Juliusz Pernak

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

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Publications (137)254.11 Total impact

  • [Show abstract] [Hide abstract]
    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; · 3.71 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. · 2.80 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). · 2.97 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 (Basel, Switzerland). 01/2014; 19(6):8402-8413.
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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). · 1.17 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.
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    ABSTRACT: Pairing quaternary tetraalkyl- or alkoxyammonium, piperidinium, imidazolium, pyridinium, morpholinium, quinolinium, and phosphonium cations with the dicamba anion leads to herbicidal salts with improved properties and increased efficacy compared to the commercial dicamba free acid.
    Green Chemistry 06/2013; · 6.83 Impact Factor
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    ABSTRACT: New quaternary ammonium salts containing unsaturated substituents (allyl or vinyl) were synthesized. All of them were subjected to spectroscopic, elemental and thermogravimetric analyses. The above compounds are ionic liquids (Tm < 100 °C) and were applied to immobilization of three rhodium(I) complexes [Rh(PPh3)3Cl], [{Rh(μ-Cl)(cod)}2] and [{Rh(μ-OSiMe3)(cod)}2] as well as three platinum complexes at different oxidation states [Pt(PPh3)4], K2[PtCl4] and K2[PtCl6]. Homogeneous catalytic systems were obtained and employed in the biphasic process of hydrosilylation of octene and allyl glycidyl ether with 1,1,1,3,5,5,5-heptamethyltrisiloxane. Catalytic activities of all the systems were compared and the best one was selected. The latter made it possible to recycle 10 times the same catalyst sample without a decrease in its activity and to easy separate the catalyst from the post-reaction mixture by decantation. The developed system is one of the most effective catalytic systems for hydrosilylation k
    Applied Catalysis A General 01/2013; 451:168-175. · 3.41 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 01/2013; 20:1293-1300. · 3.48 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 01/2013; · 1.31 Impact Factor
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    ABSTRACT: Chiral ionic liquids (CILs) containing l-prolinate and l-lactate anions and non-chiral quaternary ammonium cations were employed in the palladium catalyzed enantioselective Heck arylation of 2,3-dihydrofuran with aryl iodides (iodobenzene, 4-iodotoluene, 2-iodoanisole, 4-iodoanisole, 4-iodoacetophenone). In all the reactions 2-aryl-2,3-dihydrofuran () was obtained as the main product with the yield up to 52% at the total conversion reaching 83%. Product , 2-phenyl-2,3-dihydrofuran, was obtained with excellent enantioselectivity (>99% ee) in a 6 h reaction with tetrabutylammonium l-prolinate. In the proposed homogeneous reaction Pd(0) nanoparticles are considered as a resting state of the catalyst and a source of soluble palladium species catalyzing the Heck reaction. The yield and stereoselectivity of the Heck reaction are strongly influenced by the kind of non-chiral cations present in CILs.
    Dalton Transactions 11/2012; · 3.81 Impact Factor
  • Ref. No: PL212164, Year: 08/2012
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    ABSTRACT: We have synthesized alkyl(cyclohexyl)dimethylammonium bromides, formates and acetates, 2-methoxyacetates, 2-(2-methoxyethoxy)acetates, 2-[2-(2-methoxyethoxy)ethoxy]acetates, and 2-ethoxyacetates and assessed their ability to dissolve cellulose. Their physicochemical properties and microbiological activity were determined. Alkyl(cyclohexyl)dimethylammonium cation dimensions of alkyl groups are essential for cellulose solubility and are generally limited to butyl, hexyl, and octyl as effective substituents. In parallel, the alkyl group determines activity of the entire molecule against microbes. The molecule's biological activity against microbes begins when a length of the alkyl substituent begins to block cellulose solubility. We present the computational model of the solubility mechanism, composed of an ensemble of two cellobiose units and (cyclohexyl)hexyldimethylammonium acetate.
    RSC Advances 08/2012; 2(22):8429-8438. · 3.71 Impact Factor
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    ABSTRACT: Herbicidal ionic liquids (HILs) with a 2,4-D anion were synthesized and characterized. These salts have chemical and thermal stability. HILs exhibited higher biological activity than currently used salts of 2,4-D. HILs are nonvolatile and showed substantially lower water solubility than starting herbicides.
    Tetrahedron. 06/2012; 68(22):4267–4273.
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    ABSTRACT: The effect of seven morpholinium ionic liquids on the survival of Arion lusitanicus and A. rufus and damage to plants by those slugs. The pests was studied under laboratory conditions. It was found that these compounds were not lethal to the slugs. The slugs showed a different reaction to the compounds tested. The compounds [BMmorph][HSO4] and [C10OMmorph][Mig] reduced the plant damage caused by both slug species, whereas [BMmorph][MEEAc] stimulated grazing by A. lusitanicus. The compounds [BMmorph][MBT] and [DEmorph][H2PO4] reduced grazing by A. lusitanicus and stimulated grazing by A. rufus. The action of the tested morpholinium ionic liquids was of short duration. Therefore further research are needed to improve their durability of action.
