SU458127A3 - Способ получени 1,3,4-тиадиазолил-5-мочевины - Google Patents
Способ получени 1,3,4-тиадиазолил-5-мочевиныInfo
- Publication number
- SU458127A3 SU458127A3 SU1815021A SU1815021A SU458127A3 SU 458127 A3 SU458127 A3 SU 458127A3 SU 1815021 A SU1815021 A SU 1815021A SU 1815021 A SU1815021 A SU 1815021A SU 458127 A3 SU458127 A3 SU 458127A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- thiadiazolyl
- urea
- alkyl
- producing
- general formula
- Prior art date
Links
- 239000004202 carbamide Substances 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- -1 oxy- Chemical group 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 125000005332 alkyl sulfoxy group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000005140 aralkylsulfonyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 description 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 150000003672 ureas Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681816568 DE1816568C3 (de) | 1968-12-23 | 2-Alkylsulfonyl-l,3,4-thiadiazol-5yl-harnstoffe, ihre Verwendung als Herbizide und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU458127A3 true SU458127A3 (ru) | 1975-01-25 |
Family
ID=5717197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1815021A SU458127A3 (ru) | 1968-12-23 | 1969-12-16 | Способ получени 1,3,4-тиадиазолил-5-мочевины |
Country Status (19)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5087284A (en) * | 1968-02-01 | 1992-02-11 | Rhone-Poulenc, Inc. | 5-substituted thiadiazole ureas and their use as herbicides |
| US4182712A (en) * | 1968-02-01 | 1980-01-08 | Mobil Oil Corporation | 5-Substituted thiadiazole ureas |
| US4412079A (en) * | 1968-03-13 | 1983-10-25 | Air Products And Chemicals, Inc. | Thiadiazole compounds and methods of using said compounds in agriculture |
| CH502762A (de) * | 1968-07-17 | 1971-02-15 | Agripat Sa | Neue Thiadiazolyl-harnstoffe enthaltendes herbizides Mittel |
| CA931961A (en) * | 1970-04-17 | 1973-08-14 | Gulf Research And Development Company | Combating unwanted vegetation with 1,3,4-thiadiazolylureas |
| DE2044442C2 (de) * | 1970-09-03 | 1983-11-03 | Schering AG, 1000 Berlin und 4709 Bergkamen | 1,1,3-Trimethyl-3-(-5-Äthylsulfonyl-1,3,4-Thiadiazol-2-yl)-Harnstoff mit herbizider Wirkung |
| DE2601987A1 (de) * | 1976-01-16 | 1977-07-21 | Schering Ag | (5-alkylureido-1,3,4-thiadiazol-2- yl-thio)-essigsaeureester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
| US4217459A (en) | 1976-06-30 | 1980-08-12 | Gulf Oil Corporation | Benzylthio-1,3,4-thiadiazol-2-yl ureas |
| NZ184250A (en) * | 1976-06-30 | 1978-07-10 | Gulf Oil Corp | Certain 1,3-dimethyl-3-(5-substitutedbenzyl thio-1,3,4-thiadiazol-2-yl)-ureas as selective postemergent herbicides for soyabean crops |
| FR2377391A1 (fr) * | 1977-01-17 | 1978-08-11 | Schering Ag | Derives d'acides thiadiazolyl-sulfonyl-acetiques doues de proprietes herbicides |
| US4271166A (en) * | 1977-08-15 | 1981-06-02 | Eli Lilly And Company | N-(1,3,4-Thiadiazol-2-yl)benzamides |
| US4346225A (en) | 1981-06-15 | 1982-08-24 | Eli Lilly And Company | Herbicidal 2-methylamino thiadiazolines |
| US4338449A (en) | 1981-06-15 | 1982-07-06 | Eli Lilly And Company | Herbicidal thiadiazolines |
| US4528022A (en) * | 1983-11-15 | 1985-07-09 | Uniroyal, Inc. | Defoliating composition |
-
1969
- 1969-11-17 CH CH1714869A patent/CH521711A/de not_active IP Right Cessation
- 1969-11-26 GB GB1297147D patent/GB1297147A/en not_active Expired
- 1969-11-26 CY CY834A patent/CY834A/xx unknown
- 1969-11-28 CS CS786669A patent/CS154289B2/cs unknown
- 1969-12-04 RO RO61762A patent/RO56288A/ro unknown
- 1969-12-08 IL IL6933499A patent/IL33499A/xx unknown
- 1969-12-10 YU YU3094/69A patent/YU34529B/xx unknown
- 1969-12-11 FI FI3604/69A patent/FI54304C/fi active
- 1969-12-16 SU SU1815021A patent/SU458127A3/ru active
- 1969-12-22 AT AT1194169A patent/AT299603B/de not_active IP Right Cessation
- 1969-12-22 AT AT702171A patent/AT310184B/de not_active IP Right Cessation
- 1969-12-22 DK DK679169AA patent/DK127787B/da unknown
- 1969-12-22 NL NL6919203A patent/NL167963C/xx not_active IP Right Cessation
- 1969-12-22 SE SE17729/69A patent/SE364964B/xx unknown
- 1969-12-23 JP JP10330669A patent/JPS5327338B1/ja active Pending
- 1969-12-23 FR FR6944722A patent/FR2026977A1/fr active Pending
- 1969-12-23 BE BE743615A patent/BE743615A/xx not_active IP Right Cessation
-
1973
- 1973-12-31 MY MY1973295A patent/MY7300295A/xx unknown
-
1975
- 1975-12-02 KE KE2588*UA patent/KE2588A/xx unknown
-
1980
- 1980-06-20 GT GT198064039A patent/GT198064039A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL167963B (nl) | 1981-09-16 |
| YU309469A (en) | 1979-02-28 |
| GT198064039A (es) | 1981-12-12 |
| JPS5327338B1 (enrdf_load_stackoverflow) | 1978-08-08 |
| DE1816568A1 (de) | 1970-11-05 |
| CH521711A (de) | 1972-04-30 |
| YU34529B (en) | 1979-09-10 |
| NL167963C (nl) | 1982-02-16 |
| IL33499A (en) | 1975-07-28 |
| FI54304B (fi) | 1978-07-31 |
| MY7300295A (en) | 1973-12-31 |
| CY834A (en) | 1976-09-10 |
| RO56288A (enrdf_load_stackoverflow) | 1974-06-01 |
| FI54304C (fi) | 1978-11-10 |
| SU403189A3 (enrdf_load_stackoverflow) | 1973-10-19 |
| SE364964B (enrdf_load_stackoverflow) | 1974-03-11 |
| GB1297147A (enrdf_load_stackoverflow) | 1972-11-22 |
| NL6919203A (enrdf_load_stackoverflow) | 1970-06-25 |
| IL33499A0 (en) | 1970-02-19 |
| CS154289B2 (enrdf_load_stackoverflow) | 1974-03-29 |
| FR2026977A1 (enrdf_load_stackoverflow) | 1970-09-25 |
| DK127787B (da) | 1974-01-07 |
| AT310184B (de) | 1973-09-25 |
| AT299603B (de) | 1972-06-26 |
| BE743615A (enrdf_load_stackoverflow) | 1970-06-23 |
| DE1816568B2 (de) | 1977-02-03 |
| KE2588A (en) | 1975-12-19 |
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