JP2002515483A5 - - Google Patents
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- JP2002515483A5 JP2002515483A5 JP2000549587A JP2000549587A JP2002515483A5 JP 2002515483 A5 JP2002515483 A5 JP 2002515483A5 JP 2000549587 A JP2000549587 A JP 2000549587A JP 2000549587 A JP2000549587 A JP 2000549587A JP 2002515483 A5 JP2002515483 A5 JP 2002515483A5
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- JP
- Japan
- Prior art keywords
- formula
- alkyl
- embedded image
- halogenoalkyl
- compound
- 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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- 125000000217 alkyl group Chemical group 0.000 description 39
- 150000001875 compounds Chemical class 0.000 description 27
- 125000001188 haloalkyl group Chemical group 0.000 description 26
- 229910052736 halogen Inorganic materials 0.000 description 22
- 150000002367 halogens Chemical group 0.000 description 22
- 125000003545 alkoxy group Chemical group 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 12
- 125000003342 alkenyl group Chemical group 0.000 description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- -1 carbonyloxy, oxycarbonyl Chemical group 0.000 description 10
- 125000000753 cycloalkyl group Chemical group 0.000 description 10
- 125000004438 haloalkoxy group Chemical group 0.000 description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 239000011593 sulfur Substances 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 125000004093 cyano group Chemical group *C#N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 description 2
- 125000005529 alkyleneoxy group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000004419 alkynylene group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000005702 oxyalkylene group Chemical group 0.000 description 2
- 125000003884 phenylalkyl group Chemical group 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- PEZNEXFPRSOYPL-UHFFFAOYSA-N (bis(trifluoroacetoxy)iodo)benzene Chemical compound FC(F)(F)C(=O)OI(OC(=O)C(F)(F)F)C1=CC=CC=C1 PEZNEXFPRSOYPL-UHFFFAOYSA-N 0.000 description 1
- ZDOYHCIRUPHUHN-UHFFFAOYSA-N 1-(2-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1Cl ZDOYHCIRUPHUHN-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JYRKVBLHMHSCDU-UHFFFAOYSA-N O=C(C1C(Cl)=CC=CC1)Cl Chemical compound O=C(C1C(Cl)=CC=CC1)Cl JYRKVBLHMHSCDU-UHFFFAOYSA-N 0.000 description 1
- BVHVFAVBNISXJS-UHFFFAOYSA-N [6-iodo-1-(2,2,2-trifluoroacetyl)oxycyclohexa-2,4-dien-1-yl] 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)OC1(OC(=O)C(F)(F)F)C=CC=CC1I BVHVFAVBNISXJS-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005620 boronic acid group Chemical class 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000021615 conjugation Effects 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
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 description 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- QDYBCIWLGJMJGO-UHFFFAOYSA-N dinitromethanone Chemical class [O-][N+](=O)C(=O)[N+]([O-])=O QDYBCIWLGJMJGO-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- JAVRNIFMYIJXIE-UHFFFAOYSA-N methyl 2-chlorobenzoate Chemical compound COC(=O)C1=CC=CC=C1Cl JAVRNIFMYIJXIE-UHFFFAOYSA-N 0.000 description 1
- 125000001326 naphthylalkyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- FEQAUBVIUZJXKN-UHFFFAOYSA-N propan-2-imine;hydrochloride Chemical compound [Cl-].CC(C)=[NH2+] FEQAUBVIUZJXKN-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19822247A DE19822247A1 (de) | 1998-05-18 | 1998-05-18 | 2-(2-Chlorphenyl)-3,4-dihydro-2H-pyrrol-Derivate |
| DE19822247.5 | 1998-05-18 | ||
| PCT/EP1999/003063 WO1999059968A1 (de) | 1998-05-18 | 1999-05-05 | 2-(2-chlorphenyl)-3,4-dihydro-2h-pyrrol-derivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002515483A JP2002515483A (ja) | 2002-05-28 |
| JP2002515483A5 true JP2002515483A5 (https=) | 2006-04-13 |
Family
ID=7868158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000549587A Pending JP2002515483A (ja) | 1998-05-18 | 1999-05-05 | ２−（２−クロロフェニル）−３，４−ジヒドロ−２ｈ−ピロール誘導体 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6489490B1 (https=) |
| EP (1) | EP1080072B1 (https=) |
| JP (1) | JP2002515483A (https=) |
| KR (1) | KR100629066B1 (https=) |
| CN (1) | CN1198800C (https=) |
| AR (1) | AR016489A1 (https=) |
| AT (1) | ATE272622T1 (https=) |
| AU (1) | AU747396B2 (https=) |
| BR (1) | BR9910539A (https=) |
| CA (1) | CA2332723A1 (https=) |
| CO (1) | CO5221031A1 (https=) |
| DE (2) | DE19822247A1 (https=) |
| ES (1) | ES2224666T3 (https=) |
| HU (1) | HUP0102615A3 (https=) |
| IL (1) | IL139117A0 (https=) |
| TR (1) | TR200003389T2 (https=) |
| WO (1) | WO1999059968A1 (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10047110A1 (de) * | 2000-09-22 | 2002-04-18 | Bayer Ag | Optisch aktive 2,5-Bisaryl-DELTA·1·-Pyrroline |
| DE10047109A1 (de) * | 2000-09-22 | 2002-04-11 | Bayer Ag | Verfahren zur Herstellung von DELTA·1·-Pyrrolinen |
| DE10047111A1 (de) * | 2000-09-22 | 2002-04-11 | Bayer Ag | Verfahren zur Herstellung von DELTA·1·-Pyrrolinen |
| IL154920A0 (en) * | 2000-09-22 | 2003-10-31 | Bayer Cropscience Ag | Delta 1-pyrrollines for use as pesticides |
| DE10047116A1 (de) * | 2000-09-22 | 2002-04-18 | Bayer Ag | DELTA·1·-Pyrroline |
| DE10060412A1 (de) | 2000-12-05 | 2002-06-06 | Bayer Ag | DELTA1-Pyrroline |
| DE10106457A1 (de) * | 2001-02-13 | 2002-08-14 | Bayer Ag | DELTA·1·-Pyrroline |
| DE10106455A1 (de) * | 2001-02-13 | 2002-08-14 | Bayer Ag | DELTA·1·-Pyrroline |
| CN1240678C (zh) | 2001-04-09 | 2006-02-08 | 拜尔农作物科学股份公司 | 制备△1－吡咯啉类化合物的方法 |
| DE10145772A1 (de) * | 2001-09-17 | 2003-04-10 | Bayer Cropscience Ag | DELTA·1·-Pyrroline |
| DE10154517A1 (de) * | 2001-11-07 | 2003-05-15 | Bayer Cropscience Ag | DELTA·1·-Pyrroline |
| DE10154515A1 (de) * | 2001-11-07 | 2003-05-15 | Bayer Cropscience Ag | DELTA·1·-Pyrroline |
| DE10204116A1 (de) * | 2002-02-01 | 2003-08-07 | Bayer Cropscience Ag | DELTA·1·-Pyrroline |
| DE10204115A1 (de) * | 2002-02-01 | 2003-08-07 | Bayer Cropscience Ag | DELTA·1·-Pyrroline |
| DE10243939A1 (de) * | 2002-09-24 | 2004-04-01 | Bayer Cropscience Ag | Pyrroline |
| EP1661886B1 (en) | 2003-08-29 | 2016-08-10 | Mitsui Chemicals Agro, Inc. | Insecticide for agricultural or horticultural use and method of use thereof |
| EP2080758A3 (de) | 2007-11-29 | 2009-08-26 | Bayer CropScience AG | Halogen substituierte delta-1-Pyrroline |
| CN102952056A (zh) * | 2011-08-19 | 2013-03-06 | 中国中化股份有限公司 | 一种含有七氟异丙基苯基的二苯基吡咯啉类化合物及其用途 |
| BR112014004945A2 (pt) * | 2011-09-01 | 2017-03-21 | Biotelliga Holdings Ltd | agentes lipídicos de inseticida isolados de fugos entomopatogênicos e usos dos mesmos |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1470386A1 (de) * | 1963-12-20 | 1969-05-29 | Union Carbide Corp | Verfahren zur Herstellung von substituierten Dihydropyrrolderivaten |
| FR2563696B1 (fr) * | 1984-05-04 | 1989-11-10 | Centre Nat Rech Scient | Compositions insecticides, notamment termicides, a base de derives 2,5-disubstitues de la pyrrolidine et/ou de la pyrroline-1 |
| FR2607361B1 (fr) * | 1986-12-01 | 1989-02-24 | Centre Nat Rech Scient | Compositions insecticides et/ou acaricides a base d'imines cycliques monosubstituees et procede de destruction des insectes et acariens |
| EP0712393A1 (de) * | 1993-08-05 | 1996-05-22 | Bayer Ag | Substituierte 4-carbamoyl-pyrrolin-2-on- und -dihydrofuran-2-on-derivate und deren verwendung als schädlingsbekämpfungsmittel |
| JPH0873446A (ja) * | 1994-04-22 | 1996-03-19 | Nippon Soda Co Ltd | ヘテロ環化合物および殺虫・殺ダニ剤 |
| 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 |
-
1998
- 1998-05-18 DE DE19822247A patent/DE19822247A1/de not_active Withdrawn
-
1999
- 1999-05-05 US US09/700,289 patent/US6489490B1/en not_active Expired - Fee Related
- 1999-05-05 AU AU41384/99A patent/AU747396B2/en not_active Ceased
- 1999-05-05 ES ES99924878T patent/ES2224666T3/es not_active Expired - Lifetime
- 1999-05-05 TR TR2000/03389T patent/TR200003389T2/xx unknown
- 1999-05-05 CN CNB998088072A patent/CN1198800C/zh not_active Expired - Fee Related
- 1999-05-05 HU HU0102615A patent/HUP0102615A3/hu unknown
- 1999-05-05 CA CA002332723A patent/CA2332723A1/en not_active Abandoned
- 1999-05-05 JP JP2000549587A patent/JP2002515483A/ja active Pending
- 1999-05-05 BR BR9910539-0A patent/BR9910539A/pt active Search and Examination
- 1999-05-05 AT AT99924878T patent/ATE272622T1/de not_active IP Right Cessation
- 1999-05-05 KR KR1020007012494A patent/KR100629066B1/ko not_active Expired - Fee Related
- 1999-05-05 IL IL13911799A patent/IL139117A0/xx unknown
- 1999-05-05 DE DE59910145T patent/DE59910145D1/de not_active Expired - Fee Related
- 1999-05-05 EP EP99924878A patent/EP1080072B1/de not_active Expired - Lifetime
- 1999-05-05 WO PCT/EP1999/003063 patent/WO1999059968A1/de not_active Ceased
- 1999-05-18 CO CO99030488A patent/CO5221031A1/es not_active Application Discontinuation
- 1999-05-18 AR ARP990102362A patent/AR016489A1/es active IP Right Grant
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