基于Ugi反应的新型鱼尼丁受体杀虫剂的设计、合成及生物活性

利用Ugi 反应设计合成了一系列未见文献报道的α-苯基-α-酰胺基-酰胺类化合物, 所有化合物均通过 ¹H NMR谱、元素分析和高分辨质谱表征确定. 初步的生物活性测试结果表明, 在浓度为200 mg/L时, 化合物7h对粘虫有一定抑制活性; 在浓度为50 mg/L时, 化合物7q对苹果轮纹病菌、化合物7e对小麦赤霉菌有一定的抑菌活性.     

新型邻甲酰胺基间苯二甲酰胺类化合物的 设计合成及生物活性

以氯虫酰胺结构为基础,设计合成了一系列新型邻甲酰胺基间苯二甲酰胺类化合物,所有化合物均通过核磁共振氢谱和高分辨质谱表征确定.初步的生物活性测试结果表明,在浓度为200 mg/L时,化合物8d的杀粘虫活性可达60％;在浓度为50 mg/L时,化合物8d对苹果轮纹病菌的抑菌率为41.7％,化合物8a对小麦赤霉菌的抑菌率为4...     

新型含甲氨甲酰苯基烟酰脲类化合物的设计、合成及生物活性研究

为了寻找新的农药先导化合物,以氯虫苯甲酰胺和2-氯烟酸结构为基础,依据生物合理设计思想引入酰脲活性基团,设计合成了12个结构新颖的烟酰脲类化合物.其结构经1H NMR,13C NMR,IR及HRMS确认.初步的生测活性测试结果表明,部分化合物对粘虫(Mythimna separata)具有较好的杀虫活性,在浓度为500 mg/L时,化合物5a,5g和5h处理的粘虫死亡率为100%;此外,部分化合物具有一定的除草活性,其中100 mg/L的化合物5f对稗草(Echinochloa crusgalli)根部生长抑制率为80%.     

含七氟异丙基的氯虫酰胺类似物的设计合成及生物活性

以氯虫酰胺和氟虫酰胺结构为基础,通过活性基团拼接法,设计合成了一系列新的含七氟异丙基的氯虫酰胺类似物,所有化合物通过了核磁共振氢谱和高分辨质谱的表征,并测试了它们的杀虫和杀菌活性。     

取代噻吩双酰胺类化合物的设计、 合成及生物活性

利用中间体衍生化方法, 将噻吩环引入到双酰胺类化合物中, 合成了一系列取代噻吩双酰胺类化合物1~3; 目标化合物的结构经核磁共振波谱、 红外光谱及元素分析确认. 生物活性测试结果表明, 化合物1在600 mg/L剂量下对小菜蛾具有良好的杀虫效果, 致死率均为100%, 其中化合物1a和1e在20 mg/L剂量下对小菜蛾的致死率仍达到60%以上; 改变双酰胺结构中的吡唑环得到化合物2和3, 其杀虫活性消失, 说明该类化合物中吡唑环结构对杀虫活性具有关键作用.     

新型含酰基脲桥和硫脲桥的苯双酰胺类似物的合成及生物活性

参考氟虫酰胺和除虫脲的活性结构片段,设计合成了一系列结构新颖的含有酰基脲桥和酰基硫脲桥的化合物,通过核磁共振氢谱、高分辨质谱以及X射线单晶衍射确定了其结构.生测结果表明,酰基脲桥和酰基硫脲桥结构的引入使杀虫活性降低,但是化合物7d在10 mg/L的浓度下,仍表现出一定的杀粘虫活性.此外发现部分化合物具有一定的抑菌活性,其中化合物8f对苹果轮纹、小麦纹枯和水稻恶苗病原菌的抑制率分别为75.0%、87.5%和84.6%.     

含N-吡啶联吡唑杂环的(磺)酰胺类化合物的设计、合成及生物活性

以氯虫酰胺结构为基础, 设计合成了一系列含N-吡啶联吡唑杂环的酰胺及磺酰胺类化合物. 所有化合物的结构均通过元素分析和 ¹H NMR确证. 生物活性测试结果表明, 部分化合物对东方粘虫(4龄幼虫)和尖音库蚊(幼虫)表现出较好的杀灭活性. 化合物4a, 4k和5b在浓度为100 mg/L时对东方粘虫(4龄幼虫)的致死率均高于50%, 化合物4g 在浓度为2 mg/L时对尖音库蚊(幼虫)的致死率达100%.     

