Synthesis and Insecticidal Evaluation of 3,5-Dicyanopyridines Against Cotton Aphids via Microwave-Assisted Multicomponent Reactions

Chem Biodivers. 2024 Apr;21(4):e202400218. doi: 10.1002/cbdv.202400218. Epub 2024 Mar 8.

Abstract

Certain 2-amino-6-alkoxy-4-arylpyridine-3,5-dicyanide 1a-e were prepared via a straightforward process using microwave technology rather than conventional methods. This involved reaction of arylidenemalononitrile thru propanedinitrile in the occurrence of sodium alkoxide under MW. While, their positional isomer 4-amino-6-alkoxy-2-arylpyridine-3,5-dicyanide 3a-j have been separated from the reaction of aryl aldehydes with 2-aminoprop-1-ene-1,1,3-tricarbonitrile 2 in the presence of sodium alkoxide using microwave technic. Furthermore, the insecticidal properties of all synthesized compounds were observed with respect to Cotton aphid nymphs and adults. Neonicotinoid pesticides are indicated as the most effective pesticides toward aphids and many other pests. Many insecticides are discovered as novelties. As a result, several pyridine compounds were chemical method synthesized to serve as equivalents of neonicotinoids, a broad class of insecticides. With LC50 value of 0.03 mg/L, components 3g exhibit the highest insecticidal bioactivity. This work discusses how to find new chemicals that could be used as insecticidal agents in the future.

Keywords: Cotton Aphids; Cyanopyridine; Insecticidal evaluation; Regio-isomerism 2-aminoprop-1-e-1,1,3-tricarbonitrile; and SAR studies.

MeSH terms

  • Alcohols*
  • Animals
  • Aphids*
  • Insecticides* / chemistry
  • Microwaves
  • Neonicotinoids / pharmacology
  • Sodium / pharmacology

Substances

  • Insecticides
  • alkoxyl radical
  • Neonicotinoids
  • Sodium
  • Alcohols