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J Chem Ecol

Title:		Limoniic Acid - Major Component of the Sex Pheromones of the Click Beetles Limonius canus and L. californicus
Author(s):		Gries R; Alamsetti SK; van Herk WG; Catton HA; Meers S; Lemke E; Gries G;
Address:		"Department of Biological Sciences, Simon Fraser University, Burnaby, British Columbia, V5A 1S6, Canada. Agassiz Research and Development Centre, Agriculture and Agri-Food Canada, Agassiz, British Columbia, V0M 1A0, Canada. Lethbridge Research and Development Centre, Agriculture and Agri-Food Canada, Lethbridge, Alberta, T1J 4B1, Canada. Mayland Consulting, Calgary, Alberta, T2E 4V5, Canada. Department of Biological Sciences, Simon Fraser University, Burnaby, British Columbia, V5A 1S6, Canada. gries@sfu.ca"
Journal Title:		J Chem Ecol
Year:		2021
Volume:		20210219
Issue:		2
Page Number:		123 - 133
DOI:		10.1007/s10886-020-01241-y
ISSN/ISBN:		1573-1561 (Electronic) 0098-0331 (Linking)
Abstract:		"Wireworms, the larvae of click beetles (Coleoptera: Elateridae), are soil-dwelling insect pests inflicting major economic damage on many types of agricultural crops worldwide. The objective of this work was to identify the female-produced sex pheromones of the Pacific Coast wireworm, Limonius canus LeConte, and the sugarbeet wireworm, L. californicus (Mannerheim) (Coleoptera: Elateridae). Headspace volatiles from separate groups of female L. canus and L. californicus were collected on Porapak Q and analyzed by gas chromatography with electroantennographic detection (GC-EAD) and GC-mass spectrometry. GC-EAD recordings revealed strong responses from male L. canus and male L. californicus antennae to the same compound, which appeared below GC detection threshold. The structure of this candidate pheromone component was deduced from the results of micro-analytical treatments of extracts, retention index calculations on four GC columns, and by syntheses of more than 25 model compounds which were assessed for their GC retention characteristics and electrophysiological activity. The EAD-active compound was identified as (E)-4-ethyloct-4-enoic acid, which we name limoniic acid. In field experiments in British Columbia and Alberta, Canada, traps baited with synthetic limoniic acid captured large numbers of male Limonius click beetles, whereas unbaited control traps captured few. Compared to traps baited with the analogue, (E)-5-ethyloct-4-enoic acid, traps baited with limoniic acid captured 9-times more male L. californicus, and 6.5-times more male western field wireworms, L. infuscatus Motschulsky, but 2.3-times fewer male L. canus. Limoniic acid can now be developed for detection, monitoring and possibly control of L. californicus, L. infuscatus and L. canus populations"
Keywords:		Animals Coleoptera/*chemistry/physiology Female Male Sex Attractants/*chemistry/physiology (E)-4-Ethyloct-4-enoic acid (E)-5-Ethyloct-4-enoic acid Elaterid beetles Gc-ead Gc-ms Limonius infuscatus Wireworms;
Notes:		"MedlineGries, Regine Alamsetti, Santosh K van Herk, Willem G Catton, Haley A Meers, Scott Lemke, Emily Gries, Gerhard eng IRC/Natural Sciences and Engineering Research Council of Canada/ IRC/Scotts Canada Ltd./ IRC/BASF Canada Inc./ 2021/02/20 J Chem Ecol. 2021 Feb; 47(2):123-133. doi: 10.1007/s10886-020-01241-y. Epub 2021 Feb 19"