.4); 6.971 (6.4); 6.968 (6.6); 6.965 (7.2); 6.960 (12.5); 6.953 (11.7); 6.950 (9.8); 6.942 (12.9); 6.938 (2.7); 6.932 (10.3); 6.924 (5.0); 6.921 (10.2); 6.910 (9.8); 6.902 (2.1); 6.899 (3.4); 6.887 (3.0); 6.853 (3.0); 6.846 (2.8); 6.839 (3.3); 6.832 (5.6); 6.824 (2.9); 6.818 (3.2); 6.811 (2.7); 4.353 (15.3); 4.336 (16.0); 4.143 (10.4); 4.121 (11.2); 3.751 (4.6); 3.735 (7.2); 3.713 (6.9); 3.696 (4.0); 3.654 (2.1); 3.645 (2.1); 3.632 (2.1); 3.624 (3.3); 3.617 (2.3); 3.604 (2.0); 3.594 (1.9); 3.528 (3.0); 3.425 (1.4); 3.401 (2.2); 2.370 (1.3); 2.360 (1.4); 2.355 (1.5); 2.346 (2.6); 2.335 (2.5); 2.325 (2.1); 2.320 (2.6); 2.311 (3.6); 2.302 (2.0); 2.297 (1.9); 2.287 (1.8); 2.185 (1.2); 2.175 (2.1); 2.159 (1.9); 2.145 (3.3); 2.138 (2.6); 2.131 (2.0); 2.124 (4.5); 2.110 (6.9); 2.104 (6.3); 2.091 (8.5); 2.080 (5.1); 2.075 (3.8); 2.070 (5.7); 2.056 (3.3); 2.046 (1.0); 2.035 (1.3); 2.005 (0.6); 1.544 (105.2); 1.361 (5.1); 1.276 (3.0); 0.146 (1.1); 0.069 (2.4); 0.049 (0.7); 0.033 (0.5); 0.008 (11.2); 0.006 (3.9); 0.0054 (4.4); 0.0046 (5.1); 0.000 (382.1); −0.005 (4.7); −0.006 (3.3); −0.007 (2.9); −0.009 (10.6); −0.011 (1.4); −0.0116 (1.1); −0.0124 (1.0); −0.013 (1.0); −0.014 (0.8); −0.015 (0.6); −0.016 (0.7); −0.020 (0.6); −0.023 (0.6); −0.028 (0.6); −0.150 (1.1)

[0444]

Example 1 (threo):1H-NMR (400.0 MHz, CDCl3): δ=8.189 (8.0); 8.183 (8.1); 7.892 (9.1); 7.886 (9.8); 7.875 (4.1); 7.868 (3.9); 7.856 (4.5); 7.853 (4.9); 7.850 (4.5); 7.847 (4.4); 7.835 (4.1); 7.828 (3.9); 7.773 (4.6); 7.766 (4.2); 7.754 (5.1); 7.752 (5.6); 7.748 (5.0); 7.745 (4.8); 7.733 (4.7); 7.727 (4.3); 7.521 (1.1); 7.339 (2.2); 7.323 (4.4); 7.318 (3.9); 7.307 (2.6); 7.302 (9.0); 7.297 (2.9); 7.286 (3.9); 7.281 (5.2); 7.262 (183.6); 7.189 (2.7); 7.173 (5.6); 7.168 (5.3); 7.157 (3.2); 7.152 (11.3); 7.147 (3.7); 7.136 (5.3); 7.131 (6.2); 7.115 (3.1); 7.019 (6.0); 7.011 (5.9); 6.998 (6.2); 6.990 (5.7); 6.968 (4.3); 6.964 (9.0); 6.947 (4.6); 6.942 (14.6); 6.937 (4.8); 6.920 (7.9); 6.916 (3.9); 6.870 (7.5); 6.862 (7.4); 6.849 (7.1); 6.841 (7.0); 6.787 (9.6); 6.765 (16.0); 6.743 (8.5); 4.359 (10.5); 4.334 (11.5); 4.280 (13.0); 4.252 (15.2); 3.923 (2.4); 3.913 (2.6); 3.895 (4.7); 3.885 (4.6); 3.866 (2.4); 3.857 (4.0); 3.846 (2.1); 3.831 (3.2); 3.820 (3.2); 3.806 (1.8); 3.794 (1.8); 3.744 (3.3); 3.733 (3.8); 3.729 (3.9); 3.717 (6.5); 3.706 (4.7); 3.702 (4.6); 3.691 (4.0); 3.619 (2.5); 3.608 (3.0); 3.604 (3.2); 3.592 (5.5); 3.581 (3.9); 3.577 (4.0); 3.566 (3.3); 3.485 (3.4); 3.472 (3.8); 3.461 (4.1); 3.457 (3.4); 3.449 (4.1); 3.445 (3.5); 3.434 (3.2); 3.422 (3.2); 3.414 (2.9); 3.402 (3.0); 3.391 (3.3); 3.387 (2.6); 3.379 (3.2); 3.375 (2.7); 3.364 (2.4); 3.352 (2.2); 2.569 (1.6); 2.559 (1.8); 2.554 (1.8); 2.545 (2.6); 2.535 (3.3); 2.524 (2.6); 2.520 (3.3); 2.511 (3.4); 2.502 (2.3); 2.497 (2.1); 2.487 (2.0); 2.332 (0.8); 2.328 (1.4); 2.325 (1.0); 2.317 (2.3); 2.309 (1.1); 2.305 (1.8); 2.300 (1.8); 2.293 (2.1); 2.288 (2.8); 2.283 (2.5); 2.277 (2.0); 2.270 (1.4); 2.266 (1.3); 2.262 (0.8); 2.254 (1.7); 2.246 (0.7); 2.242 (1.0); 2.239 (0.5); 2.104 (0.9); 2.093 (1.6); 2.081 (1.3); 2.077 (1.3); 2.074 (1.2); 2.070 (1.9); 2.066 (2.1); 2.062 (2.1); 2.058 (2.5); 2.054 (1.9); 2.050 (1.2); 2.046 (1.7); 2.043 (1.7); 2.031 (1.9); 2.019 (1.0); 1.879 (1.4); 1.866 (1.9); 1.854 (1.9); 1.844 (2.9); 1.830 (2.8); 1.821 (1.4); 1.810 (1.4); 1.796 (1.0); 1.584 (0.6); 1.564 (0.5); 1.540 (0.8); 1.464 (3.7); 1.333 (0.8); 1.284 (1.0); 1.274 (0.5); 1.255 (2.1); 0.008 (2.1); 0.000 (65.5); −0.009 (1.7)

[0445]

