Record Information
Version1.0
Creation Date2009-06-22 16:08:28 UTC
Update Date2026-03-26 23:56:41 UTC
Accession NumberCHEM001456
Identification
Common NameChlorothalonil
ClassSmall Molecule
DescriptionChlorothalonil is a chemical compound of cyanide and a non-systemic fungicide. Chlorothalonil-containing products are sold under the names Bravo, Echo, and Daconil. It is used predominantly on peanuts, potatoes, and tomatoes. It is also used on golf courses and lawns and as an additive in some paints. (4)
Contaminant Sources
  • Clean Air Act Chemicals
  • EPA Endocrine Screening
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Cyanide Compound
  • Household Toxin
  • Nitrile
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
1,3-DicyanotetrachlorobenzeneChEBI
2,4,5,6-Tetrachloro-3-cyanobenzonitrileChEBI
DaconilChEBI
m-TCPNChEBI
m-TetrachlorophthalonitrileChEBI
Meta-TCPNChEBI
Meta-tetrachlorophthalodinitrileChEBI
TetrachloroisophthalonitrileChEBI
TPNChEBI
BravoMeSH
HydroxychlorothalonilMeSH
Chemical FormulaC8Cl4N2
Average Molecular Mass265.911 g/mol
Monoisotopic Mass263.882 g/mol
CAS Registry Number1897-45-6
IUPAC Nametetrachlorobenzene-1,3-dicarbonitrile
Traditional Namechlorothalonil
SMILESClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl
InChI IdentifierInChI=1S/C8Cl4N2/c9-5-3(1-13)6(10)8(12)7(11)4(5)2-14
InChI KeyCRQQGFGUEAVUIL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzonitriles
Direct ParentBenzonitriles
Alternative Parents
Substituents
  • Benzonitrile
  • Halobenzene
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Nitrile
  • Carbonitrile
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point250°C
Boiling Point350°C (760 mmHg)
Solubility0.00081 mg/mL at 25°C [TOMLIN,C (2003)]
Predicted Properties
PropertyValueSource
Water Solubility0.018 g/LALOGPS
logP3.98ALOGPS
logP4.1ChemAxon
logS-4.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area47.58 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity56.72 m³·mol⁻¹ChemAxon
Polarizability21.31 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-0090000000-d566d379b31b52559e5eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-aaee35a70f1d90febbb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0090000000-aaee35a70f1d90febbb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0090000000-aaee35a70f1d90febbb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-5d7f1c0e056f6eeed4feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0090000000-5d7f1c0e056f6eeed4feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0090000000-5d7f1c0e056f6eeed4feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-61a9942377c137649544Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0090000000-61a9942377c137649544Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0090000000-61a9942377c137649544Spectrum
MSMass Spectrum (Electron Ionization)splash10-02t9-1390000000-74d812beaa5ccd60e60bSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (1) ; inhalation (1) ; dermal (1)
Mechanism of ToxicityOrganic 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. (2)
MetabolismOrganic 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. (1)
Toxicity ValuesLD50: 2500 mg/kg (Intraperitoneal, Mouse) (5) LD50: 3700 mg/kg (Oral, Mouse) (5) LD50: >2500 mg/kg (Dermal, Rat) (5) LC50: 310 mg/m3 over 1 hour (Inhalation, Rat) (5)
Lethal Dose216 to 300 milligrams for an adult human (cyanide salts). (6)
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (3)
Uses/SourcesChlorothalonil is a non-systemic fungicide. It is used predominantly on peanuts, potatoes, and tomatoes. It is also used on golf courses and lawns and as an additive in some paints. (4)
Minimum Risk LevelNot Available
Health EffectsExposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (1, 2)
SymptomsCyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (1, 2)
TreatmentAntidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (2)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0250125
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkChlorothalonil
Chemspider ID13861400
ChEBI ID3639
PubChem Compound ID15910
Kegg Compound IDC11037
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11016668
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=14575671
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17482661
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23116300
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23866729
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24455968
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24984836
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24990551