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Wu T.,Nanjing University of Technology | Ma H.,Jiangsu Pesticide Research Institute Co. | Tian H.,Nanjing Agricultural University | Ni J.,Jiangsu Pesticide Research Institute Co. | Yun Z.,Nanjing University of Technology
Chinese Journal of Organic Chemistry | Year: 2010

Fourteen novel 3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propyl pyrazole-5-carboxylate derivatives were synthesized by the reaction of 3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propan-l-ol with pyrazole-5-carboxylic acid derivatives, and confirmed by IR, 1H NMR techniques and elemental analysis. The preliminary bioassay showed that the compounds exhibited good activity against lepidopterous pests. Source


Feng M.-L.,Nanjing University of Technology | Li Y.-F.,Nanjing University of Technology | Zhu H.-J.,Nanjing University of Technology | Ni J.-P.,Jiangsu Pesticide Research Institute Co. | And 2 more authors.
Pest Management Science | Year: 2012

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 1H and 13C 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. © 2012 Society of Chemical Industry. Source


Feng M.-L.,Nanjing University of Technology | Li Y.-F.,Nanjing University of Technology | Zhu H.-J.,Nanjing University of Technology | Zhao L.,Nanjing University of Technology | And 2 more authors.
Journal of Agricultural and Food Chemistry | Year: 2010

Phthalic acid diamides have received considerable interest in agricultural chemistry due to a novel action mode, extremely high activity against a broad spectrum of lepidopterous insects, low acute toxicity to mammals, and environmentally benign characteristics. A series of phthalic acid diamides (4I-4IV) with the CF3 group at meta position on the aniline ring were synthesized. Their structures were characterized by 1H NMR and 13C NMR (or elemental analysis). The structure of N 2-[1,1-dimethyl-2-(methylthio)ethyl]-3-iodo-N1-[3-fluoro- 5-(trifluoromethyl)phenyl]-1,2-benzenedicarboxamide (4If) was determined by X-ray diffraction crystallography. Their insecticidal activities against Plutella xylostella were evaluated. The results show that some of the title compounds exhibit excellent larvicidal activities against P. xylostella, and improvement in larvicidal activity requires a reasonable combination of substituents in the parent structure, which provides some hints for further investigation on structure modification. © 2010 American Chemical Society. Source


Liu Q.,Nanjing University of Technology | Chen K.,Nanjing University of Technology | Wang Q.,Nanjing University of Technology | Ni J.,Jiangsu Pesticide Research Institute Co. | And 3 more authors.
RSC Advances | Year: 2014

A series of anthranilic diamides analogs (5a-x) containing 1,3,4-oxadiazole rings were synthesized and characterized by 1H NMR, 13C NMR and mass spectrometry. The structure of N-(4-chloro-2-methyl-6-(5-(thiophen-2-yl)-1,3,4-oxadiazol-2-yl)phenyl)methacrylamide (5u) was determined by X-ray diffraction crystallography. The insecticidal activities of these new compounds against diamondback moth (Plutella xylostella) were evaluated. Preliminary bioassays indicated that some of these compounds exhibited good insecticidal activities against P. xylostella, especially 3-bromo-N-(4-bromo-2-methyl-6-(5-(pyrazin-2-yl)-1,3,4-oxadiazol-2-yl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (5d), which displayed 100%, 80.95% and 57.14% activity against P. xylostella at 40 μg mL-1, 10 μg mL-1 and 4 μg mL-1, respectively. The relationship between structure and insecticidal activity was discussed. The density functional theory (DFT) studies could be helpful to understand the various insecticidal activities. This journal is © The Royal Society of Chemistry. Source


Li Y.,Nanjing University of Technology | Liu R.,Nanjing University of Technology | Yan Z.,Nanjing University of Technology | Zhang X.,Jiangsu Pesticide Research Institute Co. | Zhu H.,Nanjing University of Technology
Bulletin of the Korean Chemical Society | Year: 2010

A series of oxazolidinone-based strobilurin analogues were efficiently synthesized by the reaction of 3-(2-bromomethylphenyl) oxazolidin-2-one with 1-substituted phenyl-2H-pyrazolin-3-one. Their structures were confirmed and characterized by 1H-NMR, 13C-NMR, elemental analysis, and mass spectroscopy. In addition, the crystal structure of the target compound 3-(2-((1-phenyl-2H-pyrazol-3-yloxy)methyl)phenyl) oxazolidin-2-one was determined by single crystal X-ray diffraction. The bioassay results of these compounds indicated that some of the oxazolidin-2-one derivatives containing N-substituted phenyl 2H-pyrazol ring exhibited potential in vivo fungicidal activities against M. grisea at the dosage of 1 g L-1. Source

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