Example 14:1H-NMR (400.0 MHz, CDCl3): δ=8.069 (3.3); 8.066 (3.6); 8.063 (3.8); 8.060 (3.4); 7.879 (3.5); 7.873 (3.3); 7.859 (3.5); 7.853 (3.3); 7.791 (2.8); 7.785 (4.4); 7.767 (16.0); 7.761 (2.5); 7.520 (0.6); 7.355 (0.9); 7.339 (1.8); 7.334 (1.6); 7.323 (1.1); 7.318 (3.7); 7.313 (1.2); 7.302 (1.6); 7.297 (2.1); 7.281 (1.2); 7.261 (110.6); 7.226 (1.1); 7.210 (2.4); 7.205 (1.9); 7.194 (1.2); 7.189 (4.2); 7.184 (1.3); 7.173 (1.9); 7.168 (2.3); 7.152 (1.1); 6.997 (0.6); 6.979 (1.8); 6.975 (3.9); 6.958 (1.9); 6.953 (6.3); 6.948 (2.0); 6.932 (3.4); 6.927 (1.7); 6.825 (3.9); 6.803 (6.5); 6.781 (3.5); 5.299 (7.8); 4.368 (4.6); 4.343 (5.0); 4.276 (5.3); 4.247 (6.1); 4.044 (1.0); 3.933 (1.7); 3.919 (0.9); 3.909 (0.9); 3.891 (1.8); 3.881 (1.7); 3.862 (1.0); 3.855 (1.2); 3.845 (0.9); 3.831 (1.4); 3.819 (1.3); 3.806 (0.8); 3.794 (0.7); 3.756 (1.2); 3.745 (1.4); 3.741 (1.4); 3.729 (2.2); 3.718 (1.7); 3.714 (1.7); 3.703 (1.5); 3.650 (1.0); 3.638 (1.3); 3.635 (1.3); 3.623 (2.1); 3.611 (1.6); 3.609 (1.6); 3.597 (1.2); 3.484 (1.2); 3.472 (1.3); 3.461 (1.5); 3.457 (1.3); 3.449 (1.5); 3.445 (1.4); 3.439 (1.3); 3.434 (1.3); 3.427 (1.4); 3.422 (1.3); 3.416 (1.4); 3.412 (1.1); 3.404 (1.3); 3.401 (1.1); 3.389 (0.9); 3.378 (0.9); 2.556 (0.6); 2.546 (0.7); 2.541 (0.7); 2.532 (1.1); 2.522 (1.3); 2.511 (1.0); 2.507 (1.3); 2.498 (1.4); 2.488 (0.9); 2.484 (0.8); 2.473 (0.7); 2.323 (0.5); 2.312 (0.9); 2.300 (0.7); 2.295 (0.7); 2.288 (0.8); 2.284 (1.1); 2.277 (0.9); 2.273 (0.8); 2.266 (0.5); 2.261 (0.5); 2.249 (0.7); 2.107 (0.7); 2.095 (0.5); 2.092 (0.5); 2.084 (0.9); 2.080 (0.9); 2.076 (0.8); 2.072 (1.1); 2.069 (0.9); 2.060 (0.7); 2.057 (0.7); 2.049 (0.5); 2.045 (0.9); 1.902 (0.6); 1.889 (0.9); 1.877 (0.8); 1.867 (1.3); 1.853 (1.2); 1.843 (0.6); 1.832 (0.6); 1.562 (0.9); 0.008 (1.1); 0.000 (37.9); −0.009 (1.1)

[0446]

Example 14 (three):1H-NMR (400.0 MHz, CDCl3): δ=7.791 (2.8); 7.785 (4.4); 7.767 (16.0); 7.760 (2.5); 7.519 (0.7); 7.272 (0.6); 7.271 (0.6); 7.270 (0.7); 7.2694 (0.8); 7.2687 (0.9); 7.268 (1.0); 7.267 (1.2); 7.266 (1.5); 7.265 (1.8); 7.261 (119.0); 7.254 (0.8); 7.253 (0.6); 7.227 (1.0); 7.210 (2.1); 7.206 (2.0); 7.194 (1.2); 7.189 (4.3); 7.185 (1.4); 7.173 (2.0); 7.168 (2.4); 7.152 (1.2); 6.997 (0.7); 6.825 (4.0); 6.803 (6.6); 6.782 (3.5); 4.275 (5.3); 4.247 (6.2); 3.919 (0.9); 3.909 (1.0); 3.891 (1.8); 3.881 (1.7); 3.863 (0.8); 3.853 (0.8); 3.758 (0.8); 3.744 (1.1); 3.732 (1.6); 3.720 (1.3); 3.706 (1.0); 3.487 (0.8); 3.475 (0.9); 3.462 (1.1); 3.451 (1.2); 3.436 (0.7); 3.424 (0.7); 2.558 (0.6); 2.548 (0.7); 2.544 (0.7); 2.534 (1.1); 2.524 (1.3); 2.514 (1.0); 2.510 (1.3); 2.500 (1.4); 2.491 (0.9); 2.486 (0.8); 2.476 (0.7); 2.325 (0.5); 2.313 (0.9); 2.302 (0.7); 2.296 (0.7); 2.293 (0.6); 2.289 (0.8); 2.285 (1.1); 2.278 (1.0); 2.274 (0.8); 2.267 (0.5); 2.250 (0.7); 1.550 (3.5); 1.333 (0.8); 0.008 (1.2); 0.000 (42.6); −0.009 (1.2)

[0447]

The retention time (Rt) given in the Rt table below for the enantiomer of the formula (I) in question is given in minutes (min), where the letter a, b, c or d given after the forward slash after the retention time refers to the conditions stated above for HPLC on a chiral column and the respective mobile phase stated above, i.e. mobile phase a, mobile phase b, mobile phase c or mobile phase d.

[0000]

Rt in min, where R1is in each case hydrogen
No.Q(R2)n(R3)merythro-1erythro-2threo-1threo-2
16-fluoropyridin-3-yl2.6-F213.319/c16.632/c18.098/c25.226/c
65-bromopyridin-3-yl2.6-F212.165/c14.334/c16.747/c22.114/c
145-chloro-6-fluoropyridin-3-yl2.6-F229.016/d32.963/d43.280/d45.023/d
85pyridin-3-yl2.6-F211.160/b16.121/b17.456/b32.753/b
4606-chloropyridin-3-yl2.5-F211.890/c14.276/c23.034/c27.864/c
4725-chloro-6-fluoropyridin-3-yl2.5-F2 6.190/c 6.827/c11.531/c13.014/c

FORMULATION EXAMPLES

[0000]

  • a) A dust is obtained by mixing 10 parts by weight of a compound of the formula (I) and 90 parts by weight of talc as inert substance and comminuting the mixture in a hammer mill.
  • b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of a compound of the formula (I), 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as wetting agent and dispersant, and grinding the mixture in a pinned-disk mill.
  • c) A readily water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of a compound of the formula (I) with 6 parts by weight of alkylphenol poly glycol ether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range for example about 255 to about 277° C.) and grinding the mixture in a ball mill to a fineness of below 5 microns.
  • d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier.
  • e) Water-dispersible granules are obtained by mixing
    • 75 parts by weight of a compound of the formula (I),
    • 10 parts by weight of calcium lignosulfonate,
    • 5 parts by weight of sodium lauryl sulfate,
    • 3 parts by weight of polyvinyl alcohol and
    • 7 parts by weight of kaolin,
    • grinding the mixture in a pinned-disk mill, and granulating the powder in a fluidized bed by spray application of water as a granulating liquid.
  • f) Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill,
    • 25 parts by weight of a compound of the formula (I),
    • 5 parts by weight of sodium 2,2′-dinaphthylmethane-6,6′-disulfonate,
    • 2 parts by weight of sodium oleoylmethyltaurinate,
    • 1 part by weight of polyvinyl alcohol,
    • 17 parts by weight of calcium carbonate and
    • 50 parts by weight of water,
    • then grinding the mixture in a bead mill and atomizing and drying the resulting suspension in a spray tower by means of a one-phase nozzle.

[0467]

Biological Examples

[0468]

Herbicidal Pre-Emergence Action

[0469]

Seeds of monocotyledonous and dicotyledonous weed plants and crop plants were placed in wood-fiber pots in sandy loam and covered with soil. The compounds (I) according to the invention, formulated in the form of wettable powders (WP), were then applied as aqueous suspension or emulsion at a water application rate of 600 l/ha (converted) with the addition of 0.2% of wetting agent to the surface of the covering soil.

[0470]

After the treatment, the pots were placed in a greenhouse and kept under good growth conditions for the test plants. After about 3 weeks, the effect was scored visually in comparison with untreated controls as percentages. For example, 100% activity=the plants have died, 50% herbicidal activity or damage=the plants have been reduced by 50% or the plant mass has been reduced by 50%, 0% activity=like control plants.

[0471]

The results obtained show that compounds (I) according to the invention and their salts, in particular the compounds according to the invention characterized as preferred, have good to very good herbicidal activity against harmful plants at an application rate of 320 g or less per hectare, generally also even at a respective application rate of 80 g/ha.

[0472]

The biological tests were carried out in each case separately with the compounds according to the invention below which, by virtue of the good to very good herbicidal activity thereof, are particularly preferred according to the invention:

[0473]

Compound No. 1, 2, 3, 4, 5, 6, 14, 15, 85, 86, 186, 460, 461, 462, 463, 472, 543, 544, 1833, 1834, 1835, 1836, 1873, 1875, 1876, 1915, 1961, 1962, 1963, 1964, 2001, 2003, 2004, 2005, 2006 and 2043.

[0474]

The biological tests were in each case carried out separately with the following compounds according to the invention: Compound No. 1 erythro+threo-1, 1 threo-2, 14 erythro-1+erythro-2, 14 threo-1, 14 threo-2, 15 erythro-1+erythro-2, 15 threo-1+threo-2, 460 erythro, 460 erythro-1, 460 threo, 460 threo-1, 460 threo-2, 472 erythro-1, 472 erythro-2, 472 threo-1, 472 threo-2, 6 erythro-2, 6 erythro-1, 6 threo-1, 6 threo-2 and 85 erythro.

[0475]

Here, these compounds according to the invention were in each case employed in the biological tests as a component of a wettable powder (WP formulation).

[0476]

At an application rate of 320 g/ha, all the compounds according to the invention mentioned showed 80% to 100% herbicidal activity in the biological tests, against one, more than one or all of the harmful plants below:

[0000]

ALOMY=Alopecurus myosuroides
AVEFA=Avena fatua
CYPES=Cyperus esculentus
ECHCG=Echinochloa crus-galli
LOLMU=Lolium multiflorum
SETVI=Setaria viridis
ABUTH=Abutilon theophrasti
AMARE=Amaranthus retroflexus
POLCO=Polygonum convolvulus (=Fallopia convolvulus)
STEME=Stellaria media
VIOTR=Viola tricolor
VERPE=Veronica persica

[0477]

What was determined was the respective herbicidal activity, in each case at the same point in time after application of the formulation in question, i.e. the damage to the respective harmful plant in %.

[0478]

Furthermore, the compounds according to the invention mentioned above were applied to the following useful plants, in each case at the application rates mentioned.

[0000]

ORYSA=Oryza sativa (common rice)
TRZAS=triticum aestivum (spring) (summer wheat)
ZEAMX=Zea mays (maize)
BRSNW=Brassica napus subsp. napus (winter) (winter oilseed rape)

[0479]

Here, the observed damage to the respective useful plants was within the acceptable range and was generally assessed as low (generally in the range from 0 to 20%, mostly in the range from 0 to 10%).

[0480]

Herbicidal Post-Emergence Action

[0481]

Seeds of monocotyledonous and dicotyledonous weeds and crop plants were placed in sandy loam in wood-fiber pots, covered with soil and cultivated in a greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants were treated at the one-leaf stage, where the compounds according to the invention, formulated in the form of wettable powders (WP), were applied by spraying as aqueous suspension or emulsion at a water application rate of 600 l/ha (converted) with the addition of 0.2% of wetting agent to the green parts of the plants. After the test plants had been kept in the greenhouse under optimum growth conditions for about 3 weeks, the activity of the preparations was rated visually in comparison to untreated controls in percent (%). For example, 100% activity=the plants have died, 50% herbicidal activity or damage=the plants have been reduced by 50% or the plant mass has been reduced by 50%, 0% activity=like control plants.



Primarily, the present invention relates to compounds of the formula (I) defined below and to their use as herbicides, in particular for controlling broad-leaved weeds and/or weed grasses in crops of useful plants and/or as plant growth regulators for influencing the growth of crops of useful plants. The present invention also relates to herbicidal or plant growth-regulating compositions comprising one or more compounds of the formula (I). Moreover, the present invention relates to processes for preparing the compounds of the formula (I).



