2381-75-1

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
(4-CHLORO-PHENOXY)-ACETIC ACID HYDRAZIDE is used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals for its ability to be a key component in the development of new drugs and agricultural products.
Used in Plant Growth Regulation:
(4-CHLORO-PHENOXY)-ACETIC ACID HYDRAZIDE is used as a plant growth regulator to stimulate cell division and promote elongation growth in plants, enhancing their overall growth and development.
Used in Agriculture:
In the agricultural industry, (4-CHLORO-PHENOXY)-ACETIC ACID HYDRAZIDE is used to control pre-harvest drop, helping to prevent the premature falling of fruits, and to encourage fruit thinning in apples and pears, which can lead to a higher quality and more marketable yield.
Used in Medical Research:
(4-CHLORO-PHENOXY)-ACETIC ACID HYDRAZIDE is used in research for potential applications in the treatment of hypothyroidism and neurodegenerative diseases, due to its unique chemical properties and biological activity.

InChI:InChI=1/C8H9ClN2O2/c9-6-1-3-7(4-2-6)13-5-8(12)11-10/h1-4H,5,10H2,(H,11,12)

Upstream product

• 14426-42-7 ethyl p-chlorophenoxyacetate 
• 122-88-3 4-Chlorophenoxyacetic acid 
• 106-48-9 4-chloro-phenol 
• 7803-57-8 hydrazine hydrate 
• 105-39-5 chloroacetic acid ethyl ester 
• 4841-22-9 (4-chloro-phenoxy)-acetic acid methyl ester 

Downstream Products

• 105907-43-5 (4-chloro-phenoxymethyl)-carbamic acid isopropyl ester 
• 102653-23-6 (4-chloro-phenoxymethyl)-carbamic acid-(2-chloro-ethyl ester) 
• 52095-04-2 4-Chlorphenoxy-essigsaeureisopropylidenhydrazid 
• 21520-97-8 5-(4-chloro-phenoxymethyl)-[1,3,4]oxadiazol-2-ylamine 
• 84160-95-2 2-(4-chlorophenoxy)-N-(1,3-dioxo-1,3-dihydroisoindol-2-yl)acetamide 
• 125298-99-9 (4-Chloro-phenoxy)-acetic acid [2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-hydrazide 
• 84816-33-1 (4-Chloro-phenoxy)-acetic acid [5-bromo-2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-hydrazide 
• 77869-90-0 2-[2-(4-Chloro-phenoxy)-acetyl]-5-methyl-2,4-dihydro-pyrazol-3-one 
• 68212-26-0 3-(4'-chlorophenoxymethyl)-N⁴-phenyl-5-mercapto-1,2,4-triazole 
• 97942-31-9 2-Chloromethyl-5-(4-chloro-phenoxymethyl)-[1,3,4]oxadiazole 
• 113603-99-9 Chloro-acetic acid N'-[2-(4-chloro-phenoxy)-acetyl]-hydrazide 
• 120513-06-6 1-(p-chlorophenoxyacetyl)-2-phenylsulfonylhydrazine 
• 34088-34-1 C₁₅H₁₅ClN₂O₄S 
• 130946-73-5 potassium (2-(4-chlorophenoxy)acetylhydrazinyl)dithioformate 

Relevant academic research and scientific papers

Molecular docking and synthesis of caffeic acid analogous and its anti-inflammatory, analgesic and ulcerogenic studies

A series of caffeic acid (CA) derivatives 7a-j were synthesized via etherification and coupling action and their chemical structures were elucidated spectroscopically. Motivated by the various biological activities displayed by CA derivatives such as anti-inflammatory, antiviral, anticancer and antioxidant and also based on its extensively consumption in the human diet. In the present work, the newly synthesized compounds 7a-j were evaluated for anti-inflammatory and analgesic action and most of them exerted comparable activity to the reference compound celecoxib. Further, ulcer indexes for the most active compounds were calculated and most of them showed less ulcerogenic effect than the reference drug. Among the title series 7a-j, compounds 7f and 7g with electron withdrawing bromo and chloro group respectively, at the para position of the phenoxy ring was showed good activity compared to all other compounds. Interestingly, the COX-I/COX-II activity ratio of potent compounds 7f and7g showed an almost equal inhibitory effect on both isoenzymes. Further, molecular docking studies have been performed for the potent compounds which showed statistically significant result.

Synthesis and characterization of biologically important quinoline incorporated triazole derivatives

Triazoles are well recognized in literature for their significant biologically active heterocyclic compounds. Also the quinoline nucleus found in several natural products shows a varied biological activity. Keeping in the view of these observations, a novel series of 6/7/8-substtuted-2-[(5-((4-chlorophenoxy)methyl)-4H-1,2,4-triazol-3-yl)thio]quinoline-3-carbaldehydes and 6/7/8-substituted-2-[(5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio]quinoline-carbaldehydes were synthesized by the condensation of 5-(4-chloro phenoxy methyl)-2,4-dihydro-1,2,4-triazole-3-thiones and 5-(pyridin-3-yl)-4H-1,2,4-triazole-3-thiols with 6/7/8-substituted-2-chloro quinoline-3-carbaldehydes. The new series were established by Mass, NMR and IR spectroscopy and were also screened for their antimicrobial activities. A few of the novel compounds exhibited tremendous bioactivities compared to that of normal drug.

Expedient discovery for novel antifungal leads: 1,3,4-Oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment

Developing novel fungicide candidates are intensively promoted by the rapid emergences of resistant fungi that outbreak on agricultural production. Aiming to discovery novel antifungal leads, a series of 1,3,4-oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment were constructed for evaluating their inhibition effects against phytopathogenic fungi in vitro and in vivo. Systematically structural optimizations generated the bioactive molecule I32 that was identified as a promising inhibitor against Rhizoctonia solani with the in vivo preventative effect of 58.63% at 200 μg/mL. The observations that were captured by scanning electron microscopy and transmission electron microscopy demonstrated that the bioactive molecule I32 could induce the sprawling growth of hyphae, the local shrinkage and rupture on hyphal surfaces, the extreme swelling of vacuoles, the striking distortions on cell walls, and the reduction of mitochondria numbers. The above results provided an indispensable complement for the discovery of antifungal lead bearing a quinazolin-4(3H)-one and 1,3,4-oxadiazole fragment.

N-Amino-1,8-Naphthalimide is a Regenerated Protecting Group for Selective Synthesis of Mono-N-Substituted Hydrazines and Hydrazides

A new route to synthesis of various mono-N-substituted hydrazines and hydrazides by involving in a new C?N bond formation by using N-amino-1,8-naphthalimide as a regenerated precursor was invented. Aniline and phenylhydrazines are reproduced upon reacting these individually with 1,8-naphthalic anhydride followed by hydrazinolysis. The practicality and simplicity of this C?N dihalo alkanes; developed a synthon for bond formation protocol was exemplified to various hydrazines and hydrazides. N-amino-1,8-naphthalimide is suitable synthon for transformation for selective formation of mono-substituted hydrazine and hydrazide derivatives. Those are selective mono-amidation of hydrazine with acid halides; mono-N-substituted hydrazones from aldehydes; synthesis of N-aminoazacycloalkanes from acetohydrazide scaffold and inserted to hydroxy derivatives; distinct synthesis of N,N-dibenzylhydrazines and N-benzylhydrazines from benzyl halides; synthesis of N-amino-amino acids from α-halo esters. Ecofriendly reagent N-amino-1,8-naphthalimide was regenerated with good yields by the hydrazinolysis in all procedures.

Identification of a Novel Oxadiazole Inhibitor of Mammalian Target of Rapamycin

We performed a biochemical screen against mTOR using in-house small molecule library. Two novel, structurally distinct hits were identified. Among them, a novel oxadiazole scaffold compound (2) suppressed the phosphorylation of both S6K1 and Akt1 in HeLa cells. Docking study suggested that 2 is ATP-competitive and shows a pi-pi interaction with Trp2239 and hydrogen bonds with Trp2239 and Thr2245. Through derivatization, a slightly more potent analogue (2a) was identified with IC50 of 9.6 μM. Our study provides a starting point for discovery of novel potent mTOR inhibitors.

