Substituted 1-methyl-3-phenylpyrazoles and the use thereof as he

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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504169, 504282, A01N 4356, C07D23120

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active

059626941

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BRIEF SUMMARY
The present invention relates to new substituted 1-methyl-3-phenylpyrazoles of the formula I ##STR2## where the substituents have the following meanings: R.sup.1 is C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -haloalkylthio; -fluoroalkenyl or --C(R.sup.5)(X-R.sup.6)(Y-R.sup.7), where -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.3 -C.sub.4 -alkenyl, C.sub.3 -C.sub.4 -haloalkenyl or C.sub.3 -C.sub.4 -alkynyl;
Furthermore, the invention relates to of plants, plants which comprise the compounds I as active ingredients, for the desiccation/defoliation of plants using the compounds I, and desiccation/defoliation of plants using the compounds I.
In WO 95/24403, many heterocycles having the common radical --S(O).sub.0-2 --CH.sub.2 CH.sub.2 CH.dbd.CF.sub.2 -- inter alia 4-cyano-5-(4,4-difluorobut-3-enylthio)-1-methyl-3-phenylpyrazole--are reported as having nematicidal, insecticidal and acaricidal properties.
Furthermore, JP-A 03/072 460 describes herbicidally active phenylpyrazole derivatives of the formula II ##STR3## where R.sup.a can be, inter alia, halogen-substituted lower alkoxy or lower alkylthio.
Furthermore, JP-A 03/151 367 discloses, as herbicides, 1-lower-alkyl-3-(2,4-dihalophenyl)-4-halo-5-(haloalkoxy)pyrazoles which have attached to them in the 5-position on the phenyl ring a 1,3-dioxolan-2-yl group, inter alia.
JP 06/199 805 discloses a process for the preparation of herbicidally active 1-H- and 1-lower-alkyl-3-(dihalophenyl)-4-halogen-5-(haloalkoxy/haloalkylthio)pyraz oles which can have attached to them in the 5-position on the phenyl ring halogen or lower alkoxy, inter alia. Moreover, there can be found in JP-A 03/163 063 herbicidally active phenylpyrazoles of the general formula III ##STR4## where R.sup.b can be, inter alia, formyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, lower alkenyloxy, lower alkenylthio, lower haloalkenyloxy, lower haloalkenylthio, lower alkynyloxy or lower alkynylthio.
WO 92/02509 relates to pyrazole derivatives which are substituted by phenyl and alkylsulfonyl and which are also reported as having a herbicidal action. Substances which are suitable for their preparation are, inter alia, compounds of type I.
Other herbicides of the type of the compounds I can also be seen in the earlier WO 95/34659.
Finally, some of the substituted 1-methyl-3-phenylpyrazoles I formally come under the general formulae of the 3-phenylpyrazoles in the earlier Patent Applications WO 96/01255 and WO 96/15115.
However, the herbicidal properties of the prior art phenylpyrazoles with a view to the harmful plants are not always entirely satisfactory. It was therefore the object of the present invention to provide novel herbicidally active 3-phenylpyrazoles which allow better control of undesirable plants. Another object was to provide novel compounds which have a desiccant or defoliant action.
We have found that this object is achieved by the present substituted 1-methyl-3-phenylpyrazoles of the formula I and their herbicidal action. We have furthermore found herbicidal compositions which comprise the compounds I and have a very good herbicidal activity. Moreover, we have found processes for the preparation of these compositions and methods for controlling undesirable vegetation using the compounds I.
We have furthermore found that the compounds I are also suitable for the desiccation/defoliation of parts of plants, suitable plants being crop plants such as cotton, potatoes, oilseed rape, sunflower, soybean or field beans, in particular cotton. Thus, we have found compositions for the desiccation and/or defoliation of plants, processes for the preparation of these compositions and methods for the desiccation and/or defoliation of plants 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 enantiomer or diastereomer mixtures. The invention relates to the pure enantiomers or diastereomers and also to their mixtures.
Agriculturally useful acid addition salts of I are generally

REFERENCES:
patent: 4298749 (1981-11-01), Plath et al.
patent: 4316040 (1982-02-01), Plath et al.
patent: 5077142 (1991-12-01), Sakon et al.
Chem. Abst., vol. 115, No. 5, Aug. 5, 1991.

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