# US 10,118,917 B2 · Pyridazinone herbicides

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- Number: US 10,118,917 B2
- Document ID: US10118917B2
- Status: Granted
- Kind: B2
- Application number: 15/307,831
- Filed: 2015-04-27
- Published: 2017-02-23
- Granted: 2018-11-06
- Earliest claimed: 2014-04-29
- Applicants: E I Du Pont De Nemours and Company
- Inventors: Thomas Paul Selby; Nicholas Ryan Deprez; Thomas Martin Stevenson; Andrew Edmund Taggi; John Robbins DeBergh
- Web page: https://patentgrep.com/patent/US10118917B2

## CPC

- C07D 409/04: directly linked by a ring-member-to-ring-member bond
- A01N 41/10: Sulfones; Sulfoxides
- A01N 43/58: 1,2-Diazines; Hydrogenated 1,2-diazines
- A01N 43/70: Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A01N 47/06: containing —O—CO—O— groups; Thio analogues thereof
- A01N 47/18: containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
- A01N 47/36: containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
- A01N 57/16: containing heterocyclic radicals
- A01N 57/24: containing heterocyclic radicals
- C07D 237/14: Oxygen atoms
- C07D 237/16: Two oxygen atoms
- C07D 237/18: Sulfur atoms
- C07D 307/78: Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D 307/81: Radicals substituted by nitrogen atoms not forming part of a nitro radical
- C07D 333/52: Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D 333/60: Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## Abstract

Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, wherein X is O, S or NR5; or X is —C(R6)═C(R7)—, wherein the carbon atom bonded to R6 is also bonded to the carbon atom bonded to R4, and the carbon atom bonded to R7 is also bonded to the phenyl ring moiety in Formula 1; and R1, R2, R3, R4, R5, R6, R7, G and W 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

### Claim 1

A compound selected from Formula 1, N-oxides and salts thereof,
wherein
W is O or S;
R1 is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 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;
R2 is H, halogen, —CN, —CHO, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C2-C4 alkylcarbonyl, C2-C7 alkylcarbonyloxy, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, C1-C5 alkylthio, C2-C3 alkoxycarbonyl; or phenyl optionally substituted by halogen, C1-C4 alkyl or C1-C4 haloalkyl;
X is O, S or NR5; or
X is —C(R6)═C(R7)—, wherein the carbon atom bonded to R6 is also bonded to the carbon atom bonded to R4, and the carbon atom bonded to R7 is also bonded to the phenyl ring moiety in Formula 1;
each R3 is independently halogen, —CN, nitro, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl, C4-C5 cycloalkylalkyl, C1-C5 haloalkyl, C3-C5 haloalkenyl, C3-C5 haloalkynyl, C2-C5 alkoxyalkyl, C1-C5 alkoxy, C1-C5 haloalkoxy, C1-C5 alkylthio, C1-C5 haloalkylthio or C2-C5 alkoxycarbonyl;
R4, R6 and R7 are independently H, halogen, nitro, —CN, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl, C4-C5 cycloalkylalkyl, C1-C5 haloalkyl, C3-C5 haloalkenyl, C3-C5 haloalkynyl, C2-C5 alkoxyalkyl, C1-C5 alkoxy, C1-C5 haloalkoxy, C1-C5 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C5 haloalkylthio or C2-C5 alkoxycarbonyl;
R5 is H, C1-C3 alkyl or C1-C3 haloalkyl;
G is G1 or W1G1;
G1 is H, —C(═O)R8, —C(═S)R8, —CO2R9, —C(═O)SR9, —S(O)2R8, —CONR10R11, —S(O)2NR10R11, or P(═O)(R12)2; or C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C2-C4 alkoxyalkyl, C3-C6 cycloalkyl or C4-C7 cycloalkylalkyl; or a 5- or 6-membered heterocyclic ring;
W1 is C1-C4 alkanediyl or C2-C4 alkenediyl;
R8 and R10 are independently C1-C7 alkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C4-C7 cycloalkylalkyl; or phenyl, benzyl or a 5- to 6-membered heterocyclic ring, each phenyl, benzyl or heterocyclic ring optionally substituted by halogen, C1-C4 alkyl or C1-C4 haloalkyl;
R9 is C1-C7 alkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C2-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C4-C7 cycloalkylalkyl; or phenyl, benzyl, or 5- to 6-membered heterocyclic ring, each phenyl, benzyl or heterocyclic ring optionally substituted by halogen, C1-C4 alkyl or C1-C4 haloalkyl;
R11 is H, C1-C7 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C1-C7 haloalkyl or C2-C7 alkoxyalkyl;
R12 is C1-C7 alkyl or C1-C7 alkoxy; and
n is 0, 1, 2, 3 or 4;
provided that when R4 is H, then X is —C(R6)═C(R7)—.

