Application of acrylamide compound as herbicide

Abstract

The invention relates to the field of agricultural biopesticides, and particularly discloses application of a novel herbicide compound N-(3-(trifluoromethyl) benzyl) acrylamide compound in preparation of a weeding agent. When the N-(3-(trifluoromethyl) benzyl) acrylamide compound and the side chain group substituted analogue thereof are applied to agriculture, the growth of weeds can be effectively inhibited, and the N-(3-(trifluoromethyl) benzyl) acrylamide compound and the side chain group substituted analogue thereof have the characteristics of safety, environment friendliness and high efficiency.

Description

TECHNICAL FIELD

[0001] The present application belongs to the field of agricultural biological pesticides, and relates to a novel herbicide compound N-(3-(trifluoromethyl)benzyl)acrylamide and its application in agriculture (hereinafter referred to as "weed-free spirit"), in particular to a compound with high herbicidal activity and a use method thereof. BACKGROUND

[0002] In modern agricultural production, weeds have always been a key factor hindering the healthy growth and yield improvement of crops. Common intercropping weeds include monocotyledonous weeds such as Digitaria sanguinalis, Setaria viridis and dicotyledonous weeds such as Amaranthus retroflexus, Portulaca oleracea, etc. They compete fiercely with crops in water uptake, nutrient absorption, light utilization and growth space occupation, which not only seriously reduces the output and quality grade of crops, but also can become a carrier for the spread of diseases and pests. Therefore, scientific and effective control of weeds is a core link to ensure the efficiency of agricultural production.

[0003] At present, various means are used for weed control, mainly including mechanical weeding, manual weeding, chemical weeding and biological control, etc. Among them, chemical weeding has become the most widely used weed control method in modern agriculture due to its high efficiency, fast effect and labor and time saving, and has made an irreplaceable contribution to ensuring the yield and income of crops. At present, the types of herbicides widely used in the market mainly include glyphosate, paraquat, 2,4-D, etc. However, in the long-term application practice of existing chemical herbicides, many disadvantages have gradually emerged: some herbicides have poor selectivity and are prone to cause phytotoxicity to crops; some herbicides have a long persistence or slow degradation rate, which is easy to form residues in soil and water, thereby causing environmental pollution problems; and some highly toxic herbicides may be enriched through the food chain, which poses potential hazards to the stability of the ecological system and human health.

[0004] In summary, in view of the defects of existing herbicides, it is of great practical significance to develop a new type of herbicide with higher herbicidal activity, better selectivity and lower toxicity for the sustainable development of agriculture. SUMMARY

[0005] In view of the deficiencies in the prior art, the present application provides an application of N-(3-(trifluoromethyl)benzyl)acrylamide compound (hereinafter referred to as "weed-free spirit") in preparing a weed-killing agent.

[0006] N-(3-(trifluoromethyl)benzyl)acrylamide, chemical formula C 11 H 10 F3NO, molecular weight of 229 g / mol, colorless and odorless crystals. Acrylamide group can be used as Michael acceptor, covalently bind to the thiol (-SH) of plant enzymes (such as cysteine protease, glutathione-S-transferase), interfere with metabolism. Trifluoromethyl (-CF3) can improve the chemical stability and biological activity of the compound. Experiments found that N-(3-(trifluoromethyl)benzyl)acrylamide has a significant inhibitory effect on monocotyledonous and dicotyledonous weeds such as crabgrass, dogtail grass, amaranthus retroflexus and portulaca oleracea, and shows good selectivity and low toxicity.

[0007] Application of N-(3-(trifluoromethyl)benzyl)acrylamide compound in inhibiting weed growth.

[0008] The N-(3-(trifluoromethyl)benzyl)acrylamide compound provided by the application has the following structural formula.

[0009]

[0010] As a preferred embodiment of the application, the weeds include crabgrass, dogtail grass, amaranthus retroflexus, portulaca oleracea and other common weeds in agricultural production.

[0011] As a preferred embodiment of the application, the N-(3-(trifluoromethyl)benzyl)acrylamide compound also includes its side chain group substituted analogs.

[0012] A method for inhibiting weed growth, characterized by applying N-(3-(trifluoromethyl)benzyl)acrylamide and its side chain group substituted analogs to target weeds or their growth sites.

[0013] The application mode includes spraying, soil treatment or seed treatment and the like.

[0014] Up to now, there is no research, report and patent involving the compound as a herbicide.

