JP2740823B2 - Antibacterial and antifungal agent - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a fungicide / fungicide used as an industrial bactericide or slime control agent.

[0002]

2. Description of the Related Art Conventionally, water systems in the papermaking process in the pulp and paper industry, water systems such as circulating cooling water in various industrial fields, water-based paints made using industrial water, coating solutions for paper, In latex, printing paste, leather and the like, harmful microorganisms easily propagate, and the harmful microorganisms cause various inconveniences. Particularly, in the papermaking process of the paper pulp industry, wall chests where pulp slurry flows,
Slime adheres to flow boxes, transport pipes, etc.
This desorbs and mixes into the paper pulp product, causing various colored spots and stains, causing problems such as contamination of the paper pulp product, paper breakage, and reduced production efficiency, and is a major obstacle to paper pulp production. ing. Since various kinds of microorganisms such as bacteria, actinomycetes, filamentous fungi, and yeasts are involved in the production of such slime, in order to sterilize or suppress these microorganisms, antibacterial and antifungal treatment is performed during the papermaking process. It has been practiced to add an agent as a slime control agent. The cause of slime generation has been bacteria in many cases, but filamentous fungi are the main cause due to the progress of closed industrial water, neutralization of papermaking, or the increase in the percentage of waste paper. The occurrence of possible slime troubles has increased. However, few of the conventional drugs have a sufficient antifungal effect and act mainly on bacteria, and thus cannot completely prevent slime trouble.

[0003]

SUMMARY OF THE INVENTION An object of the present invention is to provide a fungicidal / fungicidal agent which can effectively suppress the growth of bacteria and fungi.

[0004]

Means for Solving the Problems The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have completed the present invention. That is, according to the present invention, an α-chlorobenzaldoxime acetate compound represented by the following general formula (I) and / or a chloroisothiazoline compound represented by the following general formula (III) are combined with the following general formula (II) An antiseptic / fungicide characterized by containing an isophthalonitrile compound represented by the formula (1) as an active ingredient.

Embedded image (Where n represents an integer of 0 to 2)

Embedded image

Embedded image (Wherein, R represents an alkyl group or alkenyl group having 1 to 18 carbon atoms)

The α-chlorobenzaldoxime acetate compound represented by the general formula (I), which is one component of the fungicide / fungicide of the present invention, is a known compound (JP-B-51-331).
71), and isophthalonitrile-based compounds represented by the general formula (II) and chloroisothiazoline-based compounds represented by the general formula (III) are also known compounds. However, the antibacterial effect can be expected only for certain types of microorganisms. The fungicidal / fungicidal agent of the present invention contains the compounds of the above-mentioned general formulas (I) and / or (III) and the general formula (II). That is, the fungicidal and fungicide of the present invention comprises a compound of the general formula (I), a compound of the general formula (II) and a compound of the general formula (I)
The compound of the general formula (I), the compound of the general formula (II) and the compound of the general formula (I)
The compound of the formula (II) and the compound of the formula (II) can be contained.

When the compounds of the general formulas (I), (II) and (III) are used in combination, the weight ratio thereof is
Compound of general formula (I): 10-90 wt%, preferably 30-70 wt%, compound of general formula (II): 10-9
0 wt%, preferably 30 to 70 wt%, of the general formula (II)
Compound of I): 10 to 90% by weight, preferably 30 to 7%
0 wt%. When the compound of the general formula (I) and the compound of the general formula (II) are used in combination, the weight ratio of the compound of the general formula (I): 10
-90 wt%, preferably 30-70 wt%, compound of the general formula (II): 10-90 wt%, preferably 30
７０70 wt%. When the compound of the general formula (II) and the compound of the general formula (III) are used in combination, the compound of the general formula (II): 10 to 90 w
t%, preferably 30 to 70 wt%, of the general formula (III)
Compound: 10 to 90 wt%, preferably 30 to 70 w
t%.

By combining the compounds of the general formulas (I) to (III) as described above, it is possible to obtain an excellent fungicidal and fungicidal effect which cannot be achieved by each compound alone. The fungicidal / fungicidal agent of the present invention exhibits an excellent fungicidal effect, especially against a wide variety of fungi.

The germicidal and fungicide of the present invention is generally used as a solvent solution or an emulsified dispersion. Examples of the solvent that can be used include alcohol solvents, ketone solvents, ether solvents, and hydrocarbon solvents.
In addition, any of the compound components may be supported on a carrier for use. The fungicidal / fungicidal agent of the present invention may contain other fungicidal / fungicidal active ingredients, stabilizers, surfactants and the like as long as the object of the present invention is not impaired. The amount of the fungicidal and fungicide of the present invention to be used is generally 0.0% in the case of an aqueous system in the field of the pulp and paper industry.
It is 1 to 100 ppm, and 1 to 500 ppm in the field of water-based paint, glue, leather and the like, and a good antibacterial and antifungal effect can be obtained with this amount of addition.

[0009]

Next, the present invention will be described in more detail with reference to examples. In addition, the part shown below means a weight part.

Example 1 α-chlorobenzaldoxime acetate 10 parts 5-chloro-2,4,6-trifluoroisophthalonitrile 5 parts Propylene carbonate 85 parts Example 2 5-chloro-2,4,6-trifluoro Loisophthalonitrile 5 parts 4,5-Dichloro-N (n-octyl) -isothiazolin-3-one 25% phenylxylylethane solution 10 parts Propylene carbonate 85 parts Example 3 α-chlorobenzaldoxime acetate 5 parts 5 -Chloro-2,4,6-trifluoroisophthalonitrile 2.5 parts 4,5-dichloro-N (n-octyl) -isothiazolin-3-one 25% phenylxylylethane solution 5 parts propylene carbonate 87.5 Department

Comparative Example 1 a-chlorobenzaldoxime acetate 10 parts Propylene carbonate 90 parts Comparative example 2 5-chloro-2,4,6-trifluoroisophthalonitrile 5 parts Propylene carbonate 95 parts Comparative example 3 4,5- Dichloro-N (n-octyl) -isothiazolin-3-one 25% phenylxylylethane solution 10 parts Propylene carbonate 90 parts

The antibacterial and antifungal agents prepared in the above Examples 1 to 3 and Comparative Examples 1 to 3 were examined for the effect of preventing the growth of bacteria and the effect of preventing the generation of slime by the following test methods.

Test Example 1 [Inhibitory Effect] A part of an Aspergillus niger colony was taken, suspended in a physiological saline solution, divided into test tubes in equal volumes, and added with a waxman's medium. A predetermined amount of each drug was added, and shaking culture was performed at 32 ° C. Twenty-four hours later, the degree of propagation of the microorganism was examined, and the growth inhibitory concentration (ppm) of the microorganism was determined based on the result. Table 1 shows the results of the culture.

[Table 1]

[0015] In Table 1, ++ indicates that the microorganism clearly proliferated, ± indicates that the growth of the microorganism was slightly observed, and-indicates that the growth of the microorganism was not observed. These symbols have the same meaning in Table 2 below.

Test Example 2 [Inhibition Test] A part of a colony of Geotricum spp.
The test was performed in the same manner as in Test Example 1. Table 2 shows the results of the culture.

[0017]

[Table 2]

Test Example 3 [Bactericidal test] A part of a colony of Aspergillus niger was taken, suspended in physiological saline, divided into test tubes in equal amounts, and a predetermined amount of each of the above-mentioned drugs was added thereto. After standing for 15 minutes, the mixture was diluted with a large volume of physiological saline, and 1 ml of this solution was mixed with a heated and dissolved waxman agar medium, and solidified.
Culture was performed at 2 ° C. After 48 hours, the degree of propagation of the microorganisms is checked, and the results show the bactericidal concentration (ppm) of the microorganisms.
Was determined. Table 3 shows the results of the culture.

[0019]

[Table 3]

In Table 3, ++ means that 100 or more colonies were found, + means 10 or more but less than 100 colonies, and ± means 1 to less than 10 colonies. The symbol-indicates that no growth of microorganisms was observed. These symbols have the same meaning in Tables 4 and 5 described later.

Test Example 4 [Inhibition Test] A part of a colony of Geotrichum spp.
The test was performed in the same manner as in Test Example 3. Table 4 shows the results of the culture.

[0022]

[Table 4]

From the above Test Examples 1-4, it can be seen that the agent of the present invention has a synergistic effect on the growth inhibiting effect and the bactericidal effect of the microorganism.

Test Example 5 A sterilization test using chemicals was performed using white water from a papermaking company. Tables 5 to 7 show the results of the culture. The filamentous fungi isolated from the white water were those belonging to the genera Pissilomyces, Acremonium and Geotricum. Table 5 shows the results of cultivation of Psiromyces sp., Table 6 shows the results of cultivation of Acremonium sp., And Table 7 shows the results of cultivation of Geotricum sp.

[0025]

[Table 5]

[0026]

[Table 6]

[0027]

[Table 7]

From the results of Test Example 5, it is clear that the agent of the present invention has an excellent bactericidal effect against filamentous fungi in white water of a paper company.

[0029]

Industrial Applicability The fungicidal / fungicidal agent of the present invention exhibits excellent growth inhibitory and bactericidal effects against various microorganisms, especially a wide range of filamentous fungi, due to the synergistic effect of each component contained therein. It is advantageously used as a bactericide, a slime control agent and the like.

 ──────────────────────────────────────────────────続 き Continuation of the front page (72) Inventor Susumu Mitsui 4-11-2 Ginza, Chuo-ku, Tokyo Inside Sommar Corporation (56) References JP-A-3-184904 (JP, A) JP-A Heisei 5-70306 (JP, A) JP-A-6-40811 (JP, A) JP-B-41-11358 (JP, B1)

Claims (1)

(57) [Claims] 1. An α-chlorobenzaldoxime acetate compound represented by the following general formula (I) and / or a chloroisothiazoline compound represented by the following general formula (III), and a compound represented by the following general formula (II) An antiseptic / antifungal agent comprising an isophthalonitrile compound as an active ingredient. Embedded image (Wherein, n represents an integer of 0 to 2) Embedded image (Wherein, R represents an alkyl group or alkenyl group having 1 to 18 carbon atoms)