Hexaconazole

Base Information

• Chemical Name: Hexaconazole
• CAS No.: 79983-71-4
• Deprecated CAS: 103556-63-4,87677-54-1,205862-67-5
• Molecular Formula: C14H17Cl2N3O
• Molecular Weight: 314.214
• Hs Code.: 2933990014
• European Community (EC) Number: 413-050-7,616-763-3
• UNII: SX9R3X1FQV
• DSSTox Substance ID: DTXSID4034653
• Wikipedia: Hexaconazole
• Wikidata: Q424794
• ChEMBL ID: CHEMBL1898860
• Mol file: 79983-71-4.mol

Synonyms:hexaconazole

Chemical Property of Hexaconazole

Chemical Property:

• Vapor Pressure: 1.99E-10mmHg at 25°C
• Melting Point: 111 °C
• Refractive Index: 1.597
• Boiling Point: 490.3 °C at 760 mmHg
• PKA: 12.26±0.29(Predicted)
• Flash Point: 250.3 °C
• PSA: 50.94000
• Density: 1.3 g/cm³
• LogP: 3.66290
• Storage Temp.: 0-6°C
• Water Solubility.: 17 mg l-1(20 °C)
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 313.0748676
• Heavy Atom Count: 20
• Complexity: 308

Purity/Quality:

99% ^*data from raw suppliers

Hexaconazol PESTANAL ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, N
• Hazard Codes: Xn;N,N,Xn
• Statements: 22-43-51/53
• Safety Statements: 2-24-37-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC(CN1C=NC=N1)(C2=C(C=C(C=C2)Cl)Cl)O
• Description: Hexaconazole is a kind of broad-spectrum systemic trazole fungicide. It can be used for the treatment of many kind of fungi diseases caused by ascomycetes, basidiomycetes, and imperfect fungi. It is especially suitable for the treatment of fungi diseases such as powdery mildew, rust, scab, brown blotch and anthracnose caused by ascomycetes and basidiomycetes. In China, India and some other Asian countries, it is mainly used for the control of rice sheath blight. It is applicable to apples, grapes, bananas, vegetables, peanuts, and cereal crops as well as ornament plants. Its mechanism of action is through inhibiting the biosynthesis of ergosterol (a key component of the fungi membrane) of fungi. Hexaconazole is a broad-spectrum triazole fungicide that inhibits ergosterol biosynthesis via inhibition of the cytochrome P450-dependent 14α-demethylation of lanosterol, which results in disruption of the fungal cell membrane and cell death. It is fungicidal against the powdery mildews B. graminis and S. cucurbitae on cucumber plants in a concentration-dependent manner and is curative against powdery mildew on barley plants when used at a concentration of 6.7 mg/L. It also inhibits growth of R. bataticola and S. rolfsii (ED50s = 6.35 and 1.27 mg/L, respectively). Exogenous application of hexaconazole (15 mg/L) to M. chamomilla plants improves water, proline, and protein contents as well as increases non-enzymatic and enzymatic antioxidant and apigenin-7-glucoside content during a water deficit stress tolerance test. Hexaconazole inhibits the differentiation of mouse embryonic stem cells into cardiomyocytes (EC50 = 16.6 μM). It also induces bone morphological defects in mouse fetuses when administered to pregnant adult females during gestation.
• Uses: Hexaconazole is a systematic fungicide of the triazole class. Hexaconazole has a broad spectrum antifungal activity and is commonly used in the control of apple, coffee and peanut diseases. Agricultural fungicide. Hexaconazole is a systemic fungicide used for the control of many fungi, particularly Ascomycetes and Basidiomycetes on a variety of crops. It controls powdery mildews, scabs and rusts of vines, pome fruits, vegetables and major diseases of small grain cereals.

Technology Process of Hexaconazole

There total 4 articles about Hexaconazole 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: 12.0%

n-butyl magnesium bromide (693-03-8) + 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (58905-16-1) → hexaconazole (79983-71-4)

Guidance literature:

1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone; With magnesium bromide ethyl etherate; In dichloromethane; at 20 ℃; for 1.5h; Inert atmosphere;

n-butyl magnesium bromide; In diethyl ether; dichloromethane; at 0 - 20 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.ejmech.2017.03.075

Reference yield: 12.0%

→ hexaconazole (79983-71-4)

Guidance literature:

With magnesium bromide ethyl etherate; In dichloromethane;

Reference yield:

1-(2,4-dichlorophenyl)-2-(4-amino-4H-1,2,4-triazoliumyl)ethanone chloride (118227-30-8) → hexaconazole (79983-71-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogenchloride; sodium nitrite / water / 1 h / 0 - 20 °C

2.1: magnesium bromide ethyl etherate / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

2.2: 12 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; magnesium bromide ethyl etherate; sodium nitrite; In dichloromethane; water;

DOI:10.1016/j.ejmech.2017.03.075

upstream raw materials:

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

n-butyl magnesium bromide

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

2,2',4'-trichloroacetophenone

Downstream raw materials:

(R)-(+)-α-butyl-α-(2,4-dichlorophenyl)-1,2,4-triazole-1-ethanol

(S)-(-)-α-butyl-α-(2,4-dichlorophenyl)-1,2,4-triazole-1-ethanol

Refernces

• 1、 Shrestha, Sanjib K.,Garzan, Atefeh,Garneau-Tsodikova, Sylvie. "Novel alkylated azoles as potent antifungals". . p. 309 - 318. Retrieved 2017/04/11.
• 2、 -. "Synergistic Fungidical Active Substance Combinations". . . Retrieved 2008/12/04.