Photodegradation study of the fenvalerate insecticide by 1H NMR, 13C NMR, and GC-MS and structural elucidation of its transformation products

Authors

  • Diène Diégane Thiaré Laboratoire de Photochimie et d’Analyse, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar; Unité de Chimie Environnementale et Interactions sur le Vivant, ULCO, Dunkerque, France
  • Pape Abdoulaye Diaw Laboratoire de Photochimie et d’Analyse, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar; Equipe Matériaux, Electrochimie et Photochimie Analytique, Université Alioune Diop, Bambey, Sénégal
  • Olivier Maurice Aly Mbaye Laboratoire de Photochimie et d’Analyse, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, BP 5005, Dakar
  • Diegane Sarr Laboratoire de Photochimie et d’Analyse, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, BP 5005, Dakar
  • Mame Diabou Gaye-Seye Laboratoire de Photochimie et d’Analyse, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, BP 5005, Dakar
  • Steven Ruellan Unité de Chimie Environnementale et Interactions sur le Vivant, ULCO, BP 59140 Dunkerque
  • Philippe Giamarchi Unité de Chimie Environnementale et Interactions sur le Vivant, ULCO, BP 59140 Dunkerque
  • François Delattre Unité de Chimie Environnementale et Interactions sur le Vivant, ULCO, BP 59140 Dunkerque
  • Atanasse Coly Laboratoire de Photochimie et d’Analyse, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, BP 5005, Dakar
  • Jean-Jacques Aaron Paris-Est Marne-la-Vallee University, Paris

DOI:

https://doi.org/10.20450/mjcce.2022.2571

Keywords:

fenvalerate, insecticide, 1H and 13C NMR, GC-MS analysis, Fenvalerate; insecticide; NMR; GC-MS; photodegradation; environment

Abstract

The photolysis of fenvalerate, a pyrethroid insecticide, was studied in acetonitrile by 1H nuclear magnetic resonance (NMR) and 13C NMR to identify the site of bond cleavage and gas chromatography-mass spectrometry (GC-MS) to establish the chemical structure of fenvalerate photoproducts. Ultraviolet (UV) irradiation of fenvalerate solutions was performed for 18 h with a solar light simulator, and the photolysis reaction obeyed first-order kinetics. Photolysis half-life time (t1/2) values ranged between 15.25 and 21.63 h (mean photodegradation percentage = 51.7 %) for 1H NMR and between 4.55 and 8.06 h (mean photodegradation percentage > 80 %) for 13C NMR. We observed five sites of bond cleavage, namely carbonyl-tertiary carbon, tertiary carbon-tertiary carbon, carbonyl-oxygen, carboxyl-tertiary carbon, and aromatic carbon-tertiary carbon, yielding photoproducts formation. GC-MS was associated with 1H NMR and 13C NMR to obtain a complete photodegradation mechanism. Before UV irradiation, two chromatogram peaks were obtained, due to the two fenvalerate isomers. Under irradiation, both peaks decreased, and new peaks appeared, corresponding to photoproduct formation. After a 12- to 13-h irradiation, 99.39 % of fenvalerate was degraded with a mean rate constant of 0.305 h–1. The chemical structure of the formed photoproducts was identified, either by using the National Institute of Standards and Technology (NIST) mass spectral database or by interpreting the mass spectra. Finally, a detailed mechanism was proposed for fenvalerate photodegradation.

Author Biography

Jean-Jacques Aaron, Paris-Est Marne-la-Vallee University, Paris

Laboratory Geomateriaux and Environment

Full Professor (Emeritus)

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Published

2022-12-30 — Updated on 2022-12-30

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How to Cite

Thiaré, D. D. ., Diaw, P. A. ., Mbaye, O. M. A. ., Sarr, D. ., Gaye-Seye, M. D. ., Ruellan, S. ., Giamarchi, P. ., Delattre, F. ., Coly, A. ., & Aaron, J.-J. (2022). Photodegradation study of the fenvalerate insecticide by 1H NMR, 13C NMR, and GC-MS and structural elucidation of its transformation products. Macedonian Journal of Chemistry and Chemical Engineering, 41(2), 193–208. https://doi.org/10.20450/mjcce.2022.2571

Issue

Vol. 41 No. 2 (2022)

Section

Photochemistry

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Copyright (c) 2022 Diène Diégane Thiaré, Pape Abdoulaye Diaw, Olivier Maurice Aly Mbaye, Diegane Sarr, Mame Diabou Gaye-Seye, Steven Ruellan, Philippe Giamarchi, François Delattre, Atanasse Coly, Jean-Jacques Aaron

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