Sex Pheromone of the Pine Sawfly Macrodiprion nemoralis (Hymenoptera: Diprionidae): Identification of (2S,3R.7R,9S)-3,7,9-Trimethyl-2-tridecanol as the Precursor for the Active Pheromone Acetate

摘要

The main component of the sex phero-mone precursor in females of Macrodiprion nemo-ralis was identified as a threo-3,7,9-trimethyl-2-tride-canol isomer, approximately 800 pg per female, by gas chromatography-mass spectrometry. Comparison of mass spectrometric ion chromatograms showed that the natural compound in the female extract has the same retention time and mass spectrum as one of the two synthetic threo peaks. The acetate of the synthetic 16-isomer mixture caught a large number of males in the field, confirming the structure of the active pheromone. Comparison of gas chromatograms of the natural female extract with the eight synthetic threo stereoisomers showed that the pheromone is the (2S,3R,7R,9S)-stereoisomer of 3,7,9-trimethyl-2-tridecyl acetate.