Abstract
α- and β-Campholenic nitriles (1a), (2a) were prepared by various methods and converted to campholenic acid chlorides by hydrolysis and chlorination. The chlorocarbonylated campholenes were condensed with pyrrolidine, piperidine, 2-, 3-, or 4-methylpiperidines, and 2, 6- or 3, 5-dimethylpiperidines to obtain amide compounds (3) (16) in 3264 % yields in five steps, the first being imidation of α-pinene or camphor.
Insecticidal activity of amide compounds (3) (16) toward Tyrophagus putrescentiae, Dermatophagoides farinae, Culex pipiens pallens, Musca domestica Linne and Blattella germanica were measured. On filter paper, amide compounds (3) (16) from (1) and (2) showed greater insecticidal activity than N, N-diethyl-m-toluamide for T. putrescentiae and D. farinae.
Toward T. putrescentiae, amide compounds (3) (16) at 1.0 g/m2 expressed insecticidal activity from 75100 %, this range exceeding that of commercial isobornyltiocyano acetic acid. At 1.0 g/m2 for these amide compounds (3) (16), D. farinae was almost eliminated.