1. A compound of formula (I) and/or salt thereof,

wherein

Q represents a mono- or bicyclic heteroaromatic radical with in total 1 to 9 carbon ring atoms, where the heteroatom or heteroatoms in the heteroaromatic ring are selected from the group consisting of N, O, S, P, B, Si, and Se,

R1represents hydrogen or a hydrolyzable radical,

(R2)nrepresent n substituents R2, where R2(if n=1) or each of the substituents R2(if n is greater than 1) independently of one another represents halogen, cyano, nitro, (C1-C8)alkyl, (C1-C8)alkoxy, (C1-C8)alkylthio, (C1-C8)alkylsulfinyl, (C1-C8)alkylsulfonyl, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy, (C1-C6)haloalkylthio, (C1-C6)haloalkylsulfinyl, (C1-C6)haloalkylsulfonyl, (C2-C6)alkenyl, (C2-C6)alkynyl, tri-[(C1-C4)alkyl]silyl or tri-[(C1-C4)alkyl]silyl-(C1-C4)alkyl,

or in each case two R2directly adjacent on the heteroaromatic radical Q are together a group of the formula —Z1-A*1-Z2—, in which

A* represents an alkylene group having 1 to 4 carbon atoms which is optionally substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy,

Z1represents a direct bond, O or S and

Z2represents a direct bond, O or S,

where the group —Z1-A*-Z2— together with the atoms of the heteroaromatic radical Q bonded to this group Q form a 5- or 6-membered ring, and

(R3)mrepresents m substituents R3,

where R3(if m=1) or each of the substituents R3(if m is greater than 1) independently of one another represents halogen, cyano, nitro, (C1-C8)alkyl, (C1-C8)alkoxy, (C1-C8)alkylthio, (C1-C8)alkylsulfinyl, (C1-C8)alkylsulfonyl, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy, (C1-C6)haloalkylthio, (C1-C6)haloalkylsulfinyl, (C1-C6)haloalkylsulfonyl, (C2-C6)alkenyl, (C2-C6)alkynyl, tri-[(C1-C4)alkyl]silyl, tri-[(C1-C4)alkyl]silyl-(C1-C4)alkyl or —NR*R**, where R* and R**, independently of one another and independently of any other radicals —NR*R** present, are in each case selected from the group consisting of H, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C4)alkoxy-(C1-C4)alkyl, (C1-C6)alkanoyl, [(C1-C4)haloalkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, [(C1-C4)haloalkoxy]carbonyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkyl-(C1-C4)alkyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkenyl-(C1-C4)alkyl, phenyl and phenyl-(C1-C4)alkyl, where each of the specified radicals (C3-C6)cycloalkyl, (C3-C6)cycloalkyl-(C1-C4)alkyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkenyl-(C1-C4)alkyl, phenyl and phenyl-(C1-C4)alkyl is substituted in the cycle optionally by one or more identical or different radicals Rbb, where

Rbbin each case represents halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy or (C1-C4)haloalkoxy and, in the case of (C3-C6)cycloalkyl, (C3-C6)cycloalkyl-(C1-C4)alkyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkenyl-(C1-C4)alkyl, Rbbmay additionally represent oxo, or

NR*R** represents a 3- to 8-membered heterocycle which, in addition to this nitrogen atom, optionally contains one or two further ring heteroatoms selected from the group consisting of N, O and S and which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)alkyl, (C1-C4)haloalkyl and oxo,

or where in each case two groups R3directly adjacent on the ring together represent a group of the formula —Z3-A**-Z4—, in which

A** represents an alkylene group having 1 to 4 carbon atoms which is optionally substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy,

Z3represents a direct bond, O or S and

Z4represents a direct bond, O or S,

where the group —Z3-A**-Z4together with the carbon atoms, bonded to this group, of the phenyl ring form a 5- or 6-membered ring,

n represents 0, or an integer in the range from 1 to 5, optionally 0, 1, 2 or 3, and

m represents 0, 1, 2, 3, 4 or 5, optionally 0, 1, 2 or 3.

2. The compound of formula (I) and/or salt thereof according to claim 1, wherein

Q represents a mono- or bicyclic heteroaromatic radical having in total 2 to 9 carbon ring atoms, where the heteroaromatic radical Q contains 1, 2, 3 or 4 heteroatoms in the heteroaromatic ring and the heteroatom or the heteroatoms are selected from the group consisting of N, O, and S.

3. The compound of formula (I) and/or salt thereof as claimed in claim 1, wherein

Q represents a mono- or bicyclic heteroaromatic radical selected from the group consisting of pyrimidinyl, pyridinyl, pyridazinyl, pyrazinyl, thienyl, furyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, triazinyl, quinolyl, isoquinolyl, cinnolinyl-, quinazolinyl, quinoxalinyl, pteridinyl, indolyl and phthalazinyl.

4. The compound of formula (I) and/or salt thereof as claimed in claim 1, wherein the compound of the formula (I) corresponds to the formula (I-1), (I-2) or (I-3) defined below

5. The compound of formula (I) and/or salt thereof as claimed in claim 1, wherein

R1represents hydrogen or a hydrolyzable radical having in total up to 30 carbon atoms, with preference a hydrolyzable radical having in total 1 to 24 carbon atoms, optionally having in total 1 to 20 carbon atoms.

6. The compound of formula (I) and/or salt thereof as claimed in claim 1, wherein

R1represents hydrogen or a hydrolyzable radical having in total 1 to 24 carbon atoms, where R1

represents an optionally substituted hydrocarbon radical or an optionally substituted heterocyclyl radical, or

Rbrepresents a radical of the formula SiRaRbRc, or —NRaRb,

where each of the radicals Raand Rbindependently of the other represents hydrogen or an optionally substituted hydrocarbon radical and Rcindependently represents an optionally substituted hydrocarbon radical, or —NRaRbrepresents a 3- to 9-membered heterocycle which, in addition to this nitrogen atom, may contain one or two further ring heteroatoms from the group consisting of N, O and S and which is substituted or unsubstituted, or

represents a radical of the formula —C(═O)—Reor —P(═O)(Rf)2, where Reand both radicals Rfin each case independently of one another are selected from the group consisting of hydrogen, OH, unsubstituted or substituted (C1-C8)alkyl, unsubstituted or substituted (C1-C4)haloalkyl, unsubstituted or substituted (C2-C8)alkenyl, unsubstituted or substituted (C2-C8)alkynyl, unsubstituted or substituted (C1-C6)alkoxy, unsubstituted or substituted (C1-C6)alkoxy-(C1-C8)alkyl, unsubstituted or substituted (C1-C4)haloalkoxy, unsubstituted or substituted (C1-C4)haloalkoxy-(C1-C8)alkyl, unsubstituted or substituted (C3-C8)alkenyloxy, unsubstituted or substituted (C3-C8)alkenyloxy-(C1-C8)alkyl, unsubstituted or substituted (C3-C8)alkynyloxy, unsubstituted or substituted (C3-C8)alkynyloxy-(C1-C8)alkyl, unsubstituted or substituted —NR*R**, where R* and R** are as defined above, unsubstituted or substituted tri-[(C1-C4)alkyl]silyl, unsubstituted or substituted tri-[(C1-C4)alkyl]silyl-(C1-C8)alkyl, unsubstituted or substituted (C3-C6)cycloalkyl, unsubstituted or substituted (C3-C6)cycloalkyl-(C1-C8)alkyl, unsubstituted or substituted (C5-C6)cycloalkenyl, unsubstituted or substituted (C5-C6)cycloalkenyl-(C1-C8)alkyl, unsubstituted or substituted (C5-C6)cycloalkynyl, unsubstituted or substituted (C5-C6)cycloalkynyl-(C1-C8)alkyl, unsubstituted or substituted phenyl, unsubstituted or substituted phenyl-(C1-C8)alkyl, unsubstituted or substituted phenoxy, unsubstituted or substituted phenoxy-(C1-C8)alkyl, unsubstituted or substituted phenylamino, unsubstituted or substituted phenylamino(C1-C8)alkyl, unsubstituted or substituted Het, unsubstituted or substituted Het-(C1-C6)alkyl and unsubstituted or substituted Het-O—(C1-C6)alkyl, where

Het in each case represents a saturated, partially unsaturated or heteroaromatic monocyclic heterocyclyl radical having 3 to 9 ring atoms or a 9- or 10-membered bicyclic heterocycle in each case containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where each of the specified substituted radicals is substituted in the acyclic moiety by one or more identical or different radicals RAand/or where each of the specified substituted radicals is substituted in the cyclic moiety by one or more identical or different radicals RB, where

RArepresents halogen, cyano, hydroxy or (C1-C6)alkoxy, and

RBindependently of any further radicals RBpresent is selected from the group consisting of halogen, cyano, hydroxy, oxo, nitro, (C1-C8)alkyl, (C1-C6)haloalkyl, cyano-(C1-C6)alkyl, hydroxy-(C1-C6)alkyl, nitro-(C1-C6)alkyl, (C2-C8)alkenyl, (C2-C8)haloalkenyl, (C2-C8)alkynyl, (C2-C8)haloalkynyl, (C1-C8)alkoxy, (C2-C8)alkenyloxy, (C2-C8)alkynyloxy, (C1-C8)haloalkoxy, (C1-C6)alkoxy-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C4)alkoxy, (C1-C6)haloalkoxy-(C1-C4)alkyl, (C1-C6)haloalkoxy-(C1-C4)alkoxy, (C1-C8)alkylthio, (C2-C6)alkenylthio, (C2-C6)alkynylthio, (C1-C8)alkylsulfinyl, (C1-C6)haloalkylsulfinyl, (C1-C8)alkylsulfonyl, (C1-C6)haloalkylsulfonyl, Raa—C(═O)—, Raa—C(═O)—(C1-C6)alkyl, —NR*R**, tri-[(C1-C4)alkyl]silyl, tri-[(C1-C4)alkyl]silyl-(C1-C6)alkyl, (C3-C8)cycloalkyl, (C3-C8)cycloalkoxy, (C3-C8)cycloalkyl-(C1-C8)alkyl, (C3-C8)cycloalkyl-(C1-C8)alkoxy, phenyl, phenyl-(C1-C8)alkyl, phenoxy, phenoxy-(C1-C8)alkyl, phenylamino, phenylamino-(C1-C8)alkyl or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where each of these specified radicals can be substituted in the cyclic moiety by one or more identical or different Rbb, where

Raain each case independently of one another represent hydrogen, OH, (C1-C8)alkyl, (C1-C6)haloalkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C8)alkoxy, (C1-C6)alkoxy-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkyloxy, (C1-C6)haloalkoxy, (C1-C6)haloalkoxy-(C1-C6)alkyl, (C1-C6)haloalkoxy-(C1-C6)alkoxy, (C3-C8)alkenyloxy, (C3-C8)alkenyloxy-(C1-C6)alkyl, (C3-C8)alkenyloxy-(C1-C6)alkoxy, (C3-C8)alkynyloxy, (C3-C8)alkynyloxy-(C1-C6)alkyl, (C3-C8)alkynyloxy-(C1-C6)alkoxy, —NR*R**, tri-[(C1-C4)alkyl]silyl, tri-[(C1-C4)alkyl]silyl-(C1-C6)alkyl, tri-[(C1-C4)alkyl]silyl-(C1-C6)alkoxy, (C3-C8)cycloalkyl, (C3-C8)cycloalkoxy, (C3-C8)cycloalkyl-(C1-C8)alkyl, (C3-C8)cycloalkyl-(C1-C8)alkoxy, (C5-C8)cycloalkenyl, (C5-C8)cycloalkenyl-(C1-C6)alkyl, (C5-C8)cycloalkenyloxy, (C5-C8)cycloalkynyl, (C5-C8)cycloalkynyl-(C1-C6)alkyl, (C5-C8)cycloalkynyl-(C1-C6)alkoxy, phenyl, phenyl-(C1-C8)alkyl, phenyl-(C1-C8)alkoxy, phenoxy, phenoxy-(C1-C8)alkyl, phenoxy-(C1-C8)alkoxy, phenylamino, phenylamino-(C1-C8)alkyl, phenylamino-(C1-C8)alkoxy or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle containing 1, 2, 3 or 4 heteroatoms and optionally bonded via an alkylene group or an alkoxy group is selected from the group consisting of O, N and S, where each of the radicals Raaencompassing a cycle is optionally substituted in the cyclic moiety by one or more identical or different radicals Rbb, and where

R*, R**, —NR*R** and Rbbhave the meaning given above.

7. The compound of formula (I) and/or salt thereof as claimed in claim 1, wherein

R1represents hydrogen, unsubstituted (C1-C18)alkyl, unsubstituted (C2-C18)alkenyl, unsubstituted (C2-C18)alkynyl, substituted (C1-C18)alkyl, substituted (C2-C18)alkenyl or substituted (C2-C18)alkynyl, where in the case of substituted (C1-C18)alkyl, substituted (C2-C18)alkenyl and substituted (C2-C18)alkynyl the substituent(s) is/are each independently of one another selected from groups (a)-(e) below:

