Dichlorprop (CHEM000714)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (6)XML
Record Information
Version1.0
Creation Date2009-06-02 21:21:03 UTC
Update Date2016-11-09 01:08:21 UTC
Accession NumberCHEM000714
Identification
Common NameDichlorprop
ClassSmall Molecule
DescriptionDichlorprop is a chlorophenoxy herbicide similar in structure to 2,4-D that is used to kill annual and perennial broadleaf weeds. It is a component of many common weedkillers. About 4 million pounds of dichlorprop are used annually in the United States. (4)
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Ether
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(2,4-Dichlorophenoxy)propionic acidChEBI
2-(2,4-Dichlorophenoxy)propionateGenerator
2,4-DP CPDMeSH
DichloropropMeSH
Dichlorprop, (R)-isomerMeSH
Dichlorprop, (S)-isomerMeSH
2-Methyl-2-(2',4'-dichlorophenoxy)acetic acidMeSH
Dichlorprop, sodium saltMeSH
2-(2,4-Dichlorophenoxy)propanoic acidMeSH
Dichlorprop, (+,-)-isomerMeSH
Dichlorprop, potassium saltMeSH
Chemical FormulaC9H8Cl2O3
Average Molecular Mass235.064 g/mol
Monoisotopic Mass233.985 g/mol
CAS Registry Number120-36-5
IUPAC Name2-(2,4-dichlorophenoxy)propanoic acid
Traditional Name(+,-)-dichlorprop
SMILESCC(OC1=CC=C(Cl)C=C1Cl)C(O)=O
InChI IdentifierInChI=1S/C9H8Cl2O3/c1-5(9(12)13)14-8-3-2-6(10)4-7(8)11/h2-5H,1H3,(H,12,13)
InChI KeyMZHCENGPTKEIGP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2-phenoxypropionic acids. These are aromatic compounds hat contain a phenol ether attached to the C2-atom of a phenylpropionic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub Class2-phenoxypropionic acids
Direct Parent2-phenoxypropionic acids
Alternative Parents
Substituents
  • 2-phenoxypropionic acid
  • Phenoxyacetate
  • Phenoxy compound
  • Phenol ether
  • 1,3-dichlorobenzene
  • Alkyl aryl ether
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organochloride
  • Organic oxide
  • Organohalogen compound
  • Hydrocarbon derivative
  • 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 Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point122°C
Boiling PointNot Available
Solubility0.35 mg/mL at 20°C [WORTHING,CR & WALKER,SB (1987)]
Predicted Properties
PropertyValueSource
Water Solubility0.38 g/LALOGPS
logP3.13ALOGPS
logP3.07ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)2.95ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity52.71 m³·mol⁻¹ChemAxon
Polarizability20.91 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-3900000000-8c34b228fd37a85535b8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-03di-0900000000-0bc46b559148e22b319eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-03di-0900000000-98157a7e40d20e0cc425Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-03di-0900000000-f62223c14a643777c106Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-03di-0900000000-85339d24500504db1216Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-03k9-2900000000-433a8fa2b5be5d869bafSpectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-03k9-1900000000-c28d310a891e98419d3aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-03di-0900000000-b028c8fd701fd204d081Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-03di-0900000000-e9b0d6314e8f95d8097fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-03di-0900000000-d838e2b8d0cfeb83e046Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-03di-0900000000-ef612253eae93e3d704fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-03di-0900000000-0d84de9a0092db340238Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-03di-0900000000-e13a5965f29a56e7ee90Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-03di-0900000000-e8e24b900c37b7dc2b46Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-03di-0900000000-619ce3657149bfea3bb6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0290000000-47f6045622f1b0ed0183Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2930000000-36cb4444e42220d8edadSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-2900000000-dc9e1ef71abf99817bb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0290000000-dd659f39fc34ba438c3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03e9-0940000000-820a445e6d46f09be9d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0900000000-27642267b16dcefc91bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0190000000-9d334d56eabd92b70213Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-939ea75dee09b3cdd6cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-3900000000-dc8501239c432d4713bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03ei-1920000000-8bc044ac57be5ef3bb6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03e9-4900000000-d8c513da7771ff3460e3Spectrum
MSMass Spectrum (Electron Ionization)splash10-03di-1920000000-677b5256e04a2a1174bfSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityCDDs cause their toxic effects by binding to the aryl hydrocarbon receptor and subsequently altering the trascription of certain genes. The affinity for the Ah receptor depends on the structure of the specific CDD. The change in gene expression may result from the direct interaction of the Ah receptor and its heterodimer-forming partner, the aryl hydrocarbon receptor nuclear translocator, with gene regulatory elements or the initiation of a phosphorylation/dephosphorylation cascade that subsequently activates other transcription factors. The affected genes include several oncogenes, growth factors, receptors, hormones, and drug-metabolizing enzymes. The change in transcription/translation of these genes is believed to be the cause of most of the toxic effects of CDDs. This includes 2,3,7,8-tetrachlorodibenzo-p-dioxin's carcinogenicity is thought to be the result of its ability to alter the capacity of both exogenous and endogenous substances to damage the DNA by inducing CYP1A1- and CYP1A2-dependent drug-metabolizing enzymes. (1)
MetabolismCDDs are absorbed through oral, inhalation, and dermal routes of exposure. CDDs are carried in the plasma by serum lipids and lipoproteins, distributing mainly to the liver and adipose tissue. CDDs are very slowly metabolized by the microsomal monooxygenase system to polar metabolites that can undergo conjugation with glucuronic acid and glutathione. They may increase the rate of their own metabolism by inducing CDDs induce both phase I and phase II enzymes. The major routes of excretion of CDDs are the bile and the feces, though smaller amounts are excreted in the urine and via lactation. (1)
Toxicity ValuesLD50: 344 mg/kg (Oral, Rat)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (5)
Uses/SourcesDioxins occur as by-products from the manufacture of organochlorides, the bleaching of paper, chlorination by waste and drinking water treatment plants, municipal solid waste and industrial incinerators, and natural sources such as volcanoes and forest fires. (1, 2)
Minimum Risk LevelNot Available
Health EffectsIt is considered to be a severe eye irritant. There has been concern that chlorophenoxy herbicides including dichlorprop may cause cancer, and in 1987 the International Agency for Research on Cancer (IARC) ranked this class of compounds as group 2B "possibly carcinogenic to humans". The EPA classifies the R-isomer as “Not Likely to be Carcinogenic to Humans.”(4) Exposure to large amounts of CDDs causes chloracne, a severe skin disease with acne-like lesions that occur mainly on the face and upper body. CDDs may also cause liver damage and induce long-term alterations in glucose metabolism and subtle changes in hormonal levels. In addition, studies have shown that CDDs may disrupt the endocrine system and weaken the immune system, as well as cause reproductive damage and birth defects, central and peripheral nervous system pathology, thyroid disorders, endometriosis, and diabetes. 2,3,7,8-Tetrachlorodibenzo-p-dioxin is also a known human carcinogen. (1, 2)
SymptomsIn addition to chloracne, CDD exposure causes skin rashes, discoloration, and excessive body hair. (1)
TreatmentTreatment may include washing any areas of contact, GI decontamination if swallowed, administering an IV and forced alkaline diuresis. (3)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDichlorprop
Chemspider IDNot Available
ChEBI ID75370
PubChem Compound ID8427
Kegg Compound IDC11020
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available