Ionic Liquids as Environmental Pollutants-Analysis of the Effect of Tetrabutylammonium Chloride on the Growth and Development of Wheat and Cucumber.

Ionic liquids are a huge group of chemical compounds that have found, or may, in the future, find, applications in various industries. These compounds are characterized by excellent physical, chemical, and biological properties, but a big problem is their environmental impact. One of the representatives of this group of compounds is tetrabutylammonium chloride ([TBA][Cl]). In this present study, the effects of [TBA][Cl] were evaluated on two popular plant species-a monocotyledonous plant-wheat (Triticum aestivum L.) and a dicotyledonous plant-cucumber (Cucumis sativus L.). The results showed that the compound caused a pronounced inhibition of plant growth and roots, as well as plant fresh weight yield. An increase in plant dry weight was observed at the same time. Despite the decrease in the content of photosynthetic pigments, no major changes were observed in chlorophyll fluorescence. All observed changes were strongly related to the applied concentration of the compound.

Ecotoxicity and bioremediation potential assessment of soil from oil refinery station area.

Purpose: The aim of the present study was to evaluate the toxicity and biodegradation potential of oil hydrocarbons contaminated soil samples obtained from different depths at an oil refinery station area. An approach involving chemical, microbiological, respirometry and ecotoxicity assessment of soil polluted by oil hydrocarbons was adopted, in order to determine the biodegradability of pollutants and ecotoxicological effects of natural attenuation strategy. Methods: The ecotoxicity of soil samples was evaluated using an ostracod test kit and a seed germination test. The results of the phytotoxicity assay were expressed as a percentage of seedling emergence and as the relative yield of fresh and dry biomass compared to control plants. The intrinsic biodegradation potential of the contaminated soil was examined using a Micro-Oxymax respirometer. Intrinsic biodegradation rates were estimated from the slopes of linear regressions curves plotted for cumulative O2 uptake. The obtained values were then entered in the mass balance equation for the stoichiometric reaction of hydrocarbon decomposition and converted per kg of soil per day. Results: Although the tested contaminants were biodegradable in the respirometric assay, they were slightly to moderately toxic to plants and extremely toxic to ostracods. The noxious effects raised with the increased concentration of contaminants. The monocotyledonous oat was more tolerant to higher concentrations of oil hydrocarbons than the other test plants, indicating its greater suitability for soil reclamation purposes. Conclusion: By assessing phytotoxicity and effect on ostracod mortality and progress of soil self-decontamination process, proper approach of reclamation of demoted area can be provided.

Reaction of spring barley seedlings and H. incongruens crustaceans to the presence of acetylsalicylic acid in soil.

Acetylsalicylic acid (ASA) is one of the more commonly used analgesic, antipyretic, and anti-inflammatory as well as anticoagulant drugs available in the OTC (over the counter) segment. Due to the considerable use of this drug, an attempt was made to determine the effect of ASA on the crustacean Heterocypris incongruens and the monocotyledonous plant spring barley. The tested compounds were introduced into soil in which these organisms "lived". The study showed that ASA had an adverse effect on seed germination potential as well as a negative effect on spring barley growth; however, and photosynthetic pigments content was observed only at the highest concentrations of the studied compounds. ASA did not cause oxidative stress in plants but did also cause disturbances in the growth of H. incongruens, without causing their mortality. As a result, ASA may have certain negative effects on both crustaceans and monocots.

Effect of diclofenac and naproxen and their mixture on spring barley seedlings and Heterocypris incongruens.

