Herbicidal 3-substituted lactams
This disclosure relates, in part, to compounds of Formula 1 (including all stereoisomers), N-oxides of such compounds, and salts of such compounds and N-oxides: wherein L, Y 1 , R 1 , J, Q 1 , R 7 , Y 2 , R 9 and Q 2 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.
1. A compound selected from Formula 1, N-oxides, and salts thereof
wherein
L is selected from
R A is C 1 -C 7 alkyl, C 1 -C 7 haloalkyl, C 3 -C 9 cycloalkyl, C 3 -C 9 halocycloalkyl, C 1 -C 7 alkoxy, C 1 -C 7 haloalkoxy, C 3 -C 9 cycloalkoxy, C 3 -C 9 halocycloalkoxy, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 1 -C 7 alkylamino, C 1 -C 7 haloalkylamino, C 2 -C 9 dialkylamino, C 2 -C 9 halodialkylamino, C 3 -C 9 cycloalkylamino or C 3 -C 9 halocycloalkylamino, each substituted or unsubstituted with up to 3 substituents independently selected from R 8 or G 1 ; or
R A is G 1 or OG 1 ; or
R A is taken together with R 9 as —C(R I )(R J )C(═O)—;
R B is H, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl or C 1 -C 4 alkyl; or phenyl substituted or unsubstituted with halogen or C 1 -C 4 alkyl;
R C is H, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl or C 1 -C 4 alkyl; or phenyl substituted or unsubstituted with halogen or C 1 -C 4 alkyl;
R D is H, C 1 -C 4 alkyl or C 2 -C 4 alkylcarbonyl;
R E is H, hydroxy, amino, cyano, formyl, —C(O)NH 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 cyanoalkyl, C 3 -C 6 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 2 -C 8 alkoxyalkyl, C 3 -C 8 alkoxyalkoxyalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkenylalkyl, C 2 -C 8 haloalkenylalkyl, C 2 -C 8 alkylcarbonyl, C 2 -C 8 haloalkylcarbonyl, C 4 -C 10 cycloalkylcarbonyl, C 5 -C 10 cycloalkylcarbonylalkyl, 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 or C 2 -C 8 dialkylaminosulfonyl; or G E or W E G E ;
R F is H, formyl, —C(O)NH 2 , 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, —P(═O)(OH) 2 , C 1 -C 6 dialkylphosphoryl, C 1 -C 6 haloalkylphosphoryl, C 3 -C 8 cycloalkylphosphoryl, C 2 -C 8 dialkoxyphosphoryl, C 6 -C 14 dicycloalkoxyphosphoryl, C 8 -C 16 dicycloalkylalkoxyphosphoryl, C 2 -C 12 bis(alkylamino)phosphoryl, C 4 -C 24 bis(dialkylamino)phosphoryl; or G F or W F G F ;
R G is formyl, —C(O)NH 2 , 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, —P(═O)(OH) 2 , C 1 -C 6 dialkylphosphoryl, C 1 -C 6 haloalkylphosphoryl, C 3 -C 8 cycloalkylphosphoryl, C 2 -C 8 dialkoxyphosphoryl, C 6 -C 14 dicycloalkoxyphosphoryl, C 8 -C 16 dicycloalkylalkoxyphosphoryl, C 2 -C 12 bis(alkylamino)phosphoryl, C 4 -C 24 bis(dialkylamino)phosphoryl; or phenyl substituted or unsubstituted with R 16 ; or W G G G ;
R I is H, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl or C 1 -C 4 alkyl; or phenyl substituted or unsubstituted with halogen or C 1 -C 4 alkyl;
R J is H, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl or C 1 -C 4 alkyl; or phenyl substituted or unsubstituted with halogen or C 1 -C 4 alkyl;
Q 1 is a phenyl ring or a naphthalenyl ring system, each ring or ring system substituted or unsubstituted 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 14 ) v , each ring or ring system substituted or unsubstituted with up to 5 substituents independently selected from R 10 on carbon atom ring members and selected from R 12 on nitrogen atom ring members; or
Q 2 is a phenyl ring or a naphthalenyl ring system, each ring or ring system substituted or unsubstituted 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 14 ) v , each ring or ring system substituted or unsubstituted with up to 5 substituents independently selected from R 11 on carbon atom ring members and selected from R 13 on nitrogen atom ring members; or
J is —CR 2 R 3 —, —CR 2 R 3 —CR 4 R 5 —, —NR 6 — or —O—;
Y 1 and Y 2 are each independently O, S or NR 15 ;
