CN111387195A - Method for preventing and treating plant powdery mildew - Google Patents
Method for preventing and treating plant powdery mildew Download PDFInfo
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- CN111387195A CN111387195A CN202010319328.5A CN202010319328A CN111387195A CN 111387195 A CN111387195 A CN 111387195A CN 202010319328 A CN202010319328 A CN 202010319328A CN 111387195 A CN111387195 A CN 111387195A
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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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/44—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom three- or four-membered rings
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Abstract
The invention provides a method for controlling plant powdery mildew, which comprises applying L-azetidine-2-carboxylic acid or an agriculturally and pharmaceutically acceptable salt thereof to the plants, and surprisingly, the L-azetidine-2-carboxylic acid compound provided by the invention has excellent control effect on the plant powdery mildew, particularly on melon powdery mildew.
Description
Technical Field
The invention belongs to the field of plant disease control, and particularly relates to a method for controlling plant powdery mildew, in particular to application of L-azetidine-2-carboxylic acid or agriculturally and pharmaceutically acceptable salts thereof to control plant powdery mildew.
Background
Plant powdery mildew is a plant disease widely existing in plants worldwide, such as wheat, melon, strawberry, grape and flowers, such as Chinese rose, and at present, a common disease particularly in Cucurbitaceae (Cucurbitaceae) vegetables causes serious loss to cucumbers, melons and the like. It is shown by the relevant data that infection of plants with powdery mildew during flowering and fruiting may lead to substantial yield loss.
Powdery mildew mainly damages leaves and can also infect stems and petioles. At the early stage of the disease, the accumulation of white powder consisting of hyphae and conidia on the leaf surface, petiole and caulicle was visually observed. Under appropriate environmental conditions, pathogenic fungi can spread over the entire leaf surface as the disease progresses. Powdery mildew pathogenic bacteria absorb the nutrition of the plant, reduce its photosynthesis, cause the leaves to become chlorosis and even withered, and in severe cases even cause the death of the whole plant. Although the fruits of the plants are rarely directly attacked by the pathogenic bacteria of powdery mildew, the fruits develop malformation and spot formation due to the limited growth caused by the premature senility of the leaves of the infected plants, and finally the yield and the quality are reduced.
The main control measures at present include biological control and chemical control, for example, by selecting disease-resistant varieties and strengthening field management, or spraying chemical pesticides after removing severely infected leaves at the early stage of disease onset. However, the powdery mildew has high reproduction rate and repeated infection, and most systemic bactericides have single action site, so that the germs are easy to generate drug resistance, the dosage is increased by times, the problems of environmental pollution and food safety are caused, and the harm is caused to non-target organisms. The long-term use of chemical pesticides has caused the powdery mildew to almost simultaneously generate drug resistance to benzimidazoles, organophosphates, hydroxypyrimidines, methoxy acrylates, triazoles, phenoxyquinolines and the like[1]。
L-azetidine-2-carboxylic acid is a substance with strong biological activity existing in various natural products, and because its structure is similar to L-proline, L-azetidine-2-carboxylic acid is currently used for modification of polypeptide structure and preparation of many inhibitors, such as hepatic fibrosis inhibitors, algae growth inhibitors, etc. for example, prior art Biologicalactivity of l-2-azoticatechoxylic acid, isolated from polyglutamate odor, pluralize, againt sealed crop plant organism discloses L-azetidine-2-carboxylic acid having activity of inhibiting algae, and prior art of chemical purification on The enzymology of chemical composition of nuclear plant, W L84811 discloses that azetidine carboxylic acid W L84811 can be used as an annual sterile agent, etc. however, no excellent effect is found for controlling powdery mildew, and particularly, it is not reported that it has excellent effect for controlling powdery mildew, and thus, it is not reported that it has excellent effect for controlling powdery mildew of wheat, but it is applied to The plant diseases of wheat-2-3-azetidine.
Disclosure of Invention
The invention aims to overcome the condition that powdery mildew almost has drug resistance to a large number of chemical pesticides, such as benzimidazoles, organophosphates, hydroxypyrimidines, methoxy acrylates, triazoles, phenoxy quinolines and the like in the prior art, and provides a method for more effectively preventing and treating plant powdery mildew, and the invention is completed based on the surprising discovery that L-azetidine-2-carboxylic acid compounds can effectively prevent and treat plant powdery mildew.
