ContaminantDB: Dicamba

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (5)XML

Record Information

Version

1.0

Creation Date

2009-06-02 22:38:11 UTC

Update Date

2016-11-09 01:08:21 UTC

Accession Number

CHEM000720

Identification

Common Name

Dicamba

Class

Small 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,6-Dichloro-O-anisic acid	ChEBI
3,6-Dichloro-O-anisate	Generator

Chemical Formula

C₈H₆Cl₂O₃

Average Molecular Mass

221.037 g/mol

Monoisotopic Mass

219.969 g/mol

CAS Registry Number

1918-00-9

IUPAC Name

3,6-dichloro-2-methoxybenzoic acid

Traditional Name

dicamba

SMILES

COC1=C(Cl)C=CC(Cl)=C1C(O)=O

InChI Identifier

InChI=1S/C8H6Cl2O3/c1-13-7-5(10)3-2-4(9)6(7)8(11)12/h2-3H,1H3,(H,11,12)

InChI Key

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

O-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 Framework

Aromatic homomonocyclic compounds

External Descriptors

dichlorobenzene (CHEBI:81856 )
methoxybenzoic acid (CHEBI:81856 )
Benzoic acid herbicides (C18597 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	115°C
Boiling Point	Not Available
Solubility	8.31 mg/mL at 25°C [USDA PESTICIDE PROPERTIES DATABASE]

Predicted Properties

Property	Value	Source
Water Solubility	0.44 g/L	ALOGPS
logP	2.65	ALOGPS
logP	2.68	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	2.54	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	49.39 m³·mol⁻¹	ChemAxon
Polarizability	19.06 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0v59-3980000000-0bd605abc160c90f228d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0udi-0090000000-ee3bff58e8450ae6f978	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0udi-0090000000-5c965e5300a84ad69dfc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0udi-0090000000-29b0e184b80838ed9bb8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0udi-0090000000-647bbcbad7ea630a3dbd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0udi-0090000000-ffc652670cf539c2cf31	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-00di-0900000000-ae422dccfd91dfc1861b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-03di-0900000000-ce9e487c39d285dfd379	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-03di-0900000000-da5ca0735c3a473426d2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0udi-0900000000-b366489534e404c10682	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0udi-0090000000-0293ef662265899d26ff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-022i-3900000000-454f9873ef438032c22a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-03k9-0900000000-b98d3537cefd0dc56ae8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00di-0900000000-28afb95419b0374fa4ae	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00di-0900000000-7f60791d1e41822ca9fb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0udi-0900000000-2fd722fcd31d6c9b2139	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-03di-0900000000-7a070b99636431c633a4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-03di-0900000000-e9b0d6314e8f95d8097f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-01f6e8fade64b8ed834e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0190000000-66f15f3794e55195f1fd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00tg-1920000000-4c9316aab2809e8732af	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0290000000-7c34aed41d4faaf91ae7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0930000000-d5e61e601e763150a010	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-1900000000-776d811011123acff4e9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uk9-0090000000-cb49796a90ef01b22f3f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0090000000-65dccf83cd91040e4504	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-3920000000-436e1d08520e089a01a8	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral; inhalation; dermal

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

oral 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 Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Dicamba 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 Level

Not Available

Health Effects

In 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)

Symptoms

Exposing 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)

Treatment

Treatment 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 ID

Not Available

HMDB ID

HMDB0251180

FooDB ID

Not Available

Phenol Explorer ID