Hydrolysis and Photolysis Kinetics, and Identification of Degradation Products of the Novel Bactericide 2-(4-Fluorobenzyl)-5-(Methylsulfonyl)-1,3,4-Oxadiazole in Water

Int J Environ Res Public Health. 2018 Dec 5;15(12):2741. doi: 10.3390/ijerph15122741.

Abstract

Hydrolysis and photolysis kinetics of Fubianezuofeng (FBEZF) in water were investigated in detail. The hydrolysis half-lives of FBEZF depending on pH, initial concentration, and temperature were (14.44 d at pH = 5; 1.60 d at pH = 7), (36.48 h at 1.0 mg L-1; 38.51 h at 5.0 mg L-1; and 31.51 h at 10.0 mg L-1), and (77.02 h at 15 °C; 38.51 h at 25 °C; 19.80 h at 35 °C; and 3.00 h at 45 °C), respectively. The photolysis half-life of FBEZF in different initial concentrations were 8.77 h at 1.0 mg L-1, 8.35 h at 5.0 mg L-1, and 8.66 h at 10.0 mg L-1, respectively. Results indicated that the degradation of FBEZF followed first-order kinetics, as the initial concentration of FBEZF only had a slight effect on the UV irradiation effects, and the increase in pH and temperature can substantially accelerate the degradation. The hydrolysis Ea of FBEZF was 49.90 kJ mol-1, which indicates that FBEZF belongs to medium hydrolysis. In addition, the degradation products were identified using ultra-high-performance liquid chromatography coupled with an Orbitrap high-resolution mass spectrometer. One degradation product was extracted and further analyzed by ¹H-NMR, 13C-NMR, 19F-NMR, and MS. The degradation product was identified as 2-(4-fluorobenazyl)-5-methoxy-1,3,4-oxadiazole, therefore a degradation mechanism of FBEZF in water was proposed. The research on FBEZF can be helpful for its safety assessment and increase the understanding of FBEZF in water environments.

Keywords: Fubianezuofeng; abiotic degradation; bactericide; kinetics; mechanism; water.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Chromatography, High Pressure Liquid
  • Hydrogen-Ion Concentration
  • Hydrolysis*
  • Mass Spectrometry
  • Oxadiazoles / chemistry*
  • Photolysis*
  • Sulfones / chemistry*
  • Temperature
  • Ultraviolet Rays
  • Water / chemistry*

Substances

  • Anti-Bacterial Agents
  • Oxadiazoles
  • Sulfones
  • fubianezuofeng
  • Water