91085-56-2

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 3,5-DICHLOROBENZOATE is used as a synthetic intermediate for the production of various pharmaceuticals. It plays a crucial role in the synthesis of active pharmaceutical ingredients, contributing to the development of new drugs and medications.
Used in Pesticide Industry:
In the pesticide industry, ETHYL 3,5-DICHLOROBENZOATE serves as a key intermediate in the synthesis of various agrochemicals. Its use in this sector helps in the development of effective and efficient pesticides for agricultural and horticultural applications.
Used in Organic Compounds Synthesis:
ETHYL 3,5-DICHLOROBENZOATE is also utilized as an intermediate in the synthesis of other organic compounds. Its versatile chemical properties make it a valuable component in the production of a wide range of organic substances for various applications.
It is important to handle and store ETHYL 3,5-DICHLOROBENZOATE with proper safety precautions, as it is considered hazardous and can cause irritation to the skin, eyes, and respiratory system if not handled carefully.

InChI:InChI=1/C9H8Cl2O2/c1-2-13-9(12)6-3-7(10)5-8(11)4-6/h3-5H,2H2,1H3

Upstream product

• 64-17-5 ethanol 
• 51-36-5 3,5-dichlorobenzoic acid 
• 19752-55-7 1-bromo-3,5-dichlorobenzene 
• 2905-62-6 3,5-dichlorobenzoyl chloride 

Downstream Products

• 2905-67-1 methyl 3,5-dichlorobenzoate 
• 1309790-93-9 ethyl 3-allyl-5-chlorobenzoate 
• 62899-78-9 3,5-dichlorobenzoic acid hydrazide 
• 1220286-49-6 N-[(4Z)-4-[[(6-chloro-3-pyridinyl)methyl]ethylamino]-3-methyl-5-nitro-1,2,3,6-tetrahydropyrimidin-1-yl]-3,5-dichlorobenzamide 
• 68496-91-3 5-(3,5-dichloro-phenyl)-[1,3,4]oxadiazole-2-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Design, Synthesis, and Study of the Insecticidal Activity of Novel Steroidal 1,3,4-Oxadiazoles

A series of novel steroidal derivatives with a substituted 1,3,4-oxadiazole structure was designed and synthesized, and the target compounds were evaluated for their insecticidal activity against five aphid species. Most of the tested compounds exhibited potent insecticidal activity against Eriosoma lanigerum (Hausmann), Myzus persicae, and Aphis citricola. Compounds 20g and 24g displayed the highest activity against E. lanigerum, showing LC50 values of 27.6 and 30.4 μg/mL, respectively. Ultrastructural changes in the midgut cells of E. lanigerum were detected by transmission electron microscopy, indicating that these steroidal oxazole derivatives might exert their insecticidal activity by destroying the mitochondria and nuclear membranes in insect midgut cells. Furthermore, a field trial showed that compound 20g exhibited effects similar to those of the positive controls chlorpyrifos and thiamethoxam against E. lanigerum, reaching a control rate of 89.5% at a dose of 200 μg/mL after 21 days. We also investigated the hydrolysis and metabolism of the target compounds in E. lanigerum by assaying the activities of three insecticide-detoxifying enzymes. Compound 20g at 50 μg/mL exhibited inhibitory action on carboxylesterase similar to the known inhibitor triphenyl phosphate. The above results demonstrate the potential of these steroidal oxazole derivatives to be developed as novel pesticides.

4-Alkyl-1,2,4-triazole-3-thione analogues as metallo-β-lactamase inhibitors

In Gram-negative bacteria, the major mechanism of resistance to β-lactam antibiotics is the production of one or several β-lactamases (BLs), including the highly worrying carbapenemases. Whereas inhibitors of these enzymes were recently marketed, they only target serine-carbapenemases (e.g. KPC-type), and no clinically useful inhibitor is available yet to neutralize the class of metallo-β-lactamases (MBLs). We are developing compounds based on the 1,2,4-triazole-3-thione scaffold, which binds to the di-zinc catalytic site of MBLs in an original fashion, and we previously reported its promising potential to yield broad-spectrum inhibitors. However, up to now only moderate antibiotic potentiation could be observed in microbiological assays and further exploration was needed to improve outer membrane penetration. Here, we synthesized and characterized a series of compounds possessing a diversely functionalized alkyl chain at the 4-position of the heterocycle. We found that the presence of a carboxylic group at the extremity of an alkyl chain yielded potent inhibitors of VIM-type enzymes with Ki values in the μM to sub-μM range, and that this alkyl chain had to be longer or equal to a propyl chain. This result confirmed the importance of a carboxylic function on the 4-substituent of 1,2,4-triazole-3-thione heterocycle. As observed in previous series, active compounds also preferentially contained phenyl, 2-hydroxy-5-methoxyphenyl, naphth-2-yl or m-biphenyl at position 5. However, none efficiently inhibited NDM-1 or IMP-1. Microbiological study on VIM-2-producing E. coli strains and on VIM-1/VIM-4-producing multidrug-resistant K. pneumoniae clinical isolates gave promising results, suggesting that the 1,2,4-triazole-3-thione scaffold worth continuing exploration to further improve penetration. Finally, docking experiments were performed to study the binding mode of alkanoic analogues in the active site of VIM-2.

4-Amino-1,2,4-triazole-3-thione-derived Schiff bases as metallo-β-lactamase inhibitors

Resistance to β-lactam antibiotics in Gram-negatives producing metallo-β-lactamases (MBLs) represents a major medical threat and there is an extremely urgent need to develop clinically useful inhibitors. We previously reported the original binding mode of 5-substituted-4-amino/H-1,2,4-triazole-3-thione compounds in the catalytic site of an MBL. Moreover, we showed that, although moderately potent, they represented a promising basis for the development of broad-spectrum MBL inhibitors. Here, we synthesized and characterized a large number of 4-amino-1,2,4-triazole-3-thione-derived Schiff bases. Compared to the previous series, the presence of an aryl moiety at position 4 afforded an average 10-fold increase in potency. Among 90 synthetic compounds, more than half inhibited at least one of the six tested MBLs (L1, VIM-4, VIM-2, NDM-1, IMP-1, CphA) with Ki values in the μM to sub-μM range. Several were broad-spectrum inhibitors, also inhibiting the most clinically relevant VIM-2 and NDM-1. Active compounds generally contained halogenated, bicyclic aryl or phenolic moieties at position 5, and one substituent among o-benzoic, 2,4-dihydroxyphenyl, p-benzyloxyphenyl or 3-(m-benzoyl)-phenyl at position 4. The crystallographic structure of VIM-2 in complex with an inhibitor showed the expected binding between the triazole-thione moiety and the dinuclear centre and also revealed a network of interactions involving Phe61, Tyr67, Trp87 and the conserved Asn233. Microbiological analysis suggested that the potentiation activity of the compounds was limited by poor outer membrane penetration or efflux. This was supported by the ability of one compound to restore the susceptibility of an NDM-1-producing E. coli clinical strain toward several β-lactams in the presence only of a sub-inhibitory concentration of colistin, a permeabilizing agent. Finally, some compounds were tested against the structurally similar di-zinc human glyoxalase II and found weaker inhibitors of the latter enzyme, thus showing a promising selectivity towards MBLs.

Synthesis and bioactivity of sulfide derivatives containing 1,3,4-oxadiazole and pyridine

A series of novel sulfide derivatives containing 1,3,4-oxadiazole and pyridine were synthesized, characterized, and tested for their antibacterial activity against tobacco bacterial wilt and rice bacterial blight and for insecticidal activity toward diamondback moth. The results showed that some compounds had good insecticidal and bactericidal activity, e.g., the activities of compounds 6e and 6g–6j toward tobacco bacterial wilt were much better than those of commercial thiodiazole-copper, and some of the synthesized compounds possessed good insecticidal activity against Plutella xylostella. Compounds 6d, 6h, 6j, 6l, 6p, 6r, and 6p displayed over 93% activity at 500 mg L? 1.

Synthesis of novel indole derivatives containing double 1,3,4-oxadiazole moiety as efficient bactericides against phytopathogenic bacterium Xanthomonas oryzae

Abstract: A series of novel indole derivatives containing double 1,3,4-oxadiazole moiety was designed, synthesized and evaluated for their antibacterial activities in vitro. These compounds were fully characterized by 1H NMR, 13C NMR, and HRMS. Bioassay results indicated that most of title compounds exhibited excellent antibacterial activities against rice bacterial pathogen Xanthomonas oryzae (Xoo). For example, compounds 7d, 7h, 7i, 7j, 7k, 7l and 7m had the half-maximal effective concentration (EC50) values of 52.31, 54.12, 40.65, 38.80, 51.13, 52.75 and 50.66?μg/mL, respectively, which was better than that of commercial product bismerthiazol (BMT) (85.18?μg/mL). The experimental results proved that indole derivatives bearing double 1,3,4-oxadiazole unit are promising candidates for the development of new agricultural bactericides against pathogenic bacterium Xoo. Graphical abstract: [Figure not available: see fulltext.].

Design, synthesis, insecticidal activity and 3D-QSR study for novel trifluoromethyl pyridine derivatives containing an 1,3,4-oxadiazole moiety

A series of trifluoromethyl pyridine derivatives containing 1,3,4-oxadiazole moiety was designed, synthesized and bio-assayed for their insecticidal activity. The result of bio-assays indicated the synthesized compounds exhibited good insecticidal activity against Mythimna separata and Plutella xylostella, most of the title compounds show 100% insecticidal activity at 500 mg L-1 and >80% activity at 250 mg L-1 against the two pests. Compounds E18 and E27 showed LC50 values of 38.5 and 30.8 mg L-1 against Mythimna separata, respectively, which were close to that of avermectin (29.6 mg L-1); compounds E5, E6, E9, E10, E15, E25, E26, and E27 showed 100% activity at 250 mg L-1, which were better than chlorpyrifos (87%). CoMFA and CoMSIA models with good predictability were proposed, which revealed the electron-withdrawing groups with an appropriate bulk at 2- and 4-positions of benzene ring could enhance insecticidal activity.

Synthesis and anti-inflammatory activity of hydrazones bearing biphenyl moiety and vanillin based hybrids

The intense research work in the field of medicinal chemistry has enhanced the significance of Biphenyl moiety as pharmacologically important compound. Some of the compounds bearing Biphenyl moiety possess important medicinal properties like antihypertensive and calcium channel blocker, anti-inflammatory, diuretic, anti-diabetic activity, antipsychotic and anxiolytic activity. The present article describes the synthesis of novel benzohydrazides and 2-phenylacetohydrazides bearing Biphenyl moiety and vanillin hybrid. The synthesized compounds (31-40) were characterized by 1H NMR, Mass and IR spectroscopic techniques and were evaluated for anti-inflammatory activity by carrageenan paw edema method. The results of the study revealed that compounds 39 and 40 (bearing 2-(4-nitrophenyl)acetohydrazide and 2-(2,3-dihydrobenzofuran-5-yl)acetohydrazide) showed maximum anti-inflammatory activity while the compounds 31, 32, 33, 34 and 38 bearing benzohydrazides displayed moderate anti-inflammatory activity.

Synthesis of novel benzohydrazides bearing 4-[3-methyl-4-(methylsulfonyl)pyridin-2-yl] moiety as potential antibacterial agents

This work reports the synthesis and antibacterial activity of novel hydrazone derivatives 8a-k bearing 4-[3-methyl-4-(methylsulfonyl)pyridin- 2-yl] moiety. Spectroscopic techniques like 1H NMR, mass and IR tools was utilized for the characterization of these hydrazone derivatives. The synthesized hydrazone derivatives were tested against a set of bacterial strains, namely, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Streptococcus pyogenes by paper disc diffusion method. Compounds 8b, 8d, 8e, 8f, 8h, 8i showed good antibacterial activity against the test organisms.

Synthesis, characterization and antimicrobial evaluation of novel (E)-N′-(4-(1-((3,4-dimethoxypyridin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)benzylidene)benzohydrazide derivatives

The synthesis of novel 1,2,3-triazole-hydrazone derivatives embedded with 3,4-dimethoxy pyridine ring nucleus is described. These derivatives were prepared utilizing, 2-(chloromethyl)-3,4-dimethoxypyridine 1, 4-ethynylbenzaldehye 5 and various benzohydrazides7a-7j. The structures of the newly synthesized 1,2,3-triazole-hydrazones 8a-j was established on the basis of the spectroscopic techniques like 1H NMR, mass and IR data. They were evaluated against a panel of bacterial and fungal pathogens such as Staphylococcus. pyogens, Staphylococcus. Aureus (Gram positive bacteria), Escherichia.coli, Pseudomonas. aeruginosa (Gram negative bacteria) and Aspergillus niger and Candida albicans (Fungal stains). Compounds 8b, 8c, 8d, 8e and 8f with R = 4-OH, 4-OMe, 4-SO2Me, 3,45,-OMe and 3-NO2 respectively showed moderate antibacterial activity while compounds 8b, 8d, 8i and 8j with R = 4-OH, 4-SO2Me, 3,5-dichloro and 2,5-difluoro substitution exhibited very good fungal activity.

Synthesis and antibacterial activity of some new quinaxaline-benzohydrazides

Quinoxalines have been found to exhibit various biological activities such as antibacterial, antifungal, anti-tubercular, anxiolytic, anticancer, antioxidant, anti-inflammatory, anti-HIV, antihelmintic and anticonvulsant. The present study aims towards synthesis, characterization and determination of antimicrobial susceptibility testing of various novel quinoxaline derivatives. The quinoxaline-benzohydrazides 6a-m have been obtained by the condensation of quinoxaline-2-carboxaldehyde 4 with various benzohydrazides 5a-m in ethanol at reflux temperature. All the newly synthesized quinoxaline-benzohydrazide derivatives have been characterized by 1H NMR, IR and mass spectroscopic analysis. The synthesized quinoxaline-benzohydrazides 6a-m have been screened for antibacterial activity. Most of the compounds show significant antibacterial activity.