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Grundinformationen
- Standard-SMILES
CC(C)(C)C(O)C(Oc1ccc(-c2ccccc2)cc1)n1cncn1- InChIKey
VGPIBGGRCVEHQZ-UHFFFAOYSA-N- Summenformel
- C20H23N3O2
- Durchschnittliche Molmasse
- 337,423 g/mol
- Monoisotopische Masse
- 337,17902698
Namen und Bezeichner
- Bevorzugter Name
- Bitertanol
- IUPAC
- 1-[([1,1'-Biphenyl]-4-yl)oxy]-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
- Englischer Name
- Bitertanol
- Summenformel
- C20H23N3O2
- Molmasse
- 337.42
Namen und Synonyme
Datenbank-Bezeichner
- CAS
55179-31-2、70585-36-3- PubChem CID
- 91656
- DTXSID
DTXSID2037502- ChEMBL
CHEMBL1566634- ChEBI
CHEBI:83851- EC Number
- 259-513-5
- Nikkaji
- J11.455C
Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 49 · 49-50°C
- Siedepunkt
- 350 °C · 350°C
- Dichte
- 1.1676 · 1.1676 (rough estimate)
- Dampfdruck
- 2.2 x · A 2.2 x l0-10 (20 °C) B 2.5 x l0-9 (20 °C)
- Brechungsindex
- 1.62 · 1.6200 (estimate)
- Flammpunkt
- 100 °C · 100 °C
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- Chloroform: slightl soluble,DMSO: Slightly Soluble,Methanol: Slightly Soluble
- Wasserlöslichkeit
- 2.7 mg · A 2.7 mg l-1 (20 °C) B 1.1 mg l-1 (20 °C)
- pka
- 13.4 · 13.40±0.20(Predicted)
- Merck
- 13 · 13,1301
- BRN
- 620948 · 620948
- Henry's Law Constant
- 1.2 · 1.2×104 mol/(m3Pa) at 25℃, Mackay et al. (2006)
- InChI
- InChI=1S/C20H23N3O2/c1-20(2,3)18(24)19(23-14-21-13-22-23)25-17-11-9-16(10-12-17)15-7-5-4-6-8-15/h4-14,18-19,24H,1-3H3
- InChIKey
- VGPIBGGRCVEHQZ-UHFFFAOYSA-N
- SMILES
- C(N1N=CN=C1)(C(O)C(C)(C)C)OC1C=CC(C2C=CC=CC=2)=CC=1
- NIST chemische Informationen
- 1 H-1,2,4-triazole-1-ethanol, · 1H-1,2,4-triazole-1-ethanol, «beta»-([1,1'-biphenyl]-4-yloxy)-«alpha»-(1,1-dimethylethyl)-(55179-31-2)
- EPA chemische Informationen
- Bitertanol (55179-31-2)
Sicherheit und Regulatorisches
Sicherheitsdaten
- wgk
- 2
- ridadr
- UN 2811
- RTECS-Nr.
- XZ4803050
- risk_code
- 22-23
- Toxizität
- LD50 in rats, male and female mice (mg/kg): >5000, 4488, 4202 orally (Brandes)
- hazard_code
- T
- safety_code
- 45
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 Oral
Chemie und Industrie
Anwendungen
BeschreibungBitertanol is a broad-spectrum triazole fungicide that is active against a variety of fungi, including V. inaequalis and V. pirina, which are responsible for apple and pear scab, respectively, as well as S. mors-uvae and P. ribis, which are responsible for American gooseberry mildew and leaf spot in black currants, respectively. It is active against isolates of V. inaequalis (MICs = 0.6 and 1 μg/ml) but repeated use leads to resistance and cross-resistance (MICs = 9.8-13 μg/ml for bitertanol-resistant isolates). Bitertanol inhibits the cytochrome P450 (CYP450) isoform CYP3A4 (IC50 = 2.74 μM) and inhibits androgenic activity induced by the androgen receptor agonist DHT in a yeast two-hybrid assay (IC50 = 79.85 μM). In rats, bitertanol (10-300 mg/kg, i.p.) increases operant responding on one- and five-minute fixed interval schedules with no effect on motor activity.
VerwendenBitertanol is a foliar-applied triazole fungicide used to protect tropical and subtropical crops in agriculture, in particular bananas. Bitertanol has effects on behavior that are similar to those of psychomotor stimulants.
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