(a) halogen, cyano, thio, nitro, hydroxy, carboxy, (C1-C8)alkoxy, (C2-C8)alkenyloxy, (C2-C8)alkynyloxy, (C1-C8)haloalkoxy, (C1-C4)alkoxy-(C1-C4)alkoxy, (C1-C8)alkylthio, (C2-C8)alkenylthio, (C2-C8)alkyinylthio, (C1-C8)haloalkylthio, (C2-C8)haloalkenylthio, (C2-C8)haloalkinylthio, (C1-C8)alkylsulfinyl, (C2-C8)alkenyl sulfinyl, (C2-C8)alkynylsulfinyl, (C1-C8)haloalkylsulfinyl, (C2-C8)haloalkenylsulfinyl, (C2-C8)haloalkinylsulfinyl, (C1-C8)alkylsulfonyl, (C2-C8)alkenyl sulfonyl, (C2-C8)alkynylsulfonyl, (C1-C8)haloalkylsulfonyl, (C2-C8)haloalkenyl sulfonyl, (C2-C8)haloalkynylsulfonyl, —NR*R**,

where R*, R** and —NR*R** in each case have the meaning given above,

(b) (C3-C8)cycloalkyl, (C5-C8)cycloalkenyl, (C5-C8)cycloalkinyl, (C3-C8)cycloalkyl-(C1-C6)alkoxy, (C3-C8)cycloalkyl-(C1-C6)alkyl-S(O)p—, (C5-C8)cycloalkenyl-(C1-C6)alkoxy, (C5-C8)cycloalkenyl-(C1-C6)alkyl-S(O)p—, (C5-C8)cycloalkynyl-(C1-C6)alkoxy, (C5-C8)cycloalkynyl-(C1-C6)alkyl-S(O)p—, (C3-C8)cycloalkoxy, (C3-C8)cycloalkyl-S(O)p—, (C5-C8)cycloalkenyloxy, (C5-C8)cycloalkenyl-S(O)p—, (C5-C8)cycloalkynyloxy, (C5-C8)cycloalkynyl-S(O)p—, (C3-C8)cycloalkoxy-(C1-C6)alkoxy, (C3-C8)cycloalkoxy-(C1-C6)alkyl-S(O)p—, phenyl, phenyl(C1-C6)alkoxy, phenoxy, phenyl-S(O)p—, phenyl-(C1-C6)alkyl-S(O)p—, phenoxy-(C1-C6)alkoxy, phenoxy-(C1-C6)alkyl-S(O)p—, a radical Het1, Het1-S(O)p—, Het1-(C1-C6)alkoxy, Het1-O—, Het1-O—(C1-C6)alkoxy, where the radical Het1has the meaning given above, and where each of the last-mentioned radicals of the group (b) in the acyclic moiety is unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, hydroxy and (C1-C6)alkoxy, and/or in the cyclic moiety is unsubstituted or substituted by one or more identical or different radicals RB, where RBhas the meaning given above, and the index p is in each case 0, 1 or 2,

(c) —C(═O)—RC, —C(═O)—O—RC, —O—C(═O)—RC, —O—C(═O)—O—RC, —C(═O)—S—RC, —C(═S)—S—RC, —C(═O)—NR*R**, —C(═O)—O—NR*R**, —O—C(═O)—NR*R**, —N(R*)—C(═O)—RC, —N(R*)—C(═O)—NR*R**, —N(R*)—C(═O)—O—RC, —P(═O)(RC)(RD), —P(═O)(ORC)(RD), —P(═O)(ORC)(ORD) or —O—P(═O)(ORC)(ORD),

where R*, R** and —NR*R** in each case have the meaning given above and RCand RDare as defined below,

(d) —SiR′3, —O—SiR′3, (R′)3Si—(C1-C6)alkoxy, —CO—O—NR′2, —O—N═CR′2, —N═CR′2, —O—NR′2, —CH(OR′)2and —O—(CH2)q—CH(OR′)2, in which each of the radicals R′ is independently selected from the group consisting of H, (C1-C4)alkyl or phenyl which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)haloalkyl, (C1-C4)haloalkoxy and nitro or substituted at two adjacent positions by a (C2-C6)alkylene bridge, and the index q represents an integer from 0 to 6, and

(e) R″O—CHR′″ CH(OR″)—(C1-C6)alkoxy,

in which each of the radicals R″ independently of the others represents H or (C1-C4)-alkyl or together the radicals represent a (C1-C6)-alkylene group and R′″ represents H or (C1-C4)-alkyl,

or

R1(C3-C9)cycloalkyl, (C5-C9)cycloalkenyl, (C5-C9)cycloalkynyl or phenyl,

where each of these radicals is unsubstituted or substituted by one or more radicals from the group consisting of the radicals of subgroups (a′)-(e′) below:

(a′) halogen, cyano, thio, nitro, hydroxy, carboxy, (C1-C8)alkyl, (C1-C8)haloalkyl, (C1-C4)alkoxy-(C1-C4)alkyl, (C2-C8)alkenyl, (C2-C8)haloalkenyl, (C2-C8)alkynyl, (C2-C8)haloalkynyl, (C1-C8)alkoxy, (C2-C8)alkenyloxy, (C2-C8)alkynyloxy, (C1-C8)haloalkoxy, (C1-C4)alkoxy-(C1-C4)alkoxy, (C1-C8)alkylthio, (C2-C8)alkenylthio, (C2-C8)alkynylthio and —NR*R**, where R*, R**, —NR*R**, and Rbbin each case have the meaning given above,

(b′) radicals of the formulae —C(═O)—RC, —C(═O)—O—RC, —O—C(═O)—RC, —O—C(═O)—O—RC, —C(═O)—S—RC, —C(═S)—S—RC, —C(═O)—NR*R**, —C(═O)—O—NR*R**, —O—C(═O)—NR*R**, —N(R*)—C(═O)—RC, —N(R*)—C(═O)—NR*R**, —N(R*)—C(═O)—O—RC, —P(═O)(RC)(RD), —P(═O)(ORC)(RD), —P(═O)(ORC)(ORD) or —O—P(═O)(ORC)(ORD),

where R*, R**, —NR*R** and Rbbin each case have the meaning given above and RCand RDhave the meaning defined below,

(c′) radicals of the formulae —SiR′3, —O—SiR′3, (R′)3Si—(C1-C6)alkoxy, —CO—O—NR′2, —O—N═CR′2, —N═CR′2, —O—NR′2, —CH(OR′)2and —O—(CH2)q—CH(OR′)2,

in which each of the radicals R1independently of the others represents H, (C1-C4)-alkyl or phenyl which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy and nitro or is substituted at two adjacent positions by a (C2-C6)-alkylene bridge, and q represents an integer from 0 to 6, and

(d′) radicals of the formula R″O—CHR′″CH(OR″)—(C1-C6)alkoxy,

in which each of the radicals R″ independently of the others represents H or (C1-C4)-alkyl or together the radicals represent a (C1-C6)-alkylene group and R′″ represents H or (C1-C4)-alkyl, and

