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1.
Org Lett ; 26(11): 2309-2314, 2024 Mar 22.
Artigo em Inglês | MEDLINE | ID: mdl-38466078

RESUMO

2-Alkylpyridines are a privileged scaffold throughout the realm of organic synthesis and play a key role in natural products, pharmaceuticals, and agrochemicals. Herein, we report the first B-alkyl Suzuki cross-coupling of 2-pyridyl ammonium salts to access functionalized 2-alkylpyridines. The use of well-defined, operationally simple Pd-NHCs permits for an exceptionally broad scope of the challenging B-alkyl C-N cross-coupling with organoboranes containing ß-hydrogen, representing a novel method for the discovery of highly sought-after molecules for plant protection.

2.
Pest Manag Sci ; 2024 Feb 23.
Artigo em Inglês | MEDLINE | ID: mdl-38391097

RESUMO

BACKGROUD: Endoplasmic reticulum/sarcoplasmic reticulum (ER/SR) is crucial for maintaining intracellular calcium homeostasis due to the calcium-signaling-related proteins on its membrane. While ryanodine receptors (RyR) on insect ER/SR membranes are well-known as targets for diamide insecticides, little is known about other calcium channels. Given the resistance of diamide insecticides, the establishment of molecular screening models targeting RyR or sarco/endoplasmic reticulum calcium ATPase (SERCA) is conducive to the discovery of new insecticidal molecules. RESULTS: The morphological features of Mythimna separata SR have closed vesicles with integrity and high density. The 282 proteins in the SR component contained RyR and SERCA. A measurement model for the release and uptake of calcium was successfully established by detecting calcium ions outside the SR membrane using a fluorescence spectrophotometer. In vitro testing systems using SR vesicles found that diamide insecticides could activate dose-dependently RyR, with EC50 values of 0.14 µM (Chlorantraniliprole), 0.21 µM (Flubendiamide), and 0.57 µM (Cyantraniliprole), respectively. However, dantrolene inhibited RyR-mediated calcium release with an IC50 value of 353.9 µM, suggesting that dantrolene can weakly antagonize RyR. Moreover, cyclopiazonic acid significantly reduced the enzyme activity and calcium uptake capacity of SERCA. On the contrary, CDN1163 markedly activated the enzyme activity and improved the calcium transport capacity of SERCA. CONCLUSIONS: SR vesicles can be used to study the function of unknown proteins on the SR membranes, as well as for high-throughput screening of highly active compounds targeting RyR or SERCA. © 2024 Society of Chemical Industry.

3.
J Agric Food Chem ; 72(5): 2492-2500, 2024 Feb 07.
Artigo em Inglês | MEDLINE | ID: mdl-38271672

RESUMO

Structural diversity derivatization from natural products is an important and effective method of discovering novel green pesticides. Cinnamic acids are abundant in plants, and their unparalleled structures endow them with various excellent biological activities. A series of novel cinnamic oxime esters were designed and synthesized to develop high antifungal agrochemicals. The antifungal activity, structure-activity relationship, and action mechanism were systematically studied. Compounds 7i, 7u, 7v, and 7x exhibited satisfactory activity against Gaeumannomyces graminis var. tritici, with inhibition rates of ≥90% at 50 µg/mL. Compounds 7z and 7n demonstrated excellent activities against Valsa mali and Botrytis cinerea, with median effective concentration (EC50) values of 0.71 and 1.41 µg/mL, respectively. Compound 7z exhibited 100% protective and curative activities against apple Valsa canker at 200 µg/mL. The control effects of 7n against gray mold on tomato fruits and leaves were all >96%, exhibiting superior or similar effects to those of the commercial fungicide boscalid. Furthermore, the quantitative structure-activity relationship was established to guide the further design of higher-activity compounds. The preliminary results on the action mechanism revealed that 7n treatment could disrupt the function of the nucleus and mitochondria, leading to reactive oxygen species accumulation and cell membrane damage. Its primary biochemical mechanism may be inhibiting fungal ergosterol biosynthesis. The novel structure, simple synthesis, and excellent activity of cinnamic oxime esters render them promising potential fungicides.


