Abstract
Electrochemical transformation of difenoconazole (3-chloro-4-((2RS,4RS;2RS,4SR)-4-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-2-yl)phenyl 4-chlorophenyl ether) is studied in mixed-aqueous solvents (a mixture of aqueous ammonium formate (pH = 7.4) and acetonitrile (ACN) in a volume ratio of 3 : 1); the difenoconazole solution’s concentration is 100 μg/mL. The products are analyzed by chromatography–mass spectroscopy (HPLC/ESI MS/MS). Many of the products of difenoconazole electrochemical transformations result from oxidation involving the aliphatic part of the molecule.
Similar content being viewed by others
REFERENCES
Gil, Y. and Sinfort, C., Atmos. Environ., 2005, vol. 39, p. 5183.
Akiyama, Y., Yoshioka, N., and Tsuji, M., J. Food Hyg. Soc. Jpn., 1998, vol. 39, p. 303.
Andreu, V. and Pico, Y., TrAC, Trends Anal. Chem., 2004, vol. 23, p. 772.
Rashidi, M.Al., Atmos. Environ., 2011, vol. 45, p. 5997.
Pesticidy. http://www.pesticidy.ru/active_substance/ difenoconazole. Accessed July 16, 2018.
Zenkevich, I.G. and Pushkareva, T.I., J. Anal. Chem., 2017, vol. 72, no. 10, p. 1061.
Zenkevich, I.G. and Pushkareva, T.I., Russ. J. Gen. Chem., 2018, vol. 88, no. 1, p. 7.
Urzúa, J., González-Vargas, C., Sepúlveda, F., Ureta-Zañartu, M.S., and Salazar, R., Chemosphere, 2013, vol. 93, p. 2774.
Hana, W., Zhonga, C., Liang, L., and Suna, Y., Electrochim. Acta, 2014, vol. 130, p. 179.
Patel, D. and Kaulgaud, P., Indian Patent 249242, 2011. http://www.allindianpatents.com/patents/249242-process-for-preparing-triazole-compounds. Accessed July 16, 2018.
Reet, G.V., Heeres, J., and Wals, L., US Patent 4079062, 1978.
Hu, A., Chen, X., Tang, J., Ye, J., and Zhang, M., CN Patent 102432566, 2005.
Green, R.A., Brown, R.C.D., and Pletcher, D., J. Flow Chem., 2015, vol. 5, no. 1, p. 31.
Steckhan, E., Chemosphere, 2001, vol. 43, p. 63.
Paddon, C.A., J. Appl. Electrochem., 2006, vol. 41, no. 61, p. 617.
Pélisson, C.-H., Denicourt-Nowicki, A., Meriadec, C., Greneche, J.-M., and Roucoux, A., Magnetically recoverable palladium (0) nanocomposite catalyst for hydrogenation reactions in water, ChemCatChem, 2015, vol. 7, p. 309.
Zenkevich, I.G., Moeder, M., Koeller, G., and Scharder, S., J. Chromatogr. A, 2004, vol. 1025, p. 227.
Mehta, S., Phase I metabolism—Oxidative reactions—Oxidation of aliphatic and alicyclic compounds. https://pharmaxchange.info/2014/09/phase-i-metabolism-oxidative-reactionsoxidation-of-aliphatic-and-alicyclic-compounds. Accessed July 16, 2018.
Ferrando-Climent, L., Collado, N., Buttiglieri, G., Gros, M., Rodriguez-Roda, I., Rodriguez-Mozaz, S., and Barceló, D., Sci. Total Environ., 2012, vol. 438, p. 404.
Pushkareva, T.I. and Zenkevich, I.G., Vestn. S.-Peterb. Univ., Ser. 4: Fiz., Khim., 2017, no. 1, p. 57.
Mehta, S., Phase I metabolism—Oxidative reactions—Oxidation of aromatic compounds. https://pharmaxchange.info/2014/02/phase-i-metabolism-oxidative-reactionsoxidation-of-aromatic-compounds. Accessed July 16, 2018.
ACKNOWLEDGMENTS
We are grateful to the administration of the Federal Medical Biological Agency “Occupational Pathology and Human Ecology” for using their analytical facilities and to Cand. Sci. (Chem.) O.K. Ostroukhova, an analytical chemist at the Federal State Budget Scientific Institute “All-Russian Institute of Plant Protection” for providing us with a sample of difenoconazole.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated by A. Kukharuk
About this article
Cite this article
Pushkareva, T.I., Zenkevich, I.G. Electrochemical Oxidation of Difenoconazole in Solutions: LC/MS Identification of Reaction Products. Moscow Univ. Chem. Bull. 74, 127–133 (2019). https://doi.org/10.3103/S0027131419030106
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.3103/S0027131419030106