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Trifluralin
Benzenamine, 2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)- · Tristar · Trifluraline · Digermin · Trifiuralin · A,A,A-TRIFLUORO-2,6-DINITRO-N,N-DIPROPYL-P-TOLUIDINE · Tri-4 · L36352
Identifikatoren & physikalische Daten
| CAS No. | 1582-09-8 |
|---|---|
| Summenformel | C13H16F3N3O4 |
| Durchschnittliche Molmasse | 335,28 g/mol |
| Monoisotopische Masse | 335,10929049 g/mol |
| SMILES | CCCN(CCC)c1c([N+](=O)[O-])cc(C(F)(F)F)cc1[N+](=O)[O-] |
| InChIKey | ZSDSQXJSNMTJDA-UHFFFAOYSA-N |
| PubChem CID | 5569 |
| ChEMBL | CHEMBL31970 |
| ChEBI | CHEBI:35027 |
| EC No. | 216-428-8 |
| DTXSID | DTXSID4021395 |
| Lokaler Name | Trifluralin |
Chemische & physikalische Eigenschaften
| XLogP | 5,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 94,9 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 8 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 23 |
| Formalladung | 0 |
| Komplexität | 392 |
| LogP (Verteilungskoeffizient) | log Kow = 5.34 |
| Geruch | No appreciable odor |
| Dichte | 1.294 at 77 °F (USCG, 1999) - Denser than waterwill sink1.36 at 22 °CDensity (at 22 °C): 1.36 g/cm³1.36 @ 22°C |
| Color/Form | Yellow crystalsYELLOW-ORANGE PRISMSOrange crystalline solid |
| Löslichkeit | 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 °CSolubility at 25 °C: 82 g/100 mL dimethylformamide83 g/100 mL dioxane44 g/100 mL methyl cellosolve88 g/100 mL methyl ethyl ketoneSlightly 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 9Solubility in water, mg/l at 20 °C: 0.2 (very poor)DMSO : ≥ 100 mg/mL (298.26 mM)Water : < 0.1 mg/mL (insoluble)<0.01 g/100 mL at 22.5 ºC |
| Corrosivity | Technical not corrosive |
| Flammpunkt | greater than 185 °F (NTP, 1992)Flash Point > 185 °F151 °C (closed cup)153 °C (tech, open cup)100 °C c.c. |
| Siedepunkt | Decomposes (NTP, 1992)BP: 139-140 °C at 4.2 mm Hgat 0.5kPa: 139-140 °C139°C |
| Decomposition | When heated to decomposition it emits toxic fumes of /hydrogen fluoride and nitrogen oxides/.Susceptible to decomposition by ultraviolet radiation.202 °C |
| Schmelzpunkt | 115 to 117 °F (NTP, 1992)42 °CMP: 48.5-49 °C (technical >95%)48.5°C |
| Dampfdruck | 0.000199 mmHg at 85.1 °F (NTP, 1992)0.0000458 [mmHg]4.58X10-5 mm Hg at 25 °CVapor pressure, Pa at 25 °C: 0.011.97 at 30 °C (effusion method, DePablo, 1976) |
| Henry-Konstante | Henry's Law constant = 1.03X10-4 atm-cu m/mol at 20 °C10.19 and 14.89 in distilled water and 33.3‰ NaCl at 20 °C, respectively (wetted-wall column, Rice et al., 1997a) |
| Lagerbedingungen | APPROX 4°C |
| pKa (Säurekonstante) | -1.45±0.50(Predicted) |
| Aggregatzustand | Crystalline Solid |
| Farbe | Bright orange |
| Merck | 13,9757 |
| BRN | 1893555 |
| Hauptanwendungen | agricultureenvironmental |
| InChI | 1S/C13H16F3N3O4/c1-3-5-17(6-4-2)12-10(18(20)21)7-9(13(14,15)16)8-11(12)19(22)23/h7-8H,3-6H2,1-2H3 |
| InChIKey | ZSDSQXJSNMTJDA-UHFFFAOYSA-N |
| SMILES | CCCN(CCC)c1c(cc(cc1[N+]([O-])=O)C(F)(F)F)[N+]([O-])=O |
| LogP (Verteilungskoeffizient) | 5.340 |
| CAS Datenbank | 1582-09-8(CAS DataBase Reference) |
| NIST chemische Informationen | Trifluralin(1582-09-8) |
| EPA chemische Informationen | Trifluralin (1582-09-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH317: 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 |
|---|---|
| Regulatorische Informationen | Hazard Traits - BioaccumulationCarcinogenicityEnvironmental PersistenceEnvironmental toxHepatotoxicity and Digestive System ToxicityAuthoritative List - CA TACsCanada PBiTsCWA 303(d)OSPAR Priority Action Part AUS EPA NWMP PBTsUS EPA TRI PBTsReport - if used as a fragrance or flavor ingredientCommission Regulation (EC) No 451/20002010/355/EUTrifluralin: Does not have an individual approval but may be used under an appropriate group standardThe 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.) |
| Weitere Sicherheitsinformationen | IMAP assessments - Benzenamine, 2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)-: Environment tier I assessmentIMAP assessments - Benzenamine, 2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)-: Human health tier I assessment |
| DOT-Kennzeichnung | Class 9 |
| Brandgefahren | 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. |
| Brandpotenzial | This chemical is a combustible solid. ... |
| Gesundheitsgefahren | Dust may irritate eyes. No toxic symptoms have been observed during the manufacture and use of this compound. (USCG, 1999) |
| Gefahrenübersicht | 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 irritantMay cause skin sensitization[ICSC] Does not uncouple oxidative phosphorylation or induce methemoglobinemia[EPA Pesticides, p. 120] An eye irritantIn high-dose animal studies, causes injury to the liver, kidneys, bladder, thyroid, blood, and CNS[MSDSonline] |
| Reaktive Gruppe | Nitro, Nitroso, Nitrate, and Nitrite Compounds, OrganicFluorinated Organic CompoundsAmines, Aromatic |
| EG-Einstufung | Symbol: Xi, NR: 36-43-50/53S: (2)-24-37-60-61 |
| UN-Einstufung | UN Hazard Class: 9UN Pack Group: III |
| Special Reports | NTPBioassay of Trifluralin for Possible Carcinogenicity CAS No. 1582-09-8 Report # 034 (1978). NIH Pub # 78-834.USEPAHealth Advisories for 50 Psticides (Including Trifluralin) (1988) PB88-245931. Documents summarize health effects of 50 pesticides including trifluralin. Topics discussed include: General effects and propertiesPharmacokineticsHealth effects in humans and animalsQuantification of toxicological effectsOther criteria and standards, Analytical methods and treatment technologies.USEPA/Office of Pesticide ProgramsReregistration 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/OPPTSReport 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] |
| FIFRA-Anforderungen | 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: 0179Pesticide type: Herbicide (growth regulator)Registration Standard Date: 04/01/87Case Status: RED Approved 09/95OPP 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): TrifluralinData Call-in (DCI) Date(s): 03/03/95, 04/30/96AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI. |
| Brandbekämpfung | Fire Extinguishing Agents: Water, foam, dry chemical, carbon dioxide (USCG, 1999)Use water spray, foam, powder, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | 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. |
| Erste Hilfe | 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 areatake 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 usedif 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) |
| Sichere Lagerung | Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Store only in original packaging. Store in an area without drain or sewer access. |
| Brandbekämpfungsverfahren | 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. ... |
| Lagerbedingungen | 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/ |
| Reinigungsverfahren | 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 containersif 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/ |
| Freisetung ohne Brand | 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) |
| Entsorgungsverfahren | 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 qualitypotential migration in soil or watereffects on animal and plant lifeand 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. |
| Verschüttetes entsorgen | 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. |
| Preventive Measures | 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. |
| Isolation and Evacuation | 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 directionsalso, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024) |
| Körperbelastung | Trifluralin was detected in maternal serum samples at 0.007 to 8.50 ng/g and in corresponding cord serum at 0.007 to 4.42 ng/g(1). |
| Cancer Sites | EndocrineUrinary |
| Wechselwirkungen | 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. |
| Zielorgane | HematologicHepatic |
| Ökotoxizitätswerte | LC50Species: Colinus virginianus (Northern Bobwhite Quail) age 12 daysdietary >5000 ppm for 8 daysLD50Species: Colinus virginianus (Northern Bobwhite Quail) age 16 weeksoral via capsule >2000 mg/kgSpecies: Anas platyrhynchos (Mallard Duck) age 14 daysSpecies: Anas platyrhynchos (Mallard Duck) age 3-4 monthsoral via capsule >2000 mg/kg bwFor more Ecotoxicity Values (Complete) data for TRIFLURALIN (99 total), please visit the HSDB record page. |
| Umweltverhalten | 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). |
| Lebensmitteluntersuchungswerte | 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). |
| Unerwünschte Wirkungen | 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. |
| Expositionspfade | The substance can be absorbed into the body by inhalation. |
| Milk Concentrations | 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). |
| Ökotoxizitätsauszüge | /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/Lhigher 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. |
| Signs and Symptoms | Redness. Pain. |
| Luftstandards | 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. |
| CERCLA-Meldepflichtmengen | 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). |
| Landesrichtlinien für Trinkwasser | (AZ) ARIZONA 2 ug/l(FL) FLORIDA 4.5 ug/L(ME) MAINE 45 ug/l(WI) WISCONSIN 7.5 ug/l |
| Bundesrichtlinien für Trinkwasser | EPA 10 ug/L |
| Wassergefährdungsklasse (WGK) | 2 |
| UN-Transportnummer | UN 2588 |
| Zollcode | 29214300 |
| RTECS-Nr. | XU9275000 |
| R-Sätze (R) | 36-43-50/53-20/21/22-11-40 |
| Toxizität | LD50 orally in rats: 500 mg/kg (Goldenthal) |
| Gefahrensymbole | XiN,N,Xi,Xn,F |
| Sicherheitshinweise (S) | 2-24-37-60-61-36-26-16-46-36/37 |
| Gefahrenklasse | 9Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Carc. 2Skin Sens. 1 |
| Verpackungsgruppe | III |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 1582-09-8(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Trifluralin is a dinitroaniline herbicide that is approved for preemergence use to control broadleaf weeds in a variety of crops and plants. First approved nearly 50 years ago, trifluralin is a common commercially available herbicide which is used extensively in the United States and other countries. In the early 2000s, trifluralin was banned in Europe following reports of persistence in soil and groundwater leading to concerns of increased risk for toxicity. In general, trifluralin is viewed as a safe herbicide when used according to the instructions. Minimal to no toxicity has been reported in humans following either oral, dermal, or inhalation exposure. There is some evidence that once trifluralin enters the soil and groundwater, it undergoes a complex and extensive series of metabolic steps and can exist as multiple intermediaries depending on the extent of the degradation. This has led to findings that trifluralin may have elevated toxicity in certain aquatic wildlife as particular species of fish and tadpoles have displayed biomarkers of trifluralin toxicity following exposure. Larger vertebrates such as canines have also demonstrated toxicological profiles suggesting an elevated toxicity compared to humans.
Verwenden
Trifluralin is a herbicide, first approved in 1963, for control of annual grasses and broadleaf weeds on a variety of crops. Trifluralin is registered for nonfood uses including residential use. Trifluralin comes in a variety of formulations and is applied as a soil-incorporated treatment.