IL43985A - 3-(1,3,4-thiadiazol-2-yl)-5-hydroxy-hydantoins,their preparation and herbicidal compositions containing them - Google Patents
3-(1,3,4-thiadiazol-2-yl)-5-hydroxy-hydantoins,their preparation and herbicidal compositions containing themInfo
- Publication number
- IL43985A IL43985A IL43985A IL4398574A IL43985A IL 43985 A IL43985 A IL 43985A IL 43985 A IL43985 A IL 43985A IL 4398574 A IL4398574 A IL 4398574A IL 43985 A IL43985 A IL 43985A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- represents alkyl
- compound
- admixture
- carrier
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims 4
- 230000002363 herbicidal effect Effects 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract 7
- 239000000852 hydrogen donor Substances 0.000 claims abstract 3
- 239000003054 catalyst Substances 0.000 claims abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract 2
- 239000002798 polar solvent Substances 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims 8
- 239000003085 diluting agent Substances 0.000 claims 4
- 241000196324 Embryophyta Species 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- ZFLIKDUSUDBGCD-UHFFFAOYSA-N parabanic acid Chemical class O=C1NC(=O)C(=O)N1 ZFLIKDUSUDBGCD-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000012280 lithium aluminium hydride Substances 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 abstract 2
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 abstract 1
- RMSGOOXIXALDQM-UHFFFAOYSA-N 1-methyl-3-(1,3,4-thiadiazol-2-yl)urea Chemical compound CNC(=O)NC1=NN=CS1 RMSGOOXIXALDQM-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 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)
- 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]
Claims (5)
1. 43985/2 What we claim is: 1. 3-(l»3, 4-Thiadiazol-2-yl)-5-hydroxy-hydantoins of the general formula in which R represents alkyl with 1 to 6 carbon atoms , and R^ represents alkyl.
2. Compounds according to claim 1 in which R represents alkyl with 1 to 6 carbon atoms; and R^ represents alkyl with 1 to 5 carbon atoms.
3. The compound of the formula formula 43985/2 5. A process for the production of a 3-(l,3>4-thiad-iazol-2-yl)-5-hydroxy-hydantoins according to any of claims 1-X in which a parabanic acid derivative of the general formula 0 0 N N |! Li II 0 in which R and R^" have the meanings given in claim 1, is reacted with hydrogen in the presence of a hydrogenation catalyst, or with a hydrogen donor in the presence of a polar solvent . 6. A process according to claim 5 in which the parabanic acid is any of those hereinbefore specifically identified. 7. A process according to claim 5 or 6 in which sodium borohydride or lithium aluminium hydride is used as hydrogen donor. 8. A process according to any of claims 5 to 7 in which the reaction is carried out at -20 to +20°C. 9. A process for the productio f a compound according to claim 1, substantiallj'- as hereinbefore described in any of Examples 1 and 2. 10. Compounds according to claim 1 whenever prepared by a process according to any of cl ims 5 to 9. 11. A herbicidal composition containing as active in- Le A 14 788 - IS - L0- 43985/2 gredient a compound according to any of claims 1 to 4 or 10 in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent. 12. A composition according to claim 11 containing from 0.1 to S5% of the active compound by weight. 13. A method of combating weeds which comprises applying to the weeds or their habitat a compound according to any of claims 1 to 4 or 10 alone or in the form of a composition containing as active ingredient a compound according to any of claims 1 to 4 or 10 in admixture with a diluent or carrier. 1
4. A method according to claim 13 in which the active compound is applied to an area of agriculture in an amount of 0.1 to 25 kg per hectare. 1
5. Crops protected from damage by weeds by being grown in areas in which, immediately prior to and/or during the time of the growing, a compound according to any of claims 1 to 4 or 10 was applied alone or in admixture with a diluent or carrier. - 1.9J -
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 |
|---|---|
| IL43985A0 IL43985A0 (en) | 1974-05-16 |
| IL43985A true IL43985A (en) | 1976-08-31 |
Family
ID=5868976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL43985A IL43985A (en) | 1973-01-13 | 1974-01-10 | 3-(1,3,4-thiadiazol-2-yl)-5-hydroxy-hydantoins,their preparation and herbicidal compositions containing them |
Country Status (24)
| Country | Link |
|---|---|
| JP (2) | JPS49108243A (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 AU AU64350/74A patent/AU473738B2/en not_active Expired
- 1974-01-09 RO RO7400077228A patent/RO63661A/en unknown
- 1974-01-09 BR BR106/74A patent/BR7400106D0/en unknown
- 1974-01-10 NL NL7400355A patent/NL7400355A/xx not_active Application Discontinuation
- 1974-01-10 TR TR17381A patent/TR17381A/en unknown
- 1974-01-10 IL IL43985A patent/IL43985A/en unknown
- 1974-01-10 LU LU69140A patent/LU69140A1/xx unknown
- 1974-01-11 DK DK15474A patent/DK136068C/en active
- 1974-01-11 GB GB137374A patent/GB1445912A/en not_active Expired
- 1974-01-11 HU HUBA3014A patent/HU168897B/hu unknown
- 1974-01-11 FR FR7400966A patent/FR2213942B1/fr not_active Expired
- 1974-01-11 IE IE64/74A patent/IE38734B1/en unknown
- 1974-01-11 BE BE139718A patent/BE809638A/en unknown
- 1974-01-11 PL PL1974168055A patent/PL88499B1/pl unknown
- 1974-01-11 CA CA189,989A patent/CA1029731A/en not_active Expired
- 1974-01-11 CH CH39374A patent/CH584709A5/xx not_active IP Right Cessation
- 1974-01-11 DD DD175961A patent/DD110742A5/xx unknown
- 1974-01-11 AT AT23474*#A patent/AT328218B/en not_active IP Right Cessation
- 1974-01-12 JP JP49006359A patent/JPS49108243A/ja active Pending
- 1974-01-12 JP JP49006358A patent/JPS49108077A/ja active Pending
- 1974-01-12 ES ES422258A patent/ES422258A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK136068C (en) | 1978-01-16 |
| IE38734B1 (en) | 1978-05-24 |
| IL43985A0 (en) | 1974-05-16 |
| CA1029731A (en) | 1978-04-18 |
| FR2213942A1 (en) | 1974-08-09 |
| AU473738B2 (en) | 1976-07-01 |
| DD110742A5 (en) | 1975-01-12 |
| TR17381A (en) | 1975-03-24 |
| DE2301704A1 (en) | 1974-07-18 |
| BR7400106D0 (en) | 1974-08-15 |
| JPS49108243A (en) | 1974-10-15 |
| AU6435074A (en) | 1975-07-10 |
| HU168897B (en) | 1976-08-28 |
| ZA74207B (en) | 1974-11-27 |
| JPS49108077A (en) | 1974-10-14 |
| EG11177A (en) | 1977-03-31 |
| GB1445912A (en) | 1976-08-11 |
| RO63661A (en) | 1978-10-15 |
| BE809638A (en) | 1974-07-11 |
| LU69140A1 (en) | 1974-08-19 |
| PL88499B1 (en) | 1976-09-30 |
| SU555826A3 (en) | 1977-04-25 |
| NL7400355A (en) | 1974-07-16 |
| CH584709A5 (en) | 1977-02-15 |
| ES422258A1 (en) | 1976-11-16 |
| ATA23474A (en) | 1975-05-15 |
| DK136068B (en) | 1977-08-08 |
| AT328218B (en) | 1976-03-10 |
| FR2213942B1 (en) | 1977-06-10 |
| IE38734L (en) | 1974-07-13 |
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