Cyclopropyl-anellated...

Details Cyclopropyl-anellated... Cyclopropyl-anellated...

2002-05-23

2003-09-30

Qazi, Sabiha (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S280000, C504S282000

Reexamination Certificate

active

06627581

ABSTRACT:

The present invention relates to certain cyclopropyl-fused 3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles and to intermediates and processes for their preparation, to compositions comprising them and to the use of these derivatives or 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. Derivatives having fused cycloalkane rings have not been described.
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 cyclopropyl-fused 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, C
1
-C
6
-haloalkoxy, halogen or nitro;
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, C
1
-C
6
-haloalkylsulfonyl, halogen, cyano or nitro;
R
3
is hydrogen, C
1
-C
6
-alkyl or halogen;
R
4
is hydrogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl;
R
5
may have the meanings given for R
4
; or
R
4
, R
5
together are a C
1
-C
4
-alkanediyl group which may be partially or fully halogenated and/or may carry one to three C
1
-C
4
-alkyl groups;
R
6
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, 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
l
-C
4
-alkoxy or C
1
-C
4
-haloalkoxy;
R
7
is hydrogen, C
1
-C
6
-alkyl or cyclopropyl;
R
8
is hydrogen, C
1
-C
6
-alkyl or C
1
-C
6
-haloalkyl; and their agriculturally useful salts.
Furthermore, we have found herbicidal compositions which comprise the compounds I and have very good herbicidal activity. 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 centers of chirality, in which case they are present as enantiomer or diastereomer mixtures. 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 nature of the salt generally being immaterial. In general, the salts of those cations and 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, the alkaline earth metals, preferably calcium and magnesium, 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
-R8 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, alkylsulfinyl, haloalkylsulfinyl, 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
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: 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, 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, 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
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 and 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-2-meth

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