SUMMARY
A series of cyclic and acyclic aminophosphonates was synthesized for agrochemical application. The
compounds differed in the substituents at the carbon, nitrogen and phosphorus atoms. Their potential
biological activity was checked by studying their hemolytic potency, since hemolysis of erythrocytes
by various compounds was found earlier to be a good indicator of their pesticidal efficiency. A
series of hemolytic experiments permitted us to check the pesticidal efficiency of
aminophosphonates and to determine what structural features of aminophosphonates are responsible
for it.
Parallelly, we studied the hemolytic efficiency of binary mixtures of the aminophosphonates with
the well-known herbicide 2,4-dichlorophenoxyacetic acid (2,4-D...) The aim was to check if potential
biological efficiencies could be enhanced in comparison with those found for individual components
due to interactions between aminophosphonates and 2,4-D. An analysis of the effects binary
mixtures was carried out by constructing graphs for both components of binary mixtures that give
the same hemolysis (the isobole method).
KEY WORDS
aminophosphonates; biological activity; erythrocytes; binary mixtures
REFERENCES
Agrawal D, Subramoniam A, Afaq F: Influence
of hexachlorocyclohexane on phosphoinositides
in rat erythrocyte membranes and brain. Toxicol
95:135-140, 1995.
Duchnowicz P, Koter M: Damage to the
erythrocyte membrane caused by
chlorophenoxyacetic herbicides. Cell Mol Biol
Lett 8:25-30, 2003.
Duchnowicz P, Koter M, Duda W: Damage of
erythrocyte by phenoxyacetic herbicides and
their metabolites. Pest Biochem Physiol 74:1-7, 2002.
Forlani G, Lejczak B, Kafarski P, Wieczorek P:
Mode of action of herbicidal derivatives of
aminomethylenebiophosphonic acid. Part II.
Reversal of herbicidal action by aromtic amino
acids. J Plant Growth Regul 16:147-152, 1997.
Gisi U: Synergistic action of fungicides in mixtures.
Phytopathol 86:1273-1279, 1996.
Grzys E, Bielecki K, Sarapuk J:
Aminophosphonate-induced changes of
betacyanine and ionic efflux. Z Naturforsch
56c:349-352, 2001.
Kleszczynska H, Sarapuk J, Bonarska D: The
hemolytic toxicity of some new
aminophosphonates. Cell Mol Biol Lett 6:271-275, 2001.
Kleszczynska H, Bonarska D, Bielecki K, Sarapuk J: The hemolytic and physiological
activities of mixtures of some phenoxy and
organophosphorous herbicides. Cell Mol Biol
Lett 8:55-61, 2003.
Kortenkamp A, Altenburger R: Synergisms
with mixtures of xenoestrogens: A reevaluation
using the method of isoboles. Sci Total Environ
221:59-73, 1998.
Mora A, Earle ED: Combination of
Trichoderma harzianum endochitinase and
membrane-affecting fungicide on control of
Alternaria leaf spot in transgenic brocolli plants.
Appl Microbiol Biotechnol 55:306-310, 2001.
Oruc EO, Uner N: Effects of 2,4-Diamin on
some parameters of protein and carbohydrate
metabolisms in the serum, muscle and liver of
Cyprinus carpio. Environ Pollution, Part C:267-272, 1999.
Oruc EO, Uner N: Combined effects of 2,4-D
and azinphosphometyl on antioxidant enzymes
and lipid peroxidation in liver of Oreochromis
niloticus. Comp Biochem Physiol Part C, 127:291-296, 2000.
Pape-Lindstrom PA, Lydy MJ: Synergistic
toxicity of atrazine and organophosphate
insecticides contravenes the response addition
mixture model. Environ Toxicol Chem 16:2415-2420, 1997.
Ponder E: Hemolysis and related phenomena. J A
Churchill Ltd, London, 1948.
Suwalsky M, Benites M, Norris B, Sotomayor P:
Toxic effects of the fungicide benomyl on cell
membranes. Comp Biochem Physiol Part C,
125:111-119, 2000.
Suwalsky M, Benites M, Villena F, Aguilar F, Sotomayor P: Interaction of 2,4-dichlorophenoxyacetic acid (2,4-D) with cell and
model membranes. Biochim Biophys Acta 125:111-119, 1996.
Suwalsky M, Quevedo L, Norris B, Benites M:
Toxic action of the herbicide 2,4-D on the
neuroepithelial synapse and on the nonstimulated
skin of the frog Caudiverbera caudiverbera.
Bull Environ Contam Toxicol 62:570-577, 1999.
Trela Z, Kleszczynska H, Sarapuk J: Physiological
and hemolytic toxicity of some
aminophosphonates. Z Naturforsch 56c:838-842, 2001.
Tripathi AM, Agarwal RA: Synergism in
tertiary mixture of pesticides. Chemosphere 35:2365-2374, 1997.
|
CITED
Bogomilova A, Hagele G, Troev K, Wagner E, Gunther M. Hydrogen bonding in alpha-aminophosphonic acids. Phosphorus Sulfur Silicon Relat Elem. 187: 165-180, 2012.
Wafa T, Amel N, Issam C, Imed C, Abdelhedi M, Mohamed H. Subacute effects of 2,4-dichlorophenoxyacetic herbicide on antioxidant defense system and lipid peroxidation in rat erythrocytes. Pestic Biochem Physiol. 99: 256-264, 2011.
Onita N, Sisu I, Penescu M, Purcarea VL, Kurunczi L. Synthesis, characterization and biological activity of some alpha-aminophosphonates. Farmacia. 58: 531-545, 2010.
Onita N, Sisu E, Lupea AX, Szabo R. Aminophosphonoic acids and derivatives - Antioxidant activity ranking. Rev Chim. 57: 1022-1024, 2006.
Onita N, Lupea AX, Sisu I, Lungu ME, Ivan E. Aminophosphoric acids and their derivatives. VIII. Classic and modem syntheses of new alpha-aminophosphates. Rev Chim. 56: 1261-1263, 2005.
|