Patent EA-000869-B1 (EA)
Title: Synergistic herbicidal mixtures containing cyclohexenoneoxime ether
Inventor: SIEVERNICH BERND
IPC: A01N43/18
Filed: 1996-09-12
Abstract: 1. A herbicidal mixture, containing  a) at least one cyclohexenoneoxime ether of the formula I   where the variables have the following meanings: R<a> is ethyl or n-propyl; R<b>, R<d> and R<e> are each hydrogen; R<c> is tetrahydropyran-3-yl, tetrahydropyran-4-yl or tetrahydrothiopyran-3-yl; Alk is a chain -CH2CH2-O- or -CH2CH(CH3)-O-; R<f> is 4-fluorophenyl or 4-chlorophenyl, and b) at least one of the following 44 herbicidal compounds from the groups b1) to b20) b1) the amides  2-bromo-3,3-dimethyl-N-(1-methyl-1-phenylethyl)-butyramide (common name bromobutide), S-(1-methyl-1-phenylethyl) 1-piperidinecarbothioate (common name dimepiperate), 4-ethoxybenz-2',3'-dihydrochloroanilide (common name: etobenzanid) and N-(3,4-dichlorophenyl)propanamide (common name propanil); b2) the anilides S-[2-[(4-chlorophenyl)(1-methylethyl)amino]-2-oxo-ethyl] O,O-dimethylphosphorodithioate (common name anilofos) and 2-(1,3-benzothiazol-2-yloxy)-N-methylacetanilide (common name mefenacet); b3) the aryloxyalkanecarboxylic acids (2,4-dichlorophenoxy)acetic acid (common name 2,4-D), 4-(4-chloro-2-methylphenoxy)butanecarboxylic acid (common name MCPB) and 2-(2-naphthyloxy)propionanilide (common name naproanilide); b4) 3-isopropyl-1H-2,1,3-benzothiadiazin-4-(3H)one 2,2-dioxide (common name: bentazone); b5) the bleachers (disinfectant) 4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yl-toluene-4-sulfonate (common name pyrazolynate, pyrazolate) and 2-(2-chloro-4-mesylbenzoyl)-cyclohexane-1,3-dione (common name sulcotrione); b6) the carbamates S-benzyl 1,2-dimethylpropyl(ethyl)thiocarbamate (common name esprocarb), N-(ethylthiocarbonyl)azepane (common name molinate), O-3-tert-butylphenyl 6-methoxy-2-pyridyl(methyl)thio-carbamate (common name pyributicarb) and 4-chlorobenzyl N,N-diethylthiocarbamate (common name thiobencarb, benthiocarb); b7) 3,7-dichloroquinoline-8-carboxylic acid (common name quinclorac); b8) the chloroacetanilides  N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)-acetamide (common name butachlor), (Z)-N-but-2-enyloxymethyl-2-chloro-2',6'-diethyl-acetanilide (common name butenachlor), N-(2-propoxyethyl)-2-chloro-N-(2,6-diethylphenyl)-acetamide (common name pretilachlor) and .alpha.-chloro-N-(3-methoxy-2-thienyl)methyl-2',6'-dimethylacetanilide (common name thenylchlor); b9) the cyclohexenones 2-[1-(ethoxyimino)butyl]-3-hydroxy-5-(tetrahydrothio-pyran-3-yl)-2-cyclohexen-1-one (common name cycloxydim) and (E/Z)-2-[1-(ethoxyimino)butyl]-5-[2-(ethylthio)-propyl]-3-hydroxycyclohex-2-enone (common name sethoxydim); b10) N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitrobenzen-amine (common name pendimethalin); b11) the phenoxyphenoxypropionic acid esters  n-butyl (R)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy] propionate (common name cyhalofop-butyl) and ethyl 2-[4-(6-chlorobenzoxazol-2-yloxy)phenoxy]-propionate (common name fenoxaprop-ethyl); b12) the protoporphyrinogen IX oxidase inhibitors  2-[4-(2,4-dichloro-m-toluyl)-1,3-dimethyl-pyrazol-5-yloxy]-4'-methylacetophenone (common name benzofenap) and 2-[4-(2,4-dichlorobenzoyl)-1,3-dimethylpyra-zol-5-yloxy]acetophenone (common name pyrazoxyfen); b13) 3,5-bis(methylthiocarbonyl)-2-difluoromethyl-4-(2-methylpropyl)-6-trifluoromethylpyridine (common name dithiopyr); b14) the pyrimidyl ethers  sodium 2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]-benzoate and methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-[1-(methoxyimino)ethyl]benzoate; b15) the sulfonylureas 1-(4,6-dimethoxypyrimidin-2-yl)-3-[1-methyl-4-(2-methyl-2H-tetrazol-5-yl)pyrazol-5-ylsulfonyl]urea  (common name azimsulfuron), methyl .alpha.-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfa-moyl)-O-toluate (common name bensulfuron-methyl), 1-(4,6-dimethoxy-1,3,5-triazin-2-yl)-3-[2-(2-meth-oxyethoxy)phenylsulfonyl]urea (common name cinosulfuron), 1-{[2-(cyclopropylcarbonyl)phenyl] aminosulfonyl}-3-(4,6-dimethoxypyrimidin-2-yl)urea (common name cyclosulfamuron), [[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-2-ethoxyphenyl sulfamic acid ester (Common name ethoxysulfuron), N-(2-chloroimidazo[1,2-a]pyridin-3-ylsulfonyl)-N'-(4,6-dimethoxy-2-pyrimidyl)urea (common name imazo-sulfuron) and ethyl 5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfa-moyl)-1-methylpyrazole-4-carboxylate (common name pyrazosulfuron-ethyl); b16) the triazines  N<2>-(1,2-dimethylpropyl)-N<4>-ethyl-6-methylthio-1,3,5-triazine-2,4-diamine (common name dimethametryn) and bis(ethylamino)-6-methylthio-1,3,5-triazine (common name: simetryn, simetryne); b17)2,3-dihydro-3,3-dimethyl-5-benzofuranyl ethane-sulfonate (common name benfuresate); b18) 1-diethylcarbamoyl-3-(2,4,6-trimethylphenylsulfonyl)-1,2,4-triazole (common name cafenstrole); b19) (1RS,2SR,4SR)-1,4-epoxy-p-menth-2-yl 2-methylbenzyl ether (common name cinmethylin), and b20) S-2-methylpiperidinocarbonylmethyl O,O-dipropyl phosphorodithioate (common name piperophos). 2. A herbicidal mixture as claimed in claim 1, containing as component b) at least one of the following 33 herbicides: b1) 2-bromo-3,3-dimethyl-N-(1-methyl-1-phenylethyl)-butyramide (common name bromobutide), S-(1-methyl-1-phenylethyl) 1-piperidinecarbothioate (common name dimepiperate), 4-ethoxybenz-2',3'-dihydrochloroanilide (common name etobenzanid) and N-(3,4-dichlorophenyl)propanamide (common name propanil); b2) 2-(1,3-benzothiazol-2-yloxy)-N-methylacetanilide, (common name mefenacet); b3) (2,4-dichlorophenoxy)acetic acid (common name 2,4-D), 4-(4-chloro-2-methylphenoxy)butanecarboxylic acid (common name MCPB) and 2-(2-naphthyloxy)propionanilide (common name naproanilide); b4) 3-isopropyl-1H-2,1,3-benzothiadiazin-4-(3H)one 2,2-dioxide (common name bentazone); b5) 4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yl-toluene-4-sulfonate (common name; pyrazolynate, pyrazolate) and 2-(2-chloro-4-mesylbenzoyl)-cyclohexane-1,3-dione (common name sulcotrione); b6) S-benzyl 1,2-dimethylpropyl(ethyl)thiocarbamate (common name esprocarb), N-(ethylthiocarbonyl)azepane (common name molinate), 4-chlorobenzyl N,N-diethylthiocarbamate (common name thiobencarb); b7) 3,7-dichloroquinoline-8-carboxylic acid (common name quinclorac); b8) N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)-acetamide (common name butachlor), (Z)-N-but-2-enyloxymethyl-2-chloro-2',6'-diethyl-acetanilide (common name: butenachlor), N-(2-propoxyethyl)-2-chloro-N-(2,6-diethylphenyl)-acetamide (common name pretilachlor) and .alpha.-chloro-N-(3-methoxy-2-thienyl)methyl-2',6'-dimethylacetanilide (common name thenylchlor); b11) ethyl 2-[4-(6-chlorobenzoxazol-2-yloxy)phenoxyl-propionate (common name fenoxaprop-ethyl); b12) 2-[4-(2,4-dichloro-m-toluyl)-1,3-dimethyl-pyrazol-5-yloxy]-4'-methylacetophenone (common name benzofenap) and 2-[4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol- 5-yloxy]acetophenone (common name pyrazoxyfen); b13) 3,5-bis(methylthiocarbonyl)-2-difluoromethyl-4-(2-methylpropyl)-6-trifluoromethylpyridine (common name dithiopyr); b15) 1-(4,6-dimethoxypyrimidin-2-yl)-3-[1-methyl-4-(2-methyl-2H-tetrazol-5-yl)pyrazol-5-ylsulfonyl]urea  (common name azimsulfuron), methyl .alpha.-(4,6-dimethoxypyrimidin-2-ylcarbamoylsul-famoyl)-O-toluate (common name bensulfuron-methyl), 1-(4,6-dimethoxy-1,3,5-triazin-2-yl)-3-[2-(2-meth-oxyethoxy)phenylsulfonyl]urea (common name cino-sulfuron), 1-{[2-(cyclopropylcarbonyl)phenyl]aminosulfonyl}-3-(4,6-dimethoxypyrimidin-2-yl)urea (common name cyclosulfamuron), N-(2-chloroimidazo[1,2-alpyridin-3-ylsulfonyl)-N'-(4 , 6 - dimethoxy-2-pyrimidyl)urea (common name imazosulfuron) and ethyl 5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfa-moyl)-1-methylpyrazole-4-carboxylate (common name pyrazosulfuron-ethyl); b16) N<2>-(1, 2-dimethylpropyl)-N<4>-ethyl-6-methylthio-1,3,5-triazine-2,4-diamine (common name: dimethametryn) and bis(ethylamino)-6-methylthio-1,3,5-triazine (common name simetryn , simetryne); b19) (1RS, 2SR, 4SR)-1,4-epoxy-p-menth-2-yl 2-methylbenzyl ether (common name cinmethylin), and b20) S-2-methylpiperidinocarbonylmethyl O,O-dipropyl phosphorodithioate (common name piperophos). 3. A herbicidal composition containing at least one liquid and/ or solid carrier, if desired at least one surface-active substance, and a) a herbicidally active amount of at least one cyclohexenoneoxime ether of the formula I as claimed in claim 1 and  b) a synergistically active amount of at least one herbicidal compound from group b) as claimed in claim 1 or 2. 4. A herbicidal mixture as claimed in claim 1 or 2, containing at least one cyclohexenoneoxime ether of the formula I and at least one herbicide from group b) in the weight ratio from 1:0.1 to 1:40. 5. A herbicidal mixture as claimed in claim 1 or 2, containing at least one cyclohexenoneoxime ether of the formula I and at least one herbicide from group b) in the weight ratio from 1:0.2 to 1:30. 6. A herbicidal mixture as claimed in claim 3, containing at least one cyclohexenoneoxime ether of the formula I and at least one herbicide from group b) in the weight ratio from 1:0.1 to 1:40. 7. A herbicidal mixture as claimed in claim 3, containing at least one cyclohexenone oxime ether of the formula I and at least one herbicide from group b) in the weight ratio from 1:0.2 to 1:30. 8. A process for preparing herbicidally active compositions, which comprises mixing a) a herbicidally active amount of at least one cyclohexenoneoxime ether of the formula I as claimed in claim 1 and b) a synergistically active amount of at least one herbicidal compound from group b) as claimed in claim 1 or 2 with at least one inert liquid and/or solid carrier and, if desired, with at least one surface-active substance. 9. A method of controlling undesired vegetation, which comprises applying a) a herbicidally active amount of at least one cyclohexenoneoxime ether of the formula I as claimed in claim 1 and b) a synergistically active amount of at least one herbicidal compound from group b) as claimed in claim 1 or 2 simultaneously or in succession before or during the emergence of the undesired plants. 10. A method of selectively controlling undesired vegetation, which compr