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Identification of a Novel Moth Sex Pheromone Component from Chilecomadia valdiviana

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Abstract

Chilecomadia valdiviana (Philippi) (Lepidoptera: Cossidae) is an insect native to Chile. The larval stages feed on the wood of economically important fruit tree species such as apple, pear, olive, cherry, and avocado, and also on eucalyptus. This causes weakening and, in case of severe infestation, death of the tree. We report identification of the sex pheromone produced by females of this species. Hexane extracts of the abdominal glands of virgin females were analyzed by gas chromatography (GC) with electroantennographic detection, GC coupled with mass spectrometry, and GC coupled to infrared spectroscopy. The major pheromone component was identified as (7Z,10Z)-7,10-hexadecadienal (Z7,Z10–16:Ald), and minor components present in the extracts were (Z)-7-hexadecenal and (Z)-9-hexadecenal, hexadecanal, and (9Z,12Z)-9,12-octadecadienal. Structural assignments were carried out by comparison of analytical data of the natural products and their dimethyl disulfide adducts with those of authentic reference samples. In field tests, traps baited with Z7,Z10–16:Ald captured significantly more males than control traps.

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References

  • Ando T, Inomata S-J, Yamamoto M (2004) Lepidopteran sex pheromones. Top Curr Chem 239:51–96

    Article  CAS  PubMed  Google Scholar 

  • Angulo AO, Olivares TS (1991) Chilecomadia valdiviana (Philippi) (Lepidoptera: Cossidae) asociado a Ulmus glabra Hudson forma pendula (Laud.) Rehder (“Olmo pendula”) en la VIII Región (Concepción, Chile). Bosque 12:67–68

    Article  Google Scholar 

  • Angulo AO, Olivares TS (2008) Catálogo crítico e ilustrado de los Cossidae de Chile (Lepidoptera: Cossidae). Lepidoptera Novae 1:119–133

    Google Scholar 

  • Artigas JN (1994) Entomología Económica. Insectos de interés agrícola, forestal, médico y veterinario. Vol. 2. Ediciones Universidad de Concepción, Chile, pp. 479–486

  • Bestmann HJ, Stransky W, Vostrowsky O (1976) Darstellung lithiumsalzfreier Ylidlösungen mit Natrium-bis(trimethylsilyl)amid als base. Chem Ber 109:1694–1700

    Article  CAS  Google Scholar 

  • Bouwer MC, Slippers B, Degefu D, Wingfield MJ, Lawson S, Rohwer ER (2015) Identification of the sex pheromone of the tree infesting cossid moth Coryphodema tristis (Lepidoptera: Cossidae). PLoS One 10:e0118575

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Buser H-R, Arn H, Guerin P, Rauscher S (1983) Determination of double bond position in mono-unsaturated acetates by mass spectrometry of dimethyl disulfide adducts. Anal Chem 55:818–822

    Article  CAS  Google Scholar 

  • Capizzi A, Tonini C, Arsura E, Guglielmetti G, Massardo P, Piccardi P (1983) Sex pheromone components of the European goat moth, Cossus cossus. J Chem Ecol 9:191–200

    Article  CAS  PubMed  Google Scholar 

  • Carballeira NM, Shalabi F, Cruz C (1994) Thietane, tetrahydrothiophene and tetrahydrothiopyran formation in reaction of methylene-interrupted dienoates with dimethyl disulfide. Tetrahedron Lett 35:5575–5578

    Article  CAS  Google Scholar 

  • Cerda LA, Lewis PD (1993) Estudio y seguimiento del taladrador de la Madera Chilecomadia valdiviana (Lep.: Cossidae) en plantaciones de Eucalyptus nitens y E. delegatensis en el predio Santa Luisa de Forestal Rio Vergara S.A., in: Barros Asenjo S, Prado JD, Alvear CS (eds.), Actas Simposio Los Eucaliptos en el Desarrollo Forestal de Chile Instituto Forestal, Santiago pp. 339–353

  • Cerda L, Angulo A, Durán A, Olivares T (2000) Insectos asociados a bosques del centro sur de Chile. In: Baldini A, Pancel L (eds) . Agentes de daño en el bosque nativo Editorial Universitaria, Santiago de Chile, pp. 201–281

