JPS5810362B2 - Satsukinzai - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention uses the general formula (in the formula, ↓ is alkyl having 4 to 8 carbon atoms, R1 is nitro substituted at the 4- or 5-position, R2 is lower alkyl, allyl) as an active ingredient. , cyclohexyl, phenyl.

) The present invention relates to a disinfectant characterized by containing one or more kinds of novel salicylanilide hydrobamate ester derivatives represented by the following formulas.

Conventionally, salicylanilide derivatives (substituted with halogens, nitriles, etc.) have been used as fungicides,
Useful as insecticides are described, for example, in U.S. Pat.
It is known from specification No. 583.

As a result of extensive studies on compounds useful as bactericidal agents, the present inventors have found that a novel salicylanilide tribamate ester derivative represented by the general formula CI) has excellent antibacterial activity against microorganisms, especially bacteria. I found out.

Furthermore, since it is non-metallic, it has almost no toxicity to mammals, and does not irritate the skin at practical concentrations, so it is also important as an agent for eradicating harmful microorganisms.

For example, among the compounds of the general formula [I], the LD5o of 5-tert-butyl-2-methyl-4'-nitrosalicylanilite phenyl-rubamate is 1o in mice.
It is 9 or more in ooo~/.

The disinfectant of the present invention, which has such excellent antibacterial activity and is considerably less toxic to humans and animals, can be used as an industrial preservative and disinfectant, for example, in paints, textile products, synthetic resin products, etc.
It can be used for leather, etc.

It also has the effect of preventing the formation of slime that occurs during the manufacturing process in the pulp and paper industry.

Furthermore, it can be incorporated into cosmetic cleansing compositions to maintain antimicrobial activity.

The fungicide of the present invention can be prepared by mixing one or more compounds of the general formula [■] with one or more other fungicides as necessary and adding it directly depending on the purpose of use, or by adding it directly to an appropriate liquid. dissolve or
or dispersed or mixed with or adsorbed with suitable solids, emulsifiers, dispersants,
Suspending agents, spreading agents, penetrating agents, seminal plasma agents, stabilizers, etc. are added to the formulations, such as oil solutions, emulsions, wettable powders, tablets, and sprays.

The compound of the general formula [■] can be produced, for example, by reacting a compound represented by the general formula with a compound represented by the general formula.

That is, a compound represented by the general formula (ID and (II)) is optionally prepared in the presence of a catalyst (a basic catalyst such as triethylamine, pyridine, or triethylenediamine),
It is produced by reacting in an inert solvent or without a solvent.

The salicylanilide derivative of the general formula [■] used in the present invention is produced from 5-alkyl salicylic acid and substituted aniline by the method of producing acid amide.

Further, as the incyanate of general formula (m), any commonly used isocyanate can be used.

Production Example 5 - Tertiary-butyl-2'-methyl-4'-nitrosalicylanilide phenylcarbamate ester 5-tertiary-butyl-2'-methyl-47-nidrosalicylanilide 32.8 P When 0.3 ml of triethylamine is added to 150 g of phenyl isocyanate while stirring at 25°C, a homogeneous solution is generated while generating heat, and crystals are precipitated after 10 minutes.

Cool in water for 30 minutes, and sieve.

When washed with toluene and recrystallized with acetone, the melting point is 173 ~
The title compound (compound 1) 30r is obtained as white crystals at 175°C.

Examples of compounds obtained in the same manner are shown below, but it goes without saying that the compounds used in the present invention are not limited to these.

◎5-Tertiary butyl-2-methyl-4'-nitrosalicylanilide allyl rubbermate ester (compound 2)
Melting point: 152-153℃ White crystals ◎5-Tertiary butyl-2
Methyl-4'-nitrosalicylanilide methylcarbamate (Compound 3) Melting point: 148-150℃ White crystals Compound 4) Melting point: 134-136.5°C White crystals ◎ 5-Tertiary butyl-2-methyl-47-nitrosalicylanidide ethylcarbamate ester (Compound 5) Melting point: 147.
5-149℃ White crystals ◎5-tertiary butyl-! -Methyl-4'-nitrosalicylanilide provil rubamate ester (compound 6) Melting point 134.5-136.5°C
White crystals ◎ 5-Tertiary butyl-2'-methyl- 4'-nitrosalicylanilide isoglobil rubamate ester (compound 7) Melting point 156-157°C White crystals ◎ 5-Tertiary butyl-2'-methyl- 4'-nitrosalicylanilide butyl rubbermate ester (compound 8
) Melting point: 142-144℃ White crystals ◎5-Tertiary amyl-
2-Methyl-5'-nitrosalicylanilide methylrubamate ester (compound 9) Melting point 142-145°C
White crystals ◎ 5-Tertiary amyl-2'-methyl-5'-nitrosalicylanilide phenylcarbamate ester (Compound 10) Melting point 155-157.5℃ White crystals ◎ 5-Tertiary octyl-2-methyl -57-nitrosalicylanilide methylcarbamate (compound 1)
1) Melting point: 169.5-171.5℃ White crystals
Compound 12) Melting point: 163-165°C White crystals ◎ 5-Tertiary amyl-2-methyl-4-nitrosalicylanilide methyl rubamate ester (Compound 13)
Melting point: 136-139°C Pale yellow crystals ◎ 5-Second-butyl-2'-methyl-47-nidrosalicylanilide methylcarbamate ester (Compound 1
4) White crystals with melting point of 124 to 126°C The present invention will be specifically explained below with reference to Examples.

Example 1 A compound of the general formula [■] is mixed into an ordinary agar medium at a constant concentration and allowed to solidify.

This is inoculated with Staphylococcus aureus and Bacillus subtilis as test bacteria, cultured at 37°C for 2 days, and the minimum inhibitory concentration (MIC) is determined.

Units are shown in ppm.

Compound A: 47-acetylsalicylanilide methylcarbamate (compound described in U.S. Pat. No. 3,288,844) Compound B: 47-diatsusalicylanilide methylcarbamate (compound described in U.S. Pat. No. 3,317,583) ) Example 2 Compound 1 was added to a cleaning solution containing 2.02 parts of sodium soap per 11'. Add so that it becomes /l.

A circular white cloth with a diameter of 30 mm was immersed in this solution and heated at 80°C for 3
The sample is treated for 0 minutes, washed under running water (11 minutes) for 30 minutes, dehydrated by centrifugation, and then dried with an iron.

This is placed on a regular agar medium that has been previously inoculated with Staphylococcus aureus and cultured at 37°C for 24 hours, and further cultured at 37°C for 24 hours.

No bacterial growth was observed on the circular cloth treated with Compound 1, and no bacterial growth was observed around the circular cloth.

Example 3 Compound 4 was mixed with polyethylene resin at a concentration of 1.0%, and a foil having a thickness of 0.5 mm and a diameter of 30 mm was produced at 200° C. by injection molding.

When this foil was treated in the same manner as in Example 2, no growth of Staphylococcus aureus was observed on this foil, and no growth was observed around the medium.

Claims (1)

[Scope of Claims] 1. A disinfectant characterized by containing one or more kinds of novel salicylanilide hydrorubamate ester derivatives represented by the general formula as an active ingredient. (In the formula, R is alkyl having 4 to 8 carbon atoms, R1 is nitro substituted at the 4th or 5th position, R2 is lower alkyl,
Indicates allyl, cyclohexyl, and phenyl. )