CH617932A5 - Process for the preparation of novel 1-thiadiazolyl-5-acylimidazolidinones and their use in herbicides. - Google Patents
Process for the preparation of novel 1-thiadiazolyl-5-acylimidazolidinones and their use in herbicides. Download PDFInfo
- Publication number
- CH617932A5 CH617932A5 CH1436575A CH1436575A CH617932A5 CH 617932 A5 CH617932 A5 CH 617932A5 CH 1436575 A CH1436575 A CH 1436575A CH 1436575 A CH1436575 A CH 1436575A CH 617932 A5 CH617932 A5 CH 617932A5
- Authority
- CH
- Switzerland
- Prior art keywords
- thiadiazol
- methyl
- imidazolidin
- alkyl
- haloalkyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 11
- 239000004009 herbicide Substances 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 49
- 241000196324 Embryophyta Species 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 125000001188 haloalkyl group Chemical group 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 150000008065 acid anhydrides Chemical class 0.000 claims description 7
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
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- 241000282994 Cervidae Species 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- -1 lower bromoalkyl Chemical group 0.000 description 41
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 23
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- 230000002363 herbicidal effect Effects 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
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- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 12
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 2
- FUKOTTQGWQVMQB-UHFFFAOYSA-N (2-bromoacetyl) 2-bromoacetate Chemical compound BrCC(=O)OC(=O)CBr FUKOTTQGWQVMQB-UHFFFAOYSA-N 0.000 description 1
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- PEHFQQWAINXOQG-UHFFFAOYSA-N (2-methoxyacetyl) 2-methoxyacetate Chemical compound COCC(=O)OC(=O)COC PEHFQQWAINXOQG-UHFFFAOYSA-N 0.000 description 1
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- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- LUEHNHVFDCZTGL-UHFFFAOYSA-N but-2-ynoic acid Chemical compound CC#CC(O)=O LUEHNHVFDCZTGL-UHFFFAOYSA-N 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000012747 synergistic agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- VJDDQSBNUHLBTD-UHFFFAOYSA-N trans-crotonic acid-anhydride Natural products CC=CC(=O)OC(=O)C=CC VJDDQSBNUHLBTD-UHFFFAOYSA-N 0.000 description 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000036642 wellbeing Effects 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)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/567,468 US3997321A (en) | 1975-04-14 | 1975-04-14 | 1-(5-T-butyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-acetyloxy-1,3-imidazolldin-2-one |
| US05/571,466 US4167407A (en) | 1975-04-25 | 1975-04-25 | 1-Thiadiazolyl-5-acylimidazolidinones |
| US05/573,188 US4021439A (en) | 1975-04-30 | 1975-04-30 | 1-(5-Trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-acetyloxy-1,3-imidazolidin-2-one |
| US05/587,006 US4018787A (en) | 1975-06-13 | 1975-06-13 | 1-Thiadiazolyl-5-acylimidazolidinones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH617932A5 true CH617932A5 (en) | 1980-06-30 |
Family
ID=27504864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1436575A CH617932A5 (en) | 1975-04-14 | 1975-11-06 | Process for the preparation of novel 1-thiadiazolyl-5-acylimidazolidinones and their use in herbicides. |
Country Status (19)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1150271A (en) * | 1979-08-10 | 1983-07-19 | Jerome M. Lavanish | 3-¬5-¬1-(alkyloxy or alkylthio)alkyl, alkynyl, alkenyl, or haloalkyl|-1,3,4- thiadiazol-2-yl|-4-hydroxy-1-methyl-2- imidazolidinones |
| DE3246705C2 (de) * | 1981-12-24 | 1986-07-10 | Kureha Kagaku Kogyo K.K., Tokio/Tokyo | Tetrahydrobenzthiazolderivate und diese Verbindungen als wirksamen Bestandteil enthaltende herbizide Mittel |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2303079A1 (de) * | 1973-01-23 | 1974-09-05 | Bayer Ag | Heterocyclisch substituierte 1,3,4-thiadiazolderivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
-
1975
- 1975-10-24 IN IN2053/CAL/75A patent/IN141388B/en unknown
- 1975-10-24 IL IL48358A patent/IL48358A/xx unknown
- 1975-10-31 BE BE161503A patent/BE835155A/xx not_active IP Right Cessation
- 1975-10-31 DE DE19752548847 patent/DE2548847A1/de not_active Ceased
- 1975-11-04 YU YU02781/75A patent/YU39078B/xx unknown
- 1975-11-04 CA CA238,947A patent/CA1060022A/en not_active Expired
- 1975-11-06 CH CH1436575A patent/CH617932A5/de not_active IP Right Cessation
- 1975-11-14 DK DK514675A patent/DK144419C/da not_active IP Right Cessation
- 1975-11-17 NO NO753861A patent/NO753861L/no unknown
- 1975-11-19 ES ES442805A patent/ES442805A1/es not_active Expired
- 1975-11-19 AT AT880375A patent/AT347452B/de not_active IP Right Cessation
- 1975-11-28 NL NL7513915A patent/NL7513915A/xx not_active Application Discontinuation
-
1976
- 1976-01-07 IT IT47549/76A patent/IT1053288B/it active
- 1976-01-12 SU SU762310854A patent/SU588904A3/ru active
- 1976-02-05 FR FR7603202A patent/FR2307811A1/fr active Granted
- 1976-02-16 JP JP1570676A patent/JPS52100472A/ja active Granted
- 1976-02-17 SE SE7601766A patent/SE418500B/xx unknown
- 1976-02-26 BR BR7601233A patent/BR7601233A/pt unknown
- 1976-04-14 GB GB15163/76A patent/GB1545827A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT1053288B (it) | 1981-08-31 |
| BR7601233A (pt) | 1976-10-05 |
| YU39078B (en) | 1984-04-30 |
| AT347452B (de) | 1978-12-27 |
| JPS613789B2 (enrdf_load_stackoverflow) | 1986-02-04 |
| YU278175A (en) | 1982-05-31 |
| NL7513915A (nl) | 1976-10-18 |
| SU588904A3 (ru) | 1978-01-15 |
| JPS52100472A (en) | 1977-08-23 |
| AU8574975A (en) | 1977-04-21 |
| SE418500B (sv) | 1981-06-09 |
| IL48358A0 (en) | 1975-12-31 |
| GB1545827A (en) | 1979-05-16 |
| SE7601766L (sv) | 1976-10-15 |
| FR2307811B1 (enrdf_load_stackoverflow) | 1980-06-27 |
| FR2307811A1 (fr) | 1976-11-12 |
| NO753861L (enrdf_load_stackoverflow) | 1976-10-15 |
| DK144419B (da) | 1982-03-08 |
| IL48358A (en) | 1979-03-12 |
| DK514675A (da) | 1976-10-15 |
| ES442805A1 (es) | 1977-10-01 |
| CA1060022A (en) | 1979-08-07 |
| ATA880375A (de) | 1978-05-15 |
| BE835155A (fr) | 1976-02-16 |
| IN141388B (enrdf_load_stackoverflow) | 1977-02-19 |
| DK144419C (da) | 1982-08-09 |
| DE2548847A1 (de) | 1976-10-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |