Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1993-09-30
1995-07-25
Shah, Mukund J.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
544 97, 5142288, A01N 4386, C07D26506
Patent
active
054362245
DESCRIPTION:
BRIEF SUMMARY
This is a national stage application (37 CFR 1.371) of PCT/JP93/00105, filed Jan. 28, 1993.
TECHNICAL FIELD
This invention relates to novel 1,3-oxazin-4-one derivatives having a tertiary alkyl substituent at the 3-position thereof, method for preparing the same, use thereof as a herbicide, and novel intermediates for preparing the same.
BACKGROUND ART
Certain types of 4H-2,3-dihydro-1,3-oxazin-4-one derivatives are described in, for example, Tetrahedron Lett., (33), 2905 (1976), Heterocycles, 17, 298 (1982), Chem. Pharm. Bull., 35(5), 1871 (1987), etc. and thus they are known.
However, the compounds described in the abovementioned publications differ from the compounds of this invention since none of them has a tertiary alkyl substituent on the 3-position of a 1,3-oxazine ring and no mention is made of their herbicidal activity and plant growth control activity.
U.S. Pat. Nos. 5,006,157 and 5,076,834 disclose 1-(1-methyl-1-phenylethyl)-3-phenyl-1,2,5,6-tetrahydropyridin-2-one derivatives and their use as a herbicide.
DISCLOSURE OF INVENTION
According to this invention, there are provided 1,3-oxazin-4-one derivatives represented by general formula (I) which follows ##STR2## wherein R.sup.1 is a lower alkyl group, a lower alkenyl group, an aryl group which may be substituted, or an aralkyl group which may be substituted;
R.sup.2 is a hydrogen atom or a lower alkyl group;
R.sup.3 is a lower alkyl group, an aryl group which may be substituted, or an aralkyl group which may be substituted; and
R.sup.4 and R.sup.5, independently each is a lower alkyl group , or R.sup.4 and R.sup.5, taken together with the carbon atom to which they are bonded, combine to form a 3- to 8-membered carbocyclic group which may have, as a substituent, a lower alkyl group.
The compounds of general formula (I) above provided by this invention have remarkable selective herbicidal activity, give no phytotoxicity to useful crops, and exhibit excellent herbicidal activity to various weeds at a very low dose, and therefore they are useful as herbicides.
BEST MODE FOR CARRYING OUT THE INVENTION
In the description and claims, the term "lower" means that groups or compounds to which this term is attached have 6 or less carbon atoms, preferably 4 or less carbon atoms.
"Lower alkyl group" may be either straight chained or branched chained, and includes, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, etc. groups.
"Lower alkenyl group" may be either straight chained or branched chained, and includes, for example, allyl, 2-methyl-2-propenyl, 2-butenyl, 3-butenyl, 3-methyl-2-butenyl, etc., groups.
"Lower alkynyl group" may be either straight chained or branched chained, and includes, for example, 2-propynyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl, etc., groups.
"Halogen atom" includes four species, i.e., fluorine atom, chlorine atom, bromine and iodine atom.
"Lower alkoxy group" means lower alkyl-O-group of which the lower alkyl moiety has the above-described meaning, and includes, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, etc., groups.
"Lower haloalkyl group" means one of which at least one hydrogen atom is substituted by a halogen atom, and includes, for example, trifluoromethoxy, difluoromethoxy, chlorodifluoromethoxy, 2-chloroethoxy, 1,1,2,2-tetrafluoroethoxy, 3-chloropropoxy, 2,2,3,3,3-pentafluoropropoxy, etc., groups.
"Aryl group" may be either monocyclic or polycyclic, and specific examples thereof include phenyl, naphthyl, etc., groups. Substituent group(s) on the ring of the "aryl group which may be substituted" may include halogen atoms, lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, a nitro group, etc. The aryl group may be substituted with at least one, preferably 1 to 4, and more preferably 1 to 3, of the substituent groups. Specific examples of such a substituted group include 2-fluorophenyl, 4-chloro-2-naphthyl, 2-to
REFERENCES:
patent: 2582128 (1952-01-01), Hurwitz
patent: 5006157 (1991-04-01), Ohba et al.
patent: 5076834 (1991-12-01), Ohba et al.
CA 119:219601, Osabe et al., (1993).
CA 117:90305, Goto et al., (1992).
Maujean et al., Tetrahedron Letters, No. 33, pp. 2905-2908 (1976).
Sato et al., Heterocycles, vol. 17, (1982), pp. 297-300.
Yamamoto et al., Chem. Pharm. Bull., vol. 35(5) pp. 1860-1879 (1987).
Sato et al., Chem. Pharm. Bull., vol. 31(6) pp. 1896-1909 (1983).
Sato et al., Chem. Pharm. Bull., vol. 32(7) pp. 2602-2608 (1984).
Go Atsushi
Hamatani Takeshi
Hasebe Hirokazu
Hayashizaki Keiichi
Hikido Mitsuru
Daicel Chemical Industries Ltd.
Grumbling Matthew V.
Mitsubishi Petrochemical Co. Ltd.
Shah Mukund J.
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