Chloramine Research Articles

Oxidation of tricyclic antidepressant drugs with chloramine-T in acidic solutions: kinetic, mechanistic and thermodynamic studies

The kinetics of the oxidation of two tricyclic antidepressants (TCA) namely, imipramine (IMP) and clomipramine (CLM) with sodium N-chloro-p-toluenesulfonamide or chloramine-T (CAT) in HClO4 medium was studied at 300 K. The two reactions followed identical kinetics with a first-order dependence of rate on [CAT]o and fractional order dependence on [TCA]o. The reaction is catalyzed by H+ ions with a fractional order dependence. The reaction was studied at different temperatures and activation parameters were evaluated. The reaction constants involved in the mechanism were computed. The solvent isotope effect was studied using D2O. Addition of p-toluenesulfonamide retards the reaction rate. The rate increased with decreasing dielectric constant of the medium. Variation of ionic strength of the medium and addition of halide ions (Cl- or Br-) showed no effect on the rate. The stoichiometry of the reaction was found to be 1:1 and the oxidation products were identified as imipramine-5-N-oxide and clomipramine-5-N-oxide. The rate of oxidation of IMP is faster than CLM. The observed results have been explained in terms of a mechanism and a relevant rate law has been deduced.

Mechanistic aspects for the oxidation of brilliant green dye by chloramine-T in the presence of perchloric acid: a spectrophotometric kinetic approach

The kinetics of a triarylmethane dye, brilliant green (BG), by sodium N-chloro-p-toluenesulfonamide or chloramine-T (CAT) was studied spectrophotometrically in HClO4 media at 303 K. Under identical experimental conditions, the rate law was −d [BG]/dt = k [BG] [H+]. Variations in ionic strength (μ) of the medium had no effect on the oxidation velocity. Addition of p-toluenesulfonamide, the reduction product of CAT and Cl−, had no significant effect on the rate of reaction. The values of rate constants observed at five different temperatures (298, 303, 308, 313, and 318 K) were utilized to calculate the activation parameters. The observed results have been explained by a general mechanism and the related rate law has been obtained. The process demonstrated in this study is cost effective, which holds great promise in potential application for pollutant control.

Variability of chlorination by-product occurrence in water of indoor and outdoor swimming pools

Swimming is one of the most popular aquatic activities. Just like natural water, public pool water may contain microbiological and chemical contaminants. The purpose of this study was to study the presence of chemical contaminants in swimming pools, in particular the presence of disinfection by-products (DBPs) such as trihalomethanes (THMs), haloacetic acids (HAAs) and inorganic chloramines (CAMi). Fifty-four outdoor and indoor swimming pools were investigated over a period of one year (monthly or bi-weekly sampling, according to the type of pool) for the occurrence of DBPs. The results showed that DBP levels in swimming pools were greater than DBP levels found in drinking water, especially for HAAs. Measured concentrations of THMs (97.9 vs 63.7 μg/L in average) and HAAs (807.6 vs 412.9 μg/L in average) were higher in outdoor pools, whereas measured concentrations of CAMi (0.1 vs 0.8 mg/L in average) were higher in indoor pools. Moreover, outdoor pools with heated water contained more DBPs than unheated pools. Finally, there was significant variability in tTHM, HAA9 and CAMi levels in pools supplied by the same municipal drinking water network, suggesting that individual pool characteristics (number of swimmers) and management strategies play a major role in DBP formation.

Investigation of chlorine decay of water resource in khanbebein city, Golestan, Iran

Aims: The object of the study was to identify chlorine demand factorsin water and chlorine in Kanbebein City water and eliminating of them. Materials and Methods: Concentration of free and combined residual chlorine with the methods presented in the book Standard Methods for Water and Wastewater Examination were measured. Other parameters such as: Temperature, TOC, TDS, pH, EC, nitrate, ammonia, total hardness, alkalinity, iron and manganese were also examined before and after of chlorination. Results: The Highest chlorine decay constant in the short time were in water well was 0.895 mgL -1 h -1 and the least amount of it was 0.0097 mgL -1 h -1 and the Highest chlorine decay constant in the long time were in water well was-0.092Lmg -1 h -1 and the least amount of it was-0.0017 Lmg -1 h -1 that correlated with nitrite, ammonia and iron concentration. Conclusion: The factors that affected short-time chlorine decay constant (k 2 ) were nitrite, ammonia and iron and The factors that affected on long-time chlorine decay constant (k 2 ) were Nitrite, ammonia and iron. The material removal techniques for them were the use of natural resins, zeolite, ion exchange, membrane and aeration methods, oxidation and sedimentation, and filtration.

