KR20130063708A - Herbicidal composition against sciyos angulatus l. comprising juglone - Google Patents

Abstract

PURPOSE: Juglone is provided to suppress the function of KAPAS(7-keto-8-aminopelargonic acid synthase) which is related to a biotin biosynthesis pathway of microorganisms and plants, significantly control Sicyos angulatus L., and be used as an active ingredient of a safe natural herbicide. CONSTITUTION: A herbicidal composition for controlling Sicyos angulatus L. contains juglone of chemical formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient. Juglone is derived from a black walnut and suppresses KAPAS activity. A method for controlling Sicyos angulatus L. comprises a step of treating Sicyos angulatus L. a seed thereof, or a habitat thereof with the herbicidal composition. The herbicidal composition is used by dipping, spraying or coating.

Description

Composition for control of thorns containing juglon as an active ingredient {Herbicidal composition against Sciyos angulatus L. comprising Juglone}

The invention visible foil containing primary geulron (Juglone) or a pharmaceutically acceptable salt thereof as an active ingredient (Sciyos angulatus L.) It relates to a composition for controlling.

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 sources and colonies of prickly pear are mainly riversides, roadsides, or people's living quarters. Because of this, the control using the actual organic synthetic herbicide 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 technology that controls environmentally friendly spines by using natural products or biochemicals that are low in toxicity and easy to decompose 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 currently being researched and developed are targeted to weeds occurring 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.

Therefore, the present inventors are trying to find an environmentally friendly natural product-derived herbicide, the natural naphthoquinone compound juglone derived from the walnut (Juglandaceae family) black walnut (microorganism) is a biotin biosynthetic pathway of microorganisms and plants The present invention was completed by confirming that it is possible to control spinach by inhibiting KAPAS (7-keto-8-aminopelargonic acid synthase), which plays a major role in plant growth.

The invention has the main purpose geulron (Juglone) or visible foil containing a pharmaceutically acceptable salt thereof as an active ingredient (Sciyos angulatus L. ) To provide a herbicide composition for control.

In order to solve the above object, the present invention (Sciyos visible foil containing primary geulron (Juglone) or a pharmaceutically acceptable salt thereof represented by the following formula 1 as an active ingredient angulatus L. ) Provides herbicide compositions for controlling:

[Formula 1]

.

.

In addition, the present invention provides a method of weeding thorns comprising the step of treating the composition of the present invention in thorns, its seeds or its habitat.

Juglone (Juglone) according to the present invention is involved in biotin biosynthetic pathways of microorganisms and plants, inhibits the action of 7-keto-8-aminopelargonic acid synthase (KAPAS), which plays a major role in plant growth, and severely damages all areas of Korea. Since it exhibits significant herbicidal activity against the thorns causing, it can be usefully used as an active ingredient of a safe natural herbicide of the human body.

1 is a graph showing the inhibition of 7-keto-8-aminopelargonic acid synthase (KAPAS) by juglone.
Figure 2 is a view showing the effect of controlling the visible foil of juglon in greenhouse conditions:
CK: control group;
Juglone: Juglon treated group; And
Days after treatment (DAT): Days after treatment.
Figure 3 is a view showing the effect of controlling the visible foil of juglon in the packaging conditions.

Hereinafter, the present invention will be described in detail.

The present invention (Sciyos visible foil containing primary geulron (Juglone) or a pharmaceutically acceptable salt thereof represented by the following formula 1 as an active ingredient angulatus L. ) Provides herbicide compositions for controlling:

[Formula 1]

.

.

The juglon is preferably derived from black walnut, but is not limited thereto.

The juglon preferably inhibits KAPAS (7-keto-8-aminopelargonic acid synthase) activity, but is not limited thereto.

The juglon is preferably treated at a concentration of 500 to 2,500 μg / ml, and more preferably at a concentration of 1,000 to 2,000 μg / ml, but is not limited thereto.