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 2 -C 8 alkylcarbonyl, C 2 -C 8 haloalkylcarbonyl, C 4 -C 10 cycloalkylcarbonyl, C 5 -C 10 cycloalkylcarbonylalkyl, 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 —CPh=N—O(C 1 -C 4 alkyl), each substituted or unsubstituted on ring members with up to 5 substituents independently selected from R 13 ; or 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 4 and R 5 are each independently H, halogen, hydroxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxy;
R 6 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 6 are taken together as C 3 -C 6 alkylene or —CH 2 OCH 2 —;
R 7 is H, halogen, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl or C 1 -C 4 alkyl;
each R 8 is independently cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH 2 , —SO 2 NH 2 , 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 or C 1 -C 6 alkylsulfonylamino;
R 9 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 ;
each R 10 and R 11 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 hydroxyalkyl, 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 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 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 R 20 S(═O)═N—, R 20 S(═O) 2 NR 19 —C(═O)— or R 20 (R 19 N═) q S(═O) p —, wherein the free bond projecting to the right indicates the connecting point to Q 1 ; or
each R 12 and R 13 is independently cyano, C 1 -C 3 alkyl, C 1 -C 8 hydroxyalkyl, 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 14 is independently H, cyano, C 2 -C 3 alkylcarbonyl or C 2 -C 3 haloalkylcarbonyl;
each R 15 is independently H, cyano, hydroxy, CHO, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, 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; or a 5- or 6-membered heterocyclic ring, each substituted or unsubstituted on ring members with up to 5 substituents independently selected from R 17 ;
each W E , W F and W G is independently —C(═O)—, —C(═O)O—, —C(═O)NH— or —S(═O) 2 —;
each G E , G F and G G is independently phenyl substituted or unsubstituted with R 16 ; or a 5- or 6-membered heterocyclic ring, each heterocyclic ring substituted or unsubstituted on ring members with up to 5 substituents independently selected from R 16 ;
each G 2 is independently phenyl, phenylmethyl, pyridinylmethyl, phenylcarbonyl, phenoxy, phenylethynyl, phenylsulfonyl or a 5- or 6-membered heterocyclic ring, each substituted or unsubstituted on ring members with up to 5 substituents independently selected from R 18 ;
each R 16 , R 17 and R 18 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 19 is independently H, cyano, C 2 -C 3 alkylcarbonyl or C 2 -C 3 haloalkylcarbonyl;
each R 20 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 or 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 14 ) v , provided that the sum of u and v is 0, 1 or 2; and
each p and q are independently 0, 1 or 2 in each instance of R 20 (R 19 N═) q S(═O) p —, provided that the sum of u and v is 0, 1 or 2 and when p is 0, q is other than 1 or 2.
2. The compound of claim 1 wherein
R A is C 1 -C 7 alkyl, C 1 -C 7 haloalkyl, C 3 -C 9 cycloalkyl, C 1 -C 7 alkoxy or C 1 -C 7 haloalkoxy, C 3 -C 9 cycloalkoxy, each substituted or unsubstituted with up to 2 substituents independently selected from R 8 or G 1 ; or
R A is G 1 ;
R B is H, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl or C 1 -C 4 alkyl;
R C is H, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl or C 1 -C 4 alkyl;
R D is H, C 1 -C 3 alkyl or C 2 -C 3 alkylcarbonyl;
R E is H, hydroxy, amino, cyano, formyl, —C(O)NH 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 cyanoalkyl, C 3 -C 6 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 2 -C 8 alkoxyalkyl, C 3 -C 8 alkoxyalkoxyalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkenylalkyl, C 2 -C 8 haloalkenylalkyl, C 2 -C 8 alkylcarbonyl, C 2 -C 8 haloalkylcarbonyl, C 4 -C 10 cycloalkylcarbonyl, C 5 -C 10 cycloalkylcarbonylalkyl, 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 or C 2 -C 8 dialkylaminosulfonyl;