Photolytic removal of DBPs by medium pressure UV in swimming pool water

Medium pressure UV is used for controlling the concentration of combined chlorine (chloramines) in many public swimming pools. Little is known about the fate of other disinfection by-products (DBPs) in UV treatment. Photolysis by medium pressure UV treatment was investigated for 12 DBPs reported to be found in swimming pool water: chloroform, bromodichloromethane, dibromochloromethane, bromoform, dichloroacetonitrile, bromochloroacetonitrile, dibromoacetronitrile, trichloroacetonitrile, trichloronitromethane, dichloropropanone, trichloropropanone, and chloral hydrate. First order photolysis constants ranged 26-fold from 0.020min−1 for chloroform to 0.523min−1 for trichloronitromethane. The rate constants generally increased with bromine substitution.Using the UV removal of combined chlorine as an actinometer, the rate constants were recalculated to actual treatment doses of UV applied in a swimming pool. In an investigated public pool the UV dose was equivalent to an applied electrical energy of 1.34kWhm−3d−1 and the UV dose required to removed 90% of trichloronitromethane was 0.4kWhm−3d−1, while 2.6kWhm−3d−1 was required for chloral hydrate and the bromine containing haloacetonitriles and trihalomethanes ranged from 0.6 to 3.1kWhm−3d−1. It was predicted thus that a beneficial side-effect of applying UV for removing combined chlorine from the pool water could be a significant removal of trichloronitromethane, chloral hydrate and the bromine containing haloacetonitriles and trihalomethanes.

Formation of haloacetic acids from dissolved organic matter fractions during chloramination

The objective of this study was to investigate the roles of dissolved organic matter (DOM) fractions, pH and bromide concentration in the formation of haloacetic acids (HAA) during chloramination. DOM from two surface waters with a low (2.9 L/mg-m) and high (5.1 L/mg-m) specific UV absorbance (SUVA254) values was isolated and fractionated into three fractions based on the hydrophobicity [i.e., hydrophobic (HPO), transphilic (TPH) and hydrophilic (HPI)]. DOM mass balances and DBP reactivity checks were performed to characterize the effects of isolation and fractionation steps. The fractions were chloraminated at three pHs and three bromide concentrations. The results showed that pH was the most important factor controlling HAA formation and speciation. The HAA yields significantly decreased with increase in pH from 6.3 to 9.0. The impact of bromide in the formation of brominated HAA species also became less important with increasing pH, and no brominated specie was detectable at pH 9. HPO fractions of the two source waters consistently showed higher HAA yields than TPH and HPI fractions. On the other hand, HPI fractions showed higher bromine incorporation than HPO and TPH fractions. To maintain higher and relatively stable combined chlorine residuals while reducing HAA formation, water utilities may consider keeping pH above 7.5 as one strategy. This will also lower the formation of brominated HAA species which have been shown to be more cyto- and geno-toxic than their chlorinated analogs.

유리염소 측정을 위한 일회용 스트립 센서

수질 분석에서 염소 소독제 잔류량 측정은 세균학적 안전성 확보와 염소의 과다 주입을 억제하기 위한 수단으로 매우 중요한 의미를 갖는다. 이러한 휴대용 잔류염소 측정기 개발을 위한 일회용 유리염소 스트립 센서를 스크린 프린팅 기술을 이용한 탄소 전극으로 제작하였다. 탄소 전극은 금과 백금 전극에 비해 결합염소(특히 <TEX>$NH_2Cl$</TEX>) 방해종에 대한 영향이 적었으며, -0.3 V(vs. Ag/AgCl) 인가전위에서 유리염소에 대해 안정한 감응성을 나타냈다. 이렇게 제작된 탄소 전극에 모세관현상으로 일정량의 시료를 재현성 있게 도입할 수 있는 유로구조를 갖는 일회용 스트립센서로 제작하였고, 잔류 유리염소의 분석에 적용하였다. The measurement of residual chlorine as a disinfectant is very important to ensure the safety against the pathogenic microbes and to suppress injection. The portable free chlorine sensor was fabricated with a disposable strip format by a screen printing method. The strip sensors prepared with a carbon-Ag/AgCl(cathode-anode) combination exhibited less interfering responses towards combined chlorine species(especially <TEX>$NHCl_2$</TEX>) and oxygen than the sensors prepared with other metals(i.e., gold and platinum). Free chlorine was determined chronoamperometrically with carbon-based electrodes at an applied potential of -0.3 V(vs. Ag/AgCl). A channel was built on the strip-type electrode for easy sampling, and the resulting strip sensors were employed to determine the concentrations of residual free chlorine.

