Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C8H6Cl2O3 |
| Molecular Weight | 221.037 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)COC1=CC=C(Cl)C=C1Cl
InChI
InChIKey=OVSKIKFHRZPJSS-UHFFFAOYSA-N
InChI=1S/C8H6Cl2O3/c9-5-1-2-7(6(10)3-5)13-4-8(11)12/h1-3H,4H2,(H,11,12)
| 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 |
|---|---|---|
| Immunodetection of hepatic peroxisomal PMP70 as an indicator of peroxisomal proliferation in the mummichog, Fundulus heteroclitus. | 2000 Jul-Dec |
|
| Physiological and genetic characteristics of two bacterial strains utilizing phenoxypropionate and phenoxyacetate herbicides. | 2001 |
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| Effect of the herbicide 4-CPA on human erythrocyte antioxidant enzymes in vitro. | 2001 |
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| 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 |
|
| Propagation of Coriandrum sativum L. through somatic embryogenesis. | 2001 Apr |
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| Partial characterization of genes whose transcripts accumulate preferentially in cell clusters at the earliest stage of carrot somatic embryogenesis. | 2001 Apr |
|
| Intracerebral administration of 2,4-diclorophenoxyacetic acid induces behavioral and neurochemical alterations in the rat brain. | 2001 Apr |
|
| Modeling the quantum yields of herbicide 2,4-D decay in UV/H2O2 process. | 2001 Aug |
|
| Simultaneous recovery of copper and degradation of 2,4-dichlorophenoxyacetic acid in aqueous systems by a combination of electrolytic and photolytic processes. | 2001 Aug |
|
| Leaching of 2,4-D from a soil in the presence of beta-cyclodextrin: laboratory columns experiments. | 2001 Aug |
|
| 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 |
|
| Dioxin and dioxin-like PCB impurities in some Japanese agrochemical formulations. | 2001 Aug |
|
| Neuregulins increase alpha7 nicotinic acetylcholine receptors and enhance excitatory synaptic transmission in GABAergic interneurons of the hippocampus. | 2001 Aug 1 |
|
| The effect of exposure to a commercial 2,4-D formulation during gestation on the immune response in CD-1 mice. | 2001 Aug 13 |
|
| Cytogenetic monitoring of croatian population occupationally exposed to a complex mixture of pesticides. | 2001 Aug 28 |
|
| 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 Jan |
|
| 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 Jan-Feb |
|
| 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 Jul |
|
| Determination of pesticides in drinking water by micellar electrokinetic capillary chromatography. | 2001 Jul |
|
| Separation of chlorophenoxyacetic acids and chlorophenols by using capillary zone electrophoresis. | 2001 Jul |
|
| Sorption of herbicides in relation to soil variability and landscape position. | 2001 Jul |
|
| 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 |
|
| Prostate cancer detection in veterans with a history of Agent Orange exposure. | 2001 Jul |
|
| Serum dioxin and hepatic abnormalities in veterans of Operation Ranch Hand. | 2001 Jul |
|
| Molecular recognition in imprinted polymers: thermodynamic investigation of analyte binding using microcalorimetry. | 2001 Jul 20 |
|
| Genotoxic effect of 2,4-dichlorophenoxy acetic acid and its metabolite 2,4-dichlorophenol in mouse. | 2001 Jul 25 |
|
| Interactions of atrazine and 2,4-D with human serum albumin studied by gel and capillary electrophoresis, and FTIR spectroscopy. | 2001 Jul 9 |
|
| 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 |
|
| 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 |
|
| Biological activity of alpha-thujaplicin, the minor component of Thujopsis dolabrata SIEB. et ZUCC. var. hondai MAKINO. | 2001 Jun |
|
| Uniformly (14)C-ring-labeled 2,4-dichlorophenoxyacetic acid: a metabolism study in bluegill sunfish, Lepomis macrochirus. | 2001 Jun |
|
| Mineralization of 2,4-D, mecoprop, isoproturon and terbuthylazine in a chalk aquifer. | 2001 Jun |
|
| Modulation of cell proliferation by heterotrimeric G protein in Arabidopsis. | 2001 Jun 15 |
|
| [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 May |
|
| Biomarker correlations of urinary 2,4-D levels in foresters: genomic instability and endocrine disruption. | 2001 May |
|
| Laboratory degradation studies of bentazone, dichlorprop, MCPA, and propiconazole in Norwegian soils. | 2001 May-Jun |
|
| Atrazine, isoproturon, mecoprop, 2,4-D, and bentazone adsorption onto iron oxides. | 2001 May-Jun |
|
| Adsorption of pesticides onto quartz, calcite, kaolinite, and alpha-alumina. | 2001 May-Jun |
|
| Evaluation of plant growth promoting and colonization ability of endophytic diazotrophs from deep water rice. | 2001 Oct 4 |
|
| Determination of bentazone, dichlorprop, and MCPA in different soils by sodium hydroxide extraction in combination with solid-phase preconcentration. | 2001 Sep |
|
| Three Tnt1 subfamilies show different stress-associated patterns of expression in tobacco. Consequences for retrotransposon control and evolution in plants. | 2001 Sep |
|
| Eucalyptus camaldulensis: volatiles from immature flowers and high production of 1,8-cineole and beta-pinene by in vitro cultures. | 2001 Sep |
|
| Analysis of acidic pesticides using in situ derivatization with alkylchloroformate and solid-phase microextraction (SPME) for GC-MS. | 2001 Sep |
|
| Amyotrophic lateral sclerosis and occupational exposure to 2,4-dichlorophenoxyacetic acid. | 2001 Sep |
|
| Induction of sister chromatid exchanges by 2,4-dichlorophenoxyacetic acid in somatic and germ cells of mice exposed in vivo. | 2001 Sep |
|
| Development of a flow injection capillary chemiluminescent ELISA using an imprinted polymer instead of the antibody. | 2001 Sep 1 |
|
| In vivo and in vitro binding of 2,4-dichlorophenoxyacetic acid to a rat liver mitochondrial protein. | 2001 Sep 28 |
|
| Kinetic modeling of bioavailability for sorbed-phase 2,4-dichlorophenoxyacetic acid. | 2001 Sep-Oct |
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
Fri Dec 15 18:20:13 GMT 2023
by
admin
on
Fri Dec 15 18:20:13 GMT 2023
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| Record UNII |
2577AQ9262
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| Record Status |
Validated (UNII)
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| Record Version |
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EPA PESTICIDE CODE |
30001
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202-361-1
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202
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m4063
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19351
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2,4-DICHLOROPHENOXYACETIC ACID
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94-75-7
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1486
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DTXSID0020442
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28854
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2925
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2,4-D
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2577AQ9262
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| Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
