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Preparation and usage of unnatural 3,4-dihydro isocoumarin derivatives

A technology of isocoumarins and derivatives, applied in 3 fields, can solve problems such as relatively few reports of biological activity

Inactive Publication Date: 2007-10-31
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Many compounds in the isocoumarin derivatives disclosed in domestic and foreign patent documents have important physiological and biological activities, and coumarin compounds have been used as pesticides such as rodenticides and herbicides. There are many patents on the synthesis of derivatives of cyanide, but there are relatively few reports on biological activity, especially the biological activity of pesticides. The present invention converts 3,4-dihydro derivatives based on the synthesis of isocoumarin in the previous stage, and treats these Compounds are tested for relevant biological activity in order to be able to detect their pesticides such as herbicidal, insecticidal, fungicidal and other plant disease control activities

Method used

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  • Preparation and usage of unnatural 3,4-dihydro isocoumarin derivatives
  • Preparation and usage of unnatural 3,4-dihydro isocoumarin derivatives
  • Preparation and usage of unnatural 3,4-dihydro isocoumarin derivatives

Examples

Experimental program
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Effect test

Embodiment 1

[0033] (31B) Synthesis and structure identification of 2-(3′,5′-phenacylmethyl)benzoic acid:

[0034] Dissolve 3-(3 ', 5'-dichlorophenyl) isocoumarin ( 9.0 g, 30 mmol) (31A), refluxed for 4 hours, after cooling, ethanol was removed under reduced pressure. Add cold water (20 ml) to the reaction mixture, acidify with dilute hydrochloric acid, extract 3 times with 20 ml of dichloromethane, dry over anhydrous sodium sulfate, distill off the solvent under reduced pressure to obtain a crude product, recrystallize with methanol to obtain 2-(3 ', 5'-dichlorophenacyl) benzoic acid (31B) pure product 6.5g, 21.1 mmoles, measure melting point and 1 H NMR, its chemical structural formula and physical and chemical parameters are shown in Table 1 and Table 2, as seen from Table 1 and Table 2, this compound 1 H NMR shows the chemical shift corresponding to its structure, the number of H is consistent with its structure, and MS measurement shows the corresponding M + The m / z peak of the IR ...

Embodiment 2

[0036] Synthesis and structure identification of 2-(2′,3′-dichlorophenacyl)benzoic acid (32B):

[0037] Dissolve 3-(2 ', 3'-dichlorophenyl) isocoumarin (8.8 g, 30 mmol) in a 100 ml three-necked flask with ethanol (50 ml) and potassium hydroxide (5%, 100 ml) (32A), refluxed for 4 hours, after cooling, ethanol was removed under reduced pressure. Add cold water (20 ml) to the reaction mixture, acidify with dilute hydrochloric acid, extract 3 times with 20 ml of dichloromethane, dry over anhydrous sodium sulfate, distill off the solvent under reduced pressure to obtain a crude product, recrystallize with methanol to obtain 2-(2 ', 3'-dichlorophenacyl) benzoic acid (32B) pure product 6.8g, 22.0 mmoles, measure melting point and 1 H NMR, its chemical structural formula and physical and chemical parameters are shown in Table 1 and Table 2, as seen from Table 1 and Table 2, this compound 1 H NMR shows the chemical shift corresponding to its structure, the number of H is consistent w...

Embodiment 3

[0039] Synthesis and structure identification of 2-(2′,5′-dichlorophenacyl)benzoic acid (33B):

[0040] Dissolve 3-(2′,3′-dichlorophenyl)isocoumarin (9.0g, 30mmol) in a 100ml three-necked flask with ethanol (50ml) and potassium hydroxide (5%, 100ml) (32A), refluxed for 4 hours, after cooling, ethanol was removed under reduced pressure. Add cold water (20 ml) to the reaction mixture, acidify with dilute hydrochloric acid, extract 3 times with 20 ml of dichloromethane, dry over anhydrous sodium sulfate, distill off the solvent under reduced pressure to obtain a crude product, recrystallize with methanol to obtain 2-(2 ', 5'-dichlorophenacyl) benzoic acid (33B) pure product 6.3g, 20.5 mmoles, measure melting point and 1 H NMR, its chemical structural formula and physical and chemical parameters are shown in Table 1 and Table 2, as seen from Table 1 and Table 2, this compound 1 H NMR shows the chemical shift corresponding to its structure, the number of H is consistent with its ...

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Abstract

The invention discloses a synthetic method of non-natural 3, 4- dihydro-isocoumarin derivant and intermediate compound and usage in agricultural chemicals domain, which is characterized by the following: possessing chemical constitution general formula as follow; comprising six 3, 4- dihydro-isocoumarin derivant (C series). This invention discloses the synthetic method of this compound, usage and purposes.

Description

technical field [0001] The technical scheme of the present invention relates to halogen-substituted 3,4-dihydroisocoumarin derivatives, in particular to a synthesis method, a use method and an application of 3,4-dihydroisocoumarin derivatives. Background technique [0002] Isocoumarin (scientific name: 1H-2-benzopyran-1-one) is the basic structure of some natural products and widely exists in nature. Its derivatives have a wide range of physiological and biological activities such as antibacterial, anti-inflammatory, anti-cancer, Inhibition of protease and herbicide, etc. and obvious anticancer activity (Li Li et al., Journal of Nanjing Normal University (Engineering Technology Edition), 2005, 5(2):64-67.). Isocoumarin and 3,4-dihydroisocoumarin are secondary metabolites of fungi, mosses, molds, bacteria, higher plants and animals. , Penicillium, Streptomyces and other species isolated. They are also components of higher plants such as Kapokceae, Asteraceae, Fabaceae, Myri...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/76A01N43/16A01P3/00A01P13/00
Inventor 范志金瓜勒姆·瓜弟尔那斯姆·汗山·拉姆
Owner NANKAI UNIV
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