Selectively fluorinated analogs reveal differential olfactory reception and inactivation of green leaf volatiles in insects.

The role of the alkyl terminus of green leaf volatile (GLV) molecules in olfactory reception and inactivation was examined in three diverse insect species: the beet armyworm,Spodoptera exigua (Lepidoptera); the Colorado potato beetle,Leptinotarsa decemlineata (Coleoptera); and the desert locust,Schistocerca gregaria (Orthoptera), using selectively fluorinated analogs of GLVs and electroantennograms (EAGs). When only the magnitude of the depolarization of the EAG is considered (a measure of reception), the order of effectiveness was 1-hexanol (6:OH)=(Z)-3-6:OH > 5,5,6,6,6-pentafluoro-(Z)-3-6:OH =5,5-difluoro-(Z)-3-6:OH ≫ 5,5,6,6,6-pentafluoro-6: OH. Percent recovery of the EAG (a measure of inactivation) was greater for the pentafluoro-(Z)-3-6: OH analog than for the difluoro-(Z)-3-6: OH analog. Our results show that the alkyl end of GLV molecules plays an important role not only in reception, but also inactivation processes in insect olfaction. Furthermore, specificities of these two processes may differ.