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PubMed2003

Cross-resistance to strobilurin fungicides in mitochondrial and nuclear mutants of Saccharomyces cerevisiae.

In yeast the resistance to kresoxim-methyl and azoxystrobin, like the resistance to strobilurin A (mucidin) is under the control of both mitochondrial cob gene and the PDR network of nuclear genes involved in multidrug resistance. The mucidin-resistant mucl (G137R) and muc2 (L275S) mutants of Saccharomyces cerevisiae containing point mutations in mtDNA were found to be cross-resistant to kresoxim-methyl and azoxystrobin. Cross-resistance to all three strobilurin fungicides was also observed in yeast transformants containing gain-of-function mutations in the nuclear PDR3 gene. On the other hand, nuclear mutants containing disrupted chromosomal copies of the PDR1 and PDR3 genes or the PDR5 gene alone were hypersensitive to kresoxim-methyl, azoxystrobin and strobilurin A. The frequencies of spontaneous mutants selected for resistance either to kresoxim-methyl, azoxystrobin or strobilurin A were similar and resulted from mutations both in mitochondrial and nuclear genes. The results indicate that resistance to strobilurin fungicides, differing in chemical structure and specific activity, can be caused by the same molecular mechanism involving changes in the structure of apocytochrome b and/or increased efflux of strobilurins from fungal cells.

ATP-Binding Cassette Transporters↗
PubMed2002

Effects of the dithiocarbamate fungicide propineb in primary neuronal cell cultures and skeletal muscle cells of the rat.

After repeated-dose toxicity studies with the fungicide propineb, reversible effects on muscle functions were found. Therefore, mechanistic investigations should contribute to clarification of its mode of action in relation to disulfiram and diethyldithiocarbamate neurotoxicity or direct effects on muscle cells. In principle, besides the dithiocarbamate effects, two different mechanisms have been discussed for this fungicide. One mechanism is the degradation to carbon disulfide (CS(2)) and propylenthiourea (PTU) and the other are direct effects of zinc. Primary neuronal cell cultures of the rat are a well established model to identify neurotoxic compounds like n-hexane or acrylamide. In this cell culture model, endpoints such as viability, energy supply, glucose consumption and cytoskeleton elements were determined. Additionally, skeletal muscle cells were used for comparison. Propineb and its metabolite PTU were investigated in comparison to CS(2), disulfiram and diethyldithiocarbamate. The toxicity of zinc was tested using zinc chloride (ZnCl(2)). It was clearly shown that propineb exerted strong effects on the cytoskeleton of neuronal and non-neuronal cell cultures (astrocytes, muscle cells). This was similar to ZnCl(2,) but not to CS(2). With CS(2) and disulfiram effects on the energy supply were more prominent. In conclusion, the toxicity of propineb is not comparable to disulfiram, diethyldithiocarbamate or CS(2) neurotoxicity. In regard to these findings, a direct reversible effect of propineb on skeletal muscle cells seems to be more likely.

Animals↗
PubMed2006

Application of matrix solid-phase dispersion and liquid chromatography-mass spectrometry to fungicide residue analysis in fruits and vegetables.

A method based on matrix solid-phase dispersion (MSPD) and liquid chromatography-electrospay ionization-mass spectrometry used to analyze fifteen fungicide residues in fruits and vegetables is described. The method required only 0.5 g of sample, C(18)-bonded silica was used as dispersant sorbent, and ethyl acetate was used as eluting solvent. Fortified recoveries in apple, orange, banana, lettuce, grape and tomato samples ranged from 71% to 102% and relative standard deviations were less than 13% with fortified levels of 0.03-1.5 mg kg(-1). Detection and quantification limits were 1 approximately 30 microg kg(-1) and 4 approximately 100 microg kg(-1), respectively, with linear calibration curves extending up to 15 mg kg(-1). The analytical characteristics of MSPD compared very favorably with those found for a classical multiresidue method: the quick, easy, cheap, effective, rugged, and safe (QuEChERS) method. The method was applied to determine the fungicides in real samples. Liquid chromatography-tandem mass spectrometry (LC-MS-MS) was used as confirmatory tool for positive samples.

Chromatography, Liquid↗
PubMed2006

Induction of morphological deformities and moulting alterations in Litopenaeus vannamei (Boone) juveniles exposed to the triazole-derivative fungicide tilt.

A tropical marine bioassay was developed with juveniles of Pacific white shrimp, Litopenaeus vannamei, in order to test the acute and sublethal toxicity of Tilt, which is the commercial formulation of the fungicide propiconazole. A 10-d acute toxicity and a 32-d sublethal test were performed. A median lethal concentration (LC50) was determined for different exposure times, resulting in a 24-h LC50 of 1167 (1101-1386) microg/L (concentration based on active ingredient propiconazole), and reaching a threshold LC50 (72-h) at 1043 (1018-1068) microg/L. The sublethal exposure test was performed with propiconazole concentrations ranging from 367 to 825 microg/L. Animals in most treatments showed a significant increase in intermoult duration compared to those in the control treatment, although this did not seem to be concentration-dependent. However, the shrimps exposed to the sublethal concentrations of this fungicide showed morphological deformities, with a significant positive relationship between concentration and deformities of the rostrum, paraeopods, and uropods. Altogether, the results presented indicate the potential effects of Tilt on shrimp, particularly under long-term exposures, although these were found to occur at concentrations exceeding those reported in natural environments.

Animals↗
PubMed2000

Hemocytic lysosome response in the snail Helix aspersa after exposure to the fungicide copper oxychloride.

This study investigated the use of lysosomal responses of hemocytes of the common garden snail, Helix aspersa, as biomarker of stress due to exposure to the fungicide copper oxychloride. The neutral red retention (NRR) time assay was employed for this purpose. Two groups of snails were exposed to 80 microg g(-1) and 240 microg g(-1) copper oxychloride in their food, respectively, for a period of 6 weeks. They were compared with a control group to which no copper oxychloride was added. The two groups exposed to the fungicide exhibited significantly higher (p < 0.001) whole body copper concentrations (200.85 +/- 53.5 and 272.24 +/- 67.15 microg g(-1) dry mass, respectively), and significantly shorter (p < 0.001) NRR times (10.22 +/- 3.53 and 2.67 +/- 2.83 min, respectively), after 6 weeks, compared to the control group (67.85 +/- 31.08 microg g(-1) dry mass and 24.44 +/- 8.35 min). In both exposure groups NRR times became progressively shorter as body copper concentrations increased over time. Thus, both exposure concentration and exposure time of copper oxychloride were shown to be important factors influencing lysosomal responses (and therefore NRR times) of H. aspersa hemocytes. It was concluded that these responses in this species, as measured by the NRR time assay, could be considered a useful cellular biomarker of stress resulting from exposure to copper oxychloride.

Animals↗
PubMed2000

Characterization of laboratory mutants of Venturia inaequalis resistant to the strobilurin-related fungicide kresoxim-methyl.

Several agricultural fungicides related to the antifungal strobilurins act as inhibitors of respiration by binding to mitochondrial cytochrome b. Two types of laboratory mutants resisting higher doses of the strobilurin-related inhibitor kresoxim-methyl were characterized for Venturia inaequalis, the causal agent of apple scab. Selection of mutagenized conidia by kresoxim-methyl yielded mutants altered in the expression of alternative respiration during the stage of conidia germination. Cytochrome b sequences were not affected in the respective mutants. Selection of conidia on media containing the alternative oxidase inhibitor salicylhydroxamic acid in addition to kresoxim-methyl yielded a highly resistant mutant distinguished by a G143A exchange in cytochrome b. The status of mitochondrial cytochrome b genes remained heteroplasmic, and mitochondria containing wild-type cytochrome b returned to high frequencies during cultivation on inhibitor-free medium. However, continuation of the selection process led to a more pronounced replacement of sensitive by mutated mitochondria. The G143A mutation of cytochrome b causing resistance of V. inaequalis to a strobilurin-related inhibitor has been reported previously for mouse mitochondria; and a permanent G143A exchange rendering naturally resistant mitochondria has been reported for the strobilurin-producing basidiomycete Mycena galopoda and for the sea urchin Paracentrotus lividus. At the corresponding position, alanine was also present in chloroplast cytochrome b6 exhibiting low binding of strobilurin-related inhibitors. The mutation of cytochrome b reported here for V. inaequalis describes the first example of a mutation in filamentous ascomycetes and is part of an assessment of resistance risks inherent to strobilurin fungicides.

Amino Acid Sequence↗
PubMed1993

Application of solid-phase partition cartridges in the determination of fungicide residues in vegetable samples.

