ContaminantDB: Dichlorprop

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (6)XML

Record Information

Version

1.0

Creation Date

2009-06-02 21:21:03 UTC

Update Date

2026-03-25 19:42:34 UTC

Accession Number

CHEM000714

Identification

Common Name

Dichlorprop

Class

Small Molecule

Description

Dichlorprop 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(2,4-Dichlorophenoxy)propionic acid	ChEBI
2-(2,4-Dichlorophenoxy)propionate	Generator
2,4-DP CPD	MeSH
Dichloroprop	MeSH
Dichlorprop, (R)-isomer	MeSH
Dichlorprop, (S)-isomer	MeSH
2-Methyl-2-(2',4'-dichlorophenoxy)acetic acid	MeSH
Dichlorprop, sodium salt	MeSH
2-(2,4-Dichlorophenoxy)propanoic acid	MeSH
Dichlorprop, (+,-)-isomer	MeSH
Dichlorprop, potassium salt	MeSH

Chemical Formula

C₉H₈Cl₂O₃

Average Molecular Mass

235.064 g/mol

Monoisotopic Mass

233.985 g/mol

CAS Registry Number

120-36-5

IUPAC Name

2-(2,4-dichlorophenoxy)propanoic acid

Traditional Name

(+,-)-dichlorprop

SMILES

CC(OC1=CC=C(Cl)C=C1Cl)C(O)=O

InChI Identifier

InChI=1S/C9H8Cl2O3/c1-5(9(12)13)14-8-3-2-6(10)4-7(8)11/h2-5H,1H3,(H,12,13)

InChI Key

MZHCENGPTKEIGP-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

2-phenoxypropionic acids

Direct Parent

2-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 Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:75370 )
monocarboxylic acid (CHEBI:75370 )
dichlorobenzene (CHEBI:75370 )
Auxins (C11020 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

EC 1.11.1.6 (catalase) inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	122°C
Boiling Point	Not Available
Solubility	0.35 mg/mL at 20°C [WORTHING,CR & WALKER,SB (1987)]

Predicted Properties

Property	Value	Source
Water Solubility	0.38 g/L	ALOGPS
logP	3.13	ALOGPS
logP	3.07	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	2.95	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	3	ChemAxon
Refractivity	52.71 m³·mol⁻¹	ChemAxon
Polarizability	20.91 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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	splash10-03di-3900000000-8c34b228fd37a85535b8	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 - 35V, Negative	splash10-03di-0900000000-0bc46b559148e22b319e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-03di-0900000000-98157a7e40d20e0cc425	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-03di-0900000000-f62223c14a643777c106	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-03di-0900000000-85339d24500504db1216	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-03k9-2900000000-433a8fa2b5be5d869baf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-03k9-1900000000-c28d310a891e98419d3a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-03di-0900000000-b028c8fd701fd204d081	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-03di-0900000000-e9b0d6314e8f95d8097f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-03di-0900000000-d838e2b8d0cfeb83e046	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-03di-0900000000-ef612253eae93e3d704f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-03di-0900000000-0d84de9a0092db340238	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-03di-0900000000-e13a5965f29a56e7ee90	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-03di-0900000000-e8e24b900c37b7dc2b46	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-03di-0900000000-619ce3657149bfea3bb6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-0290000000-47f6045622f1b0ed0183	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-2930000000-36cb4444e42220d8edad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-2900000000-dc9e1ef71abf99817bb8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0290000000-dd659f39fc34ba438c3f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03e9-0940000000-820a445e6d46f09be9d8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-0900000000-27642267b16dcefc91bf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-0190000000-9d334d56eabd92b70213	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-939ea75dee09b3cdd6cd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-3900000000-dc8501239c432d4713bb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03ei-1920000000-8bc044ac57be5ef3bb6f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03e9-4900000000-d8c513da7771ff3460e3	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03di-1920000000-677b5256e04a2a1174bf	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

CDDs 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)

Metabolism

CDDs 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 Values

LD50: 344 mg/kg (Oral, Rat)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (5)

Uses/Sources

Dioxins 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 Level

Not Available

Health Effects

It 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)

Symptoms

In addition to chloracne, CDD exposure causes skin rashes, discoloration, and excessive body hair. (1)

Treatment

Treatment may include washing any areas of contact, GI decontamination if swallowed, administering an IV and forced alkaline diuresis. (3)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Dichlorprop

Chemspider ID

Not Available

ChEBI ID

75370

PubChem Compound ID

8427

Kegg Compound ID

C11020

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Dichlorprop (CHEM000714)

Structure for CHEM000714: Dichlorprop