588-20-5

Usage

Uses

Used in Agricultural Industry:
(4-CHLORO-3-METHYL-PHENOXY)-ACETIC ACID is used as a post-emergence broadleaf herbicide for controlling a variety of weeds in agricultural settings. It functions by disrupting the growth of weeds, thereby inhibiting their ability to compete with crops for essential nutrients and resources, ensuring healthier crop growth and higher yields.
Additionally, in the Agricultural Industry:
(4-CHLORO-3-METHYL-PHENOXY)-ACETIC ACID is also used as a plant growth regulator to stimulate root and shoot growth in certain crops. This dual functionality makes it a valuable tool in enhancing agricultural productivity and crop quality.
Proper handling and storage of (4-CHLORO-3-METHYL-PHENOXY)-ACETIC ACID are crucial to ensure the safety of agricultural workers and the environment, highlighting the importance of responsible chemical management in modern farming practices.

InChI:InChI=1/C9H9ClO3/c1-6-4-7(2-3-8(6)10)13-5-9(11)12/h2-4H,5H2,1H3,(H,11,12)

Upstream product

• 59-50-7 4-Chloro-3-methylphenol 
• 79-11-8 chloroacetic acid 
• 1643-15-8 2-(m-tolyloxy)acetic acid 
• 79-08-3 bromoacetic acid 
• 105-36-2 ethyl bromoacetate 
• 30406-61-2 ethyl 2-(4-chloro-3-methylphenoxy)acetate 
• 108-39-4 3-methyl-phenol 

Downstream Products

• 117554-55-9 Methyl 4-chloro-3-methylphenoxyacetate 
• 705-82-8 2-(4-chloro-3-methylphenoxy)ethanol 
• 416885-45-5 (4-chloro-5-methyl-2-nitro-phenoxy)-acetic acid 
• 81293-19-8 (4-Chloro-3-methyl-phenoxy)-acetic acid 2-acetyl-4-methyl-phenyl ester 
• 81293-21-2 (4-Chloro-3-methyl-phenoxy)-acetic acid 2-acetyl-5-methyl-phenyl ester 
• 345933-90-6 (4-Chloro-3-methyl-phenoxy)-acetic acid 2-acetyl-6-methyl-phenyl ester 
• 78613-20-4 2-Amino-5-(4'-chloro-3'-methylphenoxymethyl)-1,3,4-oxadiazole 
• 81293-17-6 (4-Chloro-3-methyl-phenoxy)-acetic acid 2-acetyl-phenyl ester 
• 39784-11-7 (4-chloro-3-methylphenoxy)-acetyl chloride 
• 118794-57-3 3-(4-chloro-3-methylphenoxymethyl)-4-amino-5-mercapto-1,2,4-triazole 
• 87657-94-1 [5-(4-Chloro-3-methyl-phenoxymethyl)-[1,3,4]oxadiazol-2-yl]-urea 
• 87657-97-4 1-[5-(4-Chloro-3-methyl-phenoxymethyl)-[1,3,4]oxadiazol-2-yl]-imidazolidine-2,4-dione 
• 87658-12-6 1-[5-(4-Chloro-3-methyl-phenoxymethyl)-[1,3,4]oxadiazol-2-yl]-5-[1-(4-chloro-phenyl)-meth-(Z)-ylidene]-imidazolidine-2,4-dione 

Relevant academic research and scientific papers

MODULATORS OF THE INTEGRATED STRESS RESPONSE PATHWAY

The present invention relates to compounds of formula (I) or pharmaceutically acceptable salts, solvates, hydrates, tautomers or stereoisomers thereof, wherein R1, R2, R2a, R3, Ra2, Ra4, R

Identification of 5-Substituted 2-Acylaminothiazoles That Activate Tat-Mediated Transcription in HIV-1 Latency Models

The persistent reservoir of cells latently infected with human immunodeficiency virus (HIV)-integrated proviral DNA necessitates lifelong suppressive antiretroviral therapy (ART). Epigenetic targeted compounds have shown promise as potential latency-reversing agents; however, these drugs have undesirable toxicity and lack specificity for HIV. We utilized a novel HEK293-derived FlpIn dual-reporter cell line, which quantifies specific HIV provirus reactivation (LTR promoter) relative to nonspecific host cell gene expression (CMV promoter), to identify the 5-substituted 2-acylaminothiazole hit class. Here, we describe the optimization of the hit class, defining the functionality necessary for HIV gene activation and for improving in vitro metabolism and solubility. The optimized compounds displayed enhanced HIV gene expression in HEK293 and Jurkat 10.6 latency cellular models and increased unspliced HIV RNA in resting CD4+ T cells isolated from HIV-infected individuals on ART, demonstrating the potential of the 2-acylaminothiazole class as latency-reversing agents.

