Syntheses and Determination of Absolute Configurations and Biological Activities of the Enantiomers of the Longtailed Mealybug Pheromone

Preparation and assignment of absolute configurations to both enantiomers of the sex pheromone of the longtailed mealybug, an irregular monoterpenoid with extraordinary biological activity, has been completed. Comparison of the biological activities of both enantiomers and the racemate in field trials showed that the (S)-(+)-enantiomer was highly attractive to male mealybugs, strongly suggesting that female longtailed mealybugs produce this enantiomer. The (R)-(−)-enantiomer was benign, being neither attractive nor inhibitory.