Sulfonamide modified chitosan oligosaccharide with high nematicidal activity against Meloidogyne incognita

Int J Biol Macromol. 2024 May 6;269(Pt 2):132131. doi: 10.1016/j.ijbiomac.2024.132131. Online ahead of print.

Abstract

Chitosan oligosaccharide (COS) modification is a feasible way to develop novel green nematicides. This study involved the synthesis of various COS sulfonamide derivatives via hydroxylated protection and deprotection, which were then characterized using NMR, FTIR, MS, elemental analysis, XRD, and TG/DTG. In vitro experiments found that COS-alkyl sulfonamide derivatives (S6 and S11-S13) exhibited high mortality (>98 % at 1 mg/mL) against Meloidogyne incognita second-instar larvaes (J2s) among the derivatives. S6 can cause vacuole-like structures in the middle and tail regions of the nematode body and effectively inhibit egg hatching. In vivo tests have found that S6 has well control effects and low plant toxicity. Additionally, the structure-activity studies revealed that S6 with a high degree of substitution, a low molecular weight, and a sulfonyl bond on the amino group of the COS backbone exhibited increased nematicidal activity. The sulfonamide group is a potential active group for developing COS-based nematicides.

Keywords: Chitosan oligosaccharide (COS); Meloidogyne incognita; Modification; Nematicide; Root-knot nematode; Sulfonamide groups.