Sumitomo Chemical Company, Limited

Hisami Takeda

Masachika Hirano

Nobuo Ohno

Takashi Matsuo

Toshio Mizutani

Yoshitoshi Okuno

Toshio Nishioka

Isao Ohno

Nobushige Itaya

Kiyoshi Kasamatsu

Shigeyoshi Kitamura

Kunio Mukai

Osamu Magara

Toshiro Kato

Kozo Tsuji

Naonori Hirata

Toshihiko Yano

Mitsuru Sasaki

Toshiro Ohtsubo

Hiroki Tomioka

Shigenori Tsuda

Osamu Kirino

Takeo Satomi

Yukio Manabe

Minoru Ueda

Shigehiro Ooba

Norbushige Itaya

A microencapsulated insecticidal composition has excellent residual effect which comprises an organophosphorus insecticide encapsulated in a wall formed of a polyurea and having an average particle diameter of not more than 80 .mu.m, a wall thickness of not more than 0.3 .mu.m and a ratio of an average particle diameter/wall thickness of not less than 250.

Microencapsulated organophosphorus insecticidal composition for

A bromodichloroimidazole derivative represented by the formula ##STR1## wherein R represents a C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.5 alkyl substituted by one or more halogen atoms, C.sub.3 alkenyl, C.sub.3 alkenyl substituted by one or more halogen atoms, C.sub.3 alkynyl or C.sub.3 alkynyl group substituted by one or more halogen atoms; its production; and an insecticidal and/or acaricidal composition containing it as an active ingredient.

Bromodichloroimidazole insecticide

Amide phosphorothiolate derivatives of the formula, ##STR1## wherein X is an oxygen or sulfur atom, Y is an oxygen or sulfur atom or imino group, R.sub.1 and R.sub.2, which may be the same or different, are each a C.sub.1 -C.sub.3 alkyl group, R.sub.3 is a C.sub.1 -C.sub.4 alkyl group, R.sub.4 is a hydrogen atom or methyl group, R.sub.5 is a C.sub.1 -C.sub.3 alkyl, methoxy or ethoxy group, Z is a hydrogen atom, a methyl group or chlorine atom and n is 1 or 2, a process for producing said derivatives characterized by reacting the salt of thiophosphoric ester represented by the formula, ##STR2## wherein X, Y, R.sub.1 and R.sub.2 are as defined above and M is a sodium or potassium atom or ammonium group, with a haloacetamide derivative of the formula, ##STR3## wherein R.sub.3, R.sub.4, R.sub.5, Z and n are as defined above and W is a halogen atom, and a combined insecticide, acaricide, nematocide and/or fungicide containing said derivatives as an active ingredient.

Amide phosphorothiolate derivatives and their use as pesticides

A novel substituted-arylacetic acid ester of the formula, ##STR1## wherein R.sub.1 and R.sub.2 are each hydrogen or a halogen atom, a C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.1 -C.sub.4 alkoxy, cyano, nitro, methylthio, C.sub.1 -C.sub.4 alkanoyl, C.sub.1 -C.sub.4 alkanoyloxy, or C.sub.1 -C.sub.4 alkoxycarbonyl group, or R.sub.1 and R.sub.2, taken together, may form methylenedioxy, a C.sub.3 -C.sub.5 alkylene or butadienylene (--CH.dbd.CH--CH.dbd.CH--) ring; R.sub.3 is a C.sub.2 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, propargyl, C.sub.3 -C.sub.6 cycloalkyl or cyclopropylmethyl group; R.sub.4 is hydrogen or a halogen atom, methyl or ethyl group; R.sub.5 is allyl, propargyl, 3-butenyl, 3-butynyl, phenyl or benzyl group; and A is oxygen or sulfur atom or --CH.dbd.CH-- group, which possesses various useful insecticidal and acaricidal activities and can be prepared by reacting a substituted-arylacetic acid of the formula: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and A are each as defined above, or a reactive derivative thereof with an alcohol, or halide or sulfonate thereof of the formula, ##STR3## wherein R.sub.4 and R.sub.5 are each as defined above and X is hydroxy group, a halogen atom, alkylsulfonyloxy or arylsulfonyloxy group.