### Claim 2 (depends on 1)

A compound of claim 1 wherein
W is O;
X is O, S, —CH═CH—, —C(CH3)═CH—, —CH═CF—, —CH═CCl— or —CH═C(CH3)—;
R1 is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy or benzyl;
R2 is H, halogen, —CN, —CHO, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C2-C4 alkylcarbonyl, C2-C7 alkylcarbonyloxy, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy or C1-C5 alkylthio;
each R3 is independently halogen, —CN, C1-C3 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C2 haloalkoxy, C1-C2 alkylthio or C1-C2 haloalkylthio;
R4 is halogen, —CN, C1-C3 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C2 haloalkoxy, C1-C2 alkylthio or C1-C2 haloalkylthio;
G is G1;
G1 is H, —C(═O)R8, —C(═S)R8, —CO2R9, —C(═O)SR9, —S(O)2R8, —CONR10R11, —S(O)2NR10R11 or P(═O)(R12)2; or C3-C6 cycloalkyl or C4-C7 cycloalkylalkyl;
R8 and R10 are independently C1-C7 alkyl, C3-C7 cycloalkyl, C1-C3 haloalkyl or C2-C7 alkoxyalkyl;
R9 is C1-C7 alkyl, C3-C7 cycloalkyl, C2-C3 haloalkyl or C2-C7 alkoxyalkyl;
R11 is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C3 haloalkyl or C2-C7 alkoxyalkyl;
R12 is C1-C3 alkyl or C1-C3 alkoxy; and
n is 0, 1, 2 or 3.

### Claim 3 (depends on 2)

A compound of claim 2 wherein
X is —CH═CH—, —C(CH3)═CH—, —CH═CF—, —CH═CCl— or —CH═C(CH3)—;
R1 is H, C1-C7 alkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy or benzyl;
R2 is H, halogen, —CN, —CHO, C1-C7 alkyl, C2-C4 alkylcarbonyl, C2-C7 alkylcarbonyloxy, C4-C7 alkylcycloalkyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl or C1-C7 alkoxy;
each R3 is independently halogen, —CN, C1-C2 alkyl, —CH═CH2, —C≡CH, cyclopropyl, C1-C2 haloalkyl or C1-C2 alkoxy;
R4 is halogen, —CN, C1-C2 alkyl, —CH═CH2, —C≡CH, cyclopropyl, C1-C2 haloalkyl or C1-C2 alkoxy;
G1 is H, —C(═O)R8, —CO2R9, —S(O)2R8, —CONR10R11, —S(O)2NR10R11 or P(═O)(R12)2;
R8, R9 and R10 are independently C1-C7 alkyl, C3-C7 cycloalkyl or C2-C7 alkoxyalkyl;
R11 is H, C1-C7 alkyl, C3-C7 cycloalkyl or C2-C7 alkoxyalkyl; and
R12 is CH3 or OCH3.

