Agricultural sterilization composition containing quinoline compounds

Abstract

The present invention belongs to the technical field of agricultural pathogen control and provides an agricultural fungicidal composition containing a quinoline compound. The quinoline compound #imgabs0# provided herein can be used alone or in combination with pyraclostrobin to control fungal diseases of tobacco and rice, exhibiting a synergistic effect when used together. The quinoline compound provided herein has excellent commercial application prospects. Compositions containing this compound can synergistically enhance efficacy, reduce the amount of pesticide used, improve control effectiveness, and delay the development of drug resistance.

Description

Technical Field

[0001] The invention belongs to the technical field of agricultural pathogenic microorganism prevention and control, and relates to an agricultural bactericidal composition containing quinoline compounds. 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 regarded 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 pathogenic fungi are a class of pathogens that cause serious damage to plants. They infect and damage plant tissues, causing disease and even death. They can also produce toxins, posing a threat to human and animal health. Therefore, effective prevention and control of plant fungal diseases is crucial for ensuring crop yield and quality, maintaining ecological balance, and safeguarding human health.

[0004] Currently, chemical fungicides remain the most effective and economical way to control fungal diseases. However, long-term, extensive use is increasingly associated with problems such as residues, resistance, and non-target toxicity. The risk of resistance to pesticides used against major pests and diseases of grain and cash crops is increasing due to long-term, continuous, and overuse. Therefore, developing combination pesticides to mitigate the risk of resistance in existing pesticides is an important approach to effectively extend their useful life and delay the development of resistance.

[0005] Quinoline compounds, a class of nitrogen-containing heterocyclic natural products, exhibit excellent pharmacological activities such as antiviral, antifungal, antiparasitic, and anticancer properties due to their diverse structural frameworks. They have been widely used in the development of lead active molecules in medicinal chemistry and agricultural chemistry. In recent years, this class of compounds has also shown significant potential in the agricultural sector. For example, tetrahydroquinoline alkaloids exhibit anti-plant pathogenic fungal, insecticidal, and antiviral activities. Summary of the Invention

[0006] In order to further develop agents for preventing and controlling plant fungal diseases and reduce the drug resistance of existing agents, the present invention provides an agricultural fungicidal composition containing quinoline compounds, which has 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-mentioned quinoline compounds, which has a short synthesis process 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 objectives, the present invention adopts the following technical solutions.

[0010] A quinoline compound, referred to as MDPq5, has the structural formula:

[0011] .

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

[0013] (1) and methyl 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, the organic layer is washed with saturated NaHCO3 solution, the organic layer is removed and then passed through a chromatography column, and the chromatography column uses methanol:dichloromethane (MeOH:DCM) with 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, and then dichloromethane (DCM) is added for extraction, the organic layer is washed with saturated NaHCO3 solution, and after removing the solvent from the organic layer, the organic layer is passed through a chromatography column, and the chromatography column uses methanol:dichloromethane (MeOH:DCM) with 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 with oxygen removed. After the reaction, separation and purification are performed 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 target 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 steps are as follows: the reaction solution is acidified, water is added, and then extracted with ethyl acetate, the organic layer is extracted with saturated NaCl solution, the organic layer is dried with 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, followed by extraction with ethyl acetate, the organic layer is dried over anhydrous Na2SO4, and then silica gel column chromatography is performed using petroleum ether:ethyl acetate in a volume ratio of 3:1 as the mobile phase to remove the solvent to obtain the product.

[0027] In step (c), the separation and purification step is as follows: after solid-liquid separation of the reaction system, the solid is washed with ethanol, and then subjected to silica gel column chromatography using petroleum ether:ethyl acetate in a volume ratio of 3:1 as the mobile phase 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 as follows: petroleum ether is added to the reaction solution, followed by solid-liquid separation, and the solid is washed 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 fungicide composition comprising the aforementioned quinoline compound. The quinoline compound is present as an active ingredient in the fungicide composition in an amount of 0.1 wt% to 99 wt%; preferably, 1 to 80 wt%; and more preferably, 5 to 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-destroying 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, defoaming agents, antifreeze agents, solvents, emulsifiers, preservatives, disintegrants, pigments, and the like.

[0035] To enhance efficacy or expand the antibacterial spectrum, the fungicide composition further comprises other active ingredients. The active ingredient is a fungicide; preferably, the active ingredient is a methoxyacrylate fungicide, such as trifloxystrobin, pyraclostrobin, azoxystrobin, picoxystrobin, or enoxastrobin; these fungicides and the quinoline compound MDPq5 can enhance efficacy within specific ratios; more preferably, the active ingredient is pyraclostrobin.

[0036] The active ingredients of the bactericidal composition are quinoline compound MDPq5 and pyraclostrobin, and the mass ratio of the two is 1:1-9:1; preferably, the mass ratio of the two is 8:2-9:1.

[0037] The above composition can be processed by the methods commonly used in the prior art. Preferred dosage forms include suspensions, granules, wettable powders, water-dispersible granules, emulsifiable concentrates, aqueous emulsions, and microemulsions.

[0038] The endpoints of the ranges and any values ​​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 endpoints of each range, the endpoints of each range and individual point values, and the individual point values ​​can be combined with each other to obtain one or more new numerical ranges, and these numerical ranges should be considered to be specifically disclosed in this application.

[0039] The present invention has the following advantages:

[0040] The quinoline compound MDPq5 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 relatively low concentrations, outperforming the commercial agent carbendazim. It can be used to prepare pesticides for the control of these diseases and has excellent commercial application prospects. The quinoline compound provided by the present invention can also serve as a lead compound, further enhancing its biological activity through structural modification, and serve as an important source for drug development. The quinoline compound MDPq5 provided by the present invention can be synergistically compounded with pyraclostrobin to reduce the dosage of the pesticide, improve the control effect, and delay the development of drug resistance. BRIEF DESCRIPTION OF THE DRAWINGS

[0041] Figure 1 For quinoline compound MDPq5 1 H NMR spectrum;

[0042] Figure 2For quinoline compound MDPq5 13 C NMR spectrum;

[0043] Figure 3 This is the HRMS spectrum of the quinoline compound MDPq5. DETAILED DESCRIPTION

[0044] The present invention will be further described below with reference to the examples, but the present invention is not limited by the following examples.

[0045] Example 1 Preparation of quinoline compounds

[0046] (1) Synthesis of 1a

[0047]

[0048] 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;

[0049] In another clean 100 mL flask, add NaH (60% in mineral oil, 4.8 g, 120 mmol), anhydrous THF (25 mL), and diethyl carbonate (19.4 mL, 120 mmol) in sequence;

[0050] Under nitrogen, the SO solution was slowly added dropwise to the flask and heated under reflux at 70°C. 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.

[0051] Water (20 mL) was added to the above system, and the mixture was extracted with ethyl acetate three times (20 mL each time). The organic layer was then extracted with saturated NaCl solution. The organic layer was dried over anhydrous Na2SO4, and the solvent was dried on a rotary evaporator at 48°C and pumped dry with an oil pump to obtain a yellow-brown oil 1a in a yield of 72.2%.

[0052] (2) Synthesis of 2a

[0053]

[0054] To a 50 mL round-bottom flask, intermediate 1a (5.1 g, 21.6 mmol), CH(OEt)₃ (18 mL, 108 mmol), and Ac₂O (11 mL, 108 mmol) were added and refluxed at 140°C for 16 h. The reaction mixture was then added with 25 mL of water and extracted with EA. The organic layer was dried over anhydrous Na₂SO₄ and purified by column chromatography (PE:EA = 3:1, v / v) to afford intermediate 2a in a 62.9% yield.

[0055] (3) Synthesis of 3a

[0056]

[0057] A 50 mL round-bottom flask was charged with intermediate 2a (4.0 g, 13.59 mmol), 25 mL of isopropanol, and 3,4-(methylenedioxy)aniline (1.12 g, 8.15 mmol). The reaction was incubated at 40°C for half an hour. TLC was used to monitor the reaction progress (EA:PE = 2:1, v / v). The reaction was complete after 4 hours. The reaction mixture was filtered under reduced pressure, and the filter cake was rinsed with ethanol, pumped dry, and purified by column chromatography (PE:EA = 3:1, v / v) to afford a white precipitate 3a in 47.8% yield.

[0058] (4) Synthesis of 4a

[0059]

[0060] Five 10 mL high-temperature reaction tubes were added to each tube, along with 5 mL of diphenyl ether and 0.3 g of intermediate 3a. The reaction was refluxed at 260°C. The reaction progress was monitored by TLC using petroleum ether:ethyl acetate (PE:EA = 1:5, v / v). The reaction was complete after 5 h. PE was added to the reaction system for extraction three times, 20 mL each time, to precipitate a black solid. The solid was filtered and washed with ethyl acetate to obtain 4a as a black solid in a 63.9% yield.

[0061] (5) Synthesis of 5a

[0062]

[0063] A 50 mL round-bottom flask was charged with intermediate 4a (300 mg), NaH (42.73 mg, 1.07 mmol), DMF (20 mL), and BrCH3 (105 μL, 1.91 mol). The mixture was refluxed at 80°C for 8 h. TLC monitoring of the reaction progress was performed using methanol:dichloromethane (MeOH:DCM = 1:10, v / v). After 8 h, the reaction was complete. The NaH was removed by adding 1 mol / L HCl (30 mL). The reaction solution was then dried on a rotary evaporator and extracted with DCM (20 mL). The organic layer was washed with saturated NaHCO3 solution, dried, and then purified by chromatography (MeOH:DCM = 1:20, v / v) to afford 5a as a brown solid in a 49.4% yield.

[0064] (6) Synthesis of MDPq5

[0065]

[0066] The intermediate product 5a (200 mg) was added to a high-temperature reaction tube, along with 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 spin-dried and the phenylhydrazine was removed by adding 1 mol / L HCl (30 mL). The mixture was then extracted with DCM (20 mL). The organic layer was washed with saturated NaHCO3 solution, spin-dried, and then column chromatography (MeOH:DCM=1:20, v / v) was performed to obtain MDPq5 as a yellow solid, the target compound, in a yield of 58.0%. 1 HNMR (600 MHz, DMSO-d6) δ 10.39 (s, 1H), 8.05 - 7.99 (m, 1H), 7.73 (d, J = 7.6Hz, 3H), 7.66 - 7.62 (m, 3H), 7.59 (s, 1H), 7.16 (d, J = 8.1 Hz, 1H), 6.94 (s, 1H), 4.85 (s, 3H). 13C NMR (151 MHz, DMSO) δ 153.07, 149.62, 149.49,149.13, 148.72, 145.67, 141.42, 139.06, 134.59, 131.66, 130.89, 127.91,123.64, 123.11, 113.74, 111.92, 109.67, 108.44, 104.84, 102.29, 99.74, 99.34,55.39, 46.38, 40.53. HRMS (ESI) for C 25 H 18 O4N3 + [M] + , calculated 424.1292, found 424.1194. From the above, we can see that the structural formula of MDPq5 is: .

[0067] Example 2 Indoor Toxicity of Quinoline Compound MDPq5 to Pathogens

[0068] The mycelial growth rate method was used to determine the indoor toxicity of the quinoline derivative MDPq5 against major tobacco and rice pathogenic fungi. The specific process is as follows:

[0069] (1) Isolation of pathogenic strains

[0070] Diseased leaves with obvious pathological characteristics of the pathogen were collected from the main tobacco and rice producing areas in Jiangxi Province and the strain was isolated and purified using the water agar method. After purification for 5 times, the tobacco target spot pathogen ( Rhizoctonia solani )、Tobacco brown spot pathogen ( Alternaria alternate ), Rice Sheath Blight Pathogen ( Rhizoctonia solani ) and rice blast fungus ( Pyricularia oryzae ) 4 pathogens for subsequent indoor virulence testing of compounds.

