Juliusz Pernak

Poznan University of Technology, Posen, Greater Poland Voivodeship, Poland

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Publications (156)342.47 Total impact

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    ABSTRACT: Novel herbicidal ionic liquids (HILs) containing different anions and cations derived from ammonium esterquats are prepared by employing a simple, inexpensive pathway.
    ChemInform 09/2015; 46(36). DOI:10.1002/chin.201536250
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    ABSTRACT: This study was focused on presenting a new class of ionic liquids (ILs) with anions of natural origin. The salts were obtained by hydrolysis of defined triglycerides or edible vegetable oils (coconut oil and canola oil) by quaternary ammonium hydroxides. The basic physicochemical properties of the obtained products were studied and their microbial and deterrent activity was determined. Additionally, their susceptibility to biodegradation was evaluated. The described synthesis pathway utilizes vegetable oils and quaternary ammonium hydroxides as reactants in order to obtain ILs with anions of natural origin, which are characterized by specific biological activity. The majority of the prepared ILs exhibited excellent feeding deterrent properties and could be classified as readily biodegradable compounds. The employed method is characterized by low cost of substrates, high yields and high purity of the obtained products. It might potentially find application as a tool to synthesize environmentally-friendly ILs with attractive properties for a wide range of applications.
    RSC Advances 07/2015; DOI:10.1039/C5RA11710K · 3.84 Impact Factor
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    ABSTRACT: Novel herbicidal ionic liquids (HILs) containing different anions and cations derived from ammonium esterquats were prepared by employing a simple, inexpensive pathway. The basic physicochemical properties of the synthesized salts (such as density, viscosity, refractive index, solubility and thermal stability) were determined. Additionally, their herbicidal efficacy was evaluated under greenhouse and field conditions with subsequent assessment of biodegradability and toxicity (acute oral toxicity towards rats and rainbow trout, growth inhibition test of green algae and acute immobilization test using water flea). The results of greenhouse and field experiments revealed that the herbicidal activity of HILs comprising long alkyl chains has exceeded that of commercial plant protection products. The HIL containing the di(tallowoyloxyethyl)dimethylammonium cation exhibited notable biodegradability (63% after 28 days) and various toxicity classifications depending on the tested organism: category V towards rats with LC50 > 2000 mg, category II towards fish with LC50/96 h at 10.62 mg/L, category I towards algae and daphnids with ErC50/72 h at 1.73 mg/L and EC50 at 0.28 mg/L, accordingly. These findings provide evidence that synthesis of HILs with a specifically designed structure may be successfully employed for obtaining novel, efficient and environmentally friendly plant protection agents.
    New Journal of Chemistry 05/2015; 39(7). DOI:10.1039/C5NJ00609K · 3.16 Impact Factor
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    ABSTRACT: Ten sulfonylurea-based herbicidal ionic liquids (HILs) were prepared by combining the metsulfuron-methyl anion with various cation types including quaternary ammonium ([bis(2-hydroxyethyl)methyloleylammonium]+, [2-hydroxyethyltrimethylammonium]+), pyridinium ([1-dodecylpyridinium]+), piperidinium ([1-methyl-1-propylpiperidinium]+), imidazolium ([1-allyl-3-methylimidazolium]+, [1-butyl-3-methylimidazolium]+), pyrrolidinium ([1-butyl-1-methylpyrrolidinium]+), morpholinium ([4-decyl-4-methylmorpholinium]+) and phosphonium ([trihexyltetradecylphosphonium]+ and [tetrabutylphosphonium]+). Their herbicidal efficacy was studied in both greenhouse tests and field trials. Preliminary results for the greenhouse tests showed at least twice the activity for all HILs when compared to the activity of commercial Galmet 20 SG®, with HILs with phosphonium cations being the most effective. The results of two-year field studies showed significantly less enhancement of activity than observed in the greenhouse; nonetheless it was found that the herbicidal efficacy was higher than that of the commercial analog and efficacy varied depending on the plant species.
    Journal of Agricultural and Food Chemistry 03/2015; 63(13). DOI:10.1021/jf505782p · 3.11 Impact Factor
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    ABSTRACT: Tebuconazole and propiconazole were converted into salts by reaction with inorganic and organic acids. Numerous novel salts were obtained as a result, many of which could be characterized as protic ionic liquids. Their thermal stability and biological activity against fungal species Fusarium culmorum, Microdochium nivale, Sclerotinia sclerotiorum and Botrytis cinerea (in concentration range from 10 up to 1000 ppm) were assessed in the framework of this study. The evaluation revealed that high antifungal activity of the synthesized tebuconazole- and propiconazole-based salts, which may be classified as new triazole fungicides, was preserved. Physical properties of the obtained salts have changed significantly, thus creating new application possibilities of known triazole fungicides.
