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1.
Essential oils of Matricaria chamommilla, Mentha piperita, M. spicata, Lavandula angusti folia, Ocimum basilicum, Thymus vulgaris, Origanum vulgare, Salvia officinalis, Citrus limon and C. aurantium and their components; linalyl acetate, linalool, limonene, α-pinene, β-pinene, 1,8-cineole, camphor, carvacrol, thymol and menthol were assayed for inhibitory activity against the three major pathogens of the button mushroom, Agaricus bisporus, i.e. the fungi Verticillium fungicola and Trichoderma harzianum and the bacterium Pseudomonas tolaasii. The highest and broadest activity was shown by the Origanum vulgare oil. Carvacrol possessed the highest antifungal activity among the components tested.  相似文献   

2.
A series of chiral β-arylalkyl-1H-1,2,4-triazole derivatives were prepared and both their in vitro antifungal activities against Penicillium digitatum and binding activity toward CYP51 protein of P. digitatum (PdCYP51) were tested. In general, the in vitro inhibitory activities of R- and S-enantiomers were in good agreement with the corresponding binding activities in cultured cells. Furthermore, the preliminary molecular docking modeling of representative compounds are described to provide more insight into their stereoselective interaction, as well as further rationalize the observations of the activities of chiral azoles as demethylase inhibitors for defense against postharvest pathogens.  相似文献   

3.
Sphaeropsis sapinea was repeatedly isolated in Sardinia from symptomatic samples of the upper part of declining pine (Pinus radiata) plants. Observed symptoms mainly consisted of foliage chlorosis, drying of needles and cankers on branches. The S. sapinea strains were shown to produce phytotoxic metabolites in culture filtrates. Three metabolites were isolated for the first time from this fungus and identified by their spectroscopic and optical properties as R-(−)-mellein, (3R,4R)-4-hydroxymellein and (3R,4S)-4-hydroxymellein. When assayed for phytotoxic and antifungal activities on host and non-host plants and on some phytopathogenic fungi, the R-(−)-mellein showed significant activity, while the other two 3,4-dihydroisocoumarins showed only a synergic activity in both tests.  相似文献   

4.
A comparison of the uptake of simple (C1–C4) aliphatic amines byPenicillium digitatum revealed that the fungitoxicity of (?)sec-butylamine [(?)SBA] was not due to its accumulation by hyphae since (+)SBA was accumulated to the same extent and methylamine, which showed negligible antifungal activity, accumulated to twice the level of SBA. Amines with a secondary alkyl structure were resistant to fungal metabolism, whereas primary amines were degraded to a significant extent byP. digitatum during a 4 h incubation period.(?)SBA accumulated in the fresh hyphae ofP. digitatum to a level 24 times higher than that in the culture medium containing 1 μmol ml?1; most of the SBA effluxed from the hyphae when transferred to fresh culture medium minus SBA. SBA did not accumulate when hyphae were incubated in N2 or in the presence of respiratory inhibitors. The absorption and accumulation of SBA is characteristic of active transport.Penicillium species and biotypes that are sensitive to SBA did not accumulate more (?)SBA than resistant fungi. SBA-resistant biotypes ofP. digitatum accumulated SBA to twice the level of SBA-sensitive biotypes, but did not accumulate pyruvate in the hyphae, which is characteristic of SBA-altered metabolism.No evidence was found to implicate exclusion or metabolic detoxification as mechanisms of SBA resistance. More probably, resistance involves cytoplasmic sequestration of SBA or low affinity of the biochemical target, pyruvic dehydrogenase.  相似文献   