In one aspect, the present invention provides a method of controlling powdery mildew in plants, comprising applying to said plants an effective amount of L-azetidine-2-carboxylic acid, or an agriculturally pharmaceutically acceptable salt thereof.
In one embodiment, the agriculturally acceptable salts include inorganic and organic salts.
In one embodiment, the inorganic salt comprises at least one of ammonium, lithium, sodium, potassium, cesium, calcium, magnesium, copper, aluminum, zinc, barium, and quaternary ammonium salts.
In one embodiment, the organic salt comprises at least one of arginine, t-butylamine, dimethylamine, diethanolamine, ethanolamine, ethylenediamine, imidazole, lysine, methylamine, pyridine, picolinate, piperazine, triethylamine, triethanolamine, trimethylamine, and urea salts.
In one embodiment, the plant is a barley, wheat, strawberry, grape, rose, apple, rubber or melon plant. Further, the plant is preferably a melon plant.
In one embodiment, the melon plant is cucumber, melon, balsam pear, wax gourd, pumpkin, luffa, hami melon or cucurbita pepo.
In one embodiment, the L-azetidine-2-carboxylic acid, or an agriculturally pharmaceutically acceptable salt thereof, is formulated as a pesticide formulation.
In one embodiment, the pesticide formulation is at least one of an aqueous agent, a dust, a granule, a wettable powder, and a soluble powder.
In one embodiment, the pesticide formulation is configured for use as a spray and the L-azetidine-2-carboxylic acid, or an agriculturally pharmaceutically acceptable salt thereof, is present in the spray in an amount of 20-2000 μ g/m L in a preferred embodiment, the L-azetidine-2-carboxylic acid, or an agriculturally pharmaceutically acceptable salt thereof, is present in the spray in an amount of 50-200 μ g/m L.
In another aspect, the invention also provides the use of L-azetidine-2-carboxylic acid, or an agriculturally pharmaceutically acceptable salt thereof, for controlling powdery mildew in plants.
After research, the L-azetidine-2-carboxylic acid compound provided by the invention has excellent control effects on various plant powdery mildews, such as wheat powdery mildew, barley powdery mildew, strawberry powdery mildew, grape powdery mildew, Chinese rose powdery mildew, apple powdery mildew, rubber powdery mildew and melon powdery mildews, wherein the control effects on melon powdery mildews are particularly excellent.
Detailed Description
The following describes in detail specific embodiments of the present invention. It should be understood that the detailed description and specific examples, while indicating the present invention, are given by way of illustration and explanation only, not limitation.
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and such ranges or values should be understood to encompass values close to those ranges or values. For ranges of values, between the endpoints of each of the ranges and the individual points, and between the individual points may be combined with each other to give one or more new ranges of values, and these ranges of values should be considered as specifically disclosed herein.
Before describing the present invention in detail, it is to be understood that the terminology used herein is for the purpose of describing particular embodiments only, and is not intended to limit the scope of the present invention which will be limited only by the appended claims. For a more complete understanding of the invention described herein, the following terms are used, and their definitions are set forth below. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
The term "agriculturally acceptable" as used herein refers to a substance that does not affect the biological activity or properties of the compounds of the present invention and is relatively non-toxic, i.e., the substance may be administered to an individual without causing an undesirable biological response or interacting in an undesirable manner with any of the components included in the composition. In the present invention, the "agriculturally and pharmaceutically acceptable salt" may include inorganic salts and organic salts, wherein the organic salt may include, but is not limited to, ammonium, lithium, sodium, potassium, cesium, calcium, magnesium, copper, aluminum, zinc, barium, or quaternary ammonium salt, and the inorganic salt may include, but is not limited to, arginine, tert-butylamine, dimethylamine, diethanolamine, ethanolamine, ethylenediamine, imidazole, lysine, methylamine, pyridine, picolinate, piperazine, triethylamine, triethanolamine, trimethylamine, or urea salt.
