Dicamba (CHEM000720)

Record Information
Version1.0
Creation Date2009-06-02 22:38:11 UTC
Update Date2026-08-24 21:49:30 UTC
Accession NumberCHEM000720
Identification
Common NameDicamba
ClassSmall Molecule
Description
Dicamba is an herbicide used to control annual and perennial broadleaf weeds in grain crops and grasslands, and it is used to control brush and bracken in pastures. It will kill broadleaf weeds before and after they sprout. Legumes will be killed by dicamba. In combination with a phenoxyalkanoic acid or other herbicide, dicamba is used in pastures, range land, and non-crop areas (fence-rows, roadways and wastage) to control weeds. Brand names for formulations of this herbicide include Banvel, Oracle and Vanquish. (2)
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Aromatic Hydrocarbon
  • Herbicide
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,6-Dichloro-O-anisic acidChEBI
3,6-Dichloro-O-anisateGenerator
Chemical FormulaC8H6Cl2O3
Average Molecular Mass221.037 g/mol
Monoisotopic Mass219.969 g/mol
CAS Registry Number1918-00-9
IUPAC Name3,6-dichloro-2-methoxybenzoic acid
Traditional Namedicamba
SMILESCOC1=C(Cl)C=CC(Cl)=C1C(O)=O
InChI IdentifierInChI=1S/C8H6Cl2O3/c1-13-7-5(10)3-2-4(9)6(7)8(11)12/h2-3H,1H3,(H,11,12)
InChI KeyIWEDIXLBFLAXBO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as o-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 2 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentO-methoxybenzoic acids and derivatives
Alternative Parents
Substituents
  • 2,5-dichlorobenzoic acid
  • O-methoxybenzoic acid or derivatives
  • 2-halobenzoic acid or derivatives
  • 3-halobenzoic acid or derivatives
  • Halobenzoic acid or derivatives
  • Halobenzoic acid
  • 3-halobenzoic acid
  • 2-halobenzoic acid
  • Benzoic acid
  • Phenoxy compound
  • 1,4-dichlorobenzene
  • Benzoyl
  • Anisole
  • Phenol ether
  • 1-carboxy-2-haloaromatic compound
  • Methoxybenzene
  • Alkyl aryl ether
  • Halobenzene
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Vinylogous halide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Ether
  • Organohalogen compound
  • Organochloride
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • 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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point115°C
Boiling PointNot Available
Solubility8.31 mg/mL at 25°C [USDA PESTICIDE PROPERTIES DATABASE]
Predicted Properties
PropertyValueSource
Water Solubility0.44 g/LALOGPS
logP2.65ALOGPS
logP2.68ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)2.54ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.39 m³·mol⁻¹ChemAxon
Polarizability19.06 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral; inhalation; dermal
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity Valuesoral LD50 in rats: 757 mg/kg body weight, dermal LD50 in rats: >2,000 mg/kg, inhalation LC50 in rats: >200 mg/L (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesDicamba is an herbicide. Dicamba controls annual and perennial rose weeds in grain crops and highlands, and it is used to control brush and bracken in pastures, as well as legumes and cacti. (2)
Minimum Risk LevelNot Available
Health EffectsIn oral, dermal, and inhaled routes of exposure, dicamba has a low acute toxicity. Dicamba may have irritating or corrosive effects on the skin and eyes. The EPA has identified dicamba as a developmental toxin in the Toxics Release Inventory. (3)
SymptomsExposing the skin and eyes to dicamba can cause redness, pain, and blurred vision. The inhalation of dicamba may cause coughing, labored breathing, vomiting, and weakness. Nausea and convulsions may also result from ingestion. (3)
TreatmentTreatment may include washing any areas of contact, GI decontamination if swallowed, administering an IV and forced alkaline diuresis. (1)
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0251180
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDicamba
Chemspider ID2922
ChEBI ID81856
PubChem Compound IDNot Available
Kegg Compound IDC18597
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23726069
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24351123
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24420721