Dg. Cameron et al., ORGANOPHOSPHORUS COMPOUNDS AS POTENTIAL FUNGICIDES .2. AMINOALKANE-, GUANIDINOALKANE-, AND THIOUREIDOALKANE-PHOSPHONIC ACIDS - PREPARATION,SPECTROSCOPY, AND FUNGICIDAL ACTIVITY, Phosphorus, sulfur and silicon and the related elements, 83(1-4), 1993, pp. 21-37
A range of alpha-amino-, omega-amino-, alpha-guanidino-, and omega-gua
nidinoalkanephosphonic acids has been prepared for the purpose of stud
ying their spectroscopic features and fungicidal activity. In addition
, alpha-thioureido-octanephosphonic acid and thioureylene-1,1-bis(1-oc
tanephosphonic acid) were isolated during the preparation of alpha-gua
nidino-octanephosphonic acid. P-31, H-1, and C-13 nmr spectral data wh
ich were obtained for solutions of the amino- and guanidino-compounds
in D2O or D2O/D2SO4, and for the thioureido compounds in DMSO-d(6), ar
e discussed together with previously reported data for the aminophosph
onic types. FAB mass spectrometry generally gives strong pseudomolecul
ar ions [MH](+) for the zwitterionic amino- and guanidino-compounds wi
th relatively simple fragmentations. Fungicidal activity of the alpha-
aminophosphonic acids was found to be greater than for the omega-amino
compounds, with maximum activity at a chain length of three carbon at
oms when used as a seed dressing for the control of Drechslera spp. Mo
derately good activity was shown by the thioureido compounds against a
number of fungal organisms in vitro but the guanidino-compounds exhib
ited low activity.