Synthesis and chemical characterization of hydrocarbons with a 6,9,11-, 3,6,9,11-, or 1,3,6,9-polyene system, pheromone candidates in lepidoptera

Journal of Chemical Ecology

Volumn 34, Issue 8, 2008, Pages 1057-1064

  Yamamoto, Masanobu ^a   Yamakawa, Rei ^a   Oga, Toshiya ^a   Takei, Yousuke ^a   Kinjo, Masakatsu ^b   Ando, Tetsu ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^b UNIVERSITY OF THE RYUKYUS   (Japan)

Author keywords

Diagnostic ion; GC MS analysis; Geometridae; Lepidoptera; Pheromone synthesis; Polyunsaturated hydrocarbon

Indexed keywords

HYDROCARBON; POLYENE; SEX PHEROMONE;

CHEMICAL ANALYSIS; HYDROCARBON; INSECT; SEX PHEROMONE;

ANIMAL; ARTICLE; CHEMISTRY; ISOMERISM; LEPIDOPTERA; MASS FRAGMENTOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ANIMALS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HYDROCARBONS; ISOMERISM; LEPIDOPTERA; MAGNETIC RESONANCE SPECTROSCOPY; POLYENES; SEX ATTRACTANTS;

GEOMETRIDAE; LEPIDOPTERA; NOCTUIDAE;

EID: 48449092943     PISSN: 00980331     EISSN: 15731561     Source Type: Journal    
DOI: 10.1007/s10886-008-9461-z     Document Type: Article

References (23)

1. Ando, T. 2008. Internet database: http://www.tuat.ac.jp/~antetsu/ LepiPheroList.htm.
2. 13C NMR analyses on conjugated dienic pheromones of Lepidoptera Agric. Biol. Chem. 47 2849 2853
3. T. Ando H. Ohsawa T. Ueno H. Kishi Y. Okamura S. Hashimoto 1993 Hydrocarbons with a homoconjugated polyene system and their monoepoxy derivatives: Sex attractants of geometrid and noctuid moths distributed in Japan J. Chem. Ecol. 19 787 798
4. T. Ando H. Kishi N. Akashio X.-R. Qin N. Saito H. Abe S. Hashimoto 1995 Sex attractants of geometrid and noctuid moths: Chemical characterization and field test of monoepoxides of 6,9-dienes and related compounds J. Chem. Ecol. 21 299 311
5. Ando, T., Inomata, S., and Yamamoto, M. 2004. Lepidopteran sex pheromones, pp. 51-96, in S. Schulz (ed.). The Chemistry of Pheromones and Other Semiochemicals I. Topics in Current Chemistry, vol. 239. Springer, Berlin/Heidelberg.
6. H. J. Bestmann T. Brosche K. H. Koschatzky K. Michaelis H. Platz K. Roth J. Süß O. Vostrowsky W. Knauf 1982 Pheromone-XLII. 1,3,6,9-Nonadecatetraen, das Sexualpheromon des Frostspanners Operophtera brumata (Geometridae) Tetrahedron Lett. 23 4007 4010
7. J. Einhorn B. Boniface M. Renou M.-L. Milat 1984 Study on the sex pheromone of Arctia villica L. (Lepidoptera, Arctiidae) C. R. Acad. Sci., Ser. 3 298 573 576
8. El-Sayed, A. M. 2008. Internet database: http://www.pherobase.com/.
9. B. K. Eya T. Otsuka I. Kubo D. L. Wood 1990 Syntheses and NMR analyses of the eight geometrical isomers of 3,6,8-dodecatrien-1-ol, subterranean termite trial pheromone Tetrahedron 46 2695 2706
10. B. Frérot C. Malosse R. D. Chenon P. H. Ducrot A.-H. Cain 1993 Identification of the sex pheromone components in Pareuchaetes pseudoinsulata Rego Barros (Lepidoptera, Arctiidae) C. R. Acad. Sci., Ser. 2 317 1045 1050
11. S. C. Jain D. E. Dussourd W. E. Conner T. Eisner A. Guerrero J. Meinwald 1983 Polyene pheromone components from an arctiid moth (Utetheisa ornatrix): Characterization and synthesis J. Org. Chem. 48 2266 2270
12. Jurenka, R. 2004. Insect pheromone biosynthesis, pp. 97-132, in S. Schulz (ed.). The Chemistry of Pheromones and Other Semiochemicals I. Topics in Current Chemistry, vol. 239. Springer, Berlin/Heidelberg.
13. J. G. Millar 2000 Polyene hydrocarbons and epoxides: A second major class of lepidopteran sex attractant pheromones Annu. Rev. Entomol. 45 575 604
14. T. Nishida L. V. Vang H. Yamazawa R. Yoshida H. Naka K. Tsuchida T. Ando 2003 Synthesis and characterization of hexadecadienyl compounds with a conjugated diene system, sex pheromone of the persimmon fruit moth and related compounds Biosci. Biotechnol. Biochem. 67 822 829
15. Pohnert, G. and Boland, W. 2000. Highly efficient one-pot double-Wittig approach to unsymmetrical (1Z,4Z,7Z)-homoconjugated trienes. Eur. J. Org. Chem. 2000:1821-1826.
16. X.-R. Qin T. Ando M. Yamamoto M. Yamashita K. Kusano H. Abe 1997 Resolution of pheromonal epoxydienes by chiral hplc, stereochemistry of separated enantiomers, and their field evaluation J. Chem. Ecol. 23 1403 1417
17. W. L. Roelofs A. S. Hill C. E. Linn J. Meinwald S. C. Jain H. J. Herbert R. F. Smith 1982 Sex pheromone of the winter moth, a geometrid with unusually low temperature precopulatory responses Science 217 657 659
18. G. Szöcs M. Tóth Z. Kárpáti J. Zhu C. Löfstedt E. Plass W. Francke 2004 Identification of polyenic hydrocarbons from the northern winter moth, Operophtera fagata, and development of a species specific lure for pheromone traps Chemoecology 14 53 58
19. E. W. Underhill J. G. Millar R. A. Ring J. W. Wong D. Barton M. Giblin 1987 Use of a sex attractant and an inhibitor for monitoring winter moth and bruce spanworm populations J. Chem. Ecol. 13 1319 1330
20. S. Wakamura N. Arakaki M. Yamamoto S. Hiradate H. Yasui T. Yasuda T. Ando 2001 Posticlure: A novel trans-epoxide as a sex pheromone component of the tussock moth, Orgyia postica (Walker) Tetrahedron Lett. 42 687 689
21. S. Wakamura N. Arakaki M. Yamamoto S. Hiradate H. Yasui K. Kinjo T. Yasuda H. Yamazawa T. Ando 2005 Sex pheromone and related compounds in the Ishigaki and Okinawa strains of the tussock moth Orgyia postica (Walker) (Lepidoptera: Lymantriidae) Biosci. Biotechnol. Biochem. 69 957 965
22. J. W. Wong P. Palaniswamy E. W. Underhill W. F. Steck M. D. Chisholm 1984 Sex pheromone components of fall cankerworm moth, Alsophila pometaria synthesis and field trapping J. Chem. Ecol. 10 1579 1596
23. J. W. Zhu C. Löfstedt P. Philipp W. Francke T. Tammaru E. Haukioja 1995 A sex pheromone component novel to the Geometridae identified from Epirrita autumnata Entomol. Exp. Appl. 75 159 164