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1.
BACKGROUND: With the objective of exploring the fungicidal activity of 2‐oxocyclohexylsulfonamides (2), a series of novel 2‐amino‐6‐oxocyclohexenylsulfonamides (6 to 23) were synthesised, and their fungicidal activities against Botrytis cinerea Pers. were evaluated in vitro and in vivo. RESULTS: The compounds were characterised by IR, 1H NMR and elemental analysis. Bioassay results of mycelial growth showed that compounds 6 to 23 had a moderate antifungal activity against B. cinerea. N‐(2‐methylphenyl)‐2‐(2‐methylphenylamino)‐4,4‐dimethyl‐6‐oxocyclohexenylsulfonamide (13) and N‐(2‐chlorophenyl)‐2‐(2‐chlorophenylamino)‐6‐oxocyclohexenylsulfonamide (21) showed best antifungal activities, with EC50 values of 8.05 and 10.56 µg mL?1 respectively. Commercial fungicide procymidone provided an EC50 value of 0.63 µg mL?1. The conidial germination assay showed that most of compounds 6 to 23 possessed excellent inhibition of spore germination and germ‐tube elongation of conidia of B. cinerea. For in vivo control of B. cinerea colonising cucumber leaves, the compound N‐cyclohexyl‐2‐(cyclohexylamino)‐4,4‐dimethyl‐6‐oxocyclohexenylsulfonamide (19) showed a better control effect than the commercial fungicide procymidone. CONCLUSION: The present work demonstrated that 2‐amino‐6‐oxocyclohexenylsulfonamides can be used as possible new lead compounds for further developing novel fungicides against B. cinerea. Copyright © 2011 Society of Chemical Industry  相似文献   

2.
The microsome-NADPH system of mouse liver oxidizes each of benthiocarb, butylate, cycloate, EPTC, molinate, pebulate, and vernolate herbicide chemicals to the corresponding thiocarbamate sulfoxide which is then cleaved by the liver soluble-glutathione system. These sulfoxides are also detected as transient metabolites in the liver of mice injected with EPTC, molinate, pebulate, and vernolate but not with the other three thiocarbamates. Thiocarbamate sulfones are not detected as metabolites of the thiocarbamates. Studies in vivo and in vitro with [14C]EPTC and -pebulate or their corresponding sulfoxides and/or sulfones further indicate that sulfoxidation is the initial metabolic step in cleavage of the thiocarbamate ester group. Sulfoxidation appears to be a detoxification mechanism for thiocarbamate herbicides in mammals.  相似文献   

3.
A suspension culture of isolated rat hepatocytes was used to reproduce in vitro the paraoxon-induced release of hepatic β-glucuronidase observed in vivo. After a short latent period, exposure of hepatocytes to paraoxon at 10?7 to 10?4M resulted in a typical dose-dependent response, with highest release occurring at 10?4M paraoxon. With 10?3M paraoxon, however, response was anomalous with a much-decreased enzyme release. As expected from earlier results in vivo, SV1-oxon exhibited less effect than paraoxon.  相似文献   

4.
Insect juvenile hormone (JH) mimics (JHMs) are known to have ovicidal effects if applied to adult females or eggs. Here, we examined the effects of exogenous JHMs on embryonic development of the bean bug, Riptortus pedestris. The expression profiles of JH early response genes and JH biosynthetic enzymes indicated that JH titer was low for the first 3 days of the egg stage and increased thereafter. Application of JH III skipped bisepoxide (JHSB3) or JHM on Day 0 eggs when JH titer was low caused reduced hatchability, and the embryos mainly arrested in mid- or late embryonic stage. Application of JHMs on Day 5 eggs also resulted in an arrest, but this was less effective compared with Day 0 treatment. Interestingly, ovicidal activity of synthetic JHMs was much lower than that of JHSB3. This study will contribute to developing novel insecticides that are selective among insect species.  相似文献   

