By-products formation during degradation of isoproturon in aqueous solution. I: ozonation

Abstract

The degradation of the herbicide isoproturon during its ozonation in aqueous solution has been investigated with the aim of identifying intermediate as well as final by-products formed. At ambient temperature, phosphate-buffered (pH=7) isoproturon aqueous solutions (10, 10 −1 and 10 −3 mg/l) were ozonated in a semi-batch reactor, under a continuous flow of ozonated air whose ozone concentration was 9 and 0.9 mg O 3/l air for the highest and the two lower herbicide concentrations respectively. Measured steady-state ozone concentrations during the two sets of experiments (i.e. the highest and the lower isoproturon concentration) were 1.9 and 0.7 mg O 3/l. Under all of the above conditions, isoproturon was always completely removed in a period ranging between 5 and 15 min, essentially by reacting with molecular ozone. High-performance liquid chromatography-mass spectrometry (HPLC-MS) analyses indicate that primary degradation by-products are formed either by introducing OH groups in the aromatic ring and/or in the side-chain substituents, or by breaking down the isopropyl alkyl chain. The results also show that these primary intermediates are successively degraded yielding low molecular weight compounds such as aldehydes, simple organic acids and α-oxo-acids, which have been identified by gas chromatography-electron capture detection (GC-ECD), ion chromatography (IC) and GC-MS, respectively. On the basis of the analytical results, a pathway for the degradation of isoproturon by ozone has been proposed.