Fungicide Epoxiconazole

NOMENCLATURE Epoxiconazole

Common name epoxiconazole (BSI, pa 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 [106325-08-0] EEC no. 406-850-2 Development codes BAS 480F (BASF) 

PHYSICAL CHEMISTRY Epoxiconazole

Composition Material is the 2R,3S- 2S,3R- enantiomer pair. Mol. wt. 329.8 M.f. C₁₇H₁₃ClFN₃O Form Colourless crystals. M.p. 136.2 ºC V.p. <0.01 mPa at 20 ºC K_OW logP = 3.44 (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 ºC). 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. 

MAMMALIAN TOXICOLOGY Epoxiconazole

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 0.0032 mg/kg daily. 

ECOTOXICOLOGY Epoxiconazole

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 mg/bee. Worms EC₅₀ (14 d) >1000 mg/kg soil. 

ENVIRONMENTAL FATE Epoxiconazole

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.