The term "effective amount" as used herein refers to the amount of a controlling agent that confers a controlling effect on a plant to be controlled at a reasonable benefit/risk ratio applicable to the control of any agent. In some embodiments, an "effective amount" refers to an amount of a therapeutic agent or composition that is effective to treat, ameliorate or prevent (e.g., delay onset of) an associated disease or condition and/or exhibit a detectable therapeutic or prophylactic effect, such as by ameliorating symptoms associated with the disease, preventing or delaying the onset of the disease, and/or also reducing the severity or frequency of symptoms of the disease.
L-azetidine-2-carboxylic acid, also known as (S) -azetidine-2-carboxylic acid, was referred to in the present invention as L-Aze.1955, Fowden isolated from a 70% ethanol extract of fresh leaves and seeds of the plant, Convallaria majalis, the first natural ammonia with azetidine structure to be found in plantsAmino acid[2]。
As is currently known, L-azetidine-2-carboxylic acid is present in the Liliaceae (L iliaceae), the Leguminosae (L egulinaceae) Fenghuang (Delonix regia) and peltate (Peltophorum pterocarpum), red algae and sugar beet (Beta vulgaris)[2,3]。
In recent years, chemists have conducted extensive studies on the method for mass production of L-azetidine-2-carboxylic acid, and mainly have the following synthetic routes, (1) using gamma-butyrolactone as a raw material, (2) using L-N-methylsulfonyl-methionine as a raw material, (3) using methyl 4-amino-2-hydroxybutyrate as a raw material, (4) using α -methylaniline as a raw material, and (5) using L-aspartic acid as a raw material.
In 2009, Bouazaoui et al cyclized L-azetidine-2-carboxylic acid by two methods using L-2-amino-4-hydroxybutyric acid tert-butyl ester 2 obtained by reduction of protected L-aspartic acid as a raw material[4]The method has simple steps, is green and safe, has high efficiency and high yield, and is an effective method for synthesizing the natural product L-azetidine-2-carboxylic acid.
In 2012, Jin and Zhang used 1, 3-dibromo compound and benzhydrylamine as raw materials, and passed through SN2The intermolecular nucleophilic substitution reaction synthesizes the optically pure (S) -azetidine-2-carboxylic acid 15]The method is a novel method for synthesizing an optically pure natural product L-azetidine-2-carboxylic acid, and has certain potential of industrial application, but the price of benzhydrylamine is slightly expensive.
L-azetidine-2-carboxylic acid is a substance having a strong biological activity which is present in many natural products, its four-membered ring specific amino acid structure is similar to that of L-proline which constitutes a natural protein L-azetidine-2-carboxylic acid shows an activity in vivo precisely because of this structural similarity, and in the process of forming a protein chain, the two substances compete with each other, thereby interfering with the normal metabolism of L-proline and causing a series of changes in the organism.
Since the structure of L-azetidine-2-carboxylic acid is similar to L-proline, L-azetidine-2-carboxylic acid is often applied to modification of polypeptide structure and preparation of many inhibitors, such as hepatic fibrosis inhibitors, algae growth inhibitors, and the like, in addition, L-azetidine-2-carboxylic acid is commonly used to construct organic chiral catalysts due to the rigid structure of its four-membered ring, and is widely applied to multiple fields in asymmetric synthesis, such as asymmetric addition reaction of ketone and alkyne, asymmetric Michael addition reaction, asymmetric cyclopropanation reaction, asymmetric Diels-Alder reaction, and the like, however, L-azetidine-2-carboxylic acid compounds are not reported to be used for preventing and treating plant powdery mildew at present.
In one aspect, the present invention provides a method of controlling powdery mildew in plants, comprising applying to said plants an effective amount of L-azetidine-2-carboxylic acid, or an agriculturally pharmaceutically acceptable salt thereof.
According to the present invention, the agriculturally pharmaceutically acceptable salt may be any agriculturally pharmaceutically acceptable salt commonly found in the art. For example, in one embodiment, the agriculturally pharmaceutically acceptable salts may include inorganic and organic salts. More specifically, the inorganic salt may include at least one of ammonium, lithium, sodium, potassium, cesium, calcium, magnesium, copper, aluminum, zinc, barium, and quaternary ammonium salts, and the organic salt may include at least one of arginine, tert-butylamine, dimethylamine, diethanolamine, ethanolamine, ethylenediamine, imidazole, lysine, methylamine, pyridine, picolinate, piperazine, triethylamine, triethanolamine, trimethylamine, and urea salts, but is not limited thereto. That is, the agriculturally acceptable salt in the present invention may specifically be any of the above agriculturally acceptable salts alone, or any combination thereof.
