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1.
Goldfish (Carassius auratus) exposed to 20 parts per billion [14C]photodieldrin in a static system absorbed 80% of the radioactivity within 20 hr. The absorbed radioactivity was eliminated slowly with a half-life of 3 weeks. Photodieldrin and a ketone derivative were the major form of the radiocarbon eliminated in water, accounting for, respectively, 59 and 10.4% of the eliminated radioactivity. The ketone derivative was characterized by cochromatography (thin-layer and gas chromatography, gc) and gc-mass spectrometry. Approximately, 15 other polar and nonpolar metabolites were detected in the aqueous medium. The radioactivity in the fish consisted of 13 metabolites along with photodieldrin. Photodieldrin and the ketone derivative were the most abundant residues in the fish, accounting for 77 and 5.4% of the radioactivity, respectively.  相似文献   

2.
The exposure of bluegill fish to 50 parts per billion [14C]dieldrin in a static system resulted in the absorption of 73.00% of the radioactivity in 48 hr. Following transfer of the fish to clean water, only 16.20% of the absorbed radiolabel was eliminated in 23 days. Out of the 93.65% of the absorbed radioactivity recovered, 9 radioactive spots were isolated which included unchanged dieldrin (74.39%), pentachloroketone (8.17%), and aldrin-trans-diol (8.04%) as major metabolites.  相似文献   

3.
Bluegill fish, following exposure to [14C]photodieldrin eliminated 50% of the absorbed radioactivity in 3 weeks. Analysis of the products revealed that about 27% of the eliminated radioactivity was due to the unaltered photodieldrin while the rest consisted of at least 11 metabolites in free and conjugated forms. Photodieldrin ketone was the major excretory product. Solvent extracts of the whole fish examined showed 4 metabolites in addition to about 90% of the unmetabolized photodieldrin. The ketone derivative was the most predominant of the metabolic products.  相似文献   

4.
Orally administered [1-14C]ethyl paraoxon, O,O-diethyl-O-p-nitrophenyl phosphate, is readily absorbed from the gastrointestinal tract of male albino rats. Radioactivity is essentially eliminated in 72 hr by excretion into urine and feces and by expiration as 14CO2. Compounds with radioactivity in the urine are tentatively identified as diethyl phosphoric acid, desethyl paraoxon, ethanol, metabolites conjugated with amino acids, and paraoxon; the first compound is the predominant radioactive metabolite. Intraperitoneally injected phenobarbital, DDT, dieldrin, and endrin are inducers of microsomal enzymes that degrade paraoxon. The aryl phosphate-cleaving activity in vitro is not dependent on the addition of NADPH. O-Dealkylation of paraoxon is catalyzed by microsomal enzymes that require NADPH and oxygen and are inhibited by carbon monoxide. Microsomal enzymes from rats pretreated with enzyme inducers give an increased rate of O-dealkylation of paraoxon. Reduced glutathione has little or no effect on paraoxon degradation by either microsomal or soluble enzymes. Actinomycin D inhibits O-dealkylation of paraoxon in vivo, as indicated by reduction of 14CO2 formation, and in vitro, as indicated by decreased activity of microsomal O-dealkylase. The role of microsomal mixed-function oxidases and NADPH-dependent O-dealkylase in the metabolism of organophosphorus insecticides is discussed.  相似文献   

5.
The accumulation, persistence, and metabolism and/or elimination of methoprene (isopropyl (2E, 4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate) was examined for bluegill sunfish (Lepomis macrochirus) contained in a dynamic flow-through system and a model aquatic ecosystem. The fish in the dynamic flow-through system acquired moderate residues of largely unmetabolized methoprene when continuously exposed to about 30 times anticipated environmental levels of methoprene, but residues were rapidly eliminated (93–95%) within 2 weeks when fish were transferred to flowing uncontaminated water. When bluegill were treated with methoprene in a model aquatic ecosystem, fish showed a highly misleading accumulation of 14C residues since residual radioactivity was found almost exclusively in radiolabeled natural products, including cholesterol, free fatty acids, glycerides, and protein. Less than 0.1% of the total radioactivity in fish could be attributed to unmetabolized methoprene or its primary metabolites; thus, simple radioassay procedures in ecosystem studies can be severely compromised unless coupled with more sophisticated analytical techniques.  相似文献   

