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

1998-04-13

2000-02-22

Raymond, Richard L.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

504130, 544 96, 544 97, A01N 4386, C07D26506

Patent

active

060280328

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

1. Field of the Invention
This invention relates to novel 1,3-oxazin-4-one derivatives, herbicidal compositions containing the same, and novel intermediates for preparing the same.
2. Description of the Related Art
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 Nos. WO 93/15064 and WO 95/10510.
However, the compounds described in the above-mentioned publications differ from the compounds of the present invention since none of them have an acid amide substituent in the group attached to the nitrogen atom of the 3-position of a 1,3-oxazin ring.


SUMMARY OF THE INVENTION

According to the present invention, there is provided a 1,3-oxazin-4-one derivative of the 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 alkyl, haloalkyl, alkoxy, 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 .sup.- CO.sub.2 R.sup.7 and phenoxy; which is substituted by one or more groups R.sup.8 which may be the same or different; group having up to ten carbon atoms; --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; which may be the same or different selected from halogen, hydroxy, lower alkyl, haloalkyl, alkoxy, haloalkoxy, --S(O).sub.n R.sup.7, --CO.sub.2 R.sup.7, --COR.sup.7 l cyano, nitro, --O(CH.sub.2).sub.q CO.sub.2 R.sup.7 and phenoxy; having from one to four ring heteroatoms which may be the same or different selected from nitrogen, oxygen and sulphur, said first 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 in which either ring is optionally substituted by from one to four groups which may be the same or different selected from halogen, hydroxy, lower alkyl, haloalkyl, alkoxy, 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, said first ring being linked to the nitrogen atom of the group NR.sup.6 via one of the ring carbon atoms; --COR.sup.7 or --CO.sub.2 R.sup.7 ; --OR.sup.7, --OCOR.sup.7, --S(O).sub.n R.sup.7 and --NR.sup.9 R.sup.10 ; haloalkyl; properties.
By the term "agriculturally acceptable salts" is meant salts the cations or anions of which are known and accepted in the art for the formation of salts for agricultural or horticultural use. Preferably the salts are water-soluble. Suitable salts with bases include alkali metal (eg. sodium and potassium), alkaline earth metal (eg. calcium and magnesium), ammonium and amine (eg. diethanolamine, triethanolamine, octylamine, morpholine and dioctylmethylamine) salts. Suitable acid addition salts, e.g. formed by compounds of formula (I) containing an amino group, include salts with inorganic acids, for example hydrochlorides, sulphates, phosphates and nitrates and salts with organic acids for example acetic acid.
In certain cases the groups R.sup.1, R.sup.2, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.9 and R.sup.10 may give rise to stereoisomers and geometric isomers. All such forms are embraced by the present invention.
In the description the following terms are generally defined thus: six carbon atoms. six carbon atoms, substituted by one or more halogens. carbon atoms. six carbon atoms, substituted by one or more halogens.
In the description that follows a number of preferred classes (because of their herbicidal properties) of compounds of formula (I) above are disclosed.
Compounds of formula (I) above in which R.sup.1 represents phenyl optionally substituted by one or mo

REFERENCES:
patent: 5436224 (1995-07-01), Hamatani et al.
patent: 5696054 (1997-12-01), Go et al.

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