5.
The effect of essential oils and individual monoterpenoids on soil-borne fungi, in pure and mixed cultures, in growth media and in the soil environment, was investigated. Essential oils were extracted from lavender (Lavandula stoechas), oregano (Origanum vulgare subsp. hirtum), sage (Salvia fruticosa) and spearmint (Mentha spicata). The monoterpenoids tested were fenchone, carvacrol, 1,8-cineole, carvone, α-pinene and terpinen-4-ol. Their effect was examined on growth and sporulation of Aspergillus terreus, Fusarium oxysporum, Penicillium expansum and Verticillium dahliae isolated from an organic cultivation of tomato. All tested essential oils and individual monoterpenoids inhibited mycelial growth in all fungi and conidial production in most fungi. The strongest inhibitory activity on mycelial growth was exhibited by oregano and spearmint oils and by carvacrol and carvone, respectively their main constituents. The inhibitory activity was clearly fungistatic in A. terreus and F. oxysporum but fungicidal in V. dahliae. On sporulation, clearly stimulatory effects were observed alongside inhibitory ones. Conidial production was always promoted by α-pinene in P. expansum and by sage oil in F. oxysporum. At certain dosages it was promoted by cineole and carvone in F. oxysporum, and by lavender oil in A. terreus and V. dahliae. Experiments with carvone and carvacrol against mixed fungal cultures in a soil environment showed that V. dahliae was the most sensitive and A. terreus the most tolerant of the four fungi. Our results demonstrate strong but divergent effects and selectivity of action of the lower terpenoids on fungal strains that can become serious pests of tomato. Of special importance is the complete inhibition of growth and conidial production of V. dahliae, a pathogen otherwise very resistant to chemical control.  相似文献   

6.
This study evaluated the direct antifungal activity of tiadinil [N-(3-chloro-4-methylphenyl)-4-methyl-1,2,3-thiadiazole-5-carboxamide], a systemic acquired resistance (SAR) inducer and two formulations of thymol (thymol I and thymol II) against Stagonosporopsis citrulli, the causal agent of gummy stem blight (GSB) disease of watermelon. Tiadinil, thymol I and thymol II completely inhibited the mycelial growth of S. citrulli in vitro at ≥?100 ppm. Conidial germination and germ tube elongation were completely inhibited by tiadinil at ≥?2000 ppm and by thymol-based formulations at ≥?100 ppm. A single foliar application of tiadinil at ≥?10 ppm or a single application of thymol I and II at ≥?1 ppm, 48 h before or after pathogen inoculation, significantly reduced disease severity of watermelon seedlings inoculated with 105/ml conidial suspension of S. citrulli, compared to respective nontreated controls. Plants treated with foliar application of tiadinil at ≥?1000 ppm before pathogen inoculation had significantly lower disease severity than plants that received an equivalent drench application. The efficacy of foliar application of tiadinil was affected by concentration and frequency of application. The study suggests direct antifungal activity of tiadinil, indicating a new mode of action of tiadinil against GSB disease of watermelon. The study also demonstrated direct antifungal action of thymol, a formulated active compound of essential oils, against S. citrulli and GSB disease of watermelon.  相似文献   

7.
The aim of this study was to evaluate the antifungal activity of haliscosamine isolated from Haliclona viscosa sea sponge from the Moroccan Atlantic coast against Penicillium digitatum, the causal agent of citrus green mould. The in vitro antifungal activity of haliscosamine, determined using the agar disc‐diffusion method, showed that haliscosamine and DESOGERME SP VEGETAUX® (reference product) have fungicidal activity with inhibition diameters of 19 and 18 mm, respectively. Haliscosamine and a positive control (DESOGERME SP VEGETAUX®) were tested in vivo in comparison with a negative control on orange fruits in normal storage conditions. This test showed that after four weeks of storage, the rate of decay of citrus fruits treated with haliscosamine or DESOGERME does not exceed 14%, whereas in the negative control the decay rate is 77%. The results of in vitro and in vivo tests indicate that haliscosamine and DESOGERME SP VEGETAUX® have an important antifungal potential against P. digitatum and that haliscosamine (a natural product) may represent an alternative to the use of chemical fungicides.  相似文献   

8.
Metabolism of the triazolylmethane fungicides triadimefon, triadimenol, and diclobutrazol by Aspergillus niger was studied using a replacement culture technique and 14C substrates. Components of metabolite mixtures were characterized by TLC, GLC, radio-GC, and GC-MS analyses of the free materials and their trifluoroacetate and trimethylsilyl ether derivatives. The three compounds underwent a common metabolic change involving oxidation of C(CH3)3 to C(CH3)2CH2OH. In this work the isopropyl analog of triadimefon, previously reported as a metabolite, was an artifact and resulted from nonbiological oxidation of the corresponding primary alcohol. The fungus also reduced triadimefon to triadimenol, giving a mixture of 1R2S, 1S2R and 1R2R, 1S2S diastereoisomers. The less fungitoxic 1R2S, 1S2R triadimenol predominated, so that this conversion may be directly associated with the relative insensitivity of A. niger to triadimefon. Implications of oxidative and reductive metabolism of these fungicides are suggested with particular reference to the differing fungitoxicities of diastereoisomers and enantiomers.  相似文献   

9.
In a young mixed pine plantation (Pinus nigra andP. pinea) in central Italy, the influence of the pine needle monoterpenes (R)-(+)-limonene, (S)-(−)-limonene and (1S)-(−)-β-pinene on the oviposition activity of the pine processionary moth,Thaumetopoea pityocampa (Denis et Schiffermüller), was assessed. Two application methods were compared: spraying the trees with the substances emulsified with water, and setting up polyethylene dispensers from which the monoterpenes evaporated. During the moth’s flight period weekly treatments (at 500 mg of monoterpene /l water) were carried out and the evaporation from the polyethylene dispensers (each with 5 g of a single monoterpene) was checked on each occasion by weighing the dispensers. The GLM analysis did not uncover any difference between the methods of application or between the pine species.T. pityocampa laid a significantly (P=0.01) lower number of egg masses on the trees treated with (1S)-(−)-β-pinene than on those treated with the other substances and on the control trees. A ∼45% reduction in egg mass number was obtained on the pines treated with (1S)-(−)-β-pinene, independent of the level of infestation, method of application or pine species. (R)-(+)-limonene and (S)-(−)-limonene were not effective. http://www.phytoparasitica.org posting July 29, 2008.  相似文献   

10.
Commercial plant essential oils obtained from 40 plant species were tested for their antifungal activity against Phytophthora cactorum, Cryphonectria parasitica, and Fusarium circinatum. Strong antifungal activity against Phytophthora cactorum was achieved with the essential oil derived from Oriental sweetgum, Liquidambar orientalis at 28 × 10−3 mg/mL air concentration. In a test with C. parasitica, inhibition rate of patchouli was 51.0%, whereas the other essential oils showed weak activity. Essential oils of manuka (Leptospermum scoparium) and patchouli (Pagostemon patchouli) showed moderate activity against F. circinatum. Analysis by gas chromatography-mass spectrometry led to identification of 11 compounds in the oil of L. orientalis. The antifungal activity of identified compounds was tested singularly by using standard or synthesized compounds. Inhibition rates of cinnamyl aldehyde and benzaldehyde were 100% against P. cactorum at 28 × 10−3 mg/mL air concentration. There was a significant morphological alternation in three phytopathogenic fungi after oil or compound treatment.  相似文献   

