Title:
イソオキサゾリン-3-イルアシルベンゼンの製造方法
Document Type and Number:
Japanese Patent JP4786032
Kind Code:
B2
Abstract:
3-(2-Alkylthio-5-acylphenyl)-isoxazoles (I) are prepared by a multi-stage process via 3-(2-aminophenyl)-isoxazole intermediates (VI). Also new are various oxime and isoxazole derivative intermediates, including (VI); and methods for preparing oximes (XV) and thioethers (XIX) . Preparation of 3-(2-alkylthio-5-acylphenyl)-isoxazoles of formula (I) involves preparing a 3-(2-aminophenyl)-isoxazole intermediate of formula (VI), then halogenating, thioalkylating, oxidizing and acylating to give (I). [Image] R 1, R 3-R 5 : H or 1-6C alkyl; or R 4+R 5 : a bond; R 2 : 1-6C alkyl; R 6 : heterocycle; n : 0-2. Independent claims are included for: (i) new oxime and isoxazole derivative intermediates of formulae (III), (X) (including (VI)) and (XII); (ii) the preparation of benzaldoxime derivatives of formula (XV), involving the reaction of toluene derivatives of formula (XVI) with an organic nitrite of formula R-ONO in presence of a base, where the process optionally further includes the conversion of the oxime group of (XV) into aldehyde, nitrile or nitrile oxide; (iii) the preparation of thioethers of formula (XIX), involving the reaction of an aniline of formula (XX) with a dialkylsulfide of formula R 2SSR 2 (VII) in presence of a catalyst; and (iv) new benzaldoxime compounds of formula (XV'). [Image] [Image] A : NO 2, NH 2 or SR 2; X : NO 2 or SO 2R y; R x, R y : inert substituents; m : 0-4; p : 0-5; R' 1 : H, 1-6C alkyl, halo, 1-6C alkoxy or 1-6C alkylthio; X' : S(O) nR' y; R' y : H, Cl or Br '' in the para position of the phenyl ring to X' '' (sic). ACTIVITY : Herbicidal. MECHANISM OF ACTION : None given.
Inventors:
Reinheimer, Yoahim
Fondayne, Wolfgang
Gebhart, Joachim
Rack, michael
Rohtomann, René
Getz, norbert
Kyle, Michael
Witchell, Matthias
Hagen, Helmut
Misritz, Wolf
Baumann, Ernst
Fondayne, Wolfgang
Gebhart, Joachim
Rack, michael
Rohtomann, René
Getz, norbert
Kyle, Michael
Witchell, Matthias
Hagen, Helmut
Misritz, Wolf
Baumann, Ernst
Application Number:
JP2000548313A
Publication Date:
October 05, 2011
Filing Date:
May 04, 1999
Export Citation:
Assignee:
BASF SE
International Classes:
C07D261/04; C07C201/12; C07C205/44; C07C249/06; C07C251/48; C07C251/52; C07C253/00; C07C317/32; C07C319/14; C07D261/02; C07D261/08; C07D413/02; C07D413/10; C07C255/50; C07C323/09; C07C; C07D
Domestic Patent References:
| JP2002529540A | 2002-09-10 |
Foreign References:
| WO1997038996A1 | 1997-10-23 | |||
| WO1997041105A1 | 1997-11-06 | |||
| WO1996026200A1 | 1996-08-29 | |||
| WO1996026206A1 | 1996-08-29 | |||
| DE107095C | 1899-10-31 | |||
| WO1998031681A1 | 1998-07-23 |
Attorney, Agent or Firm:
Satoshi Eto