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Microbicide

A technology of microbicides and hydrolyzates, applied in the directions of biocides, animal repellents, plant growth regulators, etc., can solve the problems of improving the performance of few microbicides, and achieve the effect of reducing the residual amount of acetic acid and reducing TOC

Active Publication Date: 2014-05-14
KURITA WATER INDUSTRIES LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, improvement in the performance of microbicides themselves has rarely been addressed as a problem in the past, and it is known that compounds having a 3-isothiazolone ring have a low volatile content and are used to prevent air pollution caused by coating agents or adhesives. However, its use as a slimicicide is not known to the public

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Production of 5-chloro-2-methyl-4-isothiazolin-3-one

[0072] N,N'-dimethyl-3,3'-dithiodipropionamide (150 g, 0.54 mol, moisture content 0.1 wt %) was diluted with 800 g of ethyl acetate having a moisture content of 0.05 wt %, Chlorine gas with a water content of 0.001% by weight was blown in to react, and ethyl acetate slurry of 5-chloro-2-methyl-4-isothiazolin-3-one hydrochloride was obtained.

[0073]The obtained slurry was filtered, the obtained wet filter cake was washed with toluene having a water content of 0.05% by weight, and the ethyl acetate solvent was exchanged for toluene. Dissolve 200 g of the obtained crystalline 5-chloro-2-methyl-4-isothiazoline-3-one chlorate in water, add magnesium nitrate hexahydrate, magnesium oxide, and hydrochloric acid to adjust the pH to 1-4, and obtain aqueous solution. The obtained aqueous solution was concentrated under reduced pressure at 40 to 80° C. for 3 hours, cooled to room temperature, and then naturally filtered to ...

Embodiment 2

[0088] Production of 5-chloro-2-methyl-4-isothiazolin-3-one

[0089] The intended product was obtained in the same manner as in Example 1, except that butyl acetate having a water content of 0.05% by weight was used instead of ethyl acetate having a water content of 0.05% by weight as a solvent in the chlorination reaction.

[0090] Using the obtained 5-chloro-2-methyl-4-isothiazoline-3-one, adopt the same method as in Example 1 to prepare 5-chloro-2-methyl-4-isothiazoline-3- A 10% by weight aqueous solution of ketones was quantified in the same manner as in Example 1 for residual organic matter and its hydrolyzate. The results are shown in Table 1.

Embodiment 3

[0104] Embodiment 3, comparative example 1, 2

[0105] TOC reduction effect of permeated water in RO membrane module

[0106] A 10% by weight aqueous solution of 5-chloro-2-methyl-4-isothiazolin-3-one produced in Example 1 and Comparative Synthesis Examples 1 and 2 was used as a slimicide. For the RO membrane, a 4-inch module of BW-10 manufactured by DOW was used, and the operating pressure was adjusted to 1.5 Mpa. The feed water in the RO membrane module uses dechlorinated water permeated with activated carbon. The residual free chlorine concentration of the dechlorinated water was confirmed to be 0 by the DPD method. The slimicide was added so that the concentration of 5-chloro-2-methyl-4-isothiazolin-3-one in the supply water would be 0.15 mg / L. The TOC of the treated water permeated through the RO membrane module is measured. Table 2 shows the results (ppb).

[0107] Table 2

[0108]

[0109] As can be seen from Table 1, compared with existing products, the...

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PUM

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Abstract

Provided is a microbicide having 5-chloro-2-methyl-4-isothiazolin-3-one as the active component and a reduced amount of residual materials and hydrolysates from the organic solvents used in the industrial manufacturing method thereof. The microbicide, which includes 5-chloro-2-methyl-4-isothiazolin-3-one as the active component and has a total amount of the organic solvent and the hydrolysate thereof of no more than 200ppm when the concentration of the active component is 10 wt%, is obtained by a manufacturing method involving a process for the cyclization of sulfide amides and a process for neutralizing hydrogen halide salts of a compound comprising a 3-isothiazolone ring, wherein acetic acid ester containing no more than 0.1 wt% of water is used as the reacting solvent for the cyclization process, a hydrocarbon compound having a water content of no more than 0.1 wt% is added to the hydrogen halide salt obtained by filtering the acetic ester fluid dispersions of the hydrogen halide salt and the resulting mixture is filtered, solvents are exchanged, and the processes are carried out in an atmosphere with a water content of no more than 0.1%.

Description

technical field [0001] The present invention relates to a microbicide containing 5-chloro-2-methyl-4-isothiazolin-3-one as an active ingredient, and more specifically, relates to an organic solvent used in the production process of the active ingredient. Microbicides with reduced levels of residues and their hydrolysates. Background technique [0002] 5-Chloro-2-methyl-4-isothiazolin-3-one has the biological activity of inhibiting the proliferation of microorganisms, so it is used as a preservative or fungicide for various industrial products. In addition, it can also be used as an active ingredient of a slime control agent for preventing slime mold consisting of microorganisms such as bacteria or organic matter derived from algae generated in water treatment equipment or cooling water systems. [0003] Especially in water treatment equipment or cooling water systems, depending on the purpose of water treatment or the equipment form of the cooling water system (closed syste...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A01N43/80A01P1/00C02F1/50C07D275/02
CPCC02F2303/20A01N43/80B01D65/02B01D2321/168C02F2303/04C02F1/50C07D275/03C02F2103/023C02F1/441
Inventor 大西敏圣东条环肥塚安弘山西正人青木哲也冲野研二
Owner KURITA WATER INDUSTRIES LTD
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