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WO1997048668A3 - Preparation de 3-aryle-5-haloalkyl-pyrazoles substitues a activite herbicide - Google Patents

Preparation de 3-aryle-5-haloalkyl-pyrazoles substitues a activite herbicide Download PDF

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Publication number
WO1997048668A3
WO1997048668A3 PCT/US1997/010525 US9710525W WO9748668A3 WO 1997048668 A3 WO1997048668 A3 WO 1997048668A3 US 9710525 W US9710525 W US 9710525W WO 9748668 A3 WO9748668 A3 WO 9748668A3
Authority
WO
WIPO (PCT)
Prior art keywords
haloalkyl
pyrazoles
aryl
substituted
alkyl
Prior art date
Application number
PCT/US1997/010525
Other languages
English (en)
Other versions
WO1997048668A2 (fr
Inventor
Bruce C Hamper
Michael K Mao
Original Assignee
Monsanto Co
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 US08/667,256 external-priority patent/US5880290A/en
Priority claimed from US08/667,135 external-priority patent/US5869688A/en
Priority claimed from US08/667,103 external-priority patent/US5698708A/en
Priority to HU0104324A priority Critical patent/HUP0104324A3/hu
Priority to NZ333414A priority patent/NZ333414A/xx
Priority to JP10503274A priority patent/JP2000512656A/ja
Application filed by Monsanto Co filed Critical Monsanto Co
Priority to BR9710711A priority patent/BR9710711A/pt
Priority to EP97931231A priority patent/EP0923520A2/fr
Priority to PL97330718A priority patent/PL330718A1/xx
Priority to AU34919/97A priority patent/AU720882B2/en
Publication of WO1997048668A2 publication Critical patent/WO1997048668A2/fr
Publication of WO1997048668A3 publication Critical patent/WO1997048668A3/fr

Links

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
    • C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
    • 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
    • C07D231/16—Halogen atoms or nitro radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne des procédés de préparation de 3-aryle-5-haloalkyle-pyrazoles substitués, et spécifiquement de préparation d'esters alcoyliques C1-5 d'acides 5-[1-(alkyle C1-5)-4-halo-5-(haloalkyle C1-3)-1H-pyrazole-3-yl]-2,4-dihalo-benzoïques tels que isopropyl 5-[4-bromo-1-méthyl-5-(trifluorométhyl)-1H-pyrazole-3-yl]-2-chloro-4-fluorobenzoate. Les procédés décrits comprennent de nouvelles approches de formation de phényl-dicétones, de formation et d'alkylation de pyrazoles, de bromation de composés hétérocycliques, d'oxydation de composés benzéniques à substitution alkyle, et d'estérification d'acides carboxyliques. On peut combiner ces procédés afin de préparer des 3-aryle-5-haloalkyle pyrazoles ou alternativement les utiliser dans des sous-combinaisons ou individuellement pour préparer des intermédiaires ou d'autres composés utiles.
PCT/US1997/010525 1996-06-20 1997-06-16 Preparation de 3-aryle-5-haloalkyl-pyrazoles substitues a activite herbicide WO1997048668A2 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
AU34919/97A AU720882B2 (en) 1996-06-20 1997-06-16 Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity
PL97330718A PL330718A1 (en) 1996-06-20 1997-06-16 Method of obtaining substituted 3-aryl-5-halogenoalkyl pyrazoles exhibiting herbicidal activity
EP97931231A EP0923520A2 (fr) 1996-06-20 1997-06-16 Preparation de 3-aryle-5-haloalkyl-pyrazoles substitues a activite herbicide
NZ333414A NZ333414A (en) 1996-06-20 1997-06-16 Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity
JP10503274A JP2000512656A (ja) 1996-06-20 1997-06-16 除草剤活性を有する置換された３―アリール―５―ハロアルキル―ピラゾールの製法
HU0104324A HUP0104324A3 (en) 1996-06-20 1997-06-16 Preparation of substituted 3-aryl-5-halogenalkyl-pyrazoles having herbicidal activity
BR9710711A BR9710711A (pt) 1996-06-20 1997-06-16 Prepara-Æo de 3-aril-5-haloalquil-pirazÄis substitu¡dos tendo atividade herbicida

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US08/667,256 US5880290A (en) 1994-01-31 1996-06-20 Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity
US08/667,135 1996-06-20
US08/667,103 1996-06-20
US08/667,103 US5698708A (en) 1996-06-20 1996-06-20 Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity
US08/667,135 US5869688A (en) 1994-07-20 1996-06-20 Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity
US08/667,256 1996-06-20

Publications (2)

Publication Number Publication Date
WO1997048668A2 WO1997048668A2 (fr) 1997-12-24
WO1997048668A3 true WO1997048668A3 (fr) 1998-04-02

Family

ID=27418163

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1997/010525 WO1997048668A2 (fr) 1996-06-20 1997-06-16 Preparation de 3-aryle-5-haloalkyl-pyrazoles substitues a activite herbicide

Country Status (10)

Country Link
EP (1) EP0923520A2 (fr)
JP (1) JP2000512656A (fr)
CN (1) CN1228075A (fr)
AU (1) AU720882B2 (fr)
BR (1) BR9710711A (fr)
CA (1) CA2258215A1 (fr)
HU (1) HUP0104324A3 (fr)
NZ (1) NZ333414A (fr)
PL (1) PL330718A1 (fr)
WO (1) WO1997048668A2 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5532416A (en) * 1994-07-20 1996-07-02 Monsanto Company Benzoyl derivatives and synthesis thereof
AU1445001A (en) * 1999-10-29 2001-05-14 Boehringer Ingelheim Pharmaceuticals, Inc. Process of making substituted pyrazoles
DK2999694T3 (en) * 2013-05-22 2017-06-19 Bayer Cropscience Ag PROCEDURE FOR PREPARING 3,5-BIS (FLUORAL COOL) PYRAZOLD DERIVATIVES FROM ALFA, ALFA DIHALOGENAMINES
CN114874144B (zh) * 2022-03-28 2024-07-05 曲靖师范学院 一种制备4-溴代n-芳基吡唑类化合物的工艺

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2578654A (en) * 1950-01-28 1951-12-18 Shell Dev Preparation of tertiary-alkyl-substituted benzene carboxylic acids
US3426035A (en) * 1966-02-03 1969-02-04 Dow Chemical Co Halogenation of aromatic compounds
GB1147346A (en) * 1965-11-09 1969-04-02 Inst Francais Du Petrole Process for oxidation of paraxylene
EP0020964A1 (fr) * 1979-06-02 1981-01-07 BASF Aktiengesellschaft Procédé de synthèse de pyrazoles
EP0317275A2 (fr) * 1987-11-20 1989-05-24 British Technology Group Usa Inc. Contrôle d'ectoparasites
WO1992006962A1 (fr) * 1990-10-18 1992-04-30 Monsanto Company Composes herbicides d'haloalkylpyrazoles aryle substitue
JPH072798A (ja) * 1993-06-17 1995-01-06 Sumika Fine Chem Kk ５−ハロゲノピリミジン誘導体の製造方法
WO1996002515A1 (fr) * 1994-07-20 1996-02-01 Monsanto Company Acides benzoiques a substitution heterocyclique et carbocyclique et synthese de ces derniers
WO1996002486A1 (fr) * 1994-07-20 1996-02-01 Monsanto Company Derives de benzoyle et leur synthese

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2578654A (en) * 1950-01-28 1951-12-18 Shell Dev Preparation of tertiary-alkyl-substituted benzene carboxylic acids
GB1147346A (en) * 1965-11-09 1969-04-02 Inst Francais Du Petrole Process for oxidation of paraxylene
US3426035A (en) * 1966-02-03 1969-02-04 Dow Chemical Co Halogenation of aromatic compounds
EP0020964A1 (fr) * 1979-06-02 1981-01-07 BASF Aktiengesellschaft Procédé de synthèse de pyrazoles
EP0317275A2 (fr) * 1987-11-20 1989-05-24 British Technology Group Usa Inc. Contrôle d'ectoparasites
WO1992006962A1 (fr) * 1990-10-18 1992-04-30 Monsanto Company Composes herbicides d'haloalkylpyrazoles aryle substitue
JPH072798A (ja) * 1993-06-17 1995-01-06 Sumika Fine Chem Kk ５−ハロゲノピリミジン誘導体の製造方法
WO1996002515A1 (fr) * 1994-07-20 1996-02-01 Monsanto Company Acides benzoiques a substitution heterocyclique et carbocyclique et synthese de ces derniers
WO1996002486A1 (fr) * 1994-07-20 1996-02-01 Monsanto Company Derives de benzoyle et leur synthese

Non-Patent Citations (14)

* Cited by examiner, † Cited by third party
Title
A.R. KATRIZKY: "Advances in Heteocyclic Chemistry, vol. 57, see the chapter: "Halogenation of Heterocycles: I. Five-Membered Rings"", 1993, ACADEMIC PRESS, INC., SAN DIEGO, XP002054159 *
B.A. KELLOG ET AL.: "Base Catalyzed Hydrolysis and 18O=C Exchange of Ethyl and Isopropyl Toluoate in H2O and D2O Media. The Anionic Tetrahedral Intermediates Are Protonically Equilibrated", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 117, no. 6, 15 February 1995 (1995-02-15), DC US, pages 1731 - 1735, XP002054157 *
CHEMICAL ABSTRACTS, vol. 109, no. 25, 19 December 1988, Columbus, Ohio, US; abstract no. 230773c, Y. AHMAD ET AL.: "A modified preparative method for 5,7-dibromo-8-hydroxy- quinoline." page 836; column 2; XP002054163 *
CHEMICAL ABSTRACTS, vol. 92, no. 7, 18 February 1980, Columbus, Ohio, US; abstract no. 57881s, V.V. BRILEV ET AL.: "Oxidation of 2,4-dichlorotoluene by molecular oxygen in the presence of a cobalt bromide catalyst." page 598; XP002054164 *
DATABASE WPI Section Ch Week 9511, Derwent World Patents Index; Class E13, AN 95-078002, XP002054165 *
HOUBEN-WEYL: "Methoden der Organischen Chemie, vol. E5: "Carbonsäuren und Carbonsäure-Derivate"", 1985, GEORG THIEME VERLAG, STUTTGART, XP002054162 *
J.I. TRUJILLO ET AL.: "Facile Esterification of Sulfonic Acids and Carboxylic Acids with Triethylorthoactetate", TETRAHEDRON LETTERS., vol. 34, no. 46, 12 November 1993 (1993-11-12), OXFORD GB, pages 7355 - 7358, XP002054158 *
L.F FIESER ET AL.: "Reagents for Organic Synthesis", 1967, JOHN WILEY AND SONS, INC., NEW YORK, XP002054160 *
PAK. J. SCI. IND. RES., vol. 31, no. 5, 1988, pages 380 *
S. PATAI: "The chemistry of acyl halides in "The Chemistry of Functional Groups", chapter 6: "Mechanisms of substitution at the COX group"", 1972, INTERSCIENCE PUBLISHERS, LONDON, XP002054161 *
T. ITAHARA ET AL.: "Chloroperoxidase Catalyzed Halogenation of Pyrimidine Bases", CHEMISTRY LETTERS., no. 12, 1987, TOKYO JP, pages 2311 - 2312, XP002054156 *
T.K. CHEN ET AL.: "A Convinient Synthesis of 2,3,5,6-Tetrahalogenopyridines and of 3,5-Bis(alkylthio)pyridines from 2,6-Diaminopyridine", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS., no. 23, 1980, LETCHWORTH GB, pages 1139 - 1140, XP002054154 *
VESTSI AKAD. NAVUK BSSR, SER. KHIM. NAVUK, no. 5, 1979, pages 33 - 37 *
Y.L. GOL'DFARB ET AL.: "New Method for Preparation of 2-Bromothiophene", BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR. DIVISION OF CHEMICAL SCIENCE., vol. 31, no. 10(2), October 1982 (1982-10-01), NEW YORK US, pages 2104 - 2105, XP002054155 *

Also Published As

Publication number Publication date
AU720882B2 (en) 2000-06-15
HUP0104324A2 (hu) 2002-02-28
NZ333414A (en) 2000-05-26
AU3491997A (en) 1998-01-07
PL330718A1 (en) 1999-05-24
CA2258215A1 (fr) 1997-12-24
HUP0104324A3 (en) 2002-04-29
BR9710711A (pt) 1999-08-17
CN1228075A (zh) 1999-09-08
EP0923520A2 (fr) 1999-06-23
JP2000512656A (ja) 2000-09-26
WO1997048668A2 (fr) 1997-12-24

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