Identification of 1-methyloctyl butanoate as the major sex pheromone component from females of the saddle gall midge, Haplodiplosis marginata (Diptera: Cecidomyiidae)
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  • 作者:Florence Censier (1)
    Christophe Y. Fischer (2)
    Sandrine Chavalle (3)
    Stephanie Heuskin (2)
    Marie-Laure Fauconnier (4)
    Bernard Bodson (1)
    Michel De Proft (3)
    Georges C. Lognay (2)
    Pascal Laurent (4) (5)
  • 关键词:Haplodiplosis marginata ; Sex pheromone ; Alk ; 2 ; yl butanoates ; Chiral gas chromatography ; Pheromone synthesis ; Field ; trapping experiment
  • 刊名:Chemoecology
  • 出版年:2014
  • 出版时间:December 2014
  • 年:2014
  • 卷:24
  • 期:6
  • 页码:243-251
  • 全文大小:529 KB
  • 参考文献:1. Andersson MN, Haftmann J, Stuart JJ, Cambron SE, Harris MO, Foster SP, Franke S, Franke W, Hillbur Y (2009) Identification of sex pheromone components of the hessian fly, / Mayetiola destructor. J Chem Ecol 35:81鈥?5. doi:10.1007/s10886-008-9569-1 CrossRef
    2. Betts TJ (1996) Indications of the chemical structure of oxygen-containing constituents of volatile oils by capillary gas chromatography using one or two modified 尾- and 伪-cyclodextrin phases. J Chromatogr A 724:403鈥?10. doi:10.1016/0021-9673(95)00970-1 CrossRef
    3. Brat P, Brillouet JM, Reynes M, Cogat PO, Oll茅 D (2000) Free volatile components of passion fruit puree obtained by flash vacuum-expansion. J Agric Food Chem 48:6210鈥?214. doi:10.1021/jf000645i CrossRef
    4. Bruce TJA, Hooper AM, Ireland L, Jones OT, Martin JL, Smart LE, Oakley J, Wadhams LJ (2007) Development of a pheromone trap monitoring system for orange wheat blossom midge, / Sitodiplosis mosellana, in the UK. Pest Manag Sci 63:49鈥?6. doi:10.1002/ps.1307 CrossRef
    5. Censier F, Chavalle S, Wittouck D, De Proft M, Bodson B (2012) Chemical control of / Haplodiplosis marginata von Roser (Diptera: Cecidomyiidae). Commun Appl Biol Sci 77:667鈥?75
    6. Congiu R, Falconieri D, Marongiu B, Piras A, Porcedda S (2002) Extraction and isolation of / Pistacia lentiscus L. essential oil by supercritical CO2. Flavour Fragr J 17:239鈥?44. doi:10.1002/ffj.1095 CrossRef
    7. Cousin H, Peulon-Agasse V, Combret J-C, Cardinael P (2009) Mono-2, 3 or 6-hydroxy methylated 尾-cyclodextrin (Eicosa- / O-methyl-尾-cyclodextrin) isomers as chiral stationary phases for capillary GC. Chromatographia 69:911鈥?22. doi:10.1365/s10337-009-0955-9 CrossRef
    8. Cserhati T, Forgacs E (2001) Retention characteristics of a (2,3,6-tri- / O-methyl)-尾-cyclodextrin coated capillary column. Anal Lett 34:145鈥?53. doi:10.1081/AL-100002712 CrossRef
    9. De Clercq R, D鈥橦erde J (1972) Bijdrage tot de Studie van de Biologie, de verspreiding, de Pathogeniteit en de Bestrijding van de Tarwestengelgalmug / Haplodiplosis marginata (von Roser 1840) R眉bsaamen 1911. Rijkstation voor Nematologie en Entomologie, Merelbeke
    10. Dewar M (2012) Ecology and control of saddle gall midge, / Haplodiplosis marginata von Roser (Diptera, Cecidomyiidae). HGCA, Agriculture and Horticulture Development Board. http://publications.hgca.com/publications/documents/RR76.pdf. Accessed 3 Dec 2013
    11. Dublon IAN (2009) The aggregation pheromone of the western flower thrips. PhD thesis, University of Keele, UK
    12. Fischer CY, Lognay GC (2012) Simple and automatic closed grinding and extraction system. J Chem Educ 89:1611鈥?612. doi:10.1021/ed2007907
    13. Golightly WH, Woodville HC (1974) Studies of recent outbreaks of saddle gall midge. Ann Appl Biol 77:97鈥?01 CrossRef
    14. Gries R, Gries G, Khaskin G, King S, Olfert O, Kaminski LA, Lamb R, Bennett R (2000) Sex pheromone of orange wheat blossom midge, / Sitodiplosis mosellana. Naturwissenschaften 87:450鈥?54. doi:10.1007/s001140050757 CrossRef
    15. Hall DR, Farman DI, Cross JV, Pope TW, Ando T, Yamamoto M (2009) ( / S)-2-acetoxy-5-undecanone, female sex pheromone of the raspberry cane midge, / Resseliella theobaldi (Barnes). J Chem Ecol 35:230鈥?42. doi:10.1007/s10886-009-9588-6 CrossRef
    16. Hall DR, Amarawardana L, Cross JV, Francke W, Boddum T, Hillbur Y (2012) The chemical ecology of cecidomyiid midges (Diptera: Cecidomyiidae). J Chem Ecol 38:2鈥?2. doi:10.1007/s10886-011-0053-y CrossRef
    17. Hamilton JGC, Hall DR, Kirk WDJ (2005) Identification of a male-produced aggregation pheromone in the western flower thrips / Frankliniella occidentalis. J Chem Ecol 31:1369鈥?379. doi:10.1007/s10886-005-1351-z CrossRef
    18. Hillbur Y, El-Sayed A, Bengtsson M, L枚fqvist J, Biddle A, Plass E, Francke W (2000) Laboratory and field study of the attraction of male pea midges, / Contarinia pisi, to synthetic sex pheromone components. J Chem Ecol 26:1941鈥?952. doi:10.1023/A:1005557026246 CrossRef
    19. Hirata H, Mayama M, Miyagishi M (2002) Substrate-solvent dependence of enantioselectivity in porcine pancreatic lipase catalyzed transesterification between tributyrylglycerol and secondary alcohols in organic solvent. J Oleo Sci 51:539鈥?47. doi:10.5650/jos.51.539 CrossRef
    20. Ho H-Y, Millar JG (2002) Identification, electroantennogram screening, and field bioassays of volatile chemicals from / Lygus hesperus Knight (Heteroptera: Miridae). Zool Stud 41:311鈥?20
    21. Latteur G (1972) Importance des populations larvaires de la C茅cidomyie 茅questre ( / Haplodiplosis / marginata von Roser聽=聽 / H. equestris Wagner, Diptera, Cecidomyiidea) dans les froments des principales zones c茅r茅ali猫res du Sud de la Belgique en 1970 et 1971. Parasitica 28:16鈥?4
    22. Liu Y, He X-K, Hall DR, Farman D, Amarawardana L, Cross JV, Liu Q-R (2009) (2S,8Z)-2-butyroxy-8-heptadecene: major component of the sex pheromone of chrysanthemum gall midge, / Rhopalomyia longicauda. J Chem Ecol 35:715鈥?23 CrossRef
    23. Molinari F, Gandolfi R, Aragozzini F (1996) Microbial catalyzed esterification of primary and secondary alcohols in organic solvent. Biotechnol Tech 10:103鈥?08 CrossRef
    24. Nijveldt W, Hulshoff AJA (1968) Waarnemingen inzake de tarwestengelgalmug ( / Haplodiplosis / equestris Wagner) in Nederland. Centrum voor landbouwpublikaties en landbouwdokumentatie
    25. Skuhrav谩 M (2000) / Haplodiplosis / marginata. In: Papp L, Darvas B (eds) Contributions to a manual of palaearctic Diptera, vol 1., General and applied dipterologyScience Herald, Budapest, pp 588鈥?89
    26. Skuhrav媒 V, Skuhrav谩 M, Brewer JW (1983) Ecology of the saddle gall midge / Haplodiplosis / marginata (von Roser) (Diptera, Cecidomyiidae). Zeitschrift f眉r Angewandte Entomologie 96:476鈥?90 CrossRef
