Sumitomo Chemical Company, Limited

Yuji Funaki

Shizuya Tanaka

Toshiro Kato

Hirotaka Takano

Shigeo Yamamoto

Yukio Ishiguri

Hirofumi Oshita

Kazuo Izumi

Mitsuhiro Matsumoto

Masayuki Fukushima

Noritada Matsuo

Yukio Yoneyoshi

Yoshio Hisada

Kunihiko Furuzawa

Yukio Ishiguru

There is disclosed an imine compound of the general formula: ##STR1## wherein and R.sup.1 and R.sup.2 are, the same or different, each a C.sub.1 -C.sub.5 alkyl group, or R.sup.1 and R.sup.2 are combined together to form a C.sub.4 -C.sub.5 alkylene group; R.sup.3 is a C.sub.1 -C.sub.5 alkyl group, a C.sub.3 -C.sub.4 alkenyl group or a C.sub.3 -C.sub.4 alkynyl group, which is useful as an intermediate for production of agrochemicals and the like. Also disclosed are an amide compound useful as a raw material of the imine compound and production processes for these compounds.

Imine compounds and their production

There is disclosed an imine compound of the general formula: ##STR1## wherein R.sup.1 and R.sup.2 are, the same or different, each a C.sub.1 -C.sub.5 alkyl group, or R.sup.1 and R.sup.2 are combined together to form a C.sub.4 -C.sub.5 alkylene group; R.sup.3 is a C.sub.1 -C.sub.5 alkyl group, a C.sub.3 -C.sub.4 alkenyl group or a C.sub.3 -C.sub.4 alkynyl group, which is useful as an intermediate for production of agrochemicals and the like. Also disclosed are an amide compound useful as a raw material of the imine compound and production processes for these compounds.

A process for preparing a compound of the formula: ##STR1## in an excellent yield with high purity, which comprises reacting a compound of the formula: ##STR2## with 3,4,5,6-tetrahydrophthalic anhydride in the presence of a catalyst system consisting of a nitrogen-containing base and a lower fatty acid.

Production of tetrahydrophthalimide compound

The present invention relates to one of the two geometrical isomers (a compound defined as I-A isomer in the description below) of a triazole compound represented by the formula (I) or (II), ##STR1## wherein R.sub.1 is a hydrogen atom, a C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl or 2-propynyl group, R.sub.2 is a C.sub.1 -C.sub.6 alkyl, cyclopropyl or 1-methylcyclopropyl group, R.sub.3, which may be the same or different, is a halogen atom, a C.sub.1 -C.sub.4 alkyl, halogen-substituted C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.4 alkoxy, phenoxy, phenyl, cyano or nitro group, n is an integer of 0 to 3, and the term, halogen, means chlorine, bromine and fluorine atoms, its salts, production thereof and a fungicide, herbicide and/or plant growth regulator for agriculture and horticulture containing said compound as an active ingredient.

Geometrical isomer of 1-substituted-1-triazolystyrenes

A fungicidal composition which comprises an inert carrier and as an active ingredient (E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3- ol and a benzimidazole-thiophanate type fungicide in the ratio of 1 to 0.1 to 10 by part by weight in a total amount of 0.1 to 99.9% by weight.

Fungicidal composition

A fungicidal composition containing as an active ingredient a mixture of (E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3- ol and a member selected from an N, N'-ethylenebis(dithiocarbamate) fungicide, tetrachloroisophthalonitrile, N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfamide and an N-(3,5-dichlorophenyl)imide fungicide in the ratio of 1 to 0.5 - 20 by weight in a total amount of 0.1 to 99.9% by weight, and an inert carrier.

Fungicidal compositions containing mixtures of a substituted

Geometrical isomer of 1-substituted-1-triazolylstyrenes, and their

N-acylimidazole compounds represented by the formula: ##STR1## wherein X is halogen atom, or alkyl, alkoxy, lower alkylthio, halogen-substituted alkyl, phenyl, phenoxy, cyano, phenyl lower alkoxy or nitro group, R.sub.1 and R.sub.2, which may be the same or different, are hydrogen or halogen atom, or alkyl, lower alkenyl, lower alkoxy, trifluoromethyl, lower cycloalkyl lower alkyl or lower alkoxy lower alkyl group, or R.sub.1 and R.sub.2, taken together, may form lower alkylene or halogen-substituted lower alkylene group, m is 0 or 1, n is 0, 1 or 2, and when n is 2, (X).sub.2 groups may form methylenedioxy group, which compounds are useful for controlling plant-disease, regulating plant growth and controlling weeds.

Fungicidal N-(phenyl-lower alkanoyl-)-imidazole derivatives,

A fungicidal composition which comprises an inert carrier and as an active ingredient (E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3- ol and an N-haloalkylthioimide fungicide in the ratio of 1 to 0.1-20 by weight in a total amount of 0.1 to 99.9% by weight.

This invention relates to a triazolyl alcohol derivative having an optical activity of (-) or (+) and represented by the general formula (I), ##STR1## wherein X represents a hydrogen atom or a chlorine atom and the asterisk indicates an asymmetric carbon atom, a process for preparing same, and a fungicide containing same as active ingredient.

Optical isomer of triazolylpentenols, and their production and use as

A process for producing a triazolylvinyl ketone compound of the formula: ##STR1## wherein X is a hydrogen or chlorine atom, comprising heating a compound of the formula: ##STR2## wherein X is as defined above. The triazolylvinyl ketone compound is useful as agricultural fungicides.

Production of triazolylvinyl ketones

1-Phenyl-2-azolyl-4,4-dimethyl-1-penten-3-ols of the formula: ##STR1## wherein X, which may be same or different, is an alkyl (C.sub.1 -C.sub.4), cyano, alkoxy (C.sub.1 -C.sub.4), phenoxy, phenyl group, halogen atom, n is zero or an integer of 1 to 2, A.sub.Z is an imidazole group of the formula ##STR2## or a triazole group of the formula ##STR3## and salt thereof, which show high fungicidal activities without any material toxicity to mammals and plants and can be produced by reacting the corresponding 3-ketone compound with a reducing agent.

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Toyonaka, Japan

Yuji Funaki