Synthesis and Unexpected Insecticidal Activity of (E)-3-(1-Imino-ethyl)-5,5-disubstituted-4-(methylamino)furan-2(5H)-one

doi:10.6023/cjoc202004050

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (8): 2547-2554.DOI: 10.6023/cjoc202004050 Previous Articles Next Articles

(E)-3-(1-亚胺基乙基)-5,5-二取代-4-甲氨基呋喃-2(5H)-酮的合成及其意外的杀虫活性

赵宇, 刘鑫磊, 李益豪, 许磊川, 苏彦豪, 蒋家珍, 王明安

中国农业大学应用化学系农药创新研究中心北京 100193

收稿日期:2020-04-29 修回日期:2020-05-10 发布日期:2020-05-29
通讯作者: 王明安 E-mail:wangma@cau.edu.cn
基金资助:
国家自然科学基金（No.21772229）资助项目.

Synthesis and Unexpected Insecticidal Activity of (E)-3-(1-Imino-ethyl)-5,5-disubstituted-4-(methylamino)furan-2(5H)-one

Zhao Yu, Liu Xinlei, Li Yihao, Xu Leichuan, Su Yanhao, Jiang Jiazhen, Wang Ming'an

Innovation Center of Pesticide Research, Department of Applied Chemistry, China Agricultural University, Beijing 100193

Received:2020-04-29 Revised:2020-05-10 Published:2020-05-29
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21772229).

1. cjoc202004050辅助材料.pdf(1649KB)

Abstract

In order to improve the fungicidal activity against phytopathogens and enlarge the constructed molecular library, eighteen novel (E)-3-(1-iminoethyl)-5,5-disubstituted-4-(methylamino)-furan-2(5H)-ones were designed and synthesized based on the diversity-oriented synthesis strategy when the C-4 phenyl group of 3-(1-iminoethyl)-5,5-disubstituted-4-phenylfuran-2(5H)-one was replaced with the methylamino group. Their structures were characterized by ¹H NMR, ¹³C NMR, HR-MS spectral data. The crystal structure of (E)-3-(1-((4-methoxybenzyloxy)imino)ethyl)-4-(methylamino)-1-oxaspiro[4.5]dec-3-en-2-one (5O) was determined by X-ray diffraction analysis. The bioassay results indicated that all compounds did not exhibit significant in vivo fungicidal activities against phytopathogens, but some of them showed good insecticidal activities against Plutella xylostella, Mythimna seprata and Myzus persicae with 100% mortality at the concentration of 600 μg/mL.

Key words: (E)-3-(1-iminoethyl)-5,5-disubstituted-4-(methylamino)furan-2(5H)-one, diversity-oriented synthesis, oxime ether scaffold, insecticidal activity

Cite this article

Zhao Yu, Liu Xinlei, Li Yihao, Xu Leichuan, Su Yanhao, Jiang Jiazhen, Wang Ming'an. Synthesis and Unexpected Insecticidal Activity of (E)-3-(1-Imino-ethyl)-5,5-disubstituted-4-(methylamino)furan-2(5H)-one[J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2547-2554.

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(E)-3-(1-亚胺基乙基)-5,5-二取代-4-甲氨基呋喃-2(5H)-酮的合成及其意外的杀虫活性

Synthesis and Unexpected Insecticidal Activity of (E)-3-(1-Imino-ethyl)-5,5-disubstituted-4-(methylamino)furan-2(5H)-one

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