In addition, the relevant data show that the powdery mildew is particularly serious in plants suffering from powdery mildew, and the melon plants infected with the powdery mildew at the flowering and fruiting stages can cause yield reduction by 20-40%. Thus, in an embodiment, the plant may in particular be a barley, wheat, strawberry, grape, rose, apple, rubber or melon plant, more in particular the melon plant may more in particular be cucumber, melon, balsam pear, wax gourd, pumpkin, luffa, hami melon or pumpkin, etc.
According to the present invention, L-azetidine-2-carboxylic acid, or an agriculturally pharmaceutically acceptable salt thereof, applied may take a wide range of forms, such as various common dosage forms in the art in one embodiment, the L-azetidine-2-carboxylic acid, or an agriculturally pharmaceutically acceptable salt thereof, may be formulated as desired into corresponding pesticidal formulations, such as aqueous, dust, granules, wettable powders or soluble powders, and may be further formulated as a spray at the time of use so as to be applied to the plants to be controlled in a manner of coating or spraying, preferably, the L-azetidine-2-carboxylic acid, or agriculturally pharmaceutically acceptable salt thereof, may be present in the spray in an amount of 20 to 2000 μ g/m L1, such as 80 μ g/m L, 100 μ g/m 2, 120 μ g/m L, 300 μ g/m L, 500 μ g/m L, 1000 μ g/m L, or 1800 μ g/m L, etc., more preferably in an amount of 20 to 2000 μ g/m L.
Furthermore, L-azetidine-2-carboxylic acid, or an agriculturally acceptable salt thereof, of the present invention may also be applied to the plant separately, sequentially or simultaneously with other powdery mildew resistant agents, such as imidazoles, organophosphates, hydroxypyrimidines, methoxypropenes, triazoles and phenoxyquinolines, and more specifically, tebuconazole, to prevent powdery mildew.
In another aspect, the invention also provides L-azetidine-2-carboxylic acid or an agriculturally pharmaceutically acceptable salt thereof for controlling plant powdery mildew, wherein the use mode of the use can be carried out by referring to the method for controlling plant powdery mildew, and the specific scheme can be the same as that described above and is not repeated herein.
After research, the L-azetidine-2-carboxylic acid compound provided by the invention has excellent control effects on various plant powdery mildews, such as wheat powdery mildew, barley powdery mildew, strawberry powdery mildew, grape powdery mildew, Chinese rose powdery mildew, apple powdery mildew, rubber powdery mildew and melon powdery mildews, and particularly has excellent control effects on melon powdery mildews.
Hereinafter, the effect of L-azetidine-2-carboxylic acid of the present invention on controlling plant powdery mildew will be described in detail by way of examples.
Examples
In the examples, the plant seeds used were purchased from Shao agricultural development Co., Ltd, and the control effect of L-azetidine-2-carboxylic acid compounds on powdery mildew of plants was measured by the following method:
adding seedling raising matrix into a plastic flowerpot, sowing three plant seeds in each pot, placing the pot in a greenhouse at the temperature of about 25 ℃ for culturing after watering thoroughly, and performing a development test when the cotyledon is fully developed and the 1 st true leaf is just exposed (about 10 days). When the cotyledons of the plant seedlings are fully unfolded, uniformly brushing powdery mildew conidia on the diseased plant leaves by using a writing brush on healthy plant seedlings, culturing in a greenhouse at about 25 ℃, and periodically preserving and propagating strains on new plants for later use. Then, the compounds to be tested were prepared to the required concentration with 0.05% tween-20 aqueous solution, and sprayed onto the prepared plants, wherein tebuconazole was used as the positive control group, 0.05% tween-20 aqueous solution was used as the blank control group, each group contained 9 plants, and the average value was calculated. And (5) after culturing for 7-8 d, investigating the damage level and the number of the cotyledons of each treated plant according to the following standards, and calculating the disease index and the prevention and treatment effect.
