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Molecules 2017, 22(7), 1132; doi:10.3390/molecules22071132

Novel N-Arylaminophosphonates Bearing a Pyrrole Moiety and Their Ecotoxicological Properties

1
Department of Organic Chemistry, Faculty of Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland
2
Faculty of Mathematics and Natural Science, Jan Długosz University in Częstochowa, 13/15 Armii Krajowej Av., 42-200 Częstochowa, Poland
3
M.Sc. Student at the Faculty of Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland
*
Authors to whom correspondence should be addressed.
Received: 9 June 2017 / Revised: 4 July 2017 / Accepted: 5 July 2017 / Published: 7 July 2017
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Abstract

A wide range of biological activities of aminophosphonates predisposes them to find applications as anticancer, antiviral, antimicrobial, antifungal, or herbicidal agents. Despite a number of positive aspects of the use of aminophosphonates, their applications may cause a risk to the environment, which is well exemplified by the case of glyphosate. Therefore, scientists see a pressing need to rate ecotoxicity of aminophosphonates. Nowadays, it is recommended to use comprehensive tools to carry out appropriate and effective risk assessments of toxic substances. For these purposes, tests based on the acute toxicity of the luminescent bacteria Aliivibrio fischeri, as well as the measurement of sub-chronic toxicity of the crustacean Heterocypris incongruens seem to be the most convenient. A series of five diphenyl N-arylamino(pyrrole-2-yl)methylphosphonates was synthesized and preliminary evaluation of their ecotoxicological properties was performed. In order to carry out such investigations, we applied the two biotests mentioned above. Results showed that the N-(4-nitrophenyl) derivative was the most toxic for bacteria in comparison to other tested compounds. As for crustaceans, N-phenyl and N-naphthyl derivatives were found to be the most harmful, simultaneously being relatively harmless for bacteria. Such a phenomenon are discussed in correlation with the literature, while its reason is discussed with respect to the aspect of structure of the tested compounds. View Full-Text
Keywords: aminophosphonates; pyrrole derivatives; aza-Pudovik reaction; ecotoxicology; A. fischeri test; H. incongruens test aminophosphonates; pyrrole derivatives; aza-Pudovik reaction; ecotoxicology; A. fischeri test; H. incongruens test
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Lewkowski, J.; Morawska, M.; Kaczmarek, A.; Rogacz, D.; Rychter, P. Novel N-Arylaminophosphonates Bearing a Pyrrole Moiety and Their Ecotoxicological Properties. Molecules 2017, 22, 1132.

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