Bicyclic arylcarboxylic acid amides and their use as herbicides

Patent metadata

Field	Value
Publication number	US-9914710-B2
Application number	US-201515328253-A
Country	US
Kind code	B2
Filing date	Jul 24, 2015
Priority date	Jul 28, 2014
Publication date	Mar 13, 2018
Grant date	Mar 13, 2018

Abstract

Bicyclic arylcarboxamides of the general formula (I) are described as herbicides.

In this formula (I), Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are a bond, O, S(O) n or a substituted carbon atom. X is a radical such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen. Q is a substituted heterocycle.

First claim

The invention claimed is:

1. A bicyclic arylcarboxamide of the formula (I) or salt thereof

in which
A is N or CY,
X is nitro, halogen, cyano, formyl, thiocyanato, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 3 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, halo-(C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, COR 1 , COOR 1 , OCOOR 1 , NR 1 COOR 1 , C(O)N(R 1 ) 2 , NR 1 C(O)N(R 1 ) 2 , OC(O)N(R 1 ) 2 , C(O)NR 1 OR 1 , OR 1 , OCOR 1 , OSO 2 R 2 , S(O) n R 2 , SO 2 R 1 , SO 2 N(R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-OCOR 1 , (C 1 -C 6 )-alkyl-OSO 2 R 2 , (C 1 -C 6 )-alkyl-CO 2 R 1 , (C 1 -C 6 )-alkyl-SO 2 OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 , NR 1 R 2 , P(O)(OR 11 ) 2 , CH 2 P(O)(OR 11 ) 2 , (C 1 -C 6 )-alkylheteroaryl, (C 1 -C 6 )-alkylheterocyclyl, where the latter two radicals are each substituted by s radicals from the group consisting of halogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, S(O) n -(C 1- C 6 )-alkyl, (C 1 -C 6 )-alkoxy and halo-(C 1 -C 6 )-alkoxy, and where heterocyclyl bears n oxo groups,
Y is hydrogen, nitro, halogen, cyano, thiocyanato, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkenyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, halo-(C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, COR 1 , COOR 1 , OCOOR 1 , NR 1 COOR 1 , C(O)N(R 1 ) 2 , NR 1 C(O)N(R 1 ) 2 , OC(O)N(R 1 ) 2 , CO(NOR 1 )R 1 , C(NOR 1 )R 1 , NR 1 SO 2 R 2 , N═S(O)R 2 R 2 , NR 1 COR 1 , OR 1 , OSO 2 R 2 , S(O) n R 2 , S(O)(NR 2 )R 2 , SO2OR1, SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-OCOR 1 , (C 1 -C 6 )-alkyl-OSO2R 2 , (C 1 -C 6 )-alkyl-CO 2 R 1 , (C 1 -C 6 )-alkyl-CN, (C 1 -C 6 )-alkyl-SO 2 OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 , N(R 1 ) 2 , P(O)(OR 11 ) 2 , CH 2 P(O)(OR 11 ) 2 , (C 1 -C 6 )-alkylphenyl, (C 1 -C 6 )-alkylheteroaryl, (C 1 -C 6 )-alkylheterocyclyl, phenyl, heteroaryl or heterocyclyl, where the latter six radicals are each substituted by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy-(C 1 -C 4 )-alkyl and cyanomethyl, and where heterocyclyl bears n oxo groups,
R 1 is hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkenyl, (C 3 -C 6 )-halocycloalkyl, (C 1 -C 6 )-alkyl-O—(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl, phenyl-(C 1 -C 6 )-alkyl, heteroaryl, (C 1 -C 6 )-alkylheteroaryl, heterocyclyl, (C 1 -C 6 )-alkylheterocyclyl, (C 1 -C 6 )-alkyl-O-heteroaryl, (C 1 -C 6 )-alkyl-O-heterocyclyl, (C 1 -C 6 )-alkyl-NR 12 -heteroaryl or (C 1 -C 6 )-alkyl-NR 12 -heterocyclyl, where the latter 21 radicals are each substituted by s radicals from the group consisting of cyano, halogen, nitro, thiocyanato, OR 12 , S(O) n R 13 , N(R 12 ) 2 , NR 12 OR 12 , COR 12 , OCOR 12 , SCOR 13 , NR 12 COR 12 , NR 12 SO 2 R 13 , CO 2 R 12 , COSR 12 , CON(R 12 ) 2 , (C1-C6)-alkyl and (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl, and where heterocyclyl bears n oxo groups,
R 2 is (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkenyl, (C 3 -C 6 )-halocycloalkyl, (C 1 -C 6 )-alkyl-O—(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl, phenyl-(C 1 -C 6 )-alkyl, heteroaryl, (C 1 -C 6 )-alkylheteroaryl, heterocyclyl, (C 1 -C 6 )-alkylheterocyclyl, (C 1 -C 6 )-alkyl-O-heteroaryl, (C 1 -C 6 )-alkyl-O-heterocyclyl, (C 1 -C 6 )-alkyl-NR 3 -heteroaryl or (C 1 -C 6 )-alkyl-NR 3 -heterocyclyl, where the latter 21 radicals are each substituted by s radicals from the group consisting of cyano, halogen, nitro, thiocyanato, OR 12 , S(O) n R 13 , N(R 12 ) 2 , NR 12 OR 13 , COR 12 , OCOR 12 , SCOR 13 , NR 12 COR 12 , NR 12 SO 2 R 13 , CO 2 R 12 , COSR 13 , CON(R 12 ) 2 and (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl, and where heterocyclyl bears n oxo groups,
Q is a Q 1 , Q 2 , Q 3 or Q 4 radical,

R 3 is (C 1 -C 8 )-alkyl, (C 2 -C 8 )-alkenyl, (C 2 -C 8 )-alkynyl, where these radicals are each substituted by s radicals from the group consisting of halogen, cyano, hydroxyl, nitro, SiR 11 3 , PO(OR 11 ) 2 , S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, COR 3a , COOR 3a , OCOR 3a , NR 3a COR 3a , NR 3a SO 2 R 3b , (C 3 -C 6 )-cycloalkyl, heteroaryl, heterocyclyl or phenyl, where the latter 4 radicals are each substituted by s radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl, cyano and halogen, and where heterocyclyl bears n oxo groups,
or
R 3 is phenyl substituted by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n —(C 1 -C 6 -alkyl, (C 1 -C 6 ) -alkoxy, halo-(C 1 -C 6 )-alkoxy and (C 1 -C 6 )-alkoxy-(C 1 -C 4 )-alkyl,
R 3a is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl or phenyl,
R 3b is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 ) -cycloalkyl-(C 1 -C 6 )-alkyl or phenyl,
R 4 is hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkenyloxy, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )- alkynyl, (C 2 -C 6 )-alkynyloxy, (C 2 -C 6 )-haloalkynyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, or heteroaryl, heterocyclyl or phenyl, each substituted by s radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen,
R 5 is hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, CH 2 R 5a , (C 3 -C 7 )-cycloalkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 2 -C 6 )-alkynyl, (C 1 -C 6 )-alkoxy, methylamino, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methylcarbonyl, trifluoromethylcarbonyl, dimethylamino, acetylamino, methylsulfenyl, methylsulfinyl, methylsulfonyl, or heteroaryl, heterocyclyl, benzyl or phenyl, each substituted by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy and (C 1 -C 6 )-alkoxy-(C 1 -C 4 )-alkyl,
R 5a is acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylca

Assignees

• Bayer Cropscience Ag

Inventors

• Braun Ralf
• Waldraff Christian
• Dietrich Hansjörg
• Schmutzler Dirk
• Gatzweiler Elmar
• Rosinger Christopher Hugh

Classifications

• C07D257/06 Primary

  with nitrogen atoms directly attached to the ring carbon atom · CPC title

• A01N43/713

  having rings with four or more nitrogen atoms as the only ring hetero atoms · CPC title

• C07D409/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D405/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D271/08

  1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles · CPC title