Assuntos
Ascomicetos , Cinamatos , Fungicidas Industriais , Fungicidas Industriais/química , Antifúngicos/farmacologia , Relação Estrutura-Atividade , Relação Quantitativa Estrutura-Atividade , Oximas/farmacologia , Botrytis
4.
Pestic Biochem Physiol ; 198: 105728, 2024 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-38225082

RESUMO

BACKGROUND: Omphalia lapidescens is a saprophytic and parasitic fungus belonging to the Polypora genus of Tricholomataceae. It has repellent, insecticidal, anti-inflammatory and immunomodulatory effects. RESULT: This study found that the extract of O. lapidescens had significant anti-TMV activity, and the main active component was homopolysaccharide LW-1 by Bioassay-guided fractionation. LW-1 is a glucan with ß-(1,3) glucoside bond as the main chain and ß-(1,6) glucoside bond as the branch chain, with molecular weight in the range of 172,916-338,827 Da. The protective and inactive efficacies of LW-1(100 mg/L) against TMV were 78.10% and 48.20%, but had no direct effect on the morphology of TMV particles. The results of mechanism of action showed that LW-1 induced the increase of the activity of defense enzymes such as POD, SOD and PAL in Nicotiana glutinosa. The overexpression of resistance genes such as NPR1, PR1 and PR5, and the increase of SA content. Further transcriptome sequencing showed that LW-1 activated MAPK signaling pathway, plant-pathogen interaction pathway and glucosinolide metabolic pathway in Arabidopsis thaliana. Besides, LW-1 induced crops resistance against plant pathogenic fungi. CONCLUSION: Taken together, the anti-TMV mechanism of LW-1 was to activate MAPK signaling pathway, inducing overexpression of resistance genes, activating plant immune system, and improving the synthesis and accumulation of plant defencins such as glucosinolide. LW-1-induced plant disease resistance has the advantages of broad spectrum and long duration, which has the potential to be developed as a new antiviral agent or plant immune resistance inducer.


Assuntos
Arabidopsis , Vírus do Mosaico do Tabaco , Resistência à Doença/genética , Transdução de Sinais , Tabaco , Glucosídeos , Doenças das Plantas/prevenção & controle , Doenças das Plantas/genética
5.
Pest Manag Sci ; 2023 Dec 12.
Artigo em Inglês | MEDLINE | ID: mdl-38087429

RESUMO

BACKGROUND: Sclerotinia stem rot caused by Sclerotinia sclerotiorum seriously endangers oilseed rape production worldwide, and the occurrence of fungicide-resistant mutants of S. sclerotiorum leads to control decline. Thus, it is critical to explore new green substitutes with different action mechanisms and high antifungal activity. Herein, the activity and the action mechanism of natamycin against S. sclerotiorum were evaluated. RESULTS: Natamycin showed potent inhibition on the mycelial growth of S. sclerotiorum, and half-maximal effective concentration (EC50 ) values against 103 S. sclerotiorum strains ranged from 0.53 to 4.04 µg/mL (mean 1.44 µg/mL). Natamycin also exhibited high efficacy against both carbendazim- and dimethachlone-resistant strains of S. sclerotiorum on detached oilseed rape leaves. No cross-resistance was detected between natamycin and carbendazim. Natamycin markedly disrupted hyphal form, sclerotia formation, integrity of the cell membrane, and reduced the content of oxalic acid and ergosterol, whereas it increased the reactive oxygen species (ROS) and malondialdehyde content. Interestingly, exogenous addition of ergosterol could reduce the inhibition of natamycin against S. sclerotiorum. Importantly, natamycin significantly inhibited expression of the Cyp51 gene, which is contrary to results for the triazole fungicide flusilazole, indicating a different action mechanism from triazole fungicides. CONCLUSION: Natamycin is a promising effective candidate for the resistance management of S. sclerotiorum. © 2023 Society of Chemical Industry.

6.
J Agric Food Chem ; 71(46): 17713-17722, 2023 Nov 22.
Artigo em Inglês | MEDLINE | ID: mdl-37943656

RESUMO

In this investigation, the antifungal activity, its influence on the quality of apples, and the molecular mechanism of natamycin against Colletotrichum fructicola were systematically explored. Our findings indicated that natamycin showed significant inhibition against C. fructicola. Moreover, it efficaciously maintained the apple quality by modulating the physicochemical index. Research on the antifungal mechanism showed that natamycin altered the mycelial microstructure, disrupted the plasma membrane integrality, and decreased the ergosterol content of C. fructicola. Interestingly, the exogenous addition of ergosterol weakened the antifungal activity of natamycin. Importantly, natamycin markedly inhibited the expression of Cyp51A and Cyp51B genes in C. fructicola, which was contrary to the results obtained after treatment with triazole fungicide flusilazole. All these results exhibited sufficient proof that natamycin had enormous potential to be conducive as a promising biopreservative against C. fructicola on apples, and these findings will advance our knowledge on the mechanism of natamycin against pathogenic fungi.


