FirePhysChem
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2021
·
IF 0
Qi Xue,Fuqiang Bi,Junlin Zhang,Jiarong Zhang,Bozhou Wang,Minjie Wu
Two novel energetic compounds, 3-nitroxymethyl-5-(4-nitro-furazan-3-yl)-1,2,4-oxadiazole ( 4 ) and 3-nitroxymethyl-5-(4-azido-furazan-3-yl)-1,2,4-oxadiazole ( 5 ), were synthesized. Both of them were fully characterized, and the structure of 4 was further confirmed by X-ray single crystal diffraction. The thermal behaviors, detonation performances and the sensitivities of 4 and 5 were also investigated by differential scanning calorimetry (DSC), EXPLO5 program and BAM standard techniques. In addition, the electrostatic potential energy surface (ESP) was studied by Multiwfn program and density functional theory at B3LPY/6-31G (d, p). Both compounds have low melt-point, good energetic performance and mechanical sensitivity, which endow them with promising properties as plasticizing ingredients in propellant formulations.
研究领域:
有机化学
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含能材料
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晶体结构
·
热分析
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DOI
CHINESE CHEMICAL LETTERS
·
2016
·
IF 1.947
Yu-Tao Zheng,Teng-Teng Zhang,Pei-Yi Wang,Zhi-Bing Wu,Lei Zhou,Yi-Qiang Ye,Xiang Zhou,Ming He,Song Yang
By introducing the pyrazole moiety into the 5-position of 1,3,4-oxadiazole, a series of novel 2-(thioether/sulfone)-5-pyrazolyl-1,3,4-oxadiazole derivatives were synthesized. Preliminary bioassays suggested that target compounds exhibited appreciable activity against pathogenic bacteria Xanthomonas oryzae pv. oryzae ( Xoo ) and five phytopathogenic fungi in vitro . Among them, the half-maximal effective concentration (EC 50 ) values of 6c , 7a , 7b and 7c against Xoo were within 16.6 μg/mL and 65.7 μg/mL, which were better than those of commercial agricultural antibacterial bismerthiazol (92.6 μg/mL) and thiodiazole copper (121.8 μg/mL). While compounds 7a , 7b , and 7c exerted comprehensive antifungal activity toward five plant fungi, which were comparable with that of hymexazol. The results demonstrated that this kind of compounds can be further studied and developed as promising antifungal and antibacterial agents.
研究领域:
农药化学
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植物病理学
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DOI
高影响因子
JOURNAL OF POLYMER RESEARCH
·
2014
·Vol. 21
·期 11
·1-8
·
IF 1.897
Ran Xiaoqi,Yi Shixiong,Liang Liefeng,Yang Xiao
The effect of oxygen on photodegradation of π-conjugated aromatic poly(1,3,4-oxadiazole)s (POD) was studied in detail. The results obtained by tensile test, UV-spectra and ATR-FTIR revealed that the oxygen was indispensable during photodegradation of POD. The occurrence of photodegradation of POD must be combination of UV exposure and oxygen simultaneously. The state of oxygen during photodegradation of POD was investigated by nitrotetrazolium blue chloride (NBT) method. The result illustrated that the oxygen was transformed into superoxide anion radical through accepting one electron during UV exposure. Results of tensile tests and UV-spectra further proved that the superoxide anion radical could combine with excited POD to form an unstable product that lead to occurrence of photodegradation. Singlet oxygen was also investigated and the result showed that POD appeared to be stable to singlet oxygen.
研究领域:
材料科学
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化学
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产品关联
DOI
高影响因子
MONATSHEFTE FUR CHEMIE
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2023
·Vol. 154
·期 2
·215-222
·
IF 1.8
Guo Lin,Yang Shu-Qing,Zhao Kai-Chun,Chen Xiao-Chao,Lu Yong,Liu Ye
The structures of 2,5-diaryl-1,3,4-oxadiazoles with good stability have attract great attention for development of new and safe therapeutic agents with functions in antimicrobial, anti-inflammatory, antitumor, and antiviral (for treatment of HIV infection), etc. In the present work, over the developed Pd-catalytic system with involvement of the 3-thiophenyl-benzimidazolyl-based mono-phosphine, the one-pot carbonylation-dehydration tandem reaction of aryl iodides with acylhydrazines for synthesis of 2,5-diaryl-1,3,4-oxadiazoles was reported for the first time with advantages of simplified manipulations, high efficiency (yields of 62–93%), as well as high safety of applied organic substrates. The relatively high reaction temperature of 140–160 ℃ was required for this tandem reaction, wherein the good stability of the involved phosphine with suitable stereo-electronic property guaranteed the fulfilment of this sequence. It was demonstrated that the first-step carbonylation of aryl iodides with acylhydrazine toward N , N′- diarylhydrazides was the rate-determine step in the overall process. Subsequently, the formed N , N' -dibenzoylhydrazides irreversible dehydrated into 2,5-diaryl-1,3,4-oxadiazoles with the presence of dehydrating agent like DCC. Graphical abstract
研究领域:
有机化学
·
药物化学
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DOI
高影响因子
JOURNAL OF ORGANIC CHEMISTRY
·
2023
·
IF 3.6
Qijie Zou,Wei Zhang,Haoyue Wang,Guangwei Yin,Yongzhi He,Fangyi Li
The CF3 group attached to N-aryl hydrazone could be activated upon treatment with a suitable base, thus serving as an excellent C1 unit for the assembly of a series of 1,3,4-oxadiazoles by reaction with hydrazides. The transformation is proposed to proceed via the intermediate formation of a gem-difluorinated azoalkene. Furthermore, this reaction features simple conditions and a broad substrate scope with respect to both trifluoromethyl N-aryl hydrazones and hydrazides.
研究领域:
有机化学
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合成化学
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
·
2024
·
IF 1.3
Huang Pengmian,Yang Ting,Liu Jiyong,Xiang Juncheng,Wu Minghui
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.
研究领域:
农药化学
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有机合成
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植物保护
✓ 已验证
DOI
高影响因子
Frontiers of Chemical Science and Engineering
·
2021
·Vol. 16
·期 7
·1090-1100
·
IF 4.204
Wen Yong-Hui,Cheng Long,Xu Tian-Ming,Liu Xing-Hai,Wu Ning-Jie
Twenty six novel pyrimidin-4-amine derivatives containing the 1,2,4-oxadiazole motif were synthesized. Their chemical structures were confirmed by 1 H nuclear magnetic resonance (NMR), 13 C NMR, and highresolution mass spectrography. The insecticidal activity results indicated that some of them possessed excellent insecticidal activity (100%) against Mythimna separate , especially for compounds 6d, 6f, 6o, 6w, 6y and 6z . These compounds exhibited no activity against the insects Aphis medicagini and Tetranychus cinnabarinus . The structure-insecticidal activity relationships are discussed. Density functional theory analysis can potentially be used to design more active compounds. These results provide useful insecticide design information for further optimization.
研究领域:
农药化学
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计算化学
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药物设计
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昆虫毒理学
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有机合成
✓ 已验证
DOI
高影响因子
JOURNAL OF POLYMER RESEARCH
·
2013
·Vol. 20
·期 7
·1-9
·
IF 2.019
Xu Jingmei,Ren Chunli,Cheng Hailong,Ma Li,Wang Zhe
Double fluoride 2,5-bis(4-fluorophenyl)-1,3,4-oxadiazole (BFO) monomer was synthesized. Copolymerization of BFO, 2,2-bis(4-hydroxypheny)propane (bisphenol A) and 3′3-disulfonate-4′4-dichloro dipheny sulfone (SDCDPS) at different molar ratio resulted in a new poly (aryl ether sulfone) containing 1, 3, 4-oxadiazole polymers (SPAESO). The structures of monomer BFO and copolymer were confirmed by FT-IR and 1 H NMR. The TEM pictures showed that the ion clusters were formed and distributed evenly in SPAESO copolymer matrix. The sulfonated polyoxadiazole membranes exhibited excellent thermal, dimensional and oxidative stability and lower methanol diffusion coefficient. The proton conductivity of SPAESO-3 was 7.5 × 10 −2 Scm −1 at 120 °C while the methanol permeability coefficient of SPAESO-3 was only 2.23 × 10 −7 cm 2 S −1 at 25 °C. According to the comprehensive performance, the sulfonated polyoxadiazole membranes may be the alternative materials as proton exchange membrane for PEMFC at medium-high temperature operation.