Substituted-acetic acid ester

Novel alkynylcyclopropanecarboxylic acid esters represented by the formula, ##STR1## wherein R.sub.1 represents hydrogen, halogen, lower alkyl having up to 5 carbon atoms, lower alkenyl having up to 5 carbon atoms, lower alkynyl having up to 5 carbon atoms, C.sub.1 -C.sub.4 alkoxy C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio C.sub.1 -C.sub.4 alkyl, aryl, aryl C.sub.1 -C.sub.4 alkyl, furyl, substituted furyl, thienyl, substituted thienyl, furfuryl, substituted furfuryl, thenyl, substituted thenyl, cyclo C.sub.3 -C.sub.6 alkyl, substituted cyclo C.sub.3 -C.sub.6 alkyl, cyclo C.sub.3 -C.sub.6 alkenyl or substituted cyclo C.sub.3 -C.sub.6 alkenyl; R.sub.2 and R.sub.3 individually represent hydrogen, halogen, lower alkyl having up to 5 carbon atoms, lower alkenyl having up to 5 carbon atoms, lower alkynyl having up to 5 carbon atoms, aryl, aryl C.sub.1 -C.sub.4 alkyl or may form a carbon-carbon bond; or R.sub.1 and R.sub.3 are bonded to each other at the ends to form a polymethylene chain containing or not containing an oxygen or a sulfur atom, or R.sub. 1 and R.sub.2 are bonded to each other at the ends to form a polymethylene chain containing or not containing an oxygen or a sulfur atom; R.sub.4 represents hydrogen or methyl; R.sub.5 represents hydrogen, methyl, vinyl, 1-propenyl, 2-methyl-1-propenyl, 2-methoxymethyl-1-propenyl, 2-methoxycarbonyl-1-propenyl, 2,2-dichlorovinyl or cyclopentylidenemethyl when R.sub.4 is hydrogen, and R.sub.5 represents methyl when R.sub.4 is methyl; and R.sub.6 and R.sub.7 represent hydrogen or methyl. These novel esters are produced by reacting an alcohol or its halide or arylsulfonate of the formula, ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.6 are as defined above, and A is hydroxy, halogen or arylsulfoxy, with a cyclopropanecarboxylic acid of the formula, ##STR3## wherein R.sub.4, R.sub.5 and R.sub.7 are as defined above, or its reactive derivative. These esters are useful as an insecticide harmless to mammals.

Acetylenic secondary alcohols

Novel alkynyl esters of cyclopropanecarboxylic acid represented by the formula, ##STR1## wherein R.sub.1 represents hydrogen, lower alkyl having 1-4 carbon atoms, lower alkenyl having 2-4 carbon atoms, lower alkynyl having 2-4 carbon atoms, C.sub.1 -C.sub.2 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.2 alkylthio-C.sub.1 -C.sub.4 alkyl, furyl, thienyl, furfuryl, thenyl, cyclo-C.sub.3 -C.sub.6 alkyl, oxygen atom-containing cyclo-C.sub.3 -C.sub.6 alkyl, cyclo-C.sub.5 -C.sub.6 alkenyl, oxygen atom-containing cyclo-C.sub.4 -C.sub.6 alkenyl, halo-C.sub.2 -C.sub.4 alkenyl, phenyloxymethyl, phenylthiomethyl, cyclo-C.sub.5 -C.sub.6 alkenylmethyl, oxygen atom-containing cyclo-C.sub.4 -C.sub.6 alkenylmethyl, cyclo-C.sub.5 -C.sub.6 alkylmethyl, oxygen atom-containing cyclo-C.sub.4 -C.sub.6 alkylmethyl or ##STR2## IN WHICH X is halogen, nitro, cyano, methylenedioxy, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 alkoxy, dimethylamino, m is 0, 1, 2 or 3, n is 0, 1, 2 or 3 and each X may be different when n is 2 or 3; R.sub.2 and R.sub.3 individually represent hydrogen, halogen (except R.sub.2), phenyl, benzyl, lower alkyl having 1 - 3 carbon atoms, lower alkenyl having 2 - 3 carbon atoms, lower alkynyl having 2 - 3 carbon atoms or may form a carbon-carbon bond or are bonded to each other at the ends to form C.sub.3 -C.sub.4 polymethylene chain, or R.sub.1 and R.sub.2 are bonded to each other at the ends to form C.sub.5 polymethylene chain; R.sub.4 represents hydrogen or methyl; R.sub.5 represents hydrogen, methyl, vinyl, 1-propenyl, 2-methyl-1-propenyl, 2-methoxy-methyl-1-propenyl, 2-methoxycarbonyl-1-propenyl, 1,3-butadienyl, 2-methyl-1,3-butadienyl, 2,2-dichlorovinyl or cyclopentylidenemethyl when R.sub.4 is hydrogen, and R.sub.5 represents methyl when R.sub.4 is methyl; and R.sub.6 and R.sub.7 represent hydrogen or methyl. These novel esters are produced by reacting an alcohol or its halide or arylsulfonate of the formula, ##STR3## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.6 are as defined above, and A is hydroxy, halogen or arylsulfoxy, with a cyclopropanecarboxylic acid of the formula, ##STR4## wherein R.sub.4, R.sub.5 and R.sub.7 are as defined above, or its reactive derivative. These esters are useful as an insecticide harmless to mammals.

Novel cyclopropanecarboxylates

A novel substituted-arylacetic acid ester of the formula, ##STR1## wherein R.sub.1 and R.sub.2 are each hydrogen or a halogen atom, a C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.1 -C.sub.4 alkoxy, cyano, nitro, methylthio, C.sub.1 -C.sub.4 alkanoyl, C.sub.1 -C.sub.4 alkanoyloxy, or C.sub.1 -C.sub.4 alkoxycarbonyl group, or R.sub.1 and R.sub.2, taken together, may form methylenedioxy, a C.sub.3 -C.sub.5 alkylene or butadienylene (--CH.dbd.CH--CH.dbd.CH--) ring; R.sub.3 is a C.sub.2 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, propargyl, C.sub.3 -C.sub.6 cycloalkyl or cyclopropylmethyl group; R.sub.4 is hydrogen or a halogen atom, methyl or ethyl group; R.sub.5 is allyl, propargyl, 3-butenyl, 3-butynyl, phenyl or benzyl group; and A is oxygen or sulfur atom or --CH.dbd.CH-- group, which possesses various useful insecticidal and acaricidal activities and can be prepared by reacting a substituted-arylacetic acid of the formula; ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and A are each as defined above, or a reactive derivative thereof with an alcohol, or halide or sulfonate thereof of the formula, ##STR3## wherein R.sub.4 and R.sub.5 are each as defined above and X is hydroxy group, a halogen atom, alkylsulfonyloxy or arylsulfonyloxy group.

Novel alkynylcyclopropanecarboxylic acid esters represented by the formula, ##STR1## wherein R.sub.1 represents hydrogen, halogen, lower alkyl having up to 5 carbon atoms, lower alkenyl having up to 5 carbon atoms, lower alkynyl having up to 5 carbon atoms, C.sub.1 -C.sub.4 alkoxy C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio C.sub.1 -C.sub.4 alkyl, aryl, aryl C.sub.1 -C.sub.4 alkyl, furyl, substituted furyl, thienyl, substituted thienyl, furfuryl, substituted furfuryl, thenyl, substituted thenyl, cyclo C.sub.3 -C.sub.6 alkyl, substituted cyclo C.sub.3 -C.sub.6 alkyl, cyclo C.sub.3 -C.sub.6 alkenyl or substituted cyclo C.sub.3 -C.sub.6 alkenyl; R.sub.2 and R.sub.3 individually represent hydrogen, halogen, lower alkyl having up to 5 carbon atoms, lower alkenyl having up to 5 carbon atoms, lower alkynyl having up to 5 carbon atoms, aryl, aryl C.sub.1 -C.sub.4 alkyl or may form a carbon-carbon bond; or R.sub.1 and R.sub.3 are bonded to each other at the ends to form a polymethylene chain containing or not containing an oxygen or a sulfur atom, or R.sub.1 and R.sub.2 are bonded to each other at the ends to form a polymethylene chain containing or not containing an oxygen or a sulfur atom; R.sub.4 represents hydrogen or methyl; R.sub.5 represents hydrogen, methyl, vinyl, 1-propenyl, 2-methyl-1-propenyl, 2-methoxymethyl-1-propenyl, 2-methoxycarbonyl-1-propenyl, 2,2-dichlorovinyl or cyclopentyl-idenemethyl when R.sub.4 is hydrogen, and R.sub.5 represents methyl when R.sub.4 is methyl; and R.sub.6 and R.sub.7 represent hydrogen or methyl. These novel esters are produced by reacting an alcohol or its halide or arylsulfonate of the formula, ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.6 are defined above, and A is hydroxy, halogen or arylsulfoxy, with a cyclopropane-carboxylic acid of the formula, ##STR3## wherein R.sub.4, R.sub.5 and R.sub.7 are as defined above, or its reactive derivative. These esters are useful as an insecticide harmless to mammals.

