CN116158437A - Application of coumarin-3-carboxylic acid in preventing and treating plant bacterial diseases - Google Patents
Application of coumarin-3-carboxylic acid in preventing and treating plant bacterial diseases Download PDFInfo
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- CN116158437A CN116158437A CN202310052487.7A CN202310052487A CN116158437A CN 116158437 A CN116158437 A CN 116158437A CN 202310052487 A CN202310052487 A CN 202310052487A CN 116158437 A CN116158437 A CN 116158437A
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- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
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- Agronomy & Crop Science (AREA)
- Health & Medical Sciences (AREA)
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Abstract
The coumarin-3-carboxylic acid provided by the invention has obvious inhibition effect on plant bacterial diseases, wherein the plant bacterial diseases are rice bacterial leaf blight bacteria, rice bacterial leaf spot bacteria, citrus canker bacteria, melon bacterial fruit spot bacteria, tomato bacterial wilt bacteria, strawberry bacterial angular leaf spot bacteria, cabbage black rot bacteria, cabbage soft rot bacteria, potato soft rot bacteria, mango bacterial angular leaf spot bacteria, cassava bacterial wilt bacteria, cucumber bacterial angular leaf spot bacteria, kiwi fruit canker bacteria and banana bacterial soft rot bacteria, and the coumarin-3-carboxylic acid has protection and treatment effects on melon bacterial fruit spot diseases.
Description
Technical Field
The invention relates to the field of plant bacterial disease control, in particular to application of coumarin-3-carboxylic acid in control of plant bacterial diseases.
Background
Coumarin-3-carboxylic acid (also called benzopyranone formic acid), 2-oxo-2H-1-benzopyran-3-carboxylic acid, belongs to coumarin compounds, and has chemical structure shown in figure 1. The molecular formula is C10H6O4, the relative molecular weight is 190.15, and the coumarin derivatives have various biological activities such as anti-tumor, lactic acid transport inhibition, GPR35 agonism and the like. In recent years, with the continuous intensive research on the structure of the compound, the strong GPR35 agonist (6-bromo-8-nitro-7-hydroxy-3-tetrazole coumarin) with good patent application prospect can be obtained after modification and reconstruction of groups with different properties at different positions of the compound, and has good patent application prospect and development value (Wei L, wang JX, zhang XL, wang P, zhao YP, li JQ, hou T, qu LL, shi LY, liang XM, fang Y.discover of 2H-color-2-one derivatives as GProtein-Coupled Receptor-35agonists.Journal of Medicinal Chemistry,2017,60:362-372.). And can show excellent inhibitory activity on various medical bacteria after pyrazole amide drug effect fragments are introduced into carboxylic acid positions of the bacteria (Liu H, ren ZL, gong JX, chu MJ, ma QW, wang JC, lv XH.Novel coumarin-pyrazole carboxamide derivatives as potential topoisomerase II inhibitors: design, synchronization, and antibacterial activity.European Journal of Medicinal Chemistry,2018, 157:81-87).
Through searching, no report on agricultural activity of coumarin-3-carboxylic acid is found at home and abroad, and no report on inhibition effect of coumarin-3-carboxylic acid on plant pathogenic bacteria is found.
Disclosure of Invention
In view of the above, the present invention proposes the application of coumarin-3-carboxylic acid in preventing and treating plant bacterial diseases, and solves the above problems.
The technical scheme of the invention is realized as follows:
the application of coumarin-3-carboxylic acid in preventing and treating plant bacterial diseases.
Further, the active ingredient is coumarin-3-carboxylic acid, and an auxiliary agent is optionally added.
Further, the coumarin-3-carboxylic acid concentration is 150-550mg/L.
Furthermore, the coumarin-3-carboxylic acid can be prepared into suspending agents, aqueous emulsion, microemulsion, emulsifiable concentrates, wettable powder, water dispersible granules or ultra-low volume liquid.
Further, the plant bacterial diseases are bacterial leaf blight bacteria, bacterial leaf spot bacteria, citrus canker bacteria, bacterial fruit spot bacteria of melon, bacterial wilt bacteria of tomato, bacterial angular leaf spot bacteria of strawberry, black rot bacteria of cabbage, soft rot bacteria of potato, bacterial angular leaf spot bacteria of mango, bacterial wilt bacteria of cassava, bacterial angular leaf spot bacteria of cucumber, bacterial canker bacteria of kiwi and bacterial soft rot bacteria of banana.
Furthermore, the coumarin-3-carboxylic acid has an antibacterial effect on plant bacterial diseases.
Furthermore, the coumarin-3-carboxylic acid with the concentration of 50-250mg/L has the protection and treatment effects on melon bacterial fruit blotch.
Further, coumarin-3-carboxylic acids can be synthesized chemically. The compound is white powder, CAS number is 531-81-7, molecular formula is C10H6O4, and molecular weight is 190.15.
