CN100400516C - 农药化合物的制备方法 - Google Patents
农药化合物的制备方法 Download PDFInfo
- Publication number
- CN100400516C CN100400516C CNB200510104171XA CN200510104171A CN100400516C CN 100400516 C CN100400516 C CN 100400516C CN B200510104171X A CNB200510104171X A CN B200510104171XA CN 200510104171 A CN200510104171 A CN 200510104171A CN 100400516 C CN100400516 C CN 100400516C
- Authority
- CN
- China
- Prior art keywords
- compound
- trifluoromethyl
- hydrogen
- general formula
- preparation
- 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.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 230000000361 pesticidal effect Effects 0.000 title description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical group 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 230000031709 bromination Effects 0.000 claims description 3
- 238000005893 bromination reaction Methods 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 230000026030 halogenation Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 4
- HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical group C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 150000003217 pyrazoles Chemical class 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000005899 Fipronil Substances 0.000 description 5
- 229940013764 fipronil Drugs 0.000 description 5
- 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 4
- 239000002904 solvent Substances 0.000 description 4
- 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
- 239000003905 agrochemical Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 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
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000003795 chemical substances by application 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
- -1 halide salts Chemical class 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NHNUFAASKXPOQA-UHFFFAOYSA-N (3-acetamido-2-hydroxyphenyl)arsonic acid Chemical compound C(C)(=O)NC=1C(=C(C=CC1)[As](O)(=O)O)O NHNUFAASKXPOQA-UHFFFAOYSA-N 0.000 description 1
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical class OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 1
- NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical class 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 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 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
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance 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
Claims (8)
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 |
---|---|---|---|
CNB01810522XA Division CN1244564C (zh) | 2000-06-09 | 2001-06-07 | 农药化合物的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1740162A CN1740162A (zh) | 2006-03-01 |
CN100400516C true CN100400516C (zh) | 2008-07-09 |
Family
ID=22784314
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB200510104171XA Expired - Fee Related CN100400516C (zh) | 2000-06-09 | 2001-06-07 | 农药化合物的制备方法 |
CNA2007100893143A Pending CN101062920A (zh) | 2000-06-09 | 2001-06-07 | 除虫化合物的制备方法及其新的中间体 |
CNB01810522XA Expired - Fee Related CN1244564C (zh) | 2000-06-09 | 2001-06-07 | 农药化合物的制备方法 |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNA2007100893143A Pending CN101062920A (zh) | 2000-06-09 | 2001-06-07 | 除虫化合物的制备方法及其新的中间体 |
CNB01810522XA Expired - Fee Related CN1244564C (zh) | 2000-06-09 | 2001-06-07 | 农药化合物的制备方法 |
Country Status (17)
Country | Link |
---|---|
US (1) | US7199246B2 (zh) |
EP (1) | EP1286969B1 (zh) |
JP (2) | JP4954425B2 (zh) |
KR (1) | KR100784935B1 (zh) |
CN (3) | CN100400516C (zh) |
AT (1) | ATE479661T1 (zh) |
AU (2) | AU2001276370B2 (zh) |
BR (1) | BR0111654A (zh) |
CA (1) | CA2407839C (zh) |
DE (1) | DE60142962D1 (zh) |
ES (1) | ES2347317T3 (zh) |
HU (1) | HUP0301672A3 (zh) |
IL (2) | IL152696A0 (zh) |
MX (1) | MXPA02012113A (zh) |
RU (2) | RU2291863C2 (zh) |
WO (1) | WO2001094315A2 (zh) |
ZA (2) | ZA200208986B (zh) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1642920B (zh) * | 2002-03-05 | 2010-05-26 | 拜尔作物科学股份有限公司 | 用作杀虫剂的5-取代-烷基氨基吡唑衍生物 |
US7517877B2 (en) * | 2002-03-05 | 2009-04-14 | Merial Limited | 5-substituted-alkylaminopyrazole derivatives as pesticides |
US9049860B2 (en) | 2013-04-17 | 2015-06-09 | The Hartz Mountain Corporation | Ectoparasiticidal methods |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0500209A1 (en) * | 1991-01-18 | 1992-08-26 | Rhone-Poulenc Agrochimie | Pesticidal 1-(2-pyridyl)pyrazoles |
WO2000035884A1 (en) * | 1998-12-11 | 2000-06-22 | Aventis Cropscience S.A. | Control of arthropods in animals |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2422400A (en) | 1944-04-07 | 1947-06-17 | Du Pont | Production of n-methylamides |
