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8-hydroxyquinoline compound as well as preparation method and application thereof in preventing and treating agricultural disease

A technology of hydroxyquinoline and compounds, applied in the field of 8-hydroxyquinoline compounds and their preparation and application in the prevention and control of agricultural diseases, which can solve the problems of poor control effect, difficulty in disease control, increased and limited control costs, etc.

Inactive Publication Date: 2019-03-15
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the use of chemical fungicides is still one of the main measures to prevent and control crop diseases in agricultural production. However, the extensive use of chemical fungicides has also caused the rapid development of drug resistance for a long time. The problem of resistance is becoming more and more serious, and the service life of pesticides is shortened. The control effect is getting worse and worse, which makes disease control more difficult and costs more, and the drugs that can effectively control diseases are very limited

Method used

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  • 8-hydroxyquinoline compound as well as preparation method and application thereof in preventing and treating agricultural disease
  • 8-hydroxyquinoline compound as well as preparation method and application thereof in preventing and treating agricultural disease
  • 8-hydroxyquinoline compound as well as preparation method and application thereof in preventing and treating agricultural disease

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] Synthesis of Quinoline Derivatives (X-2~X-35)

[0012]

[0013] Its concrete synthetic operation is as follows:

[0014] 5-nitro-8 hydroxyquinoline was prepared according to the method reported in the literature. And 0.5g (2.63mmol) 5-nitro-8 hydroxyquinoline and 0.32mL formaldehyde were dissolved in 20ml absolute ethanol. To this solution was added 2 equivalents of the corresponding amine. The mixture was refluxed at 80°C for 24h. The reaction solution was filtered to obtain a precipitate, which was then dissolved in EtOH:H 2 O=1:1 solution was recrystallized to obtain the corresponding product.

Embodiment 2

[0016] The synthesis of X-2: experimental procedure is with embodiment 1.

[0017]

[0018] X-2 yellow-green solid, yield 80%; 1 H NMR (400MHz, DMSO-d 6 )δ9.33(dd,J=8.7,1.6Hz,1H), 8.61(d,J=4.0Hz,1H),8.59(s,1H),7.56(dd,J=8.7,4.1Hz,1H), 4.17(s,2H),3.11(s,4H),1.73(t,J=5.9Hz,4H). 13 C NMR (101MHz, DMSO-d 6 )δ158.94,148.08,136.65,135.17,132.68, 132.43,126.47,124.07,113.65,53.73,53.73,51.59,22.95,22.95.ESI-MS m / z:274.29[M+1] + .

Embodiment 3

[0020] The synthesis of X-3: experimental procedure is with embodiment 1.

[0021]

[0022] X-3 yellow solid, yield 90%; 1 H NMR (400MHz, DMSO-d 6 )δ9.35(d, J=8.7Hz, 1H), 8.61(s, 1H), 8.55(s, 1H), 7.55(dd, J=8.7, 4.1Hz, 1H), 4.59(s, 1H), 4.08(s,2H),2.94(s,2H),1.64(t,J=8.1Hz,2H),1.34(q,J=7.6Hz,2H),0.89(t,J=7.4Hz,3H). 13 C NMR (101MHz, DMSO-d 6 )δ 158.78,148.47,136.65,134.77,132.74,131.96,126.34,123.69,115.71,47.05,44.79,27.91, 19.72,13.96.MS-ESI m / z:276.31[M+1] + .

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Abstract

The invention discloses a hydroxyquinoline compound as well as a preparation method and application thereof in preventing and treating agricultural diseases. Testing results show that the compound hasremarkable activity upon corn leaf fulvia fulvum, cotton oxysporum, potato rhizoctonia solani kuhn, didymella bryoniae, fusarium oxysporum, wheat gibberella, rice blast, botrytis cinerea, lycium barbarum anthracnose, cotton anthracnose, sclerotinia sclerotiorum, pepper phytophthora blight, potato late blight, rhizoctonia solani, melon bacterial fruit plaque bacteria, grape meloidogynosis bacteria, Chinese cabbage erwinia carotovora, kiwi fruit anabrosis bacteria, pseudomonas lachrymans, ralstorinia solanacearum, rice bacterial leaf blight and rice bacterial stripe bacteria. The hydroxyquinoline compound is simple in preparation process, cheap and easy in raw material obtaining, high in product purity, good in bioactivity and wide in sterilization spectrum and has the potential of being developed as new fungicides.

Description

technical field [0001] The invention belongs to the technical field of pesticides, and discloses a new application of 8-hydroxyquinoline derivatives, in particular to the use of quinoline derivatives in the prevention and treatment of gibberella wheat, point mold corn leaf, cotton fusarium wilt, rice blast, etc. A series of plant fungal diseases caused by it and the control effect of a series of plant bacterial diseases caused by rice bacterial blight, kiwifruit canker and rice bacterial streak. Background technique [0002] Plant diseases threaten crop growth and food security, resulting in reduced yield or poor quality. According to statistics, the direct economic losses caused by plant diseases are as high as hundreds of billions of dollars every year, of which 70% to 80% are caused by plant fungi and bacterial diseases, which have brought serious economic losses and social problems. At present, the use of chemical fungicides is still one of the main measures to prevent ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/28C07D401/12A01N43/42A01N43/60A01N43/84A01P1/00A01P3/00
CPCA01N43/42A01N43/60A01N43/84C07D215/28C07D401/12
Inventor 刘映前杨冠洲尹晓丹彭静文赵中敏刘华朱佳凯杨余东
Owner LANZHOU UNIVERSITY
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