Disposable, ready-to-use cartridges filled with a macroporous diatomaceous material are used to extract in a single step fungicide residues with dichloromethane from aqueous acetone extracts of vegetables. This procedure takes the place of some functions (such as separating funnel partition, drying over anhydrous sodium sulphate and clean-up) usually performed by separate steps in classical schemes. Fourteen fungicides (dichloran, vinclozolin, chlorthalonil, triadimefon, dichlofluanide, procymidone, hexaconazole, captan, folpet, ditalimfos, iprodione, captafol, pyrazophos and fenarimol) were determined using the described procedure with recoveries between 83 and 107% at spiking levels ranging for the different compounds from 0.04 to 0.40 mg/kg. Crops subjected to the described procedure included lettuce, strawberry, apple, yellow pepper and peach, and gave extracts containing a mass of co-extractives between 5 and 30 mg. Compared with classical schemes, the described procedure is simple, less labour intensive, allows parallel handling of several extracts and does not require preparation and maintenance of equipment. Troublesome emulsions such as those frequently observed in separating funnel partitioning do not occur.

Chromatography, Gas↗
PubMed1992

Evidence of reduced poly-B-hydroxybutyrate biosynthesis in free-living nitrogen-fixing bacteria, Azotobacter chroococcum, following acquired resistance to the fungicide captan.

Some biological activities of Azotobacter chroococcum, strain Azcap 1, (spontaneous mutant, captan resistant up to 300 micrograms/ml) were assayed on RM medium with and without the presence of the fungicide. Comparisons were also carried out with Az. chroococcum sensitive strains Azwt, Azcan 10 and 14. The hydrolysis of captan, incorporated in agar plates of RM at 100 micrograms/ml, was rapid, since on 4-day plates, no effect was found on the strain Azwt, while on freshly prepared ones its growth was completely blocked. As for Azcap 1, grown on RM only, the behaviour was similar to that of sensitive strains, whereas when grown on captan the results of experiments showed: (i) a lag of approximately 12 h to reach the maximum nitrogen-fixing activity; (ii) delay of 12-24 h in the full consumption of glucose present in the medium, although the invertase activity did not present differences; (iii) high ATP culture content during the 50 h of the experiment; (iv) approximately 6-10-fold lower production of PHB (poly-B-hydroxybutyrate); (v) lack of typical encystment phase, for the tested 96 h and reduced viability in developing colonies on agar RM medium. In contrast, when captan was added to cultural medium at sublethal concentration, 50 micrograms/ml for sensitive strain Azwt and 200 micrograms/ml for Azcap 1, the amount of glutathione produced (to remove the fungicide toxicity) was several times higher for the former.

Azotobacter↗
PubMed1976

The mutagenic effect of the mercury fungicide Ceresan M in Drosophila melanogaster.

After the 1972 mercury poisoning in Iraq, there was widespread concern over the use of mercury fungicides in seed dressing. The ethyl mercury fungicide Ceresan M, claimed to be responsible for the two earlier outbreaks of poisoning in 1956 and 1960 in Iraq, was tested in Drosophila to study its mutagenic potentialities. Of the two concentrations used, namely 30 and 40 mg of the chemical in 100 cc of the food medium, the latter treatment resulted in a significant increase in the frequency of sex-linked recessive lethals.

Animals↗
PubMed1983

Evaluation of mutagenic effect of the fungicide fenaminosulf in Drosophila melanogaster.

Fenaminosulf (p-dimethylaminobenzenediazo sodium sulfonate, CAS registry No. 140-56-7) which is an active ingredient in several commercial fungicides was reported to be mutagenic in Salmonella typhimurium (McCann et al., 1975), Bacillus subtilis (Kada et al., 1974) and shown to cause chromosome aberrations in plants (Zutshi and Kaul, 1975). Since fenaminosulf has structural similarity to the potent carcinogen, butter yellow (p-dimethylaminoazobenzene, CAS registry No. 60-11-7), the present studies were undertaken to evaluate the mutagenic potential of this fungicide in Drosophila melanogaster. Fenaminosulf administered at 10 mg/100 ml food medium failed to induce sex-linked recessive mutations in Drosophila. Since Drosophila has drug-metabolizing enzymes similar to those of mammals (Vogel, 1975), it is suggested that the lack of mutagenic activity of fenaminosulf could be due to the conversion of fenaminosulf to non-mutagenic derivatives in Drosophila.

Animals↗
PubMed1982

Cytogenetic hazards from agricultural chemicals. 4. Sequential screening in the barley progeny test for cytogenetic activity of some systemic fungicides and a metabolite.

Four systemic fungicides and a metabolite: Benomyl, Carbendazim, Thiophanate-methyl, Dexon and dimethyl phenylenediamine were screened in the barley progeny test for cytogenetic activity. All affected germination, seedling growth, mitotic and meiotic activity, pollen fertility and seedset in the M1 generation to different degrees; however, no chlorophyll mutations were induced and the M1 effect were much reduced in the M2 progeny. Though the results compare well with those from studies on mammalian cells, the use of these fungicides may not affect the plant breeder and the user of grain.

Chromosome Aberrations↗
PubMed1996

A structure-activity relationship for the neurotoxicity of triazole fungicides.

Previous work has demonstrated that acute exposures to the triazole fungicide triadimefon affects central nervous system (CNS) catecholamines and induces a transient syndrome in rats that consists of hyperactivity and stereotyped behaviors. The present research was designed to determine whether this type of CNS toxicity is characteristic of other triazoles. Dose-effect functions were determined for 14 different triazoles or structurally related pesticides in adult male Long-Evans rats. All chemicals were administered per os in corn oil. Hyperactivity was measured for 2 h in figure-eight mazes. Results indicated that only triadimefon and triadimenol were able to induce hyperactivity; none of the other chemicals produced this effect. These data suggest a very rigid structure-activity relationship (SAR) for the hyperactivity syndrome and indicate that CNS effects may be minimized in the future design of triazoles without impacting fungicidal efficacy.

Animals↗
PubMedDate not supplied

Bitertanol, a triazole fungicide, increases operant responding but not motor activity.

Several recent reports indicate that triadimefon, a triazole fungicide, has effects on behavior that are similar to those of psychomotor stimulants. For example, triadimefon increases overall fixed-interval (FI) response rate, disrupts FI response patterning, increases motor activity, and produces stereotypies at high doses. The present study was designed to determine whether similar behavioral effects on FI performance and motor activity could be produced by another triazole fungicide, bitertanol. The effects of bitertanol (10-300 mg/kg, IP) were determined in rats on performance maintained under a multiple FI 1-min FI 5-min schedule of reinforcement. Intermediate doses of bitertanol increased response rates and disrupted response patterning in both FI components. A second experiment determined the effects of the same doses of bitertanol on motor activity. In contrast to its effects on operant responding, bitertanol did not increase motor activity at any of the doses tested. These findings indicate that the behavioral similarities between bitertanol and triadimefon are limited and that a dissociation exists between biteranol's effects on operant performance and motor activity.

Animals↗
PubMed2004

Expression of behavioral sensitization to the cocaine-like fungicide triadimefon is blocked by pretreatment with AMPA, NMDA and DA D1 receptor antagonists.

Triadimefon (TDF) is a triazole fungicide that blocks the reuptake of dopamine (DA), much like cocaine. A recent study in our laboratory found that intermittent injections of TDF led to robust locomotor sensitization in response to challenge TDF after a 2-week withdrawal period. The current study sought to determine whether the expression of TDF behavioral sensitization could be prevented by the DA D1-like receptor antagonist SCH 23390 (SCH), the DA D2-like receptor antagonist remoxipride (Rem), the competitive NMDA antagonist CPP, or the AMPA antagonist NBQX. Adult male C57/BL6 mice were injected with vehicle or 75 mg/kg TDF twice a week for 7 weeks, with locomotor activity measured periodically across the 14 doses. After a 2-week withdrawal period, mice were pretreated with SCH (0.015 mg/kg), Rem (0.3 mg/kg), CPP (2.5 mg/kg) or NBQX (10.0 mg/kg) followed 30 min later by vehicle or 75 mg/kg TDF and tested for the expression of TDF sensitization. Intermittent administration of TDF led to the development and robust expression of behavioral sensitization in terms of vertical activity. Pretreatment with SCH, NBQX and CPP successfully blocked the expression of vertical sensitization to TDF, while Rem pretreatment did not. All four antagonists, however, attenuated the neurochemical changes normally associated with TDF sensitization as measured 8 h after the 2-week TDF challenge. This paper reveals that NMDA, AMPA and DA D1-like receptors are necessary for the behavioral expression of sensitization to the fungicide triadimefon.

