Azaconazole

Originator

Azaconazole,Chemical

The Uses of Azaconazole

Azaconazole is particularly active against wood-destroying and sapstain fungi. It is also used as a disinfectant in mushroom cultivation and on storage boxes for fruit and vegetables.

The Uses of Azaconazole

Fungicide for cultivation on wood; preservative for composite wood products.

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. A fungicide used mainly in ornamental crops to control canker and other diseases. Azaconazole is moderately toxic to mammals but is not expected to bioaccumulate. It is moderately toxic to birds, fish and aquatic invertebrates.

Manufacturing Process

A stirred and cooled (0°C) solution of 1-(2,4-diaminophenyl)-1-ethanone in a concentrated hydrochloric acid solution, water and acetic acid was diazotated with a solution of sodium nitrite in water. After stirring at 0°C, the whole was poured onto a solution of copper (I) chloride in a concentrated hydrochloric acid solution while stirring. The mixture was heated at 60°C. After cooling to room temperature, the product was extracted twice with 2,2'-oxybispropane. The combined extracts were washed successively with water, a diluted sodium hydroxide solution and again twice with water, dried, filtered and evaporated, yielding 1-(2,4-dichlorophenyl)-1-ethanone.
1-(2,4-Dichlorophenyl)-1-ethanon were dissolved in 1,2-ethanediol at heating. While stirring bromine were added dropwise, without external heating. After stirring at room temperature, 4-methylbenzenesulfonic acid and benzene were added. The whole was stirred and refluxed overnight with water-separator. The reaction mixture was evaporated and the residue was taken up in 2,2'- oxybispropane. The resulting solution was washed successively once with a dilute sodium hydroxide solution and 3 times with water, dried, filtered and evaporated. The residue was distilled, yielding 2-(bromomethyl)-2-(2,4- dichlorophenyl)-1,3-dioxolane.
6.9 parts of 1H-1,2,4-triazole in 150 parts of dimethylformamide were added to a stirred solution of 2.3 parts of sodium in 120 parts of methanol. The methanol was removed at normal pressure until the internal temperature of 130°C was reached. Then, 25 parts of 2-(bromomethyl)-2-(2,4- dichlorophenyl)-1,3-dioxolane were added. The reaction-mixture was stirred and refluxed for 3 h. It was allowed to cool to room temperature and poured onto water. The precipitated product was filtered off, yielding 12 parts of 1-[2- (2,4-dichlorophenyl)-1,3-dioxolan-2-yl-methyl]-1H-1,2,4-triazole, melting point 109.9°C (crystallized from diisopropylether, activated charcoal).

Therapeutic Function

Antifungal

Metabolic pathway

Little published dormation is available on the metabolism of azaconazole.

Degradation

Azaconazole is stable to light under normal storage conditions (but not in ketonic solvents). It is stable at temperatures up to 220 °C.