ZA200501047B - Process for the preparation of phenyl pyrazole compounds - Google Patents

Process for the preparation of phenyl pyrazole compounds Download PDF

Info

Publication number: ZA200501047B
Authority: ZA; South Africa
Prior art keywords: compound; carried out; general formula; preparation; formula
Prior art date: 2002-07-05

Application number

ZA200501047A

Other languages

English (en)

Inventor

Jean-Erick Ancel

Joulle Vidal

Original Assignee

Nl Basf Agro B V Arnhem Wodens

Priority date (The priority date 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 date listed.)

2002-07-05

Filing date

2005-02-04

Publication date

2006-10-25

2005-02-04 Application filed by Nl Basf Agro B V Arnhem Wodens filed Critical Nl Basf Agro B V Arnhem Wodens

2006-10-25 Publication of ZA200501047B publication Critical patent/ZA200501047B/en

Links

238000000034 method Methods 0.000 title claims description 36
238000002360 preparation method Methods 0.000 title claims description 14
150000008048 phenylpyrazoles Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 52
239000002904 solvent Substances 0.000 claims description 13
238000006243 chemical reaction Methods 0.000 claims description 11
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 7
-1 aryl hydrazine Chemical compound 0.000 claims description 6
ZEHZNAXXOOYTJM-UHFFFAOYSA-N dicyanoacetylene Chemical group N#CC#CC#N ZEHZNAXXOOYTJM-UHFFFAOYSA-N 0.000 claims description 6
238000007254 oxidation reaction Methods 0.000 claims description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
230000003647 oxidation Effects 0.000 claims description 4
229910052709 silver Inorganic materials 0.000 claims description 4
239000004332 silver Substances 0.000 claims description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 2
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
235000004279 alanine Nutrition 0.000 claims description 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
229960001760 dimethyl sulfoxide Drugs 0.000 claims description 2
150000008282 halocarbons Chemical class 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
150000002978 peroxides Chemical class 0.000 claims description 2
239000002798 polar solvent Substances 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 claims description 2
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims 2
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 2
235000001258 Cinchona calisaya Nutrition 0.000 claims 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims 1
229960000948 quinine Drugs 0.000 claims 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000000543 intermediate Substances 0.000 description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
238000003818 flash chromatography Methods 0.000 description 4
238000000746 purification Methods 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
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 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
VUKNHTVKQVHRSS-UHFFFAOYSA-N 2-cyano-n-[2,6-dichloro-4-(trifluoromethyl)anilino]-2-(trifluoromethylsulfanyl)ethanimidoyl cyanide Chemical compound FC(F)(F)SC(C#N)C(C#N)=NNC1=C(Cl)C=C(C(F)(F)F)C=C1Cl VUKNHTVKQVHRSS-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
239000005899 Fipronil Substances 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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
230000008025 crystallization Effects 0.000 description 2
229940013764 fipronil Drugs 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
KYPOHTVBFVELTG-OWOJBTEDSA-N (e)-but-2-enedinitrile Chemical compound N#C\C=C\C#N KYPOHTVBFVELTG-OWOJBTEDSA-N 0.000 description 1
KYPOHTVBFVELTG-UPHRSURJSA-N (z)-but-2-enedinitrile Chemical compound N#C\C=C/C#N KYPOHTVBFVELTG-UPHRSURJSA-N 0.000 description 1
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
239000005708 Sodium hypochlorite Substances 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229960003280 cupric chloride Drugs 0.000 description 1
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 1
238000001914 filtration Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000007857 hydrazones Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229940101209 mercuric oxide Drugs 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
150000003217 pyrazoles Chemical class 0.000 description 1
150000004053 quinones Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 description 1
150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
238000005406 washing Methods 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
- C07D231/38—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/18—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by addition of thiols to unsaturated compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
- 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Catalysts (AREA)

ZA200501047A 2002-07-05 2005-02-04 Process for the preparation of phenyl pyrazole compounds ZA200501047B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP02356131A EP1378506B1 (fr)	2002-07-05	2002-07-05	Procédé de préparation de composés phényl-pyrazoles

Publications (1)

Publication Number	Publication Date
ZA200501047B true ZA200501047B (en)	2006-10-25

Family

ID=29719789

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200501047A ZA200501047B (en)	2002-07-05	2005-02-04	Process for the preparation of phenyl pyrazole compounds

Country Status (15)

Country	Link
US (2)	US7129372B2 (fr)
EP (1)	EP1378506B1 (fr)
JP (1)	JP4401957B2 (fr)
KR (1)	KR101011835B1 (fr)
CN (2)	CN100572361C (fr)
AU (1)	AU2003250177B2 (fr)
BR (1)	BR0312469B1 (fr)
CA (1)	CA2490987C (fr)
EA (1)	EA009069B1 (fr)
IL (1)	IL165895A (fr)
MX (1)	MXPA05000054A (fr)
PL (1)	PL212491B1 (fr)
UA (1)	UA79295C2 (fr)
WO (1)	WO2004005245A1 (fr)
ZA (1)	ZA200501047B (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1378506B1 (fr) *	2002-07-05	2006-07-26	BASF Agro B.V., Arnhem (NL), Wädenswil-Branch	Procédé de préparation de composés phényl-pyrazoles
US7667076B2 (en) *	2005-09-14	2010-02-23	Regents Of The University Of California	Amide forming chemical ligation
EP2443093B8 (fr) *	2009-03-16	2013-10-09	Basf Se	Procédé de préparation de dérivés de pyrazole
WO2014163932A1 (fr) *	2013-03-13	2014-10-09	Dow Agrosciences Llc	Préparation d'halo-alcoxy-aryl-hydrazines et d'intermédiaires dérivés de ceux-ci
US9212150B2 (en)	2013-03-13	2015-12-15	Dow Agrosciences Llc	Process for the preparation of certain triaryl pesticide intermediates
BR112016008070B8 (pt)	2013-10-17	2022-08-23	Dow Agrosciences Llc	Compostos pesticidas, e seus processos de preparação
WO2018125817A1 (fr)	2016-12-29	2018-07-05	Dow Agrosciences Llc	Procédés de préparation de composés pesticides

