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PubMed2002

Liquid chromatographic method development for determination of fungicide epoxiconazole enantiomers by achiral and chiral column switching technique in water and soil.

High-performance liquid chromatography (HPLC) in both chiral isocratic and achiral-chiral column switching mode was employed for optimization of separation conditions, separation and determination of fungicide epoxiconazole in real samples. Two enantiomers of commercially available triazole fungicide epoxiconazole (BAS 480 F), first registered in 1993, were resolved for the first time on a microcrystalline cellulose triacetate (MCTA). A low-cost home-packed chiral column (150x3 mm, 15-25 microm, MCTA, Merck) enabled baseline enantiomeric resolution of two enantiomers of the fungicide epoxiconazole produced commercially. The effects of concentration of organic modifiers (methanol, ethanol) in mobile phase, flow-rate and temperature were studied. The isocratic chiral HPLC method allows determination of the enantiomers in tap and surface water within the range 1-1000 mg/l by direct injection (20 microl) of the sample. Using the achiral (C18)-chiral (MCTA) column-switching technique and 1-ml sample volume, injection of 0.050 mg/l of epoxiconazole enantiomers can be conveniently determined by UV detection at 230 nm. The same method applied to methanolic soil extracts allows determination of 0.2 mg/kg of epoxiconazole enantiomers in addition to the other 10 commonly used pesticides in fortified soils.

Calibration↗
PubMed2003

Multiresidue method for fourteen fungicides in white grapes by liquid-liquid and solid-phase extraction followed by liquid chromatography-diode array detection.

A quantitative, selective and sensitive HPLC method for the analysis of 14 fungicides in white grapes for vinification is described. The proposed method is based on liquid-liquid extraction (LLE) and solid-phase extraction (SPE) followed by liquid chromatography and diode array detection (HPLC-DAD). Dichloromethane-acetone (75:25, v/v) was the most appropriate solvent mix for extracting fungicides in white grapes. Silica cartridges resulted the most appropriate for extract purification purposes. Quality parameters of the proposed multiresidue method presented good recovery (ca. 85% for almost all target compounds) and precision (between 1.5 and 16%), and detection limits lower than maxima residual limits set by the 76/895/ECC and 90/642/ECC Directive. Five different white grapes for vinification produced in Rias Baixas area in Galicia (NW Spain) were analyzed in order to assess the performance of the method with real samples and to determine whether the concentration of the pesticides used exceed their maxima residue levels (MRLs). Results showed that grape concentrations for those identified fungicides were lower than those established by European legislation.

Chromatography, High Pressure Liquid↗
PubMed2003

Coupling solid-phase microextraction and high-performance liquid chromatography for direct and sensitive determination of halogenated fungicides in wine.

A solid-phase microextraction (SPME) method coupled to high-performance liquid chromatography with diode array detection (HPLC-DAD) for the analysis of six organochlorine fungicides (nuarimol, triadimenol, triadimefon, folpet, vinclozolin and penconazole) in wine was developed. For this purpose, polydimethylsiloxane-divinylbenzene-coated fibers were utilized and all factors affecting throughput, precision, and accuracy of the SPME method were investigated and optimized. These factors include: matrix influence, extraction and desorption time, percentage of ethanol, pH, salt effect and desorption mode. The performed analytical procedure showed detectability ranging from 4 to 27 microg l(-1) and precision from 2.4 to 14.2% (as intra-day relative standard deviation, RSD) and 4.7-25.7% (as inter-day RSD) depending on the fungicide. The results demonstrate the suitability of the SPME-HPLC-DAD method to analyze these organochlorine fungicides in red wine.

Chromatography, High Pressure Liquid↗
PubMed2002

Sorptive behavior of the phenylamide fungicides, mefenoxam and metalaxyl, and their acid metabolite in typical Cameroonian and German soils.

Laboratory soil sorption experiments were conducted on mefenoxam, formulated metalaxyl (F-metalaxyl), pure metalaxyl (P-metalaxyl) and metalaxyl acid metabolite to elucidate differences in their sorptive behaviour on typical Cameroonian forest soil (sand clay loam, pH 4.8 and 3.01% OC) and German soil (sandy loam, pH 7.2, 1.69% OC) using a batch equilibrium method. The data obtained on all test chemicals conformed to linear and Freundlich adsorption isotherms. The Langmuir equation failed to describe the sorption of the substances tested. All substances were adsorbed to a greater extent by the Cameroonian soil. The average percentage adsorptions for mefenoxam, F-metalaxyl, P-metalaxyl and the acid metabolite on the Cameroonian soil were 27.8%, 28.3%, 31.8% and 46.8% respectively while for the German soil they were 21.7%, 21.5%, 24.7% and 9.8% respectively. The KD and KF parameters and the Freundlich exponential term (1/n) were low, indicating that the interactions between soil particles and the fungicides were weak. The sorption parameters were lower in the German soil. P-metalaxyl exhibited a higher adsorption capacity than F-metalaxyl in both soils. Mefenoxam and F-metalaxyl exhibited similar sorption parameters in soils, whereas those of P-metalaxyl and acid metabolite differed. Differences observed in the adsorption between the two soils could be attributed to their properties. Desorption studies revealed that the adsorbed fungicides were not firmly retained by soil particles and their adsorption was reversible. Desorption of adsorbed mefenoxam, P-metalaxyl and of the acid metabolite from German soil was almost completely reversible with percentage desorption rates of more than 91.0%, whereas the rate for F-metalaxyl was 74.1%. All compounds exhibited some resistance to desorption from the Cameroonian soil, with percentage desorption rates less than 77.0%. Therefore if degradation in the soil is slow the fungicides described have a potential to leach to lower soil horizons.

Absorption↗
PubMedDate not supplied

Effects of three fungicides alone and in combination on glutathione S-transferase activity (GST) and cytochrome P-450 (CYP 1A1) in the liver and gill of brown trout (Salmo trutta).

In order to evaluate the gill glutathione S-transferase (GST) activity as a biomarker of effect of fungicide exposure in juvenile brown trout (Salmo trutta), the fungicides propiconazole [(R,S)-1-[2-(2,4-diclophenyl)-4-propyl-1,3-dioolan-2-ylmetyl]-1H-1,2,4-triazole] and fenpropimorph [(+/-)-cis-4-[3-(4-tert-butylphenyl)-2-metyl propyl]-2,6 dimetylmorfolinc] were administrated in the water separately and together in a static system (80 microg/l for each pesticide) for 5 days. The combined fungicides gave a significant decrease in gill GST activity towards 1-chloro-2,4-dinitrobenzene (CDNB), whilst hepatic GST-activity was not significantly changed. Furthermore, continuous exposure to 540 ug/l thiabendazole[2-(thiazol-4'-yl)benzimidazole] in a flow-through system for 4 days significantly increased the gill glutathione S-transferase (GST) activity towards CDNB, whilst hepatic GST and cytochrome P450 (CYP 1A) activities were not increased by the treatment.

Animals↗
PubMed1996

Mechanisms of fungicide resistance in phytopathogenic fungi.

The disciplines traditionally used to investigate the mode of action of fungicides have been biochemistry and physiology. Over the past decade, classical and molecular genetics have been brought to bear on this problem with increasing success. Recently, genetic studies of fungicide resistance have led to advances in our understanding of the site of action of chemicals active against plant pathogens and, in some cases, to an appreciation of additional mechanisms of resistance to fungicide action.

Biotechnology↗
PubMed2002

An osmosensing histidine kinase mediates dicarboximide fungicide resistance in Botryotinia fuckeliana (Botrytis cinerea).

A two-component histidine protein kinase gene, homologous to os-1 from Neurospora crassa, was cloned and sequenced from a single ascospore isolate of Botryotinia fuckeliana. A series of nine spontaneous mutants resistant to dicarboximide fungicides was selected from this strain and characterized with respect to fungicide resistance and osmotic sensitivity. Genetic crosses of the mutants with an authentic Daf1 strain showed that the phenotypes mapped to this locus. Single point mutations (seven transitions, one transversion, and one short deletion) were detected in the alleles of the nine mutants sequenced. The mutational changes were shown to cosegregate with the dicarboximide resistance and osmotic sensitivity phenotypes in progeny obtained from crossing selected resistant strains with a sensitive strain. All mutations detected are predicted to result in amino acid changes in the coiled-coil region of the putative Daf1 histidine kinase, and it is proposed that dicarboximide fungicides target this domain.

Amino Acid Sequence↗
PubMed2006

Influence of pH on the stereoselective degradation of the fungicides epoxiconazole and cyproconazole in soils.

Many pesticides are chiral and consist of two or more enantiomers/stereoisomers, which may differ in biological activity, toxicity, effects on nontarget organisms, and environmental fate. In the last few years, several racemic compounds have been substituted by enantiomer-enriched or single-isomer compounds ("chiral switch"). In this context, the stereoselective degradation in soils is an important part of a benefit-risk evaluation, but the understanding of the environmental factors affecting the chiral preferences is limited. In this study, the stereoselective degradation of the fungicides epoxiconazole and cyproconazole was investigated in different soils, selected to cover a wide range of soil properties. The fungicides were incubated under laboratory conditions and the degradation and configurational stability of the stereoisomers were followed over time using enantioselective GC-MS with a gamma-cyclodextrin derivative as chiral selector. In alkaline and slightly acidic soils, the degradation of epoxiconazole was clearly enantioselective, whereas in more acidic soils, both enantiomers were degraded at similar rates (overall half-lives 78-184 d). The enantioselectivity, expressed as ES = (k(i) - k(j))/ (k(i) + k(j)), ranged from -0.4 in alkaline soils (faster degradation of enantiomer j) to approximately 0 in acidic soils (non-enantioselective), and showed a reasonably linear correlation with the soil pH. The four stereoisomers of cyproconazole (overall half-lives 5-223 d) were also degraded at different rates in the various soils, but only the stereoselectivities between epimers showed some correlations with pH, whereas enantioselectivities did not. Both fungicides were configurationally stable in soils, i.e., no enantiomerization or epimerization was observed. Correlations between pH and ES have previously been reported for other pesticides (metalaxyl, dichlorprop, mecoprop), but the presence or absence of such correlations is not obviously linked to the pathways of degradation. It can be assumed that different microorganisms and enzymes are involved in the primary degradation of these compounds, but on which level soil pH has an influence on ES remains to be investigated.

Epoxy Compounds↗
PubMed2004

Effect of fungicide residues on the aromatic composition of white wine inoculated with three Saccharomyces cerevisiae strains.

The effects of three fungicide residues (cyprodinil, fludioxonil, and pyrimethanil) on the aromatic composition (acids, alcohols, and esters) of Vitis vinifera white wines (var. Airén) inoculated with three Saccharomyces cerevisiae strains (syn. bayanus, cerevisiae, and syn. uvarum) are studied. The aromatic exponents were extracted and concentrated by adsorption-thermal desorption and were determined by gas chromatography using a mass selective detector. The addition of the three fungicides at different doses (1 and 5 mg/L) produces significant differences in the acidic fraction of the aroma, especially in the assays inoculated with S. cerevisiae, although the final contents do not exceed the perception thresholds. The lower quality wines, according to isomeric alcohol content [(Z)-3-hexen-1-ol and 3-(methylthio)propan-1-ol] are those obtained by inoculation with S. cerevisiae(syn. bayanus) and addition of cyprodinil. The addition of fungicides in the assays inoculated with S. cerevisiae (syn. bayanus) produces an increase in the ethyl acetate and isoamyl acetate contents, which causes a decrease in the sensorial quality of the wine obtained.

Acids↗
PubMed2004

Assessing N,N'-Dibutylurea (DBU) formation in soils after application of n-butylisocyanate and benlate fungicides.

N,N'-Dibutylurea (DBU) is a breakdown product of benomyl [methyl 1-(butylcarbamoyl)-2-benzimidazole carbamate], the active ingredient in Benlate fungicides, and has been proposed as one cause for crop damage that growers claim to have occurred from the use of Benlate 50 DF fungicide. This study assessed DBU formation upon (1). application of n-butyl-1-[(14)C]butylisocyanate (BIC), the immediate precursor to DBU formation, in four soils at two water potentials (0.03 and 0.1 MPa) and (2). application of benomyl butyl-1-(14)C-benomyl enriched Benlate DF and SP fungicides to two soils at various combinations of negative water potential (0.03 or 0.1 MPa) and temperature (23 or 33 degrees C). Parent compounds, metabolites, and (14)CO(2) were tracked using chromatographic analysis with radioassay and UV detection, liquid scintillation counting, and postextraction oxidation of the soil. At 0.03 MPa in all four BIC-treated soils, DBU formation was never detected. At 0.1 MPa, DBU was detected in two soils, but at concentrations <3.6 microg kg(-)(1) (0.3 wt % of applied BIC). In both soils treated with benomyl formulations, DBU formation was observed with only Benlate 50 DF application at 0.03 MPa and 23 degrees C, which was followed by rapid dissipation of DBU. The maximum concentration observed was 0.41 microg g(-)(1) (0.65 wt % of applied benomyl at 62.8 microg g(-)(1)), which is well below levels currently reported to cause adverse effects to plants. Combined benomyl and carbendazim half-lives in soils across treatments were 2-3 months. This study demonstrated that further production and accumulation of DBU in soils after Benlate application or from residual benomyl remaining in the soil are highly unlikely and that persistence of any DBU in soils is likely to be short-lived.

Benomyl↗
PubMed1999

Fungicide residues in strawberry processing.

The fate of three fungicides (dichlofluanid, procymidone, and iprodione) applied under field conditions was studied during strawberry processing to juice, wine, and jam. An untreated control was compared to raw material treated with fungicides according to recommended doses and to a sample with 6-fold higher application rates. The highest residue values were found in the pomace after pressing. Residue values in readily produced juices and fruit wines were very low and did not exceed legally required maximum residue levels. Generally, processing steps such as pressing and clarification diminished fungicide residues from 50 to 100%. If the whole fruit is processed, as in fruit preparations or jam, the residue levels remain higher due to missing processing steps.

Aminoimidazole Carboxamide↗
PubMed2000

Synthesis and fungicidal activity against Rhizoctonia solani of 2-alkyl (Alkylthio)-5-pyrazolyl-1,3,4-oxadiazoles (Thiadiazoles).

Some series of 2-alkyl (alkythio)-5-((4-chloro)-3-ethyl-1-methyl-1H-pyrazole-5-yl)-1,3, 4-oxadiazoles (thiadiazoles) were prepared as potential fungicides. Their fungicidal activity was evaluated against rice sheath blight, which is a major disease of rice in China. Structure-activity relationships for the screened compounds were evaluated and discussed. It was found that 5-(4-chloro-3-ethyl-1-methyl-1H-pyrazole-5-yl)-1,3, 4-thiadiazole-2-thione has the higher fungicidal activity.

Fungicides, Industrial↗
PubMed2001

Allergic contact dermatitis due to thiuram exposure from a fungicide.

A 49-year-old man developed a widespread eczematous eruption following contact with plants sprayed with a fungicide. Patch testing revealed a strong reaction to thiuram mix and several of the individual thiuram mix constituents. The fungicide contained tetramethylthiuram disulphide, a thiuram chemical. Thiurams are widely recognized as a cause of rubber-glove allergy; however, they are also used extensively in fungicides.

Dermatitis, Allergic Contact↗
PubMed2000

In vitro studies of cellular and molecular developmental toxicity of adjuvants, herbicides, and fungicides commonly used in Red River Valley, Minnesota.

Recent epidemiologic studies showed increased frequency of birth defects in pesticide applicators and general population of the Red River Valley, Minnesota. These studies further indicated that this crop growing area used more chlorophenoxy herbicides and fungicides than elsewhere in Minnesota. Based on frequency of use and known biology, certain herbicides, pesticide additives, fungicides, and mycotoxins are suspect agents. To define whether these agents affect developmental endpoints in vitro, 16 selected agrochemicals were examined using the MCF-7 breast cancer cell line. In the flow cytometric assay, cell proliferation in this estrogen-responsive cell line indicates xenobiotic-mediated estrogenic effects. Cell viability, morphology, ploidy, and apoptosis were incorporated in this assay. Data showed that the adjuvants X-77 and Activate Plus induced significant cell proliferation at 0.1 and 1 microg/ml. The commercial-grade herbicides 2,4-D LV4 and 2,4-D amine induced cell proliferation at 1 and 10 microg/ml. The reagent-grade 2,4-D products failed to induce proliferation over the same concentration range, suggesting that other ingredients in the commercial products, presumably adjuvants, could be a factor in these results. The fungicides triphenyltin and mancozeb induced apoptosis at concentrations of 4.1 microg/ml (10(-5) M) and 50 microg/ml, respectively. Triphenyltin also induced aneuploidy (C2/M arrest) at 0.41 microg/ml (10(-6) M). Data provide a mechanistic step to understanding human reproductive and developmental effects in populations exposed to these agrochemicals, and initiative to focusing limited resources for future in vivo animal developmental toxicity studies.

