1996
DOI: 10.1021/es9503600
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Identification of a New Sulfonic Acid Metabolite of Metolachlor in Soil

Abstract: An ethanesulfonic acid metabolite of metolachlor (metolachlor ESA) was identified in soil-sample extracts by negative-ion, fast-atom bombardment mass spectrometry (FAB-MS) and FAB tandem mass spectrometry (FAB-MS/MS). Product-ion fragments from MS/MS analysis of the deprotonated molecular ion of metolachlor ESA in the soil extract can be reconciled with the structure of the synthesized standard. The elemental compositions of the (M -H)ions of the metolachlor ESA standard and the soil-sample extracts were confi… Show more

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Cited by 76 publications
(54 citation statements)
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“…LeBaron et al [27] reported that the carboxylic acid degradate of metolachlor, the oxidized version of the carbinol degradate, was the major degradation product of metolachlor in soil. In addition, Aga et al [28] identified an ethanesulfonic acid metabolite of metolachlor, which is formed via a glutathione conjugation pathway in soil. The increase in unknown polar degradates measured at 120 DAA possibly resulted from the formation of the carboxylic acid and sulfonic acid degradates, which were not identified with the methods of extraction and analysis utilized in the present study.…”
Section: Effect Of Soil Depthmentioning
confidence: 99%
“…LeBaron et al [27] reported that the carboxylic acid degradate of metolachlor, the oxidized version of the carbinol degradate, was the major degradation product of metolachlor in soil. In addition, Aga et al [28] identified an ethanesulfonic acid metabolite of metolachlor, which is formed via a glutathione conjugation pathway in soil. The increase in unknown polar degradates measured at 120 DAA possibly resulted from the formation of the carboxylic acid and sulfonic acid degradates, which were not identified with the methods of extraction and analysis utilized in the present study.…”
Section: Effect Of Soil Depthmentioning
confidence: 99%
“…Glutathione conjugation is the common detoxification method for metolachlor in plants (Cole, 1994;Field and Thurman, 1996) and for its microbial degradation pathway in soil unsaturated zones (Aga and Thurman, 2001;Aga et al, 1996;Aly and Schröder, 2008;Domagalski et al, 2008). In both plant and microbial degradation, glutathione-S-transferase mediates glutathione nucleophilic substitution at the chlorinated carbon of metolachlor.…”
Section: Introductionmentioning
confidence: 99%
“…Fifty percent dissipation times (DT 50 ) in field studies have ranged from 24 to 108 days (Frank et al 1991;Burgard et al 1993;Zheng and Cooper 1996;Aga et al, 1996) and carry over of significant metolachlor residues into the next cropping year has been observed in various soils (Braverman et al, 1986, Wood et al, 1987, Huang and Frink 1989, Sauer et al 1990Burgardetal., 1993). However, not much information is available on the persistence of metolachlor in tropical soil except a green house study conducted by Sahid and Wei (1993) under Malaysian conditions and no report is known to exist on field persistence of this herbicide.…”
Section: Introductionmentioning
confidence: 99%