Trifluralin

log Kow = 5.34

5.3

1.294 at 77 °F (USCG, 1999) - Denser than water; will sink

1.36 at 22 °C

Density (at 22 °C): 1.36 g/cm³

1.36 @ 22°C

Yellow crystals

YELLOW-ORANGE PRISMS

Orange crystalline solid

less than 0.1 mg/mL at 72.5 °F (NTP, 1992)

In acetone, chloroform, acetonitrile, toluene, ethyl acetate >1000, methanol 33-40, hexane 50-67, all in g/L at 25 °C

Solubility at 25 °C: 82 g/100 mL dimethylformamide; 83 g/100 mL dioxane; 44 g/100 mL methyl cellosolve; 88 g/100 mL methyl ethyl ketone

Slightly soluble in water (0.0024 g/100 mL)

In water (25 °C), 18.4 mg/L at pH = 5, 0.221 mg/L at pH 7, 0.189 mg/L at pH 9

Solubility in water, mg/l at 20 °C: 0.2 (very poor)

greater than 185 °F (NTP, 1992)

Flash Point > 185 °F

151 °C (closed cup); 153 °C (tech, open cup)

100 °C c.c.

Decomposes (NTP, 1992)

BP: 139-140 °C at 4.2 mm Hg

at 0.5kPa: 139-140 °C

When heated to decomposition it emits toxic fumes of /hydrogen fluoride and nitrogen oxides/.

Susceptible to decomposition by ultraviolet radiation.

202 °C

115 to 117 °F (NTP, 1992)

42 °C

MP: 48.5-49 °C (technical >95%)

49 °C

49 °C

0.000199 mmHg at 85.1 °F (NTP, 1992)

0.0000458 [mmHg]

4.58X10-5 mm Hg at 25 °C

Vapor pressure, Pa at 25 °C: 0.01

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]；H351: Suspected of causing cancer [Warning Carcinogenicity]；H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]；H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P203, P261, P272, P273, P280, P302+P352, P318, P321, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Danger

Hazard Traits - Bioaccumulation; Carcinogenicity; Environmental Persistence; Environmental tox; Hepatotoxicity and Digestive System Toxicity；Authoritative List - CA TACs; Canada PBiTs; CWA 303(d); OSPAR Priority Action Part A; US EPA NWMP PBTs; US EPA TRI PBTs；Report - if used as a fragrance or flavor ingredient

Commission Regulation (EC) No 451/2000

2010/355/EU

Trifluralin: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Special Hazards of Combustion Products: Toxic and irritating hydrogen fluoride gas may be formed in fires. (USCG, 1999)

Combustible under specific conditions. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.

Trifluralin is used as a herbicide. No information is available on the acute (short-term), chronic (long- term), reproductive, developmental, or carcinogenic effects of trifluralin in humans. Decreased weight gain and effects on the blood and liver were observed in dogs chronically exposed to trifluralin in their diet. Skeletal abnormalities and depressed fetal weight were observed in the offspring of rodents exposed via gavage (experimentally placing the chemical in the stomach). Increased incidences of urinary tract tumors and thyroid tumors were observed in rats exposed to trifluralin in their diet. Trifluralin did not produce statistically significant increases in tumors in other studies. EPA has classified trifluralin as a Group C, possible human carcinogen (cancer-causing agent).

An eye irritant; May cause skin sensitization; [ICSC] Does not uncouple oxidative phosphorylation or induce methemoglobinemia; [EPA Pesticides, p. 120] An eye irritant; May cause skin sensitization; In high-dose animal studies, causes injury to the liver, kidneys, bladder, thyroid, blood, and CNS; [MSDSonline]

NTP; Bioassay of Trifluralin for Possible Carcinogenicity CAS No. 1582-09-8 Report # 034 (1978). NIH Pub # 78-834.

USEPA; Health Advisories for 50 Psticides (Including Trifluralin) (1988) PB88-245931. Documents summarize health effects of 50 pesticides including trifluralin. Topics discussed include: General effects and properties; Pharmacokinetics; Health effects in humans and animals; Quantification of toxicological effects; Other criteria and standards, Analytical methods and treatment technologies.

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Trifluralin, EPA 738-R-95-040 (April 1996). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of January 31, 2012: http://www.epa.gov/pesticides/reregistration/status.htm]

USEPA/OPPTS; Report of the Food Quality Protection Act (FQPA) Tolerance Reassessment Progress and Risk Management Decision (TRED) for Trifluralin (August 31, 2004)[Available from, as of August 27, 2012: http://www.epa.gov/pesticides/reregistration/status.htm]

Tolerances are established for residues of the herbicide and plant growth regulator trifluralin, alpha,alpha,alpha-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine, in or on the following raw agricultural commodities: [Table#2670]

Based on the reviews of the generic data for the active ingredients trifluralin, the Agency has sufficient information on the health effects of trifluralin and on its potential for causing adverse effects in fish and wildlife and the environment. Therefore, the Agency concludes that products containing trifluralin are eligible for reregistration for all registered uses except for nongrass forage/fodder/straw/hay and dill provided the labeling changes and other requirements specified in this document are implemented. The Agency has determined that trifluralin products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Trifluralin is found on List A, which contains most pesticides that are used on foods and, hence, have a high potential for human exposure. List A consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0179; Pesticide type: Herbicide (growth regulator); Registration Standard Date: 04/01/87; Case Status: RED Approved 09/95; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Trifluralin; Data Call-in (DCI) Date(s): 03/03/95, 04/30/96; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.

Fire Extinguishing Agents: Water, foam, dry chemical, carbon dioxide (USCG, 1999)

Use water spray, foam, powder, carbon dioxide.

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth.

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.；SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.；INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.；INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital.；OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

Will emit toxic fumes as it burns. Wear full protective clothing and use self-contained breathing apparatus. Nonessential personnel should be restricted from area of intense smoke. Do not allow water run-off from fire site to enter nearby streams, ponds or lakes. Keep containers cooled with water spray. /Gowan Trifluralin 10G/

... Use dry chemical, carbon dioxide, water spray, or alcohol foam extinguishers. ...

Do not store near heat or open flame. /Gowan Trifluralin 10G/

Do not contaminate water, food or feed by storage or disposal. ... Store in original bag only. /Gowan Trifluralin 10G/

This product is stable under normal storage conditions for a minimum of 3 yr when stored in adequate packing in metal containers with polyethylene lining, at room temp. The biological activity of digermin remains practically unvaried for 2 yr under environmental conditions, provided the product is stored in its unopened & undamaged original containers, & in shaded & possibly well-aired places. Avoid freezing. Store above 40 °F. Do not store near heat or flame.

Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water. /Residential users/

Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR Part 170. /Gowan Trifluralin 10G/

... Remove all ignition sources. Dampen spilled material with alcohol to avoid dust, then transfer material to a suitable container. Use absorbent dampened with alcohol to pick up remaining material. Wash surfaces well with soap and water. Collect waste material in the most convenient and safe manner and deposit in sealed containers. Ventilate area after clean-up is complete. ...

Do not wash away into sewer. Sweep spilled substance into sealable containers; if appropriate, moisten first to prevent dusting. Carefully collect remainder, then remove to safe place. Personal protection: P2 filter respirator for harmful particles.

If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label./Residential users/

After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash. /Residential users/

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.；STORAGE PRECAUTIONS: You should protect this material from exposure to light, and store it in under ambient temperatures. (NTP, 1992)

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Trifluralin is resistant to oxidation, and acid and alkaline hydrolysis. The major environ effect of concern in the disposal of trifluralin is its toxicity to fish. Trifluralin is known to be strongly adsorbed onto the soil and is resistant to movement by water, and burial in specially designated landfills or isolated areas away from water supplies is the procedure recommended for the disposal of small quantities of trifluralin. For the decontamination of trifluralin containers, the National Agricultural Chemical Association triple rinse and drain procedure is recommended. Rinse soln from containers can be poured into the spray tank for application. Trifluralin bags should be destroyed when empty and disposed of through regular refuse collection system or buried in an isolated area away from water supplies. Recommendable method: Landfill. Not recommendable methods: Discharge to sewer, & thermal destruction.

Wastes resulting from the use of this product may be disposed of on site or at an approved waste disposal facility. /Gowan Trifluralin 10G/

For more Disposal Methods (Complete) data for TRIFLURALIN (6 total), please visit the HSDB record page.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR Part 170. /Gowan Trifluralin 10G/

For terrestrial uses, do not apply directly to water, or to areas where surface water is present or to intertidal areas below the mean high water mark. Drift or runoff from treatment areas may be hazardous to aquatic organisms in neighboring aquatic sites. /Gowan Trifluralin 10G/

Users should: Wash hands before eating, drinking, chewing gum, using tobacco or using the toilet. Remove clothing immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing. /Gowan Trifluralin 10G/

Do not apply this product in a way that will contact workers or other persons, either directly or through drift. Only protected handlers may be in the area during application. /Gowan Trifluralin 10G/

For more Preventive Measures (Complete) data for TRIFLURALIN (15 total), please visit the HSDB record page.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:；IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.；SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.；FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

Mice were fed trifluralin at 1000, 1500 & 2000 ppm in diet for 12 or 14 weeks. Tumors were induced by admin 8 mg of benzo(a)pyrene orally at two time periods. Inhibition of tumorigenesis in lung & forestomach by trifluralin was observed when it was fed in diet 1 wk before or 1 day following exposure to benzo(a)pyrene.

LC50; Species: Colinus virginianus (Northern Bobwhite Quail) age 12 days; dietary >5000 ppm for 8 days

LD50; Species: Colinus virginianus (Northern Bobwhite Quail) age 16 weeks; oral via capsule >2000 mg/kg

LC50; Species: Anas platyrhynchos (Mallard Duck) age 14 days; dietary >5000 ppm for 8 days

LD50; Species: Anas platyrhynchos (Mallard Duck) age 3-4 months; oral via capsule >2000 mg/kg bw

For more Ecotoxicity Values (Complete) data for TRIFLURALIN (99 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), experimental Koc values ranging from 397 to 27,900(2-8), indicate that trifluralin is expected to have moderate to no mobility in soil(SRC). Volatilization of trifluralin from moist soil surfaces may be an important fate process(SRC) given a Henry's Law constant of 1.03X10-4 atm-cu m/mole(9). Trifluralin is shown to volatilize from both moist and dry soils to the atmosphere(10-12), although the volatilization rate is greater for moist soils(13). Trifluralin was volatilized 16%, 28% and 40% in dry, moist and flooded soils over a 32 day incubation period(10). Sunlight photolysis of trifluralin adsorbed to soil TLC plate resulted in 18.4% removal in 7 days(14) although in the field, direct photolysis on soil surfaces does not appear to compete with volatilization(13,15). Trifluralin biodegrades faster in anaerobic soils than in aerobic soils(16). Trifluralin degraded with half-lives of 189, 202, and 116 days in sandy loam, clay loam, and loam soils, respectively, when incubated aerobically in the dark at 22 °C for 364 days(17). Trifluralin degraded with half-lives of 22-59 days in sandy loam, loam, and clay loam soils incubated anaerobically in the dark at 22 °C for 60 days following an aerobic incubation period of 30 days(17).

TERRESTRIAL FATE: Trifluralin respiration rates were measured in 16 surface soils (top 15 cm) using a sealed chamber method and headspace analysis(1).；Table: Site Characteristics & Respiration Rates [Table#2669]

FIELD STUDY: Potato fields were grown under natural conditions (untreated), amended with sewage sludge or amended with yard waste compost(1). Trifluralin was applied at 0.75 lb/acre and incorporated into the soil as a preemergent and the fields were planted. Trifluralin residues were highest in sludge treated soil and lowest in untreated soil, this was attributed to the higher pH and concentration of Ca and Cu in the sludge treated soil(1).

AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 397 to 27,900(2-8) indicate trifluralin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(9) based upon a Henry's Law constant of 1.03X10-4 atm-cu m/mole(10). Using this Henry's Law constant and an estimation method(9), volatilization half-lives for a model river and model lake are 21 hours and 12 days, respectively(SRC). The volatilization from a model pond is about 30 months when adsorption is considered(11). According to a classification scheme(12), measured BCF of 1289 to 9586(13-16), suggest bioconcentration in aquatic organisms is very high(SRC). Trifluralin is stable to hydrolysis(17). The experimental half-life for the direct photolysis of trifluralin in near surface water, latitude 40 deg N in the summer is 22 min(18). Biodegradation of trifluralin is not important based on the rapid photodegradation(18).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trifluralin, which has a vapor pressure of 4.58X10-5 mm Hg(2) at 25 °C, will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase trifluralin 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 16 hours(SRC), calculated from its rate constant of 2.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase trifluralin may be removed from the air by wet and dry deposition(SRC). Trifluralin contains chromophores that absorb at wavelengths >290 nm(4) and the observed half-life for trifluralin in July sunlight ranged from 19-74 min(5). In the presence of ozone, the rate of this reaction increases(6-7).

Trifluralin was qualitatively detected in domestic and imported agricultural commodities in the FDA's pesticide residue monitoring program, FY 83-86(1). The FDA found residues of trifluralin in 3 of 6391 domestic agricultural commodity samples and 1 of 12,044 imported samples at concentrations ranging from 0.10 to 1.0 ppm and 1.0 ppm, respectively, survey was done 1981 to 1986(2-3). For 1988, trifluralin was found in 4 of 13,980 samples but it was not detected in 13,085 samples from 1989(4).

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.；Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

Trifluralin was not detected (detection limit 0.1 ug/kg) in 100 raw milk, 30 full-fat milk, 20 half-skimmed milk and 20 skimmed milk samples(1). Raw milk was provided by a local farm and all other milk samples were obtained from local supermarkets in Shenyang, China(1).

/BIRDS and MAMMALS/ Application of trifluralin to fertile mallard eggs, by immersing them for 30 sec in an aqueous solution, resulted in embryonic death at exposure levels calculated to be 0.8 times that expected after usual application in the field, i.e., 1.6 lb/acre (1.8 kg/ha). Exposure at this level also reduced growth and increased the rate of bill malformation and of stuntedness in the embryos.

/BIRDS and MAMMALS/ Oral toxicity /female mallard ducks and male pheasants 3-4 months of age/, LD50 >2000 mg/kg, acute symptoms: very mild ataxia only.

/AQUATIC SPECIES/ ... In the present study, /the authors/ investigated the acute effects of five agricultural pesticides on juvenile coho salmon (Oncorhynchus kisutch) olfaction using the electro-olfactogram (EOG), a measure of odorant-evoked field potentials. Electro-olfactogram responses to the odorant L-serine were measured during and following a 30-min exposure of the left olfactory rosette to chlorothalonil, endosulfan, glyphosate acid, iodocarb (IPBC), trifluralin, and 2,4-dichlorophenoxyacetic acid. With the relatively insoluble pesticides endosulfan and trifluralin, decreases in EOG amplitude were only apparent at relatively high concentrations (100 and 300 ug/L, respectively) following 20 min of exposure and were absent for chlorothalonil (1 mg/L). With the water-soluble herbicide glyphosate, significant EOG reductions occurred within 10 min of exposure to 1 mg/L and more rapidly with higher concentrations. Recovery of EOG post-glyphosate exposure was concentration-dependent, and complete recovery was not observed with some concentrations at 60 min postexposure. Dichlorophenoxyacetic acid only affected EOG at high concentration (100 mg/L), where it eliminated EOG within 2 min of exposure. With IPBC, EOG was decreased at 25 min of exposure to 1 ug/L; higher concentrations caused decreases to occur more rapidly. Excluding IPBC and glyphosate, all EOG reductions occurred at concentrations greater than the current Canadian water-quality guidelines and reported 96-hr lethality values. ...Results show that olfactory neurons can be impaired rapidly by some current-use pesticides, even at exposures in the low-ug/L range.

/AQUATIC SPECIES/ Occurrence of vertebral dysplasia in brown trout salmo trutta was attributed to preemergence herbicide, active ingredient trifluralin, which was accidentally discharged into stream.

For more Ecotoxicity Excerpts (Complete) data for TRIFLURALIN (6 total), please visit the HSDB record page.

Hazard Traits - Bioaccumulation; Carcinogenicity; Environmental Persistence; Environmental tox; Hepatotoxicity and Digestive System Toxicity；Authoritative List - CA TACs; Canada PBiTs; CWA 303(d); OSPAR Priority Action Part A; US EPA NWMP PBTs; US EPA TRI PBTs；Report - if used as a fragrance or flavor ingredient

Commission Regulation (EC) No 451/2000

2010/355/EU

Trifluralin: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Tolerances are established for residues of the herbicide and plant growth regulator trifluralin, alpha,alpha,alpha-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine, in or on the following raw agricultural commodities: [Table#2670]

Based on the reviews of the generic data for the active ingredients trifluralin, the Agency has sufficient information on the health effects of trifluralin and on its potential for causing adverse effects in fish and wildlife and the environment. Therefore, the Agency concludes that products containing trifluralin are eligible for reregistration for all registered uses except for nongrass forage/fodder/straw/hay and dill provided the labeling changes and other requirements specified in this document are implemented. The Agency has determined that trifluralin products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Trifluralin is found on List A, which contains most pesticides that are used on foods and, hence, have a high potential for human exposure. List A consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0179; Pesticide type: Herbicide (growth regulator); Registration Standard Date: 04/01/87; Case Status: RED Approved 09/95; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Trifluralin; Data Call-in (DCI) Date(s): 03/03/95, 04/30/96; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Trifluralin is included on this list.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b).

(AZ) ARIZONA 2 ug/l

(FL) FLORIDA 4.5 ug/L

(ME) MAINE 45 ug/l

(WI) WISCONSIN 7.5 ug/l

Four monkeys (2 males and 2 females) were administered 2 mg/kg radio-labeled ethalfluralin in ethanol intravenously or topically to the forearm and the plasma level determined for 120 hours to determine an area under the curve for both types of applications. Two compartments were noted with one-half lives of 1.71 hours for the plasma distributive phase and 79.1 hours for the terminal plasma disappearance phase. ... /Ethalfluralin/

Salmon parr salmo salar were subjected to high initial concentrations of trifluralin & then maintained in clear water for 12 months. Some were removed at preselected intervals for exam by x-ray and chemical analysis. Half-life of trifluralin in salmon parr was 40.5 days.

Extensive nitro-reduction to the corresponding amines occurred, probably as a result of metabolism by the gut microflora. Absorbed trifluralin was extensively metabolized, primarily by N-dealkylation and nitro-reduction, and then excreted in the urine.

In a rat metabolism study, (14)C-trifluralin ( >98% radiochemical purity) in corn oil was administered by gavage at 300 mg/kg/day to 5 Fischer 344 rats/sex on three consecutive days. Metabolite characterization of the 24-48 hour urinary samples (pooled by sex) and quantitation of urinary samples collected at 0-24, 24-48, and 48-54 hours and pooled by sex were performed using liquid scintillation counting, silica gel column chromatography, TLC, HPLC, NMR, and mass spectroscopy. The objective of this study was to identify the urinary metabolites of trifluralin. There was no sex-dependent effect on metabolic profiles. A minimum of 20-30 non-conjugated metabolites and an additional 10-20 conjugated metabolites were present in the urine, but no parent compound was detected. Information on the percentage of the administered dose excreted in the urine was not provided. However, no single metabolite accounted for more than 8-10% of the total urinary radioactivity, and the majority of the metabolites were present at 1-2% of the total urinary radioactivity. Thus, almost all of the metabolites were minor (<5% of the total radioactive dose). Metabolite F1B was found at 8.2-8.9% of the total urinary radioactivity in both sexes, and Metabolite F2, N-((3-(acetylamino)-2-amino-5-(trifluoromethyl)) phenyl)acetamide, was found at 4.0-5.2%. Metabolite F1B was partially characterized as retaining the trifluoromethyl groups, the two equivalent aromatic protons, and the two nitro groups, but the propyl groups were lost. Ten other metabolites were identified (<0.1-3.7% of total urinary radioactivity, each compound in each sex). Two additional metabolites were partially characterized (0.1-2.6% of total urinary radioactivity, each compound in each sex). Four metabolic pathways were identified as follows: (i) oxidative N-dealkylation of one or both propyl groups and metabolites which were hydroxylated on the propyl side chain; (ii) reduction of one or both nitro groups to the corresponding a

Major metabolites /found in urine & feces of treated ruminants/ were unidentified polar compounds, but N',N'-dipropyl-3-nitro-5-trifluoromethyl-ortho-phenylenediamine & N(4)N(4)-dipropyl-alpha,alpha,alpha-trifluorotoluene-3,4,5-triamine were also formed.

Trifluralin is dealkylated in rumen /of dairy animals/, losing 1 or both propyl groups; nitro groups are reduced to 1 or 2 amino groups. 2 types of reactions occur simultaneously, leading to a trifluoromethyltriaminobenzene.

For more Metabolism/Metabolites (Complete) data for TRIFLURALIN (6 total), please visit the HSDB record page.

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.

Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES.

... Rats dosed orally with radiolabelled trifluralin (14)C-CF3 or (14)C-N-propyl-; 100 mg/kg bw) excreted 80% of the dose in the feces; only 8% was unchanged trifluralin. Incomplete absorption was indicated by the finding that only 11-14% of the radioactivity was recovered from bile. ...

Four monkeys (2 males and 2 females) were administered 2 mg/kg radio-labeled ethalfluralin in ethanol intravenously or topically to the forearm and the plasma level determined for 120 hours to determine an area under the curve for both types of applications. ... After 120 hours label was not detectable in 2 (1 male and 1 female) of the 4 animals studied. Since the 2 animals with undetectable plasma levels at 120 hour yielded the most consistent data, data from these animals were used to calculate the AUCs. The dermal absorption was determined by ratio of the area under the plasma curve AUC; [(AUC-dermal/(AUC-i.v.)] x 100 = 2.84%. /Ethalfluralin/

Approx 80% of ingested compound was excreted in feces, remainder in urine /of rats & dogs studied/.

Trifluralin is a herbicide used to control annual grasses and some broadleaf annual weeds on a variety of crops, shrubs, and flowers. It is used mostly on cotton, as well as on soybeans and some fruits and vegetables.

Pre-emergence herbicide used to control grass; [Merck Index] Use as a herbicide, especially in cotton production; [Hawley]

Farming (Pesticides) [Category: Industry]

For trifluralin (USEPA/OPP Pesticide Code: 036101) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Herbicide

Trifluralin is a selective soil herbicide which acts by entering the seedling in the hypocotyls region and disrupting cell division. It also inhibits root development.

SELECTIVE HERBICIDE FOR GRASSES & BROADLEAF WEEDS, OF WHICH 52% IS USED ON SOYBEANS, 40% ON COTTON, 8% ON OTHER FIELD CROPS, VEGETABLES, FRUIT, NUTS, NURSERY CROPS, ALFALFA, PASTURE LAND, & SUMMER FALLOW, & 2% AS SELECTIVE HERBICIDE IN OTHER APPLICATIONS (1972)

(1975) 9.86X10+9 GRAMS (CONSUMPTION)

Trifluralin is produced by nitration of 4-chloro-trifluorotoluene, followed by treatment with dipropylamine.

It is prepared by reacting di-n-propylamine with 2,6-dinitro-4-trifluoromethylchlorobenzene.

REACTION OF 4-TRIFLUORO-2,6-DINITROCHLOROBENZENE AND DIPROPYLAMINE IN THE PRESENCE OF SODIUM CARBONATE

In the USA, trifluralin is available as 94.5-98% active ingredient technical product. It is available as emulsifiable concentrates, granules and liquid formulations. In Europe, a soluble concentrate is also available. In the USSR, trifluralin is available as emulsifiable concentrates and in granules.

Sorne examples of trade names are: Agreflan; Agriflan 24; Elancolan; L 36352; Lily 36,352; Nitran; Nitran K; Olitref; Super-Treflan; Synfloran; Trefanocide; Treflan; Trifloran; Trifluraline; Trikepin; Tristar.

USEPA/OPP Pesticide Code 036101; Trade Names: Treflan.

Emulsifiable concentrate, granular, liquid, wettable powder.

For more Formulations/Preparations (Complete) data for TRIFLURALIN (114 total), please visit the HSDB record page.

Environmental transformation -> Pesticides (parent, predecessor)

HERBICIDES