JP2005526055A5 - - Google Patents
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- Publication number
- JP2005526055A5 JP2005526055A5 JP2003572961A JP2003572961A JP2005526055A5 JP 2005526055 A5 JP2005526055 A5 JP 2005526055A5 JP 2003572961 A JP2003572961 A JP 2003572961A JP 2003572961 A JP2003572961 A JP 2003572961A JP 2005526055 A5 JP2005526055 A5 JP 2005526055A5
- Authority
- JP
- Japan
- Prior art keywords
- mmol
- added
- trifluoromethylphenyl
- dichloro
- cyano
- 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HILAMJUVRPHSKX-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(2-hydroxypropylamino)-4-(trifluoromethylsulfonyl)pyrazole-3-carbonitrile Chemical compound CC(O)CNC1=C(S(=O)(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl HILAMJUVRPHSKX-UHFFFAOYSA-N 0.000 description 1
- FYCUHRFODWYNGW-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(2-methoxyethylamino)-4-(trifluoromethylsulfonyl)pyrazole-3-carbonitrile Chemical compound COCCNC1=C(S(=O)(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl FYCUHRFODWYNGW-UHFFFAOYSA-N 0.000 description 1
- RWNLEWKZGWQRHK-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(propoxymethylamino)-4-(trifluoromethylsulfanyl)pyrazole-3-carbonitrile Chemical compound CCCOCNC1=C(SC(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl RWNLEWKZGWQRHK-UHFFFAOYSA-N 0.000 description 1
- VUWLOTIWBWVDCV-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[2-methoxyethyl(methyl)amino]-4-(trifluoromethylsulfonyl)pyrazole-3-carbonitrile Chemical compound COCCN(C)C1=C(S(=O)(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl VUWLOTIWBWVDCV-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- CBFIKOBUXGUSNV-UHFFFAOYSA-N 5-bromo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfonyl)pyrazole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(Br)=C(S(=O)(=O)C(F)(F)F)C(C#N)=N1 CBFIKOBUXGUSNV-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- FQXWEKADCSXYOC-UHFFFAOYSA-N fipronil-sulfide Chemical compound NC1=C(SC(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl FQXWEKADCSXYOC-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36132802P | 2002-03-05 | 2002-03-05 | |
| US60/361,328 | 2002-03-05 | ||
| EP02027033.6 | 2002-12-03 | ||
| EP02027033 | 2002-12-03 | ||
| PCT/EP2003/002009 WO2003074492A2 (en) | 2002-03-05 | 2003-02-27 | 5-substituted-alkylaminopyrazole derivatives as pesticides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005526055A JP2005526055A (ja) | 2005-09-02 |
| JP2005526055A5 true JP2005526055A5 (enExample) | 2010-09-02 |
| JP4696311B2 JP4696311B2 (ja) | 2011-06-08 |
Family
ID=44237171
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003572962A Pending JP2005530701A (ja) | 2002-03-05 | 2003-02-27 | 農薬としての５−置換アルキルアミノピラゾール誘導体 |
| JP2003572961A Expired - Lifetime JP4696311B2 (ja) | 2002-03-05 | 2003-02-27 | 農薬としての５−置換アルキルアミノピラゾール誘導体 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003572962A Pending JP2005530701A (ja) | 2002-03-05 | 2003-02-27 | 農薬としての５−置換アルキルアミノピラゾール誘導体 |
Country Status (16)
| Country | Link |
|---|---|
| EP (2) | EP1483246B1 (enExample) |
| JP (2) | JP2005530701A (enExample) |
| KR (2) | KR100969088B1 (enExample) |
| CN (2) | CN100532364C (enExample) |
| AT (2) | ATE335728T1 (enExample) |
| AU (2) | AU2003211629B8 (enExample) |
| BR (2) | BR0308135A (enExample) |
| DE (2) | DE60302558T2 (enExample) |
| DK (2) | DK1483245T3 (enExample) |
| ES (2) | ES2274210T3 (enExample) |
| NZ (1) | NZ535054A (enExample) |
| PL (2) | PL373026A1 (enExample) |
| PT (1) | PT1483245E (enExample) |
| RU (2) | RU2336272C2 (enExample) |
| SI (2) | SI1483245T1 (enExample) |
| WO (2) | WO2003074492A2 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7514464B2 (en) * | 2003-12-18 | 2009-04-07 | Pfizer Limited | Substituted arylpyrazoles |
| PL1727805T3 (pl) * | 2004-03-15 | 2009-01-30 | Merial Ltd | Pochodne 1-fenylo i 1-pirydylopirazolu oraz ich zastosowanie jako pestycydów |
| ES2345559T3 (es) | 2004-03-24 | 2010-09-27 | Merial Ltd. | Derivados de 5-aminoalquilpirazol como agentes pesticidas. |
| JP4890451B2 (ja) | 2004-06-26 | 2012-03-07 | メリアル リミテッド | １−アリール−アミノピロールに基づく殺虫剤 |
| JP4875614B2 (ja) | 2004-06-26 | 2012-02-15 | メリアル リミテッド | 殺虫剤としてのｎ−フェニルピラゾール誘導体 |
| MX2007000159A (es) * | 2004-06-26 | 2007-10-10 | Bayer Cropscience Sa | Derivados de n-fenilpirazol pesticidas. |
| CA2587429C (en) | 2004-12-07 | 2013-03-05 | Merial Limited | 5-aminopyrazole derivatives as pesticidal compounds |
| ES2377481T3 (es) * | 2005-01-21 | 2012-03-28 | Merial Ltd. | Derivados de pirazole como pesticidas. |
| UA94278C2 (ru) * | 2006-08-08 | 2011-04-26 | БАЙЕР КРОПСАЙЕНС ЭлПи | Способ обработки растений |
| CN100424139C (zh) * | 2006-08-25 | 2008-10-08 | 蒋文兰 | 凹凸棒悬浮剂 |
| DE102007003036A1 (de) | 2006-12-20 | 2008-06-26 | Bayer Cropscience Ag | Pyrimidinylpyrazole |
| RU2384065C2 (ru) * | 2007-12-10 | 2010-03-20 | Общество с ограниченной ответственностью "ЯДЖУР-ВЕДА" | Инсектоакарицидное средство |
| CN101998963B (zh) * | 2008-02-12 | 2014-09-24 | 陶氏益农公司 | 杀虫组合物 |
| US20110190365A1 (en) | 2008-08-14 | 2011-08-04 | Bayer Crop Science Ag | Insecticidal 4-phenyl-1H-pyrazoles |
| KR20110116220A (ko) * | 2009-02-11 | 2011-10-25 | 다우 아그로사이언시즈 엘엘씨 | 살충 조성물 |
| EP2398771B1 (en) | 2009-02-18 | 2015-07-29 | Boehringer Ingelheim International GmbH | Heterocyclic compounds which modulate the cb2 receptor |
| UA104057C2 (ru) * | 2009-10-21 | 2013-12-25 | Ніппон Сода Ко., Лтд. | Композиция приманки для борьбы с клещами |
| EP2523936A1 (en) | 2010-01-15 | 2012-11-21 | Boehringer Ingelheim International GmbH | Compounds which modulate the cb2 receptor |
| CN102206184B (zh) * | 2010-03-29 | 2013-07-10 | 南开大学 | 3-氰基-1-(2，6-二氯-4-三氟甲基苯基)吡唑衍生物杀虫剂 |
| WO2012012307A1 (en) * | 2010-07-22 | 2012-01-26 | Boehringer Ingelheim International Gmbh | Sulfonyl compounds which modulate the cb2 rece |
| TW201321367A (zh) * | 2011-10-25 | 2013-06-01 | Du Pont | 經１，３－二芳基取代之雜環殺蟲劑 |
| RU2483539C1 (ru) * | 2011-12-21 | 2013-06-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Башкирский государственный университет" | Средство для борьбы с грибковыми заболеваниями сельскохозяйственных культур |
| EP2803668A1 (en) | 2013-05-17 | 2014-11-19 | Boehringer Ingelheim International Gmbh | Novel (cyano-dimethyl-methyl)-isoxazoles and -[1,3,4]thiadiazoles |
| CN106187896B (zh) * | 2016-07-19 | 2018-07-31 | 中南民族大学 | 超声波喷雾微波辐射一体化制备芳基吡唑单或多烷基化衍生物 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8531485D0 (en) * | 1985-12-20 | 1986-02-05 | May & Baker Ltd | Compositions of matter |
| GB8713768D0 (en) * | 1987-06-12 | 1987-07-15 | May & Baker Ltd | Compositions of matter |
| DE4343832A1 (de) * | 1993-12-22 | 1995-06-29 | Bayer Ag | Substituierte 1-Arylpyrazole |
| GB9601128D0 (en) * | 1995-08-11 | 1996-03-20 | Pfizer Ltd | Parasiticidal compounds |
