CN116849216A - Application of isosteviol derivative in preventing and controlling plant diseases - Google Patents
Application of isosteviol derivative in preventing and controlling plant diseases Download PDFInfo
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- CN116849216A CN116849216A CN202310824960.9A CN202310824960A CN116849216A CN 116849216 A CN116849216 A CN 116849216A CN 202310824960 A CN202310824960 A CN 202310824960A CN 116849216 A CN116849216 A CN 116849216A
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- Prior art keywords
- isosteviol
- diseases caused
- rice
- controlling diseases
- bacteria
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- KFVUFODCZDRVSS-XGBBNYNSSA-N iso-steviol Chemical class C([C@]12C[C@@](C(C2)=O)(CC[C@H]11)C)C[C@H]2[C@@]1(C)CCC[C@@]2(C)C(O)=O KFVUFODCZDRVSS-XGBBNYNSSA-N 0.000 title claims abstract description 32
- 201000010099 disease Diseases 0.000 title claims abstract description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 19
- 241000894006 Bacteria Species 0.000 claims abstract description 9
- 241000209094 Oryza Species 0.000 claims abstract description 8
- 235000007164 Oryza sativa Nutrition 0.000 claims abstract description 8
- 235000009566 rice Nutrition 0.000 claims abstract description 8
- 241000207199 Citrus Species 0.000 claims abstract description 6
- 235000020971 citrus fruits Nutrition 0.000 claims abstract description 6
- 241000813090 Rhizoctonia solani Species 0.000 claims abstract description 5
- 241000123650 Botrytis cinerea Species 0.000 claims abstract description 4
- 241000209140 Triticum Species 0.000 claims abstract description 4
- 235000021307 Triticum Nutrition 0.000 claims abstract description 4
- 241001272684 Xanthomonas campestris pv. oryzae Species 0.000 claims abstract description 3
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical class CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 206010039509 Scab Diseases 0.000 claims description 2
- 241000221696 Sclerotinia sclerotiorum Species 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 229940102253 isopropanolamine Drugs 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 14
- 230000001580 bacterial effect Effects 0.000 abstract description 9
- 244000000005 bacterial plant pathogen Species 0.000 abstract description 4
- 241000221662 Sclerotinia Species 0.000 abstract description 3
- 150000002611 lead compounds Chemical class 0.000 abstract description 3
- 230000001954 sterilising effect Effects 0.000 abstract description 3
- 238000004659 sterilization and disinfection Methods 0.000 abstract description 3
- 235000006008 Brassica napus var napus Nutrition 0.000 abstract description 2
- 240000000385 Brassica napus var. napus Species 0.000 abstract description 2
- 241000223218 Fusarium Species 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 6
- KFVUFODCZDRVSS-UHFFFAOYSA-N isosteviol Natural products C1C(=O)C(C)(CCC23)CC21CCC1C3(C)CCCC1(C)C(O)=O KFVUFODCZDRVSS-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 239000003899 bactericide agent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 230000000843 anti-fungal effect Effects 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 244000000004 fungal plant pathogen Species 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 244000053095 fungal pathogen Species 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 238000007619 statistical method Methods 0.000 description 2
- 235000019202 steviosides Nutrition 0.000 description 2
- 241000223600 Alternaria Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 208000035240 Disease Resistance Diseases 0.000 description 1
- 241001330975 Magnaporthe oryzae Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 239000004383 Steviol glycoside Substances 0.000 description 1
- UEDUENGHJMELGK-HYDKPPNVSA-N Stevioside Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O UEDUENGHJMELGK-HYDKPPNVSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000012271 agricultural production Methods 0.000 description 1
- 238000011482 antibacterial activity assay Methods 0.000 description 1
- 238000011483 antifungal activity assay Methods 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 238000002815 broth microdilution Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 244000000003 plant pathogen Species 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229930182488 steviol glycoside Natural products 0.000 description 1
- 235000019411 steviol glycoside Nutrition 0.000 description 1
- 150000008144 steviol glycosides Chemical class 0.000 description 1
- 229940013618 stevioside Drugs 0.000 description 1
- OHHNJQXIOPOJSC-UHFFFAOYSA-N stevioside Natural products CC1(CCCC2(C)C3(C)CCC4(CC3(CCC12C)CC4=C)OC5OC(CO)C(O)C(O)C5OC6OC(CO)C(O)C(O)C6O)C(=O)OC7OC(CO)C(O)C(O)C7O OHHNJQXIOPOJSC-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229930002348 tetracyclic diterpenoid Natural products 0.000 description 1
- -1 tetracyclic diterpenoid compound Chemical class 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
Classifications
-
- 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
- A01N37/42—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 within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic 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
- 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
- A01N43/06—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 five-membered rings
- A01N43/10—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 five-membered rings with sulfur as the ring hetero atom
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
-
- 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
-
- 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
- A01P3/00—Fungicides
-
- 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
- Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
- Y02A40/10—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in agriculture
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses application of isosteviol derivatives in preventing and treating crop diseases, which can prevent and treat diseases caused by sclerotinia rot of colza, rhizoctonia solani, botrytis cinerea, gibberella wheat, rice blast, bacterial blight of rice and citrus canker. The isosteviol derivative has good antibacterial activity on most plant pathogenic bacteria, especially has strongest antibacterial activity on rice bacterial leaf blight bacteria and citrus canker bacteria, and can be further developed as a sterilization lead compound.
Description
Technical Field
The invention relates to the field of agricultural bactericides, in particular to a novel application of isosteviol derivatives as bactericides in crop disease control.
Background
Plant diseases seriously threaten the agricultural health development and the grain safety, and the grain loss caused by plant diseases per year exceeds 11% of the yield. For example, rice fields in China are affected by rice sheath blight, 600 ten thousand tons of grains are lost each year, wheat is affected by scab, and yield is reduced by 10% -30% each year. Serious occurrence of plant diseases, development of pathogen resistance, abuse of chemical bactericides and the like, aggravate the resistance of plant pathogens to bactericides and seriously threaten environmental safety and human health. Therefore, research and development of a novel pesticide with high efficiency, low toxicity and low residue, which can effectively control plant pathogenic bacteria, has become one of the primary targets of pesticide creation at present.
The isosteviol is a tetracyclic diterpenoid compound obtained by hydrolyzing natural stevioside under the action of acidity or enzyme, and has pharmacological effects of resisting tumor, reducing blood sugar, reducing blood ester, reducing blood pressure, resisting bacteria and viruses, protecting heart and nervous system, etc. In terms of plant disease resistance, only two articles report that steviol glycosides have a certain activity against agricultural fungi. However, the activity of isosteviol and its derivatives against agricultural pathogens has not been reported yet. Based on this, the present invention synthesizes a series of isosteviol derivatives IS1 to IS24, and tests the antibacterial activity against plant pathogenic fungi and plant pathogenic bacteria. The result shows that the isosteviol derivative has excellent antifungal and antibacterial activities, has good antibacterial activities on sclerotinia rot of colza, rhizoctonia solani, botrytis cinerea, gibberella wheat, rice blast and bacterial blight of rice, and citrus canker, and can be further developed as a sterilization lead compound.
Disclosure of Invention
The invention aims at overcoming the defects in the prior art, providing a natural source bactericide for agricultural production and the application of isosteviol derivatives in preventing and controlling crop diseases.
The isosteviol derivative can be used for preventing and controlling crop diseases, and can be used for preventing and controlling diseases caused by Sclerotinia sclerotiorum, rhizoctonia solani, botrytis cinerea, alternaria tricolor, pyricularia oryzae, rhizoctonia solani and Sclerotinia citri. Wherein the structural general formula of any compound containing a therapeutically effective amount is shown as the following.
Wherein R is substituted ester, substituted amide, hydrazide, substituted isopropanolamine.
Compared with the prior art, the invention has the following effects: most isosteviol derivatives have excellent antifungal and antibacterial activities, particularly have the strongest antibacterial activities on rice bacterial blight bacteria and citrus canker bacteria, and can be further developed as sterilization lead compounds.
Detailed Description
The following is a specific embodiment of the present invention, and further describes the technical solution of the present invention, but the content of the present invention is not limited to the scope of the embodiment, and all changes or equivalent substitutions without departing from the concept of the present invention are included in the scope of the present invention.
Example 1: preparation of isosteviol derivatives
Compounds IS1 to IS24 (see, for example, documents Journal ofAgricultural andFood Chemistry,2019,67,13212-13220).
The isosteviol derivatives IS1 to IS24 listed in the claims are determined by physical properties and nuclear magnetic resonance mass spectrometry, which are obtained by referring to the synthesis methods reported in the prior literature. All the compounds are separated by routine methods such as silica gel column chromatography for many times to obtain pure products for further activity test.