R F is formyl, —C(O)NH 2 , 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, —P(═O)(OH) 2 , C 1 -C 6 dialkylphosphoryl, C 1 -C 6 haloalkylphosphoryl, C 3 -C 8 cycloalkylphosphoryl, C 2 -C 8 dialkoxyphosphoryl, C 6 -C 14 dicycloalkoxyphosphoryl, C 8 -C 16 dicycloalkylalkoxyphosphoryl, C 2 -C 12 bis(alkylamino)phosphoryl, C 4 -C 24 bis(dialkylamino)phosphoryl; or phenyl substituted or unsubstituted with R 16 ;
R G is formyl, —C(O)NH 2 , 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 or C 1 -C 6 alkylaminosulfonyl;
Q 1 is a phenyl ring or a naphthalenyl ring system, each ring or ring system substituted or unsubstituted with up to 5 substituents independently selected from R 10 ; or a 5- 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 2 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 14 ) v , each ring or ring system substituted or unsubstituted with up to 4 substituents independently selected from R 10 on carbon atom ring members and selected from R 12 on nitrogen atom ring members;
Q 2 is a phenyl ring, each ring substituted or unsubstituted with up to 4 substituents independently selected from R 11 ; or a 5- 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 2 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 14 ) v , each ring or ring system substituted or unsubstituted with up to 4 substituents independently selected from R 11 on carbon atom ring members and selected from R 13 on nitrogen atom ring members;
J is —CR 2 R 3 —, —CR 2 R 3 —CR 4 R 5 — or —NR 6 —;
Y 1 and Y 2 are each independently O or S;
R 1 is H, CHO, C 3 -C 8 alkylcarbonylalkyl, 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 4 -C 8 cycloalkylalkyl, C 2 -C 8 alkoxyalkyl, C 3 -C 8 alkoxyalkoxyalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 alkylthioalkyl, 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 2 -C 8 alkylaminocarbonyl, C 3 -C 10 dialkylaminocarbonyl or C 4 -C 10 cycloalkylaminocarbonyl;
R 2 and R 3 are each independently H or C 1 -C 4 alkyl;
R 4 and R 5 are each independently H, halogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy;
R 6 is H, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
R 7 is H, halogen, C 1 -C 4 alkoxy or C 1 -C 4 alkyl;
each R 8 is independently cyano, nitro, —CHO, 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 or C 2 -C 8 alkylcarbonyloxy;
R 9 is H, C 1 -C 6 alkyl, C 2 -C 8 alkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkylsulfonylalkyl, C 2 -C 8 alkylcarbonyl, C 4 -C 10 cycloalkylcarbonyl, C 2 -C 8 alkoxycarbonyl or C 4 -C 10 cycloalkoxycarbonyl;
each R 10 and R 11 is halogen, nitro, 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 alkoxyalkyl, C 3 -C 8 alkoxyalkoxyalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 haloalkoxyhaloalkoxy, C 4 -C 10 cycloalkylalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 5 -C 12 cycloalkylalkenyl, 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 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 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, C 2 -C 8 alkenyloxy, C 2 -C 8 haloalkenyloxy, 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 alkylsulfonyl, C 1 -C 8 haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl;
each G 1 is independently phenyl; or a 6-membered heterocyclic ring, each substituted or unsubstituted on ring members with up to 4 substituents independently selected from R 17 ;
each R 16 and R 17 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 1 -C 8 hydroxyalkyl, C 2 -C 8 haloalkylcarbonyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 alkylaminoalkyl, C 2 -C 8 alkoxycarbonyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkoxycarbonyl, C 5 -C 12 cycloalkylalkoxycarbonyl, C 2 -C 8 alkylaminocarbonyl, C 3 -C 10 dialkylaminocarbonyl, C 3 -C 8 dialkylaminoalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 8 alkylcarbonyloxy or C 1 -C 6 alkylthio; and
provided the sum of u and v is 2.
3. The compound of claim 2 wherein
L is selected from L-1, L-2 or L-3;
R A is C 1 -C 7 alkyl, C 1 -C 7 haloalkyl, C 1 -C 7 alkoxy or C 1 -C 7 haloalkoxy; each substituted or unsubstituted with up to 2 substituents independently selected from R 8 ; or
R A is G 1 ;
R B is H, —OCH 3 , CF 3 or CH 3 ;
R C is H, C 1 -C 2 alkoxy or C 1 -C 2 alkyl;
R D is H, CH 3 , CH 2 CH 3 or —C(═O)CH 3 CH 2 CH 3 ;
R E is H, hydroxy, amino, cyano, formyl, —C(O)NH 2 , C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 2 -C 8 alkoxyalkyl, C 3 -C 8 alkoxyalkoxyalkyl, C 2 -C 8 alkylcarbonyl, C 4 -C 10 cycloalkylcarbonyl, C 5 -C 10 cycloalkylcarbonylalkyl, C 2 -C 8 alkoxycarbonyl, C 4 -C 10 cycloalkoxycarbonyl, C 1 -C 6 alkylsulfonyl;
R F is C 2 -C 8 alkylcarbonyl, 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 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl or C 1 -C 6 alkylaminosulfonyl; or phenyl substituted or unsubstituted with R 16 ;
R G is formyl, C 2 -C 8 alkylcarbonyl, C 2 -C 8 alkoxycarbonyl, C 4 -C 10 cycloalkoxycarbonyl, C 2 -C 8 alkylaminocarbonyl, C 4 -C 10 cycloalkylaminocarbonyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl or C 1 -C 6 alkylaminosulfonyl;
each R 8 is independently C 2 -C 6 alkenyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy;
J is —CR 2 R 3 — or —CR 2 R 3 —CR 4 R 5 —;
Y 1 and Y 2 are each independently O;
R 1 is H, C 3 -C 8 alkylcarbonylalkyl, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 cyanoalkyl, C 3 -C 6 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 2 -C 8 alkoxyalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 alkylcarbonyl, C 2 -C 8 haloalkylcarbonyl, C 4 -C 10 cycloalkylcarbonyl, C 2 -C 8 alkoxycarbonyl or C 2 -C 8 haloalkoxycarbonyl;
Q 1 is a phenyl ring substituted or unsubstituted with up to 4 substituents independently selected from R 10 ; or a 5- to 6-membered heterocyclic ring, each ring 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, each ring substituted or unsubstituted with up to 4 substituents independently selected from R 10 on carbon atom ring members and selected from R 12 on nitrogen atom ring members;
Q 2 is a phenyl ring, substituted or unsubstituted with up to 4 substituents independently selected from R 11 ; or a 5- 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 2 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 14 ) v , each ring or ring system substituted or unsubstituted with up to 4 substituents independently selected from R 11 on carbon atom ring members and selected from R 13 on nitrogen atom ring members;
R 2 and R 3 are each independently H or CH 3 ;
R 4 and R 5 are each independently H, halogen or C 1 -C 4 alkyl;
R 7 is H, F, Cl or CH 3 ;
R 9 is H, C 1 -C 6 alkyl, C 2 -C 8 alkoxyalkyl, C 2 -C 8 alkylcarbonyl or C 2 -C 8 alkoxycarbonyl;
each R 10 and R 11 is independently halogen, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkoxyalkyl, C 3 -C 8 alkoxyalkoxyalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 6 -C 12 cycloalkylcycloalkyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 haloalkoxyalkoxy, C 2 -C 8 alkoxyalkoxy, C 4 -C 10 cycloalkoxyalkyl, C 2 -C 8 alkylcarbonyl, C 2 -C 8 haloalkylcarbonyl, C 4 -C 10 cycloalkylcarbonyl, C 2 -C 8 alkoxycarbonyl, C 4 -C 10 cycloalkoxycarbonyl, C 5 -C 12 cycloalkylalkoxycarbonyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, C 2 -C 8 haloalkenyloxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 3 -C 10 alkylcarbonylalkoxy or C 2 -C 8 haloalkylcarbonyloxy;
each R 12 and R 13 is independently C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl or C 2 -C 3 alkylcarbonyl;
each R 14 is independently H;
R 15 is H, CH 3 , —(C═O)CH 3 or —(C═O)CF 3 ;
each G 1 is independently phenyl substituted or unsubstituted on ring members with up to 3 substituents independently selected from R 17 ; and
each R 16 and R 17 is independently halogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH 2 , —SO 2 NH 2 , C 1 -C 6 alkyl or C 1 -C 6 haloalkyl.
