CA2871315C - Crystalline form a of 1,5-dimethyl-6-thioxo-3-(2,2,7-trifluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2h-benzo[b][1,4]oxazin-6-yl)-1,3,5-triazinane-2,4-dione - Google Patents
Crystalline form a of 1,5-dimethyl-6-thioxo-3-(2,2,7-trifluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2h-benzo[b][1,4]oxazin-6-yl)-1,3,5-triazinane-2,4-dione Download PDFInfo
- Publication number
- CA2871315C CA2871315C CA2871315A CA2871315A CA2871315C CA 2871315 C CA2871315 C CA 2871315C CA 2871315 A CA2871315 A CA 2871315A CA 2871315 A CA2871315 A CA 2871315A CA 2871315 C CA2871315 C CA 2871315C
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- Canada
- Prior art keywords
- triazinane
- thioxo
- trifluoro
- benzo
- dione
- 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.)
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- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000011356 non-aqueous organic solvent Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000010499 rapseed oil Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000013526 red clover Nutrition 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000029219 regulation of pH Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000000373 single-crystal X-ray diffraction data Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000008259 solid foam Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- UJMBCXLDXJUMFB-GLCFPVLVSA-K tartrazine Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-GLCFPVLVSA-K 0.000 description 1
- 235000012756 tartrazine Nutrition 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- 238000010626 work up procedure Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
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- 239000005019 zein Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Toxicology (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261651602P | 2012-05-25 | 2012-05-25 | |
| US61/651,602 | 2012-05-25 | ||
| EP12169638 | 2012-05-25 | ||
| EP12169638.9 | 2012-05-25 | ||
| PCT/EP2013/060028 WO2013174693A1 (en) | 2012-05-25 | 2013-05-15 | Crystalline form a of 1,5-dimethyl-6-thioxo-3-(2,2,7-trifluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2h-benzo[b][1,4]oxazin-6-yl)-1,3,5-triazinane-2,4-dione |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2871315A1 CA2871315A1 (en) | 2013-11-28 |
| CA2871315C true CA2871315C (en) | 2020-11-03 |
Family
ID=49623178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2871315A Active CA2871315C (en) | 2012-05-25 | 2013-05-15 | Crystalline form a of 1,5-dimethyl-6-thioxo-3-(2,2,7-trifluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2h-benzo[b][1,4]oxazin-6-yl)-1,3,5-triazinane-2,4-dione |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US9353095B2 (enExample) |
| EP (1) | EP2855461A1 (enExample) |
| JP (1) | JP2015518840A (enExample) |
| KR (1) | KR20150023487A (enExample) |
| CN (1) | CN104334549B (enExample) |
| AR (1) | AR093212A1 (enExample) |
| AU (1) | AU2013265471B2 (enExample) |
| BR (1) | BR112014028723A2 (enExample) |
| CA (1) | CA2871315C (enExample) |
| CO (1) | CO7160073A2 (enExample) |
| CR (1) | CR20140546A (enExample) |
| EA (1) | EA027898B1 (enExample) |
| IL (1) | IL235695A0 (enExample) |
| IN (1) | IN2014MN02342A (enExample) |
| MX (1) | MX2014014395A (enExample) |
| UA (1) | UA117100C2 (enExample) |
| WO (1) | WO2013174693A1 (enExample) |
| ZA (1) | ZA201409460B (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9340536B2 (en) | 2012-06-15 | 2016-05-17 | Basf Se | Multicomponent crystals comprising dasatinib and selected co-crystal formers |
| US9221789B2 (en) | 2012-06-22 | 2015-12-29 | Basf Se | Multicomponent crystals comprising imatinib mesilate and selected co-crystal formers |
| BR112015008552A2 (pt) | 2012-10-19 | 2017-07-04 | Basf Se | material cristalino, composição farmacêutica, e, processo para a preparação de um material cristalino |
| EP2868196A1 (en) * | 2013-11-05 | 2015-05-06 | Basf Se | Herbicidal compositions |
| AU2014350467B2 (en) * | 2013-11-14 | 2018-02-01 | Basf Se | Composition of 1,5-dimethyl-6-thioxo-3-(2,2,7-trifluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-1,3,5-triazinane-2,4-dione |
| WO2015092706A1 (en) | 2013-12-18 | 2015-06-25 | BASF Agro B.V. | Plants having increased tolerance to herbicides |
| CN106232604A (zh) | 2014-04-17 | 2016-12-14 | 巴斯夫欧洲公司 | 具有除草活性的取代吡啶化合物 |
| EP3112016A1 (en) | 2015-07-02 | 2017-01-04 | Basf Se | Microcapsules containing benzoxazinones |
| WO2017202774A1 (en) | 2016-05-24 | 2017-11-30 | Basf Se | Method for controlling ppo resistant weeds |
