Triadimenol

Description

Triadimenol is a metabolite of triadimefon , a broad-spectrum chiral triazole fungicide, that is formed by reduction of a carbonyl group to the corresponding alcohol. It is teratogenic, inducing cranial nerve and ganglia abnormalities in a rat post-implantation whole embryo culture model when used at concentrations ranging from 12.5 to 125 μM. In vivo, triadimenol induces embryotoxicity in rats and rabbits when administered orally at doses of 100 and 40 mg/kg, respectively. Embryonic exposure to triadimenol (3-3,000 μg/L) induces embryonic mortality as well as decreases fertility and increases the number of female offspring in medaka fish (O. latipes).

The Uses of Triadimenol

Triadimenol is used for the control of powdery mildews, rusts and Rhynchosporium in cereals, and also as a seed treatment to control bunt, smut and other cereal diseases. It is also used on vines, hops, coffee, tomatoes, vegetables, fruit, tobacco, sugar cane, ornamentals and other crops, mainly against powdery mildews, rusts and various leaf spot diseases.

The Uses of Triadimenol

β-(4-Chlorophenoxy)-α-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol is a agricultural fungicide that is systemically active against powdery mildews and rusts of grains.

The Uses of Triadimenol

Systemic agricultural fungicide; cereal seed protectant.

What are the applications of Application

Triadimenol is a triazole-type anti-fungal demonstrating estrogen receptor agonism

Definition

ChEBI: A member of the class of triazoles that is 3,3-dimethyl-1-(1,2,4-triazol-1-yl)butane-1,2-diol substituted at position O1 by a 4-chlorophenyl group. A fungicide for cereals, beet and brassicas used to control a range of diseases including powdery mildew, ru ts, bunts and smuts.

Agricultural Uses

Fungicide: Triadimenol is used to control seed-and soil-borne diseases and to provide early season control of foliar diseases. It is applied to seeds of barley, corn, oats, rye, sorghum and wheat and also to fruits, vegetables and ornamentals. Registered for use in EU countries . Registered for use in the U.S. U.S. Maximum Allowable Residue Levels for Triadimenol

Trade name

BAYFIDAN®; BAYFRDAN EW®; BAY KWG 0519®; BAYTAN® SEED TREATMENT; BAYTAN 30® FUNGICIDE; PROTEGE ALLEGIANCE BAYTAN®; SPINNAKER®; SUMMIT®; TRIADIMENOL®; TRIAFOL®; TRIAPHOL®

Metabolic pathway

When triadimenol is irradiated by UV light in methanol solution, two major degradation products are identified as 1-(4-chlorophenoxy)-3,3-dimethylbutan-2-one and 1-phenoxy-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan- 2-ol. When a spray deposit on apple leaves is exposed outdoors to natural sunlight, the only product detected is the butanone metabolite. The butanone metabolite has very low fungicidal activity against apple powdery mildew, whereas the butanol metabolite gives some control of infection.

Degradation

When a methanolic solution of triadimenol (1) in borosilicate glass apparatus was irradiated by a medium pressure mercury lamp for 20 days, 50% of the triadimenol was photodegraded. The products identified were 1-(4-chlorophenoxy)-3,3-dimethyl^-1-(1H -1,2,4-triazol^-1-yl)butan-2- one (major product) (2), 4-chlorophenol (3) and 1-phenoxy-3,3-dimethyl- 1-(1H-1,2,4-triazol^-1-yl)butan-2-ol(4 ). When triadimenol was irradiated as a solid deposit, 55% of the parent compound was recovered after 18 days and the same products were identified. Losses may be accounted for by volatilisation or photodegradation (Clark and Watkins, 1986) (Scheme 1). The only major product detected 33 days after triadimenol had been applied to apple tree leaf surfaces exposed to light outdoors was 2.