9193. Tetraconazole

Nomenclature

CAS number: 112281-77-3
1-[2-(2,4-Dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]-1H-1,2,4-triazole; (RS)-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propyl 1,1,2,2-tetrafluoroethyl ether; M-14360; Domark (Isagro); Eminent (Isagro); Lospel (Isagro).
C13H11Cl2F4N3O; mol wt 372.15.
C 41.96%, H 2.98%, Cl 19.05%, F 20.42%, N 11.29%, O 4.30%.

Description and references

Systemic triazole antifungal; inhibitor of sterol biosynthesis. Prepn: JP Kokai 87 169773; R. Colle et al., US 5081141 (1987, 1992 both to Montedison). Chemical and biological properties: C. Garavaglia et al., Brighton Crop Prot. Conf. - Pests Dis. 1988, 49. Chemoenzymatic stereospecific synthesis and biological activity of racemate and enantiomers: D. Bianchi et al., J. Agric. Food Chem. 39, 197 (1991); stereoselective inhibition of ergosterol biosynthesis: F. Gozzo et al., Pestic. Biochem. Physiol. 53, 10 (1995). ELISA of commercial prepns: F. Forlani et al., J. Agric. Food Chem. 40, 328 (1992). Field trial on wheat: D. Pancaldi, I. Alberti, Informat. Fitopatolog. 44, 48 (1994).

Chemical structure

Properties

Viscous colorless oil. Vapor pressure (20°): 1.2× 10-5 mmHg. Log P (octan-1-ol/water): 3.1 (pH 7). Stable in dil. aq. soln at pH 5-9. Stable in sunlight. Soly (20°) mg/l: water 150. Readily sol in dichloromethane, acetone and methanol. LD50 orally in rats: 1150 mg/kg (Garavaglia).

Use

Agricultural fungicide.