Trifluralin

Base Information

• Chemical Name: Trifluralin
• CAS No.: 1582-09-8
• Deprecated CAS: 39300-53-3,52627-52-8,61373-95-3,75635-23-3,71281-30-6,52627-52-8,71281-30-6,75635-23-3
• Molecular Formula: C13H16F3N3O4
• Molecular Weight: 335.283
• Hs Code.: 29214300
• European Community (EC) Number: 216-428-8
• ICSC Number: 0205
• UN Number: 3077
• UNII: C8BX46QL7K
• DSSTox Substance ID: DTXSID4021395
• Nikkaji Number: J3.672B
• Wikipedia: Trifluralin
• Wikidata: Q418247
• Metabolomics Workbench ID: 144282
• ChEMBL ID: CHEMBL31970
• Mol file: 1582-09-8.mol

Synonyms:Treflan;Trifluralin

Chemical Property of Trifluralin

Chemical Property:

• Appearance/Colour: Yellow-orange crystalline solid
• Vapor Pressure: 1.21E-05mmHg at 25°C
• Melting Point: 48.5 °C
• Refractive Index: 1.527
• Boiling Point: 369.1 °C at 760 mmHg
• PKA: -1.45±0.50(Predicted)
• Flash Point: 177 °C
• PSA: 94.88000
• Density: 1.337 g/cm³
• LogP: 5.19460
• Storage Temp.: APPROX 4°C
• Water Solubility.: <0.01 g/100 mL at 22.5℃
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 335.10929049
• Heavy Atom Count: 23
• Complexity: 392
• Transport DOT Label: Class 9

Purity/Quality:

98+% ^*data from raw suppliers

Trifluralin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi;N,N,Xi,Xn,F
• Statements: 36-43-50/53-20/21/22-11-40
• Safety Statements: 2-24-37-60-61-36-26-16-46-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Herbicides, Nitroaromatic
• Canonical SMILES: CCCN(CCC)C1=C(C=C(C=C1[N+](=O)[O-])C(F)(F)F)[N+](=O)[O-]
• Inhalation Risk: A nuisance-causing concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance is irritating to the eyes.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the kidney and liver. Tumours have been detected in experimental animals but may not be relevant to humans.
• 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. 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.
• Uses: Preemergence herbicide for controlling many grasses and broad-leaved weeds. Pre-emergence herbicide used for grass control in crops. 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.

Technology Process of Trifluralin

There total 6 articles about Trifluralin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C17H26F3N4O4(1-)*K(1+) (79871-51-5) → 2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine (1582-09-8,71281-30-6,75635-23-3,89300-31-2) + N-butylamine (109-73-9,85404-21-3)

Guidance literature:

With water; In dimethyl sulfoxide; Equilibrium constant;

DOI:10.1021/jo00341a028

Reference yield:

4-chloro-3,5-dinitrobenzotrifluoride (393-75-9) + di-n-propylamine (142-84-7) → 2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine (1582-09-8,71281-30-6,75635-23-3,89300-31-2)

Guidance literature:

Reflux;

DOI:10.1016/j.bmcl.2010.07.003

Reference yield:

4-chloro-3,5-dinitrobenzotrifluoride (393-75-9) → 2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine (1582-09-8,71281-30-6,75635-23-3,89300-31-2)

Guidance literature:

In water;

upstream raw materials:

C₁₃H₁₇F₃N₃O₅^(1-)

C₁₇H₂₆F₃N₄O₄^(1-)*K⁽¹⁺⁾

C₁₈H₂₆F₃N₄O₄^(1-)*K⁽¹⁺⁾

4-chloro-3,5-dinitrobenzotrifluoride

Downstream raw materials:

1-Dipropylamino-2,6-dinitro-4-tribrommethyl-benzol

2-ethyl-4-nitro-6-(trifluoromethyl)-1H-benzimidazole

α,α,α-trifluoro-2,6-dinitro-N-propyl-p-toluidine

α,α,α-trifluoro-2,6-diamino-N,N-dipropyl-p-toluidine

Refernces

• 1、 -. "Synthesis method of trifluralin". Paragraph 0021-0038. . Retrieved 2020/02/20.
• 2、 -. "Synergistic herbicidal mixtures". . . Retrieved 2008/06/13.