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PubMed2007

Thermodynamical and quantum-chemical characterization and chemometrical selection of representative congeners of trans-chloroazoxybenzene.

Polychlorinated trans-azoxybenzenes (PCt-AOBs) consist a group of 399 theoretically possible congeners, which are toxicologically and environmentally relevant compounds. Some of PCt-AOBs have been identified as by-side impurity in technical grade 3,4-dichloroaniline (3,4-DCA), and also in derived of this chemical pesticides such as Diuron, Linuron or Propanil. In this study 31 quantum-chemical descriptors were in silico generated and used to characterize all 399 PCt-AOBs. Further, the basic thermodynamic and quantum-chemical property data matrix of PCt-AOBs made was interpreted with an aid of the Principal Component Analysis (PCA). The PCA of these data matrix created a three-dimensional model that explained 77.31% (63.79% + 8.87% + 4.65%) of the total variance. Polarizability, molecular weight, logarithm of the n-octanol/water partition coefficient, molecular refraction, valence molecular index, kappa index, molecular connectivity index, thermal capacity and entropy were the best positively correlated descriptors, which all are connected with molecular shape and size of the molecules. They all are explained by the first principal component (PC1), while energy of the highest occupied molecular orbital, Gibbs free energy in gas phase, standard heat of formation, the total particle energy and thermal energy were negatively correlated. The PC2 depended on polarizability vector Z and energy of the lowest unoccupied molecular orbital, while the PC3 was negatively impacted by the most positive partial charge on atoms. The congeners of trans-PCAOBs substituted with chlorine at positions 2' (ortho position) are non-planar. 119 Congeners of trans-chloroazoxybenzene (Ct-AOB) could be classified amongst stereoisomers (analogues) to highly toxic and environmentally persistent 2,3,7,8-tetrachlorodibenzo-p-dioxin (2,3,7,8-TCDD). Data obtained after PCA were further used to create Fractional Factorial Design of PCt-AOBs and eight congeners, i.e., 2',3'-DiCt-AOB (no. 11), 2,2',5-TrCt-AOB (no. 32), 3',4'-DiCt-AOB (no. 24), 2,4,5-TrCt-AOB (no. 58), 2,2',3,4',5,5'-HeCt-AOB (no. 271), 2,2',3',4',5,5',6'-HpCt-AOB (no. 360), 2,3,3',4,4',5',6-HpCt-AOB (no. 364) and 2,2',3,3',4',5',6'-HpCt-AOB (no. 337), which probably are the best describers of the whole group, could be assigned.

Chlorobenzenes↗
PubMed1984

On the application of cultured neuroblastoma cells in chemical toxicity screening.

The acute toxic action of a number of common chemicals was tested by their ability to cause detachment of cultured mouse neuroblastoma C1300 cells. A TD25 value was obtained by graphic estimation of the concentration needed to cause 25% of the total cell number to detach. These TD25 values were compared with LD50 values obtained from the literature, and they were found to correlate with a coefficient of 0.86. For six of the tested substances-diuron, butylated hydroxytoluene, benzidine, cyclophosphamide, Na2SeO3, and KCN-a very poor correlation was obtained. These diverging results could be ascribed to deficiencies in the neuroblastoma cell detachment test and emphasize the necessity for combined in vitro test procedures.

Animals↗
PubMed1997

A sampling and analytical method for the simultaneous determination of multiple organonitrogen pesticides in air.

An air sampling and analytical method was developed for organonitrogen pesticides using a combined filter and XAD-2 sorbent sampler and high performance liquid chromatography-ultraviolet detection. The method was evaluated for 14 organonitrogen pesticides by National Institute for Occupational Safety and Health evaluation guidelines and procedures. Evaluation experiments addressed limits of detection and quantitation, analytical recovery, sampler capacity, sample stability, and precision and bias over a range of 12 to 240 micrograms per sample. Samples were stable when stored for up to 30 days under either ambient or refrigerated conditions. Based on the finding of this work, 10 of the 14 compounds studied (aldicarb, captan, carbaryl, carbofuran, chlorpropham, diuron, formetanate, methiocarb, oxamyl, propham) can be successfully determined simultaneously using one method with an accuracy of better than +/- 25% of the true value with 95% confidence. Two other compounds (carbendazim/benomyl, methomyl) can be measured with the same accuracy over a more limited concentration range. The remaining two compounds (propoxur, thiobencarb) may meet this criterion, but additional samples would need to be included in the data analysis. With the current data, these two compounds can be determined with an accuracy of better than +/- 27% of the true value with 95% confidence.

