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1.
The metabolism of the insecticide SD 8280 [2-chloro-1-(2,4-dichlorophenyl)vinyl dimethyl phosphate] in rice plants has been examined. When rice seedlings were treated with [14C]-SD 8280 the major metabolite was 1-(2,4-dichlorophenyl)ethanol which was present mainly conjugated with plant carbohydrates. This compound was also the major metabolite present in grain and straw from rice treated with [14C]-SD 8280 and grown to maturity under paddy conditions both in the glasshouse and in an outdoor enclosure. Other metabolites detected in the mature plants included 2-chloro-1-(2,4-dichlorophenyl)vinyl methyl hydrogen phosphate and 2,4-dichloro-benzoic acid, both of which occurred in free and conjugated forms. Paddy water was sampled at intervals after the application of [14C]-SD 8280 and the total residue in the water fell from initial levels of 0.28–1.1 μg/ml (expressed as SD 8280 equivalent) immediately after treatment to <0.01 μg/ml after 2–3 weeks. The total residues in the soil from these experiments were low and did not exceed 0.20 mg/kg (SD 8280 equivalents) through the 0–15 cm profile.  相似文献   

2.
The response of plant cell membranes to vinyl organophosphorus insecticides was studied by determining the release of intracellular materials as a measure of membrane permeability and the uptake of [1-14C]-α-aminoisobutyric acid as a measure of active transport. A pretreatment with chlorfenvinphos (2-chloro-1-(2,4-dichlorophenyl)-vinyl diethyl phosphate) at 0.4 mM or higher concentrations increased the leakage of cell contents from the tissues of pea, corn, and beet, but two other vinyl organophosphorus insecticides, tetrachlorvinphos (2-chloro-1-(2,4,5-trichlorophenyl)-vinyl diethyl phosphate) and phosphamidon (2-chloro-2-diethyl carbamoyl-1-methyl vinyl dimethyl phosphate), had no effect. Simultaneous addition of phospholipids, β-sitosterol, or Ca2+ inhibited in varying degrees the chlorfenvinphos-induced permeability, suggesting that the leakage of cell contents might be due to alteration in membrane structure.Chlorfenvinphos or tetrachlorvinphos at 0.1 mM or higher concentrations inhibited the uptake of α-aminoisobutyric acid. The degree of inhibition varied with different plant species. The inhibition was competitive and was not prevented by phospholipids. However, Ca2+ and other divalent cations were stimulatory to the uptake of α-aminoisobutyric acid, either in the presence or absence of chlorfenvinphos. Chlorfenvinphos also inhibited plant growth in tobacco callus and pea stem assays.From the differences in effective concentration, structural requirement, and interaction with phospholipids, it is suggested that chlorfenvinphos affected the membrane permeability and active transport by different mechanisms. These effects probably underlie its inhibitory action on plant growth.  相似文献   

3.
[14C]-Labelled methazole was incubated in six soils at 25°C and with soil moisture at field capacity. Under these conditions, methazole was unstable, the concentration declined following first-order kinetics with half-life values in the soils ranging from 2.3 to 5.0 days. The main degradation product was 1-(3,4-dichlorophenyl)-3-methylurea (DCPMU) which was more stable than the parent compound. After about 160 days, DCPMU accounted for 30 to 45% of the initial methazole concentration. Degradation of methazole and DCPMU was affected by soil temperature and moisture content. With methazole, half-lives in one soil at field capacity moisture content and temperatures of 25, 15 and 5°C were 3.5, 8.7 and 31.1 days respectively. The half-life at 25°C was increased to 5.0 days at 50% of field capacity and 9.6 days at 25% of field capacity. A proportion of the initial radioactivity added to the soil could not be extracted and this proportion increased with time. After 160 days this unextractable radioactivity accounted for up to 70% of the amount applied.  相似文献   

4.
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   

5.
The degradation of [14C] benzoyl prop ethyl (SUFFIX,a ethyl N-benzoyl-N-(3,4-dichlorophenyl)-2-aminopropionate) in four soils has been studied under laboratory conditions. The major degradation product of benzoylprop ethyl at up to 4 months after treatment was its corresponding carboxylic acid (II). On further storage this compound became firmly bound to soil before it underwent a slow debenzoylation process which led to the formation of a number of products including N-3,4-dichlorophenylalanine (IV), benzoic acid, 3,4-dichloroaniline (DCA), which was mainly present complexed with humic acids, and other polar products. Although these polar products were not identified, they were probably degradation products of DCA, since they were also formed when DCA was added to soil. No 3,3′,4,4′-tetrachloroazobenzene (TCAB) was detected in any of the soils at limits of detectability ranging from 0.01-0.001 parts/million. Since N-3,4-dichlorophenylalanine (IV) and 3,4-dichloroaniline were transient degradation products of benzoylprop ethyl, the metabolism in soil of radiolabelled samples of these compounds was also studied. In these laboratory experiments the persistence of the herbicide increased as the organic matter content of the soil increased and the time for depletion of half of the applied benzoylprop ethyl varied from 1 week in sandy loam and clay loam soils to 12 weeks in a peat soil.  相似文献   

