Mannich反应合成3,6(8)-二取代-2,4-二氢-1,3-苯并□嗪及其杀菌活性

引用本文: 唐子龙, 夏赞稳, 马红伟, 刘汉文, 欧晓明. Mannich反应合成3,6(8)-二取代-2,4-二氢-1,3-苯并□嗪及其杀菌活性[J]. 应用化学, 2013, 30(9): 993-998. doi: 10.3724/SP.J.1095.2013.20507 shu

Citation: TANG Zilong, XIA Zanwen, MA Hongwei, LIU Hanwen, OU Xiaoming. Synthesis of 3,6(8) -Disubstituted-2,4-Dihydro-1,3 benzoxazines via Mannich Reaction and Their Fungicidal Activities[J]. Chinese Journal of Applied Chemistry, 2013, 30(9): 993-998. doi: 10.3724/SP.J.1095.2013.20507 shu

Mannich反应合成3,6(8)-二取代-2,4-二氢-1,3-苯并□嗪及其杀菌活性

a. 湖南科技大学化学化工学院, 湘潭 411201;
b. 湖南科技大学理论化学与分子模拟省部共建教育部重点实验室, 湘潭 411201;
c. 湖南科技大学分子构效关系湖南省高校重点实验室, 湘潭 411201;
d. 湖南化工研究院国家农药创制工程技术研究中心, 长沙 410014
基金项目:
国家自然科学基金资助项目(21042011)

湖南省教育厅重点项目(10A034)

国家科技支撑计划项目子课题(2011BAE06B01)

理论化学与分子模拟省部共建教育部重点实验室开放基金课题(LKF1103)

摘要: 以取代苯酚、多聚甲醛和取代苯胺为原料,在无催化剂的条件下,通过Mannich缩合反应合成了一系列新型3,6(8)-二取代-2,4-二氢-1,3-苯并□嗪类化合物。结果表明,取代苯酚和取代苯胺的取代基为供电子基时,合成产物的产率高于吸电子取代基的。产物的结构用¹H NMR、¹³C NMR、IR和MS等进行了表征。初步测试了目标化合物的杀菌活性,部分化合物具有较好的杀菌活性。当浓度为25 mg/L时,化合物4j和4d对菌核病菌的抑制率分别为86.1%和81.5%,化合物4i对灰霉病菌的抑制率为81.6%。

关键词:

English

Synthesis of 3,6(8) -Disubstituted-2,4-Dihydro-1,3 benzoxazines via Mannich Reaction and Their Fungicidal Activities

a. School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China;
b. Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education, Hunan University of Science and Technology, Xiangtan 411201, China;
c. Hunan Provincial University, Key Laboratory of QSAR/QSPR Hunan University of Science and Technology, Xiangtan 411201, China;
d. National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410014, China
Received Date: 06 November 2012
Revised Date: 15 January 2013

Abstract: A series of novel 3,6(8)-disubstituted 2,4-dihydro-1,3-benzoxazines was synthesized by Mannich reactions of substituted anilines with paraformaldehyde and substituted phenols in the absence of catalyst. The results show that substituted phenols and anilines with electron-donating groups on the phenyl ring give higher yields than those with electron-withdrawing groups. The structures of the products were characterized by ¹H NMR,¹³C NMR,IR and MS. The fungicidal activity of the title compounds was preliminarily evaluated.Compounds 4j and 4d show 86.1% and 81.5% activity against Sclerotonia sclerotiorum at the concentration of 25 mg/L,respectively. Compound 4i exhibits 81.6% activity against Botrytis cinerea.

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Mannich反应合成3,6(8)-二取代-2,4-二氢-1,3-苯并□嗪及其杀菌活性

English

Synthesis of 3,6(8) -Disubstituted-2,4-Dihydro-1,3 benzoxazines via Mannich Reaction and Their Fungicidal Activities

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中国化学会秘书处

Mannich反应合成3,6(8)-二取代-2,4-二氢-1,3-苯并□嗪及其杀菌活性

English

Synthesis of 3,6(8) -Disubstituted-2,4-Dihydro-1,3 benzoxazines via Mannich Reaction and Their Fungicidal Activities

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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通讯作者: 陈斌, bchen63@163.com

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