Carbon and nitrogen stable isotope fractionation during abiotic hydrolysis of pesticides

Chemosphere
Jeremy MasbouGwenaël Imfeld

Abstract

Compound-specific Stable Isotope Analysis (CSIA) has been recently established as a tool to study pesticide degradation in the environment. Among degradative processes, hydrolysis is environmentally relevant as it can be chemically or enzymatically mediated. Here, CSIA was used to examine stable carbon and nitrogen isotope fractionation during abiotic hydrolysis of legacy or currently used pesticides (chloroacetanilide herbicides: Acetochlor, Alachlor, S-Metolachlor and Butachlor, acylalanine fungicide: Metalaxyl, and triazine herbicide: Atrazine). Degradation products analysis and CN dual-CSIA allowed to infer hydrolytic degradation pathways from carbon and nitrogen isotopic fractionation. Carbon isotopic fractionation for alkaline hydrolysis revealed similar apparent kinetic isotope effects (AKIEC = 1.03-1.07) for the 6 pesticides, which were consistent with SN2 type nucleophilic substitutions. Neither enantio-selectivity (EF ≈ 0.5) nor enantio-specific isotope fractionation occurred during hydrolysis of R (AKIEC = 1.04 ± 0.01) and S (AKIEC = 1.04 ± 0.02) enantiomers of a racemic mixture of Metalaxyl. Dual element isotope plots enabled to tease apart CCl bond breaking of alkane (Λ ≈ εN/εC ≈ 0, Acetochlor, Butachlor) and aroma...Continue Reading

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Citations

Sep 17, 2019·Water Environment Research : a Research Publication of the Water Environment Federation·B S Choudri, Yassine Charabi
Dec 19, 2020·Chemosphere·Patrick Höhener, Gwenaël Imfeld
Aug 8, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Eun-Ji WonKyung-Hoon Shin
Oct 19, 2019·Analytical Chemistry·Violaine PonsinDaniel Hunkeler
Dec 19, 2021·Environmental Science & Technology·Monica E McFaddenDavid M Cwiertny

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