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1.
The degradation of bis(tri[1-14C]butyltin) oxide in two soils (1 mg tin kg?1) has been studied under laboratory conditions. Half of the applied compound disappeared from unsterilised silt loam and sandy loam in approximately 15 and 20 weeks, respectively; it disappeared also from the sterilised soils but to a lesser extent. The formation of small amounts of dibutyltin derivatives was established by thin-layer chromatography both in the unsterilised and sterile soils. The amount of unextractable radioactivity increased with time in the unsterilised and sterile soils. In the unsterilised soils 14C was released as [14C]carbon dioxide in amounts equivalent to 20% of the applied radioactivity for silt loam and 10.7% for sandy loam over a period of 42 weeks. Almost no [14C]carbon dioxide was released from the sterile soils, confirming microbial participation in the degradation of the compound in the unsterilised soils.  相似文献   

2.
A simple and rapid method for extracting benomyl residues from soils was compared with previous methods. Soil was extracted by shaking for 2 h at room temperature with (1:1) acetone/M aqueous ammonium chloride followed by clean-up by solvent partition and ultraviolet absorption estimation of carbendazim. Recoveries were comparable to those obtained by refluxing with methanolic hydrochloric acid for 4 h, hitherto the most efficient method reported, and were much greater than those obtained by extraction with ethyl acetate or chloroform. The new method gave more tractable extracts than those obtained by refluxing with methanolic hydrochloric acid, which form troublesome metal hydroxide precipitates during clean-up. In field experiments with 2-[14C]-benomyl and 2-[14C]-carbendazim, no radioactivity was found more than 25 mm from the soil surface during 10 months after surface application of 1 kg/ha. Carbendazim residues in soils from three field experiments indicated that its persistence is very sensitive to soil pH. The time for 50% loss of initial dose ranged from 26 months at pH 5.5 to less than 3 months at pH 7.2. Biological effectiveness in a crop may therefore depend markedly on differences in soil pH.  相似文献   

3.
Ring- and carboxyl-labelled [14C]2,4-D were incubated under laboratory conditions, at the 2 g/g level, in a heavy clay, sandy loam, and clay loam at 85% of field capacity and 20 1C. The soils were extracted at regular intervals for 35 days with aqaeous acidic acetonitrile, and analysed for [14C]2,4-D and possible radioactive degradation products. Following solvent extraction, a portion of the soil residues were combusted in oxygen to determine unextracted radioactivity as [14C]carbon dioxide. The remaining soil residues were then treated with aqueous sodium hydroxide, and the radioactivity associated with the fulvic and humic soil components determined. In all soils there was a rapid decrease in the amounts of extractable radioacitivity, with only 5% of that applied being recoverable after 35 days. All recoverable radioactivity was attributable to [14C]2,4-D, and no [14C]-containing degradation products were observed. This loss of extractable radioactivity was accompanied by an increase in non-extractable radioactivity. Approximately 15% of the applied radioactivity, derived from carboxyl-labelled [14C]2,4-D, and 30% from the ring-labelled [14C]2,4-D was associated with the soil in a non-extractable form, after 35 days of incubation. After 35 days, less than 5% of the radioactivity from the carboxyl-labelled herbicide, and less than 10% of the ringlabelled material, was associated with the fulvic components derived from the three soils. Less than 5% of the applied radioactivities were identifiable with any of the humic acid components. It was considered that during the incubation [14C]2,4-D did not become bound or conjugated to soil components, and that non-extractable radioactivity associated with the three soil types resulted from incorporation of radioactive degradation products, such as [14C]carbon dioxide, into soil organic matter.  相似文献   

4.
The dependence of the behaviour of metsulfuron-methyl on soil pH was confirmed during incubations under controlled laboratory conditions with two French soils used for wheat cropping. The fate of [14C] residues from [triazine-14C]metsulfuron-methyl was studied by combining different experimen-tal conditions: soil pH (8·1 and 5·2), temperature (28 and 10°C), soil moisture (90 and 50% of soil water holding capacity) and microbial activity (sterile and non-sterile conditions). Metsulfuron-methyl degradation was mainly influenced by soil pH and temperature. The metsulfuron-methyl half-life varied from five days in the acidic soil to 69 days in the alkaline soil. Under sterile conditions, the half-life increased in alkaline soil to 139 days but was not changed in the acidic soil. Metsulfuron-methyl degradation mainly resulted in the formation of the amino-triazine. In the acidic soil, degradation was characterised by rapid hydrolysis giving two specific unidentified metabolites, not detected during incubations in the alkaline soil. Bound residues formation and metsulfuron-methyl mineralisation were highly correlated. The extent of bound residue formation increased when soil water content decreased and was maximal [48 (±4)% of the applied metsulfuron-methyl after 98 incubation days] in the acidic soil at 50% of the water holding capacity and 28°C. Otherwise, bound residues represented between 13 and 32% of the initial radioactivity. © 1998 SCI  相似文献   

5.
A laboratory study was conducted to determine the degradation rates and identify major metabolites of the herbicide metsulfuron-methyl in sterile and non-sterile aerobic soils in the dark at 20°C. Both [phenyl-U-14C]- and [triazine-2-14C]metsulfuron-methyl were used. The soil was treated with [14C]metsulfuron-methyl (0.1 mg kg−1) and incubated in flow-through systems for one year. The degradation rate constants, DT50, and DT90 were obtained based on the first-order and biphasic models. The DT50 (time required for 50% of applied chemical to degrade) for metsulfuron-methyl, estimated using a biphasic model, was approximately 10 days (9–11 days, 95% confidence limits) in the non-sterile soil and 20 days (12–32 days, 95% confidence limits) in the sterile soil. One-year cumulative carbon dioxide accounted for approximately 48% and 23% of the applied radioactivity in the [phenyl-U-14C] and [triazine-2-14C]metsulfuron-methyl systems, respectively. Seven metabolites were identified by HPLC or LC/MS with synthetic standards. The degradation pathways included O-demethylation, cleavage of the sulfonylurea bridge, and triazine ring opening. The triazine ring-opened products were methyl 2-[[[[[[[(acetylamino)carbohyl]amino]carbonyl]amino] carbonyl]-amino]sulfonyl]benzoate in the sterile soil and methyl 2-[[[[[amino[(aminocarbonyl)imino]methyl] amino]carbonyl]amino]sulfonyl]benzoate in the non-sterile soil, indicating that different pathways were operable. © 1999 Society of Chemical Industry  相似文献   

6.
Soils which have been pretreated with carbofuran can degrade the insecticide more rapidly than untreated soils, with a consequent loss of efficacy. In laboratory studies, soils pretreated with carbofuran were found to degrade the chemical more rapidly than soils which were not so pretreated. When pretreated soils were sterilised, the rate of carbofuran degradation was much reduced, indicating that most of it was due to microbial action. Incubation of pretreated soil with [phenyl-U-14C]carbofuran led to the rapid disappearance of the parent compound (3 % left after seven days). Most of the 14C was accounted for as bound residue after seven days, whilst smaller amounts were recovered as carbon dioxide, 3-hydroxycarbofuran, 3-ketocarbofuran, and an unknown metabolite. Incubation of pretreated soil with [carbonyl-14C]carbofuran led to rapid loss of the parent compound and the recovery of 73% of 14C as carbon dioxide by five days. Most of the bound 14C (>90%) arising from [phenyl-U-14C]carbofuran treatment of pretreated soil was extracted by 1 M sodium hydroxide and about half of the extracted 14C was precipitated with ‘humic acids’ after acidification. These and other results suggest that the major metabolic route for carbofuran in pretreated soils involves hydrolysis of the ester bond leading to (1) release of carbofuran phenol which rapidly binds to soil organic matter and, (2) release of the carbonyl moiety which quickly degrades to generate carbon dioxide.  相似文献   