| WO2019158378A1 (en) | 2018-02-16 | 2019-08-22 | Basf Se | Herbicidal mixtures |
| US10772329B2 (en) | 2018-12-26 | 2020-09-15 | Sumitomo Chemical Company, Limited | Method of controlling weeds |
| WO2024012913A1 (en) | 2022-07-13 | 2024-01-18 | BASF Agro B.V. | Herbicidal eode formulation comprising several active ingredients |
| WO2025031864A1 (en) | 2023-08-04 | 2025-02-13 | Basf Se | Herbicidal compositions comprising trifludimoxazin |
| WO2025098807A1 (en) | 2023-11-07 | 2025-05-15 | Basf Se | Herbicidal compositions comprising glyphosate |
| WO2025114125A1 (en) | 2023-12-01 | 2025-06-05 | Basf Se | Herbicidal compositions comprising glufosinate |
| WO2025124944A1 (en) | 2023-12-12 | 2025-06-19 | Basf Se | Herbicidal compositions comprising 2,4-d |
| WO2025172125A1 (en) | 2024-02-16 | 2025-08-21 | Basf Se | Herbicidal compositions comprising pyroxasulfone |
| WO2025172127A1 (en) | 2024-02-16 | 2025-08-21 | Basf Se | Herbicidal compositions comprising imazethapyr |
| WO2025176575A1 (en) | 2024-02-23 | 2025-08-28 | Basf Se | Herbicidal compositions comprising dimethenamid |
| WO2025180968A1 (en) | 2024-02-27 | 2025-09-04 | Basf Se | Herbicidal compositions comprising mesotrione |
| WO2025209887A1 (en) | 2024-04-05 | 2025-10-09 | Basf Se | Herbicidal compositions comprising topramezone |
| WO2025228721A1 (en) | 2024-04-30 | 2025-11-06 | Basf Se | Herbicidal compositions comprising isoxaflutole |
| WO2025237738A1 (en) | 2024-05-16 | 2025-11-20 | Basf Se | Herbicidal compositions comprising clethodim |
| WO2025237741A1 (en) | 2024-05-16 | 2025-11-20 | Basf Se | Herbicidal compositions comprising diclosulam |
| WO2025237737A1 (en) | 2024-05-16 | 2025-11-20 | Basf Se | Herbicidal compositions comprising acetochlor |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0419075D0 (en) * | 2004-08-26 | 2004-09-29 | Syngenta Participations Ag | Process |
| PL2346326T3 (pl) * | 2008-10-14 | 2014-08-29 | Basf Se | Krystaliczne kompleksy pendimetaliny i metazachloru |
| EP2443102B1 (en) * | 2009-06-19 | 2013-04-17 | Basf Se | Herbicidal benzoxazinones |
| US8765640B2 (en) * | 2009-11-04 | 2014-07-01 | Nissan Chemical Industries, Ltd. | Crystal forms of sulfonylurea compound and method for producing the same |
| US8481723B2 (en) * | 2009-11-13 | 2013-07-09 | Basf Se | 3-(3,4-dihydro-2H-benzo [1,4]oxazin-6-yl)-1H-Pyrimidin-2,4-dione compounds as herbicides |
| WO2011161131A1 (en) * | 2010-06-25 | 2011-12-29 | Basf Se | Herbicidal mixtures |
-
2013
- 2013-05-15 BR BR112014028723A patent/BR112014028723A2/pt not_active Application Discontinuation
- 2013-05-15 UA UAA201413766A patent/UA117100C2/uk unknown
- 2013-05-15 AU AU2013265471A patent/AU2013265471B2/en active Active
- 2013-05-15 EP EP13723123.9A patent/EP2855461A1/en not_active Ceased
- 2013-05-15 WO PCT/EP2013/060028 patent/WO2013174693A1/en not_active Ceased
- 2013-05-15 KR KR20147036346A patent/KR20150023487A/ko not_active Ceased
- 2013-05-15 CN CN201380027344.5A patent/CN104334549B/zh active Active
- 2013-05-15 IN IN2342MUN2014 patent/IN2014MN02342A/en unknown
- 2013-05-15 EA EA201401310A patent/EA027898B1/ru not_active IP Right Cessation
- 2013-05-15 MX MX2014014395A patent/MX2014014395A/es unknown
- 2013-05-15 US US14/402,518 patent/US9353095B2/en active Active
- 2013-05-15 JP JP2015513094A patent/JP2015518840A/ja active Pending
- 2013-05-15 CA CA2871315A patent/CA2871315C/en active Active
- 2013-05-24 AR ARP130101830A patent/AR093212A1/es not_active Application Discontinuation
-
2014
- 2014-11-13 IL IL235695A patent/IL235695A0/en unknown
- 2014-12-01 CR CR20140546A patent/CR20140546A/es unknown
- 2014-12-18 CO CO14278794A patent/CO7160073A2/es unknown
- 2014-12-22 ZA ZA2014/09460A patent/ZA201409460B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA201409460B (en) | 2016-10-26 |
| CA2871315A1 (en) | 2013-11-28 |
| BR112014028723A2 (pt) | 2017-06-27 |
| EA201401310A1 (ru) | 2015-05-29 |
| IN2014MN02342A (enExample) | 2015-08-14 |
| CR20140546A (es) | 2015-03-06 |
| CN104334549B (zh) | 2017-03-22 |
| US20150099631A1 (en) | 2015-04-09 |
| EP2855461A1 (en) | 2015-04-08 |
| EA027898B1 (ru) | 2017-09-29 |
| UA117100C2 (uk) | 2018-06-25 |
| WO2013174693A1 (en) | 2013-11-28 |
| KR20150023487A (ko) | 2015-03-05 |
| CO7160073A2 (es) | 2015-01-15 |
| AU2013265471A1 (en) | 2014-12-04 |
| IL235695A0 (en) | 2015-02-01 |
| AR093212A1 (es) | 2015-05-27 |
| CN104334549A (zh) | 2015-02-04 |
| AU2013265471B2 (en) | 2017-03-02 |
| US9353095B2 (en) | 2016-05-31 |
| JP2015518840A (ja) | 2015-07-06 |
| MX2014014395A (es) | 2015-08-12 |
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| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20180511 |