Fibrauridine derivatives containing acylhydrazone structure, preparation method and application thereof

Abstract

This invention relates to the field of agricultural technology, and more particularly to cypermethrin derivatives containing an acylhydrazone structure, their preparation methods, and applications. Cypermethrin derivatives containing an acylhydrazone structure include those with the structural formula shown in formula (I): wherein, R... 1 Including at least one of alkyl, phenyl, furanyl, pyridyl, indoleyl and cycloalkyl, R 2 Including at least one of hydrogen, methyl, and ethyl; or, R 1 and R 2 The combined derivatives of white vine alkaloids containing acylhydrazone structures exhibit good activity in preventing and controlling plant viruses and in killing bacteria.

Description

TECHNICAL FIELD

[0001] The present application relates to the field of agricultural technology, and particularly relates to a Cryptolepine derivative containing an acylhydrazone structure and a preparation method and application thereof. BACKGROUND

[0002] In 1951, Gellert first isolated Cryptolepine with an indole quinoline structure from blood Cryptolepis sanguinolenta. The synthesis of Cryptolepine is earlier than extraction from nature. At present, the research on Cryptolepine and its derivatives is focused on the biological field, and the research on the application of Cryptolepine derivatives in agriculture is rare. SUMMARY

[0003] The present application aims to at least solve one of the technical problems in the related art. To this end, the present application provides a Cryptolepine derivative containing an acylhydrazone structure, which has good plant virus control and bactericidal activity.

[0004] In one aspect of the present application, the present application provides a Cryptolepine derivative containing an acylhydrazone structure, which includes a structural formula as shown in formula (I):

[0005]

[0006] wherein R 1 at least one of alkyl, phenyl, furanyl, pyridyl, indolyl and cycloalkyl, R 2 at least one of hydrogen, methyl and ethyl;

[0007] or R 1 and R 2 are combined into

[0008] Further, the alkyl includes at least one of ethyl, isobutyl and cyclopropyl.

[0009] Further, the phenyl is substituted by a substituent, and the substituent includes at least one of methyl, methoxy, Cl, Br and dimethylamine.

[0010] Further, the Cryptolepine derivative containing an acylhydrazone structure includes at least one of structural formulas as shown in formula (I-1) to formula (I-16):

[0011]

[0012] In another aspect of the present application, the present application provides a preparation method of the quebrachidine derivative containing an acylhydrazone structure as described above, and the preparation method comprises the following steps:

[0013] reacting to obtain the quebrachidine derivative containing an acylhydrazone structure;

[0014] wherein R 1 at least one of alkyl, phenyl, furanyl, pyridyl, indolyl and cycloalkyl, R 2 at least one of hydrogen, methyl and ethyl;

[0015] or R 1 and R 2 are combined into

[0016] Further, the preparation method comprises the following steps:

[0017] dissolving in ethanol, adding 1% to 3% of molar equivalent of concentrated HCl, heating and refluxing at 70 to 90℃ for 5 to 7h, and after the reaction is completed, sequentially performing cooling, washing and drying to obtain the quebrachidine derivative containing an acylhydrazone structure.

[0018] Further, the molar ratio of (4 to 6):(5 to 7).

[0019] Further, the washing comprises: washing the solid product obtained after cooling with ethanol and diethyl ether for four to five times.

[0020] In another aspect of the present application, the present application provides an application of the quebrachidine derivative containing an acylhydrazone structure as described above in treating plant viral diseases.

[0021] In another aspect of the present application, the present application provides an application of the quebrachidine derivative containing an acylhydrazone structure as described above in resisting bacteria.

[0022] The one or more technical solutions in the embodiments of the present application have at least one of the following technical effects:

[0023] ​The acylhydrazone structure and the quebrachine main body structure in the acylhydrazone structure-containing quebrachine derivative of the present application have a synergistic effect, the hydrogen bond acceptor and the hydrogen bond donor in the acylhydrazone structure can increase more hydrogen bond interaction between the quebrachine derivative and the target protein relative to the quebrachine main body structure, thereby improving the biological activity of the molecule, and meanwhile, the introduction of the acylhydrazone structure can improve the physical and chemical properties of the molecule, so that the acylhydrazone structure-containing quebrachine derivative of the present application has good anti-plant virus activity and bactericidal activity, especially good anti-tobacco mosaic virus activity and good bactericidal activity against the pathogenic bacteria causing rice sheath blight.

[0024] Additional aspects and advantages of the present application will be made apparent from the following description. DETAILED DESCRIPTION

[0025] In order to make the objects, technical solutions and advantages of the present application clearer, the technical solutions in the present application are described below clearly and completely. Obviously, the described embodiments are only some of the embodiments of the present application, rather than all the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative efforts belong to the scope of protection of the present application. The following embodiments are used to illustrate the present application, but cannot be used to limit the scope of the present application.

[0026] In the description of the embodiments of the present application, it should be noted that the orientations or positional relationships indicated by the terms "center", "longitudinal", "lateral", "upper", "lower", "front", "back", "left", "right", "vertical", "horizontal", "top", "bottom", "inner", "outer" and the like are only for facilitating the description of the embodiments of the present application and simplifying the description, and are not intended to indicate or imply that the device or element referred to must have a particular orientation, be constructed and operated in a particular orientation, and therefore cannot be understood as a limitation on the embodiments of the present application. In addition, the terms "first", "second", "third" are only for description purposes, and cannot be understood as indicating or implying relative importance.

[0027] In the description of the embodiments of the present application, it should be noted that, unless otherwise explicitly specified and limited, the terms "connected", "connected" should be understood broadly, for example, can be fixedly connected, can be detachably connected, or integrally connected; can be mechanically connected, or electrically connected; can be directly connected, or indirectly connected through an intermediate medium. For those skilled in the art, the specific meanings of the above terms in the embodiments of the present application can be understood according to the specific circumstances.

[0028] In the embodiments of the present application, unless otherwise explicitly specified and limited, the first feature is "on" or "under" the second feature, which can be that the first and second features are in direct contact, or the first and second features are in indirect contact through an intermediate medium. Moreover, the first feature can be "above", "over" and "on" the second feature, which can be that the first feature is directly above or obliquely above the second feature, or only means that the horizontal height of the first feature is higher than that of the second feature. The first feature can be "under", "below" and "underneath" the second feature, which can be that the first feature is directly below or obliquely below the second feature, or only means that the horizontal height of the first feature is less than that of the second feature.

