KR100314105B1 - Antifouling coating composition and protection method of structure using the same - Google Patents

Abstract

Certain compounds have been described as useful as seawater or freshwater antifouling compounds for use in protective carrier compositions such as encapsulating polymers to protect fishing nets, boats, piles, and breakwaters. The compound is selected from compounds of the general formula (1, 2, 3, 4, 5, 6, 7, 8, 9).

Description

Antifouling coating composition and method for protecting structure using same

Background of the Invention

The present invention generally relates to the protection of underwater surfaces from contamination by aquatic organisms. The present invention has been approved by the Office of Naval Research (ONR) under Contract No. N00014-86-K-0261 with government support. The government has certain rights in the invention.

Description of the Prior Art

In seawater, brine and freshwater environments, organisms collect, settle, attach and grow on underwater structures. Such organisms may include algae and aquatic animals, such as encapsulates, hydroworms, bivalve shells, moss worms, polypods, sponges and shellfish. Underwater structures may include ships, docks and breakwaters, piles, fishing nets, heat exchangers, dams, pipe structures such as inlet screens, and underwater surfaces of cooling towers. The presence of these organisms, known as "contamination" of the construct, can be detrimental in many respects. They can add weight to the structure and harm its hydraulics, reduce its operating efficiency, increase the likelihood of corrosion, deteriorate the structure or, in severe cases, destroy it.

Conventional methods for inhibiting the attachment of contaminating organisms are to protect the structure with paints or coatings containing antifouling agents. Examples of antifouling coatings and paints are described in US Pat. No. 4,596,724 to Rayne, 4,410,642 to Rayton, and 4,788, 302 to Costlow. Coating of this type of coating neutralizes the organisms or creates an environment that they dislike on the places where they settle, thereby inhibiting the attachment or "settlement" of the organisms.

Among the contaminating organisms described above, clamshells have proven to be one of the most difficult to inhibit. Typically, commercial antifouling coatings and paints include toxic metal containing compounds such as tri-n-butyl tin (TBT), or cuprous oxide, which leaches from the coating. Although these compounds have a moderate effect on inhibiting the settlement of shellfish, they slowly degrade the marine environment and are therefore ecologically harmful. In fact, TBT is so toxic that some countries regulate their release rates by law.

Several experimental non-toxic compounds have been tested to have a limited effect on the inhibition of shellfish settling. For example, Gerhart et al. Describe the use of extracts produced by fucalides, epoxyfucalides, and octocoral Leptogorgia virgulata to inhibit clam shell settlement. , J. Chem. Ecol. 14: 1905-1917 (1988), which describes the use of ethyl acetate extract of sponges Lissodendoryx isodictylais to inhibit settlement [Sears et al., J. Chem, Ecol. 16: 791-799 (1990).

Japanese Patent Publication No. 54-44018 (Patent Application No. 52-109110 of September 10, 1977) on April 7, 1979 has a gamma-methylenebutenoid lactone and alkylgamma-methylene having the following general formula: Butenolide lactone derivatives are described.

Wherein R ₁ and R ₂ are hydrogen or a saturated or unsaturated alkyl group having 1 to 8 carbon atoms. This compound is a natural product from land plants.

Summary of the Invention

In view of the above, it is an object of the present invention to provide an antifouling composition effective for inhibiting the settlement of contaminating organisms on the surface of water.

Another object of the present invention is to provide an antifouling paint or coating composition effective to protect underwater structures from contamination by clamshells, and other aquatic organisms.

Another object is to provide a structure that is effectively protected from contamination by aquatic organisms.

These and other objects are, in one embodiment, intended for use as a seawater or freshwater antifouling agent comprising a protective carrier component which acts to release an antifouling agent, and at least one compound selected from the group consisting of the following compounds as antifouling agents. Achieved by the composition.

Wherein R ₁ , R ₂ , R ₃ and R ₄ are -C (0) R ₅ , -C (0) OR ₆ , (C ₁ -C ₈ ) alkyl, phenyl, (C ₁ -C ₄ ) alkyl Is independently selected from phenyl substituted with (C ₁ -C ₄ ) alkoxy, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl, halogen, and hydrogen, provided that R ₁ , R At least one of ₂ , R ₃ and R ₄ is not hydrogen;

R ₅ is R ₆ or NR ₇ R ₈ ;

R ₆ is (C ₁ -C ₈ ) alkyl, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl, phenyl, phenyl substituted with (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy or halogen;

R ₇ and R ₈ are independently selected from hydrogen or R ₆ ;

R ₉ , R ₁₀ , R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₁₇ , R ₁₈ , R ₁₉ , R ₂₀ and R ₂₁ are hydrogen and (C ₁ -C ₁₀ ) alkyl Independently selected from the group consisting of;

R ₂₂ , R ₂₃ and R ₂₄ are each independently selected from hydrogen, a (C ₁ -C ₃ ) alkyl group, a (C ₁ -C ₃ ) alkoxy group, a halogen and a hydroxy group.

A second aspect of the invention consists in a method for protecting a seawater or freshwater structure from contamination by seawater or freshwater contaminating organisms, which consists in applying one or more of the compounds onto and / or in the structure.

Another aspect of the invention relates to seawater or freshwater structures protected from contaminating organisms, wherein the protection is achieved by applying one or more of the compounds onto and / or inside the structure.

1 is a graph showing the settling rate of an untreated control sample as a function of larval density. The least squares regression equation for the data is Y = 47.4 (log X)-41.3, where Y is the settling rate and X is the larval density.

2 is a graph showing the settling rate of treated samples as a function of larval density. The least squares regression equation for the data is Y = -51.7 (log X) + 118.6, where Y is the settling rate and X is the larval density.

The present invention is intended to suppress the attachment of unwanted organisms to the surface of water by contacting an organism with at least one compound having antifouling activity selected from the group consisting of the general formulas (1) to (9).

These compounds have been found to inhibit the settling of contaminating organisms, especially clam stalks. As used herein, "settlement" means that an underwater organism is attached to an underwater structure. By contacting the organism with a compound of the present invention in an area adjacent to the underwater surface, the settlement of the organism on the underwater surface is prevented.

In the practice of the method of the present invention, the antifouling compound is applied to the object to be protected with a coating containing the antifouling compound and then the compound is released into the aquatic environment immediately adjacent to the outer surface of the article, or the antifouling compound is an underwater article Release the compound after inclusion in the material formed therein, directly into the aquatic environment around the object to be protected, or by any other method of contacting the compound with the organism before the organism adheres to the surface. Can be contacted. As used herein, "contact" refers to physical contact of an organism with an amount of an antifouling compound sufficient to inhibit the establishment of the organism on the surface of the subject by direct external contact, inhalation, respiration, digestion, repression, or other means. Means that.

Preferred compounds are 2-ethylfuran; 2-methylfuran; Methyl-2-furanoate; Ethyl-3-furoate; 2-furyl-n-pentyl ketone; 2-acetylfuran; Keline; γ-dekaralactone; α-angelica lactone; α-santonin; α-methylene-γ-butyrolactone; Coumaranone; Allantolactone; And 3-methyl-2-cyclohexen-1-one.

The amount of compound used in the method of the present invention will depend on many factors, including the type of antifouling compound, the type of organism to be inhibited, and the mode of contact. In addition, the rate at which the compound is released into the surrounding aquatic environment can be a major factor in determining both the efficiency of the process and the duration of protection. If the compound is released too quickly, it will be quickly consumed and the coating must be reapplied to protect the surface. On the other hand, if the release rate of the antifouling compound is too slow, the concentration of the compound in the aquatic environment immediately around the surface to be protected may be insufficient to inhibit fixation. Preferably, the antifouling compound is released into the environment adjacent to the surface to be protected at a rate of about 0.0001 to 1000 g / cm 2 time, more preferably about 0.01 to 100 g / cm 2 time. The composition of the present invention preferably contains at least one compound of the present invention at a concentration of from about 0.01% to about 50% by weight, more preferably from about 0.1 to 20% by weight, based on the composition.

