N-aryloxyacyl-n-phenyltetrahydrophthalamic acid derivatives, met

Details N-aryloxyacyl-n-phenyltetrahydrophthalamic acid derivatives, met N-aryloxyacyl-n-phenyltetrahydrophthalamic acid derivatives, met

1994-07-19

1996-01-02

Dees, Jose G.

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

Organic compounds

Carboxylic acid esters

504315, 562455, C07C22938, A01N 3710

Patent

active

054810221

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/JP93/01756, filed Dec. 2, 1993.


TECHNOLOGICAL FIELD

This invention relates to herbicides, and more particularly to N-aryloxyacyl-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-aryloxyacyl-N-phenyl-tetrahydrophthalamic 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. Compounds disclosed in JP-A (Patent) 4-803407 are known as those solving these problems and exhibiting excellent herbicidal activity. However, there is no description about compounds having N-aryloxyacyl group in N-acyl group part nor about biological activity of these compounds.
It is an object of the present invention to solve the aforementioned conventional problems, and to provide N-aryloxyacyl-N-phenyltetrahydrophthalamic acid derivatives as novel compounds exhibiting excellent herbicidal activity against various very harmful weeds and not being 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 aryloxyacyl group bonded to an amide nitrogen atom are very excellent in herbicidal activity, selectivity and herbicidal spectrum, and completed the present invention.
The present invention provides N-aryloxyacyl-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 X and Y each individually represent hydrogen atoms or halogen atoms, Ar represents a substituted or unsubstituted phenyl group or naphthyl group, R.sup.1 represents a hydrogen atom, a halogen atom, a lower alkyl group, 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 hydrogen atom or a lower alkyl group, R.sup.3 represents a hydroxyl, a lower alkoxy group, a lower alkenyloxy group, a lower alkynyloxy group, a lower alkoxyalkoxy group, a benzyloxy group or a lower alkoxycarbonylalkoxy group, and m is an integer ranging from 0 to 5.
N-aryloxyacyl-N-phenyltetrahydrophthalamic acid derivatives [I] as compounds of the present invention can be synthesized, for example, by the following method.
Firstly, imidoylchloride derivatives represented by the general formula [III] are obtained as an intermediate product by reacting a dehydrochlorinating agent such as polymer-carried triphenylphosphine and carbon tetrachloride with anilide derivatives represented by the general formula [II] without using any solvent, or in a solvent such as methylene chloride, chloroform, benzene, toluene, xylene, ethyl acetate, ether, dioxane, tetrahydrofuran, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide or sulfolane, at a temperature ranging from 0.degree. C. to 200.degree. C. and preferably from 0.degree. C. to 100 .degree. C.
Then, a carboxylic acid represented by the general formula [IV] and a suitable deacidifying agent such as an organic base such as triethylamine or pyridine or an inorganic base such as po

REFERENCES:
patent: 4261730 (1981-04-01), Bollinger et al.
patent: 5068365 (1991-11-01), Tokunaga et al.
patent: 5292922 (1994-03-01), Takematsu et al.
patent: 5296454 (1994-03-01), Goto et al.
patent: 5334747 (1994-08-01), Steffen

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