IE38734B1 - 3-(1,3.4-thiadiazol-2-yl)-5-hydroxyhydantoins, process fortheir preparation and their use as herbicides - Google Patents
3-(1,3.4-thiadiazol-2-yl)-5-hydroxyhydantoins, process fortheir preparation and their use as herbicidesInfo
- Publication number
- IE38734B1 IE38734B1 IE64/74A IE6474A IE38734B1 IE 38734 B1 IE38734 B1 IE 38734B1 IE 64/74 A IE64/74 A IE 64/74A IE 6474 A IE6474 A IE 6474A IE 38734 B1 IE38734 B1 IE 38734B1
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- thiadiazol
- compounds
- herbicides
- represents alkyl
- Prior art date
Links
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1445912 3 - (1,3,4 - Thiadiazol - 2 - yl) - 5- hydroxy-hydantoins BAYER AG 11 Jan 1974 [13 Jan 1973] 01373 Heading C2C Compounds of Formula I wherein R represents alkyl, haloalkyl, alkyl mercapto or alkylsulphonyl and R<SP>1</SP> represents alkyl are prepared by reacting (e.g. at - 20‹ to +20‹ C.) a parabamic acid derivative of Formula II with H 2 in the presence of a hydrogenation catalyst, or with a hydrogen donor (e.g. NaBH 4 , LiAlR 4 ) in the presence of a polar solvent. The compounds of Formula I in which R represents alkyl or C 2-4 alkylmercapto are novel and are claimed per se. Exemplified compounds of Formula I are those in which R<SP>1</SP> is CH 3 or C 2 H 5 and R is t-C 4 H 9 , CF 3 , CH 3 S-, C 2 H 5 S-, n-C 3 H 7 S-, i-C 3 H 7 S-, n-C 4 H 9 S-, or CH 3 SO 2 -. The starting materials of Formula II wherein R<SP>1</SP> is CH 3 and R is t-C 4 H 9 or C 2 H 5 -S- are prepared from oxalyl chloride and the corresponding 1 - methyl - 3 - (1,3,4 - thiadiazol - 2- yl)-urea. The compounds of Formula I are herbicides.
[GB1445912A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2301704A DE2301704A1 (en) | 1973-01-13 | 1973-01-13 | 3- (1,3,4-THIADIAZOL-2-YL) -5-HYDROXYHYDANTOINE, METHOD OF PREPARATION AND USE AS HERBICIDES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE38734L IE38734L (en) | 1974-07-13 |
| IE38734B1 true IE38734B1 (en) | 1978-05-24 |
Family
ID=5868976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE64/74A IE38734B1 (en) | 1973-01-13 | 1974-01-11 | 3-(1,3.4-thiadiazol-2-yl)-5-hydroxyhydantoins, process fortheir preparation and their use as herbicides |
Country Status (24)
| Country | Link |
|---|---|
| JP (2) | JPS49108077A (en) |
| AT (1) | AT328218B (en) |
| AU (1) | AU473738B2 (en) |
| BE (1) | BE809638A (en) |
| BR (1) | BR7400106D0 (en) |
| CA (1) | CA1029731A (en) |
| CH (1) | CH584709A5 (en) |
| DD (1) | DD110742A5 (en) |
| DE (1) | DE2301704A1 (en) |
| DK (1) | DK136068C (en) |
| EG (1) | EG11177A (en) |
| ES (1) | ES422258A1 (en) |
| FR (1) | FR2213942B1 (en) |
| GB (1) | GB1445912A (en) |
| HU (1) | HU168897B (en) |
| IE (1) | IE38734B1 (en) |
| IL (1) | IL43985A (en) |
| LU (1) | LU69140A1 (en) |
| NL (1) | NL7400355A (en) |
| PL (1) | PL88499B1 (en) |
| RO (1) | RO63661A (en) |
| SU (1) | SU555826A3 (en) |
| TR (1) | TR17381A (en) |
