Synthesis, Physicochemical Properties, and Biological Activities of 4-( S -Methyl- N -(2,2,2-Trifluoroacetyl)Sulfilimidoyl) Anthranilic Diamide

• Published in: Molecules (Basel, Switzerland) Vol. 24; no. 19; p. 3451
• Main Authors: Lim, Hwan Jung, Lee, Won Hyung, Park, Seong Jun
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 23.09.2019; MDPI
• Subjects: Acids; Animals; anthranilic diamide; Antiviral Agents - chemical synthesis; Antiviral Agents - pharmacology; Biological properties; Chromatography; Chromatography, Thin Layer; Communication; Diamide - chemistry; insecticide; Insecticides; Insecticides - chemical synthesis; Insecticides - pharmacology; Isoxazoles - chemistry; Organosulfur compounds; Permeability; Physical properties; Physicochemical properties; Plant protection; Potassium; Pyrazole; Spodoptera - drug effects; Structure-Activity Relationship; sulfilimine; sulfoximine; sulfoximine; insecticide; anthranilic diamide; sulfilimine
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules24193451

Novel anthranilic diamides with sulfilimidoyl and sulfoximidoyl functionalities were successfully prepared. Among newly-prepared organosulfur compounds, 3-bromo-1-(3-chloropyridin-2-yl)- -(2-methyl-6-(methylcarbamoyl)-4-(methylthio)phenyl)-1 -pyrazole-5-carboxamide and ( , )-3-bromo-1-(3-chloropyridin-2-yl)- -(2-methyl-4-(S-methyl- -(2,2,2-trifluoroacetyl)sulfinimidoyl)-6-(methylcarbamoyl)phenyl)-1 -pyrazole-5-carboxamide showed good levels of efficacy and a strong correlation between insecticidal activities and physical properties, respectively. In particular, available data indicated that the -trifluoroacetyl sulfilimine moiety could be an appealing structural scaffold for the discovery of a new crop-protecting agent.