Epoxiconazole

NOMENCLATURE
Common name époxiconazole ((m) F-ISO); epoxiconazole (BSI, E-ISO) IUPAC name (2RS,3SR)-1-[3-(2-chlorophenyl)-2,3-epoxy-2-(4-fluorophenyl)propyl]-1H-1,2,4-triazole
Chemical Abstracts name cis-1-[[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiranyl]methyl]-1H-1,2,4-triazole CAS RN [133855–98–8], formerly [106325–08–0] and [205862–63–1]; [135319–73–2] stereochemistry undefined EC no. 406–850–2
PHYSICAL CHEMISTRY
Composition Material is the 2R,3S- 2S,3R- enantiomer pair. Mol. wt. 329.8 M.f. C₁₇H₁₃ClFN₃O Form Colourless crystals. M.p. 136.2–137 °C V.p. <0.01 mPa (20 °C) K_ow logP = 3.33 (pH 7) Henry <4.71 × 10^-4 Pa m³ mol^-1 (calc.) S.g./density 1.384 (room temperature) Solubility In water 6.63 × 10^-4 g/100 ml (20 °C). In acetone 14.4, dichloromethane 29.1, heptane 0.04 (all in g/100 ml). Stability No hydrolysis at pH 5 and pH 7 within 12 days.
APPLICATIONS
Biochemistry Inhibition of C-14-demethylase in sterol biosynthesis. Mode of action Preventive and curative fungicide. Uses Broad-spectrum Fungicide, with preventive and curative action, for control of diseases caused by Ascomycetes, Basidiomycetes and Deuteromycetes in bananas, cereals, coffee, rice, corn, peanut and sugar beet, generally at 125 g/ha. Formulation types EC; SC; SE. Compatibility Compatible with morpholines, MBC-derivatives, azoles, strobilurins and carboxamides.
ENVIRONMENTAL FATE
Animals A.i. is readily excreted via faeces. There are no major metabolites, but a high number of minor metabolites was identified. The important metabolic reactions were cleavage of the oxirane ring, hydroxylation of the phenyl rings and conjugation. Plants There is extensive degradation. Soil/Environment Degradation in soil is by microbial activity, DT₅₀ c. 2–3 mo. K_oc 957–2647.
MAMMALIAN TOXICOLOGY
Oral Acute oral LD₅₀ for rats >5000 mg/kg. Skin and eye Acute percutaneous LD₅₀ for rats >2000 mg/kg. Non-irritating to eyes and skin of rabbits. Inhalation LC₅₀ (4 h) for rats >5.3 mg/l air. NOEL (carcinogenicity) for mice 0.81 mg/kg b.w. ADI (EC) 0.008 mg/kg b.w. [2008]; (EPA) aRfD 0.05, cRfD 0.02 mg/kg [2006]. EC classification R40| R62| R63| N; R51, R53 
ECOTOXICOLOGY
Birds Acute oral LD₅₀ for quail >2000 mg/kg. LC₅₀ for quail 5000 mg/kg. Fish LC₅₀ (96 h) for trout 2.2–4.6, bluegill sunfish 4.6–6.8 mg/kg. Daphnia LC₅₀ (48 h) 8.7 mg/l. Algae EC₅₀ (72 h) for green algae 2.3 mg/l. Bees LD₅₀ >100 μg/bee. Worms EC₅₀ (14 d) >1000 mg/kg soil.