betadex and enilconazole

We report the control of imazalil (IMZ) antifungal activity utilizing its non-covalent assembly with β-cyclodextrins (β-CD) and cucurbit[8]uril (CB8) macrocycles, as well as its stimuli-responsive disassembly with cadaverine. The NMR results are consistent with inclusion of a single IMZ molecule inside the cavities of either CB8 from its aromatic site or β-CD from its aliphatic end. Efficient complex formation with both host molecules and controlled released upon the addition of cadaverine is supported by NMR measurements. The stimuli-responsiveness of the same host-guest assemblies with cadaverine was validated against seven economically important plant pathogenic fungi which cause agriculturally important plant diseases across the globe. While loading the drug into macrocycles cavities suppressed its activity, subsequent adding of cadaverine efficiently restored it up. The results in the present paper enable researchers working in the area of mycology and plant pathology to inhibit or reduce the fungal growth on demand in order to control these economically important plant pathogenic fungi.

Topics: beta-Cyclodextrins; Bridged-Ring Compounds; Cadaverine; Fungi; Imidazoles; Macromolecular Substances; Magnetic Resonance Spectroscopy; Molecular Structure; Plant Diseases

A scheme was demonstrated to elucidate the degradation behaviors of the two enantiomers of the fungicide imazalil in soil using cyclodextrin-modified capillary zone electrophoresis. The separation buffer was 50 mmol/L NaH2PO4, 5 mmol/L (NH4)H2PO4, and 5 mmol/L beta-cyclodextrin (pH 3.0). The limits of detection of this CE method were 0.24 and 0.26 microg/mL for (-)- and (+)-imazalil, respectively. Five different soil conditions were investigated in laboratory microcosms: under sunlight; in darkness; under UV irradiation; in sterilized soil; and in soil with wheat planted in it. Radiation, microorganisms, and uptake by wheat benefited the degradation of imazalil in this study. The half-lives (t1/2) of imazalil in soil under the above conditions were 20, 30.5, 11, 27.5, and 21.5 days, respectively. The degradation rate of imazalil in soil under the five different sets of conditions decreased in the order: UV irradiation > sunlight > soil with wheat planted in it > sterilized soil > soil kept in darkness. Imazalil in soil (pH 8.2, slightly alkaline) collected in the suburbs showed non-enantioselective degradation.

Topics: beta-Cyclodextrins; Biodegradation, Environmental; Darkness; Electrophoresis, Capillary; Imidazoles; Photochemistry; Soil; Soil Microbiology; Soil Pollutants; Stereoisomerism; Triticum; Ultraviolet Rays

An equimolar inclusion complex between imazalil, a selected fungicide, and beta-cyclodextrin using an aqueous standard solution procedure has been obtained. The complex has been investigated in solution by (1)H and (13)C NMR techniques in combination with computational methods in order to establish a valuable analytical protocol through which to gain insight into the interactions of the inclusion complex in aqueous solution. Intramolecular NMR distance constraints have been detected and used for three-dimensional complex structure determination.

Topics: beta-Cyclodextrins; Cyclodextrins; Fungicides, Industrial; Imidazoles; Magnetic Resonance Spectroscopy; Molecular Structure; Solutions; Water

Chiral resolution of imazalil, a fungicide, was performed by capillary electrophoresis (CE) using 2-hydroxypropyl-beta-cyclodextrin as a chiral selector. Factors affecting the chiral resolution and migration time of imazalil were studied. The optimum running conditions were found to be 5 mM ammonium dihydrogenphosphate-50 mM phosphate buffer (pH 3.0) containing 4 mM 2-hydroxypropyl-beta-cyclodextrin with an effective voltage of +25 kV at 20 degrees C using direct detection at 200 nm. Under these conditions, the resolution (Rs) of racemic imazalil was approximately 6. The extraction of imazalil from orange samples was done with acetonitrile under basic conditions. The extract was purified with a solid-phase extraction cartridge (Sep-Pak plus PS-2) and was analyzed by the above CE method. Eight orange samples were analyzed, and imazalil was detected in seven samples. In four of these seven oranges, the level of (-)-imazalil was the same as that of (+)-imazalil, but in the other three oranges, the level of (-)-imazalil was found to be lower than that of (+)-imazalil, suggesting that (-)-imazalil was degraded more quickly than (+)-imazalil in oranges.

Topics: 2-Hydroxypropyl-beta-cyclodextrin; beta-Cyclodextrins; Citrus sinensis; Cyclodextrins; Electrophoresis, Capillary; Fruit; Imidazoles; Indicators and Reagents; Stereoisomerism

An inclusion complex between imazalil (IMZ), a selected fungicide, and cyclomaltoheptaose (beta-cyclodextrin, betaCD) was obtained using supercritical fluid carbon dioxide. The best preparation conditions were determined, and the inclusion complex was investigated by means of 1H NMR spectroscopy in aqueous solution and 13C CPMAS NMR spectroscopy in the solid state. Information on the geometry of the betaCD/IMZ complex was obtained from ROESY spectroscopy, while the dynamics of the inclusion complex in the kilohertz range was obtained from the proton spin-lattice relaxation times in the rotating frame, T(1rho) (1H).

Topics: beta-Cyclodextrins; Carbon Dioxide; Carbon Isotopes; Cyclodextrins; Imidazoles; Magnetic Resonance Spectroscopy; Molecular Structure; Protons

A method for the inclusion of imazalil (IMZ) in the beta-cyclodextrin (betaCD), structural characterization of the inclusion complex and its antifungal activity against Penicillium digitatum and P. italicum assessed by in vitro and in vivo tests are reported. According to the starting stoichiometry of betaCD with respect to IMZ, an equimolar ratio beta-cyclodextrin-IMZ (betaCD-IMZ) was detected by (1)H NMR. In vitro assays showed that the freshly prepared betaCD-IMZ was as effective as IMZ, although 1- and 4-day-old betaCD-IMZ mixtures were more effective. Studies on Star Ruby grapefruit showed no significant differences in residue uptake between treatments with an IMZ commercially available fungicide (Deccozil) or betaCD-IMZ when equal active ingredient (a.i.) concentrations (250 mg/L) and dip temperatures (20 or 50 degrees C) were used. By contrast, treatments of Tarocco oranges and Di Massa lemons with 250 mg/L betaCD-IMZ at 50 degrees C produced significant differences in residue uptake in comparison with 250 mg/L Deccozil treatments at 50 degrees C. The a.i. degradation rate in grapefruit during postquarantine and simulated marketing period (SMP) at 20 degrees C was not affected by the type of formulation used, whether at 20 or 50 degrees C. Conversely, IMZ in oranges and lemons had greater persistence when applied at 50 degrees C. All fungicide treatments showed a comparable efficacy against decay in grapefruit and oranges, whereas treatment in lemons at 250 mg/L a.i. of heated fungicides had higher suppressive effects against decay than unheated chemicals having equal a.i. concentrations and comparable activity at 1200 mg/L IMZ at 20 degrees C.

Topics: beta-Cyclodextrins; Citrus; Cyclodextrins; Food Preservation; Fruit; Fungicides, Industrial; Hot Temperature; Imidazoles; Magnetic Resonance Spectroscopy; Penicillium