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PubMed1984

An embryotoxicity study of the fungicide tridemorph and its commercial formulation Calixin.

Tridemorph (N-tridecyl-2,6-dimethylmorpholine), the active ingredient of the commercially formulated fungicide Calixin, is a teratogen in rats and mice. The no-effect level for embryotoxic effects was 27.5 mg/kg for mice and 20.6 mg/kg for rats. By contrast, when Calixin, which contains 83% tridemorph, was administered orally at dose levels of 0.156, 0.722, and 3.909 mg/kg, no embryotoxic effects were observed in two strains of rats. Our extensive investigations, carried out under exposure conditions resembling as closely as possible those reported in another study, did not reproduce the previous findings of teratogenicity of Calixin.

Abnormalities, Drug-Induced↗
PubMed2000

Effects of the fungicide copper oxychloride on the growth and reproduction of Eisenia fetida (Oligochaeta).

The article describes a laboratory experiment to determine the effect of copper oxychloride on the earthworm Eisenia fetida. Copper oxychloride was used because it is the most commonly used fungicide in South African vineyards but not much is known about its toxicity to earthworms. In an experiment lasting 8 weeks, newly hatched earthworms of the species E. fetida were exposed to copper oxychloride mixed into a urine-free cattle manure substrate. Four groups of 10 worms were used per concentration level (control (4.02), 8.92, 15.92, 39.47, 108.72, 346.85 mg Cu kg substrate(-1)). The following life-history parameters were measured: earthworm growth in consecutive weeks, survival rate, maturation time, cocoon production, reproduction success, total number of hatchlings produced, and incubation time. Earthworm growth and cocoon production were significantly reduced at copper oxychloride exposure concentrations of 8.92 mg kg(-1) and higher. Reproduction success in the 8.92 mg Cu kg substrate(-1) was highest. From an exposure concentration of 15. 92 mg Cu kg substrate(-1) and higher, there was a considerable impact of copper oxychloride on reproduction. This could be seen from a reduced reproduction success, a reduced mean and maximum number of hatchlings per cocoon, and a longer incubation time, indicating a strong effect of low copper oxychloride concentrations on this earthworm species.

Animals↗
PubMed2001

Evaluation of the fungicide manganese-zinc ethylene bis(dithiocarbamate) (mancozeb) for sublethal and acute toxicity to Eisenia fetida (Oligochaeta).

This article describes the outcome of laboratory experiments to determine the acute and sublethal effects of the fungicide mancozeb on the earthworm Eisenia fetida. Apart from a standardized acute test, young worms, 25 days old, were exposed to mancozeb mixed into a urine-free cattle manure substrate. Five groups of 10 worms each were used per concentration level (0, 8, 44 mg/kg substrate). The following life-history parameters were measured: growth in consecutive weeks over a 6-week period, survival rate, maturation time, cocoon production, hatching success of cocoons, number of hatchlings per cocoon, and incubation time of cocoons over another 4 weeks. The results indicated that mancozeb had no significant detrimental effect on either growth or reproduction of E. fetida at the recommended dose (8 mg/kg) or at an estimated environmental concentration (44 mg/kg). The findings do not support the hypothesis that avoidance response to mancozeb could serve as an indication of toxicity.

Animals↗
PubMed1996

Biotransformation of the fungicide chlorthalonil by glutathione conjugation.

The biotransformation of the nephrotoxic fungicide chlorthalonil (2,4,5,6-tetrachloroisophthalonitril) has been studied in the rat and in rat liver subcellular fractions. In rat liver cytosol, chlorthalonil was rapidly transformed to 4,6-bis(glutathion-S-yl)-2,5-dichloroisophthalonitril in the presence of glutathione in a reaction catalysed by glutathione S-transferases. 4-(Glutathion-S-yl)-2,5,6-trichloroisiphthalonitril was observed as an intermedite in the glutathione-dependent biotransformation of chlorthalonil. In the bile of rats dosed with chlorthalonil (0.18 mmol/kg, orally) 4,6-bis (glutathion-S-yl)-2,5-dichloroisophthalonitril was recovered as a minor metabolite. In rats, chlorthalonil was transformed to 4,6-bis (N-acetyl-cystein-S-yl)-2,5-dichloroisophthalonitril. This metabolite was excreted in small amounts in the urine of rats dosed orally with chlorthalonil (0.66 and 2.64 mmol/kg). In all experiments, a major part of the dose was recovered as unchanged chlorthalonil in feces. Oral administration of chlorthalonil (0.66 and 2.64 mmol/kg) resulted in a slight increase in the urinary excretion of gamma-glutamyltranspeptidase, indicative of nephrotoxicity. Other parameters indicative for renal proximal tubular damage (urinary glucose and protein excretion) were not changed by acute chlorthalonil administration. Very minor renal lesions were observed in chlorthalonil-dosed animals by histopathological examination.

