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=CC=C(Cl)C=C1Cl.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.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Evaluation of plant growth promoting and colonization ability of endophytic diazotrophs from deep water rice. | 2001-10-04 |
|
| Kinetic modeling of bioavailability for sorbed-phase 2,4-dichlorophenoxyacetic acid. | 2001-10-02 |
|
| In vivo and in vitro binding of 2,4-dichlorophenoxyacetic acid to a rat liver mitochondrial protein. | 2001-09-28 |
|
| Unique renal tubule changes induced in rats and mice by the peroxisome proliferators 2,4-dichlorophenoxyacetic acid (2,4-D) and WY-14643. | 2001-09-19 |
|
| Combined effects of an oxidative enzyme and dissolved humic substances on 13C-labelled 2,4-D herbicide as revealed by high-resolution 13C NMR spectroscopy. | 2001-09-11 |
|
| Development of a flow injection capillary chemiluminescent ELISA using an imprinted polymer instead of the antibody. | 2001-09-01 |
|
| Determination of bentazone, dichlorprop, and MCPA in different soils by sodium hydroxide extraction in combination with solid-phase preconcentration. | 2001-09 |
|
| Three Tnt1 subfamilies show different stress-associated patterns of expression in tobacco. Consequences for retrotransposon control and evolution in plants. | 2001-09 |
|
| Eucalyptus camaldulensis: volatiles from immature flowers and high production of 1,8-cineole and beta-pinene by in vitro cultures. | 2001-09 |
|
| Analysis of acidic pesticides using in situ derivatization with alkylchloroformate and solid-phase microextraction (SPME) for GC-MS. | 2001-09 |
|
| Amyotrophic lateral sclerosis and occupational exposure to 2,4-dichlorophenoxyacetic acid. | 2001-09 |
|
| Induction of sister chromatid exchanges by 2,4-dichlorophenoxyacetic acid in somatic and germ cells of mice exposed in vivo. | 2001-09 |
|
| Cytogenetic monitoring of croatian population occupationally exposed to a complex mixture of pesticides. | 2001-08-28 |
|
| The effect of exposure to a commercial 2,4-D formulation during gestation on the immune response in CD-1 mice. | 2001-08-13 |
|
| Neuregulins increase alpha7 nicotinic acetylcholine receptors and enhance excitatory synaptic transmission in GABAergic interneurons of the hippocampus. | 2001-08-01 |
|
| Modeling the quantum yields of herbicide 2,4-D decay in UV/H2O2 process. | 2001-08 |
|
| Simultaneous recovery of copper and degradation of 2,4-dichlorophenoxyacetic acid in aqueous systems by a combination of electrolytic and photolytic processes. | 2001-08 |
|
| Leaching of 2,4-D from a soil in the presence of beta-cyclodextrin: laboratory columns experiments. | 2001-08 |
|
| 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. | 2001-08 |
|
| Dioxin and dioxin-like PCB impurities in some Japanese agrochemical formulations. | 2001-08 |
|
| Genotoxic effect of 2,4-dichlorophenoxy acetic acid and its metabolite 2,4-dichlorophenol in mouse. | 2001-07-25 |
|
| Molecular recognition in imprinted polymers: thermodynamic investigation of analyte binding using microcalorimetry. | 2001-07-20 |
|
| Immunodetection of hepatic peroxisomal PMP70 as an indicator of peroxisomal proliferation in the mummichog, Fundulus heteroclitus. | 2001-07-20 |
|
| Interactions of atrazine and 2,4-D with human serum albumin studied by gel and capillary electrophoresis, and FTIR spectroscopy. | 2001-07-09 |
|
| The development of a new method to estimate total daily dose of pesticides in professional turf applicators following multiple and varied exposures in occupational settings. | 2001-07 |
|
| Determination of pesticides in drinking water by micellar electrokinetic capillary chromatography. | 2001-07 |
|
| Separation of chlorophenoxyacetic acids and chlorophenols by using capillary zone electrophoresis. | 2001-07 |
|
| Sorption of herbicides in relation to soil variability and landscape position. | 2001-07 |
|
| Selection of hybrids and edible citrus species with a high content in the diosmin functional compound. Modulating effect of plant growth regulators on contents. | 2001-07 |
|
| Prostate cancer detection in veterans with a history of Agent Orange exposure. | 2001-07 |
|
| Serum dioxin and hepatic abnormalities in veterans of Operation Ranch Hand. | 2001-07 |
|
| Modulation of cell proliferation by heterotrimeric G protein in Arabidopsis. | 2001-06-15 |
|
| Laboratory degradation studies of bentazone, dichlorprop, MCPA, and propiconazole in Norwegian soils. | 2001-06-13 |
|
| Atrazine, isoproturon, mecoprop, 2,4-D, and bentazone adsorption onto iron oxides. | 2001-06-13 |
|
| Adsorption of pesticides onto quartz, calcite, kaolinite, and alpha-alumina. | 2001-06-13 |
|
| 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. | 2001-06 |
|
| Biological activity of alpha-thujaplicin, the minor component of Thujopsis dolabrata SIEB. et ZUCC. var. hondai MAKINO. | 2001-06 |
|
| Uniformly (14)C-ring-labeled 2,4-dichlorophenoxyacetic acid: a metabolism study in bluegill sunfish, Lepomis macrochirus. | 2001-06 |
|
| Mineralization of 2,4-D, mecoprop, isoproturon and terbuthylazine in a chalk aquifer. | 2001-06 |
|
| [Effect of rye chromosomes on features of androgenesis in wheat-rye substituted lines of Triticum aestivum L. sort Saratovskaya 29/Secale cerale L. sort Onokhoiskaia and Triticale]. | 2001-05 |
|
| Biomarker correlations of urinary 2,4-D levels in foresters: genomic instability and endocrine disruption. | 2001-05 |
|
| Propagation of Coriandrum sativum L. through somatic embryogenesis. | 2001-04 |
|
| Partial characterization of genes whose transcripts accumulate preferentially in cell clusters at the earliest stage of carrot somatic embryogenesis. | 2001-04 |
|
| Intracerebral administration of 2,4-diclorophenoxyacetic acid induces behavioral and neurochemical alterations in the rat brain. | 2001-04 |
|
| Effects of temperature and concentration of the accelerators ethoxylated alcohols, diethyl suberate and tributyl phosphate on the mobility of [14C]2,4-dichlorophenoxy butyric acid in plant cuticles. | 2001-01 |
|
| Physiological and genetic characteristics of two bacterial strains utilizing phenoxypropionate and phenoxyacetate herbicides. | 2001 |
|
| Effect of the herbicide 4-CPA on human erythrocyte antioxidant enzymes in vitro. | 2001 |
|
| Morphohistobiochemical characteristics of embryogenic and nonembryogenic callus cultures of sweet potato (Ipomoea batatas L.). | 2001 |
|
| Spatial expression of DNA topoisomerase I genes during cell proliferation in Daucus carota. | 2001 |
|
| In vitro propagation and rhizome formation in Curcuma longa Linn. | 2001 |
Sample Use Guides
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
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
Mon Mar 31 22:32:37 GMT 2025
by
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on
Mon Mar 31 22:32:37 GMT 2025
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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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