4,5-Dichloro-2-n-octyl-4-isothiazolin-3-one

solid

Preparation of N-n-octyl isothiazolinones (including N-n-octyl-4-isothiazolin-3-one (OIT) and N-n-octyl-4, 5-dichloro-4-isothiazolin-3-one (DCOIT))The reaction scheme is as follows: 200 ml (330 g, 2.44 mol) of sulfuryl chloride was added into a 1, 000 ml reaction flask, to which 648 g (1.5 mol) of N, N'-di-n-octyl-3, 3'-dithiodipropionamide was then added for 6.5 hours (about 100 g per hour) under agitation. After 3 hours of reaction, chlorine was aerated into the reaction mixture at about 50 g per hour for 13 hours (about 650 g in total, 9.15 mol). When the temperature of the reaction mixture reached 40° C., the mixture was cooled with saline and maintained at a temperature of 40-45° C. After the aeration of chlorine was completed, the reaction mixture was stirred at the same temperature for 2 hours.The reaction mixture was washed with hot water at 50° C. in another 1, 000 ml reaction flask till it became weakly acidic, and, if desired, sodium bicarbonate was used to neutralize excessive acid. The precipitate was recrystallized in methanol to give 190 g of DCOIT (purity >95percent). The recrystallization mother liquor was then extracted successively with petroleum ether and methanol to afford 61 g of OIT (purity >93percent, yield 19percent) and 49 g of DCOIT (purity >95percent). The total yield of DCOIT is 56.5percent.Equipped with a thermometer, a stirrer, and a reflux condenser.And a 2L four-port reaction bottle with a constant pressure funnel.Add 648 g (1.5 mol) of N, N-di-n-octyl-3, 3 dithiodipropionamide, 1.5L of dichloromethane will contain 32.4g of titanium tetrachloride, 32.4g2-methoxythiophene, 12.9gA mixed catalyst of 18-crown-6 is added to the reaction system.The temperature of the control system was at -5 C, and 1065 g (15 mol) of chlorine gas was slowly introduced at a constant rate.The access time is controlled for 3 hours and then warmed to 40 C.After the reaction, 400 g of water was added to decompose unreacted sulfonyl chloride.Stir for 20 minutes, let stand, dispense, The lower organic phase is adjusted to a neutral pH with a saturated aqueous solution of sodium bicarbonate.The solvent is separated, separated, dried, and distilled, and then recrystallized from petroleum ether.Obtaining 4, 5-dichloro-N-n-octylisothiazolinone as a white solid powderThe yield was 74.7% and the purity was 99.1%.67 g (1 mol) of pyrrol was reflux-boiled with 92 g (1 mol) of 4-methylbenzaldehyde in 400 ml of methanol+20 ml conc. HCl in a nitrogen atmosphere for 1 hour, whereby a dark blue solution of tetratolyl porphyrine was spontaneously obtained. After adding 136 g (1 mol) of zinc chloride, a suspension of the porphyrine zinc complex was obtained. 282 g of 4, 5-dichloro-2-octylisothiazolone (DCOIT) was then added and after a 1 hour agitating phase, the deep-blue coordination compound formed was extracted. After drying, 310 g of tetratolyl porphyrine/Zn/DCOIT coordination compound was obtained.With a mechanical stirring, reflux condensation pipe and of the exhaust gas the alkali absorption device 250 ml four port in the reactor, to add a new preparation of 3-mercapto-N-amide octyl third 25g (0.11mol, 96%, 1eq), 1, 2-dichloroethane 100g, the start-up of heating under nitrogen protection 35-40C, sulfuryl chloride dropwise under stirring 54g (0.4mol, 99%, 3.6eq), after-reaction add 0.5-1h, then began instillment bromide 32g (0.2mol, 99%, 2.5eq), is in the process of dropping the color change of the system, add insulation reaction after 2.5-3h, sampling analysis, the product 2- octyl -4-bromo-5-chloro-3-isothiazolone GC content is 55%, the major impurity is the system 2- octyl -4, 5-dichloro-3-isothiazolone.Preparation of N-n-octyl isothiazolinones (including N-n-octyl-4-isothiazolin-3-one (OIT) and N-n-octyl-4, 5-dichloro-4-isothiazolin-3-one (DCOIT))The reaction scheme is as follows: 200 ml (330 g, 2.44 mol) of sulfuryl chloride was added into a 1, 000 ml reaction flask, to which 648 g (1.5 mol) of N, N'-di-n-octyl-3, 3'-dithiodipropionamide was then added for 6.5 hours (about 100 g per hour) under agitation. After 3 hours of reaction, chlorine was aerated into the reaction mixture at about 50 g per hour for 13 hours (about 650 g in total, 9.15 mol). When the temperature of the reaction mixture reached 40 C., the mixture was cooled with saline and maintained at a temperature of 40-45 C. After the aeration of chlorine was completed, the reaction mixture was stirred at the same temperature for 2 hours.The reaction mixture was washed with hot water at 50 C. in another 1, 000 ml reaction flask till it became weakly acidic, and, if desired, sodium bicarbonate was used to neutralize excessive acid. The precipitate was recrystallized in methanol to give 190 g of DCOIT (purity >95%). The recrystallization mother liquor was then extracted successively with petroleum ether and methanol to afford 61 g of OIT (purity >93%, yield 19%) and 49 g of DCOIT (purity >95%). The total yield of DCOIT is 56.5%.EXAMPLE 5 Reaction of N-Octylacrylamide with SM N-Octyl acrylamide (8.4 g; 0.046 moles) was mixed with triethylamine (26 g; 0.026 moles) and 18 ml. of chlorobenzene. To the mixture was added dropwise SM (0.156 moles); exotherming to about 100 C. was observed. The reactants were held for 19 hours at 125 C. A yield of 22% of 4, 5-dichloro-2-N-octylisothiazolone was obtained.Preparation of Compound 5: [4-chloro-2-n-octyl-3-isothiazolon-5-yl]-(1-oxypyridin-2-yl)sulfide (see Scheme B): To a well stirred solution of 1.2 g (0.004 mol) of 4, 5-dichloro-2-n-octyl-3-isothiazolone (compound 4) in 8.8 g of ethanol was added 1.1 g (0.003 mol) of a 40% aqueous solution of 2-mercaptopyridine-N-oxide, sodium salt (compound 2). The pH of the solution was adjusted to 8.5 by using a 0.5% sodium hydroxide solution (aqueous). The reaction mixture was stirred for an additional 4 hours and then the ethanol was removed under reduced pressure. The sticky solid obtained was dissolved in methylene chloride and washed repeatedly with water. The methylene chloride was dried over anhydrous magnesium sulfate and the methylene chloride removed under reduced pressure to give 0.9 g (82%) of compound 5 as a yellow oil: 1H NMR (CDCl3, 300 MHz), delta 0.80 (m, 3H), 1.23 (m, 10H), 1.70 (m, 2H), 3.80 (m, 2H), 7.01 (m, 1H), 7.22 (m, 2H), 8.25 (m, 1H); 13C NMR (CDCl3), 67 13.1, 21.6, 25.5, 25.9, 28.0, 28.4, 30.7, 44.6, 122.1, 122.5, 122.8, 125.8, 135.5, 137.8, 145.4, 161.4. Elemental analysis: calculated for C16H21ClN2O2S2: C, 51.5; H, 5.7; N, 7.5; found: C, 51.4, H, 5.8, N, 7.3.or conventional antifouling active compounds such as 4, 5-dichloro-2-octyl-4-isothiazolin-3-one, diiodo-methylparatryl sulfone, pyridine-triphenylborane, tetrabutyldistannoxane, 2, 3, 5, 6-tetrachloro-4-(methylsulfonyl)pyridine, 2, 4, 5, 6-tetrachloroisophthalonitrile, tetramethylthiuram disulfide and 2, 4, 6-trichlorophenylmaleimide.Morpholine Derivatives, Such as: aldimorph, dimethomorph, dodemorph, falimorph, fenpropidin, enpropimorph, tridemorph, trimorphamide and their arylsulfonates, such as p-toluenesulfonic acid and p-dodecylphenyl-sulfonic acid; Benzothiazoles, Such as: ... N-(2-hydroxypropyl)-amine-methanol; N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, 4, 5-dichloro-N-octylisothiazolin-3-one, 5-chloro-N-octylisothiazolinone, N-octylisothiazolin-3-one, cinnamaldehyde, ...Benzimidazole Compounds such as ... 2-(41-thiazolyl) benzimidazole (Thiabendazole) Methyl (1-butylcarbamoyl)-2-benzimidazole carbamate (Benomyl) N-Methylisothiazolin-3-one 5-Chloro-N-methylisothiazolin-3-one 4, 5-Dichloro-N-octylisothiazolin-3-one N-Octylisothiazolin-3-one Tetrachloro-4-methyl sulphonyl pyridine Tris-(N-cyclohexyldiaziniumdioxy) aluminium ...... alcohol mono-(poly)-hemiformal, oxazolidines, hexa-hydro-S-triazines, N-methylolchloroacetamide, paraformadehyde, nitropyrin, oxolinic acid, tecloftalam; tris-N-(cyclohexyldiazeniumdioxy)-aluminium, N-(cyclo-hexyldiazeniumdioxy)tributyltin or K salts, bis-N-(cyclohexyldiazeniumdioxy)-copper; N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, 4, 5-dichloro-N-octyl-isothiazolin-3-one, N-octyl-isothiazolin-3-one, N-methylolchloroacetamide;Morpholine derivatives, such as: aldimorph, dimethomorph, dodemorph, falimorph, fenpropidin fenpropimorph, tridemorph, trimorphamid and their arylsulphonates, such as, for example, p-toluenesulphonic acid and p-dodecylphenyl-sulphonic acid; Benzothiazoles, such as: ... N-(2-hydroxypropyl)-aminemethanol; N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, 4, 5-dichloro-N-octylisothiazolin-3-one, 5-chloro-N-octylisothiazolinone, N-octylisothiazolin-3-one, cinnamaldehyde, ......ohol mono- (poly)-hemiformal, oxazolidines, hexa-hydro-S-triazines, N-methylolchloroacetamide, paraformadehyde, nitropyrine, oxolinic acid, tecloftalam; tris-N-(cyclohexyldiazeniumdioxy)-aluminium, N-(cyclo-hexyldiazeniumdioxy)-tributyltin and K salts, bis-N-(cyclohexyldiazeniumdioxy)-copper. N-Methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, 4, 5-dichloro-N-octyl-isothiazolin-3-one, N-octyl-isothiazolin-3-one, N-methylolchloroacetamide;...zyl alcohol mono(poly)hemiformal, oxazolidines, hexa-hydro-S-triazines, N-methylol chloracetamide, paraformadehyde, nitropyrin, oxolinic acid, tecloftalam; tris-N-(cyclhexyldiazeniumdioxy)-aluminium, N-(cyclo-hexyldiazeniumdioxy)-tributyl-tin or K salts, bis-N-cyclohexyldiazeniumdioxy)-copper; N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-on, 4, 5-dichloro-N-octyl-isothiazolin-3-one, N-octyl-isothiazolin-3-one, N-methylol chloracetamide;...l alcohol mono-(poly)-hemiformal, oxazolidine, hexa-hydro-S-triazine, N-methylolchloroacetamide, paraformaldehyde, nitropyrin, oxolic acid, tecloftalam; tris-N-(cyclohexyldiazeniumdioxy)-aluminium, N-(cyclo-hexyldiazeniumdioxy)-tributyltin and K salts, bis-N-(cyclohexyldiazeniumdioxy)-copper; N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, 4, 5-dichloro-N-octylisothiazolin-3-one, N-octyl-isothiazolin-3-one, 4, 5-trimethyleneisothiazolinone, 4, 5-benzisothiazolinone and N-methylolchloroacetamide;Quaternary ammonium compounds such as, for example, ... 2-(4'-thiazolyl)benzimidazole (common name: thiabendazole) and methyl (1-butylcarbamoyl)-2-benzimidazolecarbamate (common name: benomyl). N-methylisothiazolin-3-one. 5-chloro-N-methylisothiazolin-3-one, 4, 5-dichloro-N-octylisothiazolin-3-one and N-octylisothiazolin-3-one....lcohol mono-(poly)-hemiformal, oxazolidines, hexa-hydro-S-triazines, N-methylolchloroacetamide, paraformadehyde, nitropyrin, oxolinic acid, tecloftalam; tris-N-(cyclohexyldiazeniumdioxy)-aluminium, N-(cyclo-hexyldiazeniumdioxy)-tributyltin and K salts, bis-N-(cyclohexyldiazeniumdioxy)-copper; N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, 4, 5-dichloro-N-octylisothiazolin-3-one, N-octyl-isothiazolin-3-one, N-methylolchloroacetamide;To 13.28 g. of Celite545 in each of three glass bottles was added 1 g. of the following isothiazolones in 20 ml. of methanol: (a) 2-octyl-3-isothiazolone; (b) 4, 5-dichloro-2-cyclohexyl-3-isothiazolone; and (c) 4, 5-dichloro-2-octyl-3-isothiazolone.Benzimidazole Compounds such as ... N-Methylisothiazolin-3-one 5-Chloro-N-methylisothiazoline-3-one 4, 5-Dichloro-N-octylisothiazolin-3-one... alcohol mono(poly)-hemiformal, oxazolidine, hexa-hydro-S-triazines, N-methylolchloroacetamide, paraformadehyde, nitropyrin, oxolinic acid, tecloftalam; Tris-N-(cyclohexyldiazeneiumdioxy)-aluminium, N-(cyclohexyldiazeneiumdioxy)-tributyltin or K salts, bis-N-(cyclohexyldiazeniumdioxy)-copper; N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, 4, 5-dichloro-N-octylisothiazolin-3-one, N-octyl-isothiazolin-3-one, 4, 5-trimethylene-isothiazolinone, 4, 5-benzoisothiazolinone, N-methylolchloroacetamide;morpholine derivatives such as: aldimorph, dimethomorph, dodemorph, falimorph, fenpropidin fenpropimorph, tridemorph, trimorphamid and their arylsulphonate salts such as, for example, p-toluenesulphonic acid and p-dodecylphenyl-sulphonic acid; benzothiazoles such as: ... N-(2-hydroxypropyl)-amine-methanol; N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, 4, 5-dichloro-N-octylisothiazolin-3-one, 5-chloro-N-octylisothiazolinone, N-octyl-isothiazolin-3-one, 4, 5-trimethylene-isothiazolinone, ...morpholine derivatives such as: aldimorph, dimethomorph, dodemorph, falimorph, fenpropidin fenpropimorph, tridemorph, trimorphamid and their arylsulfonate salts such as, for example, p-toluenesulfonic acid and p-dodecylphenylsulfonic acid; benzothiazoles such as: ... hexa-hydro-S-triazine, N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, 4, 5-dichloro-N-octylisothiazolin-3-one, 5-chloro-N-octylisothiazolinone, N-octyl-isothiazolin-3-one, 4, 5-trimethylene-isothiazolinone, ...morpholine derivatives such as: aldimorph, dimethomorph, dodemorph, falimorph, fenpropidin, fenpropimorph, tridemorph, trimorphamid and their arylsulphonates such as, for example, p-toluenesulfonic acid and p-dodecylphenyl-sulphonic acid; benzothiazoles such as: ... N-(2-hydroxypropyl)-amine-methanol; N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, 4, 5-dichloro-N-octylisothiazolin-3-one, 5-chloro-N-octylisothiazolinone, N-octyl-isothiazolin-3-one, 4, 5-trimethylene-isothiazolinone, ...morpholine derivatives such as:aidimorph, dimethomorph, dodemorph, falimorph, fenpropidin, fenpropimorph, tridemorph, trimorphamid and their arylsulfonate salts such as, for example, p-toluenesulfonic acid and p-dodecylphenylsulfonic acid;benzothiazoles such as:2-mercaptobenzothiazole;2, 6-dichloro-N-(4-trifluoromethylbenzyl)benzamide, tecloftalam;N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, 4, 5-dichloro-N-octylisothiazolin-3-one, 5-chloro-N-octylisothiazolinone, N-octylisothiazolin-3-one, 4, 5-trimethyleneisothiazolinone, 4, 5-benzisothiazolinone;

It is a low-toxicity, high-efficiency, wide-ranging fungicide, mainly used to control mold. It can also be used in adhesives, polymeric emulsions, decorative wood surfaces, sealants and paints to prevent the growth of fungi and bacteria

Molecular Weight:282.2
XLogP3:5.1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:7
Exact Mass:281.0407907
Monoisotopic Mass:281.0407907
Topological Polar Surface Area:45.6
Heavy Atom Count:16
Complexity:281
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes