JPS5929161B2 - Volatile antibacterial and antifungal preparation - Google Patents

Description

[Detailed description of the invention] The present invention relates to a volatile antibacterial and antifungal preparation.

Conventionally, antibacterial and antifungal agents have been widely used in the fields of packaging materials, metals, fibers, plastic materials, rubber, agricultural chemicals, and the like. The types of antibacterial and fungicidal agents include copper-based agents, mercury-based agents, organotin-based agents, chlorinated phenol-based agents, quaternary ammonium-based agents, organic nitrogen-based agents, organic nitrogen-sulfur-based agents, A large number of compounds are known, including organic bromine drugs. Generally, these chemical treatment methods include surface treatments such as spraying, coating, injection, and mixing, or internal treatments.
However, when applying antibacterial and fungicidal agents, there are many cases where it is difficult or disliked to directly treat the target object or place. Examples include antibacterial and antifungal treatments for food packaging materials, pharmaceutical packaging materials, clothing, textiles, leather raw materials and their products, agricultural products, and the like. Therefore, the present inventor has investigated various effective antibacterial and mildew prevention methods that are sustainable for a certain space and object without directly applying surface treatment to the object or place.
Most of the conventionally used antibacterial and fungicidal agents have poor volatility and are ineffective without direct surface treatment, and those that are volatile have weak practical effects and cannot be expected to last. However, by using a sublimating compound together with an antibacterial and fungicidal agent with a specific chemical structure, the synergistic action of the latter allows direct surface treatment of a certain space or object. The present inventors have discovered that a long-lasting and highly effective antibacterial and antifungal effect can be achieved without the use of antifungal agents, and have completed the present invention. That is, the present invention is based on the general formula (I
) (where R represents a methyl group or a chlorine atom) as an active ingredient, and naphthalene, dichlorobenzene, di-butylphenol as a synergist.
- A volatile antibacterial and antifungal agent containing one or more sublimable compounds selected from the group consisting of butylbenzene, acetaldehyde trimer, propylaldehyde trimer, and isobutyraldehyde trimer. .

The general formula (
1) Representative examples of the indicated t-butylphenol compounds are listed below.

6-t-butyl-meta-cresol, 5-t-butyl-meta-cresol, 4-t-butyl-meta-cresol,
6-t-butyl-ortho-cresol, 5-t-butyl-ortho-cresol 4-t-butyl-ortho-cresol, 3-t-butyl-ortho-cresol, 2-t-butylpara-cresol, 3-t-butyl-ortho-cresol Butyl-para-cresol, 4-t-butyl-2-chlorophenol, 4-t
-butyl-3-chlorophenol, 3-t-butyl-6-
Examples include chlorphenol, 3-t-butyl-4-chlorophenol, and the like.

Further, the sublimable compound in the present invention is preferably an aromatic sublimable compound having a structure similar to the active ingredient t-butylphenol compound and a lower alkyl aldehyde trimer, which have an excellent effect as a synergist. There is. Specifically, naphthalene, p-dichlorobenzene, m-dichlorobenzene, 0-dichlorobenzene, di-t-butylbenzene,
Examples include acetaldehyde trimer, propylaldehyde trimer and isobutyraldehyde trimer. The volatile antibacterial and antifungal preparation of the present invention has strong growth inhibiting activity against a wide range of bacteria, yeast, and mold. The method for producing the Q-dryogenic antibacterial and antifungal preparation of the present invention is directed to the t-
There is a method in which a butylphenol compound and a sublimable compound are simply mixed and compressed into a tablet, or a method in which the mixture is heated, melted, mixed, and then cooled and molded. Furthermore, binders, colorants, flavoring agents, other antibacterial and antifungal agents, insecticides, and the like may be added to the antibacterial and antifungal formulation of the present invention, if necessary.

When the antibacterial and antifungal agent of the present invention is placed in a space of a certain size at a certain interval, it exhibits an antibacterial and antifungal effect on places and objects contained in that space. Specifically, the places where it is used are indoors in cupboards, drawers, closets, geta boxes, floors, storage sheds, trash cans, furniture, clothing cases, boxes, etc., and outdoors in warehouses, vinyl houses, etc. Examples include inside a greenhouse.

Regarding the composition ratio of the volatile antibacterial and antifungal preparation of the present invention, the t-butylphenol compound represented by general formula (1) is added as an active ingredient in the range of 0.01 to 10.0% by weight. It is desirable that the amount of the sublimable compound is 70 to 95% by weight.

Hereinafter, the present invention will be specifically explained with reference to Examples. Example 1 Plastic container at room temperature 25°C (vertical 50C7711 horizontal 5
Tablets (diameter 10crrL) obtained by dissolving, cooling and molding the antibacterial and antifungal agent 1.07 and the sublimation compound 1007 in a tablet (diameter 10crrL), antibacterial and antifungal agent 1.07 Chisels in a petri dish with a diameter of 4 (1) and 10
Place each test sample of a tablet (diameter 4?) obtained by heating, dissolving, cooling, and molding only the sublimable compound of No. In the case of mold, the fungus was inoculated at one point and the growth status was observed.

