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Novel phenylpyrimidine derivatives containing a hydrazone moiety protect rice seedlings from injury by metolachlor

文献类型： 外文期刊

作者： Deng, Xile 1 ; Zheng, Wenna 1 ; Jin, Can 1 ; Zhan, Qingcai 1 ; Bai, Lianyang 1 ;

作者机构： 1.Hunan Acad Agr Sci, Hunan Agr Biotechnol Res Inst, Key Lab Biol & Control Weeds, Changsha 410125, Peoples R China

关键词： Metolachlor; Hydrazone; Rice; Herbicide safeners; Glutathione S-transferase

期刊名称：BIOORGANIC CHEMISTRY （ 影响因子：5.275； 五年影响因子：5.252 ）

ISSN： 0045-2068

年卷期： 2021 年 108 卷

页码：

收录情况： SCI

摘要： One strategy for solving the phytotoxicity of herbicides is to apply herbicide safeners that can efficiently alleviate the injuries of agricultural crops caused by herbicides. When metolachlor, a chloroacetamide herbicide, is applied with paddy rice, for example, the mechanisms associated with metolachlor and its residue negatively impact on the growth and yields of rice. To identify novel high-activity herbicide safener candidates for metolachlor, a series of (E)-4-(2-substituted hydrazinyl)-6-chloro-2-phenyl pyrimidines were synthesized and their structures were confirmed using IR (infrared radiation), H-1 NMR, C-13 NMR, and HRMS (high resolution mass spectrometry). The herbicide safener activities were then evaluated via primary tests. Compounds 3i and 3t were found to have the best herbicide activity on plant height. These compounds were then further screened for their activities at lower concentrations and showed better or similar activities compared to the positive control fenclorim, a commercial herbicide safener. The compounds 3i and 3t significantly enhanced glutathione S-transferase (GST) activity related with the herbicide safener activity in both shoots and roots tissues. Moreover, a qPCR (Real-time quantitative polymerase chain reaction) analysis found that the 3i and 3t treatments enhanced the expressions of OsGSTU3, OsGsTU39, and OsGSTF5. Finally, the results of an acute toxicity assessment with zebrafish (Danio rerio) embryos using treatments 3i and 3t indicated they are relatively safe to aquatic organisms.

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