DE2301703A1 - 5-acylierte 3-(1,3,4-thiadiazol-2-yl)5-hydroxy-hydantoine, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide - Google Patents
5-acylierte 3-(1,3,4-thiadiazol-2-yl)5-hydroxy-hydantoine, verfahren zu ihrer herstellung sowie ihre verwendung als herbizideInfo
- Publication number
- DE2301703A1 DE2301703A1 DE2301703A DE2301703A DE2301703A1 DE 2301703 A1 DE2301703 A1 DE 2301703A1 DE 2301703 A DE2301703 A DE 2301703A DE 2301703 A DE2301703 A DE 2301703A DE 2301703 A1 DE2301703 A1 DE 2301703A1
- Authority
- DE
- Germany
- Prior art keywords
- thiadiazol
- formula
- methyl
- hydantoins
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 1,3,4-THIADIAZOL-2-YL Chemical class 0.000 title claims description 74
- 238000000034 method Methods 0.000 title claims description 20
- 239000004009 herbicide Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000002904 solvent Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 10
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 7
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 150000001469 hydantoins Chemical class 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 230000008635 plant growth Effects 0.000 claims description 3
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- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 1
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- 125000004432 carbon atom Chemical group C* 0.000 description 18
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- FTYDUPPPGMRNGZ-UHFFFAOYSA-N 3-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-5-hydroxy-1-methylimidazolidine-2,4-dione Chemical compound O=C1N(C)C(O)C(=O)N1C1=NN=C(C(C)(C)C)S1 FTYDUPPPGMRNGZ-UHFFFAOYSA-N 0.000 description 5
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- 239000002244 precipitate Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000036435 stunted growth Effects 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (25)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ZA740208A ZA74208B (en) | 1973-01-13 | 1973-01-11 | 3-(1,3,4-thiadiazol-2-yl)-5-acyloxy(carbamoyloxy)-hydantoins,a process for their preparation and their use as herbicides |
| DE2301703A DE2301703A1 (de) | 1973-01-13 | 1973-01-13 | 5-acylierte 3-(1,3,4-thiadiazol-2-yl)5-hydroxy-hydantoine, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide |
| SU1980521A SU524494A3 (ru) | 1973-01-13 | 1973-12-28 | Гербицидное средство |
| RO7477198A RO65648A (ro) | 1973-01-13 | 1974-01-05 | Procedeu pentru prepararea unor 3-(1,3,4-tiadiazol-2-il)-5-hidroxihidantoine-5-acilate |
| BR188/74A BR7400188D0 (pt) | 1973-01-13 | 1974-01-09 | Idroxihidantoinas, e composicoes herbicidas a base destas processo para a fabricacao de 3-(1,3,4-tiadiazol-2-il)-5- |
| EG6/74A EG11154A (en) | 1973-01-13 | 1974-01-10 | 3-(1,3,4-thiadiazol-2-yl)-5-acyloxy(carbamoyloxy-hydantions,a process for their preparation and their use as herbicides |
| NL7400358A NL7400358A (enrdf_load_stackoverflow) | 1973-01-13 | 1974-01-10 | |
| TR17400A TR17400A (tr) | 1973-01-13 | 1974-01-10 | 5-asillenmis 3-(1,3-4-tiadiazol-2-il)-5-hidroksi hidantoinler,bunlarin hazirlanmasina mahsus usuller ve bunlarin herbisid olarak kullanimalari |
| IL43987A IL43987A (en) | 1973-01-13 | 1974-01-10 | 3-(1,3,4-thiadiazol-2-yl)-5-acyloxy(and carbamoyloxy)-hydantoins,their preparation and herbicidal compositions containing them |
| CA189,955A CA1029730A (en) | 1973-01-13 | 1974-01-11 | 3-(1,3,4-thiadiazol-2-yl)5-acyloxy(carbamoyloxy)-hydantoins, a process for their preparation and their use as herbicides |
| GB137274A GB1445911A (en) | 1973-01-13 | 1974-01-11 | 3-1,3,4-thiadiazol-2-yl-5-acyloxy-carbamoyloxy-hydantoins a process for their preparation and their use as herbicides |
| CH39574A CH604495A5 (enrdf_load_stackoverflow) | 1973-01-13 | 1974-01-11 | |
| FR7400965A FR2213941B1 (enrdf_load_stackoverflow) | 1973-01-13 | 1974-01-11 | |
| HUBA3013A HU167899B (enrdf_load_stackoverflow) | 1973-01-13 | 1974-01-11 | |
| BE139717A BE809637A (fr) | 1973-01-13 | 1974-01-11 | Nouvelles 3-(1,3,4-thiadiazol-2-yl)-5-acyloxy-(carbamoyloxy)-hydantoines, leur procede de preparation et leur application |
| DD175969A DD110743A5 (enrdf_load_stackoverflow) | 1973-01-13 | 1974-01-11 | |
| PL1974168054A PL88500B1 (enrdf_load_stackoverflow) | 1973-01-13 | 1974-01-11 | |
| IE65/74A IE38735B1 (en) | 1973-01-13 | 1974-01-11 | 3-(1,3.j-thiadiazol-2-yl)-5acyloxy-(carbamoyloxy)-hydantoins, a process for their preparation and their use as herbicides |
| LU69146A LU69146A1 (enrdf_load_stackoverflow) | 1973-01-13 | 1974-01-11 | |
| JP49006360A JPS49108078A (enrdf_load_stackoverflow) | 1973-01-13 | 1974-01-12 | |
| JP49006361A JPS49108244A (enrdf_load_stackoverflow) | 1973-01-13 | 1974-01-12 | |
| ES422259A ES422259A1 (es) | 1973-01-13 | 1974-01-12 | Procedimiento para la obtencion de 1,3(1,3,4-tiadiazol-2- il)-5-aciloxi(carbamoiloxi)-hidantoinas. |
| AU64480/74A AU475777B2 (en) | 1973-01-13 | 1974-01-14 | 3-(1,3,4-thiadiazol-2-yl)-5-acyloxy (carbamoyloxy)-hydantoins, a process for their preparation and their use as herbicides |
| AT26374*#A AT329314B (de) | 1973-01-13 | 1974-01-14 | Herbizides mittel |
| US05/804,026 US4154597A (en) | 1973-01-13 | 1977-06-06 | 3-(1,3,4-Thiadiazol-2-yl)-5-acyloxy(carbamoyloxy)-hydantoin compounds and herbicidal compositions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2301703A DE2301703A1 (de) | 1973-01-13 | 1973-01-13 | 5-acylierte 3-(1,3,4-thiadiazol-2-yl)5-hydroxy-hydantoine, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2301703A1 true DE2301703A1 (de) | 1974-07-18 |
Family
ID=5868975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2301703A Pending DE2301703A1 (de) | 1973-01-13 | 1973-01-13 | 5-acylierte 3-(1,3,4-thiadiazol-2-yl)5-hydroxy-hydantoine, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide |
Country Status (23)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2828755A1 (de) * | 1978-06-30 | 1980-01-03 | Bosch Gmbh Robert | Funknetz |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0840556A (ja) * | 1994-08-01 | 1996-02-13 | Makoto Suzuki | 食器供給機 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2013407A1 (de) * | 1970-03-20 | 1971-10-07 | 1 (1,3,4 Thiadiazol 2 yl) lmidazohdi non (2) Derivate, Verfahren zu ihrer Her stellung und ihre Verwendung als herbizide | |
| BE789441A (fr) * | 1971-09-30 | 1973-03-29 | Ciba Geigy | Nouvel herbicide selectif et procede pour sa preparation |
-
1973
- 1973-01-11 ZA ZA740208A patent/ZA74208B/xx unknown
- 1973-01-13 DE DE2301703A patent/DE2301703A1/de active Pending
- 1973-12-28 SU SU1980521A patent/SU524494A3/ru active
-
1974
- 1974-01-05 RO RO7477198A patent/RO65648A/ro unknown
- 1974-01-09 BR BR188/74A patent/BR7400188D0/pt unknown
- 1974-01-10 EG EG6/74A patent/EG11154A/xx active
- 1974-01-10 NL NL7400358A patent/NL7400358A/xx not_active Application Discontinuation
- 1974-01-10 IL IL43987A patent/IL43987A/en unknown
- 1974-01-10 TR TR17400A patent/TR17400A/xx unknown
- 1974-01-11 BE BE139717A patent/BE809637A/xx unknown
- 1974-01-11 CA CA189,955A patent/CA1029730A/en not_active Expired
- 1974-01-11 FR FR7400965A patent/FR2213941B1/fr not_active Expired
- 1974-01-11 DD DD175969A patent/DD110743A5/xx unknown
- 1974-01-11 LU LU69146A patent/LU69146A1/xx unknown
- 1974-01-11 PL PL1974168054A patent/PL88500B1/pl unknown
- 1974-01-11 HU HUBA3013A patent/HU167899B/hu unknown
- 1974-01-11 IE IE65/74A patent/IE38735B1/xx unknown
- 1974-01-11 GB GB137274A patent/GB1445911A/en not_active Expired
- 1974-01-11 CH CH39574A patent/CH604495A5/xx not_active IP Right Cessation
- 1974-01-12 JP JP49006361A patent/JPS49108244A/ja active Pending
- 1974-01-12 ES ES422259A patent/ES422259A1/es not_active Expired
- 1974-01-12 JP JP49006360A patent/JPS49108078A/ja active Pending
- 1974-01-14 AU AU64480/74A patent/AU475777B2/en not_active Expired
- 1974-01-14 AT AT26374*#A patent/AT329314B/de not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2828755A1 (de) * | 1978-06-30 | 1980-01-03 | Bosch Gmbh Robert | Funknetz |
Also Published As
| Publication number | Publication date |
|---|---|
| IL43987A (en) | 1976-08-31 |
| GB1445911A (en) | 1976-08-11 |
| LU69146A1 (enrdf_load_stackoverflow) | 1974-08-19 |
| AU475777B2 (en) | 1976-09-02 |
| IL43987A0 (en) | 1974-05-16 |
| IE38735B1 (en) | 1978-05-24 |
| IE38735L (en) | 1974-07-13 |
| ATA26374A (de) | 1975-07-15 |
| JPS49108244A (enrdf_load_stackoverflow) | 1974-10-15 |
| ZA74208B (en) | 1974-11-27 |
| EG11154A (en) | 1979-03-31 |
| BR7400188D0 (pt) | 1974-08-15 |
| ES422259A1 (es) | 1976-11-01 |
| SU524494A3 (ru) | 1976-08-05 |
| TR17400A (tr) | 1975-03-24 |
| PL88500B1 (enrdf_load_stackoverflow) | 1976-09-30 |
| HU167899B (enrdf_load_stackoverflow) | 1976-01-28 |
| CA1029730A (en) | 1978-04-18 |
| RO65648A (ro) | 1980-06-15 |
| NL7400358A (enrdf_load_stackoverflow) | 1974-07-16 |
| CH604495A5 (enrdf_load_stackoverflow) | 1978-09-15 |
| DD110743A5 (enrdf_load_stackoverflow) | 1975-01-12 |
| FR2213941A1 (enrdf_load_stackoverflow) | 1974-08-09 |
| JPS49108078A (enrdf_load_stackoverflow) | 1974-10-14 |
| AU6448074A (en) | 1975-07-17 |
| FR2213941B1 (enrdf_load_stackoverflow) | 1977-06-10 |
| AT329314B (de) | 1976-05-10 |
| BE809637A (fr) | 1974-07-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |