Design, Synthesis, Crystal Structure, and Fungicidal Activity of L-Carvone Derivatives Containing an Oxime Ester Moiety
Design, Synthesis, Crystal Structure, and Fungicidal Activity of L-Carvone Derivatives Containing an Oxime Ester Moiety
复制标题
含肟酯部分的L-香芹酮衍生物的设计、合成、晶体结构和杀菌活性
DOI：
10.6023/cjoc202010028
复制
发表时间：
2021-05-25
影响因子：
1.9
通讯作者：
Zhou, Xiaomao
中科院分区：
文献类型：
--
作者：
Jin, Can;Deng, Xile;Zhou, Xiaomao
L-香芹酮是一种具有杀菌活性的天然产物，可作为筛选新型杀菌剂的先导化合物。以L-香芹酮为先导化合物，采用活性亚结构拼接策略，合成了一系列含肟酯基的L-香芹酮衍生物。通过IR、H-1 NMR、C-13 NMR和HRMS等手段对L-香芹酮衍生物的结构进行了表征。对5种植物病原真菌，即核盘菌（Sclerotinia sclerotiorum）、禾谷镰刀菌（Fusarium graminearum）、稻瘟病菌（Pyricularia grisea）、尖孢镰刀菌（Fusariwn oxysporum）和黄瓜枯萎病菌（Thanatephorus cucumeris）进行了活性评价。结果表明，大部分化合物具有较好的抗真菌活性。其中，（E）-2-甲基-5-（丙-1-烯-2-基）环己-2-烯-1-酮O-4-乙基苯甲酰基肟（4 e）对禾谷镰刀菌的杀菌活性最好（EC 50 =5.07 mg/L），和（S，E）-2-甲基-5-（丙-1-烯-2-基）环己-2-烯-1-酮O-（3-甲基苯甲酰基）肟（4 b）对油菜菌核病菌的抑制效果最好，EC 50 =18.84 mg/L，优于市售杀菌剂烯肟菌酯。因此，L-香芹酮衍生物具有开发新型杀菌剂的潜力。
L-Carvone is a natural product with fungicidal activity, which can be used as a lead compound for screening new fungicides. A series of L-carvone derivatives containing an oxime ester moiety were synthesized by splicing active substructure strategy with L-carvone as the lead compound. The structures of the L-carvone derivatives were characterized by IR, H-1 NMR, C-13 NMR and HRMS analyses. The antifungal activities of these compounds were evaluated against five plant pathogenic fungi, namely Sclerotinia sclerotiorum, Fusarium graminearum, Pyricularia grisea, Fusariwn oxysporum and Thanatephorus cucumeris. The results indicated that most of the compounds showed good antifungal activities. Among them, (E)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one O-(4-ethylbenzoyl)oxime (4e) had the best fungicidal activity against Fusarium graminearum (EC50=5.07 mg/L), and (S,E)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one O-(3-methylbenzoyl)oxime (4b) had the best fungicidal activity against Sclerotinia sclerotiorum, (EC50=18.84 mg/L), which were better than the commercial fungicide enestroburin. Therefore, L-carvone derivatives have the potential to develop new fungicides.