The biocides irgarol and terbutryn enter the wastewater treatment plant (WWTP) via combined sewer systems after leaching from coatings and paints of materials. In this study, the biotransformation of irgarol and terbutryn was examined in aerobic batch experiments with activated sludge taken from the nitrification zone of a conventional WWTP, since currently there is no information about the fate of irgarol and terbutryn in biological wastewater treatment. Both, irgarol and terbutryn were transformed into one main transformation product (TP) following pseudo first-order kinetics. The TPs were tentatively identified by high-resolution mass spectrometry (HR-MS) to be irgarol sulfoxide and terbutryn sulfoxide. The final confirmation of the proposed chemical structures of the TPs was achieved by a comparison of mass spectra and nuclear magnetic resonance (NMR) spectra with those of authentic reference standards (e.g., synthesized). An analytical method for the sensitive quantification of irgarol, terbutryn and their TPs in environmental samples was developed based on solid phase extraction (SPE) and LC tandem MS detection. Irgarol sulfoxide and terbutryn sulfoxide were detected in the effluents (average concentrations up to 22 ng L(-1) and 65 ng L(-1)) of all four investigated WWTPs as well as in streams and small rivers (up to 14 ng L(-1) and 34 ng L(-1)). Luminescent bacteria inhibition test with Vibrio fischeri exhibited that the TPs irgarol sulfoxide and terbutryn sulfoxide feature a similar bacterial toxicity than the parent compounds.
A novel approach was investigated for the assessment of leaching from a one-component polyurethane (1C-PU) coating used for hydraulic structures using nontarget analysis via LC-QTOF-MS. Leaching behavior of the 1C-PU coating was studied using experiments in which the coating was exposed to water for defined periods (6 h, 24 h, 3 d, 14 d). Three hardening durations for the 1C-PU coating were tested (0 h, 24 h, 14 d) as well as two water matrices (ultrapure water and river water), including a successive water renewal. Dissolved organic carbon, total nitrogen bound and nontarget measurements via LC-QTOF-MS showed that under all tested conditions organic substances were leached out of the 1C-PU coating. The shorter the hardening duration and the longer the leaching duration, the higher were the number and quantities of the eluted substances, while the influence of the water matrix was minor with respect to substance elution. Based on the MS spectra from the LC-QTOF-MS measurements, 30 substances released from the 1C-PU coating were tentatively identified. These substances belong to five chemical groups: derivatives of (i) N-(tosyl)carbamate, (ii) p-toluenesulfonamide (PTSA), (iii) 4,4'-methylenediphenyl diisocyanate (4,4'-MDI), (iv) toluenediisocyanate (TDI), and (v) oligo(ethylene) ([CHO]) as well as p-toluenesulfonic acid. The identity of seven substances was confirmed by authentic reference standards, all of which exhibited an elevated bacterial toxicity to Aliivibrio fischeri. p-Toluenesulfonic acid was present in a German canal (Teltowkanal) with concentrations of up to 11 μg L.
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