2,4-Dichlorophenoxyacetic acid
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| Category | Agricultural |
| Catalog number | BBF-05905 |
| CAS | 94-75-7 |
| Molecular Weight | 221.03 |
| Molecular Formula | C8H6Cl2O3 |
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Description
2,4-Dichlorophenoxyacetic acid is an auxin found in Guanomyces polythrix and Phoma herbarum, which is used as an herbicide used to control broadleaf weeds.
Specification
| Synonyms | (2,4-Dichlorophenoxy)acetic acid |
| IUPAC Name | 2-(2,4-dichlorophenoxy)acetic acid |
| Canonical SMILES | C1=CC(=C(C=C1Cl)Cl)OCC(=O)O |
| InChI | InChI=1S/C8H6Cl2O3/c9-5-1-2-7(6(10)3-5)13-4-8(11)12/h1-3H,4H2,(H,11,12) |
| InChI Key | OVSKIKFHRZPJSS-UHFFFAOYSA-N |
Properties
| Application | Herbicide |
| Melting Point | 140.5°C |
| LogP | 2.81 |
Toxicity
| Carcinogenicity | 2B, possibly carcinogenic to humans. |
| Lethal Dose | 80-800 mg/kg (Oral). |
| Mechanism Of Toxicity | 2,4-Dichlorophenoxyacetic acid is a strong oxidant and is known to cause lipid peroxidation and the generation of free radicals that can modify lipids and proteins. It is also known to inhibit glutathione S transferase which leads to a depletion of ATP, NADPH and glutathione. These actions can cause cell toxicity and apopotosis among metabolically active cells. Some of the endocrine effects of 2,4-D may be mediated by the 2,4-D mediated displacement of sex hormones from the sex hormone binding globulin or the 2,4-D mediated blocking or OAT6 transport proteins that are needed for the transport of functional organic ions and dicarboxylates (including estrone sulfate). |
| Toxicity | LD50: 1400 mg/kg (Dermal, Rabbit); LD50: 469 mg/kg (Oral, Guinea pig); LD50: 639 mg/kg (Oral, Rat); LD50: 138 mg/kg (Oral, Mouse). |
Reference Reading
1. 2,4-Dichlorophenoxyacetic acid (2,4-D) affects DNA integrity and retina structure in zebrafish larvae
Sonia Gaaied, Miguel Oliveira, Angela Barreto, Abdelfattah Zakhama, Mohamed Banni Environ Sci Pollut Res Int. 2022 Dec;29(56):85402-85412. doi: 10.1007/s11356-022-21793-8. Epub 2022 Jul 6.
Monitoring the potential risk of herbicides in non-target organisms is a crucial issue for environmental safety. 2,4-D is an herbicide of high environmental relevance that has been shown to exert toxic effects to soil and aquatic biota. In the present study, we investigated the possible genotoxic and retinal development effects of 2,4-dichlorophenoxyacetic acid (2,4-D) herbicide in early life stages zebrafish (Danio rerio). Genotoxicity was evaluated by measuring DNA damage using the comet assay and also by the mRNA expression of genes implicated in apoptosis and/or DNA repair. Retinal development toxicity was evaluated with histological approach. The results obtained revealed that 2,4-D alters DNA integrity of zebrafish larvae. Moreover, transcriptomic data showed a significant induction of p-53 and casp-3 genes and a significant decrease of lig-4 in larvae exposed to the highest tested concentration of 2,4-D (0.8 mg/L). This suggested that p-53 gene regulates the process of DNA repair and apoptosis with increased levels of 2,4-D. The histopathological analysis revealed that early exposure to 2,4-D damaged the structure of larvae retina. Overall, this study is the first to report the DNA damage, casp-3, lig-4 and p-53 regulation, as well as the ocular developmental toxicity in zebrafish larvae at environmentally relevant concentrations of 2,4-D herbicide.
2. The effect of 2,4-dichlorophenoxyacetic acid on the production of oat ( Avena sativa L.) doubled haploid lines through wide hybridization
Katarzyna Juzoń, Marzena Warchoł, Kinga Dziurka, Ilona Mieczysława Czyczyło-Mysza, Izabela Marcińska, Edyta Skrzypek PeerJ. 2022 Jan 31;10:e12854. doi: 10.7717/peerj.12854. eCollection 2022.
