Hydrolysis and Photolysis of Herbicide Clomazone in Aqueous Solutions and Natural Water Under Abiotic Conditions

doi:10.1016/S2095-3119(13)60506-7

Journal of Integrative Agriculture ›› 2013, Vol. 12 ›› Issue (11): 2074-2082.DOI: 10.1016/S2095-3119(13)60506-7

Hydrolysis and Photolysis of Herbicide Clomazone in Aqueous Solutions and Natural Water Under Abiotic Conditions

CAO Jia, DIAO Xiao-ping , HU Ji-ye

1.School of Agriculture, Hainan University, Haikou 570228, P.R.China
2.School of Chemistry and Biological Engineering, University of Science and Technology Beijing, Beijing 100083, P.R.China

收稿日期:2013-01-10 出版日期:2013-11-01 发布日期:2013-12-08
通讯作者: Correspondence HU Ji-ye, Tel: +86-10-82376002, E-mail: jyhu@ustb.edu.cn; DIAO Xiao-ping, Tel: +86-898-66295028, E-mail: diaoxip@hainu.edu.cn
作者简介:CAO Jia, Tel: +86-898-66295028, E-mail: jiabiyang2006@126.com;
基金资助:
This study was sponsored by Shandong Cynda Chemical Co., Ltd. (Shandong, China) and the Project of Pesticide Registration Residue of Ministry of Agriculture of China (FRF-SD-12-010B).

Hydrolysis and Photolysis of Herbicide Clomazone in Aqueous Solutions and Natural Water Under Abiotic Conditions

CAO Jia, DIAO Xiao-ping , HU Ji-ye

1.School of Agriculture, Hainan University, Haikou 570228, P.R.China
2.School of Chemistry and Biological Engineering, University of Science and Technology Beijing, Beijing 100083, P.R.China

Received:2013-01-10 Online:2013-11-01 Published:2013-12-08
Contact: Correspondence HU Ji-ye, Tel: +86-10-82376002, E-mail: jyhu@ustb.edu.cn; DIAO Xiao-ping, Tel: +86-898-66295028, E-mail: diaoxip@hainu.edu.cn
About author:CAO Jia, Tel: +86-898-66295028, E-mail: jiabiyang2006@126.com;
Supported by:
This study was sponsored by Shandong Cynda Chemical Co., Ltd. (Shandong, China) and the Project of Pesticide Registration Residue of Ministry of Agriculture of China (FRF-SD-12-010B).

摘要/Abstract

摘要： The hydrolysis and photolysis of clomazone in aqueous solutions and natural water were assessed under natural and controlled conditions. Kinetics of hydrolysis and photolysis of clomazone were determined by HPLC-DAD. Photoproducts were identifi ed by HPLC-MS. No noticeable hydrolysis occurred in aqueous buffer solutions ((25±2)°C, pH (4.5±0.1), pH (7.4±0.1), pH (9.0±0.1); (50±2)°C, pH (4.5±0.1), pH (7.4±0.1)) or in natural water up to 90 d. At pH (9.0±0.1) and (50±2)°C the half-life of clomazone was 50.2 d. Clomazone photodecomposition rate in aqueous solutions under UV radiation and natural sunlight followed fi rst-order kinetics. Degradation rates were faster under UV light (half-life of 51-59 min) compared to sunlight (halflife of 87-136 d). Under UV light, four major photoproducts were detected and tentatively identifi ed according to HPLC-MS spectral information such as 2-chlorobenzamide, N-hydroxy-(2-benzyl)-2-methylpropan-amide, 2-[2-phenol]-4,4-dimethyl- 3-isoxazolidinone and 2-[(4,6-dihydroxyl-2-chlorine phenol)]-4,4-dimethyl-3-isoxazolidinone. These results suggested that clomazone photodegradation proceeds via several reaction pathways: 1) dehalogenation; 2) substitution of chlorine group by hydroxyl; 3) cleavage of the side chain. Photosensitizers, such as H2O2 and ribofl avin, could enhance photolysis of clomazone in natural sunlight. In summary, we found that photoreaction is an important dissipation pathway of clomazone in natural water systems.

关键词: clomazone , hydrolysis , photolysis , photoproducts , abiotic

Abstract: The hydrolysis and photolysis of clomazone in aqueous solutions and natural water were assessed under natural and controlled conditions. Kinetics of hydrolysis and photolysis of clomazone were determined by HPLC-DAD. Photoproducts were identifi ed by HPLC-MS. No noticeable hydrolysis occurred in aqueous buffer solutions ((25±2)°C, pH (4.5±0.1), pH (7.4±0.1), pH (9.0±0.1); (50±2)°C, pH (4.5±0.1), pH (7.4±0.1)) or in natural water up to 90 d. At pH (9.0±0.1) and (50±2)°C the half-life of clomazone was 50.2 d. Clomazone photodecomposition rate in aqueous solutions under UV radiation and natural sunlight followed fi rst-order kinetics. Degradation rates were faster under UV light (half-life of 51-59 min) compared to sunlight (halflife of 87-136 d). Under UV light, four major photoproducts were detected and tentatively identifi ed according to HPLC-MS spectral information such as 2-chlorobenzamide, N-hydroxy-(2-benzyl)-2-methylpropan-amide, 2-[2-phenol]-4,4-dimethyl- 3-isoxazolidinone and 2-[(4,6-dihydroxyl-2-chlorine phenol)]-4,4-dimethyl-3-isoxazolidinone. These results suggested that clomazone photodegradation proceeds via several reaction pathways: 1) dehalogenation; 2) substitution of chlorine group by hydroxyl; 3) cleavage of the side chain. Photosensitizers, such as H2O2 and ribofl avin, could enhance photolysis of clomazone in natural sunlight. In summary, we found that photoreaction is an important dissipation pathway of clomazone in natural water systems.

Key words: clomazone , hydrolysis , photolysis , photoproducts , abiotic

CAO Jia, DIAO Xiao-ping , HU Ji-ye. Hydrolysis and Photolysis of Herbicide Clomazone in Aqueous Solutions and Natural Water Under Abiotic Conditions[J]. Journal of Integrative Agriculture, 2013, 12(11): 2074-2082.

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Hydrolysis and Photolysis of Herbicide Clomazone in Aqueous Solutions and Natural Water Under Abiotic Conditions

Hydrolysis and Photolysis of Herbicide Clomazone in Aqueous Solutions and Natural Water Under Abiotic Conditions

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