[0071] (2) Preparation of drug-containing culture medium

[0072] Accurately weigh the quinoline derivative MDPq5 and dissolve it in DMSO to prepare a stock solution. The stock solution was then diluted to the target concentration with 0.1% Tween-80 aqueous solution. The dilution and sterilized PDA medium were shaken together at a volume ratio of 1:9 (drug solution: medium) to prepare a drug-containing medium with a target concentration of 20 μg / mL. For a blank control, the same volume of 0.1% Tween-80 was added. The commercial agent carbendazim (80% wettable powder) was directly diluted to the target concentration with 0.1% Tween-80 aqueous solution.

[0073] (3) Toxicity assay

[0074] Virulence was determined using the hyphae growth rate method. The test bacteria were inoculated onto PDA plates and pre-cultured for 5 days. A 5 mm diameter punch was used to punch a bacterial cake at 1 / 3 of the colony edge. The cake was then transferred to drug-containing and blank PDA medium, respectively, and cultured in a 28°C constant temperature incubator for 3 days. Each treatment was repeated three times. When the hyphae of the blank control filled 2 / 3 of the culture medium, the colony diameter was measured using the cross-hatch method. The average value was calculated and compared with the control. The inhibitory rate of the compound against the hyphae was calculated according to the following formula:

[0075] Antibacterial rate (%) = ×100%.

[0076] Table 1 Results of indoor toxicity tests of the quinoline derivative MDPq5 against four pathogenic fungi

[0077]

[0078] The quinoline derivative MDPq5 exhibited excellent inhibitory activity against four pathogenic fungi. At a dose of 20 μg / mL, the inhibition rate against all four fungi exceeded 50%, outperforming the commercial agent carbendazim and demonstrating its potential as a lead compound for further development.

[0079] Example 3 Indoor Joint Toxicity of Quinoline Compound MDPq5 and Pyraclostrobin

[0080] 1. Tobacco target spot disease

[0081] Using the hyphae growth rate method, tobacco target spot pathogens were inoculated on PDA plates for 5 days. A 5 mm diameter punch was then used to punch a bacterial cake at the edge of the colony. The cake was then transferred to a series of plates containing different concentrations of the agent and cultured for 3 days. Each treatment was repeated three times. After 3 days, the colony diameter was measured and the inhibition rate on hyphae was calculated. The EC value of each agent was calculated using SPSS software. 50 Value, establish toxicity regression equation, R 2 、EC 50 The synergistic effect of pyraclostrobin and the quinoline derivative MDPq5 under the combination treatment was determined according to the Wadley method and 95% confidence limits, and the synergistic coefficient SR (synergy ratio) was calculated. SR < 0.5 was antagonistic, SR > 1.5 was synergistic, and SR between 0.5-1.5 was additive.

[0082] Antibacterial rate (%) = ×100%;

[0083] EC 50 (Theory) = ;

[0084] SR= ;

[0085] Among them, a and b represent the proportions of the two drugs in the mixture respectively.

[0086] Table 2 Results of the combined toxicity test of the quinoline derivative MDPq5 and pyraclostrobin against tobacco leaf spot pathogen

[0087]

[0088] The results in Table 2 show that the combination of the quinoline derivative MDPq5 and pyraclostrobin exhibits excellent inhibitory activity against tobacco target leaf spot pathogens. Synergistic effects were observed at combination ratios of 8:2 and 9:1, with the synergistic effect being most pronounced at a ratio of 9:1, with a coefficient of 1.9787. In summary, the combination of the quinoline derivative MDPq5 and pyraclostrobin effectively inhibits the proliferation of tobacco target leaf spot pathogens while mitigating the development of resistance that can occur with either agent alone.

[0089] 2. Rice blast fungus

[0090] The mycelial growth rate method was used to determine the inhibition rate of different agents on mycelium, and the EC value of each agent was calculated using SPSS software. 50 Value, establish toxicity regression equation, R 2 、EC 50 The synergistic effect of pyraclostrobin and the quinoline derivative MDPq5 under the combination treatment was determined according to the Wadley method with 95% confidence limits, and the synergistic ratio (SR) was calculated.

