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Molecules 2018, 23(12), 3173; https://doi.org/10.3390/molecules23123173

Effect of New Thiophene-Derived Aminophosphonic Derivatives on Growth of Terrestrial Plants. Part 2. Their Ecotoxicological Impact and Phytotoxicity Test Toward Herbicidal Application in Agriculture

1
Faculty of Mathematics and Natural Science, Jan Długosz University in Częstochowa, 42-200 Częstochowa, 13/15 Armii Krajowej Av., Poland
2
Department of Organic Chemistry, Faculty of Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland
*
Authors to whom correspondence should be addressed.
Received: 15 November 2018 / Revised: 25 November 2018 / Accepted: 29 November 2018 / Published: 1 December 2018
(This article belongs to the Section Bioorganic Chemistry)
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Abstract

Background: The aim of this work was to evaluate phytotoxicity of the thiophene derivatives against three persistent weeds of a high degree of resistance (Galinsoga parviflora Cav., Rumex acetosa L., and Chenopodium album) as well as their ecotoxicological impact on Heterocypris incongruens. In addition, Aliivibrio fischeri was measured. Two of eight described aminophosphonates, namely dimethyl N-(2-methoxyphenyl)amino(2-thienyl)methylphosphonate (2d) and dimethyl N-(tert-butyl)- (2-thienyl)methylphosphonate (2h), have never been reported before. Methods: The phytotoxicity of tested aminophosphonates toward their potential application as soil-applied herbicides was evaluated according to the OECD 208 Guideline. Ecotoxicological properties of investigated compounds were made using the OSTRACODTOXKITTM and Microtox® tests. Results: Obtained results showed that four aminophosphonates have interesting herbicidal properties and N-(2-methylphenyl)amino- (2-thienyl)methylphosphonate (2a) was found to kill efficiently the most resistant plant Chenopodium album. None of the tested compounds showed important toxicity against Aliivibrio fischeri. However, their toxic impact on Heterocypris incongruens was significantly elevated. Conclusions: The aminophosphonate 2a showed herbicidal potential and it is not toxic against tested bacteria (EC50 over 1000 mg/L). It was found to be moderately toxic against ostracods [mortality 48% at 10 mg/kg of soil dry weight (s.d.w.)] and this problem should be solved by the use of the controlled release from a polymeric carrier. View Full-Text
Keywords: herbicidal activity; persistent weeds; Aliivibrio fischeri test; Heterocypris incongruens test; ecotoxicology; OECD standard herbicidal activity; persistent weeds; Aliivibrio fischeri test; Heterocypris incongruens test; ecotoxicology; OECD standard
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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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Rogacz, D.; Lewkowski, J.; Malinowski, Z.; Matusiak, A.; Morawska, M.; Rychter, P. Effect of New Thiophene-Derived Aminophosphonic Derivatives on Growth of Terrestrial Plants. Part 2. Their Ecotoxicological Impact and Phytotoxicity Test Toward Herbicidal Application in Agriculture. Molecules 2018, 23, 3173.

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