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Synthesis of azacytanthrin derivative and application of azacytanthrin derivative in bactericide for preventing and treating phytopathogen bacteria and fungi and plant virus-resistant preparation

A technology of plant pathogenic bacteria and heterotryptanthin, which is applied in the field of medicinal chemistry and pesticide application, and can solve the problems of high toxicity and reduced effect

Active Publication Date: 2022-07-29
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Long-term use of traditional pesticides, the generation of resistance will lead to a significant decline in effect, under the pressure of environmental impact, highly toxic and low-efficiency pesticides will also be gradually banned and eliminated

Method used

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  • Synthesis of azacytanthrin derivative and application of azacytanthrin derivative in bactericide for preventing and treating phytopathogen bacteria and fungi and plant virus-resistant preparation
  • Synthesis of azacytanthrin derivative and application of azacytanthrin derivative in bactericide for preventing and treating phytopathogen bacteria and fungi and plant virus-resistant preparation
  • Synthesis of azacytanthrin derivative and application of azacytanthrin derivative in bactericide for preventing and treating phytopathogen bacteria and fungi and plant virus-resistant preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0091] Example 1 Compound 4A-1 (pyrido[2',3':4,5]pyrimido[1,2-a]indol-5(11H)-one)

[0092] 2-Aminonicotinic acid (0.01 mol) was added to 25 mL of dry dichloromethane, thionyl chloride (0.05 mL) was added to reflux for 3 h, the solvent was spin-dried, chloroform was added quickly, and isatin (0.01 mol) was added In the reaction system, a catalytic equivalent of triethylamine (0.001 mol) was added dropwise, refluxed for 2 hours, monitored by TLC, and when the reaction was complete, the solvent was spin-dried and separated by column chromatography (dichloromethane / methanol was 40:1 elution) , the target compound 4A-1 was obtained.

[0093]

[0094] Orange-yellow solid, yield 65%. M.P.>300°C, 1H NMR (500MHz, DMSO-d6) δ 9.04 (dd, J=4.6, 2.2Hz, 1H), 8.67 (dd, J=7.8, 2.0Hz, 1H), 8.41(d, J=8.0Hz, 1H), 7.88(d, J=7.4Hz, 2H), 7.71(dd, J=7.8, 4.6Hz, 1H), 7.47(t, J=7.4Hz, 1H).

[0095] 13C NMR (101MHz, DMSO) δ182.76, 158.58, 157.70, 156.58, 148.08, 146.21, 138.42, 136.79, 127.75, 125...

Embodiment 2

[0097] Example 2 Compound 4A-2 (9-fluoropyrido[2',3':4,5]pyrimido[1,2-a]indol-5(11H)-one)

[0098] 2-Aminonicotinic acid (0.01 mol) was added to 25 mL of dry dichloromethane, thionyl chloride (0.05 mL) was added to reflux for 3 h, the solvent was spin-dried, chloroform was quickly added, and 5-fluoroisatin (0.01 mL) was added. mol) was added to the reaction system, and the triethylamine (0.001mol) of catalytic equivalent was added dropwise, refluxed for 2 hours, and TLC monitoring was completed. elution) to obtain the target compound 4A-2.

[0099]

[0100] Yellow solid, 62% yield. M.P.>300°C, 1H NMR (400MHz, DMSO) δ 9.09 (dd, J=4.6, 2.0Hz, 1H), 8.72 (dd, J=7.9, 2.0Hz, 1H), 8.47(dd,J=8.8,4.2Hz,1H),7.86(dd,J=7.1,2.7Hz,1H),7.76(ddd,J=11.8,6.6,2.9Hz,2H).

[0101] 13C NMR (101MHz, DMSO) δ181.95, 159.70, 158.42, 157.59, 156.75, 148.38, 142.51, 136.85, 125.34, 124.68, 124.44, 119.60, 119.23, 112.51.C14HFN3O2 [M+H6FN3O2] + , 268.0517; found, 268.0514.

Embodiment 3

[0102] Example 3 Compound 4A-3 (10-bromopyrido[2',3':4,5]pyrimido[1,2-a]indol-5(11H)-one)

[0103] 2-Aminonicotinic acid (0.01 mol) was added to 25 mL of dry dichloromethane, thionyl chloride (0.05 mL) was added to reflux for 3 h, the solvent was spin-dried, chloroform was rapidly added, and 4-bromoisatin (0.01 mL) was added. mol) was added to the reaction system, and the triethylamine (0.001mol) of catalytic equivalent was added dropwise, refluxed for 2 hours, and TLC monitoring was completed. elution) to obtain the target compound 4A-3.

[0104]

[0105] Yellow solid, 55% yield. M.P.>300°C, 1H NMR (400MHz, DMSO) δ 9.10 (dd, J=4.6, 2.0Hz, 1H), 8.73 (dd, J=7.9, 2.0Hz, 1H), 8.50(dd,J=7.8,0.9Hz,1H),7.78(ddd,6.3,4.7,3.2,2H),7.72(dd,J=8.1,0.9Hz,1H).

[0106] 13C NMR (101MHz, DMSO) δ180.39, 158.48, 157.61, 156.84, 147.79, 147.67, 138.99, 136.96, 132.01, 125.29, 121.12, 120.31, 119.48, 116.48.

[0107] C14H6BrN3O2[M+H] + ,327.9716;found,327.9715

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Abstract

The invention discloses a series of substituted azacytanthrin derivatives and application of the compounds as fungicides for preventing and controlling phytopathogen bacteria and fungi and plant virus resisting preparations, the general formula of the derivatives is shown in (I), and the definition of each substituent is detailed in the specification. The compound shown in the general formula has high bactericidal activity and plant virus resistance activity on phytopathogen bacteria such as rice bacterial blight and fungi such as rice blast, and can be used for preparing agricultural special-effect bactericides and tobacco mosaic virus resistance preparations.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry and pesticide application, and more particularly to the use of azatrypamine as a plant pathogenic bacteria, a fungicide and an anti-plant virus. Background technique [0002] The main diseases affecting the growth of crops are bacterial diseases, fungal diseases and plant virus diseases, which seriously affect the quality and safety of agricultural products and constitute a global food security problem. Poor control will lead to global social problems. For example, Xanthomonas oryzae pv.oryzae is an important bacterial disease worldwide. The pathogen is Xanthomonas oryzae. %-60%, even the particles are not harvested. Magnaporthe oryzae, a fungal disease, is one of the most destructive rice diseases in the world, and is known as "rice cancer". Tobacco mosaic virus (TMV), an RNA virus that spreads widely in commercial crops such as tobacco and vegetables, has strong infectivity and gre...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/14A01N43/90A01P1/00A01P3/00
CPCC07D471/14A01N43/90
Inventor 欧阳贵平张广龙王贞超龙雪莎汪从雨谭画元
Owner GUIZHOU UNIV
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