[0091] Table 3 Results of the combined toxicity test of the quinoline derivative MDPq5 and pyraclostrobin against rice blast fungus

[0092]

[0093] The results in Table 3 show that the combination of the quinoline derivative MDPq5 and pyraclostrobin exhibits significant inhibitory activity against the rice blast pathogen. Synergistic effects were observed when the ratios of quinoline derivative MDPq5 to pyraclostrobin were 8:2 and 9:1. The synergistic effect was particularly evident when the ratio was 8:2, with a synergistic coefficient of 3.5852, demonstrating excellent synergistic activity. These results demonstrate that the combination of the quinoline derivative MDPq5 and pyraclostrobin also exhibits significant inhibitory activity against the rice blast pathogen, effectively mitigating the risk of resistance associated with the use of pyraclostrobin alone.

[0094] Example 4 Preparation of MDPq5 and Mixed Preparations

[0095] 1. Suspension

[0096] MDPq5 technical 5%-50%, dispersant 2%-10%, wetting agent 2%-10%, defoamer 0.01%-2%, thickener 0.05%-2%, antifreeze 0%-8%, preservative 0-2%, water to 100%;

[0097] The dispersant is selected from one or more combinations of carboxylates, lignin sulfonates, and naphthalene sulfonates;

[0098] The wetting agent is selected from block polyethers, modified anions, EO / PO block copolymers, such as GY-W04, GY-W07, and Atlas G-500;

[0099] The defoaming agent is selected from silicone defoaming agents, such as GY-X60;

[0100] The thickener is selected from one or a combination of magnesium aluminum silicate and xanthan gum;

[0101] The antifreeze agent is selected from polyols such as ethylene glycol, propylene glycol, and glycerol;

[0102] The preservative is selected from isothiazolinones and sodium benzoate.

[0103] The above substances are sequentially placed in a reaction kettle according to the formula ratio, mixed evenly, 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.

[0104] Main technical indicators of suspension concentrate: suspension rate not less than 90%, pH 4-8, persistent foaming not more than 50 mL (after 1 minute), 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.

[0105] 2. Wettable powder

[0106] MDPQ5 technical 1%-90%, dispersant 3%-15%, wetting agent 2%-10%, filler to 100%;

[0107] Dispersants include carboxylates and alkylnaphthalene sulfonate polycondensates, such as GY-D800, Dispersol PSR 19, and Dispersol BB4.

[0108] The wetting agent is selected from anionic wetting agents, such as one or a combination of GY-WS01 and Multiwet 8269;

[0109] The filler is selected from kaolin and corn starch.

[0110] The above substances are mixed evenly according to the formula ratio, and then jet milled and mixed to obtain wettable powder. The main equipment includes mixer, jet mill, etc.

[0111] The main technical indicators of wettable powder are: 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 qualified thermal storage stability determined according to GB / T 19137 method.

[0112] 3. Water dispersible granules

[0113] MDPq5 technical material 1%-80%, dispersant 3%-12%, wetting agent 1%-10%, disintegrant 1%-10%, binder 0%-8%, filler to 100%;

[0114] The dispersant is selected from carboxylates, lignin sulfonates, alkylnaphthalene sulfonate polycondensates, such as GY-D800, Dispersol PSR 19, DM04;

[0115] The wetting agent is selected from polycarboxylates, anions, such as sodium lauryl sulfonate, alkylnaphthalene sulfonate formaldehyde condensate;

[0116] The disintegrant is selected from one or more combinations of urea, inorganic salts, sucrose, such as wgwin D909S, sucrose, ammonium sulfate, and urea;

[0117] The binder is selected from one or more combinations of polyethylene glycol 6000, modified polyvinyl alcohol, and carboxymethyl cellulose;

[0118] The filler is selected from corn starch and diatomaceous earth.

