CN109928880A - A kind of purple perilla Epoxide carbonyl ethyl propionate and its application - Google Patents
A kind of purple perilla Epoxide carbonyl ethyl propionate and its application Download PDFInfo
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- CN109928880A CN109928880A CN201910272106.XA CN201910272106A CN109928880A CN 109928880 A CN109928880 A CN 109928880A CN 201910272106 A CN201910272106 A CN 201910272106A CN 109928880 A CN109928880 A CN 109928880A
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- ethyl propionate
- purple perilla
- epoxide carbonyl
- carbonyl ethyl
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Abstract
The present invention relates to antifungals to sterilize field, specifically discloses a kind of purple perilla Epoxide carbonyl ethyl propionate and its application, the purple perilla Epoxide carbonyl ethyl propionate particular chemical formula are shown below:
Description
Technical field
The present invention relates to antifungals to sterilize field, and in particular to a kind of new compound purple perilla Epoxide carbonyl propionic acid second
Ester and its application.
Background technique
As China's agricultural economy is gradually changed from extensive mode of growth to intensive style, farming industry emerges rapidly
With develop, become " the two industries Ji " in the agriculture process of reproduction.Agricultural product especially fresh and live agricultural product, water content is high,
It is full of nutrition, it easily rots, if carrying out sterilization processing not in time in postpartum, commodity property is difficult to protect in the circulation process
It holds, easily occurs largely to rot, cause heavy losses.The agricultural output in China especially fruits and vegetables yield has been in generation at present
Boundary tops the list, but the agricultural product that China produces every year are from farmland to dining table, and loss late is up to 25%~30%, and developed country
Crop loss rate then generally control 5% hereinafter, its main cause is that agricultural products in China postpartum sterilization technology is more conservative
With backwardness.It is found in investigation simultaneously, currently used postpartum sterilization dosage form includes the pesticides such as carbendazim, benomyl, probenazole, is deposited
In the risk of secondary pollution,
Perilla alcohol is to be naturally present in citrus in the form of free state or ester, cherry, peppermint, bergamot, ginger grass, miscellaneous smoke clothing
Small-molecule substance in the various plants such as grass is the monoterpene of plant formaldehyde, the generation of valeric acid metabolic pathway.Perilla alcohol has
Bactericidal effect is the fungicide of a kind of pair of human security.Perilla alcohol has been authenticated by U.S. FDA as food additives.With
Research go deep into, perilla alcohol is in fields such as medicine, fragrance, daily cosmetics using increasingly extensive.Perilla alcohol is a tool
There is the lead compound of potential Development volue, the structure based on perilla alcohol, design synthesis perilla alcohol derivant, and work is sterilized to it
Property is studied, and is the important channel for obtaining higher Fungicidal active compound.
Summary of the invention
An object of the present invention is open compound purple perilla Epoxide carbonyl ethyl propionate, structure as shown in formula:
The second object of the present invention is application of the open above compound in agricultural product postpartum fungicide.
It is demonstrated experimentally that the compound of the present invention has apparent bactericidal activity, have to agricultural product postpartum germ direct anti-
Effect is controlled, agricultural product postpartum fungicide can be prepared as.
Protection scope of the present invention is also belonged to by the drug of the agriculture germ of the prevention and treatment of active constituent of the compounds of this invention.
When needed, acceptable carrier in one or more fungicide, institute can also be added in the drug
Stating carrier includes excipient conventional in fungicide, diluent, filler etc., and the dosage form of manufactured drug is also multiplicity, can
To be pulvis, aqua, granule etc..
The germ being previously mentioned in application or drug in the present invention is penicillium expansum, pseudomonas and the pathogen of Botrytis cinerea.
The present invention has the beneficial effect that:
The present invention provides a kind of with efficient sterilizing effect and to the purple perilla Epoxide carbonyl ethyl propionate of human security, should
Compound especially has direct, good control efficiency to agricultural product postpartum germ, can be prepared as agricultural product postpartum fungicide,
There is practical application value in agricultural production.
Specific embodiment
The present invention is further elaborated combined with specific embodiments below, but the present invention is not limited to following embodiments.Institute
State method is conventional method unless otherwise instructed.The material can be gotten from open business unless otherwise instructed.
The preparation of embodiment 1, purple perilla Epoxide carbonyl ethyl propionate
Synthetic route is shown below:
1.52g (10mmol) perilla alcohol, 4.86g (30mmol) carbonyl dimidazoles, 20mL tetrahydrofuran are added to 100mL
It in three-necked flask, is heated to reflux 3 hours, filters, successively use methylene chloride, water washing, anhydrous magnesium sulfate is dry, and revolving obtains white
Color dope is added in 50mL three-necked flask, adds 1.42g (12mmol) ethyl lactate, 20mL N, N- dimethyl formyl
Amine, 90 DEG C are stirred 6 hours.To entering into methylene chloride containing 50mL and 50mL water separatory funnel, liquid separation, organic phase washed with water,
Saturated sodium chloride solution washing, concentrated by rotary evaporation, column chromatographic isolation and purification obtain colourless liquid 2.16g, yield 73%.
Product is levied by nucleus magnetic hydrogen spectrum and nuclear-magnetism carbon stave.
1H NMR(300MHz,CDCl3) δ: 5.81 (s, 1H), 4.98 (q, J=7.1Hz, 1H), 4.71 (d, J=6.3Hz,
2H), 4.61-4.44 (m, 2H), 4.22 (q, J=7.1Hz, 2H), 2.15 (dd, J=17.5,4.0Hz, 4H), 2.05-1.78
(m,2H),1.73(s,3H),1.59–1.38(m,4H),1.33–1.18(m,3H).
