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PubMedDate not supplied

Determination of benzimidazole fungicides in soil samples using microwave-assisted micellar extraction and liquid chromatography with fluorescence detection.

A simple and fast analytical method was developed for the determination of benzimidazole fungicides (benomyl, carbendazim, thiabendazole, and fuberidazole) in soil samples. The analytes were extracted from the soil samples by means of conventional microwave-assisted extraction, using the non-ionic surfactants polyoxyethylene 10 lauryl ether (POLE) and oligoethylene glycol monooalkyl ether (Genapol X-080) as extractants. Determinations were made by using liquid chromatography with direct fluorescence detection. The use of an analytical column Symmetry C-18 offered short retention times of analytes without the need of any pH regulators with mobile phase methanol-water (50 + 50, v/v). The best results were obtained using 5% (v/v) POLE as extractant with recoveries of the fungicides in spiked soil samples between 71 and 105%. The results were compared with those obtained when Soxhlet extraction was applied to the same soil samples.

Benzimidazoles↗
PubMedDate not supplied

Determination of nabam fungicide in crops by liquid chromatography with postcolumn reaction detection.

The ethylenebisdithiocarbamate (EBDC) fungicide, nabam, was determined in several crop matrixes using liquid chromatography with postcolumn reaction detection. After separation by micellar liquid chromatography, nabam (EBDC sodium salt) was acid hydrolyzed to ethylenediamine and fluorigenically labeled with o-phthalaldehyde-mercaptoethanol (OPA-MERC). Standard curves were linear from the detection limit of ca 1 ng to 1000 ng. Nabam was recovered in high yield (89 plus or minus 7.7%) over a range of concentrations (0.1 to 20 ppm) from fortified samples of papaya, lettuce, cucumber, spinach, and applesauce using a simple extraction method. Efforts to convert the more popular EBDC fungicides, maneb and mancozeb, to nabam are discussed.

Cetylpyridinium↗
PubMedDate not supplied

Residues of insecticides, fungicides, and herbicides on Ontario-grown vegetables, 1980-1985.

Between 1980 and 1985, 354 composite vegetable samples representing 9 vegetable commodities were collected from farm deliveries to the market place in Ontario, Canada. All samples were analyzed for insecticides, 275 for fungicides, and 135 for herbicides. The analyses included organochlorine, organophosphorus, synthetic pyrethroid, and N-methylcarbamate insecticides; dithiocarbamate, acylalanine, phthalimide, dicarboximide, and other fungicides; and, chlorophenoxy acid, chlorobenzoic acid, bipyridilium, phenylurea, carbamate, and other herbicides. The commodities tested included asparagus, beans, carrots, cauliflower, cucumbers, onions, potatoes, sweet corn, and tomatoes. In most samples, pesticide residues were below the detection limits (i.e., 0.005 to 0.1 mg/kg), and most of the positive findings were a fraction (i.e., less than 1 to 20%) of the maximum residue limit (MRL) permitted for each commodity under the Canadian Food and Drugs Act and Regulations. A small number of samples had residues that exceeded the MRL, and these involved aldicarb and linuron on potatoes and chlorobromuron on carrots.

Fungicides, Industrial↗
PubMed1979

[Rhizospheric organism under the influence of environmental pollution. II. Physiologic efficiency of the microbial biocenosis in fungicide containing soil (author's transl)].

Measuring the potential soil respiration according to the incubator method allows the physiological performance of the celluloytic microflora to be determined. Laboratory tests were carried out to analyse catabolic processes after soil samples had been enriched with native cellulose + fungides. As the temporary capacity of mineralization primarily induced by the substrate invariably gives rise to a substrate-specific "change in position" in the microbial biocenosis, the measured values cannot furnish a parameter for microbiological comparisons of the soil content. Preliminary analyses provided information on the processes of depolymerisation of various C-sources and characterized the celluloysis as well as the order of respiration of its monomer. The rising respiration curve markedly drops off after 12 days, because with the CO2 development at its maximum, total and partial respiration alternate, a phenomenon that was verified in soils incubated with glucose 14C (Keefer and Mortensen, 1963; Macura, 1963; Simonart and Mayaudon, 1958). The test results obtained with fungicide-treated soils (dithiocarbamine acid derivatives) allow the conclusion that the fungicides exercise a varying influence: in the cellulolysis the activity of the cellulase systems is reduced depending on the active substance and concentration, but what is surprising is that respiration is stimulated; this applies to amounts of pesticides being 0.75 and 1.5 times the practical quantity applied. Nor have the "dissociation tests" with cellobiose, which is supposed to be the final link of celluloysis, shown any inhibition of the 1.4--glucodimerase or high respiration values comparable with the glucose metabolism. Tests with cellulases (Cx with dimerase function, Messrs. Roehm and Haas, Darmstadt), which are at present being carried out, are expected to support these observations experimentally. Investigations intended to clarify whether an additional administration of Mn2+ and Fe3+ in the presence of Maneb and Ferbam permits interference with possible adsorption and exchange processes have not yet yielded any generally valid results. The results of the open-field investigations also tend to indicate that the mentioned dithio-carbamates determine the magnitude and the extent of the physiological and CO2-ecological processes to a varying degree; it can be seen that a remarkable "capacity fo compensation" is discernible in the succession of the investigated phases of soil-physiological processes which we tried to clarify.

Bacteria↗
PubMed1997

Allergic contact dermatitis from a lawn care fungicide containing dyrene.

Lawn care chemicals are frequently blamed when skin rashes occur in lawn care workers, although proof of a cause-and-effect relationship is often lacking. A lawn care worker developed severe dermatitis of the hands, arms, face, and neck shortly after his company started using a new fungicide. Patch-testing proved that the dermatitis was caused by a contact allergy to Dyrene, the active fungicidal chemical.

Adult↗
PubMed1998

Fertility among a cohort of male sawmill workers exposed to chlorophenate fungicides.

The purpose of this study was to determine whether exposure to chlorophenate fungicides and their dioxin contaminants is associated with male infertility among sawmill workers. The study was conducted using fertility data compiled from 26,487 sawmill workers in 14 British Columbian sawmills. Our analysis was restricted to workers who had been employed for at least 1 continuous year between 1950 and 1985 and to live-births born at least 1 year after the initiation of employment in the period 1955-1988. We assessed fertility trends by internal comparison using Mantel-Haenszel rate ratios and by calculating standardized fertility ratios using an external and an internal reference population. We identified 19,684 births in the study period. Initially, both external and internal analyses showed that sawmill workers from mills using chlorophenates had lower fertility than workers employed in mills not using chlorophenates. After controlling for time since first hire, however, we found no inverse relation between cumulative exposure to chlorophenate fungicides and fertility. Based on the results of our study, there is little evidence for a reduction in fertility among chlorophenate-exposed sawmill workers in British Columbia. The analyses indicate the importance of time since hire as a potentially strong confounder in this type of investigation.

Adult↗
PubMed2004

Synthesis and determination of the absolute configuration of fugomycin and desoxyfugomycin: CD spectroscopy and fungicidal activity of butenolides.

The dibromoalkenes (S)-3 and (R)- and (S)-4 are intermediates in the syntheses of the naturally occurring fungicidal butenolides fugomycin (1) and desoxyfugomycin (2), respectively. The stereoselective bromine-lithium exchange that leads to the carbenoid 12 and the vinyllithium reagent 17 a on the one hand, and palladium-catalyzed coupling reactions of the dibromoalkene 3 and the bromolactone 22 on the other are key steps en route to the butenolides 1 and 2. The chiral building blocks (S)-3, (R)-4, and (S)-4 are readily available from (R)-isopropylideneglyceraldehyde 5, isobutyl (R)-lactate 6 a, and ethyl (S)-lactate 6 b, respectively. The synthetic procedure adopted here permits the absolute configuration of the natural products fugomycin (1) and desoxyfugomycin (2) to be assigned by comparison of their chiroptical properties with those of the synthetic products. The CD spectra of the bromolactone 22, calculated by two different density functional methods (TDDFT, DFT/MRCI), are found to be in good agreement with the measured spectra. On the basis of these calculations, the two CD bands observed could be assigned to n-pi* and pi-pi* transitions, respectively. Fugomycin (1) and the synthetic butenolide 20 displayed high fungicidal activity against botrytis in greenhouse experiments, whereas the saturated lactone 21 was practically inactive.

4-Butyrolactone↗
PubMed2002

Evaluation of the aneugenic potential of the fungicide Ferbam in mice.

