PUBLICATION
Design, Synthesis, and Biological Activities of Novel Phenylpyrazole Derivatives Containing a Trifluoromethylselenyl Moiety
- Authors
- Dong, L., Chang, W., Yang, W., Xu, Z., Cheng, J., Shao, X., Xu, X., Li, Z.
- ID
- ZDB-PUB-230721-42
- Date
- 2023
- Source
- Journal of Agricultural and Food Chemistry 71(30): 11396-11403 (Journal)
- Registered Authors
- Keywords
- insecticidal activity, molecular docking, phenylpyrazole, toxicity on zebrafish embryos, trifluoromethylselenyl
- MeSH Terms
-
- Animals
- Insecticides*/chemistry
- Moths*
- Structure-Activity Relationship
- Zebrafish
- PubMed
- 37471065 Full text @ J. Agric. Food Chem.
Citation
Dong, L., Chang, W., Yang, W., Xu, Z., Cheng, J., Shao, X., Xu, X., Li, Z. (2023) Design, Synthesis, and Biological Activities of Novel Phenylpyrazole Derivatives Containing a Trifluoromethylselenyl Moiety. Journal of Agricultural and Food Chemistry. 71(30):11396-11403.
Abstract
Phenylpyrazole insecticides are widely used for crop protection and public sanitation by blocking gamma-aminobutyric acid (GABA)-gated chloride channels and glutamate-gated chloride (GluCl) channels. Herein, 36 novel phenylpyrazole derivatives containing a trifluoromethylselenyl moiety were designed and synthesized based on the strategy of introducing a selenium element. All derivative structures were characterized by nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS). The insecticidal activity results indicated that some derivatives had good insecticidal activities against Aedes albopictus (A. albopictus) and Plutella xylostella (P. xylostella). The larvicidal activity against mosquitos of compounds 5, 5a, 5k, and 5l at 0.5 mg/L was 60-80%. At a concentration of 500 mg/L, compounds 5, 5a, 5h, 5k, 5l, 5r, 6, 6j, 6k, and 7 showed a 70-100% mortality against P. xylostella. Among them, derivatives 5 and 6 had a better insecticidal effect with mortality rates of 87 and 93% at 50 mg/L, respectively. It was summarized that the different binding poses of fipronil and compounds 5 and 6 in the Musca domestica (M. domestica) GABARs might lead to the disparity in bioactivity from docking studies. Toxicity tests on zebrafish suggested that compound 6 may be slightly less toxic to the embryos than fipronil on hatching rate.
Genes / Markers
Expression
Phenotype
Mutations / Transgenics
Human Disease / Model
Sequence Targeting Reagents
Fish
Orthology
Engineered Foreign Genes
Mapping