Herbicidal compositions

Details Herbicidal compositions Herbicidal compositions

2000-10-24

2003-05-27

Clardy, S. Mark (Department: 1616)

Plant protecting and regulating compositions

Antidotes

C504S106000, C504S214000, C504S362000

Reexamination Certificate

active

06569805

ABSTRACT:

The invention lies in the technical field of the crop protection products; in particular, the invention relates to herbicidal compositions comprising certain phenylsulfonylureas and/or their salts and vegetable oils which are outstandingly suitable for controlling harmful plants in crops.
The use of sulfonylureas as active component of crop protection products is known (for example EP-A-007 687, EP-A-030 138). Likewise, it is known to combine sulfonylureas such as Nicosulfuron (Accent®) with vegetable oils (for example CPR/T & OR 1999 Adjuvant Reference Supplement-C&P Press 1998, p. 55/56).
The object of the present invention was to provide herbicidal compositions which exhibit a particularly high herbicidal activity, selective properties toward agricultural crop plants and also a high crop plant tolerance.
Surprisingly, it has now been found that this object is achieved by herbicidal compositions which comprise specific sulfonylureas in combination with vegetable oils.
The present invention thus relates to herbicidal compositions comprising
A) one or more sulfonylureas of the formula (I) and/or their salts
 in which
R
1
is C
2
-C
4
-alkoxy or CO—R
a
, where R
a
equals OH, C
1
-C
4
-alkoxy or NR
b
R
c
,in which R
b
and R
c
independently of one another are identical or different and are H or C
1
-C
4
-alkyl,
R
2
is halogen or (A)
n
—NR
d
R
e
, in which n equals zero or 1, A is a group CR′R″, in which R′ and R″ independently of one another are identical or different and are H or C
1
-C
4
-alkyl, R
d
equals H or C
1
-C
4
-alkyl and R
e
is an acyl radical and, in the event that R
1
equals C
2
-C
4
-alkoxy, R
2
may also be H,
R
3
is H or C
1
-C
4
-alkyl,
m equals zero or 1, preferably zero,
X and Y independently of one another are identical or different and are C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy or C
1
-C
6
-alkylthio, each of the three radicals mentioned 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, or are C
3
-C
6
-cycloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
3
-C
6
-alkenyloxy or C
3
-C
6
-alkynyloxy, preferably C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy,
Z equals CH or N, and
B) one or more vegetable oils.
The compounds of the formula (I) can form salts in which the hydrogen of the —SO
2
—NH— group is replaced by an agriculturally suitable cation. Examples of these salts are metal salts, in particular alkali metal salts (for example sodium or potassium salts) or alkaline-earth metal salts, or else ammonium salts or salts with organic amines. Equally, salt formation can take place by subjecting a strong acid to an addition reaction with the heterocyclic moiety of the compounds of the formula (I). Suitable examples are HCl, HNO
3
, trichloroacetic acid, acetic acid or palwithic acid. Especially advantageous compounds are those in which the salt of the herbicide of the formula (I) is formed by replacing the hydrogen of the —SO
2
—NH— group by a cation selected from the group consisting of the alkali metals, alkaline-earth metals and ammonium, preferably sodium.
As long as the compounds of the formula (I) contain one or more asymmetric carbon atoms or else double bonds which are not specifically mentioned in the formula, they are still encompassed by the formula (I). The stereoisomers which are possible and which are defined by their specific spatial shape, such as enantiomers, diastereoisomers, Z- and E-isomers, are all encompassed by the formula (I) and can be obtained by customary methods from mixtures of the stereoisomers or else prepared by stereoselective reactions in combination with the use of stereochemically pure starting materials. The abovementioned stereoisomers in pure form and also their mixtures can thus be employed in accordance with the invention.
An acyl radical for the purposes of the present description means the radical of an organic acid which is formed formally by eliminating an OH group from the organic acid, for example the radical of a carboxylic acid and radicals of acids derived therefrom such as thiocarboxylic acid, optionally N-substituted iminocarboxylic acids or the radicals of carbonic monoesters, optionally N-substituted carbamic acids, sulfonic acids, sulfinic acids, phosphonic acids, phosphinic acids.
An acyl radical is preferably formyl or acyl selected from the group consisting of CO—R
X
, CS—R
X
, CO—OR
X
, CS—OR
X
, CS—SR
X
, SOR
Y
or SO
2
R
Y
, where R
X
and R
Y
are in each case a C
1
-C
10
-hydrocarbon radical such as C
1
-C
10
-alkyl or C
6
-C
10
-aryl which is unsubstituted or substituted, for example by one or more substituents selected from the group consisting of halogen such as F, Cl, Br, I, alkoxy, haloalkoxy, hydroxyl, amino, nitro, cyano or alkylthio, or R
X
and R
Y
are aminocarbonyl, or aminosulfonyl, the two last-mentioned radicals being unsubstituted, N-monosubstituted or N,N-disubstituted, for example by substituents selected from the group consisting of alkyl or aryl.
Acyl is, for example, formyl, haloalkylcarbonyl, alkylcarbonyl such as (C
1
-C
4
)alkylcarbonyl, phenylcarbonyl, it being possible for the phenyl ring to be substituted, or is alkyloxycarbonyl, such as (C
1
-C
4
) alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, such as (C
1
-C
4
) alkylsulfonyl, alkylsulfinyl, such as C
1
-C
4
(alkylsulfinyl), N-alkyl-1-iminoalkyl, such as N-(C
1
-C
4
)-1-imino-(C
1
-C
4
)alkyl and other radicals of organic acids. For the purposes of the present description, the radicals alkyl and alkyl-containing radicals such as alkoxy and alkylthio and the corresponding unsubstituted and/or substituted radicals in the carbon skeleton are in each case straight-chain or branched. Unless otherwise specified, the lower carbon skeletons, for example those having 1 to 4 carbon atoms, are preferred for these radicals. Alkyl radicals, also in the composite meanings such as alkoxy, or alkylthio are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls, such as n-heptyls, 1-methylhexyl and 1,4-dimethylpentyl.
While sulfonylureas of the formula (I) and their salts are known in principle (see, for example, EP-A-342 569, EP-A-574 418, EP-A-723 534 and EP-A-757 679, which are expressly referred to herewith), their outstanding suitability as components in combinations in, preferably, synergistic mixtures with vegetable oils cannot be seen from the prior art.
Preferred sulfonylureas are those of the formula (I) and/or their salts in which
m equals 1,
R
1
is C
2
-C
4
-alkoxy and R
2
equals H.
Likewise preferred sulfonylureas of the formula (I) and/or their salts are those in which
m equals 0, and
a) R
1
equals CO—(C
1
-C
4
-alkoxy) and R
2
equals halogen, preferably iodine, or R
2
equals CH
2
—NHR
e
, in which R
e
is an acyl radical, preferably C
1
-C
4
-alkylsulfonyl, or
b) R
1
equals CO—N(C
1
-C
4
-alkyl)
2
and R
2
equals NHR
e
, in which R
e
is an acyl radical, preferably formyl.
Examples of compounds of the formula (I) and/or their salts which may be mentioned are:
A1=N-(4,6-dimethoxypyrimidin-2-ylaminocarbonyl)-2-methoxycarbonyl-5-acetylaminobenzenesulfonamide
A2=N-(4,6-dimethoxypyrimidin-2-ylaminocarbonyl)-2-methoxycarbonyl-5-(N-formyl-N-methylaminomethyl)benzenesulfonamide sodium salt
A3=N-(4,6-dimethoxypyrimidin-2-ylaminocarbonyl)-2-methoxycarbonyl-5-acetylamino)benzenesulfonamide sodium salt
A4=N-(4,6-dimethoxypyrimidin-2-ylaminocarbonyl2-methoxycarbonyl-5-(N-methyl-N-propionylamino)benzenesulfonamide sodium salt
A5=N-(4,6-dimethoxypyrimidin-2-ylaminocarbonyl2-methoxycarbonyl-5-(N-isopropionylmethylamino)benzenesulfonamide sodium salt
A6=N-(4,6-dimethoxypyrimidin-2-ylaminocarbonyl2-methoxycarbonyl-5-(N-methoxycarbonylaminomethyl)benzenesulfonamide sodium salt
A7=N-(4,6-dimethoxypyrimidin-2-ylaminocarbonyl)-2-(N,N-dimethyl-aminocarbonyl)-5-(N-methoxycarbonylamino)benzenesulfonamide sodium salt
A8=N-(4,6-dimethoxypyrimidin-2-ylaminocar

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