Cyclohexenone oxime ethers, their preparation and their use

Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing

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504193, 504251, 504254, 504260, 504285, 504289, 504294, 504295, 504290, 504288, 504292, 504310, 504315, 504318, 504322, 504326, 504337, 504339, 504344, 546 14, 546200, 546283, 546284, 548110, 548247, 548405, 548517, C07D21304, C07D30904, A01N 4316, A01N 4318

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055146422

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BRIEF SUMMARY
This application is a 371 of PCT/EP93/02158 filed Aug. 13, 1993.
The present invention relates to cyclohexenone oxime ethers of the formula I ##STR2## in which the substituents have the following meanings:
R.sup.2 is C.sub.1 -C.sub.6 -alkyl;
R.sup.2 is C.sub.1 -C.sub.10 -alkyl, C.sub.1 -C.sub.10 -haloalkyl, C.sub.3 -C.sub.10 -alkenyl, C.sub.3 -C.sub.10 -haloalkenyl, C.sub.3 -C.sub.10 -alkynyl or C.sub.3 -C.sub.10 -haloalkynyl;
--A.sup.1 --O--N.dbd.CH--Ph or --A.sup.2 --W, where A.sup.1 is C.sub.2 -C.sub.4 -alkylene which may carry from one to three C.sub.1 -C.sub.3 -alkyl groups;
Ph is phenyl which may be unsubstituted or may carry from one to three radicals selected from a group consisting of nitro, cyano, halogen, C.sub.1 -C.sub.4 -alkyl and C.sub.1 -C.sub.4 -haloalkyl;
A.sup.2 is C.sub.1 -C.sub.6 -alkylene, C.sub.3 -C.sub.6 -alkenylene or C.sub.3 -C.sub.6 -alkynylene, where these radicals may in each case carry from one to three of the following groups: halogen and/or C.sub.1 -C.sub.3 -alkyl;
or is C.sub.2 -C.sub.5 -alkyleneoxy, C.sub.2 -C.sub.5 -alkenyleneoxy or C.sub.2 -C.sub.4 -alkyleneoxy-C.sub.1 -C.sub.3 -alkylene having a total of from three to five carbon atoms, where these radicals may in each case carry from one to three C.sub.1 -C.sub.3 -alkyl groups;
W is phenyl, pyridyl or thienyl, where the rings may in each case be unsubstituted or may carry from one to three of the following radicals: nitro, cyano, halogen, C.sub.1 -C.sub.4 -alkyl and/or C.sub.1 -C.sub.4 -haloalkyl;
R.sup.3 is C.sub.1 -C.sub.6 -alkyl which carries one of the following groups: C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio;
C.sub.3 -C.sub.7 -cycloalkyl or C.sub.5 -C.sub.7 -cycloalkenyl, where these radicals may be unsubstituted or may carry from one to three of the following substituents: hydroxyl, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy and/or C.sub.1 -C.sub.4 -alkylthio;
a 5-membered, saturated heterocyclic structure which, in addition to carbon ring members, may contain one or two oxygen and/or sulfur atoms, where this ring may be unsubstituted or may carry from one 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 and/or C.sub.1 -C.sub.4 -alkylthio;
a 6-membered or 7-membered, saturated or mono- or di-unsaturated heterocyclic structure which, in addition to carbon ring members, may contain one or two oxygen and/or sulfur atoms, where this ring may be unsubstituted or may carry from one to three of the following substituents: hydroxyl, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy and/or C.sub.1 -C.sub.4 -alkylthio;
a 5-membered heteroaromatic structure which, in addition to carbon ring members, contains one or two nitrogen atoms and one oxygen or one sulfur atom, where this ring may be unsubstituted or may carry from one to three of the following substituents: 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 -alkylthio, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl and/or C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl;
phenyl or pyridyl, where these rings may be unsubstituted or may carry from one to three of the following substituents: 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 -alkylthio, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyloxy and/or NR.sup.a R.sup.b, where
R.sup.a is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl, and R.sup.b is one of the radicals R.sup.a or is C.sub.1 -C.sub.6 -alkylcarbonyl or benzoyl, where the phenyl ring in turn may carry from one to three of the following radicals: 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/or C.sub.1 -C.sub.4 -alkylthio;
R.sup.4 is hydrogen;
C.sub.1 -C.sub.10 -alkyl, C.sub.1 -C.sub.10 -haloalkyl, C.sub.3 -C.sub.10 -alkenyl, C.sub.3 -C.sub.

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