Design, Synthesis, and Antifungal Activity of Sulfoximine Derivatives Containing Nitroguanidine Moieties

Abstract

To discover novel pesticide candidates, a series of sulfoximine derivatives were designed and synthesized via the oxidation coupling reaction of sulfides and N-alkyl nitroguanidines. The compounds were evaluated for their antifungal activity against six phytopathogenic fungi. Most of them exhibited a broad spectrum of fungicidal activity in vitro. Compound 8IV-b displayed good fungicidal activity against

Novel Sulfoximine Derivatives Containing Cyanoguanidine and Nitroguanidine Moieties: Design, Synthesis, and Bioactivities

“…As shown in Figure , the target compounds were synthesized by using benzyl chlorides as the starting materials. The key intermediates 3 , 6 , 7 , and title compounds were prepared based on the literature procedures. − …”

“…In this regard, nitroguanidine, which allows for the construction of diverse molecules, bears multiple hydrogen bond acceptors or donors and always works as a skeleton in active agents, is more beneficial for the building of a new scaffold of sulfoximine. We designed and synthesized a series of sulfoximine derivatives containing nitroguanidine moiety (VII) . The bioactivity screening showed that those compounds exhibited lower insecticidal activity against M.…”

Design, synthesis, and antifungal activities of novel sulfoximine derivatives for plant protection

“…As depicted in Schemes 1 and 2, the title compounds were prepared via four steps that started from benzyl chloride as the raw material and involved three intermediates, 2 , 4 , and 5 . The key intermediates were synthesized according to the literature procedure 33‐36 …”

“…The key intermediates were synthesized according to the literature procedure. [33][34][35][36] 2.2.1 General synthetic procedure for intermediates 2 To a solution of alkyl halide 1 (0.1 mol) in ethanol at 0 °C was added sodium methyl mercaptide 2 (0.15 mol, 20% water solution), and then the mixture was stirred at room temperature for 3 h. The resulting mixture was poured into 100 mL of water, extracted with ethyl acetate (3 × 100 mL), washed with saturated brine (3 × 50 mL), dried over anhydrous Na 2 SO 4 , and concentrated in vacuo to provide compound 2.…”