Ishihara Sangyo Kaisha, Ltd.

Kanichi Fujikawa

Ryuzo Nishiyama

Isao Yokomichi

Nobuyuki Sakashita

Ryohei Takahashi

Yasuhiro Tsujii

Itaru Shigehara

Rikuo Nasu

Takahiro Haga

Shigeyuki Nishimura

Tadaaki Toki

Kuniaki Nagatani

Sinzo Someya

Mikio Miyaji

Fumio Kimura

Kazuyuki Maeda

Shinzo Someya

Hiroshi Yoshizawa

Toru Koyanagi

Shigeo Murai

Takao Awazu

Osamu Imai

Tatsuo Isogai

Terumasa Komyoji

Kouji Hayashi

Junichi Kawashima

Hisayoshi Jyonishi

Takeo Kaji

Toshihiko Yamamoto, Deceased

By Hikotaro Yamamoto, Legal Representative

Toshihiko Yamamoto

A trifluoromethylpyridine selected from the group consisting of .alpha.-trifluoromethylpyridine, .gamma.-trifluoromethylpyridine, a bis(trifluoromethyl)pyridine and chlorides thereof which have 1 to 3 chlorine atoms in its pyridine nucleus is produced by reacting a pyridine derivative selected from the group consisting of .alpha.-picoline, .gamma.-picoline and a lutidine with chlorine and anhydrous hydrogen fluoride at a temperature of 300.degree. to 600.degree. C. in a vapor phase in the presence of a diluent and a catalyst comprising a fluoride of a metallic element selected from the group consisting of aluminum, chromium, iron, nickel, manganese, cobalt and copper.

Process for producing trifluoromethylpyridines

A trifluoromethyl-2-(thio)pyridone compound having the formula: ##STR1## wherein X represents a hydrogen atom or a halogen atom, Y.sub.1 and Y.sub.2 each represents a hydrogen atom, a halogen atom or a trifluoromethyl group, and Z represents an oxygen atom or a sulfur atom, in which either Y.sub.1 or Y.sub.2 represents a trifluoromethyl group, and when X and Y.sub.2, or X and Y.sub.1 represent a hydrogen atom at the same time, then Z represents a sulfur atom, and a process for preparing the same.

Trifluoromethyl-2-pyridinone or pyridinthione compounds and process for

A process for producing a 3-chloro-5-trifluoromethylpyridine derivative comprises reacting a 5-trifluoromethylpyridine derivative having a hydrogen atom at 3-position with chlorine. The process is characterized by reacting said 5-trifluoromethylpyridine derivative with chlorine in a vapor phase in the presence of a catalyst selected from the group consisting of activated carbon and a chloride of a metal element selected from the group consisting of iron, antimony, copper and zinc.

Process for producing 3-chloro-5-trifluoromethylpyridines

A pyridine derivative having the formula ##STR1## wherein X.sup.2 and Y.sup.2 represents hydrogen atom or chlorine atom is produced by reacting a pyridine compound having the formula ##STR2## wherein X.sup.1 and Y.sup.1 represent hydrogen atom or chlorine atom, with chlorine and anhydrous hydrogen fluoride by a vapor phase reaction in the presence of a catalyst at a temperature of 250.degree. to 600.degree. C. using as the catalyst a fluoride of a metal selected from the group consisting of copper, vanadium, tin, bismuth, zirconium, magnesium, barium, zinc, calcium, potassium and sodium.

Process for producing a .beta.-trifluoromethylpyridine

A process for producing 2,6-difluorobenzonitrile comprises reducing a chloro fluorobenzonitrile selected from 3-chloro-2,6-difluorobenzonitrile, 3,5-dichloro-2,6-difluorobenzonitrile or a mixture thereof by hydrogen gas in the presence of a palladium or platinum catalyst at a temperature of 0.degree. to 200.degree. C.

Process for producing 2,6-difluorobenzonitrile

An aminobenzene is produced by reacting a chlorobenzene with ammonia in the presence of a copper type catalyst, namely by reacting ammonia with 3,5-diaminochlorobenzene to produce 1,3,5-triaminobenzene at a temperature of 150.degree. to 250.degree. C. at a molar ratio of ammonia of 2 to 10 to 3,5-diaminochlorobenzene in the presence of a copper compound catalyst.

Process for producing 1,3,5-triaminobenzene

1,3,5,-Trichlorobenzene is produced by chlorinating 1,3,5-trihalobenzene having 1 to 3 bromine atom and 2 to 0 chlorine atom. The gaseous 1,3,5-halobenzene having 1 to 3 bromine atom and 2 to 0 chlorine atom is brought into contact with chlorine gas at a molar ratio of 0.5 to 3.0 of the stoichiometric amount of chlorine required for said conversion, in a vapor phase at a temperature of 280.degree. to 500.degree. C.

Process for producing 1,3,5-trichlorobenzene

A 2-substituted-5-trifluoromethylpyridine compound represented by Formula (I): ##STR1## wherein X is a hydrogen atom or a halogen atom, and Y is a cyano group or a carboxy group, provided that Y is a cyano group, then X is a halogen atom, or a salt thereof, and a process for the production of the same. This compound is useful as an intermediate for the production of various fine chemicals.

2-Substituted-5-trifluoromethylpyridines and process for producing the

1-Bromo-3,5-dichlorobenzene is produced in high efficiency by a special isomerization of monobromodichlorobenzene in the presence of an aluminum halide and separating the object product and recycling a residue. 1-Bromo-3,5-dichlorobenzene is useful intermediates for various agricultural chemicals, dyes and medicines.

Process for producing 1-bromo-3,5-dichlorobenzene

.alpha.-[4-(4-Trifluoromethylphenoxy)phenoxy]alkanecarboxylic acids (the '4-trifluoromethylphenoxy group' of which may contain one chlorine atom as a substituent) and derivatives thereof useful as a herbicide, a herbicidal composition containing the compound, methods of controlling weeds and production thereof.

Herbicidal compound, herbicidal composition containing the same, and

A novel compound for combatting insect, mite, fungus or bacterium is a pyridylaniline represented by the following formula (I) ##STR1## wherein X is a trifluoromethyl group, a halogen atom, a lower alkyl group or a lower alkoxy group; n is an integer of 0 to 4; R is a hydrogen atom or an acetyl group; Y is a hydrogen atom, a halogen atom a lower alkoxy group, a lower alkylthio group, a hydroxy group, an azido group or a phenoxy group of which the phenyl ring may be substituted by a hydroxy group; Z.sub.1, Z.sub.2 and Z.sub.3 are a trifluoromethyl group or a nitro group, provided that at least one of X is a trifluoromethyl group or a lower alkyl group when n is an integer of 3 or 4.

Pyridylanilines

.alpha.[4-(4-Trifluoromethylphenoxy)phenoxy]alkanecarboxylic acids (the '4-trifluoromethylphenoxy group' of which may contain one chlorine atom as a substituent) and derivatives thereof useful as a herbicide, a herbicidal composition containing the compound, methods of controlling weeds and production thereof.

Pyridine derivatives having a trifluoromethyl group at .beta.-position thereof are produced by reacting .beta.-picoline with chlorine and hydrogen fluoride in a vapor phase at high temperature for a short time. The reaction condition can be mild and the yield of the object compound is increased by reacting them in the presence of a specific metal fluodie. The pyridine derivatives useful as starting materials for agricultural chemicals and medicines can be continuously obtained by a simple reaction at high yield.

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Moriyama, Japan

Kanichi Fujikawa