[Determination of residual available total and combined free chlorine in water by means of paraaminodimethylaniline].
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Aniline Compounds↗
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Synthesis, antimicrobial activity and molecular modeling studies of halogenated 4-[1H-imidazol-1-yl(phenyl)methyl]-1,5-diphenyl-1H-pyrazoles.
During the course of our studies in the azole antifungals area, we synthesized a number of 1,5-disubstituted 4-[1H-imidazol-1-yl(phenyl)methyl]-1H-pyrazoles, analogues of bifonazole. 1,5-Diphenyl-1H-pyrazole 3 showed weak antimycotic and antibacterial activities in vitro against Candida albicans, Cryptococcus neoformans and Staphylococcus aureus. In order to increase these properties, given that the halo substitution was found to be capable of enhancing antifungal effects, we prepared a series of fluoro and chloro derivatives of 3. The microbiological evaluation carried out on newly synthesized compounds included in vitro assays for antifungal, antibacterial and antimycobacterial activities. Among the tested compounds, some dichloro and trichloro-derivatives showed interesting antimicrobial properties. In particular, compounds 10j,k,l produced inhibitory effects against pathogen representatives of yeast (C. albicans, C. neoformans) and Gram positive bacteria (S. aureus) similar or superior to those of bifonazole. In addition, their activity against Mycobacterium tuberculosis was superior to that of clotrimazole and econazole, which were used as reference drugs. The replacement, in these compounds, of chlorine with fluorine atoms led to inactive derivatives. Docking studies were carried out on the most active compounds, in order to rationalize the pharmacological results.
Anti-Bacterial Agents↗
Toxicologic, pathologic, and immunotoxic effects of 2,4-dichlorophenol in rats.
2,4-Dichlorophenol (DCP) is a drinking and waste-water contaminant formed by the spontaneous reaction of chlorine with phenols following chlorination of water for disinfection and deodorization. Rats were exposed to 0, 3, 30, or 300 ppm DCP in drinking water either in utero or for 12 wk postnatally following in utero exposure. Toxicity to DCP was assessed by organ and body weight changes, histopathology, and effects on reproduction and immunocompetence. Reproductive parameters measured included conception, litter size, pup birth weight, number stillborn, survival to weaning, and weaning weight. Immune parameters assessed were humoral immunity (antibody production) by an indirect enzyme-linked immunosorbent assay (ELISA), cell-mediated immunity by a delayed-type hypersensitivity response, and macrophage function by phagocytosis of radiolabeled blood cells. Rats that received the combined in utero and postnatal treatment with 300 ppm DCP had significantly increased liver and spleen weights, enhanced humoral immune responsiveness, and depressed cell-mediated immunity. Histopathologic changes were unremarkable in DCP-exposed rats, even in the presence of increased liver and spleen weights. The 6-wk-old progeny of DCP-treated dams had normal immune functions and showed no signs of DCP toxicity, other than increased spleen weights in the 300-ppm exposure group. The results indicate that (1) the immune system may be a sensitive target for chlorinated phenolic compounds, (2) DCP may exert different effects on separate major immune responses, and (3) unlike some other chlorinated phenols, DCP does not appear to alter reproductive performance in rats.
Animals↗
Some problems in the detection of strong mutagen MX formed by chlorinating the aromatic acids and phenolic compounds.
Ten compounds with aromatic acid and phenolic structure were chlorinated at laboratory conditions and MX analysis by GC/MS at scan mode. None of these compounds produced MX, which is contrary to the results of other researchers. The whole procedure was investigated and it was found that the results obtained at scan mode was more reliable than at SIM mode because of the possible interference. The structural characteristic of the precursors of MX is proposed.
Amino Acids, Aromatic↗
Relationship between chlorine consumption and chlorination by-products formation for model compounds.
