Herbicidally active ketosultams and diketopyridines
AssigneeBayer CropScience AG
InventorsStefan LEHR, Christian WALDRAFF, Elmar GATZWEILER, Isolde HÄUSER-HAHN, Ines HEINEMANN, Christopher Hugh ROSINGER
Life of this patent
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Abstract
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.
Claims16
A compound comprising a ketosultam or diketopyridine of the formula (I) and/or a salt thereof
- in which
- A is a fused-on saturated or unsaturated five-membered heterocycle substituted by m radicals selected from the group consisting of R10, R11, R12, R13 and R14;
- V is C(═O) or S(O)2;
- m is 0, 1 or 2;
- n is 0, 1, 2 or 3;
- G is hydrogen, C(═O)R1, C(=L)MR2, SO2R3, P(=L)R4R5, C(=L)NR6R7, E or R8;
- E is a metal ion equivalent or an ammonium ion;
- L is oxygen or sulfur;
- M is oxygen or sulfur;
- R1 is (C1-C6)-alkyl, (C2-C6)-alkenyl, (C1-C4)-alkoxy-(C1-C6)-alkyl, di-(C1-C4)-alkoxy-(C1-C6)-alkyl or (C1-C4)-alkylthio-(C1-C6)-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, (C1-C4)-alkyl and (C1-C4)-alkoxy, (C3-C6)-cycloalkyl, phenyl, phenyl-(C1-C4)-alkyl, phenoxy-(C1-C4)-alkyl or heteroaryl-oxy-(C1-C4)-alkyl substituted by n radicals from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-alkoxy;
- R2 is (C1-C6)-alkyl, (C2-C6)-alkenyl, (C1-C4)-alkoxy-(C1-C6)-alkyl or di-(C1-C4)-alkoxy-(C1-C6)-alkyl each substituted by n halogen atoms,
- or (C3-C6)-cycloalkyl, phenyl or benzyl substituted by n radicals in each case from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-alkoxy;
- R3, R4 and R5 are each independently (C1-C6)-alkyl, (C1-C4)-alkoxy, N—(C1-C6)-alkylamino, N,N-di-(C1-C6)-alkylamino, (C1-C4)-alkylthio, (C2-C4)-alkenyl or (C3-C6)-cycloalkylthio each substituted by n halogen atoms,
- or phenyl, benzyl, phenoxy or phenylthio substituted by n radicals from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-alkoxy;
- R6 and R7 are each independently hydrogen,
- (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C1-C6)-alkoxy or (C1-C4)-alkoxy-(C1-C6)-alkyl substituted by n halogen atoms,
- phenyl or benzyl substituted by in each case n radicals from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-alkoxy,
- or R6 and R7 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;
- R8 is (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C4)-alkoxy-(C1-C6)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl or di-(C1-C4)-alkoxy-(C1-C6)-alkyl substituted by n halogen atoms,
- (C3-C6)-cycloalkyl substituted by n radicals from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-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, (C1-C4)-alkyl and (C1-C4)-alkoxy, phenyl, phenyl-(C1-C4)-alkyl, heteroaryl, phenoxy-(C1-C4)-alkyl or heteroaryloxy-(C1-C4)-alkyl substituted by n radicals from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-alkoxy;
- R10 is hydrogen, or (C1-C6)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylsulfinyl or (C1-C4)-alkylsulfonyl substituted by n halogen atoms;
- R11, R12 and R13 are each independently hydrogen, halogen, or (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C4)-alkoxy-(C1-C6)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, di-(C1-C4)-alkoxy-(C1-C6)-alkyl, (C1-C4)-alkylthio, (C1-C4)-alkylsulfinyl or (C1-C4)-alkylsulfonyl substituted by n halogen atoms, or
- (C3-C6)-cycloalkyl substituted by n radicals from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-alkoxy;
- R14 is hydrogen, or (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C4)-alkoxy-(C1-C6)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl or di-(C1-C4)-alkoxy-(C1-C6)-alkyl substituted by n halogen atoms, or (C1-C6)-alkylcarbonyl, (C1-C6)-alkoxycarbonyl, (C1-C6)-alkylsulfonyl, or
- (C3-C6)-cycloalkyl, (C3-C6)-cycloalkylcarbonyl, (C3-C6)-cycloalkoxycarbonyl, (C3-C6)-cycloalkylsulfonyl substituted by n radicals from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-alkoxy;
- W is (C1-C6)-alkyl, (C2-C6)-alkenyl, (C3-C6)-alkynyl, (C3-C6)-cycloalkyl, (C1-C4)-alkoxy-(C1-C6)-alkyl, di-(C1-C4)-alkoxy-(C1-C6)-alkyl, (C1-C4)-alkylthio-(C1-C6)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C6)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C6)-alkyl or (C3-C6)-cycloalkyl-(C1-C6)-alkyl each substituted by n halogen atoms, and
- X, Y and Z are each independently hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, halogen, cyano, nitro, halo-(C1-C6)-alkyl, halo-(C1-C6)-alkoxy, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, (C1-C6)-alkoxy-(C1-C6)-alkyl, halo-(C1-C6)-alkoxy-(C1-C6)-alkyl.
A method for controlling unwanted plants, comprising applying an effective amount of at least one compound as claimed in claim to the plants and/or to a site of unwanted plant growth.
A compound of the formula (II)
- A is a fused-on saturated or unsaturated five-membered heterocycle substituted by m radicals selected from the group consisting of R10, R11, R12, R13 and R14;
- V is C(═O) or S(O)2;
- m is 0, 1 or 2;
- n is 0, 1, 2 or 3;
- G is hydrogen, C(═O)R1, C(=L)MR2, SO2R3, P(=L)R4R5, C(=L)NR6R7, E or R8;
- E is a metal ion equivalent or an ammonium ion;
- L is oxygen or sulfur;
- M is oxygen or sulfur;
- R1 is (C1-C6)-alkyl, (C2-C6)-alkenyl, (C1-C4)-alkoxy-(C1-C6)-alkyl, di-(C1-C4)-alkoxy-(C1-C6)-alkyl or (C1-C4)-alkylthio-(C1-C6)-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, (C1-C4)-alkyl and (C1-C4)-alkoxy, (C3-C6)-cycloalkyl, phenyl, phenyl-(C1-C4)-alkyl, phenoxy-(C1-C4)-alkyl or heteroaryl-oxy-(C1-C4)-alkyl substituted by n radicals from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-alkoxy;
- R2 is (C1-C6)-alkyl, (C2-C6)-alkenyl, (C1-C4)-alkoxy-(C1-C6)-alkyl or di-(C1-C4)-alkoxy-(C1-C6)-alkyl each substituted by n halogen atoms,
- or (C3-C6)-cycloalkyl, phenyl or benzyl substituted by n radicals in each case from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-alkoxy;
- R3, R4 and R5 are each independently (C1-C6)-alkyl, (C1-C4)-alkoxy, N—(C1-C6)-alkylamino, N,N-di-(C1-C6)-alkylamino, (C1-C4)-alkylthio, (C2-C4)-alkenyl or (C3-C6)-cycloalkylthio each substituted by n halogen atoms,
- or phenyl, benzyl, phenoxy or phenylthio substituted by n radicals from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-alkoxy;
- R6 and R7 are each independently hydrogen,
- (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C1-C6)-alkoxy or (C1-C4)-alkoxy-(C1-C6)-alkyl substituted by n halogen atoms,
- phenyl or benzyl substituted by in each case n radicals from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-alkoxy,
- or R6 and R7 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;
- R8 is (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C4)-alkoxy-(C1-C6)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl or di-(C1-C4)-alkoxy-(C1-C6)-alkyl substituted by n halogen atoms,
- (C3-C6)-cycloalkyl substituted by n radicals from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-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, (C1-C4)-alkyl and (C1-C4)-alkoxy, phenyl, phenyl-(C1-C4)-alkyl, heteroaryl, phenoxy-(C1-C4)-alkyl or heteroaryloxy-(C1-C4)-alkyl substituted by n radicals from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-alkoxy;
- R10 is hydrogen, or (C1-C6)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylsulfinyl or (C1-C4)-alkylsulfonyl substituted by n halogen atoms;
- R11, R12 and R13 are each independently hydrogen, halogen, or (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C4)-alkoxy-(C1-C6)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, di-(C1-C4)-alkoxy-(C1-C6)-alkyl, (C1-C4)-alkylthio, (C1-C4)-alkylsulfinyl or (C1-C4)-alkylsulfonyl substituted by n halogen atoms, or
- (C3-C6)-cycloalkyl substituted by n radicals from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-alkoxy;
- R14 is hydrogen, or (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C4)-alkoxy-(C1-C6)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl or di-(C1-C4)-alkoxy-(C1-C6)-alkyl substituted by n halogen atoms, or (C1-C6)-alkylcarbonyl, (C1-C6)-alkoxycarbonyl, (C1-C6)-alkylsulfonyl, or
- (C3-C6)-cycloalkyl, (C3-C6)-cycloalkylcarbonyl, (C3-C6)-cycloalkoxycarbonyl, (C3-C6)-cycloalkylsulfonyl substituted by n radicals from the group consisting of halogen, (C1-C4)-alkyl and (C1-C4)-alkoxy;
- W is (C1-C6)-alkyl, (C2-C6)-alkenyl, (C3-C6)-alkynyl, (C3-C6)-cycloalkyl, (C1-C4)-alkoxy-(C1-C6)-alkyl, di-(C1-C4)-alkoxy-(C1-C6)-alkyl, (C1-C4)-alkylthio-(C1-C6)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C6)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C6)-alkyl or (C3-C6)-cycloalkyl-(C1-C6)-alkyl each substituted by n halogen atoms, and
- X, Y and Z are each independently hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, halogen, cyano, nitro, halo-(C1-C6)-alkyl, halo-(C1-C6)-alkoxy, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, (C1-C6)-alkoxy-(C1-C6)-alkyl, halo-(C1-C6)-alkoxy-(C1-C6)-alkyl.
Dependencies are inferred from the claim text.