Fluazinam

Base Information

• Chemical Name: Fluazinam
• CAS No.: 79622-59-6
• Deprecated CAS: 1135442-54-4,113015-31-9,160170-67-2
• Molecular Formula: C13H4Cl2F6N4O4
• Molecular Weight: 465.096
• Hs Code.: 29333990
• European Community (EC) Number: 616-712-5
• UNII: 0P91PCK33Q
• DSSTox Substance ID: DTXSID7032551
• Nikkaji Number: J120.417C
• Wikipedia: Fluazinam
• Wikidata: Q2202504
• Metabolomics Workbench ID: 143657
• ChEMBL ID: CHEMBL1878267
• Mol file: 79622-59-6.mol

Synonyms:3-chloro-N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-2-pyridinamine;fluazinam

Chemical Property of Fluazinam

Chemical Property:

• Appearance/Colour: Light yellow crystals
• Vapor Pressure: 7.41E-06mmHg at 25°C
• Melting Point: 113 °C
• Refractive Index: 1.571
• Boiling Point: 376.1 °C at 760 mmHg
• PKA: 7.11(at 25℃)
• Flash Point: 181.3 °C
• PSA: 116.56000
• Density: 1.766 g/cm³
• LogP: 7.10540
• Storage Temp.: 2-8°C
• Water Solubility.: 1.7 mg l-1 (25 °C)
• XLogP3: 6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 2
• Exact Mass: 463.9513790
• Heavy Atom Count: 29
• Complexity: 628

Purity/Quality:

99% ^*data from raw suppliers

Fluazinam ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T;N,N,T,Xn,F
• Statements: 23-41-43-50/53-36-20/21/22-11-38-20-63
• Safety Statements: 26-36/37/39-45-60-61-36/37-16-63-57-56-38-28-27-24/25-20/21-13

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Fungicides
• Canonical SMILES: C1=C(C=NC(=C1Cl)NC2=C(C=C(C(=C2[N+](=O)[O-])Cl)C(F)(F)F)[N+](=O)[O-])C(F)(F)F
• Description: Fluazinam is a protective broad-spectrum contact fungicide registered for agricultural use to control various soil-borne fungal pathogens on a variety of crops, such as peanuts, potatoes, beans, etc. It can be applied as a foliar spray or soil treatment, which is effective against a number of diseases caused by pathogenic fungi such as gray mold, downy mildew, melanose, scab, alternaria blotch, clubroot, sclerotinia blight, white root rot, violet root rot. Besides, it shows acaricidal property, which can fight against mites in citrus. However, as a protective agent, fluazinam is neither systemic or curative, which functions by inhibiting spore germination and spore growth, and also the development of infection structures, thereby giving it protective action with a good residual effect. The anti-fungal property of fluazinam acts by disrupting the energy production of the fungus at multiple sites and therefore preventing resistance. Fluazinam, with a LogP of 3.56, has very low solubility in water (1.7 mgL?1, pH6.8, 25?C) but higher solubilities in organic solvents (e.g., acetone 470 g/L, dichloromethane 330 g/L, ethanol 150 g/L, all at 20 ?C). The active ingredient forms light yellow crystals with an MP of 115 to 117 ?C and has a vp of 1.5 mPa (25 ?C). The compound is stable to acid, alkali, and heat (5).
• uses: Fluazinam is a pyridinamine fungicide that can control blight caused by Phytophthora infestans in potatoes, beans and other crops (e.g., bushberries, edible-podded beans and cruciferous vegetables such as cabbage and broccoli). Fluazinam has strong persistence of effect against blight and can suppress secondary infection in the field through inhibition of sporulation. Fluazinam has been widely used in the U.S. since the 1990s. Fluazinam is not registered for use in California. Exposure in California would occur mainly through crops imported from other states.
• Uses: Fluazinam is a broad spectrum fungicide. Fluazinam is commonly used for control of Sclerotinia blight and other soilborne pathogens of peanut as well for the control of potato blight. Fluazinam, discovered and developed by ISK, is a highly active fungicide with broad spectrum activity, including soil borne diseases. Furthermore, it has acaricidal activity. Fluazinam is a multi-site contact fungicide that belongs to the pyridinamine family. Fluazinam has launched in several countries since its commercialization in the early 1990's. Now Fluazinam has established a strong presence in potato late blight, soybean white mold or turf fungicide market. Fluazinam is a fungicide with a protective action but with little curative or systemic activity. It is used to control grey mould and downy mildew on vines, apple scab, southern blight and white mould on peanuts and Phytophthora infestans and tuber blight on potatoes. It is also used against clubroot on crucifers, rhizomania on sugar beet and mites in apples.

Technology Process of Fluazinam

There total 10 articles about Fluazinam 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: 98.5%

2,4-dichloro-3,5-dinitro-benzotrifluoride (29091-09-6) + 2-amino-3-chloro-5-(trifluoromethyl)pyridine (79456-26-1) → fluazinam (79622-59-6)

Guidance literature:

With potassium hydroxide; In 2-methyltetrahydrofuran; at 20 ℃; for 4h; Concentration; Temperature; Solvent;

Reference yield: 97.5%

C13H5ClF6N4O4 → fluazinam (79622-59-6)

Guidance literature:

With sulfuryl dichloride; In acetonitrile; at 40 - 75 ℃; for 5h; Reagent/catalyst; Temperature;

Reference yield:

nicotinic acid (59-67-6) → fluazinam (79622-59-6)

Guidance literature:

Multi-step reaction with 4 steps

1: phosphorus pentachloride / 14 h / 210 °C / 1500.15 - 27752.8 Torr / Autoclave

2: hydrogen fluoride; iron(III) chloride; pyridine / 130 - 175 °C / Autoclave

3: ammonia / water / 9 h / 80 °C / 13501.4 - 16501.7 Torr / Autoclave

4: potassium hydroxide / acetonitrile / 6.25 h / 5 - 40 °C

With pyridine; iron(III) chloride; phosphorus pentachloride; hydrogen fluoride; ammonia; potassium hydroxide; In water; acetonitrile;

upstream raw materials:

2,4-dichloro-3,5-dinitro-benzotrifluoride

2-amino-3-chloro-5-(trifluoromethyl)pyridine

3-trichloromethyl-pyridine

nicotinic acid

Refernces

• 1、 -. "Method for synthesizing fluazinam (by machine translation)". Paragraph 0016-0018. . Retrieved 2019/08/12.
• 2、 -. "Preparation method for fluazinam". Paragraph 0042; 0062-0073. . Retrieved 2019/01/05.