Tetrahydrophthalamide derivative, intermediate for producing the

Details Tetrahydrophthalamide derivative, intermediate for producing the Tetrahydrophthalamide derivative, intermediate for producing the

1994-09-19

1996-04-09

Kumar, Shailendra

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

504220, 504235, 504249, 504266, 504287, 540607, 544176, 544391, 546226, 548200, 548539, 564191, A01N 4360, A01N 4378, C07D26530, C07C23365

Patent

active

055061907

DESCRIPTION:

BRIEF SUMMARY
This application is a 35 USC 371 of PCT/JP/93/00360 filed Mar. 25, 1993


TECHNICAL FIELD

In recent years, chemical agricultural agents have been essential materials for modern agriculture, and, as social demands for these chemical agricultural agents including herbicides, agents having low toxicity and residue and high selectivity to crops are desired. The present invention is to provide novel herbicides which meet the above-described social demands.
More specifically, the present invention relates to a 3,4,5,6-tetrahydrophthalamide derivative represented by the general formula (I): ##STR2## wherein X.sup.1 represents a halogen atom, X.sup.2 represents a hydrogen atom or a halogen atom, R.sup.1 represents a cycloalkyl group having from 3 to 8 carbon atoms which may be substituted, R.sup.2 represents a hydrogen atom, a chlorine atom or a methyl group, R.sup.3 and R.sup.4 each independently represents a hydrogen atom, an alkyl group having from 1 to 12 carbon atoms, a cycloalkyl group having from 3 to 9 carbon atoms, an aryl group having from 6 to 10 carbon atoms, an alkenyl group having from 3 to 5 carbon atoms or an alkynyl group having from 3 to 5 carbon atoms, or R.sup.3 and R.sup.4 may form, together with the nitrogen atom to which they are attached, a substituted or unsubstituted alicyclic heterocyclic ring; a process for preparing the same; and a herbicide containing the same as an active ingredient.
Further, the present invention relates to a 3,4,5,6-tetrahydroisophthalimide derivative represented by the general formula (V): ##STR3## wherein X.sup.1 represents a halogen atom, X.sup.2 represents a hydrogen atom or a halogen atom, R.sup.1 represents a cycloalkyl group having from 3 to 8 carbon atoms which may be substituted, A-B represents NH--C(OH) or N.dbd.C, and R.sup.2 represents a hydrogen atom, a chlorine atom or a methyl group; a process for preparing the same; and a herbicide containing the same as an active ingredient.
Also, the 3,4,5,6-tetrahydroisophthalimide derivatives represented by the general formula (V) per se are useful as active ingredients of the herbicide, and also, for example, 3,4,5,6-tetrahydrophthalimideohydroxy derivatives represented by the general formula (V) wherein A-B represents NH--C(OH) can be easily converted by dehydration reaction under heating into the 3,4,5,6tetrahydrophthalimide derivatives represented by the general formula (II) which are useful as active ingredients for the herbicides disclosed in Japanese Patent Publication (Kokai) No. 4-164067. (Refer to Reference Example 19 below.) ##STR4##
Furthermore, the 3,4,5,6-tetrahydroisophthalimide derivatives represented by the general formula (IV) can be easily converted by reacting with various amines into the 3,4,5,6-tetrahydrophthalamide derivatives represented by the general formula (I) which are the compounds of the present invention and are useful as active ingredients as herbicides.


TECHNICAL BACKGROUND

Hithertofore, as 3,4,5,6-tetrahydrophthalimide derivatives having an herbicidal activity, for example, Japanese Patent Publication (Kokai) Nos. 54-154737, 55-157546 (Japanese Patent Publication No. 63-13981), 59-51250, 60-252457, 61-43160, or U.S. Pat. No. 4,613,675 have been known, but the compounds having a cycloalkyloxy group at the 5-position of the phenyl ring on the nitrogen atom thereof have not been known.
Also, it is conventionally known that the 3,4,5,6-tetrahydrophthalamic derivatives having a carboxylic acid residual group and an amido group which are synthesized by reacting an aniline derivative with 3,4,5,6-tetrahydrophthalic anhydride (for example, the compounds disclosed in Japanese Patent Publication (Kokai) Nos. 48-44425, 54-125640 and 59-67255) exhibit a herbicidal activity, but the 3,4,5,6-tetrahydroisophthalimide hydroxy derivatives represented by the structure of the general formula (V') having a cycloalkyloxy group at the 5-position of the phenyl ring on the nitrogen atom thereof have not been known.
Further, as 3,4,5,6-tetrahydroisophthalimide derivatives, for example, the compound

REFERENCES:
patent: 3990880 (1976-11-01), Mumford
patent: 4328367 (1982-05-01), Nagase
patent: 5180587 (1993-01-01), Moore
patent: 5205853 (1993-04-01), Wolf et al.

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