WO2023019821A1 - 一种嗜氮酮类多聚体化合物及其制备方法和应用 - Google Patents

一种嗜氮酮类多聚体化合物及其制备方法和应用 Download PDF

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WO2023019821A1
WO2023019821A1 PCT/CN2021/137672 CN2021137672W WO2023019821A1 WO 2023019821 A1 WO2023019821 A1 WO 2023019821A1 CN 2021137672 W CN2021137672 W CN 2021137672W WO 2023019821 A1 WO2023019821 A1 WO 2023019821A1
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preparation
methanol
compound
azone
fraction
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元超
于福来
王丹
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中国热带农业科学院热带作物品种资源研究所
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/76—Benzo[c]pyrans
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/14—Fungi; Culture media therefor
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/02—Oxygen as only ring hetero atoms
    • C12P17/06—Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
    • Y02A40/10—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in agriculture

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  • the invention relates to the technical field of medicinal chemistry, in particular to an azone-like multimer compound, a preparation method and application thereof.
  • Weeds mainly refer to plants that are unfavorable to human activities or harmful to crop growth, generally herbaceous plants. Weeds compete with crops for nutrients, water, light and space, and spread pests and diseases, thereby reducing crop yield and quality.
  • Weed control methods mainly include physical weeding, chemical weeding and biological weeding, etc. Among them, chemical weeding is the mainstream method of weed control because of its high efficiency, timely, labor-saving and economical characteristics.
  • herbicides can be divided into selective herbicides (harmful to some weeds) and non-selective herbicides (toxic to all plants, such as glyphosate).
  • Classified by chemical composition herbicides are divided into inorganic herbicides and organic herbicides (ethers, triazines, substituted ureas, phenoxyacetic acids, pyridines, dinitroanilines, organophosphorus, Amides and phenols, etc.).
  • herbicides are divided into photosynthesis inhibitors, amino acid biosynthesis inhibitors, fatty acid biosynthesis inhibitors and cell division inhibitors. Many herbicides have been proven to have good weed control effects. However, with the long-term and extensive use of chemical herbicides, the problem of weed resistance is becoming more and more serious. Therefore, it is urgent to develop new and efficient herbicides.
  • Azotropes are a class of compounds discovered from fungi that contain a highly oxidized pyronephenoquinone bicyclic ring and a chiral quaternary carbon center. Studies have shown that azone compounds have a wide range of biological activities, including cytotoxicity, antitumor activity, antibacterial activity and so on. At present, some research progress has been made on the structure and activity of azone compounds, but there are still a large number of novel structures that have not been discovered, and the research on azone compounds in weed control has not been reported.
  • the purpose of the present invention is to provide a nitrogenophilic ketone polymer compound and its preparation method and application.
  • a nitrogenophilic ketone polymer compound its structural formula is as shown in the following formula I:
  • the preparation method of the azone-like multimer compound comprises the following steps:
  • the above-mentioned fungus muyocopron laterale can be isolated from plants such as Aina chinensis by conventional methods, and can also be obtained from relevant depository institutions.
  • Known strains of muyocopron laterale include CBS 719.95, CBS 145311, CBS 145312, and CBS 145316 of Centraalbureau Voor Schimmelcultures in the Netherlands, and Gene Resource Preservation Center (International Mycological Institute, International Mycological Institute, International Center for Agriculture and Biology, UK). IMI 324533 of the CABI Genetic Resource Collection).
  • the volume ratio of methanol-water is 70:30.
  • the chromatographic column model of the semi-preparative liquid chromatography is: YMC-Pack ODS-A.
