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Compound for preparing crop pathogenic bacterium prevention and control medicament and preparation method thereof

A compound and synthesis method technology, applied in the field of chemistry, can solve the problems of reduced antibacterial efficacy, high toxicity of non-target organisms, and difficulty in degrading

Active Publication Date: 2018-08-03
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, many currently used fungicides are highly toxic to non-target organisms and difficult to degrade in the environment, and the resistance of fungicides to fungicides is becoming stronger and stronger, which leads to the continuous reduction of the control effect of existing fungicides

Method used

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  • Compound for preparing crop pathogenic bacterium prevention and control medicament and preparation method thereof
  • Compound for preparing crop pathogenic bacterium prevention and control medicament and preparation method thereof
  • Compound for preparing crop pathogenic bacterium prevention and control medicament and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1: Compound 3-(3-((4-((2-fluorobenzylidene)amino)-5-methyl-4H-1,2,4-triazol-3-yl)thio) -2-hydroxypropyl) quinazolin-4 (3H)-ketone synthesis:

[0046] (1) Preparation of quinazoline-4-one

[0047] Add 9.0g (59.5mmol) of methyl anthranilate, 13mL (327.3mmol) of formamide and 3mL (79.5mmol) of formic acid in sequence in a 100mL three-necked flask, heat up to 130-140°C for reflux for 6 hours, stop the reaction, and wait for the reaction After the liquid was cooled to room temperature, an appropriate amount of cold water was added. At this time, a large amount of white solids were precipitated, and the stirring was continued for 0.5 h. Suction filtration, washing with water, drying, and ethanol recrystallization gave 4.10 g of white flocs, with a yield of 47.2%.

[0048] (2) Preparation of 3-(2,3-epoxypropyl)quinazolin-4(3H)-one

[0049] Add 1.0g (6.84mmol) quinazolin-4-one, 50mL acetone and 1.2g (8.89mmol) potassium carbonate to a 100mL single-necked bottle, stir ...

Embodiment 2

[0059] Example 2: Compound 3-(3-((4-((3-fluorobenzylidene)amino)-5-methyl-4H-1,2,4-triazol-3-yl)thio) -2-hydroxypropyl) quinazolin-4 (3H)-ketone synthesis:

[0060] (1) Intermediates 4-((3-fluorobenzylidene)amino)-5-methyl-4H-1,2,4-triazole-3-thiol and 3-(2,3-epoxypropylene Base) the preparation of quinazoline-4 (3H)-ketone: synthesis steps and process conditions are the same as embodiment one (1~5);

[0061] (2) Target product 3-(3-((4-((3-fluorobenzylidene)amino)-5-methyl-4H-1,2,4-triazol-3-yl)thio) -2-hydroxypropyl) quinazolin-4 (3H)-one preparation (compound number A2):

[0062]

[0063] The synthesis steps and process conditions are the same as in Example 1 (6), except that m-fluorobenzaldehyde is used as a raw material to obtain a white solid with a yield of 88.6%. m.p.160~162℃, 1 H NMR (500MHz, DMSO-d 6 )δ:8.86(s,1H),8.19(s,1H),8.11(d,J=10.0Hz,1H),7.80-7.70(m,3H),7.63(d,J=5.0Hz,1H), 7.61-7.58(m,1H),7.52-7.45(m,2H),5.65(d,J=5.0Hz,1H),4.27-4.23(m,1H),4.07(s,1H),3...

Embodiment 3

[0064] Example 3: Compound 3-(3-((4-((4-fluorobenzylidene)amino)-5-methyl-4H-1,2,4-triazol-3-yl)thio) -2-hydroxypropyl) quinazolin-4 (3H)-ketone synthesis:

[0065] (1) Intermediates 4-((4-fluorobenzylidene)amino)-5-methyl-4H-1,2,4-triazole-3-thiol and 3-(2,3-epoxypropylene Base) the preparation of quinazoline-4 (3H)-ketone: synthesis steps and process conditions are the same as embodiment one (1~5);

[0066] (2) Target product 3-(3-((4-((4-fluorobenzylidene)amine)-5-methyl-4H-1,2,4-triazol-3-yl)thio) -2-hydroxypropyl) quinazolin-4 (3H)-one preparation (compound number A3):

[0067]

[0068] The synthesis steps and process conditions are the same as those in Example 1 (6), except that p-fluorobenzaldehyde is used as a raw material to obtain a white solid with a yield of 56.3%. m.p.209~210℃, 1 H NMR (500MHz, DMSO-d 6 )δ:8.85(s,1H),8.19(s,1H),8.11(d,J=10.0Hz,1H),8.00-7.97(m,2H),7.79(t,J=5.0Hz,1H), 7.63(d, J=5.0Hz, 1H), 7.51(d, J=5.0Hz, 1H), 7.40(d, J=5.0Hz, 2H), 5.65(d,...

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Abstract

The invention discloses a preparation method of a quinazoline-4-ketone compound containing 3-thioether group-4-substituted benzylidene amidogen-1,2,4-triazole unit for preventing and controlling plantpathogenic bacteria, antibacterial activity, a compound shown as a general formula (I) and a preparation method thereof. The invention discloses a target compound prepared by using methyl anthranilate, methanamide, epoxy chloropropane, hydrazine hydrate, carbon bisulfide and substituted benzaldehyde as raw materials through six-step reaction; compounds A12, A15, A19, A21 and A22 have excellent inhibition activity on citrus canker germs; compounds A4, A6, A9, A10 and A19 show prominent inhibition activity on tobacco bacterial wilt; compounds A5, A6, A12, A15 and A21 have good inhibition capability on bacteria of rice bacterial blight.

Description

technical field [0001] The present invention relates to the field of chemical technology, in particular to a quinazoline-4-one compound containing 3-thioether-4-substituted phenylmethyleneamino-1,2,4-triazole units The preparation method and the use thereof have inhibitory effect on plant pathogenic bacteria such as rice bacterial blight, citrus canker bacillus and tobacco Ralstonia solanacearum. Background technique [0002] The world needs food, and agriculture needs pesticides. Crop fungus damage is not as easy to detect as insect damage, weed damage and rodent damage, so it will cause neglect and difficulty in prevention and control. Currently, the use of chemical fungicides to control crop fungal damage is a cost-effective method. [0003] From the advent of the first fungicide "Bordeau mixture" in 1898 to the discovery of "Thiram" in 1934, it marked the transition of fungicides from inorganic compounds to the era of organic matter, which also greatly promoted the dev...

Claims

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Application Information

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IPC IPC(8): C07D403/12A01N43/653A01P1/00
CPCA01N43/653C07D403/12
Inventor 鲍小平杨岚石军罗娜
Owner GUIZHOU UNIV
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