KR101294783B1 - Herbicidal composition against Sciyos angulatus L. comprising plumbagin derived from Plumbago auriculata - Google Patents

Abstract

The present invention is Plumbago ( Aurikulata) Auriculata ) relates to a herbicide composition containing a plumumbag (plumbagin) derived as an active ingredient, specifically, to determine whether the natural product-derived naphthoquinone compound is effective herbicide, derived from the worm family Plumbago aurikulata of the present invention Since the natural naphthoquinone compound plumbagin has KAPAS inhibitory activity and inhibits KAPAS important for plant growth, it shows excellent control effect against Sciyos angulatus L. It is available.

Description

Composition for control of thorns containing plumbagin as active ingredient {Herbicidal composition against Sciyos angulatus L. comprising plumbagin derived from Plumbago auriculata}

The present invention relates to a composition for controlling prickly pear containing plumpgin (plumbagin) as an active ingredient.

Sciyos angulatus L. is a naturalized plant native to North America that is a weed that is seriously destroying ecosystems by collectively occurring in riversides, roadsides, railroads, agricultural lands, and surrounding areas. The rule states that “Ecosystem is a wild plant”. Spiny gourds grow vigorously, produce a lot of seeds, grow in colonies, and cover herbaceous plants as well as trees, inhibiting photosynthesis and killing them, destroying existing vegetation by destroying and polluting soil moisture and nitrogen. In addition, the thorns on the seed epidermis cause direct skin damage, such as causing dermatosis. In fact, barley is currently distributed all over the country and gradually spread the distribution area causing serious damage is urgently required to develop a control technology for its control (see Fig. 1).

Known methods for removing barbed gourds are to cut or pluck young plants, which require a great deal of labor. Some prickly pears can be controlled by using non-selective organic synthetic herbicides such as paraquat or glyphosate, but the main source and colonies of prickly pear are mainly riversides, roadsides, or people's activities. Because of the surroundings, the control using the actual organic synthetic herbicides is practically very limited.

  Furthermore, due to the emergence of resistant weeds and the potential impacts on ecosystems and environmental pollution as a result of the continuous use of organic synthetic herbicides, and as interest in environmentally friendly agriculture has increased as income and quality of life have been emphasized Since regulations are being tightened around the world in order to reduce the use of synthetic pesticides, it is becoming more difficult to control the visible poultry, which occurs mainly in living areas, using conventional organic synthetic herbicides.

Therefore, there is an urgent need for a technique for environmentally controlling spiny gourd using natural products or biochemicals, which have low shrinkage toxicity and are easily decomposed under natural conditions.

Eco-friendly herbicides are active substances derived from natural products originating from soil microorganisms and plants, such as the genus Streptomyces .

In foreign studies on natural herbicides derived from soil microorganisms and plants, Colletorichum gloeosporioides , Phytophthora Raise (Pseudomonas palmivora), Pseudomonas geulradi gladioli ) as a herbicidal herbicide for Zygomycetes japonica, Ivy and ivy, and for the control of herbicides. In the case of research on herbicidal active substances in plants, anthraquinone, naphtha, Recent studies have reported that natural compounds based on naphthoquinone or benzoquinone inhibit hydroxyphenylpyruvate dioxygenase (HPPD).

Efforts to discover herbicide-active substances derived from natural products continue, but most of the microbial herbicides or plant-derived active substances herbicides, which are currently being researched and developed, are mostly targeted to weeds in farmland. There are no research cases or technological developments conducted on barley that are in question all over the world.

In the case of domestic research on herbicides derived from soil microorganisms or plants, there have been cases of 'diclover' which selectively acts on soybean weeds from BWC98-105 strains isolated / identified from clover parasites. Genus Penicillium , Phytophthora , Exserohilum monoceras), call rekto tree Com Graeme Nicolas the weed control is attempted using a plant pathogen, such as (Colletotrichum graminicola), and, as the active substance herbicide of a plant origin is Japanese pepper, sapju, baby swim pasqueflower including domestic such as native plants or elecampane There have been attempts to search for natural herbicidally active substances from medicinal plants or essential oils of Palmarosa, but there have been no studies conducted on the control of barley gourds.

If the herbicides developed and utilized to date are classified in detail, they can be divided into 17 kinds according to the type of physiological action. Of these, herbicides whose functionality is enhanced by light occupy a large proportion, and these mainly act on enzymes. For example, glutamines synthetase, acetolactate synthase, which acts on ALA synthase and protoporphyrinogen oxidase, which are involved in photosynthetic pigment synthesis, or is involved in amino acid biosynthesis. ) And beta-tubulin, which act on EPSP synthase, on acetyl-CoA carboxylase, an enzyme involved in lipid biosynthesis, or on cell division. It is known to act on. As such, herbicides have different mechanisms of action depending on the enzyme to be acted upon, and the herbicides have different types of plants.

