To discover new bisamide compounds with insecticidal and fungicidal activities, 19 novel cyproflanilide derivatives containing 1,2,4-oxadiazole group were designed and synthesized according to the principle of biologically active factor splicing. Preliminary biological assay data indicated that the majority of target compounds demonstrated significant insecticidal activity against Lepidopteran pests. Meanwhile, compounds 5p and 5q showed 97.22 and 100% lethality against Tetranychus cinnabarinus at 400 mg L-1, which were better than cyproflanilide (41.11% at 400 mg L-1). In addition, it is exciting that we have achieved our initial goals as some of the target compounds exhibited both insecticidal and fungicidal activities. For instance, compounds 5b and 5c showed 59.26 and 74.07% fungicidal activities against Cucumber downy mildew at 400 mg L-1, as well as 100% insecticidal activity against Plutella xylostella and armyworm at 100 mg L-1. Compound 5h showed 100% insecticidal activity against armyworm at 10 mg L-1, and also displayed 66.67% fungicidal activity against Cucumber downy mildew at 400 mg L-1. The inhibition rate of compounds 5l and 5s against Cucumber downy mildew reached 88.89 and 96.30% at 400 mg L-1. This work showed the effectively fungicidal application of 1,2,4-oxadiazole group in bisamide compounds and provides insights for optimal structural design.
Pyrazole derivatives with polynitro groups were extensively researched in energetic material field as they show high energy density and excellent detonation properties, but the specific synthesis process still encounters challenges. In this paper, we firstly combined trinitromethyl, dinitroethyl, oxadiazolyl moieties with pyrazole, successfully designed and synthesized three novel poly-nitro pyrazole energetic compounds by nitration. Their structural features were investigated using single-crystal X-ray diffraction, nuclear magnetic resonance, infrared spectroscopy. 3-(3,5-Dinitro-1 H -pyrazol-4-yl)-1,2,4-oxadiazol-5(4 H )-one ( 12 ) possessed a superior thermal stability (235.1 °C) due to the presence of strong conjugated interaction in this structure. Among all, 3-nitro-1-(trinitromethyl)-1 H -pyrazole-5-carboxylic acid ( 8 ) exhibited a good thermal stability (163.7 °C), a high density of 1.829 g cm −3 at 298 K in combination with excellent detonation properties ( D : 8747 m s −1 ; P : 33.613 GPa). The results indicate that three compounds have promise to act as novel energetic materials and the synthesis provides a direction for polynitro compounds and oxadiazol based energetic compounds.
Four π-extended viologen derivatives (Spr-PO/Sbu-PO/OHpr-PO/ OHet-PO) were synthesized by introducing oxadiazole group and side chain modification. Compared with viologen with bipyridines as the chromophore, these POs possessed extended conjugation lengths and optimized photoelectron conversion efficiency. The CMC gel electrochromic devices based on them could realize the color transformation from colorless to yellow-green under the working voltage of 1.1 V. Furthermore, due to different side chain groups, the diffusion rates of POs in the gel changed significantly. Compounds based on hydroxyl side chain groups showed higher response rates (<10 s) in the CMC gel system, while sulfonate side chain modified POs showed slower response characteristics (>10 s). All POs showed excellent stability, the optical contrasts were almost unchanged after continuous working for 100 cycles. This study provided an important method for obtaining efficient and stable electrochromic devices.
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