CN117837600A - Application of Iheyamine A compound in preventing and treating agricultural pathogenic bacteria - Google Patents
Application of Iheyamine A compound in preventing and treating agricultural pathogenic bacteria Download PDFInfo
- Publication number
- CN117837600A CN117837600A CN202410002863.6A CN202410002863A CN117837600A CN 117837600 A CN117837600 A CN 117837600A CN 202410002863 A CN202410002863 A CN 202410002863A CN 117837600 A CN117837600 A CN 117837600A
- Authority
- CN
- China
- Prior art keywords
- iheyamine
- compound
- agricultural
- bacteria
- preventing
- 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
- KOOCXIZXRFRLJU-UHFFFAOYSA-N iheyamine A Natural products C12=CC(OC)=CC=C2N=C2C1=NC=CC1=C2NC2=CC=CC=C21 KOOCXIZXRFRLJU-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 244000052616 bacterial pathogen Species 0.000 title claims abstract description 13
- -1 Iheyamine A compound Chemical class 0.000 title claims abstract description 7
- 230000001580 bacterial effect Effects 0.000 claims abstract description 13
- 241000207199 Citrus Species 0.000 claims abstract description 5
- 235000007688 Lycopersicon esculentum Nutrition 0.000 claims abstract description 5
- 235000020971 citrus fruits Nutrition 0.000 claims abstract description 5
- 230000001717 pathogenic effect Effects 0.000 claims abstract description 5
- 240000003768 Solanum lycopersicum Species 0.000 claims abstract 2
- 241000894006 Bacteria Species 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 241000589615 Pseudomonas syringae Species 0.000 claims 1
- 241000589636 Xanthomonas campestris Species 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 7
- 241000589623 Pseudomonas syringae pv. syringae Species 0.000 abstract description 6
- 240000007594 Oryza sativa Species 0.000 abstract description 5
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 5
- 239000003899 bactericide agent Substances 0.000 abstract description 5
- 235000009566 rice Nutrition 0.000 abstract description 5
- 235000016639 Syzygium aromaticum Nutrition 0.000 abstract description 4
- 241000589649 Xanthomonas campestris pv. campestris Species 0.000 abstract description 4
- 241001272684 Xanthomonas campestris pv. oryzae Species 0.000 abstract description 2
- 244000061408 Eugenia caryophyllata Species 0.000 abstract 1
- 241000589655 Xanthomonas citri Species 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000001963 growth medium Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 229930013930 alkaloid Natural products 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229940079593 drug Drugs 0.000 description 4
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 4
- 238000009630 liquid culture Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 101001018064 Homo sapiens Lysosomal-trafficking regulator Proteins 0.000 description 3
- 241000227653 Lycopersicon Species 0.000 description 3
- 102100033472 Lysosomal-trafficking regulator Human genes 0.000 description 3
- 244000038561 Modiola caroliniana Species 0.000 description 3
- 235000010703 Modiola caroliniana Nutrition 0.000 description 3
- 244000223014 Syzygium aromaticum Species 0.000 description 3
- 150000003797 alkaloid derivatives Chemical class 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229930186591 iheyamine Natural products 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 244000000005 bacterial plant pathogen Species 0.000 description 2
- 235000015278 beef Nutrition 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000004308 thiabendazole Substances 0.000 description 2
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 2
- 229960004546 thiabendazole Drugs 0.000 description 2
- 235000010296 thiabendazole Nutrition 0.000 description 2
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 2
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000251557 Ascidiacea Species 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- 241000520892 Xanthomonas axonopodis Species 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Classifications
-
- 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
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention belongs to the field of natural pharmaceutical chemistry, and discloses a novel application of Iheyamine A compounds in preventing and treating agricultural diseases caused by agricultural pathogenic bacteria rice bacterial blight bacteria Xanthomonas oryzae pv.oryzae ACCC 11602, citrus canker Xanthomonas axonopodis pv.Citri, tomato bacterial wilt pseudoo-monas sollamacearum, xanthomonas campestris Xanthomonas campestris pv.campestris and Pseudomonas syringae clove pathogenic varieties Pseudomonas syringae pv.syringae. The Iheyamine A compound has the characteristics of novel structure and high efficiency as a novel agricultural bactericide, and has the value of further researching and developing the novel agricultural bactericide.
