Mitsubishi Chemical Industries Limited

Kuni Matsuya

Seiichi Suzuki

Tetsuo Jikihara

Hiroki Ohta

Osamu Wakabayashi

Hiroshi Kasugai

Kazuo Matsui

Hiroyasu Aizawa

N-substituted-3,4,5,6-tetrahydrophthalimides in which the N-substituted group is a phenyl group having a substituted-oxy group at 3-position and a chlorine or bromine atom at 4-position and chlorine or hydrogen atom at 2-position have excellent herbicidal effect and are used as selective herbicides in a plant culturing.

N-Substituted tetrahydrophthalimide and herbicidal composition

Disclosed is a novel 1,2-alkylene-4-substituted urazole derivative which has unique biological activities, especially a herbicidal or weeding activity.

1,2-Alkylene-4-substituted urazole herbicides

A.DELTA..sup.1 - tetrahydrophthalic anhydride is reacted with an amine in the presence of lower fatty acid. Alternatively N-(4-hydroxyphenyl)-.DELTA..sup.1 -tetrahydrophthalimide or a salt thereof is reacted with an aralkyl halide. A N-substituted-.DELTA..sup.1 -tetrahydrophthalimide compound having herbicidal activity is produced. This compound has the formula ##EQU1## wherein R' is naphthyl; phenyl; phenyl substituted by 1-3 substituents selected from the group consisting of halogen, nitro, cyano, thiocyano, carboxyl, haloalkyl, lower alkyl and alkylthio; --CH.sub.2 Y wherein Y is phenyl, naphthyl or phenyl substituted by 1-5 substituents selected from the group consisting of halogen, nitro, lower alkyl and lower alkoxyl; or ##SPC1## Wherein Z is phenyl, naphthyl, or phenyl substituted by at least one substituent selected from the group consisting of halogen, nitro, lower alkyl and lower alkoxyl.

Herbicidal N-substituted-.DELTA..sup.1 -tetrahydrophthalimide

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Zama, Japan

Kuni Matsuya