A new pyrethroidal pesticide containing as an active ingredient a pesticidally effective amount of novel cyclopropanecarboxylic acid esters represented by the formula, ##EQU1## wherein R is a hydrogen atom, a halogen atom, a methyl or a methoxy group, and R.sub.1 and R.sub.2 are hydrogen atom, methyl group or a halogen atom, which have a low toxicity to mammals, excellent pesticidal effect on injurious pests in cereal storage, agriculture and forestry and a wide range of uses for prevention of epidemics.

Cyclopropane carboxylic acid esters

A novel cyclopropanecarboxylic acid ester of the formula, ##SPC1## Wherein R.sub.1 is a hydrogen atom, a cyano or ethynyl group, and X is a chlorine, bromine or fluorine atom, which possesses various useful insecticidal and acaricidal activities and can be prepared by reacting a compound of the formula, ##SPC2## Wherein R.sub.1 is as defined above and R.sub.2 is hydroxyl, a halogen atom or an arylsulfoxy group, with a cyclopropanecarboxylic acid of the formula, ##EQU1## wherein X is as defined above, or its reactive derivative.

Cyclopropanecarboxylic acid esters

Thio(dithio)-phosphorate of the formula, ##SPC1## Wherein A represents an alkyl having up to 6 carbon atoms; B represents lower alkyl having up to 4 carbon atoms; Y represents halogen, methoxy or ethoxy; X represents oxygen or sulfur; R.sub.1 represents alkyl having up to 6 carbon atoms, phenyl, phenyl substituted by halogen or phenyl substituted by lower alkyl having up to 4 carbon atoms; R.sub.2 represents hydrogen or alkyl having up to 6 carbon atoms; R.sub.3 represents hydrogen or alkyl having up to 6 carbon atoms; and n represents 0, 1 or 2, which is useful as a pesticide.

Thio(dithio)phosphorates

Compounds of the formula ##EQU1## wherein R is phenyl, .alpha.-naphthyl, substituted phenyl or a group of the formula ##EQU2## R.sub.1 is lower alkyl, R.sub.2 is alkyl, phenyl, aralkyl or substituted phenyl, and R.sub.3 and R.sub.4 are lower alkyl, which compounds are useful as insecticidal, nematocidal and acarididal agents.

Carbamate pesticide

Oximino-phosphorothiolate derivatives represented by the formula, ##EQU1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as hereinafter defined, which are useful as a controlling agent for agricultural pests containing the oximino-phosphorothiolate derivatives as active ingredients, as well as processes for preparing the compounds and the composition are disclosed.

Novel oximino -phosphorothiolate derivatives

A new cyclopropanecarboxylic acid ester represented by the formula, ##SPC1## Wherein R.sub.1 is alkyl having up to four carbon atoms, alkenyl having up to five carbon atoms, cycloalkenyl having up to six carbon atoms, alkenyl having up to five carbon atoms, benzyl, phenoxy or halogen; R.sub.2 and R.sub.3 are hydrogen, halogen or methyl; and any adjacent two of R.sub.1, R.sub.2 and R.sub.3 may combine to form polymethylene, which is useful as insecticides and acaricides having a strong insecticidal activity but a low toxicity to mammals, in agriculture, horticulture as well as public health.

Growing community of inventors

Takarazuka, Japan

Hisami Takeda