N-(1,2,5-oxadiazol-3-yl)pyridinecarboxamides and use thereof as herbicides
View Patent ↗A description is given of N-(1,2,5-oxadiazol-3-yl)pyridinecarboxamides of the general formula (I) as herbicides. R in this formula (I) stands for radicals such as hydrogen, organic radicals, and other radicals such as halogen. W stands for a substituted pyridyl radical.
1. An N-(1,2,5-oxadiazol-3-yl)pyridinecarboxamide of formula (I) and/or a salt thereof
in which
W is a W1, W2 or W3 group,
R is hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkenyloxy, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-alkynyloxy, (C 2 -C 6 )-haloalkynyl, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, (C 1 -C 6 )-alkylcarbonylamino, benzoylamino, phenoxy, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, or heteroaryl, heterocyclyl or phenyl each substituted by 0, 1, 2 or 3 radicals selected from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen,
X and V are each independently hydrogen, nitro, halogen, cyano, formyl, thiocyanato, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 3 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, halo-(C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, COR 1 , COOR 1 , OCOOR 1 , NR 1 COOR 1 , C(O)N(R 1 ) 2 , NR 1 C(O)N(R 1 ) 2 , OC(O)N(R 1 ) 2 , C(O)NR 1 OR 1 , OR 1 , OCOR 1 , OSO 2 R 2 , S(O) n R 2 , SO 2 OR 1 , SO 2 N(R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-OCOR 1 , (C 1 -C 6 )-alkyl-OSO 2 R 2 , (C 1 -C 6 )-alkyl-CO 2 R 1 , (C 1 -C 6 )-alkyl-SO 2 OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 , NR 1 R 2 , P(O)(OR 5 ) 2 , CH 2 P(O)(OR 5 ) 2 , (C 1 -C 6 )-alkylheteroaryl, (C 1 -C 6 )-alkylheterocyclyl, phenyl, heteroaryl or heterocyclyl, where the 5 latter radicals are each substituted by 0, 1, 2 or 3 radicals selected from the group consisting of halogen, nitro, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy-(C 1 -C 4 )-alkyl and cyanomethyl, and where heterocyclyl bears n oxo groups,
Y and U are each independently hydrogen, nitro, halogen, cyano, thiocyanato, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkenyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, halo-(C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, COR 1 , COOR 1 , OCOOR 1 , NR 1 COOR 1 , C(O)N(R 1 ) 2 , NR 1 C(O)N(R 1 ) 2 , OC(O)N(R 1 ) 2 , CO(NOR 1 )R 1 , NR 1 SO 2 R 2 , NR 1 COR 1 , OR 1 , OSO 2 R 2 , S(O) n R 2 , SO 2 OR 1 , SO 2 N(R 1 ) 2 (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-OCOR 1 , (C 1 -C 6 )-alkyl-OSO 2 R 2 , (C 1 -C 6 )-alkyl-CO 2 R 1 , (C 1 -C 6 )-alkyl-CN, (C 1 -C 6 )-alkyl-SO 2 OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 , N(R 1 ) 2 , P(O)(OR 5 ) 2 , CH 2 P(O)(OR 5 ) 2 , (C 1 -C 6 )-alkylphenyl, (C 1 -C 6 )-alkylheteroaryl, (C 1 -C 6 )-alkylheterocyclyl, phenyl, heteroaryl or heterocyclyl, where the 6 latter radicals are each substituted by at 0, 1, 2 or 3 radicals selected from the group consisting of halogen, nitro, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy-(C 1 -C 4 )-alkyl and cyanomethyl, and where heterocyclyl bears n oxo groups,
Z is hydrogen, halogen, cyano, thiocyanato, nitro, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkylthio, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, halo-(C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, COR 1 , COOR 1 , OCOOR 1 , NR 1 COOR 1 , C(O)N(R 1 ) 2 , NR 1 C(O)N(R 1 ) 2 , OC(O)N(R 1 ) 2 , C(O)NR 1 OR 1 , OSO 2 R 2 , S(O) n R2, SO 2 OR 1 , SO 2 N(R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-OCOR 1 , (C 1 -C 6 )-alkyl-OSO 2 R 2 , (C 1 -C 6 )-alkyl-CO 2 R 1 , (C 1 -C 6 )-alkyl-SO 2 OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 , N(R 1 ) 2 , P(O)(OR 5 ) 2 , heteroaryl, heterocyclyl or phenyl, where the three latter radicals are each substituted by 0, 1, 2 or 3 radicals selected from the group consisting of halogen, nitro, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy or halo-(C 1 -C 6 )-alkoxy, and where heterocyclyl bears n oxo groups,