The Novel 4-Phenyl-2-Phenoxyacetamide Thiazoles modulates the tumor hypoxia leading to the crackdown of neoangiogenesis and evoking the cell death

Tumor microenvironment is a complex multistep event which involves several hallmarks that transform the normal cell into cancerous cell. Designing the novel antagonistic molecule to reverse the tumor microenvironment with specific target is essential in modern biological studies. The novel 4-phenyl-2-phenoxyacetamide thiazole analogues 8a-ab were synthesized in multistep process, then screened and assessed for cytotoxic and anti-proliferative effects in vitro against multiple cancer cells of different origin such as MCF-7, A549, EAC and DLA cells which revealed that compound 8f with fluoro and methyl substitute has potential cytotoxic efficacy with an average IC50 value of ? 13 μM. The mechanism of cytotoxicity assessed for anti-tumor studies both in ascites and solid tumor models in-vivo inferred the regressed tumor activity. This is due to changes in the cause of tumor microenvironment with crackdown of neovascularization and evoking apoptosis process as assessed by CAM, corneal vascularization and apoptotic hallmarks in 8f treated cells. The molecular gene studies inferred involvement of HIF-1upregulation and stabilization of p53 which are interlinked in signaling as conferred by immunoblot analysis.

The anti-invasive role of novel synthesized pyridazine hydrazide appended phenoxy acetic acid against neoplastic development targeting matrix metallo proteases

Neoplastic metastasis is a major process where tumor cells migrate from the primary tumor and colonize at other parts of our body to form secondary tumor. Cancer incidences are rising and novel anti-neoplastic compounds with new mechanism of actions are essential for preventing cancer related deaths. In the current examination, a novel series of pyridazine analogues 6a-l was synthesized and evaluated against metastatic neoplastic cells. Experimental data postulated compound 6j has potential cytotoxic efficacy with prolonged activity against various cancer cells, including A549, HepG2, A498, CaSki and SiHa cells. Moreover, compound 6j arrests the A549 migration and invasions markedly by counteracting matrix metalloproteinase (MMP)-2 and MMP-9 expressions. Also, compound 6j proved its potentiality against Dalton's solid lymphoma progression in-vivo by abridging MVD and MMP expressions. Compound 6j interacts with MMP-2 and MMP-9 by H- bond in-silico, thereby down regulates the MMPs action in tumourigenesis. Altogether, we concluded that compound 6j down regulates MMP-2 and MMP-9 and thereby impairs metastatic cancer cell migration and invasions which can be translated into a potent anti-neoplastic agent.

Synthesis and Biological Activity of Ethyl 4-Alkyl-2-(2-(substituted phenoxy)acetamido)thiazole-5-carboxylate

(Chemical Equation Presented) A series of novel ethyl 4-(methyl or trifluoromethyl)-2-(2-(substituted phenoxy)acetamido)thiazole-5-carboxylates 7a, 7b, 7c, 7d, 7e and 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r were synthesized, and their structures were confirmed by IR, 1H-NMR, MS spectra and elemental analysis. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal activities. Compared with the fluorine free compounds 7a, 7b, and 7e, the compounds bearing fluorine 8g, 8j, and 8q showed higher herbicidal activities with 70-100% inhibition against Capsella bursa-pastoris, Amaranthus restroflexus, and Eclipta prostrata at the dosage of 150 g/ha, which indicated that the trifluoromethyl on the thiazole ring was beneficial for the herbicidal activity. Furthermore, compounds 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r were tested for fungicidal activity against Pseudoperonospora cubensis at 500 μg/mL. Compounds 8f and 8q showed the best fungicidal activity with more than 80% inhibition.

Synthesis and biological activity of 1-(Substituted phenoxyacetoxy)- 1-(pyridin-2-yl or thien-2-yl)methylphosphonates

A series of novel O,O-dimethyl 1-(substituted phenoxyacetoxy)-1-(pyridin-2-yl or thien-2-yl)methylphosphonates 6a-n and 7a-d were synthesized. Their structures were confirmed by IR, 1H NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal and fungicidal activities. For example, the title compounds 6a, 6c, 6l, 6m, and 7d possess 90-100% inhibition against most of the tested plants at the dosage of 1500 g ai/ha, whereas the title compounds 6b, 6g-h and 6n possess 92-100% inhibition against Fusarium oxysporum, Phyricularia grisea, Botrytis cinereapers, Gibberella zeae, Sclerotinia sclerotiorum, and Cercospora beticola at the concentration of 50mg/L.

Synthesis and herbicidal activity of 2-(Substituted phenoxyacetoxy)alkyl-5, 5-dimethyl-1,3,2-dioxaphosphinan-2-one

A series of 2-(substituted phenoxyacetoxy)alkyl-5,5-dimethyl-1,3,2- dioxaphosphinan-2-ones IIa-s were designed and synthesized on the basis of the previous work for the modification of alkylphosphonates I, and their structures were confirmed by 1H NMR, 31P NMR, 13C NMR, IR, MS, and elemental analysis. Their herbicidal activities against seven species of weeds were evaluated in a greenhouse. A part of the title compounds such as IIa-g, IIk, IIo, and IIr exhibited significant postemergence herbicidal activity against Abutilon theophrasti, Brassica juncea, Amaranthus retroflexus, and Eclipta prostrate at a dosage of 150 g ai/ha. Structure-activity relationship analyses indicated that the introduction of a phosphorus-containing heterocyclic ring had a favorable effect on herbicidal activity, and their herbicidal activity could be further increased by a reasonable combination of X, Y, and R in parent structure II. It could be found that the title compounds IIa 2-[(2,4-dichlorophenoxy)acetoxy](methyl)methyl-5,5-dimethyl-1,3, 2-dioxaphosphinan-2-one and IIr 2-[(4-chloro-2-methyl-phenoxy)acetoxy](methyl) methyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one possess high activity and a broad spectrum against all of the test broadleaf weeds with 70-100% inhibition effect at a dosage of 75 g ai/ha, and the title compounds IIa and IIr are safe for corn and wheat at a dosage of 150 g ai/ha. Furthermore, the title compound IIa possesses low rat toxicity. These results suggest that the title compounds IIa and IIr could be potential and selective postemergence herbicides for further development.

Studies on the synthesis of bis-quaternary ammonium salts of geometrical isomers and its potential as bioregulators

Tertiary amine N,N-dimethyl-2-nitrophenylmethanamine 4 prepared from 2-nitrobenzaldehyde 3 by Leuckart's reaction and (3-N,N-diethylamino-2- hydroxypropyl)-3-(3-nitrophenyl) prop-2-en-oate 9 and 3-(diethylamino)-2- hydroxypropyl 2-(4-chloro-3-methylphenoxy)acetate 14 prepared through the formation of glycidyl ester have been reacted with dichlorides of maleic acid and fumaric acid, which in turn have been prepared by reacting these acids with thionyl chloride to get bis-quaternary ammonium salts 1a-c and 2a-c. The synthesized salts 1a-c and 2a-c are tested on rice (Oryza sativa, PR-114) for their biological activity. All the tested compounds are found to possess good plant growth retardant activity. Compound 2c is found to be the best plant growth retardant among the six newly synthesized compounds.

Studies of O,O-Dimethyl α-(2,4-Dichlorophenoxyacetoxy) ethylphosphonate (HW02) as a new herbicide. 1. Synthesis and herbicidal activity of HW02 and analogues as novel inhibitors of pyruvate dehydrogenase complex

On the basis of the previous work for optimization of O,O-diethyl α-(substituted phenoxyacetoxy)alkylphosphonates, further extensive syntheticmodifications were made to the substituents in alkylphosphonate and phenoxymoieties of the title compounds. New O,O-dimethyl α-(substituted phenoxyacetoxy)alkylphosphonates were synthesized as potential inhibitors of pyruvate dehydorogenase complex (PDHc). Their herbicidal activity and efficacy in vitro against PDHc were examined. Some of these compounds exhibited significant herbicidal activity and were demonstrated to be effective inhibitors of PDHc from three different plants. The structure-activity relationships of these compounds including previously reported analogous compoundswere studied by examining their herbicidal activities. Both inhibitory potency against PDHc and herbicidal activity of title compounds could be increased greatly by optimizing substituent groups of the title compounds. O,O-Dimethyl α-(2,4- dichlorophenoxyacetoxy)ethylphosphonate (I-5), which acted as a competitive inhibitor of PDHc with much higher inhibitory potency against PDHc from Pisum sativum and Phaseolus radiatus than from Oryza sativa, was found to be themost effective compound against broadleaf weeds and showed potential utility as herbicide.