Design, synthesis and fungicidal activity of 11-alkoxyimino-5,6-dihydro-dibenzo[b,e] azepine-6-one derivatives
文献类型: 外文期刊
第一作者: Xu, Yan-jun
作者: Xu, Yan-jun;Huang, Jia-xing;Liang, Xiao-mei;Zhang, Jian-jun;Wang, Dao-quan;Yan, Xiao-jing;Yuan, Hui-zhu
作者机构:
关键词: 5;6-dihydro-dibenzo[b;e]azepine-6-one;synthesis;fungicidal activity;structure-activity relationship
期刊名称:PEST MANAGEMENT SCIENCE ( 影响因子:4.845; 五年影响因子:4.674 )
ISSN:
年卷期:
页码:
收录情况: SCI
摘要: BACKGROUND: Macrocyclic compounds with an oxime ether side chain, discovered in Wang's group, showed good fungicidal activity. However, the long synthetic route makes the cost too high for them to be developed further as practical fungicides. Alternative compounds with good fungicidal activity and an easier synthesis than the above-mentioned macrolactams were sought, and a series of 11-alkoxyimino-5,6-dihydro-dibenzo[b,e]azepine-6-one derivatives (4) were designed and bioassayed. RESULTS: The structures were confirmed by ~1H NMR, ~(13)C NMR and LC-MS. The bioassay showed that about half of the 11-alkoxyimino-5,6-dihydro-dibenzo[b,e]azepine-6-one derivatives (4) displayed good fungicidal activity against Sclerotinia sclerotiorum (Lib.) de Bary, with EC_(50) values <15 μg ml~(-1), 11-(n-Butyloxyimino)-5,6-dihydro-dibenzo[b,e]azepine-6-one (4A-05), 11-(4-nitrobenzyloxyimino)-5,6-dihydro-dibenzo[b,e]azepine-6-one (4A-12) and 11-(2-chloro-6-fluorobenzyloxyimino)-5,6-dihydro-dibenzo[b,e]azepine-6-one (4A-21) displayed excellent fungicidal activity, with EC_(50) values of <2.5 μg mL~(-1), much better than the commercial fungicide chlorothalonil with an EC_(50) value of 7.16 μg mL~(-1). In addition, about half of the 11-alkoxyimino-5,6-dihydro-dibenzo[b,e]azepine-6-one derivatives (4) had good fungicidal activity against Botrytis cinerea (De Bary) Whetzel, with EC_(50) values of <10 μg mL~(-1).11-(2-Fluorobenzyloxyimino)-5,6-dihydro-dibenzo[b,e]azepine-6-one (4A-16), 11-(3-fluorobenzyloxyimino)-5,6-dihydro-dibenzo[b,e]azepine-6-one (4A-17) and 11-(2-chloro-6-fluorobenzyloxyimino)-5,6-dihydro-dibenzo[b,e]azepine-6-one (4A-21) displayed excellent fungicidal activity, with EC_(50) values of 3.73, 2.54 and 3.20 μg mL~(-1) respectively, comparable with the commercial fungicide procymidon with an EC_(50) value of 2.45 μg mL~(-1). Their structure-activity relationship is discussed. CONCLUSIONS: The present work demonstrates that the title compounds show promise as fungicides.
分类号: S4
- 相关文献
作者其他论文 更多>>
-
Honey bee (Apis cerana) queen rearing methods influence queen morphological characteristics and reproductive related gene expression
作者:Zhong, Wei-Lai;Ding, Gui-Ling;Huang, Jia-Xing;Feng, Mao;Yuan, Chun-Ying
关键词:Apis cerana; queen rearing; queen quality; gene expression
-
Piperonyl-Tethered Rhodanine Derivatives Potently Inhibit Chitinolytic Enzymes of Ostrinia furnacalis
作者:Han, Qing;Liu, Yao-Yang;Zhang, Jing-Yu;Zhang, Ru-Lei;Li, Hui-Lin;Jiang, Zhi-Yang;Huang, Jia-Xing;Duan, Hong-Xia;Wu, Nan;Yang, Qing;Yang, Qing;Yang, Qing
关键词:piperonyl-tethered rhodanine derivatives; chitinase; chitinase inhibitor; insect growth and regulator; pesticide
-
Decline of three farmland pest species in rapidly urbanizing landscapes
作者:Wan, Nian-Feng;Wang, Jin-Yan;Ji, Xiang-Yun;Cai, You-Ming;Jiang, Jie-Xian;Wan, Nian-Feng;Ma, Jun;Qiu, Shi-Yun;Li, Bo;Wan, Nian-Feng;Ma, Jun;Qiu, Shi-Yun;Li, Bo;Dainese, Matteo;Zhu, Feng;Wang, Mao-Tao;Zhou, Chen;Xiao, Liu-Bin;Zhang, Wei;Wang, Wei-Min;Zhu, Jian-Wen;Cheng, Wei;Jiang, Yao-Pei;Wu, Xiang-Wen;Shen, Hui-Mei;Chen, Shi-Jian;Wei, Qin;Yi, Hong-Juan;Gan, Hui-Hua;Lu, Yi;Zhou, Zi-Ji;Zhang, Jian-Jun;Chen, Wei-Yu
关键词:
-
Synthesis and fungicidal activity of novel 2,5-disubstituted-1,3,4-thiadiazole derivatives containing 5-phenyl-2-furan
作者:Li, Ya-Sheng;Hu, De-Kun;Tian, Hao;Wang, Yuan;Jiang, Jia-Zhen;Yan, Xiao-Jing
关键词:
-
Molecular characterization and tissue localization of sensory neuron membrane protein from Chinese honey bee, Apis cerana cerana (Hymenoptera: Apidae)
作者:Hu, Ying-Ying;Xu, Shu-Fa;Wubie, Abebe Jenberie;Li, Wei;Huang, Jia-Xing;Guo, Zhan-Bao;Zhou, Ting;Wubie, Abebe Jenberie
关键词:Apis cerana cerana;SNMP;Tissue distribution;Western blot;Immunohistochemistry
-
Nucleotide variation in ATHK1 region of Arabidopsis thaliana and its association study with drought tolerance
作者:Zhang, Jian-Jun;Hao, Gang-Ping;Wu, Zhong-Yi;Zhang, Xiu-Hai;Wang, Yong-Qin;Cao, Ming-Qing;Huang, Cong-Lin;Zhang, Jian-Jun;Liu, Shi-Gui;Hao, Gang-Ping;Yang, Qing
关键词:Arabidopsis;ATHK1;nucleotide variation;drought tolerance;association study
-
Synthesis and fungicidal activity of macrolactams and macrolactones with an oxime ether side chain
作者:Jia, Yue-Mei;Liang, Xiao-Mei;Zhu, Wei-Juan;Zhang, Jian-Jun;Dong, Yan-Hong;Wu, Jin-Ping;Chen, Fu-Heng;Wang, Dao-Quan;Yuan, Hui-Zu;Qi, Shu-Hua
关键词:macrolactam;macrolactone;synthesis;fungicidal activity;fungicide;pesticide