Basic Info

Common Name2,4-Dichlorophenoxyacetic Acid(F03457)
2D Structure
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.

FRCD IDF03457
CAS Number94-75-7
PubChem CID1486
FormulaC8H6Cl2O3
IUPAC Name

2-(2,4-dichlorophenoxy)acetic acid

InChI Key

OVSKIKFHRZPJSS-UHFFFAOYSA-N

InChI

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

Canonical SMILES

C1=CC(=C(C=C1Cl)Cl)OCC(=O)O

Isomeric SMILES

C1=CC(=C(C=C1Cl)Cl)OCC(=O)O

Wikipedia2,4-Dichlorophenoxyacetic Acid
Synonyms
        
            2,4-dichlorophenoxyacetic acid
        
            94-75-7
        
            2-(2,4-dichlorophenoxy)acetic acid
        
            2,4-D
        
            (2,4-Dichlorophenoxy)acetic acid
        
            Hedonal
        
            Agrotect
        
            Fernesta
        
            Fernimine
        
            Netagrone
        
Classifies
                

                  
                    Pollutant
                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassPhenoxyacetic acid derivatives
Intermediate Tree NodesNot available
Direct ParentChlorophenoxyacetates
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsChlorophenoxyacetate - 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
DescriptionThis compound belongs to the class of organic compounds known as chlorophenoxyacetates. These are compounds containing a phenoxyacetate that carries one or more chlorine atoms on the benzene ring.

Properties

Property NameProperty Value
Molecular Weight221.033
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Complexity186
Monoisotopic Mass219.969
Exact Mass219.969
XLogP2.8
Formal Charge0
Heavy Atom Count13
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.8557
Human Intestinal AbsorptionHIA+0.9816
Caco-2 PermeabilityCaco2+0.6887
P-glycoprotein SubstrateNon-substrate0.7235
P-glycoprotein InhibitorNon-inhibitor0.8575
Non-inhibitor0.9401
Renal Organic Cation TransporterNon-inhibitor0.8826
Distribution
Subcellular localizationMitochondria0.9357
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8190
CYP450 2D6 SubstrateNon-substrate0.9047
CYP450 3A4 SubstrateNon-substrate0.6519
CYP450 1A2 InhibitorNon-inhibitor0.9183
CYP450 2C9 InhibitorNon-inhibitor0.9339
CYP450 2D6 InhibitorNon-inhibitor0.9594
CYP450 2C19 InhibitorNon-inhibitor0.9812
CYP450 3A4 InhibitorNon-inhibitor0.9559
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8594
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9632
Non-inhibitor0.9239
AMES ToxicityNon AMES toxic0.9650
CarcinogensNon-carcinogens0.8398
Fish ToxicityHigh FHMT0.8980
Tetrahymena Pyriformis ToxicityHigh TPT0.9987
Honey Bee ToxicityHigh HBT0.6451
BiodegradationNot ready biodegradable0.6648
Acute Oral ToxicityII0.7505
Carcinogenicity (Three-class)Non-required0.6930

Model Value Unit
Absorption
Aqueous solubility-2.4477LogS
Caco-2 Permeability1.0037LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.7387LD50, mol/kg
Fish Toxicity0.4016pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.8101pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Citrus fruits0110000European Union106/07/2014
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union106/07/2014
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union106/07/2014
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union106/07/2014
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union106/07/2014
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union106/07/2014
Others (2)0110990European Union106/07/2014
Tree nuts0120000European Union0.206/07/2014
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.206/07/2014
Brazil nuts0120020European Union0.206/07/2014
Cashew nuts0120030European Union0.206/07/2014
Chestnuts0120040European Union0.206/07/2014
Coconuts (Areca nuts/betel nuts,)0120050European Union0.206/07/2014
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.206/07/2014
Macadamias0120070European Union0.206/07/2014
Pecans (Hickory nuts,)0120080European Union0.206/07/2014
Jambuls/jambolans (Acerolas/Barbados cherries, Arbutus berries, Camu camus, Carandas, Coco plums, Grumichamas/Brazil cherries, Hog plums/yellow mombins, Java apples, Otaheite gooseberries, Sea grap...0161070European Union0.05*06/07/2014
Others (2)0161990European Union0.05*06/07/2014
Pistachios0120100European Union0.206/07/2014
Walnuts0120110European Union0.206/07/2014

