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Pheromone Communication and Mating Behaviour of Coffee White Stem Borer, Xylotrechus Quadripes Chevrolat (Coleoptera: Cerambycidae)

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Pheromone Communication and Mating Behaviour of Coffee White Stem Borer, Xylotrechus Quadripes Chevrolat (Coleoptera: Cerambycidae) Appl. Entomol. Zool. 36 (3): 299–309 (2001) Pheromone communication and mating behaviour of coffee white stem borer, Xylotrechus quadripes Chevrolat (Coleoptera: Cerambycidae) Marc Rhainds,* Chin Chiew Lan,1 Skip King, Regine Gries, Li Zhen Mo2 and Gerhard Gries Center for Environmental Biology, Department of Biological Sciences, Simon Fraser University, Burnaby, B.C., V5A 1S6, Canada 1 Nestlé R&D Center Sdn. Bhd., P.O. Box 185, 08000 Sg. Petani, Kedah D.A., Malaysia 2 Nestlé Agricultural Service Liaison Office, 19 Renmin Donglu, 650051 Kunming, Yunan, China (Received 10 July 2000; Accepted 16 February 2001) Abstract This study investigated pheromone communication and mating behaviour of the coffee white stem borer (CWSB), Xy- lotrechus quadripes (Coleoptera: Cerambycidae), in South Yunan, China. Coupled gas chromatographic-electroan- tennographic detection (GC-EAD) and GC-mass spectrometric (MS) analyses of volatiles released by male and fe- male CWSB identified 2-hydroxy-3-decanone and 2,3-decanedione as male-specific candidate pheromones. Further GC-EAD and GC-MS analyses confirmed that only (S)-2-hydroxy-3-decanone is produced by male CWSB and elicits antennal responses by male and female CWSB. In field experiments, 2-hydroxy-3-decanone as a trap bait afforded capture of one female CWSB, and in laboratory experiments it weakly attracted female but not male CWSB. Complex mating behaviour in CWSB includes: 1) attraction of potential mates by both sexes; 2) repeated landings (with ever decreasing distance) of a female next to a male; 3) males dashing to a nearby female; 4) rejection of mating attempts by females; 5) post-mating female guarding by males; and 6) size-dependent mating success of males. Considering this complex mating behaviour, lack of direct flight towards pheromone sources, mating near pheromone-baited traps, and only moderate attractiveness of (synthetic) pheromone, pheromone-based trapping of females does not seem to be a viable strategy for managing CWSB populations in China. Key words: Xylotrechus quadripes, coffee white stem borer, Cerambycidae, pheromone, mating behaviour Male CWSB from India produce (S)-2-hydroxy- INTRODUCTION 3-decanone as a female attracting pheromone (Hall The coffee white stem borer (CWSB), Xy- et al., 1998). This study was undertaken to investi- lotrechus quadripes (Chevrolat) (Coleoptera: Cer- gate pheromone communication and mating behav- ambicydae), is a major pest in commercial coffee iour of CWSB in South Yunan, China. Specific ob- plantations in Asia (Duffy, 1968; Visitpanich, jectives were to: 1) identify pheromone compo- 1992a; Kuang et al., 1997; Rhainds et al., 2001a). nents; 2) evaluate behavioural activity of candidate Damage inflicted to coffee stems by wood-feeding pheromones; 3) document pre-mating interactions larvae causes mortality of plants or reduction in between adults; and 4) quantify intraspecific varia- fruit production (Veeresh, n.d.). Because larvae in- tions of mating success. side coffee stems are difficult to control, manage- ment strategies are aimed at preventing infestation, MATERIALS AND METHODS either by manually collecting adults, uprooting infested stems, or interfering with oviposition Identification of candidate pheromone. Three behaviour by scrubbing stems or swabbing them shipments of adult CWSB were sent from South with repellent chemicals (Veeresh, n.d.). Recently, Yunan to Simon Fraser University. Volatiles re- pheromone-based monitoring and/or mass trapping leased by males or females (Visitpanich, 1994) of CWSB populations have been considered as po- were captured in 6 separate aerations. Groups of tential management tactics. 15, 21 or 25 males, and of 12, 22 or 36 females, * To whom correspondence should be addressed at: Department of Entomology, New York State Agricultural Experiment Station, Cornell Univer- sity, Geneva, NY 14456, U.S.A. 299 300 M. Rhainds et al. were placed in a cylindrical Pyrex glass chamber trimethylsilyl cyanide (25 g) were dissolved in (Oehlschlager et al., 1988). A water aspirator drew dichloromethane (150 ml), and zinc bromide charcoal filtered, humidified air at 2 l/min through (0.6 g) was added at 0°C. After 15 min, the mixture the chamber and a glass column (14 cmϫ13 mm was stirred for 2 days at room temperature, then OD) filled with Porapak Q (50–80 mesh, Waters washed twice (water, sat aq. sodium chloride), Associate Inc., Massachusetts 01757). Volatiles dried and evaporated. After distillation at 66– were eluted from the Porapak Q with 5 ml of redis- 68°C @ 20 torr., compound 4 (30.3 g, 