Identification of Components of Male-Produced Pheromone of Coffee White Stemborer, Xylotrechus quadripes (original) (raw)

Abstract

The coffee white stem borer, Xylotrechus quadripes Chevrolat (Coleoptera: Cerambycidae), is the foremost pest of arabica coffee in India, Sri Lanka, China, Vietnam, and Thailand. Previous work showed that female beetles were attracted to traps baited with male beetles. Analyses of volatiles from male X. quadripes of Indian origin by gas chromatography (GC) linked to electroantennographic (EAG) recording from a female beetle antenna showed three male-specific components comprising more than 90% of the volatiles, two of which elicited EAG responses. The major EAG-active component was produced at up to 2 μg hr−1 insect−1 and was identified as (S)-2-hydroxy-3-decanone (I) by comparison of GC data, and mass (MS), infrared, and nuclear magnetic resonance (NMR) spectra with those of synthetic standards. The second component was identified as 3-hydroxy-2-decanone (II) produced in part by isomerization of I under the conditions of the GC analysis, although the NMR spectrum suggested it is naturally produced at up to 7% of I. The minor component that elicited an EAG response, present at 7% of the amount of I, was identified as (S,S)-2,3-dihydroxyoctane (III) from GC and MS data. 2-Hydroxy-3-octanone (0.2–0.5% of I), 2,3-decanedione (2% of I), 2-phenylethanol (3% of I), and octanoic acid (4% of I) were also identified in volatiles from male beetles. A general, stereospecific synthetic route to the enantiomers of 2-hydroxy-3-alkanones from the enantiomers of ethyl lactate was developed. The enantiomers of III were synthesized from (E)-2-octene by Sharpless asymmetric dihydroxylation. (S)-(I) was attractive to male X. quadripes in laboratory bioassays, but addition of (S,RS)-(III) at 10% of I reduced attractiveness. In field trials carried out in India with sticky, cross-vane traps, (S)- and (RS)-(I) attracted male X. quadripes and addition of (S,S)-(III) at 10% of I reduced attractiveness. Significant numbers of female Demonax balyi Pascoe (Coleoptera: Cerambycidae) were sometimes caught in traps baited with (S)-(I) alone.

Access this article

Log in via an institution

Subscribe and save

Buy Now

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

Instant access to the full article PDF.

Similar content being viewed by others

References

Download references

Acknowledgments

This publication is an output from research projects (R6928 and 7246) funded by the United Kingdom's Department for International Development (DFID). However, DFID accepts no responsibility for any information provided or views expressed. Demonax balyi beetles were identified by the CABI Identification Service.

Author information

Author notes

  1. M. G. Venkatesha
    Present address: Department of Zoology, Jnana Bharathi Campus, Bangalore University, Bangalore, 560 056, India

Authors and Affiliations

  1. Natural Resources Institute, University of Greenwich, Chatham Maritime, Kent, ME4 4TB, UK
    D. R. Hall, A. Cork, S. J. Phythian & S. Chittamuru
  2. Central Coffee Research Institute, 577 117 Chikmagalur District, Karnataka, India, TN
    B. K. Jayarama, M. G. Venkatesha, K. Sreedharan, P. K. Vinod Kumar, H. G. Seetharama & R. Naidu

Authors

  1. D. R. Hall
    You can also search for this author inPubMed Google Scholar
  2. A. Cork
    You can also search for this author inPubMed Google Scholar
  3. S. J. Phythian
    You can also search for this author inPubMed Google Scholar
  4. S. Chittamuru
    You can also search for this author inPubMed Google Scholar
  5. B. K. Jayarama
    You can also search for this author inPubMed Google Scholar
  6. M. G. Venkatesha
    You can also search for this author inPubMed Google Scholar
  7. K. Sreedharan
    You can also search for this author inPubMed Google Scholar
  8. P. K. Vinod Kumar
    You can also search for this author inPubMed Google Scholar
  9. H. G. Seetharama
    You can also search for this author inPubMed Google Scholar
  10. R. Naidu
    You can also search for this author inPubMed Google Scholar

Corresponding author

Correspondence toD. R. Hall.

Rights and permissions

About this article

Cite this article

Hall, D.R., Cork, A., Phythian, S.J. et al. Identification of Components of Male-Produced Pheromone of Coffee White Stemborer, Xylotrechus quadripes.J Chem Ecol 32, 195–219 (2006). https://doi.org/10.1007/s10886-006-9360-0

Download citation

Key Words