TFM

• CAT Number: I037163
• CAS Number: 88-30-2
• Molecular Formula: C7H4F3NO3
• Molecular Weight: 207.11
• Purity: 98%
• Synonyms: TFM; NSC 59758; NSC59758; NSC-59758; 3-(Trifluoromethyl)-4-Nitrophenol
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: -20°C
• IUPAC Name: 4-nitro-3-(trifluoromethyl)phenol
• InChI: InChI=1S/C7H4F3NO3/c8-7(9,10)5-3-4(12)1-2-6(5)11(13)14/h1-3,12H
• InChIKey: ZEFMBAFMCSYJOO-UHFFFAOYSA-N
• SMILES: OC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1

TFM（Cat No.:I037163）, also known as 3-trifluoromethyl-4-nitrophenol (CAS 88-30-2), is a chemical compound belonging to the phenol class. It is primarily used as a molluscicide, specifically to control snails and slugs. TFM acts by interfering with the metabolism and physiology of these mollusks, leading to their elimination. It finds application in various environments, including aquatic systems, to manage snail-borne diseases and control invasive mollusk populations. As a pesticide, TFM plays a crucial role in safeguarding agricultural crops, protecting public health, and preserving the balance of ecosystems affected by mollusk infestations.

Reference

1: Dinehart S, Hubert TD. Investigation on Endocrine Disruption of the Larval Lampricide 3-Trifluoromethyl-4-Nitrophenol: Short-Term Reproduction Assay with Fathead Minnow (Pimephales promelas). Environ Toxicol Chem. 2020 Aug;39(8):1599-1607. doi: 10.1002/etc.4751. Epub 2020 Jun 15. PMID: 32418241.
2: Huerta B, Chung-Davidson YW, Bussy U, Zhang Y, Bazil JN, Li W. Sea lamprey cardiac mitochondrial bioenergetics after exposure to TFM and its metabolites. Aquat Toxicol. 2020 Feb;219:105380. doi: 10.1016/j.aquatox.2019.105380. Epub 2019 Dec 12. PMID: 31855722.
3: Hepditch SLJ, Tessier LR, Wilson JM, Birceanu O, O’Connor LM, Wilkie MP. Mitigation of lampricide toxicity to juvenile lake sturgeon: the importance of water alkalinity and life stage. Conserv Physiol. 2019 Dec 8;7(1):coz089. doi: 10.1093/conphys/coz089. PMID: 31832194; PMCID: PMC6900748.
4: Christie MR, Sepúlveda MS, Dunlop ES. Rapid resistance to pesticide control is predicted to evolve in an invasive fish. Sci Rep. 2019 Dec 3;9(1):18157. doi: 10.1038/s41598-019-54260-5. PMID: 31796760; PMCID: PMC6890735.
5: Pike SJ, Lavagnini E, Varley LM, Cook JL, Hunter CA. H-Bond donor parameters for cations. Chem Sci. 2019 May 16;10(23):5943-5951. doi: 10.1039/c9sc00721k. PMID: 31360400; PMCID: PMC6566073.
6: Wilkie MP, Hubert TD, Boogaard MA, Birceanu O. Control of invasive sea lampreys using the piscicides TFM and niclosamide: Toxicology, successes & future prospects. Aquat Toxicol. 2019 Jun;211:235-252. doi: 10.1016/j.aquatox.2018.12.012. Epub 2018 Dec 21. PMID: 30770146.
7: Vo NTK, Seymour CB, Mothersill CE. The common field lampricide 3-trifluoromethyl-4-nitrophenol is a potential radiosensitizer in fish cells. Environ Res. 2019 Mar;170:383-388. doi: 10.1016/j.envres.2018.12.060. Epub 2018 Dec 26. PMID: 30623885.
8: Hinkle KL, Olsen D. Exposure to the lampricide TFM elicits an environmental stress response in yeast. FEMS Yeast Res. 2019 Jan 1;19(1):foy121. doi: 10.1093/femsyr/foy121. PMID: 30445546; PMCID: PMC6455944.
9: Birceanu O, Wilkie MP. Post-exposure effects of the piscicide 3-trifluoromethyl-4-nitrophenol (TFM) on the stress response and liver metabolic capacity in rainbow trout (Oncorhynchus mykiss). PLoS One. 2018 Jul 23;13(7):e0200782. doi: 10.1371/journal.pone.0200782. PMID: 30036372; PMCID: PMC6056040.
10: Vo NTK, Moore LC, Spiteri KW, Hanner R, Wilkie MP, DeWitte-Orr SJ. Assessing off-target cytotoxicity of the field lampricide 3-trifluoromethyl-4-nitrophenol using novel lake sturgeon cell lines. Ecotoxicol Environ Saf. 2018 Oct 30;162:536-545. doi: 10.1016/j.ecoenv.2018.07.017. Epub 2018 Jul 17. PMID: 30016760.
11: Bussy U, Chung-Davidson YW, Buchinger T, Li K, Smith SA, Jones AD, Li W. Metabolism of a sea lamprey pesticide by fish liver enzymes part A: identification and synthesis of TFM metabolites. Anal Bioanal Chem. 2018 Feb;410(6):1749-1761. doi: 10.1007/s00216-017-0830-8. Epub 2017 Dec 28. PMID: 29282500.
12: Bussy U, Chung-Davidson YW, Buchinger T, Li K, Smith SA, Daniel Jones A, Li W. Metabolism of a sea lamprey pesticide by fish liver enzymes part B: method development and application in quantification of TFM metabolites formed in vivo. Anal Bioanal Chem. 2018 Feb;410(6):1763-1774. doi: 10.1007/s00216-017-0831-7. Epub 2017 Dec 26. PMID: 29279987.
13: Tessier LR, Long TAF, Wilkie MP. Influence of body size, metabolic rate and life history stage on the uptake and excretion of the lampricide 3-trifluoromethyl-4-nitrophenol (TFM) by invasive sea lampreys (Petromyzon marinus). Aquat Toxicol. 2018 Jan;194:27-36. doi: 10.1016/j.aquatox.2017.10.020. Epub 2017 Oct 28. PMID: 29132032.
14: McConville MB, Mezyk SP, Remucal CK. Indirect photodegradation of the lampricides TFM and niclosamide. Environ Sci Process Impacts. 2017 Aug 16;19(8):1028-1039. doi: 10.1039/c7em00208d. PMID: 28675238.
15: Hlina BL, Tessier LR, Wilkie MP. Effects of water pH on the uptake and elimination of the piscicide, 3-trifluoromethyl-4-nitrophenol (TFM), by larval sea lamprey. Comp Biochem Physiol C Toxicol Pharmacol. 2017 Oct;200:9-16. doi: 10.1016/j.cbpc.2017.05.005. Epub 2017 Jun 3. PMID: 28587838.
16: McConville MB, Cohen NM, Nowicki SM, Lantz SR, Hixson JL, Ward AS, Remucal CK. A field analysis of lampricide photodegradation in Great Lakes tributaries. Environ Sci Process Impacts. 2017 Jul 19;19(7):891-900. doi: 10.1039/c7em00173h. PMID: 28561092.
17: McConville MB, Hubert TD, Remucal CK. Direct Photolysis Rates and Transformation Pathways of the Lampricides TFM and Niclosamide in Simulated Sunlight. Environ Sci Technol. 2016 Sep 20;50(18):9998-10006. doi: 10.1021/acs.est.6b02607. Epub 2016 Aug 26. PMID: 27508405.
18: Sakamoto K, Dew WA, Hecnar SJ, Pyle GG. Effects of Lampricide on Olfaction and Behavior in Young-of-the-Year Lake Sturgeon (Acipenser fulvescens). Environ Sci Technol. 2016 Apr 5;50(7):3462-8. doi: 10.1021/acs.est.6b01051. Epub 2016 Mar 25. PMID: 27015540.
19: Hinkle KL, Anderson CC, Forkey B, Griffin J, Cone K, Vitzthum C, Olsen D. Exposure to the lampricide 3-trifluoromethyl-4-nitrophenol results in increased expression of carbohydrate transporters in Saccharomyces cerevisiae. Environ Toxicol Chem. 2016 Jul;35(7):1727-32. doi: 10.1002/etc.3314. Epub 2016 Mar 29. PMID: 26606276; PMCID: PMC5076018.
20: Bussy U, Chung-Davidson YW, Li K, Li W. A quantitative assay for reductive metabolism of a pesticide in fish using electrochemistry coupled with liquid chromatography tandem mass spectrometry. Environ Sci Technol. 2015 Apr 7;49(7):4450-7. doi: 10.1021/es5057769. Epub 2015 Mar 11. PMID: 25730707.