CN117859751A - Application of 1-hydroxy-2-piperidinecarboxylic acid in preventing and treating citrus yellow dragon disease and/or green mold - Google Patents

Application of 1-hydroxy-2-piperidinecarboxylic acid in preventing and treating citrus yellow dragon disease and/or green mold Download PDF

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Publication number
CN117859751A
CN117859751A CN202311865947.4A CN202311865947A CN117859751A CN 117859751 A CN117859751 A CN 117859751A CN 202311865947 A CN202311865947 A CN 202311865947A CN 117859751 A CN117859751 A CN 117859751A
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hydroxy
piperidinecarboxylic acid
nhp
citrus
yellow dragon
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徐强
路志浩
胡斌
原涛
徐远涛
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Hubei Hongshan Laboratory
Huazhong Agricultural University
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Hubei Hongshan Laboratory
Huazhong Agricultural University
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01GHORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
    • A01G13/00Protecting plants
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01GHORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
    • A01G7/00Botany in general
    • A01G7/06Treatment of growing trees or plants, e.g. for preventing decay of wood, for tingeing flowers or wood, for prolonging the life of plants
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40Biocides, 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
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01PBIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00Disinfectants; Antimicrobial compounds or mixtures thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01PBIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00Fungicides

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  • Life Sciences & Earth Sciences (AREA)
  • Environmental Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Forests & Forestry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Ecology (AREA)
  • Health & Medical Sciences (AREA)
  • Biodiversity & Conservation Biology (AREA)
  • Microbiology (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Mycology (AREA)
  • Botany (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention discloses application of 1-hydroxy-2-piperidinecarboxylic acid in preventing and treating citrus yellow dragon disease or/and penicilliosis, wherein the effective antibacterial concentration of NHP in the application is more than or equal to 300 mug/mL. The invention verifies that NHP has obvious inhibiting effect on the content of yellow dragon germ and penicillium germ by injecting the solution containing NHP into yellow dragon disease leaves and inoculating penicillium after treating mature citrus fruits. Meanwhile, NHP is a natural metabolite synthesized by plants, and has stronger safety compared with the existing chemical bactericides or antibiotic bactericides.

Description

Application of 1-hydroxy-2-piperidinecarboxylic acid in preventing and treating citrus yellow dragon disease and/or green mold
Technical Field
The invention relates to the field of biological control of citrus, in particular to application of 1-hydroxy-2-piperidinecarboxylic acid in control of citrus yellow dragon disease or/and blue mold.
Background
Citrus is one of the most important cultivated fruit trees in the world, and after more than 60 years of development, the yield of Chinese citrus is increased from the first 180 kilotons to 43540 kilotons in 2019, the yield is the first in the world, and more than one hundred varieties are bred. However, various citrus diseases have been limiting the development of the citrus industry. In the cultivation process, the yellow dragon disease almost causes destructive damage to the citrus, and once the disease tree is only eradicated by the root, no citrus resource capable of resisting the yellow dragon disease is found at present.
Yellow dragon disease is a disease caused by gram-negative bacteria (Candidatus Liberibacter asiaticus, CLas), is mainly transmitted through psyllium, and yellow dragon bacteria cannot be stably cultured for a long time at present and are transmitted to about 50 countries and regions, so that great threat is caused to the development of world citrus, and the development of yellow dragon disease-resistant metabolites is an advantageous choice for solving the problem due to the lack of resistant citrus resources. Penicillium is the main fungus responsible for post-harvest penicillium of citrus, and some chemical coating agents are currently used for preventing and treating post-harvest penicillium of citrus. Some of the film coating agents have the effect of inhibiting the penicilliosis through direct bacteriostasis, and some of the film coating agents improve the capability of resisting the penicilliosis through forming a layer of physical barrier, but the safety and the effect are different, so that the selection scheme of bacteriostasis after the orange is picked can be increased by developing natural bacteriostasis metabolites, and the food safety is effectively improved.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides an application of 1-hydroxy-2-piperidinecarboxylic acid in preventing and treating citrus yellow dragon disease or/and green mold. The 1-hydroxy-2-piperidinecarboxylic acid is a metabolite synthesized by a plant from lysine in the body, and is green and efficient. The NHP developed by the invention can inhibit the Penicillium citrinum and the yellow dragon germ, and has important value for preventing and controlling the yellow dragon disease and the blue mold and recovering the loss of the citrus industry.
In order to achieve the above purpose, the technical scheme of the invention is as follows:
the invention provides an application of 1-hydroxy-2-piperidinecarboxylic acid (NHP) in preventing and treating citrus yellow dragon disease or/and penicilliosis, wherein the chemical formula of the 1-hydroxy-2-piperidinecarboxylic acid (NHP) is as follows:
the invention also provides application of the 1-hydroxy-2-piperidinecarboxylic acid (NHP) in preparing a bacteriostatic agent for preventing and treating citrus yellow dragon disease or/and green mold.
The invention also provides a bacteriostatic agent for preventing and treating citrus yellow dragon disease or/and penicilliosis, which contains 1-hydroxy-2-piperidinecarboxylic acid (NHP), wherein the concentration of the 1-hydroxy-2-piperidinecarboxylic acid is more than or equal to 300 mug/mL.
Further, the concentration of 1-hydroxy-2-piperidinecarboxylic acid is effectively 500 to 1000. Mu.g/ml.
The invention also provides a method for inhibiting the yellow dragon disease: the method is to inject the bacteriostat into the disease tree through a leaf injection mode.
Further, the method comprises the following specific steps: when the citrus leaves are ill, the small holes are punctured by the needle heads on the back surfaces of the diseased leaves, and the mesophyll cells are filled with a bacteriostat through a syringe, wherein the effective concentration of the 1-hydroxy-2-piperidinecarboxylic acid in the bacteriostat is 500-1000 mug/mL.
The invention also provides a method for inhibiting the penicilliosis, which is carried out by needling the pericarp through a small hole and then absorbing the bacteriostatic agent through the small hole.
Further, the method comprises the following specific steps: after the citrus fruits are picked, a small hole with the depth of 1mm is respectively pricked at the two sides of the fruits by an inoculating needle, 5 mu l of bacteriostatic agent is sucked and dripped at the small hole, the bacteriostatic agent can be absorbed after about 1.5 hours, the periphery of the small hole has obvious inhibition effect on inoculated penicillium, and the effective concentration of 1-hydroxy-2-piperidinecarboxylic acid in the bacteriostatic agent is 500-1000 mu g/mL. The invention has the beneficial effects that:
according to the invention, the NHP can be reduced by more than 70% by injecting the NHP on citrus leaves infected with the yellow-shoot germ. NHP is a natural metabolic substance synthesized by plants themselves to maintain systemic immunity, and the safety is obviously higher than that of other antibiotics for inhibiting the yellow shoot germ. Meanwhile, the invention proves that the NHP has a direct sterilization effect for the first time.
Drawings
FIG. 1 is a graph showing the bacteriostatic effect of injection of 500 μg/mL NHP and control DMSO in leaves of Huanglongbing tree;
in the figure, A is a change condition diagram of yellow dragon bacteria after injection of 500 mug/mL NHP for 7 d;
b is a change condition diagram of the yellow dragon bacteria after the DMSO is injected into the control group for 7 d;
c is a graph for calculating the antibacterial efficiency of 500 mug/ml NHP to yellow dragon bacteria by taking COX as an internal reference gene;
* Significant differences in P <0.01 levels are indicated, and no significant differences are indicated by n.s.
