CN102037964A - Application of farrerol in preparing bactericides - Google Patents
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- CN102037964A CN102037964A CN2011100042528A CN201110004252A CN102037964A CN 102037964 A CN102037964 A CN 102037964A CN 2011100042528 A CN2011100042528 A CN 2011100042528A CN 201110004252 A CN201110004252 A CN 201110004252A CN 102037964 A CN102037964 A CN 102037964A
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- DYHOLQACRGJEHX-ZDUSSCGKSA-N farrerol Chemical compound C1([C@H]2OC3=C(C)C(O)=C(C(=C3C(=O)C2)O)C)=CC=C(O)C=C1 DYHOLQACRGJEHX-ZDUSSCGKSA-N 0.000 title claims abstract 7
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- 239000003899 bactericide agent Substances 0.000 title abstract 2
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- FTNJWQUOZFUQQJ-NDAWSKJSSA-N azadirachtin A Chemical compound C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C\C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-NDAWSKJSSA-N 0.000 description 2
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- KLLYDTMVSVIJEH-YYMOATHLSA-N Rhododendrin Chemical compound C([C@@H](C)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CC1=CC=C(O)C=C1 KLLYDTMVSVIJEH-YYMOATHLSA-N 0.000 description 1
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Abstract
Description
技术领域technical field
本发明涉及一种天然化合物的用途，确切讲本发明为杜鹃素在制备杀菌剂中的应用。The present invention relates to the application of a natural compound, specifically the application of rhododendron in the preparation of fungicides.
背景技术Background technique
植物病原真菌是危害植物生长、造成植物减产的一种重要原因，同时也是影响植物籽种、茎、叶的存贮，进而影响食品安全的重要因素。现阶段化学合成的杀灭植物病原真菌药物在植物病害防治中起着不可代替的作用。但是，公众对农药毒性和农药对环境的污染问题越来越重视，一些毒性高，残留长的杀菌剂品种，如有机汞制剂和敌菌丹等相继禁用。特别在我国加入WTO后，农药残留已经成为我国农业生产和农产品出口的严重障碍。从生物体特别是植物体中寻找新的高效、低毒、低残留与环境相容性好的杀菌或抑菌活性物质，已成为当今新农药研究开发的一个热点。Phytopathogenic fungi are an important cause of harming plant growth and causing plant yield reduction, and are also an important factor affecting the storage of plant seeds, stems, and leaves, thereby affecting food safety. At present, chemically synthesized drugs for killing plant pathogenic fungi play an irreplaceable role in the control of plant diseases. However, the public pays more and more attention to the toxicity of pesticides and the pollution of pesticides to the environment. Some fungicides with high toxicity and long residue, such as organic mercury preparations and captafol, have been banned one after another. Especially after my country's accession to WTO, pesticide residues have become a serious obstacle to my country's agricultural production and export of agricultural products. Finding new bactericidal or antibacterial active substances with high efficiency, low toxicity, low residue and good environmental compatibility from organisms, especially plants, has become a hot spot in the research and development of new pesticides.
植物是生物活性化合物的天然宝库，其次生代谢产物超过40万种，其中，许多次生物质具有杀虫(或)杀菌、抑菌等生物活性，在农业、医药上有着重要的研究价值。植物性或植物源的化合物自古以来就被广泛的应用在人类的医药和农药上。最重要的三大类杀虫剂：拟除虫菊酯类，氨基甲酸酯类以及近几年迅速发展起来的新烟碱类，其合成先导化合物都是来自高等植物；而且，鱼藤酮，异羊角扭甙和印楝素等许多新的植物性杀虫剂都已经商品化。1998年，孟昭礼等从银杏中分离出对植物病原真菌有很高活性的化合物，已开发出“绿帝”农用杀菌剂系列产品。由于植物性农药来自天然，具有容易生物降解，不污染环境等优点。目前，从植物中寻找抗菌化合物并开发出植物性杀菌剂正越来越受到世界各国的重视，也是抗菌药物研制与生产单位重要的工作方向。Plants are a natural treasure house of biologically active compounds, and their secondary metabolites exceed 400,000 species. Among them, many secondary biomasses have biological activities such as insecticidal (or) bactericidal, and bacteriostatic, and have important research values in agriculture and medicine. Plant or plant-derived compounds have been widely used in human medicine and pesticides since ancient times. The three most important categories of insecticides: pyrethroids, carbamates, and neonicotinoids, which have developed rapidly in recent years, all of which are synthesized from higher plants; Many new botanical insecticides such as azadirachtin and azadirachtin have been commercialized. In 1998, Meng Zhaoli et al. isolated compounds with high activity against phytopathogenic fungi from Ginkgo biloba, and developed a series of "Ludi" agricultural fungicides. Since the botanical pesticide comes from nature, it has the advantages of easy biodegradation and no pollution to the environment. At present, the search for antibacterial compounds from plants and the development of botanical fungicides are attracting more and more attention from all over the world, and it is also an important work direction for antibacterial drug development and production units.
