R. Galeazzi et al., The cleavage of sulfonylurea herbicide rimsulfuron (R) under basic conditions: A computational investigation, HETEROCYCLE, 53(11), 2000, pp. 2517
By treatment at pH 9.5, starting from sulfonylurea (If) (Rimsulfuron(R)), t
he diheteroaryl amine (3) is exclusively obtained, whereas under the same c
onditions sulfonylureas (la-e) showed only cleavage of the SO2-NH bond. A r
eaction mechanism proceeding through a five-membered transition state was s
trongly suggested by both semiempirical and ab initio molecular orbital cal
culations.