含噁二唑结构的甲氧基丙烯酸酯类杀菌剂的合成及生物活性研究
收稿日期: 2016-07-19
修回日期: 2016-09-12
网络出版日期: 2016-10-18
基金资助
高等学校学科创新引智计划（No.B06005）、元素有机化学国家重点实验室和天津化学化工协同创新中心资助项目.
Design, Synthesis and Bioactivities of Novel Strobilurin Derivatives Containing 1,3,4-Oxadiazole Moity
Received date: 2016-07-19
Revised date: 2016-09-12
Online published: 2016-10-18
Supported by
Project by the “111” Project of Ministry of Education of China (No. B06005), the State Key Laboratory of Elemento-organic Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin).
基于生物电子等排和活性亚结构拼接原理，设计合成了16个结构新颖，含噁二唑结构的甲氧基丙烯酸酯类杀菌剂，化合物结构均已通过核磁共振氢谱、碳谱和高分辨质谱确证，并对其进行了离体杀菌活性测试.结果表明：部分化合物对于油菜菌核病菌的活性与对照药嘧菌酯相当，部分化合物对于小麦纹枯病菌活性超过对照药嘧菌酯.进行了初步的构效关系研究.（E）-2-{2-[4-（噁二唑-2-基）苯基硫甲基]苯基}-3-甲氧基丙烯酸甲酯（IIa）和（E）-2-{2-[4-（5-乙基噁二唑-2-基）苯基硫甲基]苯基}-3-甲氧基丙烯酸甲酯（IIc）对于多种真菌表现很好的抑制活性，可作为先导化合物进一步研究.
关键词： 1,3,4-噁二唑; 甲氧基丙烯酸酯类杀菌剂; 离体; 杀菌活性
刘阳 , 刘明 , 陈明桂 , 吴长春 , 华学文 , 周莎 , 王宝雷 , 李正名 . 含噁二唑结构的甲氧基丙烯酸酯类杀菌剂的合成及生物活性研究[J]. 有机化学, 2017 , 37(2) : 403 -410 . DOI: 10.6023/cjoc201607029
A series of novel strobilurin derivatives containing 1,3,4-oxdiazole moity were designed and synthesized based on the bioisosterism and coordination of active substructure theories. The structures of new compounds were characterized by 1H NMR, 13C NMR and HRMS spectra. The bioassay indicated that the fungicidal activities of some compounds against Sclerotinia sclerotiorum reached the activity of azoxystrobin as the control and some compounds against Rhizotonia cerealis in vitro were more effective than the same control. Their structure-activity relationship was discussed. Methyl (E)-2-(2-((4-(1,3,4-oxadiazol-2-yl)phenoxy)methyl)phenyl)-3-methoxyacrylate (IIa) and methyl (E)-2-(2-((4-(5-ethyl-1,3,4-oxadiazol-2-yl)phe-noxy)methyl)phenyl)-3-methoxyacrylate (IIc) could be considered as leading compounds for further investigation.
Key words： 1,3,4-oxdiazole; strobilurin; in vitro; fungicidal activity
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