COMPOSITION FOR CONTROLLING UNDESIRED PLANTS
The invention concerns means for the fight against unwanted plants, thereby characterized that it as an effective component a connection of the general formula OCH2C1 acre-n, (i) contained where acre one by one or more substituents of the row halogen, c1 _4 alkyl, c1,4 Alkoxy, C1.4AlkyI'S, c1,4 AlkyI THEN, C2 _4 - Alkanoyl, C (=NOCI_4AIkyl) - CI_3 alkyl, C (OCI_4 alkyl) 2 - CI_3 alkyl, and c1 _5 Alkoxy earbonyl substituted hetero flavour ashes group of the row Thien-3-yl, Furan-3-yl, Pyrrol-3-yl, Isoxazol-4-yl, Isothiazol.4-yl and Pyrazol-4-yl means, and ffir a hydrocarbon selected from the row C3_8Alkenyl and C3.8Alkinyl, stands for Y, unsubstituiert or by halogen, selected from the row F, c1 or Br, substituted is; or for by F, CI or Br subsfituiertes c1,8 alkyl stands; or a group of CHR1 - COY1 means, in which g 1 stands for II or c1,5 alkyl, and Y1 Hydroxy, c1 _5Alkoxy, C3_5 Alkinyloxy, c1 _4 Alkylamino, Di. (C1 -4Alkyl) amino or NI-I-N--C (C1-3) alkyl) 2 means, or a group of R2 - Az meant, in which R2 for unsubstituiertes or by c1 _5Alkyl substituted CH2 or CH2 - CH2 stands, and selected 3,5-Dimethyl-l-pyrazolyl, 1,2,4-Triazolyl, 2-Pyrimidinyl means Az an heteroaromatic ring from 1-Pyrazolyl, or from one by or two substituents of the row CI_4Alkyl or c1 _4 Alkylthio subsütuierten if necessary Furyl, Thienyl, Thiazolyl, Isoxazolyl, 1,3,4-Oxadiazolyl, 1,2,4-Oxadiazolyl, 1,3,4-Thiadiazolyloder 1,3,4-Triazolylring, or a group of A-OR3 meant, where R3 means,4 Alkoxy substituted c1 .8Alkyl, and A a unsubstituierten or hydrocarbon remainder monosubstituted by c1 _5 Alkoxy for I-1 or for if necessary by halogen, CN, or c1, which can be linked with R3, under formation of a 1,3-Dioxoplanringes, whereby the Nund of O-atoms, which are connected by means of A, is through up to 3 carbon atoms from each other separated; or a group of CHR5 - CHR5 “=NOR4 where R4 c1. ,4 alkyl and R5 and R5” independently H or CH3, means.
A suitable meaning of A-O-R3, if A is linked to a ring with R3, e.g. is. 1,3-Dioxolan2-yl-C1_3alkylen.
If A is not linked to a ring with R3, A means in particular an non-aromatic, in particular a c1 _sAlkylen-Gruppe those the Ound N-atom at those it is bound with 1 to 3, in particular 1 to 2 carbon atoms separates. A suitable meaning of A is e.g. the CH2 or CH2-Ct-I2 group as well as monomethylierte derivatives of it, in particular CH2, CH (CH3), CH2 CH2, CH (CH3) CH2; R3 is then in particular c1 _3 alkyl such as CH3, C2 H5 and _nC3 H7.
Connections formula I can for example received, by one a Chloracetamid of of the general formula ArNH - COCH2 CI, (III) where acre above meaning possesses, with a connection of of the general formula LY, (1V) where Y possesses above meaning and a group split offable under the conditions of a N-Alkylierungsreaktion means L, converts No. 391,791 above procedure can similarly to well-known procedures, after for the N-alkylation of amides admitted methods to be accomplished. The conversion becomes appropriately in solvents inert on the reaction conditions, e.g. Dimethoxyäthan or acetonitrile, or accomplished in an aqueous/organic Zweiphasensystem in presence of a phase transfer catalyst.
Suitable meanings of L (in the formula IV) are c1, Br or the Sulfonyloxyrest of an organic sulfone acid such as Mesyloxy or p-Tosyloxy.
The connections of the formula III are preferably used in particular in Salzform, in alkali metal salt form, e.g. in well salt form. Such salts can being received to an alkali metal amide, a hydride, - hydroxide or - alcoholate on well-known way by conversion a connection of the formula III with a base like.
The connections of the formula I can be isolated and regenerated after well-known way from the reaction mixture.
