JP2003512456A5 - - Google Patents
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- Publication number
- JP2003512456A5 JP2003512456A5 JP2001533114A JP2001533114A JP2003512456A5 JP 2003512456 A5 JP2003512456 A5 JP 2003512456A5 JP 2001533114 A JP2001533114 A JP 2001533114A JP 2001533114 A JP2001533114 A JP 2001533114A JP 2003512456 A5 JP2003512456 A5 JP 2003512456A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- process according
- compound
- disulfide
- iii
- 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
- 238000000034 method Methods 0.000 description 41
- 150000001875 compounds Chemical class 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 9
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 125000001188 haloalkyl group Chemical group 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- RJCQBQGAPKAMLL-UHFFFAOYSA-N bromotrifluoromethane Chemical compound FC(F)(F)Br RJCQBQGAPKAMLL-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000002228 disulfide group Chemical group 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000004438 haloalkoxy group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- FPPLREPCQJZDAQ-UHFFFAOYSA-N 2-methylpentanedinitrile Chemical compound N#CC(C)CCC#N FPPLREPCQJZDAQ-UHFFFAOYSA-N 0.000 description 1
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 description 1
- KYWRZLCFDFEWBI-UHFFFAOYSA-N 5-amino-4-[[5-amino-3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazol-4-yl]disulfanyl]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole-3-carbonitrile Chemical compound N#CC1=NN(C=2C(=CC(=CC=2Cl)C(F)(F)F)Cl)C(N)=C1SSC(C(=N1)C#N)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl KYWRZLCFDFEWBI-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 0 CC*1c(*(*=C2*)C(C)=C2O)c(*)cc(*)c1 Chemical compound CC*1c(*(*=C2*)C(C)=C2O)c(*)cc(*)c1 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- -1 aromatic nitrile Chemical class 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004821 distillation 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
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP1999/008687 WO2001030760A1 (en) | 1999-10-22 | 1999-10-22 | Process for preparing 4-trifluoromethylsulphinylpyrazole derivative |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003512456A JP2003512456A (ja) | 2003-04-02 |
| JP2003512456A5 true JP2003512456A5 (enExample) | 2006-12-14 |
| JP4666863B2 JP4666863B2 (ja) | 2011-04-06 |
Family
ID=8167491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001533114A Expired - Fee Related JP4666863B2 (ja) | 1999-10-22 | 1999-10-22 | ４−トリフルオロメチルスルフィニルピラゾール誘導体の調製プロセス |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US6620943B1 (enExample) |
| EP (1) | EP1222173B1 (enExample) |
| JP (1) | JP4666863B2 (enExample) |
| KR (2) | KR100665599B1 (enExample) |
| CN (3) | CN1163488C (enExample) |
| AT (1) | ATE273961T1 (enExample) |
| AU (1) | AU783139B2 (enExample) |
| BG (1) | BG65483B1 (enExample) |
| BR (1) | BR9917518B1 (enExample) |
| CA (1) | CA2384283C (enExample) |
| CZ (1) | CZ299822B6 (enExample) |
| DE (1) | DE69919599T2 (enExample) |
| DK (1) | DK1222173T3 (enExample) |
| EA (1) | EA005077B1 (enExample) |
| ES (1) | ES2222743T3 (enExample) |
| HR (1) | HRP20020438B1 (enExample) |
| HU (1) | HU229393B1 (enExample) |
| IL (2) | IL149152A0 (enExample) |
| IN (2) | IN2005MU00818A (enExample) |
| ME (1) | MEP7808A (enExample) |
| MX (1) | MX229662B (enExample) |
| NZ (2) | NZ527896A (enExample) |
| PL (1) | PL206482B1 (enExample) |
| PT (1) | PT1222173E (enExample) |
| RO (1) | RO121209B1 (enExample) |
| TR (2) | TR200202806T2 (enExample) |
| TW (1) | TW553936B (enExample) |
| UA (1) | UA73752C2 (enExample) |
| WO (1) | WO2001030760A1 (enExample) |
| ZA (1) | ZA200201961B (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1160349C (zh) | 1999-06-29 | 2004-08-04 | 日本农药株式会社 | 吡唑衍生物及其制备方法,以及含有该衍生物作为有效成分的有害生物防治剂 |
| WO2005023774A1 (en) * | 2003-09-11 | 2005-03-17 | Cheminova A/S | Process for the preparation of a trifluoromethylthioether |
| CN100586934C (zh) * | 2003-11-07 | 2010-02-03 | 凯米诺瓦有限公司 | 制备三氟甲基硫醚的方法 |
| DE102004020069C5 (de) | 2004-04-24 | 2013-12-05 | Voith Patent Gmbh | Verfahren zum Satinieren einer Papierbahn |
| AU2013203228B2 (en) * | 2005-12-14 | 2015-08-27 | Makhteshim Chemical Works Ltd | Polymorphs and amorphous forms of 5-amino-1-[2,6- dichloro-4-(trifluoromethyl)phenyl]-4- [(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile |
| KR20080077650A (ko) | 2005-12-14 | 2008-08-25 | 마켓심 케미칼 웍스 리미티드 | 5-아미노-1-[2,6-디클로로-4-(트리플루오로메틸)페닐]-4-[(트리플루오로메틸)설피닐]-1ｈ-피라졸-ｓ-카르보니트릴의다형체 및 무정형 |
| US7777052B2 (en) | 2006-04-25 | 2010-08-17 | Gharda Chemicals Limited | Process for the preparation of Fipronil, an insecticide, and related pyrazoles |
| CN101168529B (zh) * | 2006-10-24 | 2011-03-23 | 温州大学 | 氟虫腈、乙虫腈及其衍生物的合成方法 |
| WO2008055882A1 (en) | 2006-11-10 | 2008-05-15 | Basf Se | Crystalline modification of fipronil |
| KR20090083454A (ko) | 2006-11-10 | 2009-08-03 | 바스프 에스이 | 피라졸 유도체의 술피닐화 방법 |
| UA110598C2 (uk) * | 2006-11-10 | 2016-01-25 | Басф Се | Спосіб одержання кристалічної модифікації фіпронілу |
| BRPI0718774A2 (pt) | 2006-11-10 | 2013-12-03 | Basf Se | "processo para a sulfinilação de um derivado de pirazol, 5-amino-1-[2,6-dicloro-4-(trifluorometil) fenil] -4-(trifluorometilsulfinil) -pirazol-3-carbonitrila, composição pesticida ou parasiticida, uso, métodos para o controle de insetos, acarídeos ou nematódeos, de proteger plantas em crescimento, para tratar, controlar, prevenir ou proteger animais, e, processo para a preparação de uma composição." |
| CA2667112C (en) | 2006-11-10 | 2015-08-11 | Basf Se | Crystalline modification of fipronil |
| AU2007316641B2 (en) * | 2006-11-10 | 2013-01-10 | Basf Se | Crystalline modification of fipronil |