Nonsteroidal anti-inflammatory drugs (NSAIDs) are a popular group of drugs used worldwide. These drugs are also available over the counter, which implies that their consumption is not strictly regulated. They are released through wastewater and feces and can have adverse effects on the environment. The present study aimed to evaluate the effect of two NSAIDs, diclofenac (DCF) and naproxen (NAP), and their mixture (DCF + NAP) on spring barley seedlings and ostracods Heterocypris incongruens. The tested drugs had a negative impact on bivalve ostracods and the studied plants. DCF was the most toxic toward ostracods, while spring barley seedlings were affected the most by NAP. The application of the tested compounds and their mixture resulted in a decrease in fresh weight yield and the content of photosynthetic pigments. In addition, an increase in H2O2 and proline content and changes in the activity of antioxidant enzymes (POD, APX, CAT, and SOD) were observed.

Enzymatic Activity and Its Relationship with Organic Matter Characterization and Ecotoxicity to Aliivibrio fischeri of Soil Samples Exposed to Tetrabutylphosphonium Bromide.

This study aimed to determine the impact of tetrabutylphosphonium bromide [TBP][Br] on the soil environment through an experiment on loamy sand samples. The tested salt was added to soil samples at doses of 0 (control), 1, 10, 100, and 1000 mg kg-1 dry matter (DM). During the experiment, the activity of selected enzymes involved in carbon, phosphorus, and nitrogen cycles, characteristics of organic matter with Fourier-transform infrared (FT-IR) spectroscopy, and toxicity of soil samples in relation to Aliivibrio fischeri were determined at weekly intervals. The results showed that low doses of [TBP][Br] (1 and 10 mg kg-1 DM) did not have much influence on the analyzed parameters. However, the addition of higher doses of the salt into the soil samples (100 and 1000 mg kg-1 DM) resulted in a decrease in the activity of enzymes participating in the carbon and phosphorus cycle and affected the activation of those enzymes involved in the nitrogen cycle. This may be due to changes in aerobic conditions and in the qualitative and quantitative composition of soil microorganisms. It was also observed that the hydrophobicity of soil organic matter was increased. Moreover, the findings suggested that the soil samples containing the highest dose of [TBP][Br] (1000 mg kg-1 DM) can be characterized as acute environmental hazard based on their toxicity to Aliivibrio fischeri bacteria. The increased hydrophobicity and ecotoxicity of the soil samples exposed to the tested salt were also positively correlated with the activity of dehydrogenases, proteases, and nitrate reductase. Observed changes may indicate a disturbance of the soil ecochemical state caused by the presence of [TBP][Br].

The reaction of cucumber to the introduction of ionic liquids into the soil.

This paper presents the influence of two bromides, tetrabutylammonium and tetrabutylphosphonium, on the growth and development of cucumber seedlings. The tests were performed at two dates, i.e. 10 and 20 days, after the introduction of increasing amounts of ionic liquids (ILs) into the soil. The applied ILs showed phytotoxicity dependent mainly on the concentration of the substance, which is proved by the inhibition of the length of aboveground parts and their roots and the yield of cucumber fresh mass, from which EC50 values were calculated. The phytotoxicity symptoms were the result of oxidative stress, one of the manifestations of which was a decrease in assimilative pigments, linearly correlated with an increase in bromide concentration in the medium. The stress is also proven by the large increase in hydrogen peroxide, malondialdehyde and free proline in cucumber leaves. The reaction of this plant to oxidative stress was an increase in the activity of antioxidative enzymes such as catalase and peroxidase. As a result of statistical analysis, it was proved that all changes of biomarkers of phytotoxicity of examined ILs and oxidative stress indicators in cucumber seedlings depended more on the applied concentration of these salts than on the date of the study.

Ecotoxicity of ammonium chlorophenoxyacetate derivatives towards aquatic organisms: Unexpected enhanced toxicity upon oxygen by sulfur replacement.

