2771. Cyproconazole

Nomenclature

CAS number: 94361-06-5
α-(4-Chlorophenyl)-α-(1-cyclopropylethyl)-1H-1,2,4-triazole-1-ethanol; (2RS,3RS)-2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol; SAN-619F; SN-108266; Alto (Syngenta); Atemi (Syngenta); Bonanza (Novartis Agro); Paindor (Novartis Agro); Sentinel (Syngenta).
C15H18ClN3O; mol wt 291.78.
C 61.75%, H 6.22%, Cl 12.15%, N 14.40%, O 5.48%.

Description and references

Broad spectrum triazole antifungal; sterol demethylase inhibitor. Prepn: F. Schaub, DE 3406993; idem, US 4664696 (1984, 1987 both to Sandoz). Mode of action: M. S. Fuller et al., Pestic. Biochem. Physiol. 36, 115 (1990). Synergism with herbicides: H. R. Kataria, U. Gisi, Crop Prot. 9, 403 (1990). Field trials in winter wheat: J. P. Devey et al., Brighton Crop Prot. Conf. - Pests Dis. 1990, 801; in cereals in combination with prochloraz, q.v.: R. I. Harris et al., ibid. 813. Review: U. Gisi et al., Proc. Br. Crop Prot. Conf. - Pests Dis. 1986, 33-40.

Chemical structure

Properties

Colorless crystals from hexane/CH2Cl2, mp 103-105°. Soly at 25° (%w/w): water 0.0140 ±0.0004; acetone >23; ethanol >23; xylene 12; DMSO >18. Vapor pressure at 20°: 2.6 × 10-7 torr. LD50 in male and female rats (mg/kg): 1020, 1330 orally; in rats: 2000 dermally. LD50 in carp: 18.9 mg/l; in trout 7.2 mg/l; in bluegill sunfish 6.0 mg/l in water. LD50 in bobwhite quail (mg/kg): 150 orally; LD50 (8 day dietary) in bobwhite quail, mallard duck: 816, 1197 mg/kg (Gisi, 1986).

Derivative

Combination with prochloraz.

Nomenclature

Sportak Delta (Aventis CropSci.); Tiptor (Syngenta); Epicure (Novartis Agro).

Use

Agricultural fungicide.