Synthesis of Novel 3-Aryl-isoxazoles Bearing 5-Aryloxymethyl or 5-Arylaminomethyl Linkage System as Potential Pesticides

doi:10.6023/cjoc201505047

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (12): 2595-2603.DOI: 10.6023/cjoc201505047 Previous Articles Next Articles

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具有5-芳氧甲基(芳胺甲基)链接的3-芳基异噁唑衍生物的合成及其生物活性初探

徐姗姗^a, 张敏^a, 张丽^a, 蒋海芳^a, 朱宁^a, 宋力平^a,b, 邓红梅^c

a 上海大学理学院化学系上海 200444;
b 中国科学院上海有机化学研究所有机氟化学重点实验室上海 200032;
c 上海大学微结构重点实验室上海 200444

收稿日期:2015-05-28 修回日期:2015-06-22 发布日期:2015-08-25
通讯作者: 张敏, 宋力平 E-mail:mzhang@shu.edu.cn;lpsong@shu.edu.cn
基金资助:
国家自然科学基金(Nos. 21272153, 21072128)资助项目.

Synthesis of Novel 3-Aryl-isoxazoles Bearing 5-Aryloxymethyl or 5-Arylaminomethyl Linkage System as Potential Pesticides

Xu Shanshan^a, Zhang Min^a, Zhang Li^a, Jiang Haifang^a, Zhu Ning^a, Song Liping^a,b, Deng Hongmei^c

a Department of Chemistry, School of Science, Shanghai University, Shanghai 200444;
b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032;
c Laboratory for Microstructures, Shanghai University, Shanghai 200444

Received:2015-05-28 Revised:2015-06-22 Published:2015-08-25
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21272153, 21072128).

1. Synthesis of Novel 3-Aryl-isoxazoles Bearing 5-Aryloxymethyl or 5-Arylaminomethyl Linkage System as Potential Pesticides.PDF(3309KB)

Abstract

A new class of 3-aryl-5-aryloxymethylisoxazole derivatives and 3-aryl-5-arylaminomethyl (or 5-benzylamino- methyl) isoxazole derivatives were designed and efficiently synthesized by nucleophilic substitution reaction of 3-aryl-5-bro- momethylisoxazole (1) with the corresponding phenols or anilines (or benzyl amines), respectively. All of the target compounds were characterized by ¹H NMR, IR, MS and elemental analysis. Besides, a biological activity study was performed to evaluate the mortality of 3-aryl-5-aryloxy-methylisoxazoles (3) towards Aphis crassivora. Particularly, 3-(2-cyanophenyl)-5- (2-chrolophenoxymethyl)isoxazole (3p) demonstrated a moderate biological activity.

Key words: isoxazole derivatives, aryloxy(amino)methyl linkage, synthesis, insecticidal activity

Cite this article

Xu Shanshan, Zhang Min, Zhang Li, Jiang Haifang, Zhu Ning, Song Liping, Deng Hongmei. Synthesis of Novel 3-Aryl-isoxazoles Bearing 5-Aryloxymethyl or 5-Arylaminomethyl Linkage System as Potential Pesticides[J]. Chin. J. Org. Chem., 2015, 35(12): 2595-2603.

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具有5-芳氧甲基(芳胺甲基)链接的3-芳基异噁唑衍生物的合成及其生物活性初探

Synthesis of Novel 3-Aryl-isoxazoles Bearing 5-Aryloxymethyl or 5-Arylaminomethyl Linkage System as Potential Pesticides

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