The organisms whose surfaces can be protected against them by the method of the invention are any organisms that can be attached to the surface underwater. Examples of organisms include algae, including members of the Chlorophyll statement, and seaweeds such as fungi, bacteria, Ciona intestinalis, Diplosoma listerianium, Botryllus sclosseri Members of the river, including Clava squamata, Hydractinia echinata, Obelia geniculata, and Tubularia larnyx. Encapsulations, including Mytilus edulis, Crassostrea virginica, Austrian edulis, Austrian estrea chilensia, and Lasaea lubra bivalve including rubra, mossy worm including Extra pilosa, Bugula neritinia, Bowerbankia gracilis, Hydroids norvegica, sponges, and Balanus amphitrite, Lepas anatifera, Balanus balanus, Balanus balanoids balanoides, Balanus hameri, Balanus crenatus, Balanus improvisus, Balanus galeatus, and Balanus eburneus There are members of the shellfish (shell hat). Organisms in the genus Balanus are a particularly frequent contaminant of underwater structures. Particular contaminant organisms of particular relevance directly to the present invention are clam hatts, zebra tribes, algae, bacteria, diatoms, hydroworms, moss bugs, sea squirts, tubular worms, and Asian clams.

In addition to the compounds of the present invention, the composition may comprise further antifouling agents which may act in combination or synergistically, such further antifouling agents include, for example, manganese ethylene bisdithiocarbamate; Coordination products of zinc ions and manganese ethylene bisdithiocarbamate, zinc ethylene bisdithiocarbamate; Zinc dimethyl dithio carbamate; 2,4,5,6-tetrachloroisophthalonitrile; 2-methylthio-4-t-butylamino-6-cyclopropylamino-s-triazine; 3- (3,4-dichlorophenyl) -1,1-dimethylurea; N- (fluorodichloromethylthio) -phthalimide; N, N-dimethyl-N'-phenyl- (N-fluorodichloromethylthio) -sulfamide; Tetramethylthiuram disulfide; 2,4,6-trichlorophenyl maleimide; Zinc 2-pyridinethiol-1-oxide; Copper thiocyanate; Cu 10% Ni alloy solid solution; And 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one.

The protective carrier component that functions to release the antifouling agent may be a film forming component, an elastomer component, a cured rubber, or a cement component. The protective carrier component may be a component or combination of components that is readily applied to the surface to be protected, adheres to the underwater surface to be protected and releases the antifouling compound into the water immediately around the applied surface. Different components will be desirable depending on the material constituting the underwater surface, the requirements of the action of the surface, the shape of the surface, and the antifouling compound. An example of the film forming component is a polymer resin solution. Examples of polymer resins include (a) unsaturated and anhydrides such as maleic anhydride, fumaric acid, and itaconic acid, (b) phthalic anhydride, isophthalic anhydride, terephthalic anhydride, tetrahydrophthalic anhydride, tetrahalophthalic anhydride, chloride Saturated acids and anhydrides such as acids, adipic acid and sepamic acid, (c) ethylene glycol, 1,2-propylene glycol, dibromoneopentyl glycol, Dianol 33®, and dianol 22 And unsaturated polyester resins formed from vinyl monomers such as (d) styrene, vinyl toluene, chlorostyrene, bromostyrene, methyl methacrylate and ethylene glycol dimethacrylate. Other suitable resins include vinyl ester-, vinyl acetate- and vinyl chloride-based resins, elastomer components, cured rubbers and urethane based resins. Cement compounds are used to protect certain types of underwater structures, as well as elastomeric materials and cured rubbers.

