JPS6253904A - Fungicidal composition - Google Patents

Abstract

PURPOSE:To provide a fungicidal composition effective to inhibit the deterioration of industrial material with fungus, by combining one or more 4-alkoxy-2,5,6- trifluoroisophthalonitrile compound with a certain kind of benzimidazole compound. CONSTITUTION:The objective fungicidal composition contains, as active components, (A) 1pt.wt. of one or more 4-alkoxy-2,5,6-trifluoroisophthalonitrile compounds (e.g. 4-methoxy-2,5,6-trifluoroisophthalonitrile) and (B) 0.02-1.0pt.wt. of one or more compounds selected from methyl 2-benzimidazolecarbamate, 2-(4-thiazolyl)benzimidazole and methyl 1-butylcarbamoyl-2-benzimidazole carbamate. EFFECT:The composition can be applied without causing environmental pollution and has high economic advantage.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to antibacterial compositions, and more particularly, to antibacterial compositions for preventing the quality of general industrial materials such as paints, wood and bamboo products, leather, fibers, wall materials, ceiling materials, etc. The present invention relates to an antibacterial composition that can effectively prevent deterioration and also prevent the adverse effects of microorganisms on parts of production plants in connection with industrial materials, such as cooling water circulation systems and cooling lubricant oil circulation systems.

Conventional Technology Conventionally, various industrial materials and products such as wood, pulp, paper, fibers, paints, adhesives, and synthetic resins often have mold, rotting fungi, bacteria, etc., which not only contaminate the appearance but also damage the substrate. The quality of the materials and products was often compromised, such as deterioration of the materials.

For this reason, organic tin compounds and chlorinated phenol compounds such as pentachlorophenol trichlorophenol have been used as effective control means, and these compounds are widely used because they are relatively inexpensive.

However, these compounds do not have antibacterial activity against a wide range of types of bacteria, and are highly toxic to humans and animals. There are problems in that there is a risk of secondary damage or environmental pollution caused by incineration of the product.

In order to meet these demands, much effort has been made to develop safer antibacterial agents, but many are only effective against relatively prevalent bacteria or require use in large amounts. However, many of them are ineffective or difficult to put into practical use due to economical reasons, and the above requirements have not been met. Recently, the antibacterial properties of aromatic fluorinated dinitrile compounds have been reported. This compound is 4-alkoxy-2,5,6-drifluoroisophthalonitrile, and it is known that the lower the molecular weight of the alkoxy group at the 4-position, the higher the antibacterial activity. In actual use, it has disadvantages in terms of cost performance compared to conventional drugs, and has not yet been put into practical use.

On the other hand, some benzimidazole compounds have already been used as bactericidal agents and have been evaluated as fairly safe drugs, but on the other hand, they do not have a sufficient antibacterial spectrum and are expensive, so they cannot be used alone. There were various obstacles to doing so.

Problems to be Solved by the Invention The present inventors have solved the problems of the conventional antibacterial compounds described above, which have antibacterial activity against a wide range of types of bacteria, are free from environmental pollution, and are economical. In view of the fact that there was no superior product, we conducted intensive research to solve this problem and found that at least one 4-alkoxy-2,5,6-trifluoroisophthalonitrile compound and a benzimidazole compound It was discovered that the above object could be achieved by using certain materials in combination, and this led to the present invention.

Means for solving the problems and their effects, that is, according to the present invention, (A) at least one 4-alkoxy-2,5,6-trifluoroisophthalonitrile compound and (B) 2-benz methyl imidazole carbamate, 2-(4-thiazolyl)benzimidazole and 1
An antibacterial composition containing as an active ingredient at least one compound selected from methyl -butylcarbamoyl-2-benzimidazolecarbamate is provided.

By using the antibacterial composition according to the present invention, it is possible to reduce the amount of drugs used as a whole, lower processing costs, improve safety for humans and livestock, and furthermore, by using large amounts of drugs, it is possible to reduce the amount of drugs used. An excellent effect can be obtained in that environmental destruction caused by this method can be prevented.

In the present invention, the 4-alkoxy-2,5,6-drifluoroisophthalonitrile compound used as component A is a compound represented by the following formula (1).