85% yield) 1 tilled pentane. Aliquots of 0.1–1.0 beetle-aeration- was obtained. H (CDCl3); d ppm 0.2 (9H, s), 1.55 hours were subjected to gas chromatographic (GC) (3H, d), 4.51 (1H, q); GC-MS m/z (relative inten- analyses (Hewlett-Packard 5890) with both flame sity): 143 (1), 127 (8), 117 (35), 101 (100). ionization (FID) and electroantennographic detec- 2-Hydroxy-3-decanone (6) (Fig. 1, Scheme 2): tion (EAD) (Arn et al., 1975), employing 3 fused A Grignard reagent was prepared from bromohep- silica columns (30 mϫ0.25 or 0.32 mm ID) with tane (45.6 g) and Mg (7 g) in ether (200 ml). This different retention characteristics (DB-5, DB-210, was cooled to Ϫ70°C, and compound 4 added. The DB-23; J&W Scientific, Folsom, California 95630). mixture was allowed to warm to ambient tempera- Full-scan electron impact (EI) and chemical ioniza- ture, and was stirred overnight. The reaction was tion (isobutane) (CI) mass spectra of EAD-active quenched with water, then diluted slowly with sat. compounds were obtained by coupled GC-mass ammonium chloride (80 ml) and stirred until solids spectrometry (MS), using a Varian Saturn II ion dissolved. After acidifying to pH 4, the mixture trap GC-MS and an HP 5985 GC-MS, respectively, was extracted 3 times with hexane/ether (50/50). each fitted with the DB-210 or DB-5 column re- Combined extracts were washed (water, brine), ferred to above. Enantiomeric composition of can- dried and evaporated. Crude 5 was treated at 0°C didate pheromone 2-hydroxy-3-decanone was de- with a solution of HF (47%, 13 ml) in acetonitrile termined by GC, GC-EAD and GC-MS of Porapak (120 ml). After being stirred for 1 h, the mixture Q extracts, employing a fused silica column (30 mϫ was diluted with water (100 ml) and extracted 3 0.25 mm ID) coated with Cyclodex B (J&W Scien- times with hexane/ether (50/50). Combined or- tific). Comparative split/splitless (240°C) and on- ganic layers were washed (water, brine), dried and column (50°C) GC injection of volatile extract was evaporated. Chromatography yielded 90% chemi- conducted to reveal potential thermal rearrange- cally pure (GC) colourless 6 (24 g; 75% overall 1 ment of candidate pheromones. yield). H (CDCl3); d ppm 0.88 (3H, t), 1.20–1.32 Syntheses (10H, m), 1.38 (3H, d), 2.35–2.55 (2H, m), 4.28 2,3-Decanedione (2) (Fig. 1, Scheme 1): 2- (1H, q); GC-MS m/z (relative intensity): 172 (60), Decene (1; 6.6 g in 220 ml of acetone, 50 ml of 154 (10), 136 (12), 126 (50), 109 (15), 108 (15), 57 H2O, and 6.1 ml of acetic acid), which was pro- (100), 45 (65), 43 (55). duced by Wittig reaction of octanal and ethyl- O-Trimethylsilyl-octanal cyanohydrin (8b) (Fig. triphenyl-phosphonium bromide, was oxidized by 1, Scheme 3): To octanal (8 g) in MeOH (30 ml) potassium permanganate (10.3 g in 20 ml of H2O) was added potassium cyanide (4.6 g), followed by (Srinivasan and Lee, 1979). The resulting mixture acetic acid (4.8 ml). After 18 h, water was added of the diketone and ketoalcohols was further oxy- and the mixture extracted to yield crude 8a (8.5 g). dized by heating for 2 min with cupric acetate This was redissolved in dichloromethane (50 ml) (18 g in 20 ml of H2O and 25 ml of acetic acid) and combined with trimethylsilyl chloride (7 g), (Lewbart and Mattox, 1963). Further addition of triethylamine (10 ml), and DMAP (1 g). After 2 h cupric acetate (5 g) and 2-min-heating yielded after of stirring the reaction was complete. Water was purification bright yellow 2,3-decanedione (2, added, and the mixture extracted 3 times with 1 3.9 g). H (CDCl3); d ppm 0.87 (3H, t), 1.20–1.33 hexane/ether (50/50). Combined organic layers (8H, m), 1.56 (2H, m), 2.31 (3H, s), 2.71 (2H, t); were washed (10% sulfuric acid, brine) and dried GC-MS m/z (relative intensity): 170 (1), 126 (35), (sodium sulfate and charcoal). After evaporation 108 (10), 56 (100), 43 (58). and chromatography, product 8b (6.8 g, 74% pure) O-Trimethylsilyl-acetaldehyde cyanohydrin (4) was obtained admixed with a minor by-product; (Fig. 1, Scheme 2): Acetaldehyde (3, 12 g) and GC-MS m/z (relative intensity): 227 (2), 212 (72), Chemical Ecology of Coffee White Stem Borer 301 201 (15), 185 (100); by-product: 256 (12), 145 (85). 3-Hydroxy-2-decanone (9) (Fig. 1, Scheme 3): To the mixture of 8b plus by-product (3.4 g) dis- solved in ether (20 ml) at Ϫ70°C was added drop- wise MeLi (1.5 M, 10 ml). The solution was stirred 1 h under argon and quenched cold with saturated ammonium chloride. After the mixture had warmed to 25°C, DME (30 ml) and 2 N HCl (30 ml) were added, followed by HF (47%, 0.8 ml). When TLC indicated the absence of silyl ether, the mixture was extracted with mixed solvent. Com- bined organic phases were washed (brine), dried and evaporated. The crude product was chro- matographed to yield pure ketoalcohol (9, 1.1 g); GC-MS m/z (relative intensity): 172 (8), 128 (12), 111 (15), 110 (12), 69 (100), 74 (6), 43 (55).
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