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1.
The metabolism of O,S-dimethyl propionyl- and hexanoylphosphoramidothioate was investigated in the white mouse and house flies. Compared to the hexanoylphosphoramidothioate, the propionyl analog is approximately 35-fold more toxic to house flies and is 10-fold less toxic to mice. On a percentage basis, substantially larger amounts of methamidophos were detected in house flies treated topically with the propionylphosphoramidothioate than in flies treated with the hexanoyl derivative. The reverse was evident in the case of the mouse where much larger amounts of methamidophos were formed after oral treatment with the hexanoylphosphoramidothioate. Minor amounts of other metabolic products also were detected, including an unknown from the hexanoylphosphoramidothioate. Metabolism of the S-methyl moiety to carbon dioxide appeared to be a major pathway for metabolic degradation of both compounds in both the white mouse and house fly. The difference in toxicity of the two acylphosphoramidothioates to the mouse and house fly is attributed to difference in the amounts of methamidophos formed in the animals.  相似文献   

2.
The residues and metabolism of methidathion [S-(2, 3-dihydro-5-methoxy-2-oxo-1, 3, 4-thiadiazol-3-ylmethyl) O, O-dimethyl phosphorodithioate] and its secondary metabolites: demethyl-methidathion [S-(2, 3-dihydro-5-methoxy-2-oxo-1, 3, 4-thiadiazol-3-ylmethyl) O-methyl O-hydrogen phosphorodithioate] ( IV ), the sulphide (2,3-dihydro-5-methoxy-3-methylthiomethyl-1,3,4-thiadiazol-2-one) ( I ), tsulphoxide(2,3-dihydro-5-methoxy-3- methylsulphinylmethyl-1,3,4-thiadiazol-2-one) ( II ) and the sulphone (2,3-dihydro-5-methoxy-3-methylsulphonylmethyl-1,3,4-thiadiazol-2-one ( III ) were studied in laboratory-treated tomato fruit. The metabolites and residues of methidathion were determined for the applied doses of 1, 7 and 14 mg of methidathion kg?1 of fruit. Methidathion was metabolised extensively over a 14-day period. The amount of metabolites formed was a function of both the applied dose as well as the time after application. Major water-soluble metabolites were found to be IV and the cysteine conjugate S-(2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-ylmethyl)-L-cysteine ( VI ). The chloroform-soluble metabolites were identified as the oxygen analogue of methidathion [S-(2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-ylmethyl) O, O-dimethyl phosphorothioate] ( V ), the sulphoxide II , and the hydroxy compound 2,3-dihydro-3-hydroxymethyl-5-methoxy-1,3,4-thiadiazol-2-one. The oxygen analogue of methidathion ( V ) was found in small amounts, corresponding to <5% of the added methidathion. Demethyl-methidathion ( IV ) appeared to be a precursor in the formation of the cysteine conjugate VI . The sulphide I seemed to be more reactive in forming the cysteine conjugate than the sulphoxide II or the sulphone III .  相似文献   

3.
The in vivo metabolism of [14CH3S]- and [14CH3O]O,O,S-trimethyl phosphorothioate (OOS) was followed in rats after oral administration of threshold or LD50 toxic doses of 20 or 60 mg/kg. Similar metabolic studies were conducted with coadministration of 1% O,O,O-trimethyl phosphorothionate (OOO), which prevented all signs of delayed toxicity, including weight loss. When administered alone, OOS was metabolized mainly (50–60%) via removal of the CH3S moiety, which was largely converted to expired CO2. Approximately 20% of the compound was O-demethylated, presumably by conjugation with glutathione, and then further metabolized to CO2. Major urinary products were identified as O,O-dimethyl phosphoric acid (50–60%) and O,S-dimethyl phosphorothioic acid (～20%). Coadministration of OOO caused a slight decrease (～5%) in the cleavage of the CH3S moiety, indicated by a reduction in 14CO2 from [14CH3S]OOS and a quantitatively similar increase in the formation of O,S-dimethyl phosphoric acid. Limited pharmacokinetic studies indicated that OOS was rapidly absorbed and distributed throughout the body. Coadministration of 1% OOO caused a slight increase in the blood half-life of parent OOS when administered at 60 mg/kg. It was concluded that a small proportion of the cleavage of the CH3S moiety from OOS is involved in the intoxication process, and that this intoxication reaction is specifically inhibited by OOO.  相似文献   

