Description
Imibenconazole is a triazole fungicide. It has a low aqueous solubility, is slightly volatile and, based on its chemical properties, it is non-mobile and unlikely to leach to groundwater. It is not generally persistent in soil systems but may be moderately persistent in aquatic systems under certain conditions. It has a low mammalian toxicity. It shows a moderate level of toxicity to fish, daphnia and earthworms but is relatively non-toxic to honeybees, birds and algae.
Chemical Properties
The pure product is white crystals. mp 89.5-90°C, vapor pressure 0.85×10-4 Pa (25°C). Solubility: acetone 1063 g/L, benzene 580 g/L, xylene 250 g/L, methanol 120 g/L, water 1.79 g/L. Stable in weakly alkaline conditions and photostable, but unstable in strong acids and bases.
Uses
Imibenconazole is used to control scab, powdery mildew, Alternaria
leaf spot, sooty blotch, fly speck and rust on apples, scab and rust on
pears, scab and powdery mildew on fruits, and anthracnose and other
diseases on roses and chrysanthemums.
Definition
ChEBI: A member of the class of imidothioates that is the S-4-chlorobenzyl thioester of N-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanimidothioic acid. Used to control a range of fungal diseases affect
ng fruit, vegetables, turf and ornamentals. It has a low mammalian toxicity and shows a moderate level of toxicity to fish, daphnia and earthworms but is relatively non-toxic to honey bees, birds and algae.
Production Methods
Imibenconazole is commercially synthesised through a multi-step process involving triazole ring formation and chlorinated aromatic substitution. The production begins with the preparation of key intermediates including 1H-1,2,4-triazole and chlorinated phenyl derivatives. These are coupled through thioether and amidation reactions to form the final imibenconazole molecule, which features a complex structure with multiple halogen substitutions and a sulphur bridge. The synthesis is carried out under controlled temperature and pH conditions to ensure high yield and purity, followed by crystallisation.
Mechanism of action
Systemic with curative and preventative action. Inhibits germ tube and mycellium growth. Sterol biosynthesis inhibitor.
Metabolic pathway
There is little published information available on the metabolism of imibenconazole.
Based on the available data (PM) the reaction in Scheme 1 is
proposed.
Degradation
Imibenconazole is stable in weak alkali but it is unstable in acidic and in
strongly alkaline conditions (PM).
