The discovery of SYP-10913 and SYP-11277: novel strobilurin acaricides

Pest Manag Sci. 2011 Sep;67(9):1141-6. doi: 10.1002/ps.2164. Epub 2011 Mar 30.

Abstract

Background: As previously reported, methyl (E)-2-[2-(2-phenylamino-6-trifluoromethylpyrimidin-4-yloxymethyl)phenyl]-3-methoxyacrylate has proven to be a new lead with highly acaricidal activity. Following on from this, in an effort to discover new strobilurin analogues with improved activity, a series of substituted pyrimidines were synthesised and bioassayed.

Results: All compounds were characterised by (1) H NMR, IR, MS and elemental analysis. Preliminary bioassays demonstrated that some of the title compounds exhibited notable control of Tetranychus cinnabarinus (Boisd.) at 1.25 mg L(-1) . The relationship between structure and acaricidal activity is discussed.

Conclusion: Two compounds of particular interest, 6j (SYP-10913) and 6k (SYP-11277), exhibited potent acaricidal activity. The acaricidal potencies of these analogues are higher than that of fluacrypyrim in greenhouse applications, and are comparable with those of commercial acaricides such as spirodiclofen and propargite in field trials.

Keywords: acaricidal activity; intermediate derivatisation method; pyrimidine; strobilurin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acaricides / chemical synthesis
  • Acaricides / chemistry
  • Acaricides / toxicity*
  • Animals
  • Drug Discovery
  • Fabaceae / parasitology
  • Female
  • Male
  • Mites / drug effects*
  • Molecular Structure
  • Plant Diseases / parasitology
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry
  • Pyrimidines / toxicity*
  • Structure-Activity Relationship

Substances

  • Acaricides
  • Pyrimidines