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| | 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) | | Fp | 100 °C | | storage temp. | APPROX 4°C
| | solubility | DMSO : ≥ 100 mg/mL (298.26 mM);Water : < 0.1 mg/mL (insoluble) | | form | Crystalline Solid | | pka | -1.45±0.50(Predicted) | | color | Bright orange | | Water Solubility | <0.01 g/100 mL at 22.5 ºC | | Merck | 13,9757 | | BRN | 1893555 | | Henry's Law Constant | 10.19 and 14.89 in distilled water and 33.3‰ NaCl at 20 °C, respectively (wetted-wall column,
Rice et al., 1997a) | | LogP | 5.340 | | CAS DataBase Reference | 1582-09-8(CAS DataBase Reference) | | IARC | 3 (Vol. 53) 1991 | | NIST Chemistry Reference | Trifluralin(1582-09-8) | | EPA Substance Registry System | Trifluralin (1582-09-8) |
| | Trifluralin Usage And Synthesis |
| Description | Trifuralin (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 |
- https://www.epa.gov
- http://www.toxipedia.org
- https://pubchem.ncbi.nlm.nih.gov
- http://www.who.int
- https://aggie-horticulture.tamu.edu
| | Description | 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. | | Chemical Properties | Yellowish-orange solid. Insoluble in water; soluble
in xylene, acetone, and ethanol. | | Chemical Properties | Trifluralin is an orange crystalline solid. | | Uses | Preemergence herbicide for controlling many grasses and broad-leaved weeds. | | Uses | Pre-emergence herbicide used for grass control in crops. | | Uses | 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. | | Definition | ChEBI: 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 Description | Yellow-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 Profile | Trifluralin 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 Hazard | Dust may irritate eyes. No toxic symptoms have been observed during the manufacture and use of Trifluralin. | | Fire Hazard | Special Hazards of Combustion Products: Toxic and irritating hydrogen fluoride gas may be formed in fires. | | Agricultural Uses | Herbicide: 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 name | AGREFLAN®; 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 Profile | Moderately 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 Exposure | A potential danger to those involved
in the manufacture, formulation and application of this
selective, preemergence herbicide. | | Environmental Fate | Biological. 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 organics | Freely 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) | | Shipping | UN2588 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 evaluation | Technical 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. | | Incompatibilities | Trifluralin 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 Disposal | Dissolve 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). |
| | Trifluralin Preparation Products And Raw materials |
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