FIG. 2 is a graph showing the screening effect of the optimal inhibitory concentration of the metabolite NHP of yellow-tailed bacteria;
in the graph, A is a graph for inhibiting the yellow dragon germs after NHP with different concentration gradients is selected to be injected into leaves of the yellow dragon disease tree, and Ct value rising degree is used as a measurement index;
b is a change trend graph of Ct value after NHP with different concentration gradients is injected into leaves of the yellow dragon disease;
* Indicating that there was a significant difference in P <0.05 level and n.s indicating that there was no significant difference.
FIG. 3 is a graph showing the inhibitory effect of NHP on Penicillium citrinum;
in the figure, A is a plaque area map of NHP treated group and control group;
b is a plot of plaque growth status in NHP treated and control groups;
* Indicating significant differences in P <0.05 levels, x indicating significant differences in P <0.01 levels, and n.s indicating no significant differences.
FIG. 4 is a graph showing the concentration of NHP inhibitory to Penicillium species and other inhibitory substances;
in the figure, A is a graph of the inhibition effect of NHP with different concentrations on penicillium;
b is a comparison graph of antibacterial effects of 1000 mug/mL NHP, prochloraz and terbinafine.
FIG. 5 is a graph showing the effect of bacteriostatic agent 1 on the inhibition of penicillium from post-harvest citrus fruits;
in the figure, A is a graph of the influence degree of the bacterial inhibitor 1 and water (control) on the disease state of the fruits after the fruits are treated respectively and inoculated with penicillium;
b is a measurement result of the diameter of the lesion in the graph A, and each lesion is measured by a crisscross method;
* Indicating significant differences in P <0.001 levels.
Detailed Description
The present invention is described in further detail below in conjunction with specific embodiments for understanding by those skilled in the art.
Example 1 1 inhibition of citrus yellow dragon by hydroxy-2-piperidinecarboxylic acid (NHP)
1. Experimental materials:
1) A compound: 1-hydroxy-2-piperidinecarboxylic acid, available from Beijing Yibo cloud technology Co.
2) Biological material: orange plants infected with yellow dragon disease.
2. Experimental procedure
1) Detection of bacterial content in yellow dragon disease tree
The yellow dragon disease tree with stable bacteria is selected as a test material (the yellow dragon disease pathogenic bacteria is Candidatus Liberibacter asiaticus). The bacterial load is detected by using a Real-time qPCR method, the detection primer is from the 16S rRNA gene of CLas, and the reference gene is the mitochondrial gene of citrus: cytochrome Oxidase (COX). The CT value reflects the biomass of CLas, with smaller CT values indicating greater biomass. COX is used to check whether DNA mass and initial DNA concentration are comparable.
2) Configuration of NHP
NHP was formulated as working solution at a final concentration of 500. Mu.g/ml with water or dimethyl sulfoxide (DMSO), and DMSO was used as control.
3) Antibacterial metabolite injection infected leaf
3 stable, bacteria-bearing orange plants were selected, each with a total of 4 leaves selected at different orientations. Two holes are respectively drilled on two sides of a vein by a puncher before injection, two cut leaves are taken as one sample, and the sample is placed into a 2mL centrifuge tube containing a sampling steel ball to be used as a 0d control. Then, NHP was injected on one side of the veins of the selected leaf, and DMSO was injected on the other side. On day 7 after injection, two holes were punched on each side of the leaf blade injected with DMSO and NHP, respectively, and 2 removed leaves were repeated and placed in a 2ml centrifuge tube with steel balls.
4) NHP antibacterial effect detection
DNA extraction was performed on the samples 0d and 7d after injection collected in step 3), and the extraction method used a CTAB method. The DNA concentration was adjusted to a concentration range of 100-150ng/ul after extraction. Then, quantitative Mix with probe (HieffqPCR TaqMan Probe Master Mix quantitative detection was performed by assist biotechnology (Shanghai) to obtain CT values of samples of 0d and 7d after treatment.
5) Statistics of bacteriostatic effects
The average, error and significance of the CT values for each 12 replicates of 0d and 7d were calculated. Determining the antibacterial effect of NHP on yellow dragon bacteria.
The inhibitory effect of NHP on yellow dragon bacteria is shown in figure 1: in the leaves after NHP treatment, the content of yellow dragon bacteria is obviously reduced, and the CT value is obviously increased; calculation of relative bacterial load using COX as an internal control indicated a 76% decrease in relative bacterial load after 7 days in NHP treated leaves.
Example 21 concentration screening of hydroxy-2-piperidinecarboxylic acid (NHP) for inhibiting citrus yellow dragon disease
NHP working solutions with concentration gradients of 5 mug/ml, 10 mug/ml, 500 mug/ml, 1000 mug/ml, 5000 mug/ml and 10000 mug/ml were selected and respectively injected into different yellow dragon tree leaves according to the method described in step 3 of example 1. Each treatment was injected with 3 trees, totaling more than 8 leaves. The content of yellow shoot bacteria was measured 7 days after injection according to the method described in example 1, step 4.
The results show that the low concentration NHP of 5 mug/ml and 10 mug/ml has no inhibition effect on the yellow dragon bacteria, the inhibition effect of the NHP on the yellow dragon bacteria is obvious at 500 mug/ml, the inhibition effect is equivalent to 500 mug/ml at 1000 mug/ml, and the inhibition effect has obvious difference. Then the antibacterial effect is not greatly improved along with the increase of the concentration, and the antibacterial effect is stable. So the effective antibacterial concentration of NHP to yellow dragon germ is more than or equal to 500 mug/ml.
