Pyrazolo pyrimidine compound and application thereof

A technology of compounds and compositions, applied in the field of agricultural science, which can solve problems such as difficulty in producing groundbreaking research results

Inactive Publication Date: 2014-09-03
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, so far, most of the research and development of plant disease resistance activators is based on 1,2,3-thiadiazole, which makes it difficult to produce groundbreaking research results

Method used

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  • Pyrazolo pyrimidine compound and application thereof
  • Pyrazolo pyrimidine compound and application thereof
  • Pyrazolo pyrimidine compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0089] Synthesis of Example 1.4-benzylidenehydrazino-1-methyl-pyrazol[3,4-d]pyrimidine (P-1)

[0090] (1) Synthesis of 1-methyl-pyrazol[3,4-d]pyrimidin-4-one

[0091]

[0092] Weigh 5-amino-1-methylpyrazole-4-carboxylic acid ethyl ester (2g, 11.8mmol) in a 25mL single-necked flask, add 15mL formamide, heat to 180°C and stir for 5h, then cool to Room temperature, filtered, washed with ethanol (2 x 8 mL) without purification.

[0093] (2) Synthesis of 4-chloro-1-methyl-1-hydro-pyrazol[3,4-d]pyrimidine

[0094]

[0095] Weigh 1-methyl-1-hydrogen-pyrazol[3,4-d]pyrimidin-4-one (500mg, 3.3mmol) in a 25mL three-neck flask, measure 5mL redistilled phosphorus oxychloride and add , heated to reflux for 5 h, cooled to room temperature, evaporated the solvent under reduced pressure, added the remaining solid to ice water, neutralized with saturated sodium bicarbonate, extracted with ethyl acetate (25 mL), washed the organic phase with saturated sodium bicarbonate solution and wate...

Embodiment 2

[0102] Synthesis of Example 2.4-(3-nitrobenzylidene)-hydrazine-1-methyl-pyrazol[3,4-d]pyrimidine (P-2)

[0103]

[0104] Weigh 4-hydrazino-1-methyl-1-hydro-pyrazolo[3,4-d]pyrimidine (100mg, 609μmol) in a 25mL single-necked flask, measure 10mL of absolute ethanol, add 50mg of acetic acid dropwise , heated and stirred until the raw materials were completely dissolved, weighed 3-nitrobenzaldehyde (184mg, 1.2mmol) and added to the above reaction system, continued to heat and reflux for 2.5h, then cooled to room temperature, filtered, and the filter cake was washed with absolute ethanol, free Recrystallization from water and ethanol gave 153 mg of a white solid with a yield of 84% and a melting point of 306.3-308.7°C. 1 H NMR (400MHz, DMSO-d 6 )δ12.32(s,1H),8.51(s,1H),8.40-8.36(m,3H),8.26(dd,J 1 =8.0Hz,J 2 =8.4Hz,2H),7.77(dd,J 1 =8.0Hz,J 2 =7.6Hz,1H),3.97(s,3H). HRMS(EI / [M + ]): C 13 h 11 N 7 o 2 Calculated: 297.0974; Experimented: 297.0978.

Embodiment 3

[0105] Synthesis of Example 3.4-(2-fluoro-4-trifluoromethylbenzylidene)-hydrazine-1-methyl-pyrazol[3,4-d]pyrimidine (P-3)

[0106]

[0107] Weigh 4-hydrazino-1-methyl-1-hydro-pyrazolo[3,4-d]pyrimidine (100mg, 609μmol) in a 25mL single-necked flask, measure 10mL of absolute ethanol, add 50mg of acetic acid dropwise , heated and stirred until the raw materials were completely dissolved, weighed 2-fluoro-4-trifluoromethylbenzaldehyde (234mg, 1.22mmol) into the above reaction system, continued to heat and reflux for 2.5h, then cooled to room temperature, filtered, and used for filter cake Washed with absolute ethanol, and recrystallized from absolute ethanol to obtain 181 mg of a white solid with a yield of 87% and a melting point of 247.2-249.0°C. 1 H NMR (400MHz, DMSO-d 6 )δ12.34(s,1H),8.45-8.37(m,3H),8.24(dd,J 1 =7.6Hz,J 2 =7.6Hz, 1H), 7.79(d, J=10.8Hz, 1H), 7.69(d, J=8.4Hz, 1H), 3.97(s, 3H). 13 C NMR (100MHz, DMSO-d 6 ) δ 161.4, 158.9, 156.3, 155.2, 154.0, 137.3, 134.4...

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Abstract

The invention discloses a compound shown in general formula I and an application thereof as a plant disease-resistant activator, wherein R1 is independently selected from hydrogen, C1-C6 alkyl, C1-C6 halogenated alkyl, C3-C6 naphthenic base, halogen, nitro and hydroxyl; R2 is independently selected from C1-C6 alkyl, C1-C6 halogenated alkyl, hydroxyl, C1-C6 alkoxy, C1-C6 halogenated alkoxy, substituted or unsubstituted C6-C14 aryl, halogen, nitro, amino, C1-C6 alkoxy, carboxyl, C1-C3 alcoxyl formyl and pentabasic or hexahydric nitrogen and heterocyclic ring of oxygen or sulfur-containing; n is selected from 0-5. The compound is used for inhibiting the pathogens through inducing the plants to generate disease resistance, rather than directly killing or inhibiting the pathogens; the compound has the advantages of systematicness, long-lasting effect, broad spectrum and safety, so that the dosage of highly toxic pesticide can be reduced, and environment friendliness, great industrial / commercial prospect and market value are achieved.

Description

technical field [0001] The invention relates to the field of agricultural science and technology. Specifically, the present invention relates to the heterocyclic compound represented by formula I and its application in inducing plants to produce anti-insect activity. Background technique [0002] Pesticides mainly refer to chemical drugs used to prevent various diseases (pests, pests, nematodes, pathogens, weeds and rodents) and regulate plant growth in agricultural, forestry and animal husbandry production. Before the 1980s, pesticides were mainly used to "kill" pests, but since the 1980s, the concept of pesticides has undergone great changes. Today, people focus less on "killing" and more on conditioning. Therefore, the purpose of modern pesticides is to effectively control insect pests and bacteria, and to be safe to non-target organisms and the environment. [0003] Pesticides have a long history of about 150 years of development in the world. In the 1970s and 1980s, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A01N43/90A01P1/00A01P3/00
CPCA01N43/90C07D487/04
Inventor 徐玉芳赵振江朱维平李洪林李鹏飞李宝聚石延霞钱旭红
Owner EAST CHINA UNIV OF SCI & TECH
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