Blends of ( R )-3-hydroxyhexan-2-one and alkan-2-ones identified as potential pheromones produced by three species of ce
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CHEMOECOLOGY
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Blends of (R)-3-hydroxyhexan-2-one and alkan-2-ones identified as potential pheromones produced by three species of cerambycid beetles Robert F. Mitchell • Jocelyn G. Millar Lawrence M. Hanks
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Received: 24 August 2012 / Accepted: 9 November 2012 / Published online: 29 November 2012 Ó Springer Basel 2012
Abstract We present data indicating that three species of cerambycid beetles (subfamily Cerambycinae) produce the common cerambycine pheromone component (R)-3-hydroxyhexan-2-one as well as an alkan-2-one component, a possible new motif for cerambycid pheromone components. GC/MS analyses of headspace volatiles produced by male beetles indicated that Cyrtophorus verrucosus (Olivier) produced (R)-3-hydroxyhexan-2-one but also nonan-2-one at *18 % of the hydroxyketone component, whereas Orwellion gibbulum arizonense (Casey) and Parelaphidion aspersum (Haldeman) produced decan2-one at *40 and 7 % of the amount of the hydroxyketone, respectively. In field bioassays, adult C. verrucosus were attracted by (R)-3-hydroxyhexan-2-one alone, but attraction was significantly enhanced by nonan-2-one. This effect was lost if the quantity of nonan-2-one exceeded 100 % of the hydroxyketone, suggesting that beetles could discern ratios of the two chemicals and were most strongly attracted to those approximating the blend produced by males. We suggest that nonan-2-one plays a role in the
R. F. Mitchell L. M. Hanks Department of Entomology, University of Illinois at UrbanaChampaign, Urbana, IL 61801, USA L. M. Hanks e-mail: [email protected] J. G. Millar Department of Entomology, University of California, Riverside, CA 92521, USA Present Address: R. F. Mitchell (&) Center for Insect Science, University of Arizona, Tucson, AZ 85721, USA e-mail: [email protected]
species specificity of the pheromone signal of C. verrucosus, and that decan-2-one plays a similar role in the semiochemical communication of O. g. arizonense and P. aspersum. Keywords Sex pheromone Reproductive isolation Longhorned beetle Nonan-2-one Decan-2-one
Introduction Pheromone chemistry appears to be remarkably conserved among closely related and even quite distantly related species of cerambycid beetles, to the extent that some species produce a single chemical that potentially could attract many other species (e.g., Barbour et al. 2011; Hanks et al. 2012; Hanks and Millar 2012; Macias-Samano et al. 2012). For example, (R)-3-hydroxyhexan-2-one (hereafter ‘‘3R-ketone’’) appears to be the sole or primary component of aggregation pheromones for many sympatric and synchronic species in the subfamily Cerambycinae, with the result that traps baited with the synthetic compound capture multiple species (e.g., Hanks and Millar 2012; Hanks et al. 2007, 2012; Lacey et al. 2007, 2009; Wong et al. 2012). Species may avoid cross attraction by differential responses to certain host plant volatiles in combination with the pheromone, or by differing in seasonal or circadian activity periods (e.g., Hanks et al. 2012). Spe
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