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Five unconventional facts about isothiazolinones that cannot be learned from books

2023-04-11

1、What are isoxazolines?

Isazolones (sometimes isazolones) are organic compounds with the formula (CH)2SN(H)CO. It is a white solid that is structurally related to isoxazoles. Although trazodone itself is of limited interest, some of its derivatives are widely used as preservatives and antimicrobial agents.

2. How to do isoxazolines?

Compared to many other simple heterocycles, isothiazolinone was discovered relatively late, appearing as early as reported in the 1960s.

Isothiazolinones can be prepared on an industrial scale by ring closure of 3-yl propionamide. These compounds are produced from acrylic acid.

Isothiazolinones

Ring closure of thioamides is usually achieved by chlorination or by oxidation of the 3-yl amide to the corresponding disulfide.

In addition to this, many other production methods have been studied, including thiocyanates to propargylamides.

Isothiazolinones

3. The main application scenarios of isoxazolines.

The antibacterial activity of isoxazoline is attributed to the ability to inhibit life-sustaining enzymes. In particular, enzymes with thiols in the active site. Currently, isoxazolines are determined to form mixed disulfides when dealing with such species.
Major isoxazolines.

All these compounds have antimicrobial properties. They are used to control bacteria, fungi, and algae in cooling water systems, combustion storage tanks, pulp and paper mill water systems, oil extraction systems, wood preservation, and some coatings. They are antifouling agents. They are commonly used in shampoos and other hair care products.



Chlormetazolone (CMIT) and 2-metaxalone-3-one are commonly used derivatives. A 3:1 mixture of CMIT: MIT is sold as Kathon. Lathon is supplied as a concentrated solution containing 1.5-15% CMIT/MIT. In applications, the recommended level of use is six ppm to 75 ppm of active isazolone.

4,5-Dichloro-2-octyl-4-isothiazolinone-3-one (DCOI or Sea-Nine 211) is mainly used as an antifouling agent, i.e., for coating the hull of ships to prevent the formation of barnacles, etc.

The observed pronounced biological effects of isozole-containing compounds have led to an interest in drug discovery and development programs for this scaffold, an increase in the number of related patent applications, and the successful introduction of isozole-based derivatives to the market. Among industrial applications and active intermediates, the most widespread synthesis of various organic compounds, including drugs and agrochemicals, are derivatives based on isazolone-3-ketones.

Known for its remarkable antifungal and antibacterial properties, isoxazoline 3-one is widely used as a bactericide in various industrial water treatment applications to control microbial growth and biofouling. It is also recommended as a preservative to prevent fungal growth in emulsion paints, wood varnishes, adhesives, natural and artificial leathers, and many other products. The most common isazolones used in commercial applications, alone or in combination, are methylisazolone (MI), methylchloroisazolone (MCI), benzylisazolone (BIT), octylisazolone (OIT), and dichloroisazolone (DCOIT) (Figure 1). Methylisozolone is commonly used in wastewater treatment technology, cosmetics, coatings, and detergents combined with MCI (in a ratio of 3:1) as the active ingredient in the commercial biocide Kathon. BIT and OIT are banned for use in cosmetics but are commonly used in cleaning and leather products as antifouling coating agents, respectively. The biocidal ingredient DCOIT in SeaNine 211 is a widely used antifouling agent that can stop the phenomenon of undesirable biological contamination.

4、The application characteristics of isoxazoline in water treatment.

·Trazodone has a strong inhibitory and bactericidal effect on common bacteria, fungi, and algae. And there are many advantages. For example, high bactericidal efficiency, useful decomposition, no residue, safe operation, good compatibility, good stability, low operating cost, etc.

·Trazodone can be mixed with chlorine and most cationic, anionic, and nonionic surfactants. When used in large quantities, its biological sludge stripping effect is good.

·Trazodone fungicides are broad-spectrum, high-efficiency, low-toxicity, and non-oxidizing, which are ideal fungicides in China. It is the perfect biocide in the industrial circulating cooling water system. It can also be used in sewage treatment, oil fields, paper making, pesticides, cutting oil, leather, detergent, cosmetics, and other areas.

·Trazodone has a high inhibitory effect on various fungi and algae such as algae, brown algae, fungi, and bacteria. It can also control the growth of slime in water. Trazodone also affects the stripping, dispersion, and penetration of mucus. It protects water quality and ensures the regular operation of equipment.

·The performance of isoxazoline is very stable—high applicability. Just put a small amount of isazolone where water treatment is needed. And this fungicide is non-toxic. Will not cause adverse toxic effects on the water itself, can be used with confidence.

If you want to know more about Isothiazolinones or isothiazolone biocide, please contact us, or click Isothiazolinones, thanks!

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