Animals↗
PubMed2002

Comparative in vitro-in vivo percutaneous penetration of the fungicide ortho-phenylphenol.

The validity of in vitro and in vivo methods for the prediction of percutaneous penetration in humans was assessed using the fungicide ortho-phenylphenol (OPP) (log Po/w 3.28, MW 170.8, solubility in water 0.7 g/L). In vivo studies were performed in rats and human volunteers, applying the test compound to the dorsal skin and the volar aspect of the forearm, respectively. In vitro studies were performed using static diffusion cells with viable full-thickness skin membranes (rat and human), nonviable epidermal membranes (rat and human), and a perfused pig ear model. For the purpose of conducting in vitro/in vivo comparisons, standardized experimental conditions were used with respect to dose (120 microg OPP/cm(2)), vehicle (60% aqueous ethanol), and exposure duration (4 h). In human volunteers, the potentially absorbed dose (amount applied minus dislodged) was 105 microg/cm(2), while approximately 27% of the applied dose was excreted with urine within 48 h. In rats these values were 67 microg/cm(2) and 40%, respectively. In vitro methods accurately predicted human in vivo percutaneous absorption of OPP on the basis of the potential absorbed dose. With respect to the other parameters studied (amount systemically available, maximal flux), considerable differences were observed between the various in vitro models. In viable full-thickness skin membranes, the amount systemically available and the potentially absorbed dose correlated reasonably well with the human in vivo situation. In contrast the K(p)/maximal flux considerably underestimated the human in vivo situation. Although epidermal membranes overestimated human in vivo data, the species differences observed in vivo were reflected correctly in this model. The data generated in the perfused pig ear model were generally intermediate between viable skin membranes and epidermal membranes.

Administration, Cutaneous↗
PubMed1994

Circulatory failure caused by a fungicide containing iminoctadine and a surfactant: a pharmacological analysis in rats.

The fungicide Befran (BFR), containing iminoctadine as an active ingredient and polyoxyethylene alkylether (POEAE) as a surfactant, has been known to cause circulatory failure in human acute oral poisoning. We investigated separately the effects of iminoctadine, POEAE, and BFR on heart rate and blood pressure of rats and also on isolated atria and aortas. In isolated rat atria, iminoctadine produced positive chronotropic and inotropic responses. In contrast, POEAE produced negative chronotropic and inotropic responses. BFR produced no effects at low concentrations, but significant negative chronotropic and inotropic responses at high concentrations. In isolated rat aortas, iminoctadine produced remarkable vasodilative responses, but POEAE produced vasoconstrictive responses. BFR produced both vasodilative and vasoconstrictive responses. When intravenously administered to anesthetized rats, iminoctadine produced hypotension and tachycardia in a dose-dependent manner. POEAE produced significant hypotension and slight bradycardia. BFR, at low doses, produced hypotension without elevation of heart rate. At high doses, it produced significant hypotension and tachycardia. From these results, it can be concluded that severe hypotension induced by BFR is due mainly to the vasodilative effect of iminoctadine and partly to the cardio-suppressive effect of POEAE.

Animals↗
PubMed1990

Ethylenethiourea (ETU) in relation to use of ethylenebisdithiocarbamate (EBDC) fungicides.

