JPS6056135B2 - N-propioloylindoline compound - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel and useful N-propioloylindoline compounds.

At present, algae such as blue laver, sea lettuce, seaweed, miru, and arame are attached to and propagate on equipment and equipment that are submerged in water for long periods of time, such as fishing nets, ship bottoms, underwater structures, and cooling channels, causing many problems. is causing.

For example, in fixed fishing nets used for fish and shellfish farming to artificially secure marine resources, the above-mentioned algae can grow attached to the nets, impairing their durability or blocking the nets. Insufficient movement of seawater within the net causes fish to die due to lack of oxygen, and also promotes the proliferation of bacteria, causing damage to fish due to Nocardia disease, Benetenia disease, etc.

Furthermore, when the above-mentioned algae grow in cooling waterways, etc., not only does the amount of water intake decrease and cooling efficiency decreases, but it also causes corrosion of equipment, causing economic damage. Conventionally, organometallic compounds and organochlorine compounds have been used to control these harmful algae, but these are undesirable from the standpoint of environmental pollution, and the development of new agents has been desired.

In order to solve these problems, the present inventors synthesized various compounds, investigated their algal adhesion control effects, and as a result of intensive research, a novel N-propioloylindoline compound represented by the following formula was developed. The present invention was completed based on the discovery that this is useful for preventing the adhesion of harmful algae.

The novel N-propioloylindoline compound of the present invention is represented by the following formula.

The novel N-propioloyl indoline compound of the present invention is
For example, it can be synthesized by reacting propiolic acid chloride and indoline in the presence of a dehydrochlorination agent such as N,N-diethylaniline, as shown in the reaction formula below.

The novel N-propioloylindoline compound of the present invention has an effect of preventing the adhesion of harmful algae and can be used as an algae preventive agent.

Next, the synthesis and usefulness of the novel N-propioloylindoline compound of the present invention will be specifically explained using Examples.

[Example 1] 25 equipped with a stirrer, cooling tube, dripping load and thermometer
Propiolic acid chloride 8 in a 0ml four-necked reaction flask
．． Add 8f (0.1 mol) and 40 ml of chloroform and cool to -50°C with dry ice-acetone from the outside.
A mixed solution of 11.9y (0.1 mol) of indoline, 14.9f (0.1 mol) of N,N-diethylaniline, and 60 ml of chloroform was added dropwise thereto over a period of 1 hour while maintaining the temperature.

After the dropwise addition was completed, cooling was stopped, and the mixture was stirred for about 1 hour until the temperature of the reaction solution returned to room temperature, and further stirred at room temperature for 1 hour to allow reaction. After the reaction was completed, the resulting reaction mixture was washed with water and treated with N,
After separating and removing N-diethylaniline hydrochloride and drying, chloroform was distilled off to obtain a solid product, which was recrystallized from carbon tetrachloride to obtain N-propioloylindoline having the following structural formula. I got 120y. Yield 70.2%
. In addition, compounds can be analyzed by gas chromatography, infrared spectroscopy,
It was identified by nuclear magnetic resonance spectroscopy.

Structural formula: 1"1"~"\-" Molecular formula: CllH,NO Molecular weight: 171.2 Appearance: Yellow powder crystal Melting point: 111-113 C [Example 2] Enteromorpha compressor [EnterOmOrphaCOmpressa (Hiraao Nori)] 78 ml of seawater containing 500 to 100 spores per ml is dispensed into 100 ml flat culture flasks.

To this, the novel N-propioloylindoline 2f1 cyclohexanone 90fI1 emulsifier Tw of the present invention is added in advance.
2 ml of each of emulsions with active ingredient concentrations of 1%, 0.2%, and 0.08% prepared by blending een-80 (component: polyoxyethylene sorbitan monooleate) 8y and diluting with distilled water. In addition, the drug concentrations in the culture flasks were adjusted to 5 ppm, 1 ppm, and 0.2 ppm, respectively. The culture flask thus treated was placed in a place kept at a room temperature of 20 C and illuminated with 300 lux of light using a white fluorescent lamp, and was exposed to 200 lux per minute in the culture medium.
Proceed with the culture while supplying air at a rate of ~300ml,
Enteromorpha that adhere to the culture flask wall over time
The state of attachment and extension of the compressor was observed.

The results are shown in Table 1. The state of adhesion and extension was determined according to the following criteria. (Judgment Criteria) In addition, we conducted the same test using tributyltin oxide, which is used as an algaecide for fishing nets, in place of the control and N-propioloyl indoline, and the results were similar to those obtained without adding any chemicals. Also listed in Table 1.

Claims (1)

[Claims] 1 N-propioloylindoline compound.