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Record Information
Version2.0
Creation Date2009-06-02 22:38:11 UTC
Update Date2014-12-24 20:22:51 UTC
Accession NumberT3D0807
Identification
Common NameDicamba
ClassSmall Molecule
DescriptionDicamba 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)
Compound Type
  • Amine
  • Aromatic Hydrocarbon
  • Herbicide
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
2,5-Dichloro-6-methoxybenzoic acid
2-Methoxy-3,6-dichlorobenzoic acid
3,6-Dichloor-2-methoxy-benzoeizuur
3,6-Dichlor-3-methoxy-benzoesaeure
3,6-Dichloro-2-methoxybenzoic acid
Acido (3,6-dicloro-2-metossi)-benzoico
Banex
Banlen
Banvel
Banvel 4S
Banvel 4ws
Banvel CST
Banvel d
Banvel herbicide
Banvel II herbicide
Brush buster
Compound b dicamba
Dianat
Dianate
Dicambe
Fallowmaster
Kyselina 3,6-dichlor-2-methoxybenzoova
MDBA
Mediben
Metambane
Tracker
Trooper
Velsicol 58-CS-11
Velsicol compound "r"
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 KeyInChIKey=IWEDIXLBFLAXBO-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]
LogPNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-01f6e8fade64b8ed834eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0190000000-66f15f3794e55195f1fdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00tg-1920000000-4c9316aab2809e8732afJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0290000000-7c34aed41d4faaf91ae7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0930000000-d5e61e601e763150a010JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-1900000000-776d811011123acff4e9JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-00di-3920000000-436e1d08520e089a01a8JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
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)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound IDNot Available
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDD003996
Stitch IDDicamba
PDB IDNot Available
ACToR ID6347
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D0807.pdf
General References
  1. US Environmental Protection Agency (2009). Recognition and Management of Pesticide Poisonings. [Link]
  2. Wikipedia. Dicamba. Last Updated 9 May 2009. [Link]
  3. Toxipedia: Dicamba [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
  2. Luft S, Milki E, Glustrom E, Ampiah-Bonney R, O'Hara P. Binding of Organochloride and Pyrethroid Pesticides To Estrogen Receptors α and β: A Fluorescence Polarization Assay. Biophysical Journal 2009;96(3):444a.
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
Gene Name:
ESR2
Uniprot ID:
Q92731
Molecular Weight:
59215.765 Da
References
  1. Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
  2. Luft S, Milki E, Glustrom E, Ampiah-Bonney R, O'Hara P. Binding of Organochloride and Pyrethroid Pesticides To Estrogen Receptors α and β: A Fluorescence Polarization Assay. Biophysical Journal 2009;96(3):444a.
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. Involved in the clearance of bile acids and organic anions from the liver.
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular Weight:
76447.99 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.02 uMCLZD_SLCO1B1_24CellzDirect
AC500.02 uMCLZD_SLCO1B1_24CellzDirect
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Zinc ion binding
Specific Function:
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth. Involved in chromatin remodeling. May play a negative role in adipogenesis through the regulation of lipolytic and antilipogenic genes expression.
Gene Name:
NR3C1
Uniprot ID:
P04150
Molecular Weight:
85658.57 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.06 uMTox21_GR_BLA_Agonist_ratioTox21/NCGC
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Urokinase plasminogen activator receptor activity
Specific Function:
Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form.
Gene Name:
PLAUR
Uniprot ID:
Q03405
Molecular Weight:
36977.62 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC501.48 uMBSK_BE3C_uPAR_upBioSeek
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]