Agricultural Workers' Diseases↗
PubMed2003

Multiresidue screening methods for the determination of pesticides in tomatoes.

The possibility of applying thin layer chromatography (TLC) detection for the analysis of pesticide residues in tomatoes was investigated. Samples of tomatoes that have never been treated with pesticide were fortified with atrazine, carbaryl, carbofuran, chloroxuron, diuron, dimethoate, imazalil, oxamyl and methamidophos. The samples were extracted, cleaned-up by gel permeation chromatography and then applied on silica gel plates. The pesticides were eluted with ethyl acetate and dichloromethane. Two eluting solvent systems were tested, one using the reagents o-toluidine + potassium iodite (o-TKI) and the other p- nitrobenzene fluoroborate (NBFB). After the development of the plates, the diameter of the spots was measured. The lowest minimum detection quantity (MDQ) for o-TKI system for atrazine was 12 ng. The highest was 125 ng for carbofuran. Using NBFB system, the lowest MDQ was 60 ng for carbaryl and the highest was 70 ng obtained for carbofuran. Considering the concentration of these pesticides in the spiked tomato samples, the minimum concentration was 1.1 ng/microL and 32.3 ng/microL for atrazine and carbofuran, respectively, by using o-TKI system. For NBFB system the minimum concentration reached was 3.5 ng/microL and 4.3 ng/microL for carbaryl and carbofuran, respectively. This study showed that TLC can be used for semi-quantitative analysis.

Calibration↗
PubMed2005

Application of an artificial sea salt solution to determine acute toxicity of herbicides to Proisotoma minuta (Collembola).

The acute toxicity test is described in this experiment where the Collembola species Proisotoma minuta was exposed to herbicides in an artificial sea salt solution for seven days. The salt solution did not prohibit the insects' reproduction system. The seven day LD50 values for trifluralin, pendimethalin, metolachlor, prometryn, paraquat, atrazine, fluometuron, and diuron were 3.48, 10.4, 12.4, 13.0, 23.1, 33.4, 250, and 711 mg L(-1), respectively. A good correlation between toxicity of the compounds and their lipophilicity and vapor pressure was recorded in this study.

Animals↗
PubMed1990

Biomonitoring of arylamines: hemoglobin adducts of urea and carbamate pesticides.

Hemoglobin adducts of aromatic amines released from pesticides were investigated. Female Wistar rats were dosed orally with pesticides up to 1 mmol/kg body weight. Blood was obtained after 24 h, hemoglobin isolated and hydrolyzed in 1 NaOH. The amines were extracted and quantified by gas chromatography with nitrogen-specific or mass-selective detection. The following binding indices [HBI, hemoglobin binding index = binding (mmol/mol Hb) per dose (mmol/kg)] were obtained: pesticide (arylamine): linuron, diuron (3,4-dichloroaniline) 0.8 and 4.5 respectively; monuron, monolinuron (4-chloroaniline) 39 and 55 respectively; chlorpropham (3-chloroaniline) 2.9; chlordimeform (4-chloro-o-toluidine) 2.4; propham (aniline) 2.4. With vinclozoline and iprodione (3,5-dichloroaniline) and quintozene (pentachloroaniline) no adducts could be found. The results demonstrate the possible use of arylamine-hemoglobin adducts for measuring the bioavailability of potentially hazardous components of pesticides and the extent to which they are formed and metabolically activated.

Animals↗
PubMed1999

High-performance liquid chromatography column switching applied to the trace determination of herbicides in environmental and drinking water samples.

