A quinoline compound and its application in agricultural fungicide

Abstract

The present invention belongs to the technical field of pesticide synthesis, and provides a quinoline compound and its application in agricultural fungicides. The structural formula of the quinoline compound is:. The control target of the compound is Rhizoctonia solani ( Rhizoctonia solani )、Alternaria alternata( Alternaria alternate ) or Pyricularia oryzae ( Pyricularia oryzae ). The compound has excellent commercial application prospects and is suitable for industrial production. The quinoline compound can also be used as a lead compound to further improve the biological activity through structural modification, and serve as an important source for the development of innovative drugs.

Description

Technical Field

[0001] The invention belongs to the technical field of pesticide synthesis and relates to a quinoline compound and a preparation method and application thereof. Background Art

[0002] The disclosure of this background information is intended to enhance understanding of the general background of the invention and should not necessarily be taken as an acknowledgment or any form of suggestion that this information constitutes the prior art already known to a person skilled in the art.

[0003] Plant fungal diseases seriously affect the yield and quality of crops. Pathogenic fungi account for about 70%-80% of plant diseases, and some fungi secrete toxins that are harmful to human health. Tobacco is an important economic crop, and it is easily affected by various fungal diseases during its growth, such as tobacco target spot, brown spot disease, and bacterial wilt. At the same time, rice, as a major food crop, is also threatened by a variety of fungi, causing serious economic losses to crops.

[0004] At present, the use of chemical fungicides is still the most effective and economical way to prevent and control fungal diseases. However, long-term and large-scale use has led to increasing problems such as residual agents, resistance and non-target biological toxicity. There is an urgent need to develop new efficient and safe fungicides. Natural products have novel structures, unique mechanisms of action and are environmentally friendly. Using them as lead compounds to develop new pesticides has become an important source for drug development.

[0005] Quinoline alkaloids are an important class of nitrogen-containing heterocyclic natural products. Due to their diverse structural characteristics, they have a variety of biological and pharmacological activities, such as anti-malarial, anti-inflammatory, anti-cancer and antibacterial. Therefore, quinoline compounds play an important role in drug research and are widely used in the development of active molecules. In recent years, this type of compound has also shown outstanding potential in the agricultural field. For example, tetrahydroquinoline alkaloids have anti-plant pathogenic fungi, insecticides and antiviral activities. Therefore, the development of quinoline derivatives is expected to provide novel lead compounds for the prevention and treatment of plant fungal diseases. Summary of the invention

[0006] In order to further develop agents for preventing and treating plant fungal diseases, the present invention provides a quinoline compound having good biological activity against major pathogenic fungi of tobacco and rice.

[0007] Another object of the present invention is to provide a method for synthesizing the above quinoline compounds, which has short synthesis steps and has industrial prospects.

[0008] Another object of the present invention is to provide a use of the above-mentioned quinoline compound in the preparation of agricultural fungicides.

[0009] To achieve the above purpose, the present invention adopts the following technical solution.

[0010] A quinoline compound, referred to as BDPQ5, has the structural formula:

[0011] .

[0012] A method for preparing the above-mentioned quinoline compound comprises the following steps:

[0013] (1) and benzyl bromide in the presence of NaH in an organic solvent, and after the reaction is completed, separation and purification are obtained: ;

[0014] (2) The product is reacted with phenylhydrazine in the presence of acetic acid, and the target product is obtained by separation and purification after the reaction is completed.

[0015] In steps (1) and (2), the reaction temperature is 80°C.

[0016] In step (1), the separation and purification step is as follows: after the reaction solution is acidified, the solvent is removed and then dichloromethane (DCM) is added for extraction, saturated NaHCO3 is added to the organic layer for washing, and the organic layer is removed from the solvent and then passed through a chromatography column, wherein the chromatography column uses methanol: dichloromethane (MeOH: DCM) in a volume ratio of 1:20 as the mobile phase.