11.
The efficacy of the essential oil and methanolic extracts of Erigeron ramosus (Walt.) B.S.P. was evaluated for controlling the growth of some important phytopathogenic fungi. The hydrodistilled essential oil was analysed by GC-MS. Thirty one compounds representing 95.3% of the total oil were identified, of which β-caryophyllene (24.0%), α-humulene (14.5%), 1,8-cineole (9.0%), eugenol (7.2%), globulol (7.1%), caryophyllene oxide (5.2%), δ-cadinene (5.0%), α-copaene (4.9%) and widdrol (2.0%) were the major compounds. Thus, the monoterpenes and sesquiterpenes were the predominant portions of the oil. Essential oil and methanol extract of E. ramosus and the derived fractions of hexane, chloroform and ethyl acetate were tested for anti-fungal activity, which was determined by disc diffusion and minimum inhibitory concentration (MIC) determination methods. The oil (1,000 ppm) and methanolic extracts (1,500 ppm) displayed great potential of anti-fungal activity as a mycelial growth inhibition against the tested phytopathogenic fungi such as Fusarium oxysporum (KACC 41083), Phytophthora capsici (KACC 40157), Colletotricum capsici (KACC 410978), Fusarium solani (KACC 41092), Rhizoctonia solani (KACC 40111), Sclerotinia sclerotiorum (KACC 41065) and Botrytis cinerea (KACC 40573), in the range of 49.3–70.3% and minimum inhibitory concentration ranging from 125–500 μg ml-1. The results obtained from this study may contribute to the development of new anti-fungal agents to protect the crops from fungal diseases.  相似文献   

12.
There are still no effective means to control Dutch elm disease (DED), caused by the vascular fungi Ophiostoma ulmi and O. novo-ulmi. Plant phenolics may provide a new strategy for DED control, given their known antifungal activity against pathogens and their involvement in plant defence mechanisms. The in vitro antifungal activity of salicylic acid, carvacrol, thymol, phenol, o-cresol, m-cresol, p-cresol, and 2,5-xylenol against the DED pathogens was tested. Also, the protective effect of watering Ulmus minor seedlings with these compounds was tested against O. novo-ulmi. Salicylic acid, carvacrol, and thymol showed the strongest antifungal in vitro activity, while carvacrol and salicylic acid provided the strongest in vivo protection against O. novo-ulmi (63 and 46% reduction of leaf wilting symptoms with respect to controls, respectively). The effect of the treatments on tree phenology was low, and a significant negative relation was observed between the number of days to bud burst and the leaf wilting symptoms after inoculation, probably determined by genetic differences among the elm tree progenies used. The treatments with salicylic acid, carvacrol and thymol induced the highest shift in phenolic metabolite profile with respect to control trees. The protective effect of carvacrol and salicylic acid is discussed in terms of their combined activity as antifungal compounds and as inductors of tree defence responses.  相似文献   

13.
Metalaxyl [methyl-N-(2′-methoxyacetyl)-N-(2,6-dimethylphenyl)-d,l- alaninate] is a potent phenylamide fungicide. The (−)-(R)-isomer accounts for most of the fungicidal activity. A possible stereo and/or enantioselective kinetics of metalaxyl in rabbits was investigated by intravenous injection. The concentrations of (−)-(R)- and (+)-(S)-metalaxyl in plasma, liver, and kidney tissue were determined by HPLC with a cellulose-Tris-(3,5-dimethylphenylcarbamate)-based chiral stationary phase and gas chromatography-mass spectroscopy. After intravenous administration of racemic metalaxyl (40 mg/kg), the (+)-(S)-enantiomer levels in plasma, liver, and kidney decreased more rapidly than the (−)-(R)-isomer. The area ratio of the (−)-(R)-/(+)-(S)-enantiomer under the concentration-time curve (AUC0 → ∞) in plasma after drug application was 1.62. The total plasma clearance value of the (+)-(S)-enantiomer was 1.53 and higher than that of the (−)-(R)-enantiomer. The [R]/[S] ratio in plasma was >1 for standard rac-metalaxyl at each time point. The other pharmacokinetic parameters of the enantiomers were also different. The results indicate substantial stereoselectivity in the degradation of metalaxyl enantiomers in rabbits.  相似文献   