| JP5486603B2 (ja) | 2008-10-02 | 2014-05-07 | ビーエーエスエフ ソシエタス・ヨーロピア | トリフルオロメタンスルフィン酸の製造方法および精製方法 |
| WO2010049746A1 (en) * | 2008-10-27 | 2010-05-06 | Dynamit Nobel Gmbh Explosivstoff-Und Systemtechnic | Process for the synthesis of fipronil |
| CN102574810B (zh) * | 2009-10-30 | 2015-01-28 | 巴斯夫欧洲公司 | 制备4-亚磺酰基吡唑衍生物的方法 |
| AU2010100462A4 (en) | 2010-03-03 | 2010-06-17 | Keki Hormusji Gharda | A process for the synthesis of Fipronil |
| IT1400666B1 (it) | 2010-07-07 | 2013-06-28 | Finchimica Srl | Procedimento per la sintesi di 5-amino, 1-fenil, 3-ciano, 4-trifluorometil sulfinil pirazoli. |
| US20130197238A1 (en) | 2010-07-12 | 2013-08-01 | Irvita Plant Protection, A Branch Of Celsius Property B.V | Fipronil production process |
| EP2663192A4 (en) * | 2011-01-14 | 2015-06-03 | Keki Hormusji Gharda | POLYMORPHISMS IN 5-AMINO-1- (2,6-DICHLOR-4-TRIFLUOROMETHYLPHENYL-) 3-CYAN-4-TRIFLUOR-METHYL-SULFINYL-PYRAZOLE |
| US9029564B2 (en) | 2011-05-30 | 2015-05-12 | Keki Hormusji Gharda | Process for synthesis of fipronil |
| CN102633722B (zh) * | 2012-03-20 | 2015-05-06 | 金坛市凌云动物保健品有限公司 | 一种非泼罗尼的制备方法 |
| TWI579274B (zh) * | 2012-04-20 | 2017-04-21 | 龍馬躍公司 | 製備１－芳基－５－烷基吡唑化合物的改良方法 |
| CN102690232A (zh) * | 2012-05-30 | 2012-09-26 | 河南中医学院 | 一种氟虫腈中间体的合成方法 |
| US9049860B2 (en) | 2013-04-17 | 2015-06-09 | The Hartz Mountain Corporation | Ectoparasiticidal methods |
| CN105254565A (zh) * | 2015-09-30 | 2016-01-20 | 乐平市康鑫医药化工有限公司 | 由氰基吡唑一锅法合成硫醚的工艺方法 |
| CN106977460A (zh) * | 2017-04-19 | 2017-07-25 | 江苏托球农化股份有限公司 | 1‑(2,6‑二氯‑4‑三氟甲基)苯基‑3‑氰基‑4‑乙巯基‑5‑氨基吡唑的合成 |
| EP3412658A1 (en) | 2017-06-09 | 2018-12-12 | Solvay Sa | Processes for the manufacture of sulfur-substitued pyrazole derivatives |
| EP3412659A1 (en) | 2017-06-09 | 2018-12-12 | Solvay Sa | Processes for the manufacture of sulfur-substituted pyrazole derivatives |
| CN112430213A (zh) * | 2020-12-03 | 2021-03-02 | 江苏优普生物化学科技股份有限公司 | 一种三氟甲硫基吡唑合成工艺 |
| CN113149909B (zh) * | 2021-03-24 | 2022-04-19 | 台州达辰药业有限公司 | 5-氨基-3-氰基-1-(2,6-二氯-4-三氟甲基-苯基)吡唑二硫化物制备方法 |
| CN113480482B (zh) * | 2021-07-05 | 2022-11-18 | 海正药业南通有限公司 | 一种非泼罗尼中间体的合成方法 |
| CN114213330A (zh) * | 2021-12-29 | 2022-03-22 | 天和药业股份有限公司 | 一种氟虫腈精制母液的处理方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2716453B1 (fr) * | 1994-02-22 | 1996-03-29 | Rhone Poulenc Agrochimie | Procédé de sulfinylation de composés hétérocycliques. |
| DE3602728A1 (de) * | 1985-05-17 | 1986-11-20 | Bayer Ag, 51373 Leverkusen | Schaedlingsbekaempfungsmittel auf basis von pyrazolderivaten |
| US5232940A (en) | 1985-12-20 | 1993-08-03 | Hatton Leslie R | Derivatives of N-phenylpyrazoles |
| GB8713768D0 (en) | 1987-06-12 | 1987-07-15 | May & Baker Ltd | Compositions of matter |
| US5547974A (en) * | 1985-12-20 | 1996-08-20 | Rhone-Poulenc Agriculture Ltd. | Derivatives of N-phenylpyrazoles |
| CA2004776C (fr) * | 1988-12-13 | 2000-04-25 | Claude Wakselman | Procede de preparation de perfluoroalkylthioethers |
