Identification of photoproducts of florasulam in water using UPLC-QTOF-MS

Abstract

Here, we aimed to investigate florasulam photodegradation in aquatic environments under UV-visible irradiation. LC-MS/MS was used to explore the photolysis kinetics of florasulam degradation with respect to different light source types, florasulam concentrations, water sources, and pH. We also tested whether the addition of the nitrate ions, Fe³⁺, or I⁻ to the reaction solution influences florasulam photolysis kinetics. NO₃⁻ accelerates florasulam degradation at low concentrations (0.01–1 mg L⁻¹), but decreases the process at higher concentrations. At low concentrations (≤ 0.1 mg L⁻¹), Fe³⁺ enhanced florasulam photodegradation obviously. However, the addition of 0.01–10 mg L⁻¹ I⁻ decreased the degradation rate linearly. The florasulam photolysis rates in alkaline and neutral solutions were higher than that in acidic solutions. The florasulam degradation rate under mercury light irradiation was greater than that under xenon light. The rate of florasulam degradation in distilled water was greater than in tap water, lake water, and rice paddy water. As the concentration of florasulam increased, the photodegradation rate decreased. Six kinds of transformation products (TPs) were isolated and identified using UPLC/Q-TOF-MS. Based on these TPs and their evolutionary processes, we inferred the florasulam degradation mechanisms, identifying four possible florasulam degradation pathways. Cleavage of the florasulam sulfonamide bond yielded TPs2. TPs2 was intermolecularly rearranged to form a SO₂ extrusion compound, TPs3. Cleavage of the [C-F] bonds led to the formation of TPsl, TPs4, and TPs5, while hydroxylation led to the formation of TPs6. We then predicted the stability of each of the florasulam TPs in water. TPs2 and TPs3 rapidly degraded after reaching maximum concentration due to poor light stability. TPs4 and TPs6 were more photostable than florasulam (the parent compound) and may be important contributors to water pollution.

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