IP Library Granted Patent US 11,498,899
Granted Patent B2
US 11,498,899 · App. 16/471,248 · Granted Nov 15, 2022

Nitrone herbicides

Inventor: Matthew James Campbell (Flemington, NJ)
Assignee: FMC Corporation
C07D207/46A01N25/02A01N25/08A01N43/36C07D207/22
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Quick Facts
Patent No.
US 11,498,899
App. No.
16/471,248
Granted
Nov 15, 2022
Kind
B2
Abstract

Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , J 2 , Q 1 , Q 2 , T and Y are as defined in the disclosure. 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 a compound, N-oxide, salt or composition.

Claims (91)

1. A compound selected from 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 4 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 alkenylene, C 2 -C 10 alkynylene, C 2 -C 10 haloalkenylene, C 2 -C 10 haloalkynylene, C 4 -C 10 cycloalkenylene, C 4 -C 10 halocycloalkenylene, C 2 -C 8 alkylenecarbonyl or C 2 -C 8 alkoxyalkylene;

T is H; or

T is J 1 -A-, wherein the free bond projecting to the right next to A indicates the connecting point of J 1 -A- to Q 1 ; or

T is R 17 ON═CR 17a —, (R 18 ) 2 C═NO—, (R 19 ) 2 NN═CR 17a —, (R 18 ) 2 C═NNR 21 , R 20 N═CR 17a —, (R 18 ) 2 C═N—, R 17 ON═CR 17a C(R 22 ) 2 — or (R 18 ) 2 C═NOC(R 23 ) 2 —, wherein the free bond projecting to the right indicates the connecting point to Q 1 ;

T is R 7 , provided T is bonded to a carbon ring member of Q 1 ; or

T is R 9 , provided T is bonded to a nitrogen ring member of Q 1 ;

A is a saturated, partially unsaturated or fully unsaturated chain containing 1 to 3 atoms selected from up to 3 carbon, up to 1 O, up to 1 S and up to 2 N atoms, the chain optionally substituted with up to 2 substituents independently selected from R 15 on carbon atoms and R 16 on nitrogen atoms;

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 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 7a ; or a 4- to 6-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 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 7a on carbon atom ring members and selected from R 9 on nitrogen atom ring members; or

J 1 is C 4 -C 10 cycloalkylalkoxy, C 4 -C 10 cycloalkylalkyl, C 2 -C 8 alkenyloxy, C 2 -C 8 haloalkenyloxy, C 2 -C 8 alkoxyalkoxy, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkylsulfonylalkyl, 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 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C 2 -C 8 alkoxyalkyl, C 2 -C 8 haloalkoxyalkyl, C 3 -C 8 haloalkoxyalkoxy, C 2 -C 8 haloalkoxyhaloalkyl, C 1 -C 8 haloalkyl, C 3 -C 8 halocycloalkyl, C 2 -C 8 alkylcarbonyloxy or C 2 -C 8 haloalkylcarbonyloxy;

J 2 is (—CR 2 R 3 —) z ;

Y is O, S or NR 12 ;

R 1 is H, hydroxy, amino, 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 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 3 -C 6 alkynyl, C 2 -C 6 cyanoalkyl, C 3 -C 6 cycloalkyl, C 3 -C 8 cycloalkenyl, C 4 -C 8 cycloalkylalkyl, C 2 -C 8 alkoxyalkyl, C 3 -C 8 alkoxyalkoxyalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 haloalkenylalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkylsulfonylalkyl, C 5 -C 10 cycloalkylcarbonylalkyl, 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 —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 R 2 and R 3 , bonded to the same carbon atom, is 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 , together with the carbon atom to which they are both bonded, form a C 3 -C 7 cycloalkyl ring;

each R 2 and R 3 bonded to the same carbon atom is defined independent of any R 2 and R 3 bonded to a different carbon atom;