Compared with the prior art, the invention has the beneficial effects that:
when the tested concentration of the coumarin-3-carboxylic acid is 500mg/L, the coumarin-3-carboxylic acid has good antibacterial effect on rice bacterial blight bacteria, melon bacterial fruit blotch bacteria, citrus canker bacteria, tomato bacterial wilt bacteria and mango bacterial black spot bacteria, the inhibition rate is over 90 percent, and the inhibition rate is 77.16 percent.
When the tested concentration is 100 mug/mL, the coumarin-3-carboxylic acid has excellent antibacterial effect on mango bacterial angular leaf spot bacteria, rice bacterial leaf blight bacteria, melon bacterial fruit spot bacteria, tomato bacterial wilt bacteria and banana soft rot bacteria, and the inhibition rates are 88.45%, 84.39%, 90.45%, 83.76 and 82.38% respectively; the plant extract also has certain antibacterial effect on strawberry bacterial angular leaf spot bacteria and cucumber bacterial angular leaf spot bacteria, and the inhibition rates are respectively 70.55% and 73.02%.
The potting test result shows that the coumarin-3-carboxylic acid has a strong protection effect on melon bacterial fruit blotch, and the protection effect is 61.88% when the tested concentration is 200mg/L, which is obviously better than that of the control medicament thiabendazole; the bactericidal composition also has a stronger treatment effect on melon bacterial fruit blotch, and the treatment effect is 53.19% when the tested concentration is 200mg/L, which is obviously superior to that of a control medicament thiabendazole.
In a word, the compound provided by the invention has remarkable inhibition effect on plant pathogenic bacteria, and provides a natural source bactericidal active substance for agricultural disease control; the compound can be used for preventing and treating various important agricultural diseases such as bacterial leaf blight of rice, bacterial black spot of mango, bacterial fruit spot of melon and the like; the bactericide is used as a bactericide, and the characteristics of high efficiency, low toxicity, safety and the like meet the requirements of the current new pesticide preparation.
Detailed Description
In order to better understand the technical content of the present invention, the following provides specific examples to further illustrate the present invention.
1. Application of coumarin-3-carboxylic acid in preventing and treating plant diseases
The inventor finds that coumarin-3-carboxylic acid has excellent antibacterial effect on plant pathogenic bacteria in agricultural bactericidal screening of coumarin compounds. The following experiments are taken as examples to verify the effect of coumarin-3-carboxylic acid in controlling plant bacterial diseases.
1. Sources of coumarin-3-carboxylic acids
Coumarin-3-carboxylic acid, coumarin-3-carboxilic acid, CAS number 531-81-7, purity greater than 97%, purchased from Shanghai Bi De medical science and technology Co.
2. Determination of the inhibitory Activity of coumarin-3-carboxylic acids against phytopathogenic bacteria
1. Test strain
Mango bacterial angular leaf spot Xanthomonas campestris pv.mangiferindate, citrus canker x.axonosporis pv.citri, rice bacterial leaf blight x.oryzae pv.oryzae, rice bacterial strip leaf spot x.oryzae pv.oryzicola, strawberry bacterial angular leaf spot x.fragariae, black rot of cabbage x.campestris pv.campestris, cassava bacterial wilt x.axonosporis pv.mangifetis, cucumber bacterial angular leaf spot Pseudomonas syringae pv.lachrymans, kiwi fruit canker p.coringae pv.actinidae, melon bacterial fruit spot Acidovorax citrulli, tomato bacterial wilt Ralstonia solanacearum, potato soft rot Pectobacterium carotovorum subsp.sapiense, cabbage soft rot p.carotovorous, banana soft rot.
2. Test method
2.1 in vitro Activity assay
The invention adopts 96-well plate method to evaluate the antibacterial activity of the compound to plant pathogenic bacteria. The inhibitory activity of coumarin-3-carboxylic acid against the above plant pathogenic bacteria was measured by 96-well plate method using the method of using Shichao (Dan Chaodeng. Protocatechuic aldehyde to inhibit Cronobacter sakazakii and mechanism [ J ]. Modern food technology, 2017,33 (07): 105-111, 62.) and the prepared bacterial suspension was added to 96-well ELISA plate at 10. Mu.L per well. The sample control was added with 10 μl of bacterial suspension and 200 μl of liquid medium, the blank control was added with 200 μl of liquid medium, and the compound solution control was set up with 200 μl per well. Blowing and uniformly mixing the medicament solution and the bacterial suspension, placing the sample in an incubator for vibration (500 r/min) culture, setting the culture temperature to be 28-30 ℃ and the culture time to be 18-24 h, and measuring the absorbance of the bacterial solution by using an enzyme-labeled instrument. The inhibitory effect of the compound on pathogens was calculated using the following formula.
