3-(Trifluoromethyl)-4-nitrophenol

207.11

207.11

2053698

201-818-2

96W52A3IFS

59758

DTXSID7021788

Yellow to orange crystalline solid

2908999090

66

2.87 (est)

Yellow Crystalline Powder

1.6±0.1 g/cm3

76 °C

135-138 °C0.01 mm Hg(lit.)

135-138°C/0.01mm

1.507

In water, 5000 mg/L at 25 deg C

Combustible. Do not use and store near open flame. Store only in original cotainer, in a dry place inaccessible to children, pets and domestic animals. /Sea Lamprey Larvicide/

1.3X10-3 mm Hg at 25 deg C (est)

Celiac-rat LDL0: 40 mg/kg; Celiac-mouse LD50: 25 mg/kg

Flammable; combustion produces toxic nitrogen oxides and fluoride gases

Henry's Law constant = 1.9X10-8 atm-cu m/mole at 25 °C (est)

pKa = 6.07

Hydroxyl radical reaction rate constant = 7.7X10-13 cu cm/molec-sec at 25 °C (est)

III

6.1(b)

2588

3

20/21/22-36/37/38

26-28-36/37/39-45

GP3520000

Xn,Xi

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Irritant

P261-P280-P305 + P351 + P338

H302-H312-H315-H319-H332-H335

Do not contaminate water, food, or feed by storage or disposal. Open dumping is prohibited. Pesticide Disposal: LAMPRICIDE spray mixture or rinsate that cannot be used or chemically reprocessed should be disposed of in a landfill approved for pesticides or buried in a safe place away from water supplies. Container Disposal: Triple rinse (or equivalent) container and then offer for recycling, reconditioning, or disposal in approved landfill or bury in a safe place. Consult federal, provincial, state, or local authorities for approved alternative procedures. /Sea Lamprey Larvicide/|Do not contaminate water, food, or feed by storage or disposal. PESTICIDE DISPOSAL: Pesticide wastes are acutely hazardous. Improper disposal of excess pesticide, spilled bait, or rinsate is a violation of Federal law. If these wastes cannot be disposed of according to instructions in the application manual, contact your State Pesticide or Environmental Control Agency, or the Hazardous Waste representative at the nearest EPA Regional Office for guidance. CONTAINER DISPOSAL: Dispose of empty plastic wrappers and packing cartons in a sanitary landfill, or if allowed by state and local authorities, by burning. If burned, stay out of smoke.|This chemical is toxic to fish and aquatic invertebrates. Nontarget organisms (such as freshwater clams and mussels) may be killed at recommended rates. Directions for use must be strictly followed to minimize hazards to nontarget organisms. Do not contaminate water by the cleaning of equipment or disposing of equipment washwaters or waste. /TFM-BAR and Sea Lamprey Larvicide/|SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - 3-Trifluoro-Methyl-4-Nitro-Phenol and Niclosamide p.184 EPA 738-R-99-007 (November 1999) This document contains the reregistration eligibility decisions for two compounds which are used alone or in combination against the same pest. TFM is the main chemical used to kill sea lamprey larvae in tributaries to the Great Lakes, the Finger Lakes, and Lake Champlain. Niclosamide is used to kill sea lamprey larvae in combination with TFM.[Available from, as of March 1, 2007: http://www.epa.gov/pesticides/reregistration/status.htm]

|Danger|H301 (19.61%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P310, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 51 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Handlers must wear: Protective eyewear (goggles, face shield, or safety glasses);Long-sleeved shirt and long pants; Chemical-resistant gloves (such as Natural Rubber, selection Category A); Socks and shoes /TFM-BAR/|Handlers must wear: coveralls or rubber apron over long-sleeved shirt and long pants; chemical-resistant gloves (such as barrier laminate, butyl rubber, nitrile rubber, neoprene rubber, or polyvinyl chloride (PVC), Viton); chemical-resistant footwear plus socks; and protective eyewear (googgles or face shield). Applicators who apply diluted product must wear chemical-resistant gloves (such as barrier laminate, butyl rubber, nitrile rubber, neoprene rubber, or polyvinyl chloride (PVC), Viton) /Sea Lampry Larvicide/

