WO2001027092A3 - Process to prepare aryltriazolinones and novel intermediates thereto - Google Patents

Process to prepare aryltriazolinones and novel intermediates thereto Download PDF

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Publication number
WO2001027092A3
WO2001027092A3 PCT/US2000/028240 US0028240W WO0127092A3 WO 2001027092 A3 WO2001027092 A3 WO 2001027092A3 US 0028240 W US0028240 W US 0028240W WO 0127092 A3 WO0127092 A3 WO 0127092A3
Authority
WO
WIPO (PCT)
Prior art keywords
formula
hydrogen
aryltriazolinones
prepare
novel intermediates
Prior art date
Application number
PCT/US2000/028240
Other languages
French (fr)
Other versions
WO2001027092A2 (en
Inventor
Jaidev S Goudar
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 to AU10818/01A priority Critical patent/AU784318B2/en
Priority to HU0203543A priority patent/HU228358B1/en
Priority to DE60029245T priority patent/DE60029245T2/en
Priority to IL14906300A priority patent/IL149063A0/en
Priority to CNB008141355A priority patent/CN100349879C/en
Priority to EP00972109A priority patent/EP1240149B1/en
Application filed by Fmc Corp filed Critical Fmc Corp
Priority to JP2001530112A priority patent/JP4954409B2/en
Priority to BRPI0014561-0A priority patent/BR0014561B1/en
Publication of WO2001027092A2 publication Critical patent/WO2001027092A2/en
Publication of WO2001027092A3 publication Critical patent/WO2001027092A3/en
Priority to IL149063A priority patent/IL149063A/en
Priority to CY20061101428T priority patent/CY1106186T1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/22—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having nitrogen atoms of amidino groups further bound to nitrogen atoms, e.g. hydrazidines
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Pest Control & Pesticides (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Saccharide Compounds (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

A process is described for preparing 1-aryltriazolinones of formula (I) useful in the production of commercial herbicides, by: i) carbonylating an amidrazone of formula (A) with one or more carbonylating agent, or ii) condensing a hydrazonoyl derivative of formula (A) with one or more ring-forming agent in formula (A), where W, X, Y, Z, and R1 are fully described herein. Preferred are those where W is halogen or -NHR where R is hydrogen or haloalkyl; X and Y are independently selected from hydrogen, chloro, or fluoro; Z is hydrogen, bromo, iodo, nitro, amino, or methylsulfonylamino; and R1 is methyl. Certain compounds of formula (A) are novel compositions of matter. The process as described herein has utility in providing compounds of formula (I) in unexpectedly high yield and purity.
PCT/US2000/028240 1999-10-13 2000-10-12 Process to prepare aryltriazolinones and novel intermediates thereto WO2001027092A2 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
HU0203543A HU228358B1 (en) 1999-10-13 2000-10-12 Process to prepare aryltriazolinones and novel intermediates thereto
DE60029245T DE60029245T2 (en) 1999-10-13 2000-10-12 Process for the preparation of aryltriazolinones
IL14906300A IL149063A0 (en) 1999-10-13 2000-10-12 Process to prepare aryltriazolinones and novel intermediates thereto
CNB008141355A CN100349879C (en) 1999-10-13 2000-10-12 Process for preparing aryltriazolinones and novel intermediates thereto
EP00972109A EP1240149B1 (en) 1999-10-13 2000-10-12 Process to prepare aryltriazolinones
AU10818/01A AU784318B2 (en) 1999-10-13 2000-10-12 Process to prepare aryltriazolinones and novel intermediates thereto
JP2001530112A JP4954409B2 (en) 1999-10-13 2000-10-12 Process for producing aryltriazolinones and novel intermediates thereof
BRPI0014561-0A BR0014561B1 (en) 1999-10-13 2000-10-12 hydrazonoil derivative.
IL149063A IL149063A (en) 1999-10-13 2002-04-09 Process to prepare aryltriazolinones and novel intermediates thereto
CY20061101428T CY1106186T1 (en) 1999-10-13 2006-10-04 PREPARATION OF ARYLOTRIZOLINONES

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US15924799P 1999-10-13 1999-10-13
US60/159,247 1999-10-13
US09/663,336 US6492527B1 (en) 1999-10-13 2000-09-18 Process to prepare aryltriazolinones and novel intermediates thereto
US09/663,336 2000-09-18

Publications (2)

Publication Number Publication Date
WO2001027092A2 WO2001027092A2 (en) 2001-04-19
WO2001027092A3 true WO2001027092A3 (en) 2001-10-25

