CN105541632B - The imperial saliva flores aurantii ester bactericide of one kind drop - Google Patents
The imperial saliva flores aurantii ester bactericide of one kind drop Download PDFInfo
- Publication number
- CN105541632B CN105541632B CN201510866407.7A CN201510866407A CN105541632B CN 105541632 B CN105541632 B CN 105541632B CN 201510866407 A CN201510866407 A CN 201510866407A CN 105541632 B CN105541632 B CN 105541632B
- Authority
- CN
- China
- Prior art keywords
- flores aurantii
- imperial saliva
- compound
- aurantii ester
- drop
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- XWPRKOUKBYLKPF-IHETXDGRSA-N CC(C)(CCC1)[C@H](CC2)[C@@]1(C)[C@@H](CC(O)=O)[C@]2(C)OC(C)=O Chemical compound CC(C)(CCC1)[C@H](CC2)[C@@]1(C)[C@@H](CC(O)=O)[C@]2(C)OC(C)=O XWPRKOUKBYLKPF-IHETXDGRSA-N 0.000 description 1
- IQRPSJPFBMWAQI-OYRXZESESA-N CC(C)(CCC1)[C@H](CC2)[C@@]1(C)[C@@H](CC(OC/C=C(/C)\CCC=C(C)C)=O)[C@]2(C)OC(C)=O Chemical compound CC(C)(CCC1)[C@H](CC2)[C@@]1(C)[C@@H](CC(OC/C=C(/C)\CCC=C(C)C)=O)[C@]2(C)OC(C)=O IQRPSJPFBMWAQI-OYRXZESESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a kind of imperial saliva flores aurantii ester of new compound drop, particular chemical formula is shown below：
Description
Technical field
The present invention relates to a kind of application of new compound and the compound in the agriculture germ of preventing and treating.
Background technology
It is unique, low to people, animal and natural enemy to the target organismses selectively good, mode of action that plant source natural product agricultural chemicals has
Malicious the features such as.But it is due to that most natural products activity are undesirable, and limited source, it is seriously limited in agricultural production
Extensive use.Structure optimization is carried out by guide of plant source natural product, its bioactivity is improved, and then develop novel green agriculture
Medicine, is an important directions of New pesticides discovery all the time.
Sclareol has preventing and treating soybean rust, wheat powdery mildew, coordinate plant growth and plant defense function, is one
Lead compound with potential Development volue.At present, sclareol exploitation is Pesticidal products by external rarely seen Japanese Scientists
In addition, it yet there are no the successful report of its derivative research and development.Based on above reason, using chemical synthesis process, synthesize
Sclareol analogue, and more systematic research is carried out to its bactericidal activity, insecticidal activity and activity of weeding, make every effort to therefrom send out
The higher secondary lead compound of existing activity, so as to be further research and development sclareol based theoretical.
Above formula is sclareol
The content of the invention
An object of the present invention is the open imperial saliva flores aurantii ester of compound drop, and structure is as follows：
The two of the object of the invention are application of the open above-claimed cpd in the agriculture germ of preventing and treating.
It is demonstrated experimentally that the compound of the present invention has obvious bactericidal activity, there is direct chemical prevention to agriculture germ
Effect, can be prepared as agriculture germ control agent.
The medicine of the agriculture germ of preventing and treating by active component of the compounds of this invention falls within protection scope of the present invention.
When needing, acceptable carrier in one or more pesticidal preparations can also be added in the medicine,
The carrier includes diluent conventional in pesticidal preparations, excipient, filler, adhesive, wetting agent, sorbefacient, table
Face activating agent, lubricant, stabilizer etc..The formulation for the medicine being made is also various, can be pulvis, emulsion, aqua,
Granula etc..
Embodiment
The preparation of imperial saliva flores aurantii ester drops in embodiment 1.
Synthetic route is shown below：
Imperial sialic acid is dropped into 1.55g (5mmol) A acetyl hydroxyl and 0.93g (6mmol) B nerols are added to tri- mouthfuls of burnings of 50mL
In bottle, then weigh 1.15g (6mmol) 1- (3- dimethylamino-propyls) -3- ethyl carbodiimides (EDCI) and 0.12g (1mmol)
DMAP (DMAP) is added thereto, and is added 20mL dichloromethane, is heated to 40 DEG C of return stirring 48h.Afterwards by temperature
Near room temperature is spent, 12mL 10%H are added2SO4Solution, point liquid, organic phase is successively with appropriate saturation NaHCO3, saturation NaCl solution
Washing, revolving, column chromatographic isolation and purification (petroleum ether: ethyl acetate=15: 1), obtains white crystal 1.92g, yield 86.1%.