Hydroxyphenylpyruvate dioxygenase (HPPD), one of the action points showing herbicidal activity, is an enzyme involved in carotenoid biosynthesis. When the enzyme's function is inhibited, its synthesis is inhibited and the leaves become white. Plant growth is inhibited. Since it has been reported that benzoquinone, natural naphthoquinone and anthraquinone can be used as herbicides by inhibiting the function of HPPD (Phytochemistry 59, 2002), substance components showing herbicidal activity through HPPD inhibition mechanism have been reported. It is becoming.

Recently, 7-keto-8-aminopelargonic acid synthase (KAPAS) has emerged as a target of herbicide (Peticide Biochemistry and physciology 97, 2010).

KAPAS is an enzyme that plays an important role in the early stages of biotin biosynthesis. When this enzyme's function is inhibited, the leaves dry and inhibit plant growth and do not germinate. Accordingly, substances that inhibit the function of KAPAS show excellent effects as herbicides.

On the other hand, looking at the relationship between the inhibition of HPPD and KAPAS activity by the compound, although the degree of activity inhibition of the two enzymes according to the compound may be consistent, there is a case that there is no correlation between the two enzyme inhibitory activity. For example, anthraquinone, emodine, has little HPPD inhibitory activity, and KAPAS inhibitory activity is also very low. In the case of 1,2-naphthoquinone, HPPD inhibition is moderate but KAPAS inhibition is very good. However, Lapacol and 2-hydroxy-naphthoquinone do not have HPPD inhibitory activity but KAPAS inhibitory activity is excellent. Therefore, HPPD and KAPAS do not always show the same inhibitory activity by a specific compound, and therefore, it cannot be predicted that a certain compound has an inhibitory activity against the two enzymes at the same time.

The present inventors, while trying to find an environmentally friendly natural product-derived herbicide, the natural naphthoquinone compound plumbagin derived from the worm family Plumbago auriculata acts on biotin biosynthesis and is important for plant growth. The present invention was completed by suppressing the KAPAS action that plays a role and controlling spiny gourd.

An object of the present invention is to provide a herbicide composition containing plumumbag as an active ingredient.

In order to solve the above problems, the present invention provides a composition for the control of visible foil containing plum pumgin (plumbagin) as an active ingredient.

Natural naphthoquinone compound plumbagin derived from the worm family Plumbago auriculata of the present invention has an excellent inhibitory activity against KAPAS involved in plant growth, and this is Sciyos angulatus L.) shows excellent control effect.

1 is a photograph showing a barbed bakbak into Korea.
2 is a graph showing KAPAS inhibition by plumbagin.
Figure 3 is a view showing the effect of control of plumbing in plum greenhouse in greenhouse conditions:
CK: control group;
Plumbagin: plumbagin treatment group; And
Days after treatment (DAT): Days after treatment.
Figure 4 is a view showing the effect of visible foil control of plumbagin in packaging conditions.

Hereinafter, the present invention will be described in detail.

The present invention contains plumumbagin (plumbagin) as an active ingredient, and provides a herbicide composition of Sciyos angulatus L.

Plum is the plum bagin Bago Auriga other Kula (Plumbago auriculata ) may be derived from, but is not limited thereto.

The plumbagin has a structural formula represented by the following formula (1).

The plumbagin inhibits 7-keto-8-aminopelargonic acid synthase (KAPAS) activity.

The plumbagin may be one to be treated at a concentration of 500 to 2,500 µg / ml, and specifically, the plumbagin may be one to be treated at a concentration of 1,000 to 2,000 µg / ml.

The inventors have studied Arabidopsis for 528 plant-derived natural materials deposited with the Chemica Bank of Korea. thaliana ) AtKAPAS protein was used to evaluate the inhibitory effect on 7-keto-8-aminopelargonic acid synthase (KAPAS). It was a natural naphthoquinone. Plumbagin was found to have a potent KAPAS inhibitory effect. Plumbagin was confirmed to have an inhibitory effect on KAPAS concentration-dependently, IC ₅₀ was calculated to 2.1 μM (see Fig. 2).

In order to prepare the plant material, the seeds of prickly seed used in the experiment were sown and grown by bottom irrigation in a greenhouse condition of 28 ± 5 ° C. (light / dark = 14 hours / 10 hours). When the final treatment concentration of plumbagin (plumbagin; 5-hydroxy-2-methyl-1,4-naphthoquinone) (Sigma-Aldrich) was treated to a concentration of 1,000 µg / ml to the prepared spiny foil, The external symptoms were very fast-acting and showed 95% control effect after 1 day of treatment, and completely controlled (100%) after 4 days (see FIG. 3).

