Synthesis of a synthetic analogue for the Sitophilus weevil aggregation pheromone and study on its hygienic and toxicological indexes

Gulnara SHAKIRZYANOVA, Liliya ROMANOVA, Bahrom BABAEV, Vladimir АBDUKACHAROV, Tulkun ISKANDAROV, Sabina GAYIBOVA

Abstract


The work was initiated to study hygienic and toxicological indices of a synthetic analogue for the Sitophilus weevil aggregation pheromone. The toxicity testing of 5-hydroxy-4-methyl-3-heptanone demonstrated its extremely low toxicity for the warm-blood animals, as compared to the one of the typical pesticides. The average lethal dose of the product per orally administered to the white mice was established to be 4375.0 mg kg-1 LD16 and LD84 being 2225.0 mg kg-1 and 6550.0 mg kg-1, respectively. The average lethal dose for rabbits was 5900.0 mg kg-1 5-hydroxy-4-methyl-3-heptanone proved to have a mild skin and conjunctival irritant action, and equally mild functional cumulation. As to chronic toxicity, the acceptable daily dose of 4.3 mg/person/d was calculated and scientifically substantiated. The odor threshold was determined at the dose ranging from 0.35 to 0.7 mg l-1 with the practical limit ranging from 0.35 to 1.5 mg l-1, taste sensation threshold was found at the dose ranging from 1.0 to 3.0 mg l-1 with the practical limit ranging from 3.0 to 7.0 mg l-1

Keywords


L-proline; aggregation pheromone; sitophilure; aldol condensation; pest insect, toxicological indexes

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References


Abasov, M., Atanov, M., Kuzina, N., Kuzina, A., & Ponomarev, V. (2015). Program for the identification of quarantine pests in the Russian Federation using pheromone and color traps in areas of greatest pest risk for 2016-2018 (In Russian). https://vniikr.ru/files/contact/pr_16_18.pdf

Adda, C., Borgemeister, C., Biliwa, A., Meikle, W., Markham, R., & Poehling, H. (2002). Integrated pest management in post-harvest maize: A case study from the Republic of Togo (West Africa). Agriculture, Ecosystems & Environment, 93(1-3), 305-321. https://doi.org/10.1016/s0167-8809(01)00344-9

Ambrogi, B. G., & Zarbin, P. H. (2008). Aggregation pheromone in Sternechus subsignatus (Coleoptera: Curculionidae): olfactory behaviour and temporal pattern of emission. Journal of Applied Entomology, 132(1), 54-58. https://doi.org/10.1111/j.1439-0418.2007.01240.x

Ambrogi, B. G., Vidal, D. M., Zarbin, P. H., & Rosado-Neto, G. H. (2009). Aggregation pheromone in Curculionidae (Insecta: Coleoptera) and their taxonomic implication. Quimica Nova, 32(8), 2151-2158. http://dx.doi.org/10.1590/S0100-40422009000800029

Athanassiou, C.G. & Bucheloc, G.Th. (2001). The presence of Sitophilus zeamais Motschulsky (Coleoptera: Curculionidae) in Greece: distribution and food preferences. Annales of Benaki Phytopathological Institute, 19, 140–144.

Bohinc, T., Horvat, A., Ocvirk, M., Košir, I. J., Rutnik, K., & Trdan, S. (2020a). The first evidence of the Insecticidal potential of plant powders from invasive alien plants against rice weevil under laboratory conditions. Applied Sciences, 10(21), 7828. https://doi.org/10.3390/app10217828

Bohinc, T., Horvat, A., Andrić, G., Golić, M. P., Kljajić, P., & Trdan, S. (2020b). Natural versus synthetic zeolites for controlling the maize weevil (Sitophilus zeamais)–like Messi versus Ronaldo? Journal of Stored Products Research, 88, 101639. https://doi.org/10.1016/j.jspr.2020.101639

Deichmann, W.B., LeBlanc, T.J. (1943) Determination of the approximate lethal dose with approximately six animals. The Journal of Industrial Hygiene and Toxicology, 25, 415–417.

Demyanovich, V., Shishkina, I., & Zefirov, N. (2001). Catalyzed asymmetric dialkylzinc addition to benzaldehyde in the presence of new chiral ligands δ-(1-phenethyl) aminoalcohols. Chirality, 13(8), 507-509. https://doi.org/10.1002/chir.1068

Denmark, S. E., Stavenger, R. A., & Wong, K. T. (1998). A notable exception is Denmark’s chiral Lewis base-catalyzed Mukayama-type aldol reaction. Journal of Organic Chemistry, 63(4), 918-919. https://doi.org/10.1021/jo972168h

Faustini, D. L., Giese, W. L., Phillips, J. K., & Burkholder, W. E. (1984). Aggregation pheromone of the male granary weevil, Sitophilus granarius (L.). Journal of Chemical Ecology, 8(4), 679-687. https://doi.org/10.1007/bf00988309

Fauve, A., & Veschambre, H. (1984). Use of biological systems for the preparation of chiral molecules IV: A two-step chemoenzymatic synthesis of a natural pheromone (4r, 5s)-(−)-4-methyl 5-hydroxy heptan 3-one, sitophilure. Tetrahedron Letters, 28(42), 5037-5040. https://doi.org/10.1016/s0040-4039(00)96689-9