研究领域:
高分子化学
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燃料电池技术
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功能材料科学
✓ 已验证
DOI
高影响因子
ACS Omega
·
2023
·
IF 4.1
Nianjuan Pan,Hui Wang,Jiansong An,Chunyi Liu,Haijiang Chen,Qiang Fei,Pei Li,Wenneng Wu
In recent years, the severity of plant diseases caused by plant pathogenic fungi and viruses has been on the rise. However, there is a limited availability of pesticide chemicals in the market for effectively controlling both fungal and viral infections. To solve this problem, a series of novel pyrimidine derivatives containing a 1,3,4-oxadiazole thioether fragment were synthesized. Among them, compound 6s exhibited remarkable in vivo protection activity against tobacco mosaic virus, demonstrating the superior 50% effective concentration (EC50) value of 0.42 μM, outperforming ningnanmycin (0.60 μM). Meanwhile, compound 6s exhibited remarkable antifungal activity against Botrytis cinerea Pers. in postharvest blueberry in vitro, with an EC50 value of 0.011 μM, surpassing the inhibition rate of Pyrimethanil (0.262 μM). Additionally, compound 6s also demonstrated remarkable curative and protection activities against blueberry fruit gray mold in vivo, with control efficiencies of 54.2 and 60.4% at 200 μg/mL concentration, respectively, which were comparable to those of Pyrimethanil (49.3 and 63.9%, respectively). Scanning electron microscopy showed that the compound 6s-treated hyphae of B. cinerea Pers. in postharvest blueberry became abnormally collapsed and shriveled. Furthermore, the molecular docking simulation demonstrated that compound 6s formed hydrogen bonds with SER-17, ARG-43, and SER-39 of succinate dehydrogenase (SDH), providing a possible explanation for the mechanism of action between the target compounds and SDH. This study represents the first report on the antiviral and antifungal activities of novel pyrimidine derivatives containing a 1,3,4-oxadiazole thioether fragment.
研究领域:
植物病理学
·
农药化学
·
分子生物学
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DOI
PubMed
高影响因子
MOLECULAR DIVERSITY
·
2025
·
IF 3.8
Li Yong,Wu Taotao,Chen Guobin,He Jian,Zhang Yong,Zhang Qin,Zhou Pengfei,Chen Wenzhang,Fan Lingling
Twenty-eight novel phthalide derivatives incorporating thiazole, 1,3,4-oxadiazole, and oxime ether moieties were designed and synthesized using a pharmacophore hybridization strategy. Bioactivity assays demonstrated that compounds 1b , 1c , 4a , 4b and 4c exhibited moderate to excellent inhibitory activity against several specific fungi. Notably, compound 1b displayed superior antifungal efficacy against F. solani , F. oxysporum , B. dothidea , and V. mali compared to the commercial fungicides hymexazol and boscalid , with EC 50 values of 15.0 μ g/mL , 10.0 μ g/mL, 6.1 μ g/mL, and 11.4 μ g/mL, respectively. Additionally, compound 1b provided superior protective efficacy against B. dothidea- infected apples compared to boscalid. Preliminary mechanistic studies revealed that compound 1b could exert its antifungal activity by compromising the integrity of the hyphal cell membrane. This study highlights the potential of phthalide derivatives bearing dihalocarbonyl and oxime moieties as effective antifungal agents for controlling plant pathogenic fungi, warranting further investigation in the future. Graphical
研究领域:
药物化学
·
抗菌剂
·
真菌生物学
·
植物病理学
·
药效团杂交
✓ 已验证
DOI
PubMed
高影响因子
PEST MANAGEMENT SCIENCE
·
2016
·Vol. 73
·期 5
·917-924
·
IF 2.811
Qi Liu,Rui Zhu,Shang Gao,Shi-Han Ma,Hai-Jun Tang,Jian-Jun Yang,Ya-Mei Diao,Hong-Lei Wang,Hong-Jun Zhu
BACKGROUND Anthranilic diamide derivatives are among the most important classes of synthetic insecticides. Moreover, the 1,2,4-oxadiazole heterocycle, a bioisostere of amide, has been extensively used in pesticides. In order to discover novel molecules with high insecticidal activities, a series of anthranilic diamide analogues containing 1,2,4-oxadiazole rings were designed and synthesised. RESULTS A series of novel anthranilic diamide derivatives containing 1,2,4-oxadiazole were obtained, and confirmed by 1 H and 13 C nuclear magnetic resonance and high-resolution mass spectrometry. The structure of 3-bromo- N -(4-chloro-2-methyl-6-{3-[(methylsulphonyl)methyl]-1,2,4-oxadiazol-5-yl}phenyl)-1-(3-chloropyridin-2-yl)-1 H -pyrazole-5-carboxamide was further characterised by X-ray diffraction analysis. In addition, bioassays showed that most of the newly synthesised compounds displayed 100% mortality against Plutella xylostella at 100 mg L −1 , and compound 3IIl showed 90% larvicidal activities at a concentration of 0.5 mg L −1 . The LC 50 value of 3IIl was 0.20 mg L −1 , which indicated that it may be used as a potential leading compound for further structural optimisation. Furthermore, brief comparative molecular field analysis (CoMFA) models were established to study the structure–activity relationships (SARs) of the title compounds. CONCLUSION Compound 3IIl may be used as a potential leading compound for further structural optimisation, and SARs and CoMFA models could provide reliable clues for further structural optimisation. © 2016 Society of Chemical Industry
研究领域:
农药化学
·
有机合成
·
生物活性研究
✓ 已验证
DOI
高影响因子
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
·
2022
·Vol. 23
·期 3
·1596
·
IF 6.208
Dan Liu,Ling Luo,Zhengxing Wang,Xiaoyun Ma,Xiuhai Gan
Plant diseases that are caused by fungi and nematodes have become increasingly serious in recent years. However, there are few pesticide chemicals that can be used for the joint control of fungi and nematodes on the market. To solve this problem, a series of novel 1,2,4-oxadiazole derivatives containing amide fragments were designed and synthesized. Additionally, the bioassays revealed that the compoundF15demonstrated excellent antifungal activity againstSclerotinia sclerotiorum(S. sclerotiorum) in vitro, and the EC50value of that was 2.9 μg/mL, which is comparable with commonly used fungicides thifluzamide and fluopyram. Meanwhile,F15demonstrated excellent curative and protective activity againstS. sclerotiorum-infected cole in vivo. The scanning electron microscopy results showed that the hyphae ofS. sclerotiorumtreated withF15became abnormally collapsed and shriveled, thereby inhibiting the growth of the hyphae. Furthermore,F15exhibited favorable inhibition against the succinate dehydrogenase (SDH) of theS. sclerotiorum(IC50= 12.5 μg/mL), and the combination mode and binding ability between compoundF15and SDH were confirmed by molecular docking. In addition, compoundF11showed excellent nematicidal activity againstMeloidogyne incognitaat 200 μg/mL, the corrected mortality rate was 93.2%, which is higher than that of tioxazafen.Keywords:1,2,4-oxadiazole;antifungal activity;nematicidal activity;succinate dehydrogenase
研究领域:
农业化学
·
植物病理学
·
农药科学
✓ 已验证
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）