9593. Triadimenol

Nomenclature

CAS number: 55219-65-3
β-(4-Chlorophenoxy)-α-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol; 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol; BAY KWG 0519; Bayfidan (Bayer); Baytan (Bayer); Spinnaker (Shell); Summit (Mobay).
C14H18ClN3O2; mol wt 295.76.
C 56.85%, H 6.13%, Cl 11.99%, N 14.21%, O 10.82%.

Description and references

Agricultural fungicide systemically active against powdery mildews and rusts of grains. Commercial product is mixture of 2 diastereoisomers. Prepn: BE 814831; W. Kramer et al., US 3952002 (1974, 1976 both to Bayer AG). Comprehensive description: P. E. Frohberger, Pflanzenschutz-Nachr. 31, 11 (1978). Field trials in cereal diseases: J. Trgner-Born, T. van den Boom, ibid. 25. Inhibits fungal ergosterol biosynthesis: H. Buchenauer, Pestic. Sci. 9, 507 (1978). Active fungal metabolite of triadimefon, q.v.: M. Gasztonyi, ibid. 12, 433 (1981). GC separation of enantiomers: T. Clark, A. H. B. Deas, J. Chromatogr. 329, 181 (1985).

Chemical structure

Properties

Crystals, mp 112-117°. Slight, non-specific odor. Soly in water at 20°: 0.012 g/100 g. Soluble in alcohol, ketones. LD50 in male, female rats (mg/kg): 1161, 1105 orally; >5000 dermally, 24-hr; LD50 in quail: >10000 mg/kg (Frohberger).

Use

Systemic agricultural fungicide; cereal seed protectant.