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Carbendazim
BCM · MBC · CARBENDAZIN · spin · carbendazime · agrizim · BAVISTIN · carbendazole
Identifikatoren & physikalische Daten
| CAS No. | 10605-21-7 |
|---|---|
| Summenformel | C9H9N3O2 |
| Durchschnittliche Molmasse | 191,19 g/mol |
| Monoisotopische Masse | 191,06947653 g/mol |
| SMILES | COC(=O)Nc1nc2ccccc2[nH]1 |
| InChIKey | TWFZGCMQGLPBSX-UHFFFAOYSA-N |
| PubChem CID | 25429 |
| ChEMBL | CHEMBL70971 |
| ChEBI | CHEBI:3392 |
| EC No. | 234-232-0 |
| DTXSID | DTXSID4024729 |
| Lokaler Name | Carbendazim |
Chemische & physikalische Eigenschaften
| XLogP | 1,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 67 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 222 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Pestizide | Agrochemicals -> Pesticide active substancesActive substance -> EU Pesticides database: Not approvedPesticides -> FungicidesEnvironmental transformation -> Pesticides (parent, predecessor)Pesticides -> Fungicides -> Benzimidazole fungicidesFungicides, Transformation products |
| LogP (Verteilungskoeffizient) | log Kow = 1.521.491.75 |
| Geruch | Odorless /Technical/ |
| Dichte | 1.45 at 68 °F (NTP, 1992) - Denser than waterwill sink1.45 g/cu cm at 25 °C0.27 g/cm³1.4500 |
| Color/Form | White powderCrystalline powderNearly white solid /Technical/Light-gray powderOff-white, crystalline powder |
| Löslichkeit | less than 1 mg/mL at 70 °F (NTP, 1992)Solubility in water at 24 °C: 29 mg/L at pH 48 mg/L at pH 71.49 mg/L at pH 8Soluble in (g/L at 24 °C): dimethylformamide 5, acetone 0.3, ethanol 0.3, chloroform 0.1, ehtyl acetate 0.135, dichlormethane 0.068, benzene 0.036, cyclohexane <0.01, diethyl ether <0.01, hexane 0.0005Xylene: <1 g/100 g at 20 °CCylcohexanone: < 1 g/100 g /Technical grade/Solubility at 20 °C (mg/L): hexane 0.5benzene 36dichloromethane 68ethanol 300dimethylformamide 5000, chloroform 100, acetone 300Slightly soluble in most solventspyridine: soluble1%, clear, very faintly brownish-yellow<0.1 g/100 mL at 21 ºC |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Decomposition | Decomposes at 300 °C.When heated to decomposition it emits toxic fumes of /nitric oxides/.Slowly decomposed in alkaline soln (22 °C): DT50 >350 days (pH 5 and pH 7), 124 days (pH 9).302-307 °C |
| Schmelzpunkt | 576 to 585 °F (decomposes) (NTP, 1992)Decomposes at 300 °CMP: 302-307 °C (decomposes)302 - 307 °C>300 °C (lit.) |
| Dampfdruck | less than 0.000000075 mmHg at 68 °F<0.001 mmHg at 257 °F (NTP, 1992)7.5X10-10 mm Hg at 20 °CVapor pressure at 20 °C: negligible1.5 x 10-4 Pa (25 °C) |
| Physical Description | Carbendazim appears as light gray or beige powder. (NTP, 1992)White to light-gray, odorless solid[HSDB] Powder[MSDSonline]COLOURLESS CRYSTALS OR GREY-TO-WHITE POWDER. |
| Siedepunkt | 326.92°C (rough estimate) |
| Brechungsindex | 1.6500 (estimate) |
| Flammpunkt | 11 °C |
| Lagerbedingungen | -20°C |
| pKa (Säurekonstante) | 4.48(at 25℃) |
| Aggregatzustand | Solid |
| Farbe | White to off-white |
| Biologische Quelle | human |
| Merck | 13,1799 |
| BRN | 649044 |
| Henry-Konstante | 4.7×105 mol/(m3Pa) at 25℃, HSDB (2015) |
| Hauptanwendungen | agriculturecleaning productscosmeticsenvironmentalfood and beveragespersonal care |
| InChI | 1S/C9H9N3O2/c1-14-9(13)12-8-10-6-4-2-3-5-7(6)11-8/h2-5H,1H3,(H2,10,11,12,13) |
| InChIKey | TWFZGCMQGLPBSX-UHFFFAOYSA-N |
| SMILES | COC(=O)Nc1nc2ccccc2[nH]1 |
| LogP (Verteilungskoeffizient) | 1.4-1.5 at 25℃ and pH5-9 |
| CAS Datenbank | 10605-21-7(CAS DataBase Reference) |
| EPA chemische Informationen | Carbendazim (10605-21-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH317: May cause an allergic skin reaction [Warning Sensitization, Skin]P203, P261, P272, P273, P280, P302+P352, P318, P321, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.3% (2 of 692) of reports.H317 (27.9%): May cause an allergic skin reaction [Warning Sensitization, Skin] |
|---|---|
| Regulatorische Informationen | Chemical: Carbamic acid, 1H-benzimidazol-2-yl-, methyl esterHazard Traits - GenotoxicityReproductive ToxicityRegulation (EC) No 396/2005 (amended)Carbendazim (MBC) is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)2006/135/EC, 2010/70/EC, 2011/58/EU, Reg (EU) 2015/408, Reg. (EU) 2022/801, Reg. (EU) No 540/2011, Reg. (EU) No 542/2011Status: Active Update: 04-03-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/27856 |
| Weitere Sicherheitsinformationen | IMAP assessments - Carbamic acid, 1H-benzimidazol-2-yl-, methyl ester: Human health tier II assessment |
| DOT-Kennzeichnung | Class 9 |
| Brandgefahren | Literature sources indicate that this chemical is probably nonflammable. (NTP, 1992)Gives off irritating or toxic fumes (or gases) in a fire. |
| Gesundheitsgefahren | ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of NOx. (NTP, 1992) |
| Gefahrenübersicht | Reproductive toxin in animal studies[ICSC] Toxic by ingestion and skin absorptionWorkers may be exposed after inhalation of dust or skin contactMale rats fed 200 mg/kg 5 days/week for 2 weeks have testicular damageRats fed 32 mg/kg for 90 days have liver and kidney damage[HSDB] An irritant[MSDSonline] Induces genetic damage in germ cells of humans or animals (3A)[MAK] |
Anwendungen & Verwendung
Beschreibung
Carbendazim is the degradation product and active ingredient of the carbamate fungicide benomyl. Carbendazim (100 μM) disrupts the growth of S. cerevisiae by inhibiting microtubule polymerization. It impairs meiosis and steroidogenesis in an ex vivo rat model of seminiferous tubules and increases prostate weight in rats when administered at a dose of 100 mg/kg but does not affect other testosterone-dependent or estrogen-dependent tissues.
Verwenden
Carbendazim is the most widely used active ingredient in the benzimidazole class of fungicides. It is a systemic fungicide with both protective and curative activities against a wide range of fungal diseases, especially caused by most Ascomycetes spp. and some Basidiomycetes and Deuteromycetes spp. in a wide variety of crop and ornamental uses.