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Cyproconazole

Cyproconazole 95%TC
Cyproconazole 40%SC
Cyproconazole 25%EC
Cyproconazole 10%WDG

Fungicide
FRAC 3, G1; DMI: triazole

Cyproconazole NOMENCLATURE
Common name cyproconazole (BSI, draft E-ISO, (m) draft F-ISO)
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 -(4-chlorophenyl)--(1-cyclopropylethyl)-1H-1,2,4-triazol-1-ethanol
CAS RN [94361-06-5] unstated stereochemistry; [94361-07-6] (2RS,3SR) isomers; [113096-99-4] former number Development codes SAN 619 F (Sandoz)

Cyproconazole PHYSICAL CHEMISTRY
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 ºC V.p. 2.6  10-2 mPa (25 ºC) KOW logP = 3.1 Henry 2.6  10-4 Pa m3 mol-1 S.g./density 1.25 g/cm3 Solubility In water 93 mg/l (22 ºC). In acetone 360, ethanol 230, methanol 410, dimethyl sulfoxide 180, xylene 120, toluene 100, dichloromethane 430, ethyl acetate 240, hexane 1.3, octanol 100, (all in g/l, 25 ºC). Stability Decomposition is <5% after storage for 2 years. Stable in aqueous solutions at pH 1-9 for a test period of 35 days (50 ºC) or 14 days (80 ºC). Slowly hydrolysed in 1N HCl and NaOH. pKa No acid or base properties in range pH 3.5-10. F.p. No reaction up to 360 ºC

COMMERCIALISATION
History Fungicide reported by U. Gisi et 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

Cyproconazole APPLICATIONS
Biochemistry Steroid 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 SC; SL; WG. Selected products: 'Alto' (Syngenta); 'Caddy' (Bayer CropScience); mixtures: 'Radius' (+ cyprodinil) (Syngenta)