Juglon (5-hydroxynaphthoquinone) represented by the formula (1) of the present invention can be used in the form of a pharmaceutically acceptable salt thereof, a pharmaceutically acceptable alkali addition salt is useful as a salt. The expression pharmaceutically acceptable salt is a concentration that has a relatively nontoxic and harmless effect on the subject to be treated, and that any side effects due to the salt do not degrade the beneficial effect of the base compound of formula (1). Or inorganic addition salts. These salts include alkali metal salts (sodium salts, potassium salts, and the like), alkaline earth metal salts (calcium salts, magnesium salts, and the like) and the like. For example, aluminum, arginine, benzatin, calcium, choline, diethylamine, diolamine, glycine, lysine, magnesium, meglumine, olamine, potassium, sodium, tromethamine, zinc salt, and the like can be included. .

In addition, the juglon represented by the formula (1) of the present invention includes not only pharmaceutically acceptable salts, but also all salts, isomers, hydrates, and solvates that can be prepared by conventional methods.

The addition salt according to the present invention can be prepared by a conventional method, for example, by dissolving the compound of Formula 1 in a water miscible organic solvent, such as acetone, methanol, ethanol, or acetonitrile, and adding an excess of base to precipitate Or crystallized. The solvent can then be evaporated and dried in this mixture to yield an addition salt, or the precipitated salt can be prepared by suction filtration.

In a specific embodiment of the present invention, the inventors of the Arabidopsis Arabidopsis for 528 plant-derived natural substances deposited in the Chemcial Bank of Korea Research Institute of Chemical Technology to confirm KAPAS inhibitory activity thaliana ) AtKAPAS protein was used to confirm the inhibitory effect on KAPAS. As a result, it was confirmed that juglon, a natural naphthoquinone, had a strong KAPAS inhibitory effect. In addition, the juglon of the present invention showed an inhibitory effect on KAPAS in a concentration-dependent manner, IC ₅₀ was confirmed to be 9.1 μM level (see Fig. 1).

In a specific embodiment of the present invention, the present inventors, in order to confirm the control effect of the visible foil in the greenhouse conditions, as a result of treatment with the concentration of 1000 μg / ㎖ of the present invention in the visible foil of the greenhouse conditions, within 1 to 3 hours Outward symptoms were manifested by fast-acting, 90% after 1 day of treatment, and 4 days after treatment, it was confirmed that thorny sac was completely killed (see Table 1 and FIG. 2).

In a specific embodiment of the present invention, the present inventors, in order to confirm the effect of the control of the visible foil in the packaging conditions, as a result of treating the concentration of the juglon 1000 ㎍ / ㎖ or 2000 ㎍ / ㎖ of the present invention in the packaging foil, Outward symptoms were manifested by fast-acting within 1 to 3 hours, it was confirmed that after 5 hours of treatment depending on time, 60 to 70% control effect, and 70 to 80% control effect after 8 days of treatment (Table 2 and FIG. 3).

Therefore, the juglone of the present invention or a pharmaceutically acceptable salt thereof has a function of 7-keto-8-aminopelargonic acid synthase (KAPAS), which plays a major role in plant growth by participating in the biotin biosynthetic pathway of microorganisms and plants. Inhibiting and showing significant herbicidal activity against barley gourd causing severe damage in all areas of Korea, it can be usefully used as an active ingredient of a safe natural herbicide of the human body.

The active compounds of formula (I) according to the invention are solutions, emulsions, hydrating powders, suspensions, powders, sprays, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic substances impregnated with the active compounds, and It can be converted into a conventional formulation such as microcapsules in the polymer.

These formulations may be prepared by known methods, for example by mixing the active compound with an extender, ie a liquid solvent and / or a solid carrier, optionally using surfactants, ie emulsifiers and / or dispersants and / or foam formers. have.

If the extender used is water, for example an organic solvent can also be used as an auxiliary solvent. Suitable liquid solvents include mainly aromatic compounds such as xylene, toluene or alkylnaphthalene, chlorinated aromatic and chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride, cyclohexane or paraffins, for example petroleum fractions, mineral oils and vegetable oils. Groups of aliphatic hydrocarbons, alcohols such as butanol or glycol and ethers and esters thereof, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethylformamide and dimethylsulfoxide and water It may be one or more selected from.

