Homofarnesals: Female sex attractant pheromone components of the southern cowpea weevil, Callosobruchus chinensis

Journal of Chemical Ecology

Volumn 34, Issue 4, 2008, Pages 467-477

  Shimomura, Kenji ^a   Nojima, Satoshi ^b   Yajima, Shunsuke ^a   Ohsawa, Kanju ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE   (Japan)

^b NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

(2Z,6E) and (2E,6E) 7 Ethyl 3,11 dimethyl 2,6,10 dodecatrienal; Bruchidae; Callosobruchus chinensis; GC EAD; Homofarnesal; Seed beetle; Sex attractant pheromone; Southern cowpea weevil

Indexed keywords

DRUG DERIVATIVE; FARNESAL; FARNESOL; SEX PHEROMONE; UNCLASSIFIED DRUG;

ATTRACTANT; BEETLE; CHROMATOGRAPHY; CROP PEST; INTEGRATED PEST MANAGEMENT; LEGUME; NUCLEAR MAGNETIC RESONANCE; SEX PHEROMONE;

ANIMAL; ARTICLE; FEMALE; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; MALE; METABOLISM; PHYSIOLOGY; WEEVIL;

ANIMALS; CHROMATOGRAPHY, GAS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FARNESOL; FEMALE; HUMANS; MALE; SEX ATTRACTANTS; WEEVILS;

BRUCHINAE; CALLOSOBRUCHUS; CALLOSOBRUCHUS CHINENSIS; CALLOSOBRUCHUS MACULATUS; COLEOPTERA;

EID: 42049091030     PISSN: 00980331     EISSN: 15731561     Source Type: Journal    
DOI: 10.1007/s10886-008-9451-1     Document Type: Article

References (48)

