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.
Similar content being viewed by others
References
R. Bel-Rhlid A. Fauve H. Veschambre (1989) ArticleTitleSynthesis of the pheromone components of the grape borer, Xylotrechus pyrrhoderus by microbiological reduction of an α-diketone J. Org. Chem. 54 3221–3223 Occurrence Handle10.1021/jo00274a053 Occurrence Handle1:CAS:528:DyaL1MXkt1SnsL8%3D
C. Bonini G. Righi (1992) ArticleTitleDiols obtained via chemo- and regioselective ring opening of epoxy alcohols: a straightforward synthesis of 2S,3S-octanediol Tetrahedron 48 1531–1538 Occurrence Handle1:CAS:528:DyaK38XhvFeqtLw%3D
C. Bonini C. Federici L. Rossi G. Righi (1995) ArticleTitleC-1 reactivity of 2,3-epoxy alcohols via oxirane opening with metal halides: application and synthesis of naturally occurring 2,3-octanediol, muricatacin, 3-octanol, and 4-dodecanolide J. Org. Chem. 60 4803–4812 Occurrence Handle10.1021/jo00120a025 Occurrence Handle1:CAS:528:DyaK2MXmvVejsbY%3D
S. Chattopadhyay V. R. Mamdapur M. S. Chadha (1990) ArticleTitleA convergent synthesis of (R)- and (S)-octan-3-ol and (2S,3S)-octane-2,3-diol, the pheromone components of myrmecine ants and the grape borer J. Chem. Res. (M) 8 1818–1823
E. J. Corey J. W. Suggs (1975) ArticleTitlePyridinium chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds Tetrahedron Lett. 16 2647–2650
A. Cork P. S. Beevor J. E. Gough D. R. Hall (1990) Gas chromatography linked to electroantennography: a versatile technique for identifying insect semiochemicals A. R. McCaffery I. D. Wilson (Eds) Chromatography and Isolation of Insect Hormones and Pheromones Plenum Press London 271–279
R. Fettköther K. Dettner F. Schröder H. Meyer W. Francke U. Noldt (1995) ArticleTitleThe male pheromone of the old house borer Hylotrupes bajulus (L.) (Coleoptera: Cerambycidae)—identification and female response Experientia 51 270–277
Hall, D. R., Cork, A., Phythian, S., Sumathi, C., Jayarama, B. K., Venkatesha, M. G., D'Souza, V. M., and Naidu, R. 1998. Studies on the male sex pheromone of the coffee white stemborer, Xylotrechus quadripes Chevrolat (Coleoptera: Cerambycidae). 2nd International Symposium on Insect Pheromones, Wageningen, The Netherlands, March 1998, pp. 50–52.
K. Iwabuchi (1982) ArticleTitleMating behaviour of Xylotrechus pyrrhoderus Bates (Coleoptera: Cerambycidae). I. Behavioural sequence and existence of the male sex pheromone Appl. Entomol. Zool. 17 494–500
K. Iwabuchi J. Takahashi T. Sakai (1987) ArticleTitleOccurrence of 2,3-octanediol and 2-hydroxy-3-octanone, possible male sex pheromone in Xylotrechus chinensis Chevrolat (Coleoptera: Cerambycidae) Appl. Entomol. Zool. 22 110–111 Occurrence Handle1:CAS:528:DyaL2sXkslCmu7Y%3D
S.-K. Kang D.-H. Lee J.-M. Lee (1990) ArticleTitleSynthesis of (2S,3S)-2,3-octanediol, the male sex pheromone of the grape borer, Xylotrechus pyrrhoderus Bull. Korean Chem. Soc. 11 274–275 Occurrence Handle1:CAS:528:DyaK3MXitlGktQ%3D%3D
Y. Kuwahara S. Matsuyama T. Suzuki (1987) ArticleTitleIdentification of 2,3-octanediol, 2-hydroxy-3-octanone and 3-hydroxy-2-octanone from male Xylotrechus chinensis Chevrolat as possible sex pheromones (Coleoptera: Cerambycidae) Appl. Entomol. Zool. 22 25–28 Occurrence Handle1:CAS:528:DyaL2sXkslCmu7k%3D
E. S. Lacey M. D. Ginzel J. G. Millar L. M. Hanks (2004) ArticleTitleMale-produced aggregation pheromone of the cerambycid beetle Neoclytus acuminatus acuminatus J. Chem. Ecol. 30 1493–1507 Occurrence Handle10.1023/B:JOEC.0000042064.25363.42 Occurrence Handle1:CAS:528:DC%2BD2cXns1Oltbg%3D Occurrence Handle15537155
W. S. Leal X. Shi K. Nakamuta M. Ono J. Meinwald (1995) ArticleTitleStructure, stereochemistry and thermal isomerization of the male sex pheromone of the longhorn beetle, Anaglyptus subfasciatus Proc. Natl. Acad. Sci. USA 92 1038–1042 Occurrence Handle1:CAS:528:DyaK2MXjslehu7c%3D Occurrence Handle7862629
R. H. Pelley ParticleLe (1968) Pests of Coffee Longmans, Green and Co., Ltd. London
