JACEN  Vol.5 No.4 , November 2016
Synthesis of Southern Corn Rootworm Pheromone from S-Citronellol and Its Field Evaluation
Abstract: Southern rootworm (Diabrotica undecimpunctata howardi) affects several plants such as soybean, sorghum, wheat, cucumber, alfalfa, cucurbits and it is most damaging to corn and peanuts. The pheromone based “attract and kill” strategy is one of the powerful ways to control pest population. To address our key objective of the practical utility of the synthetic pheromone, we have developed a simple synthetic strategy to produce gram scale southern corn rootworm pheromone in nine simple steps starting from S-Citronellol. The present strategy takes advantage of the existing chiral center of commercially available S-Citronellol. To get the basic carbon skeleton of the pheromone, the main step in the synthetic strategy is coupling of aliphatic units through Wittig reaction. The phosphonium salt from a non-functionalized aliphatic bromide followed by Wittig reaction improved the overall yield in the multistep synthesis of this pheromone. The large-scale production of pheromone enabled us to test it in the field.
Cite this paper: Subramanian, T. , Webb, M. , Bhagavathy, G. , Rozek, A. , Paraselli, B. and Chauhan, K. (2016) Synthesis of Southern Corn Rootworm Pheromone from S-Citronellol and Its Field Evaluation. Journal of Agricultural Chemistry and Environment, 5, 223-230. doi: 10.4236/jacen.2016.54023.

[1]   Erbach, D.C. and Tollefson, J.J. (1983) Granular Insecticide Application for Corn Rootworm Control. Transactions of the ASAE, 26, 696-699.

[2]   Gogos, A., Knauer, K. and Bucheli, T.D. (2012) Nanomaterials in Plant Protection and Fertilization: Current State, Foreseen Applications, and Research Priorities. Journal of Agricultural and Food Chemistry, 60, 9781-9792.

[3]   Ferry, N., Edwards, M.G., Gatehouse, J., Capell, T., Christou, P. and Gatehouse, A.M.R. (2006) Transgenic Plants for Insect Pest Control: A Forward Looking Scientific Perspective. Transgenic Research, 15, 13-19.

[4]   Kabaluk, T.J., Lafontaine, J.P. and Borden, J.H. (2015) An Attract and Kill Tactic for Click Beetles Based on Metarhizium brunneum and a New Formulation of Sex Pheromone. Journal of Pest Science, 88, 707-716.

[5]   Guss, P.L., Tumlinson, J.H., Sonnet, P.E. and McLaughlin, J.R. (1983) Identification of a Female-Produced Sex Pheromone from the Southern Corn Rootworm. Diabrotica undecimpunctata howardi Barber. Journal of Chemical Ecololgy, 9, 1363-1375.

[6]   Enders, D. and Jandeleit, B. (1995) Efficient and Convergent Synthesis of (R)-(-)-10-Methyltridecan-2-One, the Sex-Pheromone of the Spotted Cucumber Beetle, by Iron-Mediated Chirality Transfer. Liebigs Annalen, 7, 1173-1176.

[7]   Shikichi, Y. and Mori, K. (2000) Metathesis-Mediated Synthesis of (R)-10-Methyl-2-Tride-canone, the Southern Corn Rootworm Pheromone. Bioscience Biotechnology and Biochemistry, 76, 407-409.

[8]   Oppolzer, W., Dudfield, P., Stevenson, T. and Godel, T. (1985) Camphor Sulfonamide-Shielded, Asymmetric 1,4-Additions and Enolate Alkylations; Synthesis of a Southern Corn Rootworm Pheromone. Helvetica Acta, 68, 212-215.

[9]   Shikichi, Y. and Mori, K. (2012) Synthesis of All the Stereoisomers of 6-Methyl-2-Octade-canone, 14-Methyl-2-Octadecanone, and 6,14-Dimethyl-2-Octadecanone, Sex Pheromone Components of the Lyclene Dharma Dharma Moth, from the Enantiomers of Citronellal. Bioscience Biotechnology and Biochemistry, 76, 1943-1951.

[10]   Senda, S. and Mori, K. (1983) Synthesis of (R)-(-)-10-Methyl-2-Tridecanone, the Pheromone of the Southern Corn Rootworm. Agricultural Biological Chemistry, 47, 795-798.

[11]   Ogura, T. and Usuki, T. (2013) Total Synthesis of Acetogenins E, G and K, and Centrolobol. Tetrahedron, 69, 2807-2815.

[12]   Odinokov, V.N., Kukovinets, O.S., Kasradze, V.G., Tsyglintseva, E.Yu., Serebryakov, E.P. and Tolstikov, G.A. (1992) Insect Pheromones and Their Analogues. xxxv. Synthesis of (r)-(-)-10-Methyltridecan-2-One—The Pheromone of Diabrotica undecimpunctata. Chemistry of Natural Compounds, 28, 106-109.