CN109645008B - 芦竹碱及其衍生物在抗植物病毒和病菌中的应用 - Google Patents
芦竹碱及其衍生物在抗植物病毒和病菌中的应用 Download PDFInfo
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- CN109645008B CN109645008B CN201910078373.3A CN201910078373A CN109645008B CN 109645008 B CN109645008 B CN 109645008B CN 201910078373 A CN201910078373 A CN 201910078373A CN 109645008 B CN109645008 B CN 109645008B
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Classifications
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
- A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- C—CHEMISTRY; METALLURGY
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
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Abstract
本发明芦竹碱及其衍生物在抗植物病毒和病菌中的应用，涉及含有带1个氮原子作为仅有的环杂原子的五元环杂环化合物的杀生剂，具体地说是二十三种芦竹碱及其衍生物用作抗植物病毒剂和用作杀植物病原真菌剂，所述用作抗植物病毒剂是用于烟草花叶病毒、辣椒病毒、水稻病毒、番茄病毒、甘薯病毒、马铃薯病毒、瓜类病毒及玉米矮花叶病毒；所述用作杀植物病原真菌剂是用于抑制黄瓜枯萎，花生褐斑，苹果轮纹，小麦纹枯，玉米小斑，西瓜炭疽，水稻恶苗，番茄早疫，小麦赤霉，马铃薯晚疫，辣椒疫霉，油菜菌核，黄瓜灰霉，水稻纹枯14种植物病菌。
Description
技术领域
本发明的技术方案涉及含有带1个氮原子作为仅有的环杂原子的五元环杂环化合物的杀生剂，具体地说是芦竹碱及其衍生物在抗植物病毒和病菌中的应用。
背景技术
芦竹碱为天然的含有吲哚骨架的生物碱，其基本结构骨架为叔胺结构和吲哚结构，其化学结构式如下：
芦竹碱有极高的生物活性。在自然界中广泛分布，是小麦、大麦和芦竹等禾本植物在进化过程中产生的具有化感作用的一种生物碱(Phytochemistry,1984,23(3),539–541；Phytochemistry,1985,24(5),945–947；Exp.Appl.,1986,40(3),259–262.)，对环境植物、昆虫、微生物等具有生长抑制作用(邵阳学院学报,2003,2(2),131–135.)。人们利用芦竹碱不同的生物活性，开发不同用途的生物农药。如大麦分泌的芦竹碱对蘩缕属杂草具有很强的抑制作用(世界农业,2002,279(7),41–44.)，10mg/Kg浓度即对其生长具有77％的抑制作用，可被开发为生物除草剂(J.Org.Chem.,1959,24,1285–1287.)。芦竹碱使昆虫产生拒食性(昆虫知识,2003,40(1),24–27；沈阳农业大学学报,2002,33(4),309–314.)，可开发相关农药用于作物杀虫剂。芦竹碱及其衍生物因其高效、低毒、抵抗性、低残留的特点，使其成为一位具有广泛开发前景的生物农药(农药,2004,43(2),76–77)。
芦竹碱在大麦中的浓度大约8mg/g(干重)，因此在生长过程中对害虫有一定的抵御作用，但是它对哺乳动物有一定的毒副作用(Plant Physiol.1983,71,896–904；Pharm.Chem.J.2004,38,287–310；Mat.Sci.Eng.C 2016,65,400–407.)，因此通过对其结构的修饰和改造来提高活性并降低对环境的毒性，具有非常重要的应用价值。
鉴于芦竹碱及其衍生物具有广泛开发前景，现今科技人员对芦竹碱及其衍生物的应用的研发仍是方兴未艾。
发明内容
本发明所要解决的技术问题是：提供芦竹碱及其衍生物在抗植物病毒和病菌中的应用，首次发现芦竹碱及其衍生物具有很好的抗植物病毒和病菌活性，扩大了芦竹碱及其衍生物作为生物农药的应用范围。
本发明解决该技术问题所采用的技术方案是：芦竹碱及其衍生物在抗植物病毒和病菌中的应用，具体地说是以下1～23种化学结构式所示的芦竹碱及其衍生物用作抗植物病毒剂和用作杀植物病原真菌剂，
其中，化学结构式1所示的化合物为芦竹碱，化学结构式2所示的芦竹碱衍生物为5-溴芦竹碱，化学结构式3所示的芦竹碱衍生物为6-溴芦竹碱，化学结构式4所示的芦竹碱衍生物为3-((4-甲氧基苯基)(1-吡咯烷基)甲基)-1H-吲哚，化学结构式5所示的芦竹碱衍生物为3-(苯基(1-吡咯烷基)甲基)-1H-吲哚，化学结构式6所示的芦竹碱衍生物为3-(环己基(1-吡咯烷基)甲基)-1H-吲哚，化学结构式7所示的芦竹碱衍生物为1-(2,4-二甲氧基苯基)-1-(1H-吲哚-3-基)-N,N-二甲基甲胺，化学结构式8所示的芦竹碱衍生物为3-((4-氟苯基)(1-吡咯烷基)甲基)-1H-吲哚，化学结构式9所示的芦竹碱衍生物为3-(1-吡咯烷基(3,4,5-三甲氧基苯基)甲基)-1H-吲哚，化学结构式10所示的芦竹碱衍生物为3-((4-硝基苯基)(1-吡咯烷基)甲基)-1H-吲哚，化学结构式11所示的芦竹碱衍生物为3-((2-溴苯基)(1-吡咯烷基)甲基)-1H-吲哚，化学结构式12所示的芦竹碱衍生物为N-((1H-吲哚-3-基)(苯基)甲基)吡啶-2-胺，化学结构式13所示的芦竹碱衍生物为N-((1H-吲哚-3-基)(3,4,5-三甲氧基苯基)甲基)吡啶-2-胺，化学结构式14所示的芦竹碱衍生物为N-((1H-吲哚-3-基)(4-甲氧基苯基)甲基)吡啶-2-胺，化学结构式15所示的芦竹碱衍生物为N-((1H-吲哚-3-基)(4-硝基苯基)甲基)吡啶-2-胺，化学结构式16所示的芦竹碱衍生物为N-((1H-吲哚-3-基)(4-三氟甲基苯基)甲基)吡啶-2-胺，化学结构式17所示的芦竹碱衍生物为N-(环己基(1H-吲哚-3-基)甲基)吡啶-2-胺，化学结构式18所示的芦竹碱衍生物为N-((1H-吲哚-3-基)(苯基)甲基)吡啶-2-胺，化学结构式19所示的芦竹碱衍生物为3-((1H-嘧啶-1-基)(苯基)甲基)-1H-吲哚，化学结构式20所示的芦竹碱衍生物为N-((1H-吲哚-3-基)(苯基)甲基)苯胺，化学结构式21所示的芦竹碱衍生物为1-甲基芦竹碱，化学结构式22所示的芦竹碱衍生物为1-甲基-5-溴芦竹碱，化学结构式23所示的芦竹碱衍生物为1-丁基-5-溴芦竹碱。
上述芦竹碱及其衍生物在抗植物病毒和病菌中的应用，所述用作抗植物病毒剂是用于烟草花叶病毒、辣椒病毒、水稻病毒、番茄病毒、甘薯病毒、马铃薯病毒、瓜类病毒及玉米矮花叶病毒。
上述芦竹碱及其衍生物在抗植物病毒和病菌中的应用，所述用作杀植物病原真菌剂是用于抑制黄瓜枯萎，花生褐斑，苹果轮纹，小麦纹枯，玉米小斑，西瓜炭疽，水稻恶苗，番茄早疫，小麦赤霉，马铃薯晚疫，辣椒疫霉，油菜菌核，黄瓜灰霉，水稻纹枯14种植物病菌。
本发明的有益效果是：与现有技术相比，本发明具有的突出的实质性特点和显著进步如下：
本发明首次发现芦竹碱及其衍生物具有很好的抗植物病毒和病菌活性，扩大了芦竹碱及其衍生物作为生物农药的应用范围。
具体实施方式
实施例1
本发明的以下1～23种化学结构式所示的芦竹碱及其衍生物由参照现有文献(Synth.Commun.2006,36(13),1829–1835；Tetrahedron Lett.2014,55,2977–2981.)所公开的方法制备，
其中，
化学结构式1所示的化合物为芦竹碱，
化学结构式2所示的芦竹碱衍生物为5-溴芦竹碱，
化学结构式3所示的芦竹碱衍生物为6-溴芦竹碱，
化学结构式4所示的芦竹碱衍生物为3-((4-甲氧基苯基)(1-吡咯烷基)甲基)-1H-吲哚，
化学结构式5所示的芦竹碱衍生物为3-(苯基(1-吡咯烷基)甲基)-1H-吲哚，
化学结构式6所示的芦竹碱衍生物为3-(环己基(1-吡咯烷基)甲基)-1H-吲哚，
化学结构式7所示的芦竹碱衍生物为1-(2,4-二甲氧基苯基)-1-(1H-吲哚-3-基)-N,N-二甲基甲胺，
化学结构式8所示的芦竹碱衍生物为3-((4-氟苯基)(1-吡咯烷基)甲基)-1H-吲哚，
化学结构式9所示的芦竹碱衍生物为3-(1-吡咯烷基(3,4,5-三甲氧基苯基)甲基)-1H-吲哚，
化学结构式10所示的芦竹碱衍生物为3-((4-硝基苯基)(1-吡咯烷基)甲基)-1H-吲哚，
化学结构式11所示的芦竹碱衍生物为3-((2-溴苯基)(1-吡咯烷基)甲基)-1H-吲哚，
化学结构式12所示的芦竹碱衍生物为N-((1H-吲哚-3-基)(苯基)甲基)吡啶-2-胺，
化学结构式13所示的芦竹碱衍生物为N-((1H-吲哚-3-基)(3,4,5-三甲氧基苯基)甲基)吡啶-2-胺，
化学结构式14所示的芦竹碱衍生物为N-((1H-吲哚-3-基)(4-甲氧基苯基)甲基)吡啶-2-胺，
化学结构式15所示的芦竹碱衍生物为N-((1H-吲哚-3-基)(4-硝基苯基)甲基)吡啶-2-胺，
化学结构式16所示的芦竹碱衍生物为N-((1H-吲哚-3-基)(4-三氟甲基苯基)甲基)吡啶-2-胺，
化学结构式17所示的芦竹碱衍生物为N-(环己基(1H-吲哚-3-基)甲基)吡啶-2-胺，
化学结构式18所示的芦竹碱衍生物为N-((1H-吲哚-3-基)(苯基)甲基)吡啶-2-胺，
化学结构式19所示的芦竹碱衍生物为3-((1H-嘧啶-1-基)(苯基)甲基)-1H-吲哚，
化学结构式20所示的芦竹碱衍生物为N-((1H-吲哚-3-基)(苯基)甲基)苯胺，
化学结构式21所示的芦竹碱衍生物为1-甲基芦竹碱，
化学结构式22所示的芦竹碱衍生物为1-甲基-5-溴芦竹碱，
化学结构式23所示的芦竹碱衍生物为1-丁基-5-溴芦竹碱。
实施例2
上述1～23种化学结构式所示的芦竹碱及其衍生物的个体化合物用作抗植物病毒剂：
上述1～23种化学结构式所示的芦竹碱及其衍生物的个体化合物的抗烟草花叶病毒活性的测定，测定程序如下：
第一步，烟草花叶病毒提纯及浓度测定：
烟草花叶病毒提纯及浓度测定参照南开大学元素所生测室编制烟草花叶病毒SOP规范执行，病毒粗提液经2次聚乙二醇离心处理后，测定浓度为20μg/mL，4℃冷藏备用；
第二步，上述1～23种化学结构式所示的芦竹碱及其衍生物的个体化合物药剂溶液的配制：
分别称量上述1～23种化学结构式所示的芦竹碱及其衍生物的个体化合物40mg作为原药，然后分别在该各种原药中加入DMF 0.4mL进行溶解，制得1×105μg/mL母液，再用质量百分比浓度为1‰的吐温80水溶液稀释至测试浓度为500μg/mL或100μg/mL，由此分别配制得上述1～23种化学结构式所示的芦竹碱及其衍生物的个体化合物药剂溶液，另外取宁南霉素制剂直接兑水稀释作为对比物；
第三步，离体作用：
分别配置二十三份摩擦接种3–5叶期珊西烟叶片，分别用流水冲洗，病毒浓度为10μg/mL，收干后剪下，沿叶中脉对剖，左右半叶分别浸于质量百分比浓度为1‰的吐温80水溶液及第二步配制得的上述1～23种化学结构式所示的芦竹碱及其衍生物的个体化合物的药剂溶液中，30min后取出，于常温光照条件下保湿培养，每3片叶为1次重复，重复3次，3天后记录病斑数，计算防效；
第四步，活体保护作用：
分别选二十三棵长势均匀一致的3–5叶期珊西烟，每单科全株珊西烟分别喷雾施上述第二步配制得的上述1～23种化学结构式所示的芦竹碱及其衍生物的个体化合物药剂溶液，每处理3次重复，并设置质量百分比浓度为1‰的吐温80水溶液对照，24h后，叶面撒布500目金刚砂，用毛笔蘸取病毒液，在全叶面沿支脉方向轻擦2次，叶片下方用手掌支撑，病毒浓度10μg/mL，接种后用流水冲洗，3天后记录病斑数，计算防效；
第五步，活体治疗作用：
分别选二十三棵长势均匀一致的3–5叶期珊西烟，分别用毛笔全叶接种病毒，病毒浓度为10μg/mL，接种后用流水冲洗，叶面收干后，二十三棵珊西烟分别全株喷雾施上述第二步配制得的上述1～23种化学结构式所示的芦竹碱及其衍生物的个体化合物药剂溶液，每处理3次重复，并设置质量百分比浓度为1‰的吐温80水溶液对照，3天后记录病斑数，计算防效；
第六步，活体钝化作用：
分别选二十三棵长势均匀一致的3–5叶期珊西烟，将上述第二步配制得的上述1～23种化学结构式所示的芦竹碱及其衍生物的个体化合物药剂溶液分别与等体积的病毒汁液混合钝化30min后，分别摩擦接种，病毒浓度为20μg/mL，接种后即用流水冲洗，重复3次，设置质量百分比浓度为1‰的吐温80水溶液对照，3天后数病斑数，计算结果；
上述1～23种化学结构式所示的芦竹碱及其衍生物的个体化合物的抗烟草花叶病毒活性的测定结果见表1。
抑制率(％)＝[(对照枯斑数-处理枯斑数)/对照枯斑数]×100％
表1.上述1～23种化学结构式所示的芦竹碱及其衍生物的个体化合物的抗烟草花叶病毒活性的测定结果
从表1中可见上述1～23种化学结构式所示的芦竹碱及其衍生物的个体化合物表现出很好的抗TMV活性，离体测试中化合物2、6、7～9、11、14、16～17、21～22抗TMV均超过了商品化品种病毒唑；化合物3、4和13在活体测试，即活体钝化、活体治疗和活体保护中，抗TMV也均超过了病毒唑；特别是化合物7、14和22抗TMV与商品化品种宁南霉素相当，具备极大的开发价值。
实施例3
上述1～23种化学结构式所示的芦竹碱及其衍生物的个体化合物用作杀植物病原真菌剂，
A.离体杀菌测试，菌体生长速率测定法(平皿法)：
上述1～23种化学结构式所示的芦竹碱及其衍生物的个体化合物的抗菌活性测试，离体杀菌测试，测定程序如下：
菌体生长速率测定法即平皿法：分别将上述1～23种化学结构式所示的芦竹碱及其衍生物的个体化合物各3mg溶解在0.03mL丙酮内，然后用含有200μg/mL吐温80的水溶液稀释至测试浓度为50mg/kg，然后各吸取1mL药液注入与之对应的培养皿内，再分别加入9mL培养基，摇匀后制成50μg/mL的含药平板，以添加1mL灭菌纯净水的平板做空白对照，用直径4mm的打孔器沿菌丝外缘切取菌盘，移至上述含药平板上，每处理重复三次，将培养皿放在24±1℃恒温培养箱内培养，48h后调查各处理菌盘扩展直径，求平均值，与空白对照比较计算相对抑菌率。
