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1.
The ability to stimulate N-acetylglucosamine (GluNAc) incorporation in-vitro of a number of N-tert-butyl-N,N′-dibenzoylhydrazines having various substituents on both phenyl rings was measured in cultured integument excised from the rice stem borer (Chilo suppressalis Walker). The relationship between in-vitro and larvicidal potency was approximately linear. The substituent effects on variations in the potency were similar between in-vitro and larvicidal activities. An inhibitor of oxidative detoxication, piperonyl butoxide, had no synergistic effects on the in-vitro potency. The ability of some dibenzoylhydrazines to inhibit GluNAc incorporation at exposure periods longer than the optimum for stimulation was also measured in a similar cultured integument system. The relationship between the inhibitory and stimulatory potency indices was linear, indicating that the larvicidal activity of dibenzoylhydrazines is closely related to its ability to stimulate as well as to inhibit GluNAc incorporation into the larval cuticle.  相似文献   

2.
Twenty trifluoromethylphenyl amides were synthesized and evaluated as fungicides and as mosquito toxicants and repellents. Against Aedes aegypti larvae, N-(2,6-dichloro-4-(trifluoromethyl)phenyl)-3,5-dinitrobenzamide (1e) was the most toxic compound (24 h LC50 1940 nM), while against adults N-(2,6-dichloro-4-(trifluoromethyl)phenyl)-2,2,2-trifluoroacetamide (1c) was most active (24 h LD50 19.182 nM, 0.5 μL/insect). However, the 24 h LC50 and LD50 values of fipronil against Ae. aegypti larvae and adults were significantly lower: 13.55 nM and 0.787 × 10−4 nM, respectively. Compound 1c was also active against Drosophila melanogaster adults with 24 h LC50 values of 5.6 and 4.9 μg/cm2 for the Oregon-R and 1675 strains, respectively. Fipronil had LC50 values of 0.004 and 0.017 μg/cm2 against the two strains of D. melanogaster, respectively. In repellency bioassays against female Ae. aegypti, 2,2,2-trifluoro-N-(2-(trifluoromethyl)phenyl)acetamide (4c) had the highest repellent potency with a minimum effective dosage (MED) of 0.039 μmol/cm2 compared to DEET (MED of 0.091 μmol/cm2). Compound N-(2-(trifluoromethyl)phenyl)hexanamide (4a) had an MED of 0.091 μmol/cm2 which was comparable to DEET. Compound 4c was the most potent fungicide against Phomopsis obscurans. Several trends were discerned between the structural configuration of these molecules and the effect of structural changes on toxicity and repellency. Para- or meta- trifluoromethylphenyl amides with an aromatic ring attached to the carbonyl carbon showed higher toxicity against Ae. aegypti larvae, than ortho- trifluoromethylphenyl amides. Ortho- trifluoromethylphenyl amides with trifluoromethyl or alkyl group attached to the carbonyl carbon produced higher repellent activity against female Ae. aegypti and Anopheles albimanus than meta- or para- trifluoromethylphenyl amides. The presence of 2,6-dichloro- substitution on the phenyl ring of the amide had an influence on larvicidal and repellent activity of para- trifluoromethylphenyl amides.  相似文献   

3.
New types of juvenogens, which are biochemically activated juvenoid esters, have been assayed for juvenile hormone activity in three species of insects. The hormonally active component, liberated from the juvenogen substrate by carboxylesterase enzymes within the insect's body, was a secondary juvenoid alcohol related to the well-known group of juvenile hormone analogs derived from 4-substituted (7-alkoxygeranyloxy)benzenes. Juvenogen esters obtained by acylation of this juvenoid alcohol with a homologous series of C2 to C18 straight-chain monocarboxylic acids retain the juvenile hormone activity of the parental alcohol. The corresponding formyl derivative, as a first member of the series, was inactive and the activity of esters with longer acyl radicals than C18 also successively diminished. Such a weak dependence for juvenile hormone activity on the size of the molecule has not previously been encountered in juvenoid esters which do not yield biologically active hydrolysis products. These findings favor an assumption that juvenogens may represent selective, nontoxic, hormonally acting pesticides whose physicochemical properties (volatility, lipophility, stability) can be adjusted to suit practical requirements by simple alterations of the biologically unimportant acyl component. Moreover, this can be done without affecting the species-specific properties in the juvenile hormone activity of the built-in juvenoid product.  相似文献   

