Aryl substituted bicyclic compounds as herbicides

Patent metadata

Field	Value
Publication number	US-10442807-B2
Application number	US-201615565482-A
Country	US
Kind code	B2
Filing date	May 2, 2016
Priority date	May 12, 2015
Publication date	Oct 15, 2019
Grant date	Oct 15, 2019

Abstract

Disclosed are compounds of Formula 1, including all N-oxides, stereoisomers, and salts thereof,

wherein Q 1 , Q 2 , R 1 , R 2 , Y, J and R 7 are as defined in the disclosure.

Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or a composition of the invention.

First claim

What is claimed is:

1. A compound selected from Formula 1, N-oxides, stereoisomers and salts thereof,

wherein
Q 1 is a phenyl or benzyl ring or a naphthalenyl ring, each ring optionally substituted with up to 5 substituents independently selected from R 9 ; or a 5- to 6-membered fully unsaturated heterocyclic ring or an 8- to 10-membered heteroaromatic 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 9 on carbon atom ring members and selected from R 10 on nitrogen atom ring members;
Q 2 is a phenyl ring or a naphthalenyl ring, each ring optionally substituted with up to 5 substituents independently selected from R 11 ; or a 5- to 6-membered fully unsaturated heterocyclic ring or an 8- to 10-membered heteroaromatic 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 11 on carbon atom ring members and selected from R 12 on nitrogen atom ring members;
R 1 and R 2 are each independently H, halogen, hydroxy or C 1 -C 4 alkyl;
Y is O, S or NR 15 ;
A is a saturated, partially unsaturated or fully unsaturated chain containing 2 to 4 atoms selected from up to 4 carbon, up to 1 O, up to 1 S and up to 2 N atoms, wherein up to 2 carbon members are independently selected from C(═O) and C(═S) and the sulfur atom member is selected from S(═O) u (═NR 8 ) v ; the said chain optionally substituted with up to 5 substituents independently selected from R 3 on carbon atoms and R 4 on nitrogen atoms;
each R 3 is independently halogen, cyano, hydroxy, —CO 2 H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkoxy, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkoxycarbonyl, C 3 -C 6 cycloalkyl or C 4 -C 6 cycloalkylalkyl; or
two R 3 are taken together with the carbon atom(s) to which they are bonded to form a C 3 -C 7 cycloalkyl ring;
each R 4 is independently cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkoxycarbonyl or C 3 -C 6 cycloalkyl;
J is —CR 5 R 6 — or —CR 5 R 6 —CR 5a R 6a — wherein the —CR 5 R 6 — moiety is directly connected to N;
R 5 and R 6 are each independently H, halogen, hydroxy, C 1 -C 4 alkyl or C 1 -C 4 alkoxy; or
R 5 and R 6 are taken together with the carbon atom to which they are bonded to form a C 3 -C 7 cycloalkyl ring;
R 5a and R 6a are each independently H, halogen or C 1 -C 4 alkyl; or
R 5a and R 6a are taken together with the carbon atom to which they are bonded to form a C 3 -C 7 cycloalkyl ring;
R 7 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, C 3 -C 10 trialkylsilyl or G 1 ;
each R 8 is independently H, cyano, C 2 -C 3 alkylcarbonyl or C 2 -C 3 haloalkylcarbonyl;
each R 9 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 4 cyanoalkyl, C 1 -C 4 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 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 alkoxyalkyl, C 2 -C 8 haloalkoxyalkyl, C 3 -C 8 haloalkoxyalkoxy, C 1 -C 4 hydroxyalkyl, 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 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 2 -C 8 haloalkoxyhaloalkoxy, 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 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, C 4 -C 12 trialkylsilylalkoxy or G 2 ;
each R 11 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 4 cyanoalkyl, C 1 -C 4 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 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 alkoxyalkyl, C 2 -C 8 haloalkoxyalkyl, C 3 -C 8 haloalkoxyalkoxy, C 1 -C 4 hydroxyalkyl, 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 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

Assignees

• Fmc Corp

Inventors

• Campbell Matthew James
• Stevenson Thomas Martin
• Satterfield Andrew Duncan

Classifications

• C07D207/26

  2-Pyrrolidones · CPC title

• C07D487/04 Primary

  Ortho-condensed systems · CPC title

• A01N43/90

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title

• 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

• C07C205/53 Primary

  the carbon skeleton containing six-membered aromatic rings · CPC title