Herbicidally active ketosultams and diketopyridines
Ketosultams and diketopyridines of the formula (I) and use thereof as herbicides are described. In this formula (I), G, X, Y and Z are each radicals such as hydrogen and organic radicals such as alkyl. W represents organic radicals such as alkyl. A represents a heterocycle.
1. A compound of formula (I) or a salt thereof
in which
A is one of the five-membered heterocycles A2 or A3 shown below, in which the broken lines mean the bond to the adjacent pyridine ring,
V is C(=0);
n is 0,1,2or 3;
G is hydrogen, C(=O)R 1 , C(=L)MR 2 , SO 2 R 3 , P(=L)R 4 R 5 , C(=L)NR 6 R 7 , E or R8;
E is a metal ion or an ammonium ion;
L is oxygen or sulfur;
M is oxygen or sulfur
R 1 is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkyl, di-(C 1 -C 4 )-alkoxy-(C 1 -C 6 ) -alkyl or (C 1 -C 4 )-alkylthio-(C 1 -C 6 )-alkyl each substituted by n halogen atoms,
a fully saturated 3- to 6-membered ring consisting of 3 to 5 carbon atoms and 1 to 3 heteroatoms from the group of oxygen, sulfur and nitrogen and substituted by n radicals from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxy,
(C 3 -C 6 )-cycloalkyl, phenyl, phenyl-(C 1 -C 4 )-alkyl, heteroaryl, phenoxy-(C 1 -C 4 )-alkyl or heteroaryloxy-(C 1 -C 4 )-alkyl substituted by n radicals from the group consisting of halogen, (C 1 -C 4 ) -alkyl and (C 1 -C 4 )-alkoxy;
R 2 is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkyl or di-(C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkyl each substituted by n halogen atoms,
or (C 3 -C 6 )-cycloalkyl, phenyl or benzyl substituted by n radicals in each case from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxy;
R 3 , R 4 and R 5 are each independently (C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkoxy, N-(C 1 -C 6 )-alkylamino, N,N-di-(C 1 -C 6 )-alkylamino, (C 1 -C 4 )-alkylthio, (C 2 -C 4 )-alkenyl or (C 3 -C 6 )-cycloalkylthio each substituted by n halogen atoms,
or phenyl, benzyl, phenoxy or phenylthio substituted by n radicals from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxy;
R 6 and R 7 are each independently hydrogen, (C 1 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 6 )-alkenyl, (C 1 -C 6 )-alkoxy or (C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkyl substituted by n halogen atoms,
phenyl or benzyl substituted by in each case n radicals from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxy,
or R 6 and R 7 form, together with the nitrogen atom to which they are bonded, a 3- to 6-membered ring containing 2 to 5 carbon atoms and 0 or 1 oxygen or sulfur atom;
R 8 is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 4 ) -alkylthio-(C 1 -C 4 )-alkyl or di-(C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkyl substituted by n halogen atoms,
(C 3 -C 6 )-cycloalkyl substituted by n radicals from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxy,
a fully saturated 3- to 6-membered ring consisting of 3 to 5 carbon atoms and 1 to 3 heteroatoms from the group of oxygen, sulfur and nitrogen and substituted by n radicals from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxy, phenyl, phenyl-(C 1 -C 4 )-alkyl, heteroaryl, phenoxy-(C 1 -C 4 )-alkyl or heteroaryloxy-(C 1 -C 4 )-alkyl substituted by n radicals from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxy;
R 10 is hydrogen, or (C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylsulfinyl or (C 1 -C 4 )-alkylsulfonyl substituted by n halogen atoms;
W is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 3 -C 6 )-alkenyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 6 ) -alkyl, di-(C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 4 ) -alkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkylsulfonyl-(C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl each substituted by n halogen atoms, and
X, Y and Z are each independently hydrogen, (C 1 -C 6 )-alkyl, halogen, cyano, nitro, halo-(C 1 -C 6 ) -alkyl, halo-(C 1 -C 6 )-alkoxy, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl.
2. A compound as claimed in claim 1 , in which
A is one of the five-membered heterocycles A2 to A3 shown below, in which the broken lines mean the bond to the adjacent pyridine or ketosultam ring,
V is C(=O);
n is 0,1,2or 3;
G is hydrogen;
W is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 3 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkyl, di-(C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 4 ) -alkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkylsulfonyl-(C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl each substituted by n halogen atoms;
X, Y and Z are each independently hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, halogen, cyano, nitro, halo-(C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl; and
R 1 ° is hydrogen, or (C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylsulfinyl or (C 1 -C 4 )-alkylsulfonyl substituted by n halogen atoms.
3. A compound as claimed in claim 1 , in which
A is one of the five-membered heterocycles A2 or A3 shown below, in which the broken lines mean the bond to the adjacent pyridine ring,
V is C(=O)
n is 0, 1, 2 or 3;
G is C(=O)R 1 ;
R 1 is (C 1 -C 6 )-alkyl each substituted by n halogen atoms;
W is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 3 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkoxy- (C 1 -C 6 )-alkyl, di-(C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 4 ) -alkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkylsulfonyl-(C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl each substituted by n halogen atoms; and
R 10 is hydrogen, or (C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylsulfinyl or (C 1 -C 4 )-alkylsulfonyl substituted by n halogen atoms.
4. A compound as claimed in claim 1 , in which
A is one of the five-membered heterocycles A2 or A3 shown below, in which the broken lines mean the bond to the adjacent pyridine ring,
V is C(=O;
n is 0,1,2or 3;
G is C(=L)MR 2 ;
L is oxygen;
M is oxygen or sulfur;
R 2 is (C 1 -C 6 )-alkyl each substituted by n halogen atoms;
W is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 3 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkyl, di-(C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 4 ) -alkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkylsulfonyl-(C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl each substituted by n halogen atoms and
X, Y and Z are each independently hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, halogen, cyano, nitro, halo-(C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )- alkyl, halo-(C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl; and
R 10 is hydrogen, or (C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylsulfinyl or (C 1 -C 4 )-alkylsulfonyl substituted by n halogen atoms.
5. A compound as claimed in claim 1 , in which
A is one of the five-membered heterocycles A2 or A3 shown below, in which the broken lines mean the bond to the adjacent pyridine ring,
V is C(=O);
n is 0,1,2or 3;
G is R 8 ;
R 8 is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl substituted by n halogen atoms;
W is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 3 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkyl, di-(C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 4 ) -alkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkylsulfonyl-(C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl each substituted by n halogen atoms;
X, Y and Z are each independently hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, halogen, cyano, nitro, halo-(C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl; and
R 10 is hydrogen, or (C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylsulfinyl or (C 1 -C 4 )-alkylsulfonyl substituted by n halogen atoms.
6. A herbicidal composition comprising a herbicidally active content of at least one compound as claimed in claim 1 .
7. The herbicidal composition as claimed in claim 6 in a mixture with one or more formulation assistants.