Oxidation of s-triazine pesticides
1994
Hapeman, C.J.
A study of the aqueous ozonation of 2-chloro-s-triazine pesticides, atrazine, simazine and propazine, is presented. The ozonation process gave rise to a mixture of products whose structure and abundance is dependent on the duration of ozonation. Structures were determined by chemical methods, HPLC, mass and NMR spectroscopy. In all the primary and secondary ozonation products oxidation of the N-alkyl to the N-acetyl and/or removal of the amino substituents occurred and the s-triazine ring remained intact. Dechlorination was not observed. Reaction of the amide was not found if an alkyl functionality was present. A proposed degradation pathway of the s-triazines is described as well as a reaction product profile of atrazine. The relative ozonation rate of N-ethyl was found to be five times greater than the rate of N-isopropyl as determined from competitive reactions and the rates of atrazine product formation.
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