Suitable solid carriers can be, for example, ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as finely divided silica, alumina and silicates. Suitable solid carriers for granules are, for example, granulated and classified natural rocks such as calcite, marble, pumice, hemastone and dolomite, and synthetic granules of inorganic and organic powders, and organics such as sawdust, coconut shells, cornstalks and tobacco stalks. It is a granule of matter. Suitable emulsifiers and / or foam formers are, for example, nonionic and anionic emulsifiers, for example polyoxyethylene fatty alcohol ethers such as polyoxyethylene fatty acid esters, alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, aryls Sulfonates and protein hydrolysates. Suitable dispersants can be, for example, lignin-sulfite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids such as cephalin and lecithin, and synthetic phospholipids Can be used. Other possible additives include mineral and vegetable oils.

Colorants such as inorganic pigments such as iron oxide, titanium oxide and prussian blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes and salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc Micronutrients can be used.

Such herbicides may generally contain an active compound of Formula 1 in an amount of 0.1 to 95% by weight, preferably 0.5 to 90% by weight, but is not limited thereto.

When controlling weeds, the active compounds according to the invention can be used on their own or as a mixture with other known herbicides, and finished product preparations or tank mixes are possible.

Known herbicide components that can be mixed include acetochlor, acifluorophene (-sodium), acloniphene, alachlor, alkoxydim (-sodium), amethrin, amidochlor, amidosulfuron, anilophos, Asulam, Atrazine, Azaphenidine, Azimsulfuron, Benazolin (-ethyl), Benfuresate, Bensulfuron (-methyl), Bentazone, Benzobicyclone, Benzophene, Benzoylprop (-ethyl), B Alafos, biphenox, bispyribac (-sodium), bromobutide, bromophenoxime, bromocinyl, butachlor, butoxydim, butyrate, carfenstrol, caloxydim, carbetamid, car Pentrazone (-ethyl), clomethoxyphene, chlorrambene, chloridazone, chlorimuron (-ethyl), chlornitrophene, chlorsulfuron, chlortoluron, cinidon (-ethyl), citrine, Cynosulfuron, clepoxydim, cletodim, clodinapop (-propargyl), clomazone, clomeprop, clopyralide, clo Ropyrasulfuron (-methyl), chloransullam (-methyl), cumyluron, cyanazine, cybutrin, cycloate, cyclosulfamuron, cyanoxydim, cyhalofop (-butyl), 2 , 4-D, 2,4-DB, 2,4-DP, desmedipham, dialylate, dicamba, diclofo (-methyl), diclosullam, dietathyl (-ethyl), dipfenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiferrate, Dimethaclor, Dimethamethrin, Dimethenamid, Dimexiflom, Dinitramine, Diphenamide, Diquat, Dithiopyr, Diuron , Dimron, epoprodan, EPTC, esprocarb, etafluralin, etamethsulfuron (-methyl), etofumesate, ethoxyphene, ethoxysulfuron, etobenzanide, phenoxaprop (-P -Ethyl), pentrazamide, flamprop (-isopropyl), flamprop (-isopropyl-L), flamprop (-methyl), plazasulfuron, florasilam, fluazifop (-P- Butyl), fluazolei , Flucarbazone, flufenacet, flumetsulam, flumichlorak (-pentyl), flumioxazine, flumipropine, flumetsulam, fluoromethuron, fluorochloridone, fluoroglycopene ( -Ethyl), flupoxam, flupropacyl, flupyrsulfuron (-methyl, -sodium), flurenol (-butyl), flulidone, fluoxypyr (-methyl), fluprimidol, flu Tamone, fluthiacet (-methyl), flutiamide, pomesaphene, glufosinate (-ammonium), glyphosate (-isopropylammonium), halosafen, halooxyphosph (-ethoxyethyl), halooxy Pope (P-methyl), hexazinone, imazamethabenz (-methyl), imazamethapir, imazamox, imazapic, imazaphyr, imazaquin, imazetapyr, imazasulfuron, iodosulfuron ( -Methyl, -sodium), isoxynyl, isoprophalin, isoproturon, isourone, isoxaben, isoxachlortol, isoxaflutol, isoxapyrifop, lac Tofen, lenacil, linuron, MCPA, MCPP, mefenacet, mesotrione, metamitrone, metazachlor, metabenzthiazuron, methopenzuron, methopromurolone, (alpha-) metolachlor, Metosullam, Methoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Duck Truncated, oxadiargyl, oxadione, oxasulfuron, oxaziclomepon, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralline, pentoxazone, penmedipalm, piperophosph, Pretilachlor, primisulfuron (-methyl), promethrin, propachlor, propanyl, propazazapov, propisochlor, propizamide, prosulfocarb, prosulfuron, pyraflufen (- Ethyl), pyrazolate, pyrazosulfuron (-ethyl), pyrazoxifen, pyribenzoxime, pyributicab, pyridate, blood Minobac-(-methyl), pyrithiobac (-sodium), quinclolac, quinmerac, quinoclammine, quizaropof (-P-ethyl), quinazulfop (-P-tefuryl), rimsulfuron , Cetoxydim, Simazine, Cimetrin, Sulkotlion, Sulfentrazone, Sulfomethuron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebutiuron, Tepraloxydim, Tebutylazine , Terbutrin, tenylchlor, thiafluamide, thiazopyr, thiadiazimine, thifensulfuron (-methyl), thiobencarb, thiocarbazil, tralcoxysid, trialate, triasulfuron, tri It may be, but is not limited to, at least one selected from the group consisting of benuron (-methyl), triclopyr, tridiphane, trituralin, and triflusulfuron.

