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

1992-04-22

1994-03-08

Dees, Jose G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

560 45, 560 48, 504341, 504343, 564155, 564158, C07C22900, C07C23300

Patent

active

052929221

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. 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 is 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 a 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.


DISCLOSURE OF THE INVENTION

The inventors have found 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, and as a result have completed the present invention.
The present invention provides tetrahydrophthalamic acid derivatives represented by the general formula [I], methods of producing the same, and herbicides containing the same as the effective components: ##STR2## wherein X and Y each individually represent hydrogen atoms or halogen atoms, R.sup.1 represents a hydrogen atom, a halogen atom, a lower alkoxy group, a lower alkenyloxy group, a lower alkynyloxy group, a lower alkoxyalkoxy group or a lower alkoxycarbonylalkoxy group, R.sup.2 represents a lower alkyl group, a halogenated lower alkyl group or a substituted or unsubstituted phenyl group, and R.sup.3 represents a lower alkoxy group, a lower alkenyloxy group, a lower alkynyloxy group, a lower alkoxyalkoxy group, benzyloxy group or a lower alkoxycarbonylalkoxy group.
A compound of the invention can be synthesized, for example, by the following methods.


SYNTHESIS METHOD (a)

A compound of the invention which is represented by the general formula [I] can be synthesized by the reaction of imidoylchloride which is represented by the general formula [II] with a carboxylic acid which is represented by the general formula [III], in a suitable solvent such as benzene, toluene, xylene, methylene chloride, chloroform, ethyl acetate, dioxane, tetrahydrofuran, diethyl ether, dimethylformamide and dimethylsulfoxide, by adding a suitable deacidifying agent such as an organic base such as triethylamine and pyridine or an inorganic base such as potassium hydroxide and sodium hydroxide.
The reaction temperature is usually from 0.degree. C. to 200.degree. C., and a preferred range is from 40.degree. C. to 100.degree. C. ##STR3## wherein X, Y, R.sup.1, R.sup.2 and R.sup.3 are as defined hereinabove.


SYNTHESIS METHOD (b)

A compound of the invention which is represented by the general formula [I] can be synthesized by the reaction of imidoylchloride which is represented by the general formula [II] with an alkali metal salt of carboxylic acid which is represented by the general formula [IV], in a suitable solvent such as benzene, toluene, xylene, methylene chloride, chloroform, ethyl acetate, dioxane, tetrahydrofuran, diethyl ether, dimethylformamide and dimethylsulfoxide and water, by adding if necessary a phase transfer catalyst such as a quaternary ammonium salt.
The reaction temperature is usually from 0.degree. C. to 200.degree. C., and a preferred range

REFERENCES:
patent: 4324580 (1982-04-01), Vogel et al.
patent: 4465507 (1984-08-01), Konno et al.
Chang, "Preparation of N-substituted tetrahydrophthalimide herbicidal compounds . . . " PCT Int'l Application WO8704049, Jan. 10, 1986, CA 108(5):37640h, the Abstract only.

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