Synthesis, Insecticidal Activities, and Structure-Activity Relationship of Phenylpyrazole Derivatives Containing a Fluoro-Substituted Benzene Moiety

被引：30

作者：

Zhao, Yangyang ^{[1
]}

Gao, Li ^{[1
]}

Li, Huangong ^{[1
]}

Sun, Pengwei ^{[1
]}

Meng, Fanfei ^{[1
]}

Zhang, Yan ^{[1
]}

Xie, Yongtao ^{[2
]}

Sun, Binqiao ^{[1
]}

Zhou, Sha ^{[1
]}

Ma, Yi ^{[1
]}

Xiong, Lixia ^{[1
]}

Yang, Na ^{[1
]}

Li, Yuxin ^{[1
]}

Li, Zhengming ^{[1
]}

机构：

[1] Nankai Univ, Inst Elementoorgan Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

[2] Nanyang Technol Univ NTU, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY | 2020年 / 68卷 / 40期

基金：

中国国家自然科学基金;

关键词：

insecticidal activity; fluorine substitution; phenylpyrazole; electrophysiology study; SAR; ANTHRANILIC DIAMIDES; BIOLOGICAL-ACTIVITIES; PESTICIDE-RESIDUES; SAR;

D O I：

10.1021/acs.jafc.9b08090

中图分类号：

S [农业科学];

学科分类号：

09 ;

摘要：

Fluorinated organic compounds represent a growing and important family of commercial chemicals. Introduction of fluorine into active ingredients has become an effective way to develop modern crop protection products. Given the particular properties of fluorine and high efficiency and selectivity of diamide insecticides, we designed and synthesized 27 anthranilic diamides analogues containing fluoro-sustituted phenylpyrazole. A preliminary bioassay indicated that most target compounds exhibited good biological activity against Mythimna separata and Plutella xylostella. Compound IIIf containing a 2,4,6-trifluoro-substituted benzene ring showed 43% insecticidal activity against M. separata at 0.1 mg L-1, while the control chlorantraniliprole was 36%. The activity of IIIe against P. xylostella at 10(-5) mg L-1 was 94%, compared with that of the control being 70%. Thus, introduction of fluorine into diamide insecticides was useful for increasing activity. Insect electrophysiology studies showed that the calcium concentration in the nerve cells of third M. separata larvae was elevated by IIIf, which further confirmed that ryanodine receptor (RyR) was its potential target.

引用

页码：11282 / 11289

页数：8

共 36 条

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