Triflumizole

The Uses of Triflumizole

Triflumizole is used for the control of Gymnospurangum and Venturia spp. in pome fruit, against powdery Erysiphaceae in fruit and vegetables, and against Fusarium, Fulvia and Monilia spp. It is also used as a seed treatment against Helminthospurium, Tilletia and Ustilago spp. in cereals.

Definition

ChEBI: Triflumizole is a carboxamidine resulting from the formal condensation of the amino group of 4-chloro-2-(trifluoromethyl)aniline with the oxygen of the acetyl group of N-(propoxyacetyl)imidazole. A sterol demethylation inhibitor, it is used as a fungicide for the control of powdery mildew, scab and other diseases on a variety of crops. It has a role as an EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor and an antifungal agrochemical. It is a member of monochlorobenzenes, a member of imidazoles, a member of (trifluoromethyl)benzenes, a carboxamidine, an ether, a conazole fungicide and an imidazole fungicide.

Metabolic pathway

Triflumizole is unstable in aqueous solution when exposed to light and it is readily metabolised by plants and animals. The primary route of metabolism is by cleavage of the imidazole ring to give several metabolites which retain the 4-chloro-2-trifluoromethylaniline moiety. The major metabolite in crops, 2, is formed by loss of the imidazole ring.

Degradation

Aqueous solutions of triflumizole are degraded by sunlight with a DT₅₀ of 29 hours. The sole hydrolysis product of triflumizole in the dark is 2, which is formed by loss of the imidazole ring.
The major product of photolysis of triflumizole is 4, which is probably formed in the presence of oxygen via 3. This compound was soluble in the solid state but decomposed in solution, even if stored in a refrigerator (Hashimoto et al., 1990).