IP Library › Patent Application 18277104

Patent Application

App. No. 18/277,104

HERBICIDAL CYCLIC AMIDES N-SUBSTITUTED WITH A HALOALKYLSULFONYLANILIDE GROUP

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Patent No.: US None
App. No.: 18/277,104

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Abstract

Disclosed are compounds of Formula 1, all stereoisomers, N-oxides, and salts thereof, wherein R 1 through R 8 , R f , Q and G 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.

Claims (224)

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

wherein

R 1 is H, C 1 -C 7 alkyl, halogen, CN, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 2 -C 4 cyanoalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 haloalkenyl, C 3 -C 7 haloalkynyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy, C 1 -C 5 alkylthio, C 2 -C 3 alkoxycarbonyl or C 2 -C 7 haloalkoxyalkyl;

R 2 is H, C 1 -C 7 alkyl, halogen, CN, C 1 -C 7 haloalkyl, C 1 -C 7 alkoxy or C 1 -C 5 alkylthio;

R 3 is H, C 1 -C 7 alkyl, halogen, CN, C 2 -C 6 alkenyl, C 2 -C 7 alkynyl, C 3 -C 7 cycloalkyl, C 2 -C 4 cyanoalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 haloalkenyl, C 3 -C 7 haloalkynyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy, C 1 -C 5 alkylthio, C 2 -C 3 alkoxycarbonyl or C 2 -C 7 haloalkoxyalkyl;

R 4 is H, C(═O)R 14 , —C(═S)R 14 , —CO 2 R 14 , —C(═O)SR 14 , —S(O) 2 R 14 , C(═O)NR 13 R 14 , —S(O) 2 NR 13 R 14 , CH 2 OC(═O)OR 14 , CH 2 OC(═O)NR 13 R 14 or CH 2 OC(═O)R 14 ; or propargyl, allyl or benzyl;

R 5 is H, C 2 -C 6 alkenyl, C 2 -C 7 haloalkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 4 cyanoalkyl, C 1 -C 7 haloalkyl, C 3 -C 7 alkylthioalkyl, C 1 -C 7 haloalkoxy, C 2 -C 7 alkoxyalkyl or C 4 -C 7 alkylcycloalkyl;

R 6 is H, C 1 -C 7 alkyl, halogen, CN, C 1 -C 5 alkylthio, C 2 -C 3 alkoxycarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 4 cyanoalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 3 -C 7 alkylthioalkyl, C 1 -C 7 alkoxy, C 1 -C 7 haloalkoxy, C 2 -C 7 haloalkoxyalkyl or C 4 -C 7 alkylcycloalkyl;

R 7 is H, C 1 -C 7 alkyl, halogen, CN, C 1 -C 5 alkylthio, C 2 -C 3 alkoxycarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 4 cyanoalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 3 -C 7 alkylthioalkyl, C 1 -C 7 alkoxy, C 1 -C 7 haloalkoxy, C 2 -C 7 haloalkoxyalkyl or C 4 -C 7 alkylcycloalkyl;

R 8 is H, C 1 -C 7 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 4 cyanoalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 3 -C 7 alkylthioalkyl, C 1 -C 7 alkoxy, C 1 -C 7 haloalkoxy, C 2 -C 7 alkoxyalkyl or C 4 -C 7 alkylcycloalkyl;

Q is CHR 9 , O or a direct bond;

R 9 is H, C 1 -C 7 alkyl, halogen, CN, C 1 -C 5 alkylthio, C 2 -C 3 alkoxycarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 4 cyanoalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 3 -C 7 alkylthioalkyl, C 1 -C 7 alkoxy, C 1 -C 7 haloalkoxy, C 2 -C 7 alkoxyalkyl, C 2 -C 7 haloalkoxyalkyl or C 4 -C 7 alkylcycloalkyl;

G is OR 10 , SR 10 , SOR 10 or SO 2 R 10 ; or

G and R 5 are taken together to form N—OR 15 ;

R 10 is H, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 3 -C 7 halocycloalkyl, C 4 -C 7 alkylcycloalkyl, C 4 -C 7 cycloalkylalkyl, C 4 -C 7 halocycloalkylalkyl, C 5 -C 7 alkylcycloalkylalkyl, C 1 -C 7 haloalkoxy, C 2 -C 7 alkoxyalkyl, C 2 -C 4 cyanoalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 haloalkenyl, C 3 -C 7 alkylthioalkyl, C 2 -C 4 cyanoalkyl, C 4 -C 7 alkylcycloalkyl, C 1 -C 6 nitroalkyl, C 3 -C 6 alkylcarboalkyl, C 3 -C 6 alkoxycarboalkyl, C 2 -C 7 haloalkoxyalkyl, benzyl or C 3 -C 6 alkylcarboalkoxy; or

R 10 is selected from the group consisting of

R 11 is H, C 1 -C 7 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 7 haloalkyl, C 2 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 3 -C 7 alkylthioalkyl, C 1 -C 7 alkoxy, C 1 -C 7 haloalkoxy, C 2 -C 7 alkoxyalkyl or C 4 -C 7 alkylcycloalkyl;

R 12 is H, C 1 -C 7 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl or C 7 haloalkyl;

each R 13 and R 14 is independently H, C 1 -C 7 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 haloalkenyl, C 2 -C 7 alkylalkoxyalkyl, C 3 -C 7 alkylthioalkyl, C 1 -C 7 alkoxy; C 2 -C 7 alkoxyalkyl, C 4 -C 7 alkylcycloalkyl, Ph or benzyl;

R f is C 1 -C 7 haloalkyl;

G and R 8 can be attached to any ring carbon(s) with available valency, said ring is the cyclic amide ring shown in Formula 1;

each R 11 or R 12 can be attached to any ring carbon(s) with available valency, said ring is illustrated in R 10 -1 through R 10 -16 as above; and

R 15 is H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 4 -C 7 cycloalkylalkyl.

2 . The compound of claim 1 wherein

Q is direct bond;

R 1 is H, C 1 -C 7 alkyl, halogen, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 1 -C 7 haloalkyl;

R 2 is H, C 1 -C 7 alkyl, halogen or CN;

R 3 is H, C 1 -C 7 alkyl, halogen, CN, C 1 -C 7 alkoxy or C 1 -C 7 haloalkyl;

R 4 is H, C(═O)R 14 , —C(═S)R 14 , —CO 2 R 14 , —C(═O)SR 14 , —S(O) 2 R 14 , C(═O)NR 13 R 14 , —S(O) 2 NR 13 R 14 , CH 2 OC(═O)OR 14 , CH 2 OC(═O)NR 13 R 14 or CH 2 OC(═O)R 14 ;

R 5 is H, C 2 -C 6 alkenyl, C 2 -C 7 haloalkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 7 alkoxyalkyl or C 4 -C 7 alkylcycloalkyl;

R 6 is H, C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy or C 1 -C 7 haloalkoxy;

R 7 is H, C 1 -C 7 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 2 -C 4 cyanoalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy or C 1 -C 7 haloalkoxy;

R 8 is H, C 1 -C 7 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 2 -C 4 cyanoalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy or C 1 -C 7 haloalkoxy;

G is OR 10 , SR 10 , SOR 10 or SO 2 R 10 ;

R 10 is H, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 3 -C 7 halocycloalkyl, C 4 -C 7 alkylcycloalkyl, C 4 -C 7 cycloalkylalkyl, C 4 -C 7 halocycloalkylalkyl, C 5 -C 7 alkylcycloalkylalkyl, C 1 -C 7 haloalkoxy, C 2 -C 7 alkoxyalkyl, C 2 -C 4 cyanoalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 haloalkenyl, C 3 -C 7 alkylthioalkyl, C 2 -C 7 haloalkoxyalkyl, benzyl or C 4 -C 7 alkylcycloalkyl;

R 11 is H or C 1 -C 7 alkyl;

R 12 is H or C 1 -C 7 alkyl;

each R 13 and R 14 is independently H, C 1 -C 7 haloalkyl or C 1 -C 7 alkyl; and

R f is C 1 -C 3 haloalkyl.

3 . The compound of claim 2 wherein

R 1 is H, C 1 -C 3 alkyl, halogen or C 3 -C 4 cycloalkyl;

R 2 is H, Me, F, Cl or CN;

R 3 is H, Me, F, Cl, —CN, OMe or CF 3 ;

R 4 is H, SO 2 CF 3 , SO 2 CH 3 , CO 2 Me, COMe, CH 2 OCO-t-Bu, CH 2 OCO-n-Bu, CH 2 OCO-c-hexyl, CH 2 OCO-c-pentyl, CH 2 OCOCH 2 CH 3 , COMe, CH 2 OCOPh, CH 2 OCO-i-Bu, CH 2 OCOMe, CH 2 OCO-sec-Bu, CH 2 OCO-n-Pr and CH 2 OCO-i-Pr or (C═O)SMe;

R 5 is H, C 4 -C 7 cycloalkylalkyl or C 2 -C 7 alkoxyalkyl;

R 6 is H, C 1 -C 7 alkyl or C 1 -C 7 alkoxy;

R 7 is H, C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy or C 1 -C 7 haloalkoxy;

R 8 is H, C 1 -C 7 alkyl or C 1 -C 7 alkoxy;

G is OR 10 or SR 10 ; and

R 10 is C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 3 -C 7 halocycloalkyl, C 4 -C 7 alkylcycloalkyl, C 4 -C 7 cycloalkylalkyl, C 4 -C 7 halocycloalkylalkyl, C 5 -C 7 alkylcycloalkylalkyl, C 2 -C 4 cyanoalkyl, C 3 -C 7 alkylthioalkyl, benzyl or C 4 -C 7 alkylcycloalkyl.

4 . The compound of claim 3 wherein

R 1 is H, Me, halogen or cyclopropyl;

R 2 is H or F;

R 3 is Me or F;

R 4 is H, CH 2 OCOR 14 or —S(O) 2 R 14 ;

R 5 is H;

R 6 is H, Me or OMe;

R 7 is H, Me or OMe;

R 8 is H, Me or OMe;

G is OR 10 ;

R 10 is H, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 4 -C 7 halocycloalkylalkyl or C 4 -C 7 alkylcycloalkyl.

5 . (canceled)

6 . (canceled)

7 . The compound of claim 1 wherein

Q is CHR 9 ;

R 1 is H, C 1 -C 7 alkyl, halogen, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 1 -C 7 haloalkyl;

R 2 is H, C 1 -C 7 alkyl, halogen or CN;

R 3 is H, C 1 -C 7 alkyl, halogen, CN, C 1 -C 7 alkoxy or C 1 -C 7 haloalkyl;

R 5 is H, C 2 -C 6 alkenyl, C 2 -C 7 haloalkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 7 alkoxyalkyl or C 4 -C 7 alkylcycloalkyl;

R 6 is H, C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy or C 1 -C 7 haloalkoxy;

G is OR 10 , SR 10 , SOR 10 or SO 2 R 10 ;

R 9 is H, C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy or C 1 -C 7 haloalkoxy;

R 10 is H, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 3 -C 7 halocycloalkyl, C 4 -C 7 alkylcycloalkyl, C 4 -C 7 cycloalkylalkyl, C 4 -C 7 halocycloalkylalkyl, C 5 -C 7 alkylcycloalkylalkyl, C 1 -C 7 haloalkoxy, C 2 -C 7 alkoxyalkyl, C 2 -C 4 cyanoalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 haloalkenyl, C 3 -C 7 alkylthioalkyl, C 2 -C 7 haloalkoxyalkyl, benzyl or C 4 -C 7 alkylcycloalkyl;

R 11 is H or C 1 -C 7 alkyl;

R 12 is H or C 1 -C 7 alkyl;

each R 13 and R 14 is independently H, C 1 -C 7 haloalkyl or C 1 -C 7 alkyl; and

R f is C 1 -C 3 haloalkyl.

8 . The compound of claim 7 wherein

R 1 is H, C 1 -C 3 alkyl, halogen or C 3 -C 4 cycloalkyl;

R 2 is H, Me, F, Cl or CN;

R 3 is H, Me, F, Cl, —CN, OMe or CF 3 ;

R 5 is H, C 4 -C 7 cycloalkylalkyl or C 2 -C 7 alkoxyalkyl;

R 6 is H, C 1 -C 7 alkyl or C 1 -C 7 alkoxy;

R 7 is H, C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy or C 1 -C 7 haloalkoxy;

R 8 is H, C 1 -C 7 alkyl or C 1 -C 7 alkoxy;

G is OR 10 or SR 10 ;

R 9 is H, C 1 -C 7 alkyl or C 1 -C 7 alkoxy; and

9 . (canceled)

10 . (canceled)

11 . The compound of claim 1 wherein

Q is O;

R 1 is H, C 1 -C 7 alkyl, halogen, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 1 -C 7 haloalkyl;

R 2 is H, C 1 -C 7 alkyl, halogen or CN;

R 3 is H, C 1 -C 7 alkyl, halogen, CN, C 1 -C 7 alkoxy or C 1 -C 7 haloalkyl;

R 5 is H, C 2 -C 6 alkenyl, C 2 -C 7 haloalkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 7 alkoxyalkyl or C 4 -C 7 alkylcycloalkyl;

R 6 is H, C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy or C 1 -C 7 haloalkoxy;

G is OR 10 , SR 10 , SOR 10 or SO 2 R 10 ;

R 10 is H, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 3 -C 7 halocycloalkyl, C 4 -C 7 alkylcycloalkyl, C 4 -C 7 cycloalkylalkyl, C 4 -C 7 halocycloalkylalkyl, C 5 -C 7 alkylcycloalkylalkyl, C 1 -C 7 haloalkoxy, C 2 -C 7 alkoxyalkyl, C 2 -C 4 cyanoalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 haloalkenyl, C 3 -C 7 alkylthioalkyl, C 2 -C 7 haloalkoxyalkyl, benzyl or C 4 -C 7 alkylcycloalkyl;

R 11 is H or C 1 -C 7 alkyl;

R 12 is H or C 1 -C 7 alkyl;

each R 13 and R 14 is independently H, C 1 -C 7 haloalkyl or C 1 -C 7 alkyl; and

R f is C 1 -C 3 haloalkyl.

12 . The compound of claim 11 wherein

R 1 is H, C 1 -C 3 alkyl, halogen or C 3 -C 4 cycloalkyl;

R 2 is H, Me, F, Cl or CN;

R 3 is H, Me, F, Cl, —CN, OMe or CF 3 ;

R 5 is H, C 4 -C 7 cycloalkylalkyl or C 2 -C 7 alkoxyalkyl;

R 6 is H, C 1 -C 7 alkyl or C 1 -C 7 alkoxy;

R 7 is H, C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy or C 1 -C 7 haloalkoxy;

R 8 is H, C 1 -C 7 alkyl or C 1 -C 7 alkoxy;

G is OR 10 or SR 10 ; and

13 . The compound of claim 12 wherein

R 1 is H, Me, halogen or cyclopropyl;

R 2 is H or F;

R 3 is Me or F;

R 4 is H, CH 2 OCOR 14 or —S(O) 2 R 14 ;

R 5 is H;

R 6 is H, Me or OMe;

R 7 is H, Me or OMe;

R 8 is H, Me or OMe;

G is OR 10 ;

R 10 is C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 4 -C 7 halocycloalkylalkyl or C 4 -C 7 alkylcycloalkyl.

14 . (canceled)

15 . (canceled)

16 . The compound of claim 1 wherein

R 1 is H, C 1 -C 7 alkyl, halogen, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 1 -C 7 haloalkyl;

R 2 is H, C 1 -C 7 alkyl, halogen or CN;

R 3 is H, C 1 -C 7 alkyl, halogen, CN, C 1 -C 7 alkoxy or C 1 -C 7 haloalkyl;

R 6 is H, C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy or C 1 -C 7 haloalkoxy;

R 7 is H, C 1 -C 7 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 3 -C 7 alkenylalkyl, C 3 -C 7 alkynylalkyl, C 2 -C 4 cyanoalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy or C 1 -C 7 haloalkoxy;

G and R 5 are taken together to form N—OR 15 ;

R 11 is H or C 1 -C 7 alkyl;

R 12 is H or C 1 -C 7 alkyl;

each R 13 and R 14 is independently H, C 1 -C 7 haloalkyl or C 1 -C 7 alkyl;

R f is C 1 -C 3 haloalkyl; and

R 15 is H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 4 -C 7 cycloalkylalkyl.

17 . The compound of claim 16 wherein

R 1 is H, C 1 -C 3 alkyl, halogen or C 3 -C 4 cycloalkyl;

R 2 is H, Me, F, Cl or CN;

R 3 is H, Me, F, Cl, —CN, OMe or CF 3 ;

R 6 is H, C 1 -C 7 alkyl or C 1 -C 7 alkoxy;

R 7 is H, C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy or C 1 -C 7 haloalkoxy; and

R 8 is H, C 1 -C 7 alkyl or C 1 -C 7 alkoxy.

18 . The compound of claim 17 wherein

R 1 is H, Me, halogen or cyclopropyl;

R 2 is H or F;

R 3 is Me or F;

R 4 is H, CH 2 OCOR 14 or —S(O) 2 R 14 ;

R 6 is H, Me or OMe;

R 7 is H, Me or OMe; and

R 8 is H, Me or OMe.

19 . The compound of claim 18 wherein

R 1 is H, Me, F, Cl, Br or cyclopropyl;

R 4 is H, CH 2 OCO-t-Bu or SO 2 CF 3 ; and

R 8 is H.

20 . (canceled)

21 . The compound of claim 16 wherein Q is direct bond.

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

N-[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-

trifluoromethanesulfonamide (Compound 6);

[[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4-

dimethylphenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate

(Compound 5)

N-[2,4-dimethyl-5-[2-oxo-3-(2-propyn-1-yloxy)-1-pyrrolidinyl]phenyl]-1,1,1-

trifluoromethanesulfonamide (Compound 1);

N-[5-[3-(cyclopropyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-

trifluoromethanesulfonamide (Compound 3);

[[5-[3-(cyclopropyloxy)-2-oxo-1-pyrrolidinyl]-2,4-

dimethylphenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate

(Compound 7);

[[5-[3-(cyclobutyloxy)-2-oxo-1-pyrrolidinyl]-2,4-

dimethylphenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate

(Compound 8);

N-[2,4-dimethyl-5-[2-oxo-3-(2-propen-1-yloxy)-1-pyrrolidinyl]phenyl]-1,1,1-

trifluoromethanesulfonamide (Compound 2); and

N-[5-[3-(cyclobutyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-

trifluoromethanesulfonamide (Compound 4).

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

N-[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-

trifluoromethanesulfonamide (Compound 6);

[[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4-

dimethylphenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate

(Compound 5)

N-[2,4-dimethyl-5-[2-oxo-3-(2-propyn-1-yloxy)-1-pyrrolidinyl]phenyl]-1,1,1-

trifluoromethanesulfonamide (Compound 1);

N-[5-[3-(cyclopropyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-

trifluoromethanesulfonamide (Compound 3);

[5-[3-(cyclopropyloxy)-2-oxo-1-pyrrolidinyl]-2,4-

dimethylphenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate

(Compound 7);

[[5-[3-(cyclobutyloxy)-2-oxo-1-pyrrolidinyl]-2,4-

dimethylphenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate

(Compound 8);

N-[2,4-dimethyl-5-[2-oxo-3-(2-propen-1-yloxy)-1-pyrrolidinyl]phenyl]-1,1,1-

trifluoromethanesulfonamide (Compound 2); and

N-[5-[3-(cyclobutyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-

trifluoromethanesulfonamide (Compound 4).

N-[5-[3-(Ethoxyimino)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-

trifluoromethanesulfonamide (Compound 12)

N-[2,4-Dimethyl-5-[2-oxo-3-[(2-propyn-1-yloxy)imino]-1-pyrrolidinyl]phenyl]-1,1,1-

trifluoromethanesulfonamide (Compound 13)

1,1,1-Trifluoro-N-[5-[3-(methoxyimino)-2-oxo-1-pyrrolidinyl]-2,4-

dimethylphenyl]methanesulfonamide (Compound 9)

24 . A herbicidal composition comprising a compound of claim 1 and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.

25 . A herbicidal composition comprising a compound of claim 1 , at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners, and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.

26 . A herbicidal mixture comprising (a) a compound of claim 1 , and (b) at least one 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 solanesyltransferase (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).

27 . 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 .

28 . The method of claim 29 further comprising contacting the vegetation or its environment with a herbicidally effective amount of at least one additional active ingredient selected from (b1) through (b16) and salts of compounds of (b1) through (b16).

29 . The compound of claim 17 wherein Q is direct bond.

30 . The compound of claim 18 wherein Q is direct bond.

31 . The compound of claim 19 wherein Q is direct bond.

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 Sep 21, 2023

From: SELBY, THOMAS PAUL; ZHANG, WANDI; LEVENS, ALISON MARY

To: FMC CORPORATION

Reel/Frame 064980/0342 →