1,3-oxazin-4-one derivatives as herbicides

Details 1,3-oxazin-4-one derivatives as herbicides 1,3-oxazin-4-one derivatives as herbicides

1998-09-02

2000-04-04

Shah, Mukund J.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

544 96, 544 97, C07D26506, C07D41306, C07D41706, C07D41304, A01N 4386

Patent

active

060461357

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP96/05404, filed on Dec. 4, 1996.
This invention relates to novel 1,3-oxazin-4-one derivatives, herbicidal compositions containing the same, and novel intermediates for preparing the same.
Certain types of 1,3-oxazin-4-one derivatives, such as 2,3-dihydro-6-methyl-3-(1-methyl-1-phenylethyl)-5-phenyl-4H-1,3-oxazin-4-o ne, and their herbicidal activities are disclosed in for example International Patent Publication No. WO 93/15064. However, the compounds described in the above-mentioned publication do not have a ketone or alcohol functionality in the group attached to the nitrogen atom at the 3-position of a 1,3-oxazine ring.
According to the present invention, there are provided 1,3-oxazin-4-one derivatives of formula I: ##STR2##
wherein:
R.sup.1 represents phenyl optionally substituted by from one to five groups which may be the same or different selected from halogen, hydroxy, lower alky, lower haloalkyl, lower alkoxy, lower haloalkoxy, --S(O).sub.n R.sup.7, --CO.sub.2 R.sup.7, --COR.sup.7, cyano, nitro, --O(CH.sub.2).sub.q CO.sub.2 R.sup.7 and phenoxy;
a five to seven membered heteroaromatic ring having from one to four ring heteroatoms which may be the same or different selected from nitrogen, oxygen and sulphur, said ring being optionally substituted by from one to four groups which may be the same or different selected from halogen, hydroxy, lower alkyl lower haloalkyl, lower alkoxy, lower haloalkoxy, --S(O).sub.n R.sup.7, --CO.sub.2 R.sup.7, --COR.sup.7, cyano, nitro, --O(CH.sub.2).sub.q CO.sub.2 R.sup.7 and phenoxy;
or a straight- or branched-chain optionally halogenated alkyl, alkenyl or alkynyl group containing up to ten carbon atoms;
R.sup.2 represents:
a hydrogen atom; or
a straight- or branched-chain alkyl group containing from one to ten carbon atoms which is optionally substituted by one or more groups R.sup.8 which may be the same or different;
a straight- or branched-chain optionally halogenated alkenyl or alkynyl group having up to ten carbon atoms;
or a group selected from cyano, --CHO, --COR.sup.7, --CO.sub.2 H, --CO.sub.2 R.sup.7, --COSR.sup.7, --CONR.sup.9 R.sup.10, --CH.dbd.NOH, --CH.dbd.NOR.sup.7, --CH.dbd.NOCOR.sup.7, --CH.dbd.NNR.sup.9 R.sup.10, --CH.sub.2 CN, --CH.sub.2 NO.sub.2 and oxiranyl;
R.sup.3 represents --(CH.sub.2).sub.r --(phenyl or naphthyl optionally substituted by from one to five groups which may be the same or different selected from halogen, hydroxy, lower alkyl lower haloalkyl lower alkoxy, lower haloalkoxy, --S(O).sub.n R.sup.6, --CO.sub.2 R.sup.6, --COR.sup.6, cyano, nitro, --O(CH.sub.2).sub.q CO.sub.2 R.sup.6, phenoxy and --SF.sub.5);
--(CH.sub.2).sub.s --five to seven membered heteroaromatic ring having from one to four ring heteroatoms which may be the same or different selected from nitrogen, oxygen and sulphur, said ring being optionally fused to a phenyl ring or to a second five to seven membered heteroaromatic ring having from one to four heteroatoms which may be the same or different selected from nitrogen, oxygen and sulphur, to form a bicyclic ring system, the monocyclic ring or either ring in the bicyclic system being optionally substituted by from one to four groups which may be the same or different selected from halogen, hydroxy, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, --S(O).sub.n R.sup.6, --CO.sub.2 R.sup.6, --COR.sup.6, cyano, nitro, --O(CH.sub.2).sub.q CO.sub.2 R.sup.6 and phenoxy);
a straight- or branched-chain optionally halogenated alkyl, alkenyl or alkynyl group containing up to ten carbon atoms;
a straight- or branched-chain optionally halogenated alkyl, alkenyl or alkynyl group containing up to ten carbon atoms which is substituted by cycloalkyl containing from three to six carbon atoms; or
cycloalkyl containing from three to six carbon atoms or cycloalkenyl containing five or six carbon atoms, the ring systems of which are optionally substituted by a group R.sup.6 or one or more halogen atoms which may be the same or different;
R.sup.4 and R.sup.5 independently represent lower alkyl

REFERENCES:
patent: 5436224 (1995-07-01), Hamatani et al.
patent: 5696054 (1997-12-01), Go et al.
Derwent Publications Ltd., abstract 92-147592/18 (abstract of JP 04-089485-A), 1992.

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