CN114027300B - Application of isoeugenol and methylation derivative metabolite thereof in inhibiting phytophthora infestans and preventing and treating plant diseases - Google Patents
Application of isoeugenol and methylation derivative metabolite thereof in inhibiting phytophthora infestans and preventing and treating plant diseases Download PDFInfo
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- CN114027300B CN114027300B CN202111284626.6A CN202111284626A CN114027300B CN 114027300 B CN114027300 B CN 114027300B CN 202111284626 A CN202111284626 A CN 202111284626A CN 114027300 B CN114027300 B CN 114027300B
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- BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Natural products COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 title claims abstract description 126
- 241000233622 Phytophthora infestans Species 0.000 title claims abstract description 70
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 title claims abstract description 65
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- 230000002401 inhibitory effect Effects 0.000 title claims abstract description 13
- BJIOGJUNALELMI-ARJAWSKDSA-N cis-isoeugenol Chemical compound COC1=CC(\C=C/C)=CC=C1O BJIOGJUNALELMI-ARJAWSKDSA-N 0.000 title claims abstract 11
- 230000011987 methylation Effects 0.000 title abstract description 33
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- 238000000034 method Methods 0.000 claims abstract description 10
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- NNWHUJCUHAELCL-UHFFFAOYSA-N cis-Methyl isoeugenol Natural products COC1=CC=C(C=CC)C=C1OC NNWHUJCUHAELCL-UHFFFAOYSA-N 0.000 claims description 30
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Classifications
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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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
- A01G13/00—Protecting plants
-
- 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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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention belongs to the technical field of biological pesticides, and in particular relates to application of isoeugenol and methylation derivative metabolites thereof in inhibiting phytophthora infestans and preventing and treating plant diseases. The isoeugenol and the methylation derivative metabolite thereof have high-efficiency inhibition effect on phytophthora infestans, and the inhibition effect is obviously higher than that of eugenol under the condition of the same addition concentration. The isoeugenol and the methylation derivative metabolite thereof can be used as biological pesticides for preventing and treating potato late blight and/or tomato late blight, and have the advantages of safety, environmental protection, simple application method, low cost and easy popularization and application.
Description
Technical Field
The invention belongs to the technical field of biological pesticides, and in particular relates to application of isoeugenol and methylation derivative metabolites thereof in inhibiting phytophthora infestans and preventing and treating plant diseases.
Background
Tomato and potato late blight caused by phytophthora infestans (Phytophthora infestans de Bary) is one of the most serious crop diseases in China and even worldwide, and causes a loss of dollar value of 30 to 100 million to the global potato industry each year. The current mainstream phytophthora infestans prevention and control means highly depend on chemical synthetic pesticides such as fluazinam, mancozeb and the like, but environmental toxicity and potential physiological toxicity to human bodies caused by long-term high-frequency chemical pesticide spraying are increasingly prominent. For example, fluazinam has acute toxicity to aquatic organisms such as zebra fish and African frog, and can be enriched in zebra fish; mancozeb contributes to worsening of the degree of nonalcoholic fatty liver in experiments on cell lines outside the human body, and its degradation metabolites may cause various health risks. For the above reasons, the european union has no longer approved the use of pesticides containing mancozeb since day 1 and 4 of 2021. Therefore, development of a novel green pesticide having a good control effect on phytophthora infestans and being environmentally friendly is needed.
Plants are rich in natural products, which often have important functions for the plant's own biotic stress resistance. Therefore, plant natural products that can inhibit the growth of phytophthora infestans have the potential to be developed as green biopesticides against this important pathogen. The traditional biological pesticide excavating technical scheme is established on a biological substance separation and purification method taking biological activity as a guide. Based on this method, natural products derived from plants including eugenol (CAS 97-53-0), matrine (CAS 519-02-8), carvacrol (CAS 499-75-2) and the like are currently marketed and used as biopesticides for controlling phytophthora infestans. Wherein eugenol (0.3% solution) shows a prevention and control effect which is not inferior to that of the traditional chemical pesticide in repeated field experiments, and has no obvious negative effects on tomato plants, potato plants and potato blocks. Eugenol is a plant-derived green biopesticide with the best prevention and control effect on phytophthora infestans at present, but whether plant natural products with stronger inhibition effect on the phytophthora infestans exist in nature still needs to be further explored and verified.
Like eugenol, isoeugenol and methyl isoeugenol are food flavoring agents which are double-certified by the Joint Expert Committee for Food Additives (JECFA) of the european union Food Improvement Agents and the joint grain and agricultural organization-the world health organization, and have no toxic effect on human bodies at conventional dosages. Eugenol, isoeugenol and methylisoeugenol also showed similar LD in the mouse injection and rat oral experiments 50 The dose, the safety of these three substances was seen to be comparable. Specifically, eugenol, isoeugenol and methyl isoeugenol are used as mice injection toxicity LD 50 The dosage is 500mg/kg, 328mg/kg and 570mg/kg respectively, and the oral toxicity LD of rats 50 The dosages are 1930mg/kg, 1560mg/kg and 2500mg/kg respectively. However, research and application of isoeugenol and methyl isoeugenol in inhibiting phytophthora infestans and preventing and controlling plant diseases have not been reported yet.
Disclosure of Invention
Aiming at the problems of large harm of chemical pesticides, few plant source green biopesticide resources and the like in the prior art, the invention aims to provide the application of isoeugenol and methylation derivative metabolites thereof in the inhibition of phytophthora infestans and the control of plant diseases, is safe and environment-friendly, has good inhibition effect on the phytophthora infestans, and can be widely applied to the control of potato late blight and/or tomato late blight.
To achieve the above object, the present invention provides in a first aspect the use of isoeugenol and its methylation derived metabolites in the inhibition of phytophthora infestans.
As a further embodiment of the present invention, the isoeugenol has a half-inhibitory concentration IC against Phytophthora infestans 50 65.5mg/L.
As a further embodiment of the invention, the methylation-derived metabolite of isoeugenol has a half inhibitory concentration IC against Phytophthora infestans 50 57.9mg/L.
As a further embodiment of the invention, the use includes controlling plant diseases.
As a further embodiment of the present invention, the plant disease includes potato late blight and/or tomato late blight, and the pathogenic bacteria of the plant disease is phytophthora infestans.
As a further embodiment of the invention, the use comprises the preparation of a pesticide.
As a further embodiment of the present invention, the pesticide-inhibited pathogenic bacteria include phytophthora infestans.
As a further embodiment of the present invention, the pesticide is a formulation made from the isoeugenol and a suitable adjuvant, or the pesticide is a formulation made from a methylation-derived metabolite of the isoeugenol and a suitable adjuvant;
the preparation is a soluble agent, a water dispersible granule, an aqueous emulsion or wettable powder;
preferably, the pesticide is a soluble agent; in the soluble agent, the weight percentage of isoeugenol or isoeugenol methylation derivative metabolite is 0.3%, and the application dosage of the pesticide is 90-120 ml/mu;
preferably, the pesticide is an aqueous emulsion; in the aqueous emulsion, the weight percentage of isoeugenol or the metabolic product derived from the methylation of isoeugenol is 20%, and the application dosage of the pesticide is 30-45 ml/mu.
As a further embodiment of the present invention, the adjuvant comprises a pesticide carrier and a pesticide adjuvant;
the pesticide carrier is a liquid carrier or a solid carrier, the liquid carrier is deionized water, distilled water or tap water, and the solid carrier is one or more selected from kaolin, bentonite, diatomite, calcium carbonate, white carbon black and attapulgite;
the pesticide auxiliary agent is one or more selected from emulsifying agent, dispersing agent, wetting agent, thickening agent, defoaming agent, oxidant, antifreezing agent, disintegrating agent and filler.
