SU196800A1 - Method of producing 2,4,6-trichlorophenyl esters of alkyl or cycloalkylcarbamic acids - Google Patents
Method of producing 2,4,6-trichlorophenyl esters of alkyl or cycloalkylcarbamic acidsInfo
- Publication number
- SU196800A1 SU196800A1 SU941838A SU941838A SU196800A1 SU 196800 A1 SU196800 A1 SU 196800A1 SU 941838 A SU941838 A SU 941838A SU 941838 A SU941838 A SU 941838A SU 196800 A1 SU196800 A1 SU 196800A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- alkyl
- trichlorophenyl
- acids
- producing
- cycloalkylcarbamic
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 6
- 125000000217 alkyl group Chemical group 0.000 title claims description 3
- -1 2,4,6-trichlorophenyl esters Chemical class 0.000 title description 6
- 150000007513 acids Chemical class 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- UPFQVVDUHJVSON-UHFFFAOYSA-N 1,3,5-trichloro-2-(2,4,6-trichlorophenoxy)benzene Chemical class ClC1=CC(Cl)=CC(Cl)=C1OC1=C(Cl)C=C(Cl)C=C1Cl UPFQVVDUHJVSON-UHFFFAOYSA-N 0.000 claims description 4
- 230000000855 fungicidal Effects 0.000 claims description 3
- 239000000417 fungicide Substances 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- LINPIYWFGCPVIE-UHFFFAOYSA-N 2,4,6-Trichlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1Cl LINPIYWFGCPVIE-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229940086542 triethylamine Drugs 0.000 description 2
- PFDJIMKTGBPMEC-UHFFFAOYSA-N 2-methylpropylcarbamic acid Chemical compound CC(C)CNC(O)=O PFDJIMKTGBPMEC-UHFFFAOYSA-N 0.000 description 1
- KDSNLYIMUZNERS-UHFFFAOYSA-N Isobutylamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QCIGLPLDNRDLQQ-UHFFFAOYSA-N butan-2-ylcarbamic acid Chemical class CCC(C)NC(O)=O QCIGLPLDNRDLQQ-UHFFFAOYSA-N 0.000 description 1
- 150000001715 carbamic acids Chemical class 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 1
- RICIHZRFINKXFB-UHFFFAOYSA-N carbonyl dichloride;phenol Chemical compound ClC(Cl)=O.OC1=CC=CC=C1 RICIHZRFINKXFB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000002363 herbicidal Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000000749 insecticidal Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N precursor Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Description
К насто щему времени получено большое число алкил-, алкокси-, ацилфениловых и а-иафтиловых эфиров метилкарбаминовой кислоты, в том числе р д инсектицидов, примен ющихс на практике. Получены охлорфениловыеэфиры N-изопропил- и N-вторбутилкарбаминовых кислот, которые могут быть применены в качестве противоовсюговых гербицидов.To date, a large number of alkyl, alkoxy, acylphenyl and a-butyl methyl esters of methylcarbamic acid have been obtained, including a number of insecticides used in practice. O-chlorophenyl esters of N-isopropyl- and N-sec-butylcarbamic acids have been obtained, which can be used as anti-herbicide herbicides.
Предложен способ получени 2,4,6-трихлорфениловых зфиров алкил- и циклоалкилкарбаминовых кислот, неописанных в литературе, взаимодействием2,4,6-трихлорфениловогоA method has been proposed for the preparation of 2,4,6-trichlorophenyl zofir of alkyl- and cycloalkyl-carbamic acids, not described in the literature, by the interaction of 2,4,6-trichlorophenyl
эфира хлоругольной кислоты (хлоркарбоната ) с алкил- или циклоалкиламинами в среде органического растворител или в воде в присутствии избытка исходного амина или эквивалентного количества другого органического или неорганического основани . Исходный 2, 4,6-трихлорфениловый эфир хлоругольной кислоты, также неописанный в литературе, получают взаимодействием эквимолекул рных количеств фосгена и 2,4,6-трихлорфенола в присутствии триэтил амина в органическом растворителе.chloroic acid ester (chlorocarbonate) with alkyl- or cycloalkylamines in the medium of an organic solvent or in water in the presence of an excess of the starting amine or an equivalent amount of another organic or inorganic base. Chloroic acid precursor 2, 4,6-trichlorophenyl ester, also not described in the literature, is obtained by the interaction of equimolecular amounts of phosgene and 2,4,6-trichlorophenol in the presence of triethyl amine in an organic solvent.
Синтезированные 2,4,6-трихлорфениловые эфиры алкил- и циклоалкилкарбаминовых кислот по своей фунгицидпой активности в несколько раз превосход т широко примен емый в качестве фунгицида препарат фигой.The synthesized 2,4,6-trichlorophenyl ethers of alkyl- and cycloalkyl-carbamic acids are in their fungicide activity several times superior to the preparation widely used as a fungicide.
Пример. К смеси 70 г 2,4,6-трихлорфенола и 42 г фосгена в 300 мл сухого толуола при температуре смеси от -10 до 8°С и энергичном перемешивании прибавл ют 47 г триэтиламина . Смесь перемешивают при 20°С еще 1 час, выделившийс сол нокислый триэтнламин отфильтровывают, осадок на фильтре промывают толуолом, фильтраты объедин ют , охлаждают до 0°С, промывают разбавленпой сол ной кислотой, а затем лед ной водой до нейтральной реакции. После промывкп раствор сушат над сернокислым магнием, отгон ют растворитель в вакууме водоструйного насоса, а остаток перегон ют в высоком вакууме, получа 89 г (96,6Vo от теории) 2,4,6-трнхлорфенилового эфира хлоругольной кислоты с т. кип. 94-100°С (0,2 мм рг. ст.),Example. To a mixture of 70 g of 2,4,6-trichlorophenol and 42 g of phosgene in 300 ml of dry toluene at a temperature of the mixture from -10 to 8 ° C and vigorous stirring was added 47 g of triethylamine. The mixture is stirred at 20 ° C for another 1 hour, the triethnlamine hydrochloride is filtered off, the filter cake is washed with toluene, the filtrates are combined, cooled to 0 ° C, washed with dilute hydrochloric acid, and then with ice water until neutral. After washing, the solution is dried over magnesium sulphate, the solvent is distilled off in a water jet pump vacuum, and the residue is distilled under high vacuum to obtain 89 g (96.6Vo from theory) of chlorofactoric acid 2,4,6-trhlorophenyl ester with m.p. 94-100 ° C (0.2 mm or rg. Art.),
9999
По 1,5478.At 1.5478.
К раствору 6,31 г изобутиламина в 150 мл воды при перемешивании и температуре смеси от О до -4°С прибавл ют 10 г 2,4,6-трихлорфенилового эфира хлоругольной кислоты. По окончании внесени эфира охлаждение снимают и перемешивание смеси продолжают еш,е в течение 2 ч.ас при 15-20°С. Выпавший в виде осадка 2,4,6-трихлорфениловый эфир N-изобутилкарбаминовой кислоты отфильтровыпают , промывают водой и высушивают вTo a solution of 6.31 g of isobutylamine in 150 ml of water with stirring and the temperature of the mixture from 0 to -4 ° C, add 10 g of chlorogolic acid 2,4,6-trichlorophenyl ester. At the end of the ether addition, the cooling is removed and the mixture is stirred for an additional e, e for 2 hours at 15–20 ° C. The 2,4,6-trichlorophenyl ester of N-isobutylcarbamic acid precipitated as a precipitate is filtered off, washed with water and dried in
вакууме. Выход 10,3 г (ЭОо/о от теории), т. пл. 124-125°С (из петролейного эфира).vacuum. Yield 10.3 g (EOo / o from theory), so pl. 124-125 ° C (from petroleum ether).
В таблице приведены свойства 2,4,6-трихлорфениловых эфиров, карбаминовых кислот общей формулыThe table shows the properties of 2,4,6-trichlorphenyl ethers, carbamic acids of the general formula
CiCi
С1 - f -OCONHR -С1C1 - f -OCONHR -C1
Предмет изобретени Subject invention
Claims (2)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU196800A1 true SU196800A1 (en) |
Family
ID=
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2614300A1 (en) * | 1987-04-22 | 1988-10-28 | Sanofi Sa | NEW PROCESS FOR OBTAINING ACTIVE CARBAMATES |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2614300A1 (en) * | 1987-04-22 | 1988-10-28 | Sanofi Sa | NEW PROCESS FOR OBTAINING ACTIVE CARBAMATES |
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