Chemoreceptors in Lepidoptera: Stereochemical Differentiation of Dual Receptors for an Achiral Pheromone

The racemate and optically pure enantiomers of 9-(2-cyclopenten-1yl)nonyl acetate have been synthesized and shown to mimic certain biological properties of (Z)-11-tetradecenyl acetate. European corn borers and red-banded leaf rollers respond differently to the racemate and to the enantiomers in precopulatory behavior bioassay. The responses demonstrate the presence of two stereospecific chemoreceptors, show the chiral character of these receptors, and define the conformation of carbon atoms 10 to 14 of (Z)-11-tetradecenyl acetate in these receptors.