Hayashi, Y. (2005). Recent progress in the asymmetric organocatalysis. ChemInform, 36(41), 464-477. https://doi.org/10.1002/chin.200541296

Iskandarov, T., Iskandarova, G., & Romanova, L. (2015, September 22). Sanitary and preventive instruction of the Republic of Uzbekistan № 0321-15. Hygienic classification of pesticides by toxicity and hazard. Ministry of Health of the Republic of Uzbekistan. https://www.minzdrav.uz/pdf/read.php?f=48050

Ismuxambetov, J. D. (2015). Stock pest control in Kazakhstan. Bulletin of Science of the Kazakh Agrotechnical University named after S. Seifullin (interdisciplinary), 2(85), 4-12.

List, B., Lerner, R. A., & Barbas III, C. F. (2010). Proline-catalyzed direct asymmetric aldol reactions. Journal of the American Chemical Society, 31(22), 2395-2396. https://doi.org/10.1002/chin.200022046

Oehlschlager, A. C. (2016). Palm weevil pheromones – discovery and use. Journal of Chemical Ecology, 42(7), 617-630. https://doi.org/10.1007/s10886-016-0720-0

Orlov V. N. (2006). Insect-pests of grain-crops. Moscow: Printing City, 102 p.

Petrunja, E. V. (2011). Grain stock pest control measures: classic and new (in Russian). Pest Management, 2(78), 20-23.

Phillips, J. K., Walgenbach, C. A., Klein, J. A., Burkholder, W. E., Schmuff, N. R., & Fales, H. M. (1985). (R*, S*)-5-hydroxy-4-methyl-3-heptanone male-produced aggregation pheromone of Sitophilus oryzae (L.) and S. zeamais Motsch. Journal of Chemical Ecology, 11(9), 1263-1274. https://doi.org/10.1007/bf01024114

Ramachandran, P., Xu, W., & Brown, H. C. (1996). Contrasting steric effects of the ketones and aldehydes in the reactions of the diisopinocampheyl enolborinates of methyl ketones with aldehydes. Tetrahedron Letters, 37(28), 4911-4914. https://doi.org/10.1016/0040-4039(96)00969-0

Shakirzyanova, G. S., Babaev, B. N., Elmuradov, B. G., Mamadrahimov, A., & Abdukacharov, V. S. (2018). Synthesis of optical active isomer – sitophilure – aggregetion pheromone of rice (Sitophilus oryzae L.), grainary (S. granarius L.) and maize. Bulletin of Science and Education, Moscow, 9(33), 15-21.

Smith, III, A. B., & Levenberg, P. A. (1981). Oxidation of β-hydroxyketones and esters: A convenient synthesis of 1, 3-Diketones and β-ketoesters. Synthesis, (07, 567-570. https://doi.org/10.1055/s-1981-29532

Sousa, A., Faroni, L., Pimentel, M., & Guedes, R. (2009). Developmental and population growth rates of phosphine-resistant and -susceptible populations of stored-product insect pests. Journal of Stored Products Research, 45(4), 241-246. https://doi.org/10.1016/j.jspr.2009.04.003

Trdan, S., Čuk, J., Poženel, A., Bavcon Kralj, M., Rot, M., Carlevaris, B., Žežlina, I., Vidrih, M., Laznik, Ž., & Bohinc, T. (2018). Field testing of different synthetic attractants for mass trapping of common European cockchafer (Melolontha melolontha [L.], Coleoptera, Scarabaeidae) adults. Acta Agriculturae Scandinavica, Section B — Soil & Plant Science, 69(2), 174-180. https://doi.org/10.1080/09064710.2018.1524020

Ukeh, D. A., & Udo, I. A. (2008). Analysis of insect populations in stored crops in Cross River state, Nigeria. Global Journal of Pure and Applied Sciences, 14(1), 31-36. https://doi.org/10.4314/gjpas.v14i1.16769

Ukeh, D. A., Umoetok, S. B., Bowman, A. S., Jennifer Mordue (Luntz), A., Pickett, J. A., & Birkett, M. A. (2012). Alligator pepper, Aframomum melegueta, and ginger, Zingiber officinale, reduce stored maize infestation by the maize weevil, Sitophilus zeamais in traditional African granaries. Crop Protection, 32, 99-103. https://doi.org/10.1016/j.cropro.2011.10.013

Unelius, C. R., Park, K., McNeill, M., Wee, S. L., Bohman, B., & Suckling, D. M. (2012). Identification and electrophysiological studies of (4s, 5s)-5-hydroxy-4-methyl-3-heptanone and 4-methyl-3, 5-heptanedione in male Lucerne weevils. Naturwissenschaften, 100(2), 135-143. https://doi.org/10.1007/s00114-012-1003-4

Zakladnoi, G. A., Sokolov, E. A., Kogteva, E. F., & Chirkov, A. M. (2003). A guide to pests of grain stocks and “Expanse” as a means of combating them. Moscow: Publishing House of Moscow State Educational Institution, 107 р.




DOI: http://dx.doi.org/10.14720/aas.2021.117.2.1961

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