5.
The fluorescent insect growth regulator 5[[[5-(dimethylamino)-1-naphthalenyl]amino]-1,3-benzodioxole (DNSAB) forms a metabolite complex with house-fly microsomal cytochrome P-450. Formation of the metabolite complex is dependent on the presence of NADPH and O2; NADH supports the reaction at a reduced rate. The presence of antibodies to house-fly cytochrome c (P-450) reductase in reaction mixtures inhibits the complex formation, indicating that the reductase is necessary for transfer of electrons from NADPH to cytochrome P-450 to complete the reaction. In the oxidized form, the metabolite complex has a single absorbance maximum at 431 nm, whereas the reduced form has two absorbance maxima at 426 (major) and 455 nm (minor). The pH of the media affects the extinction of the 426- and 455-nm Soret bands; increased pH decreases the extinction of the 426-nm band and increases the extinction of 455-nm band. Formation of the DNSAB metabolite-cytochrome P-450 complex decreases the amount of CO-reactive cytochrome P-450 by 24%. The metabolite complex is not dissociable by treatment with ferricyanide or by using centrifugation techniques. Dissociation is accomplished by addition of DNSAB to the oxidized metabolite complex. Kinetic analysis of the complex formation gives apparent Km and Vmax values at 2.55 ± 1.0 μM and 1.1 ± 0.4 × 10?2 ΔA min?1 nmol?1 cytochrome P-450, respectively. Addition of juvenile hormone [(E,E)-cis-methyl-10,11-epoxy-7-ethyl-3,11-dimethyl-2,6-tridecadienoate; JH] to the reaction medium competitively inhibits the formation of the metabolite complex giving an inhibition constant of 16 μM. DNSAB synergized the lethal effects of JH against Aedes aegypti larvae threefold; however, JH did not synergize DNSAB. These data suggest that DNSAB may acquire its hormonal qualities by complexing a species of cytochrome P-450 that metabolizes JH, thereby prolonging the in vivo lifetime of this hormone.  相似文献   

6.
Inhibition of carotenoid biosynthesis by herbicidal m-phenoxybenzamide derivatives has been investigated in a cell-free carotenogenic system from Aphanocapsa. Their target is the phytoenedesaturase reaction. Double-reciprocal plots of β-carotene biosynthesis (from 14C-labeled geranylgeranyl pyrophosphate) showed that 3-(2,5-dimethylphenoxy)-N-ethylbenzamide was a noncompetitive inhibitor of the phytoene-desaturase complex. The Ki value for cell-free inhibition of β-carotene formation was almost identical to the I50 value of intact cells. Furthermore, the influence of certain substituents on herbicidal activity has been investigated. Inhibition increased with the length of the unbranched N-alkyl chains. In addition, substituents at the phenoxy group with higher lipophilicities showed greater inhibitory activities. The presence of a phenoxy or trifluoromethyl moiety at position 3 is essential.  相似文献   

7.
Inhibition of chicken brain neurotoxic esterase (NTE) by a series of O-halogenated-phenyl-O-alkyl phenylphosphonates was studied in vitro. The “apparent” activity was found to consist of “true” NTE (sensitive to mipafox) plus a minor mipafox-resistant component. The pI50 of O-(2,6-dichlorophenyl) O-methyl phenylphosphonate for “true” NTE was 6.65, whereas it was about 3 for mipafox-resistant hydrolysis of phenyl valerate. This compound is suitable as an alternative to mipafox in the assay of “true” NTE, whereas the use of leptophos oxon gives a less accurate measure. The ethoxy analogs are about as potent in vitro as the corresponding methoxy compounds. Leptophosoxon and ethoxyleptophosoxon are more potent in vitro inhibitors than desbromoleptophosoxon. Within a like group of chlorinated phenylphosphonates, a reasonable correlation between in vitro neurotoxic esterase inhibition of the oxon and in vivo delayed neurotoxic potential by the corresponding phosphonothionate exists. In vivo inhibition of “apparent” NTE from chicken brain, studied 24 hr after an oral dose, is dose dependent for leptophos, ethoxyleptophos, and desbromoleptophos, the latter one being a very potent in vivo inhibitor. Ethoxyleptophos and leptophos have about equal in vivo esterase inhibitory properties. For desbromoleptophos and leptophos there is good agreement between the minimum dose causing delayed neurotoxicity and the dose leading to substantial inhibition of “apparent” NTE; ethoxyleptophos, on the other hand, inhibits the esterase at a dose much lower than the one which is neurotoxic. Several possible explanations for this discrepancy are considered.  相似文献   

