IP Library › Granted Patent US 12692238

Granted Patent B2

US 12692238 · App. 18/267,645 · Granted Jul 28, 2026

Substituted pyridazinone herbicides

Inventors: Stephen Frederick Mccann (Newark, DE); Thomas Paul Selby (Hockessin, DE); Thomas Martin Stevenson (Newark, DE); Alison Mary Levens (Wilmington, DE)

Assignee: FMC CORPORATION

C07D237/16 A01N43/58 A01N47/06 A01P13/02 C07D409/04

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Quick Facts

Patent No.: US 12692238
App. No.: 18/267,645
Granted: Jul 28, 2026
Kind: B2

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Abstract

Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides wherein R 1 , R 2 , R 3 , R 4 , R 14 , and X are as defined in the disclosure, A is selected from and R 12 , R 13 , n, X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , Y and Y 1 are as defined in the disclosure.

Claims (112)

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

wherein

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, benzyl or phenyl, the ring in said benzyl or phenyl group optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy; 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, said ring optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy;

R 2 is H, halogen, cyano, formyl, 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 or C 2 -C 3 alkoxycarbonyl; or phenyl optionally substituted by halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

R 3 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 phenyl, the ring in said benzyl or phenyl group optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy; 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, said ring optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy;

R 4 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, (CH 2 CH 2 O) t R 5 ; or benzyl or phenyl, the ring in said benzyl or phenyl group optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy; 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, said ring optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy;

R 5 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 phenyl, the ring in said benzyl or phenyl group optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy; 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, said ring optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy;

t is an integer from 1 to 10;

X is a direct bond, O, S or NR 6 ;

R 6 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 phenyl, the ring in said benzyl or phenyl group optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy; 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, said ring optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy; or

R 4 and R 6 can be taken together with the nitrogen atom to which they are attached to form a 3 to 7 membered ring, containing carbon atoms and optionally 1 to 3 oxygen, sulfur or nitrogen atoms as ring members, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring member is selected from S, S(O) or S(O) 2 , said ring being optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy;

A is selected from

X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 and X 10 are each independently N or CR 7 ;

provided that no more than 4 of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 and X 10 are N;

X 11 is O, S or NR 9 ; or

X 11 is —C(R 10 )—C(R 11 )—, wherein the carbon atom bonded to R 10 is also bonded to the carbon atom bonded to R 13 , and the carbon atom bonded to R 11 is also bonded to the phenyl ring moiety in Formula 1;

Y is O, S or NR 8 ;

Y 1 is O, S, NR or CR 7a R 7b ;

each R 7 is independently H, halogen, cyano, 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 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 5 haloalkylthio or C 2 -C 5 alkoxycarbonyl;

R 7a is H, 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 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 5 haloalkylthio or C 2 -C 5 alkoxycarbonyl;

R 7b is H, 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 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 5 haloalkylthio or C 2 -C 5 alkoxycarbonyl; or

R 7a and R 7b are taken together as ═O; or R 7a and R 7b are taken together with the carbon atom to which they are bonded to form an optionally substituted 3- to 7-membered carbocyclic ring;

R 8 is H, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;

R 9 is H, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;

R 10 and R 11 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;

each R 12 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 13 is 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 14 is H; and

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

2 . The compound of claim 1 wherein

A is A-11;

R 4 is H, C 1 -C 7 alkyl, C 3 -C 8 alkylcarbonylalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 4 C4-C 7 alkylcycloalkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 3 -C 7 cycloalkyl, —C 1 -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, (CH 2 CH 2 O) t R 5 ; or benzyl or phenyl, the ring in said benzyl or phenyl group optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy;

each R 12 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 13 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.

3 . The compound of claim 2 wherein

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;

R 3 is H, C 1 -C 4 alkyl, C 3 -C 8 alkylcarbonylalkyl, 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 7 haloalkyl, C 2 -C 7 alkoxyalkyl or C 1 -C 7 alkoxy;

R 4 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 or C 1 -C 7 alkoxy;

R 12 is independently halogen, —CN, methyl, ethyl, methoxy or ethoxy; and

R 13 is halogen, —CN, methyl, ethyl, —CH═CH 2 , —C≡CH, cyclopropyl, CF 3 , methoxy or ethoxy.

4 . The compound of claim 3 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;

R 3 is H, C 1 -C 4 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl or C 1 -C 7 alkoxy;

R 4 is H, C 1 -C 4 alkyl, 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 or C 1 -C 7 alkoxy;

each R 12 is independently F, Cl, Br, methyl, ethyl or methoxy; and

n is 0, 1 or 2.

5 . The compound of claim 4 wherein

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

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

R 3 is H or methyl;

R 4 is H, C 1 -C 4 alkyl, C 4 -C 7 cycloalkylalkyl or C 1 -C 7 alkoxy;

X 11 is —C(R 10 )═C(R 11 )—; and

independently, R 10 and R 11 are H, halogen or C 1 -C 2 alkyl.

6 . The compound of claim 5 wherein

R 1 is methyl;

R 2 is Me or Cl;

R 3 is H;

R 4 is H, methyl, ethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methoxy or ethoxy; and

R 10 is H and R 11 is H, or R 10 is H and R 11 is CH 3 , or R 6 is CH 3 and R 7 is H.

7 . The compound of claim 4 wherein

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

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

R 3 is H or methyl;

R 4 is H, C 1 -C 4 alkyl, C 4 -C 7 cycloalkylalkyl, or C 1 -C 7 alkoxy;

X 11 is O.

8 . The compound of claim 4 wherein

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

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

R 3 is H or methyl;

R 4 is H, C 1 -C 4 alkyl, C 4 -C 7 cycloalkylalkyl, or C 1 -C 7 alkoxy;

X 11 is S.

9 . The compound of claim 4 wherein

X is a direct bond or O.

10 . The compound of claim 1 wherein

A is selected from A-1, A-4 and A-6;

11 . The compound of claim 10 wherein

A is A-1;

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, 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 X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 and X 9 is CR 7 ;

each R 7 is independently H, halogen, C 1 -C 3 alkyl, C 3 -C 4 cycloalkyl, C 1 -C 3 haloalkyl or C 1 -C 3 alkoxy;

X is a direct bond or O.

12 . The compound of claim 11 wherein

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, C 1 -C 3 alkyl, cyclopropyl, C 1 -C 2 haloalkyl, methoxy or ethoxy;

R 3 is H, C 1 -C 4 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl or C 1 -C 7 alkoxy;

each R 7 is independently H, halogen, C 1 -C 2 alkyl, cyclopropyl or C 1 -C 2 haloalkyl.

13 . The compound of claim 12 wherein

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

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

each R 7 is independently H, halogen, methyl, ethyl or CF 3 .

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

5-[(acetyloxy)methoxy]-6-chloro-4-(2,7-dimethyl-1-naphthalenyl)-2-methyl-3(2H)-pyridazinone;

5-[(acetyloxy)methoxy]-4-(2-bromo-5-fluorobenzo[b]thien-3-yl)-2,6-dimethyl-3(2H)-pyridazinone;

[[5-(2-fluoro-7-methyl-9-anthracenyl)-1,6-dihydro-1,3-dimethyl-6-oxo-4-pyridazinyl]oxy]methyl methyl carbonate;

5-[(acetyloxy)methoxy]-6-chloro-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2H)-pyridazinone; and

5-[(acetyloxy)methoxy]-4-(2-fluoro-7-methyl-9-anthracenyl)-2,6-dimethyl-3(2H)-pyridazinone.

15 . 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.

16 . 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.

17 . 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).

18 . 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 .