Formation and Structure of Metal Azole Complexes

IRG/WP 08-30469

P D Evans, K J Schmalzl, C M Forsyth, G D Fallon, S Schmid, B Bendixen, S Heimdal

Divalent copper and zinc complexes with metal:azole ratio 1:2 were readily formed at room temperature with the fungicides tebuconazole and propiconazole. The structure of copper and zinc tebuconazole acetate and zinc cis-propiconazole chloride were examined by X-ray crystallography. In copper tebuconazole acetate, the copper atom lies on a crystallographic inversion centre and is coordinated to two triazole and two acetate ligands in a trans arrangement. The two binding tebuconazole N atoms and two close binding acetate O atoms form a square plane. The two remaining acetate O atoms have more distant interactions, thus forming an elongated octahedron around the copper atom. The coordination geometry of zinc tebuconazole acetate is tetrahedral and the metal is bound to two triazole and two acetate ligands. The geometry is distorted from regular owing to the size of the tebuconazole ligands. The butyl chains are less folded than for the copper tebuconazole complex, resulting in a more extended molecule. The coordination geometry of zinc cis-propiconazole chloride is also tetrahedral with the metal atom bonded to two triazole and two chloride ligands.

Keywords: copper, zinc, tebuconazole, propiconazole, complex, X-ray crystallography, fungicide, wood preservative

Conference: 08-05-25/29, Istanbul, Turkey

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