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

Kai Chen1,2, Guangke He1,2, Qi Liu1,2, Hongjun Zhu1,2,*, Yufeng Li1,2 and Jueping Ni1,2

1Department 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

2Jiangsu Pesticide Research Institute Co Ltd., Nanjing 210047, P.R. China

*Corresponding author: Tel./Fax: +86 25 83172358; E-mail: zhuhj@njtech.edu.cn

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.

Reference (18)
   View Article PDF File Under a Creative Commons License