CN108689950B - [ (6-substituted-pyrimidin-4-yloxy) phenyl ] -3-methoxyacrylate methyl ester - Google Patents
[ (6-substituted-pyrimidin-4-yloxy) phenyl ] -3-methoxyacrylate methyl ester Download PDFInfo
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Abstract
The invention discloses a method for inhibiting cropsPathogen-active [ (6-substituted-pyrimidin-4-yloxy) phenyl]-3-methoxy methyl acrylate, relating to the technical field of biochemistry. It has the following structural general formula:
Description
Technical Field
The invention relates to the technical field of biochemistry, and relates to [ (6-substituted-pyrimidine-4-yloxy) phenyl ] -3-methoxy methyl acrylate and a preparation method thereof.
Background
In the existing agricultural development, disease control is a big problem which puzzles farmers. If the disease cannot be prevented and controlled in time, the disease develops rapidly in a short time, and the affected area is gradually enlarged. Seriously affecting the harvest of crops. With the widespread use of agricultural chemicals, the resistance of crop germs is getting stronger, and the development of high-efficiency and low-toxicity agricultural chemicals is an urgent problem. Therefore, the development of the novel pesticide can effectively delay the generation of drug resistance of pathogenic groups and play a key role in preventing and controlling plant diseases. The methoxyl acrylic ester bactericides are novel high-efficiency, broad-spectrum and systemic bactericides, are derived from a natural product Strobilurin, and are mitochondrial respiration inhibitors. It usually shows very good activity to the fungus (ascomycetes, basidiomycetes, oomycetes and fungi imperfecti) disease, has protection, treatment, eradicate, layer transfer and systemic action to the crops, meanwhile, the methoxy acrylic ester fungicide has high selectivity, is safe to the crops, people, livestock and beneficial organisms, has no pollution to the environment basically, can be used in the modes of stem and leaf spraying, seed treatment and the like. However, the pesticide resistance of crops and plants also exists, so that the modification of the methoxy acrylate compounds is necessary for developing novel methoxy acrylate bactericides.
Disclosure of Invention
The invention aims to provide [ (6-substituted-pyrimidine-4-yloxy) phenyl ] -3-methoxy methyl acrylate with broad-spectrum activity, and also aims to provide application of the methyl acrylate in inhibiting the activity of pathogenic bacteria of crops.
In order to achieve the purpose of the invention, the invention carries out structural modification on methoxyacrylate to synthesize [ (6-substituted-pyrimidin-4-yloxy) phenyl ] -3-methoxyacrylate, which has the following structural general formula:
the synthetic route of [ (6-substituted-pyrimidine-4-yloxy) phenyl ] -3-methoxy methyl acrylate of the invention is as follows:
(a) adding the compound 1, toluene, glacial acetic acid and phosphorus pentoxide into a three-necked bottle, and heating and refluxing. After the reaction is finished, cooling, adding water for washing, extracting by ethyl acetate, separating out an organic phase, and evaporating the solvent under reduced pressure to obtain a yellow solid compound 2. The product was used directly in the next reaction without purification.
(b) Adding the compound 2 and trimethyl orthoformate into a three-neck flask, stirring at room temperature until the solid is completely dissolved, and adding a catalyst zinc chloride. Stirring and heating, controlling the temperature to be 80-130 ℃, and cooling after the reaction is finished. And adding ethyl acetate and water into the reaction system, washing, separating an organic phase, and concentrating under reduced pressure to obtain a compound 3. The product was used directly in the next reaction without purification.
(c) The compound 3, methanol and sodium methoxide are mixed and stirred at the temperature of 0-10 ℃ for reaction, and after the reaction is finished, the compound 4 is directly used for the next reaction without being separated from a system.
(d) Slowly adding the compound 4 into a 1, 4-dioxane solution of 4, 6-dichloropyrimidine at a certain temperature, heating to 50-80 ℃, filtering off salt under reduced pressure when the solution is hot, and evaporating the solvent from the filtrate under reduced pressure to obtain a compound 5.
