Issue 3, 2011
From the journal:

New Journal of Chemistry

Reaction kinetics and mechanisms of neonicotinoidpesticides with sulfate radicals†

María L. Dell'Arciprete,a   Carlos J. Cobos,a   Daniel O. Mártire,a   Jorge P. Furlongb  and  Mónica C. Gonzalez*a  

* Corresponding authors

a Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas (INIFTA), Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Casilla de Correo 16, Sucursal 4, (1900) La Plata, Argentina
E-mail: gonzalez@inifta.unlp.edu.ar

b LADECOR, Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Casilla de Correo 16, Sucursal, (1900) La Plata, Argentina

Abstract

The reaction kinetics and mechanisms of three neonicotinoid insecticides, imidacloprid (IMD), thiacloprid (THIA) and acetamiprid (ACT) with sulfate radicals were studied by flash-photolysis of peroxodisulfate, S2O82−. The absolute rate constants (3 ± 1) × 108, (1.1 ± 0.6) × 109, and (3 ± 1) × 109 M−1 s−1 were determined for IMD, ACT, and THIA, respectively. The reactivity and absorption spectra of the observed organic intermediates are in line with those reported for α-aminoalkyl radicals, and their absorption spectra agree very well with those estimated employing the time-dependent density functional theory with explicit account for bulk solvent effects. The mono- and di-hydroxylated oxidation products of the insecticides were identified as primary degradation products. The proposed reaction mechanism supports an initial charge transfer from the amidine nitrogen of the insecticides to the sulfate radicals. The pyridine moiety of the insecticides remains unaffected even after long irradiation times, until nicotinic acid is formed.

Graphical abstract: Reaction kinetics and mechanisms of neonicotinoid pesticides with sulfate radicals

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Article information

DOI
https://doi.org/10.1039/C0NJ00726A
Article type
Paper
Submitted
22 Sep 2010
Accepted
22 Nov 2010
First published
22 Dec 2010

New J. Chem., 2011,35, 672-680

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Reaction kinetics and mechanisms of neonicotinoid pesticides with sulfate radicals

M. L. Dell'Arciprete, C. J. Cobos, D. O. Mártire, J. P. Furlong and M. C. Gonzalez, New J. Chem., 2011, 35, 672 DOI: 10.1039/C0NJ00726A

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