Synthesis of Halopyrazole Matrine Derivatives and Their Insecticidal and Fungicidal Activities

Molecules. 2022 Aug 5;27(15):4974. doi: 10.3390/molecules27154974.

Abstract

Matrine is a traditional botanical pesticide with a broad-spectrum biological activity that is widely applied in agriculture. Halopyrazole groups are successfully introduced to the C13 of matrine to synthesize eight new derivatives with a yield of 78-87%. The insecticidal activity results show that the introduction of halopyrazole groups can significantly improve the insecticidal activity of matrine on Plutella xylostella, Mythimna separata and Spodoptera frugiperda with a corrected mortality rate of 100%, which is 25-65% higher than matrine. The fungicidal activity results indicate that derivatives have a high inhibitory effect on Ceratobasidium cornigerum, Cibberella sanbinetti, Gibberrlla zeae and Collectot tichum gloeosporioides. Thereinto, 4-Cl-Pyr-Mat has the best result, with an inhibition rate of 23-33% higher than that of matrine. Therefore, the introduction of halogenated pyrazole groups can improve the agricultural activity of matrine.

Keywords: fungicidal activity; insecticidal activity; matrine derivatives; structural modification.

MeSH terms

  • Alkaloids
  • Animals
  • Insecticides* / pharmacology
  • Matrines
  • Molecular Structure
  • Moths*
  • Quinolizines / pharmacology
  • Structure-Activity Relationship

Substances

  • Alkaloids
  • Insecticides
  • Quinolizines
  • Matrines