Description
Flusilazole is a curative and preventative fungicide used to control a range of fungal pathogens. It has a moderate aqueous solubility and a low volatility. It can be persistent in soils and water-sediment systems depending on local conditions. Risk of leaching to groundwater is low. There are concerns that flusilazole may be a reproduction / developmental toxin and an endocrine disrupter. Oral mammalian toxicity is moderate. For most species ecotoxicity is moderate.
Chemical Properties
Brown-red viscous liquid
Uses
Agricultural fungicide.
Uses
Flusilazole is a broad spectrum fungicide used to control fungal
disease caused by pathogens of the Ascomycetes, Basidiomycetes and
Deuteromycetes families. Flusilazole exhibits curative and preventative
activities and is recommended for use in agriculture, horticulture and
viticulture. Diseases controlled include eyespot, mildew, and rusts of
cereals, cercospora and rust of sugar beets, leaf spots of oilseed rape,
scab and mildew of pome and stone fruits, mildew and black rot of
grapes and Sigatoka disease of bananas.
Uses
Flusilazole is a silicon-containing triazole fungicide. Flusilazole is used to control fungal infections on a variety of fruit and vegetable crops
Definition
ChEBI: Flusilazole is an organosilicon compound that is dimethylsilane in which the hydrogens attached to the silicon are replaced by p-fluorophenyl groups and a hydrogen attached to one of the methyl groups is replaced by a 1H-1,2,4-triazol-1-yl group. It is a broad-sepctrum fungicide used to protect a variety of crops. It has a role as a xenobiotic, an environmental contaminant, an EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor and an antifungal agrochemical. It is a member of monofluorobenzenes, a member of triazoles, an organosilicon compound, a conazole fungicide and a triazole fungicide.
Production Methods
Flusilazole is commercially produced through a multi-step synthesis involving organosilicon and triazole chemistry. The process typically begins with the preparation of a triazole ring system, which is then functionalized with difluorophenyl groups and a trimethylsilyl moiety. Key reactions include nucleophilic substitution, condensation, and silylation, requiring precise control of temperature, solvents, and catalysts to ensure high yield and purity.
Mechanism of action
Broad-spectrum, systemic with protective and curative action. Sterol biosynthesis inhibitor.
Metabolic pathway
Flusilazole is stable to aqueous hydrolytic and photolytic degradation.
Although flusilazole is relatively stable in soil and is detected in plant and
animal samples, numerous degradation products have been reported. The
primary metabolic pathway involves the cleavage of the methylenesilicon
or/and methylene-triazole linkage. Another primary pathway
involves aryl hydroxylation followed by conjugation. The primary
metabolic/degradation pathways of flusilazole in soil, plant and animals
are presented in Scheme 1.
Degradation
Aqueous hydrolysis and photolysis are not sigruficant degradation pathways
for flusilazole (1). Flusilazole was stable (<5% decomposition) in
sterile buffers at pH 5, 7 and 9 (25 °C) for 34 days (Cadwgan, 1983). No
significant degradation was observed when fusilazole was irradiated with
simulated sunlight for 30 days at 300-450 nm in sterile buffer solution at
pH 7 (Carter, 1986).