Ferbam, a potent dithiocarbamate fungicide is used as a protectant against a wide variety of fungal diseases in fruits, vegetables, and ornamental plants. The wide-spread use of this chemical is likely to pollute the environment. Hence, it was planned to test the possible genotoxicity of Ferbam through its aneugenic potential in the in vivo mouse (Mus musculus) test system. Four different doses of Ferbam, namely, 7.5, 15.0, 30.0, 60.0 mg/kg body weight were administered orally to mice Mus musculus suspended in gum tragacanth representing, respectively, 1/16, 1/8, 1/4;, 1/2 th of the LD50 value. They were sacrificed at 6-, 12-, 24-, and 48-h intervals along with a distilled water negative control at 2 mg/kg body weight. Colchicine treated animals were used as positive controls. Bone marrow preparations were made following the standard Hypotonic flame dry Giemsa staining technique to study the dose and time yield effect of Ferbam. The aneugenic potential was evaluated for C-mitotic effects by scoring the mitotic index, c-mitoses frequency, anaphase reduction, and hyper/hypodiploidy induction. Ferbam showed a significant increase in the mitotic index and C-mitoses effects and anaphase decreased at the highest doses of 30 and 60 mg/kg at 12- and 24-h intervals. Colchicine induced significant effects in all the aneugenic parameters observed at all the time intervals. There was no significant induction of either hyperdiploidy or hypodiploidy by Ferbam, unlike colchicine, indicating that the fungicide Ferbam is not aneugenic in the mouse test system.

Anaphase↗
PubMed1984

Aflatoxin contamination of maize kernels before harvest. Interaction of Aspergillus flavus spores, corn earworm larvae and fungicide applications.

Two maize (Zea mays L.) hybrids with varying degrees of resistance to damage by corn earworm (CEW) (Heliothis zea Boddie) were grown in Iowa, Georgia, and Missouri. Treatments included: introduction of Aspergillus flavus Link ex. Fr. spores onto newly-emerged silks, application of a fungicide as an aqueous spray onto test ears during the first three weeks after flowering, infestation of ears with CEW eggs, and combinations of these variables. CEW larvae were collected from developing ears and examined for the presence of internal A. flavus group propagules. Aflatoxin levels were determined in mature kernels. Toxin concentrations exhibited a distinct regional variation with relatively high levels in Georgia samples, intermediate concentrations in Missouri kernels and low levels in Iowa samples. No treatment effects were noted in Georgia samples but introduction of A. flavus and CEW increased toxin accumulation in Missouri kernels. Although the CEW-susceptible hybrid exhibited a trend towards increased damage by the insect, no treatment-related differences were observed in the presence of the fungus in larvae or in aflatoxin contamination. Fungicide applications did not significantly reduce aflatoxin levels in mature kernels.

Aflatoxins↗
PubMed1980

The effect of fungicides on survival of the crayfish plague fungus, Aphanomyces astaci, Oomycetes, growing on fish scales.

Zoospores from the crayfish plague fungus Aphanomyces astaci could germinate and grow in vitro on scales of Salmo salar. The fungicidal activity of different compounds was tested against the fungus growing on fish scales as well as in lake water. Malachite green was the most effective fungicide, but scale mucus protected the fungus from this compound to some extent. For complete inhibition of spore germination in scale mucus 2 mg1-1 was required compared to 1 1 mg1-1 in lake water.

Animals↗
PubMed1976

Effects of the herbicide 2,4-DB and fungicide captan on reactions of mitochondria and chloroplasts.

The effects of the herbicide 4(2,4-dichlorophenoxy)butyric acid (2,4-DB) and fungicide N-(trichloromethyltio)-4-cyclohexene-1,2-dicarboximide (captan) on electron transport processes of mitochondria and chloroplasts have been investigated. Chloroplasts, isolated from spinach leaves (Spinacia oleracea L.), were treated with pesticide prior to the addition of electron acceptor and ADP. White potato (Solanum tuberosum L.) mitochondria were either incubated with pesticide before the addition of substrate, or they were treated with pesticide after the addition of substrate and ADP. Captan inhibited oxidation of malate by mitochondria and acted as an uncoupler. With succinate as sunstrate captan was found to stimulate state 4 respiration, as substrate captan was found to stimulate state 4 respiration, with the loss of coupled phosphorylation only at higher concentrations of fungicide. The herbicide 2,4-DB appeared to be 5 to 10 times less effective than captain. Both compounds inhibited phosphrylation-coupled succinate oxidation at higher concentrations and malate-coupled phosphorylation at lower concentrations. They acted as inhibitors of NADH-cytochrome c reductase. Both pesticides inhibited noncyclic electron transport in chloroplasts. The rate of ferricyanide reduction in the presence and absence of phosphorylating agents was reduced, and although the rate of ATP generation was reduced also, the P/2e ratio was not changed much under the influence of pesticides.

Butyrates↗
PubMed1993

The fungicidal effect of human lactoferrin on Candida albicans and Candida krusei.

Five oral isolates each of Candida albicans and Candida krusei were studied for their sensitivity to the fungicidal effect of human lactoferrin. Significant inter- and intraspecies variations were observed and with most isolates the sensitivity of C. krusei to lactoferrin was greater than that of C. albicans. Fungicidal activity of lactoferrin was dose-dependent and observable only with the iron-free form of the molecule (apo-lactoferrin). Iron-saturated lactoferrin was ineffective against all isolates. Supernatant protein assays and scanning electron microscopy indicated cell surface alterations--leakage of proteins and formation of surface blebs--only in those Candida isolates that were sensitive to apo-lactoferrin. As lactoferrin is a common, non-immune, mucosal defence protein, its varying mode of action against C. albicans and C. krusei may be related to their different oral carriage rates.

Analysis of Variance↗
PubMed1994

Induction, suppression and inhibition of multiple hepatic cytochrome P450 isozymes in the male rat and bobwhite quail (Colinus virginianus) by ergosterol biosynthesis inhibiting fungicides (EBIFs).

Ergosterol biosynthesis inhibiting fungicides (EBIFs) have complex effects on the hepatic microsomal monooxygenase systems of vertebrate species, having been described as mixed inducers and inhibitors of cytochrome P450. In the current study, we examined the effects of two EBIFs in clinical use, clotrimazole and ketoconazole, and two agricultural EBIFs, propiconazole and vinclozolin, on hepatic monooxygenase activities and P450 apoprotein expression in the male Sprague-Dawley rat and the male bobwhite quail. EBIFs produced Type II binding spectra with hepatic microsomes from both species and were effective inhibitors of methoxyresorufin O-demethylase, an activity selective for P450 isozymes in gene family 1. However, the EBIFs varied widely in their effectiveness as inducers of P450 isozymes in gene families 1, 2, 3 and 4, both within the same species and between species. In the rat, clotrimazole was the most effective inducer, increasing expression of CYP 3A isozymes over 450-fold, CYP 2B1/2 30-fold and CYP 1A1/2 12-fold and suppressing expression of CYP 2C11 nearly 70%. By contrast, in the quail, clotrimazole was the least effective inducer. In quail, vinclozolin and propiconazole elevated total P450 content 10- and 7-fold, respectively. The induction response also appeared to be mixed, but in this case consisted of a 5-fold induction of P450s in gene family 1A, a 3-fold induction of P450s in gene family 3A and 4A, and induction of protein(s) from gene family 2, cross-reactive with antisera against rat CYP 2C11 and CYP 2A1. A protein that was cross-reactive with antibodies raised against rat CYP 2B1 was decreased with EBIF treatment. In conclusion, EBIFs have complex patterns of induction, suppression and inhibition of cytochrome P450 isozymes in both mammals and birds, which vary according to both the fungicide and the species.

Animals↗
PubMedDate not supplied

An investigation of the bactericidal and fungicidal effects of certain disinfectants by use of a capacity test.

The bactericidal and fungicidal effects of five disinfectants and one combination of two disinfectants were tested using a modified Kelsey-Sykes method in which living microorganisms suspended in a sterilized yeast suspension ("dirty" conditions) and in sterile distilled water ("clean" conditions) were added to the disinfectants in three stages. Six bacteria and two fungal organisms were employed as test microbes. Results showed that formaldehyde was virtually inactive at the dilution tested (1/50), whereas phenol and the combination propylene-phenoxetol + benzalkonium chloride were moderately effective, the latter compound being better. Glutaraldehyde was manifestly the most effective of the disinfectants tested, followed by tricresol. At a 1/50 dilution, chloramine proved to have a surprisingly strong fungicidal effect on Candida albicans and Aspergillus fumigatus under "dirty" conditions, whereas the same fungal organisms proved rather resistant to chloramine under "clean" conditions. The same was demonstrated--though less markedly--when higher dilutions of chloramine were used. The search for an explanation is still in progress. At relatively high dilutions, chloramine also proved quite effective against most of the test bacteria, especially under "clean" conditions. It is recommended that the yeast suspension be replaced by normal horse serum 20% v/v when testing the efficacy of chloramine against fungal strains under "dirty" conditions.

Bacteria↗
PubMed2006

Stereoselective synthesis and fungicidal activities of (E)-alpha-(methoxyimino)-benzeneacetate derivatives containing 1,3,4-oxadiazole ring.

Fifteen novel (E)-alpha-(methoxyimino)-benzeneacetate derivatives, the analogues of strobilurins, which contain two pharmacophoric substructures of (E)-methyl methoxyiminoacetate moiety and 1,3,4-oxadiazole ring were stereoselectively synthesized. It was first found that the coupling reaction could give stereoselectively the key intermediate (E) and (Z)-methyl 2-(hydroxyimino)-2-o-tolylacetate 2 with a ratio of 14:1. The preliminary bioassays indicated that all the compounds 1 showed potent fungicidal activity against Rhizoctonia solani, Botrytis cinereapers, Gibberella zeae, Physalospora piricola and Bipolaris mayclis, and all of the tested compounds 1a-1o had more potent fungicidal activities against R. solani than Kresoxim-methyl.

Acetates↗
PubMed2005

Quantitative changes in the digestive gland cells of the snail Helix aspersa after exposure to the fungicide copper oxychloride.

This study investigated the relationship between accumulated copper in the digestive gland of Helix aspersa, after exposure to the fungicide copper oxychloride, and quantitative changes in the digestive gland cells of this snail. Snails were exposed to 80 and 240 microg g(-1) copper oxychloride for 6 weeks. Histological sections of digestive glands were analyzed by means of computer-assisted image analysis. Results indicate that copper is strongly accumulated in the digestive gland and that this organ is the main site of copper accumulation in the snail body. Also, as a result of copper accumulation in the digestive gland, measurable changes in epithelium cell height and area of this organ occur. In the case of cell height, these changes are dose-related. It is concluded that changes in digestive gland cells, as a result of copper oxychloride exposure, may possibly serve as biomarkers of exposure to this fungicide.

Animals↗
PubMed1999

A critical comparison of the hemolytic and fungicidal activities of cationic antimicrobial peptides.

The hemolytic and fungicidal activity of a number of cationic antimicrobial peptides was investigated. Histatins and magainins were inactive against human erythrocytes and Candida albicans cells in phosphate buffered saline, but displayed strong activity against both cell types when tested in 1 mM potassium phosphate buffer supplemented with 287 mM glucose. The HC50/IC50 ratio, indicative of the therapeutic index, was about 30 for all peptides tested. PGLa was most hemolytic (HC50 = 0.6 microM) and had the lowest therapeutic index (HC50/IC50 = 0.5). Susceptibility to hemolysis was shown to increase with storage duration of the erythrocytes and also significant differences were found between blood collected from different individuals. In this report, a sensitive assay is proposed for the testing of the hemolytic activities of cationic peptides. This assay detects subtle differences between peptides and allows the comparison between the hemolytic and fungicidal potency of cationic peptides.

Amino Acid Sequence↗
PubMed2000

Fungicidal activity of natural and synthetic sesquiterpene lactone analogs.

Fungicidal activity of 36 natural and synthetic sesquiterpene lactones with guaianolide, trans, trans-germacranolide, cis, cis-germacranolide, melampolide, and eudesmanolide carbon skeletons was evaluated against the phytopathogenic fungi Colletotrichum acutatum, C. fragariae, C. gloeosporioides, Fusarium oxysporum, Botrytis cinerea, and Phomopsis sp. Dose-response data for the active compounds dehydrozaluzanin C, dehydrocostuslactone, 5alpha-hydroxydehydrocostuslacone, costunolide, and zaluzanin C are presented. A new 96-well microbioassay procedure for fast and easy evaluation of antifungal activity was used to compare these compounds with commercial fungicide standards. Some structure-activity conclusions are also presented.

Antifungal Agents↗