Sumitomo Chemical Company, Limited

Junya Takahashi

Katsuzo Kamoshita

Toshiro Kato

Hiroshi Noguchi

Shigeo Yamamoto

Yukio Oguri

Masayo Sugano

Tomoyuki Kusaba

Masayuki Enomoto

Rei Matsunaga

Masahiro Tamaki

Naonori Hirata

Mitsuru Sasaki

Yukio Ishiguri

Kiyoshi Higashi

Yoshitaka Tomigahara

Ryo Yoshida

Ichiki Takemoto

Seizo Sumida

Tadashi Ooishi

Hiroki Tomioka

Tamon Uematsu

Tomohiro Teramae

Haruhiko Katoh

Shigeko Nakamura

Chizuko Takahashi

Ryo Sato

Hiroaki Fujimoto

Toru Haga

Sumio Nishida

Izumi Fujimoto

Masaharu Sakaki

Yoshinori Shono

The present invention relates to a cinnamoyl compound represented by the formula (I): 

Cinnamoyl derivatives and use thereof

Cinnamoyl compound and use of the same

A benzimidazole derivative having the formula, ##STR1## wherein R is cyano or thiocarbamoyl; Q is lower alkyl or a group represented by the formula NQ.sup.1 Q.sup.2, in which Q.sup.1 and Q.sup.2 are independently lower alkyl, lower alkyl substituted with phenyl, lower alkenyl or lower alkynyl, or they form a lower alkylene ring when taken together at their ends which ring may include a hereto atom; X is hydrogen or halogen; and Z is a group which consists of (a) one oxygen atom or two non-adjacent oxygen atom, (b) --CF.sub.2 -- group and (c) any one of a single bond, --CF.sub.2 --, --CFH--, CFCl-- and --CH.sub.2 -- groups and forms a five-membered or six membered ring together with two adjacent carbon atoms of the benzene ring; is obtained by reacting a corresponding 2-cyanobenzimidazole compound and a sulfamoyl chloride derivative. The benzimidazole derivative is incorporated into agricultural and horticultural fungicides as an active ingredient.

Benzimidazole derivatives, agricultural and horticultural fungicides

A benzimidazole derivative having the formula, ##STR1## wherein R is cyano or thiocarbamoyl; Q is lower alkyl or a group represented by the formula NQ.sup.1 Q.sup.2, in which Q.sup.1 and Q.sup.2 are independently lower alkyl, lower alkyl substituted with phenyl, lower alkenyl or lower alkynyl, or they form a lower alkylene ring when taken together at their ends which ring may include a hetero atom; X is hydrogen or halogen; and Z is a group which consists of (a) one oxygen atom or two non-adjacent oxygen atom, (b) --CF.sub.2 --group and (c) any one of a single bond, --CF.sub.2 --, --CFH--, CFCl-- and --CH.sub.2 --groups and forms a five-membered or six membered ring together with two adjacent carbon atoms of the benzene ring; is obtained by reacting a corresponding 2-cyanobenzimidazole compound and a sulfamoyl chloride derivative. The benzimidazole derivative is incorporated into agricultural and horticultural fungicides as an active ingredient.

Benzimidazole derivatives agricultural and horticultural fungicides

A compound of the formula: ##STR1## wherein X is an oxygen atom or a sulfur atom, Y is a hydrogen atom or a fluorine atom, Z is a methylene group or a group of the formula: N--R.sub.5 (in which R.sub.5 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.7 alkenyl group, a C.sub.3 -C.sub.7 alkynyl group, a halo(C.sub.2 -C.sub.6)alkyl group or a C.sub.1 -C.sub.6 alkoxycarbonylmethyl group), R.sub.1 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.7 alkenyl group, a C.sub.3 -C.sub.7 alkynyl group, a halo(C.sub.2 -C.sub.6)alkyl group, a halo(C.sub.3 -C.sub.7)alkenyl group, a cyano(C.sub.1 -C.sub.6)alkyl group, a C.sub.1 -C.sub.6 alkoxy(C.sub.1 -C.sub.6)alkyl group or a C.sub.1 -C.sub.6 alkoxycarbonylmethyl group, R.sub.2 is a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group; R.sub.3 and R.sub.4 are, the same or different, each is a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group; n is an integer of 0 or 1, which is useful as a herbicide.

N-phenylimides, and their production and use

A benzimidazole derivative having the formula, ##STR1## wherein R is cyano or thiocarbamoyl; Q is lower alkyl or a group represented by the formula NQ.sup.1 Q.sup.2, in which Q.sup.1 and Q.sup.2 are independently lower alkyl, lower alkyl substituted with phenyl, lower alkenyl or lower alkynyl, or they form a lower alkylene ring when taken together at their ends which ring may include a hetero atom; X is hydrogen or halogen; and Z is a group which consists of (a) one oxygen atom or two non-adjacent oxygen atom, (b) --CF.sub.2 -- group and (c) any one of a single bond, --CF.sub.2 --, --CFH--, CFCl-- and --CH.sub.2 -- groups and forms a five-membered or six membered ring together with two adjacent carbon atoms of the benzene ring; is obtained by reacting a corresponding 2-cyanobenzimidazole compound and a sulfamoyl chloride derivative. The benzimidazole derivative is incorporated into agricultural and horticultural fungicides as an active ingredient.

A benzimidazole derivative having the formula, ##STR1## wherein X is halogen, is produced by reacting a compound having the formula, ##STR2## wherein X is halogen, with dimethylsulfamoyl chloride. The benzimidazole derivative can be used as an active ingredient in agricultural and horticultural fungicides.

