US 2013/0274109 A1 · Substituted Pyrazines Having Herbicidal Activity

Substituted Pyrazines Having Herbicidal Activity

AssigneeBASF SE

InventorsRuediger Reingruber, Helmut Kraus, Johannes Hutzler, Trevor William Newton, Matthias Witschel, William Karl Moberg, Liliana Parra Rapado, Gilbert Besong, Michael Rack, Andree Van Der Kloet, Thomas Seitz, Jens Lerchl, Klaus Kreuz, Klaus Grossmann, Richard Roger Evans

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Abstract

The present invention provides substituted pyrazine compounds of the formula I or N-oxides or agriculturally suitable salts thereof, wherein the variables in the formula I are defined as in the description. Substituted pyrazines of formula I are useful as herbicides.

Claims21

Dependent claims

1-15. (canceled)

16:

A compound of formula I
wherein the variables have the following meaning:
R is O—RA, S(O)n—RA or O—S(O)n—RA;
RA is hydrogen, C1-C4-alkyl, Z—C3-C6-cycloalkyl, C1-C4-haloalkyl, C2-C6-alkenyl, Z—C3-C6-cycloalkenyl, C2-C6-alkynyl, Z-(tri-C1-C4-alkyl)silyl, Z—C(═O)—Ra, Z—NR1—C(O)—NRiRii, Z—P(═O)(Ra)2, NRiRii or 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, which may be partially or fully substituted by groups Ra and/or Rb,
Ra is 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 Rb;
Ri, Rii independently of one another are hydrogen, C1-C8-alkyl, C1-C4-haloalkyl, C3-C8-alkenyl, C3-C8-alkynyl, Z—C3-C6-cycloalkyl, Z—C1-C8-alkoxy, Z—C1-C8-haloalkoxy, Z—C(═O)—Ra, 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;
or
Ri and Rii together with the nitrogen atom to which they are attached may also form 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;
Z is a covalent bond or C1-C4-alkylene;
n is 0, 1 or 2;
R1 is cyano, halogen, nitro, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, Z—C1-C6-alkoxy, Z—C1-C4-alkoxy-C1-C4-alkoxy, Z—C1-C4-alkylthio, Z—C1-C4-alkylthio-C1-C4-alkylthio, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, C1-C4-haloalkoxy-C1-C4-alkoxy, S(O)nRbb, Z-phenoxy or Z-heterocyclyloxy, where heterocyclyl is a 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 Rb;
Rbb is C1-C8-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C2-C6-haloalknyl or C1-C6-haloalkyl and n is 0, 1 or 2;
A is N or C—R2;
R2 is Z1-heterocyclyl, where heterocyclyl is a 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 Rb;
or
is phenyl which is attached via Z1 or oxygen and is unsubstituted or substituted by C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl or C1-C4-alkoxy-C1-C4-alkoxy;
or
is C1-C8-alkyl, C2-C6-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C2-C8-haloalkenyl, C2-C8-haloalkynyl, C2-C6-alkoxy, Z—C1-C4-alkoxy-C1-C4-alkoxy, Z—C1-C4-haloalkoxy-C1-C4-alkoxy, Z—C1-C6-haloalkoxy, C2-C8s-alkenyloxy, C2-C8-alkynyloxy, Z—C1-C4-alkylthio, Z—C1-C6-haloalkylthio, Z—C(═O)—Ra or S(O)nRb;
Z1 is a covalent bond, C1-C4-alkyleneoxy, C1-C4-oxyalkylene or C1-C4-alkyleneoxy-C1-C4-alkylene;
Rb independently of one another are Z—CN, Z—OH, Z—NO2, Z-halogen, oxo (═O), ═N—Ra, C1-C8-alkyl, C1-C4-haloalkyl, C2-C8-alkenyl, C2-C8-alkynyl, Z—C1-C8-alkoxy, Z—C1-C8-haloalkoxy, Z—C3-C10-cycloalkyl, O—Z—C3-C10-cycloalkyl, Z—C(═O)—Ra, NRiRii, Z-(tri-C1-C4-alkyl)silyl, Z-phenyl or S(O)nRbb, where
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 additional groups Rb;
R3 is hydrogen, cyano, halogen, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C2-C4-alkenyloxy, C2-C4-alkynyloxy or S(O)nRb;
R4 is hydrogen, halogen or C1-C4-haloalkyl;
R5, R6 independently of one another are hydrogen, halogen or C1-C4-alkyl;
Rx, Ry independently of one another are hydrogen, C1-C8-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-C5-alkylene or C2-C8-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-C8-alkylene or C2-C8-alkenylene chain may be replaced by 1 or 2 heteroatoms independently selected from O or S;
where in the groups RA and their subsubtituents, the carbon chains and/or the cyclic groups may be partially or fully substituted by groups Rb,
or an N-oxide or an agriculturally suitable salt thereof.

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