Pyridazinone herbicides

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

wherein

W is O or S;

R 1 is H, C 1 -C 7 alkyl, C 3 -C 8 alkylcarbonylalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 4 -C 7 alkylcycloalkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 3 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 3 -C 7 alkylthioalkyl, C 1 -C 7 alkoxy or benzyl; or a 5-, or 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon and up to 1 O and 1 S;

R 2 is H, halogen, —CN, —CHO, C 1 -C 7 alkyl, C 3 -C 8 alkylcarbonylalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 7 alkylcarbonyloxy, C 4 -C 7 alkylcycloalkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylamino, C 2 -C 8 dialkylamino, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 3 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy, C 1 -C 5 alkylthio, C 2 -C 3 alkoxycarbonyl; or phenyl optionally substituted by halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

X is O, S or NR 5 ; or

X is —C(R 6 )═C(R 7 )—, wherein the carbon atom bonded to R 6 is also bonded to the carbon atom bonded to R 4 , and the carbon atom bonded to R 7 is also bonded to the phenyl ring moiety in Formula 1;

each R 3 is independently halogen, —CN, nitro, C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl, C 3 -C 5 cycloalkyl, C 4 -C 5 cycloalkylalkyl, C 1 -C 5 haloalkyl, C 3 -C 5 haloalkenyl, C 3 -C 5 haloalkynyl, C 2 -C 5 alkoxyalkyl, C 1 -C 5 alkoxy, C 1 -C 5 haloalkoxy, C 1 -C 5 alkylthio, C 1 -C 5 haloalkylthio or C 2 -C 5 alkoxycarbonyl;

R 4 , R 6 and R 7 are independently H, halogen, nitro, —CN, C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl, C 3 -C 5 cycloalkyl, C 4 -C 5 cycloalkylalkyl, C 1 -C 5 haloalkyl, C 3 -C 5 haloalkenyl, C 3 -C 5 haloalkynyl, C 2 -C 5 alkoxyalkyl, C 1 -C 5 alkoxy, C 1 -C 5 haloalkoxy, C 1 -C 5 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 5 haloalkylthio or C 2 -C 5 alkoxycarbonyl;

R 5 is H, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;

G is G 1 or W 1 G 1 ;

G 1 is H, —C(═O)R 8 , —C(═S)R 8 , —CO 2 R 9 , —C(═O)SR 9 , —S(O) 2 R 8 , —CONR 10 R 11 , —S(O) 2 NR 10 R 11 , or P(═O)(R 12 ) 2 ; or C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, C 2 -C 4 alkoxyalkyl, C 3 -C 6 cycloalkyl or C 4 -C 7 cycloalkylalkyl; or a 5- or 6-membered heterocyclic ring;

W 1 is C 1 -C 4 alkanediyl or C 2 -C 4 alkenediyl;

R 8 and R 10 are independently C 1 -C 7 alkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 3 -C 7 cycloalkyl, C 1 -C 7 haloalkyl, C 3 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 4 -C 7 cycloalkylalkyl; or phenyl, benzyl or a 5- to 6-membered heterocyclic ring, each phenyl, benzyl or heterocyclic ring optionally substituted by halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

R 9 is C 1 -C 7 alkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 3 -C 7 cycloalkyl, C 2 -C 7 haloalkyl, C 3 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 4 -C 7 cycloalkylalkyl; or phenyl, benzyl, or 5- to 6-membered heterocyclic ring, each phenyl, benzyl or heterocyclic ring optionally substituted by halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

R 11 is H, C 1 -C 7 alkyl, C 2 -C 7 alkenyl, C 2 -C 7 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 1 -C 7 haloalkyl or C 2 -C 7 alkoxyalkyl;

R 12 is C 1 -C 7 alkyl or C 1 -C 7 alkoxy; and

n is 0, 1, 2, 3 or 4;

provided that when R 4 is H, then X is —C(R 6 )═C(R 7 )—.

2. A compound of claim 1 wherein

W is O;

X is O, S, —CH═CH—, —C(CH 3 )═CH—, —CH═CF—, —CH═CCl— or —CH═C(CH 3 )—;

R 1 is H, C 1 -C 7 alkyl, C 3 -C 8 alkylcarbonylalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 4 -C 7 alkylcycloalkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 3 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 3 -C 7 alkylthioalkyl, C 1 -C 7 alkoxy or benzyl;

R 2 is H, halogen, —CN, —CHO, C 1 -C 7 alkyl, C 3 -C 8 alkylcarbonylalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 7 alkylcarbonyloxy, C 4 -C 7 alkylcycloalkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylamino, C 2 -C 8 dialkylamino, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 3 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy or C 1 -C 5 alkylthio;

each R 3 is independently halogen, —CN, C 1 -C 3 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylthio or C 1 -C 2 haloalkylthio;

R 4 is halogen, —CN, C 1 -C 3 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylthio or C 1 -C 2 haloalkylthio;

G is G 1 ;

G 1 is H, —C(═O)R 8 , —C(═S)R 8 , —CO 2 R 9 , —C(═O)SR 9 , —S(O) 2 R 8 , —CONR 10 R 11 , —S(O) 2 NR 10 R 11 or P(═O)(R 12 ) 2 ; or C 3 -C 6 cycloalkyl or C 4 -C 7 cycloalkylalkyl;

R 8 and R 10 are independently C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 3 haloalkyl or C 2 -C 7 alkoxyalkyl;

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

R 11 is H, C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 3 haloalkyl or C 2 -C 7 alkoxyalkyl;

R 12 is C 1 -C 3 alkyl or C 1 -C 3 alkoxy; and

n is 0, 1, 2 or 3.

3. A compound of claim 2 wherein

X is —CH═CH—, —C(CH 3 )═CH—, —CH═CF—, —CH═CCl— or —CH═C(CH 3 )—;

R 1 is H, C 1 -C 7 alkyl, C 3 -C 8 alkoxycarbonylalkyl, C 4 -C 7 alkylcycloalkyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 alkoxyalkyl, C 3 -C 7 alkylthioalkyl, C 1 -C 7 alkoxy or benzyl;

R 2 is H, halogen, —CN, —CHO, C 1 -C 7 alkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 7 alkylcarbonyloxy, C 4 -C 7 alkylcycloalkyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylamino, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 alkoxyalkyl or C 1 -C 7 alkoxy;

each R 3 is independently halogen, —CN, C 1 -C 2 alkyl, —CH═CH 2 , —C≡CH, cyclopropyl, C 1 -C 2 haloalkyl or C 1 -C 2 alkoxy;

R 4 is halogen, —CN, C 1 -C 2 alkyl, —CH═CH 2 , —C≡CH, cyclopropyl, C 1 -C 2 haloalkyl or C 1 -C 2 alkoxy;

G 1 is H, —C(═O)R 8 , —CO 2 R 9 , —S(O) 2 R 8 , —CONR 10 R 11 , —S(O) 2 NR 10 R 11 or P(═O)(R 12 ) 2 ;

R 8 , R 9 and R 10 are independently C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl or C 2 -C 7 alkoxyalkyl;

R 11 is H, C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl or C 2 -C 7 alkoxyalkyl; and

R 12 is CH 3 or OCH 3 .

4. A compound of claim 3 wherein

X is —CH═CH—, —CH═CF—, —CH═CCl— or —CH═C(CH 3 )—;

R 1 is methyl, ethyl, n-propyl or 2-methoxyethyl;

R 2 is H, methyl, ethyl, n-propyl, CF 3 or methoxy;

each R 3 is independently halogen, —CN, methyl, ethyl, —CH═CH 2 , —C≡CH, cyclopropyl, CF 3 , methoxy or ethoxy;

R 4 is halogen, —CN, methyl, ethyl, —CH═CH 2 , —C≡CH, cyclopropyl, CF 3 , methoxy or ethoxy;

G 1 is H, —C(═O)R 8 , —CO 2 R 9 , —S(O) 2 R 8 or P(═O)(R 12 ) 2 ;

R 8 and R 9 are independently C 1 -C 7 alkyl or C 2 -C 7 alkoxyalkyl; and

n is 1 or 2.