[0029] In the description of the present application, the description of the terms "one embodiment", "some embodiments", "an example", "a specific example" or "some examples" and the like means that the specific features, structures, materials or characteristics described in connection with the embodiment or example are included in at least one embodiment or example of the embodiments of the present application. In the present description, the illustrative description of the above terms does not necessarily refer to the same embodiment or example. Moreover, the specific features, structures, materials or characteristics described can be combined in any appropriate manner in any one or more embodiments or examples. In addition, the skilled person in the art can combine and combine the different embodiments or examples described in the present description and the features of the different embodiments or examples without contradiction.

[0030] In one aspect of the present application, the present application provides an acylhydrazone structure-containing quebrachine derivative, which comprises a structural formula as shown in formula (I):

[0031]

[0032] wherein R 1 comprises at least one of alkyl, phenyl, furanyl, pyridyl, indolyl and cycloalkyl, R 2 comprises at least one of hydrogen, methyl and ethyl;

[0033] or R 1 and R 2 are combined into

[0034] In the acylhydrazone structure-containing quebrachine derivative of the present application, there is a synergistic effect between the acylhydrazone structure and the quebrachine main structure, the hydrogen bond acceptor and the hydrogen bond donor in the acylhydrazone structure can increase more hydrogen bond interactions between the quebrachine derivative and the target protein relative to the quebrachine main structure, thereby improving the biological activity of the molecule. At the same time, the introduction of the acylhydrazone structure can improve the physicochemical properties of the molecule, so that the acylhydrazone structure-containing quebrachine derivative of the present application has good anti-plant virus activity and bactericidal activity, especially good anti-tobacco mosaic virus activity and good bactericidal activity against the pathogenic bacteria causing rice sheath blight.

[0035] In some embodiments of the present application, the alkyl group comprises at least one of ethyl, isobutyl and cyclopropyl.

[0036] In some embodiments of the present application, the phenyl group is substituted by a substituent group comprising at least one of methyl, methoxy, Cl, Br and dimethylamino.

[0037] In some embodiments of the present application, the quebrachine derivative comprising an acylhydrazone structure comprises at least one of the structural formulae as shown in formula (I-1) to formula (I-16):

[0038]

[0039] In another aspect of the present application, the present application provides a preparation method of the quebrachine derivative comprising an acylhydrazone structure as described above, which comprises the following steps:

[0040] reacting to obtain the quebrachine derivative comprising an acylhydrazone structure;

[0041] wherein R 1 comprises at least one of alkyl, phenyl, furanyl, pyridyl, indolyl and cycloalkyl, R 2 comprises at least one of hydrogen, methyl and ethyl;

[0042] or, R 1 and R 2 are combined into

[0043] In some embodiments of the present application, the preparation method comprises the following steps:

[0044] dissolving in ethanol, adding 1% to 3% molar equivalent of concentrated HCl, heating to reflux at 70 to 90 ℃ (for example, it can be 70 ℃, 80 ℃ or 90 ℃, etc.) for 5 to 7 h (for example, it can be 5 h, 6 h or 7 h, etc.), and after the reaction is completed, sequentially performing cooling, washing and drying to obtain the quebrachine derivative comprising an acylhydrazone structure.

[0045] It should be noted that the concentrated HCl herein refers to an aqueous hydrochloric acid solution with a mass fraction of 36% to 38%.

[0046] In the preparation of the quebrachine derivative comprising an acylhydrazone structure of the present application, the inventors have unexpectedly found that the use of the amount of concentrated HCl as a catalyst in the present application can significantly improve the efficiency and yield of the acylhydrazone reaction.

[0047] ​In some embodiments of the present invention The molar ratio is (4-6):(5-7), for example, it can be 4:5, 4:6, 4:7, 5:5, 5:6, 5:7, 6:5, 6:6 or 6:7, etc.

[0048] In some embodiments of the present invention, the washing includes washing the solid product obtained after cooling with ethanol and ether four to five times.

[0049] In some specific embodiments of the present invention, the preparation method of the leucocephaline derivative containing an acylhydrazone structure includes the following steps: ... (166.0 mg, 0.6 mmol) and (1.2 equivalents, 0.72 mmol) dissolved in ethanol (15 mL), then concentrated HCl was added. (1% equivalent), heated under reflux at 80°C for 6 hours. After the reaction was complete, cooled to room temperature, the precipitate was collected by filtration, washed four to five times with ethanol and diethyl ether, and dried to obtain the leucovorin derivative containing an acylhydrazone structure. The specific reaction procedure is as follows:

[0050]

[0051] Among them, R 1 R 2 As described above, I will not go into further detail here.

[0052] In another aspect of the invention, the invention provides the application of the acetohydrazone-containing derivative of leucocytoside as described above in the treatment of plant viral diseases.

[0053] In some embodiments of the present invention, the baicalein derivative containing a hydrazone structure exhibits good anti-tobacco mosaic virus activity.

[0054] In another aspect of the invention, the invention provides the application of the acetohydrazone-containing derivative of leucocytokinin as described above in antibacterial applications.

[0055] In some embodiments of the present invention, the hydrazone-containing cypermethrin derivatives exhibit good bactericidal activity against pathogens that cause rice sheath blight.

[0056] The present invention will be further described below with reference to specific embodiments. It should be noted that the following embodiments are only used to explain the present invention and should not be construed as limiting the present invention.

[0057] Example

[0058] Example 1

[0059] The preparation method of the acetylhydrazone-containing leucocele alkaloid derivative (structure shown in formula (I-1)) includes the following steps:

[0060] 1. Dissolve N,O-1,3-diacetylindole (5.00 g, 23.0 mmol) in 50 mL of water and stir under argon protection. Slowly add 50 mL of aqueous solution of indigo (3.40 g, 23.0 mmol) and 50 mL of aqueous solution of KOH (26.00 g). Stir at room temperature for 6 days, and monitor the reaction using a TCL (thin-layer chromatography plate). After the reaction is complete, add 20 mL of water, heat at 70 °C for 20 min, filter, wash with water at 60 °C, add an equal volume of ethanol to the filtrate, and reduce the pH to 1 with concentrated HCl. Wash the product with ethanol and water (ethanol to water volume ratio 1:1), and dry to obtain 10H-indolo[3,2-b]quinoline-11-carboxylic acid.

[0061] 2. 10H-indolo[3,2-b]quinoline-11-carboxylic acid (1.31 g, 5.0 mmol) was dissolved in DMF (N,N-dimethylformamide, 40 mL), DMAP (4-dimethylaminopyridine, 916.0 mg, 7.5 mmol) and CH3OH (243.0 μL, 6.0 mmol) were added and stirred for 20 min. DCC (dicyclohexylcarbodiimide, 1.54 g, 7.5 mmol) was added and stirred overnight at room temperature. After the reaction was completed, a large amount of water was added, and the mixture was extracted three times with ethyl acetate. The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and then distilled under reduced pressure. The purified product was obtained by column chromatography to give methyl 10H-indolo[3,2-b]quinoline-11-carboxylic acid.

[0062] 3. Methyl 10H-indo[3,2-b]quinoline-11-carboxylic acid (1.30 g, 4.7 mmol) was dissolved in ethanol (30 mL), heated to dissolve, and then hydrazine hydrate (7.5 mL) was added. The mixture was then heated to reflux at 80 °C for 2 h. After the reaction was complete, the mixture was cooled to room temperature to precipitate a yellow precipitate. The precipitate was filtered, washed three times with 50% cold ethanol aqueous solution, and dried to obtain 10H-indo[3,2-b]quinoline-11-carboxyhydrazide.

[0063] 4. Weigh 10H-indo[3,2-b]quinoline-11-formylhydrazide (166.0 mg, 0.6 mmol) and 3-methylbutyraldehyde (1.2 equivalents, 0.72 mmol), dissolve them in ethanol (15 mL), add concentrated HCl (1% equivalent), and heat under reflux at 80 °C for 6 h. The synthetic route is as follows:

[0064] Among them, R 1 for R 2To H. After the reaction was completed, it was cooled to room temperature, and the precipitate was collected by filtration, washed with ethanol and diethyl ether four to five times, and air-dried to obtain a yellow solid 147 mg, yield 71%, melting point: 252-253°C. 1 H NMR (400 MHz, DMSO-d6) δ 11.98 (s, 1H), 11.68 (s, 1H), 11.33 (s, 1H), 8.39 (t, J = 7.2 Hz, 1H), 8.32-8.22 (m, 1H), 8.11 (t, J = 7.8 Hz, 1H), 7.97 (t, J = 8.1 Hz, 1H), 7.78-7.55 (m, 7H), 7.49-7.44 (m, 1H), 7.38-7.27 (m, 1H), 2.71-2.54 (m, 1H), 1.40 (d, J = 8.3 Hz, 1H), 1.23-1.10 (m, 6H), 0.76 (d, J = 8.3 Hz, 1H), 0.67 (t, J = 7.6 Hz, 2H). 13 C NMR (100 MHz, DMSO-d6) δ 167.6, 161.7, 157.8, 154.5, 146.9, 146.4, 145.0, 144.9, 143.5, 130.7, 130.5, 129.7, 129.6, 126.7, 126.4, 125.9, 125.2, 124.7, 123.3, 123.2, 121.9, 121.8, 121.0, 120.3, 120.1, 120.1, 119.3, 112.4, 112.1, 31.6, 30.9, 20.0, 19.7. HRMS, calculated for C 21 H 21 N4O + [M+H] + 345.1710, found 345.1704.

[0065] Example 2

[0066] A queonyl hydrazone structure containing quebrachamine derivative (structure formula is shown in formula (I-2))

[0067] The preparation method is basically the same as that in Example 1, except that the reaction raw material in step 4 is R 1 is R 2 is H. This embodiment finally obtains a yellow solid 146 mg, yield 74%, melting point: greater than 250°C. 1H NMR (400MHz, DMSO-d6) δ11.98(d,J=39.0Hz,1H),11.65(s,1H),11.44(s,1H),8.88(d,J=7.0H z,1H),8.40(d,J=7.2Hz,1H),8.28(t,J=6.9Hz,1H),8.11(t,J=8.2Hz,1H),7.94(d,J=8.4Hz, 1H),7.77-7.58(m,5H),7.35(t,J=6.4Hz,1H),7.22(d,J=6.7Hz,1H),7.07(d,J=6.1Hz,1H),1 .81(s,1H),0.99(d,J=7.9Hz,2H),0.78(d,J=2.1Hz,2H),0.63(d,J=7.8Hz,1H),0.42(s,1H). 13 C NMR (100MHz, DMSO-d6) δ161.1,156.5,153.9,153.0,146.8,145.0,144.9,143.5,130.7,130.6,129.6,129.5,129.4,126.8,126.6,126.4 ,126.1,125.0,124.7,123.4,123.1,121.9,121.1,121.0,120.3,120.2,119.3,112.3,25.7,25.2,14.1,13.7,6.7,6.4.HRMS,calculated for C 20 H 17 N4O + [M+H] + 329.1397, found 329.1399.

[0068] Example 3

[0069] A derivative of leucocele containing an acylhydrazone structure (structure shown in formula (I-3))

[0070] The preparation method is basically the same as in Example 1, except that the reaction raw materials in step 4 are different. In the middle, R 1 for R 2 H was obtained. In this embodiment, 89 mg of an orange-red solid was finally obtained, with a yield of 71% and a melting point greater than 250°C. 1H NMR (400 MHz, DMSO-d6) δ 12.79 (s, 1H), 12.56 (s, 1H), 12.15 (s, 1H), 8.72 (d, J = 7.8 Hz, 1H), 8.59 (d, J = 7.8 Hz, 1H), 8.52 (d, J = 8.5 Hz, 1H), 8.44 (d, J = 8.5 Hz, 1H), 8.38 (s, 1H), 8.28 - 8.23 (m, 1H), 8.11 (d, J = 8.4 Hz, 1H), 7.95 - 7.89 (m, 1H), 7.89 - 7.81 (m, 2H), 7.80 - 7.72 (m, 2H), 7.69 - 7.62 (m, 1H), 7.52 (d, J = 6.3 Hz, 2H), 7.45 - 7.37 (m, 1H), 7.22 (t, J = 7.1 Hz, 1H), 7.14 (t, J = 7.5 Hz, 1H), 7.07 (d, J = 7.7 Hz, 1H). 13 C NMR (100 MHz, DMSO-d6) δ 166.3, 160.8, 149.0, 145.9, 145.2, 145.0, 133.9, 133.5, 132.3, 131.6, 130.5, 130.0, 129.7, 129.2, 129.0, 128.6, 127.8, 127.3, 126.8, 126.7, 126.5, 125.1, 124.6, 123.2, 122.7, 122.5, 122.3, 120.6, 120.4, 112.3, 112.2. HRMS, calculated for C 23 H 17 N4O + [M+H] + 365.1397, found 365.1398.

[0071] Example 4

[0072] The preparation method is basically the same as that in Example 1, except that the raw material of step 4 is

[0073] The preparation method is basically the same as that in Example 1, except that the raw material of step 4 is 1 R R 2 is H. This example finally obtains 150 mg of orange solid, with a yield of 66%, and a melting point of more than 250°C. 1 ​H NMR(400MHz,DMSO-d6)δ12.54(s,1H),12.39(s,1H),11.80(s,1H),8.51(d,J =7.5Hz,1H),8.45(d,J=7.8Hz,1H),8.36(d,J=12.0Hz,1H),8.31(s,1H),8.2 3-8.17(m,1H),8.04(d,J=8.4Hz,1H),7.82-7.75(m,1H),7.75-7.65(m,4H), 7.65-7.56(m,1H),7.40-7.31(m,3H),6.95(s,1H),2.38(s,2H),2.14(s,1H). 13 C NMR (100MHz, DMSO-d6) δ161.5,149.2,146.1,145.7,145.4,145.2,140.8,140.3,131.8,131.4,130.1,129.9,129.7,129.5,12 8.4,127.8,127.5,127.0,126.8,125.4,124.9,123.3,123.0,122.4,120.7,120.6,120.0,112.5,21.6,21.3.HRMS,calculated for C 24 H 19 N4O + [M+H] + 379.1553, found 379.1553.

[0074] Example 5

[0075] A derivative of leucocephaline containing an acylhydrazone structure (structure shown in formula (I-5))

[0076] The preparation method is basically the same as in Example 1, except that the reaction raw materials in step 4 are different. In the middle, R 1 for R 2 The final product was H. This example yielded 118 mg of a yellow solid, with a yield of 70% and a melting point greater than 250°C. 1H NMR (400 MHz, DMSO-d6) δ 12.49 (s, 1H), 12.33 (s, 1H), 11.78 (s, 1H), 8.51 (d, J = 6.5 Hz, 1H), 8.45 (d, J = 7.5 Hz, 1H), 8.39 - 8.28 (m, 2H), 8.23 - 8.15 (m, 1H), 8.04 (d, J = 8.3 Hz, 1H), 7.84 - 7.73 (m, 3H), 7.73 - 7.56 (m, 3H), 7.35 (t, J = 7.2 Hz, 1H), 7.08 (d, J = 8.3 Hz, 2H), 7.01 (d, J = 8.3 Hz, 1H), 6.71 (d, J = 8.4 Hz, 1H), 3.84 (s, 2H), 3.63 (s, 1H). 13 C NMR (100 MHz, DMSO-d6) δ 161.6, 161.1, 148.9, 146.2, 145.7, 145.2, 131.1, 129.8, 129.4, 129.0, 128.6, 127.2, 127.1, 126.7, 126.6, 126.5, 125.4, 124.9, 123.4, 123.0, 122.2, 120.5, 114.9, 114.6, 112.5, 55.8, 55.6. HRMS, calculated for C 24 H 19 N4O2 + [M+H] + 395.1503, found 395.1502.

[0077] Example 6

[0078] The preparation method is basically the same as that in Example 1, except that the raw material of step 4 is

[0079] The preparation method is basically the same as that in Example 1, except that the raw material of step 4 is 1 R R 2 is H. This example finally obtains 121 mg of orange solid, with a yield of 71%, and a melting point of more than 250 °C. 1 ​H NMR (400MHz, DMSO-d6) δ13.04(s,1H),12.82(s,1H),12.59(s,1H),8.98(d,J=7.9Hz,1H),8.86 (d,J=7.8Hz,1H),8.72(d,J=8.6Hz,1H),8.64(d,J=8.4Hz,1H),8.41(s,1H),8.33(d,J=8.5Hz,1 H),8.28(s,1H),8.17(d,J=8.4Hz,1H),8.08-7.97(m,1H),7.88(d,J=8.1Hz,4H),7.71(t,J=8.4 Hz,1H),7.60(d,J=8.2Hz,1H),7.52-7.43(m,1H),7.21(d,J=8.2Hz,1H),7.10(d,J=8.3Hz,1H). 13 C NMR(100MHz,DMSO-d6)δ166.0,160.5,148.7,146.2,146.0,145.7,141.6,13 9.7,137.7,135.6,135.1,134.1,133.5,133.3,132.7,130.8,130.7,130.0, 129.6,129.6,129.3,128.7,128.0,127.9,125.9,125.5,124.8,124.2,123. 9,123.0,122.5,122.3,121.6,121.4,116.5,113.2,113.1.HRMS,calculated for C 23 H 16 ClN4O + [M+H] + 399.1007, found 399.1008.

[0080] Example 7

[0081] A derivative of leucocephaline containing an acylhydrazone structure (structure shown in formula (I-7))

[0082] The preparation method is basically the same as in Example 1, except that the reaction raw materials in step 4 are different. In the middle, R 1 for R 2 H was used. In this example, 179 mg of orange solid was finally obtained, with a yield of 67% and a melting point greater than 250°C. 1H NMR (400MHz, DMSO-d6) δ12.89(s,1H),12.67(s,1H),12.21(s,1H),8.77(d,J=7.8Hz,1 H),8.62(d,J=7.8Hz,1H),8.56(d,J=8.5Hz,1H),8.46(d,J=8.5Hz,1H),8.37(s,1H),8 .26(d,J=9.1Hz,1H),8.11(d,J=8.4Hz,1H),7.94(t,1H),7.88(t,1H),7.84-7.71(m,5 H),7.70-7.63(m,1H),7.47-7.38(m,1H),7.35(d,J=8.3Hz,1H),7.03(d,J=8.4Hz,1H). 13 C NMR(100MHz,DMSO-d6)δ166.7,161.2,148.3,145.8,145.6,145.4,133.7,133.2,132.5,132.2,132.2,130.2,129.7,128.9, 128.5,127.4,127.3,125.6,125.1,124.3,123.9,123.8,123.2,122.7,121.2,121.0,118.7,112.9,112.8.HRMS,calculated for C 23 H 16 BrN4O + [M+H] + 443.0502, found 443.0503.

