Epoxiconazole

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

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  KOW 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. 

COMMERCIALISATION

History Developed and introduced by BASF AG; first registrations in 1993.  Patents EP 94564; US 4464381  Manufacturers BASF

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 cereals, sugar beet, peanuts, oilseed rape, and ornamentals, generally at 125 g/ha.  Formulation types SC; SE.  Compatibility Compatible with morpholines and MBC-derivatives. 

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 0.0032 mg/kg daily. 

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

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. Koc 957-2647.