Your browser doesn't support javascript.
loading
Show: 20 | 50 | 100
Results 1 - 20 de 337
Filter
1.
J Agric Food Chem ; 72(28): 15512-15522, 2024 Jul 17.
Article in English | MEDLINE | ID: mdl-38959331

ABSTRACT

Root-knot nematodes pose a serious threat to crops by affecting production and quality. Over a period of time, substantial work has been done toward the development of effective and environmentally benign nematicidal compounds. However, due to the inefficiencies of previously reported synthetics in achieving the target of safe, selective, and effective treatment, it is necessary to develop new efficacious and safer nematicidal agents considering human health and environment on top priority. This work aims to highlight the efficient and convenient l-proline catalyzed synthesis of pyrano[3,2-c]pyridone and their use as potential nematicidal agents. In vitro results of larval mortality and egg hatching inhibition revealed maximum nematicidal activity against Meloidogyne incognita from compounds 15b, 15m, and 15w with LC50 values of 28.8, 46.8, and 49.18 µg/mL at 48 h, respectively. Under similar conditions, pyrano[3,2-c]pyridones derivatives 15b (LC50 = 28.8 µg/mL) was found at par with LC50 (26.92 µg/mL) of commercial nematicide carbofuran. The in vitro results were further validated with in silico studies with the most active compound 15b nematicidal within the binding to the pocket of acetylcholine esterase (AChE). In docking, binding free energy values for compound 15b were found to be -6.90 kcal/mol. Results indicated that pyrano[3,2-c]pyridone derivatives have the potential to control M. incognita.


Subject(s)
Antinematodal Agents , Drug Design , Molecular Docking Simulation , Pyridones , Tylenchoidea , Tylenchoidea/drug effects , Animals , Antinematodal Agents/pharmacology , Antinematodal Agents/chemistry , Antinematodal Agents/chemical synthesis , Pyridones/chemistry , Pyridones/pharmacology , Pyridones/chemical synthesis , Structure-Activity Relationship , Larva/drug effects , Larva/growth & development , Plant Diseases/parasitology , Molecular Structure
2.
Sci Rep ; 14(1): 13500, 2024 06 12.
Article in English | MEDLINE | ID: mdl-38867066

ABSTRACT

The continuous search for natural product-based biopesticides from fungi isolated from untapped sources is an effective tool. In this study, we studied a pre-selected fungal endophyte, isolate Aa22, from the medicinal plant Artemisia absinthium, along with the antifungal, insect antifeedant and nematicidal compounds present in the extract. The endophyte Aa22 was identified as Stemphylium solani by molecular analysis. The antifungal activity was tested by broth microdilution against Fusarium solani, F. oxysporum, F. moniliforme and Botrytis cinerea, the insect antifeedant by choice bioassays against Spodoptera littoralis, Myzus persicae and Rhopalosiphum padi and the in vitro mortality against the root-knot nematode Meloiydogyne javanica. The structures of bioactive compounds were determined on the basis of 1D and 2D NMR spectroscopy and mass spectrometry. The ethyl acetate extract obtained from the solid rice fermentation showed mycelial growth inhibition of fungal pathogens (EC50 0.08-0.31 mg/mL), was antifeedant to M. persicae (99%) and nematicidal (68% mortality). A bioguided fractionation led to the isolation of the new compound stempholone A (1), and the known stempholone B (2) and stemphol (3). These compounds exhibited antifeedant (EC50 0.50 mg/mL), antifungal (EC50 0.02-0.43 mg/L) and nematicidal (MLD 0.5 mg/mL) activities. The extract activities can be explained by 3 (antifungal), 1-3 (antifeedant) and 1 (nematicidal). Phytotoxicity tests on Lolium perenne and Lactuca sativa showed that the extract and 1 increased L. sativa root growth (121-130%) and 1 reduced L. perenne growth (48-49%). These results highlight the potential of the endophytic fungi Aa22 as biotechnological source of natural product-based biopesticides.


Subject(s)
Antifungal Agents , Antinematodal Agents , Endophytes , Animals , Endophytes/chemistry , Antifungal Agents/pharmacology , Antifungal Agents/chemistry , Antifungal Agents/isolation & purification , Antinematodal Agents/pharmacology , Antinematodal Agents/isolation & purification , Antinematodal Agents/chemistry , Fusarium/drug effects , Spodoptera/drug effects , Spodoptera/growth & development , Ascomycota/drug effects , Botrytis/drug effects , Botrytis/growth & development , Microbial Sensitivity Tests , Tylenchoidea/drug effects
3.
J Nat Prod ; 87(6): 1532-1539, 2024 Jun 28.
Article in English | MEDLINE | ID: mdl-38853528

ABSTRACT

Nematode infections affect a fifth of the human population, livestock, and crops worldwide, imposing a burden to global public health and economies, particularly in developing nations. Resistance to commercial anthelmintics has increased over the years in livestock infections and driven the pursuit for new drugs. We herein present a rapid, cost-effective, and automated assay for nematicide discovery using the free-living nematode Caenorhabditis elegans to screen a highly diverse natural product library enriched in bioactive molecules. Screening of 10,240 fractions obtained from extracts of various biological sources allowed the identification of 7 promising hit fractions, all from marine sponges. These fractions were further assayed for nematicidal activity against the sheep nematode parasite Haemonchus contortus and for innocuity in zebrafish. The most active extracts against parasites and innocuous toward vertebrates belong to two chemotypes. High-performance liquid chromatography (HPLC) coupled with nuclear magnetic resonance (NMR) revealed that the most abundant compound in one chemotype is halaminol A, an aminoalcohol previously identified in a small screen against H. contortus. Terpene-nucleotide hybrids known as agelasines predominate in the other chemotype. This study reinforces the power of C. elegans for nematicide discovery from large collections and the potential of the chemical diversity derived from marine invertebrate biota.


Subject(s)
Antinematodal Agents , Caenorhabditis elegans , Porifera , Animals , Porifera/chemistry , Antinematodal Agents/pharmacology , Antinematodal Agents/chemistry , Caenorhabditis elegans/drug effects , Molecular Structure , Zebrafish , Haemonchus/drug effects , Chromatography, High Pressure Liquid/methods
4.
Int J Biol Macromol ; 269(Pt 2): 132131, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38719017

ABSTRACT

Chitosan oligosaccharide (COS) modification is a feasible way to develop novel green nematicides. This study involved the synthesis of various COS sulfonamide derivatives via hydroxylated protection and deprotection, which were then characterized using NMR, FTIR, MS, elemental analysis, XRD, and TG/DTG. In vitro experiments found that COS-alkyl sulfonamide derivatives (S6 and S11-S13) exhibited high mortality (>98 % at 1 mg/mL) against Meloidogyne incognita second-instar larvaes (J2s) among the derivatives. S6 can cause vacuole-like structures in the middle and tail regions of the nematode body and effectively inhibit egg hatching. In vivo tests have found that S6 has well control effects and low plant toxicity. Additionally, the structure-activity studies revealed that S6 with a high degree of substitution, a low molecular weight, and a sulfonyl bond on the amino group of the COS backbone exhibited increased nematicidal activity. The sulfonamide group is a potential active group for developing COS-based nematicides.


Subject(s)
Antinematodal Agents , Chitosan , Oligosaccharides , Sulfonamides , Tylenchoidea , Chitosan/chemistry , Chitosan/pharmacology , Animals , Tylenchoidea/drug effects , Antinematodal Agents/pharmacology , Antinematodal Agents/chemistry , Oligosaccharides/chemistry , Oligosaccharides/pharmacology , Sulfonamides/chemistry , Sulfonamides/pharmacology , Structure-Activity Relationship , Larva/drug effects
5.
Acta Trop ; 256: 107274, 2024 Aug.
Article in English | MEDLINE | ID: mdl-38810900

ABSTRACT

The aim of this study was to evaluate the circadian and seasonal variation of Ageratum conyzoides essential oil (EO) and its nematicidal effect on the free-living nematode Caenorhabditis elegans as a model for parasitic helminths. For the seasonal study, the plants were collected from January to December 2022, at 6 a.m., and to assess the circadian rhythm, the plants were collected in April (rainy season) and October (dry season), at 6, 9, 12 a.m. and 3 and 6 p.m. The fresh plants were then subjected to hydrodistillation, and their chemical composition was analyzed using gas chromatography coupled with mass spectrometry (GC-MS). The motility test with C. elegans was carried out. The primary constituent of the oils was precocene I (65.97 to 78.42 %, respectively), followed by E-caryophyllene (6.04 to 12.16 %), comprising an average of 79.87 % of the composition throughout the year. The average yields of EOs were slightly higher in the rainy season, at 0.68 %, compared to the dry season, at 0.62 %. High light hours in the rainy season (12 a.m., 0.96 %) and in the dry season (9 a.m., 0.88 %) seem to contribute to higher daily oil yields. It was observed that the variation between the main constituents of A. conyzoides occurs in inverse proportion when analyzing the main classes of compounds present in the oils: chromenes (CH) and sesquiterpene hydrocarbons (SH). And that the month of March had the highest content of E-caryophyllene (12.16 %) when compared to the other months of the year. On the other hand, January and December had the lowest levels of precocene I (65.97 and 66.85 %). The IC50 of the EO of A. conyzoides varied according to the month and time of collection. The EO obtained in January was the most effective against C. elegans, with an IC50 of 0.01 mg/mL. Thus, A. conyzoides EO could be an alternative for nematode control, exhibiting greater efficacy if extracted during specific seasonal periods.


Subject(s)
Ageratum , Caenorhabditis elegans , Oils, Volatile , Seasons , Animals , Oils, Volatile/pharmacology , Oils, Volatile/chemistry , Caenorhabditis elegans/drug effects , Caenorhabditis elegans/physiology , Ageratum/chemistry , Antinematodal Agents/pharmacology , Antinematodal Agents/chemistry , Circadian Rhythm/drug effects , Gas Chromatography-Mass Spectrometry
6.
J Agric Food Chem ; 72(17): 9746-9754, 2024 May 01.
Article in English | MEDLINE | ID: mdl-38602331

ABSTRACT

The latex of Euphorbia peplus and its major component 20-deoxyingenol-3-angelate (DI3A) displayed significant nematicidal activity against Caenorhabditis elegans and Panagrellus redivivus. DI3A treatment inhibited the growth and development of nematodes and caused significantly negative effects on locomotion behavior, reproduction, and accumulation of reactive oxygen species. Transcriptome analysis indicated that differential expression genes in DI3A-treated C. elegans were mainly associated with the metabolism, growth, and development process, which were further confirmed by RT-qPCR experiments. The expression level of TPA-1 gene encoding a protein kinase C isotype was obviously upregulated by DI3A treatment, and knockdown of TPA-1 by RNAi technology in the nematode could relieve the growth-inhibitory effect of DI3A. Metabolic analysis indicated that DI3A was hardly metabolized by C. elegans, but a glycosylated indole derivative was specifically accumulated likely due to the activation of detoxification. Overall, our findings suggested that DI3A from E. peplus latex exerted a potent nematicidal effect through the gene TPA-1, which provides a potential target for the control of nematodes and also suggests the potential application value of E. peplus latex and DI3A as botanical nematicides.


Subject(s)
Antinematodal Agents , Caenorhabditis elegans , Euphorbia , Latex , Protein Kinase C , Animals , Caenorhabditis elegans/drug effects , Caenorhabditis elegans/genetics , Caenorhabditis elegans/enzymology , Caenorhabditis elegans/metabolism , Caenorhabditis elegans/growth & development , Latex/chemistry , Latex/metabolism , Antinematodal Agents/pharmacology , Antinematodal Agents/chemistry , Antinematodal Agents/metabolism , Euphorbia/chemistry , Protein Kinase C/metabolism , Protein Kinase C/genetics , Plant Extracts/pharmacology , Plant Extracts/chemistry
7.
J Invertebr Pathol ; 204: 108114, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38636720

ABSTRACT

Agricultural Productivity and plant health are threatened by the root-knot nematode. The use of biocontrol agents reduces the need for chemical nematicides and improves the general health of agricultural ecosystems by offering a more environmentally friendly and sustainable method of managing nematode infestations. Plant-parasitic nematodes can be efficiently managed with the use of entomopathogenic nematodes (EPNs), which are widely used biocontrol agents. This study focused on the nematicidal activity of the secondary metabolites present in the bacteria Ochrobactrum sp. identified in the EPN, Heterorhabditisindica against Root-Knot Nematode (Meloidogyne incognita). Its effect on egg hatching and survival of juveniles of root- knot nematode (RKN) was examined. The ethyl acetate component of the cell-free culture (CFC) filtrate of the Ochrobactrum sp. bacteria was tested at four different concentrations (25 %, 50 %, 75 % and 100 %) along with broth and distilled water as control. The bioactive compounds of Ochrobactrum sp. bacteria showed the highest suppression of M. incognita egg hatching (100 %) and juvenile mortality (100 %) at 100 % concentration within 24 h of incubation. In this study, unique metabolite compounds were identified through the Gas Chromatography- Mass Spectrometry (GC-MS) analysis, which were found to have anti- nematicidal activity. In light of this, molecular docking studies were conducted to determine the impact of biomolecules from Ochrobactrum sp. using significant proteins of M. incognita, such as calreticulin, sterol carrier protein 2, flavin-containing monooxygenase, pectate lyase, candidate secreted effector, oesophageal gland cell secretory protein and venom allergen-like protein. The results also showed that the biomolecules from Ochrobactrum sp. had a significant inhibitory effect on the different protein targets of M. incognita. 3-Epimacronine and Heraclenin were found to inhibit most of the chosen target protein. Among the targets, the docking analysis revealed that Heraclenin exhibited the highest binding affinity of -8.6 Kcal/mol with the target flavin- containing monooxygenase. Further, the in vitro evaluation of 3- Epimacronine confirmed their nematicidal activity against M. incognita at different concentrations. In light of this, the present study has raised awareness of the unique biomolecules of the bacterial symbiont Ochrobactrum sp. isolated from H. indica that have nematicidal properties.


Subject(s)
Molecular Docking Simulation , Ochrobactrum , Tylenchoidea , Animals , Ochrobactrum/metabolism , Antinematodal Agents/pharmacology , Antinematodal Agents/metabolism , Antinematodal Agents/chemistry , Pest Control, Biological
8.
J Agric Food Chem ; 72(11): 5585-5594, 2024 Mar 20.
Article in English | MEDLINE | ID: mdl-38442026

ABSTRACT

To find novel nematicides, we screened the nematicidal activity of compounds in our laboratory compound library. Interestingly, the compound N-((1R,2R)-2-(2-fluoro-4-(trifluoromethyl)phenyl)cyclopropyl)-2-(trifluoromethyl)benzamide (W3) showed a broad spectrum and excellent nematicidal activity. The LC50 values of compound W3 against second-stage juveniles of Bursaphelenchus xylophilus (B. xylophilus), Aphelenchoides besseyi, and Ditylenchus destructor are 1.30, 1.63, and 0.72 mg/L, respectively. Nematicidal activities of compound W3 against second-stage juveniles of Meloidogyne incognita were 87.66% at 100 mg/L. Meanwhile, compound W3 can not only observably inhibit the feeding, reproduction, and egg hatching of B. xylophilus but can also effectively promote the oxidative stress adverse reactions of nematodes and cause intestinal damage. Compound W3 can promote the production of MDA and inhibit the activities of defense enzymes SOD and GST in B. xylophilus. Compound W3 can affect the transcription of genes involved in regulating the tricarboxylic acid cycle in nematodes, resulting in weakened nematode respiration and reduced nematode activity and even death. In addition, compound W3 had good inhibitory activity against five pathogenic fungi. Among them, the EC50 of compound W3 against Fusarium graminearum was 8.4 mg/L. In the future, we will devote ourselves to the toxicological and structural optimization research of the candidate nematicide W3.


Subject(s)
Tylenchida , Tylenchoidea , Animals , Amides/pharmacology , Antinematodal Agents/pharmacology , Antinematodal Agents/chemistry , Reproduction
9.
J Agric Food Chem ; 72(3): 1429-1443, 2024 Jan 24.
Article in English | MEDLINE | ID: mdl-38189665

ABSTRACT

Plant-parasitic nematodes are one of the major threats to crop protection. However, only limited nematicides are currently available and are confronted with a growing resistance problem, which necessitates the development of novel nematicides. In this study, a series of trifluorobutene amide derivatives was synthesized through the strategy of amide bond reversal, and their nematicidal activity against Meloidogyne incognita was evaluated. The bioassay showed that compounds C2, C10, and C18 and some analogues thereof exhibited good nematicidal activity. Among them, the derivatives of compound C2 containing a benzene ring [C26 (R = 2-CH3) and C33 (R = 2-Cl)] exhibited excellent bioactivity against M. incognita in vitro. The LC50/72h values reached 14.13 and 14.71 mg·L-1, respectively. Moreover, analogues of compounds C10 and C18 containing a thiophene ring [C43 (R = 5-CH3), C44 (R = 4-CH3), and C50 (R = 5-Cl)] exhibited significant bioactivity against M. incognita in vivo with inhibition rates of 68.8, 65.5, and 69.8% at 2.5 mg·L-1 in a matrix, respectively. Meanwhile, C44 and C50 also showed excellent control effects against M. incognita in both cups and microplots. The structure-activity relationship (SAR) of synthesized compounds was discussed in detail. Comparative molecular field analysis (CoMFA) was also conducted to develop the SAR profile. The preliminary mode of action investigation showed that compound C33 exhibited strong inhibition on egg hatching, motility, feeding behavior, and growth of Caenorhabditis elegans. At the same time, the impact of active compounds on biochemical indicators related to oxidative stress showed that compound C33 influenced the production of ROS (reactive oxygen species), and the accumulation of lipofuscin and lipids on C. elegans.


Subject(s)
Tylenchida , Tylenchoidea , Animals , Amides/pharmacology , Caenorhabditis elegans , Antinematodal Agents/chemistry , Structure-Activity Relationship
10.
J Agric Food Chem ; 72(5): 2473-2481, 2024 Feb 07.
Article in English | MEDLINE | ID: mdl-38284538

ABSTRACT

Bursaphelenchus xylophilus (B. xylophilus) and Meloidogyne are parasitic nematodes that have caused severe ecological and economic damage in pinewood and crops, respectively. Jietacins (jietacin A and B) were found to have excellent biological activity against B. xylophilus. Based on our tremendous demand for chemicals against B. xylophilus, a novel scaffold based on the azo and azoxy groups was designed, and a series of compounds were synthesized. In the bioassay, Ia, IIa, IIc, IId, and IVa exhibited higher activity against B. xylophilus in vitro than avermectin (LC50 = 2.43 µg·mL-1) with LC50 values of 1.37, 1.12, 0.889, 1.56, and 1.10 µg·mL-1, respectively. Meanwhile, Ib, Ic, IIc, and IVa showed good inhibition effects against Meloidogyne in vivo at the concentrations of 80 and 40 µg·mL-1 with inhibition rates of 89.0% and 81.6%, 95.6% and 75.7%, 96.3% and 41.2%, and 86.8% and 78.7%, respectively. In fungicidal activity in vitro, IIb and IVa exhibited excellent effect against Botryosphaeria dothidea with the inhibition of 82.59% and 85.32% at the concentration of 10 µg·mL-1, while the inhibition of Ia was 83.16% against Rhizoctonia solani at the concentration of 12.5 µg·mL-1. Referring to the biological activity against B. xylophilus, a 3D-QASR model was built in which the electron-donating group and small group at the 4-phenylhydrazine were favorable for the activity. In general, the novel azoxy compounds, especially IIc possess great potential for application in the prevention of B. xylophilus.


Subject(s)
Pinus , Tylenchida , Tylenchoidea , Animals , Antinematodal Agents/chemistry , Pinus/parasitology
11.
J Agric Food Chem ; 72(5): 2482-2491, 2024 Feb 07.
Article in English | MEDLINE | ID: mdl-38264997

ABSTRACT

In a previously published study, the authors devised a molecular topology QSAR (quantitative structure-activity relationship) approach to detect novel fungicides acting as inhibitors of chitin deacetylase (CDA). Several of the chosen compounds exhibited noteworthy activity. Due to the close relationship between chitin-related proteins present in fungi and other chitin-containing plant-parasitic species, the authors decided to test these molecules against nematodes, based on their negative impact on agriculture. From an overall of 20 fungal CDA inhibitors, six showed to be active against Caenorhabditis elegans. These experimental results made it possible to develop two new molecular topology-based QSAR algorithms for the rational design of potential nematicides with CDA inhibitor activity for crop protection. Linear discriminant analysis was employed to create the two algorithms, one for identifying the chemo-mathematical pattern of commercial nematicides and the other for identifying nematicides with activity on CDA. After creating and validating the QSAR models, the authors screened several natural and synthetic compound databases, searching for alternatives to current nematicides. Finally one compound, the N2-(dimethylsulfamoyl)-N-{2-[(2-methyl-2-propanyl)sulfanyl]ethyl}-N2-phenylglycinamide or nematode chitin deacetylase inhibitor, was selected as the best candidate and was further investigated both in silico, through molecular docking and molecular dynamic simulations, and in vitro, through specific experimental assays. The molecule shows favorable binding behavior on the catalytic pocket of C. elegans CDA and the experimental assays confirm potential nematicide activity.


Subject(s)
Amidohydrolases , Caenorhabditis elegans , Nematoda , Animals , Caenorhabditis elegans/metabolism , Molecular Docking Simulation , Antinematodal Agents/chemistry , Chitin/metabolism
12.
PLoS One ; 18(8): e0289935, 2023.
Article in English | MEDLINE | ID: mdl-37585451

ABSTRACT

Root-knot nematodes (Meloidogyne spp.) are dangerous parasites of many crops worldwide. The threat of chemical nematicides has led to increasing interest in studying the inhibitory effects of organic amendments and bacteria on plant-parasitic nematodes, but their combination has been less studied. One laboratory and four glasshouse experiments were conducted to study the effect on M. javanica of animal manure, common vermicompost, shrimp shells, chitosan, compost and vermicompost from castor bean, chinaberry and arugula, and the combination of arugula vermicompost with some bacteria, isolated from vermicompost or earthworms. The extract of arugula compost and vermicompost, common vermicompost and composts from castor bean and chinaberry reduced nematode egg hatch by 12-32% and caused 13-40% mortality of second-stage juveniles in vitro. Soil amendments with the combination vermicompost of arugula + Pseudomonas. resinovorans + Sphingobacterium daejeonense + chitosan significantly increased the yield of infected tomato plants and reduced nematode reproduction factor by 63.1-76.6%. Comparison of chemical properties showed that arugula vermicompost had lower pH, EC, and C/N ratio than arugula compost. Metagenomics analysis showed that Bacillus, Geodermatophilus, Thermomonas, Lewinella, Pseudolabrys and Erythrobacter were the major bacterial genera in the vermicompost of arugula. Metagenomics analysis confirmed the presence of chitinolytic, detoxifying and PGPR bacteria in the vermicompost of arugula. The combination of arugula vermicompost + chitosan + P. resinovorans + S. daejeonense could be an environmentally friendly approach to control M. javanica.