[0017] In step (2), the separation and purification step is as follows: after removing the solvent from the reaction solution, dilute acid is added, followed by extraction with dichloromethane (DCM), the organic layer is washed with saturated NaHCO3, the organic layer is removed from the solvent and then passed through a chromatography column, wherein the chromatography column uses methanol: dichloromethane (MeOH: DCM) in a volume ratio of 1:20 as the mobile phase.

[0018] The synthesis comprises the following steps:

[0019] (a) 3,4-(methylenedioxy)acetophenone and diethyl carbonate react in an organic solvent in the presence of NaH, and after the reaction, separate and purify to obtain: ;

[0020] (b) and triethyl orthoformate in the presence of acetic anhydride, and separated and purified to obtain ;

[0021] (c) and 3,4-(methylenedioxy)aniline in an organic solvent, and after the reaction is completed, the product is separated and purified to obtain: ;

[0022] (d) and diphenyl ether, and after the reaction is completed, the desired product is obtained by separation and purification.

[0023] In step (a), the reaction temperature is 70°C.

[0024] In step (a), the separation and purification step is as follows: the reaction solution is acidified and then water is added, followed by extraction with ethyl acetate, the organic layer is extracted with a saturated NaCl solution, the organic layer is dried with anhydrous Na2SO4, and the solvent is removed to obtain the product.

[0025] In step (b), the reaction temperature is 140°C.

[0026] In step (b), the separation and purification step is as follows: water is added to the reaction solution, and then extracted with ethyl acetate, the organic layer is dried over anhydrous Na2SO4, and then silica gel column chromatography is performed with a mobile phase of petroleum ether:ethyl acetate in a volume ratio of 3:1, and the solvent is removed to obtain the product.

[0027] In step (c), the separation and purification step is as follows: after the reaction system is separated into solid and liquid, the solid is washed with ethanol, and then silica gel column chromatography is performed with a mobile phase of petroleum ether:ethyl acetate in a volume ratio of 3:1 to remove the solvent to obtain the product.

[0028] In step (d), the reaction temperature is 260°C.

[0029] In step (d), the separation and purification step is: adding petroleum ether to the reaction solution, then separating the solid and the liquid, and washing the solid with ethyl acetate.

[0030] The present invention also provides a use of the quinoline compound as an agricultural fungicide.

[0031] The present invention also provides a bactericidal composition comprising the above-mentioned quinoline compound. The quinoline compound is used as an effective ingredient in the bactericidal composition, and its content is 0.1 wt%-99 wt%; preferably, the content is 1-80 wt%. More preferably, the content is 5-50 wt%.

[0032] The control target of the agricultural fungicide or fungicide composition is Rhizoctonia solani ( Rhizoctonia solani )、Alternaria alternata( Alternaria alternate ) or Pyricularia oryzae ( Pyricularia oryzae The control target of the agricultural fungicide or fungicide composition can also be the sexual generation of the above microorganisms, Rhizoctonia solani ( Rhizoctonia solani ) The sexual generation is the melon fungus ( Thanatephorus cucumeris ), Pyricularia oryzae ( Pyricularia oryzae )'s sexual generation is Magnaporthe oryzae .

[0033] The crops controlled by the agricultural fungicide or fungicide composition are selected from tobacco or rice.

[0034] The fungicidal composition may further comprise other inert ingredients for stabilizing the active ingredients and facilitating their application to crops or attachment to targets, such as fillers, wetting agents, dispersants, defoamers, antifreeze agents, solvents, emulsifiers, preservatives, disintegrants, pigments, etc.

[0035] The above composition can be processed by the common methods in the prior art, and the preferred dosage forms include suspensions, granules, wettable powders, water-dispersible granules, emulsifiable concentrates, aqueous emulsions, and microemulsions.

[0036] The endpoints and any values ​​of the ranges disclosed in this application are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of each range, the endpoint values ​​of each range and the individual point values, and the individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be regarded as specifically disclosed in this application.

[0037] The present invention has the following advantages:

[0038] The quinoline compounds provided by the present invention can inhibit the mycelial growth of tobacco target spot pathogen, tobacco brown spot pathogen, rice sheath blight pathogen and rice blast pathogen at a relatively low concentration, and in particular, the antibacterial activity against rice blast pathogen and tobacco brown spot pathogen is better than that of major commercialized agents such as kasugamycin, trifloxystrobin and syringystrobin, and can be used to prepare the above-mentioned control agents for several diseases, with excellent commercial application prospects. The quinoline compounds provided by the present invention have short synthesis steps and simple purification, and are suitable for industrial production. The quinoline compounds provided by the present invention can also be used as lead compounds, and the biological activity can be further improved through structural modification, as an important source for the development of innovative drugs. BRIEF DESCRIPTION OF THE DRAWINGS

[0039] Figure 1 Quinoline compound BDPQ5 1 H NMR spectrum;

[0040] Figure 2 Quinoline compound BDPQ5 13 C NMR spectrum;

[0041] Figure 3 This is the HRMS spectrum of the quinoline compound BDPQ5. DETAILED DESCRIPTION

[0042] The present invention will be further described below in conjunction with examples, but the present invention is not limited by the following examples.

[0043] Example 1 Preparation of quinoline compounds

[0044] (1) Synthesis of 1a

[0045]

[0046] Take a centrifuge tube and add dry THF (15 mL), add 3,4-(methylenedioxy)acetophenone (S0, 30 mmol), and stir and dissolve at 0 °C to obtain S0 solution;

[0047] Take another clean 100 mL flask and add NaH (60% mineral oil, 4.8 g, 120 mmol), anhydrous THF (25 mL), and diethyl carbonate (19.4 mL, 120 mmol) in sequence;

[0048] Under nitrogen protection, the S0 solution was slowly added dropwise to the above flask, and the mixture was heated to reflux at 70 °C for reaction. The reaction progress was monitored by thin layer chromatography (TLC) using petroleum ether:ethyl acetate (PE:EA=1:5, v / v) as the developing solvent. After reflux for 6 h, 1 mol / L HCl (30 mL) was added to the reaction mixture to remove excess NaH and terminate the reaction.

[0049] Water (20 mL) was added to the above system, and the mixture was extracted with ethyl acetate for three times, 20 mL each time. The organic layer was then extracted with saturated NaCl solution. The organic layer was dried over Na2SO4, and the solvent was dried by rotary evaporation at 48 °C and pumped dry with an oil pump to obtain a yellow-brown oil 1a with a yield of 72.2%.

[0050] (2) Synthesis of 2a

[0051]

[0052] Take a 50ml round-bottom flask, add intermediate 1a (5.1 g, 21.6 mmol), CH(OEt)3 (18 mL, 108 mmol), Ac2O (11 mL, 108 mmol), and reflux at 140 °C for 16 h. Add 25 mL of water to the reactant, extract with EA, dry the organic layer with anhydrous Na2SO4, and then purify by column chromatography (PE: EA=3: 1, v / v) to obtain intermediate 2a with a yield of 62.9%.

[0053] (3) Synthesis of 3a

[0054]

[0055] Take a 50 mL round-bottom flask, add the intermediate product 2a (4.0 g, 13.59 mmol), add 25 mL isopropanol, and then add 3,4-(methylenedioxy)aniline (1.12 g, 8.15 mmol). After reacting at 40°C for half an hour, the reaction progress was monitored by TLC (EA: PE=2: 1, v / v). The reaction was complete after 4 hours. The reaction system was filtered under reduced pressure, the filter cake was washed with ethanol, pumped dry, and purified by column chromatography (PE: EA=3: 1, v / v) to obtain a white precipitate 3a with a yield of 47.8%.

[0056] (4) Synthesis of 4a

[0057]

[0058] 5 10 mL high temperature reaction tubes were added to each reaction tube, 5 mL of diphenyl ether was added, and the intermediate product 3a (0.3 g) was added, and the reaction was refluxed at 260 °C. The reaction progress was monitored by TLC petroleum ether: ethyl acetate (PE: EA=1: 5, v / v). The reaction was completed after 5 h. PE was added to the reaction system for extraction 3 times, 20 mL each time, and a black solid was precipitated. The solid was filtered and washed with ethyl acetate to obtain a black solid 4a with a yield of 63.9%.

[0059] (5) Synthesis of 5a

[0060]

[0061] Take a 50 mL round-bottom flask and add the intermediate product 4a (300 mg), NaH (42.73 mg, 1.07 mmol), DMF (20 mL), benzyl bromide (105 μL, 0.88 mol), and reflux at 80 °C for 8 h. Methanol: dichloromethane (MeOH: DCM=1: 10, v / v) was used as the developing solvent and TLC monitored the reaction progress; after 8 h, the reaction was complete, 1 mol / L HCl (30 mL) was added to remove NaH, the reaction solution was dried by rotary evaporator, DCM (20 mL) was added for extraction, the organic layer was washed with NaHCO3, the organic layer was dried and then passed through a chromatography column (MeOH: DCM=1: 20, v / v) to obtain a brown solid 5a with a yield of 60.5%.

[0062] (6) Synthesis of BDPQ5

[0063]

[0064] Compound 5a (200 mg) was added to a high temperature reaction tube, followed by 5 mL of acetic acid and 31.9 μL of phenylhydrazine. The reaction was refluxed at 80 °C and monitored by TLC (MeOH: DCM=1:10, v / v). The reaction was complete after 8 h. The reaction solution was dried by spin drying, and 1 mol / L HCl (30 mL) was added to remove phenylhydrazine. DCM (20 mL) was added for extraction. The organic layer was washed with NaHCO3, and the organic layer was dried by spin drying and then subjected to column chromatography (MeOH: DCM=1:20, v / v) to obtain a yellow solid BDPQ5, i.e., the target compound, with a yield of 63.0%. 1 HNMR, 13 C NMR and HRMS spectra are shown in Figures 1-3 As shown, the analysis is as follows: 1 H NMR (600 MHz, DMSO-d6) δ 10.39(s, 1H), 7.88 (s, 1H), 7.84 (dd, J = 7.8, 1.9 Hz, 2H), 7.81 (dd, J = 7.6, 2.6Hz, 2H), 7.76 - 7.72 (m, 2H), 7.41 - 7.34 (m, 5H), 7.22 (d, J = 7.9 Hz, 1H), 6.68 (s, 1H), 6.36 (s, 2H), 6.30 (s, 2H), 6.20 (s, 2H). 13 C NMR (151 MHz, DMSO)δ 172.50, 153.00, 149.66, 149.53, 149.46, 148.69, 146.03, 141.80, 139.06,134.78, 133.58, 131.68, 130.88, 129.42, 128.90, 127.93, 127.20, 123.60,123.31, 114.31, 112.73, 109.65, 108.53, 104.87, 102.29, 99.81, 99.59, 60.63,40.48, 21.55. HRMS (ESI) for C 31 H 22 O4N3 + [M] + , calculated 500.1605, found500.1480. From the above, we can know that the structural formula of BDPQ5 is: .

[0065] Example 2 Indoor toxicity of quinoline compounds against pathogens

[0066] The mycelium growth rate method was used to determine the indoor toxicity of the quinoline derivative BDPQ5 to the main pathogenic fungi of tobacco and rice. The specific process is as follows:

[0067] (1) Isolation of pathogenic strains

[0068] The diseased leaves with obvious symptoms of the pathogen were collected from the main tobacco and rice producing areas in Jiangxi Province, and the strain was isolated and purified by the water agar method. After purification for 5 times, the tobacco target spot pathogen ( Rhizoctonia solani )、Tobacco brown spot pathogen ( Alternaria alternate )、Rhizoctonia solani( Rhizoctonia solani ) and rice blast fungus ( Pyricularia oryzae ) 4 pathogens for subsequent indoor virulence testing of compounds.

