Pyrimidine derivatives and their use for controlling undesired plant growth
View Patent ↗Compounds of the formula (I) and their agrochemically compatible salts and their use in the field of crop protection are described.
1. A herbicidal compound of formula (I) and/or an agrochemically compatible salt thereof
In which
R 1 is selected from the group consisting of
halogen, hydroxy, cyano, nitro, amino, C(O)OH, C(O)NH 2 ;
(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-haloalkylcarbonyl, (C 1 -C 6 )-alkylcarbonyloxy, (C 1 -C 6 )-haloalkylcarbonyloxy, (C 1 -C 6 )-alkylcarbonyl-(C 1 -C 4 )-alkyl;
(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-haloalkoxycarbonyl, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkoxycarbonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkoxycarbonyl-(C 1 -C 6 )-haloalkyl;
(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkenylcarbonyl, (C 2 -C 6 )-haloalkenylcarbonyl, (C 2 -C 6 )-alkenyloxy, (C 2 -C 6 )-haloalkenyloxy, (C 2 -C 6 )-alkenyloxycarbonyl, (C 2 -C 6 )-haloalkenyloxycarbonyl;
(C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 2 -C 6 )-alkynylcarbonyl, (C 2 -C 6 )-haloalkynylcarbonyl, (C 2 -C 6 )-alkynyloxy, (C 2 -C 6 )-haloalkynyloxy, (C 2 -C 6 )-alkynyloxycarbonyl, (C 2 -C 6 )-haloalkynyloxycarbonyl;
tri(C 1 -C 6 )-alkylsilyl-(C 2 -C 6 )-alkynyl, di(C 1 -C 6 )-alkylsilyl-(C 2 -C 6 )-alkynyl, mono(C 1 -C 6 )-alkylsilyl-(C 2 -C 6 )-alkynyl; phenylsilyl-(C 2 -C 6 )-alkynyl;
(C 6 -C 14 )-aryl, (C 6 -C 14 )-aryloxy, (C 6 -C 14 )-arylcarbonyl and (C 6 -C 14 )-aryloxycarbonyl, which may in each case be substituted on the aryl moiety by halogen, (C 1 -C 6 )-alkyl and/or (C 1 -C 6 )-haloalkyl;
(C 6 -C 14 )-aryl-(C 1 -C 6 )-alkyl, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkoxy, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkylcarbonyl, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkylcarbonyloxy, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkoxycarbonyl, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkoxycarbonyloxy;
mono((C 1 -C 6 )-alkyl)amino, mono((C 1 -C 6 )-haloalkyl)amino, di((C 1 -C 6 )-alkyl)amino, di((C 1 -C 6 )-haloalkyl)amino, ((C 1 -C 6 )-alkyl-(C 1 -C 6 )-haloalkyl)amino, N—((C 1 -C 6 )-alkanoyl)amino, N—((C 1 -C 6 )-haloalkanoyl)amino, aminocarbonyl-(C 1 -C 6 )-alkyl, di(C 1 -C 6 )-alkylaminocarbonyl-(C 1 -C 6 )-alkyl;
mono((C 1 -C 6 )-alkyl)aminocarbonyl, mono((C 1 -C 6 )-haloalkyl)aminocarbonyl, di((C 1 -C 6 )-alkyl)aminocarbonyl, di((C 1 -C 6 )-haloalkyl)aminocarbonyl, ((C 1 -C 6 )-alkyl-(C 1 -C 6 )-haloalkyl)aminocarbonyl, N—((C 1 -C 6 )-alkanoyl)aminocarbonyl, N—((C 1 -C 6 )-haloalkanoyl)aminocarbonyl, mono((C 6 -C 14 )-aryl)aminocarbonyl, di((C 6 -C 14 )-aryl)aminocarbonyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-alkoxy;
(C 3 -C 8 )-cycloalkyl, which may be optionally substituted on the cycloalkyl radical by (C 1 -C 6 )-alkyl and/or halogen; (C 3 -C 8 )-cycloalkoxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-haloalkyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkoxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-haloalkoxy, (C 3 -C 8 )-cycloalkylcarbonyl, (C 3 -C 8 )-cycloalkoxycarbonyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkylcarbonyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-haloalkylcarbonyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkoxycarbonyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-haloalkoxycarbonyl, (C 3 -C 8 )-cycloalkylcarbonyloxy, (C 3 -C 8 )-cycloalkoxycarbonyloxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkylcarbonyloxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-haloalkylcarbonyloxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkoxycarbonyloxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-haloalkoxycarbonyloxy;
