INSECTICIDAL ACTIVITY OF ALKYL DERIVATIVES 5-(P-AMINOPHENYL)-1,3,4-OXADIAZOL-2-THIONE
Abstract
Purpose: Study of the insecticidal activity of 1,3,4-oxadiazole derivatives against sap-sucking pests of garden crops (Aphis pomi) and ornamental plants (Macrosiphum rosae).
Methods and materials of the research: The material for the research was the alkyl derivatives of 5-(p-Аminophenyl)-1,3,4-oxadiazole-2-thione given in the text of the article. Adults of apple aphid (Aphis pomi) and rose aphid (Macrosiphum rosae). Research methods: primary screening for insecticidal activity was studied by incubating adult insect pests in Petri dishes. The insects were exposed to the substances for 24 hours.
Results: Sap-sucking pests – aphids cause significant harm to plants by spreading various viruses that greatly harm agricultural crops. To combat sap-sucking pests, chemical plant protection products with low toxicity to the environment are needed. According to the results of screening, it was proved that the biological effectiveness of substances 2-hexylthio-5-(p-Аminophenyl)-1,3,4-oxadiazole (1), 2-octylthio-5-(p-Аminophenyl)-1,3,4-oxadiazole (3) and 2-nonylthio-5-(p-Аminophenyl)-1,3,4-oxadiazole (4) was 98.0%, 97.0% and 99.5% in relation to M. rosae. Under the influence of 2-hexylthio-5-(p-Аminophenyl)-1,3,4-oxadiazole (1), 2-octylthio-5-(p-Аminophenyl)-1,3,4-oxadiazole (3) and 2-nonylthio-5-(p-Аminophenyl)-1,3,4-oxadiazole (4) at a dose of 5.0 mg/ml, the mortality of an individual A. pomi reached 99.0%, 83.0% and 90.0%, respectively.
The first studied lethal concentration (LC50) 2-hexylthio-5-(p-Аminophenyl)-1,3,4-oxadiazole (1), 2-heplthio-5-(p-Аminophenyl)-1,3,4-oxadiazole (2), 2-octylthio-5-(p-Аminophenyl)-1,3,4-oxadiazole (3), 2-nonylthio-5-(p-Аminophenyl)-1,3,4-oxadiazole (4) with contact action.
Conclusion: Thus, the creation of low toxicity insecticides that prevent the emergence of resistance based on alkyl derivatives of 5-(p-Аminophenyl)-1,3,4-oxadiazole-2-thione in plant protection may become topical directions.
The study showed that the substances 2-hexylthio-5-(p-Аminophenyl)-1,3,4-oxadiazole (1), 2-octylthio-5-(p-Аminophenyl)-1,3,4-oxadiazole (3) and 2-nonylthio-5-(p-Аminophenyl)-1,3,4 oxadiazole (4) at 0.5 mg/ml concentrations are highly toxic for M. rosae and A. pomi.
Research can be continued on the use of alkyl derivatives of 5-(p-Аminophenyl)-1,3,4-oxadiazole-2-thiones as agricultural remedies.
Downloads
References
Bleker P. M., Ament K, Dirgarde P. J, De bot M. T. J., Sхjurink R. K. Methods of scaring white flies. Patent Russia RU2484628C2, WO 2009/041814 (02.04.2009), p. 4.
Vasil’ev V.P., Livshits I.Z. Vrediteli plodovykh kul’tur [Pests of fruit crops]. M.: Kolos, 1984, p. 399.
Piper, Ross. Extraordinary Animals: An Encyclopedia of Curious and Unusual Animals. Greenwood Press, 2007, pp. 6-9.
Olga Popova Vitalievna [Insecticides: classification by species]. https://dezoff.ru/sredstva/insektitsidy/
Ismailova D.S. Sintez i khimicheskie prevrashcheniya proizvodnykh 5-(p-Aminofenil)-1,3,4-oksadiazol-2-tiona [Synthesis and chemical transformations of 5- (p-Aminophenyl) -1,3,4-oxadiazole-2-thione derivatives]. Tashkent, 2019, pp. 15-16.
Shetnev A.A., Presnukhina S.I. Sintez 5-gidroksi-4,5-digidro-1,2,4-oksadiazol-5-olov. Estestvoznanie: issledovaniya i obuchenie [Synthesis of 5-hydroxy-4,5-dihydro-1,2,4-oxadiazol-5-ols. Natural science: research and teaching]. Materialy konferentsii «Chteniya Ushinskogo» [Materials of the conference “Readings of Ushinsky”]. Yaroslavl, 2020, p. 299.
Qi Liu, Kai Chen, Qiang Wang, Jueping Ni, Yufeng Li, Hongjun Zhu,Yuan Ding. Synthesis, insecticidal activity, structure–activity relationship (SAR) and density functional theory (DFT) of novel anthranilicdiamides analogs containing 1,3,4-oxadiazole rings. RSC Adv., 2014, no. 4, pp. 55445-55451. https://doi.org/10.1039/C4RA06356B
Aziz-ur Rehman, Abbasi M.A., Siddiqui S.Z., et al. Synthesis of 2-{(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl}-N-substituted acetamides as potential antimicrobial and hemolytic agents. Pak. J. Pharm. Scien., 2016, vol. 29, no. 3, pp. 801–809.
Yasir A., Jahangir M., Aziz-ur-Rehman, Ishtiaq S., Shahid M. Antimicrobial, hemolytic and thrombolytic activities of some new N-substituted-2-({5- [(1E,3E) F-4-(1,3-benzodioxol-5-yl)-1,3-butadienyl]-1,3,4-oxadiazol-2-yl} sulfanyl) propanamides. Trop. J. Pharm. Res., 2017, vol. 16, iss. 8, pp. 1973–1981. https://doi.org/10.4314/tjpr.v16i8.30
Patel K.S., Raval K.N., Patel Sh. P., Patel A.G., Patel S.V. A review on synthesis and biological activities of pyrimidine derivatives. Inter. J. Pharm. Biol. Scien., 2012, vol. 2, pp. 170–182.
Myers M.C., Shah P.P., Diamond S.L., Huryna D.M., Smith A.B. Identification and synthesis of auniquethiocarbazate cathepsin L inhibitor. Bioorg. Med. Chem. Let., 2008, iss. 18, pp. 210–214. https://doi.org/10.1016/j.bmcl.2007.10.107
Shah H.P. Synthesis of novel 1,3,4-oxadiazole derivatives and their biological properties. Org. Chem. Indian J., 2012, iss. 8, pp. 367–369. https://www.tsijournals.com/articles/synthesis-of-novel-134oxadiazole-derivatives-and-their-biological-properties.pdf
Aziz-ur-Rehman, Fatima A., Abbasi M. A., Rasool Sh., Malik A., Ashraf M., Ahmad I., Ejaz S. A. Synthesis of new N-(5-chloro-2-methoxyphenyl)-4-(5-substituted-1,3,4-oxadiazol-2-ylthio) butanamide derivatives as suitable lipo–xygenase inhibitors. J. Saudi Chem. Soc., 2016, vol. 20, no. S1, pp. S488–S494. https://doi.org/10.1016/j.jscs.2013.02.006
Kotaiah Y., Harikrishna N., Nagaraj K., Venkata Rao C. Synthesis and antioxidant activity of 1,3,4-oxadiazole targed thieno [2,3-d] pyrimidine derivatives. J. Eur. Med. Chem., 2012, vol. 58, pp. 340–345. https://doi.org/10.1016/j.ejmech.2012.10.007
Akhtar T., Hameed Sh., Al-Masoudi N. A., Loddo R., Colla P. In vitro antitumor and antiviral activities of new benzothiazole and 1,3,4-oxadiazole-2-thione derivatives. Acta Pharm., 2008, no. 58, pp. 135–149. https://doi.org/10.2478/v10007-008-0007-2
Rajasekaran S., Gopalkrishna Rao, Abhiskek Chatterjee. Anti-Inflammatory and Anti-oxidant activity of some substituted Benzimidazole Derivatives. Inter. J. Drug Dev. Res., 2012, vol. 4, iss. 3, pp. 303–309.
Swarnkar D., Ameta R., Vyas R. Microwave-аssisted synthesis of some 1,3,4-oxadiazole derivatives and evaluation of their antibacterial and antifungal activity. Res. Article Org. Chem. Inter., 2014, Article ID 694060, pp. 1–6. https://doi.org/10.1155/2014/694060
Ismailova D.S., Ziyaev А.А., Elmuradov B. Z., Toshmurodov T.T., Bobakulov Kh.M., Zakirova R.P. Targeted synthesis and in vitro bactericidal and fungicidal activities of 2- alkylthio-5-(p-aminophenyl)-1,3,4-oxadiazoles. Journal of Basic and Applied Research, 2016, vol. 2, no 4, pp. 476-479. https://doi.org/10.1007/s13738-018-1530-9
Berestetskiy А.О., Grigoryeva E.N., Petrova М.О., Stepanycheva E.А. Insektitsidnye i fitotoksicheskie svoystva ekstraktov iz kul’tur nekotorykh patogenov zlakov [Insecticidal and phytotoxic properties of extracts from crops of some pathogens of cereals]. Mikologiya i fitopatologiya [Mikology and phytopathology], 2018, vol. 52, no. 6, pp. 408–419. https://doi.org/10.1134/S0026364818060016
Spisok pestitsidov i agrokhimikatov, razreshennykh dlya primeneniya v sel’skom khozyaystve respubliki Uzbekistan [List of pesticides and agrochemicals permitted for use in agriculture of the Republic of Uzbekistan]. Tashkent: Goskhimkomissiya, 2013, p. 26.
Puntener, W. Manual for Field Trials in Plant Production. 2nd Edition, Cibar-Geigy Limited Basele, 51, 1981, p. 205.
Finney D.J. Probit Analysis. 3rd Ed. London, Cambridge University Press, 1971.
Copyright (c) 2021 Saida M. Turayeva, Dilnoza S. Ismailova, Saida Kh. Muratova, Sitorabonu B. Allokulova
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