Kinetic and Mechanistic Studies of Oxidation of an Antiallergic Drug with Bromamine-T in Acid and Alkaline Media

Cetrizine dihydrochloride (CTZH) is widely used as an anti-allergic drug. Sodium N-bromo-p-toluenesulfonamide or bromamine-T (BAT) is the bromine analogue of chloramine-T (CAT) and is found to be a better oxidizing agent than CAT. In the present research, the kinetics of oxidation of CTZH with BAT in acid and alkaline media was studied at 313 K. The experimental rate laws obtained are: -d[BAT]/dt= in acid medium and -d[BAT]/dt= in alkaline medium where PTS is p-toluenesulfonamide. Activation parameters and reaction constants were evaluated. The solvent isotope effect was studied using . The dielectric effect is positive. The stoichiometry of the reaction was found to be 1:1 and the oxidation products were identified as 4-chlorobenzophenone and (2-piperazin-1-yl-ethoxy)-acetic acid in both media. The rate of oxidation of CTZH is faster in acid medium. Suitable mechanisms and related rate laws have been worked out.

Dual Carbon–Chlorine Stable Isotope Investigation of Sources and Fate of Chlorinated Ethenes in Contaminated Groundwater

Chlorinated ethenes (CEs) are ubiquitous groundwater contaminants, yet there remains a need for a method to efficiently monitor their in situ degradation. We report here the first field application of combined stable carbon and chlorine isotope analysis of tetrachloroethene (PCE) and trichloroethene (TCE) to investigate their biodegradation in a heavily contaminated aquifer. The two-dimensional Compound Specific Isotope Analysis (2D-CSIA) approach was facilitated by a recently developed gas chromatography-quadrupole mass spectrometry (GCqMS) method for δ(37)Cl determination. Both C and Cl isotopes showed evidence of ongoing PCE transformation. Applying published C isotope enrichment factors (ε(C)) enabled evaluation of the extent of in situ PCE degradation (11-78%). We interpreted C and Cl isotopes using a numerical reactive transport model along a 60-m flow path. It revealed that combined PCE and TCE mass load was dechlorinated by less than 10%, and that cis-dichloroethene was not further dechlorinated. Furthermore, the 2D-CSIA approach allowed estimation of Cl isotope enrichment factors ε(Cl) (-7.8 to -0.8‰) and characteristic ε(Cl)/ε(C) values (0.42-1.12) for reductive PCE dechlorination at this field site. This investigation demonstrates the benefit of 2D-CSIA to assess in situ degradation of CEs and the applicability of Cl isotope fractionation to evaluate PCE and TCE dechlorination.

Sensitive and selective methods for determination of antipsychotic drug olanzapine in pharmaceuticals

Two simple and sensitive spectrophotometric methods have been developed for analysis of the antipsychotic drug olanzapine in pharmaceuticals. Method A is based on liberation of iodine by reaction between the drug and potassium iodate, followed by reaction with leuco crystal violet (LCV), the color of oxidized LCV being measured at 598 nm. Method B is based on oxidation of olanzapine with chloramine-T (CAT) in acidic medium, the unconsumed CAT being determined with rhodamine B, measuring the absorbance at 550 nm. Calibration graphs were linear over the ranges of 0.05–2.0 and 0.1–1.6 μg mL−1 olanzapine for method A and B, respectively. The molar absorptivity, Sandell’s sensitivity, detection limit, and quantitation limit were found to be 1.59 × 105, 0.00132, 0.038, and 0.117, respectively, for method A and 0.953 × 105, 0.00221, 0.064, and 0.192, respectively, for method B. The optimum conditions and other analytical parameters were evaluated. The proposed methods have been applied successfully for analysis of olanzapine in pure form and its dosage forms, and no interference was observed from common excipients present in pharmaceutical formulations.

Microbial Community Dynamics of an Urban Drinking Water Distribution System Subjected to Phases of Chloramination and Chlorination Treatments

Water utilities in parts of the U.S. control microbial regrowth in drinking water distribution systems (DWDS) by alternating postdisinfection methods between chlorination and chloramination. To examine how this strategy influences drinking water microbial communities, an urban DWDS (population ≅ 40,000) with groundwater as the source water was studied for approximately 2 years. Water samples were collected at five locations in the network at different seasons and analyzed for their chemical and physical characteristics and for their microbial community composition and structure by examining the 16S rRNA gene via terminal restriction fragment length polymorphism and DNA pyrosequencing technology. Nonmetric multidimension scaling and canonical correspondence analysis of microbial community profiles could explain >57% of the variation. Clustering of samples based on disinfection types (free chlorine versus combined chlorine) and sampling time was observed to correlate to the shifts in microbial communities. Sampling location and water age (<21.2 h) had no apparent effects on the microbial compositions of samples from most time points. Microbial community analysis revealed that among major core populations, Cyanobacteria, Methylobacteriaceae, Sphingomonadaceae, and Xanthomonadaceae were more abundant in chlorinated water, and Methylophilaceae, Methylococcaceae, and Pseudomonadaceae were more abundant in chloraminated water. No correlation was observed with minor populations that were detected frequently (<0.1% of total pyrosequences), which were likely present in source water and survived through the treatment process. Transient microbial populations including Flavobacteriaceae and Clostridiaceae were also observed. Overall, reversible shifts in microbial communities were especially pronounced with chloramination, suggesting stronger selection of microbial populations from chloramines than chlorine.

Occurrence and Spatial and Temporal Variations of Disinfection By-Products in the Water and Air of Two Indoor Swimming Pools

In order to improve disinfection by-product (DBP) exposure assessment, this study was designed to document both water and air levels of these chemical contaminants in two indoor swimming pools and to analyze their within-day and day-to-day variations in both of them. Intensive sampling was carried out during two one-week campaigns to measure trihalomethanes (THMs) and chloramines (CAMs) in water and air, and haloacetic acids (HAAs) in water several times daily. Water samples were systematically collected at three locations in each pool and air samples were collected at various heights around the pool and in other rooms (e.g., changing room) in the buildings. In addition, the ability of various models to predict air concentrations from water was tested using this database. No clear trends, but actual variations of contamination levels, appeared for both water and air according to the sampling locations and times. Likewise, the available models resulted in realistic but imprecise estimates of air contamination levels from water. This study supports the recommendation that suitable minimal air and water sampling should be carried out in swimming pools to assess exposure to DBPs.

Radioiodination and bioevaluation of nitrofurantoin for urinary tract imaging

Nitrofurantoin (NF) was labeled with iodine-125 via electrophilic substitution reaction. Some factors affecting the radiochemical yield of 125I-NF, such as NF concentration, chloramine-T (CAT) concentration, pH of the reaction mixture, reaction time, temperature, and reaction medium, were studied. The maximum yield of 125I-NF (90%) was obtained by using 3.7 MBq of Na125I, 1 mM CAT, 1 mM NF in DMF, at pH 2 and 60 °C within 5 min. The specific activity of 125I-NF reaches 33.3 MBq/0.2 mmol, and the 125I-NF was completely separated and purified by means of high pressure liquid chromatography. The biological distribution in normal mice indicates the suitability of radioiodinated NF for urinary tract imaging. Copyright © 2012 John Wiley & Sons, Ltd.

Tackling the issue of environmental survival of live Salmonella Typhimurium vaccines: Deletion of the lon gene

Vaccination is an important measure to control Salmonella contamination in the meat production chain. A previous study showed that both the ΔrfaJ and ΔrfaL strains are suitable markers and allow serological differentiation of infected and vaccinated animals. The aim of this study was to verify whether deletion of the lon gene in a Salmonella Typhimurium ΔrfaJ marker strain resulted in decreased environmental survival. Our results indicate that deletion of the lon gene in the ΔrfaJ strain did not affect invasiveness in IPEC-J2 cells and resulted in an increased susceptibility to UV, disinfectants (such as hydrogen peroxide and tosylchloramide sodium) and citric acid. Immunization of pigs with inactivated ΔrfaJ or ΔlonΔrfaJ vaccines allowed differentiation of infected and vaccinated pigs. Furthermore, deletion of the lon gene did not reduce the protection conferred by live wild type or ΔrfaJ vaccines against subsequent challenge with a virulent Salmonella Typhimurium strain in BALB/c mice. Based on our results in mice, we conclude that deletion of lon in ΔrfaJ contributes to environmental safety of the ΔrfaJ DIVA strain.