4.
The inhibitory effects on liver microsomal carboxylesterases and erythrocyte membrane esterases produced by an impurity of malathion was investigated. Treatment of rats with an impurity of malathion, O,O,S-trimethyl phosphorothioate (OOS-Me), and its structural analog O,O-dimethyl S-ethyl phosphorothioate (OOS-Et) inhibited liver microsomal malathion and phenthoate carboxylesterases. The inhibition lasted for at least 7 days following a single oral administration of OOS-Me. These treatments inhibited acetylcholinesterase (AChE) and (Na+ + K+)-dependent ATPase of erythrocyte membranes which persisted at least 3 days. OOS-Et was a more potent inhibitor of all the esterases examined than OOS-Me. Pretreatment of rats with a metabolic inducer, phenobarbital, or a metabolic inhibitor, piperonyl butoxide, had no effect on such inhibitory effects on liver microsomal carboxylesterases produced by OOS-Me or OOS-Et.  相似文献   

5.
A simple and rapid procedure is described for the qualitative and quantitative analysis of metabolites of malathion and other insecticides. The omission of an extraction at low pH, and mild conditions of anion-exchange chromatography on QAE-Sephadex prevent the degradation of a malathion metabolite, S-(1-carboxy-2-ethoxycarbonyl)-ethyl O,O-dimethyl phosphorothioate (malaoxon α-carboxylic acid), which takes place under strongly acid conditions. Disadvantages of the commonly used fractionation of malathion and malaoxon metabolites based on partitioning are discussed.  相似文献   

6.
O,S-Dimethyl phosphoramidothiolate, the insecticide methamidophos, is converted oxidatively into a potent anti-cholinesterase agent by the action of m-chloroperbenzoic acid. The active intermediate is not stable enough to be isolated. From some chemical evidence, the sulfoxide, i.e., dimethyl phosphoramidothiolate S-oxide, is most probably the active intermediate. A similar activation may occur by biological oxidation.  相似文献   

7.
In Louisiana, Cercospora leaf blight (CLB) of soybean is primarily caused by Cercospora cf. flagellaris, which can be detected in asymptomatic leaves as early as V3 (third trifoliate) growth stage, while symptoms appear around R5 (beginning seed). The fungus produces cercosporin, an important virulence factor, the in vitro production of which is significantly reduced in the absence of simple sugars. Our objective was to investigate the role of foliar simple sugars and endophytic bacteria in CLB symptom onset. C. cf. flagellaris was cultured in filter-sterilized, untreated extracts made from asymptomatic R2 and R5 leaves; in extracts treated with chloroform to isolate hydrophilic molecules, including simple sugars; or with antibiotics to assess the role of endophytic bacteria. Endophytic bacteria were also isolated from leaves and leaf extracts and their interaction with C. cf. flagellaris was investigated. The fungus produced more cercosporin in total R5 and simple sugar-amended R2 leaf extracts, than in R2 leaf extracts. Furthermore, it produced more cercosporin in chloroform-treated R5 leaf extracts, which contained significantly higher levels of simple sugars, especially fructose, than the R2. To our knowledge, this is the first reported connection between foliar sugar content and cercosporin production. Additionally, morphologically diverse bacteria were isolated from different stages of soybean development. Also, bacterial endophytes in R5 leaf extracts and Paenibacillus polymyxa, isolated from R2 leaves, significantly reduced the growth of C. cf. flagellaris. These findings implicated soybean leaf fructose in CLB development and highlighted the potential of using foliar bacterial endophytes for CLB management.  相似文献   

8.
Malathion enantiomers were synthesized by nucleophilic substitution of O,O-dimethyl dithiophosphoryl anion to diethyl (R)- or (S)-2-bromosuccinate. Malaoxon enantiomers were obtained from optically active malathions in thiono–thiolo rearrangement with 65% HNO3. Desmethylation of malathion enantiomers by triethylamine, following the remethylation using methyl iodide gave isomalathion diastereomeric pairs. Physicochemical characteristics of the compounds obtained, and their influence on rats and some species of arthropods, are presented. © 1998 SCI  相似文献   

9.
The prolonged use of dimethoate, introduced into Denmark to control houseflies (Musca domestica L.) that had become resistant to parathion and diazinon, resulted ultimately in dimethoate resistance. Selection with dimethoate led to the disappearance of the hydrolytic phosphatase, a major mechanism of resistance to parathion and diazinon, and its replacement by the acetylcholinesterase AChER with somewhat decreased sensitivity to inhibition by organophosphorus (OP) insecticides. The hydrolytic phosphatase probably disappeared because low substrate turn-over made it ineffective against dimethoxon (O, O-dimethyl S-methylcarbamoylmethyl phosphorothioate, also known as omethoate). which accumulates at higher concentrations than paraoxon (diethyl4-nitrophenyl phosphate) in the haemolymph. Dimethoate selected AChER preferentially because it improved the chances of houseflies surviving against the relatively poor AChE inhibitor dimethoxon, whereas its relatively small insensitivity to OP insecticides, unimportant against good inhibitors such as paraoxon, prevented its selection by parathion.  相似文献   

10.
BACKGROUND: Leaf‐cutting ants are considered to be one of the most important pest species of the New World. Until now, control strategies against these leaf‐cutting ants have mainly been synthetic chemicals. The aim of the present study was to test the action of several plant extracts quoted as an example by TRAMIL participative surveys for their insecticidal properties on adult major workers of Acromyrmex octospinosus. Three tests were used to that end: contact toxicity, repellent test and ingestion bioassay. Six traditional plant uses recommended by interviewed people in surveys were tested: (1) maceration of Mammea americana fresh crushed seeds; (2) decoction of Nerium oleander fresh leaves; (3) Nerium oleander dried leaf water juice; (4) decoction of Nicotiana tabacum dried leaves; (5) Trichillia pallida dried leaf water juice; (6) decoction of Rollinia mucosa dried seeds. RESULTS: Two plant extracts with contact toxicity (Mammea americana and Nicotiana tabacum), six plant extracts with repellent activity and four plant extracts with ingestion toxicity (Mammea americana, Nicotiana tabacum and both extracts of Nerium oleander) were found. CONCLUSION: The data presented in this study showed that plant extracts cited by TRAMIL ethnopharmacological surveys have the potential to control the leaf‐cutting ant, Acromyrmex octospinosus. In particular, the Mammea americana extract, with its natural low repellent effect and its high toxicity by ingestion, and Nerium oleander extracts, with their natural delay action, are possibly the best extracts for the control of these ants. Copyright © 2011 Society of Chemical Industry  相似文献   

11.
Nematicidal activity of the leaf powder, leaf extracts and formulated leaf extracts of Myrtus communis, an evergreen shrub that is widely distributed in Israel and other Mediterranean countries, was evaluated using the root‐knot nematode Meloidogyne javanica in in vitro and pot experiments. Leaf powder added to sand at 0·1% (w/w) reduced the number of juveniles recovered from the sand by more than 50%. Reduction in galling index and number of nematode eggs on tomato roots was also observed by incorporating the leaf powder at 0·1–0·4% (w/w) in the soil in pot experiments. Leaf powder extracts with methanol or ethanol showed the highest nematicidal activity among all extracts tested. Emulsifiable concentrates of leaf‐paste extract at a concentration as low as 0·005% (a.i., w/w) reduced the number of juveniles recovered from treated sand and the gall index of cucumber seedlings. The extract paste at 26 g m?2 was also effective in reducing the gall index of tomato plants in field‐plot experiments. The leaf powder at 0·2% and the formulated leaf‐paste extract at 0·02% were also nematicidal to Tylenchulus semipenetrans and Ditylenchus dipsaci, but not to Pratylenchus penetrans or Steinernema feltiae. At least three nematicidal compounds were found in the leaf extract upon fractionation by thin‐layer chromatography. The results suggest that the leaf powder and paste extract of M. communis are potential nematicides against root‐knot nematodes.  相似文献   

12.
Methamidophos (O,S-dimethylphosphoramidothioate, Monitor) is an organophosphorus, cholinesterase-inhibiting insecticide. The rate constant (ki) for inhibiting rat plasma cholinesterase (ChE) was 1.57 ± 0.03 × 103M?1 min?1, for rat erythrocyte ChE was 8.86 ± 1.10 × 103M?1 min?1, and for rat brain ChE was 6.58 ± 0.42 M?1 min?1. Brain and plasma cholinesterases spontaneously recovered from over 90% inhibition at 30 min to 50% inhibition in 4 and 14 hr, respectively. Pralidoxime increased the rate of reactivation in vitro. In vivo, rats poisoned with methamidophos exhibited signs of cholinergic stimulation. The LD50 of ip methamidophos in male rats was 15 ± 0.7 mg/kg. Pralidoxime (60 mg/kg) and atropine (10 mg/kg) given with the methamidophos increased the LD50 to 52 ± 4.9 mg/kg and 60 ± 0.4 mg/kg, respectively. In rats given 12.5 mg methamidophos (an LD20), ChE activity was depressed 95 ± 12.5% in plasma, 92 ± 0.6% in stomach, and 88 ± 1% in brain at 1 hr after injection. At 48 hr after injection ChE activity had returned to 60% or more of control values in each of the tissues. Administration of a single dose of 60 mg/kg of pralidoxime along with methamidophos did not increase ChE activities at the times and places it was measured.  相似文献   

13.
Losses in serological reactivity of Papaya leaf distortion mosaic virus (PLDMV) were demonstrated. An antibody, IgG-papaya, raised against PLDMV purified from papaya (Carica papaya L.) did not react with virus particles in Cucumis metuliferus leaf extracts in ELISA or SSEM-PAG (serologically specific electron microscopy using protein A-gold). In addition, IgG-papaya and IgG- Cucumis raised against PLDMV purified from C. metuliferus did not react with virus particles in papaya leaf extracts after western blotting. From results of electrophoresis, the coat protein (CP) of PLDMV purified from papaya had degraded and migrated in two bands. Similar degradation was also observed when virus purified from C. metuliferus was treated with papain. These results indicated that the CP of PLDMV purified from papaya was degraded during the purification process by papain in the host plant. IgG-papaya was reactive to papain-degraded CP, while IgG-Cucumiswas reactive to both intact and degraded CP. Modified serological methods using antipain (a protease inhibitor) or papain were established to detect PLDMV. Received 16 February 2001/ Accepted in revised form 26 September 2001  相似文献   