Degradation of ethylenebisdithiocarbamate fungicides (EBDCs) is known to produce ethylenethiourea (ETU). This article reviews the literature available on the toxicology of EBDCs and ETU, the sources in plants and persistence of ETU, and its formation during heat treatment of plant products. Detoxification techniques developed are mentioned, and Maximum Residue Limits and the results of monitoring studies are given for several countries. Some aspects of the methods of analysis are discussed. Although EBDCs have in the past been regarded as relatively harmless, data on their subchronic and chronic toxicity indicate that these toxicological features should not be ignored. ETU has low acute toxicity but possesses carcinogenic, goiterogenic, teratogenic, and mutagenic activity in animal tests. The most prominent aspect of its toxicology is its action on the thyroid gland, which causes hyperplasia and a decrease in thyroid hormone levels. It is a potent teratogen in pregnant rats after either acute exposure or administration throughout organogenesis, inducing a wide spectrum of malformations to the progeny. The teratogenic potential is specific to rat, whereas administration to pregnant mouse, hamster, guinea pig, and cat causes limited or no teratogenicity, except at very high dose levels. The mutagenicity of ETU has not been clearly established, although some data exist that indicate that it indeed has mutagenic potential. ETU can react with nitrites to form N-nitroso-ETU, which is a mutagenic and teratogenic compound. Most of the ETU present in fresh agricultural products treated with EBDCs arises from the presence of ETU in formulations. Surface deposits of EBDCs on plants may be a secondary source. ETU may also be taken up by plants from the soil following the breakdown of EBDCs, but conflicting results have been obtained on this phenomenon. ETU on plant surfaces undergoes subsequent degradation. Although small amounts may persist up to 30 d after spraying, there is no indication that it accumulates in plants. Initial findings that ETU is formed during the heat processing of EBDC-treated foods are confirmed by the more recent literature. However, the variability of the results indicates a wide range of conversion due to processing. Boiling of spinach, pears, grapes, tomatoes, and wheat, treated with different EBDCs, resulted in 3-30% conversion to ETU. Apple juice, dried pomace, and applesauce contained more ETU than the EBDC-treated apples, from which these products were produced. This was also true for tomato juice and canned whole tomatoes. ETU may be produced in the smoke of tobacco containing high EBDC residues.(ABSTRACT TRUNCATED AT 400 WORDS)

Animals↗
PubMed1985

Dithiocarbamate fungicides decrease histochemical reactivity of cholinesterases in the gut wall of the rat.

The toxicity of dithiocarbamate fungicides is poorly known, especially in the autonomic nervous system. Male Wistar rats were given tetraethylthiuramdisulfide (DSF), maneb, and zineb as a suspension in saline i.p. 200 mg/kg daily for 4 d. Rats received a similar dose of ethylenethiourea (ETU) as a solution in saline i.p., and the control rats received a corresponding volume of saline i.p. After decapitation, pieces of ileum were taken, and the enzyme histochemical reactivity for the acetylcholinesterase (AChE) and for the nonspecific cholinesterase (nsChE) in the ilea of the treated and control animals was studied. The reaction intensities in the samples were estimated by eye using a scale from 0 (no reaction product) to 3+ (maximal reaction). DSF was used as an internal standard. Controls showed the maximal reaction for the AChE and for the nsChE. Maneb, ETU and zineb showed consistent decrease in the reactivity for the AChE (+ +) and for the nsChE (+ +). The decrease by DSF of the reactions for both the AChE (+) as well as for the nsChE(+) was even more pronounced indicating a possible nerve damage to the cholinergic innervation of rat intestine. Kinetic differences may explain the divergent effects between the agents studied.

Animals↗
PubMed1994

Analysis of dithiocarbamate fungicides. Second-derivative UV-spectroscopic determination of CS2, COS, and thiram (TMTD).

The application of second-derivative UV-spectroscopy offers a highly sensitive and selective method for the determination of CS2 and COS, as acid hydrolysis products of dithiocarbamate und thiuram disulphide fungicides, using a methanolic amine absorption reagent (ethylenediamine, piperidine). With standard concentrations of 0.08-1.1 microgram CS2/ml and 0.3 to 2.0 micrograms COS/ml, respectively, calibration curves with good correlation coefficients (r > 0.999) were obtained. In comparison to the official method of the Deutsche Forschungsgemeinschaft (DFG method S15) the proposed alternative is at least 100 times more sensitive to CS2. Using the second derivative method it is possible not only to clearly differentiate between CS2 and COS but also to quantify both gases without resorting to tedious background corrections as compared to the direct photometric methods. Additionally, second derivative spectroscopy allows the direct determination of thiram in the concentration range 1-10 micrograms/ml after its extraction with chloroform. For example, thiram in water (10 micrograms/l) and in thiram/talc standards (10 mg/g) were determined with good precision (+/- 2.0%).

