Hydrolysis of terbufos using simulated environmental conditions: rates, mechanisms, and product analysis.
This study focuses on the hydrolysis of terbufos, an organophosphorus pesticide. Combining GC-MS and wet chemistry methods, di-tert-butyl disulfide and formaldehyde were identified and quantified as major degradation products. Diethyl dithiophosphate was also indirectly identified as a degradation product under alkaline conditions. Hydrolysis rate constants of terbufos under homogeneous conditions were comparable to those of phorate and show relative insensitivity to pH under slightly acidic to neutral pH conditions, as the observed rate constants varied only in the range of (4.5-5.0) x 10(-6) s(-1) between pH 5.7 and 9.4; neutral hydrolysis is thus the most dominant hydrolysis pathway of terbufos in ambient waters. The mechanisms for terbufos hydrolysis and the formation of the major products and their temporal profiles are discussed. To assess the environmental impact of degradation products of this widely used pesticide, Microtox was used to analyze the toxicity of terbufos and two of its degradation products: diethyl dithiophosphate and di-tert-butyl disulfide; the EC(50) of terbufos was found to be >17 microM, whereas the EC(50) of di-tert-butyl disulfide was 1.3 microM.
Hong
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F
Department of Civil and Environmental Engineering, University of Cincinnati, Cincinnati, Ohio 45221-0071, USA.
Win
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KY
Pehkonen
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SO
D000818:Animals; D001681:Biological Assay; D002849:Chromatography, Gas; D003621:Daphnia / Q000187:drug effects; D004220:Disulfides / Q000032:analysis; D005557:Formaldehyde / Q000032:analysis; D008401:Gas Chromatography-Mass Spectrometry; D006868:Hydrolysis; D007306:Insecticides / Q000737:chemistry* / Q000633:toxicity; D007700:Kinetics; D017686:Oncorhynchus mykiss; D009946:Organothiophosphorus Compounds
D004220:Disulfides; D007306:Insecticides; D009946:Organothiophosphorus Compounds; D005557:Formaldehyde