DE2500868A1 - Thiadiazolylimidazolidinone - Google Patents
ThiadiazolylimidazolidinoneInfo
- Publication number
- DE2500868A1 DE2500868A1 DE19752500868 DE2500868A DE2500868A1 DE 2500868 A1 DE2500868 A1 DE 2500868A1 DE 19752500868 DE19752500868 DE 19752500868 DE 2500868 A DE2500868 A DE 2500868A DE 2500868 A1 DE2500868 A1 DE 2500868A1
- Authority
- DE
- Germany
- Prior art keywords
- thiadiazol
- hydroxy
- methyl
- imidazolidin
- namely
- 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
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- 239000000203 mixture Substances 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 40
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- 230000002363 herbicidal effect Effects 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 230000006735 deficit Effects 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 230000012010 growth Effects 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 231100000331 toxic Toxicity 0.000 claims description 4
- 230000002588 toxic effect Effects 0.000 claims description 4
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- 241000207890 Ipomoea purpurea Species 0.000 claims description 3
- 235000011999 Panicum crusgalli Nutrition 0.000 claims description 3
- 240000002439 Sorghum halepense Species 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
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- 238000002474 experimental method Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
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- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 56
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- 238000002360 preparation method Methods 0.000 description 23
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000012948 isocyanate Substances 0.000 description 10
- 150000002513 isocyanates Chemical class 0.000 description 8
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- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
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- KZMQZFPRPILIHO-UHFFFAOYSA-N 2-(methylamino)acetaldehyde Chemical compound CNCC=O KZMQZFPRPILIHO-UHFFFAOYSA-N 0.000 description 5
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- 206010061217 Infestation Diseases 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
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- 238000002844 melting Methods 0.000 description 4
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- JUPUBWHBHDEZIX-UHFFFAOYSA-N 2-cyclopropyl-5-isocyanato-1,3,4-thiadiazole Chemical compound S1C(N=C=O)=NN=C1C1CC1 JUPUBWHBHDEZIX-UHFFFAOYSA-N 0.000 description 3
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 3
- YUFFSWGQGVEMMI-JLNKQSITSA-N (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O YUFFSWGQGVEMMI-JLNKQSITSA-N 0.000 description 2
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 description 2
- XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 description 2
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 2
- FGXDZZZMZSWJST-UHFFFAOYSA-N 2-cycloheptyl-5-isocyanato-1,3,4-thiadiazole Chemical compound S1C(N=C=O)=NN=C1C1CCCCCC1 FGXDZZZMZSWJST-UHFFFAOYSA-N 0.000 description 2
- IMTQYYYFKDVUMS-UHFFFAOYSA-N 2-cyclohexyl-5-isocyanato-1,3,4-thiadiazole Chemical compound S1C(N=C=O)=NN=C1C1CCCCC1 IMTQYYYFKDVUMS-UHFFFAOYSA-N 0.000 description 2
- NMFJJZLGSAWEGU-UHFFFAOYSA-N 2-isocyanato-5-(1-methylcyclohexyl)-1,3,4-thiadiazole Chemical compound N=1N=C(N=C=O)SC=1C1(C)CCCCC1 NMFJJZLGSAWEGU-UHFFFAOYSA-N 0.000 description 2
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 2
- VFBWPYIGNOTWEX-UHFFFAOYSA-N 5-(1-methylcyclohexyl)-1,3,4-thiadiazol-2-amine Chemical compound N=1N=C(N)SC=1C1(C)CCCCC1 VFBWPYIGNOTWEX-UHFFFAOYSA-N 0.000 description 2
- ROBHTWLKDVLHNY-UHFFFAOYSA-N 5-cyclobutyl-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1C1CCC1 ROBHTWLKDVLHNY-UHFFFAOYSA-N 0.000 description 2
- BLBDGPFJLDEFFL-UHFFFAOYSA-N 5-cyclohexyl-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1C1CCCCC1 BLBDGPFJLDEFFL-UHFFFAOYSA-N 0.000 description 2
- MGSBORAJOCQFOK-UHFFFAOYSA-N 5-cyclopentyl-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1C1CCCC1 MGSBORAJOCQFOK-UHFFFAOYSA-N 0.000 description 2
- AVLUMBXGKFNNAS-UHFFFAOYSA-N 5-cyclopropyl-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1C1CC1 AVLUMBXGKFNNAS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 241000132536 Cirsium Species 0.000 description 2
- 244000152970 Digitaria sanguinalis Species 0.000 description 2
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PNRAZZZISDRWMV-UHFFFAOYSA-N Terbucarb Chemical compound CNC(=O)OC1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C PNRAZZZISDRWMV-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
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- JEZZOKXIXNSKQD-UHFFFAOYSA-N 1,3-bis(4-nitrophenyl)urea Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1 JEZZOKXIXNSKQD-UHFFFAOYSA-N 0.000 description 1
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- UYGUFXUBSNDUFA-UHFFFAOYSA-N 2,3,5,6-tetrachlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl UYGUFXUBSNDUFA-UHFFFAOYSA-N 0.000 description 1
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- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 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
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43226974A | 1974-01-10 | 1974-01-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2500868A1 true DE2500868A1 (de) | 1975-07-17 |
Family
ID=23715445
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752500868 Ceased DE2500868A1 (de) | 1974-01-10 | 1975-01-10 | Thiadiazolylimidazolidinone |
Country Status (10)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4028375A (en) * | 1974-08-05 | 1977-06-07 | Velsicol Chemical Corporation | Thiadiazolylimidazolidinones |
| JP2003220983A (ja) | 2002-01-31 | 2003-08-05 | Komatsu Ltd | ロータリブシュ式履帯 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA741626B (en) * | 1973-06-29 | 1975-02-26 | Velsicol Chemical Corp | New thiadiazolylimidazolidinones |
-
1974
- 1974-11-25 CA CA214,588A patent/CA1042898A/en not_active Expired
- 1974-11-28 IL IL46149A patent/IL46149A/xx unknown
- 1974-12-23 JP JP49147912A patent/JPS5852964B2/ja not_active Expired
-
1975
- 1975-01-02 NL NL7500004A patent/NL7500004A/xx not_active Application Discontinuation
- 1975-01-08 FR FR7500441A patent/FR2257592B1/fr not_active Expired
- 1975-01-08 BR BR119/75A patent/BR7500119A/pt unknown
- 1975-01-09 GB GB85975A patent/GB1456342A/en not_active Expired
- 1975-01-10 DE DE19752500868 patent/DE2500868A1/de not_active Ceased
- 1975-01-10 BE BE152288A patent/BE824282A/xx not_active IP Right Cessation
- 1975-01-10 CH CH25975A patent/CH609205A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA1042898A (en) | 1978-11-21 |
| FR2257592B1 (enrdf_load_stackoverflow) | 1979-03-09 |
| GB1456342A (en) | 1976-11-24 |
| IL46149A (en) | 1978-07-31 |
| BE824282A (fr) | 1975-05-02 |
| AU7657974A (en) | 1976-06-24 |
| BR7500119A (pt) | 1975-11-04 |
| CH609205A5 (en) | 1979-02-28 |
| NL7500004A (nl) | 1975-07-14 |
| JPS50100238A (enrdf_load_stackoverflow) | 1975-08-08 |
| JPS5852964B2 (ja) | 1983-11-26 |
| FR2257592A1 (enrdf_load_stackoverflow) | 1975-08-08 |
| IL46149A0 (en) | 1975-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |