Method for Producing 4-Aminobut-2-Enolides

Process for preparing 2,2-difluoroethylamine derivatives, wherein compounds of the general formula (IV) are reduced to the corresponding 2,2-difluoroethylamine derivatives of the general formula (III), where the A radical is as defined in the description: ...

Process for the preparation of 5-fluoro-1H-pyrazoles starting from hexafluoropropene

A new process for the preparation of 5-fluoro-1H-pyrazoles of the general formula (I) as described herein and further reactions with this compound.

3-thiocarbamoylpyrazole derivatives as pesticides

Phenyl-substituted cyclic ketoenols

The present invention relates to new compounds of the formula (I) in which X, Y and Z have the meanings given in the description and Het represents one of the groups in which A, B, D and G have the meanings given in the description, a plurality of processes for their preparation, and to their use as pesticides and herbicides.

Process for preparing quinolone- and naphthyridone- carboxylic acids and esters thereof

An improved process for preparing quinolone- and naphthyridonecarboxylic acids and esters thereof from benzoyl chlorides and nicotinoyl chlorides, respectively, in which the reaction carried out in the presence of a non-polar to slightly polar solvent without separation of intermediaries that form during the process.

PROCESS FOR PREPARING TETRAZOLE-SUBSTITUTED ANTHRANILAMIDE DERIVATIVES AND NOVEL CRYSTAL POLYMORPHS OF THESE DERIVATIVES

The present invention relates to a process for preparing tetrazole-substituted anthranilamide derivatives of the formula (I) 2. Process for preparing a compound of formula (I) according to claim 1 , where{'sup': 1', '3, 'sub': 1', '5, 'R, Rare each independently (C-C)-alkyl,'}{'sup': '2', 'sub': 1', '6, 'Ris halogen or C-C-alkyl,'}{'sup': '4', 'Ris hydrogen, chlorine or cyano,'}{'sup': '5', 'sub': 1', '3, 'Ris (C-C)perfluoroalkyl,'}Z is N.3. Process for preparing a compound according to claim 1 , where{'sup': 1', '3, 'R, Rare each independently methyl, ethyl or tert-butyl,'}{'sup': '2', 'Ris fluorine or chlorine,'}{'sup': '4', 'Ris chlorine or cyano,'}{'sup': '5', 'sub': 3', '2', '5, 'Ris CFor CF,'}Z is N.4. Process for preparing a compound according to claim 1 , wherein Ris CF.5. Process for preparing a compound according to claim 1 , wherein Ris chlorine claim 1 , Ris methyl and Ris cyano.9. Crystal polymorph B according to claim 7 , wherein the x-ray powder diffractogram thereof using Cu Kα radiation corresponds essentially to the spectrum reproduced in FIG.11. Crystal polymorph B according to claim 7 , having a Raman spectrum that corresponds essentially to the spectrum reproduced in .12. Agrochemical composition comprising the compound of the formula (I-1) of crystal polymorph B according to .13. A compound of the formula (I-1) of crystal polymorph B according to suitable for production of an insecticidally active composition.14. Method for controlling unwanted insects claim 7 , comprising applying an agrochemical composition comprising the compound of the formula (I-1) of crystal polymorph B according to to insects and/or their habitat and/or seed.16. Agrochemical composition comprising the compound of the formula (I-1) of crystal polymorph B according to .17. Agrochemical composition comprising the compound of the formula (I-1) of crystal polymorph B according to .18. Method for controlling unwanted insects claim 8 , comprising applying an agrochemical ...

Process for preparing 5-fluoro-1-alkyl-3-fluoroalkyl-1H-pyrazole-4-carbaldehyde

A method for the preparation of compounds of formula (I), for example, N-methyl-3-difluoromethyl-5-fluorpyrazole aldehyde, starting from compounds of formula (II), for example, N-methyl-3-haloalkyl-5 chloropyrazole aldehyde, comprising simultaneous fluorination (one step process) of haloalkyl group in position 3 and replacing haloatom in position 5 by fluorine.

Method for the production of 2-amino-5-cyano-N,3-dimethylbenzamide

The present invention relates to a process for preparing 2-amino-5-cyano-N,3-dimethylbenzamide of formula (I) by reacting 2-amino-5-cyano-3-methylbenzoic esters or diesters with methylamine.

Process For Preparing Fluoroalkyl Nitriles

The present invention relates to a process for preparing fluoroalkyl nitriles by reacting fluorinated carboxamides with halides and fluorinated carboxylic acids.

Method for producing alkenylnitrobenzene derivatives unbranched in the 1-position

The present invention relates to a process for preparing alkenylnitrobenzenes and alkylanilines, which are of significance as intermediates for fungicidally active alkylanilides.

Process for preparing pyridyl-substituted pyrazoles

The present invention relates to a process for preparing 1-pyridyl-substituted pyrazoles, comprising the reaction of acetyleneketones with pyridylhydrazine derivatives to give 1-pyridyl-substituted dihydro-1H-pyrazoles, the further reaction thereof with elimination of water to give 1-pyridyl-substituted trihalomethylpyrazoles, and the further processing thereof.

Method for producing enaminocarbonyl compounds

The present invention relates to a process for the preparation of enaminocarbonyl compounds of the formula (I) where compounds of the formula (II) are reacted in the presence of a Brønsted acid to give compounds of the formula (I), and A, R1 and Z are as defined in the description, and also corresponding starting compounds which are used in the process according to the invention.

PROCESS FOR PREPARING CYANIMINO-1,3-THIAZOLIDINES

The present invention relates to a process for preparing cyanimino-1,3-thiazolidines, which are important building blocks for the preparation of crop protection active ingredients and pharmaceuticals, by the following scheme: where A is an alkali metal and X represents an acid radical.

process for preparing 5-fluoroolefins 1-alkyl-3 it fluoroalkyl it 1h-pyrazole it 4 it carbaldehyde

Method for producing substituted anthranilic acid derivatives

The present invention relates to a process for preparing substituted anthranilic acid derivatives of the formula (I) in which R1, R2, R3and R4are each as defined in the description, by conversion of compounds of the general formula (IV) in the presence of a palladium catalyst and carbon monoxide. The present invention likewise relates to compounds of the general formula (IV).

PROCESS FOR PREPARING SODIUM SALTS OR POTASSIUM SALTS OF 4-HYDROXY-2-OXO-2,5-DIHYDROFURAN-3-CARBOXYLATE

Process for preparing sodium or potassium salts of 4-hydroxy-2-oxo-2,5-dihydrofuran-3-carboxylic esters, comprising the reaction of a malonic ester with potassium hydroxide to give the corresponding malonic ester potassium salt of the formula (III) 2. The process according to claim 1 , in which an aqueous potassium hydroxide solution is used in (i) claim 1 , and in which the solvent in (i) is an alcohol.3. The process according to claim 1 , in which claim 1 , on completion of conversion in (i) claim 1 , the malonic ester potassium salt of formula (III) is separated from unconverted malonic ester of formula (II) by phase separation before said malonic ester potassium salt is used in (ii).4. The process according to claim 1 , in which claim 1 , in (ii) claim 1 , from 0.8 to 5.0% by weight of water is added again to the reaction mixture after performance of an azeotropic dewatering.5. The process according to claim 4 , in which (ii) is performed in substance.6. The process according to claim 1 , in which claim 1 , in (iii) claim 1 , sodium methoxide claim 1 , sodium ethoxide claim 1 , potassium methoxide or potassium ethoxide is used.7. The process according to claim 6 , in which the sodium methoxide or the potassium methoxide is present dissolved in methanol claim 6 , and the sodium ethoxide or the potassium ethoxide is present dissolved in ethanol. The present invention relates to a process for preparing sodium or potassium salts of 4-hydroxy-2-oxo-2,5-dihydrofuran-3-carboxylic esters proceeding from malonic esters.The preparation of hydroxy-2-oxo-2,5-dihydrofuran-3-carboxylic esters, the corresponding tautomers or the alkali metal salts thereof, and also the use thereof as a component in the synthesis of biologically active compounds, is known (WO 2011/018180, WO 2009/036899, J. Chem. Soc., Perkin Trans. 1, 1985, pages 1567 to 1576, Berichte der Deutschen Chemischen Gesellschaft (1911), 44, 1759-1765). However, the known processes have disadvantages as described ...

Aryl-substituted pyrazoles

The present invention relates to a process for preparing 1-aryl-substituted pyrazoles, comprising the reaction of alkoxy enones and enamino ketones with arylhydrazine derivatives to give 1-aryl-substituted dihydro-1H-pyrazoles, the further reaction thereof with elimination of water to give 1-aryl-substituted trihalomethylpyrazoles, and the further processing thereof.

Preparing 5-Fluoro-1-alkyl-3-fluoroalkyl-1H-pyrazole-4-carbaldehydes

The present invention relates to a novel process for preparing 5-fluoro-1-alkyl-3-fluoro-1-alkyl-1H-pyrazole-4-carbonyl chlorides, a useful intermediate in the manufacture of fungicides. 14-. (canceled)6. The compound of formula (IV) according to where Rrepresents methyl claim 5 , ethyl claim 5 , n-propyl claim 5 , isopropyl claim 5 , butyl claim 5 , pentyl and Rrepresents CFH claim 5 , CF claim 5 , CFCl claim 5 , CCF claim 5 , CF claim 5 , or CF.7. The compound of formula (IV) according to claim 5 , where Rrepresents methyl and Rrepresents CFH or CF.8. 5-Fluoro-1-methyl-3-difluoromethyl-1H-pyrazole-4-carbaldehyde.10. (canceled) The present application claims priority to U.S. Provisional Patent Application No. 61/262,641, filed Nov. 19, 2009, which is hereby incorporated by reference in its entirety.The present invention relates to a novel process for preparing 5-fluoro-1-alkyl-3-fluoroalkyl-1H-pyrazole-4-carbonyl chlorides, a useful intermediate in the manufacture of fungicides.Pyrazolecarbonyl chlorides are important synthons for preparing crop protection actives. Pyrazolecarbonyl chlorides are typically prepared by reacting carboxylic acids with a chlorinating agent. One advantage of this method is that appropriate carboxylic acids are easy to obtain and hence available on an industrial scale. This prerequisite is not satisfied in the case of the preparation of substituted pyrazolecarbonyl chlorides, since the corresponding carboxylic acids are not readily available.It has now been found that 5-fluoro-1-alkyl-2-fluoroalkyl-1H-pyrazole-4-carbonyl chlorides of formula (I)where Rrepresents C-C-alkyl and Rrepresents C-C-fluoroalkyl, are obtained when 5-chloro-1-alkyl-3-fluoroalkyl-1H-pyrazole-4-carbaldehyde of formula (II)where Rand Rare each as defined above, is initially reacted (step 1) with a fluorinating agent of formula (III)MF  (III)where M represents Li, Na, K, Cs, AlkN (where Alk represents C-C-alkyl),and optionally in the presence of a phase transfer ...

Dioxolane and dioxane derivatives and a process for their preparation

The present invention relates to novel acylmethylene-1,3-dioxolanes and acylmethylene-1,4-dioxanes of the general formula (I) in which R1, R2, R3 and n have the meanings given in the description, and also a novel process for their preparation. Acylmethylene-1,3-dioxolanes and acylmethylene-1,4-dioxanes are important intermediates for the preparation of pyrazoles and anthranilamides, which can be used as insecticides.

Process for preparing aryl-substituted pyrazoles

The present invention relates to a process for preparing 1-aryl-substituted pyrazoles, comprising the reaction of alkoxy enones and enamino ketones with arylhydrazine derivatives to give 1-aryl-substituted dihydro-1H-pyrazoles, the further reaction thereof with elimination of water to give 1-aryl-substituted trihalomethylpyrazoles, and the further processing thereof.

Alkoxy enones and enamino ketones and a process for preparation thereof

The present invention relates to novel alkoxy enones and enamino ketones, and to a novel process for preparation thereof. Alkoxy enones and enamino ketones are valuable intermediates for preparation of pyrazoles and anthranilamides, which can be used as insecticides.

METHOD FOR THE PRODUCTION OF 2-AMINO-5-CYANO-N,3-DIMETHYLBENZAMIDE

The present invention relates to a process for preparing 2-amino-5-cyano-N,3-dimethylbenzamide of formula (1) 2. The process according to claim 1 , wherein a 2-amino-5-cyano-3-methylbenzoic ester of formula (II) and/or a 2-amino-5-cyano-3-methylbenzoic diester of formula (III) is reacted with MeNHby using at least one base.3. The process according to claim 1 , wherein a compound of formula (I) is obtained by reacting a 2-amino-5-cyano-3-methylbenzoic ester of formula (II).4. The process according to claim 1 , wherein a compound of formula (I) is obtained by reacting a 2-amino-5-cyano-3-methylbenzoic diester of formula (III).5. The process according to claim 2 , and wherein the base is selected from the group consisting of sodium amide claim 2 , sodium hydride claim 2 , sodium hydroxide claim 2 , sodium cyanide claim 2 , potassium cyanide claim 2 , potassium carbonate claim 2 , sodium carbonate claim 2 , caesium carbonate claim 2 , sodium methoxide and triethylamine8. The process according to claim 6 , wherein from 0.8 mol to 1.4 mol of copper(I) cyanide is used per 1 mol of compound of formula (IV) or (V).9. The process according to claim 6 , wherein copper(I) cyanide is used in N claim 6 ,N-dimethylformamide claim 6 , N claim 6 ,N-dimethylacetamide claim 6 , N-methylformanilide claim 6 , N-methylpyrrolidone claim 6 , hexamethylphosphoramide or dimethyl sulphoxide as solvent. The present invention relates to a process for preparing 2-amino-5-cyano-N,3-dimethylbenzamide of formula (I)by reacting 2-amino-5-cyano-3-methylbenzoic esters or diesters with methylamine, for which the 2-amino-5-cyano-3-methylbenzoic esters or diesters are obtainable from the corresponding bromine compounds by cyanation with copper(I) cyanide. The bromine compounds are simple to prepare by brominating with a mixture of hydrogen bromide/hydrogen peroxide.Preparation processes that also encompass the compound of formula (I) are already described in the literature (cf. for example WO 2008/08252, ...

Process for preparing 2,4-dioxotetrahydrofuran-3-carboxylates

Process for preparing 2,4-dioxotetrahydrofuran-3-carboxylates of the formula (I) and/or (I′) comprising the reaction of a haloacetyl chloride compound of the formula (II) with a malonic ester of the formula (III) in which Hal, R1 and R2 have the definitions stated in the application, in the presence of a suitable base and optionally in the presence of a solvent; the addition of a sufficient amount of water to the reaction mixture; and the isolation of the desired 2,4-dioxotetrahydrofuran-3-carboxylate.

Novel alkoxy enones and enamino ketones and a process for preparation thereof

The present invention relates to novel alkoxy enones and enamino ketones, and to a novel process for preparation thereof. Alkoxy enones and enamino ketones are valuable intermediates for preparation of pyrazoles and anthranilamides, which can be used as insecticides.

Process for preparing 2,2-difluoroethylamine

The present invention relates to a process for preparing 2,2-difluoroethylamine proceeding from 2,2-difluoro-1-haloethane using ammonia in a solvent which has a maximum water content of 15% by volume and in the presence of a catalyst which accelerates the reaction with ammonia.

Process for preparing 3,5-bis(fluoroalkyl)pyrazole derivatives from α,α-dihaloamines

The present invention relates to a novel process for preparing 3,5-bis(fluoroalkyl)pyrazole derivatives from α,α-dihaloamines.

Method for the regioselective synthesis of 1-Alkyl-3-haloalkyl-pyrazole-4-carboxylic acid derivatives

The present invention relates to a process for the regioselective synthesis of 1-alkyl-3-halo-alkylpyrazole-4-carboxylic acid derivatives by cyclization of 2,3-disubstituted acrylic acid derivatives, and to the hydrazones formed as intermediates in the process.

METHOD FOR PRODUCING 2-CHLOROALLYL THIOCYANATE AND 2-CHLOROALLYL ISOTHIOCYANATE

A process is described for producing 2-chloroallyl isothiocyanate from 2,3-dichloro-1-propene by reacting the 2,3-dichloro-1-propene with a thiocyanate in the presence of a phase transfer catalyst, without diluent or in the presence of up to 15 percent by weight based on 2,3-dichloropropene and simultaneously in the presence of an excess of from 10 to 200 mol percent of 2,3-dichloro-1-propene based on the thiocyanate. A process starting from 1,2,3-trichloropropane is also described. 2. The process according to claim 1 , wherein the amount used of a diluent is up to 10 percent by weight claim 1 , based on the 2 claim 1 ,3-dichloropropene of formula (III).3. The process according to claim 1 , where the amount used of a diluent is up to 5 percent by weight claim 1 , based on the 2 claim 1 ,3-dichloropropene of formula (III).4. The process according to any of claim 1 , where said reacting proceeds at a temperature range from 50 to 100° C. The present invention relates to a process for producing 2-chloroallyl thiocyanate of the formula (I) and 2-chloroallyl isothiocyanate of the formula (II).2-Chloroallyl thiocyanate of the formula (I) is a known compound (see by way of example EP 0761649). It is also known that 2-chloroallyl thiocyanate of the formula (I) can be produced by reacting, in a diluent, a 2,3-dihalo-1-propene, preferably 2,3-dichloro-1-propene of the formula (III)with a thiocyanate of the general formula (IV)M(SCN)  (IV),in whichAn example of a suitable diluent described for the known processes is acetonitrile (EP 446913; CN 1401646) or toluene, optionally with addition of a phase transfer catalyst (Shanghai Huagong 27 (2002) 25-27; J. Agric. Food Chem. 56 (2008) 10805-10810). However, the use of these diluents is disadvantageous for an industrial process. By way of example, the dilution of the starting materials can markedly reduce the reaction rate and thus prolong the reaction time required. The use of a diluent also unavoidably implies additional work-up ...

FUNGICIDE PYRAZOLE CARBOXAMIDES DERIVATES

The present invention relates to pyrazole carboxamides derivatives of formula (1) wherein Y represents CRor N, T represents S or O, X1 and X2 represent a chlorine or a fluorine atom, and Z1 represents a substituted or non-substituted cyclopropyl; Their process of preparation, their use as fungicide, and/or anti-mycotoxin active agents, and/or insecticide, and/or nematicide, particularly in the form of fungicide compositions, and methods for the control of phytopathogenic fungi, notably of plants, using these compounds or compositions. 2. A compound according to wherein Y represents CR.3. A compound according to wherein Y represents N.4. compound according to wherein T represents O.5. A compound according to wherein Xrepresents a fluorine atom.6. A compound according to wherein Xrepresents a fluorine atom.7. A compound according to wherein Zrepresents a non substituted cyclopropyl.8. A compound according to wherein Zand Zindependently represent a hydrogen atom or a methyl.9. A compound according to wherein Zrepresents a hydrogen atom and Zrepresents a hydrogen atom or a methyl.10. A compound according to wherein R claim 1 , R claim 1 , R claim 1 , Rand R claim 1 , which can be the same or different claim 1 , represent a hydrogen atom; a halogen atom; substituted or non substituted C-C-alkyl; C-C-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C-C-cycloalkyl; tri(C-C-alkyl)silyl; or substituted or non substituted C-C-alkylsulfanyl.11. A compound according to wherein the substituent Rrepresents a halogen atom; C-C-alkyl; C-C-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C-C-cycloalkyl; tri(C-C-alkyl)silyl or C-C-halogenoalkylsulfanyl comprising up to 9 halogen atoms which can be the same or different.12. A compound according to wherein the substitutents Rand R claim 1 , which can be the same or different claim 1 , represent a halogen atom; C-C-alkyl; C-C-halogenoalkyl ...

process for preparing derivatives of anthranilic acid diamide substituted tetrazole by reacting with esters antranílicos pyrazoles acids

Preparing 5-fluoro-1-alkyl-3-fluoroalkyl-1H-pyrazole-4-carbonyl chlorides

The present invention relates to a novel process for preparing 5-fluoro-1-alkyl-3-fluoroalkyl-1H-pyrazole-4-carbonyl chlorides, a useful intermediate in the manufacture of fungicides.

Process for Preparing 1-Alkyl-3-difluoromethyl-5-hydroxypyrazoles

The present invention relates to a process for preparing 1-alkyl-3-difluoromethyl-5-hydroxypyrazoles, which are valuable intermediates for the production of fungicides.

Use of substituted aryl imidazoles

Method for producing 2,2-difluoroethylamine derivatives by imine hydrogenation

Process for preparing 2,2-difluoroethylamine derivatives, wherein compounds of the general formula (IV) are hydrogenated to the corresponding 2,2-difluoroethylamine derivatives of the general formula (III), where the A radical is as defined in the description:

PROCESS FOR THE PREPARATION OF 5-SUBSTITUTED 1-ALKYLTETRAZOLYL OXIME DERIVATIVES

The present invention relates to a process for the preparation of 5-substituted 1-alkyltetrazolyl oxime derivatives. 3. Process according to one of claim 1 , characterized in that step (1) is carried out in the presence of a base.4. Process according to claim 3 , characterized in the molar ratio of base to the oxime of the formula (II) used is 0.8-10.5. Process according to claim 1 , characterized in that step (1) is carried out in a solvent.6. Process according to claim 1 , characterized in that step (2) is carried out in the presence of a base.7. Process according to claim 6 , characterized in that the molar ratio of base to the compound of the formula (IV) used is 0.8-10. The present invention relates to a process for the preparation of 5-substituted 1-alkyltetrazolyl oxime derivatives.5-Substituted 1-alkyltetrazolyl oxime derivatives are important intermediate compounds in active ingredient manufacture or are already fungicidally effective compounds (see e.g. WO 2010/000841). It is already known that 5-substituted 1-alkyltetrazoles can be prepared by lithiation of 1-methyltetrazole at −70° C. (cf. 1971, 49, 2139-2142). However, the yield using the example of 5-benzoyl-1-methyltetrazole is only 41%. The 1-methyltetrazole used likewise has to be prepared in a multistage synthesis sequence. For an industrial reaction, the low temperatures and the expensive use of butyllithium are disadvantageous. Another process for the preparation of 5-benzoyl-1-methyltetrazole is known from 1963, 85, 2967-2976. Benzyl cyanide is reacted with ammonium azide to give 5-benzyltetrazole and then oxidized with chromium trioxide to give 5-benzoyltetrazole. The methylation to 5-benzoyl-1-methyltetrazole takes place with diazomethane. This synthesis route is likewise disadvantageous as regards safety and economical aspects. The preparation of 1-cyclohexyl-5-acetyltetrazole by reacting acetyl chloride over cyclohexyl isocyanide with subsequent reaction with hydrazoic acid is also known (cf ...

Process for the preparation of 1-alkyl and 1-aryl-5-pyrazolecarboxylic acid derivatives

The present invention relates to a process for the preparation of 1-alkyl- or 1-aryl-substituted 5-pyrazolecarboxylic acid derivatives comprising the reaction of substituted 1,3-dioxolanes and 1,4-dioxanes with alkyl- or arylhydrazines to give 1-alkyl- or 1-aryl-substituted dihydro-1H-pyrazoles, and their further reaction to give 1-alkyl- or 1-aryl-substituted 5-pyrazolecarboxylic acid derivatives, which can be used as valuable intermediates for producing insecticidally effective anthranilamides.

Novel alkoxy enones and enamino ketones and a process for preparation thereof

The present invention relates to novel alkoxy enones and enamino ketones, and to a novel process for preparation thereof. Alkoxy enones and enamino ketones are valuable intermediates for preparation of pyrazoles and anthranilamides, which can be used as insecticides. 3. A compound of formula (I) according to claim 2 ,wherein{'sup': '4', 'sub': 1', '6', '1', '6', '1', '6', '2', '1', '6', '2', '1', '6', '2, 'Ris —(C═O)(C-C)alkyl, (C═O)halo(C-C)alkyl, —(C═O)O—(C-C)alkyl, SO(C-C)alkyl, SO-halo(C-C)alkyl, SO-aryl,'}X is fluorine, chlorine or bromine, and{'sup': '5', 'Ris alkoxy.'}4. A compound of formula (I) according to claim 3 ,wherein{'sup': '4', 'sub': 1', '6, 'Ris —(C═O)(C-C)alkyl,'}X is chlorine or bromine, and{'sup': '5', 'sub': 1', '6, 'Ris (C-C)alkoxy.'}5. The process according to wherein the reaction is effected in the presence of an acid.6. The process according to wherein the acid is selected from the group consisting of HCl claim 5 , HSO claim 5 , CHCOOH and CFCOOH.7. The process according to wherein the reaction is effected in the presence of a catalyst.8. The process according to wherein the acid is CHCOOH.9. The process according to wherein the catalyst is tetrabutylammonium bromide.10. The process according to wherein the reaction is effected in the presence of an acid wherein said acid is selected from the group consisting of HCl claim 1 , H2SO4 claim 1 , CH3COOH and CFCOOH. This application is a continuation-in-part of application Ser. No. 12/842,249, filed Jul. 23, 2010, now pending. The patent application identified above is incorporated here by reference in its entirety to provide continuity of disclosure.The present invention relates to novel alkoxy enones and enamino ketones, and to a novel process for preparation thereof. Alkoxy enones and enamino ketones are valuable intermediates for preparation of pyrazoles and anthranilamides, which can be used as insecticides.The literature discloses that 5-bromo-1,1,1-trihalo-4-methoxypent-3-en-2-one has ...

Process for the preparation of 5-substituted 1-alkyltetrazolyl oxime derivatives

The present invention relates to a process for the preparation of 5-substituted 1-alkyltetrazolyl oxime derivatives.

Process for preparing 3,5-bis(haloalkyl)pyrazole derivatives from α,α-dihaloamines and ketimines

The present invention relates to a novel process for preparing 3,5-bis(haloalkyl)pyrazole derivatives from α,α-dihaloamines and ketimines.

Process for the preparation of 2,2-difluoroethylamine derivatives starting from N-(2,2-difluoroethyl)prop-2-en-1-amine

Process for the preparation of 2,2-difluoroethylamine derivatives of the formula (IV) comprising the steps (i) and (ii): step (i): reaction of N-(2,2-difluoroethyl)prop-2-en-1-amine of the formula (I) with a compound of the formula (II) A-CH 2 -E  (II) to give a compound of the formula (III) optionally in the presence of an inorganic or organic base, and step (ii): removal of the allyl group from the compound of the formula (III), in which, in the formulae (II), (III) and (IV), A and E have the meanings given in the description.

CATALYTIC GAS PHASE FLUORINATION OF 1,1,2-TRICHLOROETHANE AND/OR 1,2-DICHLOROETHENE TO PRODUCE 1-CHLORO-2,2-DIFLUOROETHANE

The invention is directed to a catalyst for the gas phase fluorination of 1,1,2-trichloroethane and/or 1,2-dichloroethene with HF to give 1-chloro-2,2-difluoroethane which catalyst is prepared by co-depositing FeCland MgClon chromia-alumina, or co-depositing Cr(NO)and Ni(NO)on active carbon, or by doping alumina with ZnCl, and to a process for the preparation of 1-chloro-2,2-difluoroethane comprising a catalytic gas phase fluorination of 1,1,2-trichloroethane and/or 1,2-dichloroethene wherein one of the catalysts according to claim 2 or 3 is used. 1. A catalyst for gas phase fluorination of 1 ,1 ,2-trichloroethane and 1 ,2-dichloroethene with HF to give 1-chloro-2 ,2-difluoroethane which is prepared by co-depositing FeCland MgClon chromia-alumina , or co-depositing Cr(NO)and Ni(NO)on active carbon , or by doping alumina with ZnCl.2. The catalyst according to which has been fluorinated by treating the catalyst with a fluorine containing activation agent at a temperature not exceeding 400° C.3. The fluorinated catalyst according to which has been fluorinated by HF as activation agent.4. A process for preparation of 1-chloro-2 claim 2 ,2-difluoroethane comprising a catalytic gas phase fluorination of 1 claim 2 ,1 claim 2 ,2-trichloroethane comprising using a catalyst according to .5. The process according to claim 4 , wherein the ratio of catalyst weight to and flow rates of 1 claim 4 ,1 claim 4 ,2-trichloroethane and HF is in a range of 100 to 300.6. A process for preparation of 1-chloro-2 claim 2 ,2-difluoroethane comprising a catalytic gas phase fluorination of 1 claim 2 ,2-dichloroethene comprising using a catalyst according to .7. The process according to claim 6 , wherein the ratio of catalyst weight to flow rates of 1 claim 6 ,1 claim 6 ,2-trichloroethane and HF is in the range of 250 to 500.8. A process for preparation of 1-chloro-2 claim 2 ,2-difluoroethane comprising a catalytic gas phase fluorination of 1 claim 2 ,1 claim 2 ,2-trichloroethane and 1 claim 2 , ...

Process for preparing 2,4-dihydroxyphenyl 4-methoxybenzyl ketones

The invention relates to a process for preparing 2,4-dihydroxyphenyl 4-methoxybenzyl ketones of the formula (I) by Friedel-Crafts acylation in hydrogen fluoride (HF). 2,4-Dihydroxyphenyl 4-methoxybenzyl ketones of the formula (I) in which R1 and R2 are each hydrogen, chlorine, fluorine, bromine, iodine, CF3, methyl, optionally substituted alkoxy, OCF3, C(CH3)3, CH2(CH3)2, CH(CH3)2, R3 is hydrogen, Cl, F, Br, optionally substituted alkyl, optionally substituted alkoxy, C(CH3)3, and X is hydroxyl, F, Cl, Br, optionally substituted alkoxy, are obtained in high yield and high purity by reacting phenylacetic acid derivatives of the formula (II) with phenols of the formula (III) in liquid hydrogen fluoride (HF).

Method for preparing 1-alkyl-3-difluoromethyl-5-fluor-1H-pyrazole-4-carbaldehydes and 1-alkyl-3-difluoromethyl-5-fluor-1H-pyrazole-4-carboxylates

The present invention relates to a novel method for preparing 1-alkyl-3-difluoromethyl-5-fluor-1H-pyrazole-4-carbaldehydes or esters thereof of formula (I) by means of reductive dehalogenation, starting from 1-alkyl-3-chlorodifluoromethyl-5-fluoro-1H-pyrazole-4-carbaldehydes or esters thereof Formula (I) ...

METHOD FOR PRODUCING 2,2-DIFLUOROETHYLAMINE DERIVATIVE BY AMIDE HYDROGENATION

Process for preparing 2,2-difluoroethylamine derivatives, wherein compounds of the general formula (IV) are reduced to the corresponding 2,2-difluoroethylamine derivatives of the general formula (III), where the A radical is as defined in the description: ...

Process for preparing tetrazole-substituted anthranilamide derivatives and novel crystal polymorphs of these derivatives

The present invention relates to a process for preparing tetrazole-substituted anthranilamide derivatives of the formula (I) in which R1, R2, R3, R4, R5 and Z are each as defined in the description, and to a novel crystal polymorph of these derivatives and to the use thereof in agrochemical formulations.

process for producing 2.2 it difluoroetilamina and their salts from difluoroacetonitrila

3-triazolylphenyl-substituted sulphide derivatives as acaricides and insecticides

The present invention constitutes new 3-triazolylphenyl-substituted sulphide derivatives of the formula (I) in which A1, A2, B0, B1, B2, B3, X, R1, R2 and n are as defined in the description, to their use as acaricides and insecticides for controlling animal pests, and to processes for preparing them.

Method for producing 2,2-difluoroethylamine derivative by amide hydrogenation

Process for preparing 2,2-difluoroethylamine derivatives, wherein compounds of the general formula (IV) are reduced to the corresponding 2,2-difluoroethylamine derivatives of the general formula (III), where the A radical is as defined in the description:

Process for preparing substituted phenylisoxazoline derivatives

The present invention relates to a process for preparing substituted phenylisoxazoline derivatives.

METHOD FOR PRODUCING 2,2 DIFLUOROETHYLAMINE DERIVATIVES BY IMINE HYDROGENATION

Process for preparing 2,2-difluoroethylamine derivatives, wherein compounds of the general formula (IV) are hydrogenated to the corresponding 2,2-difluoroethylamine derivatives of the general formula (III), where the A, R 1 and R 2 radicals are each as defined in the description:

3-[1-(3-haloalkyl)triazolyl]phenyl sulphide derivatives as acaricides and insecticides

The present invention constitutes new 3-[1-(3-haloalkyl)triazolyl]phenyl sulphide derivatives of the formula (I) in which A 1 , A 2 , B 0 , B 1 , B 2 , B 3 , R 1 , R 2 and n are as defined in the description, to their use as acaricides and insecticides for controlling animal pests, and to processes for preparing them.

Process for preparing substituted pyridines

The invention relates to a process for preparing substituted pyridines in a simple and cost-effective manner in good yields by reacting substituted 1,4-dihydropyridines with methyl nitrite in the presence of an acid that contains less than 20% by weight of oxidizing components.

Process for preparing sodium salts or potassium salts of 4-hydroxy-2-oxo-2,5-dihydrofuran-3-carboxylate

Process for preparing sodium or potassium salts of 4-hydroxy-2-oxo-2,5-dihydrofuran-3-carboxylic esters, comprising the reaction of a malonic ester with potassium hydroxide to give the corresponding malonic ester potassium salt of the formula (III) which is then reacted further with a chloroacetic ester to give a compound of the formula (V) followed by a ring closure reaction in which the compound of the formula (V) is reacted with a sodium or potassium alkoxide of the formula ZOR1 where R1, R2, R3 and K are each as defined in the description.

Method for producing tetrazole-substituted anthranilic acid diamide derivatives by reacting pyrazolic acids with anthranilic acid esters

The present invention relates to a process for preparing tetrazole-substituted anthranilic acid diamide derivatives of the formula (I) in which R1, R2, R3, R4, Q and Z have the meanings given in the description, by reacting pyrazole acids with anthranilic esters.

Process for the preparation of 2,2-difluoroethylamine

A process for the preparation of 2,2-difluoroethylamine, comprising the reaction of 2,2-difluoro-1-chloroethane with an imide of the formula (II) in the presence of an acid scavenger, to give a compound of the formula (III) in which, in the compounds of the formulae (II) and (III), R 1 and R 2 are, each independently of one another, hydrogen or C 1 -C 6 -alkyl or R 1 and R 2 form, together with the carbon atoms to which they are bonded, a six-membered aromatic ring which is optionally substituted; and the cleavage of 2,2-difluoroethylamine by reaction of the compound of the formula (III) with acid, base or hydrazine.

Aryl-substituted Pyrazoles

The present invention relates to a process for preparing 1-aryl-substituted pyrazoles, comprising the reaction of alkoxy enones and enamino ketones with arylhydrazine derivatives to give 1-aryl-substituted dihydro-1H-pyrazoles, the further reaction thereof with elimination of water to give 1-aryl-substituted trihalomethylpyrazoles, and the further processing thereof. 3. A compound of the general formula (IV) according to claim 1 , wherein{'sup': '4', 'sub': '3', 'Ris (C═O)CHand X is chlorine.'}4. A compound of the general formula (V) according to claim 2 , wherein{'sup': '4', 'sub': '3', 'Ris (C═O)CHand X is chlorine.'} The present invention relates to a process for preparing 1-(aryl)-substituted pyrazoles, comprising the reaction of alkoxy enones and enamino ketones with hydrazine derivatives to give 1-(aryl)-substituted dihydro-1H-pyrazoles, the further reaction thereof with elimination of water to give 1-(aryl)-substituted trihalomethylpyrazoles, and the further processing thereof.1-(Aryl)-substituted pyrazoles and 1H-pyrazoles are valuable intermediates for preparation of anthranilamides, which can find use as insecticides.The literature has already described the formation of pyrazoles by reaction of 1,3-dicarbonyls or corresponding 1,3-bis-electrophilic reagents with monoalkyl- or monoarylhydrazines (Synthesis 2004, N1. pp 43-52). However, it is reported that, in the case of monoalkyl- or monoarylhydrazines, the result is a mixture of regioisomeric pyrazoles (Tetrahedron 59 (2003), 2197-2205; Martins et al., T. L. 45 (2004) 4935). Attempts to obtain exclusively one regioisomer failed (JOC 2007, 72822 8243-8250). Likewise described in the literature is a process for preparing trifluoromethylpyrazoles (WO 2003/016282). Likewise described are preparation processes for (het)aryl-substituted pyrazoles (WO 2007/144100), wherein the corresponding pyrazoles are obtained by reducing diesters with DIBAL or LiAlH. However, very low temperatures are required, and the use ...

PROCESS FOR PREPARING 5-FLUORO-1-METHYL-3-DIFLUOROMETHYL-1H-PYRAZOLE-4-CARBALDEHYDE

Stereoselective one step fluorination process for the preparation of 2-flouropropionate

The current invention describes a one-step process for the synthesis of 2-fluoropropionates from lactic acid ester derivatives using TFEDMA.

Preparing 5-fluoro-1-alkyl-3-fluoroalkyl-1H-pyrazole-4-carbonyl chlorides

The present invention relates to a novel process for preparing 5-fluoro-1-alkyl-3-fluoroalkyl-1H-pyrazole-4-carbonyl chlorides, a useful intermediate in the manufacture of fungicides.

Method for producing 2,2-difluoroethylamine derivatives by imine hydrogenation

Process for preparing 2,2-difluoroethylamine derivatives, wherein compounds of the general formula (IV) are hydrogenated to the corresponding 2,2-difluoroethylamine derivatives of the general formula (III), where the A, R 1 and R 2 radicals are each as defined in the description:

METHOD FOR PRODUCING SUBSTITUTED PYRAZOLECARBOXYLIC ACID CHLORIDES

The present invention relates to a process for preparing substituted pyrazolyl chlorides by chlorinating aldehydes of the formula (II) under free-radical conditions.

Process for the preparation of fluoroquinolonecarboxylic acids

Fluoroquinolonecarboxylic acids can be prepared by hydrolysis of the corresponding C1-C4-alkyl esters with addition of water, acetic acid, and sulfuric acid using a drastically reduced amount of sulfuric acid if, relative to 1 mol of C1-C4-alkyl fluoroquinolonecarboxylate, less than 30 g of sulfuric acid are employed, the reaction mixture is heated to reflux for 0.5 to 8 hours, then a mixture of acetic acid, C1-C4-alkyl acetate, C1-C4-alkyl alcohol, and optionally water is distilled off, and finally the fluoroquinolonecarboxylic acid prepared is isolated.

Process for preparing aryl-substituted pyrazoles

The present invention relates to a process for preparing 1-aryl-substituted pyrazoles, comprising the reaction of alkoxy enones and enamino ketones with arylhydrazine derivatives to give 1-aryl-substituted dihydro-1H-pyrazoles, the further reaction thereof with elimination of water to give 1-aryl-substituted trihalomethylpyrazoles, and the further processing thereof.

PROCESS FOR PREPARING 2,4-DIHYDROXYPHENYL 4-METHOXYBENZYL KETONES

The invention relates to a process for preparing 2,4-dihydroxyphenyl 4-methoxybenzyl ketones of the formula (I) by Friedel-Crafts acylation in hydrogen fluoride (HF). 2,4-Dihydroxyphenyl 4-methoxybenzyl ketones of the formula (I) in which R1 and R2 are each hydrogen, chlorine, fluorine, bromine, iodine, CF3, methyl, optionally substituted alkoxy, OCF3, C(CH3)3, CH2(CH3)2, CH(CH3)2, R3 is hydrogen, Cl, F, Br, optionally substituted alkyl, optionally substituted alkoxy, C(CH3)3, and X is hydroxyl, F, Cl, Br, optionally substituted alkoxy, are obtained in high yield and high purity by reacting phenylacetic acid derivatives of the formula (II) with phenols of the formula (III) in liquid hydrogen fluoride (HF).

Process for the preparation of 5-fluoro-1H-pyrazoles

A new process for the preparation of 5-fluoro-1H-pyrazoles of the general formula (I) as described herein, resulting from the reaction of an olefin with hydrazine in the presence of water and a base.

Fungicide pyrazole carboxamides derivatives

The present invention relates to pyrazole carboxamides derivatives of formula (1) wherein Y represents CR5or N, T represents S or O, X1 and X2 represent a chlorine or a fluorine atom, and Z1 represents a substituted or non-substituted cyclopropyl; Their process of preparation, their use as fungicide, and/or anti-mycotoxin active agents, and/or insecticide, and/or nematicide, particularly in the form of fungicide compositions, and methods for the control of phytopathogenic fungi, notably of plants, using these compounds or compositions.

Process for preparing 5-fluoro-1-methyl-3-difluoromethyl-1H-pyrazole-4-carbaldehyde

The present invention relates to a novel process for preparing 5-fluoro-1-methyl-3-difluoromethyl-1H-pyrazole-4-carbaldehyde, a useful intermediate in the manufacture of fungicides.

Process for Preparing Pyridyl-Substituted Pyrazoles

The present invention relates to a process for preparing 1-pyridyl-substituted pyrazoles, comprising the reaction of acetyleneketones with pyridylhydrazine derivatives to give 1-pyridyl-substituted dihydro-1H-pyrazoles, the further reaction thereof with elimination of water to give 1-pyridyl-substituted trihalomethylpyrazoles, and the further processing thereof. 2. Process for preparing compounds of the formula (I) according to claim 1 , characterized in that{'sup': '1', 'sub': 1', '6, 'Ris (C-C)-alkoxy, halogen,'}{'sup': '2', 'sub': 1', '6', '1', '6, 'Ris (C-C)alkoxy, aryl(C-C)-alkoxy, fluorine, chlorine, bromine, iodine,'}{'sup': '3', 'sub': 3', '1', '6', '1', '6', '1', '6', '1', '6, 'Ris halogen, CN, NO, (C-C)-alkyl, halo(C-C)-alkyl, (C-C)-alkoxy, halo(C-C)alkoxy.'}3. Process for preparing compounds of the formula (I) claim 1 , characterized in that the preparation of the compound of the formula (V) comprises steps (A) and (B) according to .6. Compounds of the formula (I) according to claim 1 , characterized in that{'sup': '1', 'Ris halogen,'}{'sup': '2', 'Ris fluorine, chlorine, bromine, iodine,'}{'sup': '3', 'sub': '2', 'Ris halogen, CN, NO, alkyl, cycloalkyl, haloalkyl, halocycloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino, cycloalkylamino.'}7. Compounds of the formula (IV) according to claim 1 , characterized in thatX is halogen,{'sup': '3', 'Ris chlorine,'}{'sup': '4', 'Ris benzyl.'}8. Compounds of the formula (V) according to any of to claim 1 , characterized in thatX is halogen,{'sup': '3', 'Ris chlorine,'}{'sup': '4', 'Ris benzyl.'}9. Compounds of the formula (V) according to claim 8 , characterized in thatX is chlorine.10. Compounds of the formula (VII) according to or claim 8 , characterized in that{'sup': '3', 'sub': '3', 'Ris halogen, CN, NO, alkyl, cycloalkyl, haloalkyl, halocycloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino, cycloalkylamino.'} The present invention relates to a process for preparing 1-pyridyl-substituted pyrazoles, ...

Process for preparing 2,2-difluoroethylamine derivatives by alkylation with 2,2-difluoroethyl-1-haloethanes

Process for preparing 2,2-difluorethylamine derivatives of the general formula (III) in which A is an optionally substituted heterocycle as described in the description, by reacting a 2,2-difluoroethyl-1-haloethane compound of the general formula (I) in which Hal is Cl, Br or iodine, with an amine of the general formula (II) in which A is as defined above, optionally in the presence of a base.

Method for Producing Alkenylnitrobenzene Derivatives Unbranched in the 1'-Position

The present invention relates to a process for preparing alkenylnitrobenzenes and alkylanilines, which are of significance as intermediates for fungicidally active alkylanilides.

Tetraarylborate Process for the Preparation of Substituted Biphenyls

The present invention relates to a process for the preparation of substituted biphenyls by reacting aryl halides with tetraarylborates in the presence of palladium catalysts.

Solid form of 4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5H)-one

The present invention relates to a novel solid form of 4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5H)-one, to processes for its preparation and to its use in agrochemical preparations.

Tetraarylborate process for the preparation of substituted biphenyls

The present invention relates to a process for the preparation of substituted biphenyls by reacting aryl halides with tetraarylborates in the presence of palladium catalysts.

Process for Preparing 2,2-difluoroethylamine by Hydrogenating 1,1-difluoro-2-nitroethane

Process for preparing 2,2-difluoroethylamine, characterized in that 1,1-difluoro-2-nitroethane is subjected to a catalytic hydrogenation.

Method for the production of 2-fluoroacyl-3-aminoacrylic acid derivatives

The present invention relates to a process for preparing 2-fluoroacyl-3-aminoacrylic acid derivatives by reacting fluorinated carboxylic acids with dialkylaminoacrylic acid derivatives and acid halides.

Method for the preparation of perfluoroalkyl containing pyrazoles carboxylates

The present invention pertains to a novel process for the preparation of Fluoroalkylpyrazole- or Bisperfluoroalkypyrazole carboxylates comprising a cyclization of Perfluoroalkyl ketoesters with hydrazines.

PROCESS FOR THE PREPARATION OF 5-SUBSTITUTED 1-ALKYLTETRAZOLYL OXIME DERIVATIVES

The present invention relates to a process for the preparation of 5-substituted 1-alkyltetrazolyl oxime derivatives. 3. Process according to claim 1 , characterized in that step (1) is carried out in the presence of a base.4. Process according to claim 3 , characterized in that the molar ratio of base to the oxime of the formula (II) used is 0.8-10.5. Process according to claim 1 , characterized in that step (1) is carried out in a solvent.6. Process according to claim 1 , characterized in that step (2) and (3) are carried out in the presence of a base.7. Process according to claim 6 , characterized in that the molar ratio of base to the compound of the formula (IV) used is 0.8-10.8. Process according to claim 1 , characterized in that the compound of the formula (V) obtained in step (2) is not isolated claim 1 , but is further reacted in situ. The present invention relates to a process for the preparation of 5-substituted 1-alkyltetrazolyl oxime derivatives.5-Substituted 1-alkyltetrazolyl oxime derivatives are important intermediate compounds in active ingredient manufacture or are already fungicidally effective compounds (see e.g. WO 2010/000841). It is already known that 5-substituted 1-alkyltetrazoles can be prepared by lithiation of 1-methyltetrazole at −70° C. (cf. 1971, 49, 2139-2142). However, the yield using the example of 5-benzoyl-1-methyltetrazole is only 41%. The 1-methyltetrazole used likewise has to be prepared in a multistage synthesis sequence. For an industrial reaction, the low temperatures and the expensive use of butyllithium are disadvantageous. Another process for the preparation of 5-benzoyl-1-methyltetrazole is known from 1963, 85, 2967-2976. Benzyl cyanide is reacted with ammonium azide to give 5-benzyltetrazole and then oxidized with chromium trioxide to give 5-benzoyltetrazole. The methylation to 5-benzoyl-1-methyltetrazole takes place with diazomethane. This synthesis route is likewise disadvantageous as regards safety and economical ...

NOVEL METHOD FOR PRODUCING ENAMINOCARBONYL COMPOUNDS

The present invention relates to a process for the preparation of enaminocarbonyl compounds of the formula (I) where compounds of the formula (II) are reacted in the presence of a Brønsted acid to give compounds of the formula (I), and A, R1 and Z are as defined in the description, and also corresponding starting compounds which are used in the process according to the invention.

Process for preparing chiral 3-triazolyl sulphoxide derivatives

The present invention relates to a catalytic process for preparing 3-triazolyl sulphoxide derivatives in enantiomerically pure or enantiomerically enriched form.

Process for preparing substituted pyridines

The invention relates to a process for preparing substituted pyridines in a simple and cost-effective manner in good yields by reacting substituted 1,4-dihydropyridines with methyl nitrite in the presence of an acid that contains less than 20% by weight of oxidizing components.

Process for Preparing Fluorinated Molecules

The present invention relates to a process for preparing α-fluorinated esters from α-hydroxy esters by reaction with a dihalocarbonyl compound (or an equivalent) to give haloformates and further to give fluoroformates, which are then decomposed thermally in the presence of suitable catalysts. The invention further relates to the individual steps of the process and in some cases to novel fluoroformates.

Method for preparing 4-aminobut-2-enolides

Process for preparing 2,2-difluoroethylamine derivatives, wherein compounds of the general formula (IV) are reduced to the corresponding 2,2-difluoroethylamine derivatives of the general formula (III), where the A radical is as defined in the description:

Method for producing 4-aminobut-2-enolides

The present invention relates to a process for preparing 4-aminobut-2-enolides and also corresponding intermediates and starting compounds which are passed through or used in the process according to the invention.

Method for Producing 5-Fluoro-1,3-Dialkyl-1H-Pyrazol-4-Carboxylic Acid Chlorides

The present invention relates to a novel process for preparing known 5-fluoro-1,3-dialkyl-1H-pyrazole-4-carbonyl chlorides which can be used as starting materials for active fungicidal ingredients.

PROCESS FOR PREPARING 2,2-DIFLUOROETHANOL

Process for preparing 2,2-difluoroethanol, comprising the following steps: reacting 1-chloro-2,2-difluoroethane with an alkali metal salt of formic acid or acetic acid in a suitable solvent to give the corresponding 2,2-difluoroethyl formate or 2,2-difluoroethyl acetate, and transesterifying the 2,2-difluoroethyl formate or 2,2-difluoroethyl acetate from step (i) in the presence of an alcohol and optionally of a base. 1. A process for preparing 2 ,2-difluoroethanol , comprising the following steps:(i): reacting 1-chloro-2,2-difluoroethane with an alkali metal salt of formic acid or acetic acid in a suitable solvent to give the corresponding 2,2-difluoroethyl formate or 2,2-difluoroethyl acetate, wherein, 1-chloro-2,2-difluoroethane is added gradually to a mixture, heated to a desired reaction temperature, of solvent and alkali metal salt of formic acid or acetic acid;(ii): transesterifying the 2,2-difluoroethyl formate or 2,2-difluoroethyl acetate from (i) in the presence of an alcohol and optionally of a base.2. The process according to claim 1 , wherein the suitable solvent is at least one selected from the group consisting of dimethyl sulphoxide claim 1 , tetramethylene sulphoxide claim 1 , dipropyl sulphoxide claim 1 , benzyl methyl sulphoxide claim 1 , diisobutyl sulphoxide claim 1 , dibutyl sulphoxide claim 1 , diisoamyl sulphoxide; N claim 1 ,N-dimethylacetamide claim 1 , N-methylformamide claim 1 , N claim 1 ,N-dimethylformamide claim 1 , N claim 1 ,N-dipropylformamide claim 1 , N claim 1 ,N-dibutylformamide claim 1 , N-methylpyrrolidone claim 1 , and N-methylcaprolactam and mixtures thereof.3. The process according to claim 1 , wherein the reaction temperature in (i) in which the 1-chloro-2 claim 1 ,2-difluoroethane is added is in the range from 70° C. to 200° C.4. The process according to claim 1 , wherein gradual addition is understood to mean addition in portions and/or dropwise.5. The process according to claim 1 , wherein 2 claim 1 ,2-difluoroethyl ...

3-Triazolylphenyl-substituted sulphide derivatives as acaricides and insecticides

The present invention constitutes new 3-triazolylphenyl-substituted sulphide derivatives of the formula (I) in which A1, A2, B0, B1, B2, B3, X, R1, R2 and n are as defined in the description, to their use as acaricides and insecticides for controlling animal pests, and to processes for preparing them.

2-phenyl-substituted heterocyclic 1,3-ketoenols as herbicides and pesticides

The present invention relates to new compounds of the formula (I):in whichX, Y and Z have the meanings given in the description andHet represents one of the groups:in whichA, B, D and G have the meanings given in the description,a plurality of processes for their preparation, and to their use as pesticides and herbicides.

PROCESS FOR PREPARING [3-[(6-CHLORO-3-PYRIDINYL)METHYL]-2-THIAZOLIDINYLIDENE]CYANAMIDE

Process for preparing [3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]cyanamide, comprising the following steps: (i) reaction of dimethyl N-cyanocarbonimidodithiocarbonate and 2-aminoethanethiol or a salt thereof in the presence of a base; (ii) reaction of the reaction mixture with 5-chloromethyl-2-chloropyridine, which does not need any purification of the cyanimino-1,3-thiazolidine intermediate.

Method for preparing 4-aminobut-2-enolides

Process for preparing 2,2-difluoroethylamine derivatives, wherein compounds of the general formula (IV) are reduced to the corresponding 2,2-difluoroethylamine derivatives of the general formula (III), where the A radical is as defined in the description:

Process for Preparing 2-Aminooxyethanol

The invention relates to a process for preparing aminoglycol by reacting ketoximes with ethylene oxide under basic conditions to give a substituted 2-hydroxyethyl ketoxime and subsequently reacting the latter with an acid to give aminoglycol.

Process for preparing substituted biphenylanilides

The present invention relates to a process for preparing substituted biphenylanilides of the formula I wherein R1 is a protected amino group which comprises reacting a compound of formula II in the presence of a base and of a palladium catalyst in a solvent, with an organoboron compound of formula (III) ...

3-thiocarbamoylpyrazole derivatives as pesticides

The invention relates to new 3-thiocarbarnoylpyrazole derivatives of the formula (I)in whichAr represents in each case optionally substituted phenyl or pyridyl,R1 represents H2N-CS- andR2 and R3 are as defined in the description,to a plurality of processes for their preparation and to their use as pesticides.

Method for the Production of Substituted and Unsubstituted Cyclohexanone Monoketals

The invention relates to a novel process for preparing and isolating known substituted and unsubstituted 1,4-cyclohexanone monoketals.

Process for the Regioselective Preparation of 1-Alkyl-3-haloalkylpyrazole-4-carboxylic Acid Derivatives

The present invention relates to a process for the regioselective synthesis of 1-alkyl-3-halo-alkylpyrazole-4-carboxylic acid derivatives by cyclization of 2,3-disubstituted acrylic acid derivatives with hydrazines in the presence of carbonyl compounds.

METHOD FOR PRODUCING TETRAZOLE-SUBSTITUTED ANTHRANILIC ACID DIAMIDE DERIVATIVES BY REACTING PYRAZOLIC ACIDS WITH ANTHRANILIC ACID ESTERS

The present invention relates to a process for preparing tetrazole-substituted anthranilic acid diamide derivatives of the formula (1) 3. The process for preparing a compound according to claim 1 , wherein{'sup': 1', '3, 'R, Rindependently of one another represent methyl, ethyl or tert-butyl,'}{'sup': '2', 'Rrepresents fluorine or chlorine,'}{'sup': '4', 'Rrepresents chlorine or cyano,'}Q represents Q-1 or Q-2,{'sup': '5', 'sub': 3', '2', '5, 'Rrepresents CFor CF,'}Z represents N.4. The process for preparing a compound according to claim 1 , wherein Rrepresents CF.5. The process for preparing a compound according to claim 1 , wherein Rrepresents chlorine claim 1 , Rrepresents methyl and Rrepresents cyano.6. The process for preparing a compound according to claim 1 , wherein a ratio of compound of formula (I) in which Q represents Q-1 to compound of formula (I) in which Q represents Q-2 is from 90:10 to 96:4.7. The process for preparing a compound according to claim 1 , wherein reaction of a pyrazole acid of formula (II) with an anthranilic ester of formula (III) is carried out with addition of a base.8. The process for preparing a compound according to claim 1 , wherein a compound of formula (IV) is reacted at a reaction temperature of from 0° C. to +100° C. with a compound of formula (V) to give an anthranilic acid diamide derivative of formula (I). The present invention relates to a process for preparing tetrazole-substituted anthranilic acid diamide derivatives of the formula (I)by reacting N-aryl- and N-hetaryl-substituted pyrazole acids containing methylenetetrazole radicals with anthranilic esters and amines.It has already been described in the literature that tetrazole-substituted anthranilic acid diamide derivatives can be prepared by reacting tetrazole-substituted N-aryl- and N-hetaryl-substituted pyrazole acids with anthranilamides (cf. WO2010/069502). It is also possible to obtain tetrazole-substituted anthranilic acid diamide derivatives by reacting ...

PROCESS FOR PREPARING 2,2-DIFLUOROETHYLAMINE AND SALTS THEREOF PROCEEDING FROM DIFLUOROACETONITRILE

The present invention relates to a process for preparing 2,2-difluoroethylamine of the formula (I) and salts thereof, for example sulphates, hydrochlorides or acetates, which proceeds from difluoroacetonitrile.

Process for the preparation of 5-substituted 1-alkyltetrazolyl oxime derivatives

The present invention relates to a process for the preparation of 5-substituted 1-alkyltetrazolyl oxime derivatives.

Process for preparing tetrazole-substituted anthranilamide derivatives and novel crystal polymorphs of these derivatives

The present invention relates to a process for preparing tetrazole-substituted anthranilamide derivatives of the formula (I) in which R1, R2, R3, R4, R5 and Z are each as defined in the description, and to a novel crystal polymorph of these derivatives and to the use thereof in agrochemical formulations.

Process for the preparation of 5-fluoro-1-alkyl-3-fluoroalky1-1H-pyrazole-4-carbonyl chlorides and fluorides

The present invention relates to a novel process for the preparation of 5-fluoro-1-alkyl-3-fluoroalkyl-1H-pyrazole-4-carbonyl halides and the intermediates occurring in this process, ethyl 5-chloro-1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylate and ethyl 5-fluoro-1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylate.

Solid form of 4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5H)-one

The present invention relates to a novel solid form of 4-[[(6-chloropyridin-3- yl )methyl](2,2-difluoroethyl)amino]furan-2(5H)-one, to processes for its preparation and to its use in agrochemical preparations.

NOVEL METHOD FOR PRODUCING ENAMINOCARBONYL COMPOUNDS

The present invention relates to a process for preparing enaminocarbonyl compounds by reacting compounds of the formula (II) 2. The process according to claim 1 , wherein the Brønsted acid is selected from the group consisting of HPO claim 1 , HSO claim 1 , HCl claim 1 , HBr claim 1 , HF claim 1 , KHSO claim 1 , trifluoroacetic acid claim 1 , acetic acid claim 1 , methanesulphonic acid and p-toluenesulphonic acid.4. The process according to claim 1 , whereA is 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6-chloro-1,4-pyridazin-3-yl, 2-chloro-1,3-thiazol-5-yl, 2-chloropyrimidin-5-yl, 5-fluoro-6-chloropyrid-3-yl, 5,6-dichloropyrid-3-yl, 5-bromo-6-chloropyrid-3-yl, 5-fluoro-6-bromopyrid-3-yl, 5-chloro-6-bromopyrid-3-yl, 5,6-dibromopyrid-3-yl, 5-methyl-6-chloropyrid-3-yl, 5-chloro-6-iodopyrid-3-yl or 5-difluoromethyl-6-chloropyrid-3-yl;{'sup': '1', 'Ris methyl, ethyl, n-propyl, isopropyl, vinyl, allyl, propargyl, cyclopropyl, alkoxyalkyl, 2-fluoroethyl, 2,2-difluoroethyl and 2-fluorocyclopropyl;'}{'sup': 3', '3, 'Z is a chemical moiety —(C═O)ORin which Ris methyl, ethyl, n-propyl, isopropyl or butyl; and'}{'sup': '2', 'sub': 1', '12, 'Ris C-C-alkyl.'}5. The process according to claim 1 , whereA is 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6-chloro-1,4-pyridazin-3-yl, 2-chloro-1,3-thiazol-5-yl, 5-fluoro-6-chloropyrid-3-yl or 5-fluoro-6-bromopyrid-3-yl;{'sup': '1', 'Ris methyl, ethyl, n-propyl, isopropyl, n-prop-2-enyl, n-prop-2-ynyl, cyclopropyl, methoxyethyl, 2-fluoroethyl or 2,2-difluoroethyl;'}{'sub': 2', '2', '3', '2', '3, 'Z is —COCHCHor —COCH; and'}{'sup': '2', 'Ris ethyl, isopropyl or butyl.'}6. The process according to claim 1 , wherein the reacting is performed in a solvent which is at least one selected from the group consisting of dioxane claim 1 , butyronitrile claim 1 , propionitrile claim 1 , acetonitrile claim 1 , DME claim 1 , toluene claim 1 , methyl-THF claim 1 , dichlorobenzene claim 1 , chlorobenzene claim 1 , n-heptane claim 1 , isobutanol ...

Process for the Preparation of 5-Substituted 3-Aryl-3-(trifluoromethyl)-3,4-dihydro-2H-pyrroles

The present invention relates to a process for the manufacturing of 5-substituted 3-aryl-3-(trifluoromethyl)-3,4-dihydro-2H-pyrroles of formula (I) 2. The method according to claim 1 , wherein the metal catalyst used in (i) is selected from the group consisting of copper(I)oxide claim 1 , copper(I)cyanide claim 1 , copper(I)chloride claim 1 , copper(I)bromide claim 1 , copper(I)iodide claim 1 , copper(I)acetate claim 1 , copper(II)cyanide claim 1 , copper(II)chloride claim 1 , copper(II)bromide claim 1 , copper(II)iodide claim 1 , copper(II)oxide claim 1 , copper(II)acetate claim 1 , and copper(II)acetylacetonate.3. The method according to claim 1 , wherein the isomerisation reaction of (ii) is conducted in the presence of an organic or inorganic base claim 1 , and wherein the molar ratio of compound (IV) and the base is in the range from 0.05 to 10.5. The compound according to claim 4 , wherein{'sub': 1', '6, 'X is C-C-alkyl, F, Cl, Br, I, trifluoromethyl, difluoromethoxy, or methoxy;'}n is 1, 2, 3, 4, or 5;Z is carbon or a nitrogen which is optionally substituted with X;{'sup': 10', '10, 'Y is —O-menthyl, —O-α-methylbenzyl, —N(R)(menthyl), or —N(R)(α-methylbenzyl); and'}{'sup': '10', 'sub': 1', '12, 'Ris hydrogen or C-C-alkyl.'}7. The method of claim 1 , wherein the compound of formula (I) is selected from the group consisting of(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl-5-(3-bromo-4-fluorophenyl)-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrole-4-carboxylate; and(1R,2S,5S)-2-isopropyl-5-methylcyclohexyl-5-(3-bromo-4-fluorophenyl)-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrole-4-carboxylate. The present invention relates to a process for the manufacturing of 5-substituted 3-aryl-3-(trifluoromethyl)-3,4-dihydro-2H-pyrroles and two intermediates used in this process.5-Substituted 3-aryl-3-(trifluoromethyl)-3,4-dihydro-2H-pyrroles are useful building blocks (intermediates) for the preparation of insecticidal active compounds ( ...

PROCESS FOR THE PREPARATION OF 2,2-DIFLUOROETHYLAMINE DERIVATIVES STARTING FROM N-(2,2-DIFLUOROETHYL)PROP-2-EN-1-AMINE

Process for the preparation of 2,2-difluoroethylamine derivatives of the formula (IV) 2. The process according to claim 1 , in which step (ii) is carried out in the presence of a catalyst comprising at least one metal from Groups 8-10 of the Periodic Table of the Chemical Elements and optionally in the presence of a nucleophile claim 1 , the nucleophile being at least one selected from hydroxides claim 1 , alkoxides claim 1 , thiolates claim 1 , carbanions claim 1 , halides claim 1 , peroxides claim 1 , cyanides and azides claim 1 , thiols claim 1 , sulphinic acids claim 1 , 2-mercaptobenzoic acid claim 1 , malonic acid and derivatives thereof claim 1 , and B-dicarbonyl compounds claim 1 , barbituric acids claim 1 , N claim 1 ,N′-dimethylbarbituric acid claim 1 , amines and ethanolamine3. The process according to claim 2 , in which the catalyst is a palladium catalyst.4. The process according to claim 3 , in which the catalyst is at least one selected from the group consisting of palladium(0) catalysts claim 3 , 10% palladium-on-charcoal claim 3 , palladium(II) chloride claim 3 , palladium(II) acetate claim 3 , bis(acetylacetonate)palladium(II) claim 3 , dichlorobis(triphenylphosphine)palladium(II) claim 3 , tetrakis(triethylphosphine)palladium and tetrakis(triphenylphosphine)palladium.5. The Process according to claim 1 , in which the inorganic base is at least one selected from the group consisting of hydrides claim 1 , hydroxides claim 1 , amides claim 1 , alkoxides claim 1 , acetates claim 1 , fluorides claim 1 , phosphates claim 1 , carbonates and hydrogencarbonates of alkali metals or alkaline earth metals claim 1 , sodamide claim 1 , sodium hydride claim 1 , lithium diisopropylamide claim 1 , sodium methoxide claim 1 , potassium tert-butoxide claim 1 , sodium hydroxide claim 1 , potassium hydroxide claim 1 , sodium acetate claim 1 , sodium phosphate claim 1 , potassium phosphate claim 1 , potassium fluoride claim 1 , caesium fluoride claim 1 , sodium ...

PROCESS FOR PREPARING PYRIDYL-SUBSTITUTED PYRAZOLES

The present invention relates to a process for preparing 1-pyridyl-substituted pyrazoles, comprising the reaction of acetyleneketones with pyridylhydrazine derivatives to give 1-pyridyl-substituted dihydro-1H-pyrazoles, the further reaction thereof with elimination of water to give 1-pyridyl-substituted trihalomethylpyrazoles, and the further processing thereof. 2. Process for preparing compounds of the formula (I) according to claim 1 , characterized in that{'sup': '1', 'sub': 1', '6, 'Ris (C-C)-alkoxy, halogen,'}{'sup': '2', 'sub': 1', '6', '1', '6, 'Ris (C-C)-alkoxy, aryl(C-C)-alkoxy, fluorine, chlorine, bromine, iodine,'}{'sup': '3', 'sub': 2', '1', '6', '1', '6', '1', '6', '1', '6, 'Ris halogen, CN, NO, (C-C)-alkyl, halo(C-C)-alkyl, (C-C)-alkoxy, halo(C-C)alkoxy.'}3. Process for preparing compounds of the formula (I) claim 1 , characterized in that the preparation of the compound of the formula (V) comprises steps (A) and (B) according to .5. Process for preparing compounds of the formula (I) according to claim 3 ,characterized in that the compounds of the formula (V)in whichX is halogen,{'sup': '4', 'sub': 1', '6', '3, 'Ris a protecting group selected from (C-C)-alkyl, aryl, benzyl, tetrahydropyran, (C═O)-alkyl, (C—O)—Oalkyl, Si(alkyl),'}{'sup': '3', 'sub': '2', 'Ris halogen, CN, NO, alkyl, cycloalkyl, haloalkyl, halocycloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino, cycloalkylamino,'}are converted with addition of alcohol directly to the inventive compounds of the formula (I).6. Compounds of the formula (I) according to claim 1 , characterized in that{'sup': '1', 'Ris halogen,'}{'sup': '2', 'Ris fluorine, chlorine, bromine, iodine,'}{'sup': '3', 'sub': '2', 'Ris halogen, CN, NO, alkyl, cycloalkyl, haloalkyl, halocycloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino, cycloalkylamino.'}7. Compounds of the formula (IV) according to claim 1 , characterized in thatX is halogen,{'sup': '3', 'Ris chlorine,'}{'sup': '4', 'Ris benzyl.'}8. Compounds of the ...

PROCESS FOR THE PREPARATION OF 2,2-DIFLUOROETHYLAMINE STARTING FROM PROP-2-EN-1-AMINE

A process for the preparation of 2,2-difluoroethylamine of the formula (I) 2. The process according to claim 1 , in which stage (ii) is carried out in the presence of a catalyst comprising at least one metal from Groups 8-10 of the Periodic Table and optionally in the presence of a nucleophile claim 1 , the nucleophile being at least one selected from the group consisting of hydroxides claim 1 , alkoxides claim 1 , thiolates claim 1 , carbanions claim 1 , halides claim 1 , peroxides claim 1 , cyanides and azides claim 1 , thiols claim 1 , sulphinic acids claim 1 , 2-mercaptobenzoic acid claim 1 , malonic acid and the derivatives thereof claim 1 , and β-dicarbonyl compounds claim 1 , barbituric acids claim 1 , N claim 1 ,N′-dimethylbarbituric acid claim 1 , amines and ethanolamine.3. The process according to claim 2 , in which the catalyst is a palladium catalyst.4. The process according to claim 3 , in which the catalyst is selected from the group consisting of palladium(0) catalysts claim 3 , 10% palladium-on-charcoal claim 3 , palladium(II) chloride claim 3 , palladium(II) acetate claim 3 , bis(acetylacetonate)palladium(II) claim 3 , dichlorobis(triphenylphosphine)palladium(II) claim 3 , tetrakis(triethylphosphine)palladium and tetrakis(triphenylphosphine)palladium.5. The process according to claim 1 , in which a portion of the prop-2-en-1-amine used acts as said acid scavenger claim 1 , while another portion of the prop-2-en-1-amine used is reacted.6. The process according to claim 1 , in which claim 1 , in stage (i) claim 1 , an organic or inorganic base is used as said acid scavenger.7. The process according to claim 1 , in which stage (i) is carried out without solvent.8. The process according to claim 1 , in which stage (i) is carried out in the presence of a catalyst which is at least one selected from the group consisting of alkali metal bromides and iodides claim 1 , ammonium bromide claim 1 , ammonium iodide claim 1 , tetraalkylammonium bromides claim 1 , ...

PROCESS FOR PREPARING 2,2-DIFLUOROETHYLAMINE FROM 2,2-DIFLUORO-1-CHLOROETHANE AND AMMONIA

Process for preparing 2,2-difluoroethylamine, comprising the following steps: 1. A process for preparing 2 ,2-difluoroethylamine , comprising:(i) mixing 2,2-difluoro-1-chloroethane and gaseous, liquid or supercritical ammonia to form a reaction mixture in a pressure-stable, closed reaction vessel under a pressure of from 10 to 180 bar;(ii) reacting the reaction mixture at a reaction temperature of from 80° C. to 200° C.;(iii) letting down the reaction mixture and isolating 2,2-difluoroethylamine.2. The process according to claim 1 , wherein a catalyst is present in (i) claim 1 , and said catalyst comprises at least one selected from the group consisting of alkali metal bromides claim 1 , alkali metal iodides claim 1 , ammonium bromide claim 1 , ammonium iodide claim 1 , tetraalkylammonium bromides claim 1 , tetraalkylammonium iodides claim 1 , tetraalkylphosphoniumhalides claim 1 , tetraarylphosphonium halides claim 1 , tetrakis(dimethylamino)phosphonium bromide claim 1 , tetrakis(diethylamino)phosphonium bromide claim 1 , tetrakis(dipropylamino)phosphonium bromide and tetrakis(dipropylamino)phosphonium chloride claim 1 , and bis(dimethylamino)[(1 claim 1 ,3-dimethylimidazolidin-2-ylidene)amino]methylium bromide.3. The process according to claim 1 , wherein in (i) claim 1 , the mixing of 2 claim 1 ,2-difluoro-1-chloroethane and ammonia takes place continuously and a static mixer is used for the mixing.4. The process according to claim 1 , carried out completely continuously.5. The process according to claim 4 , wherein said process employs a thermally conditionable flow reactor as a reaction vessel claim 4 , and wherein said reaction vessel comprises at least two zones claim 4 , the first zone comprising a static mixer claim 4 , and wherein (i) takes place in said first zone and (ii) takes place in a second zone which comprises a reaction zone.6. The process according to claim 4 , wherein residence time of 2 claim 4 ,2-difluoro-1-chloroethane and ammonia in a second ...

PROCESS FOR THE PREPARATION OF 2,2-DIFLUOROETHYLAMINE

A process for the preparation of 2,2-difluoroethylamine, comprising the reaction of 2,2-difluoro-1-chloroethane with an imide of the formula (II) 2. The process according to claim 1 , wherein the compound of the formula (II) comprises a salt.3. The process according to claim 1 , wherein the compound of the formula (II) is succinimide and/or phthalimide.4. The process according to claim 1 , wherein the base in (i) is at least one selected from the group consisting of tertiary amines claim 1 , substituted or unsubstituted pyridines and substituted or unsubstituted quinolines claim 1 , triethylamine claim 1 , trimethylamine claim 1 , diisopropylethylamine claim 1 , tri-n-propylamine claim 1 , tri-n-butylamine claim 1 , tri-n-hexylamine claim 1 , tricyclohexylamine claim 1 , N-methylcyclohexylamine claim 1 , N-methylpyrrolidine claim 1 , N-methylpiperidine claim 1 , N-ethylpiperidine claim 1 , N claim 1 ,N-dimethylaniline claim 1 , N-methylmorpholine claim 1 , pyridine claim 1 , 2- claim 1 , 3- or 4-picoline claim 1 , 2-methyl-5-ethylpyridine claim 1 , 2 claim 1 ,6-lutidine claim 1 , 2 claim 1 ,4 claim 1 ,6-collidine claim 1 , 4-dimethylaminopyridine claim 1 , quinoline claim 1 , quinaldine claim 1 , N claim 1 ,N claim 1 ,N claim 1 ,N-tetramethylethylenediamine claim 1 , N claim 1 ,N-dimethyl-1 claim 1 ,4-diazacyclohexane claim 1 , N claim 1 ,N-diethyl-1 claim 1 ,4-diazacyclohexane claim 1 , 1 claim 1 ,8-bis(di-methylamino)naphthalene claim 1 , diazabicyclooctane (DABCO) claim 1 , diazabicyclononene (DBN) claim 1 , diazabicycloundecene (DBU) claim 1 , butylimidazole claim 1 , methylimidazole claim 1 , sodium hydroxide claim 1 , potassium hydroxide claim 1 , lithium hydroxide claim 1 , calcium hydroxide claim 1 , sodium carbonate claim 1 , potassium carbonate claim 1 , sodium hydrogencarbonate claim 1 , potassium hydrogencarbonate and sodium acetate.5. The process according to claim 1 , wherein the base in step (i) is potassium carbonate or sodium carbonate.6. The ...

METHOD FOR PREPARING 4-AMINOBUT-2-ENOLIDES

Process for preparing 2,2-difluoroethylamine derivatives, wherein compounds of the general formula (IV) are reduced to the corresponding 2,2-difluoroethylamine derivatives of the general formula (III), where the A radical is as defined in the description: 2. A compound according to of formula (IIa) in which Ris C-C-alkyl claim 1 , C-aryl claim 1 , or arylalkyl.3. A compound according to of formula (IIa) in which Ris methyl or ethyl.5. A compound according to of formula (IIb) in which Z is sodium or potassium. This application is a Divisional Application of U.S. application Ser. No. 12/677,769 filed Mar. 11, 2010, which is a §371 National Stage Application of PCT/EP2008/007270 filed Sep. 5, 2008, which claims priority to European Application 07116639.1 filed Sep. 18, 2007, each of which is incorporated herein by reference in their entireties.1. Field of the InventionThe present invention relates to a process for preparing 4-amino-but-2-enolides and corresponding intermediates or starting compounds which are passed through or used in the process according to the invention. The present invention further provides processes for preparing the intermediates and starting compounds in question.2. Description of Related ArtParticular substituted 4-aminobut-2-enolide compounds are known as insecticidally active compounds from EP 0 539 588 A1. In addition, International Patent Applications WO 2007/115644, WO 2007/115643 and WO 2007/115646 describe corresponding insecticidally active 4-aminobut-2-enolide compounds.In general, enaminocarbonyl compounds are synthesized from tetronic acid and an amine according to the following scheme 1. This procedure is described, for example, in EP 0 539 588 A1 and in Heterocycles Vol. 27, No. 8, pages 1907 to 1923 (1988).A disadvantage of this process is more particularly that anhydrous tetronic acid is required as a starting compound, the preparation of which is inconvenient and costly.For instance, tetronic acid is generally prepared ...

NOVEL SOLID FORM OF 4-[[(6-CHLOROPYRIDIN-3-YL)METHYL](2,2-DIFLUOROETHYL)AMINO]FURAN-2(5H)-ONE

The present invention relates to a novel solid form of 4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5H)-one, to processes for its preparation and to its use in agrochemical preparations. 1. A solid form of 4-[[(6-chloropyridin-3-yl)methyl](2 ,2-difluoroethyl)amino]furan-2(5H)-one characterized by an X-ray powder diffractogram at 25° C. having the 2Θ (2 theta) values below:2Θ=17.8°2Θ=20.2°2Θ=21.7°2Θ=23.6°2Θ=23.9°2Θ=24.7°2Θ=25.3°.2. A composition comprising the solid form according to and at least one suitable auxiliary.3. A composition for controlling pests comprising a solid form according to and at least one auxiliary suitable for pesticidal uses.4. A composition according to claim 4 , where the pests to be controlled are plant pests claim 4 , animal parasites claim 4 , or insects that damage industrial materials.5. A composition for treating seed comprising a solid form according to and formulation components suitable for seed treatment.6. A method for controlling pests comprising applying the solid form of 4-[[(6-chloropyridin-3-yl)methyl](2 claim 1 ,2-difluoroethyl)amino]furan-2(5H)-one according to to the pests and/or their habitat and/or seed. This application is a Continuation of U.S. application Ser. No. 12/910,201, filed Oct. 22, 2010, which claims priority to European Application No. 09174046.4 filed Oct. 26, 2009 and U.S. Application No. 61/255,600 filed Oct. 28, 2009, the entire contents of which are incorporated herein by reference in their entireties.1. Field of the InventionThe present invention relates to a novel solid form of 4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5H)-one, to a process for preparing this novel solid form and to its advantageous use for preparing stable use forms.2. Description of Related ArtThe compound 4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5H)-one and methods for preparing this compound are known. It is also known that this compound has insecticidal and ...

Process for Preparing Pyridyl-Substituted Pyrazoles

The present invention relates to a process for preparing 1-pyridyl-substituted pyrazoles, comprising the reaction of acetyleneketones with pyridylhydrazine derivatives to give 1-pyridyl-substituted dihydro-1H-pyrazoles, the further reaction thereof with elimination of water to give 1-pyridyl-substituted trihalomethylpyrazoles, and the further processing thereof. 2. Process for preparing compounds of the formula (I) according to claim 1 , characterized in that{'sup': '1', 'sub': 1', '6, 'Ris (C-C)-alkoxy, halogen,'}{'sup': '2', 'sub': 1', '6', '1', '6, 'Ris (C-C)-alkoxy, aryl(C-C)-alkoxy, fluorine, chlorine, bromine, iodine,'}{'sup': '3', 'sub': 2', '1', '6', '1', '6', '1', '6', '1', '6, 'Ris halogen, CN, NO, (C-C)-alkyl, halo(C-C)-alkyl, (C-C)-alkoxy, halo(C-C)alkoxy,'}3. Process for preparing compounds of the formula (I) claim 1 , characterized in that the preparation of the compound of the formula (V) comprises steps (A) and (B) according to .5. Process for preparing compounds of the formula (I) according to claim 3 ,characterized in that the compounds of the formula (V)in whichX is halogen,{'sup': '4', 'sub': 1', '6', '3, 'Ris a protecting group selected from (C-C)-alkyl, aryl, benzyl, tetrahydropyran, (C═O)-alkyl, (C═O)—Oalkyl, Si(alkyl),'}{'sup': '3', 'sub': '2', 'Ris halogen, CN, NO, alkyl, cycloalkyl, haloalkyl, halocycloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino, cycloalkylamino,'}are converted with addition of alcohol directly to the inventive compounds of the formula (I).6. Compounds of the formula (I) according to claim 1 , characterized in that{'sup': '1', 'Ris halogen,'}{'sup': '2', 'Ris fluorine, chlorine, bromine, iodine,'}{'sup': '3', 'sub': '2', 'Ris halogen, CN, NO, alkyl, cycloalkyl, haloalkyl, halocycloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino, cycloalkylamino.'}7. Compounds of the formula (IV) according to claim 1 , characterized in thatX is halogen,{'sup': '3', 'Ris chlorine,'}{'sup': '4', 'Ris benzyl.'}8. Compounds of the ...

Process for Preparing Chiral 3-Triazolyl Sulphoxide Derivatives

The present invention relates to a catalytic process for preparing 3-triazolyl sulphoxide derivatives in enantiomerically pure or enantiomerically enriched form. 2. Process according to claim 1 , characterized in that the enantiomer ratio is 50.5:49.5 to 99.5:0.5 (+):(−) or (−):(+)-enantiomer.3. Process according to either of and claim 1 , characterized in that the enantiomer ratio is 50.5:49.5 to 99.5:0.5 (+):(−) enantiomer.4. Process according to any of to claim 1 , characterized in that{'sup': 1', '2', '1', '2, 'sub': 1', '12, 'Xand X, Yand Yare each independently fluorine, chlorine, hydrogen, (C-C)haloalkyl,'}{'sup': 1', '2, 'sub': 1', '6, 'Rand Rare each independently fluorine, hydrogen, (C-C)alkyl,'}{'sup': '3', 'Ris hydrogen, amino.'}5. Process according to any of to claim 1 , characterized in that{'sup': 1', '2', '1', '2, 'sub': 1', '6, 'Xand X, Yand Yare each independently fluorine, hydrogen, (C-C)haloalkyl,'}{'sup': 1', '2, 'Rand Rare each independently fluorine, methyl,'}{'sup': '3', 'Ris hydrogen.'}6. Process according to any of to claim 1 , characterized in that the oxidizing agents used are organic or inorganic peroxides.8. Process according to any of to claim 1 , characterized in that step (A) is followed by performing a crystallization from organic solvent or a mixture of organic solvent with water.9. Enantiomerically pure or enantiomerically enriched 3-triazolyl sulphoxide derivatives of the formula (I) claim 1 , preparable by the process according to any of to claim 1 , where the enantiomer ratio is 50.5:49.5 to 99.5:0.5 (+):(−)enantiomer. The present invention relates to a catalytic process for preparing 3-thiazolyl sulphoxide derivatives in enantiomerically pure or enantiomerically enriched form.The chemical synthesis of 3-triazolyl sulphoxides is described in the literature, but leads to a racemic mixture (WO 1999/055668).Enantiomerically pure chiral sulphoxides and corresponding derivatives are of great significance in the pharmaceutical and ...

Method for the Regioselective Synthesis of 1-Alkyl-3-Haloalkyl-Pyrazole-4-Carboxylic Acid Derivatives

The present invention relates to a process for the regioselective synthesis of 1-alkyl-3-halo-alkylpyrazole-4-carboxylic acid derivatives by cyclization of 2,3-disubstituted acrylic acid derivatives, and to the hydrazones formed as intermediates in the process. The present invention relates to a process for the regioselective synthesis of 1-alkyl-3-halo-alkylpyrazole-4-carboxylic acid derivatives by cyclization of 2,3-disubstituted acrylic acid derivatives, and to the hydrazones formed as intermediates in the process.2-Dihaloacyl-3-dialkylaminoacrylic esters of the formula II (Y═COOAIk, Z═O) are useful intermediates for the preparation of dihalomethyl-substituted pyrazolylcarboxylic acid derivatives which for their part are precursors of fungicidally active compounds (cf. WO 03/070705).Pyrazolecarboxylic acid derivatives are usually prepared by reacting acrylic acid derivatives having two leaving groups (Z and A) with hydrazines.The reaction with the monoalkylhydrazines gives mainly 1-alkylpyrazoles. However, the cyclization is frequently not regioselective. As a consequence, depending on the substrate and the reaction conditions, the unwanted 5-alkylpyrazoles are formed in amounts between 10 and 80% (see Scheme 1).The synthesis of 1-alkylpyrazolecarboxylic acid derivatives by alkylation of pyrazole derivatives unsubstituted in the 1-position frequently also proceeds with formation of both regioisomers (see Scheme 2).An alternative route of preparing fluorohaloalkylpyrazolecarboxylic acids is the cyclization of, for example, 4,4-dichloro-2-[(dimethylamino)methylidene]-3-oxobutanoate with alkyl-hydrazines followed by a halogen exchange.WO 2005/042468 discloses a process for preparing 2-dihaloacyl-3-aminoacrylic esters by reacting acid halides with dialkylaminoacrylic esters, followed by their cyclization with alkylhydrazines.The European patent application No. 07117232.4, hitherto unpublished, describes a process for preparing HCl-free 2-dihaloacyl-3-aminoacrylic ...

Process for the preparation of substituted n-(benzyl)cyclopropanamines by imine hydrogenation

The present invention relates to a process for the preparation of substituted N-(benzyl)cyclopropanamines of the general formula (II) starting from N-[(aryl)methylene]cyclopropanamine derivatives. The present invention further provides the N-[(arypmethylene]cyclopropanamine derivatives used as starting compounds in this process according to the invention, and their use for the preparation of substituted N (benzyl)cyclopropanamines.

METHOD FOR PREPARING 1-ALKYL-3-DIFLUOROMETHYL-5-FLUOR-1H-PYRAZOLE-4-CARBALDEHYDES AND 1-ALKYL-3-DIFLUOROMETHYL-5-FLUOR-1H-PYRAZOLE-4-CARBOXYLATES

The present invention relates to a novel method for preparing 1-alkyl-3-difluoromethyl-5-fluor-1H-pyrazole-4-carbaldehydes or esters thereof of formula (I) by means of reductive dehalogenation, starting from 1-alkyl-3-chlorodifluoromethyl-5-fluoro-1H-pyrazole-4-carbaldehydes or esters thereof Formula (I) 2. The process according to wherein Ris methyl claim 1 , ethyl claim 1 , n-propyl claim 1 , isopropyl claim 1 , butyl or pentyl.3. The process according to wherein Ris methyl or ethyl.4. The process according to wherein Ris methyl.5. The process according to wherein the catalytic hydrogenation is done in presence of a base.6. The process according to wherein the base is sodium carbonate claim 5 , potassium carbonate claim 5 , sodium bicarbonate claim 5 , potassium bicarbonate claim 5 , mono- claim 5 , di- or trisodium phosphate claim 5 , tripotassium phosphate claim 5 , sodium hydroxide claim 5 , potassium hydroxide claim 5 , triethylamine claim 5 , tributylamine claim 5 , diazabicycloundecene (DBU) claim 5 , diazabicyclononene (DBN) claim 5 , pyridine claim 5 , lutidine claim 5 , 2- claim 5 , 3- or 4-picoline or diazabicyclooctane (DABCO).7. The process according to wherein the base is triethylamine. The present invention relates to a novel method for preparing 1-alkyl-3-difluoromethyl -5-fluor-1H-pyrazole-4-carbaldehydes or esters thereof of formula (I) by means of reductive dehalogenation, starting from 1-alkyl-3-chlorodifluoromethyl-5-fluoro-1H-pyrazole-4-carbaldehydes or esters thereof of formula (II)wherein Ris C-C-alkyl and R is H or C-C-alkoxy.1-Alkyl-3-haloalkyl-5-fluoropyrazolecarbaldehydes and esters thereof are important building blocks for preparing plant protection active ingredients, particularly SDHI fungicides.1-Alkyl-3-difluoromethyl-5-fluor-1H-pyrazole-4-carbaldehydes was so far typically prepared in a multi-stage transformation starting from difluoromethylacetoacetate (WO 2011061205) :Starting material for this transformation, i.e. ...

METHOD FOR PRODUCING SUBSTITUTED ANTHRANILIC ACID DERIVATIVES

The present invention relates to a process for preparing substituted anthranilic acid derivatives of the formula (I) 3. Process according to claim 2 , wherein the compound of formula (IV) is prepared in the presence of a condensing agent and of a base.4. Process according to claim 1 , wherein the palladium catalyst used is a palladium (II) salt and/or Pd(O) species.5. Process according to claim 4 , wherein the palladium catalyst used is bis(dibenzylideneacetone)palladium claim 4 , tris(dibenzylideneacetone)dipalladium claim 4 , palladium chloride claim 4 , palladium bromide and/or palladium acetate.6. Process according to claim 1 , wherein the phosphine ligand used is a compound of formula (X){'br': None, 'sup': 10', '11', '12, 'PRRR\u2003\u2003(X)'}{'sup': 10', '11', '12, 'sub': 1', '8', '1', '8', '6', '10', '1', '8', '1', '10', '1', '8', '6', '10', '6', '10', '1', '8', '1', '8', '1', '8', '1', '8, 'where the R, Rand Rradicals are each independently hydrogen, linear or branched C-C-alkyl, vinyl, aryl or heteroaryl selected from pyridine, pyrimidine, pyrrole, thiophene and furan, which may in turn be substituted by further substituents from the group of linear or branched C-C-alkyl or C-C-aryl, linear or branched C-C-alkyloxy or C-C-aryloxy, halogenated linear or branched C-C-alkyl or halogenated C-C-aryl, C-C-aryloxycarbonyl, linear or branched C-C-alkylamino, linear or branched C-C-dialkylamino, C-C-arylamino, C-C-diarylamino, hydroxyl, carboxyl, cyano and halogen,'}or a chelating biphosphine.7. Process according to claim 6 , wherein the chelating biphosphine is one or more selected from 1 claim 6 ,2-bis(diphenylphosphino)ethane claim 6 , 1 claim 6 ,2-bis(diphenylphosphino)propane claim 6 , 1 claim 6 ,2-bis(diphenylphosphino)butane claim 6 , 2 claim 6 ,2′-bis(diphenylphosphino)-1 claim 6 ,1′-binaphthyl and 1 claim 6 ,1′-bis(diphenylphosphino)ferrocene.8. Process according to claim 6 , wherein the phosphine ligand used is triphenylphosphine.9. Process according to ...

METHOD FOR PRODUCING 3,5-BIS(FLUOROALKYL)-PYRAZOL-4-CARBOXYLIC ACID DERIVATIVES AND 3,5-BIS(FLUOROALKYL)-PYRAZOLES

The present invention relates to novel 3,5-bis(fluoroalkyl)pyrazole-4-carboxylic acid derivatives and to a process for preparing 3,5-bis(fluoroalkyl)pyrazole-4-carboxylic acid derivatives and 3,5-bis(fluoroalkyl)pyrazoles. 2. Process according to claim 1 , wherein{'sup': '1', 'sub': 1-12', '2', '2', '1-12, 'Ris selected from the group consisting of H, C-alkyl, CHCN, CHCOO—(C)-alkyl, and'}{'sup': 2', '3, 'sub': 3', '2', '2, 'Rand Rare each independently selected from the group consisting of CF, CFH, CFCl;'}{'sup': 4', '5', '5', '6', '5', '6', '5', '6, 'sub': 1-12', '3-8', '6-18', '7-19', '7-19, 'Ris selected from the group consisting of COOH, (C═O)OR, CN and (C═O)NRR, where Rand Rare each independently selected from the group comprising C-alkyl, C-cycloalkyl, C-aryl, C-arylalkyl and C-alkylaryl, or where Rand Rtogether with the nitrogen atom to which they are bonded may form a five- or six-membered ring.'}3. Process according to claim 1 , wherein{'sup': '1', 'sub': 3', '2', '1-12, 'Ris selected from the group comprising H, CH, CHCOO—(C)-alkyl, and'}{'sup': 2', '3, 'sub': 3', '2', '2, 'Rand Rare each independently selected from the group consisting of CF, CFH, CFCl;'}{'sup': 4', '5, 'Ris selected from the group consisting of COOH, (C═O)OR.'}5. Compound of formula (Ia) and (Ib) according to claim 4 , wherein{'sup': 1', '5, 'sub': 2', '2', '2', '2', '3, 'claim-text': 'X is independently F, Cl;', 'Ris selected from H, methyl, CHCOOH, CHCOOR, CHCN, CHCX{'sup': 2', '3, 'Rand Rare selected from difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and 1,1,1-trifluoroprop-2-yl;'}{'sup': '4', 'sub': 3', '3', '7', '2', '2, 'Ris selected from the group consisting of H, BR, COOCH, COOEt, COOCH, CN and CONMe, CONEt.'}6. Compound of formula (Ia) and (Ib) ...

PROCESS FOR PREPARING SUBSTITUTED PHENYLISOXAZOLINE DERIVATIVES

The present invention relates to a process for preparing substituted phenylisoxazoline derivatives. 2. Compound of formula (IV) according to claim 1 ,wherein{'sup': '2', 'Ris chlorine;'}{'sup': '3', 'Ris methylsulphonyloxy and'}{'sup': '4', 'Ris methyl, ethyl.'}4. Compound of formula (Ia) according to claim 3 ,wherein{'sup': '2', 'Ris chlorine and'}{'sup': '3', 'Ris methylsulphonyloxy.'}6. Compound of formula (Ib) according to claim 5 ,wherein{'sup': '2', 'Ris chlorine;'}{'sup': '3', 'Ris methylsulphonyloxy and'}X is bromine.7. A product comprising the compound of formula (Ia) according to for production of one or more active fungicidal ingredients.8. A product comprising the compound of formula (Ib) according to for production of one or more active fungicidal ingredients. This application is Divisional Application of U.S. patent application Ser. No. 15/548,216, filed Aug. 2, 2017, which is a § 371 National Stage Application of PCT/EP2016/054192, filed Feb. 29, 2016, which claims priority to European Application No. 15157803.6 filed Mar. 5, 2015. Each of these applications is incorporated by reference in its entirety.The present invention relates to a process for preparing substituted phenylisoxazoline derivatives.Substituted phenylisoxazoline derivatives are useful intermediates in the production of active agrochemical ingredients (see, for example, WO 2008/013925, WO 2009/094407, WO 2010/123791).There are various known processes for preparing such substituted phenylisoxazoline derivatives.WO 2011/085170 describes, for example, a process for preparing these phenylisoxazoline derivatives by [3+2] cycloaddition with a chloroxime with a styrene and downstream Grignard addition and halogenation (Scheme 1).A disadvantage of this process is that the use of further functional groups which can react directly with a Grignard reagent is impossible.WO 2011/085170 describes, for example, a process for preparing these phenylisoxazoline derivatives by [3+2] cycloaddition with a ...

PROCESS FOR PREPARING TETRAZOLE-SUBSTITUTED ANTHRANILAMIDE DERIVATIVES AND NOVEL CRYSTAL POLYMORPHS OF THESE DERIVATIVES

The present invention relates to a process for preparing tetrazole-substituted anthranilamide derivatives of the formula (I) 3. Crystal polymorph B according to claim 1 , wherein the x-ray powder diffractogram thereof using Cu Kα radiation corresponds essentially to the spectrum reproduced in .5. Crystal polymorph B according to claim 1 , having a Raman spectrum that corresponds essentially to the spectrum reproduced in .6. Agrochemical composition comprising the compound of the formula (I-1) of crystal polymorph B according to .7. Method for controlling unwanted insects claim 1 , comprising applying an agrochemical composition comprising the compound of the formula (I-1) of crystal polymorph B according to to insects and/or their habitat and/or seed. This application is a divisional application of U.S. application Ser. No. 13/159,961 filed Jun. 14, 2011, which claims priority to EP 10166059.5 filed Jun. 15, 2010 and U.S. 61/354,920 filed Jun. 15, 2010, the contents of which are incorporated by reference in their entireties.The present invention relates to a process for preparing tetrazole-substituted anthranilamide derivatives of the formula (I)by conversion of N-aryl- and N-hetaryl-substituted pyrazoles which contain methylenetetrazole radicals. The present invention further relates to the provision of a novel crystal polymorph of the corresponding anthranilamide derivatives by this process, and to the novel crystal polymorph and to the use thereof in agrochemical formulations.The literature has already stated that, for example, the alkylation of alkyltetrazoles with, for example, alkyl iodides typically leads to a mixture of different regioisomers. In addition, the composition of the mixture depends strongly on the particular substituents on the tetrazole ring. For instance, William P. Norris, in J. Org. Chem., 1962, 27 (9), 3248-3251, states that the alkylation of 5-trifluoromethyltetrazole with methyl iodide gives rise to a mixture of the two regioisomers in a ...

Process for preparing substituted phenylisoxazoline derivatives

The present invention relates to a process for preparing substituted phenylisoxazoline derivatives. 2. Process according to claim 1 , wherein{'sup': '1', 'Ris methyl, bromomethyl, chloromethyl;'}{'sup': '2', 'Ris chlorine or bromine;'}{'sup': '3', 'Ris methylsulphonyloxy or ethylsulphonyloxy;'}{'sup': '4', 'sub': 1', '4, 'Ris C-C-alkyl and'}X is chlorine or bromine.3. Process according to claim 1 , wherein{'sup': '1', 'Ris methyl, bromomethyl;'}{'sup': '2', 'Ris chlorine;'}{'sup': '3', 'Ris methylsulphonyloxy;'}{'sup': '4', 'Ris methyl, ethyl and'}X is bromine.4. Process according to claim 1 , wherein claim 1 , in (ii) claim 1 , triethylamine is used as base and methylmagnesium bromide or methylmagnesium chloride as organometallic reagent.6. Compound of formula (IV) according to claim 5 ,wherein{'sup': '2', 'Ris chlorine;'}{'sup': '3', 'Ris methylsulphonyloxy and'}{'sup': '4', 'Ris methyl, ethyl.'}8. Compound of the formula (Ia) according to claim 7 ,wherein{'sup': '2', 'Ris chlorine and'}{'sup': '3', 'Rmethyl sulphonyloxy.'}10. Compound of formula (Ib) according to claim 9 ,wherein{'sup': '2', 'Ris chlorine;'}{'sup': '3', 'Ris methylsulphonyloxy and'}X is bromine.11. A product comprising the compound of formula (Ia) according to for production of one or more active fungicidal ingredients.12. A product comprising the compound of formula (Ib) according to for production of one or more active fungicidal ingredients. The present invention relates to a process for preparing substituted phenylisoxazoline derivatives.Substituted phenylisoxazoline derivatives are useful intermediates in the production of active agrochemical ingredients (see, for example, WO 2008/013925, WO 2009/094407, WO 2010/123791).There are various known processes for preparing such substituted phenylisoxazoline derivatives.WO 2011/085170 describes, for example, a process for preparing these phenylisoxazoline derivatives by [3+2] cycloaddition with a chloroxime with a styrene and downstream Grignard ...

METHOD FOR PRODUCING SUBSTITUTED ANTHRANILIC ACID DERIVATIVES

The present invention relates to a process for preparing substituted anthranilic acid derivatives of the formula (I) 3. Process according to claim 2 , wherein the compound of formula (IV) is prepared in the presence of a condensing agent and of a base.4. Process according to claim 1 , wherein the palladium catalyst used is a palladium(II) salt and/or Pd(0) species.5. Process according to claim 4 , wherein the palladium catalyst used is bis(dibenzylideneacetone)palladium claim 4 , tris(dibenzylideneacetone)dipalladium claim 4 , palladium chloride claim 4 , palladium bromide and/or palladium acetate.6. Process according to claim 1 , wherein the phosphine ligand used is a compound of formula (X){'br': None, 'sup': 10', '11', '12, 'PRRR\u2003\u2003(X)'}{'sup': 10', '11', '12, 'sub': 1', '8', '1', '8', '6', '10', '1', '8', '1', '10', '1', '8', '6', '10', '6', '10', '1', '8', '1', '8', '1', '8', '1', '8, 'where the R, Rand Rradicals are each independently hydrogen, linear or branched C-C-alkyl, vinyl, aryl or heteroaryl selected from pyridine, pyrimidine, pyrrole, thiophene and furan, which may in turn be substituted by further substituents from the group of linear or branched C-C-alkyl or C-C-aryl, linear or branched C-C-alkyloxy or C-C-aryloxy, halogenated linear or branched C-C-alkyl or halogenated C-C-aryl, C-C-aryloxycarbonyl, linear or branched C-C-alkylamino, linear or branched C-C-dialkylamino, C-C-arylamino, C-C-diarylamino, hydroxyl, carboxyl, cyano and halogen, or a chelating biphosphine.'}7. Process according to claim 6 , wherein the chelating biphosphine is one or more selected from 1 claim 6 ,2-bis(diphenylphosphino)ethane claim 6 , 1 claim 6 ,2-bis(diphenylphosphino)propane claim 6 , 1 claim 6 ,2-bis(diphenylphosphino)butane claim 6 , 2 claim 6 ,2′-bis(diphenylphosphino)-1 claim 6 ,1′-binaphthyl and 1 claim 6 ,1′-bis(diphenylphosphino)ferrocene.8. Process according to claim 6 , wherein the phosphine ligand used is triphenylphosphine.9. Process according to ...

METHOD FOR PRODUCING PYRAZOLYLCARBOXANILIDES

The present invention relates to a simplified process for preparing pyrazolylcarboxanilides by reacting pyrazolylcarboxylic esters with anilines in the presence of a base and removing at least one reaction product. 2. The process according to claim 1 , wherein the pyrazolylcarboxylic ester used as a starting material is of formula (I) where{'sup': '5', 'Rrepresents methyl, ethyl or benzyl.'}3. The process according to claim 1 , wherein the starting material used comprises an aniline of formula (II) where{'sup': '3', 'Rrepresents hydrogen, fluorine or chlorine,'}n represents 1 or 2,{'sup': '4', 'sub': 2', '4, 'Rrepresents phenyl optionally substituted two or three times by the same substituent selected from fluorine and chlorine, or represents C-C-haloalkoxy each having from 3 to 6 fluorine atoms and from 0 to 1 chlorine atom;'}{'sub': 3', '1', '4, 'or represents C-bicycloalkyl each optionally substituted from one to four times by an identical or different substituent selected from halogen and C-C-alkyl;'}{'sub': 2', '6, 'or represents an unsubstituted (linear or branched) C-C-alkyl;'}or combines with a phenyl radical to represent both syn isomers of N-[(1RS,4SR,9RS)-1,2,3,4-tetrahydro-9-(isopropyl)-1,4-methanonaphthalene, or both anti isomers of N-[(1RS,4SR,9SR)-1,2,3,4-tetrahydro-9-sopropyl-1,4-methanonaphthalene;or combines with a phenyl radical to represent N-[(1RS,4SR)-1,2,3,4-tetrahydro-9-(dichloromethylene)-1,4-methanonaphthalene;or combines with a phenyl radical to represent N-(1,3-dihydro-1,1,3-trimethyl-4-isobenzofuranyl.4. The process according to claim 1 , wherein the aniline used as a starting material is of formula (II) where{'sup': '3', 'Rrepresents 5-fluorine,'}n represents 1, and{'sup': '4', 'Rrepresents 3,4,5-trifluorophenyl; or'}represents 2-(1,1,2,2-tetrafluoroethoxy), 2-(1,1,2,3,3,3-hexafluoropropoxy) or 2-(3-Cl-1,1,2-trifluoroethoxy); orrepresents 2-(1,1′-bicyclopropyl); orrepresents 2-(1,3-dimethylbutyl); orcombines with a phenyl radical to ...

Fungicide pyrazole carboxamides derivatives

The present invention relates to pyrazole carboxamides derivatives of formula (1) wherein Y represents CR 5 or N, T represents S or O, X1 and X2 represent a chlorine or a fluorine atom, and Z1 represents a substituted or non-substituted cyclopropyl; Their process of preparation, their use as fungicide, and/or anti-mycotoxin active agents, and/or insecticide, and/or nematicide, particularly in the form of fungicide compositions, and methods for the control of phytopathogenic fungi, notably of plants, using these compounds or compositions.

Process for preparing 3,5-bis(haloalkyl)pyrazole derivatives from a,a-dihaloamines and ketimines

The present invention relates to a novel process for preparing 3,5-bis(haloalkyl)pyrazole derivatives from α,α-dihaloamines and ketimines. 2. Process according to claim 1 , wherein{'sup': 1', '3, 'sub': '3', 'Rand Rare each independently selected from difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, tetrafluoroethyl (CFCFH), pentafluoroethyl and 1,1,1-trifluoroprop-2-yl;'}{'sup': '2', 'sub': 3', '2', '5', '3', '7', '3', '2', '2', '5', '2, 'Ris selected from H, F, Cl, Br, COOCH, COOCH, COOCH, CN and CON(CH), CON(CH);'}{'sup': '4', 'sub': 1', '8', '2', '1', '8, 'Ris selected from H, C-C-alkyl, CHCOOC-C-alkyl, phenyl, pyridyl;'}{'sup': '8', 'sub': 7', '19, 'Rare each independently selected from methyl, ethyl, n-, iso-propyl, n-, iso-, sec- and t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, benzyl, phenylethyl, C-C-alkylaryl, tolyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-dimethylphenyl;'}X is independently selected from F or Cl;{'sup': 10', '11, 'sub': 1', '12', '3', '8', '7', '19, 'Rand Rare each independently selected from C-C-alkyl, C-C-cycloalkyl, C-C-arylalkyl or'}{'sup': 10', '11, 'Rand Rtogether with the nitrogen atom to which they are bonded may form a five-membered ring.'}3. Process according to claim 1 , wherein{'sup': 1', '3, 'Rand Rare each independently selected from trifluoromethyl, difluoromethyl, difluorochloromethyl, pentafluoroethyl;'}{'sup': '2', 'sub': 2', '5, 'Ris selected from H, Cl, CN, COOCH;'}{'sup': '4', 'sub': 2', '3', '2', '2', '3, 'Ris selected from H, methyl, ethyl, n-, isopropyl, n-, iso-, sec- and t-butyl, n-pentyl, n-hexyl, 1,3-dimethylbutyl, 3,3-dimethylbutyl, phenyl, CHCOOCH, CHCOOCHCH;'}{'sup': '8', 'sub': 7', '19, 'Ris selected from methyl, ethyl, n-, iso-propyl, n-, iso-, sec- and t-butyl, cyclopropyl, ...

PROCESS FOR PREPARING 3,5-BIS(FLUOROALKYL)PYRAZOLE DERIVATIVES FROM a,a-DIHALOAMINES

The present invention relates to a novel process for preparing 3,5-bis(fluoroalkyl)pyrazole derivatives from α,α-dihaloamines. 2. Process according to claim 1 , wherein{'sup': 1', '3, 'sub': '3', 'Rand Rare each independently selected from difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, tetrafluoroethyl (CFCFH), pentafluoroethyl, 1,1,1-trifluoroprop-2-yl, trifluoromethylphenyl, bis(trifluoromethyl)phenyl, fluorophenyl and difluorophenyl;'}{'sup': '2', 'sub': 3', '2', '5', '3', '7', '3', '2', '2', '5', '2, 'Ris selected from H, Br, COOCH, COOCH, COOCH, CN, CON(CH)and CON(CH);'}{'sup': 6', '7', '8', '9, 'sub': '7-19', 'R, RRand Rare each independently selected from H, methyl, ethyl, n- and iso-propyl, n-, iso-, sec- and t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, benzyl, phenylethyl, C-alkylaryl, tolyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-dimethylphenyl;'}{'sup': 6', '7, 'Rand Rcan also form a 5- or 6-membered ring and'}X is independently selected from F or Cl.3. Process according to claim 1 , wherein{'sup': 1', '3, 'Rand Rare each independently selected from trifluoromethyl, difluoromethyl, difluorochloromethyl, pentafluoroethyl;'}{'sup': '2', 'sub': 2', '5, 'Ris selected from H, Cl, CN, COOCH;'}{'sup': 6', '7', '8', '9, 'R, RRand Rare each independently selected from, methyl, ethyl, n- and iso-propyl, n-, iso-, sec- and t-butyl, cyclopropyl, phenyl, benzyl, tolyl and'}X is independently selected from F or Cl.4. Process according to claim 1 , wherein{'sup': 1', '3, 'sub': '2', 'Rand Rare CFH;'}{'sup': '2', 'sub': 2', '5, 'Ris selected from H or COOCH;'}{'sup': 6', '7', '8', '9, 'R, RRand Rare each independently selected from methyl and phenyl;'}X is F.5. Process according to claim 1 , wherein{'sup': 1', '3, 'sub': '2', 'Rand Rare CFH ...

PROCESS FOR PREPARING 3,5-BIS(HALOALKYL)PYRAZOLE DERIVATIVES VIA ACYLATION OF HYDRAZONES

Process for preparing 3,5-bis(haloalkyl)pyrazole derivatives of the formula (I), via acylation of Hydrazones. 2. A process according to claim 1 , characterized in that{'sup': 1', '3, 'sub': '3', 'Rand Rare each independently selected from the group consisting of difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, tetrafluoroethyl (CFCFH), pentafluoroethyl and 1,1,1-trifluoroprop-2-yl;'}{'sup': '2', 'sub': 3', '2', '5', '3', '7', '3', '2', '2', '5', '2, 'Ris selected from the group consisting of H, F, Cl, Br, COOCH, COOCH, COOCH, CN, CON(CH), and CON(CH);'}{'sup': '9', 'Ris selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, benzyl, phenylethyl, tolyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, and 3,5-dimethylphenyl;'}{'sup': '1', 'X is selected from the group consisting of F, Cl and —OC(O)R; and'}{'sup': '10', 'sub': 1-12', '3-8', '7-19, 'Ris selected from the group consisting of C-alkyl, C-cycloalkyl, and C-arylalkyl.'}3. A process according to claim 1 , characterized in that{'sup': 1', '3, 'Rand Rare each independently selected from the group consisting of trifluoromethyl, difluoromethyl, difluorochloromethyl, and pentafluoroethyl;'}{'sup': '2', 'sub': 2', '5', '2, 'Ris selected from the group consisting of H, Cl, CN, and COO(CH);'}{'sup': '9', 'Ris selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and benzyl;'}{'sup': '1', 'X is selected from the group consisting of F, Cl and —OC(O)R; and'}{'sub': R', '1-12', '3-8, 'sup': '10', 'is selected from the group consisting of C- ...

PROCESS FOR PREPARING 3,5-BIS(HALOALKYL)PYRAZOLES VIA ACYLATION OF KETIMINES

The present invention relates to a novel process for preparing 3,5-bis(haloalkyl)pyrazole derivatives of the formula Ia) and (Ib), via acylation of ketimines. 2. The process according to claim 1 , characterized in that Rand Rare each independently selected from the group consisting of difluoromethyl claim 1 , trifluoromethyl claim 1 , chlorofluoromethyl claim 1 , dichlorofluoromethyl claim 1 , chlorodifluoromethyl claim 1 , 1-fluoroethyl claim 1 , 2-fluoroethyl claim 1 , 2 claim 1 ,2-difluoroethyl claim 1 , 2 claim 1 ,2 claim 1 ,2-trifluoroethyl claim 1 , 2-chloro-2-fluoroethyl claim 1 , 2-difluoroethyl claim 1 , 2 claim 1 ,2-dichloro-2-fluoroethyl claim 1 , 2 claim 1 ,2 claim 1 ,2-trichloroethyl claim 1 , tetrafluoroethyl (CFCFH) claim 1 , pentafluoroethyl claim 1 , and 1 claim 1 ,1 claim 1 ,1-trifluoroprop-2-yl;{'sup': '2', 'sub': 3', '2', '5', '3', '7', '3', '2', '2', '5', '2, 'Ris selected from the group consisting of H, F, Cl, Br, COOCH, COOCH, COOCH, CN, CON(CH), and CON(CH);'}{'sup': '4', 'sub': 1', '8, 'Ris selected from the group consisting of H, C-Calkyl, aryl, and pyridyl;'}{'sup': '8', 'Ris selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, benzyl, phenylethyl, tolyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, and 3,5-dimethylphenyl; and'}{'sup': '1', 'X is selected from F, Cl, or —O(CO)R.'}3. The process according to claim 1 , characterized in that{'sup': 1', '3, 'Rand Rare each independently selected from the group consisting of trifluoromethyl, difluoromethyl, difluorochloromethyl, and pentafluoroethyl;'}{'sup': '2', 'sub': 2', '5', '2, 'Ris selected from the group consisting of H, Cl, CN, and COO(CH);'}{'sup': '4', 'Ris selected from the group consisting of H, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, t-butyl, n-pentyl, n-hexyl, 1,3-dimethylbutyl, 3 ...

METHOD FOR THE PRODUCTION OF 3,5-BIS(FLUOROALKYL)PYRAZOLE DERIVATIVES

The present invention describes a novel method for preparing 3,5-bis(fluoroalkyl)pyrazole derivatives. 2. Method according to claim 2 , wherein{'sup': 1', '3, 'Rand Rare each independently selected from difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and 1,1,1-trifluoroprop-2-yl;'}{'sup': '2', 'sub': 3', '2', '5', '3', '7', '3', '2', '3', '7, 'Ris selected from H, Cl, COOH, COOCH, COOCH, COOCH, CN and CON(CH), CONCH;'}{'sup': '4', 'Z is selected from O, S, N—R;'}{'sup': '4', 'sub': '7-19', 'Ris selected from methyl, ethyl, n-propyl, isopropyl, n-, sec- and t-butyl, isobutyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, benzyl, phenylethyl, C-alkylaryl, tolyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-dimethylphenyl;'}{'sup': '6', 'sub': '7-19', 'Ris selected from methyl, ethyl, n-propyl, isopropyl, n-, sec- and t-butyl, isobutyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, benzyl, phenylethyl, C-alkylaryl, tolyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-dimethylphenyl or'}{'sup': 4', '6, 'Rand Rform a piperidine or morpholine ring together with the nitrogen atom to which they are attached;'}{'sup': 7', '8, 'sub': '7-19', 'Rand Rare each independently selected from H, methyl, ethyl, n-propyl, isopropyl, n-, sec- and t-butyl, isobutyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, benzyl, phenylethyl, C-alkylaryl, tolyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-dimethylphenyl or'}{'sup': 7', '8, 'Rand Rform a five- or six-membered ring.'}3. Method according to claim 1 , wherein{'sup': 1', '3, 'Rand Rare each independently selected from trifluoromethyl, difluoromethyl, difluorochloromethyl, pentafluoroethyl;'}{'sup': '2', 'sub': '3', 'Ris selected from H, F, Cl, Br, COOH, COOCH, CN;'}{'sup': '4', 'Z ...

PROCESS FOR PREPARING 1-ALKYL-3-FLUOROALKYL-1H-PYRAZOLE-4-CARBOXYLIC ACID CHLORIDES

The present invention relates to a novel method for preparing 1-alkyl-3-fluoroalkyl-1H-pyrazole-4-carbonyl chlorides, a useful precursor for the preparation of fungicides, by means of reductive dehalogenation, starting from N-alkyl-3-haloalkyl-5-halopyrazolecarbaldehyde. 2. Method according to claim 1 , wherein 5-halo-1-alkyl-3-fluoroalkyl-1H-pyrazole-4-carbaldehyde of formula (II) where Ris methyl claim 1 , ethyl claim 1 , n-propyl claim 1 , isopropyl claim 1 , butyl claim 1 , pentyl claim 1 , Ris CFH claim 1 , CF claim 1 , CFCl claim 1 , CClF claim 1 , CF claim 1 , CFand Hal is Cl is used.3. Method according to claim 1 , wherein 5-halo-1-alkyl-3-fluoroalkyl-1H-pyrazole-4-carbaldehyde of formula (II) where Ris methyl claim 1 , Ris CFH or CFand Hal is Cl is used.4. Method according to claim 1 , wherein 5-chloro-1-methyl-3-difluoromethyl-1H-pyrazole-4-carbaldehyde (II-1) is used.5. Method according to claim 1 , wherein the catalytic hydrogenation is carried out using a palladium catalyst supported on calcium carbonate.6. Method according to claim 1 , wherein catalytic hydrogenation is carried out at a temperature of 0° C. to 100° C.7. Method according to claim 1 , wherein catalytic hydrogenation is carried out at a pressure of 1 to 20 bar.8. Method according to claim 1 , wherein the base added to the catalytic hydrogenation is triethylamine.9. Method according to claim 1 , wherein 0.5 to 5 molar equivalents of base claim 1 , based on the compound of formula (II) claim 1 , is added in the catalytic hydrogenation.10. Method according to claim 1 , wherein SOClis used as chlorinating agent.11. Method according to claim 1 , wherein the free-radical initiator is selected from the group consisting of 2 claim 1 ,2′-azobis(isobutyronitrile) claim 1 , 2 claim 1 ,2′-azobis(2 claim 1 ,4-dimethylvaleronitrile) claim 1 , di(2-ethylhexyl) peroxydicarbonate claim 1 , tert-amyl peroxy-2-ethylhexanoate and tert-butyl peroxy-2-ethylhexanoate.12. Method according to claim 1 , wherein ...

PROCESS FOR THE PREPARATION OF 5-FLUORO-1H-PYRAZOLES

A new process for the preparation of 5-fluoro-1H-pyrazoles of the general formula (I) 2. Process according to claim 1 , wherein{'sup': '1', 'Ris methyl'}{'sup': '2', 'sub': '3', 'Ris CF'}{'sup': '3', 'sub': 2', '5, 'Ris CF,'}3. Process according to claim 1 , wherein the base is triethylamine 5-fluoro-1H-pyrazoles, in particular 5-Fluoro-1-methyl-3-pentafluoroethyl-4-trifluoromethyl-1H-pyrazole, are important building blocks for the preparation of crop protection chemicals, as those described in WO 2010051926.It is known that 5-fluoro-1 -methyl-3-pentafluoroethyl-4-trifluoromethyl-1H-pyrazole can be prepared by the treatment of the dimer of hexafluoropropene with water free N,N-dimethylhydrazine in diethyl ether at −50° C. followed by heating of the intermediate at 120° C., I. L. Knunyants et al. Izv. Akad. Nauk SSSR, (1990) 2583-2589.However, this two step transformation requires low temperatures for the first step and results in the formation of CHF during the thermal elimination in the second step, making this process expensive, environmentally unfriendly, and particularly difficult for industrializationStarting from perfluoro-2-methyl-2-penten and phenylhydrazine, in the presence of triethylamine at −50° C. 1-Phenylpyrazole was prepared in 90% yield (SU 1456419). Furin et al. J. Fluor. Chem. 98(1999) 29 reported that the areaction of perfluoro-2-methyl-2-penten with phenylhydrazine in CHCN gave a mixture of isomeric pyrazoles 3 and 4 in a ratio 4:1.The utilization of the commercially available and cheap monoalkylhydrazines (especially in the form of their water solutions) for the regioselective synthesis of the said pyrazoles is not known to the person of ordinary skill in the art.The problem to be solved by this invention was to identify a simple and selective process for preparing 5-fluoro-1H-pyrazoles from available fluoroalkenes and mono-substituted hydrazines, which should in particular be amenable for an industrial scale process.Surprisingly, 5-fluoro-1H- ...

Process for Preparing Chiral 3-Triazolyl Sulphoxide Derivatives

The present invention relates to a catalytic process for preparing 3-triazolyl sulphoxide derivatives in enantiomerically pure or enantiomerically enriched form.

METHOD FOR PRODUCING 3,5-BIS(FLUOROALKYL)-PYRAZOL-4-CARBOXYLIC ACID DERIVATIVES AND 3,5-BIS(FLUOROALKYL)-PYRAZOLES

The present invention relates to novel 3,5-bis(fluoroalkyl)pyrazole-4-carboxylic acid derivatives and to a process for preparing 3,5-bis(fluoroalkyl)pyrazole-4-carboxylic acid derivatives and 3,5-bis(fluoroalkyl)pyrazoles. 2. Compound of formula (Ia) or (Ib) according to claim 1 , wherein{'sup': 1', '5, 'sub': 2', '2', '2', '2', '3, 'claim-text': 'X is independently F or Cl;', 'Ris selected from H, methyl, CHCOOH, CHCOOR, CHCN, or CHCX{'sup': 2', '3, 'Rand Rare selected from difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro, 2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1,1,1-trifluoroprop-2-yl;'}{'sup': '4', 'sub': 3', '3', '7', '2', '2, 'Ris selected from the group consisting of H, BR, COOCH, COOEt, COOCH, CN, CONMe, and CONEt.'}3. Compound of formula (Ia) or (Ib) according to claim 1 , wherein{'sup': '1', 'sub': 2', '2', '2, 'Ris selected from H, CHCOOH, CHCOOMe, or CHCN,'}{'sup': 2', '3, 'Rand Rare selected from the group consisting of trifluoromethyl, difluoromethyl, difluorochloromethyl, and pentafluoroethyl;'}{'sup': '4', 'Ris selected from the group consisting of H, Br, and COOH.'}4. Compound of formula (Ia) or (Ib) according to claim 1 , wherein{'sup': 2', '3', '4, 'sub': '2', 'R1=H; R═R═CFH and R=COOEt.'}5. Compound of formula (Ia) or (Ib) according to claim 1 , wherein{'sup': 1', '2', '3', '4, 'sub': '2', 'R═H; R═R═CFH and R═COOH.'}6. Compound of formula (Ia) or (Ib) according to claim 1 , wherein{'sup': 1', '2', '3', '4, 'sub': 2', '2, 'R=CHCOOEt; R═R═CFH and R=COOEt.'} This application is a Divisional application of Ser. No. 14/375,450 filed Jul. 30, 2014, which is a §371 National Stage application of PCT/EP2013/051930, filed Jan. 31, 2013, which claims priority to EP 12356001.3, filed Feb. 1, 2012; each of which are incorporated by reference in their entireties1. ...

Process for the preparation of 5-fluoro-1H-pyrazoles starting from hexafluoropropene

A new process for the preparation of 5-fluoro-1H-pyrazoles of the general formula (I) as described herein and further reactions with this compound. 11. A process according to claim 1 , wherein Ris methyl.12. A process according to claim 1 , wherein the catalyst in Step 1 and the fluoride donor in Step 2 are identical.13. A process according to claim 1 , wherein the solvent in Step 3 and Step 4 is identical claim 1 , optionally methylene chloride.14. A product comprising hexafluoropropene adapted for the preparation of a compound selected from the group consisting of formula (6) claim 1 , (6a) claim 1 , (7) claim 1 , (7a) claim 1 , (I) claim 1 , (Ia) claim 1 , (II) claim 1 , (IIa) claim 1 , (III) claim 1 , (III′) claim 1 , (IIa) claim 1 , (III″) claim 1 , (III″′) claim 1 , (IIIb) claim 1 , and (IV) comprising the process according to . 5-fluoro-1H-pyrazoles, in particular 5-Fluoro-1-methyl-3-pentafluoroethyl-4-trifluoromethyl-1H-pyrazole, are important building blocks for the preparation of crop protection chemicals, as those described in WO 2010051926, WO 2012/069366, WO 2012/0803876 and WO 2012/107343.For the dimerization of hexafluoropropene (HFP) to perfluoro-4-methyl-2-pentene different catalyst and processes have been used.Perfluoro-2-methyl-2-pentene is commercially available (Fa. Daikin) and P&M Invest (Russia). However, the compound is toxic.Alternatively, it can be prepared via dimerization of hexafluoropropene (see, e.g., U.S. Pat. No. 5,254,774; R. Haszeldiner et al, Journal of the Chemical Society D: Chemical Communications (1970), (21), 1444-1445.DE 4228592 describes the preparation of perfluoro-4-methyl-2-pentene in the presence of N,N,N,N-Tetramethylethylendiamin and Kaliumfluoride.Pazenok et al. describes the preparation of perfluoro-4-methyl-2-pentene in the presence of ammonium and phosphonium perfluorocyclobutane ylides (Pazenok et al., Tetrahedron Letters, (1996), 52(29), 9755-9758).U.S. Pat. No. 5,254,774 describes the preparation of ...

PROCESS FOR PREPARING 5-FLUORO-1-ALKYL-3-FLUOROALKYL-1H-PYRAZOLE-4-CARBALDEHYDE

New method for the preparation of N-methyl-3-difluormethyl-5-fluorpyrazol aldehyde starting from N-methyl-3-haloalkyl-5-chlororpyrazol aldehyde comprising simultaneous fluorination (one step process) of haloalkylgroup in position 3 and replacing haloatom in position 5 by fluorine. 2. A process according to wherein the fluorinating agent is selected from the group consisting of HF claim 1 , HF-Py claim 1 , EtN.3HF claim 1 , Bu3N.3HF claim 1 , HF claim 1 , Dioxane and EtN.3 HF.3. A process according to wherein the fluorinating agent is HF or EtN.3 HF4. A process according to wherein a catalyst selected from the group consisting of ZnF claim 1 , CuF claim 1 , NiFand TiFis present.5. A process according to wherein no catalyst is present.6. A process according to wherein{'sup': '3', 'sub': '2', 'Ris CFHCl or CHCl;'}{'sup': '2', 'sub': '2', 'Ris HCFor HCFCl;'}{'sup': '1', 'sub': 1', '3, 'Rrepresents a C-C-alkyl,'}{'sup': '4', 'Rrepresents H or Cl.'}8. A compound of formula (II) according to wherein{'sup': '3', 'sub': '2', 'Ris CFHCl or CHCl,'}{'sup': '1', 'sub': 1', '3, 'Rrepresents a C-C-alkyl,'}{'sup': '4', 'Rrepresents H.'} The present invention relates to a novel process for preparing 5-fluoro-1-alkyl-3-fluoroalkyl-1H-pyrazole-4-carbaldehyde (I), an useful intermediate in the manufacture of fungicides.Processes for the preparation of 5-fluoro-1,3-dialkyl-1H-pyrazole-4-carbaldehyde by exchanging chlorine for fluorine (halex processes) are known particularly for 5-chloro-1,3-dialkyl-1H-pyrazole-4-carbonyl chlorides (cf. for example WO 2007/031212 and EP-A 0 776 889).It is known from WO 2011/061205 that 5-fluoro-1-alkyl-3-fluoroalkyl-1H-pyrazole-4-carbonyl chlorides can be prepared by reacting in a first step 5-chloro-1-alkyl-3-fluoroalkyl-1H-pyrazole-4-carbaldehyde with metal fluorides like KF as fluorinating reagent to obtain 5-fluoro-1-alkyl-3-fluoroalkyl-1H-pyrazole-4-carbaldehyde, followed by a second reaction with a chlorinating agent to obtain the acyl chloride ...

METHOD FOR PRODUCING SUBSTITUTED ANTHRANILIC ACID DERIVATIVES

The present invention relates to a process for preparing substituted anthranilic acid derivatives of the formula (I) 4. A compound of formula (IV) according to claim 3 , wherein Ris fluorine.5. A compound of formula (IV) according to claim 3 , wherein Ris chlorine.6. A compound of formula (IV) according to claim 3 , wherein Ris CF.7. A compound of formula (IV) according to claim 3 , wherein Ris CF.8. A compound of formula (IV) according to claim 3 , wherein Ris chlorine.9. A compound of formula (IV) according to claim 3 , wherein Ris cyano. This application is a divisional application of U.S. application Ser. No. 14/924,889, filed Oct. 28, 2015, which is a continuation application of U.S. application Ser. No. 14/375,496, filed Jul. 30, 2014, which is a §371 National Stage Application of PCT/EP2013/052350, filed Feb. 6, 2013, which claims priority to European Application No. 12154290.6, filed Feb. 7, 2012, the contents all of which are incorporated herein by reference in their entireties.Field of the InventionThe present invention relates to a novel process for preparing substituted anthranilic acid derivatives of the formula (I)in whichwherein which the R, Rand Rradicals are each as defined above andR—OH   (V)in which Ris as defined above or a compound of the general formula (VI)HNRR  (VI)in which Rand Rare each as defined above.Description of Related ArtThe literature already states that it is possible to obtain substituted anthranilic acid derivatives of the formula (I) by reaction of anthranilic acid derivatives of the general formula (VII)with carboxylic acids of the general formula (VIII)R—COOH   (VIII)in the presence of agents which activate the carboxyl group for the desired reaction, for example thionyl chloride, oxalyl chloride, phosgene, methanesulphonyl chloride or toluenesulphonyl chloride (WO 2003/015519; WO 2003/106427; WO 2004/067528; WO 2006/062978; WO 2008/010897; WO 2008/070158; WO 2008/082502; WO 2009/006061; WO 2009/061991; WO 2009/085816; WO ...

METHOD FOR THE PREPARATION OF PERFLUOROALKYL CONTAINING PYRAZOLES CARBOXYLATES

The present invention pertains to a novel process for the preparation of Fluoroalkylpyrazole- or Bisperfluoroalkypyrazole carboxylates comprising a cyclization of Perfluoroalkyl ketoesters with hydrazines. 3. A fluoroalkylacetoactate according to wherein Ris HCF claim 2 , Ris C-CAlkyl and Ris CF.5. Process according to wherein Ris HCF claim 4 , Ris C-C-Alkyl and Ris CF.7. A haloderivative according to wherein Ris HCF claim 6 , Ris C-C-Alkyl and Ris CF. The present invention pertains to a novel process for the preparation of Fluoroalkylpyrazole- or Bisperfluoroalkypyrazole carboxylates comprising a cyclization of Perfluoroalkyl ketoesters with hydrazines.N-Allyl-3-Perfluoroalkyl-5-Fluoropyrazoles carboxylates are important intermediates for the preparation of agrochemical active ingredients, particularly of fungicides. Correspondingly, N-Alkyl-3-Perfluoroallcyl-5-Fluoropyrazoles carboxylates are described, for example, in the synthesis of fungicidally effective pyrazole carboxamides derivatives (cf e.g. WO 2010/130767), or in the synthesis of fungicidally effective arylalkylpyrazolecarboxamide derivatives and analogues (cf e.g. WO 2011/151370).Usually, 3-Perfluoralkyl-5-Fluoro pyrazoles carboxylates are prepared via multistep transformations starting from acetoacetates. The preparative process of 5-fluoro-1-alkyl-3-fluoroalkyl-1H-pyrazole-4-carbonyl chlorides from 5-chloro-1-alkyl-3-fluoroallcyl-1H-pyrazol-4-carbaldehyde is disclosed in WO 2011/061205.Proceeding from this prior art, the object of the present invention is to provide an improved one step process for the preparation of Fluoroalkylpyrazole- or Bisperfluoroalkypyrazole carboxylates derivatives which can be carried out easily and cost-effectively. The Fluoroalkylpyrazole- or Bisperfluoroalkypyrazole carboxylates obtainable using this desired process should preferably be obtained with high yield and high purity. In particular, the desired process should allow the desired target compounds to be obtained ...

Method for preparing N-(1,3,4-oxadiazol-2-yl)arylcarboxamides

A method for preparing N-(1,3,4-oxadiazol-2-yl)arylcarboxamides of formula (I) is described. 2. Method according to claim 1 , wherein the compound of formula (II) is used with an excess of 10% relative to the compound of formula (III).3. Method according to claim 1 , wherein thionyl chloride claim 1 , phosgene or diphosgene is used as activator.4. Method according to claim 1 , wherein thionyl chloride is used as activator.5. Method according to claim 1 , wherein the activator and the compounds of formula (III) are used in a molar ratio of from 1.2 to 1.9.6. Method according to claim 1 , wherein the base of formula (IV) and the compounds of formula (III) are used in a molar ratio of from 1 to 2.5.7. Method according to claim 1 , wherein the solvent used is tetrahydrofuran claim 1 , acetonitrile claim 1 , 2-methyl-5-ethylpyridine or 3-methylpyridine.8. Method according to claim 1 , wherein the solvent used is 3-methylpyridine.9. Method according to claim 1 , wherein{'sup': '1', 'Ris hydrogen, methyl, ethyl, n-propyl, isopropyl or phenyl,'}{'sup': '2', 'Ris methyl or chlorine,'}{'sup': '3', 'Ris methylsulphenyl, methylsulphinyl or methylsulphonyl,'}{'sup': '4', 'Ris trifluoromethyl,'}{'sup': '5', 'Ris methyl or n-butyl.'}10. Method according to claim 1 , wherein{'sup': '1', 'Ris methyl,'}{'sup': '2', 'Ris methyl or chlorine,'}{'sup': '3', 'Ris methylsulphonyl,'}{'sup': '4', 'Ris trifluoromethyl,'}{'sup': '5', 'Ris methyl.'}11. Method according to claim 1 , wherein the reaction is conducted in a range of 0° C. to 25° C. The invention relates to a method for preparing herbicidally active N-(1,3,4-oxadiazol-2-yl)arylcarboxamides.WO 2012/126932 A1 discloses herbicidally active N-(1,3,4-oxadiazol-2-yl)arylcarboxamides. A method for their preparation is also described therein. In this method, substituted benzoic acids are reacted with 2-amino-1,3,4-oxadiazoles, which are substituted in the 5-position, in the presence of activating reagents such as carbonylimidazole (CDI), ...

PROCESS FOR THE PREPARATION OF 5-FLUORO-1H-PYRAZOLES

A new process for the preparation of 5-fluoro-1H-pyrazoles of the general formula (I) as described herein, resulting from the reaction of an olefin with hydrazine in the presence of water and a base. 2. Process according to claim 1 , wherein{'sup': '1', 'Ris methyl'}{'sup': '2', 'sub': '3', 'Ris CF'}{'sup': '3', 'sub': 2', '5, 'Ris CF.'}3. Process according to claim 1 , wherein the base is triethylamine.5. Process according to claim 4 , wherein{'sup': '2', 'Ris trifluoromethyl,'}{'sup': '3', 'Rpentafluoromethyl,'}{'sub': '3', 'sup': '+', 'and wherein Kat is (HNAlkyl).'}7. Process according to claim 6 , wherein a compound of formula (IV) is a compound of formula (II) claim 6 , optionally of formula (II′).8. Process according to claim 6 , wherein a compound of formula (IV) is compound (IIa).11. Process according to claim 10 , wherein a compound of formula (III) is compound of formula (III′) claim 10 , optionally compound (IIIa) or compound (IIIb).13. Process according to claim 6 , wherein a compound of formula (IV) is a compound of formula (III″) claim 6 , optionally of formula (III″).15. Process according to claim 1 , wherein Ris methyl. 5-fluoro-1H-pyrazoles, in particular 5-Fluoro-1-methyl-3-pentafluoroethyl-4-trifluoromethyl-1H-pyrazole, are important building blocks for the preparation of crop protection chemicals, as those described in WO 2010051926.It is known that 5-fluoro-1-methyl-3-pentafluoroethyl-4-trifluoromethyl-1H-pyrazole can be prepared by the treatment of the dimer of hexafluoropropene with water free N,N-dimethylhydrazine in diethyl ether at −50° C. followed by heating of the intermediate at 120° C., I. L. Knunyants et al. Izv. Akad. Nauk SSSR, (1990) 2583-2589.However, this two step transformation requires low temperatures for the first step and results in the formation of CHF during the thermal elimination in the second step, making this process expensive, environmentally unfriendly, and particularly difficult for industrialization.Starting from ...

PROCESS FOR THE PREPARATION OF 5-FLUORO-1H-PYRAZOLES

A new process for the preparation of 5-fluoro-1H-pyrazoles of the general formula (I) as described herein comprising reacting an olefin with an hydrazine. 2. Process according to claim 1 , wherein the nucleophile is selected from alcohols claim 1 , thioles or secondary amines claim 1 , and in case the nucleophile is an alcohol or a thiol claim 1 , also in the presence of a base.3. Process according to claim 1 , wherein{'sup': '1', 'Ris methyl'}{'sup': '2', 'sub': '3', 'Ris CF'}{'sup': '3', 'sub': 2', '5, 'Ris CF,'}4. Process according to claim 1 , wherein the nucleophile is methanol and the base is triethylamine.6. Process according to claim 5 , wherein a compound of formula (IV) is a compound of formula (II) claim 5 , optionally of formula (II′).7. Process according to claim 5 , wherein a compound of formula (IV) is compound (IIa).10. Process according to claim 9 , wherein a compound of formula (III) is compound of formula (III′) claim 9 , optionally compound (IIIa) or compound (IIIb).12. Process according to claim 5 , wherein a compound of formula (IV) is a compound of formula (III″) claim 5 , optionally of formula (III′″).14. Process according to claim 1 , wherein Ris methyl. 5-fluoro-1H-pyrazoles, in particular 5-Fluoro-1-methyl-3-pentafluoroethyl-4-trifluoromethyl-1H-pyrazole, are important building blocks for the preparation of crop protection chemicals, as those described in WO 2010051926.It is known that 5-fluoro-1-methyl-3-pentafluoroethyl-4-trifluoromethyl-1H-pyrazole can be prepared by the treatment of the dimer of hexafluoropropene with water free N,N-dimethylhydrazine in diethyl ether at −50° C. followed by heating of the intermediate at 120° C., I. L. Knunyants et al. Izv. Akad. Nauk SSSR, (1990) 2583-2589.However, this two step transformation requires low temperatures for the first step and results in the formation of CHF during the thermal elimination in the second step, making this process expensive, environmentally unfriendly, and particularly ...

FUNGICIDE PYRAZOLE CARBOXAMIDES DERIVATIVES

The present invention relates to pyrazole carboxamides derivatives of formula (1) wherein Y represents CRor N, T represents S or O, X1 and X2 represent a chlorine or a fluorine atom, and Z1 represents a substituted or non-substituted cyclopropyl; Their process of preparation, their use as fungicide, and/or anti-mycotoxin active agents, and/or insecticide, and/or nematicide, particularly in the form of fungicide compositions, and methods for the control of phytopathogenic fungi, notably of plants, using these compounds or compositions. 122-. (canceled)24. The method of wherein wherein Y is CR.25. The method of wherein Y is nitrogen.26. The method of wherein T is oxygen.27. The method of wherein Xis a fluorine atom.28. The method of wherein Xis a fluorine atom.29. The method of wherein Zis a non substituted cyclopropyl.30. The method of wherein Zand Zare independently selected from the group consisting of hydrogen atom and methyl.31. The method of wherein Zis hydrogen.32. The method of wherein R claim 23 , R claim 23 , R claim 23 , Rand Rare independently selected from the group consisting of hydrogen; halogen; substituted or non substituted C-C-alkyl; C-C-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C-C-cycloalkyl; tri(C-C-alkyl)silyl; and substituted or non substituted C-C-alkylsulfanyl.33. The method of wherein Ris selected from the group consisting of halogen; C-C-alkyl; C-C-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C-C-cycloalkyl; tri(C-C-alkyl)silyl; and C-C-halogenoalkylsulfanyl comprising up to 9 halogen atoms which can be the same or different.34. The method of wherein Rand Rare independently selected from the group consisting of halogen; C-C-alkyl; C-C-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C-C-cycloalkyl; tri(C-C-alkyl)silyl; and C-C-halogenoalkylsulfanyl comprising up to 9 halogen atoms which can be the ...

PROCESS FOR PREPARING 2,2-DIFLUOROETHYLAMINE DERIVATIVES BY ALKYLATING 2,2-DIFLUOROETHYLAMINE

A method for preparing a 2,2-difluoroethylamine of the formula (III) in which 2,2-difluoroethylamine of the formula (I) is reacted with a halide of the formula (II) in the presence of a tertiary nitrogen base: 2. Method according to claim 1 , in which the molar ratio of diisopropylethylamine to the halide of the formula (II) used is in the range from 10 to 0.5.3. Method according to claim 1 , in which the molar ratio of halide of the formula (II) to the 2 claim 1 ,2-difluoroethylamine used is in the range from approximately 1:1.5 to approximately 1:20.4. Method according to claim 1 , in which claim 1 , after completion of the method claim 1 , diisopropylethylamine and the 2 claim 1 ,2-difluoroethylamine present in excess are removed and are fed again into the method.5. Method according to claim 1 , with which N-[(6-chloropyridin-3-yl)methyl]-2 claim 1 ,2-difluoroethan- 1-amine of the formula (III) is prepared claim 1 , in which 2-chloro-(5-chloromethyl)pyridine is used as halide of the formula (II). The present invention relates to a method (process) for preparing certain 2,2-difluoroethylamine derivatives starting from 2,2-difluoroethylamine.2,2-Difluoroethylamine derivatives are useful intermediates for preparing active agrochemical ingredients (see WO 2007/115644). Various methods for preparing 2,2-difluoroethylamine derivatives known.WO 2009/036900, for example, describes a method for preparing 2,2-difluoroethylamine derivatives by amide hydrogenation of N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroacetamide (scheme 1).This method is unfavourable due to the use of complex hydrides such as sodium borohydride, since hydrides are expensive to use and raise safety concerns.WO 2009/036901 describes the reduction of N-(6-chloropyridin-3-yl)methylene-2,2-difluoroethanamine by hydrogen (scheme 2).This method is unfavourable due to the use of hydrogen, since the use of hydrogen raises considerable safety concerns here to.WO 2011/157650 describes the preparation of 2,2- ...

Method for producing 4-aminobut-2-enolides

Disclosed is a method for producing 4-aminobut-2-enolide compounds of general formula (I), characterized in that compounds of general formula (II) are reacted with amines of general formula (III).

Method for the regioselective synthesis of 1-alkyl-3-haloalkyl pyroazole-4-carboxylic acid derivatives

The present invention relates to a regioselective synthesis of 1-alkyl-3-haloalkyl-pyrazole-4-carboxylic acid derivatives by the cychzation of 2,3-disubstituted acrylic acid derivatives, and the hydrazones created as a by-product in the method.

Processo para a preparação de 1,1,1,4,4,4-hexafluorbuteno-2

Processo para a preparação de 1,1,1,3,3-pentafluorpropano

processo para preparar ditiina-tetracarboxi-diimidas

processo para preparar ditiina-tetracarboxi-diimidas. a presente invenção se refere a um novo processo para preparar ditiina-tetracarboxidiimidas.

Process for the production of chlorofluorobutene

PROCESS FOR BIARIL PRODUCTION

Method for the production of 2,2-difluoroethylamine

Method for manufacturing 4-aminobut-2-enolids

Preparation of 4-aminobut-2-enolide compound (I) comprises: either reacting 4-haloacetic ester (II) with an amine compound (IIIa) to give a haloalkene ester compound (IVa); thermally cyclizing (IVa) in the presence of a solvent to give 4-amino-5H-furan-2-one compound (Va); and reacting (Va) with an alkyl compound (VIa); or reacting (II) with an alkane amine compound (IIIb) to give (IVb); thermally cyclizing (IVb) in the presence of a solvent to give 4-amino-5H-furan-2-one compound (Vb) and reacting (Vb) with an alkyl compound (VIc). Preparation of 4-aminobut-2-enolide compound of formula (I) comprises: either reacting 4-haloacetic ester of formula (Hal-CH 2-C(=O)-CH 2-C(=O)-O-R 2>) (II) with an amine compound of formula (NH 2R 1>) (IIIa) to give haloalkene ester compound of formula (Hal-CH 2-C(NH(R 1>))=CH-C(=O)-O-R 2>) (IVa); thermally cyclizing (IVa) in the presence of a solvent to give 4-amino-5H-furan-2-one compound of formula (Va); and reacting (Va) with an alkyl compound of formula (A-CH 2-L) (VIa); or reacting (II) with an alkane amine compound of formula (NH 2-CH 2-A) (IIIb) to give (IVb); thermally cyclizing (IVb) in the presence of a solvent to give 4-amino-5H-furan-2-one compound of formula (Vb) and reacting (Vb) with an alkyl compound of formula (R 1>-L) (VIc). A : pyrid-2-yl, pyrid-4-yl or pyrid-3-yl (all optionally substituted by F, Cl, Br, CH 3, CF 3or CF 3O (at sixth position)), pyridazin-3-yl (optionally substituted by Cl or CH 3(at sixth position)), pyrazin-3-yl, 2-chloropyrazin-5-yl or 1,3-thiazol-5-yl (all optionally substituted by Cl or CH 3(at second position)), pyrimidinyl, pyrazolyl, thiophenyl, oxazolyl, isoxazolyl, 1,2,4-oxadiazolyl, isothiazolyl, 1,2,4-triazolyl or 1,2,5-thiadiazolyl (all optionally substituted by F, Cl, Br, CN or NO 2) or 1-4C-alkyl, 1-3C-alkylthio or 1-3C-alkylsulfonyl (all optionally substituted by F and/or Cl) or a substituted pyridine moiety of formula (A1); X : halo, alkyl or haloalkyl; Y 1> : halo, ...

3-triazolylphenyl-substituted sulfide derivatives for use as acaricides and insecticides

The present invention relates to novel 3-triazolylphenyl-substituted sulfide derivatives of formula (I), wherein A 1 , A 2 , B 0 , B 1 , B 2 , B 3 , X, R 1 , R 2 and n are defined as in the description, to their use as acaricides and insecticides for the control of animal pests and to methods for producing the same.

3-[1-(3-haloalkyl)-triazolyl]-phenyl-sulfide derivatives for use as acaricides and insecticides

The present invention relates to novel 3-[1-(3-haloalkyl)-triazolyl]-phenyl-sulfide derivatives of formula (I), wherein A 1 , A 2 , B 0 , B 1 , B 2 , B 3 , R 1 , R 2 and n are defined as in the description, to their use as acaricides and insecticides for the control of animal pests and to methods for producing the same.

Novel solid form of 4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5h)-one

The invention relates to a novel solid form of 4-[[(6-Chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5H)-one, to a method for the production of same, and to the use of same in agrochemical preparations.

Method for producing enaminocarbonyl compounds

The present invention relates to a process for preparing enaminocarbonyl compounds by reacting compounds of the formula (II) with compounds of the formula (III) in which the A, R 1 , R 2 and Z radicals are each as defined in the description, in the presence of a Brønsted acid.

Novel process for preparing enaminocarbonyl compounds

Novel method for producing enaminocarbonyl compounds

The invention relates to a method for producing enaminocarbonyl compounds of formula (I), according to which compounds of formula (II) are reacted in the presence of a Brønsted acid to form compounds of formula (I) and A, R 1 and Z are defined as cited in the description. The invention also relates to corresponding parent compounds that are used in the claimed method.

Novel method for producing enaminocarbonyl compounds

Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von Enaminocarbonylverbindungen wobei Verbindungen der Formel (II) mit Verbindungen der Formel (III) worin die Reste A, R 1 , R 2 und Z die in der Beschreibung aufgeführten Bedeutungen haben, in Gegenwart einer Bransted-Säure umgesetzt werden.

Novel method for producing 4-aminobut-2-enolides

The invention relates to a method for producing 4-aminobut-2-enolide compounds of the formula (I), comprising the reaction of a 4-(methylamino)furane-2-(5H)-one compound of the formula (II) with an amine of the formula (III), where R1 and A have the definitions mentioned in the description, optionally in the presence of a Bronsted acid.

Novel method for producing 4-aminobut-2-enolides starting from 4-alkoxyfuran-2(5h)-on or 4-arylalkoxyfuran-2-(5h)-on

The invention relates to a method for producing 4-aminobut-2-enolide compounds of the formula (I), comprising: converting a 4-alkoxyfuran-2(5H)-on compound or 4-arylalkoxyfuran-2(5H)-on compound of the formula (II) and an amine of the formula (III), where R 1 , R 2 , and A have the definitions indicated in the description, in the presence of a Brønstedt acid.

Process for preparing 2,2-difluoroethylamine derivatives by alkylation with 2,2-difluoro-1-haloethanes

A process for preparing 2,2-difluoroethylamine derivatives of the general formula (III) in which A is an optionally substituted heterocycle as described in the description, in which a 2,2-difluoroethyl-1-haloethane compound of the general formula (I) in which Hal is Cl, Br or iodine is reacted with an amine of the general formula (II) in which A is as defined above, optionally in the presence of a base.

Method for preparing 2,2-difluoroethylamine derivatives starting from n-(2,2-difluoroethyl)prop-2-en-1-amine

A method for preparing 2,2-difluoroethylamine derivatives of formula (IV) comprises steps (i) and (ii). In step (i), N-(2,2-difluoroethyl)prop-2-en-1-amine of formula (I) is reacted with a compound of formula (II) A-CH 2 -E to form a compound of formula (III), optionally in the presence of an inorganic or organic base. In step (ii), the allyl group is removed (deallylation) from the compound of formula (III), A and E in formulae (II), (III) and (IV) having the meanings indicated in the description.

Process for preparing 2,2-difluoroethylamine derivatives by alkylating 2,2-difluoroethylamine

A process for preparing a 2,2-difluoroethylamine of the formula (III), in which 2,2-difluoroethylamine of the formula (I) is reacted with a halide of the formula (II) in the presence of a tertiary nitrogen base: in which Hal and A in the formulae (II) and (III) are defined as specified in the description.

Method for producing 2,2 difluoroethylamine derivatives by imine hydrogenation

The invention relates to a method for producing 2,2 difluoroethylamine derivatives, wherein compounds of the general formula (IV) are hydrogenated to form the corresponding 2,2 difluoroethylamine derivatives of the general formula (III) and the groups A, R 1 and R 2 have the meanings indicated in the description.

Process for the preparation of 4-aminobut-2-enolides

Process for the preparation of 4-aminobut-2-enolide compounds of the formula (I): comprising reaction of a 4-(methylamino)furan-2(5H)-one compound of the formula (II) with an amine of the formula (III) in which R 1 and A have the definitions mentioned in the description, optionally in the presence of a Brønstedt acid.

Process for the preparation of 4-aminobut-2-enolides starting from 4-alkoxyfuran-2(5H)-one or 4-arylalkoxyfuran-2(5H)-one

Process for the preparation of 4-aminobut-2-enolide compounds of the formula (I): comprising reaction of a 4-alkoxyfuran-2(5H)-one compound or 4-arylalkoxyfuran-2(5H)-one compound of the formula (II) with an amine of the formula (III) in which R 1 , R 2 and A have the definitions given in the description, in the presence of a Brønstedt acid.

New method of producing 4-aminobut-2-enolides starting from 4-alkoxyfuran-2(5H)-one or 4-arylalkoxyfuran-2-(5H)-one

Process for preparing 2,2-difluoroethylamine derivatives by alkylation with 2,2-difluoro-1-haloethanes

Process for preparing 2,2-difluoroethylamine derivatives by alkylating 2,2-difluoroethylamine

A method for preparing a 2,2-difluoroethylamine of the formula (III) in which 2,2-difluoroethylamine of the formula (I) is reacted with a halide of the formula (II) in the presence of a tertiary nitrogen base: where, in the formulae (II) and (III), Hal and A are defined as stated in the description.

A method for producing alkenyl nitrobenzol derivatives unbranched in the 1-position

Die vorliegende Erfindung betrifft ein Verfahren zum Herstellen von Alkenylnitrobenzolen und Alkylanilinen, die als Zwischenprodukte für fungizid wirksame Alkylaniliden Bedeutung haben.

Process for preparing 3-dihalomethylpyrazole-4-carboxylic acid derivatives

The invention relates to a process for preparing 3-dihalomethylpyrazole-4-carboxylic acid derivatives of the formula (I) by reacting α-fluoroamines of the formula (III), in the presence of Lewis acids, with acrylic acid derivatives of the formula (II) to give vinamidinium salts of the formula (IV) and subsequently reacting them with hydrazines, and to the vinamidinium salts of the formula (IV) themselves.

Method for producing pyrazolylcarboxanilides

The invention relates to a simplified method for producing pyrazolylcarboxanilides by reacting pyrazolyl carboxylic acid esters with anilines in the presence of a base and removing at least one reaction product.

Process for preparing 3-dihalomethyl-pyrazole-4-carboxylic acid derivatives

The invention relates to a process for preparing 3-dihalomethylpyrazole-4-carboxylic acid derivatives of the formula (I) by reacting α-fluoroamines of the formula (III) in the presence of Lewis acids with acrylic acid derivatives of the formula (II) to give vinamidinium salts of the formula (IV) and the subsequent reaction thereof with hydrazines, and to the vinamidinium salts of the formula (IV) themselves.