The percentage of the antifouling compounds of the present invention in the coating necessary to adequately release the compounds into the aquatic environment around the surface to be protected is present in the coating which may affect the type of antifouling compound, the film forming components of the coating, and the release rate. It will vary depending on the type of other additives being used. As mentioned above, the release rate of the antifouling compound can be a major factor in determining the efficiency of the process of the present invention and the duration of protection. The coating is preferably released into the surrounding water at a rate of about 0.0001 to 1,000 μg / cm 2 time, more preferably about 0.01 to 100 μg / cm 2 time. Preferably, the antifouling compound comprises about 0.001 to 80% by weight of the coating, more preferably 0.01 to 20% by weight of the coating.

Those skilled in the art will appreciate that the coatings of the present invention may take various forms, including paints, gelcoats, varnishes, and the like. The coating may contain, in addition to the antifouling coating and film forming components, components which impart the desired properties such as hardness, strength, stiffness, reduction resistance, impermeability, or water resistance.

The present invention includes an article having a surface coated with a coating containing at least one such compound. Particularly suitable articles for protection by coating are those which are intentionally or accidentally immersed in water for the minimum amount of time necessary to settle the organism on the underwater object. The coated article may include materials known to attach to aqueous organisms such as metals, wood, concrete, polymers, and stones. Examples of articles that may require anti-pollution protection include recreational equipment such as boats and boat hulls, fishing nets, surfboards, jet skis, and water skiing, breakwater and piles, buoys, offshore oil drilling equipment, and decorative or functional stone structures. This includes.

The composition of the present invention may be a cement composition containing at least one of the above antifouling compounds and a cement matrix. Such compositions are suitable for use in underwater structures such as breakwaters, piles, and offshore oil drilling equipment and scaffolds where contaminating organisms tend to settle. Examples of cement matrix compositions are Portland cement and calcium aluminate based compositions. As will be appreciated by those skilled in the art, the cement matrix should be capable of releasing antifouling compounds, and the antifouling compounds should be at a concentration sufficient to inhibit the release rate of the compound from the composition onto the underwater surface of the article formed from the composition. Must exist.

The present invention will now be described in more detail with reference to the following examples, which are intended to provide information to those skilled in the art more fully, but do not limit the invention.

Collection and Cultivation of Experimental Samples

Acorn clam Satan Balanus Ampitrit Darwin's growing individuals were collected from the Duke University Marine Laboratory breakwater in Beaufort, North Carolina. The collected samples were ground and the Nauplius stage larvae released therefrom were described in Rittschof et al., 1. Exp. Mar. Biol. Ecol, 82: 131-146 (1984)] was incubated in the ciprid stage for sifried stage analysis according to the method.

Settlement Analysis for Cyprid Larvae

Settling assays are described in Rittschof et al. J. Chem. Ecol. 11: 551-563 (1985). Three day old Cyprid larvae were used.

All compounds were tested for their ability to inhibit settling by Cyprid larvae of clam Satalan Balanus amphibit. The larvae were added to a 50 × 9 mm polystyrene Petry dish containing 5 ml of emulsified seawater passed through a 100 kDa cut-off filter and varying concentrations of test compounds. The control consisted of clam larvae and filtered seawater added to a dish without test compound. The dish was then irradiated for 20 to 24 hours at 28 ° C. for about 9 hours in the dark for about 15 hours with light irradiation. The dish was then removed from the incubator and examined under a dissecting microscope to determine the survival of the larvae. The larvae were then killed by adding a few drops of 10% formalin solution. The settling rate was quantified as the number of larvae attached to the surface of the dish and expressed as a percentage of the total larvae in the dish. The experiment was performed twice. The lower the percentage of fixation, the more efficient the test compound.

Example 1

Ethyl-3-furoate (9.63 μl) was diluted in 20 ml of seawater. An aliquot of this stock solution was added to a separate dish containing sea water to provide the concentrations shown in Table 1. Larvae were added and the test performed as described above.

