Substituted N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide compounds and their use as herbicides

Patent metadata

Field	Value
Publication number	US-9902704-B2
Application number	US-201415027891-A
Country	US
Kind code	B2
Filing date	Oct 7, 2014
Priority date	Oct 10, 2013
Publication date	Feb 27, 2018
Grant date	Feb 27, 2018

Abstract

The present invention relates to a triazole compound of formula I, an N-oxide or an agriculturally suitable salt thereof, wherein the variables are defined as in the specification. The invention further refers to a composition comprising such compound and to the use thereof for controlling unwanted vegetation.

First claim

The invention claimed is:

1. A compound of formula I,

an N-oxide or an agriculturally suitable salt thereof,
wherein
R 1 is selected from the group consisting of halogen, C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, nitro, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, cyano-Z 1 , C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 3 -C 10 -cycloalkyl-Z 1 , C 2 -C 8 -haloalkenyl, C 3 -C 8 -haloalkynyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy-Z 1 , C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkylthio-Z 1 , C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 1 -C 6 -haloalkoxy, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkoxy-Z 1 , R 1b —S(O) k —Z 1 , phenoxy-Z 1 and heterocyclyloxy-Z 1 , where heterocyclyloxy is an oxygen bound 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenoxy and heterocyclyloxy are unsubstituted or substituted by 1, 2, 3 or 4 groups R 11 , which are identical or different;
X is N;
R 2 is selected from the group consisting of hydrogen, halogen, hydroxy-Z 2 , nitro, C 1 -C 4 -nitroalkyl, cyano, C 1 -C 4 -cyanoalkyl, C 1 -C 6 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 3 -C 10 -cycloalkyl-Z 2 , C 3 -C 10 -cycloalkoxy-Z 2 , where the C 3 -C 10 -cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C 1 -C 8 -haloalkyl, C 2 -C 8 -haloalkenyl, C 3 -C 8 -haloalkynyl, C 1 -C 8 -alkoxy-Z 2 , C 1 -C 8 -haloalkoxy-Z 2 , C 3 -C 10 -cycloalkyl-C 1 -C 2 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy-Z 2 , C 1 -C 4 -alkylthio-C 1 -C 4 -alkylthio-Z 2 , C 2 -C 8 -alkenyloxy-Z 2 , C 2 -C 8 -alkynyloxy-Z 2 , C 2 -C 8 -haloalkenyloxy-Z 2 , C 3 -C 8 -haloalkynyloxy-Z 2 , C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkoxy-Z 2 , (tri-C 1 -C 4 -alkyl)silyl-Z 2 , R 2b —S(O) k —Z 2 , R 2c —C(═O)—Z 2 , R 2d O—C(═O)—Z 2 , R 2d O—N═CH—Z 2 , R 2d O—N═CC 1 -C 4 -alkyl-Z 2 , R 2d O—N═CC 1 -C 4 -haloalkyl-Z 2 , R 2c R 2d C═N—O—C 1 -C 4 -alkyl, R 2e R 2f N—C(═O)—Z 2 , R 2g R 2h N—Z 2 , phenyl-Z 2a , heterocyclyl-Z 2a , where heterocyclyl is a 3-, 4-, 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenyl-Z 2a and heterocyclyl-Z 2a are unsubstituted or substituted by 1, 2, 3 or 4 groups R 21 , which are identical or different,
rhodano, C 3 -C 6 -cycloalkenyl, OC(O)OR 22 , OC(O)N(R 22 ) 2 , ONC(R 23 ) 2 , OSO 2 R 25 , SO 2 OR 22 , SO 2 N(R 22 ) 2 , N(R 22 )C(O) OR 22 , N(R 22 )C(O)N(R 22 ) 2 , C(O)N(R 22 )OR 22 , P(O)(O—C 1 -C 4 -alkyl) 2 , C 1 -C 6 -alkyl-OC(O)R 22 , C 1 -C 6 -alkyl-OSO 2 R 25 , C 1 -C 6 -alkyl-SO 2 OR 22 , C 1 -C 6 -alkyl-SO 2 N(R 22 ) 2 , C 1 -C 6 -alkyl-P(O)(O—C 1 -C 4 -alkyl) 2 ,

R 3 is selected from the group consisting of hydrogen, halogen, hydroxy-Z 2 , nitro, C 1 -C 4 -nitroalkyl, cyano, C 1 -C 4 -cyanoalkyl, C 1 -C 6 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 3 -C 10 -cycloalkyl-Z 2 , C 3 -C 10 -cycloalkoxy-Z 2 , where the C 3 -C 10 -cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C 1 -C 8 -haloalkyl, C 2 -C 8 -haloalkenyl, C 3 -C 8 -haloalkynyl , C 1 -C 8 -alkoxy-Z 2 , C 1 -C 8 -haloalkoxy-Z 2 , C 3 -C 10 -cycloalkyl-C 1 -C 2 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy-Z 2 , C 1 -C 4 -alkythio-C 1 -C 4 -alkylthio-Z 2 , C 2 -C 8 -alkenyloxy-Z 2 , C 2 -C 8 -alkynyloxy-Z 2 , C 2 -C 8 -haloalkenyloxy-Z 2 , C 3 -C 8 -haloalkynyloxy-Z 2 , C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkoxy-Z 2 , (tri-C 1 -C 4 -alkyl)silyl-Z 2 , R 2b —S(O) k —Z 2 , R 2c —C(═O)—Z 2 , R 2d O—C(═O)—Z 2 , R 2d O—N═CH—Z 2 , R 2c R 2d C═N—O—C 1 -C 4 -alkyl, R 2e R 2f N—C(═O)—Z 2 , R 2g R 2h N—Z 2 , phenyl-Z 2a , heterocyclyl-Z 2a , where heterocyclyl is a 3-, 4-, 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenyl-Z 2a and heterocyclyl-Z 2a are unsubstituted or substituted by 1, 2, 3 or 4 groups R 21 , which are identical or different,
rhodano, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkenyl, C 3 -C 6 -cycloalkenyl-C 1 -C 6 -alkyl, C 3 -C 6 -halocycloalkenyl-C 1 -C 6 -alkyl, OC(O)R 22 , OC(O)OR 25 , OC(O)N(R 22 ) 2 , OSO 2 R 25 , SO 2 OR 22 , SO 2 N(R 22 ) 2 , SO 2 N(R 22 )C(O)R 22 , SO 2 N(R 22 )C(O)OR 25 , SO 2 N(R 22 )C(O)N(R 22 ) 2 , N(R 22 )C(O)OR 25 , N(R 22 )C(O)N(R 22 ) 2 , N(R 22 )S(O) 2 OR 22 , N(R 22 )S(O) 2 N(R 22 ) 2 , C(O)N(R 22 )OR 22 , C(O)N(R 22 )N(R 22 ) 2 , C(O)N(R 22 )C(O)R 22 , C(O)N(R 22 )C(O)OR 25 , C(O)N(R 22 )C(O)N(R 22 ) 2 , C(O)N(R 22 )SO 2 R 25 , C(O)N(R 22 )SO 2 OR 22 , C(O)N(R 22 )SO 2 N(R 22 ) 2 , P(O)(OH) 2 , P(O)(O—C 1 -C 4 -alkyl) 2 , C 1 -C 6 -alkyl-OC(O)R 22 , C 1 -C 6 -alkyl-OC(O)OR 25 , C 1 -C 6 -alkyl-OC(O)N(R 22 ) 2 , C 1 -C 6 -alkyl-OSO 2 R 25 , C 1 -C 6 -alkyl-SO 2 OR 22 , C 1 -C 6 -alkyl-SO 2 N(R 22 ) 2 , C 1 -C 6 -alkyl-SO 2 N(R 22 )C(O)R 22 , C 1 -C 6 -alkyl-SO 2 N(R 22 )C(O)OR 25 , C 1 -C 6 -alkyl -SO 2 N(R 22 )C(O)N(R 22 ) 2 , C 1 -C 6 -alkyl-N(R 22 )C(O)OR 25 , C 1 -C 6 -alkyl-N(R 22 )C(O)N(R 22 ) 2 , C 1 -C 6 -alkyl-N(R 22 )S(O) 2 OR 22 , C 1 -C 6 -alkyl-N(R 22 )S(O) 2 N(R 22 ) 2 , C 1 -C 6 -alkyl-C(O)N(R 22 )OR 22 , C 1 -C 6 -alkyl-C(O)N(R 22 )N(R 22 ) 2 , C 1 -C 6 -alkyl-C(O)N(R 22 )C(O)R 22 , C 1 -C 6 -alkyl-C(O)N(R 22 )C(O)OR 25 , C 1 -C 6 -alkyl-C(O)N(R 22 )C(O)N(R 22 ) 2 , C 1 -C 6 -alkyl-C(O)N(R 22 )SO 2 R 25 , C 1 -C 6 -alkyl-C(O)N(R 22 )SO 2 OR 22 , C 1 -C 6 -alkyl-C(O)N(R 22 )SO 2 N(R 22 ) 2 , C 1 -C 6 -alkyl-P(O)(OH) 2 and C 1 -C 6 -alkyl-P(O)(O—C 1 -C 4 -alkyl) 2 ;

R 4 is selected from the group consisting of hydrogen, halogen, C 1 -C 8 -alkyl, cyano-Z 1 , nitro, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 4 -alkyl, where the C 3 -C 7 -cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 1 -C 8 -haloalkyl, C 1 -C 3 -alkylamino, C 1 -C 3 -dialkylamino, C 1 -C 3 -alkylamino-S(O) k , C 1 -C 3 -alkylcarbonyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy-Z 1 , C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkylthio-Z 1 , C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 1 -C 6 -haloalkoxy, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkoxy-Z 1 , R 1b —S(O) k —Z 1 , phenoxy-Z 1 and heterocyclyloxy-Z 1 , where heterocyclyloxy is an oxygen bound 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenoxy and heterocyclyloxy are and wherein R 5 is not methyl; or substituted by 1, 2, 3 or 4 groups R 11 , which are identical or different; and wherein R 5 is not methyl;
R 5 is selected from the group consisting of halogen, cyano-Z 1 , nitro, C 1 -C 8 -alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 4 -alkyl, where the C 3 -C 7 -cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 1 -C 8 -haloalkyl, C 1 -C 3 -alkylamino, C 1 -C 3 -dialkylamino, C 1 -C

Assignees

• Basf Se

Inventors

• Calo Frederick
• Kordes Markus
• Kraus Helmut
• Seitz Thomas
• Newton Trevor William
• Kreuz Klaus
• Pasternak Maciej
• Massa Dario

Classifications

• C07D257/06 Primary

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

• A01N43/653

  1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles · CPC title

• A01N43/713

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

• C07D401/12

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

• A01N43/80

  five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2 · CPC title