Assuntos
Colletotrichum , Malus , Antifúngicos/farmacologia , Antifúngicos/metabolismo , Natamicina/farmacologia , Natamicina/metabolismo , Colletotrichum/metabolismo , Malus/metabolismo , Ergosterol
7.
Front Plant Sci ; 14: 1156276, 2023.
Artigo em Inglês | MEDLINE | ID: mdl-37828921

RESUMO

Drought stress (DS) is one of the main abiotic negative factors for plants. Phthalanilic acid (PPA), as a plant growth regulator, can promote the growth and development of crops. In order to evaluate the ideal application concentration and frequency of PPA-induced drought resistance in pepper (Capsicum annuum) seedlings, the concentration of PPA was 133.3 mg·L-1; 200.0 mg·L-1; 266.7 mg·L-1, and some key indicators were investigated, including leaf wilting index (LWI), relative water content (RWC), and malondialdehyde (MDA). We found that the LWI and RWC in the PPA-applied pepper leaves under light drought stress (LDS) and moderate drought stress (MDS) were all elevated, while MDA contents were decreased. To better understand how PPA makes pepper drought resistant, we examined the photosynthetic characteristics, growth parameters, antioxidant activities, and osmotic substances in pepper seedlings treated twice with PPA at a concentration of 133.3 mg·L-1 under LDS, MDS, and severe drought stress (SDS). Results showed that PPA increased the chlorophyll, plant height, stem diameter, root-shoot ratio, and seedling index of pepper leaves under LDS, MDS, and SDS. The net photosynthetic rate (Pn), stomatal conductance (Gs), intercellular CO2 concentration (Ci), transpiration rates (Tr), and water-use efficiency (WUE) in the PPA-treated pepper leaves under LDS and MDS were improved, while their stomatal limitation (Ls) were reduced. PPA also boosted the activities of enzymatic antioxidants (superoxide dismutase, catalase, and peroxidase), as well as enhanced the accumulation of osmotic substances such as soluble sugar, soluble protein, and free proline in pepper leaves under LDS, MDS, and SDS. Thus, PPA can alleviate the growth inhibition and damage to pepper seedlings caused by DS, and the PPA-mediated efficacy may be associated with the improvement in PPA-mediated antioxidant activities, Pn, and accumulation of osmotic substances.

8.
Pestic Biochem Physiol ; 195: 105571, 2023 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-37666600

RESUMO

The practical application of essential oils (EOs) as an alternative for synthetic pesticides in agricultural production is severely limited because of their instability, high volatility, and water insolubility. Nanoencapsulation of EOs is an important strategy to overcome these limitations. In view of this, this study aimed to develop chitosan-thymol nanoparticle (NCS-Thy) with pH-responsive which can be used as an intelligent botanical fungicide to control Botrytis cinerea. The NCS-Thy nanoparticle was prepared by ionic crosslinking method with the loading capacity and encapsulation efficiency of 29.87% and 41.92%, respectively. The synthesized NCS-Thy nanoparticle was further characterized by Fourier transform infrared spectroscopy analysis, transmission electron microscopy observation, and dynamic lights scattering. The results of release kinetics and antifungal activity of NCS-Thy under different pH conditions were determined. The results showed that the NCS-Thy nanoparticle had excellent pH-responsiveness and can release more thymol under acidic conditions formed by B. cinerea, thereby achieving higher antifungal effects. Therefore, compared with unencapsulated thymol, the NCS-Thy nanoparticle had higher antifungal activity against B. cinerea in vitro. In addition, both the protective and curative efficacies of detached leaf test and pot experiment were significantly higher than those of unencapsulated thymol. Among them, the protective efficacy of NCS-Thy in the pot experiment was 78.73%, which was significantly higher than that of unencapsulated thymol with 61.13%. Therefore, the pH-responsive chitosan-thymol nano-preparation had a promising prospect of application in practical management of gray mold as an intelligent botanical fungicide.


Assuntos
Quitosana , Fungicidas Industriais , Nanopartículas , Timol , Fungicidas Industriais/farmacologia , Antifúngicos/farmacologia , Quitosana/farmacologia , Concentração de Íons de Hidrogênio
9.
Pestic Biochem Physiol ; 194: 105512, 2023 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-37532363

RESUMO

The main component of orange peel essential oil is limonene. Limonene is a natural active monoterpene with multiple functions, such as antibacterial, antiseptic and antitumor activity, and has important development value in agriculture. This study found that limonene exhibited excellent anti-tobacco mosaic virus (TMV) bioactivity, with results showing that its protection activity, inactivation activity, and curative activity at 800 µg/mL were 84.93%, 59.28%, and 58.89%, respectively-significantly higher than those of chito-oligosaccharides. A direct effect of limonene on TMV particles was not observed, but limonene triggered the hypersensitive response (HR) in tobacco. Further determination of the induction activity of limonene against TMV demonstrated that it displayed good induction activity at 800 µg/mL, with a value of 60.59%. The results of physiological and biochemical experiments showed that at different treatment days, 800 µg/mL limonene induced the enhancement of defense enzymes activity in tobacco, including of SOD, CAT, POD, and PAL, which respectively increased by 3.2, 4.67, 4.12, and 2.33 times compared with the control (POD and SOD activities reached highest on the seventh day, and PAL and CAT activities reached highest on the fifth day). Limonene also enhanced the relative expression levels of pathogenesis related (PR) genes, including NPR1, PR1, and PR5, which were upregulated 3.84-fold, 1.86-fold and 1.71-fold, respectively. Limonene induced the accumulation of salicylic acid (SA), and increased the relative expression levels of genes related to SA biosynthesis (PAL) and reactive oxygen species (ROS) burst (RBOHB), which respectively increased by 2.76 times and 4.23 times higher than the control. Systemic acquired resistance (SAR) is an important plant immune defense against pathogen infection. The observed accumulation of SA, the enhancement of defense enzymes activity and the high-level expression of defense-related genes suggested that limonene may induce resistance to TMV in tobacco by activating SAR mediated by the SA signaling pathway. Furthermore, the experimental results demonstrated that the expression level of the chlorophyll biosynthesis gene POR1 was increased 1.72-fold compared to the control in tobacco treated with 800 µg/mL limonene, indicating that limonene treatment may increase chlorophyll content in tobacco. The results of pot experiment showed that 800 µg/mL limonene induced plant resistance against Sclerotinia sclerotiorum (33.33%), Phytophthora capsici (54.55%), Botrytis cinerea (50.00%). The bioassay results indicated that limonene provided broad-spectrum and long-lasting resistance to pathogen infection. Therefore, limonene has good development and utilization value, and is expected to be developed into a new botanical-derived anti-virus agent and plant immunity activator in addition to insecticides and fungicides.


Assuntos
Vírus do Mosaico do Tabaco , Limoneno/farmacologia , Ácido Salicílico/metabolismo , Clorofila/metabolismo , Superóxido Dismutase/metabolismo , Doenças das Plantas/prevenção & controle , Proteínas de Plantas/genética
10.
Angew Chem Int Ed Engl ; 62(41): e202308836, 2023 Oct 09.
Artigo em Inglês | MEDLINE | ID: mdl-37643998

RESUMO

The direct catalytic asymmetric hydrogenation of pyridines for the synthesis of piperidines remains a challenge. Herein, we report a one-pot asymmetric hydrogenation of pyridines with subsequent N-alkylation using a traceless Brønsted acid activation strategy. Catalyzed by an iridium-BINAP complex, the substrates undergo ketone reduction, cyclization and pyridine hydrogenation in sequence to form indolizidines and quinolizidines. The absolute configuration of the stereocenter of the alcohol is retained and influences the formation of the second stereocenter. Experimental and theoretical mechanistic studies reveal that the chloride anion and certain noncovalent interactions govern the stereoselectivity of the cascade reaction throughout the catalytic process.

11.
Food Chem X ; 18: 100662, 2023 Jun 30.
Artigo em Inglês | MEDLINE | ID: mdl-37025418

RESUMO

This study aimed to investigate the application potential of Portulaca oleracea extract (POE) in active packaging for the preservation of chilled meat. First, the antioxidant capacity and active ingredients of POE were systematically studied. The results demonstrated that POE has excellent antioxidant capacity and contains abundant antioxidant compounds. Subsequently, antioxidant-active packaging films based on chitosan and starch containing different concentrations of POE (CS/POE films) were successfully developed. The main physicochemical and mechanical properties of the CS/POE films were characterized and evaluated. The CS/POE films exhibited remarkable antioxidant activity and can significantly reduce lipid oxidation in meat. Compared with polyethylene film, the CS/POE films-treated meats had better preservation effects and longer shelf-life. These findings suggested that CS/POE film has the potential to become a good alternative to conventional plastics in food packaging. In conclusion, Portulaca oleracea extract is an excellent natural antioxidant with great potential in active packaging for chilled meat preservation.

12.
Pestic Biochem Physiol ; 192: 105392, 2023 May.
Artigo em Inglês | MEDLINE | ID: mdl-37105630

RESUMO

In the United States, allyl isothiocyanate (AITC) has been registered as an insecticide, bactericide, and nematicide. And it has been confirmed that AITC has significant insecticidal activities against four stored product pests including Sitophilus zeamais Mostchulky (Coleoptera: Curculionidae). This study aimed to verify the mechanism of action of AITC on cytochrome c oxidase core subunits II in S. zeamais. Enzyme - catalyzed reactions and Fourier transform infrared spectrometer (FTIR) analysis revealed that the expressed COX II proteins could competitively bind and inhibit the activity of COX II. Furthermore, molecular docking results showed that a sulfur atom of AITC could form a 2.9 Å hydrogen bond with Ile-30, having a binding energy of -2.46 kcal/mol.


Assuntos
Inseticidas , Gorgulhos , Animais , Gorgulhos/genética , Complexo IV da Cadeia de Transporte de Elétrons/genética , Complexo IV da Cadeia de Transporte de Elétrons/metabolismo , Simulação de Acoplamento Molecular , Inseticidas/farmacologia , Inseticidas/metabolismo , Clonagem Molecular
13.
Org Lett ; 25(17): 2975-2980, 2023 May 05.
Artigo em Inglês | MEDLINE | ID: mdl-37079757

RESUMO

We report the first Suzuki-Miyaura cross-coupling of 2-pyridyl ammonium salts by highly selective N-C activation catalyzed by air- and moisture-stable Pd(II)-NHC (NHC = N-heterocyclic carbene) precatalysts. The use of well-defined and highly reactive [Pd(IPr)(3-CF3-An)Cl2] (An = aniline) or [Pd(IPr)(cin)Cl] (cin = cinnamyl) Pd(II)-NHC catalysts permits an exceptionally broad scope of the cross-coupling to furnish valuable biaryl and heterobiarylpyridines that are ubiquitous in medicinal chemistry and agrochemistry research. The overall process leverages the Chichibabin C-H amination of pyridines with N-C activation to enable an attractive strategy to the 2-pyridyl problem. The utility of the method to the discovery of potent agrochemicals is presented. Considering the importance of 2-pyridines and the versatility of N-C activation methods, we envision that this new C-H/N-C activation strategy will find broad application.

14.
J Agric Food Chem ; 71(14): 5507-5515, 2023 Apr 12.
Artigo em Inglês | MEDLINE | ID: mdl-36988236

RESUMO

To overcome the high volatility, low aqueous solubility, and few definite action sites of monoterpenoid pesticides and improve their properties and effectiveness in the control of crop pathogenic fungi, herein, a series of natural turpentine-based amide derivatives exhibiting satisfactory antifungal activity were designed and synthesized. A systematic study was conducted on antifungal activity and the physiological and biochemical response of compounds 5o (EC50 = 1.139 µg/mL) and 5j (EC50 = 1.762 µg/mL) against Rhizoctonia solani. The effect of the target compound on the potential target-site succinate dehydrogenase was evaluated. The soluble concentrates of compounds 5o and 5j possessing good performance and control effects were prepared for practical application. To conduct a comprehensive analysis of the relationship between structural descriptors and activity, four representative title compounds were selected for theoretical calculation: 5o, 5j, 5k, and 5j. The binding mode of compound 5o and boscalid with succinate dehydrogenase was analyzed via molecular docking. This study provides a reference for the development of monoterpene pesticides with high efficiency, elucidated target sites, and the appropriate formula.


Assuntos
Antifúngicos , Praguicidas , Amidas , Antifúngicos/farmacologia , Simulação de Acoplamento Molecular , Relação Estrutura-Atividade , Succinato Desidrogenase/metabolismo , Terebintina , Terpenos/química , Plantas/química
15.
Plant Dis ; 107(7): 2144-2152, 2023 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-36917091

RESUMO

The essential oil of Cinnamomum camphora is the most widely consumed and used spice in the world today. It has therapeutic effects in medicine and has been shown to have good antibacterial and bacteriostatic effects in agriculture. This study found that C. camphora oil significantly induced plant disease resistance activity. Linalool, its main active component, significantly induced plant disease resistance activity (67.49% at a concentration of 800 µg/ml) over the same concentration of the chitosan oligosaccharide positive control but had no direct effect on tobacco mosaic virus (TMV). In this study of its antiviral mechanism, linalool induced hypersensitive reaction (HR); the overexpression of related defense enzymes SOD, CAT, POD, and PAL; and the accumulation of H2O2 and SA content in N. glutinosa. Besides, linalool induced crops resistance against Colletotrichum lagenarium, Botrytis cinerea, Sclerotinia sclerotiorum, and Phytophthora capsica. Taken together, the anti-TMV mechanism of linalool involved the induction of plant disease resistance through activation of a plant immune response mediated by salicylic acid. Linalool-induced plant disease resistance activity has a long duration, broad spectrum, and rich resources; linalool thus has the potential to be developed as a new plant-derived antiviral agent and plant immune activator.


Assuntos
Vírus do Mosaico do Tabaco , Vírus do Mosaico do Tabaco/fisiologia , Resistência à Doença/genética , Peróxido de Hidrogênio , Plantas
16.
J Agric Food Chem ; 2023 Feb 09.
Artigo em Inglês | MEDLINE | ID: mdl-36757172

RESUMO

Sitophilus zeamais Motschulsky (Coleoptera: Curculionidae) is a destructive pest of stored grains around the world. Allyl isothiocyanate (AITC) was shown to have good bioactivity in the control of S. zeamais. In this study, the interaction of AITC on cytochrome c oxidase core subunits I (COX I) and their binding mechanism were determined using spectroscopic, isothermal titration calorimetry and molecular docking techniques. The results indicate the binding constant (Ka) of AITC and COX I was 6.742 × 103 L/mol. Analysis of spectroscopic revealed that the binding of COX I to reduced Cyt c induced conformational changes of reduced Cyt c, while AITC could competitively bind and inhibit the activity of the COX I protein. Moreover, molecular docking results suggested a sulfur atom in the AITC structure could form a hydrogen bond having a length of 3.3 Å with the Gly- 27 of COX I.

17.
J Agric Food Chem ; 2023 Feb 09.
Artigo em Inglês | MEDLINE | ID: mdl-36757129

RESUMO

To explore insecticides targeting the γ-aminobutyric acid (GABA) receptor, two series of novel isoxazoline derivatives containing sulfonic and carboxylic esters were designed and synthesized. Their insecticidal activities against Plutella xylostella, Mythimna separata, and Aedes aegypti larvae and their structure-activity relationship were investigated. The sulfonate-containing isoxazoline derivatives (10k-q) exhibited promising insecticidal activities against the three insect larvae. Compound 10o displayed excellent activities with LC50 values of 8.32, 5.23, and 0.35 µg/mL at 48 h against P. xylostella, M. separata, and A. aegypti larvae, respectively, which were better than or similar to those of avermectin. Furthermore, compound 10o exhibited a faster insecticidal effect than avermectin against M. separata. The mode of action of 10o was preliminarily verified by molecular docking, theoretical calculations, and measurement of glutamate decarboxylase and glutamic pyruvic transaminase activities. Compound 10o is a novel insecticidal candidate acting on GABA receptors, which could guide the discovery of isoxazoline insecticides.

