60207-31-0

Basic information

• Product Name: Azaconazole
• Synonyms: AZACONAZOLE;1-[2-(2,4-DICHLOROPHENYL)-1,3-DIOXOLAN-2-YLMETHYL]-1H-1,2,4-TRIAZOLE;SAFETRAY SL;RODEWOD;4-triazole,1-((2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl)methyl)-1h-2;azoconozole;madurox;Azaconazol, Vetranal
• CAS NO: 60207-31-0
• Molecular Formula: C12H11Cl2N3O2
• Molecular Weight: 300.14
• EINECS: 262-102-3
• Mol File: 60207-31-0.mol

Chemical Properties

• Melting Point: 109.9°
• Boiling Point: 460.7 °C at 760 mmHg
• Flash Point: 232.4 °C
• Appearance: /
• Density: 1.51 g/cm³
• Vapor Pressure: 1.14E-08mmHg at 25°C
• Refractive Index: 1.658
• Storage Temp.: 0-6°C
• PKA: 2.94±0.12(Predicted)
• Water Solubility: 300 mg l-1 (20 °C)
• CAS DataBase Reference: Azaconazole(CAS DataBase Reference)
• NIST Chemistry Reference: Azaconazole(60207-31-0)
• EPA Substance Registry System: Azaconazole(60207-31-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 46
• WGK Germany: 1
• RTECS: XZ4605000
• Hazardous Substances Data: 60207-31-0(Hazardous Substances Data)

Usage

Uses

Used in Agriculture and Horticulture:
Azaconazole is used as a fungicide for the cultivation of ornamental crops, specifically to control canker and other diseases. Its application helps in protecting plants from wood-destroying and sapstain fungi, ensuring healthier growth and higher crop yields.
Used in Wood Protection:
Azaconazole serves as a fungicide for the protection of wood, preventing the growth of wood-destroying fungi that can cause structural damage and reduce the lifespan of wooden materials.
Used in Composite Wood Products:
Azaconazole is used as a preservative in the manufacturing of composite wood products, such as particleboard and plywood. Its application helps in preventing fungal infestations and decay, thereby enhancing the durability and longevity of these products.
Used in Mushroom Cultivation:
Azaconazole is utilized as a disinfectant in mushroom cultivation, ensuring a clean and healthy environment for the growth of mushrooms. This helps in reducing the risk of fungal contamination and improving the overall quality of the produce.
Used in Storage of Fruits and Vegetables:
Azaconazole is also used as a disinfectant on storage boxes for fruits and vegetables, preventing the growth of fungi that can cause spoilage and reduce the shelf life of these perishable items. This application helps in maintaining the freshness and quality of the stored produce for a longer duration.

Originator

Azaconazole,Chemical

Manufacturing Process

A stirred and cooled (0°C) solution of 1-(2,4-diaminophenyl)-1-ethanone in a concentrated hydrochloric acid solution, water and acetic acid was diazotated with a solution of sodium nitrite in water. After stirring at 0°C, the whole was poured onto a solution of copper (I) chloride in a concentrated hydrochloric acid solution while stirring. The mixture was heated at 60°C. After cooling to room temperature, the product was extracted twice with 2,2'-oxybispropane. The combined extracts were washed successively with water, a diluted sodium hydroxide solution and again twice with water, dried, filtered and evaporated, yielding 1-(2,4-dichlorophenyl)-1-ethanone. 1-(2,4-Dichlorophenyl)-1-ethanon were dissolved in 1,2-ethanediol at heating. While stirring bromine were added dropwise, without external heating. After stirring at room temperature, 4-methylbenzenesulfonic acid and benzene were added. The whole was stirred and refluxed overnight with water-separator. The reaction mixture was evaporated and the residue was taken up in 2,2'- oxybispropane. The resulting solution was washed successively once with a dilute sodium hydroxide solution and 3 times with water, dried, filtered and evaporated. The residue was distilled, yielding 2-(bromomethyl)-2-(2,4- dichlorophenyl)-1,3-dioxolane. 6.9 parts of 1H-1,2,4-triazole in 150 parts of dimethylformamide were added to a stirred solution of 2.3 parts of sodium in 120 parts of methanol. The methanol was removed at normal pressure until the internal temperature of 130°C was reached. Then, 25 parts of 2-(bromomethyl)-2-(2,4- dichlorophenyl)-1,3-dioxolane were added. The reaction-mixture was stirred and refluxed for 3 h. It was allowed to cool to room temperature and poured onto water. The precipitated product was filtered off, yielding 12 parts of 1-[2- (2,4-dichlorophenyl)-1,3-dioxolan-2-yl-methyl]-1H-1,2,4-triazole, melting point 109.9°C (crystallized from diisopropylether, activated charcoal).

Therapeutic Function

Antifungal

Metabolic pathway

Little published dormation is available on the metabolism of azaconazole.

Degradation

Azaconazole is stable to light under normal storage conditions (but not in ketonic solvents). It is stable at temperatures up to 220 °C.

InChI:InChI=1/C12H11Cl2N3O2/c13-9-1-2-10(11(14)5-9)12(18-3-4-19-12)6-17-8-15-7-16-17/h1-2,5,7-8H,3-4,6H2

Synthetic route

1,2,4-Triazole (288-88-0) + 2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane → azaconazole (60207-31-0)

Conditions	Yield
Stage #1: 1,2,4-Triazole With sodium In methanol at 20℃; for 0.5h; Stage #2: 2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane With potassium iodide for 3h; Reflux;	59.98%
Stage #1: 1,2,4-Triazole With sodium In methanol at 20℃; for 0.5h; Stage #2: 2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane With potassium iodide In N,N-dimethyl-formamide at 130℃; for 3h;	59.98%
With sodium In N-methyl-acetamide; methanol

ethylene glycol (107-21-1) + 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (58905-16-1) → azaconazole (60207-31-0)

Conditions	Yield
With toluene-4-sulfonic acid In pentan-1-ol for 20h; Reflux;	56.7%
With toluene-4-sulfonic acid In 5,5-dimethyl-1,3-cyclohexadiene; pentan-1-ol for 20h; Reflux;	56.7%

1-(2,4-dichlorophenyl)-2-(4-amino-4H-1,2,4-triazolyl)ethanone hydrochloride → azaconazole (60207-31-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride; sodium nitrite / water / 0 - 5 °C 2: toluene-4-sulfonic acid / pentan-1-ol / 20 h / Reflux View Scheme

1-(2,4-dichlorophenyl)ethan-1-one (2234-16-4) → azaconazole (60207-31-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: bromine / butan-1-ol / 2 h / 20 °C 1.2: 4 h / Reflux 2.1: sodium / methanol / 0.5 h / 20 °C 2.2: 3 h / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride; bromine / diethyl ether / Cooling with ice 2.1: toluene-4-sulfonic acid / butan-1-ol; benzene / 6 h / Reflux 3.1: sodium / methanol / 0.5 h / 20 °C 3.2: 3 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: aluminum (III) chloride; chlorine / diethyl ether / Cooling with ice 2: isopropyl alcohol / 4 h / Reflux 3: toluene-4-sulfonic acid / pentan-1-ol / 20 h / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / benzene; butan-1-ol / 6 h / 86 - 87 °C 2.1: bromine / 20 °C 3.1: sodium / methanol / 0.5 h / 20 °C 3.2: 3 h / 130 °C View Scheme
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride; bromine / diethyl ether / Cooling with ice 2.1: toluene-4-sulfonic acid / benzene; butan-1-ol / 5 h / 87 - 88.5 °C 3.1: sodium / methanol / 0.5 h / 20 °C 3.2: 3 h / 130 °C View Scheme

2,4-dichlorophenacyl bromide (2631-72-3) → azaconazole (60207-31-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid / butan-1-ol; benzene / 6 h / Reflux 2.1: sodium / methanol / 0.5 h / 20 °C 2.2: 3 h / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid / benzene; butan-1-ol / 5 h / 87 - 88.5 °C 2.1: sodium / methanol / 0.5 h / 20 °C 2.2: 3 h / 130 °C View Scheme

2,2',4'-trichloroacetophenone (4252-78-2) → azaconazole (60207-31-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: isopropyl alcohol / 4 h / Reflux 2: toluene-4-sulfonic acid / pentan-1-ol / 20 h / Reflux View Scheme