Handle and open container in a manner that will prevent spillage. If the container is leaking or material is spilled for any reason or cause, contain spill with a barrier of absorbent material. Refer to Precautionary Statements on label for hazards associated with the handling of this material. Do not walk through spilled material... In spill or leak incidents, keep unauthorized people away. /Sea Lamprey Larvicide/

Restricted Use Pesticide. Due to Acute Eye Irritation, Acute Oral Toxicity and Aquatic Organism Toxicity. Need for Specialized Equipment and Highly Specialized Applicator Training. For retail sale to, and use only by, USD1, EWS, State Fish and Game, Fisheries and Oceans Canada, and Provincial Certified Applicators trained in sea lamprey control or persons under their direct supervision. /TFM-BAR/|Restricted Use Pesticide. Due to acute hazards to the eye and skin and to non-target organisms, need for highly specialized applicator training, and need for specialized equipment. Only for sale to and application by certified applicators of the U.S. Fish and Wildlife Service, Fisheries and Oceans Canada and Provincial and State Fish and Game employees. /TFM-HP Sea Lamprey Larvicide/|Municipalities that use streams requiring treatment as potable water sources must be notified of impending treatment at least 24 hours prior to application. ... Agricultural irrigators must turn off their irrigation system for a 24-hour period during and after treatment. /TFM-BAR and Sea Lamprey Larvicide/|User Safety Requirements: Follow manufacturers instructions for cleaning/maintaining PPE. If no such instructions are provided for washables, use detergent and hot water. Keep and wash PPE separately from other laundry. /TFM-BAR and Sea Lamprey Larvicide/|For more Preventive Measures (Complete) data for 4-NITRO-3-TRIFLUOROMETHYLPHENOL (6 total), please visit the HSDB record page.

most toxic

LD50 Rat oral 160 mg/kg (males) and 141 mg/kg (females)|LD50 Rabbit dermal >2,000 mg/kg

/AQUATIC SPECIES/ Acute toxicity of TFM ranges from being slightly toxic to highly toxic for freshwater fish species. The most sensitive species tested was the channel catfish, Ictalurus punctatus (96 hour LC50 = 0.60 mg/L in soft, reconstituted well water, pH 7.2 to 7.6), while the least sensitive species tested was the bluegill sunfish, Lepomis macrochirus (96 hour LC50 = 37 mg/L in hard well water, pH 8.3 to 8.5).|/AQUATIC SPECIES/ ... All the early developmental stages of walleye (Stizostedion vitreum) from gametes to sac fry were more resistant to TFM than were similar developmental stages of sea lamprey larvae. ... The toxicity of TFM to six developmental stages of the rainbow trout /was examined/ and ... sac fry were the most sensitive life stage studied. Exposure to TFM during sea lamprey /target species/ embryonic development increased the frequency of abnormalities that lead to increased mortalities.|/AQUATIC SPECIES/ 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.|/AQUATIC SPECIES/ In acute toxicity tests, TFM was moderately to slightly toxic to aquatic invertebrates (24 hour LC50 range: 3.8 to 22.3 mg/L). When TFM is used in combination with niclosamide (98:2 by weight), LC50 values for the mixture ranged from 1.5 mg/L (moderately toxic) to greater than 100.0 mg/L (practically non-toxic). The most tolerant species tested were crayfish, dragonflies, snipeflies, and dobsonflies. The most sensitive species were snails and aquatic earthworms.|For more Ecotoxicity Excerpts (Complete) data for 4-NITRO-3-TRIFLUOROMETHYLPHENOL (6 total), please visit the HSDB record page.

3-Trifluoromethyl-4-nitrophenol's production may result in its release to the environment through various waste streams; its use as a lampricide to eradicate the parasitic sea lamprey (1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values in the range of 224-390 at pH 6, and 38-52 at pH 8(2), indicates that 3-trifluoro-methyl-4-nitro-phenol is expected to possess moderate mobility in soil under acidic conditions and high to very high mobility under alkaline conditions(SRC). 3-Trifluoromethyl-4-nitrophenol is a weak acid with pKa of 6.07(3), indicating that it will partially exist as its conjugate base (anion) under environmental conditions. The Henry's Law constant for the free acid (neutral species) is estimated as 1.9X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(4). Volatilization from moist soil surfaces is not expected to be an important environmental fate process based on the Henry's Law constant for the neutral species of 3-trifluoromethyl-4-nitrophenol and the fact that anions do not volatilize(SRC). Volatilization from dry soil surfaces is not expected(SRC), based upon an estimated vapor pressure of 1.3X10-3 mm Hg determined from a fragment constant method(5). The biodegradation half-life of 3-trifluoromethyl-4-nitrophenol under aerobic and anaerobic conditions was under 1 week, with 4-amino-3-(trifluoromethyl)phenol observed as the primary degradation product(2).|AQUATIC FATE: Based on a classification scheme(1), Koc values in the range of 224-390 at pH 6, and 38-52 at pH 8(2), indicates that 3-trifluoro-methyl-4-nitro-phenol is not expected to adsorb to suspended solids and sediment under alkaline conditions, but may adsorb under acidic conditions(SRC). 3-Trifluoromethyl-4-nitrophenol is a weak acid with pKa of 6.07(3), indicating that it will partially exist as its conjugate base (anion) under environmental conditions(SRC). The Henry's Law constant for the free acid (neutral species) is estimated as 1.9X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(4). Volatilization from water surfaces is not expected to be an important environmental fate process based on the Henry's Law constant for the neutral species of 3-trifluoromethyl-4-nitrophenol and the fact that anions do not volatilize(SRC). According to a classification scheme(5), a BCF of 8.4 measured in rainbow trout(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The biodegradation half-life of 3-trifluoromethyl-4-nitrophenol under aerobic and anaerobic conditions was under 1 week, with 4-amino-3-(trifluoromethyl)phenol observed as the primary degradation product(2). 3-Trifluoromethyl-4-nitrophenol is stable to hydrolysis at pH 5, 7, and 9; however, photolysis may be an important environmental fate process(2). 3-Trifluoromethyl-4-nitrophenol photodegraded in unbuffered distilled water under natural sunlight with a half-life of 3.3 days(2).|AQUATIC FATE: In natural waters that are in contact with bottom sediments, 4-nitro-3-trifluoromethylphenol disappeared within two weeks(1).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3-trifluoromethyl-4-nitrophenol, which has an estimated vapor pressure of 1.3X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), indicates that it is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 3-trifluoromethyl-4-nitrophenol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 21 days(SRC), calculated from its rate constant of 7.7X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 3-Trifluoromethyl-4-nitrophenol undergoes photolysis in aqueous solutions (4), and may be subject to photolysis in the air(SRC).

The rate constant for the vapor-phase reaction of 3-trifluoromethyl-4-nitrophenol with photochemically-produced hydroxyl radicals has been estimated as 7.7X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 21 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 3-Trifluoromethyl-4-nitrophenol is stable to hydrolysis at pH 5, 7, and 9(2). 3-Trifluoromethyl-4-nitrophenol photodegraded in unbuffered distilled water under natural sunlight with a half-life of 3.3 days(2). The principle identified photoproduct was 2,5-dihydroxybenzoic acid. There was no build-up of photoproducts and by the end of the experiment (11 days), most of the degradation products were unextractable(2). 3-Trifluoromethyl-4-nitrophenol irradiated with light at 365 nm, degraded in pH 9 buffered solution with a half-life of 22.4 hours(3). Trifluoroacetic acid was observed as the main degradation product(3). At pH 7, the observed photolysis half-life was 91.7 hours(3).

The amount of 3- trifluoromethyl-4-nitrophenol uptake by fish has been correlated to pH and total hardness of the water(1). Ten times as much 3-trifluoromethyl-4-nitrophenol was found in fish residing in soft-acid water as compared to hard- alkaline water (1). 3-Trifluoromethyl-4-nitrophenol is not readily metabolized by aquatic organisms and is generally excreted in an unaltered form(1). Maximum BCF values of 50.3 for viscera, 1.3 for fillet, and 8.4 for whole body tissues were measured for rainbow trout that were exposed to nonradiolabeled plus uniformly phenyl ring-labeled C-14 3-trifluoromethyl-4-nitrophenol, at a nominal concentration of 62.0 ug/L, under flow-through aquarium conditions at a pH of 7.8(1). According to a classification scheme(2), this BCF data suggests the potential for bioconcentration in aquatic organisms is low(SRC).

