Novel <i>trans</i>-Ferulic Acid Derivatives Containing a Chalcone Moiety as Potential Activator for Plant Resistance Induction

A series of novel <i>trans</i>-ferulic acid derivatives containing a chalcone moiety were designed and synthesized to induce plant resistance. Antiviral activities of the compounds were evaluated. Bioassay results demonstrated that compounds <b>F3</b>, <b>F6</b>, <b>F17</b>, and <b>F27</b> showed remarkable curative, protective, and inactivating activities against tobacco mosaic virus (TMV). With a 50% effective concentration (EC₅₀) value of 98.78 μg mL^–1, compound <b>F27</b> exhibited the best protective activity compared with <i>trans</i>-ferulic acid (328.6 μg mL^–1), dufulin (385.6 μg mL^–1), and ningnanmycin (241.3 μg mL^–1). This protective ability was associated with potentiation of defense-related enzyme activity and activation of photosynthesis of tobacco at an early stage. This notion was confirmed by up-regulated expression of stress responses and photosynthesis regulating proteins. This work revealed that <b>F27</b> can induce resistance and enhance plant tolerance to TMV infection. Hence, <b>F27</b> can be considered as a novel activator for inducing plant resistance

Characterization of Sulfoxaflor and Its Metabolites on Survival, Growth, Reproduction, Biochemical Markers, and Transcription of Genes of Daphnia magna

Sulfoxaflor is a promising neonicotinoid. However, the negative implications of sulfoxaflor on nontarget aquatic organisms have been rarely studied. In this study, the risks of sulfoxaflor and its main metabolites X11719474 and X11519540 on Daphnia magna were characterized, including acute toxicity, reproduction, swimming behavior, biochemical markers, and gene transcription. Acute toxicity measurements indicated that X11719474 and X11519540 have high toxicity than the parent compound sulfoxaflor. Chronic exposure reduced reproduction and delayed the birth of the firstborn D. magna. Swimming behavior monitoring showed that exposure to three compounds stimulated swimming behavior. The induction of catalase, superoxide dismutase, and acetylcholinesterase activities was observed with oxidative stress, whereas malondialdehyde content was remarkably increased with exposure to sulfoxaflor, X11719474, and X11519540. Moreover, transcriptomics profiles showed that sulfoxaflor, X11719474, and X11519540 induced KEGG pathways related to cellular processes, organismal systems, and metabolisms. The findings present valuable insights into the prospective hazards of these pesticides and emphasize the critical importance of conducting a systematic evaluation of combining antecedents and their metabolites

Synthesis and Antiviral Activity of Novel <i>α</i>-Aminophosphorus Containing Benzofuran Moiety

<div><p>GRAPHICAL ABSTRACT</p><p></p></div

Design, Synthesis, and Evaluation of New Sulfone Derivatives Containing a 1,3,4-Oxadiazole Moiety as Active Antibacterial Agents

This study aimed to synthesize some new sulfone derivatives containing a 1,3,4-oxadiazole moiety and investigate their in vitro antibacterial activities against <i>Xanthomonas oryzae</i> pv. <i>oryzae</i> (<i>Xoo</i>) and <i>Xanthomonas axonopodis</i> pv. <i>citri</i> (<i>Xac</i>), the pathogens of rice bacterial leaf blight and citrus canker, respectively, by performing turbidimeter tests. Antibacterial bioassay results showed that compound <b>6d</b> revealed excellent bioactivities against <i>Xoo</i> and <i>Xac</i>, with the 50% effective concentration (EC₅₀) values of 0.17 and 1.98 μg/mL, respectively, compared with thiodiazole copper (121.82 and 77.04 μg/mL, respectively) and bismerthiazol (92.61 and 58.21 μg/mL, respectively). Meanwhile, greenhouse-condition trials indicated that, compared with thiodiazole copper and bismerthiazol, compound <b>6d</b> more effectively reduced rice bacterial leaf blight

Design, Synthesis, and Insecticidal Activity of Novel Isoxazoline Compounds That Contain <i>Meta</i>-diamides against Fall Armyworm (Spodoptera frugiperda)

Fall armyworm (Spodoptera frugiperda) is a major migratory pest around the entire world that causes severe damage to agriculture. We designed and synthesized a series of novel isoxazoline derivatives based on the previously discovered active compound H13 to find new and effective candidates against S. frugiperda. Most of them showed excellent insecticidal activity. In addition, a three-dimensional quantitative structure–activity relationship model was established, and compound F32 was designed and synthesized based on the results. The bioassay result showed that compound F32 exhibited excellent activity against S. frugiperda (LC50 = 3.46 mg/L), which was substantially better than that of the positive control fipronil (LC50 = 78.8 mg/L). Furthermore, an insect γ-aminobutyric acid (GABA) enzyme-linked immunosorbent assay indicated that F32 can upregulate the content of GABA in insects in a manner similar to that of fipronil. Molecular docking showed that the hydrophobic effect and hydrogen-bond interactions are vital factors between the binding of F32 and receptors. All of these results suggest that compound F32 could be employed as a novel isoxazoline lead compound to control S. frugiperda

Asymmetric Synthesis and Bioselective Activities of α‑Amino-phosphonates Based on the Dufulin Motif

The asymmetric synthesis of enantiomerically pure α-aminophosphonates with high and bioselective activities is a challenge. Here, we report that both enantiomers of α-aminophosphonates bearing the <i>N</i>-benzothiazole moiety can be prepared in high yields (up to 99%) and excellent enantioselectivities (up to 99% ee) by using chiral thiourea organocatalysts. Evaluation of the antiviral activities of our reaction products against cucumber mosaic virus (CMV) led to promising hits with high and selective biological activities, wherein (<i>R</i>)-enantiomers exhibit higher biological activities than the corresponding (<i>S</i>)-enantiomers. Especially, compound (<i>R</i>)-<b>3b</b> with excellent anti-CMV activity (curative activity, 72.3%; protection activity, 56.9%; and inactivation activity, 96.9%) at 500 μg/mL emerged as a potential inhibitor of the plant virus. The difference in the selective bioactivity could be affected by the combination mode of the three-dimensional space between the enantiomers of α-aminophosphonate and cucumber mosaic virus coat protein (CMV-CP) via florescence spectroscopy and molecular docking

Residue dynamics and risk assessment of dimethoate in sweet potato, purple flowering stalk, Chinese kale, celery, and soil

<p>Residue dynamics and risk assessment of the insecticide dimethoate applied to sweet potato, purple flowering stalk, Chinese kale, celery were investigated under the climatic conditions of China. The dissipation experiments indicated that the half-lives of dimethoate in purple flowering stalk, Chinese kale, celery, and soil were 5.9–6.5, 3.8–5.1, 3.5–5.4, 3.4–3.6 d, respectively. The terminal residues of dimethoate and omethoate in the vegetables and soil ranged from 0.008 to 1.73 mg kg⁻¹ at preharvest intervals of 3, 5, and 7 d. The results showed risk quotient (RQ) of <1 for sweet potato, Chinese kale, and celery, and of >1 for purple flowering stalk when under the age of 18, indicating that spraying dimethoate on sweet potato, Chinese kale, and celery at the recommended dosage is safe for human consumption, whereas spraying it on purple flowering stalk is associated with some risks to human health.</p

Design, Synthesis, Antiviral Bioactivity, and Defense Mechanisms of Novel Dithioacetal Derivatives Bearing a Strobilurin Moiety

A series of dithioacetal derivatives bearing a strobilurin moiety were designed and synthesized on the basis of our previous work. The antiviral activities of these compounds against Potato virus Y (PVY), Cucumber mosaic virus (CMV), and Tobacco mosaic virus (TMV) were systematically evaluated. Bioassay results indicated that <b>C14</b> elicited excellent curative and protective activities against PVY, CMV, and TMV. The former had 50% effective concentrations (EC₅₀) of 125.3, 108.9, and 181.7 μg/mL, respectively, and the latter had 148.4, 113.2, and 214.6 μg/mL, respectively, which were significantly superior to those of lead compound <b>6f</b> (297.6, 259.6, and 582.4 μg/mL and 281.5, 244.3, and 546.3 μg/mL, respectively), Ningnanmycin (440.5, 549.1, and 373.8 μg/mL and 425.3, 513.3, and 242.7 μg/mL, respectively), Chitosan oligosaccharide (553.4, 582.8, and 513.8 μg/mL and 547.3, 570.6, and 507.9 μg/mL, respectively), and Ribavirin (677.4, 690.3, and 686.5 μg/mL and 652.7, 665.4, and 653.4 μg/mL, respectively). Moreover, defensive enzyme activities and RT-qPCR analysis demonstrated that the antiviral activity was associated with the changes of SOD, CAT, and POD activities in tobacco, which was proved by the related proteins of abscisic acid signaling pathway. This work provided a basis for further design, structural modification, and development of dithioacetal derivatives as new antiviral agents

Synthesis and antiviral activity of novel thioether derivatives containing 1,3,4-oxadiazole/thiadiazole and emodin moieties

<p>A series of novel thioether derivatives containing 1,3,4-oxadiazole/thiadiazole and emodin moieties were designed and synthesized. The structures of the target compounds were confirmed by ¹H NMR, ¹³C NMR, Infrared, and elemental analysis. The results of bioactivity analysis showed that most of the target compounds exhibited moderate to good antiviral activity against tobacco mosaic virus at a concentration of 500 mg/L. Especially, among the title compounds, <b>Y2</b>, <b>Y8</b>, and <b>Y10</b> possessed appreciable curative activity in vivo, with inhibition rates of 50.51, 52.08, and 54.62%, respectively, which were similar to that of Ningnanmycin (53.40%).</p

Additional file 1: of N 6 -methyl-adenosine level in Nicotiana tabacum is associated with tobacco mosaic virus

Figure S1. Calibration curves for the quantification of A in mRNA. The amounts of A ranged from 0.1–2.5 μmol. Figure S2. Calibration curves for the quantification of C in mRNA. The amounts of C ranged from 0.5–25 μmol. Figure S3. Calibration curves for the quantification of G in RNA. The amounts of G ranged from 0.25–12.5 μmol. Figure S4. Calibration curves for the quantification of U in RNA. The amounts of U ranged from 5 to 250 μmol. Figure S5. Calibration curves for the quantification of m6A in RNA. The amounts of m6A ranged from 0.005–0.250 μmol. Figure S6. Representative UHPLC-HR-MS/MS results for the quantification of A in N. tabacum K326 with selected-ion chromatograms. Figure S7. Representative UHPLC-HR-MS/MS results for the quantification of C in N. tabacum K326 with selected-ion chromatograms. Figure S8. Representative UHPLC-HR-MS/MS results for the quantification of U in N. tabacum K326 with selected-ion chromatograms. Table S1. Primer sequences for RT-qPCR analysis. (PDF 1250 kb