Characterization of inclusion complexation between fenoxaprop-p-ethyl and cyclodextrin

Cyclodextrins (CDs) derived from natural starches are capable of forming inclusion complexes with a variety of organic compounds. This work evaluated the complexation role of CDs toward fenoxaprop-p-ethyl (FE) in an attempt to assess their potential as new formulation additives for more efficient FE delivery and better environmental approaches. beta-CD and its two derivatives, randomly methylated beta-CD (RAMEB) and 2-hydroxypropyl beta-CD (HP-beta-CD), were tested. The solubility of FE was enhanced in the presence of the CDs due to the formation of inclusion complexes, with RAMEB being >6 times more effective than the other two. The complexation was confirmed by differential scanning calorimetry (DSC), Fourier transform infrared spectroscopy (FTIR), and X-ray diffraction (XRD), where the FE melting peaks in DSC, the FTIR bands, and the XRD peaks were generally weakened. Within the tested time up to 60 min, the dissolution of the FE-CD complexes resulted in higher FE concentrations than did that of FE by itself. The dissolution of the FE-RAMEB complex was much faster than other complexes and FE alone. These results indicate that RAMEB was a better inclusion complexation agent for FE in terms of both solubility enhancement and dissolution rate. RAMEB may thus be used to improve FE delivery and to mobilize FE in soil for bioremediation.     

Complexation of several fungicides with beta-cyclodextrin: determination of the association constants and isolation of the solid complexes

The formation of inclusion complexes with beta-cyclodextrin was studied for several popular fungicides of different types: prochloraz, 2-phenylphenol, thiophanate methyl, 8-hydroxyquinoline, and benalaxyl. Phase solubility diagrams showed that in all cases complexation takes place, leading to an important increase of water solubility in prochloraz and benalaxyl. Equilibrium association constants could be determined from the phase solubility data and from NMR titrations in the case of 2-phenylphenol. Because of the low solubility of the complex formed between 8-hydroxyquinoline and beta-cyclodextrin, the corresponding association constant could not be determined. The solid complexes of fungicide-cyclodextrin were prepared and isolated by different methods. The isolation of real complexes and not physical mixtures was confirmed in the cases of prochloraz, 2-phenylphenol, and benalaxyl by differential scanning calorimetry.     

Solid inclusion complexes of vanillin with cyclodextrins: their formation, characterization, and high-temperature stability

This study reports the formation of solid vanillin/cyclodextrin inclusion complexes (vanillin/CD ICs) with the aim to enhance the thermal stability and sustained release of vanillin by inclusion complexation. The solid vanillin/CD ICs with three types of CDs (α-CD, β-CD, and γ-CD) were prepared using the freeze-drying method; in addition, a coprecipitation method was also used in the case of γ-CD. The presence of vanillin in CD ICs was confirmed by FTIR and (1)H NMR studies. Moreover, (1)H NMR study elucidated that the complexation stoichiometry for both vanillin/β-CD IC and vanillin/γ-CD IC was a 1:1 molar ratio, whereas it was 0.625:1 for vanillin/α-CD IC. XRD studies have shown channel-type arrangement for CD molecules, and no diffraction peak for free vanillin was observed for vanillin/β-CD IC and vanillin/γ-CD IC, indicating that complete inclusion complexation was successfully achieved for these CD ICs. In the case of vanillin/α-CD IC, the sample was mostly amorphous and some uncomplexed vanillin was present, suggesting that α-CD was not very effective for complexation with vanillin compared to β-CD and γ-CD. Furthermore, DSC studies for vanillin/β-CD IC and vanillin/γ-CD IC have shown no melting point for vanillin, elucidating the true complex formation, whereas a melting point for vanillin was recorded for vanillin/α-CD IC, confirming the presence of some uncomplexed vanillin in this sample. TGA thermograms indicated that thermal evaporation/degradation of vanillin occurred over a much higher temperature range (150-300 °C) for vanillin/CD ICs samples when compared to pure vanillin (80-200 °C) or vanillin/CD physical mixtures, signifying that the thermal stability of vanillin was increased due to the inclusion complexation with CDs. Moreover, headspace GC-MS analyses indicated that the release of vanillin was sustained at higher temperatures in the case of vanillin/CD ICs due to the inclusion complexation when compared to vanillin/CD physical mixtures. The amount of vanillin released with increasing temperature was lowest for vanillin/γ-CD IC and highest for vanillin/α-CD IC, suggesting that the strength of interaction between vanillin and the CD cavity was in the order γ-CD > β-CD > α-CD for solid vanillin/CD ICs.     

