Related Searches: trifluralin

trifluralin(CAS No. 1582-09-8)

trifluralin C13H16F3N3O4 (cas 1582-09-8) Molecular Structure

1582-09-8 Structure

Identification and Related Records

【Name】
trifluralin
【CAS Registry number】
1582-09-8
【Synonyms】
alpha,alpha,alpha-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine
Trifurex
TRIFLUREX
trilin 4ec
Trifiuralin
treflam
TREFLAN
TREFLAN(R)
【EINECS(EC#)】
216-428-8
【Molecular Formula】
C13H16F3N3O4 (Products with the same molecular formula)
【Molecular Weight】
335.28
【Inchi】
InChI=1/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
【Canonical SMILES】
CCCN(CCC)C1=C(C=C(C=C1[N+](=O)[O-])C(F)(F)F)[N+](=O)[O-]
【MOL File】
1582-09-8.mol

Chemical and Physical Properties

【Appearance】
Yellow-orange crystalline solid
【Density】
1.294
【Melting Point】
48.5℃
【Boiling Point】
139℃
【Vapour】
1.21E-05mmHg at 25°C
【Refractive Index】
1.527
【Flash Point】
177°C
【Water】
<0.01 g/100 mL at 22.5 ºC
【Solubilities】
<0.01 g/100 mL at 22.5 oC in water
【Color/Form】
Yellow crystals
YELLOW-ORANGE PRISMS
【Stability】
Shelf life of concentrate is more than 2 yr stable in pure state, in liquidor in granular formulations stable though susceptible to decomposition by ultraviolet radiation.
【Storage temp】
APPROX 4°C
【Spectral properties】
Intense mass spectral peaks: 306 m/z (100%), 264 m/z (97%), 43 m/z (95%), 41 m/z (35%)
【Computed Properties】
Molecular Weight:335.27905 [g/mol]
Molecular Formula:C13H16F3N3O4
XLogP3:5.3
H-Bond Donor:0
H-Bond Acceptor:8
Rotatable Bond Count:5
Exact Mass:335.109291
MonoIsotopic Mass:335.109291
Topological Polar Surface Area:94.9
Heavy Atom Count:23
Formal Charge:0
Complexity:392
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:4
Feature 3D Anion Count:2
Feature 3D Cation Count:1
Feature 3D Hydrophobe Count:2
Feature 3D Ring Count:1
Effective Rotor Count:8
Conformer Sampling RMSD:0.8
CID Conformer Count:2

Safety and Handling

【Hazard Codes】
Xi:Irritant
【Risk Statements】
R36;R43;R50/53
【Safety Statements 】
S2;S24;S37;S60;S61
【Safety】

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 F? and NOx. See also?FLUORIDES.
Hazard Codes:?IrritantXi,DangerousN,HarmfulXn,FlammableF
Risk Statements: 36-43-50/53-20/21/22-11
?R36:Irritating to eyes.?
R43:May cause sensitization by skin contact.?
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.?
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.?
R11:Highly flammable.
Safety Statements: 2-24-37-60-61-36-26-16?
S2:Keep out of the reach of children.?
S24:Avoid contact with skin.?
S37:Wear suitable gloves.?
S60:This material and its container must be disposed of as hazardous waste.?
S36:Wear suitable protective clothing.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S16:Keep away from sources of ignition.
RIDADR: UN 2588
RTECS: XU9275000
Hazardous Substances Data: 1582-09-8(Hazardous Substances Data)

【Skin, Eye, and Respiratory Irritations】
Cause eye irritation. May cause skin sensitization reactions in certain individuals.
【Transport】
UN 2588
【Fire Potential】
TECHNICAL MATERIAL IS NOT FLAMMABLE. FOR FORMULATED CONCENTRATE USE ORDINARY PRECAUTIONS FOR VOLATILE SOLVENTS.
【Formulations/Preparations】
USEPA/OPP Pesticide Code 036101; Trade Names: Treflan.
EMULSIFIABLE CONCENTRATE (4 LB TRIFLURALIN PER US GAL), GRANULAR 5%. PRODUCT TO CONTAIN LESS THAN 1 PPM NITROSAMINE BY EPA ORDER.
【Other Preventative Measures】
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
【Protective Equipment and Clothing】
Cause eye irritation. May cause skin sensitization reactions in certain individuals.
【Specification】

