Substituted cyclic amides and their use as herbicides

Patent metadata

Field	Value
Publication number	US-10654804-B2
Application number	US-201615573598-A
Country	US
Kind code	B2
Filing date	Jun 1, 2016
Priority date	Jun 2, 2015
Publication date	May 19, 2020
Grant date	May 19, 2020

Abstract

Also disclosed are compositions containing the compounds, N-oxides and salts, and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of such a compound, N-oxide, salt or composition.

First claim

We claim:

1. A compound of Formula 1, N-oxides and salts thereof:

wherein
Q 1 is a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R 7 ; or a 4- to 7-membered heterocyclic ring or an 8- to 10-membered bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1 to 5 heteroatoms independently selected from up to 2 O, up to 2 S and up to 5 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O) u (═NR 8 ) v , each ring or ring system optionally substituted with up to 5 substituents independently selected from R 7 on carbon atom ring members and selected from R 9 on nitrogen atom ring members; or
Q 1 is C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 2 -C 10 haloalkenyl, C 2 -C 10 haloalkynyl, C 4 -C 10 cycloalkenyl, C 4 -C 10 halocycloalkenyl, C 2 -C 8 alkylcarbonyl or C 2 -C 8 alkoxyalkyl;
Q 2 is a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R 10 ; or a 4- to 7-membered heterocyclic ring or an 8- to 10-membered bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 5 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O) u (═NR 8 ) v , each ring or ring system optionally substituted with up to 5 substituents independently selected from R 10 on carbon atom ring members and selected from R 11 on nitrogen atom ring members; or
Q 2 is C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 2 -C 10 haloalkenyl, C 2 -C 10 haloalkynyl, C 4 -C 10 cycloalkenyl, C 4 -C 10 halocycloalkenyl, C 2 -C 8 alkylcarbonyl or C 2 -C 8 alkoxyalkyl;
J is —CR 2 R 3 —, —NR 2a — or —O—;
Y 1 and Y 2 are each independently O, S or NR 12 ;
R 1 is cyano, formyl, C 3 -C 8 alkylcarbonylalkyl, —C(C 1 -C 4 alkyl)=N—O(C 1 -C 4 alkyl), —C(O)NH 2 , C 2 -C 6 cyanoalkyl, C 3 -C 6 cycloalkyl, C 4 -C 8 cycloalkenyl; or arylcarbonyl, arylalkenylalkyl, arylcarbonylalkyl or —CPh=N—O(C 1 -C 4 alkyl), each optionally substituted on ring members with up to 5 substituents independently selected from R 13 ; or G 1 ; or W 1 G 1 ;
each G 1 is independently phenyl, or a 5- or 6-membered heterocyclic ring, each optionally substituted on ring members with up to 5 substituents independently selected from R 13 ;
W 1 is C 1 -C 3 alkylene, C 2 -C 4 alkenylene, C 2 -C 4 alkynylene, —(C 1 -C 2 alkylene)C(═O)—, —C(═O)(C 1 -C 2 alkylene)-, —CH 2 O—, —CH 2 NH—, —OCH 2 —, —NCH 2 —, —N—, —O—, —S—, —SO— or —SO 2 — wherein the free bond projecting to the left indicates the connecting point of W 1 to N and the free bond projecting to the right indicates the connecting point of W 1 to G 1 ;
R 2 and R 3 are each independently H, halogen, hydroxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxy; or
R 2 and R 3 are taken together with the carbon atom to which they are bonded to form a C 3 -C 7 cycloalkyl ring;
R 2a is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 alkynyl or C 1 -C 6 alkoxy; or
R 1 and R 2a are taken together as C 3 -C 6 alkylene or —CH 2 OCH 2 —;
R 4 and R 5 are each independently H, halogen, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl or C 1 -C 4 alkyl;
R 6 is H, hydroxy, amino, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 3 -C 6 alkynyl, C 2 -C 8 alkoxyalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkylsulfonylalkyl, C 2 -C 8 alkylcarbonyl, C 2 -C 8 haloalkylcarbonyl, C 4 -C 10 cycloalkylcarbonyl, C 2 -C 8 alkoxycarbonyl, C 2 -C 8 haloalkoxycarbonyl, C 4 -C 10 cycloalkoxycarbonyl, C 2 -C 8 alkylaminocarbonyl, C 3 -C 10 dialkylaminocarbonyl, C 4 -C 10 cycloalkylaminocarbonyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 3 -C 8 cycloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 1 -C 6 alkylaminosulfonyl, C 2 -C 8 dialkylaminosulfonyl or C 3 -C 10 trialkylsilyl or G 1 ; or
R 6 and Q 2 are taken together with the nitrogen atom to which they are both bonded to form an 8- to 10-membered bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O) u (═NR 8 ) v , each ring or ring system optionally substituted with up to 5 substituents independently selected from R 7 on carbon atom ring members and selected from R 9 on nitrogen atom ring members;
each R 7 and R 10 is independently halogen, hydroxy, cyano, nitro, amino, C 1 -C 8 alkyl, C 1 -C 8 cyanoalkyl, C 1 -C 8 cyanoalkoxy, C 1 -C 8 haloalkyl, C 1 -C 8 nitroalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 nitroalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C 2 -C 8 alkoxyalkyl, C 3 -C 8 alkoxyalkoxyalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 haloalkoxyhaloalkoxy, C 3 -C 6 cycloalkyl, cyclopropylmethyl, 1-methylcyclopropyl, 2-methylcyclopropyl, C 4 -C 10 cycloalkylalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 5 -C 12 cycloalkylalkenyl, C 5 -C 12 cycloalkylalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 6 -C 12 cycloalkylcycloalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 haloalkoxyalkoxy, C 2 -C 8 alkoxyalkoxy, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkylsulfonylalkyl, C 2 -C 8 alkylamino, C 2 -C 8 dialkylamino, C 2 -C 8 halodialkylamino, C 2 -C 8 alkylaminoalkyl, C 2 -C 8 haloalkylaminoalkyl, C 4 -C 10 cycloalkylaminoalkyl, C 3 -C 10 dialkylaminoalkyl, —CHO, C 2 -C 8 alkylcarbonyl, C 2 -C 8 haloalkylcarbonyl, C 4 -C 10 cycloalkylcarbonyl, —C(═O)OH, C 2 -C 8 alkoxycarbonyl, C 2 -C 8 haloalkoxycarbonyl, C 4 -C 10 cycloalkoxycarbonyl, C 5 -C 12 cycloalkylalkoxycarbonyl, —C(═O)NH 2 , C 2 -C 8 alkylaminocarbonyl, C 4 -C 10 cycloalkylaminocarbonyl, C 3 -C 10 dialkylaminocarbonyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, C 2 -C 8 alkoxyalkoxy, C 2 -C 8 alkenyloxy, C 2 -C 8 haloalkenyloxy, C 3 -C 8 alkynyloxy, C 3 -C 8 haloalkynyloxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 3 -C 10 alkylcarbonylalkoxy, C 2 -C 8 alkylcarbonyloxy, C 2 -C 8 haloalkylcarbonyloxy, C 4 -C 10 cycloalkylcarbonyloxy, C 1 -C 8 alkylsulfonyloxy, C 1 -C 8 haloalkylsulfonyloxy, C 1 -C 8 alkylthio, C 1 -C 8 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 8 alkylsulfinyl, C 1 -C 8 haloalkylsulfinyl, C 1 -C 8 alkylsulfonyl, C 1 -C 8 haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, formylamino, C 2 -C 8 alkylcarbonylamino, C 2 -C 8 haloalkylcarbonylamino, C 3 -C 8 cycloalkylamino, C 2 -C 8 alkoxycarbonylamino, C 1 -C 6 alkylsulfonylamino, C 1 -C 6 haloalkylsulfonylamino, —SF 5 , —SCN, SO 2 NH 2 , C 3 -C 12 trialkylsilyl, C 4 -C 12 trialkylsilylalkyl or C 4 -C 12 trialkylsilylalkoxy; or G 2 ; or
each R 7 is independently R 26 S(═O)═N—, R 26 S(═O) 2 NR 25 —C(═O)—, R 26 (R 25 N=) q S(═O) p —, wherein the free bond projecting to the right indicates the connecting point to Q 1 ; or
each R 10 is independently R 17 ON═CR 17a —, (R

Assignees

• Fmc Corp

Inventors

• Satterfield Andrew Duncan
• Campbell Matthew James
• Bereznak James Francis
• Whittingham William Guy
• Mitchell Glynn
• Mathews Christopher John
• Scutt James Nicholas
• Morris James Alan
• Dallimore Jonathan Wesley Paul
• Ingram Katharine Mary
• Desson Timothy Robert
• Ling Kenneth

Classifications

• C07D207/277

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• C07D401/12

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

• C07D211/94

  Oxygen atom, e.g. piperidine N-oxide · CPC title

• C07D407/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D409/12

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