[0069] (2) Preparation of drug-containing culture medium

[0070] The quinoline derivative BDPQ5 was accurately weighed and dissolved in DMSO solution to prepare a mother solution, which was then diluted to the target concentration with a 0.1% Tween-80 aqueous solution. The diluent and the sterilized PDA medium were shaken at a volume ratio of 1:9 (drug solution: medium) to prepare a drug-containing medium with a target concentration of 20 μg / mL. The blank control was added with the same volume of 0.1% Tween-80. The commercial drugs kasugamycin (6% wettable powder), trifloxystrobin (40% suspension) and syringoxystrobin (20% suspension) were directly diluted to the target concentration with a 0.1% Tween-80 aqueous solution.

[0071] (3) Toxicity assay

[0072] The toxicity was determined by the hyphae growth rate method. The test bacteria were inoculated on PDA plates for pre-culture for 5 days. A 5 mm diameter puncher was used to punch a bacterial cake at 1 / 3 of the edge of the colony. The bacterial cake was then transferred to the drug-containing and blank PDA culture media, respectively, and cultured in a constant temperature incubator at 28°C for 3 days. Each treatment was repeated 3 times. When the hyphae of the blank control filled 2 / 3 of the culture medium, the colony diameter was measured by the cross method, and the average value was calculated. Compared with the control, the antibacterial rate of the compound on the hyphae was calculated according to the following formula:

[0073] .

[0074] Table 1 Results of indoor toxicity test of quinoline derivative BDPQ5 against four pathogenic fungi

[0075]

[0076] The results in Table 1 show that compound BDPQ5 exhibits good inhibitory effects on a variety of plant pathogenic fungi such as tobacco target spot, tobacco brown spot and rice blast, and has a broad-spectrum antifungal activity. At the same concentration, the inhibitory activity of compound BDPQ5 on tobacco target spot is comparable to that of commercial agents kasugamycin and syringostyrin. The inhibitory effect of compound BDPQ5 on tobacco brown spot is better than that of three commercial agents (kasugamycin, trifloxystrobin and syringostyrin). The inhibitory activity of compound BDPQ5 on rice sheath blight is better than that of trifloxystrobin and comparable to that of kasugamycin and syringostyrin. The inhibitory effect of compound BDPQ5 on rice blast is better than that of the above three commercial agents. In summary, quinoline compound BDPQ5 has high application potential and development value.

[0077] Example 3 Preparation of BDPQ5 formulation

[0078] 1. Suspension

[0079] BDPQ5 technical 5%-50%, dispersant 2%-5%, wetting agent 1%-3%, thickener 0.05%-1%, defoamer 0.1%-0.3%, antifreeze 1%-3%, preservative 0.1%-0.5%, water to 100%;

[0080] The dispersant is selected from polycarboxylates, methyl acrylates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, and polyvinyl pyrrolidone;

[0081] The wetting agent is selected from fatty alcohol block polyether, polyoxyethylene sorbitan fatty acid ester, sorbitan fatty acid ester;

[0082] The thickener is selected from magnesium aluminum silicate, xanthan gum, and white carbon black;

[0083] The defoaming agent is selected from silicone;

[0084] The antifreeze agent is selected from polyols, such as ethylene glycol, propylene glycol, and glycerol;

[0085] The preservative is selected from isothiazolinones and sodium benzoate.

[0086] For example, the raw materials can be weighed according to the following formula:

[0087] BDPQ5 technical 10%; carboxylates and lignin sulfonates are used as dispersants, with dosages of 3% and 2% respectively; EO / PO block copolymer is used as wetting agent, 1.5%; magnesium aluminum silicate and xanthan gum are used as thickeners, with dosages of 0.5% and 0.05% respectively; organosilicon complex, GY-X60, is used as defoaming agent, 0.15%; ethylene glycol is used as antifreeze agent, 3%; kason is used as preservative, 0.1%; water is the balance.

[0088] The raw materials are placed in a reactor in sequence according to the formula ratio, mixed evenly, and then subjected to high-speed shearing, wet grinding, and finally homogenized filtration to obtain the product. The main equipment includes a batching kettle, a sand mill, etc.

[0089] Main technical indicators of suspension concentrate: suspension rate not less than 90%, pH 4-8, persistent foaming not more than 50 mL (after 1 min), 75 μm wet sieve pass rate not less than 98%, pourability, cold storage stability and hot storage stability measured according to GB / T 37137, GB / T 19136 and GB / T 19137 methods are qualified.

[0090] 2. Wettable powder

[0091] BDPQ5 technical 1%-90%, dispersant 3%-15%, wetting agent 2%-10%, filler to 100%;

[0092] The dispersant is selected from carboxylates, alkylnaphthalene sulfonate polycondensates, such as one or more combinations of GY-D800, Dispersol PSR 19, and Dispersol BB4;

[0093] The wetting agent is selected from anionic wetting agents, such as one or a combination of GY-WS01 and Multiwet 8269;

[0094] The filler is selected from kaolin, corn starch or a combination thereof.

[0095] The above substances are mixed evenly according to the formula ratio, and then mixed after air flow crushing to obtain wettable powder. The main equipment includes a mixer, an air flow crusher, etc.

[0096] Main technical indicators of wettable powder: suspension rate not less than 75%, wetting time not more than 120 s, 45 μm wet sieve pass rate not less than 95%, moisture content not more than 3%, pH 4-9, and thermal storage stability measured according to GB / T 19137 method is qualified.

[0097] 3. Water dispersible granules

[0098] BDPQ5 technical material 1%-80%, dispersant 3%-12%, wetting agent 1%-10%, disintegrant 1%-10%, binder 0%-8%, filler to 100%;

[0099] The dispersant is selected from carboxylates, lignin sulfonates, alkylnaphthalene sulfonate polycondensates, such as GY-D800, Dispersol PSR 19, DM04. The wetting agent is selected from polycarboxylates, anions, such as sodium dodecyl sulfonate, alkylnaphthalene sulfonate formaldehyde condensates, or one or more combinations thereof;

[0100] The disintegrant is selected from urea, inorganic salts, sucrose, such as one or more combinations of wgwin D909S, sucrose, ammonium sulfate, and urea;

[0101] The binder is selected from one or more combinations of polyethylene glycol 6000, modified polyvinyl alcohol, and carboxymethyl cellulose;

[0102] The filler is selected from corn starch or diatomaceous earth.

[0103] The above materials are mixed evenly according to the formula ratio, and then mixed to obtain coarse powder after air flow crushing, and then added with appropriate amount of water for kneading and granulation. The main equipment includes mixer, air flow crusher, granulator, dryer, etc.

[0104] Main technical indicators of water dispersible granules: suspension rate not less than 80%, dispersibility not less than 80%, wetting time not more than 90 s, 75 μm wet sieve pass rate not less than 98%, persistent foaming not more than 60 mL (after 1 min), pH 4-9, and hot storage stability measured according to GB / T19137 method is qualified.

[0105] 4. EC

[0106] BDPQ5 technical 20%-50%, emulsifier 1%-10%, solvent to 100%;

[0107] The emulsifier is selected from one or more combinations of Nongru 500#, Nongru 400#, Nongru 600#, and Atlox 4838B;

[0108] The solvent is selected from solvent oil S150, mineral oil or a combination thereof;

[0109] Dissolve the original drug and emulsifier in the solvent, mix them according to the formula, let them stand and filter. The main equipment is a stirring tank.