    RSC Advances 01/2015; 5(13). DOI:10.1039/C4RA12160K · 3.84 Impact Factor
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    ABSTRACT: Eight new glyphosate-based herbicidal ionic liquids (HILs), containing both mono- and dianions of glyphosate (benzalkonium glyphosate, bis(2-hydroxyethyl)cocomethylammonium glyphosate, oleylmethylbis(2-hydroxyethyl)ammonium glyphosate, didecyldimethylammonium glyphosate, di(hydrogenated tallow)dimethylammonium glyphosate, 4-decyl-4-ethylmorpholinium glyphosate, di(benzalkonium) glyphosate, and di(bis(2-hydroxyethyl)cocomethylammonium) glyphosate) were prepared via acid–base reaction between the corresponding ammonium hydroxides (some premade) and glyphosate free acid. The transformation of glyphosate free acid into ionic liquids led to an elimination of melting points in all but one compound and significant change in solubilities. All HILs exhibited higher thermal stability than glyphosate free acid. Greenhouse testing indicated that while at a higher application rate of 360 g/ha the efficacy of all the HILs was comparable to the commercial herbicide control, at a lower application rate of 180 g/ha, the efficacy of all HILs was as much as two and a half to three times higher when compared to the commercial formulation, and the dianionic glyphosates were the most effective. In field trials, all but one of the tested HILs demonstrated excellent efficacy. Laboratory regrowth tests established that the ionic liquids of glyphosate are efficiently translocated to rhizomes preventing the regrowth of plants.Keywords: Glyphosate; Roundup; Herbicidal ionic liquids; Efficacy; Greenhouse test; Field test; Regrowth
    ACS Sustainable Chemistry & Engineering 12/2014; 2(12):2845-2851. DOI:10.1021/sc500612y · 4.64 Impact Factor
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    ABSTRACT: Ionic liquids with dual pesticidal function were obtained using cheap, well known and commonly employed fungicides and herbicides. High activity was maintained for both the fungicide (cation) and the herbicide (anion). The obtained salts are novel phytopharmaceuticals, which may be successfully used as an alternative to conventional pesticides.
    RSC Advances 08/2014; 4(75). DOI:10.1039/C4RA04816D · 3.84 Impact Factor
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    ABSTRACT: Ammonium ionic liquids with the 4-chloro-2-methylphenoxyacetate anion were synthesized and characterized. Physicochemical properties, such as thermal stability, phase transition temperatures, viscosity, density, refractive index, as well as surface activity and herbicidal activity were determined. Improved physicochemical properties suggest a reduced environmental impact of newly formed group of herbicidal ionic liquids (HILs). HILs with a longer substituent can be characterized with better herbicidal activity in comparison with commercial products.
    Tetrahedron 08/2014; 70(32):4784-4789. DOI:10.1016/j.tet.2014.05.041 · 2.82 Impact Factor
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    ABSTRACT: Ammonium and piperidinium theophyllinate-based ILs were synthesized and characterized. Physicochemical properties, such as thermal stability, phase transition temperatures, viscosity, density, refractive index, as well as surface activity, feeding deterrence, antifungal activity and also biodegradability were determined. The synthesized theophyllinate-based ILs were surface active compounds. They exhibited insect-feeding deterrent activities. At the same time, the studied salts are also efficient fungicides and potential pesticidal ionic liquids. The obtained data suggest that certain structural modifications may increase their biodegradability in order to provide an environmentally friendly product.
    New Journal of Chemistry 06/2014; 38(7). DOI:10.1039/C4NJ00463A · 3.16 Impact Factor
  • Adam Morel · Anna M Trzeciak · Juliusz Pernak
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    ABSTRACT: Heck arylation of 2,3-dihydrofuran with iodobenzene was carried out in systems consisting of different palladium precursors (Pd2(dba)3, Pd(acac)2, PdCl2(cod), [PdCl(allyl)]2, PdCl2(PhCN)2, PdCl2(PPh3)2) and ionic liquids (CILs) with L-prolinate or L-lactate anions. All the tested CILs caused remarkable increases of the conversion values and in all of the reactions 2-phenyl-2,3-dihydrofuran (3) was obtained as the main product with a yield of up to 59.2%. The highest conversions of iodobenzene were achieved for the [PdCl(allyl)]2 precursor. Formation of Pd(0) nanoparticles, representing the resting state of the catalyst, was evidenced by TEM.
