1928-38-7

Usage

Uses

Used in Agricultural Industry:
Methyl (2,4-dichlorophenoxy)acetate is used as a pesticide and herbicide for controlling a wide range of broadleaf weeds in various crops. Its application reason is its ability to mimic plant growth hormones, causing uncontrolled growth and eventually leading to the death of the targeted weeds.
However, due to the potential health and environmental concerns associated with 2,4-DMA, its use is heavily regulated in many countries to minimize its potential negative impacts. This includes restrictions on application methods, buffer zones, and maximum application rates to protect non-target plants, wildlife, and human health.

InChI:InChI=1/C9H8Cl2O3/c1-6(12)13-5-14-9-3-2-7(10)4-8(9)11/h2-4H,5H2,1H3

Upstream product

• 67-56-1 methanol 
• 94-75-7 2,4-Dichlorophenoxyacetic acid 
• 2008-39-1 2,4-dichlorophenoxyacetic acid dimethylamine 
• 112-62-9 Methyl oleate 
• 6212-47-1 n-propyl phenoxyacetate 
• 2065-23-8 methyl 2-phenoxyacetate 
• 108-95-2 phenol 
• 96-32-2 bromoacetic acid methyl ester 
• 120-83-2 2,4-dichlorophenol 
• 96-34-4 methyl chloroacetate 
• 74-88-4 methyl iodide 

Downstream Products

• 87157-40-2 N-[(2,4-dichloro-phenoxy)-acetyl]-N-methyl-D-glucamine 
• 87651-68-1 Bromo-(2,4-dichloro-phenoxy)-acetic acid methyl ester 
• 28236-62-6 2,4-dichlorophenoxyacetylhydrazine 
• 24573-72-6 Bis-(2,4-dichlor-phenoxy)-essigsaeuremethylester 
• 87651-72-7 (2,4-Dichloro-phenoxy)-thiocyanato-acetic acid methyl ester 
• 87651-76-1 (2,4-Dichloro-phenoxy)-isothiocyanato-acetic acid methyl ester 
• 87651-83-0 (2,4-Dichloro-phenoxy)-phenoxy-acetic acid methyl ester 
• 87651-84-1 (4-Chloro-phenoxy)-(2,4-dichloro-phenoxy)-acetic acid methyl ester 
• 87651-79-4 Azido-(2,4-dichloro-phenoxy)-acetic acid methyl ester 
• 94-75-7 2,4-Dichlorophenoxyacetic acid 
• 50848-29-8 5-(2,4-dichloro-phenoxymethyl)-3H-[1,3,4]oxadiazole-2-thione 

Relevant academic research and scientific papers

Glove permeation tests using novel microchemical techniques for 2,4- dichlorophenoxyacetic acid (2,4-D) derivatives

The aim was to assess the permeation of different herbicide emulsion concentrate formulations of 2,4-dichlorophenoxyacetic acid (2,4-D) as 60.8 and 83.5% butoxyethy] ester (BEE) and 46.8% dimethyl amine salt (DMAS) through four types of glove materials (l

Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite

In this work, the green esterification of carboxylic acids promoted by tert-butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.

Carboxylic Acid Reductase Can Catalyze Ester Synthesis in Aqueous Environments

Most of the well-known enzymes catalyzing esterification require the minimization of water or activated substrates for activity. This work reports a new reaction catalyzed by carboxylic acid reductase (CAR), an enzyme known to transform a broad spectrum of carboxylic acids into aldehydes, with the use of ATP, Mg2+, and NADPH as co-substrates. When NADPH was replaced by a nucleophilic alcohol, CAR from Mycobacterium marinum can catalyze esterification under aqueous conditions at room temperature. Addition of imidazole, especially at pH 10.0, significantly enhanced ester production. In comparison to other esterification enzymes such as acyltransferase and lipase, CAR gave higher esterification yields in direct esterification under aqueous conditions. The scalability of CAR catalyzed esterification was demonstrated for the synthesis of cinoxate, an active ingredient in sunscreen. The CAR esterification offers a new method for green esterification under high water content conditions.

Novel lipophilic analogues from 2,4-D and Propanil herbicides: Biological activity and kinetic studies

This work describes the synthesis of new lipophilic amides and esters analogues of classical organochlorides herbicides by incorporation of long-chains from fatty acids and derivatives. The new fatty esters and amides were synthesized in 96–99percent and 80–89percent yields, respectively. In general, all compounds tested showed superior in vitro activity than commercial herbicides against growth L. sativa and A. cepa, in ranges 86–100percent of germinative inhibition. The target compounds showed, significantly more susceptible towards acid hydrolysis than 2,4-dichlorophenoxyacetic acid (2,4-D). The kinetic and NMR studies showed that the incorporation of lipophilic chains resulted in a decrease in half-life time of new herbicides compounds (1.5 h) than 2,4-D (3 h). These findings suggest the synthesis of new lipophilic herbicides as potential alternative to traditional formulations, by incorporation of long fatty alkyl chains in the molecular structure of 2,4-D, resulting in superior in vitro herbicidal activity, best degradation behavior and more hydrophobic derivatives.

ACLY INHIBITORS AND USES THEREOF

The present invention provides compounds useful as inhibitors of ATP citrate lyase (ACLY), compositions thereof, and methods of using the same.

Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors

A series of aryloxyacetic acid derivatives were designed and synthesized as 4-hydoxyphenylpyruvate dioxygenase (HPPD) inhibitors. Preliminary bioassay results reveal that these derivatives are promising Arabidopsis thaliana HPPD (AtHPPD) inhibitors, in particular compounds I12 (Ki = 0.011 μM) and I23 (Ki = 0.012 μM), which exhibit similar activities to that of mesotrione, a commercial HPPD herbicide (Ki = 0.013 μM). Furthermore, the newly synthesized compounds show significant greenhouse herbicidal activities against tested weeds at dosages of 150 g ai/ha. In particular, II4 exhibited high herbicidal activity for pre-emergence treatment that was slightly better than that of mesotrione. In addition, compound II4 was safe for weed control in maize fields at a rate of 150 g ai/ha, and was identified as the most potent candidate for a novel HPPD inhibitor herbicide. The compounds described herein may provide useful guidance for the design of new HPPD inhibiting herbicides and their modification.

Synthesis method of 2, 4-dichlorophenoxyacetic acid compound

The invention relates to a synthesis method of a 2, 4-dichlorophenoxyacetic acid compound, and relates to the technical field of organic synthesis. The synthesis method of the 2, 4-dichlorophenoxyacetic acid compound is to solve the problems of many by-products existing in synthesis method of the 2, 4-dichlorophenoxyacetic acid compound in prior art, low conversion of phenol, incomplete conversion, environmental pollution resulted, the use of a large number of solvents, production of a large amount of wastewater, high cost, complex technology, high environmental risk, and being not conducive to industrial production. According to the synthesis method of the 2, 4-dichlorophenoxyacetic acid compound, in the synergistic action of anhydrous carbonate weak base and a catalyst, performing condensation of 2, 4-dichlorophenol with halogen acetate, and 2, 4-dichlorophenoxyacetic acid is obtained directly by hydrolysis and acidification. The process of the synthesis method of the 2, 4-dichlorophenoxyacetic acid compound is accomplished by condensation, hydrolysis and acid hydrolysis in one pot without any solvent and using anhydrous carbonate weak base to react with 2, 4-dichlorophenol can effectively inhibit the hydrolysis of chloroacetate, improve the condensation conversion, reduce the content of free phenol, keep a yield over 97% an active ingredient more than 98%, and free phenol content in 50-100 ppm.

Synthesis method of substituted phenoxyacetate compound

The invention discloses a synthesis method of a substituted phenoxyacetate compound, relates to a synthesis method of a compound and aims to solve the problems that during current preparation of the substituted phenoxyacetate compound by a condensation method, a large amount of organic agent is consumed, substituted phenol is unlikely to react completely, the content of free phenol in three wastesis high and a very high environmental risk exists. According to the synthesis method, after the substituted phenol is mixed with haloacetate, a condensation reaction is performed in a potassium fluoride system condensing agent under the synergistic catalysis of a phase transfer catalyst and a halogenated hydrocarbon activator to obtain a substituted phenoxyacetic acid compound. The synthesis method is applied to the field of compound synthesis.

Design and Synthesis of Novel 4-Hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one Derivatives for Use as Herbicides and Evaluation of Their Mode of Action

In order to develop a novel herbicide containing the β-triketone motif, a series of 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one derivatives were designed and synthesized. The bioassay results showed that compound II15 had good pre-emergent herbicidal activity even at a dosage of 187.5 g ha-1. Moreover, compound II15 showed a broader spectrum of weed control when compared with a commercial herbicide 2,4-dichlorophenoxyacetic acid (2,4-D), and displayed good crop safety to Triticum aestivum L. and Zea mays Linn. when applied at 375 g ha-1 under pre-emergence conditions, which indicated its great potential as a herbicide. More importantly, studying the molecular mode of action of compound II15 revealed that the novel triketone structure is a proherbicide of its corresponding phenoxyacetic acid auxin herbicide, which has a herbicidal mechanism similar to that of 2,4-D. The present work indicates that the 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one motif may be a potential lead structure for further development of novel auxin-type herbicides.

Synthesis and computer-aided SAR studies for derivatives of phenoxyalkyl-1,3,5-triazine as the new potent ligands for serotonin receptors 5-HT6

This research has provided the most active 5-HT6R agents among 1,3,5-triazine derivatives investigated to date and has also identified the world's first selenium-containing 5-HT6R ligands. The studies are focused on design, synthesis, biological evaluation and docking-supported SAR analysis for novel 5-HT6R agents as derivatives of lead structure 4-(4-methylpiperazin-1-yl)-6-(phenoxymethyl)-1,3,5-triazin-2-amine (7). The lead modifications included an introduction of: (i) various small substituents at benzene ring, (ii) a branched ether linker or (iii) the ether oxygen replacement with other chalcogen (S, Se) or sulfonyl moiety. Hence, a series of new compounds (7–24) was synthesized and examined on their affinities for 5-HT6R and selectivity, in respect to the 5-HT1AR, 5-HT2AR, 5-HT7R and dopamine D2 receptor, in the radioligand binding assays. For representative most active compounds functional bioassays and toxicity profile in vitro and antidepressant-like activity in vivo were examined. The 2-isopropyl-5-methylphenyl derivative (10) was found as the most active triazine 5-HT6R antagonist (Ki = 11 nM). SAR analysis indicated, that an exchange of oxygen to selenium (7 vs. 22), and especially, to sulfur (7 vs. 19) was beneficial to increase both affinity and antagonistic action for 5-HT6R. Surprisingly, an introduction of SO2 caused a drastic decrease of the 5-HT6R affinity, which was explained at a molecular level based on docking studies. All in vivo tested compounds (10, 18 and 21) did not show any risk of toxicity in the safety studies in vitro.