14.
An antifungal protein E2, from the culture filtrate of the endophytic Bacillus subtilis strain EDR4 of wheat with a high activity against numerous fungal species in vitro and take-all in wheat caused by Gaeumannomyces graminis var. tritici in vivo, was purified by (NH4)2SO4 precipitation, hydrophobic-interaction chromatography, anion-exchange chromatography and polyacrylamide gel electrophoresis (PAGE). The molecular mass of the protein was about 377.0 kDa determined by gel permeation chromatography (GPC) using a Superdex 200 10/300 GL pre-packed column and the pI value of the protein detected by isoelectric focusing PAGE was 6.59. Following sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE) the antifungal protein showed a band with a molecular mass of 39.1 kDa, which suggest that the native protein consists of multi-subunits. The amino acid sequences of three peptides from the antifungal protein were obtained by using a nano-ESI-MS/MS (Q-TOF2) System. The protein isolated may be regarded as a new protein according to amino acid sequences of three peptides. The purified protein exhibited inhibitory activity on mycelium growth of e.g. Fusarium graminearum, Macrophoma kuwatsukai, Rhizoctonia cerealis, Fusarium oxysporum f.sp. vasinfectum, Botrytis cinerea and G. graminis var. tritici (Ggt). Scanning electron microscopy showed that hyphae of Ggt treated with the antifungal protein were severely deformed. The antifungal protein E2 exhibited ribonuclease and hemagglutinating activities as well as a trifle protease activity. However, no β-1,3-glucanase, β-1,4-glucanase, chitinase or protease inhibitory activities were detected.  相似文献   

15.
Essential oils extracted fromEucalyptus blakelyi (1,8-cineole, 77.5%),Melaleuca fulgens (1,8-cineole, 56.9%) and 1,8-cineole were shown to have fumigant toxicity against different development stages ofSitophilus oryzae. The eggs ofS. oryzae were the most tolerant, followed by pupae, larvae and adults in that order.M. fulgens oil,E. blakelyi oil and 1,8-cineole at 100 μl per liter of air gave, respectively, LT50 values of 16.2, 17.4 and 9.1 h for adults, 31.1, 19.3 and 17.5 h for larvae, 55.6, 75.2 and 39.7 h for pupae, and required >7 days for eggs. Only 1,8-cineole (200 μl −1 air) gave a significant egg kill by 7 days and the LT95 was 134.5 h. 1,8-Cineole could be a useful new fumigant. http://www.phytoparasitica.org posting Oct. 3, 2004.  相似文献   

16.
17.
Rice blast is a devastating fungal disease resulting in major losses to rice crops. Owing to continuous acquisition of resistance by the causal fungus, several fungicide chemicals are no longer effective. Therefore, there is a need to identify natural components and develop new agents to control fungal pathogens. We previously demonstrated that the culture filtrate of Biscogniauxia sp. O821 inhibited infection behavior of Magnaporthe oryzae and subsequent blast lesion formation. In the present study, we isolated a new compound, (3aS,4aR,8aS,9aR)-3a-hydroxy-8a-methyl-3,5-dimethylenedecahydronaphto[2,3-b]furan-2(3H)-one (HDFO), from the culture filtrate of Biscogniauxia sp. O821 and determined its molecular weight as 248. The HDFO structure was determined by electrospray ionization-mass spectrometry and nuclear magnetic resonance spectroscopy after purification with column chromatography and high-performance liquid chromatography. The structure of this antifungal compound was similar to that of alantolactone and isoalantolactone. The growth inhibition zone against M. oryzae in presence of HDFO was observed at Rf 0.5–0.6 on a thin layer chromatography plate. HDFO inhibited conidial germination of M. oryzae in a dose-dependent manner (1–200 ppm). Furthermore, blast lesion formation was significantly suppressed by HDFO at over 5 ppm. These results suggest that HDFO from the culture filtrate of Biscogniauxia sp. O821 can protect rice from rice blast disease caused by M. oryzae. This is the first report that HDFO produced by Biscogniauxia sp. can serve as an antifungal compound against M. oryzae.  相似文献   

