Synthesis of a new class of pyridine herbicide

A new class of fluoroalkylated pyridine herbicides has been discovered. The 3,5-pyridinedicarboxylates are prepared either from ethyl 4,4,4-trifluoroacetoacetate via Hantzsch dihydropyridine synthesis or from trifluoroacetonitrile via cyclocondensation and carboxylation. Hydrolysis of the ester groups, followed by derivatization of the resulting acids yields a variety of herbicidally active analogs including ester, thioester, amide, halogen, amino, alkoxy and alkylthio derivatives.