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Journal of Agricultural and Food... Jun 2023Falcarindiol is active against phytopathogenic fungi. In the present study, racemic falcarindiol analogs (-) were designed, synthesized, and tested for their activities...
Falcarindiol is active against phytopathogenic fungi. In the present study, racemic falcarindiol analogs (-) were designed, synthesized, and tested for their activities against eight economically significant phytopathogenic fungal species. The compound displayed the best antifungal activities and up to 54.6-fold in vitro potency improvement against than the natural product stipudiol. Its half-maximum effective concentrations ranged from 4 to 23 μg/mL against all tested fungal species. Racemic was 195-fold more potent than the fungicide carbendazim against in vitro. The isomer (1, 6) exhibited an EC of 1.10 and 2.70 μg/mL against and , respectively, which was 47 and 11 times lower than (1, 6)- and (1, 6). In addition, in vivo bioassay results showed that (1, 6)- had high antifungal activity against infection of and to apricot and pepper fruits and pepper plants, which the efficacy was similar or better than carbendazim. The high potency and selectivity of stereoisomers against the phytopathogens warrant an interest in elucidating the molecular target for fungicide development.
Topics: Antifungal Agents; Fungicides, Industrial; Polyacetylene Polymer; Stereoisomerism; Polyynes; Fungi; Structure-Activity Relationship
PubMed: 37261403
DOI: 10.1021/acs.jafc.3c00924 -
Journal of Fungi (Basel, Switzerland) Sep 2022Rice blast caused by Magnaporthe oryzae is one of the most destructive fungal diseases of rice worldwide. Stimulatory effects of low doses of fungicides on pathogens are...
Rice blast caused by Magnaporthe oryzae is one of the most destructive fungal diseases of rice worldwide. Stimulatory effects of low doses of fungicides on pathogens are closely relevant to disease management. In the present study, in potato dextrose agar (PDA) amended with carbendazim at a dose range from 0.003 to 0.3 μg/mL, stimulatory effects on the mycelial growth of three isolates sensitive to carbendazim were tested. Carbendazim at concentrations from 0.003 to 0.1 µg/mL showed stimulatory effects on mycelial growth of isolates Guy11 and H08-1a, while carbendazim at concentrations from 0.003 to 0.03 µg/mL stimulated the growth of isolate P131. The maximum stimulation magnitudes were 11.84% for the three isolates tested. Mycelial colonies grown on PDA amended with different concentrations of carbendazim were incubated at 28 °C in darkness for 7 days as the pretreatment. Pretreatment mycelia were inoculated on fresh fungicide-free PDA and subsequent mycelia growth stimulations were still observed, and the maximum stimulation magnitudes were 9.15% for the three isolates tested. Pretreatment mycelia did not significantly change the tolerance to H2O2 and NaCl, except that the tolerance to H2O2 was increased significantly (p < 0.05) when the carbendazim was at 0.3 µg/mL. After five generations of mycelial transference on fungicide-free PDA, the transgenerational hormesis of mycelial were exhibited when transferred onto PDA supplemented with carbendazim at 0.3 µg/mL, and the maximum percent stimulation was 51.28%. The time course of infection indicated that the visible initial necrotic symptoms could be detected at 2 DPI on leaves treated with carbendazim at 0.03 µg/mL, whereas no necrotic symptom could be discerned for the control. Statistical results of lesion area and lesion type at 7 DPI showed that there was a significant stimulation (p < 0.05) on aggressiveness of M. oryzae isolate Guy11 on detached rice leaves at 0.03 µg/mL carbendazim. These results will advance our understanding of hormetic effects of fungicides and provide valuable information for judicious application of fungicides.
PubMed: 36294573
DOI: 10.3390/jof8101008 -
Analytical Methods : Advancing Methods... Sep 2021Enzyme-linked immunosorbent assay (ELISA) with high specificity and sensitivity is one of the most popular techniques for detecting carbendazim (CBD), a commonly used...
