ContaminantDB: 2,4-Dichlorophenoxyacetic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (9)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:22 UTC

Update Date

2026-03-25 19:42:16 UTC

Accession Number

CHEM000217

Identification

Common Name

2,4-Dichlorophenoxyacetic acid

Class

Small Molecule

Description

2,4-Dichlorophenoxyacetic acid (2,4-D) is a common systemic herbicide used in the control of broadleaf weeds. It is the most widely used herbicide in the world, and the third most commonly used in North America. 2,4-D is also an important synthetic auxin, often used in laboratories for plant research and as a supplement in plant cell culture media such as MS medium. (S685). 2,4-D can be formulated as emulsifiable concentrates, granules, soluble concentrate and solids, water-dispersible granules, and wettable powders. 2,4-D is used alone, but is commonly formulated with dicamba, mecoprop, mecoprop-p, MCPA, and clopyralid. 2,4-D was one of the ingredients in Agent Orange, the herbicide widely used during the Vietnam War. Though 2,4-D composed 50% of Agent Orange, the health effects of Agent Orange are related to dioxin contaminants generated during the production of Agent Orange – not 2,4-D itself. On August 8, 2007, the U.S. Environmental Protection Agency issued a ruling that stated that existing data do not support a link between human cancer and 2,4-D exposure.

Contaminant Sources

Clean Air Act Chemicals
EPA Endocrine Screening
HMDB Contaminants - Urine
HPV EPA Chemicals
IARC Carcinogens Group 2B
STOFF IDENT Compounds
Suspected Compounds – Schymanski Project
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Aromatic Hydrocarbon
Ether
Household Toxin
Industrial/Workplace Toxin
Metabolite
Organic Compound
Organochloride
Pesticide
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2,4-Dichlorphenoxy)essigsaeure	ChEBI
2,4-D acid	ChEBI
2,4-Dichlorophenoxyacetate	ChEBI
2,4-Dichlorphenoxyessigsaeure	ChEBI
Acide 2,4-dichloro phenoxyacetique	ChEBI
Hedonal	ChEBI
Trinoxol	ChEBI
2,4-D	Kegg
(2, 4-Dichlorophenoxy)acetic acid	HMDB
(2,4-Dichloor-fenoxy)-azijnzuur	HMDB
(2,4-Dichlor-phenoxy)-essigsaeure	HMDB
(2,4-Dichlorophenoxy)-acetic acid	HMDB
(2,4-Dichlorophenoxy)acetic acid	HMDB
(2,4-Dichlorophenoxy)acetic acid (acd/name 4.0)	HMDB
(2,4-Dichlorophenyloxy)acetic acid	HMDB
(2,4-Dichlorphenoxy)acetic acid	HMDB
(2,4-Dichlorphenoxy)essigsaure	HMDB
(Dichlorophenoxy)acetic acid	HMDB
2,4-D Mecoprop	HMDB
2,4-Dichlorophenoxyethanoic acid	HMDB
2,4-Dichlorphenoxyessigsaure	HMDB
2,4-Dwuchlorofenoksyoctowy kwas	HMDB
Acido(2,4-dicloro-fenossi)-acetico	HMDB
Acme amine 4	HMDB
Acme butyl ester 4	HMDB
Acme LV 4	HMDB
Agrotect	HMDB
Amidox	HMDB
Aminopielik 50Sl	HMDB
Amoxone	HMDB
Aqua-kleen	HMDB
Atlas D	HMDB
b-Selektonon	HMDB
Barrage HF	HMDB
Brush-rhap	HMDB
Chipco turf herbicide D	HMDB
Chipco turf herbicide quot dquot	HMDB
Chloroxone	HMDB
Crop rider	HMDB
Crotilin	HMDB
Dacamine	HMDB
Debroussaillant 600	HMDB
Decamine	HMDB
Ded-weed	HMDB
Ded-weed LV-69	HMDB
Desormone	HMDB
Dezormon	HMDB
Diclordon	HMDB
Dicopur	HMDB
Dicotox	HMDB
Dinoxol	HMDB
DMA-4	HMDB
Dormone	HMDB
Emulsamine BK	HMDB
Emulsamine e-3	HMDB
Envert 171	HMDB
Envert DT	HMDB
Esteron	HMDB
Esteron 44 weed killer	HMDB
Esteron 76 be	HMDB
Esteron 99	HMDB
Esteron 99 concentrate	HMDB
Esteron brush killer	HMDB
Esterone	HMDB
Esterone four	HMDB
Estone	HMDB
Farmco	HMDB
Fernesta	HMDB
Fernimine	HMDB
Fernoxone	HMDB
Ferxone	HMDB
Foredex 75	HMDB
Formula 40	HMDB
Hedonal (the herbicide)	HMDB
Hedonal, herbicide	HMDB
Herbidal	HMDB
Huragan	HMDB
Ipaner	HMDB
Krotiline	HMDB
Kwas 2,4-dwuchlorofenoksyoctowy	HMDB
Kwasu 2,4-dwuchlorofenoksyoctowego	HMDB
Kyselina 2,4-dichlorfenoxyoctova	HMDB
Lawn-keep	HMDB
Macrondray	HMDB
Miracle	HMDB
Monosan	HMDB
Mota maskros	HMDB
Moxone	HMDB
Netagrone	HMDB
Netagrone 600	HMDB
Pennamine	HMDB
Pennamine D	HMDB
Phenox	HMDB
Pielik	HMDB
Planotox	HMDB
Plantgard	HMDB
RCRA waste number u240	HMDB
Rhodia	HMDB
Salvo	HMDB
Spontox	HMDB
Spritz-hormin/2,4-D	HMDB
Spritz-hormit/2,4-D	HMDB
Super D weedone	HMDB
Superormone concentre	HMDB
Tiller S	HMDB
Transamine	HMDB
Tributon	HMDB
Uniso	HMDB
Vergemaster	HMDB
Verton	HMDB
Verton 2-D	HMDB
Verton 2D	HMDB
Verton D	HMDB
Vertron 2D	HMDB
Vidon 638	HMDB
Visko-rhap	HMDB
Visko-rhap low drift herbicides	HMDB
Visko-rhap low volatile 4l	HMDB
Weed tox	HMDB
Weed-ag-bar	HMDB
Weed-b-gon	HMDB
Weed-rhap	HMDB
Weedar	HMDB
Weedar-64	HMDB
Weedatul	HMDB
Weedez wonder bar	HMDB
Weedone	HMDB
Weedone LV4	HMDB
Weedtrol	HMDB
2,4-Dichlorophenoxyacetic acid, potassium salt	HMDB
2,4-Dichlorophenoxyacetic acid, ammonium salt	HMDB
2,4-Dichlorophenoxyacetic acid, lithium salt	HMDB
2,4-Dichlorophenoxyacetic acid, sodium salt	HMDB
2,4 Dichlorophenoxyacetic acid	HMDB
2,4-Dichlorophenoxyacetic acid	ChEBI

