新型含哌啶结构的脲嘧啶类化合物的设计合成与除草活性研究
收稿日期: 2023-11-21
修回日期: 2024-01-04
网络出版日期: 2024-01-18
基金资助
南宁市科学研究与技术开发计划(20201043); 南宁市创新创业领军人才“邕江计划”创业(2020002-1)
Design, Synthesis and Herbicidal Activity of Novel Uracil Compounds Containing Piperidine Moiety
Received date: 2023-11-21
Revised date: 2024-01-04
Online published: 2024-01-18
Supported by
Nanning Scientific Research and Technology Development Program(20201043); Nanning Innovation and Entrepreneurship Leading Talents “YongJiang Plan” Entrepreneurship Project(2020002-1)
为了寻求新型高效、环境友好的除草化合物, 以2-氟-4-氯苯胺为原料, 依据活性亚结构拼接的方法, 设计合成了26个结构新颖的脲嘧啶类化合物. 其结构经1H NMR、13C NMR、HRMS分析确认. 苗后除草活性测试结果表明, 在浓度为37.5 g/hm2时, 5个化合物对阔叶杂草(百日草、苘麻)的防除效果在90%~100%; 在浓度为9.375 g/hm2时, 仍有2个化合物对阔叶杂草(百日草、苘麻)的防除效果在50%~90%, 且对禾本科杂草(稗草、金色狗尾草)无药害. 分子表面静电势研究表明, 2-氯-N-((1-(环丙烷羰基)哌啶-4-基)甲基)-4-氟-5-(3-甲基-2,6-二氧代-4-三氟甲基-3,6-二氢嘧啶- 1(2H)-基)苯磺酰胺(8i)和Saflufenacil电荷分布相近, 可能在化合物与其靶标受体对接时起重要作用. 分子对接结果表明, 化合物8i与原卟啉原氧化酶存在着多种相互作用, 以上结果为脲嘧啶类化合物的进一步优化奠定了基础.
裴鸿艳 , 叶家麟 , 王锋 , 刘东东 , 余裕奎 , 张静 , 张立新 . 新型含哌啶结构的脲嘧啶类化合物的设计合成与除草活性研究[J]. 有机化学, 2024 , 44(5) : 1592 -1605 . DOI: 10.6023/cjoc202311019
To search the novel, efficient and environmentally friendly herbicide compounds, based on the principle of biologically active factor splicing, 26 uracil compounds with novel structures were designed and synthesized by using 2-fluoro-4-chloroaniline as raw material. The structures were confirmed by 1H NMR, 13C NMR, and HRMS spectra. The results of post-seedling herbicidal activity test showed that the control effect of 5 compounds on broadleaved weeds (Zinnia elegans and Abutilon theophrasti) was 90%~100% at the concentration of 37.5 g/hm2. At a concentration of 9.375 g/hm2, there are still two compounds that have a control effect of 50%~90% on broadleaved weeds (Zinnia elegans and Abutilon theophrasti), and have no harmful effects on gramineous weeds (Echinochloa crus-galli and Setaria glauca). Molecular electrostatic potential showed that 2-chloro-N-((1-(cyclopropanecarbonyl)piperidin-4-yl)methyl)-4-fluoro-5-(3-methyl-2,6- dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzenesulfonamide (8i) and saflufenacil have similar charge distributions, which may play an important role in the docking of the compound with its target receptor. The molecular docking results revealed that compound 8i has various interactions with protoporphyrinogen oxidase. The above results laid the foundation for further optimization of uracil compounds.
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