1-cycloalkylpyrazolyl-benzoyl derivatives

Details 1-cycloalkylpyrazolyl-benzoyl derivatives 1-cycloalkylpyrazolyl-benzoyl derivatives

2002-02-06

2004-03-30

Rotman, Alan L. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S247000

Reexamination Certificate

active

06713436

ABSTRACT:

The present invention relates to 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I
where:
X is O, NR
6
or CR
7
R
8
;
Y is O, S, NR
9
or CR
10
R
11
;
R
1
is nitro, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, C
1
-C
4
-alkylsulfonyl or C
1
-C
4
-haloalkylsulfonyl;
R
2
,R
3
,R
7
,R
8
,R
10
,R
11
are hydrogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl;
or
R
3
and R
6
or R
3
and R
8
or R
3
and R
9
or R
3
and R
11
together form a bond;
R
4
is halogen, nitro, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, C
1
-C
4
-alkylsulfonyl or C
1
-C
4
-haloalkylsulfonyl;
R
5
is hydrogen, halogen or C
1
-C
4
-alkyl;
R
6
,R
9
are hydrogen or C
1
-C
6
-alkyl;
R
12
is hydroxyl, C
1
-C
6
-alkoxy, C
3
-C
6
-alkenyloxy, C
1
-C
6
-alkylsulfonyloxy, C
1
-C
6
-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-haloalkoxy;
R
13
is a cyclic ring system containing 3 to 14 ring atoms which may be partially or fully halogenated and/or may carry one to three of the following groups: C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkyl or C
1
-C
4
-haloalkoxy;
R
14
is hydrogen or C
1
-C
4
-alkyl;
and their agriculturally useful salts.
Moreover, the invention relates to processes for preparing compounds of the formula I, to compositions comprising them and to the use of these derivatives or of compositions comprising them for controlling harmful plants.
Cycloalkyl-substituted pyrazolylbenzoyl derivatives which are substituted in the 3-position of the benzoyl radical by an N-bonded heterocycle or by phenyl are disclosed in the literature, for example in WO 98/42678 and WO 98/52926.
However, the herbicidal properties of the prior art compounds and their compatibility with crop plants may not be entirely satisfactory.
It is an object of the present invention to provide novel, in particular herbicidally active, compounds having improved properties.
We have found that this object is achieved by the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I and their herbicidal action.
Furthermore, we have found herbicidal compositions which comprise the compounds I and have very good herbicidal action. Moreover, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.
Depending on the substitution pattern, the compounds of the formula I may contain one or more chiral centers, in which case they are present as enantiomers or mixtures of diastereomers. The invention provides both the pure enantiomers or diastereomers and their mixtures.
The compounds of the formula I can also be present in the form of their agriculturally useful salts, the kind of salt usually being immaterial. In general, the salts of those cations or the acid addition salts of those acids are suitable whose cations and anions, respectively, do not adversely affect the herbicidal action of the compounds I.
Suitable cations are, in particular, ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium, where, if desired, one to four hydrogen atoms may be replaced here by C
1
-C
4
-alkyl, hydroxy-C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, hydroxy-C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, phenyl or benzyl, preferably ammonium, dimethylassonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C
1
-C
4
-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C
1
-C
4
-alkyl)sulfoxonium.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C
1
-C
4
-alkanoic acids, preferably formate, acetate, propionate and butyrate.
The organic molecular moieties mentioned for the substituents R
1
-R
12
or as radicals on phenyl rings are collective terms for individual enumerations of the individual group members. All hydrocarbon chains, i.e. all alkyl, alkylcarbonyl, haloalkyl, alkoxy, haloalkoxy, alkylcarbonyloxy, alkylsulfonyloxy, alkylthio, haloalkylthio, alkylsulfonyl, haloalkylsulfonyl, alkenyl and alkenyloxy moieties can be straight-chain or branched. Unless indicated otherwise, halogenated substituents preferably carry one to five identical or different halogen atoms. The term halogen represents in each case fluorine, chlorine, bromine or iodine.
Examples of other meanings are:
C
1
-C
4
-alkyl, and the alkyl moieties of C
1
-C
4
-alkylcarbonyl and C
1
-C
4
-alkylcarbonyloxy: for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;
C
1
-C
6
-alkyl, and the alkyl moieties of C
1
-C
6
-alkylcarbonyl and C
1
-C
6
-alkylcarbonyloxy: C
1
-C
4
-alkyl as mentioned above, and also, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 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-ethyl-1-methylpropyl and 1-ethyl-3-methylpropyl;
C
1
-C
4
-haloalkyl: a C
1
-C
4
-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoramethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromoethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl and nonafluorobutyl;
C
1
-C
4
-alkoxy: for example methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy;
C
1
-C
6
-alkoxy: C
1
-C
4
-alkoxy as mentioned above, and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy;
C
1
-C
4
-haloalkoxy: a C
1
-C
4
-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2

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