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J Chem Ecol

Title:		"Male-produced aggregation pheromone compounds from the eggplant flea beetle (Epitrix fuscula): identification, synthesis, and field biossays"
Author(s):		Zilkowski BW; Bartelt RJ; Cosse AA; Petroski RJ;
Address:		"USDA Agricultural Research Service, National Center for Agricultural Utilization Research, Crop Bioprotection Research Unit, Peoria, IL 61604, USA. zilkowbw@ncaur.usda.gov"
Journal Title:		J Chem Ecol
Year:		2006
Volume:		32
Issue:		11
Page Number:		2543 - 2558
DOI:		10.1007/s10886-006-9163-3
ISSN/ISBN:		0098-0331 (Print) 0098-0331 (Linking)
Abstract:		"Volatiles from the eggplant flea beetle, Epitrix fuscula Crotch (Coleoptera: Chrysomelidae), feeding on host foliage, were investigated. Six male-specific compounds were detected and were identified through the use of mass spectrometry, nuclear magnetic resonance (NMR) spectrometry, chiral and achiral gas chromatography, high-performance liquid chromatography, electrophysiology (gas chromatography-electroantennography, GC-EAD), and microchemical tests. The two most abundant of the six compounds were (2E,4E,6Z)-2,4,6-nonatrienal (1) and (2E,4E,6E)-2,4,6-nonatrienal (2). The other four compounds, present in minor amounts, were identified as himachalene sesquiterpenes; two of these, 3 and 4, were hydrocarbons and two, 5 and 6, were alcohols. All four sesquiterpenes were previously encountered from male flea beetles of Aphthona spp. and Phyllotreta cruciferae. Synthetic 1 and 2 matched the natural products by GC retention times, mass spectra, and NMR spectra. Sesquiterpenes 3-6 similarly matched synthetic standards and natural samples from the previously studied species in all ways, including chirality. Both natural and synthetic 1 and 2 gave positive GC-EAD responses, as did sesquiterpenes 3, 5, and 6. Field trials were conducted with a mixture of 1 and 2, and the baited traps were significantly more attractive than control traps to both male and female E. fuscula. The E. fuscula pheromone has potential for monitoring or controlling these pests in eggplants"
Keywords:		"Animals Biological Assay Chromatography, Gas Chromatography, High Pressure Liquid Coleoptera/*chemistry Female Magnetic Resonance Spectroscopy Male Mass Spectrometry Pheromones/chemical synthesis/*chemistry/pharmacology;"
Notes:		"MedlineZilkowski, Bruce W Bartelt, Robert J Cosse, Allard A Petroski, Richard J eng 2006/11/01 J Chem Ecol. 2006 Nov; 32(11):2543-58. doi: 10.1007/s10886-006-9163-3"