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Note | Regular issue | Vol 53, No. 11, 2000, pp.2517-2526
Published online, 1st January, 1970
DOI: 10.3987/COM-00-8986
The Cleavage of Sulfonylurea Herbicide Rimsulfuron® under Basic Conditions: A Computational Investigation

Roberta Galeazzi,* Cesare Marucchini, Mario Orena,* and Gianni Porzi

*Dipartimento di Scienze dei Materiali e della Terra, Università di Ancona, Via Brecce Bianche, I-60131 Ancona, Italy


By treatment at pH 9.5, starting from sulfonylurea (1f) (Rimsulfuron®), the diheteroaryl amine (3) is exclusively obtained, whereas under the same conditions sulfonylureas (1a-e) showed only cleavage of the SO2-NH bond. A reaction mechanism proceeding through a five-membered transition state was strongly suggested by both semiempirical and ab initio molecular orbital calculations.