Abstract
The aim of this work was to evaluate the impact of the thiophene-derived aminophosphonates 1–6 on seedling emergence and growth of monocotyledonous oat (Avena sativa) and dicotyledonous radish (Raphanus sativus L.), and phytotoxicity against three persistent and resistant weeds (Galinsoga parviflora Cav., Rumex acetosa L., and Chenopodium album). Aminophosphonates 1–6 have never been described in the literature. The phytotoxicity of tested aminophosphonates toward their potential application as soil-applied herbicides was evaluated according to the OECD (Organization for Economic and Cooperation Development Publishing) 208 Guideline. In addition, their ecotoxicological impact on crustaceans Heterocypris incongruens and bacteria Aliivibrio fischeri was measured using the OSTRACODTOXKITTM and Microtox® tests. Obtained results showed that none of the tested compounds were found sufficiently phytotoxic and none of them have any herbicidal potential. None of the tested compounds showed important toxicity against Aliivibrio fischeri but they should be considered as slightly harmful. Harmful impacts of compounds 1–6 on Heterocypris incongruens were found to be significant.
Highlights
Compounds bearing thiophene moiety are of increasing importance in various fields of science and technology [1]
The thiophene-based materials have found their application in organic electronics, where their semiconducting properties are exploited in thin film field-effect transistors and solar cells and in bioimaging, where their optical properties are utilized to monitor biological processes involving proteins and DNA
In search of better properties, we extended our studies to other thiophene-derived aminophosphonic esters, and we describe the synthesis of novel diphenyl amino(2-thienyl)methylphosphonates1–6 and investigations on their phyto- and ecotoxicological properties
Summary
Compounds bearing thiophene moiety are of increasing importance in various fields of science and technology [1]. Due to their multiple functional properties and chemical versatility, they are investigated in many aspects of material chemistry and engineering. Apart from above, thiophene oligomers are characterized by fluorescence frequency, being tunable from blue to near infrared depending on molecular structure [7].
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