Reference to classification methods[6]。
Level 0: no disease spots;
level 1: the lesion area accounts for less than 5% of the whole leaf area;
and 3, level: the lesion area accounts for 6 to 10 percent of the whole leaf area;
and 5, stage: the lesion area accounts for 11 to 20 percent of the whole leaf area;
and 7, stage: the lesion area accounts for 21-40% of the whole leaf area;
and 9, stage: the lesion area accounts for more than 40% of the whole leaf area.
∑ (disease index) (× relative grade value of each grade of diseased leaf number)/(× 9 total leaf number investigation) × 100
The prevention and treatment effect is × 100 percent (blank control disease index-treatment disease index)/blank control disease index
Example 1 controlling Effect of 1L-azetidine-2-carboxylic acid on cucumber powdery mildew
In this embodiment, cucumbers are selected as plants to be tested, and the control effects of L-azetidine-2-carboxylic acid, D-azetidine-2-carboxylic acid and azetidine-3-carboxylic acid on cucumber powdery mildew at the same concentration are compared, and the results are shown in table 1 below, it can be seen from the results in table 1 that the control effect of azetidine-3-carboxylic acid is similar to that of the blank control group, that is, the control effect on cucumber is almost not achieved, D-azetidine-2-carboxylic acid has a weak powdery mildew control effect, whereas L-azetidine-2-carboxylic acid of the present invention has a control effect as high as about 84%, which is stronger than about 62% of tebuconazole of the positive control group.
TABLE 1
EXAMPLE 2 prevention and treatment Effect of L-azetidine-2-carboxylic acid on cucumber powdery mildew at different concentrations
In the embodiment, cucumbers are selected as plants to be tested, the control effects of L-azetidine-2-carboxylic acid on cucumber powdery mildew at different concentrations are compared, and the results are shown in the following table 2. from the results in table 2, it can be seen that the control effect is gradually enhanced with the increase of the concentration of L-azetidine-2-carboxylic acid, and the control effect reaches about 97% at a concentration of 200 μ g/m L, which is obviously higher than about 68% of the control effect of tebuconazole of a positive control group with the same concentration.
TABLE 2
Example 3 controlling Effect of 3L-azetidine-2-carboxylic acid on melon powdery mildew
In this example, melons were selected as plants to be tested, and the control effects of L-azetidine-2-carboxylic acid, D-azetidine-2-carboxylic acid and azetidine-3-carboxylic acid on cucumber powdery mildew at the same concentrations were compared, and the results are shown in table 3 below, it can be seen from the results in table 3 that the control effect of azetidine-3-carboxylic acid is similar to that of the blank control group, i.e., the control effect on powdery mildew is almost not achieved on melons, and D-azetidine-2-carboxylic acid has a weaker control effect on powdery mildew, whereas L-azetidine-2-carboxylic acid of the present invention has a control effect as high as about 83%, which is stronger than about 64% of tebuconazole of the positive control group.
TABLE 3
Example 4 controlling Effect of 4L-azetidine-2-carboxylic acid on powdery mildew of pumpkin
In this embodiment, cucurbita pepo is selected as a plant to be tested, and the control effects of L-azetidine-2-carboxylic acid, D-azetidine-2-carboxylic acid and azetidine-3-carboxylic acid on cucumber powdery mildew at the same concentration are compared, and the results are shown in table 4 below, it can be seen from the results in table 4 that the control effect of azetidine-3-carboxylic acid is similar to that of the blank control group, that is, the control effect on powdery mildew is hardly achieved on cucurbita pepo, and the control effect of D-azetidine-2-carboxylic acid is weaker, whereas L-azetidine-2-carboxylic acid of the present invention has the control effect as high as about 86%, and is stronger than about 65% of tebuconazole of the positive control group.
TABLE 4
The preferred embodiments of the present invention have been described in detail, however, the present invention is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solution of the present invention within the technical idea of the present invention, and these simple modifications are within the protective scope of the present invention.
It should be noted that the various technical features described in the above embodiments can be combined in any suitable manner without contradiction, and the invention is not described in any way for the possible combinations in order to avoid unnecessary repetition.
In addition, any combination of the various embodiments of the present invention is also possible, and the same should be considered as the disclosure of the present invention as long as it does not depart from the spirit of the present invention.