Background: Development of new cultivars is one of the vital options for adapting agriculture to climate change, and the production of doubled haploid (DH) plants can make a significant contribution to accelerating the breeding process. Oat is one of the cereals with particular health benefits, but it unfortunately still remains recalcitrant to haploidization. Our previous studies have clearly demonstrated that post-pollination with hormone treatment is a key step in haploid production through wide hybridization and indicated it as the most effective method for this species. Therefore, we subsequently addressed the problem of the influence of 2,4-dichlorophenoxyacetic acid (2,4-D) concentration on consecutive stages of DH production. Methods: Twenty-nine genotypes were tested, 9,465 florets were pollinated with maize pollen 2 days after emasculation and then treated with 2,4-D at 50 mg/L and 100 mg/L. Results: The applied treatments did not reveal any differences in the number of obtained haploid embryos. However, almost twice as many haploid plants formed on MS medium after applying a higher auxin concentration and 20% more successfully acclimatized. Moreover, 100 mg/L 2,4-D treatment resulted in twice as many DH lines that produced almost three times more seeds compared to 50 mg/L treatment. Nevertheless, the results have confirmed the existence of strong genotypic variation, which may significantly limit the development of an effective and economically feasible method that could be incorporated into breeding programs.
3. Preparation of UiO-66-NH2 and UiO-66-NH2/sponge for adsorption of 2,4-dichlorophenoxyacetic acid in water
Sumei Li, Fan Feng, Sha Chen, Xiaolei Zhang, Yixuan Liang, Saisai Shan Ecotoxicol Environ Saf. 2020 May;194:110440. doi: 10.1016/j.ecoenv.2020.110440. Epub 2020 Mar 10.
MOFs are usually used as efficient adsorbents to remove specific pollutants in water. However, because of their poor water stability relatively small particle size, their application in adsorbing and removing pollutants from water is limited. In this paper, with nitrile rubber sponge as the substrate, UiO-66-NH2/sponge composites were firstly in-situ synthesized and systematically evaluated UiO-66-NH2 as an adsorbent to remove 2,4-dichlorophenoxyacetic acid from water. This composite could not only remain the adsorption capacity for 2,4-dichlorophenoxyacetic acid of UiO-66-NH2, but also was much more convenient for separation after the adsorption compared to UiO-66-NH2. In addition, the mechanism of the adsorption of UiO-66-NH2 for 2,4-dichlorophenoxyacetic acid were discussed in detail. Electrostatic interaction between UiO-66-NH2 and 2,4-dichlorophenoxyacetic acid was the main adsorption mechanism. The adsorption was mainly suitable for Langmuir isotherm models, and its maximum adsorption capacity of 2,4-dichlorophenoxyacetic acid was 72.99 mg g-1.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C8H6Cl2O3
Molecular Weight (Monoisotopic Mass): 219.9694 Da
Molecular Weight (Avergae Mass): 221.037 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C8H6Cl2O3
Molecular Weight (Monoisotopic Mass): 219.9694 Da
Molecular Weight (Avergae Mass): 221.037 Da
LC-MS/MS Spectrum - LC-ESI-ITFT , negative
Experimental Conditions
Instrument Type: LC-ESI-ITFT
Ionization Mode: negative
Ionization Mode: negative
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C8H6Cl2O3
Molecular Weight (Monoisotopic Mass): 219.9694 Da
Molecular Weight (Avergae Mass): 221.037 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C8H6Cl2O3
Molecular Weight (Monoisotopic Mass): 219.9694 Da
Molecular Weight (Avergae Mass): 221.037 Da
Mass Spectrum (Electron Ionization)
1H NMR Spectrum
Experimental Conditions
Solvent: DMSO-d6
Instrument Type: JEOL
Nucleus: 1H
Frequency: 400 MHz
Chemical Shift Reference: TMS
Instrument Type: JEOL
Nucleus: 1H
Frequency: 400 MHz
Chemical Shift Reference: TMS
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Bio Calculators
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