Dechlorination of chloroacetanilide herbicides by thiosulfate salts
Dechlorination of chloroacetanilide herbicides by thiosulfate salts
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DOI：
10.1073/pnas.042105199
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发表时间：
2002-04-16
影响因子：
11.1
通讯作者：
Jury, WA
中科院分区：
文献类型：
--
作者：
Gan, JY;Wang, QQ;Jury, WA
卤代有机化合物(XOCs)是应用最广泛的合成化学品之一。许多XOCs对自然降解具有顽固性，已成为突出的环境污染物。一组这样的XOC是大量使用的氯乙酰苯胺除草剂。我们发现，在环境条件下，氯乙酰苯胺除草剂在水、沙子和土壤中能被硫代硫酸盐迅速脱氯。结构和动力学分析表明，该反应为S(N)2亲核取代反应，其中氯被硫代硫酸盐取代，除草剂解毒。实验室研究表明，该反应可用于去除水、土壤和沙子中的氯乙酰苯胺除草剂残留。我们的发现还表明，其他一些XOCs可能也会发生这种反应。由于常见的硫代硫酸盐是无害的产物(如化肥)，而且该反应选择性地在低水平的硫代硫酸盐中解毒XOCs，这一发现可能会导致一种从环境中安全去除某些XOCs的新方法。
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.