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Synthetic method and application of quinazolinone compounds containing 1,2,4-triazolethione Schiff base

A technology of triazolethione Schiff base and quinazolinone is applied in the synthesis and application fields of quinazolinone compounds containing 1,2,4-triazolethione Schiff base, and can solve the problem of high toxicity , low efficacy, etc.

Inactive Publication Date: 2016-04-27
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the problems of high toxicity, low efficacy and drug resistance of traditional fungicides, it is particularly urgent to develop new agricultural fungicides that are green, efficient and highly selective

Method used

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  • Synthetic method and application of quinazolinone compounds containing 1,2,4-triazolethione Schiff base
  • Synthetic method and application of quinazolinone compounds containing 1,2,4-triazolethione Schiff base
  • Synthetic method and application of quinazolinone compounds containing 1,2,4-triazolethione Schiff base

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1: Compound 3-((4-(benzylamino)-5-thione-4,5-dihydro-1 H -1,2,4-triazol-3-yl)methyl)quinazoline-4(3 H )-ketone synthesis:

[0043] (1) Preparation of quinazoline-4-one

[0044] Add 9.0g (59.54mmol) methyl anthranilate and 3mL (79.52mmol) formic acid successively into a 100mL three-necked flask, stir well, add 13mL (327.3mmol) formamide, heat up to 130-140°C for reflux reaction, after 6h Stop the reaction, pour the reaction liquid into an appropriate amount of cold water after cooling, a large amount of white solids precipitate, continue to stir for 0.5h, filter with suction, wash with water, dry, and recrystallize with absolute ethanol to obtain 4.10 g of white flocs, with a yield of 47.1 %.

[0045] (2) 2-(4-oxoquinazoline-3-(4 H )-yl) preparation of ethyl acetate

[0046]Add 3.00g (20.53mmol) quinazolin-4-one, 60mL acetone and 3.00g potassium carbonate in sequence to a 100mL single-necked flask, and slowly add 3.85g (22.58mmol) ethyl bromoacetate in aceto...

Embodiment 2

[0056] Example 2: Compound 3-((4-((pyridine-2-methenyl)amino)-5-thione-4,5-dihydro-1 H -1,2,4-triazol-3-yl)methyl)quinazoline-4(3 H )-Synthesis of ketone (Compound No. F2 ):

[0057]

[0058] Steps (1)-(5) are the same as Steps (1)-(5) of Embodiment 1;

[0059] Step (6) was synthesized according to the method and conditions of step (6) in Example 1, except that pyridine-2-carboxaldehyde was used as the raw material and purified after reaction to obtain a dark green solid with a yield of 54.5% m.p.238-240°C. 1 HNMR (DMSO- d 6 ,500MHz) δ :5.47(s,2H),7.57-7.62(m,2H),7.71(d, J =8.00Hz,1H),7.87(t, J =8.00Hz,1H),8.02(t, J =7.60Hz,1H),8.16(t, J =7.60Hz,2H),8.50(s,1H),8.76(d, J =5.00Hz,1H),10.47(s,1H),14.12(s,1H); 13 CNMR (DMSO- d 6 ,125MHz) δ :41.03,121.91,122.12,126.66,127.06,127.86,127.94,135.30,137.90,147.88,148.34,148.52,150.73,151.77,160.51,160.71,162.60.IR(KBr,cm -1 ) v :3443,3031,1696,1617;Anal.CalcdforC 17 h 13 N 7 OS:C,56.19;H,3.61;N,26.98.Found:C,56.58...

Embodiment 3

[0060] Embodiment three: compound 3-((4-((((1 H -indole-3-methenyl)amino)-5-thione-4,5-dihydro-1 H -1,2,4-triazol-3-yl)methyl)quinazoline-4(3 H )-Synthesis of ketone (Compound No. F3 ):

[0061]

[0062] Steps (1)-(5) are the same as Steps (1)-(5) of Embodiment 1;

[0063] Step (6) was synthesized according to the method and conditions of step (6) in Example 1, except that indole-3-carboxaldehyde was used as a raw material, and a yellow solid was obtained after purification after reaction, with a yield of 56.4%. m.p.>250°C. 1 HNMR (DMSO- d 6 ,500MHz) δ :5.42(s,2H),7.17(t, J =7.45Hz,1H),7.28(t, J =7.45Hz,1H),7.53(d, J =8.00Hz,1H),7.58(t, J =8.00Hz,1H),7.70(d, J =8.00Hz,1H),7.87(t, J =7.50Hz,1H),8.11-8.17(m,3H),8.47(s,1H),9.79(s,1H),12.07(s,1H),13.82(s,1H); 13 CNMR (DMSO- d 6 ,125MHz) δ :41.30,110.30,112.90,121.92,122.14,122.64,123.86,124.65,126.65,127.86,127.89,135.25,136.37,137.93,147.25,148.40,1468.47,160.58 -1 ) v :3258,3064,2930,1695,1616;Anal.Calcdfor...

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Abstract

The invention discloses a preparation method and a bacteriostatic activity of plant pathogen prevention and treatment compounds quinazolinone compounds containing a 1,2,4-triazolethione Schiff base, and concretely relates to compounds represented by general formula (I), and a preparation method thereof. The quinazolinone target compounds containing the 1,2,4-triazolethione Schiff base are synthesized from methyl ortho-aminobenzoate, methanamide, ethyl bromoacetate, hydrazine hydrate, carbon disulfide, potassium hydroxide and aromatic aldehyde through the steps of ring closure, alkylation, hydrazinolysis, salt formation, ring closure and a Schiff base reaction. Compounds F11 and F19 have better Xanthomonas oryzae and Xanthomonas axonopodis pv. citri inhibition activity than a contrast medicate bismerthiazol under 200mg / mL or 100mg / mL; and the synthesized compounds have medium to excellent Sclerotinia scleotiorum inhibition activity, and compounds F4, F5, F6, F8, F9, F17 and F25 have broad-spectrum inhibition activity on six test fungi.

Description

technical field [0001] The invention relates to the field of chemical technology, in particular to a preparation method of a quinazolinone compound containing 1,2,4-triazolethione Schiff base and its effect on rice bacterial blight and citrus canker, etc. Bacteria, fungi such as wheat head blight, pepper fusarium wilt, apple rot, cucumber botrytis, rape sclerotinia, tomato botrytis and other fungi have inhibitory effect. Background technique [0002] Plant diseases are a major factor restricting the sustainable development of agriculture. Among them, plant bacterial diseases and plant fungal diseases are the most common and difficult to control, seriously threatening human food security. The rice flax spot disease that occurred in Bangladesh in 1942 caused 2 million people to starve to death; the epidemic of potato late blight in Ireland from 1844 to 1846 caused a nationwide famine; Wheat stripe rust causes huge economic losses. Due to the problems of high toxicity, low ef...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/06C07D401/14C07D403/14A01P1/00A01P3/00
CPCC07D403/06C07D401/14C07D403/14
Inventor 鲍小平闫柏任杨岚范治江
Owner GUIZHOU UNIV
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