 Method of obtaining derivatives of benzoxazine-2-on
专利摘要:
METHOD OF OBTAINING ARBITRARY BENZOXAZIN 2-ONA of the general formula 1 where R is a hydrogen atom, acetyl, benzoyl, p-toluenesulfonyl or methanesulfonyl, D is an unbranched or branched alkylene group with 2-6-carbon atoms; an alkyl group with 1-3 carbon atoms, unsubstituted or substituted by a phenyl group, or a phenyl group, and these phenyl groups may be substituted by an alkyl group with 1-4 carbon atoms, a halogen atom, an alkoxy group with 1-3 carbon atoms, a hydroxy group, cyclohexyl or phenyl group; an alkyl group with 4-8 carbon atoms, a cycloalkyl group with 3-7 carbon atoms, a phenyl group disubstituted with an alkyl group with 1-4 carbon atoms, an alkoxy group with 1-carbon carbon and / or halogen atoms oxyphenyl or an aminophenyl group, a mono- or disubstituted alkyl group with 1–4 carbon atoms, an alkoxy group with 1–3 carbon atoms and / or halogen atoms, the substituents of the phenyl core may be the same or different, pyridsh1-C-hydroxy, pyridine; or a pyrimidine group, unsubstituted or substituted by one or two alkyl groups with 1–3 carbon atoms / m3 of carbon, triazolyl, unsubstituted or substituted by one or two alkyl groups with 1–3 carbon atoms, or 2-benzthiazolyl; RO- may be the same or different — a hydrogen agom, a phenyl group, an alkyl group with 1-6 carbon atoms or a cycloalkyl group with 3-7 carbon atoms; a hydrogen atom or an alkyl group with 1 to 3 carbon atoms. 公开号:SU1138025A3 申请号:SU833583668 申请日:1983-04-26 公开日:1985-01-30 发明作者:Нарр Бертхольд；Никль Иозеф；Мюллер Эрих；РОХ Йозеф；Гаарманн Вальтер；Вейзенбергер Иоганнес-Максимилиан 申请人:Др.Карл Томэ Гмбх (Фирма)； IPC主号:
专利说明:
R. is a hydrogen or halogen atom, a nitro or alkyl group with 1-3 carbon atoms (R, is a hydrogen or halogen atom or an alkyl group with 1-3 carbon atoms, characterized in that the hydroxy compound of the general formula 11 where R, R, Rj, Rg have the indicated meanings, are reacted with a compound of formula 111 Z-D-ftR, where A, D and R have the indicated values I Z is a nucleophilic substitutable group such as a halogen atom, p-toluenesulfonyloxy or methanesulfonyloxy group, in the solvent medium, in the presence of an alkaline base or alcoholate at a temperature from room temperature to the boiling point of the solvent. The invention relates to a method for producing new biologically active chemical compounds, specifically to a method for producing benzoxazin-2-one derivatives of the formula RI-ADO where A is the radical -S-, -SOj, -RNS- or RN-SO-, where R- atoM hydrogen, acetyl benzoyl, p-toluenesulfonyl or methanesulfonyl P is a linear or branched alkylene group with 2-6 carbon atoms) R is an alkyl group with 1-3 carbon atoms, an unsubstituted or substituted phenyl group, or a phenyl group, and these phenyl groups can be substituted by an alkyl group with 1-4 atoms at halogen, alkoxy group with 1-3 carbon atoms, hydroxy group, cyclohexyl or phenyl group, alkyl group with 4-8 carbon atoms, cycloalkyl group with 3-7 carbon atoms, phenyl group, disubstituted with alkyl group with 1-4 atoms carbon, alkoxy group with 1-3 carbon atoms and / or halogen atoms, hydroxyphenyl or aminophenyl group, mono- or disubstituted by an alkyl group with 1-4 carbon atoms, alkoxy group with 1-3 carbon atoms and / or halogen atoms, with the substituents of phenyl core can be the same or different, pyridyl-N-hydroxy, pyridine or pyrimidine ring, unsubstituted or. substituted with one or two alkyl groups with 1-3 carbon atoms, triazolyl, unsubstituted or substituted with one or two alkyl groups with 1-3 carbon atoms, or 2-benzthiazolyl, can be the same or different - a hydrogen atom, a phenyl group, an alkyl group with 1-6 carbon atoms or a cycloalkyl group with 3-7 carbon atoms; R-- a hydrogen atom or an alkyl group with 1 to 3 carbon atoms, Rp a hydrogen or halogen atom, a nitro or alkyl group with 1 to 3 carbon atoms, a hydrogen or halogen atom or an alkyl group with 1 to 3 carbon atoms that can find application in medicine. The compounds of formula 1 exhibit an antithrombotic effect. A known method for producing carbostyryl or oxindole derivatives of the formula R9 W. 0-i) i- $ On, R8 IV where W is a vinylene group, a methylene or ethylene group is -0.1 or ZI has the same meanings as D in the compound of the formula 1 Ig, R, HR, o have the same meanings as R, R, R and R in the compound of the formula t, which consists in the fact that the oxo compound of the formula V, where R, Rg and have the indicated meanings, is reacted with the compound Z, -D, where D, Rg and ha have the indicated values i Z, is a halogen atom and an ester radical. sulfonic acid, at 20-250 ° C in the presence of an alkaline base. The compounds of formula IV have an antithrombotic effect However, these compounds inhibit platelet phosphodiesterase at sufficiently high concentrations. The purpose of the invention is to obtain new benzoxazin-2-one derivatives with improved antithrombotic effect. The goal is achieved based on the known reaction of the preparation of ethers by the interaction of oxo compounds with halogen-containing compounds or esters of p-toluenesulfonic acid, a method for the preparation of benzoxazin-2-one derivatives of the formula I, which consists in the fact that the oxo compound of the formula where R2, R, R. 5 have the indicated values , is reacted with a compound of the formula; ZDAR, where A, D and R have the indicated meanings, Z is a nucleophilic substitutable group, such as a halogen atom, p-toluenesulfonyloxy or methanesulfonyloxy group, in a solvent environment, in the presence of an alkaline base or an alcoholate, at a temperature from room temperature to the boiling point of the solvent. The reaction is advantageously carried out in solvents or solvent mixtures such as methanol, ethanol, dioxane, tetrahydrofuran, chloroform or toluene, preferably in an anhydrous aprotic solvent such as acetone, dimethylformamide or dimethyl sulfoxide, in the presence of sodium carbonate, potassium carbonate sodium hydroxide or sodium ethylate, ethylate sodium. If a compound of general formula 1 is prepared, in which RX is a hydrogen atom, it can be converted by alkylation to the corresponding compound of general formula 1, in which R represents an alkyl group with 1 to 3 carbon atoms. Additional alkilirovanye usual but carried out with an alkyl halide such as methyl iodide or propyl bromide or ester of a sulfonic acid, such as dimethyl sulfate, preferably in the presence of a base such as sodium hydroxide or pyridine, optionally in the presence of reaction accelerators, such gidroTensulfata tetrabutylammonium, and pre respectfully in a solvent, e.g. methanol, ethanol, water, caustic soda, tetrahydrofuran or disxane, at 0-80 ° C, preferably at room temperature. The compounds of general formula tl and III used as starting materials are partially known, they are prepared by conventional methods (see examples A to G). Thus, a hydroxyl compound of general formula 11 is obtained by reacting the corresponding carbonyl compound with the corresponding Grignard compound, followed by with phosgene and radical cleavage used for the hydroxyl group as a protecting radical. A compound of the general formula ttl is obtained by reacting the corresponding 0.00-disubstituted alkane with the corresponding mercapto compound, if necessary with a subsequent oxidation. In addition, the starting compound of the general formula II thus obtained can then be converted to the corresponding halogen compound by chlorination or bromination, for example, by chlorine, sulfuryl chloride or bromine, or to the corresponding nitro compound by means of nitric acid. 1 Getting the original products. jnrimer ... 6-Methoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one. A. 2-Amino-5-methoxy phenyldimethyl carbinol. While stirring, 102 g (4.2 mol) of magnesium shavings in 300 ml of absolute ether and a solution of 261 ml (4.2 mol) of methyl iodide in 1000 ml of absolute sulfur ether are added dropwise to the suspension for 2.5 h and stirred further at 256 for half an hour. Then, drops are added under the conditions that the temperature does not exceed 20-25 ° C, a solution of 181.2 g (1 mol) of 5-methoxyanthranilic acid methyl ester in 1.5 liters of absolute ether within half an hour. After further stirring for 1 h, it is poured onto ice-chloride containing ammonium chloride, the ether phase is separated, washed with ammonium chloride water, dried with sodium sulfate and distilled off the ether. B. 6-Methoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one. The residue of 2-amino-5-methoxyphenyl dimethyl carbinol, which remains after the distillation of ether, is dissolved without further purification in 1.5 liters of chloroform, mixed with 276.4 g (2 mol) of potassium carbonate and heated to 40 C. To this solution is added 600 ml. ml of a 20% phosgene solution in toluene (1.2 mol) for 2 hours at a rate such that the temperature of the reaction mixture does not exceed 40-50 ° C, and foaming may occur. After the addition, it is left overnight at room temperature. Then 1 liter of water is mixed, the chloroform and toluene phases are separated and the aqueous phase is extracted several times with chloroform, to which a small amount of methanol is added. The combined organic extracts are washed with water, dried with sodium sulfate and the solvents are distilled off. The crystalline residue is recrystallized from toluene and ethyl acetate 9: 1. M.p. 182-1 W C, yield 130 g (65% of theory, in terms of the used methyl ester of 5-methoxy-anthranilic acid). The following compounds are prepared analogously. 6-Methoxy-4,4-di-n-hexyl-4H-3, 1-benzoxazin-2-one from 5-methoxyanthranilic acid methyl ester, bromide n-hexyl magnesium and phosgene. M.p. YuT-YuZ S, output of 70.8% of theory. 6-Methoxy-4,4-diphenyl-4H-3,1-benzoxazin-2-one from methyl ester of 5-methoxyanthranilic acid, phenylmagnesium bromide and phosgene. M.p. 237 C, the output of 69.5% of theory. 6-Methoxy-4,4-dicyclohexyl-4H-3, 1-benzoxazin-2-one from methyl ester of 5-methoxyanthranilic acid, cyclohexyl magnesium and phosgene. M.p. 269-271 C, yield of 50.4% of theory. 6-methoxy-4-isopropyl-4H-3,1gbenzoxazin-2-one from 5-methoxy-2-aminobenzaldehyde (obtained from 5-methoxy-2-nitrobenzaldehyde and Pt / li-y at a pressure of 30 bar and 35 ° C) , isopropylmagnesium iodide and phosgene. M.p. 124-125 ° C, the yield of 37.1% of theory. 6-Methoxy-4-ethyl-4H-3,1-benzoxazIN-2-OH from 5-methoxy-2-aminobenzaldehyde, ethylmagnesium bromide and phosgene. M.p. 88-89 ° С, yield 30.2% of the procedure. 6-Methoxy-4-phenyl-4H-3,1-benzoxazIN-2-OH from 5-methoxy-2-aminobenzal dehydro, phenylmagnesium bromide and phosgene. So pl.- 157-158 ° C, the output of 36.32 theory. 6-Methoxy-4,4-diethyl-4H-3,1-benzoxazin-2 from methyl ester of 5-methoxyanthranilic acid, ethylmagnesium bromide and phosgene. So pl.123125 ° C, the yield of 90.1% of theory. 6-Methoxy-4-methyl-4H-3,1 -6eH3j-oxazin-2-one from 5-methoxy-2-aminobenzaldehyde, methylmagnesium iodide and phosgene. M.p. 120-121 ° C, yield of 20.2% of theory. 5-Methoxy-4,4-dimesht-4H-3,1-benzoxazin-2-one from methyl ester 6-methoxy-anthranilic acid methylmagnesium and phosgene. M.p. 139-141C, yield 22% of theory. 7-Methoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one from methyl 4-methoxyanthranilic acid, methylmagnesium iodide and phosgene. M.p. 119-121 ° C, yield 62% of theory. 8-Methoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one from methyl 3-methoxyanthranilic acid, methylmagnesium iodide and phosgene. M.p. 95-96 0, yield 42.1% of theory. 6-Methoxy-4,4,7-trimethyl-4H-3,1-benzoxazin-2-one from methyl ester of 5-methoxy-4-methyl anthranilic acid, methylmagnesium iodide and phosgene. M.p. 134-135 ° C, 45.5% of theory. 6. Methoxy-4,4-8-trimethyl-4H-3, 1-benzoxazin-2-one from methyl ester of 5-methoxy-Z-methylanthrnilic acid, magnesium ipide of ifosgene. M.p. 218-219 ° C, water about 5.8% of theory. 6-Methoxy-5,7-dichloro-4,4-dimeti $ 1-4H-3, 1-benzoxazin-2-one from methyl ester 5-methoxy-4,6-di. . chloroanthranilic acid, methylmagnesium iodide and phosgene. Mp 203-204 yield 44.0% of theory. , 6-Methoxy-5,7-dimethyl-4H-3,1-benzoxazin-2-one from complex methyl 5-methoxy-4, b-dimethyl anthranilic acid, methyl magnesium iodide and phosgene. M.p. 152-153 ° C, yield 38.7%; theories. PRI me R B. 6-Methoxy-4H-3,1-benzoxazin-2-one. A. 2-Amino-5-methoxy-benzyl alcohol. 181.2 g (1 mol) of 5-methoxy-2-nitr benzaldehyde (obtained by methylation of 2-nitro-5-hydroxybenzaldeG1 with methyl iodide and potassium t-butylate in dimethyl sulfoxide) is dissolved in 1.8 l of methanol, mixed, 5 g Rene nickel and subjected to hydrogenation at room temperature and pressure of 5 bar. After 10 hours the absorption of hydrogen is complete. Suction is carried out from the catalyst and methanol is distilled off. B. 6-Methoxy-4H-3,1-benzoxazin-2-one. The residue after distillation of methanol, without further purification, is dissolved in 1 liter of chloroform and mixed with 175 g (1.25 mol) of potassium carbonate. With stirring, 553 ml (1.05 mol) of a 20% phosgene solution in toluene at 50 ° C are added dropwise to this suspension. After 2 hours of additional stirring at room temperature, the mixture is poured onto ice-cold water, the chloroform and toluene phases are separated and the aqueous phase is extracted several times with chloroform and 5/1 methanol. The combined organic extracts are washed with water, dried sodium sulfate and the solvents are distilled off. The residue is purified by chromatography on a column (silica gel, chloroform / acetone 19: 1). The remaining after the solvent has been distilled off, the crystals have an mp. 154-156 ° C. The output of 110.5 g (61.7% of theory). The following compounds are prepared in a similar manner: 6-Methoxy-7-chloro-4H-3, 1-benzox in-2-one, mp 208-210 °, 38.7% of theory. Example B B. 6-Oxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, 2.37.5 g (1.146 mol) 6-methoxy-4, 4-dimethyl-4H- 3,1-benzoxazin-2 is dissolved in 2.4 l of dry ethylene chloride and, with stirring, is mixed with 125 ml (330.3 g 1.3 of boribtrimide at minus 30 / nus). After the addition, it is heated to room temperature and left overnight. Then it is added dropwise with cooling and stirred with 50% ethanol, the mixture is concentrated to 500 ml and diluted with 3 l of water. The precipitated precipitate is sucked off and dried, mp 202-204 ° C (from a complex ether and petroleum ether), yield 223.3 g (99.8% of theory). the following compounds are prepared in person: 6-OXII-4H-3,1-benzoxazin-2-one with mp 244-245 s and 78.5% yield of theory, 6-hydroxy-4,4-di-n-hexyl -4H-3,1-benzoxazin-2-one with mp 144-146 and a yield of 92.4% of theory. 6-Oxy-4,4-diphenyl-4H-3,1-benzoxazin-2-one with mp 239 ° C (decomposition) and 90.0% yield of theory. 6-Oxy-4-isopropyl-4H-3,1-benz oxazin-2-one with mp 215-216 ° C and yield 77 , 6% of theory. 6-OXI-4-ETHIL-4N-3,1-bn-oxazi-2-one with m.p. 216-218 ° C and the yield of 68.5% of theory. 6-Oxy-4,4-dicyclohexyl-4H-3, 1-benzoxazin-2-one with so pl. 280 and the yield of 97.8% of theory .. 6-Oxy-4,4-diethyl-4H-3,1-benzoxazin-2-one with so pl. 194-195 C and the course of 95.5% of theory. 6-Oxy-4-methyl-4H-3,1-benzoxazIN-2-OH with so pl. (decomposition; Yield: 75.8% of theory. 7-Oxy-4,4-dimethyl-4H-3,1-benz oxazin-2-one with mp 180-182 C and yield 96.8% of theory. 5- Hydroxy-4,4-dimethyl-4H-3,1-benz oxazin-2-one with a melting point of 251 C and a yield of 79% of the theory. 8-Hydroxy-4,4-dimethyl-4H-3,1- benz ZIN-2-OH with mp 203-205 s and output 90% of theory. 6-Oxy-4,4,8-trimethyl-4H-3,1-benzoxazin-2-one with t, pl. 174 With (decomposition) and a yield of 94.3% of the theory of b-Oxy-4, 4, 7-trimethyl-4E -3, 1-benzoxazi {-2-one with mp 150-152 C and a yield of 85.8% of the theory. 8-Chloro-6-hydroxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one with a melting point of 196-198 C and a yield of 52% of the theory. 7-Chloro-6-hydroxy- 4,4-dimethyl-4I-3,1-benzoxazin-2-one with a melting point of 218-219 C and a yield of 97.1% of theory. 7-Bromo -6-hydroxy-4,4-dimesh-1-4H-3, 1-benzoxazin-2-one with a melting point of 157158 С and a yield of 96% of theory. 8-Bromo-6-hydroxy-4,4-dimethyl-4H -3, 1-benzoxazin-2-one with mp 212-214 C and a yield of 46.7% of theory. 7.8-Dibrom-6-hydroxy-4,4-dimethyl-4H-3, 1-benzoxazine -2-one with mp 194195 C and a yield of 24% of theory. 6-Oxy-7-chloro-4H-3,1-benzoxazing -2-one with mp 250 C (decomposition) and yield 96, 2% of theory. b-Oxy-5,7-dichloro-4,4-dimethyl-4H-3, 1-benzoxazin-2-one with so pl.215217 C and a yield of 88.0% of theory. b-Oxy-5,7-dimethyl-4H-3,1-benzoxazin-2-one with a mp of 210–10 lc and a yield of 70.5% of theory. PRI me R G. 8-Chloro-6-methoxy-4, 4-dimesht-4N-3,1-benzoxazin-2-one and 7-chloro-6-methoxy-4,4-dimethyl-4H- 3, 1-benzoxazin-2-one. P. solution 79 g (0.38 mol) of 6-methoxy-4, 4-dimethyl-4H-3,1-benzoxazin-2-one in 1000 ml of chloroform is mixed with 56.68 g (0.42 mol) of sulfuryl chloride and stirred for 6 hours at 10-20 ° C. After overnight, the reaction mixture was mixed with an aqueous solution of sodium carbonate, the organic phase was separated, washed with water, dried with sodium sulfate, and chloroform was distilled off. The residue is separated into isomers by chromatography on a column (silica gel, ethylene chloride / acetone 19: 1). The 1 / rations are concentrated to dryness and the residue is recrystallized from acetic ester and diisopropyl ether. 1) 8-Chloro-6-methoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one with mp 1656157 C and 47.3 g yield (51.6 theory). 2) 7-Chloro-6-met.oxn-4,4-dimethyl-4H-3, 1-benzoxazin-2-one with m.p. 165-167 C and a yield of 18.9 g (20.6% of eoria). PRI me R D. 8-Bron-6-methoxy4, 4-dimvtil-4H-3,1-benzoxazin-2-one 7-bromo-6-methoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one. 82.7 g (0.4 mol) of 6-methoxy-4,4 dimethyl-4H-3, 1-benzoxazin-2-one. It is dissolved in 800 ml of dioxane and 5 m is mixed with 67.1 g (21.5 ml of 0.42 mol) of bromine at room temperature. After 3 hours of stirring, 67.1 g of bromine was added, and after another 3 hours, 67.1 g of bromine was added again. Continue to move overnight. The reaction mixture is then mixed with ice water and sodium bisulfite solution and extracted with ethyl acetate. The extract is washed with water, dried with sodium sulfate and distilled ethyl acetate. The residue was separated into isomers by chromatography on a column (silica gel, ethyl 1 | chloride / acetone 60: 1). The pure fractions are concentrated and recrystallized with ethyl acetate and isopropyl ether. 1) 8-Bromo-6-methoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one with mp 128130 C (there is still a small amount of 7,8-dibromo-6-methoxy- 4,4-dimethyl-4H-3, 1-benzoxazin-2-one) in 45 g (39.3% of theory). thirty 2) 7-Bromo-6-methoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one with a mp of 174175 ° C and a yield of 33.7 g (29.5% of theory). PRI me R E. 6-Acetoxy-8- 35 CHLOR-4H-3,1-benzoxazin-2-one. 14.5 g (0.07 mol) of 6-acetoxy-4H3, 1-benzoxazin-2-one (obtained from 6-OXI-4H-3,1-benzoxazin-2-one and acetic anhydride, mp. 40) was dissolved in 150 ml of glacial acetic acid, mixed with 10.8 g (6.5 ml of 0.08 mol) of sulphyl chloride and stirred for 36 hours at room temperature. 45 After the addition of 30 ml of ether, the mixture is cooled to OC, the precipitate is filtered off with suction, washed with ether and dried. M.p. 204-205 ° C, you-; stroke 7.7 g (45.5% of theory) .50 PRI me R G. 9-Chloro-6-hydroxy-4H-3j1-benzoxazin-2-one. 7.6 g (31.4 mmol)) of 6-acetoxy-8-HLOR-4H-3, 1-benzoxazin-2-oria are suspended in 50 ml of methanol and mixed with 20 ml (40 mmol) of 2N at 55 gels. sodium liquor. Clear transparent solution stir for 10 minutes at natal temperature, mix with water and acidify with acetic acid. 5 The precipitate is filtered off with suction and recrystallized from isopropanol. M.p. 250s (decomposition), yield 3.3 g (52.7% of theory). Example 1-. (3,4-Dichlorophenylsulfinyl) -butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one. A solution of 1.9 g (0.01 mol) of 6-hydroxy-4, 4-dimethyl-4H-3,1-benzoxazin-2-one 4.1 g (0.0125 mol) of 4- (3,4-dichlorophenylsulfinyl) ) -butyl bromide (m.p. 63-64 ° C) in 40 ml of dimethyl sulfoxide is mixed with 3.5 g (0.025 mol) of calcium carbonate and stirred for 3 hours at 40 ° C. After cooling, it is mixed with plenty of water and extracted with chloroform. The extract is washed with water, dried with sodium sulfate, and chloroform is distilled off. The residue is recrystallized from isopropanol and diisopropyl ether. M.p. , and the yield of 1.9 g (43% theory). EXAMPLE 2. 6- (2-Phenylmercaptobutoxy) -4H-3,1-benzoxazin-2-one. To an ethanol solution of sodium ethoxide, prepared from 150, ml of ethanol and 0.92 g (9.04 mol) of sodium, was added 4.95 g (0.03 mol) of 6-hydroxy-4H-3, 1-benzoxazin-2 - It and the mixture is heated under reflux. 10 g (0.04 mol) of 4-fensch-mercaptobutyl bromide (obtained from thiophenol and excess 1,4-dibromobutane, mp. 0.03 mbar, 95-104 ° C) are added to the hot solution and heated for the next 2 h with reflux. The cooled reaction solution is taken up in ice water and extracted with acetic ester. The extract is washed with water, dried with sodium sulfate and the acetic ester is distilled off under Bakuum. The residue is recrystallized from cyclohexane and acetic ester. Mp. 96-97 ° C, yield 51.7% of theory. ° Example. (4-Chlorophenylmercapto) butoxy-4H-3,1-benzoxazIN-2-OH. Prepared analogously to Example 2 from 6-hydroxy-4H-3,1-benzoxazin-2-one and 2- (4-chlorophenylmercapto) -buttonyl chloride, prepared from 2- (4-xporpenylmer13 capto) butanol and thionyl chloride. Oil, RF ratio:. 0.25 (silica gel, petroleum ether and cyclohexane 1: 1). T. square CH-MA-S, yield 28% of theory. Example. (3,4-Dichlorophenyl mercapto) butoxy-4H-3,1-benz oxazin-2-one. Prepared analogously to example 2 of 6-OXY-4H-3,1-benzoxazin-2-one and 4- (3,4-dichlorophenylmercapto) -butyl bromide (obtained from 3,4-dichlorothiophenol and 1,4-dibromobutane, t. kip 0.1 mbar: 153-160 ° C). T, plL2 129 ° C, yield 57% of theory. PRI me R 5. 6- (4 Phenylmercapt-butoxy) -4,4-dimethyl-4H-3,1-benzox ZIN-2-OH. Prepared analogously to example 2 of 6-OXII-4,4-dimethyl-4H-3,1-benzoxazin-2-one and 4-phenylmercaptobutylbromide (t. kip 0.03 mbar: 95-104 ° C). T. square 108-109 ° С, yield 52.5% of the theory of Example 6. , 4-Dichlorophenylmercapto) -biotoxy-4,4-dimethyl-4H-3, 1-benzoxazine -2-one. Prepared analogously to example 2 of 6-hydroxy-4,4-dimesht-4H-3,1-benzoxazin-2-one and 4 (3,4-dichlorophenylmercapto) butyl bromide T. square 155-156 a yield of 53% of the theory. Example. (4-Chlorfensch 1 mercapto) butoxy} -4,4-dimethyl-4H-3, 1-benzoxazin-2-one. Creep similarly to example 2 of 6-hydroxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one and 4- (4-chlorophenylphenylmercap. then) butyl chloride. T. square 150-151 C, the yield of 55.6% of theory. Froze 6- (4-Fensh1sulphonylbutoxy) -4,4-dimethyl-4H-3,1-benz oxazin-2-one. Prepared analogously to example 1 of 6-OXII-4,4-dimethyl-4H-3,1-benzoxazin-2-one and 4-phenylsulfonylbutylbromide. T. square 57-58 s, yield 53.7% of theory. Example 9 (3 4-Dichlorophenylmercapto) -butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one. It is obtained analogously to irimer 1 from 6-hydroxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one and 4- (3,4-dichlorophenylmercapto) butylbromide (t. kip 0.1 mbar: 153-160 ° C). T. square 152-153%; yield 63.4% of theory. 2514 Example 10. (3,4-Lichlorophenylsulfinyl) -butoxy-4-ethyl-4H-3, 1-benzoxazin-2-one. Prepared analogously to example 1 of 4-ethyl-6-oxy-4H-3,1-benzoxazin-2-one and 4- (3,4-dichdorfenylsulfinyl) butyl bromide. T. square 83-84 With the release of 61.9% of theory. PRI me R 11. . (3,4-Dichlorophenylsulfinyl) -butoxy-4-isopropyl-4H-3,1-benzoxazin-2-one. Prepared analogously to example 1 of 6-OXII-4 - isopropyl-4H-3,1-benzoxazin-2-one and 4- (3,4-dichlorophenylsulfinyl) butyl bromide. T. square 73-75 C, and the yield of 48.2% of theory. Example12. 5-t4- (3,4-dichlorophenylsulfinyl) -butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one. Prepared analogously to example 1 from 5-hydroxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one and 4- (3,4-dichlorophenylsulfinyl) butyl bromide. T. square 89-90 C, the output of 73.2% of theory. Example13. Prepared analogously to example 1 from 6-hydroxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one and mesitylenesulfonate 4- (3,4-dichlorophenylsulfoxymino) -butyl bromide (T. square 170-173 ° C) / T. square 1b4-166 ° C, yield of 35.4% of theory. . Example 14 (3,., 4-Dichloro-A-acetylphenylsulfoximino) -both CHJ-4,4-dimethyl-4H-3,1-benzoxazin-He. Prepared analogously to example 1 of 6-OXII-4,4-dimethyl-4H-3,1-benzoxazin-2-one and 4- (3,4-dichloro-A-acetylphenylsulfoximino) -butyl bromide. T. square 78-79 ° C, yield 66.5%. Example 15 7.8Brom-6- 4- (4- -methylphenylmercapto) -butoxy-4,4-dimetsh-1-4H-3, 1-benzoxazin-2-one. Prepared analogously to example 1 of 7,8-dibromo-6-hydroxy-4,4-dimetsh-1-4H-3, 1-benzoxazin-2-one and 4- (4-methylphenylmercapto) -butyl chloride. T. square 114-115 ° C, yield 45.4% of theory. Example 16 6- (4-Phenylsulfinipbutoxy) -4,4,7-trimetsh-1-4H-3, 1-benzoxazin-2-one. . Psshuyut similarly to example 1 of 6-hydroxy-4,4,7-trimethyl-4H-3,1-benzoxazin-2-one and 4-phenylsulfinylbutylbromide. T. square 124-125 s, the yield of 51.6% of theory. Example 17 Prepared analogously to example 1 from 6-hydroxy-4,4,7-trimethyl-4H-3, 1-benzoxazin-2-one and 4- (3 4-dichlorophenylsulfinyl) butylbromide. T. square 151-152®С, yield 42.3% of theory. Example 18 8-Chloro-6- 4- (3,4-dichlorophenylsulfinyl) -butoxy1-4, 4-dimethyl-4H-3,1-benz-xazine -2-one. Prepared analogously to example 1 from 8-chloro-6-hydroxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one and 4- (3,4-di-chlorophenylsulfinyl) butyl bromide. T. square 121-122 ° C, yield 62.0% of theory. Example 19. 7-Chloro-6- 4- (3,4-dichlorophenylsulfinyl) -6yTpKCHj-4,4-dimethyl-4H-3,1-benzoxazin-2-one. Prepared analogously to example 1 from 7-chloro-6-hydroxy-4,4-dimethyl-H-3, 1-benzoxazin-2-one and 4- (3,4-dichlorophenylsulfinyl) butyl bromide. T. pl, 125-127 ° C, yield 41.5% of theory. PRI me R 20. 8-Chloro-6gL4- (4th tilphenylmercapto) -butoxy-4,4-dim TIL-4H-3,1-benzoxazin-2-one. Prepared analogously to example 1 of 8-ChLOR-6-OXI-4,4-dimethyl-4H-3, benzoxazin-2-one and 4- (4-methylphenium mercapto) butyl chloride. T. square 111112 With, the output of 56.0% of theory. PRI me R 21. 8-Chloro-6- (4-pheny sulfinylbutoxy) -4,4-dimethyl-4H-3, 1-benzoxazin-2-one. Prepared analogously to example 1 and 8-chloro-6-hydroxy-4,4-dimethyl-4H-3,1-benzoxazin-2-pna and 4-phenylsulfonylbutyl bromide. T. square 154-155 With, the output of 39.3% of theory. PRI me R 22. 7-Chloro-6- (4-phenyl sulfinylbutoxy) -4,4-dimetsh-1-4H-3, 1-benzoxazin-2-one. Analogously, for example, 1 is prepared from 7-chloro-6-hydroxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one and 4-phenyl 1-sulyl butylbromide. T. square 124-125 With the release of 31.5% of theory. Example 23 7-Chloro-6-C (4- (4-metsh1-phenylmercapto) -butoxy-4,14-dimethyl-4H-3; 1-benzoxazin-2-one. Prepared analogously to example 1 from 7-chloro-6-hydroxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-6a and 4- (4-ethylphenylmercapto) butyl chloride. T. square 118-119 0, yield 52.6% of the theory of Example 24. 7-Bromo-6- 4- (3,4-dichlrrphenylsulfinyl) -butoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-an. 516 Prepared as in Example 1 from 7-bromo-6-hydroxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one and 4- (3,4-d | chlorophenylsulfinyl) butyl bromide. T. square 136-138 C, and the yield of 75% of theory. PRI me R 25. 7-Bromo-6- (4-phenylsulfinylbutoxy) -4,4-dimethyl-4H-3, 1-benzoxazin-2-one. Prepared analogously to example T from 7-bromo-6-hydroxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one and 4-phenylsulphinyl; butyl bromide a. T. square 119-120 0 yield-53.1% of theory. PRI me R 26. 8-Chloro-6-4-chlorophenylmercapto) butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one. Prepared analogously to example 1 from 8-chloro-6-hydroxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one and 4- (4-chlorophenylmercapto) butyl chloride. T. square 138139 With, the yield of 56% of theory. PRI me R 27. 8-Bromo-6-G4- (3,4-dichlorophenylsulfinyl) -butoxy, 4-dimethyl-4H-3, 1-benzoxazin-2-one. , Obtained analogously to the example of 8-bromo-6-hydroxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one and 4- (3,4-dichlorophenylsulfinyl) butyl bromide. T. square , yield of 82.5% of theory, EXAMPLE 28. 8-Bromo-6- (4-phenylsulfinylbutoxy) -4,4-dimethyl-4H-3, 1-benzoxazin-2-one. Prepared analogously to example 1 from 8-bromo-6-hydroxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one and 4-phenylsulfiiyl butyl bromide. T. square 129-130 ° C, yield 44.1% of theory. Example 29 7-Chloro-6 4- (4-chlorophenylmercapto) -butoxy-4,4-dimetsh-4H-3, 1-benzoxazin-2-one. Prepared analogously to example 1. 7-chloro-6-hydroxy-4,4-dimethyl-4H-3,1-, -benzoxazin-2-one. and 4- (4-chlorophenyl mercapto) butyl chloride. square 125126 ° С, yield 45j2% theory. PRI me R, 30. 6- 4- (4-Metipfennlmerc apto) butoxy-4,4,7-trimethyl-4H-3, 1-benzoxazin-2-one. Prepared analogously to example 1 of 6-OXI-4,4,7-trimethyl-4H-3,1-benzoxazin-2-one and 4 - (- methylphenyl mercapto) butyl chloride. T. square 114-115 C, the yield of 51.9% of theory. PRI me R 31. 7-Bromo-6- 4- (4-methylphenylmercalto) -butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-Z-oH. Prepared analogously to example 1 from 7-bromo-6-hydroxy-4,4-dimesh-1-4H-3,1-benzoxazin-2-one and 4- (4-methylphenylmercaptr) -butt1chloride. T. square 122,123 ° C, yield 43.3% of theory. PRI me R 32. 8-Brom-6- 4- (4-methylphenylmercapto) -butoxy - 4, 4-dyumetsh1-4H-3, 1-benzoxazin-2-one. . Prepared analogously to example 1 from 8-bromo-6-hydroxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one and 4- (4-methyl phenylmercapto) butyl chloride. T. square 1, output 43. 3% t. eoria. Example 33 5,7-Dimethyl-6- 4- (4-methylphenylmer-capcapho) -brick of si-4H-3,1-benzoxazin-2-one, obtained as in example 1 from 5,7-dimethyl-6-hydroxy-4H-3, 1-benz oxazin-2-one and 4- (4-methylphenylmercapto) butyl chloride. T. square 107-109 yield of 28.3% of theory. Example 34 6- 4-Acetamidophenylmercapto) -butoxy-4,4,7-trimethyl-4H-3, 1-benzoxazin-2-one. Prepared analogously to example 1 from 6-hydroxy-4,4,7-trimethyl-4H-3,1-benzene zin-2-one and 4- (acetamidophenyl mercap) tr) butylme; ilata, T. square 104-106 ° C, yield 50.9% of theory. Example 35 7-Chloro-6- 4- (4th tyfphenylmercapto) -bytoxy-4H-3, 1-benzoxazin-2-one. Prepared analogously to Example 1 from 7-chloro-6-hydroxy-4H-3,1-benzoxazin-2 and 4- (4-methylphenylmercapto) -bichyl chloride. T. square 145-147 ° C, yield 44% of theory. PRI me R 36. 7-Chloro-6- (D-pheny sulfinylbutoxy) -4H-3,1-benzoxazi Prepared as in Example 1 from 7-chloro-6-hydroxy-4H-3,1-benzoxazine -2-one and 4-phenylsulfonyl butyl chloride . T. square 177-179 ° C, yield of 18.1% of theory. Pr meper 37. 5-Chloro-6- 4- (4-methylphenylmercapto) -butoxy-4H-3, 1-benzoxazin-2-one. Prepared analogously to example 1 from 5-chloro-6-hydroxy-4H-3,1-benzoxazin-2-one and 4- (4-methylphenylmercapto) -but chloride. Output 12.7% of theory. PRI me R 38. 5,7-Dichloro-6- 4- (4-methylphenylmercapto) -butoxy7-4,4-dimethyl-4H-3,1-benzoxazin-2-o Anapo1 is obtained: as described in example 1 of 5,7-dichloro-6- hydroxy-4,4-dimethyl-4H-3,1-beneoxazin-2-one and 4- (4-metip 2518 phenylmercapto) -butyl chloride. T. square 127-128 ° C, yield 50.0% of theory. Example 39 (3,4-Dichlorophenylsulfinyl) -butoxy -1,4,4-trimethyl-4H-3, 1-benzoxazin-2-one. A solution of 1.1 g (0.0025 mol) of 6-4- (3,4-dichlorophenylsulfinyl) -butoxyJ-4, 4-dimethyl-4H-3,1-benzoxazin-2-one - 1 ml of methyl iodide in 30 ml of methylene chloride mixed 30 ml 2 n. Sodium lye (0.06 mol) and a small amount (spatula tip) of tetrabutylammonium hydrogensulfate are stirred for 18 hours at room temperature. The organic phase is separated, washed twice with water, dried with sodium sulfate and distilled with methylene chloride. The residue is purified by chromatography on a column (silica gel and 40: 1 acetone). The fractions are concentrated, the residue is mixed with diisopropyl ether, the crystalline solution is sucked off and dried. T. square 90-92 ° C, yield 0.31 g (27.3% of theory). Similarly to the examples given, the following compounds can be obtained: 6- 4- (4-Bromophenylmercapto) -butoxy 4, 4-dimethyl-4H-3,1-benzoxazIN-2-OH, T. square 151-152 C. 6- (3,4-Dimethoxyphenylmercapto) -butoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one, T. square 140-142 C. 6- 4- (4-Methoxyfeyl mercapto) -butoxy-4; 4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 92-94 S. 6- 4- (4-Oxyphenylmercapto) -butoxy-4, 4-dimethyl-4H-3,1-benzo: | : Sazin-2-one, t. square 152-154 ° C. 6-T4- (4-Biphenylmercapto) -butyric | -4, 4-dimethyl-4H-3 1-benzoxazin-2-one, t. square 120-122 ° C. (3-Metoxiphenylmerkepto) -bytoxy-4,4-dimethyl-4H-3,1-benzoxazine 2-one, t. square 115-116 ° C. (3-Methylphenylmercapto) -bioxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 103-105 ° C. 6- 4- (3,5-di-tert-butyl-4-hydroxyphenylmercapto) -butoxyZ-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, t. square 8687 ° C. 6-J4- (4-Amino-3,5-dibromophenylmer-capto) -butoxy-4,4-dimetsh-1-4H-3. 1-benzoxazin-2-one, t. square 152-155 C. 6- (4-Octylmercaptobutoxy) -4, 4-dimethyl-4H-3,1-benzoxazin-2-OH. 19 Oil, RF ratio: 0.8 (silica gel: chloroform and acetone 9: 1). Calculated,%: C 67.14; H 8.96; N 3.56, S 8.15. Found: C, 67.31; H, 9.00; N, 3.57; S, 8.25. 6- (4-Cyclohexim 1 mercapta butoxy) -4,4-dimethyl-4H-3,1-benzoxazin-2-o t. square 105-107 ° C. 6- 4- (4-Methylphenylmercapto) -buto Si1-4,4-di-n-hexyl-4H-3,1-benzoxazium-2-one, t. square 76-78c. 6- 4- (4-Cyclohexylphenylmercapto) -butoxy-4,4-di-N-hexyl-4H-3, 1-benzoxazin-2-one, t. square 87-89 (3,4-Dichlorophenylmercapto) -bythoxy-4, 4-di-n-hex 1-4H-3,1-benzoxazin-2-one, t. square 63-ff4 C. 6- 4- (4-Acetamidophenylmercapto) -butoxy-4, 4-di-n hexyl - 4H-3,1 -benzoxazin-2-one, oil, RF ratio: 0.5 (silica gel plate: chloroform and ethanol 9 :one). (3,4-Dichlorophenyl mercapto) -butoxy-4,4-dicyclohexyl-4H-3, 1-benzoxazin-2-one, t. square 181-18 6- 4- (3 J 4-Dichlorophenylmerpectaco) -boxy-4, 4-dimethyl-4H-3, l-benzock Sazin-2-one, t. square 155-156 ° C. (4-Acetamidophenylmercapto) -butoxy-4, 4-dimethyl-4H-3,1-benzok sazin-2-one, t. square 158s. (2-Pyridylmercapto) -Butok-4, 4-dimethyl-4H-3,1-belzoxazin-2-one, t. square 137-138 ° C. 6- 4- (4-Cyclohexylphenylmercapto-butoxy-4,4-dimethyl-4H-3,1-benzox ZIN-2-OH, t. square 109-110 ° C. (4-Methylphenylmercapto) -buto si-4,4-dimethyl-4H-3,1 -benzoxazin-2-one, t. square 120-121 ° C. (4-Bromo-3-metsh1phenilmerkapt bytoksi-J-4,4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 129-130 ° C. (4-Optophenylmercapto) -biotoc} -4,4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 125-126 ° C. (4-Tert-butylphenylmercapto) -butoxy-4, 4-dimethyl-1H-3,1-benzok sazin-2-one, t. square 119-120 ° C. 6- (4-BenzylmerLotobutoxy) -4,4-dimethyl-4H-3, 1-benzoxazin-2-one, t. square 90-92 0. 6- (4-Methylmercaptobutoxy) -4,4-dimethyl-4H-3, 1-benzoxazin-2-one, t. square 98-99 ° C. 25 6- 4- (4-Methylphenylmercapto) -butoxy-4,4-dicyclohexyl-4H-3,1-benzox ZIN-2-OH, t. square 149-150 ° C. I 6- 4-Methylphenylmercapto) -butoxyZ-4H-3, 1-benzoxazin-2-one, t. square 125126 0. 6- 4- (4-Cyclohexylphenylmercapto) -butoxy-4,4-dicyclohexyl-4H-3,1 - benzoxazin-2-one, t. square 173-175 C. 6- 4- (4-Cyclohex1-phenylmercapto) -butoxy-4H-3, 1-benzoxazin-2-one, t. square 134-135 ° C. (4-Acetamidophenylmercapto) -butoxy-4, 4-dicyclohexyl-4H-3,1-benzoxazin-2-one, t. square 115 C (decomposition). (4-Acetamidophenylmercapto) -butoxyZ-4H-3, 1-benzoxazin-2-one, t. square 163-164 ° C. 6- 2- (3,4-Dichlorophenylmercapto) -toxy-4, 4-dimethyl-4H-3,1-benzoxazIN-2-OH, t. square 145-146 C, 6- (3,4-Dichlorophenylmercapto) -nponoKCHj-4, 4-dimethyl-4H-3,1-beisoxases. in-2-one, t. square 115-116 S. 6-C3- (4-Cyclohexylphenylmercapto) -propoxy-4,4-dimethyl-4H-3,1-benz6xazin-2-one, t. square 113-114 0. 6- 4- (3,4-Dimethylphenylmercapto) -butoxy-4H-3, 1-benzoxazin-2-one, t. square 124-125 ° C. 6- 5- (4-Cyclo-xylphenylmercapto) -pentoxy-4, 4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 108-110 ° C. 6- 5- (3,4-Dichlorophenylmercapto) -pentoxy-4, 4-dimesh-1-4H-3,1-benzoxazin-2-one, t. square 110-112 ° C. (3,4-Dimethylphenyl mercapto) -butoxy-4, 4-dimethyl-4H-3, 1-benzoxazin-2-one, t. square 122-123 0. 6-L6- (3,4-Lichlorophenylmercapto) -hexyloxy-4, 4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 102-103 C. (3,4-Dimethoxyphenylmercapto) -hexyloxy-4, 4-dimethyl-4H-3,1-benzoxazin-2-one. t. square 153-154 C. (3,4-Dichlorophenylmercapto) propoxy-4-isopropyl-4H-3,1-benzoxazin-2-one. , t square 109-1. 4- Isopropyl-6- 3- (3,4-dimethoxyphenylmercapto) propoxy} -4H-3,1-benzoxazin-2-one, t. square 102-103 S. 6- 4- (3,4-Dichlorophenylsulfimino) -butoxy 3 -4,4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 163-166 ° C. 6-L4- (3,4-Dichlop-N-p-tolysulfonylphenylsulfimino) -butoxy} -4,4-dimethyl-4H-3, 1-benzoxazin-2-one,; t. square 162-1bz S. 6- 4- (A-Bromo-3-methylphenylsulfonyl) -butoxy-4,4-dimethyl "g4Y-3,1 -b oxazin-2-one, t. square 133-134 C. 6 4- (2-Ilipidylsulfinyl) -buyok, 4-dimethyl-4H-3,1-benzoxazine -2-one, t. square 90-91 0 (decomposition). (3,4-Dichlorophenylsulfinsh1) -butoxy-4,4-dimethyl-4H-3,1-benzo-sazin-2-one, t. square 138-139c. (3,4-Dichlorophenylsulfinyl) -butoxy-4,4-dimethyl-4H-3,1-benzoxazin-2 o ", t. square 138-139 C. 6- 4- (3,4-Dichlorophenylsulfinyl) -butoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 136-139 C. 6- 4- (3,4-Dichlorophenylsulfinyl) -butoxy -1,4,4-trimethyl-4H-3,1-bevoxazin-2-one, t. square 90-92 S. 6-t4- (4-TpeT Butylphenylsulfonyl) -butoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one, t. square , 6 - - (4-Acetamidophenylsulfinyl-butoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 180 C. 6- (4-Fenilsulfinylbutoxy) -4, 4-dimethyl-4H-3,1-benz oxazin-2t. square 64-66 S. 6-C4- (4-Chlorophenylsulfinyl) -butoxy-4, 4-dimethyl-4H-3. 1-benzox ZIN-2-OH, t. square 135-136 ° C. (4-Cyclohexylphenylsulfinyl) -butoxy-4,4-di-methyl-4H-3,1-benzoxazin-2-one, t. square 147-148c 6 - ((4-MassIphenesylsulfonyl) -butoxyJ-4, 4-dimets-4H-3, 1-benzoxazin-2-one, t. square 124-125 s. 6- L4 - (4-Ft Orfe NIL sul fi nil) -butoxy-4, 4-dimethyl-4H-3,1-benzox zin-2-one, t. square 118-120 ° C. (3,4-Dimethoxyphenylsulfinyl) -butoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 157-158 C (4-Methoxyphenylsulfinyl) -butoxy-4, 4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 130-133 ° C. (4-Cxiphenylsulfinyl) -foxy-4, 4-dimethyl-4H-3, 1-benzoxazin-2-one, t, pl. 157-160 S. 6- 4- (4-Biphenylsulfinyl) -butoxy-4,4-dimethyl-4H-3,1-benzox ZIN-2-OH, t. pl, 155-157 ° C. 6-C4- (3-Methoxyphenylsulfinyl) -butoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one. Oil, RF coefficient 0,55 (pl. tink silica gel; chloroform and ethanol 9: 1), Calculated,%: C 62.51 H 6.24, N 3.47; S 7.95. q HjNOj S (403,5) Found. %: C, 62.31; H 6.17, N 3.33; S 7.84 (S- 4- (3-Methylphenylsulfin. Il) butoxy-4, 4-dimethyl-4H-3,1-benzoxazIN-2-OH, oil, RF :, 0.3 (plate silica gel: chloroform and acetone 9: 1), Calculated,%: 65 , 09 / H 6.50, N 3.6 G, S 8.27. . (387.5) Found: C 64.98, H 6.65N 3.53, S 8.30. (4-A rano-3,5-dibromophenylsulfinyl) -butoxy1-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, t. square 169172 ° C. (3,5-di-tert-Butyl-4-hydroxyphenylsulfinyl) -butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, t. square 177-179 ° C. (4-Bromophenylsulfinyl) -butoxy-4,4-dimethyl-4H-3,1-benzoxZIN-2-OH, t. square 137-138 C. (4-Methylphenylsulfinyl) -butoxy-4H-3, 1-benzoxazin-2-one, t. square 143-144 ° C. 6- (4-Cyclohexylphenylsulfinyl) -butoxy-4H-3,1 -benzoxazin-2-one, T. square 118-119 ° C. 6- 4- (4-Acetamidophenylsulfinyl) -butoxy} -4H-3, 1-benzoxazin-2-one, t. square 183-184 ° C. 6- 4- (3,4-Dimethylphenylsulfinyl) -butoxy-4H-3, 1-benzoxazin-2-one, t. square 119-120 s. 6- (4-Phenylsulfinylbutoxy) -4H-3, 1-benzoxazin-2-one, t. square 115116 ° C. . 6- 4- (3,4-Dichlorophenylsulfinyl) -butoxy-4H-3, 1-benzoxazin-2-one,. t. square 169-170 s. (4-Chlorophenylsulfinyl) -buoxy-4J-3, 1-benzoxazin-2-one,. square 169-171 ° C. 6- (4-Benzylsulfinylbutoxy) 4, 4-dimethyl-4H-3,1. - benzoxazin-2-one,. square 122 ° C. 6- (4-Methylsulfinylbutoxy) -4,4-di-ethyl-4H-3,1-benzoxazin-2-one,. square 124-126 ° C. 23 6- (4 Cyclohexylsulfonyl6ytok-4,4-dimethyl-4H-3,1-benzoxazine -2-one, t. pl, 115 ° C. 6-4 - (4-Acetamidophenylsulphinyl-butoxy-4,4-dicyclohexyl-4H-3, 1-benzoxazin-2-one, t. square 206-. 207 ° C. 6- 4- (4-Methylphenylsulfinyl) -buxy to 1-4,4-dicyclohexyl-4H-3,1-boxazin-2-one, t. square 200-201 &. 6- 4- (4-Cyclohexylphenylsulfinyl) -butoxy-4,4-dicyclohexyl-4H-3, 1-benzoxazin-2-one, t. square from 146 ° C (decomposition). 6- 4- (3,4-Dichlorophenylsulfinyl) -6yTOKCHj-4,4-dicyclohexyl-4H-3,1 -benzoxazin-2-one, t. square 186-187C 6- 4- (4-Methylphenylsulfinyl) -buxy to 2,4,4-di-n-hexyl-4H-3,1-benz oxazin-2-one, t. square 78-79; C. (4-Cyclohexylphenylsul Fin-butoxy-4,4-di-n-hexyl-4H-3,1-benzoxazin-2-one, t. square 72-75C. 6- 4- (3,4-Dichlorophenylsulfinyl) -butoxy} -4,4-di-n-ge-sil-4H-3,1-benzoxazin-2-one, t. square 83-85 C. 6-4-C4-Acetamidophenylsulfinyl-butoxy-4,4-di-n-hexyl-4H-3,1-benzoxazin-2-one, oil. RF ratio: 0.48 (silica gel plate: chloroform and ethanol - 9: 1). Calculated,%: C 67.34, H 8.12% N 4.91; S 5.62. (570.79) Found,%: C 67.52; H 7.94; N 4.95; S 5.78. (3,4-Dichlorophenylsulfinyl) ethoxyT-4,4-dimethyl-4H-3,1-benzox ZIN-2-OH, t. square 200-201 ° C. 6- 3- (3,4-Dichlorophenylsulfinyl) -propoxy | -4,4-dimethyl-4H-3,1-benz oxazin-2-one, t. square 15.7-158 ° C. 6- 3- (4-Cyclohexylphenylsulfinyl) -propoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one, oil, RF coefficient: 0.45 (silica gel plate: chloroform and ethanol 9: 1). Calculated %: C 68.00; H 7.08, N 3.17, S 7.26. C, 4, N04S (441.59) Found: C, 67.75, And 7.01, N, 3.17. S 7.13. 6- | p- (4-Cyclohexylphenylsul $ and HHrt) -pentoxy-4,4-dimethyl-4H-3,1 benzoxazin-2-one, oil, RF coefficient: 0.45 (silica gel plate: chloroform and ethanol-9: 1 ). 524 Calculated,%: C 69.05-, H 7.51, N 2.98 S 6.83. C, H ,,. (469. 65) Found: C, 70.26; H 7.74; N 2.91, S 6.87. (3,4-Dichlorophenylsulfinyl) -pentoxy-4, 4-dimethyl-4H-3, 1-benzoxazin-2-one, t. square 119-120 ° C. 4- (3,4-Dimethylphenylsulfinyl) -butoxyP-4, 4-dimethyl-4H-3,1-benzoxazIN-2-OH, t. square 13J-132 ° C. 6-b- (3,4-Dichlorophenylsulfinyl) -hexyloxy-4, 4-dimethyl-4H-3, T-benzoxazin-2-one, t. square 156-158 C. 6-b- (3,4-Dimethoxyphenylsulfinyl) -hexyloxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 131-132 C. 6-з- (3,4-Dichlorophenylsulfinip) -propoxy-4-isopropyl-4H-3,1 -benzoxazin-2-one, t. square 58-60 C. 6-. 3- (3,4-Dimethoxyphenylsulfinyl) -propoxy-4-isopropyl-4H-3,1-benzoxazin-2-one, t. square 58-60C. 4,4-Dimethyl-6- 4- (2-pyridylsulfinyl) -butoxy-4H-3,1-benz oxazin-2-one, t. square 142-143s. 6- 4- (3,4-Dichlorophenylsulfoximino) -butoxy-4,4 dimethyl-4H-3,1-benzoxazin-2-one, t. square 166-167 C. 6- (4- (3,4-Dichloro-N-methanesulfonylphenylsulfoximino) -butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, t. square 198-200 ° C. 6- 4- (3,4-Dimethoxyphenylsulfoximino) -butoxy | -4,4-dnmethyl-4H-i-3,1-benzoxazin-2-one, t. square 162ГБЗ С. . 6- C4- (4-Methoxyphenylsulfoximino) -butoxy-4,4-dimethyl-4H-3,1-benzazaz-2-one, t. square 134-140 ° C. 6- t- (4-OxyPhenylsulphoximino) butoxy-4, 4-dimetsh-1-4H-3,1-benzazazin-2-one, t. square 182-184С. (3-Methoxyphenylsulfoximio) -butoxy-4,4-dimethyl-4H-3,1-benexazin-2-one, t. square 102-105c. 6- |} 1- (4-Bifensh1sulfoximino) -buoxy-4, 4-dimetsh-1-4H-3, 1-benzoxain-2-one, t. square 184-1. 6-g 4- (4-Amino-3,5-dibronophenylsuloximino) -butoxy-4,4-dimethyl-4H3, 1-benzoxazin-2-one, t. square 206-. . (3,5-di-trvt. Butyl-4-hydroxy-. Ensh (sulfoxyK1ino); butoxy-4,4 dimethyl-4H-3, -benzoxazin-2-one,. square 176-178 ° C. (3-Methylphenylsulfoximino) -butoxy-4, A-dimethyl-4H-3,1-benzox zin-2-one, t. square 118-120 ° C. 6-4- (4-F. torphenylsulfoximino) | -butrxy | -4, 4-dimethyl-4D-3,1-benzox. Zin-2-one, t. pl, 136-138 ° C. 6-4-C4-Bromophenylsulfonic-imino) -bytokox-4, 4-dimethyl-4H-3, 1-benzko ZIN-2-OH, t. pl, 155-157 ° C. (4-Bromo-3-methylphenylsulphoximino) -butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, t. square 1536-4- (4-Cyclohexylphenylsulfoxy-mino) -butoxy-4,4-dimethyl-4H-3,1 -benzoxazin-2-one, t. square 168-169 C. 6- (fj- (4-Methylphenyl sulfoximino) -butoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 147-148 C. 6- (4-Phenylsulfoximinobutoxy) -4 4-dimethyl-4H-3,1-benzoxazin-2-about 6- 4- (4-Chlorophenylsulfoxymino) -butoxy-4,4-dimethyl-4H-3,1-benzozacazine -2-he, t. square 132 ° C. B-p- (4-toet, Butylphenylsulfox-mino) -butoxy-4,4-dimethyl-4H-3,1 -benzoxazin-2-one, t. square 187s. 6- 4- (4-aceta-dophenylsulfonic but) butoxy-4,4-dimethyl-4H-3,1-ben oxazin-2-one, t. square 185 ° C. (4-Methylphenylsulfoximino) -butoxy-4,4-di-n-hexyl-4H 3, 1-benzoxazin-2-one, t. square 89-91 S. 6- {4- (A-Cyclohexylphenylsulfoxy mine) -butoxy-4,4-di-and-hexyl-4. H, -3,1-benzoxazin-2-one, t. mp 78-80 ° C (3,4-Dichlorophenylsulfoximino) -butoxy-4,4-di-n-hexyl-4H-3, 1-benzoxazin-2-one, t. square 1066-4- (4-Acetamidophenylmercapto) mino) -butoxy-4,4-di-n-hexyl-4J-3, 1-benzoxazin-2-one, t. square 146148 ° C. 6-L4- (4-Acetamidophenylsulphoxy but) -butoxyJ-4,4-dicyclohexyl-4H-3, 1-benzochsazin-2-one, t. square 149150 ° C. 6-14- (4-Methylphenylsulphoximino) -butoxy-4,4-dicyclohexyl-4H-3,1. - benzoxazin-2-one, t. square 176-177с (4-Cyclohexylphenylsulphoxymino) -butoxy J-4,4-dicyclohexyl-4H3, 1-benzoxazin-2-one, t. square 219220 ° C. (4-Methylphenylsulphoximino) -butoxy-4H-3, 1-benzoxazin-2-one, t. square 153-154 C. 6-G4- (4-Cy1 loghexylphenylsulfoximino) -butoxy-4H-3,1-benzoxazin-2-one, t. square 187-188 ° C. 6-G4- (4-Acetamidophenylsulfoxy but) -butoxy-4H-3,1-benzoxazin-2-one, t. square 135-137 ° C. 6- 5- (3,4-, 1-chlorophenylsulfoximino) -pentoxy-4,4-dimethyl-4H-3,1-benz oxazin-2-one, t. square 169-170 C. 6- | 5- (4-Cyclohexylphenylsulfoximino) pentoxy-4,4-dimethyl-4H-3,1-benzoxazin-2 on, t. square 110-111 S. (3,4-Dichlorophenylsulphoximino) -propoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, t. square 135-136 S. (4-Cyclohexylphenylsulphoximino) -propoxy-4, 4-dimethyl-4H-3. . 1-benzoxazin-2-one, t. square 175-170 0. (3,4-Dichlorophenylsulphoximino) is 1ssi-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, t. square 139-140 ° C. 6- (4-Cyclohexylsulfoxyminobutoxy) -4,4-dimethyl-4 -3,1-benzoxazIN-2-OH, t. square 108-110 ° C. 6- (4-Benzylsulfoxyminobutoxy) -4, 4-dimethyl-4H-3 ,. 1-benzoxazin-2-one, t. square 132-138 ° C, 6- (4-n-Octylsulfoxin-butoxy) -4,4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 182 ° C. (4-Cyclohexylphenylmecapo) -butoxy-4,4-DIETHYL-4N-3,1-benzksazin-2-one, t. square 85-88 ° C. 6- C4- (3,4-Dichlorophenylmercapto) butoxy-4, 4-DIETHIL-4H-3,1-benzox-IN-2-OH, t. square 143-145 0. 6- (4-Phenylsulfoximinobutoxy) DIETHIL-4H-3, 1-benzoxazin-2-one,. square . 104-106 ° C. 6 - 4 - (3,4-Dimethylphenylmercapto) butoxy-4, 4-DIETHIL-4H-3,1tbenzxazin-2-one, t. square 124-125 C. (3,4-Dimethoxyphenylmercapto) butoxy-4,4-DIETHIL - 4H-3,1-benzox IN-2-OH, t. square 110-111 0. 6-4- (4-Acetamidofvnilmercapto) butoxy-4H-3, 1-benzoxazin-2-one,. square 117-119 0. 6-Ь4- (4-Methylphenylmercapto) -buoxy-4-methyl-4H-3, 1-benzoxazin2-one, t. square 111-113 0. (4-Acetamidophenylmercapto) butoxy-4-methyl-4H-3, 1-benzoxazin2-one, t. square 122-124 ° 0. (2-Kenzthiazolnlmercapto; -butoxy-4,4-dimethyl-4H-3,. 1 -beizoxazin-2-one, t. mp 183-134 ° C. 6- 4- (4,6-Dimethyl-2-pyrimidinyl capto) -butoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 125-127 C. 6- 4- (1-oxide-2-pyridylmercapto-butoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 154-156 S. (2,2,4-Triazol-3-yl-mercapt -butoxy-4,4-dimethyl-4H-3,1-benzozk ZIN-2-OH, t. square 181-183 S. 6- 4- (2-Pyrimidinylmercapto) -butoxy-4, 4-dimethyl-4H-3 1-benzoks ZIN-2-OH, t. square 142-144 ° G. 6-G4- (4-Pyridylmercapto) -butoxy1-4, 4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 153-155 ° C. 8- 4- (4-Cyclohexylphenylmercapto-butoxy-4,4-dimethyl-4H-3,1-benzalkasin-2-one, t. square 109-110 ° C. 8- 4- (3,4-Dichlorophenylmercapto) -butoxy-4,4-dimethyl-4H-3,1-benzok ZIN-2-OH, t. square 137-138 ° C. 8- (4-Phenylmercaptobutoxy) -4,4-dimethyl-4H-3, 1-benzoxazin-2-one, t. square 98-1U S. 8- 4- (3,4-Dimethylphenylmercapto) -butoxy-4; 4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 137-139 ° C. 8- 4- (3,4-Dimethoxyfensch1 mercapto-butoxy-4,4-dimethyl-4H-3,1-benzalkasin-2-one, t. square 116-117C. (4-Acetamidophensh1 mercapto) -6yroKCii-4,4-dimethyl-4H-3,1 -benzoxazin-2-one, t. square 166-167 C. 6 - {% - (3,4-Dimethylphenylmercapto) -butoxy-7-nitro-4, 4-dimethyl-4H-3, 1-benzoxazin-2-one. Oil, RF ratio: 0.4 PLA chloroform and ethatink silica gel NOL 9: 1). Calculated,%: C. 61.38; H 6.09; N 6.51; S 7.45. , / CyH NOj-S (430.52); Found: C, 61.10; H 6.07; N 6.24; S 7.28. (4-Acetamidophenylmercapto) -butoxy-7-nitro-4, 4-dimethyl-4H-3-benzoxazin-2-one, t. Pl / 203-205. 6- 4- (4-Chlorophenylmercapto) -butoxy-7-nitro-4 4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 155-156 seconds 6- 4- (2-Pyridyl mercapto) -butoxy-J-7-nitro-4, 4-dimethyl-4,4-3,1-benzoxazin-2-one, t. square 98-100 C. (4-Methylphenylmercapto) butoxy-7-nitro-4, 4-dnmethyl-4H-3,1 -benzoxazin-2-one, t. square 128-129 C. 6-t4- (3,4-Dimethoxiphenylmercapto) -butycoxyJ-7-iptro-4,4-dimethyl-411-3, 1-benzoxazin-2-one, t. square 115 (3,4-Dimethylphenylmercapto) -butoxy-4, 4-dimethyl-4H-3, -benzoxazin-2-one, t. square 120-122 C. (4-Acetamido Fekilmercapto) -butoxy-4, 4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 162-162 C. 7- 4- (2-Pyridylmercapto) -butoxy-4, 4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 125-127 ° C. 7- f - (4-Methylphenylmercapto) -butoxy-4, 4-dimethyl-4,4-3,1-benzoxazin-2-one, t. square 120-122®C. 7- 4- (4-Chlorophenylmercapto) -butoxy} -4,4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 117-119 ° C. 7- 4- (3,4-Dichlorophenylmercapto) -butoxy-4, 4-dimethyl-4H-3,1-benzoxazIN-2-OH, t. square 104-106 ° C; 7- (4-Phenylmercaptobutoxy) -4, 4-dimethyl-4H-3, 1-benz oxazin-2-OH, t; pl. 123-125 ° C. (3,4-dimethoxyphenylmercapto) butoxy-4, 4-dimethyl-4H-3,1-benzoxazin-2-one. Oil, RF ratio: 0.6 (silica gel plate: ethylene chloride and ethanol 9: 1). Calculated,%: C 63.29; H 6.52; N3.35. . , N, jOg-S. (417.53) Found,%: C 63.00; H 6.54; N 3.38. (4-Methylphenylmercapto) butoxy-4, 4,8-trimethyl-4H-3,1-benzoxazin-2-one, t. square 125-12bs. (3,4-Dichlorophenyl mercapto) butoxy-4,4,8-trimethyl-4H-3,1-benzoxazin-2-one, t. square 130-1 J7c. (4-Acetamidophenylmercapto) -butoxy-4, 4,8-trimethyl-4H-3,1-benzoxazin-2-one, t. square 167-168 S. 6- (H- (2-Pyridylmercapto) -butoxy-4; 4,8-trimetesh-1-4H-3,1-benzoxazIN-2-OH, t. square 144-145 ° C. (4-Chlorophenylmercapto) butoxy-4, 4-8-trimethyl-4H-3,1-benzoxOZIN-2-OH, t. square 141-142 ° C. 6- (4-Phenylmercaptobutoxy) -4,4,9-trimethyl-4H-3, 1-benzoxazin-2-one, t. square 125-126 ° C. (3,4-Dimethylphenylmercapto) -butoxy} -4, 4,8-trimethyl-4H-3,1-benzoxazin-2-one, t. square 146-147 C (3,4-Dimethoxyphenylmercapt 6yTOKCHj-4,4,8-trimethyl-4H-3,1-ben oxazin-2-one, t. square 130-131 C. (3,4-Dichlorophenylsulfinyl) -butoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 82-84 ° C. 7- (4-Phenylsulfinshbutoxy) -4, 4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 117-119 ° C. Hydrate (3,4-dimethylphenylsnyl) -butytoxy 4,4-dimethyl-4H-; -3,1-benzoxazin-2-one. Oil, RF ratio: 0.6 (silica gel: ethylene chloride and ethanol 9: 1). Calculated,%: C 62.98, H 6.97-, N 3.34; S 7.64. , . С Н N0 S (419.54) Found,%: С 63, H 6.85-, N 3.40; S 7.64. 7- 3- (4-Acetamidophenylsulfinyl-butoxy | -4,4-dimethyl-4H-3, 1-benzo ZIN-2-OH, t. square 145-147 ° C. 7-G4- (2-Pyridylsulfinyl) -bottom, 4-dimethyl-4H-3,1-benzoxazine -2-one. t. pl, 153-155 ° C. (4-Methylphenylsulfinyl) -buxy-4,4-dimethyl-4H-3,1-benzox ZIN-2-OH, t. square 128-130 ° C. 7- 4- (4-Chlorophenylsulfinyl) -but Si1-4,4-dimethyl-4H-3,1-benzoxazine -2-one, t. square 140-142 ° C. 7-; 4g (3,4-Dimethoxyphenylsulfinyl) butoxy | -4,4-dimesh1-4H-3,1 -benzoxazin-2-one. Resin, RF ratio: 0.4 (silica gel: ethylene chloride and ethanol 9: 1). Calculated by. %: C 60.95; H 6.28; 3.23; S 7.40. . S X433 53) Found,%: C 60.70; H 6.25; N 3.03; From 7.53. 8- 4- (4-Cyclohexylphenylsulfinyl) -butoxy-4,4-dimethyl-4H-3,1 benzoxazin-2-one, t. square 144-145 C. 8- 4- (3,4-Dichlorophenylsulfinsh1) -butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, t. square 113-114 C. 8- (4-Phenylsulfinylbutoxy) -4,4-dimethyl-4H-3,1-benzoxazin-2-one, T. . Submarine J6 -163 ° C. 8-4- (4-Acetamidophenylsulfinyl-butoxy3-4. , 4-dimethyl-4H-3,1-benzoxysn-2-oa, t. square 166-167 C. (3,4-Dimethylphenylsulfinyl) -butoxy-4,4-dimethyl-4H-3,1 benzoxazin-2-one, t. square 111-112 C. 8-t4- (3,4-Dimethoxiphenylsulfinyl) -butoxy 3 -4,4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 102-103 S. 6- 4- (4-Cyclohexylphenylsulfinyl) -butoxy-4,4-diethyl-4n-3,1t benzoxazin-2-one, t. square 168-170 C. 6- (3,4-Dichlorophenylsulfinyl) -butoxy-4,4-diethyl-4H-3, 1-benzoxazin-2-one, t. square 91-93c, 6- (4-Phenylsulfinylbutoxy) -4, 4-diethyl-4H-3,1-benzoxazin-2-one. I Resin, RF coefficient: 0.6 (silica gel plate: chloroform and ethanol 9: 1). Calculated,%: C 65.8li, H 6.78; 3 49; S 7.98. C, Hj, NO4S (401.53); Found: C, 65.55; H, 6.75; N, 3.40; S 7.71. (3,4-Dimethylphenylsulfonyl) -butoxy-4, 4-diethyl-4K-3,1-benzoxAZIN-2-OH, t. square 137-138 ° C. 6- (3,4-Dimethoxyphenylsulfinyl) -butoxy-4, 4-diethyl-4H-3,1-benzoxazIN-2-OH, t. square 161-163 ° C. 6- 4- (4-Acetamidophenylsulfinyl) -butoxy 4-DIETHIL-4H-3,1-benzoxazIN-2-OH, t. square 69-70 ° C. 6-G4- (4-Pyridylsulfinyl) -bott IW -4,4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 141-143 C. 6- 4- (4,6-Dimethyl-2-pyrimidinesulfinyl) -butoxy-4,4-dimetsh-1-4-4H-3, 1-benzoxazin-2-one. Resin, RF ratio: 0.4 (silica gel plate: ethylene chloride and ethanol 9: 1). Calculated,%: C 59V53; H 6.25; S 7.95 (403.50) C 59.30) H 5.99 Found, / S 7.88. (3,4-Dichlorophenylsulfinyl) butoxy-4-methyl-4H-3, 1-benzoxazin-2-one, t. square 138-139 ° C. 6- 4- (4-Methylphenylsulfinyl) -butoxy-4-methyl-4H-3, 1-benzoxazin-2-one, t. square 120-121 ° C. (4-Acetamidophenylsulfinsh1) -butoxy-4-methyl-4H-3, 1-benzoxazin-2-one, t. square 124-12bs. (4-Acetamidophenylsulfinyl) butoxy-7-nitro-4, 4-dimethyl-4H-3,1-benzoxazin-2-one, t. square 240-24 lc 6- 4- (4-Chlorophenylsulfinyl) -butoxyT-7-nitro-4,4-dimethyl-4H-3, .1-benzoxazin-2-one, so pl. 159-160C. (2g Pyridylsulfinyl) -butoxy1-7-nitro-4, 4-dimethyl-4H-3,1-benz-5 oxazin-2-one, so pl. 156-157 ° C. . 6- 4- (4-Methylphenylsulfinsh1) -butoxy1-7-nitro-4, 4-dimethyl-4H-3,1-: benzoxazin-2-one, so pl. 176-177 C. (3,4-Limethoxyphenylsulphonyl) -butoxy-7-nitro-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, mp 190192 C. 6- 4- (3,4-Dimethylphenylsulfinsh1) -butoxyT 7-nitro-4, 4-dimethyl-4H-15 -3,1-benzoxazin-2-one, so pl. 146147 ° C. 8-Chloro-6- 4- (methylphenylsulfinyl) -butoxy1-4, 4-dimethyl-4H-3,1-benzoxazin-2-one, mp, 113-114 C.20 7-Chloro-6- 4- (4-Methylphenylsulfinyl) -butoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one, so pl. 143-144 C. 6- 4- (4-Chlorophenylsulfinyl) -brick-25 Si1-8-chloro-4,4-dimethyl-4H-3,1-benzoxazin-2-one, so pl. 83-85 C. 6- 4- (4-Chlorophenylsulfinyl) -butoxy-7-chloro-4, 4-dimethyl-4H-3.1-benzoxazin-2-one, mp. 162-163 S. zo 7-Bromo-6- 4- (4-methylphenylsulfinyl) -butoxy-4,4-dimethyl-4I-3,1-benzoxazin-2-one, so pl. 143-145 ° C. 8-Bromo-6-4-methylphenylsulfinyl) -butoxy-4, 4-dimethyl-4H-3,1 - benz-, oxazin-2-one, so pl. 123-124 S. 6- (4-Methylphenylsulfinyl) -butoxy 4, 4,7-trimethyl-4H-3,1-benzoxazin-2-one, mp. 152-153 ° C. 7,8-Dibromo-6- 4- (4-Methylphensh1sul- 0 finil) -butoxy} -4,4-dimethyl-4H-3,1 - .. -benzoxazin-2-one, so pl. 138-139 0. (3,4-Dichlorophenylsulfinsh1) -butoxy-4,4,8-trimethyl-4H-3,1-benzoxazin-2-one, so pl. .158 ° C. (4-Methylphensh1Sulfinyl) -butoxy-4, 4,8-trimethyl-4H-3,1-benzoxaz in-2-one, so pl. 137-138 ° C. (4-Chlorofensch 1sulphinyl) -bu-jg, 4,8-trimetsh-1-4H-3,1-benzoxazin-2-one 163-164 0. 6-.C4- (3,4-Dimethoxyfensch1sulfinyl) -butox3-8-trimethyl-4H-3, L-benzoxazin-2-one, so pl. 142-143 0. 55 6- (4- (3,4-.Cymethylphenylsulfinyl) butoxy-4,4,8-trimeish-1-4I-3,1-benzoxazin-2-one, mp 113-114 ° C. 6- (4-Phenylsulfinylbutoxy) -4, 4,8-trimethyl-4H-3.1-benzoxazin-2-one, mp. 143-144s. 6-G4- (4-Acetamidophenylsulfinyl) -butoxy-4, 4,8-trimeish-1-4H-3,1-benzoxazin-2-one, so pl. 212-213 C. 6- 4- (2-Pyridylsulfinyl) -butoxy-4; 4,8-trimethyl-4H-3.1-benzoxazIN-2-OH; mp. 163-164 0. 8-Chloro-6- 4- (4-methylphenylsulfinyl) -butoxy-4H-3,1-benzoxazin-2-one, so pl. 114-115 s. 6- 4- (4-Acetamidophenylsulfinyl) -butoxy) -4,4,7-trimethyl-4H-3,1 -benzoxazin-2-one, so pl. 210-211 ° C. (4-Methylphenylsulfinyl) -butoxy-4,4,7-trimethyl-4H-3,1-benzox-ZIN-2-OH; 152-153 p. 8-Chloro-6- 4- (4-Acetamidophenylsulfini) -butoxy-4H-3.1-benzoxazin-2-one, so pl. 130-132 ° C. 6- 4- (4-Methylphenylsulfinyl) -butoxy-5, 7-dimethyl-4H-3, 1-benzoxazIN-2-OH, so pl. 114-116 ° C. 6- 4- (3,4-Dichlorophenesulfinyl) -butoxy-5, 7-dimethyl-4H-3,1-benzoxazin-2-one, mp 126-128 ° C. 7-Chloro-6- |} - (4-metshphenylsulfonyl) - botoxy-4H-3, 1-benzoxazin-2-one, so pl. 177-178 ° C. 5-chlorop-6-t4- (4-methylphenylsulfinyl) -butoxy-4H-3,1-benzoxazin-2-one, so pl. 183-185 ° C. 5,7-Dichloro-6- 4- (4-methylphenylsulinyl) -butoxy-4,4-dimetsh-1-4H-3.1benzoxazin-2-one, so pl. 169-170 C. 5,7-Dichloro-6- (4H1) ynylsulfinsh1butoxy) -4,4-dimethyl-4H-3,1-benzoxazIN-2-OH, so pl. 186-187s. 6- 4- (2-Benzthiazolsh1sulfonsh1) -butoxy-4, 4-dimethyl-4H-3, 1-benzokazin-2-one, so pl. 177-179 C. 6-: 4- (1,2,4-Triazol-1-3-sulfonyl) -butoxy-4,4-dimethyl-4H-3,1-benzazaz-2-one, mp. 197-199s 6-14- (2-11irimidinsulfonyl) -buoxyZ-4, 4-dimethyl-4H-3,1-benzoxAZIN-2-OH, so pl. 184-18bS. 5- 4- (3,4-Dichlorophenylsulfoximino) -butoxy-4,4-dimethyl-4H-3, t-benzoxazin-2-one, mp. 127-128 C. 7-L4- (3,4-Dichlorophenylsulfoximino) -butox-3,4-dimethyl-4H-3,1-benzoxazin-2-one. Resin ratio. RF: 0.4 (plaque silica gel: ethylene chloride ethanol 9: 1). Calculated,%: C 52.52 - H 4.85; Cf 15.50i N 6.12; S 7.01. CIJ-} 04S (457.39); Found: C, 52.34 H, 4.80; a 15.50; N 6.16; S 7.01. 7- 4- (3,4-Limethylphenylsulfoxy: mino) -butoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one, m.p. 161-163 pp. 7-, 4- (4-Methylphenylsulfoxymino-butoxy-4,4-dimethyl-4H-3,1-benzcoxazin-2-one, mp: 122-124 ° C. (4-Chlorophenylsulfoxymino ) -6yTOKCHj-4,4-dimesh1-4H-3,1 benzoxazin-2-one, mp 103-105 C. 7- (4-Phenylsulfoximinobutoxy) -4, 4-dimethyl-4H-3,1-benzoxazine -2-one, mp. 130-132 ° C. (3,4-Dimethoxyphenylsulfox mino) -butoxyZ-4,4-dimethyl-4H-3,1-benzoxazin-2-one, mp 110- G12 S. (4-Cyclohexylphenylsulphox mino) -butoxy-4,4-dimethyl-4H-3,1 -benzoxazin-2-one, mp 115-116 C. (3,4-Limethylphenylsulfoximino) -buttori -4 , 4-dimethyl-4H-3,1 -benzoxazin-2-one, mp 130-131 0. 8- 4- (3,4: -Dichlorophenylsulfoximino) -butoxy 3-4,4- dimethyl-4H-3,1. -benzoxazin-2-one, mp 144-145 C. 8- (4-Phenylsulfoximinobutoxy) -4, 4-dimethyl-4H-3,1-benzoxazin-2-one, mp 103-104 ° C. (3,4-Limethoxyphenylsulphoxy mino) butoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one, mp 120-121 pp. 8- 4- (4-Acetamidophenylsulfonyl Ho) -6yTOKcifj-4,4-dimethyl-4H-3,1 -benzoxazin-2-one, mp; 166-167 C. 6-J4- (3,4-Dimethylphenylsulfoximino) - butoxy -, 4,4-DIETHIL-4N-3,1 -benzoxazin-2-one, so pl. 104-105 C. 6- 4- (3,4-Limethoxyphenylsulfoxy mino) -butoxy-4,4-DIETHIL-4H-3,1 benzoxazin-2-one, so pl. 93 - 95 ° C. / (4-Cyclohexylphenylsulfoxy-mino) -butoxy-4,4-DIETHYL-4H-3,1-ben oxazin-2-one, m.p. 158-160 C. (4-Acetamidophenylsulphoxy mino) -butoxy4-4,4-diethyl-4H-3,1 -benzoxazin-2-one, mp. 144-146 C. 6- 4- (3,4-Dichlorophenylsulfonoxy no) -butox I-4,4-diethyl-4H-3, 1-benz oxazin-2 he, so pl. 136-138 C. 6- (4-Pheunsulfoximbobutoxy) -4, 4-DIETSH1-4H-3,17 benzoxazin-2-one so pl. 134-135 ° C. 6-. (3,4-Dichlorophenylsulphoximino) -butoxy-4-methyl-4H-3,1-benzoxazin-2 it, so pl. 179-180s. 6- 4- (4-Methylphenylsulphoximino) -butoxy-4-methyl-4H-3, 1-benzoxazIN-2-OH, mp. 121-123 0. (4-Acetamidophenylsulphoxymino) -butoxy-4-methyl-4H-3,1-benzoxazin-2-one, mp. 123-125 0. (3,4-Dimethyl-N-acetylphenylsulfoximino) -butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, m.p. 151153 ° C. (4-Acetamido-N-acetylphenylsulfoximino) -butoxy-4,4-dimethyl-4I-3, 1.-benzoxazin-2-one, so pl. 136138 S. (4-Methyl-N-acetylphenylsulfoximino) -butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, mp. 142144 ° C. 7- (4- (4-Chloro-M-acetylphenylsulfoximino) -butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, mp 127129 ° C. (3,4-Dichloro N-acetylphenylsulphoxymino) butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, mp 130132c. (N-acetylphenylsulfonic-4) dimethyl-4,4-dimethyl-4n-3, 1 -benzoxazin-2-one, mp 123-125s. 7-4- (3,4-dimethoxy-N-acetylphenylsulfoximino) butoxy-4,4-dimethyl-4H-3, 1-benzoxazine 2-one, mp 202-204 ° C. (4-Cyclohexyl-VI-acetylphenylsulfoximino) -butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, mp. 167-168 C. ( 3,4-Lichloro-N-acetylphenylsulfoxymino) butoxymino) butoxy-4, 4-dimethyl-4H-3,1-benzoxazin--2 - he, so pl. 170-171 ° C. 8- 4- (3,4-Dimethyl-1-acetylphenylsulfoximino) -butoxy | -4,4-dimethyl-4H-3, 1-benzoxazin-2-one, mp. 145146 ° C. (M-Acetylphenylsulfoximino) -butoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one, so pl. 113-114 ° C. 8-.4- (3,4-Dimethoxy-N-acetylphenylsulphoxymino) -butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, mp.137138 ° C. (4-Hcetamido-N-acetylphenylsulfoxymino) -butoxy3-4,4-dimethyl-,. 4H-3,1 -benzoxazin-2-one, t. 35 (4-Cyclohexyl-M-acetylphenylsulfoximino) -butoxy-4,4-diETSH1-AN-3, 1-benzoxazin-2-one, so pl. 176-178 ° C. 6- 4- (3,4-Dimethyl-N-acetylphenyl sulfoxymino) butoxy-4,4-diethyl-4H-3, 1-benzoxazin-2-one. Resin, RF ratio: 0.52 (mp zinc silica: chloroform and ethanol 9: 1). C, 64.17; H 7.04; Calculated;, N, 5.76; S 6.59. (486.64) C 63.90; H 6.90 Found, / 5.51; S 6.94. (4-Acetamido-N-acetylphenyl sulfoxymino) -butoxy-4,4-diethyl-4H-3, 1-benzoxazin-2-one, mp.146149 ° C. (3,4-Dimethoxy-N-acetylphen. SulAoximino) -butoxy-4,4-diethyl-4H-3, 1-benzoxazin-2-one. Resin, RF ratio: 0.5 (silica gel plate, chloroform and ethanol 9: 1). Calculated,%: C 60.21, H 6.61, N 5.40, S 6.18. (518.64) Found,%: C 59.95, H 6.58; N 5.19; S 6.31. (3,4-Dichloro-N-acetylphenylsulphoxymino) -butoxy-4,4-diethyl-4H-3, 1-benzoxazin-2-one, mp 166166 ° C. ((-Acetylphenylsulphoximino) -butoxyZ-4,4-DIETHIL-4H-3,1-benzoxazin-2-one, mp 120-122 C. 7- (4-Phenylsulphoxyminobutoxy) -4, 4-dimethyl-4H -3,1-benzoxazin-2-about 6- 4- (3,4-Dimethoxyphenylsulfoximino) -butoxy-4,4,8-trimethyl-4H-3, 1-benzoxazin-2-one, mp 175756 ° C. 6-; 4- (3,4-Dimethylphenylsulfoxy-yno) butoxy-4,4,8-trimethyl-4H-3, 1-benzoxazin-2-one, mp 175 ° C. 6- (4 -Phenylsulfoximinobutoken -4,4,8-trimetesh1-4H-3,1-benzoxazin-2-one mp 147-148 ° C. 6-4- (3,4-Dichlorophenylsulfoxime but -butoxy-4.4) , 8-trimethyl-4H-3.1-benzoxazin-2-one, mp. 116-117 C. (4-Chlorophenylsulfoximino) -butoxy} -4, A, 8-trimethyl-4H-3,1-ben | o 167-168 p. 5 6- 4- (4-Metsh1phenylsulfoximino) -butoxy-4, 4,4 | 8-trimethyl-4H-3,1-benzoxazin-2-one, mp 183-184 c. 6- 4- (4-Acetamidophenylsulphoxymino) -butoxy-4,4,8-trimethyl-4H-3, 1-benzoxazin-2-one, mp 168169 C. (4 -Acetamidophenylsulphoximino) -butoxy3-4,4-dimethyl-7-nitro-4H-3, 1-benzoxazin-2-one, mp 209211 ° C. (4-Chlorophenylsulfoximino) -butoxy-4, 4-dimethyl 7-nitro-4H-3, 1-benzoxazin-2-one, so pl. 116118 ° C. 6- 4- (4-Metsh1phenylsulfoximino) -butoxy-4, 4-dimethyl-7-nitro-4H-3,1 -benzoxazin-2-one, so pl. 112-114C. 6- (3,4-Dimethoxyphenylsulfoximino) butoxy-4,4-dimethyl-7-nitro 4H-3, 1-benzoxazin-2-one, mp. 147-149 ° C. (3,4-Limethylphenylsulfoximino) -butoxy-4,4-dimethyl-7-nitro-4H-3, 1-benzoxazin-2-one, mp.145146 ° C. 8-Chloro-6- 4- (3,4-dichlorophenylsulfoximino) -butoxy-4,4-dimethyl-4H-3, 1-benzoxayin-2-one, so pl. 135136 S. 7-Chloro-6- 4- (3,4-dichlorophenylsulfoximino) -butoxy-4,4-dimethyl-4H-3 .1-benzoxazin-2-one, m.p. - 87 ° C. 8-Chloro-6- 4- (4-methylphenylsulfophenimine) -4.4-dimethyl-4H-3, 1-benzoxazin-2-one, m.p. 132133 ° C. 8-Chloro-6- 4- (4-chlorophenylsulfoximino) butoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one, m.p. 162-163 0. 7-Chloro-6-L4- (4-x: 1orfe NILE sulbfoxymino) -butoxy-4,4-dimesh-1-4H-3, 1-benzoxazin-2-one, m.p. 132133 ° C. (3,4-Dichlorophenylsulphoximino) -butoxy 4,4,7-trimethyl-4H-3, 1-benzoxazin-2-one, mp 135357 ° C. 6- (4-Fensh1sulfoximinobut6ksi) -5, 5,7-trimethyl-4H-3,1-benzox-Jin-2-one, m.p. 123-124 ° C. . 6- 4- (4-Methylphenylsulphoximino) butoxy-4; 4,7-trimethyl-4H-3,1 benzoxazin-2-one; mp. 153-154 ° C. 6-C4- (4-Acetamido-M-acetylphenylsulfoxymino) -butoxy-7-nitro-4,4-dimethyl-4H-3, 1-bsnzoksazin-2-one, so pl. 250-2.52 ° C. 6- 4- (4-Chloro-H-acetylphenylsulpho-ximino) -butoxy-7-nitro-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, mp 21 213 ° C. 5- 4- (4-Methyl-N-acetic acid, ximino) -butoxy-7-nitro-4,4-dimethyl-4H-3,1-benzoxazin-2-one, mp.214216 ° C 6-4 - (3,4-Dimethoxy-N-acetylphenylsulfoximino) -butoxy-7-nitro-4, 4-dimethyl-4H-3,1-benzoxazin-2-one so pl. 120-122 ° C. , 4-Dimethoxy-N-acetic acid, phenyl sulfonicimino) -butoxy-4,4,8-trimethyl-4H-3, 1-benzoxazin-2-one, so pl. 123-124 ° C. 6- 4- (3,4-Dimethyl-α-acetylphenyLsulfoximino) -butoxy-4,4,8-trimethyl-4H-3, 1-benzoxazin-2-one, mp 14.14 ° C. (N Lethylphenylsulfoxymino-butoxy-4,4,8-trimethyl-4H-3,1-benz oxazin-2-one, mp. 9E-100 ° C. (3,4-Dichloro-N-acetylphenylsulfoximino) -butoxy -4,4,8-trimethyl-4H-3, 1-benzoxazin-2-one, t; mp 140-141 ° C. (4-Chloro-H-acetylphenylsulphoximino) -butoxy -4,4,8- trimethyl-4I-3,1-benzoxazin-2-one, mp 178-179 6- 4- (4 - Acetamidophenylsulfoximino) -butoxy-4,4,7-trimethyl-4H-3,1-benzoxazine- 2-one, mp 159-161 C1 (3,4-Dichloro-1-p-toluenesulfonne-phenylsulfoximino) -butoxy-4, 4-dimethyl-4H-3,1-benzoxazine. -2-one, t. mp 174-175 C. 6- 4- (3,4-Dichloro-N-benzoylphenylsulphoxymino) -toxy-4,4-dimethyl-4FI-3, 1-benzoxazin-2-o , mp 189190 ° C. 6- 4- (3,4-Dimethoxy-N-acetylphenyl sulfoxymino) -butoxy-4,4-dimethyl. -4H-3,1-benzoxazin-2-one, mp 155, 157 ° C. (4-Phenyl-N-acetylphenylsulf ximino) -butoxy-4,4-dimethyl-4H-3,1 -benzoxazin-2-one, mp 106-108 ° C. (3 , 5-di-tert. Butyl-4-hydroxy-acetylphenylsulphoxyimino) -butoxy-4, 4-dimethyl-4H-3,1-benz oxazin-2-one mp 206-207 C. (4-Amino -3,5-dibromo-H-aceo-tylphenylsulfoximino) -butoxy-4,4, dimethyl-4H-3.1-benzoxazin-2-one, mp. 19 8-2 00 ° C. 1 2538 6- 4- (4-tert, Butyl-N-acetylphenylsulfoximino) -butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, so pl. 235237 0. (4-Methyl-N-acetylphenylsulfoximely) -butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, so pl. 109110 ° C. 6- 4- (4-Bromo-3-methyl-N-acetylphenylsulfoximino) -butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, so pl. 152-154 ° C, 6- 4- (3,4-Dichloro-N-acetylphenylsulfoximino) -butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, mp 1566-4- (N-Acetylphenylsulphoximino) -butoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one, m.p. 112-114 C. (4-Chloro-M-acetylphenylsulfoximino) -butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, so pl. 120-122 C, 6- 4- (4-Methyl-N-acetylphenylsulphoxymino) -butoxy-4,4-di-n-hexyl-4H-3, 1-benzoxazin-2-one. . , Oil, RF ratio: 0.4 (silica gel plate: chloroform and acetone 9: 1). %: C, 67.78; H 8.27; Calculated S 5.48. (584.82) s, l “, c 67.89; H 8.31; Found, S 5.60. (4-Cyclohexyl-N-acetylphenylsulfoximino) -butoxy-, 4-di-n-hexyl-4H-3, 1-benzoxazin-2-one, mp. 134136 ° C. 6-C4- (3,4-Dichloro-M-acetylphenylsulphoxymino) -butoxy-4,4-di-n-hexyl-4H-3, 1-benzoxazin-2-one. . Oil, RF ratio: 0.54 (silica gel plate, chloroform and acetone 9: 1). / Calculated ,,%: C 60.08; H 6.93; cr 11.08; S 5.01. (639.70) Found,%: C 59.87; H 7.13-, cr 11.20; S 4.95. 6- 4- (4-Acetamido-N-acetylphenylsulfoximino) -butoxy-4,4-di-n-hexyl-4H-3, 1-benzoxazin-2-one, so pl. 122-124 ° C. (4-Acetamido-M-acetylphenylsulfoximino) -butoxy-4,4-dicyclohexyl-4H-3, 1-benzoxazin-2-one. m.p. 146 C (decomposition). 6- 4- (4-Methyl-N-acetylphenylsulfoximino) -butoxy-4, 4-dicyclohexyl-4H-3, 1-bezszsazin-2-one, so pl. 148-149 C. 6- 4 | -Acetamido-N-ace.tilphenylsuximino) -butoxyZ-4H-3,1-benzox ZIN-2-OH, so pl. 200-201 ° C. 6- {4- (4-Methyl-I-acetylphenylsul-ximino) -butoxn-4H-3,1-benzoxazIN-2-OH. Oil, RF ratio: 0.62 (silica gel plate: chloroform 9: 1 ethyl acetate). 6- 4- (4-Cyclohexyl-N-acetylphenylsulphoxymino) -butoxy-4H-3, -benzoxazin-2-one, mp. 124-125 C 6- 4- (4-Cyclohexyl-N-acetylfe sulfoxymino) -butoxy-4,4-dicyclic hexyl-4H-3,1-benzoxazin-2-one, m.p. 130 ° C. 6-C5- (3,4-Dichloro-N-acetylphenyl sulfoxymino) -pentoxy-4,4-dimet-4H-3,1-benzoxazin-2-one, so pl. 12 128 ° C. (4-Cyclohexyl-N-acetyl. P,, phenylsulfoximino) -pentoxy-4.4,4-methyl-4H-3, 1-benzoxazin-2-one, so pl. 95-96 ° C. (4-Cyclohexyl-N-acetylphenylsulfoximino) -propoxyZ-4,4-di TIL-4H-3,1-beneoxazin-2-one, so pl. 114-115С. 6- 3- (3,4-Lichlor-N-acetylphenyl sulfoxymino) -propoxyT-4,4-dimethyl-4H-3, 1-benzoxazine -2-one, t.gsh. 200 ° C. (3,4-Dichloro-N-acetylphenyl sulfoxymino) -ethoxy 3-4,4-dimethyl-3,1-benzoxazin-2-one, mp. 154155 ° C. t g / / o / tti (3,4-Dimethyl-acetylphenium sulfoxymino) -butoxy-4H-3,1-ben oxazin-2-one. Resin, RF ratio: 0.7 (silica gel plate: chloroform 1). ethanol 9,; Calculated by; ; C, 61.38; H 6.09. 6.5f, s 7.45. .OjS Found,%: C 61.79; H 6.32; 6.24; S 7.38. 6- 4- (3,4-Dimethyl-N-acetylphenyl sulfoxymino) -butoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one, so pl. 146 ° C. 6-C4- (3,4-Dichloro-M-acetylphenyl sulfoxymino) -butoxy-4-ETHIL-4H-3, 1-benzoxazin-2-one, mp 156158 ° C. 25DO (3,4-Dichloro-L-acetylphenylsulfoximino) -hexyloxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one. Oil, RF ratio: 0.64 (silica gel plate: chloroform and ethanol 9: 1). C, 54.63; H, 3.35; Calculated,%: 6.08. (327.48) W4, 7 ,: C 54.30, H 5.34, .; Found, S 6.06. 6-b- (3,4-Dimethoxy-Y-acetylenylsulfoximino) -hexyloxy-1-4, 4-dimethyl-4H-3, 1-benzoxazin-2-one, Oil, RF ratio: 0.63 (silica gel plate: chloroform; 1) . ethanol 9 H 6.61,%: C 60.21; Calculated 6.18. (518, ba)., S C 59.90; H Found,%; 6-G4- (3,4-Dichloro-N-p-toluene sulfonylphenylsulfoximino) -butoxy-4, 4-dimethyl-4H-3,1-benzoxazin-2on, m.p. 174-175 ° C. (3,4-Dimethoxy-1-acetylenylsulfoximino) -propoxy-4-isopropyl-4H-3, 1-benzoxazin-2-one,. pl, 73-75C. 6- 4- (3,4-Dimethylphenylsulfoxino) -butoxy-4H-3,1-benzoxazin2-one, m.p. 169-170 ° C. 6- 4- (3,4-Limethylphenylsulfoxino) -butoxy3-4, -dimethyl-4H-3,1 benzoxazin-2-one, so pl. 162-163 C. (3,4-Dichlorophenylsulfoximio) -hexyloxy-4,4-dimethyl-4H-3.1-benzoxazin-2-oi, m.p. 135-136 C. (3,4-Dichlorophenylsulphoxy „-, yno) -butoxy-4-ethyl-4H-3,1-benzok azin-2-one, so pl. 132-133 ° C. (3,4-Dimethoxyphenylsulfosimino) -hexyloxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, m.p. 10809 ° C. 6- 4- (3,4-Dichlorophenylsulfoximio) -butoxy-4-IZOPROPSH1-4H-3,1 benzoxazin-2-one, so pl. 123-125p. 6- 4- (3,4-Dichlorophenylsulfimino) butoxy-4,4-dimethyl-4H-3,1-benzok azin-2-one, so pl. 165-166 ° C. (3,4-Dimethoxiphenylsulfon-imine) -proproxy-4-we-isopropyl-4H-3, 1-benzoxazin-2-one, mp: 12325 ° C. 1-benzoxazin-2-one. Resin, RF ratio: 0.45 (silica gel plate: chloroform and ethanol 9: 1). Calculated,%: C 52.52; H 4.85, S 7.01. C (457.38) Found,%: C 52.49} H 5.12; S 6.63. . The novel compounds of general formula 1 exhibit valuable pharmacological properties, preferably an antithrombotic effect. . They increase the synthesis of inhibitory aggregation of prostaglandins in the vessel wall and also have a inhibitory effect on tumor metastasis. This is due to the following properties of the compounds obtained: platelet phosphodiesterase inhibitors which are known as tumor metastasis inhibitors. The compounds of formula 1 also inhibit primary hemostasis already at very low dosing. The adherence of thromocytes to the damaged vessel and the formation of a white thrombus prevents c, which leads to a significant lengthening of the bleeding time. This is explained not only by the weakening of the function of platelets, but also by the additional increased formation of prostaglandins acting on platelets by the endothelial cell, the vessel. This is confirmed by the fact that the blood flow time does not increase if the synthesis of endothelial cell prostacyclin cells is stopped by premature administration of cyclooxygenase inhibitors. Thus, the compounds of formula 1 are still an unknown, optimal combination of two principles of action. According to Hönn, a certain increase in activity or CI, the prostaglandin- (12) thesis in the vessel wall 1, is also a reason for inhibiting tumor metastasis. Thus, the following compounds of formula 1: A (4-chlorophenylsulfinyl) -byoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one, B (4-Oxyphenylsulfoximino) -butoxy-4,4-dimethyl-4H -3, 1-benzoxazin-2-one, 42 (4-methoxyphenylsulfoximino) -butoxy} -4,4-dimethyl-4H-3, 1-benzoxazin-2-one, (4-methylphenylsulfinyl) -butoxy-4, 4 -dimethyl-4H-3,1-benzoxazin-2-one, (4-cyclohexylphenylsulfinyl) -butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, 6-4- (3,4- dichlorophenylsulfoximino) -butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, 6-GZ-methoxyphenylsulfoxymino) -butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, 6-4- (4-fluorophenylsulfok imino) -butoxy2-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, (4-bromophenylsulfoximino) -butoxy-4,4-dimetsh-4H-3, 1-benzoxazin-2-one, 6 - (4-phenylsulfinylbutoxy) -4H-3, 1-benzoxazin-2-one, 6-4- (4-bromophenylsulfinyl) -butoxy-4,4-dimethyl-4H-3,1-benzoxazin-2-one, 6 - 4- (4-bromo-3-methylphenylsulfoxymino) -butoxy-4,4-dimethyl-4H-3, 1-b nzoxazin-2-one, (4-methyl-phenylsulfoxymino) -butoxy-4,4-dimethyl 4I-3 , 1-benzoxazin-2-one, 6- 4- (3,4-dimethoxy (phenylsulfoximino) -butoxy-4,4-dimethyl-4H-3, 1-benzoxazin-2-one, (4-amino-3, 5-dibromophenylsulfinyl) -butoxy-4,4--. -dimethyl-4H-3,1-bvnsoxazin-2-one, (4-biphenyl-1sulfoximino) -butoxyP-4, 4-dimethyl-4H-3, 1-benzoxazin-2-one, (3,4-dimethoxy-N - acetylphenylsulfoximino) -butox-4,4-dimethyl-4H-3,1-benzoxazIN-2-OH, (3,5-di-tert-butyl-4-hydroxy-N-acetylphenylsulfoximino) -butoxy-4,4-dimethyl4H -3, 1-benzoxazin-2-one, -bromo-4,4-dimethyl-6-4- (4-methylphenylsulfoximino) -butoxy-4H-3,1-benzoxazin-2-it, chloro-4,4-dimethyl- 6- 4- (4-meylphenylsulfinyl) -butoxy 4H-3, 1-benzoxazin-2-one. X 7-bromo-6-A- (3,4-lichlorophenylsulfinyl) -butoxy | -4,4-dimethyl-4H-3, 1-benzoxazin-2-one C (4-biphenylsulfinyl) -butoKCiiJ-4,4-dimet L-4H-3,1 -ben oxazin-2-oi, is tested for their biological properties as follows. 1, Inhibition of phosphodiesterase. CAMP is hydrolyzed from phosphodiesterase from various sources, including platelets, to adenosine-5-phosphoric acid. Hydrolysis is inhibited, depending on the concentration of phosphodiesterase inhibitors. As phosphodiesterase, 10,000 X S-supernatants of humane platelets are used, which are frozen with water and thawed. 0.3 ml of a mixture containing 0.1 mol / l Tris-oxy-aminomethane (pH value 7.4), 3 mmol / l of magnesium chloride, 1 ppm / adenosine-5-fBsporic acid, 1 μmol / l ZN-CAMP (specific activity of about 10 MR / micmole), phosphodiesterase, as well as the test substance or water, are incubated for 15 min at 37 ° C. Incubation is stopped by adding 0.3 ml of zinc sulfate (0.266 mol / l) and 0.5 ml of barium hydroxide (0.226 mol / l), separating the precipitate by centrifugation and determining the remaining unreacted 3N-CAMP. After comparing the initial mixture with the control initial one, the concentration of 50% inhibition is determined (concentration of can CT) of each substance. The compounds of formula 1 are compared for their ability to inhibit phosphodiesterase with the known compounds 1-V: t - (2-pyridylsulfinyl) and -butoxy-3, 4-dihydro-carbostyryl, tl - (2-pyridylsulfonyl) -butoxy-3, 4-dihydro-carbostyri, til - 6- 4-phenylsulfonyl) to-3, 4-dihydro-carbostyryl, IV - 6- (4-cyclohexylsulfinylbuhoxy) -3,4-dihydrocarbyl styryl In 6-4- (2,5-dichlorophenyleulphinyl) -butoxy-3,4-dihydro-carbostyryl, exhibiting a similar effect i. The data of the studies are presented below. Concentrations of substances that cause 50%, - inhibition of phosphodiesterase. The data indicate that the new compounds .. A - C show increased activity in comparison with; known 1, 1-Y, as; their dose, at which 5 reaches 50% inhibition of phosphodiesterase, is less than the corresponding dose of the known compounds 1 - 2. Antithrombotic effect. Platelet aggregation is measured by the Born and Cross method in platelet-rich plasma of healthy test subjects. For the purpose of anticoagulation, the blood is mixed with 3-14% sodium citrate in a volume ratio of 15: 1: 10. Collagen-induced aggregation. The decrease in the optical density of the platelet suspension is photometrically measured and recorded after 20 additives of the aggregating agent. The rate of aggregation is determined from the angle of inclination of the curve. The point of the curve, in which the highest permeability of light exists, serves 25 to determine the optical density. The amount of collagen that is as low as possible is chosen, but in such a way that they get irreversibly passing cry-; zoo reaction. Using the usual commercially available collagen (firms Gormmonhemi, Munich, Germany). Prior to supplying collagen, plasma is incubated with the substance for 10 min at 37 C. From the measured data, the effective concentration is graphically determined (3Kj (referring to a 50% change in optical density corresponding to an inhibition of 40 aggregation. The results are shown below. I ECM, micmol / l Time extension Bleeding substance after 1 h,% 7248 263 241 3. Determination of prolonged bleeding time. To determine the bleeding time, the test substance is applied to mice at a dosage of 10 mg / kg P.O. After 1 h, cut off the end of the tail of each animal with a length of 0.5 mm and drain the blood drained with filter paper for 30 seconds until the bleeding stops. From the number of drops of blood, a measure is obtained for the bleeding time (5 animals per experience). The data below indicate the lengthening of the bleeding time compared to control animals that were not given the substance. A3 Extension of time Bleeding substance after 1 h,% 4. Acute toxicity. The groups were determined in groups (out of 10 animals 5 O 5 30 35 40 2548). After oral dosing with substance A-D, C-X (1,000 mg, observation time 14 days), O from 10 animals died. Due to its pharmacological properties, the novel compounds of the formula L are suitable for the prevention of thromboembolic diseases, for example myocardial infarction, cerebral infarction, so-called transient ischemic episodes, passing vision loss, for the prevention of atherosclerosis and metastasis. A dose of 0.3–4 mg, preferably 0.3–2 mg / kg body weight, 2–4 times a day, is required for a corresponding action. For this, the compounds of general formula 1 are produced in combination with other active ingredients, together with one or more inert carriers and / or diluents, such as corn starch, milk sugar, cane caxaip, microcrystalline cellulose, magnesium stearate, polyvinylpyrrolidone, citric acid, tartaric acid, water, water and ethanol, water and glycerin, water and polyethylene glycol, propylene glycol, cetyl stearyl alcohol, carboxymethylcellulose or fat-containing substances, like hardened fat or suitable for them You can, in the form of tablets, dragees, capsules, powders, suspensions or suppositories. Thus, the method allows to obtain new biologically active derivatives of benzoxazin-2-one, which have antithrombotic action, and that exhibit a higher activity during inhibition of phosphodiesterase, than the known analogues in structure and action. .
权利要求:
Claims (2) [1] METHOD FOR PRODUCING NEW GASOLINE [2] 2-OH in the general form - where A is the radical -S-, -SOp, -S0 £ -, R-Ν-έ- or R-N-SO-, where R is a hydrogen atom, acetyl, benzoyl, p-toluenesulfonyl or methanesulfonyl, D is an unbranched or branched alkylene group with 2-6 carbon atoms; Rj is an alkyl group with 1-3 carbon atoms, unsubstituted or substituted by a phenyl group, or a phenyl group, and these phenyl groups can be substituted by an alkyl group with 1-4 carbon atoms, a halogen atom, an alkoxy group with 1-3 carbon atoms, an oxy group, cyclohexyl or phenyl group; alkyl corpse. pa with 4-8 carbon atoms, • a cycloalkyl group with 3-7 carbon atoms, a phenyl group disubstituted by an alkyl group with 1-4 carbon atoms, an alkoxy group with 1-carbon atoms and / or .. halogen atoms; an oxyphenyl ”or nil-aminophenyl group mono- or disubstituted with an alkyl group with 1-4 carbon atoms, an alkoxy group <with 1-3 carbon atoms and / or halogen atoms, the phenyl substituents being the same or different, the pyridyl th hydroxy group a pyridine or pyrimidine ring unsubstituted or substituted with one or two alkyl groups with 1-3 carbon atoms, triazolyl unsubstituted or substituted with one or two alkyl groups with 1-3 carbon atoms, or 2-benzthiazolyl; R ^ h R ^ - may be the same or different - a hydrogen atom, a phenyl group, an alkyl group with 1-6 carbon atoms or a cycloalkyl group with 3-7 carbon atoms; R ^ is a hydrogen atom or an alkyl group with 1-3 carbon atoms. od) SU sy 1138025 a hydrogen or halogen atom, a nitro or alkyl group with 1-3 carbon atoms; a hydrogen or halogen atom or an alkyl group with 1-3 carbon atoms, characterized in that the oxy compound of general formula 11 Λ r 2 r 3Ai j = o Kb where Rg, R ^, Rj, Rg have the indicated meanings, are reacted with a compound of formula 111 Z-D-A-R, where A, D and R have the indicated meanings ( Z is a nucleophilic substitutable group, such as a halogen atom, p-toluenesulfonyloxy or methanesulfonyloxy group, in a solvent medium, in the presence of an alkaline base or an alcoholate, at a temperature from room temperature to the boiling point of the solvent.
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公开号 | 公开日 DD210453A5|1984-06-13| CS236876B2|1985-05-15| FI79704B|1989-10-31| JPS58203979A|1983-11-28| DE3217012A1|1983-11-10| AT24501T|1987-01-15| ES526724A0|1984-07-01| PL241806A1|1984-08-13| GB8312344D0|1983-06-08| GB2119382B|1985-09-18| KR840004736A|1984-10-24| IL68573A|1986-10-31| ES522104A0|1984-02-01| ES8406453A1|1984-07-01| US4518597A|1985-05-21| CA1204744A|1986-05-20| EP0093922A3|1984-01-25| PT76627B|1986-02-26| NO831599L|1983-11-07| YU95783A|1985-10-31| ES8402585A1|1984-02-01| DK195583A|1983-11-07| DK164860C|1993-01-11| FI831412A0|1983-04-26| DK164860B|1992-08-31| GB2119382A|1983-11-16| AU563453B2|1987-07-09| FI831412L|1983-11-07| ES8406454A1|1984-07-01| PL139119B1|1986-12-31| IE831032L|1983-11-06| IE55481B1|1990-09-26| IL68573D0|1983-09-30| DK195583D0|1983-05-03| AU1426583A|1983-11-10| GR79255B|1984-10-22| DE3368621D1|1987-02-05| FI79704C|1990-02-12| EP0093922A2|1983-11-16| HU194842B|1988-03-28| NO158738B|1988-07-18| ES526723A0|1984-07-01| ZA833190B|1985-01-30| KR900006546B1|1990-09-13| NZ204143A|1986-02-21| EP0093922B1|1986-12-30| YU42854B|1988-12-31| PT76627A|1983-06-01| NO158738C|1988-11-16|
引用文献:
公开号 | 申请日 | 公开日 | 申请人 | 专利标题 US3526621A|1966-08-03|1970-09-01|Farmaceutical Italia Soc|Substituted 3,1-benzoxazin-2-one| US3542774A|1968-07-05|1970-11-24|Warner Lambert Pharmaceutical|3,4-dihydrobenzoxazinones| CH624395A5|1976-01-08|1981-07-31|Ciba Geigy Ag| SU843739A3|1978-02-17|1981-06-30|Карл Томэ Гмбх |Method of preparing carbostyryl or oxyindole derivatives| US4442111A|1981-07-25|1984-04-10|Dr. Karl Thomae Gesellschaft Mit Beschrankter Haftung|Antithrombotic sulfimino and sulfoximino indolinones-2|DE3439281A1|1984-10-26|1986-04-30|Bayer Ag, 5090 Leverkusen|CHROMOGENIC 4,4-DIARYL-2-OXO-BENZO-3,1-OXAZINE, THEIR PRODUCTION AND USE| US5663169A|1992-08-07|1997-09-02|Merck & Co., Inc.|Benzoxazinones as inhibitors of HIV reverse transcriptase| IL106507A|1992-08-07|1997-11-20|Merck & Co Inc|Pharmaceutical compositions containing benzoxazinones and some novel compounds of this type| US5874430A|1996-10-02|1999-02-23|Dupont Pharmaceuticals Company|4,4-disubstitued-1,4-dihydro-2H-3,1-benzoxazin-2-ones useful as HIV reverse transcriptase inhibitors and intermediates and processes for making the same| US5965729A|1997-02-05|1999-10-12|Merck & Co., Inc.|Process for the crystallization of a reverse transcriptase inhibitor using an anti-solvent| US6436929B1|1999-05-04|2002-08-20|Wyeth|Cyclothiocarbamate derivatives as progesterone receptor modulators| US6509334B1|1999-05-04|2003-01-21|American Home Products Corporation|Cyclocarbamate derivatives as progesterone receptor modulators| JP5529757B2|2008-01-17|2014-06-25|バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング|Sulfoximine-substituted quinazoline derivatives as immunomodulators, their preparation and use as pharmaceuticals| EP3102567B1|2014-02-04|2019-07-17|University of Tennessee Research Foundation|Inhibitors of paxillin function and related compositions and methods|
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申请号 | 申请日 | 专利标题 DE19823217012|DE3217012A1|1982-05-06|1982-05-06|BENZOXAZIN-2-ONE, THEIR PRODUCTION AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS| 相关专利
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