Kureha Kagaku Kogyo Kabushiki Kaisha

Kureha Kagaku Kogyo K.k.

Kureha Chemical Industry Company, Limited

Kureha Corporation

Meiji Seika Pharma Co., Ltd.

Gifu University

Kureha Kagahu Kogyo K.k.

Satoru Kumazawa

Toshihide Saishoji

Atsushi Ito

Susumu Shimizu

Nobuo Sato

Hiroyuki Enari

Shiro Yamazaki

Takafumi Shida

Katsumichi Aoki

Susumu Ikeda

Hideo Arabori

Hiroyasu Shinkawa

Keigo Satake

Tsuneaki Chida

Yohichi Kanda

Takeo Watanabe

Masanori Minoguchi

Masato Arahira

Takashi Kimura

Kazuhiko Sunagawa

Nobuyuki Kusano

Hajime Hoshi

Eisaku Takahashi

Masahiro Hamada

Katsuhisa Ohsugi

Eyji Yoshida

Shinzo Kagabu

Shoichiro Hayashi

Masayoshi Hatanaka

Heitaro Obara

Masashi Ohtsuru

Takayoshi Eizuka

Shigeru Mizusawa

Isao Ichinose

Susumu Shimizue

Takeo Watanave

Masatoshi Sano

Eizi Yokoyama

Tsutomu Takagi

Keiichi Sudo

Masaru Mori

Toshihide Saishojo

Tsumoru Watanabe

Yoshitaka Niizeki

[Technical Problem] To provide a novel imino derivative capable of being an insecticide compound having excellent characteristics such as sustained effects and broad spectrum. [Solution to Problem] To provide an imino derivative represented by Formula (1). wherein 'Ar' denotes a heterocyclic group which may have a substituent on the ring; 'X' denotes a sulfur atom or CH, NR; &#x201c;R&#x201d; denotes a hydrogen atom or an alkyl group; &#x201c;Y&#x201d; is selected from CORor CONRR, CONHCOR, COR; and each of &#x201c;R&#x201d;, &#x201c;R&#x201d;, &#x201c;R&#x201d;, &#x201c;R&#x201d;, and &#x201c;R&#x201d; denotes a hydrogen atom or a certain substituent.

Imino derivatives, methods for producing the same and insecticides containing the same

5-[(4-chlorophenyl)methyl]-2,2-dimethylcyclopentanone is produced by

Process for the preparation of 5-[(4-chlorophenyl)methyl]-2,2-dimethylcyclopentanone

N-heterocyclicmethylpropylamine derivatives of formula (I):

N-heterocyclic methylpropylamine derivatives, process for producing the same and germicides

The present invention provides a process for producing alkylcyclopentanone derivatives of formula (1) by reacting alkyl cyclopentanone derivatives of formula (2) and alkyl halides of formula (3) in an organic solvent in the presence of molecular sieves and an alkaline metal hydroxide: ##STR1## wherein R.sup.1 is C.sub.1 -C.sub.4 alkyl group; R.sup.2 is hydrogen atom or C.sub.1 -C.sub.5 alkyl group; R.sup.3 is C.sub.1 -C.sub.5 alkyl group; Y is halogen atom, C.sub.1 -C.sub.5 alkyl group, C.sub.1 -C.sub.5 haloalkyl group, phenyl group, cyano group or nitro group; n is an integer from 0 to 5; when n is 2 or greater, Y's may be identical or different; R.sup.3 in formula (3) is the same as R.sup.3 in formula (1); and a process for preparing alkylcyclopentanone derivatives of formula (5) by reacting cyclopentanone derivatives of formula (4) and alkyl halides of formula (6) in an organic solvent in the presence of molecular sieves and an alkaline metal hydroxide: ##STR2## wherein R.sup.1 is C.sub.1 -C.sub.4 alkyl group; R.sup.4 is hydrogen atom or C.sub.1 -C.sub.5 alkyl group; R.sup.5 is C.sub.1 -C.sub.5 alkyl group; R.sup.k is either R.sup.4 or R.sup.5 ; Y is halogen atom, C.sub.1 -C.sub.5 alkyl group, C.sub.1 -C.sub.5 haloalkyl group, phenyl group, cyano group or nitro group; n is an integer from 0 to 5; when n is 2 or greater, Y's may be identical or different.

