摘要/Abstract

为探究具有生物活性的先导化合物，以氟噻唑吡乙酮为模板，设计并合成了16个未见文献报道的氟噻唑吡乙酮类衍生物，初步研究了在噻唑环上与硫相邻碳（5号碳）上取代基的变化对抑菌活性的影响.其结构经¹H NMR、¹³C NMR和HRMS确证，测试表明：在100 μg/mL的浓度下目标化合物普遍具有杀菌活性，其中1-（4-（4-环丙基-5-（2-氟苯基）噻唑-2-基）哌啶-1-基）-2-（5-甲基-3-三氟甲基-1H-吡唑-1-基）乙-1-酮（9o）对小麦赤霉病的抑制率为60%；6个化合物对苹果褐斑病的抑制率为70%；4个化合物对对马铃薯晚疫病的抑制率为50%；2-（5-甲基-3-三氟甲基-1H-吡唑-1-基）-1-（4-（4-甲基-5-（间甲基苯基）噻唑-2-基）哌啶-1-基）乙-1-酮（9h）对黄瓜灰霉病的抑制率为75%.并且在100 μg/mL浓度下目标化合物对苹果褐斑病、黄瓜灰霉病抑制效果.要高于对照药品嘧菌酯在50 μg/mL时的抑菌活性.
关键词: 氟噻唑吡乙酮, 噻唑, 杀菌活性
In order to explore the structure of lead compounds with biological activities, using oxathiapiprolin as a template, sixteen oxathiapiprolin derivatives were designed and synthesized to study the influences of substituent to the fungicidal activities which connected with carbon (No. 5 carbon) near the sulfur on the thiazole ring. All the structures were confirmed by ¹H NMR, ¹³C NMR and HRMS. Preliminary bioassay showed that the target compounds generally had fungicidal activitives in vitro at a concentration of 100 μg/mL, the fungicidal activities of 1-(4-(4-cyclopropyl-5-(2-fluorophenyl)thiazol-2-yl)piperidin- 1-yl)-2-(5-methyl-3-trifluoromethyl-1H-pyrazol-1-yl)ethan-1-one (9o) against Fusarium graminearum was 60%, the fungicidal activities of six target compounds against Diplocarpon mali were 70%, the fungicidal activities of four target compounds against Phytophthora infestans were 50%, and the fungicidal activities of 2-(5-methyl-3-trifluoromethyl-1H-pyrazol-1- yl)-1-(4-(4-methyl-5-(m-tolyl)thiazol-2-yl)piperidin-1-yl)ethan-1-one (9h) against Botrytis cinerea was 75%. In addtion, the fungicidal activities of the target compounds aganist Diplocarpon mali and Botrytis cinerea at 100 μg/mL were higher to azoxystrobin at 50 μg/mL.
Key words: oxathiapiprolin, thiazole, fungicidal activity


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