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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
Structure of 2,4-D-TRIS(2-HYDROXYPROPYL)AMMONIUM

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)

HIDE SMILES / InChI
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

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

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Immunodetection of hepatic peroxisomal PMP70 as an indicator of peroxisomal proliferation in the mummichog, Fundulus heteroclitus.
2000 Jul-Dec
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
Galantamine for Alzheimer's disease.
2001
Propagation of Coriandrum sativum L. through somatic embryogenesis.
2001 Apr
Intracerebral administration of 2,4-diclorophenoxyacetic acid induces behavioral and neurochemical alterations in the rat brain.
2001 Apr
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
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
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
Neuregulins increase alpha7 nicotinic acetylcholine receptors and enhance excitatory synaptic transmission in GABAergic interneurons of the hippocampus.
2001 Aug 1
Uptake of endocytic markers by rice cells: variations related to the growth phase.
2001 Feb
Quantitative and qualitative precision improvements by effective mobility-scale data transformation in capillary electrophoresis analysis.
2001 Jan
Mortality in chemical workers potentially exposed to 2,4-dichlorophenoxyacetic acid (2,4-D) 1945-94: an update.
2001 Jan
Regulation of DNA binding and trans-activation by a xenobiotic stress-activated plant transcription factor.
2001 Jan 5
Genotoxic effect of 2,4-dichlorophenoxy acetic acid and its metabolite 2,4-dichlorophenol in mouse.
2001 Jul 25
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
In vitro plantlet regeneration in Panax sikkimensis.
2001 Mar
Growth and production of camptothecin by cell suspension cultures of Nothapodytes foetida.
2001 Mar
Continuing research into Gulf War illness.
2001 May 4
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
Toxic effects of the herbicide 2,4-dichlorophenoxyacetic acid on lymphoid organs of the rat.
2001 May-Jun
Determination of bentazone, dichlorprop, and MCPA in different soils by sodium hydroxide extraction in combination with solid-phase preconcentration.
2001 Sep
Patents

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.
Name Type Language
2,4-D-TRIS(2-HYDROXYPROPYL)AMMONIUM
ISO  
Common Name English
2,4-D, TRIISOPROPANOLAMINE SALT
Common Name English
ACETIC ACID, (2,4-DICHLOROPHENOXY)-, COMPD. WITH 1,1',1''-NITRILOTRI-2-PROPANOL (1:1)
Systematic Name English
TRIS(2-HYDROXYPROPYL)AMINE/2,4-DICHLOROPHENOXYACETIC ACID,(1:1)
Common Name English
2,4-D TRIISOPROPANOLAMINE
Systematic Name English
2,4-D-TRIS(2-HYDROXYPROPYL)AMMONIUM [ISO]
Common Name English
2,4-D TRIISOPROPANOLAMMONIUM SALT
Systematic Name English
EPA PESTICIDE CHEMICAL CODE 030035
Code English
ACETIC ACID, 2-(2,4-DICHLOROPHENOXY)-, COMPD. WITH 1,1',1''-NITRILOTRIS(2-PROPANOL) (1:1)
Systematic Name English
TRIISOPROPANOLAMINE 2,4-DICHLOROPHENOXYACETATE
Common Name English
CURTAIL
Brand Name English
2-PROPANOL, 1,1',1''-NITRILOTRI-, (2,4-DICHLOROPHENOXY)ACETATE (SALT)
Systematic Name English
2,4-DICHLOROPHENOXYACETIC ACID TRIS(2-HYDROXYPROPYL)AMINE
Systematic Name English
J388.293D
Code English
(2,4-DICHLOROPHENOXY)ACETIC ACID - 1,1',1''-NITRILOTRI(2-PROPANOL) (1:1)
Systematic Name English
Code System Code Type Description
CAS
18584-79-7
Created by admin on Sat Dec 16 10:42:35 GMT 2023 , Edited by admin on Sat Dec 16 10:42:35 GMT 2023
PRIMARY
CAS
29450-66-6
Created by admin on Sat Dec 16 10:42:35 GMT 2023 , Edited by admin on Sat Dec 16 10:42:35 GMT 2023
SUPERSEDED
CAS
32341-80-3
Created by admin on Sat Dec 16 10:42:35 GMT 2023 , Edited by admin on Sat Dec 16 10:42:35 GMT 2023
SUPERSEDED
PUBCHEM
62724
Created by admin on Sat Dec 16 10:42:35 GMT 2023 , Edited by admin on Sat Dec 16 10:42:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID8034243
Created by admin on Sat Dec 16 10:42:35 GMT 2023 , Edited by admin on Sat Dec 16 10:42:35 GMT 2023
PRIMARY
FDA UNII
0AW5Y1G7RO
Created by admin on Sat Dec 16 10:42:35 GMT 2023 , Edited by admin on Sat Dec 16 10:42:35 GMT 2023
PRIMARY