N-acyl-n-phenyltetrahydrophthalamic acid derivatives, methods of

Details N-acyl-n-phenyltetrahydrophthalamic acid derivatives, methods of N-acyl-n-phenyltetrahydrophthalamic acid derivatives, methods of

1993-10-22

1995-11-21

Ford, John M.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

544105, A01N 4304, C07D26536

Patent

active

054687195

DESCRIPTION:

BRIEF SUMMARY
TECHNOLOGICAL FIELD

This invention relates to N-acyl-N-phenyltetrahydrophthalamic acid derivatives which are novel compounds, to methods of producing the same and to herbicides containing the same as the effective components, and to imidoylchloride derivatives as intermediate products and to methods of producing the same. N-acyl-N-phenyltetrahydrophthalamic acid derivatives of the present invention exhibit excellent herbicidal activity. The derivatives are useful as a herbicide which can be widely applied to upland, paddy field, orchard, pasture, turf, forest, non-crop land, etc. The derivatives are not harmful to crops.


BACKGROUND TECHNOLOGY

Hitherto, herbicidal activity of tetrahydrophthalamic acid derivatives has been well known. For example, N-(4'-chlorophenyl)-3, 4, 5, 6-tetrahydrophthalamic acid methyl ester is known, as is disclosed in JP-A (Patent) 48-44425.
However, the conventional tetrahydrophthalamic acid derivatives are not necessarily sufficient in herbicidal activity, or are substantially limited in herbicidal spectrum against weeds. Furthermore, these derivatives are insufficient in selectivity between crops and weeds, thereby inducing problems of safety for crops.
It is an object of the present invention to solve the aforementioned problems, and to provide novel compounds which are excellent in herbicidal activity but not harmful to crops, methods of producing the same and herbicides containing the same as the effective components, and intermediate products and methods of producing the same.


DISCLOSURE OF THE INVENTION

The inventors have found and already proposed that novel tetrahydrophthalamic acid derivatives each having a specific substituent acyl group bonded to an amide nitrogen atom are very excellent in herbicidal activity, selectivity and herbicidal spectrum (International Application PCT/JP91/01109). In view of this, the inventors have intensely studied, and as a result have completed the present invention.
The present invention provides N-acyl-N-phenyltetrahydrophthalamic acid derivatives represented by the general formula [I], methods of producing the same, and herbicides containing the same as the effective components: ##STR2## wherein R.sup.1 represents an alkyl group, an alkenyl group, an alkynyl group, an alkoxyalkyl group, a haloalkyl group, a haloalkenyl group, a haloalkynyl group or a cyanoalkyl group, R.sup.2 represents a lower alkyl group or a halogenated lower alkyl group, and R.sup.3 represents a lower alkoxy group, a lower alkenyloxy group, a lower alkynyloxy group, a lower alkoxyalkoxy group, a substituted or unsubstituted benzyloxy group, a lower haloalkyloxy group or a lower alkoxycarbonylalkoxy group.
Furthermore, the present invention provides imidoylchloride derivatives represented by the general formula [II] and methods of producing the same: ##STR3## wherein R.sup.1 represents an alkyl group, an alkenyl group, an alkynyl group, an alkoxyalkyl group, a haloalkyl group, a haloalkenyl group, a haloalkynyl group or a cyanoalkyl group, R.sup.2 represents a lower alkyl group or a halogenated lower alkyl group.
N-acyl-N-phenyltetrahydrophthalamic acid derivatives [I] of the present invention can be produced, for example, as is shown by the following formula, by reacting imidoylchloride derivatives represented by the general formula [II] with carboxylic acids represented by the general formula [III]. ##STR4## wherein R.sup.1 represents an alkyl group, an alkenyl group, an alkynyl group, an alkoxyalkyl group, a haloalkyl group, a haloalkenyl group, a haloalkynyl group or a cyanoalkyl group, R.sup.2 represents a lower alkyl group or a halogenated lower alkyl group, and R.sup.3 represents a lower alkoxy group, a lower alkenyloxy group, a lower alkynyloxy group, a lower alkoxyalkoxy group, a substituted or unsubstituted benzyloxy group, a lower haloalkyloxy group or a lower alkoxycarbonylalkoxy group.
The reaction can proceeds preferably in a suitable solvent such as benzene, toluene, xylene, methylene chloride, chloroform, ethyl acetate, dioxane, tetrahydrofuran

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