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Phenalide hydrazide compound as well as preparation method and application thereof

A technology of phthalide hydrazides and compounds, which is applied in the field of phthalide hydrazide compounds and their preparation, and can solve problems such as gaps in antibacterial activity

Pending Publication Date: 2022-08-02
GUIZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

León A., Del- M., J.L., Delgado G.Phthalides: distribution in nature, chemical reactivity, synthesis, and biological activity [J]. Progress in the Chemistry of Organic Natural Products, 2017, 104:127-246 and other literatures reported the extraction of natural phthalides from plants -Butylphthalide not only has the effect of treating cardiovascular and cerebrovascular diseases, but also has a certain activity of inhibiting plant pathogenic fungi, but its antibacterial activity has a significant gap compared with commercial fungicides

Method used

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  • Phenalide hydrazide compound as well as preparation method and application thereof
  • Phenalide hydrazide compound as well as preparation method and application thereof
  • Phenalide hydrazide compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Preparation of 1-butyl-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile (formula III)

[0052] Under nitrogen protection, compound of formula II, 6-bromo-3-butylisobenzofuran-1(3H)-one (2.5 g, 9.3 mmol) and cuprous cyanide (2.0 g, 14 mmol) were dissolved in N-methyl pyrrolidine (NMP, 10 mL), and reacted at 180 °C for 3 h. After the reaction was completed, the reaction solution was cooled to room temperature, 50 mL of water was added, extracted with ethyl acetate (50 mL × 3), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. After recrystallization from ethyl acetate, 1.0 g of a white solid compound of formula III was obtained in a yield of 50.0%, m.p. 82-83°C. 1 HNMR (600MHz, CDCl 3 )δ8.19(d,J=1.2Hz,1H),7.95(dd,J=8.4,1.2Hz,1H),7.61(d,J=7.8Hz,1H),5.56-5.54(m,1H), 2.11-2.05(m, 1H), 1.82-1.76(m, 1H), 1.52-1.36(m, 4H), 0.93(t, J=7.2Hz, 3H); 13 C NMR (150MHz, CDCl 3 )δ168.2,153.8,137.0,129.9,127.5,123.1,117.3,113.7,81.5,34.1,26.8,22.3,13.8; HRMS(...

Embodiment 2

[0054] Preparation of 1-butyl-3-oxo-1,3-dihydroisobenzofuran-5-carboxylic acid (formula IV)

[0055] Under nitrogen protection, compound formula III (1.0 g, 4.65 mmol) was dissolved in 98% H 2 SO 4 (2.5mL), add H at 0°C 2 O (2.5mL), stirred at room temperature for 0.5h, then moved to 100°C oil bath for reflux reaction for 24h, after the reaction was complete, poured the reaction solution into 20mL of water, extracted with ethyl acetate (50mL×3), dried over anhydrous sodium sulfate, reduced After being concentrated under pressure, recrystallized from ethyl acetate to obtain 0.71 g of a white solid compound of formula IV, yield 65.1%, m.p. 145-147°C. 1 H NMR (600MHz, DMSO-d 6 )δ9.10(d,J=7.8Hz,1H),9.04(s,1H),8.62(d,J=7.8Hz,1H),6.53-6.51(m,1H),2.96-2.86(m,1H) ), 2.54-2.49(m, 1H), 2.14-2.03(m, 4H), 1.66(t, J=6.6Hz, 3H); 13 C NMR (150MHz, DMSO-d 6 )δ169.5,166.6,154.6,135.3,132.5,126.4,126.0,123.6,81.8,33.6,26.9,22.3,14.2;HRMS(ESI)calcd for C 13 H 15 O 4 [M+H] + m / z: 235.09...

Embodiment 3

[0057] Preparation of arylhydrazinephthalide compounds (formula V):

[0058] Under nitrogen protection, the compound of formula IV (80 mg, 0.34 mmol) was dissolved in thionyl chloride (2 mL), and the reaction was refluxed for 8 h. TLC detected that the reaction was completed. The reaction solution was concentrated and dissolved in dry tetrahydrofuran for later use; another In a 10 mL double-necked flask, the aryl hydrazine hydrochloride compound (0.2 mmol) was dissolved in dry pyridine (2 mL), slowly dropped into the above tetrahydrofuran solution at 0°C, and the reaction was carried out at room temperature for 1 h. TLC detected the completion of the reaction. It was poured into 20 mL of water, extracted with dichloromethane (20 mL×3), dried over anhydrous sodium sulfate, concentrated and recrystallized from ethyl acetate to obtain compound formula V. Specific compounds are shown in Table 1.

[0059] Table 1 When R 1 When it is butyl, the specific compound formula V

[0060...

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Abstract

The invention belongs to the technical field of pesticides, and particularly relates to a phthalide hydrazide compound as well as a preparation method and application thereof. The phthalide hydrazide compound prepared by the invention has good bacteriostatic activity, and when the phthalide hydrazide compound is used as an active component in preparation of a bactericide, plant diseases caused by plant pathogenic fungi can be prevented and treated; the bactericidal composition is used for preventing and treating plant diseases caused by alternaria alternata, pyricularia grisea, phytophthora capsici, watermelon fusarium wilt, potato dry rot, sclerotinia sclerotiorum, valsa mali, botrytis cinerea, alternaria brassicae and fusarium graminearum.

Description

technical field [0001] The invention belongs to the technical field of pesticides, and in particular relates to a phthalide hydrazide compound, a preparation method and application thereof. Background technique [0002] Plant diseases are natural disasters that seriously endanger agricultural production and are difficult to control. They will not only reduce crop yield and quality, but also cause many pathogenic fungi that are carcinogenic, neurotoxic or teratogenic during the growth and metabolism of some pathogenic fungi in the host. A variety of secondary metabolites (such as aflatoxin and zearalenone, etc.), a serious threat to human and animal health and safety. Therefore, in recent years, various pesticide companies have developed and developed a variety of fungicides with broad spectrum and high activity. These chemical fungicides play a pivotal role in ensuring agricultural production and human life. However, long-term reliance and extensive use of The problems of p...

Claims

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Application Information

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IPC IPC(8): C07D405/12C07D307/88A01N43/40A01N43/38A01P3/00
CPCC07D405/12C07D307/88A01N43/40A01N43/38Y02A50/30
Inventor 樊玲玲李永罗忠福汤磊
Owner GUIZHOU MEDICAL UNIV
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