DE2209010A1 - Unkrautbekämpfungsmittel und Verfahren zur Herstellung derselben - Google Patents
Unkrautbekämpfungsmittel und Verfahren zur Herstellung derselbenInfo
- Publication number
- DE2209010A1 DE2209010A1 DE19722209010 DE2209010A DE2209010A1 DE 2209010 A1 DE2209010 A1 DE 2209010A1 DE 19722209010 DE19722209010 DE 19722209010 DE 2209010 A DE2209010 A DE 2209010A DE 2209010 A1 DE2209010 A1 DE 2209010A1
- Authority
- DE
- Germany
- Prior art keywords
- thiadiazole
- sulfonamide
- methylureido
- dimethylureido
- ethyl
- 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
- 238000000034 method Methods 0.000 title claims description 22
- 239000004009 herbicide Substances 0.000 title description 13
- 241000196324 Embryophyta Species 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 53
- -1 cycloalkyl radicals Chemical class 0.000 claims description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 229940124530 sulfonamide Drugs 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 150000003456 sulfonamides Chemical class 0.000 claims description 11
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 10
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- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 5
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
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- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- MLRBKPMYTYCDOQ-UHFFFAOYSA-N 1-[5-(dimethylsulfamoyl)-1,3,4-thiadiazol-2-yl]-1,3,3-trimethylurea Chemical compound CN(C)C(=O)N(C)C1=NN=C(S(=O)(=O)N(C)C)S1 MLRBKPMYTYCDOQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
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- UDCMVTCBKMAFEI-UHFFFAOYSA-N 1-[5-(cyclopropylsulfamoyl)-1,3,4-thiadiazol-2-yl]-1,3-dimethylurea Chemical compound CN(C(=O)NC)C1=NN=C(S1)S(=O)(=O)NC1CC1 UDCMVTCBKMAFEI-UHFFFAOYSA-N 0.000 claims 1
- BUWXLHZKBCZTMH-UHFFFAOYSA-N 1-[5-(cyclopropylsulfamoyl)-1,3,4-thiadiazol-2-yl]-3-methylurea Chemical compound CNC(NC1=NN=C(S1)S(=O)(=O)NC1CC1)=O BUWXLHZKBCZTMH-UHFFFAOYSA-N 0.000 claims 1
- DNQQQZPWCHQWHW-UHFFFAOYSA-N 1-[5-(diethylsulfamoyl)-1,3,4-thiadiazol-2-yl]-1,3,3-trimethylurea Chemical compound CN(C(=O)N(C)C)C1=NN=C(S1)S(=O)(=O)N(CC)CC DNQQQZPWCHQWHW-UHFFFAOYSA-N 0.000 claims 1
- MGYRCSIVLWTFMH-UHFFFAOYSA-N 1-[5-(diethylsulfamoyl)-1,3,4-thiadiazol-2-yl]-1,3-dimethylurea Chemical compound CCN(CC)S(=O)(=O)C1=NN=C(N(C)C(=O)NC)S1 MGYRCSIVLWTFMH-UHFFFAOYSA-N 0.000 claims 1
- CMTGMVLWNCLAGE-UHFFFAOYSA-N 1-[5-(dimethylsulfamoyl)-1,3,4-thiadiazol-2-yl]-1-ethyl-3-methylurea Chemical compound CNC(=O)N(CC)C1=NN=C(S(=O)(=O)N(C)C)S1 CMTGMVLWNCLAGE-UHFFFAOYSA-N 0.000 claims 1
- ISVORCXSSLIGFG-UHFFFAOYSA-N 1-[5-(dimethylsulfamoyl)-1,3,4-thiadiazol-2-yl]-3-methylurea Chemical compound CNC(=O)NC1=NN=C(S(=O)(=O)N(C)C)S1 ISVORCXSSLIGFG-UHFFFAOYSA-N 0.000 claims 1
- FKJLGQQFOSWNKR-UHFFFAOYSA-N 1-[5-(ethylsulfamoyl)-1,3,4-thiadiazol-2-yl]-3-methylurea Chemical compound CNC(NC1=NN=C(S1)S(=O)(=O)NCC)=O FKJLGQQFOSWNKR-UHFFFAOYSA-N 0.000 claims 1
- BDROSDXBVFYBBA-UHFFFAOYSA-N 1-[5-[bis(prop-2-ynyl)sulfamoyl]-1,3,4-thiadiazol-2-yl]-3-methylurea Chemical compound CNC(NC1=NN=C(S1)S(=O)(=O)N(CC#C)CC#C)=O BDROSDXBVFYBBA-UHFFFAOYSA-N 0.000 claims 1
- GKXIVKJMYWVKGQ-UHFFFAOYSA-N 1-methyl-3-[5-(methylsulfamoyl)-1,3,4-thiadiazol-2-yl]urea Chemical compound CNC(=O)NC=1SC(=NN1)S(NC)(=O)=O GKXIVKJMYWVKGQ-UHFFFAOYSA-N 0.000 claims 1
- IDBCOQCPRSZMLI-UHFFFAOYSA-N 1-methyl-3-[5-(prop-2-ynylsulfamoyl)-1,3,4-thiadiazol-2-yl]urea Chemical compound CNC(NC1=NN=C(S1)S(=O)(=O)NCC#C)=O IDBCOQCPRSZMLI-UHFFFAOYSA-N 0.000 claims 1
- PRBSDIXAFZUAST-UHFFFAOYSA-N 1-methyl-3-[5-(propan-2-ylsulfamoyl)-1,3,4-thiadiazol-2-yl]urea Chemical compound CNC(NC1=NN=C(S1)S(=O)(=O)NC(C)C)=O PRBSDIXAFZUAST-UHFFFAOYSA-N 0.000 claims 1
- KHVUNHPCUIHPTL-UHFFFAOYSA-N 1-methyl-3-[5-(propylsulfamoyl)-1,3,4-thiadiazol-2-yl]urea Chemical compound CNC(NC1=NN=C(S1)S(=O)(=O)NCCC)=O KHVUNHPCUIHPTL-UHFFFAOYSA-N 0.000 claims 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
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- 125000000623 heterocyclic group Chemical group 0.000 claims 1
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- 239000010871 livestock manure Substances 0.000 description 1
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- IGSSJHNGOQIGBF-UHFFFAOYSA-N n-methyl-n-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide Chemical class CC(=O)N(C)C1=NN=C(S(N)(=O)=O)S1 IGSSJHNGOQIGBF-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920006327 polystyrene foam Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010792 warming Methods 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/119,417 US4021225A (en) | 1971-02-26 | 1971-02-26 | Combating unwanted vegetation with 1,3,4-thiadiazole-2-sulfonamides |
| US00177178A US3824247A (en) | 1971-02-26 | 1971-09-01 | 2-(1,3,3-trimethylureido)-1,3,4-thiadiazole-5-n,n-dimethylsulfonamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2209010A1 true DE2209010A1 (de) | 1972-08-31 |
Family
ID=26817318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722209010 Ceased DE2209010A1 (de) | 1971-02-26 | 1972-02-25 | Unkrautbekämpfungsmittel und Verfahren zur Herstellung derselben |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3824247A (OSRAM) |
| BE (1) | BE779943A (OSRAM) |
| CA (1) | CA1151179A (OSRAM) |
| DE (1) | DE2209010A1 (OSRAM) |
| FR (2) | FR2126419B1 (OSRAM) |
| GB (1) | GB1390272A (OSRAM) |
| NL (1) | NL7202523A (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3932437A (en) * | 1971-09-01 | 1976-01-13 | Gulf Research & Development Company | Multistep synthesis for certain 1,3,4-thiadiazoles and intermediate |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4049670A (en) * | 1968-12-23 | 1977-09-20 | Bayer Aktiengesellschaft | N-(2-Ethylsulfonyl-1,3,4-thiadiazol-5-yl)-N-methyl-N'-methylurea |
| US4028090A (en) * | 1974-10-15 | 1977-06-07 | Eli Lilly And Company | Herbicidal use of 5-cyanoalkyl-1,3,4-thiadiazol-2-ylureas |
| US4165229A (en) * | 1976-05-06 | 1979-08-21 | Eli Lilly And Company | Herbicidal method |
| US4097263A (en) * | 1976-11-22 | 1978-06-27 | Gulf Oil Corporation | 5-Acylamino-1,3,4-thiadiazole-2-sulfonamides and use as herbicides |
| US4187098A (en) * | 1978-11-24 | 1980-02-05 | Gulf Oil Corporation | Selectively herbicidal N-(5-substituted-2-thiadiazolyl)-thiocarboxamides |
| US4562260A (en) * | 1984-07-03 | 1985-12-31 | Union Carbide Corporation | Preparation of 1,3,4-thiadiazole-5-sulfonamides |
-
1971
- 1971-09-01 US US00177178A patent/US3824247A/en not_active Expired - Lifetime
-
1972
- 1972-02-15 GB GB688372A patent/GB1390272A/en not_active Expired
- 1972-02-17 CA CA000134958A patent/CA1151179A/en not_active Expired
- 1972-02-25 FR FR727206478A patent/FR2126419B1/fr not_active Expired
- 1972-02-25 NL NL7202523A patent/NL7202523A/xx not_active Application Discontinuation
- 1972-02-25 DE DE19722209010 patent/DE2209010A1/de not_active Ceased
- 1972-02-28 BE BE779943A patent/BE779943A/xx not_active IP Right Cessation
- 1972-11-06 FR FR7239124A patent/FR2170376A5/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3932437A (en) * | 1971-09-01 | 1976-01-13 | Gulf Research & Development Company | Multistep synthesis for certain 1,3,4-thiadiazoles and intermediate |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2126419B1 (OSRAM) | 1973-08-10 |
| BE779943A (fr) | 1972-06-16 |
| GB1390272A (en) | 1975-04-09 |
| FR2126419A1 (OSRAM) | 1972-10-06 |
| NL7202523A (OSRAM) | 1972-08-29 |
| US3824247A (en) | 1974-07-16 |
| FR2170376A5 (OSRAM) | 1973-09-14 |
| CA1151179A (en) | 1983-08-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8131 | Rejection |