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 |