[0015] The main advantages and positive effects of the application are as follows:

[0016] The application confirms that the N-(3-(trifluoromethyl)benzyl)acrylamide compound can inhibit plant growth, can inhibit the occurrence and growth of weed plant seedling roots through soaking treatment, can inhibit the growth of weed plant seedlings through spraying treatment, can control or prevent the growth of undesirable plants through spraying treatment, and has very high environmental and biological safety, is easy to industrialize, and has the potential to develop into a herbicide. BRIEF DESCRIPTION OF DRAWINGS

[0017] Figure 1Chlorophyll synthesis and growth inhibition of Arabidopsis by chloroacetanilide

[0018] Figure 2 Chloroacetanilide damage to weeds

[0019] Figure 3 Chloroacetanilide induced necrosis of tobacco leaves DETAILED DESCRIPTION

[0020] The preferred embodiments of the present application will be described herein below with reference to the accompanying drawings; it needs to be understood that the following embodiments are given only for the purpose of illustration and are not intended to limit the scope of the present application. Those skilled in the art can make various modifications and replacements to the present application without departing from the spirit and principles of the present application.

[0021] The present application provides a method for controlling or preventing the growth of undesirable plants, comprising applying a herbicidally effective amount of N-(3-(trifluoromethyl)benzyl)acrylamide compound (hereinafter referred to as "chloroacetanilide") or a composition thereof to the plants, parts thereof or the growth site thereof. The application method can include but is not limited to spraying, soil treatment or seed treatment. The following examples are used to illustrate the specific embodiments of the present application, but do not constitute a limitation on the present application.

[0022] Example 1 Detection of chloroacetanilide inhibition of Arabidopsis growth and chlorophyll synthesis

[0023] Take 5.5 mg of the herbicide compound chloroacetanilide of the present application, add 500 μL of DMSO to dissolve, and prepare 10 ml of 2.5 mM stock solution. According to different proportions, dilute the stock solution to 1 μM, 10 μM, 25 μM and 50 μM with 1 / 2MS solid medium. After disinfection, 30 seeds of each type of Arabidopsis wild type were spotted on the surface of the medium, and were incubated under the conditions of temperature 28°C, 16 hours (h) of light and 8 h of darkness per day (d). After 6 days (d), the growth conditions of each test material were observed and recorded. The distance between the two cotyledon tips was measured as the cotyledon length, which represents the judgment of the plant development condition. The comparison of the growth inhibition of chloroacetanilide on Arabidopsis at different concentrations is shown in Table 1. Figure 1 and Table 1.

[0024] Table 1 Detection of chloroacetanilide inhibition of Arabidopsis growth

[0025]

[0026] Figure 1 The results of Table 1 show that chloroacetanilide has obvious inhibitory effect on the development of Arabidopsis, which is manifested as slow plant growth, small leaves and leaf whitening Figure 1 ). This indicates that chloroacetanilide kills plants by inhibiting chlorophyll synthesis.

[0027] Example 2 Test of the killing effect of the compound on weeds

[0028] (1) Reagents:

[0029] The compound was dissolved in 100 μL DMSO, then 0.1‰ emulsifier was added, and the volume was made up to 10 mL with distilled water. The solution was sprayed on the weeds using a watering can.

[0030] (2) Test materials:

[0031] The dicotyledonous plants were chosen to be amaranthus, and the monocotyledonous plants were chosen to be crabgrass and dogtail grass.

[0032] (3) Cultivation of the test plants

[0033] Twelve seeds of each type of test material were selected and evenly sown in a square seedling tray with a diameter of 6 x 6 cm. The bottom soil in the pot was 350 g of soil sieved through a 5 mm sieve, and the top was 50 g of soil sieved through an 8 mm sieve. After the soil was fully watered, the pots were placed in a 25 °C greenhouse test bench in three groups. One group was not treated, one group was sprayed with a solution containing 1% DMSO, and one group was sprayed with a solution containing 1 mM of the compound and 1% DMSO. Then the pots were placed back on the greenhouse test bench.

[0034] (4) Test

[0035] After 7 days, the number of surviving plants was checked. The blank group was used as a control, and the mortality rate of the plants treated with the herbicide was calculated according to the following formula.

[0036] Treatment mortality rate = (total number of test plants - number of surviving plants) / total number of test plants x 100%.

