Sumitomo Chemical Company, Limited

Norbushige Itaya

Masachika Hirano

Nobuo Ohno

Takashi Matsuo

Toshio Mizutani

Yoshitoshi Okuno

Hisami Takeda

Shigeyoshi Kitamura

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

Growing community of inventors

Nishinomiya, Japan

Norbushige Itaya