128.82 L/kg|A correlation was observed between pH and the soil adsorption properties of 3-trifluoromethyl-4-nitrophenol(1). 3-Trifluoromethyl-4-nitrophenol is a weak acid with pKa of 6.07(2), indicating that it will partially exist as an anion under environmental conditions(SRC). At acidic pH, 3-trifluoromethyl-4-nitrophenol exists primarily as the protonated acid species, but under alkaline conditions it exists predominantly as the conjugate base (anion). Soil adsorption coefficients (Kd) ranging from 1.11 to 11.7 were measured in 4 different soils at pH 6, while Kd values ranging from 0.157 to 2.01 were measured in the same 4 soils at pH 8(1). At pH 6 the Kd values correspond to Koc values of 224 (sandy loam soil 64% sand, 32% silt, 4% clay), 229 (loamy sand 84% sand, 14% silt, 2% clay), 213 (sandy soil 96% sand, 2% silt, 2% clay), 390 (loam soil 44% sand, 46% silt, 10% clay)(1). The Koc values at pH 8 are 38 (sandy loam soil 64% sand, 32% silt, 4% clay), 50 (loamy sand 84% sand, 14% silt, 2% clay), 30 (sandy soil 96% sand, 2% silt, 2% clay), 52 (loam soil 44% sand, 46% silt, 10% clay)(1). According to a classification scheme(3), this range of Koc values indicates that 3-trifluoromethyl-4-nitrophenol is expected to have high to very high mobility under alkaline conditions, and moderate mobility under acidic conditions(SRC).

3-Trifluoromethyl-4-nitrophenol is a weak acid with pKa of 6.07(1), indicating that it will partially exist as its conjugate base (anion) under environmental conditions, and anions do not volatilize(SRC). The Henry's Law constant for the free acid (neutral species) is estimated as 1.9X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(2). This Henry's Law constant indicates that the neutral species of 3-trifluoromethyl-4-nitrophenol is expected to be essentially nonvolatile from moist soil and water surfaces(SRC). Volatilization from dry soil surfaces is not expected(SRC), based upon an estimated vapor pressure of 1.3X10-3 mm Hg determined from a fragment constant method(3).

Occupational exposure to 3-trifluoromethyl-4-nitrophenol may occur through inhalation of dust and dermal contact with this compound at workplaces where it is produced or used. (SRC)

/SIGNS AND SYMPTOMS/ Acute Hazards: Corrosive. Causes irreversible eye damage and skin burns. May be fatal if swallowed. Harmful if absorbed through skin or inhaled. /Sea Lampry Larvicide/|/SIGNS AND SYMPTOMS/ Acute hazards: Corrosive. Causes irreversible eye damage. May be fatal if swallowed. Harmful if absorbed through skin or inhaled. /TFM-BAR/

3-trifluoromethyl-4-nitrophenol

An average of approximately 80,000 pounds of TFM active ingredient was applied in the Great Lakes from 1993 to 1997.

TFM-HP SEA LAMPREY LARVICIDE Active Ingredient 36.5%TFM, 3-Trifluoromethyl-4-nitrophenol, sodium salt (equivalent to 33.0% 3-trifluoromethyl-4-nitrophenol)|TFM-BAR Active Ingredient 23.0% 3-Trifluoromethyl-4-nitrophenol

Analyte: 3-trifluoromethyl-4-nitrophenol; matrix: water; procedure: high-performance liquid chromatography with ultraviolet spectrophotometry at 330 nm|Analyte: 4-nitro-3-trifluoromethylphenol; matrix: food; procedure: Fourier transform nuclear magnetic resonance spectroscopy|Analyte: 3-trifluoromethyl-4-nitrophenol; matrix: edible tissure of fish; procedure: liquid chromatography with ultraviolet-visible detection