Transformation Products of Organic Contaminants and Residues—Overview of Current Simulation Methods
Abstract
:1. Introduction
2. Methods for Transformation and Analysis
2.1. Metabolism Methods
2.2. Electrochemical-Based Methods
2.3. Photochemical-Based Methods
2.4. Fenton-Based Methods
2.5. Analytical Techniques for TP Identification
3. Transformation Processes of Selected Compound Classes
3.1. Pesticides
3.2. Pharmaceuticals/Drugs
3.3. Brominated Flame Retardants
3.4. Mycotoxins
4. Conclusions and Perspectives
Author Contributions
Funding
Conflicts of Interest
References
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Name of Compound/s | Type of Pesticides | Matrices | TPs Prediction/Authentication Methods | Simulated Transformation Mechanisms | Ref |
---|---|---|---|---|---|
Azoxystrobin Difenoconazole Thiacloprid | fungicide fungicide insecticide | brassica species vegetables (pak choi and broccoli) | Suspect screening, in silico fragmentation and authentic standards | Hydrolysis, hydroxylation, dealkylation (O-, N- & S-), dehydrogenation, glucuronidation, esterification | [47] |
Chlorpyrifos | insecticide | fruits and spices | Synthesis by EC and UV and used for targeted screening | P-oxidation, O-dealkylation, hydrolysis, −Cl +H | [48] |
Ethoxyquin | growth regulator | fish feed | Synthesis by chemical (H2O2 and DPPH) and used for authentication | N-oxide, hydroxylation, O-dealkylation, dimerization, epoxidation, quinone formation | [51] |
Forchlorfenuron | growth regulator | kiwifruit | Comparison with authentic standards | +OH, −Cl +H, N-dealkylation, −Cl +OH, glucuronidation | [52] |
Isoproturon | herbicide | plant leaf | UV and sunlight (untargeted) | Hydroxylation, N-dealkylation | [53] |
Bentazon | herbicide | - | Photocatalysis (TiO2, ZnO) | N-dealkylation, hydroxylation, dimerization | [57] |
Cyprodinil | fungicide | - | UV–Vis | Isomerization, cyclization, hydroxylation | [58] |
Methyl parathion | insecticide | - | MnO2 (chemical) | P-oxidation, hydrolysis, dealkylation | [59] |
Fluopyram | herbicide | - | UV and sunlight (untargeted) | −Cl +H, −Cl +OH, cyclization via −HCl | [60] |
Fluopyram | herbicide | commercially available microsomes | Liver microsomes and EC | Hydroxylation, N-dealkylation, −Cl +H, −Cl +OH, dehydrogenation, epoxidation | [62] |
Chlorpyrifos | insecticide | commercially available microsomes | Liver microsomes and EC | P-oxidation, O-dealkylation, hydrolysis, −Cl +H | [63] |
Metribuzin | herbicide | tomato | Comparison with authentic standards | Deamination, oxidative desulfuration | [65] |
Flonicamid | insecticide | orange | Comparison with authentic standards | Hydrolysis of amides, deamination by hydrolysis | [66] |
Quinoxyfen | fungicide | water | UV and untargeted | −Cl +OH, hydroxylation, cyclization (−H2O, −HCl), hydrolysis | [67] |
DDT and DDT-related cpds | insecticide | dolphin serum | Comparison with authentic standards | Olefin via −HCl, −Cl +OH | [68] |
Drugs | Group of Drugs | TPs Prediction/Authentication Methods | Simulated Transformation Mechanisms * | Toxicity Test of TP | Degra Dation Kinetic | Ref |
---|---|---|---|---|---|---|
