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HomeProduct name listImazalil

Imazalil

Synonym(s):1-[2-(Allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole;Imazalil

  • CAS NO.:35554-44-0
  • Empirical Formula: C14H14Cl2N2O
  • Molecular Weight: 297.18
  • MDL number: MFCD00055331
  • EINECS: 252-615-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-05 19:05:58
Imazalil Structural

What is Imazalil?

Description

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.

Description


The Uses of Imazalil

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.

The Uses of Imazalil

antifungal

The Uses of Imazalil

As a disinfectant for stable and kennel equipment; experimentaly as an agricultural fungicide.

What are the applications of Application

Imazalil is an antifungal agent that may have carcinogenic potential

Definition

ChEBI: 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 Description

Slightly yellow to brown solidified oil. Non-corrosive. Used as a fungicide.

Air & Water Reactions

Water soluble.

Reactivity Profile

Imazalil is an imidazole derivative.

Safety Profile

Poison 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 Treatments

Although 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 pathway

Published 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.

Degradation

Imazalil 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.

Properties of Imazalil

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
pka 6.53 (weak base)
form  neat
form  Solid
color  Light yellow to yellow
Water Solubility  0.018 g/100 mL
Merck  13,3616
BRN  545683
CAS DataBase Reference 35554-44-0(CAS DataBase Reference)
NIST Chemistry Reference Imazalil(35554-44-0)
EPA Substance Registry System Imazalil (35554-44-0)

Safety information for Imazalil

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
ghs
Skull and Crossbones
Acute Toxicity
GHS06
ghs
Environment
GHS09
GHS Hazard Statements H301:Acute toxicity,oral
H318:Serious eye damage/eye irritation
H332:Acute toxicity,inhalation
H410:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P273:Avoid release to the environment.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Imazalil

InChIKey PZBPKYOVPCNPJY-UHFFFAOYSA-N

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