Composition for destroying microalgae comprising vitamin k derivative and uses thereof

Abstract

The present invention relates to a composition for destroying microalgae comprising a vitamin K derivative and uses thereof. According to one aspect, the composition for destroying microalgae can be applied to marine microalgae culture sites, areas where green tides or red tides have occurred, or areas where green tides or red tides are expected to occur, thereby inhibiting the growth and proliferation of microalgae and preventing damage caused by green tides and red tides.

Description

Composition for destroying microalgae containing a vitamin K derivative and the use thereof

[0001] The present invention relates to a composition for destroying microalgae comprising a vitamin K derivative and the use thereof.

[0002] As aquatic ecosystems around the world change due to global warming, algal blooms—in which phytoplankton grow rapidly—are occurring in freshwater sources such as dams and reservoirs, posing a critical problem for securing water resources, including drinking water. Due to these algal blooms, the United States suffers losses of approximately $4 billion or more annually, while Japan incurs costs of tens of millions of dollars annually due to mass fish deaths.

[0003] Algae are aquatic plants containing chlorophyll that perform photosynthesis, and an uncontrollable growth of algal colonies is called a Harmful Algal Bloom (HAB). Generally, the term "green algae" is used to refer to outbreaks caused by algae or cyanobacteria. HABs caused by harmful algae typically occur during warm summers or early autumn due to high water temperatures, sunlight, excessive influx of organic matter, stagnant and slow water flow, and eutrophication resulting from increased concentrations of nutrients such as nitrogen and phosphorus. HABs not only cause foul odors but also form "dead zones" in enclosed spaces. As algae die and decompose in a state of mass bloom, oxygen is depleted through microbial decomposition, creating conditions of hypoxia or anoxia that lead to oxygen deficiency in marine organisms and fish mortality.

[0004] Against this background, the inventors developed a compound capable of effectively removing the aforementioned algae or microalgae, and confirmed its excellent efficacy to complete the present invention.

[0005] One aspect provides a composition for destroying microalgae, comprising a compound represented by the following chemical formula 7, a stereoisomer thereof, a salt thereof, a hydrate thereof, or a solvate thereof:

[0006] [Chemical Formula 7]

[0007]

[0008] In the above chemical formula 7,

[0009] A1 and A2 are each independently hydrogen, deuterium, and substituted or unsubstituted C1-C 10 Selected from alkyl groups, and

[0010] A3 is independently hydrogen, deuterium, substituted or unsubstituted C1-C 10 Alkyl groups, substituted or unsubstituted C2-C 10 alkenyl groups, substituted or unsubstituted C2-C 10 alkynyl group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C2-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted C2-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C3-C 10 Aryl groups, and substituted or unsubstituted C2-C 10 Selected from heteroaryl groups,

[0011] A4 is hydrogen, deuterium, and substituted or unsubstituted C1-C 10 Selected from alkyl groups, and

[0012] A5 is each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -OH, cyano group, nitro group, amino group, amidino group, substituted or unsubstituted C1-C 10 Alkyl groups, substituted or unsubstituted C2-C 10 alkenyl groups, substituted or unsubstituted C2-C 10 alkynyl group, substituted or unsubstituted C1-C 10 Alkoxy groups, substituted or unsubstituted C3-C10 Cycloalkyl group, substituted or unsubstituted ternary to 10-membered heterocycloalkyl group, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted ternary to decary heterocycloalkenyl group, substituted or unsubstituted C3-C 10 Aryl group, substituted or unsubstituted C3-C 10 Aryloxy group, substituted or unsubstituted C3-C 10 Selected from an arylthio group and a substituted or unsubstituted 3 to 10-membered heteroaryl group,

[0013] m is selected from integers 1 to 10, and

[0014] n is selected from integers 0 to 4.

[0015] Another aspect provides a method for destroying microalgae, comprising the step of treating a marine microalgae culture facility, an area where green or red tide occurs, or an area where green or red tide is expected to occur with the above-mentioned composition for destroying microalgae.

[0016] Another aspect provides a composition for improving water quality comprising a compound represented by the above chemical formula 7, a stereoisomer thereof, a salt thereof, a hydrate thereof, or a solvate thereof.

[0017] Another aspect provides a method for improving water quality, comprising the step of treating a marine microalgae culture facility, an area where green or red tide occurs, or an area where green or red tide is expected to occur with the above-mentioned water quality improvement composition.

[0018] One aspect provides a composition for destroying microalgae, comprising a compound represented by the following chemical formula 7, a stereoisomer thereof, a salt thereof, a hydrate thereof, or a solvate thereof:

[0019] [Chemical Formula 7]

[0020]

[0021] In the above chemical formula 7,

[0022] A1 and A2 are each independently hydrogen, deuterium, and substituted or unsubstituted C1-C 10 Selected from alkyl groups, and

[0023] A3 is independently hydrogen, deuterium, substituted or unsubstituted C1-C 10 Alkyl groups, substituted or unsubstituted C2-C 10 alkenyl groups, substituted or unsubstituted C2-C 10 alkynyl group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C2-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted C2-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C3-C 10 Aryl groups, and substituted or unsubstituted C2-C 10 Selected from heteroaryl groups,

[0024] A4 is hydrogen, deuterium, and substituted or unsubstituted C1-C 10 Selected from alkyl groups, and

[0025] A5 is each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -OH, cyano group, nitro group, amino group, amidino group, substituted or unsubstituted C1-C 10 Alkyl groups, substituted or unsubstituted C2-C 10 alkenyl groups, substituted or unsubstituted C2-C 10 alkynyl group, substituted or unsubstituted C1-C 10 Alkoxy groups, substituted or unsubstituted C3-C 10 Cycloalkyl group, substituted or unsubstituted ternary to 10-membered heterocycloalkyl group, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted ternary to decary heterocycloalkenyl group, substituted or unsubstituted C3-C 10 Aryl group, substituted or unsubstituted C3-C 10 Aryloxy group, substituted or unsubstituted C3-C 10Selected from an arylthio group and a substituted or unsubstituted 3 to 10-membered heteroaryl group,

[0026] m is selected from integers 1 to 10, and

[0027] n is selected from integers 0 to 4.

[0028] The compound of the above chemical formula 7 may include a vitamin K derivative.

[0029] The definitions of terms used in the chemical formulas of this specification are as follows.

[0030] The term "alkyl" used in chemical formulas refers to a fully saturated branched or unbranched (or straight-chain or linear) hydrocarbon group. Non-limiting examples of the "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, ter-butyl group, n-pentyl, isopentyl, neopentyl, iso-amyl, n-hexyl, 3-methylhexyl, 2,2-dimethylpentyl, 2,3-dimethylpentyl, n-heptyl, etc.