Mixtures with other known active compounds are also possible, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and soil remediators.

The active compounds can be used on their own, in the form of their preparations or in the form of uses prepared from them by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, sprays, pastes and granules. The active compounds are used by conventional methods, for example by watering, spraying, atomizing or scattering.

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

The juglon inhibits KAPAS activity.

The juglon is preferably treated at a concentration of 500 to 2,500 μg / ml, and more preferably at a concentration of 1,000 to 2,000 μg / ml, but is not limited thereto.

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> Zuglon ( Juglone ) Preparation of Compound

The natural naphthoquinone compound juglon (5-hydroxynaphthoquinone) derived from the Juglandaceae family black walnut It was purchased from Sigma-Aldrich (Formula 1). In addition, the commercially available purity of juglon is 90% or more by HPLC, and further purified by HPLC prior to the experiment.

< Example  2> KAPAS  Measurement of inhibitory activity

Arabidopsis thaliana ) derived AtKAPAS protein was used to measure the inhibitory activity against KAPAS.

Specifically, KAPAS inhibitory activity is a microplate spectrophotometer (Benchmark Plus, Bio-) with a thermostat adjusted to 30 ° C. according to the method described in SP Webster et al., Biochemistry 39 (2000) 516-528. rad, USA) was confirmed by observing the increase in NADH absorption at 340 nm. The reaction solution for the determination of KAPAS enzyme activity was 20 mM potassium phosphate (pH 7.5), 1 mM a-ketoglutarate, 0.25 mM thiamine pyrophosphate in a total volume of 200 µl. , 1 mM NAD ⁺ , 3 mM MgCl ₂ , 0.1 unit a-ketoglutarate dehydrogenase, and 2-10 μg KAPAS were added, L-Alanine and O. Ploux, A. Marquet, Biochem. Pimeloyl-CoA synthesized according to the method described in J. 283 (1992) 327-331 was measured by adding the final concentration to each reaction solution. Prior to analysis, enzyme samples were dialyzed against 20 mM potassium phosphate (pH 7.5) containing 100 μM pyridoxal 5′-phosphate (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 concentration of juglon was treated at 0.5, 1, 2, 4, 8 and 16 μΜ concentrations. As a control for measuring enzyme activity, cuvettes containing other ingredients except zoglon were used.

As a result, as shown in Figure 1, it was confirmed that the juglon of the present invention has the strongest inhibitory effect on KAPAS in a concentration-dependent manner, IC ₅₀ was 9.1 μM (Fig. 1).

