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(S)-2-Acetoxy-5-Undecanone, Female Sex Pheromone of the Raspberry Cane Midge, Resseliella theobaldi (Barnes)

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The raspberry cane midge, Resseliella theobaldi, is a widespread pest of cultivated red raspberry in Europe. Pheromone-baited traps could provide a much-needed, accurate means to monitor the pest. Volatiles collected separately from virgin female and male midges were analyzed by gas chromatography (GC) coupled to mass spectrometry (MS) to reveal four female-specific components. In analyses by GC coupled to electroantennographic (EAG) recording from the antennae of a male midge, at least three of these components elicited responses. Based on its GC retention indices and mass spectrum, we propose that the major component is 2-acetoxy-5-undecanone and confirm this by synthesis of the racemic compound in seven steps and 63% yield from 4-pentenoic acid. The three minor components were each present at approximately 30% of the major component and were identified as 2-undecanone, (S)-2-acetoxyundecane, and (S)-2-undecanol by comparison of GC retention times and mass spectra with those of synthetic standards. GC analyses of the female-produced volatiles on an enantioselective column showed that only one enantiomer of 2-acetoxy-5-undecanone was present, and this was found to be the S-enantiomer by hydrolytic kinetic resolution of an epoxide intermediate in the synthesis and also by enantioselective hydrolysis of the racemic acetate with a lipase enzyme. The two enantiomers were also separated by high-performance liquid chromatography on an enantioselective column for field tests. In two field trapping tests, (S)-2-acetoxy-5-undecanone was highly attractive to male R. theobaldi; the R-enantiomer was not attractive. The racemic compound was just as attractive as the S-enantiomer, and addition of the three minor components in racemic form at two different loads did not affect catches. The pheromone could be dispensed from both rubber septa and polyethylene vials for at least 1 month under field conditions, but the former was preferred as it gave more uniform release. 2-Acetoxy-5-undecanone belongs to a new group of pheromone structures in the Cecidomyiidae, most others being mono- or diesters.

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  • Anonymous. 2003a. Pesticides Residues Committee. Pesticides Monitoring Report. Second quarter April–June 2003. PRC_2003_Q2_Reporta(2).pdf, 233 pp.

  • Anonymous. 2003b. Pesticides residues Committee. Pesticides Monitoringreport. Fourth quarter October-December 2003. Assets/PRC/PRC_2003_Q4_report.pdf, 424 pp.

  • Choi, M.-Y., Khaskin, G., Gries, R., Gries, G., Roitberg, B. D., Raworth, D. A., Kim, D.-H., and Bennett, R. G. 2004. (2R,7S)-Diacetoxytridecane: sex pheromone of the aphidophagous gall midge, Aphidoletes aphidimyza. J. Chem. Ecol. 30:659–670.

    Article  PubMed  CAS  Google Scholar 

  • Cork, A., Beevor, P. S., Gough, J. E., and Hall, D. R. 1990. Gas chromatography linked to electroantennography: a versatile technique for identifying insect semiochemicals, pp. 271–279, in A. R. McCaffery, and I. D. Wilson (eds.). Chromatography and Isolation of Insect Hormones and Pheromones. Plenum Press, London.

    Google Scholar 

  • Cross, J. V., and Hall, D. R. 2005. Pheromones. PCT/GB2005/002504.

  • Cross, J. V., and Hall, D. R. 2009. Exploitation of the sex pheromone of apple leaf midge Dasineura mali Kieffer (Diptera: Cecidomyiidae): Part 1. Development of lure and trap. Crop Protection. doi:10.1016/j.cropro.2008.09.008.

  • Cross, J., Baroffio, C., Grassi, A., Hall, D., Labanowska, B., Milenković, S., Nilsson, T., Shternshis, M., Tornéus, C., Trandem, N., and Vétek, G. 2009a. Monitoring raspberry cane midge, Resseliella theobaldi, with sex pheromone traps: results from 2006. IOBC/WPRS Bull. (in press).

  • Cross, J. V., Hall, D. R., Shaw, P., and Anfora, G. 2009b. Exploitation of the sex pheromone of apple leaf midge Dasineura mali Kieffer (Diptera: Cecidomyiidae): Part 2. Use of sex pheromone traps for pest monitoring. Crop Protection. doi:10.1016/j.cropro.2008.09.004.

  • Foster, S. P., Harris, M. O., and Millar, J. G. 1991. Identification of the sex pheromone of the Hessian fly, Mayetiola destructor (Say). Naturwissenschaften 78:130–131.

    Article  CAS  Google Scholar 

  • Gordon, S. C., Barrie, I. A., and Woodford, J. A. T. 1989. Predicting spring oviposition by raspberry cane midge from accumulated derived soil temperatures. Ann. Appl. Biol. 114:419–427.

    Article  Google Scholar 

  • Gries, R., Gries, G., Khaskin, G., King, G. G. S., Olfert, O., Kaminski, L., Lamb, R. G., and Bennett, R. 2000. Sex pheromone of the orange wheat blossom midge, Sitodiplosis mosellana. Naturwissenschaften 87:450–454.

    Article  PubMed  CAS  Google Scholar 

  • Gries, R., Khaskin, G., Gries, G., Bennett, R. G., King, G. G. S., Morewood, P., Slessor, K. N., and Morewood, W. D. 2002. (Z,Z)-4,7-Tridecadien-(S)-2-yl acetate: sex pheromone of the Douglas-fir cone gall midge, Contarinia oregonensis. J. Chem. Ecol. 28:2283–2297.

