US 2016/0102103 A1 · SUBSTITUTED PYRIDINE COMPOUNDS HAVING HERBICIDAL ACTIVITY

1-15. (canceled)

16:

A substituted pyridine compound of the formula I
wherein
R is hydroxy or O—RA, where RA is C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, aryl-C1-C4-alkyl, C1-C8-alkylcarbonyl, C1-C8-alkoxycarbonyl, C1-C8-alkylthiocarbonyl, C1-C8-alkylsulfonyl, —C(O)—NRiRii or —CH2OC(O)—C1-C8-alkyl, where the aryl moiety is unsubstituted or substituted by one to five Ra and each Ra is independently halogen, cyano, nitro, C1-C8-alkyl, C1-C8-haloalkyl, C1-C8-alkoxy or C1-C8-haloalkoxy;
R1 is cyano, halogen, nitro, C1-C6-alkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, O—Z—C3-C10-cycloalkyl, C1-C6-alkyl-C3-C10-cycloalkyl, C1-C6-alkyl-C3-C10-halocycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C6-haloalkynyl, Z—C1-C6-alkoxy, Z—C1-C4-alkoxy-C1-C4-alkoxy, Z—C1-C4-alkylthio, Z—C1-C4-haloalkylthio, Z—C1-C4-alkylthio-C1-C4-alkylthio, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, C1-C4-haloalkoxy-C1-C4-alkoxy, S(O)nRb, Z-phenoxy, Z-heterocyclyl or Z-heterocyclyloxy, where heterocyclyl is a 4-, 5- or 6-membered monocyclic or 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where the cyclic groups are unsubstituted or partially or fully substituted by Rc;
Z is independently a covalent bond or C1-C4-alkylene;
n is independently 0, 1 or 2;
Rb is independently C1-C8-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C3-C6-haloalkynyl, C1-C6-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C3-C10-cycloalkyl, C1-C6-alkyl-C3-C10-cycloalkyl, heterocyclyl, C1-C6-alkyl-heterocyclyl, C1-C6-alkyloxyheterocyclyl or NRiRii, where heterocyclyl is a 4-, 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where the cyclic groups are unsubstituted or partially or fully substituted by Rc;
Rc is independently Z—CN, Z—OH, Z—NO2, Z-halogen, oxo (═O), ═N—Rd, C1-C8-alkyl, C1-C4-haloalkyl, C2-C8-alkenyl, C2-C8-alkynyl, Z—C1-C8-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy, Z—C1-C8-haloalkoxy, Z—C3-C10-cycloalkyl, O—Z—C3-C10-cycloalkyl, Z—C(═O)—Rd, NRiRii, Z-(tri-C1-C4-alkyl)silyl, Z-phenyl or S(O)nRb;
or two groups Rc may together form a ring which has 3 to 6 ring members and, in addition to carbon atoms, may contain heteroatoms selected from the group consisting of O, N and S and may be unsubstituted or substituted by further groups Rc;
Rd is independently hydrogen, OH, C1-C8-alkyl, C1-C4-haloalkyl, Z—C3-C6-cycloalkyl, C2-C8-alkenyl, Z—C5-C6-cycloalkenyl, C2-C8-alkynyl, Z—C1-C6-alkoxy, Z—C1-C4-haloalkoxy, Z—C3-C8-alkenyloxy, Z—C3-C8-alkynyloxy, NRiRii, C1-C6-alkylsulfonyl, Z-(tri-C1-C4-alkyl)silyl, Z-phenyl, Z-phenoxy, Z-phenylamino or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where the cyclic groups are unsubstituted or substituted by 1, 2, 3 or 4 groups Rc;
Ri, Rii independently of one another are hydrogen, C1-C8-alkyl, C1-C4-haloalkyl, C2-C8-alkenyl, C2-C8-alkynyl, Z—C3-C6-cycloalkyl, Z—C1-C8-alkoxy, Z—C1-C8-haloalkoxy, Z—C(═O)—Rd, Z-phenyl, a 3- to 7-membered monocyclic or 9- or 10-membered bicyclic saturated, unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S and which is attached via Z;
Ri and Rii together with the atom or atoms to which they are attached may also form a 3-, 4-, 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S;
R2, R3 independently of one another are hydrogen, Z-halogen, Z—CN, Z—OH, Z—NO2, C1-C8-alkyl, C1-C4-haloalkyl, C2-C8-alkenyl, C2—C-alkynyl, C2-C8-haloalkenyl, C2-C8-haloalkynyl, Z—C1-C8-alkoxy, Z—C1-C8-haloalkoxy, Z—C1-C4-alkoxy-C1-C4-alkoxy, Z—C1-C4-alkythio, Z—C1-C4-alkylthio-C1-C4-alkylthio, Z—C1-C6-haloalkylthio, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkenyloxy, C2-C6-haloalkynyloxy, C1-C4-haloalkoxy-C1-C4-alkoxy, Z—C3-C10-cycloalkyl, O—Z—C3-C10-cycloalkyl, C1-C6-alkyl-C3-C10-cycloalkyl, Z1—C3-C10-cycloalkyl, Z1—C(O)NRiRii, Z1—SO2NRiRii, Z1—RiCORii, Z1—NRiSO2Rii, Z—C(═O)—Rd, NRiRii, Z-(tri-C1-C4-alkyl)silyl, S(O)nRb, NRiSO2Rii, NRiCO2Rii, NRiCORii, NRiCONRiRii, Z—S(O)nNRiRii, Z—NRiCORii, Z—NRiSO2Rii Z-phenyl, Z1-phenyl, Z-heterocyclyl or Z1-heterocyclyl, where heterocyclyl is a 4-, 5- or 6-membered monocyclic or 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where cyclic groups are unsubstituted or partially or fully substituted by Re;
R2 together with the group attached to the adjacent carbon atom may also form a 5- to 10-membered saturated or partially or fully unsaturated mono- or bicyclic ring which, in addition to carbon atoms, may contain 1, 2 or 3 heteroatoms selected from the group consisting of O, N and S and may be substituted by further groups Rc;
Z1 is independently a covalent bond, C1-C4-alkyleneoxy, C1-C4-oxyalkylene or C1-C4-alkyleneoxy-C1-C4-alkylene;
R4, R5, R6, R7 independently of one another are hydrogen, halogen, C1-C4-alkyl or C3-C10-cycloalkyl;
Rx, Ry independently of one another are hydrogen, C1-C5-alkyl, C2-C5-alkenyl, C2-C5-alkynyl, C1-C8-haloalkyl, C1-C2-alkoxy-C1-C2-alkyl or halogen;
or Rx and Ry are together a C2-C8-alkylene or C2-C5-alkenylene chain and form a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or fully unsaturated monocyclic ring together with the carbon atom they are bonded to, wherein 1 or 2 of any of the CH2 or CH groups in the C2-C5-alkylene or C2-C5-alkenylene chain may be replaced by 1 or 2 heteroatoms independently selected from O or S;
where in the groups R1, R2 and R3 and their subsubstituents, the carbon chains and/or the cyclic groups may be partially or fully substituted by groups Rc,
or an agriculturally suitable salt or N-oxide thereof.

17 more elements

Substituted pyridine compounds having herbicidal activity

Life of this patent

Abstract

Claims28

Substituted pyridine compounds having herbicidal activity

Life of this patent

Abstract

Claims28