New weeding application of natural phosphonic acid compound Argolaaphos A

Abstract

The invention belongs to the technical field of pesticides, and particularly relates to novel weeding application of a natural phosphonic acid compound Argolaaphos A. The structural formula of the natural phosphonic acid compound Argolaaphos A is # imgabs0. The research finds that the natural phosphonic acid compound Argolaaphos A has a remarkable weeding effect on cruciferous plant arabidopsis thaliana, and can inhibit the growth of leaves of the arabidopsis thaliana, reduce the root length of the arabidopsis thaliana and reduce the total fresh weight of the arabidopsis thaliana. Therefore, the natural phosphonic acid compound Argolaaphos A can be used as a herbicide or prepared into the herbicide.

Description

Technical Field

[0001] The invention belongs to the technical field of pesticides, and in particular relates to a new weeding application of a natural phosphonic acid compound ArgolaphosA. Background Art

[0002] Phosphonic acid compounds are a class of compounds that contain carbon-phosphorus bonds in their chemical structures. These compounds are widely found in nature and have a variety of biological activities. They are widely used in medicine (such as antibiotics, antimalarial drugs), agriculture (such as fertilizers and herbicides), synthetic chemistry (such as catalysts), industry (such as metal chelators, antifouling agents, water treatment agents) and cosmetics. As structural analogs of phosphate and carboxylic acid compounds, phosphonic acid small molecules can compete for the active sites of enzymes in biochemical reactions, thereby blocking specific biochemical reactions and achieving the effect of inhibiting or killing target organisms. The CP bonds in these compounds also give them extremely high structural stability.

[0003] By 2024, more than 30 phosphonic acid small molecule natural products with significant pharmacological activity have been isolated from nature. For example, Monourol (chemical name Fosfomycin, Chinese name Fosfomycin) used to treat urinary tract infections inhibits the activity of UDP-nitrogen-acetylglucosamine-3-oxy-enolpyruvate transferase by simulating the structure of phosphoenolpyruvate, thereby effectively inhibiting bacterial growth. In addition, the pharmacophore of Bialaphos (PPT), glufosinate, as a structural analogue of glutamate, can competitively inhibit the activity of glutamine synthetase and exhibit broad-spectrum antibacterial and antifungal activity, so it is widely used in the research and development and production of antibiotics. Others such as FR-900098 and Fosmidomycin show strong antimalarial activity, Rhizocticin has good antifungal ability, and K-26 has the potential to treat hypertension. These findings show the diversity and importance of phosphonic acid small molecule natural products in terms of biological activity, which is of great significance to human production and life.

[0004]

Harnessing phosphonate antibiotics argolaphos biosynthesis enables a synthetic biology-based green synthesis of glyphosate. Nature Communications. DOI: 10.1038 / s41467-022-29188-6.

[0005] Common active ingredients of herbicides currently include glyphosate, glufosinate, chlorpyrifos, chlorpheniramine, pyraclostrobin, etc. However, long-term use of the same herbicides leads to weed resistance and brings a series of environmental and health problems. In addition, the abuse and improper use of herbicides may lead to soil and water pollution and have a negative impact on non-target plants and biodiversity. Therefore, it is urgent to develop new herbicides to provide more efficient and safer weed control methods, help farmers protect crops from weeds, improve yield and quality, reduce resistance, and thus promote the sustainable development of agriculture and horticulture.

[0006] AmPn is an α-aminophosphonate analog of glycine and a key component in the synthesis of the neuroactive agent EAB-318 and the herbicide glyphosate. So, do compounds containing AmPn have herbicidal activity? [Arthur Mucha, Roman Tyka, Pawel Kafarski. Preparation, crystal and molecular structure, and evaluation of plant growth regulation activity of guanidinoalkanephosphinates and phosphonates. Heteroatom Chemistry. DOI: 10.1002 / hc.520060508.] discloses a compound P-[(alpha-guanidino)methyl]phosphonic acid synthesized from AmPn and guanidine. The herbicidal activity test results show that the compound has no inhibitory activity against Lepidium sativum of the Cruciferae family, indicating that whether the compound contains AmPn or not is not necessarily related to its herbicidal activity.