    Molecules 06/2014; 19(6):8402-8413. DOI:10.3390/molecules19068402 · 2.42 Impact Factor
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    ABSTRACT: The selective hydrogenation of cinnamaldehyde has been studied using palladium catalysts based on epoxy resin cured with ionic liquids. Characterization of palladium catalysts has involved the following methods: IR spectroscopy, X-ray photoelectron spectroscopy (XPS), AAS spectroscopy and time-of-flight secondary ion mass spectrometry (TOF-SIMS). The investigated catalysts showed high stability and good recycling efficiency what makes them useful for a prolonged use. The factors influencing the selectivity of the supported catalysts were discussed.
    Polish Journal of Chemical Technology 12/2013; 15(4). DOI:10.2478/pjct-2013-0063 · 0.44 Impact Factor
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    ABSTRACT: Plant growth regulator — 2-chloroethyltrimethylammonium chloride (CCC) was converted into ionic liquid in the metathesis reaction. New forms of CCC as ILs were stable in air as well in contact with water and organic solvents. The biological action of the cation (CCC) in ILs was preserved. Type of anion determined hydrophobicity and hydrophilicity of the whole molecule and it also influenced the biological activity of the plant growth regulator. All of the investigated salts retarded growth of winter wheat stems and most of them increased yield at the same time, when compared to control and standard 2-chloroethyltrimethylammonium chloride.
    Central European Journal of Chemistry 11/2013; 11(11). DOI:10.2478/s11532-013-0309-1 · 1.33 Impact Factor
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    ABSTRACT: Herbicidal ionic liquid with dual functions has been synthesized and characterized (properties, chemical stability and biological activity). 2-Chloroethyltrimethylammonium (4-chloro-2-methylphenoxy)acetate prepared in an alkaline environment undergoes the reaction of dehydrochlorination by the E2 mechanism. This may be described as a specific instance of providing third generation ILs with high potential of application, which preserve both pesticidal properties: the herbicidal activity due to their anions and plant growth inhibition effect due to their cations.
    Tetrahedron 09/2013; 69(38):8132–8136. DOI:10.1016/j.tet.2013.07.053 · 2.82 Impact Factor
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    ABSTRACT: Wychodząc z chlorku diallilodimetyloamoniowego otrzymano herbicydy poli(diallilodimetyloamoniowe), które okazały się nowymi herbicydowymi cieczami jonowymi. Opisano syntezę i aktywność herbicydową otrzymanych soli.
    Przemysl Chemiczny 09/2013; 92(9):1602-1605. · 0.37 Impact Factor
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    ABSTRACT: Palladium complexes of the type [IL](2)[PdCl4] (IL = imidazolium cation) were found to be very active catalysts for the Suzuki-Miyaura reaction of 2-bromotoluene with phenylboronic acid carried out in 2-propanol or 2-propanol/water at 40 degrees C using normal heating or microwaves as a heating source. In 2-propanol, the highest yields (89% and 85%) were obtained for [dmiop](2)[PdCl4] and [dmdim][PdCl4] (dmiop = 1,2-dimethy1-3-propoxymethyl imidazolium cation, dmdim =3,3'-[1,7-(2,6-dioxaheptane)]bis(1,2-dimethylimidazolium) cation) containing cations substituted at the C2 carbon with a methyl group. In the presence of water, all [IL](2)[PdCl4] complexes produced ca. 90% of 2-methylbiphenyl. Very good results were also obtained in the Suzuki-Miyaura reaction of different aryl bromides and chlorides. For example, the conversion of 2-chlorotoluene was 71% at 70 degrees C. During the catalytic reaction, the formation of Pd(0) nanoparticles was evidenced by TEM. Mechanistic studies, including Hg(0) tests, showed that Pd(0) nanoparticles acted as a source of catalytically active soluble palladium species.