发明内容Contents of the invention
本发明提供一种天然化合物作为制备杀灭植物病原真菌的药物。The invention provides a natural compound as a medicine for killing plant pathogenic fungi.
本发明所指的天然化合物是杜鹃素，根据相关的试验表明，杜鹃素能有效杀灭植物病原真菌，是一种极有前景的可用于制备杀灭或抑制植物病原真菌的药物的原料。The natural compound referred to in the present invention is rhododendron. According to related experiments, rhododendron can effectively kill phytopathogenic fungi, and is a very promising raw material for preparing medicines for killing or inhibiting phytopathogenic fungi.
杜鹃素属于二氢黄酮类物质，是从海南杜鹃的地上部分分离得到的。杜鹃素的研究已经有几十年的历史，早期主要用于慢性支气管炎及抗菌作用，临床应用仍主要局限于祛痰作用。现有文献有杜鹃素用于抗肿瘤的内容，参见中国发明专利申请200910074512.1，到目前为止，关于杜鹃素是否具有抑制植物病原真菌生长及杀灭植物病原真菌的研究还没有文献报道。另外，在现有技术中已有多种杜鹃素的提取方法，例如中国发明专利申请200910032992.5就公开了一种杜鹃素的提取方法。Rhododendron belongs to dihydroflavonoids and is isolated from the aerial parts of Rhododendron hainanensis. Rhododendron has been studied for decades, and it was mainly used for chronic bronchitis and antibacterial effect in the early stage, and its clinical application is still mainly limited to expectorant effect. Existing literature has the content of rhododendron for anti-tumor, see Chinese invention patent application 200910074512.1, so far, there is no literature report on whether rhododendron can inhibit the growth of phytopathogenic fungi and kill phytopathogenic fungi. In addition, there are many extraction methods of rhododendron in the prior art, for example, Chinese invention patent application 200910032992.5 discloses a method of extracting rhododendron.
本发明的实验证明：杜鹃素对于多种植物病原真菌如低等真菌，高等真菌都有很强的离体抗菌活性，表现出较广的杀菌谱；杜鹃素尤其对西瓜枯萎病菌具有很好的抑菌作用，甚至比阳性对照的甲基托布的抑菌效果更好，且对植物无药害。研究与实验表明，杜鹃素的抑菌作用方式和机理是导致西瓜枯萎病原真菌丝畸形：分支增多，菌丝变细，菌丝中空或裂开，有较好的杀灭真菌的作用。The experiment of the present invention proves: Rhododendron has very strong antibacterial activity in vitro for various plant pathogenic fungi such as lower fungi and higher fungi, and shows a wider bactericidal spectrum; The antibacterial effect is even better than that of the positive control thiophanate-methyl, and has no phytotoxicity to plants. Studies and experiments have shown that the mode and mechanism of rhododendron's antibacterial action is to cause the deformity of the fungal filaments of the watermelon wilt pathogen: more branches, thinner hyphae, hollow or cracked mycelia, and a better effect of killing fungi.