[0083] Example 8

[0084] A derivative of leucovorin containing an acylhydrazone structure (structure shown in formula (I-8))

[0085] The preparation method is basically the same as in Example 1, except that the reaction raw materials in step 4 are different. In the middle, R 1 for R 2 H was obtained. In this example, 197 mg of a brownish-green solid was finally obtained, with a yield of 80% and a melting point greater than 250°C. 1H NMR (400 MHz, DMSO-d6) δ 12.39 (s, 1H), 12.18 (s, 1H), 11.90 (s, 1H), 8.59 (d, J = 7.8 Hz, 1H), 8.49 (d, J = 7.8 Hz, 1H), 8.42 (d, J = 8.5 Hz, 1H), 8.35 (d, J = 8.2 Hz, 1H), 8.21 (d, J = 6.6 Hz, 2H), 8.06 (d, J = 10.4 Hz, 1H), 7.86 - 7.77 (m, 1H), 7.74 - 7.67 (m, 2H), 7.66 - 7.59 (m, 3H), 7.41 - 7.33 (m, 1H), 6.88 (d, J = 8.9 Hz, 1H), 6.81 (d, J = 8.9 Hz, 2H), 6.44 (d, J = 9.0 Hz, 1H), 3.01 (s, 5H), 2.79 (s, 2H). 13 C NMR (100 MHz, DMSO-d6) δ 171.8, 160.3, 151.6, 149.4, 144.9, 131.2, 129.5, 129.1, 128.7, 127.8, 127.4, 126.4, 126.4, 125.2, 124.6, 122.9, 122.2, 121.3, 120.2, 112.2, 112.1, 111.9, 111.7, 56.0, 49.4, 26.0, 18.5. HRMS, calculated for C 25 H 22 N5O + [M+H] + 408.1819, found 408.1820.

[0086] Example 9

[0087] The preparation method is basically the same as that in Example 1, except that the raw material of step 4 is

[0088] The preparation method is basically the same as that in Example 1, except that the raw material of step 4 is 1 2 This example finally obtained 140 mg of yellow solid, yield 75%, melting point: more than 250 °C. 1 ​​​H NMR (400MHz, DMSO-d6) δ12.74(s,1H),12.50(s,1H),12.21(d,J=40.3Hz,1H),8.73(d,J=7.4Hz,1H), 8.61(d,J=7.5Hz,1H),8.53(d,J=8.6Hz,1H),8.45(d,J=8.4Hz,1H),8.23(d,J=7.9Hz,1H),8.14-8.0 7(m,1H),7.93(d,J=8.6Hz,1H),7.88(t,J=7.5Hz,1H),7.82-7.73(m,2H),7.66(d,J=8.2Hz,1H),7.4 8(s,1H),7.46-7.38(m,1H),7.05(d,J=3.2Hz,1H),6.71(s,1H),6.67(d,J=3.1Hz,1H),6.42(s,1H). 13 C NMR(100MHz,DMSO-d6)δ160.3,149.1,148.3,145.8,145.2,138.7,136.2,132.8,132.1,129.8,129.5,129.2,128.4, 127.1,126.9,125.2,124.7,123.6,122.9,122.7,122.2,120.8,120.6,114.6,112.5,112.4,111.9.HRMS,calculated for C 21 H 15 N4O2 + [M+H] + 355.1190, found 355.1189.

[0089] Example 10

[0090] A derivative of leucocele containing an acylhydrazone structure (structure shown in formula (I-10))

[0091] The preparation method is basically the same as in Example 1, except that the reaction raw materials in step 4 are different. In the middle, R 1 for R 2 The final product was H. This example yielded 145 mg of a yellow solid, with a yield of 76% and a melting point greater than 250°C. 1H NMR (400 MHz, DMSO-d6) δ 12.62 (d, J = 29.9 Hz, 1H), 11.76 (s, 1H), 11.48 (s, 1H), 8.97 (s, 1H), 8.68 (s, 1H), 8.40 (d, J = 3.4 Hz, 2H), 8.33 - 8.21 (m, 2H), 8.18 (d, J = 8.3 Hz, 1H), 7.99 (d, J = 8.4 Hz, 1H), 7.78 - 7.72 (m, 1H), 7.68 (t, J = 7.6 Hz, 2H), 7.61 (d, J = 7.9 Hz, 1H), 7.58 - 7.52 (m, 1H), 7.38 - 7.30 (m, 1H), 7.17 - 7.10 (m, 1H). 13 C NMR (100 MHz, DMSO-d6) δ 167.8, 161.7, 151.0, 150.3, 148.9, 148.0, 146.5, 146.1, 145.8, 144.5, 144.4, 143.1, 142.9, 142.2, 133.7, 132.9, 130.3, 130.1, 130.0, 129.3, 129.2, 128.6, 126.3, 126.1, 125.7, 124.5, 124.2, 123.7, 122.8, 122.7, 121.4, 120.6, 119.9, 119.8, 119.1, 118.1, 112.5, 111.9, 111.7. HRMS, calculated for C 22 H 16 N5O + [M+H] + 366.1349, found 366.1348.

[0092] Example 11

[0093] The preparation method is basically the same as that in Example 1, except that the raw material of step 4 is

[0094] The preparation method is basically the same as that in Example 1, except that the raw material of step 4 is 1 R R 2 is H. This example finally obtains 188 mg of red solid, with a yield of 78%, and a melting point of more than 250 °C. 1 ​H NMR (400 MHz, DMSO-d6) δ 12.68 (s, 1H), 12.39 (s, 1H), 11.81 (s, 1H), 11.49 (s, 1H), 9.11-9.00 (m, 1H), 8.95-8.86 (m, 1H), 8.77 (t, J = 8.5 Hz, 1H), 8.66 (t, J = 8.4 Hz, 1H), 8.57 (d, J = 5.7 Hz, 1H), 8.46 (d, J = 6.8 Hz, 1H), 8.42-8.34 (m, 1H), 8.25 (d, J = 8.3 Hz, 1H), 8.04 (d, J = 6.8 Hz, 1H), 7.95 (s, 1H), 7.91-7.78 (m, 2H), 7.73 (d, J = 10.5 Hz, 1H), 7.67 (d, J = 8.2 Hz, 1H), 7.54-7.44 (m, 1H), 7.30-7.22 (m, 1H), 7.18 (d, J = 8.0 Hz, 1H), 6.82 (t, J = 7.5 Hz, 1H), 6.05 (t, J = 6.9 Hz, 1H), 5.72 (d, J = 7.5 Hz, 1H). 13 C NMR (100 MHz, DMSO-d6) δ 164.5, 158.7, 146.7, 145.8, 145.7, 142.7, 138.4, 137.2, 136.6, 133.7, 133.4, 131.6, 130.7, 130.4, 129.5, 127.6, 127.4, 125.6, 125.4, 124.6, 124.3, 123.4, 122.8, 122.7, 122.2, 122.0, 122.0, 121.1, 121.0, 120.7, 120.0, 119.3, 114.4, 112.9, 112.8, 112.0, 111.6, 111.2, 110.8. HRMS calculated for C 25 H 18 N5O + [M+H] + 404.1506, found404.1502.

[0095] Example 12

[0096] Arohygine derivative containing acylhydrazone structure (structure formula is shown in formula (I-12))

[0097] The preparation method is basically the same as that in Example 1, except that the raw material of step 4 is , R 1 and R 2 are The final product of this example is a yellow solid 120 mg, yield 68%, melting point: 239-240 °C. 1 H NMR (400 MHz, DMSO-d6) δ 11.62 (s, 1H), 11.39 (s, 1H), 11.29 (s, 1H), 11.09 (s, 1H), 8.36 (t, J = 7.1 Hz, 1H), 8.29 - 8.19 (m, 1H), 8.06 (d, J = 8.1 Hz, 1H), 7.90 (d, J = 8.2 Hz, 1H), 7.73 - 7.67 (m, 1H), 7.67 - 7.60 (m, 2H), 7.59 - 7.54 (m, 1H), 7.34 - 7.27 (m, 1H), 2.41 (q, J = 14.8, 7.4 Hz, 2H), 2.37 - 2.31 (m, 1H), 1.85 (q, J = 14.3, 7.1 Hz, 1H), 1.16 (t, J = 7.4 Hz, 3H), 1.07 - 0.97 (m, 4H). 13 C NMR (100 MHz, DMSO-d6) δ 168.2, 165.1, 161.7, 159.5, 146.3, 145.9, 144.5, 144.3, 143.1, 142.9, 130.0, 129.9, 129.2, 129.2, 129.0, 128.4, 126.1, 125.8, 125.7, 125.2, 124.7, 124.2, 123.2, 122.6, 121.3, 121.2, 120.7, 120.6, 119.7, 119.5, 111.8, 111.6, 47.9, 47.5, 33.3, 32.4, 29.1, 28.2, 25.3, 25.2, 24.7, 24.4, 22.7, 22.5, 10.7, 10.1, 10.0, 9.6. HRMS calculated for C 21 H 21 N4O + [M+H] + 345.1710, found 345.1707.

[0098] Example 13

[0099] The white-leafed tylophora alkaloid derivative containing acylhydrazone structure (the structural formula is shown in formula (I-13))

[0100] The preparation method is basically the same as that in Example 1, except that the raw material of step 4 is , R 1 and R 2 are combined into The final product of this example is an orange solid 138 mg, yield 70%, melting point: greater than 250 °C.1 H NMR (400 MHz, DMSO-d6) δ 11.58 (s, 1H), 11.45 (s, 1H), 11.42 (s, 1H), 11.29 (s, 1H), 8.37 (d, J = 7.7 Hz, 1H), 8.25 (t, J = 8.1 Hz, 1H), 8.08 (d, J = 8.2 Hz, 1H), 7.90 (d, J = 8.3 Hz, 1H), 7.73 - 7.56 (m, 5H), 7.31 (t, J = 7.2 Hz, 1H), 3.02 (t, J = 7.7 Hz, 2H), 2.93 (t, J = 7.9 Hz, 1H), 2.54 (t, J = 7.9 Hz, 1H), 1.95 (t, J = 8.0 Hz, 1H), 1.83 (t, 1H). 13 C NMR (100 MHz, DMSO-d6) δ 167.9, 162.5, 161.6, 158.3, 146.8, 146.5, 145.0, 144.9, 143.6, 143.5, 130.6, 130.5, 129.6, 129.6, 128.7, 126.6, 126.5, 126.2, 126.0, 124.9, 124.8, 123.6, 123.0, 121.8, 121.2, 121.1, 121.0, 120.2, 120.1, 119.7, 112.3, 112.2, 34.5, 34.2, 34.0, 33.7, 13.6, 13.4. HRMS calculated for C 20 H 17 N4O + [M+H] + 329.1397, found 329.1397.

[0101] Example 14

[0102] The acylhydrazone-structure-containing alstonia isolaricina derivative (the structural formula is shown in formula (I-14))

[0103] The preparation method is basically the same as that in Example 1, except that the reaction raw material in step 4 is , R 1 and R 2 are combined into This example finally obtains 145 mg of yellow solid, the yield is 68%, the melting point is greater than 250°C. 1H NMR (400 MHz, DMSO-d6) δ 11.60 (s, 1H), 11.42 (s, 1H), 11.34 (s, 1H), 11.22 (s, 1H), 8.39-8.33 (m, 1H), 8.24 (t, J = 9.3 Hz, 1H), 8.10-8.05 (m, 1H), 7.91 (d, J = 8.3 Hz, 1H), 7.72-7.67 (m, 1H), 7.66-7.60 (m, 2H), 7.60-7.54 (m, 1H), 7.34-7.27 (m, 1H), 2.44-2.37 (m, 3H), 1.72 (d, J = 7.0 Hz, 3H), 1.60 (s, 4H). 13 C NMR (100 MHz, DMSO-d6) δ 163.9, 161.7, 146.3, 145.9, 144.5, 144.4, 143.1, 143.0, 130.0, 129.9, 129.2, 129.1, 126.1, 125.9, 125.7, 125.4, 124.6, 124.3, 123.1, 122.6, 121.3, 120.6, 119.7, 119.5, 111.8, 111.6, 35.1, 34.8, 33.3, 28.0, 27.9, 26.9, 26.8, 25.7, 25.6, 25.3, 25.0, 25.0, 24.4. HRMS calculated for C 22 H 21 N4O + [M+H] + 357.1710, found 357.1707.