7.
The biomineralization of [14C]glyphosate, both in the free state and as 14C-residues associated with soybean cell-wall material, was studied in soil samples from four different agricultural farming systems. After 26 days, [14C]carbon dioxide production from free glyphosate accounted for 34–51% of the applied radiocarbon, and 45–55% was recovered from plant-associated residues. For three soils, the cumulative [14C]carbon dioxide production from free glyphosate was positively correlated with soil microbial biomass, determined by substrate-induced heat output measurement and by total adenylate content. The fourth soil, originating from a former hop plantation, and containing high concentrations of copper from long-term fungicide applications, did not fit this correlation but showed a significantly higher [14C]carbon dioxide production per unit of microbial biomass. Although the cumulative [14C]carbon dioxide production from plant-associated 14C-residues after 26 days was as high as from the free compound, it was not correlated with the soil microbial biomass. This indicates that the biodegradation of plant-associated herbicide residues, in contrast to that of the free compound, involves different degradation processes. These encompass either additional steps to degrade the plant matrix, presumably performed by different soil organisms, or fewer degradation steps since the plant-associated herbicide residues are likely to consist mainly of easily degradable metabolites. Moreover, the bioavailability of plant-associated pesticide residues seems to be dominated by the type and strength of their fixation in the plant matrix. ©1997 SCI  相似文献   

8.
Accelerated degradation of vernolate, EPTC and butylate but not of cycloate was detected in soils from three locations in Israel which were treated annually with vernolate. Repeated application of EPTC to soils with and without a history of vernolate application, under laboratory conditions, resulted in a progressive increase in its rate of dissipation with each application. Accelerated degradation of EPTC was also rapidly induced by mixing small amounts (5%) of soil with a history of vernolate treatment with soil that had never received vernolate. Liberation of 14CO2 from [14C]EPTC was more rapid in vernolate-treated soils than in untreated soils, indicating a development of microbial populations in soil capable of rapidly degrading the EPTC. Degradation of [14C]EPTC was faster in soil previously cropped with maize than in non-cropped soil, but slower in soils cropped with cotton or peanuts.  相似文献   

9.
Aqueous suspensions and oil emulsions of a commercial [14C]diflubenzuron (N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide) formulation (Dimilin W-25) remained on the leaf surface of greenhouse-treated plant tissues. Absorption, translocation, and metabolism of the [14C]diflubenzuron were not significant. Less than 0.05% of the applied 14C was found in newly developed plant tissues 28 days after spray treatment. [14C]Diflubenzuron was degraded in soil. After 91 days, biometer flask studies showed that 28% of the 14C incorporated into the soil as [14C]diflubenzuron was recovered as 14CO2. Major dichloromethane-soluble soil residues were identified as unreacted [14C]diflubenzuron and [14C]4-chlorophenylurea. A minor unknown degradation product cochromatographed with 2,6-difluorobenzoic acid. Insoluble 14C-residues increased with time and represented 67.8% of the residual 14C in the soil 89 days after treatment. Cotton plants grown for 89 days in [14C]diflubenzuron-treated soil contained only 3% of the 14C applied to the soil. Small quantities of acetonitrile-soluble [14C]4-chlorophenylurea were isolated from the foliar tissues. Root tissues contained small amounts of [14C]diflubenzuron and trace quantities of a minor 14C-product that chromotographed similarly to 2,6-difluorobenzoic acid. Most of the 14C in the plant tissues (84–93%) was associated with an insoluble residue fraction 89 days after treatment.  相似文献   

10.
The experimental, aquatic herbicide fluridone (1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)-pyridinone) was degraded in two submersed soils and in the water above those soils to one acidic metabolite (identified as 1,4-dihydro-1-methyl-4-oxo-5-[3-(trifluoromethyl)phenyl]-3-pyridinecarboxylic acid by mass spectrometry). A sandy and a silt loam soil were treated with [14C]fluridone, immersed in water, and analyzed after 1, 3, 5, 7, 9, and 12 months. Seven to fifteen percent of the 14C applied to the soils was recovered in the water on each of the various collection dates. The acidic metabolite accounted for 86 to 93% of the radioactivity in the water fraction 7 months after treatment. The metabolite was absorbed strongly by both soils and comprised about 60% of the total 14C in each soil after 12 months. The remainder of the 14C in the soils after 12 months was either the parent compound (~30%) or an undefined insoluble residue (~10%).  相似文献   

