Pyridine-2,3-dicarboxylic acid diamides

Details Pyridine-2,3-dicarboxylic acid diamides Pyridine-2,3-dicarboxylic acid diamides

2001-09-28

2002-10-29

Davis, Zinna Northington (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C546S336000, C546S337000

Reexamination Certificate

active

06472349

ABSTRACT:

The present invention relates to pyridine-2,3-dicarboxamides of the formula I
where:
R
1
is halogen, CN, NO
2
, C
1
-C
3
-alkyl, C
1
-C
3
-haloalkyl, C
1
-C
3
-alkoxy, C
1
-C
3
-haloalkoxy, C
1
-C
3
-alkylthio, C
1
-C
3
-haloalkylthio, C
1
-C
3
-alkylsulfinyl, C
1
-C
3
-haloalkylsulfinyl, C
1
-C
3
-alkylsulfonyl, C
1
-C
3
-haloalkylsulfonyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkyl-C
1
-C
3
-alkyl, C
2
-C
4
-alkenyl, C2-C
4
-haloalkenyl, C
2
-C
4
-alkynyl, C
3
-C
4
-haloalkynyl, amino, C
1
-C
3
-monoalkylamino or C
1
-C
3
-alkylcarbonyl;
Q is one of the radicals Q
1
-Q
7
R
2
is halogen, CN, NO
2
, formyl, carbamoyl, C
1
-C
4
-alkylcarbonyl, C
1
-C
3
-alkoximinomethyl, C
1
-C
3
-alkyl, C
1
-C
3
-haloalkyl, C
1
-C
3
-alkoxymethyl, C
1
-C
3
-alkoxy, C
1
-C
3
-haloalkoxy, C
1
-C
3
-alkoxycarbonyl, C
1
-C
3
-alkylthiocarbonyl, C
1
-C
3
-alkylcarbamoyl or C
1
-C
3
-alkoxycarbonyl-C
1
-C
3
-alkoxy, C
3
-C
4
-alkenyloxy, C
3
-C
4
-haloalkenyloxy, C
3
-C
4
-alkynyloxy, C
3
-C
4
-haloalkenyloxy, C
1
-C
3
-alkylthio, C
1
-C
3
-haloalkylthio, C
1
-C
3
-alkylsulfinyl, C
1
-C
3
-haloalkylsulfinyl, C
1
-C
3
-alkylsulfonyl or C
1
-C
3
-haloalkylsulfonyl;
R
3
is halogen, CN, NO
2
, C
1
-C
3
-alkyl, C
1
-C
3
-alkoxy, C
1
-C
3
-haloalkyl or C
1
-C
3
-haloalkoxy;
R
4
is hydrogen, C
1
-C
3
-alkyl, C
1
-C
3
-haloalkyl, C
1
-C
3
-alkoxy, saturated or unsaturated C
3
-C
7
-cycloalkyl, 3- to 7-membered saturated or unsaturated heterocyclyl having 1, 2 or 3 heteroatoms selected independently of one another from the group consisting of N, O and S, where each cycloalkyl and/or heterocyclyl ring may be unsubstituted or have 1 or 2 substituents selected independently of one another from the group consisting of halogen, C
1
-C
3
-alkyl, C
1
-C
3
-haloalkyl or C
1
-C
3
-alkoxy;
R
5
is hydrogen, C
1
-C
3
-alkyl, OH or C
1
-C
4
-alkoxy;
R
6
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-cyanoalkyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkenyl, C
3
-C
6
-cycloalkyl-C
1
-C
3
-alkyl, C
3
-C
6
-cycloalkyl having 1 or 2 substituents which are selected independently of one another from the group consisting of halogen and C
1
-C
3
-alkyl, is C
3
-C
6
-cycloalkoxy-C
1
-C
3
-alkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
1
-C
6
-alkylthio-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxycarbonyl-C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, amino, C
1
-C
4
-monoalkylamino, di-C
1
-C
4
-alkylamino or R
6
together with R
5
is a 5- or 6-membered heterocycle having 1, 2 or 3 heteroatoms which are selected independently of one another from the group consisting of N, O and S, and which is unsubstituted or has 1 or 2 substituents selected independently of one another from the group consisting of halogen, C
1
-C
3
-alkyl, C
1
-C
3
-alkoxy and C
1
-C
3
-haloalkyl;
X is O or S;
m is 0 or 1;
n is 0, 1, 2 or 3;
o is 0, 1, 2, 3, 4 or 5;
p is 0, 1, 2, 3 or 4;
q is 0, 1, 2 or 3,
where n is 2 or 3 if Q is Q
1
,
and salts thereof, in particular to the agriculturally useful salts of the compounds of the formula I.
Moreover, the invention relates to
the use of the compounds I as herbicides,
herbicidal compositions comprising the compounds I as active substances,
methods for controlling undesirable plant growth using the compounds I.
EP 799 825 A describes certain pyridine-2,3-dicarboxamides for use as herbicides.
It is an object of the present invention to provide novel herbicidally active pyridine-2,3-dicarboxamides which allow better selective control of undesirable plants than the known pyridine-2,3-dicarboxamides.
We have found that this object is achieved by the abovementioned pyridine-2,3-dicarboxamides of the formula I.
Furthermore, we have found herbicidal compositions which comprise these compounds and have very good herbicidal activity. Moreover, we have found methods for controlling undesirable vegetation using the compounds I.
Depending on the substitution pattern, the compounds of the formula I can contain one or more chiral centers, in which case they exist in the form of enantiomers or diastereomer mixtures. The invention provides both the pure enantiomers and diastereomers and mixtures thereof.
Suitable agriculturally useful salts are, in particular, the acid addition salts with those acids whose anions do not adversely affect the herbicidal activity of the compounds of the formula I.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C
1
-C
4
-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds of the formula I with an acid of the appropriate anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
The organic molecular moieties mentioned in the definition of the substituents R
1
to R
6
or as radicals on saturated cycloalkyl or saturated heterocyclic rings are—like the term halogen—collective terms for individual listings of the individual group members. All hydrocarbon chains, i.e. all alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cyanoalkyl, aminoalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkoxycarbonyl and alkoxycarbonylalkoxy radicals, etc., can be straight-chain or branched. Halogenated substituents preferably carry 1, 2, 3, 4 or 5 identical or different halogen atoms. The term halogen represents in each case fluorine, chlorine, bromine and iodone, preferably fluorine and chlorine.
Examples of particular meanings are:
C
1
-C
3
-alkyl: methyl, ethyl, n-propyl, 1-methylethyl;
C
1
-C
4
-alkyl: C
1
-C
3
-alkyl as mentioned above, and also n-butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;
C
1
-C
6
-alkyl: C
1
-C
4
-alkyl as mentioned above, and also n-pentyl, 1-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;
(C
1
-C
3
-alkyl)carbonyl: methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, 1-methylethylcarbonyl; in particular methylcarbonyl, ethylcarbonyl or 1-methylethylcarbonyl;
C
2
-C
4
-alkenyl: eth-1-en-1-yl, prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, n-buten-1-yl, n-buten-2-yl, n-buten-3-yl, 1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl and 2-methylprop-2-en-1-yl;
C
3
-C
6
-alkenyl: C
3
-C
4
-alkenyl as mentioned above, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1-methylbut-1-en-1-yl, 2-methyl-but-1-en-1-yl, 3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, n-hex-1-en-2-yl, n-hex-1-en-1-yl, n-hex-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4-en-1-yl, n-hex-5-en-1-yl, 1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethyl-but-1-en-1-yl, 1-ethylbut-

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