Ishihara Sangyo Kaisha, Ltd.

Yasuhiro Tsujii

Kanichi Fujikawa

Isao Yokomichi

Ryuzo Nishiyama

Shigeyuki Nishimura

Tatsuo Isogai

Nobuyuki Sakashita

Ryohei Takahashi

Itaru Shigehara

Shigeo Murai

Takao Awazu

Tokiya Kimura

Takahiro Haga

Kuniaki Nagatani

Toshihiro Tanaka

Hisayoshi Jyonishi

Hiroshi Yoshizawa

Hiroshi Sasaki

Hisayoshi Jonishi

Mikio Miyaji

An aminocarbonyl-substituted pyridinesulfinic acid intermediate for production of an herbicide having formula (V): ##STR1## wherein R.sub.3 and R.sub.4 are selected from the group consisting of hydrogen and alkyl groups, or a salt thereof. The aminocarbonyl-substituted pyridinesulfinic acid or salt thereof is useful as the precursor of aminosulfonyl-substituted pyridinecarbonic acid amide, which in turn is useful as the starting material for agricultural chemicals, medicine, etc.

Mercapto-substituted pyridine compounds, aminocarbonyl-substituted

The present invention relates to an industrially advantageous process for producing 2-amino-4,6-dichloropyrimidine, which comprises reacting 2-amino-4,6-dihydroxypyrimidine or its salt with phosphorus oxychloride at a temperature of from 50.degree. to 100.degree. C. in the presence of a solvent and an acid removing agent. Further, the yield of 2-amino-4,6-dichloropyrimidine can be improved by hydrolyzing 4,6-dichloro-2-pyrimidinylphosphoramidic dichloride produced as a by-product of the chlorination reaction to form 2-amino-4,6-dichloropyrimidine. The 2-amino-4,6-dichloropyrimidine produced by the process of the present invention is useful as an intermediate for medicines and agricultural chemicals.

Process for producing 2-amino-4,6-dichloropyrimidine

A novel amino-trifluoromethylpyridine compound selected from the group consisting of 3-amino-5-trifluoromethylpyridine, 2-amino-4-trifluoromethylpyridine, and 2-amino-4,6-bis(trifluoromethyl)pyridine, and, a process for preparing the same by reacting a halogeno-trifluoromethylpyridine compound with ammonia at a temperature of 50.degree. to 200.degree. C. The compound is useful as an intermediate from which a compound effective in controlling various harmful organisms or an effective component compound of medicines can be easily derived.

Amino-trifluoromethylpyridine compound

A process for preparing a S-substituted phosphorochloridothiolate having the formula: ##STR1## wherein R.sup.1 is a chlorine atom or an alkoxy or phenoxy group which may be substituted, and R.sup.2 is an alkyl, alkenyl, alkynyl, cycloalkyl or phenyl group which may be substituted, which comprises isomerizing an O-substituted phosphorochloridothionate having the formula: ##STR2## wherein R.sup.1 and R.sup.2 are as defined above, in the presence of a Lewis acid catalyst or a phosphorus compound catalyst.

Process for preparing a S-substituted phosphoro-chloridothiolate

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 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

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

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.

Process for producing pyridine derivatives having a trifluoromethyl

A chloro .beta.-trifluoromethylpyridine is produced by reacting a chloro .beta.-trichloromethylpyridine with hydrogen fluoride in the presence of a specific metal fluoride in a vapor phase at high temperature for a short time. The chloro .beta.-trifluoromethylpyridines which are useful as intermediates for agricultural chemicals and medicines can be obtained at high yield.

Process for producing chloro .beta.-trifluoromethylpyridines

1-Bromo-3,5-dichlorobenzene is reacted with magnesium in a solvent and acetone is added to react it with the reaction product and a mineral acid is added to hydrolyze the resulting .alpha.-(3,5-dichlorophenyl) isopropoxymagnesium bromide and then, the product is dehydrated to obtain 3,5-dichloro-.alpha.-methylstyrene. 3,5-Dichloro-.alpha.-methylstyrene is useful intermediate for various agricultural chemicals, medicines and dyes and also useful monomer for rubbers, plastics and resins.

Process for producing 3,5-dichloro-.alpha.-methylstyrene

3,5-Dichloroaniline is advantageously produced by reacting 1-bromo-2,4-dichlorobenzene with a metal amide in liquid ammonia at a molar ratio of 1-bromo-2,4-dichlorobenzene to the metal amide of 1 : 2 to 7. The 3,5-dichloroaniline is useful as an intermediate for various agricultural chemicals, dyes and medicines.

Process for producing 3,5-dichloroaniline from

.alpha.-[4-(5-Mono-substituted or 3,5-di-substituted-pyridyl-2-oxy)phenoxy]alkanecarboxylic acids and derivatives thereof useful as a herbicide; a herbicidal composition containing the compound; methods of controlling weeds using such materials and production of such materials.

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Kusatsu, Japan

Yasuhiro Tsujii