(e) Heating, refluxing and stirring the compound 5, methanol and sodium methoxide for reaction, cooling to room temperature after the reaction is completed, adding water and ethyl acetate, separating an organic phase, and distilling the organic phase under reduced pressure to obtain a compound 6.
(f) The mixture of the compound 5, toluene, phenol with different substituents, potassium carbonate, Dimethylformamide (DMF) and triethylene Diamine (DABCO) is stirred at 90-120 ℃. After the reaction is completed, water and ethyl acetate are added, an organic phase is separated, and the organic phase is evaporated under reduced pressure to obtain a compound 7, a compound 8, a compound 9, a compound 10, a compound 14, a compound 16 and a compound 18.
(g) And stirring a mixture consisting of the compound 5, toluene, the compound 8 or the compound 9 or the compound 10, potassium carbonate, DMF and DABCO, and reacting for 5 to 9 hours at the temperature of between 80 and 130 ℃. Cooling to room temperature, adding water and ethyl acetate, separating organic phase, drying with anhydrous sodium sulfate, evaporating under reduced pressure, and performing column chromatography to obtain compound 11, compound 12, and compound 13.
(j) Adding iron powder, concentrated hydrochloric acid, ethanol and water into the compound 14 or the compound 16 or the compound 18 respectively, stirring and reacting for 1h-4h at 50-80 ℃, supplementing concentrated hydrochloric acid, continuing to react for 3h-7h, cooling to room temperature, adding water and ethyl acetate, separating out a water phase, neutralizing with a saturated solution of sodium carbonate until the water phase is alkaline, extracting with ethyl acetate, concentrating under reduced pressure until the water phase is dry, and performing column chromatography to obtain a yellow compound 15, a compound 17 and a compound 19.
(k) The mixture of the compound 5, toluene, naphthol with different substituents, potassium carbonate, DMF and DABCO is stirred at 100-140 deg.C. After the reaction was completed, water and ethyl acetate were added, the organic phase was separated, and evaporated to dryness under reduced pressure to obtain compound 20, compound 21, compound 22, compound 23, and compound 24.
The invention has the beneficial effects that a series of azoxystrobin analogues are successfully synthesized, and experiments prove that: they have good inhibitory effect on cucumber wilt, peanut brown spot, apple ring streak, wheat grain withered, corn spot, watermelon anthracnose and rice bakanae. Especially, the inhibition rates of the compound 6 and the compound 19 on the cucumber fusarium wilt are respectively 71.4 percent and 72.0 percent; the compounds 11, 12, 21 and 23 have higher inhibition rates on peanut brown spot germs, and the inhibition rates are respectively 88.0%, 87.1% and 86.2%; the compounds 7, 9, 21, 10 and 22 have higher inhibition rates on the ring rot of apple, and the inhibition rates are respectively 94.1%, 93.1%, 93.0%, 92.3% and 92.2%; the compounds 7, 9, 10, 21, 20, 6, 16, 8, 19, 11, 24 and 18 have high inhibition rates on Rhizoctonia cerealis, and the inhibition rates are respectively 97.2%, 96.4%, 95.5%, 94.1%, 93.3%, 93.1%, 92.4%, 92.2%, 92.0%, 91.7%, 91.1% and 90.1%; the compounds 10, 9, 7 and 19 have higher inhibition rates on the corn leaf spot pathogen, and the inhibition rates are 79.3%, 78.2%, 73.7% and 73.0% respectively; the compounds 24, 19, 18 and 17 have higher inhibition rates on the watermelon colletotrichum gloeosporioides, and the inhibition rates are respectively 79.1%, 73.4%, 72.1% and 71.5%; the higher inhibition rates for bakanae disease of rice were 82.8%, 81.3%, 80.9%, 77.8%, 76.9%, 72.3%, 71.2% and 70.1% for compound 10, compound 9, compound 8, compound 7, compound 6, compound 19, compound 20 and compound 18, respectively. Therefore, the compound can effectively inhibit pathogenic bacteria on crops, has potential application value for the current situation that the drug resistance of crops is more serious, and has good development prospect.
Detailed Description
The invention will be further illustrated with reference to the following specific examples. These examples are intended to be illustrative of the invention only and are not intended to limit the scope of the invention as claimed.
