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Pyrimethanil
Pyrimethani · Mytho · SCALA · MYTHOS · Penbotec · Hsdb 6916 · Dynmethanil · PYRIMETHANIL
Identifikatoren & physikalische Daten
| CAS No. | 53112-28-0 |
|---|---|
| Summenformel | C12H13N3 |
| Durchschnittliche Molmasse | 199,25 g/mol |
| Monoisotopische Masse | 199,11094743 g/mol |
| SMILES | Cc1cc(C)nc(Nc2ccccc2)n1 |
| InChIKey | ZLIBICFPKPWGIZ-UHFFFAOYSA-N |
| PubChem CID | 91650 |
| ChEMBL | CHEMBL540677 |
| ChEBI | CHEBI:8674 |
| EC No. | 414-220-3 |
| DTXSID | DTXSID8034877 |
Chemische & physikalische Eigenschaften
| XLogP | 2,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 37,8 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 15 |
| Formalladung | 0 |
| Komplexität | 179 |
| Pestizide | Agrochemicals -> Pesticide active substancesActive substance -> EU Pesticides database: ApprovedPesticides -> FungicidesEnvironmental transformation -> Pesticides (parent, predecessor)Pesticide (Pyrimethanil) -> USDA PDB |
| LogP (Verteilungskoeffizient) | log Kow= 2.84 |
| Dichte | 1.15 g/cu cm @ 20 °C |
| Color/Form | Colorless crystals |
| Löslichkeit | In acetone, 389 g/l @ 20 °Cethyl acetate, 617 g/l @ 20 °Cmethanol, 176 g/l @ 20 °Cmethylene chloride, 1000 g/l @ 20 °Cn-hexane, 23.7 g/l @ 20 °Ctoluene, 412 g/l @ 20 °C.In water, 0.121 g/l @ 25 °C.121 mg/L @ 25 °C (exp)DMSO: 130 mg/mL (652.45 mM)0.121 g/L (25 ºC) |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Schmelzpunkt | 96.3 °C88 - 89 °C96°C |
| Dampfdruck | 0.0000165 [mmHg]1.65X10-5 mm Hg @ 25 °C2.2 x l0-5 Pa (25 °C) |
| Physical Description | White solid[Merck Index] Colorless solid[HSDB] Faintly yellow powder[MSDSonline] |
| Stability/Shelf Life | Stable in water within the relevant pH range. Stable for 14 days at 54 °C. |
| Ionization Efficiency | Positive3.782.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| Dissociation Constants | pKa (conjugate acid)= 3.52 |
| Siedepunkt | 362.8±45.0 °C(Predicted) |
| Lagerbedingungen | Keep in dark place,Inert atmosphere,Room temperature |
| pKa (Säurekonstante) | 3.52 |
| Aggregatzustand | Solid |
| Farbe | White to off-white |
| BRN | 151589 |
| Henry-Konstante | 3.4×102 mol/(m3Pa) at 25℃, Feigenbrugel and Calvé (2021) |
| Hauptanwendungen | agricultureenvironmental |
| InChI | InChI=1S/C12H13N3/c1-9-8-10(2)14-12(13-9)15-11-6-4-3-5-7-11/h3-8H,1-2H3,(H,13,14,15) |
| InChIKey | ZLIBICFPKPWGIZ-UHFFFAOYSA-N |
| SMILES | C1(NC2=CC=CC=C2)=NC(C)=CC(C)=N1 |
| CAS Datenbank | 53112-28-0(CAS DataBase Reference) |
| EPA chemische Informationen | Pyrimethanil (53112-28-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]P273, P391, and P501 (click each P-code to see the statement)H411 (100%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]Aggregated GHS information provided per 141 reports by companies from 1 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Commission Regulation (EC) No 451/2000Pyrimethanil is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)Reg. (EU) 2026/372, 2006/74/EC, Reg (EU) 2020/421, Reg (EU) 2026/355 , Reg. (EU) 2018/524, Reg. (EU) 2019/168, Reg. (EU) 2021/566, Reg. (EU) 2022/378, Reg. (EU) 2023/689, Reg. (EU) 2025/99, Reg. (EU) No 540/2011, Reg. (EU) No 678/2014REACH registered substance: 2-anilino-4,6-dimethylpyrimidine (EC: 414-220-3)Pyrimethanil: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| Gefahrenübersicht | May cause irritation[MSDSonline] See Cyprodinil. |
| Special Reports | Hurley PM et alMode of carcinogenic action of pesticides inducing thyroid follicular cell tumors in rodentsEnvironmental Health Perspectives 106 (8): 437-45 (1998). Of 240 pesticides screened for carcinogenicity by the US Environmental Protection Agency Office of Pesticide Programs, at least 24 (10%) produce thyroid follicular cell tumors in rodents. Thirteen of the thyroid carcinogens also induce liver tumors, mainly in mice, and 9 chemicals produce tumors at other sites. |
| Hazard Classes and Categories | Aquatic Chronic 2 (100%)Hazardous to the aquatic environment (chronic) - category 2Aquatic Chronic 2 |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
Anwendungen & Verwendung
Verwenden
Pyrimethanil is a broad spectrum anilino-pyrimidine foliar fungicide. Pyrimethanil functions by inhibiting the biosynthesis of methionine in Botrytis cinerea.
Herstellung & Synthese
synthetische
Pyrimethanil is produced by reaction of 2-bromo-4,6-dimethylpyrimidine with aniline.