Subject(s)
Bacillus , Chitosan , Ricinus communis , Tylenchoidea , Animals , Chitin , Chitosan/pharmacology , Antinematodal Agents/pharmacology , Antinematodal Agents/chemistry
13.
Plant Dis ; 107(8): 2352-2358, 2023 Aug.
Article in English | MEDLINE | ID: mdl-37552644

ABSTRACT

The demand for new soil fumigants has increased as a result of more restrictive legislation regarding the use of pesticides. In the present study, the potent nematicidal activity of volatile organic compounds released by the Annona muricata leaf macerate was demonstrated. In addition, we searched in the A. muricata volatilome for a molecule with potential to be developed as a new fumigant nematicide. In the greenhouse, even the lowest concentration of soursop leaf macerate tested (1.0%) as a biofumigant caused a significant (P < 0.05) reduction in Meloidogyne incognita infectivity and reproduction when compared with the nontreated control (0%). Forty-one compounds were identified through gas chromatography-mass spectrometry analysis, of which three (sabinene, caryophyllene oxide, and 4-ethylbenzaldehyde) were selected for studies against the nematode. Among these compounds, in in vitro trails, only 4-ethylbenzaldehyde showed nematicidal activity at 250 µg ml-1. The effective doses of 4-ethylbenzaldehyde predicted to kill 50 and 95% of the M. incognita second-stage juvenile population after 48 h of exposure were 35 and 88 µg ml-1, respectively. In in vitro tests, 4-ethylbenzaldehyde at 150 µg ml-1 reduced M. incognita egg hatching to values similar (P > 0.05) to those of the commercial nematicide fluensulfone at a concentration of 200 µg ml-1. In plant experiments, as a soil fumigant, 4-ethylbenzaldehyde at a dose of 1 ml/liter of substrate had an effect similar (P > 0.05) to that of the commercial fumigant Dazomet (250 µg ml-1). Therefore, 4-ethylbenzaldehyde shows potential for development as a new nematicide.


Subject(s)
Annona , Pesticides , Tylenchoidea , Animals , Antinematodal Agents/pharmacology , Antinematodal Agents/chemistry , Pesticides/pharmacology , Soil/chemistry
14.
J Helminthol ; 97: e60, 2023 Jul 26.
Article in English | MEDLINE | ID: mdl-37492936

ABSTRACT

The nematicidal activity of buckwheat (Fagopyrum esculentum Moench) on the root-knot nematode Meloidogyne incognita was tested. Dried plant methanol extract presented higher nematicidal activity than fresh plant extracts with an EC50 = 62.6 ± 26.0 and 40.8 ± 26.1 µg/ml after 48 and 72 hours of immersion, respectively. GC-MS analysis showed the presence of 17 aldehydes, with salicylaldehyde (o-hydroxybenzaldehyde) being the most abundant at 16%. Nematicidal activity of the latter refers to salicylaldehyde and other aldehydes with chemical similarities was then assessed. The most active aldehyde was o-hydroxybenzaldehyde followed by m-hydroxybenzaldehyde, p-hydroxybenzaldehyde and benzeneacetaldehyde with an EC50 of about 11.0 ± 1.0, 31.0 ± 22.0, 75.0 ± 23.0 and 168.1 ± 52.3 µg/ml after 1 day of immersion, respectively. Position 2 of the hydroxyl group in the benzene ring seems to be very important for the nematicidal activity, followed by positions 3 and 4. As a complementary experiment, synergistic activity was observed when we added o-hydroxybenzaldehyde to m-hydroxybenzaldehyde and to p-hydroxybenzaldehyde with an EC50 after 24 hours of immersion of 8.0 ± 2.5 and 6.1 ± 2.3 µg/ml, respectively. Antioxidant activity assessment showed that this latter is inversely proportional to nematicidal activity. Our results showed that F. esculentum and its major compound salicylaldehyde could be integrated into the pest management system.


Subject(s)
Fagopyrum , Tylenchoidea , Animals , Methanol , Antinematodal Agents/pharmacology , Antinematodal Agents/chemistry , Aldehydes/pharmacology , Aldehydes/chemistry , Plant Extracts/pharmacology , Plant Extracts/chemistry
15.
Molecules ; 28(11)2023 May 26.
Article in English | MEDLINE | ID: mdl-37298840