本发明具有以下有益效果：The present invention has the following beneficial effects:
(1)杜鹃素是天然抗菌化合物，无毒，无副作用，不污染环境；(1) Rhododendron is a natural antibacterial compound, non-toxic, has no side effects, and does not pollute the environment;
(2)杜鹃素具有广谱活性，杀菌活性高，使用量低，防病效果显著；(2) Rhododendron has broad-spectrum activity, high bactericidal activity, low dosage, and remarkable disease prevention effect;
(3)杀菌作用机理独特，有助于治理生产实际上杀菌剂严重的抗药性问题；(3) The bactericidal action mechanism is unique, which helps to control the serious problem of drug resistance of fungicides in actual production;
(4)杜鹃素是天然产物，且可工业合成。今后还可以以该化合物的结构为模板，进行分子结构改造，研究其构效关系，期望得到更高活性的化合物，并将其开发成新的杀菌剂品种。(4) Rhododendron is a natural product and can be synthesized industrially. In the future, the structure of this compound can also be used as a template to carry out molecular structure modification, study its structure-activity relationship, expect to obtain a compound with higher activity, and develop it into a new type of fungicide.
具体实施方式Detailed ways
通过下面给出的本发明的具体实施例可以进一步清楚地理解发明，但下述实施例不是对本发明的限定。The invention can be further clearly understood through the specific examples of the present invention given below, but the following examples do not limit the present invention.
实施例1杜鹃素对植物病原真菌菌丝生长的抑菌活性The bacteriostasis activity of embodiment 1 rhododendron to phytopathogenic fungus mycelium growth
供试病原真菌香蕉枯萎病菌(F.oxysporum f.sp.cubense race 4)，芒果炭疽病菌(C.gloeosporioids)，黄瓜炭疽病菌(Phytophthora melonis)，柑橘青霉病菌(Penicillium italicum)，水稻纹枯病菌(Rhizoctonia solani)，西瓜枯萎病菌(Fusarium oxysporum f.sp.Niveum)。The pathogenic fungi tested were F.oxysporum f.sp.cubense race 4, C.gloeosporioids, Phytophthora melonis, Penicillium italicum, rice sheath blight Rhizoctonia solani, Fusarium oxysporum f.sp. Niveum.
实验方法采用含毒介质的生长速率法测定杜鹃素对植物病原真菌菌丝生长的抑制作用。简述为将杜鹃素用丙酮溶解后加入到熔融的PDA培养基中(丙酮含量0.4％)，分别配成含杜鹃素一定浓度的含药PDA平板。将培养活化好的直径是5mm的各病原真菌的菌丝块移到含药平板中央，每个浓度设三次重复，并设0.4％的丙酮作为对照。置25℃恒温培养。用十字交叉法测量菌落直径，并校正，计算抑菌百分率，计算毒力回归方程y＝a+bx，抑制中浓度(EC50)。Experimental method The growth rate method of toxic media was used to determine the inhibitory effect of rhododendron on the growth of phytopathogenic fungal hyphae. The brief description is that rhododendrin is dissolved in acetone and then added to molten PDA medium (acetone content: 0.4%) to form drug-containing PDA plates containing a certain concentration of rhododendron. The hyphae blocks of each pathogenic fungus with a diameter of 5mm after cultivation and activation were moved to the center of the drug-containing plate, and each concentration was repeated three times, and 0.4% acetone was set as a control. Set 25 ℃ constant temperature culture. Measure the colony diameter by the cross method, and correct it, calculate the percentage of inhibition, calculate the virulence regression equation y=a+bx, and the concentration of inhibition (EC 50 ).
实验结果Experimental results
杜鹃素对植物病原真菌菌丝生长的抑制作用测试结果见表。从表1可见杜鹃素对供试的多种植物病原真菌的菌丝生长都表现出很好的抑菌活性。其中对西瓜枯萎病菌的抑制中浓度EC50值为9μg/mL，甚至比阳性对照甲基托布津的抑制活性更好。对芒果炭疽病菌的抑制中浓度EC50为18μg/mL。The test results of the inhibitory effect of rhododendron on the growth of phytopathogenic fungus mycelium are shown in the table. It can be seen from Table 1 that Rhododendron has good antibacterial activity on the hyphal growth of various plant pathogenic fungi tested. Among them, the medium concentration EC 50 value for the inhibition of Fusarium wilt of watermelon was 9 μg/mL, even better than the inhibitory activity of the positive control thiophanate-methyl. The medium concentration EC 50 for the inhibition of mango anthracnose bacteria is 18μg/mL.