Phenoxyacetate herbicides, such as 2,4-D and MCPA, having a high toxicity to non-target organisms are commonly used for controlling broadleaf weeds in agriculture. However, novel and environmentally friendly analogs are constantly sought after. For this purpose, various substituents at the phenyl group have been tested to find the optimal balance between the potent herbicidal activity and safety for non-target species. In this work, we investigated the influence of the oxygen by sulfur replacement in the phenoxy moiety of ammonium chlorophenoxyacetates on the toxicity towards aquatic organisms, such as bacteria (Vibrio fischeri), water flea (Daphnia magna) and freshwater fish (Pimephales promelas) by determining experimental (Microtox® test - V. fischeri) and predicted (ACD Lab Percepta software - D. magna, P. promelas) EC50/LC50 values. The achieved results showed that in contrary to the literature observations, where O-compounds were more toxic than their S-analogs (urea/thiourea), the O/S replacement in chlorophenoxyacetate significantly increased ecotoxicity of the S-analogs (up to 11 times). Moreover, one- and two-substituted phenoxyacetates in the form of ammonium salts were less toxic to V. fischeri than the commercially available phenoxy herbicides in the acid form. The logP/logD values were also calculated to understand hydro/lipophilic nature of the investigated compounds and differences in their toxicity.

Phytotoxicity of ionic liquids.

Ionic liquids (ILs) have been one of the most interesting chemical entities over the last two decades and have been investigated by numerous scientists all over the world. However, during IL research, it has been shown that these compounds present toxicity to both terrestrial and aquatic plants, among others. The phytotoxicity of ILs depends on the type of cation, the length of the alkyl chain in the substituent or enantioselectivity, on the concentration used, and, it appears that the type of anion may also have an impact on toxicity. The toxic effects of ILs on plants also depend on the conditions under which such tests are conducted. The results may help facilitate the development of protective environmental measures against IL-induced negative effects, but they may also be used in various landscape-related areas, such as herbology, to design new substances with weed killing properties.

Biochemical Responses of Wheat Seedlings on the Introduction of Selected Chiral Ionic Liquids to the Soils.

In this study, new chiral ionic liquids (CILs) were obtained from the natural-origin material (1 R,2 S,5 R)-(-)-menthol. The physicochemical characteristics of the studied imidazolium salts were investigated. The obtained 3-ethyl-1-[(1 R,2 S,5 R)-(-)-menthoxy-methyl]imidazolium salts are nonvolatile, nonflammable, and stable in air, in contact with water, and in commonly used organic solvents. The influences of the obtained chiral salts on physiological and biochemical parameters were determined for wheat ( Triticum aestivum L.) seedlings. Both salts led to changes in plant metabolism, which resulted in decreased assimilation pigments, decreased fresh weight, and increased dry weight and proline in wheat seedlings. Moreover, the growth of the above-ground parts and roots was inhibited. Additionally, there was a drop in the potential and germination capacity of wheat seeds after using the highest concentrations of the ionic liquids. The salts caused oxidative stress in wheat seedlings, which was demonstrated by increased malondialdehyde content. In response, the plants engaged their defensive system against free oxygen radicals, which resulted in increased catalase and peroxidase activity and decreased H2O2 levels in the plants. There were no changes in the activity of superoxide dismutase. All of the changes observed in the levels of determined biomarkers of oxidative stress in the plants were linearly correlated with the increase in the concentrations of the chiral ionic liquids in the soil. The salt with hexafluorphosphate anion exhibited slightly higher toxicity toward wheat seedlings than the other salt. The CILs led to premature aging of plants, which was demonstrated by the increase in peroxidase activity and a decrease of chlorophyll in the seedlings. The experiment also showed good correlation between the increase in peroxidase activity and the decrease in chlorophyll level, which proves that the decrease in chlorophyll content resulted from not only the increase in CILs concentration in the soil but also the increased POD activity, which leads to the damage of chlorophyll particles.

Ammonium haloacetates - An alternative to glyphosate?

This study shows the design, synthesis and evaluation of eco(phyto)toxic and herbicidal activities of quaternary ammonium salts (QASs), derived from haloacetic acids, in context of the search for safer alternatives to the commonly used herbicide, N-(phosphonomethyl)glycine (glyphosate). The structure of the investigated QASs refers to the heteroatom sequence in the anion of glyphosate in which the (P-C)-N nitrogen atom was replaced by one or more halogens (F, Cl). The ecotoxicity of the synthesized QASs was tested against luminescent marine bacteria Vibrio fischeri (Microtox® test) and the crustaceans Heterocypris incongruens (Ostracodtoxkit F™). The phytotoxic effect of QASs was also studied with respect to spring barley (Hordeum vulgare) and common radish (Raphanus sativus L. radicula Pers.), whereas herbicidal activity was investigated in relation to popular weeds species gallant soldier (Galinsoga parviflora Cav.) and common sorrel (Rumex acetosa L.). The results showed that toxicity of the synthesized QASs depends on a number of halo-substituents, especially for bioluminescent bacteria Vibrio fischeri for which EC50 values were those varying the most. Phytotoxicity tests proved that the investigated QASs had a similar high, toxic effect both on monocotyledonous and dicotyledonous plants with exception of DIPA - DCA. Moreover, their herbicidal activity against common sorrel was comparable to glyphosate.

Role of cation structure in the phytotoxicity of ionic liquids: growth inhibition and oxidative stress in spring barley and common radish.

The present study determines the influence of three ionic liquids (ILs) containing cations with diversified structure on the growth and development of spring barley seedlings and common radish leaves. Increasing amounts of 1-butyl-1-methylpyrrolidinium hexafluorophosphate [Pyrrol][PF6], 1-butyl-1-methylpiperidinium hexafluorophosphate [Piper][PF6], and 1-butyl-4-methylpyridinium hexafluorophosphate [Pyrid][PF6] were added to the soil on which both plants were cultivated. The results of this studies showed that the applied ILs were highly toxic for plants, demonstrated by the inhibition of length of plant shoots and roots, decrease of fresh mass, and increase of dry weight content. Common radish turned out to be the plant with higher resistance to the used ILs. The differences in the cation structure did not influence phytotoxity of ILs for spring barley. Furthermore, all ILs led to a decrease of photosynthetic pigments, which was directly followed by decreased primary production in plants. Oxidative stress in plants occurred due to the presence of ILs in the soil, which was demonstrated by the increase of malondialdehyde (MDA) content, changes in the H2O2 level, and antioxidant enzymes such as superoxide dismutase (SOD), catalase (CAT), and peroxidase (POD). The changes in the chlorophyll contents and the increase of POD activity turned out to be the most significant oxidative stress biomarkers in spring barley and common radish. Both spring barley and radish exposed to ILs accumulated a large amount of fluoride ion.

Changes in growth and physiological parameters of spring barley and common radish under the influence of 1-butyl-2,3-dimethylimidazolium tetrafluoroborate.

Ionic liquids (ILs) constitute a large group of chemical substances, which, thanks to their desirable properties, still attract attention of scientists and representatives of the industry. This may lead to a greater commercial use of these compounds, which will undoubtedly lead to the contamination of soils, constituting the basis of plant vegetation, with these substances. This paper presents effect of 1-butyl-2,3-dimethylimidazolium tetrafluoroborate [BMMIM][BF4] on the growth and development of spring barley and common radish and on the physiological and biochemical changes in these plants. The used IL was characterized by relatively high toxicity for the monocotyledonous plant, which was exhibited by shortening of the plant length and their root length, decreasing the fresh weight yield. Moreover, [BMMIM][BF4] led to the decrease in the content of all photosynthetic pigments in spring barley seedlings, reflecting the decrease in the fresh yield. Furthermore, the increase of malondialdehyde (MDA) level and changes in contents of hydrogen peroxide (H2O2) and the activity of antioxidant enzymes, that is, superoxide dismutase (SOD), catalase (CAT), and peroxidase (POD) may suggest the occurrence of oxidative stress in spring barley. The decrease in the content of photosynthetic pigment and the increase of POD activity constitute the most reliable markers of oxidative stress and, at the same time, the signs of early aging of spring barley plants. Common radish was the plant with a very high tolerance for the used IL, which can be indicated by, that is, EC50 values, determined based on inhibition of root length, plant length, and fresh weight yield.

Comparison of the effect of ionic liquids containing hexafluorophosphate and trifluoroacetate anions on the inhibition of growth and oxidative stress in spring barley and common radish.

Ionic liquids are a group of chemical compounds with chemical properties that are of great interest to various fields of science and industry. However, commercial use of these substances raises concern because they may threaten the natural ecosystems. The present study used 2 types of (-)-menthol-containing imidazolium chiral ionic liquids: 1-[(1R,2S,5R)-(-)-menthoxymethyl]-3-methylimidazolium hexafluorophosphate [Im-Men][PF6 ] and 1-[(1R,2S,5R)-(-)-menthoxymethyl]-3-methylimidazolium trifluoroacetate [Im-Men][CF3 CO2 ]. The effects of these compounds on growth and development of spring barley (Hordeum vulgare) and common radish (Raphanus sativus L. subvar. radicula Pers.) were investigated. The present study demonstrated that chiral ionic liquids produced a relatively high phytotoxicity, by shortening the plants' lengths and roots, thus causing a decline in the experimental plants' fresh weights. The investigated ionic liquids also led to a reduction in photosynthetic pigment levels, changes in hydrogen peroxide and malondialdehyde content, and changes in the activities of superoxide dismutase, catalase, and peroxidase in both plants. Changes in these enzymes were used to indicate oxidative stress levels in spring barley and common radish. It was demonstrated that imidazolium ionic liquid-induced phytotoxicity depended largely on the type of anion. The liquid [Im-Men][PF6 ] exhibited higher toxicity toward spring barley and common radish seedlings. Common radish was more resistant to chiral ionic liquids. Environ Toxicol Chem 2017;36:2167-2177. © 2017 SETAC.

Growth inhibition and efficiency of the antioxidant system in spring barley and common radish grown on soil polluted ionic liquids with iodide anions.

Ionic liquids (ILs) constitute a huge group of substances that are increasingly common in the commercial use. This situation may lead to the contamination of the soil environment which being the basic of plants vegetation. This paper presents the effect of four ILs with I- anion on the growth and development of spring barley (Hordeum vulgare) and common radish (Raphanus sativus L. subvar. radicula Pers) and changes in metabolism of the plants. Seedlings of spring barley and common radish cultivated on soil with increasing ILs concentration exhibited typical phytotoxicity symptoms. A considerable reduction of shoot and root lengths, decrease of fresh weight (FW) and increase of dry weight (DW) occurred in both test plants. Ionic liquids concentration increase in soil was correlated with the decrease of concentrations of all photosynthetic pigments in the plants. The observed increase of malondialdehyde (MDA) concentration and changes in the H2O2 level indicated presence of oxidative stress in spring barley and common radish, which usually led to the increase of superoxide dismutase (SOD), catalase (CAT) and peroxidase (POD) activity. The most reliable biomarker of oxidative stress was chlorophyll level and changes in POD activity.

Effect of Quaternary Ammonium Salts with Fluorine Atoms on Selected Weed Species.

This study investigated the effects of four structurally different quaternary ammonium salts (QASs), i.e., tetrabutylammonium tetrafluoroborate [TBA][BF4], tetrahexylammonium tetrafluoroborate [THA][BF4], tetrabutylammonium hexafluorophosphate [TBA][PF6], and tetrahexylammonium hexafluorophosphate [THA][PF6], on the growth and development of three weed species: gallant soldier (Galinsoga parviflora Cav.), white goosefoot (Chenopodium album L.) and common sorrel (Rumex acetosa L.). The examined compounds were applied in the form of foliar spraying and soil application. Strong herbicidal properties of the examined compounds were demonstrated in case of their soil application. Growth inhibition of plant shoots and roots was greater with soil application than with foliar treatment. The strongest herbicidal activity of compounds was demonstrated with [TBA][BF4] have demonstrated [TBA][BF4] and [TBA][PF6] applied to the soil, while [THA][BF4] demonstrated the weakest herbicidal action. The increased concentration of applied QASs caused a decrease in the assimilation pigments, change in dry weight content and inhibition of length of shoots and roots.