(In the formula, R is CH3, C2H5, n C3H7, i
C3H7, n-C4Hg, t-C4)is. ) On the other hand, the compound used as component B in the present invention is a benzimidazole compound such as methyl 2-benzimidazolecarbamate (formula ■), 2-(4-thiazolyl)benzimidazole (formula ■), or 1-butylcarbamoyl. -2-benzimidazole methylcarbamate (■
formula).

CON HC4Ha There is no particular change in the blending ratio of the A component and the B component in the antibacterial composition of the present invention, and it can be changed arbitrarily. .0
When 2 to 1.0 parts by weight is blended, the synergistic effect is particularly significant, which is preferable.

There are no particular restrictions on the method of using the antibacterial composition of the present invention, and it may be added to the target material or product as it is, but depending on the method of use, it may be mixed with an appropriate liquid or solid carrier, or it may be further mixed with a dispersant, By adding suspending agents, penetrants, wetting agents, stabilizers, etc., the composition can be used in dosage forms such as wettable powders, emulsions, solubilizers, powders, granules, pastes, and sprays. Furthermore, the antibacterial composition of the present invention can be blended with other bactericidal agents, insecticides, deterioration inhibitors, etc., and used in the same manner as known antibacterial agents. The antibacterial composition according to the present invention can contain the above-mentioned components by any conventionally known method.

The antibacterial composition of the present invention is effective against a wide range of bacteria that grow in various places where the A and B components are combined at low concentrations that would be impractical if used alone. It exhibits an excellent antibacterial effect, and its practical value is extremely high.

EXAMPLES AND TEST EXAMPLES The present invention will be explained in more detail below according to Examples and Test Examples, but it goes without saying that the scope of the present invention is not limited to these Examples.

In addition, the abbreviations of compound names in the table below are as follows.

Component A Me-TFPN4-methoxy-2,5,6-1-lifluoro-isophthalonitrile Et-TFPN4-ethoxy-2,5,6-)lifluoro-isophthalonitrile Pr-TFPN4-propoxy-2,5,6 -) Refluoro-isophthalonitrile i -Pr-TFPN 4-isopropoxy-2,5
, 6-dolifluoroisophthalonitrile Bu-TFPN 4-butoxy-2,5,6-dolifluoroisophthalonitrile 1-Bu-TF PN 4-isobutoxy-2,5,
6-Dorifluoroisophthalonitrile B component BCM 2-benzimidazole methylcarbamate TBZ 2-(4-thiazolyl)benzimidazole BEN 1-7'Tylcarbamoyl-2-benzimidazole methylcarbamate Example 1 In Table 1 An oil agent was obtained by mixing and dissolving each component having the composition shown (wt%).

Example 2 An emulsion was obtained by mixing and dissolving each component having the composition (% by weight) shown in Table 2.

Example 3 Each component having the composition (% by weight) shown in Table 3 was mixed and ground to obtain a wettable powder.

[Explanation of test example]

In order to specifically explain the effects of the composition of the present invention, typical test examples are shown below.

However, this is just an example, and it goes without saying that the examples of application of the present invention are not limited to these.

Test Example 1 is a test using mold. Components A and B alone are effective against mold at a level of 100 OP, but when combined, they have the same efficacy at 1/3 to 115 of that concentration. The synergistic effect is remarkable.

Test Example 2 uses wood and wood materials such as jelutong and verdicle board, but jelutong is a South Sea wood and is a material that is extremely susceptible to mold growth. When actually treating wood, we use both oil and emulsion, so we treated it with both forms. The same effect will be shown at a concentration of about 1/3 of that when each of component A and component B is used alone.

In Test Example 3, the A component and the B component do not have much of an effect when used alone, but when mixed together, the effect becomes clear at the same concentration, and a synergistic effect is exhibited.

Test Example 4 is an efficacy test against wood-decaying fungi that decompose wood components and cause a decrease in the strength of wood.

As a standard, a potency value of 80 or higher is determined to be effective. Component A alone requires a concentration of 2.0% or more, but a mixture of component A and component B is effective against these bacteria at even lower concentrations.

Test Example 1 Efficacy comparative test of antibacterial composition by 3 paper disk method Three paper disks (φ8 m) for antibiotic assay were immersed for 5 seconds in a solution prepared by diluting the composition shown in Example 2 to a predetermined concentration. do. 12
After air drying for a while, it was used in experiments. PDA medium 20-
Place one sheet of treated 3 paper on one Petri dish into which Aspergillus niger was dispensed.
The spore suspension 2- of r) was sprayed uniformly. 28℃
It was stored in a thermostatic chamber adjusted to ±2°C, and the growth state of the mycelium was observed after 48 hours. Similar tests were performed on Rhizopus nigricans and Trichoderma viridani.
viridae).

The test results were evaluated as follows.

- The growth of the second leaf is inhibited, and an inhibition circle is formed around the paper disk 3.

±2 Although no inhibition circle was formed macroscopically, the effect of the drug was observed.

+: Growth of bacteria is not inhibited and no inhibition circle is formed.

(The following is a blank space) Test Example 2 Mildew resistance test for wood and wood materials Jelton and particle board (each 3 cm x 3 cm x O, 6 cm thick) were used as test pieces. Immerse for 3 minutes in the chemical solution of each composition shown in Table 5, -
Air-dried day and night.

PDA medium 15- was dispensed into a petri dish, and after solidification, a sterilized polypropylene net was placed, and a drug-treated test piece was placed on top of it.

Aspergillus ni
ger), Penicillum citrinum (Penicillum citrinum)
umn citrinum), Rhizopus nigricans (
Rhizopus nigricans), Trichoderma virida
e) and Alternaria citri
A citri) mixed spore solution was sprayed uniformly onto the test piece for 2 days, and the test piece was stored at 28°C for 4 hours, and the state of mold growth was observed.

The number of repetitions of each test piece was three. The evaluation was as follows.

(Evaluation value) 0 No mold growth was observed on the test specimen.

1 Mold growth is observed only on the sides of the test specimen.

2. Mold growth is observed on 1/3 or less of the upper surface of the test piece.

3 Mold growth is observed on 1/3 or more of the upper surface of the test specimen.

(The following is a blank space) Test Example 3 Anti-mold test of emulsion paint A paint was prepared by adding 1 part of each of the chemicals of Example 3 to 99 parts of biruniacetate-based emulsion paint.

The mold resistance test is based on J I 5-Z-2911r mold resistance test method, 7. The tests were carried out in accordance with the section on paint tests.

Table 6 Concentration A, 1 Mold pharmacomagnetism for one week (%) Occurrence status 3 a
0.2 No mold growth 3 b
O,2 No mold growth 3c o,24
No mold growth 3 d O, 24 No mold growth 3 e O, 24 No mold growth 3 f
0.24 No mold 3 g
0.2 Mold grows on 1/3 of the specimen area
The growth of 3h O,2 mold, which accounted for more than 173% of the specimen area.
3 i 0.24 Mold occupied more than 1/3 of the specimen area 3 j 0.2 Mold occupied more than 1/3 of the specimen area 3 k 0.2 Mold growth occupied 1/3 or more of the sample area 3 1 0.2 No treatment Mold growth occupied 173 or more of the sample area Mold growth occupied the entire surface of the sample.

Test Example 4 Test on Wood Decay Fungi
lus versicolor) and the brown rot fungus Tyromyces palustris.
) was tested.

The test method is painting, spraying,
The test method was based on the preservative efficacy test method for wood preservatives for dipping. In addition,
For evaluation, the weight loss rate of untreated and treated test materials was determined, and the efficacy value of the drug was calculated as follows.

Efficacy value = (UWL-TWL)/UWLX100UWL
: Average weight reduction rate (%) of untreated specimen TWL : Average weight reduction rate (%) of treated specimen (margin below)

Claims (1)

[Claims] 1, (A) at least one 4-alkoxy-2,5,6-trifluoroisophthalonitrile compound and (B
) 2-benzimidazole methylcarbamate, 2-(
An antibacterial composition containing as an active ingredient at least one compound selected from 4-thiazolyl)benzimidazole and 1-butylcarbamoyl-2-benzimidazole methyl carbamate.