Example 1: synthesis of Compound 2
Adding a compound 1(304g, 2mmol), toluene (2L), glacial acetic acid (0.5L) and phosphorus pentoxide (500g) into a reactor, heating and refluxing for 6h, cooling to room temperature after complete reaction, slowly adding ice water, extracting for 3 times with ethyl acetate, combining organic phases, extracting with saturated saline water, drying the organic phases with anhydrous sodium sulfate, concentrating under reduced pressure to dryness, and directly using the organic phases in the next reaction without purification. Taking out a small part of the product and carrying out column chromatography to obtain white needle crystals of the compound 2. Melting point of 48-50 ℃:1H-NMR (400Hz, CDCl 3): 3.72(s, 2H, CH2), 7.08-7.32 (m, 4H, Ph-H).
Example 2: synthesis of Compound 3
Taking the raw material in the previous step, adding trimethyl orthoformate (265g,2.5mmol) and zinc chloride (13.6g,0.1mol), heating to 110 ℃, continuing to react for 4h, and cooling after the reaction is finished. And adding ethyl acetate and water into the reaction system, washing, separating an organic phase, and concentrating under reduced pressure to obtain a compound 3. The product was used directly in the next reaction without purification. Taking out a small part of the obtained product, performing column chromatography to obtain a compound 3 which is a yellow-green solid and has a melting point of 27-29 ℃:1H-NMR (400Hz, CDCl3), 4.13(S, 3H, CH3), 7.06-7.13 (m, 2H, Ph-H), 7.18-7.21 (m, 1H, CH), 7.53-7.56 (m, 2H, Ph-H).
Example 3: synthesis of compound 4-phenol sodium salt
Adding methanol (2L) into the raw materials in the previous step, adding sodium methoxide (130g, 2.4mmol) into the raw materials in a salt bath, continuously stirring the mixture to react for 2 hours, and concentrating the reaction solution under reduced pressure to be directly used for the next reaction. And (2) adding a small amount of concentrate into dilute hydrochloric acid to neutralize until the pH value is 6, then extracting with ethyl acetate and water, concentrating the organic phase under reduced pressure until the organic phase is dry, and purifying by column chromatography to obtain a colorless transparent oily compound 4: 1H-NMR (400Hz, CDCl 3): 3.38(s, 3H, OCH3), 3.68(s, 3H, OCH3), 4.95(s, 1H, CH), 6.76-6.85 (m, 2H, Ph-H), 7.15-7.18 (m, 2H, Ph-H).
Example 4 Synthesis of Compound 5
Under the condition of room temperature, sodium carbonate (106g, 1mol),4, 6-dichloropyrimidine (300g, 2mol) and 1, 4-dioxane (2L) are stirred, then the sodium phenolate of the compound 4 is slowly added into the reaction liquid, the reaction is heated to 60 ℃, the reaction is continued for 6 hours, the salt is filtered off under reduced pressure while the reaction is hot, water and ethyl acetate are added after the reaction is cooled to room temperature, an organic phase is separated out, anhydrous sodium sulfate is dried, and the reaction is concentrated under reduced pressure to obtain a compound 5 which is a light yellow solid after purification. Melting point: 104 to 106 ℃. 1H-NMR (400Hz, CDCl 3): 3.60(s, 3H, CH3), 3.75(s, 3H, CH3), 6.79(s, 1H, CH), 7.17-7.45 (m, 4H, Ph-H), 7.46(s, 1H, Pyr-H), 8.58(s, 1H, Pyr-H).
EXAMPLE 5 Synthesis of Compound 6
Compound 5(1.03g, 3.4mmol), methanol (10ml), and sodium methoxide (0.18g, 3.4mmol) were heated under reflux and stirred for reaction, after completion of the reaction, cooled to room temperature, water and ethyl acetate were added, the organic phase was separated, evaporated under reduced pressure and subjected to column chromatography to give Compound 6(0.84g, 83%) as a white crystalline powder. 1H-NMR (400Hz, CDCl 3): 3.59(s, 3H, OCH3), 3.73(s, 3H, OCH3), 3.95(s, 3H, OCH3), 6.06(s, 1H, CH), 7.15-7.44 (m, 4H, Ph-H), 7.44(s, 1H, Pyr-H), 8.44(s, 1H, Pyr-H).
