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Design, synthesis and structure–activity relationship of novel oxime ether strobilurin derivatives containing substituted benzofurans

Authors

  • Ya-Qiang Xie,

    1. Department of Chemical and Biochemical Engineering, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, China
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  • Yi-Bing Huang,

    1. Department of Chemical and Biochemical Engineering, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, China
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  • Jian-She Liu,

    1. Department of Chemical and Biochemical Engineering, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, China
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  • Li-Yi Ye,

    1. Department of Chemical and Biochemical Engineering, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, China
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  • Li-Ming Che,

    1. Department of Chemical and Biochemical Engineering, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, China
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  • Song Tu,

    Corresponding author
    1. Department of Chemical and Biochemical Engineering, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, China
    • Correspondence to: Song Tu, Department of Chemical and Biochemical Engineering, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005. China. E-mail: tusong@xmu.edu.cn and Chang-Ling Liu, Shenyang Research Institute of Chemical Industry, Shenyang 110021, PR China. E-mail: liuchangling@vip.163.com

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  • Chang-Ling Liu

    Corresponding author
    1. Shenyang Research Institute of the Chemical Industry, Shenyang, China
    • Correspondence to: Song Tu, Department of Chemical and Biochemical Engineering, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005. China. E-mail: tusong@xmu.edu.cn and Chang-Ling Liu, Shenyang Research Institute of Chemical Industry, Shenyang 110021, PR China. E-mail: liuchangling@vip.163.com

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Abstract

BACKGROUND

Strobilurins are one of the most important classes of agricultural fungicides. To discover new strobilurin analogues with broad spectrum and high activity, a series of novel oxime ether strobilurin derivatives containing substituted benzofurans in the side chain were synthesised and bioassayed.

RESULTS

The synthesised compounds were characterised by 1H NMR, 13C NMR, MS and HRMS. Bioassays demonstrated that most target compounds possessed good or excellent fungicidal activities, especially against Erysiphe graminis and Pyricularia oryzae. Furthermore, methyl 3-methoxypropenoate oxime ethers exhibited remarkably higher activities against E. graminis, Colletotrichum lagenarium and Puccinia sorghi Schw. Notably, (E,E)-methyl 3-methoxy-2-{2-[({[5-fluoro-1-(benzofuran-2-yl)ethylidene]amino}oxy)methyl]phenyl}propenoate (BSF2) and (E,E)-methyl 3-methoxy-2-{2-[({[5-chloro-1-(benzofuran-2-yl)ethylidene]amino}oxy)methyl]phenyl}propenoate (BSF3) were identified as the most promising candidates for further study.

CONCLUSION

The present work demonstrates that oxime ether strobilurin derivatives containing benzofurans can be used as possible lead compounds for developing novel fungicides. © 2014 Society of Chemical Industry

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