Design, Synthesis, and Herbicidal Activity of Thioether Containing 1,2,4-Triazole Schiff Bases as Transketolase Inhibitors

Abstract

Transketolase (TK) represents a potential target for novel herbicide development. To discover novel TK inhibitors with potency against resistant weeds, 36 thioether compounds containing 1,2,4-triazole Schiff bases were designed and synthesized for herbicidal activity evaluation. The results demonstrated that compounds 5av and 5aw provided excellent weed control with inhibition of over 90% against the tested weeds, even at concentrations as low as 100 mg/L in vitro. In addition, compounds 5av and 5aw exhibited higher postemergence herbicidal activity than all of the positive controls against the tested weeds at 50−90 g [active ingredient (ai)]/ha in a greenhouse, while being safe for crops of maize and wheat at 90 g (ai)/ha. Fluorescent binding experiments of At TK indicated that compounds 5av and 5aw had strong TK inhibitory activity and could tightly bind with the enzyme At TK. Also, molecular docking analyses revealed that the structures of compounds 5av and 5aw were suitable for TK inhibitory activity. Taken together, these results suggested that compounds 5av and 5aw were promising herbicide candidates for weed control in wheat and maize fields targeting TK.

Design, Synthesis, and Herbicidal Activity of Naphthalimide–Aroyl Hybrids as Potent Transketolase Inhibitors

“…Instruments and Reagents. 1 H and 13 C nuclear magnetic resonance (NMR) spectra were taken on a Varian 400 spectrometer using tetramethylsilane as an internal reference (in CDCl 3 or DMSOd 6 ). ESI-MS was performed using an Agilent G6300 ion Trap mass spectrometer, and signals were recorded in m/z.…”

“…Weeds directly competed with crops for nutrients, moisture, and light, which can cause over 80% crop yield loss. 1,2 A lot of herbicides have been widely used in agricultural production for weed control, which greatly increased the crop production. 1,3,4 Target-based drug design (TBDD) has attracted great attention because of its numerous advantages, including high selectivity, high efficiency, and safety for nontarget organisms.…”

“…Previously, we have developed a new range of TK-inhibitors, such as 1,2,4-triazole Schiff bases 5aw and 5av. 1 Early findings suggested that the TK inhibitor formed a stable complex with TK protein and exerted their TK inhibitory effects by stronger interactions with the key amino acids in the active site. 1,4 Contemporary drug molecular design has entered the era of targeted and precise design.…”

“…1 Early findings suggested that the TK inhibitor formed a stable complex with TK protein and exerted their TK inhibitory effects by stronger interactions with the key amino acids in the active site. 1,4 Contemporary drug molecular design has entered the era of targeted and precise design. Systematic elucidation of the three-dimensional structure and mode of action (MOA) of molecular target is the key to new pesticides discovery.…”

Synthesis, antifungal activity, and DFT calculation study of novel 1-acyl-5- amino-1,2,4-triazole-thioether derivatives containing natural gem-dimethylcyclopropane ring structure

“…Heterocyclic compounds, particularly those containing nitrogen, play important roles in biologically active compounds. [11] 1,2,4-Triazoles, an important class of ve-membered heterocyclic compounds containing nitrogen, [12] were demonstrated to present versatile biological activities, such as antifungal, [13][14] antiviral, [15] herbicidal, [16] insecticidal, [17] DPP-4 inhibitory, [18] and anticancer [19] activities. Besides, the thioether linkage in bioactive molecules was thought to improve drug-likeness by lowering lipophilicity and acting as a favorable Hbond acceptor.…”