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Vol. 27 No. 3 (2015): Vol 27 Issue 3

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Synthesis, Insecticidal Activity and Structure-Activity Relationship of 2-(3,3-Dichloro-2-propenyloxy)phenyl-containing Phthalic Acid Diamide Derivatives

https://doi.org/10.14233/ajchem.2015.17122
Kai Chen
Department of Applied Chemistry, College of Science, Nanjing University of Technology,; Jiangsu Key Laboratory of Industrial Water Conservation and Emission Reduction, Nanjing 211816, P.R. China; Jiangsu Pesticide Research Institute Co Ltd., Nanjing 210047, P.R. China
Guangke He
Department of Applied Chemistry, College of Science, Nanjing University of Technology,; Jiangsu Key Laboratory of Industrial Water Conservation and Emission Reduction, Nanjing 211816, P.R. China; Jiangsu Pesticide Research Institute Co Ltd., Nanjing 210047, P.R. China
Qi Liu
Department of Applied Chemistry, College of Science, Nanjing University of Technology,; Jiangsu Key Laboratory of Industrial Water Conservation and Emission Reduction, Nanjing 211816, P.R. China; Jiangsu Pesticide Research Institute Co Ltd., Nanjing 210047, P.R. China
Hongjun Zhu
Department of Applied Chemistry, College of Science, Nanjing University of Technology,; Jiangsu Key Laboratory of Industrial Water Conservation and Emission Reduction, Nanjing 211816, P.R. China; Jiangsu Pesticide Research Institute Co Ltd., Nanjing 210047, P.R. China
Yufeng Li
Department of Applied Chemistry, College of Science, Nanjing University of Technology,; Jiangsu Key Laboratory of Industrial Water Conservation and Emission Reduction, Nanjing 211816, P.R. China; Jiangsu Pesticide Research Institute Co Ltd., Nanjing 210047, P.R. China
Jueping Ni
Department of Applied Chemistry, College of Science, Nanjing University of Technology,; Jiangsu Key Laboratory of Industrial Water Conservation and Emission Reduction, Nanjing 211816, P.R. China; Jiangsu Pesticide Research Institute Co Ltd., Nanjing 210047, P.R. China

Corresponding Author(s) : Hongjun Zhu

zhuhj@njtech.edu.cn

Asian Journal of Chemistry, Vol. 27 No. 3 (2015): Vol 27 Issue 3

Abstract

A series of novel 2-(3,3-dichloro-2-propenyloxy)phenyl-containing phthalic acid diamide derivatives (3I-3IV) were designed and synthesized. Their chemical structures were characterized by 1H NMR, mass spectrometry and elemental analyses. The insecticidal activities of these compounds against Plutella xylostella were evaluated at the concentration of 100 mg/L. Their insecticidal activity is effected by the substituent on the aliphatic amide moiety, which follows the trend of H (3I) > -SCH3 (3II) and -S(O)2CH3 (3IV) > -OCH3 (3III). Meanwhile, when the substituent (-CH3, -CF3, -Cl) on the aniline ring was introduced to the 3,3-dichloro-2-propenyloxy group in different positons, the meta-derivatives exhibit better insecticidal activity than the para-derivatives. Compared with the compounds bearing 3,3-dichloro-2-propenyloxy group on the 2-positon of the aniline ring, the compounds with that substituent on the 4-positon exhibit almost the same insecticidal activity trend but much better bioactivity.

Keywords

Phthalic acid diamides 3 3-Dichloro-2-propenyloxy Insecticidal activity Synthesis
Chen, K., He, G., Liu, Q., Zhu, H., Li, Y., & Ni, J. (2015). Synthesis, Insecticidal Activity and Structure-Activity Relationship of 2-(3,3-Dichloro-2-propenyloxy)phenyl-containing Phthalic Acid Diamide Derivatives. Asian Journal of Chemistry, 27(3), 827–832. https://doi.org/10.14233/ajchem.2015.17122
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