Tetradecadienyl acetates

Various tetradecadienyl acetate compounds serve as insect mating pheromones especially among^[1] the Pyralidae. These include:

• (Z,E)-3,5-tetradecadienyl acetate — Prionoxystus robiniaea mating attractant^[2]: 41
• (E,E)-3,5-tetradecadienyl acetate — Accosus centerensis mating attractant^[2]: 41
• (Z,E)-4,8-tetradecadienyl acetate — Borkhausenia schefferella mating attractant^[2]: 41
• (Z,Z)-7,11-tetradecadienyl acetate — Conistra vaccinii mating attractant^[2]: 41
• (Z,E)-9,11-tetradecadienyl acetate (abbr. Z9,E11-14:Ac) — Spodoptera littoralis^[3][2]: 41 and S. litura^[2]: 41 mating attractant and mating inhibitor.^[2]: 41 Female pheromone, lures males.^[4] Used by McVeigh and Bettany 1986 and Downham et al., 1995 over the course of three years in a 99:1 with (E,E)-10,12-tetradecadienyl acetate.^[4] Although they achieved good mating disruption this did not result in lower egg mass or population.^[4] The results of Campion et al., 1980 suggest that may be due to the need for other, minor female volatiles.^[4] Martinez et al., 1993 study control of its synthesis in S. littoralis by hormones, finding that the reduction step may be controlled by pheromone biosynthesis activating neuropeptide.^[3]
• (Z,Z)-9,12-tetradecadienyl acetate — Plodia interpunctella mating inhibitor^[2]: 41
• (Z,E)-9,12-tetradecadienyl acetate (abbr. Z9,E12-14:Ac)^[5] — In 2006 the United States Environmental Protection Agency granted^[6] an exemption to permit use without regard to the residue on resulting food.^[5] This is thought to be the first registration for indoor use in the United States of any sex pheromone to disrupt mating.^[5] Produced by species:
  • Adoxophyes fasciata synergistic attractant^[2]: 41
  • Anagasta kuehniella^[1] mating attractant produced by both male and female^[2]: 41
  • Cadra cautella^[1] female-produced mating attractant and mating inhibitor^[2]: 41 (found by Kuwahara et al., 1971)^[1]
  • C. figulilella^[1] female-produced mating attractant^[2]
  • Elasmopalpus lignosellus mating disruptor^[2]
  • Ephestia elutella^[1] mating attractant^[2]
  • Plodia interpunctella (also by Kuwahara 1971)^[1]