Herbicidal compositions with acylated aminophenylsulfonylureas

Details Herbicidal compositions with acylated aminophenylsulfonylureas Herbicidal compositions with acylated aminophenylsulfonylureas

1999-08-10

2002-11-26

Pryor, Alton (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C504S128000, C504S134000, C504S136000

Reexamination Certificate

active

06486096

ABSTRACT:

The invention is in the field of the crop protection products which can be employed against harmful plants in plant crops and which comprise, as herbicidally active substances, a combination of two or more herbicides.
The publication WO 95/M29899 discloses acylated aminophenylsulfonylureas and their salts, and their use as herbicides and/or plant growth regulators. Compounds of this structural class which are of particular interest are the compounds of the formula (I) and their salts
in which
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 H, (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 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, where each of the three last-mentioned radicals is unsubstituted or substituted by one or more radicals 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, where each of the three last-mentioned radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C
1
-C
4
)alkoxy and (C
1
-C
4
)alkylthio, in particular X and Y are each methoxy, and
Z is CH or N, in particular CH.
The efficacy of these herbicides against harmful plants in the plant crops is high, but generally depends on the application rate, the preparation in question, the harmful plants to be controlled or the harmful plant spectrum, the climatic conditions, the soil conditions etc. Another criterion is the duration of action, or the degradation rate of the herbicide. If appropriate, changes in the sensitivity of harmful plants, which may occur upon prolonged use of the herbicides or within a geographically limited area, must also be taken into consideration. The loss of action against individual plants can only be compensated for to some extent by higher application rates of the herbicides e.g. because the selectivity of the herbicides is thereby frequently adversely affected or improved efficacy is not achieved even at relatively high application rates. Sometimes, the selectivity in crops can be improved by the addition of safeners. In general, however, there is always a demand for methods to achieve the herbicidal effect with lower application rates of active substances. A lower application rate not only reduces the amount of an active substance required for application, but as a rule also reduces the amount of formulation auxiliaries required. Both reduce the economic outlay and improve the eco-friendliness of the herbicide treatment.
One possibility for improving the use profile of a herbicide may consist in combining the active substance with one or more other active substances which contribute the desired additional properties. However, the combined use of a plurality of active substances does not infrequently lead to phenomena of a physical and biological incompatibility, for example lacking stability of a coformulation, decomposition of an active substance or antagonism of the active substances. In contrast, what is desired are combinations of active substances with a favorable profile of action, high stability and as synergistic an increased action as possible, which allows the application rate to be reduced in comparison with the individual application of the active substances to be combined.
Surprisingly, it has now been found that active substances from the group of the abovementioned herbicides of the formula (I) or their salts in combination with specific structurally different herbicides interact especially favorably when they are employed in plant crops which are suitable for the selective use of the herbicides, if appropriate with the addition of safeners.
The invention therefore relates to herbicide combinations having an active content of components (A) and (B), wherein
(A) is one or more herbicides from the group of the abovementioned compounds of formula (I) or their salts, and
(B) is one or more herbicides from the group of the compounds which consists of
(B1) foliar- and soil-acting herbicides which are effective selectively in cereals and some dicotyledonous crops against monocotyledonous and dicotyledonous harmful plants,
(B2) herbicides which are effective selectively in cereals and some dicotyledonous crops against predominantly dicotyledonous harmful plants, and
(B3) herbicides which are to be employed nonselectively or in specifically tolerant crops and are effective against monocotyledonous and dicotyledonous harmful plants.
The herbicide combinations according to the invention can contain other components, e.g. other types of crop protection active substances and/or adjuvants and/or formulation auxiliaries conventionally used in crop protection, or are used together with the latter.
The synergistic effects are observed when the active substances (A) and (B) are applied together, but can also frequently be observed upon split application (splitting). Another possibility is to apply the herbicides or herbicide combinations in several portions (sequential application), for example after pre-emergence applications, followed by post-emergence applications or after early post-emergence applications, followed by applications at medium or late post-emergence. Preferred is the simultaneous or nearly simultaneous application of the active substances of the combination in question.
The synergistic effects allow the application rates of the individual active substances to be reduced, a more potent action with the same application rate, the control of species to which the action has hitherto not extended (zero effect), an extended application period and/or a reduced number of required individual applications and—as a result for the user—economically and ecologically more advantageous weed control systems.
For example, the combinations of (A)+(B) according to the invention allow synergistically increased effects which far and unexpectedly exceed the effects which can be achieved with the individual active substances (A) and (B).
Said formula (I) encompasses all stereoisomers and their mixtures, in particular also racemic mixtures and—if enantiomers are possible—the particular enantiomer which has a biological action. Examples of active substances of the formula (I) are compounds of the formula (A1) and their salts
in which R
3
is defined as in formula (I) and Me is methyl, preferably the compounds (A1.1) to (A1.6)
(A1.1)
N-[N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-
(dimethylaminocarbonyl)-5-(formylamino)benzenesulfonamide,
i.e. formula (A1) where R
3
= hydrogen, and its salts;
(A1.2)
N-[N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-
(dimethylaminocarbonyl)-5-(acetylamino)benzenesulfonamide,
i.e. formula (A1) where R
3
= methyl, and its salts;
(A1.3)
N-[N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-
(dimethylaminocarbonyl)-5-(propionylamino)-
benzenesulfonamide,
i.e. formula (A1) where R
3
= ethyl, and its salts;
(A1.4)
N-[N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-
(dimethylaminocarbonyl)-5-(isopropycarbonylamino)-
benzenesulfonamide,
i.e. formula (A1) where R
3
= isopropyl, and its salts;
(A1.5)
N-[N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-
(dimethylaminocarbonyl)-5-(methoxycarbonylamino)-
benzenesulfonamide,
i.e. formula (A1) where R
3
= methoxy, and its salts;
(A1.6)
N-[N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-
(dimethylaminocarbonyl)-5-(ethoxycarbonylamino)-
benzene

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