Chemical Formula

C₈H₆Cl₂O₃

Average Molecular Mass

221.037 g/mol

Monoisotopic Mass

219.969 g/mol

CAS Registry Number

94-75-7

IUPAC Name

2-(2,4-dichlorophenoxy)acetic acid

Traditional Name

rhodia

SMILES

OC(=O)COC1=C(Cl)C=C(Cl)C=C1

InChI Identifier

InChI=1S/C8H6Cl2O3/c9-5-1-2-7(6(10)3-5)13-4-8(11)12/h1-3H,4H2,(H,11,12)

InChI Key

OVSKIKFHRZPJSS-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as chlorophenoxyacetates. Chlorophenoxyacetates are compounds containing a phenoxyacetate that carries one or more chlorine atoms on the benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenoxyacetic acid derivatives

Direct Parent

Chlorophenoxyacetates

Alternative Parents

Substituents

Chlorophenoxyacetate
Phenoxy compound
1,3-dichlorobenzene
Phenol ether
Alkyl aryl ether
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organochloride
Organohalogen compound
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dichlorobenzene (CHEBI:28854 )
chlorophenoxyacetic acid (CHEBI:28854 )
Phenoxy herbicides (C03664 )

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 1.1.1.25 (shikimate dehydrogenase) inhibitor

Physical Properties

State

Solid

Appearance

White to yellow powder. (11)

Experimental Properties

Property	Value
Melting Point	140.5°C
Boiling Point	160 °C (0.4 mm Hg)
Solubility	0.677 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	0.55 g/L	ALOGPS
logP	2.82	ALOGPS
logP	2.5	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	2.81	ChemAxon
pKa (Strongest Basic)	-4.9	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	48.22 m³·mol⁻¹	ChemAxon
Polarizability	19.28 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	splash10-008c-5930000000-9e18343a9f7af8f4a0e7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9220000000-a032ac9bac05d35c0263	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-03di-0900000000-c5992eb4929bea0caa6f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-03di-0920000000-3876fd4c2b58b792ae17	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-03di-0900000000-f62223c14a643777c106	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-03di-0900000000-d29595def934a65b4542	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-03di-0900000000-d18ea65f7c9d27efe5a0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-03di-0900000000-12b2f23aca41aae72df5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-03k9-1900000000-a0b74f1e7d9731547b09	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-03di-0910000000-43f63558efefe96b63ae	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-03di-0900000000-be8426feb3ff30050b90	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-03di-0900000000-8d1371b31d25aec0cee0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-03di-0900000000-1256ac189274e190c88c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-03di-0900000000-47d5448d947385bed9c7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-03k9-1900000000-4ec7a7637e246c888d26	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-03di-0900000000-c301b58f9c0c131183b2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-03di-0900000000-6e3b873d7e2075a6278c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-03k9-1900000000-4ec7a7637e246c888d26	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-03di-0900000000-918b0eab0ce642175a9f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-03di-0910000000-929b2d2c324a765328bd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-03di-0900000000-47d5448d947385bed9c7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-65c3456a76900ddcdf95	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-0090000000-a8795ac49517985dafc3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-3930000000-16586343387743da8ed4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0190000000-fb5ffe9f68edbfbd545d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0390000000-c164f3f3990c2d027cdf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fkc-3930000000-173e8bfc603e92ae9c83	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03di-2920000000-124d727a3888770108bf	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (12); inhalation (12); dermal (12)

Mechanism of Toxicity

2,4-Dichlorophenoxyacetic acid is a strong oxidant and is known to cause lipid peroxidation and the generation of free radicals that can modify lipids and proteins. It is also known to inhibit glutathione S transferase which leads to a depletion of ATP, NADPH and glutathione (5, 6). These actions can cause cell toxicity and apopotosis among metabolically active cells. Some of the endocrine effects of 2,4-D may be mediated by the 2,4-D mediated displacement of sex hormones from the sex hormone binding globulin or the 2,4-D mediated blocking or OAT6 transport proteins that are needed for the transport of functional organic ions and dicarboxylates (including estrone sulfate).

Metabolism

Metabolism of 2,4-D is minimal in humans, with nearly all of it excreted unchanged as the parent compound. In particular, 2,4-D is rapidly excreted from the body, primarily in the urine. Much of the compound appears to be eliminated unchanged, although some 2,4-D is eliminated from the body as a conjugate. 2,4-D is metabolized to 2,4-dichlorophenol (2,4-DCP) by cytochrome P450 3A4 (CYP 3A4), the major form of monooxygenase enzyme in the human liver.

Toxicity Values

LD50: 1400 mg/kg (Dermal, Rabbit) (14) LD50: 469 mg/kg (Oral, Guinea pig) LD50: 639 mg/kg (Oral, Rat) (13) LD50: 138 mg/kg (Oral, Mouse) (13)

Lethal Dose

80-800 mg/kg (Oral) (8)

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (10)

Uses/Sources

2,4-D is is an agrochemical - a substance that is used in agriculture or horticulture. It is a broadleaf herbicide, which when sprayed or dusted on plants causes its leaves to fall off, and functions as a synthetic auxin. 2,4-D is commonly found in lawn care products; wheat, corn, and other grass family herbicides; forestry products; treatments for roadside weeds; and aquatic weed control products.

Minimum Risk Level

Not Available

Health Effects

All forms of 2,4-D are considered low in toxicity when absorbed via skin or via inhalation. The acid and salt forms of 2,4-D are highly toxic to eye tissue. Long term chronic exposure to 2,4-D has been linked to non-Hodgkins lymphoma and Parkinson’s disease but these are epidemiological associations only. 2,4-D is also reported to have negative effects on the endocrine system (specifically the thyroid and gonads) and immune system. 2,4-D displaces sex hormones from the protein (sex hormone binding globulin) that normally transports these hormones in the blood. 2,4-D reduces the activity of several proteins important to immune system function. Researchers at NIOSH have demonstrated a decreased production of cells responsible for making antibodies in mice bone marrow, in addition to decreased T-cells, produced in the thymus.

Symptoms

Symptoms of acute oral exposure include vomiting, diarrhea, headache, confusion, aggressive or bizarre behavior, hypotension and muscle twitching. Skeletal muscle injury and renal failure may also occur. Prolonged dermal exposure may include skin irritation, whereas prolonged inhalation exposure may lead to coughing and burning sensations in the upper respiratory tract and chest.

Treatment

The general treatment of acute chlorophenoxy herbicide poisoning consists of decontamination of the gastrointestinal tract, resuscitation and supportive care. For severe, acute oral poisoning by 2,4-D forced alkaline diuresis appears to be most effective (9). Forced alkaline diuresis is often used to increase the excretion of acidic drugs like salicylates and phenobarbitone. For forced alkaline diuresis, a diuretic like furosemide is given intravenously and sodium bicarbonate is added to the infusion fluid to make blood and, in turn, urine alkaline. Potassium replacement becomes of utmost importance during the process because potassium is usually lost in urine. If blood levels of potassium are depleted below normal levels, then hypokalemia occurs, which promotes bicarbonate ion retention and prevents bicarbonate excretion, thus interfering with the alkalinization of the urine.

Concentrations