REACTIONS OF 4-ARYL-1-HYDRAZINOPHTHALAZINES WITH CARBONYL-COMPOUNDS

Reaction of 1-hydrazino-4-phenylphthalazine and 4-benzyl-1-hydrazinophthalazine with different carbonyl compounds are described. With oxalic acid, the two cyclic amidrazones reacted to give 6-aryl-1,2,4-triazolo[3,4-a]phthalazines. Reaction with diethyl oxalate, however, afforded the corresponding 7-aryl-3,4-dioxo-1,2,4-triazino[3,4-a]phthalazines. With pyruvic acid, ethyl pyruvate, or methyl phenyl glyoxylate the corresponding hydrazones were obtained which were cyclized to 7-aryl-3-methyl or 7-aryl-3-phenyl-1,2,4-triazino[3,4-a]phthalazines, respectively. Whereas the reaction of the two cyclic amidrazones with acetylacetone or ethyl phenyl propiolate gave pyrazole derivatives, their reaction with ethyl acetoacetate gave 6-aryl-3-methyl-1,2,4-triazolo[3,4-a]phthalazines. The results of biological testing of representative examples of the prepared compounds as insecticides and nematicides are reported.