title: Structure-based bioisosterism design, synthesis, insecticidal activity and structure-activity relationship (SAR) of anthranilic diamide analogues containing 1,2,4-oxadiazole rings.
abstract: BACKGROUND
  Anthranilic diamide derivatives are among the most important classes of synthetic insecticides. Moreover, the 1,2,4-oxadiazole heterocycle, a bioisostere of amide, has been extensively used in pesticides. In order to discover novel molecules with high insecticidal activities, a series of anthranilic diamide analogues containing 1,2,4-oxadiazole rings were designed and synthesised.
  
  
  RESULTS
  A series of novel anthranilic diamide derivatives containing 1,2,4-oxadiazole were obtained, and confirmed by1H and13C nuclear magnetic resonance and high-resolution mass spectrometry. The structure of 3-bromo-N-(4-chloro-2-methyl-6-{3-[(methylsulphonyl)methyl]-1,2,4-oxadiazol-5-yl}phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide was further characterised by X-ray diffraction analysis. In addition, bioassays showed that most of the newly synthesised compounds displayed 100% mortality against Plutella xylostella at 100 mg L-1, and compound 3IIl showed 90% larvicidal activities at a concentration of 0.5 mg L-1. The LC50value of 3IIl was 0.20 mg L-1, which indicated that it may be used as a potential leading compound for further structural optimisation. Furthermore, brief comparative molecular field analysis (CoMFA) models were established to study the structure-activity relationships (SARs) of the title compounds.
  
  
  CONCLUSIONS
  Compound 3IIl may be used as a potential leading compound for further structural optimisation, and SARs and CoMFA models could provide reliable clues for further structural optimisation. © 2016 Society of Chemical Industry.
authors.affiliation: Department of Applied Chemistry, College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing, China.
authors.forename: Qi
authors.initials: Q
authors.lastname: Liu
authors.affiliation: Department of Applied Chemistry, College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing, China.
authors.forename: Rui
authors.initials: R
authors.lastname: Zhu
authors.affiliation: Department of Applied Chemistry, College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing, China.
authors.forename: Shang
authors.initials: S
authors.lastname: Gao
authors.affiliation: Department of Applied Chemistry, College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing, China.
authors.forename: Shi-Han
authors.initials: SH
authors.lastname: Ma
authors.affiliation: Department of Applied Chemistry, College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing, China.
authors.forename: Hai-Jun
authors.initials: HJ
authors.lastname: Tang
authors.affiliation: Department of Applied Chemistry, College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing, China.
authors.forename: Jian-Jun
authors.initials: JJ
authors.lastname: Yang
authors.affiliation: Jiangsu Pesticide Research Institute Co Ltd, Nanjing, China.
authors.forename: Ya-Mei
authors.initials: YM
authors.lastname: Diao
authors.affiliation: Jiangsu Pesticide Research Institute Co Ltd, Nanjing, China.
authors.forename: Hong-Lei
authors.initials: HL
authors.lastname: Wang
authors.affiliation: Department of Applied Chemistry, College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing, China.
authors.forename: Hong-Jun
authors.initials: HJ
authors.lastname: Zhu
mesh_terms: D000818:Animals; D060326:Chemistry Techniques, Synthetic; D003958:Diamide / Q000138:chemical synthesis* / Q000737:chemistry*; D015195:Drug Design; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry*; D007555:Isoxazoles / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D009036:Moths; D010069:Oxadiazoles / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D007306:Insecticides; D007555:Isoxazoles; D010069:Oxadiazoles; D003958:Diamide; C033962:anthranil
keywords: 1,2,4-oxadiazole; CoMFA model; anthranilic diamides; insecticidal activity; structure-based bioisosterism