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Flusilazole

Fungicide

FRAC 3; DMI: triazole

NOMENCLATURE

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

IUPAC namebis(4-fluorophenyl)(methyl)(1H-1,2,4-triazol-1-ylmethyl)silane; 1-[[bis(4-fluorophenyl)(methyl)silyl]methyl]-1H-1,2,4-triazole

Chemical Abstracts name1-[[bis(4-fluorophenyl)methylsilyl]methyl]-1H-1,2,4-triazole

CAS RN[85509-19-9]Development codesDPX-H 6573 (Du Pont)

Flusilazole PHYSICAL CHEMISTRY
CompositionTech. is 92.5%.Mol. wt.315.4M.f.C16H15F2N3SiFormWhite, odourless crystals.M.p.53-55 ºCV.p.3.9 ´ 10-2mPa (25 ºC, gas saturation method)KOWlogP = 3.74 (pH 7, 25 ºC)Henry2.7 ´ 10-4Pa m3mol-1(pH 8, 25 °C, calc.)S.g./density1.30SolubilityIn water 45 (pH 7.8), 54 (pH 7.2), 900 (pH 1.1) (all in mg/l, 20 ºC). Readily soluble (>2 kg/l) in many organic solvents.StabilityStable for more than 2 years under normal storage conditions. Stable to light, and to temperatures up to 310 ºC.pKa2.5, v. weak base

Flusilazole COMMERCIALISATION
HistoryFungicide reported by T. M. Fort & W. K. Moberg (Proc. Br. Crop Prot. Conf. - Pests Dis., 1984, 1, 413). Introduced in France (1985) by E. I. du Pont de Nemours and Co.ManufacturersDu Pont

Fusilazole APPLICATIONS
BiochemistryInhibits ergosterol biosynthesis (steroid demethylation inhibitor).Mode of actionSystemic fungicide with protective and curative action. Its resistance to wash-off, redistribution by rainfall and vapour phase activity are important components in its biological activity.UsesBroad spectrum, systemic, preventive and curative fungicide effective against many pathogens (Ascomycetes, Basidiomycetes and Deuteromycetes). It is recommended for use on many crops, such as: apples (Venturia inaequalis,Podosphaera leucotricha); peaches (Sphaerotheca pannosa, Monilia laxa); cereals (all major diseases); grapes (Uncinula necator, Guignardia bidwellii); sugar beet (Cercospora beticola, Erysiphe betae); maize (Helminthosporium turcicum); sunflowers (Phomopsis helianthi); oilseed rape (Pseudocercosporella capsellae, Pyrenopeziza brassicae); bananas (Mycosphaerella spp.).Formulation typesEC; EW; SC; SE; WG.Selected tradenames:'Capitan' (cereals) (Du Pont); 'Nustar' (fruit) (Du Pont); 'Olymp' (fruit) (Du Pont); 'Punch' (cereals) (Du Pont); 'Sanction' (cereals) (Du Pont)

Flusilazole ANALYSIS
Product by gc. Details from Du Pont. Residues determined by gc (R. A. Guinivan & M. R. Gagnon, J. Assoc. Off. Anal. Chem. Int., 77, 728 (1994)).

Flusilazole MAMMALIAN TOXICOLOGY
ReviewsFAO/WHO 74, 76 (see part 2 of the Bibliography).OralAcute oral LD50for male rats 1100, female rats 674 mg/kg.Skin and eyeAcute percutaneous LD50for rabbits >2000 mg/kg; a mild irritant to skin and eyes, but not a skin sensitiser.InhalationLC50for male rats 27, female rats 3.7 mg/l air.NOEL(2 y) for rats 10 mg/kg diet; (1 y) for dogs 5 mg/kg diet; (1.5 y) for mice 25 mg/kg diet.ADI(JMPR) 0.001 mg/kg b.w. [1995].OtherNot mutagenic.Toxicity classWHO (a.i.) III

Flusilazole ECOTOXICOLOGY
BirdsAcute oral LD50for mallard ducks >1590 mg/kg.FishLC50(96 h) for rainbow trout 1.2, bluegill sunfish 1.7 mg/l.DaphniaLC50(48 h) 3.4 mg/l.BeesNot toxic to bees. LD50>150 mg/bee.

flusilazole ENVIRONMENTAL FATE

Soil/EnvironmentResults of several different studies under varying environmental conditions indicate average DT5095 d.