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Cyprodinil

Cyprodinil 98%TC
Cyprodinil 75%WG
Cyprodinil 50%WG

Fungicide
FRAC 9, D1; anilinopyrimidine

Cyprodinil NOMENCLATURE
Common name cyprodinil (pa ISO)
IUPAC name 4-cyclopropyl-6-methyl-N-phenylpyrimidin-2-amine
Chemical Abstracts name 4-cyclopropyl-6-methyl-N-phenyl-2-pyrimidinamine
CAS RN [121552-61-2] Development codes CGA 219417 (Ciba-Geigy)

Cyprodinil PHYSICAL CHEMISTRY
Mol. wt. 225.3 M.f. C14H15N3 Form Fine beige powder, with a weak odour. M.p. 75.9 ºC V.p. 5.1 10-1 mPa (crystal modification A); 4.7 10-1 mPa (crystal modification B) (both 25 ºC) KOW logP = 3.9 (pH 5.0), 4.0 (pH 7.0), 4.0 (pH 9.0) (25 ºC) Henry 6.6  10-3 to 7.2  10-3 Pa m3 mol-1 (calc., depending on crystal modification) S.g./density 1.21 (20 ºC) Solubility In water 20 (pH 5.0), 13 (pH 7.0), 15 (pH 9.0) (all in mg/l, 25 ºC). In ethanol 160, acetone 610, toluene 440, n-hexane 26, n-octanol 140 (all in g/l, 25 ºC). Stability Hydrolytically stable: DT50 in pH range 4-9 (25 ºC) >>1 y. Photolysis DT50 in water 5-30 d. pKa 4.44, weak base

COMMERCIALISATION
History Reported by U. J. Heye et al. (Proc. Br. Crop Prot. Conf. - Pests Dis.,1994, 2, 501). Developed and introduced by Ciba-Geigy AG (now Syngenta AG). First marketed in 1994. Patents EP 310550 Manufacturers Syngenta

Cyprodinil APPLICATIONS
Biochemistry Proposed inhibitor of the biosynthesis of methionine and the secretion of fungal hydrolytic enzymes. There is no cross resistance to benzimidazoles, carbamates, dicarboximides, imidazoles, morpholines, quinolines, strobilurins or triazoles. Mode of action Systemic product, with uptake into plants after foliar application and transport throughout the tissue and acropetally in the xylem. Inhibits penetration and mycelial growth both inside and on the leaf surface. Uses As a foliar fungicide for use in cereals, grapes, pome fruit, stone fruit, strawberries, vegetables, field crops and ornamentals; and as a seed dressing on barley. Controls a wide range of pathogens, such as Tapesia yallundae and T. acuformis, Erysiphe spp., Pyrenophora teres, Rhynchosporium secalis, Botrytis spp., Alternaria spp., Venturia spp. and Monilinia spp., at 150-750 g/ha. Formulation types EC; WG. Compatibility Some incompatibility problems have been reported when added to liquid formulations, but not if mixed in reverse order. Selected products: 'Chorus' (Syngenta); 'Unix' (Syngenta); 'Amtrak' (Barclay); mixtures: 'Radius' (+ cyproconazole) (Syngenta); 'Stereo' (+ propiconazole) (Syngenta); 'Switch' (+ fludioxonil) (foliar) (Syngenta)