NOMENCLATURE

Common name flutriafol (BSI, ANSI, draft E-ISO, (m) draft F-ISO)

IUPAC name (RS)-2,4'-difluoro-a-(1H-1,2,4-triazol-1-ylmethyl)benzhydryl alcohol 

Chemical Abstracts name (?-a-(2-fluorophenyl)-a-(4-fluorophenyl)-1H-1,2,4-triazole-1-ethanol 

CAS RN [76674-21-0]  Development codes PP450 (ICI) 

PHYSICAL CHEMISTRY

Mol. wt. 301.3  M.f. C₁₆H₁₃F₂N₃O  Form White, crystalline solid.  M.p. 130 ºC  V.p. 7.1 ´ 10^-6 mPa (20 ºC)  K_OW logP = 2.3 (20 ºC)  Henry 1.65 ´ 10^-8 Pa m³ mol^-1 (calc.)  S.g./density 1.41 g/ml (25 ºC)  Solubility In water 130 mg/l (pH 7, 20 ºC). In acetone 190, dichloromethane 150, methanol 69, xylene 12, hexane 0.3 (all in g/l, 20 ºC). 

APPLICATIONS

Biochemistry Inhibits ergosterol biosynthesis (steroid demethylation inhibitor), causing fungal cell wall collapse and inhibition of hyphal growth.  Mode of action Contact and systemic fungicide with eradicant and protective action. Absorbed by the foliage, with translocation acropetally in the xylem.  Uses Control of a broad spectrum of leaf and ear diseases (including Erysiphe graminis, Rhynchosporium secalis, and Septoria, Puccinia, and Helminthosporium spp.) in cereals, at 125 g a.i./ha. Also used in non-mercurial seed treatment formulations to control the major soil-borne and seed-borne diseases of cereals.  Formulation types SC. 

ANALYSIS

Residues by glc; details from Syngenta.

MAMMALIAN TOXICOLOGY

Oral Acute oral LD₅₀ for male rats 1140, female rats 1480 mg/kg.  Skin and eye Acute percutaneous LD₅₀ for rats >1000, rabbits >2000 mg/kg. Mild eye irritant; non-irritating to skin (rabbits). Not a skin sensitiser.  Inhalation LC₅₀ (4 h) for rats >3.5 mg/l.  NOEL In 90 d feeding trials, rats receiving 2 mg/kg diet, and dogs receiving 5 mg/kg daily showed no ill-effects. Non-teratogenic in rats and rabbits.  Other Non-cytogenic in in vivo studies. Non-mutagenic in the Ames assay.  Toxicity class WHO (a.i.) III; EPA (formulation) III  EC hazard (Xn; R20/21/22| R52, R53) 

ECOTOXICOLOGY

Birds Acute oral LD₅₀ for female mallard ducks >5000 mg/kg. Dietary LC₅₀ (5 d)  for mallard ducks 3940, Japanese quail 6350 mg/kg.  Fish LC₅₀ (96 h) for rainbow trout 61, mirror carp 77 mg/l. NOEC 6.2 mg/l.  Daphnia LC₅₀ (48 h) 78 mg/l.  Bees Low toxicity to honeybees. Acute oral LD₅₀ >5 mg/bee.  Worms LC₅₀ (14 d) >1000 mg/kg. 

ENVIRONMENTAL FATE

Soil/Environment Flutriafol has no effect on microbial populations, or on the carbon or nitrogen transformations occurring in the soil.