23575-68-0Relevant articles and documents
ORGANOPHOSPHORUS COMPOUNDS AS POTENTIAL FUNGICIDES. PART I. N-(ω-GUANIDINOALKYL)AMINOALKANEPHOSPHONIC ACIDS AND THEIR AMINOPHOSPHONIC PRECURSORS: PREPARATION, NMR SPECTROSCOPY, AND FAST ATOM BOMBARDMENT MASS SPECTROMETRY
Cameron, David G.,Hudson, Harry R.,Ojo, Isaac A. O.,Pianka, Max
, p. 183 - 198 (2007/10/02)
N-(ω-Aminoalkyl)- and N-(ω-guanidinoalkyl)-aminoalkanephosphonic acids have been prepared from α,ω-diaminoalkanes by reaction with chloromethanephosphonic acid (or an ester of a halogenoalkanephosphonic acid), followed by treatment with S-methylisothiouronium chloride.Ethylene diamine yielded 1-phosphonomethyl-2-iminoimidazolidine.A number of 1:1 salts of the α,ω-diamines and chloromethanephosphonic acid are also reported.Doubly charged zwitterionic structures are assigned to both ω-amino and ω-guanidino compounds on the basis of 31P and 13C nmr data.Thus the addition of an excess of acid (D2SO4) causes the 31P chemical shift to move to higher field, from ca. 8 to 14 ppm, whilst 1JPC increases from ca. 130 to 150 Hz.The 1H and 13C chemical shifts. of the terminal methylene groups in the polymethylene chain are unaffected by acidification.Fast atom bombardment mass spectrometry gives rise to characteristic + ions, frequently as the base peak, and to fragmentations involving the loss of phosphorous acid, or the formation of ions resulting from carbon-nitrogen or carbon-carbon cleavage.The compounds show activity against a number of fungal pathogens and other microbial organisms.Key words: Organophosphorus; fungicides; guanidinophosphonic acids; aminophosphonic acids; NMR spectroscopy; FAB mass spectrometry.
