Chemical Properties
Colorless crystals. Melting point 75-93°C. Its nitrate salt has a melting point of 122°C. Solubility (g/kg) at 20°C: acetone 300, dichloromethane 700, methanol 400, isopropanol 100, toluene 250, water 0.08.
Uses
Etaconazol is a pesticide and fungicide.
Definition
ChEBI: A member of the class of dioxolanes that is 1,3-dioxolane substituted at position 2 by 2,4-dichlorophenyl and 1,2,4-triazol-1-ylmethyl groups and at position 4 by an ethyl group. An obsolete fungicide that was used to control powdery mildew on fruit and ot
er crops.
Production Methods
Etaconazole is commercially synthesised through a multi-step process involving the formation of a triazole-based fungicidal compound. The key reaction involves the condensation of a 1,2,4-triazole ring with a substituted dioxolane moiety, specifically 2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylmethyl. This intermediate is then linked to the triazole via a meth ylene bridge, forming the final active molecule: 1-[[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole. The synthesis requires precise control of stereochemistry, as etaconazole is a chiral compound with multiple isomers, and the 2S,4R-isomer exhibits the highest fungicidal activity.
Mechanism of action
Sterol biosynthesis inhibition
