Synthesis and Electrophysiological Testing of Carbonyl Pheromone Analogues for Carposinid Moths.

Sex pheromone analogues were synthesized and tested on two pest carposinid moth species: the guava moth, Coscinoptycha improbana, and the raspberry bud moth, Heterocrossa rubophaga. The pheromone analogues used for the electroantennogram testing included (Z)-11-methylenenonadec-7-ene, (Z)-nonadec-12-en-9-amine, (Z)-11-methoxynonadec-7-ene, (Z)-1-(octylsulfinyl)-dec-3-ene, and (Z)-nonadec-12-en-9-ol. An imine analogue, N-((Z)-nonadec-12-en-9-ylidene)cyclopropanamine, was also synthesized but was too unstable for testing with the moths. None of the analogue compounds elicited significant responses from the male moth antennae.