ISSN 1214-0287 (on-line)
ISSN 1214-021X (printed)

Volume 1 (2003), No 3, p 169-173

Biological activity of binary mixtures of 2,4-D with some aminophosphonates

Janusz Sarapuk, Dorota Bonarska, Halina Kleszczynska

Address: Janusz Sarapuk, Department of Physics and Biophysics, Agricultural University, Norwida 25, 50-375 Wroclaw, Poland

Received 30th May 2003.
Published online 11th July 2003.

Full text article (pdf)

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).

aminophosphonates; biological activity; erythrocytes; binary mixtures

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.

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.