4.
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   

5.
The influence of structural variations in compounds of the N-acylalanine type, on their fungicidal activity towards Peronosporales, was examined. Within a series of methyl N-(acyl)-N-(2,6-xylyl)alaninates ( I ), a quantitative structure-activity relationship was given for the curative action against Plasmopara viticola, through a Hansch-type equation. A deviation from this equation is discussed with reference to benalaxyl ( I ; acyl=phenylacetyl). Syntheses and qualitative indications of activity are reported for structural changes in the xylyl and in the alanine moieties. Progress in the latter approach is briefly outlined.  相似文献   

6.
The larvicidal activity of a series of N-2,6-difluorobenzoyl-N′-[4-(substituted benzyloxy)-phenyl]-ureas against nondiapause larvae of the rice stem borer, Chilo suppressalis Walker, was measured by a topical application method under conditions in which oxidative metabolism was inhibited by piperonyl butoxide. The effects of the substituted-benzyloxy moiety on variations in the activity were analyzed quantitatively using physicochemical substituent parameters and regression analysis. Results were compared with those found previously for N-2,6-difluorobenzoyl-N′-(4-substituted phenyl)-ureas, indicating that the electron-withdrawing property of the anilide substituents participates in determining the activity through the inductive effect. The hydrophobicity of the total anilide substituents favors activity, whereas the steric dimension in terms of the width lowers it. Although inhibition of new cuticle formation on cultured integument of diapausing larva could not be determined accurately for most of the compounds because of their limited solubility in the assay medium, inhibitory activity seemed related to larvicidal activity, as was the case for previously investigated simpler congeners.  相似文献   

7.
Tetrahydroquinolines (THQs), a class of nonsteroidal ecdysone agonists, are good candidates for novel mosquito control agents because they specifically bind to mosquito ecdysone receptors (EcRs). We have recently performed quantitative structure–activity relationship (QSAR) analyses of THQs to elucidate the physicochemical properties important for the ligand–receptor interaction. Based on previous QSAR results, here, we newly synthesized 15 THQ analogs with a heteroaryl group at the acyl moiety and evaluated their binding affinity against Aedes albopictus EcRs. We also measured the larvicidal activity of the combined set of previously and newly synthesized compounds against A. albopictus to examine the contribution of receptor-binding to larvicidal activity. Multiple regression analyses showed that the binding affinity and the molecular hydrophobicity of THQs are the key determinants of their larvicidal activity.  相似文献   

8.
N‐(4‐phenoxyphenyl)‐2‐pyridinecarboxamide (1) was synthesized from commercially available materials and its ovicidal and larvicidal activity against Cydia pomonella (L) was tested. The compound showed a LC50 of 0.98 mg ml−1 when eggs less than 24 h were sprayed using a Potter Tower, but it had no effect when eggs older than this were sprayed. The compound did not have larvicidal activity when larvae were treated with 1200 µg g−1. However, the larval head capsules were smaller than those in the controls when treated at this concentration. To assess its possible juvenile‐hormone‐like activity, the compound was topically applied to young pupae of Tribolium confusum duVal, where it produced clear juvenilization effects, which were dependent on the applied dose. © 2000 Society of Chemical Industry  相似文献   

9.
采用浸虫法、夹毒叶片法和叶碟法分别测定了13个含酰腙结构的新型吡唑酰胺衍生物对小菜蛾3龄幼虫的触杀、胃毒和拒食活性。结果表明:该类化合物对小菜蛾3龄幼虫具有较高的胃毒和拒食活性,其中苯环上含有氯原子、且酰腙一端的取代基含有杂原子且体积较小的化合物 H7的胃毒和拒食活性最好,明显高于对照药剂毒死蜱。H7 72 h胃毒作用LC50值为0.6 mg/L(毒死蜱的LC50值为7.4 mg/L);有10个化合物的拒食活性高于毒死蜱,其中 H7 48 h的拒食中浓度(AFC50) 最低,为0.6 mg/L,明显低于毒死蜱(AFC50=6.5 mg/L)。供试化合物对小菜蛾3龄幼虫均无触杀活性。  相似文献   

