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2014 , Vol. 34 >Issue 1: 118 - 125

DOI: https://doi.org/10.6023/cjoc201307017

研究论文

N-氮杂环甲氧基-O-（4-芳氧基苯基）乳酸酰胺的合成与除草活性

  • 刘祈星 ,
  • 黄明智 ,
  • 柳爱平 ,
  • 聂思桥 ,
  • 雷满香 ,
  • 任叶果 ,
  • 裴晖 ,
  • 何丽英 ,
  • 胡礼 ,
  • 胡艾希
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  • a 湖南大学化学化工学院 长沙 410082;
    b 湖南化工研究院 国家农药创制工程技术研究中心 长沙 410007

收稿日期: 2013-07-12

  修回日期: 2013-09-12

  网络出版日期: 2013-09-30

基金资助

国家重点基础研究发展计划（97计划，No. 2010CB126104）；国家教育部博士点专项基金（No. 20040532002）；湖南省自然科学基金（No. 11JJ2006）资助项目.

收起

Synthesis and Herbicidal Activity of Novel N-Hetrocyclo Containing Nitrogen Methoxy-O-(4-aryloxy-phenyl) Lactamide Derivatives

  • Liu Qixing ,
  • Huang Mingzhi ,
  • Liu Aiping ,
  • Nie Siqiao ,
  • Lei Manxiang ,
  • Ren Yeguo ,
  • Pei Hui ,
  • He Liying ,
  • Hu Li ,
  • Hu Aixi
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  • a College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082;
    b National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007

Received date: 2013-07-12

  Revised date: 2013-09-12

  Online published: 2013-09-30

Supported by

Project supported by the National Basic Research Program of China (973 Program, No. 2010CB126104), the National Research Foundation for the Doctoral Program of Higher Education of China (No. 20040532002), the Natural Science Foundation of Hunan Province (No. 11JJ2006).

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摘要

以A8169为先导，设计并合成了12个新型的N-氮杂环甲氧基-O-（4-芳氧基苯基）乳酸酰胺化合物，其结构经1H NMR，13C NMR，LC/MS和IR确证. 初步生物活性测定结果表明，化合物在2250 g/ha剂量下，对单子叶杂草马唐（Digitaria sanguinalis）、稗草（Echinochloa crus-galli）、狗尾草（Setaria viridis）等均具有100%的除草活性，进一步活性筛选发现，（R）-（+）-N-[（2-氯噻唑-5-基）甲氧基]-O-[4-（（6-氯喹喔啉-2-基）氧基）苯氧基]乳酸酰胺（2f）除草活性（马唐IC50=6.8 g/ha，稗草IC50=6.6 g/ha）远高于同类商品化除草剂炔草酯和先导化合物A8169.

关键词： N-氮杂环甲氧基-O-（4-芳氧基苯基）乳酸酰胺; 合成; 除草活性

本文引用格式

刘祈星 , 黄明智 , 柳爱平 , 聂思桥 , 雷满香 , 任叶果 , 裴晖 , 何丽英 , 胡礼 , 胡艾希 . N-氮杂环甲氧基-O-（4-芳氧基苯基）乳酸酰胺的合成与除草活性[J]. 有机化学, 2014 , 34(1) : 118 -125 . DOI: 10.6023/cjoc201307017

Abstract

The lead compound A8169 was modified, 12 N-hetrocyclo containing nitrogen methoxy-O-(4-aryloxy-phenyl) lactamide derivatives were designed and synthesized, and their structures were characterized by 1H NMR, 13C NMR, LC/MS and IR. The bioassay results indicated that all compounds exhibited 100% activities against Digitaria sanguinalis, Echinochloa crus-galli L and Setaria Viridis at 2250 g/ha. In particular, (R)-(+)-N-((2-chlorothiazol-5-yl)methoxy)-O-(4-((6-chloro-quinoxalin-2-yl)oxy)phenoxy) lactamide (2f) was much more effective against Digitaria sanguinalis (IC50=6.8 g/ha) and Echinochloa crus-galli (IC50=6.6 g/ha) than commercial clodinafop-propargyl and lead compound A8169.

Key words： N-hetrocyclo containing nitrogen methoxy-O-(4-aryloxy-phenyl) lactamide; synthesis; herbicidal activity

参考文献

[1] Becker, W.; Langelueddeke, P.; Leditschke, H. DE 2223894, 1973 [Chem. Abstr. 1974, 80, 70543].

[2] Rogers, R. B.; Gerwick, B. C. US 4725683, 1988 [Chem. Abstr. 1989, 111,133787].

[3] Kover, J.; Szilagyi, L.; Antus, S. Heterocycl. Commun. 2002, 8, 237.

[4] Kim, D. W.; Chang, H. S.; Ko, Y. K.; Ryu, J. W.; Woo, J. C.; Koo, D. W.; Kim, J. S. US 20030096706, 2003 [Chem. Abstr. 2003, 138,364189].

[5] Liu, H.; Wang, H. Q.; Ding, M. W.; Liu, Z. J.; Xiao, W. J. J. Fluorine Chem. 2006, 127, 1584..

[6] Yu, Z. H.; Shi, D. Q. Phosphorus, Sulfur, Silicon Relat. Elem. 2010, 185, 2316.

[7] Tajik, H.; Dadras, A. J. Pestic. Sci. (Tokyo, Jpn.). 2011, 36, 27.

[8] Tajik, H.; Dadras, A.; Aghabeygi, S. Chin. Chem. Lett. 2011, 22, 535.

[9] Huang, T. H.; Tu, H. Y.; Aibibu, Z. ARKIVOC 2011, (ii), 1.

[10] Richard, B. R.; Gerwick, B. C. US 4725683, 1988 [Chem. Abstr. 1989, 111, 133787].

[11] James, A. T; Daniel J. P. J. Agric. Food Chem. 2002, 50, 4554.

[12] Wang, R. J.; Zheng, L. Y.; Yang, X. Y.; Yang, Y.; Wang, X. J.; Cao, S. G. Chem. J. Chin. Univ. 2011, 32, 2817 (in Chinese).

(王瑞俭, 郑良玉, 杨雪莹, 杨晔, 王晓娟, 曹淑桂, 高等学校化学学报, 2011, 32, 2817.)

[13] Wang, Q. M.; Li, H.; Li, Y. H.; Huang, R. Q. J. Agric. Food Chem. 2004, 52, 1918.

[14] Li, G. Y.; Qian, X. H.; Cui, J. G.; Huang, Q. C.; Zhang, R.; Guan, H. J. Agric. Food Chem. 2006, 54, 125.

[15] Dai, H.; Li, Y. Q.; Du, D.; Qin, X.; Zhang, X.; Yu, H. B.; Fang, J. X. J. Agric. Food Chem. 2008, 56, 10805.

[16] Yan, M.; Shi, D. Q.; Xiao, L. X. Chin. J. Org. Chem. 2008, 28, 1012 (in Chinese).

(严曼, 石德清, 肖琳霞, 有机化学, 2008, 28, 1012.)

[17] Xiao, L. X.; Shi, D. Q. Chin. J. Org. Chem. 2010, 30, 85 (in Chinese).

(肖琳霞, 石德清, 有机化学, 2010, 30, 85.)

[18] Yu, Z. H.; Shi, D. Q. J. Huazhong Normal Univ. (Nat. Sci.) 2011, 45, 249 (in Chinese).

(余治华, 石德清, 华中师范大学学报(自然科学版), 2011, 45, 249.)

[19] Liu, X. Y.; Kan, D. L.; Ding, X. C. Acta Chim. Sinica 2011, 69, 1445 (in Chinese).

(刘训悦, 阚登蕾, 丁兴成, 化学学报, 2011, 69, 1445.)

[20] Zeng, G. P.; Zheng, P. Acta Chim. Sinica 2012, 70, 759 (in Chinese).

(曾国平, 郑平, 化学学报, 2012, 70, 759.)

[21] Cheng, C. S.; Qin, F. T.; Wei, Z. Y.; Ren, Z. B.; Ming, X. Acta Chim. Sinica 2012, 70, 1227 (in Chinese).

(程春生, 秦福涛, 魏振云, 任忠宝, 明旭, 化学学报, 2012, 70, 1227.)

