JPS6338966B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula (In the formula, X represents a halogen atom, a halo-lower alkyl group, or a lower alkyl group, R represents a hydrogen atom or an acetyl group, and R' represents a lower alkyl group, a lower alkoxy group, or a lower alkenyloxy group.) The present invention relates to a wood preservative and fungicide characterized by containing one or more 2-substituted benzanilide compounds and tetrachloroisophthalonitrile. In recent years, the demand for wood in Japan has increased significantly, and domestic wood resources have been depleted, and the current situation is that domestic production alone cannot meet the demand and we have no choice but to rely on imports from abroad. Domestic cypress and cedar, which have traditionally been used as building materials, have been resistant to microorganisms such as mold and fungi that weaken wood materials, even in Japan's relatively hot and humid climate.
However, rice, toga, lauan, red pine, etc. imported from overseas are highly susceptible to mold and bacteria, so they are specially treated with chemicals and used as building materials. In addition, recently, the architectural style of houses has changed and energy conservation measures are being taken, and while heat-retaining buildings are becoming more important, measures against humidity have become neglected, and in cold regions, an unprecedented problem of wood deterioration due to bacteria has arisen. Conventionally, creosote oil, inorganic fluorides, phenolic compounds, copper, chromium, arsenic compounds, organic tin compounds, etc. have been used as wood preservatives and fungicides in this regard, but they have at least been used to prevent human and livestock diseases including rashes. However, they have some disadvantages, such as toxicity to wood, contamination of the wood such as coloring, pollution from the perspective of environmental pollution, control costs, and efficacy. Therefore, there is a strong desire for a safe wood preservative and fungicide that is excellent in its preservative and antifungal effect, is inexpensive, and does not cause pollution, but it has not been possible to obtain an agent that meets the purpose. In view of the above, the present inventors conducted extensive research on preventing wood deterioration caused by wood-decaying fungi and various molds. As a result, the present inventors developed a composition of the present invention which is a combination of one or more 2-substituted benzanilide compounds and tetrachloroisophthalonitrile. The drug has extremely superior effects compared to using each drug alone,
Furthermore, the present invention was completed based on the discovery that it is a safe drug with low toxicity and no risk of causing pollution. The 2-substituted benzanilide compound, which is one component of the present invention, is disclosed in Japanese Patent Publication No. 52-37048 and Japanese Patent Publication No. 53-14617.
Tetrachloroisophthalonitrile is also a fungicide known from Japanese Patent Application Laid-open No. 141117-1983. When these agents are used alone as wood preservatives and fungicides, they are less effective against basidiomycetes and filamentous fungi, which are the main causes of wood deterioration, and high doses must be used to achieve full effect. It was a chemical that could not be used as a wood preservative or fungicide. However, the preservative and fungicide of the present invention exhibits a synergistic effect when mixed, which cannot be expected when used alone. It effectively controls basidiomycetes and filamentous fungi at low doses, and is safer than conventional metal-containing doses. Examples of the 2-substituted benzanilide compounds of the above general formula used in the present invention include the following. These compounds can be used in combination. Compound 1

【formula】 (white needle-like crystals) m.p154-155℃) Compound 2

【formula】 (White scaly crystals m.p.94-96℃) Compound 3

【formula】 (White needle-like crystals m.p.79-80℃) Compound 4

【formula】 (White needle-like crystals m.p.105-106℃) Compound 5

【formula】 (White prismatic crystal m.p.76-78℃) Compound 6

【formula】 (colorless scaly crystals m.p.105-106℃) Compound 7

【formula】 (Colorless prismatic crystal m.p.52-57℃) Compound 8

【formula】 (White needle-like crystals m.p.153-155℃) Compound 9

【formula】 (Colorless prismatic crystal m.p.60-62℃) compound 10

【formula】 (White prismatic crystal m.p.142-143℃) compound 11

【formula】 (Pink transparent liquid b.p.148℃/0.04mmHg) compound 12

【formula】 (White needle-like crystals m.p.115-116℃) compound 13

[Formula] (White needle-like crystals mp92-93℃) Compound 14 (White powder crystal mp85-89℃) The blending ratio of the 2-substituted benzanilide compound and tetrachloroisophthalonitrile can vary over a wide range depending on the purpose of use, but the 2-
When one or more substituted benzanilide compounds and tetrachloroisophthalonitrile are blended in a weight ratio of 1 to 0.1 to 10 for the former, it exhibits a synergistic effect against wood-decaying fungi and filamentous fungi. be. The agent according to the present invention can be formulated into an emulsion, oil, wettable powder, sol, etc. by adding a suitable diluent or emulsifier, and can be prepared using conventional wood preservative and fungicide treatment methods such as dipping, spraying, and coating. , diffusion method with high concentration chemical solution, and pressurization method. It is also possible to treat plywood and fiberboard with the chemical by mixing it with adhesives and the like. In addition, the agent of the present invention can be used in combination with insecticides and insect repellents, and it has often been found that the insect repellent effect is improved without adversely affecting the effects of other agents. Next, formulation examples will be explained. Formulation Example 1 (Emulsion) Compound (1) 4.5%, tetrachloroisophthalonitrile 4.5%, activator Solpol 800A (product of Toho Chemical Industry Co., Ltd.) 5%, and 1,2,4-trimethylbenzene 86% were uniformly added. Dissolve and make an emulsion. Formulation Example 2 (Emulsion) Compound (2) 9%, tetrachloroisophthalonitrile 1%, surfactant Solpol 800A (product of Toho Chemical Industry Co., Ltd.) 5%, and 1,2,4-trimethylbenzene 85% were uniformly mixed. Dissolve in to make an emulsion. Formulation Example 3 (Emulsion) Compound (6) 3%, tetrachloroisophthalonitrile 7%, surfactant Solpol 800A (product of Toho Chemical Industry Co., Ltd.) 5%, and 1,2,4-trimethylbenzene 85% were uniformly mixed. Dissolve in to make an emulsion. Formulation Example 4 (Emulsion) Compound (7) 6%, tetrachloroisophthalonitrile 7%, surfactant Solpol 800A (product of Toho Chemical Industry Co., Ltd.) 5%, 1,2,4-trimethylbenzene 50%, xylene Uniformly dissolve 35% and make an emulsion. Formulation Example 5 (Emulsion) Compound (13) 3%, tetrachloroisophthalonitrile 5%, surfactant Solpol 800A (product of Toho Chemical Industry Co., Ltd.) 5%, mp-cresol 1%, ortho-xylene 30%, 1 , 56% of 2,4-methoxybutanol are uniformly dissolved to form an emulsion. Formulation example 6 (hydrating powder) Compound (3) 15%, tetrachloroisophthalonitrile 15%, surfactant Neopellex powder (Kao Soap Co., Ltd. product) 2%, Sunextract P-552 (Sanyo Kokusaku Pulp) Co., Ltd. product) 2%, Carplex #80 3
%, and 63% of a mixture of giclite and clay were mixed and pulverized using a Jet-O-Mizer mill to form a wettable powder. Formulation Example 7 (Oil agent) Compound (4) 1%, tetrachloroisophthalonitrile 3%, Hysol #100 (Nippon Oil Co., Ltd. product) 50
%, 46% kerosene is uniformly dissolved to form an oil agent. Formulation Example 8 (Oil agent) Compound (13) 2%, Tetrachloroisophthalonitrile 1%, Solpol 800A (Toho Chemical Co., Ltd. product) 1%, Hysol #100 (Nippon Oil product) 96%
Dissolve it uniformly and use it as an oil solution. Formulation Example 9 (Sol) Compound (14) 10%, Tetrachloroisophthalonitrile 10%, Carboxyl Methyl Cellulose 2
%, sodium dodecylbenzenesulfonate 2
%, glycerin 15%, ethylene glycol 15%,
Add 46% water and use a wet grinding mixer to obtain a sol. Next, the effects of the wood preservative and fungicidal agent of the present invention will be specifically explained with reference to test examples. Test Example 1 (Minimum complete killing concentration test against harmful microorganisms) A potato culture medium containing a predetermined concentration of an emulsion prepared at an active ingredient ratio of 1:1 according to Formulation Example 1 is solidified in a Shearley. On this flat surface, fungi of the test harmful microorganisms are inoculated, cultured for 6 days in a thermostat at 28°C, and the elongation of the hyphae is investigated to determine the minimum concentration (ppm) that completely kills the hyphae by the drug. The results are shown in Table 1.

【table】

[Table] Test example 2 (Minimum complete killing concentration test against harmful microorganisms) Trichoderma SP, which is a harmful microorganism to wood,
The minimum concentration of a mixture of compound (2) or (13) and tetrachloroisophthalonitrile to completely kill mycelium was determined using the test method of Example 1 using M. chinensis and C. versicolor. The test drugs were formulated according to Formulation Examples 2 and 3. The results are shown in Table 2-1 and Table 2-2.

【table】

[Table] Test Example 3 (Wood preservative effect test) (1) Test piece of wood: cedar end side 20mm x 20mm x height
10mm Moisture content 7% (2) Test chemical: Chemical prepared according to Formulation Example 3 (3) Chemical treatment method for wood: Inject under reduced pressure using the apparatus shown in Figure 1 in accordance with JIS-A-9301. By evacuating the inside of the desiccator using a vacuum pump and opening the container, the sample flows into the beaker and is absorbed by the wood chips under reduced pressure. The absorption amount at this time is 250±10% of the weight of the wood piece. (4) Weatherproofing and antibacterial operations: According to JIS-A-9302. (5) Weatherproofing operation: Put the treated wood chips into a beaker,
Wash with water for 1 hour at a water flow rate of 1 to 2 minutes and a water temperature of 25±3°C. Then 22-23 at 60℃
Allow time to volatilize and repeat this operation to complete the weathering operation. (6) Antibacterial operation: base area 50~100cm, total capacity 500~
Put 350 g of sea sand into an 800 ml cylindrical wide-mouth glass bottle, sterilize it with dry heat, and add the culture solution (composition: 4% glucose, 0.3% peptone, 15% poisonous bud extract).
Add 100ml. As a decaying fungus, St.
After inoculating C. versicolor and culturing it for 4 days to propagate the test bacteria, a glass rod is placed on top and a piece of treated wood is placed on top. After culturing for 90 days at a temperature of 28°C and a relative concentration of 75%, the weight change of the wood pieces is investigated. The potency value of the active compound is determined by determining the percentage weight loss. Weight reduction rate (%) = Weight before antibacterial operation - Weight after antibacterial operation / Weight before antibacterial operation x 100 Effective amount = 100 - Weight reduction rate The results are shown in Table 3.

[Table] As is clear from Table 3 above, it has been found that the drug according to the present invention maintains effects and properties comparable to those of arsenic and chromium compounds.

[Brief explanation of drawings]

The figure is a diagram of the treated test specimen preparation apparatus used in the wood preservative effect test in Example 3. In the figure, the symbol indicates a vacuum gauge, A is a vacuum gauge, B is a vacuum pump, C is a pinch pot, D is a three-way pot, and E is a three-sided pot. F is a beaker, G is a piece of wood, H is gold, I is a vacuum dessicator, J is a sample, K is a thermometer, and L is a stand.

Claims (1)

[Claims] 1. General formula (In the formula, X represents a halogen atom, a halo-lower alkyl group, or a lower alkyl group, R represents a hydrogen atom or an acetyl group, and R' represents a lower alkyl group, a lower alkoxy group, or a lower alkenyloxy group.) 1 of 2-substituted benzanilide compounds
A wood preservative and fungicide characterized by containing at least one species and tetrachloroisophthalonitrile.