Sumitomo Chemical Company, Limited

Shigeyoshi Kitamura

Takashi Matsuo

Nobuo Ohno

Toshio Mizutani

Nobushige Itaya

Masachika Hirano

Yositosi Okuno

Shunichi Hashimoto

Katsuzo Kamoshita

Hiroshi Noguchi

Yoshitoshi Okuno

Hisami Takeda

Akihiko Mine

Fujio Masuko

Takeaki Umemura

Yoshitaka Ume

Kazuhiko Fujiyoshi

Shinji Nakai

Norbushige Itaya

A herbicidal composition which comprises as an active ingredient a m-phenoxybenzamide compound of the formula: ##STR1## wherein X, which may be the same or different, is a halogen atom or a lower alkyl or lower alkoxy group, n is zero or an integer of 1 to 5 and R is a group of the formula: ##STR2## (in which R.sub.1 is a hydrogen atom or a lower alkyl or lower alkenyl group and R.sub.2 is a lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, lower cycloalkyl, lower haloalkyl, lower alkoxy-substituted lower alkyl, lower cyanoalkyl, lower alkylamino-substituted lower alkyl or benzyl group) or an ethylenimino, pyrrolidino, dimethylpyrrolidino, piperidino, methylpiperidino, hexamethylenimino, morpholino or dimethylmorpholino group.

M-Phenoxybenzamide derivatives

A compound of the formula, ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are respectively hydrogen atom or methyl, R.sub.5 is a member of ##STR2## wherein R.sub.6 is hydrogen atom or methyl, R.sub.7 is alkenyl, alkadienyl, alkynyl or benzyl, R.sub.8 is hydrogen atom, ethynyl or cyano, R.sub.9 is hydrogen atom, a halogen atom or alkyl, R.sub.10 is a halogen atom, alkyl, alkenyl, alkynyl, benzyl, thenyl, furylmethyl, phenoxy, substituted phenoxy of phenylthio, or R.sub.9 and R.sub.10 are bonded at the ends to form polymethylene chain containing or not containing oxygen or sulfur atom, Y is oxygen atom, sulfur atom or --CH.dbd.CH--, n is 1 or 2, Z is phthalimido, thiophthalimido, di- or tetra-hydrophthalimido or dialkylmaleimido, R.sub.11 is phenyl, thienyl or furyl and X is a halogen atom, which is useful as an active ingredient of insecticides.

Novel alkadienylcyclopropanecarboxylates

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

M-phenoxybenzamide derivatives

A compound of the formula, ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are respectively hydrogen atom or methyl, R.sub.5 is a member of ##STR2## wherein R.sub.6 is hydrogen atom or methyl, R.sub.7 is alkenyl, alkadienyl, alkynyl or benzyl, R.sub.8 is hydrogen atom, ethynyl or cyano, R.sub.9 is hydrogen atom, a halogen atom or alkyl, R.sub.10 is a halogen atom, alkyl, alkenyl, alkynyl, benzyl, thenyl, furylmethyl, phenoxy, substituted phenoxy or phenylthio, or R.sub.9 and R.sub.10 are bonded at the ends to form polymethylene chain containing or not containing oxygen or sulfur atom, Y is oxygen atom, sulfur atom or --CH.dbd.CH--, n is 1 or 2, Z is phthalimido, thiophthalimido, di- or tetra-hydrophthalimido or dialkylmaleimido, R.sub.11 is phenyl, thienyl or furyl and X is a halogen atom, which is useful as an active ingredient of insecticides.

Insecticidal alkadienylcyclopropanecarboxylates

m-Phenoxybenzamide derivatives

A process for producing 3-methyl-2-(4-halophenyl)butyronitrile, which is an important intermediate for the production of insecticides, in a high yield and a high purity even on a commercial scale comprising reacting a p-halophenylacetonitrile having a p-halobenzyl alcohol content of not more than 1.0 % by weight, with an isopropyl halide having an isopropyl alcohol content of not more than 1.0 % by weight.

Process for producing a 3-methyl-2-(4-halophenyl)butyronitrile

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

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 compound of the formula, ##SPC1## Wherein R.sub.1 is a C.sub.1.sub.-6 alkyl, a C.sub.2.sub.-6 alkenyl, a C.sub.3.sub.-6 alkynyl, a C.sub.3.sub.-6 cycloalkyl, benzyl, thienyl or a group of ##SPC2## (R.sub.4 is hydrogen, halogen, a C.sub.1.sub.-4 alkyl or methylenedioxy, and n is an integer of 1 to 5), R.sub.2 is a C.sub.1.sub.-6 alkyl, a C.sub.3.sub.-6 alkenyl or a C.sub.3.sub.-6 alkynyl, R.sub.3 is a C.sub.1.sub.-6 alkyl, a C.sub.3.sub.-6 alkenyl or a C.sub.3.sub.-6 alkynyl, (provided that R.sub.2 is a C.sub.3.sub.-6 alkynyl when R.sub.3 is a C.sub.1.sub.-6 alkyl), and A is a group of --COOR.sub.3 or --CH.sub.2 OR.sub.3, provided that R.sub.1 is a C.sub.1.sub.-6 alkyl, a C.sub.2.sub.-6 alkenyl, a C.sub.3.sub.-6 alkynyl, a C.sub.3.sub.-6 cycloalkyl or benzyl when A is a group of --CH.sub.2 OR.sub.3 (R.sub.3 is as defined above), and R.sub.3 is a C.sub.4.sub.-6 alkenyl or a C.sub.4.sub.-6 alkynyl when R.sub.1 is a group of ##SPC3## (R.sub.4 and n are as defined above) and A is a group of --COOR.sub.3, which is useful as synergist for insecticides, especially for a cyclopropane-carboxylate or a carbamate type insecticide.

Phenylacetic acid derivatives

A compound of the formula, ##EQU1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are respectively hydrogen atom or methyl, R.sub.5 is a member of ##SPC1## --CH.sub.2 Z or ##EQU2## wherein R.sub.6 is hydrogen atom or methyl, R.sub.7 is alkenyl, alkadienyl, alkynyl or benzyl, R.sub.8 is hydrogen atom, ethynyl or cyano, R.sub.9 is hydrogen atom, a halogen atom or alkyl, R.sub.10 is a halogen atom, alkyl, alkenyl, alkynyl, benzyl, thenyl, furylmethyl, phenoxy, substituted phenoxy or phenylthio, or R.sub.9 and R.sub.10 are bonded at the ends to form polymethylene chain containing or not containing oxygen or sulfur atom, Y is oxygen atom, sulfur atom or --CH=CH--, n is 1 or 2, Z is phthalimido, thiophthalimido, di- or tetra-hydrophthalimido or dialkylmaleimido, R.sub.11 is phenyl, thienyl or furyl and X is a halogen atom, which is useful as an active ingredient of insecticides.

Growing community of inventors

Toyonaka, Japan

Shigeyoshi Kitamura