W. D. Morewood K. E. Hein P. J. Katinic J. H. Borden (2002) ArticleTitleAn improved trap for large wood-boring insects, with special reference to Monochamus scutellatus (Coleoptera: Cerambycidae) Can. J. For. Res. 32 519–525 Occurrence Handle10.1139/x01-224
K. Mori T. Otsuka (1985) ArticleTitleSynthesis of (2S,3S)-2,3-octanediol and (S)-2-hydroxy-3-octanone, the male sex pheromone of the grape borer, Xylotrechus pyrrhoderus Tetrahedron 41 553–556 Occurrence Handle1:CAS:528:DyaL2MXkt1ags78%3D
K. Nakamuta W. S. Leal T. Nakashima M. Tokoro M. Ono M. Nakanishi (1997) ArticleTitleIncrease of trap catches by a combination of male sex pheromones and floral attractant in longhorn beetle, Anaglyptus subfasciatus J. Chem. Ecol. 23 1635–1640 Occurrence Handle10.1023/B:JOEC.0000006427.56337.6c Occurrence Handle1:CAS:528:DyaK2sXksFCqsbY%3D
C. Paolucci C. Mazzini A. Fava (1995) ArticleTitleDihydro- and tetrahydrofuran building blocks from 1,4:3,6-dianhydrohexitols. 2. Synthesis of acetal, alcohol, diol, epoxide, hydrocarbon and lactone pheromones J. Org. Chem. 60 169–175 Occurrence Handle10.1021/jo00106a030 Occurrence Handle1:CAS:528:DyaK2MXivVeqs7c%3D
M. Rhainds C. C. Lan S. King R. Gries L. Z. Mo G. Gries (2001a) ArticleTitlePheromone communication and mating behaviour of coffee white stem borer, Xylotrechus quadripes Chevrolat (Coleoptera: Cerambycidae) Appl. Entomol. Zool. 36 299–309 Occurrence Handle10.1303/aez.2001.299 Occurrence Handle1:CAS:528:DC%2BD3MXmvFOjtr0%3D
M. Rhainds M. Warndorff K. C. Phang C. L. Chin G. Gries (2001b) ArticleTitleStimuli increasing oviposition by female coffee white stem borer (Coleoptera: Cerambycidae) Can. Entomol. 133 409–412
M. Rhainds C. L. Chin L. Z. Mo G. Gries (2002) ArticleTitleIncidence, symptoms and intensity of damage by three coffee stem borers (Coleoptera: Cerambycidae) in South Yunan, China J. Econ. Entomol. 95 106–112 Occurrence Handle11942744
T. Sakai Y. Nakagawa J. Takahashi K. Iwabuchi K. Ishii (1984) ArticleTitleIsolation and identification of the male sex pheromone of the grape borer Xylotrechus pyrrhoderus Bates (Coleoptera: Cerambycidae) Chem. Lett. 1984 263–264
F. Schröder R. Fettköther U. Noldt K. Dettner W. A. König W. Francke (1994) ArticleTitleSynthesis of (3R)-3-hydroxy-2-hexanone, (2R,3R)-2,3-hexanediol and (2S,3R)-2,3-hexanediol, the male sex pheromone of Hylotrupes bajulus and Pyrrhidium sanguineum (Cerambycidae) Liebigs Ann. Chem. 1994 1211–1218
K. B. Sharpless W. Amberg Y. L. Bennani G. A. Crispino J. Hartung K.-S. Jeong H.-L. Kwong K. Morikawa Z.-M. Wang D. Xu X.-L. Zhang (1992) ArticleTitleThe osmium-catalyzed asymmetric dihydroxylation: a new ligand class and a process improvement J. Org. Chem. 57 2768–2771 Occurrence Handle10.1021/jo00036a003 Occurrence Handle1:CAS:528:DyaK38XitlGqsb4%3D
K. Sreedharan P. K. V. Kumar (2001) ArticleTitleManaging the white stem borer—key issues Indian Coffee 65 13–15
H. Takahata Y. Uchida T. Momose (1994) ArticleTitleNew synthesis of all four isomers of 3-hydroxy-4-methyl-γ-butyrolactone by stereoselective intramolecular lactonization. Application to asymmetric synthesis of biologically active compounds J. Org. Chem. 59 7201–7208 Occurrence Handle10.1021/jo00103a008 Occurrence Handle1:CAS:528:DyaK2MXhvVentbw%3D
K. Venkateshu P. Krishnamoorthy Bhat K. Bhaskara Reddy P. K. Ramaiah (1986) ArticleTitlePreliminary studies on pheromone of coffee white stem-borer, Xylotrechus quadripes Chev J. Coffee Res. 16 111–113
M. G. Venkatesha P. Krishnamoorthy Bhat H. G. Seetharama (1995) ArticleTitleCourtship behaviour of the coffee white stem borer, Xylotrechus quadripes Chevr. (Coleoptera: Cerambycidae) J. Coffee Res. 25 88–93
J. Visitpanich (1994) ArticleTitleThe biology and survival rate of the coffee stem borer, Xylotrechus quadripes Chevrolat (Coleoptera, Cerambycidae) in northern Thailand Jap. J. Entomol. 62 731–745
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
Authors and Affiliations
Corresponding author
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
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10886-006-9360-0