[0007] The present invention discovered the herbicidal activity of the compound Argolaphos A for the first time, and mainly selected Arabidopsis thaliana of the Cruciferae family as the activity test object. By monitoring the inhibitory effect of Argolaphos A on Arabidopsis thaliana, its potential as a new herbicide was evaluated. Summary of the invention

[0008] The object of the present invention is to provide a new herbicidal use of the natural phosphonic acid compound Argolaphos A.

[0009] To achieve the above object, the present invention adopts the following technical solutions: The application of the natural phosphonic acid compound Argolaphos A as a herbicide, the structural formula of the natural phosphonic acid compound Argolaphos A is as follows: The herbicide acts on plants of the cruciferous family; The cruciferous plant is Arabidopsis thaliana.

[0010] The application of the natural phosphonic acid compound Argolaphos A in the preparation of herbicides, wherein the structural formula of the natural phosphonic acid compound Argolaphos A is as follows: The herbicide acts on plants of the cruciferous family; The cruciferous plant is Arabidopsis thaliana.

[0011] The application of the natural phosphonic acid compound Argolaphos A in inhibiting the growth of cruciferous plants, the structural formula of the natural phosphonic acid compound Argolaphos A is as follows: The inhibiting the growth of cruciferous plants includes inhibiting the growth of cruciferous plant leaves, reducing the root length of cruciferous plants, and reducing the total fresh weight of cruciferous plants; The cruciferous plant is Arabidopsis thaliana.

[0012] The significant advantages of the present invention are: The present invention first discovered the herbicidal activity of the natural phosphonic acid compound Argolaphos A, selected the cruciferous plant Arabidopsis thaliana as the activity test object, and monitored the inhibitory effect of Argolaphos A on Arabidopsis thaliana. The results showed that Argolaphos A had a more significant inhibitory effect on the leaf growth of Arabidopsis than glufosinate, a more significant inhibitory effect on the total fresh weight of Arabidopsis than glyphosate and glufosinate, and a more significant inhibitory effect on the root length of Arabidopsis than glufosinate and equivalent to glyphosate. This indicates that the natural phosphonic acid compound Argolaphos A has the potential to be used as a new herbicide. BRIEF DESCRIPTION OF THE DRAWINGS

[0013] Figure 1 :Schematic diagram of the preparation process of Argolaphos A.

[0014] Figure 2 : The structural formula of Argolaphos A.

[0015] Figure 3 : Argolaphos A 1 H-NMR spectrum.

[0016] Figure 4 : Argolaphos A 13 C-NMR spectrum.

[0017] Figure 5 : Herbicidal activity of Argolaphos A against Arabidopsis thaliana. DETAILED DESCRIPTION

[0018] In order to make the contents of the present invention easier to understand, the technical solution of the present invention is further described below in conjunction with specific implementation methods, but the present invention is not limited thereto.

[0019] Embodiment 1: The preparation method and structural identification results of the natural phosphonic acid compound Argolaphos A have been disclosed in [Harnessing phosphonate antibiotics argolaphos biosynthesis enables a synthetic biology-based green synthesis of glyphosate. Nature Communications. DOI: 10.1038 / s41467-022-29188-6.].

[0020] Figure 1 Schematic diagram of the preparation process of Argolaphos A. Figure 2 is the structural formula of Argolaphos A. Figure 3 For Argolaphos A 1 H-NMR spectrum (400 MHz, D2O). Figure 4 For Argolaphos A 13 C-NMR spectrum (100 MHz, D2O).

[0021] Embodiment 2: Arabidopsis seed cleaning and germination culture: In the clean bench, take a small amount of Arabidopsis seeds into a sterilized 2ml centrifuge tube, wash with anhydrous ethanol for 5min, then wash with 75% ethanol solution for 5min, and then wash with sterile water for 6-7 times for standby use. Prepare MS solid culture medium, sterilize, pour into a square culture dish, the culture medium volume is about 15ml / plate, after the culture medium solidifies, take 1ml of 1% agarose aqueous solution and add it to the washed Arabidopsis seeds, use a 1ml pipette to suck out the seeds, and dot on the MS solid culture medium plate, seal it and place it in a 4℃ refrigerator for vernalization for 2-3 days, then culture it at 23℃, 16h light / 8h dark conditions for 3 days, and observe the seed germination.

