TW200811092A - Novel crystalline modifications of 3-chloro-N2-[(1S)-1-methyl-2-(methylsulphonyl)ethyl]-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}phthalamide - Google Patents
Novel crystalline modifications of 3-chloro-N2-[(1S)-1-methyl-2-(methylsulphonyl)ethyl]-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}phthalamide Download PDFInfo
- Publication number
- TW200811092A TW200811092A TW96110660A TW96110660A TW200811092A TW 200811092 A TW200811092 A TW 200811092A TW 96110660 A TW96110660 A TW 96110660A TW 96110660 A TW96110660 A TW 96110660A TW 200811092 A TW200811092 A TW 200811092A
- Authority
- TW
- Taiwan
- Prior art keywords
- ethyl
- methyl
- phenyl
- decylamine
- tetrafluoro
- Prior art date
Links
- 238000012986 modification Methods 0.000 title claims abstract description 39
- 230000004048 modification Effects 0.000 title claims abstract description 39
- QZMQZUFFUNIGOE-LBPRGKRZSA-N 3-chloro-1-n-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-methylphenyl]-2-n-[(2s)-1-methylsulfonylpropan-2-yl]benzene-1,2-dicarboxamide Chemical compound CS(=O)(=O)C[C@H](C)NC(=O)C1=C(Cl)C=CC=C1C(=O)NC1=CC=C(C(F)(C(F)(F)F)C(F)(F)F)C=C1C QZMQZUFFUNIGOE-LBPRGKRZSA-N 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 30
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 59
- 239000013078 crystal Substances 0.000 claims description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 32
- 238000001228 spectrum Methods 0.000 claims description 23
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000002425 crystallisation Methods 0.000 claims description 13
- 230000008025 crystallization Effects 0.000 claims description 13
- 238000009472 formulation Methods 0.000 claims description 11
- 239000003495 polar organic solvent Substances 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 239000002798 polar solvent Substances 0.000 claims description 5
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 239000012454 non-polar solvent Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 11
- 230000005855 radiation Effects 0.000 claims 9
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 7
- 241000238631 Hexapoda Species 0.000 claims 6
- -1 phenyl decylamine Chemical compound 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 229910016523 CuKa Inorganic materials 0.000 claims 3
- GVSMQKKMAYLKMM-UHFFFAOYSA-N 3-chloro-1h-indole Chemical compound C1=CC=C2C(Cl)=CNC2=C1 GVSMQKKMAYLKMM-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 230000000749 insecticidal effect Effects 0.000 claims 2
- ZKXGQPQAMRSBOL-UHFFFAOYSA-N 1,2,3-trifluoro-9h-fluorene Chemical compound C12=CC=CC=C2CC2=C1C=C(F)C(F)=C2F ZKXGQPQAMRSBOL-UHFFFAOYSA-N 0.000 claims 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims 1
- 229910002483 Cu Ka Inorganic materials 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 229920000877 Melamine resin Polymers 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 claims 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims 1
- 230000000361 pesticidal effect Effects 0.000 claims 1
- NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical compound NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- 235000021419 vinegar Nutrition 0.000 claims 1
- 239000000052 vinegar Substances 0.000 claims 1
- 239000003905 agrochemical Substances 0.000 abstract description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- 238000001953 recrystallisation Methods 0.000 description 13
- 238000010992 reflux Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 6
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 238000001308 synthesis method Methods 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000011877 solvent mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- NUPSHWCALHZGOV-UHFFFAOYSA-N Decyl acetate Chemical compound CCCCCCCCCCOC(C)=O NUPSHWCALHZGOV-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000001069 Raman spectroscopy Methods 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000011549 crystallization solution Substances 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 238000001144 powder X-ray diffraction data Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE200610014491 DE102006014491A1 (de) | 2006-03-29 | 2006-03-29 | Neue kristalline Modifikationen von3-Chlor-N2-[(1S)-1-methyl-2-(methyl-sulfonyl)ethyl]-N1-{2-methyl-4-[1,2,2,2-tetrafluor-1(trifluormethyl)-ethyl]}phthalamid |
