Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1994-08-11
1997-04-08
Bernhardt, Emily
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
504250, 504251, 504252, 504253, 504256, 504267, 504270, 504271, 504280, 504288, 504289, 504290, 504291, 504292, 504293, 504294, 504295, 504315, 504344, 544354, 546261, 5462801, 5462804, 5462817, 5462821, 5462834, 5462837, 5462721, 5462754, 546300, 548170, 548221, 548243, 548247, 5483661, 5483664, 5483731, 549 9, 549 13, 549 28, 549426, 549416, 549417, 549346, 560 16, 560 35, 564256, 564348, A01N 4360, A01N 4316, C07D24144, C07D30906
Patent
active
056187750
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP93/00210, filed Jan. 30, 1993.
The present invention relates to novel mixtures of optically active cyclohexenone oxime ethers having the R- and S-configuration in the oxime ether moiety and of the general formula I ##STR3## where
R.sup.1 is C.sub.1 -C.sub.6 -alkyl;
Z is one of the following groups: ##STR4##
X is halogen or C.sub.1 -C.sub.4 -haloalkyl;
m is from 0 to 3, or from 1 to 4 where all X are halogen;
n is from 0 to 3, or from 1 to 5 where all X are halogen;
R.sup.2 is C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.6 -alkyl or C.sub.1 -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, where these groups may, if desired, carry from one to three substituents selected from the 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 heterocyclic structure which contains one or two oxygen and/or sulfur atoms as hetero atoms and may, if desired, furthermore carry from one to three substituents selected from the 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-membered or 7-membered saturated or mono- or di-unsaturated heterocyclic structure which contains one or two oxygen or sulfur atoms or one oxygen and one sulfur atom as hetero atoms and may, if desired, furthermore carry from one to three substituents selected from the 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 structure containing from one to three hetero atoms selected from the group consisting of one or two nitrogen atoms and one oxygen or sulfur atom, where the heteroaromatic structure may, if desired, furthermore carry from one to three substituents selected from the 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, where these aromatic structures may, if desired, furthermore carry from one to three substituents selected from the 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
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,
R.sup.b 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, in turn may furthermore carry from one to three radicals selected from the 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 useful salts and esters of the compounds I with C.sub.1 -C.sub.10 -carboxylic acids and inorganic acids.
The present invention furthermore relates to a process for the preparation of these compounds, their use as herbicides, and herbicides which contain these mixtures.
The present invention also relates to novel mixtures of optically active hydroxylamines having the R- and S-configuration of the formula III ##STR5## where
Z is one of the following groups: ##STR6## where
X is halogen or C.sub.1 -C.sub.4 -haloalkyl,
m is from 0 to 3, or from 1 to 4 where all X are halogen, and
n is from 0 to 3, or from 1 to 5 where all X are halogen.
The literature discloses herbicidal cyclohexanediones of the formula I' ##STR7## where R.sup.c, R.sup.d and R.sup.e have, inter alia, the following meanings:
U.S. Pat. No. 4,440,566 (R.sup.c is ethyl or propyl, R.sup.d is benzyl and R.sup.e is 2-ethylthiopropyl);
EP-A 238 021 and EP-A 125 094 (R.sup.c is
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Sumitomo Chemical Co. Chem. Abst., vol. 102, No. 19, May 13, 1985, Abstract No. 166459f, p. 591 (English abstract of JP-A 60/006645).
Go et al Chem. Abst., vol. 111, No. 17, Oct. 23, 1989, Abstract No. 153345b, p. 674 (English abstract of JP-A 63/230665).
Gerber Matthias
Kardorff Uwe
Kast Juergen
Ladner Wolfgang
Meyer Norbert
BASF - Aktiengesellschaft
Bernhardt Emily
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