新型吡唑基取代的甲磺酰基类化合物的合成及除草活性研究

引用本文: 温彦鹏, 张爽, 侯广峰, 于颖慧, 高金胜. 新型吡唑基取代的甲磺酰基类化合物的合成及除草活性研究[J]. 有机化学, 2016, 36(3): 642-647. doi: 10.6023/cjoc201508008 shu

Citation: Wen Yanpeng, Zhang Shuang, Hou Guangfeng, Yu Yinghui, Gao Jinsheng. Syntheses and Herbicidal Activities of New Methylsulfonyl Compounds with Pyrazol Group[J]. Chinese Journal of Organic Chemistry, 2016, 36(3): 642-647. doi: 10.6023/cjoc201508008 shu

新型吡唑基取代的甲磺酰基类化合物的合成及除草活性研究

温彦鹏 ^a, ,
张爽 ^b, ,
侯广峰 ^b, ,
于颖慧 ^{a,b,
,} ,
高金胜 ^{a,b,
,}

1.
a 黑龙江大学化学化工与材料学院哈尔滨 150080;
2.
b 黑龙江大学农药工程中心哈尔滨 150080

通讯作者: 于颖慧, 高金胜; 于颖慧, 高金胜

基金项目:
国家自然科学基金(No. 21371052) (No. 21371052)

黑龙江省博士后科研启动基金(No. LBH-Q14138)资助项目. (No. LBH-Q14138)

摘要: 为获得具有新颖结构和较高药效的新型除草剂, 基于环磺酮的结构, 对环磺酮结构中苯环的间位取代基及环己二酮环进行了修饰替换, 设计了6个新型的含有吡唑基的甲磺酰基类杂环化合物. 以2-甲基-3-氯苯胺起始原料, 经重氮化、乙酰基化、两步氧化、酯化、溴化、亲核取代、氯化、缩合等9步反应最终获得6个目标化合物. 最终产物以及重要中间体的结构采用¹H NMR、¹³C NMR、FTIR、元素分析等方法进行表征与确认. 对该6个化合物的除草活性进行了测试, 结果表明各化合物对芥菜、繁缕、看麦娘、小藜、棒头草均表现出良好的除草效果.

关键词:

English

Syntheses and Herbicidal Activities of New Methylsulfonyl Compounds with Pyrazol Group

1.
a School of Chemistry and Materials Science, Heilongjiang University, Harbin 150080;
2.
b Engineering Research Center of Pesticide of Heilongjiang University, Heilongjiang University, Harbin 150080

Corresponding author: 于颖慧, 高金胜; 于颖慧, 高金胜

Received Date: 07 August 2015
Available Online: 16 November 2015
Fund Project:
国家自然科学基金(No. 21371052)

黑龙江省博士后科研启动基金(No. LBH-Q14138)资助项目.

Abstract: To obtain new herbicidal candidates with novel structure and high herbicidal activities, six new pyrazol compounds based on the structure of tembotrione were designed and synthesized. The meta substituent of benzene ring and the cyclohexadione ring in the original tembotrione structure are replaced. The six target compounds were achieved with 3-chloro-2-methylaniline as the starting material after nine steps reactions, namely diazotization, acetylization, oxidation, esterization, bromization, nucleophilic substitution, chlorination and condensation reactions. All the structures of target products and their intermediates are characterized and confirmed by ¹H NMR, ¹³C NMR, FTIR and elemental analysis. Herbicidal activity tests are also conducted for the six compounds. The results show that each compound exhibits certain herbicidal activity toward mustard, chickweed, amur foxtail, chenopodium and polypogon fugax.

Key words:

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1.
沈阳化工大学材料科学与工程学院沈阳 110142

新型吡唑基取代的甲磺酰基类化合物的合成及除草活性研究

通讯作者: 于颖慧, 高金胜; 于颖慧, 高金胜

English

Syntheses and Herbicidal Activities of New Methylsulfonyl Compounds with Pyrazol Group

Corresponding author: 于颖慧, 高金胜; 于颖慧, 高金胜

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

新型吡唑基取代的甲磺酰基类化合物的合成及除草活性研究

通讯作者: 于颖慧, 高金胜; 于颖慧, 高金胜

English

Syntheses and Herbicidal Activities of New Methylsulfonyl Compounds with Pyrazol Group

Corresponding author: 于颖慧, 高金胜; 于颖慧, 高金胜

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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