Identification of a hyperactive pheromone analog in field tests of pheromone mimics for two click beetle species in the
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CHEMOECOLOGY
ORIGINAL ARTICLE
Identification of a hyperactive pheromone analog in field tests of pheromone mimics for two click beetle species in the genus Cardiophorus (Coleoptera: Elateridae) Jacqueline M. Serrano1,2 · Yunfan Zou1 · Jocelyn G. Millar1,3 Received: 17 March 2020 / Accepted: 11 July 2020 © This is a U.S. government work and its text is not subject to copyright protection in the United States; however, its text may be subject to foreign copyright protection 2020
Abstract Females of two click beetle species, Cardiophorus tenebrosus and C. edwardsi (Coleoptera: Elateridae), produce methyl (3R,6E)-2,3-dihydrofarnesoate as their sex pheromone. We had serendipitously discovered that males of both species were also strongly attracted to (R)-fuscumol acetate ((E)-6,10-dimethylundeca-5,9-dien-2-yl acetate), a known longhorned beetle (Coleoptera: Cerambycidae) pheromone, due to its structural similarities to the click beetle pheromone. To further investigate the specificity of the responses of Cardiophorus males, additional analogs with different chain lengths and structural relationships compared to the natural pheromone were synthesized and tested. In field and electroantennogram bioassays, only fuscumol propionate ((E)-6,10-dimethylundeca-5,9-dien-2-yl propionate) elicited strong responses from Cardiophorus males, indicating that they were able to distinguish chain length and spatial relationships between the structural elements. In field trials, C. tenebrosus males were attracted equally to the analog and their natural pheromone, but the pheromone elicited stronger antennal responses from males. In contrast, traps baited with fuscumol propionate caught approximately 26 times as many C. edwardsi males compared to traps baited with the natural pheromone, although the analog elicited significantly smaller antennal responses from C. edwardsi males. Thus, in terms of behavioral responses, fuscumol propionate appears to be acting as a hyperactive pheromone mimic, a phenomenon which has rarely been observed in insect semiochemistry. Keywords Elateridae · Click beetle · Pheromone analog · (E)-6,10-dimethylundeca-5,9-dien-2-yl propionate · Methyl (3R,6E)-2,3-dihydrofarnesoate
Introduction Communication by means of volatile pheromones is probably the most widespread form of intraspecific communication in the Insecta, and thousands of insect pheromones have now been identified from across the insect taxa (Symonds Handling Editor: Günther Raspotnig. * Jacqueline M. Serrano [email protected] 1
Department of Entomology, University of California, Riverside, CA 92521, USA
2
Present Address: Temperate Tree Fruit and Vegetable Research Unit, USDA-ARS, 5230 Konnowac Pass Rd, Wapato, WA 98951, USA
3
Department of Chemistry, University of California, Riverside, CA 92521, USA
and Elgar 2008; El-Sayed 2019). The use of pheromones as a means of communication is highly efficient, with behavioral responses and/or physiological changes often being elicited by only a few molecules of pheromone. Genera
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