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第五十三分會：農(nóng)業(yè)化學(xué)與農(nóng)產(chǎn)品

摘要

新型吡咯類殺菌劑合成設(shè)計及其3D-QSAR研究 徐洪亮1，蘇靜2，侯晨忻3，馬騰飛4，朱曉磊5，王子時1,* 1黑龍江大學(xué)，黑龍江省哈爾濱市，150080 2華中師范大學(xué)，湖北省武漢市，430070 *Email: Wangzishi7@hlju.edu.cn 為尋找具有更高生物活性、更環(huán)保的新型綠色農(nóng)藥，本文基于殺菌劑氟咯菌腈設(shè)計并合成了21個苯基吡咯類化合物，其中8個化合物的結(jié)構(gòu)未見文獻(xiàn)報道，15個化合物的殺菌活性未被文獻(xiàn)報道。 目標(biāo)化合物以取代的苯甲醛為原料進行合成，并在吡咯環(huán)上引入甲基基團，其目的是探究其殺菌活性的變化。本文采用1H NMR、FTIR、單晶X-射線衍射、元素分析和熔點測定等測試手段對目標(biāo)化合物及其中間體的結(jié)構(gòu)進行了表征與確認(rèn)，并通過揮發(fā)法培養(yǎng)得到10個苯基吡咯類化合物的單晶結(jié)構(gòu)。生物活性測試結(jié)果顯示：在1 mg/L和10 mg/L濃度條件下，該類化合物對Fusarium moniliforme、Rhizoctonia solani、Pyricularia oryzae、Fusarium oxysporum表現(xiàn)出較好的抑菌活性，體現(xiàn)了廣譜性的殺菌效果，而氮位甲基取代的目標(biāo)化合物則只對Rhizoctonia solani表現(xiàn)出較好的抑菌活性，這正由于在吡咯環(huán)上引入了甲基基團導(dǎo)致該類化合物的生物活性出現(xiàn)明顯變化，從而表現(xiàn)出專一性的特點?；谏鲜銮闆r對所合成的21個化合物的殺菌活性進行3D-QSAR研究。將Rhizoctonia solani得到的IC50值轉(zhuǎn)化成pIC50值進行數(shù)據(jù)集的測試。采用比較分子力場分析 (CoMFA)方法，建立了三維定量構(gòu)效關(guān)系CoMFA模型 (q2＝0.503，r2＝0.974)。CoMFA模型的立體場、靜電場、三維等勢圖非常直觀地解釋了結(jié)構(gòu)與殺菌活性的關(guān)系，展現(xiàn)了較好的預(yù)測能力，也為后續(xù)該系列化合物的進一步優(yōu)化提供了理論支持。 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 關(guān)鍵詞：吡咯類化合物；殺菌劑；氮位取代；生物活性；3D-QSAR 參考文獻(xiàn) [1] 王子時, 葉漢韜, 肖丹, 馬東升, 高金勝, 于穎慧, 侯廣峰, 閆鵬飛. Chin. J. Org. Chem. 2014, 34: 2057. [2] 王子時, 路運才, 吳鵬沖, 李麗, 高金勝. 一種氮位取代苯基吡咯類化合物及其在植物殺菌中的用途[P]. 申請?zhí)? 202010335383.3, 黑龍江大學(xué), 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] 王子時, 葉漢韜, 肖丹, 馬東升, 高金勝, 于穎慧, 侯廣峰, 閆鵬飛. Chin. J. Org. Chem. 2014, 34: 2057. [2] 王子時, 路運才, 吳鵬沖, 李麗, 高金勝. 一種氮位取代苯基吡咯類化合物及其在植物殺菌中的用途[P]. 申請?zhí)枺?02010335383.3, 黑龍江大學(xué), 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.

關(guān)鍵詞

吡咯類殺菌劑;3D-QSAR

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