[0104] Example 15

[0105] The preparation method is basically the same as that in Example 1, except that the raw material for the reaction in step 4 is

[0106] The preparation method is basically the same as that in Example 1, except that the raw material for the reaction in step 4 is 1 2 This example finally obtained 172 mg of orange solid, yield 76%, melting point: more than 250 °C. 1 ​​​H NMR (400 MHz, DMSO-d6) δ 12.07 (s, 1H), 11.96 (s, 1H), 11.54 (s, 1H), 8.65 (d, J = 6.8 Hz, 1H), 8.58 (d, J = 7.1 Hz, 1H), 8.49 - 8.41 (m, 1H), 8.24 (d, J = 8.4 Hz, 1H), 8.09 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 6.1 Hz, 1H), 7.90 - 7.81 (m, 1H), 7.79 - 7.69 (m, 2H), 7.67 - 7.60 (m, 1H), 7.50 (d, J = 6.0 Hz, 2H), 7.43 - 7.36 (m, 1H), 7.11 (t, J = 6.2 Hz, 1H), 7.03 - 6.94 (m, 2H), 2.40 (s, 1H), 2.36 (s, 2H). 13 C NMR (100 MHz, DMSO-d6) δ 168.0, 162.0, 155.1, 150.6, 145.5, 140.5, 138.5, 132.3, 131.8, 130.3, 130.1, 129.5, 129.4, 129.0, 128.5, 127.0, 127.0, 126.1, 125.5, 125.2, 123.5, 123.3, 122.9, 122.8, 120.9, 120.8, 112.7, 100.0, 15.3, 14.7. HRMS, calculated for C 24 H 19 N4O + [M+H] + 379.1553, found 379.1552.

[0107] Example 16

[0108] The acylhydrazone-structure-containing alstonia isolariva derivative (the structural formula is shown in formula (I-16))

[0109] The preparation method is basically the same as that in Example 1, except that the reaction raw material in step 4 is R 1 is R 2 is CH3. This example finally obtains 181 mg of yellow solid, the yield is 74%, and the melting point is greater than 250°C. 1H NMR (400 MHz, DMSO-d6) δ 11.97 (s, 1H), 11.85 (s, 1H), 11.45 (s, 1H), 8.59 (d, J = 29.8 Hz, 1H), 8.49 - 8.35 (m, 1H), 8.23 (s, 1H), 8.06 (s, 1H), 7.92 (s, 1H), 7.83 (s, 1H), 7.71 (s, 2H), 7.65 (d, J = 8.8 Hz, 1H), 7.38 (s, 1H), 7.05 (s, 1H), 6.95 (s, 1H), 6.53 (s, 1H), 3.83 (s, 2H), 3.57 (s, 1H), 2.36 (s, 3H). 13 C NMR (100 MHz, DMSO-d6) δ 161.9, 161.7, 161.0, 160.4, 155.0, 150.4, 145.4, 131.9, 131.5, 130.9, 130.8, 130.4, 130.2, 129.3, 128.6, 127.8, 127.6, 126.8, 125.5, 125.1, 123.6, 123.1, 122.8, 122.6, 120.7, 120.6, 114.3, 113.9, 112.6, 55.8, 55.5, 15.1, 14.5. HRMS calculated for C 25 H 21 N4O2 + [M+H] + 409.1659, found 409.1658.

[0110] Comparative Example 1

[0111] Weighed 10H-indolo[3,2-b]quinoline-11-carbohydrazide (166.0 mg, 0.6 mmol) and 3-methylbutanal (1.2 eq, 0.72 mmol) were dissolved in ethanol (15 mL) without concentrated hydrochloric acid, heated to reflux at 80 °C for 20 h, the synthesis path is as follows:

[0112] Cool to room temperature, filter to collect the precipitate, wash with ethanol and ether four to five times, dry, get yellow solid, yield 30%.

[0113] Comparative Example 2

[0114] 10H-indolo[3,2-b]quinoline-11-carboxylic acid (1 mmol) with propargylamine (1.1 mmol) in 1-hydroxybenzotriazole (1.1 mmol), 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.1 mmol) under the condition of using N,N-dimethylformamide as solvent, after the reaction, ethyl acetate extraction, saturated brine washing, anhydrous sodium sulfate drying, and concentration, to obtain the amide compound. The obtained amide compound (1 mmol) with benzyl azide (1 mmol) in cuprous bromide (1.2 mmol), N-ethyldiisopropylamine (2 mmol) under the condition of using methanol as solvent, using nitrogen protection and avoiding light reaction overnight, detecting by TLC until the reaction is completed, using ethyl acetate extraction, saturated brine washing, anhydrous sodium sulfate drying, and concentration to obtain a yellow solid, yield 60%, melting point: 226-227°C; 1 H NMR (400 MHz, DMSO-d6) δ 11.54 (s, 1H), 9.47 (t, J = 5.7 Hz, 1H), 8.36 (d, J = 7.7 Hz, 1H), 8.26-8.19 (m, 2H), 8.07 (d, J = 8.4 Hz, 1H), 7.71-7.60 (m, 3H), 7.55 (t, J = 7.6 Hz, 1H), 7.41-7.29 (m, 6H), 5.65 (s, 2H), 4.76 (d, J = 5.6 Hz, 2H); 13 C NMR (100 MHz, DMSO-d6) δ 165.6, 146.7, 145.3, 144.8, 143.6, 136.6, 130.6, 129.6, 129.3, 129.2, 128.6, 128.4, 126.6, 126.0, 124.8, 123.6, 123.1, 121.8, 121.1, 120.7, 120.2, 112.2, 53.3, 35.5; HRMS calcd. for C 26 H 21 N6O + [M+H] + :433.1771; found: 433.1769.

[0115] Experimental Example 1

[0116] The determination of the anti-tobacco mosaic virus activity was carried out according to the following procedure:

[0117] 1. Virus purification and concentration determination:

[0118] After the crude virus solution was treated by polyethylene glycol centrifugation twice, the absorbance value (A 260 ) at 260 nm wavelength was determined by using ultraviolet spectrophotometer, and the virus concentration was calculated according to the following formula.

[0119] Virus concentration (mg / mL) = (A 260 x dilution factor) / E 0.1％ 1cm 260nm

[0120] Wherein E represents the extinction coefficient, i.e. the optical absorption (optical density) value of a suspension with a concentration of 0.1% (1 mg / ml) at a wavelength of 260 nm and an optical path of 1 cm.

[0121] E of TMV (tobacco mosaic virus) 0.1％ 1cm 260nm is 3.1, which is stored in a refrigerator at 4°C for standby.

[0122] 2. Preparation of the solution of the compound to be tested:

[0123] After weighing, the compound and the raw anilin compound are dissolved in DMF to prepare a 1 x 10 5 μg / mL stock solution, which is then diluted to the required concentration with a 1‰ aqueous solution of Tween 80.

[0124] 3. In vivo passivation:

[0125] After mixing the solution of the compound to be tested with an equal volume of the virus juice (20 μg / mL) for passivation for 30 minutes, 3-5 leaf stage Candelas tobacco with the same growth vigor is rubbed for inoculation, and then washed with running water. A 1‰ aqueous solution of Tween 80 is used as a control. After 3 days, the control effect is calculated according to the number of lesions. Each treatment is repeated 3 times.

[0126] 4. In vivo treatment:

[0127] After the whole leaves of 3-5 leaf stage Candelas tobacco with the same growth vigor are inoculated with the virus (10 μg / mL) using a brush, the leaves are washed with running water. After the leaf surface is dried, the whole plant is sprayed with the drug, and a 1‰ aqueous solution of Tween 80 is used as a control. After 3 days, the control effect is calculated according to the number of lesions. Each treatment is repeated 3 times.

[0128] 5. In vivo protection:

[0129] The whole plant of 3-5 leaf stage Candelas tobacco with the same growth vigor is sprayed with the drug, and a 1‰ aqueous solution of Tween 80 is used as a control. After 24 hours, the leaf surface is covered with emery (500 mesh), and then the virus solution (10 μg / mL) is lightly rubbed on the whole leaf surface along the vein direction using a brush twice. After inoculation, the leaves are washed with running water. After 3 days, the control effect is calculated according to the number of lesions. Each treatment is repeated 3 times.

[0130] Inhibition rate (%) = [(control number of dead spots - treatment number of dead spots) / control number of dead spots] x 100%

[0131] Firstly, the anti-tobacco mosaic virus activity of all compounds was tested in vivo at a treatment dose of 500 μg / mL. Compounds with a relative inhibition rate greater than 40% were then tested for in vivo treatment and activity protection activity at a treatment dose of 500 μg / mL. The positive control was the commercial anti-plant virus agent Anisomycin.

[0132] The results of the anti-tobacco mosaic virus (TMV) activity tests of the acylhydrazone structure-containing quebrachine derivatives of Examples 1 to 16 and Anisomycin are shown in Table 1 below:

[0133] Table 1

[0134]

[0135] As can be seen from the data in Table 1, the acylhydrazone structure-containing quebrachine derivatives showed good anti-TMV activity at 500 μg / mL. The acylhydrazone structure-containing quebrachine derivative of structural formula I-1 showed anti-TMV activity comparable to that of the commercial Anisomycin, and the acylhydrazone structure-containing quebrachine derivative of structural formula I-15 showed better in vivo passivation activity than Anisomycin.

[0136] Experimental Example 2

[0137] The test procedure for antibacterial activity is as follows:

[0138] Rice sheath blight pot activity

[0139] Rice seedlings with uniform growth were selected and treated with foliar spraying at the desired concentration, and a blank control was set up by spraying water. Each treatment was repeated twice. 24 h after treatment, the rice seedlings were inoculated with rice sheath blight spores, and then placed in a greenhouse (25°C ± 4°C) for normal management. The control effect was observed visually 6 days after inoculation. The results of the in vivo fungicidal activity tests of the acylhydrazone structure-containing quebrachine derivatives of Examples 1 to 16 are shown in Table 2 below:

[0140] Table 2

[0141]

[0142] As can be seen from the data in Table 2, the compounds of Examples 1 to 16 showed bacteriostatic activity against rice sheath blight in the in vivo pot experiment.

[0143] It should be noted that, in Table 1 and Table 2, I-1 is used as an example for explanation, which represents an acylhydrazone structure-containing quebrachine derivative of formula I-1; the meanings of I-2 to I-16 in Table 1 and Table 2 are as explained above.

[0144] It should be pointed out finally that the above embodiments are only used to illustrate the technical solutions of the present application, but not to limit the same; and although the present application has been described in detail with reference to the foregoing embodiments, it should be appreciated by those skilled in the art that the technical solutions recorded in the foregoing embodiments can be modified, or some technical features thereof can be replaced equivalently; and these modifications or replacements do not make the essence of the corresponding technical solutions deviate from the spirit and scope of the technical solutions of the embodiments of the present application.

Claims

1. A quebrachamine derivative containing an acylhydrazone structure, characterized by, The white-leafed tylophora alkaloid derivative containing an acylhydrazone structure is selected from at least one of the structural formulas as shown in formulas (I-1) to (I-16): 。 2. A process for preparing a furogen-containing quebrachamine derivative according to claim 1, characterized by, The preparation method comprises the following steps: make and The reaction yielded the white vine alkaloid derivative containing the acylhydrazone structure; wherein R 1 is selected from at least one of , , , , , , , , , , and R 2 is selected from at least one of hydrogen, methyl and ethyl; or R 1 and R 2 combined to or .

3. The method for preparing the leucocephalan alkaloid derivative containing an acylhydrazone structure according to claim 2, characterized in that, The preparation method comprises the following steps: Will and Dissolve in ethanol, add 1%~3% molar equivalent of concentrated HCl was heated under reflux at 70~90 °C for 5~7 h. After the reaction was completed, the mixture was cooled, washed and dried in sequence to obtain the acetylhydrazone-containing leucocele alkaloid derivative.

4. The method for preparing the leucocephalan alkaloid derivative containing an acylhydrazone structure according to claim 3, characterized in that, and in a molar ratio of 4 to 6: 5 to 7.

5. The method for preparing the leucocele alkaloid derivative containing an acylhydrazone structure according to claim 3, characterized in that, The washing comprises: washing the obtained solid product after cooling with ethanol and diethyl ether for four to five times.

6. Use of a quebrachamine derivative containing an acylhydrazone structure according to claim 1 for the treatment of plant viral diseases, characterized in that, The virus is tobacco mosaic virus.

7. Use of the acylhydrazone-containing quebrachamine derivative according to claim 1 for antibacterial purposes, characterized in that, The application in the antibacterial aspect is the application in rice sheath blight.

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