Substituted cinnamic oxime and hydroxamide derivatives

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

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504166, 504168, 504219, 504243, 504286, 540601, 540529, 544 65, 544312, 548513, 558391, 560 17, 560 22, 560 32, 560 18, 560 35, 560135, 560136, 560358, 564256, 564265, A01N 4354, A01N 4350, C07D22310, C07D23526

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060136065

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BRIEF SUMMARY
The present invention relates to novel substituted cinnamic oxime derivatives of the formula I ##STR3## where the variables have the following meanings: R.sup.1 is halogen, nitro, cyano or trifluoromethyl; -haloalkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or hydroxy-C.sub.1 -C.sub.6 -alkyl; -C.sub.6 -haloalkyl, or R.sup.3 and R.sup.4 together are a chemical bond; possible for these groups to be unsubstituted or to carry one of the following radicals: hydroxyl, cyano, hydroxycarbonyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, (C.sub.1 -C.sub.6 -alkyl)carbonyl, (C.sub.1 -C.sub.6 -alkoxy)-carbonyl, (C.sub.1 -C.sub.6 -alkyl)carbonyloxy or a 3- to 7-membered azaheterocycle bonded to the nitrogen atom via a carbonyl bridge and which, in addition to carbon ring members, can also contain an oxygen or sulfur atom as a ring member; -C.sub.6 -alkynyl, phenyl or phenyl-C.sub.1 -C.sub.6 -alkyl, it being possible for the phenyl rings, if desired, to carry one to three substituents selected from the group consisting of cyano, nitro, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy and (C.sub.1 -C.sub.6 -alkoxy)carbonyl; -alkyl)carbonyl, (C.sub.1 -C.sub.6 -alkoxy)carbonyl; C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, hydroxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkylthio-C.sub.1 -C.sub.6 -alkyl, cyano-C.sub.1 -C.sub.6 -alkyl, (C.sub.1 -C.sub.6 -alkoxy)carbonyl-C.sub.1 -C.sub.6 -alkyl, (C.sub.1 -C.sub.6 -alkyl)carbonyl-C.sub.1 -C.sub.6 -alkyl, (C.sub.1 -C.sub.6 -alkyl)carbonyloxy-C.sub.1 -C.sub.6 -alkyl or phenyl-C.sub.1 -C.sub.6 -alkyl, it being possible for the phenyl ring, if desired, to carry one to three substituents selected from the group consisting of cyano, nitro, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy and (C.sub.1 -C.sub.6 -alkoxy) carbonyl; -C.sub.3 -alkylene chain which can carry a C.sub.1 -C.sub.6 -alkyl substituent; ##STR4## X.sup.1 and X.sup.2 independently of one another being oxygen or sulfur; R.sup.7 being hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl or amino and C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl or phenyl which, if desired, can carry one to three substituents selected from the group consisting of cyano, nitro, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy and (C.sub.1 -C.sub.6 -alkoxy)carbonyl;
The invention additionally relates to novel substituted cinnamic hydroxamide derivatives of the formula II ##STR5## where the variables R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.6, R.sup.7, R.sup.8, R.sup.9, X.sup.1 and X.sup.2 have the same meanings as in the compounds of the formula I and in which -haloalkyl, it being possible for the last two groups to carry one of the following radicals: hydroxyl, cyano, hydroxycarbonyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, (C.sub.1 -C.sub.6 -alkyl)carbonyl, (C.sub.1 -C.sub.6 -alkoxy)carbonyl, (C.sub.1 -C.sub.6 -alkyl)carbonyloxy or a 3- to 7-membered azaheterocycle bonded to the nitrogen atom via a carbonyl bridge and which, in addition to carbon ring members, can also contain an oxygen or sulfur atom as a ring member; -C.sub.6 -alkynyl, (C.sub.1 -C.sub.6 -alkyl)carbonyl, (C.sub.1 -C.sub.6 -haloalkyl)carbonyl, (C.sub.1 -C.sub.6 -alkoxy) carbonyl; phenyl rings, if desired, to carry one to three substituents selected from the group consisting of cyano, nitro, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy and (C.sub.1 -C.sub.6 -alkoxy)-carbonyl; and
In addition, the invention relates to and/or defoliation of plants, defoliation of plants, which contain the compounds I or II as active substances, the desiccation and/or defoliation of plants, and/or defoliation of plants using the compounds I or II, and also
EP-A-0 385 231 discloses that, inter alia, compounds of the formula IIIa ##STR6## where R.sup.a is hy

REFERENCES:
patent: 4979982 (1990-12-01), Brouwer et al.
patent: 4990174 (1991-02-01), Rueb et al.
patent: 5009701 (1991-04-01), Plath et al.
patent: 5017211 (1991-05-01), Wenger et al.
patent: 5035740 (1991-07-01), Poss
patent: 5045105 (1991-09-01), Grossmann et al.
patent: 5336663 (1994-08-01), Wenger et al.
Chem. Abst., vol. 105, No. 7, 1986, Abst. No. 60524v.

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