JP2012136525A - 農薬化合物の調製方法 - Google Patents
農薬化合物の調製方法 Download PDFInfo
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- JP2012136525A JP2012136525A JP2012025809A JP2012025809A JP2012136525A JP 2012136525 A JP2012136525 A JP 2012136525A JP 2012025809 A JP2012025809 A JP 2012025809A JP 2012025809 A JP2012025809 A JP 2012025809A JP 2012136525 A JP2012136525 A JP 2012136525A
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- Prior art keywords
- compound
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- trifluoromethylsulfinylpyrazole
- dichloro
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 230000000361 pesticidal effect Effects 0.000 title description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- -1 tetraalkylammonium halide Chemical class 0.000 claims description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- 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 claims description 6
- 239000005899 Fipronil Substances 0.000 claims description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 229940013764 fipronil Drugs 0.000 claims description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- ZIRACHWTQPZPFW-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(hydroxymethylamino)-4-(trifluoromethylsulfinyl)pyrazole-3-carbonitrile Chemical compound OCNC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZIRACHWTQPZPFW-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- BKDCZXGMFJWELE-UHFFFAOYSA-N methyl n-[5-cyano-2-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrazol-3-yl]methanimidate Chemical compound COC=NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl BKDCZXGMFJWELE-UHFFFAOYSA-N 0.000 claims description 3
- 239000012279 sodium borohydride Substances 0.000 claims description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000575 pesticide Substances 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000003217 pyrazoles Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RRXZEWZJQKBZCP-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(methylamino)-4-(trifluoromethylsulfinyl)pyrazole-3-carbonitrile Chemical compound CNC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl RRXZEWZJQKBZCP-UHFFFAOYSA-N 0.000 description 1
- ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- YJRNJPKBDSEHLR-UHFFFAOYSA-N n-[5-cyano-2-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrazol-3-yl]-n-methylformamide Chemical compound O=CN(C)C1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl YJRNJPKBDSEHLR-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Description
R1はCNまたはCSNH2であり;
R2は水素または塩化物であり;
R3は、ハロゲンまたはハロアルキルまたはハロアルコキシまたはSF5である]
の化合物を調製する方法を提供し、当該方法は、化学式(II)
3−シアノ−1−(2,6−ジクロロ−4−トリフルオロメチルフェニル)−5−N−ホルミル−N−メチルアミノ−4−トリフルオロメチルスルフィニルピラゾール(化合物II);
3−シアノ−1−(2,6−ジクロロ−4−トリフルオロメチルフェニル)−5−メトキシメチリデンアミノ−4−トリフルオロメチルスルフィニルピラゾール(化合物III)。
R1はCNまたはCSNH2であり;
XはNまたはCR4であり;
R2およびR4は、それぞれ独立的に、水素または塩素であり;
R3は、ハロゲン、ハロアルキル、ハロアルコキシまたは−SF5であり;
R5およびR6は、それぞれ独立的に、アルキル基であり;
nは、0、1、または2である]
により定義され、農薬特性を有することが知られている更なる重要なピラゾールの出発材料として使用することができる。
実質的にモル過剰量のオルトギ酸トリメチルを、0.5当量のパラトルエンスルホン酸と共に、還流下でフィプロニル(化合物IV)と反応させることにより、3−シアノ−1−(2,6−ジクロロ−4−トリフルオロメチルフェニル)−5−メトキシメチリデンアミノ−4−トリフルオロメチルスルフィニルピラゾール(化合物III)が得られる。
3mLのメタノール中における0.437gのフィプロニル(Fipronil)と1.4当量のパラホルムアルデヒドの懸濁液に5当量のナトリウムメチラート(メタノール中における30%溶液)を急速に加えることにより、20℃で3時間および60℃で1時間の後、3−シアノ−1−(2,6−ジクロロ−4−トリフルオロメチルフェニル)−5−ヒドロキシメチルアミノ−4−トリフルオロメチルスルフィニルピラゾール(化合物V)を得た。次いで、この媒質に1当量のホウ水素化ナトリウムを加えた後、古典的な抽出とクロマトグラフィーによる分離を行うことにより、3−シアノ−1−(2,6−ジクロロ−4−トリフルオロメチルフェニル)−5−メチルアミノ−4−トリフルオロメチルスルフィニルピラゾール(化合物I)を得た。
R1はCNまたはCSNH2であり;
R2は水素または塩素であり;
R3は、ハロゲンまたはハロアルキルまたはハロアルコキシまたはSF5である]
の化合物を調製する方法を提供し、当該方法は、化学式(II)
Claims (17)
- R1がCNであり、R2が塩化物であり、R3がトリフルオロメチルである、請求項1に記載の方法。
- 前記プロトン源が酸性水溶液である、請求項1または2に記載の方法。
- 前記酸性水溶液が塩化水素水溶液である、請求項3に記載の方法。
- 溶媒の存在下で実施される、請求項1〜4のいずれか一項に記載の方法。
- 前記溶媒がトルエンまたはキシレンである、請求項5に記載の方法。
- 前記第四級アンモニウム塩がハロゲン化テトラアルキルアンモニウムである、請求項7に記載の方法。
- 前記ハロゲン化テトラアルキルアンモニウムが臭化テトラアルキルアンモニウムである、請求項7または8に記載の方法。
- 有機溶媒の存在下で実施される、請求項7〜9のいずれか一項に記載の方法。
- 前記溶媒がトルエンまたはキシレンである、請求項10に記載の方法。
- 請求項1で定義されている化合物(I)を調製する方法であって、請求項6で定義されている化合物(III)を第四級アンモニウム塩と反応させ、続いて、酸を付加することを含む、調製方法。
- 前記還元剤がホウ水素化ナトリウムである、請求項13に記載の方法。
- 新規の化合物、3−シアノ−1−(2,6−ジクロロ−4−トリフルオロメチルフェニル)−5−N−ホルミル−N−メチルアミノ−4−トリフルオロメチルスルフィニルピラゾール。
- 新規の化合物、3−シアノ−1−(2,6−ジクロロ−4−トリフルオロメチルフェニル)−5−メトキシメチリデンアミノ−4−トリフルオロメチルスルフィニルピラゾール。
- 新規の化合物、3−シアノ−1−(2,6−ジクロロ−4−トリフルオロメチルフェニル)−5−ヒドロキシメチルアミノ−4−トリフルオロメチルスルフィニルピラゾール。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US21080300P | 2000-06-09 | 2000-06-09 | |
US60/210,803 | 2000-06-09 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2002501865A Division JP4954425B2 (ja) | 2000-06-09 | 2001-06-07 | 農薬化合物の調製方法 |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2012136525A true JP2012136525A (ja) | 2012-07-19 |
Family
ID=22784314
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2002501865A Expired - Lifetime JP4954425B2 (ja) | 2000-06-09 | 2001-06-07 | 農薬化合物の調製方法 |
JP2012025809A Pending JP2012136525A (ja) | 2000-06-09 | 2012-02-09 | 農薬化合物の調製方法 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2002501865A Expired - Lifetime JP4954425B2 (ja) | 2000-06-09 | 2001-06-07 | 農薬化合物の調製方法 |
Country Status (17)
Country | Link |
---|---|
US (1) | US7199246B2 (ja) |
EP (1) | EP1286969B1 (ja) |
JP (2) | JP4954425B2 (ja) |
KR (1) | KR100784935B1 (ja) |
CN (3) | CN100400516C (ja) |
AT (1) | ATE479661T1 (ja) |
AU (2) | AU2001276370B2 (ja) |
BR (1) | BR0111654A (ja) |
CA (1) | CA2407839C (ja) |
DE (1) | DE60142962D1 (ja) |
ES (1) | ES2347317T3 (ja) |
HU (1) | HUP0301672A3 (ja) |
IL (2) | IL152696A0 (ja) |
MX (1) | MXPA02012113A (ja) |
RU (2) | RU2439061C2 (ja) |
