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Trifluralin

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Trifluralin Basic information
Trifluralin Chemical Properties
  • Melting point:48.5°C
  • Boiling point:139°C
  • Density 1.294
  • vapor pressure 1.97 at 30 °C (effusion method, DePablo, 1976)
  • Flash point:100 °C
  • storage temp.  APPROX 4°C
  • pka-1.45±0.50(Predicted)
  • form Crystalline Solid
  • color Bright orange
  • Water Solubility <0.01 g/100 mL at 22.5 ºC
  • Merck 13,9757
  • BRN 1893555
  • Henry's Law Constant10.19 and 14.89 in distilled water and 33.3‰ NaCl at 20 °C, respectively (wetted-wall column, Rice et al., 1997a)
  • CAS DataBase Reference1582-09-8(CAS DataBase Reference)
  • NIST Chemistry ReferenceTrifluralin(1582-09-8)
  • IARC3 (Vol. 53) 1991
  • EPA Substance Registry SystemTrifluralin (1582-09-8)
Safety Information
MSDS
Trifluralin Usage And Synthesis
  • DescriptionTrifuralin (sold under trademe such as Treflan, Elancolan or Trefanocide) is a selective pre-emergence herbicide. It is used for pre-plant soil incorporation for the control against annual grasses and some broadleaf annual weeds. It is widely used on soybeans and cotton. It also finds its use in a large number of food crops, including broccoli, cabbage, onions, leafy green vegetables, beans, tomatoes, potatoes, wheat, sugar beet, and sugar cane. For its use on fruit trees, the plant must not be bearing fruit at the time of application. It may also be used to protect residential ornamental plants, such as trees, herbaceous plants, woody shrubs, and vines.
    Trifluralin has low water solubility. It has high affinity for soil and is relatively immobile. It is not acutely toxic mammals, but it is highly toxic to fish and other aquatic organisms.
  • References
    1. https://www.epa.gov
    2. http://www.toxipedia.org
    3. https://pubchem.ncbi.nlm.nih.gov
    4. http://www.who.int
    5. https://aggie-horticulture.tamu.edu
  • DescriptionTrifluralin 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.
  • Chemical PropertiesYellowish-orange solid. Insoluble in water; soluble in xylene, acetone, and ethanol.
  • Chemical PropertiesTrifluralin is an orange crystalline solid.
  • UsesPreemergence herbicide for controlling many grasses and broad-leaved weeds.
  • UsesPre-emergence herbicide used for grass control in crops.
  • UsesTrifluralin 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.
  • DefinitionChEBI: A substituted aniline that is N,N-dipropylaniline substituted by a nitro groups at positions 2 and 6 and a trifluoromethyl group at position 4. It is an agrochemical used as a pre-emergence herbicide.
  • General DescriptionYellow-orange crystalline solid. Denser than water and not soluble in water. Hence sinks in water. Melting point 48.5-49°C. Used as a selective pre emergence herbicide.
  • Reactivity ProfileTrifluralin is a trifluoromethyl dinitroaniline derivative. Dinitroaniline has a record of industrial explosions. Nothing has been reported implicating Trifluralin in any such accidents. This may be because of the trifluoromethyl substitution may mitigate the instability of the molecule. However, care should be taken in the extremes of heat, shock, and friction sources that may trigger an explosive release of energy.
  • Health HazardDust may irritate eyes. No toxic symptoms have been observed during the manufacture and use of Trifluralin.
  • Fire HazardSpecial Hazards of Combustion Products: Toxic and irritating hydrogen fluoride gas may be formed in fires.
  • Agricultural UsesHerbicide: Trifluralin is a selective, pre-emergence herbicide used to control many annual grasses and broadleaf weeds in a large variety of tree fruit, nut, vegetable, and grain crops, including soybeans, sunflowers, cotton, and alfalfa. It is also used on rights-of-way, on set-aside land (i.e., arable land temporarily taken out of use). A general use pesticide (GUP). Not approved for use in EU countries . Registered for use in the U.S.