Reference to the literature
[1] The biological prevention and treatment research of powdery mildew of melons is developed by Buxus, Zhuhaiyun, Libo, and the like [ J ]. J.J.Microbiol.2016, 36(01): 106-.
[2]Fowden L.Azetidine-2-carboxylic acid:a new cyclic imino acidoccurring in plants[J].The Biochemical journal.1956,64(2):323-332.
[3]Rubenstein E,Zhou H,Krasinska K M,et al.Azetidine-2-carboxylicacid in garden beets(Beta vulgaris)[J].Phytochemistry.2006,67(9):898-903.
[4]Bouazaoui M,Martinez J,Cavelier F.Direct Access to L-Azetidine-2-carboxylic Acid[J].European Journal of Organic Chemistry.2009,2009(17):2729-2732.
[5]Jin J Z,Zhang J.Synthesis of L-Azetidine-2-Carboxylic Acid[J].Advanced Materials Research.2012,455-456:635-638.
[6] The pesticide field efficacy test criterion (I) is that the bactericide prevents and treats cucumber powdery mildew, GB/T17980.30-2000.
Claims (10)
1. A method of controlling powdery mildew of a plant comprising applying to said plant an effective amount of L-azetidine-2-carboxylic acid, or an agriculturally pharmaceutically acceptable salt thereof.
2. The method of claim 1, wherein the agriculturally pharmaceutically acceptable salt comprises an inorganic salt and an organic salt.
3. The method of claim 2, wherein the inorganic salt comprises at least one of ammonium, lithium, sodium, potassium, cesium, calcium, magnesium, copper, aluminum, zinc, barium, and quaternary ammonium salts.
4. The method of claim 2, wherein the organic salt comprises at least one of arginine, t-butylamine, dimethylamine, diethanolamine, ethanolamine, ethylenediamine, imidazole, lysine, methylamine, pyridine, picolinate, piperazine, triethylamine, triethanolamine, trimethylamine, and urea salts.
5. The method of claim 1, wherein the plant is barley, wheat, strawberry, grape, rose, apple, rubber or melon.
6. The method of claim 5, wherein the melon plant is cucumber, melon, balsam pear, wax gourd, pumpkin, luffa, hami melon, or pumpkin.
7. The method of claim 1, wherein said L-azetidine-2-carboxylic acid, or an agriculturally-pharmaceutically acceptable salt thereof, is formulated as a pesticide formulation.
8. The method of claim 7, wherein the pesticide formulation is at least one of an aqueous agent, a dust, a granule, a wettable powder, and a soluble powder.
9. The method of claim 7 or 8, wherein the pesticide formulation is configured as a spray for use and the L-azetidine-2-carboxylic acid, or an agriculturally pharmaceutically acceptable salt thereof, is present in the spray in an amount of 20-2000 μ g/m L.
Use of L-azetidine-2-carboxylic acid, or an agriculturally pharmaceutically acceptable salt thereof, for controlling powdery mildew of plants.
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| CN111972442A (en) * | 2020-08-19 | 2020-11-24 | 吴文君 | Method for preventing and treating plant powdery mildew by using polygonatum sibiricum extract |
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|---|---|---|---|---|
| EP2524597B1 (en) * | 2010-01-13 | 2016-03-16 | Ajinomoto Co., Inc. | Use of an agent for enhancing resistance to disease of cucurbitaceae plant and a method for controlling plant disease using the agent |
| CN109053529A (en) * | 2018-08-09 | 2018-12-21 | 吴文君 | L-Glutimic acid metal complex and its preparation method and application |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2524597B1 (en) * | 2010-01-13 | 2016-03-16 | Ajinomoto Co., Inc. | Use of an agent for enhancing resistance to disease of cucurbitaceae plant and a method for controlling plant disease using the agent |
| CN109053529A (en) * | 2018-08-09 | 2018-12-21 | 吴文君 | L-Glutimic acid metal complex and its preparation method and application |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111972442A (en) * | 2020-08-19 | 2020-11-24 | 吴文君 | Method for preventing and treating plant powdery mildew by using polygonatum sibiricum extract |
| CN111972442B (en) * | 2020-08-19 | 2021-09-14 | 吴文君 | Method for preventing and treating plant powdery mildew by using polygonatum sibiricum extract |
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