Encapsulation of quercetin and myricetin in cyclodextrins at acidic pH

The in vitro formation of quercetin- and myricetin-cyclodextrin inclusion complexes in acidic medium has been characterized using the enzymatic system horseradish peroxidase, which oxidizes those flavonols in the presence of H2O2. The presence of cyclodextrins (CDs) in the reaction medium inhibited flavonol oxidation due to the complexation of the flavonol in the hydrophobic cavity of CDs. This inhibitory effect depends on the complexation constant Kc between flavonol and the CD type used. The Kc for quercetin and myricetin with the different types of CD used was calculated by nonlinear regression of the inhibition curves obtained in the presence of CDs. In both cases (quercetin and myricetin), the Kc values obtained followed the order hydroxypropyl-beta-CDs > maltosyl-beta-CDs > beta-CDs, reflecting the greater affinity of modified cyclodextrins for the studied flavonols compared with their parental beta-CDs. Moreover, the complexation efficiency (CE) values for HP-beta-CDs and quercetin or myricetin were calculated (267.4 and 5.3, respectively), indicating that HP-beta-CDs are more efficient for the complexation of quercetin than myricetin in the studied conditions, despite of the K c values being very similar in both cases.     

Improvement of antifungal activity of 10-undecyn-1-ol by inclusion complexation with cyclodextrin derivatives

The inclusion complexation behavior between 10-undecyn-1-ol and cyclodextrin (CD) derivatives, namely, randomly methylated beta-CD (RM-beta-CD) and hydroxypropyl-beta-CD (HP-beta-CD), was studied in terms of solubility improvement, apparent stability constant, and the inclusion ratios of the resultant inclusion complexes. The aqueous solubility of 10-undecyn-1-ol was greatly improved through complexation with the CD derivatives. RM-beta-CD is comparatively more efficient in solubilizing 10-undecyn-1-ol with an apparent stability constant outstripping that of HP-beta-CD by about an order of magnitude. Comparative in vitro evaluations of the growth inhibition effects of inclusion complex solutions toward Rosellinia necatrix, a phytopathogenic fungus, were performed. In comparison with the positive control, appreciable improvements of the antifungal activity of 10-undecyn-1-ol through the addition of CD derivatives were observed visually. The improvement was evaluated in terms of area covered by the mycelia of Rosellinia necatrix and their growth rate. RM-beta-CD was proven to be more effective compared to HP-beta-CD with regard to the reduction of both fungal mycelium-covered area and growth rate constant, presumably owing to greater solubility enhancement by RM-beta-CD and thus the bioavailability of 10-undecyn-1-ol. Inclusion complexation of 10-undecyn-1-ol with CD derivatives suggests a potential means for production of an environmentally friendly 10-undecyn-1-ol-based fungicide to counteract R. necatrix.     

Water solubility of flavor compounds influences formation of flavor inclusion complexes from dispersed high-amylose maize starch

High-amylose maize starch, with and without native lipid, was used to make inclusion complexes with flavor compounds to investigate the effect of water solubility of flavor compounds on inclusion complex formation. Two pairs of terpenes, having high and low water solubility, were used. Aqueous starches were dispersed by heat before adding the flavor compound. The amounts of starch, native lipid, and flavor compound in precipitates were determined, and inferences about the physical state were made using data from X-ray diffraction and differential scanning calorimetry. The water solubility of the flavor compound was related to the extent of inclusion complexation. For the higher water solubility flavor compounds, starch yield and flavor entrapment were higher, producing precipitates with the V 7 pattern. Complex formation with the low-solubility flavor compounds was most effective in the presence of native lipid, producing precipitates with the V 6 pattern. The lipid in native high-amylose maize starch may enhance complexation with low-solubility compounds by forming ternary coinclusion complexes of starch-lipid-flavor.     

Preparation and characterization of the inclusion complex of chlorpyrifos in cyclodextrins to improve insecticide formulations

The chemical control of crops by organophosphate insecticide treatment is usually limited because the insecticides do not maintain their efficiency for long periods for several reasons, including environmental conditions or rapid degradation of the active ingredient. Chlorpyrifos is an organophosphate insecticide used worldwide to control a variety of soil insects and arthropods in a wide range of crops. It is easily soluble in organic solvents but shows poor water solubility. The inclusion of chrorpyrifos in cyclodextrins (CDs) improves its water solubility, bioavailability, and insecticidal activity and helps prevent overdosing, leading to more cost-effective and more environmentally friendly agricultural practices. Solubility studies of chlorpyrifos in the presence of different types of CDs show G2-beta-CDs to be the most effective CDs in the complexation process, giving 1:2 complexes, with complexation constant (Kc) values of 12.34 +/- 3.1 M(-1) for K1 and 3895 +/- 183 M(-1) for K2. These complexation constant values were corroborated by applying a fluorimetric method.     

Effect of Complexation Temperature on Thermal Properties and Enzymatic Hydrolysis of Starch–Oleic Acid Complexes

The effect of complexation temperature (30, 60, and 90°C) on the gelatinization properties, glass transition, enzymatic hydrolysis, and crystalline structure of high‐amylose corn starch–oleic acid (HACS‐OA) complexes created by a dimethyl sulfoxide (DMSO)‐based complexation method and of normal corn starch–oleic acid (NCS‐OA) complexes created by an alkaline‐based complexation method were investigated by using differential scanning calorimetry, thermogravimetric analysis, and X‐ray diffractometry. The results indicated that the highest complex indices were found in the complexes created at 30 and 60°C with the DMSO‐based complexation method and alkaline‐based complexation method, respectively. The X‐ray diffraction patterns of both HACS‐OA complexes and NCS‐OA complexes created at different complexation temperatures were the V‐type pattern. For the complexes created by the two methods, both the melting temperature and the glass transition temperature increased obviously with increasing complexation temperature. Complexation temperature also influenced the enzymatic hydrolysis rate of starch‐OA complexes.     

Preparation and characterization of inclusion complex of iprodione and beta-cyclodextrin to improve fungicidal activity

The effect of beta-cyclodextrin (beta-CD) on the improvement of the fungicidal activity of iprodione has been investigated. The inclusion complexation of beta-CD with iprodione has been prepared and characterized by integrating some analytical techniques (such as electrospray ionization-mass spectrometry, differential scanning calorimetry, thermogravimetry, x-ray diffraction, and scanning electron microscopy) and molecular simulation methods. The beta-CD/iprodione inclusion complex has exhibited different spectroscopic features and properties from iprodione. The stoichiometric ratio and stability constant describing the extent of formation of inclusion complexes have been determined by phase solubility studies. The calculated apparent stability constant of the iprodione/beta-CD complex was 407.5 M-1. The obtained inclusion complexes were found to significantly improve the water solubility of iprodione, and there is a 4.7-fold increase in the presence of 13 mM beta-CD as compared with the solubility of iprodione in deionized water in the absence of beta-CD. The bioassay demonstrated that the complex displayed over two-fold increase of the fungicidal activity. In addition, the possible structure of the beta-CD/iprodione complex was proposed according to the results of the molecular dynamic simulation. The present study provided useful information for a more rational application of iprodione, diminishing the use of organic solvents and increasing its efficacy.     

Interaction of fusarium mycotoxins, fusaproliferin and fumonisin B1, with DNA studied by electrospray ionization mass spectrometry

Electrospray ionization mass spectrometry (ESI-MS) in negative ion mode was used to monitor the possible noncovalent adduct formations between DNA analogue oligonucleotides and two Fusarium mycotoxins, fumonisin B1 and fusaproliferin. Using mild experimental ESI conditions specific noncovalent interactions were detected between both single- and double-stranded model oligonucleotides and fusaproliferin with 1:1 stoichiometry. Similar association complexes were observed for the deacetyl derivative of fusaproliferin. There were no peaks due to adduct formation present in the mass spectra of fumonisin B1, incubated with oligonucleotides in a wide concentration range, suggesting no specific interaction for this molecule. In a competitive complexation reaction, another mycotoxin, the beauvericin, forms more stable association complex with DNA than fusaproliferin. These findings can be of use in the understanding of molecular mechanisms of action during apoptosis and can be correlated with the teratogenic effect of fusaproliferin.     