Example 2

Methyl-2-furoate (8.48 μl) was diluted in 20 mL of seawater. An aliquot of this stock solution was added to a separate dish containing sea water to provide the concentrations shown in Table 2. Larvae were added and the test performed as described above.

Example 3

2-ethylfuran (6.94 μl) was diluted in 20 mL of sea water. An aliquot of this stock solution was added to a separate dish containing sea water to provide the concentrations shown in Table 3. Larvae were added and the test performed as described above.

Example 4

2-methylfuran (10.98 μl) was diluted in 20 mL of seawater. An aliquot of this stock solution was added to a separate dish containing sea water to provide the concentrations shown in Table 4. Larvae were added and the test performed as described above.

Example 5

2-acetylfuran (9.11 μl) was diluted in 20 mL of seawater. An aliquot of this stock solution was added to a separate dish containing sea water to provide the concentrations shown in Table 5. Larvae were added and tested as described above.

Example 6

2-furyl-n-pentyl ketone (0.909 μl) was diluted in 20 mL of seawater. An aliquot of this stock solution was added to a separate dish containing sea water to provide the concentrations shown in Table 6. Larvae were added and the test performed as described above.

Example 7

2-furyl-n-pentyl ketone (0.909 μl), 2-ethylfuran (6.94 μl) and 2-acetylfuran (9.11 μl) were each diluted in 20 mL of seawater. An aliquot of this stock solution was added to a separate dish containing sea water so that each test substance was provided at a concentration of 500 μg / ml. Larvae were added and the test performed as described above. These data are shown in Table 7.

Example 8

Multiple lactones were tested for inhibition of clam hatch settlement. All lactones were tested at concentrations of 3 × 10 ⁻⁶ M in dishes containing sea water. Larvae were added and the test performed as described above. These data are shown in Table 8.

Example 9

A solution of α-methylene-γ-butyrolactone was prepared in seawater at the concentrations shown in the table below. 5 ml of each solution was added to a pair of dishes. Larvae were then added to the dish and the test was carried out as described above. These data are shown in Table 9.

Example 10

A second test was performed with α-methylene-γ-butyrolactone. A series of α-methylene-γ-butyrolactone solutions were prepared in seawater at concentrations ranging from 500 μg / ml to 50 ng / ml. Aliquots of these solutions were taken and added to a pair of dishes. The actual concentrations tested are shown in the table below. Larvae were then added to the dish and the test was carried out as described above. These data are shown in Table 10.

Example 11

A solution of α-angelica lactone was prepared in seawater at the concentrations shown in the table below. 5 ml of each solution was added to a pair of dishes. Larvae were then added to the dish and the test was carried out as described above. These data are shown in Table 11.

Example 12

A second test was performed with α-angelica lactone. A series of α-angelica lactone solutions were prepared in seawater at concentrations ranging from 500 μg / ml to 5 ng / ml. Aliquots of these solutions were taken and added to a pair of dishes. The actual concentrations tested are shown in the table below. Larvae were then added to the dish and the test was carried out as described above. These data are shown in Table 12.

Example 13

A 2-coumaranon solution (25 [mu] g in 50 ml of filtered seawater) was prepared. An aliquot of this solution was taken and added to a pair of dishes to provide the nominal concentrations shown in the table below. Larvae were then added to the dish and the test was carried out as described above. These data are shown in Table 13.

Example 14

A series of γ-dekaralactone solutions were prepared in seawater at concentrations ranging from 500 μg / ml to 5 pg / ml. Aliquots of these solutions were taken and added to a pair of dishes. The actual concentrations tested are shown in the table below. Larvae were then added to the dish and the test was carried out as described above. These data are shown in Table 14.

Example 15

A series of γ-valerolactone solutions were prepared in seawater at concentrations ranging from 500 μg / ml to 500 pg / ml. Aliquots of these solutions were taken and added to a pair of dishes. The actual concentrations tested are shown in the table below. Larvae were then added to the dish and the test was carried out as described above. These data are shown in Table 15.

