Cyclohexenone oxide ethers and use thereof as herbicides

Details Cyclohexenone oxide ethers and use thereof as herbicides Cyclohexenone oxide ethers and use thereof as herbicides

1994-08-11

1996-03-05

Haley, Jacqueline

Plant protecting and regulating compositions

Seed coated with agricultural chemicals other than fertilizers

504271, 504280, 504288, 504289, 504292, 504294, 504343, 548235, 548247, 5483731, 5483771, 549 13, 549 75, 549426, 549491, 546254, 564256, A01N 4356, C07D23112

Patent

active

054967929

DESCRIPTION:

BRIEF SUMMARY
This application is a National Stage Application of PCT/EP93/0021 5 filed 30 Jan. 1993, now W093/16063, published 19 Aug. 1993.
The present invention relates to novel cyclohexenone oxime ethers of the general formula I ##STR2## where: R.sup.1 is C.sub.1 -C.sub.6 -alkyl; -C.sub.3 -alkyl; -haloalkyl; 5 if all the Xs are halogen; -C.sub.4 -alkylthio-C.sub.1 -C.sub.6 -alkyl; C.sub.3 -C.sub.7 -cycloalkyl or C.sub.5 -C.sub.7 -cycloalkenyl, it being possible if desired for these groups to carry one to three substituents selected from a group consisting of C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, hydroxyl and halogen; a 5-membered saturated heterocycle which consists of one or two oxygen and/or sulfur atoms as hetero atoms and which can, if desired, additionally carry one to three substituents selected from a group consisting of C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio and C.sub.1 -C.sub.4 -haloalkyl; a 6- or 7-membered heterocycle having one or two non-adjacent oxygen and/or sulfur atoms as hetero atoms which can be saturated or mono- or diunsaturated, it being possible if desired for the heterocycle additionally to carry one to three substituents selected from a group consisting of hydroxyl, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio and C.sub.1 -C.sub.4 -haloalkyl, a 5-membered heteroaromatic, containing one or two nitrogen atoms and an oxygen or sulfur atom, it being possible for this ring if desired additionally to carry one to three substituents selected from a group consisting of halogen, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkenyloxy and C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl; phenyl or pyridyl, it being possible for these groups if desired additionally to carry one to three of the following substituents selected from a group consisting of halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyloxy and an amino group --NR.sup.a R.sup.b, where C.sub.3 -C.sub.6 - alkynyl and C.sub.3 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -acyl or benzoyl which if desired can in turn additionally carry one to three radicals selected from a group consisting of nitro, cyano, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio and C.sub.1 -C.sub.4 -haloalkyl; and the agriculturally utilizable salts and esters of C.sub.1 -C.sub.10 -carboxylic acids and inorganic acids of the compounds I.
The invention additionally relates to a process for-preparing these compounds, their use as herbicides and herbicidal agents which contain these compounds as active substances.
In addition, the invention relates to novel hydroxylamines of the formula III ##STR3## where W is a C.sub.2 -C.sub.4 -alkylene chain which, if desired, is substituted by C.sub.1 -C.sub.3 -alkyl; -haloalkyl and 5 if all the Xs are halogen.
Herbicidally active cyclohexanediones of the formula I' ##STR4## are already known from the literature, where R.sup.c, R.sup.d and R.sup.e have, inter alia, the following meanings: =2-ethylthiopropyl); but-2-enyl; R.sup.e =a substituted 5-membered heteroaryl radical); R.sup.e =substituted phenyl); 4-phenylbutylene or 4-phenylbutenylene radical; R.sup.e =a substituted 5- to 7-membered heterocycle); 3-phenoxypropylene or 2-phenoxyethylene radical; R.sup.e =a substituted 5- to 7-membered heterocycle).
The herbicidal properties of these compounds, in particular with respect to their selectivity for weeds in graminaceous crop plants, however, may only give limited satisfaction.
Hence, it was an object of the present invention to provide novel cyclohexenone oxime ethers having improved selectivity for weeds in graminaceous crops such as rice and maize.
We have found that this object is achieved by the c

REFERENCES:
patent: 4440566 (1984-04-01), Luo
patent: 5190573 (1993-03-01), Misslitz et al.

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