13C NMR(75MHz,CDCl3)δ:170.43,154.49,149.40,131.83,126.90,108.77,72.35,
71.57,61.43,40.62,30.38,27.16,26.15,20.69,16.93,14.04.
Embodiment 2, the compounds of this invention are to the bioactivity of agricultural product postpartum germ
Aseptically, perilla alcohol, positive control carbendazim and 1 gained compound of embodiment 1mL DMF are dissolved,
Aqua sterilisa is added and is diluted to 10mg/L, for use.
In penicillium expansum (Penicillium expansum), pseudomonas (Pseudomonas sp), the pathogen of Botrytis cinerea
The appropriate spore of picking, is inoculated in the PDA culture medium of sterilizing in the bacterial strain of (Botrytis cinerea), activates 8 days at 25 DEG C.
5mL sterile water is added in test tube, scrapes spore using aseptic inoculation ring, spore suspension is made.Draw 200 μ L spore suspensions
In on fresh PDA plate, 7 days are cultivated at 25 DEG C, for use.
It is cooling after PDA culture medium is dissolved, it is separately added into change obtained by 10mL 10mg/L perilla alcohol, carbendazim and embodiment 1
Close object solution, by the culture medium pour into diameter be 15mm culture medium, added with equivalent sterile water culture medium as blank pair
According to.
Aseptic card punch with diameter for 6mm is beaten respectively takes the penicillium expansum for having cultivated 7 days, pseudomonas, Botrytis cinerea
The fungus block of bacterium is placed in the above-mentioned culture dish center with medicament, cultivates at 25 DEG C, bacterial plaque diameter incrementss are measured after 3 days, calculate
Inhibiting rate.
Inhibiting rate=[(blank control bacterial plaque diameter incrementss-processing group bacterial plaque diameter incrementss)/blank control bacterial plaque is straight
Diameter incrementss] × 100%
Test result is shown in Table 1.
The bactericidal activity to agricultural product postpartum germ of 1. compound of table
Table 1 the result shows that, the compound of the present invention is to agricultural product postpartum germ penicillium expansum, pseudomonas, Botrytis cinerea
Bacterium all has remarkable inhibiting activity, and inhibiting rate has potential application 90% or more in agricultural product postpartum bacteria-treating
Prospect.
Although above having used general explanation, specific embodiment and test, the present invention is made to retouch in detail
It states, but on the basis of the present invention, it can be made some modifications or improvements, this is apparent to those skilled in the art
's.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to claimed
Range.
Claims (5)
1. a kind of purple perilla Epoxide carbonyl ethyl propionate, which is characterized in that particular chemical formula is shown below:
2. application of the purple perilla Epoxide carbonyl ethyl propionate described in claim 1 in agricultural product postpartum fungicide.
3. application according to claim 2, which is characterized in that germ is penicillium expansum, pseudomonas and the pathogen of Botrytis cinerea.
4. using purple perilla Epoxide carbonyl ethyl propionate described in claim 1 as the drug of active constituent.
5. drug according to claim 4, which is characterized in that germ is penicillium expansum, pseudomonas and the pathogen of Botrytis cinerea.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910272106.XA CN109928880B (en) | 2019-04-04 | 2019-04-04 | Perilla frutescens oxy carbonyl ethyl propionate and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910272106.XA CN109928880B (en) | 2019-04-04 | 2019-04-04 | Perilla frutescens oxy carbonyl ethyl propionate and application thereof |
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| CN109928880A true CN109928880A (en) | 2019-06-25 |
| CN109928880B CN109928880B (en) | 2021-08-31 |
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| CN201910272106.XA Active CN109928880B (en) | 2019-04-04 | 2019-04-04 | Perilla frutescens oxy carbonyl ethyl propionate and application thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111217708A (en) * | 2020-02-21 | 2020-06-02 | 中国林业科学研究院林产化学工业研究所 | Preparation method and weeding application of alkyl perillamine derivative |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5110832A (en) * | 1990-10-09 | 1992-05-05 | Doyle E. Chastain | Using perillyl alcohol to kill bacteria and yeasts |
| US5994598A (en) * | 1998-01-15 | 1999-11-30 | Doyle E. Chastain | Method of preparing perillyl alcohol and perillyl acetate |
| CN1458136A (en) * | 2003-06-17 | 2003-11-26 | 秦中 | Process for preparing high purity 1-perilla alcohol |
-
2019
- 2019-04-04 CN CN201910272106.XA patent/CN109928880B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5110832A (en) * | 1990-10-09 | 1992-05-05 | Doyle E. Chastain | Using perillyl alcohol to kill bacteria and yeasts |
| US5994598A (en) * | 1998-01-15 | 1999-11-30 | Doyle E. Chastain | Method of preparing perillyl alcohol and perillyl acetate |
| CN1458136A (en) * | 2003-06-17 | 2003-11-26 | 秦中 | Process for preparing high purity 1-perilla alcohol |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111217708A (en) * | 2020-02-21 | 2020-06-02 | 中国林业科学研究院林产化学工业研究所 | Preparation method and weeding application of alkyl perillamine derivative |
| CN111217708B (en) * | 2020-02-21 | 2022-07-26 | 中国林业科学研究院林产化学工业研究所 | Preparation method and weeding application of alkyl perillamine derivative |
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| Publication number | Publication date |
|---|---|
| CN109928880B (en) | 2021-08-31 |
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