Kinetics and Mechanistic Investigation of Decarboxylation for the Oxidation of Levofloxacin by Chloroamine-T in Acidic Medium

The mechanistic investigation of oxidation of levofloxacin (LF) has been studied by chloramine-T(CAT) in aqueous perchloric acid medium at 25 °C. The reaction followed first-order kinetics with respect to [CAT], [LF], and [H+] in their lower concentrations range, tending to zero-order at their higher concentrations. First-order kinetics with respect to [CAT] was observed for the oxidation of levofloxacin. An increase in perchloric acid concentration increased the rate of reaction. The effect of added products, ionic strength, and dielectric constant of the medium was studied on the rate of reaction. The main products were identified by spot test, FT-IR, and NMR. A mechanism was proposed on the basis of experimental results. The activation parameters with respect to the slow step of the mechanism was evaluated, and the thermodynamic parameters were also determined and discussed.

What Happens When Chloramines and Chlorine Meet?

The growing use of chloramines as a secondary disinfectant has created a significant need for training and regulatory review at the state level. This need is even greater when a system using chloramines interconnects with other systems. As more communities consider interconnections with larger water systems, more combined (chlorine and chloramines) systems can be expected. Distribution system blending and mixing probably won't be the first choice of operational control when an interconnection is planned. However, blending or mixing may be the least expensive option.

Assessment of Occupational and Public Exposure to Trichloramine in Swiss Indoor Swimming Pools: A Proposal for an Occupational Exposure Limit

The presence of trichloramine in the air in different indoor swimming pools has been studied in several countries. In almost all studies, the results show a possible health impact due to trichloramine among pool attendants. The main objectives of our study were to evaluate, for the first time in Switzerland, occupational and public trichloramine exposure in a representative panel of indoor pools and to propose an occupational exposure limit for trichloramine. Measurements were done in 30 indoor swimming pools located in three regions of Switzerland: Jura, Neuchâtel, and Fribourg. All investigations were performed during the 2007-2008 winter season in order to assure closed windows and standard ventilation conditions. Trichloramine air samplings were performed at 130 cm above the floor around the pool. Analyses of free chlorine and bounded chlorine were performed on-site, and water samples were immediately sent to the laboratory for analysis of trihalomethanes, urea, and dissolved organic carbon. A health questionnaire was distributed to all the participants. Our results indicate that in all the studied facilities except one, the trichloramine concentrations were below the French reference value of 0.5 mg m(-3), and only three were equal to or slightly over 0.3 mg m(-3). Overall, our results point out a very low and consistent range of trichloramine concentrations (mean concentration of trichloramine: 0.114 ± 0.043 mg m(-3)). A total of 184 questionnaires were filled out by pool workers. Of the study population, 66% were men (n = 117), 21% were smokers (9 women and 29 men), and only 7% (n = 13) were ex-smokers. The control group was composed of 71 persons (38 men and 33 women); 22% (n = 15) were smokers and 24% (n = 16) ex-smokers. Our results demonstrate an increasing risk of irritative symptoms up to a level of 0.2-0.3 mg m(-3) of trichloramine. The health data in our study, as well as the review of the literature, strongly suggest fixing the trichloramine occupational exposure limit at 0.3 mg m(-3). Severe technical standards (on flocculation, filters, water flow, and ventilation systems) and regulations on water quality (free and combined chlorine, urea, and amount of fresh water) contribute to reducing trichloramine formation and, consequently, occupational and public trichloramine exposure. In addition, to ensure good public hygiene (showering before swimming), correct and regular public awareness campaigns should be undertaken.

Comparison of cytokine profiles in bronchoalveolar lavage fluid of mice exposed to respiratory and contact sensitizers

Respiratory sensitization to certain low molecular weight chemicals is a big concern for workers, but unfortunately there are no validated animal models to allow identification of sensitizing chemicals in the environment. In the present study, dermally sensitized and intratracheally challenged mice were used to investigate effective indicators of respiratory sensitizers. Changes in levels of total serum IgE and nine cytokines (G-CSF, IL-4, IL-5, IL-6, IL-12(p70), IL-13, IFN-γ, MCP-1 and TNF-α) in bronchoalveolar lavage fluid (BALF) were analyzed in BALB/c mice exposed to respiratory sensitizers (phthalic anhydride (PA); diphenylmethane-4,4'-diisocyanate (MDI); toluene diisocyanate (TDI); chloramine-T (CH); and piperazine (PI)) or contact sensitizers (2,4-dinitrochlorobenzene (DNCB); and oxazolone (OXA)). Non-sensitized mice were treated dermally with solvents and challenged intratracheally with the respective test chemicals as solvent controls. Increases in total serum IgE levels were observed in all treated mice, with apparent differences in cytokine profiles. PA caused statistically significant increases in Th2 cytokines, IL-4, IL-5 and IL-13, compared with the control. IL-5 was also found to be increased with CH. The other three respiratory sensitizers caused statistically significant increases in IL-13. In contrast, no change was apparent with contact sensitizers, DNCB and OXA, in these Th2 cytokines. Increases in the Th2 cytokines indicate that all five respiratory sensitizers induced immune responses in lungs. Interestingly, elevation of G-CSF levels in BALF appeared with all five respiratory sensitizers but not the two contact sensitizers. The findings suggest that G-CSF could be effective to identify respiratory sensitizers in animal models.

β-Cyclodextrin catalyzed oxidation of some α-amino acids with chloramine-T in alkaline medium: Kinetics and mechanistic studies

The kinetics of oxidation of α-amino acids (AAs) by chloramine-T (CAT) using β-cyclodextrin (BCD) as catalyst was studied in aqueous sodium hydroxide medium at 313 K. The kinetics of reactions was fractional-order with respect to [amino acids] and [β-cyclodextrin]. First-order with respect to [chloramine-T] and inverse fractional-order with respect to [OH −] have been found. Effect of ionic strength, added salt and reaction product (PTS) had no effect on reaction rate. The dependence of the reaction rate on temperature was studied and activation parameters were computed from Arrhenius–Eyring plots. The reaction mechanism and the derived rate law are consistent with the observed experimental results.

Síntesis y evaluación “in vitro” de la actividad antifúngica de oximas, éteres de oxima e isoxazoles

&lt;p&gt;&lt;strong&gt;&lt;/strong&gt;&lt;strong&gt;Objective&lt;/strong&gt;. To synthesize and carry out a preliminary evaluation of the &lt;em&gt;in vitro&lt;/em&gt; antifungal activity of oximes, oxime ethers and isoxazoles. &lt;strong&gt;Materials and methods&lt;/strong&gt;. Oximes were synthesized from aldehydes or ketones with NH&lt;sub&gt;2&lt;/sub&gt;OH.HCl and K&lt;sub&gt;2&lt;/sub&gt;CO&lt;sub&gt;3&lt;/sub&gt;. Oxime ethers were prepared by alkylation of oximes with propargyl bromide or 2-bromobenzyl bromide, using NaOH as base and acetone as solvent. The isoxazoles were obtained by 1,3-dipolar cycloadditions using ceric ammonium nitrate (CAN), chloramine T (CAT) and NaOCl. Products were identified or characterized using nuclear magnetic resonance (NMR) and mass spectrometry (MS). Radial growth inhibition assays against &lt;em&gt;Aspergillus niger&lt;/em&gt; and &lt;em&gt;Fusarium roseum&lt;/em&gt; were carried out. &lt;strong&gt;Results&lt;/strong&gt;. Five oximes, seven oxime ethers, four of them new, and four new isoxazoles were obtained. The assessed substances exhibited antifungal activity in amounts of 1,5 mg and 3,0 mg. &lt;strong&gt;Conclusions&lt;/strong&gt;. Although 1,3-dipolar cycloadditions allowed to obtain the desired isoxazoles, this methodology produced a wide variety of side products that reduced yields and made difficult the purification of the target products. Four of the tested compounds showed inhibition percentages greater than 80%.&lt;/p&gt; &lt;p&gt;&lt;strong&gt;Key words: &lt;/strong&gt;oximes, oxime ethers, isoxazoles, antifungal activity.&lt;/p&gt; &lt;p&gt; &lt;/p&gt;&lt;br /&gt;