WO (1) | WO2001094315A2 (ja) |
ZA (2) | ZA200208986B (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL163790A0 (en) * | 2002-03-05 | 2005-12-18 | Bayer Cropscience Sa | 5-Substituted-alkylaminopyrazole derivatives as pesticides |
ES2274210T3 (es) * | 2002-03-05 | 2007-05-16 | Merial Limited | Alquilamino-pirazoles sustituidos en la posicion 5 como pesticidas. |
US9049860B2 (en) | 2013-04-17 | 2015-06-09 | The Hartz Mountain Corporation | Ectoparasiticidal methods |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63310871A (ja) * | 1987-06-12 | 1988-12-19 | バイエル・アクチエンゲゼルシヤフト | 置換された5−メチルアミノ−1−アリールピラゾール類 |
JPS63313753A (ja) * | 1979-08-22 | 1988-12-21 | サンド・アクチエンゲゼルシヤフト | プロペニルアミン類、その製造法、これを含む薬剤組成物および医薬としてのその用途 |
JPS63316771A (ja) * | 1987-06-12 | 1988-12-26 | ローヌ―プーラン・アグリカルチヤー・リミテツド | N−フェニルピラゾール誘導体 |
JPH0283376A (ja) * | 1988-09-19 | 1990-03-23 | Pfizer Pharmaceut Co Ltd | ベンゾオキサゾロン誘導体および抗アレルギー又は抗炎症組成物 |
JPH0383998A (ja) * | 1989-08-15 | 1991-04-09 | Merrell Dow Pharmaceut Inc | C17‐20リアーゼ阻害剤として有用な4‐置換17β‐(シクロプロピルアミノ)アンドロスト‐5‐エン‐3β‐オール及び関連化合物類 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2422400A (en) * | 1944-04-07 | 1947-06-17 | Du Pont | Production of n-methylamides |
DE3581541D1 (de) * | 1985-09-10 | 1991-02-28 | Kawaken Fine Chemicals Co | Verfahren zur herstellung von zyklischen urea-derivaten. |
US5232940A (en) | 1985-12-20 | 1993-08-03 | Hatton Leslie R | Derivatives of N-phenylpyrazoles |
NO179282C (no) * | 1991-01-18 | 1996-09-11 | Rhone Poulenc Agrochimie | Nye 1-(2-pyridyl)pyrazolforbindelser til kontroll av skadeinsekter |
US5556873A (en) | 1993-02-24 | 1996-09-17 | Rhone-Poulenc Inc. | Pesticidal 1-aryl-5-(substituted alkyl (thio) amido)pyrazoles |
CA2275635C (en) * | 1996-12-24 | 2008-11-25 | Rhone-Poulenc Agrochimie | Pesticidal 1-arylpyrazoles |
AR021608A1 (es) | 1998-12-11 | 2002-07-31 | Merial Ltd | Represion de artropodos en animales |
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2001
- 2001-06-07 BR BR0111654-1A patent/BR0111654A/pt not_active IP Right Cessation
- 2001-06-07 CN CNB200510104171XA patent/CN100400516C/zh not_active Expired - Fee Related
- 2001-06-07 HU HU0301672A patent/HUP0301672A3/hu unknown
- 2001-06-07 US US10/297,676 patent/US7199246B2/en not_active Expired - Lifetime
- 2001-06-07 WO PCT/EP2001/007398 patent/WO2001094315A2/en active Application Filing
- 2001-06-07 CN CNA2007100893143A patent/CN101062920A/zh active Pending
- 2001-06-07 CN CNB01810522XA patent/CN1244564C/zh not_active Expired - Fee Related
- 2001-06-07 CA CA002407839A patent/CA2407839C/en not_active Expired - Fee Related
- 2001-06-07 AU AU2001276370A patent/AU2001276370B2/en not_active Ceased
- 2001-06-07 DE DE60142962T patent/DE60142962D1/de not_active Expired - Lifetime
- 2001-06-07 RU RU2006129645/04A patent/RU2439061C2/ru not_active IP Right Cessation
- 2001-06-07 JP JP2002501865A patent/JP4954425B2/ja not_active Expired - Lifetime
- 2001-06-07 AU AU7637001A patent/AU7637001A/xx active Pending
- 2001-06-07 IL IL15269601A patent/IL152696A0/xx active IP Right Grant
- 2001-06-07 AT AT01953994T patent/ATE479661T1/de not_active IP Right Cessation
- 2001-06-07 MX MXPA02012113A patent/MXPA02012113A/es active IP Right Grant
- 2001-06-07 RU RU2002135674/04A patent/RU2291863C2/ru not_active IP Right Cessation
- 2001-06-07 ES ES01953994T patent/ES2347317T3/es not_active Expired - Lifetime
- 2001-06-07 KR KR1020027016788A patent/KR100784935B1/ko not_active IP Right Cessation
- 2001-06-07 EP EP01953994A patent/EP1286969B1/en not_active Expired - Lifetime
-
2002
- 2002-11-05 ZA ZA200208986A patent/ZA200208986B/xx unknown
- 2002-11-07 IL IL152696A patent/IL152696A/en not_active IP Right Cessation
- 2002-11-27 ZA ZA200209653A patent/ZA200209653B/en unknown
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2012
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63313753A (ja) * | 1979-08-22 | 1988-12-21 | サンド・アクチエンゲゼルシヤフト | プロペニルアミン類、その製造法、これを含む薬剤組成物および医薬としてのその用途 |
JPS63310871A (ja) * | 1987-06-12 | 1988-12-19 | バイエル・アクチエンゲゼルシヤフト | 置換された5−メチルアミノ−1−アリールピラゾール類 |
JPS63316771A (ja) * | 1987-06-12 | 1988-12-26 | ローヌ―プーラン・アグリカルチヤー・リミテツド | N−フェニルピラゾール誘導体 |
JPH0283376A (ja) * | 1988-09-19 | 1990-03-23 | Pfizer Pharmaceut Co Ltd | ベンゾオキサゾロン誘導体および抗アレルギー又は抗炎症組成物 |
JPH0383998A (ja) * | 1989-08-15 | 1991-04-09 | Merrell Dow Pharmaceut Inc | C17‐20リアーゼ阻害剤として有用な4‐置換17β‐(シクロプロピルアミノ)アンドロスト‐5‐エン‐3β‐オール及び関連化合物類 |
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JP2003535848A (ja) | 2003-12-02 |
AU2001276370B2 (en) | 2006-08-03 |
US20040058819A1 (en) | 2004-03-25 |
IL152696A (en) | 2008-08-07 |
JP4954425B2 (ja) | 2012-06-13 |
RU2006129645A (ru) | 2008-02-27 |
RU2291863C2 (ru) | 2007-01-20 |
KR100784935B1 (ko) | 2007-12-17 |
BR0111654A (pt) | 2003-05-20 |
CA2407839C (en) | 2009-09-08 |
ES2347317T3 (es) | 2010-10-28 |
CN1740162A (zh) | 2006-03-01 |
US7199246B2 (en) | 2007-04-03 |
CN100400516C (zh) | 2008-07-09 |
CN101062920A (zh) | 2007-10-31 |
ZA200208986B (en) | 2003-11-04 |
EP1286969A2 (en) | 2003-03-05 |
ZA200209653B (en) | 2004-02-27 |
RU2439061C2 (ru) | 2012-01-10 |
ATE479661T1 (de) | 2010-09-15 |
DE60142962D1 (de) | 2010-10-14 |
KR20030007931A (ko) | 2003-01-23 |
AU7637001A (en) | 2001-12-17 |
CA2407839A1 (en) | 2001-12-13 |
HUP0301672A3 (en) | 2005-01-28 |
CN1432002A (zh) | 2003-07-23 |
CN1244564C (zh) | 2006-03-08 |
IL152696A0 (en) | 2003-06-24 |
EP1286969B1 (en) | 2010-09-01 |
WO2001094315A3 (en) | 2002-04-18 |
WO2001094315A2 (en) | 2001-12-13 |
MXPA02012113A (es) | 2003-04-25 |
HUP0301672A2 (hu) | 2003-08-28 |
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