Abstract
Three methylated hydrocarbons, 10,14-dimethyloctadec-1-ene (10Me14Me-1-ene-18Hy = 5Me9Me-17-ene-18Hy), 5,9-dimethyloctadecane (5Me9Me-18Hy), and 5,9-dimethylheptadecane (5Me9Me-17Hy), are synergistic sex pheromone components of the leafminer Lyonetia prunifoliella. Compounds extracted from female pheromone glands were identified by coupled gas chromatographic–electroantennographic detection (GC-EAD), and one compound, 10Me14Me-1-ene-18Hy, also by coupled GC–mass spectrometry. In field trapping experiments, 10Me14Me-1-ene-18Hy, 5Me9Me-18Hy, and 5Me9Me-17Hy singly were unattractive to males but in ternary combination attracted numerous male moths. Attractiveness of the three-component blend significantly exceeded that of two-component blends. No attraction of males to pheromone lures without 10Me14Me-1-ene-18Hy indicates that this compound is essential for pheromone communication of L. prunifoliella. Common C-5 and C-9 methyl branches in lyonetiid pheromone hydrocarbons suggest a common biosynthetic pathway; the presence of 5Me9Me-17Hy and 5Me9Me-18Hy in pheromone blends of L. prunifoliella and Leucoptera malifoliella provides evidence for phylogeny of lyonetiid chemical communication. Determination of the stereoisomeric composition is required to completely describe the pheromone blend of L. prunifoliella and to support the hypothesis of phylogenetically related sex pheromones.
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REFERENCES
ARN, H., STÄDLER, E., and RAUSCHER, S. 1975. The electroantennographic detector—a selective and sensitive tool in the gas chromatographic analysis of insect pheromones. Z. Naturforsch. 30c:722–725.
BROWN, M. W. 1989. Spatial dynamics and sampling of Lyonetia speculella (Lepidoptera: Lyonetiidae), a new leafminer of apple. Environ. Entomol. 18:875–880.
COREY, E. J., and SNIDER, B. B. 1972. A synthesis of (±)-fumagillin. J. Am. Chem. Soc. 1972:2549.
ESMAILI, M. 1971. Four species of leaf miners attacking deciduous fruit trees in Iran's central province. Z. Angew. Entomol. 69:407–415.
FRANCKE, W., FRANKE, S., TÓTH, M., SZÖCS, G., GUERIN, P., and ARN, H. 1987. Identification of 5,9-dimethylheptadecane as a sex pheromone of the moth Leucoptera scitella. Naturwis-senschaften 74:143–144.
FRANCKE, W., TÓTH, M., SZOCS, G., KRIEG, W., ERNST, H., and BUSCHMANN, E. 1988. Identifizierung und Synthese von Dimethylalkanen als Sexuallockstoff weiblicher Miniermotten (Lyonetiidae). Z. Naturforsch. 43c:787–789.
FROST, S. W. 1924. Two little known leaf-miners of apple (Lepid.: Tineidae; Col.: Curculionidae). Entomol. News 35:132–134.
GRIES, G., KING, G. G. S., GRIES, R., WIMALARATNE, P. D. C., GRAY, T. G., SHEPHERD, R. F., LI, J., SLESSOR, K. N., and KHASKIN, G. 1993. 3,13-Dimethylheptadecane: Major sex pheromone component of the western false hemlock looper, Nepytia freemani Munroe (Lepidoptera: Geometridae). J. Chem. Ecol. 19:1501–1510.
GRIES, G., GRIES, R., PEREZ, A. L., OEHLSCHLAGER, A. C., GONZALES, L. M., PIERCE, H. D., JR., ZEBEYOU, M., and KOUAME, B. 1994. Aggregation pheromone of the African rhinoceros beetle, Oryctes monoceros (Olivier) (Coleoptera: Scarabaeidae). Z. Naturforsch. 49c:363–366.
