(1S)-1-Ethyl-2-Methylpropyl 3,13-Dimethylpentadecanoate: Major Sex Pheromone Component of Paulownia Bagworm, Clania variegata
- 199 Downloads
The Paulownia bagworm, Clania variegata Snell. (Lepidoptera: Psychidae), is one of the most significant forest defoliators in China. In gas chromatographic (GC)–electroantennographic detection analyses of pheromone gland extracts of female C. variegata on three GC columns (DB-5, DB-23, DB-210), two compounds (A and B) elicited strong responses from male antennae. The more abundant component B was isolated by high-performance liquid chromatography and identified as 1-ethyl-2-methylpropyl 3,13-dimethylpentadecanoate by transesterification, GC-mass spectrometry (MS), and comparison of its spectral and GC retention characteristics with those of synthetic compounds. In field trapping experiments in China, racemic and (1S)-1-ethyl-2-methylpropyl 3,13-dimethylpentadecanoate [but not the (1R)-stereoisomer] attracted male C. variegata. The absolute configuration of B (a molecule with three chiral centers) and the structure of component A remain to be determined.
KeywordsPaulownia bagworm Clania variegata Psychidae Sex pheromone 1-Ethyl-2-methylpropyl 3,13-dimethylpentadecanoate
We thank Keith N. Slessor and Jianxiong Li for provision of laboratory space and contributions at a very early stage of this project, Sadao Wakamura for a reference sample, Eberhard Kiehlmann for constructive comments and critical review of the manuscript, Mei-Keng Yang for elemental analyses, Derek Vance Steel, Sharon Oliver, and Renee Picard for word processing, and Bob Birtch for graphical illustrations. The research was supported by grants from the Natural Science Foundation of China (Nos. 333917041 and 39670613), a grant from the China Ministry of Forestry (948 project, 2005-4-19), a Discovery grant from the Natural Sciences and Engineering Research Council of Canada (NSERC) to G.G., and by a NSERC-Industrial Research Chair to G.G. with Phero Tech Inc., SC Johnson Canada, and Global Forest as industrial sponsors.
- 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.Google Scholar
- Arn, H., Tóth, M., and Priesner, E. 1992. List of Sex Pheromones of Lepidoptera and Related Attractants. 2nd ed. Int. Org. Biol. Control Monfavet, p. 179.Google Scholar
- El-Sayed, A. M. 2005. The Pherobase: Database of Insect Pheromones and Semiochemicals. <http://www.pherobase.com>.
- Georgoulis, C., Smadja, W., and Ville, G. 1984. Convenient deuterium labeling on a gas–liquid chromatography column. Preparative-scale formation of α,β-unsaturated deuterated alcohols. Bull. Soc. Chim. Fr. 7–8(Part 2):269–270.Google Scholar
- Grundon, M. F., Khan, W. A., Boyd, O. R., and Jackson, W. R. 1971. Lithium alkyl(hydro)dipinan-3a-yl borates. New reagents for asymmetric reduction in ketones. J. Chem. Soc. (C):2557–2559.Google Scholar
- Jennings, W., and Shibamoto, T. 1980. Qualitative Analysis of Flavor and Fragrance Volatiles by Glass Capillary Gas Chromatography. Academic Press, New York, p. 472.Google Scholar
- Leonhardt, B. A., Mastro, V. C., Schwartz, M., Tang, J. D., Charlton, R. E., Pellegrinitoole, A., Warthen, J. D., Schwalbe, C. P., and Cardé, R. T. 1991. Identification of sex pheromone of browntail moth, Euproctis chrysorrhoea (L.) (Lepidoptera, Lymantriidae). J. Chem. Ecol. 17:897–910.CrossRefGoogle Scholar
- Mclafferty, F. W., and Tureèek, F. 1993. Interpretation of Mass Spectra. 4th ed. University Science Books, Sausalito, CA, p. 371.Google Scholar
- SAS/STAT. 1988. User's Guide, Release 6.03 Edition. SAS Institute, Cary, NC, p. 1028.Google Scholar
- Tan, Z., Lin, K., Wu, Y., Zhou, W., Wu, G., Tian, H., and Sheng, H. 1987 (in Chinese). Structural study on the sex pheromone of big bagworm (Clania variegata Snellen). Kexue Tongbao 22:1742–1746.Google Scholar
- Trivedi, S. V., and Mamdapur, V. R. 1986. Synthesis of 14-methylpentadecan-3-one. Indian J. Chem. 25B:176–177.Google Scholar
- Van den Dool, H. and Kratz, P. D. 1963. A generalization of the retention index system including linear temperature programmed gas–liquid partition chromatography. J. Chromatogr. 2:463–471.Google Scholar
- Wakamura, S., Yasuda, T., Ichikawa, A., Fukomoto, T., and Mochizuki, F. 1994. Sex attractant pheromone of the tea tussock moth, Euproctis pseudoconspersa (Strand) (Lepidoptera: Lymantriidae): identification and field attraction. Appl. Entomol. Zool. 29:403–411.Google Scholar
- Zar, J. H. 1984. Biostatistical Analysis. Prentice-Hall, Englewood Cliffs, NJ, p. 718.Google Scholar
- Zhang, Z.-Z. 1997. Forest Entomology. China Forestry Publishing House, Beijing.Google Scholar
- Zhao, B. G. 1981. Studies on the glands and release mechanism of the female sex pheromone in Clania variegata Snell. I. Localization of the site that releases sex pheromone in Clania variegata Snell (English abstract). J. Nanjing Technol. Coll. For. Prod. 4:97–102.Google Scholar
- Zhao, B. G. 1984. Studies on the glands and release mechanism of the female sex pheromone in Clania variegata Snell. III. A preliminary report on the morphology, histology, and cytology of the female sex pheromone glands (English abstract). J. Nanjing Inst. For. 4:137.Google Scholar