Example 16

Toxicity analysis was performed by adding Nauplius stage larvae to a 50 × 5 mm polystyrene Petri dish or glass vial containing 5 ml of 100 kDa filtered seawater. Dosages of [gamma] -dekaralactone, [alpha] -angelica lactone, [alpha] -methylene- [gamma] -butyrolactone, [alpha] -santonin and allantolactone were placed in the test dish. Dishes or vials without test compound were used as controls. The dish or vial was incubated at 28 ° C. with a 15: 9 light irradiation: dark cycle. After incubation, dishes or vials were examined under a dissecting microscope to determine the survival of the larvae. Larvae that did not respond to visible light emission were considered lethal. The number of surviving larvae and lethal larvae was then counted. Probit analysis was used to obtain concentrations corresponding to half-maximal inhibition (EC ₅₀ value).

These data are summarized in Table 16.

Example 17

Settlement Analysis Process

Laboratory experiments are described in Rittschof et al., J. Exp. Marine Biol. & Ecol. 82: 131-146 (1984), as a three-day-old Cyprid larvae of acorn clam Sagat Balanus amphibitrie. Settling experiments are described in Rittschof et al., J, Chem. Ecol. 11: 551-563 (1985) and Sears et al., J. Chem. Ecol. 16: 791-799 (1990)], using a polystyrene dish. The larvae were added to a polystyrene dish containing 5 ml of emulsified seawater passed through a 100 kilodalton cut-off filter and varying the concentration of 3-methyl-2-cyclohexen-1-one. The control consisted of clam larvae and filtered seawater added to a polystyrene dish free of 3-methyl-2-cyclohexen-1-one. After the larvae were added, the dishes were incubated at 28 ° C. for 20 to 24 hours with a 15: 9 light irradiation: dark cycle.

The dish was then removed from the incubator and examined under a dissecting microscope to determine whether the larvae survived (moved) or died (not moved). The larvae were then killed by the addition of 10% formalin solution drops.

The settling rate was quantified as the number of larvae attached to the surface of the dish and expressed as a percentage of the total larvae in the dish. Dishes containing more than 200 larvae were excluded from subsequent analysis, because too high larval densities could inhibit the settling rate. Linear regression was performed using the log of larval density (larvae per plate) as the dependent variable (Y) and percentage of settling as independent variable. Each dish was treated with a single point.

Settlement Analysis Results

Data was collected for all control dishes (collected data set n = 65). For control, clam moth settlement increased as a linear function of larval density (FIG. 1). The least squares regression equation for the data is Y = 47.4 (log X)-41.3, where Y is the settling rate and X is the larval density. Materials were also collected for the treatments performed by adding 3-methyl-2-cyclohexen-1-one at concentrations of 9, 90 and 900 picomols (collected data set n = 44). At these concentrations, clam hattle settlement decreased as a linear function of clam hat density (Figure 2). The least squares regression equation for the data set is Y = -51.7 (log X) + 118.6, where Y is the settling rate and X is the larval density.

In addition, data were collected for all high concentrations of 3-methyl-2-cyclohexen-1-one (collected data set n = 107: data not shown). The regression line for these points was little different from that of the untreated control (regression equation: Y = 48.5 (log X)-49.1, where Y is the settling rate and X is the larval density). Decreased efficiency at higher concentrations is common for semi-grouped pheromones.

While the invention has been described with reference to specific examples and applications, other variations and uses of the invention will be apparent to those skilled in the art without departing from the spirit and scope of the invention as defined in the following claims.