Fungicides, Industrial↗
PubMed1975

Volatility of fungicidal mercury compounds on wheat seeds.

The volatility of two fungicidal seed dressings, Panogen 15 B liquid and Panogen PX powder, containing methyl mercuric dicyandiamide in equivalent amounts at the dosage used, was compared with that of triple distilled mercury. Tests were made in the absence and presence of cleaned Manitou wheat of 12.0% and 17.1% moisture content. The Panogen formulations were compared at the recommended and twice the recommended rate at different dosages, storage periods and storage temperatures. The Hg content of air samples was determined by the Corte-Monkman method, capable of determining 0.4 ng of Hg, which in a 1-L air sample is equivalent to 0.049 ppb (v/v). The volatility of the interstitial air expressed as mug of Hg vapor/m3 air depended on temperature, wheat moisture content and storage duration and ranged from 150 to 2,240 for metallic Hg, 21 to 350 for Panogen 15 B, and 31 to 380 for PX. In the absence of wheat the volatility of 15 B was greatest (395) at -17.5 degees C and least (75) at 4.5 degrees C, but increased rapidly thereafter with increased temperature. Volatility of metallic Hg after application to wheat of 12.0% and 17.1% moisture content was not significantly reduced after four days storage, but that of Panogen 15 B and PX was reduced considerably, particularly at the higher moisture level. Thus, volatility of mercurial seed dressings cannot be predicted from Hg content alone. Reduction of volatility through possible irreversible chemical bonding of Hg with seed components is suggested for more detailed investigation.

Air↗
PubMed2004

Sensitized photooxygenation of the fungicide furalaxyl.

BACKGROUND: The photolysis of pesticides is of high current interest since light is one of the most important abiotic factors which are responsible for the environmental fate of these substances and may induce their conversion into noxious products. The action of light can also be mediated by oxygen and synthetic or naturally occurring substances which act as sensitizers. Our objective in this study was to investigate the photochemical behaviour of the systemic fungicide furalaxyl in the presence of oxygen and various sensitizers, and to compare the toxicity of the main photoproduct(s) to that of the parent compound. Previous reports on the direct photolysis of the pesticide demonstrated a very slow degradation and the only identified photoproducts were N-2,6-xylyl-D,L-alaninare and 2,6-dimethylaniline. METHODS: Solutions of furalaxyl in CH3CN were photooxygenate using a 500W high-pressure mercury lamp (through a Pyrex glass filter, lambda>300 nm) or a 650W halogen lamp or sunlight and the proper sensitizer. When sunlight was used, aqueous solutions were employed. The photodegradation was checked by NMR and/or GC-MS. The photoproducts were spectroscopically evidenced and, when possible, isolated chromatographically. Acute toxicity tests were performed on the rotifer Brachionus calyciflorus, the crustacean cladoceran Daphnia magna and the anostracan Thamnocephalus platyurus, while chronic toxicity tests (sublethal endpoints) comprised a producer, the alga Pseudokirchneriella subcapitata and the crustacean Ceriodaphnia dubia, as a consumer. RESULTS AND DISCUSSION: In the presence of both oxygen and sensitizer, furalaxyl underwent rapid photochemical transformations mainly to N-disubstituted formamide, maleic anhydride and a 2(5H)-furanone derivative. The formation of these products was rationalized in terms of a furan endoperoxide intermediate derived from the reaction of furalaxyl with active dioxygenated species (singlet oxygen, superoxide anion or ground state oxygen). The 2(5H)-furanone exhibited a higher toxicity than the parent compound. CONCLUSION: This work reports the first data on the photosensitized oxygenation of furalaxyl with evidence of the high tendency of the pesticide to undergo photodegradation under these conditions leading, among other things, to a 2(5H)-furanone, which is more toxic than the starting furalaxyl towards aquatic organisms. RECOMMENDATIONS AND OUTLOOK: Investigation highlights that the photolytic fate of a pesticide, although quite stable to direct photoreaction due to its low absorption of solar radiation at ground level, can be significantly influenced in the environment by the presence of substances with energy or electron-transfer properties as natural dyes, e.g. chlorophyll, or synthetic pollutants, e.g. polycyclic aromatic hydrocarbons (PAH).

Animals↗
PubMed1997

Hepatotoxicity of diisopropyl ester of malonic acid and chloromalonic acids, disinfection by-products of the fungicide isoprothiolane.

The fungicide isoprothiolane (diisopropyl 1,3-dithiolane-2-ylidenemalonate) decomposes to the diisopropyl esters of malonic acid (DM), chloromalonic acid (DCM) and dichloromalonic acid (DDCM) upon aqueous chlorination. In this study, the cytotoxicity of these compounds was examined using rat hepatocytes cultured on Matrigel. DCM and DDCM caused hepatocellular death at concentrations > 0.5 mM, while DM had no effect on the cell viability even at the maximum concentration examined (4 mM). Significant lipid peroxidation, measured as 2-thiobarbituric acid reactive substances, was observed in both DCM- and DDCM-treated hepatocyte cultures, and was significantly enhanced by pretreatment with 0.1 mM bis(p-nitrophenyl)phosphate (BNPP), a carboxylesterase inhibitor. When both BNPP and SKF-525A, a cytochrome P450 inhibitor, were present in the medium, DCM-induced cytotoxicity and lipid peroxidation were significantly suppressed compared to cultures with BNPP-treatment alone. By contrast, the DDCM-induced cytotoxicity was not affected by the combined pretreatment of SKF-525A and BNPP. These results indicate that DCM is metabolically activated by cytochrome P450 in an ester form, while DDCM is activated by a mechanism other than one involving cytochrome P450. To further elucidate the cytochrome P450 isozyme involved in the metabolic activation of DCM, microsomal lipid peroxidation was studied in vitro using microsomes from rats treated with beta-naphthoflavone, musk xylene, phenobarbital, pyrazole, or dexamethasone. Among these preparations, the microsomes from dexamethasone-treated rats showed the most extensive lipid peroxidation in the presence of DCM, and the lipid peroxidation was enhanced by BNPP as observed in hepatocyte cultures. These findings suggest the possible involvement of cytochrome P450 3A in the metabolic activation of DCM.

Animals↗
PubMed1997

Biological monitoring of the fungicide epoxiconazol during application.

A method was developed for the biological monitoring of the fungicide epoxiconazol (Opus; BASF). Comparison of the urine levels of a hydroxylated metabolite after dermal application to the levels after oral intake revealed a dermal absorption of 1-2.5% of the dose. In a field study with 10 applicators a dermal exposure ranging between 60 and 10,000 microgram/person/day was determined from the urine levels of a hydroxylated metabolite; the contribution of the inhalation exposure was found to be negligible. From these data an incorporation of 1 to 100 microgram epoxiconazol/person/day could be derived. The measured exposure was compared to two commonly used exposure models. The model calculation resulted in a dermal exposure of 555 microgram/person/day (German BBA model) and 2115 microgram/person/day (British POEM), respectively, which is in accordance with the actually measured exposure.

Adult↗
PubMed2000

Captan fungicide exposures of strawberry harvesters using THPI as a urinary biomarker.

Clothing affords harvesters considerable protection against the elements and can retain substantial amounts of pesticide residue from treated crops. Normal work clothing of female harvesters was supplemented with rubber latex gloves and facial scarves to determine whether those measures reduced exposure. Captan fungicide exposures in female strawberry harvesters were assessed by determining urine clearance rates of tetrahydrophalimide (THPI). Clean rubber gloves were supplied to the 41 harvesters for the 3 days of the study period in October 1995. The workers were divided into two groups consisting of either bare-handed or gloved workers, and 24-h urine specimens were collected each day. Female harvesters who worked bare-handed cleared 5.3 microg captan equivalents as THPI with a range of 0.4 to 13.8 microg/person/day. Harvesters who worked wearing rubber latex gloves cleared only 2.0 microg captan equivalents with a range of 0.9 to 4.3 microg/person/day. In this case clean rubber latex gloves reduced absorbed dose by 38%, compared to the dose absorbed by bare-handed workers. These results additionally indicate that when a pesticide is avidly retained by rubber latex gloves and not readily absorbed dermally as captan, estimates of absorbed dose based on passive dosimetry data may be less reliable than exposure estimates derived from urine biomonitoring.

Administration, Cutaneous↗
PubMed2004

Elimination of ergoline alkaloids following treatment of Ipomoea asarifolia (Convolvulaceae) with fungicides.

Ergoline alkaloids are constituents of Clavicipitaceous fungi living on Poaceae plants. Ergoline alkaloids as well as volatile oil are also present in Ipomoea asarifolia Roem. & Schult (Convolvulaceae). Treatment of this plant with two fungicides (Folicur, Pronto Plus) eliminates the ergoline alkaloids but not the volatile oil. Elimination of ergoline alkaloids occurs concomitantly with loss of fungal hyphae associated with secretory glands on the upper leaf surface of the Ipomoea plant. Our observations suggest that accumulation of ergoline alkaloids in the Convolvulaceae may depend on the presence of a plant-associated fungus.

Ergolines↗
PubMed2006

Fluorescence enhancement of carbendazim fungicide in cucurbit[6]uril.

The potential increase in fluorescence of a benzimidazole-type fungicide (carbendazim) due to complexation with cucurbit[6]uril is reported. The fluorescence of the probe carbendazim in aqueous Na2SO4 solution (pH=7.61) at room temperature is found to increase by a maximum factor of approximately 10.0 and blue-shifted up to approximately 11+/-1 nm with the increase in cucurbit[6]uril concentration up to approximately 5 mM. This fluorescence enhancement is the result of formation of a 1:1 guest-host inclusion complex, in which the guest carbendazim is incorporated inside the hydrophobic cavity of the host curbit[6]uril through the amido-ester part. Such mode of inclusion is supported by NMR spectral measurements, in which upon encapsulation, the resonance of the methyl-protons of the amido-ester moiety is shifted significantly to upfield in the (1)H NMR spectrum. Also, to assess the formation of inclusion complex, solid samples prepared by co-evaporation have been studied, using differential scanning calorimetry (DSC). Measurement of the enhancement as a function of cucurbit[6]uril concentrations yielded a value of the equilibrium constant (Ka) of 271+/-10 M(-1) at 25 degrees C. From the temperature dependence of the equilibrium constants, DeltaH and DeltaS values have been negative in sign, indicating the dipole-dipole interactions and the steric factors associated with the formation of this inclusion complex. It might be proposed that the spectral changes due to the inclusion of carbendazim are the result of decrease in the polarity of the surrounded media rather than the loss of carbendazim rotational mobility.

Benzimidazoles↗
PubMed1991

Effect of the fungicides tributyltin acetate and tributyltin chloride on multilamellar liposomes: fluorescence studies.

The influence of tri-n-butyltin acetate (TBTA) and tri-n-butyltin chloride (TBTC) on the physico-chemical state of charged and neutral phospholipids was investigated using multilamellar liposomes. The thermal dependence of steady state fluorescence polarization of DPH and its charged derivative TMA-DPH was recorded. The two fungicides lowered DPPC phase transition temperature and broadened the temperature range of the transition in different ways. The effects were concentration-dependent. The results show that TBTC interacts more effectively with DPPC model membranes rather than TBTA. Moreover, TBTC broadens and shifts the main phase transition (Tm) more effectively in DPPC rather than in DMPC liposomes. Below Tm, TBTC decreases fluorescence polarization (P) in all phospholipids used. Above Tm P is almost constant in phospholipids with saturated acyl chains, except for DMPG. In fact, an increase of P is detectable in this lipid as in PLs with unsaturated acyl chains. It is suggested that the effects of TBT on liposomal membranes are dependent on the anion moiety and phospholipids characteristics.

1,2-Dipalmitoylphosphatidylcholine↗