Abstract
The method of synthesis of phosphonate derivatives of β-D-ribofuranoside was developed. Biological tests showed that prepared compounds possess high insecticidal activity and low toxicity.
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REFERENCES
Geldmacher-v.Mallinckrodt, M. and Machbert, G., in Analytical Toxicology for Clinical, Forensic and Pharmaceutical Chemists, Brandenberger, H. and Maes, R.A.A., Eds., Berlin: Walter de Gruyter, 1997, p. 215.
Rose, R.L., Hodgson, E., and Roe, R.M., in Toxicology, Marquardt, H., Schäfer, S.G., McClellan, R., and Welsch, F., Eds., San Diego: Academic Press, 1999, Ch. 28, p. 663.
Storm, J.E., in Patty’s Toxicology, Bingham, E. and Cohrssen, B., Eds., Hoboken: John Wiley & Sons, Inc., 2012, vol. 4, p. 1077. https://doi.org/10.1002/0471435139.tox095.pub2
Zinchenko, V.A., Khimicheskaya zashchita rastenii: sredstva, tekhnologiya i ekologicheskaya bezopasnost’ (Chemical Plant Protection: Products, Technology, qnd Environmental Safety), Moscow: KolosS, 2012, p. 102.
Pohanish, R., Sittig’s Handbook of Pesticides and Agricultural Chemicals, Norwich: William Andrew Publishing, 2014.
The Pesticide Manual, ed. J.A. Turner, Hampshire: BCPC (British Crop Production Council), 2018, 1408 p.
Fest, C., The Chemistry of Organophosphorus Pesticides, Berlin: Springer, 2013, 356 p.
Wilkinson, N., Organophosphorus Pesticides: Structural Characteristics, Mechanisms of Toxicity and Effects of Effects of Exposure on Health, New York: Nova Science Publishers Inc., 2016.
Eto, M., Organophosphorus Pesticides, Boca Raton: CRC Press, 2018.
Melnikov, N.N., Pestitsidy. Khimiya, tekhnologiya i primenenie (Pesticides. Chemistry, Technology, and Application), Moscow: Khimiya, 1987, p. 399.
Popov, S.Ya., Dorozhkina, L.A., and Kalinin, V.A., Osnovy khimicheskoi zashchity rastenii (Fundamentals of Chemical Plant Protection), Moscow: Art-Lion, 2003, p. 40.
Singh, B.K. and Walker, A., FEMS Microbiol. Rev., 2006, vol. 30. N 3, p. 428. https://doi.org/10.1111/j.1574-6976.2006.00018.x
Kushwaha, M., Verma, S., and Chatterjee, S., J. Environ. Quality, 2016, vol. 45. N 5, p. 1478. https://doi.org/10.2134/jeq2016.03.0100
Yadav, M., Shukla, A.K., Srivastva, N., Upadhyay, A.N., and Dubey, S.K., Critical Rev. Biotechnol., 2016, vol. 36, no. 4, p. 727. https://doi.org/10.3109/07388551.2015.1015958
Sengupta, S.K., Pandey, O.P., Singh, Y., and Yadav, K.S., Oriental J. Chem., 2008, vol. 24, no. 3, p. 1127.
Sun, D., Yang, C., Ming, W., Sun, L., Zhang, Q., and Chai, Y.J.,J. Pesticide Sci., 2011, vol. 36, no. 1, p. 44. https://doi.org/10.1584/jpestics.G10-60
Pandey, V.K., Chandra, R., Pandey, O.P., and Sengupta, S.K.,Pesticide Res. J., 2011, vol. 23, no. 1, p. 83.
Yang, C. and Sun, D., Asian J. Chem., 2012, vol. 24, no. 11, p. 5401.
Patil, B.L. and Kumar, P.L., Molecular Plant Pathology, 2015, vol. 16, no. 8, p. 775. https://doi.org/10.1111/mpp.12238
RU Patent 2570529, 2014; Byull. Izobret., no. 34, 2015.
RU Patent 2688819, 2018; Byull. Izobret., no. 15, 2019.
Belakhov, V.V. and Garabadzhiu, A.V., Russ. J. Gen. Chem., 2016, vol. 86, no. 13, p. 3002. https://doi.org/10.1134/S1070363216130120
Belakhov, V.V., Garabadzhiu, A.V., Boikova, I.V., and Novikova, I.I., Russ. J. Gen. Chem., 2017, vol. 87, no. 13, p. 3151. https://doi.org/10.1134/S1070363217130072
Belakhov, V.V., Garabadzhiu, A.V., Boikova, I.V., and Antonova, I.A., Russ. J. Gen. Chem., 2017, vol. 87, no. 3, p. 456. https://doi.org/10.1134/S1070363217031448
Mel’nikov, N.N., Novozhilov, K.V., and Belan, S.R., Pestitsidy i regulyatory rosta rastenii (Pesticides and plant growth regulators), Moscow: Khimiya, 1995, p. 323.
Elersek, T. and Filipic, M., in Pesticides – The Impacts of Pesticides Exposure, Stoytcheva, M., Ed., Rijeka: InTech, 2011, ch. 12, p. 243. https://doi.org/10.5772/14020
Tan, X.-S., Peng, H., and He, H.-W., Environmentally Friendly Alkylphosphonate Herbicides, Berlin: Springer, 2014.
Fridman, M., Belakhov, V., Lee, L.V., Liang, F.-S., Wong, C.-H., and Baasov, T., Angew. Chem. Int. Ed., 2005, vol. 44, no. 3, p. 447. https://doi.org/10.1002/anie.200462003
Nudelman, I., Rebbibo-Sabbah, A., Shallom-Shezifi, D., Hainrichson, M., Stahl, I., Ben-Yosef, T., and Baasov, T., Bioorg. Med. Chem. Lett., 2006, vol. 16, no. 24, p. 6310. https://doi.org/10.1016/j.bmcl.2006.09.013
Dess, D.B. and Martin, J.C., J. Org. Chem., 1983, vol. 48, no. 22, p. 4155. https://doi.org/10.1021/jo00170a070
Dess, D.B. and Martin, J.C., J. Am. Chem. Soc., 1991, vol. 113, no. 19, p. 7277. https://doi.org/10.1021/ja00019a027
Ireland, R.E. and Liu, L., J. Org. Chem., 1993, vol. 58, no. 10, p. 2899. https://doi.org/10.1021/jo00062a040
Abramov, V.S., Doklady Akad. Nauk SSSR, 1950, vol. 73, no. 4, p. 487.
Abramov, V.S., Zh. Obshch. Khim., 1952, vol. 22, no. 4, p. 647.
Abramov, V.S. and Semenova, N.A., Zh. Obshch. Khim., 1958, vol. 28, no. 11, p. 3056.
Bubb, W.A., Concepts in Magnetic Resonance (A), 2003, vol. 19, no. 1, p. 1. https://doi.org/10.1002/cmr.a.10080
Kandasamy, J., Atia-Glikin, D., Belakhov, V., and Baasov, T.,Med. Chem. Commun., 2011, vol. 2, no. 3, p. 165. https://doi.org/10.1039/c0md00195c
Fridman, M., Belakhov, V., Yaron, S., and Baasov, T., Org. Lett., 2003, vol. 5, no. 20, p. 3575. https://doi.org/10.1021/ol035213i
Hainrichson, M., Pokrovskaya, V., Shallom-Shezifi, D., Fridman, M., Belakhov, V., Shachar, D., Yaron, S., and Baasov, T., Bioorg. Med. Chem., 2005, vol. 13, no. 20, p. 5797. https://doi.org/10.1016/j.bmc.2005.05.058
Panarina, A.E., Dogadina, A.V., Zakharov, V.I., and Ionin, B.I.,Tetrahedron Lett., 2001, vol. 42, no. 26, p. 4365. https://doi.org/10.1016/S0040-4039(01)00711-0
Panarina, A.E., Aleksandrova, A.V., Dogadina, A.V., and Ionin, B.I., Russ. J. Gen. Chem., 2005, vol. 75, no. 1, p. 3. https://doi.org/10.1007/s11176-005-0162-9
Ionin, B.I., Ershov, B.A., and Kol’tsov, A.M., YaMR-spektroskopiya v organicheskoi khimii (NMR Spectroscopy In Organic Chemistry), Leningrad: Khimiya, 1983, p. 71.
Edmundson, R.S., in CRC Handbook of Phosphorus-31 Nuclear Magnetic Resonance Data, Tebby, J.C., Ed., Boca Raton: CRC Press, 1991, ch. 11, p. 297.
Glonek, T., Kopp, S.J., Kot, E., Pettegrew, J.W., Harrison, W.H., and Cohen, M.M., J. Neurochem., 1982, vol. 39, no. 5, p. 1210. https://doi.org/10.1111/j.1471-4159.1982.tb12557.x
Teleman, A., Richard, P., Toivari, M., and Penttila, M., Analyt. Biochem., 1999, vol. 272, no. 1, p. 71. https://doi.org/10.1006/abio.1999.4165
Quin, L.D. and Williams, A.J., Practical Interpretation of P-31 NMR Spectra and Computer Assisted Structure Verification, Toronto: Advanced Chemistry Development Inc., 2004, p. 29.
Fletcher, M.D., in Organophosphorus Reagents: A Practical Approach in Chemistry, Murphy, P.J., Ed., New York: Oxford University Press, 2008, p. 194.
Savignac, P. and Iorga, B., Modern Phosphonate Chemistry, Boca Raton: CRC Press-Taylor & Francis Group, 2013, p. 164.
Timperley, C., Best Synthetic Methods Organophosphorus(V) Chemistry, London: Elsevier Science & Technology, 2015, p. 237.
Cytlak, T., Skibi´nska, M., Kaczmarek, P., Kázmierczak, M., Rapp, M., Kubickia, M., and Koroniaka, H., RSC Adv., 2018, vol. 8, no. 22, p. 11957. https://doi.org/10.1039/c8ra01656a
Quin, L.D., A Guide to Organophosphorus Chemistry, New York: John Wiley & Sons, 2000, p. 367.
Corbridge, D.E.C., Phosphorus: Chemistry, Biochemistry and Technology, Boca Raton: CRC Press-Taylor & Francis Group, 2013, p. 1103.
Tajti, A. and Keglevich, G., in Organophosphorus Chemistry: Novel Developments, Keglevich, G., Ed., Berlin: De Gruyter, 2018, p. 53.
Zehnder, G., Gurr, G.M., Kuhne, S., Wade, M.R., Wratten, S.D., and Wyss, E., Ann. Rev. Entomol., 2007, vol. 52, p. 57. https://doi.org/10.1146/annurev.ento.52.110405.091337
Russo, D., Bosso, L., and Ancilloto, L., Agricult. Ecosyst. Environ., 2018, vol. 266, p. 31. https://doi.org/10.1016/j.agee.2018.07.024
Armarego, W.L.F. and Chai, C.L.L., Purification of Laboratory Chemicals, Oxford: Butterworth-Heinemann Press, 2012.
Ashmarin, I.P. and Vorobiev, A.A., Statisticheskie metody v mikrobiologicheskikh issledovaniyakh (Statistical Methods in Microbiological Research), Leningrad: Medgiz, 1962.
Belen’kii, M.L., Elementy kolichestvennoi otsenki farmakologicheskogo effekta (Elements of a Quantitative Assessment of the Pharmacological Effect), Leningrad: Medgiz, 1963.
European Convention for the Protection of Vertebrate Animals Used for Experimental and Other Scientific Purposes, European Treaty Series no. 123, 18.03.1986, Strasbourg (France): Council of Europe, 1986.
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Belakhov, V.V., Boikova, I.V. & Kolodyaznaya, V.A. Synthesis and Insecticidal Activity of 5-C-Phosphonate Derivatives of Aryl-1-thio-β-D-ribofuranoside. Russ J Gen Chem 90, 1845–1852 (2020). https://doi.org/10.1134/S1070363220100060
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DOI: https://doi.org/10.1134/S1070363220100060