The cleavage of sulfonylurea herbicide Rimsulfuron® under basic conditions: A computational investigation

Roberta Galeazzi; Cesare Marucchini; Mario Orena; Gianni Porzi

The cleavage of sulfonylurea herbicide Rimsulfuron® under basic conditions: A computational investigation

Roberta Galeazzi, Cesare Marucchini, Mario Orena, Gianni Porzi

Istituto Nazionale di Riposo e Cura per Anziani V.E. II

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	2517-2526
Number of pages	10
Journal	Heterocycles
Volume	53
Issue number	11
Publication status	Published - Nov 1 2000

ASJC Scopus subject areas

Organic Chemistry

Cite this

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abstract = "By treatment at pH 9.5, starting from sulfonylurea (1f) (Rimsulfuron{\textregistered}), 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.",

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AU - Galeazzi, Roberta

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AU - Orena, Mario

AU - Porzi, Gianni

PY - 2000/11/1

Y1 - 2000/11/1

N2 - 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.

AB - 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.

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The cleavage of sulfonylurea herbicide Rimsulfuron® under basic conditions: A computational investigation

Abstract

ASJC Scopus subject areas

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