Skip to main content

Advertisement

Log in

A Symmetrical Diester as the Sex Attractant Pheromone of the North American Click Beetle Parallelostethus attenuatus (Say) (Coleoptera: Elateridae)

  • Published:
Journal of Chemical Ecology Aims and scope Submit manuscript

Abstract

Hexanoic acid, 1-octanol, 1,8-octanediol, octyl hexanoate, 1,8-octanediol monohexanoate, and 1,8-octanediol dihexanoate were identified in headspace volatiles collected from the crushed abdomen of a female click beetle of the species Parallelostethus attenuatus (Say) (Elaterinae, tribe Elaterini). In field trials carried out in Illinois, South Carolina, North Carolina, and Virginia, adult male beetles were strongly attracted to 1,8-octanediol dihexanoate alone. Blends of the dihexanoate with one or more of the other compounds proved to be less attractive than the dihexanoate alone, suggesting that the pheromone of this species may consist of a single compound. The symmetrical diester structure of the pheromone is a novel natural product and appears to be structurally unique among insect pheromones.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  • Ahsan M, Sung S, Jeon H, Patil M, Chung T, Yun H (2018) Biosynthesis of medium- to long-chain α, ω-diols from free fatty acids using CYP153A monooxygenase, carboxylic acid reductase, and E. coli endogenous aldehyde reductases. Catalysts 8:4. https://doi.org/10.3390/catal8010004

    Article  CAS  Google Scholar 

  • Blatchley WS (1910) An illustrated descriptive catalogue of the Coleoptera or beetles known to occur in Indiana. Nature Publishing Co., Indianapolis IN, USA 1385 pp.

    Google Scholar 

  • Dogger JR (1959) The Elateridae of Wisconsin I. A list of the species found in Wisconsin and keys to the identification of genera of adults and larvae. Wisconsin Acad Sci Arts Lett 48:103–120

    Google Scholar 

  • El-Sayed AM (2019) The Pherobase: database of pheromones and semiochemicals. http://www.pherobase.com. Accessed Dec. 8, 2021

  • Graham EE, Mitchell RF, Reagel PF, Barbour JD, Millar JG, Hanks LM (2010) Treating panel traps with a fluoropolymer enhances their efficiency in capturing cerambycid beetles. J Econ Entomol 103:641–647

    Article  Google Scholar 

  • Gries R, Alamsetti SK, van Herk WG, Catton HA, Meers S, Lemke E, Gries G (2021) Limoniic acid – major component of the sex pheromone of the click beetles Limonius canus and L. californicus. J Chem Ecol 47:123–133

    Article  CAS  Google Scholar 

  • Jansson RK, Seal DR (1994) Biology and management of wireworms on potato. In: Zehnder GW, Powelson ML, Jansson RK, Raman KV (eds) Advances in potato pest management. APS Press, St. Paul, MN, USA, pp 31–53

    Google Scholar 

  • Jewett HH (1946) Identification of some larval Elateridae found in Kentucky. Ky Ag Expt Stn Bull 489:1–40

    Google Scholar 

  • Johnson PJ (2002) Elateridae Leach 1815. In: Arnett H Jr, Thomas MC, Skelley PE, Frank JH (eds) American beetles, Polyphaga: Scarabaeoidea through Curculionoidea, Volume 2. CRC Press, Boca Raton, FL, USA, pp 160–173

  • Kirk HB (1922) Biological notes on Elateridae and Melasidae (Col.). Entomol News 33:236–240

    Google Scholar 

  • Lindroth E, Clark TL (2009) Phylogenetic analysis of an economically important species complex of wireworms (Coleoptera: Elateridae) in the Midwest. J Econ Entomol 109:743–749

    Article  Google Scholar 

  • Porcher RD, Rayner DA (2001) A guide to the wildflowers of South Carolina. University of South Carolina Press, Columbia, SC, USA

    Google Scholar 

  • Roache LC (1960) A revision of the North American elaterid beetles of the tribe Elaterini (Coleoptera: Elateridae). Trans Am Entomol Soc 86:275–324

    Google Scholar 

  • SAS Institute (2011) SAS/STAT 9.3 User’s Guide. SAS Institute Inc., Cary, NC, USA

    Google Scholar 

  • Serrano JM, Collignon RM, Zou Y, Millar JG (2018) Identification of sex pheromones and sex pheromone mimics for two North American click beetle species (Coleoptera: Elateridae) in the genus Cardiophorus Esch. J Chem Ecol 44:327–338

    Article  CAS  Google Scholar 

  • Smith JW, Enns WR (1977) The click beetle subfamilies Agrypninae, Pyrophorinae, and Melanotinae (Coleoptera: Elateridae) in Missouri: part I. J Kansas Entomol Soc 50:436–468

    Google Scholar 

  • Sokal RR, Rohlf FJ (1995) Biometry, 3rd edn. W. H. Freeman, New York, NY, USA

    Google Scholar 

  • Svensson GP, Liedtke C, Hedenström E, Breistein P, Bang J, Larsson MC (2012) Chemical ecology and insect conservation: optimising pheromone-based monitoring of the threatened saproxylic click beetle Elater ferrugineus. J Insect Conserv 16:549–555

    Article  Google Scholar 

  • Tolasch T, von Fragstein M, Steidle JLM (2007) Sex pheromone of Elater ferrugineus L. (Coleoptera: Elateridae). J Chem Ecol 33:2156–2166

    Article  CAS  Google Scholar 

  • Tolasch T, Von Fragstein M, Steidle JL (2010) Sex pheromone of Agriotes acuminatus (Stephens, 1830) (Coleoptera: Elateridae). J Chem Ecol 36:314–318

    Article  CAS  Google Scholar 

  • Tolasch T, von Fragstein M, Steidle JL (2022) Sex pheromone of the click beetle Agriotes pilosellus (Schönherr, 1718). J Chem Ecol 48:1–6

    Article  Google Scholar 

  • Tóth M (2013) Pheromones and attractants of click beetles: an overview. J Pest Sci 86:3–17

    Article  Google Scholar 

  • Vanderwel D, Pierce HD Jr, Oehlschlager AC, Borden JH, Pierce AM (1990) Macrolide (cucujolide) biosynthesis in the rusty grain beetle, Cryptolestes ferrugineus I. Insect Biochem 20:567–572

    Article  CAS  Google Scholar 

  • Vanderwel D, Johnston B, Oehlschlager AC (1992) Cucujolide biosynthesis in the merchant and rusty grain beetles. Insect Biochem Mol Biol 22:875–883

    Article  CAS  Google Scholar 

  • van Herk WG, Vernon RS, Borden JH (2018) A pheromone-baited pitfall trap for monitoring Agriotes spp. click beetles (Coleoptera: Elateridae) and other soil-surface insects. J Entomol Soc Br C 115:101–103

    Google Scholar 

  • van Herk WG, Lemke E, Gries G, Gries R, Serrano JM, Catton H, Wanner K, Landolt PJ, Cooper WR, Meers S, Nikoukar A (2021) Limoniic acid and its analog as trap lures for pest Limonius species (Coleoptera: Elateridae) in North America. J Econ Entomol 114:2108–2120

    Article  Google Scholar 

  • Williams L III, Serrano JM, Johnson PJ, Millar JG (2019) 13-Tetradecenyl acetate, a female-produced sex pheromone component of the economically important click beetle Melanotus communis (Gyllenhal) (Coleoptera: Elateridae). Sci Rep 9:1–12 (16197). https://doi.org/10.1038/s41598-019-52199-1

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We thank Aaron Blue, Emma Schoeppner, Kelly McIntyre, and Lance Lawrence for assistance with field work. We appreciate funding support from the USDA-ARS State Potato Partnership Funds projects 2092-22000-022-00D and 6080-22000-030-00D.

Funding

LMH, JGM, ASH, TPK, and LW III appreciate funding support from the USDA-ARS State Potato Partnership Funds projects 2092-22000-022-00D and 6080-22000-030-00D.

Author information

Authors and Affiliations

Authors

Contributions

JGM, LW III, and LMH secured the funding in support of the work described. JGM identified and synthesized possible pheromone compounds and contributed to writing the manuscript. LW III, ASH, and TPK carried out field trials and contributed sections of the manuscript. JMS and SH prepared and carried out analyses of pheromone extracts. ACG assisted with field trials in Illinois. LMH organized the field work in Illinois, carried out the data analyses, and contributed to writing the manuscript. All authors assisted in editing and polishing the manuscript.

Corresponding author

Correspondence to Jocelyn G. Millar.

Ethics declarations

Competing Interests

The authors declare that they have no competing interests.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Millar, J.G., Williams, L., Serrano, J.M. et al. A Symmetrical Diester as the Sex Attractant Pheromone of the North American Click Beetle Parallelostethus attenuatus (Say) (Coleoptera: Elateridae). J Chem Ecol 48, 598–608 (2022). https://doi.org/10.1007/s10886-022-01360-8

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10886-022-01360-8

Keywords

Navigation