Plumbagin confirmed the control effect of the spiny foil The activity of the packaging was confirmed. As a result, the external symptoms appeared within a few hours of treatment, which was very fast. The control effects at 1,000 and 2,000 ㎍ / ml concentrations were 100% after 5 days, respectively. The effects were confirmed to be 100% complete, respectively (see Table 2 and Figure 4).

Therefore, it was confirmed that the natural naphthoquinone compound plumbagin has an excellent inhibitory activity against KAPAS involved in plant growth, and when treated with spiny gourd, it has an excellent control effect through the mechanism of inhibiting KAPAS. Since it is confirmed that, the plumbagin can be used as an active ingredient of the herbicide composition for thorn gourd which is specifically inhibited growth through KAPAS inhibition.

In addition, the present invention provides a spiny herbicide method comprising the step of treating the spiny herbicide composition containing plumbagin as an active ingredient to spiny gourd, its seeds or its habitat.

The plumbagin inhibits KAPAS activity.

The plumbagin may be one to be treated at a concentration of 500 to 2,500 µg / ml, and specifically, the plumbagin may be one to be treated at a concentration of 1000 to 2,000 µg / ml.

The herbicide composition may be one that can be used by irrigation to plants, spraying or spraying seeds on the plants in a liquid state, or coating on the seeds, but is not limited thereto.

The herbicide composition may be prepared according to a method known to those skilled in the art, the method of application is usually a method commonly performed, that is, spraying (for example, spraying, misting, atomizing, powder spraying, granulation spraying, sleeping, always Etc.), soil application (e.g. mixing, irrigation, etc.), surface use (e.g., coating, smearing, coating, etc.), dipping, poisoning, and smoking. The amount to be used can be appropriately determined according to the body type, the damage situation, the application method, and the application place.

In the case of the immersion method, the herbicide composition may be poured into the soil around the plant or the seeds may be immersed in the herbicide composition, and when sprayed, the spray may be applied to the plant by techniques well known in the art. It is not limited to this.

Hereinafter, the present invention will be described in detail with reference to examples.

However, the following examples are illustrative of the present invention in detail, and the present invention is not limited to the examples.

 Example 1 Preparation of Plumumbag Compound

Plumbago auriculata : Plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone) isolated from Plumbaginaceae It was purchased from Sigma-Aldrich (Formula 1). The commercially available purity of plumbagin was evaluated at 90% or higher by HPLC. It was further purified by HPLC prior to the experiment.

< Example  2> substrate synthesis and KAPAS  analysis

KAPAS activity was measured by a microplate spectrophotometer (Benchmark Plus, Bio-rad, USA) with a thermostat adjusted to 30 ° C. according to the method described in SP Webster et al., Biochemistry 39 (2000) 516-528. Was confirmed by observing the increase in NADH absorption at 340 nm. Representative analytical methods include 20 mM potassium phosphate (pH 7.5), 1 mM a-ketoglutarate, 0.25 mM thiamine pyrophosphate, 1 mM NAD in 200 μl total volume. ⁺ , 3 mM MgCl ₂ , 0.1 unit a-ketoglutarate dehydrogenase, and 2-10 μg KAPAS were added, L-alanine and pimeloyl- CoA (pimeloyl-CoA) was added at the required final concentration. Pimeloyl-CoA is described in O. Ploux, A. Marquet, Biochem. It was synthesized according to the method described in J. 283 (1992) 327-331. Prior to analysis, enzyme samples were dialyzed against 20 mM potassium phosphate (pH 7.5) containing 100 μM PLP at 4 ° C. for 2 hours. In all assays the KAPAS concentration was 10 μΜ in 20 mM potassium phosphate (pH 7.5) and the concentrations of plumbagin were 0.5, 1, 2, 4, 8 and 16 μΜ. Reference cuvettes included all other compounds except plumbagin.

Plumbagin, a natural naphthoquinone, was found to have the strongest inhibitory effect on KAPAS in a concentration-dependent manner, with an IC ₅₀ of 2.1 μM (FIG. 2).

< Example  3> Preparation of plant material

The barley seeds used in the experiment were screened in October 2010, and the seeds which were grown in the vicinity of Kangwon National University Chuncheon-si pavement were selected and used for the seeds stored at low temperature in 4 ℃ refrigerator. One end of the thick, oval seed was used by cutting a portion with a knife. After filling the 38.5cm ² polystyrene cup with horticulture soil (fuongindustrial company), sowing seed seeds and bottom watering in greenhouse conditions of 28 ± 5 ℃ (light / dark = 14 hours / 10 hours) It was grown.