EP0024587B1 (en) * | 1979-08-22 | 1984-11-14 | Sandoz Ag | Propenylamines, processes for their production, pharmaceutical compositions containing them and their use as pharmaceuticals |
EP0215964B1 (en) | 1985-09-10 | 1991-01-23 | Kawaken Fine Chemicals Co., Ltd. | Process for preparing cyclic urea derivatives |
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 |
DE3719732A1 (de) * | 1987-06-12 | 1989-01-05 | Bayer Ag | Substituierte 5-methylamino-1-arylpyrazole |
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 |
US4966898A (en) * | 1989-08-15 | 1990-10-30 | Merrell Dow Pharmaceuticals Inc. | 4-substituted 17β-(cyclopropylamino)androst-5-en-3β-ol and related compounds useful as C17-20 lyase inhibitors |
US5556873A (en) | 1993-02-24 | 1996-09-17 | Rhone-Poulenc Inc. | Pesticidal 1-aryl-5-(substituted alkyl (thio) amido)pyrazoles |
BR9714181A (pt) * | 1996-12-24 | 2000-02-29 | Rhone Poulenc Agrochimie | Processo para controlar insetos por meio de aplicação de um ingrediente inseticidamente ativo, composições pesticida e afidicida, composto, e, processo para preparar o mesmo. |
-
2001
- 2001-06-07 CN CNB200510104171XA patent/CN100400516C/zh not_active Expired - Fee Related
- 2001-06-07 EP EP01953994A patent/EP1286969B1/en not_active Expired - Lifetime
- 2001-06-07 CN CNA2007100893143A patent/CN101062920A/zh active Pending
- 2001-06-07 AU AU2001276370A patent/AU2001276370B2/en not_active Ceased
- 2001-06-07 CN CNB01810522XA patent/CN1244564C/zh not_active Expired - Fee Related
- 2001-06-07 AT AT01953994T patent/ATE479661T1/de not_active IP Right Cessation
- 2001-06-07 JP JP2002501865A patent/JP4954425B2/ja not_active Expired - Lifetime
- 2001-06-07 MX MXPA02012113A patent/MXPA02012113A/es active IP Right Grant
- 2001-06-07 WO PCT/EP2001/007398 patent/WO2001094315A2/en active Application Filing
- 2001-06-07 CA CA002407839A patent/CA2407839C/en not_active Expired - Fee Related
- 2001-06-07 KR KR1020027016788A patent/KR100784935B1/ko not_active IP Right Cessation
- 2001-06-07 RU RU2002135674/04A patent/RU2291863C2/ru not_active IP Right Cessation
- 2001-06-07 IL IL15269601A patent/IL152696A0/xx active IP Right Grant
- 2001-06-07 HU HU0301672A patent/HUP0301672A3/hu unknown
- 2001-06-07 DE DE60142962T patent/DE60142962D1/de not_active Expired - Lifetime
- 2001-06-07 BR BR0111654-1A patent/BR0111654A/pt not_active IP Right Cessation
- 2001-06-07 RU RU2006129645/04A patent/RU2439061C2/ru not_active IP Right Cessation
- 2001-06-07 US US10/297,676 patent/US7199246B2/en not_active Expired - Lifetime
- 2001-06-07 AU AU7637001A patent/AU7637001A/xx active Pending
- 2001-06-07 ES ES01953994T patent/ES2347317T3/es 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
-
2012
- 2012-02-09 JP JP2012025809A patent/JP2012136525A/ja active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0500209A1 (en) * | 1991-01-18 | 1992-08-26 | Rhone-Poulenc Agrochimie | Pesticidal 1-(2-pyridyl)pyrazoles |
WO2000035884A1 (en) * | 1998-12-11 | 2000-06-22 | Aventis Cropscience S.A. | Control of arthropods in animals |
Also Published As
Publication number | Publication date |
---|---|
AU2001276370B2 (en) | 2006-08-03 |
EP1286969A2 (en) | 2003-03-05 |
EP1286969B1 (en) | 2010-09-01 |
MXPA02012113A (es) | 2003-04-25 |
ZA200209653B (en) | 2004-02-27 |
ES2347317T3 (es) | 2010-10-28 |
JP4954425B2 (ja) | 2012-06-13 |
RU2439061C2 (ru) | 2012-01-10 |
CN101062920A (zh) | 2007-10-31 |
JP2003535848A (ja) | 2003-12-02 |
ATE479661T1 (de) | 2010-09-15 |
WO2001094315A2 (en) | 2001-12-13 |
ZA200208986B (en) | 2003-11-04 |
BR0111654A (pt) | 2003-05-20 |
RU2291863C2 (ru) | 2007-01-20 |
IL152696A0 (en) | 2003-06-24 |
US20040058819A1 (en) | 2004-03-25 |
CN1244564C (zh) | 2006-03-08 |
CN1740162A (zh) | 2006-03-01 |
KR100784935B1 (ko) | 2007-12-17 |
CA2407839A1 (en) | 2001-12-13 |
CA2407839C (en) | 2009-09-08 |
CN1432002A (zh) | 2003-07-23 |
WO2001094315A3 (en) | 2002-04-18 |
KR20030007931A (ko) | 2003-01-23 |
IL152696A (en) | 2008-08-07 |
DE60142962D1 (de) | 2010-10-14 |
HUP0301672A3 (en) | 2005-01-28 |
RU2006129645A (ru) | 2008-02-27 |
JP2012136525A (ja) | 2012-07-19 |
US7199246B2 (en) | 2007-04-03 |
AU7637001A (en) | 2001-12-17 |
HUP0301672A2 (hu) | 2003-08-28 |
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C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: MERRIEARL CO., LTD. Free format text: FORMER OWNER: BAYER CROPSCIENCE SA Effective date: 20080627 |
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C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20080627 Address after: American Georgia Patentee after: Bayer Cropscience SA Address before: lyon Patentee before: Bayer Cropscience S. A. |
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CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20080709 Termination date: 20150607 |
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