Example 3 1 inhibition of citrus blue mould by hydroxy-2-piperidinecarboxylic acid (NHP)
1. Experimental materials:
1) A compound: 1-hydroxy-2-piperidinecarboxylic acid, available from Beijing Yibo cloud technology Co.
2) Biological material: penicillium citrinum (Penicillium italicum)
2. Experimental procedure
1) Culture of Penicillium
First, a solid PDA medium was prepared. 200g of fresh potatoes are selected, boiled by clear water, placed into 8 layers of gauze for filtration, 30g of sucrose and 8g of agar are added into the filtrate, the volume is fixed to 1L by water, and the temperature is 121 ℃ and the sterilization is carried out for 15 min. Then evenly pouring the mixture into a 9cm culture dish, so that the solid PDA culture medium in the dish is as smooth as possible. Then picking a piece of penicillium circular bacterial cake stored at-80 ℃ and placing the cake at the center of a PDA culture dish, wherein one side of the bacterial cake with bacteria growth is downward. After 7d of incubation, the spores were suspended in clear water and adjusted to a final concentration of 1.0x10 6 Spores/ml was used as working bacteria solution.
2) Formulation of NHP.
NHP was formulated as 500. Mu.g/ml working solution with water or DMSO, and DMSO was used as the control.
3) Configuration of bacteriostatic culture dish
6 filter paper sheets having a side length of about 1cm x 1cm were cut, and 3 of them were completely wetted with 5ul of NHP working fluid (500. Mu.g/ml). The other 3 sheets were wetted with DMSO solvent. The filter paper with NHP was placed in parallel on the top side of the solid PDA dish and the filter paper with DMSO was placed in parallel on the bottom side of the solid PDA dish.
4) Antibacterial test
5ul of Penicillium spore suspension (1.0X10) was aspirated separately 6 Spore/ml), drop on 6 filter paper sheets in antibacterial culture medium, make marks, and seal culture dishCulturing at 25deg.C, and observing penicillium growth every 12 h. And in the period of obvious difference of the growth areas of the penicillium, timely photographing and recording, adding a scale during photographing, and then calculating the area of the bacterial plaque by using photoshop.
More than 3 bacteriostatic dishes were set up for each experiment as replicates.
5) Statistics of bacteriostatic effects
The penicillium growth area on the filter paper sheets with NHP and DMSO were calculated separately, and the mean, standard deviation and significance were calculated.
As shown in fig. 3: the NHP has obvious inhibition effect on the growth of penicillium, and after the NHP is added, the penicillium growth area can be inhibited to the greatest extent by about 50%.
Example 4 concentration screening of NHP for inhibition of blue mold and comparison with production of commonly used bacteriostat
PDA media containing varying concentrations of NHP were prepared as in Table 1. A5 mm punch was used to circumferentially punch the PDA medium of the normal growth Penicillium as an inoculum cake. The bacterial cake was placed in the center of PDA medium with different concentration of NHP, and cultured for about 3d, and the size of bacterial plaque was observed.
Bacteriostasis% = (negative control growth diameter-NHP treatment growth diameter)/(negative control growth diameter-5) ×100.
In addition, 1000 mug/mL of commercial penicillium fungicide prochloraz and 1000 mug/mL of broad-spectrum fungicide terbinafine are added into the culture medium, and the effects of NHP and the two fungicides are compared.
As can be seen from table 1 and fig. 4A: NHP has obvious bactericidal effect on penicillium citrinum. As can be seen from table 2 and fig. 4B: the NHP has better bactericidal effect than the conventional chemical bactericide terbinafine, which is between terbinafine and prochloraz.
TABLE 1 inhibition of Penicillium by NHP at different concentrations
Note that: the virulence equation is: y=0.2365+1.9471 x, correlation coefficient R 2 =0.9753,EC 50 =279.51μg/mL。
TABLE 2 inhibition of Penicillium by different antibacterial substances
Example 5 bacteriostat 1 for controlling citrus yellow dragon disease or/and penicilliosis,
the bacteriostatic agent 1 contains 1-hydroxy-2-piperidinecarboxylic acid, wherein the effective concentration of the 1-hydroxy-2-piperidinecarboxylic acid is 500 mug/mL.
Example 6 bacteriostatic agent for controlling yellow dragon disease and/or blue mold of citrus
The bacteriostatic agent 2 contains 1-hydroxy-2-piperidinecarboxylic acid, wherein the effective concentration of the 1-hydroxy-2-piperidinecarboxylic acid is 1000 mug/mL.
Example 7 effect of bacteriostatic agent 1 on inhibition of Penicillium in citrus fruit
Picking completely mature susceptible penicillium breed satsuma mandarin orange in the orchard, washing the peel with clear water, and airing. Inoculating needles are used for pricking small holes with the depth of 1mm on two sides of fruits, 5 mu l of the bacteriostatic agent 1 is sucked and dripped into the small holes, the bacteriostatic agent can be absorbed after about 1.5 hours, and then 5 mu l of the penicillium fungus solution is dripped into the small holes dripped with the bacteriostatic agent 1 to serve as fruits of a treatment group. The small holes are firstly dripped with clear water and then dripped with penicillium liquid as a control group. Sealing and moisturizing in a plastic box after inoculation, and observing the growth condition of bacterial plaques for about 3 days.
As can be seen from fig. 5: after the citrus unshiu treated by the bacteriostatic agent 1 is inoculated with penicillium, the area of the disease spots and the disease development process are obviously smaller than those of a control group.
Other parts not described in detail are prior art. Although the foregoing embodiments have been described in some, but not all, embodiments of the invention, it should be understood that other embodiments may be devised in accordance with the present embodiments without departing from the spirit and scope of the invention.

