CN113615700A - Application of parthenolide derivative in prevention and treatment of bacterial blight of rice - Google Patents
Application of parthenolide derivative in prevention and treatment of bacterial blight of rice Download PDFInfo
- Publication number
- CN113615700A CN113615700A CN202010385467.8A CN202010385467A CN113615700A CN 113615700 A CN113615700 A CN 113615700A CN 202010385467 A CN202010385467 A CN 202010385467A CN 113615700 A CN113615700 A CN 113615700A
- Authority
- CN
- China
- Prior art keywords
- rice
- parthenolide
- acid
- application
- bacterial blight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000004175 parthenolide derivatives Chemical class 0.000 title claims abstract description 37
- 241001272684 Xanthomonas campestris pv. oryzae Species 0.000 title claims abstract description 6
- 230000002265 prevention Effects 0.000 title claims abstract description 4
- 241000209094 Oryza Species 0.000 claims abstract description 19
- 235000007164 Oryza sativa Nutrition 0.000 claims abstract description 17
- 235000009566 rice Nutrition 0.000 claims abstract description 17
- 230000001580 bacterial effect Effects 0.000 claims abstract description 13
- 150000001875 compounds Chemical group 0.000 claims abstract description 8
- 239000000575 pesticide Substances 0.000 claims description 17
- -1 inorganic acid salts Chemical class 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
- 229960004889 salicylic acid Drugs 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 abstract description 7
- 241000196324 Embryophyta Species 0.000 abstract description 4
- 201000010099 disease Diseases 0.000 abstract description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
- BUQLXKSONWUQAC-UHFFFAOYSA-N Parthenolide Natural products CC1C2OC(=O)C(=C)C2CCC(=C/CCC1(C)O)C BUQLXKSONWUQAC-UHFFFAOYSA-N 0.000 description 13
- 229940069510 parthenolide Drugs 0.000 description 13
- KTEXNACQROZXEV-PVLRGYAZSA-N parthenolide Chemical compound C1CC(/C)=C/CC[C@@]2(C)O[C@@H]2[C@H]2OC(=O)C(=C)[C@@H]21 KTEXNACQROZXEV-PVLRGYAZSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 244000052769 pathogen Species 0.000 description 9
- 230000001717 pathogenic effect Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 230000003385 bacteriostatic effect Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 230000003902 lesion Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241000208838 Asteraceae Species 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
- 244000035851 Chrysanthemum leucanthemum Species 0.000 description 2
- 235000008495 Chrysanthemum leucanthemum Nutrition 0.000 description 2
- 206010027146 Melanoderma Diseases 0.000 description 2
- HATRDXDCPOXQJX-UHFFFAOYSA-N Thapsigargin Natural products CCCCCCCC(=O)OC1C(OC(O)C(=C/C)C)C(=C2C3OC(=O)C(C)(O)C3(O)C(CC(C)(OC(=O)C)C12)OC(=O)CCC)C HATRDXDCPOXQJX-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000010413 mother solution Substances 0.000 description 2
- 231100000956 nontoxicity Toxicity 0.000 description 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
- 229930009674 sesquiterpene lactone Natural products 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- PIOKGAUSPFWRMD-UHFFFAOYSA-N 4-(trifluoromethoxy)benzene-1,2-diamine Chemical compound NC1=CC=C(OC(F)(F)F)C=C1N PIOKGAUSPFWRMD-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 235000000604 Chrysanthemum parthenium Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241000223221 Fusarium oxysporum Species 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- 241000218378 Magnolia Species 0.000 description 1
- 240000003293 Magnolia grandiflora Species 0.000 description 1
- 235000008512 Magnolia grandiflora Nutrition 0.000 description 1
- 241000218377 Magnoliaceae Species 0.000 description 1
- 241000233654 Oomycetes Species 0.000 description 1
- AVFIYMSJDDGDBQ-UHFFFAOYSA-N Parthenium Chemical compound C1C=C(CCC(C)=O)C(C)CC2OC(=O)C(=C)C21 AVFIYMSJDDGDBQ-UHFFFAOYSA-N 0.000 description 1
- 241001495454 Parthenium Species 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- 241000233616 Phytophthora capsici Species 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 244000203593 Piper nigrum Species 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 241000723873 Tobacco mosaic virus Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000008384 feverfew Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 244000000004 fungal plant pathogen Species 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 125000000686 lactone group Chemical group 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000000810 parthenolide group Chemical group 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000002107 sesquiterpene lactone derivatives Chemical class 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N tert-butyl alcohol Substances CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明公开了一种小白菊内酯衍生物在防治水稻白叶枯病方面的应用，其化合物结构如下图（Ⅰ）所示。该小白菊内酯衍生物对水稻白叶枯病菌有很好的抑制作用，在植物病害的防治中具有较好的应用前景。
The invention discloses the application of a parthenolide derivative in preventing and treating bacterial blight of rice, and its compound structure is shown in the following figure (I). The parthenolide derivative has a good inhibitory effect on rice bacterial blight, and has a good application prospect in the prevention and control of plant diseases.