Enzyme-linked immunosorbent assay (ELISA) with high specificity and sensitivity is one of the most popular techniques for detecting carbendazim (CBD), a commonly used benzimidazole fungicide in agriculture. However, the traditional ELISA based on the horseradish peroxidase (HRP)-3,3',5,5'-tetramethylbenzidine (TMB) system for CBD only displays the yellow color of TMB from deep to light, making it difficult for the naked eye to judge whether CBD in fruits and vegetables exceeds the maximum residue limit. In this article, we intend to improve the traditional ELISA method to establish a multicolor signal output ELISA to achieve visual semiquantitative detection of CBD. This method is based on the optical properties of gold nanorods (AuNRs). After introducing AuNRs into TMB solution, which was produced by the HRP-TMB system of traditional ELISA, AuNRs were quickly etched by TMB. Consequently, the longitudinal localized surface plasmon resonance peak of AuNRs shows a clear blue shift and a vivid color change. Different concentrations of CBD generate different amounts of TMB, which in turn leads to different etching degrees of AuNRs, and ultimately results in a rainbow-like color change. As a result, CBD from 0.08 to 100 ng mL can be easily distinguished by the naked eye, which does not require any large instruments. Moreover, the colors displayed by 0.49 ng mL (purple) and 0 ng mL (pink) are significantly different from each other. It should be noted that 0.49 ng mL is far below the most stringent maximum residue limit of CBD in the world. Additionally, the quantitative determination of CBD spiked in canned citrus, citrus fruits, chives, and cabbage samples showed satisfactory recoveries. The good performance of the AuNR-based ELISA makes it have a wide range of application prospects in food safety and international trade.
Topics: Benzimidazoles; Biosensing Techniques; Carbamates; Commerce; Enzyme-Linked Immunosorbent Assay; Internationality
PubMed: 34591948
DOI: 10.1039/d1ay01028j -
Toxics Nov 2023The world population is experiencing colossal growth and thus demand for food, leading to an increase in the use of pesticides. Persistent pesticide contamination, such...
The world population is experiencing colossal growth and thus demand for food, leading to an increase in the use of pesticides. Persistent pesticide contamination, such as carbendazim, remains a pressing environmental concern, with potentially long-term impacts on aquatic ecosystems. In the present study, was exposed to carbendazim (5 µg L) for 12 generations, with the aim of assessing gene transcription alterations induced by carbendazim (using a custom microarray). The results showed that carbendazim caused changes in genes involved in the response to stress, DNA replication/repair, neurotransmission, ATP production, and lipid and carbohydrate metabolism at concentrations already found in the environment. These outcomes support the results of previous studies, in which carbendazim induced genotoxic effects and reproduction impairment (increasing the number of aborted eggs with the decreasing number of neonates produced). The exposure of daphnids to carbendazim did not cause a stable change in gene transcription between generations, with more genes being differentially expressed in the F0 generation than in the F12 generation. This could show some possible daphnid acclimation after 12 generations and is aligned with previous multigenerational studies where few ecotoxicological effects at the individual and populational levels and other subcellular level effects (e.g., biochemical biomarkers) were found.
PubMed: 37999570
DOI: 10.3390/toxics11110918 -
Environmental Pollution (Barking, Essex... Jan 2023A sensitive and stable substrate plays a vital role in the Raman spectroscopic techniques as an analytical method for detecting pesticides effectively from the...
A sensitive and stable substrate plays a vital role in the Raman spectroscopic techniques as an analytical method for detecting pesticides effectively from the environment. Enhancing signals from nanoparticles are weak and inconsistent in repeatability since analytes tend to degrade quickly under laser exposure. Herein, a novel substrate of Au@ZIF-67 is prepared on octahedral AuNPs by trapping pesticide molecules with small three-dimensional volumes by the flexibility of ZIF-67 for rapid detection with high sensitivity and stability. The two types of thiram and carbendazim pesticides, which are environmental pollutants that affect biodiversity, were successfully absorbed in Au@ZIF-67 nanostructures by adsorption-desorption equilibrium for analytical purposes in Raman spectroscopy. Spectra calculations of the thiram and carbendazim molecules on 8 atoms of Au using DFT were compared with the experimental data. The SERS enhancement factors for thiram and carbendazim were estimated to be 1.91 × 10 and 3.12 × 10, respectively, with the LOD values of trace amounts of ∼10 mol L. The novel substrate of Au@ZIF-67 is a propitious platform for detecting thiram and carbendazim in trace amounts, providing a helpful strategy for detecting residues with high performance in the environment at the laboratory and practical scales.
Topics: Pesticides; Thiram; Environmental Pollutants; Gold; Metal Nanoparticles; Spectrum Analysis, Raman
PubMed: 36455771
DOI: 10.1016/j.envpol.2022.120775 -
Food Chemistry Dec 2022Extensively employed pesticide in agriculture causes residue in food products that would threaten public health safety. The surface-enhanced Raman scattering (SERS)...
