IP Library › Granted Patent US 10,597,388

Granted Patent B2

US 10,597,388 · App. 16/115,958 · Granted Mar 24, 2020

Pyridazinone herbicides

Inventors: Thomas Paul Selby (Hockessin, DE); Nicholas Ryan Deprez (East Windsor, NJ); Thomas Martin Stevenson (Newark, DE); Andrew Edmund Taggi (New Hope, PA); John Robbins DeBergh (Middletown, DE)

Assignee: FMC Corporation

C07D409/04 A01N41/10 A01N43/58 A01N43/70 A01N43/90 A01N47/06 A01N47/18 A01N47/36 A01N57/16 A01N57/24 C07D237/14 C07D237/16 C07D237/18 C07D307/81 C07D333/60 C07D403/04 C07D405/04

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Quick Facts

Patent No.: US 10,597,388
App. No.: 16/115,958
Granted: Mar 24, 2020
Kind: B2

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Abstract

Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, wherein 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; and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , 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 (142)

1. A compound selected from Formula 3, 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 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 3;

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 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;

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;

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

R 30 is alkyl.

2. The compound of claim 1 wherein

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

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;

and

n is 0, 1, 2 or 3.

3. The 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.

4. The 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;

n is 1 or 2; and

R 30 is methyl or ethyl.

5. The compound of claim 1 wherein

R 30 is Me, X is —CH═CH—, R 1 is Me, R 2 is Me, R 4 is Me, and n is 0;

R 30 is Me, X is —CH═CH—, R 1 is Me, R 2 is Me, R 3 is 5-Me, and R 4 is Me;

R 30 is Me, X is —CH═CH—, R 1 is Me, R 2 is Me, R 3 is 4,6-di-Me, and R 4 is Me;

R 30 is Me, X is —CH═CH—, R 1 is Me, R 2 is Me, R 3 is 5,7-di-Me, and R 4 is Me;

R 30 is Me, X is —CH═CH—, R 1 is Me, R 2 is Me, R 4 is Et, n is 0;

R 30 is Me, X is —CH═CH—, R 1 is Me, R 2 is Me, R 3 is 5-Me, and R 4 is Et;

R 30 is Me, X is —CH═CH—, R 1 is Me, R 2 is Me, R 3 is 4,6-di-Me, and R 4 is Et;

R 30 is Me, X is —CH═CH—, R 1 is Me, R 2 is Me, R 3 is 5,7-di-Me, and R 4 is Et;

R 30 is Me, X is —CH═CH—, R 1 is Me, R 2 is Et, R 4 is Me, and n is 0;

R 30 is Me, X is —CH═CH—, R 1 is Me, R 2 is Et, R 3 is 5-Me, and R 4 is Me;

R 30 is Me, X is —CH═CH—, R 1 is Me, R 2 is Et, R 3 is 4,6-di-Me, and R 4 is Me;

R 30 is Me, X is —CH═CH—, R 1 is Me, R 2 is Et, R 3 is 5,7-di-Me, and R 4 is Me;

R 30 is Me, X is —CH═CH—, R 1 is Me, R 2 is Et, R 4 is Et, n is 0;

R 30 is Me, X is —CH═CH—, R 1 is Me, R 2 is Et, R 3 is 5-Me, and R 4 is Et;

R 30 is Me, X is —CH═CH—, R 1 is Me, R 2 is Et, R 3 is 4,6-di-Me, and R 4 is Et; or

R 30 is Me, X is —CH═CH—, R 1 is Me, R 2 is Et, R 3 is 5,7-di-Me, and R 4 is Et.

6. The compound of claim 1 selected from

methyl 2-[2-[2-(2,5-dimethylbenzo[b]thien-3yl)acetyl]-2-methylhydrazinylidene]propanoate;

methyl 2-[2-[2-(2,5-dimethyl-3-benzofuranyl)acetyl]-2-methylhydrazinylidene]propanoate;

and 2,5,7-trimethyl-3-benzofuranacetic acid 2-(2-methoxy-1-methyl-2-oxoethylidene)-1-methylhydrazide.

7. A method for preparing a compound of Formula 1b

wherein

X is O, S or NR 5 ; or

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;

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

n is 0, 1, 2, 3 or 4

comprising cyclizing the compound of Formula 3 in the presence of solvent and base

wherein

X is O, S or NR 5 ; or

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;

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

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

R 30 is alkyl.

8. The method of claim 7 preparing a compound of Formula 1b wherein

R 1 is methyl or ethyl;

R 2 is methyl or ethyl;

X is —C(R 6 )═C(R 7 )—;

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

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

R 6 and R 7 are H or halogen; and

n is 0, 1 or 2

comprising cyclizing the compound of Formula 3 in the presence of solvent and base wherein

R 1 is methyl or ethyl;

R 2 is methyl or ethyl;

X is —C(R 6 )═C(R 7 )—;

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

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

R 6 and R 7 are H or halogen;

n is 0, 1 or 2; and

R 30 is methyl or ethyl.

9. A method for preparing a compound of Formula 3

wherein

X is O, S or NR 5 ; or

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;

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

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

R 30 is alkyl;

comprising reacting a hydrazine ester of Formula 4

wherein

R 30 is alkyl;

with an acid chloride of Formula 5

wherein

X is O, S or NR 5 ; or

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;

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

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

in the presence of solvent and base.

10. The method of claim 9 preparing a compound of Formula 3

wherein

R 1 is methyl or ethyl;

R 2 is methyl or ethyl;

X is —C(R 6 )═C(R 7 )—;

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

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

R 6 and R 7 are H or halogen;

n is 0, 1 or 2; and

R 30 is methyl or ethyl

comprising reacting a hydrazine ester of Formula 4 wherein

R 1 is methyl or ethyl;

R 2 is methyl or ethyl; and

R 30 is methyl or ethyl

with an acid chloride of Formula 5 wherein

X is —C(R 6 )═C(R 7 )—;

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

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

R 6 and R 7 are H or halogen; and

n is 0, 1 or 2

in the presence of solvent and base.

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 10, 2020

From: SELBY, THOMAS PAUL; DEPREZ, NICHOLAS RYAN; STEVENSON, THOMAS MARTIN; TISCIONE, MYLES JOSEPH

To: FMC CORPORATION

Reel/Frame 051768/0786 →

Continuity (5)

Division 15307831

Provisional Application 61985895 · Apr 29, 2014

Provisional Application 62004006 · May 28, 2014

Provisional Application 62071949 · Nov 17, 2014

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