分会

第五十三分会：农业化学与农产品

摘要

新型吡咯类杀菌剂合成设计及其3D-QSAR研究 徐洪亮1，苏静2，侯晨忻3，马腾飞4，朱晓磊5，王子时1,* 1黑龙江大学，黑龙江省哈尔滨市，150080 2华中师范大学，湖北省武汉市，430070 *Email: Wangzishi7@hlju.edu.cn 为寻找具有更高生物活性、更环保的新型绿色农药，本文基于杀菌剂氟咯菌腈设计并合成了21个苯基吡咯类化合物，其中8个化合物的结构未见文献报道，15个化合物的杀菌活性未被文献报道。 目标化合物以取代的苯甲醛为原料进行合成，并在吡咯环上引入甲基基团，其目的是探究其杀菌活性的变化。本文采用1H NMR、FTIR、单晶X-射线衍射、元素分析和熔点测定等测试手段对目标化合物及其中间体的结构进行了表征与确认，并通过挥发法培养得到10个苯基吡咯类化合物的单晶结构。生物活性测试结果显示：在1 mg/L和10 mg/L浓度条件下，该类化合物对Fusarium moniliforme、Rhizoctonia solani、Pyricularia oryzae、Fusarium oxysporum表现出较好的抑菌活性，体现了广谱性的杀菌效果，而氮位甲基取代的目标化合物则只对Rhizoctonia solani表现出较好的抑菌活性，这正由于在吡咯环上引入了甲基基团导致该类化合物的生物活性出现明显变化，从而表现出专一性的特点。基于上述情况对所合成的21个化合物的杀菌活性进行3D-QSAR研究。将Rhizoctonia solani得到的IC50值转化成pIC50值进行数据集的测试。采用比较分子力场分析 (CoMFA)方法，建立了三维定量构效关系CoMFA模型 (q2＝0.503，r2＝0.974)。CoMFA模型的立体场、静电场、三维等势图非常直观地解释了结构与杀菌活性的关系，展现了较好的预测能力，也为后续该系列化合物的进一步优化提供了理论支持。 Table. 1 Summary of CoMFA analysis q2 N r2 S F 0.503 5 0.974 0.219 81.345 Fig. 1 Overlap of all the 20 target compounds 关键词：吡咯类化合物；杀菌剂；氮位取代；生物活性；3D-QSAR 参考文献 [1] 王子时, 叶汉韬, 肖丹, 马东升, 高金胜, 于颖慧, 侯广峰, 闫鹏飞. Chin. J. Org. Chem. 2014, 34: 2057. [2] 王子时, 路运才, 吴鹏冲, 李丽, 高金胜. 一种氮位取代苯基吡咯类化合物及其在植物杀菌中的用途[P]. 申请号: 202010335383.3, 黑龙江大学, 2020-04-25. [3] Zhang, J.; Wang, Z. S.; Xing, Y.; Hou, C. X.; Zhou, Q.; Sun, Y.; Sun, Y.; Xu, H. L.; Gao, J. S. Spectrosc. Let. 2020, 53(5): 360-371. Design, Synthesis and 3D-QSAR Research of New Pyrrole Fungicides HongLiang Xu 1, Jing Su 2, ChenXin Hou 3, TengFei Ma 4, XiaoLei Zhu 5, ZiShi Wang 1,* 1School of Modern Agriculture and Ecological Environment, University of HeiLongJiang, HeiLongJiang Province, Harbin City, 150080 2Central China Normal University, HuBei Province, WuHan City, 430070 *Email: Wangzishi7@hlju.edu.cn In order to find new potential fungicide candidates with higher biological activity and environmentally friendly properties, we designed and synthesized 21 new pyrrole compounds based on the structures of fludioxonil. And a methyl group was introduced into the pyrrole ring to explore the change of its bactericidal activity. All the structures of target products and their intermediates were characterized and confirmed by 1H NMR, FTIR, single crystal X -Ray diffraction, elemental analysis and melting point determination. The single crystals of 10 final products were obtained by volatilizing at room temperature. The biological activity test results show that under the conditions of 1 mg/L and 10 mg/L, these compounds have good antibacterial activity against Fusarium moniliforme, Rhizoctonia solani, Pyricularia oryzae, and Fusarium oxysporum, which indicate a broad-spectrum bactericidal effect. However, the target compounds substituted with methyl at the nitrogen position only show good antibacterial activity against Rhizoctonia solani, because the introduction of a methyl group on the pyrrole ring leads to significant changes in the biological activity of these compounds, thus showing the characteristics of specificity. Comparative molecular field analysis (CoMFA) method was applied to the study on the three-dimensional quantitative structure activity relationship (3D-QSAR) of target compounds. A CoMFA model (q2=0.503, r2=0.974) of three-dimensional quantitative structure-activity relationship was established. The three-dimensional field, electrostatic field, and three-dimensional equipotential diagram of the CoMFA model intuitively explain the relationship between structure and bactericidal activity, show a good prediction ability, and also provide theoretical support for the further optimization of this series of compounds. Keywords: Pyrrole compounds; Fungicide; Nitrogen substitution; biological activity; 3D-QSAR References [1] 王子时, 叶汉韬, 肖丹, 马东升, 高金胜, 于颖慧, 侯广峰, 闫鹏飞. Chin. J. Org. Chem. 2014, 34: 2057. [2] 王子时, 路运才, 吴鹏冲, 李丽, 高金胜. 一种氮位取代苯基吡咯类化合物及其在植物杀菌中的用途[P]. 申请号：202010335383.3, 黑龙江大学, 2020-04-25. [3] Zhang, J.; Wang, Z. S.; Xing, Y.; Hou, C. X.; Zhou, Q.; Sun, Y.; Sun, Y.; Xu, H. L.; Gao, J. S. Spectrosc. Let. 2020, 53, 360.

关键词

吡咯类杀菌剂;3D-QSAR

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