Mitsui Toatsu Chemicals, Incorporated

Keiichi Igarashi

Takeo Yoshimoto

Hideo Yamazaki

Hirohisa Yanagita

Yuji Enomoto

Mitsumasa Umemoto

Masaaki Ura

Yoshio Takasawa

Yutaka Kubota

Naoki Sato

Teruhiko Toyama

Kengo Oda

Yoshikata Hojo

Takeo Harayama

Osamu Morikawa

Yasunobu Funakoshi

Taisuke Kurechi

Tekeo Yoshimoto

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

Disclosed are novel 3-nitrobenzene sulfonanilide derivatives and, among others, that of the formula ##STR1## as well as fungicidal compositions containing such compounds as the active ingredient. The compounds of the invention are markedly effective in controlling plant diseases and, in particular, clubroot disease of Brassica spp., have no toxicity to men, beasts, and fishes, exert no phytotoxicity on crops, have neither irritant nor unpleasant odor, and manifest their excellent fungicidal effect at low concentrations. Accordingly, they are ideally useful in fungicidal compositions.

3-Nitrobenzene sulfonanilide derivatives and fungicidal compositions for

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

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

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

Musashino, Japan

Keiichi Igarashi