Extensively employed pesticide in agriculture causes residue in food products that would threaten public health safety. The surface-enhanced Raman scattering (SERS) signal reliant on double sensing of carbendazim and thiabendazole in a single step is achieved without the aid of any bio-recognition element. A label-free anisotropic bimetallic hollow Au/Ag nanostars (HAu/Ag NS) SERS substrate was synthesized with numerous hot spots for Raman molecule through a galvanic displacement-free deposition. The individual and mixed analyte calibration results were compared based on the identified peak at 1224 (carbendazim) and 778 (thiabendazole) cm and exhibited insignificant differences. The sensor could detect carbendazim and thiabendazole up to 4.28 × 10 and 6.04 × 10 µg·g or µg·mL in both individual and mixture of their extract. The recovery for accuracy and precision analysis was 91.54-98.26 % in rice and water. Finally, validation results were achieved satisfactorily (p > 0.05) with HPLC.
Topics: Benzimidazoles; Fungicides, Industrial; Gold; Metal Nanoparticles; Silver; Spectrum Analysis, Raman; Thiabendazole
PubMed: 35901616
DOI: 10.1016/j.foodchem.2022.133755 -
Water Research Apr 2023Co-pollution of soil with pesticide residues and antibiotic resistance genes (ARGs) is increasing due to the substantial usage of pesticides and organic fertilizers in...
Co-pollution of soil with pesticide residues and antibiotic resistance genes (ARGs) is increasing due to the substantial usage of pesticides and organic fertilizers in greenhouse-based agricultural production. Non-antibiotic stresses, including those from agricultural fungicides, are potential co-selectors for the horizontal transfer of ARGs, but the underlying mechanism remains unclear. Intragenus and intergenus conjugative transfer systems of the antibiotic resistant plasmid RP4 were established to examine conjugative transfer frequency under stress from four widely used fungicides: triadimefon, chlorothalonil, azoxystrobin, and carbendazim. The mechanisms were elucidated at the cellular and molecular levels using transmission electron microscopy, flow cytometry, RT-qPCR, and RNA-seq techniques. The conjugative transfer frequency of plasmid RP4 between Escherichia coli strains increased with the rising exposure concentrations of chlorothalonil, azoxystrobin, and carbendazim, but was suppressed between E. coli and Pseudomonas putida by a high fungicide concentration (10 µg/mL). Triadimefon did not significantly affect conjugative transfer frequency. Exploration of the underlying mechanisms revealed that: (i) chlorothalonil exposure mainly promoted generation of intracellular reactive oxygen species, stimulated the SOS response, and increased cell membrane permeability, while (ii) azoxystrobin and carbendazim primarily enhanced expression of conjugation-related genes on the plasmid. These findings reveal the fungicide-triggered mechanisms associated with plasmid conjugation and highlight the potential role of non-bactericidal pesticides on the dissemination of ARGs.
Topics: Anti-Bacterial Agents; Escherichia coli; Fungicides, Industrial; Genes, Bacterial; Drug Resistance, Microbial; Plasmids; Gene Transfer, Horizontal
PubMed: 36863279
DOI: 10.1016/j.watres.2023.119789 -
Analytical Chemistry Jan 2023Pressure has been a facile signal readout mode for developing point-of-care testing devices due to the attractive features of portability, accessibility, rapidity, and...
Pressure has been a facile signal readout mode for developing point-of-care testing devices due to the attractive features of portability, accessibility, rapidity, and affordability. Herein, a pressure signal readout device was designed by integrating two homemade needle-type piezoresistive transducers, a controller for a thin-film piezoresistive sensor and a smartphone. Meanwhile, a bidirectional immunochromatographic test strip was designed as an immunoreaction platform for dual-analyte detection. Using PdCuPt nanoparticles with catalase-mimic activity as signal tags, the pressure signals triggered by catalyzed aerogenous reaction were monitored by the pressure signal readout device and read on a smartphone with the Bluetooth module. In this proof-of-principle work, imidacloprid and carbendazim were detected as model analytes. The dynamic ranges for quantitating imidacloprid and carbendazim are 20 pg mL to 50 ng mL and 50 pg mL to 50 ng mL, respectively. The whole immunoassay process was completed within 16 min. The recovery values for imidacloprid and carbendazim spiked into herbal medicines are 82.0-110.0 and 84.0-116.0%, respectively, verifying its reliability for real sample detection. As the smartphone APP and controller for a thin-film piezoresistive sensor contain 12 signal channels, the system can be easily extended to meet the demand for high-throughput screening.