[0110] Main technical indicators of emulsifiable concentrate: water content not more than 2%, persistent foaming not more than 60 mL (after 1 min), pH 4-8, 200-fold diluted emulsion stability, cold storage stability and hot storage stability measured according to GB / T 1603, GB / T 19136 and GB / T 19137 methods are qualified.

[0111] 5. Microemulsion

[0112] BDPQ5 technical 0.5%-60%, emulsifier 3%-20%, solvent 1%-30%, cosolvent 0%-5%, water to 100%;

[0113] The emulsifier is selected from anionic phosphate esters, such as Atplus 310;

[0114] The solvent is selected from one or more combinations of xylene, cyclohexanone and dimethylformamide;

[0115] The co-solvent is selected from n-butanol or n-pentanol.

[0116] Mix the above substances evenly according to the formula ratio, stir until completely dissolved, add water and stir with a high-speed shear emulsifier until clear and transparent.

[0117] Main technical indicators of microemulsion: qualified transparent temperature range (0-50℃), persistent foaming not more than 30 mL (after 1min), pH 4-8, qualified 200-fold diluted emulsion stability, cold storage stability and hot storage stability measured according to GB / T 1603, GB / T 19136 and GB / T 19137 methods.

Claims

1. A quinoline compound having the structural formula: 。 2. A method for preparing a quinoline compound as claimed in claim 1, characterized in that: The following steps are involved: (1) and benzyl bromide in the presence of NaH in an organic solvent, and after the reaction is completed, separation and purification are obtained: ; (2) The product is reacted with phenylhydrazine in the presence of acetic acid, and the target product is obtained by separation and purification after the reaction is completed.

3. The preparation method according to claim 2, characterized in that: In steps (1) and (2), the reaction temperature is 80°C; In step (1), the separation and purification step is as follows: after the reaction solution is acidified, the solvent is removed and then dichloromethane is added for extraction, the organic layer is washed with saturated NaHCO3, the organic layer is removed and then passed through a chromatography column, and the chromatography column uses methanol:dichloromethane in a volume ratio of 1:20 as the mobile phase; In step (2), the separation and purification step is as follows: after removing the solvent from the reaction solution, dilute acid is added, followed by extraction with dichloromethane, the organic layer is washed with saturated NaHCO3, the organic layer is removed from the solvent and then passed through a chromatography column, wherein the chromatography column uses methanol:dichloromethane in a volume ratio of 1:20 as the mobile phase.

4. Use of the quinoline compound as claimed in claim 1 as an agricultural fungicide.

5. A fungicidal composition comprising the quinoline compound according to claim 1.

6. The bactericidal composition according to claim 5, characterized in that The quinoline compound is used as an effective ingredient in the bactericidal composition, and its content is 0.1 wt%-99 wt%.

7. The bactericidal composition according to claim 5, characterized in that The quinoline compound is used as an effective ingredient in the bactericidal composition, and its content is 1 wt%-80 wt%.

8. The bactericidal composition according to claim 5, characterized in that The quinoline compound is used as an effective ingredient in the bactericidal composition, and its content is 5 wt%-50 wt%.

9. The use according to claim 4 or the bactericidal composition according to claim 5, characterized in that: The control target of the agricultural fungicide or fungicide composition is Rhizoctonia solani ( Rhizoctonia solani )、Alternaria alternata( Alternaria )、Pyricularia oryzae( Pyricularia oryzae ).

10. The use according to claim 4 or the bactericidal composition according to claim 5, characterized in that: The crops controlled by the agricultural fungicide or fungicide composition are selected from tobacco or rice.

11. The bactericidal composition according to claim 5, characterized in that The bactericidal composition further comprises other inert ingredients, which are selected from fillers, wetting agents, dispersants, defoamers, antifreeze agents, solvents, emulsifiers, preservatives, disintegrants or pigments.

12. The bactericidal composition according to claim 5, characterized in that The dosage form of the fungicide composition is selected from suspension, granules, wettable powder, water dispersible granules, emulsifiable concentrate, aqueous emulsion or microemulsion.

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