Fabrication of Amphiphilic Carfentrazone-Glucosamine Prodrug Self-Assembly for Enhancement of Herbicidal Efficiency and Environment Safety

Abstract

Herbicides play a pivotal role in safeguarding global food security by mitigating weed infestations that threaten crop yield and quality. However, the inherent limitations of herbicides, including poor aqueous solubility and dispersibility, restricted systemic translocation, and potential toxicity to nontarget organisms, constrain their practical application in agricultural systems. Herein, an amphiphilic amide-linked carfentrazone-glucosamine prodrug (CGP) was constructed by covalently conjugating the poorly water-soluble contact herbicide carfentrazone (CAR) with hydrophilic glucosamine and subsequently self-assembled into nanoparticles (CGP NPs) in water for enhancement of efficacy and safety of CAR. The results showed that the obtained CGP NPs exhibited small average size, excellent dispersibility, and robust stability under diverse conditions. Molecular docking and in planta experiments demonstrated that glucosamine incorporation in prodrug enhanced affinity toward plant monosaccharide transporters, enabling bidirectional translocation of CAR through both phloem and xylem, thereby achieving superior herbicidal efficacy compared with carfentrazone-ethyl. Furthermore, CGP NPs exerted negligible effects on soil enzyme and microbial diversity while attenuating CAR-induced phytotoxicity to wheat seedlings, genotoxicity to Vicia faba root tip cells, and acute toxicity to zebrafish. Therefore, the glucosamine-based prodrug self-assembly strategy effectively addresses the limitations of CAR and represents a promising avenue for improving herbicide efficiency while reducing associated environmental risks.