Hall, David R. ORCID: 0000-0002-7887-466X, Cork, Alan, Phythian, Sara J., Chittamuru, S., Jayarama, B.K., Venkatesha, M.G., Sreedharan, K., Vinod Kumar, P.K., Seetharama, H.G. and Naidu, R. (2006) Identification of components of male-produced pheromone of coffee white stemborer, Xylotrechus quadripes. Journal of Chemical Ecology, 32 (1). pp. 195-219. ISSN 0098-0331 (doi:https://doi.org/10.1007/s10886-006-9360-0)

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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 mg hrj1 insectj1 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

Item Type:	Article
Uncontrolled Keywords:	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
Subjects:	S Agriculture > S Agriculture (General) Q Science > QL Zoology S Agriculture > SB Plant culture
Faculty / School / Research Centre / Research Group:	Faculty of Engineering & Science > Natural Resources Institute Faculty of Engineering & Science > Natural Resources Institute > Agriculture, Health & Environment Department
Related URLs:	Publisher Organisation Organisation
Last Modified:	29 Jan 2020 13:39
URI:	http://gala.gre.ac.uk/id/eprint/3180

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