### Claim 4 (depends on 3)

A compound of claim 3 wherein
X is —CH═CH—, —CH═CF—, —CH═CCl— or —CH═C(CH3)—;
R1 is methyl, ethyl, n-propyl or 2-methoxyethyl;
R2 is H, methyl, ethyl, n-propyl, CF3 or methoxy;
each R3 is independently halogen, —CN, methyl, ethyl, —CH═CH2, —C≡CH, cyclopropyl, CF3, methoxy or ethoxy;
R4 is halogen, —CN, methyl, ethyl, —CH═CH2, —C≡CH, cyclopropyl, CF3, methoxy or ethoxy;
G1 is H, —C(═O)R8, —CO2R9, —S(O)2R8 or P(═O)(R12)2;
R8 and R9 are independently C1-C7 alkyl or C2-C7 alkoxyalkyl; and
n is 1 or 2.

### Claim 5 (depends on 1)

A compound of claim 1 wherein
W is O or S;
R1 is C1-C7 alkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl or C1-C7 alkoxy;
R2 is H, halogen, —CN, C1-C7 alkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, C1-C5 alkylthio, C2-C3 alkoxycarbonyl or phenyl;
X is O, S or NR5; or
X is —C(R6)═C(R7)—, wherein the carbon atom bonded to R6 is also bonded to the carbon atom bonded to R4, and the carbon atom bonded to R7 is also bonded to the phenyl ring moiety in Formula 1;
each R3 is independently halogen, —CN, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl, C4-C5 cycloalkylalkyl, C1-C5 haloalkyl, C3-C5 haloalkenyl, C3-C5 haloalkynyl, C2-C5 alkoxyalkyl, C1-C5 alkoxy, C1-C5 haloalkoxy, C1-C5 alkylthio, C1-C5 haloalkylthio or C2-C5 alkoxycarbonyl;
R4, R6 and R7 are independently H, halogen, —CN, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl, C4-C5 cycloalkylalkyl, C1-C5 haloalkyl, C3-C5 haloalkenyl, C3-C5 haloalkynyl, C2-C5 alkoxyalkyl, C1-C5 alkoxy, C1-C5 haloalkoxy, C1-C5 alkylthio, C1-C5 haloalkylthio or C2-C5 alkoxycarbonyl;
R5 is C1-C3 alkyl or C1-C3 haloalkyl;
G is G1;
G1 is H, —C(═O)R8, —C(═S)R8, —CO2R9, —C(═O)SR9, —S(O)2R8, —CONR10R11 or —S(O)2NR10R11;
R8 and R10 are independently C1-C7 alkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C4-C7 cycloalkylalkyl, phenyl or benzyl;
R9 is C1-C7 alkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C2-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C4-C7 cycloalkylalkyl, phenyl or benzyl;
R11 is H, C1-C7 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C1-C7 haloalkyl or C2-C7 alkoxyalkyl; and
n is 0, 1, 2, 3 or 4;
provided that when R4 is H, then X is —C(R6)═C(R7)—.

### Claim 6 (depends on 5)

A compound of claim 5 wherein
W is O;
X is O, S, —CH═CH—, —C(CH3)═CH— or —CH═C(CH3)—;
R1 is C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, C3-C4 cycloalkyl, C2-C3 cyanoalkyl, C1-C3 haloalkyl or C2-C4 alkoxyalkyl;
R2 is H, halogen, —CN, C1-C4 alkyl, C3-C5 cycloalkyl, C1-C3 haloalkyl, C2-C4 alkoxyalkyl or C1-C3 alkoxy;
each R3 is independently halogen, —CN, C1-C3 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C2 haloalkoxy, C1-C2 alkylthio or C1-C2 haloalkylthio;
R4 is halogen, —CN, C1-C3 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C2 haloalkoxy, C1-C2 alkylthio or C1-C2 haloalkylthio;
G1 is H, —C(═O)R8, —CO2R9, —S(O)2R8, —CONR10R11 or —S(O)2NR10R11;
R8 and R10 are independently C1-C7 alkyl, C3-C7 cycloalkyl, C1-C3 haloalkyl or C2-C7 alkoxyalkyl;
R9 is C1-C7 alkyl, C3-C7 cycloalkyl, C2-C3 haloalkyl or C2-C7 alkoxyalkyl;
R11 is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C3 haloalkyl or C2-C7 alkoxyalkyl; and
n is 0, 1, 2 or 3.

