CA1072560A - 5-(hetero-ring sulfamoyl)-1,3,4-thiadiazol-2-ylureas - Google Patents
5-(hetero-ring sulfamoyl)-1,3,4-thiadiazol-2-ylureasInfo
- Publication number
- CA1072560A CA1072560A CA256,618A CA256618A CA1072560A CA 1072560 A CA1072560 A CA 1072560A CA 256618 A CA256618 A CA 256618A CA 1072560 A CA1072560 A CA 1072560A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- thiadiazol
- triyl
- urea
- sulfamoyl
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 241000196324 Embryophyta Species 0.000 claims abstract description 40
- 239000004202 carbamide Substances 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 239000011593 sulfur Substances 0.000 claims abstract description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 63
- -1 1,1,4-butanetriyl Chemical group 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- DQCVPSBQJTWRAO-UHFFFAOYSA-N 1,3-dimethyl-1-[5-[methyl(pyridin-3-ylmethyl)sulfamoyl]-1,3,4-thiadiazol-2-yl]urea Chemical compound S1C(N(C)C(=O)NC)=NN=C1S(=O)(=O)N(C)CC1=CC=CN=C1 DQCVPSBQJTWRAO-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- MUBRTDVZPRSQOK-UHFFFAOYSA-N 1-[5-[furan-2-ylmethyl(methyl)sulfamoyl]-1,3,4-thiadiazol-2-yl]-1,3-dimethylurea Chemical compound S1C(N(C)C(=O)NC)=NN=C1S(=O)(=O)N(C)CC1=CC=CO1 MUBRTDVZPRSQOK-UHFFFAOYSA-N 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 43
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract description 16
- 230000002363 herbicidal effect Effects 0.000 abstract description 10
- 239000004009 herbicide Substances 0.000 abstract description 10
- 125000000217 alkyl group Chemical group 0.000 abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 abstract description 5
- OXBOABAOQWBSIV-UHFFFAOYSA-N [N]S(N)(=O)=O Chemical compound [N]S(N)(=O)=O OXBOABAOQWBSIV-UHFFFAOYSA-N 0.000 abstract description 4
- 239000004480 active ingredient Substances 0.000 abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract description 3
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- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
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- 238000012360 testing method Methods 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 16
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
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- 238000000921 elemental analysis Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 244000152970 Digitaria sanguinalis Species 0.000 description 6
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
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- VHXDHGALQPVNKI-UHFFFAOYSA-N thiadiazol-4-ylurea Chemical class NC(=O)NC1=CSN=N1 VHXDHGALQPVNKI-UHFFFAOYSA-N 0.000 description 6
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- 239000008188 pellet Substances 0.000 description 5
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- 235000011167 hydrochloric acid Nutrition 0.000 description 4
- 229960000443 hydrochloric acid Drugs 0.000 description 4
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 4
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- 241000894007 species Species 0.000 description 4
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- WINUKGWOUSNWME-UHFFFAOYSA-N 5-(methylamino)-1,3,4-thiadiazole-2-sulfonyl chloride Chemical compound CNC1=NN=C(S(Cl)(=O)=O)S1 WINUKGWOUSNWME-UHFFFAOYSA-N 0.000 description 3
- 240000006995 Abutilon theophrasti Species 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- 229910021641 deionized water Inorganic materials 0.000 description 3
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- 239000003337 fertilizer Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
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- AOKMOIBHYHWEMV-UHFFFAOYSA-N n-methyl-5-(methylamino)-n-(pyridin-3-ylmethyl)-1,3,4-thiadiazole-2-sulfonamide Chemical compound S1C(NC)=NN=C1S(=O)(=O)N(C)CC1=CC=CN=C1 AOKMOIBHYHWEMV-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
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- 150000004867 thiadiazoles Chemical group 0.000 description 3
