Design, Synthesis, and Bioactivity of Eighteen Novel 2H-1,4-Benzoxazin-3(4H)-one Containing a Propanolamine Moiety.

To develop a novel skeleton for broad-spectrum pesticides with high-efficiency against tea tree diseases, a series of aniline 2H-1,4-benzoxazin-3(4H)-one derivatives containing a propanolamine structure was synthesized and confirmed by 1 H-NMR, 13 C-NMR, 19 F-NMR, HRMS, and single-crystal diffraction analysis. Bioactivities were evaluated against tobacco mosaic virus (TMV, the model virus), three kinds of bacteria, and five typical plant fungi. Bioassay results showed that compound 2i (EC50 =395.05 µg/mL) had the best curative activity against TMV, 3d (EC50 =45.70 µg/mL) had the best inhibitory activity against Pseudomonas syringae pv. Actinidiae, and 3a (EC50 =13.53 µg/mL) had the best inhibitory activity against Pestalotiopsis trachicarpicola. Scanning electron microscope morphological observation of P. trachicarpicola treated with 0, 100, and 200 µg/mL 3a revealed dried, flattened and folded outer walls of the hyphae at higher concentrations, leading to inhibition of fungal growth. The broad-spectrum bioactivities (against viruses, bacteria and fungi) of this series of target compounds indicate that these 2H-1,4-benzoxazin-3(4H)-one derivatives containing a propanolamine moiety are potential skeletons for developing pesticides with wide-ranging activities against various tea tree diseases.

Antibiotic activities of propanolamine containing 1,4-benzoxazin-3-ones against phytopathogenic bacteria.

Various 1,4-benzoxazin-3-one derivatives containing propanolamine groups have been shown to exhibit good antibacterial activity against Pseudomonas syringae pv actinidiae (Psa), X. axonopodis pv citri (Xac) and Xanthomonas oryzae pv oryzae (Xoo). 1,4-benzoxazin-3-one 4n showed the best inhibitory effects against Psa, Xac and Xoo, exhibiting in vitro EC50 values of 4.95, 4.71 and 8.50 µg mL-1, respectively. These potencies were superior to the corresponding EC50 values of the commercial antibiotics bismerthiazol (BT, 89.10, and 116.90 µg mL-1) and thiodiazole copper (TC, 127.30, 82.73 and 87.50 µg mL-1). Treatment on the bacterial leaf blight of rice revealed that compound 4n displayed better curative (51%) and protective (48%) activities for reducing rice BLB than either BT (41%, 39%) or TC (43%, 41%). Scanning electron microscopy (SEM) imaging of Xoo that had been treated with 1,4-benzoxazin-3-one 4n (50-100 µg mL-1) revealed that the bacterial cells had experienced extensive cell wall damage, which is the likely cause of its antimicrobial activity and bacterial death.

Rational Optimization and Action Mechanism of Novel Imidazole (or Imidazolium)-Labeled 1,3,4-Oxadiazole Thioethers as Promising Antibacterial Agents against Plant Bacterial Diseases.

The emergence and widespread occurrence of plant bacterial diseases that cause global production constraints have become major challenges to agriculture worldwide. To promote the discovery and development of new bactericides, imidazole-labeled 1,3,4-oxadiazole thioethers were first fabricated by integrating the crucially bioactive scaffolds of the imidazole motif and 1,3,4-oxadiazole skeleton in a single molecular architecture. Subsequently, a superior antibacterial compound A6 was gradually discovered possessing excellent competence against plant pathogens Xanthomonas oryzae pv oryzae and Xanthomonas axonopodis pv citri with EC50 values of 0.734 and 1.79 µg/mL, respectively. These values were better than those of commercial agents bismerthiazol (92.6 µg/mL) and thiodiazole copper (77.0 µg/mL). Further modifying the imidazole moiety into the imidazolium scaffold led to the discovery of an array of potent antibacterial compounds providing the corresponding minimum EC50 values of 0.295 and 0.607 µg/mL against the two strains. Moreover, a plausible action mechanism for attacking pathogens was proposed based on the concentration dependence of scanning electron microscopy, transmission electron microscopy, and fluorescence microscopy images. Given the simple molecular structures, easy synthetic procedure, and highly efficient bioactivity, imidazole (or imidazolium)-labeled 1,3,4-oxadiazole thioethers can be further explored and developed as promising indicators for the development of commercial drugs.

Ultrahigh conductivity of graphene nanoribbons doped with ordered nitrogen.

Graphene is an attractive candidate for developing high conductivity materials (HCMs) owing to an extraordinary charge mobility. While graphene itself is a semi-metal with an inherently low carrier density, and methods used for increasing carrier density normally also cause a marked decrease in charge mobility. Here, we report that ordered nitrogen doping can induce a pronounced increase in carrier density but does not harm the high charge mobility of graphene nanoribbons (GNRs), giving rise to an unprecedented ultrahigh conductivity in the system. Our first-principles calculations for orderly N-doped GNRs (referred to as C5N-GNRs) show that N-doping causes a significant shift-up of the Fermi level (ΔE F), resulting in the presence of multiple partially-filled energy bands (PFEDs) that primarily increase the carrier density of system. Notably, the PFEDs are delocalized well with integral and quantized transmissions, suggesting a negligible effect from N-doping on the charge mobility. Moreover, the PFEDs can cross the E F multiple times as the ribbon widens, causing the conductivity to increase monotonically and reach ultrahigh values (>15G 0) in sub-5 nm wide ribbons with either armchair or zigzag edges. Furthermore, a simple linear relationship between the doing concentration and the ΔE F was obtained, which provides a robust means for controlling the conductivity of C5N-GNRs. Our findings should be useful for understanding the effect of ordered atomic doping on the conductivity of graphene and may open new avenues for realizing graphene-based HCMs.

Coherent Φ-OTDR based on I/Q demodulation and homodyne detection.

We demonstrate a novel distributed acoustic sensing (DAS) system based on phase-sensitive optical time-domain reflectometry (Φ-OTDR). Both the phase and the amplitude of the Rayleigh scattering (RS) light can be demodulated in real-time. The technique is based on I/Q demodulation and homodyne detection using a 90° optical hybrid. The theoretical analysis is given, and as a proof of the concept, the dynamic strain sensing is experimentally demonstrated, with a sensing range of 12.566 km and a spatial resolution of 10 m.