Design, Synthesis, and Herbicidal Activity Study of Novel Pyrazole-Carboxamides as Potential Transketolase Inhibitors

IF 5.7 1区 农林科学 Q1 AGRICULTURE, MULTIDISCIPLINARY
Chengkun Li, Junmin Wang, Haijiao Dong, Dongchen Yang, Peng Li, Shuang Cao, Chao Li, Zexiu An, Jinlin Zhang, Yan-En Wang
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Abstract

Transketolase (TKL; EC 2.2.1.1) has been identified as a potential new herbicide target. In order to discover highly herbicidal active compounds targeting TKL and improve their structural diversity for lead compounds, a series of pyrazole-carboxamides 7a7v were designed and synthesized through structural optimization for pyrazole-containing phenoxy amide compound 4u. Among the synthesized compounds, compound 7r possessed excellent herbicidal efficacy against Digitaria sanguinalis (Ds) and Amaranthus retroflexus (Ar) by the small cup method (the inhibition about 95%, 100 mg/L) and the foliar spray method (the inhibition over 90%, 150 g ai/ha) in a greenhouse, which were superior to that of the positive control nicosulfuron. More significantly, compound 7r displayed good crop selectivity toward both maize and wheat even at 375 g of ai/ha. The studies on mode of action (MOA) of high herbicidal active compounds, including the enzyme inhibition activity, fluorescent quenching experiments, and molecular docking analysis between Setaria viridis (Sv)TKL and ligand, suggested that compound 7r acts as a typical TKL inhibitor, and the benzothiazole ring is an important motif for SvTKL inhibition activity. Above all, compound 7r could be a potential candidate for the development of herbicides with new MOA for weed control in maize and wheat field.

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来源期刊
Journal of Agricultural and Food Chemistry
Journal of Agricultural and Food Chemistry 农林科学-农业综合
CiteScore
9.90
自引率
8.20%
发文量
1375
审稿时长
2.3 months
期刊介绍: The Journal of Agricultural and Food Chemistry publishes high-quality, cutting edge original research representing complete studies and research advances dealing with the chemistry and biochemistry of agriculture and food. The Journal also encourages papers with chemistry and/or biochemistry as a major component combined with biological/sensory/nutritional/toxicological evaluation related to agriculture and/or food.
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