Family

ID=26855783

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2000/028240 WO2001027092A2 (en) 1999-10-13 2000-10-12 Process to prepare aryltriazolinones and novel intermediates thereto

Country Status (19)

Country Link
US (3) US6492527B1 (en)
EP (1) EP1240149B1 (en)
JP (1) JP4954409B2 (en)
KR (1) KR100722041B1 (en)
CN (1) CN100349879C (en)
AT (1) ATE332293T1 (en)
AU (1) AU784318B2 (en)
BR (1) BR0014561B1 (en)
CY (1) CY1106186T1 (en)
CZ (1) CZ304209B6 (en)
DE (1) DE60029245T2 (en)
DK (1) DK1240149T3 (en)
ES (1) ES2267577T3 (en)
HU (1) HU228358B1 (en)
IL (2) IL149063A0 (en)
PL (1) PL364879A1 (en)
PT (1) PT1240149E (en)
TW (1) TWI289140B (en)
WO (1) WO2001027092A2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5167283B2 (en) * 2008-01-10 2013-03-21 北興化学工業株式会社 Process for producing phenyltriazolinones
CN107043359B (en) * 2017-05-31 2019-08-09 江苏七洲绿色化工股份有限公司 A kind of preparation method of prothioconazoles intermediate
CN106986838B (en) * 2017-05-31 2019-11-15 江苏七洲绿色化工股份有限公司 A kind of preparation method of prothioconazoles
CN113072510A (en) * 2021-03-09 2021-07-06 浙江理工大学 Green preparation method of 1,2, 4-triazole-3-ketone compound

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US5449784A (en) * 1994-06-22 1995-09-12 Fmc Corporation Method of preparing aryl triazolinones with trialkyl orthoacetates

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NL7307000A (en) * 1972-05-26 1973-11-28
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US3786094A (en) * 1970-09-17 1974-01-15 Roussel Uclaf Novel phenylhydrazones
US3819703A (en) * 1971-03-23 1974-06-25 Bayer Ag Alpha-amino-alpha-acyl-carbonyl-phenyl-hydrazones
WO1986002642A1 (en) * 1984-10-31 1986-05-09 Fmc Corporation Herbicidal aryl triazolinones
JPH0291062A (en) * 1988-09-27 1990-03-30 Kumiai Chem Ind Co Ltd Triazole derivative and insecticide
EP0371438A2 (en) * 1988-11-29 1990-06-06 Warner-Lambert Company 3,5-Di-tertiary-butyl-4-hydroxyphenyl-1,3,4-thiadiazoles, and oxadiazoles and 3,5-di-tertiary-butyl-4-hydroxiphenyl- 1,2,4-thiadiazoles, -oxadiazoles as antiinflammatory agents
US5449784A (en) * 1994-06-22 1995-09-12 Fmc Corporation Method of preparing aryl triazolinones with trialkyl orthoacetates

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Also Published As

Publication number Publication date
HU228358B1 (en) 2013-03-28
CY1106186T1 (en) 2011-06-08
US6992221B2 (en) 2006-01-31
US20030036657A1 (en) 2003-02-20
JP4954409B2 (en) 2012-06-13
KR20020035171A (en) 2002-05-09
IL149063A0 (en) 2002-11-10
AU1081801A (en) 2001-04-23
CZ304209B6 (en) 2014-01-08
EP1240149A2 (en) 2002-09-18
ES2267577T3 (en) 2007-03-16
US20030144528A1 (en) 2003-07-31
PT1240149E (en) 2006-11-30
AU784318B2 (en) 2006-03-09
BR0014561A (en) 2003-07-29
PL364879A1 (en) 2004-12-27
CN1420874A (en) 2003-05-28
HUP0203543A3 (en) 2003-04-28
US6600049B2 (en) 2003-07-29
TWI289140B (en) 2007-11-01
DE60029245T2 (en) 2007-05-31
DE60029245D1 (en) 2006-08-17
BR0014561B1 (en) 2012-07-24
CZ20021240A3 (en) 2002-09-11
ATE332293T1 (en) 2006-07-15
KR100722041B1 (en) 2007-05-25
DK1240149T3 (en) 2006-10-30
EP1240149B1 (en) 2006-07-05
WO2001027092A2 (en) 2001-04-19
JP2004500341A (en) 2004-01-08
HUP0203543A2 (en) 2003-03-28
US6492527B1 (en) 2002-12-10
CN100349879C (en) 2007-11-21
IL149063A (en) 2007-05-15

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