Benzamide compound containing pyrimidine structure as well as preparation method and application of benzamide compound

Abstract

The invention also discloses a benzamide compound containing a pyrimidine structure, which is shown as a structural formula: # imgabs0 #, a preparation method of the benzamide compound and application of the benzamide compound to a plant fungicide. The synthesis steps are relatively simple, the disclosed compound can well inhibit the growth of some phytopathogens, and a new compound is provided for developing plant bactericides.

Description

Technical Field

[0001] The invention belongs to the technical field of pesticide synthesis, relates to plant fungicides, and in particular to a benzamide compound containing a pyrimidine structure, a preparation method and an application thereof. Background Art

[0002] According to the United Nations Food and Agriculture Organization (FAO), up to 40% of food crops are lost each year due to plant diseases and insect pests. The global economic losses caused by plant diseases exceed US$220 billion each year. In order to deal with various diseases in agricultural production, agricultural fungicides have emerged. However, with the widespread use of various fungicides, the problem of drug resistance of pathogens has become more serious year by year. In order to deal with this problem, it is urgent to develop plant fungicides with novel structures.

[0003] Pyrimidine compounds are a class of heterocyclic compounds closely related to life activities, and are widely found in nature, such as cytosine, uracil and thymine. Pyrimidine compounds have anti-tumor, antiviral, bactericidal, insecticidal, acaricidal and herbicidal activities, and are widely used in the fields of medicine and pesticides. In 1968, the British company Brunner Mond launched the first pyrimidine fungicide, ethidium bromide. Currently, more than 10 varieties of such fungicides have entered the pesticide market, such as azoxystrobin, cyprodinil, fluazifop and cyprodinil.

[0004] Amide structure is an important type of active group, which is widely present in various pesticide molecules, such as herbicides acetochlor and flupyralid, insecticides flonicamid and chlorfenapyr, fungicides oxadiazine and flupyralid, etc. Therefore, it is of great significance to design and develop new amide fungicides based on pyrimidine structure. Summary of the invention

[0005] In order to overcome the defects of the prior art, the present invention provides a benzamide compound containing a pyrimidine structure, a preparation method thereof, and an application thereof in inhibiting plant pathogens.

[0006] Technical Solution

[0007] A benzamide compound containing a pyrimidine structure, the chemical structure of which is shown in the following formula:

[0008]

[0009] Wherein: R is H, a halogen atom, an alkyl group, a halogenated alkyl group or a nitro group, etc.

[0010] The second object of the present invention is to disclose a method for preparing the above-mentioned benzamide compounds containing pyrimidine structure.

[0011] The preparation method of the benzamide compound containing a pyrimidine structure comprises: dissolving cyprodinil (A) and a benzoyl chloride compound (B) in a reaction solvent in proportion, stirring, and performing thin layer chromatography to detect the reaction until the reaction is complete, washing the reaction solution with a saturated sodium bicarbonate solution, drying with anhydrous sodium sulfate, and concentrating under reduced pressure to obtain a crude product, and then purifying the crude product with column chromatography to obtain the benzamide compound containing a pyrimidine structure. The reaction equation is:

[0012]

[0013] Wherein, R is H, a halogen atom, an alkyl group, a halogenated alkyl group or a nitro group.

[0014] In a preferred disclosed example of the present invention, the ratio of the amount of cyprodinil (A) to the amount of the benzoyl chloride compound (B) is 1:1-4.

[0015] In a preferred embodiment of the present invention, the reaction solvent is a polar aprotic solvent, preferably dichloromethane.

[0016] In a preferred embodiment of the present invention, the reaction temperature is from room temperature to the reflux temperature of the reaction solvent.

[0017] In a preferred embodiment of the present invention, the eluent for column chromatography is a volume ratio of V 石油醚 :V 乙酸乙酯 = a mixture of 10:1 to 1:10.