Antibacterial ratio (%) = { (control OD) 600 Blank OD 600 ) - (test group OD 600-Compound solution control OD 600) }/(control group OD 600-blank control group OD 600) X100%
2.2 data analysis
The antibacterial activity of coumarin-3-carboxylic acid against 14 plant pathogenic bacteria was tested indoors and the results are shown in table 1. When the tested concentration is 100 mug/mL, the coumarin-3-carboxylic acid has excellent antibacterial effect on mango bacterial angular leaf spot bacteria, rice bacterial leaf blight bacteria, melon bacterial fruit spot bacteria, tomato bacterial wilt bacteria and banana soft rot bacteria, and the inhibition rates are 88.45%, 84.39%, 90.45%, 83.76 and 82.38% respectively; the plant extract also has certain antibacterial effect on strawberry bacterial angular leaf spot bacteria and cucumber bacterial angular leaf spot bacteria, and the inhibition rates are respectively 70.55% and 73.02%; the antibacterial activity to white vegetable soft rot fungi is poor, and the inhibition rate is only 30.23%.
TABLE 1 bacteriostatic Activity of coumarin-3-carboxylic acids against 8 plant pathogenic bacteria
2.2 potted plant test method
The coumarin-3-carboxylic acid slightly improves the in vivo pot test reference method for bacterial fruit blotch of melon: uniformly spraying 100mg/L of thiabendazole copper suspension with concentration of 1, concentration of 2, concentration of 3 and concentration of 20% and 5 treatments of clear water on melon (variety: nectar) seedlings, and then spraying and inoculating fruit spot germ suspension (concentration is 1×10) in each pot 9 CFU/mL), each treatment was repeated 3 times, each 6 seedlings were repeated, each 1 plant was cultivated by moisturizing light, the disease condition was observed at 7d and 14d of cultivation, and the disease index (formula 1) and the control effect (formula 2) were calculated [ reference: identification of bacillus BJ_6 and prevention and treatment of bacterial fruit blotch of melon (melons) _ Gu Huihui]. Leaf disease grade grading [ reference "second drug efficacy" Bactericide for preventing and controlling cucumber bacterial angular leaf spot pathogen ] "]：
Level 0: no disease spots;
stage 1: the area of the disease spots accounts for less than 5% of the whole leaf area;
3 stages: the area of the lesion accounts for 6-10% of the whole leaf area;
5 stages: the area of the lesion accounts for 11-20% of the whole leaf area;
7 stages: the area of the lesion accounts for 21-50% of the whole leaf area;
stage 9: the area of the disease spots accounts for more than 51% of the whole leaf area;
the drug effect calculation formula:
disease index = Σ (leaf number of each stage×relative stage value)/(total leaf number of investigation×highest stage value) ×100 (1)
Control effect (%) = (control disease index-treatment disease index)/control disease index×100 (2)
The potted plant test results show (Table 2) that coumarin-3-carboxylic acid has stronger protection and treatment effects on melon bacterial fruit blotch, wherein the protection effect is better than the treatment effect. When the tested concentration is 200mg/L, the protective effect can reach 61.88%, which is obviously superior to that of the control medicament thiabendazole; the bactericidal composition also has a stronger treatment effect on melon bacterial fruit blotch, and the treatment effect is 53.19% when the tested concentration is 200mg/L, which is obviously superior to that of a control medicament thiabendazole.
TABLE 2 protection and treatment of bacterial fruit blotches of melon by coumarin-3-carboxylic acids
The foregoing description of the preferred embodiments of the invention is not intended to be limiting, but rather is intended to cover all modifications, equivalents, alternatives, and improvements that fall within the spirit and scope of the invention.
Claims (8)
1. The application of coumarin-3-carboxylic acid in preventing and treating plant bacterial diseases.
2. The use according to claim 1, wherein the coumarin-3-carboxylic acid is an active ingredient.
3. The use according to claim 1, wherein the coumarin-3-carboxylic acid concentration is 50-550mg/L.
4. The use according to claim 1, wherein the coumarin-3-carboxylic acid is formulated as a suspension, emulsion in water, microemulsion, emulsifiable concentrate, wettable powder, water dispersible granule or ultra low volume liquid.
5. The use according to claim 1, wherein the plant bacterial disease is bacterial leaf blight of rice, bacterial leaf spot of rice, citrus canker, bacterial fruit spot of melon, bacterial wilt of tomato, bacterial angular leaf spot of strawberry, black rot of cabbage, soft rot of potato, bacterial angular leaf spot of mango, bacterial wilt of cassava, bacterial angular leaf spot of cucumber, bacterial canker of kiwi and bacterial soft rot of banana.
6. The use according to claim 5, wherein the coumarin-3-carboxylic acid has an antibacterial effect against plant bacterial diseases.
7. The use according to claim 1, wherein the coumarin-3-carboxylic acid has a protective and therapeutic effect on bacterial fruit blotch of melon.
8. The use according to claim 7, wherein the coumarin-3-carboxylic acid concentration is 50-250mg/L.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310052487.7A CN116158437A (en) | 2023-02-02 | 2023-02-02 | Application of coumarin-3-carboxylic acid in preventing and treating plant bacterial diseases |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202310052487.7A CN116158437A (en) | 2023-02-02 | 2023-02-02 | Application of coumarin-3-carboxylic acid in preventing and treating plant bacterial diseases |
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- 2023-02-02 CN CN202310052487.7A patent/CN116158437A/en active Pending
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