Patent DE-10025830-A1 (DE)
Title: New 4-acyl-2,3-dihydro-benzofuran or -benzothiophene derivatives, useful as pre- or post-emergence, total or selective herbicides or as plant growth inhibitors
Inventor: SCHAETZER JUERGEN
IPC: C07D405/06
Filed: 2000-05-25
Abstract: 4-Acyl-2,3-dihydro-benzofuran or -benzothiophene derivatives (I) are new, where the acyl residue is derived from a cyclic enone or pyrazole compound.  4-Acyl-2,3-dihydro-benzofuran or -benzothiophene derivatives of formula (I) and their salts, stereoisomers, enantiomers and tautomers are new.  R  = H or T;  T  = 1-4C alkyl; Z'  = O, S, SO or SO2;  R1-R4  = H, alkyl, haloalkyl, alkoxy, haloalkoxy, OH, halo, 1-4C hydroxyalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, (3-6C) alkenyloxy-(1-4C) alkyl, (3-6C) alkynyloxy-(1-4C) alkyl, alkenyl, alkylcarbonyloxy-(1-4C) alkyl, (1-4C) alkoxycarbonyloxy-(1-4C) alkyl, (3-6C) haloalkenyloxy-(1-4C) alkyl, cycloalkoxy-(1-4C) alkyl, cycloalkylmethoxymethyl, alkynyl, CHO, alkylcarbonyl, alkoxycarbonyl, (1-4C) alkoxysulfonyloxy-(1-4C) alkyl, (1-4C) alkoxycarbonylalkyl, CN, cyano-(1-4C) alkyl, (1-4C) alkoxycarbonyl-alkenyl, benzyloxyalkyl or CH(OR6)OR7); or R3 + R4 = =O if Z' = O;  R6, R7  = T; or together form 2-4C alkylene;  R5  = halo, CN, NO2, alkyl, alkoxy, alkoxyalkyl, haloalkyl, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, mono- or dialkylaminosulfonyl, alkylsulfonylamino, haloalkoxy, haloalkylthio, haloalkylsulfonyl, SF5 or alkylsulfonyloxy;  Q  = e.g. a group of formulae (i) or (ii);  R8, R66  = OH, halo, alkoxy, (1-18C) alkylcarbonyloxy, alkoxycarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, alkylcarbamoyloxy, dialkylamino, alkylthio, alkylsulfinyl, alkylsulfonyl, (1-4C) alkoxycarbonyl-(1-4C) alkylthio, (1-4C) alkoxycarbonyl-(1-4C) alkylsulfinyl, (1-4C) alkoxycarbonyl-(1-4C) alkylsulfonyl, alkenylthio, alkenylsulfinyl, alkenylsulfonyl, alkylsulfonyloxy, OCH2Ph', OCOPh', OCH2COPh', SPh', SOPh', SO2Ph' or OSO2Ph';  Ph'  = phenyl (optionally substituted by T', OT', COT, COOT, halo, NO2, COOH or CN);  T'  = T or 1-4C haloalkyl;  R9, R10, R13, R14  = H, alkyl, haloalkyl, alkenyl, alkynyl, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylaminosulfonyl, mono- or dialkylamino, OH, alkoxy, 3-6C alkenyloxy, 3-6C alkynyloxy, hydroxyalkyl, (1-4C) alkylsulfonyloxy-alkyl, tosyloxyalyl, halo, CN, NO2 or Ph'';  Ph''  = phenyl (optionally substituted by halo, T', OT', CN, NO2, ST, SOT, SO2T, NT2, COT or SO2NT2);  R11  = H, alkyl, alkoxy, haloalkyl, (1-4C) alkoxy-(1-4C) alkyl, (1-4C) alkylthio-(1-4C) alkyl, (1-4C) alkylcarbonyloxy-(1-4C) alkyl, (1-4C) alkylsulfonyloxy-(1-4C) alkyl, tosyloxy-(1-4C) alkyl, di-(1-3C alkoxyalkyl)-methyl, di-(1-3C alkylthioalkyl)-methyl, (1-3C alkoxyalkyl)-(1-3C alkylthioalkyl)-methyl, 3-5C oxacycloalkyl, 3-5C thiacycloalkyl, 3-4C dioxacycloalkyl, 3-4C dithiacycloalkyl, COOT or Ph'';  R12  = H or T'; or R9 + R10, R13 + R14 or R11 + R12  = 2-6C alkylene;  V'  = 1-4C alkylene, O, S, NR68, SO or SO2;  R68  = T or COT;  R67, R15-R19  = H, alkyl, alkoxycarbonyl, alkenyl, alkynyl, alkylthio, alkylsulfinyl, alkylsulfonyl, SO2NHT, T', NHT, NT2, alkoxy, CN, NO2, halo or Ph;  q  = 1 or 2; and provided that R1-R4 are other than H, alkyl, haloalkyl, alkoxy, haloalkoxy, OH or halo if Q = (i) or (viii); unless specified otherwise alkyl moieties have 1-6C, alkenyl or alkynyl moieties 2-6C and cycloalkyl moieties 3-6C. The full definition is given in the DEFINITION (Full Definition) field. Independent claims are included for: (1) the preparation of (I); and (2) new carboxylic acid intermediates of formula (II).