8.
The independent modes of action of diuron and atrazine on the photochemical activities of chloroplasts (In vivo and in vitro) from the leaves of crop plants Pisum sativum and Pennisetum typhoides and the weeds Amaranthus viridis and Cyperus rotundus were investigated. Hill reaction activity (DCPIP photoreduction) of in vivo chloroplasts (chloroplasts isolated from herbicide-sprayed plants) was unaffected by treatment at sublethal or intermediate levels of diuron or atrazine while that of in vitro chloroplasts (chloroplasts incubated in the required herbicidal concentration) was severely inhibited. The ferricyanide catalyzed noncyclic photophosphorylation was markedly reduced in both the in vivo and in vitro chloroplast systems. N-Methyl phenozonium sulfate (PMS)-mediated cyclic photophosphorylation was inhibited in the in vivo system while a pronounced enhancement of activity was noticed in the in vitro chloroplasts. The rate of NADP+ photoreduction was severely inhibited in the in vitro chloroplasts. The unaffected in the in vivo system. The herbicidal effects on the photoreactions of isolated chloroplasts were compared with chloroplasts isolated from herbicide-sprayed plants.  相似文献   

9.
The metabolism in vivo and in vitro of [14C]parathion and [14C]paraoxon was studied in a susceptible (LS) and an organophosphorus-resistant (Q) strain of the sheep blowfly, Lucilia cuprina. Both strains detoxified the insecticides in vivo via a number of pathways, but the resistant strain produced more of the metabolites diethyl phosphate and diethyl phosphorothionate. No difference was found between strains in the rate of penetration of the compounds used. Also, in vitro studies showed no difference between strains in the sensitivity of head acetylcholinesterase to inhibition by paraoxon. Both the microsomal and the 100,000g supernatant fractions degraded paraoxon, but resistance in Q could be explained by the eightfold greater rate of diethyl phosphate production with or without added NADPH. Parathion was also degraded to diethyl phosphorothionate by an NADPH-requiring enzyme in microsomal preparations from both strains. However, Q produced significantly more diethyl phosphorothionate in vivo than LS. It was concluded that organophosphorus resistance in Q was due mainly to a microsomal phosphatase hydrolyzing phosphate but not phosphorothionate esters, probably enhanced by a microsomal oxidase detoxifying the latter.  相似文献   

10.
The reactivation of the rat brain muscarinic acetylcholine receptor (mACh-R) binding with dimercaptosuccinic acid (DMSA) after in vitro and in vivo inhibition by mercuric chloride (HgCl2) and methylmercuric chloride (MeHg) was investigated. Receptor binding was estimated by the potent and specific antagonist l-[3H]quinuclidinyl benzilate ([3H]QNB). Rat brain synaptosomal membranes were exposed to HgCl2 and MeHg. At 1 × 10?4M. HgCl2 caused complete inhibition of the [3H]QNB binding. The inhibition of [3H]QNB binding by HgCl2 was still higher than 50% at 1 × 10?8M. MeHg caused less inhibition of [3H]QNB binding than HgCl2. The inhibited receptors showed a significant degree of reactivation when treated with DMSA. The recovery was almost complete after MeHg inhibition or with the lower HgCl2 concentrations. Generally, the reactivation was dependent on the concentration of DMSA. When rats injected with either early or delayed doses of DMSA following administration with five consecutive daily doses (8 mg/kg body wt, Gavage method) of MeHg or HgCl2, the inhibition of [3H]QNB binding was less than untreated ones. The early treatment with DMSA decreased the inhibition of [3H]QNB binding due to MeHg or HgCl2 intoxication. However, DMSA was more effective in reducing HgCl2 inhibition than MeHg either in vitro or in vivo treatment. The ability of DMSA to reactivate the mACh-R after inhibition with the mercurials emphasizes the involvement of essential sulfhydryl groups in [3H]QNB binding sites, and also shows that these sulfhydryl groups are the primary target for the MeHg and HgCl2 inhibition of the rat brain muscarinic receptors.  相似文献   

11.
S,S-Di-isobutyl N ethylethylenebis(thiocarbamate) (R-31026) had a strong morphogenetic effect, acting by contact on the newly formed pupae of Tribolium confusum and Tribolium castaneum and thereby disrupting adult development. At a dietary concentration of 20 mg kg?1, 95% of pupae of T. confusum produced pupa-adult intermediates; T. castaneum pupae were affected to a smaller extent. Topical application with 0.002 μg per 0–24-h-old pupa of T. confusum resulted in the formation of 88% malformed intermediates. The larvae brought into contact with R-31026 were not affected and pupated normally, hence the compound differs in its activity from that of a typical juvenile hormone compound. On the other hand, the pupal morphogenetic activity of R-31026 resembles that of the typical juvenoid compound 3-[5-(4-ethylphenoxy)-3-methylpent-3-enyl]-2,2-dimethyloxirane (R-20458). The progeny of the emerging adults from pupae treated with either R-20458 or R-31026 were strongly affected. The effective dosages were far below those required for pupal morphogenetic activity. Biochemical studies showed an increase in the soluble protein fraction during the pupal stage after treatment with either R-31026 or R-20458 indicating disturbances in protein build-up. The bis(thiocarbamate) R-31026 has more favourable practical properties than R-20458 for controlling agricultural insects, because it does not prolong the larval feeding stage.  相似文献   

12.
The potency of dietary phenyltin compounds in inhibiting the growth of first and fourth instar Tribolium confusum L. larvae and the gut proteolytic activity of fourth instar larvae decreases in the order of triphenyltin chloride (Ph3SnCl) ? diphenyltin dichloride (Ph2SnCl2) ? phenyltin trichloride or tetraphenyltin. The growth retardation, which prolongs the larval stage without affecting pupation or emergence, may result from an antifeeding effect involving gut protease inhibition by Ph3Sn+ and Ph2Sn2+. Gut amylase and invertase activities are less sensitive than the protease activity to in vivo inhibition. Under in vitro conditions, relatively high concentrations of Ph3SnCl and Ph2SnCl2 are required for inhibition, the order of enzyme sensitivity is protease > amylase > invertase, and Ph2SnCl2 is more potent than Ph3SnCl. Proteins such as casein, albumin and hemoglobin, but not carbohydrates such as starch and sucrose bind Ph3Sn+ so it is inaccessible for inhibition of digestive enzymes. The level of Ph3Sn+ inhibiting gut protease in vivo is far below that necessary for in vitro inhibition of this enzyme activity. It is speculated that the in vivo inhibitory effects of Ph3Sn+ and Ph2Sn2+ on digestive enzymes may result from binding to the enzyme protein, its zymogen or to other proteins involved in production of the digestive enzymes.  相似文献   