| ZA (1) | ZA74207B (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2013418A1 (en) * | 1970-03-20 | 1971-10-07 | I (1,3,4 thiadiazol 2 yl) imidazohdi non (2) derivatives, process for their manufacture and their use as herbicides | |
| BE789441A (en) * | 1971-09-30 | 1973-03-29 | Ciba Geigy | NEW SELECTIVE HERBICIDE AND PROCESS FOR ITS PREPARATION |
-
1973
- 1973-01-11 ZA ZA740207A patent/ZA74207B/en unknown
- 1973-01-13 DE DE2301704A patent/DE2301704A1/en active Pending
- 1973-12-27 EG EG486/73A patent/EG11177A/en active
- 1973-12-28 SU SU1980519A patent/SU555826A3/en active
-
1974
- 1974-01-09 RO RO7400077228A patent/RO63661A/en unknown
- 1974-01-09 BR BR106/74A patent/BR7400106D0/en unknown
- 1974-01-09 AU AU64350/74A patent/AU473738B2/en not_active Expired
- 1974-01-10 LU LU69140A patent/LU69140A1/xx unknown
- 1974-01-10 TR TR17381A patent/TR17381A/en unknown
- 1974-01-10 IL IL43985A patent/IL43985A/en unknown
- 1974-01-10 NL NL7400355A patent/NL7400355A/xx not_active Application Discontinuation
- 1974-01-11 IE IE64/74A patent/IE38734B1/en unknown
- 1974-01-11 AT AT23474*#A patent/AT328218B/en not_active IP Right Cessation
- 1974-01-11 BE BE139718A patent/BE809638A/en unknown
- 1974-01-11 DK DK15474A patent/DK136068C/en active
- 1974-01-11 CA CA189,989A patent/CA1029731A/en not_active Expired
- 1974-01-11 PL PL1974168055A patent/PL88499B1/pl unknown
- 1974-01-11 CH CH39374A patent/CH584709A5/xx not_active IP Right Cessation
- 1974-01-11 GB GB137374A patent/GB1445912A/en not_active Expired
- 1974-01-11 HU HUBA3014A patent/HU168897B/hu unknown
- 1974-01-11 DD DD175961A patent/DD110742A5/xx unknown
- 1974-01-11 FR FR7400966A patent/FR2213942B1/fr not_active Expired
- 1974-01-12 JP JP49006358A patent/JPS49108077A/ja active Pending
- 1974-01-12 JP JP49006359A patent/JPS49108243A/ja active Pending
- 1974-01-12 ES ES422258A patent/ES422258A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU473738B2 (en) | 1976-07-01 |
| JPS49108243A (en) | 1974-10-15 |
| NL7400355A (en) | 1974-07-16 |
| BE809638A (en) | 1974-07-11 |
| TR17381A (en) | 1975-03-24 |
| DK136068C (en) | 1978-01-16 |
| DK136068B (en) | 1977-08-08 |
| CH584709A5 (en) | 1977-02-15 |
| DE2301704A1 (en) | 1974-07-18 |
| BR7400106D0 (en) | 1974-08-15 |
| EG11177A (en) | 1977-03-31 |
| IE38734L (en) | 1974-07-13 |
| AU6435074A (en) | 1975-07-10 |
| GB1445912A (en) | 1976-08-11 |
| IL43985A0 (en) | 1974-05-16 |
| JPS49108077A (en) | 1974-10-14 |
| ZA74207B (en) | 1974-11-27 |
| CA1029731A (en) | 1978-04-18 |
| LU69140A1 (en) | 1974-08-19 |
| SU555826A3 (en) | 1977-04-25 |
| PL88499B1 (en) | 1976-09-30 |
| ATA23474A (en) | 1975-05-15 |
| FR2213942B1 (en) | 1977-06-10 |
| DD110742A5 (en) | 1975-01-12 |
| IL43985A (en) | 1976-08-31 |
| ES422258A1 (en) | 1976-11-16 |
| HU168897B (en) | 1976-08-28 |
| FR2213942A1 (en) | 1974-08-09 |
| AT328218B (en) | 1976-03-10 |
| RO63661A (en) | 1978-10-15 |
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