The synthesis and crystal structure of ethyl (E)-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-5-((2-methoxybenzylidene)amino)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C22H15N3Cl2F6O4S

Chen, Lianqing; Zhang, Long; Tang, Chenglong; Wu, Zhongda

doi:10.1515/ncrs-2019-0898

Cited by 1 publication

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“…After the reaction was finished, it was cooled naturally to room temperature and the excess solvent was removed by a rotary evaporator to obtain brown oil. And 50 mL of ethyl acetate and 100 mL of distilled water were added for extraction, MgSO 4 was used to dry the organic phase, and then the filtrate was adsorbed on activated silica gel and dried samples were made by rotary evaporation . The crude product was obtained by column chromatography on silica gel using ethyl V ethyl acetate /V petroleum ether (1:4–8) as eluent and dried under vacuum to obtain the purified products PE 1 – PE 10 and PE 0 .…”

Section: Materials and Methodsmentioning

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: Materials and Methodsmentioning

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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show abstract

The synthesis and crystal structure of ethyl (E)-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-5-((2-methoxybenzylidene)amino)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C₂₂H₁₅N₃Cl₂F₆O₄S

Abstract: C22H15N3Cl2F6O4S, monoclinic, P1̄ (no. 14), a = 13.6099(10) Å, b = 12.0571(9) Å, c = 16.2351(13) Å, α = 90°, β = 112.714(2)°, γ = 90°, V = 1146.7(7) Å3, Z = 4, Rgt(F) = 0.0419, wRref(F2) = 0.1087, T = 173 K.

Cited by 1 publication

References 5 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

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