Synthetic pyrethrin analogues and insecticidal compositions containing them

摘要

The invention relates to compounds of the general formula in which Z represents an aryl, alkenyl or carboalkoxy alkenyl group, R3 represents a halogen atom or an alkyl, alkenyl or alkadienyl group and R1, R2, R4 and R5 which may be the sam or different, each represent hydrogen or halogen atoms or alkyl groups, not more than two of R1, R2, R4 and R5 representing hydrogen atoms when R3 represents a halogen atom or alkyl group. Compounds claimed per se are 4-allylbenzyl (/sB) - cis - trans - chrysanthemate, 4 - allyl - benzyl (/sB) - trans - chrysanthemate, 4 - allyl - benzyl (/sB) - trans - pyrethrate, 4 - allyl - benzyl (/sB) - cis - trans - 3 - phenyl - 2,2 - dimethyl cyclopropane carboxylate, 4-vinyl-benzyl (/sB)-cis-trans-chrysanthemate, 4-vinyl-benzyl (/sB)-trans-pyrethrate, 4-crotyl-benzyl (/sB) - cis - trans - chrysanthemate, 4 - propenylbenzyl (/sB) - cis - trans - chrysanthemate, 4 - (21-methallyl) - benzyl (/sB) - cis - trans - chrysanthemate, 4-allyl-2-methyl-benzyl (/sB)-cis-transchrysanthemate, 4 - allyl - 2,5 - dimethyl - benzyl (/sB) - cis - trans - chrysanthemate, 4 - allyl - tetramethyl - benzyl (/sB) - cis - trans - chrysanthemate, 2,4,6 - trimethylbenzyl (/sB) - cis - trans - chrysanthemate, 2,4,6 - trimethyl - benzyl (/sB) - 3 - phenyl - 2,2 - dimethylcyclopropane carboxylate, pentamethyl-benzyl (/sB)-cis-trans-chrysanthemate, 4 - allyl - 2,6 - dimethyl - benzyl(/sB) - cis - trans - chrysanthemate, 4 - allyl - 2,6 - dimethyl - benzyl (/sB) - trans-chrysanthemate, 4-(21-methallyl)-2,6-dimethyl benzyl (/sB) - cis - trans - chrysanthemate, pentafluoro-benzyl (/sB) - cis - trans - chrysanthemate, 4 - trans - sorbyl - benzyl (/sB) - cis - trans - chrysanthemate. The compounds may be prepared by reacting the cyclopropane carboxylic acid or acid derivative thereof of the general formula with a substituted benzyl derivative of the general formula in which COP and Q represent functional groups which react together to form an ester linkage, for example respectively a carboxylic acid halide and a hydroxy group, a carboxylic acid silver salt group and a halogen atom, and a carboxylic acid triethylamine salt group and a halogen atom. Many examples are given.ALSO:Insecticidal compositions comprise an inert diluent or carrier and as active ingredient a compound of the general formula in which Z represents an aryl, alkenyl or carboalkoxyalkenyl group, R3 represents a halogen atom or an alkyl group and R1, R2, R4 and R5 which may be the same or different, each represent a hydrogen or halogen atom or an alkyl, alkenyl or alkadienyl group, not more than two of R1, R2, R4 and R5 representing hydrogen atoms when R3 represents a halogen atom or alkyl group. Specified active ingredients are 4-allyl-benzyl (+)-trans-chrysanthemate 4-allyl-benzyl (/sB)-cis-trans-chrysanthemate 4-(2/sv-methallyl)benzyl (/sB)-cis-trans-chrysanthemate, 4-allyl-2-methyl-benzyl (/sB)-cis-trans-chrysanthemate, 4-vinyl (/sB)-cis-trans-chrysanthemate, 4-crotyl (/sB)-cis-trans-chrysanthemate, 2,4,6-trimethylbenzyl (/sB)-cis-trans-chrysanthemate, 2,4-dimethyl-benzyl (/sB)-cis-trans chrysanthemate pentamethylbenzyl (/sB)-cis-trans chrysanthemate, 4-allyl-2,6-dimethyl-benzyl(+) - trans - chrysanthemate, 4-(2/sv-methallyl)-2,6-dimethyl-benzyl (/sB)-cis-trans-chrysanthemate. The active ingredients may be deposited on paper bags and sacks to give long lasting protection against insect attack to the contents of the paper bags and sacks. They may also be added to water supplies to kill larval and adult stages of insects, e.g. mosquitoes. The compounds may also be used to kill ticks and mites on cattle and sheep; be added to chicken feed to suppress roundworm and be added to cattle food to control face-fly larv .