2-(HETERO)ARYLPYRIDAZINONES AND THEIR USE AS HERBICIDES

摘要

2-(Hetero)arylpyradazinones of the general formula (I) are described as herbicides.;;In this formula (I), R1, R2, R3, R4 and R5 are each radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen. X1, X2 and X3 represent nitrogen or an optionally substituted carbon atom.

主权项

1. A 2-(hetero)arylpyridazinone of formula (I) or a salt thereof in which R1 represents hydrogen, halogen, cyano (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C4-C6)-cycloalkenyl, (C2-C6)-alkynyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy, (C1-C6)-alkoxy-(C1-C3)-alkyl, (C1-C6)-alkoxy-(C2-C6)-alkoxy, (C1-C6)-alkoxy-(C2-C6)-alkoxy-(C1-C3)-alkyl, (C3-C6)-cycloalkyl-(C1-C3)-alkyl, amino, (C1-C6)-alkylamino, di-(C1-C6)-alkylamino, (C1-C3)-alkyl-(O)C-amino-(C1-C4)-alkyl, (C1-C6)-alkyl-(O)nS, (C1-C6)-alkyl-(O)nS—(C1-C3)-alkyl, halo-(C1-C6)-alkyl-(O)nS or halo-(C1-C6)-alkyl-(O)nS—(C1-C3)-alkyl; R2 represents hydrogen, hydroxy, halogen, nitro, amino, cyano, (C1-C6)-alkyl, (C1-C3)-alkoxy, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C3)-alkyl, (C3-C6)-cycloalkyl-(C1-C3)-alkyl, (C1-C6)-alkyl-(O)nS, (C1-C6)-alkyl-(O)nS—(C1-C3)-alkyl, halo-(C1-C6)-alkyl-(O)nS, halo-(C1-C6)-alkyl-(O)nS—(C1-C3)-alkyl, (C1-C3)-alkylamino or di-(C1-C3)-alkylamino; R3 represents hydrogen, (C1-C6)-alkyl-(O)C, aryl-(O)C, (C1-C6)-alkoxy-(O)C, (C1-C6)-alkyl-(O)nS, (C1-C6)-alkyl-(O)nS(O)C or aryl-(O)nS, where the aryl groups are in each case substituted by s radicals R9; R4 represents hydroxy, halogen, cyano, nitro, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C3-C6)-cycloalkyl-(C1-C3)-alkyl, (C1-C6)-alkoxy-(C1-C3)-alkyl, (C1-C6)-alkoxy-(C2-C6)-alkoxy, (C1-C6)-alkoxy-(C2-C6)-alkoxy-(C1-C3)-alkyl, halo-(C1-C6)-alkoxy, halo-(C1-C6)-alkoxy-(C1-C3)-alkyl, (C1-C6)-alkyl-(O)nS, halo-(C1-C6)-alkyl-(O)nS, aryl, aryl-(O)nS, heterocyclyl, heterocyclyl-(O)nS, aryloxy, aryl-(C2-C6)-alkyl, aryl-(C1-C6)-alkoxy, heterocyclyloxy, heterocyclyl-(C1-C3)-alkoxy-(C1-C3)-alkyl, HO(O)C, HO(O)C—(C1-C3)-alkoxy, (C1-C3)-alkoxy-(O)C, (C1-C3)-alkoxy-(O)C—(C1-C3)-alkoxy, (C1-C3)-alkylamino, di-(C1-C3)-alkylamino, (C1-C3)-alkylamino-(O)nS, (C1-C3)-alkylamino-(O)nS—(C1-C3)-alkyl, di-(C1-C3)-alkylamino-(O)nS, di-(C1-C3)-alkylamino-(O)nS—(C1-C3)-alkyl, (C1-C3)-alkylamino-(O)C, (C1-C3)-alkylamino-(O)C—(C1-C3)-alkyl, di-(C1-C3)-alkylamino-(O)C, di-(C1-C3)-alkylamino-(O)C—(C1-C3)-alkyl, (C1-C3)-alkyl-(O)C-amino, (C1-C3)-alkyl-(O)nS-amino, (C1-C3)-alkyl-(O)nS—(C1-C3)-alkylamino or (C1-C3)-alkyl-(O)nS-amino-(C1-C3)-alkyl, where the heterocyclyl groups and aryl groups are