4. The compound of claim 3 wherein
L is selected from L-1 or L-2;
R A is C 1 -C 7 alkyl or C 1 -C 7 alkoxy; each substituted or unsubstituted with up to 2 substituents independently selected from R 8 ;
R B is H, —OCH 3 or CH 3 ;
R C is H or CH 3 ;
R D is CH 3 or CH 2 CH 3 ;
R E is H, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 2 -C 8 alkoxyalkyl, C 2 -C 8 alkylcarbonyl, C 2 -C 8 alkoxycarbonyl, C 4 -C 10 cycloalkoxycarbonyl, C 1 -C 6 alkylsulfonyl;
each R 8 is independently C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy;
J is —CR 2 R 3 —;
Y 1 and Y 2 are each independently O;
R 1 is H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 cyanoalkyl, C 3 -C 6 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 2 -C 8 alkoxyalkyl, C 2 -C 8 haloalkoxyalkyl or C 2 -C 8 alkoxycarbonyl;
Q 1 is a phenyl ring substituted or unsubstituted with up to 4 substituents independently selected from R 10 ;
Q 2 is a phenyl ring, substituted or unsubstituted with up to 4 substituents independently selected from R 11 ; or a 5- to 6-membered heterocyclic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 4 N atoms, wherein up to 2 carbon ring members are independently selected from C(═O) and C(═S), each ring or ring system substituted or unsubstituted with up to 4 substituents independently selected from R 11 on carbon atom ring members and selected from R 13 on nitrogen atom ring members;
R 2 and R 3 are each independently H;
R 7 is H or CH 3 ;
R 9 is H, C 1 -C 6 alkyl or C 2 -C 8 alkoxycarbonyl;
each R 10 and R 11 is independently halogen, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkoxyalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 2 -C 8 haloalkoxyalkoxy, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy or C 2 -C 8 alkoxyalkoxy; and
each R 12 and R 13 is independently C 1 -C 3 alkyl or C 2 -C 3 alkylcarbonyl.
5. The compound of claim 4 wherein
L is selected from L-1;
R A is C 1 -C 3 alkyl substituted or unsubstituted with up to 2 substituents independently selected from R 8 ;
each R 8 is independently C 1 -C 6 alkoxy;
R 1 is H, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 4 -C 8 cycloalkylalkyl or C 2 -C 8 alkoxyalkyl;
Q 1 is a phenyl ring substituted or unsubstituted with up to 3 substituents independently selected from R 10 ;
Q 2 is a phenyl ring, substituted or unsubstituted with up to 4 substituents independently selected from R 11 ;
R 7 is H;
R 9 is H, CH 3 or —C(═O)CH 3 ; and
each R 10 and R 11 is independently halogen, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 3 -C 8 cycloalkyl, C 1 -C 8 alkoxy or C 1 -C 8 haloalkoxy.
6. The compound of claim 4 wherein
L is selected from L-1;
R A is C 1 -C 3 alkoxy, substituted or unsubstituted with up to 2 substituents independently selected from R 8 ;
each R 8 is independently C 1 -C 6 alkoxy;
R 1 is H, CH 3 , CH 2 CH 3 , cyclopropyl, cyclopropylmethyl or CH 2 OCH 3 ;
Q 1 is a phenyl ring substituted or unsubstituted with up to 2 substituents independently selected from R 10 ;
Q 2 is a phenyl ring, substituted or unsubstituted with up to 3 substituents independently selected from R 11 ;
R 7 is H;
R 9 is H; and
each R 10 and R 11 is independently halogen, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy or C 1 -C 8 haloalkoxy.
7. A compound of claim 1 selected from the group consisting of
(3S,4R)—N-(2,3-difluorophenyl)-3-(hydroxymethyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)-3-pyrrolidinecarboxamide (cis);
(3R,4S)—N-(2,3-difluorophenyl)-3-(hydroxymethyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)-3-pyrrolidinecarboxamide (trans);
(3S,4R)-3-[(acetyloxy)methyl]-N-(2,3-difluorophenyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)-3-pyrrolidinenecarboxamide; and
(3S,4R)-3-acetyl-N-(2,3-difluorophenyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)-3-pyrrolidinecarboxamide.
8. 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.
9. 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.
10. 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 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, and (b16) herbicide safeners; and salts of compounds of (b1) through (b16).
11. 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 .