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以曲酸为原料,设计合成了16个曲酸衍生物(QI-01~QI-16)和10个氯曲酸衍生物(QII-01~QII-10),通过核磁共振氢谱及元素分析对其结构进行了表征。初步抑菌活性测定结果表明:所有供试化合物对苹果炭疽病菌Glomerella cingulata和番茄灰霉病菌Botrytis cinerea的菌丝生长均有不同程度的抑制作用,其中化合物QI-07和QI-11对苹果炭疽病菌活性最高,50μg/mL时的抑制率分别为79.3%和86.2%;化合物QII-04、QII-08和QII-09对番茄灰霉病菌活性最高,50μg/mL时的抑制率分别为70.0%、70.0%和76.7%。 相似文献
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An antagonistic Streptomyces strain B28, isolated from the soil collected in Tianmu mountain of Zhejiang Province, was identified as Streptomyces diastatochromogenes by morphological , physiological & biochemical characteristics and 16S rDNA sequence alignment. Antagonistic study indicated that its secondary metabolite toyocamycin had an antifungal activity on the mycelial growth of seven species of plant pathogenic fungi. The results showed that toyocamycin possessed marked inhibitory activity against Rhizoctonia solani and the EC50 value was 0. 58 μg / mL. The effective of toyocamycin against Botrytis cinerea and Fusarium oxysporum f. sp. cucumerinum was much higher than that against Colletotrichum gloeosporioides, the EC50 value oftoyocamycin in inhibiting B. cinerea, F. oxysporum and C. gloeosporioides were 13. 65 μg / mL, 12. 33 μg / mL, and 30. 15 μg / mL respectively. 相似文献
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The bacterial strain GC-B26, which showed strong antifungal and anti-oomycete activity against some plant pathogens, was isolated from a grassland soil in Korea. Based on morphological, physiological and biochemical characteristics, GC-B26 was identical to Pseudomonas aeruginosa (Schroeter) Migula. The antibiotic G26A, active against Phytophthora capsici Leonian and Colletotrichum orbiculare (Berk & Mont) van Arx, was isolated from the culture filtrates of Ps aeruginosa strain GC-B26 using various chromatographic procedures. The EI mass and UV spectral results indicated that G26A is an analogue of phenazines, having molecular formula C13H8N2O2 (M+, m/z 224.0664). On the basis of NMR spectral data, G26A was confirmed as phenazine-1-carboxylic acid. C orbiculare, P capsici and Pythium ultimum Trow were most sensitive to G26A, with MIC values of approximately 5 microg ml(-1). However, no antimicrobial activity was found against yeasts and bacteria, even at a concentration of over 100 microg ml(-1). Treatment with the antibiotic gave highly significant protective activity against the development of Phytophthora disease on pepper and anthracnose on cucumber plants. The disease control efficacy was only slightly less than that of the commercial fungicides metalaxyl and chlorothalonil. 相似文献
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苯甲酸对植物病原菌的离体抗菌活性研究 总被引：1，自引：0，他引：1
苯甲酸对植物病原菌的活性受pH值影响较大,通常在酸性条件下的活性较高。在pH=5条件下,苯甲酸对供试的8种植物病原真菌表现出不同程度的抑制活性,其中对黄瓜疫霉病菌和水稻纹枯病菌的活性相对较高,EC50分别为24.40μg/mL和62.65μg/mL,其次是水稻稻瘟病和番茄灰霉病菌,而对小麦赤霉病菌及苹果斑点落叶病菌的活性相对较差,对辣椒炭疽病菌和苹果腐烂病菌基本无活性;苯甲酸对稻瘟病菌的菌丝干重增加、孢子萌发和芽管伸长均有较高的抑制活性,但对产孢量无影响。 相似文献
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Daoubi M Durán-Patrón R Hmamouchi M Hernández-Galán R Benharref A Collado IG 《Pest management science》2004,60(9):927-932
An efficient, one-pot synthesis of angular and linear dihydropyranocoumarins, along with C-6 and C-8 prenylated coumarins is reported. These compounds, together with single- and furanocoumarins, were tested for their potential antifungal activity against the phytopathogen Botrytis cinerea Pers ex Fr. The results show that furanocoumarins may be able to control the fungus B cinerea. 相似文献
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The glycolipid antibiotic rhamnolipid B isolated from Pseudomonas aeruginosa strain B5 was evaluated for in vitro antifungal activity and in vivo control against phytophthora blight and anthracnose under glasshouse conditions. Rhamnolipid B showed antifungal activity against Cercospora kikuchii, Cladosporium cucumerinum, Colletotrichum orbiculare, Cylindrocarpon destructans, Magnaporthe grisea and Phytophthora capsici. Microscopic observation revealed that the high level of antifungal activity (10 µg ml −1) against P capsici was mainly due to a lytic effect on zoospores. Zoospore lysis began in the presence of 10 µg ml −1 of rhamnolipid B and most of the zoospores were collapsed at 25 µg ml −1. Rhamnolipid B showed inhibitory activity against the germination