Triadimefon

Base Information

• Chemical Name: Triadimefon
• CAS No.: 43121-43-3
• Deprecated CAS: 72650-40-9,93779-51-2,119143-30-5,148227-32-1,1135441-18-7,119143-30-5,93779-51-2
• Molecular Formula: C14H16ClN3O2
• Molecular Weight: 293.753
• Hs Code.: 2933990014
• European Community (EC) Number: 256-103-8
• NSC Number: 303303
• UN Number: 2765
• UNII: 1HW039CJF0
• DSSTox Substance ID: DTXSID3023897
• Nikkaji Number: J1.896A
• Wikipedia: Triadimefon
• Wikidata: Q2452254
• Metabolomics Workbench ID: 67730
• ChEMBL ID: CHEMBL520897
• Mol file: 43121-43-3.mol

Synonyms:1-(1,2,4-triazolyl)-1-(4-chlorophenoxy)-3,3-dimethylbutan-2-one;azocene;Bayleton;triadimefon;triadimefon nitrate;triadimefon sulfate;triadimenol;Tripinacloraz

Chemical Property of Triadimefon

Chemical Property:

• Appearance/Colour: Colorless to pale yellow crystalline solid with a slight odor
• Vapor Pressure: 5.26E-08mmHg at 25°C
• Melting Point: 82 °C
• Refractive Index: 1.579
• Boiling Point: 441.9 °C at 760 mmHg
• PKA: 1.41±0.11(Predicted)
• Flash Point: 221 °C
• PSA: 57.01000
• Density: 1.23 g/cm³
• LogP: 3.12430
• Storage Temp.: APPROX 4°C
• Water Solubility.: 0.026 g/100 mL
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 293.0931045
• Heavy Atom Count: 20
• Complexity: 338

Purity/Quality:

99% ^*data from raw suppliers

Triadimefon ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, N, T, F
• Hazard Codes: Xn,N,T,F
• Statements: 22-43-51/53-39/23/24/25-23/24/25-11
• Safety Statements: 24-37-61-45-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Fungicides
• Canonical SMILES: CC(C)(C)C(=O)C(N1C=NC=N1)OC2=CC=C(C=C2)Cl
• Recent ClinicalTrials: REACH Personal Mobility Device Testing
• Description: Triadimefon has been a widely used fungicide on crops and nonfood products since the early 1970s. The metabolite triadimenol is also active and is registered separately for use as seed treatment. Triadimenol has a broad regulatory toxicology database, but its toxicity is considered to be encompassed in that of triadimefon and therefore the same study was used by the United States Environmental Protection Agency (US EPA) in establishing regulatory levels for both pesticides. In nontarget species, dopaminergic neurotoxicity is the primary effect, but with chronic exposures its toxicities include hepatic, carcinogenic, developmental, and reproductive effects.
• Uses: Systemic fungicide used to control mildews and rusts that attack coffee, cereals, stone fruit, grapes and ornamentals. Triadimefon is used for the control of powdery mildews in cereals, pome fruit, stone fruit, berry fruit, vines, hops, cucurbits, tomatoes, vegetables, sugar beet, mangoes, ornamentals, turf, flowers, shrubs and trees, Monilinia spp. in stone fruit, black rot of grapes, leaf blotch, leaf spot and snow mould in cereals, pineapple disease butt rot in pineapples and sugar cane, leaf spots and flower blight in flowers, shrubs and trees and many other diseases of turf. antifungal, P450 inhibitor Triadimefon is an triazole fungicide is used for the management of mango powdery mildew in South Gujarat.

Technology Process of Triadimefon

There total 25 articles about Triadimefon 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: 94.7%

1-[3-(trifluoromethyl)phenyl]ethanone oxime (99705-50-7) + methyl (E)-2-[2-(bromomethyl)phenyl]-2-(methoxyimino)acetate (133409-72-0) → trifloxystrobin (43121-43-3,141517-21-7)

Guidance literature:

With sodium methylate; In N,N-dimethyl-formamide; at 20 ℃; for 0.00694444h; Solvent; Temperature; Flow reactor;

Reference yield: 94.5%

(E)-methyl 2-(2-(chloromethyl)phenyl)-2-(methoxyimino)acetate (189813-45-4) + 1-[3-(trifluoromethyl)phenyl]ethanone oxime (99705-50-7) → trifloxystrobin (43121-43-3,141517-21-7)

Guidance literature:

With sodium methylate; In N,N-dimethyl acetamide; at 30 ℃; for 0.00833333h; Solvent; Flow reactor;

Reference yield: 91.0%

(E)-methyl 2-(2-(chloromethyl)phenyl)-2-(methoxyimino)acetate (189813-45-4) + 1-[3-(trifluoromethyl)phenyl]ethanone oxime → trifloxystrobin (43121-43-3,141517-21-7)

Guidance literature:

1-[3-(trifluoromethyl)phenyl]ethanone oxime; With potassium hydroxide; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;

(E)-methyl 2-(2-(chloromethyl)phenyl)-2-(methoxyimino)acetate; In N,N-dimethyl-formamide; at 20 ℃; for 5h;

upstream raw materials:

4-Amino-1-[1-(4-chloro-phenoxy)-3,3-dimethyl-2-oxo-butyl]-4H-[1,2,4]triazol-1-ium; chloride

1,2,4-Triazole

1-(4-chlorophenoxy)-1-chloro-3,3-dimethyl-butan-2-one

(R)-1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one

Downstream raw materials:

1-(4-chloro-phenoxy)-2,3,3-trimethyl-1-[1,2,4]triazol-1-yl-butan-2-ol

copper(II) 2,3,4,5,6-pentachlorophenolate (3,3-dimethyl-1-(1-H-1,2,4-triazolyl-1)-1-(4-chlorophenoxy)butan-2-one)

copper(II) chloride (3,3-dimethyl-1-(1-H-1,2,4-triazolyl-1)-1-(4-chlorophenoxy)butan-2-one)

1-phenoxy-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone

Refernces

• 1、 -. "Method for preparing trifloxystrobin by adopting microchannel reactor". Paragraph 0051-0057; 0065-0071. . Retrieved 2021/09/04.
• 2、 -. "Preparation method of trifloxystrobin". Paragraph 0027-0037. . Retrieved 2020/07/12.