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1.
Daily 75 mg/kg phenobarbital ip injections for 3 days or 25 ppm dieldrin in the diet of mice for 14 days caused an increase in liver cytochrome P-450 and blood B-esterase. Liver A-esterase was not significantly increased. Under in vitro conditions, phenobarbital and dieldrin induced the oxidative as well as hydrolytic metabolism of dicrotophos, dimethoate, and phosphamidon by liver homogenates or combined microsomes plus 105,000g supernatant fractions. The concentration of dimethoxon was increased more than fourfold by the pretreatments after incubation for 4 hr at 37.5°C with NADPH added. The organophosphorus insecticides used in this study were not metabolized as well by the liver microsomes alone or 105,000g supernatant alone, as by the combination of microsomes and 105,000g supernatant. Under in vivo conditions in mice, phenobarbital and dieldrin treatments increased the urinary recovery of metabolites in the initial 6 hr after [14C]carbonyl-dimethoate or [14C]N-ethyl-phosphamidon administration. Analysis of urine showed that the inducers caused a more than sixfold increase in dimethoxon recovered and twofold increase in water-soluble nontoxic metabolites within 6 hr after dimethoate administration. With phosphamidon both inducers increased the rate of metabolism, and the total recovery in aqueous and chloroform fractions was decreased. These results suggest that increased dimethoate toxicity after phenobarbital and dieldrin treatments in whole animals results from stimulation of the activation of dimethoate to dimethoxon, while the increase in hydrolytic products after both pretreatments results in decreased toxicity of the direct acetylcholinesterase inhibitors, dicrotophos and phosphamidon.  相似文献   

2.
N-Hydroxymethyl [carbonyl-14C] dimethoate (0.43 ppm) and N-desmethyl [carbonyl-14C] dimethoate (0.50 ppm) were stem-injected into bean plants (Phaseolus vulgaris) in two separate experiments. Plants were harvested periodically, extracted, fractionated, and analyzed for metabolites. The resulting pattern of metabolites formed from the administration of these two compounds was different. Radioactivity was not detected in the organic fraction 2 days after N-desmethyl dimethoate administration. N-Desmethyl dimethoate was rapidly broken down to dimethoate carboxylic acid and other polar metabolites, then further degraded into materials which became part of the plant constituents. N-Hydroxymethyl dimethoate was quite stable in the plant. Most of the material not remaining as parent became rapidly conjugated and constant levels of conjugate were maintained. Very little radioactivity was bound in the plant marc. The metabolic pathway of these compounds is as follows: N-hydroxymethyl to the glucoside or N-desmethyl derivative; the N-desmethyl metabolite degrades primarily to the carboxylic acid but also to N-desmethyl dimethoxon, either of which in turn may be degraded to dimethoxon carboxylic acid. The conversion of -NHCH2OH to -NH2 is a slow reaction so that conjugation becomes the route of choice when the plant is treated with N-hydroxymethyl dimethoate.  相似文献   

3.
Abstract

Dimethoate 0.5% for 6 h was the most effective dip for suppressing the root-knot nematode, Meloidogyne incognita (Kofoid and White, 1919) (Chitwood, 1949). It was better than all the other treatments except 0.025% dimethoate for 6 h. Dimethoate at 0.1 and 0.2% and 0.2% parathion and diazinon as 6 h root-dips were phytotoxic. Diazinon controlled the nematode poorly and malathion was ineffective.  相似文献   

4.

BACKGROUND

The two‐spotted spider mite, Tetranychus urticae Koch is an important pest of cotton. We investigated the efficacy of dimethoate in controlling T. urticae by drip irrigation. Greenhouse and field experiments were carried out to determine the efficacy of dimethoate to T. urticae and the absorption and distribution of dimethoate in cotton.