10.
BACKGROUND: Dengue fever is a severe public health problem for several countries. In order to find effective larvicides to aid control programs, the structure‐activity relationships of eugenol derivatives against Aedes aegypti (Diptera: Culicidae) larvae were evaluated. Additionally, the composition and larvicidal activity of Syzygium aromaticum essential oil was assessed. RESULTS: Four compounds representing 99.05% of S. aromaticum essential oil have been identified. The essential oil was active against Ae. aegypti larvae (LC50 = 62.3 and 77.0 ppm, field‐collected and Rockefeller larvae respectively). The larvicidal activity of eugenol, the major compound of the essential oil, was further evaluated (LC50 = 93.3 and 71.9 ppm, field‐collected and Rockefeller larvae respectively). The larvicidal activity and structure‐activity relationships of synthetic derivatives of eugenol were also assessed. The larvicidal activity of the derivatives varied between 62.3 and 1614.9 ppm. Oxidation of eugenol allylic bond to a primary alcohol and removal of the phenolic proton resulted in decreased potency. However, oxidation of the same double bond in 1‐benzoate‐2‐methoxy‐4‐(2‐propen‐1‐yl)‐phenol resulted in increased potency. CONCLUSION: Structural characteristics were identified that may contribute to the understanding of the larvicidal activity of phenylpropanoids. The present approach may help future work in the search for larvicidal compounds. Copyright © 2012 Society of Chemical Industry  相似文献   

11.
Metconazole, (1RS, 5RS; 1RS, 5SR)-5-(4-chlorobenzyl)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, is a highly active fungicide, in particular controlling seed-borne and foliar diseases of cereals, such as wheat (Triticum aestivum L.) and barley (Hordeum vulgare L.). In order to maximize its foliar activity, an experimental survey of some types of surfactants and an emulsifiable oil was undertaken. Two types of metconazole formulation were investigated using a biological assay involving the therapeutic control of two diseases (Erysiphe graminis DC f. sp. tritici Marchal and Leptosphaeria nodorum Muell.) of wheat. Enhancements of activity by ?Genapol’? C12/C14 alcohol ethoxylates of an emulsifiable concentrate (ECM) formulation of metconazole were approximately three- to four-fold. For its, initially, less active suspension concentrate (SCM) formulation, enhancements were around 35-fold, so that with these adjuvants the two formulations were of similar activity. The enhancement ability of these ?Genapol’? surfactants was optimal at lower (5–10 moles) ethylene oxide content. These analogues induced marginally better enhancements of activity than members of a range of nonylphenol ethoxylates (?Arkopal’?), and emulsifiable paraffinic/naphthenic oil (HVI 60E) and a castor oil ethoxylate (?Atlas’? G1281) but were equivalent to a similar series of alcohol ethoxylates (?Dobanol’?) from another source. Varying the alkyl chain length between C9-C11 and C14-C15 in the ?Dobanol’? series had little effect on their high enhancements of metconazole activity. It was determined from trials varying the application rate of the best alcohol ethoxylates that application rates of 1–1.5 kg ha?1 were required for maximum activity. This implied the use of high adjuvant/metconazole ratios in one-pack adjuvant-containing formulations. A range of soluble liquid (SL) formulations were prepared with either ?Dobanol’? 23–6.5 or ?Dobanol’? 91-6/metconazole ratios varying from 5:1 to 15:1. There were found to be highly active and were recommended for field testing.  相似文献   

12.
Non-cyclopropane pyrethroid esters of different substituted 2-phenoxy-3-methylbutanoic acids have been synthesised using the three alcohols—3-phenoxybenzyl alcohol, α-cyano-3-phenoxybenzyl alcohol and 3, 4-methylene-dioxybenzyl alcohol. Among the 35 esters synthesised and tested against Culex quinquefasciatus Say, the Bancroftian filariasis vector, for both larvicidal and adulticidal activities, α-cyano-3-phenoxybenzyl 2-(4-fluorophenoxy)-3-methylbu-tanoate, with an LC50 value of 2.5 × 10?3 mg litre?1 for larvicidal activity, and α-cyano-3-phenoxybenzyl-2-(4-chlorophenoxy)-3-methylbutanoate, with an LD50 value of 30 times; 10?4 ug insect?1 for adulticidal activity, were found to be as effective as fenvalerate, a well-known non-cyclopropane pyrethroid ester. Structure-activity studies showed that the insecticidal activity is dependent on the nature and position of the substituent in the phenyl ring of the acid moiety and also on the type of alcohol moiety.  相似文献   