6.
Crops and soils from field trials in 1967–1970 in several countries have been analysed for residues of the triazine herbicide cyanazine (‘BLADEX’
  • 1 Shell Registered Trade Mark.
  • a or ‘FORTROL’a' 2-chloro-4-(1-cyano-1-methylethylamino)-6-ethylamino-1,3,5-triazine) and for its degradation products 2-chloro-4-(1-carbarmoyl-1-methylethylamino)-6-ethylamino-1,3,5-triazine ( II ), 2-chloro-4-(1-cyano-1-methylethylamino)-6-amino-1,3,5-triazine ( V ) and 2-chloro-4-(1-carbonyl-1-methylethylamino)-6-amino-1,3,5-triazine ( VI ). The time for the concentration of cyanazine in soils to fall to half the initial value was in the range 1.3 to 5 weeks with a mean value of 2.4 weeks. The rate of loss was not affected by sparse crop cover and there was some indication that the rate was greater under moist soil conditions. Residues of up to 0.5 part/million of ( II ) and up to 0.08 part/million of ( VI ) were detected in soils at 4 weeks from cyanazine application at 2 kg/ha. The residues of cyanazine and the degradation products declined rapidly and were 0.07 part/million or less at 16 weeks from treatment. Repeated annual applications did not lead to a detectable build up of residues in soil. Neither residues of cyanazine nor those of ( II ), ( V ) or ( VI ) could be detected in a wide range of crops harvested from soil treated in accordance with the likely recommendations and the limits of detectability were 0.01 to 0.04 part/million.  相似文献   

    7.
    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   

    8.
    The persistence of [14C] 2,4-D at a rate equivalent to 1 kg/ha was compared under laboratory conditions in samples of heavy clay, sandy loam, and clay loam at 85% of field capacity moisture and 20 ± 1°C which had either received no pre-treatment, or had been pre-treated for 7 days at the 2 μg/g level with the herbicides benzoylprop-ethyl, diclofop-methyl, dinitramine, flamprop-methyl, nitrofen, picloram, tri-allate, trifluralin, and a combination of tri-allate and trifluralin. The breakdown of [14C] 2,4-D was also studied in the same soils that had similarly received pre-treatments of 2 μg/g of the cereal seed dressing Vitaflo-DB, the insecticide, malathion, and a combination of Vitaflo-DB and malathion. In each soil type, the half-life of the 2,4-D was similar regardless of whether the soil had, or had not, received any pre-treatment, indicating that none of the chemicals investigated adversely affected the soil degradation of 2,4-D.  相似文献   

    9.
    BACKGROUND: The 2,4‐D degradation ability of the microbiota of three arable Mediterranean soils was estimated. The impact of soil moisture and temperature on 2,4‐D degradation was investigated. RESULTS: The microbiota of the three soils regularly exposed to 2,4‐D were able rapidly to mineralise this herbicide. The half‐life of 2,4‐D ranged from 8 to 30 days, and maximum mineralisation of 14C‐2,4‐D ranged from 57 to 71%. Extractable 14C‐2,4‐D and 14C‐bound residues accounted for less than 1 and 15% respectively of the 14C‐2,4‐D initially added. The highest amounts of 14C‐2,4‐D bound residues were recorded in the soil with the lowest 2,4‐D‐mineralising ability. Although all three soils were able to mineralise 2,4‐D, multivariate analysis revealed that performance of this degrading microbial activity was dependent on clay content and magnesium oxide. Soil temperature affected the global structure of soil microbial community, but it had only a moderate effect on 2,4‐D‐mineralising ability. 2,4‐D‐mineralising ability was positively correlated with soil moisture content. Negligible 2,4‐D mineralisation occurred in all three soils when incubated at 10 or 15% soil moisture content, i.e. within the range naturally occurring under the Mediterranean climate of Algeria. CONCLUSION: This study shows that, although soil microbiota can adapt to rapid mineralisation of 2,4‐D, this microbial activity is strongly dependent on climatic parameters. It suggests that only limited pesticide biodegradation occurs under Mediterranean climate, and that arable Mediterranean soils are therefore fragile and likely to accumulate pesticide residues. Copyright © 2009 Society of Chemical Industry  相似文献   

