1-(2-(Allyloxy)-2-(2,4-dichlorphe-nyl)ethyl)-1H-imidazol
ENILCONAZOLE · Eniloconazol · ENICONAZOLE · DECCOZIL · FUNGAFLOR · chloramizole · 1-[2-(2,4-dichlorophenyl)-2-prop-2-enoxyethyl]imidazole · MAZAL
Identifikatoren & physikalische Daten
| CAS No. | 35554-44-0 |
|---|---|
| Summenformel | C14H14Cl2N2O |
| Durchschnittliche Molmasse | 297,2 g/mol |
| Monoisotopische Masse | 296,0483185 g/mol |
| SMILES | C=CCOC(Cn1ccnc1)c1ccc(Cl)cc1Cl |
| InChIKey | PZBPKYOVPCNPJY-UHFFFAOYSA-N |
| PubChem CID | 37175 |
| ChEMBL | CHEMBL356918 |
| ChEBI | CHEBI:83829 |
| EC No. | 252-615-0 |
| DTXSID | DTXSID8024151 |
| Lokaler Name | 1-(2-(Allyloxy)-2-(2,4-dichlorphe-nyl)ethyl)-1H-imidazol |
Chemische & physikalische Eigenschaften
| XLogP | 3,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 27,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 19 |
| Formalladung | 0 |
| Komplexität | 291 |
| LogP (Verteilungskoeffizient) | log Kow = 3.82 (pH 9.2 buffer)4.56 |
| Dichte | 1.348 g/ml at 26 °CRelative density (water = 1): 1.2 |
| Color/Form | Slightly yellow to brown crystalline mass.Solidified oilBrownish oil |
| Löslichkeit | In acetone, dichloromethane, ethanol, methanol, isopropanol, xylene, toluene, benzene > 500g/L at 20 °C. In hexane 19 g/L at 20 °C. Also soluble in heptane and petroleum ether.In water, 0.18 g/L at pH 7.6, 20 °C180 mg/L @ 20 °C (exp)Solubility in water, g/100ml at 20 °C: 0.14Chloroform: Slightly SolubleMethanol: Slightly Soluble0.018 g/100 mL |
| Flammpunkt | 192 °C |
| Siedepunkt | 347 °C347.00 °C. @ 760.00 mm Hg319-347 °C (estimated)>340°C |
| Decomposition | When heated to decomposition it emits toxic fumes of /hydrogen chloride and nitrogen oxides/.The substance decomposes on distillation or on burning producing toxic fumes of nitrogen oxides and chloride. |
| Schmelzpunkt | 52.7 °C50 °C52.7°C |
| Dampfdruck | 0.00000119 [mmHg]1.2X10-6 mm Hg at 20 °CVapor pressure at 20 °C: negligible1.58 x l0-4 Pa (20 °C) |
| Brechungsindex | Index of refraction = 1.5643 at 20 °C/D1.5680 (estimate) |
| Physical Description | Imazalil is a slightly yellow to brown solidified oil. Non-corrosive. Used as a fungicide.[Merck Index] Light yellow to brown solid (solidified oil)[ICSC]LIGHT YELLOW-TO-BROWN CRYSTALLINE MASS (SOLIDIFIED OIL). |
| Stability/Shelf Life | Very stable to hydrolysis in dilute acids and alkalis at room temperature, in the absence of light. Stable to temperatures up to 285 °C. Stable to light under normal storage conditions.... Chemically stable at room temperature in the absence of light and stable at temperatures less than about 285 degrees C. |
| Lagerbedingungen | 2-8°C |
| pKa (Säurekonstante) | 6.53 (weak base) |
| Aggregatzustand | Solid |
| Farbe | Light yellow to yellow |
| Merck | 13,3616 |
| BRN | 545683 |
| Henry-Konstante | 3.8×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| Hauptanwendungen | agricultureenvironmental |
| InChI | 1S/C14H14Cl2N2O/c1-2-7-19-14(9-18-6-5-17-10-18)12-4-3-11(15)8-13(12)16/h2-6,8,10,14H,1,7,9H2 |
| InChIKey | PZBPKYOVPCNPJY-UHFFFAOYSA-N |
| SMILES | Clc1ccc(C(Cn2ccnc2)OCC=C)c(Cl)c1 |
| LogP (Verteilungskoeffizient) | 3.820 |
| CAS Datenbank | 35554-44-0(CAS DataBase Reference) |
| NIST chemische Informationen | Imazalil(35554-44-0) |
| EPA chemische Informationen | Imazalil (35554-44-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]H332: Harmful if inhaled [Warning Acute toxicity, inhalation]H351: Suspected of causing cancer [Warning Carcinogenicity]H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]P203, P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P304+P340, P305+P354+P338, P317, P318, P321, P330, P391, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Hazard Traits - CarcinogenicityAuthoritative List - Prop 65Report - regardless of intended function of ingredient in the productCommission Regulation (EC) No 737/2007Imazalil + sulfate is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)Imazaquin + salts is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)1997/73/EC, 2007/21/EC, 2010/57/EU, Reg. (EU) 2024/2781, Reg. (EU) No 2019/291, Reg. (EU) No 540/2011, Reg. (EU) No 705/2011Imazalil: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - 1H-Imidazole, 1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-: Environment tier I assessmentIMAP assessments - 1H-Imidazole, 1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-: Human health tier I assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Corrosives in contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. For electric vehicles or equipment, ERG Guide 147 (lithium ion or sodium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. (ERG, 2024) |
Anwendungen & Verwendung
Beschreibung
Imazalil is an imidazole fungicide that inhibits ergosterol biosynthesis. Imazalil inhibits the growth of various fungi in vitro including P. italicum, A. niger, U. maydis, B. alii, and C. cucumerinum in a pH-dependent manner (MICs = 0.005-2 μg/ml at pH 7). It inhibits S. cerevisiae, but not rat liver microsomal, cytochrome P450 enzymes (CYPs; IC50s = 0.088 and 80 μM, respectively), as well as aromatase CYP19 from human placental microsomes (IC50 = 0.34 μM). Imazalil activates the murine pregnane X receptor (PXR) in a concentration-dependent manner in a cell-based reporter assay. It increases hepatic CYP3A11 and CYP2B10 mRNA levels in mice when administered at a dose of 100 mg/kg. Imazalil also increases Ki-67-positive nuclei in liver sections and hepatic MCM2 mRNA levels, markers of cell proliferation, in mice when co-administered with the murine constitutive androstane receptor (mCAR) agonist TCPOBOP . Formulations containing imazalil have been used to control fungal infection in agriculture.
Verwenden
Imazalil is a systemic fungicide with protective and curative action. It is used for the control of a wide range of fungal diseases on fruit, vegetables and ornamentals, powdery mildew on roses and storage diseases of citrus fruit, pome fruit, bananas and seed potatoes. It is also used as a seed dressing, for control of diseases of cereals (particularly Fusarium and Helminthosporium spp.), and it is particularly active against benzimidazole-resistant strains of plant-pathogenic fungi.