(e′) a radical of the formula Het1which is unsubstituted or substituted by one or more identical or different radicals RB, where RBhas the meaning given above,

or

R1represents a polycyclic radical based on (C3-C9)cycloalkyl, (C5-C9)cycloalkenyl, (C5-C9)cycloalkynyl or phenyl, where the base ring is fused with a carbocyclic or heterocyclic ring, and where the base ring or the polycyclic system is unsubstituted or substituted by one or more identical or different radicals RB, where RBhas the meaning given above,

or

R1represents a heterocyclic radical Het1which is unsubstituted in the ring or in the polycyclic system or substituted by one or more identical or different radicals RB, where RBhas the meaning given above,

where

Het1in each case independently of the others is a saturated, partially unsaturated or heteroaromatic monocyclic heterocyclyl radical having 3 to 9 ring atoms, optionally having 5 or 6 ring atoms, or a 9- or 10-membered bicyclic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, optionally a 5- or 6-membered heterocycle having 1 to 3 ring heteroatoms from the group consisting of N, O and S which is optionally also fused to a carbocyclic or heterocyclic ring, optionally a carbocyclic ring having 3 to 6 carbon atoms or a heterocyclic ring having 5 or 6 ring atoms and 1 to 3 ring heteroatoms from the group consisting of N, O and S, optionally benzo-fused,

RAhas the meaning given above,

RBhas the meaning given above, and where RBoptionally represents a radical selected from the group consisting of halogen, cyano, hydroxy, oxo, nitro, (C1-C6)alkyl, (C1-C4)haloalkyl, cyano-(C1-C4)alkyl, hydroxy-(C1-C4)alkyl, nitro-(C1-C4)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, (C2-C6)alkynyl, (C2-C6)haloalkynyl, (C1-C6)alkoxy, (C2-C6)alkenyloxy, (C2-C6)alkynyloxy, (C1-C6)haloalkoxy, (C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)alkoxy-(C1-C4)alkoxy, (C1-C4)haloalkoxy-(C1-C4)alkyl, (C1-C4)haloalkoxy-(C1-C4)alkoxy, (C1-C6)alkylthio, (C2-C6)alkenylthio, (C2-C6)alkynylthio, (C1-C6)alkylsulfinyl, (C1-C6)haloalkylsulfinyl, (C1-C6)alkylsulfonyl, (C1-C6)haloalkylsulfonyl, a radical of the formulaaa—C(═O)— or Raa—C(═O)—(C1-C6)alkyl, where Raahas the meaning given above, —NR*R**, where R*, R**, —NR*R**, and Rbbin each case have the meaning given above, tri-[(C1-C4)alkyl]silyl, tri-[(C1-C4)alkyl]silyl-(C1-C6)alkyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkoxy, (C3-C6)cycloalkyl-(C1-C4)alkyl, (C3-C6)cycloalkyl-(C1-C8)alkoxy, phenyl, phenyl-(C1-C6)alkyl, phenoxy, phenoxy-(C1-C6)alkyl, phenylamino, phenylamino-(C1-C6)alkyl, or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where each of the radicals RBin the cyclic moiety is optionally substituted by one or more identical or different radicals Rbb, where RBand Rbbin each case have the meaning given above,

RCand RDeach independently of one another (and also independently of radicals RC, RDin other groups) represent a radical selected from the group consisting of:

(i) hydrogen, unsubstituted (C1-C8)alkyl, unsubstituted (C2-C8)alkenyl, unsubstituted (C2-C8)alkynyl, substituted (C1-C8)alkyl, substituted (C2-C8)alkenyl, or substituted (C2-C8)alkynyl, where each of these substituted radicals is substituted by one or more radicals from the group halogen, cyano, nitro, hydroxy, (C1-C6)alkoxy, (C2-C6)alkenyloxy, (C2-C6)alkynyloxy, (C1-C8)haloalkoxy, (C1-C4)alkoxy-(C1-C4)alkoxy, (C1-C8)alkylthio, (C1-C8)haloalkylthio, (C1-C8)alkylsulfinyl, (C1-C8)haloalkylsulfinyl, (C1-C8)alkylsulfonyl, (C1-C8)haloalkylsulfonyl and tri-[(C1-C4)alkyl]silyl,

and

(ii) (C3-C8)cycloalkyl, (C5-C8)cycloalkenyl, (C5-C8)cycloalkynyl, phenyl, (C3-C8)cycloalkyl-(C1-C6)alkyl, (C5-C8)cycloalkenyl-(C1-C6)alkyl, (C5-C8)cycloalkynyl-(C1-C6)alkyl, phenyl-(C1-C6)alkyl, (C3-C8)cycloalkyloxy-(C1-C6)alkyl, (C3-C8)cycloalkyl-S(O)p—(C1-C6)alkyl, (C5-C8)cycloalkenyloxy-(C1-C6)alkyl, (C5-C8)cycloalkynyloxy-(C1-C6)alkyl, phenoxy-(C1-C6)alkyl, phenyl-S(O)p—(C1-C6)alkyl, (C3-C8)cycloalkylamino-(C1-C6)alkyl, (C5-C8)cycloalkenylamino-(C1-C6)alkyl, (C5-C8)cycloalkynylamino-(C1-C6)alkyl, phenylamino-(C1-C6)alkyl, Het1, Het1-(C1-C6)alkyl, Het1-O—(C1-C6)alkyl or Het1-S(O)p—(C1-C6)alkyl, where Het1has the meaning given above, and where each of these radicals is unsubstituted in the acyclic moiety or substituted by one or more identical or different radicals RAand in the cyclic moiety is unsubstituted or substituted by one or more identical or different radicals RBand p in each case represents 0, 1 or 2, where RAand RBin each case have the meaning given above,

Raahas the meaning given above, and where Raaoptionally independently is a radical selected from the group consisting of hydrogen, OH, (C1-C6)alkyl, (C1-C4)haloalkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)alkoxy-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkyloxy, (C1-C4)haloalkoxy, (C1-C4)haloalkoxy-(C1-C6)alkyl, (C1-C4)haloalkoxy-(C1-C6)alkoxy, (C3-C6)alkenyloxy, (C3-C6)alkenyloxy-(C1-C6)alkyl, (C3-C6)alkenyloxy-(C1-C6)alkoxy, (C3-C6)alkynyloxy, (C3-C6)alkynyloxy-(C1-C6)alkyl, (C3-C6)alkynyloxy-(C1-C6)alkoxy, —NR*R**, where R* and R** are as defined above, tri[(C1-C4)alkyl]silyl, tri[(C1-C4)alkyl]silyl-(C1-C6)alkyl, tri[(C1-C4)alkyl]silyl-(C1-C6)alkoxy, (C3-C6)cycloalkyl, (C3-C6)cycloalkoxy, (C3-C6)cycloalkyl-(C1-C8)alkyl, (C3-C6)cycloalkyl-(C1-C8)alkoxy, (C5-C6)cycloalkenyl, (C5-C6)cycloalkenyl-(C1-C6)alkyl, (C5-C6)cycloalkenyloxy, (C5-C6)cycloalkynyl, (C5-C6)cycloalkynyl-(C1-C6)alkyl, (C5-C6)cycloalkynyl-(C1-C6)alkoxy, phenyl, phenyl-(C1-C6)alkyl, phenyl-(C1-C6)alkoxy, phenoxy, phenoxy-(C1-C6)alkyl, phenoxy-(C1-C6)alkoxy, phenylthio, phenyl-S(O)p—(C1-C6)alkyl, phenyl-S(O)p—(C1-C6)alkoxy, where p in each case independently of one another is 0, 1 or 2, phenylamino, phenylamino-(C1-C6)alkyl, phenylamino-(C1-C6)alkoxy or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle optionally bonded via an alkylene group or an alkoxy group, containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where each of the specified cyclic radicals Raain the cyclic moiety is optionally substituted by one or more identical or different radicals selected from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy.