    Google Scholar 

  • Chen X, Nakamuta K, Nakanishi T, Nakashima T, Tokoro M, Mochizuki F, Fukumoto T (2006) Female sex pheromone of a carpenter moth, Cossus insularis (Lepidoptera: Cossidae). J Chem Ecol 32:669–679

    Article  CAS  PubMed  Google Scholar 

  • Corey EJ, Schmidt G (1979) Useful procedures for the oxidation of alcohols involving pyridinium dichromate in aprotic media. Tetrahedron Lett 5:399–402

    Article  Google Scholar 

  • Degefu DT, Hurley BP, Garnas J, Wingfield MJ, Ahumada R, Slippers B (2013) Parallel host range expansion in two unrelated cossid moths infesting Eucalyptus nitens on two continents. Ecol Entomol 38:112–116

    Article  Google Scholar 

  • El-Sayed AM (2014) The Pherobase: Database of pheromones and semiochemicals <http://www.pherobase.com>

  • Fang Y-L, Sun J-H, Zhao C-H, Zhang Z-N (2005) Sex pheromone components of the sandthorn carpenterworm Holcocerus hippophaecolus. J Chem Ecol 31:39–48

    Article  CAS  PubMed  Google Scholar 

  • Gebeyehu S, Hurley BP, Wingfield MJ (2005) A new lepidopteran insect pest discovered on commercially grown Eucalyptus nitens in South Africa. S Afr J Sci 101:26–28

    CAS  Google Scholar 

  • Gentili P (1988) Análisis de la distribución geográfica de Cossidae (Lepidoptera: Ditrysia) de la Patagonia andina. Rev Chil Hist Nat 61:191–198

  • Gentili P (1989) Revisión sistemática de los Cossidae (Lep.) de la Patagonia Andina. Revista de la Sociedad Entomológica Argentina 45:1–75

    Google Scholar 

  • Hall DR, Amarawardana L, Cross JV, Francke W, Boddum T, Hillbur Y (2012) The chemical ecology of cecidomyiid midges (Diptera: Cecidomyiidae). J Chem Ecol 38:2–22

    Article  CAS  PubMed  Google Scholar 

  • Hegazi E, Khafagi WE, Konstantopoulou M, Raptopoulos D, Tawfik H, Abd El-Aziz GM, Abd El-Rahman SM, Atwa A, Aggamy E, Showeil S (2009) Efficient mass-trapping method as an alternative tactic for suppressing populations of leopard moth (Lepidoptera: Cossidae). Ann Entomol Soc Am 102:809–818

    Article  Google Scholar 

  • Hezagi EM, Khafagi WE, Konstantopoulou M, Schlyter F, Raptopoulos D, Shweil S, Abd El-Rahman S, Atwa A, Ali SE, Tawfik H (2010) Suppression of leopard moth (Lepidoptera: Cossidae) populations in olive trees in Egypt through mating disruption. J Econ Entomol 103:1621–1627

    Article  Google Scholar 

  • Hill AS, Roelofs WL (1981) Sex pheromone of the saltmarsh caterpillar moth, Estigmene acrea. J Chem Ecol 7:655–668

    Article  CAS  PubMed  Google Scholar 

  • Hill AS, Kovalev BG, Nikolaeva LN, Roelofs WL (1982) Sex pheromone of the fall webworm moth, Hyphantria cunea. J Chem Ecol 8:383–396

    Article  CAS  PubMed  Google Scholar 

  • Ho HY, Tao YT, Tsai RS, Wu YL, Tseng HK, Chow YS (1996) Isolation, identification, and synthesis of sex pheromone components of female tea cluster caterpillar, Andraca bipunctata Walker (Lepidoptera: Bombycidae) in Taiwan. J Chem Ecol 22:271–285

    Article  CAS  PubMed  Google Scholar 

  • Horner L, Oediger H, Hoffmann H (1959) Reaktionen mit Triphenylphosphin-Dihalogeniden. Liebigs Ann Chem 626:26–34

    Article  CAS  Google Scholar 

  • Jing X, Zhang J, Luo Y, Zong S, Liu P, Jia J (2010) Identification and field evaluation of the female sex pheromone of the sand Salix carpenterworm Holcocerus arenicola Staudinger (Lepidoptera: Cossidae). Z Naturforsch 65c:403–411

