DK174188B1 - Krystallinsk materiale og fremgangsmåde til fremstilling deraf - Google Patents
Krystallinsk materiale og fremgangsmåde til fremstilling deraf Download PDFInfo
- Publication number
- DK174188B1 DK174188B1 DK462583A DK462583A DK174188B1 DK 174188 B1 DK174188 B1 DK 174188B1 DK 462583 A DK462583 A DK 462583A DK 462583 A DK462583 A DK 462583A DK 174188 B1 DK174188 B1 DK 174188B1
- Authority
- DK
- Denmark
- Prior art keywords
- isomer
- cis
- isomers
- chloro
- cyano
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- 239000002178 crystalline material Substances 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title description 4
- 239000013078 crystal Substances 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 14
- 238000002844 melting Methods 0.000 claims description 12
- 230000008018 melting Effects 0.000 claims description 12
- -1 2-Chloro-3,3,3-trifluoroprop-1-en-1-yl Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 7
- 238000001953 recrystallisation Methods 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- WQAZXRGPWRCXCW-UHFFFAOYSA-N 3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-1-[cyano-(3-phenoxyphenyl)methyl]-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C=C(Cl)C(F)(F)F)C1(C(O)=O)C(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 WQAZXRGPWRCXCW-UHFFFAOYSA-N 0.000 claims description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000000862 absorption spectrum Methods 0.000 claims 2
- YDNMYOFECSHWOA-UHFFFAOYSA-N cyano 3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-1-[(3-phenoxyphenyl)methyl]cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(Cl)C(F)(F)F)C1(C(=O)OC#N)CC1=CC=CC(OC=2C=CC=CC=2)=C1 YDNMYOFECSHWOA-UHFFFAOYSA-N 0.000 claims 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 claims 1
- 239000000047 product Substances 0.000 description 42
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000002917 insecticide Substances 0.000 description 4
- 238000010899 nucleation Methods 0.000 description 4
- 230000006911 nucleation Effects 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- WQAZXRGPWRCXCW-UNOMPAQXSA-N 3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-1-[cyano-(3-phenoxyphenyl)methyl]-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1(C(O)=O)C(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 WQAZXRGPWRCXCW-UNOMPAQXSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- AFVLVVWMAFSXCK-VMPITWQZSA-N alpha-cyano-4-hydroxycinnamic acid Chemical group OC(=O)C(\C#N)=C\C1=CC=C(O)C=C1 AFVLVVWMAFSXCK-VMPITWQZSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 150000001942 cyclopropanes Chemical class 0.000 description 1
- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical class CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
Landscapes
- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8228983 | 1982-10-11 | ||
| GB8228983 | 1982-10-11 | ||
| GB838308507A GB8308507D0 (en) | 1983-03-28 | 1983-03-28 | Insecticidal product |
| GB8308507 | 1983-03-28 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK462583D0 DK462583D0 (da) | 1983-10-07 |
| DK462583A DK462583A (da) | 1984-04-12 |
| DK174188B1 true DK174188B1 (da) | 2002-08-26 |
Family
ID=26284087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK462583A DK174188B1 (da) | 1982-10-11 | 1983-10-07 | Krystallinsk materiale og fremgangsmåde til fremstilling deraf |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0106469B1 (https=) |
| JP (1) | JPH0660146B2 (https=) |
| AU (1) | AU555544B2 (https=) |
| CA (1) | CA1212686A (https=) |
| DE (1) | DE3369128D1 (https=) |
| DK (1) | DK174188B1 (https=) |
| ES (1) | ES526409A0 (https=) |
| GB (1) | GB2130199A (https=) |
| GR (1) | GR78644B (https=) |
| HU (1) | HU193185B (https=) |
| IL (1) | IL69774A (https=) |
| NZ (1) | NZ205561A (https=) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0107296B1 (en) * | 1982-10-18 | 1987-07-15 | Imperial Chemical Industries Plc | Insecticidal product and preparation thereof |