上述1～23种化学结构式所示的芦竹碱及其衍生物的个体化合物的离体杀真菌活性的结果见表2。
表2.上述1～23种化学结构式所示的芦竹碱及其衍生物的个体化合物的离体杀真菌活性的结果
由表2中数据可以看出，上述1～23种化学结构式所示的芦竹碱及其衍生物的个体化合物的表现出很好的抗植物病菌活性，化合物16对苹果轮纹抑制率达到90％以上。化合物23对番茄早疫、辣椒疫霉和苹果轮纹的抑制率均达到了50％以上，具有广谱的杀菌活性。
B.活体杀菌测试，植株喷雾法：
上述1～23种化学结构式所示的芦竹碱及其衍生物的个体化合物的抗菌活性测试，活体杀菌测试，植株喷雾法，测定程序如下：
分别称量各个上述1～23种化学结构式所示的芦竹碱及其衍生物的个体化合物，定量DMSO溶解后加入1‰吐温80水溶液，分别配制成二十三种所需浓度待测液，分别进行以下试验操作，
供试黄瓜、小麦、油菜、辣椒幼苗培养于南开大学生测楼日光温室，黄瓜和辣椒第一片真叶完全展开后，分别喷雾上述待测液处理，喷液量1mL/处理，喷雾压力0.7kg/cm2，喷雾距离15cm，小麦和油菜一叶一心期处理，方法与黄瓜处理过程相同。
药剂处理后24h，黄瓜灰霉与黄瓜褐斑均采用喷雾接种5×105个/mL的孢子囊悬浮液于药剂处理后的黄瓜真叶叶背，至叶片呈水浸状止。暗环境保湿培养24h，后移至温室环境下正常培养。48h后调查结果。小麦苗则采用沉降接种法，接菌后7d调查结果。结果调查采用分级方法，以“100”级代表无病，即抑制率100％；“0”级代表最严重的发病程度，抑制率为0，记录。
表3.上述1～23种化学结构式所示的芦竹碱及其衍生物的个体化合物的活体杀菌活性测试结果
从表3中数据可以看出，上述1～23种化学结构式所示的芦竹碱及其衍生物的个体化合物表现出很好的活体杀菌活性。
上述实施例中的百分比均为质量百分比。
上述实施例中所涉及的原料和试剂均由商购获得，操作方法是本领域技术人员所能掌握的。
Claims (3)
1.芦竹碱衍生物在抗植物病毒和病菌中的应用，其特征在于：具体地说是以下化学结构式所示的1-甲基-5-溴芦竹碱用作抗植物病毒剂和用作杀植物病原真菌剂，
2.根据权利要求1所述芦竹碱衍生物在抗植物病毒和病菌中的应用，其特征在于：所述用在抗植物病毒中的应用是用于抗烟草花叶病毒、辣椒病毒、水稻病毒、番茄病毒、甘薯病毒、马铃薯病毒、瓜类病毒及玉米矮花叶病毒。
3.根据权利要求1所述芦竹碱衍生物在抗植物病毒和病菌中的应用，其特征在于：所述用作杀植物病原真菌剂中的应用，是用于抑制黄瓜枯萎、花生褐斑、苹果轮纹、小麦纹枯、玉米小斑、西瓜炭疽、水稻恶苗、番茄早疫、马铃薯晚疫、辣椒疫霉、黄瓜灰霉、水稻纹枯12种植物病菌。
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| Biological properties of alkaloids. Influence of quinolizidine alkaloids and gramine on the germination and development of powdery mildew, Erysiphe graminis f.sp. hordei;C. Wippich等;《Experientia》;19851231;第41卷;第1477-1479页 * |
| 新型植物源农药卢竹碱的应用与合成研究;许前会等;《农药》;20040228;第43卷(第2期);第76和77页 * |
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