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 11 on nitrogen atom ring members;

each R 7 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 1 -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, C 4 -C 12 trialkylsilylalkoxy or C 1 -C 6 haloalkylamino; 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

two adjacent R 7 , are taken together with the carbon atoms to which they are bonded to form a C 3 -C 7 cycloalkyl ring;

each R 7a is independently halogen, hydroxy, cyano, nitro, C 1 -C 8 alkyl, C 2 -C 4 alkoxyalkyl, C 3 -C 8 alkoxyalkoxyalkyl, 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 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 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, amino, C 1 -C 8 alkylamino, C 1 -C 6 haloalkylamino, C 3 -C 8 cycloalkylamino, C 2 -C 8 dialkylamino, C 2 -C 8 halodialkylamino, formylamino, C 2 -C 8 alkylcarbonylamino, C 2 -C 8 haloalkylcarbonylamino, C 1 -C 6 alkylsulfonylamino, C 1 -C 6 haloalkylsulfonylamino, —SF 5 , —SCN, C 3 -C 12 trialkylsilyl, C 4 -C 12 trialkylsilylalkyl, C 4 -C 12 trialkylsilylalkoxy; or

two adjacent R 7a , are taken together with the carbon atoms to which they are bonded to form a C 3 -C 7 cycloalkyl ring;

each R 8 is independently H, cyano, C 2 -C 3 alkylcarbonyl or C 2 -C 3 haloalkylcarbonyl;

each R 9 and R 11 are independently cyano, C 1 -C 3 alkyl, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, C 3 -C 6 cycloalkyl, C 2 -C 3 alkoxyalkyl, C 1 -C 3 alkoxy, C 2 -C 3 alkylcarbonyl, C 2 -C 3 alkoxycarbonyl, C 2 -C 3 alkylaminoalkyl or C 3 -C 4 dialkylaminoalkyl;

each 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 1 -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, C 4 -C 12 trialkylsilylalkoxy, C 1 -C 6 haloalkylamino, C 1 -C 8 hydroxalkyl or G 2 ; or

each R 10 is independently R 17 ON═CR 17a —, (R 18 ) 2 C═NO—, (R 19 ) 2 NN═CR 17a —, (R 18 ) 2 C═NNR 21 —, R 20 N═CR 17a —, (R 18 ) 2 C═N—, R 17 ON═CR 17a C(R 22 ) 2 —, (R 18 ) 2 C═NOC(R 23 ) 2 —, R 26 S(═O)═N—, R 26 S(═O) 2 NR 25 —C(═O)—or R 26 (R 25 N═) q S(═O) p —, wherein the free bond projecting to the right of any such substituent indicates the connecting point to Q 2 ; or

two adjacent R 10 , are taken together with the carbon atoms to which they are bonded form a C 3 -C 7 cycloalkyl ring;

each R 12 is independently H, cyano, hydroxy, CHO, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, —(C═O)CH 3 or —(C═O)CF 3 ;

each G 1 is independently phenyl, phenylmethyl (i.e. benzyl), pyridinylmethyl, phenylcarbonyl (i.e. benzoyl), phenylcarbonylalkyl, phenoxy, phenylethynyl, phenylsulfonyl or a 5- or 6-membered heterocyclic ring, each optionally substituted on ring members with up to 5 substituents independently selected from R 13 ;

each G 2 is independently phenyl, phenylmethyl (i.e. benzyl), pyridinylmethyl, phenylcarbonyl (i.e. benzoyl), phenylcarbonylalkyl, phenoxy, phenylethynyl, phenylsulfonyl 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 ;

each R 13 is independently halogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH 2 , —SO 2 NH 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 2 -C 8 alkylcarbonyl, C 2 -C 8 haloalkylcarbonyl, C 2 -C 8 alkoxycarbonyl, C 4 -C 10 cycloalkoxycarbonyl, C 5 -C 12 cycloalkylalkoxycarbonyl, C 2 -C 8 alkylaminocarbonyl, C 3 -C 10 dialkylaminocarbonyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 8 alkylcarbonyloxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 alkylaminosulfonyl, C 2 -C 8 dialkylaminosulfonyl, C 3 -C 10 trialkylsilyl, C 1 -C 6 alkylamino, C 2 -C 8 dialkylamino, C 2 -C 8 alkylcarbonylamino, C 1 -C 6 alkylsulfonylamino, phenyl, pyridinyl or thienyl;

each R 15 is independently halogen, cyano, hydroxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkoxycarbonyl or C 3 -C 6 cycloalkyl;

each R 16 is independently H, 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;

each R 17 is independently H, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 4 -C 8 cycloalkylalkyl, 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 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 17a is independently H, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 4 -C 8 cycloalkylalkyl, 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 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 3 -C 10 trialkylsilyl or G 1 ;