Synthesis and Insecticidal Evaluation of Novel N-pyridylpyrazole Derivatives Containing Diacylhydrazine/1,3,4-Oxadiazole Moieties

Two series of novel N-pyridylpyrazole derivatives containing diacylhydrazine/1,3,4-oxadiazole moieties were designed and synthesized based on the structure of chlorantraniliprole and characterized via 1H-NMR, 13C-NMR, IR, MS, and elemental analysis. The preliminary bioassay indicated that some of the title compounds I and II exhibited larvicidal activities against Mythimna separata with 90–100% death rates at 500?mg/L. The further test showed that these compounds had weak insecticidal activity against Mythimna separata and Plutella xylostella at 200?mg/L and might be not suitable as insecticide lead compound for further optimization.

Synthesis and luminescence properties of novel 8-hydroxyquinoline derivatives and their Eu(III) complexes

Six novel 8-hydroxyquinoline derivatives were synthesized using 2-methyl-8-hydroxyquinoline and para-substituted phenol as the main starting materials, and were characterized by 1H nuclear magnetic resonance (NMR), mass spectrometry (MS), ultraviolet (UV) light analysis and infra-red (IR) light analysis. Their complexes with Eu(III) were also prepared and characterized by elemental analysis, molar conductivity, UV light analysis, IR light analysis, and thermogravimetric–differential thermal analysis (TG–DTA). The results showed that the ligand coordinated well with Eu(III) ions and had excellent thermal stability. The structure of the target complex was EuY1–6(NO3)3.2H2O. The luminescence properties of the target complexes were investigated, the results indicated that all target complexes had favorable luminescence properties and that the introduction of an electron-donating group could enhance the luminescence intensity of the corresponding complexes, but the addition of an electron-withdrawing group had the opposite effect. Among all the target complexes, the methoxy-substituted complex (–OCH3) had the highest fluorescence intensity and the nitro-substituted complex (–NO2) had the weakest fluorescence intensity. The results showed that 8-hydroxyquinoline derivatives had good energy transfer efficiency for the Eu(III) ion. All the target complexes had a relatively high fluorescence quantum yield. The fluorescence quantum yield of the complex EuY3(NO3)3.2H2O was highest among all target complexes and was up to 0.628. Because of excellent luminescence properties and thermal stabilities of the Eu(III) complexes, they could be used as promising candidate luminescent materials.

Synthesis and biological evaluations of some new oxadiazole–piperidine hybrid derivatives as antioxidant agents

A series of some new 1,3,4-oxadiazole-2-thiol derivatives (6a-h) containing cyclic secondary amine such as piperidine ring was expeditiously synthesized by alkylation of 1,3,4-oxadiazol-2-thiol derivatives with chloroethyl piperidine hydrochloride. The 1,3,4-oxadiazole-2-thiols were effectively synthesized by cyclization reaction of acid hydrazide derivatives with carbon disulfide. The target compounds 6a-h were preliminarily screened for in vitro antioxidant activities using various in vitro antioxidant assays including 2,2′-diphenyl-1-picrylhydrazyl, nitric oxide, and hydrogen peroxide methods. The results showed that the compounds exhibited promising antioxidant property in the three methods at 50, 75, and 100 μM. Among the tested compounds, the compounds 6a and 6b having chloro substituent in the benzene ring displayed greater radical scavenging activity.

A 1, 2, 4 - triazole thioether derivative and its preparation and use

The invention discloses a 1,2,4-triazolothio-ether derivative as well as a preparation and an application thereof. The compound with the concentration being 10 mu g/mL has better inhibition property on pythium ultimum trow, and the inhibition rate is up t

Synthesis and larvicidal activity of 1,3,4-oxadiazole derivatives containing a 3-chloropyridin-2-yl-1H-pyrazole scaffold

Abstract: A new series of 1,3,4-oxadiazole derivatives with a 3-chloropyridin-2-yl-1H-pyrazole moiety was designed, synthesized, and characterized. The results of bioassay against Helicoverpa armigera and Plutella xylostella indicated that some of the synthesized compounds showed remarkable larvicidal activity. In particular, the LC50 values of the most active compounds against P. xylostella were 46.5, 23.9, and 13.9?mg/dm3, and against Helicoverpa armigera were 88.3 and 69.5?mg/dm3, the latter being slightly better than commercial chlorpyrifos (LC50 103.77?mg/dm3). Preliminary SAR was also discussed. Graphical abstract: [Figure not available: see fulltext.].