5. A compound of claim 1 wherein

W is O or S;

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

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

X is O, S or NR 5 ; or

X is —C(R 6 )═C(R 7 )—, wherein the carbon atom bonded to R 6 is also bonded to the carbon atom bonded to R 4 , and the carbon atom bonded to R 7 is also bonded to the phenyl ring moiety in Formula 1;

each R 3 is independently halogen, —CN, C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl, C 3 -C 5 cycloalkyl, C 4 -C 5 cycloalkylalkyl, C 1 -C 5 haloalkyl, C 3 -C 5 haloalkenyl, C 3 -C 5 haloalkynyl, C 2 -C 5 alkoxyalkyl, C 1 -C 5 alkoxy, C 1 -C 5 haloalkoxy, C 1 -C 5 alkylthio, C 1 -C 5 haloalkylthio or C 2 -C 5 alkoxycarbonyl;

R 4 , R 6 and R 7 are independently H, halogen, —CN, C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl, C 3 -C 5 cycloalkyl, C 4 -C 5 cycloalkylalkyl, C 1 -C 5 haloalkyl, C 3 -C 5 haloalkenyl, C 3 -C 5 haloalkynyl, C 2 -C 5 alkoxyalkyl, C 1 -C 5 alkoxy, C 1 -C 5 haloalkoxy, C 1 -C 5 alkylthio, C 1 -C 5 haloalkylthio or C 2 -C 5 alkoxycarbonyl;

R 5 is C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;

G is G 1 ;

G 1 is H, —C(═O)R 8 , —C(═S)R 8 , —CO 2 R 9 , —C(═O)SR 9 , —S(O) 2 R 8 , —CONR 10 R 11 or —S(O) 2 NR 10 R 11 ;

R 8 and R 10 are independently C 1 -C 7 alkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 3 -C 7 cycloalkyl, C 1 -C 7 haloalkyl, C 3 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 4 -C 7 cycloalkylalkyl, phenyl or benzyl;

R 9 is C 1 -C 7 alkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 3 -C 7 cycloalkyl, C 2 -C 7 haloalkyl, C 3 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 4 -C 7 cycloalkylalkyl, phenyl or benzyl;

R 11 is H, C 1 -C 7 alkyl, C 2 -C 7 alkenyl, C 2 -C 7 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 1 -C 7 haloalkyl or C 2 -C 7 alkoxyalkyl; and

n is 0, 1, 2, 3 or 4;

provided that when R 4 is H, then X is —C(R 6 )═C(R 7 )—.

6. A compound of claim 5 wherein

W is O;

X is O, S, —CH═CH—, —C(CH 3 )═CH— or —CH═C(CH 3 )—;

R 1 is C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 3 haloalkyl or C 2 -C 4 alkoxyalkyl;

R 2 is H, halogen, —CN, C 1 -C 4 alkyl, C 3 -C 5 cycloalkyl, C 1 -C 3 haloalkyl, C 2 -C 4 alkoxyalkyl or C 1 -C 3 alkoxy;

each R 3 is independently halogen, —CN, C 1 -C 3 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylthio or C 1 -C 2 haloalkylthio;

R 4 is halogen, —CN, C 1 -C 3 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylthio or C 1 -C 2 haloalkylthio;

G 1 is H, —C(═O)R 8 , —CO 2 R 9 , —S(O) 2 R 8 , —CONR 10 R 11 or —S(O) 2 NR 10 R 11 ;

R 8 and R 10 are independently C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 3 haloalkyl or C 2 -C 7 alkoxyalkyl;

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

R 11 is H, C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 3 haloalkyl or C 2 -C 7 alkoxyalkyl; and

n is 0, 1, 2 or 3.

