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Pyridezinone-group-containing butenolide compounds and use thereof

A technology of pyridazinone butenyl lactone and compound, applied in the field of chemistry

Active Publication Date: 2019-11-01
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the pyridazinone butenyl lactone compound containing pyridazinone group shown in the general formula I of the present invention has no report

Method used

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  • Pyridezinone-group-containing butenolide compounds and use thereof
  • Pyridezinone-group-containing butenolide compounds and use thereof
  • Pyridezinone-group-containing butenolide compounds and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0180] Example 1: Preparation of intermediate 3-(1-hydroxyethyl)-4-phenyl-1-oxaspiro[4.5]dec-3-en-2-one

[0181] The intermediate 3-acetyl-4-phenyl-1-oxaspiro[4.5]dec-3-en-2-one (2.70 g, 0.01 mol) was dissolved in 30 mL of ethanol, and NaBH was added thereto 4 (0.57g, 0.015mol), stirred at room temperature for 1h, after the reaction was monitored by TLC, the solvent was evaporated under reduced pressure, then extracted with ethyl acetate and water, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and reduced Press precipitation to obtain 2.50 g of a white solid with a melting point of 114-115°C and a yield of 92%. 1 H NMR (600MHz, CDCl 3 )δ:0.95-1.95+1.64-1.79(m,10H,cyclohexyl-10H),1.40(d,J=6.6Hz,3H,CH 3 ), 3.07(d, J=9.6Hz, 1H, OH), 4.37(q, 1H, CH), 7.13-7.15(m, 2H, Ph-3, 5-2H), 7.44-7.45(m, 3H, Ph-2,4,6-3H); 13 C NMR (CDCl 3 ,150MHz)δ:21.91,23.12,24.23,33.21(J=68.7Hz),63.14,88.53,127.35,128.70,129.09,129.90,131.28,166.0...

Embodiment 2

[0182] Example 2: Preparation of intermediate 3-(1-chloroethyl)-4-phenyl-1-oxaspiro[4.5]dec-3-en-2-one

[0183] The intermediate 3-(1-hydroxyethyl)-4-phenyl-1-oxaspiro[4.5]dec-3-en-2-one (2.72 g, 0.01 mol) was dissolved in 20 mL of dichloromethane, Thionyl chloride (1 mL) was added dropwise under ice bath, then stirred at room temperature for 2 h, after the reaction was monitored by TLC, the solvent and excess thionyl chloride were evaporated under reduced pressure, water and ethyl acetate were added thereto for extraction, and the organic phase was Wash with saturated brine, dry over anhydrous magnesium sulfate, filter, and precipitate under reduced pressure to obtain 2.61 g, a white solid, melting point 126-127°C, yield 90% 250 . 1 HNMR (600MHz, CDCl 3 )δ: 1.05-1.11+1.55-1.82(m, 10H, cyclohexyl-10H), 1.71(d, J=7.2Hz, 3H, CH 3 ), 4.63(q,H,CH),7.19-7.21(m,2H,Ph-3,5-2H),7.47-7.48(m,3H,Ph-2,4,6-3H); 13 CNMR (CDCl 3 ,150MHz)δ:21.77,22.42,24.23,33.12(J=21.6Hz),48.42,87.48,127...

Embodiment 3

[0184] Example 3: Compound 2-tert-butyl-4-chloro-5-(1-(2-oxo-4-phenyl-1-oxaspiro[4.5]dec-3-en-3-yl)ethane Preparation of oxy)pyridazin-3(2H)-one (compound 8-9)

[0185] 3-(1-hydroxyethyl)-4-phenyl-1-oxaspiro[4.5]dec-3-en-2-one (2.72g, 0.01mol), potassium carbonate (1.66g, 0.01 2mol) , 2-tert-butyl-4,5-dichloropyridazin-3(2H)-one (commercially available, 2.42g, 0.011mol), dissolved in 20mLN,N-dimethylformamide, the reaction mixture was heated at 80 After reaction at ℃ for 1 h, TLC monitored the completion of the reaction, added ethyl acetate and water for extraction, washed the organic phase with saturated brine, dried over anhydrous magnesium sulfate, filtered, and precipitated under reduced pressure, and the residue was column chromatographed (eluent was ethyl acetate Ester and petroleum ether (boiling range 60-90°C, volume ratio 1:4) to obtain compound 8-9, 2.87g, colorless oil, yield 63% 254 . 1 H NMR (300MHz, CDCl 3 )δ:0.80-1.90(m,10H,cyclohexyl-10H),1.58(d,J=6.6Hz,3H,...

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Abstract

The invention belongs to the field of chemistry, and particularly relates to pyridezinone-group-containing butenolide compounds and use thereof. Structural formulae of the compounds are shown as a general formula I in which substitutes are defined in the description. The compounds of the general formula I show excellent activity against a variety of germs in agriculture or other fields, and can beadvantageously used to protect important plants in agriculture and horticulture, livestock and breeding stocks, as well as the environment where humans often go from harm caused by germs.

Description

technical field [0001] The invention belongs to the field of chemistry, and in particular relates to a pyridazinone-containing butenyl lactone compound and its application. Background technique [0002] Patent CN104370891 announced that 5-(butenolactone-3-ethylidene)-2-aminoimidazolinone compounds represented by the following general formula TB are effective against rice sheath blight, rape sclerotinia and capsicum phytophthora, etc. A variety of plant pathogenic bacteria have good bactericidal effect. [0003] [0004] Patent WO 9619469 discloses 4-substituted phenylbutenolactone compounds represented by the following general formula for the treatment of cyclooxygenase 2-mediated diseases. [0005] (Y can be selected from O; R 5 R 6 =O or S) [0006] However, there is no report on the pyridazinone-containing butenolactone compound with the structure shown in the general formula I of the present invention. Contents of the invention [0007] The purpose of the pre...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12C07D405/14C07D417/14A01N43/58A01N43/78A01P3/00
CPCC07D405/12C07D405/14C07D417/14A01N43/58A01N43/78
Inventor 关爱莹王明安孙芹杨金龙赵宇
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD