1,721,210 research outputs found
Fungal phytotoxins for control of Cirsium arvense and Sonchus arvensis
No full textPerennial weeds, including Cirsium arvense and Sonchus arvensis, are a common problem in crop fields, especially in agricultural systems with reduced herbicide usage. Herbicides recommended for control of these perennials generally are restricted to only a few active ingredients that tend to have low selectivity, especially on dicot crops. Microbial phytotoxins or their synthetic analogues may be candidates for new weed-control options. Many plant pathogens, especially necrotrophic or hemibiotrophic fungi, produce a range of phytotoxins responsible for disease damage and may be a source of such useful metabolites. Several pathogens, including Stagonospora cirsii and Ascochyta sonchi, were found commonly on C. arvense and S. arvensis, and these fungi also produce phytotoxic metabolites. Phyllosticta cirsii and Phomopsis cirsii, belonging to two well-known toxin-producing genera, have also been proposed for biocontrol of C. arvense. Phytotoxins isolated from these fungal pathogens are metabolites belonging to several classes of natural compounds including enol pyruvic acid derivatives, cytochalasins, nonenolides, oxazatricycloalkenones, pentasubstituted bicyclooctatrienyl ester of acetic acid, pentasubstituted hexahydrobenzodioxine carboxylic acid methyl ester, and β-nitropropionic acid. Some of these metabolites may be used as biomarkers, for studies on mode of action and development of structure-activity relationships
Phytotoxic Terpenes Produced by Phytopathogenic Fungi and Allelopathic Plants
No full textThis review is about the isolation as well as chemical and biological characterization of simple and complex mono-, sesqui-, di-, sester- and tri-terpenes produced by fungal pathogens of agrarian and forest plants and by some allelopathic plants. In several cases, the structure activity relationships are also discussed, as well as their potential application in agriculture as natural safe herbicides, fungicides and bactericides. Furthermore, the potential application of some fungal terpenes as anticancer compounds with a new mode of action is also discussed
The effect of stereochemistry on the biological activity of natural phytotoxins, fungicides, insecticides and herbicides
No full textPhytotoxins are secondary microbial metabolites that play an essential role in the development of disease symptoms induced by fungi on host plants. Although phytotoxins can cause extensive—and in some cases devastating—damage to agricultural crops, they can also represent an important tool to develop natural herbicides when produced by fungi and plants to inhibit the growth and spread of weeds. An alternative strategy to biologically control
parasitic plants is based on the use of plant and fungal metabolites, which stimulate seed germination in the absence of the host plant. Nontoxigenic fungi also produce bioactive metabolites with potential fungicide and insecticide activity, and could be applied for crop protection. All these metabolites represent important tools to develop eco-friendly pesticides. This review deals with the relationships between the biological activity of some phytotoxins, seed germination stimulants, fungicides and insecticides, and their stereochemistr
Phytotoxic nonenolides produced by fungi pathogenic for crops and weeds
No full textPinolidoxin, 2-hexadionoyloxy-7-hydroxy-9-propyl-5-nonen-9-olide, is the first phytotoxic nonenolide, isolated from some of us on 1993, together three minor ones as the main toxin produced by Ascochyta pinodes.1 This is the fungal causal agent of pea anthracnose.
Successively, phytotoxic nonenolide as putaminoxin, the main one, the close related putaminoxins B-D were also isolated from Phoma putaminum, the fungus proposed as mycoherbicide to biological control Erigeron annuus, a widespread weed in the pasture of northern emisphere.2 Later, stagonolide, a new nonenolide, was also isolated as the main toxin from liquid culture of Stagonospora cirsii proposed for the biological control of Cirsium arvense and Sonchus arvensis, two very noxious perennial weeds of several agrarian crops, essentially cereals. Successively nine related new nonenolides were isolated together to the well known modiolide A, from solid cultures of the same fungus.3 So that some studies were carried out using the toxins some their natural analogues and hemisynthetic derivatives to carry out studies on the structure-activity relationships and on their mode of action.4
Recently, from a strain of Ascochyta pinodes isolated in Spain from infected pea and grown in liquid culture were isolated herbarumin II, and 2-epi-herbarumin II together with a new nonenolide, named pinolide. In this communication an overview on the phytotoxic fungal nonenolides will be illustrated as well as the chemical and biological characterization of pinolide and the potential practical application of some of them as natural eco-friendly herbicides
Stagonolides G-I and modiolide A, nonenolides produced by Stagonospora cirsii, a potential mycoherbicide for Cirsium arvense
No full textFungal phytotoxins with potential herbicidal activity: chemical and biological characterization
No full textFungal phytotoxins are secondary metabolites playing an important role in the induction of disease symptoms interfering with host plant physiological processes. Although fungal pathogens represent a heavy constraint for agrarian production and for forest and environmental heritage, they can also represent an ecofriendly alternative to manage weeds. Indeed, the phytotoxins produced by weed pathogenic fungi are an efficient tool to design natural, safe bioherbicides. Their use could avoid that of synthetic pesticides causing resistance in the host plants and the long term impact of residues in agricultural products with a risk to human and animal health. The isolation and structural and biological characterization of phytotoxins produced by pathogenic fungi for weeds, including parasitic plants, are described. Structure activity relationships and mode of action studies for some phytotoxins are also reported to elucidate the herbicide potential of these promising fungal metabolites
Production of phytotoxins by Phoma exigua var. exigua, a potential mycoherbicide against perennial thistles
No full textThe potential of the different Phoma exigua var. exigua strains for the biocontrol of the perennial weeds Sonchus arvensis and Cirsium arvense, occurring throughout temperate regions of the world, has been evaluated in previous studies. The majority of the above strains produced ascosonchine, a newly discovered enol tautomer of 4- pyridylpyruvic acid, whereas strains C-177 and S-9, though virulent to weeds, did not produce the above metabolite. In this study, it was demonstrated that the above two strains, grown in liquid and solid cultures, produced p-hydroxybenzaldehyde, cytochalasins B, F, Z2 and Z3, and deoxaphomin. When assayed on the leaves of both C. arvense and S. arvensis, p-hydroxybenzaldehyde was inactive, whereas deoxaphomin demonstrated the highest level of toxicity on leaves of S. arvensis. Cytochalasin Z2 appeared to be the less toxic cytochalasan on both plants according to the lack of the secondary hydroxyl group on C-7. Production of cytochalasins by P. exigua var. exigua strains isolated from C. arvense and S. arvensis is discussed in relation to chemotaxonomy and the biocontrol potential of the fungus
Polyphenols as fungal phytotoxins, seed germination stimulants and phytoalexins
No full textThis review deals with the sources and chemical and biological characterization of phytotoxic polyphenols produced essentially by pathogenic fungi of forest and crop plants and of weeds. Their potential use as natural herbicides and fungicides is discussed. The use of some polyphenols which could be applied as an alternative method to control parasitic weeds, the so called “suicidal germination”, will be covered. The sources and the isolation and identification of polyphenols produced by some crop plants in consequence of the attack of pathogenic fungi as plant defence compounds (phytoalexins), are also described
Pyrenophoric Acid, a Phytotoxic Sesquiterpenoid Penta-2,4-dienoic Acid Produced by a Potential Mycoherbicide,Pyrenophora semeniperda
No full textA new phytotoxic sesquiterpenoid penta-2,4-dienoic acid, named pyrenophoric acid, was isolated from solid wheat seed culture of Pyrenophora semeniperda, a fungal pathogen proposed as a mycoherbicide for biocontrol of cheatgrass (Bromus tectorum) and other annual bromes. These bromes are serious weeds in winter cereals and also on temperate semiarid rangelands. Pyrenophoric acid was characterized as (2Z,4E)-5-[(7S,9S,10R,12R)-3,4-dihydroxy-2,2,6-trimethylcyclohexyl)]-3-methylpenta-2,4-dienoic acid by spectroscopic and chemical methods. The relative stereochemistry of pyrenophoric acid was assigned using 1H,1H couplings and NOESY experiments, while its absolute configuration
was determined by applying the advanced Mosher’s method. Pyrenophoric acid is structurally quite closely related to the plant growth regulator abscisic acid. When bioassayed in a cheatgrass coleoptile elongation test at 10−3 M, pyrenophoric acid showed strong phytotoxicity, reducing coleoptile elongation by 51% relative to the control. In a mixture at 10−4 M, its negative effect on coleoptile elongation was additive with that of cytochalasin B, another phytotoxic compound found in the wheat seed culture extract of this fungus, demonstrating that the extract toxicity observed in earlier studies was due to the combined action of multiple phytotoxic compounds
Bacterial Lipodepsipeptides and Some of Their Derivatives and Cyclic Dipeptides as Potential Agents for Biocontrol of Pathogenic Bacteria and Fungi of Agrarian Plants
No full textBiotic stresses (fungi, bacteria, insects, weeds, etc.) are some of the most important causes of the decrease in the quality and quantity of crops that could become an emergency due to a noteworthy increase in the world population. Thus, to overcome these problems, massive use of chemical pesticides has been carried out with heavy consequences for environmental pollution and food safety. An eco-friendly alternative can be using natural compound-based biopesticides with high efficacy and selectivity. Some bacterial lipodepsipeptides (tolaasins I, II, A, D, and E and WLIP together with hexacetyl- and tetrahydro-tolaasin I and WLIP methyl ester) and cyclic dipeptides (cyclo(l-Pro-l-Tyr), cyclo(d-Pro-l-Tyr), cyclo(l-Pro-l-Val), and cyclo(l-Pro-l-Leu)) were assayed against several pathogenic bacteria and fungi of important agrarian plants. Lipodepsipeptides showed strong growth inhibition of all microorganisms tested in the range of 0.1-0.8 μg/mL, while cyclodipeptides, despite preserving this ability, showed a noteworthily reduced antimicrobial activity being active only in the range of 15-900 μg/mL. Among the lipodepsipeptides and cyclic dipeptides assayed, tolaasin d and cyclo(l-Pro-l-Tyr) (also named maculosin-1) appeared to be the most toxic compounds. Some structure-activity relationships of lipodepsipeptides were also discussed along with their practical application as biopesticides in agriculture
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