-
1999
- 1999-10-22 NZ NZ527896A patent/NZ527896A/en not_active IP Right Cessation
- 1999-10-22 RO ROA200200317A patent/RO121209B1/ro unknown
- 1999-10-22 PL PL354611A patent/PL206482B1/pl not_active IP Right Cessation
- 1999-10-22 JP JP2001533114A patent/JP4666863B2/ja not_active Expired - Fee Related
- 1999-10-22 PT PT99955978T patent/PT1222173E/pt unknown
- 1999-10-22 TR TR2002/02806T patent/TR200202806T2/xx unknown
- 1999-10-22 ES ES99955978T patent/ES2222743T3/es not_active Expired - Lifetime
- 1999-10-22 DE DE69919599T patent/DE69919599T2/de not_active Expired - Lifetime
- 1999-10-22 CN CNB998060828A patent/CN1163488C/zh not_active Expired - Lifetime
- 1999-10-22 EP EP99955978A patent/EP1222173B1/en not_active Expired - Lifetime
- 1999-10-22 TR TR2002/01072T patent/TR200201072T2/xx unknown
- 1999-10-22 CN CN2008101863366A patent/CN101445483B/zh not_active Expired - Lifetime
- 1999-10-22 EA EA200200481A patent/EA005077B1/ru not_active IP Right Cessation
- 1999-10-22 DK DK99955978T patent/DK1222173T3/da active
- 1999-10-22 IN IN818MU2005 patent/IN2005MU00818A/en unknown
- 1999-10-22 KR KR1020067017067A patent/KR100665599B1/ko not_active Expired - Fee Related
- 1999-10-22 NZ NZ517770A patent/NZ517770A/en not_active IP Right Cessation
- 1999-10-22 HR HR20020438A patent/HRP20020438B1/xx not_active IP Right Cessation
- 1999-10-22 MX MXPA02003944 patent/MX229662B/es active IP Right Grant
- 1999-10-22 AU AU12707/00A patent/AU783139B2/en not_active Expired
- 1999-10-22 BR BRPI9917518-5A patent/BR9917518B1/pt not_active IP Right Cessation
- 1999-10-22 US US10/111,000 patent/US6620943B1/en not_active Expired - Lifetime
- 1999-10-22 HU HU0203206A patent/HU229393B1/hu unknown
- 1999-10-22 IL IL14915299A patent/IL149152A0/xx active IP Right Grant
- 1999-10-22 WO PCT/EP1999/008687 patent/WO2001030760A1/en not_active Ceased
- 1999-10-22 ME MEP-78/08A patent/MEP7808A/xx unknown
- 1999-10-22 KR KR1020027005011A patent/KR100665598B1/ko not_active Expired - Fee Related
- 1999-10-22 CZ CZ20021384A patent/CZ299822B6/cs not_active IP Right Cessation
- 1999-10-22 UA UA2002054165A patent/UA73752C2/uk unknown
- 1999-10-22 CA CA002384283A patent/CA2384283C/en not_active Expired - Fee Related
- 1999-10-22 AT AT99955978T patent/ATE273961T1/de active
- 1999-10-22 CN CN2004101300014A patent/CN1896066B/zh not_active Expired - Lifetime
-
2000
- 2000-10-11 TW TW089121214A patent/TW553936B/zh not_active IP Right Cessation
-
2002
- 2002-03-08 ZA ZA200201961A patent/ZA200201961B/en unknown
- 2002-04-01 IN IN312MU2002 patent/IN2002MU00312A/en unknown
- 2002-04-15 IL IL149152A patent/IL149152A/en not_active IP Right Cessation
- 2002-04-17 BG BG106622A patent/BG65483B1/bg unknown
-
2003
- 2003-07-03 US US10/611,979 patent/US6881848B2/en not_active Expired - Fee Related
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