新型取代3-[(5-苄硫-1,3,4-噁二唑-2-基)甲基]苯并[d]噻(噁)唑-2(3H)-酮的合成及杀菌活性
收稿日期: 2014-10-31
修回日期: 2014-12-14
网络出版日期: 2015-01-07
基金资助
国家自然科学基金(No.30900959)和浙江省公益性(No.2014C31127)资助项目.
Synthesis and Antifungal Activity of Novel 3-[(5-Benzylthio- 1,3,4-oxadiazol-2-yl)methyl]benzo[d]thiazol- (oxazol)-2(3H)-ones
Received date: 2014-10-31
Revised date: 2014-12-14
Online published: 2015-01-07
Supported by
Project supported by the National Natural Science Foundation of China (No.30900959) and Public Project of Zhejiang Province (No.2014C31127).
为寻找新型高效杂环农药先导化合物, 以取代苯并噻(噁)唑酮为原料, 经取代、肼化、环化、苄基化反应合成了21个新型取代3-[(5-苄硫-1,3,4-噁二唑-2-基)甲基]苯并[d]噻(噁)唑-2(3H)-酮类化合物, 并利用1H NMR, IR, EI-MS及元素分析对其结构进行表征. 初步生物活性试验结果表明, 在50 mg/L浓度下, 大部分化合物对黄瓜炭疽病菌(Colletotrichum orbiculare), 灰葡萄孢菌(Botrytis cinerea)和水稻纹枯病菌(Rhizoctonia solani)具有中等杀菌活性, 其中化合物5b对灰葡萄胞菌和水稻纹枯病菌的抑制率均达到了85%以上.
阮铃莉 , 范人杰 , 刘幸海 , 陈杰 , 翁建全 . 新型取代3-[(5-苄硫-1,3,4-噁二唑-2-基)甲基]苯并[d]噻(噁)唑-2(3H)-酮的合成及杀菌活性[J]. 有机化学, 2015 , 35(5) : 1166 -1172 . DOI: 10.6023/cjoc201410041
In order to find novel biologically active pesticide lead compounds, twenty-one novel 3-[(5-benzylthio-1,3,4- oxadiazol-2-yl)methyl]benzo[d]thiazol(oxazol)-2(3H)-ones were synthesized by 2-benzothiazolinone/benzoxazolone as starting materials via substitution, hydrazine, cyclization and the last benzylation reaction. The structures of the title compounds were characterized by 1H NMR, IR, EI-MS and elemental analysis. The preliminary bioassay results indicated that most of them showed moderate inhibition activity against Colletotrichum orbiculare, Botrytis cinerea and Rhizoctonia solani at 50 mg/L, and the inhibition rate of compound 5b against Botrytis cinerea and Rhizoctonia solani reached above 85%.
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