| DE200610031647 DE102006031647A1 (de) | 2006-07-08 | 2006-07-08 | Neue kristalline Modifikationen von 3-Chlor-N2-[(1S)-1-methyl-2-(methyl-sulfonyl)ethyl]-N1-{2-methyl-4[1,2,2,2-tetrafluor-1-(trifluormethyl)-ethyl]phenyl}phthalamid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200811092A true TW200811092A (en) | 2008-03-01 |
Family
ID=38093176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW96110660A TW200811092A (en) | 2006-03-29 | 2007-03-28 | Novel crystalline modifications of 3-chloro-N2-[(1S)-1-methyl-2-(methylsulphonyl)ethyl]-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}phthalamide |
Country Status (3)
| Country | Link |
|---|---|
| AR (1) | AR060135A1 (de) |
| TW (1) | TW200811092A (de) |
| WO (1) | WO2007112844A1 (de) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0921344D0 (en) | 2009-12-04 | 2010-01-20 | Syngenta Participations Ag | Chemical compounds |
| GB0921343D0 (en) | 2009-12-04 | 2010-01-20 | Syngenta Participations Ag | Chemical compounds |
| GB0921346D0 (en) | 2009-12-04 | 2010-01-20 | Syngenta Participations Ag | Chemical compounds |
| EP2531484B1 (de) | 2010-02-03 | 2016-08-17 | Syngenta Participations AG | Insektizidverbindungen |
| MX2012010507A (es) | 2010-03-18 | 2012-10-09 | Syngenta Participations Ag | Compuestos insecticidas. |
| BR112012030473A2 (pt) | 2010-05-31 | 2015-09-29 | Syngenta Participations Ag | pesticidas baseados em derivados pirrolidina espiroheterocíclicos |
| US9023760B2 (en) | 2010-05-31 | 2015-05-05 | Syngenta Participations Ag | 1, 8-diazaspiro [4.5] decane-2, 4-dione derivatives useful as pesticides |
| EP2576554A1 (de) | 2010-05-31 | 2013-04-10 | Syngenta Participations AG | 1, 8 -diazaspiro [4.5]decan- 2, 4 -dion-derivate als pestizide |
| US20130269064A1 (en) | 2010-11-23 | 2013-10-10 | Syngenta Participations Ag | Insecticidal compounds |
| WO2012175474A1 (en) | 2011-06-20 | 2012-12-27 | Syngenta Participations Ag | 1,2,3 triazole pesticides |
| AR087008A1 (es) | 2011-06-22 | 2014-02-05 | Syngenta Participations Ag | Derivados de n-oxi-pirazolo-triazepina-diona |
| PT2785708E (pt) | 2011-11-29 | 2016-06-03 | Syngenta Participations Ag | Derivados de triazinona inseticidas |
| WO2013127768A1 (en) | 2012-03-01 | 2013-09-06 | Syngenta Participations Ag | Pyridine carboxamide pesticides |
| WO2013127780A1 (en) | 2012-03-01 | 2013-09-06 | Syngenta Participations Ag | Chemical compounds |
| EP2647626A1 (de) | 2012-04-03 | 2013-10-09 | Syngenta Participations AG. | 1-Aza-spiro[4.5]dec-3-en- und 1,8-Diaza-spiro[4.5]dec-3-enderivate als Pestizide |
| WO2014023531A1 (en) | 2012-08-07 | 2014-02-13 | Syngenta Participations Ag | Trifluoromethylpyridine carboxamides as pesticides |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ299375B6 (cs) * | 1998-11-30 | 2008-07-09 | Nihon Nohyaku Co., Ltd. | Ftalamidové deriváty nebo jejich soli, zemedelsko-zahradnický insekticid je obsahující a jeho použití |
| JP2006089469A (ja) * | 2004-08-23 | 2006-04-06 | Nippon Nohyaku Co Ltd | 光学活性フタルアミド誘導体及び農園芸用殺虫剤並びにその使用方法 |
| US20080051457A1 (en) * | 2004-08-23 | 2008-02-28 | Hayami Nakao | Optically Active Phthalamide Derivative, Agricultural or Horticultural Insecticide, and Method of Using the Same |
-
2007
- 2007-03-19 WO PCT/EP2007/002388 patent/WO2007112844A1/de not_active Ceased
- 2007-03-26 AR ARP070101246A patent/AR060135A1/es unknown
- 2007-03-28 TW TW96110660A patent/TW200811092A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007112844A1 (de) | 2007-10-11 |
| AR060135A1 (es) | 2008-05-28 |
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