JP2004504383A5 - - Google Patents
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- Publication number
- JP2004504383A5 JP2004504383A5 JP2002514103A JP2002514103A JP2004504383A5 JP 2004504383 A5 JP2004504383 A5 JP 2004504383A5 JP 2002514103 A JP2002514103 A JP 2002514103A JP 2002514103 A JP2002514103 A JP 2002514103A JP 2004504383 A5 JP2004504383 A5 JP 2004504383A5
- Authority
- JP
- Japan
- Prior art keywords
- fluorine
- chlorine
- bromine
- alkyl
- hydrogen
- 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 90
- 229910052801 chlorine Inorganic materials 0.000 description 90
- 239000000460 chlorine Substances 0.000 description 90
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 89
- 229910052731 fluorine Inorganic materials 0.000 description 89
- 239000011737 fluorine Substances 0.000 description 89
- -1 cyano, hydroxy, carboxyl Chemical group 0.000 description 82
- 229910052739 hydrogen Inorganic materials 0.000 description 76
- 239000001257 hydrogen Substances 0.000 description 76
- 150000002431 hydrogen Chemical group 0.000 description 71
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 61
- 125000005843 halogen group Chemical group 0.000 description 60
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 52
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 52
- 229910052794 bromium Inorganic materials 0.000 description 52
- 125000001188 haloalkyl group Chemical group 0.000 description 47
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 42
- 125000000217 alkyl group Chemical group 0.000 description 39
- 125000001246 bromo group Chemical group Br* 0.000 description 38
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 28
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 27
- 229910052736 halogen Inorganic materials 0.000 description 25
- 150000002367 halogens Chemical class 0.000 description 25
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 24
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 15
- 125000004093 cyano group Chemical group *C#N 0.000 description 13
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical group CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 8
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- 0 Cc1c(*)[n](*)nc1C Chemical compound Cc1c(*)[n](*)nc1C 0.000 description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 125000004438 haloalkoxy group Chemical group 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 6
- GTKIGDZXPDCIKR-UHFFFAOYSA-N 2-phenylbenzamide Chemical class NC(=O)C1=CC=CC=C1C1=CC=CC=C1 GTKIGDZXPDCIKR-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 description 3
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 3
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005262 alkoxyamine group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000005133 alkynyloxy group Chemical group 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- JFXFHKGKVJMEAV-UHFFFAOYSA-N n-ethyl-2-phenylbenzamide Chemical class CCNC(=O)C1=CC=CC=C1C1=CC=CC=C1 JFXFHKGKVJMEAV-UHFFFAOYSA-N 0.000 description 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10035857.8 | 2000-07-24 | ||
| DE10035857 | 2000-07-24 | ||
| DE10122447A DE10122447A1 (de) | 2000-07-24 | 2001-05-09 | Biphenylcarboxamide |
| DE10122447.8 | 2001-05-09 | ||
| PCT/EP2001/007981 WO2002008197A1 (de) | 2000-07-24 | 2001-07-11 | Biphenylcarboxamide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004504383A JP2004504383A (ja) | 2004-02-12 |
| JP2004504383A5 true JP2004504383A5 (enExample) | 2008-08-28 |
| JP4825395B2 JP4825395B2 (ja) | 2011-11-30 |
Family
ID=7649938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002514103A Expired - Fee Related JP4825395B2 (ja) | 2000-07-24 | 2001-07-11 | ビフェニルカルボキシアミド類 |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP4825395B2 (enExample) |
| KR (1) | KR100772457B1 (enExample) |
| DE (1) | DE10122447A1 (enExample) |
| ZA (1) | ZA200300633B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007502312A (ja) * | 2003-05-21 | 2007-02-08 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | ジフロオロメチルベンズアニリド類 |
| WO2006027193A1 (de) * | 2004-09-06 | 2006-03-16 | Basf Aktiengesellschaft | (hetero)cyclyl(thio) carbonsäureanilide zur bekämpfung von schadpilzen |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3208089A1 (de) * | 1982-03-06 | 1983-09-08 | Merck Patent Gmbh, 6100 Darmstadt | Halogenbiphenylderivate |
| GB9817548D0 (en) * | 1998-08-12 | 1998-10-07 | Novartis Ag | Organic compounds |
| DE19840322A1 (de) * | 1998-09-04 | 2000-03-09 | Bayer Ag | Pyrazol-carboxanilide |
| JP2001335550A (ja) * | 2000-05-26 | 2001-12-04 | Sumitomo Chem Co Ltd | ジハロプロペン化合物、その用途およびその製造中間体 |
| US6992098B2 (en) * | 2000-07-24 | 2006-01-31 | Bayer Cropscience Ag | Pyrazolyl biphenyl carboxamides and the use thereof for controlling undesired microorganisms |
| US6919382B2 (en) * | 2000-08-31 | 2005-07-19 | The Governors Of The University Of Alberta | Preparation and uses of conjugated solid supports for boronic acids |
-
2001
- 2001-05-09 DE DE10122447A patent/DE10122447A1/de not_active Withdrawn
- 2001-07-11 JP JP2002514103A patent/JP4825395B2/ja not_active Expired - Fee Related
- 2001-07-11 KR KR1020037000346A patent/KR100772457B1/ko not_active Expired - Fee Related
-
2003
- 2003-01-23 ZA ZA200300633A patent/ZA200300633B/xx unknown
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