Granted Patent B2

US 12,435,044 · App. 17/280,611 · Granted Oct 7, 2025

Inventors: Thomas Paul Selby (Hockessin, DE); Thomas Martin Stevenson (Newark, DE); Stephen Frederick McCann (Newark, DE); Eric Allen Marshall (Rising Sun, MD); Yuzhong Chen (Wilmington, DE)

Assignee: FMC Corporation

C07D237/16A01N43/58C07D237/14

Abstract

Claims (98)

1. A compound of Formula I and N-oxides or salts thereof,

wherein

R 1 is C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl;

R 2 is Cl;

R 3 is Cl or OR 4 ;

R 4 is H or C 1 -C 4 alkyl;

R 5 is F, Cl or CH 3 ; and

R 6 is H.

2. The compound of claim 1 wherein

R 2 is Cl;

R 3 is OR 4 ;

R 4 is H or methyl; and

R 5 is F, Cl or CH 3 ;

R 6 is H.

3. The compound of any one of claims 1 to 2 wherein R 5 is CH 3 .

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

6-chloro-4-(2,7-dimethyl-1-naphthalenyl)-5-hydroxy-2-methyl-3 (2H)-pyridazinone;

6-chloro-4-(7-fluoro-2-methyl-1-naphthalenyl)-5-hydroxy-2-methyl-3 (2H)-pyridazinone; and

6-chloro-4-(7-chloro-2-methyl-1-naphthalenyl)-5-hydroxy-2-methyl-3 (2H)-pyridazinone.

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

6. 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.

7. A herbicidal mixture comprising (a) a compound of claim 1 , and (b) at least one additional active ingredient.

8. The herbicidal mixture of claim 7 wherein the (b) at least one additional active ingredient is selected from the group consisting of 5-chloro-2-[3-chloro-2-[3-(difluoromethyl)-5-isoxazolyl]phenoxy]-pyrimidine, 1-[2-chloro-6-[(5-chloro-2-pyrimidinyl)oxy]phenyl]-4,4,4-trifluoro-1-butanone, 2,4-D, Acetochlor, Acifluorfen, Atrazine, Carfentrazone, Chlorimuron, Clethodim, Clomazone, Clopyralid, Cloransulam-methyl, Dicamba, Diflufenican, Dimethenamid, Diquat, Flumioxazin, Fluroxypyr, Fluthiacet-methyl, Fomesafen, Glufosinate, Glyphosate, Imazethapyr, Isoxaflutole, Lactofen, Mesotrione, Metribuzin, Pyroxasulfone, Rimsulfuron, Saflufenacil, S-metolachlor, Sulfentrazone, Tembotrione, Thiencarbazone, Tolpyralate, Topramezone, benoxacor, isoxadifen-ethyl, cloquintocet-mexyl and Mefenpyr-diethyl.

9. The herbicidal mixture of claim 8 wherein the (b) at least one additional active ingredient is selected from the group consisting of 5-chloro-2-[3-chloro-2-[3-(difluoromethyl)-5-isoxazolyl]phenoxy]-pyrimidine, atrazine, glyphosate, saflufenacil, pyroxasulfone, 1-[2-chloro-6-[(5-chloro-2-pyrimidinyl)oxy]phenyl]-4,4,4-trifluoro-1-butanone, metribuzin, and rimsulfuron.

10. A herbicidal mixture of claim 8 wherein the (b) at least one additional active ingredient is selected from the group consisting of benoxacor, isoxadifen-ethyl, cloquintocet-mexyl and Mefenpyr-diethyl.

11. A herbicidal mixture of claim 8 wherein the (b) at least one additional active ingredient is selected from the group consisting of S-metolachlor, Sulfentrazone, Clomazone, Chlorimuron, Fomesafen, Flumioxazin, Fluroxypyr, 2,4-D, Isoxaflutole, Diflufenican, Mesotrione, Topramezone, Tolpyralate, Dicamba, Carfentrazone, Clopyralid, Acetochlor and Thiencarbazone.

12. 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 .

13. A process for preparing a compound of Formula I-A,

wherein

R 1 is C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl;

R 2 is Cl;

R 5 is F, Cl or CH 3 ; and

R 6 is H;

the process comprising:

(1) reacting a compound of Formula II

wherein

R 5 is F, Cl or CH 3 ; and

R 6 is H;

with magnesium to form an intermediate compound of Formula III

and

(2) reacting the intermediate compound or Formula III formed in (1) with a compound of Formula IV-B

wherein

R 1 is C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl;

G is C 1 -C 4 alkyl, SO 2 CF 3 or SO 2 (4-Me-Ph).

14. A process for preparing a compound of Formula I-C

wherein

R 1 is C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl;

R 2 is Cl;

R 5 is F, Cl or CH 3 ; and

R 6 is H;

the process comprising:

(1) reacting a compound of Formula I-B,

wherein

R 1 is C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl;

R 5 is F, Cl or CH 3 ; and

R 6 is H;

with a tmp-zinc base, to form a zincated intermediate compound of Formula V

and

(2) reacting the zincated intermediate compound of Formula V formed in (1) with a halogenating agent.

15. A process for preparing a compound of Formula I-D

wherein

R 1 is C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl;

R 2 is Cl;

R 5 is F, Cl or CH 3 ; and

R 6 is H;

the process comprising reacting a compound of Formula I-C,

wherein

R 1 is C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl;

R 2 is Cl;

R 5 is F, Cl or CH 3 ; and

R 6 is H;

with a demethylating agent.

16. A process for preparing a compound of Formula I-E

wherein

R 1 is C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl;

R 5 is F, Cl or CH 3 ; and

R 6 is H;

the process comprising reacting a compound of Formula VI

wherein

R 1 is C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl;

R 5 is F, Cl or CH 3 ; and

R 6 is H;

with phosphorous oxychloride.

17. A process for preparing a compound of Formula I-E

wherein

R 1 is C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl;

R 5 is F, Cl or CH 3 ; and

R 6 is H;

the process comprising:

(1) reacting a compound of Formula II

wherein

R 5 is F, Cl or CH 3 ; and

R 6 is H;

with magnesium to form an intermediate compound of Formula III

and

(2) reacting the intermediate compound or Formula III formed in (1) with a compound of Formula 7

wherein

R 1 is C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl.

Assignments (2)

Continuity (2)

References Cited (28)