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    1506090 Sulphenamide derivatives UNION CARBIDE CORP 30 Nov 1976 [1 Dec 1975] 49811/76 Heading C2 Novel sulphenamide derivatives of the formula wherein R and R<SP>1</SP> are C 1-4 alky] groups and R<SP>11</SP> is an optionally substituted alkyl, cycloalkyl, phenylalkyl, naphthylalkyl, or heterocyclylalkyl group, the substituents being selected from halogen atoms and cyano, nitro, alkyl, alkylthio, alkoxy, alkylsulphinyl, alkylsulphonyl, alkoxycarbonyloxylamino, or alkylcarbonylamino groups or R<SP>11</SP> is an alkoxyalkyleneoxyalkyl, alkoxy (dialkyleneoxy) alkyl or alkoxy (trialkyleneoxy) alkyl group, provided that except when R<SP>11</SP> is an alkyl group, no single alkyl or alkylene group in R<SP>11</SP> may contain more than six carbon atoms, are obtained (1) by reacting thio bis carbamoyl fluorides, with hydroxy compounds HOR<SP>11</SP>, or (2) by reacting fluroformic amides FCONHR with chlorosulphenyl compounds Cl-S-NR<SP>1</SP>-COOR<SP>11</SP>. The chlorosulphenyl compounds of the formula Cl-S-NR<SP>1</SP>-COOR<SP>11</SP> may be obtained by reacting sulphur dioxide with appropriate carbamates.
    公开号:SU886737A3
    申请号:SU762424152
    申请日:1976-11-30
    公开日:1981-11-30
    发明作者:Чуанг Лианг Вью
    申请人:Юнион Карбид Корпорейшн (Фирма)；
    IPC主号:
    专利说明:

    (54) METHOD FOR PRODUCING CARBAMOIL FLUORIDE The invention relates to the synthesis of new organic compounds, specifically carbamoyl fluorides of the general formula. C T - cJo-isr- -i - ((I where R and R have the same or different meanings and mean alkyl Q, -C "R - alkyl, which may be substituted by a benzyl alkoxy group. New compounds of general formula 1 may be are applicable as intermediate products in the preparation of pesticide formulations by reacting with oximes, for example 2-ox-imino-1,4-dithian. The purpose of the invention is to produce new, useful compounds with which pesticidal compositions can be obtained. connection with the release of hydrogen halide pJ. The goal is achieved by the method of obtaining carb, amoyl fluoride of general formula T by reacting carbamoyl fluoride of general formula F-CO-NH-R, GT) where R has the above values, with a compound of the general formula Ce-SN-CO-OR X where; R and R have the above meanings, in an inert solvent medium at 0–5 ° C in the presence of an acid binder. This reaction should be carried out in the presence of at least one equivalent of an acid binding agent, which may be an organic or inorganic about Considerations such as triethylamine, diazaditsiklooktan, pyridine, or sodium or potassium hydroxide. . Generally, the reaction should be carried out in the presence of an inert solvent, for example ether, a chlorinated hydrocarbon or an aromatic solvent, or any of the many inert organic solvents commonly used in such reactions. Examples of inert solvents that may be used are methylene chloride, chloroform, dioxane, tetrahydrofuran, benzene, toluene, acetone, dimethoxyethane, dimethylformamide, acetonitrile, and the like. The temperature is not critical when conducting these reactions and is in the range of from about -50 to about. Preferably, these reactions should be carried out in a temperature range from about O to. The starting compound, carbamoyl fluoride of the general formula C, is obtained by a known chemical reaction by the interaction of hydrogen fluoride and alkyl aldioate. The data of the proton nuclear magnetic resonance spectrum prove unambiguously the formation of this product 2. Therefore, carbamoyl fluoride does not isolate the reaction mass. Example 1. Preparation of M- / N-ethoxycarbonyl-K-methylaminosulfenyl / -H-methylcarbamoyl fluoride. To a solution of 72 g (0.7 mol) of sulfuric chloride in 200 ml of methylene chloride, cooled to 0 ° C, a mixture of 51 g (0.5 mol) of N-methylethylcarbamate and 51.0 g (51 0.5 mol of triethylamine in 100 ml of methylene chloride, keeping the temperature between -4 and 5 ° C. After stirring for 1 hour, the mixture is filtered and the filtrate is evaporated. From the residue containing a small amount of amine salt, the organic product is extracted with hexane. After filtration and evaporation, 94 g of an amber oil are obtained. In a polyethylene reactor equipped with a stainless steel stirrer with a blind channel for. anhydrous hydrogen fluoride {South, 0.3 mol) and 600 ml of methylene chloride at a temperature of 0 ° C are added with a thermocouple and dry ice polyethylene condenser. Then methyl isocyanate (28.5 g, 0.5 mol) is added dropwise, maintaining the temperature in range from -6 to 0 ° /. After stirring for 1 hour at G-5 ° C, the solution prepared above is added in the manner described above to a solution of 94 g of N-chlorothiocarbamate and then 51.0 g (0.5 mol) of triethylamine is added dropwise. The mixture is warmed to room temperature and water is added. After extensive mixing the layer is separated. The lower organic layer is washed with a saturated aqueous solution of sodium bicarbonate and then with water until neutral reaction to litmus, dried over anhydrous magnesium sulphate, filtered and evaporated, to give 97.0 g (92%) of an oily residue. ka After distillation under reduced pressure, 68.4 g of N- / N-ethoxy carbonyl-S-methylaminosulphenyl / -M-methylcarbamoyl fluoride are obtained, b.p. 77 ° C / / 0,24 mm. % H, DAZ Composition Calculated,%: C 34.28 .; H 5.28; N13.33. Found,%: C 34.05; And 5.13; N13,10., Example 2. Getting f | / - / N-H-butoxycarbonyl-N-methylaminosulfonyl / -M-methylcarbamoyl fluoride. To a solution of 45.2 g (0.44 mol) of sulfur dichloride in 200 ml of methylene chloride, cooled, valuable before, before. . Add the solution under nitrogen atmosphere, compare with 50.9 g (0.5 Mole n-butyl M methylcarbamate, 44.5 g (0.44 mol) triethylamine 100 ml methylene chloride. Addition is continued for 24 hours at a temperature of After stirring for 1 h, cNfecb is filtered under a positive nitrogen pressure and the filtrate is evaporated. The solid is separated by extraction with hexanes. After filtering, the hexane solution is evaporated and 57.3 g of n-butyl-N-chloro-thio 1-methane carbamate is obtained. In a polyethylene reactor, anhydrous hydrogen fluoride (8 g, 0.4 mol) is added to 400 ml of methylene chloride. at -5 to methyl isocyanate (22.8 g, 0.4 mol). After stirring for 1 hour, a solution of 57.3 g and -butyl is added to the reaction mixture. -Kb-chlorothio-M-methylcarbamate in 100 ml of methylene chloride, then 40.5 g (0.4 mol) of triethylamine are added dropwise. After warming to room temperature, 300 ml of water are added with vigorous stirring. The lower organic layer is washed with a saturated sodium bicarbonate solution, then with water to obtain a neutral industrial water NJL, dried over anhydrous sulfate is magnesium fil ruyut and evaporated to yield 57.6 g of an oily residue. After distillation under reduced pressure, 32.1 g of N- / N-n-butoxycarbonyl-N-methlaminosulfenyl / -N-methylcarbamoyl fluoride are obtained, b.p. 92C / / 0.30 mm. Composition Calculated,%: C 40.33; H 6.35; N 11.76. Found,%: C 39.23; H 6.46; MP, 23. Example 3. Obtaining N - / 1 -tert-butoxycarbonyl-N-methylaminosulfonyl / - l-methylcarbamoylptoid. To a solution of 62 g (0.6 mol) of sulfur dichloride in 200 ml of methylene chloride, cooled to, a solution consisting of 50.9 g (0.4 mol) of tert-butyl-1 | -methylcarbamate is added to the atmosphere of nitrogen. , 44.5 g (0.44 mol) of three ethylamine and) 00 ml of methylene chloride. When added, the temperature is maintained in the range from -2 to. After stirring for another 1 h at 5 ° C, the mixture is filtered under positive nitrogen pressure and the filtrate is evaporated. The solid is separated by hexane extrusion. After filtration, the hexane solution is evaporated and 81.5 g of tert-butyl-M-chlorothio-Mm of tilcarbamate are obtained. In a polyethylene reactor, anhydrous hydrogen fluoride (8 g, 0.4 mol) is added to 400 ml of methylene chloride. It is then added over a period of 0.5 hours at a temperature of from -10 to. O C methyl isocyanate (22.8 g, 0.4 mol). After stirring for 1 hour, a solution of 81.6 g of tert-butyl-M-chlorothio-M-methylcarbamate in 100 ml of methylene chloride is added to the reaction mixture, then 40.5 g (0.4 mol) of tristilamine are added dropwise . The mixture is heated to room temperature. Water (300 ml) is added with vigorous stirring. The lower organic layer is washed with a saturated sodium bicarbonate solution, then with water until neutral wash water, dried over anhydrous magnesium sulphate, filtered, evaporated to give 86.9 g of an oily residue. After distillation under reduced pressure, 63 g of N - / L1- are obtained. tert-butoxycarbonyl-M-methylaminosulfenyl / -W-methylcarbamoyl fluoride, b.p. , 25 mm. Composition CgH.p.FN2Oe, 9 Calculated,%: C 40.33; H 6.35; N11.76. Found X: C 40.04; H 6.49; N11.42. PRI me R 4. Obtaining N - / N-2-methoxyethoxycarbonyl-N-methylaminosulfenyl / H-methylcarbamoylfluoride. To a solution of 72 g (0.7 mol) of sulfur dichloride in 200 ml of methylene chloride, cooled before, in a nitrogen atmosphere, a solution consisting of 66.6 g (0.5 mol) of 2-methoxy-ethoxy-methyl carbamate, 55.7 g (0.55 mol) of triethyl nna and 100 ml of methylene chloride. The addition is continued for 2.5 hours at a temperature of from -U to 4 ° C. After stirring for another 1 hour at fP C, the mixture is filtered under a positive nitrogen pressure and the filtrate is evaporated. The solid is separated by extracting the liquid product with 300 ml of hexane. After filtration, the hexane solution is evaporated to give 106.52 g of 2-methoxy-ethyl chlorothio-M-methyl carbamate. In a polyethylene reactor, anhydrous hydrogen fluoride (10.0 g, 0.5 mol) is added at 400 ° C to 400 ml of methylene chloride. Then at -10 to methyl isocyanate (28.6 g, O, 5 mol) is added over 0.5 h. After stirring for an hour, a solution of 106.5 g of 2- -methoxyethyl-N-chlorothio-C methylcarbamate in 100 ml of methylene chloride is added to the reaction mixture, then 50.7 g (0.5 mol) of triethylamine are added dropwise. The mixture is stirred at, for more; 1 hour. After heating to ambient temperature, 300 ml of water are added and the mixture is vigorously stirred. The organic layer is washed with a saturated aqueous solution of sodium bicarbonate, then with water until neutral wash water is obtained, dried over anhydrous magnesium sulfate, filtered, evaporated to give 111 g of an oily residue. After distillation under reduced pressure, 74 g (B1%) of H- / M-2-methoxyethoxycarbonyl-N-methylaminosulfenyl-W-methylcarbamoyl fluoride are obtained, mp. 107C / 0.43 mm. Composition b Calculated,%:, 97; H 5.45; Hi 1.66. C 34.82; H 5.54; Found 11.40. Example 5. Preparation of IN- / Nn-dodecyloxycarbonyl-M-methylamino-sulphenyl / -1 (| -methylcarbamoyl fluoride. To a solution of 62 g (0.6 mol) of sulfur dichloride in 200 ml of methylene chloride, cooled to, is added in an atmosphere nitrogen solution consisting of 97.4 g (.0.4 mol) of n-dodecylmethyl carbamate, 44.5 g (0.44 mol) of triethylamine and 150 ml of methylene chloride. The addition lasts 2.3 hours at a temperature of from -10 to After stirring for an additional 1 hour, the mixture is filtered under a positive nitrogen pressure and the filtrate is burnt; hydrochloric triethylamine is separated by extraction 200 ml of hexane. After filtration, the hexane solution is evaporated and 125.6 g of n-dodedyl-W-chlorothio-M-methyl metal are obtained. In the ethylene reactor, anhydrous hydrogen fluoride (8 g, 0.4 mol) is added at about C to 400, Mji methylene chloride. Then, within 0.5 hours, methyl isocyanate {22.8 g, 0.4 fashion) is added at -5 to ORS. After stirring for 1 h at a temperature, a solution of 25.6 g of n-dodecyl-chloro-S) -silcarbamate in 100 ml of matenylene chloride is added, then in °. 40.5 g (.0.4 mol of triethylamine) are added dropwise. The mixture is stirred at 0 ° C for 1 hour and allowed to warm to ambient temperature. Water (30 ml) is added with vigorous stirring. The organic layer is washed with valuable water) with 1M sodium bicarbonate solution, then with water to obtain neutral pro-wash water, dried over anhydrous magnesium sulphate, filtered, evaporated to obtain 129 g (92%) of oily N- / -nododecyloxycarbonyl-N-methyl aminosulfenyl / - -methylcarbamoyl fluoride. Composition C. Calculated,%: C 54,8J; H 8.92; N 7.99. Found,%: C 55.17; H 9.09; N7.40. Example 6. Preparation of N- / N-2-ethylhexyloxycarbonyl-M-mutemine Laminophenol / -N-methylcarbamoyl fluoride. A solution of 75 g (0.4 ml) of 2-ethylhexyl-M-methyl carbamate and 44.5 g (0, 44 moles of triethylamine in 100 ml of methylene chloride at a temperature of from -10 to C. The addition lasts 2 hours. After stirring for 1 h at 5 ° C, the mixture is filtered under a positive nitrogen pressure and the filtrate is evaporated. The product is extracted with 200 ml of hexane and solid triethylamine is filtered. rat is evaporated and 105.4 g2-ethylhexyl-β-sslortio-M-methylcarbam is obtained. In a polyethylene reactor, anhydrous hydrogen fluoride (8 g, 0.4 mol) is added to 400 ml of methylene chloride .. Then for 0, .5iT and boil at a temperature from -10 to methyl isocyanate (22.8 g, 0, 4 mol.) After 1 hour of stirring, a solution of 105.4 g of 2-ethylhexyl-M-chlorothio-N-methyl sharbamate in 100 ml of methylene chloride is added to the OS and then 40.5 g (0.4 mol) of triethylayin are added dropwise The mixture is stirred for 1 h and heated to ambient temperature. Add that water (300 ml) Yri to vigorous stirring. The organic layer is washed with a single sodium bicarbonate solution and then with water to obtain neural gels, dried over anhydrous magnesium sulfate, filtered, evaporated, and obtain 110 g of oily residues. After distillation under reduced pressure, 77 g (65%) of N- / N g-ethylhexyloxycarbonyl | ) -methylaminosulfenyl / -M-methylcarbamoyl fluoride, bp. 130C / 0.5 mm. Composition (2b 2.0 3 S Calculated,%: C 48.96; H 7.87; H9.51. Found%: C 49.42; H 7.60; N9.34. P p and measure 7 Getting M - / N -benyl sicarb onyl-N-methylaminosulfenyl / -N-methylcarbamoyl fluoride ... - 9 To a solution of 46.3 g (mol) of sulfur dichloride in 200 yl of methylene chloride, cooled to 0 ° C, add in a nitrogen atmosphere a solution of 49.6 g (0.3 mol) beisyl-M-methylcarbam (ata and 33.4 g C 0.33 mol) of triethylamine in 100 ml of methylene chloride at a temperature of from -6 to 5 C for 2.3 hours. The mixture is stirred for another 1 h at and then filtered under a positive pressure of nitrogen. The filtrate is evaporated. The product is cinge 200 ml of hexane and separated by filtration from triethylamine hydrochloride. The filtrate is evaporated to give 73 g of oil. In anhydrous hydrogen fluoride (6 g, 0.3 mol) to 400 ml of netylene chloride in a polyethylene reactor. Then within 0.5 at -6 to oC methyl isocyanate (g, 0.3 mol.) After stirring for 1 hour, a solution of 73 g of the obtained crude oil in 100 ml of methylene chloride is added, and then 23.3 g are added dropwise (0.23 mol) of triethylanin. The mixture is stirred for 1 h at and heated to ambient temperature. Water is added, np) with vigorous stirring. The organic layer is washed with an aqueous solution of sodium bicarbonate, then water is dried over anhydrous magnesium sulphate and filtered, and the residue is evaporated to give 73 g of residue. After pedegojki under reduced pressure get 34 g of 42%) N- / N-benzyloxycarboish-N Methylaminosulphenyl / -M-mets1karbamoshg fluoride, so kip. 55 mm. Composition C H., FN2Oo, 9 Calculated,%: C 48.52; H 4.81; N10.29. Found,%: C 48.41; H 4.87; N10.12. EXAMPLE 8 Preparation of (2-methoxyethoxy) ethoxycarbonyl 3-M-methylaminosulfenyl-N-methylcarbamoyl fluoride. To a solution of 46.3 g of 10.45 mol) sulfuric chloride in 200 ml of methylene chloride, cooled to, a solution of 53.2 g is added under nitrogen atmosphere. (0.3 mol) N-methyl-2- (2-mutoxyegoxy) ethylcarbamate and 33.4 g (0.33 mol) of triethylamine in 100 ml of methylene chloride at a temperature of -2 to 4 C for 2.3 hours The mixture is stirred for another 1 h at, then filtered under a positive nitrogen pressure. After evaporation of the filtrate, 200 ml of hexane was added to extract the product. The triethylamine hydrochloride is filtered off, the filtrate is evaporated and an oily product is obtained. In a polyethylene reactor, add anhydrous hydrogen fluoride (6.0 G, 0.3 mol) to 400 ml of methylene chloride. Then, over a period of 0.5 h, at -7 to methyl isocyanate (17.1 g, 0.3, mol) is added. After stirring for 1 hour at 0 ° C, a solution of the oily intermediate product obtained above in 100 ml of methylene chloride is added, then 30.4 g (0.3 triethylamine) is added dropwise. The mixture is stirred at 0 ° C for 1 hour and heated to ambient temperature. Water (300 ml) is added with vigorous stirring. The aqueous layer is saturated with sodium chloride and the organic layer is separated with sodium bicarbonate aqueous solution, then twice with saturated sodium chloride solution, dried over anhydrous magnesium sulphate, filter are evaporated and 77 g (.90%) of oily N - N-12- (2-methoxyethoxy. oxy) ethoxycarbonyl-3-K} -methylaminosulphenyl-N-methylcarbamoyl fluoride are obtained. Composition CH., PN205S 02; H 6.03; N9.85. Found: C 37.59; H 6.166 N8.96. Example 9. Preparation of W-tN- (l-methyl-2-methoxyethoxycarbonyl) -N-methylaminosulphenyl - -metshtcarbamoyl-FIDE. To a solution of 61.7 g (0.6 mol) of two-sulfuric sulfur in 200 ml of methylene chloride, cooled to 0 ° C, a solution of 58.9 g (0.4 mol) of N-methyl- 1-methyl-2-methoxyethylcarbamate and 44.5 g (0.44 mol) of triethylamine in 100 ml of methylene chloride at temperatures e from -8 to OC for 2 hours. The mixture is stirred for 1 hour at and then filtered under a positive nitrogen pressure. After evaporation of the filtrate, 200 ml of hexane was added to extract the product. The hydrochloric triethylamine is filtered off, the filtrate is evaporated and 90 g of an oily intermediate are obtained. In a polyethylene reactor, anhydrous hydrogen fluoride (8 g, 0.4 mol) is added to 400 ml of methylene chloride. Methyl isocyanane (22.8 g, O, 4 mol) is then added at 0.5 to OC over a period of 0.5 h. After stirring for 1 hour, a solution of 90 g of topical oily intermediate in 100 ml of methylene chloride is added, then II.58 40.5 g (0.4 mol) of triethylamine are added dropwise. The mixture is stirred for 1 hour at and allowed to warm to ambient temperature. Water (300 ml) is added with vigorous stirring. The aqueous layer is saturated with sodium chloride and the organic layer is washed with a saturated aqueous solution of sodium bicarbonate, then with a saturated solution of sodium chloride until neutral, dried over anhydrous magnesium sulphate, filtered, evaporated to give 95 g of residue. After distillation; under reduced pressure, 65.4 g (l-methyl 2-methoxyethioxybranyl) -N-methyl-aminocyanophenyl-1 -N-m to apb amoyl fluoride are obtained, t, kip, 2 mm, Composition CgH 5FN2045 Calculated: C 37.79; H 5.95; N And, 02. . ,
    Comparative biological activity
    R ,, - 0-C N -a-N - C-OR2
     s "qH ,, o 7, Found,%: C 37.60; H 6.00; N110.76, The table presents the results of a series of comparative experiments to demonstrate the advantages of insecticidal and miticidal compounds. luenix 1X of the compounds of the invention, compared with soy-. Dyneniums obtained from other known intermediate compositions of Sz1. "Resultants of this test are expressed in LDcrtiTpe, in parts per million of the test compound required to achieve 50% mortality. The mammalian toxicity is expressed in milligrams of the compound per kilogram of body weight of the rat, required to achieve 50% rat mortality.
    权利要求:
    Claims (3)
    [1]
    l p to M e h a H and e. 1 - means inactivity. Formula of the invention. A method of producing carbamoyl fluoride of the general formula:. -. ZRg-CJO-lSr-0-A-iO OB where R and have the same or Hbie meaning and mean alkyl (L-C; R is alkyl Cj, -C, which can be substituted by alkoxyg. Group - means that benzyl was carried out, which is similar to the fact that carbamoyl fluoride of total forked P. j-eo-1tn - where -R has the above values, is reacted with a compound of the general formula W V ce-sN-co-oRi where R and R have the above indications 1e value, in an inert solvent medium at a temperature of .X -5 ° C in the presence of an acid binder.
    1388673714
    Information sources,
    [2]
    2. George A. Olah, lACS 1973, 14,
    taken into consideration at examination7672-7679. . 1. USSR author's certificate
    [3]
    3. Fahmias and others. I.Agr. Food.
     302336, class C 07 C 125/04, 1968. Chem, 1974, V. 22, p. 59.
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    同族专利:
    公开号 | 公开日
    SE7613427L|1977-06-02|
    GB1506090A|1978-04-05|
    AU503185B2|1979-08-23|
    AU2005876A|1978-06-08|
    NL7613325A|1977-06-03|
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    DK537876A|1977-06-02|
    ATA885076A|1979-06-15|
    BR7607996A|1977-11-08|
    FR2333790A1|1977-07-01|
    IL51002A|1982-09-30|
    IL51002D0|1977-01-31|
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US3812174A|1970-07-14|1974-05-21|Chevron Res|Substituted aryl carbamates|
    DE2254359A1|1972-11-07|1974-05-16|Bayer Ag|N-SULFENYLATED CARBAMATES, THE PROCESS FOR THEIR MANUFACTURING AND THEIR USE AS INSECTICIDES AND ACARICIDES|
    DE2530439C2|1974-07-11|1983-03-03|CIBA-GEIGY AG, 4002 Basel|Bis- [0- -N-methyl-carbamic acid] -N, N'-sulfides, processes for their preparation and pesticides containing these compounds|US4234580A|1977-03-28|1980-11-18|Union Carbide Corporation|Carbamate thiosulfenylcarbamoyl fluoride compounds|
    US4268520A|1978-04-24|1981-05-19|E. I. Du Pont De Nemours And Company|Insecticidal and nematicidal carbamates|
    US4225615A|1978-04-24|1980-09-30|E. I. Du Pont De Nemours And Company|Insecticidal and nematicidal carbamates|
    US4127605A|1978-04-24|1978-11-28|E. I. Du Pont De Nemours And Company|Substituted carbamate intermediate|
    DE3041725C2|1980-11-05|1984-11-29|Standard Elektrik Lorenz Ag, 7000 Stuttgart|Frame of the vertical construction|
    JP4663233B2|2001-11-09|2011-04-06|エンゾン，インコーポレーテッド|Polymeric thiol-linked prodrugs utilizing benzyl elimination systems|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    US05/636,371|US4479002A|1975-12-01|1975-12-01|Carbamate-carbamoyl fluoride compounds|
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