Benzisoxazole derivatives and pesticidal compositions containing

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

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548241, A61K 3142, C07D26356

Patent

active

057863741

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BRIEF SUMMARY
This application is a 371 of PCT/EP95/04154 filed Oct. 23, 1995.
The present invention relates to compounds of formula ##STR1## wherein a) X is CH, Z is oxygen and W is OR.sub.1 ; or NHR.sub.1 group; and the other substituents have the following meanings: -C.sub.4 alkynyl; cyclopropyl, C.sub.1 -C.sub.4 alkoxymethyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio or CN; alkyl, C.sub.1 -C.sub.4 alkoxy, OH, CN, NO.sub.2, Si(CH.sub.3).sub.3, CF.sub.3 or halogen; unsubstituted or mono- to tetrasubstituted C.sub.1 -C.sub.4 alkylenedioxy, the substituents being selected from the group consisting of C.sub.1 -C.sub.4 alkyl and halogen; CN, NO.sub.2, XR6, phenyl or chlorophenyl; S(O).sub.m, S(O).sub.m (C.sub.1 -C.sub.4 alkylene), (C.sub.1 -C.sub.4 alkylene)S(O).sub.m or C.sub.1 -C.sub.4 alkylene; -C.sub.6 cycloalkyl; CN; C.sub.1 -C.sub.4 alkylene-Si(C.sub.1 -C.sub.4 alkyl).sub.3 ; C.sub.2 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 alkynyl which are each unsubstituted or substituted by 1 to 3 halogen atoms, or mono- to pentasubstituted aryl or heterocyclyl, the substituents being selected from the group consisting of halogen, C.sub.1 -C.sub.6 alkyl, halo-C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halo-C.sub.1 -C.sub.6 alkoxy and CN; or ##STR2## and wherein R.sub.7, R8, R.sub.9, R.sub.10 and R.sub.11 are each independently of one another H, halogen or C.sub.1 -C.sub.4 alkyl;
The invention further relates to a process for the preparation of, and to the use of, these compounds and E/Z isomers, to fungicidal and pesticidal compositions whose active ingredient is selected from said compounds and E/Z isomers, and to the preparation and use of said compositions.
Certain methoxyacrylic acid derivatives have been proposed in the literature for use as insecticidal and fungicidal compounds in pesticidal compositions. The biological properties of these known compounds, however, are not satisfactory in all respects in the field of pest control and fungicides, so that there is a need to provide further compounds having pesticidal properties, especially for controlling insects and representatives of the order Acarina, and fungicidal properties, especially for controlling phytopathogenic fungi. This object is achieved in the practice of this invention with the compounds of formula I.
Some compounds of formula I contain asymmetrically substituted carbon atoms, so that the compounds are obtained in optically active form. Owing to the presence of the olefinic and oximino double bonds, the compounds are obtained in the form of E and Z isomers. Furthermore, atropo-isomers of the compounds may also be obtained. Formula I will therefore be understood as encompassing all these possible isomeric forms as well as their mixtures, for example racemates and any mixtures of E/Z isomers.
Unless otherwise defined, the general terms employed throughout this specification have the meanings given hereinafter.
Unless otherwise defined, carbon-containing groups and compounds each contain from 1 to 6, preferably from 1 to 4, carbon atoms inclusive, and preferably contain 1 or 2 carbon atoms.
Alkyl as group per se as well as structural unit of other groups and compounds, as of haloalkyl, alkoxy and alkylthio, is either in straight-chain configuration, typically methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl, or in branched-chain configuration, typically isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl or isooctyl.
Alkenyl as group per se as well as structural unit of other groups and compounds, as of haloalkenyl, is either in straight-chain configuration, typically vinyl, 1-methylvinyl, allyl or 1-butenyl, or in branched-chain configuration, typically isopropenyl.
Alkynyl as group per se as well as structural unit of other groups and compounds, as of haloalkynyl, is either in straight-chain configuration, typically propargyl, 2-butynyl or 5-hexynyl, or in branched-chain configuration, typically 2-ethynylpropyl or 2-propargylisopropyl.
C.sub.3 -C.sub.6 Cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
Aryl

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