1. Attygalle, A. B. 1998. Microchemical techniques, pp. 207-294, in J. G. Millar, and K. F. Haynes (eds.). Methods in Chemical Ecology: Vol. 1, Chemical Methods. Kluwer, Norwell, MA.
2. Beroza, M., and Bierl, B. A. 1966. Apparatus for ozonolysis of microgram to milligram amounts of compound. Anal. Chem. 38:1976-1977.
3. Beroza, M., and Bierl, B. A. 1967. Rapid determination of olefin position in organic compounds in microgram range by ozonolysis and gas chromatography. Anal. Chem. 39:1131-1135.
4. Borowiec, L. 1987. The genera of seed-beetles (Coleoptera: Bruchidae). Pol. Pis. Entomol. 57:3-207.
5. Burkholder, W. E., and Ma, M. 1985. Pheromones for monitoring and control of stored-product insects. Annu. Rev. Entomol. 30:257-272.
6. Cardé, R. T., and Bell, W. J. (eds.). 1995. Chemical Ecology of Insects. Chapman & Hall, New York.
7. Cork, A., Hall, D. R., Blaney, W. M., and Simmonds, M. S. J. 1991. Identification of a component of the female sex pheromone of Callosobruchus analis (Coleoptera: Bruchidae). Tetrahedron Lett. 32:129-132.
8. Fujii, K., Gatehouse, A. M. R., Johnson, C. D., Mitchell, R., and Yoshida, T. (eds.). 1990. Bruchids and Legumes: Economics, Ecology and Coevolution. Kluwer, Dordrecht.
9. Hariri, G. 1981. Distribution and importance of bruchid attacks on different species of pulses consumed in the Near East, pp. 215-221, in V. Labeyrie (ed.). The Ecology of Bruchids Attacking Legumes (Pulses). Junk, The Hague.
10. Heaps, J. W. (ed.). 2006. Insect Management for Food Storage and Processing, 2nd Edition. AACC International, St. Paul, MN.
11. Honda, H., and Ohsawa, K. 1990. Chemical ecology for stored product insects. J. Pesticide Sci. 15:263-270 (in Japanese with English abstract).
12. Ignacimuthu, S., Wäckers, F. L., and Dorn, S. 2000. The role of chemical cues in host finding and acceptance by Callosobruchus chinensis. Entomol. Exp. Appl. 96:213-219.
13. Imura, O. 1990. Life histories of stored-products insects, pp. 257-270, in K. Fujii, A. M. R. Gatehouse, C. D. Johnson, R. Mitchell, and T. Yoshida (eds.). Bruchids and Legumes: Economics, Ecology and Coevolution. Kluwer, Dordrecht.
14. Labeyrie, V. (ed.). 1981. The Ecology of Bruchids Attacking Legumes (Pulses). Junk, The Hague.
15. Leal, W. S., Kuwahara, Y., Suzuki, T., and Kurosa, K. 1989. The alarm pheromone of the mite Suidasia medanensis Oudemans, 1924 (Acariformes, Suidasiidae). Agric. Biol. Chem. 10:2703-2709.
16. Matsumoto, H., Tebayashi, S., Kuwahara, Y., Matsuyama, S., Suzuki, T., and Fujii, K. 1994. Identification of taxifolin present in the azuki bean as an oviposition stimulant of the azuki bean weevil. J. Pesticide Sci. 19:181-186.
17. Mbata, G. N., Shu, S., and amaswamy, S. B. 2000. Sex pheromones of Callosobruchus subinnotatus and C. maculatus (Coleoptera: Bruchidae): congeneric responses and role of air movement. Bull. Entomol. Res. 90:147-154.
18. Minks, A. K., and Cardé, R. T. 1997. Use of pheromones in direct control, pp. 333-459, in R. T. Cardé, and A. K. Minks (eds.). Insect Pheromone Research, New Directions. Chapman & Hall, New York.
19. Morgan, E. D. 1999. Terpenes, pp. 85-103, in E. D. Morgan (ed.). Biosynthesis in InsectsThe Royal Society of Chemistry. Milton Road, Cambridge.
20. 18-Cecropia juvenile hormone. Tetrahedron 28:3747-3756.
21. Mori, K. 2005. Synthetic examination of incorrectly proposed structures of biomolecules. Chem. Rec. 5:1-16.
22. 18-Cecropia juvenile hormone and its analogues; effect of the terminal alkyl substituents on biological activity. Agri. Biol. Chem. 35:1116-1127.
23. Nojima, S., Kiemle, D. J., Webster, F. X., and Roelofs, W. L. 2004. Submicro scale NMR sample preparation for volatile chemicals. J. Chem. Ecol. 30:2153-2161.
24. Nojima, S., Linn, C. Jr., Morris, B., Zhang, A., and Roelofs, W. L. 2003. Identification of host fruit volatiles from hawthorn (Crataegus spp.) attractive to hawthorn-origin Rhagoletis pomonella flies. J. Chem. Ecol. 29:321-336.
25. Nojima, S., Shimomura, K., Honda, H., Yamamoto, I., and Ohsawa, K. 2007. Contact sex pheromone components of the cowpea weevil, Callosobruchus maculatus. J. Chem. Ecol. 33:923-933.
26. Oshima, K., Honda, H., and Yamamoto, I. 1973. Isolation of an oviposition marker from azuki bean weevil, Callosobruchus chinensis (L.). Agri. Biol. Chem. 37:2679-2680.
27. Phillips, T. W. 1997. Semiochemicals of stored-product insects: research and applications. J. Stored Prod. Res. 33:17-30.
