Synthesis and biological evaluation of novel phosphonyl thiazolo pyrazoles

Abstract

A series of novel dimethyl 7-((2S,3S)-3-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-3,6-dihydro-2H-pyran-2-yl)-4-(4-fluorophenyl)-9-oxo-8-phenyl-6-thia-1,2,8-triazaspiro[4.4]non-2-en-3-ylphosphonate 11a-g were synthesized by the reaction of chalcone derivatives of (E)-5-benzylidene-2-((2S,3S)-3-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-3,6-dihydro-2H-pyran-2-yl)-3-phenylthiazolidin-4-one 10a-g with Bestmann-Ohira reagent. The chemical structures of newly synthesized compounds were elucidated by IR, NMR, MS, and elemental analysis. The compounds 11a-g were evaluated for their nematicidal activity against Dietylenchus myceliophagus and Caenorhabditis elegans, and compounds 11b, 11c, 11g, and 11f showed appreciable nematicidal activity.