JPH07258006A - Controlling agent for aquatic injurious periphyton - Google Patents

Abstract

PURPOSE:To obtain the sect highly safe controlling agent containing, as active ingredient, (2R,5R,10R)-2-formamido-6-axeen derived from, e.g. natural-occurring sponge. CONSTITUTION:This controlling agent for aquatic injurious periphyton contains, as active ingredient, (2R,5R,10R)-2-formamido-6-axeen of the formula derived from, e.g. Oxeosarcodea-oinops, a kind of sponge, through its extraction and purification. For this controlling agent, the compound of the formula can be used either singly or in combination with other controlling agent(s). This controlling agent can be used in the form of coating, solution, or emulsion, being excellent in the repelling effect on injurious marine organisms and safe to the human body and environment while maintaining effects at least comparable to those with the case of controlling methods using conventional heavy metal compounds.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to the bottom of ships, fishing nets for aquaculture and stationary, equipment placed in the sea such as buoys, condenser cooling water for nuclear power and thermal power plants, or heat exchanger cooling for the petrochemical industry. The present invention relates to an agent for controlling harmful organisms in the water, which prevents harmful marine organisms from adhering to and multiplying intake channels for water.

[0002]

2. Description of the Prior Art Barnacles, oysters, mussels, hydras, serpras, squirts, etc.
Shellfish and algae such as bryozoans, sea lettuce, sea bream, and green algae attach and grow. These organisms cause an increase in fluid resistance by attaching to the bottom of ships, resulting in loss of fuel. Further, if it adheres to the cooling equipment part, it causes a decrease in thermal conductivity, which reduces the capacity of equipment and the like, which causes great economic damage.

Conventionally, various control agents have been used in order to prevent such adhesion and overgrowth of marine pests. As active ingredients of such control agents, cuprous oxide, organotin compounds and the like are known and are still widely used. These active ingredients are contained in the paint in an amount of 10 to 50% by weight, and the active ingredients are applied to the bottom of a ship or the like and continuously eluted in seawater to prevent the attachment of pests.

[0004]

Recently, the environment such as rivers and seawater is polluted by heavy metals and harmful elements, and since it is a persistent compound or a highly accumulating compound, it is a compound of the human body mediated by seafood. Since there is a risk of damage to health, guidance is currently being given on the use of the most frequently used organotin compounds. Therefore, there is an urgent need for the development of safe and effective active ingredients that replace conventional control agents.

[0005]

[Means for Solving the Problems] In view of such a current situation,
The present inventors have conducted extensive studies to develop a compound having a high safety and excellent control effect, (2R, 5R, 10R) -2-
The present inventors have found that formamide-6-accen has a controlling effect on harmful marine periphytic organisms, and have completed the present invention based on this finding.

That is, the present invention is represented by the formula (I).
(2R, 5R, 10R) -2-Formamide-6-Acene is an agent for controlling harmful organisms in water, characterized by containing as an active ingredient.

[0007]

[Chemical 2]

(2R, 5R, 10R) -2-formamide-6-accene is a known compound (H. He, DJ Faulkner, J.
S. Shunsky, K. Hong, and J. Claudy, J. Org Chem. ,
54,2511-2514 (1989)), for example, a kind of sponge
Obtained by extracting and purifying from Oxeosarcodea oinops . The extraction solvent used here is generally an organic solvent, preferably acetone or ethanol. As the purification method, known methods such as partition purification and chromatography can be used, but silica gel chromatography using a mixed solvent of hexane and chloroform as an eluent is preferably used. Further, not only the above-mentioned method of extracting from an organism but also chemical synthesis is possible.

Used as an active ingredient in the present invention (2
R, 5R, 10R) -2-Formamido-6-accene may be used alone or in combination with other controlling agents. The control agent of the present invention is used by being prepared in the form of paint, solution, emulsion and the like, and these preparations can be carried out without any problem by adopting a commonly used general formulation. For example, when used as a paint, the above-mentioned active ingredient can be mixed with a paint composition to prepare an antifouling paint, which can be applied to the bottom of the ship, the undersea structure and the cooling water intake passage. The antifouling paint is prepared by mixing the active ingredient, a film-forming agent, and a general solvent, extender pigment, coloring pigment, and additive as desired. As the coating film forming agent used at this time, for example, chlorinated rubber resin, vinyl acetate resin, acrylic resin,
Examples include natural resins. In this case, the active ingredient is blended in a proportion of 1 to 45%, preferably 5 to 20% based on the weight of the coating material.