[0018] The benzamide compounds containing pyrimidine structure prepared by the present invention have good anti-plant pathogenic bacteria activity, and can well inhibit plant pathogens such as cucumber wilt, peanut brown spot, apple ring pattern, wheat stripe blight, corn spot, watermelon anthrax, rice seedling blight, tomato early blight, wheat fusarium, rice blast, pepper phytophthora, rape sclerotium, cucumber gray mold and rice stripe blight, and the inhibitory effect on peanut brown spot, wheat stripe blight and rape sclerotium is particularly prominent.

[0019] The third object of the present invention is to disclose a plant fungicide, which at least comprises the above-mentioned benzamide compound containing a pyrimidine structure and an auxiliary material, wherein the mass percentage of the benzamide compound containing a pyrimidine structure is 1 to 99.9999%.

[0020] Furthermore, the botanical fungicide is in the form of any one of emulsifiable concentrate, suspension, wettable powder, dust, granule, aqueous solution, poison bait, mother liquor or mother powder.

[0021] Beneficial Effects

[0022] Based on the "intermediate derivatization method", the present invention acylates the imino group (-NH-) in the fungicide cyprodinil developed by Ciba-Geigy AG (now Syngenta) to form a new benzamide compound containing a pyrimidine structure, which has good activity in inhibiting plant pathogens. The synthesis steps of the present invention are relatively simple, and the prepared benzamide compound containing a pyrimidine structure can well inhibit the growth of some plant pathogens, providing a reference for the development of new plant fungicides. DETAILED DESCRIPTION

[0023] The present invention is described in detail below in conjunction with the embodiments so that those skilled in the art can better understand the present invention, but the present invention is not limited to the following embodiments.

[0024] Example 1

[0025]

[0026] Synthesis of I-1: Add benzoyl chloride (8 mmol) and 5 mL of anhydrous dichloromethane to the reaction flask and dissolve. Dissolve cyprodinil (2 mmol, 0.45 g) and triethylamine (6 mmol, 0.83 mL) in 15 mL of anhydrous dichloromethane and place in a constant pressure dropping funnel, then add dropwise to the reaction flask, stir at room temperature, and detect the reaction to be complete by thin layer chromatography. After the reaction is completed, the reaction solution is washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which is then purified by column chromatography (V 石油醚 :V 乙酸乙酯 =8:1~2:1) to obtain 0.53 g of yellow solid, namely compound Ⅰ-1, with a yield of 80%. 1 H NMR (400MHz, CDCl3) δ7.64–7.46(m,2H),7.42–7.12(m,8H),6.74(s,1H),2.34(s,3H),1.69(s,1H),0.71(s,2H),0.52(s,2H).

[0027] Example 2

[0028]

[0029] Synthesis of I-2: Add 2-methylbenzoyl chloride (8 mmol) and 5 mL of anhydrous dichloromethane to the reaction flask and dissolve. Dissolve cyprodinil (2 mmol, 0.45 g) and triethylamine (6 mmol, 0.83 mL) in 15 mL of anhydrous dichloromethane and place in a constant pressure dropping funnel, then add dropwise to the reaction flask, stir at room temperature, and detect the reaction to be complete by thin layer chromatography. After the reaction is completed, the reaction solution is washed with a saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which is then purified by column chromatography (V 石油醚 :V乙酸乙酯 =10:1~1:1) to obtain 0.55 g of white solid, namely compound Ⅰ-2, with a yield of 80%. 1 H NMR (400MHz, CDCl3) δ7.46–7.26(m,5H),7.25–7.11(m,3H),7.07–6.92(m,1H),6.69 (s,1H),2.50(s,3H),2.27(s,3H),1.68(s,1H),0.79(d,J=6.0Hz,2H),0.61(s,2H).

