CN101381357B - 4-bromomethyl-5,7-dihydroxy-benzopyran-2-one and synthetic method thereof and agricultural biological activity - Google Patents
4-bromomethyl-5,7-dihydroxy-benzopyran-2-one and synthetic method thereof and agricultural biological activity Download PDFInfo
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- CN101381357B CN101381357B CN 200710149905 CN200710149905A CN101381357B CN 101381357 B CN101381357 B CN 101381357B CN 200710149905 CN200710149905 CN 200710149905 CN 200710149905 A CN200710149905 A CN 200710149905A CN 101381357 B CN101381357 B CN 101381357B
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- bromomethyl
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Abstract
The invention (4-bromomethyl-5, 7-dihydroxy-chromene -2-ketone agricultural biological activity) 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 (cabbage caterpillar, aphid and the like) and weed (amaranthus retroflexus, crab grass and the like).
Description
Technical field
The present invention is a kind of coumarin compound (4-brooethyl-5,7-dihydroxyl-chromen-2-one) and preparation and application thereof, is specifically related to agricultural bactericidal, desinsection and weedicide field.
Background technology
Qingdao Agricultural University's Agriculture in Shandong Province Bionics application Engineering Technical Research Centre was since Fructus Fici agricultural bactericidal activity research in 1999, under fungicidal activity is followed the tracks of, from common fig leaf juice, isolate antibacterial lead compound psoralene, take psoralene as lead compound, adopt bionical synthetic method that its chemical structure is transformed, synthesize several derivatives, and measured their agricultural bactericidal bacteriostatic activity.Find compound 4-brooethyl-5,7-dihydroxyl-chromen-2-one (4-brooethyl-5,7-dihydroxyl-tonka bean camphor) the various agricultural phytopathogens such as fruit white rot of grape bacterium, Botryosphaeria berengeriana f. sp, cotton-wilt fusarium, Valsa mali is had preferably bacteriostatic activity, simultaneously various pests and weeds are also had certain restraining effect.
Look into new conclusive evidence through China Chemical Information Center, patent relates to compound 4-brooethyl-5, and 7-dihydroxyl-chromen-2-one is the new compound that has no bibliographical information, and its synthetic method, agricultural bactericidal activity etc. is showed no bibliographical information, has novelty.
Summary of the invention
The object of the present invention is to provide a kind of new coumarin compound and preparation method thereof, it can be applicable to agricultural upper disease, insect pest and crop smothering with the control crop.
Technical scheme of the present invention is as follows:
The invention provides a kind of coumarin compound, its name is called 4-brooethyl-5,7-dihydroxyl-chromen-2-one (4-brooethyl-5,7-dihydroxyl-tonka bean camphor), and structural formula is as follows,
This compound can prepare in appropriate solvent like this, and with suitable catalyst, under illumination, but the N-bromo-succinimide reacts certain hour bromination intermediate product 4-methyl-5 under suitable temp, and the 7-dihydroxycoumarin processes namely getting the purpose product.
The optional benzene,toluene,xylene of appropriate solvent, tetracol phenixin, chloroform, phosgene, 1,2-ethylene dichloride, chlorobenzene etc.
The suitable optional benzoyl peroxide of catalyzer, tetramethyl plumbane, peroxidation uncle butyl ether, azo-compound etc.
Proper temperature refers to room temperature to the solvent boiling point temperature, is generally 20-200 ℃.
Reaction times is 1 hour to 108 hours.
Compound of the present invention has good inhibition or lethal effect to various agricultural plant pathogenic fungi, bacterium, virus, nematode, insect, evil mite, weeds etc.
Embodiment
Typical case's preparation of compound:
In 20ml benzene, add the 0.0143g benzoyl peroxide, 1.0g N-bromo-succinimide and 1.0g 5,7-dihydroxyl-4-methylcoumarin, heating reflux reaction 72h, solvent evaporated, hot water wash, sherwood oil-acetone recrystallization gets white crystal.Fusing point: 203-205 ℃.
Nuclear magnetic data (
1H,
13C, DEPT, GCOSY, GHSQC, GHMBC-NMR; 600MHz; Interior mark TMS; Solvent C D
3COCD
3) as follows:
δ ppm 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 carbons), 100.0 (tertiary carbons), 103.6 (quaternary carbons), (110.6 tertiary carbon), 155.4 (quaternary carbons), 158.0 (quaternary carbons), (158.5 quaternary carbon), 160.8 (quaternary carbons), 161.8 (quaternary carbons)
Agricultural chemicals (sterilization) active typical case measure:
Get a certain amount of liquid for preparing and place 60 ℃ of left and right sides of 100ml PDA sterilising medium, shake up, pour in the sterilization culture dish of diameter 60mm, after the cooled and solidified, moving respectively delivers a child grows unanimously, diameter is the bacterium cake of 4mm, as blank, 3 repetitions are established in every processing with the sterilising medium that adds the equivalent coordinative solvent.After putting into 25 ℃ of constant incubators cultivation certain hours, measure colony diameter, calculate bacteriostasis rate, ask for 50 1.143851e-144ffective concentration EC
50As: to the EC of apple anthrax bacteria
50Be 12.7ppm, to the EC of Botryosphaeria berengeriana f. sp
50Be 21.4ppm.
Claims (1)
1. the application of coumarin compound germ on the control crop, wherein said coumarin compound is 4-brooethyl-5,7-dihydroxyl-chromen-2-one.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200710149905 CN101381357B (en) | 2007-09-04 | 2007-09-04 | 4-bromomethyl-5,7-dihydroxy-benzopyran-2-one and synthetic method thereof and agricultural biological activity |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200710149905 CN101381357B (en) | 2007-09-04 | 2007-09-04 | 4-bromomethyl-5,7-dihydroxy-benzopyran-2-one and synthetic method thereof and agricultural biological activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101381357A CN101381357A (en) | 2009-03-11 |
| CN101381357B true CN101381357B (en) | 2013-02-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200710149905 Expired - Fee Related CN101381357B (en) | 2007-09-04 | 2007-09-04 | 4-bromomethyl-5,7-dihydroxy-benzopyran-2-one and synthetic method thereof and agricultural biological activity |
Country Status (1)
| Country | Link |
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| CN (1) | CN101381357B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102217597A (en) * | 2011-04-21 | 2011-10-19 | 南开大学 | Application of 3-benzoyl-4-hydroxycoumarin derivative in agricultural sterilization |
| CN104351179B (en) * | 2014-08-12 | 2016-03-02 | 青岛农业大学 | The Ag-fungicidal Activity of 8-phenyl (isopropyl) coumarin |
| CN105218530B (en) * | 2015-10-20 | 2019-07-02 | 青岛农业大学 | 3- (1- aryl -2- (2- azepine aromatic hydrocarbons) ethyl) -4 hydroxy coumarin and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1869032A (en) * | 2005-05-26 | 2006-11-29 | 沈阳化工研究院 | Coumarin kind compound and its preparation and application |
-
2007
- 2007-09-04 CN CN 200710149905 patent/CN101381357B/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1869032A (en) * | 2005-05-26 | 2006-11-29 | 沈阳化工研究院 | Coumarin kind compound and its preparation and application |
Non-Patent Citations (1)
| Title |
|---|
| Ramiandrasoa, F.Preparation of 4-(a-hydroxyalkyl)coumarins, models of natural insecticides..《Bull. Soc. Chim. Fr.》.1987,(第1期),177-180. * |
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| CN101381357A (en) | 2009-03-11 |
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