Faculty of Science and Technology, Jan Długosz University in Częstochowa, 42-200, Częstochowa, Armii Krajowej 13/15, Poland.
Department of Organic Chemistry, Faculty of Chemistry, University of Łódź, Tamka 12, 91-403, Łódź, Poland.
Ecotoxicol Environ Saf. 2020 May;194:110331. doi: 10.1016/j.ecoenv.2020.110331. Epub 2020 Mar 5.
In this paper, comparison of ecotoxicological and herbicidal effect of newly synthesized N‑[(phosphono)(aryl)methyl]glycines 1a-g (C-substituted glyphosate derivatives) with pure glyphosate (N-phosphonomethylglycine) (2) was demonstrated. All of tested glyphosate derivatives (1a-g) in contrast to glyphosate, were found to be completely safe for oat (Avena sativa) and classified as not harmful for marine bacteria Aliivibrio fischeri. Compounds 1a-g were also found rather harmless to radish (Raphanus sativus) as compared to N-phosphonomethylglycine, but they were moderately toxic against freshwater crustaceans Heterocypris incongruens. One of synthesized compounds, namely N-[(phosphono)(4-hydroxyphenyl)methyl]glycine (1f) was found to possess stronger herbicidal properties against gallant soldier (Galinsoga parviflora) and common sorrel (Rumex acetosa) when compared to pure glyphosate and demonstrated total death of these weeds being ranked 1 in the European Weed Research Council (EWRC) scale. Considering lower phytotoxicity of compound 1f against cultivated plants and tested microorganisms when compared to pure glyphosate, this aminophosphonate may be good candidate for further, more comprehensive study toward its agrochemical application, especially that this active agent demonstrated much stronger herbicidal properties than N-phosphonomethylglycine.
本文比较了新合成的 N-[(膦酸基)(芳基)甲基]甘氨酸 1a-g（C-取代草甘膦衍生物）与纯草甘膦（N-膦酸甲基甘氨酸）（2）的生态毒理学和除草效果。与草甘膦相比，所有测试的草甘膦衍生物（1a-g）被发现对燕麦（Avena sativa）完全安全，并被归类为对海洋细菌 Aliivibrio fischeri 无害。与 N-膦酸甲基甘氨酸相比，化合物 1a-g 对萝卜（Raphanus sativus）的危害也较小，但对淡水甲壳类动物异盘藻（Heterocypris incongruens）具有中度毒性。合成的一种化合物，即 N-[(膦酸基)(4-羟基苯基)甲基]甘氨酸（1f）被发现对美丽马缨丹（Galinsoga parviflora）和酸模（Rumex acetosa）具有比纯草甘膦更强的除草特性，并且这些杂草的全部死亡被欧洲杂草研究理事会（EWRC）评为 1 级。考虑到与纯草甘膦相比，化合物 1f 对栽培植物和测试微生物的植物毒性较低，这种氨基膦酸酯可能是进一步更全面研究其农用化学品应用的良好候选物，特别是该活性物质表现出比 N-膦酸甲基甘氨酸更强的除草特性。
