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

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 identified 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 first-order kinetics. Degradation rates were faster under UV light (half-life of 51–59 min) compared to sunlight (half-life of 87–136 d). Under UV light, four major photoproducts were detected and tentatively identified 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 riboflavin, 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.