114369-43-6

Basic information

• Product Name: FENBUCONAZOLE
• Synonyms: 1H-1,2,4-Triazole-1-propanenitrile, .alpha.-2-(4-chlorophenyl)ethyl-.alpha.-phenyl-;4-(4-Chlorophenyl)-2-phenyl-2-(1H-1,2,4-tri-azole-1-ylmethyl)butyronitrile;aplha-[2-(4-Chlorophenyl)ethyl]-alpha-phenyl-1H-1,2,4-triazole-1-propanenitrile;Fenbuconazole [iso];Fenbuconazole 100mg [114369-43-6];Fenbuconazol solution;Indar 5;ENABLE(R)
• CAS NO: 114369-43-6
• Molecular Formula: C₁₉H₁₇ClN₄
• Molecular Weight: 336.82
• EINECS: 406-140-2
• Product Categories: Alpha sort;ConazolesPesticides&Metabolites;E-GAlphabetic;F;FA - FL;Fungicides;Pesticides;ConazolesAlphabetic
• Mol File: 114369-43-6.mol

Chemical Properties

• Melting Point: 125.0℃
• Boiling Point: 507.14°C (rough estimate)
• Flash Point: 284.2°C
• Appearance: /
• Density: 1.1288 (rough estimate)
• Vapor Pressure: 5.43E-12mmHg at 25°C
• Refractive Index: 1.6110 (estimate)
• Storage Temp.: 0-6°C
• PKA: 2.34±0.10(Predicted)
• Water Solubility: 0.2 mg l-1 (25 °C)
• BRN: 8333667
• CAS DataBase Reference: FENBUCONAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: FENBUCONAZOLE(114369-43-6)
• EPA Substance Registry System: FENBUCONAZOLE(114369-43-6)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 2
• RTECS: XZ5257500
• Hazardous Substances Data: 114369-43-6(Hazardous Substances Data)

Usage

Metabolic pathway

A number of sites in the fenbuconazole molecule are susceptible to enzymic attack. Consequently, a large variety of metabolites may be formed by oxidative attack on the phenolic rings or the aliphatic benzylic carbon atom adjacent to the 4-chlorophenyl ring. In mammals, oxidation at the benzylic carbon atom is an important pathway, which gives rise to the corresponding alcohol or ketone. This pathway also leads to lactone formation via hydrolysis of the nitrile group and elimination of a molecule of water. The alcohol may also form conjugates with glucuronic or sulfuric acid. Additional reactions in mammals involve hydroxylation of the phenolic rings. In plants, oxidation at the benzylic carbon is an important step to further metabolites and cleavage of the linkage to the triazole ring generates triazole, which is subsequently incorporated in a number of metabolic products. Information presented in this entry is based on the PSD Evaluation (PSD, 1995).

Degradation

Fenbuconazole is thermally stable up to 150 °C and there was no observed degradation when fenbuconazole was incubated in the dark in aqueous solutions at pH 5,7 and 9 for up to 30 days at 25 °C. When an aqueous solution of fenbuconazole (concentration 1.5μg ml-1, pH 7) was irradiated with a xenon arc lamp (filtered to remove wavelengths below 290 nm), the overall radioactivity was 105% of the original amount and the only compound detected was fenbuconazole.

InChI:InChI=1/C19H17ClN4/c20-18-8-6-16(7-9-18)10-11-19(12-21,13-24-15-22-14-23-24)17-4-2-1-3-5-17/h1-9,14-15H,10-11,13H2

Relevant articles and documents

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.

Fungicidal mixtures

A fungicidal mixture containing a) the oxime ether carboxamide of the formula I STR1 and b) an azole derivative II selected from the group of compounds II.1 to II.16 1-[(2RS,4RS;2RS,4SR)-4-bromo-2-(2,4-dichlorophenyl)tetra-hydrofuryl]-1H-1,2,4-triazole (II.1) 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (II.2) (±)-4-chloro-4-[4-methyl-2-(1H-1,2,4-triazol-1-yl-methyl)-1,3-dioxolan-2-yl]phenyl 4-chlorophenyl ether (II.3) (E)-(R,S)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol (II.4) (Z)-2-(1H-1,2,4-triazol-1-ylmethyl)-2-(4-fluorophenyl)-3-(2-chlorophenyl)oxirane (II.5) 4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazolyl methyl)butyronitrile (II.6) 3-(2,4-dichlorophenyl)-6-fluoro-2-(1H-1,2,4-triazol-1-yl)quinazolin-4(3H)-one (II.7) bis(4-fluorophenyl)(methyl)(1H-1,2,4-triazol-1-yl-methyl)silane (II.8) (R,S)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-l-yl)-hexan-2-ol (II.9) (1RS,5RS;1RS,5SR)-5-(4-chlorobenzyl)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (II.10) N-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]-imidazole-1-carboxamide (II.11) (±)-1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole (II.12) (R,S)-1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol (II.13) (±)-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl) propyl 1,1,2,2-tetrafluoroethyl ether (II.14) (E)-1-[1-[[4-chloro-2-(trifluoromethyl)phenyl]imino]-2-propoxyethyl]-1H-imidazole (II.15) and (RS)-2,4'-difluoro-α-(1H-1,2,4-triazol-1-yl-methyl)benzhydryl alcohol (II.16) in a synergistically active amount is described.

Alpha-aryl-alpha-phenylethyl-1H-1,2,4-triazole-1-propanenitriles

This invention relates to substituted and unsubstituted alpha-aryl-alpha-phenylethyl-1H-1,2,4-triazole-1-propanenitriles, their enantiomorphs, acid addition salts and metal salt complexes. These compounds, enantiomorphs, salts and complexes are highly act

Use of certain triazoles to protect materials from fungal attack, articles and compositions

Specific triazoles discovered to be useful as fungicides are: 1. α-n-butyl -α-phenyl-1H-1,2,4-triazole-1-propanenitrile 2. α,α-diphenyl-1H-1,2,4-triazole-1-propanenitrile 3. α-benzyl-α-phenyl-1H-1,2,4-triazole-1-propanenitrile 4. α-n-butyl-α-2-methoxyphenyl-1H-1,2,4-triazole-1-propanenitrile 5. α-n-butyl-α-4-fluorophenyl-1H-1,2,4-triazole-1-propanenitrile 6. α-phenyl-α-(2-phenylethyl)-1H-1,2,4-triazole-1-propanenitrile 7. α-(4-fluorophenyl)-α-n-propyl-1H-1,2,4-triazole-1-propanenitrile 8. α- [2-(4-chlorophenyl)ethyl]-α-phenyl-1H-1,2,4-triazole-1- propanenitrile 9. α-n-butyl-α-4-chlorophenyl-1H-1,2,4-triazole-1-propanenitrile The materials which the fungicidal triazoles are capable of protecting include, for example, wood, fabric, leather, coatings, and caulks. Especially when wood is being protected from attack by fungi we prefer compositions comprising the triazole(s) and a quaternary ammonium compound