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Design, synthesis and insecticidal evaluation of novel N-pyridylpyrazolecarboxamide derivatives containing isoxazole, isoxazoline and 1,3,4-thiadiazole rings

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Chemical Research in Chinese Universities Aims and scope

Abstract

With the introduction of various heterocyclic rings at the benzene part of anthranilic diamides, a series of N-pyridylpyrazolecarboxamide derivatives containing isoxazole, isoxazoline and 1,3,4-thiadiazole rings was designed, synthesized and evaluated for their insecticidal activities. The structures of the obtained novel target compounds were confirmed by means of 1H NMR, 13C NMR and HRMS. The bioassay results indicated that most of the target compounds displayed moderate or good insecticidal activities against oriental armyworm and diamondback moth at the adopted concentrations compared with chlorantraniliprole, especially compounds Ii and Il, of which the LC50 and LC95 values against oriental armyworm were further measured. The structure-activity relationship demonstrated that the introduction of chlorine in benzene ring, bromomethyl and acetoxyl substituents in 4,5-dihydroisoxazole part was more advantageous to improve the corresponding insecticidal activities than the introduction of other substituents and heterocycles.

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Authors and Affiliations

  1. College of Agronomy, Liaocheng University, Liaocheng, 252000, P. R. China

    Xuewen Hua

  2. Patent Examination Cooperation Hubei Center of the Patent Office, SIPO, Wuhan, 430205, P. R. China

    Chen Liu

  3. State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Nankai University, Tianjin, 300071, P. R. China

    Sha Zhou, Minggui Chen, Lixia Xiong, Yongqiang Li & Zhengming Li

Authors
  1. Xuewen Hua
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  2. Chen Liu
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  3. Sha Zhou
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  4. Minggui Chen
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  5. Lixia Xiong
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  6. Yongqiang Li
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  7. Zhengming Li
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Corresponding author

Correspondence to Xuewen Hua.

Additional information

Supported by the State Key Laboratory of Elemento-Organic Chemistry and Doctoral Research Startup Foundation of Liaocheng University, China(No. 318051625).

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Hua, X., Liu, C., Zhou, S. et al. Design, synthesis and insecticidal evaluation of novel N-pyridylpyrazolecarboxamide derivatives containing isoxazole, isoxazoline and 1,3,4-thiadiazole rings. Chem. Res. Chin. Univ. 33, 882–889 (2017). https://doi.org/10.1007/s40242-017-7147-1

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  • DOI: https://doi.org/10.1007/s40242-017-7147-1

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