Synthesis and Insecticidal Activity of N-Substituted (1,3-Thiazole)alkyl Sulfoximine Derivatives

Abstract

The N-substituted alkyl sulfoximine derivatives are a new chemical family of neonicotinoid insecticides. We have designed and synthesized 10 (1,3-thiazole)alkyl sulfoximine derivatives. All compounds were identified by (1)H and (13)C nuclear magnetic resonance (NMR), IR, and elemental analyses. Preliminary bioassays indicated that some title compounds exhibited good insecticidal activities at 10 mg/L against Myzus persicae . The relationship between structure and biological activity was also discussed.

Overall status of neonicotinoid insecticides in China: Production, application and innovation

“…11) had the highest activity, which was comparable to Sulfoxaflor among these analogues. 16) (Fig. 12).…”

Synthesis, Crystal Structure and Insecticidal Activity of the Optical Active Neonicotinoid Analogues

“…In addition, the products were separated out from the solution and collected by washing with ethanol (10 mL×3). All the structures were well characterized by IR, 1 H NMR and elemental analysis.…”

“…1 Since imidacloprid 2 as the first generation NNSs was introduced to the market, many new generation NNSs, such as dinotefuran 3 are now on the market with their own prominence (Scheme 1). However, during last decade, significant increases in resistance and cross-resistance were observed in a range of species after frequent applications of NNSs.…”

Design, synthesis, crystal structure, bioactivity, and molecular docking studies of novel sulfonylamidine-derived neonicotinoid analogs

“…Modification of the structures of existing neonicotinoids can be an effective tactic to combat resistance. For example, sulfoximines have proved to be useful structural motifs in active, non-cross-resistant insecticides, and may be involved in recognition and interactions with the insect target (Loso et al, 2008;Zhu et al, 2010;Yu et al, 2008;Zhu et al, 2011). As shown in Fig.…”