Sagami Chemical Research Center

Kaken Pharmaceutical Company, Ltd.

Chisso Corporation

Nippon Mining Co., Ltd.

Emiko Ejiri

Kenji Hirai

Tomoyuki Yano

Kiyomi Aizawa

Mitsuo Yamashita

Tomoko Tateno

Sadayuki Ugai

Yuichi Onji

Shoin Nagato

Osamu Yamada

Tomoko Yoshii

Kikuko Harasawa

Tomoko Matsukawa

Shigeki Kishi

Koichi Shikakura

Masakatsu Matsumoto

Tamotsu Fujimoto

Process for the production of aniline derivatives

The present invention relates to 3,4,5,6-tetrahydrophthalamide derivatives and 3,4,5,6-tetrahydroisophthalimide derivatives having excellent effects as effective active ingredients of herbicides, and processes for preparing the same, and provides the compounds having a more efficient herbicidal activity, and efficient and industrial processes for the preparation thereof. More specifically, the tetrahydrophthalimide derivative obtained by reacting a halogen-substituted 5-cycloalkyloxyaniline derivative with a 3,4,5,6-tetrahydrophthalic anhydride, or the tetrahydroisophthalimide derivative of the present invention is reacted with various types of amines to prepare a tetrahydrophthalamide derivative represented by the general formula (I): ##STR1## These tetrahydrophthalamide derivatives and the tetrahydroisophthalimide derivatives exhibit excellent herbicidal activities in the soil treatment in the paddy field and field and the stem-foliar treatment. The tetrahydroisophthalimide derivatives are also useful as intermediates for the preparation of the tetrahydrophthalamide derivatives, etc.

Tetrahydrophthalamide derivative, intermediate for producing the same,

A benzene derivative substituted with a heterocyclic ring represented by the general formula: ##STR1## wherein R represents a cycloalkyl group having 3 to 8 carbon atoms, X represents a halogen atom, and Z represents ##STR2## in which said cycloalkyl group may be substituted with an alkyl group having 1 to 6 carbon atoms, a process for preparing the same, and a herbicidal agent comprising the above compound as an active ingredient are disclosed. The compound has an excellent effect in that the compound exhibits a markedly high herbicidal effect on weeds in the field and the paddy field at a low dose and yet exhibits markedly low noxious effects on main crops.

Benzene derivatives substituted with heterocyclic ring and herbicides

Benzene derivatives substituted with heterocyclic ring, and herbicides

Disclosed are fluorobenzene derivatives, which are important intermediates for producing herbicidal oxazolidinedione derivatives, and methods of producing them. The fluorobenzene derivatives include compounds of a formula (11): ##STR1## where X is a halogen atom, R.sup.3 is a nitro, amino or isocyanato group or R.sup.1 OCONH, and R.sup.1 is an alkyl or phenyl group. Via the intermediates of the invention, oxazolidinedione derivatives can be produced with high yield.

Methods of preparing fluorobenzene derivatives and related compounds

Fluorobenzene derivatives

Bis(fluorophenyl) carbonate derivatives

Macrocyclic 2-halogenoketones are prepared by reacting a macrocyclic 2-hydroxyketone with a halogenating agent. This reaction may be carried out in the presence of a solvent and/or a catalyst.

Process for preparing macrocyclic 2-halogenoketones

Growing community of inventors

Kanagawa, Japan

Emiko Ejiri