Isoxazole- and isothiazole-5-carboxamides

An isoxazole- or isothiazole-5-carboxamide of the formula I ##STR353## where X is oxygen or sulfur;

• R.sup.1 is hydrogen, C.sub.1 -C.sub.6 -alkyl which can carry from one to five halogen atoms and/or one or two of the following:
• C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -haloalkoxy, cyano or phenyl which can be up to trisubstituted by halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -haloalkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -haloalkoxy, cyano or nitro;
• C.sub.3 -C.sub.8 -cycloalkyl-substituted C.sub.1 -C.sub.6 -alkyl;
• C.sub.3 -C.sub.8 -cycloalkyl or C.sub.3 -C.sub.6 -cycloalkenyl, each of which can be mono- to trisubstituted by C.sub.1 -C.sub.4 -alkyl or halogen;
• C.sub.2 -C.sub.6 -alkenyl whose double bond can be epoxidized, or C.sub.2 -C.sub.6 -alkynyl, where both groups can be mono- to trisubstituted by halogen, C.sub.1 -C.sub.3 -alkoxy and/or monosubstituted by cyclopropyl or phenyl, where the phenyl can additionally carry up to three of the following substituents:
• C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, halogen, cyano or nitro;
• C.sub.1 -C.sub.4 -alkoxy;
• a 5- or 6-membered heterocyclic radical with one or two hetero atoms selected from oxygen, sulfur and nitrogen, which can carry one or two of the following substituents:
• C.sub.1 -C.sub.3 -alkyl, halogen, C.sub.1 -C.sub.3 -alkoxy, carboxyl or C.sub.1 -C.sub.3 -alkoxycarbonyl;
• phenyl which can carry from one to three of the following:
• C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -haloalkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -haloalkoxy, C.sub.1 -C.sub.3 -alkylthio, C.sub.1 -C.sub.3 -haloalkylthio, halogen, nitro and cyano,
• R.sup.2 is COYR.sup.5, where
• Y is oxygen or sulfur
• R.sup.5 is C.sub.3 -C.sub.6 -haloalkynyl or C.sub.1 -C.sub.4 -alkyl which carries --CR.sup.10 .dbd.N--R.sup.11 where R.sup.10 is hydrogen or C.sub.1 -C.sub.6 -alkyl and R.sup.11 is C.sub.1 -C.sub.6 -alkoxy, C.sub.3 -C.sub.6 -alkenyloxy or C.sub.3 -C.sub.6 -alkynyloxy, each of which can carry up to three halogen atoms and/or one phenyl with, if desired, up to three of the following:
• halogen, nitro, cyano, C.sub.1 -C.sub.3 -alkyl or C.sub.1 -C.sub.3 -alkoxy;
• phenoxy which can carry up to three of the following substituents:
• halogen, nitro, cyano, C.sub.1 -C.sub.3 -alkyl or C.sub.1 -C.sub.3 -alkoxy;
• C.sub.1 -C.sub.3 -alkylamino, di(C.sub.1 -C.sub.6 -alkyl) amino or phenylamino, where the aromatic ring can carry up to three of the following:
• halogen, nitro, cyano, C.sub.1 -C.sub.3 -alkyl or C.sub.1 -C.sub.3 -alkoxy;
• R.sup.3 is hydrogen;
• C.sub.1 -C.sub.6 -alkyl which can carry from one to three of the following substituents:
• hydroxyl, halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio or di-(C.sub.1 -C.sub.4)-alkylamino;
• C.sub.3 -C.sub.8 -cycloalkyl which can be mono- to trisubstituted by halogen, C.sub.1 -C.sub.4 -alkyl and partially or completely halogenated C.sub.1 -C.sub.4 -alkyl;
• R.sup.4 is hydrogen, hydroxyl, C.sub.1 -C.sub.4 -alkoxy;
• C.sub.1 -C.sub.6 -alkyl which can carry from one to three of the following:
• halogen, cyano, C.sub.1 -C.sub.4 -alkoxy, partially or completely halogenated C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, partially or completely halogenated C.sub.1 -C.sub.4 -alkylthio, di-C.sub.1 -C.sub.4 -alkylamino, C.sub.3 -C.sub.8 -cycloalkyl or phenyl, where the phenyl ring in turn can carry one to three of the following:
• halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, partially or completely halogenated C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio or partially or completely halogenated C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio;
• C.sub.3 -C.sub.8 -cycloalkyl which can carry from one to three of the following:
• halogen, nitro, cyano, C.sub.1 -C.sub.6 -alkyl, partially or completely halogenated C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy or partially or completely halogenated C.sub.1 -C.sub.4 -alkoxy;
• C.sub.3 -C.sub.6 -alkenyl whose double bond can be epoxidized, or C.sub.3 -C.sub.6 -alkynyl, each of which can be mono- to trisubstituted by halogen and/or monosubstituted by phenyl, where the phenyl in turn can carry from one to three of the following:
• C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -halo-alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, halogen, cyano or nitro;
• di-(C.sub.1 -C.sub.4)-alkylamino;
• a 5- or 6-membered heterocyclic, saturated or aromatic radical with one or two hetero atoms selected from oxygen, sulfur and nitrogen, which can be mono- to trisubstituted by C.sub.1 -C.sub.4 -alkyl or halogen;
• phenyl which can carry from one to four of the following:
• C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, halogen, nitro, cyano, formyl, C.sub.2 -C.sub.4 -alkanoyl, C.sub.2 -C.sub.4 -haloalkanoyl or C.sub.1 -C.sub.4 -alkoxycarbonyl;
• naphthyl which can be mono- to trisubstituted by C.sub.1 -C.sub.4 -alkyl or halogen;
• or
• R.sup.3 and R.sup.4 together form a tetra- to heptamethylene chain which can be interrupted by oxygen, sulfur or N-methyl, or --(CH.sub.2).sub.3 --CO--, with the proviso that R.sup.5 is not C.sub.3 -C.sub.8 -haloalkynyl when R.sup.1 is unsubstituted or substituted C.sub.2 -C.sub.6 -alkenyl, whose double bond can be epoxidized, unsubstituted or substituted C.sub.3 -C.sub.6 -cycloalkenyl, unsubstituted or substituted C.sub.2 -C.sub.6 -alkynyl or C.sub.3 -C.sub.8 -cycloalkyl-substituted C.sub.1 -C.sub.6 -alkyl;
• and the environmentally acceptable salts of the compound I.