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Natural Compound to Biocontrol Agrarian Pests

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (31 July 2019) | Viewed by 35484

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Prof. Dr. Antonio Evidente

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1. Department of Chemical Sciences, University of Naples “Federico II”, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli, Italy
2. Institute of Sciences of Food Production, National Research Council, Via Amendola 122/O, 70125 Bari, Italy
Interests: Fungi; Bacterial; plant; metabolites; chemistry; spectroscopy; stereochemistry; biological activity; structure-activity relationships
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Dear Colleagues,

Pests, including weedy and parasitic plants, microbial pathogens, insect, etc., are one of the most serious problems for agriculture, affecting the production of healthy harvest in sufficient amounts, as they also infests economically important crops causing marked losses in agrarian yield. Pests also generate significant ecological problems, in particular to forests, ornamental heritages, archaeological areas, and green-house pasture industries. Agrarian pests include pathogenic fungi and bacteria that infect the host plants frequently causing their death, weed and parasitic plants, such as Striga, Orobanche, Phelipanche, and Cuscuta, which are root parasitic plants that acquire nutrients and water from their host causing significant harm, and insects that seriously damage or completely eat their hosts. Several management strategies have been applied to control the agrarian production, including mechanical, cultural, chemical, and biological strategies, but they have not provided a satisfactory solution to plant pest diffusion. The massive use of chemicals, including fungicides, bacteriocides, herbicides, and insecticides, differing widely with respect to their spectrum of action, unit activity, crop safety, toxicology, and environmental effects, has increased pest resistance; in addition, environmental and toxicological concerns raise questions over their large-scale use. These problems urge to focus on developing alternative strategies based on the use of natural products, in particular, bacterial, fungal, and plant metabolites, alone as natural pesticides, or in combination with producers or allelopathic plants extracts or root exudates, for a more efficient, integrated management. The development of new, efficient, and safe formulations of natural pesticides is one of the most important objectives to be reached. The complexation of natural products with available or new biopolymers could also be a means to enhance the bioavailability of poorly soluble metabolites by increasing their solubility in water.

Prof. Dr. Antonio Evidente
Guest Editor

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Keywords

safe pesticides (bacteriocides, fungicides, herbicides, insecticides)
source and chemical characterization
natural products
biological activities
chemical modification
formulation in biopolymers
integrated management

Published Papers (10 papers)

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Research

11 pages, 1905 KiB

Open AccessFeature PaperArticle

Inuloxin E, a New Seco-Eudesmanolide Isolated from Dittrichia viscosa, Stimulating Orobanche cumana Seed Germination

by Marco Masi, Mónica Fernández-Aparicio, Roukia Zatout, Angela Boari, Alessio Cimmino and Antonio Evidente

Molecules 2019, 24(19), 3479; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24193479 - 25 Sep 2019

Cited by 8 | Viewed by 2439

Abstract

A new sesquiterpenoid belonging to the subgroup seco-eudesmanolides and named inuloxin E was isolated from Dittrichia viscosa, together with the already known sesquiterpenoids inuloxins A–D and α-costic acid. Inuloxin E was characterized by spectroscopic data (essentially NMR and ESI MS) as 3-methylene-6-(1-methyl-4-oxo-pentyl)-3a,4,7,7a-tetrahydro-3H-benzofuran-2-one. Its relative configuration was determined by comparison with the closely related inuloxin D and chemical conversion of inuloxin E into inuloxin D and by the observed significant correlation in the NOESY spectrum. Both inuloxins D and E induced germination of the parasitic weed Orobanche cumana, but were inactive on the seeds of Orobanche minor and Phelipanche ramosa. The germination activity of some hemisynthetic esters of inuloxin D was also investigated. Full article

(This article belongs to the Special Issue Natural Compound to Biocontrol Agrarian Pests)

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10 pages, 1430 KiB

Open AccessFeature PaperArticle

Synthesis and Herbicidal Activity Against Buffelgrass (Cenchrus ciliaris) of (±)-3-deoxyradicinin

by Giulia Marsico, Maria Sabrina Ciccone, Marco Masi, Fabrizio Freda, Massimo Cristofaro, Antonio Evidente, Stefano Superchi and Patrizia Scafato

Molecules 2019, 24(17), 3193; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24173193 - 03 Sep 2019

Cited by 12 | Viewed by 3415

Abstract

A novel synthetic strategy for obtainment of (±)-3-deoxyradicinin (2) is reported. This synthetic methodology is more efficient than those previously reported in the literature and also shows higher versatility towards the introduction of different side-chains at both C-7 and C-2. The obtained compound (±)-2 shows phytotoxicity against the grass-weed buffelgrass comparable to that of the natural phytotoxin radicinin (1). Therefore, (±)-2 can constitute a more practical synthetic alternative to 1 as bioherbicide for buffelgrass control. Full article

