64359-81-5

Usage

InChI:InChI=1/C11H17Cl2NOS/c1-2-3-4-5-6-7-8-14-11(15)9(12)10(13)16-14/h2-8H2,1H3

Synthetic route

3,3'-disulfanediylbis(N-octylpropanamide) (33312-01-5) → Sea-Nine 211 (64359-81-5)

Conditions	Yield
Stage #1: N,N'-dioctyl-3,3'-dithiodipropionamide With thionyl chloride In chloroform at 35℃; for 0.833333h; Stage #2: With chlorine In chloroform at 35℃; for 2h; Reagent/catalyst; Solvent; Temperature;	88.1%
With chlorine In chlorobenzene at 55 - 65℃; Temperature; Solvent; Flow reactor; Large scale;	1350 kg

3,3'-disulfanediylbis(N-octylpropanamide) (33312-01-5) → Sea-Nine 211 (64359-81-5) + 2-octyl-isothiazol-3-one (26530-20-1)

Conditions	Yield
Stage #1: N,N'-dioctyl-3,3'-dithiodipropionamide With sulfuryl dichloride for 9.5h; Stage #2: With chlorine at 40 - 45℃; for 15h;	A 56.5% B 19%

sulphur dichloride + acrylic acid octylamide (10124-68-2) → Sea-Nine 211 (64359-81-5)

Conditions	Yield
With triethylamine In chlorobenzene	22%

2-octyl-isothiazol-3-one (26530-20-1) → Sea-Nine 211 (64359-81-5)

Conditions	Yield
With sulfuryl dichloride In ethyl acetate at 70℃;
With chlorine at 40℃;

n-octyl 3-mercaptopropanamide → Sea-Nine 211 (64359-81-5) + 2-octyl-4-bromo-5-chloro-3-isothiazolone

Conditions	Yield
Stage #1: n-octyl 3-mercaptopropanamide With chlorine In 1,2-dichloro-ethane at 35 - 40℃; Inert atmosphere; Stage #2: With bromine In 1,2-dichloro-ethane

n-octyl 3-mercaptopropanamide → Sea-Nine 211 (64359-81-5)

Conditions	Yield
Stage #1: n-octyl 3-mercaptopropanamide With chlorine In chlorobenzene at 45 - 50℃; Flow reactor; Stage #2: With chlorine In chlorobenzene at 55 - 65℃; Flow reactor;	110 g

Sea-Nine 211 (64359-81-5) + 2-mercaptopyridine-1-oxide sodium salt (3811-73-2) → [4-chloro-2-(n-octyl)-3-isothiazolon-5-yl]-(1-oxypyridin-2-yl)sulfide

Conditions	Yield
With sodium hydroxide In ethanol; water for 4h; pH=8.5;	82%

Sea-Nine 211 (64359-81-5) + 2-mercaptopyridine-1-oxide sodium salt (3811-73-2) → [4-chloro-2-(n-octyl)-3-isothiazolon-5-yl]-(1-oxypyridin-2-yl)sulfide

Conditions	Yield
With sodium hydroxide In ethanol; dichloromethane	0.9 g (82%)

Sea-Nine 211 (64359-81-5) + zinc 5,10,15,20-tetrakis(4-methylphenyl)porphyrin (19414-67-6) → C48H36N4(2-)*C11H17Cl2NOS*Zn(2+)

Conditions	Yield
In methanol; water for 1h;	310 g

Upstream product

• 26530-20-1 2-octyl-isothiazol-3-one 
• 10124-68-2 acrylic acid octylamide 
• 33312-01-5 3,3'-disulfanediylbis(N-octylpropanamide) 

Relevant academic research and scientific papers

Method for coproducing OIT and DCOIT

The invention discloses a method for coproducing OIT and DCOIT. The method comprises the following steps: adding a raw material N, N'-di-n-octyldithiodipropionamide or N-n-octylmercaptopropionamide and a solvent into a chlorination reaction kettle, introducing chlorine, and carrying out solid-liquid separation on the material in the reaction kettle after the reaction is finished; distilling the obtained mother liquor under reduced pressure, and reserving kettle residues for later use; transferring the obtained filter cake to a neutralization kettle, adding a solvent and alkali liquor for neutralization and liquid separation to obtain an organic layer; carrying out water washing, desolventizing and filtering part on the organic layer to obtain the OIT finished product; carrying out azeotropic dehydration on the other part of the organic layer, combining with the kettle residues, introducing chlorine for chlorination, adding an alkali liquor into reaction liquid obtained after the reaction is finished for neutralization, and filtering; and recrystallizing the obtained filter cake, and leaching and drying the obtained solid to obtain the DCOIT finished product. According to the invention, the production efficiency is improved, the product quality is improved, and the method is an efficient and environment-friendly production method.

Preparation method of 4, 5-dichloro-2-n-octyl-3-isothiazolinone

The invention discloses a preparation method of 4, 5-dichloro-2-n-octyl-3-isothiazolinone. The preparation method comprises the following steps: 1) carrying out a reaction on dimethyl dithiodipropionate and n-octylamine to obtain 3, 3'-dithiodioctyl propionamide; and 2) carrying out a reaction on the 3, 3'-dithio dioctyl propionamide and phosphorus oxychloride, so as to obtain the 4, 5-dichloro-2-n-octyl-3-isothiazolinone. The preparation method of the 4, 5-dichloro-2-n-octyl-3-isothiazolinone provided by the invention is simple, impurities are not introduced in the process, the product purity is high, the production is environment-friendly and safe, and the market application prospect is wide.

Preparation method of 3-isothiazolinone compound

The invention discloses a preparation method of a 3-isothiazolinone compound, which comprises the following steps of adding raw materials and a solvent into a reaction system, and stirring and mixing,adding a dehydrating agent into the mixed solution, and stirring for reaction, introducing chlorine into the reaction system, stirring the reaction mixture for reaction, filtering and separating to obtain a product. According to the method, the chemical dehydrating agent is added into the reaction system to react with water or alcohol in the reaction system, so that water or alcohol in the systemis removed, side reaction caused by water or alcohol is avoided, the reaction yield is increased, and the economic benefit is remarkable.

A 4, 5 - dichloro - N - [...] thiazolinone preparation method

A preparation method of 4,5-dichloro-N-n-octyl isothiazolinone uses N,N- di-n-octyl-3,3-disulfide-di-propionamide as a raw material, and comprises the following steps: mixing N,N- di-n-octyl-3,3-disulfide-di-propionamide with a chloro solvent; adding a composite catalyst comprising metal chlorides, thiophene compounds and crown ether compounds; adding a chlorating agent at a low-temperature condition for closed-loop chlorination; carrying out separation and purification to obtain the 4,5-dichloro-N-n-octyl isothiazolinone. Tests show that the purity of the 4,5-dichloro-N-n-octyl isothiazolinone prepared according to the method can be higher than 98 percent; the product yield can be higher than 65 to 75 percent. Compared with the prior art, the method has the advantages that as the composite catalyst is adopted, the reaction time is short, the product cost is low, and the yield is high; the catalyst, the solvent as well as unreacted raw materials can be recycled, so that the requirements of environmental protection are met; the method is high in selectivity, mild in reaction, easy to control, stable in product quality, and high in yield, thereby being suitable for industrialized production.

Preparation method of 2-n-octyl-4-bromo-5-chloro-3-isothiazolone

The invention discloses a preparation method of 2-n-octyl-4-bromo-5-chloro-3-isothiazolone, and belongs to the technical field of organic chemistry. According to the preparation method, 3-mercapto-N-n-octylpropionamide, sulfonyl chloride, and bromine are taken as the raw materials, 1, 2-dichloroethane is taken as the solvent, the raw materials are heated to carry out chlorine cyclization and bromination reactions to generate a mixture composed of 2-n-octyl-4-bromo-5-chloro-3-isothiazolone, 2-n-octyl-4,5-dichloro-3-isothiazolone, and other impurities, then the mixture is subjected to recrystallization and column chromatography to obtain pure 2-n-octyl-4-bromo-5-chloro-3-isothiazolone, and the yield is 35 to 43%. The provided preparation method overcomes the shortages of conventional synthesis technology. A novel synthesis method of 2-n-octyl-4-bromo-5-chloro-3-isothiazolone is provided.

STABLE COMPOSITIONS OF THIABENDAZOLE AND IODINE-CONTAINING FUNGICIDES

The present invention relates to stable compositions for the fungicidal equipment of thermoplastic polymers, in particular PVC, comprising thiabendazole, at least one iodine-containing fungicide and at least one epoxide and optionally further fungicidally active compounds, and also to methods for preparing these formulations and to uses thereof for the protection of thermoplastic polymers against attack and destruction by microorganisms. Moreover, the invention relates to mold-resistant PVC materials equipped with the compositions according to the invention.

Preparation of N-Substituted Isothiazolinone Derivatives

Provided is a process for the preparation of an N-substituted isothiazolinone derivative having the general formula (I), comprising reacting N-substituted 3-mercaptopropionamides of formula (II) or N,N′-bis-substituted 3,3′-dithiodipropionamides of formula (III) with sulfuryl chloride in the absence of solvents. Also provided is a process for the preparation of a compound having the general formula (III), comprising reacting a methyl ester of formula (IV) with an amine of formula (V) in a solvent of methanol. As no addition solvent is used in the process of the invention, the cost of manufacturing and pollution to the environment can be reduced.

Use of riboflavin and flavin derivatives as chitinase inhibitors

The invention relates to the use of riboflavin and of flavin derivatives with chitinase-inhibitory action for controlling arthropods, nematodes and chitin-containing fungi.

Bromonitrothienyldioxanes

The invention relates to novel 5-bromo-5-nitro-2-thienyl-1,3-dioxanes of the formula (I) in which R1, R2 and R3 are as defined in the description are highly suitable for use as biocides for protecting plants and industrial materials.

3-NITROISOXAZOLES AND THEIR USE IN THE PROTECTION OF MATERIALS

The 3-nitroisoxazoles of the formula (I) in which R1 and R2 are each as defined in the description, some of which are known, are highly suitable for use as biocides for protecting industrial materials.