Benzimidazole derivative, its intermediate compounds and an agricultural

A soil disease controlling agent for preventing and controlling diseases caused by pathogenic fungi living in soil, which comprises an effective amount of at least one of a 2-cycloalkenylamine derivative and its salts as an active ingredient, and at least one inert carrier or diluent.

Soil disease-controlling cyano and ester derivatives of cyclopentenyl

An insecticidal and/or acaricidal composition which comprises as an active ingredient an insecticidally and/or acaricidally effective amount of at least one ether compound of the formula: ##STR1## wherein X.sub.1 is a hydrogen atom, a halogen atom, a lower alkyl group, a halo(lower)alkyl group, a phenoxyphenoxy(lower)alkyl group, a lower alkoxy group, a halo(lower)alkoxy group, a phenyl group, a halo(lower)alkoxyphenyl group, a methylenedioxy group or a group of the formula: ##STR2## (in which ##STR3## is a 6-membered unsaturated ring, X.sub.2 is a hydrogen atom, a halogen atom or a halo(lower)alkoxy group, Y.sub.2 is a hydrogen atom or combined with Y.sub.1 to form a direct single bond, n is an integer of 1 or 2 and X is an oxygen atom, a sulfur atom, a carbonyl group or a group of the formula: --C(R.sub.3)(R.sub.4)-- (in which R.sub.3 and R.sub.4 are each a hydrogen atom or a lower alkyl group));

Ether compounds and their production, and insecticidal and/or acaricidal

A compound of the formula: ##STR1## wherein X is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.3 alkyl group or a C.sub.1 -C.sub.3 alkoxy group and Y is a hydrogen atom, a halogen atom, a cyano group, a formyl group, an ethylene-dioxymethyl group, a hydroxyl group, a hydroxymethyl group or a group of either one of the formulas: --CH.dbd.N--OR.sup.1, --COOR.sup.2, --CONH--R.sup.2 and --CH(OR.sup.3).sub.2 in which R.sup.1 is a hydrogen atom, a C.sub.1 -C.sub.3 alkyl group, a C.sub.3 -C.sub.5 alkenyl group, a C.sub.3 -C.sub.5 alkynyl group, a halo(C.sub.3 -C.sub.5)alkynyl group or a C.sub.1 -C.sub.3 alkyl group substituted with a phenyl group or a cyano group, R.sup.2 is a hydrogen atom, a C.sub.1 -C.sub.3 alkyl group, a C.sub.3 -C.sub.5 alkenyl group or a C.sub.3 -C.sub.5 alkynyl group and R.sup.3 is a C.sub.1 -C.sub.3 alkyl group, with the proviso that X and Y are not simultaneously hydrogen atoms, which is useful as a fungicidal agent against phytopathogenic fungi, particularly their strains resistant to benzimidazole or thiophanate fungicides and/or cyclic imide fungicides.

Dipropargyloxybenzene compounds and their production

A fungicidal composition which comprises as an active ingredient a fungicidally effective amount of the compound represented by the general formula, ##STR1## wherein X, which may be the same or different, represents a hydrogen or halogen atom or a lower alkyl group, R.sup.1 and R.sup.2, which may be the same or different, represent a hydrogen atom or a methyl group, and n represents an integer of from 1 to 5, and an inert carrier.

Fungicidal composition

A compound of the formula: ##STR1## wherein X is a halogen atom and Y is a C.sub.1 -C.sub.4 alkyl group, a C.sub.2 -C.sub.4 alkenyl group, a C.sub.1 -C.sub.3 alkoxy group, a C.sub.3 -C.sub.4 alkenyloxy group, a C.sub.3 -C.sub.4 alkynyloxy group, a C.sub.2 -C.sub.3 alkenyl group substituted with phenyl, a C.sub.3 -C.sub.4 alkenyloxy group substituted with halogen, a C.sub.1 -C.sub.3 alkoxy group substituted with one member selected from the group consisting of halogen, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkanoyl, cyano, hydroxycarbonyl, C.sub.1 -C.sub.3 alkylaminocarbonyl and phenyl, or a group of the formula: --CH.sub.2 O--R.sup.1, --CH.dbd.CH--R.sup.2, --CH.dbd.N--R.sup.3 or --CO--R.sup.4 in which R.sup.1 is a C.sub.1 -C.sub.3 alkyl group, a C.sub.3 -C.sub.4 alkenyl group or a C.sub.3 -C.sub.4 alkynyl group, R.sup.2 is a cyano group, a methoxycarbonyl group or an acetyl group, R.sup.3 is a dimethylamino group or a phenyl group and R.sup.4 is a C.sub.1 -C.sub.2 alkyl group, which is useful as a fungicidal agent against phytopathogenic fungi, particularly strains resistant to benzimidazole or thiophanate fungicides and/or cyclic imide fungicides.

A compound having a fungicidal activity represented by the general formula, ##STR1## wherein X, which may be the same or different, represents a cyano, nitro, halogenated lower alkyl, C.sub.1 -C.sub.12 alkoxy, lower alkoxy-substituted lower alkyl, lower alkenyloxy, lower alkynyloxy, halogenated lower alkoxy, lower alkoxycarbonyl or lower alkylthio group, R.sup.1 and R.sup.2, which may be the same or different, represent a hydrogen atom or a methyl group, Y represents a hydrogen or chlorine atom, m represents an integer of from 1 to 5, and n represents an integer of from 0 to 4, the sum of m and n being less than 6.

Iodopropargyl carbamate derivative, a method for its production and

A compound of the formula: ##STR1## useful as a fungicidal agent against phytopathogenic fungi, particularly their strains resistant to benzimidazole, thiophanate and/or cyclic imide fungicides.

Growing community of inventors

Hyogo, Japan

Junya Takahashi