Fungicide

FRAC  3; DMI: triazole

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 a-(4-chlorophenyl)-a-(1-cyclopropylethyl)-1H-1,2,4-triazol-1-ethanol 

CAS RN [94361-06-5] for (2RS,3RS;2RS,3SR) isomers; [113096-99-4] for unstated stereochemistry; [94361-07-6] for (2RS,3SR) isomers  Development codes SAN 619 F (Sandoz) 

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. 106-109 ºC  B.p. >250 ºC  V.p. 3.46 ´ 10-2 mPa (20 ºC)  KOW logP = 2.91 (pH 7)  S.g./density 1.259 g/cm3  Solubility In water 140 mg/l (25 ºC). In acetone 230, ethanol 230, dimethyl sulfoxide 180, xylene 120 (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

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 tradenames: 'Alto' (Bayer, Syngenta); 'Shandon' (Barclay); mixtures: 'Radius' (+ cyprodinil) (Syngenta)

OTHER TRADENAMES

'Atemi' (Syngenta); 'Bialor' (Syngenta); 'Epicure' (Syngenta); 'Paindor' (Syngenta); 'Solima' (Syngenta); 'Synchro' (Syngenta); 'Tiptor' (Syngenta); 'Vitocap' (Syngenta); 'Barclay Shandon' (Barclay); 'Gentian' (GreenCrop) mixtures: 'Artea' (+ propiconazole) (Syngenta); 'Iridia' (+ cyprodinil) (France) (Syngenta); 'Menara' (+ propiconazole) (Syngenta); 'Octolan' (+ chlorothalonil) (Syngenta); 'Agora' (+ trifloxystrobin) (Bayer); 'Alto Ambel' (+ carbendazim) (Syngenta, Bayer); 'Alto Combi' (+ carbendazim) (Syngenta, Bayer); 'Alto Elite' (+ chlorothalonil) (Syngenta, Bayer); 'Profile' (+ prochloraz) (Aventis); 'Sportak Delta' (+ prochloraz) (Aventis); 'Spot Light' (+ thiophanate-methyl) (Aventis); 'Tiptor' (+ prochloraz) (Aventis) Discontinued names: 'Aplan' * (Novartis) mixtures: 'Alto Major' * (+ tridemorph) (Novartis); 'Moot' * (+ tridemorph) (Novartis)

ANALYSIS

Product analysis by glc or hplc. Residues determined by glc. 

MAMMALIAN TOXICOLOGY

Oral Acute oral LD50 for male rats 1020, 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 1 mg/kg b.w. daily; (2 y) for rats 1 mg/kg b.w. daily.  Other Not mutagenic in the Ames assay.  Toxicity class WHO (a.i.) II  EC hazard (R22) 

ECOTOXICOLOGY

Birds Acute oral LD50 for Japanese quail 150 mg/kg. Dietary LC50 (8 d) for Japanese quail 816, mallard ducks 1197 mg/kg diet.  Fish LC50 (96 h) for carp 18.9, trout 19, bluegill sunfish 21 mg/l.  Daphnia LC50 (48 h) 26 mg/l.  Bees LD50 (contact) >0.1 mg/bee; (oral) >1 mg/bee. 

ENVIRONMENTAL FATE