Optical Isomers of 3,13-Dimethylheptadecane: Sex Pheromone Components of the Western False Hemlock Looper, Nepytia freemani (Lepidoptera: Geometridae)

Article abstract of DOI:10.1007/BF02033860

(3S,13R)-3,13-Dimethylheptadecane [(3S,13R)-3,13-dime-17Hy] is the major pheromone component of the western false hemlock looper (WFHL), Nepytia freemani. In comparative gas chromatographic-electroantennographic detection (GC-EAD) analyses of stereoselectively synthesized isomers, 1 pg of (3S,13R)-dime-17Hy elicited significantly stronger electrophysiological responses by male WFHL antennae than did 1 pg of separately injected (3R,13R)-, (3R,13S)- or (3S,13S)-3,13-dime-17Hy. In field experiments with individually tested stereoisomers, (3S,13R)-3,13-dime-17Hy was the only stereoisomer to attract males, but the four-stereoisomer blend was 3.6 times more attractive. Quaternary and all binary combinations of (3S,13R)-3,13-dime-17Hy with the other stereoisomers were equally attractive, suggesting that synergistic behavioral activity in WFHL resided with either one of (3R,13R)-, (3R,13S)-, or (3S,13S)-3,13-dime-17Hy. Because optical isomers of (di)methylhydrocarbons do not separate on currently available columns, it remains unknown whether female WFHL also produce a four-stereoisomer pheromone blend. Substitutionality of pheromone stereoisomers without loss of behavioural activity has not previously been reported, but favorably compares with the concept of pheromone redundancy that was first suggested for the multiple pheromone component blend of the cabbage looper moth, Trichoplusia ni.