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Cyproconazole 766 Cyproconazole CYPROCONAZOLE (239) First draft prepared by Mr S Funk, United States Environmental Protection Agency, Washington DC, USA EXPLANATION Cyproconazole is an azole fungicide used to control a wide range of fungi on cereal crops, coffee, sugar beet, fruit trees, grapes, including rust on cereal crops, powdery mildew on cereal crops, fruit tree and grapes, and scab on apple. It is both a prevention and treatment fungicide. At the 41st session of the CCPR (2009), it was scheduled for the evaluation as a new compound by the 2010 JMPR. The residue studies were submitted by the manufacturer for support of the following commodities: almond, apple, barley, bean, maize, oat, pea, peanut, rice, sugar beet, soya bean, and wheat. GAP information was also submitted by Japan and the Netherlands. IDENTITY ISO Common Name Cyproconazole Chemical name: IUPAC (2RS,3RS;2SR,3SR)-2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4- triazol-1-yl)butan-2-ol CA alpha-(4-chlorophenyl)-alpha-(1-cyclopropyl-ethyl)-1H-1,2,4-triazole-1- ethanol CAS No 94361-06-5 Manufacturers code No. SAN619 Structural formula N N OH N Cl Molecular formula C15H18ClN3O Molecular mass 291.8 Stereochemistry: Cyproconazole possesses two chiral carbon atoms (C2 and C3 of the butane backbone) indicated in the structure with asterisks: Cyproconazole 767 * N N * N OH Cl This structure exists in four stereoisomeric forms: two enantiomeric pairs of diastereoisomers. The following are defined: “Diastereomer A”: enantiomeric pair, where the 3-hydroxy group and 2-hydrogen are located on the same side. “Diastereomer B”: enantiomeric pair, where the 3-hydroxy group and 2-hydrogen are located on opposite sides. H H N N N N N N OH OH Cl Cl (2S, 3S)-isomer (2R, 3R)-isomer Diastereomers H H N N N N N N OH OH Cl Cl (2R, 3S)-isomer (2S, 3R)-isomer Enantiomers Cyproconazole is an approximately 1:1 mixture of the two diastereomers, each of which is exactly a 1:1 mixture of the enantiomers. All four stereoisomers are present in similar amounts. PHYSICAL AND CHEMICAL PROPERTIES Method Property Results Reference Test material Melting point 106.2–106.9 °C SAN619 pure ai Das, 1998 (99.7%) SAN619/0447 OECD 102 Boiling point Thermal decomposition starts at about 300 °C before the SAN619 pure ai Das, 2000 boiling point is reached, and oxidative decomposition starts (99.7%) SAN619/6876 at about 115 °C OECD 103 768 Cyproconazole Method Property Results Reference Test material Temperature of Oxidative decomposition starts at about 115 °C, followed SAN619 pure ai Das, 2000 decomposition or by thermal decomposition which starts at about 300 °C (99.7%) SAN619/6876 sublimation OECD 103 Cyproconazole shows neither without nor with air any peak Angly, 2000 between room temperature and the melting point (approx. SAN619 tech. ai SAN619/6950 98 °C) (96.6%) OECD 113 Relative density 1.25–103 kg / m3 at 22 °C corresponding to a relative SAN619 pure ai Füldner, 1998 density of 1.25 (99.7%) SAN619/0503 OECD 109 Vapour pressure Vapour pressure curve in the solid state: SAN619 pure ai Widmer, 1998 10log P [Pa] = - 5868.9 1 / T K + 15.097 (99.7%) SAN619/0532 from fit of measurements between 45 and 75 °C OECD 104 vapour pressure at 25 °C : 2.610-5 Pa Volatility Henry’s law constant at 25 °C : calculation Burkhard, 1999 5.010-5 Pa m³/mol SAN619/0099 Physical state Pure active substance: white fine powder SAN619 pure ai Das, 1999a and colour (99.7%) SAN619/6781 Technical grade active substance: beige fine powder visual SAN619 tech. ai Das, 1999b (96.6%) SAN619/6780 visual Odour Pure active substance: odourless SAN619 pure ai Das, 1999a (99.7%) SAN619/6781 Technical grade active substance: weak aromatic organoleptic SAN619 tech. ai Das, 1999b (96.6%) SAN619/6780 organoleptic Spectra active UV Absorption Characteristics : OECD 101 Oggenfuss, 2001 substance The molar extinction were determined to be: SAN619 pure ai SAN619/7060 solution wavelength [nm] molar (99.7%) extinction coefficient [mol-1 cm-1] neutral 222 11515 266 233 acidic 222 12211 266 250 basic 222 10283 266 238 No absorption maximum between 350 nm and 750 nm was observed. Spectra of None of the impurities present in the active substance as impurities manufactured are of toxicological or environmental significance Solubility in The solubility of cyproconazole in buffer solutions was CIPAC MT 157.2 Wisson, 1989 water including determined to be : corresponding to effect of pH 108 8 mg/L at pH 4.1 and 22 °C OECD 105 SAN619/6125 93 18 mg/L at pH 7.1 and 22 °C SAN619 pure 109 4 mg/L at pH 10.0 and 22 °C (98.9%) Solubility in The solubility in different organic solvents at 25 °C was organic solvents determined to be : CIPAC MT 157.3 Stulz, 1998a acetone 360 g/L SAN619 tech. dichloromethane 430 g/L (96.6%) SAN619/0522 ethyl acetate 240 g/L