[22] Wang, T. T.; Miao, W. K.; Wu, S. S.; Bing, G. F.; Zhang, X.; Qin, Z. F.; Yu, H. B.; Qin, X.; Fang, J. X. Chin. J. Chem. 2011, 29, 959.

[23] Yan, T.; Yu, S. J.; Liu, P. F; Liu, Z.; Wang, B. L.; Xiong, L. X.; Li, Z. M. Chin. J. Chem. 2012, 30, 919.

[24] Schurter, R.; Rempfler, H. US 4713109, 1987 [Chem. Abst. 1988, 109, 128841].

[25] Liu, A. P.; Cheng, S. X.; Lei, M. X.; Yao, Y.; Hu, Z. B.; He, H. J.; Wu, Y. Y.; Xiang, J.; Liu, M. H. CN 101885703, 2010 [Chem. Abstr. 2010, 154, 30180].

[26] Liu, A. P.; Feng, Q. J.; Hu, C. H.; He, H. J.; Wang, T. J.; Liu, Y.; Lei, M. X.; Pang, H. L.; He, H. W. Chin. J. Org. Chem. 2008, 28, 531 (in Chinese).

(柳爱平, 冯秋菊, 胡春华, 何海军, 王婷瑾, 刘洋, 雷满香, 庞怀林, 贺红武, 有机化学, 2008, 28, 531.)

[27] Wei, Z. Z.; Pang, H. L.; Liu, Y.; Liu, A. P.; Cheng, H.; Ling, L. Z.; Hu, C. H.; Yang, G. F. Chin. J. Org. Chem. 2006, 26, 1120 (in Chinese).

(魏振中, 庞怀林, 刘洋, 柳爱平, 程华, 凌立志, 胡春华, 杨光富, 有机化学, 2006, 26, 1120.)

[28] Yi, K. H.; Fu, Y.; Ye, F. Plant Protection 2012, 38, 11 (in Chinese).

(衣克寒, 付颖, 叶非, 植物保护, 2012, 38, 11.)

[29] Huang, L.; He, H. J.; Liu, Q. X.;Lei, M. X.; Yu, S. Y.; Ren, Y. G.; Ou, X. M.; Huang, M. Z.; Liu, A. P. Fine Chem. Intermed. 2011, 41, 20 (in Chinese).

(黄路, 何海军, 刘祈星, 雷满香, 余淑英, 任叶果, 欧晓明, 黄明智, 柳爱平, 精细化工中间体, 2011, 41, 20.)

[30] Qin, Y. H. J. Ningbo Univ. (Nat. Sci. Eng. Ed.) 2007, 20, 381 (in Chinese).

(秦永华, 宁波大学学报(理工版), 2007, 20, 381.)

[31] Sugata, R.; Shashi, B. S. J. Environ. Sci. Health, Part B 2005, 40, 525.

[32] Yuan, H. L.; Liu, W. D.; Lan, Z. L.; Du, S. H. Fine Chem. Intermed. 2011, 41, 24 (in Chinese).

(袁海龙, 刘卫东, 兰支利, 杜升华, 精细化工中间体, 2011, 41, 24.)

[33] Moon, J. K.; Keum, Y. S.; Hwang, E. C.; Park, B. S.; Chang, H. R.; Li, Q. X.; Kim, J. H. J. Agric. Food Chem. 2007, 55, 5416.

[34] Bao, H. J.; Fang, S.; Liu, Z. J.; Shi, H. Y.; Ye, Y. H.; Wang, M. H. J. Agric. Food Chem. 2010, 58, 8167.

[35] Brown, R. W.; J. Agric. Food Chem. 1990, 38, 269.

[36] Pews, R. G.; Jackson, L. A.; Carson, C. M. US 4894085, 1990 [Chem. Abstr. 1990, 113, 152054].

[37] Sakata, G.; Makino, K.; Kusano, K.; Satow, J.; Ikai, T.; Suzuki, K. J. Pestic. Sci. (Tokyo, Jpn.) 1985, 10, 61.

[38] Fan, Z. P.; Hua, Z.; Frank, V. US 20050240049, 2005 [Chem. Abstr. 2005, 143, 422130].

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