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Design, Synthesis and Insecticidal Evaluation of Anthranilic Diamides Containing Optically Pure Amino Acid Moiety
Author(s) -
Zhou Shaa,
Zhou Sha,
Hua Xuewen,
Wei Wei,
Xie Yongtao,
Chen Minggui,
Meng Xiangde,
Liu Ming,
Xiong Lixia,
Yang Na,
Wang Baolei,
Li Zhengming
Publication year - 2016
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201600539
Subject(s) - chemistry , plutella , moiety , mythimna separata , stereochemistry , pyrazole , amino acid , serine , specific rotation , bioassay , organic chemistry , biochemistry , larva , botany , genetics , biology , enzyme
Abstract Two series of N ‐pyridylpyrazolecarboxamide derivatives were designed and synthesized by introducing D ‐alanine acid esters and D ‐serine acid esters into the skelecton of chlorantraniliprole. The obtained structures were characterized by 1 H NMR, 13 C NMR, elemental analysis and specific optical rotation analysis. Preliminary bioassays indicated that some compounds displayed excellent insecticidal activities against Mythimna separate and Plutella xylostella in comparison with chlorantraniliprole. In particular, IIq showed excellent insecticidal activity against Plutella xylostella with a mortality rate of 90% at 0.01 mg·L −1 . A 3D‐QSAR (CoMSIA) study was performed in order to disclose the insecticidal structure‐activity relationship and indicate the future work. The CoMSIA study demonstrated that large substitutes and electron deficient groups at the 3‐position of pyrazole ring are favorable, the same as a small group near the ester groups of amino acid.