6.
Metribuzin [4-amino-6-tert-butyl-3(methylthio)-1,2,4-triazin-5(4H)-one] metabolism was studied in soybean [Glycine max (L.) Merr. Tracy]. Pulse treatment studies with seedlings and excised mature leaves showed that [5-14C]metribuzin was absorbed rapidly and translocated acropetally. In seedlings, >97% of the root-absorbed 14C was present in foliar tissues after 24 hr. In excised leaves, 50–60% of the absorbed 14C remained as metribuzin 48 hr after pulse treatment, 12–20% was present as polar metabolites, and 20–30% was present as an insoluble residue. Metabolites were isolated by solvent partitioning, and were purified by adsorption, ion-exchange, thin-layer, and high-performance liquid chromatography. The major metabolite (I) was identified as a homoglutathione conjugate, 4-amino-6-tert-butyl-3-S-(γ-glutamyl-cysteinyl-β-alanine)-1,2,4-triazin-5(4H)-one. Metabolite identification was confirmed by qualitative analysis of amino acid hydrolysis products, fast atom bombardment (FAB), and chemical ionization (CI) mass spectrometry, and by comparison with a reference glutathione conjugate synthesized in vitro with a hepatic microsomal oxidase system from rat. Minor metabolites were identified as an intermediate N-glucoside conjugate (II), a malonyl N-glucoside conjugate (III), and 4-malonylamido-6-tert-butyl-1,2,4-triazin-3,5(2H,4H)-dione (N-malonyl DK, IV) by CI and FAB mass spectrometry. Alternative pathways of metribuzin metabolism are proposed.  相似文献   

7.
The phytotoxicity of 2,4-bis(isopropyl)-6-(methylthio)-s-triazine (prometryne) and 2-(tert-butylamino)-4-(ethylamino)-6-(methylthio)-s-triazine (terbutryn) to peas (Pisum sativum L. var. Perfection 3040) was studied. No differences were found when the herbicides were applied to the roots of intact plants in nutrient solution or directly to leaf discs. However, prometryne was much more toxic when uptake was from soil. Absorption and translocation of 14C-labeled prometryne and terbutryn showed that the majority of terbutryn accumulated in the roots, whereas prometryne was uniformly distributed between the roots and the shoot. Thin layer chromatography of extracts from prometryne-treated peas showed that only 20% of the absorbed compound was metabolized to produce one breakdown product. Extracts of terbutryn-treated plants contained three different metabolites. After 120 hr of exposure to terbutryn, about half of the absorbed herbicide was metabolized. The results show that the main factors responsible for the differential toxicity of the herbicides to peas were availability from the soil, translocation pattern and initial detoxication.  相似文献   

8.
[14C]Endrin was fed to two lactating cows in a portion of their diet for 21 days. The intake was equivalent to approximately 0.1 mg of endrin per kg of total diet. Excretion of radioactivity in milk, urine and faeces reached equilibrium with intake between 4 and 9 days after starting treatment. Milk residues reached 0.003–0.006 mg/kg, were composed of unchanged endrin and were located in the fat. Muscle residues reached 0.001–0.002 mg/kg. Residues in the fat reached a maximum of 0.1 mg/kg and were due to unchanged endrin. [14C]Endrin was administered in corn oil to six laying hens for 21 weeks. The intake was equivalent to approximately 0.13 mg/kg of total diet. Ingestion and excretion were almost in balance at 16–20 weeks. Egg residues reached 0.11–0.18 mg/kg, were composed of unchanged endrin and were located in the yolk. Tissue residues were 0.01 mg/kg in breast, 0.1 mg/kg in leg, 0.17 mg/kg in kidney, 0.47 mg/kg in liver and 1.0 mg/kg in fat. The residues were accounted for as unchanged endrin except in liver and kidney in which part was probably due to polar metabolites in the process of excretion. The results show that endrin is much more rapidly metabolised in cows than in hens. The pathways of metabolism were fundamentally the same in both species, the major product being anti-12-hydroxyendrin, which was found un-conjugated in cow urine and faeces and as the O-sulphate conjugate in hen excreta. The only observed difference in primary metabolism was some syfl-12-hydroxyendrin and 12-ketoendrin in cows. This pathway was not detected in hens.  相似文献   

