Synthesis, herbicidal activity and soil degradation of novel 5‐substituted sulfonylureas as AHAS inhibitors

Abstract

BACKGROUND Chlorsulfuron, metsulfuron‐methyl and ethametsulfuron can damage sensitive crops in rotation pattern as a result of their long persistence in soil. To explore novel sulfonylurea (SU) herbicides with favorable soil degradation rates, four series of SUs were synthesized through a structure‐based drug design (SBDD) strategy. RESULTS The target compounds, especially Ia, Id and Ie, exhibited prospective herbicidal activity against dicotyledon oil seed rape (Brassica campestris), amaranth (Amaranthus retroflexus), monocotyledon barnyard grass (Echinochloa crusgalli) and crab grass (Digitaria sanguinalis) at a concentration of 15 a.i. g ha−1. Additionally, Ia, Id and Ig displayed excellent inhibitory effects against AtAHAS, with Kapp i values of 59.1, 34.5 and 71.8 μm, respectively, which were much lower than that of chlorsulfuron at 149.4 μm. The π‐π stack and H‐bonds between the Ia conformation and AtAHAS in the molecular docking results confirmed the series of compounds to be conventional AHAS inhibitors. In alkaline soil (pH = 8.46), compounds Ia–Ig revealed various degrees of acceleration in the degradation rate compared with chlorsulfuron. Besides, compound Ia showed considerable wheat and corn safety under postemergence at the concentration of 30, 60 and even 120 a.i. g ha−1. CONCLUSION Overall, based on the synthetic procedure, herbicidal activity, soil degradation and crop safety, the Ia sulfonylureas series were chosen to be investigated as prospective AHAS inhibitors. The 5‐dimethylamino group on SUs accelerated the degradation rate at different levels in alkaline soils which seems to be controllable in conventional cropping systems in their further application. © 2022 Society of Chemical Industry.

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“…Synthetic pesticides have been investigated for their persistence in the environment (Zhou et al 2022 ; Merlo-Reyes et al 2024 ), as well as the metabolites or transformation products of their active principles during the degradation process (Vargas-Pérez et al 2020 ; López-Ruiz et al 2020 ). Despite the growing expansion of biopesticides, studies of their degradation in the environment are limited (López-Serna et al 2016 ; Huang et al 2022 ).…”

A pH‐responsive MOF‐functionalized hollow mesoporous silica controlled herbicide delivery system exhibits enhanced activity against ACCase‐herbicide‐resistant weeds

“…4 Barnyard grasses grow especially well in water-logged soil and have invaded the 'territory' of rice (Oryza sativa) plants. 5 one of the major food crops for over half of the world's population. 6 Barnyard grasses exhibit typical adaptive behavior to aggressively compete with rice plants in agricultural systems.…”

“…They are widely distributed from temperate to tropical regions, and are classified as the most serious weed for 36 different crop plants in 61 countries 4 . Barnyard grasses grow especially well in water‐logged soil and have invaded the ‘territory’ of rice ( Oryza sativa ) plants 5 . one of the major food crops for over half of the world's population 6 .…”