Process for the producing of alkylcyclopentanone derivatives

Derivatives of alkyl 3-(substituted or unsubstituted benzylidene)-1-alkyl-2-oxocylopentanecarboxylate of the following formula (I), ##STR1## wherein R.sup.1 and R.sup.2 individually represent a lower alkyl group; X is a halogen atom, a cyano group, an alkyl group, a haloalkyl group, a phenyl group, or a nitro group; and m is an integer of 0 to 5; provided when m is 2 or larger, Xs may be either the same or different. The compounds are useful themselves as an effective ingredient of antifungal compositions, and can be used for intermediates of agriculture chemicals and medicines.

Alkyl 3-(substituted or unsubstituted

Disclosed herein is a method for preventing deterioration of an industrial material by using an azole derivative represented by the following formula ##STR1## wherein X means a halogen atom or a C.sub.1 -C.sub.5 alkyl, haloalkyl, phenyl, cyano or nitro group, n stands for 0 or an integer of 1-5, A denotes a nitrogen atom or CH, R.sub.1 and R.sub.2 mean individually a hydrogen atom or a C.sub.1 -C.sub.5 alkyl group, R.sub.3 denotes a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group, and when n is an integer of 2-5, Xs may be the same or different. A biocidal composition for the method is also disclosed.

Biocidal compositions for industrial materials

In the present invention, an optically active cis type 1,2-diol derivative of the following formula (I) is produced by reacting a cis type 1,2-diol derivative of the formula (I) with a carboxylic acid derivative of the formula (II) in the presence of a lipase: ##STR1## wherein R.sup.1 and R.sup.2 independently represent hydrogen atom or an alkyl group, X represents a halogen atom, a nitro group, a cyano group, an alkyl group, a haloalkyl group, or a phenyl group, and n represents an integer of from 0 to 5; R.sup.3 represents a C.sub.1 -C.sub.10 alkyl group or an aryl group, and R.sup.4 represents a hydrogen atom, a C.sub.1 -C.sub.5 alkyl group, a C.sub.2 -C.sub.4 alkenyl group, or COR.sub.3. The cis type means that the bond between the cyclopentane ring and the hydroxy group and the bond between the cyclopentane ring and the benzyl group reside in the same direction as that portrayed on the paper. The optically active cis type 1,2-diol derivative is used as an intermediate for producing an optically active cis type azole derivative of the formula (VII).

Process for separating optically active 1-hydroxy-cyclopentane methanol

This invention provides a process for producing an optically active 1,2-diol derivative by optical resolution. The optically active 1,2-diol derivative of the formula (I) which is capable of utilizing as an intermediate of fungicidal optically-active azole derivatives can be produced by esterifying a 1,2-diol derivative of the formula (I) as a substrate with a carboxylic acid derivative of the formula (II) as a reagent in the presence of a lipase as a catalyst. ##STR1## wherein R.sup.1 is C1-C5 alkyl group, C3-C7 cycloalkyl group or C1-C5 haloalkyl group, R.sup.2 is C1-C3 alkyl group substituted by a phenyl group which may have one or two halogen atoms and/or C1-C4 alkyl groups, C2-C3 alkenyl group substituted by a phenyl group which may have one or two halogen atoms and/or C1-C4 alkyl groups, or C1-C3 alkyl group substituted by a phenoxy group which may have one or two halogen atoms and/or C1-C4 alkyl groups, R.sup.3 is C1-C10 alkyl group or aryl group, and R.sup.4 is hydrogen atom, C1-C5 alkyl group, C2-C4 alkenyl group or COR.sub.3.

Process for optical resolution of 1,2-diol derivatives

This invention provides a simple process for production of an (azolylmethyl)(biphenylmethyl)cyclopentanol derivative represented by the following formula (I) in a good yield. This process comprises, as described in the following reaction formula, reacting an (azolylmethyl)(halogenophenylmethyl)cyclopentanol derivative represented by the following formula (II) with a benzene derivative represented by the following formula (III) by light irradiation. ##STR1## wherein X denotes a halogen atom, R.sup.1 and R.sup.2 denote independently a hydrogen atom or a C1-C5 alkyl group, R.sup.3 denotes a C1-C5 alkyl group, n means an integer of 0-2, and A represents CH or N.

Process for production of (azolylmethyl)-(biphenylmethyl)cyclopentanol

A process for preparing a derivative of azolylmethylcycloalkanol of the following formula (I) comprising, providing a solid-liquid two-phase mixture of a cycloalkanone derivative of formula (II), an azole compound of formula (III), a metal oxide of formula (IV), and an organic solvent, and adding a sulfonium compound of formula (V) to said solid-liquid two-phase mixture under heating while stirring, ##STR1## wherein R.sup.1 and R.sup.2 individually represent a hydrogen atom or an alkyl group; X is a halogen atom, an alkyl group, a haloalkyl group, a phenyl group, a cyano group, or a nitro group; m is an integer of 0 to 5 (when m is 2 or larger, Xs may be either the same or different); n is an integer of 0 to 2; A represents a nitrogen atom or a group CH; M.sup.1 represents an alkali metal atom or an alkaline earth metal atom; M.sup.2 represents an alkaline earth metal atom, a zinc atom, or two alkali metal atoms; Y represents a halogen atom or a C.sub.1 -C.sub.4 alkoxysulfonyloxy group; and p denotes an integer of 0 or 1.

Process for preparation of azolylmethylcycloalkanol derivatives

A process for separating a cis isomer from a mixture of the cis isomer and a trans isomer of an azolylmethylcyclopentanol derivative of the formula (I): ##STR1## wherein, R.sup.1 and R.sup.2 each independently represent a hydrogen atom or an alkyl group; each X represents a halogen atom, an alkyl group, a haloalkyl group, a phenyl group, a cyano group or a nitro group; n is an integer of from 0 to 5; A represents a nitrogen atom or a CH group; and each X may be identical or different when n is an integer of from 2 to 5, comprising the steps of dehydrating selectively the trans isomer in the presence of an acid and isolating the cis isomer.

Process for separating isomers of azolylmethylcyclopentanol derivatives

Disclosed herein are an azole derivative represented by the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 respectively represent a (C.sub.1 -C.sub.5) alkyl group or a hydrogen atom; X represents a halogen atom, a (C.sub.1-C.sub.5) alkyl group or a phenyl group; n represents an integer of from 0 to 2 and A represents a nitrogen atom or a CH, provided that R.sup.1 is not a hydrogen atom when R.sup.2 is a hydrogen atom, a process for producing the azole derivative represented by the formula (I), and an agricultural and horticultural composition containing the azole derivative represented by the formula (I).

Cyclopentanecarboxylic acid derivatives useful for producing azole

Disclosed herein is a process for preparing a cis-azole derivative represented by the general formula (I) ##STR1## wherein R.sup.1 and R.sup.2 denote each a hydrogen atom or an alkyl group, R denotes a halogen atom, a nitro group, a cyano group, an alkyl group, a haloalkyl group or a phenyl group, A denotes a nitrogen atom or a methine group, and n stands for an integer of 1-5, which comprises reducing an azolylmethyloxabicyclohexane derivative represented by the general formula (VI) ##STR2## wherein R.sup.1, R.sup.2, R, A and n have the same meanings as defined above. A fungicidal composition comprising the azolylmethyloxabicyclohexane derivative represented by the above-mentioned general formula (VI) is also desclosed.

Cis-azole derivatives, intermediates thereof and fungicidal compositions

Azole derivatives for protecting industrial materials from bacteria

The present invention discloses an azole-substituted cycloalkanol derivative represented by the formula (I) available for agricultural and horticultural fungicide and a process for preparing the same: ##STR1## wherein R.sup.1 represents a lower alkyl group, R.sup.2 represents a hydrogen atom or a lower alkyl group, n is an integer of 1 or 2 and A represents a nitrogen atom or a CH group.

Imidazole substituted cycloalkanol derivatives and fungicidal

Growing community of inventors

Iwaki, Japan

Satoru Kumazawa