Diamond Shamrock Corporation

Sds Biotech Corporation

Russell Buchman

Thomas A Magee

Larry J Powers

Andrew W Ho

William W Brand

Robert D Battershell

H Glenn Corkins

Louis Storace

Lawrence E Limpel

Edmond R Osgood

Arthur W Friedman

Robert E Moser

Zaven S Ariyan

James A Scozzie

William J Pyne

Russell M Bimber

Michael F DePompei

Novel heterobicyclic compounds of Formula I, processes for preparing same and pesticidal compositions and methods are described. ##STR1##

Insecticidal and nematocidal heterobicyclic hydroximinates,

Biologically active heterobicyclic hydroximidates and

Valuable pyridazinone intermediates to pharmaceutically useful compounds can be prepared in surprisingly high yields by the reaction of the corresponding monohydrazone with diketene, preferably in the presence of a basic catalyst. In an especially preferred embodiment, p,p'-dichlorobenzil monohydrazone and diketene are reacted in a xylene solvent in the presence of triethylamine to afford 4-acetyl-5,6-bis(p-chlorophenyl)-2H-pyridazin-3-one, which can then be reacted with ethylene carbonate in the presence of potassium carbonate to afford the antihypertensive agent, 4-acetyl-5,6-bis(p-chlorophenyl)-2-(2'-hydroxyethyl)-2H-pyridazine-3-one.

Synthesis of pyridazinone pharmaceutical intermediates using diketene

Compounds of the formula ##STR1## are useful antihypertensive agents.

Antihypertensive pyridazin(2H)-3-ones

A novel process of preparing ketoxime carbamate.

Method of preparing ketoxime carbamates

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Madison, OH, United States of America

Russell Buchman