13.
3-Methyl-5-(acyl/alkyl)aminoisoxazole-4-thiocyanates were prepared by rhodanation of N-acyl/alkyl-3-methyl-5-isoxazolamines. These products were tested for antifungal activity against a series of phytopathogenic fungi of different taxonomic classes. Some of the compounds showed interesting in-vitro activity. The more active compound in the in-vitro test displayed a moderate preventive activity against Plasmopara viticola, Alternaria solani and Pyricularia recondita.  相似文献   

14.
BACKGROUND: Phthalic acid diamide derivatives are among the most important classes of synthetic insecticides. In this study, a 3,3‐dichloro‐2‐propenyloxy group, the essential active group of pyridalyl derivatives, was incorporated into phthalic acid diamide derivatives with the aim of combining the active groups to generate more potent insecticides. RESULTS: Thirty‐one new phthalic acid diamides were obtained, and these were characterised by 1H and 13C NMR. The structure of N2‐[1,1‐dimethyl‐2‐(methoxy)ethyl]‐3‐iodo‐N1‐[4‐(3,3‐dichloro‐2‐propenyloxy)‐3‐(trifluoromethyl)phenyl]‐1,2‐benzenedicarboxamide was determined by X‐ray diffraction crystallography. The insecticidal activities of the compounds against Plutella xylostella were evaluated. The title compounds exhibited excellent larvicidal activities against P. xylostella. Structure‐activity relationships revealed that varying the combination of aliphatic amide and aromatic amide moieties, or the nature and position of substituent Y on the aniline ring, could aid the design of structures with superior performance. CONCLUSION: A series of novel phthalic acid diamides containing a 3,3‐dichloro‐2‐propenyloxy group at the 4‐position of the aniline ring were designed and synthesised. Structure‐activity relationships with the parent structure provided information that could direct further investigation on structure modification. Copyright © 2012 Society of Chemical Industry  相似文献   

15.
More than 20 N-(2-cyano-2-methoximinoacetyl)amino acids and derivatives were synthesised and tested for antifungal activity against grape downy mildew, caused by Plasmopara viticola (de Bary) Berl. & de Toni, and rape downy mildew, Peronospora parasitica Fr. Two of the compounds containing a free carboxylic acid group, a moiety which has been shown to confer phloem mobility on compounds, showed high activity, especially against P. parasitica, in protectant tests. These results indicate that there is no incompatibility between the acid function and fungicidal activity. A number of the esters showed activity comparable with that of cymoxanil in the protectant tests, and the tert-butyl esters of the methionine derivative and its sulfone were more than ten times as active as the commercial compound.  相似文献   

16.
Substrate specificity has been widely studied in vertebrate cholinesterases and it has been shown that two phenylalanines in the acyl pocket of acetylcholinesterase govern the acceptance of the acetyl/butyryl moiety of the choline esters. As an insecticide‐resistance mutation has been evidenced in the acyl pocket of Drosophila melanogaster and Musca domestica acetylcholinesterase we investigated the possibility of linking changes in acetyl/butyrylthiocholine specificity with mutations in insect acetylcholinesterase. We thus analyzed the effect of 28 mutations in Drosophila enzyme on acetyl/butyrylthiocholine, N‐methyl/N‐propyl‐carbamates and ethyl/methyl‐paraoxon preference. It appeared that the highest changes on acetyl/butyrylthiocholine and N‐propyl/N‐methyl‐carbamates preference were due to mutations in the acyl pocket. Nevertheless, other insecticide‐resistance mutations, not located in the acyl pocket, also modified these substrate preferences. Moreover, the effect of mutations in the acyl pocket was hidden when some other insecticide‐resistance mutations were combined in the enzyme. Consequently, acetyl/butyrylthiocholine preference alteration cannot be used as a marker to localize a mutation in the insect AChE. © 2000 Society of Chemical Industry  相似文献   

