Structural optimization based on 4,5-dihydropyrazolo[1,5-a]quinazoline scaffold for improved insecticidal activities

Yang, Shuai; Li, Benjie; Tang, Jiahong; Peng, Hongxiang; Pu, Chunmei; Zhao, Chen; Xu, Hanhong

doi:10.1016/j.pestbp.2023.105533

Cited by 4 publications

(2 citation statements)

References 49 publications

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“…This solvent-thermal method has advantages over reported methods for synthesizing ester derivatives, where esterification reactions are conducted in oil baths, including faster reaction rates, higher purity, specific reaction pathways, and green synthesis. To our knowledge, this strategy has not been applied to the synthesis of PEs . − This green synthesis method is generally applicable for preparing ester derivatives by varying different alkyl alcohol substrates, representing a significant advancement in obtaining more phenylpyrazole esterified heterocyclic compounds. Given this novel approach, we adopted the general synthetic route outlined in Scheme .…”

Section: Resultsmentioning

confidence: 99%

Design, One-Step Highly Selective Synthesis and Enhancing Insecticidal Activity and Photo-Self-Degradation of Phenylpyrazole Esterified Derivatives as GABA and nACh Receptor Inhibitors

Liu,

Wu,

et al. 2024

J. Agric. Food Chem.

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In the pursuit of novel insecticides with high activity and a unique mode of action on the GABA receptor, a series of phenylpyrazole esterified derivatives (PEs) were synthesized using an improved Pinner reaction with high selectivity. Lewis acid catalysis was employed in a one-step solvent-thermal method to convert the cyano group of fipronil into an ester unit. FeCl3 was found to exhibit the highest selectivity for PEs synthesis, yielding PEs at 96.4%, with the byproduct being phenylpyrazole amide (PE 0 ) at 2.1%. Initial biological assays indicated superior insecticidal activity of the target compounds against Plutella xylostella and Mythimna separata compared to fipronil. Particularly, the smaller and shorter ester units, PE 3 , PE 5 , and PE 8 , demonstrated 2–2.5 times higher insecticidal activity against P. xylostella than fipronil. The higher activity of ester units compared to amide and acylhydrazone units can be attributed to the enhanced lipid solubility of PEs. Additionally, it may be due to the impact of PEs on the neurotransmitter nACh or the coordination of calcium and chloride ions with the ester’s −CO and −O– bonds, blocking the chloride ion channel. Hydrophobic parameters were confirmed by reversed-phase high-performance liquid chromatography (HPLC), indicating the enhanced lipophilicity conferred by the ester units of PEs. Molecular docking and CoMFA analysis preliminarily validated the strong interactions and structure–activity relationships between PEs and the GABA receptor and nACh receptor in P. xylostella. Furthermore, under simulated natural sunlight, PEs exhibited photodegradation capabilities, transforming back into fipronil parent fragments and enhancing their insecticidal activity. Moreover, PEs displayed excellent fluorescent properties, enabling self-detection of residues. These research findings provide new insights and directions for the development of efficient pesticides, with potential wide applications in the fields of medicine and biosensors.

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Section: Resultsmentioning

confidence: 99%

Design, One-Step Highly Selective Synthesis and Enhancing Insecticidal Activity and Photo-Self-Degradation of Phenylpyrazole Esterified Derivatives as GABA and nACh Receptor Inhibitors

Liu,

Wu,

et al. 2024

J. Agric. Food Chem.

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“…In both insects and mammals, the gamma-aminobutyric acid (GABA) receptor (GABAR) is the primary mediator of rapid inhibitory synaptic signaling in the nervous system. , Insecticides that target GABA-gated chloride channels in insects include polychlorinated cycloalkanes, phenylpyrazoles, arylisoxazolines, , and m -diamides with new binding sites . Phenylpyrazole insecticides, including fipronil, flufiprole, ethiprole, and acetoprole, target the ion channel pores formed by the five TM2 segments .…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Acaricidal/Insecticidal Activities of New Phenylpyrazole Derivatives Comprising an Imide Moiety

Liu,

Ye,

Gao

et al. 2024

J. Agric. Food Chem.

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Using nicofluprole as the lead compound, we designed and synthesized a series of new phenylpyrazole analogues through substituting the methyl group on the nitrogen atom of the amide with an acyl group. Bioassay results showed that compounds A12−A17 with a 1-cyanocyclopropimide group exhibited outstanding insecticidal activity. The LC 50 values for compounds A12−A17 against Tetranychus cinnabarinus ranged from 0.58 to 0.91 mg/L. Compound A15 showed an LC 50 value of 0.29 and 3.10 mg/L against Plutella xylostella and Myzus persicae, respectively. Molecular docking indicated the potential binding interactions of compound A15 with a gamma-aminobutyric acid receptor. Additionally, density functional theory calculations implied that the 1-cyanocyclopropimide structure might be essential for its biological activity. Phenylpyrazole derivatives, containing a 1-cyanocyclopropimide fragment, have the potential for further development as potential insecticides.

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Novel heptafluoroisopropyl N-phenylpyrazole aryl amides containing cyanoalkyl groups: Design, synthesis, insecticidal activity, docking studies and theoretical calculations

Liu,

Bi,

Zhang

et al. 2024

Bioorganic Chemistry

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Structural optimization based on 4,5-dihydropyrazolo[1,5-a]quinazoline scaffold for improved insecticidal activities

Cited by 4 publications

References 49 publications

Design, One-Step Highly Selective Synthesis and Enhancing Insecticidal Activity and Photo-Self-Degradation of Phenylpyrazole Esterified Derivatives as GABA and nACh Receptor Inhibitors

Design, One-Step Highly Selective Synthesis and Enhancing Insecticidal Activity and Photo-Self-Degradation of Phenylpyrazole Esterified Derivatives as GABA and nACh Receptor Inhibitors

Design, Synthesis, and Acaricidal/Insecticidal Activities of New Phenylpyrazole Derivatives Comprising an Imide Moiety

Novel heptafluoroisopropyl N-phenylpyrazole aryl amides containing cyanoalkyl groups: Design, synthesis, insecticidal activity, docking studies and theoretical calculations

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