N-(1,3,4-oxadiazol-2-yl)aryl carboxamide derivatives with herbicidal action

Patent metadata

Field	Value
Publication number	US-10556874-B2
Application number	US-201615738618-A
Country	US
Kind code	B2
Filing date	Jun 29, 2016
Priority date	Jul 3, 2015
Publication date	Feb 11, 2020
Grant date	Feb 11, 2020

Abstract

In this formula (I), V, X and Z represent radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen. A represents an oxadiazole radical. W is CY or N.

First claim

The invention claimed is:

1. An N-(1,3,4-oxadiazol-2-yl)arylcarboxamide derivative of formula (I)

wherein the symbols and indices are each defined as follows:
W is N or CY,
X and Z are each independently hydrogen, nitro, halogen, cyano, formyl, thiocyanato, (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 3 -C 6 )-haloalkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-halocycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-halocycloalkyl-(C 1 -C 6 )-alkyl, COR 1 , OR 1 , OCOR 1 , OSO 2 R 2 , S(O) n R 2 , SO 2 OR 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 , or P(O)(OR 5 ) 2 , or
heteroaryl, heterocyclyl or phenyl, each substituted by s radicals selected from the group consisting of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen,

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 , CO 2 R 1 , OCO 2 R 1 , NR 1 CO 2 R 1 , C(O)N(R 1 ) 2 , NR 1 C(O)N(R 1 ) 2 , OC(O)N(R 1 ) 2 , C(O)N(R 1 )OR 1 , NR 1 SO 2 R 2 , NR 1 COR 1 , OR 1 , OSO 2 R 2 , S(O) n R 2 , SO 2 OR 1 , 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-OSO 2 R 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 5 ) 2 , CH 2 P(O)(OR 5 ) 2 , CH═NOR 1 , (C 1 -C 6 )-alkyl-CH═NOR 1 , or (C 1 -C 6 )-alkyl-O—N═C(R 1 ) 2 , or
(C 1 -C 6 )-alkylphenyl, (C 1 -C 6 )-alkylheteroaryl, (C 1 -C 6 )-alkylheterocyclyl, phenyl, heteroaryl or heterocyclyl, 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, 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 wherein heterocyclyl bears n oxo groups,

or
Y and Z together with the two atoms to which they are bonded form a 5-, 6- or 7-membered, unsaturated, partly saturated or saturated ring which, as well as carbon atoms, in each case has s nitrogen atoms, n oxygen atoms, n sulfur atoms and n S(O), S(O) 2 , C═N—R 8 , C(OR 9 ) 2 , C[—O—(CH 2 ) 2 —O—] or C(O) elements as ring members,
wherein the carbon atoms are substituted in each case by s radicals selected from the group consisting of halogen, cyano, (C 1 -C 6 )-alkyl, (C 2 -C 10 )-alkenyl, (C 2 -C 10 )-alkynyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, phenoxy, halo-(C 1 -C 6 )-alkoxy, (C 3 -C 8 )-cycloalkyl, (C 2 -C 8 )-alkoxyalkyl and phenyl,
wherein the nitrogen atoms are substituted in each case by n radicals selected from the group consisting of (C 1 -C 6 )-alkyl and phenyl,
and in which the aforementioned phenyl radicals are substituted in each case by s radicals selected from the group consisting of cyano, nitro, halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl and (C 1 -C 6 )-alkoxy,

V is hydrogen, nitro, halogen, cyano, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, OR 1 or S(O) n R 2 ,
R 1 is hydrogen, or
(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, each substituted by s radicals selected from the group consisting of cyano, halogen, nitro, thiocyanato, OR 3 , S(O) n R 4 , N(R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , SCOR 4 , NR 3 COR 3 , NR 3 SO 2 R 4 , CO 2 R 3 , COSR 4 , CON(R 3 ) 2 and (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl, and wherein 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, (C 1 -C 6 )-alkyl-NR 3 -heterocyclyl, each substituted by s radicals selected from the group consisting of cyano, halogen, nitro, thiocyanato, OR 3 , S(O) n R 4 , N(R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , SCOR 4 , NR 3 COR 3 , NR 3 SO 2 R 4 , CO 2 R 3 , COSR 4 , CON(R 3 ) 2 and (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl, and wherein heterocyclyl bears n oxo groups,
R 3 is hydrogen, (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 4 is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl,
R 5 is (C 1 -C 4 )-alkyl,
n is 0, 1 or 2,
s is 0, 1, 2 or 3,
A is an A1, A2, or A3 radical

R is (C 1 -C 6 )-alkyl-OC(O)N(R 3 ) 2 or (C 1 -C 6 )-alkyl-OC(O)OR 10 ,
R 6 is hydrogen, or
(C 1 -C 6 )-alkyl, R 1 O—(C 1 -C 6 )-alkyl, CH 2 R 7 , (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, OR 1 , NHR 1 , methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methylcarbonyl, trifluoromethylcarbonyl, dimethylamino, acetylamino, methylsulfenyl, methylsulfinyl, or methylsulfonyl, or
heteroaryl, heterocyclyl, benzyl or phenyl, 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, 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 7 is acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, (C 1 -C 6 )-alkoxy, or (C 3 -C 6 )-cycloalkyl, or
heteroaryl, heterocyclyl or phenyl, each substituted by s radicals 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 )-alkoxy or halo-(C 1 -C 6 )-alkoxy,
R 9 is (C 1 -C 6 )-alkyl or halo-(C 1 -C 6 )-alkyl, and
R 10 is (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl or (C 1 -C 6 )-cycloalkyl.

2. The N-(1,3,4-oxadiazol-2-yl)arylcarboxamide derivative of the formula (I) as claimed in claim 1 , wherein
R 6 is hydrogen, (C 1 -C 6 )-alkyl, R 1 O—(C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, or

Assignees

• Bayer Cropscience Ag

Inventors

• Koehn Arnim
• Waldraff Christian
• Ahrens Hartmut
• Heinemann Ines
• Braun Ralf
• Dietrich Hansjoerg
• Rosinger Christopher Hugh
• Gatzweiler Elmar

Classifications

• C07D417/12

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

• C07D271/113 Primary

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

• A01N47/28

  Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< (isoureas, isothioureas A01N47/42) · CPC title

• A01N43/82

  five-membered rings with three ring hetero atoms · CPC title

• A01N41/06 Primary

  Sulfonic acid amides · CPC title