Design, Synthesis, Insecticidal Activity, and SAR of Aryl Isoxazoline Derivatives Containing Pyrazole-5-carboxamide Motif

It is important to develop new insecticides with a new mode of action because of increasing pesticide resistance. In this study, a series of novel aryl isoxazoline derivatives containing the pyrazole-5-carboxamide motif were designed and synthesized. Their structures were confirmed by 1H NMR, 13C NM...

Full description

Saved in:
Bibliographic Details
Published inJournal of agricultural and food chemistry Vol. 71; no. 40; pp. 14458 - 14470
Main Authors Zhong, Liang-Kun, Sun, Xin-Peng, Han, Liang, Tan, Cheng-Xia, Weng, Jian-Quan, Xu, Tian-Ming, Shi, Jian-Jun, Liu, Xing-Hai
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 11.10.2023
Amer Chemical Soc
Subjects
Agricultural and Environmental Chemistry
Agriculture
Agriculture, Multidisciplinary
Chemistry
Chemistry, Applied
Food Science & Technology
Life Sciences & Biomedicine
Physical Sciences
Science & Technology
synthesis
GABA
aryl isoxazoline compounds
molecular docking
SAR
FLURALANER
NEMATOCIDAL ACTIVITY
GATED CHLORIDE CHANNELS
CARBOXAMIDE
Online AccessGet full text

Cover

More Information
Summary:It is important to develop new insecticides with a new mode of action because of increasing pesticide resistance. In this study, a series of novel aryl isoxazoline derivatives containing the pyrazole-5-carboxamide motif were designed and synthesized. Their structures were confirmed by 1H NMR, 13C NMR, and HRMS. Bioassays indicated that the 24 compounds synthesized possessed excellent insecticidal activity against Mythimna separate and no activity against Aphis craccivora and Tetranychus cinnabarinus. Among these aryl isoxazoline derivatives, 3-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydrozol-3-yl)-N-(4-fluorophenyl)-1-methyl-1H-pyrazole-5-carboxamide (IA-8) had the best insecticidal activity against M. separate, which is comparable with the positive control fluralaner. The molecular docking results of compound IA-8 and fluralaner with the GABA model demonstrated the same docking mode between compound IA-8 and positive control fluralaner in the active site of GABA. Molecular structure comparisons and ADMET analysis can potentially be used to design more active compounds. The structure–activity relationships are also discussed. This work provided an excellent insecticide for further optimization.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0021-8561
1520-5118
DOI:10.1021/acs.jafc.3c01608