Novel Insecticidal Benzo[4,5]imidazo[1,2‐b]pyrazole Derivatives Identified through Ring‐Closure Scaffold Hopping on Fipronil DOI Open Access
Cong Zhou, Guanglong Li, Sihui Wang

et al.

Chemistry & Biodiversity, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 27, 2024

Abstract A series of innovative benzo[4,5]imidazo[1,2‐ b ]pyrazole scaffold containing compounds were rationally designed through a ring‐closure hopping strategy and synthetized with an intermediate derivatization approach. Physicochemical properties analysis indicated the potential pesticide‐likeness target compounds. The optimal compound A14 showed relatively good insecticidal activity against P. xylostella , LC 50 value 37.58 mg/L, demonstrated lower acute fish toxicity compared to fipronil. Docking binding mode that bound GABAR H‐bond between amide group residue 6’Thr. differences in modes fipronil may be key factor for reduced activities. elucidated SAR profile lay foundation further structural optimization derivatives.

Language: Английский

Discovery of Novel Neonicotinoids with Conjugated Diene Enabled by Cascade Allylation/Isomerization Synthetic Methodology DOI
Dongxu Zhang, Cong Zhou, Suzhen Qi

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 22, 2025

As one of the most significant insecticides, neonicotinoids have played a pivotal role in crop protection and public sanitation. However, high resistance bee toxicity neonicotinoid insecticides attracted considerable attention. Herein, series compounds with conjugated diene moieties were synthesized through cascade allylation/isomerization reaction. Most target exhibited excellent insecticidal activities against Aphis craccivora, some good Mythimna separata. In particular, compound A15 showed outstanding activity A. craccivora (LC50 = 0.15 mg/L), which was superior to that imidacloprid 0.36 mg/L). addition, this candidate minimal cross-resistance imidacloprid. The acute contact tests on Apis mellifera suggested 10 times less toxic than Electrophysiological experiments molecular docking studies indicated exerted its effects by interfering nicotinic acetylcholine receptors. This work identifies novel potential for further development.

Language: Английский

Citations

0
Synthesis of Amides via the Amination of Aldehydes with Hydroxylamines Promoted by TBAF·3H2O DOI
Huaiyuan Zhang, Nuo Xu,

Botao Su

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 7579 - 7590

Published: May 23, 2024

A metal-free, mild, and efficient method for the synthesis of amides has been developed from amination aldehydes with hydroxylamines promoted by TBAF·3H

Language: Английский

Citations

1
Novel Insecticidal Benzo[4,5]imidazo[1,2‐b]pyrazole Derivatives Identified through Ring‐Closure Scaffold Hopping on Fipronil DOI Open Access
Cong Zhou, Guanglong Li, Sihui Wang

et al.

Chemistry & Biodiversity, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 27, 2024

Abstract A series of innovative benzo[4,5]imidazo[1,2‐ b ]pyrazole scaffold containing compounds were rationally designed through a ring‐closure hopping strategy and synthetized with an intermediate derivatization approach. Physicochemical properties analysis indicated the potential pesticide‐likeness target compounds. The optimal compound A14 showed relatively good insecticidal activity against P. xylostella , LC 50 value 37.58 mg/L, demonstrated lower acute fish toxicity compared to fipronil. Docking binding mode that bound GABAR H‐bond between amide group residue 6’Thr. differences in modes fipronil may be key factor for reduced activities. elucidated SAR profile lay foundation further structural optimization derivatives.

Language: Английский

Citations

0