(This article belongs to the Special Issue Natural Compound to Biocontrol Agrarian Pests)

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11 pages, 2146 KiB

Open AccessFeature PaperArticle

Assignment Through Chiroptical Methods of The Absolute Configuration of Fungal Dihydropyranpyran-4-5-Diones Phytotoxins, Potential Herbicides for Buffelgrass (Cenchrus ciliaris) Biocontrol

by Ernesto Santoro, Giuseppe Mazzeo, Giulia Marsico, Marco Masi, Giovanna Longhi, Stefano Superchi, Antonio Evidente and Sergio Abbate

Molecules 2019, 24(17), 3022; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24173022 - 21 Aug 2019

Cited by 13 | Viewed by 2659

Abstract

Radicinin and cochliotoxin (1 and 2) two phytotoxic pyranpyran-4,5-diones were isolated together with their close metabolites 3-epi-radicinin, radicinol, and its 3-epimer (3–5), from the culture filtrates of Cochliobolus australiensis, a fungus proposed as mycoherbcide for biocontrol of buffelgrass, a very noxious and dangerous weed. The absolute configuration of cochliotoxin was determined by chiroptical Optical Rotatory Dispersion (ORD), Electronic Circular Dichroism (ECD), and Vibrational Circular Dichroism (VCD)) and computational methods. The same methods were used to confirm that of radicinin, radicinol and their 3-epimers, previously determined with chemical, spectroscopic and ECD methods. Full article

(This article belongs to the Special Issue Natural Compound to Biocontrol Agrarian Pests)

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10 pages, 2889 KiB

Open AccessArticle

Dirhamnolipid Produced by the Pathogenic Fungus Colletotrichum gloeosporioides BWH-1 and Its Herbicidal Activity

by Zhaolin Xu, Mengying Shi, Yongqing Tian, Pengfei Zhao, Yifang Niu and Meide Liao

Molecules 2019, 24(16), 2969; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24162969 - 16 Aug 2019

Cited by 11 | Viewed by 3034

Abstract

Fungal phytotoxins used as ecofriendly bioherbicides are becoming efficient alternatives to chemical herbicides for sustainable weed management. Previous study found that cultures of the pathogenic fungus Colletotrichum gloeosporioides BWH-1 showed phytotoxic activity. This study further isolated the major phytotoxin from cultures of the strain BWH-1 using bioactivity-guided isolation, by puncturing its host plant for an activity test and analyzing on the HPLC-DAD-3D mode for a purity check. Then, the active and pure phytotoxin was characterized as a dirhamnolipid (Rha-Rha-C10-C10) using the NMR, ESIMS, IR and UV methods. The herbicidal activity of dirhamnolipid was evaluated by the inhibition rate on the primary root length and the fresh plant weight of nine test plants, and the synergistic effect when combining with commercial herbicides. Dirhamnolipid exhibited broad herbicidal activity against eight weed species with IC₅₀ values ranging from 28.91 to 217.71 mg L⁻¹ and no toxicity on Oryza sativa, and the herbicidal activity could be synergistically improved combining dirhamnolipid with commercial herbicides. Thus, dirhamnolipid that originated from C. gloeosporioides BWH-1 displayed the potential to be used as a bioherbicide alone, or as an adjuvant added into commercial herbicides, leading to a decrease in herbicides concentration and increased control efficiency. Full article

(This article belongs to the Special Issue Natural Compound to Biocontrol Agrarian Pests)

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13 pages, 677 KiB

Open AccessFeature PaperArticle

Laboratory Evaluation of Natural and Synthetic Aromatic Compounds as Potential Attractants for Male Mediterranean fruit Fly, Ceratitis capitata

by Nurhayat Tabanca, Marco Masi, Nancy D. Epsky, Paola Nocera, Alessio Cimmino, Paul E. Kendra, Jerome Niogret and Antonio Evidente

Molecules 2019, 24(13), 2409; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24132409 - 29 Jun 2019

