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Propiconazole

Propiconazole 95%TC
Propiconazole 39%EC
Propiconazole 25%EC

Fungicide
FRAC 3, G1; DMI: triazole

Propiconazole NOMENCLATURE
Common name propiconazole (BSI, draft E-ISO, (m) draft F-ISO)
IUPAC name (?-1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole
Chemical Abstracts name 1-[[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole
CAS RN [60207-90-1] unstated stereochemistry EEC no. 262-104-4 Development codes CGA 64 250 (Ciba-Geigy)

Propiconazole PHYSICAL CHEMISTRY
Mol. wt. 342.2 M.f. C15H17Cl2N3O2 Form Yellowish, odourless, viscous liquid (tech.). M.p. -23 °C (glass transition temperature) B.p. 99.9 °C (0.32 Pa); 120 °C (1.9 Pa); >250 °C (101 kPa) V.p. 2.7 10-2 mPa (20 °C); 5.6 10-2 mPa (25 ºC) KOW logP = 3.72 (pH 6.6, 25 ºC) Henry 9.2  10-5 Pa m3 mol-1 (20 °C, calc.) S.g./density 1.29 (20 ºC) Solubility In water 100 mg/l (20 ºC). In n-hexane 47 g/l. Completely miscible with ethanol, acetone, toluene and n-octanol (25 °C). Stability Stable up to 320 ºC; no significant hydrolysis. pKa 1.09, v. weak base

COMMERCIALISATION
History Fungicide described by Janssen Pharmaceutica. Developed for agricultural uses by Ciba-Geigy AG (now Syngenta AG) and reported by P. A. Urech et al. (Proc. Br. Crop Prot. Conf., 1979, 2, 508) and first sold in 1980. Patents GB 1522657; BE 835579 to Janssen Manufacturers Dow AgroSciences; Fengle; Milenia; Nagarjuna Agrichem; Sannong; Sharda; Sundat; Syngenta

Propiconazole APPLICATIONS
Biochemistry Steroid demethylation (ergosterol biosynthesis) inhibitor. Mode of action Systemic foliar fungicide with protective and curative action, with translocation acropetally in the xylem. Uses Systemic foliar fungicide with a broad range of activity, at 100-150 g/ha. On cereals, it controls diseases caused by Cochliobolus sativus, Erysiphe graminis, Leptosphaeria nodorum, Puccinia spp., Pyrenophora teres, Pyrenophora tritici-repentis, Rhynchosporium secalis, and Septoria spp. In bananas, control of Mycosphaerella musicola and Mycosphaerella fijiensis var. difformis. Other uses are in turf against Sclerotinia homoeocarpa, Rhizoctonia solani, Puccinia spp. and Erysiphe graminis; in rice against Rhizoctonia solani, Helminthosporium oryzae, and dirty panicle complex; in coffee against Hemileia vastatrix; in peanuts against Cercospora spp.; in stone fruit against Monilinia spp., Podosphaera spp., Sphaerotheca spp. and Tranzschelia spp.; in maize against Helminthosporium spp. Formulation types EC; SC; GL. Selected products: 'Tilt' (Syngenta, Makhteshim-Agan); 'Bolt' (Barclay); 'Bumper' (Makhteshim-Agan); 'Juno' (Milenia); 'Menphis' (Rocca); 'Propivap' (Vapco); mixtures: 'Stereo' (+ cyprodinil) (Syngenta); 'Stratego' (+ trifloxystrobin) (Bayer CropScience)