Male-produced aggregation pheromone compounds from the eggplant flea beetle (Epitrix fuscula): Identification, synthesis, and field biossays

Journal of Chemical Ecology

Volumn 32, Issue 11, 2006, Pages 2543-2558

  Zilkowski, Bruce W ^a   Bartelt, Robert J ^a   Cossé, Allard A ^a   Petroski, Richard J ^a  

^a NATIONAL CENTER FOR AGRICULTURAL UTILIZATION RESEARCH   (United States)

Author keywords

(2E,4E,6E) 2,4,6 nonatrienal; (2E,4E,6Z) 2,4,6 nonatrienal; Aggregation pheromone; Chrysomelidae; Coleoptera; Epitrix fuscula; Field trials; Flea beetles; Himachalene; Sesquiterpene

Indexed keywords

PHEROMONE;

AGGREGATION PHEROMONE; BEETLE; BIOASSAY; FEEDING; FOLIAGE; HOST PLANT; IDENTIFICATION METHOD; VOLATILE SUBSTANCE;

ANIMAL; ARTICLE; BEETLE; BIOASSAY; CHEMISTRY; FEMALE; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MALE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ANIMALS; BEETLES; BIOLOGICAL ASSAY; CHROMATOGRAPHY, GAS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FEMALE; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MASS SPECTROMETRY; PHEROMONES;

ALTICINI; APHTHONA; BRASSICACEAE; CHRYSOMELIDAE; COLEOPTERA; EPITRIX FUSCULA; PHYLLOTRETA CRUCIFERAE; SIPHONAPTERA (FLEAS); SOLANUM MELONGENA;

EID: 33751083310     PISSN: 00980331     EISSN: 15731561     Source Type: Journal    
DOI: 10.1007/s10886-006-9163-3     Document Type: Article

References (37)