The objective of this research is to investigate the relationship between chlorine decay and the formations of disinfection by-products (DBP), including trichloromethane (TCM) and chloroacetic acid (CAA) in the presence of four model compounds, i.e., resorcinol, phloroglucinol, p-hydroxybenzoic acid, and m-hydroxybenzoic acid. The chlorine degradation in model compounds with OH and/or COOH functional groups were rapid after chlorination. The TCM yields of carboxylic group substituted compounds (3-hydroxybenzoic acid [3-HBA], 4-hydroxybenzoic acid [4-HBA]) were found to be lower than that of the m-dihydroxy substituted compounds. Phloroglucinol, with one more OH substitution group than resorcinol, tends to form significant amounts of CAA after chlorination. However, it was observed that with the COOH substitution of 3-HBA and 4-HBA tend to exhibit more CAA formation potential than resorcinol. The developed parallel second and first-order reaction model for chlorine demand has been successfully utilized for TCM, CAA and DBP formation modeling. A high correlation between CAA and TCM was observed for the model compounds.
Acetates↗
Determination of chlorinated acid herbicides and related compounds in water by capillary electrophoresis-electrospray negative ion mass spectrometry.
Capillary electrophoresis electrospray negative ion mass spectrometry was investigated for the determination of chlorinated acid herbicides and several phenols in water. Sixteen analytes were separated as their anions in less than 40 min with a buffer consisting of 5 mM ammonium acetate in isopropanol-water (40:60, v/v) at pH 10. A sample stacking technique was used to provide lower detection limits and a fortified drinking water sample was made pH 10 and analyzed without further processing. Quantitative analyses with an internal standard gave recoveries in the 91-124% range and replicate measurements of a calibration standard gave relative standard deviations in the range of 3-10%.
Electrophoresis, Capillary↗
Chlorination of bisphenol A: kinetics and by-products formation.
The kinetics of initial chlorination of bisphenol A (BPA) was studied between pH 2 and 11 at room temperature (20 +/- 2 degrees C). pH Profile of the apparent second-order rate constant of the reaction of BPA with chlorine were modeled considering the elementary reactions of HOCl with BPA species and an acid-catalyzed reaction. The predominant reactions at near neutral pH were the reactions of HOCl with the two phenolate species of BPA (k = 3.10 x 10(4) M(-1)s(-1) for BPA- and 6.62 x 10(4) M(-1) s(-1) for BPA(2-)). At near neutral pH, half-life times of BPA were calculated to be less than 1.5 h for chlorine residual higher than 0.2 mg l(-1). Chlorination of synthetic treated waters spiked with BPA showed that BPA disappeared within 4 h and that chlorinated bisphenol A congeners were rapidly formed and remained in solution for up to 10-20 h when low chlorine dosages are applied (0.5-1 mg l(-1)). To limit their presence in drinking water networks, it is then necessary to maintain high chlorine residuals that rapidly produce and decompose chlorinated bisphenol A congeners.
Benzhydryl Compounds↗
Oxidation of bisphenol A, 17beta-estradiol, and 17alpha-ethynyl estradiol and byproduct estrogenicity.
A human breast cancer cell line (MCF-7) was used to investigate the cumulative estrogenicity profiles elicited during the oxidation of three estrogenic compounds [bisphenol A (BPA), 17beta-estradiol (E2), and 17alpha-ethynyl estradiol (EE2)]. High-performance liquid chromatography (HPLC) with a method detection limit (MDL) of approximately 1 nM was used to measure the initial and final concentrations of test compounds during oxidation. Both chlorination and ozonation removed from 75% to >99% of the test compounds in distilled water. Increasing contact time and chlorination dose improved compound removal. Chlorination byproducts of BPA, E2, and EE2 elicited low levels of estrogenicity over an extended period of time. For equivalent molar oxidant dosages, ozone and chlorine had comparable residual proliferative effect values and >99% loss of the parent compounds. For oxidation studies of estrogenic chemicals, ammonium chloride was found to adequately quench residual chlorine without interfering with cell culture assay. Oxidation of test compounds with chlorine and ozone resulted in a similar estrogenicity trend, with a relative higher level of estrogenicity elicited during the early phases of oxidation, which gradually dissipated over the extended exposure time to a stable point. Oxidation with ozone resulted in the rapid transformation of test compounds, reaching a stabilized estrogenic level in 10 min, whereas for chlorination it took more than 120 min for elicited estrogenicity to stabilize.