RESULTS

Greenhouse results showed that cotton leaves received higher amounts of dimethoate compared with cotton roots and stems, with higher amounts in young leaves compared with old leaves and cotyledon having the lowest amounts among leaves. Field results showed the efficacy of dimethoate to T. urticae by drip irrigation varied by volume of dripping water, soil pH and dimethoate dosage. Dimethoate applied at 3.00 kg ha–1 with 200 m3 ha–1 water at weak acidic soil pH (5.70–6.70) through drip irrigation can obtain satisfactory control efficacy (81.49%, 7 days) to T. urticae, without negatively impacting on its natural enemy Neoseiulus cucumeris. The residue of dimethoate in all cotton seed samples were not detectable.

CONCLUSIONS

These results demonstrate the effectiveness of applying dimethoate by drip irrigation for control of T. urticae on cotton. This knowledge could aid in the applicability of dimethoate by drip irrigation for field management of T. urticae populations. © 2017 Society of Chemical Industry  相似文献   

5.
The metabolism of chlortoluron, (N′-(3-chloro-4-methylphenyl)-N,N-dimethylurea), propiconazole (1-[2-(2′,4′-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl-methyl]-1H-1,2,4-triazole), and metalaxyl (dl-N-(2,6-dimethylphenyl)-N-(2′-methoxyacetyl) alanine methyl ester) was investigated in suspension cultures of crop species for which differences in metabolism had been demonstrated at the intact plant level. Uptake and metabolism of chlortoluron by cultures of Italian rye-grass (Lolium multiflorum) was slow, the metabolites detected (42% of applied radioactivity after 13 days) being products of ring methyl oxidation and N-monodealkylation reactions. In sharp contrast, metabolism in a cotton (Gossypium hirsutum) suspension culture was extremely fast (72% after 4 hr) and was attributed to extensive N-didealkylation in addition to rapid ring methyl oxidation. This rate of metabolism also implied a very rapid uptake of chlortoluron by the cotton culture. 14C-labelled propiconazole became rapidly associated with cells of wheat (Triticum aestivum) and rice (Oryza sativa) following treatment of suspension cultures. Uptake was initially more rapid in the rice culture (36% of applied radioactivity after 8 h compared to 19% for wheat) which, together with a slower rate of metabolism, resulted in more unchanged propiconazole being associated with rice cells. On a parts-per-million basis these results indicated an apparent 10-fold accumulation of propiconazole in rice cells compared to 5-fold in the wheat culture. Propiconazole metabolite patterns were similar in cultures of both species and indicated side-chain hydroxylation as the principal pathway. Uptake of metalaxyl was slow in suspension cultures of both lettuce and potato (≅ 20% after 17 days). Subsequent metabolism was also slow but appeared to be limited by the poor rate of uptake. Both cultures were found to be similarly versatile with respect to metabolic attack on metalaxyl, which included ring methyl hydroxylation, aryl hydroxylation, ester cleavage, ether cleavage (O-dealkylation), and N-dealkylation (side-chain cleavage), the hydroxylation reactions being quatitatively the more important. The results for all three pesticides are compared to those obtained previously from studies with intact plants of the same species.  相似文献   

6.
为明确不同生育期豇豆上施用乐果可能产生的残留风险,以40%乐果乳油按有效成分设低（540 g/hm2）、中（600 g/hm2）和高（900 g/hm2）3个施药剂量,开展了苗期、结荚期2次施药和结荚期3次施药3种场景下的田间模拟试验,按照一定的时间间隔采集成熟豇豆样品,采用乙腈提取,C18分散净化,超高效液相色谱-串联质谱检测。结果表明:乐果和氧乐果在豇豆中的定量限均为0.01 mg/kg,在0.01~2 mg/kg添加水平下,乐果和氧乐果的平均回收率在77%~101%,相对标准偏差为3.1%~17%。距苗期最后一次施药后10 d,乐果在豇豆中的残留量各处理均低于中国国家标准中规定的最大允许残留限量（MRL）值0.5 mg/kg,最高为0.043 mg/kg;但其代谢物氧乐果残留量在施药后14 d,仅540 g/hm2的处理低于其MRL值0.02 mg/kg,施药后18 d仍有检出,最高为0.013 mg/kg。于结荚期2次和3次施药条件下,豇豆中乐果的残留量分别于施药后3 d和5 d即低于其MRL值（0.5 mg/kg）;而其代谢产生的氧乐果在施药后10 d仅540 g/hm2处理在豇豆中的残留量低于其MRL值。表明乐果使用后的残留超标风险主要源于其代谢物氧乐果。因此,建议豇豆结荚期不宜施用乐果,对其在苗期施用也应严格限制。  相似文献   

7.
Three pesticides, dimethoate, pirimicarb and fenpropimorph, had a negative impact on the colonization of a sterilized soil by a natural population of soil protozoa. Fenpropimorph has an effect at the lowest concentration applied; 25 mg litre?1. Dimethoate reduced the soil respiration significantly for about 10 days after application. In single species cultures of soil protozoa in liquid media, a flagellate Cercomonas sp., was a better test organism than a ciliate, Colpoda sp., or an amoeba, Acanthamoeba sp., with respect to interpretation of dose-response curves and ease of observation.  相似文献   

8.
The acute toxicities of two organophosphorodithioate (dimethoate and disulfoton) and two organophosphorothioate (omethoate and demeton-S-methyl) insecticides were evaluated individually and in binary combination with the herbicide atrazine using fourth-instar larvae of the aquatic midge, Chironomus tentans. Atrazine alone up to 1000 μg/L did not show significant toxicity to the midges in a 48-h bioassay. However, atrazine concentrations as low as 1 μg/L in combination with dimethoate at EC25 (concentration to affect 25% of tested midges), 100 μg/L in combination with disulfoton (EC25), and 10 μg/L in combination with demeton-S-methyl (EC25) significantly enhanced the toxicity of each organophosphate insecticide. In contrast, atrazine concentrations of 10 μg/L and above in combination with omethoate (EC25) significantly decreased the toxicity of the insecticide. Biochemical analysis indicated that increased toxicity of dimethoate, disulfoton, and demeton-S-methyl in binary combination with atrazine correlated to the increased inhibition of acetylcholinesterase. Furthermore, cytochrome P450-dependent O-deethylation activity in the midges exposed to atrazine at 1000 μg/L was 1.5-fold higher than that in the control midges. Thus, atrazine appeared to induce cytochrome P450 monooxygenases in the midges. Elevated cytochrome P450 monooxygenase activity may increase the toxicities of dimethoate, disulfoton, and demeton-S-methyl by enhancing the oxidative activation of dimethoate into omethoate, and disulfoton and demeton-S-methyl into their sulfoxide analogs with increased anticholinesterase activity. In contrast, atrazine reduced the toxicity of omethoate possibly by enhancing the oxidative metabolic detoxification since omethoate does not require oxidative activation.  相似文献   

9.
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10.
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   

11.
The antioxidant responses of Solanum nigrum L. cell suspension cultures to metalaxyl exposure were investigated. An increase in lipid peroxidation and hydrogen peroxide content, for both concentrations tested (20 mg L−1; 40 mg L−1) revealed the response of oxidative metabolism of cell suspensions to metalaxyl. Superoxide dismutase (SOD; EC 1.15.1.1), catalase (CAT; EC 1.11.1.6) and ascorbate peroxidase (APX; EC 1.11.1.11) activities increased, particularly in the highest concentration of metalaxyl used. An analysis by non-denaturing polyacrylamide gel (PAGE) followed by staining for enzyme activity, revealed seven SOD isoenzymes, two CAT isoenzymes, and nine APX isoenzymes. Metalaxyl levels were quantified in the culture medium and results suggest that suspension cells were able to accumulate and/or degrade the fungicide five hours after exposure. SOD, CAT and APX isoenzymes were differently affected by the metalaxyl treatment. Results suggest that the higher concentration of metalaxyl induced oxidative stress to cell suspension cultures of S. nigrum.  相似文献   

12.
The aim of this study was to evaluate the effects of different N-acetylcysteine doses on the tolerance to fenthion-induced oxidative stress, alterations in glutathione metabolism and cholinesterase specific activities in the liver by using freshwater fish Cyprinus carpio (Cyprinidae) as a model organism. An acute toxicity study was carried out to determine 96-h median lethal concentration of fenthion for this species (2.16 mg/L) and 80% of this concentration was applied in toxicity studies. Four groups, each containing eight fish were constituted as follows: Control group, fenthion treated group, 0.5 or 400 mg/kg NAC-injected + fenthion-treated groups. Biochemical analyses were carried out spectrophotometrically. Fenthion treatment significantly decreased total glutathione and glutathione levels, glutathione/glutathione disulfide ratio together with glutathione reductase and γ-glutamylcysteine synthetase specific enzyme activities. The higher dose of N-acetylcysteine increased the toxic effects of fenthion and γ-glutamyl transpeptidase specific activity while decreasing glutathione S-transferase specific activity. However, injection of the lower dose provided a limited protection against fenthion toxicity. In all exposure groups, lipid peroxidation increased and total protein levels decreased, while protein depletion was prevented by low dose of N-acetylcysteine application. Acetylcholinesterase and butyrylcholinesterase activities were at similar levels in the liver of C. carpio. A dose-dependent inhibition was observed in butyrylcholinesterase activity by N-acetylcysteine application. The results showed that fenthion had a significant oxidative stress inducing potential through the reduction of glutathione redox capacity. The critical point for overcoming oxidative stress by N-acetylcysteine in fenthion toxicity was the selection of the dose; N-acetylcysteine exerted its toxic effects by means of oxidative stress in fish liver at the higher dose.  相似文献   

13.
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   

14.
The microbial metabolism of N3,N3-diethyl 2,4-dinitro-6-trifluoromethyl-m-phenylenediamine (dinitramine), N-sec-butyl-4-tert-butyl-2,6-dinitroaniline (A-820), N-n-propyl-N-cyclopropylmethyl-4-trifluoromethyl-2,6-dinitroaniline (CGA-10832), and α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine (trifluralin) by Aspergillus fumigatus Fres., Fusarium oxysporum Schlecht and Paecilomyces sp. was investigated. The dinitrodiamine and dinitroanilines were most readily metabolized by Paecilomyces sp. The metabolism of dinitramine was examined in detail, and four metabolites were isolated: N3-ethyl 2,4-dinitro-6-trifluoromethyl-m-phenylenediamine; 2,4-dinitro-6-tri-fluoromethyl-m-phenylenediamine; 6-amino-1-ethyl-2-methyl-7-nitro-5-trifluoromethylbenzimidazole and 6-amino-2-methyl-7-nitro-5-trifluoromethylbenzimidazole. The presence of a dinitramine-degrading enzyme system in A. fumigatus was demonstrated. The enzyme dealkylates dinitramine and requires NADPH and Fe2+ as cofactors.  相似文献   

15.
The metabolism of a new, selectively toxic derivative of carbofuran, 2,2-dimethyl-2,3-dihydrobenzofuranyl-7 N-methyl-N-(2-toluenesulfenyl)carbamate has been investigated. The selective toxicity between insect and mammal is due to differing pathways of metabolism. Houseflies appear peculiarly suited for the rapid liberation of the toxic agent, carbofuran, from N-(2-toluenesulfenyl) carbofuran in large amounts. Metabolism in the mouse is more complex and involves a series of oxidative and hydrolytic detoxication processes which do not result in the formation of carbofuran.  相似文献   

16.
When [14C]F3-fluorodifen (2,4′-dinitro-4-trifluoromethyl diphenylether), carbonyl-[14C]CDAA (N,N-diallyl-2-chloroacetamide), and carbonyl-14C-propachlor (2-chloro-N-isopropylacetanilide) were fed to rats, 57 to 86% of the 14C was excreted via the urine within 48 hr. Although very little radioactivity was excreted in the feces of CDAA-treated rats, 15–22% of the 14C was excreted in the feces of propachlor- of fluorodifentreated rats and an average of 8% of the 14C remained in these rats 48 hr after treatment. Oxidation of the 14C label to [14C]O2 was not a major process in the metabolism of these herbicides. The only major radioactive metabolite present in the 24-h urine of fluorodifen-treated rats, 2-nitro-4-trifluoromethylphenyl mercapturic acid, accounted for 41% of the administered dose of 14C. In the metabolism of CDAA, the corresponding mercapturic acid accounted for 76% of the dose; it was the only major metabolite present in the 24-h urine. In contrast, three major metabolites were detected in the 24-h urine of propachlortreated rats, and the mercapturic acid accounted for only 20% of the dose. The mercapturic acid of each herbicide was identified by mass spectrometry.  相似文献   

