Claims
- 1. A herbicidal composition comprising
- a) at least one cyclohexenone oxime ether of the formula I ##STR4## where the variables have the following meanings: R.sup.a is ethyl or n-propyl;
- R.sup.b, R.sup.d and R.sup.e are each hydrogen;
- R.sup.c is tetrahydropyran-3-yl, tetrahydropyran-4-yl or tetrahydrothiopyran-3-yl;
- Alk is a chain --CH.sub.2 CH.sub.2 --O-- or --CH.sub.2 CH(CH.sub.3)--O--;
- R.sup.f is 4-fluorophenyl or 4-chlorophenyl, and
- b) at least one herbicidal compound selected from the groups b.sub.1) to b.sub.20)
- b.sub.1) the amines
- 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);
- b.sub.2) the anilides
- S-[2-[(4-chlorophenyl)(1-methylethyl)amino]-2-oxoethyl] O,O-dimethyl phosphorodithioate (common name: anilofos) and
- 2-(1,3-benzothiazol-2-yloxy)-N-methylacetanilide (common name: mefenacet);
- b.sub.3) 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);
- b.sub.4) 3-isopropyl-1H-2,1,3-benzothiadiazin-4-(3H)one 2,2-dioxide (common name: bentazone);
- b.sub.5) the bleachers
- 4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yltoluene-4-sulfonate (common name: pyrazolynate, pyrazolate) and
- 2-(2-chloro-4-mesylbenzoyl)cyclohexane-1,3-dione (common name: sulcotrione);
- b.sub.6) 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)thiocarbamate (common name: pyributicarb) and
- 4-chlorobenzyl N,N-diethylthiocarbamate (common name: thiobencarb, benthiocarb);
- b.sub.7) 3,7-dichloroquinoline-8-carboxylic acid (common name: quinchlorac);
- b.sub.8) the chloroacetanilides
- N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)acetamide (common name: butachlor),
- (Z)-N-but-2-enyloxymethyl-2-chloro-2',6'-diethylacetanilide (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);
- b.sub.9) the cyclohexenones
- 2-[1-(ethoxyimino)butyl]-3-hydroxy-5-(tetrahydrothiopyran-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);
- b.sub.10) N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitrobenzenamine (common name: pendimethalin);
- b.sub.11) 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);
- b.sub.12) the protoporphyrinogen IX oxidase inhibitors
- 2-[4-(2,4-dichloro-m-toluyl)-1,3-dimethylpyrazol-5-yloxy]-4'-methylacetophenone (common name: benzofenap) and
- 2-[4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yloxy]acetophenone (common name: pyrazoxyfen);
- b.sub.13) 3,5-bis(methylthiocarbonyl)-2-difluoromethyl-4-(2-methylpropyl)-6-trifluoromethylpyridine (common name: dithiopyr);
- b.sub.14) 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;
- b.sub.15) 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-ylcarbamoylsulfamoyl)-O-toluate (common name: bensulfuron-methyl),
- 1-(4,6-dimethoxy-1,3,5-triazin-2-yl)-3-[2-(2-methoxyethoxy)phenylsulfonyl]urea (common name: cinosulfuron),
- 1-{[2-(cyclopropylcarbonyl)phenyl]aminosulfonyl}-3-(4,6-dimethoxypyridin-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: imazosulfuron) and ethyl 5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate (common name: pyrazosulfuron-ethyl);
- b.sub.16) the triazines
- N.sup.2 -(1,2-dimethylpropyl)-N.sup.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);
- b.sub.17) 2,3-dihydro-3,3-dimethyl-5-benzofuranyl ethanesulfonate (common name: benfuresate);
- b.sub.18) 1-diethylcarbamoyl-3-(2,4,6-trimethylphenylsulfonyl)-1,2,4-triazole (common name: cafenstrole);
- b.sub.19) (1RS,2SR,4SR)-1,4-epoxy-p-menth-2-yl 2-methylbenzyl ether (common name: cinmethylin), and
- b.sub.20) S-2-methylpiperidinocarbonylmethyl O,O-dipropyl phosphorodithioate (common name: piperophos),
- in a synergistically effective amount where the cyclohexenone oxime ether and the herbicide from group b) in the weight ratio of from 1:0.1 to 1:40.
