Copper(II) complexes of imidazolinone herbicides

The copper(II) complexes formed by the imidazolinone herbicide Imazapyr or (+/-)-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-nicotinic acid (H(2)imz) are described. The compounds isolated in the solid state confirm that Imazapyr is a versatile bipy-like ligand able to chelate the metal ion through two different donor sets. The pair of pyridine and imidazole nitrogen atoms is bound to copper in [Cu(Himz)(2)] and [Cu(Himz)(2)(H2O)]. In these, a five-coordination at the metal ion and a geometry close to the trigonal bipyramid are favoured. The weak carboxylate group does not play a primary role in the complex formation properties of Imazapyr. However, its involvement yields the polymetallic compounds [Cu(Himz)(2)] and [Cu-3(Himz)(4)(H2O)(4)](NO3)(2). The deprotonation of the lactam group provides Imazapyr with a stronger donor set, the lactam and the pyridine nitrogens, yielding 1:1 polymeric complexes [Cu(imz)(H2O)] and [Cu(imz)(H2O)(3)]. H2O. With the methyl ester of Imazapyr (HimzOMe), the different charge of the ligand deprotonated at the lactam group allows a bis-chelated complex [Cu(imzOMe)(2)(H2O)]. H2O in which the metal ion adopts a five-coordination. Analogies have been established between the complexes of H(2)imz, HimzOMe and 2,2'-bipyridine.