| JPH0987111A (ja) * | 1995-09-27 | 1997-03-31 | Sumitomo Chem Co Ltd | 害虫駆除用毒餌剤 |
| FR2739255B1 (fr) * | 1995-09-29 | 1998-09-04 | Rhone Merieux | Composition antiparasitaire pour le traitement et la protection des animaux de compagnie |
| GR1002899B (el) * | 1996-03-29 | 1998-05-11 | Rhone Merieux | Περιλαιμιο κατα ψυλλων και κροτωνων για σκυλους και γατες, με βαση ν-φαινυλπυραζολη |
| US6069157A (en) * | 1997-11-25 | 2000-05-30 | Pfizer Inc. | Parasiticidal compounds |
| DE19650197A1 (de) * | 1996-12-04 | 1998-06-10 | Bayer Ag | 3-Thiocarbamoylpyrazol-Derivate |
| CZ294766B6 (cs) * | 1996-12-24 | 2005-03-16 | Rhone-Poulenc Agro | 1-Arylpyrazolové sloučeniny, pesticidní prostředky obsahující tyto sloučeniny jako účinné látky a způsob hubení škůdců |
| US6350771B1 (en) * | 1996-12-24 | 2002-02-26 | Rhone-Poulenc, Inc. | Pesticidal 1-arylpyrazoles |
| AR021608A1 (es) * | 1998-12-11 | 2002-07-31 | Merial Ltd | Represion de artropodos en animales |
| CN101062920A (zh) * | 2000-06-09 | 2007-10-31 | 阿方蒂农科股份有限公司 | 除虫化合物的制备方法及其新的中间体 |
-
2003
- 2003-02-27 JP JP2003572962A patent/JP2005530701A/ja active Pending
- 2003-02-27 WO PCT/EP2003/002009 patent/WO2003074492A2/en not_active Ceased
- 2003-02-27 RU RU2004129578/04A patent/RU2336272C2/ru not_active IP Right Cessation
- 2003-02-27 EP EP03709725A patent/EP1483246B1/en not_active Expired - Lifetime
- 2003-02-27 SI SI200330522T patent/SI1483245T1/sl unknown
- 2003-02-27 DK DK03706583T patent/DK1483245T3/da active
- 2003-02-27 PL PL03373026A patent/PL373026A1/xx not_active Application Discontinuation
- 2003-02-27 WO PCT/EP2003/002010 patent/WO2003074493A1/en not_active Ceased
- 2003-02-27 NZ NZ535054A patent/NZ535054A/en not_active IP Right Cessation
- 2003-02-27 BR BR0308135-4A patent/BR0308135A/pt not_active Application Discontinuation
- 2003-02-27 DE DE60302558T patent/DE60302558T2/de not_active Expired - Fee Related
- 2003-02-27 ES ES03706583T patent/ES2274210T3/es not_active Expired - Lifetime
- 2003-02-27 DE DE60307438T patent/DE60307438T2/de not_active Expired - Lifetime
- 2003-02-27 CN CNB038069679A patent/CN100532364C/zh not_active Expired - Fee Related
- 2003-02-27 AU AU2003211629A patent/AU2003211629B8/en not_active Expired
- 2003-02-27 PT PT03706583T patent/PT1483245E/pt unknown
- 2003-02-27 EP EP03706583A patent/EP1483245B1/en not_active Expired - Lifetime
- 2003-02-27 AU AU2003221298A patent/AU2003221298B2/en not_active Expired
- 2003-02-27 AT AT03706583T patent/ATE335728T1/de active
- 2003-02-27 KR KR1020047013930A patent/KR100969088B1/ko not_active Expired - Fee Related
- 2003-02-27 BR BRPI0308189A patent/BRPI0308189B1/pt not_active IP Right Cessation
- 2003-02-27 RU RU2004129579/04A patent/RU2308452C2/ru not_active IP Right Cessation
- 2003-02-27 AT AT03709725T patent/ATE311367T1/de active
- 2003-02-27 DK DK03709725T patent/DK1483246T3/da active
- 2003-02-27 JP JP2003572961A patent/JP4696311B2/ja not_active Expired - Lifetime
- 2003-02-27 CN CN03806961XA patent/CN1642920B/zh not_active Expired - Fee Related
- 2003-02-27 SI SI200330132T patent/SI1483246T1/sl unknown
- 2003-02-27 ES ES03709725T patent/ES2249709T3/es not_active Expired - Lifetime
- 2003-02-27 KR KR1020047013964A patent/KR100966012B1/ko not_active Expired - Fee Related
- 2003-02-27 PL PL03372918A patent/PL372918A1/xx not_active Application Discontinuation
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