The effect of the number of alkyl substituents on imidazolium ionic liquids phytotoxicity and oxidative stress in spring barley and common radish seedlings.

Increasing amounts of two ILs: 1-butyl-3-methylimidazolium hexafluorophosphate [BMIM][PF6] and 1-butyl-2,3-dimethylimidazolium hexafluorophosphate [BMMIM][PF6], were introduced to soil in which spring barley (Hordeum vulgare) and common radish (Raphanus sativus L. subvar. radicula Pers.) seedlings were cultivated, in order to evaluate the phytotoxicity of ionic liquids with imidazolium cation with two or three alkyl substituents attached. The results of the study i.e. the inhibition of the length of plants and their roots, as well as the yield of fresh weight of plants, clearly showed that differences in the number of substituents did not affect the toxicity of these ILs. Although, radish was more resistant to the applied ionic liquids than barley. Ionic liquids led to a decrease in the content of all assimilation pigments and induced oxidative stress in the plants, as showed by an increase in malondialdehyde (MDA) content, and changes in the level of H2O2 and antioxidant enzymes: superoxide dismutase (SOD), catalase (CAT) and peroxidase (POD). The best biomarkers of oxidative stress in both plants were the changes in chlorophyll content and the increase in POD activity. Both spring barley and radish exposed to [BMIM][PF6] and [BMMIM][PF6] accumulated a large amount of fluoride ions, which further increased the toxicity of these compounds for both plants.

Oxidative stress in spring barley and common radish exposed to quaternary ammonium salts with hexafluorophosphate anion.

Quaternary ammonium salts (QAS), including ionic liquids (ILs), constitute a huge group of substances, which due to their desirable physical and chemical properties still attracts great interest in many industrial sectors. An increased concentration of this compound in the environment may lead to the contamination of the natural environment and may pose a potential threat to all organisms, including terrestrial higher plants. The present study demonstrates the interaction of three QAS with PF6(-) anions - tetramethylammonium [TMA][PF6], tetrabutylammonium [TBA][PF6], and tetrahexylammonium [THA][PF6] hexafluorophosphates - and its impact on the physiological and biochemical changes in spring barley seedlings and common radish plants. A similar study was also carried out by introducing the inorganic salt - ammonium hexafluorophosphate [A][PF6] to the soil; the results showed the soil became highly toxic to both plants. All the salts used led to significant changes in the metabolism of both spring barley and common radish which can be evidenced, for example, by a decrease in the content of chlorophyll a (Chla), chlorophyll b (Chlb), and total chlorophyll (Chla + b), as well as carotenoids (Car). The decrease in assimilation pigments was linearly correlated with an increasing concentration of QAS in the soil. QAS and [A][PF6] led to the formation of oxidative stress in both experimental plants, as evidenced by an increase in malondialdehyde (MDA) content in their cells and the changes in H2O2 level. In response to stress, the plants synthesized enzymatic free radicals (ROS) scavengers that lead to changes in the activity of superoxide dismutase (SOD) and catalase (CAT), as well as significantly increased peroxidase (POD) activity. A decrease in the content of assimilation pigments and an increased POD activity are the most reliable indices of oxidative stress, and concurrently the signs of premature plants aging. Common radish proved to be more resistant to the presence of QAS in the soil compared to spring barley.

Evaluation of the effect of tetraethylammonium bromide and chloride on the growth and development of terrestrial plants.