1. ANDERSEN, C. R. 2000. Eggplant. Home Gardening Series. University of Arkansas Cooperative Extension Service. FSA 6010 http://www.uaex.edu/ Other_Areas/publications/PDF/FSA-6010.pdf.
2. BARTELT, R. J., WEISLEDER, D., and PLATTNER, R. D. 1990. Synthesis of the nitidulid beetle pheromones: alkyl-branched tetraene hydrocarbons. J. Agric. Food Chem. 38:2192-2196.
3. BARTELT, R. J., COSSÉ, A. A., ZILKOWSKI, B. W., WEISLEDER, D., and MOMANY, F. A. 2001. Male-specific sesquiterpenes from Phyllotreta and Aphthona flea beetles. J. Chem. Ecol. 27:2397-2423.
4. BARTELT, R. J., WEISLEDER, D., and MOMANY, F. A. 2003. Total synthesis of himachalene sesquiterpenes of Aphthona and Phyllotreta flea beetles. Synthesis 117-123.
5. BARTELT, R. J., COSSÉ, A. A., ZILKOWSKI, B. W., WEISLEDER, D., GRODE, S. H., WIEDENMANN, R. N., and POST, S. L. 2006. Dimethylfuran-lactone pheromone from males of Galerucella calmariensis and Galerucella pusilla. J. Chem. Ecol. 32:693-712.
6. BOUTAGY, J. and THOMAS, R. 1974. Olefin synthesis with organic phosphonate carbanions. Chem. Rev. 74:87-99.
7. BUTTERY, R. G. 1975. Nona-2,4,6-trienal, an unusual component of blended dry beans. J. Agric. Food Chem. 23:1003-1004.
8. CAPINERA, J. L. 2001. Handbook of Vegetable Pests. Academic Press, San Diego, CA.
9. COSSÉ, A. A. and BARTELT, R. J. 2000. Male-produced aggregation pheromone of Colopterus truncates: Structure, electrophysiological and behavioral activity. J. Chem. Ecol. 26:1735-1748.
10. COSSÉ, A. A., BARTELT, R. J., ZILKOWSKI, B. W., BEAN, D. W., and PETROSKI, R. J. 2005. The aggregation pheromone of Diorhabda elongata, a biological control agent of saltcedar (Tamarix spp.): Identification of two behaviorally active components. J. Chem. Ecol. 31:657-670.
11. DELAHAUT, K. 2001. Flea Beetles. University of Wisconsin Garden Facts. University of Wisconsin Extension X1022. 〈http://www.uwex.edu/ces/wihort/ gardenfacts/x1022.pdf〉.
12. GÖTZ-SCHMIDT, E. and SCHREIER, P. 1986. Neutral volatiles from blended endive (Cichorium endivia, L.). J. Agric. Food Chem. 34:212-215.
13. + onto silica gel in HPLC columns for the separation of geometrical isomers. J. Liq. Chromatogr. 3:1129-1135.
14. KREFT, A. 1977. Reduction of hindered allylic esters - a cautionary note. Tetrahedron Lett. 23:1959-1960.
15. KUEPPER, G. 2003. Flea Beetle: Organic Control Options. Appropriate Technology Transfer for Rural Areas. March: 1-6 〈http://attra.ncat.org/ attra-pub/fleabeetle.html〉.
16. MCLEOD, P., DIAZ, F. J., and JOHNSON, D. T. 2002. Toxicity, persistence, and efficacy of Spinosad, Chlorfenapyr, and Thiamethoxam on eggplant when applied against the eggplant flea beetle (Coleoptera: Chrysomelidae). J. Econ. Entomol. 95:331-335.
17. MEHTA, G. and SINGH, B. P. 1977. Terpenes and related systems. 16. Fate of representative bicyclic sesquiterpenes in strong acid medium: A general rearrangement of hydroazulene sesquiterpenes to decalin types. J. Org. Chem. 42:632-638.
18. MILLER, A. E. G., BISS, J. W., and SCHWARTZMAN, L. H. 1959. Reductions with dialkylaluminum hydrides. J. Org. Chem. 24:627-630.
19. MORI, K. 2005. Synthesis of (R)-ar-turmerone and its conversion to (R)-ar-himachalene, a pheromone component of the flea beetle: (R)-ar-himachalene is dextrorotatory in hexane, while levorotatory in chloroform. Tetrahedron: Asymmetry 16:685-692.
20. MUTO, S., BANDO, M., and MORI, K. 2004. Synthesis and stereochemistry of the four himachalene-type sesquiterpenes isolated from the flea beetle (Aphthona flava) as pheromone candidates. Eur. J. Org. Chem. 2004:1946-1952.
21. NÄF, R. and VELLUZ, A. 2000. The volatile constituents of extracts of cooked spinach leaves (Spinacia oleracea L.). Flavour Fragr. J. 15:329-334.
22. PATTON, T. W., DIVELY, G. P., and MILLER, A. K. 2003. Evaluation of organic insecticides for the control of flea beetles on eggplant, 2002. Arthropod Management Test 28: E30. 〈http://www.entsoc.org/Protected/AMT/ AMT28/Text/E30.htm〉.
23. PENG, C. and WEISS, M. J. 1992. Evidence of an aggregation pheromone in the flea beetle, Phyllotreta cruciferae (Goeze) (Coleoptera: Chrysomelidae). J. Chem. Ecol. 18:875-884.
24. PENG, C., BARTELT, R. J., and WEISS, M. J. 1999. Male crucifer flea beetles produce an aggregation pheromone. Physiol. Entomol. 24:98-99.
25. PETROSKI, R. J. 2003. Straightforward preparation of (2E,4Z)-2,4- heptadien-1-ol and (2E,4Z)-2,4-heptadienal. Synth. Commun. 33:3233-3241.
26. PETROSKI, R. J. and WEISLEDER D. 2001. Improved Horner-Wadsworth-Emmons preparation of α-methyl- or α-ethyl-α,β-unsaturated esters from aldehydes. Synth. Commun. 31:89-95.
27. PIVNICK, K. A., LAMB, R. J., and REED, D. 1992. Response of flea beetles, Phyllotreta spp., to mustard oils and nitriles in field trapping experiments. J. Chem. Ecol. 18:863-873.
28. SCHUH, C. and SCHIEBERLE, P. 2005. Characterization of (E,E,Z)-2,4,6,-nonatrienal as a character impact aroma compound of oat flakes. J. Agric. Food Chem. 53:8699-8705.
29. SCHUH, C. and SCHIEBERLE, P. 2006. Characterization of the key aroma compounds in the beverage prepared from Darjeeling black tea: Quantitative differences between tea leaves and infusion. J. Agric. Food Chem. 54:916-924.
30. SMITH, E. H. 1983. Revision of the Genus Phyllotreta Chevrolat of America North of Mexico: Part I. The maculate species (Coleoptera: Chrysomelidae, Alticinae). Fieldiana, Zool. 28:1-168.
31. SORENSEN, K. A. and BAKER, J. R. (eds.). 1994. Insect and related pests of vegetables. N. Carolina Cooperative Extension Service. AG295 〈http://ipm.ncsu.edu/AG295/html/eggplant_flea_beetle.htm〉.
32. SOROKA, J. J., BARTELT, R. J., ZILKOWSKI, B. W., and COSSÉ, A. A. 2005. Responses of the flea beetle Phyllotreta cruciferae to synthetic aggregation pheromone components and host plant volatiles in field trials. J. Chem. Ecol. 31:1829-1843.
33. TÓTH, M., CSONKA, E., BARTELT, R. J., COSSÉ, A. A., ZILKOWSKI, B. W., MUTO, S., and MORI, K. 2005. Pheromonal activity of compounds identified from male Phyllotreta cruciferae: Field tests of racemic mixtures, pure enantiomers, and combinations with allyl isothiocyanate. J. Chem. Ecol. 31:1-16.
34. VINCENT, C. and STEWART, R. K. 1984. Effect of allyl isothiocyanate on field behavior of crucifer-feeding flea beetles (Coleoptera: Chrysomelidae). J. Chem. Ecol. 10:33-39.
35. WILLIAMS, M. A. and FLEMING, I. 1980. Spectroscopic Methods in Organic Chemistry, 3rd ed. McGraw-Hill, London.
36. WILEY. 1995. Wiley. Spectral Library, [CD-ROM], 6th ed. John Wiley & Sons, New York.
37. ZHANG, Z.-Q. and MCEVOY, P. B. 1994. Attraction of Longitarsus jacobaeae males to cues associated with conspecific females (Coleoptera: Chrysomelidae). Environ. Entomol. 23:732-737.