[0119] The above materials are mixed evenly according to the formula ratio, and then mixed to obtain coarse powder after air flow crushing. Then, appropriate amount of water is added to knead and granulate. The main equipment includes mixer, air flow crusher, granulator, dryer, etc.

[0120] The main technical indicators of water-dispersible granules are: 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 qualified thermal storage stability determined according to GB / T19137 method.

[0121] 4. EC

[0122] MDPq5 technical 5%-45%, pyraclostrobin technical 5%, emulsifier 1%-10%, solvent to 100%;

[0123] The emulsifier is selected from one or a combination of Nongru 500#, Nongru 400#, Nongru 600#, and Atlox 4838B;

[0124] The solvent is selected from solvent oil S150, mineral oil or dimethylformamide.

[0125] Dissolve the technical drug and emulsifier in a solvent, mix according to the formula, and allow to stand for filtration. The main equipment is a stirred tank. Key technical specifications for emulsifiable concentrates include: moisture content no greater than 2%, sustained foaming no greater than 60 mL (after 1 minute), pH 4-8, and compliance with 200-fold dilution emulsion stability, cold storage stability, and hot storage stability as determined by methods in accordance with GB / T 1603, GB / T 19136, and GB / T 19137.

[0126] 5. Microemulsion

[0127] MDPq5 technical 0.5%-60%, emulsifier 3%-20%, solvent 1%-30%, cosolvent 0%-5%, water to 100%;

[0128] The emulsifier is selected from anionic phosphates, such as Atplus 310;

[0129] The solvent is selected from one or more combinations of xylene, cyclohexanone, and dimethylformamide;

[0130] The cosolvent is selected from n-butanol or n-pentanol.

[0131] 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.

[0132] Main technical indicators of microemulsion: qualified transparent temperature range (0-50℃), persistent foaming of no more than 30 mL (after 1 minute), pH 4-8, and 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.

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 methyl 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 solution, 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, and then dichloromethane is added for extraction, the organic layer is washed with saturated NaHCO3 solution, and after removing the solvent from the organic layer, the organic layer is passed through a chromatography column, and the chromatography column uses methanol:dichloromethane in a volume ratio of 1:20 as the mobile phase.

4. A use of the quinoline compound as claimed in claim 1 as an agricultural fungicide, characterized in that: The control target of the agricultural fungicide is Rhizoctonia solani ( Rhizoctonia solani ), Alternaria alternata ( Alternaria alternate )、Pyricularia oryzae( Pyricularia oryzae ).

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

6. A bactericidal composition comprising the quinoline compound according to claim 1, characterized in that: The invention also contains other active ingredients; the active ingredient is pyraclostrobin; and the mass ratio of the quinoline compound to pyraclostrobin is 8:2-9:

1.

7. The bactericidal composition according to claim 6, characterized in that The quinoline compound is used as an effective ingredient in the sterilization composition, and its content is 0.1 wt%-90 wt%.

8. The bactericidal composition according to claim 6, characterized in that The content of the quinoline compound in the sterilization composition is 1 wt%-80 wt%.

9. The bactericidal composition according to claim 6, characterized in that The content of the quinoline compound in the sterilization composition is 5 wt%-50 wt%.

10. The bactericidal composition according to claim 6, characterized in that The control target of the fungicidal composition is Rhizoctonia solani ( Rhizoctonia solani ), Alternaria alternata ( Alternaria alternate )、Pyricularia oryzae( Pyricularia oryzae ); The crops controlled by the fungicidal composition are selected from tobacco or rice.

11. The bactericidal composition according to claim 6, characterized in that The bactericidal composition further comprises other inert ingredients; The dosage form of the bactericidal composition is selected from suspension, granules, wettable powder, water-dispersible granules, emulsifiable concentrate, aqueous emulsion or microemulsion.

12. The bactericidal composition according to claim 11, characterized in that The inert component is selected from one or more of fillers, wetting agents, dispersants, defoamers, antifreeze agents, solvents, emulsifiers, preservatives, disintegrants, and pigments.

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