DE2341816A1 - Herbizide 1,3,4-thiadiazol-2-ylharnstoffe - Google Patents
Herbizide 1,3,4-thiadiazol-2-ylharnstoffeInfo
- Publication number
- DE2341816A1 DE2341816A1 DE19732341816 DE2341816A DE2341816A1 DE 2341816 A1 DE2341816 A1 DE 2341816A1 DE 19732341816 DE19732341816 DE 19732341816 DE 2341816 A DE2341816 A DE 2341816A DE 2341816 A1 DE2341816 A1 DE 2341816A1
- Authority
- DE
- Germany
- Prior art keywords
- thiadiazol
- urea
- dimethyl
- august
- trimethylurea
- 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.)
- Ceased
Links
- -1 1,3,4-THIADIAZOL-2-YL Chemical class 0.000 title claims description 46
- 239000004009 herbicide Substances 0.000 title claims description 5
- 239000000463 material Substances 0.000 title 1
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- 239000004202 carbamide Substances 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 16
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000007800 oxidant agent Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
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- YEXIGDOOPPENOC-UHFFFAOYSA-N phenyl hydrogen carbonate;hydrochloride Chemical compound Cl.OC(=O)OC1=CC=CC=C1 YEXIGDOOPPENOC-UHFFFAOYSA-N 0.000 claims description 3
- LLPHPCMDONGDIF-UHFFFAOYSA-N phenylsulfanylformic acid Chemical compound OC(=O)SC1=CC=CC=C1 LLPHPCMDONGDIF-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 229940057054 1,3-dimethylurea Drugs 0.000 claims description 2
- NYFGXMXNGVKYPK-UHFFFAOYSA-N 1-(5-butylsulfanyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylurea Chemical compound CCCCSC1=NN=C(N(C)C(=O)NC)S1 NYFGXMXNGVKYPK-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- XDFOWICGXBXLOG-UHFFFAOYSA-N 1,3-dimethyl-1-[5-(3-methylbutylsulfanyl)-1,3,4-thiadiazol-2-yl]urea Chemical compound CN(C(=O)NC)C=1SC(=NN1)SCCC(C)C XDFOWICGXBXLOG-UHFFFAOYSA-N 0.000 claims 1
- YAFRZTCVUQQSEH-UHFFFAOYSA-N 1-(5-butylsulfanyl-1,3,4-thiadiazol-2-yl)-1,3,3-trimethylurea Chemical compound CCCCSC1=NN=C(N(C)C(=O)N(C)C)S1 YAFRZTCVUQQSEH-UHFFFAOYSA-N 0.000 claims 1
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- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
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- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003560 thiocarbamic acids Chemical class 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- 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
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (29)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732341816 DE2341816A1 (de) | 1973-08-16 | 1973-08-16 | Herbizide 1,3,4-thiadiazol-2-ylharnstoffe |
| DK376974A DK137574C (da) | 1973-08-16 | 1974-07-12 | Herbicide 1,3,4-thiadiazol-2-yl-urinstoffer |
| YU2090/74A YU36941B (en) | 1973-08-16 | 1974-07-26 | Process for obtaining new thiadizolyl-carbamides |
| CS5357A CS174784B2 (enrdf_load_stackoverflow) | 1973-08-16 | 1974-07-26 | |
| ES428822A ES428822A1 (es) | 1973-08-16 | 1974-07-31 | Procedimiento para la preparacion de 1,3,4-tiadiazol-2-il- ureas herbicidas. |
| IT26097/74A IT1054180B (it) | 1973-08-16 | 1974-08-07 | 1.3.4 tiadiazol 2il carbammidi ad azione erbicida |
| GB35427/74A GB1484578A (en) | 1973-08-16 | 1974-08-12 | Herbicidally active 1,3,4-thiadiazole-2-yl-ureas |
| PL1974173423A PL91496B1 (enrdf_load_stackoverflow) | 1973-08-16 | 1974-08-12 | |
| RO7486864A RO69913A (ro) | 1973-08-16 | 1974-08-13 | Procedeu pentru prepararea derivatilor de 1,3,4-tiadiazol-2-il-uree |
| IE1693/74A IE39736B1 (en) | 1973-08-16 | 1974-08-13 | Herbididally active 1,3,4-thiaduazol-2yl-ureas |
| LU70737A LU70737A1 (enrdf_load_stackoverflow) | 1973-08-16 | 1974-08-14 | |
| EG336/74A EG11233A (en) | 1973-08-16 | 1974-08-14 | Herbicidally active 1,3,4 thiadiazol-2-yl ureas |
| FR7428223A FR2240922B1 (enrdf_load_stackoverflow) | 1973-08-16 | 1974-08-14 | |
| DD180502A DD113301A5 (enrdf_load_stackoverflow) | 1973-08-16 | 1974-08-14 | |
| BR6719/74A BR7406719D0 (pt) | 1973-08-16 | 1974-08-15 | Processo para a preparacao de 1,3,4-tiadiazol-2-il-ureias e composicoes herbicidas a base destas |
| SE7410416A SE420723B (sv) | 1973-08-16 | 1974-08-15 | 1,3,4-tiadiazol-2-yl-karbamider till anvendning som herbicida medel |
| CH1115374A CH604496A5 (enrdf_load_stackoverflow) | 1973-08-16 | 1974-08-15 | |
| HU74SC00000489A HU170902B (hu) | 1973-08-16 | 1974-08-15 | Sposob poluchenija 1,3,4-tiadiazol-2-il-karbamidov, i gerbicidy soderzhahhie ikh aktivnymi agentami |
| AU72404/74A AU489033B2 (en) | 1973-08-16 | 1974-08-15 | HERDICIDAL l, 3, 4-THIADIAZOL-2-YL-UREAS |
| AT671274A AT338038B (de) | 1973-08-16 | 1974-08-16 | Selektive herbizide mittel |
| JP49094100A JPS5048138A (enrdf_load_stackoverflow) | 1973-08-16 | 1974-08-16 | |
| NL7410979A NL7410979A (nl) | 1973-08-16 | 1974-08-16 | Werkwijze ter bereiding van een herbicide middel. |
| FI2431/74A FI243174A7 (enrdf_load_stackoverflow) | 1973-08-16 | 1974-08-16 | |
| ZA00745283A ZA745283B (en) | 1973-08-16 | 1974-08-16 | Herbicidally active 1,3,4-thiadiazol-2-yl-ureas |
| SU742054687A SU632302A3 (ru) | 1973-08-16 | 1974-08-16 | Способ получени 1,3,4-тиадиазол-2илмочевин |
| SU7402053277A SU576892A3 (ru) | 1973-08-16 | 1974-08-16 | Гербицидный состав |
| BE147657A BE818908A (fr) | 1973-08-16 | 1974-08-16 | 1,3,4-thiadiazol-2-yl-urees herbicides et leur procede de preparation |
| PH16185A PH12166A (en) | 1973-08-16 | 1974-08-16 | Herbicidally active l,3,4-thiadiazol-2-yl ureas |
| IL45479A IL45479A (en) | 1973-08-16 | 1974-08-16 | Herbicidally active 1,3-dimethyl-3-(5-alkylthio-1,3,4-thiadiazol-2-yl) urea derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732341816 DE2341816A1 (de) | 1973-08-16 | 1973-08-16 | Herbizide 1,3,4-thiadiazol-2-ylharnstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2341816A1 true DE2341816A1 (de) | 1975-02-27 |
Family
ID=5890103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732341816 Ceased DE2341816A1 (de) | 1973-08-16 | 1973-08-16 | Herbizide 1,3,4-thiadiazol-2-ylharnstoffe |
Country Status (27)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2741394A1 (de) * | 1977-08-29 | 1979-03-22 | Lilly Co Eli | Herbizide mittel |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2607481A1 (de) * | 1976-02-20 | 1977-08-25 | Schering Ag | 2-dimethylcarbamoylimino-1,3,4- thiadiazolin-3-id-derivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
| US4066436A (en) * | 1976-06-30 | 1978-01-03 | Gulf Oil Corporation | Method of controlling sicklepod in soybeans |
| IT1255219B (it) * | 1992-07-14 | 1995-10-20 | Ct Lab Farm Srl | Derivati del tiadiazolo per la cura degli stati depressivi |
-
1973
- 1973-08-16 DE DE19732341816 patent/DE2341816A1/de not_active Ceased
-
1974
- 1974-07-12 DK DK376974A patent/DK137574C/da not_active IP Right Cessation
- 1974-07-26 CS CS5357A patent/CS174784B2/cs unknown
- 1974-07-26 YU YU2090/74A patent/YU36941B/xx unknown
- 1974-07-31 ES ES428822A patent/ES428822A1/es not_active Expired
- 1974-08-07 IT IT26097/74A patent/IT1054180B/it active
- 1974-08-12 PL PL1974173423A patent/PL91496B1/pl unknown
- 1974-08-12 GB GB35427/74A patent/GB1484578A/en not_active Expired
- 1974-08-13 IE IE1693/74A patent/IE39736B1/xx unknown
- 1974-08-13 RO RO7486864A patent/RO69913A/ro unknown
- 1974-08-14 DD DD180502A patent/DD113301A5/xx unknown
- 1974-08-14 FR FR7428223A patent/FR2240922B1/fr not_active Expired
- 1974-08-14 LU LU70737A patent/LU70737A1/xx unknown
- 1974-08-14 EG EG336/74A patent/EG11233A/xx active
- 1974-08-15 BR BR6719/74A patent/BR7406719D0/pt unknown
- 1974-08-15 HU HU74SC00000489A patent/HU170902B/hu unknown
- 1974-08-15 CH CH1115374A patent/CH604496A5/xx not_active IP Right Cessation
- 1974-08-15 SE SE7410416A patent/SE420723B/xx unknown
- 1974-08-16 JP JP49094100A patent/JPS5048138A/ja active Pending
- 1974-08-16 BE BE147657A patent/BE818908A/xx not_active IP Right Cessation
- 1974-08-16 ZA ZA00745283A patent/ZA745283B/xx unknown
- 1974-08-16 FI FI2431/74A patent/FI243174A7/fi unknown
- 1974-08-16 NL NL7410979A patent/NL7410979A/xx not_active Application Discontinuation
- 1974-08-16 PH PH16185A patent/PH12166A/en unknown
- 1974-08-16 AT AT671274A patent/AT338038B/de not_active IP Right Cessation
- 1974-08-16 SU SU7402053277A patent/SU576892A3/ru active
- 1974-08-16 SU SU742054687A patent/SU632302A3/ru active
- 1974-08-16 IL IL45479A patent/IL45479A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2741394A1 (de) * | 1977-08-29 | 1979-03-22 | Lilly Co Eli | Herbizide mittel |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8131 | Rejection |