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CN112174954A - Beta-carboline amide compound containing beta-arylamine and application of beta-carboline amide compound as agricultural bactericide - Google Patents

Beta-carboline amide compound containing beta-arylamine and application of beta-carboline amide compound as agricultural bactericide Download PDF

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CN112174954A
CN112174954A CN201910597143.8A CN201910597143A CN112174954A CN 112174954 A CN112174954 A CN 112174954A CN 201910597143 A CN201910597143 A CN 201910597143A CN 112174954 A CN112174954 A CN 112174954A
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carboline
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indole
arylamine
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李圣坤
来继星
李伟
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Nanjing Agricultural University
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    • C07—ORGANIC CHEMISTRY
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    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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    • 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
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Abstract

本发明涉及含β‑芳基胺的β‑咔啉酰胺类化合物及其抑制农作物病原菌的用途，该类化合物的化学结构式如下式(I)所示：

Figure DSA0000185446780000011
通式(I)中R1，R2，R3，R4，表示取代基；
Figure DSA0000185446780000012
表示芳香烃基，详见说明书部分。The present invention relates to β-carboline amide compounds containing β-arylamines and the use thereof for inhibiting crop pathogenic bacteria. The chemical structural formula of such compounds is shown in the following formula (I):
Figure DSA0000185446780000011
R 1 , R 2 , R 3 , R 4 in the general formula (I) represent substituents;
Figure DSA0000185446780000012
Indicates an aromatic hydrocarbon group, see the description section for details.

Description

Beta-carboline amide compound containing beta-arylamine and application of beta-carboline amide compound as agricultural bactericide
Technical Field
The invention relates to a novel beta-carboline amide compound containing beta-arylamine and application thereof as an agricultural bactericide; in particular to the application of the compounds in the prevention and treatment of plant fungal diseases, belonging to the technical field of pesticides.
Background
Amide compounds play an important role in the fields of pharmaceutical chemistry and pesticide chemistry, and are a classic and active class in the field of agricultural fungicide development. Succinate dehydrogenase inhibitors (SDHIs) are representative amide bactericides, a pharmacophore model (Phytopathology, 2013, 103(9)880-888) of the bactericides is constructed at present, the bactericides and analogues are small molecules with excellent activity and huge market development potential at present, and at present, as many as 23 bactericides which are successfully developed and commercialized aiming at the target are developed.
The natural product model not only provides various lead structures for the development of new pesticides, but also can be used as a probe to discover new targets of pesticides so as to promote the development of new pesticides (Pest Manag. Sci.2017, 73, 700-. In recent ten years, a series of amide drug molecules and pesticide candidate compounds are discovered based on beta-carboline alkaloids. Beta-carboline natural product Alangiobansinine separated from Alangium platanifolium leaves is reported to have the potential of inhibiting DNA and protein biosynthesis and can influence the accessory nervous system (Phytochemistry, 1995, 40 (3): 975-977.), but the research on specific biological activity, structure optimization and structure-activity relationship is not reported so far. Recent studies have shown that β -carboline amides can be used as internal guiding groups for C-H functionalization, such as alkynylation, arylation, etc. (j.am.chem.soc, 2017, 139, 1325-.
The research on novel amide molecules and structure-activity relationship based on a natural product Alangiobansinine is only reported, the natural product is taken as a model, and a novel beta-carboline amide compound containing beta-arylamine is obtained by condensing beta-carboline-1-carboxylic acid and a beta-arylamine compound, and the biological activity report of the compound is not reported so far. The invention designs and synthesizes a series of beta-carboline-1-amide compounds containing beta-arylamine, and finds that the compounds have an inhibiting effect on plant fungal diseases. The discovery of the compounds can enrich succinate dehydrogenase inhibitor bactericides and has positive significance for creating new pesticides.
Disclosure of Invention
The invention aims to solve the technical problem of providing a preparation method of a beta-carboline-1-amide compound containing beta-arylamine and application thereof in preventing and treating plant fungal diseases. The beta-carboline-1-amide compound containing beta-arylamine has good effect of inhibiting fungal diseases.
The beta-carboline-1-amide compound containing beta-arylamine has a structure shown in a general formula (I),
Figure BSA0000185446800000011
r in the general formula (I)1，R2，R3，R4Represents a substituent:
R1represents hydrogen, hydroxy, methoxy, 1-12 carbon alkoxy, benzyloxy, halogen (fluorine, chlorine, bromine);
R2represents hydrogen, hydroxyl, methoxy, alkoxy of 1 to 12 carbons, hydrocarbyl of 1 to 12 carbons;
R3represents hydrogen, a hydrocarbon group of 1 to 12 carbons, a hydroxymethylene group, a carboxyl group, a carboxylic acid methyl ester, a carboxylic acid ethyl ester;
R4represents hydrogen, hydroxyl, methoxy, alkoxy with 1-12 carbons, phenyl, pyridyl, furyl, thienyl;
Figure BSA0000185446800000021
represents phenyl, phenyl substituted by 1-6 carbon hydrocarbon radicals, phenyl substituted by halogen, phenyl substituted by 1-6 carbon hydrocarbon oxygen radicals, aliphatic chain carbon hydroxyl and alkyl; indole, 1-6 carbon hydrocarbyl substituted indole, halogen substituted indole, 1-6 carbon hydrocarbyloxy substituted indole, N- (1-6 carbon hydrocarbyl) -indole, N- (aryl) -indole, N- (arylsulfonyl) -indole; pyridine, 1-5 carbon alkyl substituted pyridine, halogen substituted pyridine, trifluoromethyl substituted pyridine, 1-5 carbon alkoxy substituted pyridine; thiophene; furan; a pyrazole.
The invention also provides a beta-carboline-1-amide compound containing beta-arylamine, which is shown in the general formula (I) and can be accepted in pesticide chemistry.
The compounds of the present invention can be chemically prepared according to the following synthetic routes.
Figure BSA0000185446800000022
The method mainly comprises the following three steps of reaction:
step 1, adding tryptamine, manganese dioxide, methyl glycolate and a 3A molecular sieve into a reaction system, stirring for 3 hours at room temperature, then refluxing and stirring for 6-8 hours, cooling to room temperature, filtering, concentrating the filtrate under reduced pressure, and performing silica gel column chromatography to obtain beta-carboline-1-methyl carboxylate (intermediate 1).
And 2, dissolving beta-carboline-1-carboxylic acid methyl ester (intermediate 1) in methanol, adding a sodium hydroxide aqueous solution (1M) under an ice bath condition, stirring for 5 hours at 50 ℃, tracking and monitoring by Thin Layer Chromatography (TLC), adding ethyl acetate and water after the reaction is completed, adjusting the pH to 5-6 by using hydrochloric acid, extracting by using ethyl acetate, and concentrating the extract under reduced pressure to obtain the beta-carboline-1-carboxylic acid (intermediate 2).
And 3, dissolving beta-carboline-1-carboxylic acid (1 time of the amount of) and beta-arylamine compounds (1 time of the amount of) in dichloromethane, adding 1-hydroxybenzotriazole (1.3 times of the amount of) under an ice bath condition, then adding 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (1.3 times of the amount of), stirring for reaction at room temperature, tracking and monitoring by TLC (thin layer chromatography), washing with water, a saturated sodium bicarbonate solution and a saturated sodium chloride solution respectively after the reaction is completed, drying with anhydrous sodium sulfate, evaporating the solvent under reduced pressure, and carrying out silica gel column chromatography to obtain the target product beta-carboline-1-amide 3.
The synthesis of the beta-1-carboline amide compound containing beta-arylamine provided by the invention has the characteristics of cheap and easily obtained raw materials, few synthesis steps and easiness in operation.
The beta-carboline-1-amide compound containing beta-arylamine related by the invention is preferably the following compound:
a first part:
Figure BSA0000185446800000031
a second part:
wherein R is1And substituents represented by Ar are as shown in the first part, R2、R3、R4The substituents represented are as follows:
Figure BSA0000185446800000041
the beta-carboline-1-amide compounds containing beta-arylamine provided by the invention have activity on plant pathogenic fungi, and comprise Rhizoctonia solani (Rhizoctonia solani), Rhizoctonia cerealis (Rhizoctonia cerealis), Sclerotium sclerotiorum (Sclerotinia sclerotiorum), Fusarium graminearum (Fusarium graminearum), Fusarium graminearum (Gaeumannomyces graminis), Botrytis cinerea (Botrytis cinerea), Phytophthora solani (Phytophthora infestans), Phytophthora capsici (Phytophora capsici), Phytophthora solani (Alternaria solani), Phytophthora oryzae (Fusarium fujikururi), Phytophthora solani (Fusarium solani), Pyricularia oryzae (Pyricularia oryzae).
Detailed Description
The invention will be further illustrated and understood by the following examples and results of activity assays, which are not intended to be limiting.
The first embodiment is as follows:
synthesis of beta-carboline-1-carboxylic acid (intermediate 2)
Respectively weighing tryptamine (3.2g, 20mmol) and molecular sieve (4g) in a clean and dry pear-shaped bottle, adding dioxane to dissolve, slowly adding manganese dioxide (17g) in ice bath, then dropwise adding methyl glycolate (2.7mL), reacting at room temperature for 3h, then refluxing for 8h, tracking and monitoring by Thin Layer Chromatography (TLC), filtering after the reaction is finished, washing filter residue with ethyl acetate for multiple times, evaporating filtrate to dryness and concentrating, and performing silica gel column chromatography (eluent: V)Petroleum ether/VEthyl acetate2: 1, 1% triethylamine) to obtain 1.3g of yellow solid beta-carboline-1-carboxylic acid methyl ester (intermediate 6) with the yield of 29%.
Weighing beta-carboline-1-carboxylic acid methyl ester 6(2.26g, 10mmol), dissolving in 30mL of methanol, slowly dropwise adding sodium hydroxide aqueous solution (10mL, 1M) under ice bath condition, stirring at 50 ℃ for 5h, after TLC monitoring reaction is finished, adding ethyl acetate 20mL and water 10mL, adjusting pH to 6-7 with hydrochloric acid, extracting with ethyl acetate for 3 times, drying with anhydrous sodium sulfate, evaporating to dryness under reduced pressure, and concentrating to obtain 1.9g of beta-carboline-1-carboxylic acid (intermediate 7), wherein the yield is 89%.
Figure BSA0000185446800000051
Example two: synthesis of Alangiobaussinine (3-1)
The intermediate beta-carboline-1-carboxylic acid (2) (212mg, 1mmol) and tryptamine (160mg, 1mmol) are added to the reaction system, the mixture is dissolved in 20mL dichloromethane, HOBt (175mg, 1.3mmol) and EDCi (250mg, 1.3mmol) are added under ice bath condition, the mixture is stirred at room temperature overnight, the reaction system is washed by water (10mL multiplied by 2), saturated sodium bicarbonate solution (10mL multiplied by 2) and saturated sodium chloride solution (10mL multiplied by 2), dried by anhydrous sodium sulfate, decompressed to remove solvent, and subjected to silica gel column chromatography (eluent: V petroleum ether/V ethyl acetate ═ 2: 1, 1% triethylamine) to obtain 3-1 yellow solid with yield of 64%.
Figure BSA0000185446800000052
1H NMR(400MHz，CDCl3)10.35(s，1H)，8.30-8.34(m，2H)，8.14(dd，J1＝7.96Hz，J2＝1.04Hz，2H)，8.09(s，br，1H)，8.06(d，J＝5.0Hz，1H)，7.69(dd，J1＝7.92Hz，J2＝1.12Hz，1H)，7.61-7.52(m，2H)，7.39(m，1H)，7.30(m，1H)，7.22(m，1H)，7.17-7.11(m，1H)，3.89(q，J＝7.88Hz，2H)，3.17(t，＝7.88Hz，3H).
ESI-MS，Calcd for C22H19N4O[M+H]+355.1559，found 355.1557。
Example three: synthesis of Compound (3-2)
The intermediate beta-carboline-1-carboxylic acid (2) (212mg, 1mmol) and phenethylamine (121mg, 1mmol) are added into a reaction system, the mixture is dissolved in 20mL dichloromethane, HOBt (175mg, 1.3mmol) and EDCi (250mg, 1.3mmol) are added under ice bath condition, the mixture is stirred at room temperature overnight, the reaction system is washed by water (10mL multiplied by 2), saturated sodium bicarbonate solution (10mL multiplied by 2) and saturated sodium chloride solution (10mL multiplied by 2), dried by anhydrous sodium sulfate, decompressed to remove solvent, and subjected to silica gel column chromatography (eluent: V petroleum ether/V ethyl acetate is 3: 1, 1% triethylamine) to obtain 3-2 yellow solid with yield of 75%.
Figure BSA0000185446800000053
1H NMR(400MHz，CDCl3)10.33(s，1H)，8.35(d，J＝5.04Hz，1H)，8.27(s，br，1H)，8.14(m，1H)，8.07(d，J＝5.08Hz，1H)，7.61-7.53(m，2H)，7.37-7.28(m，5H)，7.25(m，1H)，3.81(m，2H)，3.04(t，J＝7.32Hz，2H).
ESI-MS，Calcd for C20H18N3O[M+H]+316.1450，found 316.1446。
Example four: synthesis of Compound (3-3)
Adding an intermediate beta-carboline-1-carboxylic acid (2) (212mg, 1mmol) into a reaction system, dissolving in 10mL dichloromethane, dropwise adding oxalyl chloride (635mg, 5mmol) under ice bath, dropwise adding three drops of DMF, stirring at room temperature overnight, concentrating the reaction system, and evaporating to dryness; then the secondary amine (204mg, 1mmol) was dissolved in 5mL of dichloromethane, triethylamine 300uL (2mmol) was added, and then the acid chloride was added slowly under ice-bath and stirred at room temperature. The reaction system was washed with water (10mL × 2), dried over anhydrous sodium sulfate, evaporated under reduced pressure to remove the solvent, and subjected to silica gel column chromatography (eluent: V petroleum ether/V ethyl acetate 8: 1, 1% triethylamine) to obtain 3 to 3 yellow solids, which was obtained in a total yield of 51% in two steps.
Figure BSA0000185446800000061
1H NMR(400MHz，CDCl3)9.52(s，1H)，8.36(d，J＝5.04Hz，1H)，8.12(t，J＝7.84Hz，1H)，8.01(d，J＝5.00Hz，1H)，7.59(m，1H)，7.51(d，J＝8.24Hz，1H)，7.31(m，1H)，6.98(m，1H)，6.16(s，1H)，5.83(s，1H)，4.01(s，3H)，3.86(m，1H)，2.97(dd，J1＝13.88Hz，J2＝9.40Hz，1H)，2.73(dd，J1＝13.88Hz，J2＝4.44Hz，1H)，1.57(d，J＝6.60Hz，3H).
ESI-MS，Calcd for C22H19F3N3O2[M+H]+414.1429，found 414.1424。
Example five: antibacterial activity determination of beta-carboline amide compounds containing beta-arylamine
The in vitro antibacterial activity evaluation is carried out by adopting a plate hypha growth rate inhibition method, and test strains are selected to be activated on a PDA plate, wherein the test strains comprise rice sheath blight bacteria (Rhizoctonia solani), wheat sheath blight bacteria (Rhizoctonia cerealis), Sclerotinia sclerotiorum (Sclerotinia sclerotiorum), wheat gibberellic disease bacteria (Fusarium graminearum), Botrytis cinerea (Botrytis cinerea), Phytophthora capsici (Phytophthora capsici) and rice blast bacteria (Phytophthora cerealis). Preparing PDA drug-containing plates with compound concentration of 50mg/L, preparing a bacterial cake with the diameter of 5mm from a test strain, placing the bacterial cake in the center of a drug-containing culture dish, culturing at constant temperature of 25 ℃ until the test strain in a blank control dish grows to be close to the edge of the culture dish, measuring the bacterial colony diameter of each drug-containing plate by using a cross method, calculating the inhibition rate of the compound on the growth of hyphae, and calculating the inhibition rate of the compound on diseases according to the following formula:
Figure BSA0000185446800000062
the results of the test of the bacteriostatic activity of the beta-carboline-1-amide compound containing beta-arylamine under the concentration condition of 50mg/L are shown in Table 1.
TABLE 1 inhibitory rate of beta-carboline-1-amide compounds containing beta-arylamine against pathogenic bacteria (50mg/L,%)
Figure BSA0000185446800000071
Note: NT indicates that bioassay was not performed
From table 1, it can be seen that the synthesized beta-carboline-1-amide compound containing beta-arylamine shows moderate to excellent bacteriostatic activity on tested pathogenic bacteria, and shows a certain broad spectrum. When the connected amine is phenethylamine, the corresponding beta-carboline-1-amide compounds have excellent inhibition effect on botrytis cinerea and the like, and are equivalent to positive control fluxapyroxad; the compound 3-3 has a better inhibiting effect on rice sheath blight disease than the fluxapyroxad at a concentration of 50 mg/L.
The use of beta-carboline-1-amides containing beta-arylamine as agricultural fungicides of the present invention has been described by way of specific examples, and those skilled in the art can take the contents of the present invention as a reference, and appropriately modify the raw materials, process conditions, etc. to achieve other objects without departing from the contents of the present invention, and all such similar substitutes and modifications will be apparent to those skilled in the art and are intended to be included within the scope of the present invention.

Claims (6)

1.如下通式(I)所示的含β-芳基胺的β-咔啉酰胺类化合物，及其农药上可以接受的盐，1. The β-carboline amide compounds containing β-arylamine shown in the following general formula (I), and acceptable salts thereof on pesticides,
Figure FSA0000185446790000011
Figure FSA0000185446790000011
 通式(I)中R1，R2，R3，R4，表示取代基：R 1 , R 2 , R 3 , R 4 in the general formula (I) represent substituents: R1表示氢、羟基、甲氧基、1-12碳烷氧基、苄氧基、卤素(氟、氯、溴)；R 1 represents hydrogen, hydroxyl, methoxy, 1-12 carbon alkoxy, benzyloxy, halogen (fluorine, chlorine, bromine); R2表示氢，羟基，甲氧基，1-12碳的烷氧基，1-12碳的烃基；R 2 represents hydrogen, hydroxyl, methoxy, alkoxy of 1-12 carbons, hydrocarbon group of 1-12 carbons; R3表示氢，1-12碳的烃基，羟亚甲基，羧基，羧酸甲酯，羧酸乙酯；R 3 represents hydrogen, hydrocarbon group of 1-12 carbons, hydroxymethylene, carboxyl, methyl carboxylate, ethyl carboxylate; R4表示氢，羟基，甲氧基，1-12碳的烷氧基，苯基，吡啶基，呋喃基，噻吩基；R 4 represents hydrogen, hydroxyl, methoxy, alkoxy of 1-12 carbons, phenyl, pyridyl, furyl, thienyl;
Figure FSA0000185446790000012
表示苯基、1-6碳烃基取代的苯基、卤素取代的苯基、1-6碳烃氧基取代的苯基、脂肪链碳羟基、烷基；吲哚、1-6碳烃基取代的吲哚、卤素取代的吲哚、1-6碳烃氧基取代的吲哚、N-(1-6碳烃基)-吲哚、N-(芳基)-吲哚、N-(芳磺酰基)-吲哚；吡啶、1-5碳烃基取代的吡啶、卤素取代的吡啶、三氟甲基取代的吡啶、1-5碳烃氧基取代的吡啶；噻吩；呋喃；吡唑。
Figure FSA0000185446790000012
Represents phenyl, 1-6 carbon hydrocarbyl substituted phenyl, halogen substituted phenyl, 1-6 carbon hydrocarbyloxy substituted phenyl, aliphatic chain carbon hydroxyl, alkyl; indole, 1-6 carbon hydrocarbyl substituted Indole, halogen substituted indole, 1-6 carbon hydrocarbyloxy substituted indole, N-(1-6 carbon hydrocarbyl)-indole, N-(aryl)-indole, N-(arylsulfonyl )-indole; pyridine, 1-5 carbon hydrocarbyl substituted pyridine, halogen substituted pyridine, trifluoromethyl substituted pyridine, 1-5 carbon hydrocarbyloxy substituted pyridine; thiophene; furan; pyrazole. 2.权利要求1通式(I)所示的化合物，其特征在于，优选自以下两部分化合物：2. The compound represented by the general formula (I) of claim 1, characterized in that it is preferably selected from the following two-part compounds: 第一部分：first part:
Figure FSA0000185446790000013
Figure FSA0000185446790000013
 第二部分：the second part: 其中R1和Ar表示的取代基如第一部分所示，R2、R3、R4表示的取代基如下所示：The substituents represented by R 1 and Ar are shown in the first part, and the substituents represented by R 2 , R 3 and R 4 are shown as follows:
Figure FSA0000185446790000021
Figure FSA0000185446790000021
 3.权利要求1所示的含β-芳基胺的β-咔啉酰胺类化合物在防治农业植物病害上的应用。3. The application of the β-carboline amide compound containing β-arylamine shown in claim 1 in preventing and treating agricultural plant diseases. 4.如权利3所要求的应用，其特征在于，所述的农业病害为油菜菌核病菌、水稻纹枯病菌、草莓灰霉病菌、小麦纹枯病菌、小麦赤霉病菌、小麦全蚀病菌、番茄灰霉病菌、马铃薯晚疫病菌、辣椒疫霉病菌、番茄早疫病菌、水稻恶苗病菌、马铃薯干腐病菌、黄瓜炭疽病菌和水稻稻瘟病菌。4. application as claimed in claim 3, is characterized in that, described agricultural disease is rape sclerotiorum, rice sheath blight, strawberry botrytis cinerea, wheat sheath blight, wheat scab, wheat total erosion Bacteria, tomato botrytis cinerea, potato late blight, pepper phytophthora, tomato early blight, rice baica, potato dry rot, cucumber anthracnose and rice blast. 5.根据权利3和4的用途，所述化合物加工成乳油、水乳剂、微乳剂、可湿性粉剂、水分散粒剂、悬浮剂。5. Use according to claims 3 and 4, wherein the compound is processed into emulsifiable concentrates, aqueous emulsions, microemulsions, wettable powders, water dispersible granules, suspensions. 6.权利要求1和2所述含β-芳基胺的β-咔啉酰胺类化合物在防治植物病害中的应用，其特征在于，它和商品化杀菌剂中的一种或多种组合在制备复配杀菌剂中的用途；商品化杀菌剂选自双炔酰菌胺、氟唑菌酰羟胺、氟吡菌酰胺、嘧菌酯、吡唑醚菌酯、丙硫菌唑、肟菌酯、环菌唑、代森锰锌、氟环唑、戊唑醇、啶酰菌胺、甲霜灵、啶氧菌酯、苯醚甲环唑、丙环唑、百菌清、噻酰菌胺、甲噻诱胺、异噻菌胺、宁南霉素、烯丙异噻唑、氟吗啉、烯酰吗啉。6. the application of the described β-carboline amide compound containing β-arylamine in claim 1 and 2 in preventing and treating plant diseases, it is characterized in that, it is combined with one or more of the commercial fungicides in The use in the preparation of compound fungicides; the commercial fungicides are selected from the group consisting of Dipropamid, Fluoxapyr, Fluopyram, Azoxystrobin, Pyraclostrobin, Prothioconazole, Trioxystrobin , Cycloconazole, Mancozeb, Epoxiconazole, Tebuconazole, Boscalid, Metalaxyl, Picoxystrobin, Difenoconazole, Propiconazole, Chlorothalonil, Tiafenamide , Methiamine, Isothiamid, Ningnamycin, Allylisothiazole, Flumorpholine, Dimethomorph.
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CN113278020A (en) * 2021-06-02 2021-08-20 河北工业大学 Pityriacitrin alkaloid derivative containing acylthiourea structure and preparation method and application thereof
CN113278020B (en) * 2021-06-02 2022-07-12 河北工业大学 Pityriacitrin alkaloid derivative containing acylthiourea structure and its preparation method and use
CN116396291A (en) * 2023-04-10 2023-07-07 南京农业大学 Application of a class of 1-amide and 1-hydrazide substituted β-carboline derivatives as agricultural fungicides
WO2025030709A1 (en) * 2023-08-08 2025-02-13 南京医科大学 Selective monoamine oxidase b inhibitor and pharmaceutical use thereof

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