hexane 1.3 g/L methanol 410 g/L octanol 100 g/L toluene 100 g/L Partition The octanol / water partition coefficient (Pow) and its OECD 107 Stulz, 1998b coefficient logarithm to base 10 (log Pow) was determined to be: SAN619 pure SAN619/0518 n-octanol / water Pow = 1200 ± 61 log Pow = 3.1 (99.7%) Cyproconazole 769 Method Property Results Reference Test material Hydrolysis rate Cyproconazole was hydrolytically stable at pH 4, 5, 7 and 9 OECD 111 Glänzel, 1999 at 50 °C for 5 days. The ratios of the two isomers remained 14C labelled SAN619/6849 unchanged. SAN619, (98.9% radio-chemical purity) Photochemical The molar extinction coefficients in aqueous buffer OECD 101 Oggenfuss, 2000 degradation solutions at pH 5, 7 and 9 are below 10 l mol-1 cm-1 SAN619 pure SAN619/7018 Therefore the investigation of photochemical degradation is (99.7%) not required Dissociation Cyproconazole does not have a dissociation constant within OECD 112 Gampp, 1989 constant the range 3 to 10 SAN619 pure SAN619/6138 (98.9%) Stability in air, Based on the calculation according to Atkinson the calculation Glänzel, 1996 photo-chem. estimated half-life of cyproconazole in the atmosphere by according to SAN619/5173 degradation, hydroxyl radical oxidation is Atkinson breakdown 0.661 days product(s) (1.5 · 106 OH-radicals / cm³ and a 12 hour day) Flammability Cyproconazole is not considered highly flammable EEC A.10 v. Helvoirt, SAN619 tech. 1994 (95.0%) SAN619/6239 Auto- Cyproconazole shows no self-ignition EEC A.16 v. Helvoirt, flammability SAN619 tech. 1995 (95.0%) SAN619/6240 Flash point Not required, cyproconazole, is a solid with a melting point > 40 °C Explosive Cyproconazole is not considered an explosive in accordance EEC A.14 Krips, 1996 properties with EEC Method A.14 SAN619 tech. SAN619/5160 (95.7%) Surface tension Surface tension of aqueous suspensions at 20 °C by the OECD 115 Martin, 1999 Wilhelmy plate method was determined to be : SAN619 tech. = 65.2 mN / m (at 90% of the saturation (96.6%) SAN619/6767 concentration) Cyproconazole has to be regarded as a surface active substance because the surface tension is lower than 60 mN/m Oxidizing Cyproconazole is not considered an oxidizing substance EEC A.17 Krips, 1995 properties SAN619 tech. (95.0%) SAN619/6238 FORMULATIONS Formulation a Active Ingredient Content WG 300 g/kg WG 100 g/kg WG 160 g/kg WG 400 g/kg SL 100 g/L SL 50 g/L EC 240 g/L SC 400 g/L FU 1 g/part a EC - emulsifiable concentrate, FU - smoke generator ; SC - suspension concentrate; SL - soluble concentrate; WG - wettable granule Additionally there are numerous co-formulations with imazalil, difenoconazole, prochloraz, propiconazole, chlorothalonil, cyprodinil, fludioxonil, azoxystrobin, and copper. 770 Cyproconazole Specification An FAO specification for cyproconazole has not been established by the JMPS under the new system. METABOLISM AND ENVIRONMENTAL FATE Metabolites are given various abbreviations and code numbers in the studies. Abbreviations and codes, chemical names, and structures are shown below, along with information on the matrices in which the particular chemical was found. Parent and metabolites identified in cyproconazole plant and livestock metabolism studies and environmental fate studies Common name/Code Chemical name Chemical structure Matrices Metabolite# Apples, Grapes, and Cl Wheat forage, OH grain and Cyproconazole α-(4-chlorophenyl)-α-(1- straw (CGA 221949) cyclopropylethyl)-1H- N Poultry M1/M2 1,2,4-triazole-1-ethanol N N tissues, H3C eggs and excreta Goat milk and tissues M3/M4 NOA421152 2-(4-chlorophenyl)-3- Rat (faeces, cyclopropyl-1,2-butanediol OH urine) OH Cl Apples, Grapes, and Cl Wheat forage, OH grain and 2-(4-chlorophenyl)-3- M9/M14 straw cyclopropyl-1- NOA 421153 N Poultry [1,2,4]triazol-1-yl-butane- N tissues, 2,3-diol N H C eggs and 3 OH excreta Goat kidney and liver Apples, Cl Grapes, and Wheat OH forage, 3-(4-chlorophenyl)-2- M11/M18 grain and cyclopropyl-4- NOA 421154 N straw [1,2,4]triazol-1-yl-butane- N Poultry 1,3-diol HO N tissues, eggs and excreta Goat liver Cyproconazole 771 Common name/Code Chemical name Chemical structure Matrices Metabolite# Cl OH 3-(4-chlorophenyl)-2- Poultry M10/M10a cyclopropyl-3-hydroxy-4- N excreta, NOA 452154 [1,2,4]triazol-1-yl-butyric N Grapes acid HO N O OH 2-[2-(4-chloro-phenyl)-2- Apples, M13 hydroxy-1-methyl-3- N grapes, NOA451353 [1,2,4]triazol-1-yl-propyl]- N wheat cyclopropanol OH N Cl Apples, Grapes, and Cl Wheat grain and M15 1-(4-chlorophenyl)-2- straw NOA 408616 [1,2,4]triazol-1-yl-ethanol N Poultry N tissues and OH N eggs Soil photolysis Wheat forage and Cl straw Poultry M16 1-(4-chlorophenyl)-2- tissues, CGA 123420 [1,2,4]triazol-1-yl-ethanone N eggs and N excreta O N Soil photolysis OH 3-(4-chloro-phenyl)-2- OH M20 cyclopropyl-4- N Rat NOA452668
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