JPS6242904B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention provides novel and useful N-substituted-4-phenylthiazolin-2-one compounds and the novel N-substituted-4-phenylthiazolin-2-one compounds.
The present invention relates to an aquatic organism repellent containing a ion compound as an active ingredient. At all times, such as the bottom of ships, fishing nets, buoys, and other underwater structures, underwater structures such as dam equipment, condenser cooling water in thermal power plants, heat exchanger cooling water intake channels in various industries, etc. On parts that come into contact with water, shellfish such as potholes, oysters, mussels, hydrobugs, serpura, bryozoans, sea squirts, sea lettuce, blue seaweed, and seaweed, as well as algae, adhere to and propagate on parts that come into contact with water. deceleration,
This not only causes an increase in fuel consumption, but also economic losses due to cleaning costs for cleaning the bottom of the ship or suspension of ship operations during this cleaning period. In addition, the amount of water taken into the intake channels for condensers, heat exchangers, etc. will decrease, which will not only reduce the cooling efficiency but also cause biomass that have fallen off the channel walls and been washed away. As a result, it causes major losses such as deterioration of the performance of equipment. Therefore, heavy metal compounds such as copper oxides and mercury oxides,
Antifouling paints containing organic tin compounds such as tributyltin oxide, organic chlorine or organic sulfur compounds, and arsenic compounds such as phenarsazine chloride are used. Formalin and other substances were added directly to waterways. However, although these conventional aquatic organism repellents are effective, they have poor storage stability, and their effectiveness deteriorates depending on the environment in which they are used. In addition, they are selective in their effectiveness against shellfish and algae, and corrode the coating materials. Each of them has its own advantages and disadvantages, and is not necessarily satisfactory in practice. The present inventors synthesized various compounds in order to obtain a compound useful as an aquatic organism repellent, and as a result of extensive research, a novel N-substituted-4-phenylthiazolin-2-one compound, which has not yet been published in the literature, was discovered. The present invention was made based on the discovery that this is useful for repelling aquatic organisms. That is, the first invention of the present invention is based on the general formula (In the formula, R represents a hydrogen atom, an acetyl group, or a lower alkyl group, R' represents a hydrogen atom, an acetyl group, a benzoyl group, a methylbenzoyl group, or a chlorobenzoyl group, and R and R' sandwich a nitrogen atom. ) N-substituted-4-phenylthiazoline-2- can also form a phthalimide group.
The second invention is a compound with the general formula (In the formula, R represents a hydrogen atom, an acetyl group, or a lower alkyl group, R' represents a hydrogen atom, an acetyl group, a benzoyl group, a methylbenzoyl group, or a chlorobenzoyl group, and R and R' sandwich a nitrogen atom. ) N-substituted-4-phenylthiazoline-2- can also form a phthalimide group.
This is an aquatic organism repellent that contains one compound as an active ingredient. The compound of the present invention can be synthesized, for example, according to the following reaction formula. Synthesis method (1) Synthesis method (2) (In the formula, R′ has the same meaning as above, and X represents a halogen atom.) Synthesis method (3) (In the formula, R and R' have the same meanings as above,
X represents a halogen atom. ) Synthesis method (4) N-substituted-4-phenylthiazoline of the present invention
Examples of 2-one compounds are shown in Table 1.

【table】

【table】

[Seawater immersion test example]

The new compounds of the present invention [compound numbers (1) to (14)] synthesized according to the procedures of Synthesis Examples 1 to 4 were mixed in the following proportions, and thoroughly ground and mixed in a ball mill to prepare an antifouling paint. did. (% indicates weight percentage) Compound of the present invention 20.0% Petal 10.0 Talc 15.0 Barium sulfate 20.0 Vinyl resin 5.5 Rosin 5.5 Tricresyl phosphate 2.0 Methyl isobutyl ketone 11.0 Xylene 11.0 Total 100.0% This antifouling paint was used as a wash primer. once,
A test plate was prepared by brush painting twice on a steel plate (300 x 100 x 1 mm) that had been pre-treated twice with anti-rust paint (no chemicals added). This test plate was fitted into a wooden frame and suspended from an immersion raft in seawater and maintained at a depth of 1.5 m.
A test plate that had been immersed in seawater was pulled up every month, and the degree of adhesion of living organisms such as shellfish and algae on the test plate was expressed as a percentage of the total area of adhesion. The results are shown in Table 2.

【table】

Claims (1)

[Claims] 1. General formula (In the formula, R represents a hydrogen atom, an acetyl group, or a lower alkyl group, R′ represents a hydrogen atom, an acetyl group, a benzoyl group, a methylbenzoyl group, or a chlorobenzoyl group, and R and R′ sandwich a nitrogen atom. ) N-substituted-4-phenylthiazoline-2- can also form a phthalimide group.
on compound. 2 General formula (In the formula, R represents a hydrogen atom, an acetyl group, or a lower alkyl group, R′ represents a hydrogen atom, an acetyl group, a benzoyl group, a methylbenzoyl group, or a chlorobenzoyl group, and R and R′ sandwich a nitrogen atom. ) N-substituted-4-phenylthiazoline-2- can also form a phthalimide group.
1. An aquatic organism repellent characterized by containing a one-compound as an active ingredient.