ZA200403387B - "Delta<1>-pyrrolines. - Google Patents
"Delta<1>-pyrrolines. Download PDFInfo
- Publication number
- ZA200403387B ZA200403387B ZA200403387A ZA200403387A ZA200403387B ZA 200403387 B ZA200403387 B ZA 200403387B ZA 200403387 A ZA200403387 A ZA 200403387A ZA 200403387 A ZA200403387 A ZA 200403387A ZA 200403387 B ZA200403387 B ZA 200403387B
- Authority
- ZA
- South Africa
- Prior art keywords
- formula
- pyrrolines
- alkyl
- appropriate
- chlorine
- Prior art date
Links
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- -1 cyclopropylethyl Chemical group 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 239000005864 Sulphur Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000011230 binding agent Substances 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 7
- 241000607479 Yersinia pestis Species 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 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 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000000575 pesticide Substances 0.000 claims description 4
- 238000010523 cascade reaction Methods 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
- 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 description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002902 organometallic compounds Chemical class 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000004606 Fillers/Extenders Substances 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- YKFRAOGHWKADFJ-UHFFFAOYSA-N Aramite Chemical compound ClCCOS(=O)OC(C)COC1=CC=C(C(C)(C)C)C=C1 YKFRAOGHWKADFJ-UHFFFAOYSA-N 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- 239000003899 bactericide agent Substances 0.000 claims 1
- 230000000855 fungicidal effect Effects 0.000 claims 1
- 239000000417 fungicide Substances 0.000 claims 1
- 239000002917 insecticide Substances 0.000 claims 1
- 239000005645 nematicide Substances 0.000 claims 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 229910052763 palladium Inorganic materials 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- YRUSDPXROXBLGQ-UHFFFAOYSA-N 2-(4-bromophenyl)-5-(2,6-difluorophenyl)-3,4-dihydro-2h-pyrrole Chemical compound FC1=CC=CC(F)=C1C1=NC(C=2C=CC(Br)=CC=2)CC1 YRUSDPXROXBLGQ-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance 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
- YFTHTJAPODJVSL-UHFFFAOYSA-N 2-(1-benzothiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(SC=C2)C2=C1 YFTHTJAPODJVSL-UHFFFAOYSA-N 0.000 description 1
- AKVRNQXXWSWRLT-UHFFFAOYSA-N 5-(2,6-difluorophenyl)-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3,4-dihydro-2h-pyrrole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C2N=C(CC2)C=2C(=CC=CC=2F)F)C=C1 AKVRNQXXWSWRLT-UHFFFAOYSA-N 0.000 description 1
- FSZRSTNRZUIEMA-UHFFFAOYSA-N 5-bromo-2-propan-2-yloxypyridine Chemical compound CC(C)OC1=CC=C(Br)C=N1 FSZRSTNRZUIEMA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- MEJCPATZNWTSBX-UHFFFAOYSA-N tributyl-(6-ethoxypyridin-3-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=C(OCC)N=C1 MEJCPATZNWTSBX-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10154515A DE10154515A1 (de) | 2001-11-07 | 2001-11-07 | DELTA·1·-Pyrroline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200403387B true ZA200403387B (en) | 2005-05-05 |
Family
ID=7704818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200403387A ZA200403387B (en) | 2001-11-07 | 2004-05-05 | "Delta<1>-pyrrolines. |
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
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003040130A1 (de) | 2003-05-15 |
| NZ532725A (en) | 2005-11-25 |
| AU2002340498B2 (en) | 2007-11-29 |
| CA2466066A1 (en) | 2003-05-15 |
| DE10154515A1 (de) | 2003-05-15 |
| CN1701070A (zh) | 2005-11-23 |
| US20050228028A1 (en) | 2005-10-13 |
| KR20050043727A (ko) | 2005-05-11 |
| JP4381141B2 (ja) | 2009-12-09 |
| KR100930072B1 (ko) | 2009-12-08 |
| TW200303314A (en) | 2003-09-01 |
| PT1448549E (pt) | 2007-01-31 |
| MXPA04004262A (es) | 2004-07-08 |
| DE50208731D1 (de) | 2006-12-28 |
| CO5590959A2 (es) | 2005-12-30 |
| JP2005518349A (ja) | 2005-06-23 |
| EP1448549B1 (de) | 2006-11-15 |
| BR0213912A (pt) | 2004-09-28 |
| ATE345337T1 (de) | 2006-12-15 |
| TWI251592B (en) | 2006-03-21 |
| EP1448549A1 (de) | 2004-08-25 |
| AR037155A1 (es) | 2004-10-27 |
| US7115603B2 (en) | 2006-10-03 |
| ES2274102T3 (es) | 2007-05-16 |
| CN100376566C (zh) | 2008-03-26 |
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