usageEng:Pre-emergence herbicide used for grass control in crops.
Safety Statements:2-24-37-60-61-36-26-16
2:Keep out of the reach of children
24:Avoid contact with skin
37:Wear suitable gloves
60:This material and/or its container must be disposed of as hazardous waste
61:Avoid release to the environment. Refer to special instructions safety data sheet
36:Wear suitable protective clothing
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
16:Keep away from sources of ignition - No smoking
【Octanol/Water Partition Coefficient】
log Kow= 5.34
【Report】

NCI Carcinogenesis Bioassay (feed); Clear Evidence: mouse NCITR* ?? National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-34 ,1978. ; No Evidence: rat NCITR* ?? National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-34 ,1978. . EPA Genetic Toxicology Program. Community Right-To-Know List.

【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
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.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

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

(1972) 1.82X10+9 GRAMS
U.S. Imports

(1972) NEGLIGIBLE
U.S. Production

(1972) 9.53X10+9 GRAMS
Consumption Patterns

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)
【Usage】

Herbicide.

Biomedical Effects and Toxicity

【Pharmacological Action】
- 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.
【Therapeutic Uses】
Pre-emergence herbicide used for grass control in crops.
【Biomedical Effects and Toxicity】
APPROX 80% OF INGESTED CMPD WAS EXCRETED IN FECES, REMAINDER IN URINE /OF RATS & DOGS STUDIED/.
SALMON PARR SALMO SALAR WERE SUBJECTED TO HIGH INITIAL CONCN OF TRIFLURALIN & THEN MAINTAINED IN CLEAR WATER FOR 12 MO. SOME WERE REMOVED AT PRESELECTED INTERVALS FOR EXAM BY X-RAY & CHEM ANALYSIS. HALF-LIFE OF TRIFLURALIN IN SALMON PARR WAS 40.5 DAYS.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TRIFLURALIN WAS MORE PERSISTENT IN SOIL (PH 6.56) THAN METRIBUZIN. HALF-LIFE OF TRIFLURALIN WAS 38 DAYS FOR 670 G/HA & 61 DAYS FOR 1100 G/HA.
TERRESTRIAL FATE: Based on a classification scheme(1), experimental Koc values ranging from 397 to 16,851(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 known to rapidly volatilize from both moist and dry soils to the atmosphere(10-13), although the volatilization rate is greater for moist soils(14). Trifluralin was volatilized 16%, 28% and 40% in dry, moist and flooded soils over a 32 day incubation period(10). The persistence of trifluralin in soil has been estimated at 6 months(16) and >40 weeks(15). Its persistence is less in southern climates than in northern ones(16).
AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 397 to 16,851(2-8) indicate trifluralin is expected to adsorb to suspended solids and sediment. Volatilization from water surfaces may be expected(9) based upon experimental data(10) and a Henry's Law constant of 1.03X10-4 atm-cu m/mole(12), although its strong adsorption to sediment and suspended organic matter may attenuate the rate of this process(SRC). Using this Henry's Law constant and an estimation method(9), volatilization half-lives for a model river and model lake are 0.5 days and 12 days, respectively, when adsorption is ignored(SRC). Trifluralin is not expected to hydrolyze in water(11). According to a classification scheme(13), experimental BCF factors ranging from 1,689 to 9,586(14-17) suggest the potential for bioconcentration in aquatic organisms is very high. 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).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trifluralin, which has an experimental vapor pressure of 4.58X10-5 mm Hg(2) at 25 deg 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 24X10-12 cu cm/molecule-sec at 25 deg C(SRC), determined using a structure estimation method(3). Particulate-phase trifluralin may be removed from the air by wet and dry deposition(SRC). If released to the atmosphere, trifluralin is expected to undergo rapid photolytic degradation; the observed half-life for trifluralin in July sunlight ranged from 25-60 min(4). In the presence of ozone, the rate of this reaction increases(5,6).

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