In a second aspect, the present invention provides a method of controlling plant diseases using isoeugenol and its methylation derived metabolites by applying said isoeugenol or said methylation derived metabolites of isoeugenol to the stem, leaf, root or seed of a plant in a bacterially effective amount by spraying, root application or seed coating; the plant diseases are potato late blight and/or tomato late blight, and pathogenic bacteria of the plant diseases are phytophthora infestans.
Compared with the prior art, the invention has the following beneficial effects:
(1) The isoeugenol and the methylation derivative metabolite thereof have high-efficiency inhibition effect on phytophthora infestans, and the inhibition effect is obviously higher than that of eugenol under the condition of the same addition concentration;
(2) The isoeugenol and the methylation derivative metabolite thereof belong to plant sources, and are free of pollution to the environment and health hazard to human bodies when used for preventing and treating potato late blight and/or tomato late blight;
(3) When the isoeugenol and the methylation derivative metabolite thereof are used as pesticides, the isoeugenol and the methylation derivative metabolite thereof can be used in the sowing period, the growing period and the harvesting period of plants, and have the advantages of simple application method, low cost and easiness in popularization and application.
Drawings
FIG. 1 shows inhibition of plate growth of Phytophthora infestans by eugenol, isoeugenol and methyl isoeugenol at various additive concentrations;
FIG. 2 is a graph comparing hyphal diameters of Phytophthora infestans when eugenol, isoeugenol and methyl isoeugenol are added at different concentrations;
FIG. 3 is a graph comparing the growth inhibition rates of eugenol, isoeugenol and methyl isoeugenol against Phytophthora infestans at different additive concentrations, wherein the inhibition rates of the different test substances at the same concentration are represented by different letters a, b or c; p <0.05; the data in the figure are obtained by analyzing experimental results by single-factor analysis of variance (One-way ANOVA).
Detailed Description
In order to describe the technical content, constructional features, achieved objects and effects of the technical solution in detail, the following description is made in connection with the specific embodiments in conjunction with the accompanying drawings. The present embodiment is implemented on the premise of the technical scheme of the present invention, and a detailed implementation manner and a specific operation process are provided, but the protection scope of the present invention is not limited to the following embodiments.
The test materials, reagents and the like used in the examples described below are commercially available unless otherwise specified. The experimental methods in the following examples are conventional methods unless otherwise specified.
In the examples of the present invention, the plant-derived green biopesticide used was eugenol (CAS 97-53-0), available from Beijing Walker Biotechnology Co., ltd. (cat# V900001; purity: 98%); isoeugenol (CAS 97-54-1), an isomer of eugenol, available from Beijing Qianlida Biotech Co., ltd. (cat# S5757; purity: 98%; cis-trans isomer mixture); and methyl isoeugenol (CAS 93-16-3), a methylation-derived metabolite of isoeugenol, available from Vickers biotechnology Co., ltd. In Sichuan province (cat number wkq-02032; purity 98%; cis isomer).
In an embodiment of the invention, the Phytophthora infestans strain used is T30-4. In an embodiment of the invention, the configuration method of the rye culture medium used is as follows: 60 g of rye kernel is added with a proper amount of pure water, soaked for 12-24 hours at 4 ℃, crushed for 1 minute by a wall breaking machine in the next day, filtered to remove residues, added with 20 g of sucrose and 13.5 g of agar powder, fixed to 1 liter, sterilized at 121 ℃ under high pressure for 20 minutes, poured into a culture dish and cooled to room temperature.
First, the use of isoeugenol and its methylation-derived metabolites in the inhibition of Phytophthora infestans according to the first aspect of the present invention is described. The methylation derivative metabolite of isoeugenol is methyl isoeugenol.
In the embodiment of the invention, the median inhibitory concentration IC of isoeugenol to phytophthora infestans 50 65.5mg/L.
In the embodiment of the invention, the methylation derivative metabolite of isoeugenol has half inhibition concentration IC to phytophthora infestans 50 57.9mg/L.
The isoeugenol and its methylation derivative metabolite (methyl isoeugenol) have remarkable inhibition effect on phytophthora infestans growth, and under the condition of the same addition concentration, the inhibition rate of the isoeugenol and its methylation derivative metabolite is remarkably higher than that of eugenol, and the two substances can be used as active ingredients or pesticides for inhibiting phytophthora infestans and preventing and treating plant diseases caused by the phytophthora infestans.
Thus, in some embodiments of the invention, the application includes controlling plant diseases.
In some embodiments of the invention, the plant disease comprises potato late blight and/or tomato late blight, and the pathogenic bacteria of the plant disease is phytophthora infestans.
In some embodiments of the invention, the application comprises preparing a pesticide.
In some embodiments of the invention, the pesticide-inhibited pathogenic bacteria include phytophthora infestans.
In some embodiments of the invention, the pesticide is a formulation made from the isoeugenol and a suitable adjuvant, or the pesticide is a formulation made from a methylation-derived metabolite of the isoeugenol and a suitable adjuvant;
the preparation is a soluble agent, a water dispersible granule, an aqueous emulsion or a wettable powder.
Of course, in other embodiments, the formulation may be other pesticidally acceptable dosage forms including, but not limited to, emulsifiable concentrates, microemulsions, seed coatings, dry suspensions, and the like, as the case may be.
Preferably, the pesticide is a soluble agent; in the soluble agent, the weight percentage of isoeugenol or isoeugenol methylation derivative metabolite is 0.3%, and the application dosage of the pesticide is 90-120 ml/mu;
preferably, the pesticide is an aqueous emulsion; in the aqueous emulsion, the weight percentage of isoeugenol or the metabolic product derived from the methylation of isoeugenol is 20%, and the application dosage of the pesticide is 30-45 ml/mu.
When the isoeugenol and the methylation derivative metabolite thereof are used as pesticides for preventing and treating plant diseases (potato late blight and/or tomato late blight), the isoeugenol and the methylation derivative metabolite thereof can be directly used as active ingredients, and pesticide preparations can be prepared by adding carriers, auxiliary agents and the like which are acceptable in pesticides.
Thus, in some embodiments of the invention, the adjuvant comprises a pesticide carrier and a pesticide adjuvant;
the pesticide carrier is a liquid carrier or a solid carrier, the liquid carrier is deionized water, distilled water or tap water, and the solid carrier is one or more selected from kaolin, bentonite, diatomite, calcium carbonate, white carbon black and attapulgite;
the pesticide auxiliary agent is one or more selected from emulsifying agent, dispersing agent, wetting agent, thickening agent, defoaming agent, oxidant, antifreezing agent, disintegrating agent and filler.
In some embodiments of the present invention, the above auxiliary materials (pesticide carrier and pesticide adjuvant) may be suitably used according to a usual method, and specific components and amounts may be determined by experiments as needed, and are not particularly limited herein.
The above-mentioned pesticide preparation can be prepared by conventional processing method, i.e. after mixing the active ingredient (isoeugenol or methyl isoeugenol) with liquid carrier or solid carrier, adding one or more of above-mentioned pesticide adjuvants such as emulsifying agent, dispersing agent, etc. In each case, a uniform distribution of the active ingredient in the above-mentioned pesticide formulation should be ensured.
Of course, in some embodiments of the invention, isoeugenol or methyl isoeugenol can also be mixed with other agriculturally active ingredients to make the desired dosage form for use in inhibiting phytophthora infestans and controlling plant diseases.
In a second aspect, the present invention provides a method of controlling plant diseases using isoeugenol and its methylation derived metabolites by applying said isoeugenol or said methylation derived metabolites of isoeugenol to the stem, leaf, root or seed of a plant in a bacterially effective amount by spraying, root application or seed coating; the plant diseases are potato late blight and/or tomato late blight, and pathogenic bacteria of the plant diseases are phytophthora infestans.
EXAMPLE 1 test of the inhibition effect of isoeugenol and methyl isoeugenol on Phytophthora infestans
Test substances (isoeugenol and methyl isoeugenol) with different concentrations are added into a rye culture medium, isoeugenol with equal concentrations and a culture medium without the addition are used as a control, and the growth inhibition effect of isoeugenol and methyl isoeugenol on phytophthora infestans is tested through a growth rate experiment after phytophthora infestans cake inoculation.
Specifically, the growth diameter of hyphae radiation on each medium was measured after 7 days (18℃dark culture) of the bacterial cake inoculation culture. The difference in hypha radiation growth diameter at the concentration tested was compared with that in the blank by Dunnett test for each test substance.
The growth inhibition rate of phytophthora infestans is calculated according to the following formula:
growth inhibition = (average diameter of blank control group-each biological repetition diameter of test group)/average diameter of blank control group
Comparison of inhibition efficiency between each test substance was performed by one-way variance detection at the same concentration as Tukey HSD detection (10 biological replicates per test substance per detection concentration). Substances that have consistent significant differences in concentration across multiple concentrations are thus detected as having significant differences in the inhibition efficiency against phytophthora infestans. At the same time, by leveling each test substance at each detected concentrationThe IC of each test substance can be calculated by carrying out logistic regression analysis on the average growth inhibition rate 50 Values. The test results are shown in Table 1. As can be seen from Table 1, the median inhibitory concentration IC of isoeugenol against Phytophthora infestans 50 Half inhibition concentration IC of methyl isoeugenol to phytophthora infestans at 65.5mg/L 50 At 57.9mg/L, significantly lower than eugenol (IC) 50 ：152.2mg/L)。
As shown in fig. 1 and 2, the radiation growth diameter of phytophthora infestans was significantly reduced at 40mg/L eugenol, isoeugenol and methyl isoeugenol addition, and further reduced with increasing concentrations of each test substance, compared to no-addition medium control, at equal concentration addition.
The inhibition rates of the respective substances on phytophthora infestans under the condition of equal concentration were further compared, and the results are shown in fig. 3. As can be seen from fig. 3, isoeugenol and methyl isoeugenol have stronger phytophthora infestans inhibition rates than eugenol at each of the tested concentrations; meanwhile, under lower concentration (40 mg/L and 60 mg/L), the inhibition rate of phytophthora infestans of methyl isoeugenol is obviously higher than that of isoeugenol; and the phytophthora infestans inhibition rate of isoeugenol is obviously higher than that of methyl isoeugenol at the concentration of 120 mg/L.
TABLE 1 inhibition efficiency of eugenol, isoeugenol and methyl isoeugenol on Phytophthora infestans
The test results show that isoeugenol and methylation derivative metabolite (methyl isoeugenol) thereof have remarkable inhibition effect on phytophthora infestans growth, and under the condition of the same addition concentration, the inhibition rate of the isoeugenol is remarkably higher than that of eugenol, so that the two substances have development and application values as pesticides for controlling potato late blight/tomato late blight caused by phytophthora infestans and the like.
With reference to the dosage of eugenol pesticide applied on the market, isoeugenol and its methylation derivative metabolite (methyl isoeugenol) can be prepared into soluble agent with the effective component content of 0.3% (weight), and can be applied at 90-120 ml/mu, or can be prepared into aqueous emulsion with the effective component content of 20% (weight), and can be applied at 30-45 ml/mu.
It should be noted that, although the foregoing embodiments have been described herein, the scope of the invention is not limited thereto, and technical parameters that are not described in detail may still be the same as or similar to the above embodiments when they are changed within the scope of the invention, and still fall within the scope of the invention. Therefore, based on the innovative concepts of the present invention, alterations and modifications to the embodiments described herein, or equivalent structures or equivalent flow transformations made by the present description and drawings, apply the above technical solution, directly or indirectly, to other relevant technical fields, all of which are included in the scope of the invention.