17.
The paper describes the biophore models of sulfonylurea, imidazolinone, triazolopyrimidinesulfonamide and 5‐pyrimidyltriazolo‐3‐sulfonamides established by the Apex‐3D method. A series of N‐phenylsulfonyl‐N ′‐(thiadiazol‐2‐yl)oxamides and three types of triazolopyrimidinesulfonamide were synthesised and their herbicidal activities determined to assess the validity of the model. In general, the model gave useful leads to activity, although the actual level was not always predicted accurately. In only a few cases did compounds predicted as being active prove to be inactive in the bioassay, and compounds with little or no activity were clearly indicated. As a result of this work, the compound N,N ′‐[1‐(5,7‐dimethyl‐1,2,4‐triazolo[1,5‐a]pyrimidin‐2‐yl‐thio)butane‐2,3‐di‐imino]bis(2‐chlorobenzenesulfonamide) was selected as showing good activity against a range of species, and will be used as a lead for further development. © 2000 Society of Chemical Industry  相似文献   

18.
A series of amides and esters of substituted benzo[b]furan-2-carboxylic acids have been synthesised, and their activity against adult sweet potato weevils, Cylas formicarius elegantulus (Summer) studied. The topical insecticidal potency of these compounds was compared in acetone solution and in a mixture of piperonyl butoxide (PB) and acetone (0·05+99·95 by volume). The compounds were much more active when administered in the acetone/PB mixture, and exhibited 48-h LD50 values ranging from 1·7 to 26·6 μg per insect. The most active compound, 2-(3,5-dimethylpyrazol-1-ylcarbonyl)-6-methoxy-3-methylbenzofuran, was equiactive with technical grade dimethoate (in acetone/PB) on a weight basis. © 1998 SCI  相似文献   

19.
BACKGROUND: Myracrodruon urundeuva Fr. Allemao is a common tree in the Caatinga that has been widely used for various medical purposes. Previous studies showed that the ethanol seed extract of M. urundeuva has potent activity against the larval stage of the dengue vector Aedes aegypti. Given this potential insecticidal activity, bioguided separation steps were performed in order to isolate the active compound(s). RESULTS: The isolation process resulted in only one active chemical compound, identified by infrared spectroscopy and mass spectrometry as m-pentadecadienyl-phenol. This compound presented potent larvicidal and pupicidal activity (LC50 10.16 and 99.06 µg mL−1 respectively) and great egg hatching inhibitory activity (IC50 49.79 µg mL−1). The mode of action was investigated through observations of behavioural and morphological changes performed in third-instar larvae treated with m-pentadecadienyl-phenol solution after 1, 6, 12, 16 and 20 h of exposure. Some changes were observed as flooding of the tracheal system, alterations in siphonal valves and anal gills and lethargy, probably caused by the strong anticholinesterasic activity reported previously. CONCLUSION: The compound isolated from M. urundeuva seeds, m-pentadecadienyl-phenol, showed potent activity against immature stages of dengue vector, Ae. aegypti, being considered the main larvicidal principle. Copyright © 2012 Society of Chemical Industry  相似文献   

20.
The entire genome of bacteriophage OP1, lytic for Xanthomonas oryzae pv. oryzae causing bacterial leaf blight of rice, and the partial genomes of related phages were sequenced and analyzed. The OP1 genome comprises double-stranded, 4785-bp long DNA with 51.1% G + C content. Fifty-nine open reading frames (ORFs) were detected. ORF25 had similarity with the tail fiber gene of phages, whose product is related to host specificity. The ORF25 regions were amplified from four host-range mutants (OP1h, OP1hC, OP1h2, and OP1h2C) by polymerase chain reaction, and their deduced amino acid sequences were compared. Three mutants (OP1hC, OP1h2, OP1h2C) had duplications of a small domain in the N-terminal portion, although there were slight differences in the position of the duplicated sequences. One mutant OP1h had substituted amino acids in the duplication region. New mutants isolated in the laboratory (OP1hC and OP1h2C from OP1 and OP1h2) acquired the ability to lyse strain N5874 belonging to phagovar (lysotype) C. However, they rapidly lost this lytic ability when incubated with other phagovars. This loss was always accompanied by a loss of the characteristic repeats, suggesting that the host range of OP1-related phages changed mainly through duplication and deletion of a small domain in ORF25. The nucleotide sequence data reported are available in the DDBJ/EMBL/GenBank databases under the accession numbers AP008979, AB214312 to AB214316  相似文献   

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