Photodegradation of fluazaindolizine in water under simulated sunlight irradiation: Identification of transformation products and elucidation of transformation mechanism.

The photodegradation of fluazaindolizine in water was investigated under simulated sunlight irradiation. The effects of solution pH, humic acids (HA), nitrates (NO3-) and Fe(III) ions on photolysis of fluazaindolizine were studied. The results indicated that pH did not significantly affect its photodegradation. At low concentration (up to 5 mg/L), HA slightly facilitated the photodegradation of fluazaindolizine, while at high concentration (10-20 mg/L), HA inhibited its photodegradation. The presence of NO3- (0-10 mg/L) and Fe(III) (0-5 mg/L) noticeably accelerated the photodegradation of fluazaindolizine. Moreover, eleven direct transformation products (TPs) were isolated and identified by liquid chromatography quadrupole time-of-flight mass spectrometry. Density functional theory (DFT) calculation was utilized to characterize molecular property of fluazaindolizine and predict the potentiality of the possible photodegradation reaction. Ultimately, a possible transformation mechanism was proposed based on the identified TPs, degradation profiles and DFT calculation. The predominant photoproduct came from ring opening of imidazole-ring and dechlorination. Other TPs resulted from a series of photochemical reactions involving hydroxyl substitution, ring-opening, cleavage, oxidation and decarboxylation. These results were important in elucidating environmental fate of fluazaindolizine in aquatic system and further environmental risk assessment.