- 241000335053 Beta vulgaris Species 0.000 description 2
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- UBQQJXNQWLWWID-UHFFFAOYSA-N n-(furan-2-ylmethyl)-n-methyl-5-(methylamino)-1,3,4-thiadiazole-2-sulfonamide Chemical compound S1C(NC)=NN=C1S(=O)(=O)N(C)CC1=CC=CO1 UBQQJXNQWLWWID-UHFFFAOYSA-N 0.000 description 2
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- VJUDVVHGQMPPEI-UHFFFAOYSA-N n-methyl-1-(oxolan-2-yl)methanamine Chemical compound CNCC1CCCO1 VJUDVVHGQMPPEI-UHFFFAOYSA-N 0.000 description 1
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- LCUHGDGTJNEZBG-UHFFFAOYSA-N n-methyl-5-(methylamino)-n-(oxolan-2-ylmethyl)-1,3,4-thiadiazole-2-sulfonamide Chemical compound S1C(NC)=NN=C1S(=O)(=O)N(C)CC1OCCC1 LCUHGDGTJNEZBG-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 1
- 235000002252 panizo Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- ZQZJKHIIQFPZCS-UHFFFAOYSA-N propylurea Chemical compound CCCNC(N)=O ZQZJKHIIQFPZCS-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000004016 soil organic matter Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/607,850 US3990881A (en) | 1975-08-25 | 1975-08-25 | 5-(Hetero-ring sulfamoyl)-1,3,4-thiadiazol-2-ylureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1072560A true CA1072560A (en) | 1980-02-26 |
Family
ID=24433980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA256,618A Expired CA1072560A (en) | 1975-08-25 | 1976-07-08 | 5-(hetero-ring sulfamoyl)-1,3,4-thiadiazol-2-ylureas |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3990881A (OSRAM) |
| JP (1) | JPS5227770A (OSRAM) |
| BE (1) | BE845443A (OSRAM) |
| BR (1) | BR7605536A (OSRAM) |
| CA (1) | CA1072560A (OSRAM) |
| CH (1) | CH619114A5 (OSRAM) |
| DE (1) | DE2638319A1 (OSRAM) |
| FR (1) | FR2322147A1 (OSRAM) |
| GB (1) | GB1555353A (OSRAM) |
| IE (1) | IE43250B1 (OSRAM) |
| IL (1) | IL49957A (OSRAM) |
| IT (1) | IT1076937B (OSRAM) |
| NL (1) | NL7609197A (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4255182A (en) * | 1980-03-10 | 1981-03-10 | Velsicol Chemical Corporation | Aminosulfonylthiadiazolylureas |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670925B2 (de) * | 1967-09-19 | 1977-03-10 | Bayer Ag, 5090 Leverkusen | 1,3,4-thiadiazolylharnstoffe |
| CH488723A (de) * | 1967-12-27 | 1970-04-15 | Agripat Sa | Verfahren zur Herstellung von Thiadiazolyl-harnstoffen |
| GB1290223A (OSRAM) * | 1969-04-21 | 1972-09-20 | ||
| CH535540A (de) * | 1970-04-23 | 1973-04-15 | Agripat Sa | Herbizides Mittel |
| NL7106557A (OSRAM) * | 1970-06-15 | 1971-12-17 | ||
| US3726892A (en) * | 1970-10-02 | 1973-04-10 | Air Prod & Chem | Certain 5-sulfamoyl-1,3,4-thiadiazol-2-ylureas |
-
1975
- 1975-08-25 US US05/607,850 patent/US3990881A/en not_active Expired - Lifetime
-
1976
- 1976-06-29 IE IE1415/76A patent/IE43250B1/en unknown
- 1976-07-01 IL IL49957A patent/IL49957A/xx unknown
- 1976-07-08 CA CA256,618A patent/CA1072560A/en not_active Expired
- 1976-08-19 GB GB34553/76A patent/GB1555353A/en not_active Expired
- 1976-08-19 NL NL7609197A patent/NL7609197A/xx not_active Application Discontinuation
- 1976-08-24 FR FR7625571A patent/FR2322147A1/fr active Granted
- 1976-08-24 IT IT26501/76A patent/IT1076937B/it active
- 1976-08-24 BE BE1007573A patent/BE845443A/xx not_active IP Right Cessation
- 1976-08-24 BR BR7605536A patent/BR7605536A/pt unknown
- 1976-08-25 JP JP51103072A patent/JPS5227770A/ja active Pending
- 1976-08-25 DE DE19762638319 patent/DE2638319A1/de not_active Ceased
- 1976-08-25 CH CH1079076A patent/CH619114A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IE43250B1 (en) | 1981-01-14 |
| IE43250L (en) | 1977-02-25 |
| IL49957A (en) | 1979-03-12 |
| NL7609197A (nl) | 1977-03-01 |
| IT1076937B (it) | 1985-04-27 |
| BR7605536A (pt) | 1977-08-09 |
| FR2322147A1 (fr) | 1977-03-25 |
| BE845443A (fr) | 1977-02-24 |
| CH619114A5 (OSRAM) | 1980-09-15 |
| GB1555353A (en) | 1979-11-07 |
| JPS5227770A (en) | 1977-03-02 |
| DE2638319A1 (de) | 1977-03-10 |
| FR2322147B1 (OSRAM) | 1978-05-05 |
| IL49957A0 (en) | 1976-09-30 |
| US3990881A (en) | 1976-11-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |