Oxime ethers and fungicides containing them

A method of combating fungi, wherein the fungi, or the materials, plants or seed threatened by fungus attack, or the soil are treated with a fungicidally effective amount of an oxime ether of the formula I ##STR75## where G is C.dbd.W or C(V)R.sup.8,

• W is oxygen or NR.sup.5,
• V is OR.sup.6 or NR.sup.5 R.sup.7,
• R.sup.5 is hydrogen, hydroxyl, NH.sub.2, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.4 -aralkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylamino or C.sub.1 -C.sub.4 -dialkylamino,
• R.sub.6,R.sup.7 is hydrogen, C.sub.1 -C.sub.8 -alkyl or C.sub.1 -C.sub.4 -alkanoyl,
• R.sup.8 is hydrogen or C.sub.1 -C.sub.8 -alkyl,
• R is C.sub.2 -C.sub.8 -alkenyl, C.sub.2 -C.sub.8 -alkynyl, phenyl, hetaryl or --CR.sup.2 R.sup.3 R.sup.4,
• R.sup.2,R.sup.4 are each hydrogen, C.sub.1 -C.sub.8 -alkyl, arylalkyl, hetarylalkyl, alkoxyalkyl, aryloxyalkyl, aryl or hetaryl, or
• R.sup.2,R.sup.4 together with the carbon atom of which they are substituents form a C.sub.3 -C.sub.8 -cycloalkyl ring,
• R.sup.3 is hydrogen, methyl, cyano, carboxyl or C.sub.1 -C.sub.8 -alkoxycarbonyl, or
• R.sup.2,R.sup.3 together with the carbon atom of which they are substituents form a 5-membered to 8-membered
• lactone ring,
• R.sup.1 is C.sub.1-C.sub.8 -alkyl,
• X are nitro, cyano, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -haloalkyl, and
• m is an integer of from 0, 1, 2, 3 or 4, where the radicals X may be identical or different when m is >1,
• is O, S(O).sub.n (n=0, 1 or 2), --O--CO--, --CO--O--, azo, carbonylamino, aminocarbonyl, aminocarbonyloxy, C.sub.1 -C.sub.8 -alkylene, C.sub.2 -C.sub.8 -alkenylene, C.sub.2 -C.sub.8 -alkynylene, C.sub.1 -C.sub.8 -alkylenoxy, oxy-C.sub.2 -C.sub.4 -alkylene, C.sub.1 -C.sub.8 -thioalkylene, oxycarbonyl-C.sub.1 -C.sub.8 -alkylene, carbonyloxy-C.sub.1 -C.sub.8 -alkylene, oxy-C.sub.2 -C.sub.8 -alkylenoxy, oxy-C.sub.2 -C.sub.8 -alkenylene, C.sub.1 -C.sub.8 -alkylamino, carbonyl-C.sub.1 -C.sub.8 -alkylamino, C.sub.1 -C.sub.8 -alkylaminocarbonyl, C.sub.1 -C.sub.8 -alkylaminocarbonyloxy, oxyimino or iminooxyalkylene, is C.sub.1 -C.sub.18 -alkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.10 -alkyl, C.sub.1 -C.sub.10 -haloalkyl, C.sub.2 -C.sub.18 -alkenyl, C.sub.3 -C.sub.8 -alkynyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, aryl, aryl-C.sub.1 -C.sub.10 -alkyl, aryl-C.sub.2 -C.sub.10 -alkenyl, aryloxy-C.sub.1 -C.sub.10 -alkyl or hetaryl,
• where the radicals Z may be unsubstituted or substituted by cyano, formyl, nitro, halogen, 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 -alkyl, C.sub.1 -C.sub.4 -dialkoxy-C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -haloalkenyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, unsubstituted or substituted C.sub.1 -C.sub.10 -alkoxyimino, C.sub.2 -C.sub.10 -alkenyloxyimino, aralkyloxyimino, unsubstituted or substituted C.sub.2 -C.sub.10 -alkanoyl, unsubstituted or substituted phenyl or phenoxy, or are an unsubstituted or substituted carbon-bonded 5-membered heterocyclic structure which contains from one to four identical or different heteroatoms selected from nitrogen, oxygen or sulfur, in which two adjacent substituents may form an unsubstituted or substituted aromatic or heteroaromatic ring.