18.
Various isomeric mixtures of pyrethroids were examined in topical application tests against houseflies, Musca domestica. On the basis of the activities of the separate isomers of 5-benzyl-3-furylmethyl (±)-cis,trans-chrysanthemate, it was shown that when combined in pairs to give the (±)-trans or (±)-cis or (+)-cis,trans mixtures the observed mortalities did not differ from those expected by simple additive action calculated by the harmonic mean. In contrast the (±)-cis,trans mixture showed considerable antagonism with a mortality only 60% of that expected. Similar evaluations using the separate and combined isomers of bioallethrin [(R,S)-3-allyl-2-methyl-4-oxocyclopent-2-enyl (allethronyl) ( + )-trans-[(1R,3R)-chrysanthemate] and the corresponding (+)-cis-(1R,3S)-chrysanthemate indicate antagonism calculated to be correlated with the content of the (R)-isomer of the alcoholic moiety. Hence the activity of the most active isomer of the “allethrin” series, (S)-3-allyl-2-methyl-4-oxocyclopent-2-enyl ( + )-trans-(1R,3R)-chrysanthemate, (S)-bioallethrin, is not fully realised unless it is present in pure form and a substantial part of the value of bioresmethrin (5-benzyl-3-furylmethyl ( + )-trans-chrysanthemate] as a killing agent is lost when the racemic form is used. In racemic mixtures there is mutual antagonism between pairs of isomers so that considerable masking of activity occurs.  相似文献   

19.
Conversion of chrysanthemates to their cyclopropane, episulfide, and epoxide derivatives by addition of methylene, sulfur, or oxygen, respectively, to the 2-methyl-1-propenyl double bond yields products generally of reduced toxicity but enhanced neurophysiological activity and photostability. The reduced toxicity is established with cis-cyphenothrin derivatives administered intracerebrally to mice and topically to house flies and with cis-phenothrin derivatives applied topically to American cockroaches and house flies, even in the presence of piperonyl butoxide for the house flies. In contrast, cyclopropane, episulfide, and epoxide derivatives of phenothrin are more potent than the parent compound in eliciting repetitive firing following stimulation of a cercal sensory nerve of the American cockroach in vitro. The individual 1′R and 1′S isomers of epoxides derived from (1R,cisS)cyphenothrin, (1R,cis)phenothrin, and (1R,trans)tetramethrin differ in potency by up to 20-fold for insecticidal activity, >30-fold for intracerebral toxicity to mice, and ~100,000-fold in the cercal sensory nerve assay. In each case the epoxide isomer of higher Rf is more potent than that of lower Rf when derived from a trans-chrysanthemate and vice versa from a cis-chrysanthemate.  相似文献   

20.
海洋放线菌A3202的分离鉴定及其对柑橘采后病害的防效   总被引:1,自引:1,他引:0  
为获得用于防治柑橘采后病害的海洋放线菌,以柑橘青霉病菌Penicillium italicum、柑橘绿霉病菌P.digitatum和柑橘炭疽病菌Colletotrichum gloeosporioides为指示菌,对分离到的25株海洋放线菌进行筛选。通过平板对峙法测定拮抗菌株的抑菌谱,并测定其发酵产物粗提物对柑橘果实采后病害的防效,根据形态特征、培养特征、生理生化特征及16S rDNA序列对其进行鉴定。结果表明,分离自鳞笠藤壶Tetraclita squamosa的菌株A3202对3种指示菌均具有强抑菌活性,对供试13种植物病原菌的菌丝生长具有不同程度的抑制作用,尤其对柑橘青霉病菌和柑橘绿霉病菌的抑制作用最强,抑菌带宽度分别可达2.33±0.05 cm和2.32±0.10 cm。该菌株800 mg/L粗提物溶液对接种后7 d的柑橘青霉病、柑橘绿霉病和柑橘炭疽病的相对防效均可达100%。初步鉴定该菌株为放线菌中的米修链霉菌Streptomyces misionensis。  相似文献   

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