55179-31-2

Basic information

• Product Name: Bitertanol
• Synonyms: 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;beta-((1,1’-biphenyl)-4-yloxy)-alpha-(1,1-dimethylethyl)-1h-1,2,4-triazole-1;biloxazol;kwg0599;SIBUTOL(R)
• CAS NO: 55179-31-2
• Molecular Formula: C₂₀H₂₃N₃O₂
• Molecular Weight: 337.42
• EINECS: 259-513-5
• Product Categories: Biphenyl & Diphenyl ether;Traizoles;A-BAlphabetic;Alpha sort;B;BI - BZPesticides;Fungicides;Pesticides&Metabolites;Alphabetic;BA - BH;Agro-Products;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 55179-31-2.mol

Chemical Properties

• Melting Point: 49-50°C
• Boiling Point: 350°C
• Flash Point: 100 °C
• Appearance: /
• Density: 1.1676 (rough estimate)
• Vapor Pressure: 1.49E-12mmHg at 25°C
• Refractive Index: 1.6200 (estimate)
• PKA: 13.40±0.20(Predicted)
• Water Solubility: A 2.7 mg l-1 (20 °C) B 1.1 mg l-1 (20 °C)
• Merck: 13,1301
• BRN: 620948
• CAS DataBase Reference: Bitertanol(CAS DataBase Reference)
• NIST Chemistry Reference: Bitertanol(55179-31-2)
• EPA Substance Registry System: Bitertanol(55179-31-2)

Safety Data

• Hazard Codes: T
• Statements: 22-23
• Safety Statements: 45
• RIDADR: UN 2811
• WGK Germany: 2
• RTECS: XZ4803050
• Hazardous Substances Data: 55179-31-2(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Industry:
Bitertanol is used as a foliar-applied fungicide for protecting tropical and subtropical crops, particularly bananas. It is also used as a seed treatment on winter wheat and barley, and as a foliar treatment to control diseases on various crops such as beans, ornamentals, fruit, and vegetables.
Used in Fungicide Applications:
Bitertanol is employed as a fungicide to control a variety of diseases in agricultural settings. It is used for control on prunes when drying and is registered for use in many European, South American, Far Eastern, and African countries, as well as in Australia. More than 20 global suppliers provide Bitertanol for agricultural purposes.

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.

InChI:InChI=1/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

Upstream product

• 555-31-7 aluminum isopropoxide 
• 43121-37-5 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one 

Downstream Products

• 112439-39-1 Toluene-4-sulfonic acid (S)-1-[(R)-(biphenyl-4-yloxy)-[1,2,4]triazol-1-yl-methyl]-2,2-dimethyl-propyl ester 
• 112438-86-5 Toluene-4-sulfonic acid (S)-1-[(S)-(biphenyl-4-yloxy)-[1,2,4]triazol-1-yl-methyl]-2,2-dimethyl-propyl ester 
• 72013-85-5 methoxymethyl-carbamic acid 1-(biphenyl-4-yloxy-[1,2,4]triazol-1-yl-methyl)-2,2-dimethyl-propyl ester 
• 98169-49-4 (+)-bitertanol 
• 98169-49-4 (-)-bitertanol 
• 98169-49-4 (1R,2S)-1-(biphenyl-4-yloxy)-3, 3-dimethyl-1-(1H-1, 2, 4-triazol-1-yl) butan-2-ol 
• 98169-49-4 (1S,2R)-1-(biphenyl-4-yloxy)-3, 3-dimethyl-1-(1H-1, 2, 4-triazol-1-yl) butan-2-ol 
• 98169-49-4 (1R,2R)-1-(biphenyl-4-yloxy)-3, 3-dimethyl-1-(1H-1, 2, 4-triazol-1-yl) butan-2-ol 
• 98169-49-4 (1S,2S)-1-(biphenyl-4-yloxy)-3, 3-dimethyl-1-(1H-1, 2, 4-triazol-1-yl) butan-2-ol 

Relevant articles and documents

Synergistic Combinations Of Active Ingredients

The present invention relates to novel active compound combinations comprising, firstly, at least one known compound of the formula (I) in which R1 and A have the meanings given in the description and, secondly, at least one further known active compound from groups (2) to (27) listed in the description, which combinations are highly suitable for controlling animal pests such as insects and unwanted acarids and also phytopathogenic fungi.

