Patent ID: 6133202
Filing Date: 2000-10-17
Classification: A01N,C07C,C07D

Abstract:
A cyclohexenone oxime ether metal salt of the formula I ##STR7## where the variables have the following meanings: R.sup.a is C.sub.1 -C.sub.6 -alkyl;R.sup.b is a lithium ion or one equivalent of a magnesium ion;R.sup.c is hydrogen, cyano, formyl, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.6 -alkyl, a phenoxy-C.sub.1 -C.sub.6 -alkyl, phenylthio-C.sub.1 -C.sub.6 -alkyl, pyridyloxy-C.sub.1 -C.sub.6 -alkyl or pyridylthio-C.sub.1 -C.sub.6 -alkyl group, it being possible for the phenyl and pyridyl rings of these groups to have attached to them, if desired, one to three substituents, in each case selected from the group consisting of nitro, cyano, 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 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyl, C.sub.3 -C.sub.6 -alkynyloxy and --NR.sup.g R.sup.h, whereR.sup.g is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -acyl or benzoyl which, if desired, can have attached to it, in turn, a further one to three radicals, in each case selected from the group consisting of nitro, cyano, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy and C.sub.1 -C.sub.4 -alkythio andR.sup.h is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl;a C.sub.3 -C.sub.7 -cycloalkyl group or a C.sub.5 -C.sub.7 -cycloalkenyl group, it being possible for these groups, if desired, to have attached to them one to three substituents, in each case selected from the group consisting of hydroxyl, 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 -alkylthio, benzylthio, C.sub.1 -C.sub.4 -alkylsulfonyl and C.sub.1 -C.sub.4 -alkylsulfinyl;a 5-membered saturated heterocycle which, in addition to carbon atoms, contains one or two oxygen or sulfur atoms or one oxygen and one sulfur atom as ring members and which, if desired, can additionally have attached to it one to three substituents, in each case selected from the group consisting of C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy and C.sub.1 -C.sub.4 -alkylthio;a 6- or 7-membered saturated or mono- or diunsaturated heterocycle which, in addition to carbon atoms, additionally contains one or two oxygen or sulfur atoms or one oxygen and one sulfur atom as ring members and which, if desired, can additionally have attached to it one to three substituents, in each case selected from the group consisting of hydroxyl, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy and C.sub.1 -C.sub.4 -alkylthio;a 5-membered heteroaromatic ring which, in addition to carbon atoms, contains one or two nitrogen atoms and one oxygen or sulfur atom, or one to three nitrogen atoms, or one oxygen or one sulfur atom as ring members and which, if desired, can additionally have attached to it one to three substituents, in each case selected from the group consisting of cyano, 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 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyloxy and C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl;phenyl- or pyridyl, both of which can, if desired, have attached to them one to three substituents, in each case selected from the group consisting of nitro, cyano, formyl, 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 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyl, C.sub.3 -C.sub.6 -alkynyloxy and --NR.sup.k R.sup.l, whereR.sup.k is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl andR.sup.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -acyl or benzoyl which, if desired, can additionally have attached to it, in turn, one to three substituents, in each case selected from the group consisting of nitro, cyano, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy and C.sub.1 -C.sub.4 -alkylthio;R.sup.d is hydrogen, hydroxyl or, if R.sup.c is C.sub.1 -C.sub.6 -alkyl, also C.sub.1 -C.sub.6 -alkyl;R.sup.e is hydrogen, cyano, halogen, (C.sub.1 -C.sub.4 -alkoxy)carbonyl or (C.sub.1 -C.sub.4 -alkyl)ketoxime;Alk is a C.sub.1 -C.sub.6 -alkylene chain, C.sub.3 -C.sub.6 -alkenylene chain or C.sub.3 -C.sub.6 -alkynylene chain, each of which can have attached to it a methylene group (.dbd.CH.sub.2) and/or one to three substituents, in each case selected from the group consisting of halogen and C.sub.1 -C.sub.3 -alkyl;a 3- to 6-membered alkylene or 4- to 6-membered alkenylene chain which, if desired, can have attached to it one to three C.sub.1 -C.sub.3 -alkyl substituents and which, in addition to methylene or methine units, contains one of the following bridge members: oxygen, sulfur, --SO--, --SO.sub.2 -- or --N(R.sup.i)--, where R.sup.i is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl;R.sup.f is the phenyl group, a halophenyl or a dihalophenyl group, it being possible for each phenyl ring, if desired, to have attached to it one to three substituents, in each case selected from the group consisting of nitro, cyano, formyl, 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 -haloalkoxy, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyl, C.sub.3 -C.sub.6 -alkynyloxy and --NR.sup.k R.sup.l, whereR.sup.k is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl andR.sup.l is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -acyl or benzoyl which, if desired, can additionally have attached to it, in turn, one to three radicals, in each case selected from the group consisting of nitro, cyano, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy and C.sub.1 -C.sub.4 -alkylthio.