ChemicalBook > CAS DataBase List > Bitertanol

Bitertanol

Product Name: Bitertanol
CAS No.: 55179-31-2
Chemical Name: Bitertanol
Synonyms: BAYCOR;kwg0599;SIBUTOL;R 33986;Baycoral;(1RS,2RS;Biloxuron;biloxazol;BAYMAT(R);AI3-27699
CBNumber: CB8442457
Molecular Formula: C20H23N3O2
Formula Weight: 337.42
MOL File: 55179-31-2.mol

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Bitertanol Property

Melting point:: 49-50°C
Boiling point:: 350°C
Density: 1.1676 (rough estimate)
vapor pressure: A 2.2 x l0^-10 (20 °C) B 2.5 x l0^-9 (20 °C)
refractive index: 1.6200 (estimate)
Flash point:: 100 °C
storage temp.: 2-8°C
solubility: Chloroform: slightl soluble,DMSO: Slightly Soluble,Methanol: Slightly Soluble
Water Solubility: A 2.7 mg l^-1 (20 °C) B 1.1 mg l^-1 (20 °C)
pka: 13.40±0.20(Predicted)
Merck: 13,1301
BRN: 620948
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 Chemistry Reference: 1H-1,2,4-triazole-1-ethanol, «beta»-([1,1'-biphenyl]-4-yloxy)-«alpha»-(1,1-dimethylethyl)-(55179-31-2)
EPA Substance Registry System: Bitertanol (55179-31-2)

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Safety

Hazard Codes: T
Risk Statements: 22-23
Safety Statements: 45
RIDADR: UN 2811
WGK Germany: 2
RTECS: XZ4803050
Toxicity: LD50 in rats, male and female mice (mg/kg): >5000, 4488, 4202 orally (Brandes)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 45349
Product name: Bitertanol
Purity: mixture of diastereo isomers
Packaging: 250mg
Price: $36.5
Updated: 2022/05/15

TCI Chemical

Product number: B6034
Product name: Bitertanol
Packaging: 1G
Price: $129
Updated: 2025/07/31

TCI Chemical

Product number: B6034
Product name: Bitertanol
Packaging: 5G
Price: $385
Updated: 2025/07/31

Cayman Chemical

Product number: 24054
Product name: Bitertanol
Purity: ≥98%
Packaging: 25mg
Price: $48
Updated: 2023/06/20

Cayman Chemical

Product number: 24054
Product name: Bitertanol
Purity: ≥98%
Packaging: 50mg
Price: $90
Updated: 2023/06/20

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Bitertanol Chemical Properties,Usage,Production

Description

Bitertanol 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.

Chemical Properties

White Solid

Uses

Bitertanol 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.

Uses

Agricultural fungicide.

Uses

Bitertanol 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.

Definition

ChEBI: 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 member of triazoles and a secondary alcohol.

Agricultural Uses

Fungicide: A fungicide used to control a variety of diseases. Used as control for prunes when drying. Not currently registered in the U.S. or EU countries (pending). Used in many European, South American, Far Eastern and African countries, a well as in Australia for use on beans (all types) and various ornamentals. More than 20 global suppliers.

Trade name

BAYCOR®; BAY KWG 0599®; BAYMATSPRAY ®; BILOXAZOL®; KWG 0599®; SIBUTOL®, (with Fuberidazole)

Metabolic pathway

Bitertanol is a mixture of two diastereoisomeric pairs and this complicates its metabolism, each biotransfonnation affording a mixture of isomers. Metabolism has been studied under environmental conditions and in plants and mammals. Degradation in soil and sediments is slow and only small quantities of products (other than CO₂ and bound residues) are produced. Most information is available for mammals in which metabolism occurs mainly by oxidative routes followed by conjugation. The information presented below is derived from the UK MAFF Pesticide Safety Directorate (PSD, 1994).

Degradation

The hydrolytic stability of [¹⁴C]bitertanowl as measured at pH 4, 7 and 9 over 30 days at 25 and 40 °C. No decomposition was observed and the DT₅₀ was estimated at >1 year at 25 °C.
Aqueous solutions of [¹⁴C-triazole]-and [¹⁴C-biphenyl]-bitertanol were irradiated for 48 and 72 hours, respectively, using a mercury arc lamp under conditions somewhat exceeding natural sunlight. Calculated DT₅₀ values were 38-52 hours and an estimated environmental DT₅₀ was considered to be 11 days. 4-Hydroxybiphenyl (4) and 1,2,4-triazole (5) were identified as major photolysis products accounting for 12% and 53% of the radioactivity, respectively. These are shown in Scheme 1. At least six minor products were detected but these were not identified.
Very little degradation occurred under soil surface photolysis conditions simulating natural sunlight. No discrete products were detected. Bound residue increased to only 5% of the total over 35 days.

