JP2722503B2 - Industrial fungicide - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to industrial fungicides such as water-based and oil-based paints, emulsion resins, adhesives, plastics, leather, wood, silicone caulks, fibers and the like.

<Conventional Technology> Conventionally, 2-methoxycarbonylaminobenzimidazole has been widely used as an industrial fungicide.

The present compound has an antifungal effect at a low concentration and is an antifungal agent excellent in stability against heat, ultraviolet rays, pH, etc., toxicity, and skin irritation.

However, this compound is not useful for some bacteria, especially Rhizopus Stoloni.
The antifungal effect was weak against fer and Chaetomium Globosum, and sometimes the industrial products containing this compound were contaminated with microorganisms.

<Problems to be Solved by the Invention> In order to solve the problems of industrial products containing 2-methoxycarbonylaminobenzimidazole, isolation and identification of bacteria from industrial products that have been contaminated with microorganisms for the purpose of investigating the cause. Was carried out.

<Means for Solving the Problems> The present inventors have conducted intensive studies on a fungicide having an antifungal effect against this isolated bacterium, and as a result, tetrachloromethylsulfonylpyridine is very useful. When they were used in combination with 2-methoxycarbonylaminobenzimidazole, they found that the antibacterial spectrum was broadened and that they had an excellent synergistic effect, thereby completing the present invention.

That is, the present invention provides an industrial fungicide containing 2-methoxycarbonylaminobenzimidazole (A) and tetrachloromethylsulfonylpyridine (B).

Since 2-methoxycarbonylaminobenzimidazole (A) has low solubility in general organic solvents, it is used in the form of aqueous hydrochloric acid salts, disperses, powders, and wettable powders. Tetrachloromethylsulfonylpyridine (B) is soluble in organic solvents such as N, N-dimethylformamide and cyclohexanone, but these solvents cannot be used in the (A) / (B) mixture. Preferably, the compound (A) / (B) mixture is a disperse type preparation, a preparation dispersed in an emulsion resin, a powder, or a wettable powder. Compounds (A) / (B) are compounds having excellent stability, and almost no decomposition is observed in the above mixed preparation.

Since compound (A) is insoluble in water and hardly soluble in organic solvents, powders, aqueous solutions of mineral salts, emulsions, etc., depending on the purpose, solvents or surfactants for improving the stability of the preparation at low temperatures can be used. Used in addition.

As the solvent, glycol solvents such as ethylene glycol, diethylene glycol, dipropylene glycol, and alcohol solvents such as methanol and ethanol are used. As the surfactant, a nonionic or anionic surfactant is preferably used. As the nonionic surfactant, a polyoxyethylene type such as polyoxyethylene styrenated phenol, polyoxyethylene phenyl ether, polyoxyethylene alkyl ether is used. And polyhydric alcohol esters such as sorbitan fatty acid esters. As the anionic surfactant, an alkali aryl sulfonate is preferable, and examples thereof include sodium alcarbbenzene sulfonate.

The mixing ratio of the compound (A) and the compound (B) is slightly different depending on the purpose, but usually 0.1 to 1 part, preferably 0.2 part, of the compound (B) per 1 part (the same or less by weight) of the compound (A).
0.6 parts, more preferably (A) :( B) = 4: 1.

The content of the active ingredient in the fungicide of the present invention varies depending on the dosage form and the purpose of use, but is generally about 1 to 30% by weight, preferably 10 to 30% by weight. Depending on the purpose of use, the solvent and surfactant are preferably used in an amount of 1 to 30% by weight based on water.

The antifungal agent of the present invention can be used by adding a pH adjusting buffer, an antifreezing agent, a fragrance, an antifoaming agent, another antifungal agent and the like. Other fungicides include halogenated phenols,
Tetrachloroisophthalonitrile, diiodomethyl-p
-Tolylsulfone, 4-chlorophenyl-3-iodopropargyl formal, and the like, but are not limited to these examples.

<Effect of the Invention> By mixing 2-methoxycarbonylaminobenzimidazole and tetrachloromethylsulfonylpyridine, the antibacterial spectrum is broader than when each is used alone,
An excellent synergistic effect, which was not known before, can be obtained. It should be noted that mixing of both compounds does not cause a problem in stability and toxicity.

<Examples> Examples are given below to specifically describe the antibacterial activity and practical effects of the present invention.

<Example 1> The mixture obtained by the present invention and its two compounds were each tested for antibacterial activity against mold by using a PSA medium at 28 ± 2 ° C for 7 days. I asked. The mixture used here was 2-
Methoxycarbonylaminobenzimidazole (A):
Tetrachloromethylsulfonylpyridine (B) = 4: 1. The results are shown in Table 1. From the results shown in Table 1, the mixture of the present invention is effective for all test bacteria at a low concentration,
The antimicrobial spectrum was broadened, and a synergistic effect due to the combined use of the two drugs was observed. Especially Rhizopus stolonifer, C
A synergistic effect was clearly observed for haetomium globosum by using the compounds (A) and (B) together.

General organic drugs are often less effective against Rhizopus stolonifer and Chaetomium globosum (A),
By using (B) in combination, it was found that the width of the antibacterial spectrum was widened, and that the overall effect in terms of effect and cost was extremely large as compared with the use of a single agent.

<Example 2> Antifungal test of acrylic emulsion paint film (A) and (B) were mixed at a ratio of 4: 1 and dispersed in an acrylic emulsion resin. A mold-proof comparative test was performed on the type preparations (A) and (B) alone. As the test method, the items of JIS-Z-2911 mold resistance test method paint were used. The test bacteria were tested in two ways, one for testing general industrial products and one for testing paints. The results are shown in Tables 2 and 3. As a result, (A) alone has a weak effect on bacteria for testing general industrial products,
(B) It turns out that it is slightly weak to the bacteria for a paint test by itself.
On the other hand, it can be seen that the mixture of the present invention is effective in any of the two tests.

Test bacteria: Aspergillus niger Penicillium citrinum Rhizopus stolonifer Cladosporium cladosporioides Chaetomium globosum for testing general industrial products Test bacteria: Aspergillus niger Penicillium funiculosum Cladosporium cladosporioides Aureobasidium Pullulans Gliocladium rirens for paint test <Example 3> Mold control test of European red pine Using the same preparation as in Example 2, a mold control test was carried out on wood pieces. The test method uses European red pine as a test material and JIS
-Z-2911 Mold resistance test, wood and bamboo products were used.
The test bacteria are a total of 6 bacteria, 5 bacteria specified in the item of wood and bamboo products and 1 bacteria isolated from the European red pine by the present inventors.
Table 4 shows the results.

Thus, (A) alone has a weak effect on Rhizopus and Ketomium, and (B) alone has a weak effect on European red pine isolates. The mixture of (A) and (B) of the present invention suppressed the generation of bacteria, and a synergistic effect was confirmed from the results.

Test bacteria: Aspergillus niger Penicillium citrinum Rhizopus stolonifer Cladosporium cladosporioides Chaetomium globosum European red pine isolate for testing general industrial products and wood and bamboo products

Claims (1)

(57) [Claims] 1. An industrial fungicide containing 2-methoxycarbonylaminobenzimidazole (A) and tetrachloromethylsulfonylpyridine (B).