title: Degradation mechanism of alachlor during direct ozonation and O(3)/H(2)O(2) advanced oxidation process.
abstract: The degradation of alachlor by direct ozonation and advanced oxidation process O(3)/H(2)O(2) was investigated in this study with focus on identification of degradation byproducts. The second-order reaction rate constant between ozone and alachlor was determined to be 2.5+/-0.1M(-1)s(-1) at pH 7.0 and 20 degrees C. Twelve and eight high-molecular-weight byproducts (with the benzene ring intact) from alachlor degradation were identified during direct ozonation and O(3)/H(2)O(2), respectively. The common degradation byproducts included N-(2,6-diethylphenyl)-methyleneamine, 8-ethyl-3,4-dihydro-quinoline, 8-ethyl-quinoline, 1-chloroacetyl-2-hydro-3-ketone-7-acetyl-indole, 2-chloro-2',6'-diacetyl-N-(methoxymethyl)acetanilide, 2-chloro-2'-acetyl-6'-ethyl-N-(methoxymethyl)-acetanilide, and two hydroxylated alachlor isomers. In direct ozonation, four more byproducts were also identified including 1-chloroacetyl-2,3-dihydro-7-ethyl-indole, 2-chloro-2',6'-ethyl-acetanilide, 2-chloro-2',6'-acetyl-acetanilide and 2-chloro-2'-ethyl-6'-acetyl-N-(methoxymethyl)-acetanilide. Degradation of alachlor by O(3) and O(3)/H(2)O(2) also led to the formation of low-molecular-weight byproducts including formic, acetic, propionic, monochloroacetic and oxalic acids as well as chloride ion (only detected in O(3)/H(2)O(2)). Nitrite and nitrate formation was negligible. Alachlor degradation occurred via oxidation of the arylethyl group, N-dealkylation, cyclization and cleavage of benzene ring. After O(3) or O(3)/H(2)O(2) treatment, the toxicity of alachlor solution examined by the Daphnia magna bioassay was slightly reduced.
authors.affiliation: Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing, China. qiangz@rcees.ac.cn
authors.forename: Zhimin
authors.initials: Z
authors.lastname: Qiang
authors.forename: Chao
authors.initials: C
authors.lastname: Liu
authors.forename: Bingzhi
authors.initials: B
authors.lastname: Dong
authors.forename: Yalei
authors.initials: Y
authors.lastname: Zhang
mesh_terms: D000081:Acetamides / Q000737:chemistry / Q000378:metabolism*; D052918:Environmental Restoration and Remediation; D006540:Herbicides / Q000737:chemistry / Q000378:metabolism*; D006861:Hydrogen Peroxide / Q000737:chemistry*; D007700:Kinetics; D010084:Oxidation-Reduction; D010126:Ozone / Q000737:chemistry*
chemical_list: D000081:Acetamides; D006540:Herbicides; C000188:alachlor; D010126:Ozone; D006861:Hydrogen Peroxide