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    ABSTRACT: Three herbicidal ionic liquids (HILs)—alkyldi(2-hydroxyethyl)methylammonium 2,4-dichlorophenoxy)acetate, dialkyldimethylammonium (2,4-dichlorophenoxy)acetate, and alkyltrimethylammonium (2,4-dichlorophenoxy)acetate—were synthesized and their activity against broad-leaved weeds was investigated under field conditions. HILs as [cation][2,4-D] used in winter wheat were much more active compared to 2,4-D-dimethylammonium salt and demonstrated efficacy similar to 2,4-D 2-ethylhexyl ester. HILs exhibited desirable surface properties such as low contact angle of droplets and low surface tension. Moreover, the HILs may be safer to operators and neighboring plants due to their nonvolatile nature. HILs at 450 g ha−1 of 2,4-D did not injure wheat.
    Weed Science 01/2012; 60(2):189-192. · 1.76 Impact Factor
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    ABSTRACT: A series of 4-benzyl-4-methylmorpholinium salts have been synthesized producing morpholinium ionic liquids with inorganic (chloride, nitrate, tetrafluoroborate, hydrogen sulphate) and organic (formate, acetate, methoxyacetate, 2-(2-methoxyethoxy)acetate, hexanoate, octanoate, dodecyl sulphate, 2-ethylbutyrate, lactate, crotonate, maleate, salicylate, saccharinate) anions. Their physicochemical properties, cytotoxicity to the promyelocytic leukaemia rat cell line IPC-81, oral toxicity and biodegradability were determined. The anion significantly determined the state of aggregation and cytotoxicity. The results enabled 4-benzyl-4-methylmorpholinium ionic liquids to be classified as being of moderate or low toxicity (EC50 between 0.15 and 14.13 mM). The acute toxicity for 4-benzyl-4-ethylmorpholinium acetate is between 300–2000 mg kg−1 b.w. in female rats. The activity of these morpholinium salts against bacteria and fungi was very low. It was found that new 4-benzyl-4-methylmorpholinium-based ionic liquids with anions commonly used for dissolving cellulose, such as formate or acetate, can also be used as new biomass solvents.
    Green Chemistry 01/2011; 13(10):2901-2910. · 6.83 Impact Factor
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    ABSTRACT: Pyrylium salts represent a new group of ionic liquids (ILs) containing a positive charge on the oxygen atom. The novel ILs were obtained starting with 4-pyrones from petroleum feedstock and renewable resources and sulfonic acids. The use of carboxylic acids instead of salts resulted in the formation of cocrystals. The synthesized pyrylium ionic liquids were stable in air and in contact with water and common organic solvents. The permanganate indices which are characteristic for prepared sulfonates were also investigated. The pyrylium ionic liquids were useful as immobilizers and dissolving agents in hydrosilylation reactions.
    Tetrahedron Letters - TETRAHEDRON LETT. 01/2011; 52(33):4342-4345.
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    ABSTRACT: Ionic liquids with herbicidal anions (named herbicidal ionic liquids—HILs) were synthesized and characterized. The combination of two active chemicals as the [cation][anion] form in a single moiety reduced the number of additional chemicals required per application. HILs ([cation][MCPA]) exhibited higher biological activity than currently used salts of MCPA, and involved pesticides of a multidirectional activity ([plant growth regulator][MCPA]). Acute toxicity of HILs could be controlled by appropriate selection of cation type. These salts had chemical and thermal stability, and showed substantially lower water solubility than starting herbicides, thus reducing soil and groundwater mobility.
    Tetrahedron. 01/2011; 67(26):4838-4844.
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    ABSTRACT: A group of quaternary ammonium mandelates and l-prolinates, as ionic liquids, were synthesized and characterized. The prepared salts were soluble in water and showed high surface activity. The described synthesis of l-prolinate was simple and the obtained ionic liquid contained a chiral anion. l-Prolinate in CH2Cl2 was employed for the asymmetric Michael addition of a ketone to nitrostyrene. A yield of 60%, enantioselectivity (upto 50% ee), and good diastereoselectivity (syn/anti ratio of up to 90:10) were obtained for the asymmetric addition of cyclohexanone. These novel ionic liquids proved to be very effective anti-microbial and anti-fungal agents, especially didecyldimethylammonium l-prolinate. Additionally, it was found that phytotoxicity can be a useful tool in assessing the optical forms of ionic liquids.
    Tetrahedron Letters - TETRAHEDRON LETT. 01/2011; 52(12):1325-1328.

Publication Stats

688 Citations
254.11 Total Impact Points


  • 1991–2014
    • Poznan University of Technology
      • • Division of Chemical Technology
      • • Faculty of Chemical Technology
      • • Institute of Chemical Technology and Engineering
      Posen, Greater Poland Voivodeship, Poland
  • 2012
    • Wyższa Szkoła Handlowa we Wrocławiu
      Vrotslav, Lower Silesian Voivodeship, Poland
  • 2010
    • Uniwersytet Medyczny im.Karola Marcinkowskiego w Poznaniu
      • Department of Toxicology
      Poznań, Greater Poland Voivodeship, Poland
  • 2003–2009
    • Poznan University of Medical Sciences
      • Department of Toxicology
      Poznań, Greater Poland Voivodeship, Poland
  • 2007
    • Institute of Industrial Organic Chemistry
      Warszawa, Masovian Voivodeship, Poland
  • 2004
    • Medical University of Gdansk
      • Department of Biopharmaceutics and Pharmacodynamics
      Gdańsk, Pomeranian Voivodeship, Poland
  • 1996
    • Adam Mickiewicz University
      • Department of Biochemistry
      Poznań, Greater Poland Voivodeship, Poland