Evaluation of a Synthetic Pheromone Dispensers to Control the Potato Moth, Tecia Solanivora (Lepidoptera: Gelechiidae)

International Journal of Applied Chemistry

© 2019 by SSRG - IJAC Journal

Volume 6 Issue 1

Year of Publication : 2019

Authors : V.Vidal Medina, D.Peña Solorzano, C.Sierra Ávila and A.Romero-Frías

10.14445/23939133/IJAC-V6I1P105

How to Cite?

V.Vidal Medina, D.Peña Solorzano, C.Sierra Ávila and A.Romero-Frías, "Evaluation of a Synthetic Pheromone Dispensers to Control the Potato Moth, Tecia Solanivora (Lepidoptera: Gelechiidae)," SSRG International Journal of Applied Chemistry, vol. 6,  no. 1, pp. 28-36, 2019. Crossref, https://doi.org/10.14445/23939133/IJAC-V6I1P105

Abstract:

The synthesis of biologically active natural compounds like (E)-3-dodecenyl acetate from the Tecia solanivora Polvony, constitute an important step for the biological control of this pest, especially in undeveloped countries.
The sex pheromone produced by virgin female Tecia solanivora moths contains 98%
(E)-3-dodecenyl acetate and 2% of the Z isomer. An efficient three-step synthesis of (E)-3-dodecenyl acetate and its Z isomer as a byproduct is described. The synthetic route comprises the stereoselective formation of the E3 double bond by a modified Knoevenagel condensation, followed by a reduction of the carboxylic acid and finally the ester formation by acylation of the (E)-3-dodecenol intermediate. A complete structural characterization of the intermediates and final products, the overall yield was 59%, with a stereochemical purity for the target acetate of 98%.
The performance of dispensers loaded with the synthetic sex pheromone of potato moths, Tecia solanivora, was compared with a commercial dispenser under laboratory conditions.
In the field, data recorded included males captured in traps baited with synthetic pheromone. Male T. solanivora attraction to the synthetic pheromone polymeric dispensers was almost completely achieved over the course of 1 month, demonstrating its potential use for the control of this economically important insect pest in Colombia.

Keywords:

Tecia solanivora, synthetic pheromone, polymeric dispensers.

References:

[1] F. Bosa, T. Fukumoto, and N. Barreto, “Evaluación de la técnica de la interrupción de la cópula de Tecia solanivora Povolny (Lepidoptera: Gelechiidae),” Revista Colombiana de Entomología, vol. 31, no. 2, pp. 145-150, 2005.
[2] C. Felipe Bosa, A. M. Cotes Prado, T. Fukumoto, M. Bengtsson, and P. Witzgall, “Pheromone‐mediated communication disruption in Guatemalan potato moth, Tecia solanivora,” Entomologia experimentalis et applicata, vol. 114, no. 2, pp. 137-142, 2005.
[3] P. Karlson, and A. Butenandt, “Pheromones (ectohormones) in insects,” Annual review of entomology, vol. 4, no. 1, pp. 39-58, 1959.
[4] T. Ando, and R. Yamakawa, “Analyses of lepidopteran sex pheromones by mass spectrometry,” TrAC Trends in Analytical Chemistry, vol. 30, no. 7, pp. 990-1002, 2011.
[5] B. F. Nesbitt, P. S. Beevor, A. Cork, D. R. Hall, R. M. Murillo, and H. R. Leal, “Identification of components of the female sex pheromone of the potato tuber moth, Scrobipalpopsis solanivora,” Entomologia experimentalis et applicata, vol. 38, no. 1, pp. 81-85, 1985.
[6] C. Y. Yang, J. K. Jung, K. S. Han, K. S. Boo, and M. S. Yiem, “Sex pheromone composition and monitoring of the oriental fruit moth, Grapholita molesta (Lepidoptera: Tortricidae) in Naju pear orchards,” Journal of Asia-Pacific Entomology, vol. 5, no. 2, pp. 201-207, 2002.
[7] V. Ragoussis, E. Vamvaka, and M. Kolymbadi, “Short and stereoselective synthesis of (E)-3-alkenyl acetates, insect sex pheromone constituents of Lepidoptera; Gelechidae,” Journal of Chemical Research, vol. 2002, no. 8, pp. 398-399, 2002.
[8] M. Adinolfi, G. Barone, A. Iadonisi, and M. Schiattarella, “An easy approach for the acetylation of saccharidic alcohols. Applicability for regioselective protections,” Tetrahedron letters, vol. 44, no. 25, pp. 4661-4663, 2003.
[9] B. Czarnobai De Jorge, R. Bisotto‐de‐Oliveira, C. N. Pereira, and J. Sant'Ana, “Novel nanoscale pheromone dispenser for more accurate evaluation of Grapholita molesta (Lepidoptera: Tortricidae) attract‐and‐kill strategies in the laboratory,” Pest management science, vol. 73, no. 9, pp. 1921-1926, 2017.
[10] R. Bisotto-De-Oliveira, R. M. Morais, I. Roggia, S. J. Silva, J. SANT’ANA, and C. N. Pereira, “Polymers nanofibers asvehicles for the release of the synthetic sex pheromone of Grapholita molesta (Lepidoptera, Tortricidae),” Revista Colombiana de Entomología, vol. 41, no. 2, pp. 262-269, 2015.
[11] E. G. Brockerhoff, D. M. Suckling, M. Kimberley, B. Richardson, G. Coker, S. Gous, J. L. Kerr, D. M. Cowan, D. R. Lance, and T. Strand, “Aerial application of pheromones for mating disruption of an invasive moth as a potential eradication tool,” PLoS One, vol. 7, no. 8, pp. e43767, 2012.
[12] L. Stelinski, A. Il’Ichev, and L. Gut, “Efficacy and release rate of reservoir pheromone dispensers for simultaneous mating disruption of codling moth and oriental fruit moth (Lepidoptera: Tortricidae),” Journal of economic entomology, vol. 102, no. 1, pp. 315-323, 2009.
[13] G. P. Svensson, C. Liedtke, E. Hedenström, P. Breistein, J. Bång, and M. C. Larsson, “Chemical ecology and insect conservation: optimising pheromone-based monitoring of the threatened saproxylic click beetle Elater ferrugineus,” Journal of Insect Conservation, vol. 16, no. 4, pp. 549-555, 2012.
[14] A. Cork, K. De Souza, D. Hall, O. Jones, E. Casagrande, K. Krishnaiah, and Z. Syed, “Development of PVC-resin-controlled release formulation for pheromones and use in mating disruption of yellow rice stem borer, Scirpophaga incertulas,” Crop protection, vol. 27, no. 2, pp. 248-255, 2008.
[15] H. Zhu, H. W. Thistle, C. M. Ranger, H. Zhou, and B. L. Strom, “Measurement of semiochemical release rates with a dedicated environmental control system,” biosystems engineering, vol. 129, pp. 277-287, 2015.
[16] A. B. Attygalle, G. N. Jham, A. Svatoš, R. T. Frighetto, F. A. Ferrara, E. F. Vilela, M. A. Uchôa-Fernandes, and J. Meinwald, “(3E, 8Z, 11Z)-3, 8, 11-Tetradecatrienyl acetate, major sex pheromone component of the tomato pest Scrobipalpuloides absoluta (Lepidoptera: Gelechiidae),” Bioorganic & medicinal chemistry, vol. 4, no. 3, pp. 305-314, 1996.
[17] D. F. R. Rueda, and A. López-Ávila, “Dimorfismo sexual en pupas de Tecia solanivora (Povolný)(Lepidoptera: Gelechiidae),” Corpoica. Ciencia y Tecnología Agropecuaria, vol. 5, no. 1, pp. 41-42, 2004.
[18] N. Ragoussis, and V. Ragoussis, “Improvement on the synthesis of (E)-alk-3-enoic acids,” Journal of the Chemical Society, Perkin Transactions 1, no. 21, pp. 3529-3534, 1998.
[19] V. Ragoussis, M. Panopoulou, and N. Ragoussis, “Concise preparation of the (3 E, 5 Z)-alkadienyl system. New approach to the synthesis of principal insect sex pheromone constituents,” Journal of agricultural and food chemistry, vol. 52, no. 16, pp. 5047-5051, 2004.
[20] G. Angeli, G. Anfora, M. Baldessari, G. Germinara, F. Rama, A. De Cristofaro, and C. Ioriatti, “Mating disruption of codling moth Cydia pomonella with high densities of Ecodian sex pheromone dispensers,” Journal of applied entomology, vol. 131, no. 5, pp. 311-318, 2007.
[21] D. Povolný, “The Guatemalan potato tuber moth (Scrobipalpopsis solanivora Povolný, 1973) before the gateways of Europe (Lepidoptera, Gelechiidae),” Acta Universitatis Agriculturae et Silviculturae Mendelianae Brunensis, vol. 52, no. 1, pp. 183-196, 2015.
[22] I. Zenkevich, “Chromatographic identification of (E)-and (Z)-isomers of unsaturated organic compounds using their physicochemical characteristics,” Russian Journal of General Chemistry, vol. 83, no. 4, pp. 679-690, 2013.
[23] P. Calvert, and N. Billingham, “Loss of additives from polymers: a theoretical model,” Journal of Applied Polymer Science, vol. 24, no. 2, pp. 357-370, 1979.
[24] A. E. Imel, “Polymer Additives Effects on Structure and Dynamics,” 2015.
[25] S. Welter, C. Pickel, J. Millar, F. Cave, R. Van Steenwyk, and J. Dunley, “Pheromone mating disruption offers selective management options for key pests,” California agriculture, vol. 59, no. 1, pp. 16-22, 2005.