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1-substituted-5-trifluoromethyl-4-pyrazol-1,3,4-oxadiazole thioether or sulfone derivatives and application of derivatives

A technology of oxadiazole sulfide and trifluoromethyl, which is applied in the field of agricultural plant pathogen prevention and control, and can solve problems such as drug resistance, irrational use, and human health threats

Active Publication Date: 2015-08-12
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the shortcomings of synthetic chemical fungicides and long-term unreasonable use, some serious problems have gradually been exposed: such as the emergence of drug resistance, threats to human health, etc.

Method used

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  • 1-substituted-5-trifluoromethyl-4-pyrazol-1,3,4-oxadiazole thioether or sulfone derivatives and application of derivatives
  • 1-substituted-5-trifluoromethyl-4-pyrazol-1,3,4-oxadiazole thioether or sulfone derivatives and application of derivatives
  • 1-substituted-5-trifluoromethyl-4-pyrazol-1,3,4-oxadiazole thioether or sulfone derivatives and application of derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1: Preparation of 1-phenyl-4-((5-methylthio)-1,3,4-oxadiazolyl)-5-trifluoromethyl-1H-pyrazole (A1)

[0039] 1) 1-Phenyl-5-trifluoromethyl-1 H - Preparation of 4-pyrazole hydrazide

[0040]

[0041] In a 250 mL three-neck flask equipped with a condenser tube and a thermometer, add ethyl ethoxymethylene trifluoroacetoacetate (66.05 mmol), phenylhydrazine (69.35 mmol), and ethanol (50 mL) in sequence, and heat to 80 o C, reacted for 24 h, TLC detected the end of the reaction, lowered to room temperature, distilled off the solvent under reduced pressure, and directly dissolved the remaining oily liquid in 80% hydrazine hydrate solution (100 mmol) without purification, heated to reflux for 2 hours, TLC detected the end of the reaction , the system was lowered to normal temperature, suction filtered, the solid was washed with water and dried to obtain the product, a white solid with a yield of 81.8% and a melting point of 146–148 o C; 1 H-NMR (500 MHz, DMSO-D 6...

Embodiment 2

[0048] Example 2: Preparation of 1-methyl-4-((5-methylthio)-1,3,4-oxadiazolyl)-5-trifluoromethyl-1H-pyrazole (A14)

[0049] 1) Preparation of 1-methyl-5-trifluoromethyl-1H-4-pyrazole hydrazide

[0050]

[0051] In a 250 mL three-necked flask with a condenser tube and a thermometer, add ethyl ethoxymethylene trifluoroacetoacetate (66.05 mmol), methylhydrazine (40%) (69.35 mmol), ethanol (50 mL) in sequence, Heat to 80 o C, reacted for 24 h, TLC detected the end of the reaction, lowered to room temperature, distilled off the solvent under reduced pressure, and directly dissolved the remaining oily liquid in 80% hydrazine hydrate solution (100 mmol) without purification, heated to reflux for 2 hours, TLC detected the end of the reaction , the system was lowered to normal temperature, suction filtered, the solid was washed with water and dried to obtain the product, a white solid with a yield of 64.6% and a melting point of 115-116 o C; 1 H-NMR (500 MHz, DMSO-D 6 ): δ : 9...

Embodiment 3

[0058] Example 3: 1-phenyl-4-((5-ethanesulfonyl)-1,3,4-oxadiazolyl)-5-trifluoromethyl-1 H - Preparation of pyrazole (B1)

[0059]

[0060] In a 25 mL three-neck flask with a condenser tube and a thermometer, add 1-phenyl-4-((5-ethylthio)-1,3,4-oxadiazolyl)-5-trifluoromethyl -1 H -pyrazole (615.8 mu mol), acetic acid (3 mL), and KMnO 4 (615.8 mu mol), react at room temperature for 24 hours, TLC detects the end of the reaction, adjust the pH value to 7~8, filter with suction, and purify the crude product by column chromatography (dichloromethane: ethyl acetate = 10:1), the target compound B1. White solid, yield 64.6%, melting point 72~73 o C; 1 H NMR (500 MHz, DMSO- d6 ) δ : 8.58 (s, 1H, pyrazole H), 7.64-7.58 (m, 5H, benzene H), 3.78 (q, J = 7.3 Hz, 2H, S-CH 2 ), 1.31 (t, J = 7.4 Hz, 3H, CH 3 ); 13 C NMR (125 MHz, DMSO- d 6 ) δ : 161.83, 159.90, 141.92, 138.81, 131.12, 130.02, 126.75, 120.40, 118.24, 107.54, 50.07, 7.15; ν 3089, 2981, 2936, 1627, 1595...

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Abstract

The invention discloses a kind of 1-substituted-5-trifluoromethyl-4-pyrazol-1,3,4-oxadiazole thioether or sulfone derivatives and application of the derivatives. The derivatives have the structures represented by general formulae A and B shown in the specification. 1-substituted-5-trifluoromethyl-4-pyrazol-1,3,4-oxadiazole compounds are synthesized from ethyl trifluoroacetoacetate by the following five reactions: esterification, ring closure, hydrazinolysis, ring closure and substitution. The compounds have certain inhibition effects to plant bacterial diseases or plant fungous diseases and can be used as pesticides and pesticide additives for preventing and controlling the plant bacterial diseases or the plant fungous diseases.

Description

technical field [0001] The invention relates to the field of antibacterial agents, and discloses the application of 1,3,4-oxadiazole sulfide or sulfone derivatives containing 1-substituted-5-trifluoromethyl-4-pyrazole in the prevention and control of agricultural plant pathogens . Background technique [0002] In view of the major bacterial and fungal diseases in my country's agriculture at present, scientifically and efficiently discovering green candidate pesticides with potential market vitality is an important task in the basic research of new pesticide creation in my country. In the development of fungicides, synthetic chemical fungicides have played an important role in antibacterial, bactericidal and ensuring stable yields of agricultural and forestry crops. However, due to the shortcomings of synthetic chemical fungicides and long-term unreasonable use, some serious problems have gradually been exposed: such as the emergence of drug resistance and threats to human h...

Claims

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Application Information

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IPC IPC(8): C07D413/04C07D417/14A01N43/824A01P3/00
CPCA01N43/82C07D413/04C07D417/14
Inventor 杨松张滕滕叶意强周翔薛伟吴志兵陈玉婷
Owner GUIZHOU UNIV
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