Benzhydryl Compounds↗
The toxicity of substituted phenols in the nitrification inhibition test and luminescent bacteria test.
The nitrification inhibition test and the luminescent bacteria test were used to determine the inhibiting effect of different phenolic compounds. The chlorinated phenols demonstrated an increased toxicity in the nitrification inhibition test, which was much more sensitive to these compounds than other bacterial toxicity tests. In practice, the nitrification inhibition test was very useful for estimating the toxicity of chemical compounds to nitrifying bacteria, but the test is not recommended for the assessment of general bacterial toxicity. In comparison to other bacterial toxicity tests, the luminescent bacteria test also proved to be very sensitive. Due to its character, which measures a certain physiological parameter, this test system could be used as a screening tool for possible inhibitory effects to bacteria, although positive results should be confirmed by other bacterial toxicity tests.
Ammonium Sulfate↗
The action of 2-anilinothiophenes as accelerators of the deactivation reactions in the watersplitting enzyme system of photosynthesis.
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Aniline Compounds↗
Dioxins: model chemicals for assessing receptor-mediated toxicity.
Dioxins and related compounds are chlorinated aromatic hydrocarbons that are persistent in both environmental and biological samples. Many members of this class of compounds produce a similar spectrum of toxicity which is mediated by interaction with the Ah receptor. The toxic effects of these chemicals can best be described by their actions as growth dysregulators. Dioxins disrupt normal homeostatic processes that tightly regulate cellular growth and differentiation. Disruption in these processes produce a variety of toxicities and pathologies. The available data indicate that humans are sensitive to the toxic effects of these chemicals. Clearer definition of human responses and the body burdens associated with such effects requires more research. Comprehensive risk assessments of dioxins should include all Ah receptor ligands such as the halogenated dibenzofurans and biphenyls.
Animals↗
Long-term performance of permeable reactive barriers using zero-valent iron: geochemical and microbiological effects.
Geochemical and microbiological factors that control long-term performance of subsurface permeable reactive barriers were evaluated at the Elizabeth City, North Carolina, and the Denver Federal Center, Colorado, sites. These ground water treatment systems use zero-valent iron filings (Peerless Metal Powders Inc.) to intercept and remediate chlorinated hydrocarbon compounds at the Denver Federal Center (funnel-and-gate system) and overlapping plumes of hexavalent chromium and chlorinated hydrocarbons at Elizabeth City (continuous wall system). Zero-valent iron at both sites is a long-term sink for carbon, sulfur, calcium, silicon, nitrogen, and magnesium. After about four years of operation, the average rates of inorganic carbon (IC) and sulfur (S) accumulation are 0.09 and 0.02 kg/m2/year, respectively, at Elizabeth City where upgradient waters contain <400 mg/L of total dissolved solids (TDS). At the Denver Federal Center site, upgradient ground water contains 1000 to 1200 mg/L TDS and rates of IC and S accumulation are as high as 2.16 and 0.80 kg/m2/year, respectively. At both sites, consistent patterns of spatially variable mineral precipitation and microbial activity are observed. Mineral precipitates and microbial biomass accumulate the fastest near the upgradient aquifer-Fe0 interface. Maximum net reductions in porosity due to the accumulation of sulfur and inorganic carbon precipitates range from 0.032 at Elizabeth City to 0.062 at the Denver Federal Center (gate 2) after about four years. Although pore space has been lost due the accumulation of authigenic components, neither site shows evidence of pervasive pore clogging after four years of operation.
Environmental Pollution↗
[COMPARISON OF THE BACTERICIDAL ACTION OF CHLORINE AND CHLORINE DIOXIDE].
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Anti-Bacterial Agents↗
Sydnone derivatives. Part VII: Synthesis of some novel thiazoles and their pharmacological properties.