阿魏酸酰腙类化合物的合成及生物活性

将酰腙结构引入到阿魏酸衍生物中,合成了6个阿魏酸酰腙类化合物,其结构经过了IR、~1H NMR、~(13)C NMR和ESI-HRMS表征。抗病毒活性测试结果表明,在质量浓度为500mg/L时,化合物3、5和6对烟草花叶病毒(TMV)在保护、治疗和钝化活性方面的抑制率均优于对照药剂病毒唑。进一步的EC_(50)测试结果表明,化合物3、5和6钝化活性的EC_(50)值分别为91.25、54.86、58.22mg/L,明显低于病毒唑的EC_(50)值(126.05mg/L)。该研究结果表明,阿魏酸酰腙类化合物对TMV具有较好的抗病毒活性,对其进行适当的结构改进和优化,有望得到具有更高抗病毒活性的化合物。     

三嗪酮杀虫活性分子的合成及生物活性

为发展更加高效的三嗪酮杀虫活性分子,本文设计合成了16种氨基部分被取代的三嗪酮衍生物,并测试了其杀虫、抑菌活性。杀虫活性测试表明:在浓度为600mg·kg~(-1)时,化合物N-(苯基氧羰基)-N-(6-甲基-3-氧代-2,3-二氢-1,2,4-三嗪-4(5H)-基)氨基甲酸苯酯(3e,100%、100%、100%)的杀棉铃虫、玉米螟、粘虫活性高于吡蚜酮(20%,35%,50%)。在浓度为0.5mg·kg~(-1)时,化合物3e(60%)的杀蚊幼虫活性高于吡蚜酮(0)。抑菌活性测试表明:三嗪酮酰胺衍生物对玉米小斑病菌和西瓜炭疽病菌表现出较高的抑菌活性;而三嗪酮亚胺衍生物对小麦纹枯病菌表现出较高的抑菌活性。     

芳基噻唑联哌啶酰胺类化合物的合成及生物活性

为了寻找具有生物活性的新型芳香基噻唑联哌啶酰胺类先导化合物,设计并合成了15个未见文献报道的芳基噻唑联哌啶酰胺类化合物,其结构经1HNMR、13CNMR和HRMS确证,生物活性测定结果显示,部分目标化合物表现出高效的抑菌和杀虫活性,如在200μg/mL浓度下,5-(3-溴苯基)-4-甲基-2-(1-((4-硝基苯基)磺酰基)哌啶-4-基)噻唑(6b)对黄瓜霜霉病的抑菌活性为100%,优于嘧菌酯,5-(4-溴苯基)-2-(1-((4-氯苯基)磺酰基)哌啶-4-基)-4-甲基噻唑(6c)对水稻纹枯病的抑菌活性为58.86%,与嘧菌酯相当;在500μg/m L浓度下,(4-(5-(3-溴苯基)-4-甲基噻唑-2-基)哌啶-1-基)(间甲基苯基)酮(6h)对粘虫的杀虫活性为100%.     

Synthesis and Insecticidal Activities of Novel Analogues of Chlorantraniliprole Containing Nitro Group

Twelve novel analogues of chlorantraniliprole containing nitro group were synthesized,and their structures were characterized by 1H NMR and high-resolution mass spectrometry(HRMS).Their evaluated insecticidal activities against oriental armyworm(Mythimna separata) indicate that the nitro-containing analogues showed favorable insecticidal activities,while the activity of compounds 5g at 0.25mg/L was 40%,but still lower than chlorantraniliprole.     

Design,Synthesis and Biological Activities of Novel N-Aryl-1H-pyrazole-5-carboxylate Derivatives

In an attempt to search for potent fungicide, a series of novel N-aryl-1H-pyrazole-5-carboxylate derivatives was designed and synthesized. Their chemical structures were characterized by ¹H NMR spectra and high resolution mass spectrometry(HRMS). The preliminary bioassay results indicated that some target compounds displayed better fungicidal activities against certain fungi at 50 μg/mL or favorable antitumor activities at 5 μg/mLcompared with chlorothalonil and 5-fluorouracil, respectively. The structure-activity relationship demonstrated that the introduction of ester group and amide bond was favorable to the improvement of activities against Physalospora piricola and Phytophthora capsici.     

Synthesis and Biological Activities of Novel Methyl Xanthine Derivatives

Caffeine is one of methyl xanthine compounds,which has the similar mode of action as ryanodine receptor insecticide.In order to find novel and efficient insecticide,structural modification of certain methyl xanthine compounds was made by introducing some common pesticidal active moieties into the structure of caffeine.Eleven novel methyl xanthine compounds were synthesized and characterized by 1H nuclear magnetic resonance（1H NMR）,elemental analylsis or high-resolution mass spectrometry（HRMS）.According to the biological activity results,it was found that these new compounds show moderate activity towards Mythimna separata Walker and Culex pipiens pallens.For example,compound 2d shows a lethality rate of 40％ at 200 mg/L towards Mythimna separata Walker,compounds 2i and 2f show 56.7％ and 53.3％ lethality rates at 2 mg/L towards Culex pipiens pallens,which are all better than caffeine.In addition,some compounds of them show moderate antifungal activity to some plant pathogenous fungi.     

Syntheses and Biological Activities of Novel 3-Bromo-1-（3-chloropy- ridin-2-yl）-N-hydroxy-N-aryl- 1H-pyrazole-5-carboxamides

A series of novel 3-bromo-1-（3-chloropyridin-2-yl）-N-hydroxy-N-aryl-lH-pyrazole-5-carboxamides was synthesized by the reaction of pyrazole carbonyl chloride with each of substituted phenylhydroxyamines. The latter ones were prepared in good yields by reducing substituted nitrobenzene compounds with Zn/NH4CI reductant system in alcohol. Structures of the title compounds were determined by IR, 1H NMR, and HRMS. Their insecticidal and fungicidal activities were evaluated by larvicidal test against oriental armyworm and the mycelium growth rate method, respectively.     

Synthesis and Biological Evaluation of Novel Anthranilic Diamides Containing N-H/CH3-1H-Pyrazole

In order to systematically study the structure-activity relationship of anthranilic diamides and develop insecticides with simple structure and high efficiency, a series of novel anthranilic diamides containing N-H/CH₃-1H-pyrazole was designed and synthesized. Their chemical structures were characterized by ¹H NMR spectra, high resolution mass spectrometry(HRMS) or ¹³C NMR spectra. The preliminary bioassay results indicated that all title compounds displayed moderate insecticidal activity against oriental armyworm(Mythimna separata) at 200 mg/L and fungicidal activities against six kinds of fungi at 50 mg/L, especially compound 5i showed 50% insecticidal activity at 25 mg/L. In addition, some compounds exhibited certain antitumor activities. It was demonstrated that the introduction of CH₃ group into pyrazole ring was superior to H for the insecticidal activity.     

Design, Syntheses and Biological Activities of Novel Anthranilic Diamide Insecticides Containing N-Pyridylpyrazole

In search of environmentally benign insecticides with high activity, low toxicity and low residue, a series of novel anthranilic diamide derivatives containing N-pyridylpyrazole was designed and synthesized. All the compounds were characterized by ¹H NMR spectroscopy and elemental analysis. The single crystal structure of compound 8j was determined by X-ray diffraction. The insecticidal activities of the new compounds were evaluated. The results show that some compounds exhibited moderate insecticidal activities against Lepidoptera pests. Among this series of compounds, compounds 8o and 8p showed 100% larvicidal activity against Mythimna separate Walker, Plutella xylostella Linnaeus and Laphygma exigua Hubner at a test concentration of 200 mg/kg, which is equal to the commercial chlorantraniliprole.     

Design,Synthesis and Insecticidal Activities of Novel Phenyl Substituted Isoxazolecarboxamides

Thirteen novel phenyl substituted isoxazolecarboxamides were synthesized, and their structures were characterized by ¹H NMR, elementary analysis and high-resolution mass spectrometry(HRMS) techniques. Their evaluated insecticidal activities against oriental armyworm(Mythimna separata) indicate that the phenyl substituted isoxazolecarboxamides exhibited moderate insecticidal activities, among which compounds 9c and 9k showed comparatively higher activities.