131068-72-9Relevant academic research and scientific papers
Structural elucidation of metolachlor photoproducts by liquid chromatography/high-resolution tandem mass spectrometry
Nicol, édith,Genty, Christophe,Bouchonnet, Stéphane,Bourcier, Sophie
, p. 2279 - 2286 (2015)
Rationale Metolachlor is one of the most intensively used chloroacetanilide herbicides in agriculture. It has been detected in water; consequently, under UV-visible irradiation, it can be transformed in degradation products (TPs). The structures of TPs were elucidated by liquid chromatography/high-resolution tandem mass spectrometry (LC/HR-MS/MS). The potential toxicities of these TPs were estimated by in silico tests. Methods Aqueous solutions of metolachlor were irradiated in a self-made reactor equipped with a mercury vapor lamp. Analyses were carried out using high-performance liquid chromatography coupled to quadrupole time-of-flight (QTOF) mass spectrometer. High-resolution m/z measurements, MS/MS and isotopic labeling experiments allowed structural elucidation of metolachlor TPs. Their toxicities were estimated in silico, using the T.E.S.T. program. Results Ten major metolachlor photoproducts were characterized by LC/MS/MS after irradiation of metolachlor in aqueous solution. Elucidation of their chemical structures was identified using high-resolution measurements and MS/MS experiments. They resulted from the combination of dehalogenation, hydroxylation and cyclisation processes. The potential oral rat lethal dose (LD50) was assessed with QSAR tests for metolachlor and each photoproduct. Results indicate that most of the TPs are much more toxic than metolachlor. Conclusions UV-vis irradiation of metolachlor in aqueous solution leads to the formation of ten photoproducts. QSAR estimations show that the location of added hydroxyl group(s) is of key relevance as regards to biological activity and that routine water analysis should take into account the TPs are more toxic than the parent molecule.
Photodegradation of Metolachlor in Water in the Presence of Soil Mineral and Organic Constituents
Mathew, Regi,Khan, Shahamat U.
, p. 3996 - 4000 (2007/10/03)
Photodegradation of metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)-acetamide] at 253.7 nm was carried out in water containing soil minerals (kaolinite, montmorillonite, and goethite) and fulvic acid under two different pH conditions. The rate of photolysis was dependent on the nature of the soil constituents and the initial pH of the medium. Based on the regression analysis, it was shown that the photodegradation followed the first-order kinetics with respect to the metolachlor concentration, and the half-life of the herbicide under UV irradiation was longer in the absence of soil constituents. Hydroxylation, dehalogenation, oxoquinoline formation, and demethylation were the main processes observed during the photolysis of metolachlor. More degradation products were formed in the presence of kaolinite, montmorillonite, and goethite than with fulvic acid and water alone. The major degradation product formed under UV irradiation in all the treatments was identified as 4-(2-ethyl-6-methylphenyl)-5-methyl-3-morpholine.
