Substituted ketoxime benzoylamides

Patent metadata

Field	Value
Publication number	US-10785979-B2
Application number	US-201615754313-A
Country	US
Kind code	B2
Filing date	Aug 22, 2016
Priority date	Aug 25, 2015
Publication date	Sep 29, 2020
Grant date	Sep 29, 2020

Abstract

In this formula (I), R1′, R2′, X, Y and W are radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen. Q is an oxadiazole, tetrazole or triazole radical.

First claim

The invention claimed is:

1. A substituted ketoxime benzoylamide of formula (I)

in which
Q is a Q1, Q2, Q3 or Q4 radical

R is hydrogen, (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, R 1 (O)C—(C 1 -C 6 )-alkyl, R 1 O(O)C—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O)C—(C 1 -C 6 )-alkyl, NC—(C 1 -C 6 )-alkyl, R 1 O—(C 1 -C 6 )-alkyl, R 1 (O)CO—(C 1 -C 6 )-alkyl, R 1 O(O)C—O—(C 1 -C 6 )-alkyloxy, R 2 (O) 2 SO—(C 1 -C 6 )-alkyl, (R 1 ) 2 N—(C 1 -C 6 )-alkyl, R 1 (O)C(R 1 )N—(C 1 -C 6 )-alkyl, R 2 (O) 2 S(R)N—(C 1 -C 6 )-alkyl, R 2 (O) n S—(C 1 -C 6 )-alkyl, R 1 O(O) 2 S—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O) 2 S—(C 1 -C 6 )-alkyl, R 1 (O)C, R 1 O(O)C, (R 1 ) 2 N(O)C, R 10 , (R 1 ) 2 N, R 1 O(O)C(R 1 )N, (R 1 ) 2 N(O)C(R 1 )N, R 2 (O) 2 S, or benzyl substituted in each case by s radicals selected from the group consisting of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen,
R 1 is hydrogen, (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, (C 3 -C 6 )-cycloalkenyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyl-O—(C 1 -C 6 )-alkyl, cycloalkyl-(C 1 -C 6 )-alkyl-O—(C 1 -C 6 )-alkyl, phenyl, phenyl-(C 1 -C 6 )-alkyl, heteroaryl, heteroaryl-(C 1 -C 6 )-alkyl, heterocyclyl, heterocyclyl-(C 1 -C 6 )-alkyl, phenyl-O—(C 1 -C 6 )-alkyl, heteroaryl-O—(C 1 -C 6 )-alkyl, heterocyclyl-O—(C 1 -C 6 )-alkyl, phenyl-N(R 3 )—(C 1 -C 6 )-alkyl, heteroaryl-N(R 3 )—(C 1 -C 6 )-alkyl, heterocyclyl-N(R 3 )—(C 1 -C 6 )-alkyl, phenyl-S(O) n —(C 1 -C 6 )-alkyl, heteroaryl-S(O) n —(C 1 -C 6 )-alkyl or heterocyclyl-S(O) n —(C 1 -C 6 )-alkyl, where the fifteen latter radicals are each substituted by s radicals selected from the group consisting of nitro, halogen, cyano, thiocyanato, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, R 3 O(O)C, (R 3 ) 2 N(O)C, R 3 O, (R 3 ) 2 N, R 4 (O) n S, R 3 O(O) 2 S, (R 3 ) 2 N(O) 2 S and R 3 O—(C 1 -C 6 )-alkyl, and where heterocyclyl bears n oxo groups,
R 2 is (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, (C 3 -C 6 )-cycloalkenyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyl-O—(C 1 -C 6 )-alkyl, cycloalkyl-(C 1 -C 6 )-alkyl-O—(C 1 -C 6 )-alkyl, phenyl, phenyl-(C 1 -C 6 )-alkyl, heteroaryl, heteroaryl-(C 1 -C 6 )-alkyl, heterocyclyl, heterocyclyl-(C 1 -C 6 )-alkyl, phenyl-O—(C 1 -C 6 )-alkyl, heteroaryl-O—(C 1 -C 6 )-alkyl, heterocyclyl-O—(C 1 -C 6 )-alkyl, phenyl-N(R 3 )—(C 1 -C 6 )-alkyl, heteroaryl-N(R 3 )—(C 1 -C 6 )-alkyl, heterocyclyl-N(R 3 )—(C 1 -C 6 )-alkyl, phenyl-S(O) n —(C 1 -C 6 )-alkyl, heteroaryl-S(O) n —(C 1 -C 6 )-alkyl or heterocyclyl-S(O) n —(C 1 -C 6 )-alkyl, where the fifteen latter radicals are each substituted by s radicals selected from the group consisting of nitro, halogen, cyano, thiocyanato, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, R 3 O(O)C, (R 3 ) 2 N(O)C, R 3 O, (R 3 ) 2 N, R 4 (O) n S, R 3 O(O) 2 S, (R 3 ) 2 N(O) 2 S and R 3 O—(C 1 -C 6 )-alkyl, and where heterocyclyl bears n oxo groups,
R 3 is hydrogen, (C 1 -C 6 )-alkyl, halo-(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 4 is (C 1 -C 6 )-alkyl, halo-(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 5 is hydrogen or (C 1 -C 4 )-alkyl,
R 6 is (C 1 -C 4 )-alkyl,
R 7 is acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methyl-benzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylsulfenyl, methylsulfinyl, methylsulfonyl, (C 3 -C 6 )-cycloalkyl, or heteroaryl or heterocyclyl each substituted by s radicals selected from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen,
R 8 is (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyl-O—(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 3 -C 6 )-alkynyl,
R 9 is (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 3 -C 6 )-alkynyl,
R 10 is hydrogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl,
R 11 is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl,
R 1′ is cyano, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, halo-(C 1 -C 6 )-alkyl, OR 8 , SR 8 , or NR 8 R 9 ,
R 2′ 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 )-cycloalkenyl, or (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, where the last six radicals are each substituted by s radicals selected from the group consisting of cyano, halogen, nitro, thiocyanato, OR 10 , S(O) n R 11 , N(R 10 ) 2 , NR 10 OR 10 , COR 10 , OCOR 10 , SCOR 11 , NR 10 COR 10 , NR 10 SO 2 R 11 , CO 2 R 10 , COSR 11 , CON(R 10 ) 2 and (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl; or is 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 10 - heteroaryl, or (C 1 -C 6 )-alkyl-NR 10 -heterocyclyl, where the ten latter radicals are each substituted by s radicals selected from the group consisting of cyano, halogen, nitro, thiocyanato, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, OR 10 , S(O) n R 11 , N(R 10 ) 2 , NR 10 OR 10 , COR 10 , OCOR 10 , SCOR 11 , NR 10 COR 10 , NR 10 SO 2 R 11 , CO 2 R 10 , COSR 11 , CON(R 10 ) 2 and (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl, and where heterocyclyl bears n oxo groups,
R X is (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, or halo-(C 3 -C 6 )-alkynyl, where the six aforementioned radicals are each substituted by s radicals selected from the group consisting of nitro, cyano, (R 6 ) 3 Si, (R 5 O) 2 (O)P, R 2 (O) n S, (R 1 ) 2 N, R 1 O, R 1 (O)C, R 1 O(O)C, R 1 (O)CO, R 2 O(O)CO, R 1 (O)C(R 1 )N, R 2 (O) 2 S(R 1 )N, (C 3 -C 6 )-cycloalkyl, heteroaryl, heterocyclyl and phenyl, where the four latter radicals themselves are in turn substituted by s radicals selected from the group consisting of (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy and halogen, and where heterocyclyl bears n oxo groups; or is (C 3 -C 7 )-cycloalkyl, heteroaryl, heterocyclyl or phenyl, where the four aforementioned radicals are each substituted by s radicals selected from the group consisting of halogen, nitro, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkyl-S(O) n , (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy and (C 1 -C 6 )-alkoxy-(C 1 -C 4 )-alkyl,
R Y is hydrogen, (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 7 )-cycloalkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, (C 2 -C 6 )-alkenyloxy, (C 2 -C 6 )-alkynyloxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfony

Assignees

• Bayer Cropscience Ag

Inventors

• Waldraff Christian
• Braun Ralf
• Dietrich Hansjoerg
• Gatzweiler Elmar
• Rosinger Christopher Hugh

Classifications

• C07D249/14 Primary

  Nitrogen atoms · CPC title

• C07D271/06

  1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles · CPC title

• C07D271/04

  1,2,3-Oxadiazoles; Hydrogenated 1,2,3-oxadiazoles · CPC title

• C07D271/113

  with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical · CPC title

• C07D271/08

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