  • Jintong Z, Yan H, Xianzuo M (2001) Sex pheromone of the carpenterworm, Holcocerus insularis (Lepidoptera, Cossidae). Z Naturforsch 56c:423–429

  • Kliejunas JT, Tkacz BM, Burdsall HH Jr, Denitto GA, Eglitis A, Haugen DA, Wallner WE (2001) Pest risk assessment of the importation into the United States of unprocessed eucalyptus logs and chips from South America. Gen. TeC. Rep. FPL-GTR-124. Madison, WI: U.S. Department of Agriculture, Forest Service, Forest products Laboratory 134 p

  • Malosse C, Descoins C, Frerot B (1993) Identification of a minor component of the sex pheromone of the leopard moth (Zeuzera pyrina L.; Lepidoptera, Cossidae) by capillary gas chromatography. J High Resolut Chromatogr 16:123–125

    Article  CAS  Google Scholar 

  • Nakanishi T, Nakamuta K, Mochizuki F, Fukumoto T (2013) Mating disruption of the carpenter moth, Cossus insularis (Staudinger) (Lepidoptera: Cossidae) with synthetic sex pheromone in Japanese pear orchards. J Asia Pac Entomol 16:251–255

    Article  CAS  Google Scholar 

  • Nishiguchi T, Hayakawa S, Hirasaka Y, Saitoh M (2000) Selective monotetrahydropyranylation of 1,n-diols catalyzed by aqueous acids. Tetrahedron Lett 9843–9846

  • Olivares TS, Rodríguez MA, Angulo AO (2010) Un nuevo género, nuevas especies y nuevos registros de nóctuidos alto andinos IV (Lepidoptera: Noctuidae). SHILAP-Rev Lepidopt 38:139–151

    Google Scholar 

  • Pasqualini E, Antropoli A, Faccioli B (1992) Attractant performance of a synthetic sex pheromone for Zeuzera pyrina L. (Lepidoptera; Cossidae). Bollettino dell’Istituto di Entomologia “Guido Grandi” della Universita degli Studi di Bologna 46:101–108

  • Pasqualini E, Antropoli A, Faccioli G, Molfese M (1993) Zeuzera pyrina L. (Lepidoptera; Cossidae): Results of five year researches on sex attractant. Bulletin IOBC-WPRS 16:189–194

    Google Scholar 

  • Pasqualini E, Natale D, Witzgall P, El-Sayed A (1999) Zeuzera pyrina and Cossus cossus (Lepidoptera; Cossidae) control by pheromones: four years advances in Italy. Bulletin IOBC-WPRS 22:115–124

    Google Scholar 

  • Persoons CJ, Voerman S, Verwiel PEJ, Ritter FJ, Nooyen WJ, Minks AK (1976) Sex pheromone of the potato tuberworm moth, Phthorimaea operculella: isolation, identification and field evaluation. Entomol Exp Appl 20:289–300

    Article  CAS  Google Scholar 

  • Persoons CJ, Vos JD, Yadav JS, Prasad AR, Sighomony S, Jyothi KN, Prasuna AL (1993) Indo-Dutch cooperation on pheromones of Indian agricultural pest insects: Sex pheromone components of Diacrisia obliqua (Arctiidae), Achaea janata (Noctuidae) and Amsacta albistriga (Arctiidae). Bulletin IOBC-WPRS 16:136–140

    Google Scholar 

  • Petersen JG (1988) Chilecomadia valdiviana (Philippi) (Lepidoptera: cossidae), asociado a Nothofagus pumilio (Poepp. et Endl) Krasser (Lenga) en la Región de Magallanes. Anales del Instituto de la Patagonia 18:51–55

  • Prado E (1991) Artrópodos y sus enemigos naturales asociados a plantas cultivadas en Chile. Boletín Técnico N° 169, Instituto de Investigaciones Agropecuarias, La Platina, 203 p

  • Ripa R, Larral P (eds) (2008) Manejo de plagas en paltos y cítricos, Colección Libros INIA N°, vol 23. La Cruz, Chile

    Google Scholar 

  • Schoorl JW (1990) A phylogenetic study of Cossidae based on external adult morphology. Zoologische Verhandelingen 263:1–295

    Google Scholar 

  • Siegel S, Castellan NJ (1988) Nonparametric statistics for behavioral sciences. McGraw-Hill, New York, 399 pp

  • Sokal RR, Rohlf FJ (1995) Biometry: The principles and practice of statistics in biological research. W.H. Freeman, New York, 937 p

  • Szöcs G, Tóth M, Kárpáti Z, Zhu J, Löfstedt C, Plass E, Francke W (2004) Identification of polyene hydrocarbons from the northern winter moth Operophtera fagata, and development of a specific lure for pheromone traps. Chemoecology 14:985–100

    Article  CAS  Google Scholar 

  • Tonini C, Cassani G, Massardo P, Guglielmetti G, Castellari PL (1986) Study of female sex pheromone of leopard moth, Zeuzera pyrina L Isolation and identification of three components. J Chem Ecol 12:1545–1558

    Article  CAS  PubMed  Google Scholar 

  • Ureta RE (1957) Revisión de la Familia Cossidae (Lep. Het.) en Chile. Bol Mus Nac Hist Nat 27:127–153

    Google Scholar 

  • Vincenti M, Guglielmetti G, Cassani G, Tonini C (1987) Determination of double bond position in diunsaturated compounds by mass spectrometry of dimethyl disulfide derivatives. Anal Chem 59:694–699

    Article  Google Scholar 

  • Wiley GA, Hershkowitz RL, Rein BM, Chung BC (1964) Studies in organophosphorus chemistry. I Conversion of alcohols and phenols to halides by tertiary phosphine dihalides. J Am Chem Soc 86:964–965

    Article  CAS  Google Scholar 

  • Yang M, Zhang J, Zong S, Luo Y, Cao C, Fan L, Liu H, Xin H (2012) Synthesis and field evaluation of sex attractants of Holcocerus vicarius (Lepidoptera: Cossidae). Sci Silvae Sin 48:61–66

    CAS  Google Scholar 

  • Yang M-H, Liu H-X, Liu J-L, Jing X-Y, Zhang J-T, Fan L-H, Wang S-F (2015) Sex pheromone components of the carpenterworm moth, Holcocerus vicarius. Entomol Exp Appl 154:199–205

    Article  CAS  Google Scholar 

  • Zhang J, Jing X, Luo Y, Li Z, Zong S, Yang M (2009) The sex pheromone of the sand sagebrush carpenterworm, Holcocerus artemisiae (Lepidoptera, Cossidae). Z Naturforsch 64c:590–596

  • Zhang J, Liu H, Zhao W, Liu J, Zhong S (2011) Identification of the sex pheromone of Isoceras sibirica Alpheraky (Lepidoptera, Cossidae). Z Naturforsch 66c:527–533

Download references

Acknowledgments

Financial support from Fondo Nacional de Desarrollo Científico y Tecnológico (Fondecyt grant 1140779 to JB), Fondo de Equipamiento Científico y Tecnológico (Fondequip grant EQM130154), and from Deutscher Akademischer Austauschdienst (via material resources program to JB) is gratefully acknowledged. HH likes to thank the Comisión Nacional de Investigación Científica y Tecnológica (Conicyt) for a doctoral fellowship.

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Authors and Affiliations

  1. Instituto de Química, Pontificia Universidad Católica de Valparaíso, Valparaíso, Chile

    Heidy Herrera, M. Fernanda Flores, Francisca Santis & Jan Bergmann

  2. Millennium Nucleus Center in Molecular Ecology and Evolutionary Applications in the Agroecosystems (CEM), Facultad de Ciencias Agrarias, Universidad de Talca, Talca, Chile

    Wilson Barros-Parada & Eduardo Fuentes-Contreras

  3. Institute of Organic Chemistry, University of Hamburg, Hamburg, Germany

    Wittko Francke

  4. Departamento de Zoología, Facultad de Ciencias Naturales y Oceanográficas, Universidad de Concepción, Concepción, Chile

    Marcela Rodriguez

  5. Departamento de Química, Universidade Federal do Paraná, Curitiba, Brazil

    Paulo H. G. Zarbin

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  1. Heidy Herrera
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  2. Wilson Barros-Parada
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  3. M. Fernanda Flores
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Correspondence to Jan Bergmann.

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Herrera, H., Barros-Parada, W., Flores, M.F. et al. Identification of a Novel Moth Sex Pheromone Component from Chilecomadia valdiviana . J Chem Ecol 42, 908–918 (2016). https://doi.org/10.1007/s10886-016-0761-4

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