JPS5810505A - Industrial bactericide - Google Patents

Abstract

NEW MATERIAL:The reaction product of 1,2-benzisothiazolin-3-one with the azalactam compound of formulaI(R<1> is 12-16C alkyl or hydroxyalkyl; R<2> is 1-3C alkyl). EXAMPLE:4-Tetradecylaminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one salt of 1,2-benzisothiazolin-3-one of formula II. USE:An industrial bactericide. It has synergistic bactericidal activity especially to Aerobacter aerogenes, keeping the antibacterial spectra of the components. PROCESS:The objective compound is prepared by reacting 1,2-benzisothiazoline- 3-one with an azalactam compound of formulaIin methanol.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an industrial fungicide containing a novel azalactam compound salt of L2-benzisothiazolin-3-one as an active ingredient. The industrial disinfectant of the present invention maintains the antibacterial spectrum of the raw material components and provides a complementary effect of antibacterial action.

1 and 2, which are one of the compounds constituting the active ingredient of the present invention
- Benzisothiazolin-3-one is an effective agent for preventing spoilage of art paper, coated paper coating cuffs, emulsion paints, latex, synthetic resin emulsions, cutting fluids, adhesive starch pastes, pigment slurries, and water-based industrial materials. It has been designated as Tenkawa. Furthermore, in order to improve the solubility of L2-benzinthiazolin-3-one in water, it has been proposed to convert this product into an amine salt (see Japanese Patent Publication No. 10612/1983).

In addition, the other compound is a compound of the general formula (wherein R1 represents an alkyl group or a hydroxyalkyl group of C--, and R represents an alkyl group of C--).

) is known to have activity against microorganisms, and it has been suggested that it may be used as a fungicide for medical, agricultural, and industrial purposes (Kagaku Keizai 1.1980 Hayabusa). December issue, 49-st, g). By the way, L2-benzisothiazolin-3-one has strong bacteriostatic activity, but weak bactericidal activity, and it is also effective against pseudomonas.
It also has the drawback of being weakly effective against S. aeruginosa (this bacterium is one of the main causes of microbial contamination of aqueous industrial materials), and the occurrence of resistant sagebrush has become a problem.

The azotectam compound represented by the general formula (I) is a compound with strong bacteriostatic and antibacterial properties, but it is also a compound that has strong bacteriostatic and antibacterial properties. ) has a weak defect that is uniquely weak against K. The compound of general formula (I) also has problems when used alone as an industrial fungicide due to its non-uniform antibacterial spectrum.

As a result of intensive research into compounds that complement the drawbacks of each of the above compounds, the present inventors found that 1.2
- A compound which is a novel amine salt of 1,2-benzisothiazolin-3-one obtained by reacting benzisothiazolin-3-one' with an azolactam compound treated with monodisperse formula (I) is This led to the completion of the present invention based on the new finding that not only does the plant have a complementary effect on the aerobacterium, but also a complementary effect on the aerobacterium aerogenes.

Examples of the azalactam compounds used in the present invention include the following compounds. 4-dodecylaminoethyl-7-methyl-3,6-sihydro 2H-L4
-Diazepin-5-one, 4-tetocdecylaminoethyl-7-methyl-λ6-sihydro2H-L4-diazepin-5-one, 4-hexadecylaminoethyl-7-
Methyl-λ6-sihydro-2H-L4-diazepine-5
-one, 4-C2-C2-hydroxytetradecylamino)ethyl]-7-methyl-λ6-sihydro2■-L
4-Diazepin-5-one, 4-tetocdecylaminoethyl-ethyl-λ6-sihydro 2H-14-diazepin-5-one, 4-tetocudecylaminoethyl-normalprobyl-λ6-sihydro 2H-1,4 −
diazepin-5-one and the like.

In actual use, the solvent is not particularly limited and may be changed depending on the intended use, but for example, water or a hydrophilic organic solvent (for example, dimethylformamide F) may be used.
After dissolving the compound of the present invention in 1 ethylene glycol, methyl cellosolve, methyl calpitol, methanol, ethanol, dimethyl sulfoxide, etc.), the growth of microorganisms is prevented by adding a drug solution to the system. Is possible. Note that an antifoaming agent may be added if necessary.

The compounds of the present invention can be used not only in the above-mentioned applications, but also in the water systems of cooling towers in paper mills, the drainage systems of air conditioning equipment in vehicles, aircraft, ships, buildings, etc., the slime in spring water systems of tunnels, and civil engineering construction work. It is also used for the purpose of preventing rot in muddy water construction methods.

EXAMPLES The present invention will be explained in more detail with reference to Examples below.

Example 1 (Production Example) 30.2 g of L2-benzisothiazolin-3-one and 4
-tetradecylaminoethyl-7-methyl-3,6-sihydro-2H-1,4-diazepin-5-one (hereinafter T
It is called AE-CI. )36.6g and methanol SO
Dissolve at 50-60'C in the presence of d. Thereafter, methanol is distilled off to obtain a brown viscous TAΣ-CH salt of 1,2-benzisothiazolin-3-one. This compound does not crystallize even when cooled to -10°C.

In addition, the ultraviolet absorption spectrum was measured and 'I'AE-CI was determined.
Disappearance of absorption at 2 g 7 nu, which is the characteristic absorption of , was confirmed. The pH of a 0.1% aqueous solution of this compound was 7.5.

note)! Structural formula % formula % () -1,4-diazepin-5-one (hereinafter referred to as IIITAI
-CH. ) 38.1 g and methanol 50
- at 50-60°C. After dissolution, methanol is distilled off to obtain a brown viscous HTAK-CH salt of 2-benzisothiazolin-3-one. This compound does not crystallize even when cooled to -1θ°C. Furthermore, the ultraviolet absorption spectrum was measured to confirm that the absorption of HTAK-CIII at 275 nm disappeared. 0 of this compound
．． The pH of the 1% aqueous solution is 6.8.

Note) Structural formula of HTAK-CI % Formula % () 30 g of the salt obtained in Example 1 was mixed with 70 g of methylcarpitol.
A preparation is prepared by dissolving K.

The active ingredient in the formulation is not limited to this concentration.

The suitable solvent is not particularly limited, and may be changed depending on the intended use, and an antifoaming agent may be added if necessary.

Example 4 (formulation example) 30 g of the salt obtained in Example 2 was mixed with methylcarpitol? The preparation is prepared by dissolving it in Og.

The active ingredient in the formulation is not limited to kernel concentration.

Further, the solvent is not particularly limited, and may be changed depending on the intended use, and an antifoaming agent may be added if necessary.

Example 5 (Test Example) In advance, test bacteria were placed in a bouillon medium with a pH of 7 to
Preculture (shaking culture) for 18 hours. activated liquid 0
．． 1d into a new broth medium IO strain. Add each chemical solution to it to a predetermined concentration (chemical solutions are
Dilute with water or a hydrophilic Iag medium to determine the number of axes in advance. ).

After sowing, the seeds are boiled and cultured at 37°C. After 6.5 hours, MIC (j [1 small inhibitory concentration) ft is determined. The rice supplied is shown in Table 1.

-Leave blank below Example 6 (Test example) A certain paper factory! II! A lot of slime is generated in certain processes at the construction site, giving off a foul odor. The white water from this process was sampled, and the slime-forming bacteria in the white water were grown on a bouillon agar slope. The following test was conducted using the slime-forming wild strain.

First, in advance, this slime-forming bacteria was grown in bouillon medium for 15 to 30 minutes.
Preincubate for 18 hours and activate.

Add 0.1% of the bacterial solution to 10wt of sterile water, and add the following drug to 100pP! Add to IK. Immediately after addition, the mixture is shaken at 37'C, and the number of surviving bacteria is measured over time by the plate dilution method. The results are shown in Table 2.

(Test drug) A drug solution prepared by dissolving 10 g of 1,1,2-benzisothiazolin-3-one in 90 g of methylcarpitol.

L TAE-CHlog with 90g of methylcarpitol
A chemical solution dissolved in

3. E[TAE-CHlog to ethyl alcohol 9
A drug solution dissolved in 0g.

L A drug solution obtained by diluting the formulation of Example 3 three times with methylcarpitol.

S, drug solution obtained by diluting the formulation of Example 4 three times with methylcarpitol.

Claims (1)

[Claims] L2-benzinthiazolin-3-one and the general formula (wherein R1 is CIQ~, 6 alkyl group or human o
12 represents the alkyl group of cIN3. ) An industrial fungicide characterized by containing a reaction product with an azolactam compound represented by the following as an active ingredient.