New phosphorus-nitrogen compounds: synthesis, spectroscopiccharacterization and fungicide studies

The phosphorus-nitrogen compounds, such as phosphoramides and thiophosphoramides werestudied in viewpoint of their agrochemical delivery [۱-۴]. In the presence work, new phosphorusnitrogencompounds were synthesized and used for the study of antifungal properties. Thecompounds, including (R)-[(۲,۳-F۲)C۶H۳C(O)NH]P(O)[NHCH(CH۳)C۶H۵]۲ (۱), (S)-[(۲,۳-F۲)C۶H۳C(O)NH]P(O)[NHCH(CH۳)C۶H۵]۲ (۲), and P[S][NHCH۲C۶H۴-۴-F]۳ (۳) were used in thisstudy. Characterization was done by CHN analysis, Mass, IR and NMR spectroscopy. The ۳۱Psignals are revealed at ۴.۰۱ and ۴.۱۰ ppm for the phosphoramides ۱ and ۲, respectively and at۶۵.۴۰ ppm for the thiophosphoramide ۳. In the ۱H NMR experiment, the broad signals at ۹.۴۲ ppmfor ۱ and ۹.۲۶ ppm for ۲ associate to the NCP—H unit (NCP is the nitrogen atom of the C(O)NHP(O)segment), and the two other N—H protons appear as pseudo triplets at ۴.۸۸ and ۵.۰۶ ppm for ۱and ۴.۹۱ and ۵.۰۶ ppm for ۲. For compound ۳, the NH signal appears as a multiplet at ۴.۸۲ ppm.The ۱۹F signals of compounds ۱ and ۲ are revealed as doublets at –۱۳۸.۵۲ and –۱۴۰.۲۶ ppm for ۱and –۱۳۸.۵۱ and –۱۴۰.۲۶ ppm for ۲. For ۳, the fluorine signal appears at –۱۱۶.۷۳ ppm. Theantifungal properties of these compounds against phytopathogenic fungi such as Rhizoctoniasolani and Fusarium culmorum were studied, which showed their effectiveness against both fungi.

Keywords:

phosphorus-nitrogen compounds , NMR spectroscopy , antifungal properties , phytopathogenic fungi.