Claims (12)
1. The application of isoeugenol and methyl isoeugenol in inhibiting phytophthora infestans.
2. The use according to claim 1, wherein the isoeugenol has a half maximal inhibitory concentration IC against phytophthora infestans 50 65.5mg/L.
3. The use according to claim 1, wherein the methyl isoeugenol has a half inhibitory concentration IC against phytophthora infestans 50 57.9mg/L.
4. The use according to claim 1, wherein the use comprises controlling plant diseases.
5. The use according to claim 4, wherein the plant disease comprises potato late blight and/or tomato late blight and the pathogenic bacteria of the plant disease is phytophthora infestans.
6. The use according to claim 1, characterized in that the use comprises the preparation of a pesticide.
7. The use according to claim 6, wherein the pesticide-repressed pathogenic bacteria comprise phytophthora infestans.
8. The use according to claim 6, characterized in that the pesticide is a formulation made of the isoeugenol with suitable excipients or the pesticide is a formulation made of the methylisoeugenol with suitable excipients;
the preparation is a soluble agent, a water dispersible granule, an aqueous emulsion or a wettable powder.
9. The use according to claim 8, wherein the pesticide is a soluble solution; in the soluble agent, the weight percentage of isoeugenol or methyl isoeugenol is 0.3 percent, and the application dosage of the pesticide is 90-120 milliliters/mu.
10. The use according to claim 8, wherein the pesticide is an aqueous emulsion; in the aqueous emulsion, the weight percentage of isoeugenol or methyl isoeugenol is 20 percent, and the application dosage of the pesticide is 30-45 milliliters per mu.
11. The use according to claim 8, wherein the adjuvant comprises a pesticide carrier and a pesticide adjuvant;
the pesticide carrier is a liquid carrier or a solid carrier, the liquid carrier is deionized water, distilled water or tap water, and the solid carrier is one or more selected from kaolin, bentonite, diatomite, calcium carbonate, white carbon black and attapulgite;
the pesticide auxiliary agent is one or more selected from emulsifying agent, dispersing agent, wetting agent, thickening agent, defoaming agent, oxidant, antifreezing agent, disintegrating agent and filler.
12. A method for controlling plant diseases by using isoeugenol and methyl isoeugenol, which is characterized in that the isoeugenol or the methyl isoeugenol is applied to the stem and leaf, the root or the plant seeds of plants in a sterilization effective amount by spraying, root application or seed coating; the plant diseases are potato late blight and/or tomato late blight, and pathogenic bacteria of the plant diseases are phytophthora infestans.
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| FR2786664B1 (en) * | 1998-12-03 | 2001-03-09 | Xeda Internat Sa | PROCESS FOR THE TREATMENT OF FRUITS AND VEGETABLES USING EUGENOL AND / OR ISOEUGENOL AND USE OF A COMPOSITION BASED ON EUGENOL AND / OR ISOEUGENOL |
| CN101584316A (en) * | 2009-05-27 | 2009-11-25 | 江苏省农业科学院 | Soluble eugenol solvent, preparation method and application thereof |
| CN101843239A (en) * | 2010-05-21 | 2010-09-29 | 江苏省农业科学院 | New eugenol pesticide preparation and application thereof |
| FR2967553B1 (en) * | 2010-11-24 | 2013-06-28 | Xeda International | NEW PROCESS FOR TREATING PLANT PRODUCTS BEFORE OR AFTER HARVESTING WITH PHOSPHONIC ACID AND ROOT OIL |
| CN106508981A (en) * | 2016-10-31 | 2017-03-22 | 福建省农业科学院植物保护研究所 | Clove plant bactericide and application of clove plant bactericide in prevention and treatment of crop diseases |
| KR102653110B1 (en) * | 2019-01-31 | 2024-04-01 | 경북대학교 산학협력단 | Composition for controlling plant diseases comprising Boesenbergia pulcherrima extract |
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