each R 18 is independently H, hydroxy, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 4 -C 8 cycloalkylalkyl, 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 19 is independently H, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 4 -C 8 cycloalkylalkyl, 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 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 20 is independently H, hydroxy, amino, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 4 -C 8 cycloalkylalkyl, 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 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 21 is independently H, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 4 -C 8 cycloalkylalkyl, 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 1 -C 6 alkoxy, C 3 -C 10 trialkylsilyl or G 1 ;

each R 22 is independently H, halogen, cyano, hydroxy, C 1 -C 4 alkyl, C 3 -C 8 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkoxycarbonyl or C 3 -C 6 cycloalkyl;

each R 23 is independently H, C 1 -C 4 alkyl, C 3 -C 8 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkoxycarbonyl or C 3 -C 6 cycloalkyl;

each R 25 is independently H, cyano, C 2 -C 3 alkylcarbonyl or C 2 -C 3 haloalkylcarbonyl;

each R 26 is independently H, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 4 -C 8 cycloalkylalkyl, 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 1 -C 6 alkoxy, C 3 -C 10 trialkylsilyl or G 1 ;

each u and v are independently 0, 1 or 2 in each instance of S(═O) u (═NR 8 ) v , provided that the sum of u and v is 0, 1 or 2;

each p and q are independently 0, 1 or 2 in each instance of R 26 (R 25 N═) q S(═O) p —, provided that the sum of p and q is 0, 1 or 2; and

z is 1, 2 or 3.

2. The compound of claim 1 wherein

each R 7 and R 10 is independently halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, C 1 -C 4 nitroalkyl, C 2 -C 4 nitroalkenyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 haloalkoxyalkyl, C 3 -C 4 cycloalkyl, C 3 -C 4 halocycloalkyl, cyclopropylmethyl, methylcyclopropyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 haloalkenyloxy, C 3 -C 4 alkynyloxy, C 3 -C 4 haloalkynyloxy, C 3 -C 4 cycloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, hydroxy, formyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkylcarbonyloxy, C 1 -C 4 alkylsulfonyloxy, C 1 -C 4 haloalkylsulfonyloxy, amino, C 1 -C 4 alkylamino, C 2 -C 4 dialkylamino, formylamino, C 2 -C 4 alkylcarbonylamino, —SF 5 , —SCN, C 3 -C 4 trialkylsilyl, trimethylsilylmethyl or trimethylsilylmethoxy; and

each R 9 and R 11 is C 1 -C 2 alkyl.

3. The compound of claim 2 wherein

Y is O;

R 1 is CH 3 ; and

T, R 2 , R 3 , R 4 , R 5 and R 6 are each H.

4. The compound of claim 3 wherein

Q 1 is a phenyl ring optionally substituted with 1 to 3 substituents or a benzodioxolane ring substituted with 1 to 3 substituents independently selected from R 7 ; and

Q 2 is a phenyl, pyridinyl or thiophenyl ring substituted with 1 to 3 substituents independently selected from R 10 .

5. The compound of claim 4 wherein

each R 7 is independently halogen, cyano, C 1 -C 2 alkyl, C 1 -C 3 haloalkyl or C 1 -C 3 haloalkoxy; and

each R 10 is independently halogen, cyano, C 1 -C 2 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl or C 1 -C 3 alkylsulfonyl.

6. The compound of claim 5 wherein

Q 1 is a phenyl ring having at least one substituent selected from R 7 at the meta (3-) or the para (4-) position or substituted with at least two substituents independently selected from R 7 wherein one substituent is at the-meta position and at least one other substituent is at a para position; and

Q 2 is a phenyl, 2-pyridinyl, 3-pyridinyl or 3-thiophene ring substituted with 1 to 2 substituents independently selected from R 10 .

7. The compound of claim 6 wherein

each R 7 is independently F, CH 3 or CF 3 ; and

each R 10 is F.

8. The compound of claim 1 selected from the group consisting of a compound of Formula 1 wherein Q 1 is Ph(4-CF 3 ), Q 2 if Ph(2,3-di-F), R 1 is CH 3 , J 2 is CH 2 CH 2 and T, R 4 , R 5 and R 6 are H; a compound of Formula 1 wherein Q 1 is Ph(4-CH 3 ), Q 2 if Ph(2,3-di-F), R 1 is CH 3 , J 2 is CH 2 CH 2 and T, R 4 , R 5 and R 6 are H, and a compound of Formula 1 wherein Q 1 is Ph(4-Cl), Q 2 is Ph(2,3-di-F), R 1 is CH 3 , J 2 is CH 2 CH 2 and T, R 4 , R 5 and R 6 are H.

9. The compound of claim 1 selected from the group consisting of

rel-(2S,3R)-3-(4-chlorophenyl)-N-(2,3-difluorophenyl)-3,4-dihydro-5-methyl-2H-pyrrole-2-carboxamide 1-oxide;

rel-(2S,3R)—N-(2,3-difluorophenyl)-3,4-dihydro-5-methyl-3-[4-(trifluoromethyl)phenyl]-2H-pyrrole-2-carboxamide 1-oxide;

rel-(2S,3R)—N-(2-fluorophenyl)-3,4-dihydro-5-methyl-3-[4-(trifluoromethyl)phenyl]-2H-pyrrole-2-carboxamide 1-oxide;

rel-(2S,3R)—N-(2,3-Difluorophenyl)-3,4-dihydro-5-methyl-3-(4-methylphenyl)-2H-pyrrole-2-carboxamide 1-oxide;

rel-(2S,3R)-3-(2,2-Difluoro-1,3-benzodioxol-5-yl)-N-(2,3-difluorophenyl)-3,4-dihydro-5-methyl-2H-pyrrole-2-carboxamide 1-oxide;

rel-(2S,3R)-3-(4-Difluoromethyl)phenyl)-N-(2,3-difluorophenyl) 3,4-dihydro-5-methyl-2H-pyrrole-2-carboxamide 1-oxide;

(2S,3R)—N-(2,3-Difluorophenyl)-3-[4-fluoro-3-(1,1,2,2-tetrafluoroethyoxy)phenyl]-3,4-dihydro-5-methyl-2H-pyrrole-2-carboxamide 1-oxide;

rel-(2S,3R)—N-(2,6-Difluoro-3-pyridinyl)-3,4-dihydro-5-methyl-3-[4-(trifluoromethyl)phenyl]-2H-pyrrole-2-carboxamide 1-oxide;

rel-(2S,3R)—N-(2,3-Difluorophenyl)-3-[3-fluoro-4-(trifluoromethyl)phenyl]-3,4-dihydro-5-methyl-2H-pyrrole-2-carboxamide 1-oxide;

(2S,3R)-3-(4-chlorophenyl)-N-(2,3-difluorophenyl)-3,4-dihydro-5-methyl-2H-pyrrole-2-carboxamide 1-oxide;

(2S,3R)—N-(2,3-difluorophenyl)-3,4-dihydro-5-methyl-3-[4-(trifluoromethyl)phenyl]-2H-pyrrole-2-carboxamide 1-oxide; and

(2S,3R)—N-(2,3-Difluorophenyl)-3,4-dihydro-5-methyl-3-(4-methylphenyl)-2H-pyrrole-2-carboxamide 1-oxide.

10. A herbicidal composition comprising a compound, N-oxide or salt of claim 1 ; and a surfactant, solid diluent or liquid diluent.

11. The herbicidal composition of claim 10 further comprising an additional active ingredient selected from the group consisting of other herbicides and herbicide safeners.

12. A herbicidal mixture comprising (a) a compound of claim 1 ; and (b) an additional active ingredient selected from (b1) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5) 5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6) photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors, (b10) auxin transport inhibitors, (b11) phytoene desaturase (PDS) inhibitors, (b12) 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (b13) homogentisate solenesyltransererase (HST) inhibitors, (b14) cellulose biosynthesis inhibitors, (b15) other herbicides including mitotic disruptors, organic arsenicals, asulam, bromobutide, cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol, fosamine, fosamine-ammonium, hydantocidin, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb, (b16) herbicide safeners, and salts of compounds of (b1) through (b16).

13. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of claim 1 .

Assignments (2)
PATENT SECURITY AGREEMENT Recorded Apr 17, 2026
From: FMC CORPORATION
To: CITIBANK, N.A.
Reel/Frame 075403/0891 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 4, 2021
From: CAMPBELL, MATTHEW JAMES
To: FMC CORPORATION
Reel/Frame 055498/0246 →