Sumitomo Chemical Company, Limited

Tomoyuki Kusaba

Masayo Sugano

Junya Takahashi

Masayuki Enomoto

Rei Matsunaga

Masahiro Tamaki

Yukio Oguri

Tamon Uematsu

Tomohiro Teramae

Kazuya Ujihara

Tsuguhiro Katoh

Akiko Kakimizu

Kimitoshi Umeda

Tadashi Ohsumi

Makoto Fujimura

Naoto Meki

Norio Kimura

Kenzi Takuma

Kazue Shinsugi

The purpose of the invention is to provide a process for advantageous production of dithiocarbonimide derivatives of the formula I: ##STR1##

Process for preparing dithiocarbonimide derivatives

The method for producing the benzyl bromide derivatives of the formula: ##STR1## wherein R.sub.1 represents a C.sub.1 to C.sub.5 alkyl group, which comprises reacting a 2-methylphenylacetic acid derivative of the formula: ##STR2## wherein R.sub.1 represents the same meaning above, with bromine in the presence of an alkali metal salt. In case that R.sup.1 is an ethyl or isopropyl group, the recrystallization of the above reaction product from aliphatic hydrocarbon solution gives the benzyl bromide derivatives efficiently and in high purity.

Method for producing benzyl bromide derivatives

There is disclosed a dithiocarbonimide derivative of the formula: ##STR1## wherein B is a C.sub.1 -C.sub.6 alkyl group; X is an NH group or an oxygen atom and Y is a nitrogen atom or a CH group, A is a phenyl group, a heterocyclic group, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group, a bicycloalkyl group or a tricycloalkyl group, all of which may be substituted. Also disclosed are a fungicidal/insecticidal/acaricidal agent containing the dithiocarbonimide derivative as an active ingredient, an intermediate for use in the production of the dithiocarbonimide derivative, and a process for producing the dithiocarbonimide derivative from the intermediate.

Dithiocarbonimide derivatives useful as acaricidal, fungicidal, and

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 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 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

An amide compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are, the same or different, each a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group and R.sup.3 is a 2-furyl group, a 3-furyl group, a 2-thienyl group or a 3-thienyl group, which is useful as an agricultural fungicide.

Amide derivatives, and their production and agricultural 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.

Growing community of inventors

Toyonaka, Japan

Tomoyuki Kusaba