Claims (13)

At least one selected from the group consisting of a film-forming polymer, a cement material, an elastomer material, and a cured rubber, and a compound selected from the group consisting of an amount effective to be mixed with the material and released from the material at an antifouling effect level. Seawater or freshwater pollution prevention composition comprising an antifouling agent selected from the group consisting of one compound. Wherein R ₁ , R ₂ , R ₃ and R ₄ are -C (0) R ₅ , -C (0) OR ₆ , (C ₁ -C ₈ ) alkyl, phenyl, (C ₁ -C ₄ ) alkyl Are independently selected from phenyl substituted with (C ₁ -C ₄ ) alkoxy, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl, halogen, and hydrogen, provided that R ₁ , R At least one of ₂ , R ₃ and R ₄ is not hydrogen; R ₅ is R ₆ or NR ₇ R ₈ ; R ₆ is (C ₁ -C ₈ ) alkyl, (C ₂ -C ₈ ) alkenyl, (C ₂ -C ₈ ) alkynyl, phenyl, phenyl substituted with (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy, or halogen; R ₇ and R ₈ are independently selected from hydrogen or R ₆ ; R ₉ , R ₁₀ , R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₁₇ , R ₁₈ , R ₁₉ , R ₂₀ and R ₂₁ are hydrogen and (C ₁ -C ₁₀ ) alkyl Independently selected from the group consisting of; R ₂₂ , R ₂₃ and R ₂₄ are each independently selected from hydrogen, a (C ₁ -C ₃ ) alkyl group, a (C ₁ -C ₃ ) alkoxy group, a halogen, and a hydroxy group. The composition of claim 1, wherein the compound is present at a concentration of 0.01% to 50% by weight based on the composition. The composition of claim 2, wherein the compound is present at a concentration of 0.1% to 20% by weight based on the composition. The compound of claim 1, wherein the compound is 2-furyl-methylketone; 2-ethylfuran: 2-methylfuran; Methyl-2-furanoate; Ethyl-3-furoate; 2-furyl-n-pentyl ketone; 2-acetylfuran; Keline; γ-dekaralactone; α-angelica lactone; α-santonin; α-methylene-γ-butyrolactone; Coumaranone; Allantolactone; And 3-methyl-2-cyclohexen-1-one. The composition of claim 1 further comprising at least one antifouling agent. 6. The method of claim 5, wherein said additional antifouling agent is selected from manganese ethylene bisdithiocarbamate; Coordination products of zinc ions and manganese ethylene bisdithiocarbamate; Zinc ethylene bisdithiocarbamate; Zinc dimethyl dithiocarbamate; 2,4,5,6-tetrachloro-isophthalonitrile; 2-methylthio-4-t-butylamino-6-cyclopropylamino-s-triazine; 3- (3,4-dichlorophenyl) -1,1-dimethylurea; N- (fluorodichloromethylthio) -phthalimide; N, N-dimethyl-N'-phenyl- (N-fluorodichloromethylthio) -sulfamide; Tetramethylthiuram disulfide; 2,4,6-trichlorophenyl maleimide; Zinc 2-pyridinethiol-1-oxide; Copper thiocyanate; Cu 10% Ni alloy solid solution; And 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one. A method of protecting a structure from contamination by seawater or freshwater contaminating organisms, comprising applying the composition according to claim 1 on or in a structure, or on and in the structure. 8. The method of claim 7, wherein said seawater or freshwater contaminating organism is selected from the group consisting of clam hatts, zebra tribes, algae, bacteria, diatoms, hydroworms, moss bugs, tubular worms, and Asian clams. 8. The method of claim 7, wherein said organism is one or more organisms of the genus Balanus. 8. The method of claim 7, wherein said compound is used in a composition comprising a film-forming polymer binder. Seawater or freshwater structures which are protected from contaminating organisms by the method according to claim 7. 12. The seawater or freshwater structure of claim 11, wherein said protection is protected by a composition consisting of a film-forming polymer binder containing at least one furan compound applied on or within the structure, or on and within the structure. . The seawater or freshwater structure according to claim 11, wherein the structure is a fishing net, boat, pile, or breakwater, or a cooling tower.