Design, synthesis, insecticidal activity and structure-activity relationship of 3,3-dichloro-2-propenyloxy-containing phthalic acid diamide structures

Pest Management Science
Mei-Li FengLiang Zhao

Abstract

Phthalic acid diamide derivatives are among the most important classes of synthetic insecticides. In this study, a 3,3-dichloro-2-propenyloxy group, the essential active group of pyridalyl derivatives, was incorporated into phthalic acid diamide derivatives with the aim of combining the active groups to generate more potent insecticides. Thirty-one new phthalic acid diamides were obtained, and these were characterised by (1) H and (13) C NMR. The structure of N(2) -[1,1-dimethyl-2-(methoxy)ethyl]-3-iodo-N(1) -[4-(3,3-dichloro-2-propenyloxy)-3-(trifluoromethyl)phenyl]-1,2-benzenedicarboxamide was determined by X-ray diffraction crystallography. The insecticidal activities of the compounds against Plutella xylostella were evaluated. The title compounds exhibited excellent larvicidal activities against P. xylostella. Structure-activity relationships revealed that varying the combination of aliphatic amide and aromatic amide moieties, or the nature and position of substituent Y on the aniline ring, could aid the design of structures with superior performance. A series of novel phthalic acid diamides containing a 3,3-dichloro-2-propenyloxy group at the 4-position of the aniline ring were designed and synthesised. Structure-activity ...Continue Reading

References

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Citations

Dec 17, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Hong DaiYujun Shi
May 13, 2014·Pest Management Science·Jun LiGuang-Fu Yang
Jun 3, 2020·Annals of the New York Academy of Sciences·Min LiaoShangzhong Liu

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