Triazole Mannich base compounds containing trifluoromethyl and piperazine, as well as preparation methods and application of triazole Mannich base compounds

A technology of trifluoromethyl compound, applied in the field of triazole Mannich base compounds, can solve the problems of bactericidal, herbicidal, and KARI enzyme inhibitory activity that has not been disclosed, and achieves good in vitro inhibitory activity effect.

Active Publication Date: 2015-12-02
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the preparation of nitrogen azole Mannich base compound has been reported (CN103288816, CN102276555), in the prior art, the preparation of the triazole Mannich base ...

Method used

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  • Triazole Mannich base compounds containing trifluoromethyl and piperazine, as well as preparation methods and application of triazole Mannich base compounds
  • Triazole Mannich base compounds containing trifluoromethyl and piperazine, as well as preparation methods and application of triazole Mannich base compounds
  • Triazole Mannich base compounds containing trifluoromethyl and piperazine, as well as preparation methods and application of triazole Mannich base compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Preparation method of compound 03.

[0026] Step A: Preparation of N-(p-tolyl)thiosemicarbazide

[0027]

[0028] Add 4.80 g (0.12 mol) NaOH, 7.60 g (0.10 mol) CS to 10.73 g (0.10 mol) p-toluidine in DMF (100 mL) solution 2 , stirred at 20-25° C. for 1 h, raised the temperature to 60-70° C., slowly added 18.75 g (0.30 mol) of hydrazine hydrate (80%) and continued stirring for 1 h. After cooling, an appropriate amount of ice water was added, and a precipitate precipitated out. Suction filtration and ethanol recrystallization gave 9.70 g of brown crystals, with a yield of 54%.

[0029] Step B: Preparation of 4-(p-tolyl)-5-trifluoromethyl-4H-1,2,4-triazole-3-thiol

[0030]

[0031] 5.00g (27.58mmol) of N-(p-tolyl)thiosemicarbazide and 6.29g (55.17mmol) of trifluoroacetic acid were heated and stirred under reflux for 8 hours, and the reaction solution was poured into an appropriate amount of ice water, and a precipitate was precipitated, filtered by suction, and was...

Embodiment 2

[0036] Preparation method of compound 13.

[0037] Step A: Preparation of N-(p-fluorophenyl)thiosemicarbazide

[0038]

[0039]Add 4.80 g (0.12 mol) NaOH, 7.60 g (0.10 mol) CS to 11.11 g (0.10 mol) of p-fluoroaniline in DMF (100 mL) 2 , stirred at 20-25° C. for 1 h, raised the temperature to 60-70° C., slowly added 18.75 g (0.30 mol) of hydrazine hydrate (80%) and continued stirring for 1 h. After cooling, an appropriate amount of ice water was added, and a precipitate precipitated out. Suction filtration and ethanol recrystallization gave 10.50 g of brown crystals, with a yield of 57%.

[0040] Step B: Preparation of 4-(p-fluorophenyl)-5-trifluoromethyl-4H-1,2,4-triazole-3-thiol

[0041]

[0042] 5.00g (24.79mmol) N-(p-fluorophenyl) thiosemicarbazide and 6.16g (49.58mmol) trifluoroacetic acid were heated, stirred and refluxed for 8 hours. 6.12 g of colorless crystals were separated by petroleum ether-ethyl acetate (15:1) column chromatography, and the yield was 94%. ...

Embodiment 3

[0055] Determination of Bactericidal Activity by Isolated Plate Method

[0056] Put the test bacteria into flakes and insert them into a petri dish containing 50 μg / mL liquid medicine, put them in a biochemical incubator at 25°C for dark cultivation, and investigate the antibacterial effect after 3 days. Each treatment was repeated 3 times. Those who only added sterile water but no medicine were used as the control. The results are shown in Table 3. (%)

[0057] Inhibition rate (%) = [(blank colony diameter - treated colony diameter) ÷ (blank colony diameter - 4)] × 100%

[0058] Table 3. The in vitro bactericidal activity of the compound (50 μg / mL, inhibition rate %)

[0059] No.

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Abstract

The invention belongs to the field of agricultural bactericides and herbicides, and particularly discloses triazole Mannich base compounds containing trifluoromethyl and piperazine, as well as preparation methods and application of the triazole Mannich base compounds. The triazole Mannich base compounds have structural formulas shown in formula I and formula II; in the structural formulas, R1 and R2 are defined as claim 1. The triazole Mannich base compounds have certain in-vitro inhibitory activities on such plant pathogens as cucumber fusarium wilt pathogens, peanut cercospora brown spot pathogens, apple ring spot pathogens, tomato early blight pathogens, wheat sharp eyespot pathogens and wheat scab pathogens, and particularly has relatively high in-vitro inhibitory activities on the apple ring spot pathogens and the wheat sharp eyespot pathogens. The triazole Mannich base compounds with the structural formulas shown in formula I and formula II both have certain weeding activities on oilseed rapes, and have relatively high in-vitro inhibitory activities on ketol-acid reductoisome-rase (KARI) of rice. The triazole Mannich base compounds are applicable to comprehensive control of the damage caused by bacteria and weeds, and inhibition on the KARI activity.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides and herbicides, and relates to a triazole Mannich base compound containing trifluoromethyl and piperazine and its preparation and application. Background technique [0002] As people's awareness of the importance of environmental protection and food safety is deepening, the requirements for pesticides are becoming more stringent. Green pesticides with low toxicity, high efficiency and environmental friendliness meet the new requirements of future development. The development of compounds with dual or even multiple activities can better meet the needs of agriculture that serve multiple purposes. KARI enzyme is one of the key enzymes mainly present in plants and microorganisms (such as bacteria and fungi), which plays an essential catalytic role in the biosynthesis of branched-chain amino acids and can be used as a target for designing herbicides or fungicides. 1,2,4-Triazoles are a class of ...

Claims

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Application Information

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IPC IPC(8): C07D403/12C07D249/12A01P3/00A01P1/00A01P13/00
CPCC07D249/12C07D403/12
Inventor 王宝雷李正名张丽媛张燕张晓李永红
Owner NANKAI UNIV
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