Design, synthesis, and biological evaluation of novel pyrethrin derivatives containing 1,3,4-oxadiazole and thioether moieties as active insecticidal agents

被引：16

作者：

Yang, Zaibo ^{[1
]}

Li, Pei ^{[1
,2
,3
]}

He, Yinju ^{[1
]}

Luo, Jun ^{[1
]}

Zhou, Jing ^{[1
]}

Wu, Yinghong ^{[1
]}

Chen, Liantao ^{[1
]}

机构：

[1] Qiannan Normal Univ Nationalities, Sch Chem & Chem Engn, Duyun 558000, Peoples R China

[2] Kaili Univ, Qiandongnan Engn & Technol Res Ctr Comprehens Uti, Kaili 556011, Peoples R China

[3] Kaili Univ, Qiandongnan Tradit Med Res & Dev Ctr, Kaili 556011, Peoples R China

来源：

CHEMICAL PAPERS | 2020年 / 74卷 / 05期

基金：

中国国家自然科学基金;

关键词：

Pyrethrin; trans-Ethyl chrysanthemate; 1; 3; 4-Oxadiazole; Thioether; Insecticidal activity; 1,3,4-THIADIAZOLE; BIOACTIVITIES;

D O I：

10.1007/s11696-019-01012-4

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

To discover and develop novel active molecules, in this study, a series of novel pyrethrin derivatives containing 1,3,4-oxadiazole and thioether moieties were designed and synthesized. Bioassay results revealed that some of the target compounds possessed good insecticidal activities against Plutella xylostella (P. xylostella), Vegetable aphids (V. aphids), and Empoasca vitis (E. vitis), respectively, which were even better than those of the commercial insecticidal agents chlorpyrifos, beta cypermethrin, spinosad, and azadirachtin. The results favored our rational design intention and provide a new class of small-molecule inhibitors available for the development of active insecticidal agents targeting P. xylostella, V. aphids, and E. vitis.

引用

页码：1621 / 1632

页数：12

共 33 条

[1] Synthesis and Bioactivities of Novel 1,2,4-Triazolo[1,5-a]pyrimidine Derivatives Containing 7-(1,3,4-Oxadiazolyl)thioether Moiety
Bao, Xiaoping
Lin, Xuanfu
Jian, Junyou
Zhang, Feng
Zou, Linbo
[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2013, 33 (05) : 995 - 999
[2] PYRETHROID AND ORGANOPHOSPHATE RESISTANCE IN THE TOBACCO WHITEFLY BEMISIA-TABACI (HOMOPTERA, ALEYRODIDAE)
CAHILL, M
BYRNE, FJ
GERMAN, K
DENHOLM, I
DEVONSHIRE, AL
[J]. BULLETIN OF ENTOMOLOGICAL RESEARCH, 1995, 85 (02) : 181 - 187
[3] Casida J.E., 1995, PYRETHRUM FLOWERS PR
[4] Casida JE, 1973, PYRETHRUM NATURAL IN
[5] Synthesis, Nematicidal Evaluation, and 3D-QSAR Analysis of Novel 1,3,4-Oxadiazole-Cinnamic Acid Hybrids
Chen, Jixiang
Chen, Yongzhong
Gan, Xiuhai
Song, Baojing
Hu, Deyu
Song, Baoan
[J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2018, 66 (37) : 9616 - 9623
[6] Synthesis and Insecticidal Activities of Novel Anthranilic Diamides Containing Modified N-Pyridylpyrazoles
Feng, Qi
Liu, Zhi-Li
Xiong, Li-Xia
Wang, Ming-Zhong
Li, Yong-Qiang
Li, Zheng-Ming
[J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2010, 58 (23) : 12327 - 12336
[7] Design, synthesis, antiviral activity and three-dimensional quantitative structure-activity relationship study of novel 1,4-pentadien-3-one derivatives containing the 1,3,4-oxadiazole moiety
Gan, Xiuhai
Hu, Deyu
Li, Pei
Wu, Jian
Chen, Xuewen
Xue, Wei
Song, Baoan
[J]. PEST MANAGEMENT SCIENCE, 2016, 72 (03) : 534 - 543
[8] Semisynthesis and insecticidal activity of some novel fraxinellone-based thioethers containing 1,3,4-oxadiazole moiety
Guo, Yong
Wang, Xiaoguang
Fan, Jiangping
Zhang, Qian
Wang, Yi
Zhao, Yi
Huang, Mengxing
Ding, Ming
Zhang, Yanbing
[J]. ROYAL SOCIETY OPEN SCIENCE, 2017, 4 (12):
[9] Holan G, 1982, USP, Patent No. 4309350
[10] Synthesis of novel 1,3,4-oxadiazole derivatives and their biological properties
Husain, Asif
Ajmal, Mohammed
[J]. ACTA PHARMACEUTICA, 2009, 59 (02) : 223 - 233

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