7. A compound of claim 6 wherein

R 1 is C 1 -C 3 alkyl, allyl, propargyl, CH 2 CH 2 CN, C 1 -C 2 haloalkyl or 2-methoxyethyl;

R 2 is H, halogen, C 1 -C 3 alkyl, cyclopropyl, C 1 -C 2 haloalkyl, methoxy or ethoxy;

each R 3 is independently halogen, —CN, C 1 -C 2 alkyl, —CH═CH 2 , —C≡CH, cyclopropyl, C 1 -C 2 haloalkyl or C 1 -C 2 alkoxy;

R 4 is halogen, —CN, C 1 -C 2 alkyl, —CH═CH 2 , —C═CH, cyclopropyl, C 1 -C 2 haloalkyl or C 1 -C 2 alkoxy;

R 8 , R 9 and R 10 are independently C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl or C 2 -C 7 alkoxyalkyl; and

R 11 is H, C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl or C 2 -C 7 alkoxyalkyl.

8. A compound of claim 7 wherein

R 1 is methyl, ethyl, n-propyl or 2-methoxyethyl;

R 2 is H, methyl, ethyl, n-propyl, CF 3 or methoxy;

each R 3 is independently halogen, —CN, methyl, ethyl, —CH═CH 2 , —C═CH, cyclopropyl, CF 3 , methoxy or ethoxy;

R 4 is halogen, —CN, methyl, ethyl, —CH═CH 2 , —C═CH, cyclopropyl, CF 3 , methoxy or ethoxy;

G 1 is H, —C(═O)R 8 , —CO 2 R 9 or —S(O) 2 R 8 ;

R 8 and R 9 are independently C 1 -C 7 alkyl or C 2 -C 7 alkoxyalkyl; and

n is 1 or 2.

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

4-(2,5-dimethylbenzo[b]thien-3-yl)-5-hydroxy-2,6-dimethyl-3 (2H)-pyridazinone,

5-hydroxy-2,6-dimethyl-4-(2,5,7-trimethylbenzo[b]thien-3-yl)-3 (2H)-pyridazinone,

5-hydroxy-2,6-dimethyl-4-(2,4,6-trimethylbenzo[b]thien-3-yl)-3 (2H)-pyridazinone,

5-hydroxy-2,6-dimethyl-4-(2-methyl-3-benzofuranyl)-3 (2H)-pyridazinone,

5-hydroxy-4-(5-methoxy-3-benzofuranyl)-2,6-dimethyl-3 (2H)-pyridazinone,

4-(5-chloro-2-methyl-3-benzofuranyl)-5-hydroxy-2,6-dimethyl-3 (2H)-pyridazinone,

4-(2,5-dimethyl-3-benzofuranyl)-5-hydroxy-2,6-dimethyl-3 (2H)-pyridazinone,

4-(2,4-dimethyl-3-benzofuranyl)-5-hydroxy-2,6-dimethyl-3 (2H)-pyridazinone,

4-(2,7-dimethyl-3-benzofuranyl)-5-hydroxy-2,6-dimethyl-3 (2H)-pyridazinone,

4-(2-ethyl-5-methyl-3-benzofuranyl)-5-hydroxy-2,6-dimethyl-3 (2H)-pyridazinone,

5-hydroxy-2,6-dimethyl-4-(1-naphthalenyl)-3 (2H)-pyridazinone,

5-hydroxy-2,6-dimethyl-4-(2,5,7-trimethyl-3-benzofuranyl)-3 (2H)-pyridazinone,

4-(5-ethyl-2-methyl-3-benzofuranyl)-5-hydroxy-2,6-dimethyl-3 (2H)-pyridazinone,

5-(acetyloxy)-4-(2,5-dimethyl-3-benzofuranyl)-2,6-dimethyl-3 (2H)-pyridazinone,

5-(acetyloxy)-4-(2,7-dimethyl-3-benzofuranyl)-2,6-dimethyl-3 (2H)-pyridazinone,

5-(acetyloxy)-2,6-dimethyl-4-(2,5,7-trimethyl-3-benzofuranyl)-3 (2H)-pyridazinone,

5-(2,5-dimethyl-3-benzofuranyl)-1,6-dihydro-1,3-dimethyl-6-oxo-4-pyridazinyl 2,2-dimethylpropanoate,

1,6-dihydro-1,3-dimethyl-6-oxo-5-(2,5,7-trimethyl-3-benzofuranyl)-4-pyridazinyl 2,2-dimethylpropanoate, and

4-(2-ethyl-4,6-dimethylbenzo[b]thien-3-yl)-5-hydroxy-2,6-dimethyl-3 (2H)-pyridazinone.

10. A compound of claim 1 selected from a compound of Formula 1 wherein

W is O; R 1 is CH 3 ; R 2 is methyl; X is —CH=CH—; R 4 is OCHF 2 ; G is G 1 ; G 1 is H; and n is 0;

W is O; R 1 is CH 3 ; R 2 is methyl; X is —CH=CH—; R 3 is 5—F; R 4 is Cl; G is G 1 ; G 1 is H; and n is 1;

W is O; R 1 is methyl; R 2 is Cl; X is —CH=CH—; R 4 is methyl; G is G 1 ; G 1 is H; and n is 0;

W is O; R 1 is CH 3 ; R 2 is methyl; X is —CH=CH—; R 4 is Cl; G is G 1 ; G 1 is H; and n is 0;

W is O; R 1 is CH 3 ; R 2 is methyl; X is —CH=CH—; R 3 is 5-methyl; R 4 is OCHF 2 ; G is G 1 ; G 1 is H; and n is 1;

W is O; R 1 is CH 3 ; R 2 is methyl; X is —CH=CH—; R 3 is 5—Br; R 4 is OCHF 2 ; G is G 1 ; G 1 is H; and n is 1;

W is O; R 1 is CH 3 ; R 2 is methyl; X is —CH=CH—; R 3 is 5—Cl; R 4 is Cl; G is G 1 ; G 1 is H; and n is 1; and

W is O; R 1 is methyl; R 2 is methyl; X is —CH=CH—; R 4 is OCHF 2 ; G is G 1 ; G 1 is C(O)Me; and n is 0.

11. 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.

12. 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.

13. 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 and (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, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb, and (b16) herbicide safeners; and salts of compounds of (b1) through (b16).

14. 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 .

15. A herbicidal mixture comprising a compound of claim 1 , and at least one additional active ingredient selected from amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium, cloransulam-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone-sodium, flumetsulam, flupyrsulfuron-methyl, flupyrsulfuron-sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron-methyl (including sodium salt), iofensulfuron (2-iodo-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide), mesosulfuron-methyl, metazosulfuron (3-chloro-4-(5,6-dihydro-5-methyl-1,4,2-dioxazin-3-yl)-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-1-methyl-1H-pyrazole-5-sulfonamide), metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone-sodium, propyrisulfuron (2-chloro-N-[[(4-dimethoxy-2-pyrimidinyl)amino]carbonyl]-6-propylimidazo[1,2-b]pyridazine-3-sulfonamide), prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone, thifensulfuron-methyl, triafamone (N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide), triasulfuron, tribenuron-methyl, trifloxysulfuron (including sodium salt), triflusulfuron-methyl and tritosulfuron.

16. A herbicidal mixture comprising a compound of claim 1 mixed with rimsulfuron, thifensulfuron-methyl, tribenuron, nicosulfuron, metsulfuron-methyl, flupyrsulfuron-methyl, cloransulam-methyl, pyroxsulam or florasulam.

17. A herbicidal mixture comprising a compound of claim 1 mixed with rimsulfuron.

18. A herbicidal mixture comprising a compound of claim 1 mixed with thifensulfuron-methyl.

19. A herbicidal mixture comprising a compound of claim 1 mixed with tribenuron-methyl.

20. A herbicidal mixture comprising a compound of claim 1 mixed with ethametsulfuron-methyl.

21. A herbicidal mixture comprising a compound of claim 1 mixed with nicosulfuron.