氟噻唑吡乙酮类衍生物的合成及杀菌活性
收稿日期: 2019-01-07
修回日期: 2019-02-27
网络出版日期: 2019-03-29
基金资助
浙江省绿色农药2011协同创新中心开放基金资助项目.
Synthesis and Fungicidal Activity of Novel Oxathiapiprolin Derivatives
Received date: 2019-01-07
Revised date: 2019-02-27
Online published: 2019-03-29
Supported by
Project supported by the Collaborative Innovation Center of Zhejiang Province Green Pesticide
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.
丁成荣 , 潘亚运 , 殷许 , 谭成侠 , 王学东 . 氟噻唑吡乙酮类衍生物的合成及杀菌活性[J]. 有机化学, 2019 , 39(7) : 2062 -2069 . DOI: 10.6023/cjoc201901009
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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