Patent DE-102004023605-A1 (DE)
Title: New (pyrazol-4-yl)-(2,3-dihydro-benzofuran-4-yl or -benzothiophen-4-yl)-methanone derivatives, useful as pre- or post-emergence, total or selective herbicides or plant growth inhibitors
Inventor: BEAUDEGNIES RENAUD
IPC: A01N43/56
Filed: 2004-05-13
Abstract: (5-Substituted 1H-pyrazol-4-yl)-(2,3-dihydro-benzofuran-4-yl or -benzothiophen-4-yl)-methanone derivatives (I) are new. Pyrazole derivatives of formula (I) and their salts, stereoisomers and tautomers are new. [Image] Z : O, S, SO or SO2; R1 - R3(i) H, halo, alkoxy, haloalkoxy, OH, CN, NO2, CHO, COOH, alkoxycarbonyl, ST, SOT or SO2T; (ii) alkyl, alkenyl or alkynyl (all optionally substituted (os) by one or more of halo, OH, CN, NO2, alkoxy, 3-6C alkenyloxy, alkynyloxy, alkoxyalkoxy, haloalkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl or cycloalkoxy (optionally interrupted in the ring by 1 or 2 O and os by alkyl, 1-3C alkoxy or (1-3C) alkoxy-(1-3C) alkoxy)); (iii) phenoxy or benzyloxy (both os by one or more of halo, CN, NO2, alkyl, haloalkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or alkoxyalkyl); or (iv) -CH(OR7)OR8; T : 1-4C alkyl; X : (i) alkyl (os by one or more of CHO, COOH, OH, CN, NO2, alkoxy, 3-6C alkenyloxy, 3-6C alkynyloxy, alkoxyalkoxy, cycloalkylalkoxy, (1-3C) alkoxy-(1-3C) alkoxy-(1-3C) alkoxy, haloalkoxy, 3-6C haloalkenyloxy, 3-6C haloalkynyloxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkoxycarbonyl, alkylcarbonyl, haloalkoxycarbonyl, haloalkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkylsulfonyloxy, cyanoalkoxy, cyanoalkylthio, cyanoalkylsulfinyl, cyanoalkylsulfonyl, alkylthioalkoxy, alkylsulfinylalkoxy, alkylsulfonylalkoxy, alkoxycarbonylalkoxy, mono- or dialkylamino, alkylcarbamoyl, mono- or dialkylaminosulfonyl, alkylsulfonylamino, -C(R11)=NOR12, oxiranyl or cycloalkoxy (where cycloalkyl rings are optionally partially unsaturated, optionally interrupted by 1-4 O, S or N heteroatoms and os by one or more of alkyl, 1-3C alkoxy or (1-3C) alkoxy-(1-3C) alkoxy)); (ii) -CH(OR9)OR10 or -C(R19)=NOR20; or (iii) phenoxy or benzyloxy (both os as in R1); R7 - R10T; or R7 + R8 or R9 + R10 = 2-4C alkylene; R11, R19H or T (os by halo); R12, R20H, alkyl, 3-6C alkenyl, 3-6C alkynyl, 1-4C haloalkyl or 3-6C haloalkenyl; R4halo, CN, NH2, NO2, T (os by OH, OT or halo), OT (os by halo), alkenyl, alkynyl, COT, COOT, ST (os by halo), SOT (os by halo), SO2T (os by halo), SO2NHT, SO2NT2, NHSO2T, SF5, P(O)R13R14 or OSO2T; R13, R14H, OH or T; R5OH, halo, alkoxy, (1-8C) alkylcarbonyloxy, alkoxycarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, (3-6C) cycloalkylcarbonyloxy, alkylcarbamoyloxy, dialkylamino, alkylthio, alkylsulfinyl, alkylsulfonyl, (1-4C) alkoxy-(1-4C) alkylthio, (1-4C) alkoxy-(1-4C) alkylsulfinyl, (1-4C) alkoxy-(1-4C) alkylsulfonyl, alkenylthio, alkenylsulfinyl, alkenylsulfonyl, alkylsulfonyloxy, OCH2Ph', OCOPh', OCH2COPh', SPh', SOPh', SO2Ph' or OSO2Ph'; Ph' : phenyl (os by T (os by halo), OT (os by halo), COT, COOT, halo, NO2, COOH or CN); R6(i) H or COOT; (ii) alkyl, alkenyl, alkynyl or cycloalkyl (all os by one or more of halo, NO2, alkoxy or CN); or (iii) phenyl or benzyl (both os by one or more of alkyl, haloalkyl, alkoxy, haloalkoxy, alkylcarbonyl, alkoxycarbonyl, NH2, NHT, NT2, alkylthio, alkylsulfinyl, alkylsulfonyl, OSO2T (os by halo), 1-4C haloalkylthio, 1-4C haloalkylsulfinyl, 1-4C haloalkylsulfonyl, SO2NHT, SO2NT2, halo, COOH, NO2 or CN); unless specified otherwise alkyl moieties have 1-6C, alkenyl or alkynyl moieties 2-6C and cycloalkyl moieties 3-7C. An independent claim is included for new benzofuran or benzothiophene derivative intermediates of formula (IIa). R18NH2, CHO, 1-6C hydroxyalkyl or P(O)R13R14. ACTIVITY : Herbicide; plant growth regulator. In pre-emergence tests, (5-hydroxy-1-methyl-1H-pyrazol-4-yl)-(7-methanesulfonyl-2-methoxymethyl-2,3-dihydro-benzofuran-4-yl)-methanone (Ia) at an application rate of 250 g/ha had 100% herbicidal effectiveness against Panicum, Digitaria, Amaranthus and Chenopodium. MECHANISM OF ACTION : None given in the source material.