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Identification of Sex Pheromone Components of the Hessian Fly, Mayetiola Destructor

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Identification of Sex Pheromone Components of the Hessian Fly, Mayetiola Destructor J Chem Ecol (2009) 35:81–95 DOI 10.1007/s10886-008-9569-1 Identification of Sex Pheromone Components of the Hessian Fly, Mayetiola destructor Martin N. Andersson & Jenny Haftmann & Jeffrey J. Stuart & Sue E. Cambron & Marion O. Harris & Stephen P. Foster & Stephan Franke & Wittko Francke & Ylva Hillbur Received: 15 May 2008 /Revised: 15 September 2008 /Accepted: 5 November 2008 /Published online: 10 December 2008 # Springer Science + Business Media, LLC 2008 Abstract Coupled gas chromatographic (GC)–electroan- (with respect to the main compound, (2S,10E)-10-tridecen- tennographic detection (EAD) analyses of ovipositor 2-yl acetate). The five-component blend was more attractive extract of calling Hessian fly, Mayetiola destructor, females to male flies than a three-component blend lacking the two revealed that seven compounds elicited responses from dienes. Furthermore, the five-component blend was more male antennae. Four of the compounds—(2S)-tridec-2-yl attractive than a blend with the same compounds but that acetate, (2S,10Z)-10-tridecen-2-yl acetate, (2S,10E)-10- contained one tenth the concentration of (2S,8E,10E)-8, tridecen-2-yl acetate, and (2S,10E)-10-tridecen-2-ol—were 10-tridecadien-2-yl acetate (more accurately mimicking the identified previously in female extracts. Two new EAD- ratios found in female extract). This suggests that the ratios active compounds, (2S,8Z,10E)-8,10-tridecadien-2-yl acetate emitted by females might deviate from those in gland and (2S,8E,10E)-8,10-tridecadien-2-yl acetate, were identi- extracts. In a field-trapping experiment, the five-component fied by GC–mass spectroscopy (MS) and the use of synthetic blend applied to polyethylene cap dispensers in a 100:10 μg reference samples. In a Y-tube bioassay, a five-component ratio between the main component and each of the other blend (1 ng (2S)-tridec-2-yl acetate, 10 ng (2S,10E)-10- blend components attracted a significant number of male tridecen-2-yl acetate, 1 ng (2S,10E)-10-tridecen-2-ol, 1 ng Hessian flies. Also, a small-plot field test demonstrated the (2S,8Z,10E)-8,10-tridecadien-2-yl acetate, and 1 ng attractiveness of the five-component blend to male Hessian (2S,8E,10E)-8,10-tridecadien-2-yl acetate) was as attractive flies and suggests that this pheromone blend may be useful to male Hessian flies as a similar amount of female extract for monitoring and predicting Hessian fly outbreaks in agricultural systems. M. N. Andersson : Y. Hillbur (*) Department of Plant Protection Biology, Keywords Mayetiola destructor . Hessian fly. Swedish University of Agricultural Sciences, Cecidomyiidae . Diptera . Sex pheromone . (2S)-Tridec-2-yl 230 53 Alnarp, Sweden e-mail: [email protected] acetate . (2S,10E)-10-tridecen-2-yl acetate . : : (2S,10E)-10-Tridecen-2-ol (2S,8Z,10E)-8 J. Haftmann S. Franke W. Francke 10-Tridecadien-2-yl acetate . (2S,8E,10E)-8 . Institute of Organic Chemistry, University of Hamburg, 10-Tridecadien-2-yl acetate . GC–EAD . Y-tube bioassay. 20146 Hamburg, Germany Field trapping J. J. Stuart Department of Entomology, Purdue University, West Lafayette, IN 47907, USA Introduction S. E. Cambron USDA-ARS, Department of Entomology, Purdue University, The Hessian fly, Mayetiola destructor (Say) (Diptera: West Lafayette, IN 47907, USA Cecidomyiidae), is one of the most destructive pests of wheat (Triticum spp) in the US and North Africa (Gagné M. O. Harris : S. P. Foster Department of Entomology, North Dakota State University, 1989; El Bouhssini et al. 1999; Berzonsky et al. 2003; Fargo, ND 58105, USA Harris et al. 2003). In addition, it is considered a pest in 82 J Chem Ecol (2009) 35:81–95 many European countries (Barnes 1956). In common with pheromone extraction, coupled gas chromatographic– other species in the family Cecidomyiidae (gall midges), electroantennographic detection (GC–EAD) analyses, and Y- Hessian fly adults are short-lived, have a highly synchro- tube bioassays. Hessian flies used in the small-plot test were nized period of flight activity, and may be present in crops reared on hard red spring wheat, T. aestivum L. (genotype for brief periods of time only (Harris and Foster 1999). “Reeder”), in a greenhouse at North Dakota State University. Typically, outbreaks are sporadic, local, and difficult to These flies were also of the “Great Plains” biotype and predict (ibid.). As a consequence, Hessian flies are originated from approximately 5,000 puparia, obtained in normally discovered only after they have become a serious 2000, from the USDA-ARS laboratory at Purdue University. problem. Various methods are used to control Hessian flies Pheromone Extraction The pheromone gland in Hessian fly including delayed planting of winter wheat, use of resistant females is associated with the eighth and ninth abdominal wheat varieties, and application of broad-spectrum insecti- intersegmental membrane epidermis (Solinas and Isidoro cides (Buntin et al. 1992; El Bouhssini et al. 1999; Rausher 1996). Gland extracts were prepared by excising the 2001; Berzonsky et al. 2003). All of these methods might terminal abdominal segments of virgin calling females be improved by a sensitive method for the detection of early (Bergh et al. 1990; Foster et al. 1991a). Ovipositors were infestations (Buntin et al. 1990, 1992; Cox and Hatchett placed into a vial partially immersed in liquid nitrogen. 