TABLE 1 isosteviol derivatives
Example 2: indoor antifungal Activity assay
The hypha growth rate method is adopted: according to a certain concentration gradient, the test compound is added into a culture medium which is sterilized and cooled to about 50 ℃, the mixture is uniformly mixed, the medicament is diluted into a series of concentrations to prepare a medicament-containing culture medium, each culture dish is inoculated with a bacterial dish (diameter d=5 mm), and each concentration is set to 3 times. The colony diameters (mm) of the respective concentrations were measured by the crisscross method when the control colonies were grown to 2/3 or more in the culture dish at 25℃and the growth inhibition ratios of the mycelia by the agents were calculated, and the differential statistical analysis was performed by using statistical software SAS8.1 (Statistical Analysis System 8.1.1). The inhibitory effect of isosteviol derivatives on 5 plant pathogenic fungi was measured and the results are shown in table 2.
TABLE 2 inhibitory Activity of isosteviol derivatives against pathogenic fungi
As can be seen from the results of the biological tests in Table 2, the isosteviol derivative disclosed by the invention has good bactericidal activity on most pathogenic fungi, and is obviously superior to isosteviol. In particular isopropanolamines IS11, IS14, IS16, IS18, IS19 and IS21 have excellent antifungal activity against 5 plant pathogenic fungi, and the inhibition rate of the isopropanolamine compounds on 5 fungi IS more than 50% at the concentration of 50 mug/mL.
Example 3: indoor antibacterial Activity assay
The trace broth dilution method is adopted: agricultural bacteria were inoculated into 20mL of NB medium and then incubated in a thermostated shaker at 37 ℃ for 12h at 150rpm. Measuring absorbance at 600nm with enzyme-labeled instrument, and taking culture solution without bacteria as blank control according to OD 600 0.1 corresponds to a concentration of 1X 10 8 cfu/mL, diluting the bacterial suspension with NB medium to a concentration of 1X 10 6 After cfu/mL of bacterial liquid, the bacterial liquid is reserved for standby. Sucking 50. Mu.L of diluted bacterial liquid by a discharge gun, placing the bacterial liquid in a 96-well plate, and sequentially adding 50. Mu.L of compound solutionThe blank control was PBS solution added at equal volumes, the positive control was copper thiabendazole, and 3 replicates were set for each concentration. After the sample was incubated in a constant temperature incubator at 37℃for 24 hours, the OD value at 600nm was measured, and the inhibition ratio was calculated. The inhibitory effect of isosteviol derivatives on 2 plant pathogenic bacteria was measured and the results are shown in table 3.
TABLE 3 inhibitory Activity of isosteviol derivatives against phytopathogenic bacteria
As can be seen from the results of the biological tests in Table 3, the isosteviol derivatives according to the present invention exhibit good bactericidal activity against most pathogenic bacteria, which is significantly superior to isosteviol. In particular, the compounds IS13, IS14, IS15 and IS18 have the strongest activity on rice bacterial leaf blight and citrus canker, and have MIC values of 6.25 mug/mL.
Claims (8)
1. New use of isosteviol derivative in crop disease control is provided. The isosteviol derivatives IS1 to IS24 have the following molecular structures.
Wherein R is substituted ester, substituted amide, hydrazide, substituted isopropanolamine.
2. Use of isosteviol derivatives according to claim 1 for controlling diseases caused by sclerotinia sclerotiorum.
3. Use of an isosteviol derivative according to claim 1 for controlling diseases caused by rhizoctonia solani.
4. Use of the isosteviol derivative according to claim 1 for controlling diseases caused by botrytis cinerea.
5. Use of the isosteviol derivative according to claim 1 for controlling diseases caused by wheat scab.
6. Use of isosteviol derivatives according to claim 1 for controlling diseases caused by rice blast bacteria.
7. Use of the isosteviol derivative according to claim 1 for controlling diseases caused by bacterial blight of rice.
8. Use of the isosteviol derivative according to claim 1 for controlling diseases caused by citrus canker.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310824960.9A CN116849216A (en) | 2023-07-06 | 2023-07-06 | Application of isosteviol derivative in preventing and controlling plant diseases |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310824960.9A CN116849216A (en) | 2023-07-06 | 2023-07-06 | Application of isosteviol derivative in preventing and controlling plant diseases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116849216A true CN116849216A (en) | 2023-10-10 |
Family
ID=88218540
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310824960.9A Pending CN116849216A (en) | 2023-07-06 | 2023-07-06 | Application of isosteviol derivative in preventing and controlling plant diseases |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116849216A (en) |
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2023
- 2023-07-06 CN CN202310824960.9A patent/CN116849216A/en active Pending
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