Transformation of Biocides Irgarol and Terbutryn in the Biological Wastewater Treatment

Abstract

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.

Sensitive voltammetric determination of herbicide terbutryn using solid electrodes based on silver amalgam and boron-doped diamond

“…It was found that TB provided one oxidation peak at the very positive potential values (about ?1950 mV) and this reaction had also irreversible character. The oxidation of TB to the appropriate sulfoxide or sulfone was described in the literature [52].…”

Investigation on the removal of the major cocaine metabolite (benzoylecgonine) in water matrices by UV 254 /H 2 O 2 process by using a flow microcapillary film array photoreactor as an efficient experimental tool

“…TPs for cases where MS spectra are not definitive (Wendel et al, 2014;Luft et al, 2014). Further 321 chemical characterization of transformation products will be done using 2-dimensional NMR 322 spectroscopy on transformation products isolated with preparative-LC, and further mass 323 spectrometry analyses will be performed using targeted MS/MS on selected degradation products.…”

Effect of algal organic matter (AOM) extracted from Microcystis aeruginosa on photo-degradation of Diuron

“…2 and Table 1. Phycocyanin in IOM and FA has been reported to act as a photo-sensitizer under sunlight irradiation and therefore may have facilitated the reactions by producing various ROSs, including 1 DO 2 , Å OH, and excited-state DOM, presumably 3 …”

“…Emerging contaminants, including pharmaceuticals and personal care products (PPCPs), endocrine-disrupting chemicals (EDCs) and biocides, have been frequently detected at alarming concentrations in rivers, lakes and reservoirs [1][2][3][4]. Worse still, many of these contaminants are recalcitrant to the conventional physicochemical processes in wastewater treatment.…”

“…Phycocyanin is a type of water-soluble conjugated biliprotein with a structure similar to a porphyrin and is known to display a wide range of photo-induced activity [19] due to the formation of the triplet excited state of phycocyanin 3 …”