Patent EA-001679-B1 (EA)
Title: Cyclohexenine oxime ether metal salts
Inventor: BRATZ MTTHIAS
IPC: C07C323/47
Filed: 1996-11-28
Abstract: 1. A cyclohexenone oxime ether metal salt of the formula I   where the variables have the following meanings:  R<a> is C1-C6-alkyl; R<b> is the equivalent of an alkali metal, alkaline earth metal or transition metal; R<c> is hydrogen, cyano, formyl, C1-C6-alkyl, C1-C4-alkoxy- C1-C6-alkyl, C1-C4-alkylthio- C1-C6-alkyl, phenoxy- C1-C6-alkyl, phenylthio- C1-C6-alkyl, pyridyloxy- C1-C6-alkyl or pyridylthio- C1-C6-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, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C3-C6-alkenyl, C3-C6-alkenyloxy, C3-C6-alkynyl, C3-C6-alkynyloxy and -NR<g>R<h>, where  R<g> is hydrogen C1-C4-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-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, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-alkythio [sic] and R<h> is hydrogen C1-C4-alkyl, C3-C6-alkenyl or C3-C6-alkynyl; C3-C7-cycloalkyl group or a C5-C7-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, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkylthio, benzylthio, C1-C4-alkylsulfonyl and C1-C4-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 C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-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, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-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, o~ 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, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C2-C6-alkenyl, C2-C6-alkenyloxy, C3-C6-alkynyloxy and C1-C4-alkoxy- C1-C4-alkyl; phenyl- [sic] 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, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C3-C6-alkenyl, C3-C6-alkenyloxy, C3-C6-alkynyl, C3-C6-alkynyloxy and -NR<k>R<1>, where  R<k> is hydrogen, C1-C4-alkyl, C3-C6-alkenyl or C3-C6-alkynyl and  R<1> is hydrogen, C1-C4-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-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, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-alkylthio; R<d> is hydrogen, hydroxyl or, if R<c> is C1-C6-alkyl, also C1-C6-alkyl; R<e> is hydrogen, cyano, halogen, (C1-C4-alkoxy)carbonyl or (C1-C4-alkyl)ketoxime; Alk is a C1-C6-alkylene chain, C3-C6-alkenylene chain or C3-C6-alkynylene chain, each of which can have attached to it a methylene group (=CH2) and/or one to three substituents, in each case selected from the group consisting of halogen and C1-C3-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 C1-C3-alkyl substituents and which, in addition to methylene or methine units, contains one of the following bridge members: oxygen, sulfur, -SO-, -SO2-or -N(R<i>)-, where R<i> is hydrogen, C1-C4-alkyl, C3-C6-alkenyl or C3-C6-alkynyl; R<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, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-alkenyl, C3-C6-alkenyloxy, C3-C6-alkynyl, C3-C6-alkynyloxy and -NR<k>R<1>, where R<k> is hydrogen, C1-C4-alkyl, C3-C6-alkenyl or C3-C6-alkynyl and R<1> is hydrogen, C1-C4-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-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, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-alkylthio. 2. A cyclohexenone oxime ether metal salt of the formula I as claimed in claim 1, where R<b> is lithium ion; R<c> is a 6- or 7-membered saturated or mono- or diunsaturated 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 hydroxyl, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-alkylthio and  R<d> and R<e> are hydrogen. 3. A cyclohexenone oxime ether metal salt of the formula I as claimed in claim 1, where  R<a> is ethyl or n-propyl, R<b> is a lithium ion, sodium ion, potassium ion or the equivalent of a magnesium ion, R<c> is tetrahydropyran-3-yl, tetrahydropyran-4-yl or tetrahydrothiopyran-3-yl, R<d> and R<e> are in each case hydrogen and R<f> is halophenyl. 4. The use of the cyclohexenone oxime ether metal salt of the formula I as claimed in claims 1 to 3 as a herbicide. 5. A herbicidal composition comprising a herbicidally active amount of at least one cyclohexenone oxime ether metal salt of the formula I as claimed in claims 1 to 3 and at least one inert liquid and/or solid carrier and, if desired, at least one surfactant. 6. A process for the preparation of herbicidally active compositions, which comprises mixing a herbicidally active amount of at least one cyclohexenone oxime ether metal salt of the formula I as claimed in claim 1 and at least one inert liquid and/or solid carrier and, if desired, at least one surfactant. 7. A method of controlling undesirable vegetation, which comprises allowing a herbicidally active amount of at least one cyclohexenone oxime ether metal salt of the formula I as claimed in claim 1 to act on plants, their environment or on seed. 8. A process for the preparation of cyclohexenone oxime ether metal salts of the formula I as claimed in claim 1, which comprises reacting the corresponding free compounds of the formula II   where R<a>, R<c> to R<f> and Alk have the same meanings as in formula I, with a metal hydroxide, metal hydride, metal (C1-C5-aIkoxide) or lithium or magnesium carbonate.