Triadimenol

Synonyms

(1RS,2RS,1RS,2SR)-1-(4-Chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (IUPAC); 1-(4-Chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol; 2-(4-Chlorophenoxy)-1-tert-butyl-2-(1H-1,2,4-triazole-1-yl)ethanol; Bay KWG 0519; Bayfidan; Bayfidan EW; Baytan; Baytan 15; Baytan TF 3479B; KWG 0519; Spinnaker; Summit; Triafol; Triaphol; Tridan Fungicide; UK 199; beta-(4-Chlorophenoxy)-alpha-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol; 1H-1,2,4-Triazole-1-ethanol, beta-(4-chlorophenoxy)-alpha-(1,1-dimethylethyl)-; Ethanol, 2-(4-chlorophenoxy)-1-tert-butyl-2-(1H-1,2,4-triazole-1-yl)-; alpha-tert-Butyl-beta-(4-chlorophenoxy)-1H-1,2,4-triazole-1-ethanol; [ChemIDplus]

Category

Fungicides

Description

Solid with a mild non-specific odor; [Merck Index] Formulated as emulsifiable, soluble, and flowable concentrates and wettable powder; [Reference #1]

Sources/Uses

Used as an agricultural fungicide and seed protectant; [Merck Index] The major metabolite of the triazole fungicide triadimefon; A broad spectrum systemic fungicide used as seed treatment for barley, corn, cotton, oats, rye, sorghum, and wheat; An import tolerance is also set for bananas; [Reference #1] Used as fungicide for table and wine grapes, cereals, and cereal seed treatment in the EU; [EFSA]

Comments

Commercial material is mixture of two diastereoisomers; [Merck Index] Increased liver enzyme activity (ALT and AST) and histopathological liver changes observed in 13-week feeding study of rats at the three highest doses tested (500, 1,500, and 4,500 ppm); A 15-day dermal study of rabbits produced a NOAEL greater than highest tested dose (250 mg/kg/day); Teratogenic effects seen in tadpoles (branchial arches) and cultured rat embryos (cranial nerve and ganglia); No evidence of mutagenicity; [HSDB] Not irritating to skin or eyes of rabbits; Not sensitizing to guinea pig skin; No adverse effects to reproductive performance observed in 2-generation study of rats; No evidence of primary embryotoxic or teratogenic effects in rats or rabbits administered by gavage in the most sensitive stage of gestation; No evidence of carcinogenicity in rats or mice; [IUCLID] Repeated dose studies have shown the liver to be the target organ of toxicity (enlargement with corresponding changes in clinical chemistry); Chronic studies of rats and mice also demonstrated hepatotoxicity; Multigenerational studies produced reduced pup survival during lactation and decreased fertility index in all generations in one study; Acute triadimefon (structurally and metabolically similar fungicide) neurotoxicity studies of rats showed reversible hyperactivity and increased motor and locomotor activity without neuropathological changes; Sub-chronic studies produced consistent effects with no increase in severity observed; Does not possess potential for mutagenicity or carcinogenicity; [EFSA] See "Triadimefon."

Reference Link #1

Biomedical References

3.1E-10 mm Hg

LC50 (rat) = 2,580 mg/m3

Hepatoxic (a) from occupational exposure (secondary effect) or (b) in animal studies or in humans after ingestion

Processes

Industrial Processes with risk of exposure:

• Farming (Pesticides)