R 1 is hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-halocycloalkyl, (C 1 -C 6 )-alkyl-O—(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl or phenyl-(C 1 -C 6 )-alkyl, where the 12 latter radicals are substituted by 0, 1, 2 or 3 radicals selected from the group consisting of cyano, halogen, nitro, thiocyanato, OR 3 , S(O) n R 4 , N(R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , SCOR 3 , NR 3 COR 3 , CO 2 R 3 , COSR 3 , CON(R 3 ) 2 and (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl,
R 2 is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl or phenyl-(C 1 -C 6 )-alkyl, where the seven latter radicals are substituted by 0, 1, 2 or 3 radicals selected from the group consisting of cyano, halogen, nitro, thiocyanato, OR 3 , S(O) n R 4 , N(R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , SCOR 3 , NR 3 COR 3 , CO 2 R 3 , COSR 3 , CON(R 3 ) 2 and (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl,
R 3 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl,
R 4 is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl,
R 5 is methyl or ethyl,
n is 0, 1 or 2,
with the proviso that the substituents U, V, X and Z in W1 or the substituents U, V, X and Y in W2 are not all simultaneously hydrogen.
2. An N-(1,2,5-oxadiazol-3-yl)pyridinecarboxamide and/or salt thereof as claimed in claim 1 , in which
W is a W1, W2 or W3 group,
R is (C 1 -C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, (C 1 -C 4 )-alkylcarbonylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, benzoyl, phenoxy, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, 1,2,4-triazol-1H, 1-pyrazol-1H, 2-thiophenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1,2,4-oxadiazol-3-yl, benzoxazol-2-yl, 1-ethylbenzimidazol-2-yl, piperidin-1-yl, or phenyl, where the 11 latter radicals are each substituted by 0, 1, 2 or 3 radicals selected from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen,
X and V are each independently hydrogen, nitro, halogen, cyano, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 6 )-cycloalkyl, OR 1 , S(O) n R 2 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 or (C 1 -C 6 )-alkylheteroaryl, (C 1 -C 6 )-alkylheterocyclyl, where the 2 latter radicals are each substituted by 0, 1, 2 or 3 radicals selected from the group consisting of halogen, nitro, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy-(C 1 -C 4 )-alkyl and cyanomethyl, and where heterocyclyl bears n oxo groups,
Y and U are each independently hydrogen, nitro, halogen, cyano, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, halo-(C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkylthio, OR 1 , S(O) n R 2 , SO 2 N(R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 )-alkyl-S(O) n R 2 or (C 1 -C 6 )-alkyl-OR 1 ,
Z is hydrogen, halogen, cyano, nitro, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkoxy, (C 3 -C 6 )-cycloalkyl, COR 1 , COOR 1 , NR 1 COOR 1 , C(O)N(R 1 ) 2 , OSO 2 R 2 , S(O) n R 2 , SO 2 N(R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-CO 2 R 1 , (C 1 -C 6 )-alkyl-SO 2 OR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 , N(R 1 ) 2 , heteroaryl or heterocyclyl, where the two latter radicals are each substituted by 0, 1, 2 or 3 radicals selected from the group consisting of halogen, nitro, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy or halo-(C 1 -C 6 )-alkoxy, and where heterocyclyl bears n oxo groups,
R 1 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl or phenyl-(C 1 -C 6 )-alkyl, where the seven latter radicals are substituted by 0, 1, 2 or 3 radicals selected from the group consisting of halogen and OR 3 ,
R 2 is (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, where the three latter radicals are each substituted by 0, 1, 2 or 3 radicals selected from the group consisting of halogen and OR 3 ,
R 3 is hydrogen or (C 1 -C 6 )-alkyl,
n is 0, 1 or 2,
with the proviso that the substituents U, V, X and Z in W1 or the substituents U, V, X and Y in W2 are not all simultaneously hydrogen.
3. An N-(1,2,5-oxadiazol-3-yl)pyridinecarboxamide and/or salt thereof as claimed in claim 1 , in which
W is a W1, W2 or W3 group,
R is (C 1 -C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, (C 1 -C 4 )-alkylcarbonylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, benzoyl, phenoxy, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, 1,2,4-triazol-1H, 1-pyrazol-1H, 2-thiophenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1,2,4-oxadiazol-3-yl, benzoxazol-2-yl, 1-ethylbenzimidazol-2-yl, piperidin-1-yl, or phenyl, where the 11 latter radicals are each substituted by 0, 1, 2 or 3 radicals selected from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen,
X and V are each independently hydrogen, nitro, halogen, cyano, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 6 )-cycloalkyl, OR 1 , S(O) n R 2 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 or (C 1 -C 6 )-alkylheteroaryl, (C 1 -C 6 )-alkylheterocyclyl, where the 2 latter radicals are each substituted by 0, 1, 2 or 3 radicals selected from the group consisting of halogen, nitro, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy-(C 1 -C 4 )-alkyl and cyanomethyl, and where heterocyclyl bears n oxo groups,
Y and U are each independently hydrogen, nitro, halogen, cyano, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, halo-(C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkylthio, OR 1 , S(O) n R 2 , SO 2 N(R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 )-alkyl-S(O) n R 2 or (C 1 -C 6 )-alkyl-OR 1 ,
Z is hydrogen, halogen, cyano, nitro, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkoxy, (C 3 -C 6 )-cycloalkyl, COR 1 , COOR 1 , NR 1 COOR 1 , C(O)N(R 1 ) 2 , OSO 2 R 2 , S(O) n R 2 , SO 2 N(R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-CO 2 R 1 , (C 1 -C 6 )-alkyl-SO 2 OR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 , N(R 1 ) 2 , heteroaryl or heterocyclyl, where the two latter radicals are each substituted by 0, 1, 2 or 3 radicals selected from the group consisting of halogen, nitro, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy or halo-(C 1 -C 6 )-alkoxy, and where heterocyclyl bears n oxo groups,
R 1 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl or phenyl-(C 1 -C 6 )-alkyl, where the seven latter radicals are substituted by 0, 1, 2 or 3 radicals selected from the group consisting of halogen and OR 3 ,
R 2 is (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, where the three latter radicals are each substituted by 0, 1, 2 or 3 radicals selected from the group consisting of halogen and OR 3 ,
R 3 is hydrogen or (C 1 -C 6 )-alkyl,
n is 0, 1 or 2,
and in which 2 substituents from the group of U, V, X, Y and Z are each hydrogen, with the proviso that the substituents U, V, X and Z in W1 or the substituents U, V, X and Y in W2 are not all simultaneously hydrogen.
4. An N-(1,2,5-oxadiazol-3-yl)pyridinecarboxamide and/or salt thereof as claimed in any of claim 1 , in which
W is a W1 group,
R is (C 1 -C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, (C 1 -C 4 )-alkylcarbonylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, benzoyl, phenoxy, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, 1,2,4-triazol-1H, 1-pyrazol-1H, 2-thiophenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1,2,4-oxadiazol-3-yl, benzoxazol-2-yl, 1-ethylbenzimidazol-2-yl, piperidin-1-yl, or phenyl, where the 11 latter radicals are each substituted by 0, 1, 2 or 3 radicals selected from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen,
X and V are each independently hydrogen, nitro, halogen, cyano, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 6 )-cycloalkyl, OR 1 , S(O) n R 2 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 or (C 1 -C 6 )-alkylheteroaryl, (C 1 -C 6 )-alkylheterocyclyl, where the 2 latter radicals are each substituted by 0, 1, 2 or 3 radicals selected from the group of halogen, nitro, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy-(C 1 -C 4 )-alkyl and cyanomethyl, and where heterocyclyl bears n oxo groups,
U is hydrogen, nitro, halogen, cyano, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, halo-(C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkylthio, OR 1 , S(O) n R 2 , SO 2 N(R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 )-alkyl-S(O) n R 2 or (C 1 -C 6 )-alkyl-OR 1 ,
Z is hydrogen, halogen, cyano, nitro, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkoxy, (C 3 -C 6 )-cycloalkyl, COR 1 , COOR 1 , NR 1 COOR 1 , C(O)N(R 1 ) 2 , OSO 2 R 2 , S(O) n R 2 , SO 2 N(R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-CO 2 R 1 , (C 1 -C 6 )-alkyl-SO 2 OR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 , N(R 1 ) 2 , heteroaryl or heterocyclyl, where the two latter radicals are each substituted by 0, 1, 2 or 3 radicals selected from the group consisting of halogen, nitro, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy or halo-(C 1 -C 6 )-alkoxy, and where heterocyclyl bears n oxo groups,
R 1 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl or phenyl-(C 1 -C 6 )-alkyl, where the seven latter radicals are substituted by 0, 1, 2 or 3 radicals selected from the group consisting of halogen and OR 3 ,
R 2 is (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, where the three latter radicals are substituted by 0, 1, 2 or 3 radicals selected from the group consisting of halogen and OR 3 ,
R 3 is hydrogen or (C 1 -C 6 )-alkyl,
n is 0, 1 or 2,
and in which 2 substituents from the group of U, V, X, Y and Z are each hydrogen, with the proviso that the substituents X, Z, U and V are not all simultaneously hydrogen.
5. A herbicidal composition, comprising a herbicidally active content of at least one compound of formula (I) and/or salt thereof as claimed in claim 1 .
6. The herbicidal composition as claimed in claim 5 , in a mixture with at least one formulation auxiliary.
7. The herbicidal composition as claimed in claim 5 , comprising at least one further active substance selected from the group consisting of an insecticide, an acaricide, a herbicide, a fungicide, a safener and a growth regulator.
8. The herbicidal composition as claimed in claim 7 , comprising a safener.
9. The herbicidal composition as claimed in claim 8 , comprising a cyprosulfamide, a cloquintocet-mexyl, a mefenpyr-diethyl or a isoxadifen-ethyl.
10. The herbicidal composition as claimed in claim 7 , comprising a further herbicide.
11. A method for controlling an unwanted plant, comprising applying an effective amount of at least one compound of formula (I) and/or salt thereof as claimed in claim 1 , to a plant and/or a site of an unwanted vegetation.
12. A compound of formula (I) and/or salt thereof as claimed in claim 1 , capable of being used for controlling an unwanted plant.
13. A compound of formula (I) and/or salt thereof as claimed in claim 12 , wherein said compound of formula (I) is capable of being used for controlling an unwanted plant in a crop of a useful plant.
14. A compound of formula (I) and/or salt thereof as claimed in claim 13 , wherein said useful plant is a transgenic useful plant.
15. A method for controlling an unwanted plant, comprising applying an effective amount of a herbicidal composition as claimed in claim 5 , to a plant and/or a site of an unwanted vegetation.
16. An herbicidal composition as claimed in claim 5 , capable of being used for controlling an unwanted plant.
17. An N-(1,2,5-oxadiazol-3-yl)pyridinecarboxamide and/or salt thereof as claimed in claim 1 , in which W is
18. An N-(1,2,5-oxadiazol-3-yl)pyridinecarboxamide and/or salt thereof as claimed in claim 1 , in which W is
19. An N-(1,2,5-oxadiazol-3-yl)pyridinecarboxamide and/or salt thereof as claimed in claim 1 , in which W is