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Synthesis, Insecticidal Activities, and Structure-Activity Relationship of Phenylpyrazole Derivatives Containing a Fluoro-Substituted Benzene Moiety.
- Source :
-
Journal of agricultural and food chemistry [J Agric Food Chem] 2020 Oct 07; Vol. 68 (40), pp. 11282-11289. Date of Electronic Publication: 2020 Sep 25. - Publication Year :
- 2020
-
Abstract
- Fluorinated organic compounds represent a growing and important family of commercial chemicals. Introduction of fluorine into active ingredients has become an effective way to develop modern crop protection products. Given the particular properties of fluorine and high efficiency and selectivity of diamide insecticides, we designed and synthesized 27 anthranilic diamides analogues containing fluoro-sustituted phenylpyrazole. A preliminary bioassay indicated that most target compounds exhibited good biological activity against Mythimna separata and Plutella xylostella . Compound IIIf containing a 2,4,6-trifluoro-substituted benzene ring showed 43% insecticidal activity against M. separata at 0.1 mg L <superscript>-1</superscript> , while the control chlorantraniliprole was 36%. The activity of IIIe against P. xylostella at 10 <superscript>-5</superscript> mg L <superscript>-1</superscript> was 94%, compared with that of the control being 70%. Thus, introduction of fluorine into diamide insecticides was useful for increasing activity. Insect electrophysiology studies showed that the calcium concentration in the nerve cells of third M. separata larvae was elevated by IIIf , which further confirmed that ryanodine receptor (RyR) was its potential target.
- Subjects :
- Animals
Benzene pharmacology
Calcium Channel Blockers chemistry
Calcium Channel Blockers pharmacology
Insect Proteins antagonists & inhibitors
Insect Proteins chemistry
Insect Proteins metabolism
Insecticides chemistry
Larva drug effects
Larva growth & development
Larva metabolism
Molecular Structure
Moths drug effects
Moths growth & development
Moths metabolism
Pyrazoles pharmacology
Ryanodine Receptor Calcium Release Channel chemistry
Ryanodine Receptor Calcium Release Channel metabolism
Structure-Activity Relationship
Benzene chemistry
Insecticides chemical synthesis
Insecticides pharmacology
Pyrazoles chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1520-5118
- Volume :
- 68
- Issue :
- 40
- Database :
- MEDLINE
- Journal :
- Journal of agricultural and food chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 32926621
- Full Text :
- https://doi.org/10.1021/acs.jafc.9b08090