Design, synthesis, and biological activity of oxime ether strobilurin derivatives containing indole moiety as novel fungicide

Chem Biol Drug Des. 2015 Jun;85(6):743-55. doi: 10.1111/cbdd.12460. Epub 2014 Nov 15.

Abstract

Twenty-one novel oxime ether strobilurins containing indole moiety, which employed an indole group to stabilize the E-styryl group in Enoxastrobin, were designed and synthesized. The biological assay indicated that most compounds exhibited potent fungicidal activities. The structure-activity relationship study demonstrated that the synthesized methyl 3-methoxypropenoate oxime ethers 7b-e exhibited remarkably high activities among all the synthesized oxime ether compounds 7. Moreover, the fungicidal activities of methyl α-(methoxyimino)benzeneacetate oxime ethers compounds 7f-i and N-methoxy-carbamic acid methyl esters compounds 7j-m showed significant differences compared to the corresponding products of ammonolysis.

Keywords: fungicidal activities; fungicide; indole; oxime ether; strobilurins.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ethers / chemical synthesis
  • Ethers / chemistry
  • Ethers / pharmacology
  • Fatty Acids, Unsaturated / chemical synthesis
  • Fatty Acids, Unsaturated / chemistry
  • Fatty Acids, Unsaturated / pharmacology
  • Fungi / drug effects*
  • Fungicides, Industrial / chemical synthesis
  • Fungicides, Industrial / chemistry*
  • Fungicides, Industrial / pharmacology
  • Indoles / chemical synthesis
  • Indoles / chemistry*
  • Indoles / pharmacology
  • Methacrylates / chemical synthesis
  • Methacrylates / chemistry
  • Methacrylates / pharmacology
  • Oximes / chemical synthesis
  • Oximes / chemistry*
  • Oximes / pharmacology
  • Strobilurins
  • Structure-Activity Relationship

Substances

  • Ethers
  • Fatty Acids, Unsaturated
  • Fungicides, Industrial
  • Indoles
  • Methacrylates
  • Oximes
  • Strobilurins
  • mucidin
  • indole