References

[1] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.
[2] P. HILDEBRAND. Resistance of Venturia inaequalis to bitertanol and other demethylation-inhibiting fungicides[J]. Canadian Journal of Plant Pathology-revue Canadienne De Phytopathologie, 1988, 20 1: 311-316. DOI: 10.1080/07060668809501704
[3] XUAN LV . Effects of triazole fungicides on androgenic disruption and CYP3A4 enzyme activity[J]. Environmental Pollution, 2017, 222: Pages 504-512. DOI: 10.1016/j.envpol.2016.11.051
[4] ANGELA R. ALLEN Robert C M. Bitertanol, A triazole fungicide, increases operant responding but not motor activity[J]. Neurotoxicology and teratology, 1993, 15 4: Pages 237-242. DOI: 10.1016/0892-0362(93)90004-8

Bitertanol Preparation Products And Raw materials

Raw materials

Methanol solution Hydrazinium hydroxide solution 1,2,4-Triazole Biphenyl Pinacolone Sodium borohydride Sulfuryl chloride

Preparation Products

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Bitertanol Suppliers

Canada 1 China 108 France 2 Germany 3 India 1 Japan 2 South Korea 1 Switzerland 1 United Kingdom 2 United States 18 Global 139

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View Lastest Price from Bitertanol manufacturers

Hebei Chuanghai Biotechnology Co,.LTD

Product: Bitertanol 55179-31-2
Price: US $10.70/KG
Min. Order: 10KG
Purity: 99%
Supply Ability: 10000kg
Release date: 2024-08-13

55179-31-2, BitertanolRelated Search:

Triadimenol Diethoxydimethylsilane FIREMASTER BP-6 Dimethyl ether N,N-Dimethylformamide Dimethyldimethoxysilane Bifenthrin Bifendate 1H-Benzotriazole Dimethyl sulfate Biphenyl Bifonazole Dimethyl sulfoxide Dimethyl sulfide Dimethyl fumarate ETHANE Dimethyl carbonate 2,3,3',4,4',5-HEXACHLOROBIPHENYL

1-(4-phenylphenoxy)-1-(1,2,4-triazole-1)-3,3-dimethylbutan-2-ol

1h-1,2,4-triazole-1-ethanol,beta-((1,1’-biphenyl)-4-yloxy)-alpha-(1,1-dimethyl

baycor25wp

baymat-spray

3,3-DIMETHYL-1-(4-PHENYLPHENOXY)-1-(1,2,4-TRIAZOL-1-YL)BUTAN-2-OL

1-[（1，1'-biphenyl)-4-yloxyl]-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol

1RS,2RS)-1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1H-1,2,4-triazole-l-yl)butan-2-ol

beta-([1,1'-biphenyl]-4-yloxy)-alpha-tert-butyl-1H-1,2,4-triazol-1-ethanol

b-([1,1'-Biphenyl]-4-yloxy)-a-tert-butyl-1H-1,2,4-triazol-1-ethanol

1-(4-Biphenylyloxy)-3,3-dimethyl-1-(1H-1,2,4-triazole-1-yl)-2-butanol

1-(Biphenyl-4-yloxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol

Baycoral

Biloxuron

ALL-RAC-1-(BIPHENYL-4-YLOXY)-3,3-DIMETHYL-1-(1H-1,2,4-TRIAZOL-1-YL)BUTAN-2-OL

Bitertanol Standard

Bay KWG 0599 (Bayer)

Baycor(Bayer)

BITERTANOL MIXTURE OF DIASTEREOMERS,PEST

BAYCOR, 100MG, NEAT

SS-([1,1'-BIPHENYL]-4-YLOXY)-A-(1,1-DIMETHYLETHYL)-1H-1,2,4-TRIAZOLE-1-ETHANOL

bitertanol (bsi,iso)

(1RS,2RS

(1RS,2RS:1RS,2RS)-1-(BIPHENYL-4-YLOXY)-3,3-DIMETHYL-1-(1H-1,2,4-TRIAZOL-1-YL)BUTAN-2-OL

BITERTANOL;BAYCOR;BILOXAZOL;KWG 0599

beta-((1,1’-biphenyl)-4-yloxy)-alpha-(1,1-dimethylethyl)-1h-1,2,4-triazole-1

biloxazol

kwg0599

BITERTANOL

BETA([1,1'BIPHENYL]-4-YLOXY)-I-(1,1-DIMETHYL-ETHYL)R-1H-1,2,4-TRIAZOLE-1-ETHANOL

BAYCOR (TM)

BAYCOR

BAYMAT(R)

BAY KWG 0599

B-([1,1'-BIPHENYL]-4-YLOXY)-A-(1,1-DIMETHYL-ETHYL)-1H-1,2,4-TRIAZOLE-1-ETHANOL

SIBUTOL(R)

SIBUTOL

1RS,2RS)-1-(Biphenyl-4-yloxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Baycor (TM) 100mg [55179-31-2]

Baycor DC 300

β-([1,1'-Biphenyl]-4-yloxy)-α-(1,1-diMethylethyl)-1H-1,2,4-triazole-1-ethanol

1-([1,1'-biphenyl]-4-yloxy)-3,3-diMethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Bitertanol 1

Bitertanol @100 μg/mL in MeOH

Bitertanol@1000 μg/mL in Acetone

Bitertanol Solution

1H-1,2,4-Triazole-1-ethanol, β-([1,1'-biphenyl]-4-yloxy)-α-(1,1-dimethylethyl)-

55179-31-2 Bitertanol

AI3-27699

Caswell No. 334B

R 33986

Bitertanol Solution in Methanol

Bitertanol in Acetone

Bitertanol in Methanol

Bitertanol 10.0 μg/ml Ethyl acetate

Bitertanol 100 μg/ml Acetonitrile

L10660000ALBitertanoL10μg/mLin Acetonitrile

Bitertanol, 10 mM in DMSO

Bitertanol 10 μg/mL in Acetonitrile