References

TitleJournalDatePubmed ID
Salinity reduces 2,4-D efficacy in Echinochloa crusgalli by affecting redoxbalance, nutrient acquisition, and hormonal regulation.Protoplasma2018 May29151143
Comparison of questionnaire-based estimation of pesticide residue intake fromfruits and vegetables with urinary concentrations of pesticide biomarkers.J Expo Sci Environ Epidemiol2018 Jan28930298
Persistence of auxinic herbicides applied on pasture and toxicity for succeeding crops.An Acad Bras Cienc2018 Apr-Jun29694496
Suitable reference genes for accurate gene expression analysis in Papaver rhoeas under 2,4-D herbicide stress.Pestic Biochem Physiol2017 Nov29183612
Developmental toxicity of 2,4-dichlorophenoxyacetic acid in zebrafish embryos.Chemosphere2017 Mar28002765
Alkyl(C16, C18, C22)trimethylammonium-Based Herbicidal Ionic Liquids.J Agric Food Chem2017 Jan 1827997185
Development of a QuEChERS-Based Method for the Simultaneous Determination ofAcidic Pesticides, Their Esters, and Conjugates Following Alkaline Hydrolysis.J Agric Food Chem2017 Feb 1528099798
The aryloxyalkanoate dioxygenase-12 (AAD-12) protein is not acutely toxic in mice.Food Chem Toxicol2017 Dec29066407
Isolation and Characterization of 2,4-D Butyl Ester Degrading Acinetobacter sp.ZX02 from a Chinese Ginger Cultivated Soil.J Agric Food Chem2017 Aug 3028771369
The influence of chemical protection on the content of heavy metals in wheat(Triticum aestivum L.) growing on the soil enriched with granular sludge.Environ Monit Assess2017 Aug28762146
Screening Auxin Response, In Vitro Culture Aptitude and Susceptibility toAgrobacterium-Mediated Transformation of Italian Commercial Durum WheatVarieties.Molecules2016 Oct 2827801844
Mineralisation and degradation of 2,4-dichlorophenoxyacetic acid dimethylaminesalt in a biobed matrix and in topsoil.Pest Manag Sci2016 Oct26818964
Unravelling the resistance mechanisms to 2,4-D (2,4-dichlorophenoxyacetic acid)in corn poppy (Papaver rhoeas).Pestic Biochem Physiol2016 Oct27742363
Mustard plant ash: a source of micronutrient and an adsorbent for removal of2,4-dichlorophenoxyacetic acid.Environ Sci Pollut Res Int2016 Oct26884245
Spot Spraying Reduces Herbicide Concentrations in Runoff.J Agric Food Chem2016 May 2526479195
Extra virgin olive oil modulates brain docosahexaenoic acid level and oxidativedamage caused by 2,4-Dichlorophenoxyacetic acid in rats.J Food Sci Technol2016 Mar27570270
Production of a toxic metabolite in 2,4-D-resistant GM crop plants.3 Biotech2016 Jun28330152
How benthic diatoms within natural communities respond to eight common herbicides with different modes of action.Sci Total Environ2016 Jul 127037885
The discovery of Arylex™ active and Rinskor™ active: Two novel auxin herbicides.Bioorg Med Chem2016 Feb 126321602
Mechanisms of thaxtomin A-induced root toxicity revealed by a thaxtomin A sensitive Arabidopsis mutant (ucu2-2/gi-2).Plant Cell Rep2016 Feb26518425