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Design, synthesis, insecticidal activity and structure–activity relationship of 3,3‐dichloro‐2‐propenyloxy‐containing phthalic acid diamide structures
Author(s) -
Feng MeiLi,
Li YuFeng,
Zhu HongJun,
Ni JuePing,
Xi BinBin,
Zhao Liang
Publication year - 2012
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.3243
Subject(s) - phthalic acid , substituent , plutella , chemistry , amide , aniline , ring (chemistry) , trifluoromethyl , phthalic anhydride , chemical structure , stereochemistry , structure–activity relationship , organic chemistry , biology , in vitro , catalysis , biochemistry , ecology , lepidoptera genitalia , alkyl
BACKGROUND: 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. RESULTS: 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. CONCLUSION: 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 relationships with the parent structure provided information that could direct further investigation on structure modification. Copyright © 2012 Society of Chemical Industry