AR017346A1 - PROCEDIMIENTO PARA LA PREPARACIoN DE UN HERBICIDA DE TRIAZOLINONA Y PROCEDIMIENTO PARA LA PREPARACIoN DE COMPUESTOS INTERMEDIARIOS. - Google Patents

PROCEDIMIENTO PARA LA PREPARACIoN DE UN HERBICIDA DE TRIAZOLINONA Y PROCEDIMIENTO PARA LA PREPARACIoN DE COMPUESTOS INTERMEDIARIOS.

Info

Publication number
AR017346A1
AR017346A1 ARP980105144A ARP980105144A AR017346A1 AR 017346 A1 AR017346 A1 AR 017346A1 AR P980105144 A ARP980105144 A AR P980105144A AR P980105144 A ARP980105144 A AR P980105144A AR 017346 A1 AR017346 A1 AR 017346A1
Authority
AR
Argentina
Prior art keywords
intermediary
formula
difluoromethyl
dihydro
oxo
Prior art date
Application number
ARP980105144A
Other languages
English (en)
Original Assignee
Fmc Corp
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.)
Filing date
Publication date
Priority claimed from US09/172,157 external-priority patent/US6077959A/en
Application filed by Fmc Corp filed Critical Fmc Corp
Publication of AR017346A1 publication Critical patent/AR017346A1/es

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/12—Oxygen or sulfur atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Procedimiento para preparar un herbicida de triazolinona (Compuesto E) de formula (I) donde X e Y son iguales o diferentes y son independientementeseleccionados entre halo, alquilo, cicloalquilo, alcoxi, nitro y heterocíclico y R es alquilo ohaloalq uilo de 1 a 10 átomos de carbono, que consiste encombinar el Intermediario D de la formula II, donde X, Y y R se definen como el Compuesto E, con aproximadamente 1 a aproximadamente 5 equivalentes molares(eq.M) de un ácido alcanoico,aproximadamente 1 a aproximadamente 9eq. M de hipoclorito de sodio y aproximadamente 1 a aproximadamente 5eq. M de una base,siendo las cantidades de todos los reactivos relativas a 1,0 eq.Mde Intermediario B de formula (III) donde Z es halo, con unalcanoato C de fo rmula IV dondeR es hidrogeno o -CH(CH3)OH, en presencia de un catalizador de paladio (II) y una amina R3N, en donde R es alquilo de 1 a 5 átomos de carbono. Elintermediario B es preparado por reaccion de un Intermediario A deformula (V) donde Z es h idrogeno o amino, con un agente halogenante en prsencia de un ácidofuerte. Un procedimiento para preparar alfa-2-dicloro-5-[4-(difluormetil-4,5-dihidro-3-metil-5-oxo-1H-1,2,4-triazol-1-il]-4-fluorbencenopropanoato de etilo(elHerbicida) consistente e n la reaccion de alfa-acetil-2-cloro-5-[4-(difluormetil)-4,5-dihidro-3-metil-5-oxo-1H-1,2,4-triazol-1-il]-4-fluorobencenopropanoatode etilo (Intermediario D), primeramente con hipoclorito de sodio y luego con una base,recuperando el Herbicida, siend o preparado dicho intermediario Dpor reaccion de 1-(4-cloro-2-fluor-5-bromo o 5-yodofenil-4-difluormetil-4,5-dihidro-3-metil-5-oxo-1H-1,2,4-triazol (Intermediario B) con 3-hidroxi-2-metilenbutanoato de etilo oacrilato de etilo en presencia de un cat alizador de paladio y una amina terciaria, siendo preparado dicho Intermediario B porreaccion de 1-(4-cloro-2-fluorfenil)-4-difluormetil-4-5-dihidro-3-metil-5-oxo-1H-1,2,4-triazol con un agente bromante oyodante en presencia de un ácido. Uncompuesto intermediario de formula VI, donde X es fluor, Y es cloro y Z es CH2CH[C(O)CH3]-CO2C2H5, bromo o yodo
ARP980105144A 1997-10-16 1998-10-16 PROCEDIMIENTO PARA LA PREPARACIoN DE UN HERBICIDA DE TRIAZOLINONA Y PROCEDIMIENTO PARA LA PREPARACIoN DE COMPUESTOS INTERMEDIARIOS. AR017346A1 (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US6227397P 1997-10-16 1997-10-16
US09/172,157 US6077959A (en) 1998-10-14 1998-10-14 Process for the preparation of a triazolinone herbicide

Publications (1)

Publication Number Publication Date
AR017346A1 true AR017346A1 (es) 2001-09-05

Family

ID=26742057

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP980105144A AR017346A1 (es) 1997-10-16 1998-10-16 PROCEDIMIENTO PARA LA PREPARACIoN DE UN HERBICIDA DE TRIAZOLINONA Y PROCEDIMIENTO PARA LA PREPARACIoN DE COMPUESTOS INTERMEDIARIOS.

Country Status (17)

Country Link
US (2) US6194583B1 (es)
EP (1) EP1036068B1 (es)
JP (1) JP2001519418A (es)
KR (1) KR100528761B1 (es)
CN (1) CN1159301C (es)
AR (1) AR017346A1 (es)
AT (1) ATE234292T1 (es)
AU (1) AU1095599A (es)
BR (1) BR9814927A (es)
CZ (1) CZ297607B6 (es)
DE (1) DE69812160T2 (es)
ES (1) ES2194361T3 (es)
HK (1) HK1032055A1 (es)
HU (1) HUP0003989A3 (es)
IL (1) IL135632A (es)
PL (1) PL342143A1 (es)
WO (1) WO1999019308A1 (es)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102174026B (zh) * 2011-03-11 2012-12-05 浙江省诸暨合力化学对外贸易有限公司 一种唑草酮的制备方法
CN103483280A (zh) * 2013-09-13 2014-01-01 南京工业大学 一种合成唑草酮酯的方法
CN104003949A (zh) * 2014-03-31 2014-08-27 济南先达化工科技有限公司 一种唑草酮的制备方法
US9856201B2 (en) 2014-06-04 2018-01-02 Monsanto Technology Llc 3,6-dichlorosalicylic acid compounds and related synthetic processes

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PT65179B (en) * 1975-06-09 1977-11-18 Takeda Chemical Industries Ltd Alpha/chlorocarboxylic acids
US5125958A (en) * 1988-08-31 1992-06-30 Fmc Corporation Herbicidal triazolinones
US5208212A (en) * 1988-08-31 1993-05-04 Fmc Corporation Herbicidal compositions containing triazolinones
CA1331463C (en) * 1988-08-31 1994-08-16 Kathleen Megan Poss Herbicidal triazolinones
ATE330471T1 (de) * 1995-08-21 2006-07-15 Fmc Corp Verfahren zur herstellung des herbizids alpha-2- dichloro-5- 4-(difluoromethyl)-4,5-dihydro-3- methyl-5-oxo-1h-1,2,4-triazol-1-ylö-4- fluorophenylpropansäureethylester
US5621112A (en) * 1996-07-18 1997-04-15 Fmc Corporation Process for the preparation of the herbicide ethyl α-2-dichloro-5-[4-(Difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-4-fluorobenzenepropanoate

Also Published As

Publication number Publication date
IL135632A (en) 2005-03-20
CZ297607B6 (cs) 2007-02-07
US6194583B1 (en) 2001-02-27
EP1036068A1 (en) 2000-09-20
US6268506B1 (en) 2001-07-31
DE69812160D1 (de) 2003-04-17
HUP0003989A2 (en) 2001-03-28
CN1280573A (zh) 2001-01-17
BR9814927A (pt) 2000-09-05
CZ20001325A3 (cs) 2000-09-13
DE69812160T2 (de) 2003-12-18
WO1999019308A1 (en) 1999-04-22
CN1159301C (zh) 2004-07-28
EP1036068B1 (en) 2003-03-12
ATE234292T1 (de) 2003-03-15
PL342143A1 (en) 2001-05-21
HK1032055A1 (en) 2001-07-06
JP2001519418A (ja) 2001-10-23
KR20010031099A (ko) 2001-04-16
KR100528761B1 (ko) 2005-11-15
ES2194361T3 (es) 2003-11-16
HUP0003989A3 (en) 2002-01-28
IL135632A0 (en) 2001-05-20
AU1095599A (en) 1999-05-03

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