Azoxystrobin

Base Information

• Chemical Name: Azoxystrobin
• CAS No.: 131860-33-8
• Deprecated CAS: 215934-32-0,296237-03-1,918881-33-1
• Molecular Formula: C22H17N3O5
• Molecular Weight: 403.394
• Hs Code.: 2933599014
• European Community (EC) Number: 603-524-3
• UNII: NYH7Y08IPM
• DSSTox Substance ID: DTXSID0032520
• Nikkaji Number: J588.357A
• Wikipedia: Azoxystrobin
• Wikidata: Q2013860
• Metabolomics Workbench ID: 56398
• ChEMBL ID: CHEMBL230001
• Mol file: 131860-33-8.mol

Synonyms:amistar;azoxy-strobin;azoxystrobin;ICIA 5504;ICIA-5504;ICIA5504;methyl (2E)-2-(2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl)-3-methoxyacrylate;quadris

Chemical Property of Azoxystrobin

Chemical Property:

• Appearance/Colour: white crystalline
• Vapor Pressure: 1.67E-13mmHg at 25°C
• Melting Point: 118 - 119oC
• Refractive Index: 1.626
• Boiling Point: 581.3 °C at 760 mmHg
• PKA: -0.93±0.18(Predicted)
• Flash Point: 305.3 °C
• PSA: 103.56000
• Density: 1.34 g/cm³
• LogP: 4.09318
• Storage Temp.: 0-6°C
• Water Solubility.: 6g/L at 20℃
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 403.11682065
• Heavy Atom Count: 30
• Complexity: 646

Purity/Quality:

99% ^*data from raw suppliers

Azoxystrobin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T;N,N,T
• Statements: 23-50/53
• Safety Statements: 22-45-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Fungicides
• Canonical SMILES: COC=C(C1=CC=CC=C1OC2=NC=NC(=C2)OC3=CC=CC=C3C#N)C(=O)OC
• Isomeric SMILES: CO/C=C(\C1=CC=CC=C1OC2=NC=NC(=C2)OC3=CC=CC=C3C#N)/C(=O)OC
• Description: Azoxystrobin is a second broad-spectrum strobilurin fungicide (28,29). It forms white solids with a mp = 116 ?C; vp = 1.1 × 10?7 mPa at 25 ?C; logP = 2.5 at 20?C; water solubility = 6 mg/L; and a half-life of 11 to 17 days for aqueous photolysis.
• Uses: Strobilurin fungicide; inhibits mitochondrial respiration by blocking electron transfer between cytochromes b and c1. Agricultural fungicide. Agricultural fungicide. Azoxystrobin has a very broad spectrum of activity and is active against fungal pathogens from all four taxonomic groups, the Oomycetes, Ascomycetes, Deuteromycetes and Basidiomycetes. It controls diseases on cereals, rice, vines, apples, peaches, bananas, citrus, curcurbits, potatoes, tomatoes, peanuts, coffee and turf.

Technology Process of Azoxystrobin

There total 52 articles about Azoxystrobin 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: 100.0%

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) + salicylonitrile (611-20-1) → azoxystrobin (215934-32-0,131860-33-8,143130-94-3)

Guidance literature:

With potassium carbonate; quinuclidine hydrochloride; In 4-methyl-2-pentanone; at 60 - 80 ℃; for 0.5h; Product distribution / selectivity;

Reference yield: 100.0%

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) → azoxystrobin (215934-32-0,131860-33-8,143130-94-3)

Guidance literature:

salicylonitrile; With potassium carbonate; 1,4-diaza-bicyclo[2.2.2]octane; In N,N-dimethyl-formamide; at 60 ℃; for 0.166667h;

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate; In N,N-dimethyl-formamide; at 60 - 84 ℃; for 0.333333h; Product distribution / selectivity;

Reference yield: 98.0%

salicylonitrile (611-20-1) → azoxystrobin (215934-32-0,131860-33-8,143130-94-3)

Guidance literature:

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate; With potassium carbonate; In N,N-dimethyl-formamide; at 60 ℃; for 0.0833333h;

salicylonitrile; In N,N-dimethyl-formamide; at 60 ℃; for 5h;

1,4-diaza-bicyclo[2.2.2]octane; In N,N-dimethyl-formamide; at 60 - 89 ℃; for 0.166667h; Product distribution / selectivity;

upstream raw materials:

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

salicylonitrile

1-methyl-pyrrolidin-2-one

ethylene glycol

Downstream raw materials:

methyl (E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yl]oxyphenyl]-3-methoxyprop-2-enoate

2-(6-hydroxypyrimidin-4-yloxy)benzonitrile

(E)-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylic acid

Refernces

• 1、 -. "Method for improving conversion rate of azoxystrobin". Paragraph 0066-0069. . Retrieved 2021/03/31.
• 2、 -. "PREPARATION METHOD FOR AZOXYSTROBIN AND INTERMEDIATE THEREOF". . . Retrieved 2021/01/25.