2,4-Dichlorophenoxyacetic Acid↗
PubMed2003

Triazole fungicide degradation in peaches in the field and in model systems.

The degradation of five triazole fungicides (cyproconazole, hexaconazole, penconazole, propiconazole, tebuconazole) in peaches was evaluated in field studies to establish whether at the preharvest interval the residue levels were below the legal limit established in Italy. All fungicides, except propiconazole, showed higher residues than the legal limits because of their high stability. In fact, some did not decrease at all (cyproconazole, penconazole, tebuconazole), while others decreased only in part. The increasing weight of the fruit during growth was the main factor leading to an apparent decrease in pesticide levels on a weight for weight basis. The trials on model systems showed that co-distillation and sunlight photodegradation were the main mechanisms leading to a decrease in triazole levels. Although these fungicides are systemic, they did not enter the fruit and all residues were only present in the peel.

Chromatography, Gas↗
PubMed2006

Residues of the fungicide famoxadone in grapes and its fate during wine production.

Famoxadone is a recently applied fungicide to vines that belongs to the oxazolidinedione family. The fate of famoxadone was studied by considering the decay ratio of this fungicide during the maturation of grapes and wine production. The main factors affecting the presence of fungicide residues such as fruit growth, photodegradation, evaporation, thermodegradation and co-distillation were studied with model systems. An experimental field was treated with a commercial product containing famoxadone at the recommended dose. After this application, residues of famoxadone were found in grapes at 0.27 +/- 0.06 mg kg(-1). In this field experiment, the half-life t(1/2) of famoxadone, which is described by pseudo-first-order kinetics (R2 = 0.74), was 18 +/- 6 days, resulting from the photodegradation. The famoxadone residue levels in grapes were below the established maximum residues level for Europe (2 mg kg(-1)), whilst levels in wine, carried out with and without maceration, were below the calculated limit of detection of the method.

Fermentation↗
PubMedDate not supplied

Residues of insecticides and fungicides on Ontario-grown vegetables, 1986-1988.

Between 1986 and 1988, 433 composite vegetable samples representing 16 commodities were collected from farm deliveries to the marketplace in Ontario, Canada. All samples were analysed for insecticides and fungicides. The analyses included organochlorine, organophosphorus, synthetic pyrethroid, and N-methylcarbamate insecticides and dithiocarbamate, dicarboximide, and organochlorine fungicides. The commodities tested included asparagus, beans, carrots, celery, cole crops, cucumbers, lettuce, onions, peppers, potatoes, radishes, rutabagas and tomatoes. In 64% of samples, no pesticide residues were identified to the limits of detection which ranged from 0.005 to 0.05 mg/kg. A further 22% had combined insecticide and fungicide residues below 0.1 mg/kg. Most of the positive findings were a fraction of the Maximum Residue Limit permitted for each commodity under the Canadian Food and Drugs Act and Regulation. Three samples (0.7%) had residues that exceeded the MRL. These involved diazinon and parathion on celery and chlorothalonil on peppers. While some commodities had no detectable residues others had measurable residues of up to three separate pesticides. The most were found on celery, lettuce and field tomatoes.

Food Analysis↗
PubMed1985

Residues analysis of post-harvest imidazole fungicides in citrus fruit by HPLC and GLC.

The determination of imazalil and prochloraz fungicide residues has been carried out by HPLC with an UV detector at 204 nm and by GLC with an electron capture detector (ECD). In both cases fungicide residues were extracted with hexane/acetone (90:10, v/v) after pH adjustment and purified by a liquid-liquid partitioning process. When HPLC was used for prochloraz and imazalil analysis, it was necessary to eliminate the interfering substances with a further clean-up process. This was also required when samples with low residue levels were analyzed by GLC. Recovery was always higher than 70%. The detection limit was 0.04 ppm for the HPLC method and 0.02 for the GLC method. Imazalil and prochloraz residues in "Washington Navel" oranges and "Hernandina" clementine fruits, dipped in a 1000 ppm fungicide solution, are reported.

Chromatography, Gas↗