title: Design, synthesis, insecticidal activity and structure-activity relationship of 3,3-dichloro-2-propenyloxy-containing phthalic acid diamide structures.
abstract: 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.
  
  
  CONCLUSIONS
  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.
authors.affiliation: Department of Applied Chemistry, Nanjing University of Technology, Nanjing, People's Republic of China.
authors.forename: Mei-Li
authors.initials: ML
authors.lastname: Feng
authors.forename: Yu-Feng
authors.initials: YF
authors.lastname: Li
authors.forename: Hong-Jun
authors.initials: HJ
authors.lastname: Zhu
authors.forename: Jue-Ping
authors.initials: JP
authors.lastname: Ni
authors.forename: Bin-Bin
authors.initials: BB
authors.lastname: Xi
authors.forename: Liang
authors.initials: L
authors.lastname: Zhao
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D060326:Chemistry Techniques, Synthetic; D018360:Crystallography, X-Ray; D015195:Drug Design; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry; D007915:Lepidoptera; D010795:Phthalic Acids / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000577:Amides; D007306:Insecticides; D010795:Phthalic Acids; C032279:phthalic acid