Cyanooxime ethers, their preparation, agents containing them and their use

A cyanooxime ether of the formula I

• R.sup.1 R.sup.2 CH--OH.dbd.C(CN)--R.sup.3 I
• where
• R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl;
• R.sup.2 is a mononuclear to trinuclear aliphatic or aromatic ring system which is bonded via a carbon atom and, in addition to carbon atoms, may contain from one to four nitrogen atoms or from one to three hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, where this ring system may carry from one to five halogen atoms and/or from one to four of the following radicals:
• cyano, cyanato, thiocyanato, nitro, amino, hydroxyl, carboxyl, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.15 -alkenyl, C.sub.3 -C.sub.15 -alkenyloxy, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.5 -C.sub.8 -cycloalkenyl, C.sub.3 -C.sub.8 -cycloalkoxy, C.sub.5 -C.sub.8 -cycloalkenyloxy, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylcarbonyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylcarboxyl,
• phenyl, phenoxy, phenylthio, phenylamino, phenyl-C.sub.1 -C.sub.4 -alkyl, phenoxy-C.sub.1 -C.sub.4 -alkyl, phenylthio-C.sub.1 -C.sub.4 -alkyl or phenylamino-C.sub.1 -C.sub.4 -alkyl, where the aromatic rings in turn may carry from one to five halogen atoms and from one to three of the following radicals:
• cyano, nitro, 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 and C.sub.1 -C.sub.4 -haloalkylthio, or where the aromatic rings in turn may carry from one to five halogen atoms or from one to three of the following radicals:
• cyano, nitro, 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 and C.sub.1 -C.sub.4 -haloalkylthio;
• a five-membered or six-membered aromatic ring system which is bonded via a carbon atom and, in addition to carbon atoms, may contain from one to three nitrogen atoms or one or two nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom, where this ring system may carry from one to four halogen atoms and from one to three of the following radicals=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 and C.sub.1 -C.sub.4 -haloalkylthio, or where the aromatic rings in turn may carry from one to four halogen atoms or from one to three of the following radicals:
• 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 and C.sub.1 -C.sub.4 -haloalkylthio;
• or where this ring system may carry from one to five halogen atoms or from one to four of the following radicals:
• cyano, cyanato, thiocyanato, nitro, amino, hydroxyl, carboxyl, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.15 -alkenyl, C.sub.3 -C.sub.15 -alkenyloxy, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.5 -C.sub.8 -cycloalkenyl, C.sub.3 -C.sub.8 -cycloalkoxy, C.sub.5 -C.sub.8 -cycloalkenyloxy, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 C.sub..sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylcarbonyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.1 -C.sub.6 -alkylcarboxyl,
• phenyl, phenoxy, phenylthio, phenylamino, phenyl-C.sub.1 -C.sub.4 -alkyl, phenoxy-C.sub.1 -C.sub.4 -alkyl, phenylthio-C.sub.1 -C.sub.4 -alkyl or phenylamino-C.sub.1 -C.sub.4 -alkyl, where the aromatic rings in turn may carry from one to five halogen atoms and from one to three of the following radicals:
• cyano, nitro, 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 and C.sub.1 -C.sub.4 -haloalkylthio, or where the aromatic rings in turn may carry from one to five halogen atoms or from one to three of the following radicals:
• cyano, nitro, 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 and C.sub.1 -C.sub.4 -haloalkylthio;
• a five-membered or six-membered aromatic ring system which is bonded via a carbon atom and, in addition to carbon atoms, may contain from one to three nitrogen atoms or one or two nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom, where this ring system may carry from one to four halogen atoms and from one to three of the following radicals:
• 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 and C.sub.1 -C.sub.4 -haloalkylthio, or where the aromatic rings in turn may carry from one to four halogen atoms or from one to three of the following radicals:
• 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 and C.sub.1 -C.sub.4 -haloalkylthio, and
• R.sup.3 is unsubstituted or substituted alkyl or an unsubstituted or substituted aliphatic ring system which is bonded via a carbon atom and, in addition to carbon atoms, may contain one or two hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen.