76674-21-0

Basic information

• Product Name: Flutriafol
• Synonyms: 1H-1,2,4-Triazole-1-ethanol, .alpha.-(2-fluorophenyl)-.alpha.-(4-fluorophenyl)-;flutriafol (ansi,bsi,iso);flutriafol solution;FLUTRIAFOLE;ALTOSUPER;1-(2-Fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol;1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1,2,4-triazol-1-yl)ethanol;Flutriafol 100mg [76674-21-0]
• CAS NO: 76674-21-0
• Molecular Formula: C₁₆H₁₃F₂N₃O
• Molecular Weight: 301.29
• Product Categories: Alpha sort;ConazolesPesticides&Metabolites;E-GAlphabetic;F;FA - FL;Fungicides;Pesticides;Agriculture
• Mol File: 76674-21-0.mol

Chemical Properties

• Melting Point: 130°
• Boiling Point: 506.5 °C at 760 mmHg
• Flash Point: 2 °C
• Appearance: solid
• Density: 1.3015 (estimate)
• Vapor Pressure: 4.43E-11mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 11.60±0.29(Predicted)
• Water Solubility: 130 mg l-1 (pH 7,20 °C)
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 13,4240
• BRN: 8155287
• CAS DataBase Reference: Flutriafol(CAS DataBase Reference)
• NIST Chemistry Reference: Flutriafol(76674-21-0)
• EPA Substance Registry System: Flutriafol(76674-21-0)

Safety Data

• Hazard Codes: Xn,F
• Statements: 22-36-20/21/22-11
• Safety Statements: 22-24/25-36-26
• RIDADR: UN 1648 3/PG 2
• WGK Germany: 3
• RTECS: XZ4825000
• Hazardous Substances Data: 76674-21-0(Hazardous Substances Data)

Usage

Metabolic pathway

Flutriafol is stable to hydrolysis and to light and it is persistent in soils. In crops, the metabolites identified were derivatives of triazole.

Degradation

Flutriafol, 1, is stable to hydrolysis at pH 5,7 and 9 in water at 50 °C over a period of 30 days in the dark. [14C-friazole]Flutriafoaln d [14C-carbinol]flutriafol were applied at a rate equivalent to 94 g ai ha-1 to samples of dry sandy loam soil distributed as a thin layer on 10 cm diameter glass plates. Samples were exposed to natural sunlight for 30 days or to alternating periods of 'black light' and darkness for 7 days. Recovery was 60-47% of applied radioactivity after 7 days artificial illumination and 74-85% after exposure to natural sunlight. All degradation products accounted for ＜5 %of the total applied radioactivity (PSD, 1996).

InChI:InChI=1/C16H13F2N3O/c17-13-7-5-12(6-8-13)16(22,9-21-11-19-10-20-21)14-3-1-2-4-15(14)18/h1-8,10-11,22H,9H2

Synthetic route

1,2,4-Triazole (288-88-0) + 1-(2-fluorophenyl)-1-(4-fluorophenyl)ethylene oxide → flutriafol (76674-21-0)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 140℃; for 0.333333h; Temperature;	93.5%
With dimethyl sulfoxide at 130 - 140℃; for 2h; Temperature; Green chemistry;	186 g

2,4'-difluorobenzophenone (342-25-6) → flutriafol (76674-21-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: dimethyl sulfoxide / Heating; Green chemistry 1.2: 3 h / 30 - 40 °C / Green chemistry 2.1: dimethyl sulfoxide / 2 h / 130 - 140 °C / Green chemistry View Scheme

flutriafol (76674-21-0) → (S)-(+)-flutriafol (586965-70-0) + (R)-flutriafol

Conditions	Yield
In methanol; water; acetonitrile at 20℃; Reagent/catalyst; Solvent; Resolution of racemate;

Upstream product

• 288-88-0 1,2,4-Triazole 
• 88374-05-4 1-(2-fluorophenyl)-1-(4-fluorophenyl)ethylene oxide 
• 342-25-6 2,4'-difluorobenzophenone 

Downstream Products

• 586965-70-0 (S)-(+)-flutriafol 
• 87676-93-5 (R)-flutriafol 

Relevant articles and documents

Continuous preparation method of flutriafol

The invention relates to a continuous preparation method of flutriafol. 1,2,4-triazole and 1-(2-fluorophenyl)-1-(4-fluorophenyl) ethylene oxide react in a microchannel continuous flow reactor in the presence of an organic solvent and a soluble alkali to obtain the flutriafol. The method is short in reaction time and high in automatic production level, promotes the competitiveness of an enterprise,is small in safety hazard in the process of synthesizing the target product, reduces the risk coefficient, is high in yield of the target product, simple in post treatment and little in solid waste,and realizes a cleaner and environment-friendly production process.

A synthesis method of flutriafol (by machine translation)

The invention relates to a synthesis method of flutriafol, the halogenated methane and dimethyl sulfoxide in the 0 - 120 °C reaction under 1 - 48 H-; adding solid alkali and 2, 4' - difluoro benzophenone, temperature control in the 0 - 80 °C, reaction 1 - 25 the H; adding triazole, temperature control in the 50 - 200 °C, reaction 1 - 20 the H, after the reaction, filtered, to remove solvent, washing, crystallization get said teflubenzuron. In the present invention dimethyl sulfoxide is used as the reaction raw material, but also as the solvent, avoiding mixed solvent separation difficulties, and, dimethyl sulfoxide and halogenated methane to replace the existing technology to the environment in the pressure of the dimethyl sulfide and highly toxic chemicals dimethyl sulfate, so that the present invention is friendly to the environment, in addition, the invention mild reaction conditions, the reaction time is short, high yield, high product quality, three waste emissions low, produces only a sole inorganic salt, of the present invention thereby the productivity is high, economic efficiency is good. (by machine translation)

FUNGICIDAL MIXTURES

The present invention relates to fungicidal mixtures comprising, as active components, 1) azolylmethyloxiranes of the general formula I wherein the variables have the meanings described in the application, 2) a fungicidal compound II, and 3) optionally a further fungicidal compound II, where the compounds II of components 2 and 3 independently of one another are selected from the group consisting of the compounds described in the application, with the proviso that components 2 and 3 are not identical, and to the use of the fungicidal mixtures for controlling phytopathogenic fungi and to the compositions comprising them.

FUNGICIDAL MIXTURES

The present invention relates to fungicidal mixtures comprising, as active components, 1) azolylmethyloxiranes of the general formula I in which the variables have the meanings described in the application, and 2) a fungicidal compound II, where the compounds II of component 2 are selected from among the compounds described in the application, and to the use of the fungicidal mixtures for controlling phytopathogenic fungi and to the compositions comprising them.

Fungicide compositions

Compositions of azole fungicides exhibiting reduced eye irritation are prepared by replacing a significant portion of the hydrocarbon solvent with a combination of propylene glycol and a long chain fatty alcohol.

Isomerization process

Transformation of specified 4H-substituted-1,2,4-triazoles into their 1H-substituted isomers by heating at a temperature of 150° C. to 300° C. in the presence of a base and, essentially, in the absence of a polar aprotic solvent.

Fungicide compositions

A fungicide composition having reduced eye irritation comprising in percent by weight based on the weight of the composition 5-50% of an azole fungicide which irritates the eye in combination with an aromatic hydrocarbon, 20-40% propylene glycol, 1-20% fatty alcohol having at least 10 carbon atoms, 10-40% surfactant and less than about 20% aromatic hydrocarbon.