17.
The absorption and metabolism of topical doses of carbaryl by larvae of the gypsy moth, Lymantria dispar (L.), were determined using 14C-ring-labeled material. Carbaryl penetration followed four distinct phases of linear absorption, i.e., 0–5 min, 5–60 min, 1–3 hr, and 3–12 hr; the absorption rates for the four phases were 2.8, 0.57, 0.07, and 0.02% per minute, respectively. Ninety percent of the total metabolism of carbaryl occurred within the first 3 hr; over the next 9 hr, metabolism was exceedingly slow with a linear rate of ca. 0.8% per hour. Carbaryl was always the major radiocarbon in the larvae and the feces, amounting to ca. 16 and 9%, respectively, at 12 hr. At 12 hr the metabolite composition was 5-hydroxy carbaryl >N-hydroxy carbaryl > 1-naphthol > 4-hydroxy carbaryl > 5,6-dihydro-5,6-dihydroxy carbaryl. Small amounts of an additional product were detected but not identified. Much of the excretion of carbaryl and metabolites occurred without conjugation. The amounts of carbaryl metabolized by second, third, fourth, and fifth instars were directly correlated with the insecticide tolerances and mixed-function oxidase activity of the various larval stages. The synergistic action of 2,6-dichlorobenzyl-2-propynyl ether and piperonyl butoxide was also correlated with inhibition of the oxidative pathway.  相似文献   

18.
The toxicity of pirimicarb, imidacloprid, dimethoate, lambda-cyhalothrin, flonicamid and spinosad to the two-spot ladybird, Adalia bipunctata, was evaluated in a laboratory study. Susceptibility of fourth instars and female adults was assessed by measuring toxicity via residual contact and ingestion through feeding on contaminated green peach aphids (Myzus persicae). Flonicamid and spinosad had no lethal effects on larvae and female adults. Pirimicarb was harmless to the predator by ingestion exposure but showed some residual toxicity at high concentrations to both larval and adult stages. Imidacloprid was highly toxic to the larval stage by residual and ingestion exposure but caused very low adult mortality when ingested through contaminated prey. Dimethoate and lambda-cyhalothrin were highly toxic to both the larval and adult stages of the ladybird. Our findings indicate that pest management programs in agricultural crops using dimethoate, lambda-cyhalothrin and, to a lesser degree, imidacloprid, are detrimental to A. bipunctata, whereas pirimicarb, flonicamid and spinosad are more compatible with the use of this predator.  相似文献   

19.
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   

20.
The larvicidal activity of a series of N-2,6-difluoro- and N-2,6-dichlorobenzoyl-N′-(4-substituted phenyl)ureas against nondiapause larvae of the rice stem borer, Chilo suppressalis Walker, was measured by topical application and oral administration methods under conditions with and without piperonyl butoxide as an inhibitor of oxidative metabolism. The effects of substituents at the anilide moiety on the larvicidal activity were analyzed quantitatively using physicochemical substituent parameters and regression analysis. The results indicate that the oxidative metabolism in the larval body which is favored by electron-donating substituents is significant in determining the activity. The activity, when the metabolic factor is eliminated, is enhanced by electron-with-drawing and hydrophobic substituents and lowered by bulky groups. The inhibitory activity against new cuticle formation of the same series of compounds was also measured using cultured integument of the rice stem borer diapause larva. The comparison of the quantitative analyses between larvicidal and integument-level activities shows that inhibition of cuticular development is the most important factor governing larvicidal activity.  相似文献   

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