Cyclodextrins as activator and inhibitor of latent banana pulp polyphenol oxidase

The effect of cyclodextrins (CDs) on o-diphenol oxidation catalyzed by banana polyphenol oxidase (PPO) was studied. The oxidation of dopamine, the natural substrate of banana, in the presence of cyclodextrins was unaffected, because this hydrophilic phenol does not form inclusion complexes with CDs. However, when a hydrophobic phenol such as tert-butylcatechol (TBC) was used, a marked inhibition was observed with beta-, hydroxypropyl-beta-, and maltosyl-beta- CDs. This inhibition was due to the complexation of TBC in the CD core, demonstrating that banana pulp PPO worked only toward free substrate and not toward the complex TBC-CDs. In addition, the effect of some inhibitors in the presence of CDs and dopamine as substrate was studied. Increasing concentrations of CDs, in the presence of two inhibitors (4-iodophenol and cinnamic acid) were able to activate the inhibited enzyme to reach the noninhibited level by complexing the inhibitors in the hydrophobic core of the CDs. This dual effect of CDs as activator and inhibitor was tested in crude banana pulp extracts, with surprising activation effects never before described being observed.     

Earthworms (Eisenia foetida, Savigny) mucus as complexing ligand for imidacloprid

Earthworms can excrete copious amounts of mucus that may affect the fraction, transport fate, and bioavailability of contaminants in soil. However, interaction of mucus with organic contaminants is still not well-known. In the present study, complexation properties of surface mucus (from the earthworm species Eisenia foetida, Savigny) with imidacloprid were investigated using fluorescence excitation emission matrix (EEM) spectroscopy. It was found that carbohydrates and proteins are major components in mucus of this species. Two fluorescent peaks belonging to protein-like substances were identified in the EEM spectrum of mucus. The protein-like fluorescence was clearly quenched by imidacloprid, indicating that the protein-like substances reacted strongly with imidacloprid. The fluorescence quenching processes was governed by a static process. The values of effective quenching constant (logK _a) for these two peaks were 11.46 and 7.96, respectively, indicating that there is a strong interaction between mucus and imidacloprid and mucus–imidacloprid complexes are formed. Higher binding constants (logK _b?=?25.6 and 14.0) than those for heavy metals binding to dissolved organic matter or organic pollutants binding to proteins confirm the strong complexation between mucus and imidacloprid. Our study implies that earthworm surface mucus may significantly affect the fraction, toxicity, and bioavailability of organic contaminants in the soil due to its high affinity for organic contaminants.     

Copper(II) complexes with refractory anionic surfactants found in sewage sludge

Electron spin resonance (ESR) spectrometry was used to study Cu(II) complexes with anionic surfactant compounds of the types that have been detected in sewage sludge or in the fulvic acid fraction of anaerobically-digested sewage sludge and found to resist biodegradation in the soil environment. The ESR spectra of frozen (77 °K), aqueous solutions of linear alkyl benzene sulfonates and fatty alcohol sulfate esters at Cu-ligand molar ratios ranging from 0.1 to 1 exhibited anisotropic patterns indicative of a d _x 2?y ² groundstate of Cu(II) bound into innersphere complexes with the ligands arranged in square planar coordination. Sulfonate-type surfactants, both in the acid and salt forms, appeared to complex Cu(II) more efficiently than ester sulfate-type surfactants. Conventional physical parameters calculated from the ESR spectra were consistent with fully oxygenated, 4 O-ligand binding sites for the Cu(II) ions and indicated the formation of similar unidentate or bidentate complexes between Cu(II) and the surfactants at any Cu/ligand molar ratio investigated. The spectral lineshapes and related parameters of the Cu(II)-anionic surfactant complexes, however, were not very similar to those observed previously for Cu(II)-sewage sludge FA complexes. It was concluded that anionic surfactants involved in Cu(II) complexation by sewage sludge or sewage sludge fulvic acid do not behave as isolated, independent ligands, but instead may participate as co-ligands with other O-containing functional groups and/or as moities incorporated into the fulvic acid structure.     