| GB8418331D0 (en) * | 1984-07-18 | 1984-08-22 | Ici Plc | Insecticidal ester |
| GB9127355D0 (en) * | 1991-12-24 | 1992-02-19 | Ici Plc | Isomerisation process |
| DE10203688A1 (de) | 2002-01-31 | 2003-08-07 | Bayer Cropscience Ag | Synergistische insektizide Mischungen |
| US6854691B2 (en) * | 2002-02-11 | 2005-02-15 | General Electric Company | Railroad communication system |
| GB0229803D0 (en) * | 2002-12-20 | 2003-01-29 | Syngenta Ltd | Chemical process |
| DE102004001271A1 (de) | 2004-01-08 | 2005-08-04 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
| DE102006008691A1 (de) * | 2006-02-24 | 2007-08-30 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE102007045953B4 (de) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2227951A1 (de) | 2009-01-23 | 2010-09-15 | Bayer CropScience AG | Verwendung von Enaminocarbonylverbindungen zur Bekämpfung von durch Insekten übertragenen Viren |
| US8828906B2 (en) | 2009-03-25 | 2014-09-09 | Bayer Cropscience Ag | Active compound combinations having insecticidal and acaricidal properties |
| DE102009028001A1 (de) | 2009-07-24 | 2011-01-27 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2382865A1 (de) | 2010-04-28 | 2011-11-02 | Bayer CropScience AG | Synergistische Wirkstoffkombinationen |
| EP2446742A1 (de) | 2010-10-28 | 2012-05-02 | Bayer CropScience AG | Insektizide oder akarizide Zusammensetzungen enthaltend Mono- oder Disacchariden als Wirkungsverstärker |
| CN109111373A (zh) * | 2018-10-09 | 2019-01-01 | 南通天泽化工有限公司 | 一种三氟氯氰菊酯的制备方法 |
| WO2022200364A1 (en) | 2021-03-25 | 2022-09-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
| JP2024516912A (ja) | 2021-05-14 | 2024-04-17 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | 昆虫、ダニ目及び線虫有害生物の防除 |
| WO2022268813A1 (en) | 2021-06-24 | 2022-12-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
| WO2022268815A1 (en) | 2021-06-24 | 2022-12-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
| WO2023105064A1 (en) | 2021-12-10 | 2023-06-15 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
| WO2023105065A1 (en) | 2021-12-10 | 2023-06-15 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4183948A (en) * | 1977-01-24 | 1980-01-15 | Imperial Chemical Industries Limited | Halogenated esters |
| GB2000764B (en) * | 1977-03-23 | 1982-04-28 | Ici Ltd | Halogenated esters |
| CA1150301A (en) * | 1979-11-27 | 1983-07-19 | Michael J. Bull | Cyclopropane carboxylic acid ester derivatives |
-
1983
- 1983-08-31 GB GB08323361A patent/GB2130199A/en not_active Withdrawn
- 1983-08-31 EP EP19830305005 patent/EP0106469B1/en not_active Expired
- 1983-08-31 DE DE8383305005T patent/DE3369128D1/de not_active Expired
- 1983-09-08 GR GR72406A patent/GR78644B/el unknown
- 1983-09-12 NZ NZ20556183A patent/NZ205561A/en unknown
- 1983-09-14 AU AU19117/83A patent/AU555544B2/en not_active Expired
- 1983-09-20 IL IL6977483A patent/IL69774A/xx not_active IP Right Cessation
- 1983-10-06 CA CA000438482A patent/CA1212686A/en not_active Expired
- 1983-10-07 DK DK462583A patent/DK174188B1/da not_active IP Right Cessation
- 1983-10-07 HU HU347683A patent/HU193185B/hu unknown
- 1983-10-11 ES ES526409A patent/ES526409A0/es active Granted
-
1990
- 1990-08-06 JP JP2206926A patent/JPH0660146B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE3369128D1 (en) | 1987-02-19 |
| HU193185B (en) | 1987-08-28 |
| GB8323361D0 (en) | 1983-10-05 |
| GR78644B (https=) | 1984-09-27 |
| AU1911783A (en) | 1984-04-19 |
| CA1212686A (en) | 1986-10-14 |
| AU555544B2 (en) | 1986-10-02 |
| JPH0660146B2 (ja) | 1994-08-10 |
| EP0106469A1 (en) | 1984-04-25 |
| NZ205561A (en) | 1987-08-31 |
| GB2130199A (en) | 1984-05-31 |
| DK462583A (da) | 1984-04-12 |
| JPH0372452A (ja) | 1991-03-27 |
| DK462583D0 (da) | 1983-10-07 |
| IL69774A (en) | 1987-01-30 |
| EP0106469B1 (en) | 1987-01-14 |
| ES8504683A1 (es) | 1985-04-16 |
| ES526409A0 (es) | 1985-04-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUP | Patent expired |