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

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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.

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References

  • Ando, T. 2011. Internet database: http://www.tuat.ac.jp/~antetsu/lepipherolist.htm

  • Ando, T. and Yamakawa, R. 2011. Analyses of lepidopteran sex pheromones by mass spectrometry. Trends Anal. Chem. 30:990–1002.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • Dunkelblum, E., and Kehat, M. 1987. Sex pheromone precursors in Spodoptera littoralis (Lepidoptera: Noctuidae). Insect Biochem. 17:877–881.

    Article  CAS  Google Scholar 

  • El-sayed, A. M. 2011. Internet database: http://www.pherobase.com/

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • 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 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • 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.

    Article  PubMed  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    PubMed  CAS  Google Scholar 

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • 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.

  • 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.

    Article  PubMed  Google Scholar 

  • Sokal, R. R. and Rohlf, F. J. 1995. Biometry, third edition. W. H. Freeman and Company, New York.

    Google Scholar 

  • 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.

  • 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.

    CAS  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

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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.

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Correspondence to Tetsu Ando.

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Do, N.D., Ohbayashi, K., Naka, H. et al. Identification and Field Evaluation of Sex Pheromone Components of the Pear Barkminer Moth, Spulerina astaurota . J Chem Ecol 37, 1222–1230 (2011). https://doi.org/10.1007/s10886-011-0032-3

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