Biology:Tetradecadienyl acetates

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

  • (Z,E)-3,5-tetradecadienyl acetatePrionoxystus robiniaea mating attractant[2](p41)
  • (E,E)-3,5-tetradecadienyl acetateAccosus centerensis mating attractant[2](p41)
  • (Z,E)-4,8-tetradecadienyl acetateBorkhausenia schefferella mating attractant[2](p41)
  • (Z,Z)-7,11-tetradecadienyl acetateConistra vaccinii mating attractant[2](p41)
  • (Z,E)-9,11-tetradecadienyl acetate (abbr. Z9,E11-14:Ac) — Spodoptera littoralis[3][2](p41) and S. litura[2](p41) mating attractant and mating inhibitor.[2](p41) 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 acetatePlodia interpunctella mating inhibitor[2](p41)
  • (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:

References

  1. 1.0 1.1 1.2 1.3 1.4 1.5 1.6 Burkholder, Wendell E.; Ma, Michael (1985). "Pheromones for Monitoring and Control of Stored-Product Insects". Annual Review of Entomology (Annual Reviews) 30 (1): 257–272. doi:10.1146/annurev.en.30.010185.001353. ISSN 0066-4170. 
  2. 2.00 2.01 2.02 2.03 2.04 2.05 2.06 2.07 2.08 2.09 2.10 2.11 2.12 2.13 Wegler, Richard, ed (7 March 2013) (in en). Herbizide. Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel [Chemistry of Plant Protection and Pesticidal Substances]. 5. Berlin, Heidelberg. pp. XXI+754. doi:10.1007/BF02040406. ISBN 978-3-642-66616-2. OCLC 913650212.  ISBN 978-3642666179.
  3. 3.0 3.1 Raina, Ashok K. (1993). "Neuroendocrine Control of Sex Pheromone Biosynthesis in Lepidoptera". Annual Review of Entomology (Annual Reviews) 38 (1): 329–349. doi:10.1146/annurev.en.38.010193.001553. ISSN 0066-4170. PMID 8424626. 
  4. 4.0 4.1 4.2 4.3 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 (Entomological Society of America (OUP)) 102 (3): 815–835. doi:10.1603/029.102.0301. ISSN 0022-0493. PMID 19610395. 
  5. 5.0 5.1 5.2 Phillips, Thomas W.; Throne, James E. (2010-01-01). "Biorational Approaches to Managing Stored-Product Insects". Annual Review of Entomology (Annual Reviews) 55 (1): 375–397. doi:10.1146/annurev.ento.54.110807.090451. ISSN 0066-4170. PMID 19737083. 
  6. United States Environmental Protection Agency (2006-08-09). "Lepidopteran Pheromones; Exemption from the Requirement of a Tolerance". pp. 45395–45400. http://www.federalregister.gov/documents/2006/08/09/E6-12971/lepidopteran-pheromones-exemption-from-the-requirement-of-a-tolerance.  71 FR 45395. 40 CFR 180. EPA-HQ-OPP-2006-0529FRL-8083-8. Doc. No. E6-12971.