  • Trade nameAGREFLAN®; AGRIFLAN® 24; ASHLADE TRIMARAN®; AUTUMN KITE®; BROADSTRIKE®; BUCKLE®; CALLIFORT®; CAMPBELL'S TRIFLURON®; CHANDOR®; COMMENCE®; CRISALIN®; DEVRINOL T®; DIGERMIN®; ELANCOLAN®; FLINT®; FLORA®; FLURENE SE®; FLUTRIX®; FREEDOM®; GORDON’S WEEDER®; HERBIFLURIN®; IPERSAN®; JANUS®; L-36352®; LILLY 36,352®; LINNET®; MARKSMAN®; MARKSMAN 2, TRIGARD®; M. T. F®; NITRAN®; OLITREF®; ONSLAUGHT®; PREMERLIN 600 CE®; SINFLOWAN®; SOLO®; SU SEGURO CARPIDOR®; TEAM®; TREFANOCIDE®; TREFICON®; TREFLAN®; TREFLANOCIDE®; TRIFARMON®; TRIFLURALINA® 600; TRIFLUREX®; TRIFUREX®; TRIGARD®; TRIKEPIN®; TRILIN®; TRILIN® 10G; TRIM®; TRIMARAN®; TRIPART TRIFLURALIN 48 EC; TRISTAR®; TRUST®; TURFLAN®; URANUS® (trifluralin + linuron)
  • Safety ProfileModerately toxic by ingestion and intraperitoneal routes. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental carcinogenic and tumorigenic data. Human mutation data reported. When heated to decomposition it emits very toxic fumes of Fand NOx. See also FLUORIDES.
  • Potential ExposureA potential danger to those involved in the manufacture, formulation and application of this selective, preemergence herbicide.
  • Environmental FateBiological. Laanio et al. (1973) incubated 14CF3-tri?uralin with Paecilomyces, Fusar- ium oxysporum, or Aspergillus fumigatus and reported that <1% was converted to 14CO2. From the first-order biotic and abiotic rate constants of tri?uralin in estuarine water and sediment/water systems, the estimated biodegradation half-lives were 2.5–9.7 and 2.4–7.1 days, respectively (Walker et al., 1988).
    Soil. Anaerobic degradation in a Crowley silt loam yielded α,α,α-tri?uoro-N4,N4- dipropyl-5-nitrotoluene-3,4-diamine and α,α,α-tri?uoro-N4,N4-dipropyltoluene-3,4,5-tri- amine (Parr and Smith, 1973). Probst and Tepe (1969) reported that tri?ur
    Golab et al. (1979) studied the degradation of tri?uralin in soil over a 3-year period. They found that the herbicide undergoes N-dealkylation, reduction of nitro substituents, followed by the formation cyclized products. Of the 28 transformation products
    Zayed et al. (1983) studied the degradation of tri?uralin by the microbes Aspergillus carneus, Fusarium oxysporum and Trichoderma viride. Following an inoculation and incubation period of 10 days in the dark at 25°C, the following metabolites were identified: α,α,α-trifluoro-2,6-dinitro-N-propyl-p-toluidine, α,α,α-trifluoro-2,6-dinitro-p-toluidine, 2-amino-6-nitro-α,α,α-tri?uoro-p-toluidine and 2,6-dinitro-4-tri?uoromethyl phenol. The reported half-life in soil is 132 days (Jury et al., 1987).
    The half-lives for tri?uralin in soil incubated in the laboratory under aerobic and anaerobic conditions ranged from 33 to 375 days (Probst et al., 1967; Parr and Smith, 1973; Kearney et al., 1976; Zimdahl and Gwynn, 1977) to 4 to 70 days, respectively (
  • Solubility in organicsFreely soluble in Stoddard solvent (Windholz et al., 1983), chloroform, methanol (Probst et al., 1967), acetone (400 g/L), xylene (580 g/L) (Worthing and Hance, 1991), ether, and ethanol (quoted, Bailey and White, 1965)
  • ShippingUN2588 Pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.
  • Toxicity evaluationTechnical trifluralin has low acute toxicity, whereas solvents often used for the emulsification of trifluralin have been shown to be irritating to the eyes and skin. An active component of trifluralin toxicity is the volatile nitrosamine, N-nitroso-din- propylamine, which may be the active compound in trifluralin toxicity.
  • IncompatibilitiesTrifluralin is a trifluoromethyl dinitroaniline derivative. Dinitroaniline has a record of industrial explosions. Nothing has been reported implicating trifluralin in any such accidents. This may be because of the trifluoromethyl substitution may mitigate the instability of the molecule. However, care should be taken in the extremes of heat, shock, and friction sources that may trigger an explosive release of energy. Fluorocarbons can react violently with barium, potassium, sodium.
  • Waste DisposalDissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed. Trifluralin does contain fluorine, and therefore incineration presents the increased hazard of HF in the off-gases. Prior to incineration, fluorine-containing compounds should be mixed with slaked lime plus vermiculite, sodium carbonate or sand-soda ash mixture (90-10).
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