(C 3 -C 8 )-cycloalkenyl, (C 3 -C 8 )-cycloalkenyloxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkoxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkoxy, (C 3 -C 8 )-cycloalkenylcarbonyl, (C 3 -C 8 )-cycloalkenyloxycarbonyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkylcarbonyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkylcarbonyl, (C 3 -C 8 )-cyclo alkenyl-(C 1 -C 6 )-alkoxycarbonyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkoxycarbonyl, (C 3 -C 8 )-cycloalkenylcarbonyloxy, (C 3 -C 8 )-cycloalkenyloxycarbonyloxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkylcarbonyloxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkylcarbonyloxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkoxycarbonyloxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkoxycarbonyloxy;
hydroxy-(C 1 -C 6 )-alkyl, hydroxy-(C 1 -C 6 )-alkoxy, cyano-(C 1 -C 6 )-alkoxy, cyano-(C 1 -C 6 )-alkyl;
(C 1 -C 6 )-alkylsulfonyl, (C 1 -C 6 )-alkylthio, (C 1 -C 6 )-alkylsulfinyl, (C 1 -C 6 )-haloalkylsulfonyl, (C 1 -C 6 )-haloalkylthio, (C 1 -C 6 )-haloalkylsulfinyl, (C 1 -C 6 )-alkylsulfonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylsulfonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylsulfonyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkylsulfinyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkylsulfonyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkylthio-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkylsulfinyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkylsulfonyloxy, (C 1 -C 6 )-haloalkylsulfonyloxy, (C 1 -C 6 )-alkylthiocarbonyl, (C 1 -C 6 )-haloalkylthiocarbonyl, (C 1 -C 6 )-alkylthiocarbonyloxy, (C 1 -C 6 )-haloalkylthiocarbonyloxy, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 ) alkylthio-(C 1 -C 6 )-alkylcarbonyloxy, (C 4 -C 14 )-arylsulfonyl, (C 6 -C 14 )-arylthio, (C 6 -C 14 )-arylsulfinyl, (C 3 -C 8 )-cycloalkylthio, (C 3 -C 8 )-alkenylthio, (C 3 -C 8 )-cycloalkenylthio, and (C 3 -C 6 )-alkynylthio;
R 2 is selected from the group consisting of
hydrogen, halogen, hydroxy, cyano, nitro, amino, C(O)OH, C(O)NH 2 ;
(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-haloalkylcarbonyl, (C 1 -C 6 )-alkylcarbonyloxy, (C 1 -C 6 )-haloalkylcarbonyloxy, (C 1 -C 6 )-alkylcarbonyl-(C 1 -C 4 )-alkyl;
(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 1 -C 6 )-alkoxycarbonyl, haloalkoxycarbonyl, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkoxycarbonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkoxycarbonyl-(C 1 -C 6 )-haloalkyl;
(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkenylcarbonyl, (C 2 -C 6 )-haloalkenylcarbonyl, (C 2 -C 6 )-alkenyloxy, (C 2 -C 6 )-haloalkenyloxy, (C 2 -C 6 )-alkenyloxycarbonyl, (C 2 -C 6 )-haloalkenyloxycarbonyl;
(C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 2 -C 6 )-alkynylcarbonyl, (C 2 -C 6 )-haloalkynylcarbonyl, (C 2 -C 6 )-alkynyloxy, (C 2 -C 6 )-haloalkynyloxy, (C 2 -C 6 )-alkynyloxycarbonyl, (C 2 -C 6 )-haloalkynyloxycarbonyl;
tri(C 1 -C 6 )-alkylsilyl-(C 2 -C 6 )-alkynyl, di(C 1 -C 6 )-alkylsilyl-(C 2 -C 6 )-alkynyl, mono(C 1 -C 6 )-alkylsilyl-(C 2 -C 6 )-alkynyl; phenylsilyl-(C 7 -C 6 )-alkynyl;
(C 6 -C 14 )-aryl, (C 6 -C 14 )-aryloxy, (C 6 -C 14 )-arylcarbonyl and (C 6 -C 14 )-aryloxycarbonyl, which may in each case be substituted on the aryl moiety by halogen, (C 1 -C 6 )-alkyl and/or (C 1 -C 6 )-haloalkyl;
(C 6 -C 14 )-aryl-(C 1 -C 6 )-alkyl, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkoxy, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkylcarbonyl, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkylcarbonyloxy, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkoxycarbonyl, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkoxycarbonyloxy;
mono((C 1 -C 6 )-alkyl)amino, mono((C 1 -C 6 )-haloalkyl)amino, di((C 1 -C 6 )-alkyl)amino, di((C 1 -C 6 )-haloalkyl)amino, ((C 1 -C 6 )-alkyl-(C 1 -C 6 )-haloalkyl)amino, N—((C 1 -C 6 )-alkanoyl)amino, N—((C 1 -C 6 )-halo alkanoyl)amino, aminocarbonyl-(C 1 -C 6 )-alkyl, di(C 1 -C 6 )-alkylaminocarbonyl-(C 1 -C 6 )-alkyl;