28. Phillips, T. W., Phillips, J. K., Webster, F. X., Tang, R., and Burkholder, W. E. 1996. Identification of sex pheromones from cowpea weevil, Callosobruchus maculatus, and related studies with C. analis (Coleoptera: Bruchidae). J. Chem. Ecol. 22:2233-2249.
29. Rees, D. P. 1995. Coleoptera, pp. 1-40, in B. Subramanyam, and D. W. Hagstrum (eds.). Integrated Management of Insects in Stored Products. Marcel Dekker, Madison Avenue, New York.
30. Sakai, A., Honda, H., Oshima, K., and Yamamoto, I. 1986. Oviposition marking pheromone of two bean weevils, Callosobruchus chinensis and Callosobruchus maculatus. J. Pesticide Sci. 11:163-168.
31. Shinoda, K., and Yoshida, T. 1985. Ecology of azuki weevil in azuki field. I. Emergent prevalence and damage of azuki in azuki field on autumn. Jpn. Appl. Entmol. Zool. 29:14-20 (in Japanese with English summary).
32. Shinoda, K., and Yoshida, T. 1990. Life history of the azuki bean weevil, Callosobruchus chinensis (Coleoptera: Bruchidae), in the field, pp. 149-159, in K. Fujii, A. M. R. Gatehouse, C. D. Johnson, R. Mitchell, and T. Yoshida (eds.). Bruchids and Legumes: Economics, Ecology and Coevolution. Kluwer, Dordrecht.
33. Shinoda, K., Yoshida, T., and Igarashi, H. 1992. Population ecology of the azuki bean beetle, Callosobruchus chinensis (L.), (Coleoptera: Bruchidae) on two wild leguminous hosts, Vigna angularis var. nipponensis and Dunbaria villosa. Appl. Entmol. Zool. 27:311-318.
34. Shinoda, K., Yoshida, T., and Okamoto, T. 1991. Two wild leguminous host plants of the azuki bean weevil, Callosobruchus chinensis (L.) (Coleoptera: Bruchidae). Appl. Entmol. Zool. 26:91-98.
35. Shu, S., Mbata, G. N., Cork, A., and Ramaswamy, S. B. 1998. Female sex pheromone in Callosobruchus subinnotatus (Coleoptera: Bruchidae): Production and male responses. Ann. Entomol. Soc. Am. 91:840-844.
36. Shu, S., Mbata, G. N., Cork, A., and Ramaswamy, S. B. 1999. Sex pheromone of Callosobruchus subinnotatus. J. Chem. Ecol. 25:2715-2727.
37. Siegel, S. 1956. The one-sample case, pp. 35-60, in S. Siegel (ed.). Nonparametric Statistics for the Behavioral Science. McGraw-Hill, New York.
38. Subramanyam, B., and Hagstrum, D. W. (eds.). 2000. Alternatives to Pesticides in Stored-product IPM. Kluwer, Boston, MA.
39. Tanaka, K., Ohsawa, K., Honda, H., and Yamamoto, I. 1981. Copulation release pheromone, Erectin, from the azuki bean weevil (Callosobruchus chinensis L.). J. Pesticide Sci. 6:75-82.
40. Tanaka, K., Ohsawa, K., Honda, H., and Yamamoto, I. 1982. Synthesis of Eectin, a copulation release pheromone of the azuki bean weevil, Callosobruchus chinensis L. J. Pesticide Sci. 7:535-537.
41. Tebayashi, S., Matsuyama, S., Suzuki, T., Kuwahara, Y., Nemoto, T., and Fujii, K. 1995. Quercimertrin: the third oviposition stimulant of the azuki bean weevil from the host azuki bean. J. Pesticide Sci. 20:299-305.
42. Tuda, M., Chou, L.-Y., Niyomdham, C., Buranapanichpan, S., and Tateishi, Y. 2005. Ecological factors associated with pest status in Callosobruchus (Coleoptera: Bruchidae): high host specificity of non-pests to Cajaninae (Fabaceae). J. Stored Pro. Res. 41:31-45.
43. Tuda, M., Rönn, J., Buranapanichpan, S., Wasano, N., and Arnqvist, G. 2006. Evolutionary diversification of the bean beetle genus Callosobruchus (Coleoptera: Bruchidae): traits associated with stored-product pest status. Mol. Ecol. 15:3541-3551.
44. Ueno, T., Kuwahara, Y., Fujii, K., Taper, M. L., Toquenaga, Y., and Suzuki, T. 1990. D-Catechin: an oviposition stimulant of azuki bean weevil Callosobruchus chinensis in the host azuki bean. J. Pesticide Sci. 15:573-578.
45. Watanabe, N. 1990. Diversity in life cycle patterns of bruchids occurring in Japan (Coleoptera: Bruchidae), pp. 141-147, in K. Fujii, A. M. R. Gatehouse, C. D. Johnson, R. Mitchell, and T. Yoshida (eds.). Bruchids and Legumes: Economics, Ecology and Coevolution. Kluwer, Dordrecht.
46. White, N. D. G., and Leesch, J. G. 1996. Chemical Control, pp. 287-330, in B. Subramanyam, and D. W. Hagstrum (eds.). Integrated Management of Insects in Stored Products. Marcel Dekker, Madison Avenue, New York.
47. Yoneda, M., Kaneda, M., and Akiyama, H. 1990. Plant quarantine and fumigation of imported grain legumes in Japan, pp. 115-120, in K. Fujii, A. M. R. Gatehouse, C. D. Johnson, R. Mitchell, and T. Yoshida (eds.). Bruchids and Legumes: Economics, Ecology and Coevolution. Kluwer, Dordrecht.
48. Zagatti, P., Kunesch, G., amiandrasoa, F., Malosse, C., Hall, D. R., Lester, R., and Nesbitt, B. F. 1987. Sex pheromones of rice moth, Corcyra cephalonica Staomtpm I. Identification of male pheromone. J. Chem. Ecol. 13:1561-1573.