2,4-Dichlorophenoxyacetic Acid
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Basic Info
Common Name | 2,4-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 ID | F03457 |
CAS Number | 94-75-7 |
PubChem CID | 1486 |
Formula | C8H6Cl2O3 |
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 |
Wikipedia | 2,4-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 Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Benzenoids |
Class | Benzene and substituted derivatives |
Subclass | Phenoxyacetic acid derivatives |
Intermediate Tree Nodes | Not available |
Direct Parent | Chlorophenoxyacetates |
Alternative Parents | |
Molecular Framework | Aromatic homomonocyclic compounds |
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 |
Description | This 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 Name | Property Value |
---|---|
Molecular Weight | 221.033 |
Hydrogen Bond Donor Count | 1 |
Hydrogen Bond Acceptor Count | 3 |
Rotatable Bond Count | 3 |
Complexity | 186 |
Monoisotopic Mass | 219.969 |
Exact Mass | 219.969 |
XLogP | 2.8 |
Formal Charge | 0 |
Heavy Atom Count | 13 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.8557 |
Human Intestinal Absorption | HIA+ | 0.9816 |
Caco-2 Permeability | Caco2+ | 0.6887 |
P-glycoprotein Substrate | Non-substrate | 0.7235 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.8575 |
Non-inhibitor | 0.9401 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.8826 |
Distribution | ||
Subcellular localization | Mitochondria | 0.9357 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8190 |
CYP450 2D6 Substrate | Non-substrate | 0.9047 |
CYP450 3A4 Substrate | Non-substrate | 0.6519 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.9183 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9339 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9594 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.9812 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9559 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8594 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9632 |
Non-inhibitor | 0.9239 | |
AMES Toxicity | Non AMES toxic | 0.9650 |
Carcinogens | Non-carcinogens | 0.8398 |
Fish Toxicity | High FHMT | 0.8980 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9987 |
Honey Bee Toxicity | High HBT | 0.6451 |
Biodegradation | Not ready biodegradable | 0.6648 |
Acute Oral Toxicity | II | 0.7505 |
Carcinogenicity (Three-class) | Non-required | 0.6930 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -2.4477 | LogS |
Caco-2 Permeability | 1.0037 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 2.7387 | LD50, mol/kg |
Fish Toxicity | 0.4016 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | 0.8101 | pIGC50, ug/L |
MRLs
Food | Product Code | Country | MRLs | Application Date | Notes |
---|---|---|---|---|---|
Citrus fruits | 0110000 | European Union | 1 | 06/07/2014 | |
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 1 | 06/07/2014 | |
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 1 | 06/07/2014 | |
Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 1 | 06/07/2014 | |
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 1 | 06/07/2014 | |
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 1 | 06/07/2014 | |
Others (2) | 0110990 | European Union | 1 | 06/07/2014 | |
Tree nuts | 0120000 | European Union | 0.2 | 06/07/2014 | |
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.2 | 06/07/2014 | |
Brazil nuts | 0120020 | European Union | 0.2 | 06/07/2014 | |
Cashew nuts | 0120030 | European Union | 0.2 | 06/07/2014 | |
Chestnuts | 0120040 | European Union | 0.2 | 06/07/2014 | |
Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.2 | 06/07/2014 | |
Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.2 | 06/07/2014 | |
Macadamias | 0120070 | European Union | 0.2 | 06/07/2014 | |
Pecans (Hickory nuts,) | 0120080 | European Union | 0.2 | 06/07/2014 | |
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... | 0161070 | European Union | 0.05* | 06/07/2014 | |
Others (2) | 0161990 | European Union | 0.05* | 06/07/2014 | |
Pistachios | 0120100 | European Union | 0.2 | 06/07/2014 | |
Walnuts | 0120110 | European Union | 0.2 | 06/07/2014 |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Salinity reduces 2,4-D efficacy in Echinochloa crusgalli by affecting redoxbalance, nutrient acquisition, and hormonal regulation. | Protoplasma | 2018 May | 29151143 |
Comparison of questionnaire-based estimation of pesticide residue intake fromfruits and vegetables with urinary concentrations of pesticide biomarkers. | J Expo Sci Environ Epidemiol | 2018 Jan | 28930298 |
Persistence of auxinic herbicides applied on pasture and toxicity for succeeding crops. | An Acad Bras Cienc | 2018 Apr-Jun | 29694496 |
Suitable reference genes for accurate gene expression analysis in Papaver rhoeas under 2,4-D herbicide stress. | Pestic Biochem Physiol | 2017 Nov | 29183612 |
Developmental toxicity of 2,4-dichlorophenoxyacetic acid in zebrafish embryos. | Chemosphere | 2017 Mar | 28002765 |
Alkyl(C16, C18, C22)trimethylammonium-Based Herbicidal Ionic Liquids. | J Agric Food Chem | 2017 Jan 18 | 27997185 |
Development of a QuEChERS-Based Method for the Simultaneous Determination ofAcidic Pesticides, Their Esters, and Conjugates Following Alkaline Hydrolysis. | J Agric Food Chem | 2017 Feb 15 | 28099798 |
The aryloxyalkanoate dioxygenase-12 (AAD-12) protein is not acutely toxic in mice. | Food Chem Toxicol | 2017 Dec | 29066407 |
Isolation and Characterization of 2,4-D Butyl Ester Degrading Acinetobacter sp.ZX02 from a Chinese Ginger Cultivated Soil. | J Agric Food Chem | 2017 Aug 30 | 28771369 |
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 Assess | 2017 Aug | 28762146 |
Screening Auxin Response, In Vitro Culture Aptitude and Susceptibility toAgrobacterium-Mediated Transformation of Italian Commercial Durum WheatVarieties. | Molecules | 2016 Oct 28 | 27801844 |
Mineralisation and degradation of 2,4-dichlorophenoxyacetic acid dimethylaminesalt in a biobed matrix and in topsoil. | Pest Manag Sci | 2016 Oct | 26818964 |
Unravelling the resistance mechanisms to 2,4-D (2,4-dichlorophenoxyacetic acid)in corn poppy (Papaver rhoeas). | Pestic Biochem Physiol | 2016 Oct | 27742363 |
Mustard plant ash: a source of micronutrient and an adsorbent for removal of2,4-dichlorophenoxyacetic acid. | Environ Sci Pollut Res Int | 2016 Oct | 26884245 |
Spot Spraying Reduces Herbicide Concentrations in Runoff. | J Agric Food Chem | 2016 May 25 | 26479195 |
Extra virgin olive oil modulates brain docosahexaenoic acid level and oxidativedamage caused by 2,4-Dichlorophenoxyacetic acid in rats. | J Food Sci Technol | 2016 Mar | 27570270 |
Production of a toxic metabolite in 2,4-D-resistant GM crop plants. | 3 Biotech | 2016 Jun | 28330152 |
How benthic diatoms within natural communities respond to eight common herbicides with different modes of action. | Sci Total Environ | 2016 Jul 1 | 27037885 |
The discovery of Arylex™ active and Rinskor™ active: Two novel auxin herbicides. | Bioorg Med Chem | 2016 Feb 1 | 26321602 |
Mechanisms of thaxtomin A-induced root toxicity revealed by a thaxtomin A sensitive Arabidopsis mutant (ucu2-2/gi-2). | Plant Cell Rep | 2016 Feb | 26518425 |