Design, Synthesis and Biological Activity Screening of Novel Amide Derivatives Containing Aromatic Thioether Group

Abstract

A series of amide derivatives containing aromatic sulfide and sulfone groups synthesized in our previous work displayed excellent nematocidal activity at 200 μg/mL. In order to explore the effect of structural modification of the amide bridge on biological activity in a more delicate way, two series of novel target compounds were designed and synthesized by adopting amide group flipping and introducing N-sulfonyl substituted amide bonds. The bioassays indicated that the structural modification of the amide bridge had important effects on their nematocidal and fungicidal activities, which the introduction of the N-sulfonyl substituent on the amide group was favorable to improving the nematocidal activity in comparison with compounds I. The molecular docking revealed that directly attaching the carbonyl or sulfonyl groups in the amide bridge to the aromatic rings was advantageous to the nematocidal activity.

Studies on the novel pyridine sulfide containing SDH based heterocyclic amide fungicide

“…2.2 Synthesis of the target compounds 2.2.1 General synthetic procedure for target compounds I-1-I-10 N-(2-((3-Chloro-5-(trifluoromethyl)pyridin-2-yl)thio)ethyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide was synthesized according to the literature procedure. 24,25 A mixture of 3-chloro-5-(trifluoromethyl)pyridine-2-thiol (1.1 mmol), potassium carbonate (1.3 mmol) in dimethylformamide (DMF) (5 mL) was heated to 80°C and stirred for 10 min, followed by addition of N-(2-chloroethyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide (1.0 mmol). Studies on the novel fungicidal pyridine sulfides www.soci.org…”

“…24 Subsequently, the nematicidal and fungicidal activities were measured in turn to summarize the structure and activity relationships (SARs), in which compound h-IV was discovered to have a good nematicidal activity. 24 Surprisingly, the compound I-1 with excellent fungicidal activity was found through the preliminary biological activity screening (Fig. 3).…”

Recent achievements on the agricultural applications of thioether derivatives: A 2010–2020 decade in review

“…and B. cinerea t at 50 μg/mL than those of Pyrimethanil. In addition, a series of novel thioether derivatives containing an amide group were prepared by Hua et al [56], and bioassays indicated that the target compounds had certain activities against G. zeae, R. solani, C. capsica, P. melongenae, B. cinerea, P. piricola, A. kikuchiana, and C. circumscissa. Among the tested compounds, compound 45 (Figure 9) displayed better fungicidal activity against C. capsici (81.7%) than that of Fluopyram.…”

Synthesis and biological activity of amide derivatives derived from natural product Waltherione F

“…1). [15] In this project, combined with the fungicidal amide lead compound h-I-9 discovered in our previous work and fungicidal piperazine compounds P-1 and P-2 reported in literatures, [16][17][18][19][20][21] the amide derivatives containing 4-quinolone and piperazine substructures were designed, prepared and screened for their biological activity (Fig. 2).…”