9.
The short-term disposition and metabolism of topically administered [14C]chlorpyrifos was assessed in the black imported fire ant (Solenopsis richteri Forel) in the presence and absence of the mixed-function oxidase inhibitor piperonyl butoxide. Chlorpyrifos is readily absorbed into an internal organosoluble fraction which was quickly converted into a water-soluble fraction. The radioactivity was slowly excreted over a 24-hr period. Piperonyl butoxide slowed the conversion of the internal organosoluble radioactivity to the water-soluble fraction. Thin-layer chromatography indicated that piperonyl butoxide slowed the conversion of chlorpyrifos to material remaining at the origin, presumably water-soluble metabolites. The results of acid hydrolysis studies indicated that the water-soluble radioactivity was comprised mainly of conjugates. Although very little chlorpyrifos oxon was recovered in the metabolism experiments, in vitro studies on fire and head homogenates showed the compound to be an extremely potent anticholinesterase, with an I50 of 4.6 × 10?10M, while a major metabolite, 3,5,6-trichloropyridinol, was an ineffective acetylcholinesterase inhibitor.  相似文献   

10.
Carbon-14 d-trans-phenothrin or 3-phenoxybenzyl d-trans-chrysanthemumate labeled at the hydroxymethyl group in the alcoholic moiety was administered orally to male Sprague-Dawley rats at the rate of 200 mg/kg. The compound was rapidly absorbed from the gastrointestinal tract and distributed into various tissues.Radioactivity was rapidly eliminated (over 3 days) via the urine (ca. 60%) and feces (ca. 40%). No detectable radioactive carbon dioxide was expired. The urinary and fecal metabolites were separated and identified, the predominant one being 3-(4′-hydroxy) phenoxybenzoic acid and amounting to approximately 55% of the recovered radioactivity. 3-Phenoxybenzoic acid, free and conjugated with glycine, was also identified. In vitro studies using liver preparation from rats, mice, guinea pigs, rabbits, and dogs revealed that d-trans-phenothrin was hydrolyzed to 3-phenoxybenzyl alcohol, which was subsequently oxidized. The l-trans isomer was also easily hydrolzyed, whereas d-cis- and l-cis-phenothrin were resistant to hydrolytic attack at the ester linkage.  相似文献   

11.
The excretion patterns and tissue residues were determined after single and repeated oral dosing of rats with triazophos-14C Within 4 days after a single oral dose 76.3 % of the 14C was excreted in the urine and 21.0% in the faeces. After daily application for 12 days 69.5–83.4% of the label was eliminated in urine and 30.9–18.1 % in the faeces. Following prolonged application, however, elimination is distinctly slower. Distribution of radioactive residues in organs and tissue in both test series showed no appreciable or critical concentrations of radioactivity, with the exception of the gastrointestinal tract (contents and walls). Unchanged triazophos and l-phenyl-1,2,4-triazol-3-ol-3-14C were excreted in the faeces. Renewed release of other metabolites into the gastrointestinal tract apparently does not take place. The following metabolites are detected in the urine: urea-14C (approx. 85% of the radioactivity excreted with the urine); and three compounds as conjugates with glucuronic acid, i.e. 1-phenyl-l,2,4-triazol-3-ol-3-14C (approx. 3%), l-phenylsemicarbazide-3-14C (approx. 5%), and semicarbazide-14C (approx. 5%). Two further metabolites, so far unidentified, occurred in small quantities.  相似文献   

12.
The effects of piperonyl butoxide on metabolism of 14C-labeled methoxychlor, aldrin, and trifluralin were investigated in green sunfish, Lepomis cyanellus. Piperonyl butoxide inhibited epoxidation of aldrin to dieldrin, O-dealkylation of methoxychlor, and N-dealkylation of trifluralin, resulting in higher levels of total radioactivity in animals exposed to the combination compared to those exposed to pesticide alone. Where piperonyl butoxide was present a greater proportion of the total radioactivity in the fish extract occurred as parent compound compared to metabolites than in fish exposed to pesticide alone. After 16 days of exposure piperonyl butoxide increased the proportion of parent compound eight times for methoxychlor, 17 times for aldrin, and 15 times for trifluralin.  相似文献   

