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J Chem Ecol

Title:		"(2E,6Z,9Z)-2,6,9-Pentadecatrienal as a Male-Produced Aggregation-Sex Pheromone of the Cerambycid Beetle Elaphidion mucronatum"
Author(s):		Millar JG; Mitchell RF; Meier LR; Johnson TD; Mongold-Diers JA; Hanks LM;
Address:		"Department of Entomology, University of California, Riverside, CA, 92521, USA. millar@ucr.edu. Department of Entomology, University of Illinois at Urbana-Champaign, Urbana, IL, 61801, USA. Department of Biology, University of Wisconsin Oshkosh, Oshkosh, WI, 54901, USA"
Journal Title:		J Chem Ecol
Year:		2017
Volume:		20171118
Issue:		11-Dec
Page Number:		1056 - 1065
DOI:		10.1007/s10886-017-0905-1
ISSN/ISBN:		1573-1561 (Electronic) 0098-0331 (Linking)
Abstract:		"An increasing body of evidence suggests that the volatile pheromones of cerambycid beetles are much more diverse in structure than previously hypothesized. Here, we describe the identification, synthesis, and field testing of (2E,6Z,9Z)-2,6,9-pentadecatrienal as a male-produced aggregation-sex pheromone of the cerambycid Elaphidion mucronatum (Say) (subfamily Cerambycinae, tribe Elaphidiini). This novel structure is unlike any previously described cerambycid pheromone, and in field bioassays attracted only this species. Males produced about 9 mug of pheromone per 24 h period, and, in field trials, lures loaded with 10, 25, and 100 mg of synthetic pheromone attracted beetles of both sexes, whereas lures loaded with 1 mg of pheromone or less were not significantly attractive. Other typical cerambycine pheromones such as 3-hydroxy-2-hexanone, syn-2,3-hexanediol, and anti-2,3-hexanediol were not attractive to E. mucronatum, and when combined with (2E,6Z,9Z)-2,6,9-pentadecatrienal, the former two compounds appeared to inhibit attraction. Unexpectedly, adults of the cerambycine Xylotrechus colonus (F.) were attracted in significant numbers to a blend of 3-hydroxyhexan-2-one and (2E,6Z,9Z)-2,6,9-pentadecatrienal, even though there is no evidence that this species produces the latter compound. From timed pheromone trap catches, adults of E. mucronatum were determined to be active from dusk until shortly after midnight"
Keywords:		"Aldehydes/chemical synthesis/*chemistry/pharmacology Animals Behavior, Animal/drug effects Coleoptera/drug effects/*physiology Female Male Sex Attractants/*chemistry/pharmacology Stereoisomerism Antagonism Attractant Dose response Interspecific cross-attr;"
Notes:		"MedlineMillar, Jocelyn G Mitchell, Robert F Meier, Linnea R Johnson, Todd D Mongold-Diers, Judith A Hanks, Lawrence M eng 2015-67013-23173/National Institute of Food and Agriculture/ 2017/11/21 J Chem Ecol. 2017 Dec; 43(11-12):1056-1065. doi: 10.1007/s10886-017-0905-1. Epub 2017 Nov 18"