JP2005518349A5 - - Google Patents
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- Publication number
- JP2005518349A5 JP2005518349A5 JP2003542176A JP2003542176A JP2005518349A5 JP 2005518349 A5 JP2005518349 A5 JP 2005518349A5 JP 2003542176 A JP2003542176 A JP 2003542176A JP 2003542176 A JP2003542176 A JP 2003542176A JP 2005518349 A5 JP2005518349 A5 JP 2005518349A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- pyrroline
- compound
- alkyl
- chlorine
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 15
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N 1-Pyrroline Chemical compound C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 10
- -1 cyclopropylethyl Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 5
- PWATUXGJXJPDET-UHFFFAOYSA-N 5,5-dimethyl-1,3,2-dioxaborinane Chemical compound CC1(C)COBOC1 PWATUXGJXJPDET-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- UCFSYHMCKWNKAH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 claims description 2
- ARSUQHZDPBOKDP-UHFFFAOYSA-N 4,4,6-trimethyl-1,3,2-dioxaborinane Chemical compound CC1CC(C)(C)OBO1 ARSUQHZDPBOKDP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 7
- 229910052731 fluorine Inorganic materials 0.000 claims 7
- 239000011737 fluorine Substances 0.000 claims 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 239000001301 oxygen Substances 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 239000011593 sulfur Substances 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 241000607479 Yersinia pestis Species 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000004067 bulking agent Substances 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 239000002917 insecticide Substances 0.000 claims 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
- 239000004094 surface-active agent Substances 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000010523 cascade reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 150000002902 organometallic compounds Chemical class 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- MDNDJMCSXOXBFZ-UHFFFAOYSA-N 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane Chemical compound O1CC(C)(C)COB1B1OCC(C)(C)CO1 MDNDJMCSXOXBFZ-UHFFFAOYSA-N 0.000 description 2
- UEBSWKNVDRJVHN-UHFFFAOYSA-N 4,4,6-trimethyl-2-(4,4,6-trimethyl-1,3,2-dioxaborinan-2-yl)-1,3,2-dioxaborinane Chemical compound O1C(C)CC(C)(C)OB1B1OC(C)(C)CC(C)O1 UEBSWKNVDRJVHN-UHFFFAOYSA-N 0.000 description 2
- 0 CC(**)(C=C1)NC=C1c1ccc(C(CC2)N=C2c2c(*)cccc2*)cc1 Chemical compound CC(**)(C=C1)NC=C1c1ccc(C(CC2)N=C2c2c(*)cccc2*)cc1 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- UONCERAQKBPLML-UHFFFAOYSA-N (6-ethoxypyridin-3-yl)boronic acid Chemical compound CCOC1=CC=C(B(O)O)C=N1 UONCERAQKBPLML-UHFFFAOYSA-N 0.000 description 1
- WYBQOWXCLDXZNR-UHFFFAOYSA-N 2-(1,3,2-benzodioxaborol-2-yl)-1,3,2-benzodioxaborole Chemical compound O1C2=CC=CC=C2OB1B1OC2=CC=CC=C2O1 WYBQOWXCLDXZNR-UHFFFAOYSA-N 0.000 description 1
- FOGDFVUQHQEIPV-UHFFFAOYSA-N 2-(1,3,2-dioxaborinan-2-yl)-1,3,2-dioxaborinane Chemical compound O1CCCOB1B1OCCCO1 FOGDFVUQHQEIPV-UHFFFAOYSA-N 0.000 description 1
- LZPWAYBEOJRFAX-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2$l^{2}-dioxaborolane Chemical compound CC1(C)O[B]OC1(C)C LZPWAYBEOJRFAX-UHFFFAOYSA-N 0.000 description 1
- FRYRJNHMRVINIZ-UHFFFAOYSA-N B1CCOO1 Chemical compound B1CCOO1 FRYRJNHMRVINIZ-UHFFFAOYSA-N 0.000 description 1
- MTEUMUKGQMPAOT-UHFFFAOYSA-N [4-[5-(2,6-difluorophenyl)-3,4-dihydro-2h-pyrrol-2-yl]phenyl] trifluoromethanesulfonate Chemical compound FC1=CC=CC(F)=C1C1=NC(C=2C=CC(OS(=O)(=O)C(F)(F)F)=CC=2)CC1 MTEUMUKGQMPAOT-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10154515A DE10154515A1 (de) | 2001-11-07 | 2001-11-07 | DELTA·1·-Pyrroline |
