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Related Concept Videos

Structure-Activity Relationships and Drug Design01:28

Structure-Activity Relationships and Drug Design

Drug design is a dynamic field that involves discovering and developing new medications based on specific biological targets. This process heavily relies on structure-activity relationships (SAR) and quantitative structure-activity relationships (QSAR) to guide the design and optimization of efficient drugs.
SAR studies the intricate relationship between a drug's chemical structure and biological activity. It focuses on understanding how modifications to a drug's structure can influence its...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...

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Related Experiment Video

Updated: Jun 3, 2026

Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
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Published on: June 23, 2019

From Rational Design to Bioactivity Enhancement: Novel Benzofuranone Insecticide Discovery Assisted by a

Renxuan Zou1,2, Jinyang Zhou1,2, Ziyan Yang1,2

  • 1Innovation Center of Pesticide Research, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, People's Republic of China.

Journal of Agricultural and Food Chemistry
|June 2, 2026
PubMed
Summary

Novel benzofuranone compounds show insecticidal activity against aphids. Complexing with calix[4]arene (C4A) enhanced efficacy and solubility, offering a safer alternative for pest control.

Keywords:
benzofuranonecalix[4]areneinsecticidal activitysupramolecular synergistswater solubility

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Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

Area of Science:

  • Agricultural Chemistry
  • Organic Chemistry
  • Toxicology

Background:

  • Developing novel insecticidal agents targeting nicotinic acetylcholine receptors (nAChR) is crucial for sustainable agriculture.
  • Existing insecticides face challenges with resistance and environmental impact.

Purpose of the Study:

  • To design and synthesize novel benzofuranone derivatives as potential insecticidal agents.
  • To investigate the insecticidal efficacy and mechanism of action of a lead compound.
  • To enhance the solubility and insecticidal activity of the lead compound using supramolecular complexation.

Main Methods:

  • Synthesis of novel benzofuranone compounds.
  • Bioassays against Myzus persicae and Aphis glycines to determine mortality rates and LC50 values.
  • Molecular docking to understand interactions with target residues (TRP143 and TYR186).
  • Formation of a supramolecular complex using calix[4]arene (C4A) and the lead compound (5i).
  • Evaluation of the enhanced insecticidal activity and solubility of the C4A@5i complex.
  • Assessment of ecotoxicity, particularly towards bees.

Main Results:

  • Several benzofuranone compounds demonstrated insecticidal activity against M. persicae and A. glycines (30-80% mortality).
  • Compound 5i showed the best bioactivity (LC50 = 106.86 μg/mL for M. persicae, 43.94 μg/mL for A. glycines), attributed to π-π interactions with TRP143 and TYR186.
  • The supramolecular complex C4A@5i significantly enhanced insecticidal activity (LC50 = 56.66 μg/mL for M. persicae, 26.98 μg/mL for A. glycines) due to a 6.27-fold increase in solubility.
  • Compound 5i, C4A, and C4A@5i exhibited low toxicity to bees.

Conclusions:

  • Novel benzofuranone derivatives show promise as effective insecticidal agents.
  • Supramolecular complexation with calix[4]arene is a viable strategy to improve the solubility and insecticidal efficacy of benzofuranone compounds.
  • The developed supramolecular insecticide C4A@5i offers a potentially safer and more effective pest control solution with low bee toxicity.