[0022] Prepare 50 ml of MS solid culture medium, sterilize, cool to an appropriate temperature in a clean bench, add 500 μl of sterilized glyphosate aqueous solution to prepare a culture medium mixed liquid containing 0.05 mM glyphosate; prepare 50 ml of MS solid culture medium, sterilize, cool to an appropriate temperature in a clean bench, add 500 μl of sterilized glufosinate aqueous solution to prepare a culture medium mixed liquid containing 0.05 mM glufosinate; prepare 50 ml of MS solid culture medium, sterilize, cool to an appropriate temperature in a clean bench, add 500 μl of sterilized Argolaphos A aqueous solution to prepare a culture medium mixed liquid containing 0.05 mM Argolaphos A; prepare 50 ml of MS solid culture medium, sterilize, cool to an appropriate temperature in a clean bench, add 500 μl of sterilized sterile water to obtain a blank control culture medium liquid (Note: Add glyphosate, glufosinate, Argolaphos A. The temperature of the culture medium is maintained at 45-50°C, and the sample is shaken slowly to ensure that the sample and the culture medium are fully mixed to prevent the generation of bubbles and uneven growth of the seedlings in the later stage. Pour 15 ml of the mixed liquid on each plate. After solidification, the germinated Arabidopsis seedlings are gently picked up with a sterile pipette tip and transferred to each culture medium. After sealing, they are cultured at 23°C and 16h light / 8h dark conditions for 7 days. After that, their growth is observed. Finally, tweezers are used to gently pull the Arabidopsis so that the plants are basically not sticky to the agar. The root length is immediately measured. After that, the Arabidopsis is placed on a paper towel and gently pressed to ensure that the root system does not contain agar and then its fresh weight is measured.

[0023] Results and Analysis: In the experiment of inhibiting the growth of Arabidopsis, water was used as the blank control group, and the experimental groups were 0.05mM Argolaphos A, glyphosate and glufosinate. After the Arabidopsis seedlings grew for 7 days, the experimental groups and the blank control group were observed, and it was found that the growth of the roots and leaves of the Arabidopsis seedlings in the three experimental groups was significantly inhibited compared with the blank control group. Figure 5 a is a phenotype diagram of Arabidopsis seedlings after 7 days of growth. Argolaphos A has a weaker inhibitory activity on Arabidopsis leaf growth than glufosinate, but a more significant inhibitory activity than glufosinate. Figure 5 b is a bar graph of the total fresh weight of Arabidopsis seedlings in four groups. 22 plants in each group were counted and the average value was taken. Argolaphos A, glyphosate and glufosinate all significantly reduced the total fresh weight of Arabidopsis seedlings. The inhibitory effect of ArgolaphosA on the total fresh weight of Arabidopsis was more significant than that of glyphosate and glufosinate. Figure 5 c is a graph of the root length of Arabidopsis seedlings. Argolaphos A has a more significant inhibitory effect on the root length of Arabidopsis seedlings than glufosinate, and its inhibitory effect is comparable to that of glyphosate on the root length of Arabidopsis seedlings.

[0024] The above description is only a preferred embodiment of the present invention. All equivalent changes and modifications made according to the scope of the patent application of the present invention should fall within the scope of the present invention.

Claims

1. The use of the natural phosphonic acid compound Argolaphos A as a herbicide, characterized in that: The structural formula of the natural phosphonic acid compound Argolaphos A is as follows:

2. The use according to claim 1, characterized in that: The herbicide acts on cruciferous plants.

3. The use according to claim 2, characterized in that: The cruciferous plant is Arabidopsis thaliana.

4. Application of the natural phosphonic acid compound Argolaphos A in the preparation of herbicides, characterized in that: The structural formula of the natural phosphonic acid compound Argolaphos A is as follows:

5. The use according to claim 4, characterized in that: The herbicide acts on cruciferous plants.

6. The use according to claim 5, characterized in that: The cruciferous plant is Arabidopsis thaliana.

7. Use of the natural phosphonic acid compound Argolaphos A in inhibiting the growth of cruciferous plants, characterized in that: The structural formula of the natural phosphonic acid compound Argolaphos A is as follows:

8. The use according to claim 7, characterized in that: The inhibiting the growth of cruciferous plants includes inhibiting the growth of cruciferous plant leaves, reducing the root length of cruciferous plants, and reducing the total fresh weight of cruciferous plants.

9. The use according to claim 7, characterized in that: The cruciferous plant is Arabidopsis thaliana.

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