- 2. The synergistic herbicidal composition defined in claim 1, comprising at least one of the following 33 herbicides:
- b.sub.1) 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);
- b.sub.2) 2-(1,3-benzothiazol-2-yloxy)-N-methylacetanilide (common name: mefenacet);
- b.sub.3) (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);
- b.sub.4) 3-isopropyl-1H-2,1,3-benzothiadiazin-4-(3H)one 2,2-dioxide (common name: bentazone);
- b.sub.5) 4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yltoluene-4-sulfonate (common name: pyrazolynate, pyrazolate) and 2-(2-chloro-4-mesylbenzoyl)cyclohexane-1,3-dione (common name: sulcotrione);
- b.sub.6) S-benzyl 1,2-dimethylpropyl(ethyl)thiocarbamate (common name: esprocarb),
- N-(ethylthiocarbonyl)azepane (common name: molinate) and
- 4-chlorobenzyl N,N-diethylthiocarbamate (common name: thiobencarb);
- b.sub.7) 3,7-dichloroquinoline-8-carboxylic acid (common name: quinchlorac);
- b.sub.8) N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)acetamide (common name: butachlor),
- (Z)-N-but-2-enyloxymethyl-2-chloro-2',6'-diethylacetanilide (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);
- b.sub.11) ethyl 2-[4-(6-chlorobenzoxazol-2-yloxy)phenoxy]propionate (common name: fenoxaprop-ethyl);
- b.sub.12) 2-[4-(2,4-dichloro-m-toluyl)-1,3-dimethylpyrazol-5-yloxy]-4'-methylacetophenone (common name: benzofenap) and 2-[4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yloxy]acetophenone (common name: pyrazoxyfen);
- b.sub.13) 3,5-bis(methylthiocarbonyl)-2-difluoromethyl-4-(2-methylpropyl)-6-trifluoromethylpyridine (common name: dithiopyr);
- b.sub.15) 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-ylcarbamoylsulfamoyl)-O-toluate (common name: bensulfuron-methyl),
- 1-(4,6-dimethoxy-1,3,5-triazin-2-yl)-3-[2-(2-methoxyethoxy)phenylsulfonyl]urea (common name: cinosulfuron),
- 1-{[2-(cyclopropylcarbonyl)phenyl]aminosulfonyl}-3-(4,6-dimethoxypyridin-2-yl)urea (common name: cyclosulfamuron),
- N-(2-chloroimidazol[1,2-a]pyridin-3-ylsulfonyl)-N'-(4,6-dimethoxy-2-pyrimidyl)urea (common name: imazosulfuron) and
- ethyl 5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate (common name: pyrazosulfuroneethyl);
- b.sub.16) N.sup.2 -(1,2-dimethylpropyl)-N.sup.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);
- b.sub.19) (1RS,2SR,4SR)-1,4-epoxy-p-menth-2-yl 2-methylbenzyl ether (common name: cinmethylin), and
- b.sub.20) S-2-methylpiperidinocarbonylmethyl O,O-dipropyl phosphorodithioate (common name: piperophos).
- 3. The synergistic herbicidal composition defined in claim 1, further comprising at least one liquid or solid carrier, and optionally at least one surface-active substance.
- 4. The synergistic herbicidal composition defined in claim 1, comprising the cyclohexenone oxime ether and the herbicide from group b) in the weight ratio of from 1:0.2 to 1:30.
- 5. The synergistic herbicidal composition defined in claim 3, comprising the cyclohexenone oxime ether and the herbicide from group b) in the weight ratio of from 1:0.1 to 1:40.
- 6. The synergistic herbicidal composition defined in claim 3, comprising the cyclohexenone oxime ether and the herbicide from group b) in the weight ratio of from 1:0.2 to 1:30.
- 7. A process for preparing the synergistic herbicidally active composition defined in claim 1, which comprises mixing
- a) a herbicidally active amount of at least one cyclohexenone oxime ether of the formula I and
- b) a synergistically active amount of at least one herbicidal compound from group b),
- with at least one inert liquid or and solid carrier and optionally at least one surface-active substance.
- 8. A method of controlling undesired vegetation, which comprises treating the vegetation with
- a) a herbicidally active amount of at least one cyclohexenone oxime ether of the formula I as defined in claim 1 and
- b) a synergistically active amount of at least one herbicidal compound from group b) as defined in claim 1,
- simultaneously or in succession before or during the emergence of the undesired plants.
- 9. A method of selectively controlling undesired vegetation, which comprises treating the leaves of the crop plants and of the undesired plants post-emergence with
- a) a herbicidally active amount of at least one cyclohexenone oxime ether of the formula I as defined in claim 1 and
- b) a synergistically active amount of at least one herbicidal compound from group b) as defined in claim 1.
- 10. The method of claim 9, wherein the crop plant is rice, wheat, corn, barley or millet.
Priority Claims (1)
Number |
Date |
Country |
Kind |
195 34 848 |
Sep 1995 |
DEX |
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Parent Case Info
This Application is a 371 of PCT/EP96/04000.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/EP96/04000 |
9/12/1996 |
|
|
3/17/1998 |
3/17/1998 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO97/10710 |
3/27/1997 |
|
|
US Referenced Citations (15)
Foreign Referenced Citations (1)
Number |
Date |
Country |
9304581 |
Mar 1993 |
WOX |
Non-Patent Literature Citations (1)
Entry |
The Agrochemial Handbook, 3r ED., The Royal Society of Chemistry. |