Imazalil

Imazalil Basic information
Description References
Product Name:Imazalil
Synonyms:rac-1-[(R*)-2-(Allyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole;Imazalil base;Imazalil 100mg [35554-44-0];Imazalil Solution, 100ppm;(.+/-.)-1-(beta-(Allyloxy)-2,4-dichlorophenethyl)imidazole;deccozils75;Eniloconazol;eniloconazol(sp)
CAS:35554-44-0
MF:C14H14Cl2N2O
MW:297.18
EINECS:252-615-0
Product Categories:API;CLINAFARM;FUNGICIDE;35554-44-0
Mol File:35554-44-0.mol
Imazalil Structure
Imazalil Chemical Properties
Melting point 52.7°C
Boiling point >340°C
density 1.348
vapor pressure 1.58 x l0-4 Pa (20 °C)
refractive index 1.5680 (estimate)
storage temp. 2-8°C
solubility Chloroform: Slightly Soluble; Methanol: Slightly Soluble
pka6.53 (weak base)
form neat
Water Solubility 0.018 g/100 mL
Merck 13,3616
BRN 545683
InChIKeyPZBPKYOVPCNPJY-UHFFFAOYSA-N
LogP3.820
CAS DataBase Reference35554-44-0(CAS DataBase Reference)
NIST Chemistry ReferenceImazalil(35554-44-0)
EPA Substance Registry SystemImazalil (35554-44-0)
Safety Information
Hazard Codes Xn,N
Risk Statements 20/22-41-50/53
Safety Statements 26-39-60-61
RIDADR 2588
WGK Germany 3
RTECS NI4776000
HazardClass 6.1(b)
PackingGroup III
HS Code 29332900
Hazardous Substances Data35554-44-0(Hazardous Substances Data)
MSDS Information
Imazalil Usage And Synthesis
DescriptionImazalil (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. 
Referenceshttp://www.vetbook.org/wiki/dog/index.php?title=Enilconazole
https://en.wikipedia.org/wiki/Enilconazole
https://www.mysciencework.com/publication/show/f0382c741754e9200388abe8cf2f0133

Description
DescriptionImazalil 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.
Usesantifungal
UsesAs a disinfectant for stable and kennel equipment; experimentaly as an agricultural fungicide.
UsesImazalil 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.
DefinitionChEBI: 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole is a member of the class of imidazoles in which the hydrogen at position 1 is replaced by a 2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl group. It is a member of imidazoles, an ether and a dichlorobenzene.
General DescriptionSlightly yellow to brown solidified oil. Non-corrosive. Used as a fungicide.
Air & Water ReactionsWater soluble.
Reactivity ProfileImazalil is an imidazole derivative.
Safety ProfilePoison by ingestion and intraperitoneal routes. Experimental reproductive effects. A skin and eye irritant. When heated to decomposition it emits toxic fumes of Cland NOx.
Veterinary Drugs and TreatmentsAlthough no dosage forms are currently commercially available for topical use in the USA, Enilconazole is used topically for treating dermatophytosis in small animals and horses using compounded products. A commercially available topical rinse Imaverol? (Janssen) 10% is available with canine, bovine and equine use labeling in many countries. Intranasal instillation of enilconazole after plaque debridement has also been shown useful in treating nasal aspergillosis in small animals.
Use of topical enilconazole on cats with dermatophytosis is somewhat controversial as there are apparently no products with feline labeling available in Europe or Canada. There are preliminary reports of safely and successfully using enilconazole on dermatophytic cats in combination with oral itraconazole.
A topical product and a poultry environmental disinfectant product (Clinafarm EC?) is available in the USA. It is technically illegal to use this product other than it is labeled; it is an EPA licensed product in the USA.

Metabolic pathwayPublished information is available on the metabolism of imazalil in plants and soils. The principal metabolite in plants and soils is 1-[2-(2,4- dichlorophenyl)-2-hydroxyethyl]-1H-imidazole.
DegradationImazalil is very stable to hydrolysis in dilute acids and alkalis at room temperature, in the absence of light. It is also stable to light under normal storage conditions.
Ethanol Levamisole Phenylacetone Ethylbenzene Ethylparaben Dichloromethylphenylsilane Ethyl cellulose Hydroxyethyl Cellulose Hydroxyethyl starch Imidazole Ethyl maltol Diethyl ether Ethyl acetate Vinylimidazole Ethyl acrylate Dichloroethane Chlorphenamine maleate Phenylhydrazine

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