Synthesis and insecticidal activities of <i>O,O</i>-dialkyl-2-[3-bromo-1-(3-chloropyridin-2-yl)-1<i>H</i>-pyrazole-5-carbonyloxy] (aryl) methylphosphonates

Wang, Wei; Lie-ping, Wang; Ning, Bin-Ke; Mao, Ming‐Zhen; Xue, Chao; Wang, Haiyang

doi:10.1080/10426507.2016.1206103

Cited by 12 publications

(14 citation statements)

References 9 publications

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“…The larvicidal activities of compounds I , II , and chlorantraniliprol were determined according the reference methods . The insecticial activity against M. separata was tested by foliar application; individual corn (Tangyu10, Zea mays L .)…”

Section: Methodsmentioning

confidence: 99%

“…In our previous work, some series of novel N ‐pyridylpyrazole derivatives were designed and synthesized, and the ensuing bioassay results exhibited excellent larvicidal activity against Mythimna separata and Plutella xylostella in some cases . On the other hand, among various biologically scaffolds, diacylhydrazine and 1,3,4‐oxadiazole moieties have occupied important positions in pesticide chemistry and are often introduced in the design of bioactive compounds.…”

Section: Introductionmentioning

confidence: 99%

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

Wang

Zheng

Huang

et al. 2019

Journal of Heterocyclic Chem

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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.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

Wang

Zheng

Huang

et al. 2019

Journal of Heterocyclic Chem

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“…Pyrazole being a heterocyclic moiety have played a major role in agro chemistry. Cyantraniliprole, Chlorantraniliprole and Pyriprole are one of those pyrazolederivates that are available in market as commercial pesticides [62]. Involvement of EcR-USP (ecdysone receptorultraspiracle protein) heterodimeric receptors in molting has coaxed the pharmacists towards the synthesis of potent EcR-USP based ligands to assist and enhance the ecdysis in environmental friendly insects.…”

Section: Insecticidal Activitymentioning

confidence: 99%

Pyrazole Bearing Molecules as Bioactive Scaffolds: A Review

Aziz

Zahoor

Ahmad

2020

J. Chil. Chem. Soc.

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Pyrazole being a heterocyclic motif has secured an eccentric status in the field of medicinal chemistry. Pyrazole and its derivatives have tremendous biological applications like anti-cancer, anti-microbial, antiviral, antifungal, anti-inflammatory, analgesic, insecticidal etc. In this review, some recent developments have been reported for the synthesis of biologically active pyrazole based molecules having biological potential such as anti-SIRT1 and SIRT2, anti-FAAH, anti-NOSs, as liver X receptor partial agonist, CB2 receptor ligand and glucagon receptor antagonists.

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“…The synthesis of α-acyloxyphosphonates 8 is one of the most thoroughly studied transformations of α-hydroxyphosphonates 1 . α-Acyloxyphosphonates 8 attracted attention as potential herbicides [ 69 , 70 , 71 ], fungicides [ 69 ], and insecticides [ 72 ]. A number of articles reported the acylation of α-hydroxyphosphonates 1 with carboxylic acid chlorides in the presence of triethylamine [ 73 , 74 , 75 ] or pyridine [ 76 , 77 ] as the hydrochloric acid scavenger.…”

Section: Reactions Of α-Hydroxyphosphonatesmentioning

confidence: 99%

Synthesis and Reactions of α-Hydroxyphosphonates

Rádai

Keglevich

2018

Molecules

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This review summarizes the main synthetic routes towards α-hydroxyphosphonates that are known as enzyme inhibitors, herbicides and antioxidants, moreover, a number of representatives express antibacterial or antifungal effect. Special attention is devoted to green chemical aspects. α-Hydroxyphosphonates are also versatile intermediates for other valuable derivatives. O-Alkylation and O-acylation are typical reactions to afford α-alkoxy-, or α-acyloxyphosphonates, respectively. The oxidation of hydroxyphosphonates leads to ketophosphonates. The hydroxy function at the α carbon atom of hydroxyphosphonates may be replaced by a halogen atom. α-Aminophosphonates formed in the nucleophilic substitution reaction of α-hydroxyphosphonates with primary or secondary amines are also potentially bioactive compounds. Another typical reaction is the base-catalyzed rearrangement of α-hydroxy-phosphonates to phosphates. Hydrolysis of the ester function of hydroxyphosphonates leads to the corresponding phosphonic acids.

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Synthesis and insecticidal activities of O,O-dialkyl-2-[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyloxy] (aryl) methylphosphonates

Cited by 12 publications

References 9 publications

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

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

Pyrazole Bearing Molecules as Bioactive Scaffolds: A Review

Synthesis and Reactions of α-Hydroxyphosphonates

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