Mitsui Toatsu Chemicals, Incorporated

Takeo Yoshimoto

Keiichi Igarashi

Masaaki Ura

Yoshikata Hojo

Yuji Enomoto

Teruhiko Toyama

Hideo Yamazaki

Yoshio Takasawa

Hirohisa Yanagita

Naoki Sato

Mitsumasa Umemoto

Yutaka Kubota

Takeo Harayama

Yasunobu Funakoshi

Takashi Fujita

Kengo Oda

Osamu Morikawa

Akira Hosono

Joh Miki

Takayuki Inoue

Takao Baba

Hideo Michiyama

Hajime Tachibana

Taisuke Kurechi

Osamu Morikama

Disclosed herein are N-(2-chloro-4-nitrophenyl)-3-trifluoromethyl-benzenesulfonamide derivatives represented by the following general formula (I): ##STR1## wherein X and Y individually mean a hydrogen or chlorine atom and agricultural fungicides containing said derivatives.

N-(2-chloro-4-nitrophenyl)-3-trifluoromethyl-benzenesulfonamide

Disclosed herein are N-(2-chloro-4-nitrophenyl)-benzenesulfonamide derivatives represented by the following general formula (I): ##STR1## wherein X and Y individually mean a hydrogen or chlorine atom and Z denotes a chlorine atom or trifluoromethyl group, and agricultural fungicides containing said derivatives.

N-(2-chloro-4-nitrophenyl)-(benzenesulfonamide derivative and

Disclosed herein are N-(2-chloro-4-nitrophenyl)benzenesulfonamide derivatives represented by the following general formula (I): ##STR1## wherein X and Y individually mean a hydrogen or chlorine atom and Z denotes a chlorine atom or trifluoromethyl group, and agricultural fungicides containing said derivatives.

N-(2-Chloro-4-nitrophenyl)-benezene-sulfonamide derivative and

Disclosed herein are N-(2-chloro-4-trifluoromethylphenyl)-3-trifluoromethylbenzensulfonamide derivatives represented by the following general formula (I): ##STR1## wherein X and Y individually mean a hydrogen or chlorine atom, and agricultural fungicides containing said derivatives.

N-(2-chloro-4-trifluoromethylphenyl)-3-trifluoromethylbenzenesulfonamide

Novel diphenyl ether hydrazine derivatives, particularly 2-nitro-5 (nucleus-substituted phenoxy) phenylhydrazine derivatives are provided. They are useful as a selective herbicide having a high herbicidal activity and residual efficacy.

Diphenyl ether derivatives and herbicides containing same

Novel diphenyl ether hydrazine derivatives, particularly 2-nitro-5 (nucleus-substituted phenoxy) phenylhydrazine derivatives are provided. They are useful as a selective herbicide having a high herbicidal acitivity and residual efficacy.

3-nitro-4-methylbenzene sulfon-2-chloro-4-nitroanilide ##STR1## as a novel compound as well as fungicidal composition containing the compound as the active ingredient. The compound of the invention is markedly effective in controlling plant diseases and, in particular, clubroot disease of Brassica spp., has no toxicity to men, beasts, and fishes, exerts no phytotoxicity on crops, has neither irritant nor unpleasant odor, and manifests its excellent fungicidal effect at low concentrations. Accordingly, it is ideally useful in fungicidal composition.

3-Nitro-4-methylbenzene sulfon-2-chloro-4-nitroanilide and fungicidal

Novel diphenyl ether compounds of the general formula: ##STR1## wherein X represents a hydrogen atom or a nitro group, process for preparing the same and diphenyl ethers of the general formula: ##STR2## wherein R represents a hydrogen atom, or substituted or unsubstituted alkyl group, alkenyl group or alkynyl group, and Y represents an oxygen atom, a sulfur atom, or the group ##STR3## wherein R' is defined as R above by reacting 2-chloro-4-trifluoromethylphenyl-3,4-dinitrophenyl ether with a compound of the general formula:

Diphenyl ethers

Nitrodiphenyl ether derivatives of the general formula: ##STR1## wherein X represents chlorine, fluorine, methyl or trifluoromethyl and n is an integer of 1-3 are valuable as herbicides, the compounds and compositions containing these compounds possessing an excellent herbicidal activity to a wide variety of undesirable weeds with an extremely low toxicity to useful crops.

Herbicidal compounds and compositions

A tetrahydrofuran derivative represented by the general formula ##STR1## wherein X.sub.1 and X.sub.3 represent a hydrogen or halogen atom, and X.sub.2 represents a halogen atom or a trifluoromethyl group. The compounds have excellent herbicidal activity and can be prepared by reacting a compound of the formula ##STR2## wherein R represents a nitro group or a group of the formula ##STR3## in which X.sub.1, X.sub.2 and X.sub.3 are as defined above, with 3-hydroxytetrahydrofuran in the presence of an alkali.

Tetrahydrofuran derivatives

Novel diphenyl ether compounds of the general formula: ##STR1## wherein X represents a hydrogen atom or a nitro group, process for preparing the same and diphenyl ethers of the general formula: ##STR2## wherein R represents a hydrogen atom, or substituted or unsubstituted alkyl group, alkenyl group or alkynyl group, and Y represents an oxygen atom, a sulfur atom, or the group ##STR3## wherein R' is defined as R above, by reacting 2-chloro-4-trifluoromethylphenyl-3,4-dinitrophenyl ether with a compound of the general formula:

Process for preparing diphenyl ethers

Herbicidal diphenyl ether compound

Nitrodiphenyl ether derivatives of the general formula: ##STR1## wherein X stands for Cl, F, CH.sub.3 or CF.sub.3, n is an integer of 1-3 with the proviso that X may be the same or different when n is 2 or 3 but X.sub.n should not be 2,4-dichloro substituent, Are valuable as herbicides possessing an excellent herbicidal activity to a wide variety of undesirable weeds with an extremely low toxicity to useful crops. These nitrodiphenyl ether derivatives are prepared by hydroxyethylation of a compound of the above general formula except that a halogen atom is present in place of nitro group and subsequent halogenation of the .beta.-hydroxyethoxy group of the resulting compound.

Nitro-diphenyl ethers

2,4-Dichloro-3'-(.beta.-chloroethoxy)-4'-nitrodiphenyl ether is prepared by condensing 2,3',4-trichloro-4'-nitrodiphenyl ether with ethyleneglycol in the presence of an acid-binding agent and then chlorinating the hydroxyethoxy group of the resulting condensate. This compound posesses an excellent herbicidal activity to a wide variety of undesirable weeds with an extremely low phyto-toxicity to useful crops.

Growing community of inventors

Yokohama, Japan

Takeo Yoshimoto