    10.
    The acute oral toxicity of chlorfenvinphos [2-chloro-1-(2′, 4′-dichlorophenyl)vinyl diethyl phosphate] was measured in pigeon (Columba livia), pheasant (Phasianus colchicus), and quail (Coturnix coturnix japonica) and the compound was shown to be particularly toxic to pigeons. Additionally, all three species were fed chlorfenvinphos at 100 ppm in their diet for two or four weeks and esterase measurements were made by conventional and electrophoretic methods on extracts of liver, kidney and brain. The conventionally measured esterase inhibition correlated well with the acute oral toxicity figures. A more detailed study of the histochemically stained electrophoregams showed some discrepancies compared with conventional methods but offered a possible explanation of the inter-species toxicity difference in that it revealed differential inhibition of some brain iso-esterases in pigeon but not in pheasant or quail.  相似文献   

    11.
    The spatial variability in the mineralisation rate of linuron [N-(3,4-dichlorophenyl)-N'-methoxy-N'-methylurea] was studied within a previously treated Danish agricultural field by sampling soils from eleven different plots randomly distributed across an area of 20 x 20 m. The soils were characterised with respect to different abiotic and biotic properties including moisture content, organic matter content, pH, nutrient content, bacterial biomass, potential for mineralisation of MCPA [(4-chloro-2-methylphenoxy)acetic acid] and linuron. Five soils had a potential for mineralisation of linuron, with 5-15% of the added [ring-U-14C]linuron metabolised to 14CO2 within 60 days at 10 degrees C, while no extensive mineralisation of linuron was observed in the six remaining soils within this period. A TLC analysis of the methanol-extractable residues showed no development of 14C-labelled metabolites from linuron in any of the samples. Multivariate analysis was conducted to elucidate relationships between the intrinsic properties of single soil samples and initial rate of linuron mineralisation. The analysis indicated that important soil parameters in determining the spatial heterogeneity included the C(total)/N(total) ratio, pH and the water-extractable potassium contents, with the first of these highly negatively correlated and the last two highly positively correlated to the initial linuron mineralisation rate. This study shows that enhanced biodegradation of linuron may develop with successive field treatments, but that considerable in-field spatial heterogeneity in the degradation rate still exists. Combined with a parallel enrichment study focused on the underlying microbial processes, the present results suggest that intrinsic soil properties affect the linuron-metabolising bacterial population and thereby determine the spatial variability in the linuron mineralisation activity.  相似文献   

    12.
    Aqueous solutions of dichlorprop were irradiated under different conditions of pH, wavelength and oxygenation. The photochemical behaviour was found to be complex and many photoproducts were formed. However, at low concentrations the main photoproducts were 4-chloropyrocatechol, 2-chlorophenol, 4-chlorophenol and 2,4-dichlorophenol. Some other photoproducts were identified, namely 2-(4-chloro-2-hydroxyphenoxy)propanoic acid, 2-(3,5-dichloro-2-hydroxyphenyl)propanoic acid and 2,4-dichlorophenyl acetate. From comparison with results previously obtained with mecoprop [2-(4-chloro-2-methylphenoxy)propanoic acid] it appears that the presence of a chlorine atom in position 2 on the ring strongly modifies the photochemical behaviour.  相似文献   

    13.
    The hydrolysis of the iso-propyl, n-butyl-and iso-octyl esters of 2,4,5-trichlorophenoxyacetic acid (2,4,5-T), the n-bytyl ester of 2,4-dichlorophenoxybutyric acid (2,4-DB) and the iso-octyl ester of 2,4-dichlorophenoxypropionic acid (2,4-DP) was studied in four prairie soils of differing textures and pH at 25±1°C. The esters were analysed using gas chromatography. After 24 h in soils at wilting point moisture, and above, less than 20% of the applied iso-propyl and n-butyl esters could be recovered from one soil type and none from the remaining three. Loss of the iso-cotyl esters was slower; however, no trace of the 2,4,5-T and 2,4-DP esters was observed in any of the moist soils after 48 and 72 h respectively. In all cases loss of all esters from air-dried soils minimal. The phenoxyalkanoic acid hydrolysis products were recovered from all soil types, treated with the various esters and identified using thin-layer chromatography.  相似文献   

    14.
    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   

    15.
    [14C]-Labelled methazole, 1-(3,4-dichlorophenyl)-3-methylurea (DCPMU), 1-(3,4-dichlorophenyl)urea (DCPU), and diuron were incubated in soil at 20°C and field capacity soil moisture content. Decomposition followed first-order kinetics; half-lives for degradation of these four compounds were 2.4, 144, 30 and 108 days respectively. The amount of DCPMU and DCPU that could be extracted decreased with time and the decrease was accompanied by the generation of an equivalent amount of 14CO2. This was not so in the studies with diuron and methazole, however, and the decrease in the concentrations of radioactivity extracted from soil treated with these compounds could not be entirely accounted for as carbon dioxide. It is concluded that the unextractable radiochemical that was present was DCPMU. Methazole appeared to be degraded through DCPMU to 3,4-dichloroaniline (DCA) with the production of only traces of DCPU.  相似文献   

    16.
    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   

    17.
    The degradation of the pyrethroid insecticide cypermethrin and the geometric isomers NRDC 160 (cis-) and NRDC 159 (trans-) in three soils has been studied under laboratory conditions. Samples of the insecticides labelled separately with 14C in the cyclopropyl and benzyl rings were used. The rate of degradation was most rapid on sandy clay and sandy loam soils, 50% of the NRDC 160 and NRDC 159 applied to both soils being decomposed in 4 weeks and 2 weeks respectively. The major degradative route in all soils was hydrolysis of the ester linkage leading to the formation of 3-phenoxybenzoic acid and 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid; soil treated with the cis-isomer (NRDC 160) was found to contain both cis- and trans-isomer forms of the cyclopropanecarboxylic acid. Further degradation of these carboxylic acids was evident since 14CO2 was released from cyclopropyl- and benzyllabelled cypermethrin in amounts equivalent to 24 and 38% of the applied radioactivity over a 22 week period. A minor degradative route was ring-hydroxylation of the insecticide to give an α-cyano-3-(4-hydroxyphenoxy)benzyl ester followed by hydrolysis of the ester bond. Under waterlogged conditions the rate of hydrolysis of cypermethrin on sandy loam soil was slower than under aerobic conditions and 3-phenoxybenzoic acid accumulated in the anaerobic soil.  相似文献   

    18.
    Studies of the degradation of the pyrethroid insecticide cypermethrin (NRDC 149) and its cis- and trans-isomers (NRDC 160 and NRDC 159, respectively), have been extended. In soils stored in the laboratory for up to 52 weeks, cypermethrin continued to be degraded by hydrolysis and oxidation. A previously unidentified product has now been identified as the dicarboxylic acid 3-(2, 2-dichlorovinyl)-1-methylcyclopropane-1, 2-dicarboxylic acid. Comparative experiments carried out under indoor and outdoor conditions showed that essentially the same products were formed under these different conditions. However, α-carboxy-3-phenoxybenzyl 3-(2, 2-dichlorovinyl)-2, 2-dimethyl-cyclopropanecarboxylate was one minor product detected only under outdoor conditions. Evidence is presented for the further degradation of bound residues arising in soil from cypermethrin treatments. There was limited uptake of the radiolabel into wheat grown in soil containing radiolabelled bound residues.  相似文献   

    19.
    The degradation of the wild oat herbicide flamprop-methyl [MATAVEN, methyl (±)-N-benzoyl-N-(3-chloro-4-fluorophenyl)-2-aminopropionate] was studied in soils stored under anaerobic conditions. Comparative experiments were carried out in which soil was either covered with water or stored in an atmosphere of nitrogen. Under these anaerobic conditions, the major product was the carboxylic acid analogue (II) of flamprop-methyl, which was also a major degradation product formed in soil stored under aerobic conditions. However, the 2-, 3-, and 4-hydroxy-benzoyl analogues of II were also detected in soils stored under nitrogen or water and they were present in highest concentrations in the waterlogged soil. A further new product was also detected in waterlogged soil and it was shown to be N-benzoyl-N-(3-chloro-4-hydroxyphenyl)-2-aminopropionic acid. Although no hydroxylated derivatives of flamprop-methyl were detected in soils stored under aerobic conditions, it is possible that they were formed but underwent further degradation.  相似文献   

    20.
    Prediction of the fate of pesticides in soil is of interest from an environmental (pollution) as well as an agricultural (efficacy, carryover) viewpoint. Two environmental parameters that control microbial degradation of pesticides in soil are moisture and temperature. This study was designed to quantify the impact of soil water content and temperature on microbial degradation rates of the insecticide carbofuran (2, 3-dihydro-2, 2-dimethylbenzofuran-7-yl methyl-carbamate). Carbofuran degradation was determined by monitoring the [ 14 C] carbondioxide production from soils amended with [carbonyl- 14 C]carbofuran. Soils were incubated at seven soil-water tensions over the range of 0–03 to 1–5 MPa, and at five temperatures (10°C to 30°C). The sigmoidal degradation kinetics observed from these incubations were modeled using a general saturation model. For the moisture experiments, maximum rate of hydrolysis and half-life (DT50) were accurately modeled by an exponential relationship. The response of carbofuran degradation to temperature was also well described by an exponential relationship, from which it was estimated that the Q10 associated with the maximum rate was 1.68, and the Q10 for DT50 was 1–89.  相似文献   

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