A fungicide containing an inert carrier and a fungicidally effective amount of an oxime ether of the formula I ##STR76## G is C.dbd.W or C(V)R.sup.8, W is oxygen or NR.sup.5,

• V is OR.sup.6 or NR.sup.5 R.sup.7,
• R.sup.5 is hydrogen, hydroxyl, NH.sub.2, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.4 -aralkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylamino or C.sub.1 -C.sub.4 -dialkylamino,
• R.sup.6,R.sup.7 is hydrogen, C.sub.1 -C.sub.8 -alkyl or C.sub.1 -C.sub.4 -alkanoyl,
• R.sup.8 is hydrogen or C.sub.1 -C.sub.8 -alkyl,
• R is C.sub.2 -C.sub.8 -alkenyl, C.sub.2 -C.sub.8 -alkynyl, phenyl, hetaryl or --CR.sup.2 R.sup.3 R.sup.4,
• R.sup.2,R.sup.4 are each hydrogen, C.sub.1 -C.sub.8 -alkyl, arylalkyl, hetarylalkyl, alkoxyalkyl, aryloxyalkyl, aryl or hetaryl, or
• R.sup.2,R.sup.4 together with the carbon atom of which they are substituents form a C.sub.3 -C.sub.8 -cycloalkyl ring,
• R.sup.3 is hydrogen, methyl, cyano, carboxyl or C.sub.1 -C.sub.8 -alkoxycarbonyl, or
• R.sup.2,R.sup.3 together with the carbon atom of which they are substituents form a 5-membered to 8-membered lactone ring,
• R.sup.1 is C.sub.1 -C.sub.8 -alkyl,
• X are nitro, cyano, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -haloalkyl, and
• m is an integer of from 0, 1, 2, 3 or 4, where the radicals X may be identical or different when m is >1,
• Y is O, S(O).sub.n (n=0, 1 or 2), --O--CO--, --CO--O--, azo, carbonylamino, aminocarbonyl, aminocarbonyloxy, C.sub.1 -C.sub.8 -alkylene, C.sub.2 -C.sub.8 -alkenylene, C.sub.2 -C.sub.8 -alkynylene, C.sub.1 -C.sub.8 -alkylenoxy, oxy-C.sub.1 -C.sub.4 -alkylene, C.sub.1 -C.sub.8 -thioalkylene, oxycarbonyl-C.sub.1 -C.sub.8 -alkylene, carbonyloxy-C.sub.1 -C.sub.8 -alkylene, oxy-C.sub.2 -C.sub.8 -alkylenoxy, oxy-C.sub.2 -C.sub.8 -alkenylene, C.sub.1 -C.sub.8 -alkylamino, carbonyl-C.sub.1 -C.sub.8 -alkylamino, C.sub.1 -C.sub.8 -alkylaminocarbonyl, C.sub.1 -C.sub.8 -alkylaminocarbonyloxy, oxyimino or iminooxyalkylene,
• Z is C.sub.1 -C.sub.18 -alkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.10 -alkyl, C.sub.1 -C.sub.10 -haloalkyl, C.sub.2 -C.sub.18 -alkenyl, C.sub.3 -C.sub.8 -alkynyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, aryl, aryl-C.sub.1 -C.sub.10 -alkyl, aryl-C.sub.2 -C.sub.10 -alkenyl, aryloxy-C.sub.1 -C.sub.10 -alkyl or hetaryl,
• where the radicals Z may be unsubstituted or substituted by cyano, formyl, nitro, halogen, 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 -alkyl, C.sub.1 -C.sub.4 -dialkoxy-C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -haloalkenyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, unsubstituted or substituted C.sub.1 -C.sub.10 -alkoxyimino, C.sub.2 -C.sub.10 -alkenyloxyimino, aralkyloxyimino, unsubstituted or substituted C.sub.2 -C.sub.10 -alkanoyl, unsubstituted or substituted phenyl or phenoxy, or are an unsubstituted or substituted carbon-bonded 5-membered heterocyclic structure which contains from one to four identical or different heteroatoms selected from nitrogen, oxygen or sulfur, in which two adjacent substituents may form an unsubstituted or substituted aromatic or heteroaromatic ring.