Example 4 Confirmation of Spiny Bacteria Control Effect in Greenhouse Conditions of Plumbagin

The final treated concentration of plumpgin (plumbagin; 5-hydroxy-2-methyl-1,4-naphthoquinone) ( Sigma-Aldrich ) on the prickly gourd prepared in <Example 3> was weighed to have a concentration of 1,000 μg / ml and acetone. The solution was dissolved in 1 ml, diluted with a pharmaceutical preparation solution (50% acetone, 0.1% Tween-20), and sprayed at 10 ml / pot. After the drug treatment, the drug solution was completely dried in the hood, and then transferred to the same greenhouse condition and managed visually based on the external symptoms 1 and 4 days after the drug treatment. The results of the crown observation ranged from 0 to 100, with 0 indicating no control effect and 100 indicating complete death.

As a result, when plumbagin was treated to spiny gourd, the external symptoms were developed within 2 hours of drug treatment, and it was very fast. It showed 95% control effect after 1 day of treatment, and then completely controlled (100 days). %) (Table 1 and Figure 3).

compound

Treatment concentration
(占 퐂 / ml) Control effect 1 DAT ^* 4 DAT Plumbagin 1,000 95 100

^* Days after treatment (DAT): The number of days after treatment

< Example 5> Confirmation of the control effect of the visible foil under the packaging conditions of plumbagin

In <Example 4> Plumbagin confirmed the control effect of thorns The activity was confirmed in the packaging conditions. The field test was conducted in September 2011 at the Namhan Riverside, 31-15, Andeok-ri, Gaegun-myeon, Yangpyeong-gun, Gyeonggi-do, Korea. ~ 15 blades in length was more than 2-3m. Plumbagin was diluted to a concentration of 2,000 and 1,000 μg / ml in 50% acetone solution containing 0.1% Tween-20 and treated 300 ml per compartment. The experiment was three replicates of 1 m ² land size. Plumbazine was assessed by visual rating scale of 0-100 on days 5, 8 and 14 after 1,000 and 2,000 μg / ml treatment.

As a result, within 2 hours of treatment with plumbagin, the spiny gourd dried or disappeared. After 5 days, the control effects at 1,000 and 2,000 μg / ml treatment concentrations were 100%, respectively. After 8 days of treatment, the control effects at the same concentrations were 100%, respectively. (Table 2 and Fig. 4) . The residual activity lasted for 2 weeks without any regeneration field. As described above, plumbagin has been shown to completely control within the concentration range of the treatment of thorny weed designated as environmental weed for environmental conditions, even in weather conditions such as rainfall or temperature changes, or pavement conditions that are easily decomposed by light.

compound
Treatment concentration
(占 퐂 / ml) Control effect (%) 5 DAT ^* 8 DAT Plumbagin
1,000 100 100 2,000 100 100

Claims (11)

Visible containing plume bagin (plumbagin) as an active ingredient foil (Sciyos angulatus L. ) Herbicide composition for control.
The method of claim 1, wherein the plume is bagin plume Bago Oh we Kula other (Plumbago auriculata ) derived from the herbicide composition for control of thorn foil.
According to claim 1, The plumbagin is a herbicide composition for the control of thorn foil characterized in that the formula (1).

According to claim 1, The plumbagin is a herbicide composition for the control of barbed foil, characterized in that to inhibit the 7-keto-8-aminopelargonic acid synthase (KAPAS) activity.
The method of claim 1, wherein the plumbagin is a herbicide composition for the control of barbed foil, characterized in that the treatment at a concentration of 500 to 2,500 ㎍ / ㎖.
The method of claim 1, wherein the plumbagin is a herbicide composition for the control of spiny foil, characterized in that the treatment at a concentration of 1,000 to 2,000 ㎍ / ㎖.
A spiny herbicide method comprising the step of treating the spiny herbicide herbicide composition containing plumbagin as an active ingredient to spiny gourd, its seeds or its habitat.
8. The method of claim 7, wherein the plumbagin inhibits KAPAS activity.
8. The method of claim 7, wherein the plumbagin is treated at a concentration of 500 to 2,500 μg / ml.
8. The method of claim 7, wherein the plumbagin is treated at a concentration of 1000 to 2,000 ㎍ / ㎖.
8. The method of claim 7, wherein the herbicide composition for controlling prickly pear is irrigated, sprayed or coated on seeds in crops, or irrigated with plants.

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