The connections of the formula I therefore possess in or several asymmetrical centers and can in optically active, diastoreomeren, racemischen or geometrical isomers formula exist. Generally such connections are used as mixture in accordance with the invention, even if isolating can take place similar to well-known methods.
The connections of the formula 111 become by N-Acyliernng of an amine of the general formula acre NI-I2, (V) where acre above meaning possesses, with chlorine acetyl chloride receives.
If the production of the parent compounds is not descriptive, these are well-known or can them similarly to well-known and/or herein descriptive methods manufactured and be cleaned.
The invention-measured means possess herbicides effect, whereby herbicide is to be understood here in general sense, when a means permits a growth inhibition or a growth influence of plants. With plants are meant germinating seeds, Keimlinge and established Vegetaäon including underground parts.
The valuable herbicides effect of the according to invention of the means comes out e.g. from the damage, which with test quantities from 1.4 to 5,6 kg of a connection of of the general formula (I)/ha after preoder post office cm application (Voroder Nachauflauf) with monound dicotylen plants such as Lepidium sativum, Avena sativa, Agrostis alba and Lolium perenne to be observed. Due to this herbicides effect the erfindnngsgemäßen connections come with the fight against dikotylen or monokotylen weeds into consideration, like this by supplementing regulations with representative connections are confirmed with test quantities according to an application quantity from 0.2 to 5,0 kg (e.g. 0.2, 1,0 and 5,0 kg) per ha of a connection of the general formula (I) on dikotylen weeds such as Amaranthus retroflexus, Capsella bursa pastoris, Chenopodium alba, Stellaria media, Senecio vulgaris, Galium aparine, and on grasses such as Agropyron repens, Agrostis alba, Alopecurus of myosuroides, Apera spica Venti, arena fatua, Echinochloa crus galli, Bromus tectorum, sorghum halepense, Digitaria spp and Setaria spp. Supplementing attempts show a favorable ground resistance of the means according to invention.
Those means are less toxic according to invention against useful plants than against Unkrauter. The selective herbicides effect e.g. in corn, soy, cotton, sugar beets, potatoes, Alfalfa, sunflowers, rape, is observed Erdnüßehen and flax depending upon used substance and application quantity. The means according to invention are suitable therefore also for the use as selective herbicides in useful plants.
The means according to invention know and will favourably together with for herbicides acceptable solvent used. Suitable means contain 0,01 to 99 of weight % at active substance, 0 to 20% surface-active materials and 1 to 99,99%, acceptable for herbicides, of a firm or liquid solvent. Higher conditions surface-active materials: Active substance are sometimes desired and fulfilled by including into the preparation or in tank-mix. Application forms of the means according to invention contain generally 0,01 to 25 weight % at active substance.
Smaller quantities of active substance can be naturally present, depending upon intended application and physical characteristics of the active substance. Concentrated preparation forms, which are diluted before application, preferably contains 2 to 90 weight % 10 to 80 weight % at active substance.
Examples of suitable means in accordance with the invention cover types of dust means, granulates, pellets, suspension concentrates, Spritzpulver (wettable powders), Emalsionskonzentmte etc. you according to well-known methods, e.g. by mixture of a connection of the general formula 0) with Verdännern will receive. Liquid preparations will receive e.g. by mixing the components, fine-grained firm Znbereitungen by mixing and grinding, suspension concentrates through to wet meals and granulates and PeUets by impregnating or coating submitted carriers with active substance or by Agglomerationsteehniken (fluidized bed e.g.).
The erfmdnngsgemäßen means can be present also in the form of micro caps.
For herbicides acceptable Addifive can be used likewise in the herbicides preparations e.g.
in order to improve the effect and over foams to avoid a sticking and corrosion.
The term surface-active materials, how herein uses, means everyone for I-Ierbizide acceptable material, No. 391,791 the emulsiveness, wettability and dispersion ability lends and/or the improvement of other surface properties like e.g. Propagation and adhesion on plant parts cause.
Examples of such surface-active materials are Natriumligninsnlfonat and Laurylsulfat.
The term solvent, how herein uses, means a liquid or firm material acceptable for herbicides, which is used, in order to dilute the active substance to an useful or desired form. For types of dust means or granulates e.g. is this. Talc, kaolin or Diatomeenerde, for liquid concentrated formula e.g. a hydrocarbon such as XyloI or an alcohol such as isopropanol, and for liquid application forms z.
B. Water or diesel oil.
The erfindnngsgemäßen preparations can contain also different materials, which possess biological effect, like e.g. Connections with änhlicher or complementary herbizider effect or connection with antagonistic, fungicidal or insektizider effect.
In the following specific examples of herbizider preparations are described. (Parts are parts by weight).
Example A: Spritzpulver of parts of a connection of the general formula (I), e.g. the connection No. 19 (table A), 25 parts fine, synthetic silicate, 2 parts of Natrinmlaurylsulfat, 3 parts of Natriumligninsulfonat and 45 parts finely distributed Kaolinit so for a long time and husbands to the middle Teilchengröl3e approx. 5 Micron is mixed is. The received Spritzpnlver before application with water diluted to a Spritzbrühe with desired concentration.
Example B: Emulsion concentrate of parts of a connection of the general formula (I), e.g. the connection No. 19 (table A), 40 parts xylene, 30 parts dimethylformamide and 10 parts of an emulsifying agent (e.g. ATLOX 4851 B, a mixture of approx.-Alkylarylsulfonat and polyäthoxyliertem Triglycerid the Atlas chemistry GmbH) strongly mixed to a homogeneous liquid received is. In such a way received emulsion concentrate is diluted before use with water.
Example C: Granulates 5 kg of a connection of the general formula (I), e.g. the connection No. 19 (table A) in 25 I CH2C12 are solved. The solution is then given and mixed to Attapulgit of the Körnnng 24/48 to 95 kg mesh/inches. The solvent is removed under decreased pressure.
In the following ii-production regulations procedures for the production of connections of the general formula (I) become described, which can find as active substance in the means according to invention use.
Manufacture regulation 1: N-Chloracetyl-n (2-¢arbomethoxy-4-methyl-thien-3-yl) - Al of inthyles! r 9,9 g (0,04 mol) n (2-Carbomethoxy-4-methyl-thien-3-yl) - chloracetamid portionenweise to a well agitated suspension by 1.5 g (0,05 MoI) close (80% - ige dispersion in mineral oil) in 250 trocknere Dimethoxyethan (DME) are given.
After terminated addition the remaining solution of the well salt still another additional hour with 50° agitated, then left untouched, until it on ambient temperature is cooled down, and afterwards with a solution of 7.25 g (0,04 mol) Ethyl-2-bromopropionat into 50 ml trocknere DME treats.
After one reaction period of 4 hours with 50° the mixture is filtered and evaporated in the vacuum (50°/0,013 mbar). The remaining brown oil becomes, after chromatography at silicagel (eluiert with Diethyläther I Iexan 2: 1) a ball tubing distillation subjected, whereby the analytically pure title connection, Sdp. 135°/0,0065 mbar is received.
Herstellungsv9r hdft 2; N (1H-Pyr4z01-1-ylmethyl) - n (2,4-dimethyl-thien-3-yl) - chloracetamid to a well agitated mixture of 19.35 g (0,095 mol) n (2,4-Dimethyl-thien-3-yl) ehloracetamid, 4,15 g (0,01 mol) Benzyldimethylhexadecyl ammoninmchlorid, 40 g (1 mol) NaOI i, 200 ml CH2 CI2 and 40 ml I-I20 are given in such a manner 17 g (0,11 mol) firm 1-Chlormethyl-pyrazol-hydrochlorid that the temperature does not exceed the 25°.
After terminated addition the reaction mixture is agitated during 2 1/2 hours at ambient temperature. Then 100 ml I-I2 0 are admitted. The organic phase is washed separated, with 3,200 ml Porüonen water, evaporated dried over Na2SO4 and to dry ones. The arrears are ehromatographiert at silicagel. Eluiernng with I-Iexan-Diethyläther 1: 1 supplies the analytically pure title connection in form of a syrup, crystallized after cooling over night on -20°, stop. 88-89° (crystallization in Diethyläther).
No. 391,791 H¢r ellun vorschdft 3: N (chlorine acetyl) - n (3.5-dimethyl-isoxazoi-4-yl) - alanine ethyl esters 9,4 g (0,05 mol) n (3,5-Dimethylisoxazol-4-yl) chloracetamid into 150 ml trocknere CH3CN are dripped to one (80% dispersion in mineral oil) into 25 ml trocknere CH3 CN.
After completion the exotherms of the reaction (34°) the solution of the salt is left untouched, until it on ambient temperature is cooled down, and then with 9.05 g (0,05 mol) ethyl 2-brompropionat in 25 ml dry CH3CN treats.
After terminated addition the reaction mixture is heated up during 3 hours on 50* and evaporated then to dry ones. The arrears are taken up to 100 ml Diethylltther and the solution is filtered. After evaporation of the filtrate remains an oil, which is chromatographiert at silicagel. Eluierung with DiethylätherHexan 1:1 results in the title connection of the Smp. 49-50°.
The following connections of the formula I are kept similar to in the HersteUungsvorschriften 1 to 3 described the procedure: (ME is CH3; Et is C2 H5).
TABLE A connection aryl Y characterisation No.
1 4-Me-thien-3-yl CH2 OC2 H5 Smp. 25-26* 2 “CH2 CH2 OCH3 Rf = - 0,45 (cyclohexane/ethyl acetate 1: 1) 3 2-Me-thien-3-yl CH2 CH2 OCH3 Rf = 0,3 (Cyelohexun/Ethylacetat 6: 4) 4 2,4-diMe-thien-3-yl CH2 C (CH3 ---CH2 Smp. 85-86°” CH2 - C.r. --CH Smp. 95-96° 6 “CH2 CF3 stop. 60-61” 7” CH2 - C (c1) =CH2 stop. 59-61° 8 “CH2 - C (Br)--CH2 stop. 45-46° 9” CHTCOOH Smp. 145..48° “CH2 COOMe stop. 48-49° 11” CH2 COOEt nD20 = 1,5345 12 “CH2 COOC3H7i Sdp. 118-21” /0.0065 mbar of 13” CH2 - COOC (CH3) 2 CaCH Smp. 77-79* 14 “CH (CH3) COOCH3 nD20= 1,5342” CH (CH3) COOC3H7 i nD20= 1,5192 16 “CH2 CON (CH3) 2 Smp. 82-84” 17” CH2 CONHC3 HTi stop. 135-137° 18 “CH2 CONHN--C (CH3) 2 Smp. 141° 19” CH2 (1-pyrazolyl) Smp. 88-89° “CH (CH3) (1-pyrazolyl) stop. 76-78° 21” CH2 - (3,5-diMe-pyrazolyl-1) stop. 143-144 " 22 “CH (CH3) - I N Smp. 132-133” 23” CH2 (2-furyl) Smp. 78-79° 24 “CH2 - (2-thienyl) Smp. 57-59*” CI.12. W. -- Stop. 66-67° ME 26 “3-Me-isoxazol-5-yl-CH2 stop. 77-780 connection No.
27 28 29 31 32 33 34 36 37 38 39 41 42 43 44 46 47 aryl 2,4-diMe-thien-3-yl it 11 it tt It IL IL 11 It 1! IL IL It No. 391,791 TABLE A (continuation) Y characterisation stop. 54-56° Smp. 71-72° Smp. 110-15° N-N N--N CH ù'JL ME Smp. 119-25° Smp. 120-22° Smp. 68-70° CH2OEt CH2OCH7n CH2OC4H9n CH (ME) OMe CH (Et) OMe CH2CH2OMe CH2CH2OEt CH2CH203H7n CH (ME) CH2OMe CH (ME) OCH2 CH2 CI CI-I (OMe) CH2OMe CH2OCH2CH2OMe CH (ME) OCR2C 2CN CH2-CH=NOMe Smp. 115°/0,0013 mbar of nD20 = 1,5280 Sdp. 110-11°/0,0013 mbar of Smp. 48--50° stop. 55-57° stop. 54-55° Sdp. 110°/0,013 mbar of Rf = 0,36 (Diethyläther/hexane 1: 1) Sdp. 148-I50°/0,04 mbar of Smp. 76-78° Smp. 62-64° Rf = 0,3 (Diethyläther/hexane 1: 1) Sdp. 117-18°/0,0065 mbar stop. 59-64° Rf = 0,31 (hexane/ethyl acetate 3: 2) No. 391,791 TABLE A continuation connection No.
Aryl Y Charaktedsierung 48 2,4-diMe-thien-3-yl CH2 - CH=NOEt 49 “CHTC (ME) =NOMe” CH2 - C (ME)--NOEt 51 “CI-I (ME) CI-I=NOMe 52” Ctt (ME) CH=NOEt 53 2-Me-4-Et-thien-3-yl CH (ME) CH2 OMe 54 “CH2 OEt” Pyrazolyl-l-CH2 56 2-Et-4-Me-thien-3-yl CH2 OC2H5 57 “CH (ME) CH2 OMe 58 2,4-diEt-thien-3-yl Pyrazolyl-I-CH2 59” CH2 - OEt “CI-I2CI-I2 OMe 61 2-Me-4-MeO-thien-3-yl Pyrazolyl1-CH2 62” CI-I2-OEt 63 “CH2 CH2 - OEt 64 2-Me-4-EtO-thien-3-yl Pyrazolyl-l-CH2 2-Me-4-nC4 H9 0-thien-3-yl CI-I2 OEt 66 2-MeS-4-Me-thien-3-yl Pymzolyl-l-CH2 67” CH2OEt 68 “CH2CH2 OMe 69 2-MeS (O) - 4-Me-thien-3-yl CH2OEt 2-Meso-4-Me-thien-3-yl CI-I2 OEt 71 2-MeC (=NOMe) - 4-Me-thien-3 - yl CI£2 OEt 72 73 74 76 77 78 79 81 82 83 84 86 87 88 2-MeC (=NOMe) - 4-Me-thien-3-yl 2-MeC (OEt) 2-4-Me-thien-3-yl 2-COOMe-4 - Ne-thien-3 - yl IL 2-Et-4,5.diMe-thien-3-yl t! I1 2,4-diMe-5-Cl-thien-3 - yl vl vl t! 2,5-dißr-4-Me-thien-3-yl 2-Me-4-MeO-5-Br-thien-3-yl 2,4-diMe-5-COOMe-thien-3-yl 2,4-diMe-furan-3-yl 5-COOEt-N, 2,4-tri-Mepyrrol-3-yl Pyrazolyl1-CH2 CH2OEt cri2-c=--cn CI-I2OEt CH (ME) COOEt CH2OEt CH2COOC3H7i Pyrazolyl-l-CH2 CH2OEt CH2OCH2CH2OCH3 Tetrahydrofuryl-2-CH2 Pyrazolyl-l-CH2 CH20 t PyrazolylI-CH2 CH2OEt CH2OEt Pyrazolyl-l-CH2 Rf = 0,23 (hexane/ethyl acetate 4: 1) Smp. 76-78° Smp. 57-59° Smp. 68-70° Rf = 0,4 (I-Iexan/Ethylacetat 4: 1) Sdp. 142-44°/0,26 mbar of Smp. 49-50° Smp. 53-54° Rf = 0,47 (Diethyläther/hexane 7: 3) Rf-- 0.47 (Diethyläther/hexane 7: 3) Smp: 63-65° nD20 = 1,5242 nD23 = 1,5328 stop. 90-92° Smp. 24° Sdp. 168-170°/0,065 mbar of Smp. 78-80° Smp. 44-46° Sdp. 180°/0,0013 mbar of Sdp. 135°/0,0013 mbar of Sdp. 148-150°/0,0013 mbar of Smp. 100° stop. 37-38° syn: Smp. 89-91° anti: Smp. 75-760 syn: Smp. 123° Smp. 46-47° Smp. 119-21° Smp. 20-22° Sdp. 135°/9,0065 mbar of nD20 = 1,5273 nD20 -- 1,5112 nD20 = 1,5509 nD20 -- 1,5412 nD21 - 1,5321 Rf = 0,35 (cyclohexane/Ethylaeetat 7: 3) Smp. 68-73° Srnp. 75-77° Srnp. 98-99° Sdp. 140°/0,0065 mbar of Rf = 0,5 (Diethyläther) nD24 = 1,5422 No. 391,791 TABLE A (continuation) connection aryl Y Charaktedsierung No.
89 3,5-diMe-isoxazol-4-yl CH (ME) COOEt Smp. 49-50° 90 “CH2 OEt Smp. 45-46° 91 3,5-diEt-isoxazol-4-yl CH2 - C=-CH Sdp. 118°/0,0013 mbar of 92” CH2 - OEt Sdp. 107-108°/0,0013 mbar of nD20 = 1,4908 93 3,5-diMe-isothiazol-4-yl CH2 OEt Smp. 43-45° 94 “CH2 CH2 OMe 95” Pymzolyl-l-CH2 stop. 109-14° 96 “CH2C-=-CH stop. 109-12° 97 3-Me-5-EtO-pyrazol-4-yl CH2 CH2 OMe Smp. 111-113° 98 1,3,5-triMe-pyrazol-4-yl CH2 OEt Sdp. 130°/0,0013 mbar of 99 1,3,5-time-pyrazol-4-yl CH2CH2 OMe stop. 66-67° 100” CH2 - OC3 HTn Sdp. 135°/0,0013 mbar of 101 “CH2 - C=--CH Smp. 115-117° 102” pyrazolyl-l-CH2 Smp. 96-97° 103 1-Me-3,5-diEt-Pyrazol-4-yl CH2-OC3 HTn nD20 = 1,5008 104 “CH2 CH2 OMe Sdp. 130°/0,0013 mbar of 105,1.3 - diMe-5-EtO-pyrazol-4-yl CH2 OEt Smp. 54-56° of TEST RESULTS example 1: Herbicides effect after pre ¢m A_op_ likation pots (7 cm diameters) are filled with a mixture from peat substrate and sand. The upper surface of the mixture becomes with a means according to invention (e.g. in form of the Emulsionskonzentmtes in accordance with example B), and on that seed of Lepidium sprays sativum, Agrostis alba, Avena salva and Lolium perenne in each pot sown, according to which the seeds are covered by arena sativa and Lolium perenne with a thin (0,5 cm) layer TorfsubstIat sand mixture. The pots are let stand 21 days at ambient temperature with 14 to 17 hours daylight/day.
The determination the herbicides of the effect takes place at expiration of the 21-Tage-Periode. It covers a visual Absehätzung of the degree and the kind of the damage with the different plants.
The means according to invention are appliziert in above way in quantities according to 1.4 to 5.6 kg active substance/hectare. Herbicides effect, i.e. significant damage is observed, with the test plants.
Example 2: Herbicides effect after post office cm Applika! ion one proceeds similar to the procedure in accordance with example 1, whereby the means according to invention are appliziert with 2 to 4-Blatt-Stadium. (By graduated sowing the test plants reach at the same time 2-4 sheet stages).
Erfindungsgemäl] the EN means are appliziert again in quantities according to 1.4 kg/ha to 5.6 kg/Wirkstoff/ha. The visual determination the herbicides of the effect takes place 21 days after application of the attempt substance. It is observed herbicides effect.
Example; A selection of the means according to invention is more near examined in the following Vor'auflauf attempt.
Containers of 30 x 40 cm are gef'tült up to a depth by 6 cm with a mixture from Torfsubstmt and sand. The upper surface of the mixture becomes with a test liquid, the one connection of the general formula (I), e.g. in form of the emulsion concentrate in accordance with example B) in a certain concentration contains, sprayed. The spraying volume corresponds to 600 1 aqueous Testflüssigkeit/ha. The procedure is repeated with No. 391,791 different concentrations, whereby the concentrations become so more aware of that the desired application quantities are reached. Six Pfianzenarten become per Behalter ge.sau the number of seeds, which is gest by each Pflamenart, divert of the Keimpotendal of the seeds and of the initial growth rate of the individual plants. After Sliea of the seeds the treated flat one is covered also “thin layer (about 0,5 cm) of a Torfstubstrat/sand Gemiscbes.
The Behalter is then let stand 28 days at a temperature from 20 to 24 °C and tllglich to 14 to 17 hours with daylight (possibly artificial).
The determination the herbicides of the effect of the examined connection according to invention takes place right after completion of the 28 day period. The regulation covers a visual Abschiilzung of the degree and the kind of the damage of the different plants. Particularly favourable herbicides an effect with the connections No. 19, 20, 33, 34, 41, 54, 61 and 63 of the table A one observes among other things. Some the results with Applikaüonsmengen of 1 kg, obtained with these connections, Wkkstoff/ha are summarized in the following table B.
130 - 3938 TABLE B Pre era treatment I kg/ha connection Nr,/% damage 19 20 33 34 41 54 61 63 Amarant. purely? IL. 90 90 I00 I00 I00 I00 80 90 Capsella b.p. 80 I00 I00 80 90 70 70 90 Chenop. alb. 80 80 90 50 20 50 60 Galium aparine 80 10 50 0 10 10 50 Senecio vulg. 90 80 80 80 80 100 90 100 Stellsria media 90 70 70 80 50 50 70 90 Alfalfa 80 60 60 50 80 10 70 90 vl beans 0 0 20 20 0 0 1O I0 carrots 80 90 90 90 70 I00 80 90 cotton 20 0 10 0 0 0 20 0 flax 80 30 60 50 30 0 20 potatoes 0 10 I0 0 0 0 0 0 Sqja 50 10 30 30 0 10 30 Zuckmrüben 60 10 I 0 0 0 0 20 sunflowers I0 0 20 0 0 0 20 IO rape 0 10 30 50 0 0 0 Agropyron repens 90,100 90 60 80 90 90 A stis alba 100 I00 100 I00 100 I00 I00 100 Alopec. myos. 90 90 80 20 50 80 80 90 Apem frame venfi 100 I00 100,100,100,100,100,100 arena fama 80 80 80 40 80 90 50 90 Echinochloa C. flat steel bar. 90,100 90 90 90 100 90 90 corn 20 30 50 30 0 50 90 blowing 70 I00 90 90 0 I00 60 Beimiel 4: post office em treatment a further examination of a selection of exfindungsgemaßen means takes place in an Nachauflauf attempt, which is hgefllla't similarly to 6 Vorauflanfversuch DM described in example, with the difference that the Testfltlssigkeit is only appliziert in the 2bis 4-Blatt-Stadium. For this purpose the different plant types temporally graduated gest. the greenhouse conditions (temperature, Lich0 as in example 3. the herbicides effect likewise 28 days are according to application are determined and effected in the procedure in accordance with example 1.
Particularly favourable herbicides characteristics are observed among other things with the connections No. 19, 20, 33, 34, 41, 54, 61 and 63 of the table A. Some the results, which are obtained with the application quantity of 5 kg of Widramff/ha, are summarized in the table C.
No. 391,791 TABLE C treated plant post office em treatment 5 kg ha of connection No.] % damage 19 20 33 34 41 " 54 61 63* Amaran. retrofl. 90 80 70 50 80 60 80 90 CaposeUa b.p. 80 60 20 20 80 50 80 Chenop. alb. 90 40 40 20 20 40 30 Galium aparine 80 60 40 30 80 20 70 Senecio vulg. 80 50 70 80 90 90 80 90 Stellaria media 90 50 60 10 30 40 60 Alfalfa 80 60 20 10 50 20 70 beans 100 20 30 20 20 30 30 carrots 70 90 30 100 80 100,100 cotton 70 60 50 40 50 60 70 flax 80 70 90 100 80 90 40 potatoes 70 30 20 10 10 10 40 soy 90 30 30 30 20 30 30 Zuckerrü'ben 30 20 70 0 10 10 0 rape 40 20 10 10 30 60 50 sunflowers 60 50 30 80 40 60 90 Agropyron repens 70 30 70 50 50 50 30 Agrostis alba _ _ _ Alopec. myos. 80 90 80 70 60 90 80 90 Apera frame venfi 90,100,100,100,100,100 90 90 Avena fatua 90,100 90 80 90 100,100,100 Echinochloa C.G. 1) 80 60 80 80 90 70 80 90 2) 90 80 80 90 100 80 90 100 corn 80 60 100 90 30 30 70 wheat 70 90 80 50 10 60 60 rice 2) 40 30 10 50 30 30 30 * 4 kg/ha 1) “upland” conditions; 2) “paddy” conditions field test connection No. 19 Multikultur Feldscreening Versueh becomes in one pre em, under which the following conditions, weiteruntersueht:
Cultures:
Soy (“Steele”) - (so) cotton (“Stoneville 213”) (Cot) corn (LG 11) (CO) wheat (Svenno) (Wh) of weeds: Alopeeurus pratensis - (A1) Echinochloa crus galli - (Ech) Galium aparine t Chenopodium album and polyspermum Dieots Amaranthas retroflexus (all weeds, with which exception of Alopecurus pratensis, which was in-sown, were naturally occurring).
- Spraying volumes: 750 l/ha - number of attempts: 3 - Evaluation: 28 after day the Applikaüon.
- Standards: Alachlor (= o - Chlor-2',6' diethyl N methoxymethylacetanilid) and Metolaehlor [= a-Chlor-2' ethyl-6' methyl n (1-methyl-2-methoxyethyl) aeetanilid].
No. the 391,791 following of herbicides effect (% damage) was observed.
Connection kg/ha Cot CO Wh A1/Ech Dicots No. 19,0,6 0 0 10 63 92 43 1,25 3 3 53 80 100 67 2,5 5 7 80 92 100 87 Alachlor 1,25 0 0 0 l0 43 43 2,5 0 3 0 53 78 57 Metolaehlor of 1,25 0 0 0 33 100,2,5 0 0 0 73 100 43 above results in such a way show herbicides an effect those see in the trade standards present directly or superior is approximately monokotylen weeds, and which dikotylen this standards approximately weeds are superior.
The herbicides effect is selective in soy and cotton and with the deepest application quantity also in corn. The invention relates to compositions for controlling undesired plants which comprise, as active component, a compound of the general formula I. <IMAGE> 1. Means for the fight against unwanted plants, thereby characterized that they contain as an effective component a connection of the general formula COCH2CI acre-n, where acre one by one or more substituents of the row halogen, c1,4 alkyl, c1,4 Alkoxy, c1,4 AlkylS, CI_4 alkyl THEN, C2_4-Alkanoyl, C (=NOC1 _4Alkyl) - c1 _3alkyl, C (OC1 _4Alkyl) 2 - c1 _3 alkyl, and C1.5Alkoxy-carbonyl substituted heteroaromatisehe group of the row Thien-3-yl, Furan-3-yl, Pyrrol-3-yl, Isoxazol-4-yl, Isothiazol-4-yl and Pyrazol-4-yl means, and, stands for Y for a hydrocarbon selected from the row C3_8-Alkenyl and C3_8Alkinyl, unsubstituiert or by halogen, selected from the row F, CI or Br, is substituted; or for by F, CI or Br substituted c1 _8Alkyl stands; or a group of CHR1 - COY1 means, in which g 1 stands for H or c1 _5 alkyl, and Y1 Hydroxy, c1,5 Alkoxy, C3 _5 Alkinyloxy, c1 _4 Alkylamino, Di (c1,4 alkyl) amino or NH-N--C (C1_3) alkyl) 2 means, or a group of R2 - Az meant, in which R2 for unsubsdtuiertes or by c1,5 alkyl substimiertes CH2 or CH2 - CH2 stands, and selected 3,5-Dimethyl-l-pyrazolyl, 1,2,4-Triazolyl, 2-Pyrimidinyl means Az a heteroaromaüschen ring from 1-Pyrazolyl, or from one if necessary by or two substituents of the row C1.4Alkyl or c1 _4 Alkylthio substituted Furyl, Thienyl, Thiazolyl, Isoxazolyl, 1,3,4-Oxadiazolyl, 1; 2,4-Oxadlazolyl, 1,3,4-Thiadiazolyloder 1,3,4-Triazolylring, No. 391,791 or a group of A-OR3 mean, where R3 for H or meant for if necessary by Halogeu, CN, or c1 .4Alkoxy substituted c1 _8 alkyl, and A a unsubstituierten or by c1 _5 Alkoxy monosubstituted hydrocarbon remainder, which can be linked with R3, under formation of a 1,3-Dioxolanringes, whereby the Nund of O-atoms, which are connected by means of A, is through up to 3 carbon atoms from each other separated; or a Gmpl CHR5 - CHR5, =NOR4 means, where R4 c1 _4Alkyl and R5 and R5' mean independently H or CH3. 2. Means according to requirement 1, by characterized that it contains a connection, where acre stands for a 3-Thienylring that in o, o' of SteUung of the Chloracetamidgruppe at least is subsütuiert by substituents selected of the row consisting of halogen, Ci.4 AlkyI, C2,4 Alkanoyl, C (=NOCi_4 alkyl) - c1,3 alkyl' C (OC1-4AIkyl) 2 " c1 - 3 alkyl, C 1-4Alkyl'S, C 1-4Alkyl " SO, C1-4Alk°xy'carb°nyI, C 1-4Alk°xy, whereby a allfillliger additional substituent is ansgewähIt from the row c1 .4AlkyI, halogen and c1,4 Alkoxycarbonyl. 3. Means according to requirement 2, by characterized that it contains a connection, where acre 3-Thienyl 2,4-disubstituiert means,4 Alkoxy by substituents selected to the c1,4 alkyl and c1. 4. Means according to requirement 3, by characterized that it contains a connection, where acre and Y respectable.
for and/or.
and/or.
and/or.
and/or.
and/or.
and/or.
and/or.
a) 2,4-Dime, thyl thien: 3-yl and Pymzol l ylmethyl b) and 1 (Pyrazol1-yl) ethyl c)…. and CH2 OC2 H5 d)…. and CH2 OC3 H7n_ e)…. and CH (CH3) - CH=NOCH3 f) 2-Methyl-4-ethyl-thien-3-yl and CH2 OC2 H5 g) 2-Methyl-4-methoxy-thien-3 - yl and Pyrazol1-ylmethyl tl II h) and CH2CH2 OC2 H5 stand.
Means according to requirement 3, by characterized that it contains the connection, where acre for 2,4-Dimethyl-thien-3-yl and Y stand for CH2 OCH3 for CI-I (CH3). 6. Means according to requirement 3, by characterized that it contains the connection, where acre for 2,4-Dimethyl-thieu-3-yl and Y stand for 2-Methyl-l, 3,4-1H-triazol-5-yl.