14.
The allelopathic potential of Mikania micrantha H.B.K. to affect the seed germination and seedling growth of Coix lacryma‐jobi L. was investigated. Water‐soluble allelopathic substances were found in the water extracts of M. micrantha. The effect of the water extracts on the seed germination and seedling growth of C. lacryma‐jobi was concentration‐dependent. The water extracts from the different plant parts (leaf, stem, and root) of M. micrantha differed in their effect on the germination and seedling growth of C. lacryma‐jobi, with the effect of the leaf extract being the least inhibitory. The malondialdehyde (MDA) content in the C. lacryma‐jobi seedlings increased by 64%, 45%, and 52% of the control with increasing concentrations of the extracts of the root, stem, and leaf (80, 400, and 400 g L?1, respectively). The extract from the M. micrantha roots significantly increased the catalase (CAT) activity of the C. lacryma‐jobi seedlings (48% and 54% of the control at the concentrations of 20 g L?1 and 80 g L?1, respectively). The extracts from the leaves and stems at low concentrations increased the CAT activity, but at high concentrations, the extracts decreased the CAT activity. The extracts from the roots, stems, and leaves at concentrations of 80, 400, and 400 g L?1 also significantly decreased the peroxidase (POD) activity of the C. lacryma‐jobi seedlings to 27%, 52%, and 34% of the control, respectively. These results indicate that the water extracts of M. micrantha could inhibit the seed germination and seedling growth of C. lacryma‐jobi through the regulation of anti‐oxidase activity, such as POD and CAT in the cells. The growth inhibition of the C. lacryma‐jobi seedlings is probably related to injury after oxidization of the cell membranes with the increase of MDA content.  相似文献   

15.
The in vivo metabolism of phenthoate (O,O-dimethyl S-[α-(carboethoxy)benzyl]phosphorodithioate) was followed in rats after oral administration of a nontoxic dose of 100 mg/kg. The same metabolic study was conducted following coadministration of 0.5% O,S,S-trimethyl phosphorodithioate (OSS-Me). When administered alone, phenthoate was metabolized principally by carboethoxy ester hydrolysis and cleavage of the PO and CS bonds, resulting in at least six metabolites. The primary urinary metabolite excreted was phenthoate acid. Coadministration of 0.5% OSS-Me did not alter the types of metabolites excreted. However, a reduction of the carboxylesterase-catalyzed product (phenthoate acid) was observed, indicating that the enzyme responsible for the major pathway of phenthoate detoxication was inhibited. Alternate detoxication processes did not compensate for the reduction in carboxylesterase-catalyzed detoxication. It was concluded that inhibition of the carboxylesterase enzymes is the major cause of the potentiation of phenthoate toxicity by OSS-Me.  相似文献   

16.
The susceptibilities to methamidophos as well as the kinetic and inhibitory parameter of acetylcholinesterases (AChE) and the activities of carboxyestsrases (CarE) and glutathione-S-transferases (GST) were studied in 18 species field populations of insects collected in Fuzhou, China during April and May 2000 and 2001. The insect species included five hymenopteran endoparasitoids, one hymenopteran exoparasitoid, one hymenopteran hyperparasitoid, one dipteran predator, four coleopteran predator ladybirds, six herbivorous pest insects of lepidoptera, diptera, homoptera, and coleoptera, respectively. There existed significant correlations between the susceptibility to methamidophos and the ki values of AChE to methamidophos, dichlorvos, and carbofuran and between the ki and Vmax values of AChE among 18 species of insects. The six herbivorous pests and four ladybirds showed significantly low ki and Vmax values of AChE compared to the seven parasitoids and predator Epistrophe balteate. It was difficult to correlate the susceptibility to methamidophos or the ki values with the Km values of AChE, or with the activity of CarE and GST. The activities of CarE and GST varied depending on the different insect species. Significant synergisms of piperonyl butoxide (PB), triphenyl phosphate (TPP), and diethyl maleate (DEM) with methamidophos were observed in 14 pest insects and their natural enemies. Synergisms of PB were found to be the greatest. Reduced ki values suggested that insensitive AChE might play a critical role in the tolerance to methamidophos in the 18 insect species. The detoxification enzymes, mixed-function oxidase (MFO), CarE, and GST, were believed to be involved in the tolerance to methamidophos. MFO might play the most important role, and CarE or GST might be important in the tolerance in some insect species. Different models of tolerance to methamidophos and enzymatic potential were existed in parasitoids, predators, and herbivores based on the different selection of insecticide pressure (either directly by exposing to the spray in the field, or indirectly by the insecticides penetrated into the body of host insects) as well as different ecological and biological habitats.  相似文献   

