Basic information
- CAS
55179-31-2- Standard SMILES
CC(C)(C)C(O)C(Oc1ccc(-c2ccccc2)cc1)n1cncn1- InChIKey
VGPIBGGRCVEHQZ-UHFFFAOYSA-N- Molecular formula
- C20H23N3O2
- Average molar mass
- 337.4 g/mol
- Monoisotopic mass
- 337.17902698
Overview
1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol is a member of the class of triazoles that is 3,3-dimethyl-1-(1,2,4-triazol-1-yl)butane-1,2-diol substituted at position O-1 by a biphenyl-4-yl group. It is a member of biphenyls, an aromatic ether, a secondary alcohol and a member of triazoles.
Names & identifiers
- Preferred name
- Bitertanol
- IUPAC
- 3,3-dimethyl-1-(4-phenylphenoxy)-1-(1,2,4-triazol-1-yl)butan-2-ol
- English name
- Bitertanol
- Molecular formula
- C20H23N3O2
- Molecular weight
- 337.42
Names & synonyms
Bitertanol55179-31-2BaycorBiloxazolBaycor 25 WP3,3-dimethyl-1-(4-phenylphenoxy)-1-(1,2,4-triazol-1-yl)butan-2-olBay KWG 0599KWG 0599DTXSID2037502GR7Z3Z59G9DTXCID00175021-(4-Phenylphenoxy)-1-(1,2,4-triazole-1)-3,3-dimethylbutan-2-ol
Show more names
kwg0599SIBUTOLR 33986Baycoral(1RS,2RSBiloxuronBAYMAT(R)AI3-27699
1H-1,2,4-Triazole-1-ethanol, beta-((1,1'-biphenyl)-4-yloxy)-alpha-(1,1-dimethylethyl)-beta-((1,1'-Biphenyl)-4-yloxy)-alpha-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanolRefChem:569582BAY KWG-0599CHEBI:3130KWG-05991-(4-biphenylyloxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol259-513-5
Database identifiers
- CAS
55179-31-2、70585-36-3- PubChem CID
- 91656
- DTXSID
DTXSID2037502- ChEMBL
CHEMBL1566634
Properties
Computed structural properties
- XLogP
- 4.2
- Topological polar surface area
- 60.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 6
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 398
Experimental & physicochemical properties
Pesticides
Fungicides
Active substance -> EU Pesticides database: Not approved
Pesticides -> Fungicides
Environmental transformation -> Pesticides (parent, predecessor)
Pesticide (Bitertanol) -> USDA PDB
LogP4.1
Endocrine DisruptorsPotential endocrine disrupting compound
Vapor Pressure0.0000075 [mmHg]
Physical DescriptionColorless solid; [Merck Index] Colorless crystalline solid with an aromatic odor; [AccuStandard MSDS]
Ionization Efficiency
Positive
2.83
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
Physicochemical properties
- Melting point
- 49 · 49-50°C
- Boiling point
- 350 °C · 350°C
Safety & regulation
GHS classification
GHS Classification
Danger
H302 (84.3%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P264, P270, P271, P284, P301+P317, P304+P340, P316, P320, P330, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 51 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
H401: Toxic to aquatic life [Hazardous to the aquatic environment, acute hazard]
P273, P391, and P501 (click each P-code to see the statement)
Hazard information
Regulatory Information
Commission Regulation (EC) No 33/2008
Bitertanol is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
2008/934, Reg. (EU) No 1278/2011, Reg. (EU) No 767/2013
Bitertanol: HSNO Approval: HSR003369 Approved with controls
Other Safety InformationIMAP assessments - 1H-1,2,4-Triazole-1-ethanol, .beta.-([1,1'-biphenyl]-4-yloxy)-.alpha.-(1,1-dimethylethyl)-: Environment tier I assessment
Hazards SummaryThe commercial product is a mixture of diastereomers; [Merck Index] Developmental toxicity studies in rats and rabbits showed malformations and post-implantation loss at doses at or above those maternally toxic; [Reference #1]
Hazard Classes and Categories
Acute Tox. 4 (84.3%)
Reproductive toxicity - Category 2
Hazardous to the aquatic environment (Acute) - Category 2
Toxicology
Toxicity DataLC50 (rat) > 717 mg/m3/1hr
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationChemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc.
Uses & manufacturing
Uses
Used as post-emergence fungicide for bananas and plantains; [Reference #1]
Not registered for use in the US; Tolerances for imported bananas and plantains; [Reference #1]
Farming (Pesticides) [Category: Industry]
Use ClassificationEnvironmental transformation -> Pesticides (parent, predecessor)
Applications
DescriptionBitertanol 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.
UsesBitertanol is used as a seed treatment on winter wheat and barley and as a foliar treatment to control diseases on bananas, ornamentals, fruit and vegetables.
UsesAgricultural fungicide.
UsesBitertanol 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.
Related reactions
4 records
Compound notes
Loading…