Product is levied by nucleus magnetic hydrogen spectrum and nuclear-magnetism carbon stave.
1H NMR (300MHz, CDCl3)δ：0.76 (6H, s, 2Me-4), 4.53-4.55 (2H, m, O-CH2), 4.98-5.07
(1H, m, C=CH), 5.31-5.36 (1H, m, C=CH)
13C NMR (75MHz, CDCl3)δ：173.8,169.5,141.9,131.7,123.1,118.8,85.8,60.6,
54.7,54.5,41.1,38.5,38.2,38.1,32.8,32.6,31.7,30.0,26.2,25.2,23.0,22.2,20.9,
19.5,19.3,17.8,17.2,15.2.
Bioactivity of the compounds of this invention of embodiment 2. to agriculture germ
Under aseptic condition, positive control Bravo and the gained compound of embodiment 1 1mL DMF are dissolved, sterilizing is added
It is stand-by that running water is diluted to 10mg/mL.
Using containing toxic medium method.
First, pastille culture medium is prepared.Each 2mL of decoction medicament configured is taken, 200mL is transferred to sterilized and be cooled to
In 45 DEG C or so of PDA culture medium, fully mix, pour into culture dish.Often processing is repeated 3 times, to add the culture of sterilized water
Base is control.
Secondly, transposing bacteria cake.Colony edge with card punch along test bacterium beats bacteria cake, with tweezers or connects acicula and takes bacteria cake,
Bacterium is connected to toxic culture medium center downwards, per one piece of ware.It is put into insulating box, is subsequently placed at 24~16 DEG C, after cultivates 2 days
From crossing method measurement, record colony diameter, inhibiting rate is calculated by below equation.
Test strain：Botrytis cinerea pers (Botrytis cinerea), fusarium graminearum (Fusarium
Graminearum), Rhizoctonia solani Kuhn (Rhizoctonia solani), tobacco brown spot pathogen (Alternaria
alternata)。
Bravo is equal to the inhibiting rate of botrytis cinerea pers, fusarium graminearum, Rhizoctonia solani Kuhn, tobacco brown spot pathogen
For 100%；The imperial saliva flores aurantii ester of drop to botrytis cinerea pers, fusarium graminearum, Rhizoctonia solani Kuhn, tobacco brown spot pathogen suppression
Rate processed is respectively 50%, 57.6%, 43.2%, 34.4%.
As a result show, at the concentration tested, compound of the invention is to agriculture germ botrytis cinerea pers, wheat scab
Bacterium, Rhizoctonia solani Kuhn, tobacco brown spot pathogen have obvious inhibition.Preliminary activation test result shows, the compound
With applications well prospect, it is expected to turn into a class novel agricultural germ controlling agent.
Claims (1)
1. a kind of imperial saliva flores aurantii ester of compound drop, particular chemical formula is as follows：
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510866407.7A CN105541632B (en) | 2015-12-03 | 2015-12-03 | The imperial saliva flores aurantii ester bactericide of one kind drop |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510866407.7A CN105541632B (en) | 2015-12-03 | 2015-12-03 | The imperial saliva flores aurantii ester bactericide of one kind drop |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105541632A CN105541632A (en) | 2016-05-04 |
| CN105541632B true CN105541632B (en) | 2017-10-13 |
Family
ID=55821251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510866407.7A Expired - Fee Related CN105541632B (en) | 2015-12-03 | 2015-12-03 | The imperial saliva flores aurantii ester bactericide of one kind drop |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105541632B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115160159B (en) * | 2022-03-21 | 2023-06-16 | 贵州大学 | Halichonin B analogue, preparation method thereof and application thereof in preparing agricultural bactericide |
-
2015
- 2015-12-03 CN CN201510866407.7A patent/CN105541632B/en not_active Expired - Fee Related
Non-Patent Citations (2)
| Title |
|---|
| Gd(OTf)3-catalyzed synthesis of geranyl esters for the intramolecular radical cyclization of their epoxides mediated by titanocene(III);William H. Garcia Santos et al;《Organic & Biomolecular Chemistry》;20141118;第13卷;第1358-1366页 * |
| 香紫苏醇衍生物的合成及其杀菌活性初步研究;白红进等;《西北农业学报》;20051231;第14卷(第2期);第64-68页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105541632A (en) | 2016-05-04 |
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| C06 | Publication | ||
| PB01 | Publication | ||
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| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20171013 Termination date: 20181203 |