MOTH RESPONSES TO SELECTIVELY FLUORINATED SEX-PHEROMONE ANALOGS

Partially fluorinated analogs of the European corn borer (Ostrinia nub ilalis) female sex pheromone, 11-tetradecenyl acetate (97:3 Z: E), hav ing mono- and trifluorosubstitutions at the terminal carbon of the phe romone chain, mimicked the biological activity of the pheromone, while analogs with fluorine at either side of the double bond and a pentafl uoro analog were essentially inactive. Comparison of the pheromonal ac tivity of these analogs with the previously reported activity of simil arly fluorinated pheromones in five other species of moths revealed an unpredictable relationship between fluorine substitution pattern and pheromone-mimicking activity. Fluorine substitution pat terns that ren dered pheromonal analogs biologically inactive in the European corn bo rer had no detrimental influence upon pheromonal activity in other spe cies and the converse was also true. This is evidence that the relativ e importance of electronic qualities of sites within a pheromone molec ule differ from species to species. Furthermore, it indicates that the biochemical components (pheromone receptor proteins, binding proteins , and enzymes) that make up moth olfactory chemosensory systems must a lso vary structurally from species to species, despite the fact that t hey are involved in olfactory sensing of compounds having very similar chemical structure.