[0031] The term "halogen" used in chemical formulas includes fluorine (-F), bromine (-Br), chlorine (-Cl), iodine (-F), etc.

[0032] The term "alkoxy" used in the chemical formula represents alkyl-O-, and the alkyl is as described above. Non-limiting examples of the alkoxy include methoxy, ethoxy, propoxy, 2-propoxy, butoxy, tert-butoxy, pentyloxy, hexyloxy, cyclopropoxy, cyclohexyloxy, etc.

[0033] The term "alkenyl" as used in chemical formulas refers to a branched or unbranched hydrocarbon having at least one carbon-carbon double bond. Non-limiting examples of alkenyls include vinyl, allyl, butenyl, isopropenyl, isobutenyl, etc.

[0034] The term "alkynyl" used in the chemical formula refers to a branched or unbranched hydrocarbon having at least one carbon-carbon triple bond. Non-limiting examples of the alkynyl include ethinyl, butynyl, isobutynyl, isopropynyl, etc.

[0035] The term "cycloalkyl" used in chemical formulas refers to a ring-forming alkyl group. The said alkyl group is as described above. Non-limiting examples of the said cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. Additionally, "cycloalkenyl" refers to a ring-forming alkenyl group, and the said alkenyl group is as described above.

[0036] The term "heterocycloalkyl" as used in chemical formulas refers to a cyclic hydrocarbon that is entirely saturated and contains one or more heteroatoms selected from N, O, P, or S as a reducing agent. Additionally, "heterocycloalkenyl" refers to a cyclic hydrocarbon that contains one or more heteroatoms selected from N, O, P, or S as a reducing agent and has at least one double bond.

[0037] The term "aryl" used in chemical formulas refers to an aromatic hydrocarbon containing one or more rings, used alone or in combination. The term "aryl" also includes groups in which an aromatic ring is fused to one or more cycloalkyl rings. Non-limiting examples of the "aryl" include phenyl, naphthyl, tetrahydronaphthyl, etc.

[0038] The term "heteroaryl" used in chemical formulas refers to a monocyclic or bicyclic organic compound comprising one or more heteroatoms selected from N, O, P, or S, and having a remaining ring atom that is carbon. The heteroaryl group may, for example, contain 1 to 5 heteroatoms and may contain 3 to 12 ring members. The S or N may be oxidized to have various oxidation states.

[0039] The term "amino group" used in chemical formulas indicates a case where a nitrogen atom is covalently bonded to at least one carbon or heteroatom. Amino groups include, for example, -NH2 and substituted moieties. The term "amino group" may include alkylaminos in which nitrogen is bonded to at least one additional alkyl group, arylaminos in which nitrogen is bonded to at least one or more independently selected aryl groups, and diarylaminos.

[0040] In this specification, the terms “substituted” or “substituent” refer to a group in which one or more hydrogen atoms are replaced by one or more non-hydrogen atoms, provided that the valence requirement is satisfied and a chemically stable compound results from the substitution. Within this specification, unless explicitly stated as “unsubstituted,” all substituents shall be interpreted as being capable of being substituted or unsubstituted.

[0041] For example, the term "substituted" used in "substituted" in the above-mentioned alkyl groups, haloalkyl groups, alkoxy groups, alkylamino groups, alkenyl groups, alkynyl groups, cycloalkyl groups, cycloalkenyl groups, heterocycloalkyl groups, heterocycloalkenyl groups, aryl groups, and heteroaryl groups, etc., refers to C1-C10 alkyl groups in which one or more hydrogen atoms are substituted with a halogen (e.g., CF3, CHF2, CH2F, CCl3, etc.), alkoxy groups, hydroxyl groups, nitro groups, cyano groups, amino groups, amide groups, sulfonamide groups, ketone groups, ester groups, alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, cycloalkenyl groups, heterocycloalkyl groups, heterocycloalkenyl groups, aryl groups, arylalkyl, aryloxy, heteroaryl groups, heteroarylalkyl, and It may be substituted with heteroaryloxy, etc.

[0042] In one embodiment, the substitution is one or more R a It may be substituted with, and the above one or more Ra Each independently consists of hydrogen, deuterium, -F, -Cl, -Br, -I, -OH, cyano group, nitro group, amino group, amidino group, substituted or unsubstituted C1-C10 Alkyl group, substituted or unsubstituted C1-C10 haloalkyl group, substituted or unsubstituted C2-C10 Alkenyl group, substituted or unsubstituted C2-C10 alkynyl group, and substituted or unsubstituted C1-C10 It may be selected from a group composed of alkoxy groups.

[0043] The terms “salt thereof” or “acceptable salt” in this specification refer to a form of salt that can be used among substances in which cations and anions are bonded by electrostatic attraction, and typically include metal salts, salts with organic bases, salts with inorganic acids, salts with organic acids, salts with basic or acidic amino acids, etc. For example, metal salts may include alkali metal salts (sodium salts, potassium salts, etc.), alkaline earth metal salts (calcium salts, magnesium salts, barium salts, etc.), aluminum salts, etc.; salts with organic bases may include salts with triethylamine, pyridine, picoline, 2,6-rutidine, ethanolamine, diethanolamine, triethanolamine, cyclohexylamine, dicyclohexylamine, N,N-dibenzylethylenediamine, etc.; and salts with inorganic acids may include salts with hydrochloric acid, hydrobromide, nitric acid, sulfuric acid, phosphoric acid, etc. Salts with organic acids may include formic acid, acetic acid, trifluoroacetic acid, phthalic acid, fumaric acid, oxalic acid, tartaric acid, maleic acid, citric acid, succinic acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, etc.; salts with basic amino acids may include arginine, lysine, ornithine, etc.; and salts with acidic amino acids may include aspartic acid, glutamic acid, etc. Particularly desirable salts include inorganic salts such as alkali metal salts (e.g., sodium salts, potassium salts, etc.) and alkaline earth metal salts (e.g., calcium salts, magnesium salts, barium salts, etc.) and organic salts such as ammonium salts when the compound has acidic functional groups therein, and salts with inorganic acids such as hydrochloric acid, hydrobromide, nitric acid, sulfuric acid, phosphoric acid, etc. and salts with organic acids such as acetic acid, phthalic acid, fumaric acid, oxalic acid, tartaric acid, maleic acid, citric acid, succinic acid, methanesulfonic acid, p-toluenesulfonic acid, etc. when the compound has basic functional groups therein.

[0044] In this specification, the term "isomer" in "stereoisomer" refers to a compound that has the same molecular formula but differs in the way constituent atoms are connected or in their spatial arrangement within the molecule. Isomers include, for example, structural isomers and stereoisomers. The stereoisomers may be diasteromers or enantiomers. Enantiomers are isomers that do not overlap with their mirror images, much like the relationship between a left hand and a right hand, and are also called optical isomers. Enantiomers are classified as R (Rectus: clockwise) and S (Sinister: counterclockwise) when four or more substituents on the chiral central carbon differ. Diastereomers are stereoisomers that are not mirror images of each other, and can be divided into cis and trans isomers due to differences in the spatial arrangement of atoms.

[0045] The term "solvate" in this specification refers to a compound solvated in an organic or inorganic solvent. The solvate may be, for example, a hydrate.

[0046] In the above chemical formula 7, A1 and A2 are each independently hydrogen, deuterium, and substituted or unsubstituted C1-C 10 It may be selected from alkyl groups, and specifically, A1 and A2 may each be independently selected from hydrogen, substituted or unsubstituted methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, and heptyl group.

[0047] In one embodiment, A1 and A2 may each be independently selected from the group consisting of hydrogen, a substituted or unsubstituted methyl group and a substituted or unsubstituted ethyl group, and specifically may be a substituted or unsubstituted methyl group.

[0048] In the above chemical formula 7, A3 is hydrogen, deuterium, substituted or unsubstituted C1-C 10 It may be selected from alkyl groups, and specifically, the above A3 may each be independently selected from hydrogen, substituted or unsubstituted methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, and heptyl group.

[0049] In one embodiment, A3 may be selected from hydrogen and a substituted or unsubstituted C1-C5 alkyl group, and specifically may be hydrogen.

[0050] In the above chemical formula 7, A4 is hydrogen, deuterium, and substituted or unsubstituted C1-C 10 A4 is selected from among alkyl groups, and specifically, each A4 may be independently selected from hydrogen, substituted or unsubstituted methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, and heptyl group.

[0051] In one embodiment, the A4 may be selected from the group consisting of hydrogen and a substituted or unsubstituted methyl group.

[0052] In the above chemical formula 7, the -(CH2) m - may be a substituted or unsubstituted alkylene, and the above -(CH2) m - In this case, one or more hydrogens can be substituted independently.

[0053] In one embodiment, the above -(CH2) m- m may be selected from integers from 1 to 10, specifically m may be an integer from 1 to 10, 1 to 8, 1 to 6, 1 to 4, 1 to 3, 2 to 10, 2 to 8, 2 to 6, 2 to 4, or 2 to 3, and more specifically m may be 2 or 3.

[0054] In one embodiment, the compound of Formula 7 may comprise one or more compounds selected from the group consisting of the following compounds 1 to 6, and the composition may comprise one or more compounds selected from the group consisting of the following compounds 1 to 6, a salt thereof, a hydrate thereof, or a solvate thereof:

[0055] .

[0056] In one embodiment of the present invention, the compound can be isolated from nature or prepared by a chemical synthesis method known in the art, and typically, it can be prepared by reacting substituent compounds with a suitable reaction solvent to obtain an intermediate product, and then reacting the intermediate product in a suitable reaction solvent.

[0057] There are no specific restrictions on the reaction solvents that can be used in the above manufacturing process as long as they do not participate in the reaction. Examples include ethers such as diethyl ether, tetrahydrofuran, and dioxane; halogenated hydrocarbons such as dichloromethane and chloroform; amines such as pyridine, piperidine, and triethylamine; acetone; alkyl ketones such as methyl ethyl ketone and methyl isobutyl; alcohols such as methanol, ethanol, and propanol; and non-protonic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, and hexamethyl phosphate triamide. In particular, among non-reactive organic solvents commonly used in organic synthesis, solvents capable of separating water generated during the reaction by the Dean-Stack trap are preferred. Examples of such solvents include benzene, toluene, and xylene, but are not limited thereto. The separation and purification of reaction products are carried out through processes such as concentration and extraction, which are typically performed in organic synthesis, and, if necessary, separation and purification can be performed through purification by column chromatography on silica gel.

[0058] The present invention also includes any modification to the methods for preparing compounds according to one embodiment of the present invention, wherein an intermediate product obtainable at any step thereof may be used as a starting material for the remaining steps, said starting material may be formed within the reaction system under reaction conditions, or the reaction components may be used in the form of their salt or optically enantiomer.

[0059] In addition, depending on the type of substituents used to prepare the compound according to the present invention, the intermediate product, and the choice of preparation method, possible isomers, such as substantially pure geometric (cis or trans) isomers, optical isomers (enantiomers), or racemic forms, all of which are included within the scope of the present invention.

[0060] In one embodiment, a composition comprising a compound represented by Chemical Formula 7, a stereoisomer thereof, a salt thereof, a hydrate thereof, or a solvate thereof may control / inhibit the growth of microalgae, reduce their activity, and / or induce death. Accordingly, the composition has algicidal activity and can be used as an algicidal agent.

[0061] The terms “microalgae” or “algae” in this specification refer to algae capable of causing green algae or red algae and algae capable of producing biodiesel, and the microalgae may include one or more selected from the group consisting of cyanobacteria, diatoms, green algae, red algae, euglenoid algae, flagellates, yellow-green algae, dinoflagellates, scleroflavinates, and algae capable of producing biodiesel.

[0062] The above cyanobacteria may be selected from algae of the genera Microcystis, Anabaena, Aphanizomenon, and Oscillatoria, but are not limited thereto.

[0063] The above diatoms may be selected from algae of the genera Synedra, Asterionella, Cyclotella, Melosira, Skeletonema costatum, Chaetoceros, Thalassiosira, Leptocylindrus, Nitzschia, Cylindrotheca, Eucampia, and Odontella, but are not limited thereto.

[0064] The above green algae may be selected from algae of the genera Closterium, Pediastrum, Selenastrum, Chlorella, and Scenedesmus, but are not limited thereto.

[0065] The above red algae may be selected from algae of the genera Chattonella, Heterosigma, and Cocholodinium, but are not limited thereto.

[0066] The above-mentioned Euglenoids may be algae of the genus Trachelomonas or Euglena, but are not limited thereto.

[0067] The above-mentioned flagellates may be selected from algae of the genera Peridinium, Heterosigma, Heterocapsa, Cochlodinium, Prorocentrum, Ceratium, Noctiluca, Scrippsiella, Dinophysis, Alexandrium, Eutreptiella, Pfiesteria, Chattonella, Emiliania, and Gymnodinium, but are not limited thereto.