Example 6 Synthesis of Compound 7
A mixture of Compound 5(3.1g, 10mmol), toluene (25mL), phenol (1.1g,12.0mol), potassium carbonate (1.38g, 10mmol), DMF (2mL), DABCO (0.2g) was stirred and reacted at 100 ℃ for 6 h. After cooling to room temperature, water and ethyl acetate were added, the organic phase was separated, dried over anhydrous sodium sulfate, evaporated to dryness under reduced pressure, and column chromatography gave 7(3.51g, 96%) as a pale yellow solid. 1H-NMR (400Hz, CDCl 3): 3.60(s, 6H, OCH3), 3.75(s, 6H, OCH3), 6.14(s, 2H, CH), 6.95-7.48 (m, 12H, Ph-H), 7.45(s, 1H, Pyr-H), 8.42(s, 1H, Pyr-H).
The same procedure is followed as in example 6 for the preparation of compound 8, with o-hydroxyphenol instead of phenol. This gave 8 (2.87g, 75%) as a pale yellow solid, 1H-NMR (400Hz, CDCl 3): 3.60(s, 3H, OCH3), 3.78(s, 3H, OCH3), 5.80(s, 1H, OH), 6.20(s, 1H, CH), 6.59-7.46 (m, 8H, Ph-H), 7.56(s, 1H, Pyr-H), 8.44(s, 1H, Pyr-H).
The same preparation as in example 6 of compound 9, substituting phenol with m-hydroxyphenol, gave 9 (2.75g, 72%) as a pale yellow solid, 1H-NMR (400Hz, CDCl 3): 3.61(s, 3H, OCH3), 3.77(s, 3H, OCH3), 5.80(s, 1H, OH), 6.23(s, 1H, CH), 6.58-7.45 (m, 8H, Ph-H), 7.58(s, 1H, Pyr-H), 8.45(s, 1H, Pyr-H).
Preparation of Compound 10 of example 6, p-hydroxyphenol instead of phenol, gave 10 (2.60g, 68%) as a pale yellow solid, 1H-NMR (400Hz, CDCl 3): 3.61(s, 3H, OCH3), 3.77(s, 3H, OCH3), 5.80(s, 1H, OH), 6.21(s, 1H, CH), 6.58-7.45 (m, 8H, Ph-H), 7.57(s, 1H, Pyr-H), 8.46(s, 1H, Pyr-H).
Example 7 Synthesis of Compound 11
A mixture of compound 5(1.5g, 5mmol), toluene (20mL), compound 8(1.90g,5mol), potassium carbonate (0.69g, 5mmol), DMF (1mL), DABCO (0.1g) was stirred and reacted at 110 ℃ for 6 h. After cooling to room temperature, water and ethyl acetate were added, the organic phase was separated, dried over anhydrous sodium sulfate, evaporated to dryness under reduced pressure, and column chromatography gave 11(2.55g, 78%) as a yellowish solid, 1H-NMR (400Hz, CDCl 3): 3.60(s, 6H, OCH3), 3.75(s, 6H, OCH3), 6.24(s, 2H, CH), 7.06-7.48 (m, 12H, Ph-H), 7.46(s, 2H, Pyr-H), 8.42(s, 1H, Pyr-H).
Preparation of compound 12 as in example 7: change compound 8 for compound 9 gave 12(2.68g, 82%) as a yellowish solid, 1H-NMR (400Hz, CDCl 3): 3.60(s, 6H, OCH3), 3.75(s, 6H, OCH3), 6.23(s, 2H, CH), 7.08-7.49 (m, 12H, Ph-H), 7.47(s, 2H, Pyr-H), 8.41(s, 1H, Pyr-H).
Preparation of compound 13 as in example 7: change compound 8 for compound 10 gave 13(2.81g, 86%) as a yellow solid, 1H-NMR (400Hz, CDCl 3): 3.60(s, 6H, OCH3), 3.75(s, 6H, OCH3), 6.22(s, 2H, CH), 7.05-7.46 (m, 12H, Ph-H), 7.45(s, 2H, Pyr-H), 8.40(s, 1H, Pyr-H).
Example 8 Synthesis of Compound 14
The same preparation as in example 6, Compound 7, phenol o-nitrophenol, gave 14 (3.78g, 92%) as a yellow solid, 1H-NMR (400Hz, CDCl 3): 3.61(s, 3H, OCH3), 3.77(s, 3H, OCH3), 6.17(s, 1H, CH), 7.20-7.44 (m, 6H, Ph-H), 7.48(s, 1H, Pyr-H), 8.28-8.31 (m, 2H, Ph-H), 8.41(s, 1H, Pyr-H).
Example 9 Synthesis of Compound 15
Adding iron powder (0.56g, 10mmol), concentrated hydrochloric acid (2ml), ethanol (10ml) and water (2ml) into compound 14(2.0g, 5mmol), stirring at 60 ℃ for 2H, adding concentrated hydrochloric acid (2ml), continuing to react for 5H, cooling to room temperature, adding water and ethyl acetate, separating out the water phase, neutralizing with saturated solution of sodium carbonate to be alkaline, extracting with ethyl acetate, concentrating under reduced pressure to dryness, and performing column chromatography to obtain yellow compound 15(1.74g, 94%) 1H-NMR (400Hz, CDCl 3): 3.62(s, 3H, OCH3), 3.78(s, 3H, OCH3), 6.16(s, 1H, CH), 7.22-7.46 (m, 6H, Ph-H), 7.47(s, 1H, Pyr-H), 8.26-8.29 (m, 2H, Ph-H), 8.40(s, 1H, Pyr-H).
The same preparation as in example 6 for compound 7, phenol was m-nitrophenol, giving 16 (3.70g, 90%) as a yellow solid, 1H-NMR (400Hz, CDCl 3): 3.60(s, 3H, OCH3), 3.76(s, 3H, OCH3), 6.17(s, 1H, CH), 7.18-7.42 (m, 6H, Ph-H), 7.48(s, 1H, Pyr-H), 8.30-8.33 (m, 2H, Ph-H), 8.43(s, 1H, Pyr-H).
The same preparation as in example 9, compound 15, compound 14 was replaced with compound 16 to give 17 (1.78g, 96%) as a yellow solid 1H-NMR (400Hz, CDCl 3): 3.60(s, 3H, OCH3), 3.76(s, 3H, OCH3), 6.15(s, 1H, CH), 7.23-7.47 (m, 6H, Ph-H), 7.46(s, 1H, Pyr-H), 8.25-8.28 (m, 2H, Ph-H), 8.41(s, 1H, Pyr-H)
The same procedure as in example 6 for the preparation of Compound 7, phenol p-nitrophenol, gave 18 (3.82g, 93%) as a yellow solid, 1H-NMR (400Hz, CDCl 3): 3.62(s, 3H, OCH3), 3.78(s, 3H, OCH3), 6.18(s, 1H, CH), 7.19-7.43 (m, 6H, Ph-H), 7.48(s, 1H, Pyr-H), 8.29-8.32 (m, 2H, Ph-H), 8.42(s, 1H, Pyr-H).
The same preparation as that of compound 15 of example 9, substituting compound 14 for compound 18, gave yellow compound 19(1.81g, 98%) 1H-NMR (400Hz, CDCl 3): 3.61(s, 3H, OCH3), 3.77(s, 3H, OCH3), 6.15(s, 1H, CH), 7.21-7.45 (m, 6H, Ph-H), 7.48(s, 1H, Pyr-H), 8.25-8.28 (m, 2H, Ph-H), 8.43(s, 1H, Pyr-H).
