Degradation of Chlorotriazine Pesticides by Sulfate Radicals and the Influence of Organic Matter

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University of Duisburg-Essen, Instrumental Analytical Chemistry, Universitätsstr. 5, D-45141 Essen, Germany
IWW Water Centre, Moritzstr. 26, D-45476 Mülheim an der Ruhr, Germany
§ Max-Planck-Institut für chemische Energiekonversion, Stiftstrasse 34-36, P.O. Box 101365, D-45470 Mülheim an der Ruhr, Germany
Centre for Water and Environmental Research, Universitätsstraße 2, D-45117 Essen, Germany
Cite this: Environ. Sci. Technol. 2015, 49, 3, 1673–1680
Publication Date (Web):October 27, 2014
https://doi.org/10.1021/es503496u
Copyright © 2014 American Chemical Society
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Abstract

Atrazine, propazine, and terbuthylazine are chlorotriazine herbicides that have been frequently used in agriculture and thus are potential drinking water contaminants. Hydroxyl radicals produced by advanced oxidation processes can degrade these persistent compounds. These herbicides are also very reactive with sulfate radicals (2.2–3.5 × 109 M–1 s–1). However, the dealkylated products of chlorotriazine pesticides are less reactive toward sulfate radicals (e.g., desethyl-desisopropyl-atrazine (DEDIA; 1.5 × 108 M–1 s–1)). The high reactivity of the herbicides is largely due to the ethyl or isopropyl group. For example, desisopropyl-atrazine (DIA) reacts quickly (k = 2 × 109 M–1 s–1), whereas desethyl-atrazine (DEA) reacts more slowly (k = 9.6 × 108 M–1 s–1). The tert-butyl group does not have a strong effect on reaction rate, as shown by the similar second order reaction rates between desethyl-terbuthylazine (DET; k = 3.6 × 108 M–1 s–1) and DEDIA. Sulfate radicals degrade a significant proportion of atrazine (63%) via dealkylation, in which deethylation significantly dominates over deisopropylation (10:1). Sulfate and hydroxyl radicals react at an equally fast rate with atrazine (k (hydroxyl radical + atrazine) = 3 × 109 M–1 s–1). However, sulfate and hydroxyl radicals differ considerably in their reaction rates with humic acids (k (sulfate radical + humic acids) = 6.8 × 103 L mgC–1 s–1 (mgC = mg carbon); k (hydroxyl radical + humic acids) = 1.4 × 104 L mgC–1 s–1). Thus, in the presence of humic acids, atrazine is degraded more efficiently by sulfate radicals than by hydroxyl radicals.

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Competition kinetics, calculation of fractions reacting with an oxidant, radiation source, use of buffers in the presence of humic acids, determination of SO4•– and OH rate constants with dissolved organic matter, determination of response factors of atra-imine in HPLC-DAD measurements, and additional figures. This material is available free of charge via the Internet at http://pubs.acs.org.

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