1986; Harris et al. 2003). One potential method for field When sufficient ovipositors (approximately 30) were monitoring might employ the use of sex pheromone-baited collected, the vial was allowed to warm to ambient traps (Harris and Foster 1999). Earlier work demonstrated temperature, and the tissue was extracted for 1–1.5 min in the presence of a sex pheromone in the Hessian fly (McKay distilled hexane (LabScan). Following extraction, the solvent and Hatchett 1984). One component of the female-produced was decanted into glass vials (2 ml) and stored at −18°C until sex pheromone, (2S,10E)-10-tridecen-2-yl acetate [2S-10E- use. All dissections were made between 09:00 and 11:30. 13:OAc], was identified (Foster et al. 1991b). However, when tested alone in a wind tunnel, this compound attracted GC–EAD Recordings GC–EAD (Arn et al. 1975) was used significantly fewer Hessian fly males than did female to analyze female gland extracts and synthetic compounds. extract (Harris and Foster, 1991). In a field study, traps A Hewlett-Packard 6890 GC (Palo Alto, CA, USA) with baited with the compound also failed to attract male flame ionization detection and an Innowax column (30 m× Hessian flies (Harris and Foster 1999). In the wind tunnel, 0.25 mm i.d., H-P), programmed from 80°C (held for male responses were tested to binary blends of 2S-10E-13: 2 min) to 220°C at 10°C/min, was used. Whole male bodies OAc and racemic mixtures of three other chemicals— were mounted in an antennal holder (JoAC, Lund, Sweden), (10Z)-10-tridecen-2-yl acetate, (10E)-10-tridecen-2-ol, and as described by Hillbur et al. (2001). Both antennae were tridec-2-yl acetate (Foster et al. 1991b; Harris and Foster exposed simultaneously to a charcoal-filtered and humidi- 1991)—found in female extract (Millar et al. 1991). fied air stream at a rate of approximately 0.3 m/s through a However, none of these blends attracted more males than glass tube (8-mm diameter). The signals from the antennae 2S-10E-13:OAc alone. In this study, we identified addi- were amplified (JoAC) before they were recorded and were tional compounds produced by female Hessian fly and analyzed with ElectroAntennoGraphy software (Syntech, formulated a blend that is attractive to male flies in the Hilversum, The Netherlands). field. Structure Elucidation Coupled GC–MS analyses of extracts of female Hessian fly were generally carried out Methods and Materials as described earlier (Hillbur et al. 2005). Separations were achieved with a 60 m, 0.25-mm i.d. fused silica capillary, Insect Rearing Wheat plants (Triticum aestivum L., genotype DB-5/MS (J&W Scientific, Folsom, CA, USA) under “Blueboy”) that contained Hessian fly puparia of the “Great temperature program: 3 min at 60°C, then programmed to Plains” biotype (provided by the US Department of 280°C at a rate of 5°C/min. An additional fused silica Agriculture-Agricultural Research Service (USDA-ARS) column, 50 m, 0.25 mm i.d., Permabond FFAP (Macherey and the Department of Entomology, Purdue University, West & Nagel, Düren, Germany), was also used. Lafayette, IN, USA) were put into Plexiglas cages (29×34× 29 cm) held in an environmental chamber (25°C, 70% relative Enantioselective GC was carried out with a 25 m, 0.25-mm humidity (RH) and 12:12 L:D photoperiod; lights on 09:00) at i.d. fused silica capillary coated with a 1:1 mixture of Alnarp, Sweden. Infested plants were watered daily to avoid heptakis 6-O-tert.butyldimethylsilyl-2,3-di-O-methyl β- desiccation of developing flies. Typically, adults emerged 7– cyclodextrin and OV 17 at 100°C isothermal and using 14 days later, and the sexes were separated and used for hydrogen as the carrier gas. J Chem Ecol (2009) 35:81–95 83 1H nuclear magnetic resonance (NMR) spectra of hepten-2-ol. Reaction with 3,4-dihydro-2H-pyran and synthetic compounds were recorded on a Bruker AMX-400 ozonization followed by reductive workup produced instrument (Karlsruhe, Germany) using tetramethylsilan (5S)-5-(2-tetrahydropyranyloxy)hexan-1-ol (VII) via the as the internal standard. protected alkenol VI. Transformation of the primary hydrox- yl group to the bromide VIII and chain elongation of its Syntheses If not otherwise stated, starting material, Grignard product with (2E,4E)-2,4-heptadien-1-yl acetate reagents, and solvents were purchased from Aldrich and (Samain et al.
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