Nashrieh Shimi va Mohandesi Shimi Iran

Nashrieh Shimi va Mohandesi Shimi Iran

An improved synthesis of the sex pheromone of sugarcane borer, Sesamia cretic, as an intermediate of Zeuzera pyrina pheromone using a safe and economically efficient method

Document Type : Research Article

Authors
seyed ali tabatabaei ghomi
mehdi naseri
roya akbarzadeh
Academic Center for Education, Culture and Research, University of Tehran. IRAN
Abstract
In recent years, usage of sex pheromones as a replacement for pesticides against harmful insects has gained great interest due to their important ecological advantages like high specificity, biodegradability and low toxicity. The stem borer, Sesamia cretica Lederer (Lepidoptera, Noctuidae, Amphipyrinae), is one of the main insect pests of sorghum, maize, sugarcane, and cereal crops in the Mediterranean area. The components of sex pheromone of this insect was identified as consisting of (Z)-9-tetradecen-1-ol (80%), (Z)-9-tetradecen-1-yl acetate (10%), and (Z)-11-hexadecen-1-ol (10%). The previous reports for the synthesis of these compounds suffer from several problems such as difficult procedure, harmful solvents and low overall yields. in this research an efficient strategy for the synthesis of the main component of this pheromone is described from safe and readily available starting materials.
Keywords
sex pheromones
Sesamia cretica Lederer
(Z)-9-tetradecen-1-ol
synthesis
efficient strategy

Subjects

[1] Oxana V., Kharissova N., Boris I., César M., González O., Peña Y., Greener Synthesis of Chemical Compounds and Materials, Royal soc. Open sci., 6: 191378-191419 (2019).
[2] Mushta A., Zaki H., Mudasir A., Pheromones in Lepidopteran Insects: Types, Production, Reception and its Application  J. Pharm. and Phytochem. 6(7): 2552-2558 (2017).
] 3 [امانی، حسین.، حسنخواه، امیر.، طالب­نیا، فرید.، استخراج سلولز و بررسی تولید کربوکسی متیل سلولز از چند منبع ضایعاتی کشاورزی، نشریه شیمی و مهندسی شیمی ایران، (2)35: 113 تا 120 (1395).
[4] Anglade P., Balachowsky A. S., “Les Sesamia”, (ed) Appliquée 00E0; I'Agriculture, Tome II. Lepidoptères, 2ème vol. Masson et Cie, Paris (1972).
[5] Carde R. T., “Insect Pheromone Research: New Directions”, Chapman and Hall, New York (1996).
[6] Avand-Faghih A., Freerot B., Identification of the Sex Pheromone of Sesamia Cretica Lederer, J. Chem. Ecol., 34(1): 103-106 (2008).
[7] Avand-Faghih A., Zahdi H., Jafarloo M., Efficiency of Mating Disruption for Controlling the Leopard Moth, Zeuzera Pyrina L. (Lep.: Cossidae), in Walnut Orchards, J. Entomol. Soc. Iran (JESI), 35(2): 37-48 (2015).
[8] Pasqualini E., Vergnani S., Natale D., Accinelli G., IPM Improvement on Pome Fruit Orchards in Emilia-Romagna, Integrated Plant Protection in Orchards IOBC/wprs Bulletin, 22(6): 111-120 (1997).
[9] Voerman S., Persoons C. J., Priesner E., Sex Attractant for Currant Clearwing Moth Synanthedon Tipuliformis (Clerck) (Lepidoptera: Sesiidae), J. Chem. Ecol., 10: 1371-1376 (1984).
[10] Ishmuratov G., Yakovleva M. P., A Versatile Approach to the Synthesis of 9(Z)-Unsaturated Acyclic Insect Pheromones From Undec-10-Enoic Acid, Russ. Chem. Bull., 47: 1595–1597 (1997).
[11] Capdevila A., Prasad A. R., A Convergent and Highly Efficient Synthesis of (E,Z)-2,13-Octadecadienyl Acetate and (E,Z)-3,13-Octadecadienyl Acetate, Components of the Sex Pheromone of the Leopard Moth Zeuzera Pyrina, Through Sulfones, Org. Lett., 1(6): 845–848 (1999).
[12] Uchida M., Mori K., Matsu M., Synthesis of (Z,Z)-3,13-Octadecadienyl Acetate and its (E,Z)-Isomer, the Attractant for the Cherry Tree Borer, Agric. Biol. Chem., 42: 1067-1070 (1978).
[13] Xue-Hai Z., Guang-Zhong G., Guo-Qiang L., Yuan-Wei W., Pei-Heng W., Zhen-Yu L., Studies on Identification and Syntheses of Insect Pheromones XXII : Sex Pheromone of Poplar Twig Clearwing Mothparanthrene Tabaniformis Rott-Structure and Synthesis, J. Chem. Ecol., 12(6): 1263-1271 (1986).
[14] Naka H., Nakazawa T., Sugie M., Synthesis and Characterization of 3,13- and 2,13-Octadecadienyl Compounds for Identification of the Sex Pheromone Secreted by a Clearwing Moth, Nokona Pernix, Biosci, Biotechnol, Biochem., 70(2): 508-516 (2006).
[15] Tabrizian M., Mohammadpour K., Farazmand H., Cheraghi A. Synthesis and Field Evaluation of the Sex Pheromone of Stem Borer, Sesamia Cretica Lederer (Lep.: Noctuidae), plant protection (Scientific journal of agriculture), 40(3): 83-92 (2017).
[16] http://delloyd.50megs.com/MOBILE/drying.html
[17] Miyashita M., Yoshikoshi A., Griecol P. A., Pyridinium P-Toluenesulfonate. A Mild and Efficient Catalyst for the Tetrahydropyranylation of Alcohols, J. org. Chem., 42(23): 3772-3774 (1997).
[18] Chen H., Hu W., Ye X., Yongjun D., Method for Synthesizing Phyllocnistis Citrella Stainton Pheromone Compound , CN101712601 (2012).
[19] Ting L., Yang Y., Shuyang Zh., Synthesis Method of Chilosuppressalis (Walker) Pheromone Cis-11-Hexedecanal, CN104974027 (2015).
[20] Banasiak D. S. , Byers J. D., Process for Preparing Olefinic Aldehydes,  US4540826A (1985) .
[21] Paulo H. G., Zarbin L., Lorini M., Bianca G., Vidal D., Lima R., Sex Pheromone of Lonomia Obliqua: Daily Rhythm of Production, Identification, and Synthesis, J. Chem. Ecol., 33(3): 555-565 (2007).
[22] a) Ashby J., Styles J., Selection of an in Vitro Carcinogenicity Test for Derivatives of the Carcinogen Hexamethylphosphoramide, Brit. J. Cancer, 36(5): 564-571 (1977).
[22] b) Lee K. P., Trochimowicz H. J., Morphogenesis of Nasal Tumors in Rats Exposed to Hexamethylphosphoramide by Inhalation, Res., 68: 157–171 (1982).
 [23] Chi L., Pei C., Replacement of Carcinogenic Solvent HMPA By DMI in Insect sex Pheromone Synthesis, J. Chem. Ecol., 16: 3245-32553 (1990).