EP 2294058 A1 20110316 - 2-(BENZYLSULFONYL)-OXAZOLE DERIVATIVES, CHIRAL 2- (BENZYLSULFINYL) -OXAZOLE DERIVATIVES AND 2-(BENZYLSULFANYL)-OXAZOLE DERIVATIVES, METHODS FOR THE PRODUCTION THEREOF, AND USE THEREOF AS HERBICIDES AND PLANT GROWTH REGULATORS
Title (en)
2-(BENZYLSULFONYL)-OXAZOLE DERIVATIVES, CHIRAL 2- (BENZYLSULFINYL) -OXAZOLE DERIVATIVES AND 2-(BENZYLSULFANYL)-OXAZOLE DERIVATIVES, METHODS FOR THE PRODUCTION THEREOF, AND USE THEREOF AS HERBICIDES AND PLANT GROWTH REGULATORS
Title (de)
2-(BENZYLSULFONYL)-OXAZOL-DERIVATE, CHIRALE 2-(BENZYLSULFINYL)-OXAZOL-DERIVATE 2- (BENZYLSULFANYL) -OXAZOL-DERIVATE, VERFAHREN ZU DEREN HERSTELLUNG SOWIE DEREN VERWENDUNG ALS HERBIZIDE UND PFLANZENWACHSTUMSREGULATOREN
Title (fr)
DÉRIVÉS DE 2-(BENZYLSULFONYL)-OXAZOLE, DÉRIVÉS CHIRAUX DE 2-(BENZYLSULFINYL)-OXAZOLE, DÉRIVÉS DE 2- (BENZYLSULFANYL) -OXAZOLE, PROCÉDÉ POUR PRODUIRE CES DÉRIVÉS AINSI QUE LEUR UTILISATION COMME HERBICIDES ET RÉGULATEURS DE LA CROISSANCE DES PLANTES
Publication
Application
Priority
- EP 2009002741 W 20090415
- EP 08007743 A 20080422
- EP 09735369 A 20090415
Abstract (en)
[origin: EP2112143A1] 2-(Benzylsulfonyl)-oxazole-derivatives (I) and their salts are new. 2-(Benzylsulfonyl)-oxazole-derivatives of formula (I) and their salts are new. R 1>, R 2>e.g. (1-6C)-alkyl, (1-6C)-alkylcarbonyl, (1-6C)-alkylcarbonyl-(1-4C)-alkyl, (1-6C)-alkylcarbonyloxy, (1-6C)-alkoxy, (1-6C)-alkoxycarbonyl (all optionally substituted), H, halo, nitro, CN, formyl, C(O)OH, OH or amino; either R 9>, R 1> 0>e.g. H, (1-6C)-alkyl, (3-6C)-cycloalkyl or (1-6C)-haloalkyl; or R 9>R 1> 0>(1-6C)-alkylene, which optionally contains O, S, one or two amino or (1-6C)-alkyl amino groups; R 3>-R 7>e.g. (1-6C)-alkyl, (1-6C)-haloalkyl, (1-6C)-alkylcarbonyl, (1-6C)-haloalkylcarbonyl, (1-6C)-alkylcarbonyloxy or (1-6C)-haloalkylcarbonyloxy; and n : 0-2, preferably 1. Full Definitions are given in the DEFINITIONS (Full Definitions) Field. Independent claims are included for: (1) the preparation of (I); (2) the preparation of thioether compound of formula (II), comprising reacting 2-mercaptooxazole compound or an oxazol-2-(3H)-thione compound or its salt of formula (V), (Va), (Vb) or (Vc) with benzyl derivative of formula (VI) in the presence of an alkali or alkaline earth metal base or an organic base in a solvent; or reacting an oxazole derivative of formula (VII) with benzyl-imidothiocarbamate salt of formula (VIII), in stew procedure, in the presence of an aqueous alkali- or alkaline earth metal base or an alkali metal- or alkaline earth metal carbonate base and a solvent; or reacting (VII) with (VIII), in stew procedure, in the presence of an alkali or alkaline earth metal carbonate base and a solvent; or reacting (VII) with a benzyl-mercaptan compound of formula (IX) in the presence of an alkali- or alkaline earth metal base or organic base, optionally in a solvent, or halogenating or nitrating an oxazole derivative of formula (X) in a suitable solvent, or reacting an oxazole derivative of formula (XI), obtained from (V) by reacting with alkylating agent of formula (R 1> 2>Lg1), with a strong base and an alkylating agent of formula (R 1>Lg1) to obtain an oxazole compound of formula (XII), oxidizing (XII) to obtain oxazole compound (XIII) of formula (XIIIa) or (XIIIb), reacting (XIII) with (VIII) or (IX), or reacting benzyl disulfide derivative of formula (XV) with 2-amino-oxazole compound of formula (XIV) and a diazotizing agent; and (3) a composition comprising (I). Lg, Lg1 : a leaving group; and R 1> 2>(1-6C)-alkyl, which is optionally substituted by one or more halo. [Image] [Image] [Image] [Image] [Image] [Image] ACTIVITY : Plant Growth Regulant; Fungicide; Antibacterial; Virucide; Herbicide. MECHANISM OF ACTION : None given.
IPC 8 full level
C07D 263/46 (2006.01); C07D 413/12 (2006.01)
CPC (source: EP US)
C07D 263/46 (2013.01 - EP US); C07D 413/12 (2013.01 - EP US)
Citation (search report)
See references of WO 2009129953A1
Designated contracting state (EPC)
AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO SE SI SK TR
Designated extension state (EPC)
AL BA RS
DOCDB simple family (publication)
EP 2112143 A1 20091028; AU 2009240244 A1 20091029; BR PI0910489 A2 20190924; CA 2722214 A1 20091029; EP 2294058 A1 20110316; US 2011190125 A1 20110804; WO 2009129953 A1 20091029
DOCDB simple family (application)
EP 08007743 A 20080422; AU 2009240244 A 20090415; BR PI0910489 A 20090415; CA 2722214 A 20090415; EP 09735369 A 20090415; EP 2009002741 W 20090415; US 98905009 A 20090415