[0030] Example 3

[0031]

[0032] Synthesis of I-3: 3-fluorobenzoyl chloride (8 mmol) and 5 mL of anhydrous dichloromethane were added to the reaction flask to dissolve. Cyprodinil (2 mmol, 0.45 g) and triethylamine (6 mmol, 0.83 mL) were dissolved in 15 mL of anhydrous dichloromethane and placed in a constant pressure dropping funnel, and then added dropwise to the reaction flask, stirred at room temperature, and the reaction was complete after thin layer chromatography. After the reaction was completed, the reaction solution was washed with a saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which was then purified by column chromatography (V 石油醚 :V 乙酸乙酯 =5:1~3:1) to obtain 0.52 g of white solid, namely compound Ⅰ-3, with a yield of 75%. 1 H NMR (400MHz, CDCl3) δ7.42–7.36(m,2H),7.34–7.20(m,6H),7.12–7.03(m,1H),6. 75(s,1H),2.33(s,3H),1.82–1.64(m,1H),0.85–0.75(m,2H),0.60–0.50(m,2H).

[0033] Example 4

[0034]

[0035] Synthesis of I-4: 3-chlorobenzoyl chloride (8 mmol) and 5 mL of anhydrous dichloromethane were added to the reaction flask to dissolve. Cyprodinil (2 mmol, 0.45 g) and triethylamine (6 mmol, 0.83 mL) were dissolved in 15 mL of anhydrous dichloromethane and placed in a constant pressure dropping funnel, and then added dropwise to the reaction flask, stirred at room temperature, and the reaction was complete after thin layer chromatography. After the reaction was completed, the reaction solution was washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which was then purified by column chromatography (V 石油醚 :V 乙酸乙酯=5:1~1:2) to obtain 0.52 g of gray solid, namely compound Ⅰ-4, with a yield of 72%. 1 H NMR (400MHz, CDCl3) δ7.56–7.51(m,1H),7.43–7.27(m,5H),7.25–7.14(m,1H),7.22 –7.20(m,3H),2.31(s,3H),1.75–1.65(m,1H),0.85–0.74(m,2H),0.60–0.49(m,2H).

[0036] Example 5

[0037]

[0038] Synthesis of I-5: 3-bromobenzoyl chloride (8 mmol) and 5 mL of anhydrous dichloromethane were added to the reaction flask to dissolve. Cyprodinil (2 mmol, 0.45 g) and triethylamine (6 mmol, 0.83 mL) were dissolved in 15 mL of anhydrous dichloromethane and placed in a constant pressure dropping funnel, and then added dropwise to the reaction flask, stirred at room temperature, and the reaction was complete after thin layer chromatography. After the reaction was completed, the reaction solution was washed with a saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which was then purified by column chromatography (V 石油醚 :V 乙酸乙酯 =8:1~1:1) to obtain 0.62 g of white solid, namely compound Ⅰ-5, with a yield of 76%. 1 H NMR (400MHz, CDCl3) δ7.72–7.66(m,1H),7.50–7.45(m,1H),7.43–7.36(m,3H),7.33–7.27(m,1H),7.25–7.19(m ,2H),7.12(t,J=7.8Hz,1H),6.75(s,1H),2.30(s,3H),1.75–1.67(m,1H),0.85–0.76(m,2H),0.59–0.51(m,2H).

[0039] Example 6

[0040]

[0041] Synthesis of I-6: 3-nitrobenzoyl chloride (8 mmol) and 5 mL of anhydrous dichloromethane were added to the reaction flask to dissolve. Cyprodinil (2 mmol, 0.45 g) and triethylamine (6 mmol, 0.83 mL) were dissolved in 15 mL of anhydrous dichloromethane and placed in a constant pressure dropping funnel, and then added dropwise to the reaction flask, stirred at room temperature, and the reaction was complete after thin layer chromatography. After the reaction was completed, the reaction solution was washed with a saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which was then purified by column chromatography (V 石油醚 :V 乙酸乙酯 =6:1~3:1) to obtain 0.56 g of white solid, namely compound Ⅰ-6, with a yield of 75%. 1 H NMR (400MHz, CDCl3) δ8.35-8.29(m,1H),8.24–8.19(m,1H),7.90–7.83(m,1H),7.49(t,J=8.0Hz,1H),7.45–7.35(m 2H),7.37–7.32(m,1H),7.29–7.26(m,1H),7.25–7.22(m,1H),6.77(s,1H ),2.32(s,3H),1.75–1.65(m,1H),0.85–0.76(m,2H),0.56–0.49(m,2H).

[0042] Example 7

[0043]

[0044] Synthesis of I-7: 3-trifluoromethylbenzoyl chloride (8 mmol) and 5 mL of anhydrous dichloromethane were added to the reaction flask to dissolve. Cyprodinil (2 mmol, 0.45 g) and triethylamine (6 mmol, 0.83 mL) were dissolved in 15 mL of anhydrous dichloromethane and placed in a constant pressure dropping funnel, and then added dropwise to the reaction flask, stirred at room temperature, and the reaction was complete after thin layer chromatography. After the reaction was completed, the reaction solution was washed with a saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which was then purified by column chromatography (V 石油醚 :V 乙酸乙酯 =5:1~2:1) to obtain 0.56 g of white solid, namely compound Ⅰ-7, with a yield of 71%. 1H NMR (400MHz, CDCl3) δ7.74(s,1H),7.69(d,J=8.2Hz,1H),7.60(d,J=7.8Hz,1H),7.44–7.37(m,3H),7.34–7.28 (m,1H),7.26–7.23(m,2H),6.74(s,1H),2.29(s,3H),1.73-1.63(m,1H),0.83–0.75(m,2H),0.52–0.45(m,2H).

[0045] Example 8

[0046]

[0047] Synthesis of I-8: 4-iodobenzoyl chloride (8 mmol) and 5 mL of anhydrous dichloromethane were added to the reaction flask to dissolve. Cyprodinil (2 mmol, 0.45 g) and triethylamine (6 mmol, 0.83 mL) were dissolved in 15 mL of anhydrous dichloromethane and placed in a constant pressure dropping funnel, and then added dropwise to the reaction flask, stirred at room temperature, and the reaction was complete after thin layer chromatography. After the reaction was completed, the reaction solution was washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which was then purified by column chromatography (V 石油醚 :V 乙酸乙酯 =8:1~1:1) to obtain 0.59 g of brown solid, namely compound Ⅰ-8, with a yield of 65%. 1 H NMR (400MHz, CDCl3) δ7.66–7.59(m,2H),7.42 -7.35(m,2H),7.31-7.27(m,1H),7.25 -7.17(m,4H),6.74(s,1H),2.30(s,3H),1.74–1.66(m,1H),0.85–0.76(m,2H),0.55–0.47(m,2H).

[0048] Example 9

[0049]

[0050] Synthesis of I-9: 4-iodobenzoyl chloride (8 mmol) and 5 mL of anhydrous dichloromethane were added to the reaction flask to dissolve. Cyprodinil (2 mmol, 0.45 g) and triethylamine (6 mmol, 0.83 mL) were dissolved in 15 mL of anhydrous dichloromethane and placed in a constant pressure dropping funnel, and then added dropwise to the reaction flask, stirred at room temperature, and the reaction was complete after thin layer chromatography. After the reaction was completed, the reaction solution was washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which was then purified by column chromatography (V 石油醚 :V 乙酸乙酯=10:1~1:1) to obtain 0.40 g of white solid, namely compound Ⅰ-9, with a yield of 58%. 1 H NMR (400MHz, CDCl3) δ7.43–7.33(m,4H),7.27–7.24(m,1H),7.23–7.18(m,2H),7.06(d,J=8.0Hz,2H ),6.72(s,1H),2.32(s,3H),2.31(s,3H),1.74–1.60(m,1H),0.80–0.72(m,2H),0.55–0.48(m,2H).

[0051] Example 10

[0052]

[0053] Synthesis of I-10: Add 2-fluorobenzoyl chloride (8 mmol) and 5 mL of anhydrous dichloromethane to the reaction flask and dissolve. Dissolve cyprodinil (2 mmol, 0.45 g) and triethylamine (6 mmol, 0.83 mL) in 15 mL of anhydrous dichloromethane and place in a constant pressure dropping funnel, then add dropwise to the reaction flask, stir at room temperature, and detect the reaction to be complete by thin layer chromatography. After the reaction is completed, the reaction solution is washed with a saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which is then purified by column chromatography (V 石油醚 :V 乙酸乙酯 =8:1~1:1) to obtain 0.45 g of gray solid, namely compound Ⅰ-10, with a yield of 65%. 1 H NMR(400MHz, CDCl3)δ7.65–7.56(m 1H),7.45-7.37(m,2H),7.36–7.27(m,4H),7.14(t,J=7.4Hz,1H),6.90(t,J=9.4Hz,1H),6.73(s,1H),2.25(s,3H),1.75 -1.60,(m,1H),0.81–0.68,(m,2H),0.55–0.45,(m,2H).

[0054] Embodiment 11

[0055]

[0056] Synthesis of I-11: Add 2-chlorobenzoyl chloride (8 mmol) and 5 mL of anhydrous dichloromethane to the reaction flask and dissolve. Dissolve cyprodinil (2 mmol, 0.45 g) and triethylamine (6 mmol, 0.83 mL) in 15 mL of anhydrous dichloromethane and place in a constant pressure dropping funnel, then add dropwise to the reaction flask, stir at room temperature, and detect the reaction to be complete by thin layer chromatography. After the reaction is completed, the reaction solution is washed with a saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which is then purified by column chromatography (V 石油醚 :V 乙酸乙酯 =5:1~1:1) to obtain 0.44 g of white solid, namely compound Ⅰ-11, with a yield of 60%. 1 H NMR (400MHz, CDCl3) δ7.66–7.55(m,1H),7.40(t,J=7.8Hz,2H),7.36–7.27(m,4H),7.14(t,J=7.5Hz,1H), 6.90(t,J=9.4Hz,1H),6.73(s,1H),2.27(s,3H),1.75–1.63(m,1H),0.82-0.68(m,2H),0.55–0.45(m,2H).

[0057] Example 12

[0058]

[0059] Synthesis of I-12: Add 2-bromobenzoyl chloride (8 mmol) and 5 mL of anhydrous dichloromethane to the reaction flask and dissolve. Dissolve cyprodinil (2 mmol, 0.45 g) and triethylamine (6 mmol, 0.83 mL) in 15 mL of anhydrous dichloromethane and place in a constant pressure dropping funnel, then add dropwise to the reaction flask, stir at room temperature, and detect the reaction to be complete by thin layer chromatography. After the reaction is completed, the reaction solution is washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which is then purified by column chromatography (V 石油醚 :V 乙酸乙酯 =5:1~1:2) to obtain 0.69 g of yellow solid, namely compound Ⅰ-12, with a yield of 85%. 1 H NMR (400MHz, CDCl3) δ7.48-7.28(m,7H),7.26-7.23(m,1H),7.15(td,J=8.0,1.8Hz,1H ),6.70(s,1H),2.23(s,3H),1.73–1.65(m,1H),0.84–0.76(m,2H),0.66–0.55(m,2H).

[0060] Example 13

[0061]

[0062] Synthesis of I-13: Add 2-iodobenzoyl chloride (8 mmol) and 5 mL of anhydrous dichloromethane to the reaction flask and dissolve. Dissolve cyprodinil (2 mmol, 0.45 g) and triethylamine (6 mmol, 0.83 mL) in 15 mL of anhydrous dichloromethane and place in a constant pressure dropping funnel, then add dropwise to the reaction flask, stir at room temperature, and detect the reaction to be complete by thin layer chromatography. After the reaction is completed, the reaction solution is washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which is then purified by column chromatography (V 石油醚 :V 乙酸乙酯 =6:1~3:1) to obtain 0.61 g of yellow solid, namely compound Ⅰ-13, with a yield of 74%. 1 H NMR (400MHz, CDCl3) δ7.78(d,J=7.7Hz,1H),7.45-7.27(m,6H),7.25–7.19(m,1H),6.97(td,J=7.8,2.0Hz,1H),6.69(s,1H),2.22(s,3H),1.75 -1.62(m,1H),0.78-0.90(m,2H),0.70–0.60(m,2H).

[0063] Embodiment 14

[0064]

[0065] Synthesis of I-14: 4-chlorobenzoyl chloride (8 mmol) and 5 mL of anhydrous dichloromethane were added to the reaction flask to dissolve. Cyprodinil (2 mmol, 0.45 g) and triethylamine (6 mmol, 0.83 mL) were dissolved in 15 mL of anhydrous dichloromethane and placed in a constant pressure dropping funnel, and then added dropwise to the reaction flask, stirred at room temperature, and the reaction was complete after thin layer chromatography. After the reaction was completed, the reaction solution was washed with a saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which was then purified by column chromatography (V 石油醚 :V 乙酸乙酯 =8:1~1:1) to obtain 0.56 g of white solid, namely compound Ⅰ-14, with a yield of 62%. 1 H NMR (400MHz, CDCl3) δ7.47–7.42(m,2H),7.41–7.35(m,2H),7.31–7.27(m,1H),7.25-7.17( m,4H),6.74(s,1H),2.31(s,3H),1.75–1.66(m,1H),0.88–0.75(m,2H),0.63–0.47(m,2H).

[0066] Embodiment 15

[0067]

[0068] Synthesis of I-15: 4-bromobenzoyl chloride (8 mmol) and 5 mL of anhydrous dichloromethane were added to the reaction flask to dissolve. Cyprodinil (2 mmol, 0.45 g) and triethylamine (6 mmol, 0.83 mL) were dissolved in 15 mL of anhydrous dichloromethane and placed in a constant pressure dropping funnel, and then added dropwise to the reaction flask, stirred at room temperature, and the reaction was complete after thin layer chromatography. After the reaction was completed, the reaction solution was washed with a saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which was then purified by column chromatography (V 石油醚 :V 乙酸乙酯 =8:1~2:1) to obtain 0.47 g of white solid, namely compound Ⅰ-15, with a yield of 65%. 1 H NMR (400MHz, CDCl3) δ7.43–7.35(m,6H),7.31–7.27(m,1H),7.23–7.17(m,2H),6. 75(s,1H),2.31(s,3H),1.76–1.65(m,1H),0.88–0.77(m,2H),0.66–0.45(m,2H).

[0069] Example 16

[0070]

[0071] Synthesis of I-16: 4-nitrobenzoyl chloride (8 mmol) and 5 mL of anhydrous dichloromethane were added to the reaction flask to dissolve. Cyprodinil (2 mmol, 0.45 g) and triethylamine (6 mmol, 0.83 mL) were dissolved in 15 mL of anhydrous dichloromethane and placed in a constant pressure dropping funnel, and then added dropwise to the reaction flask, stirred at room temperature, and the reaction was complete after thin layer chromatography. After the reaction was completed, the reaction solution was washed with a saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which was then purified by column chromatography (V 石油醚 :V 乙酸乙酯 =5:1~1:1) to obtain 0.53 g of white solid, namely compound Ⅰ-16, with a yield of 65%. 1 H NMR (400MHz, CDCl3) δ8.17–8.09(m,2H),7.70–7.60(m,2H),7.43–7.37(m, 2H),7.35–7.29(m,1H),7.26–7.21(m,2H),6.76(s,1H),2.28(s,3H),1.76 -1.65(m,1H),0.85–0.76(m,2H),0.54–0.45(m,2H).

[0072] Example 17 Antibacterial activity test, the determination steps are as follows:

[0073] In vitro bactericidal test, mycelial growth rate determination method (plate method)

[0074] Dissolve a certain amount of the drug in an appropriate amount of acetone, then dilute it to the required concentration with an aqueous solution containing 200μg / mL emulsifier, then draw 1mL of the drug solution and inject it into the culture dish, then add 9mL of culture medium respectively, shake well to make a 50μg / mL drug-containing plate, and use the plate with 1mL of sterilized water as a blank control. Use a 4mm diameter puncher to cut the bacterial disc along the outer edge of the hyphae and move it to the drug-containing plate. Repeat each treatment three times. Place the culture dish in a constant temperature incubator at 24±1℃ for culture. After 48 hours, investigate the expansion diameter of the bacterial disc of each treatment, calculate the average value, and calculate the relative inhibition rate compared with the blank control.

[0075] Calculation formula: inhibition rate (%) = (D1-D2) / D1×100, wherein D1 is the average diameter of the blank control plaque, and D2 is the average diameter of the test sample plaque.

[0076] Table 1. Inhibitory activity of compounds (I-1 to I-16) against plant pathogens (50 μg / mL, inhibition rate %)

[0077]

[0078] Using the amide fungicide boscalid as a control, the fungicidal activity of 14 plant pathogens was tested. The test results showed that at a test concentration of 50 μg / mL, some compounds showed broad-spectrum inhibitory activity against the 14 tested species. Among them, the inhibitory activity of compound I-1 against rapeseed sclerotia was 93.1%, which was equivalent to the positive control drug boscalid (98.6%). The inhibitory effects on 10 species of cucumber wilt, apple ring pattern, wheat leaf blight, corn leaf spot, watermelon anthracnose, tomato early blight, wheat fusarium, rice blast, pepper phytophthora and cucumber gray mold were higher than or equivalent to the control drug boscalid.

[0079] The above descriptions are merely embodiments of the present invention and are not intended to limit the patent scope of the present invention. Any equivalent structure or equivalent process transformation made using the specification of the present invention, or directly or indirectly applied in other related technical fields, are also included in the patent protection scope of the present invention.

Claims

1. A benzamide compound containing a pyrimidine structure, characterized in that: The chemical structure is shown below: Wherein: R is H, a halogen atom, an alkyl group, a haloalkyl group or a nitro group.

2. A method for preparing the benzamide compound containing a pyrimidine structure as claimed in claim 1, characterized in that: include: Dissolve cyprodinil (A) and benzoyl chloride compound (B) in a reaction solvent in proportion, stir, and detect by thin layer chromatography until the reaction is complete. Wash the reaction solution with saturated sodium bicarbonate solution, dry with anhydrous sodium sulfate, and concentrate under reduced pressure to obtain a crude product, which is then purified by column chromatography to obtain a benzamide compound containing a pyrimidine structure. The reaction equation is: Wherein, R is H, a halogen atom, an alkyl group, a halogenated alkyl group or a nitro group.

3. The method for preparing the benzamide compound containing pyrimidine structure according to claim 2, characterized in that: The ratio is 1:1 to 4 between the amount of cyprodinil (A) and the amount of benzoyl chloride compound (B).

4. The method for preparing the benzamide compound containing pyrimidine structure according to claim 2, characterized in that: The reaction solvent is a polar aprotic solvent.

5. The method for preparing the benzamide compound containing pyrimidine structure according to claim 4, characterized in that: The reaction solvent is dichloromethane.

6. The method for preparing the benzamide compound containing pyrimidine structure according to claim 2, characterized in that: The reaction temperature is from room temperature to the reflux temperature of the reaction solvent.

7. The method for preparing the benzamide compound containing pyrimidine structure according to claim 2, characterized in that: The column chromatography, the eluent volume ratio V 石油醚 :V 乙酸乙酯 = a mixture of 10:1 to 1:

10.

8. An application of the benzamide compound containing a pyrimidine structure as claimed in claim 1, characterized in that: It is used to inhibit plant pathogens such as cucumber wilt, peanut brown spot, apple ring pattern, wheat stripe blight, corn spot, watermelon anthrax, rice seedling blight, tomato early blight, wheat fusarium, rice blast, pepper phytophthora, rapeseed sclerotium, cucumber gray mold or rice stripe blight, especially peanut brown spot, wheat stripe blight and rapeseed sclerotium.

9. A plant fungicide comprising at least the benzamide compound containing a pyrimidine structure as claimed in claim 1 and an auxiliary material, characterized in that: The mass percentage of the benzamide compound containing pyrimidine structure is 1 to 99.9999%.

10. The botanical fungicide according to claim 9, wherein the dosage form of the botanical fungicide is any one of emulsifiable concentrate, suspension concentrate, wettable powder, dust, granule, aqueous solution, poison bait, mother liquor or mother powder.

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