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4-bromomethyl-5,7-dihydroxy-benzopyran-2-one and synthetic method thereof and agricultural biological activity

A technology of benzopyran and bromomethyl, which is applied in the field of coumarin compound and its preparation and application, can solve the problems of synthesis method and agricultural bactericidal activity that have not been reported in the literature, and achieve good inhibitory or killing effect

Inactive Publication Date: 2013-02-27
QINGDAO AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Confirmed by the China Chemical Industry Information Center, the patent involves the compound 4-bromomethyl-5,7-dihydroxy-benzopyran-2-one is a new compound that has not been reported in the literature, its synthesis method, agricultural fungicidal activity, etc. None of them have been reported in the literature, and they are novel

Method used

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  • 4-bromomethyl-5,7-dihydroxy-benzopyran-2-one and synthetic method thereof and agricultural biological activity
  • 4-bromomethyl-5,7-dihydroxy-benzopyran-2-one and synthetic method thereof and agricultural biological activity

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Embodiment Construction

[0014] Typical preparation of compounds:

[0015]

[0016] In 20ml of benzene, add 0.0143g of benzoyl peroxide, 1.0g of N-bromosuccinimide and 1.0g of 5,7-dihydroxy-4-methylcoumarin, heat to reflux for 72h, evaporate to dryness Solvent, hot water washing, petroleum ether - acetone recrystallization to obtain white crystals. Melting point: 203-205°C.

[0017] NMR data ( 1 H, 13 C, DEPT, GCOSY, GHSQC, GHMBC-NMR; 600MHz; internal standard TMS; solvent CD 3 COCD 3 )as follows:

[0018] δppm 2.56 (2H, d), 5.83 (1H, d), 6.28 (1H, d), 6.36 (1H, d), 9.14 (1H, S), 9.40 (1H, S); 23.9 (secondary carbon), 96.0 (tertiary carbon), 100.0(tertiary carbon), 103.6(quaternary carbon), 110.6(tertiary carbon), 155.4(quaternary carbon), 158.0(quaternary carbon), 158.5(quaternary carbon), 160.8(quaternary carbon), 161.8(quaternary carbon) carbon)

[0019] Typical determination of pesticide (bactericidal) activity:

[0020] Take a certain amount of the prepared medicine solution and place...

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Abstract

The invention (4-bromomethyl-5, 7-dihydroxy-chromene -2-ketone, a synthesis method thereof and the agricultural biological activity thereof) relates to a coumarin compound and preparation and application thereof. The compound can be prepared by bromination of the 4-bromomethyl-5, 7-dihydroxy-chromene -2-ketone through N-bromosuccinimide, has good antibiotic activity on various agricultural plant pathogens such as fruit white rot of grapes, ring rot of apple, blight of cotton, canker of apple fruit and so on, and simultaneously has certain inhibition effect on a plurality of kinds of insects and weed.

Description

technical field [0001] The invention relates to a coumarin compound (4-bromomethyl-5,7-dihydroxy-benzopyran-2-one) and its preparation and application, specifically relating to the fields of agricultural sterilization, insecticide and herbicide . Background technique [0002] Shandong Agricultural Biomimetic Application Engineering Technology Research Center of Qingdao Agricultural University started the research on the agricultural bactericidal activity of figs in 1999. Under the tracking of bactericidal activity, the antibacterial lead compound psoralen was isolated from fig leaves, and psoralen was used as the lead The compound was modified by biomimetic synthesis method, several derivatives were synthesized, and their agricultural bactericidal and antibacterial activities were determined. The compound 4-bromomethyl-5,7-dihydroxy-benzopyran-2-one (4-bromomethyl-5,7-dihydroxy-coumarin) was found to be effective against grape white rot and apple ring A variety of agricult...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/08C07D311/16A01N43/16A01P3/00A01P7/00A01P13/00
Inventor 孟昭礼郝双红魏艳厉建燕
Owner QINGDAO AGRI UNIV