    Applied Catalysis A General 09/2013; 466:216-223. DOI:10.1016/j.apcata.2013.06.046 · 3.67 Impact Factor
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    ABSTRACT: In this work, the application of an epoxy resin cured with ammonium ionic liquids as a support for palladium complex catalyst is reported. Supports based on epoxy resin were obtained as a result of the use of ionic liquids: didecyldimethylammonium tetrafluoroborate [d2m2am][BF4], 1-methyltheobromine tetrafluoroborate [mthb][BF4], didecyldimethylammonium theobrominate [d2m2am][thb], didecyldimethylammonium theophyllinate [d2m2am][thp] as cross-linking agents. The characterization of polymeric supports and heterogenized palladium catalysts has involved research methods like time-of-flight secondary ion mass spectrometry (TOF-SIMS), infrared spectroscopy (IR), scanning electron microscopy (SEM), X-ray photoelectron spectroscopy (XPS). The activity and stability during long-term use of the investigated catalytic systems were tested in a model Heck reaction. The influence of the type of ILs used as epoxy hardeners on the catalytic properties of epoxy-supported palladium catalysts is discussed.
    Comptes Rendus Chimie 08/2013; 16(8):752–760. DOI:10.1016/j.crci.2012.12.005 · 1.48 Impact Factor
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    ABSTRACT: New ILs containing the (2,4-dichlorophenoxy)acetate anion have been synthesized and characterized (properties, chemical and thermal stability, surface activity). Next, the possibility to use them as herbicides and plant growth regulators has been studied. The obtained ILs exhibited higher biological activity than the currently used herbicide (2,4-D salt) and plant growth regulator (CCC).
    Tetrahedron 06/2013; 69(23):4665–4669. DOI:10.1016/j.tet.2013.03.097 · 2.82 Impact Factor
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    ABSTRACT: Twenty eight new dicamba (3,6-dichloro-2-methoxybenzoic acid)-based herbicidal salts, have been synthesized and characterized in order to attempt to improve the efficacy of this widely known herbicide used to protect maize, grassland, and other cultures. The new compounds, most of which are ionic liquids by definition and three of which are solids melting above 100 degrees C, were prepared by pairing quaternary tetraalkyl-or alkoxyammonium, piperidinium, imidazolium, pyridinium, morpholinium, quinolinium, and phosphonium cations with the dicamba anion. Growth chamber and field test data suggested that ionic liquid forms of dicamba offer substantially increased efficacy which would allow less to be applied in the field. Compared to the commercial dicamba free acid product, improved physical properties were observed including higher decomposition temperatures and reduced volatilities, suggesting a potential reduction of overall environmental impact of this herbicide.
    Green Chemistry 06/2013; 15(8). DOI:10.1039/C3GC37143C · 6.85 Impact Factor
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    ABSTRACT: TiO2/N-cellulose nanocomposite wassuccessfully prepared in the (cyclohexyl)hexyldimethylammonium acetate–dimethyl sulfoxide solution. The obtained composite was characterized with various techniques like UV–Vis/DR, FTIR/DRS, X-ray diffraction, thermogravimetric analysis, DLS method and BET SSA measurements. TiO2/N-cellulose nanocomposite exhibited high UV–Vis light absorption with energy gap shifted to the visibleregion. Additive of TiO2/N photocatalyst to cellulose-IL-DMSO solution leads to obtaining the material with higher thermostability and limited photoactivity http://link.springer.com/article/10.1007/s10570-013-9906-6/fulltext.html
    Cellulose 06/2013; 20(3):1293-1300. DOI:10.1007/s10570-013-9906-6 · 3.03 Impact Factor
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    ABSTRACT: MCPA (4-chloro-2-methylphenoxy) acetic acid is a common synthetic auxin used as a herbicide. The purpose of this study was to determine the effects of four new forms of MCPA being the herbicidal ionic liquids (HILs) with MCPA as an anion and two previously known formulations (potassium–sodium salt and 2-ethylhexyl ester) on seed germination and seedling development of winter oilseed rape (Brassica napus). Rape plants are susceptible to MCPA and volunteers can be a big problem in crop rotation. Seedling fresh weight and root length were quantified, mitotic activity, as well as lipid, starch, hydrogen peroxide and polyphenol contents were assessed by light and fluorescence microscopy and the computer-aided cytophotometer. In primary roots mitotic activity was almost completely inhibited under the influence of herbicides, cell elongation zones and root hair zones were significantly reduced, and a characteristic bolded root segment formed just above a meristem. In contrast to the traditional salt formulation the new HILs were weak inducers of hydrogen peroxide synthesis, but were potent stimulators of the synthesis of phenolic compounds and storage as well as emergency substances such as lipids and starch. All tested forms of MCPA caused strong phytotoxic effect on winter rape seedlings, but the tested HILs were more effective.
    Acta Physiologiae Plantarum 03/2013; 36(3). DOI:10.1007/s11738-013-1448-x · 1.52 Impact Factor