Herbicide combination with acylated aminophenylsulfonylureas

Plant protecting and regulating compositions – Plant growth regulating compositions – Plural active ingredients

Reexamination Certificate

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C504S136000

Reexamination Certificate

active

06498126

ABSTRACT:

The invention is in the technical field of crop protection products which can be employed against harmful plants, for example in plant crops, and which comprise, as active ingredients, a combination of at least two herbicides.
The publication WO 95/29899 discloses acylated aminophenyl-sulfonylureas and their salts and also their use as herbicides and/or plant growth regulators. Compounds which are of particular interest amongst compounds of this class of structure are those of the formula (I) and their salts,
where
R
1
is hydrogen or (C
1
-C
4
)alkyl, preferably methyl or ethyl, in particular methyl,
R
2
is hydrogen or (C
1
-C
4
)alkyl, preferably methyl or ethyl, in particular methyl,
R
3
is hydrogen, (C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy, (C
2
-C
4
)alkenoxy, (C
2
-C
4
)alkynoxy, (C
3
-C
6
)cycloalkyl, each of the 5 last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, (C
1
-C
4
)alkoxy and (C
1
-C
4
)alkylsulfonyl,
 preferably hydrogen, methyl, trifluoromethyl, ethyl, n-propyl, isopropyl, cyclopropyl, methoxy or ethoxy, preferably hydrogen, methyl or methoxy, in particular hydrogen,
one of the radicals X and Y is halogen, (C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, each of the three last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C
1
-C
4
)alkoxy and (C
1
-C
4
)alkylthio,
and the other of the radicals X and Y is (C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy or (C
1
-C
4
)alkylthio, each of the three last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C
1
-C
4
)alkoxy and (C
1
-C
4
)-alkylthio,
 in particular X and Y are in each case methoxy, and
Z is CH or N, in particular CH.
The efficacy of these herbicides against harmful plants in the plant crops is at a high level, but depends in general on the application rate, the formulation in question, the harmful plants or spectrum of harmful plants to be controlled in each case, the climatic conditions, the soil conditions and the like. Another criterion is the duration of action, or the breakdown rate of the herbicide. If appropriate, changes in the sensitivity of harmful plants, which may occur upon prolonged use of the herbicides or within geographic limitations must also be taken into consideration. The compensation of losses in action in the case of individual harmful plants by increasing the application rates of the herbicides is only possible to a certain degree, for example because such a procedure frequently reduces the selectivity of the herbicides or because the action is not improved, even when applying higher rates. In some cases, the selctivity in crops can be improved by adding safeners. In general, however, there remains a need for methods to achieve the herbicidal action with a lower application rate of active ingredients. Not only does a lower application rate reduce the amount of an active ingredient required for application, but, as a rule, it also reduces the amount of formulation auxiliaries required. It both reduces the economic input and improves the ecological compatibility of the herbicide treatment.
One possibility of improving the application profile of a herbicide can consist in combining the active ingredient with one or more other active ingredients. However, the combined use of a plurality of active ingredients does not infrequently cause phenomena of physical and biological incompatibility, for example a lack of stability in a coformulation, decomposition of an active ingredient, or antagonism of the active ingredients. Desired, in contrast, are combinations of active ingredients with an advantageous activity profile, high stability and if possible a synergistically improved action, which allows reduction of the application rate in comparison with the individual application of the active ingredients to be combined.
Surprisingly, it has now been found that active ingredients from the group of the abovementioned herbicides of the formula (I) or their salts in combination with certain structurally different herbicides act together in a particularly advantageous manner for instance when they are employed in plant crops which are suitable for the selective use of the herbicides, if appropriate with addition of safeners.
The invention therefore relates to herbicide combinations with an effective content of components (A) and (B), where
(A) denotes one or more herbicides from the group of the compounds of the formula (I) or their salts,
 where
R
1
is hydroger or (C
1
-C
4
)alkyl, preferably methyl or particular methyl,
R
2
is hydrogen or (C
1
-C
4
)alkyl, preferably methyl or ethyl, in particular methyl,
R
3
is hydrogen, (C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy, (C
2
-C
4
)alkenoxy, (C
2
-C
4
)alkynoxy, (C
3
-C
6
)cycloalkyl, each of the 5 last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, (C
1
-C
4
)alkoxy and (C
1
-C
4
)alkylsulfonyl,
 preferably hydrogen, methyl, trifluoromethyl, ethyl, n-propyl, isopropyl, cyclopropyl, methoxy or ethoxy, preferably hydrogen, methyl or methoxy, in particular hydrogen,
one of the radicals X and Y is halogen, (C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, each of the three last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C
1
-C
4
)alkoxy and (C
1
-C
4
)alkylthio,
and the other of the radicals X and Y is (C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy or (C
1
-C
4
)alkylthio, each of the three last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C
1
-C
4
)alkoxy and (C
1
-C
4
)alkylthio,
 in particular X and Y are in each case methoxy, and
Z is CH or N, in particular CH and
(B) denotes one or more herbicides from the group of the compounds consisting of (given is the common name and the reference in “The Pesticide Manual” 11th Ed., British Crop Protection Council 1997, in short “PM”)
(B1) herbicides which act selectively in some dicotyledonous crops against monocotyledonous and dicotyledonous harmful plants, selected from the group consisting of:
(B1.1) ethofumesate (PM, pp. 484-486), i.e. (2-ethoxy-2,3 dihydro-3,3-dimethylbenzofuran-5-yl) methanesulfonate, (application rate: 10-3000 g AS/ha, preferably 20-1500 g AS/ha; quantitative ratio A:B=1:1000-12:1, preferably 1:300-4:1);
(B1.2) chloridazon (PM, pp. 215-216), i.e. 5-amino-4-chloro-2-phenylpyridazin-3(2H)-one, (application rate: 50-3000 g AS/ha, preferably 80-2000 g AS/ha; quantitative ratio A:B=1:3000-1:1, preferably 1:700-1:3);
(B1.3) triflusulfuron and its esters, such as the methyl ester, (PM, pp. 1250-1252), i.e. 2-[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]-carbamoyl-sulfamoyl]-6-methylbenzoic acid and its methyl ester, (application rate: 1-50 g AS/ha, preferably 2-40 g AS/ha; quantitative ratio A:B=1:50-1:2, preferably 1:15-1:3);
(B1.4) metamitron (PM, pp. 799-801), i.e. 4-amino-4,5-dihydro-3-methyl-6-phenyl-1,2,4-triazin-5-one, (application rate: 50-5000 g AS/ha, prehferably 80-4000 g AS/ha; quantitative ratio A:B=1:5000-1:1, preferably 1:1300-1:2)
(B1.5) metazachlor (PM, pp. 801-803), i.e. 2-chloro-N-(2,6-dimethylphenyl)-N-(1H-pyrazol-1-ylmethyl)-acetanilide, (application rate: 100-3000 g AS/ha, preferably 200-2500 g AS/ha; quantitative ratio A:B=1:3000-2:1, preferably 1:800-1:1);
(B1.6) napropamide (PM, pp. 866-868), i.e. (R,S)-N,N-diethyl-2-(1-naphthyloxy)propanamide, (application rate: 200-3000 g AS/ha, preferably 300-2500 g AS/ha; quantitative ratio A:B=1:3000-4:1, preferably 1:800-2:1);
(B1.7) carbetamide (PM, pp. 184-185), i.e. (R)-1-(ethylcarbamoyl)ethyl carbanilate, (application rate: 500-5000 g AS/ha, preferably 800-4000 g AS/ha; quantitative ratio A:B=1:5000-10:1, preferably 1:1300-5:1);
(B1.8) dimef

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