Identification and Characterization of the Isomeric Impurity of the Fungicide "Cyazofamid".
Jyoti KannoujiaDevendra NagineniRamesh RoddaRamesh ChilukuriJagadeesh Babu NanuboluParameswari AkshinthalaSoujanya YarasiSrinivas KantevariPrabhakar SripadiPublished in: Chemistry, an Asian journal (2023)
Identification and characterization of biproducts/ impurities present in agrochemicals are critical in view of their efficacy and safety towards public health. We herein present our study on identification and characterization of an impurity, 5-chloro-2-cyano-N,N-dimethyl-4-p-tolylimidazole-1-sulfonamide (2) present in the fungicide, "cyazofamid". Intermittent HPLC analysis of the reaction of substituted imidazole (1) with N,N-dimethylsulfamoyl chloride suggested that 2 is formed during the reaction. Isolation by preparative HPLC and characterization by NMR, LC/HRMS, MS/MS and single crystal XRD analysis confirmed 2 as an isomer of cyazofamid, wherein the N,N-dimethyl sulfonamide group was positioned on the other nitrogen of imidazole in close proximity to chloride group. Computational studies further supported the formation of 2 and ruled out the other possible isomeric structures.
Keyphrases
- ms ms
- simultaneous determination
- public health
- liquid chromatography tandem mass spectrometry
- high resolution
- high performance liquid chromatography
- solid phase extraction
- magnetic resonance
- tandem mass spectrometry
- solid state
- liquid chromatography
- high resolution mass spectrometry
- high intensity
- molecular docking
- molecular dynamics simulations