Synthesis and Insecticidal Activities of Novel Sulfur(oxygen) Con-taining Oxime Ethers as well as Structure Activity Relationship

Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (10): 1772-1779. Previous Articles Next Articles

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新型含硫(氧)肟醚衍生物的合成、杀虫活性及其结构活性关系研究

柳爱平*,a,b 王晓光a 欧晓明a 刘曙东a
莫洪波a,c 刘兴平a 王婷瑾a,b 何海军a,c
胡礼a 黄明智a 刘钊杰b 姚建仁b,d

(a湖南化工研究院国家农药创制工程技术研究中心长沙 410007)
(b华中师范大学有机合成研究所武汉 430079)
(c湖南师范大学化学化工学院长沙 410081)
(d中国农科院植物保护研究所北京 100094)

收稿日期:2007-03-11 修回日期:2008-04-01 发布日期:2008-10-20
通讯作者: 柳爱平

Synthesis and Insecticidal Activities of Novel Sulfur(oxygen) Con-taining Oxime Ethers as well as Structure Activity Relationship

LIU, Ai-Ping*,a,b WANG, Xiao-Guanga OU, Xiao-Minga LIU, Shu-Donga
MO, Hong-Boa,c LIU, Xin-Pinga WANG, Ting-Jina,b HE, Hai-Juna,c
HU, Lia HUANG, Ming-Zhia LIU, Zhao-Jieb YAO, Jian-Renb,d

(a National Engineering Research Center for Agrochemicals, Hunan Research Institute of
Chemical Industry, Changsha 410007)
(b Institute of Organic Synthesis, Central China Normal University, Wuhan 430079)
(c College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081)
(d Institute of Plant Protection, China Academy of Agricultural Sciences, Beijing 100094)

Received:2007-03-11 Revised:2008-04-01 Published:2008-10-20
Contact: LIU, Ai-Ping

Abstract

96 novel sulfur(oxygen) containing 1-aryl O-benzyl oximes were synthesized by the reaction of sulfur(oxygen) containing 1-aryl oximes with the corresponding halides of pyrethriod alcohols in the pres-ence of sodium hydroxide and phase transfer catalyst or with triethylquaternary ammonium salts of halides of pyrethriod alcohol in the presence of sodium hydroxide. The title compounds were identified by MS, 1H NMR, IR spectra and elemental analyses. Bioassay showed that these compounds showed remarkable insec-ticidal activities against homopteran and lepidopteran pests. C74 and C93 showed a medial effective dose [LC50/(mg• L－1)] of 1.4, 0.63 and 0.31, 1.2 against oriental army worm and leafhopper respectively, the LC50 values of compounds C74 and C93 were better than that of the commercialized insecticide fenvalerate.

Key words: insecticidal activity, sulfur(oxygen) containing oxime ether, homoptera, lepidoptera

Cite this article

LIU, Ai-Ping*,a,b WANG, Xiao-Guanga OU, Xiao-Minga LIU, Shu-Donga
MO, Hong-Boa,c LIU, Xin-Pinga WANG, Ting-Jina,b HE, Hai-Juna,c
HU, Lia HUANG, Ming-Zhia LIU, Zhao-Jieb YAO, Jian-Renb,d

. Synthesis and Insecticidal Activities of Novel Sulfur(oxygen) Con-taining Oxime Ethers as well as Structure Activity Relationship[J]. Chin. J. Org. Chem., 2008, 28(10): 1772-1779.

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新型含硫(氧)肟醚衍生物的合成、杀虫活性及其结构活性关系研究

Synthesis and Insecticidal Activities of Novel Sulfur(oxygen) Con-taining Oxime Ethers as well as Structure Activity Relationship

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