Those with growth inhibiting activity have poor growth conditions compared to untreated plots.

In the case of bacteria, the number of colonies in the first week was determined, and in the case of mold, the diameter of the colonies in the first week was determined, and the results are shown in Table 1.
It is shown in Table 2. In either case, the smaller the value, the stronger the activity. As is clear from Tables 1 and 2, the products of the present invention exhibited a superior inhibitory effect than any of the control products. This indicates that the product of the present invention containing a specific t-butylphenol compound and a sublimable compound is an excellent volatile antibacterial and fungicidal agent. It has been shown that the combination of a drug and a sublimable compound does not have an excellent volatile antibacterial and antifungal effect. Example 2 A 0.17 antibacterial and antifungal agent and 1
A tablet (diameter 3?) obtained by heating, melting, cooling, and molding the sublimable compound of No. The growth status was observed.

Those with growth inhibiting activity have poor growth conditions compared to untreated plots. The results are shown in Table 3.

In the case of bacteria, the number of colonies after the first week was examined, and in the case of mold, the diameter and length of the colonies after the first week were examined, and efficacy was determined by comparing with the untreated plot. In Table 3 VC, those with a significant growth inhibition effect compared to the untreated area are indicated as having antibacterial and antifungal effects (A), and those with a slight superiority difference are indicated as antibacterial and antifungal. Those with anti-fungal effect are indicated as (e), and those for which no superiority difference was observed are indicated as having no anti-bacterial and anti-mildew effect.
(c) is displayed. As is clear from the results in Table 3, excellent antibacterial and antifungal effects were observed in all of the formulations of the present invention. The drugs of the present invention and control drugs tested are shown below.

Da*This invention (
1): 6-t-butyl-meta-cresol 0.1f + isobutyraldehyde trimer 107 (3): 4-t-butyl-3-chlorophenol 0.17 + P-dichlorobenzene 107 Control (Il): 4-chloro- Meta-cresol-0,1y+
Nanaphthalene 107 IV): 4-Chlor-Sym-metaxylenol 0.17 + isobutyraldehyde trimer 107 Example 3 Penicillium luteum in the wardrobe (5001),
An aqueous solution containing a strain of Alpergillus niger was sprayed onto pure wool fabric, kept in a wardrobe at 25°C, and a test sample of 1017, which had been compressed into tablets, was hung. Table 4 shows the results of observing the growth status of.

Those with a clear growth inhibition effect compared to the untreated product are indicated as having an antibacterial and antifungal effect (A), and those that are slightly superior are indicated as having a slight antibacterial and antifungal effect (T). )
When compared with untreated products, those with the same level of antibacterial and antifungal effect were indicated as (g). As shown in Table 4, all the formulations of the present invention exhibited excellent antibacterial and antifungal effects. Example 4 A black men's cow shoe with a moistened surface was placed in a heated box (3001), the inside of the heated box was kept at 25°C, and the tablets were compressed into 5.0
Four of the 57 test samples were placed in each corner, and the growth status of mold on the surface of the cow shoes was observed after one week.Table 5 shows the results.
It was shown to.

Those with a clear growth inhibiting effect compared to the untreated product are labeled as having an antibacterial and antifungal effect (4), and those that are slightly superior are labeled as having an antibacterial and antifungal effect (I). ), and those for which no superiority difference was observed compared to untreated were indicated as (c) as antibacterial and antifungal effects. As shown in the results in Table 5, all of the formulations of the present invention exhibited excellent antibacterial and antifungal effects. Example 5 Strawberries were grown in an outdoor greenhouse (5 m long, 10 m wide, 4 m high).
One test sample of 10.1y each was placed in the nursery of a plastic container (50CTn vertically, 100CTIL horizontally, 50cm high) in which cucumbers and tomatoes are grown.
Table 6 shows the results of observing the rates of strawberry gray mold, cucumber powdery mildew, cucumber mildew, and tomato canker after a week.
It was shown to.

The lower the disease rate, the stronger the antibacterial effect. As is clear from Table 6, all the formulations of the present invention exhibited excellent antibacterial and antifungal effects. Example 6 One test sample of 3.037 was placed in a plastic container (vertical 20? x width 20 (1, height 20?) containing 50 Satsuma mandarin fruits, and left in a room at 20°C. Observe the disease state after 2 weeks.

Claims (1)

[Claims] 1 General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (However, R
The active ingredient is a t-butylphenol compound represented by methyl group or chlorine atom, and the synergist is naphthalene, dichlorobenzene, di-t-butylbenzene, acetaldehyde trimer, propylaldehyde trimer. A volatile antibacterial and antifungal preparation containing one or more sublimable compounds selected from the group consisting of isobutyraldehyde trimer and isobutyraldehyde trimer.