Details
Stereochemistry | MIXED |
Molecular Formula | C9H21NO3.C8H6Cl2O3 |
Molecular Weight | 412.305 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 0 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(O)CN(CC(C)O)CC(C)O.OC(=O)COC1=C(Cl)C=C(Cl)C=C1
InChI
InChIKey=SRPJGPPDQIFOGY-UHFFFAOYSA-N
InChI=1S/C9H21NO3.C8H6Cl2O3/c1-7(11)4-10(5-8(2)12)6-9(3)13;9-5-1-2-7(6(10)3-5)13-4-8(11)12/h7-9,11-13H,4-6H2,1-3H3;1-3H,4H2,(H,11,12)
2,4-Dichlorophenoxyacetic acid (2,4-D) was the first synthetic herbicide to be commercially developed and has commonly been used as a broadleaf herbicide for over 60 years. It is a selective herbicide that kills dicots without affecting monocots and mimics natural auxin at the molecular level. 2,4-D was developed during World War II as one of many
so-called phenoxy herbicides by aiming to increase crop yields for a nation at war. It was
commercially released in 1946 becoming the first successful selective herbicide and allowed for greatly
enhanced weed control in wheat, maize, rice, and other similar cereal crops because it specifically targets dicots.
This herbicide family is said to have “initiated an agricultural revolution and laid the corner stone of
present-day weed science” when it was first marketed in the 1940s.
Originator
Sources: http://www.toxipedia.org/display/toxipedia/2%2C4-D
Curator's Comment: 2,4-D was developed during World War II at British Rothamsted Experimental Station by Judah Hirsch Quastel and sold commercially in 1946. 2,4-D was developed by a British team during World War II and first saw widespread production and use in the late 1940s.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094123 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7504253 |
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Target ID: CHEMBL339 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15203183 |
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Target ID: CHEMBL1947 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27410513 |
463.0 µM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Immunodetection of hepatic peroxisomal PMP70 as an indicator of peroxisomal proliferation in the mummichog, Fundulus heteroclitus. | 2000 Jul-Dec |
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Effects of spraying the herbicides 2,4-D and 2,4,5-T on a population of the tortoise Testudo hermanni in southern Greece. | 2001 |
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Galantamine for Alzheimer's disease. | 2001 |
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Propagation of Coriandrum sativum L. through somatic embryogenesis. | 2001 Apr |
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Intracerebral administration of 2,4-diclorophenoxyacetic acid induces behavioral and neurochemical alterations in the rat brain. | 2001 Apr |
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Characterization of (R/S)-mecoprop [2-(2-methyl-4-chlorophenoxy) propionic acid]-degrading Alcaligenes sp.CS1 and Ralstonia sp. CS2 isolated from agricultural soils. | 2001 Apr |
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Antigenic variation of gonococcal pilin expression in vivo: analysis of the strain FA1090 pilin repertoire and identification of the pilS gene copies recombining with pilE during experimental human infection. | 2001 Apr |
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Leaching of 2,4-D from a soil in the presence of beta-cyclodextrin: laboratory columns experiments. | 2001 Aug |
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Molecular characterization of a deletion/duplication rearrangement in tfd genes from Ralstonia eutropha JMP134(pJP4) that improves growth on 3-chlorobenzoic acid but abolishes growth on 2,4-dichlorophenoxyacetic acid. | 2001 Aug |
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Neuregulins increase alpha7 nicotinic acetylcholine receptors and enhance excitatory synaptic transmission in GABAergic interneurons of the hippocampus. | 2001 Aug 1 |
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Uptake of endocytic markers by rice cells: variations related to the growth phase. | 2001 Feb |
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Quantitative and qualitative precision improvements by effective mobility-scale data transformation in capillary electrophoresis analysis. | 2001 Jan |
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Mortality in chemical workers potentially exposed to 2,4-dichlorophenoxyacetic acid (2,4-D) 1945-94: an update. | 2001 Jan |
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Regulation of DNA binding and trans-activation by a xenobiotic stress-activated plant transcription factor. | 2001 Jan 5 |
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Genotoxic effect of 2,4-dichlorophenoxy acetic acid and its metabolite 2,4-dichlorophenol in mouse. | 2001 Jul 25 |
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Unique renal tubule changes induced in rats and mice by the peroxisome proliferators 2,4-dichlorophenoxyacetic acid (2,4-D) and WY-14643. | 2001 Jul-Aug |
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Development of sampling and analytical methods for concerted determination of commonly used chloroacetanilide, chlorotriazine, and 2,4-D herbicides in hand-wash, dermal-patch, and air samples. | 2001 Jun |
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In vitro plantlet regeneration in Panax sikkimensis. | 2001 Mar |
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Growth and production of camptothecin by cell suspension cultures of Nothapodytes foetida. | 2001 Mar |
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Continuing research into Gulf War illness. | 2001 May 4 |
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Laboratory degradation studies of bentazone, dichlorprop, MCPA, and propiconazole in Norwegian soils. | 2001 May-Jun |
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Atrazine, isoproturon, mecoprop, 2,4-D, and bentazone adsorption onto iron oxides. | 2001 May-Jun |
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Toxic effects of the herbicide 2,4-dichlorophenoxyacetic acid on lymphoid organs of the rat. | 2001 May-Jun |
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Determination of bentazone, dichlorprop, and MCPA in different soils by sodium hydroxide extraction in combination with solid-phase preconcentration. | 2001 Sep |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9374285
Neonate rats were treated with 2,4-dichlorophenoxyacetic acid (2,4-D) from the 7th or 12th until the 17th or 25th postnatal day. Two drug dosages were used: 70 and 100 mg/kg body weight of 2,4-D. At the 17th day of age, no changes were observed in body weight, protein and DNA content. However, 25-day-old treated pups showed diminutions in body and brain weight, protein and DNA levels, depending on doses and period of treatment.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27432240
Different doses of 2,4-D (10 nM, 100 nM, 1 uM, 10 uM, 100 uM, and 200 uM) were applied to human spermatozoa prepared from normal fresh semen samples. The results indicated that 2,4-D did not affect the viability, capacitation, or spontaneous acrosome reactions of human spermatozoa, but it dose-dependently inhibited the total motility, progressive motility, ability to penetrate viscous medium, and progesterone-induced capacitation and acrosome reaction rates.
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ACTIVE MOIETY
SUBSTANCE RECORD