3-amino-1,2,4-triazine derivatives and their use for controlling undesired plant growth

A compound of formula (I)

• and/or an agrochemically acceptable salt thereof in which
• R1 represents hydrogen, amino, hydrazino, hydroxyamino, ((C1-C6)-alkyl)-amino, ((C3-C6)-cycloalkyl)-amino, di-((C1-C6)-alkyl)-amino, (C1-C6)-alkylcarbonylamino, bis-((C1-C6)-alkyl)-carbonylamino;
• R2 is selected from the group consisting of hydrogen, halogen, hydroxy, nitro, amino, cyano, C(O)OH, C(O)NH2;
• (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)-alkoxy, (C1-C6)-haloalkoxy, (C1-C6)-alkoxycarbonyl, (C1-C6)-haloalkoxycarbonyl, (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;
• tri-(C1-C6)-alkylsilyl-(C2-C6)-alkynyl, di-(C1-C6)-alkylsilyl-(C2-C6)-alkynyl, (C1-C6)-alkylsilyl-(C2-C6)-alkynyl;
• phenylsilyl-(C2-C6)-alkynyl;
• (C6-C14)-aryl, (C6-C14)-aryloxy, (C6-C14)-arylcarbonyl and (C6-C14)-aryloxycarbonyl, each of which may be substituted in the aryl moiety by halogen, (C1-C6)-alkyl and/or (C1-C6)-haloalkyl;
• (C6-C14)-aryl-(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;
• aminocarbonyl-(C1-C6)-alkyl, di-(C1-C6)-alkylaminocarbonyl-(C1-C6)-alkyl;
• N—((C1-C6)-haloalkanoyl)aminocarbonyl, ((C6-C14)-aryl)aminocarbonyl, di-((C6-C14)-aryl)aminocarbonyl, ((C1-C6)-alkyl)aminocarbonyl, di-((C1-C6)-alkyl)aminocarbonyl, N—((C1-C6)-alkylsulfonyl)aminocarbonyl, N—((C1-C6)-haloalkylsulfonyl)aminocarbonyl, N—((C6-C14)-arylsulfonyl)aminocarbonyl;
• (C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkoxy, (C1-C6)-alkoxycarbonyl-(C1-C6)-alkoxy;
• (C3-C8)-cycloalkyl which may optionally be substituted in the cycloalkyl radical by (C1-C6)-alkyl and/or halogen;
• (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;
• hydroxy-(C1-C6)-alkyl, hydroxy-(C1-C6)-alkoxy, cyano-(C1-C6)-alkoxy, cyano-(C1-C6)-alkyl;
• and (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, (C1-C6)-alkylthiocarbonyl, (C1-C6)-haloalkylthiocarbonyl, (C1-C6)-alkylthiocarbonyloxy, (C1-C6)-haloalkylthiocarbonyloxy, (C1-C6)-alkylthio-(C1-C6)-alkyl, (C1-C6)-alkylthio-(C1-C6)-alkoxy, (C1-C6)-alkylthio-(C1-C6)-alkylcarbonyl, (C1-C6)-alkylthio-(C1-C6)-alkylcarbonyloxy;
• (C4-C14)-arylsulfonyl, (C6-C14)-arylthio, (C6-C14)-arylsulfinyl, (C3-C8)-cycloalkylthio, (C3-C8)-alkenylthio, (C3-C8)-cycloalkenylthio and (C3-C6)-alkynylthio;
• or
• R1 may be attached to R2 via a bond, resulting in a 5- to 7-membered partially hydrogenated carbocycle or heterocycle having at least one heteroatom selected from the group consisting of N, O, S and P, which carbocycle or heterocycle is optionally substituted by one or more substituents selected from the group consisting of hydroxy, ═O, ═N—O—H, ═N—O—(C1-C6)-alkyl, ═N—O-benzyl, ═N—O-phenyl, phenyl, phenyl substituted by one or more identical or different halogen atoms, (C1-C6)-alkyl, (C3-C6)-cycloalkyl and (C1-C6)-haloalkyl;
• R3 is selected from the group consisting of hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C6)-alkoxycarbonyl and aminocarbonyl;
• R4 and R5 are each independently of one another selected from the group consisting of hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, hydroxy, (C1-C6)-alkoxy and (C1-C6)-haloalkoxy;
• or
• R4 and R5 together with the carbon atom to which they are attached form a saturated three- to seven-membered ring which may contain one or more heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen;
• R6 and R7 are each independently of one another selected from the group consisting of hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C6-C14)-aryl, (C6-C14)-aryloxy, (C6-C14)-arylcarbonyl and (C6-C14)-aryloxycarbonyl;
• or the R6 and R7 radicals together form a (C1-C7)-alkylene group which may contain one or more oxygen and/or sulfur atoms, where the (C1-C7)-alkylene group may be mono- or polysubstituted by halogen and the respective halogen substituents may be identical or different;
• n is 0, 1 or 2;
• R8, R9, R10 and R11 are each independently of one another selected from the group consisting of hydrogen, halogen, cyano, C(O)OH, C(O)NH2, (C1-C6)-alkyl, (C1-C6)-alkylcarbonyl, (C1-C6)-alkyloxycarbonyl, (C1-C6)-alkylaminocarbonyl, (C1-C6)-dialkylaminocarbonyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C2-C6)-alkynylcarbonyl, (C2-C6)-haloalkynylcarbonyl, (C2-C6)-alkynyloxy, (C2-C6)-haloalkynyloxy, (C2-C6)-alkynyloxycarbonyl, (C2-C6)-haloalkynyloxycarbonyl and nitro, where the R9 and R10 radicals may be attached to one another via an —O—CH2—O— group forming a ring;
• X represents a bond, CH2, O, S, carbonyl, NH, CR12R13, NR14, CH2O or CH2S, where in the two last-mentioned groups the carbon atom is attached to the aromatic moiety and the heteroatom O or S is attached to the partially hydrogenated moiety of the amine;
• R12 and R13 are each independently of one another selected from the group consisting of hydrogen, (C1-C6)-alkyl and (C1-C6)-haloalkyl;
• and
• R14 is selected from the group consisting of hydrogen, (C1-C6)-alkyl and (C1-C6)-haloalkyl.