Claims (8)

1. An application of 1-hydroxy-2-piperidinecarboxylic acid in preventing and treating citrus yellow dragon disease or/and penicilliosis, which is characterized in that: the chemical formula of the 1-hydroxy-2-piperidinecarboxylic acid is as follows:
2. application of 1-hydroxy-2-piperidinecarboxylic acid in preparing antibacterial agent for preventing and treating yellow dragon disease and/or blue mold of citrus is provided.
3. A bacteriostatic agent for preventing and treating citrus yellow dragon disease or/and penicilliosis, which is characterized in that: the bacteriostatic agent contains 1-hydroxy-2-piperidinecarboxylic acid, wherein the effective concentration of the 1-hydroxy-2-piperidinecarboxylic acid is more than or equal to 300 mug/mL.
4. A bacteriostatic agent according to claim 3, characterized in that: the effective concentration of the 1-hydroxy-2-piperidinecarboxylic acid is 500-1000 mug/mL.
5. A method for inhibiting yellow dragon disease, which is characterized by comprising the following steps: the method is to inject the bacteriostat of claim 3 into the disease tree through leaf injection.
6. The method of inhibiting yellow dragon disease according to claim 5, wherein: the method comprises the following specific steps: when the citrus leaves are ill, the small holes are punctured by the needle heads on the back surfaces of the diseased leaves, and the mesophyll cells are filled with a bacteriostat through a syringe, wherein the effective concentration of the 1-hydroxy-2-piperidinecarboxylic acid in the bacteriostat is 500-1000 mug/mL.
7. A method for inhibiting the green mold is characterized in that: the method is carried out by immersing the bacteriostat of claim 3 in citrus peel.
8. The method for inhibiting saprolegniasis according to claim 7, wherein: according to the method, after citrus fruits are harvested, small holes with the depth of 1mm are respectively punched on two sides of the fruits by using inoculating needles, 5 mu l of bacteriostat is absorbed and is dripped at the small holes, the bacteria can be absorbed after about 1.5 hours, the periphery of the small holes has obvious inhibition effect on inoculated penicillium, and the effective concentration of 1-hydroxy-2-piperidinecarboxylic acid in the bacteriostat is 500-1000 mu g/mL.
CN202311865947.4A 2023-12-29 2023-12-29 Application of 1-hydroxy-2-piperidinecarboxylic acid in preventing and treating citrus yellow dragon disease and/or green mold Pending CN117859751A (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW201334692A (en) * 2012-01-21 2013-09-01 拜耳智慧財產有限公司 Use of host defense inducers for controlling bacterial harmful organisms in useful plants
CN104650060A (en) * 2014-12-17 2015-05-27 南开大学 Piperidine thiazole derivatives as well as preparation method and use of piperidinethiazole derivatives
CN104823626A (en) * 2015-03-31 2015-08-12 杨正庭 Agricultural ecological technique capable of preventing and controlling liberobacter asiaticum as well as harvesting organic oranges
US20200255851A1 (en) * 2019-01-23 2020-08-13 Spogen Biotech Inc. Compositions for treating citrus disease and promoting yield increase in row crops
US20200367495A1 (en) * 2017-11-15 2020-11-26 Heinrich Heine Universitaet Duesseldorf Method for inducing acquired resistance in a plant

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW201334692A (en) * 2012-01-21 2013-09-01 拜耳智慧財產有限公司 Use of host defense inducers for controlling bacterial harmful organisms in useful plants
CN104650060A (en) * 2014-12-17 2015-05-27 南开大学 Piperidine thiazole derivatives as well as preparation method and use of piperidinethiazole derivatives
CN104823626A (en) * 2015-03-31 2015-08-12 杨正庭 Agricultural ecological technique capable of preventing and controlling liberobacter asiaticum as well as harvesting organic oranges
US20200367495A1 (en) * 2017-11-15 2020-11-26 Heinrich Heine Universitaet Duesseldorf Method for inducing acquired resistance in a plant
US20200255851A1 (en) * 2019-01-23 2020-08-13 Spogen Biotech Inc. Compositions for treating citrus disease and promoting yield increase in row crops

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