ABSTRACT

Plant parasitic nematodes (PPNs) are highly destructive and difficult to control, while conventional chemical nematicides are highly toxic and cause serious environmental pollution. Additionally, resistance to existing pesticides is becoming increasingly common. Biological control is the most promising method for the controlling of PPNs. Therefore, the screening of nematicidal microbial resources and the identification of natural products are of great significance and urgency for the environmentally friendly control of PPNs. In this study, the DT10 strain was isolated from wild moss samples and identified as Streptomyces sp. by morphological and molecular analysis. Using Caenorhabditis elegans as a model, the extract of DT10 was screened for nematicidal activity, which elicited 100% lethality. The active compound was isolated from the extracts of strain DT10 using silica gel column chromatography and semipreparative high-performance liquid chromatography (HPLC). The compound was identified as spectinabilin (chemical formula C28H31O6N) using liquid chromatography mass spectrometry (LC-MS) and nuclear magnetic resonance (NMR). Spectinabilin exhibited a good nematicidal activity on C. elegans L1 worms, with a half-maximal inhibitory concentration (IC50) of 2.948 µg/mL at 24 h. The locomotive ability of C. elegans L4 worms was significantly reduced when treated with 40 µg/mL spectinabilin. Further analysis of spectinabilin against known nematicidal drug target genes in C. elegans showed that it acts via target(s) different from those of some currently used nematicidal drugs such as avermectin and phosphine thiazole. This is the first report on the nematicidal activity of spectinabilin on C. elegans and the southern root-knot nematode Meloidogyne incognita. These findings may pave the way for further research and application of spectinabilin as a potential biological nematicide.


Subject(s)
Streptomyces , Tylenchoidea , Animals , Caenorhabditis elegans , Antinematodal Agents/pharmacology , Antinematodal Agents/chemistry
16.
J Agric Food Chem ; 71(23): 8757-8768, 2023 Jun 14.
Article in English | MEDLINE | ID: mdl-37277310

ABSTRACT

Plant-parasitic nematodes (PPNs) are one of the major threats to modern agriculture. Chemical nematicides are still required for the management of PPNs. Based on our previous work, the structure of aurone analogues was obtained using a hybrid 3D similarity calculation method (SHAFTS, SHApe-FeaTure Similarity). Thirty-seven compounds were synthesized. The nematicidal activity of target compounds against Meloidogyne incognita (root-knot nematode, M. incognita) was evaluated, and the structure-activity relationship of synthesized compounds was analyzed. The results showed that compound 6 and some of its derivatives exhibited impressive nematicidal activity. Among these compounds, compound 32 bearing 6-F showed the best in vitro and in vivo nematicidal activity. Its lethal concentration 50% after exposure to 72 h (LC50/72 h) value was 1.75 mg/L, and the inhibition rate reached 97.93% in the sand at 40 mg/L. At the same time, compound 32 also exhibited excellent inhibition on egg hatching and moderate inhibition on the motility of Caenorhabditis elegans (C. elegans).


Subject(s)
Benzofurans , Tylenchoidea , Animals , Caenorhabditis elegans , Antinematodal Agents/chemistry , Structure-Activity Relationship , Benzofurans/pharmacology
17.
Nature ; 618(7963): 102-109, 2023 Jun.
Article in English | MEDLINE | ID: mdl-37225985

ABSTRACT

Parasitic nematodes are a major threat to global food security, particularly as the world amasses 10 billion people amid limited arable land1-4. Most traditional nematicides have been banned owing to poor nematode selectivity, leaving farmers with inadequate means of pest control4-12. Here we use the model nematode Caenorhabditis elegans to identify a family of selective imidazothiazole nematicides, called selectivins, that undergo cytochrome-p450-mediated bioactivation in nematodes. At low parts-per-million concentrations, selectivins perform comparably well with commercial nematicides to control root infection by Meloidogyne incognita, a highly destructive plant-parasitic nematode. Tests against numerous phylogenetically diverse non-target systems demonstrate that selectivins are more nematode-selective than most marketed nematicides. Selectivins are first-in-class bioactivated nematode controls that provide efficacy and nematode selectivity.


Subject(s)
Antinematodal Agents , Tylenchoidea , Animals , Humans , Antinematodal Agents/chemistry , Antinematodal Agents/metabolism , Antinematodal Agents/pharmacology , Caenorhabditis elegans/drug effects , Caenorhabditis elegans/metabolism , Tylenchoidea/drug effects , Tylenchoidea/metabolism , Thiazoles/chemistry , Thiazoles/metabolism , Thiazoles/pharmacology , Cytochrome P-450 Enzyme System/drug effects , Plant Roots/drug effects , Plant Roots/parasitology , Plant Diseases , Species Specificity , Substrate Specificity
18.
Molecules ; 28(10)2023 May 15.
Article in English | MEDLINE | ID: mdl-37241850

