SU528875A3 - Способ получени производных 1,2,3тиадиазола - Google Patents
Способ получени производных 1,2,3тиадиазолаInfo
- Publication number
- SU528875A3 SU528875A3 SU1959282A SU1959282A SU528875A3 SU 528875 A3 SU528875 A3 SU 528875A3 SU 1959282 A SU1959282 A SU 1959282A SU 1959282 A SU1959282 A SU 1959282A SU 528875 A3 SU528875 A3 SU 528875A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mol
- thiadiazole
- producing
- thiadiazole derivatives
- washed
- Prior art date
Links
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical class C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000002474 experimental method Methods 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- PVGHNTXQMCYYGF-UHFFFAOYSA-N thiadiazol-5-amine Chemical compound NC1=CN=NS1 PVGHNTXQMCYYGF-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 description 1
- CPPGZWWUPFWALU-UHFFFAOYSA-N 1-isocyanato-3-methylbenzene Chemical compound CC1=CC=CC(N=C=O)=C1 CPPGZWWUPFWALU-UHFFFAOYSA-N 0.000 description 1
- MFUVCHZWGSJKEQ-UHFFFAOYSA-N 3,4-dichlorphenylisocyanate Chemical compound ClC1=CC=C(N=C=O)C=C1Cl MFUVCHZWGSJKEQ-UHFFFAOYSA-N 0.000 description 1
- MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Смешивают 0,1 мол 5-амино-1,2,3-тиадиазола и 0,1 мол циклогексилизоцианата в 75 мл тетрагидрофурана, добавл ют 0,1 мол триэтиламина в качестве катализатора. После сто ни в течение ночн смесь кип т т 7 час с обратным холодильником. Растворитель отгон ют в вакууме, остаток промывают бензолом , кристаллы отсасывают и еще раз промывают бензолом. Точка текучести 215°С (с разложением ), выход 38,3% от теоретического.
C9Hi4N4OS. Молекул рный вес 225,30.
Найдено, %: 48,54 С; 6,85 Н; 24,вО N.
Пример 4. Получение 5-(Ы-3-хлорфенилкарбамоиламино )-1,2,3-тиадиазола.
Смешивают 0,1 мол 5-амино-1,2,3-тиадиазола и 0,106 мол 3-хлорфенилизоцианата в 75 мл тетрагидрофурана, добавл ют 0,1 мл триэтиламина в качестве катализатора. Выдерживают в течение ночи, отсасывают кристаллы , промывают изопропанолом.
Точка текучести 244°С (с разложением), выход 67,57о от теоретического.
C9H7C1N4OS. Молекул рный вес 254,72.
Найдено, %: 42,87 С; 3,01 Н; 21,51 N.
Пример 5. Получение 5-(К-4-метилфенилкарбамоиламино )-1,2,3-тиадиазола.
Смешивают 0,1 мол 5-амино-1,2,3-тиадиазола и 0,106 мол 4-метилфенилизоцианата в 75 мл тетрагидрофурана, добавл ют 0,1 мл триэтиламина в качестве катализатора. Выдерживают в течение ночи, отсасывают кристаллы , промывают изопропанолом. Точка текучести 228°С (с разложением), выход 55,5% от теоретического.
CioHioN4OS. Молекул рный вес 234,29.
Найдено, %: 50,40 С; 4,65 Н; 23,81 N.
Пример 6. Получение 5-(Ы-3-метилфенилкарбамоиламино )-1,2,3-тиадиазола.
Смешивают 0,1 мол 5-амино-1,2,3-тиадиазола и 0,106 мол 3-метилфенилизоцианата в 75 мл тетрагидрофурана, добавл ют 0,1 мл триэтиламина в качестве катализатора. Выдерживают в течение ночи, отсасывают кристаллы , промывают изопропанолом. Точка текучести 208°С (с разложением), выход 38,5% от теоретического.
CioHic N4OS. Молекул рный вес 234,29.
Найдено, %: 51,44 С; 4,64 Н; 23,75 N.
Пример 7. Получение 5-(N-3,4-диxлopфeнилкарбамоиламино ) -1,2,3-тиадиазола.
Смешивают 0,1 мол 5-амино-1,2,3-тиадиазола и 0,106 мол 3,4-дихлорфенилизоцианата в 75 мл тетрагидрофурана, добавл ют 0,1 мл триэтиламина в качестве катализатора. После сто ни в течение ночи отсасывают кристаллы , промывают изопропанолом. Точка текучести 236°С {с разложением), выход 80,5% от теоретического.
C9H6C12N4OS. Молекул рный вес 289,16.
Найдено, %: 37,40 С; 2,40 Н; 19,39 N.
Полученные кристаллические вешества плохо раствор ютс , например, в алифатических и ароматических углеводородах и в воде и в зависимости от соответствующего замеш,ени хорошо раствор ютс в пол рных органических растворител х, например ацетоне, изофороне , диметилсульфоксиде и диметилформамиде .
Claims (2)
1.Вейганд-Хильгетаг. Методы эксперимента в органической химии, «Хими , 1968,
с. 377.
2.Патент США № 2756135, кл. 260-306.7, 1956.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2214632A DE2214632C2 (de) | 1972-03-23 | 1972-03-23 | Substituierte Carbamoylamino-1,2,3-thiadiazolderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU528875A3 true SU528875A3 (ru) | 1976-09-15 |
Family
ID=5840145
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1895803A SU555824A3 (ru) | 1972-03-23 | 1973-03-19 | Средство дл регулировани роста растений |
| SU1959282A SU528875A3 (ru) | 1972-03-23 | 1973-09-20 | Способ получени производных 1,2,3тиадиазола |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1895803A SU555824A3 (ru) | 1972-03-23 | 1973-03-19 | Средство дл регулировани роста растений |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US3883547A (ru) |
| JP (2) | JPS5242853B2 (ru) |
| AR (1) | AR194650A1 (ru) |
| AT (1) | AT321027B (ru) |
| BE (1) | BE797245A (ru) |
| BG (1) | BG20066A3 (ru) |
| BR (1) | BR7301927D0 (ru) |
| CA (1) | CA1002527A (ru) |
| CH (1) | CH578316A5 (ru) |
| CS (1) | CS168026B2 (ru) |
| CY (1) | CY878A (ru) |
| DD (1) | DD103124A5 (ru) |
| DE (1) | DE2214632C2 (ru) |
| DK (1) | DK131962C (ru) |
| EG (1) | EG11005A (ru) |
| ES (1) | ES411618A1 (ru) |
| FI (1) | FI55837C (ru) |
| FR (1) | FR2177036B1 (ru) |
| GB (1) | GB1426960A (ru) |
| HU (1) | HU166317B (ru) |
| IE (1) | IE37438B1 (ru) |
| IL (1) | IL41848A (ru) |
| IT (1) | IT979104B (ru) |
| KE (1) | KE2670A (ru) |
| LU (1) | LU67254A1 (ru) |
| NL (1) | NL7304073A (ru) |
| PH (1) | PH9442A (ru) |
| PL (1) | PL88474B1 (ru) |
| RO (1) | RO62879A (ru) |
| SE (1) | SE390168B (ru) |
| SU (2) | SU555824A3 (ru) |
| TR (1) | TR20457A (ru) |
| YU (1) | YU34884B (ru) |
| ZA (1) | ZA732045B (ru) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2324732C2 (de) * | 1973-05-14 | 1983-06-01 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | N-Phenyl-N'-1,2,3-thiadiazol-5-yl-thioharnstoff, wuchsregulatorisches Mittel enthaltend diese Verbindung sowie Verfahren zu ihrer Herstellung |
| DE2506690A1 (de) * | 1975-02-14 | 1976-09-02 | Schering Ag | Mittel zur entblaetterung von pflanzen |
| DE2619861C2 (de) * | 1976-05-03 | 1985-05-09 | Schering AG, 1000 Berlin und 4709 Bergkamen | 1-(2-Pyridyl)-3-(1,2,3-thiadiazol-5-yl)-harnstoff sowie diesen enthaltende Mittel zur Wachstumsregulierung und zur Entlbätterung von Pflanzen |
| DE2646712A1 (de) * | 1976-10-14 | 1978-04-20 | Schering Ag | Mittel zur pflanzenwachstumsregulierung |
| DE2716324A1 (de) * | 1977-04-07 | 1978-10-12 | Schering Ag | 1,2,3-thiadiazol-3-in-5-yliden- harnstoffe, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit wachstumsregulatorischer wirkung fuer pflanzen |
| DE2719810A1 (de) * | 1977-04-28 | 1978-11-02 | Schering Ag | 1,2,3-thiadiazolin-2-id-derivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit wachstumsregulatorischer wirkung fuer pflanzen |
| DE2728523C2 (de) * | 1977-06-23 | 1986-02-27 | Schering AG, 1000 Berlin und 4709 Bergkamen | 4-Methyl-1,2,3-thiadiazol-5-carbonsäure-(cyclohexylmethyl)-amid, Mittel mit herbizider und wachstumsregulatorischer Wirkung enthaltend diese Verbindung sowie Verfahren zu seiner Herstellung |
| DE2841825A1 (de) | 1978-09-22 | 1980-04-03 | Schering Ag | Verfahren zur herstellung von 1,2,3- thiadiazol-5-yl-harnstoffen |
| DE2848330A1 (de) | 1978-11-03 | 1980-05-14 | Schering Ag | Verfahren zur herstellung von 1,2, 3-thiadiazol-5-yl-harnstoffen |
| US4253864A (en) * | 1979-07-23 | 1981-03-03 | Monsanto Company | Substituted-1,2,3-thiadiazole-safening agents |
| DE3139506A1 (de) * | 1981-10-01 | 1983-04-21 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 1,2,3-thiadiazol-5-yl-harnstoff-derivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit wuchsregulatorischer und entblaetternder wirkung |
| DE3139505A1 (de) * | 1981-10-01 | 1983-04-21 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 1,2,3,-thiadiazol-5-yl-harnstoff-derivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit wuchsregulatorischer und entblaetternder wirkung |
| DE3319008A1 (de) * | 1983-05-20 | 1984-11-22 | Schering AG, 1000 Berlin und 4709 Bergkamen | 1,2,3-thiadiazol-3-in-5-yliden-harnstoffderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit wuchsregulatorischer und entblaetternder wirkung |
| JPH0223441U (ru) * | 1988-07-29 | 1990-02-16 | ||
| US5238905A (en) * | 1991-10-28 | 1993-08-24 | Union Oil Company Of California | Plant control composition and methods of use with thidiazuron and monocarbamide dihydrogen sulfate |
| US5221659A (en) * | 1991-10-28 | 1993-06-22 | Union Oil Company Of California | Plant control composition and methods of use |
| WO2016037595A1 (en) * | 2014-09-09 | 2016-03-17 | Ustav Experimentalni Botaniky Av Cr, V.V.I. | 1,2,3-thiadiazol-5yl-urea derivatives, use thereof for regulating plant senescence and preparations containing these derivatives |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6902637A (ru) * | 1969-02-19 | 1970-08-21 | ||
| US3787434A (en) * | 1972-03-27 | 1974-01-22 | Fmc Corp | Herbicidal 1,2,3-thiadiazol-5-yl ureas |
-
1972
- 1972-02-19 DD DD168929*A patent/DD103124A5/xx unknown
- 1972-03-23 DE DE2214632A patent/DE2214632C2/de not_active Expired
-
1973
- 1973-02-02 BG BG022594A patent/BG20066A3/xx unknown
- 1973-02-07 TR TR20457A patent/TR20457A/xx unknown
- 1973-02-08 DK DK68973*#A patent/DK131962C/da not_active IP Right Cessation
- 1973-02-08 YU YU324/73A patent/YU34884B/xx unknown
- 1973-02-14 CS CS1076A patent/CS168026B2/cs unknown
- 1973-02-14 ES ES411618A patent/ES411618A1/es not_active Expired
- 1973-02-14 IT IT20383/73A patent/IT979104B/it active
- 1973-02-26 US US335661A patent/US3883547A/en not_active Expired - Lifetime
- 1973-02-27 FI FI591/73A patent/FI55837C/fi active
- 1973-03-06 CA CA165,313A patent/CA1002527A/en not_active Expired
- 1973-03-16 AT AT235573A patent/AT321027B/de not_active IP Right Cessation
- 1973-03-19 EG EG103/73A patent/EG11005A/xx active
- 1973-03-19 GB GB1306573A patent/GB1426960A/en not_active Expired
- 1973-03-19 BR BR731927A patent/BR7301927D0/pt unknown
- 1973-03-19 SU SU1895803A patent/SU555824A3/ru active
- 1973-03-19 CY CY878A patent/CY878A/xx unknown
- 1973-03-20 PH PH14451*UA patent/PH9442A/en unknown
- 1973-03-20 RO RO7300074235A patent/RO62879A/ro unknown
- 1973-03-21 IE IE459/73A patent/IE37438B1/xx unknown
- 1973-03-21 LU LU67254A patent/LU67254A1/xx unknown
- 1973-03-22 HU HUSCHE427*1A patent/HU166317B/hu not_active IP Right Cessation
- 1973-03-22 JP JP48033051A patent/JPS5242853B2/ja not_active Expired
- 1973-03-22 PL PL1973161416A patent/PL88474B1/pl unknown
- 1973-03-22 SE SE7304074A patent/SE390168B/xx unknown
- 1973-03-22 IL IL41848A patent/IL41848A/en unknown
- 1973-03-22 FR FR7310280A patent/FR2177036B1/fr not_active Expired - Fee Related
- 1973-03-23 NL NL7304073A patent/NL7304073A/xx not_active Application Discontinuation
- 1973-03-23 BE BE129188A patent/BE797245A/xx not_active IP Right Cessation
- 1973-03-23 ZA ZA732045A patent/ZA732045B/xx unknown
- 1973-03-23 CH CH428973A patent/CH578316A5/xx not_active IP Right Cessation
- 1973-03-23 AR AR247207A patent/AR194650A1/es active
- 1973-09-20 SU SU1959282A patent/SU528875A3/ru active
-
1976
- 1976-09-06 JP JP51106595A patent/JPS5265271A/ja active Granted
- 1976-10-28 KE KE2670A patent/KE2670A/xx unknown
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