US 11,834,434 B2
Substituted 2-heteroaryloxypyridines and salts thereof and their use as herbicidal agents
Michael Charles McLeod, Frankfurt (DE); Ralf Braun, Ramberg (DE); Anu Bheemaiah Machettira, Frankfurt am Main (DE); Dirk Schmutzler, Hattersheim (DE); Elisabeth Asmus, Hoesbach (DE); Christopher Hugh Rosinger, Hofheim (DE); and Elmar Gatzweiler, Bad Nauheim (DE)
Assigned to Bayer Aktiengesellschaft, Leverkusen (DE)
Appl. No. 17/255,770
Filed by Bayer Aktiengesellschaft, Leverkusen (DE)
PCT Filed Jun. 19, 2019, PCT No. PCT/EP2019/066197
§ 371(c)(1), (2) Date Dec. 23, 2020,
PCT Pub. No. WO2020/002089, PCT Pub. Date Jan. 2, 2020.
Claims priority of application No. 18179566 (EP), filed on Jun. 25, 2018.
Prior Publication US 2021/0276974 A1, Sep. 9, 2021
Int. Cl. A01N 43/54 (2006.01); C07D 401/12 (2006.01); A01N 43/40 (2006.01)
CPC C07D 401/12 (2013.01) [A01N 43/40 (2013.01); A01N 43/54 (2013.01)] 13 Claims
 
1. A substituted 2-heteroaryloxypyridine of formula (I) or a salt thereof

OG Complex Work Unit Chemistry
in which
X represents nitrogen, —CF— or —CH—,
A represents oxygen, —S(O)n—, —C(R4)(R5)—, —C(═O)— or —NR6— with n=0, 1 or 2,
R1 represents optionally substituted aryl, heteroaryl, heterocyclyl, (C3-C10)-cycloalkyl or (C3-C10)-cycloalkenyl, where each ring or each ring system is optionally substituted by up to 5 substituents independently selected from the group R7;
R2 independently of the others represents halogen, cyano, nitro, formyl, formamide, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkenyl, (C2-C8)-haloalkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C8)-alkylcarbonyl, (C1-C8)-haloalkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, carboxyl, (C1-C8)-alkoxycarbonyl, (C1-C8)-haloalkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, carbamoyl, (C2-C8)-alkylaminocarbonyl, (C2-C10)-dialkylaminocarbonyl, (C3-C10)-cycloalkylaminocarbonyl, (C1-C4)-alkoxycarbonyl-(C1-C4)-alkyl, (C1-C4)-haloalkoxycarbonyl-(C1-C4)-alkyl, carboxy-(C1-C4)-alkyl, hydroxy, amino, (C1-C8)-alkoxy, (C1-C8)-haloalkoxy, (C1-C8)-alkylthio, (C1-C8)-haloalkylthio, (C3-C8)-cycloalkylthio, (C1-C8)-alkylsulfinyl, (C1-C8)-haloalkylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C1-C8)-alkylsulfonyl, (C1-C8)-haloalkylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C1-C8)-alkylaminosulfonyl, (C2-C8)-dialkylaminosulfonyl or (C3-C8)-trialkylsilyl,
m represents 0, 1, 2 or 3,
R3 represents hydrogen, halogen, cyano, nitro, formyl, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkenyl, (C2-C8)-haloalkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C8)-alkylcarbonyl, (C1-C8)-haloalkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, carboxyl, (C1-C8)-alkoxycarbonyl, (C1-C8)-haloalkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C1-C8)-alkylaminocarbonyl, (C2-C8)-dialkylaminocarbonyl, (C3-C8)-cycloalkylaminocarbonyl, hydroxy, (C1-C8)-alkoxy, (C1-C8)-haloalkoxy, (C1-C8)-alkylthio, (C1-C8)-haloalkylthio, (C3-C8)-cycloalkylthio, (C1-C8)-alkylsulfinyl, (C1-C8)-haloalkylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C1-C8)-alkylsulfonyl, (C1-C8)-haloalkylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C1-C8)-alkylaminosulfonyl, (C2-C8)-dialkylaminosulfonyl or (C3-C8)-trialkylsilyl,
R4 and R5 independently of one another represent hydrogen, hydroxy, halogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C8)-alkylcarbonyl, (C1-C8)-haloalkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, (C1-C8)-alkoxycarbonyl, (C1-C8)-haloalkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C1-C8)-alkylaminocarbonyl, (C2-C8)-dialkylaminocarbonyl, (C3-C8)-cycloalkylaminocarbonyl, (C1-C8)-alkoxy, (C1-C8)-alkylthio, (C1-C8)-haloalkylthio, (C3-C8)-cycloalkylthio,
or
R4 and R5 together form a 3- to 6-membered carbocyclic ring or a 3- to 6-membered saturated heterocyclic ring having up to 2 oxygen atoms,
or
R4 and R5 together form a (C1-C3)-alkylidene radical or (C1-C3)-haloalkylidene radical,
R6 represents hydrogen, (C1-C8-alkyl, (C1-C8)-haloalkyl, aryl-(C1-C6)-alkyl, heteroaryl-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C3-C6)-halocycloalkyl, (C3-C6)-halocycloalkyl-(C1-C4)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C8)-alkylcarbonyl, (C1-C8-haloalkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, formyl, (C1-C8-alkoxycarbonyl, (C1-C8)-haloalkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C1-C8)-alkylaminocarbonyl, (C2-C8)-dialkylaminocarbonyl, (C3-C8)-cycloalkylaminocarbonyl,
and
R7 represents hydrogen, halogen, cyano, nitro, formyl, (C1-C8-alkyl, (C1-C8-haloalkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkenyl, (C2-C8)-haloalkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C8)-alkylcarbonyl, (C1-C8)-haloalkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, carboxyl, (C1-C8)-alkoxycarbonyl, (C1-C8-haloalkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C1-C8-alkylaminocarbonyl, (C2-C8)-dialkylaminocarbonyl, (C3-C8)-cycloalkylaminocarbonyl, hydroxy, (C1-C8)-alkoxy, (C1-C8)-haloalkoxy, (C1-C8)-alkylthio, (C1-C8)-haloalkylthio, (C3-C8)-cycloalkylthio, (C1-C8-alkylsulfinyl, (C1-C8)-haloalkylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C1-C8-alkylsulfonyl, (C1-C8)-haloalkylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C1-C8-alkylaminosulfonyl, (C2-C8)-dialkylaminosulfonyl or (C3-C8)-trialkylsilyl.