The cleavage of sulfonylurea herbicide rimsulfuron (R) under basic conditions: A computational investigation

Authors
Galeazzi, R Marucchini, C Orena, M Porzi, G
Citation
R. Galeazzi et al., The cleavage of sulfonylurea herbicide rimsulfuron (R) under basic conditions: A computational investigation, HETEROCYCLE, 53(11), 2000, pp. 2517
Citations number
44
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
53
Issue
11
Year of publication
2000
Database
ISI
SICI code
0385-5414(20001101)53:11<2517:TCOSHR>2.0.ZU;2-F
Abstract
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.