EXAMPLE 10 Synthesis of Compound 20
A mixture of compound 5(3.1g 10mmol), toluene (25mL), methyl naphthol (1.73g,12.0mol), potassium carbonate (1.38g, 10mmol), DMF (2mL), DABCO (0.2g) was stirred and reacted at 120 ℃ for 6 h. After cooling to room temperature, water and ethyl acetate were added, the organic phase was separated, dried over anhydrous sodium sulfate, evaporated to dryness under reduced pressure, and column chromatography gave 20(2.7g, 65%) as a pale yellow solid. 1H-NMR (400Hz, CDCl 3): 3.59(s, 3H, OCH3), 3.74(s, 3H, OCH3), 6.17(s, 1H, CH), 6.70-7.40 (m, 11H, Ph-H), 7.45(s, 1H, Pyr-H), 8.41(s, 1H, Pyr-H).
The same preparation of compound 21 of example 10, using 2-methyl-1-naphthol as the naphthol, gave 21 as a pale yellow solid (2.7g, 65%). 1H-NMR (400Hz, CDCl 3): 1.41(s, 3H, CH3), 3.61(s, 3H, OCH3), 3.76(s, 3H, OCH3), 6.15(s, 1H, CH), 6.72-7.42 (m, 11H, Ph-H), 7.46(s, 1H, Pyr-H), 8.42(s, 1H, Pyr-H).
The same preparation of compound 22 as in example 10, using 6-methoxy-1-naphthol as the naphthol, gave 22(2.77g, 62%) as a pale yellow solid, 1H-NMR (400Hz, CDCl 3): 3.65(s, 3H, OCH3), 3.80(s, 3H, OCH3), 3.96(s, 3H, OCH3), 6.14(s, 1H, CH), 6.76-7.46 (m, 11H, Ph-H), 7.48(s, 1H, Pyr-H), 8.46(s, 1H, Pyr-H).
The same preparation of compound 23 of example 10, using 3-methoxy-2-naphthol as the naphthol, gave 23(2.9g, 65%) as a pale yellow solid, 1H-NMR (400Hz, CDCl 3): 3.61(s, 3H, OCH3), 3.78(s, 3H, OCH3), 4.01(s, 3H, OCH3), 6.15(s, 1H, CH), 6.79-7.50 (m, 11H, Ph-H), 7.51(s, 1H, Pyr-H), 8.52(s, 1H, Pyr-H).
The same preparation of compound 24 as in example 10, using 6-methoxy-2-naphthol as the naphthol, gave 24(2.68g, 60%) as a pale yellow solid, 1H-NMR (400Hz, CDCl 3): 3.66(s, 3H, OCH3), 3.81(s, 3H, OCH3), 3.99(s, 3H, OCH3), 6.15(s, 1H, CH), 6.77-7.47 (m, 11H, Ph-H), 7.49(s, 1H, Pyr-H), 8.48(s, 1H, Pyr-H).
Application example 1 test of in vitro antibacterial Activity of the Compound of the present invention
The experimental method comprises the following steps: the in vitro bacteriostatic activity test method comprises the following steps: dissolving a certain amount of test compound in dimethyl sulfoxide to prepare a solution with a certain concentration, and diluting the solution into a test solution with the concentration of 500mg/L by using Tween. Sucking 1mL of the solution, adding the solution into 9mL of Potato Dextrose Agar (PDA) culture medium, inoculating a test strain after the culture medium is completely solidified, culturing for 72 hours in a dark environment at 25 +/-1 ℃, measuring the diameter of a bacterial colony, and comparing with a blank control group to obtain the in vitro inhibition rate. See table 1.
As can be seen from Table 1, compounds 6 to 24 have certain inhibitory activity against cucumber fusarium oxysporum, peanut brown spot pathogen, ring rot of apple, wheat sharp eyespot pathogen, corn small spot pathogen, watermelon anthracnose pathogen and bakanae disease of rice, especially have good inhibitory effect against peanut brown spot pathogen, ring rot of apple and wheat sharp eyespot pathogen, and are worthy of further study.
TABLE 1 Experimental results of in vitro bacteriostatic activity test of the compounds 6-24 of the present invention
Claims (1)
- [ (6-substituted-pyrimidin-4-yloxy) phenyl ] -3-methoxyacrylate, having the formula:
(I)wherein R is。
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