Nature of N-S bond cleavage of 2,3-dihydro-2,2-dimethyl-7-benzofuranyl (di-n-butylaminosulfenyl) (methyl)carbamate.
The cleavage of the N-S bond in 2,3-dihydro-2,2-dimethyl-7-benzofuranyl (di-n-butylaminosulfenyl) (methyl)carbamate was examined in different buffer solutions (hydrolysis), in buffer solution containing sulfhydryl reagents (thiolysis) and on thin-layer chromatographic plates. In buffer solution and on thin-layer plates, N-S bond cleavage readily occurred to give carbofuran as a major product, with minor amounts of bis-carbofuran-N,N'-disulfide and -trisulfide. The hydrolysis reaction in buffer proceeded with first-order kinetics. Significant amounts of an unknown polar compound were obtained in buffer solution and on thin-layer plates. In the presence of excess cysteine and glutathione at pH 7.0, thiolytic N-S bond cleavage occurred with first-order kinetics to give carbofuran as the sole identifiable product. At pH 5.0, three minor products were obtained along with carbofuran.
D002021:Buffers; D002235:Carbofuran / Q000031:analogs & derivatives; D055598:Chemical Phenomena; D002621:Chemistry; D002855:Chromatography, Thin Layer; D006868:Hydrolysis; D007306:Insecticides / Q000031:analogs & derivatives; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D009584:Nitrogen; D013438:Sulfhydryl Compounds; D013455:Sulfur
D002021:Buffers; D007306:Insecticides; D013438:Sulfhydryl Compounds; C023612:dibutylaminosulfenylcarbofuran; D013455:Sulfur; D009584:Nitrogen; D002235:Carbofuran