13.
O,O,S-Trimethyl phosphorothioate (OOS), a contaminant of technical formulations of some organophosphorus pesticides, was found to be immunotoxic at subtoxic doses in female C57Bl/6 mice. Mice treated orally with acute doses of 10 mg/kg OOS show no overt toxic signs such as weight loss or malaise. In addition, the levels of serum cholinesterase was not decreased. Histopathologic investigation demonstrated no alterations in liver, lung, kidney, heart, skin, brain, spleen, or gut. The LD50 for delayed toxicity was approximately 35 mg/kg. Despite the lack of general toxic changes at doses of 5–10 mg/kg OOS, specific immunotoxic changes were found. The humoral or cell-mediated immune response of splenocytes from mice treated with 10 mg/kg OOS to in vivo immunization was diminished with respect to control animals. Responses were measured in ex vivo assays. Cytotoxic T-lymphocyte (CTL) responses were assessed by alloimmunization with the tumor P815 followed by a 51Cr release assay done ex vivo with splenic lymphocytes. Humoral responses were assessed by immunization with sheep red blood cells followed by a Jerne plaque assay to determine anti-sheep red blood cell antibody. Both cellular and humoral responses could be stimulated in vitro using cells from OOS-pretreated, primed animals, thus indicating that no permanent cellular elterations had occurred.  相似文献   

14.
Tetraphenylstibonium chloride (Ph4SbCl) at a dietary level of 500–2000 μmol/kg inhibits larval growth, gut invertase activity, pupation, and emergence of Tribolium confusum and Tribolium castaneum. Tetraphenylphosphonium chloride (Ph4PCl) in this concentration range inhibits growth and gut invertase activity without affecting pupation and emergence whereas tetraphenylarsonium chloride is essentially inactive in all respects. Triphenylstibine (Ph3Sb) but not the other triphenyl derivatives (amine, phosphine, and arsine) inhibits both larval growth and gut digestive enzyme activities (invertase and protease) in vivo. Protease but not invertase is inhibited in vitro by Ph4PCl and Ph4SbCl at 2 × 10?3M. Ph4PCl appears to act as an antifeeding agent and Ph4SbCl and Ph3Sb as more general toxicants.  相似文献   

15.
Vernolate (0, 8, 16, 31, 62, 125.0, or 250.0 ppbw) incorporated into sand inhibited the growth of wheat (Triticum aestivum L. cv Holley) at 125.0 ppbw. These growth inhibition and morphological responses were virtually identical to wheat response to EPTC at 125 ppbw. 14C from vernolate (carbonyl labeled) (125.0 ppbw) was absorbed into wheat seedlings at approximately 1.8 μM on the presumption that the 14C present was [14C]vernolate. Since the response of wheat to the thiocarbamate herbicides resembles a gibberellic acid (GA) deficiency and cell enlargement requires the presence of functional plasmalemmas and tonoplasts, the question of membrane disruption by excessive concentrations of thiocarbamate herbicides and potential reversal thereof by GA3 was studied by measuring the efflux of K+, Na+, and Mg2+. GA3 (0.003 μM) stimulated lettuce leaf disc growth in diameter and fresh weight. This GA-stimulated increase in size and weight was reversed by 1 mM EPTC. Betacyanin efflux from beet leaf tonoplasts was increased by 1 mM EPTC and this efflux was not reversed by exogenous GA3 (0.3 μM). This influence by supraoptimal EPTC concentrations was shown to be via membrane disruption, which obviated any possible GA influence by eliminating the functionality of the membranes requisite to the development of a GA response. It is concluded that viable mode-of-action studies must measure physiological responses consistent with the symptomology of herbicide responses normally observed with each herbicide at field concentrations.  相似文献   

16.
Inhibition of permethrin-hydrolyzing enzymes from larvae of the porina moth Wiseana cervinata has been examined in vivo and in vitro. Significant inhibition was shown by carbaryl and pirimiphos-methyl. 1-Dodecylimidazole substantially inhibited permethrin hydrolysis only in liver insects. The triphenylmethane dye tetrabromophenolphthalein was a moderate inhibitor only in vitro. TMDM (bis(N-dimethyl-4-aminophenyl)methane) had little effect on hydrolysis. These observations extend the range of species and substrates for which the triphenylmethane dyes and 1-dodecylimidazole are useful inhibitors of insecticide metabolism.  相似文献   