Amoxicillin, Cefotaxime, Linezolid, Moxifloxacin, Metronidazole, Fluconazole | Antibiotic Antifungal | EC-reactor RLM In vivo (urine samples) | Red, Deh, Dealk, OH, X-ox, Dehal, GSH Red, Deh, Dealk, OH, X-ox, Dehal, Red, X-ox, OH, Alkyl | [69] | ||
Acebutolol, Atenolol, Propranolol, Pindolol, Oxprenolol, Cicloprolol, Pirbuterol, Mexiletine, Propafenone | β-blocker β2-adrenoceptor Antiarrhythmic | EC-reactor In vivo (urine and plasma samples) | OH, X-ox, Dealk, Alkyl, Red, GSH OH, X-ox, Dealk | [72] | ||
Buspirone Promazine Testosterone 7-ethoxycoumarin | Anxiolytic Antipsychotics Anabolic steroid Test substance (CYP450) | HLM Photocatalytic (TiO2) EC-Fenton EC-Reactor | OH, Deh, X-ox, Dealk, Hyd, OH, Deh, X-ox, Dealk, Hyd OH, Deh, X-ox, Hyd Deh, X-ox, Dealk | [26] | ||
Oxacillin | β-lactam antibiotic | Photocatalytic (TiO2) Sonochemisty EC-reactor Photo-Fenton | X, ox, rCleav, OH X-ox, rCleav X-ox, rCleav X-ox, rCleav, OH | [73] | ||
Trimethoprim | Anti-infective | Electrolysis EC-Fenton EC reactor | OH OH, Dealk OH | [18] | ||
Moclobemide, Toloxatone | Antidepressant | Photocatalytic (TiO2) HLM | X-ox, OH, Dealk, Deh, Dehal, rCleav X-ox, OH, Dealk, Deh | X | [74] | |
Clozapine | Antipsychotic | Photocatalytic (TiO2, ZnO) HLM | X-ox, OH, Hyd, Dealk, Dehal, rCleav X-ox, OH, Hyd, Dealk, Dehal, rCleav | X | [70] | |
Tiapride | Antipsychotic | Photolytic Photocatalytic (TiO2, H2O2) | Dealk, OH, Red, Desulf, X-ox Dealk, OH, Red, Desulf, X-ox, rCleav, Deh | X | X | [75] |
Propranolol | β-blocker | Photolysis | OH, rCleav, X-ox, Ox | X | X | [27] |
Vincristine | Anticancer | Aerobic activated sludge | rCleav, Ox, Deca, Dealk, Deh, | X | [76] | |
Venlafaxine | Antidepressant | Photocatalytic (UV/TiO2) | OH, Alkyl, Deh, X-ox, | X | X | [77] |
Triclosan | Antimicrobial | Electrochemical reactor | OH, Ox, Dehal, Alky | X | [78] | |
Ibuprofen | Nonsteroidal anti-inflammatory | UV/chlorine UV/H2O2 | OH, Decar, Dealk, +Cl, rCleav | X | X | [79] |
Omeprazole | Proton pump inhibitors | Photolysis | Red, Dehyd, OH, Ox | X | X | [80] |
Ifosamine, Cyclophosphamide | Cytostatic | Photocatalytic (TiO2, Pt-TiO2) | OH, Dealk, Ox | X | [81] | |
Amoxicillin, Ampicillin | Antibiotic | Photolysis | OH, Deh, Dealk | X | [82] | |
Carbamazepine | Antiepileptic | UV/chlorine | Red, OH, +Cl, Hyd, Deh | X | X | [83] |
Naproxen | Nonsteroidal anti-inflammatory | UV and solar Photolysis | Dealk, Hydr, OH | X | X | [84] |
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Kotthoff, L.; Keller, J.; Lörchner, D.; Mekonnen, T.F.; Koch, M. Transformation Products of Organic Contaminants and Residues—Overview of Current Simulation Methods. Molecules 2019, 24, 753. https://doi.org/10.3390/molecules24040753
Kotthoff L, Keller J, Lörchner D, Mekonnen TF, Koch M. Transformation Products of Organic Contaminants and Residues—Overview of Current Simulation Methods. Molecules. 2019; 24(4):753. https://doi.org/10.3390/molecules24040753
Chicago/Turabian StyleKotthoff, Lisa, Julia Keller, Dominique Lörchner, Tessema F. Mekonnen, and Matthias Koch. 2019. "Transformation Products of Organic Contaminants and Residues—Overview of Current Simulation Methods" Molecules 24, no. 4: 753. https://doi.org/10.3390/molecules24040753