Cited by 8 | Viewed by 3326

Abstract

Ceratitis capitata, the Mediterranean fruit fly, is one of the most serious agricultural pests worldwide responsible for significant reduction in fruit and vegetable yields. Eradication is expensive and often not feasible. Current control methods include the application of conventional insecticides, leading to pesticide resistance and unwanted environmental effects. The aim of this study was to identify potential new attractants for incorporation into more environmentally sound management programs for C. capitata. In initial binary choice bioassays against control, a series of naturally occurring plant and fungal aromatic compounds and their related analogs were screened, identifying phenyllactic acid (7), estragole (24), o-eugenol (21), and 2-allylphenol (23) as promising attractants for male C. capitata. Subsequent binary choice tests evaluated five semisynthetic derivatives prepared from 2-allylphenol, but none of these were as attractive as 2-allylphenol. In binary choice bioassays with the four most attractive compounds, males were more attracted to o-eugenol (21) than to estragole (24), 2-allylphenol (23), or phenyllactic acid (7). In addition, electroantennography (EAG) was used to quantify antennal olfactory responses to the individual compounds (1–29), and the strongest EAG responses were elicited by 1-allyl-4-(trifluoromethyl)benzene (11), estragole (24), 4-allyltoluene (14), trans-anethole (9), o-eugenol (21), and 2-allylphenol (23). The compounds evaluated in the current investigation provide insight into chemical structure–function relationships and help direct future efforts in the development of improved attractants for the detection and control of invasive C. capitata. Full article

(This article belongs to the Special Issue Natural Compound to Biocontrol Agrarian Pests)

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8 pages, 370 KiB

Open AccessCommunication

Potential of a Small Molecule Carvacrol in Management of Vegetable Diseases

by Qingchun Liu, Kang Qiao and Shouan Zhang

Molecules 2019, 24(10), 1932; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24101932 - 20 May 2019

Cited by 19 | Viewed by 3408

Abstract

Carvacrol, a plant-derived volatile small molecule, is effective against various agents that can cause damage to humans, the food processing industry, and plants, and is considered a safe substance for human consumption. In this short communication, previous studies on the effectiveness of carvacrol against various agents, particularly plant pathogens and their associated mechanisms are described. In our study, carvacrol was found to be effective on media against several soilborne pathogens and in planta against three foliar pathogens (Xanthomonas perforans, Alternaria tomatophila, and Podosphaeraxanthii) of important vegetable crops in south Florida of the United States. Current research findings indicated that the effectiveness of carvacrol against various plant pathogens tested was associated with its direct bactericidal/fungicidal effect, which was affected greatly by its volatility. Development of new formulations to overcome the volatility and to prolong the effectiveness of carvacrol was also presented. Our studies on carvacrol suggested that, with advanced development of new formulations, carvacrol could be used as a promising tool in the integrated pest management for bacterial, fungal, and viral pathogens of important vegetable crops in Florida, the USA, and the world. Full article

(This article belongs to the Special Issue Natural Compound to Biocontrol Agrarian Pests)

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14 pages, 3819 KiB

Open AccessArticle

Antifungal Activity of Eugenol Derivatives against Botrytis Cinerea

by Andrés F. Olea, Angelica Bravo, Rolando Martínez, Mario Thomas, Claudia Sedan, Luis Espinoza, Elisabeth Zambrano, Denisse Carvajal, Evelyn Silva-Moreno and Héctor Carrasco

Molecules 2019, 24(7), 1239; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24071239 - 29 Mar 2019

Cited by 62 | Viewed by 5773

Abstract

Botrytis cinerea is a worldwide spread fungus that causes the grey mold disease, which is considered the most important factor in postharvest losses in fresh fruit crops. Consequently, the control of gray mold is a matter of current and relevant interest for agricultural industries. In this work, a series of phenylpropanoids derived from eugenol were synthesized and characterized. Their effects on the mycelial growth of a virulent and multi-resistant isolate of B. cinerea (PN2) have been evaluated and IC₅₀ values for the most active compounds range between 31–95 ppm. The antifungal activity exhibited by these compounds is strongly related to their chemical structure, i.e., increasing activity has been obtained by isomerization of the double bond or introduction of a nitro group on the aromatic ring. Based on the relationship between the fungicide activities and chemical structure, a mechanism of action is proposed. Finally, the activity of these compounds is higher than that reported for the commercial fungicide BC-1000 that is currently employed to combat this disease. Thus, our results suggest that these compounds are potential candidates to be used in the design of new and effective control with inspired natural compounds of this pathogen. Full article

(This article belongs to the Special Issue Natural Compound to Biocontrol Agrarian Pests)

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11 pages, 1847 KiB

Open AccessArticle

Radicinin, a Fungal Phytotoxin as a Target-Specific Bioherbicide for Invasive Buffelgrass (Cenchrus ciliaris) Control

by Marco Masi, Fabrizio Freda, Felicia Sangermano, Viola Calabrò, Alessio Cimmino, Massimo Cristofaro, Susan Meyer and Antonio Evidente

Molecules 2019, 24(6), 1086; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24061086 - 19 Mar 2019

