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Journal of Chemical Ecology

, Volume 37, Issue 11, pp 1222–1230 | Cite as

Identification and Field Evaluation of Sex Pheromone Components of the Pear Barkminer Moth, Spulerina astaurota

  • Nguyen Duc Do
  • Kanako Ohbayashi
  • Hideshi Naka
  • Ken Nakada
  • Tetsu Ando
Article

Abstract

The pear barkminer moth, Spulerina astaurota Meyrick (Gracillariidae: Gracillariinae), is a harmful pest of the Asian-pear tree. Pheromone components of the female were analyzed by gas chromatography (GC) with an electroantennographic (EAG) detector and GC coupled with mass spectrometry. The analyses of a crude pheromone extract and those of a fractionated extract on a Florisil column indicated three EAG-active components, tetradecadien-1-ol, its acetate, and an aldehyde derivative. Characteristic fragment ions in the mass spectra of the dienyl compounds and derivatives with 4-methyl-1,2,4-triazoline-3,5-dione revealed double bonds at the 9- and 11-positions. By comparing the chromatographic behaviors to those of four authentic geometrical isomers, which were synthesized by three different routes starting from 1,8-octanediol or 1,9-nonanediol, the configuration of each natural component was assigned to be 9Z,11Z; i.e., it was concluded that the S. astaurota females secreted (9Z,11Z)-9,11-tetradecadien-1-ol (Z9,Z11-14:OH) as a main pheromone component, and the acetate and aldehyde derivatives (Z9,Z11-14:OAc and Z9,Z11-14:Ald) as minor components. This identification was confirmed by a field evaluation of the synthetic pheromone. While the male moths could be attracted to a lure baited with Z9,Z11-14:OH alone, Z9,Z11-14:OAc showed a strong synergistic effect on the attraction. Among the lures tested, the mixture of alcohol and acetate in a ratio of 7:3 exhibited the strongest attraction. Addition of Z9,Z11-14:Ald in the mixture did not significantly increase the number of males attracted. Furthermore, the field test indicated that some contamination of a geometrical isomer of the alcohol did not impair the activity of the binary mixture with the 9Z,11Z configuration.

Key Words

Female sex pheromone Lepidoptera Gracillariidae Gracillariinae (9Z,11Z)-9,11-Tetradecadien-1-ol 9,11-Dienyl compounds Conjugated dienes Male attraction Asian pear Insect pest monitoring 

Notes

Acknowledgements

We thank the Asian-pear growers, especially T. Ikuhashi, Y. Kaigo, Y. Nakahara, H. Ohta, S. Okabe, K. Takeuchi, and I. Tokuyama, who participated in this research and contributed their farms and time to the effort. We are grateful to T. Ishiko and S. Toita of the Tottori Prefectural Agriculture and Forest Research Institute. We also thank Drs. F. Tamura, A. Itai and M. Azuma for offering important information, and Ms. A. Oda and students of the Laboratory of Applied Entomology in Faculty of Agriculture at Tottori University for their help with field experiments and rearing insects.

Supplementary material

10886_2011_32_MOESM1_ESM.doc (104 kb)
ESM 1 (DOC 104 kb)

References

  1. Ando, T. 2011. Internet database: http://www.tuat.ac.jp/~antetsu/lepipherolist.htm
  2. Ando, T. and Yamakawa, R. 2011. Analyses of lepidopteran sex pheromones by mass spectrometry. Trends Anal. Chem. 30:990–1002.CrossRefGoogle Scholar
  3. Ando, T., Ogura, Y., and Uchiyama, M. 1988. Mass spectra of lepidopterous sex pheromones with a conjugated diene system. Agric. Biol. Chem. 52:1415–1423.CrossRefGoogle Scholar
  4. Beevor, P. S., Cork, A., Hall, D. R., Nesbitt, B. F., Day, R. K., and Mumford, J. D. 1986. Components of female sex pheromone of cocoa pod borer moth, Conopomorpha cramerella. J. Chem. Ecol. 12:1–23.CrossRefGoogle Scholar
  5. Dunkelblum, E., and Kehat, M. 1987. Sex pheromone precursors in Spodoptera littoralis (Lepidoptera: Noctuidae). Insect Biochem. 17:877–881.CrossRefGoogle Scholar
  6. El-sayed, A. M. 2011. Internet database: http://www.pherobase.com/
  7. Ferrao, P., Gries, G., Wimalaratne, P. D. C., Maier, C. T., Gries, R., Slessor, K. N., and Li, J. 1998. Sex pheromone of apple blotch leafminer, Phyllonorycter crataegella, and its effect on P. mespilella pheromone communication. J. Chem. Ecol. 24:2059–2078.CrossRefGoogle Scholar
  8. Foster, S. P., and Roelofs, W. L. 1990. Biosynthesis of a monoene and a conjugated diene sex pheromone component of the lightbrown apple moth by Δ11 desaturation. Experientia 46:269–273.CrossRefGoogle Scholar
  9. Inomata, S., Watanabe, A., Nomura, M., and Ando, T. 2005. Mating communication systems of four Plusiinae species distributed in Japan: Identification of the sex pheromones and field evaluation. J. Chem. Ecol. 31:1429–1442.PubMedCrossRefGoogle Scholar
  10. Kuroko, H. 1982. Gracillariidae, pp. 176–202, in H. Inoue, S. Sugi, H. Kuroko, S. Moriuti, A. Kawabe and M. Owada. Moths of Japan. Kodansha Co. Ltd., Tokyo, Japan. (in Japanese)Google Scholar
  11. Lapointe, S. L., Hall, D. G., Murata, Y., Parka-Pedrazzoli, A. L., Bento, J. M. S., Vilela, E. F., and Leal, W. S. 2006. Field evaluation of a synthetic female sex pheromone for the leafmining moth Phyllocnistis citrella (Lepidoptera: Gracillariidae) in Florida citrus. Fla. Entomol. 89:274–276.CrossRefGoogle Scholar
  12. Leal, W. S., Parra-Pedrazzoli, A. L., Cossé, A. A., Murata, Y., Bento, J. M. S., and Vilela, E. F. 2006. Identification, synthesis, and field evaluation of the sex pheromone from the citrus leafminer, Phyllocnistis citrella. J. Chem. Ecol. 32:155–168.PubMedCrossRefGoogle Scholar
  13. Löfstedt, C., Zhu, J., Kozlov, M. V., Buda, V., Jirle, E. V., Hellqvist, S., Löfqvist, J., Plass, E., Franke, S., and Francke, W. 2004. Identification of the sex pheromone of the currant shoot borer Lampronia capitella. J. Chem. Ecol. 30:643–658.PubMedCrossRefGoogle Scholar
  14. Mafi, S. A., Vang, L. V., Nakata, Y., Ohbayashi, N., Yamamoto, M., and Ando, T. 2005. Identification of the sex pheromone of the citrus leafminer (Phyllocnistis citrella Stainton, Lepidoptera: Gracillariidae) with a trial of control by the communication disruption method. J. Pestic. Sci. 30:361–367.CrossRefGoogle Scholar
  15. Martinez, T., Fabriás, G., and Camps, F. 1990. Sex pheromone biosynthetic pathway in Spodoptera littoralis and its activation by neurohormone. J. Biol. Chem. 265:1381–1387.PubMedGoogle Scholar
  16. Moreira, J. A., Mcelfresh, J. S., and Millar, J. G. 2006. Identification, synthesis, and field testing of the sex pheromone of the citrus leafminer, Phyllocnistis citrella. J. Chem. Ecol. 32:169–194.PubMedCrossRefGoogle Scholar
  17. Mori, K. 2009. New synthesis of (11Z,13Z)-11,13-hexadecadienal, the female sex pheromone of the navel orangeworm. Biosci. Biotechnol. Biochem. 73:2727–2730.PubMedCrossRefGoogle Scholar
  18. Mori, K., and Brevet, J.-L. 1991. Pheromone synthesis; CXXXIII. Synthesis of both the enantiomers of (3Z,9Z)-cis-6,7-epoxy-3,9-nonadecadiene, a pheromone component of Erannis defoliaria. Synthesis 1125–1129.Google Scholar
  19. Mozûraitis, R., Bûda, V., Liblikas, I., Unelius, C. R., and Borg-Karlson, A.-K. 2002. Parthenogenesis, calling behavior, and insect-released volatiles of leafminer moth Phyllonorycter emberizaepenella. J. Chem. Ecol. 28:1191–1208.PubMedCrossRefGoogle Scholar
  20. Sokal, R. R. and Rohlf, F. J. 1995. Biometry, third edition. W. H. Freeman and Company, New York.Google Scholar
  21. Sonogashira, K., Tohda, Y., and Hagihara, N. 1975. A convenient synthesis of acetylenes: Catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines. Tetrahedron Lett. 4467–4470.Google Scholar
  22. Sugie, H., Tamaki, Y., Kawasaki, K., Wakou, M., Oku, T., Hirano, C., and Horiike, M. 1986. Sex pheromone of the apple leafminer moth, Phyllonorycter ringoniella (Matsumura) (Lepidoptera: Gracillariidae): Activity of geometrical isomers of tetradecadienyl acetates. Appl. Entomol. Zool. 21:578–581.Google Scholar
  23. Svatoš, A., Kalinová, B., Hoskovee, M., Kindl, J., Hovorka, O., and Hrdy, I. 1999. Identification of a new lepidopteran sex pheromone in picogram quantities using an antennal biodetector: (8E,10Z)-Tetradeca-8,10-dienal from Cameraria ohridella. Tetrahedron Lett. 40:7011–7014.CrossRefGoogle Scholar
  24. Ujiye, T., Wakou, M., Oku, T., Homma, K., Kawasaki, K., Tamaki, Y., and Sugie, H. 1986. Sex pheromone of the apple leafminer moth (Phyllonorycter ringoniella): Isolation and identification of the pheromone. Jpn. J. Appl. Entomol. Zool. 30:268–271.CrossRefGoogle Scholar
  25. Young, D. C., Vouros, P., and Holick, M. F. 1990. Gas chromatography-mass spectrometry of conjugated dienes by derivatization with 4-methyl-l,2,4-triazoline-3,5-dione. J. Chromatogr. 522:295–302.PubMedCrossRefGoogle Scholar
  26. Zhu, J., Ryrholm, N., Ljungberg, H., Hansson, B. S., Hall, D., Reed, D., and Löfstedt, C. 1996. Olefinic acetates, Δ-9,11-14:OAc and Δ-7,9-12:OAc used as sex pheromone components in three geometrid moths, Idaea aversata, I. straminata, and I. biselata (Geometridae, Lepidoptera). J. Chem. Ecol. 22:1505–1526.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Nguyen Duc Do
    • 1
  • Kanako Ohbayashi
    • 2
  • Hideshi Naka
    • 2
  • Ken Nakada
    • 3
  • Tetsu Ando
    • 1
  1. 1.Graduate School of Bio-Applications and Systems EngineeringTokyo University of Agriculture and TechnologyKoganeiJapan
  2. 2.Laboratory of Applied Entomology, Faculty of AgricultureTottori UniversityTottoriJapan
  3. 3.Horticultural Research CenterTottori Prefectural Agriculture and Forest Research InstituteHokueiJapan

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