of zoospores and hyphal growth of P capsici at concentrations of 50 µg ml −1. Spore germination of the anthracnose plant pathogen C orbiculare was also inhibited in the presence of 50 µg ml −1 of rhamnolipid B, although hyphal growth was not affected at this concentration. In the glasshouse, the efficacy of rhamnolipid B against phytophthora blight was similar to that of metalaxyl on pepper plants when treated just before inoculation with P capsici. Treatment with either at 500 µg ml −1 completely protected pepper plants from phytophthora blight. Rhamnolipid B also suppressed the development of C orbiculare infection on leaves of cucumber plants. © 2000 Society of Chemical Industry 相似文献
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M. O. Leyva B. Vicedo I. Finiti V. Flors G. Del Amo M. D. Real P. García‐Agustín C. González‐Bosch 《Plant pathology》2008,57(6):1038-1046
The antifungal activity of hexanoic acid on the phytopathogen Botrytis cinerea was studied. This chemical inhibited both spore germination and mycelial growth in vitro in a concentration‐ and pH‐dependent manner, and stopped spore germination at a very early stage, preventing germ‐tube development. The minimum fungicidal concentration (MFC) for in vitro spore germination was 16 mm . Hexanoic acid also inhibited in vitro mycelial growth of germinated spores at an MFC of 12 mm . Studies performed to characterize the mechanisms underlying the antimicrobial effect of hexanoic acid showed that it alters fungal membrane permeability. In addition, hexanoic acid treatment increased the levels of spermine, spermidine, putrescine and cadaverine in B. cinerea mycelia. Spray application of hexanoic acid at fungicidal concentrations on 4‐week‐old tomato plants prior to fungal inoculation reduced necrosis diameter by approximately 60%. Application of the same hexanoic acid concentrations on previously infected plants reduced further necrosis expansion by around 30%. The results suggest that this chemical acts as a preventive and curative fungicide. Interestingly, treatments with hexanoic acid at concentrations below the MFC in hydroponic solution prior to fungal inoculation significantly reduced necrosis area. These results suggest an inducer effect of plant responses for hexanoic acid treatments at these concentrations. Hexanoic acid is a good candidate for safe antifungal treatments for the control of B. cinerea, which is responsible for many economic losses on fruits, vegetables and flowers. 相似文献
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Four novel 5-acyloxyimino-5-deoxyavermectin B1 compounds have been synthesized from avermectin B1 by selective oxidization of the hydroxy group at C-5, followed by oximation and convenient esterification. Their structures were confirmed by IR, 1H NMR, 13C NMR and MS. Insecticidal activities of the intermediate oxime and the four new acyl derivatives were evaluated against Helicoverpa armigera, Spodoptera exigua and Musca domestica. 相似文献
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Castelo-Branco PA Rubinger MM Guilardi S Leite VM dos Santos AR de C Alves L Lariucci C Vencato I Piló-Veloso D Zambolim L 《Pest management science》2009,65(1):34-40
BACKGROUND: Avenaciolide, a natural product isolated from Aspergillus avenaceus H. Smith, possesses several interesting biological properties, such as antifungal and antibacterial activities and inhibition of glutamate transport in mitochondria. In a study aiming to discover new compounds with antifungal activity, a bis‐γ‐lactone analogous to avenaciolide was prepared and characterized by elemental analysis, mass spectrometry, and infrared and NMR spectroscopy. RESULTS: The absolute structures of this compound and of the synthetic precursor (also a bis‐γ‐lactone) were determined by X‐ray diffraction analysis. The bis‐γ‐lactones synthesized crystallize in the orthorhombic space group P212121, and the crystal packings are supported by C? H···O hydrogen bonds. The compound showed antifungal activity against Colletotrichum gloeosporioides (Penz.) Penz. & Sacc., while the synthetic precursor was inactive under the in vitro test conditions employed. CONCLUSION: The results indicate that it is not only the bis‐γ‐lactone skeleton that is important to antifungal activity. The latter also depends on the presence of the exocyclic double bond possibly due to a Michael addition type reaction with the fungal enzymes. Copyright © 2008 Society of Chemical Industry 相似文献