substituted by s radicals from the group consisting of (C1-C3)-alkyl, halo-(C1-C3)-alkyl, (C1-C3)-alkoxy, halo-(C1-C3)-alkoxy, phenyl, cyano, nitro and halogen; A represents a direct bond or (C1-C4)-alkylene, where the methylene groups in (C1-C4)-alkylene independently of one another may carry n radicals from the group consisting of halogen, (C1-C4)-alkyl, halo-(C1-C4)-alkyl, (C1-C4)-alkoxy, halo-(C1-C4)-alkoxy or (C1-C4)-alkoxy-(C1-C4)-alkyl; R5 represents (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkyl; X1 represents N or CR6; X2 represents N or CR7; X3 represents N or CR8; R6 represents hydrogen, halogen, (C1-C3)-alkyl, (C1-C3)-alkoxy, (C2-C3)-alkenyl, (C2-C3)-alkynyl, halo-(C1-C3)-alkyl, halo-(C1-C3)-alkoxy; R7 represents hydrogen, halogen, (C1-C3)-alkyl; R8 represents hydrogen, hydroxy, halogen, cyano, nitro, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C3-C6)-cycloalkyl-(C1-C3)-alkyl, (C1-C6)-alkoxy-(C1-C3)-alkyl, (C1-C6)-alkoxy-(C2-C6)-alkoxy, (C1-C6)-alkoxy-(C2-C6)-alkoxy-(C1-C3)-alkyl, halo-(C1-C6)-alkoxy, halo-(C1-C6)-alkoxy-(C1-C3)-alkyl, (C1-C6)-alkyl-(O)nS, halo-(C1-C6)-alkyl-(O)nS, aryl, aryl-(O)nS, heterocyclyl, heterocyclyl-(O)nS, aryloxy, aryl-(C2-C6)-alkyl, aryl-(C1-C6)-alkoxy, heterocyclyloxy, heterocyclyl-(C1-C3)-alkoxy-(C1-C3)-alkyl, HO(O)C, HO(O)C—(C1-C3)-alkoxy, (C1-C3)-alkoxy-(O)C, (C1-C3)-alkoxy-(O)C—(C1-C3)-alkoxy, (C1-C3)-alkylamino, di-(C1-C3)-alkylamino, (C1-C3)-alkylamino-(O)nS, (C1-C3)-alkylamino-(O)nS—(C1-C3)-alkyl, di-(C1—C)-alkylamino-(O)nS, di-(C1-C3)-alkylamino-(O)nS—(C1-C3)-alkyl, (C1-C3)-alkylamino-(O)C, (C1-C3)-alkylamino-(O)C—(C1-C3)-alkyl, di-(C1-C3)-alkylamino-(O)C, di-(C1-C3)-alkylamino-(O)C—(C1-C3)-alkyl, (C1-C3)-alkyl-(O)C-amino, (C1-C3)-alkyl-(O)nS-amino, (C1-C3)-alkyl-(O)nS—(C1-C3)-alkylamino or (C1-C3)-alkyl-(O)nS-amino-(C1-C3)-alkyl, where the heterocyclyl groups and aryl groups are substituted by s radicals from the group consisting of (C1-C3)-alkyl, halo-(C1-C3)-alkyl, (C1-C3)-alkoxy, halo-(C1-C3)-alkoxy, (C1-C6)-alkyl-(O)nS, phenyl, cyano, nitro and halogen, or R7 and R8 together with the carbon atoms to which they are attached represent an unsaturated five- or six-membered ring which contains s nitrogen atoms and is substituted by s radicals R10; R9 represents halogen, (C1-C3)-alkyl, halo-(C1-C3)-alkyl, (C1-C6)-alkoxy, R10 represents cyano, halogen, (C1-C3)-alkyl-(O)nS, (C1-C3)-alkyl, (C2-C3)-alkenyl, (C2-C3)-alkynyl, halo-(C1-C3)-alkyl or morpholinyl; n represents 0, 1 or 2; s represents 0, 1, 2 or 3, with the proviso that R5 does not represent (C1-C6)-alkyl if A represents a direct bond.