Co-Authors:
Hapeman, C.J., Natural Resources Institute, Agricultural Research Service, U.S. Department of Agriculture, Beltsville, MD 20705, United States
Anderson, B.G., Environmental Engineering Program, Department of Civil Engineering, University of Maryland, College Park, MD 20742, United States
Torrents, A., Environmental Engineering Program, Department of Civil Engineering, University of Maryland, College Park, MD 20742, United States
Acher, A.J., Natural Resources Institute, Agricultural Research Service, U.S. Department of Agriculture, Beltsville, MD 20705, United States, Volcani Center, Institute of Soils and Water, Bet Dagan 50250, Israel
Abstract:
Bromacil ozonolysis was examined to determine the mechanism of product formation in an effort to optimize a chemical-microbial remediation strategy for contaminated waters. Two debrominated products, 3-sec-butyl-5-acetyl-5-hydroxyhydantoin (II) (24%) and 3-sec-butylparabanic acid (III) (56%), and a dibromohydrin, 3-sec-butyl-5,5-dibromo-6-methyl-6-hydroxyuracil (IV) (20%), were formed. The latter compound, arising from HOBr addition to bromacil, reverted back to starting material, causing the treated solution to remain somewhat phytotoxic. Mass balance studies provided evidence for parallel reaction pathways as opposed to a series pathway where II gives rise to III. Addition of hydrogen peroxide slightly decreased the rate of bromacil degradation while the addition of tert-butyl alcohol (t-BuOH), a hydroxy radical scavenger, increased the degradation rate, strongly suggesting that the mechanism does not involve hydroxy radicals but direct ozone attack at the double bond. A much lower yield of IV, 6%, relative to the control was observed with H2O2, whereas a slightly higher yield, 23%, was found with t-BuOH.
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