| PCT/EP2002/012259 WO2003040130A1 (de) | 2001-11-07 | 2002-11-04 | Δ1-pyrroline |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005518349A JP2005518349A (ja) | 2005-06-23 |
| JP2005518349A5 true JP2005518349A5 (https=) | 2009-09-24 |
| JP4381141B2 JP4381141B2 (ja) | 2009-12-09 |
Family
ID=7704818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003542176A Expired - Lifetime JP4381141B2 (ja) | 2001-11-07 | 2002-11-04 | Δ１−ピロリン |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US7115603B2 (https=) |
| EP (1) | EP1448549B1 (https=) |
| JP (1) | JP4381141B2 (https=) |
| KR (1) | KR100930072B1 (https=) |
| CN (1) | CN100376566C (https=) |
| AR (1) | AR037155A1 (https=) |
| AT (1) | ATE345337T1 (https=) |
| AU (1) | AU2002340498B2 (https=) |
| BR (1) | BR0213912A (https=) |
| CA (1) | CA2466066A1 (https=) |
| CO (1) | CO5590959A2 (https=) |
| DE (2) | DE10154515A1 (https=) |
| ES (1) | ES2274102T3 (https=) |
| MX (1) | MXPA04004262A (https=) |
| NZ (1) | NZ532725A (https=) |
| PT (1) | PT1448549E (https=) |
| TW (1) | TWI251592B (https=) |
| WO (1) | WO2003040130A1 (https=) |
| ZA (1) | ZA200403387B (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2008013305A (es) * | 2006-04-20 | 2008-10-27 | Du Pont | Agentes heterociclicos de cinco miembros para el control de plagas de invertebrados. |
| EP2080758A3 (de) * | 2007-11-29 | 2009-08-26 | Bayer CropScience AG | Halogen substituierte delta-1-Pyrroline |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0702670A1 (de) | 1993-06-07 | 1996-03-27 | Bayer Ag | Iodpropargylcarbamate und ihre verwendung als biozide im pflanzen- und materialschutz |
| DE19648011A1 (de) * | 1996-11-20 | 1998-05-28 | Bayer Ag | Cyclische Imine |
| DE19822245A1 (de) | 1998-05-18 | 1999-11-25 | Bayer Ag | 2-(2-Methylphenyl)-3,4-dihydro-2H-pyrrol- Derivate |
| DE19822247A1 (de) | 1998-05-18 | 1999-11-25 | Bayer Ag | 2-(2-Chlorphenyl)-3,4-dihydro-2H-pyrrol-Derivate |
| DE19847076A1 (de) | 1998-10-14 | 2000-04-20 | Bayer Ag | 2-Hetaryl-3,4-dihydro-2H-pyrrol-Derivate |
| DE10060412A1 (de) * | 2000-12-05 | 2002-06-06 | Bayer Ag | DELTA1-Pyrroline |
-
2001
- 2001-11-07 DE DE10154515A patent/DE10154515A1/de not_active Withdrawn
-
2002
- 2002-10-30 AR ARP020104123A patent/AR037155A1/es unknown
- 2002-11-04 JP JP2003542176A patent/JP4381141B2/ja not_active Expired - Lifetime
- 2002-11-04 AT AT02774765T patent/ATE345337T1/de not_active IP Right Cessation
- 2002-11-04 BR BR0213912-0A patent/BR0213912A/pt not_active IP Right Cessation
- 2002-11-04 WO PCT/EP2002/012259 patent/WO2003040130A1/de not_active Ceased
- 2002-11-04 PT PT02774765T patent/PT1448549E/pt unknown
- 2002-11-04 CA CA002466066A patent/CA2466066A1/en not_active Abandoned
- 2002-11-04 MX MXPA04004262A patent/MXPA04004262A/es active IP Right Grant
- 2002-11-04 NZ NZ532725A patent/NZ532725A/en not_active IP Right Cessation
- 2002-11-04 CN CNB028268628A patent/CN100376566C/zh not_active Expired - Fee Related
- 2002-11-04 ES ES02774765T patent/ES2274102T3/es not_active Expired - Lifetime
- 2002-11-04 US US10/494,204 patent/US7115603B2/en not_active Expired - Fee Related
- 2002-11-04 DE DE50208731T patent/DE50208731D1/de not_active Expired - Lifetime
- 2002-11-04 EP EP02774765A patent/EP1448549B1/de not_active Expired - Lifetime
- 2002-11-04 KR KR1020047006288A patent/KR100930072B1/ko not_active Expired - Fee Related
- 2002-11-04 AU AU2002340498A patent/AU2002340498B2/en not_active Ceased
- 2002-11-06 TW TW091132633A patent/TWI251592B/zh not_active IP Right Cessation
-
2004
- 2004-05-05 ZA ZA200403387A patent/ZA200403387B/en unknown
- 2004-06-04 CO CO04052677A patent/CO5590959A2/es not_active Application Discontinuation
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