Synthesis and miticidal and insecticidal activities of 4-(2-fluoroethyl)-5,6-dihydro-4H-1,3,4-oxadiazines

Dihydrooxadiazines, substituted by a fluoroethyl chain, were prepared by reaction of benzhydrazides with 2 molar equiv of bromofluoroethane. Ten compounds with various substitutions on the phenyl ring were compared with clofentezine, a commercial miticide, for miticidal activity against the egg stage of Tetranychus urticae; the compounds were also compared with thiodicarb, a commercial tobacco budworm insecticide, for insecticidal activity against the egg stage of Heliothis virescens. The mortality data were correlated with the phenyl substitution in the tested compounds. Some halophenyl oxadiazines showed greater miticidal and insecticidal activities than the commercial standards