1,3-Dichlorobenzene (541-73-1) → azaconazole (60207-31-0)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / 1,2-dichloro-benzene / 0.33 h 1.2: Cooling with ice 2.1: bromine / butan-1-ol / 2 h / 20 °C 2.2: 4 h / Reflux 3.1: sodium / methanol / 0.5 h / 20 °C 3.2: 3 h / Reflux View Scheme
Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / 1,2-dichloro-benzene / 0.33 h 1.2: Cooling with ice 2.1: aluminum (III) chloride; chlorine / diethyl ether / Cooling with ice 3.1: isopropyl alcohol / 4 h / Reflux 4.1: toluene-4-sulfonic acid / pentan-1-ol / 20 h / Reflux View Scheme
Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / 1,2-dichloro-benzene / 0.33 h 1.2: Cooling with ice 2.1: aluminum (III) chloride; bromine / diethyl ether / Cooling with ice 3.1: toluene-4-sulfonic acid / butan-1-ol; benzene / 6 h / Reflux 4.1: sodium / methanol / 0.5 h / 20 °C 4.2: 3 h / Reflux View Scheme

C10H10Cl2O2 → azaconazole (60207-31-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: bromine / 20 °C 2.1: sodium / methanol / 0.5 h / 20 °C 2.2: 3 h / 130 °C View Scheme

1-(2,4-dichlorophenyl)-2-(4-amino-4H-1,2,4-triazoliumyl)ethanone chloride (118227-30-8) → azaconazole (60207-31-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride; sodium nitrite / water / 0 - 20 °C 2: toluene-4-sulfonic acid / pentan-1-ol; 5,5-dimethyl-1,3-cyclohexadiene / 20 h / Reflux View Scheme

azaconazole (60207-31-0) → 1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole nitrate

Conditions	Yield
With nitric acid In di-isopropyl ether	3.0 g
With nitric acid In di-isopropyl ether Cooling;	3 g

azaconazole (60207-31-0) → 1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole sulfate

Conditions	Yield
With sulfuric acid In di-isopropyl ether	6.4 g
With sulfuric acid In di-isopropyl ether	6.4 g

Upstream product

• 288-88-0 1,2,4-Triazole 
• 107-21-1 ethylene glycol 
• 58905-16-1 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone 
• 2234-16-4 1-(2,4-dichlorophenyl)ethan-1-one 
• 2631-72-3 2,4-dichlorophenacyl bromide 
• 4252-78-2 2,2',4'-trichloroacetophenone 
• 541-73-1 1,3-Dichlorobenzene 
• 84946-10-1 C₁₀H₁₀Cl₂O₂ 
• 118227-30-8 1-(2,4-dichlorophenyl)-2-(4-amino-4H-1,2,4-triazoliumyl)ethanone chloride 

Relevant articles and documents

Method for synthesizing azaconazole through 4-amino-4H-1,2,4-triazole alkylation

The invention discloses a method for synthesizing azaconazole through 4-amino-4H-1,2,4-triazole alkylation. The method comprises step 1, preparing a raw material which is shown in a following image; step 2, synthesizing 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazole-1-yl) ethanone; step 3, synthesizing azaconazole. The method disclosed by the invention has the advantages that development of a novel azaconazole bactericide successfully fills the blank in China, synthesis researches of similar derivatives based on the azaconazole bactericide will be in the ascendant, and successful development andindustrial implementation of varieties of novel bactericides have a far-reaching influence on national economy development. The method disclosed by the invention is an azaconazole synthesizing method.

Synthesis method of azaconazole intermediate

The invention discloses a synthesis method of an azaconazole intermediate. The synthesis method mainly comprises a synthesis method of 2,4-dichloroacetophenone, a synthesis method of 2-bromo-1-(2,4-dichlorophenyl) ethyl ketone, and a synthesis method of ketal. The preparation method has the advantages that the development of the novel azaconazole bactericide fills up a domestic blank in the field,similar derivative synthesis research based on the synthesis method is in the ascendant, and successful development and industrial implementation of various novel bactericides can be realized. The invention provides a novel azaconazole synthesis method.

3-phenyl-pyrones

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Utilization of 3-phenyl-pyrones for pest control

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Arylphenyl-substituted cyclic keto enols

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Compositions and methods of treatment for cancer or viral infections

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Halogen pyrimidines and its use thereof as parasite abatement means

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Iminoacetic acid amides and their use as pest control agents

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Alkoxyacrylic acid thiol esters used as fungicides

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Hydrazonoacetic acid amides and the use thereof as pesticides

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