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60207-31-0

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60207-31-0 Usage

Originator

Azaconazole,Chemical

Uses

Different sources of media describe the Uses of 60207-31-0 differently. You can refer to the following data:
1. Fungicide for cultivation on wood; preservative for composite wood products.
2. Azaconazole is particularly active against wood-destroying and sapstain fungi. It is also used as a disinfectant in mushroom cultivation and on storage boxes for fruit and vegetables.

Definition

ChEBI: A member of the class of dioxolanes that is 1,3-dioxolane substituted at position 2 by 2,4-dichlorophenyl and 1,2,4-triazol-1-ylmethyl groups. A fungicide used mainly in ornamental crops to control canker and other diseases. Azaconazole is moderately toxic to mammals but is not expected to bioaccumulate. It is moderately toxic to birds, fish and aquatic invertebrates.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 60207-31-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,0,2,0 and 7 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 60207-31:
(7*6)+(6*0)+(5*2)+(4*0)+(3*7)+(2*3)+(1*1)=80
80 % 10 = 0
So 60207-31-0 is a valid CAS Registry Number.
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

60207-31-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name azaconazole

1.2 Other means of identification

Product number -
Other names 1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:60207-31-0 SDS

60207-31-0Synthetic route

1,2,4-Triazole
288-88-0

1,2,4-Triazole

2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane

2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane

azaconazole
60207-31-0

azaconazole

Conditions
ConditionsYield
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

ethylene glycol

1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone
58905-16-1

1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone

azaconazole
60207-31-0

azaconazole

Conditions
ConditionsYield
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

1-(2,4-dichlorophenyl)-2-(4-amino-4H-1,2,4-triazolyl)ethanone hydrochloride

azaconazole
60207-31-0

azaconazole

Conditions
ConditionsYield
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

1-(2,4-dichlorophenyl)ethan-1-one

azaconazole
60207-31-0

azaconazole

Conditions
ConditionsYield
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

2,4-dichlorophenacyl bromide

azaconazole
60207-31-0

azaconazole

Conditions
ConditionsYield
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

2,2',4'-trichloroacetophenone

azaconazole
60207-31-0

azaconazole

Conditions
ConditionsYield
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

1,3-Dichlorobenzene

azaconazole
60207-31-0

azaconazole

Conditions
ConditionsYield
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

C10H10Cl2O2

azaconazole
60207-31-0

azaconazole

Conditions
ConditionsYield
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

1-(2,4-dichlorophenyl)-2-(4-amino-4H-1,2,4-triazoliumyl)ethanone chloride

azaconazole
60207-31-0

azaconazole

Conditions
ConditionsYield
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

azaconazole

1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole nitrate

1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole nitrate

Conditions
ConditionsYield
With nitric acid In di-isopropyl ether3.0 g
With nitric acid In di-isopropyl ether Cooling;3 g
azaconazole
60207-31-0

azaconazole

1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole sulfate

1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole sulfate

Conditions
ConditionsYield
With sulfuric acid In di-isopropyl ether6.4 g
With sulfuric acid In di-isopropyl ether6.4 g

60207-31-0Downstream Products

60207-31-0Relevant articles and documents

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

-

Paragraph 0052, (2018/11/03)

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.

3-phenyl-pyrones

-

, (2008/06/13)

Novel 3-phenyl-pyrones of the formula in which A, D, X and Y are each as defined in the description, a process for preparing these substances and their use as pesticides, fungicides and herbicides.

Arylphenyl-substituted cyclic keto enols

-

, (2008/06/13)

The present invention relates to novel arylphenyl-substituted cyclic ketoenols, their preparation and the use of such ketoenols as pesticides and/or herbicides. The novel arylphenyl-substituted cyclic ketoenols are of the formula (I) in which CKE refers to the cyclic ketoenol and W, X, Y and Z are as defined in the specification.

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