[0068] The above yellow-green algae may be algae of the genus Uroglena, but are not limited thereto.

[0069] The above dinoflagellates and above scleroflavinates may be selected from algae of the genera Heterosigma, Heterocapsa, Cochlodinium, Prorocentrum, Ceratium, Noctiluca, Scrippsiella, dinophysis, Alexandrium, Eutreptiella, Pfiesteria, Chattonella, Emiliania, and Gymnodinium, but are not limited thereto.

[0070] The algae capable of producing the above biodiesel may be selected from among algae of the genera Pseudochoricystis, Botryococcus, and Dunaliella, but are not limited thereto.

[0071] In one embodiment, the microalgae may comprise one or more microalgae selected from the group consisting of Microcystis, Anabaena, Chlorella, Selenastrum, Cochlodinium, Heterosigma, and combinations thereof.

[0072] In one embodiment, the microalgae may comprise one or more microalgae selected from the group consisting of Microcystis aeruginosa, Anabaena, Chlorella Vulgaris, Selenastrum Gracile, Cochlodinium polykrikoides, and Heterosigma.

[0073] The compound represented by the above chemical formula 7, its stereoisomer, its salt, its hydrate, or its solvate, or a composition for destroying microalgae containing the same may have no or significantly low toxicity to aquatic organisms, and specifically, may not exhibit toxicity to aquatic organisms other than algae (specifically water fleas and / or zebrafish), and may not inhibit their growth, development, and / or activity.

[0074] In one embodiment, the composition may be used to prevent the occurrence of green or red tides caused by microalgae. In this case, since the amount of microalgae is small and the residual composition can prevent the occurrence of microalgae, it may be advantageous to further reduce the amount of composition sprayed. However, even in this case, since the dead microalgae may contribute to the occurrence of green or red tides as nutrients, the method may further include steps such as physical filtration, chemical treatment, or generating bubbles, as in the treatment method within or outside the water system.

[0075]

[0076] Another aspect provides a method for destroying or removing microalgae, comprising the step of applying the above-described composition for destroying microalgae to a marine microalgae culture facility, an area where green or red tides occur, or an area where green or red tides are expected to occur. The same parts as described above apply equally to the above method.

[0077] In this specification, the term "region" refers to a place having an environment where green algae or red tides may occur, and includes all aquatic environments containing both seawater and freshwater. Additionally, the term "treatment" refers to bringing the composition into contact with microalgae, and may include a step of introducing the composition into an aquatic system containing microalgae for such contact, wherein the introduction may be carried out by spraying it onto the water surface in the form of a spray, including a stirring step, or moving it over the water surface.

[0078] In one embodiment, when the composition for destroying microalgae, specifically one or more compounds selected from the group consisting of Formulas 1 to 6 of the present invention, stereoisomers thereof, salts thereof, hydrates thereof, or solvates thereof, is applied to a marine microalgae culture site, an area where green algae or red tide has occurred, or an area where green algae or red tide is expected to occur, it may be used in a range of 1 μM to 100 μM, for example, a range of 1 μM to 30 μM, based on the final concentration in the treatment area.

[0079] In one embodiment, the method may utilize an "external water system treatment method." The term "external water system treatment method" refers to drawing up water from a water system, treating it with the microalgae destruction composition to remove microalgae, and then discharging the treated water back into the water system. The term "water system" refers to a source of water and may include, for example, natural water systems such as reservoirs, lakes, and rivers, as well as artificial water systems such as fish farms, fishing grounds, cultivation facilities, golf courses, and water tanks. Specifically, the method may include the steps of: drawing raw water containing microalgae from the water system; treating the raw water with the composition; and discharging the treated water back into the water system. To prevent red tides or green algae caused by nutrients that may occur if the treated water is discharged as is, the method may further include the step of removing residual composition, residual microalgae, organic matter, nutrients, and dead microalgae. The above removal step may include physical methods such as precipitation, solid-liquid separation, or simple filtration, or chemical methods using copper sulfate, chlorine-based substances, ultraviolet rays, or ozone, etc.

[0080] In one embodiment, the method may utilize a "treatment method within a water system." The term "treatment method within a water system" refers to removing microalgae by spraying a composition into a water system. Since the composition has low toxicity to other organisms compared to its toxicity to algae, it may be used to treat microalgae by spraying it within an appropriate range at an appropriate concentration. The concentration may be adjusted according to the type of water system to be sprayed, pH, salinity, temperature, composition, area, depth, use, or distribution of aquatic organisms, the type, concentration, or distribution of microalgae to be treated, or the purpose or goal of microalgae destruction. The "treatment method within a water system" may also include additional steps for removing other residual compositions, residual microalgae, organic matter, nutrients, and dead microalgae, similar to the "treatment method outside a water system." The removal step may include methods such as physically filtering using filter paper, or removing the microalgae after floating them by spraying a coagulant together or sequentially. The above removal step may also include a step of generating bubbles to supply oxygen to the water, increase efficiency, and allow the aggregates to float without settling.

[0081]

[0082] Another aspect is to provide an algaecide composition comprising a compound represented by the above chemical formula 7, a stereoisomer thereof, a salt thereof, a hydrate thereof, or a solvate thereof. The same parts as described above apply equally to the above composition.

[0083] The above algaecide composition has algicidal activity against algae and may be used for controlling algae.

[0084]

[0085] Another aspect provides a composition for improving water quality comprising a compound represented by the above chemical formula 7, a stereoisomer thereof, a salt thereof, a hydrate thereof, or a solvate thereof. The same as described above applies equally to the composition.

[0086] The above water quality improvement may include inhibiting the growth of microalgae, reducing their activity, and / or inducing their death.

[0087]

[0088] Another aspect provides a method for improving water quality, comprising the step of treating a marine microalgae culture facility, an area where green or red tides occur, or an area where green or red tides are expected to occur with the above-described water quality improvement composition. The same parts as described above also apply to the above method.

[0089] The above water quality improvement method may improve water quality by inhibiting the growth of microalgae, reducing their activity, and / or inducing their death.

[0090]

[0091] Another aspect is to provide a use for destroying or removing microalgae of a composition comprising a compound represented by the chemical formula 7 below, a stereoisomer thereof, a salt thereof, a hydrate thereof, or a solvate thereof. The same parts as described above apply equally to the said use.

[0092]

[0093] Another aspect is to provide a use for improving water quality of a composition comprising a compound represented by the chemical formula 7 below, a stereoisomer thereof, a salt thereof, a hydrate thereof, or a solvate thereof. The same parts as described above apply equally to the above use.

[0094] According to one aspect, the above-described composition for destroying microalgae is applied to marine microalgae culture sites, areas where green or red tides have occurred, or areas where green or red tides are expected to occur, and by inhibiting the growth and proliferation of microalgae, it has the effect of preventing damage from green and red tides.

[0095] The following examples will be explained in more detail. However, these examples are for illustrative purposes only and the scope of the present invention is not limited to these examples.

[0096]

[0097] Preparation Example 1: Synthesis of Vitamin K Derivatives (1) - Compounds 1 and 2

[0098] Compounds 1 and 2, which are vitamin K derivatives, were synthesized through the following process.

[0099] [Reaction Equation 1]

[0100]

[0101] Specifically, 1,4-naphthoquinone (1 eq) and alkylamine (1.2 eq) were added to methanol (0.3 M) and stirred at room temperature for 14 hours. The progress of the reaction was monitored by TLC, and when the reaction ceased, the solvent was removed by vacuum concentration using a rotary vacuum distillation apparatus. The reaction mixture was purified by separating it into a mixed solvent of n-hexane, ethyl acetate, and methanol using silica-packed column chromatography to obtain a solid. The resulting product was recrystallized with ethyl acetate and cold n-hexane to obtain pure red crystals.

[0102]

[0103] Preparation Example 2: Synthesis of Vitamin K derivatives (2) - Compounds 3 to 6

[0104] Compounds 3 to 6, which are vitamin K derivatives, were synthesized through the following process.

[0105] [Reaction Equation 2]

[0106]

[0107] Specifically, 2-methyl-1,4-naphthoquinone (1 eq) and alkylamine (1 eq) were added to methanol (2.3 M) and stirred at room temperature for 4 hours. The progress of the reaction was observed by TLC, and when the reaction ceased, the solvent was removed by vacuum concentration using a rotary vacuum distillation apparatus. The reaction product was purified by separating it into a mixed solvent of dichloromethane and methanol using silica-packed column chromatography, yielding a red solution. Subsequently, the solvent was removed by vacuum concentration using a rotary vacuum distillation apparatus, yielding a red liquid.

[0108]

[0109] Example 1: Chemical formula of a vitamin K derivative and 1 H NMR analysis results

[0110] The chemical formulas of compounds 1 to 6 synthesized in Preparation Examples 1 and 2 above, and 1 The results of the H NMR analysis are listed in the table below. In this specification, the structural formulas of compounds 1 to 6 are each represented by chemical formulas 1 to 6.

[0111]

[0112]

[0113] Compound No. 1H NMR 분석 결과 (300MHz, CDCl3)1δ 8.09(dd, J=7.70, 1.17 Hz 1H), δ 8.04(dd, J=7.64, 1.21 Hz 1H), δ 7.71(td, J=7.56, 1.34 Hz, 1H), δ 7.60(td, J=7.55, 1.32 Hz, 1H), δ 5.70(s, 1H), δ 3.19(q, J=5.71 Hz, 2H),δ 2.61(t, J=6.06 Hz, 2H), δ 2.28(s, 6H)2δ 8.10(dd, J=7.68, 1.30 Hz 1H), δ 8.03(dd, J=7.66, 1.31 Hz 1H), δ 7.71(td, J=7.56, 1.33 Hz, 1H), δ 7.59(td, J=7.54, 1.27 Hz, 1H), δ 5.70(s, 1H), δ 3.27(q, J=5.62 Hz, 2H), δ 2.55(t, J=6.70Hz, 2H), δ 2.35(s, 6H), δ 1.89(quin, J=6.59Hz, 2H)3δ 8.07 (dd, J=7.64, 0.70Hz 1H), δ 7.97(dd, J=7.63, 0.77Hz, 1H), δ 7.66(td, J=7.37, 1.15 Hz, 1H), δ 7.57(td, J=7.54, 1.26 Hz, 1H), δ 3.68(m, 2H), δ 2.62(m, 2H), δ 2.33(s, 6H), δ 2.22(s, 3H)4δ 8.07 (dd, J=7.41, 1.01Hz 1H), δ 7.97(dd, J=7.65, 0.67Hz, 1H), δ 7.65(td, J=7.55, 1.37 Hz, 1H), δ 7.55(td, J=7.54, 1.34 Hz, 1H), δ 3.66(m, , 2H), δ 2.72(dt, J=4.12, 1.01 Hz, 2H), δ 2.61(m, 4H), δ 2.20(s, 3H), δ 1.09(t, J=7.01 Hz, 6H)5δ 8.06 (m, 1H), δ 7.96(m, 1H), δ 7.65(td, J=7.55, 1.38 Hz, 1H), δ 7.54(td, J=7.54, 1.34 Hz, 1H),δ 3.69(t,J=5.83 Hz, 2H), δ 2.49(t,J=6.38 Hz, 2H), δ 2.31(s, 6H), δ 2.19(s, 3H), δ 1.82(m, 2H)6δ 8.06 (m, 1H), δ 7.96(dd, J=7.60, 1.25Hz, 1H), δ 7.64(td, J=7.49, 1.22 Hz, 1H), δ 7.54(m, 1H), δ 3.69(q, J=6.13 Hz, 2H), δ 2.56(m, 6H), δ 2.21(s, 3H), δ 1.77(quin, J=6.39 Hz, 2H), δ 1.05(t, J=7.14 Hz, 6H).

[0114]

[0115] Example 2: Microalgae test species and culture conditions thereof

[0116] In this embodiment, the algal species listed in Table 3 below were used as examples of cyanobacteria (blue-green algae), chlorophyta (green algae), and red tide, respectively, and were obtained from the Freshwater Bioresources Culture Collection (FBCC) of the National Nakdong River Biological Resources Center, the Korea Collection for Type Cultures (KCTC) of the Korea Research Institute of Bioscience and Biotechnology, or the Library of Marine Samples (LIMS) of the Korea Institute of Ocean Science and Technology.

[0117] Classification Algae Species Source Cyanobacteria Microcystis aeruginosa (A59) FBCC Genus Anabaena (Anabaena SP.) (AG10063) KCTC Green Algae Chlorella Vulgaris (AG20696) FBCC Selenastrum Gracile (AG10009) FBCC Red Algae Cochlodinium polykrikoides (PS-3321) LIMS Genus Heterosigma (PS-1653) LIMS

[0118] The above algal species were used by subculturing once every 14 days in 75 cm³ and 200 cm³ SPL cell culture flasks after completely cooling the BG-11 medium prepared using the composition table shown in Table 4 below in a high-temperature, high-pressure sterilizer (15 minutes, 121°C) and then cooling it completely at refrigeration or room temperature. All subculture processes were carried out in a clean bench to prevent contamination. The algae were cultured in a Lab House incubator under the conditions shown in Table 5: a 16:8 cycle (Light:Dark), 2300–2700 Lux, and 20–25°C.