A selective and sensitive coupled-column high-performance liquid chromatographic method is developed for the simultaneous determination of 5 phenylurea herbicides (monuron, linuron, isoproturon, monolinuron, and diuron) in environmental and drinking water samples. Sample clean-up is performed automatically by means of a column switching technique. Using 2 octadecyl silica columns connected via two programmable 6-port valves and ultraviolet detection at 244 nm, the aforementioned compounds can be determined at the low concentration levels required for pesticide residue analysis in water samples. A mobile phase consisting of a mixture of methanol-water (55:45, v/v) is pumped at 1 mL/min. For the 5 phenylureas, high recoveries ranging from 94.9 to 101.6%, good reproducibility with relative standard deviations lower than 5%, and wide linear ranges up to 20 micrograms/L are observed with determination limits of 0.05 microgram/L. The method is successfully applied to the screening of different environmental water samples such as surface, ground, rain, and drinking water.

Chromatography, High Pressure Liquid↗
PubMed2002

Toxicity of single and mixed contaminants in seawater measured with acute toxicity bioassays.

Different types of organic pollutants commonly detected in seawater have been evaluated by acute toxicity bioassays. Vibrio fischeri, Daphnia magna, and Selenastrum capricornotum were selected to test toxic effects of individual compounds and mixtures of these compounds, obtaining EC50 values in the range of 0.001 to 28.9 mg/l. In the case of mixtures, synergistic toxic responses were seen for a clear majority of the cases (>60%). Mixtures containing methyl-tertiary-butyl ether (MTBE) exhibit accelerated processes that result in a change in concentration required to produce a toxic effect; for example, in the case of mixtures containing MTBE and Diuron and Dichlofluanid.

Animals↗
PubMed2003

The sulfolipids 2'-O-acyl-sulfoquinovosyldiacylglycerol and sulfoquinovosyldiacylglycerol are absent from a Chlamydomonas reinhardtii mutant deleted in SQD1.

The biosynthesis of thylakoid lipids in eukaryotic photosynthetic organisms often involves enzymes in the endoplasmic reticulum (ER) and the chloroplast envelopes. Two pathways of thylakoid lipid biosynthesis, the ER and the plastid pathways, are present in parallel in many species, including Arabidopsis, but in other plants, e.g. grasses, only the ER pathway is active. The unicellular alga Chlamydomonas reinhardtii diverges from plants like Arabidopsis in a different way because its membranes do not contain phosphatidylcholine, and most thylakoid lipids are derived from the plastid pathway. Here, we describe an acylated derivative of sulfolipid, 2'-O-acyl-sulfoquinovosyldiacylglycerol (ASQD), which is present in C. reinhardtii. Although the fatty acids of sulfoquinovosyldiacylglycerol (SQDG) were mostly saturated, ASQD molecular species carried predominantly unsaturated fatty acids. Moreover, directly attached to the head group of ASQD was preferentially an 18-carbon fatty acid with four double bonds. High-throughput robotic screening led to the isolation of a plasmid disruption mutant of C. reinhardtii, designated Deltasqd1, which lacks ASQD as well as SQDG. In this mutant, the SQD1 ortholog was completely deleted and replaced by plasmid sequences. It is proposed that ASQD arises from the sugar nucleotide pathway of sulfolipid biosynthesis by acylation of the 2'-hydroxyl of the sulfoquinovosyl head group. At the physiological level, the mutant showed increased sensitivity to a diuron herbicide and reduced growth under phosphate limitation, suggesting a role for SQDG and/or ASQD in photosynthesis as conducted by C. reinhardtii, particularly under phosphate-limited conditions.

Acylation↗
PubMed1997

Thermostability and Photostability of Photosystem II in Leaves of the Chlorina-f2 Barley Mutant Deficient in Light-Harvesting Chlorophyll a/b Protein Complexes.

The chlorophyll-b-less chlorina-f2 barley mutant is deficient in the major as well as some minor light-harvesting chlorophyll-protein complexes of photosystem II (LHCII). Although the LHCII deficiency had relatively minor repercussions on the leaf photosynthetic performances, the responses of photosystem II (PSII) to elevated temperatures and to bright light were markedly modified. The chlorina-f2 mutation noticeably reduced the thermostability of PSII, with thermal denaturation of PSII starting at about 35[deg]C and 38.5[deg]C in chlorina-f2 and in the wild type, respectively. The increased susceptibility of PSII to heat stress in chlorina-f2 leaves was due to the weakness of its electron donor side, with moderate heat stress causing detachment of the 33-kD extrinsic PSII protein from the oxygen-evolving complex. Prolonged dark adaptation of chlorina-f2 leaves was also observed to inhibit the PSII donor side. However, weak illumination slowly reversed the dark-induced inhibition of PSII in chlorina-f2 and cancelled the difference in PSII thermostability observed between chlorina-f2 and wild-type leaves. The mutant was more sensitive to photoinhibition than the wild type, with strong light stress impairing the PSII donor side in chlorina-f2 but not in the wild type. This difference was not observed in anaerobiosis or in the presence of 3-(3,4-dichlorophenyl)- 1,1-dimethylurea, diuron. The acceptor side of PSII was only slightly affected by the mutation and/or the aforementioned stress conditions. Taken together, our results indicate that LHCII stabilize the PSII complexes and maintain the water-oxidizing system in a functional state under varying environmental conditions.

Journal Article↗
PubMed1980

Evidence for HCO(3) Transport by the Blue-Green Alga (Cyanobacterium) Coccochloris peniocystis.

The possibility of HCO(3) (-) transport in the blue-green alga (cyanobacterium) Coccochloris peniocystis has been investigated. Coccochloris photosynthesized most rapidly in the pH range 8 to 10, where most of the inorganic C exists as HCO(3) (-). If photosynthesis used only CO(2) from the external solution the rate of photosynthesis would be limited by the rate of HCO(3) (-) dehydration to CO(2). Observed rates of photosynthesis at alkaline pH were as much as 48-fold higher than could be supported by spontaneous dehydration of HCO(3) (-) in the external solution. Assays for extracellular carbonic anhydrase were negative. The evidence strongly suggests that HCO(3) (-) was a direct C source for photosynthesis.Weakly buffered solutions became alkaline during photosynthesis with a one-to-one stoichiometry between OH(-) appearance in the medium and HCO(3) (-) initially added. Alkalization occurred only during photosynthesis and was blocked by 3-(3,4-dichlorophenyl)-1, 1-dimethylurea, diuron. It is suggested that HCO(3) (-) was transported into cells of Coccochloris in exchange for OH(-) produced as a result of HCO(3) (-) fixation in photosynthesis.The inorganic C concentration required to support a rate of photosynthesis of half the maximum rate (K(m)) was 6 micromolar at pH 8.0 or, in terms of available CO(2), a K(m) of 0.16 micromolar. This value is two orders of magnitude lower than reported K(m) values for the d-ribulose-1,5-bisphosphate carboxylase for blue-green algae. It is suggested that the putative HCO(3) (-) transport by Coccochloris serves to raise the CO(2) concentration around the carboxylase to levels high enough for effective fixation.

Journal Article↗
PubMed1981

In Vivo Nitrite Reduction in Leaf Tissue of Phaseolus vulgaris L.

Experiments were performed to establish a procedure for in vivo measurement of nitrite utilization by leaf tissue of bean (Phaseolus vulgaris L. cv. Top Crop).To measure light-dependent nitrite disappearance, a single disc of leaf tissue was exposed to light for 1 hour at 30 C while immersed in incubation medium (approximately 0.11 milliliter per square centimeter of leaf area) in the bottom of a tall-form glass beaker. The incubation medium was 100 millimolar phosphate buffer (pH 7.5) with added wetting agent and nitrite. The wetting agent combination of 1% 1-propanol plus 0.05% Neutronyx-600 was used in some experiments for compatibility with established in vivo nitrate reductase (NR) assays; however, 0.05% Neutronyx-600 alone was found to be a suitable substitute. Parallel assays run in the dark on related tissue are recommended as a means to determine the amount of nitrite synthesized within the tissue by the NR system. Adding the results of the two assays gives an estimate of total nitrite utilization by the leaf tissue. It was found that 20 millimolar nitrite in the incubation medium was the most suitable level of external nitrite for promoting light-dependent nitrite disappearance. This was also found to reduce, sometimes to zero, the rate of synthesis of nitrite by NR. NR activity declined steadily with advancing age. Except for very young tissue, the rate of nitrite disappearance was independent of age. Nitrite disappearance was completely blocked by diuron.

Journal Article↗
PubMed1981

The Azolla-Anabaena azollae Relationship : XI. PHYCOBILIPROTEINS IN THE ACTION SPECTRUM FOR NITROGENASE-CATALYZED ACETYLENE REDUCTION.

Visible absorption spectra are presented for the Azolla caroliniana Willd.-Anabaena azollae Strass. association and the individual partners. Although absorption by the phycobiliproteins of the endophytic cyanobacterium clearly complements the absorption by the fern pigments, their contribution to the absorption spectrum of the association is effectively concealed by the preponderance of the Azolla pigments. Action spectra for nitrogenase-catalyzed C(2)H(2) reduction in both the Azolla-Anabaena association and the endophytic Anabaena demonstrate that quanta absorbed by the phycobiliproteins is as effective as that absorbed by chlorophyll a in driving this photosystem I-linked process. Under anaerobic conditions, the inhibition of photosystem II activity by 3-(3,4-dichlorophenyl)-1,1-dimethylurea, diuron did not selectively decrease the relative quantum yields in the region of phycobiliprotein absorption. At the well-below saturating light intensities used for the action spectra studies, the absolute rates of C(2)H(2) reduction were increased uniformly via respiratory-linked processes under aerobic conditions. The occurrence of phycobiliproteins in heterocysts of the endophytic Anabaena was demonstrated using fluorescence microscopy of intact filaments. Fluorescence micrographs of Anabaena cylindrica filaments are presented for comparison.

Journal Article↗
PubMed1982

Photosystem II Activity, Plastoquinone A Levels, and Fluorescence Characterization of a Virescens Mutant of Barley.

Chloroplasts isolated from seedlings of a virescens mutant of barley (Hordeum vulgare L cv Gateway) grown for 6 days under continuous illumination had lower levels of photosystem II activities on a chlorophyll basis than wild-type seedlings. After 8 days, however, the photosystem II rates of the mutant and wild-type were approximately equal. Lower levels of the photosystem II activities in the mutant were correlated with a smaller functional plastoquinone pool size as determined by room temperature fluorescence induction. Higher levels of extractable plastoquinone A on a chlorophyll basis, however, were obtained from mutant chloroplasts. An increased room temperature fluorescence yield in the mutant was shown to be due to a higher level of initial fluorescence. A decreased sigmoidicity in the room temperature fluorescence induction transient in the presence of diuron and an increased 77 K fluorescence emission at 680 nanometers lead us to believe that a certain population of the light harvesting chlorophyll protein complex in the mutant membranes is unconnected to photo-system II reaction centers. Although photochemical activities of the mutant approach wild-type values as the mutant develops, the population of dissociated light harvesting complexes does not appear to change.

Journal Article↗
PubMed1983

Relation between Respiration and Senescence in Oat Leaves.

