Bitertanol

Title: Bitertanol
CAS Registry Number: 55179-31-2
CAS Name: b-[(1,1¢-Biphenyl)-4-yloxy]-a-(1,1-dimethylethyl)-1H-1,2,4-triazol-1-ethanol
Additional Names: 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol; biloxazol
Manufacturers' Codes: BAY KWG 0599
Trademarks: Baycor (Bayer); Sibutol
Molecular Formula: C20H23N3O2
Molecular Weight: 337.42
Percent Composition: C 71.19%, H 6.87%, N 12.45%, O 9.48%
Literature References: Prepn: BE 814831; W. Kramer et al., US 3952002 (1974, 1976 both to Bayer AG). Physical properties and fungicidal activity: W. Brandes et al., Pflanzenschutz-Nachr. 32, 1 (1979). Mechanism of action: P. Kraus, ibid. 17; S. V. Overton et al., J. Hortic. Sci. 63, 183 (1988). GC determn in plants, soil and water: R. Brennecke, Pflanzenschutz-Nachr. 38, 33 (1985). Resolution of diastereomers: R. S. Burden et al., J. Chromatogr. 391, 273 (1987). In vitro activity: T. B. Sutton et al., Plant Dis. 69, 700 (1985). Field use in control of apple diseases: K. S. Yoder, ibid. 66, 580 (1982); W. F. S. Schwabe, Pflanzenschutz-Nachr. 35, 125 (1982); in wheat seed pretreatment: J. A. Hoffmann, D. V. Sisson, Plant Dis. 71, 839 (1987).
Properties: The marketed product is a mixture of diastereomers. Colorless crystals, mp 125-129°. Vapor pressure at 20°: 10-5mbar. Soly at 20° (g/100 g solvent): water 0.0005, ligroin (80-110°) 0-1, propan-2-ol 1-5, toluene 1-5, cyclohexane 5-10, methylene chloride 10-20. Stable in aqueous acid and alkaline solns. LD50 in rats, male and female mice (mg/kg): >5000, 4488, 4202 orally (Brandes).
Melting point: mp 125-129°
Toxicity data: LD50 in rats, male and female mice (mg/kg): >5000, 4488, 4202 orally (Brandes)
Use: Agricultural fungicide.
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