Influence of pH and soil copper on adsorption of metalaxyl and penconazole by the surface layer of vineyard soils

The upper horizons of old vineyard soils have substantial copper contents due to the traditional use of copper-based fungicides. Total copper levels in eight vineyard soils in the Rías Baixas area of Galicia (northwestern Spain) ranged from 60 to 560 mg kg(-1) (mean +/- SD = 206 +/- 170 mg kg(-1)). The adsorption of the fungicides metalaxyl (pK(a) = 1.41) and penconazole (pK(a) = 2.83) by these soils was determined using fungicide solutions of pH 2.5 and 5.5, and desorption of fungicide adsorbed at pH 5.5 was also determined. In all cases, Freundlich equations were fitted to the data with R (2) > 0.96. Penconazole was adsorbed and retained more strongly than metalaxyl, with K(F) values more than an order of magnitude greater. In the desorption experiments, both fungicides exhibited hysteresis. Soil copper content hardly affected the adsorption of metalaxyl, but K(F) values for adsorption of penconazole increased at a rate of about 0.1 mL(n) (microg of penconazole)(1-n) (microg of Cu)(-1), which is attributed to the formation of Cu(2+)-penconazole complexes with greater affinity for soil colloids than penconazole itself. Because the dependence of K(F) for penconazole adsorption on copper content was the same at both pH values, complex formation appears not to have been affected by the solubilization of 6-17% of soil copper at pH 2.5. A similar copper dependence, or lack of dependence, was observed when 100-1000 mg kg(-1) of copper was added as Cu(NO(3))(2).2H(2)O to the solutions from which the fungicides were adsorbed.     

Copper,Chromium, and Arsenic Adsorption and Equilibrium Modeling in An Iron-Oxide-Coated Sand,Background Electrolyte System

The adsorption of copper, chromate, and arsenate (CCA)onto iron-oxide-coated sand (IOCS) was examined insingle-metal and mixed-metal systems. Copper andarsenate were strongly adsorbed or formed inner-spheresurface complexes with the IOCS surface while chromatewas weakly adsorbed or formed an outer-sphere surfacecomplex with the IOCS surface. Copper adsorption byIOCS slightly increased in the presence of arsenatebut was not affected by the presence of chromate. Arsenate adsorption was not affected by the presenceof copper and/or chromate. Chromate adsorptionincreased in the presence of copper by the combinationof electrostatic effects and possiblesurface-copper-chromate ternary complex formation. The presence of arsenate significantly decreasedchromate adsorption due to competition for adsorptionsites and electrostatic effects. Using inner-spheresurface complexation constants for copper and arsenateand outer-sphere surface complexation constants forchromate, the triple-layer model (TLM) was successfulin describing adsorption of copper, chromate, andarsenate in single-solute systems. The modelindicated that each metal uses a different number ofadsorption sites. For CCA metals-IOCS systems, theequilibrium constants determined from single-solutesystems were not able to predict adsorption frommulti-solute systems. The TLM does not currentlyaccount for the heterogeneity of oxide surface sitesand the formation of ternary complexes and/or solidphases that do not exist in single-solute systems.     

Characterization and stability of transition metal complexes of chestnut (Castanea sativa L.) leaf litter

The water- and acid-insoluble fractions of a chestnut ( Castanea sativa L.) leaf litter sample and their complexes with Cu(II), Fe(III), and Mn(II) prepared in the laboratory were characterized by major elemental analysis, total Cu, Fe, and Mn content, infrared (IR), and electron spin resonance (ESR) spectroscopy. The IR spectra revealed a broad typology of functional groups (particularly carboxyls) in the solid litter, whereas the ESR spectra showed the existence of indigenous organic free radical species, inner-sphere Fe³⁺ complexes, and outer-sphere Mn²⁺ complexes. The litter exhibited a high residual binding capacity for Cu, Fe, and Mn in chemical forms of differing stability against water leaching and proton exchange. The ESR spectra of the metal complexes prepared in the laboratory indicated that Fe³⁺ and Cu²⁺ formed highly water-stable, inner-sphere complexes, whereas Mn²⁺ formed water-labile, outer-sphere complexes. Oxygen ligands of the litter were involved in metal complexation in all cases. The litter showed the highest affinity for Cu²⁺, followed by Fe³⁺ and Mn²⁺, when it was reacted with a single metal, whereas it complexed Fe³⁺ preferentially in the presence of both Cu²⁺ and Fe³⁺. Only a limited portion of the metal ions retained at the pH of distilled water remained bound in stable forms by the litter when the pH was lowered. Thus, variations of pH in forest soils will significantly affect micronutrient metal content and mobility in leaf litter.     

Sorption behavior of triazole fungicides in Indian soils and its correlation with soil properties

Adsorption-desorption of triazole fungicides, hexaconazole [2-(2,4-dichlorophenyl)-1-(1H-1,2,4,-triazol-1-yl) hexan-2-ol], triadimefon [1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl) butan-2-one], and penconazole[1-(2,4-dichloro-beta-propyl phenethyl)-1H-1,2,4-triazole] was studied in five Indian soils using batch method. The adsorption isotherms fitted very well to the Freundlich equation. Adsorption of various triazole fungicides increased in this order: triadimefon > hexaconazole > penconazole. The product of the Freundlich adsorption constants, K(f)(1/n), showed good correlation with the soil organic carbon (OC) content, suggesting that soil OC is the main controlling factor for triazoles adsorption. Clay and silt content of the soil also affected the adsorption constants. Adsorption of hexaconazole and triadimefon was nearly reversible in two low OC soils (soil 3, soil 5) where 90-100% of the sorbed fungicides was released in a single washing step. Otherwise, desorption of triazole fungicides showed hysteresis, and 30-60% of the triazole fungicides were retained by the soil after single washing. IR spectra showed that H-bonds and charge-transfer bonds between humic acid and fungicides probably operated as mechanisms of adsorption.     

Environmental effects of inclusion complexation between methylated beta-cyclodextrin and diclofop-methyl

Diclofop-methyl (DM) is a broad-spectrum herbicide but often shows a reduced biological activity against the target grasses due to its poor water solubility and slow translocation within plant tissues. Randomly methylated beta-cyclodextrin (MCD) is an effective inclusion complexation agent and, as a potential formulation additive, may thus improve the behavior of DM. We evaluated the complexing role of MCD by measuring the solubility and soil sorption of DM as a function of MCD concentration, as well as the dissolution rates of DM-MCD complexes. The complex was also extensively characterized by UV, fluorescence, Fourier transform infrared, nuclear magnetic resonance, and differential scanning calorimetry techniques. The apparent solubility of DM linearly increased with MCD concentration, indicating the formation of a 1:1 complex. In contrast, diclofop was not complexed by MCD. The DM-MCD complex appeared to have formed within the hydrophobic cavity of MCD. With the measured stability constant of 4740 L mol(-)(1), the complex was apparently stable, which resulted in DM resistant to hydrolysis, and hence the ratio of DM to the sum of DM and diclofop increased toward unity with increasing MCD concentration. The DM-MCD complex also quickly dissolved to a maximum within 5 min, due presumably to the hydrophilicity of MCD. The sorption of DM by soil was significantly reduced in the presence of MCD. All the results suggest that MCD may effectively improve the availability of DM to pests and for bioremediation.     

Inclusion complex of conjugated linoleic acid (CLA) with cyclodextrins

Conjugated linoleic acid (CLA) inclusion complexes with alpha-cyclodextrin (alpha-CD), beta-cyclodextrin (beta-CD), and gamma-cyclodextrin (gamma-CD) (designated CLA/CDs inclusion complexes) were prepared to determine the mole ratio of CLA complexed with CDs and the oxidative stability of CLA in the CLA/CDs inclusion complexes. When measured by GC, (1)H NMR, and T(1) value analyses, 1 mole of CLA was complexed with 5 mol of alpha-CD, 4 mol of beta-CD, and 2 mol of gamma-CD. The oxidation of CLA induced at 35 degrees C for 80 h was completely prevented by the formation of CLA/CDs inclusion complexes.     

Fluorescence of cereal flours.

Front-surface fluorescence spectra of cereal flours are easily measured with a commercial spectrofluorometer and a simple cell. The emission spectra are intense in the range 290-600 nm in which three emission bands are active. The most intense is due to the aromatic amino acid residues present in the proteins of flours. At least two other fluorophores are active in the above spectral range and compete for light with the chromophores present in the flours. Four absorption bands are revealed in the same spectral region by reflectance spectra, the most intense being due to the amino acidic fluorophores. Thus, the measured emission is the result of absorption, scattering, emission, and reabsorption processes. Information on the microenvironment of some fluorophores can be obtained. The possibility to recognize different species of cereals, even of different cultivars, is shown.