### Claim 7 (depends on 6)

A compound of claim 6 wherein
R1 is C1-C3 alkyl, allyl, propargyl, CH2CH2CN, C1-C2 haloalkyl or 2-methoxyethyl;
R2 is H, halogen, C1-C3 alkyl, cyclopropyl, C1-C2 haloalkyl, methoxy or ethoxy;
each R3 is independently halogen, —CN, C1-C2 alkyl, —CH═CH2, —C≡CH, cyclopropyl, C1-C2 haloalkyl or C1-C2 alkoxy;
R4 is halogen, —CN, C1-C2 alkyl, —CH═CH2, —C═CH, cyclopropyl, C1-C2 haloalkyl or C1-C2 alkoxy;
R8, R9 and R10 are independently C1-C7 alkyl, C3-C7 cycloalkyl or C2-C7 alkoxyalkyl; and
R11 is H, C1-C7 alkyl, C3-C7 cycloalkyl or C2-C7 alkoxyalkyl.

### Claim 8 (depends on 7)

A compound of claim 7 wherein
R1 is methyl, ethyl, n-propyl or 2-methoxyethyl;
R2 is H, methyl, ethyl, n-propyl, CF3 or methoxy;
each R3 is independently halogen, —CN, methyl, ethyl, —CH═CH2, —C═CH, cyclopropyl, CF3, methoxy or ethoxy;
R4 is halogen, —CN, methyl, ethyl, —CH═CH2, —C═CH, cyclopropyl, CF3, methoxy or ethoxy;
G1 is H, —C(═O)R8, —CO2R9 or —S(O)2R8;
R8 and R9 are independently C1-C7 alkyl or C2-C7 alkoxyalkyl; and
n is 1 or 2.

### Claim 9 (depends on 1)

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.

### Claim 10 (depends on 1)

A compound of claim 1 selected from a compound of Formula 1 wherein
W is O; R1 is CH3; R2 is methyl; X is —CH=CH—; R4 is OCHF2; G is G1; G1 is H; and n is 0;
W is O; R1 is CH3; R2 is methyl; X is —CH=CH—; R3 is 5—F; R4 is Cl; G is G1; G1 is H; and n is 1;
W is O; R1 is methyl; R2 is Cl; X is —CH=CH—; R4 is methyl; G is G1; G1 is H; and n is 0;
W is O; R1 is CH3; R2 is methyl; X is —CH=CH—; R4 is Cl; G is G1; G1 is H; and n is 0;
W is O; R1 is CH3; R2 is methyl; X is —CH=CH—; R3 is 5-methyl; R4 is OCHF2; G is G1; G1 is H; and n is 1;
W is O; R1 is CH3; R2 is methyl; X is —CH=CH—; R3 is 5—Br; R4 is OCHF2; G is G1; G1 is H; and n is 1;
W is O; R1 is CH3; R2 is methyl; X is —CH=CH—; R3 is 5—Cl; R4 is Cl; G is G1; G1 is H; and n is 1; and
W is O; R1 is methyl; R2 is methyl; X is —CH=CH—; R4 is OCHF2; G is G1; G1 is C(O)Me; and n is 0.

### Claim 11 (depends on 1)

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.

### Claim 12 (depends on 1)

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.

### Claim 13 (depends on 1)

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).

### Claim 14 (depends on 1)

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.

### Claim 15 (depends on 1)

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.

### Claim 16 (depends on 1)

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.

### Claim 17 (depends on 1)

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

### Claim 18 (depends on 1)

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

### Claim 19 (depends on 1)

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

### Claim 20 (depends on 1)

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

### Claim 21 (depends on 1)

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