表1杜鹃素对植物病原真菌的抑制作用(EC50，μg/mL)Table 1 Inhibitory effect of rhododendron on plant pathogenic fungi (EC 50 , μg/mL)
实验例2杜鹃素对西瓜枯萎病菌抑菌作用机理观察Experimental Example 2 Observation on the Antibacterial Mechanism of Rhododendron against Fusarium wilt of Watermelon
试供病原真菌西瓜枯萎病菌Fusarium wilt of watermelon
试验方法：experiment method:
将杜鹃素制成10μg/mL含毒平板，在含毒平板上培养西瓜枯萎病原真菌，同时做对照实验挑取菌丝，在光学显微镜下观测菌丝的形态。Rhododendron was made into 10μg/mL poisonous plate, and the pathogenic fungus of watermelon wilt was cultivated on the poisonous plate. At the same time, the mycelium was picked for a control experiment, and the morphology of the mycelium was observed under an optical microscope.
试验结果test results
在杜鹃素的含毒平板上的西瓜枯萎病原真菌的菌落异常。在光学显微镜下，明显可见菌丝的形态畸形：表现为分支增多，菌丝变细，菌丝中空，裂开等现象。Abnormal colonies of watermelon wilt pathogenic fungus on rhododendron-containing plates. Under the optical microscope, the deformity of the hyphae can be clearly seen: the branching is increased, the hyphae is thinner, the hyphae is hollow, and the hyphae is cracked.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106614589A (en) * | 2016-11-13 | 2017-05-10 | 徐州得铸生物科技有限公司 | Insecticide composition containing tribulus terrestris saponins |
| CN108576083A (en) * | 2018-07-27 | 2018-09-28 | 贵州省茗之源种植专业合作社 | A kind of Chinese medicine composition and preparation method thereof preventing cucumber anthracnose |
| CN108640768A (en) * | 2018-07-27 | 2018-10-12 | 普定县景凤种养殖专业合作社 | A kind of fertilizer and preparation method thereof of prevention cucumber anthracnose |
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| CN1293900A (en) * | 2000-11-29 | 2001-05-09 | 武剑辉 | Aquatic stemonine solution as plant insecticide |
| CN1493195A (en) * | 2003-09-12 | 2004-05-05 | 李瑞金 | Insecticide, bactericide and its preparation and application method |
| CN1618293A (en) * | 2003-11-20 | 2005-05-25 | 郭伟光 | Non-pollution agricultural chemicals, and prepn. method therefor |
| WO2007006079A1 (en) * | 2005-07-08 | 2007-01-18 | Hexima Limited | Management of plant pathogens |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1111478A (en) * | 1994-11-01 | 1995-11-15 | 吴日章 | Multivariate Chinese herbal medicine plant insecticide and preparation method thereof |
| CN1293900A (en) * | 2000-11-29 | 2001-05-09 | 武剑辉 | Aquatic stemonine solution as plant insecticide |
| CN1493195A (en) * | 2003-09-12 | 2004-05-05 | 李瑞金 | Insecticide, bactericide and its preparation and application method |
| CN1618293A (en) * | 2003-11-20 | 2005-05-25 | 郭伟光 | Non-pollution agricultural chemicals, and prepn. method therefor |
| WO2007006079A1 (en) * | 2005-07-08 | 2007-01-18 | Hexima Limited | Management of plant pathogens |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106614589A (en) * | 2016-11-13 | 2017-05-10 | 徐州得铸生物科技有限公司 | Insecticide composition containing tribulus terrestris saponins |
| CN108576083A (en) * | 2018-07-27 | 2018-09-28 | 贵州省茗之源种植专业合作社 | A kind of Chinese medicine composition and preparation method thereof preventing cucumber anthracnose |
| CN108640768A (en) * | 2018-07-27 | 2018-10-12 | 普定县景凤种养殖专业合作社 | A kind of fertilizer and preparation method thereof of prevention cucumber anthracnose |
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