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Synthesis, insecticidal activities and structure–activity relationship studies of novel anthranilic diamides containing pyridylpyrazole‐4‐carboxamide
Author(s) -
Chen Kai,
Liu Qi,
Ni JuePing,
Zhu HongJun,
Li YuFeng,
Wang Qiang
Publication year - 2015
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/ps.3954
Subject(s) - amide , carboxamide , moiety , chemistry , anthranilic acid , stereochemistry , proton nmr , structure–activity relationship , combinatorial chemistry , organic chemistry , biochemistry , in vitro
BACKGROUND Anthranilic diamide insecticides containing pyridylpyrazole‐5‐carboxamide are extremely important in modern agriculture. New structurally modified compounds with high insecticidal activity were discovered by designing a series of novel pyridylpyrazole‐4‐carboxamides ( 9I to 9IV ) and pyridylpyrazole‐4‐carboxamides ( 10I to 10IV ), the latter designed by the cyclisation of two amides. The structure–activity relationship ( SAR ) between the two series is of interest. RESULTS Two series of novel anthranilic diamides containing pyridylpyrazole‐4‐carboxamide were synthesised and characterised via melting point, 1 H NMR , 13 C NMR , MS and elemental analyses. The insecticidal activities of these compounds against Plutella xylostella were evaluated. At a concentration of 100 mg L −1 , the compounds with unmodified amide moieties ( 9I to 9IV ) exhibited much better larvicidal activities than the other derivative compounds ( 10I to 10IV ). Most of the compounds 9I to 9IV showed over 90% larvicidal activity at 100 mg L −1 . Furthermore, compounds 9IIIa , 9IIIc , 9IIId and 9IVd displayed significant insecticidal activity at 10 mg L −1 . Density functional theory ( DFT ) calculation was carried out to provide more information regarding SAR . CONCLUSION Thirty‐two new anthranlic diamides containing pyridylpyrazole‐4‐carboxamide were designed and obtained. SAR analysis and DFT calculation results revealed that the amide moiety had a very important effect on bioactivity. This work has provided information that could aid investigations of novel insecticides. © 2014 Society of Chemical Industry