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Quinazolinone compound containing 1, 2, 4-triazole thioether and synthesizing method and application of quinazolinone compound

A technology of triazole sulfide and quinazolinone, which is applied in the field of chemistry, can solve the problems of high toxicity of organic fungicides, does not conform to the development of the times, environmental pollution, etc., and achieves good effect of inhibiting activity

Active Publication Date: 2015-08-12
北京传奇优声文化传媒有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented new type of chemicals called Quizolones has been developed by researchers working at Cornell University (Corn). These molecules contain specific nitrogen atoms within them which make it possible for this unique structure to fight against harmful microorganisms such as yeast or mold spores. They were found to exhibit strong anti-bactility even without being absorbed into their body through metabolism.

Problems solved by technology

This patented technical problem addressed in this patents relates to finding novel chemical substances called quaternary azolines or related structures that can be effective against various types of microbes like yeast cells without causing harmful effects when applied over large areas.

Method used

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  • Quinazolinone compound containing 1, 2, 4-triazole thioether and synthesizing method and application of quinazolinone compound
  • Quinazolinone compound containing 1, 2, 4-triazole thioether and synthesizing method and application of quinazolinone compound
  • Quinazolinone compound containing 1, 2, 4-triazole thioether and synthesizing method and application of quinazolinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1: Compound 3-((5-(benzylthio)-4-phenyl-4H-1,2,4-triazol-3-yl)methyl)quinazolin-4(3H)-one Synthesis:

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

[0047] Add 9.0 g (59.54 mmol) methyl anthranilate, 13 mL (327.3 mmol) formamide, and 3 mL (79.52 mmol) formic acid to a 100 mL three-necked flask in sequence, and heat up to 130-140 °C for reflux reaction; stop after 6 h After the reaction, the reaction liquid was cooled and poured into an appropriate amount of cold water, a large amount of white solids precipitated, stirred for 0.5 h, filtered with water, washed with water, dried, and recrystallized with absolute ethanol to obtain 4.10 g of white flocs, with a yield of 47.1% .

[0048] (2) Preparation of 2-(4-oxoquinazolin-3-(4H)-yl) ethyl acetate

[0049] Add 0.20 g (1.37 mmol) quinazolin-4-one, 5 mL acetone, 0.28 g (2.04 mmol) potassium carbonate to a 25 mL single-necked bottle, slowly drop 0.34 g (2.05 mmol) ethyl bromoacetate at room temperature, and heat up ...

Embodiment 2

[0060] Example 2: Compound 3-((5-((4-(tert-butyl)benzyl)thio)-4-phenyl-4H-1,2,4-triazol-3-yl)methyl) Synthesis of quinazolin-4-(3H)-one:

[0061] (1) Preparation of intermediate 3-((4-phenyl-5-mercapto-4H-1,2,4-triazol-3-yl)methyl)quinazolin-4-(3H)-one: Synthetic steps and processing conditions are with embodiment one (1~5);

[0062] (2) Target product 3-((5-((4-(tert-butyl)benzyl)thio)-4-phenyl-4H-1,2,4-triazol-3-yl)methyl) The preparation of quinazolin-4-(3H)-one (compound number A2):

[0063]

[0064] The synthesis steps and process conditions are the same as in Example 1 (6), the difference being that p-tert-butylbenzyl bromide is used as a raw material, and white flocs are obtained after recrystallization from ethanol-dichloromethane (10:1, v / v), and the yield is : 58.0%; m.p. 175~178 ℃.

[0065] IR (KBr, cm -1 ) v : 2962, 1685, 1610, 1172; 1 H NMR (CDCl 3 , 500 MHz) δ : 1.27 (s, 9H), 4.38 (s, 2H), 5.18 (s, 2H), 7.04 (d, J = 8.05 Hz, 2H), 7.19 (d, J = 8.00...

Embodiment 3

[0066] Example 3: Compound 3-((5-((4-nitrobenzyl)thio)-4-phenyl-4H-1,2,4-triazol-3-yl)methyl)quinazoline Synthesis of -4(3H)-one:

[0067] (1) Preparation of intermediate 3-((4-phenyl-5-mercapto-4H-1,2,4-triazol-3-yl)methyl)quinazolin-4-(3H)-one: Synthetic steps and processing conditions are with embodiment one (1~5);

[0068] (2) Target product 3-((5-((4-nitrobenzyl)thio)-4-phenyl-4H-1,2,4-triazol-3-yl)methyl)quinazoline - Preparation of 4(3H)-one (compound number A3):

[0069]

[0070] The synthesis steps and process conditions are the same as in Example 1 (6), except that p-nitrobenzyl chloride is used as a raw material, and red granular crystals are obtained after recrystallization from ethanol-dichloromethane (10:1, v / v). The yield is: 50.0%; m.p. 188~190℃.

[0071] IR (KBr, cm -1 ) v : 3076, 1672, 1610, 1165; 1 H NMR (CDCl 3 , 500 MHz) δ : 4.46 (s, 2H), 5.14 (s, 2H), 7.18 (d, J = 7.45 Hz, 2H), 7.50~7.45 (m, 4H), 7.53 (d, J = 8.60 Hz, 2H), 7.70 (d, J = 8...

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Abstract

The invention discloses a quinazolinone compound containing 1, 2, 4-triazole thioether and synthesizing method and application of quinazolinone compound. The quinazolinone compound for preventing and curing plant pathogens is indicated by the general formula (I). Methyl anthranilate, formamide, ethyl bromoacetate, hydrazine hydrate, phenyl isothiocyanate, substitution benzyl halide or 2-chlorine-5 chloromethyl pyridine is used as raw material and subjected to six-step reaction to synthesize the target compound. The quinazolinone compounds A7, A8 and A19 are good in inhibitory activity on rice bacterial leaf blight germs. The quinazolinone compound A19 is good in inhibitory activity on citrus canker germs. The inhibitory activity on wheat scab germs of the quinazolinone compounds A14 and A18 and the inhibitory activity on apple rotting germs of the quinazolinone compound A8 are equal to that of control chemical hymexazol.

Description

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Claims

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Application Information

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Owner 北京传奇优声文化传媒有限公司
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