Quaternary ammonium salts (QAS), which also include ionic liquids, constitute a vast group of chemical compounds that are increasingly common in the commercial use. This situation may lead to the contamination of the natural environment and may constitute a potential threat to all its elements, including terrestrial higher plants. This paper presents the effect of tetraethylammonium chloride [TEA][Cl] and tetraethylammonium bromide [TEA][Br] on the growth and development of spring barley and common radish. The applied QAS were characterized with phytotoxicity dependent on the concentration of compound and characteristics of the study plants. Spring barley turned out to be highly susceptible plant to the analyzed compounds, which was confirmed by % inhibition of length of plants, root length and fresh weight of plants and by calculated values for EC50, NOEC as well as LOEC. On the contrary, a common radish revealed the resistance to QAS used in the study; although, phytotoxic symptoms were still observed when high concentrations of dry weight of soil were applied (1000, 3000 and 5000 mg/kg). The applied QAS caused oxidative stress symptoms, mainly in spring barley seedlings, which were manifested by decreased assimilation of pigments content, increased hydrogen peroxide (H2O2) and malondialdehyde (MDA) content in plant cells and with a changed activity of superoxide dismutase (SOD), catalase (CAT) and peroxidase (POD).

Quaternary ammonium salts with tetrafluoroborate anion: Phytotoxicity and oxidative stress in terrestrial plants.

This paper discusses the impact of four quaternary ammonium salts (QAS) such as tetraethylammonium tetrafluoroborate [TEA][BF4], tetrabutylammonium tetrafluoroborate [TBA][BF4], tetrahexylammonium tetrafluoroborate [THA][BF4], and tetraoctylammonium tetrafluoroborate [TOA][BF4] on the growth and development of spring barley and common radish. Analogous tests were performed with the inorganic salt ammonium tetrafluoroborate [A][BF4] for comparison purposes. Results indicated that the phytotoxicity of the QAS applied is dependent on the concentration of the substance and their number of carbon atoms. The most toxic compound was [TBA][BF4], causing the greatest drop in fresh weight of both study plants, similar to the phytotoxic effects of [A][BF4]. All the tested compounds caused oxidative stress in spring barley and common radish seedlings due to a drop in the chlorophyll content. Stress was also observed in plants, which was indicated by the increased level of ROS (reactive oxygen species) such as H2O2 and lipid peroxidation of MDA (malondialdehyde). Due to the stress, both plants displayed changes in the activity of antioxidative enzymes such as superoxide dismutase (SOD), catalase (CAT) and peroxidase (POD). Based on the results of the study, it was concluded that changes in chlorophyll levels and peroxidase activity are the best biomarkers to determine oxidative stress in plants.

The phytotoxicity of ionic liquids from natural pool of (-)-menthol with tetrafluoroborate anion.

Over the last several decades, ionic liquids have become a promising alternative to conventional organic solvents. Initially, ionic liquids were described as "environmentally friendly" substances. However, the results of numerous studies proved that the effects of these compounds on individual ecosystems might be adverse. The presented paper discusses the effect of ionic salts containing natural chiral substituent: (1R,2S,5R)-(-)-menthol in cation and a tetrafluoroborate anion of a general formula of [Cn-Im-Men][BF4] of implementation into the soil on the growth of spring barley and common radish in their early development stages. The obtained results showed that the greatest phytotoxicity was exhibited by ionic liquids containing substituents with the smallest possible number of carbon atoms. The further increase in the length of the chain did not increase the toxicity of these salts for terrestrial plants. Moreover, a compound with a substituent having a chain length of 11 carbon atoms was found to be non-toxic to common radish. The experiment under discussion showed also the effect of these tetrafluoroborates, used in the form of spray, on the development of common sorrel, gallant soldier and white goosefoot. The tests carried out also showed that the most toxic were the compounds with 1 and 3 carbon atoms. The phytotoxicity of tetrafluoroborates was positively correlated with the concentration of these compounds in the soil and was dependent on the genetic features of the genres and varieties of plants used in the experiment.