Fenbuconazole
Basic information
- CAS
114369-43-6- Standard SMILES
N#CC(CCc1ccc(Cl)cc1)(Cn1cncn1)c1ccccc1- InChIKey
RQDJADAKIFFEKQ-UHFFFAOYSA-N- Molecular formula
- C19H17ClN4
- Average molar mass
- 336.8 g/mol
- Monoisotopic mass
- 336.11417422
Overview
4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile is a member of the class of triazoles that is 1-chloro-4-(3-phenylpropyl)benzene substituted at position 3 of the propyl moiety by cyano and 1,2,4-triazol-1-ylmethyl groups. It is a nitrile, a member of triazoles and a member of monochlorobenzenes.
Names & identifiers
- Preferred name
- Fenbuconazole
- IUPAC
- 4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile
- English name
- FENBUCONAZOLE
- Molecular formula
- C19H17ClN4
- Molecular weight
- 336.82
Names & synonyms
Fenbuconazole114369-43-6DTXSID8032548P9P3C2AL0Z4-(4-Chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazol-1-ylmethyl)butyronitrileRH-7592alpha-(2-(4-Chlorophenyl)ethyl)-alpha-phenyl-1H-1,2,4-triazole-1-propanenitrileDTXCID60125481H-1,2,4-Triazole-1-propanenitrile, alpha-(2-(4-chlorophenyl)ethyl)-alpha-phenyl-(RS)-4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazol-1-ylmethyl)butyrontrilealpha(2-(4-chlorophenyl)ethyl)-alpha-phenyl-1H-1,2,4-triazole-1-propanentrile1H-1,2,4-Triazole-1-propanenitrile, alpha-[2-(4-chlorophenyl)ethyl]-alpha-phenyl-
Show more names
INDARTROIKArh7592INDAR(R)enitrileGOVERN(R)ENABLE(R)FENETHANIL
4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazol-1-ylmethyl)butanenitrileRefChem:598855CHEBI:81762406-140-2119611-00-6Fenbuconazole [ISO]4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrileFenbuconazol
Properties
Computed structural properties
- XLogP
- 3.2
- Topological polar surface area
- 54.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 6
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 434
Experimental & physicochemical properties
Pesticides
Fungicides
Active substance -> EU Pesticides database: Not approved
Environmental transformation -> Pesticides (parent, predecessor)
Fungicides
Pesticide (Fenbuconazole) -> USDA PDB
LogP3.23
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section
183.9 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID8032548]
182.44 Ų [M+H]+ [CCS Type: TW]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
P273, P391, and P501 (click each P-code to see the statement)
Warning
H373 (94.3%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
P260, P273, P319, P391, and P501 (click each P-code to see the statement)
Hazard information
Regulatory Information
Commission Regulation (EC) No 1490/2002
Fenbuconazole is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
2010/87/EU, Reg. (EU) 2018/155, Reg. (EU) 2022/801, Reg. (EU) No 540/2011
Status: Active Update: 07-09-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/32833
1H-1,2,4-Triazole-1-propanenitrile, .alpha.-2-(4-chlorophenyl)ethyl-.alpha.-phenyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and Categories
Aquatic Acute 1 (100%)
STOT RE 2 (94.3%)
Hazardous to the aquatic environment (acute) - category 1
Carcinogenicity - Category 2
Aquatic Acute 1
Toxicology
Toxicity Summary
Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)
MeSH Pharmacological ClassificationSubstances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Uses & manufacturing
UsesThis is a man-made compound that is used as a pesticide.
Use Classification
Environmental transformation -> Pesticides (parent, predecessor)
Fungicides
Additional notes
DefinitionChEBI: 4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile is a member of the class of triazoles that is 1-chloro-4-(3-phenylpropyl)benzene substituted at position 3 of the propyl moiety by cyano and 1,2,4-triazol-1-ylmethyl groups. It is a member of triazoles, a nitrile and a member of monochlorobenzenes.
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