Synergistic Active Compound Combinations Comprising Phenyltriazoles

The present invention relates to novel active compound combinations comprising, firstly, at least one known compound of the formula (I) in which R1 and R2 have the meanings given in the description. and at least one further known active compound from groups (2) to (27) listed in the description, which combinations are highly suitable for controlling animal pests such as insects and unwanted acarids and also phytopathogenic fungi.

Synergistic Fungidical Active Substance Combinations

The present invention relates to novel active substance combinations which contain spiroxamine, which is known, a known azole and a known carboxamide and which are very suitable for controlling undesired phytopathogenic fungi.

SUBSTITUTED SPIROCYCLIC KETOENOLS

The present invention relates to novel substituted spirocyclic ketoenols of the formula (I) in which W, X, Y, Z, A, B, D and G are as defined in the disclosure, to a plurality of processes for their preparation and to their use as pesticides, microbicides and herbicides.

Glyoxyl acid amides, method for producing them and their use for controlling harmful organisms

The invention relates to novel gloyoxylic acid amides, to a process for their preparation and to their use for controlling harmful organisms.

Use of oxabicyclo[2.2.1]heptane derivatives as pesticidal agents

7-oxabicyclo[2.2.1]heptane derivatives of formula (I) in which X, R1, R2, R3 and R4 have the meanings set forth in the specification, are very suitable for controlling undesired microorganisms and animal pests. New 7-oxabicyclo[2.2.1]heptane derivatives of formula (Ia) in which X, R1, R2, R3 and R14 have the meanings set forth in the specification, and a process for the preparation of the new compounds.

Triazolopyrimidines

The invention relates to novel triazolopyrimidines of the formula 1wherein X represents halogen, Y represents a hydrogen atom or halogen, and R has the meanings given in the disclosure, to a process for the preparation of the new compounds, and to their use as microbicides.

Heterocyclic fluoroalkenyl thioethers and the use thereof as pesticides(III)

The present invention relates to novel heterocyclic fluoroalkenyl thioethers of the formula (I) in which X represents hydrogen, halogen or alkyl, m represents integers from 3 to 10, n represents 0, 1 or 2, Y represents sulphur or oxygen, R1 represents halogen, represents in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkenyl, alkenyloxy, alkenylthio or alkylcarbonyl, represents optionally substituted cycloalkyl, represents optionally substituted aryl or represents optionally substituted heterocyclyl and R2 represents hydrogen, halogen, represents in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkenyl, alkenyloxy, alkenylthio or alkylcarbonyl, represents optionally substituted cycloalkyl, represents optionally substituted aryl or represents optionally substituted heterocyclyl, ?except for compounds where R1=alkyl, Y=oxygen and X=hydrogen, and to processes for their preparation and to their use as pesticides.

Heterocyclic fluoroalkenyl thioethers and the use thereof as pesticides (I)

The present invention relates to novel heterocyclic fluoroalkenyl thioethers of the formula (I) in which X represents hydrogen, halogen or alkyl, m represents integers from 2 to 10, n represents 0, 1 or 2, Y represents unsubstituted or substituted methylene and p represents 1, 2 or 3. and to processes for their preparation and to their use as pesticides.

Substituted imide derivatives

The present invention relates to novel substituted imide derivatives of the general formula (I) in which R1 represents optionally substituted cycloalkyl, R2 represents optionally substituted alkyl or optionally substituted cycloalkyl, R3 represents alkyl, alkoxy, alkylthio, amino, alkylamino or dialkylamino and R4 represents cyano or nitro, and to processes for their preparation and to their use for controlling animal pests and as herbicides.