Herbicidal Activity of IK

0-diaIkyl l-(l-phenyl-l,2,4-triazol-3-yloxyacetoxy)alkylphosphonates IK including 7 compounds were synthesized by the reaction of sodium salt of l-phenyl-3-hydroxy-l,2,4-triazole M7 with l-(chloioacetoxy)aIkylphosphonates M3 using tetra-butylammonium bromide as a catalyst in acetonitrile. 

All of IK showed very weak inhibitory activity ( 20 % inhibition) against barnyard grass, crab grass, rape, setose thistle, cucumber, and lettuce for preemergence and post-emergence applications. It is noteworthy that there is no substituent on the benzene ring of l-phenyl-3-hydroxy-l,2,4-triazole moiety in IK. 

Baillie AC, Wright K, Wright BJ et al (1988) Inhibitors of pyruvate dehydrogenase as herbicides. Pestic Biochem Physiol 30 103-112 

Brienne M, Jacques J, Brianso M et al (1978) Sterochemistry of rearrangement of 1-hydroxy-2,2,2-trichlorodialkyl ethylphosphonates in 2,2-dichlorovinyl phosphates and dialkyl phosphates. Nouv J Chim 2 19-20 

Kharasch MS, Mosher RA, Bengelsdorf IS (1960) Organophosphorus chemistry addition reactions of diethyl phosphonate and the oxidation of triethyl phosphite. J Org Chem 25 1000-1006 

---