Description
Technical Field
The invention belongs to the technical field of pesticides, and particularly relates to an application of a parthenolide derivative in preventing and treating bacterial blight of rice.
Background
At present, more than 80% of pesticides used in China are chemical pesticides, the use of the chemical pesticides greatly promotes the development of modern agriculture, but with the remarkable improvement of the grain yield, people pay more and more attention to the grain safety problem and the environmental problem brought by the use of the chemical pesticides, so that the research of the field of pollution-free plant source pesticide industry and biological control obtains an inexhaustible development opportunity. The botanical pesticide mainly refers to a pesticide prepared from natural active substances extracted from plant resources, and generally refers to a pesticide artificially synthesized according to natural substances or similar derivative structures thereof. The pesticide can be naturally degraded in nature, and has the advantages of environmental friendliness, high efficiency, unique action mode of natural active ingredients, difficult generation of drug resistance, safety and no toxicity to non-target organisms and the like. Is an ideal pesticide for developing organic agriculture and promoting sustainable development of agriculture.
The parthenolide is the commonly used herb medicine, parthenolide [ Feverfew ], [ solution of ChrysanthemumTanacetum parthenium (L.) Sch. Bip.]One of the main active ingredients of (1) can be usually obtained by separating and extracting from the plants of the family Compositae (Asteraceae) or Magnoliaceae (Magnolia), and the source is very wide; it is a sesquiterpene lactone compound, mainly composed of three isoprene units and one lactone group (Ghantous)et al., 2013). Parthenolide exhibits inhibitory activity against a variety of plant pathogenic fungi, oomycetes, bacteria and the like. Research shows that the parthenolide can relieve symptoms caused by phytophthora capsici on pepper leaves at concentrations of 250 mu g/mL and 200 mu g/mL respectively, and has good inhibitory activity on tobacco mosaic virus; the sesquiterpene lactone mixture extracted from the southern magnolia leaves has an inhibition effect on apple rot pathogen and cabbage black spot pathogen, and the inhibition rate reaches 81.4% and 52.1% when the concentration is 1.0 mg/mL; at a concentration ofWhen the concentration is 5.0 mg/mL, the bacteriostasis rate to wheat scab pathogen, cotton fusarium wilt pathogen and apple ring rot pathogen is more than 50.0 percent; after the parthenolide is obtained by purification, the compound is found to have good inhibitory activity on apple canker, cabbage black spot pathogen, apple ring rot pathogen and rice leaf blight pathogen, and the EC of the compound is50The values were 4.96. + -. 0.16. mu.g/mL, 1.99. + -. 0.19. mu.g/mL and 4.87. + -. 0.21. mu.g/mL and 2.97. + -. 0.58. mu.g/mL, respectively. Parthenolide has the possibility of developing into novel botanical pesticides.
In the research of developing parthenolide pesticides, it is found that parthenolide activity is still not outstanding enough and water solubility is poor, so that certain structural modification is required to improve water solubility.
Disclosure of Invention
The invention aims to provide a preparation method of a parthenolide derivative and an application example of the parthenolide derivative in preventing and treating rice bacterial blight.
The parthenolide derivative related in the invention is a compound with a structure shown as a figure 1, and is hereinafter referred to as a parthenolide derivative (I):
FIG. 1 parthenolide derivative (I)
In the content of the invention, the parthenolide derivative (I) has very good activity against rice bacterial blight.
In the content of the invention, the parthenolide derivative (I) and the inorganic salt and the organic salt thereof have very good activity against rice bacterial blight. The pesticide prepared from the parthenolide derivative (I) contains a pesticide adjuvant composition, and has the activity of resisting phytopathogen.
The activity of the rice bacterial blight-resistant bacteria is measured by a hypha growth rate method.
The invention has the beneficial effects that: the parthenolide derivative (I) is used as an antibacterial agent and can effectively inhibit rice bacterial blight germ, and the parthenolide derivative (I) in the invention can be used for inhibiting rice whiteThe fusarium oxysporum has excellent inhibiting effect. The parthenolide derivative (I) has a novel structure and possibly has a novel action mechanism. The parthenolide derivative has no toxicity to human cells and can be used for farmland crops in a large range by the determination of an anti-tumor experiment. Parthenolide derivative EC in the invention500.52. + -. 0.18. mu.g/mL, compared to parthenolide EC502.97 +/-0.58 mu g/mL, and the activity is obviously improved. The water solubility of the parthenolide lactone can be greatly improved by acidifying the parthenolide lactone.
Detailed description of the invention
The present invention will be described in further detail with reference to examples and data, but the embodiments of the present invention are not limited thereto.
Example 1: the synthesis of parthenolide derivative (I), the compound represented in FIG. 1, is as follows:
parthenolide (PTL) is reacted with selenium dioxide and t-butanol peroxide (dodecane, about 5.5M) in methylene chloride as a solvent (4 a molecular sieve dried) to give the product MMB; performing a light extension reaction on MMB and Fmoc-12-aminododecanoic acid to obtain an ester, and removing an Fmoc protecting group by tetrabutylammonium fluoride to obtain a parthenolide derivative, namely the compound shown in the figure (I). White solid, 61 mg, yield 60.2%, (HRMS) (ESI) C27H44NO5 [M+H]+Theoretical value 462.3214, actual value 462.3359, FT-IR (KBr cm)-1): 3434 (υ NH), 2921 (υ C-H, CH2), 2851 (υ C-H, CH3), 1767 (υ C=O, CH2=C-C=O), 1728 (υ C=O, CH2-C=O-O), 1647 (υ C=C, CH-C=CH2), 1463 (υ C=C, CH2-C=CH), 1052 (υ C-O, C=O-O-CH), 1027 (υ C-O, C-O-CH), 1004 (υ C-O, O=C-O), 823 (δ C-N, N-C=O), 761 (δ C-H, CH) ; 1H NMR (300 MHz, DMSO-d 6): δ 5.75 (s, 1H, H-13b), 5.53 (s, 1H, H-13a), 5.31-5.34 (t, J = 4.89 Hz, 1H, H-1), 4.39-4.61 (q, J = 13.41 Hz, 2H, H-14), 3.99-4.06 (t, J = 9.30 Hz, 1H, H-6), 2.84 (s, 1H, H-5), 2.78 (d, J = 5.58 Hz, 2H, H-27), 2.66 (d, J = 8.19 Hz, 1H, H-7), 2.45 (d, J = 6.75 Hz, 2H, H-17), 2.29 (m, 4H, H-2,9), 2.02 (d, J = 7.35 Hz, 2H, H-18), 1.47 (m, 4H, H-3,8), 1.24 (m, 21H, NH2,H-15,19,20,21,22,23,24,25,26); 13C NMR (75 MHz, DMSO-d 6): δ 180.08, 175.74, 138.64, 132.68, 131.06, 127.25, 83.46, 68.89, 68.19, 62.72, 48.92, 42.90, 42.62, 36.54, 34.19, 32.90, 32.12, 32.05, 32.00, 31.89, 31.60, 29.86, 29.60, 28.64, 27.56, 26.16, 20.48.
Example 2: preparation of parthenolide derivative (I) hydrochloride
Dissolving 10mg of parthenolide derivative (I) in 4mL of diethyl ether, slowly adding concentrated hydrochloric acid diethyl ether solution (1M) into the diethyl ether solution until the solution is filled with hydrochloric acid steam, additionally adding 6mL of diethyl ether solvent, stirring to clarify the solution, placing the clarified solution in a refrigerator at 0 ℃ for 24h, separating out white crystals, and filtering to obtain 2.4mg of parthenolide derivative (I) hydrochloride with the yield of 23%.
Example 3: determination of bacteriostatic activity of parthenolide derivative (I) on rice bacterial leaf blight germ
The rice variety IR24 was grown in a greenhouse by a conventional method. Dissolving the parthenolide derivative (I) in DMSO to prepare a mother solution of 10000 mu g/mL, and diluting the mother solution by using DMSO in a double ratio to prepare a series of concentration gradients. Diluting the medicinal liquid with clear water to final concentration of 0, 25, 50, 100, 200 μ g/mL, and adding 0.1% Tween 20. The liquid medicine with the same volume and each concentration is evenly sprayed on the rice plants in the full tillering stage. The rice bacterial leaf blight is shaken to the logarithmic growth phase, and the turbidity is adjusted to OD600 = 1.0, using leaf-cutting inoculation method to inoculate pathogen onto rice leaf. The protective effect is tested inThe liquid medicine is inoculated with pathogenic bacteria 24 hours after being sprayed, and the treatment effect test is carried out 24 hours before the liquid medicine is sprayed. The test sets clear water contrast, and after the clear water contrast is full of diseases, the length of each treated lesion is investigated, and the control effect is calculated.
Control effect (%) = (length of solvent control lesion-length of drug-treated lesion)/length of solvent control lesion × 100.
Three pots of repetition are set for each treatment in the test, four rice plants are planted in each pot, and the test is repeated three times.
The test result shows that: the parthenolide derivative (I) has a strong inhibiting effect on rice bacterial blight. EC (EC)500.52. + -. 0.18. mu.g/mL.
Example 4: determination of bacteriostatic activity of parthenolide derivative (I) hydrochloride on rice bacterial blight germ
Only the parthenolide derivative was replaced with the parthenolide derivative hydrochloride salt in accordance with the bacteriostatic activity assay described in example 3. Tests show that the parthenolide derivative hydrochloride EC500.49. + -. 0.16. mu.g/mL.
Example 5: preparation of parthenolide derivative (I) bactericide
Placing 0.5 kg of surfactant (such as polyoxyethylene nonionic surfactant: OP-10) and parthenolide derivative in a homogenizer, heating to 50 deg.C, adding 1 kg of water into the homogenizer while stirring, stirring for 30 min, mixing well, cooling to room temperature to form water emulsion, and obtaining parthenolide derivative bactericide.
Description of the drawings:
FIG. 1 is a structural diagram of parthenolide derivative (I).
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010385467.8A CN113615700A (en) | 2020-05-09 | 2020-05-09 | Application of parthenolide derivative in prevention and treatment of bacterial blight of rice |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010385467.8A CN113615700A (en) | 2020-05-09 | 2020-05-09 | Application of parthenolide derivative in prevention and treatment of bacterial blight of rice |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113615700A true CN113615700A (en) | 2021-11-09 |
Family
ID=78376401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010385467.8A Pending CN113615700A (en) | 2020-05-09 | 2020-05-09 | Application of parthenolide derivative in prevention and treatment of bacterial blight of rice |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113615700A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114470195A (en) * | 2022-01-19 | 2022-05-13 | 同济大学 | Antifungal preparation, inhibitor for inhibiting expression of cell PD-L1 and application |
| CN114847297A (en) * | 2022-03-28 | 2022-08-05 | 郑州福道生态农业科技有限公司 | Pesticide composition for preventing and treating rice diseases |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120122943A1 (en) * | 2010-10-22 | 2012-05-17 | University Of Kentucky Research Foundation | Melampomagnolide B Derivatives as Antileukemic and Cytotoxic Agents |
| CN105815326A (en) * | 2016-03-11 | 2016-08-03 | 江苏省中国科学院植物研究所 | Preparation method and use of agricultural bactericide containing parthenolide |
| CN106366088A (en) * | 2015-07-24 | 2017-02-01 | 天津尚德药缘科技股份有限公司 | Parthenolide derivative, and medicinal composition, preparation method and use thereof |
| CN107793424A (en) * | 2016-08-31 | 2018-03-13 | 天津尚德药缘科技股份有限公司 | Parthenolide derivative, its medical composition and its use |
-
2020
- 2020-05-09 CN CN202010385467.8A patent/CN113615700A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120122943A1 (en) * | 2010-10-22 | 2012-05-17 | University Of Kentucky Research Foundation | Melampomagnolide B Derivatives as Antileukemic and Cytotoxic Agents |
| CN106366088A (en) * | 2015-07-24 | 2017-02-01 | 天津尚德药缘科技股份有限公司 | Parthenolide derivative, and medicinal composition, preparation method and use thereof |
| CN105815326A (en) * | 2016-03-11 | 2016-08-03 | 江苏省中国科学院植物研究所 | Preparation method and use of agricultural bactericide containing parthenolide |
| CN107793424A (en) * | 2016-08-31 | 2018-03-13 | 天津尚德药缘科技股份有限公司 | Parthenolide derivative, its medical composition and its use |
Non-Patent Citations (1)
| Title |
|---|
| 曹妍 等: "生物素化小白菊内酯的合成及其在互作蛋白筛选中的应用", 《中国化学会第十二届全国天然有机化学学术会议论文摘要集 工程科技I》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114470195A (en) * | 2022-01-19 | 2022-05-13 | 同济大学 | Antifungal preparation, inhibitor for inhibiting expression of cell PD-L1 and application |
| CN114847297A (en) * | 2022-03-28 | 2022-08-05 | 郑州福道生态农业科技有限公司 | Pesticide composition for preventing and treating rice diseases |
| CN116616302A (en) * | 2022-03-28 | 2023-08-22 | 郑州福道生态农业科技有限公司 | A fungicide active against field diseases |
| CN116671520A (en) * | 2022-03-28 | 2023-09-01 | 郑州福道生态农业科技有限公司 | Low-residue environment-friendly bactericide for resisting field diseases |
| CN114847297B (en) * | 2022-03-28 | 2024-03-29 | 郑州福道生态农业科技有限公司 | Pesticide composition for preventing and treating rice diseases |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103214532B (en) | Avermectin B2a/2bAmido derivative, derivative salt and avermectin B2a/2bThe Preparation method and use of amido derivative salt | |
| KR860001001B1 (en) | Process for the preparation of majusculamide c | |
| CN113615700A (en) | Application of parthenolide derivative in prevention and treatment of bacterial blight of rice | |
| CN109844095B (en) | Aspergillus niger F22 strain having nematicidal activity against plant parasitic nematodes and use thereof | |
| CN110818708B (en) | Compound containing fused heterocyclic structure, preparation method and application thereof, and bactericide | |
| CN113367133A (en) | Application of cinnamic acid and its derivatives as antibacterial agent for inhibiting plant pathogenic bacteria | |
| CN108450462B (en) | Synergistic application of farnesol to methoxyacrylic fungicides in the control of smut | |
| CN111616150B (en) | Pesticide composition containing sodium alginate oligosaccharide and vanilla thioketal and application thereof | |
| CN105815326B (en) | Preparation method and application of agricultural bactericide containing parthenolide | |
| KR101103345B1 (en) | Composition for controlling microalgae containing sesquiterpene compound | |
| CN1883267A (en) | Agricultural bactericide containing camptothecin or camptothecin derivative and application thereof | |
| Kumar | Adaptation of a blue-green alga to sodium selenate and chloramphenicol | |
| EP3040338B1 (en) | Novel microbial product having antifungal activity | |
| US20220242800A1 (en) | Composition and method for improving plant growth | |
| CN108271786B (en) | New application of ocotillol type compound as agricultural bactericide | |
| CN114027300B (en) | Application of isoeugenol and its methylated metabolites in inhibiting Phytophthora infestans and controlling plant diseases | |
| CN114766517A (en) | Application of vitex rotundifolia extract, pesticide and preparation method of pesticide | |
| CN114766499A (en) | Novel application of scopolamine and combination of scopolamine and chemical pesticide in prevention and treatment of plant late blight diseases | |
| CN113142204A (en) | Application of honokiol in preparation of bactericide for preventing and treating plant diseases caused by downy mildew | |
| CN113243380A (en) | Sterilization composition containing isotianil and Xinjunan acetate | |
| CN113350327A (en) | Application of cinnamic acid and its derivatives as antibacterial agent for inhibiting human pathogenic bacteria | |
| CN109984140B (en) | Microemulsion containing ethylicin and hymexazol | |
| CN104351179A (en) | Agricultural bacteriostatic activity of 8-phenyl (isopropyl) cumarin | |
| CN1520727A (en) | Mixed formulations for root-knot nematode control | |
| CN1074250C (en) | Application of diniconazole emulsion in preventing and treating sigatoka |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20211109 |
|
| WD01 | Invention patent application deemed withdrawn after publication |