  • the culture medium is mixed with 80 mL of water per 60 g of rice.
  • the fraction Fr.B is a fraction obtained by eluting with dichloromethane-methanol at a volume ratio of 99:1.
  • the fermentation culture condition is: static culture at 28° C. for 30 days.
  • the Sephadex LH-20 is Sephadex LH-20.
  • the present invention also provides the application of the azone-like multimer compound in controlling weeds. More specifically, the azone-like multimer compound can achieve the weed control effect by inhibiting the growth of plant roots.
  • the present invention separates an azone-like polymer compound from the fermentation product of the endophytic fungus muyocopron laterale.
  • the azone-like compound has a novel structural skeleton and belongs to a new type of azone-like compound.
  • the present invention ferments and cultures muyocopron laterale, and separates the fermentation product to obtain high-purity compound monomers.
  • the preparation method provided by the invention is simple and efficient.
  • the present invention finds that the obtained compound has a strong effect of inhibiting plant root elongation, and can be used as a new generation of herbicide active ingredient.
  • PDA 200g potato, 20g glucose, 15g agar, 1000mL water, sterilized at 121°C for 20min.
  • the rice fermentation product of the fungus muyocopron laterale was ultrasonically extracted 3 times with ethyl acetate, 30 min each time, and concentrated to dryness under reduced pressure to obtain 20.3 g of total extract of secondary metabolites.
  • the total extract was dissolved in methanol, mixed with silica gel in a ratio of 1/3, and subjected to silica gel column chromatography, the elution system was dichloromethane-methanol (100/0, 99/1, ..., 1/1, V/V), 8 fractions A(100/0), B(100/0), C(99/1), D(99/1), E(98/2), F(20/1), G(10 /1), H(1/1).
  • Fr.A-Fr.G Fr.A-Fr.G were obtained.
  • Compound 1 can also be obtained by selecting the fungus muyocopron laterale obtained from the depository institution for the above fermentation and extraction.
  • Embodiment 2 Structural identification of compound 1
  • the structure of compound 1 was analyzed by using spectroscopy, spectroscopy and other structural identification techniques.
  • H-1 ( ⁇ H 7.45) and C-3 ( ⁇ C 160.7), C-4a ( ⁇ C 143.7 ), C-8a ( ⁇ C 120.8), C-8 ( ⁇ C 71.7), H-4 ( ⁇ H 6.39) is related to C-9 ( ⁇ C 18.5), C-3 ( ⁇ C 160.7), C- 4a (143.7), C-5 ( ⁇ C 109.3), C-8a ( ⁇ C 120.8), H-8 ( ⁇ H 4.46) correlated with C-1 ( ⁇ C 144.9), C-6 ( ⁇ C 197.7) , C-7 ( ⁇ C 76.4), C-4a, and C-8a are correlated, and the detection of carbon signals in the middle and low fields shows that they all appear in pairs, a total of
  • HMBC spectrum analysis shows that H-17 ( ⁇ H 1.88) is related to C-12 ( ⁇ C 155.5), C-13 ( ⁇ C 154.3), C-14 ( ⁇ C 206.2), H-18 ( ⁇ H 1.11) Related to C-15 ( ⁇ C 49.8), C-14 ( ⁇ C 206.2), C-16 ( ⁇ C 205.9) and C-11' ( ⁇ C 30.2), suggesting a five-membered ⁇ , ⁇ unsaturated ring the presence of diketones.
  • H-11 ( ⁇ H 3.41) is related to C-12, C-13, C-16, C-4a, C-5, C-6, suggesting that the C-12 position of the five-membered ring is passed
  • One CH2 is linked to the C-5 position of one of the Azaphilone fragments.
  • Embodiment 3 Root elongation inhibition experiment
  • Example 1 The seeds of Arabidopsis thaliana, a cruciferous Arabidopsis plant, were sterilized with 5% sodium hypochlorite solution, rinsed with sterile water, and dried.
  • Compound 1 obtained in Example 1 was prepared with dimethyl sulfoxide (DMSO) into a mother solution with a final concentration of 40 mg/mL for later use; the mother solution was absorbed and added to 25 mL of 1/2 MS medium to make the concentration of compound 1 respectively 8 ⁇ g/mL , 16 ⁇ g/mL, and 32 ⁇ g/mL were used as treatment groups. Add 20 ⁇ L of DMSO as blank control group. Five seeds with consistent growth were evenly added to each plate, and three parallel experiments were set up in each group. Each group of plates was cultured in a constant temperature (23 ⁇ 1°C) culture room, and the photoperiod L/D was 18h/6h. After 9 days, the root growth of each group was observed. The results are shown in Figure 6.

Abstract

本发明提供一种嗜氮酮类多聚体化合物及其制备方法和应用。本发明对muyocopronlaterale进行发酵培养，并对发酵产物进行分离，获得高纯度化合物单体，该化合物具有新颖的结构骨架，其结构为式（I）。经实验发现，该化合物具有强的抑制植物根系伸长功效，可作为新一代的除草剂活性成分。

Description

一种嗜氮酮类多聚体化合物及其制备方法和应用 技术领域
本发明涉及药物化学技术领域，具体涉及一种嗜氮酮类多聚体化合物及其制备方法和应用。
背景技术
杂草主要是指对人类活动不利或有害于作物生长的植物，一般为草本植物。杂草与作物竞争养分、水分、光照和空间，传播病虫害，从而降低作物的产量和品质。杂草的防治手段主要包括物理除草、化学除草和生物除草等，其中，化学除草因高效、及时、省工、经济等特点，是目前杂草防除的主流手段。
按作用方式分类，除草剂可以分为选择性除草剂(对部分杂草有害)和非选择性除草剂(对所有植物都有毒性，如草甘膦)。按化学成分分类，除草剂分为无机类除草剂和有机类除草剂(醚类、均三氮苯类、取代脲类、苯氧乙酸类、吡啶类、二硝基苯胺类、有机磷类、酰胺类和酚类等)。按作用机理分类，除草剂分为光合作用抑制剂、氨基酸生物合成抑制剂、脂肪酸生物合成抑制剂和细胞分裂抑制剂等。许多除草剂经实践证实具有很好的杂草防除效果，然而随着化学除草剂的长期大量使用，杂草的耐药性问题日益严重，因此急需研发新型高效的除草剂。
嗜氮酮是从真菌中发现的一类化合物，含有一个高度氧化的吡喃酮并苯醌双环和一个手性季碳中心。有研究显示，嗜氮酮类化合物具有广泛的生物活性，包括细胞毒性、抗肿瘤活性、抗菌活性等。目前，嗜氮酮类化合物的结构及活性已经取得一定的研究进展，但仍有大量新颖结构未被发现，嗜氮酮类化合物在杂草防除方面的研究未见报道。
发明内容
针对现有技术存在的不足，本发明的目的在于提供一种嗜氮酮类多聚体化合物及其制备方法和应用。
本发明技术方案主要包括以下内容：
一种嗜氮酮类多聚体化合物，其结构式如以下式I所示：
Figure PCTCN2021137672-appb-000001
所述嗜氮酮类多聚体化合物的制备方法，包括以下步骤：
(1)将真菌muyocopron laterale接种于培养基中发酵培养，得发酵产物，发酵产物用乙酸乙酯超声提取，减压浓缩至干，得总浸膏；
(2)总浸膏用甲醇溶解，进行硅胶柱层析，洗脱系统为体积比100:0～1:1的二氯甲烷-甲醇溶液，经TLC检测合并，共得到7个馏分Fr.A～Fr.G；
(3)馏分Fr.B经葡聚糖凝胶色谱柱分离，用甲醇等度洗脱，所得馏分通过半制备液相色谱仪进行分离，以甲醇-水为流动相，得权利要求1所述嗜氮酮类多聚体化合物。
上述真菌muyocopron laterale可以按常规方法从艾纳香等植物中分离而得，也可以从相关保藏机构获得。已知的muyocopron laterale菌株包括荷兰微生物菌种保藏中心(Centraalbureau Voor Schimmelcultures)的CBS 719.95、CBS 145311、CBS 145312、CBS 145316，英国国际真菌研究所国际农业与生物中心基因资源保藏中心(International Mycological Institute，CABI Genetic Resource Collection)的IMI 324533。
优选的，所述步骤(3)中，甲醇-水的体积比为70:30。
优选的，半制备液相色谱的色谱柱型号为：YMC-Pack ODS-A。
优选的，所述培养基由每60g大米加80mL水混合而成。
优选的，所述馏分Fr.B为经体积比99:1的二氯甲烷-甲醇洗脱所得的馏分。
优选的，发酵培养条件为：28℃静置培养30d。
优选的，所述葡聚糖凝胶色谱柱为Sephadex LH-20。
另一方面，本发明还提供了所述嗜氮酮类多聚体化合物在防治杂草中的应用。更具体的，所述嗜氮酮类多聚体化合物能够通过抑制植物根系生长而达到杂草防除效果。
本发明所取得的效果：
(1)本发明从植物内生真菌muyocopron laterale的发酵产物中分离得到一种嗜氮酮类多聚体化合物，该嗜氮酮类化合物具有新颖的结构骨架，属于新的嗜氮酮类化合物。
(2)本发明对muyocopron laterale进行发酵培养，并对发酵产物进行分离，获得高纯度化合物单体。本发明所提供的制备方法简单高效。
(3)本发明研究发现，所得化合物具有很强的抑制植物根系伸长功效，可作为新一代的除草剂活性成分。
附图说明
图1：化合物1的1H NMR谱图
图2：化合物1的13C NMR谱图
图3：化合物1的HSQC谱图
图4：化合物1的HMBC谱图
图5：化合物1的HRESIMS谱图
图6：实施例3结果图
具体实施方式
为了更好理解本发明技术内容，下面提供具体实施例，对本发明做进一步的说明。
仪器和试剂：
核磁共振波谱仪(BrukerAvance 500MHz)；
质谱仪(Waters Synapt G2，USA)；
Waters 2489半制备液相色谱系统(Waters Corporation，Milford，MA，USA)；
半制备色谱柱YMC-Pack ODS-A(5μm，250mm10mm，北京慧德易科技有限责任公司)；
200～300目柱层析硅胶和GF 254薄层硅胶板(青岛海洋化工厂)；
PDA：马铃薯200g，葡萄糖20g，琼脂15g，水1000mL，121℃灭菌20min。
实施例1-嗜氮酮类多聚体化合物的提取
