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]

References

1. Burkholder, Wendell E.; Ma, Michael (1985). "Pheromones for Monitoring and Control of Stored-Product Insects". Annual Review of Entomology. 30 (1). Annual Reviews: 257–272. doi:10.1146/annurev.en.30.010185.001353. ISSN 0066-4170. S2CID 85656973.
2. Wegler, Richard, ed. (7 March 2013). Herbizide [Herbicides]. Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel [Chemistry of Plant Protection and Pesticidal Substances]. Vol. 5. Berlin, Heidelberg. pp. XXI+754. doi:10.1007/BF02040406. ISBN 978-3-642-66616-2. OCLC 913650212. S2CID 27560418. ISBN 978-3642666179.
3. Raina, Ashok K. (1993). "Neuroendocrine Control of Sex Pheromone Biosynthesis in Lepidoptera". Annual Review of Entomology. 38 (1). Annual Reviews: 329–349. doi:10.1146/annurev.en.38.010193.001553. ISSN 0066-4170. PMID 8424626.
4. El-Sayed, A. M.; Suckling, D. M.; Byers, J. A.; Jang, E. B.; Wearing, C. H. (2009-06-01). "Potential of "Lure and Kill" in Long-Term Pest Management and Eradication of Invasive Species". Journal of Economic Entomology. 102 (3). Entomological Society of America (OUP): 815–835. doi:10.1603/029.102.0301. ISSN 0022-0493. PMID 19610395. S2CID 16623066.
5. Phillips, Thomas W.; Throne, James E. (2010-01-01). "Biorational Approaches to Managing Stored-Product Insects". Annual Review of Entomology. 55 (1). Annual Reviews: 375–397. doi:10.1146/annurev.ento.54.110807.090451. hdl:2097/12419. ISSN 0066-4170. PMID 19737083.
6. United States Environmental Protection Agency (2006-08-09). "Lepidopteran Pheromones; Exemption from the Requirement of a Tolerance". Federal Register. pp. 45395–45400. Retrieved 2022-04-20. 71 FR 45395. 40 CFR 180. EPA-HQ-OPP-2006-0529FRL-8083-8. Doc. No. E6-12971.