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Novel type of sex pheromone structure identified fromStigmella malella (Stainton) (Lepidoptera: Nepticulidae)

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Abstract

Short-chain unsaturated chiral methyl carbinols are identified as a new class of lepidopteran pheromone components. The natural female-produced pheromone of the banded apple pigmyStigmella malella (=Nepticula malella) (Stainton) (Lepidoptera: Nepticulidae) was identified to be a mixture of (S)-(E)-6,8-nonadien-2-ol and (S)-(Z)-6,8-nonadien-2-ol. For monitoring traps, a 10:3E:Z blend at 100–1000 µg is recommended. It is suggested that pheromones with similar structures may be specific to Nepticulidae and other related microlepidopteran families.

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References

  • Aerssens, M.H.P.J., andBrandsma, L. 1984. Regio- and stereo-specific reduction of conjugated and non-conjugated triple bonds by activated zinc powder.J. Chem. Soc. Chem. Commun. 1984:735–736.

    Article  Google Scholar 

  • Andreini, B.P., Benetti, M., Caprita, A., andRossi, R. 1987. Highly stereo- and regio-selective palladium-catalyzed synthesis of (3E,5Z)-, (3E,5E)-, and (3Z,5E)-1,3,5-undecatriene.Tetrahedron 43:4591–4600.

    Article  CAS  Google Scholar 

  • Arn, H., Rauscher, S., andSchmid, A. 1979. Sex attractant formulations and traps for the grape mothEupoecilia ambiguella Hb.Mitt. Schweiz. Entomol. Ges. 52:49–55.

    Google Scholar 

  • Arn, H., Tóth, M., andPriesner, E. 1992. List of Sex Pheromones of Lepidoptera and Related Attractants. 2nd ed. IOBC, Montfavet, 179 pp.

    Google Scholar 

  • Baker, K.V., Brown, J.M., Hughes, N., Skarnoulis, A.J., andSexton, A. 1991. Mechanical activation of magnesium turnings for the preparation of reactive Grignard reagents.J. Org. Chem. 56:698–703.

    Article  CAS  Google Scholar 

  • Balázs, K. 1993. Almalevél-törpemoly—(Nepticula malella Stainton),in T. Jermy, K. Balázs, (eds.). A Növényvédelmi Állattan Kézikönyve 4/A. pp. 38–43. Budapest, Akadémia i Kiadó.

    Google Scholar 

  • Beroza, M. 1975. Microanalytical methodology relating to the identification of insect sex pheromones and related behavior-control chemicals.J. Chromatogr. Sci. 13:314–321.

    PubMed  CAS  Google Scholar 

  • Brandsma, L., 1988. Preparative Acetylenic Chemistry. Elsevier, Amsterdam. 321 pp.

    Google Scholar 

  • Campbell, K.N., andEby, L.T. 1941. The preparation of highercis andtrans olefins.J. Am. Chem. Soc. 63:216–219.

    Article  CAS  Google Scholar 

  • Dehmlow, E.V., andLissel, M. 1979. Anwendungen der Phasentransfer-Kalayse; 9. Neue phasentransfer-katalytische Herstellung von Alkenen aus Alkylhalogeniden.Synthesis 1979:372–374.

    Article  Google Scholar 

  • Francke, W., Franke, S., Tóth, M., Szöcs, G., Guerin, P., andArn, H. 1987. Identification of 5,9-dimethylheptadecane as a sex pheromone of the mothLeucoptera scitella.Naturwissenschaften 74:143–144.

    Article  CAS  Google Scholar 

  • Francke, W., Tóth, M., Szöcs, G., Krieg, W., Ernst, H., andBuschmann, E. 1988. Identifizierung und Synthese von Dimethylalkanen als Sexuallockstoffe weiblicher Miniermotten (Lyonetiidae).Z. Naturforsch. 43c:787–789.

    Google Scholar 

  • Ghirardelli, R.G. 1973. Circular dichroism of a carbocation. (1S,2R)-Dimethyl(2-methylcyclopropyl)carbenium ion.J. Am. Chem. Soc. 95:4987–4990.

    Article  CAS  Google Scholar 

  • Gritter, R.J., andWallace, T.J. 1959. The manganese dioxide oxidation of allylic alcohols.J. Org. Chem. 24:1051–1056.

