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FRAC 12, E2 phenylpyrrole

Common name fludioxonil (BSI, E-ISO, (m) F-ISO) IUPAC name 4-(2,2-difluoro-1,3-benzodioxol-4-yl)pyrrole-3-carbonitrile
Chemical Abstracts name 4-(2,2-difluoro-1,3-benzodioxol-4-yl)-1H-pyrrole-3-carbonitrile CAS RN [131341–86–1] Development codes CGA 173506 (Ciba-Geigy) Smiles code FC1(F)Oc2cccc(c3c[nH]cc3C#N)c2O1
Mol. wt. 248.2 M.f. C12H6F2N2O2 Form Yellowish crystals. M.p. 199.8 °C V.p. 3.9 × 10-4 mPa (25 °C) Kow logP = 4.12 (25 °C) Henry 5.4 × 10-5Pa m3 mol-1 (calc.) S.g./density 1.54 (20 °C) Solubility In water 1.8 mg/l (25 °C). In acetone 190, ethanol 44, toluene 2.7, n-octanol 20 and hexane 0.01 (all in g/l, 25 °C). Stability Practically no hydrolysis at 25 °C between pH 5 and 9. pKa pKa1<0; pKa2c. 14.1
History Announced by Ciba-Geigy AG (now Syngenta AG) as a novel fungicide for seed treatment (Proc. Br. Crop Prot. Conf. - Pests Dis., 1990, 2, 825–830) and foliar use (ibid., pp. 399–406). First sales in 1993 as a cereal seed dressing and in 1995 as a foliar fungicide, both in France. Patents EP 206999; US 4705800 Manufacturers Syngenta
Biochemistry Inhibits mitogen-activated protein kinase, in osmotic signal transduction. Mode of action Non-systemic fungicide with long residual activity. Uptake into the plant tissues and curative properties are generally limited. Inhibits mainly the germination of conidia and, to a lesser extent, the germ tube and mycelial growth. Uses As a seed treatment, for control of Fusarium, Microdochium, Rhizoctonia, Tilletia, Pyrenophora and Septoria spp., in both cereal and non-cereal crops, at 2.5–10 g/100 kg. As a foliar fungicide, for control of Botrytis, Monilinia, sclerotinia, and Alternaria spp., in grapes, stone fruit, berry crops, vegetables and ornamentals, at 250–500 g/ha; also on turf, against Fusarium, Helminthosporium, Rhizoctonia, sclerotinia and Typhula, at 400–800 g/ha. Also as a post-harvest treatment on stone fruit, pome fruit, citrus and kiwi, at 30–60 g/hl, against Botrytis, Monilinia and Penicillium spp. Formulation types DS; FS; SC; WG; WP.
Selected products ‘Celest’ (seed treatment) (Syngenta) ; ‘Géoxe’ (foliar) (Syngenta) mixtures ‘Switch’ (foliar) (+ cyprodinil) (Syngenta, Syngenta) Other products ‘Atlas’ (seed treatment) (Syngenta) ; ‘Cannonball’ (Syngenta) ; ‘Graduate’ (post-harvest) (Syngenta) ; ‘Maxim’ (seed treatment) (Syngenta) ; ‘Medallion’ (Syngenta) ; ‘Saphire’ (foliar) (Syngenta) ; ‘Savior’ (foliar) (Syngenta) ; ‘Scholar’ (post-harvest) (Syngenta) mixtures ‘Apron Maxx’ (+ metalaxyl-M) (Syngenta, Syngenta) ; ‘Arena C’ (seed treatment, Germany) (+ tebuconazole) (Bayer CropScience, Bayer CropScience) ; ‘Austral Plus’ (seed treatment) (+ anthraquinone + tefluthrin) (Syngenta, Syngenta, Syngenta) ; ‘Botryl’ (ornamentals) (+ cyprodinil) (Syngenta, Syngenta) ; ‘Celest Extra’ (+ difenoconazole) (Syngenta, Syngenta) ; ‘CruiserMaxx Beans’ (seed treatment) (+ metalaxyl-M + thiamethoxam) (Syngenta, Syngenta, Syngenta) ; ‘CruiserMaxx Potato’ (seed treatment) (+ thiamethoxam) (Syngenta, Syngenta) ; ‘Cruiser OSR’ (seed treatment) (+ metalaxyl-M + thiamethoxam) (Syngenta, Syngenta, Syngenta) ; ‘Dynasty’ (seed treatment) (+ azoxystrobin + metalaxyl-M) (Syngenta, Syngenta, Syngenta) ; ‘Helix’ (seed treatment) (+ difenoconazole + metalaxyl-M + thiamethoxam) (Syngenta, Syngenta, Syngenta, Syngenta) ; ‘Justmeet’ (Japan) (+ fenhexamid) (Bayer CropScience, Bayer CropScience) ; ‘Justmeet’ (+ fenhexamid) (Bayer CropScience, Bayer CropScience) ; ‘Landor CT’ (seed treatment, Germany) (+ tebuconazole + difenoconazole) (Syngenta, Syngenta, Syngenta) ; ‘Maxim MZ’ (seed treatment) (+ mancozeb) (Syngenta, Syngenta) ; ‘Maxim Star’ (seed treatment) (+ cyproconazole) (Syngenta, Syngenta) ; ‘Maxim XL’ (seed treatment) (+ metalaxyl-M) (Syngenta, Syngenta) ; ‘Momiguard C’ (seed treatment) (+ pefurazoate + copper oxychloride + pefurazoate + copper oxychloride + pefurazoate + copper oxychloride) (Hokko, Hokko, Hokko, SDS Biotech K.K., SDS Biotech K.K., SDS Biotech K.K., Syngenta, Syngenta, Syngenta) ; ‘Seed Shield’ (+ azoxystrobin + metalaxyl-M + difenoconazole) (Helena, Helena, Helena, Helena) ; ‘Wakil XL’ (seed treatment) (+ cymoxanil + metalaxyl-M) (Syngenta, Syngenta, Syngenta) ; ‘CruiserMaxx Rice’ (seed treatment) (+ azoxystrobin + metalaxyl-M + thiamethoxam) (Syngenta, Syngenta, Syngenta, Syngenta) ; ‘Avicta Complete Beans’ (seed treatment) (+ abamectin + thiamethoxam + metalaxyl-M) (Syngenta, Syngenta, Syngenta, Syngenta) ; ‘Maxim Quattro’ (seed treatment) (+ thiabendazole + azoxystrobin + metalaxyl-M) (Syngenta, Syngenta, Syngenta, Syngenta) ; ‘CruiserMaxx Plus’ (seed treatment) (+ metalaxyl-M + thiamethoxam) (Syngenta, Syngenta, Syngenta) ; ‘CruiserMaxx Sugarbeets’ (+ thiamethoxam + metalaxyl-M) (Syngenta, Syngenta, Syngenta) ; ‘Vibrance Integral’ (seed treatment) (+ difenoconazole + thiamethoxam + sedaxane) (Syngenta, Syngenta, Syngenta, Syngenta) ; ‘FarMore F1500’ (+ thiamethoxam + azoxystrobin + spinosad+ metalaxyl-M) (Syngenta, Syngenta, Syngenta, Syngenta, Syngenta) ; ‘Astaund’ (+ cyprodinil) (Syngenta, Syngenta) ; ‘Palladium’ (+ cyprodinil) (Syngenta, Syngenta) ; ‘Celest Orge Net’ (seed treatment, France) (+ tebuconazole + cyprodinil) (Syngenta, Syngenta, Syngenta) ; ‘Solitär’ (seed treatment, Switzerland) (+ cyprodinil + cyproconazole) (Syngenta, Syngenta, Syngenta) ; ‘Celest Trio’ (seed treatment) (+ difenoconazole + tebuconazole) (Syngenta, Syngenta, Syngenta) ; ‘Celest Top’ (seed treatment) (+ difenoconazole + thiamethoxam) (Syngenta, Syngenta, Syngenta) ; ‘Cruiser Advanced’ (seed treatment) (+ thiabendazole + metalaxyl-M) (Syngenta, Syngenta, Syngenta) ; ‘Cruiser Extreme’ (seed treatment) (+ metalaxyl-M + thiamethoxam + azoxystrobin) (Syngenta, Syngenta, Syngenta, Syngenta) ; ‘Cruiser Maxx Cereals’ (seed treatment) (+ metalaxyl-M + thiamethoxam + difenoconazole) (Syngenta, Syngenta, Syngenta, Syngenta) ; ‘Hurricane’ (ornamentals) (+ metalaxyl-M) (Syngenta, Syngenta) ; ‘Vibrance Gold’ (seed treatment) (+ sedaxane + difenoconazole) (Syngenta, Syngenta, Syngenta) ; ‘Cruiser Maxx’ (PM16 Q) (+ thiamethoxam + metalaxyl-M) (Syngenta, Syngenta, Syngenta) ; ‘Apron Maxx Advanced’ (+ thiabendazole + metalaxyl-M) (Syngenta, Syngenta, Syngenta) ; ‘Maxim Forte’ (+ tebuconazole + azoxystrobin) (Syngenta, Syngenta, Syngenta) ; ‘Vibrance XL’ (+ sedaxane + metalaxyl-M + difenoconazole + thiamethoxam) (Syngenta, Syngenta, Syngenta, Syngenta, Syngenta) ; ‘Helix Vibrance’ (+ difenoconazole + thiamethoxam + sedaxane) (Syngenta, Syngenta, Syngenta, Syngenta) ; ‘Cruiser Macc Vibrance Beans’ (+ sedaxane + metalaxyl-M + thiamethoxam) (Syngenta, Syngenta, Syngenta, Syngenta) Discontinued products ‘Elyxor *’ (Novartis) ; ‘Wispect *’ (Novartis) mixtures ‘Celest Orge’ (seed treatment, France) (+ anthraquinone + tebuconazole + cyprodinil) (Syngenta, Syngenta, Syngenta, Syngenta) ; ‘Cruiser Blé’ (seed treatment) (+ difenoconazole + thiamethoxam) (Syngenta, Syngenta, Syngenta) ; ‘Cruiser Blé Plus’ (seed treatment) (+ thiamethoxam + difenoconazole + tefluthrin) (Syngenta, Syngenta, Syngenta, Syngenta) ; ‘CruiserMaxx Sunflower *’ (+ metalaxyl-M + thiamethoxam + azoxystrobin) (Syngenta, Syngenta, Syngenta, Syngenta) ; ‘Elyxor Star *’ (+ tefluthrin + anthraquinone) (Syngenta, Syngenta, Syngenta) ; ‘Maxim Apron *’ (+ metalaxyl) (Syngenta, Syngenta) ; ‘Solitär’ (seed treatment, Germany) (+ cyprodinil + tebuconazole) (Syngenta, Syngenta, Syngenta)
Product by hplc/uv. Residues in crops or soil by hplc/uv and gc/MSD (Pestic. Anal. Man., II, 180.516; Resid. Anal. Methods; Environ. Chem. Methods).
Animals Well absorbed from the gastrointestinal tract, rapidly distributed in the body and completely excreted. The major metabolic reaction is the oxidation of the pyrrole ring at the 2- position. All metabolites are excreted as conjugates, mainly glucuronides. Plants Metabolism proceeds via oxidation at the pyrrole ring, followed by ring opening and the formation of pyrrolidine carboxylic acid. In general, fludioxonil is metabolised to more than 10–15 minor metabolites. Soil/Environment Formation of bound residues is the major route for dissipation in soil. Field DT50c. 14 d and c. 26–54 d after foliar and seed treatment use, respy. In leaching and adsorption/desorption experiments, the compound proved to be immobile in soil. Photolytic DT50 in water is 9–10 d (natural sunlight).
JMPR Mtg. 101 (2004), 107 (2006); JMPR Evaln. I 102 (2004), 108 (2006), 120 (2010); JMPR Evaln. II 104 (2004). EFSA Sci. Rep. (2007) 110, 1–85; EU Rev. Rep.SANCO/2818/07 (2007). EU Status (1107/2009) Approved, 2007/76/EC.
Oral Acute oral LD50 for rats and mice >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Non-irritating to eyes and skin (rabbits). Non-sensitising to skin (guinea pigs). Inhalation LC50 (4 h) for rats >2600 mg/m3 air. NOEL (2 y) for rats 40 mg/kg b.w. daily; (1.5 y) for mice 112 mg/kg b.w. daily; (1 y) for dogs 3.3 mg/kg b.w.. daily. ADI (JMPR) 0.4 mg/kg b.w. [2004, 2006]; (EC) 0.37 mg/kg b.w. [2007]; (EPA) 0.03 mg/kg b.w. [1995]. Other Not teratogenic, not mutagenic, not oncogenic. Toxicity class WHO (a.i.) U
Birds Acute oral LD50 for mallard ducks and bobwhite quail >2000 mg/kg. LC50 for mallard ducks and bobwhite quail >5200 ppm. Fish LC50 (96 h) for bluegill sunfish 0.74, catfish 0.63, common carp 1.5, rainbow trout 0.23 mg/l. Daphnia LC50 (48 h) 0.40 mg/l. Algae EC50 (72 h) for Scenedesmus subspicatus 0.93 mg/l; EbC50 for Selenastrum capricornutum 0.025 mg/l. Other aquatic spp. Non-toxic to sediment dweller, Chironomus riparius.Bees Non-toxic; LD50 (48 h, oral and contact) >100 μg/bee. Worms LC50 (14 d) for Eisenia foetida>1000 mg/kg soil. Other beneficial spp. Very low risk for beneficial arthropods.

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