Diflufenican

Base Information

• Chemical Name: Diflufenican
• CAS No.: 83164-33-4
• Molecular Formula: C19H11F5N2O2
• Molecular Weight: 394.301
• European Community (EC) Number: 617-446-2,953-443-5
• UNII: 3T8D1VDO6K
• DSSTox Substance ID: DTXSID4041494
• Nikkaji Number: J246.562K
• Wikidata: Q424793
• Pharos Ligand ID: JSHMNFMBKYMK
• Metabolomics Workbench ID: 87125
• ChEMBL ID: CHEMBL1425995
• Mol file: 83164-33-4.mol

Synonyms:diflufenican

Chemical Property of Diflufenican

Chemical Property:

• Appearance/Colour: odorlessness white solid
• Vapor Pressure: 7.39E-06mmHg at 25°C
• Melting Point: 159-161 °C
• Refractive Index: 1.573
• Boiling Point: 376.2 °C at 760 mmHg
• PKA: 9.03±0.70(Predicted)
• Flash Point: 181.3 °C
• PSA: 51.22000
• Density: 1.438 g/cm³
• LogP: 5.49620
• Storage Temp.: 0-6°C
• Solubility.: Acetone (Slightly), Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly),
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 394.07406841
• Heavy Atom Count: 28
• Complexity: 533

Purity/Quality:

99% ^*data from raw suppliers

Diflufenican ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R52/53:
• Hazard Codes: R52/53:
• Statements: 52/53
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)OC2=C(C=CC=N2)C(=O)NC3=C(C=C(C=C3)F)F)C(F)(F)F
• Description: The diflufenican is a selective contact and residual herbicide that can be applied pre-emergence and post-emergence. It can be absorbed through the shoots of the germinating seeding with limited translocation. Its mode of mechanism is via a bleaching action through inhibiting the carotenoid biosynthesis process, further blocking photosynthesis process and causing plant death. It is used for the treatment of some broad leaved weeds such as Stellaria media (Chickweed), Veronica Spp (Speedwell), Viola spp, Geranium spp (Cranesbill) and Laminum spp (Dead nettles). It has been approved for use on barley, durum wheat, rye, triticale and wheat. It can be used in combination with isoproturon or other cereal herbicides.
• Uses: Pre and post emergence foliar absorbed herbicide for winter weed control in cereal crops; carotenoid biosynthesis inhibitor. Herbicide.

Technology Process of Diflufenican

There total 7 articles about Diflufenican 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: 88.0%

2,4-difluorophenylamine (367-25-9,76563-56-9) + 2-(3-Trifluoromethyl-phenoxy)-nicotinic acid (36701-89-0) → N-(2,4-difluorophenyl)-2-(3-trifluoromethylphenoxy)-3-pyridinecarboxamide (83164-33-4)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; Cooling with ice;

Reference yield: 33.0%

3-chloro-2-[3-(trifluoromethyl)phenoxy]pyridine (197565-66-5) + carbon monoxide (201230-82-2) + 2,4-difluorophenylamine (367-25-9,76563-56-9) → N-(2,4-difluorophenyl)-2-(3-trifluoromethylphenoxy)-3-pyridinecarboxamide (83164-33-4)

Guidance literature:

With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride; 1,4-di(diphenylphosphino)-butane; In xylene; at 190 - 195 ℃; for 19h; under 11251.1 Torr;

Reference yield:

N-(2-(4,5-dihydrooxazol-2-yl)phenyl)nicotinamide (1570135-74-8) → N-(2,4-difluorophenyl)-2-(3-trifluoromethylphenoxy)-3-pyridinecarboxamide (83164-33-4)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium carbonate / dimethyl sulfoxide / 8 h / 80 °C

2: sodium hydroxide; ethanol / 6 h / 80 °C

3: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Cooling with ice

With dmap; ethanol; sodium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In dichloromethane; dimethyl sulfoxide;

upstream raw materials:

3-chloro-2-[3-(trifluoromethyl)phenoxy]pyridine

carbon monoxide

2,4-difluorophenylamine

2-(3-Trifluoromethyl-phenoxy)-nicotinic acid

Refernces

• 1、 -. "Novel 2－ aryloxynicotinamide compound as well as preparation method and application thereof". Paragraph 0048-0052. . Retrieved 2020/03/17.
• 2、 -. "Solid mixtures based on sulfonylureas and adjuvants". . . Retrieved 2008/06/13.