3629. Epoxiconazole

Nomenclature

CAS number: 133855-98-8; 106325-08-0 (unspecified stereo)
rel-1-[[(2R,3S)-3-(2-Chlorophenyl)-2-(4-fluorophenyl)oxiranyl]methyl]-1H-1,2,4-triazole; (2RS,3RS)-1-[3-(2-chlorophenyl)-2,3-epoxy-2-(4-fluorophenyl)-propyl]-1H-1,2,4-triazole; BAS-480-F; Opus (BASF).
C17H13ClFN3O; mol wt 329.76.
C 61.92%, H 3.97%, Cl 10.75%, F 5.76%, N 12.74%, O 4.85%.

Description and references

Ergosterol biosynthesis inhibitor. Prepn: S. Karbach et al., EP 196038; eidem, US 4906652 (1986, 1990 both to BASF). Properties and field trials: E. Ammermann et al., Brighton Crop Prot. Conf. - Pests Dis. 1990, 407; R. Saur et al., ibid. 831. Mode of action: A. Akers et al., ibid. 837. Use in combination with fenpropimorph, q.v.: R. Saur et al., Gesunde Pflanz. 46, 61 (1994). Brief review: A. Floquet, N. Martin, Phytoma 449, 54-57 (1993).

Chemical structure

Properties

Crystals from diisopropyl ether, mp 136.2°. Soly at 20° (g/100 ml): water 6.63 × 10-4, acetone 18, dichloromethane 14, n-heptane <0.1. Partition coefficient (n-octanol/ water at pH 7) 3.44. LD50 in rats (mg/kg): >5000 orally, >2000 dermally; LC50 in rats (4 hr): >5.3 mg/l (dust aerosol) (Ammermann).

Use

Agricultural fungicide.