8. The compound of formula (I) and/or salt thereof as claimed in claim 1, wherein

(R2)nrepresents n substituents R2,

where R2(if n=1) or each of the substituents R2(if n is greater than 1) independently of the others represents halogen, cyano, nitro, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)alkylthio, (C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy, (C1-C6)haloalkylthio, (C1-C6)haloalkylsulfinyl, (C1-C6)haloalkylsulfonyl, (C2-C6)alkenyl, (C2-C6)alkynyl, tri[(C1-C4)alkyl]silyl or tri[(C1-C4)alkyl]silyl-(C1-C4)alkyl,

and/or

(R3)mrepresents m substituents R3,

where R3(if m=1) or each of the substituents R3(if m is greater than 1) independently of one another represents halogen, cyano, nitro, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)alkylthio, (C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl, (C1-C6)haloalkyl, (C2-C6)haloalkenyl, (C1-C6)haloalkoxy, (C1-C6)haloalkylthio, (C1-C6)haloalkylsulfinyl, (C1-C6)haloalkylsulfonyl, (C2-C6)alkenyl, (C2-C6)alkynyl, NR*R**, tri[(C1-C4)alkyl]silyl or tri[(C1-C4)alkyl]silyl(C1-C4)alkyl

or where in each case two groups R3directly adjacent on the ring together represent a group of the formula —Z3-A**-Z4—, in which

A** represents an alkylene group having 1 to 4 carbon atoms which is optionally substituted by one or more radicals from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy,

Z3represents a direct bond, O or S and

Z4represents a direct bond, O or S,

where the group —Z3-A**-Z4together with the carbon atoms, bonded to the group, of the phenyl ring form a fused-on 5- or 6-membered ring,

R*, R** each independently of one another or together with the nitrogen atom have the meaning mentioned above and

n, m in each case independently of one another represent 0, 1, 2, 3, 4 or 5, optionally 0, 1, 2 or 3, optionally 0, 1 or 2.

9. The compound of formula (I) and/or salt thereof as claimed in claim 1, wherein

(R2)nrepresents n substituents R2, where, in the case that n=1, the substituent R2or, in the case that n is greater than 1, each of the substituents R2independently of the others represents

halogen, cyano, nitro, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)alkylsulfinyl, (C1-C4)alkylsulfonyl, (C1-C4)haloalkyl, (C2-C4)haloalkenyl, (C1-C4)haloalkoxy, (C1-C4)haloalkylthio, (C1-C4)haloalkylsulfinyl, (C1-C4)haloalkylsulfonyl, (C2-C4)alkenyl, (C2-C4)alkynyl, tri[(C1-C4)alkyl]silyl or tri[(C1-C4)alkyl]silyl(C1-C4)alkyl, and

n represents 0, 1, 2, 3, or 4, optionally 0, 1, 2 or 3, optionally in particular 0, 1 or 2.

10. The compound of formula (I) and/or salt thereof as claimed in claim 1, wherein

(R3)mrepresents m substituents R3,

where in the case that m=1, the substituent R3or, in the case that m is greater than 1, each of the substituents R3independently of one another represents halogen, cyano, nitro, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)alkylsulfinyl, (C1-C4)alkylsulfonyl, (C1-C4)haloalkyl, (C2-C4)haloalkenyl, (C1-C4)haloalkoxy, (C1-C4)haloalkylthio, (C1-C4)haloalkylsulfinyl, (C1-C4)haloalkylsulfonyl, (C2-C6)alkenyl, (C2-C6)alkynyl or tri[(C1-C4)alkyl]silyl-Zb—, where Zb=is a covalent bond or (C1-C4)alkylene, or

in each case two groups R3directly adjacent to one another at the ring together represent a group of the formula —Z3-A**-Z4—,

where

A** represents an alkylene group which is optionally substituted by one or more radicals from the group halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy,

Z3represents O or S and

Z4represents O or S,

where the group —Z3-A**-Z4— together with the carbon atoms, attached to the group, of the phenyl ring form a fused-on 5- or 6-membered ring,

m represents 0, 1, 2, 3, 4 or 5, optionally 0, 1, 2, 3 or 4, optionally 0, 1, 2 or 3.

11. The compound of formula (I) and/or salt thereof as claimed in claim 1, wherein

(R2)nrepresents n substituents R2,

where, in the case that n=1, the substituent R2or, in the case that n is greater than 1, each of the substituents R2independently of one another represents fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethyl, trifluoromethoxy, trifluoroalkylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, and

(R3)mrepresents m substituents R3,

where, in the case that m=1, the substituent R3or, in the case that m is greater than 1, each of the substituents R3independently of the others represents fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethyl, trifluoromethoxy, trifluoroalkylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, and

m represents 0, 1, 2, 3 or 4, optionally 0, 1, 2 or 3, and

n represents 0, 1, 2 or 3, optionally 0, 1 or 2.

12. A product comprising a compound of formula (I) and/or salt thereof as defined in claim 1,

that is a herbicide and/or plant growth regulator, optionally for crops of useful plants and/or ornamental plants.

13. A herbicidal or plant growth-regulating composition, wherein the composition comprises one or more compounds of the formula (I) and/or salts thereof as defined in claim 1,

and one or more further substances selected from groups (i) and/or (ii):

(i) one or more further agrochemically active substances, optionally selected from the group consisting of insecticides, acaricides, nematicides, further herbicides, fungicides, safeners, fertilizers and/or further growth regulators,

(ii) one or more formulation auxiliaries customary in crop protection.

14. A method for controlling one or more harmful plants or for regulating the growth of plants, comprising applying an effective amount

of one or more compounds of the formula (I) and/or salts thereof, as defined in claim 1,

of a composition as claimed in claim 13,

to the plants, seeds of plants, the soil in which or on which the plants grow or an area under cultivation.

15. A process for preparing a compound of formula (I) or salt as defined in claim 1, comprising converting a compound of formula (E)

by reduction into a compound of the formula (Ia)

and the compound (Ia) is optionally reacted further to give a compound of the formula (I), provided R1in formula (I) does not represent hydrogen, where

R represents hydrogen or an organic radical, optionally a radical selected from the group of the radicals defined for R1.



Получить PDF