Cited by 25 | Viewed by 3504

Abstract

The fungal pathogens Cochliobolus australiensis and Pyricularia grisea have recently been isolated from diseased leaves of buffelgrass (Cenchrus ciliaris) in its North American range, and their ability to produce phytotoxic metabolites that could potentially be used as natural herbicides against this invasive weed was investigated. Fourteen secondary metabolites obtained from in vitro cultures of these two pathogens were tested by leaf puncture assay on the host plant at different concentrations. Radicinin and (10S, 11S)-epi-pyriculol proved to be the most promising compounds. Thus, their phytotoxic activity was also evaluated on non-host indigenous plants. Radicinin demonstrated high target-specific toxicity on buffelgrass, low toxicity to native plants, and no teratogenic, sub-lethal, or lethal effects on zebrafish (Brachydanio rerio) embryos. It is now under consideration for the development of a target-specific bioherbicide to be used against buffelgrass in natural systems where synthetic herbicides cause excessive damage to native plants. Full article

(This article belongs to the Special Issue Natural Compound to Biocontrol Agrarian Pests)

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15 pages, 1806 KiB

Open AccessArticle

Insecticidal Activities of Chloramphenicol Derivatives Isolated from a Marine Alga-Derived Endophytic Fungus, Acremonium vitellinum, against the Cotton Bollworm, Helicoverpa armigera (Hübner) (Lepidoptera: Noctuidae)

by Dan Chen, Peng Zhang, Tong Liu, Xiu-Fang Wang, Zhao-Xia Li, Wei Li and Feng-Long Wang

Molecules 2018, 23(11), 2995; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules23112995 - 16 Nov 2018

Cited by 17 | Viewed by 3795

Abstract

A great deal of attention has been focused on the secondary metabolites produced by marine endophytic fungi, which can be better alternatives to chemicals, such as biopesticides, for control of polyphagous pests. On the basis of its novel biocontrol attributes, chemical investigation of a marine alga-derived endophytic fungus, Acremonium vitellinum, resulted in the isolation of three chloramphenicol derivatives (compounds 1–3). Their chemical structures were elucidated by detailed analysis of their nuclear magnetic resonance spectra, high-resolution electrospray ionization mass spectrometry, and by comparison with the data available in the literature. In this paper, compound 2 was firstly reported as the natural origin of these fungal secondary metabolites. The insecticidal activities of compounds 1–3 against the cotton bollworm, Helicoverpa armigera, were evaluated. The natural compound 2 presented considerable activity against H. armigera, with an LC₅₀ value of 0.56 ± 0.03 mg/mL (compared to matrine with an LC₅₀ value of 0.24 ± 0.01 mg/mL). Transcriptome sequencing was used to evaluate the molecular mechanism of the insecticidal activities. The results presented in this study should be useful for developing compound 2 as a novel, ecofriendly and safe biopesticide. Full article

(This article belongs to the Special Issue Natural Compound to Biocontrol Agrarian Pests)

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15 pages, 2524 KiB

Open AccessFeature PaperArticle

Curvulin and Phaeosphaeride A from Paraphoma sp. VIZR 1.46 Isolated from Cirsium arvense as Potential Herbicides

by Ekaterina Poluektova, Yuriy Tokarev, Sofia Sokornova, Leonid Chisty, Antonio Evidente and Alexander Berestetskiy

Molecules 2018, 23(11), 2795; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules23112795 - 28 Oct 2018

Cited by 16 | Viewed by 3395

Abstract

Phoma-like fungi are known as producers of diverse spectrum of secondary metabolites, including phytotoxins. Our bioassays had shown that extracts of Paraphoma sp. VIZR 1.46, a pathogen of Cirsium arvense, are phytotoxic. In this study, two phytotoxically active metabolites were isolated from Paraphoma sp. VIZR 1.46 liquid and solid cultures and identified as curvulin and phaeosphaeride A, respectively. The latter is reported also for the first time as a fungal phytotoxic product with potential herbicidal activity. Both metabolites were assayed for phytotoxic, antimicrobial and zootoxic activities. Curvulin and phaeosphaeride A were tested on weedy and agrarian plants, fungi, Gram-positive and Gram-negative bacteria, and on paramecia. Curvulin was shown to be weakly phytotoxic, while phaeosphaeride A caused severe necrotic lesions on all the tested plants. To evaluate phaeosphaeride A’s herbicidal efficacy, the phytotoxic activity of this compound in combination with five different adjuvants was studied. Hasten at 0.1% (v/v) was found to be the most potent and compatible adjuvant, and its combination with 0.5% (v/v) semi-purified extract of Paraphoma sp. VIZR 1.46 solid culture exhibited maximum damage to C. arvense plants. These findings may offer significant importance for further investigation of herbicidal potential of phaeosphaeride A and possibly in devising new herbicide of natural origin. Full article

(This article belongs to the Special Issue Natural Compound to Biocontrol Agrarian Pests)

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