17.
Dimethoate [O,O-dimethyl S-(N-methylcarbamoylmethyl) phosphorodithioate] was oxidatively metabolized by primary human embryonic lung cells in culture. Over 95% of the recovered radioactivity after incubation with 14C-labeled dimethoate resulted from oxidative metabolites, with the remainder being water soluble. Thus, oxidative metabolism of dimethoate predominated over hydrolytic metabolism in the cell culture system, in contrast to the whole rat where the opposite is true. The sequence of reactions was similar to that found in rats. Dimethoate was desulfurated to yield dimethoxon and both compounds were N-demethylated. Metabolism of dimethoate in mouse fibroblast L-929 cell cultures revealed up to 35% of dimethoate carboxylic acid as the only compound other than dimethoate present.  相似文献   

18.
The in-vitro metabolism of O,O-diethyl S-(N-methylcarbamoymethyl) phosphorodithioate in mouse liver was studied. The major route of metabolism was via the mixed-function oxidases present in the microsomal fraction, which formed the oxygen analogue, O,O-diethyl hydrogen phosphorothioate and diethyl hydrogen phosphate upon addition of nicotinamide-adenine dinucleotide phosphate (NADPH). In the absence of NADPH, the carboxylic acid analogue (S-carboxymethyl O,O-diethyl phosphorodithioate) was isolated only from the microsomal fraction. Addition of glutathione to the 100 000 g supernatant resulted in no metabolism of the parent compound. However, addition of glutathione to the 10 000 g supernatant resulted in the carboxylic acid formed by amidase activity being further metabolised to O,O-diethyl hydrogen phosphorodithioate by a glutathione-dependent reaction.  相似文献   

19.
建立了气相色谱-质谱法同时检测烟叶和土壤中丁硫克百威及其代谢产物(克百威和3-羟基克百威)残留量的分析方法。土壤样品用丙酮-石油醚[V(丙酮)∶V(石油醚)=1∶4]混合溶液提取,无需净化;鲜烟叶样品用丙酮-乙腈[V(丙酮)∶V(乙腈)=1∶9]混合溶液提取;烤后烟叶用乙腈提取。鲜烟叶和烤后烟叶提取液经旋转蒸发浓缩后,用弗罗里硅土柱净化。结果表明:在0.05~1 mg/kg添加水平下,丁硫克百威及其代谢产物的平均回收率在74%~99%之间,相对标准偏差(RSD,n=5)在1.5%~9.2%之间。该方法的前处理相对于萃取过程较简单,其准确度、精密度和灵敏度均符合农药残留分析与检测的技术要求,适合于丁硫克百威及其代谢产物在烟叶和土壤中的残留分析与检测。  相似文献   

20.
BACKGROUND: Pesticides in air have become of increasing concern in recent years. This study examined downwind air concentrations of carbofuran, methamidophos, mancozeb and diquat dibromide resulting from spray drift within 24 h of application, within 100 m of potato fields. RESULTS: Concentrations ranged from less than 0.05 µg m?3 in prespray samples to 6.37 µg m?3 for methamidophos at 3 h post‐spray. For most applications, air concentrations decreased with distance from the field and with time after application. Methamidophos concentrations in the air downwind continued to increase up to 3 h after spray. Air concentrations during spray were positively correlated with application rate (r = 0.904), and air concentrations at 1 h and 3 h post‐spray were positively correlated with vapour pressure (r = 1.000 and r = 0.999 respectively). Carbofuran, methamidophos and diquat dibromide concentrations during spray were above some Canadian and international health protection guidelines. CONCLUSION: Although pesticide air concentrations measured in this study are generally consistent with other studies, maximum concentrations are greater than those that have been measured elsewhere, and some are above published air quality guidelines. An evaluation of the degree of risk posed by these and other pest control products to human and wildlife receptors is recommended. Copyright © 2009 Crown in the right of Canada. Published by John Wiley & Sons, Ltd.  相似文献   

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