(1)采集艾纳香根，自来水冲洗干净，切段，超净台上，70％乙醇消毒1min，再用3M的次氯酸钠处理3min，70％乙醇消毒30s，无菌水洗净，平放在水琼脂培养基上(15g琼脂，1000mL水，100mg链霉素，121℃高压蒸汽灭菌20min，超净工作台上倒平板)25℃培养箱培养2周，挑出断面长出的菌丝，接种到PDA培养基上，即可。经鉴定，该真菌为muyocopron laterale，属于粘菌科(Muyocopronaceae)中的一种子囊菌(ascomycete)。
(2)将真菌muyocopron laterale接种到直径6cm的无菌PDA平板培养基上，28℃培养5d，至菌落布满整个培养基平板，无菌条件下切成约0.5cm×0.5cm的组织块备用。将60g大米和80mL水加入500mL的三角瓶中，锡箔纸包扎，121℃高压蒸汽灭菌20min，取出并置于室温条件下，备用。将带菌的培养基块在无菌条件下接种至大米培养基中，每瓶2～3块，28℃静置培养30d，乙酸乙酯终止发酵。
(3)将真菌muyocopron laterale的大米发酵产物用乙酸乙酯超声提取3次，30min/次，减压浓缩至干，得次生代谢产物总浸膏20.3g。总浸膏用甲醇溶解，按照1/3比例拌硅胶，进行硅胶柱层析，洗脱系统为二氯甲烷-甲醇(100/0，99/1，…，1/1，V/V)，依次获得8个馏分A(100/0)、B(100/0)、C(99/1)、D(99/1)、E(98/2)、F(20/1)、G(10/1)、H(1/1)。TLC检测合并，共得到7个馏分Fr.A-Fr.G。Fr.B(6.2g，二氯甲烷：甲醇＝99:1)经Sephadex LH-20色谱柱，以甲醇洗脱，共得到2个馏分，其中第2个馏分(RO-B-2，90mg)通过半制备液相色谱仪进行分离，以甲醇-水(70:30,v/v)为流动相，分离得化合物1(22.1mg,tR＝11.2min,流速为2mL/min)。
选择从保藏机构获得的真菌muyocopron laterale进行上述发酵、提取亦可得到化合物1。
实施例2：化合物1的结构鉴定
运用光谱、波谱等结构鉴定技术对化合物1的结构进行分析。
化合物结构解析：
橘红色粉末，HR-ESI-MS给出离子峰m/z 565.2069[M+H] +,587.1885[M+Na] +,计算值为565.2066,587.1885，确定分子式为C 31H 32O 10。 13C NMR谱显示了31个碳信号(包括4个重叠的高场信号)，结合 1HNMR和HSQC谱可知该结构中含有6个甲基，2个亚甲基，6个次甲基，17个季碳(包括4个羰基碳，δ C 206.2,205.9,198.3,197.7),HMBC谱中，H-1(δ H 7.45)与C-3(δ C 160.7),C-4a(δ C 143.7),C-8a(δ C 120.8),C-8(δ C 71.7)相关，H-4(δ H 6.39)与C-9(δ C 18.5),C-3(δ C 160.7),C-4a(143.7),C-5(δ C 109.3),C-8a(δ C 120.8)相关,H-8(δ H 4.46)与C-1(δ C 144.9),C-6(δ C 197.7),C-7(δ C 76.4),C-4a,C-8a相关，对中低场的碳信号检测发现，均为成对出现，共11对，以上分析显示结构中可能存在两个对称的azaphilone结构片段。HMBC谱分析显示，H-17(δ H 1.88)与C-12(δ C 155.5),C-13(δ C 154.3),C-14(δ C 206.2)相关，H-18(δ H 1.11)与C-15(δ C 49.8),C-14(δ C 206.2),C-16(δ C 205.9)和C-11’(δ C 30.2)相关，提示了一个五元α,β不饱和环二酮的存在。进一步的HMBC相关分析，H-11(δ H 3.41)与C-12,C-13,C-16,C-4a,C-5,C-6相关，提示五元环的C-12位通过一个CH 2与其中一个Azaphilone片段的C-5位相连。HMBC相关谱中的H-11’(δ H 2.68,2.49)与C-14,C-15,C-16,C-18(δ C 17.3),C-4’a(δ C 144.5),C-5’(δ C 109.1),C-6’(δ C 198.3)相关，显示五元环的C-15位通过另外一个CH 2与另外一个azaphilone片段的C-5’位相连。
经分析确定所得化合物1的化学结构如下：
Figure PCTCN2021137672-appb-000002
实施例3：根系伸长抑制实验
取十字花科鼠耳芥属植物拟南芥的种子，用5％次氯酸钠溶液消毒，再用无菌水冲洗，擦干水分。将实施例1所得化合物1用二甲基亚砜(DMSO)制成终浓度40mg/mL的母液，备用；吸取母液加入至25mL的1/2MS培养基中，使化合物1浓度分别为8μg/mL、16μg/mL、32μg/mL，作为处理组。以加入20μL的DMSO作为空白对照组。每个平板上均匀加入5粒长势一致的种子，每组设3个平行实验。将各组平板放在恒温(23±1℃)的培养室中培养，光周期L/D为18h/6h。9天后观察各组根系生长情况。结果见图6。
结果显示：化合物1在浓度8～32μg/mL下对拟南芥种子根系伸长具有明显的抑制作用，其中浓度32μg/mL的平均抑制率达到90％以上。
以上所述仅为本发明的较佳实施例而已，但并不构成对本发明的限定，凡在本发明的精神和原则之内，所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。

Claims (10)

  1. 一种嗜氮酮类多聚体化合物，其特征在于，其结构式如以下式I所示：
    Figure PCTCN2021137672-appb-100001
  2. 权利要求1所述嗜氮酮类多聚体化合物的制备方法，其特征在于，包括以下步骤：
    (1)将真菌muyocopron laterale接种于培养基中发酵培养，得发酵产物，发酵产物用乙酸乙酯超声提取，减压浓缩至干，得总浸膏；
    (2)总浸膏用甲醇溶解，进行硅胶柱层析，洗脱系统为体积比100:0～1:1的二氯甲烷-甲醇溶液，经TLC检测合并，共得到7个馏分Fr.A～Fr.G；
    (3)馏分Fr.B经葡聚糖凝胶色谱柱分离，用甲醇等度洗脱，所得馏分通过半制备液相色谱仪进行分离，以甲醇-水为流动相，得权利要求1所述嗜氮酮类多聚体化合物。
  3. 根据权利要求2所述的制备方法，其特征在于，所述步骤(3)中，甲醇-水的体积比为70:30。
  4. 根据权利要求2所述的制备方法，其特征在于，半制备液相色谱的色谱柱型号为：YMC-Pack ODS-A。
  5. 根据权利要求2所述的制备方法，其特征在于，所述培养基由每60g大米加80mL水混合而成。
  6. 根据权利要求2所述的制备方法，其特征在于，所述馏分Fr.B为经体积比99:1的二氯甲烷-甲醇洗脱所得的馏分。
  7. 根据权利要求2所述的制备方法，其特征在于，发酵培养条件为：28℃静置培养30d。
  8. 根据权利要求2所述的制备方法，其特征在于，所述葡聚糖凝胶色谱柱型号为Sephadex LH-20。
  9. 权利要求1所述嗜氮酮类多聚体化合物在防治杂草中的应用。
  10. 权利要求1所述嗜氮酮类多聚体化合物在抑制植物根系生长方面的应用。
PCT/CN2021/137672 2021-08-18 2021-12-14 一种嗜氮酮类多聚体化合物及其制备方法和应用 WO2023019821A1 (zh)

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