KREMER, W. F. 1963. Major leaf miner species occuring in the South Tirolean fruit-farming region, and their control. Pflanzenschutz-Nachr. 16:1–6.
MAIER, C. T. 1988. A new leafminer, Lyonetia speculella, in Connecticut apple orchards. Rep. Conn. Pomol. Soc. 1987:6–12.
MAIER, C. T. 1995. Hosts and density of Lyonetia spp. (Lepidoptera: Lyonetiidae) mining the foliage of woody ericaceous and rosaceous plants. Ann. Entomol. Soc. Am. 88:739–747.
NARUSE, H. 1978. Defoliation of peach tree caused by the injury of the peach leaf-miner, Lyonetia clerkella L. I. Influence of larval density. Jpn. J. Appl. Entomol. Zool. 22:1–6.
NEWTON, R. F., REYNOLDS, D. P., FINCH, M. A. W., KELLY, D. R., and ROBERTS, S. M. 1979. An excellent reagent for the removal of the t-butyldimethylsilyl protecting group. Tetrahedron Lett. 41:3981–3982.
NONAKA, T., KANEMOTO, S. OSHIMA, K., NOZAKI, H. 1984. Pyridinium flurochromate or benzyl-trimethylammonium chlorochromate for selective oxidation of alcohols. Bull. Chem. Soc. Jpn. 57:2019–2020.
RIBA, M., ROSELL, J. A., EIZAGUIRRE, M., CANELA, R., and GUERRERO, A. 1990. Identification of a minor component of the sex pheromone of Leucoptera malifoliella (Lepidoptera, Lyonetiidae). J. Chem. Ecol. 16:1471–1483.
SATO, R., ABE, N., SONNET, P., SUGIE, H., and TAMAKI, 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. Appl. Entomol. Zool. 20:411–415.
SEKITA, N., and YAMADA, M. 1979. Life history of Lyonetia prunifoliella Hübner subspecies malinella (Matsumura) (Lepidoptera: Lyonetiidae). Appl. Entomol. Zool. 14:285–292.
SCHMITT, J. J., BROWN, M. W., and DAVIS, D. R. 1996. Taxonomy, morphology, and biology of Lyonetia prunifoliella (Lepidoptera: Lyonetiidae), a leafminer of apple. Ann. Entomol. Soc. Am. 89:334–345.
SEPRŌS, I. 1985. Fontosabb Fitofáag Mikrolepidopterák. Aknázómolyok. Mém. Növényvédelmi és Agrokémiai Központja. Budapest.
STILL, W. C., KAHN, M., and MITRA, A., 1978. Rapid chromatographic technique for preparative separations with moderate resolution. J. Org. Chem. 43:2923–2925.
SUGIE, R., and KUMAKURA, M. 1984. Sex pheromone of the peach leafminer moth, Lyonetia clerkella Linné: Isolation and identification. Appl. Entomol. Zool. 19:323–330.
TÓTH, M., HELMCHEN, G., LEIKAUF, U., SZIRAKI, GY., and SZÖCS, G. 1989. Behavioural activity of optical isomers of 5,9-dimethylheptadecane, the sex pheromone of Leucoptera scitella L. (Lepidoptera: Lyonetiidae). J. Chem. Ecol. 15:1534–1543.
VAN DEN DOOL, H., and KRATZ, P. 1963. A generalization of the retention index system including linear temperature programmed gas liquid partion chromatography. J. Chromatogr. 2:463–471.
ZAR, J. H. 1984. Biostatistical Analysis, Prentice-Hall, Englewood Cliffs, New Jersey, 718 pp.
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Gries, R., Gries, G., King, G.G.S. et al. Sex Pheromone Components of the Apple Leafminer, Lyonetia prunifoliella . J Chem Ecol 23, 1119–1130 (1997). https://doi.org/10.1023/B:JOEC.0000006390.43868.3b
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DOI: https://doi.org/10.1023/B:JOEC.0000006390.43868.3b