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224 cyproconazole Fungicide
FRAC 3, G1 SBI Class I, DMI: triazole

Common name cyproconazole (BSI, E-ISO, (m) F-ISO, not Canada) IUPAC name (2RS,3RS;2RS,3SR)-2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
Chemical Abstracts name α-(4-chlorophenyl)-α-(1-cyclopropylethyl)-1H-1,2,4-triazol-1-ethanol CAS RN [94361–06–5] unstated stereochemistry, formerly [113096–99–4]; [94361–07–6] (2RS,3SR)- isomers Development codes SAN 619 F (Sandoz) Smiles code CC(C1CC1)C(O)(Cn2cncn2)c3ccc(Cl)cc3
Composition It is a mixture (c. 1:1) of 2 diastereoisomers. Mol. wt. 291.8 M.f. C15H18ClN3O Form Colourless solid. M.p. 106.2–106.9°C B.p. >250°C V.p. 2.6 × 10-2 mPa (25°C) Kow logP = 3.1 Henry 5.0 × 10-5Pa m3 mol-1S.g./density 1.25 g/cm3Solubility In water 93 mg/l (22°C). In acetone 360, ethanol 230, methanol 410, DMSO 180, xylene 120, toluene 100, dichloromethane 430, ethyl acetate 240, hexane 1.3, octanol 100 (all in g/l, 25°C). Stability Oxidative decomposition starts at c. 115°C, followed by thermal decomposition starting at c. 300°C. Hydrolytically stable between pH 4 and 9, at 50°C, for 5 days. pKa No acid or base properties in range pH 3.5–10. F.p. No reaction up to 360°C
History Fungicide reported by U. Gisiet al. (Proc. Br. Crop Prot. Conf., 1986, 1, 33; 2, 857). Introduced in France and Switzerland (1989) by Sandoz AG (now Syngenta AG).Patents US 4664696 Manufacturers Syngenta; Fertiagro; Suzhou Hengtai
Biochemistry Sterol demethylation inhibitor.Mode of action Systemic fungicide with protective, curative, and eradicant action.Absorbed rapidly by the plant, with translocation acropetally.Uses Foliar, systemic fungicide for control of Septoria, rust, powdery mildew, Rhynchosporium, Cercospora and Ramularia in cereals and sugar beet, at 60–100 g/ha; and rust, Mycena, sclerotinia and Rhizoctonia in coffee and turf. Formulation types EC; SC; SL; WG.
Selected products 'Akenaton' (Rocca) ; 'Alto' (Syngenta) ; 'Caddy' (Bayer CropScience) mixtures 'Menara' (+ propiconazole) (Syngenta, Syngenta) ; 'Sphere' (+ trifloxystrobin) (Bayer CropScience, Bayer CropScience) ; 'Aproach Prima' (+ picoxystrobin) (DuPont, DuPont) Other products 'Atemi' (Syngenta) ; 'Bialor' (Syngenta) ; 'Caddy Arbo' (Bayer CropScience) ; 'Cipren' (Chemia) ; 'Fort' (Bayer CropScience) ; 'Mohawk' (Bayer CropScience) ; 'Paindor' (Syngenta) ; 'Shandon' (Barclay) ; 'Solima' (Syngenta) ; 'Synchro' (Syngenta) ; 'Vitocap' (Syngenta) mixtures 'Agora' (+ trifloxystrobin) (Bayer CropScience, Bayer CropScience) ; 'Aldus' (+ quinoxyfen) (Dow AgroSciences, Dow AgroSciences) ; 'Alto Ambel' (+ carbendazim) (Syngenta, Syngenta) ; 'Alto Combi' (+ carbendazim) (Syngenta, Syngenta) ; 'Alto Elite' (+ chlorothalonil) (Syngenta, Syngenta) ; 'AmistarXtra' (+ azoxystrobin) (Syngenta, Syngenta) ; 'Artea' (+ propiconazole) (Syngenta, Syngenta) ; 'Cherokee' (Europe, Africa, Middle East) (+ chlorothalonil + propiconazole) (Syngenta, Syngenta, Syngenta) ; 'Divora' (+ quinoxyfen + quinoxyfen) (Dow AgroSciences, Dow AgroSciences, Syngenta, Syngenta) ; 'Epicure' (+ prochloraz) (Syngenta, Syngenta) ; 'Escolta' (+ trifloxystrobin) (Bayer CropScience, Bayer CropScience) ; 'Excelsior' (+ quinoxyfen) (Interfarm, Interfarm) ; 'Iridia' (France) (+ cyprodinil) (Syngenta, Syngenta) ; 'Maxim Star' (seed treatment) (+ fludioxonil) (Syngenta, Syngenta) ; 'Priori Xtra' (+ azoxystrobin) (Syngenta, Syngenta) ; 'Profile' (+ prochloraz) (BASF, BASF) ; 'Radius' (+ cyprodinil) (Syngenta, Syngenta) ; 'Sfera' (+ trifloxystrobin) (Bayer CropScience, Bayer CropScience) ; 'Sportak Delta' (+ prochloraz + prochloraz) (BASF, BASF, Makhteshim, Makhteshim) ; 'Stinger' (cereals, soya beans) (+ picoxystrobin) (DuPont, DuPont) ; 'Tiptor S' (+ prochloraz) (Syngenta, Syngenta) ; 'Zardex' (seed treatment) (+ guazatine acetates) (Syngenta, Syngenta) ; 'Verdadero 600' (+ thiamethoxam) (Syngenta, Syngenta) ; 'Solitär' (seed treatment, Switzerland) (+ cyprodinil + fludioxonil) (Syngenta, Syngenta, Syngenta) Discontinued products 'Aplan *' (Novartis) mixtures 'Alto Major *' (+ tridemorph + tridemorph) (Novartis, Novartis, Sandoz, Sandoz) ; 'Moot *' (+ tridemorph) (Novartis, Novartis) ; 'Octolan *' (+ chlorothalonil) (Novartis, Novartis) ; 'Spot Light *' (+ thiophanate-methyl) (Bayer CropScience, Bayer CropScience)
Product analysis by rp hplc with uv detection (CIPAC Handbook, 2000, J, 29). Product analysis by glc or hplc.Residues determined by glc.
Animals In mammals, following oral administration, cyproconazole is rapidly absorbed, extensively metabolised and excreted, DT50c. 30 h. No bioaccumulation. Plants In different crops, metabolic pathways are similar and the major residue is cyproconazole itself. Soil/Environment In soil, cyproconazole degrades moderately quickly, DT50c. 4 mo. (lab., n=8), c. 40 d (field, n=37). No accumulation and leaching potential. Soil adsorption FreundlichKoc 364 ml/g. Hydrolytically and photolytically stable. In aquatic systems (n=2) DT50 5.6 d (water), >1 y (whole system).
JMPREvaln. I 120 (2010); EU Rev. Rep.SANCO/10344/2011 (2011); EFSAJou.2010, 8(11), 1897 [73 pp.].EU Status (1107/2009) Approved, 2011/56/EU.
Oral Acute oral LD50 for male rats 350, female rats 1333, male mice 200, female mice 218 mg/kg.Skin and eye Acute percutaneous LD50 for rats and rabbits >2000 mg/kg. Non-irritating to skin and eyes (rabbits).Non-irritating to skin, and not a skin sensitiser (guinea pigs).Inhalation LC50 (4 h) for rats >5.65 mg/l air.NOEL (1 y) for dogs 3.2 mg/kg b.w. daily; (2 y) for rats 2 mg/kg b.w. daily.ADI (BfR) 0.01 mg/kg b.w. [2002]; (company proposed value, ECDAR) 0.02 mg/kg b.w. [2006]; (EPA) 0.01 mg/kg b.w. [1993].Other Not mutagenic in the Ames assay. Toxicity class WHO (a.i.) III. EC classification (R63| Xn; R22| N; R50, R53)
Birds Acute oral LD50 for bobwhite quail 131 mg/kg (geomean of 2 tests). Dietary LC50 (5 d) for bobwhite quail 856 (geomean of 2 tests), mallard ducks 851 mg/kg diet. Fish LC50 (96 h) for carp 20, trout 19, bluegill sunfish 21 mg/l. Daphnia LC50 (48 h) >26 mg/l. Algae EC50 (96 h) for Scenedesmussubspicatus 0.077 mg/l. Bees LD50 (contact, 24 h) >0.1 mg/bee; (oral, 24 h) >1 mg/bee.Worms LC50 (14 d) 335 mg/kg dry soil.

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