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL8202335A (nl) *	1982-06-09	1982-08-02	Single Buoy Moorings	Inrichting voor het op de plaats vasthouden van een lichaam met drijfvermogen ten opzichte van een ander lichaam.
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
US6638510B1 (en) *	1994-09-08	2003-10-28	Board Of Trustees Of Michigan State University	Recombinant plasmid and a method of controlling the effects of Yersinia pestis
US5814652A (en) *	1995-12-20	1998-09-29	Rhone-Poulenc Inc.	Pesticidal 5-amino-4-ethylsulfinyl-1-arylpyrazoles
WO1998039302A1 (fr) *	1997-03-03	1998-09-11	Rhone-Poulenc Agro	Procedes pour la preparation de produits intermediaires pesticides
EP1378506B1 (fr) *	2002-07-05	2006-07-26	BASF Agro B.V., Arnhem (NL), Wädenswil-Branch	Procédé de préparation de composés phényl-pyrazoles

2002
- 2002-07-05 EP EP02356131A patent/EP1378506B1/fr not_active Expired - Lifetime
2003
- 2003-06-30 EA EA200500158A patent/EA009069B1/ru not_active IP Right Cessation
- 2003-06-30 CN CNB2006101467308A patent/CN100572361C/zh not_active Expired - Fee Related
- 2003-06-30 US US10/519,823 patent/US7129372B2/en not_active Expired - Lifetime
- 2003-06-30 KR KR1020057000121A patent/KR101011835B1/ko not_active Expired - Lifetime
- 2003-06-30 MX MXPA05000054A patent/MXPA05000054A/es active IP Right Grant
- 2003-06-30 CA CA2490987A patent/CA2490987C/fr not_active Expired - Lifetime
- 2003-06-30 CN CNB038159961A patent/CN1317264C/zh not_active Expired - Fee Related
- 2003-06-30 WO PCT/EP2003/008212 patent/WO2004005245A1/fr not_active Ceased
- 2003-06-30 UA UAA200500957A patent/UA79295C2/uk unknown
- 2003-06-30 AU AU2003250177A patent/AU2003250177B2/en not_active Expired
- 2003-06-30 JP JP2004518774A patent/JP4401957B2/ja not_active Expired - Lifetime
- 2003-06-30 PL PL374842A patent/PL212491B1/pl unknown
- 2003-06-30 BR BRPI0312469-0A patent/BR0312469B1/pt active IP Right Grant
2004
- 2004-12-21 IL IL165895A patent/IL165895A/en active IP Right Grant
2005
- 2005-02-04 ZA ZA200501047A patent/ZA200501047B/en unknown
2006
- 2006-09-28 US US11/529,051 patent/US7323574B2/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
US7323574B2 (en)	2008-01-29
JP4401957B2 (ja)	2010-01-20
CN100572361C (zh)	2009-12-23
WO2004005245A1 (fr)	2004-01-15
EP1378506B1 (fr)	2006-07-26
PL212491B1 (pl)	2012-10-31
JP2005532384A (ja)	2005-10-27
AU2003250177A1 (en)	2004-01-23
CN1665781A (zh)	2005-09-07
PL374842A1 (en)	2005-11-14
UA79295C2 (en)	2007-06-11
EA009069B1 (ru)	2007-10-26
CA2490987A1 (fr)	2004-01-15
CA2490987C (fr)	2011-04-12
BR0312469B1 (pt)	2014-02-25
AU2003250177B2 (en)	2009-08-20
IL165895A (en)	2010-02-17
IL165895A0 (en)	2006-01-15
US7129372B2 (en)	2006-10-31
EP1378506A1 (fr)	2004-01-07
EA200500158A1 (ru)	2005-06-30
US20070021620A1 (en)	2007-01-25
CN1978432A (zh)	2007-06-13
BR0312469A (pt)	2005-05-03
CN1317264C (zh)	2007-05-23
US20060052614A1 (en)	2006-03-09
MXPA05000054A (es)	2005-12-05
KR20060052644A (ko)	2006-05-19
KR101011835B1 (ko)	2011-01-31

Publication	Publication Date	Title
EP1149082B1 (fr)	2006-02-08	Nouveau procede de preparation d'intermediaires pesticides
CN1103759C (zh)	2003-03-26	杀虫剂中间体的制备方法
CA2490987C (fr)	2011-04-12	Procede de production de composes de phhenyl-pyrazol
EP1073627B1 (fr)	2004-12-01	Procedes relatifs a la preparation d'intermediaires utiles dans l'elaboration des pesticides
EP1753726B1 (fr)	2010-01-06	Procede de preparation de derives de l'acide 1,5-diphenylpyrazole carboxylique
EP0952145B1 (fr)	2005-10-05	Procédé pour la préparation d'intermédiaires pesticides
JPH07247263A (ja)	1995-09-26	メチルチオベンゼン類の製造方法
EP0952144A1 (fr)	1999-10-27	Procédés pour la préparation d'intermédiaires pesticides