Dechlorination of Chloroacetanilide Herbicides by Thiosulfate Salts
Halogenated organic compounds (XOCs) are among the most widely used synthetic chemicals. Many XOCs are recalcitrant to natural degradation and have become prominent environmental contaminants. One group of such XOCs are the heavily used chloroacetanilide herbicides. We have found that chloroacetanil...
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| Published in | Proceedings of the National Academy of Sciences - PNAS Vol. 99; no. 8; pp. 5189 - 5194 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
National Academy of Sciences
16.04.2002
National Acad Sciences |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0027-8424 1091-6490 1091-6490 |
| DOI | 10.1073/pnas.042105199 |
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| Abstract | Halogenated organic compounds (XOCs) are among the most widely used synthetic chemicals. Many XOCs are recalcitrant to natural degradation and have become prominent environmental contaminants. One group of such XOCs are the heavily used chloroacetanilide herbicides. We have found that chloroacetanilide herbicides are rapidly dechlorinated in water, sand, and soil by thiosulfate salts under ambient conditions. Structural and kinetics analysis suggests that the reaction occurred by SN2 nucleophilic substitution, in which the chlorine was replaced by thiosulfate and the herbicide was detoxified. Laboratory studies showed that this reaction could be used for removing residues of chloroacetanilide herbicides in water, soil, and sand. Our findings also suggest that some other XOCs may be subject to this reaction. Because common thiosulfate salts are innocuous products (e.g., fertilizers) and the reaction selectively detoxifies XOCs at low thiosulfate levels, this discovery may lead to a new way for safe removal of certain XOCs from the environment. |
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| AbstractList | Halogenated organic compounds (XOCs) are among the most widely used synthetic chemicals. Many XOCs are recalcitrant to natural degradation and have become prominent environmental contaminants. One group of such XOCs are the heavily used chloroacetanilide herbicides. We have found that chloroacetanilide herbicides are rapidly dechlorinated in water, sand, and soil by thiosulfate salts under ambient conditions. Structural and kinetics analysis suggests that the reaction occurred by S
N
2 nucleophilic substitution, in which the chlorine was replaced by thiosulfate and the herbicide was detoxified. Laboratory studies showed that this reaction could be used for removing residues of chloroacetanilide herbicides in water, soil, and sand. Our findings also suggest that some other XOCs may be subject to this reaction. Because common thiosulfate salts are innocuous products (e.g., fertilizers) and the reaction selectively detoxifies XOCs at low thiosulfate levels, this discovery may lead to a new way for safe removal of certain XOCs from the environment. Halogenated organic compounds (XOCs) are among the most widely used synthetic chemicals. Many XOCs are recalcitrant to natural degradation and have become prominent environmental contaminants. Halogenated organic compounds (XOCs) are among the most widely used synthetic chemicals. Many XOCs are recalcitrant to natural degradation and have become prominent environmental contaminants. One group of such XOCs are the heavily used chloroacetanilide herbicides. We have found that chloroacetanilide herbicides are rapidly dechlorinated in water, sand, and soil by thiosulfate salts under ambient conditions. Structural and kinetics analysis suggests that the reaction occurred by SN2 nucleophilic substitution, in which the chlorine was replaced by thiosulfate and the herbicide was detoxified. Laboratory studies showed that this reaction could be used for removing residues of chloroacetanilide herbicides in water, soil, and sand. Our findings also suggest that some other XOCs may be subject to this reaction. Because common thiosulfate salts are innocuous products (e.g., fertilizers) and the reaction selectively detoxifies XOCs at low thiosulfate levels, this discovery may lead to a new way for safe removal of certain XOCs from the environment. Halogenated organic compounds (XOCs) are among the most widely used synthetic chemicals. Many XOCs are recalcitrant to natural degradation and have become prominent environmental contaminants. One group of such XOCs are the heavily used chloroacetanilide herbicides. We have found that chloroacetanilide herbicides are rapidly dechlorinated in water, sand, and soil by thiosulfate salts under ambient conditions. Structural and kinetics analysis suggests that the reaction occurred by S(N)2 nucleophilic substitution, in which the chlorine was replaced by thiosulfate and the herbicide was detoxified. Laboratory studies showed that this reaction could be used for removing residues of chloroacetanilide herbicides in water, soil, and sand. Our findings also suggest that some other XOCs may be subject to this reaction. Because common thiosulfate salts are innocuous products (e.g., fertilizers) and the reaction selectively detoxifies XOCs at low thiosulfate levels, this discovery may lead to a new way for safe removal of certain XOCs from the environment. Halogenated organic compounds (XOCs) are among the most widely used synthetic chemicals. Many XOCs are recalcitrant to natural degradation and have become prominent environmental contaminants. One group of such XOCs are the heavily used