Novel cyclopropanecarboxylates

Details Novel cyclopropanecarboxylates Novel cyclopropanecarboxylates

1975-12-02

1978-10-03

Gerstl, Robert

Drug, bio-affecting and body treating compositions

Antigen, epitope, or other immunospecific immunoeffector

Allergen or component thereof

2603322R, 2603405R, 2603458R, 2603474, 260465D, 424282, 424283, 424285, 424304, 424306, 560118, 560124, C07C 6974, A01N 924

Patent

active

041185056

ABSTRACT:
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.

REFERENCES:
patent: 3285950 (1966-11-01), Weber
patent: 3835176 (1974-10-01), Matsuo et al.
patent: 3857858 (1974-12-01), Itaya et al.
patent: 3862174 (1975-01-01), Mizutani et al.

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