Identification and Synthesis of the Male-Produced Sex Pheromone of the Soldier BeetleChauliognathus fallax(Coleoptera: Cantharidae)

Chauliognathus fallax Germar 1824 (Coleoptera: Cantharidae) occurs in North and South America and Australia.Gas chromatographic (GC) analyses of volatiles released by adults showed the presence of a male specific compound.GC coupled with electroantennographic detection (GC-EAD) showed that this compound is exclusively bioactive on female antennae, suggesting it to be a sex pheromone.GC coupled with mass spectrometry (GC-MS) and Fourier transform infrared spectroscopy (GC-FTIR), as well as dimethyl disulfide (DMDS) derivatization and hydrogenation, suggested the target compound to be (Z)-tricos-11-ene.Unambiguous structural proof was achieved by independent synthesis, whereas the biological significance of the compound as a sex pheromone was confirmed by field bioassays.