chloroacetanilide herbicides. We have found that chloroacetanilide herbicides are rapidly dechlorinated in water, sand, and soil by thiosulfate salts under ambient conditions. Structural and kinetics analysis suggests that the reaction occurred by SN2 nucleophilic substitution, in which the chlorine was replaced by thiosulfate and the herbicide was detoxified. Laboratory studies showed that this reaction could be used for removing residues of chloroacetanilide herbicides in water, soil, and sand. Our findings also suggest that some other XOCs may be subject to this reaction. Because common thiosulfate salts are innocuous products (e.g., fertilizers) and the reaction selectively detoxifies XOCs at low thiosulfate levels, this discovery may lead to a new way for safe removal of certain XOCs from the environment. Halogenated organic compounds (XOCs) are among the most widely used synthetic chemicals. Many XOCs are recalcitrant to natural degradation and have become prominent environmental contaminants. One group of such XOCs are the heavily used chloroacetanilide herbicides. We have found that chloroacetanilide herbicides are rapidly dechlorinated in water, sand, and soil by thiosulfate salts under ambient conditions. Structural and kinetics analysis suggests that the reaction occurred by S(N)2 nucleophilic substitution, in which the chlorine was replaced by thiosulfate and the herbicide was detoxified. Laboratory studies showed that this reaction could be used for removing residues of chloroacetanilide herbicides in water, soil, and sand. Our findings also suggest that some other XOCs may be subject to this reaction. Because common thiosulfate salts are innocuous products (e.g., fertilizers) and the reaction selectively detoxifies XOCs at low thiosulfate levels, this discovery may lead to a new way for safe removal of certain XOCs from the environment.Halogenated organic compounds (XOCs) are among the most widely used synthetic chemicals. Many XOCs are recalcitrant to natural degradation and have become prominent environmental contaminants. One group of such XOCs are the heavily used chloroacetanilide herbicides. We have found that chloroacetanilide herbicides are rapidly dechlorinated in water, sand, and soil by thiosulfate salts under ambient conditions. Structural and kinetics analysis suggests that the reaction occurred by S(N)2 nucleophilic substitution, in which the chlorine was replaced by thiosulfate and the herbicide was detoxified. Laboratory studies showed that this reaction could be used for removing residues of chloroacetanilide herbicides in water, soil, and sand. Our findings also suggest that some other XOCs may be subject to this reaction. Because common thiosulfate salts are innocuous products (e.g., fertilizers) and the reaction selectively detoxifies XOCs at low thiosulfate levels, this discovery may lead to a new way for safe removal of certain XOCs from the environment. |
| Author | Koskinen, William C. Wang, Qiquan Gan, Jianying Yates, Scott R. Jury, William A. |
| AuthorAffiliation | Department of Environmental Sciences, University of California, Riverside, CA 92521; † Agricultural Research Service, U.S. Department of Agriculture, 450 West Big Springs Road, Riverside, CA 92507; and ‡ Agricultural Research Service, U.S. Department of Agriculture, 1991 Upper Buford Circle, Saint Paul, MN 55108 |
| AuthorAffiliation_xml | – name: Department of Environmental Sciences, University of California, Riverside, CA 92521; † Agricultural Research Service, U.S. Department of Agriculture, 450 West Big Springs Road, Riverside, CA 92507; and ‡ Agricultural Research Service, U.S. Department of Agriculture, 1991 Upper Buford Circle, Saint Paul, MN 55108 |
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| Cites_doi | 10.1021/es000973z 10.1002/etc.5620200504 10.1016/0165-1161(83)90010-9 10.1126/science.1063294 10.1104/pp.112.4.1595 10.1016/0041-008X(83)90231-4 10.1126/science.289.5488.2266 10.1021/es00029a011 10.2134/jeq1997.00472425002600020021x 10.1021/es00006a018 10.1073/pnas.82.21.7202 10.1038/35046063 10.1038/25470 10.1007/978-1-4684-7092-5_1 10.1016/S0065-230X(08)60848-9 10.1021/es9707318 10.1897/1552-8618(1992)11[473:AEOAGA]2.0.CO;2 10.1021/es950462q 10.2134/jeq2000.00472425002900050014x 10.1023/A:1007619919336 |
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| Notes | SourceType-Scholarly Journals-1 ObjectType-Feature-1 content type line 14 ObjectType-Article-1 ObjectType-Feature-2 content type line 23 Contributed by William A. Jury To whom reprint requests should be addressed at: Department of Environmental Sciences, 2208 Geology Building, University of California, Riverside, CA 92521-0424. E-mail: wajury@mail.ucr.edu. |
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| SubjectTerms | Acetamides Acetamides - chemistry Acetamides - pharmacology acetochlor alachlor Aquifers Biological Sciences Carbon chemical degradation Chemicals chemistry chlorides Chlorine Chlorine - chemistry Contaminants Dechlorination Environmental monitoring Gas Chromatography-Mass Spectrometry herbicide residues Herbicides Herbicides - chemistry Herbicides - pharmacology Kinetics metolachlor Models, Chemical Organic compounds pharmacology Physical Sciences Pollutants polluted soils pollution control propachlor Salts sand Soil pollution Soil salts Soil water Sustainable agriculture Temperature thiosulfates Thiosulfates - chemistry Time Factors |
| Title | Dechlorination of Chloroacetanilide Herbicides by Thiosulfate Salts |
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