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1-substituted-5-amino-4-pyrazol di-1,3,4-diazole sulfur ether or 1,3,4-diazole sulfone derivatives and application thereof

A technology of oxadiazole sulfide and oxadiazole sulfone, which is applied in the field of prevention and control of agricultural plant virus diseases, can solve economic losses, threaten the continuous, stable, and healthy development of the tobacco industry, and reduce local fiscal revenue, tobacco output and quality, etc. question

Active Publication Date: 2014-06-25
GUIZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the diseases that affect the normal growth of tobacco are mainly tobacco mosaic virus disease and cucumber mosaic virus disease. These diseases directly lead to a sharp decline in tobacco yield and quality, causing serious economic losses, and threatening the sustainable, stable, healthy development and prosperity of the tobacco industry in Guizhou Province. Local fiscal revenue

Method used

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  • 1-substituted-5-amino-4-pyrazol di-1,3,4-diazole sulfur ether or 1,3,4-diazole sulfone derivatives and application thereof
  • 1-substituted-5-amino-4-pyrazol di-1,3,4-diazole sulfur ether or 1,3,4-diazole sulfone derivatives and application thereof
  • 1-substituted-5-amino-4-pyrazol di-1,3,4-diazole sulfur ether or 1,3,4-diazole sulfone derivatives and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1: Preparation of 1-(3-chloropyridin-2-yl)-4-((5-methylthio)-1,3,4-thiadiazolyl)-5-amino-1H-pyrazole (A1)

[0039] 1) Preparation of 1-(3-chloropyridin-2-yl)-5-amino-1H-4-pyrazole hydrazide

[0040]

[0041]In a 250 mL three-neck flask equipped with a condenser tube and a thermometer, add ethyl ethoxymethylene acetate (62.1 mmol), 3-chloro-2-pyridinehydrazine (59.1 mmol), and ethanol (50 mL) in sequence, and heat to 80°C, reacted for 24 h, TLC detected the end of the reaction, lowered to room temperature, distilled off the solvent under reduced pressure, the remaining solid was directly dissolved in absolute ethanol (200 mL) without purification, and 80% hydrazine hydrate solution (100 mmol) was slowly added to the reaction solution, heated to reflux for 2 hours, TLC detected that the reaction was complete, the system was lowered to room temperature, filtered with suction, the solid was washed with ethanol, and dried to obtain the product, a white solid, wi...

Embodiment 2

[0048] Example 2: 1-(3-chloropyridin-2-yl)-4-((5-ethylthio)-1,3,4-oxadiazolyl)-5-amino-1H-pyrazole ( A22 ) preparation

[0049] 1) Preparation of 1-(3-chloropyridin-2-yl)-5-amino-1H-4-pyrazole hydrazide

[0050] Wherein the preparation and embodiment of 1-(3-chloropyridin-2-yl)-5-amino-1H-4-pyrazole hydrazide 1 exactly the same in .

[0051] 2) Preparation of 5-(5-amino-1-(3-chloropyridyl-2-yl)-1H-pyrazol-4-yl)-1,3,4-oxadiazole-2-thiol

[0052]

[0053] In a 250 mL three-neck flask with a condenser tube and a thermometer, add 1-(3-chloropyridin-2-yl)-5-amino-1H-4-pyrazole hydrazide (13.1 mmol), potassium hydroxide ( 13.1mol), carbon disulfide (26.1mmol) and ethanol (100 mL), stirred at room temperature for 24 hours, TCL detected the end of the reaction, removed the solvent, without further purification, directly added to 50% potassium hydroxide aqueous solution (100 mL), 50 o After stirring at C for 24 hours, the reaction was detected by TLC, suction filtered, the fil...

Embodiment 3

[0057] Example 3: 1-(3-chloropyridin-2-yl)-4-((5-ethanesulfonyl)-1,3,4-thiadiazolyl)-5-amino-1H-pyrazole ( B2 ) preparation

[0058]

[0059] In a 25 mL three-necked flask with a condenser tube and a thermometer, add 1-(3-chloropyridin-2-yl)-4-((5-ethylthio)-1,3,4-thiadiazolyl )-5-amino-1H-pyrazole (615.8 μmol), sodium tungstate (307.9 μmol), acetic acid (3 mL) and 30% H 2 O 2 (3.7 mmol), 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 B2. White solid, yield 76.3%. 1 H NMR (DMSO-d 6 ) δ: 8.60 (d, 1H, J = 3.5 Hz, pyridine H) 8.27(d, 1H, J = 8.1 Hz, pyridine H), 8.12 (s, 1H, pyrazole H), 7.66 (q, 1H, J = 8.1 Hz, pyridine H), 7.00 (s, 2H, NH 2 ), 3.71 (q, 2H, J = 7.5 Hz, CH 2 ), 1.30 (t, 3H, J = 6.9 Hz, CH 3 ) ; IR (KBr): ν 3404, 3288, 3074, 2974, 2935, 1602, 1550, 14...

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Abstract

The invention discloses 1-substituted-5-amino-4-pyrazol di-1,3,4-diazole sulfur ether or 1,3,4-diazole sulfone derivatives and an application thereof. Structures of the derivatives are as shown in formulas I and II, wherein R1 is alkyl, alkenyl, phenyl, substituted phenyl, benzyl, substituted benzyl, heterocyclic radical and substituted heterocyclic radical; and X is O and S. The compounds can be applied as pesticides and pesticide additives for preventing and treating plant virus diseases.

Description

technical field [0001] The invention relates to the field of antiviral agents, and discloses the use of 1-substituted-5-amino-4-pyrazole 1,3,4-oxadiazole sulfide or 1,3,4-oxadiazole sulfone derivatives in agriculture Applications in the control of plant virus diseases. Background technique [0002] At present, in my country's agricultural production, due to abnormal climate conditions, changes in the structure of the agricultural industry and its planting patterns, the hazards of agricultural and forestry diseases and insect pests have become increasingly serious, food safety and ecological security issues have become increasingly prominent, it is difficult to guarantee the development of the agricultural industry, and the agricultural ecological situation is severe. In particular, the increased resistance to traditional pesticides has led to unsatisfactory control effects of conventional pesticides; the excessive residues of agricultural products have seriously damaged the ...

Claims

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Application Information

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IPC IPC(8): C07D417/14C07D413/14A01N43/824A01P1/00
CPCA01N43/82C07D413/14C07D417/14
Inventor 吴志兵邝继清杨松张滕滕吴世喜张东阳胡德禹叶意强
Owner GUIZHOU UNIV
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