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1

Fluorowane aminofosfoniany

Cytlak Tomasz, Kaźmierczak Marcin

Wiadomości Chemiczne

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2020

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[Z] 74, 3-4

203--230

EN

Aminophosphonates and aminophosphonic acids are important substrates in the study of biochemical processes. They have found a wide range of applications as enzyme inhibitors, agrochemicals and pharmaceuticals in the areas of biological and medicinal chemistry. Due to the unique properties of fluorine atom, such as high electronegativity and electron density, its presence in aminophosphonates’ moiety can influence chemical reactivity, biological activity, metabolic stability, chemical bonding ability and solubility. Recently, special interest has been focused on synthesis of fluorinated aminophosphonates due to their promising applications in the fields of bioorganic chemistry. Many of these compounds exhibit antitumor, antibacterial and antifungal activities [1-3].

2

Biodegradacja związków fosfonowych przez grzyby

Wieczorek Dorota, Lipok Jacek

Wiadomości Chemiczne

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2020

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[Z] 74, 1-2

33--55

EN

Phosphonates are the group of organophosphorus compounds, which are characterized by the presence of covalent bond(s) between carbon and phosphorus atom in their structure. Both; the natural and synthetic phosphonic compounds, are encountered in various ecosystems, however because of their wide range of applications, the latter ones are considerably more frequently discussed. Regarding the broad spectrum of biological activity, capability to chelate metal cations and environmental stability of direct carbon to phosphorus bond under physiological conditions, phosphonic compounds found a variety of applications e.g. as pesticides, drugs, anticorrosive agents, additives to surfactants and flame resistant (partially)polymers. Such massive use of phosphonates, together with mentioned environmental stability of those compounds, results in their common presence as xenobiotic environmental pollutants. Scientific efforts dedicated to recognising the fate and biodegradation of phosphonic compounds in the environment had begun in 80’s last century. Currently it is known that many microorganisms, mainly bacteria, but also fungi, are able to decompose the C-P bond. Interestingly however, the number of known species of fungi that are able to biodegrade and/or to bio-transform the phosphonates, is relatively low. It seems to be surprising, because especially the fungi are known from their impressive skills to adaptation to various nutritional conditions. Such a thesis may be supported by the fact that the process of biodegradation of phosphonates may occur via several pathways. Enzymes which are known to catalyse this process are phosphonoacetaldehyde hydrolase, phosphonoacetate hydrolase, phosphonopyruvate hydrolase and C-P lyase complex. This article briefly presents the issue of degradation pathways of phosphonates, and the role of phosphonate- degrading fungi.

3

Analiza zawartości fosfonianów w materiale roślinnym

Kłosińska T., Archanowicz E., Antczak A., Radomski A., Zielenkiewicz T., Oszako T., Nowakowska J. A., Kubiak K. A., Tkaczyk M.

Przemysł Chemiczny

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2015

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T. 94, nr 6

894-899

PL

Opracowano metodę ilościowego oznaczania fosfonianów w tkankach roślinnych. Zaproponowana procedura oparta jest na reakcji tych jonów z jonami srebra w środowisku kwaśnym, w wyniku której strąca się osad metalicznego srebra. Ilość wolnego srebra, powstałego w wyniku działania fosfonianów, została oznaczona metodami spektrometrii fluorescencji rentgenowskiej XRF i spektrofotometrii UV-VIS. Metoda XRF jest mniej pracochłonna, lecz jej czułość to ok. 0,1 mg srebra, co nie stanowi wyniku zadowalającego w przypadku śladowych ilości fosfonianów w tkankach roślinnych. W przypadku spektrofotometrii UV-VIS, po roztworzeniu srebra w stężonym HNO₃, skompleksowaniu jonów Ag⁺ ditizonem, ekstrakcji chloroformem i bezpośrednim oznaczeniu spektrofotometrycznym bez usuwania wolnego ditizonu, uzyskano znacznie większą czułość, wynoszącą 0,03 μM srebra. Na podstawie ilościowej reakcji fosfonianów, srebra i ditizonu można oszacować zawartość fosfonianów w tkankach roślinnych.

EN

Concn. of PHO₃²⁻ ions in plant tissues was detd. by using reaction with Ag⁺ in acidic soln. to metallic Ag ppt. The amt. of Ag was detd. by X-ray fluorescence spectrometry (XRF) and UV-VIS spectrophotometry. The XRF method was less laborious, but its accuracy was lower. Its sensitivity was insufficient to det. very low concns. of phosphonates. The UV-VIS spectrophotometry, after Ag dissoln. in concd. HNO₃, complexation of Ag⁺ with dithizone, extn. with CHCl₃ and detn. without removal of free dithizone, showed a significantly higher sensitivity.

4

Wytwarzanie penicyliny G przez Penicillium chrysogenum jako marker biodegradacji związków fosfonoorganicznych

Wieczorek D., Gołaszewska L., Lipok J.

Przemysł Chemiczny

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2011

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T. 90, nr 5

1061-1065

5

Związki metaloorganiczne w syntezie fosfonianów

Prokopowicz M., Młynarz P., Kafarski P.

Wiadomości Chemiczne

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2010

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[Z] 64, 1-2

1-22

EN

Phosphonates constitute a class of compounds with variety of applications in organic synthesis (as reagents in the orner-Wadsworth-Emmons reaction), medicine (biologically active compounds) or industry (as e.g. water softeners) [1, 2]. Therefore, the original synthetic methods were developed in order to obtain phosphonates possessing vast and desired properties [3]. This work focuses on the methods employing metalloorganic compounds to a new C-P bond formation. This approach is achieved in most cases by substitution at a trigonal phosphorus atom. The reactions are characterized by high yields and lack of side-products what facilitates the isolation and purification of the target compounds. These benefits are provided mainly by application of lithium and magnesium derivatives. The other method involves modification of a ready molecule skeleton. The procedures utilizing a new C-C or C-halide bond formation are commonly used. Suitable for these synthetic routes are such soft nucleophiles as copper- zinc- and cadmium-organic compounds. Additionally, examples of an application of mercury-, lead- and aluminiumorganic reagents to the synthesis of other organic phosphorus compounds are discussed. Although their use is rather marginal, they appeared to be crucial for specific and original syntheses.

6

Związki fosfonowe w technologii płuczek wiertniczych w świetle badań laboratoryjnych

Zima G., Błaż S.

Nafta-Gaz

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2006

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R. 62, nr 10

510-514

PL

W artykule opisano wyniki badań laboratoryjnych nad zastosowaniem związków fosfonowych, jako środków regulujących parametry reologiczne i filtrację płuczek wiertniczych o różnej zawartości fazy stałej i zasoleniu. Przedstawione badania przeprowadzono z użyciem związków fosfonowych zdolnych do tworzenia związków kompleksowych z jonami metali i wykazujących wysoką aktywność chemisorpcyjną w stosunku do powierzchni minerałów ilastych. Na podstawie uzyskanych wyników zaproponowano nowe efektywne środki upłynniające do płuczek wiertniczych, szczególnie o dużej zawartości fazy stałej.

EN

Article presents investigations on phosphones effects on drilling mud parameters. Laboratory study gave new type of thinners for drilling muds with high concentrations of solids.