Triadimenol

Base Information

• Chemical Name: Triadimenol
• CAS No.: 55219-65-3
• Deprecated CAS: 131733-77-2
• Molecular Formula: C₁₄H₁₈ClN₃O₂
• Molecular Weight: 295.769
• Hs Code.: 29339900
• European Community (EC) Number: 259-537-6
• UNII: NFR7MRD9NM
• DSSTox Substance ID: DTXSID0032493
• Nikkaji Number: J11.445F
• Wikidata: Q15632882
• Pharos Ligand ID: 1B6U6GX7PM6P
• Metabolomics Workbench ID: 67741
• ChEMBL ID: CHEMBL520275
• Mol file: 55219-65-3.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 Triadimenol

Chemical Property:

• Appearance/Colour: powder
• Vapor Pressure: 1.84E-09mmHg at 25°C
• Melting Point: 110ºC
• Refractive Index: 1.579
• Boiling Point: 465.4 °C at 760 mmHg
• PKA: 13.29±0.20(Predicted)
• Flash Point: 235.3 °C
• PSA: 60.17000
• Density: 1.24 g/cm³
• LogP: 2.91610
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: A 62 mg l-1 (20 °C); B 33 mg l-1(20 °C)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 295.1087545
• Heavy Atom Count: 20
• Complexity: 303

Purity/Quality:

99.9% ^*data from raw suppliers

β-(4-Chlorophenoxy)-α-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol(MixtureofDiastereomers)(Triadimenol) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, F, T
• Hazard Codes: Xn,F,T
• Statements: 22-52/53-36-20/21/22-11-23-20/22
• Safety Statements: 22-61-36-26-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Fungicides
• Canonical SMILES: CC(C)(C)C(C(N1C=NC=N1)OC2=CC=C(C=C2)Cl)O
• Uses: It is a systemic broad-spectrum seed treatment fungicide which can kill pathogens attached to the internal and external surface of seed. It works through the inhibition of fungal ergosterol biosynthesis. It’s used on cereal grains to control powdery mildew and smut diseases such as loose smut, stinking smut and root rot on wheat, loose smut, rust, leaf stripe disease and net blotch etc on barley, and it is more than 90% effective when 100kg of seeds are treated with 30 ~ 50g of 25% DS. It is more than 90% effective when 100kg of seeds are treated with 42 ~ 75g of 25% DS to control smut on corn and sorghum head smut. If 100kg of seeds are treated with 30g of triadimenol and 5g of furidazol, it will be 92% to 100% effective for the control of loose smut, stripe disease, net blotch and root rot on spring barley , loose smut, stinking smut, snow mold on winter wheat, and leaf stripe disease, loose smut on spring oat. Triadimenol is a broad-spectrum fungicide with high efficiency and low toxicity. It is used on wheat and rice to control rust, powdery mildew, sheath blight and other diseases, and has a significant yield increasing effect. It can be also used as a cereal seed treatment and for the control of cereal smut. Systemic agricultural fungicide; cereal seed protectant. β-(4-Chlorophenoxy)-α-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol is a agricultural fungicide that is systemically active against powdery mildews and rusts of grains. Triadimenol is used for the control of powdery mildews, rusts and Rhynchosporium in cereals, and also as a seed treatment to control bunt, smut and other cereal diseases. It is also used on vines, hops, coffee, tomatoes, vegetables, fruit, tobacco, sugar cane, ornamentals and other crops, mainly against powdery mildews, rusts and various leaf spot diseases.
• Description: Triadimenol is a metabolite of triadimefon , a broad-spectrum chiral triazole fungicide, that is formed by reduction of a carbonyl group to the corresponding alcohol. It is teratogenic, inducing cranial nerve and ganglia abnormalities in a rat post-implantation whole embryo culture model when used at concentrations ranging from 12.5 to 125 μM. In vivo, triadimenol induces embryotoxicity in rats and rabbits when administered orally at doses of 100 and 40 mg/kg, respectively. Embryonic exposure to triadimenol (3-3,000 μg/L) induces embryonic mortality as well as decreases fertility and increases the number of female offspring in medaka fish (O. latipes).

Technology Process of Triadimenol

There total 5 articles about Triadimenol 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:

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one (43121-43-3) → 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (55219-65-3,70585-35-2,70585-37-4,82200-72-4,89482-17-7,89497-63-2,89497-64-3,89497-65-4,89497-66-5)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; for 1h; Ambient temperature;

Reference yield:

trans-3-tert-Butyl-2-(1,2,4-triazol-1-yl)-oxirane + sodium 4-chlorophenolate (1193-00-6) → 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (55219-65-3,70585-35-2,70585-37-4,82200-72-4,89482-17-7,89497-63-2,89497-64-3,89497-65-4,89497-66-5)

Guidance literature:

In methanol; ethyl acetate;

Reference yield:

sulfuric acid (7664-93-9) + aluminum isopropoxide (555-31-7) + 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one (43121-43-3) → 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (55219-65-3,70585-35-2,70585-37-4,82200-72-4,89482-17-7,89497-63-2,89497-64-3,89497-65-4,89497-66-5)

Guidance literature:

In water; isopropyl alcohol;

upstream raw materials:

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

sodium 4-chlorophenolate

sulfuric acid

aluminum isopropoxide

Downstream raw materials:

Toluene-4-sulfonic acid (S)-1-[(S)-(4-chloro-phenoxy)-[1,2,4]triazol-1-yl-methyl]-2,2-dimethyl-propyl ester

Toluene-4-sulfonic acid (S)-1-[(R)-(4-chloro-phenoxy)-[1,2,4]triazol-1-yl-methyl]-2,2-dimethyl-propyl ester

1-(4-chlorophenoxy)-3,3-dimethyl-2-[N-(2,3-dihydro-2,2-dimethyl-benzofuran-7-oxy-carbonyl)methylcarbamoyloxy]-1-(1,2,4-triazol-1-yl)butane

copper(II) 2,4,5-trichlorophenolate (3,3-dimethyl-1-(1-H-1,2,4-triazolyl-1)-1-(4-chlorophenoxy)butan-2-ol)

Refernces

• 1、 -. "Synergistic Combinations Of Active Ingredients". . . Retrieved 2012/02/15.
• 2、 -. "Synergistic Fungidical Active Substance Combinations". . . Retrieved 2008/12/04.