Animals↗
PubMed2004

High temperature liquid chromatography of triazole fungicides on polybutadiene-coated zirconia stationary phase.

High temperature liquid chromatography using water-rich and superheated water eluent is evaluated as a new approach for the separation of selected triazole fungicides, hexaconazole, tebuconazole, propiconazole, and difenoconazole. Using a polybutadiene-coated zirconia column at temperatures of 100-150 degrees C, clear separations were achieved when 100% purified water was utilized as organic-free eluent. Excellent limits of detection down to pg level were obtained for the separation of the triazole fungicides under optimum conditions. Van't Hoff plots for the separations were linear suggesting that no changes occurred in the retention mechanism over the temperature range studied.

Butadienes↗
PubMed2005

Discovering metabolites of post-harvest fungicides in citrus with liquid chromatography/time-of-flight mass spectrometry and ion trap tandem mass spectrometry.

In this study, we benefit from the combination of liquid chromatography (LC)/time-of-flight (TOF) MS accurate mass measurements to generate elemental compositions of ions and LC/ion trap multiple MS (MSn) providing complementary structural information, which is useful for the elucidation of unknown organic compounds at trace levels in complex food extracts. We have applied this approach to investigate different citrus fruits extracts, and we have identified two post-harvest fungicides (imazalil and prochloraz), the main degradation product of imazalil ([M + H]+, m/z 257) and a non-previously reported prochloraz degradation product ([M + H]+, m/z 282). The database-mediated identification of the parent compounds was based on the generated elemental composition obtained from accurate mass measurements and additional qualitative information from the high resolution chlorine isotopic clusters of both the protonated molecules (imazalil, [M + H]+ 297.0556, <0.1 ppm error, 2-Cl; prochloraz, [M + H]+ 376.0381, 1.9 ppm error, 3-Cl) and their characteristic fragments ions (imazalil: m/z 255 and 159; prochloraz: m/z 308 and 266). The correlation between the structural information provided by ion trap MS/MS fragmentation pathways of the parent species and the TOF accurate mass elemental composition data of the degradation products were the key to elucidate the structures of the degradation products of both post-harvest fungicides. Finally, where standards were not available (prochloraz), further confirmation was obtained by synthesizing the proposed degradation product by acid hydrolysis of the parent standard and confirmation by LC/TOF-MS.

Chromatography, Liquid↗
PubMed2005

Quantitation of 13 azole fungicides in wine samples by liquid chromatography-tandem mass spectrometry.

A liquid chromatography-tandem mass spectrometry (LC-MS/MS) method has been developed for the direct quantitation of residues of 13 azole fungicides in wine and has been successfully applied to 103 wine samples. The method utilizing 25 transitions is highly sensitive and specific with centrifugation as the only sample work-up step. Precision was better than 14% and accuracy ranged between 80 and 120%. Quantitation limits (LOQs) ranged between 0.25 (penconazole) and 7.5 ng/mL (triadimefon). Since the LOQs achieved are at least four times lower than the maximum residue levels for azole-fungicides in wine prescribed, the method presented here can be conveniently used as a screening assay for azole-residues in wine samples.

Azoles↗
PubMed2004

Effect of fungicide iprodione on soil bacterial community.

The effect of the fungicide iprodione on soil bacterial communities was studied by treating two kinds of soils with different concentrations of iprodione. Degradation rates of iprodione in sterile and unsterile soils were also investigated. Residues of iprodione were measured by using high-performance liquid chromatography (HPLC) and a change of bacterial communities was performed with denaturing gradient gel electrophoresis (DGGE) by counting the 16S rDNA band on DGGE patterns. The degradation rate of iprodione was slower in sterile soil than in unsterile soil in both Da-Hu sandy loam and Kuan-Shi loam. After treatment with fungicide, soil bacterial communities were changed and recovered rapidly to the original status when incubated at a lower temperature (15 degrees C) and a lower iprodione concentration (5 microg/g). At the same temperature but with more iprodione (50 microg/g) added, the soil bacterial community increases slowly and regains the original status slowly. However, when incubated at the higher temperature (30 degrees C), the soil bacterial community is more complex than that at the lower temperature. The response of the soil bacterial community to the iprodione is faster at the higher than at the lower temperature. At 30 degrees C and with 50 microg/g iprodione, the amounts of soil bacterial communities increased quickly but cannot be reduced to the original status after incubation for 23 days.

Aminoimidazole Carboxamide↗