    27. Skuhrav媒 V, Skuhrav谩 M, Brewer JW (1993) The saddle gall midge / Haplodiplosis marginata (Diptera: Cecidomyiidae) in Czech Republic and Slovak Republic from 1971鈥?989. Acta Soc Zool Bohem 57:111鈥?37
    28. Strohalm H, Dregus M, Wahl M, Engel K-H (2007) Enantioselective analysis of secondary alcohols and their esters in purple and yellow passion fruits. J Agric Food Chem 55:10339鈥?0344. doi:10.1021/jf072464n CrossRef
    29. Strohalm H, Dold S, Pendzialek K, Weiher M, Engel K-H (2010) Preparation of passion fruit-typical 2-alkyl ester enantiomers via lipase-catalyzed kinetic resolution. J Agric Food Chem 58:6328鈥?333. doi:10.1021/jf100432s CrossRef
    30. Van den Dool H, Kratz PD (1963) A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography. J Chromatogr 11:463鈥?71 CrossRef
    31. van Ruth SM, Grossmann I, Geary M, Delahunty CM (2001) Interactions between artificial saliva and 20 aroma compounds in water and oil model systems. J Agric Food Chem 49:2409鈥?413. doi:10.1021/jf001510f CrossRef
    32. Wang Y, Finn C, Qian MC (2005) Impact of growing environment on chickasaw blackberry (Rubus L.) aroma evaluated by gas chromatography olfactometry dilution analysis. J Agric Food Chem 53:3563鈥?571. doi:10.1021/jf048102m CrossRef
    33. Witzgall P, Bengtsson M, Unelius CR, Lofqvist J (1993) Attraction of the pea moth / Cydia nigricana F. (Lepidoptera: Tortricidae) to female sex pheromone (E, E)-8,10-dodecadien-1-yl acetate is inhibited by geometric isomers E, Z, Z, E and Z. Z. J Chem Ecol 19:1917鈥?928 CrossRef
  • 作者单位:Florence Censier (1)
    Christophe Y. Fischer (2)
    Sandrine Chavalle (3)
    Stephanie Heuskin (2)
    Marie-Laure Fauconnier (4)
    Bernard Bodson (1)
    Michel De Proft (3)
    Georges C. Lognay (2)
    Pascal Laurent (4) (5)

    1. Crops Management Unit, Gembloux Agro-Bio Tech, University of Liege, Passage des D茅port茅s 2, 5030, Gembloux, Belgium
    2. Laboratory of Analytical Chemistry, Gembloux Agro-Bio Tech, University of Liege, Passage des D茅port茅s 2, 5030, Gembloux, Belgium
    3. Plant Protection and Ecotoxicology Unit, Life Sciences Department, Walloon Agricultural Research Centre, Balachowsky Building, Chemin de Liroux 2, 5030, Gembloux, Belgium
    4. General and Organic Chemistry Unit, Gembloux Agro-Bio Tech, University of Liege, Passage des D茅port茅s 2, 5030, Gembloux, Belgium
    5. Unit of General Chemistry, Universit茅 Libre de Bruxelles, Route de Lennik, 808 CP 609, 1070, Brussels, Belgium
  • ISSN:1423-0445
文摘
The saddle gall midge, Haplodiplosis marginata (von Roser) (Diptera: Cecidomyiidae), has undergone a resurgence recently as a pest of cereals in Belgium and other European countries. An effective monitoring tool of saddle gall midge flights is needed to understand the enigmatic population dynamics of this pest, and to design an integrated management strategy. Therefore, volatile compounds emitted by females (alkan-2-ols and alk-2-yl butanoates) were identified, and the chirality of the emitted esters was determined to be the R absolute configuration. In field-trapping experiments, racemic non-2-yl butanoate attracted substantial numbers of H. marginata males. Thus, this compound will be useful in baited traps for monitoring seasonal flight patterns, and improving integrated management of the saddle gall midge in agricultural systems.
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