138724-53-5Relevant articles and documents
Adsorption and degradation of rimsulfuron on Al hectorite
Pantani, Ottorino,Pusino, Alba,Calamai, Luca,Gessa, Carlo,Fusi, Paolo
, p. 617 - 621 (1996)
A study was carried out to examine the interactions between a smectite (hectorite) saturated with Al3+ and a sulfonylurea herbicide, rimsulfuron [N-((4,6-dimethoxypyrimidin-2-yl)aminocarbonyl)-3-(ethylsulfonyl)-2- pyridinesulfonamide]. As rimsulfuron is extremely unstable in water, to evaluate the role of the clay surface in decomposing the herbicide, the experiments were carried out in chloroform solution. The coordination of the C=O group is initially involved in the adsorption as revealed by FT-IR analysis. The adsorbed rimsulfuron decomposes initially into N-(4,6 dimethoxypyrimidin-2-yl)-N-((3-(ethylsulfonyl)-2-pyridinyl)urea (metabolite 367). This metabolite is adsorbed onto a clay surface by coordination of the C=O group and protonation of the pyrimidine ring. Successively, this metabolite decomposes on a clay surface to N-[(3-ethylsulfonyl)-2-pyridinyl]-4,6-dimethoxy-2-pyrimidineamine (metabolite 324). This second metabolite remains adsorbed by protonation of its pyrimidine ring.
Intramolecular and bimolecular nucleophilic substitutions of rimsulfuron sulfonylurea
Rouchaud, J.,Neus, O.,Moulard, C.
, p. 59 - 66 (2007/10/03)
The sulfonylurea herbicide rimsulfuron 1 (N-((4,6-dimethoxypyrimidin-2-yl)aminocarbonyl)-3-(ethylsulfonyl)-2-pyridinesulfonamide) in aqueous solutions of KOH, NaOH, NH4OH, or dilute HCl, and thermally (rimsulfuron or monomethylated rimsulfuron at the sulfonamide hydrogen) was transformed by SO2 extrusion and intramolecular nucleophilic substitution into 2-(N-(4,6-dimethoxy)pyrimidin-2-yl)amino-3-ethylsulfonylpyridine 3.In mild methanol + HCl conditions, the intermediate rearranged urea N-(4,6-dimethoxypyrimidin-2-yl)-N-(3-(ethylsulfonyl)-2-pyridinyl)urea 2 was isolated.In concentrated hydrochloric acid, rimsulfuron 1 was transformed by bimolecular nucleophilic substitution successively into 2-chloro-3-ethylsulfonylpyridine 6 and 2-hydroxy-3-ethylsulfonylpyridine 4.Sodium sulfite transformed rimsulfuron 1 into a mixture of 2-sodiumsulfonate-3-ethylsulfonylpyridine 7 and amine 3.