[0119] BG -11 (Blue-Green Medium)Stocks CompoundMedium(per liter)1NaNO315.0 g / L100.0 mL2K3HPO42.0 g / 0.5L10.0 mL each3MgSO 4· 7H2O3.75 g / 0.5L4CaCl 2· 2H201.80 g / 0.5L5Citric acid0.30 g / 0.5L6Ammonium ferric citrate green0.30 g / 0.5L7EDTA Na20.05 g / 0.5L8Na2NO31.00 g / 0.5L9H3BO32.86 g / L1.0 MlMnCl 2· 4H2O1.81 g / LZnSO 4· 7H200.22 g / LNaMoO 4· 2H200 0.39 g / LCuSO4· 5H200.08 g / LCo(NO3) 2· 6H200.05 g / LMake up to liter with deionized water. Adjust pH to 7.1 with 1M NaOH or HCl.For afar add 15.0 g per liter of Vacteriological Agar(Oxoid L11).Autoclave at 15 psi for 15 minutes.

[0120] Culture Conditions Algae Name: Light : Dark Cycle: 16 hours : 8 hours Temperature: 20 to 25 ℃ pH: 7 to 8 Medium: BG-11

[0121]

[0122] Example 3: Evaluation of the algicidal activity of vitamin K derivatives against cyanobacteria and green algae

[0123] To evaluate the algicidal activity of the vitamin K derivatives synthesized in Preparation Examples 1 and 2 above against cyanobacteria and green algae, the following experiment was performed.

[0124] Specifically, after dispensing the cyanobacteria or green algae of Example 2 into a 96-well plate, the six compounds synthesized in the above preparation example were each treated at different concentrations; considering that the color of the cyanobacteria or green algae becomes lighter as the algicidal rate increases, the absorbance was measured at 25°C and 680 nm using a microplate reader 5 days after treatment with the compounds, and the EC 50 The value was derived.

[0125] In addition, the absorbance value representing 100% aerocytic rate was corrected for the absorbance value of each drug, and the aerocytic rate (%) was calculated by measuring the change in absorbance compared to the control group that was not treated with the drug.

[0126] As a result of the above experiment, the six compounds showed high algicidal activity against all four types of microalgae used in the experiment (Table 6), and it was confirmed that they showed high algicidal activity against the harmful cyanobacteria genus Microcystis in particular.

[0127] Compound No. Microcystis Aerugianosa EC 50 (120 h)(μM)Anabaena EC 50 (120 h)(μM)Chlorella EC 50 (120 h)(μM)SelenastrumEC 50 (120 h)(μM)10.20±0.021.07±0.051.36±0.051.82±0.0420.03±0.001.12±0.072.26±0.043.22±0.1130.69±0.031.15±0.041.63±0.042.96±0 .0640.35±0.040.67±0.041.57±0.062.37±0.0450.46±0.020.62±0.021.53±0.072.26±0.0760.33±0.030.62±0.041.74±0.032.68±0.09

[0128]

[0129] Example 4: Evaluation of the algicidal activity of vitamin K derivatives against red algae

[0130] To evaluate the algicidal activity of the vitamin K derivatives synthesized in Preparation Examples 1 and 2 above against red algae, the following experiment was performed.

[0131] Specifically, the red algae of Example 2 was diluted with BG-11 to 300~400X10 4 It was prepared to a cell / mL concentration. To verify the algicidal ability according to compound concentration, compounds were treated at different concentrations in prepared 96-well plates. 100μL (300~400×10⁻⁶) of each algal species was applied. 4100 μL of compounds diluted with BG-11 (cell / mL) and BG-11, for a total of 200 μL, were added to a 96-well plate and left for 1 day under constant culture conditions. After 24 hours, at least 10 μL of each compound was taken at the corresponding concentration and placed on a Neubauer hemocytometer (Superior, Germany). The number of intact algal cells was then confirmed using an electron microscope (Nikon, ECLI-PSE E100, 0.3A, 50–60 Hz). The cell reduction rate and algicidal activity were calculated by substituting the number of cells for each concentration and the number of cells in the control group into the following Equation 1.

[0132] [Mathematical Formula 1]

[0133]

[0134] [T t : Number of cells in treatment group, T C : Number of control cells. t: Number of days after inoculation]

[0135] A concentration (EC) capable of controlling the cell number by 50% compared to the control group 24 hours after inoculation with the compound. 50 - 24h) was calculated using sigmaplot version 12.5 software based on the following mathematical formula 2 for the standard curve, sigmoid, and for parameter logistic curve.

[0136] [Mathematical Formula 2]

[0137]

[0138] [Y : Algaecidal activity according to compound inoculation concentration (%), A : Maximum activity according to inoculation concentration (%), B : Minimum algaecidal activity according to inoculation concentration (%), C : EC50-24h within the inoculation concentration range, D : Hillspope]

[0139] Subsequently, EC for each inoculation concentration obtained based on Mathematical Formula 2 50 The value was error-corrected using the 100% algae activation value.

[0140] As a result of the above experiment, the six compounds showed high algicidal activity against both types of red algae used in the experiment (Table 7), and it was confirmed that they showed high algicidal activity against the harmful red algae, the genus Cochlodinium.

[0141] Compound No. Cochlodinium EC 50 (24 h) (μM)Heterosigma EC 50 (24h) (μM)10.29±0.041.06±0.0720.28±0.031.52±0.0730.18±0.030.85±0.0340.12±0.020.09±0.0050.24±0.020.54±0.0460.39±0.041.38±0.08

[0142]

[0143] Example 5: Evaluation of the toxicity of vitamin K derivatives to water fleas

[0144] In order to evaluate the safety of the vitamin K derivatives synthesized in Preparation Examples 1 and 2 above for aquatic organisms, we sought to determine the toxicity to Daphnia magna, an aquatic invertebrate used in the acute toxicity test of the Standard Test for Water Pollution.

[0145] First, water fleas were cultured under the conditions listed in Table 9 below.

[0146] Photoperiod: 16-hour light conditions (08:00 - 24:00) / 8-hour dark conditions (24:00 - 08:00) Water temperature: 18-22℃ pH: 6.0-9.0 Dissolved oxygen ≥ 3 mg / L Hardness: 140-250 mg / L Food: Chlorella sp.

