IP Library › Granted Patent US 10,750,743

Granted Patent B2

US 10,750,743 · App. 15/771,867 · Granted Aug 25, 2020

Pyridazinone herbicides

Inventors: Thomas Martin Stevenson (Newark, DE); Thomas Paul Selby (Hockessin, DE); Kimberly Katherine Marcus (Media, PA)

Assignee: FMC Corporation

A01N43/58 A01N43/647 A01N43/78 A01N43/80 A01N43/90 A01N47/06 C07D401/04 C07D401/10 C07D403/04 C07D405/04 C07D405/10 C07D409/04 C07D409/10 C07D417/04 C07D495/04

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Quick Facts

Patent No.: US 10,750,743
App. No.: 15/771,867
Granted: Aug 25, 2020
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 , G and W are as defined in the disclosure, and A is selected from and X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , Y 1 , Y 2 , and Y 4 are as defined in the disclosure.

Claims (117)

1. A compound of Formula 1, 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; or a 5- or 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon and up to 1O and 1S;

W is O or S;

A is selected from

G is G 1 or W 1 G 1 ;

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

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

R 2 is H, halogen, —CN, —CHO, C 1 -C 7 alkyl, C 3 -C 8 alkylcarbonylalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 1 -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;

each X 1 is independently N or CR 3 ;

each X 2 is independently N or CR 3 ;

each X 3 is independently N or CR 3 ;

each X 4 , X 5 and X 6 is independently N or CR 4 ;

each X 7 , X 8 , X 9 and X 10 is independently N or CR 5 ;

Y 1 is O, S or NR 6 ;

Y 2 is O, S or NR 6 ;

Y 4 is O, S or NR 6 ;

each R 3 is 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 4 is 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 5 is independently 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 5 haloalkylthio or C 2 -C 5 alkoxycarbonyl;

R 6 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 7 is 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 or 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 8 is 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 or 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 or C 4 -C 7 cycloalkylalkyl; or phenyl, benzyl or a 5- to 6-membered heterocyclic ring, each phenyl, benzyl or heterocycling ring optionally substituted by halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

R 10 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

R 11 is C 1 -C 7 alkyl or C 1 -C 7 alkoxy;

provided

i) when A is A-3 and X 2 is CR 3 , then X 3 is other than CR 3 ;

ii) when A is A-3 and X 3 is CR 3 , then X 2 is other than CR 3 ;

iii) when A is A-4 and Y 4 is O, S or NR 6 , then at least one of X 7 , X 8 , X 9 and X 10 is other than CR 5 ; and

iv) when R 1 is CH 3 ; G is H or C(═O)CH 3 ; and R 2 is Cl or Br; then A-3 is other than 4-quinolinyl(5-Cl) and 4-isoquinolinyl.

2. The compound of claim 1 wherein

W is O;

A is A-1, A-2 or A-3;

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

W 1 is C 1 -C 2 alkanediyl or C 2 -C 3 alkenediyl;

each X 1 is independently CR 3 ;

each R 3 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;

each R 4 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;

each R 5 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;

R 6 is H or C 1 -C 3 alkyl;

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

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

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

R 10 is H, C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 3 haloalkyl or C 2 -C 7 alkoxyalkyl; and

R 11 is C 1 -C 3 alkyl or C 1 -C 3 alkoxy.

3. The compound of claim 2 wherein

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;

A is A-1 or A-2;

G 1 is H, —C(═O)R 7 , —CO 2 R 8 , —CONR 9 R 10 or P(═O)R 11 ; or C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 1 -C 4 alkoxyalkyl, C 3 -C 6 cycloalkyl or C 4 -C 7 cycloalkylalkyl;

W 1 is —CH 2 — or —CH═CH—;

R 2 is H, halogen, —CN, —CHO, C 1 -C 7 alkyl, C 1 -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 X 2 is independently CR 3 ;

each X 5 is independently CR 4 ;

Y 1 is O or S;

Y 2 is O or S;

each R 3 is independently H, halogen, C 1 -C 2 alkyl, cyclopropyl or C 1 -C 2 haloalkyl;

each R 4 is independently H, halogen, C 1 -C 2 alkyl, cyclopropyl or C 1 -C 2 haloalkyl;

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

R 8 is H, C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl or C 2 -C 7 alkoxyalkyl;

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

R 10 is H, C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl or C 2 -C 7 alkoxyalkyl; and

R 11 is CH 3 or OCH 3 .

4. The compound of claim 3 wherein

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

A is selected from

G 1 is H, —C(═O)R 7 , —CO 2 R 8 or P(═O)R 11 ; or C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxyalkyl or C 3 -C 6 cycloalkyl;

W 1 is —CH 2 —;

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 H, halogen, methyl, ethyl or CF 3 ;

each R 4 is independently H, halogen, methyl, ethyl or CF 3 ;

R 7 is C 1 -C 7 alkyl or C 2 -C 7 alkoxyalkyl;

R 8 is C 1 -C 7 alkyl or C 2 -C 7 alkoxyalkyl; and

R 11 is OCH 3 .

5. The compound of claim 4 wherein

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

A is selected from A-1-A and A-1-B;

G is G 1 ;

G 1 is H, —C(═O)R 7 , —CO 2 R 8 ; or C 1 -C 4 alkoxyalkyl or C 3 -C 6 cycloalkyl;

R 2 is H, Cl, Br, I, —CN, methyl or methoxy;

each R 3 is independently H, F, Cl, Br or methyl;

each R 4 is independently H, methyl or ethyl;

R 7 is C 1 -C 3 alkyl or C 2 -C 4 alkoxyalkyl; and

R 8 is C 1 -C 3 alkyl or C 2 -C 4 alkoxyalkyl.

6. The compound of claim 3 wherein

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

A is selected from

G 1 is H, —C(═O)R 7 , —CO 2 R 8 or P(═O)R 11 ; or C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxyalkyl or C 3 -C 6 cycloalkyl;

W 1 is —CH 2 —;

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 H, halogen, methyl, ethyl or CF 3 ;

each R 4 is independently H, halogen, methyl, ethyl or CF 3 ;

R 7 is C 1 -C 7 alkyl or C 2 -C 7 alkoxyalkyl;

R 8 is C 1 -C 7 alkyl or C 2 -C 7 alkoxyalkyl; and

R 11 is OCH 3 .

7. The compound of claim 6 wherein

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

A is A-2-A;

G is G 1 ;

G 1 is H, —C(═O)R 7 , —CO 2 R 8 ; or C 1 -C 4 alkoxyalkyl or C 3 -C 6 cycloalkyl;

R 2 is H, Cl, Br, I, —CN, methyl or methoxy;

each R 3 is independently H, F, Cl, Br or methyl;

each R 4 is independently H, methyl or ethyl;

R 7 is C 1 -C 3 alkyl or C 2 -C 4 alkoxyalkyl; and

R 8 is C 1 -C 3 alkyl or C 2 -C 4 alkoxyalkyl.

8. The compound of claim 6 selected from the group consisting of

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

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

5-hydroxy-2,6-dimethyl-4-(3-methyl-1,2-benzisothiazol-4-yl)-3 (2H)-pyridazinone;

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

1,6-dihydro-1,3-dimethyl-5-(5-methylbenzo[b]thien-4-yl)-6-oxo-4-pyridazinyl ethyl carbonate.

9. 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.

10. 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.

11. 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).

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 .

Assignments (2)

PATENT SECURITY AGREEMENT Recorded Apr 17, 2026

From: FMC CORPORATION

To: CITIBANK, N.A.

Reel/Frame 075403/0891 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 20, 2020

From: STEVENSON, THOMAS MARTIN; SELBY, THOMAS PAUL; MARCUS, KIMBERLY KATHERINE

To: FMC CORPORATION

Reel/Frame 051875/0683 →

Continuity (2)

Provisional Application 62247585 · Oct 28, 2015

Related Publication 20180332851A1 · Nov 22, 2018

Cited By (1)

US 12,435,044