When the control agent of the present invention is used as a solution, for example, the active ingredient is mixed with a film-forming agent and dissolved in a solvent to prepare a solution, which is used for the purpose of preventing the adhesion and growth of marine organisms. , Can be applied to stationary fishing nets. The coating film forming agent used at this time includes, for example, chlorinated rubber resin, vinyl acetate resin, acrylic resin, natural resin and the like, and the solvent includes toluene, xylene, cumene, methyl isobutyl ketone and the like. In addition, an additive such as a plasticizer can be added to the solution if necessary. When used as a solution, the active ingredient is 2-40% by weight, preferably 5-20% by weight, based on the weight of the solution.
It is mixed in the ratio of.

When used as an emulsion, the active ingredient is dissolved in a solvent, and a surfactant is further added to prepare an emulsion by a conventional method. As the surface active agent, a generally used one can be used. When used as an emulsion, the active ingredient is incorporated in an amount of 5 to 50% by weight, preferably 10 to 20% by weight, based on the weight of the emulsion. The control agent of the present invention can also be used by kneading it into a polymeric resin material such as a fishing net or a material for undersea use such as concrete.

[0012]

The present invention will be described in detail below with reference to examples, but the scope of the present invention is not limited to these examples. (Example 1) Squid ( Oxeosarcod ) collected in Palau
500 g of ea oinops ) was shredded, 500 ml of acetone was added, and the components were extracted at room temperature. The extract was filtered to remove the residue, and the filtrate was concentrated under reduced pressure at room temperature to remove acetone. To this, 250 ml of ethyl acetate and 250 ml of water were added and distributed,
The upper layer, ethyl acetate, was separated and distilled off at room temperature under reduced pressure to obtain 3.6 g of an oily substance. This oily substance was subjected to silica gel column chromatography (eluent: a mixture of chloroform and hexane 1: 9) to obtain 8 mg of colorless crystals of (2R, 5R, 10R) -2-formamide-6-accene. .

The (2R, 5R, 10R) -2-formamide-6-accen was tested for its adhesion-inhibiting effect using the most important adherent organism, Tatemima barnacles larvae. That is, 0.005 mg of the test compound was dissolved in 0.1 ml of methanol, and the solution was uniformly applied to a circular petri dish having a diameter of 4 cm, and then the methanol was dried. Each of them was placed in a dark place at 23 ° C. After 24 hours, it was taken out, and the number of barnacles that had adhered and transformed on the bottom surface of the petri dish was examined to determine the effect of preventing adhesion.

A similar test was conducted using 0.0125 mg of copper sulfate as a comparative example. The test was repeated 3 times and the average was obtained. The results are shown in Table 1.

[0015]

[Table 1] ──────────────────────────────────── Compound name Barnacle adhesion rate (%) ── ────────────────────────────────── (2R, 5R, 10R) -2-Formamide-6-Acene 0 Copper sulfate 0 Untreated 85 ─────────────────────────────────────

[0016]

Example 2 An example of prescription when the control agent of the present invention is used as an antifouling paint is shown below.

[0017]

[Table 2] ───────────────────────── Composition weight% ───────────────── ───────── (2R, 5R, 10R) -2-Formamide-6-Acene 15 Rosin WW 6 VYHH (Vinyl synthetic resin) 6 Tricresyl phosphate 2 talc 15 Barium sulfate 15 Barley 10 Xylene 26 Methyl isobutyl ketone 5 ───────────────────────── Total 100 ────────────────── ────────

[0018]

EFFECTS OF THE INVENTION The control agent of the present invention was found to be excellent in the effect of repelling harmful organisms adhering to marine organisms, and the use of this control agent has the same or higher effect as the conventional control method using a heavy metal compound, while suppressing the effects on human bodies And environmentally safe control technology is provided.

Claims (1)

[Claims] 1. (2R, 5R, 10R) -2-Formamide-6-Acene [(2R, 5R, 10R) -2-formamido-axe represented by the formula (I)
ne] as an active ingredient. [Chemical 1]