Topics: Smartphone; Reproducibility of Results; Benzimidazoles; Immunoassay; Limit of Detection
PubMed: 36575992
DOI: 10.1021/acs.analchem.2c04322 -
Journal of Food Protection Oct 2023Dissipation, residue levels, and ingestion risks of carbendazim in peach (Amygdalus persica L.) were investigated with individual and joint applications in the present...
Dissipation, residue levels, and ingestion risks of carbendazim in peach (Amygdalus persica L.) were investigated with individual and joint applications in the present study. The dissipation kinetics of carbendazim, chlorpyrifos, prochloraz, and imidacloprid were evaluated by the first-order kinetics. When carbendazim was individually applied, the final residual concentration was 2.97 mg kg and the half-life was 17.4 d. In the joint application of carbendazim with chlorpyrifos, prochloraz, and imidacloprid, the residual concentrations at 35 d after spraying were 7.16, 7.50, and 4.26 mg kg and the half-lives were 30.8, 23.7, and 23.2 d, respectively, which showed an increase of 1.3-1.8 times compared with the single application of carbendazim. In addition, the effects of household processing of rinsing and peeling were investigated, and a high removal rate of 54.6% and 76.5% were found. Furthermore, the carbendazim ingestion risk assessment was conducted, which indicated that the acute health risk (aHI) and hazard quotient (HQ) of carbendazim were all within acceptable levels ranging from 21.7% to 40.9%. However, a higher ingestion risk of carbendazim was found under the joint application. This study provides some preliminary guidance for the joint application and risk assessment of carbendazim in peach, which is worth further investigation.
Topics: Prunus persica; Chlorpyrifos; Risk Assessment; Pesticide Residues
PubMed: 37604252
DOI: 10.1016/j.jfp.2023.100145 -
Applied and Environmental Microbiology Sep 2021The plant pathogen Fusarium graminearum contains two α-tubulin isotypes (α and α) and two β-tubulin isotypes (β and β). The functional roles of these tubulins in...
The plant pathogen Fusarium graminearum contains two α-tubulin isotypes (α and α) and two β-tubulin isotypes (β and β). The functional roles of these tubulins in microtubule assembly are not clear. Previous studies reported that α- and β-tubulin deletion mutants showed severe growth defects and hypersensitivity to carbendazim, which have not been well explained. Here, we investigated the interaction between α- and β-tubulin of F. graminearum. Colocalization experiments demonstrated that β- and β-tubulin are colocalized. Coimmunoprecipitation experiments suggested that β-tubulin binds to both α- and α-tubulin and that β-tubulin can also bind to α- or α-tubulin. Interestingly, deletion of α-tubulin increased the interaction between β-tubulin and α-tubulin. Microtubule observation assays showed that deletion of α-tubulin completely disrupted β-tubulin-containing microtubules and significantly decreased β-tubulin-containing microtubules. Deletion of α-, β-, or β-tubulin had no obvious effect on the microtubule cytoskeleton. However, microtubules in α- and β-tubulin deletion mutants were easily depolymerized in the presence of carbendazim. The sexual reproduction assay indicates that α- and β-tubulin deletion mutants could not produce asci and ascospores. These results implied that α-tubulin may be essential for the microtubule cytoskeleton. However, our Δα-2×α mutant (α-tubulin deletion mutant containing two copies of α-tubulin) exhibited normal microtubule network, growth, and sexual reproduction. Interestingly, the Δα-2×α mutant was still hypersensitive to carbendazim. In addition, both β-tubulin and β-tubulin were found to bind the mitochondrial outer membrane voltage-dependent anion channel (VDAC), indicating that they could regulate the function of VDAC. In this study, we found that F. graminearum contains four different α-/β-tubulin heterodimers (α-/β-, α-/β-, α-/β-, and α-/β-tubulin heterodimers), and they assemble together into a single microtubule. Moreover, α- and α-tubulins are functionally interchangeable in microtubule assembly, vegetative growth, and sexual reproduction. These results provide more insights into the functional roles of different tubulins of F. graminearum, which could be helpful for purification of tubulin heterodimers and development of new tubulin-binding agents.
Topics: Fungal Proteins; Fusarium; Microtubules; Tubulin; Voltage-Dependent Anion Channels
PubMed: 34378994
DOI: 10.1128/AEM.00967-21