TFM (3-Trifluoromethyl-4-nitrophenol)
CAS No. 88-30-2


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Adverse Effects

ACTIVITY: Lampricide, Piscicide


Adverse Effects:

Body Weight Decrease
Endocrine: Altered Sex Ratio
Endocrine: Disruptor

Environmental Effects:

Dramatic altered sex ratio of Sea Lamprey from male to female .

TFM is over 50 times more toxic in water at pH 6.5 than at pH 9.5

TFM is expected to remain in solution in the lake system and persist for long periods of time... TFM is chemically and biologically very stable. An examination of its structure, i.e., aromatic, fluoro-containing, m-substituted phenol, shows that the compound possesses many of the chemical features known to impart persistence to organic compounds.

When TFM is used, amphibians have regularly been found dead in creeks immediately after treatment in Lake Erie watersheds and elsewhere in the Great Lakes.

Regulatory Information
(only comprehensive for the US)
US EPA Registered: Yes 
US EPA PC Code: 036201 
California Chemical Code 5062 
First approval date for use in the U.S.: August 21, 1964
1958 is cited for use in the Great Lakes
Registered use in 
Canada, US  
Other Information
Molecular Formula: C7 H4 F3 NO3 

In Canada, as of 2004:
Clariant Corporation,
Kinetic Industries Inc. US Fish & Wildlife Service

Clariant International (Germany)
H & S Chemical
Sherwin Williams Chemicals
Other Names: 

Products in Canada:
Lamprecid Technical (PCP 25287)
Sea Lamprey Larvicide Lamprecid (PCP 11763)
Lampricide Sea Lamprey Larvicide (PCP 21124)

Case 3082
4-nitro-3-(trifluoromethyl) phenol
Sea Lamprey Larvicide
Alpha, alpha, alpha-trifluoro-4-nitro-meta-cresol

Of special interest:
PAN Data
May 14, 2004: Canada. Re-evaluation. Proposed Acceptablity for Continuing Registration. Report No. PACR2004-11. Canada has based it's approval for continued use on US EPA's RED (see below).
Nov 1999 - US EPA RED (Reregistration Eligibility Decision) 
VERMONT: Brief overview of actions  
NEW YORK: Brief overview of actions 
Note: TFM is the main chemical used to kill sea lamprey larvae in tributaries to the Great Lakes, the Finger Lakes, and Lake Champlain. Since 1958, TFM has been used in the tributaries of the Great Lakes on a rotational basis. The Sea Lamprey Control Program is the responsibility of the Great Lakes Fishery Commission, but it is delivered by Fisheries and Oceans in Canada and the Fish and Wildlife Service in the United States. Since March 1990 the U.S. Fish and Wildlife Services are the only "approved company" to use this lamprecide. 
Undated - Fact sheet 4. TFM and SEA LAMPREY CONTROL. A Success Story. Why use TFM? Great Lakes Fishery Commission, Ann Arbor, Michigan.  
September 13, 2002 - Vermont court decision by William K. Sessions III, Chief Judge, U. S. District Court. Plaintiffs: VT Public Interest Research Group, National Audubon Society, and Sylvia Knight vs. US Fish and Wildlife Service.  
See reports from Great Lakes Fishery Commission's Sea Lamprey Research Program 
1990-91 - SEA GRANT PROJECT SUMMARY. Good overview of the lamprey. 
Great Lakes Fishery Commission. Program Requirements and Cost Estimates for Fiscal Year 2002. Submitted to the governments of Canada and the United States.  
1984 -2002. Sea Lamprey Management costs of the Great Lakes Fishery Commission. 
October 30, 2001 - Plan to release TFM into Vermont Rivers draws lawsuit over possible environmental and health impacts. Vermont Public Interest Research Group. 
2002 - Project Completion Report. Genetic assignment of larval parentage as a means of assessing mechanisms underlying adult reproductive success and larval dispersal by: K.T. Scribner and M.L. Jones. GREAT LAKES FISHERY COMMISSION  
2002 - Studies on the role of sperm-activating proteins and the mechanism of protease-inhibitor(s) reaction for controlling fertilization in sea lamprey by Konrad Dawbrowski and Andrzej Ciereszko. Great Lakes Fishery Commission 2001 Project Completion Report. 
2001 - Compensatory Mechanisms in Great Lakes Sea Lamprey Populations: An Integrated Program of Research and Assessment by Michael L. Jones and Amy L. Derosier. Great Lakes Fishery Commission Project Completion Report. 
2001 - Comparison of larval sea lamprey (Petromyzon marinus) population dynamics in lampricide treated and untreated tributaries of Lake Champlain by Adam Zerrenner and J. Ellen Marsden. Great Lakes Fishery Commission 2001 Project Completion Report.  
2001 - Application of Decision Analysis to Great Lakes sea lamprey management by: M. Jones and S. Haeseker. Great Lakes Fishery Commission 2001 Project Completion Report.
2000 - Collection of Lamprey Brains and Pituitaries for Purification of Hormones by: S. Sower, L. Hanson, and J. Bence. GREAT LAKES FISHERY COMMISSION 2000 Project Completion Report. 
2000 - Large-Scale Production of Petromyzonol Sulfate From Lamprey Liver Cell Cultures and Culture of Sea Lamprey Pituitary Cells by Paul Collodi. Great Lakes Fishery Commission 2001 Project Completion Report.  
2000 - Contaminant Burdens in Great Lakes Sea Lamprey: A 1998 Spatial Survey by: D.M Whittle. GREAT LAKES FISHERY COMMISSION 2000 Project Completion Report 
1999 - Chosing TFM or a Barrier With the Net Present Cost Method by Ted Cowan. GREAT LAKES FISHERY COMMISSION 1999 Project Completion Report 
July 1990 - Resistance to 3-trifluoromethyl-4-nitrophenol (TFM) in sea lamprey. Ronald J. Scholefield and James G. Seelye. National Fishery Research Center Hammond Bay Biological Station Millersburg, Michigan. Effects of changes in dissolved oxygen on the toxicity of 3-trifluoromethyl-4-nitrophenol (TFM) to sea lamprey and rainbow trout. James G. Seelye and Ronald J. Scholefield. Technical Report No. 56. Great Lakes Fishery Commission. Ann Arbor, Michigan. 
May 1961 - Use of 3-trifluormethyl-4-nitrophenol as a selective sea lamprey larvicide; by Vernon C. Applegate, John H. Howell, James W. Moffett. United States Bureau of Commercial Fisheries; B. G. H. Johnson; Fisheries Research Board of Canada; and Manning A. Smith, Dept. of Chemistry, Bucknell University. TECHNICAL REPORT No. 1. GREAT LAKES FISHERY COMMISSION 1451 Green Road P.O. Box 640 Ann Arbor, Michigan 
US EPA Index of Cleared Science Reviews. 

Food Tolerances: From the Table below, approximately 400,000 pounds of TFM were put into streams, creeks, and lakes in the Great Lakes Basin between 1993-1997. Many of these areas are prime fishing spots. Yet, there are no tolerances for TFM in the US because EPA considers the use of this compound to be non-food: "Based on current use pattens and exposure profiles, residues in and on food and/or feed or in drinking water are not expected to occur. Therefore, a dietary risk assessment is not required (Nov 1999 EPA RED)."

Table 1: Summary of TFM use by the USFWS in the Great Lakes Region (1993-1997)
Ref: US EPA RED, November 1999
Lake 1993 1994 1995 1996 1997
pounds active ingredient used
Superior 6,717 19,991 15,997 12,083 18,768
Michigan 18,150 31,219 25,507 29,811 22,959
Huron 40,371 26,953 24,065 14,605 27,926
Erie 0 9,561 414 5,981 2,815
Ontario 9,438 7,026 10,307 11,001 6,442
Total 74,676 94,750 76,290 73,481 78,910

The lampricide 3-trifhtoromethyl-4-nitrophenol (TFM) was developed by the U.S. Fish and Wildlife Service at the Hammond Bay Biological Station where 6,000 chemical compounds were screened in search of a selective toxicant (Applegate et al. 1957). Lampricide treatments of Lake Superior tributaries began in 1958 (Applegate et al. 1961), and 72 of the most-heavily infested streams were treated by

Between 1958 and 1992, 857 lampricide applications were made on 43 streams in Canada (280 treatments) and 84 streams in the United States (577 treatments). Approximately 20% of these streams were treated only once, but some were treated as many as 23 times. During the past ten years, treatments have been conducted regularly on 32 tributaries in Canada and 44 tributaries in the United States. In addition to stream treatments, lentic areas off the mouths of 13 Canadian rivers have been treated with granular Bayer 73.
Ref: Hansen, M. J. [ED.]. 1994. The state of Lake Superior in 1992. Great Lakes Fish. Comm. Spec. Pub. 94-l. 3110 p. Also available at:

Effects on fish TFM became a concern in 1992, when Fisheries and Oceans staff identified previously undetected metabolic effects in fish at sites that had been treated. The Commission responded quickly, helping to fund research by Fisheries and Oceans. The research found that the TFM batches contained trace amounts of dioxin. Though it was not the most toxic form, fish are known to be sensitive to dioxins, especially in their developmental stages. The source of the dioxin was traced to a by-product of the chemical's production, and concentrations varied widely from one batch to another. The research led to a change in the manufacturing process, and the Commission now requires manufacturers to produce TFM without dioxins.
Ref: The importance of maintaining up-to-date information on the environmental impacts of pesticide use for sea lamprey control

... The sensitivity of mudpuppies, frog tadpoles, and adult frogs to use of 3-trifluoromethyl-4- nitrophenol (TFM) in the Great Lakes has been noted on many occasions. TFM has been used annually since 1958 for the control of sea lampreys throughout the Great Lakes. Amphibians regularly have been found dead in creeks immediately after TFM treatment (Gilderhus and Johnson 1980, Matson 1990). Laboratory tests have confirmed that species native to the Great Lakes Basin, such as the grey tree frog, northern leopard frog, and bullfrog, are sensitive to levels of TFM used for sea lamprey control (Chandler and Marking 1975). Mudpuppy population size decreased by a minimum of 29 per cent after a spray event in the Grand River of Ohio (Matson 1990)... Ref: Conservation Priorities for the Amphibians and Reptiles of Canada. Sept 2000 report published by World Wildlife Fund Canada and Canadian Amphibian and Reptile Conservation Network. Prepared by David Seburn and Carolyn Seburn.

Label for TFM: 2004. Canada's Pest Management Authority stated:

"The Canadian labels of all TFM end-use products must be amended to include the following statements to protect workers and the environment."

In the "Environmental Hazards" section:

“This chemical is toxic to fish and aquatic invertebrates. Non-target aquatic organisms may be killed at rates recommended on this label.”
“The directions for use must be strictly followed to minimize hazards to non-target organisms. Do not contaminate water when cleaning equipment or disposing of equipment washwater.”
“Local and appropriate provincial pesticide regulatory authorities must be consulted about use permits that may be required before product is applied.”
“Municipalities that use streams requiring treatment as potable water sources must be notified of the impending treatment at least 24 hours prior to application.”
“Agricultural irrigators that use streams requiring treatment as a source of irrigation water must be notified of the impending treatment at least 24 hours prior to application. Agricultural irrigators must turn off their irrigation systems during treatment and for a 24 hour period aftertreatment.”

In the “Directions for Use” section:

“Do not apply this product by air.”

In the “Precautions” section:

“Wear a long sleeved shirt, long pants, rubber boots with socks, chemical
resistant gloves, a chemical resistant apron or chemical resistant coveralls
and a face shield during mixing, loading, application, clean up, repair and
other handling activities.”

“Users should wash hands before eating, drinking, chewing gum, using
tobacco, or using the toilet.”

“Users should remove clothing/personal protective equipment immediately
if pesticide comes in contact with skin through soaked clothing or spills.
Then wash skin thoroughly and put on clean clothing. Wash contaminated
clothing before reuse.”
“Users should remove personal protective equipment immediately after
handling this product. Wash the outside of gloves before removing. As
soon as possible, wash thoroughly and change into clean clothing.”
“Do not apply this product in a way that will contact workers or other
persons, either directly or through drift.”

Great Lakes Fishery Commission Fact Sheets, online August 2004:  

Fact Sheet 3: What are sea lampreys? How did sea lampreys spread into the Great Lakes?

Fact Sheet 4: TFM and sea lamprey control. A success story. Why use TFM.

Fact Sheet 5: Sea lamprey barriers. New technologies help solve an old problem.

Fact Sheet 6: Sterile-Male-Release-Technigue. An innovative sea lamprey control method.

US Federal Register
Date Published Docket Identification Number Details
April 4, 2002 OPP-2002-0010 Revocation of exemption from the requirement of a tolerance for the "inert" dimethylformamide when used by the U.S. Department of Interior, Fish and Wildlife Service as a solvent for the lamprecide sodium salt of alpha, alpha, alpha-trifluoro-4-nitro-meta-cresol or 4-nitro-3-(trifluoromethyl) phenol (TFM) in the Great Lakes. FINAL RULE.
Nov 1, 2001 na Lake Champlain: Record of decision on Sea Lamprey Control Program.
March 15, 2001 na Lake Champlain: availability of a Draft Supplemental Environmental Impact Statement (DSEIS) To Evaluate Continued Sea Lamprey Control in Lake Champlain.
Dec 22, 1999 na Lake Champlain: public scoping meetings on supplemental environmental impact statement for a sea lamprey control proposal.
Dec 3, 1999 OPP-34210 Availability of Reregistration Eligibility Decision Document for Comment.

Of Particular Interest:

Endocrine Disruptor
From the November 1999 US EPA's Reregistration Eligibility Decision (RED) for TFM

... TFM treatments have been associated with induction of hepatic mixed function oxyganase activity and altered levels of circulating steroids in fish and induced hepatic vitellogenesis in primary cultures of rainbow trout hepatocytes (Hewitt et al. 1997). As such, TFM acts as an estradiol agonist and has a demonstrated endocrine disrupting effect. Since the data on various developmental stages represented disjointed acute studies, chronic toxicity data on fish were not available and as such, a fish full life cycle study of both technical grade TFM and TFM/niclosamide mixture is required to address this deficiency.

... Abundance of sea lamprey peaked in several Great Lakes before chemical control began. The sex ratio in these peak populations were predominately males (68-71%). Following a decade of lampricide treatments, populations of sea lampreys showed marked declines and the sex ratios in these populations shifted toward a predominance of females accounting for 72% of the population (Henrich, et al, 1979). This publication by Henrich concludes that lampricides reduced the populations of sea lampreys in the Great Lakes and contributed to the sequential shifting of the sex composition from a predominance of males to a predominance of females. There are no data to support that the endocrine mediated effect associated with TFM is related to the observed sex-ratio shifts among TFM-treated populations of sea lamprey [page 23].

... Exposure to TFM during embryonic development increased the frequency of abnormalities that lead to increased mortalities and stream treatments with lampricides have resulted in a shift in sex ratios among lampreys over a 16-yr period. TFM treatments have been associated with induction of hepatic mixed function oxyganase activity and altered levels of circulating steroids in fish and induced hepatic vitellogenesis in primary cultures of rainbow trout hepatocytes. As such, TFM acts as an estradiol agonist and has a demonstrated endocrine disrupting effect. The potential for TFM to result in endocrine disrupting effects on fish populations in treatment areas has been considered remote based on the fact that streams are treated at most once every 3 to 5 years, exposure duration is less than 24 hours and TFM has not been demonstrated to persist in treatment areas (Hewitt et al. 1998). However, the duration of exposure to fish downstream of the application site has not been adequately characterized and thus the potential for an endocrine disrupting effect cannot be dismissed [page 42]...

TFM is chemically and biologically very stable. The compound possesses many of the chemical features known to impart persistence to organic compounds... TFM was converted to reduced-TFM with a half-life of less than one week under both aerobic and anaerobic aquatic metabolism conditions. It must be stressed that when reduced-TFM is reported as a reaction product, degradation has not occurred. TFM has just undergone a chemical reduction and under appropriate conditions, reduced-TFM may be re-oxidized to TFM... TFM is expected to remain in solution in the lake system and persist for long periods of time... TFM (C7 H4 F3 NO3 ; M.W. 207.11) is chemically and biologically very stable. An examination of its structure, i.e., aromatic, fluoro-containing, m-substituted phenol, shows that the compound possesses many of the chemical features known to impart persistence to organic compounds. Its pKa is 6.07 and the effect of pH on the toxicity appears to follow closely to the concentration of the lipid-soluble, free phenol form of TFM. This pH sensitivity is used to maximize effectiveness. As pH increases, toxicity, bioaccumulation, and adsorption to sediment decrease. Aqueous solubility of the sodium salt is 5 g/L.[page 24-25].

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