11.
Chlorpyrifos [O,O-diethyl O-(3,5,6-trichloro-2-pyridyl) phosphorothioate] is an organophosphorus insecticide applied to soil to control pests both in agricultural and in urban developments. Typical agricultural soil applications (0.56 to 5.6 kg ha?1) result in initial soil surface residues of 0.3 to 32 μg g?1. In contrast, termiticidal soil barrier treatments, a common urban use pattern, often result in initial soil residues of 1000 μg g?1 or greater. The purpose of the present investigation was to understand better the degradation of chlorpyrifos in soil at termiticidal application rates and factors affecting its behaviour. Therefore, studies with [14C]chlorpyrifos were conducted under a variety of conditions in the laboratory. Initially, the degradation of chlorpyrifos at 1000 μg g?1 initial concentration was examined in five different soils from termite-infested regions (Arizona, Florida, Hawaii, Texas) under standard conditions (25°C, field moisture capacity, darkness). Degradation half-lives in these soils ranged from 175 to 1576 days. The major metabolite formed in chlorpyrifos-treated soils was 3,5,6-trichloro-2-pyrid-inol, which represented up to 61% of applied radiocarbon after 13 months of incubation. Minor quantities of [14C]carbon dioxide (< 5%) and soil-bound residues (? 12%) were also present at that time. Subsequently, a factorial experiment examining chlorpyrifos degradation as affected by initial concentration (10, 100, 1000 μg g?1), soil moisture (field moisture capacity, 1.5 MPa, air dry), and temperature 15, 25, 35°C) was conducted in the two soils which had displayed the most (Texas) and least (Florida) rapid rates of degradation. Chlorpyrifos degradation was significantly retarded at the 1000 μg g?1 rate as compared to the 10 μg g?1 rate. Temperature also had a dramatic effect on degradation rate, which approximately doubled with each 10°C increase in temperature. Results suggest that the extended (3–24 + years) termiticidal efficacy of chlorpyrifos observed in the field may be due both to the high initial concentrations employed (termite LC 50 = 0.2– 2 μg g?1) and the extended persistence which results from employment of these rates. The study also highlights the importance of investigating the behaviour of a pesticide under the diversity of agricultural and urban use scenarios in which it is employed.  相似文献   

12.
[14C]Diflubenzuron is readily degraded in various agricultural soils and in hydro-soil; 50% of the applied dose of 1 mg kg−1 was metabolised in 2 days or less. The chief products of hydrolysis were identified as 4-chlorophenylurea and 2, 6-difluorobenzoic acid. A part of the radioactivity, increasing with incubation time, could not be extracted. Release from the soil of [14C]carbon dioxide, derived from both labelled phenyl rings, points to the ultimate mineralisation of diflubenzuron.  相似文献   

13.
Ammonium sulphate and urea, but not potassium sulphate, increased the persistence of carbaryl in a flooded laterite soil with a low native nitrogen content (0.04%), but not in an alluvial soil with a higher nitrogen content (0.11%). Thus, NH4+ but not SO42-, contributed to the increased persistence of carbaryl. Likewise, ammonium sulphate increased the persistence of carbofuran in the laterite soil, but not in the alluvial soil. Significant accumulations of 1-naphthol and 2,3-dihydro-2, 2-dimethylbenzofuran-7-ol (‘carbofuran phenol’), in soils treated with carbaryl or carbofuran, suggested hydrolysis as the major pathway of degradation. Treatment of the two soils with ammonium sulphate, urea or potassium sulphate led to a decrease in soil-bound residues and an increase in the respective hydrolysis products, compared with untreated soils. Sorption studies indicated that NH4+ and SO42- compete with carbaryl, 1-naphthol and carbofuran for sorption and exchange sites in the complex soil system. Evolution of [14C]carbon dioxide from ring-14C in carbaryl and carbofuran was negligible. Consequently, after 40 days, more than 50% of the 14C in [14C]carbaryl and [14C]carbofuran remained in the soils as hydrolysis products (1-naphthol or 2,3-dihydro-2,2-dimethylbenzofuran-7-ol) plus soil-bound residues.  相似文献   

14.
The potential to mineralize 2,4‐dichlorophenoxyacetic acid (2,4‐D), mecoprop, isoproturon and terbuthylazine was studied in soil and aquifer chalk sampled at an agricultural field near Aalborg, Denmark. Laboratory microcosms were incubated for 258 days under aerobic conditions at 10 °C with soil and chalk from 0.15–4.45 m below the surface. The [ring‐U14C]‐labeled herbicides were added to obtain a concentration of 6 µg kg?1 and mineralization was measured as evolved [14C]carbon dioxide. The herbicides were readily mineralized in soil from the plough layer, except for terbuthylazine, which was mineralized only to a limited extent. In the chalk, lag periods of at least 40 days were observed, and a maximum of 51%, 33% and 6% of the added 2,4‐D, mecoprop and isoproturon, respectively, were recovered as [14C]carbon dioxide. Large variations in both rate and extent of mineralization were observed within replicates in chalk. No mineralization of terbuthylazine in chalk was observed. As a measure of the general metabolic activity towards aromatic compounds, [ring‐U14C]‐benzoic acid was included. It was readily mineralized at all depths. © 2000 Society of Chemical Industry  相似文献   

15.
The degradation of the wild-oat herbicide flamprop-isopropyl, [isopropyl (±)-N-benzoyl-N-(3-chloro-4-fluorophenyl)alaninate], in four soils has been examined under laboratory conditions with sampling times of up to 45 weeks after treatment. The major degradation product of [14C]flamprop-isopropyl in all soils at up to 10 weeks after treatment was the carboxylic acid (±)-N-benzoyl-N-(3-chloro-4-fluorophenyl)alanine. This compound in turn underwent degradation by loss of the benzoyl group and the propionic acid moiety, with evolution of [14C]carbon dioxide to form 3-chloro-4-fluoroaniline (CFA). The CFA was formed slowly in soil and occurred mainly as a bound form. There was evidence to show that the CFA was subsequently converted into other polar products. The time for depletion of 50% of the applied herbicide was approximately 10 weeks in sandy loam and medium loam soils, 11 weeks in a clay loam soil and 23 weeks in a peat soil.  相似文献   

16.
The relative persistence of [14C]-gamma-BHC and [14C]-beta-BHC in Indian rice soils under flooded conditions was studied. In alluvial, laterite and pokkali (acid sulphate, saline) soils, rapid degradation of both isomers occurred; in sandy and kari (acid sulphate, saline) soils, both isomers persisted even after 41 days of flooding. The rapid degradation of BHC isomers in the former three soils was related to highly negative redox potentials within 20 days of flooding in contrast to oxidised conditions in sandy and kari soils even after 41 days. During the degradation in the soils, beta-BHC showed longer lag than gamma-BHC. Results suggest that the degradation of beta-BHC commences at a potential lower than that required for gamma-BHC degradation. Greater decomposition of gamma-BHC occurred in rice straw-amended soils than in unamended soils when the insecticide was incorporated to the soils in an aqueous solution. Addition of BHC isomers to the soils in ethanol resulted in comparable rates of rapid decomposition in both rice straw-amended and unamended soils, since ethanol was as effective as rice straw in lowering the redox potentials of the soils favouring BHC decomposition in unamended soil as well.  相似文献   

17.
The degradation of the wild oat herbicide flamprop-methyl [methyl DL -N-benzoyl-N-(3-chloro-4-fluorophenyl)alaninate] in four soils has been studied under laboratory conditions using 14C-1abelled samples. The flamprop-methyl underwent degradation more rapidly than its analogue flamprop-isopropyl. However, similar degradation products were formed, namely the corresponding carboxylic acid and 3-chloro-4-fluoroaniline. The latter compound occurred mainly as ‘bound’ forms although evidence was obtained of limited ring-opening to give [14C]carbon dioxide. The time for depletion of 50% of the applied herbicide was approximately 1-2 weeks in sandy loam, clay and medium loam soils and 2-3 weeks in a peat soil.  相似文献   

18.
A. HELWEG 《Weed Research》1987,27(4):287-296
MCPA was weakly absorbed in soils with 2.4, 3.0 and 2.9% humus. Kd-values were 0.7, 0.9 and 1.0, respectively. In soil, not previously treated with MCPA, the degradation of 0.05 mg kg?114C-MCPA followed first-order reaction kinetics whereas degradation of 5 mg kg?1 was only first-order for 2 weeks; exponentially increasing degradation rates followed indicating enrichment of the soil with MCPA decomposers. Degradation was monitored by evolution of 14CO2. The influence of temperature on degradation of MCPA (4 mg kg?1) could initially be described by Q10 values or by the Arrhenius equation. After 1 day of incubation in two field soils Q10 values were 3.3 and 2.9, respectively, between 0°C and 29°C; the activation energies were 87 and 76 kj mol?1. Exponentially increasing degradation rates followed with doubling times of about 4.0, 1.8, 1.2 and 0.6 days at 6,10, 15 and 21°C, respectively. After 51 days of incubation, at temperatures between 6°C and 29°C, about 60%14C was evolved in CO2 and only traces of MCPA were left in the soil. At 0°C and at 40°C only 1% and 10%14C, respectively, were evolved as CO2 after 51 days. 14C-MCPA (4 mg kg?1) was incubated at moisture contents from that in air-dried soil to 2.3 times field capacity. Optimum for degradation was from 0.6 to 1.2. field capacity. Degradation was very slow where water contents were below the level of wilting point and was nil in air-dried soil. In wet soil degradation was delayed, but even in water-logged soil (2.3 times field capacity) MCPA was decomposed after 4 to 5 weeks at 10°C.  相似文献   

19.
The persistence of bromoxynil (3,5-dibromo-4-hydroxybenzonitrile), [14C]dicamba (3,6-dichloro-2-methoxybenzoic-7-14C acid) and propanil [N-(3,4-dichlorophenyl)propionamide] at rates equivalent to 1 kg ha?1, were studied under laboratory conditions in a clay loam, a heavy clay and a sandy loam at 85% of field capacity and at 20±1°C, both singly and in the presence of herbicides normally applied with these chemicals as tank-mix or split-mix components. The degradation of bromoxynil was rapid with over 90% breakdown occurring within a week in the heavy clay and sandy-loam soils, while in the clay-loam approximately 80% of the bromoxynil had broken down after 7 days. In all three soils degradation was unaffected by the presence of asulam, diclofop-methyl, flamprop-methyl, MCPA, metribuzin or propanil. Propanil underwent rapid degradation in all soil treatments, with over 95% of the applied propanil being dissipated within 7 days. There were no noticeable effects on propanil degradation resulting from applications of asulam, barban, bromoxynil, dicamba, MCPA, MCPB, metribuzin or 2,4-D. The breakdown of [14C]dicamba in a particular soil was unaffected by being applied alone or in the presence of diclofop-methyl, flampropmethyl, MCPA, metribuzin, propanil or 2,4-D. The times for 50% of the applied dicamba to be degraded were approximately 16 days in both the clay loam and sandy loam, and about 50 days in the heavy clay.  相似文献   

20.
The persistence of [14C]MCPA at a rate equivalent to 1 kg ha?1 was studied under laboratory conditions in a clay loam, heavy clay and sandy loam at 85% of field capacity moisture and 20±1°C both alone and in the presence of tri-allate, trifluralin, tri-allate and trifluralin, malathion, Vitaflow DB, malathion and Vitaflow DB, bromoxynil, bromoxynil and asulam, bromoxynil and difenzoquat, dicamba, dicamba and mecoprop, linuron, MCPB, metribuzin, propanil, TCA, benzoylprop-ethyl, diclofop-methyl, and flamprop-methyl. Except in the soils treated with asulam, the half-lives of [14C]MCPA in all three soil types were similar, being approximately 13±1 days, thus indicating that none of the other chemicals studied adversely affected the soil degradation of MCPA. In the asulam treated soils, the half-lives of the MCPA were about 3 days longer than in non-asulam treated soils; the effect was most marked in the clay loam.  相似文献   

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