Chiral3-(benzylsulfinyl)-5,5-dimethyl-4,5-dihydroisoxazole derivatives and 5,5-dimethyl-3-[(1h-pyrazol-4-ylmethyl)sulfinyl]-4,5-dihyddroisoxazole derivatives, method for the production thereof, and use of same as herbicides and plant growth regulators

An optically active compound of the formula (I) in the form of its (S) stereoisomer and/or an agrochemically acceptable salt and/or an agrochemically acceptable quaternized nitrogen derivative thereof

• wherein
• Y is
• and
• the individual substituents R1 to R5 are each independently of one another selected from the group consisting of
• hydrogen, halogen, hydroxyl, cyano, nitro, amino, C(O)OH, formyl,
• (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkylcarbonyl, (C1-C6)-haloalkylcarbonyl, (C1-C6)-alkylcarbonyloxy, (C1-C6)-haloalkylcarbonyloxy, (C1-C6)-alkylcarbonyl-(C1-C4)-alkyl, (C1-C6)-haloalkylcarbonyl-(C1-C4)-alkyl, (C1-C6)-alkylcarbonyl-(C1-C4)-haloalkyl, (C1-C6)-haloalkylcarbonyl-(C1-C4)-haloalkyl,
• (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C1-C6)-alkoxycarbonyl, (C1-C6)-halo-alkoxycarbonyl, (C1-C6)-alkoxycarbonyl-(C1-C6)-alkyl, (C1-C6)-haloalkoxycarbonyl-(C1-C6)-alkyl, (C1-C6)-alkoxycarbonyl-(C1-C6)-haloalkyl, (C1-C6)-haloalkoxycarbonyl-(C1-C6)-haloalkyl,
• (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkenylcarbonyl, (C2-C6)-haloalkenylcarbonyl, (C2-C6)-alkenyloxy, (C2-C6)-haloalkenyloxy, (C2-C6)-alkenyloxycarbonyl, (C2-C6)-haloalkenyloxycarbonyl,
• (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C2-C6)-alkynylcarbonyl, (C2-C6)-haloalkynylcarbonyl, (C2-C6)-alkynyloxy, (C2-C6)-haloalkynyloxy, (C2-C6)-alkynyloxycarbonyl, (C2-C6)-haloalkynyloxycarbonyl,
• (C1-C6)-alkylthiocarbonyl, (C1-C6)-haloalkylthiocarbonyl, (C1-C6)-alkylthiocarbonyloxy, (C1-C6)-haloalkylthiocarbonyloxy,
• (C1-C6)-alkylthio-(C1-C6)-alkoxy, (C1-C6)-alkylthio-(C1-C6)-alkylcarbonyl, (C1-C6)-alkylthio-(C1-C6)-alkylcarbonyloxy,
• (C6-C14)-aryl, (C6-C14)-aryloxy, (C6-C14)-arylcarbonyl, (C6-C14)-aryloxycarbonyl,
• (C6-C14)-aryl-(C1-C6)-alkyl,(C6-C14)-aryloxy-(C1-C6)-alkyl, (C6-C14)-aryl-(C1-C6)-alkoxy, (C6-C14)-aryl-(C1-C6)-alkylcarbonyl, (C6-C14)-aryl-(C1-C6)-alkylcarbonyloxy, (C6-C14)-aryl-(C1-C6)-alkoxycarbonyl, (C6-C14)-aryl-(C1-C6)-alkoxycarbonyloxy,
• (C1-C6)-alkylsulfonyl, (C1-C6)-alkylthio, (C1-C6)-alkylsulfinyl, (C1-C6)-haloalkylsulfonyl, (C1-C6)-haloalkylthio, (C1-C6)-haloalkylsulfinyl, (C1-C6)-alkylsulfonyl-(C1-C6)-alkyl, (C1-C6)-alkylthio-(C1-C6)-alkyl, (C1-C6)-alkylsulfinyl-(C1-C6)-alkyl, (C1-C6)-haloalkylsulfonyl-(C1-C6)-alkyl, (C1-C6)-haloalkylthio-(C1-C6)-alkyl, (C1-C6)-haloalkylsulfinyl-(C1-C6)-alkyl, (C1-C6)-alkylsulfonyl-(C1-C6)-haloalkyl, (C1-C6)-alkylthio-(C1-C6)-haloalkyl, (C1-C6)-alkylsulfinyl-(C1-C6)-haloalkyl, (C1-C6)-haloalkylsulfonyl-(C1-C6)-haloalkyl, (C1-C6)-haloalkylthio-(C1-C6)-haloalkyl, (C1-C6)-haloalkylsulfinyl-(C1-C6)-haloalkyl, (C1-C6)-alkylsulfonyloxy, (C1-C6)-haloalkylsulfonyloxy,
• (C4-C14)-arylsulfonyl, (C6-C14)-arylthio, (C6-C14)-arylsulfinyl,
• mono-((C1-C6)-alkyl)-amino, mono-((C1-C6)-haloalkyl)-amino, di-((C1-C6)-alkyl)-amino, di-((C1-C6)-haloalkyl)-amino, ((C1-C6)-alkyl-(C1-C6)-haloalkyl)-amino, N-((C1-C6)-alkanoyl)-amino, N-((C1-C6)-haloalkanoyl)-amino, aminocarbonyl-(C1-C6)-alkyl, mono-(C1-C6)-alkylaminocarbonyl-(C1-C6)-alkyl, mono-((C1-C6)-alkyl)-aminocarbonyl, di-(C1-C6)-alkylaminocarbonyl-(C1-C6)-alkyl,
• (C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkoxy, (C1-C6)-alkoxycarbonyl-(C1-C6)-alkoxy,
• (C3-C8)-cycloalkyl, (C3-C8)-cycloalkoxy, (C3-C8)-cycloalkyl-(C1-C6)-alkyl, (C3-C8)-cycloalkyl-(C1-C6)-haloalkyl, (C3-C8)-cycloalkyl-(C1-C6)-alkoxy, (C3-C8)-cycloalkyl-(C1-C6)-haloalkoxy, (C3-C8)-cycloalkylcarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C3-C8)-cycloalkyl-(C1-C6)-alkylcarbonyl, (C3-C8)-cycloalkyl-(C1-C6)-haloalkylcarbonyl, (C3-C8)-cycloalkyl-(C1-C6)-alkoxycarbonyl, (C3-C8)-cycloalkyl-(C1-C6)-haloalkoxycarbonyl, (C3-C8)-cycloalkylcarbonyloxy, (C3-C8)-cycloalkoxycarbonyloxy, (C3-C8)-cycloalkyl-(C1-C6)-alkylcarbonyloxy, (C3-C8)-cycloalkyl-(C1-C6)-haloalkylcarbonyloxy, (C3-C8)-cycloalkyl-(C1-C6)-alkoxycarbonyloxy, (C3-C8)-cycloalkyl-(C1-C6)-haloalkoxycarbonyloxy,
• (C3-C8)-cycloalkenyl, (C3-C8)-cycloalkenyloxy, (C3-C8)-cycloalkenyl-(C1-C6)-alkyl, (C3-C8)-cycloalkenyl-(C1-C6)-haloalkyl, (C3-C8)-cycloalkenyl-(C1-C6)-alkoxy, (C3-C8)-cycloalkenyl-(C1-C6)-haloalkoxy, (C3-C8)-cycloalkenylcarbonyl, (C3-C8)-cycloalkenyloxycarbonyl, (C3-C8)-cycloalkenyl-(C1-C6)-alkylcarbonyl, (C3-C8)-cycloalkenyl-(C1-C6)-haloalkylcarbonyl, (C3-C8)-cycloalkenyl-(C1-C6)-alkoxycarbonyl, (C3-C8)-cycloalkenyl-(C1-C6)-haloalkoxycarbonyl, (C3-C8)-cycloalkenylcarbonyloxy, (C3-C8)-cycloalkenyloxycarbonyloxy, (C3-C8)-cycloalkenyl-(C1-C6)-alkylcarbonyloxy, (C3-C8)-cycloalkenyl-(C1-C6)-haloalkylcarbonyloxy, (C3-C8)-cycloalkenyl-(C1-C6)-alkoxycarbonyloxy, (C3-C8)-cycloalkenyl-(C1-C6)-haloalkoxycarbonyloxy,
• (C3-C8)-cycloalkylthio, (C3-C8)-alkenylthio, (C3-C8)-cycloalkenylthio, (C3-C6)-alkynylthio,
• hydroxy-(C1-C6)-alkyl, hydroxy-(C1-C6)-alkoxy, cyano-(C1-C6)-alkoxy, cyano-(C1-C6)-alkyl,
• 3-oxetanyloxy,
• pyrimidinyl-2-yl and 4,6-dimethoxypyrimidinyl-2-yl,
• C(O)NR9R10 where R9 and R10 independently of one another are hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, or where R9 and R10 together form a (C1-C6)-alkylene group which may contain one oxygen or sulfur atom or one or two amino or (C1-C6)-alkylamino groups,
• where the radicals mentioned may, if appropriate, be attached cyclically to one another, provided they are ortho to one another
• and/or
• two substituents ortho to one another together form a (C1-C6)-alkylene group which may contain one or more oxygen and/or sulfur atoms, where the (C1-C6)-alkylene group may be mono-or polysubstituted by halogen and the halogen substituents in question may be identical or different;
• and
• where the radicals cycloalkyl and aryl may be mono-or polysubstituted independently of one another.