    Article  CAS  Google Scholar 

  • Hall, D.R., Beevor, P.S., Campion, D.G., Chamberlain, D.J., Cork, A., White, R.D., Almestar, A., andHenneberry, T.J. 1992. Nitrate esters—novel sex pheromone components of the cotton leaf perforator,Bucculatrix thurberiella Busck (Lepidoptera, Lyonetiidae).Tetrahedron Lett. 33:4811–4814.

    Article  CAS  Google Scholar 

  • Hansson, B.S., Szöcs, G., Schmidt, F., Francke, W., Löfstedt, C., andTóth, M. 1990. Electrophysiological and chemical analysis of sex pheromone communication system of the mottled umber,Erannis defoliaria (Lepidoptera: Geometridae).J. Chem. Ecol. 16:1887–1897.

    Article  CAS  Google Scholar 

  • Hübener, A. 1988. Synthese und massenspektroskopische Untersuchung flüchtiger bicyclischer Glycolether. Diplomarbeit, Fachbereich Chemie, Universität Hamburg. 44 pp.

  • Huwyler, S. 1973. Ultramikromethoden: Katalytische Hydrierung.Experientia 29:1310–1311.

    Article  CAS  Google Scholar 

  • Johansson, R., andNielsen, E.S. 1990. Tribus Nepticulini.Fauna Entomol. Scand. 23:111–238 (plates).

    Google Scholar 

  • Johnston, B.D., andSlessor, K.N. 1979. Facile syntheses of the enantiomers of sulcatol.Can. J. Chem. 57:233–235.

    CAS  Google Scholar 

  • König, W.A., Gehrke, B., Icheln, D., Evers, P., Dönnecke, J., andWang, W. 1992. New, selectively substituted cyclodextrins as stationary phases for the analysis of chiral constituents of essential oils.J. High. Resolut. Chromatogr. 15:367–372.

    Article  Google Scholar 

  • McLafferty, F.W., andStauffer, D.B. (eds.), 1989. The Wiley/NBS Registry of Mass Spectral Data. J. Wiley & Sons, New York.

    Google Scholar 

  • Molnárne, J. 1981. ANepticula malella Stt. és aLithocolletis corylifoliella Haw. biológiája, valamint az ellenük való védekezés lehetösége. Növényvédelem 17:231–235.

    Google Scholar 

  • Pietruszka, J., Hochmuth, D.H., Gehrke, B., Ichelin, D., Runge, T., andKönig, W. 1992. Gas chromatographic enantioseparation of allenes.Tetrahedron, Asymmetry 3:661–670.

    CAS  Google Scholar 

  • Réal, P. 1966. Super-famille des Stigmelloidea, pp. 15–24,in A.S. Balachowsky (ed.). Entomologie appliquée à l'agriculture, Vol. 2. Mason et Cie, Paris.

    Google Scholar 

  • Sato, R., Abe, N., Sonnet, P., Sugie, H., andTamaki, Y. 1985. Biological activity of (R)- and (S)-14-methyl-1-octadecene, as the chiral component of the sex pheromone of the peach leafminer moth,Lyonetia clerkella Linné (Lepidoptera: Lyonetiidae).Appl. Entomol. Zool. 20:411–415.

    CAS  Google Scholar 

  • van Nieukerken, E.J. 1986. Systematics and phylogeny of Holarctic genera of Nepticulidae (Lepidoptera, Heteroneura: Monotrysa).Zool. Verh., Leiden 236:1–93.

    Google Scholar 

  • van Nieukerken, E.J., andDop, H. 1987. Antennal sensory structures in Nepticulidae (Lepidoptera) and their phylogenetic implications.Z. Zool. Syst. Evol. Forsch. 25:104–126.

    Article  Google Scholar 

  • van Nieukerken, E.J., andPuplesis, R. 1991. Taxonomy and distribution of theTrifurcula (Glaucolepsis)raikhonae group (Lepidoptera: Nepticulidae).Tijdschr. Entomol. 134:201–210.

    Google Scholar 

  • Wijnberg, J.B.P.A., Wiering, P.G., andSteinberg, H. 1981. Improved synthesis ofN-substituted isopropylideneaziridines.Synthesis 1981:901–903.

    Article  Google Scholar 

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Tóth, M., Szöcs, G., van Nieukerken, E.J. et al. Novel type of sex pheromone structure identified fromStigmella malella (Stainton) (Lepidoptera: Nepticulidae). J Chem Ecol 21, 13–27 (1995). https://doi.org/10.1007/BF02033659

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