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BACKGROUND: Structure–activity relationships are often reported in scientific studies. These may be employed in searching for new acceptable biocides to use against harmful microorganisms, because the biocides used hitherto encounter various problems, including lack of efficiency, high toxicity and persistence. Nowadays, scientists are trying to find new, environmentally acceptable biocides to replace these earlier biocides. Different compounds from renewable materials have been studied and have shown pronounced antifungal activity against wood fungi. These include aminopolysaccharide derivatives and different quaternary ammonium polymers. A biological study carried out with these products indicated a possible relationship between amino groups and differences in biological activity observed. RESULTS: In this study, an amino group was successively fixed to different carbon atoms of glucose, and glucosamine was also modified by both N‐alkylation and quaternisation. The impact of the amino group position on antifungal activity against two wood decay fungi was investigated. The amino group at the anomeric position showed the highest antifungal activity against both Coriolus versicolor Quel. and Poria placenta (Fr.) Cooke. Furthermore, the positive impact of both N‐alkylation and quaternisation on the growth of both strains was demonstrated. CONCLUSION: The anomeric position of the amino group and the N‐alkylation and quaternisation of amino sugars considerably increase the antifungal activity of these compounds. Copyright © 2010 Society of Chemical Industry 相似文献
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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
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Almada-Ruiz E Martínez-Téllez MA Hernández-Alamos MM Vallejo S Primo-Yúfera E Vargas-Arispuro I 《Pest management science》2003,59(11):1245-1249
Four polymethoxylated flavones (3,5,6,7,3',4'-hexamethoxyflavone, 3,5,6,7,8,3',4'-heptamethoxyflavone, 5,6,7,8,4'-pentamethoxyflavone and 5,6,7,8,3',4'-hexamethoxyflavone) were isolated and characterized from cold-pressed orange oil. Their antifungal activities were evaluated against Colletotrichum gloeosporioides (Penz) Penz & Sacc, a major plant pathogen of fruits that causes significant damage to crops in tropical, sub-tropical and temperate regions. Methoxylated flavones were effective in inhibiting mycelial growth of the fungus. As flavone concentration increased, mycelial growth decreased. 5,6,7,8,3',4'-Hexamethoxyflavone completely inhibited the growth of Cgloeosporioides at a concentration of 100 microg ml(-1). 相似文献
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Victor SR Crisóstomo FR Bueno FC Pagnocca FC Fernandes JB Correa AG Bueno OC Hebling MJ Bacci Júnior M Vieira PC da Silva MF 《Pest management science》2001,57(7):603-608
The development of Leucoagaricus gongylophorus, the fungus cultured by the leaf-cutting ant Atta sexdens was inhibited in vitro by synthetic compounds containing the piperonyl group. In addition, worker ants that were fed daily on an artificial diet to which these compounds were added had a higher mortality rate than the controls. The inhibition of the fungal growth increased with the size of the carbon side chain ranging from C1 through C8 and decreasing thereafter. 1-(3,4-Methylenedioxybenzyloxy)octane (compound 5) was the most active compound and inhibited the fungal development by 80% at a concentration of 15 micrograms ml-1. With worker ants the toxic effects started with compound 5 and increased with the number of carbons in the side chain. Thus, for the same concentration (100 micrograms ml-1) the mortality rates observed after 8 days of diet ingestion were 82%, 66% and 42%, for 1-(3,4-methylenedioxybenzyloxy)decane, 1-(3,4-methylenedioxybenzyloxy)dodecane and compound 5, respectively, whereas with commercial piperonyl butoxide the mortality was 68%. The latter compound, which is known as a synergist insecticide, was as inhibitory to the symbiotic fungus as the synthetic compound 5. The possibility of controlling these insects in the future using compounds that can target simultaneously both organisms is discussed. 相似文献