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

Application of Difluoromethyl Isosteres in the Design of Pesticide Active Molecules DOI

Wanjie Zhang,

Pengxiang Guo,

Yannian Zhang

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 21, 2024

Difluoromethyl (CF

Language: Английский

Citations

0
From Proline to Chlorantraniliprole Mimics: Computer-Aided Design, Simple Preparation, and Excellent Insecticidal Profiles DOI

Shu-Zhen Xiang,

K Liu,

Jinjing Wang

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 4, 2024

Chlorantraniliprole (CHL), a favored agricultural insecticide, is renowned for its high efficiency and broad-spectrum effectiveness against lepidoptera insects. However, the urgency new insecticide development underscored by intricate multistep preparation process modest overall yields of CHL, along with escalating challenge insect resistance. In response, we have crafted CHL mimics from proline employing computer-aided drug design. Molecular docking analysis CHL's interactions ryanodine receptor (RyR) revealed that nitrogen atom within pyrazole moiety does not engage in pivotal interactions. Its removal may abolish bioactivity entirely but could substantially simplify synthetic process, thereby enhancing economy. This revelation prompted exclusion subsequent formation pyrrole ring, enabling meticulous design pathways characterized cost-effective precursors, streamlined synthesis, avoidance toxic reagents, minimal instrumentation, pursuit innovative RyR modulators. Among these modulators,

Language: Английский

Citations

0
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