Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H44N2.C8H6Cl2O3 |
Molecular Weight | 545.625 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)COC1=C(Cl)C=C(Cl)C=C1.CCCCCCCC\C=C/CCCCCCCCNCCCN
InChI
InChIKey=OOJIITFNNWRJKA-KVVVOXFISA-N
InChI=1S/C21H44N2.C8H6Cl2O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20-23-21-18-19-22;9-5-1-2-7(6(10)3-5)13-4-8(11)12/h9-10,23H,2-8,11-22H2,1H3;1-3H,4H2,(H,11,12)/b10-9-;
Molecular Formula | C21H44N2 |
Molecular Weight | 324.5875 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
Molecular Formula | C8H6Cl2O3 |
Molecular Weight | 221.037 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
|||
Target ID: CHEMBL339 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15203183 |
|||
Target ID: CHEMBL1947 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27410513 |
463.0 µM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
2,4-dichlorophenoxyacetate/alpha-ketoglutarate dioxygenases from Burkholderia cepacia 2a and Ralstonia eutropha JMP134. | 2001 |
|
Intracerebral administration of 2,4-diclorophenoxyacetic acid induces behavioral and neurochemical alterations in the rat brain. | 2001 Apr |
|
Different pathways are involved in phosphate and iron stress-induced alterations of root epidermal cell development. | 2001 Apr |
|
Combined effects of food concentration and the herbicide 2,4-dichlorophenoxyacetic acid on the population dynamics of Brachionus patulus (Rotifera). | 2001 Apr |
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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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The effect of exposure to a commercial 2,4-D formulation during gestation on the immune response in CD-1 mice. | 2001 Aug 13 |
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Cytogenetic monitoring of croatian population occupationally exposed to a complex mixture of pesticides. | 2001 Aug 28 |
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Diffuse geographic distribution of herbicides in northern prairie wetlands. | 2001 Feb |
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Transport of [3H]MPP+ in an immortalized rat brain microvessel endothelial cell line (RBE 4). | 2001 Jan |
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Induction of apoptosis in human lymphocytes by the herbicide 2,4-dichlorophenoxyacetic acid. | 2001 Jan |
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Primary structure and expression of a 24-kD vacuolar protein (VP24) precursor in anthocyanin-producing cells of sweet potato in suspension culture. | 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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Simultaneous determination of 2,4-D and MCPA in canine plasma and urine by HPLC with fluorescence detection using 9-anthryldiazomethane (ADAM). | 2001 Jan-Feb |
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Selection of hybrids and edible citrus species with a high content in the diosmin functional compound. Modulating effect of plant growth regulators on contents. | 2001 Jul |
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Mineralization of 2,4-D, mecoprop, isoproturon and terbuthylazine in a chalk aquifer. | 2001 Jun |
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Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens. | 2001 Mar |
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Biomarker correlations of urinary 2,4-D levels in foresters: genomic instability and endocrine disruption. | 2001 May |
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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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Development of a flow injection capillary chemiluminescent ELISA using an imprinted polymer instead of the antibody. | 2001 Sep 1 |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 09:11:01 GMT 2023
by
admin
on
Sat Dec 16 09:11:01 GMT 2023
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Record UNII |
6SXX02U73Y
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Record Status |
Validated (UNII)
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Record Version |
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6435899
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7286-81-9
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6SXX02U73Y
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2212-61-5
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DTXSID6040327
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2212-59-1
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