Enilconazole

Base Information

• Chemical Name: Enilconazole
• CAS No.: 35554-44-0
• Deprecated CAS: 51004-46-7,73790-28-0
• Molecular Formula: C14H14Cl2N2O
• Molecular Weight: 297.184
• Hs Code.: 29332900
• European Community (EC) Number: 252-615-0
• ICSC Number: 1303
• NSC Number: 759313
• UN Number: 2811,2902
• UNII: 6K0NOF3XQ6
• DSSTox Substance ID: DTXSID8024151
• Nikkaji Number: J21.235K
• Wikipedia: Enilconazole
• Wikidata: Q421576
• NCI Thesaurus Code: C81505
• RXCUI: 1442172
• Metabolomics Workbench ID: 45106
• ChEMBL ID: CHEMBL356918
• Mol file: 35554-44-0.mol

Synonyms:1H-imidazole, 1-(2-(2,4-dichlorophenyl)-2-(2-propen-1-yloxy)ethyl)-, sulfate (1:1);enilconazole;enilconazole sulfate;imazalil;imazalil mononitrate;imazalil phosphate;imazalil sulfate;imazalil sulfate (1:1);imazalil sulphate;R 23979

Chemical Property of Enilconazole

Chemical Property:

• Appearance/Colour: slightly yellow to brown solidified oil
• Vapor Pressure: 1.58 x l0-4 Pa (20 °C)
• Melting Point: 52.7 °C
• Refractive Index: 1.5680 (estimate)
• Boiling Point: 448.5 °C at 760 mmHg
• PKA: 6.53 (weak base)
• Flash Point: 225.1 °C
• PSA: 27.05000
• Density: 1.23 g/cm³
• LogP: 4.13380
• Storage Temp.: 2-8°C
• Water Solubility.: 0.018 g/100 mL
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 296.0483185
• Heavy Atom Count: 19
• Complexity: 291
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Imazalil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, N
• Hazard Codes: Xn,N
• Statements: 20/22-41-50/53
• Safety Statements: 26-39-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Fungicides
• Canonical SMILES: C=CCOC(CN1C=CN=C1)C2=C(C=C(C=C2)Cl)Cl
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying.
• Effects of Short Term Exposure: The substance is severely irritating to the eyes.
• Effects of Long Term Exposure: The substance may have effects on the liver. This may result in impaired functions and tissue lesions.
• Description: Imazalil (also known as Enilconazole) is a kind of topical mycotic agent that used for the treatment of fungi infections. It is primarily used for the treatment of fungi attracted to tubers of the crops, including Fusarium spp, Phoma spp, and Helminthosporum solani which reduces the crop quality. It can also be applied to citrus fruits. In addition, it can also be used for the treatment of Microsporum spp and Aspergillus spp infections occurring in the dogs, either as a single topic agent or being combined with oral administrated itraconazole or griseofulvin. The mechanism of action of Imazalil is through suppressing the biosynthesis pathway of ergosterol through blocking the demethylation process. Imazalil is an imidazole fungicide that inhibits ergosterol biosynthesis. Imazalil inhibits the growth of various fungi in vitro including P. italicum, A. niger, U. maydis, B. alii, and C. cucumerinum in a pH-dependent manner (MICs = 0.005-2 μg/ml at pH 7). It inhibits S. cerevisiae, but not rat liver microsomal, cytochrome P450 enzymes (CYPs; IC50s = 0.088 and 80 μM, respectively), as well as aromatase CYP19 from human placental microsomes (IC50 = 0.34 μM). Imazalil activates the murine pregnane X receptor (PXR) in a concentration-dependent manner in a cell-based reporter assay. It increases hepatic CYP3A11 and CYP2B10 mRNA levels in mice when administered at a dose of 100 mg/kg. Imazalil also increases Ki-67-positive nuclei in liver sections and hepatic MCM2 mRNA levels, markers of cell proliferation, in mice when co-administered with the murine constitutive androstane receptor (mCAR) agonist TCPOBOP . Formulations containing imazalil have been used to control fungal infection in agriculture.
• Uses: antifungal As a disinfectant for stable and kennel equipment; experimentaly as an agricultural fungicide. Imazalil is a systemic fungicide with protective and curative action. It is used for the control of a wide range of fungal diseases on fruit, vegetables and ornamentals, powdery mildew on roses and storage diseases of citrus fruit, pome fruit, bananas and seed potatoes. It is also used as a seed dressing, for control of diseases of cereals (particularly Fusarium and Helminthosporium spp.), and it is particularly active against benzimidazole-resistant strains of plant-pathogenic fungi.

Technology Process of Enilconazole

There total 5 articles about Enilconazole 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: 95.6%

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) + 3-chloroprop-1-ene (107-05-1) → 1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole (35554-44-0)

Guidance literature:

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol; With potassium hydroxide; In water; dimethyl sulfoxide; at 20 ℃; for 1h;

3-chloroprop-1-ene; In water; dimethyl sulfoxide; at 30 ℃; for 3h; Solvent; Temperature;

Reference yield: 64.4%

1H-imidazole (288-32-4) + 3-chloroprop-1-ene (107-05-1) + 2,2',4'-trichloroacetophenone (4252-78-2) → 1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole (35554-44-0)

Guidance literature:

2,2',4'-trichloroacetophenone; With tris(triphenylphosphine)ruthenium(II) chloride; acetic acid; triethylamine; at 70 ℃; for 9h;

1H-imidazole; With N,N-dimethyl acetamide; sodium hydroxide; at 50 - 100 ℃; for 5h;

3-chloroprop-1-ene; at 105 ℃; for 6h; Reagent/catalyst; Solvent;

Reference yield: 17.0%

allyl bromide (106-95-6) + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → 1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole (35554-44-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/S0223-5234(97)89644-4

upstream raw materials:

allyl bromide

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol

1H-imidazole

3-chloroprop-1-ene

Downstream raw materials:

1-[β-(Allyloxy)-2,4-dichlorophenethyl]-3-[N-(p-fluorophenyl)-carbamoylmethyl]imidazolium chloride

S-(+)-imazalil

R-(?)-imazalil

Refernces

• 1、 -. "Enilconazole bulk drug preparation method". Paragraph 0039-0055. . Retrieved 2019/11/20.
• 2、 Oh, Keimei,Murofushi, Noboru. "Design and synthesis of novel imidazole derivatives as potent inhibitors of allene oxide synthase(CYP74)". . p. 3707 - 3711. Retrieved 2007/10/03.