Description
Technical Field
The invention belongs to the field of natural pharmaceutical chemistry, and discloses application of an Iheyamine A compound in preventing and treating agricultural bacteria.
Background
The alkaloid has wide application value in the agricultural field, and one of the effects is used as a bactericide for preventing and controlling agricultural pathogenic bacteria. Alkaloids generally have a broad spectrum of antimicrobial activity and can interfere with the physiological metabolic processes of bacteria through different mechanisms, thereby effecting inhibition of the growth of pathogenic bacteria. Iheyamine a was a natural alkaloid with a bisindole structure isolated from the ascidian animal polycitraella sp. At present, less research on the efficacy of the alkaloids, especially on the aspect of antibiosis, is not reported yet. The invention discovers that the Iheyamine A compound has excellent inhibition effect on agricultural pathogenic bacteria for the first time, and accordingly, the Iheyamine A compound has important scientific value in resisting infection of plant pathogenic bacteria by researching the alkaloid and developing a bactericide with a brand new action target.
The Iheyamine A and the derivatives thereof have stronger antibacterial activity on agricultural pathogenic bacteria rice bacterial blight bacteria Xanthomonas oryzae pv.oryzae ACCC 11602, citrus canker bacteria Xanthomonas axonopodis pv.Citrus, tomato bacterial wilt Pseudo-monas sollamacearum, xanthomonas campestris Xanthomonas campestris pv.campestris, pseudomonas syringae clove pathogenic varieties Pseudomonas syringae pv.syringae and the like, and are expected to be further developed into novel agricultural bactericides.
Disclosure of Invention
The invention provides a new application of Iheyamine A and derivatives thereof in resisting agricultural pathogenic bacteria, which is used for preventing and treating agricultural bacterial diseases. Iheyamine A and derivatives thereof are shown in chemical formula 1.
The application of the invention protects the application of the Iheyamine A and the derivatives thereof in preparing medicaments for preventing and treating or resisting plant pathogenic bacteria such as rice bacterial blight bacteria, citrus canker bacteria, tomato bacterial wilt bacteria, xanthomonas campestris, pseudomonas syringae, clove pathogenic varieties and the like.
Detailed Description
The foregoing invention is further described in the following detailed description of the invention in order that the same may be better understood. But this should not be construed as limiting the invention. The experimental methods described in the following examples are conventional, unless otherwise specified.
Example 1: synthesis of Iheyamine a and derivatives thereof
The compounds of the present invention were synthesized as indicated above.
Various substituted isatins (1.0 mmol), anhydrous potassium carbonate (1.2 mmol), potassium iodide (0.2 mmol) and 10mL DMF were added to a 100mL round bottom flask. The mixture was cooled in an ice water bath and 4-methoxybenzyl chloride (1.1 mmol) was added dropwise. The reaction mixture was heated to 110 ℃ using an oil bath and stirred for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, poured into water and extracted with ethyl acetate. The organic layer was washed with water and the combined organic phases were washed with Na 2 SO 4 Dried and concentrated under reduced pressure to obtain a crude product, and intermediate 1 was purified by column chromatography.
To intermediate 1 (1.0 mmol), tryptamine (11.1 mmol) and EtOH (5 mL) acetic acid (5 mL) was slowly added at room temperature, then the mixture was heated to 40 ℃ using an oil bath and stirred for 15 hours. The mixture was concentrated under reduced pressure and diluted with ethyl acetate. The organic phase was saturated with NaHCO, respectively 3 The solution was washed with 1N HCl solution. The combined organic fractions were then washed with brine, and dried over Na 2 SO 4 Dried, filtered and concentrated under reduced pressure to give the crude product which is used directly in the next step.
The above product was dissolved in 10mL of acetonitrile, and 4-methylbenzenesulfonyl chloride (1.2 mmol) and K were added at room temperature 2 CO 3 (2.0 mmol) the mixture was heated to 80℃using an oil bath and stirredAnd (5) at night. The mixture was filtered, and the filtrate was concentrated to give a crude product, which was purified by column chromatography to give intermediate 2.
Intermediate 2 (0.34 mmol) was dissolved in 3mL dry toluene and Red-Al (0.37mmol,3.5N in toluene) was added slowly at 0deg.C using N 2 Protected and stirred at 0 ℃ for 5 hours. To the reaction mixture was added 5% aqueous naoh and ethyl acetate solution. The combined organic phases were washed with water, brine, and with Na 2 SO 4 The organic phase was dried, filtered and concentrated to afford intermediate 3.
To intermediate 3 above was added 10mL TFA, and the reaction mixture was then heated to 90 ℃ using an oil bath and stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure to remove TFA. Purifying by column chromatography to obtain the target product.
Iheyamine a; a mauve solid; yield 50%; 1 H NMR(400MHz,DMSO-d 6 )δ9.26(d,J＝6.4Hz,1H),9.19(s,1H),8.72(d,J＝8.0Hz,1H),8.02(dd,J＝8.1,2.9Hz,1H),7.98-7.91(m,2H),7.92(d,J＝5.7Hz,1H),7.65(t,J＝7.5Hz,1H),7.52(dt,J＝9.0,2.4Hz,1H),3.96(d,J＝2.0Hz,3H).ESI-MS calcd for C 19 H 13 N 3 O,[M+H + ],299.1059；found 300.1143.
compound 2; red solid; yield 52%; 1 H NMR(400MHz,DMSO-d 6 )δ9.28(d,J＝6.2Hz,1H),9.20(d,J＝6.0Hz,1H),8.71(d,J＝8.0Hz,1H),8.25-8.17(m,1H),8.03-7.95(m,2H),7.91(t,J＝7.6Hz,1H),7.74(dd,J＝10.4,7.8Hz,1H),7.65(t,J＝7.5Hz,1H).ESI-MS calcd for C 18 H 10 FN 3 ,[M+H + ],287.0859；found 288.0908.
compound 3; a mauve solid; yield 51%; 1 H NMR(400MHz,DMSO-d 6 )δ9.12(s,1H),9.01(d,J＝7.6Hz,1H),8.65(d,J＝7.7Hz,1H),8.43(t,J＝7.6Hz,1H),7.95(t,J＝7.5Hz,2H),7.88-7.80(m,1H),7.67-7.57(m,1H),7.57-7.48(m,1H).ESI-MS calcd for C 18 H 10 ClN 3 ,[M+H + ],303.0563；found 304.0614.
compound 4; a mauve solid; yield 50%; 1 H NMR(400MHz,DMSO-d 6 )δ9.04(d,J＝6.6Hz,1H),8.89(d,J＝6.7Hz,1H),8.59(d,J＝7.9Hz,1H),8.44(d,J＝7.8Hz,1H),7.94(d,J＝8.1Hz,1H),7.88(d,J＝8.0Hz,1H),7.78(dt,J＝11.9,7.6Hz,2H),7.57-7.49(m,2H).ESI-MS calcd for C 18 H 11 N 3 ,[M+H + ],269.0953；found 270.1025.
example 2: iheyamine A and determination of activity of derivative thereof against agricultural pathogenic bacteria
The strain used in this experiment was a laboratory-80℃strain frozen with 30% glycerol. The frozen strains were taken out, streaked on NB solid medium (beef extract: 3g, peptone: 5g, yeast powder: 1g, sucrose: 10g, agar: 15g, distilled water: 1L, pH7.0; sterilization at 121 ℃ C. For 20 min), and cultured at a constant temperature of 28 ℃ C. Until single colonies were grown, respectively. The single colony on the solid culture medium is respectively picked up to the agricultural bacteria NB liquid culture medium (beef extract: 3g, peptone: 5g, yeast powder: 1g, sucrose: 10g, distilled water: 1L; sterilization at 121 ℃ C. For 20 min), and shake culture is carried out at a constant temperature of 28 ℃ C., 180rpm to the logarithmic phase. Diluting the strain in logarithmic growth phase with corresponding liquid culture medium to about 10 6 CFU/mL was ready for use. The compounds are respectively dissolved by DMSO, added into a liquid culture medium, and evenly mixed to prepare a liquid culture medium containing liquid with the concentration of 200 mug/mL. Taking 50 mu L of the drug-containing culture medium and the same volume of the drug-containing culture medium containing about 10 6 CFU/mL bacterial cultures were added to wells of 96-well plates at a final dosing concentration of 100. Mu.g/mL. A control was made of 100. Mu.L of the same concentration of bacterial liquid containing an equivalent amount of DMSO. Culturing 96-well plate in 28 deg.C incubator for 24-48 hr until bacteria liquid of control group grows out, and measuring OD value (OD) 600 ). And the OD values of 100. Mu.L of the liquid medium and the reagent at a concentration of 100. Mu.g/mL were additionally measured, and the OD values caused by the medium and the reagent themselves were corrected. The calculation formula for the corrected OD value and the inhibition rate is as follows:
corrected OD = sterile medium OD-sterile culture OD;
inhibition ratio = (corrected control culture broth OD value-corrected drug-containing culture broth OD value)/corrected control culture broth OD value x 100%
Iheyamine A and its derivative liquid medium in 96 hole plate through double dilution method to obtain 50 u L of serial concentration liquid medium, and the inhibition rate corresponding to the serial concentration is determined according to the same test method.
All experiments were set up in triplicate.
The activity test is carried out on Iheyamine A and derivatives thereof and a positive control agent thiabendazole (the purity is 20 percent, the thiabendazole is purchased from Zhejiang Longwan chemical engineering Co., ltd.) aiming at pathogenic bacterial blight of paddy rice, bacterial canker, tomato bacterial wilt, xanthomonas campestris and clove pseudomonas syringae of common pathogenic bacteria in agriculture, the initial activity measurement concentration of Iheyamine A and derivatives thereof is 100 mug/mL, the initial activity measurement concentration of the positive control agent is 100 mug/mL, and the partial activity test data are shown in table 1.
TABLE 1 Activity of Iheyamine A and its derivatives against agricultural pathogenic bacteria
Note that: "-" indicates that the inhibition ratio of the compound to the strain is less than 90%, and the MIC value is the lowest drug concentration inhibiting the growth of 90% of bacteria, for which the relevant data is not calculated.
As can be seen from the biological measurement results in Table 1, the Iheyamine A derivative provided by the invention has excellent inhibition effect on the measurement strains, and the Iheyamine A derivative containing substituent groups has better antibacterial activity, wherein Iheyamine A and compound 2 have MIC on rice white leaf blight ACCC 11602 90 50 μg/mL and 12.5 μg/mL, respectively.
In conclusion, the Iheyamine A and the derivatives thereof have higher inhibition effect on agricultural pathogenic bacteria and have further research and development values.
Claims (3)
1. The invention relates to application of an Iheyamine A compound in preventing and treating agricultural pathogenic bacteria. The molecular structure characteristics of the compound are as follows:
wherein R is 1 、R 2 Can be a substituent group such as hydrogen, fluorine, chlorine, methoxy and the like.
2. The compound of claim 1, wherein the compound has the chemical formula:
3. use according to claims 1 to 2 of such compounds for controlling bacterial leaf blight, citrus canker, tomato bacterial wilt, xanthomonas campestris and 5 agropathogenic bacteria of the pseudomonas syringae pathogenic variety.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202410002863.6A CN117837600A (en) | 2024-01-02 | 2024-01-02 | Application of Iheyamine A compound in preventing and treating agricultural pathogenic bacteria |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202410002863.6A CN117837600A (en) | 2024-01-02 | 2024-01-02 | Application of Iheyamine A compound in preventing and treating agricultural pathogenic bacteria |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117837600A true CN117837600A (en) | 2024-04-09 |
Family
ID=90545037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202410002863.6A Pending CN117837600A (en) | 2024-01-02 | 2024-01-02 | Application of Iheyamine A compound in preventing and treating agricultural pathogenic bacteria |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN117837600A (en) |
-
2024
- 2024-01-02 CN CN202410002863.6A patent/CN117837600A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3007006C2 (en) | Quinolonecarboxylic acid derivatives, their salts, processes for their preparation and agents containing these derivatives | |
| NO160782B (en) | METHOD OF ANALOGUE FOR THE PREPARATION OF THERAPEUTIC ACTIVE 6,7-DIHYDRO-5,8-DIMETHYL-9-FLUOR-1-OXO-1H, 5H-BENZO- (IJ) -KINOLIZIN-2-CARBOXYLIC ACID. | |
| CN107674070A (en) | A kind of cyano group imines thiazolidine furoyl amine compound and its preparation method and application | |
| SU1600630A3 (en) | (benzofuran-2-yl)-imidazols displaying bactericidal and fungicidal activity | |
| CN117837600A (en) | Application of Iheyamine A compound in preventing and treating agricultural pathogenic bacteria | |
| NO143026B (en) | ANALOGY PROCEDURE FOR THE PREPARATION OF NEW, THERAPEUTICALLY EFFECTIVE HALOGEN DERIVATIVES | |
| CALVINO et al. | Chemical and biological studies on calvatic acid and its analogs | |
| CN115477584A (en) | Propiolic acid ester antibacterial agent and preparation method and application thereof | |
| RU2294330C1 (en) | 5-methyl-2-oxo-1-phenyl-4-ethoxycarbonyl-2,3-dihydro-1h-pyrrole-3-spiro-2-(3-benzoyl-4-hydroxy-1-ortho-hydroxyphenyl-5-oxo-2,5-dihydropyrroles) eliciting antimicrobial activity with respect to gram-positive microflora and method for their preparing | |
| CN117796407A (en) | Application of Tjiplazole D compound in preventing and treating agricultural pathogenic bacteria | |
| Raimondi et al. | Synthesis and anti‐staphylococcal activity of new halogenated pyrroles related to Pyrrolomycins F | |
| CN117958272A (en) | Application of Zephycandidine A compounds in prevention and treatment of agricultural pathogenic bacteria | |
| NO152840B (en) | PROCEDURE FOR THE PREPARATION OF DIBENZYLETERS | |
| CN111303092B (en) | 2, 4-dinitro-6-chloroaniline derivative, synthetic method and application thereof | |
| US3347874A (en) | 5-nitrofuryl-2-amidoximes | |
| CN106234385B (en) | A kind of application of 1,2,4- triazole derivatives of the structure containing benzopyrazines as fungicide | |
| CN114621214B (en) | Antibacterial Schiff base N-acylate, and preparation method and application thereof | |
| DE2163792C2 (en) | Process for the preparation of aminopenicillins | |
| CN112624962B (en) | Carbazolyl isopropanolamine derivatives with double chiral centers and preparation method and application thereof | |
| CN114621226B (en) | Matrine derivative and preparation method and application thereof | |
| CN114716451B (en) | Frutinone compound and preparation method and application thereof | |
| JPH10502377A (en) | Pyrid [3,2,1-i, j] [3,1] benzoxazine derivatives | |
| CN111018826B (en) | 2-cyano-5-oxo-ethyl valerate compound and application thereof | |
| RU2257386C1 (en) | 20-aroyl-12-hydroxy-17,17-dimethyl-3-phenyl-3,10,13- triazapentacyclo-[10.7.1.01,10.04,9.014,19]-e icosa-4,6,8,14(19)-tetraene-2,11,15-triones and method for their preparing | |
| CN114097804A (en) | Application of diaminopyrimidine compound in preventing and treating agricultural pathogenic bacteria |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication |