Biotransformation of benzotriazoles: insights from transformation product identification and compoundspecific
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1 Supporting Information for Biotransformation of benzotriazoles: insights from transformation product identification and compoundspecific isotope analysis Sebastian untscha 1) 2), Thomas ofstetter 1) 2), Emma L. Schymanski 1), Stephanie Spahr 1), Juliane ollender 1) 2)* 1) Eawag, Swiss Federal Institute of Aquatic Science and Technology, 8600 Dübendorf, Switzerland 2) Institute of Biogeochemistry and Pollutant Dynamics (IBP), ET Zurich, 8092 Zurich, Switzerland Corresponding author: Juliane ollender, Tel.: , Fax: Table of Contents Chemicals 2 Details about 4-C 3 -BT and 5-C 3 -BT degradation assays 2 Details about 1-BT degradation assays to apply CSIA 2 Table S1: Physicochemical properties of benzotriazoles 3 Figure S1: Monitored p values and oxygen content during 1-BT degradation. 3 Figure S2: Peak areas of minor candidate TPs from 1-BT degradation 4 Figure S3: Carbon and nitrogen isotope fractionation in activated sludge and filtrate control 4 Table S2: Compounds with reference standards 5 Figure S4: MS/MS spectra of standard compounds and transformation products 6 References 13 1
2 Chemicals Chemicals were purchased in highest available purity from Fluka (Buchs, Switzerland: 1benzotriazole (1-BT)), Sigma-Aldrich (Buchs, Switzerland: 1-methyl-1-benzotriazole; 5-methyl- 1-benzotriazole (5-C 3 -BT); 4-hydroxy-1-benzotriazole; 1-benzotriazole-5-carboxylic acid; 5,6-dimethyl-1-benzotriazole; 1-(methoxymethyl)-1-benzotriazole) and Toronto Research Chemicals (Toronto, Canada: 4-methyl-1-benzotriazole (4-C 3 -BT); 1-benzotriazole-d4; 5- methyl-1-benzotriazole-d6). For preparation of solutions and analysis, methanol ( 99.9%, Merck, Darmstadt, Germany) and ethyl acetate ( 99.7%, Sigma-Aldrich, Steinheim, Germany) were used. Further solutions were formic acid (98-100%, Merck, Darmstadt, Germany), hydrochloric acid (32%, Merck, Darmstadt, Germany) and n-hexane (>96%, Biosolve, Valkenswaard, etherlands). All aqueous solutions were prepared with nanopure water (18.2 MΩ cm, Barnstead AOpure Diamond Water Purification System). Details about 4-C 3 -BT and 5-C 3 -BT degradation assays Batch reactors were prepared by filling 50 ml of activated or sterilized sludge and secondary effluent into 100 ml glass bottles. Experiments were initiated by spiking all reactors with 25 µl of 1 g/l spiking solutions (in methanol) to achieve a final concentration of 500 µg/l (3.8 µm 4-C 3 -BT and 5-C 3 -BT) in each reactor, which were one active reactor and one control of each type per compound. All reactors were covered with perforated parafilm and placed on a shaker table at 160 rpm to provide aeration of the sludge. Ambient temperature was kept constant at 19 ± 1 C. At each sampling step, 1.5 ml of the sludge was withdrawn and filtered through 0.7 µm glass microfiber filters (GF/F, Whatman). Aliquots of 990 µl were stored in the dark at 4 C until LC-R- MS/MS analysis. Details about 1-BT degradation assays to apply CSIA 25 reactors (15 active bioreactors, 5 sterile controls, 5 filtrate controls) were prepared by filling 110 ml of activated, filtered or sterilized sludge into 250 ml glass bottles. The experiment was initiated by spiking all reactors with 110 µl of a 20 mm spiking solution to achieve a final concentration of 20 µm 1-BT (2.4 mg/l) in each reactor. All reactors were covered with perforated parafilm and placed on a shaker table at 160 rpm to aerate the sludge. Ambient temperature was kept constant at 20 ± 1 C. One reactor of the respective setup was processed at a time, according to a predefined sampling schedule. Dissolved oxygen, temperature as well as p of the sludge were determined with a flexible p-oxygen-conductivity meter (Q30d flexi from ach Lange with LDO 101 oxygen probe and p C101 p electrode), before filtering the whole 2
3 p bioreactor content through 0.7 µm glass microfiber filters (GF/F, Whatman). 990 µl of the filtrate were withdrawn for LC-R-MS/MS and spiked with 10 µl of deuterated internal standards (50 mgl -1 1-BT-d4 and 5-C 3 -BT-d6 in methanol) to a final concentration of 500 µgl -1. The p of the remaining filtrate was adjusted to 2.0 ± 0.1 before (SPE) extraction was performed. The extract of the SPE was used for GC-IRMS analysis. Table S1: Physicochemical properties of benzotriazoles Compound CAS no. pk a1 pk a2 logk OW Solubility in water [g/l] c) 1-BT a) 8.27 a) 1.23 b) 28 4-C 3 -BT d) 8.93 d) 1.81 d) 5-C 3 -BT d) 8.86 d) 1.89 b) 7 (TTri) a) Wang et al. (2000) [1] b) art et al. (2004) [2] c) Voutsa et al. (2006) [3] d) Predicted by JChem for Excel 5.6, 2011, ChemAxon Ltd. (Budapest, ungary). TTri = Tolyltriazol = mixture of 4- and 5-C 3 -BT p O 2 Active Bioreactor Sorption Control Abiotic Control O2 [mg/l] Time [days] Figure S1: Monitored p values and oxygen content in active and control bioreactors over the time course of the 1-BT biotransformation experiment. 3
4 d 13 C [ ] Area counts 12x TP1 TP7 TP9 TP10 TP11 TP12 TP13 TP14 TP15 TP16 TP17 TP18 TP21 TP22 TP23 TP24 TP Time [days] Figure S2: Peak areas of minor candidate TPs from 1-BT degradation Activated Sludge Filtrate Control -22 Activated Sludge Filtrate Control d 15 [ ] c/c0 c/c0 Figure S3: Carbon and nitrogen isotope fractionation during 1-BT transformation. o isotope fractionation was observed in filtrate control samples in which 1-BT was not degraded. 4
5 Further compounds with reference standard Identified transformation products Parent compounds Table S2: Compounds with reference standards and their molecular formula, MSMS, retention time (RT), structure, and ChemSpider ID. 1-C 3 -BT, 4-O-BT, and 5-COO-BT were identified as benzotriazole TPs, the MSMS spectra and RT of the other compounds were used for spectral interpretation of candidate TPs. Compound name Molecular formula MS/MS RT Structure ChemSpider ID 1-Benzotriazole C653 [M+]+, ESI +, CD 90%, EA (1-BT) (42%) C (0.3%) C (24%) C (100%) C Methyl-1-benzotriazole C773 [M+]+, ESI +, CD 90%, pos C (4-C 3 -BT) (37%) C (85%) C (29%) C (100%) C Methyl-1-benzotriazole C773 [M+]+, ESI +, CD 90%, EA (5-C 3 -BT) (74%) C65+ 3 C (66%) C (18%) C (29%) C (100%) C Methyl-1-benzotriazole C773 [M+]+, ESI +, CD 105%, pos (1-C 3 -BT) (54%) C (36%) C (70%) C (37%) C652+ C (100%) C ydroxy-1-benzotriazole C653O [M+]+, ESI +, CD 105%, pos O (4-O-BT) (20%) C (100%) C (19%) C55O (52%) C663O+ 1-Benzotriazole-5-carboxylic acid C753O2 [M+]+, ESI +, CD 90%, pos O (5-COO-BT) (38%) C (100%) C56+ O (36%) C (73%) C66O (26%) C ydroxy-1-benzotriazole C653O [M+]+, ESI +, CD 90%, EA (1-O-BT) (5%) C (4%) C (100%) C (15%) C653+ O (26%) C663O+ 1-(Methoxymethyl)-1-benzotriazole C893O [M+]+, ESI +, CD 90%, pos (1-MeOMe-BT) (41%) C (30%) C (37%) C (33%) C (100%) C C O 5,6-Dimethyl-1-benzotriazole C893 [M+]+, ESI +, CD 100%, pos (5,6-DiC 3 -BT) (51%) C65+ 3 C (100%) C (54%) C79+ 3 C (78%) C ,2,3-triazole C233 [M+]+, ESI +, CD 90%, UF (1-1,2,3-T) (100%) C ,2,3-triazole-5-ol C233O [M+]+, ESI +, CD 120%, pos O (5-O-1,2,3-T) (2%) C23O (100%) C243O+ -Methylaniline C79 [M+]+, ESI +, CD 90%, UF C3 (-C 3 -aniline) (100%) C (20%) C710+ 5
6 The following are annotated MS/MS spectra of selected transformation products. All spectra are also available at under the given accession IDs. The records there contain the full measurement details and, where possible, structure names and information. Figure S4a: MS/MS spectrum of TP 28, C Available as MassBank spectrum ETS Figure S4b: MS/MS spectrum of TP 5, C O. Available as MassBank spectrum ETS
7 Figure S4c: MS/MS spectrum of TP 6, C O. Available as MassBank spectrum ETS Figure S4d: MS/MS spectrum of TP 7, C O 2. Available as MassBank spectrum ETS
8 Figure S4e: MS/MS spectrum of TP 8, C O 2. Available as MassBank spectrum ETS Figure S4f: MS/MS spectrum of TP 9, C O 3. Available as MassBank spectrum ETS o structures are proposed for this structure due to insufficient evidence from the MS/MS. 8
9 Figure S4g: MS/MS spectrum of TP 10, C O 3. Available as MassBank spectrum ETS o structures are proposed for this structure due to insufficient evidence from the MS/MS. Figure S4h: MS/MS spectrum of TP 31, C O 2. Available as MassBank spectrum ETS
10 Figure S4i: MS/MS spectrum of TP 18, C O 2. Available as MassBank spectrum ETS o structures are proposed for this structure due to insufficient evidence from the MS/MS. Figure S4j: MS/MS spectrum of TP 19, C O 2. Available as MassBank spectrum ETS o structures are proposed for this structure due to insufficient evidence from the MS/MS. 10
11 Figure S4k: MS/MS spectrum of TP 20, C O 4. Available as MassBank spectrum ETS o structures are proposed for this structure due to insufficient evidence from the MS/MS. Figure S4l: MS/MS spectrum of TP 21, C O 4. Available as MassBank spectrum ETS o structures are proposed for this structure due to insufficient evidence from the MS/MS. 11
12 Figure S4m: MS/MS spectrum of TP 42, C O 2. Available as MassBank spectrum ETS o structures are proposed for this structure due to insufficient evidence from the MS/MS. Figure S4n: MS/MS spectrum of TP 22, C O 2. Available as MassBank spectrum ETS
13 Figure S4o: MS/MS spectrum of TP 23, C O 2. Available as MassBank spectrum ETS The MS/MS spectra of the additional compounds in Table S2 are also available on MassBank, accession IDs ETS00115 to ETS References 1. Wang,.; Burda, C.; Persy, G.; Wirz, J., Photochemistry of 1-benzotriazole in aqueous solution: A photolatent base. Journal of the American Chemical Society 2000, 122, (24), art, D. S.; Davis, L. C.; Erickson, L. E.; Callender, T. M., Sorption and partitioning parameters of benzotriazole compounds. Microchemical Journal 2004, 77, (1), Voutsa, D.; artmann, P.; Schaffner, C.; Giger, W., Benzotriazoles, alkylphenols and bisphenol A in municipal wastewaters and in the Glatt River, Switzerland. Environmental science and pollution research international 2006, 13, (5),
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