< Example  3> Zuglon Thorny night  Confirmation of Control Effect

<3-1> Prickly  Ready

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.

<3-2> under greenhouse conditions Thorny night  Confirmation of Control Effect

The final treated concentration of juglon was weighed to a concentration of 1,000 μg / ml in the thorn gourd prepared in Example <3-1> and dissolved in 1 ml of acetone, followed by pharmaceutical preparation (acetone 50%, Tween-20 0.1%). Diluted preparation was 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, as shown in Table 1 and Figure 2, the treatment of juglon to spiny gourd manifests an external symptom within 1 to 3 hours of drug treatment, which is very fast-acting and shows 90% control effect after 1 day of drug treatment. After 4 days, the complete control (100%), the growth point was confirmed that the regeneration was not over time (Table 1 and Figure 2).

compound

Treatment concentration
(Μg / ml) Control effect 1 DAT ^* 4 DAT Zuglon 1,000 90 100

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

<3-3> in packing condition Thorny night  Confirmation of Control Effect

In Example <3-2> Juglon which confirmed the control effect of thorns The activity was confirmed in the packaging conditions.

Specifically, the field test was conducted in September 2011 at the Namhan Riverside located at 31-15, Andeok-ri, Gaegun-myeon, Yangpyeong-gun, Gyeonggi-do, Korea. The degree was 10 ~ 15 leaves and the length was over 2-3m. Juglon was diluted to a concentration of 1,000 and 2,000 μg / ml in a 50% acetone solution containing 0.1% Tween-20 and treated 300 ml per compartment. The experiment was repeated three times of 1 m ² land size and was assessed by visual rating scale of 0-100 on days 5, 8 and 14 after Zuglon 1,000 and 2,000 μg / ml treatment.

As a result, as shown in Table 2 and FIG. 3, the spinach was dried or disappeared within 1 to 3 hours after treatment with juglon, and control effects at 1,000 and 2,000 µg / ml treatment concentrations after 5 days were 60% and 70%, respectively. The control effect at the same concentration was 70% and 80%, respectively, even after 8 days of treatment. In addition, the residual activity lasted for 2 weeks without any regeneration field. Therefore, the juglon of the present invention is significantly controlled within the concentration range in which the thorny plants designated as weeds for the environment are treated not only in greenhouse conditions but also in weather conditions such as rainfall or temperature change, or pavement conditions that are easily decomposed by light. It was confirmed that.

compound
Treatment concentration
(Μg / ml) Control effect (%) 5 DAT ^* 8 DAT Zuglon 1,000 60 70 2,000 70 80

Claims (10)

To visible foil (Sciyos containing primary geulron (Juglone) or a pharmaceutically acceptable salt thereof represented by the general formula (1) as an active ingredient angulatus L. Control herbicide composition:
[Formula 1]

.
The herbicide composition for controlling thorn foil according to claim 1, wherein the juglon is derived from black walnut.
According to claim 1, wherein the juglon is a herbicide composition for the control of barbed gourd, characterized in that to inhibit KAPAS (7-keto-8-aminopelargonic acid synthase) activity.
According to claim 1, wherein the juglon is a herbicide composition for control of the visible foil, characterized in that the treatment at a concentration of 500 to 2,500 ㎍ / ㎖.
The method of claim 1, wherein the juglon is treated with a herbicide composition for control of thorn foil, characterized in that the treatment at a concentration of 1,000 to 2,000 ㎍ / ㎖.
A spiny herbicide method comprising treating a spiny herbicide herbicide composition containing juglon represented by the formula (1) or a pharmaceutically acceptable salt thereof as an active ingredient to prickly gourd, its seeds or its habitat.
7. The method of claim 6, wherein the juglon inhibits KAPAS activity.
7. The method of claim 6, wherein the juglon is treated at a concentration of 500 to 2,500 µg / ml.
7. The method of claim 6, wherein the juglon is treated at a concentration of 1,000 to 2,000 [mu] g / ml.
7. The method of claim 6, wherein the herbicide composition for controlling prickly pear is irrigated, sprayed, or coated on a plant in a liquid state or immersed in a seed of a crop.

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