Improved Synthesis of (Z,E)-9,11,13-Tetradecatrienal,the Sex Pheromone of the Carob Moth Apomyelois (=Ectomyelois) Ceratoniae (Lepidoptera: Pyralidae)

(Z,E)-9,11,13-Tetradecatrienal is a sex pheromone component emitted by virgin females of the Carob Moth Apomyelois ceratoniae Zeller (Lepidoptera: Pyralidae) which is an important pest of Iranian pomegranate fruits. Chemical control of this pest is not possible and biological methods with pheromones are used. The synthesis of the major component of the sex pheromone was achieved in fewer steps and with lower cost than previously. (Z,E)-9,11,13-Tetradecatrienal was synthesised by four steps with 59% overall yield. The coupling of a conjugated dienynol intermediate from E-1,2-dichloroethylene with vinyl magnesium bromide was achieved in good yield and followed by reduction of dienynol with activated zinc in THF-H₂O and oxidation gave the aldehyde of the sex pheromone.