Isolation, identification, and synthesis of a female sex pheromone of the navel orangeworm, Amyelois transitella (Lepidoptera: Pyralidae)

Abstract

A sex pheromone of the navel orangeworm, Amyelois transitella (Walker), was obtained from ether rinses of the sex pheromone gland of calling females. The pheromone was isolated by means of liquid and gas chromatography and was identified as one of four possible geometrical isomers of 11,13-hexadecadienal by means of spectroscopic and microchemical methods. Synthesis and laboratory bioassay of all four isomers revealed that only the (Z,Z) isomer was biologically active. (Z,Z)-11,13-hexadecadienal elicited quantitatively similar activation and attraction responses by A. transitella males as did the natural product. © 1979 Plenum Publishing Corporation.