[0147] In addition, ecotoxicity analysis was performed by referring to the criteria presented in the Water Quality Pollution Standard ES 04704.1b acute toxicity test method for Daphnia, and the detailed test conditions are listed in Table 9 below.

[0148] Classification Actual Test Conditions Test Species: Daphnia magna (Straus) Test Method: Standard Test Methods for Water Pollution ES 04704.1b Exposure Time: 24 hours, 48 ​​hours Test Temperature: 20 ℃ Number of Test Organisms by Concentration: 15.5 Repetitions: 3 times Amount of Test Solution: 50 mL Age of Test Organism: Less than 24 hours Endpoint Marking: EC 50 Light conditions 16 h : 8 h (light: Dark), 800 Lux

[0149] To evaluate toxicity to Daphnia, the Vitamin K derivatives synthesized in Preparation Examples 1 and 2 were treated to each test solution at different concentrations, and the number of Daphnia individuals with inhibited swimming or death was counted after 24 and 48 hours to determine the EC 50 The value (half-influence concentration) was derived.

[0150] As a result of the above experiment, it was confirmed that the six types of compounds did not exhibit toxicity to water fleas or exhibited low toxicity compared to algae (Table 10).

[0151] Compound No. Daphnia magna EC 50 values ​​for compounds (μM)24h48h116.66±0.8310.16±1.01228.75±2.8816.53±1.5433.58±0.312. 79±0.4848.05±0.916.87±0.4955.39±0.352.24±0.2868.30±0.894.40±0.54

[0152]

[0153] Example 6: Evaluation of the toxicity of vitamin K derivatives to zebrafish

[0154] In order to evaluate the safety of the vitamin K derivatives synthesized in Preparation Examples 1 and 2 above for aquatic organisms, we intended to determine the toxicity to the zebrafish (Danio rerio), an animal model that is actively being researched for various diseases because it is similar in size and number to the human body among aquatic organisms.

[0155] First, zebrafish were cultured under the conditions listed in Table 11 below.

[0156] Glass-fronted tank Water temperature 21 - 25 ℃ Photoperiod 16 hours light conditions (08:00 - 24:00) / 8 hours dark conditions (24:00 - 8:00) Dissolved oxygen 80% or higher Illumination 300 - 600 lux Food: Artemia supplied once daily

[0157] In addition, toxicity analysis was performed by referring to the regulations on test methods for chemical substances, National Institute of Environmental Research Notice No. 2020-28, and the detailed test conditions are listed in Table 12 below.

[0158] Classification Actual Test Conditions Test Species: Danio rerio Exposure Time: 24 hours, 48 ​​hours, 72 hours, 96 hours Test Temperature: 23 ℃ Number of Test Organisms by Concentration: 10 individuals Volume of Test Solution: 3 L Total Length of Test Organism: 1 ~ 2 cm Endpoint Marking: EC 50 Light conditions 16 h : 8 h (light: Dark)

[0159] To evaluate toxicity to zebrafish, each test solution was treated with the vitamin K derivatives synthesized in Preparation Examples 1 and 2 at various concentrations. Lethality rates and visible external abnormalities or behavioral signs were recorded at 48 and 96 hours after the start of the experiment, and the concentration that causes lethality to 50% of the fish (LC₀) was determined. 50 ) was derived. Meanwhile, lethality was determined when there was no movement or gill respiration stopped when the fish was touched with a glass rod.

[0160] As a result of the above experiment, it was confirmed that the six compounds exhibited no toxicity to zebrafish or showed low toxicity compared to birds (Table 13).

[0161] Compound No. Danio rerio EC 50values ​​for compounds (μM)48h96h193.99±9.8972.82±6.112133.82±16.5885.1±8.12335.38±2.5419.1 7±1.51438.36±3.2130.39±2.89557.1±6.3429.32±1.99647.74±3.1228.91±3.21

[0162]

[0163] Example 7: Comparative Evaluation of Algaecidal Activity of Vitamin K Derivatives

[0164] To compare and evaluate the algicidal activity of the vitamin K derivatives synthesized in Preparation Examples 1 and 2 above, the following experiment was performed.

[0165]

[0166] 7.1: Comparative Evaluation of Compounds 1 and 2

[0167] To further confirm the algicidal activity of compounds 1 and 2 among the vitamin K derivatives synthesized in Preparation Examples 1 and 2 above, the algicidal activity was evaluated by comparing it with compounds CC-1 and CC-2, which have a similar structure (the alkyl group of the dialkylamino group is an ethyl group).

[0168]

[0169]

[0170] Specifically, based on the methods described in Examples 3 and 4, algicidal activity against Microcystis aruginosa, a representative harmful cyanobacteria, and Heterosigma, a representative red algae, was confirmed.

[0171] As a result of the above experiment, it was confirmed that compounds 1 and 2 exhibited significantly superior algicidal activity compared to compounds CC-1 or CC-2, respectively (Table 15). For Microcystis aruginosa, compound 2 showed approximately 17 times higher algicidal activity compared to the comparative compound CC-2, and for Heterosigma algae, compound 1 showed approximately 5 times higher algicidal activity compared to the comparative compound CC-1.

[0172] Compound No. Microcystis Aerugianosa EC 50 (120 h) (μM)Heterosigma EC 50 (24 h) (μM)10.211±0.011.042±0.0520.027±0.0051.694±0.08CC-10.624±0.015.549±0.38CC-20.458±0.033.136±0.25

[0173]

[0174] 7.2: Comparative evaluation of compounds 3 to 6

[0175] In order to further confirm the algicidal activity and toxicity of compounds 3 to 6 among the vitamin K derivatives synthesized in Preparation Examples 1 and 2 above, the algicidal activity and toxicity were evaluated by comparing them with compounds CC-3 to CC-6, which have a similar structure (in which the methyl group of 1,4-naphthoquinone is substituted with a chloro group).

[0176]

[0177]

[0178] First, based on the method described in Example 3, the algicidal activity against representative harmful cyanobacteria of the genus Anabaena was confirmed, and it was confirmed that compounds 3 to 6 each exhibited significantly superior algicidal activity compared to compounds CC-3 to CC-6 (Table 17).

[0179] Compound No. Anabaena EC 50 (120 h) (μM)31.08±0.0240.75±0.0450.53±0.0260.60±0.03CC-31.61±0.08CC-41.09±0.04CC-51.01±0.04CC-61.25±0.06

[0180] Next, based on the method described in Example 6, the toxicity to zebrafish (Danio rerio) was confirmed, and it was confirmed that compounds 3 to 6 each exhibited significantly lower toxic activity compared to compounds CC-3 to CC-6 (Table 18).

[0181] Compound No. Danio rerio EC 50 values ​​for compounds (μM)48h96h334.24±2.5422.15±1.85439.12±2.4429.89±2.31554.15±6.4525.54±1.85644.23±2.8730.12±2.1 1CC-313.52±1.385.72±0.48CC-427.62±1.5722.12±2.23CC-55.21±0.122.14±0.34CC-615.45±0.988.15±0.99

[0182]

[0183] The foregoing description of the present invention is for illustrative purposes only, and those skilled in the art will understand that other specific forms can be easily modified without altering the technical spirit or essential features of the present invention. Therefore, the embodiments described above should be understood as illustrative in all respects and not restrictive.

[0184]

[0185] The present invention was carried out with the support of the following research project:

[0186] [Project ID] 2480000624

[0187] [Sub-project No.] KE002109

[0188] [Ministry Name] Ministry of Environment

[0189] [Specialized Research Management Agency] Korea Environmental Industry & Technology Institute

[0190] [Research Project Name] Development of Safety Management Technology for Household Chemical Products (Preliminary Feasibility Study)

[0191] [Research Project Title] Development of Glutaraldehyde Substitutes in Algicides

[0192] [Organizing Organization] Q-Ears Co., Ltd.

[0193] [Research Period] 2025.01.01 ~ 2025.12.31

Claims

1. A composition for destroying microalgae comprising a compound represented by the following chemical formula 7, a stereoisomer thereof, a salt thereof, a hydrate thereof, or a solvate thereof: [Chemical Formula 7] In the above chemical formula 7, A1 and A2 are each independently hydrogen, deuterium, and substituted or unsubstituted C1-C 10 Selected from alkyl groups, and A3 is independently hydrogen, deuterium, substituted or unsubstituted C1-C 10 Alkyl groups, substituted or unsubstituted C2-C 10 alkenyl groups, substituted or unsubstituted C2-C 10 alkynyl group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C2-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted C2-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C3-C 10 Aryl groups, and substituted or unsubstituted C2-C 10 Selected from heteroaryl groups, A4 is hydrogen, deuterium, and substituted or unsubstituted C1-C 10 Selected from alkyl groups, and A5 is each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -OH, cyano group, nitro group, amino group, amidino group, substituted or unsubstituted C1-C 10 Alkyl groups, substituted or unsubstituted C2-C 10 alkenyl groups, substituted or unsubstituted C2-C 10 alkynyl group, substituted or unsubstituted C1-C 10 Alkoxy groups, substituted or unsubstituted C3-C 10 Cycloalkyl group, substituted or unsubstituted ternary to 10-membered heterocycloalkyl group, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted ternary to decary heterocycloalkenyl group, substituted or unsubstituted C3-C 10 Aryl group, substituted or unsubstituted C3-C 10 Aryloxy group, substituted or unsubstituted C3-C 10 Selected from an arylthio group and a substituted or unsubstituted 3 to 10-membered heteroaryl group, m is selected from integers 1 to 10, and n is selected from integers 0 to 4.

2. A composition according to claim 1, wherein in the formula 7, A1 and A2 are each independently selected from hydrogen and a substituted or unsubstituted methyl group.

3. A composition according to claim 1, wherein in the formula 7, A3 is selected from hydrogen and a substituted or unsubstituted C1-C5 alkyl group.

4. A composition according to claim 1, wherein in the formula 7, A4 is selected from hydrogen and a substituted or unsubstituted methyl group.

5. A composition according to claim 1, wherein in the formula 7, m is selected from integers 1 to 3.

6. The composition of claim 1, wherein the composition comprises one or more compounds selected from the group consisting of compounds 1 to 6 described below, stereoisomers thereof, salts thereof, hydrates thereof, or solvates thereof: .

7. A composition according to claim 1, wherein the microalgae comprises one or more selected from the group consisting of cyanobacteria, diatoms, green algae, red algae, euglenoid algae, flagellates, yellow-green algae, dinoflagellates, scleroflavinates, and algae capable of producing biodiesel.

8. A composition according to claim 7, wherein the microalgae comprises one or more microalgae selected from the group consisting of Microcystis, Anabaena, Chlorella, Selenastrum, Cochlodinium, and Heterosigma.

9. A composition according to claim 7, wherein the microalgae comprises one or more microalgae selected from the group consisting of Microcystis aeruginosa, the genus Anabaena, Chlorella Vulgaris, Selenastrum Gracile, Cochlodinium polykrikoides, and the genus Heterosigma.

10. A method for destroying microalgae, comprising the step of treating a composition for destroying microalgae according to any one of claims 1 to 9 in a marine microalgae culture facility, an area where green algae or red tide occurs, or an area where green algae or red tide is expected to occur.

11. A composition for water quality improvement comprising a compound represented by the following chemical formula 7, a stereoisomer thereof, a salt thereof, a hydrate thereof, or a solvate thereof: [Chemical Formula 7] In the above chemical formula 7, A1 and A2 are each independently hydrogen, deuterium, and substituted or unsubstituted C1-C 10 Selected from alkyl groups, and A3 is independently hydrogen, deuterium, substituted or unsubstituted C1-C 10 Alkyl groups, substituted or unsubstituted C2-C 10 alkenyl groups, substituted or unsubstituted C2-C 10 alkynyl group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C2-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted C2-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C3-C 10 Aryl groups, and substituted or unsubstituted C2-C 10 Selected from heteroaryl groups, A4 is hydrogen, deuterium, and substituted or unsubstituted C1-C 10 Selected from alkyl groups, and A5 is each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -OH, cyano group, nitro group, amino group, amidino group, substituted or unsubstituted C1-C 10 Alkyl groups, substituted or unsubstituted C2-C 10 alkenyl groups, substituted or unsubstituted C2-C 10 alkynyl group, substituted or unsubstituted C1-C 10 Alkoxy groups, substituted or unsubstituted C3-C 10 Cycloalkyl group, substituted or unsubstituted ternary to 10-membered heterocycloalkyl group, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted ternary to decary heterocycloalkenyl group, substituted or unsubstituted C3-C 10 Aryl group, substituted or unsubstituted C3-C 10 Aryloxy group, substituted or unsubstituted C3-C 10 Selected from an arylthio group and a substituted or unsubstituted 3 to 10-membered heteroaryl group, m is selected from integers 1 to 10, and n is selected from integers 0 to 4.

12. A method for improving water quality comprising the step of treating a marine microalgae culture facility, an area where green or red tide occurs, or an area where green or red tide is expected to occur with the water quality improvement composition of Claim 11.

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