17.
The rapid interactions between the herbicide S-ethyl dipropyl thiocarbamate (EPTC) and the structurally similar herbicide protectant N,N-diallyl 2,2-dichloroacetamide (DDCA) at the level of herbicide uptake were examined in maize cell cultures. When the two compounds were given simultaneously, DDCA inhibited uptake of [14C]EPTC into maize cells measured for 30 min. A Lineweaver-Burk plot indicated this inhibition to be competitive. N,N-Diallyl 2-chloroacetamide (CDAA), a compound similar in structure to DDCA, inhibited uptake to a lesser extent. Other protectants having no similarity in structure to either DDCA or EPTC had no inhibitory effect on the uptake of EPTC. The data suggest that competition between DDCA and EPTC for a site of uptake may be related to their similarity in chemical structure. Experiments with metabolic inhibitors suggested that uptake of EPTC is not via an active transport mechanism. We suggest that competition for uptake between EPTC and DDCA may represent the first step in a complex series of interactions between the herbicide and its protectant that contributes to the protection of maize from herbicide injury.  相似文献   

18.
A series of 27 substituted thio-1,1,1-trifluoropropanones was synthesized by reacting the corresponding thiol with 1,1,1-trifluoro-3-bromopropanone. The resulting sulfides were screened as inhibitors of hemolymph juvenile hormone esterase and α-naphthyl acetate esterase activity of the cabbage looper, Trichoplusia ni, electric eel acetylcholinesterase, bovine trypsin, and bovine α-chymotrypsin. The presence of the sulfide bond increased the inhibitory potency on all of the enzymes tested when compared with compounds lacking the sulfide. In general, the compounds proved to be poor inhibitors of chymotrypsin and moderate inhibitors of trypsin. By varying the substituent on the sulfide, good inhibitory activity was obtained on α-naphthyl acetate esterase, acetylcholinesterase, while some of the compounds proved to be extremely powerful inhibitors of juvenile hormone esterase. The most powerful inhibitor tested was 3-octylthio-1,1,1-trifluoro-2-propanone, with an I50 of 2.3 × 10?9M on JH esterase. This compound showed a molar refractivity similar to that of the JH II backbone, was not toxic to T. ni, and was moderately toxic to mice, with a 48-hr LD50 of >750 mg/kg. It effectively delayed pupation when applied to prewandering larvae of T. ni, as expected for a JH esterase inhibitor. Thus, some members of this series are promising for evaluating the role of JH esterase in insect development. The series also indicates that, by varying the substituent on the sulfide moiety, potent “transition-state” inhibitors can be developed for a wide variety of esterases and proteases.  相似文献   

19.
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20.
药剂对小菜蛾抗性及敏感品系乙酰胆碱酯酶抑制作用比较   总被引：5，自引：1，他引：4  
采用浸叶法测定了云南通海、元谋和澜沧的小菜蛾plutella xylostella田间种群对常用杀虫剂的抗药性。结果表明,云南上述地区小菜蛾田间种群对各类杀虫剂均产生了不同程度的抗性。对有机磷类药剂的抗药性为1.74~31.1倍;对菊酯类药剂的抗药性为7.41~764倍;对阿维菌素类药剂则产生了 5.60~4.06×104倍的抗性。通过离体和活体试验测定了药剂对小菜蛾头部乙酰胆碱酯酶(AChE)的抑制作用。敌敌畏和灭多威对通海抗性品系AChE离体和活体内的抑制中浓度(I50)分别是敏感品系的209、26.5倍和2.21、2.16倍;敌敌畏对通海小菜蛾种群的离体和活体内抑制中时间(IT50)小于敏感品系,分别是敏感品系的0.32和0.17倍;而灭多威对通海小菜蛾种群的离体和活体内抑制中时间(IT50)则大于敏感品系,分别是敏感品系的1.37和1.74倍。  相似文献   

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