The respiration of excised oat (Avena sativa cv Victory) leaves and their sensitivity to inhibitors was followed during senescence under varied conditions. The respiration rate, which in controls reaches its peak on the third day in darkness, is lowered at the time of fastest loss of chlorophyll (as reported earlier) by seven unrelated reagents that all delay dark senescence. When senescence is delayed by white light or by cytokinins, the respiratory rise is correspondingly delayed. Kinetin and l-serine, which act as antagonists on senescence, also act as antagonists on the respiratory rate. However, an exception to this close correspondence between senescence and the respiratory rise is offered by the lower aliphatic alcohols, which delay dark senescence and yet accelerate the onset of the respiratory rise.The respiration of freshly cut leaves is insensitive to KCN up to 8 millimolar, but sensitive to benzhydroxamate (BAM), 1 to 2 millimolar BAM causing 25% promotion and higher concentrations inhibiting. At the respiratory peak, however, part of the respiration becomes KCN-sensitive. Low concentrations of alcohols in darkness, or 3-(3,4-dichlorophenyl)-1,1-dimethylurea, diuron, in light, also render part of the respiration KCN-sensitive, but this sensitivity soon disappears again. Some 10 to 15% of the respiration is insensitive to both inhibitors. Thus, cyanide sensitivity comes and goes, while BAM sensitivity is always present. The current concept of the cyanide-resistant pathway as an overflow, therefore, does not fit well with behavior of these leaves. The respiratory rise in leaf senescence is similar to, but not identical with, the climacteric in ripening fruits and the aging phenomenon in tuber slices.

Journal Article↗
PubMed1984

Photosynthetic electron transport in guard cells of diverse species.

Guard cells of plants representing 18 species were assayed qualitatively for potential to conduct photosynthetic linear electron transport. These plants included C(3) pteridophytes, C(3) and C(4) monocots, and C(3), C(4), and Crassulacean acid metabolism dicots. By use of a microfluorospectrophotometer, guard cell samples in epidermal peels were isolated optically. Chlorophyll fluorescence was monitored from the onset of excitation light. For guard cells of all these species, fluorescence intensity increased during illumination. When samples were preincubated with 3-(3,4-dichlorophenyl)-1,1-dimethylurea, diuron, however, there was a more rapid increase in fluorescence. These results indicate that all tested guard cells conduct photosynthetic electron transport through the reaction center of photosystem II.

Journal Article↗
PubMed1990

Cooperative regulation of cytoplasmic streaming and ca fluxes by pfr and photosynthesis in vallisneria mesophyll cells.

In mesophyll cells of Vallisneria gigantea Graebner, Ca(2+) regulates the induction and cessation of cytoplasmic streaming. Streaming is induced when the level of calcium in the cytoplasm is lowered through light-accelerated release of Ca(2+) from the cells (S Takagi, R Nagai [1988] Plant Physiol 88: 228-232). We have now initiated an investigation on the nature of the photoreceptor(s) that are involved in the regulation of Ca(2+) movements across the cell membrane and of streaming. Streaming is induced only when phytochrome exists in the phytochrome-far redabsorbing form (Pfr)-and photosynthesis is allowed to take place for at least 4 minutes. The former effect is typically photoreversible by red and far-red light, and phytochrome is spectro-photometrically detectable in the crude extract from the leaves. The latter effect is assessed in terms of the wavelength dependency and the effects of diuron and atrazine, two inhibitors of photosynthesis. A similar requirement for Pfr and photosynthesis is found to be associated with the acceleration of Ca(2+) efflux in the protoplasts. The results suggest that phytochrome and photosynthetic pigment(s) cooperatively regulate cytoplasmic streaming via modulation of the Ca(2+) transport in the cell membrane.

Journal Article↗
PubMed1991

In Vivo and In Vitro Protein Phosphorylation Studies on Ochromonas danica, an Alga with a Chlorophyll a/c/Fucoxanthin Binding Protein.

The phosphorylation of thylakoid membranes in the Chromophyte alga Ochromonas danica was studied in whole cells and in vitro. Protein kinase activity was observed in the thylakoid fraction, and several membrane-bound polypeptides were found to be phosphorylated. The thylakoid protein kinase demonstrated several unusual regulatory properties. Both the polypeptides that were phosphorylated and the rate of protein phosphorylation were independent of illumination. Protein kinase activity was also unaffected by 3-(3,4-dichlorophenyl)-1,1-dimethylurea, diuron. The kinase activity was inhibited under strong reducing conditions. Whole cells labeled with (32)PO(4) (3-) were converted to light states I and II by pre-illumination favoring photosystem I or photosystem II, respectively. Analysis of the phosphoproteins from cells in state I and state II showed that no changes in phosphorylation accompanied the change in energy redistribution.

Journal Article↗