13.
The fate of the di-n-butylaminosulfenyl moiety in 2,3-dihydro-2,2-dimethyl-7-benzofuranyl (di-n-butylaminosulfenyl)(methyl)carbamate (DBSC or Marshal) was studied in the cotton plant at 1, 3, 6, and 10 days following foliage treatment with [di-n-butylamino-14C]DBSC. Dibutylamine and two major radioactive metabolites were obtained following extraction of the plant tissue with a methanol-buffer containing N-ethylmaleimide (NEM), a sulfhydryl scavenger which was added to prevent the cleavage of the NS bond during the workup procedure. The most adundant radioactive material recovered from plants was identified as a product arising from the reaction between NEM and dibutylamine. Extraction of plant tissue with straight methanol-buffer solution or with methol-buffer containing other sulfhydryl scavengers resulted in 57–86% of the applied radioactivity being recovered as dibutylamine in the organosoluble fraction. When [14C]dibutylamine was applied to cotton leaves, most of the radioactivity, i.e., 96% of the total recovered radioactivity, was found in the organosoluble fraction as dibutylamine. Dibutylamine is the major metabolite of [di-n-butylamino-14C]DBSC in the cotton plant.  相似文献   

14.
Absorption, translocation and metabolism of [14C]3-isopropyl-2,1,3-benzothiadiazin-4-one-2,2-dioxide (bentazon) by several plant species were investigated to determine the mechanism of bentazon selectivity.Marked selective phytotoxicities were observed between resistant rice (Oryza sativa L.) and susceptible Cyperus serotinus Rottb. when treated with bentazon. Absorption and transolcation of bentazon did not differ greatly between highly resistant rice and susceptible C. serotinus. However, a marked difference in bentazon metabolism occurred between the two species. In rice about 80% of the absorbed bentazon was metabolized within 24 h, and after 7 days about 85% was converted to a major water-soluble metabolite and unchanged bentazon was only 5%. In C. serotinus 50–75% of the radioactivity was unchanged bentazon after 7 days.Large amounts of water-soluble metabolites were detected in root-treated resistant plants such as barnyardgrass (Echinochloa crus-galli Beauv.), soybean (Glycine max Merr.) and corn (Zea mays L.), but only small amounts were present in such susceptible plants as Sagittaria pygmaea Miq. and Eleocharis kuroguwai Ohwi. Therefore, the mechanism of bentazon selectivity appears to be a difference between resistant and susceptible species in their ability to metabolize and detoxify bentazon.The major metabolite in rice was identified as 6-(3-isopropyl-2,1,3-benzothiadiazin-4-one-2,2-dioxide)-O-β-glucopyranoside, determined by GC-MS, NMR, IR and gas chromatography after hydrolysis with sulfuric acid or β-glucosidase.  相似文献   

15.
Diflubenzuron was absorbed and metabolised relatively slowly by the two-spotted spider mite Tetrunychus urticae Koch. Diflubenzuron metabolites, tentatively identified by coincident chromatography with reference standards, included 4- chlorophenylurea, 2, 6-difluorobenzoic acid, 4-chloroformanilide, 2, 6-difluoro-benzamide, and two compounds monohydroxylated in the chloroaniline moiety. There was little absorption of diflubenzuron when applied topically to leaves of bean plants. However, there was translocation of radioactive material when diflubenzuron was injected into the stern. In this case, the radioactivity, which was confined largely to vascular tissue, apparently moved acropetally but exhibited very little or no basipetal movement. Bean plants metabolised injected diflubenzuron, and certain of the metabolites were similar to those isolated from mites.  相似文献   

16.
Metribuzin [4-amino-6-tert-butyl-3-(methylthio)-1,2,4-triazin-5(4H)-one] metabolism was studied in tomato (Lycopersicon esculentum Mill. “Sheyenne”). Pulse-treatment studies with seedlings and excised leaves showed that [5-14C]metribuzin was rapidly absorbed, translocated (acropetal), and metabolized to more polar products. Foliar tissues of 19-day-old seedlings metabolized 96% of the root-absorbed [14C]metribuzin in 120 hr. Excised mature leaves metabolized 85–90% of the petiole-absorbed [14C]metrubuzin in 48 hr. Polar metabolites were isolated by solvent partitioning, and purified by adsorption, thin-layer, and high-performance liquid chromatography. A minor intermediate metabolite (I) was identified as the polar β-d-(N-glucoside) conjugate of metribuzin. The biosynthesis of (I) was demonstrated with a partially purified UDP-glucose: metribuzin N-glucosyltransferase from tomato leaves. A possible correlation between foliar UDP-glucose: metribuzin N-glucosyltransferase activity levels and differences in the tolerance of selected tomato seedling cultivars to metribuzin was suggested. The major polar metabolite (II) was identified as the malonyl β-d-(N-glucoside) conjugate of metribuzin.  相似文献   

17.
The gastric absorption of [1-naphthyl-1-14C]N-methylcarbamate (radiolabeled carbaryl) administered intragastrically (7.5 μmoles/kg body wt) to fasted, anesthetized female rats was investigated by measurement of 14C absorption and by identification of the radiolabeled constituents in the portal blood. At 22 and 67 min after dosing, 52.6 ± 14.1% (n = 3) and 81.7 ± 15.7% (n = 3), respectively, of the 14C was absorbed from the stomachs (ligated pylori) of rats with intact portal circulation. In another experiment, 69.1 ± 25.9% (n = 3) of the 14C was absorbed from the rat stomachs (ligated pylorus and esophagus) during 66.0 ± 1.0 min of total portal blood collection (via an in vivo perfusion technique). The radiolabeled material in the collected portal blood accounted for 97.2 ± 1.9% (n = 3) of the 14C absorbed from rat stomachs. On the basis of thin-layer chromatography, gas chromatography, and infrared spectroscopy, 89.3% of the radiolabeled material in the collected portal blood was [1-naphthyl-1-14C]N-methylcarbamate.  相似文献   

18.
Upon intravenous application of dihydrochlordene dicarboxylic acid-14C to rats, the radioactivity is quickly excreted, and 44% of the excreted radioactivity consists of metabolites. Nine metabolites have been isolated from feces and urine extracts. Three metabolites could be identified by means of authentic samples by thin layer chromatography, gas chromatography, and mass spectrometry: two isomers of dechlorodihydrochlordene-dicarboxylic acid (metabolites I and II, total 22.5%) and dihydrochlordene-dicarboxylic acid-dimethyl-ester (metabolite III, 11.3%).  相似文献   

19.
A rat, given a single oral dose of [14C] cymoxanil, 1-(2-cyano-2-methoxyimino-[2-14C]-acetyl)-3-ethylurea, eliminated 91% of the radioactivity within 72 h. The urine contained 71%, the faeces 11%, and the expired air about 7% of the radiolabel; no 14C residue was found in the internal organs. Greater than 70% of the radioactivity in the urine was identified. The major metabolite was characterised as glycine, both free and conjugated, as hippuric acid and phenylaceturic acid [N-(phenylacetyl)-glycine], and probably in the form of polypeptides of low molecular weight. The other metabolites identified included 2-cyano-2-methoxyiminoacetic acid, 2-cyano-2-hydroxyiminoacetic acid and 1-ethylimidazolidine-2, 4, 5-trione. The minor metabolites included succinic acid and 2-oxoglutaric acid which indicated reincorporation of metabolic 14C. Cymoxanil, as such, was not detected in the urine.  相似文献   

20.
[14C]Buturon, a urea herbicide, was sprayed on soil and winter wheat as an aqueous formulation (2.98 kg/ha) under outdoor conditions. Three months after application, a total of 49.2% of the applied radiocarbon was recovered: 46.9% in the soil, 0.3% in the leaching water (depth > 50 cm), and 2.0% in the plants. Radioactive residues in the soil were distributed to a depth of 50 cm and decreased with increasing depth of the soil. An average of 47% of the radioactivity present in the soil could be extracted with cold chloroform; by this extraction method, the formation of artefacts was avoided. Between one and two thirds of the extracted radioactivity was unchanged buturon. In the soil extracts, the following eight conversion products were isolated and identified by combined gas chromatography/mass spectrometry: N-(p-chlorophenyl)-N-methyl-O-methyl carbamate; N-(p-chlorophenyl)-O-methyl carbamate; N-(p-chlorophenyl)-N′-methyl-N′-isobutenyl-urea; N-(p-chlorophenyl)-N′-methyl-urea, N-(p-chlorophenyl)-N′-methyl-N′-isobutenylol-urea; p-chloroaniline in “biologically bound” form; N-(p-chlorophenyl)-N′-methyl-N′-methoxyisobutenyl-urea; and N-(p-chlorophenyl)-N′-methyl-N′-ethoxyisobutenyl-urea. In the leaching water, which contained only 0.005–0.006 mg/liter of radioactive substances, the following three conversion products were isolated and identified by gas chromatography/mass spectrometry: p-chloroformanilide; N-(p-chlorophenyl)-N-methyl-O-methyl carbamate; and an N-hydroxyphenyl-N′-methyl-N′-isobutinyl-urea. The results are discussed in relation to the factors responsible for the formation of these products.  相似文献   

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