ABSTRACT

Pine wood nematode (PWN), Bursaphelenchus xylophilus, is a major pathogen of pine wilt disease (PWD), which is a devastating disease affecting pine trees. Eco-friendly plant-derived nematicides against PWN have been considered as promising alternatives to control PWD. In this study, the ethyl acetate extracts of Cnidium monnieri fruits and Angelica dahurica roots were confirmed to have significant nematicidal activity against PWN. Through bioassay-guided fractionations, eight nematicidal coumarins against PWN were separately isolated from the ethyl acetate extracts of C. monnieri fruits and A. dahurica roots, and they were identified to be osthol (Compound 1), xanthotoxin (Compound 2), cindimine (Compound 3), isopimpinellin (Compound 4), marmesin (Compound 5), isoimperatorin (Compound 6), imperatorin (Compound 7), and bergapten (Compound 8) by mass and nuclear magnetic resonance (NMR) spectral data analysis. Coumarins 1-8 were all determined to have inhibitory effects on the egg hatching, feeding ability, and reproduction of PWN. Moreover, all eight nematicidal coumarins could inhibit the acetylcholinesterase (AChE) and Ca2+ ATPase of PWN. Cindimine 3 from C. monnieri fruits showed the strongest nematicidal activity against PWN, with an LC50 value of 64 µM at 72 h, and the highest inhibitory effect on PWN vitality. In addition, bioassays on PWN pathogenicity demonstrated that the eight nematicidal coumarins could effectively relieve the wilt symptoms of black pine seedlings infected by PWN. The research identified several potent botanical nematicidal coumarins for use against PWN, which could contribute to the development of greener nematicides for PWD control.


Subject(s)
Angelica , Nematoda , Pinus , Tylenchida , Animals , Cnidium , Xylophilus , Acetylcholinesterase/pharmacology , Fruit , Antinematodal Agents/pharmacology , Antinematodal Agents/chemistry , Coumarins/pharmacology , Plant Diseases
19.
Molecules ; 28(7)2023 04 03.
Article in English | MEDLINE | ID: mdl-37049944

ABSTRACT

The Bacillus velezensis GJ-7 strain isolated from the rhizosphere soil of Panax notoginseng showed high nematicidal activity and therefore has been considered a biological control agent that could act against the root-knot nematode Meloidogyne hapla. However, little was known about whether the GJ-7 strain could produce volatile organic compounds (VOCs) that were effective in biocontrol against M. hapla. In this study, we evaluated the nematicidal activity of VOCs produced by the fermentation of GJ-7 in three-compartment Petri dishes. The results revealed that the mortality rates of M. hapla J2s were 85% at 24 h and 97.1% at 48 h after treatment with the VOCs produced during GJ-7 fermentation. Subsequently, the VOCs produced by the GJ-7 strain were identified through solid-phase micro-extraction gas chromatography mass spectrometry (SPME-GC/MS). Six characteristic VOCs from the GJ-7 strain fermentation broth were identified, including 3-methyl-1-butanol, 3-methyl-2-pentanone, 5-methyl-2-hexanone, 2-heptanone, 2,5-dimethylpyrazine, and 6-methyl-2-heptanone. The in vitro experimental results from 24-well culture plates showed that the six volatiles had direct-contact nematicidal activity against M. hapla J2s and inhibition activity against egg hatching. In addition, 3-methyl-1-butanol and 2-heptanone showed significant fumigation effects on M. hapla J2s and eggs. Furthermore, all six of the VOCs repelled M. hapla J2 juveniles in 2% water agar Petri plates. The above data suggested that the VOCs of B. velezensis GJ-7 acted against M. hapla through multiple prevention and control modes (including direct-contact nematicidal activity, fumigant activity, and repellent activity), and therefore could be considered as potential biocontrol agents against root-knot nematodes.


Subject(s)
Tylenchoidea , Volatile Organic Compounds , Animals , Volatile Organic Compounds/chemistry , Antinematodal Agents/pharmacology , Antinematodal Agents/chemistry
20.
Carbohydr Polym ; 306: 120592, 2023 Apr 15.
Article in English | MEDLINE | ID: mdl-36746583

ABSTRACT

Chemical nematicide is the most common method of controlling plant-parasitic nematodes (PPN). Given the negative impact of chemical nematicides on the environment and ecosystem, it is necessary to seek their alternatives and novel modes of application. Chitin oligo/polysaccharide (COPS), including chitosan and chitosan oligosaccharide, has unique biological properties. By producing ammonia, encouraging the growth of antagonistic bacteria, and enhancing crop tolerance, COPSs help suppress PPN growth during soil remediation. COPS is also an effective sustained-release carrier that can be used to overcome the shortcomings of nematicidal substances. This review summarizes the advancements of COPS research in nematode control from three perspectives of action mechanism as well as in slow-release carrier-loaded nematicides. Further, it discusses potential agricultural applications for nematode disease management.


Subject(s)
Chitosan , Nematoda , Animals , Chitin/pharmacology , Chitin/chemistry , Chitosan/pharmacology , Chitosan/chemistry , Ecosystem , Agriculture , Antinematodal Agents/pharmacology , Antinematodal Agents/chemistry , Oligosaccharides/pharmacology
SELECTION OF CITATIONS
SEARCH DETAIL