3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles

Details 3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles 3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles

2002-05-23

2003-09-02

Ramsuer, Robert W. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S240000

Reexamination Certificate

active

06613719

ABSTRACT:

The present invention relates to certain 3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles and to processes for their preparation, to compositions comprising them and to the use of these derivatives or of the compositions comprising them for controlling harmful plants.
The literature, for example WO 96/26206, WO 98/31682 and WO 98/31681, discloses pyrazol-4-yl-benzoyl derivatives.
The earlier applications WO 00/34273, WO 00/34272, DE 19936520.2 and DE 19936518.0 describe, inter alia, (4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles and their herbicidal properties. They do not describe the compounds of the formula I defined below.
However, the herbicidal properties of the prior-art compounds and their compatibility with crop plants are not 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 3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles of the formula I
in which
R
1
is C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy or C
1
-C
6
-haloalkoxy;
R
2
is C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-haloalkylthio, C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-haloalkylsulfinyl, C
1
-C
6
-alkylsulfonyl or C
1
-C
6
-haloalkylsulfonyl, halogen, cyano or nitro;
R
3
is hydrogen, C
1
-C
6
-alkyl or halogen;
R
4
is C
1
-C
4
-haloalkyl;
R
5
, R
6
, R
7
independently of one another are hydrogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl;
R
8
is hydroxyl, C
1
-C
6
-alkoxy, C
3
-C
6
-alkenyloxy, C
1
-C
6
-alkylsulfonyloxy, C
1
-C
6
-alkylcarbonyloxy, phenyl-C
1
-C
4
-alkoxy, phenylcarbonyl-C
1
-C
4
-alkoxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the four lastmentioned 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
9
is hydrogen or C
1
-C
2
-alkyl; and
R
10
is hydrogen or C
1
-C
4
-alkyl;
and their agriculturally useful salts.
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 can contain one or more chiral centers, in which case they are present as enantiomer or diastereomer mixtures. The invention provides both the pure enantiomers or diastereomers and their mixtures.
Compounds of the formula I may also be present in the form of their agriculturally useful salts, the nature of the salt generally 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 hydrogens may be replaced 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, dimethylammonium, 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, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C
1
-C
4
-alkanoic acids, preferably formate, acetate, propionate and butyrate.
The organic moieties mentioned for the substituents R
1
-R
10
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, alkylsulfinyl, haloalkylsulfinyl, haloalkylthio, alkylsulfonyl, haloalkylsulfonyl, alkenyl, alkenyloxy, phenylalkyl, phenylcarbonylalkyl, phenylalkoxy and phenylcarbonylalkoxy 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 denotes in each case fluorine, chlorine, bromine or iodine.
Examples of other meanings are:
C
1
-C
2
-alkyl, and the alkyl moieties of phenyl-C
1
-C
2
-alkyl and phenylcarbonyl-C
1
-C
2
-alkyl: methyl or ethyl;
C
1
-C
4
-alkyl, and the alkyl moieties of C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkylcarbonyloxy, phenyl-C
1
-C
4
-alkyl and phenylcarbonyl-C
1
-C
4
-alkyl: C
1
-C
2
-alkyl as mentioned above, and also 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
2
-haloalkyl: a C
1
-C
2
-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, bromomethyl, iodomethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 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 or pentafluoroethyl;
C
1
-C
4
-haloalkyl: C
1
-C
2
-haloalkyl as mentioned above, and also, for example, 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
6
-haloalkyl: C
1
-C
4
-haloalkyl as mentioned above, and also, for example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl or dodecafluorohexyl;
C
1
-C
2
-alkoxy as alkoxy moieties of phenyl-C
1
-C
2
-alkoxy and phenylcarbonyl-C
1
-C
2
-alkoxy: methoxy or ethoxy;
C
1
-C
4
-alkoxy, and the alkoxy radicals of phenyl-C
1
-C
4
-alkoxy and phenylcarbonyl-C
1
-C
4
-alkoxy: C
1
-C
2
-alkoxy as mentioned above, and also, for example, 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-methoxylbutoxy, 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-

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