mono((C 1 -C 6 )-alkyl)aminocarbonyl, mono((C 1 -C 6 )-haloalkyl)aminocarbonyl, di((C 1 -C 6 )-alkyl)aminocarbonyl, di((C 1 -C 6 )-haloalkyl)aminocarbonyl, ((C 1 -C 6 )-alkyl-(C 1 -C 6 )-haloalkyl)aminocarbonyl, N—((C 1 -C 6 )-alkanoyl)aminocarbonyl, N—((C 1 -C 6 )-haloalkanoyl)aminocarbonyl, mono((C 6 -C 14 )-aryl)aminocarbonyl, di((C 6 -C 14 )-aryl)aminocarbonyl,
(C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-alkoxy;
(C 3 -C 8 )-cycloalkyl, which may be optionally substituted on the cycloalkyl radical by (C 1 -C 6 )-alkyl and/or halogen; (C 3 -C 8 )-cycloalkoxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-haloalkyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkoxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-haloalkoxy, (C 3 -C 8 )-cycloalkylcarbonyl, (C 3 -C 8 )-cycloalkoxycarbonyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkylcarbonyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-haloalkylcarbonyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkoxycarbonyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-haloalkoxycarbonyl, (C 3 -C 8 )-cycloalkylcarbonyloxy, (C 3 -C 8 )-cycloalkoxycarbonyloxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkylcarbonyloxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-haloalkylcarbonyloxy, (C 1 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkoxycarbonyloxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-haloalkoxycarbonyloxy;
(C 3 -C 8 )-cycloalkenyl, (C 3 -C 8 )-cycloalkenyloxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkoxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkoxy, (C 3 -C 8 )-cycloalkenylcarbonyl, (C 3 -C 8 )-cycloalkenyloxycarbonyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkylcarbonyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkylcarbonyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkoxycarbonyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkoxycarbonyl, (C 3 -C 8 )-cycloalkenylcarbonyloxy, (C 3 -C 8 )-cycloalkenyloxycarbonyloxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkylcarbonyloxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkylcarbonyloxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkoxycarbonyloxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkoxycarbonyloxy;
hydroxy-(C 1 -C 6 )-alkyl, hydroxy-(C 1 -C 6 )-alkoxy, cyano-(C 1 -C 6 )-alkoxy, cyano-(C 1 -C 6 )-alkyl;
(C 1 -C 6 )-alkylsulfonyl, (C 1 -C 6 )-alkylthio, (C 1 -C 6 )-alkylsulfinyl, (C 1 -C 6 )-haloalkylsulfonyl, (C 1 -C 6 )-haloalkylthio, (C 1 -C 6 )-haloalkylsulfinyl, (C 1 -C 6 )-alkylsulfonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkythio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylsulfonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylsulfonyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkylsulfinyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkylsulfonyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkylthio-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkylsulfinyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkylsulfonyloxy, (C 1 -C 6 )-haloalkylsulfonyloxy, (C 1 -C 6 )-alkylthiocarbonyl, (C 1 -C 6 )-haloalkylthiocarbonyl, (C 1 -C 6 )-alkylthiocarbonyloxy, (C 1 -C 6 )-haloalkylthiocarbonyloxy, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkylcarbonyloxy, (C 4 -C 14 )-arylsulfonyl, (C 6 -C 14 )-arylthio, (C 6 -C 14 )-arylsulfinyl, (C 3 -C 8 )-cycloalkylthio, (C 3 -C 8 )-alkenylthio, (C 3 -C 8 )-cycloalkenylthio, and (C 1 -C 6 )-alkynylthio;
Or the radicals R 1 and R 2 together may form a (C 2 -C 6 )-alkylene group, which may comprise one or more oxygen and/or sulfur atoms, where the (C 2 -C 6 )-alkylene group may be mono- or polysubstituted by halogen and the respective halogen substituents may be identical or different; and
R 3 is selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-haloalkyl;
R 4 and R 5 in each case independently of one another are selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, hydroxy, (C 1 -C 6 )-alkoxy and (C 1 -C 6 )-haloalkoxy; or the radicals R 4 and R 5 , together with the carbon atom to which they are bonded, may form a three- to seven-membered ring;
R 6 and R 7 in each case independently of one another are selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 6 -C 14 )-aryl, (C 6 -C 14 )-aryloxy, (C 6 -C 14 )-arylcarbonyl and (C 6 -C 14 )-aryloxycarbonyl; or the radicals R 6 and R 7 together may form a (C 2 -C 7 )-alkylene group, which may comprise one or more oxygen and/or sulfur atoms, where the (C 2 -C 7 )-alkylene group may be mono- or polysubstituted by halogen and the respective halogen substituents may be identical or different,
R 8 , R 9 , R 10 and R 11 , independently of one another, are in each case selected from the group consisting of hydrogen, halogen, cyano, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-alkyloxycarbonyl, (C 1 -C 6 )-alkylaminocarbonyl, (C 1 -C 6 )-dialkylaminocarbonyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 2 -C 6 )-alkynylcarbonyl, (C 2 -C 6 )-haloalkynylcarbonyl, (C 2 -C 6 )-alkynyloxy, (C 2 -C 6 )-haloalkynyloxy, (C 2 -C 6 )-alkynyloxycarbonyl and (C 2 -C 6 )-haloalkynyloxycarbonyl and nitro;
X is selected from the group consisting of a chemical bond, CH 2 , O, S, carbonyl, NH, CR 12 R 13 , and NR 14 ;
R 12 and R 13 in each case independently of one another are selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-haloalkyl;
R 14 is selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl, and (C 1 -C 6 )-haloalkyl; and
wherein the stereochemical configuration on the carbon atom indicated by (*) is (R).
2. A herbicidal compound of the formula (I) as claimed in claim 1 , wherein the radical X is selected from the group consisting of CH 2 , O and a chemical bond.
3. A herbicidal compound of the formula (I) as claimed in claim 1 , wherein the radical R 1 is selected from the group consisting of halogen, cyano, C(═O)NH 2 , NO 2 , (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 6 )-cyclopropyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-thioalkyl, (C 1 -C 6 )-alkylthio, (C 2 -C 6 )-alkynyl, mono(C 1 -C 6 )-alkylamino, di(C 1 -C 6 )-alkylamino and tri(C 1 -C 6 )-alkylsilyl-(C 2 -C 6 )-alkynyl.
4. A herbicidal compound of the formula (I) as claimed in claim 1 , wherein the radical R 2 is selected from the group consisting of hydrogen, halogen, (C 1 -C 6 )-alkylphenyl; (C 6 -C 14 )-aryl, which may be substituted on the aryl radical by (C 1 -C 6 )-alkyl, (C 6 -C 14 )-haloalkyl and/or halogen; C 6 -aryl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl; (C 3 -C 6 )-cycloalkyl, which may be substituted on the cycloalkyl radical by (C 1 -C 6 )-alkyl, (C 6 -C 14 )-haloaryl and/or halogen; 1-(C 1 -C 6 )-alkylcyclopropyl, 1-((C 1 -C 6 )-alkyl-C 6 -aryl)cyclopropyl, 1-(monohalophenyl)cyclopropyl, 1-(dihalophenyl)cyclopropyl, mono (C 1 -C 6 )-alkylamino, di(C 1 -C 6 )-alkylamino, (C 1 -C 6 )-thioalkyl, (C 1 -C 6 )-alkylthio, (C 1 -C 6 )-alkoxy and amino.
5. A herbicidal compound of the formula (I) as claimed in claim 1 , wherein the radicals R 1 and R 2 , together with the carbon atoms to which they are bonded, form a five- or six-membered ring, which may be interrupted by one or two heteroatoms selected from the group consisting of oxygen and sulfur.
6. A herbicidal compound of the formula (I) as claimed in claim 1 , wherein the radical R 3 is hydrogen or (C 1 -C 6 )-alkyl.
7. A herbicidal compound of the formula (I) as claimed in claim 1 , wherein the radicals R 4 and R 5 , in each case independently of one another, are selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl, hydroxy, cyclopropyl and (C 1 -C 6 )-alkoxy.
8. A herbicidal compound of the formula (I) as claimed in claim 1 , wherein the radicals R 4 and R 5 , together with the carbon atom to which they are bonded, form a three- to seven-membered ring.
9. A herbicidal compound of the formula (I) as claimed in claim 1 , wherein the radicals R 6 and R 7 , independently of one another, are selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl and (C 6 -C 14 )-aryl.
10. A herbicidal compound of the formula (I) as claimed in claim 1 , wherein the radical R 8 is selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl and halogen.
11. A herbicidal compound of the formula (I) as claimed in claim 1 , wherein the radical R 9 is selected from the group consisting of hydrogen and (C 1 -C 6 )-alkyl.
12. A herbicidal compound of the formula (I) as claimed in claim 1 , wherein the radical R 10 is selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl, di(C 1 -C 6 )-alkylamino, halogen, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 1 -C 6 )-alkyl-(C 2 -C 6 )-alkynyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl-(C 2 -C 6 )-alkynyl, cyano, (C 1 -C 6 )-alkoxycarbonyl and aminocarbonyl.
13. A herbicidal compound of the formula (I) as claimed in claim 1 , wherein the radical R 11 is selected from the group consisting of hydrogen and (C 1 -C 6 )-alkyl.
14. A process for the preparation of a herbicidal compound of formula (I)
and/or salt thereof according to claim 1 , which comprises (1) reacting a compound of formula (II)
wherein Z 1 is an exchangeable radical or a leaving group, with an amine of formula (III) or an acid addition salt thereof
(2) reacting a derivative of formula (I) where R 1 , R 2 or R 10 =halogen, with acetylene or trimethylsilyl-protected acetylene with transition metal catalysis, in a protic or aprotic solvent and the addition of a base at a temperature from 20 to 150° C. to give a compound of formula (I) where R 1 , R 2 or R 10 =alkynyl;
(3) saponifying a derivative of formula (I) where R 1 ═CN with acidic or basic catalysis and converting carboxylic acids obtained into acid chlorides and, converting into amides;
(4) converting a derivative of formula (I) where R 2 =halogen in a protic or aprotic solvent and addition of a base at a temperature from 100 to 200° C. through reaction with an alcoholate or amine to give a compound of formula (I) where R 2 =alkoxyalkyl or aminoalkyl or diaminoalkyl.
15. A herbicidal or plant growth regulating composition, which comprises one or more herbicidal compounds of the formula (I) or salts thereof as claimed in claim 1 .
16. A method for controlling harmful plants or for regulating the growth of plants, which comprises applying an effective amount of one or more herbicidal compounds of the formula (I) or salts thereof as claimed in claim 1 to plants, plant parts, plant seeds and/or to an area under cultivation.
17. A herbicidal compound of the formula (I) as claimed in claim 2 , wherein the radical R 1 is selected from the group consisting of halogen, cyano, C(═O)NH 2 , NO 2 , (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 6 )-cyclopropyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-thioalkyl, (C 1 -C 6 )-alkylthio, (C 2 -C 6 )-alkynyl, mono(C 1 -C 6 )-alkylamino, di(C 1 -C 6 )-alkylamino and tri(C 1 -C 6 )-alkylsilyl-(C 2 -C 6 )-alkynyl.
18. A herbicidal compound of the formula (I) as claimed in claim 2 , wherein the radical R 2 is selected from the group consisting of hydrogen, halogen, (C 1 -C 6 )-alkylphenyl; (C 6 -C 14 )-aryl, which may be substituted on the aryl radical by (C 1 -C 6 )-alkyl, (C 6 -C 14 )-haloalkyl and/or halogen; C 6- aryl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl; (C 3 -C 6 )-cycloalkyl, which may be substituted on the cycloalkyl radical by (C 1 -C 6 )-alkyl, (C 6 -C 14 )-haloaryl and/or halogen; 1-(C 1 -C 6 )-alkylcyclopropyl, 1-((C 1 -C 6 )-alkyl-C 6 -aryl)cyclopropyl, 1-(monohalophenyl)cyclopropyl, 1-(dihalophenyl)cyclopropyl, mono (C 1 -C 6 )-alkylamino, di(C 1 -C 6 )-alkylamino, (C 1 -C 6 )-thioalkyl, (C 1 -C 6 )-alkylthio, (C 1 -C 6 )-alkoxy and amino.
19. A herbicidal compound of the formula (I) as claimed in claim 2 , wherein the radicals R 1 and R 2 , together with the carbon atoms to which they are bonded, form a five- or six-membered ring, which may be interrupted by one or two heteroatoms selected from the group consisting of oxygen and sulfur.
20. A herbicidal compound of the formula (I) as claimed in claim 2 , wherein the radical R 3 is hydrogen or (C 1 -C 6 )-alkyl.
21. A herbicidal compound according to claim 1 , selected from the group consisting of