    Article  PubMed  CAS  Google Scholar 

  • Gries, R., Khaskin, G., Daroogheh, H., Mart, C., Karadag, S., Kubilay Er, M., Britton, R., and Gries, G. 2006. (2S,12Z)-2-Acetoxy-12-heptadecene: major sex pheromone component of pistachio twig borer, Kermania pistaciella. J. Chem. Ecol. 32:2667–2677.

    Article  PubMed  CAS  Google Scholar 

  • Hall, D., Cross, J., Farman, D., Innocenzi, P., Ando, T., and Yamamoto, M. 2005. Sex pheromones of apple leaf curling midge, Dasineura mali, and raspberry cane midge, Resseliella theobaldi: a new class of pheromone structures. Abstracts of 21st Annual Meeting of International Society of Chemical Ecology, Washington, p. 46.

  • Hall, D. R., Cork, A., Phythian, S. J., Chittamuru, S., Jayarama, Venkatesha, M. G., Sreedharan, K., Seetharama, H. G., Vinod Kumar, P. K., and Naidu, R. 2006. Identification of components of male-produced pheromone of coffee white stemborer, Xylotrechus quadripes Chevrolat (Coleoptera: Cerambycidae). J. Chem. Ecol. 32:213–237.

  • Harris, M. O., and Foster, S. P. 1999. Gall midges, pp. 27–50, in J. Hardie, and A. K. Minks (eds.). Pheromones of Non-lepidopteran Insects Associated with Agricultural Plants. CABI Publishing, Wallingford, UK.

    Google Scholar 

  • Hillbur, Y., Anderson, P., Arn, H., Bengtsson, M., Löfqvist, J., Biddle, A. J., Smitt, O., Högberg, H.-E., Plass, E., Franke, S., and Francke, W. 1999. Identification of sex pheromone components of the pea midge, Contarinia pisi (Diptera: Cecidomyiidae). Naturwissenschaften 86:292–294.

    Article  CAS  Google Scholar 

  • Hillbur, Y., El-Sayed, A., Bengtsson, M., Löfqvist, J., Biddle, A., Plass, E., and Francke, W. 2000. Laboratory and field study of the attraction of male pea midges, Contarinia pisi, to synthetic sex pheromone components. J. Chem. Ecol. 26:1941–1952.

    Article  CAS  Google Scholar 

  • Hillbur, Y., Bengtsson, M., Löfqvist, J., Biddle, A., Pillon, O., Plass, E., Francke, W., and Hallberg, E. 2001. A chiral sex pheromone system in the pea midge, Contarinia pisi. J. Chem. Ecol. 27:1391–1407.

    Article  PubMed  CAS  Google Scholar 

  • Hillbur, Y., Celander, M., Baur, R., Rauscher, S., Haftmann, J., Franke, S., and Francke, W. 2005. Identification of the sex pheromone of the swede midge, Contarinia nasturtii. J. Chem. Ecol. 31:1807–1828.

    Article  PubMed  CAS  Google Scholar 

  • Jorgenson, M. 1970. Preparation of ketones from the reaction of organolithium reagents with carboxylic acids. Organic Reactions 18:1–97.

    CAS  Google Scholar 

  • Lacey, E. S., Moreira, J. A., Millar, J. G., Ray, A. M., and Hanks, L. M. 2007. Male-produced aggregation pheromone of the cerambycid beetle Neoclytus mucronatus mucronatus. Entomol. Exp. Appl. 122:171–179.

    Article  CAS  Google Scholar 

  • Qin, X.-R., Ando, T., Yamamoto, M., Yamashita, M., Kusano, K., and Abe, H. 1997. Resolution of pheromonal epoxydienes by chiral HPLC, stereochemistry of separated enantiomers, and their field evaluation. J. Chem. Ecol. 23:1403–1417.

    Article  CAS  Google Scholar 

  • Suckling, D. M., Walker, J. T. S., Shaw, P. W., Manning, L.-A., Lo, P., Wallis, R., Bell, V., Sandanayaka, W. R. M., Hall, D. R., Cross, J. V., and El-Sayed, A. M. 2007. Trapping Dasinuera mali (Diptera: Cecidomyiidae) in apples. J. Econ. Entomol. 100:745–751.

    Article  PubMed  Google Scholar 

  • Tokunaga, M., Larow, J. F., Kakiuchi, F., and Jacobsen, E. N. 1997. Asymmetric catalysis with water: efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis. Science 277:936–938.

    Article  PubMed  CAS  Google Scholar 

  • Xiao, L., and Kitazume, T. 1997. Optically active propargylic and allylic alcohols with a difluoromethyl group at the terminal carbon. Tetrahedron Asymm. 21:3597–3601.

    Article  Google Scholar 

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This work was funded by the UK Department for the Environment, Food and Rural Affairs (Projects HH3124SSF and HL0175) and the Horticultural Development Council (Project SF74). We thank Adrian Harris, Antonia Zurbuchen, and Esther Debón Verdū for assistance with the field tests.

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Correspondence to David R. Hall.

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Hall, D.R., Farman, D.I., Cross, J.V. et al. (S)-2-Acetoxy-5-Undecanone, Female Sex Pheromone of the Raspberry Cane Midge, Resseliella theobaldi (Barnes). J Chem Ecol 35, 230–242 (2009).

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