The synthesis of some 4-(arylsydnonyl)-2-(4-arylhydrazono-3-methyl-5-oxo-2-pyrazolin-1-yl)- thiazoles by reacting 1-thiocarboxamido-3-methyl-4-(aryihydrazono)-2-pyrazolin-5-ones with different 4-bromoacetyl-3-arylsydnones is described. A few compounds from this series were screened for their anti-inflammatory, analgesic, and CNS depressant activities. Among the tested compounds 6s, 6d, 6n, and 6u showed significant anti-inflammatory activity comparable with that of standard drug Ibuprofen. Compounds containing chlorine and carboxylic substituents are more active. 6f, 6r, and 6u showed marked analgesic activity and most of the compounds tested showed promising CNS depressant activity comparable with that of standard drug pentobarbitone.
Analgesia↗
Separation of technical 4-nonylphenols and their biodegradation products by comprehensive two-dimensional gas chromatography coupled to time-of-flight mass spectrometry.
Comprehensive two-dimensional gas chromatography (GC x GC) coupled to time-of-flight mass spectrometry (TOF-MS) was applied to improve the separation of 4-nonylphenol isomers and their biodegradation products. The structurally similar nonylphenol isomers were separated by combining a 30 m long semi-polar column and a short polar capillary. Both were coupled via a custom-made liquid nitrogen cryogenic modulator. The advanced GC resolution of coeluting isomers, additionally supported by fast scanning TOF-MS, provided clearer, non-interfered mass spectra of individual isomers. Thus, identification of components is facilitated as shown for isomeric 4-nonylphenols and metabolites of their biodegradation by Clavariopsis aquatica, an aquatic fungus. GC x GC-TOF-MS analysis enabled the separation of about 40 alkylphenol isomers included in technical 4-nonylphenol. During biodegradation the variety of emerging compounds increased with longer reaction time. The comprehensive analysis indicated a broad spectrum of hydroxylated, carboxylated nonylphenolisomers and additionally, chlorinated aromatic compounds produced and released from the fungal culture.
Biodegradation, Environmental↗
Polychlorinated biphenyls and other organic chemical residues in fish from major United States watersheds near the Great Lakes, 1978.
Twenty-six composite samples of fish were collected during 1978 from United States watersheds near the Great Lakes and analyzed for polychlorinated biphenyls (PCBs) and related organic chemicals. PCB mixtures resembling Aroclor 1254 were found in all samples, and mixtures resembling Aroclor 1242 (or 1016) were found in 77 percent of the samples. Total PCB concentrations in the whole-fish composite samples ranged from 0.13 to 14.6 ppm; 65 percent of the samples contained more than 2 ppm PCBs. DDT and its metabolites were found in all samples. sigma DDT concentration was 1.66 ppm, and 81 percent of the samples contained less than 1.0 ppm sigma DDT. Chlordane ranged from less than 0.001 to 2.57 ppm in 38 percent of the samples. Hexachlorobenzene was found in 65 percent of the samples, ranging from less than 0.005 to 0.447 ppm. Other chemicals identified by gas chromatography/mass spectrometry included petroleum hydrocarbons and chlorobenzenes, chlorostyrenes, chlorophenols, and chlorinated aliphatic compounds. Fish from the Ashtabula River (Ohio), Rock River (Ohio), and Wabash River (Indiana) contained extremely complex residues of chlorinated and other organic chemicals.
Animals↗
Guest dechlorination and covalent capture following photoexcitation of inclusion complexes in water.
Photoexcitation of complexes between cyclophane 1 and 1- or 2-chloronaphthalene in aqueous solution leads to rapid dechlorination of the guest, a reaction driven by electron transfer from host to excited guest. The main photoproducts contain a naphthyl group covalently attached to the host framework. The results may lead to new approaches for remediating water contaminated with chlorinated aromatic compounds.
Chlorine↗
Polymer-based adsorption medium prepared using a fragment imprinting technique for homologues of chlorinated bisphenol A produced in the environment.
A polymer-based adsorption medium having molecular recognition ability for homologues of chlorinated bisphenol A produced in environment was prepared using a fragment imprinting technique. 2,6-Dimethyl phenol was utilized as a pseudo-template molecule and the adsorption media prepared was evaluated by high performance liquid chromatography (HPLC) and solid-phase extraction (SPE). As results, the adsorption medium showed preferable chromatographic retention and specific adsorption ability for the chlorinated bisphenol As having chlorine substituents at 3,5-positions through fragment imprinting effect.
Adsorption↗