General Description
Slightly yellow to brown solidified oil. Non-corrosive. Used as a fungicide.
Reactivity Profile
IMAZALIL(35554-44-0) is an imidazole derivative.
Air & Water Reactions
Water soluble.
Uses
As a disinfectant for stable and kennel equipment; experimentaly as an agricultural fungicide.
Uses
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.
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.
Mechanism of action
Systemic with curative and protective properties. Disrupts membrane function.
Synthesis
This embodiment provides a method for preparing 1-(2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole comprising the steps of: to a 500 mL three-necked flask under stirring conditions were added sequentially 185 g (4.0 mol) of formic acid, 45.1 g (0.2 mol) of 2,4-dichloro-2'-chloroacetophenone, 10 g of triethylamine ( 0.1 mol) and RuCl2(PPh3)3 5 g (0.01 mol). The mixture was heated to 70°C and kept reacting for 9 hours. After completion of the reaction, it was cooled to 50°C and subjected to reduced pressure distillation until no liquid dripped out, followed by cooling to room temperature. Sodium hydroxide 16 g (0.4 mol) and imidazole 22 g (0.32 mol) were added to the reaction mixture, heated to 100°C and kept reacting for 5 hours, then cooled to room temperature. 3-Chloropropene 24 g (0.32 mol) was added dropwise, heated to 105°C and kept the reaction for 6 hours. After the reaction was completed, it was cooled to room temperature, 320 mL of water was added and the crude product was obtained by filtration. The crude product was dissolved in 100 mL of ethanol, heated and refluxed for 1 h, then filtered at room temperature to obtain the pure product 1-(2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole 28.7 g, yield 64.4%, purity ≥ 98% by liquid phase analysis, melting point 50.9-52.0 °C.
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.
Pesticide Type
Fungicide; Veterinary substance