18.
J Agric Food Chem ; 2023 Feb 07.
Artigo em Inglês | MEDLINE | ID: mdl-36748863

RESUMO

Terpene-derived quaternary ring compounds with an oxime moiety were designed and prepared to create fungicides from natural products. A preliminary assessment of their antifungal activity against seven common pathogenic fungi was conducted, and the median effective concentration (EC50) values against Rhizoctonia solani were obtained. The effects of compound 6a19 (3-bromothiophene-containing), which had an outstanding EC50 value (1.62 µg/mL), on the morphology, ultrastructure, reactive oxygen species production, mitochondrial membrane potential, nuclear morphology, and defense-related and respiration-related enzyme activities of mycelia were evaluated. The test compound was speculated to obstruct the bio-oxidative process, inhibiting mycelial growth. Compound 6a19 exhibited a satisfactory in vivo control effect on leaf sheath-infected rice plants. After treating rice plants with 50, 100, and 200 µg/mL 6a19, the protective and therapeutic efficacy values were 48.3 and 70.3%, 58.6 and 75.7%, and 69.0 and 81.1%, respectively. Moreover, a linear quantitative structure-activity relationship (R2 = 0.932, F = 61.3, and S2 = 0.020) was established using density functional theory calculations. Four chemical descriptors that were crucial to the antifungal activity were analyzed: the number of occupied electronic levels of atoms, the minimum atomic orbital electronic population, maximum net atom charge for a H atom, and minimum net atomic charge. In overall consideration of experimental results, it was speculated that the target compounds satisfactorily inhibited R. solani by interfering with biological oxidation pathways, which provided an insight into the future intensive and systematic action mechanism. This research is promising for the invention of novel fungicides from natural terpenes with multiple potential targets and satisfactory ecological compatibility.

19.
Pest Manag Sci ; 79(6): 2098-2106, 2023 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-36693803

RESUMO

BACKGROUND: Although matrine is widely used, its absorption and transport mechanisms in crops remain unexplored. In this study, three methods including foliar application, hydroponics and seed immersion were used to investigate whether matrine molecules could enter into plants through different channels, and to further resolve its transport characteristics. The systemic activity of matrine also was evaluated. RESULT: Matrine was quickly absorbed and transported downwards after the leaves of wheat or peppers were treated, and also accumulated and transmitted upwards by roots. It was not only absorbed by seeds, but also appeared continuously in young roots and leaves in both plants for nearly 20 days. There were some differences in the uptake and conduction of matrine between pepper and wheat: matrine concentrated in pepper upper leaves with less delivered downwards to roots than in wheat, and also transduction of matrine in pepper lower leaves upwards to upper leaves was less than in wheat. Matrine had systemic activity, with LC50 of 361.99 and 904.24 µg·mL-1 against Rhopalosiphum padib on wheat and Myzus persicae (Sulzer) on pepper plants at 48 h, separately. CONCLUSION: Matrine can be absorbed by the roots, seeds and leaves of plants, and transmitted bidirectionally to any organs, presenting satisfactory systemic poisoning activity against aphids. It is of great significance to develop new formulation products of matrine and promote its commercialized value. © 2023 Society of Chemical Industry.


Assuntos
Afídeos , Capsicum , Matrinas , Animais , Afídeos/fisiologia , Matrinas/metabolismo , Sementes , Triticum
20.
Plant Dis ; 107(6): 1874-1882, 2023 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-36480731

RESUMO

Cherry tomatoes (Solanum lycopersicum) are becoming increasingly popular due to their nutrition and delicious flavor. However, cherry tomatoes are highly perishable and susceptible to various pathogenic microorganisms after harvest, such as Botrytis cinerea. In the pretest experiment, we screened out three kinds of plant essential oils (EOs) (Torreya grandis oil, Eriobotrya japonica oil, and Citrus medica oil) that have strong fungicidal activity on B. cinerea from cherry tomatoes. To further evaluate the postharvest preservation application prospect of these three oils for cherry tomatoes, the oils were extracted from different parts of three plants by hydrodistillation, and their chemical constituents were analyzed by gas chromatography-mass spectrometry. The main representative components of T. grandis oil, E. japonica oil, and C. medica oil were δ-cadinene (11.76%), transnerolidol (9.70%), and 5,7-dimethoxycoumarin (23.22%), respectively. These three EOs effectively inhibited the mycelial growth of B. cinerea in vitro, with EC50 values of 81.672, 144.046, and 221.500 µl/liter, respectively. Compared with the blank control and other oil treatments, the T. grandis oil (at a concentration of 200 µl/liter) fumigation treatment was more effective at inhibiting the growth rate of the pathogen. In addition, the phenolic content and phenylalanine ammonia lyase, ß-1,3-glucanase, chitinase, and peroxidase activities of tomatoes significantly increased on the seventh day due to the T. grandis oil treatment. The present study shows that these three oils with high extraction rates have preservation potential for cherry tomatoes. Among these three EOs, T. grandis oil can be used to further develop preservative products as a fumigant.


Assuntos
Botrytis , Óleos Voláteis , Solanum lycopersicum , Frutas/química , Fumigação , Óleos Voláteis/farmacologia
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