[0037] The killing effect of the compound on the test plants after treatment of the stems and leaves of the potted plants is shown in Table 2 and Figure 2 .

[0038] Table 2 Killing effect of the compound on weeds

[0039]

[0040] The results in Table 2 show that the compound has a significant toxic effect on crabgrass, dogtail grass, amaranthus, and amaranthus, which can cause the death of germinated seedlings, and has good herbicidal activity.

[0041] Example 3 Test of the root growth inhibition effect of the compound on weeds

[0042] With the test material of Digitaria sanguinalis, Amaranthus retroflexus, Portulaca oleracea, compound grass net spirit 22 mg, 1 mL DMSO was dissolved, and distilled water was added to 100 mL to prepare 1 mM mother liquor. According to different proportions, the mother liquor was diluted with distilled water to 100 μM, 250 μM, 500 μM as the experimental group, and 0.5% DMSO as the control group. 5 mL solution was added to the flat dish with filter paper with a diameter of 12 cm.

[0043] Each type of standard consistent test material seed was added to the flat dish, and placed in a temperature of 28°C, dark conditions for cultivation. After the test material seed was exposed, the growth status of each test material was observed and recorded, and the main root length of each test material under different concentration treatment was measured, representing the judgment of germination rate.

[0044] Table 3 Comparison of the main root growth inhibition effect of compound grass net spirit on weeds

[0045]

[0046] As shown in Table 3, compound grass net spirit has obvious inhibitory effect on seed germination rate, and the germination rate of monocotyledonous weed Digitaria sanguinalis under 500 μM compound grass net spirit treatment is 0%, which is significantly lower than that of the control group.

[0047] Example 4: Detection of damage effect of grass net spirit on tobacco in vitro leaf

[0048] Nicotiana benthamiana leaf was used as test material, compound grass net spirit 22 mg was dissolved in 1 mL DMSO, and distilled water was added to 10 mL to prepare 10 mM mother liquor. According to different proportions, the mother liquor was diluted with distilled water to 10 μM, 100 μM, 500 μM, 2.5 mM. A needle was used to slightly prick the edge of the back of the in vitro leaf, and the solution was added to the wound of the leaf. All samples were cultured in a growth chamber at 25°C under white light (200 μmol m -2 s -1 ) for 48 h with a light period of 12 h light and 12 h dark.

[0049] The necrosis condition of tobacco leaf was observed (Figure), and the necrosis area and chlorophyll fluorescence parameter (Fv / Fm) under different concentration treatment were measured. According to the necrosis area of the leaf, it was divided into four grades of A, B, C and D:

[0050] A greater than 40 mm 2 ; B 10 mm 2 to 40 mm 2 ; C 1 mm 2 to 10 mm 2 ; D 0 to 1 mm 2 .

[0051] Table 4 Comparison of the killing effect of compound CQ on tobacco leaves

[0052]

[0053] From Table 4 and Figure 3 It can be seen that CQ can cause the necrosis of tobacco leaves and affect the light energy conversion efficiency of the reaction center of photosystem II. It is shown that CQ has the ability to inhibit the photosynthesis of plants.

[0054] The contents not described in detail in the specification belong to the prior art known to those skilled in the art.

[0055] Finally, it should be noted that: the above only for the preferred examples of the present application, and not for limiting the present application, although the foregoing examples of the present application are described in detail, for those skilled in the art, it still can be modified, or part of the technical features of the equivalent replacement of the technical solutions recorded in the foregoing embodiments. Any modification, equivalent replacement, improvement, etc. within the spirit and principles of the present application shall be included in the protection scope of the present application.

Claims

1. Application of N-(3-(trifluoromethyl)benzyl)acrylamide compounds in the preparation of herbicides.

2. Application of N-(3-(trifluoromethyl)benzyl)acrylamide compounds in suppressing weed growth.

3. The application according to claim 1 or 2, characterized in that, The weeds include crabgrass, foxtail grass, amaranth, purslane, and other common weeds in agricultural production.

4. The application according to claim 1 or 2, characterized in that, The N-(3-(trifluoromethyl)benzyl)acrylamide compounds also include analogs with substituted side chain groups.

5. A method for suppressing weed growth, characterized in that, Apply N-(3-(trifluoromethyl)benzyl)acrylamide and its side-chain group-substituted analogues to the target weeds or their growth sites.

6. The method as described in claim 5, characterized in that, The application methods include spraying, soil treatment, or seed treatment.

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