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result sql = Dechlorination of chloroacetanilide herbicides by plant growth regulator sodium bisulfite.
Dechlorination of chloroacetanilide herbicides by plant growth regulator sodium bisulfite.
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char = ;code = 32
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char = f;code = 102
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char = e;code = 101
char = w;code = 119
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char = i;code = 105
char = l;code = 108
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char = ;code = 32
char = s;code = 115
char = i;code = 105
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char = ;code = 32
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char = d;code = 100
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char = d;code = 100
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char = s;code = 115
char = c;code = 99
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char = g;code = 103
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result sql = Chloroacetanilide herbicides are frequently detected in groundwater and surface waters, and pose high risks to aquatic biota. In this study, sodium bisulfite (NaHSO(3)), a plant growth regulator used in China, was used to remove three chloroacetanilide herbicides including alachlor, acetochlor and S-metolachlor. These herbicides were rapidly dechlorinated by NaHSO(3) in neutral conditions. The dechlorination was accelerated with increasing pH, temperature and NaHSO(3) concentrations. Kinetic analysis and mass spectrum identification revealed that the reaction followed S(N)2 nucleophilic substitution, in which the chlorine was replaced by the reactive specie sulfite. Alachlor and its isomer acetochlor had similar reaction rates, whereas they were more readily transformed than S-metolachlor that had larger steric hindrance and weaker electrophilicity. The transformation products were chloroacetanilide ethane sulfonic acids (ESAs), which were also encountered as major metabolites of these herbicides in natural environment via common metabolic pathways and were less toxic to green algae compared to the parent herbicides. These results indicate that NaHSO(3) can accelerate transformation of chloroacetanilide herbicides to the less toxic transformation products by nucleophilic substitution and dechlorination in aquatic environment. NaHSO(3) can be potentially used for the removal of chloroacetanilide herbicides from wastewater effluent, spill sites and accidental discharge.

Publication: Water Res. 2009 Aug ;43(14)::3566-74. :doi: 10.1016/j.watres.2009.05.002.
Publication Date: 2009 Aug
Study Author(s): Bian, Haitao;Chen, Jingwen;Cai, Xiyun;Liu, Ping;Wang, Ying;Huang, Liping;Qiao, Xianliang;Hao, Ce;
Institution: Key Laboratory of Industrial Ecology and Environmental Engineering, Department of Environmental Science and Technology, Dalian University of Technology, Linggong Road 2, Dalian 116024, PR China. [email protected]
Shortcut link to this study:
Chloroacetanilide herbicides are frequently detected in groundwater and surface waters, and pose high risks to aquatic biota. In this study, sodium bisulfite (NaHSO(3)), a plant growth regulator used in China, was used to remove three chloroacetanilide herbicides including alachlor, acetochlor and S-metolachlor. These herbicides were rapidly dechlorinated by NaHSO(3) in neutral conditions. The dechlorination was accelerated with increasing pH, temperature and NaHSO(3) concentrations. Kinetic analysis and mass spectrum identification revealed that the reaction followed S(N)2 nucleophilic substitution, in which the chlorine was replaced by the reactive specie sulfite. Alachlor and its isomer acetochlor had similar reaction rates, whereas they were more readily transformed than S-metolachlor that had larger steric hindrance and weaker electrophilicity. The transformation products were chloroacetanilide ethane sulfonic acids (ESAs), which were also encountered as major metabolites of these herbicides in natural environment via common metabolic pathways and were less toxic to green algae compared to the parent herbicides. These results indicate that NaHSO(3) can accelerate transformation of chloroacetanilide herbicides to the less toxic transformation products by nucleophilic substitution and dechlorination in aquatic environment. NaHSO(3) can be potentially used for the removal of chloroacetanilide herbicides from wastewater effluent, spill sites and accidental discharge.
PMID: 19520412

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