Journal of Chemical Ecology

, Volume 32, Issue 1, pp 195-219

First online:

Identification of Components of Male-Produced Pheromone of Coffee White Stemborer, Xylotrechus quadripes

  • D. R. HallAffiliated withNatural Resources Institute, University of Greenwich Email author 
  • , A. CorkAffiliated withNatural Resources Institute, University of Greenwich
  • , S. J. PhythianAffiliated withNatural Resources Institute, University of Greenwich
  • , S. ChittamuruAffiliated withNatural Resources Institute, University of Greenwich
  • , B. K. JayaramaAffiliated withCentral Coffee Research Institute
  • , M. G. VenkateshaAffiliated withCentral Coffee Research InstituteDepartment of Zoology, Jnana Bharathi Campus, Bangalore University
  • , K. SreedharanAffiliated withCentral Coffee Research Institute
  • , P. K. Vinod KumarAffiliated withCentral Coffee Research Institute
  • , H. G. SeetharamaAffiliated withCentral Coffee Research Institute
    • , R. NaiduAffiliated withCentral Coffee Research Institute

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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.

Key Words

Xylotrechus quadripes coffee white stem borer Coleoptera Cerambycidae male sex pheromone (S)-2-hydroxy-3-decanone 3-hydroxy-2-decanone (S,S)-2,3-dihydroxyoctane Demonax balyi