Plant protecting and regulating compositions – Plant growth regulating compositions – Plural active ingredients
Patent
1994-07-20
1996-04-23
Dees, Jose G.
Plant protecting and regulating compositions
Plant growth regulating compositions
Plural active ingredients
560 43, 562433, 562457, A01N 2700, A01N 2904, A01N 2910, C07C22936
Patent
active
055103170
DESCRIPTION:
BRIEF SUMMARY
TECHNOLOGICAL FIELD!
The present invention relates to herbicides, and more particularly to N-acyl-N-phenylmaleamic 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-phenylmaleamic 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 maleamic acid derivatives has not been reported in large numbers.
It is an object of the present invention to provide N-acyl-N-phenylmateamic 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 maleamic acid derivatives each having a specific substituent acyl group or substituent aryl 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-acyl-N-phenylmaleamic 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 alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxyalkyl group or a lower alkoxycarbonylalkyl group, R.sup.2 represents a lower alkyl group, a halogenated lower alkyl group or a substituted or unsubstituted phenyl group, R.sup.3 represents a hydrogen atom or a lower alkyl group, and R.sup.4 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.
N-acyl-N-phenylmaleamic acid derivatives I! as compounds of the present invention can be synthesized, for example, by the following methods.
SYNTHESIS METHOD (a)!
N-acyl-N-phenylmaleamic acid derivatives I! which are compounds of the present invention can be synthesized by reacting imidoylchloride derivatives represented by the general formula II! with carboxylic acids represented by the general formula III!, without using any solvent or in a suitable solvent such as benzene, toluene, xylene, methylene chloride, chloroform, ethyl acetate, dioxane, tetrahydrofuran, diethylether, N,N-dimethylformamide or dimethyl sulfoxide, with the addition of a suitable deacidifying agent such as an organic base such as triethylamine or pyridine or an inorganic base such as potassium hydroxide or sodium hydroxide.
The reaction temperature is usually from -20.degree. C. to 250.degree. C. and preferably from 0.degree. C. to 100.degree. C. ##STR3## wherein X and Y each individually represent hydrogen atoms or halogen atoms, R.sup.1 represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxyalkyl group or a lower alkoxycarbonylalkyl group, R.sup.2 represents a lower alkyl group, a halogenated lower alkyl group or a substituted or unsubstituted phenyl group, R.sup.3 represents a hydrogen atom or a lower alkyl group, and R.sup.4 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.
SYNTHESIS METHOD (b)!
N-acyl-N-phenylmaleamic acid derivatives I! which are compounds of the present invention can be synthesized by reacting imidoylchloride derivatives represented by the general formula II! with alkali metal salts III'! of carboxylic acids represented by the general formula III!, without using any solvent or in a suitable
Ikeda Yukio
Kawamura Matsue
Komata Takeo
Kume Takashi
Mori Kaoru
Central Glass Co. Ltd.
Conrad, III Joseph M.
Dees Jos,e G.
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