Dicofol (CHEM000134)

Record Information
Version1.0
Creation Date2009-03-06 18:58:09 UTC
Update Date2026-08-19 08:30:59 UTC
Accession NumberCHEM000134
Identification
Common NameDicofol
ClassSmall Molecule
Description
Dicofol is an organochlorine pesticide that is chemically related to DDT. Specifically, it is used as a miticide against the red spider mite. Though difocol is not extremely toxic, its use is controverial because one of the intermediates used in its production is DDT. It also may accumulate in the environment and its use is restricted in many areas. (5)
Contaminant Sources
  • Clean Air Act Chemicals
  • EPA Endocrine Screening
  • HPV EPA Chemicals
  • IARC Carcinogens Group 3
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,1-Bis(4-chlorophenyl)-2,2,2-trichloroethanolChEBI
1,1-Bis(p-chlorophenyl)-2,2,2-trichloroethanolChEBI
2,2,2-Trichloro-1,1-bis(p-chlorophenyl)ethanolChEBI
4,4'-Dichloro-alpha-(trichloromethyl)benzhydrolChEBI
4-Chloro-alpha-(4-chlorophenyl)-alpha-(trichloromethyl)benzenemethanolChEBI
AcarinChEBI
Di-(p-chlorophenyl)trichloromethylcarbinolChEBI
DTMCChEBI
KelthaneChEBI
MitiganChEBI
p,p-DicofolChEBI
4,4'-Dichloro-a-(trichloromethyl)benzhydrolGenerator
4,4'-Dichloro-α-(trichloromethyl)benzhydrolGenerator
4-Chloro-a-(4-chlorophenyl)-a-(trichloromethyl)benzenemethanolGenerator
4-Chloro-α-(4-chlorophenyl)-α-(trichloromethyl)benzenemethanolGenerator
KeltaneMeSH
Chemical FormulaC14H9Cl5O
Average Molecular Mass370.486 g/mol
Monoisotopic Mass367.910 g/mol
CAS Registry Number115-32-2
IUPAC Name2,2,2-trichloro-1,1-bis(4-chlorophenyl)ethan-1-ol
Traditional Namedicofol
SMILESOC(C1=CC=C(Cl)C=C1)(C1=CC=C(Cl)C=C1)C(Cl)(Cl)Cl
InChI IdentifierInChI=1S/C14H9Cl5O/c15-11-5-1-9(2-6-11)13(20,14(17,18)19)10-3-7-12(16)8-4-10/h1-8,20H
InChI KeyUOAMTSKGCBMZTC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Tertiary alcohol
  • Halohydrin
  • Chlorohydrin
  • Organochloride
  • Organohalogen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alkyl chloride
  • Alcohol
  • Alkyl halide
  • Organooxygen 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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point77.5°C
Boiling PointNot Available
Solubility0.0008 mg/mL at 25 °C [TOMLIN,C (1997)]
Predicted Properties
PropertyValueSource
Water Solubility0.0001 g/LALOGPS
logP5.59ALOGPS
logP5.56ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)11.03ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity86.81 m³·mol⁻¹ChemAxon
Polarizability33.08 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral(5) ; inhalation (5) ; dermal (5).
Mechanism of ToxicityLike other organochloride pesticides, dicofol is believed to act by at least four mechanisms, possibly all functioning simultaneously. It may reduce potassium transport across the membrane. Dicofol also alters the porous channels through which sodium ions pass. These channels activate (open) normally but are inactivated (closed) slowly, thus interfering with the active transport of sodium out of the nerve axon during repolarization. Dicofol inhibits neuronal adenosine triphosphatases (ATPases), particularly Na+K+-ATPase, and Ca2+-ATPase which play vital roles in neuronal repolarization. Dicofol also inhibits the ability of calmodulin, a calcium mediator in nerves, to transport calcium ions that are essential for the release of neurotransmitters. All these inhibited functions reduce the rate of depolarization and increase the sensitivity of neurons to small stimuli that would not elicit a response in a fully depolarized neuron. Difocol is also an endocrine disruptor and binds both the androgen and estrogen receptor. In addition, it may alter sex hormone metabolism by directly inhibiting cytochrome P-450 19A1. Difocol is able to competitively bind transthyretin, which lowers plasma thyroid hormone levels. (7, 1, 2, 3)
MetabolismDicofol can be absorbed via oral, inhahation, and dermal routes. It is distributed primarily to the adipose tissue, as well as the adrenal glands, thyroid, and liver. Metabolism of dicofol produces the metabolites 4,4'-dichloro-benzophenone and 4,4'-dichlorodicofol. Dicofol and its metabolites are excreted mainly in the faeces. (5, 6)
Toxicity ValuesLD50: 595 mg/kg (Oral, Rat) (9) LD50: 2100 mg/kg (Percutaneous, Rabbit) (8)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (4)
Uses/SourcesDicofol is used as a pesticide on agricultural crops and ornamental plants, as well as for agricultural and domestic buildings for mite control. (5)
Minimum Risk LevelNot Available
Health EffectsDicofol poisoning affects the liver, kidneys and the central nervous system. Very severe cases may result in convulsions, coma, or death from respiratory failure. High doses may also cause reproductive damage. (5)
SymptomsSymptoms exposure include nausea, dizziness, weakness and vomiting. Dermal exposure may cause skin irritation or a rash, and eye contact may cause conjunctivitis. (7, 5)
TreatmentTreatment of dicofol poisoning is mainly symptomatic. Areas of contact should be washed with soap and water, and gastric lavage may be performed if ingested. (6)
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0251207
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDicofol
Chemspider ID7970
ChEBI ID34692
PubChem Compound IDNot Available
Kegg Compound IDC14301
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References