IP Library › Granted Patent US 11,213,030
Granted Patent B2
US 11,213,030 · App. 16/623,628 · Granted Jan 4, 2022

4-(3,4-dihydronaphth-1-yl or 2H-chromen-4-yl)-5-hydroxy-2H-pyradizin-3-ones as herbicides

Inventors: Eric Allen Marshall (Rising Sun, MD); John Robbins Debergh (Middletown, DE)
Assignee: FMC Corporation
A01N43/58C07D237/16C07D405/04
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Quick Facts
Patent No.
US 11,213,030
App. No.
16/623,628
Granted
Jan 4, 2022
Kind
B2
Abstract

Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, Formula (1) wherein W, R 1 , R 2 , R 3 , n, R 4 , R 5 , R 6 , L and G 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 (77)

1. A compound selected from Formula 1, N-oxides and salts thereof,

wherein

W is C(R 7 )(R 8 );

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 2 -C 7 alkenyl, C 3 -C 7 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 5 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 3 -C 7 alkylthioalkyl or C 1 -C 7 alkoxy;

R 2 is H, halogen, cyano, —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 2 -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 5 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy, C 1 -C 5 alkylthio or C 2 -C 3 alkoxycarbonyl;

each R 3 is independently H, halogen, nitro, cyano, 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 2 -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 4 haloalkylthio or C 2 -C 5 alkoxycarbonyl;

n is 0 to 3;

each R 4 is independently H, halogen, nitro, cyano, 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 2 -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 4 haloalkylthio or C 2 -C 5 alkoxycarbonyl;

R 5 is H or C 1 -C 5 alkyl;

R 6 is H or C 1 -C 5 alkyl;

R 7 is H or C 1 -C 5 alkyl;

R 8 is H or C 1 -C 5 alkyl;

L is a direct bond, C 1 -C 4 alkanediyl or C 2 -C 4 alkenediyl;

G is H, C(═O)R 9 , C(═S)R 9 , CO 2 R 10 , C(═O)SR 10 , S(O) 2 R 9 , C(═O)N(R 11 )(R 12 ), S(═O) 2 N(R 11 )(R 12 ) or P(═O)(R 13 )(R 14 ), or C 1 -C 7 alkyl, C 2 -C 5 alkenyl, C 2 -C 4 alkynyl, C 1 -C 7 haloalkyl, C 2 -C 5 haloalkenyl, C 2 -C 4 haloalkynyl, C 2 -C 4 alkoxyalkyl, C 3 -C 6 cycloalkyl or C 4 -C 7 cycloalkylalkyl; or a 5- or 6-membered heterocyclic ring optionally substituted by halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

R 9 and R 11 are independently H, 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 10 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 heterocyclic ring optionally substituted by halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

R 12 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 13 is C 1 -C 7 alkyl or C 1 -C 7 alkoxy; and

R 14 is C 1 -C 7 alkyl or C 1 -C 7 alkoxy.

2. The compound of claim 1 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 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl or C 1 -C 7 alkoxy;

R 2 is H, halogen, cyano, —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 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy, C 1 -C 5 alkylthio or C 2 -C 3 alkoxycarbonyl;

each R 3 is independently H, halogen, C 1 -C 5 alkyl, C 3 -C 5 cycloalkyl, C 1 -C 5 haloalkyl, C 1 -C 5 alkoxy or C 1 -C 5 haloalkoxy;

n is 0 to 2;

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

L is a direct bond or C 1 -C 2 alkanediyl;

G is H, C(═O)R 9 , C(═S)R 9 , CO 2 R 10 , C(═O)SR 10 , CON(R 11 )(R 12 ) or P(═O)(R 13 )(R 14 ); 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 2 -C 4 alkoxyalkyl, C 3 -C 6 cycloalkyl or C 4 -C 7 cycloalkylalkyl;

R 9 and R 11 are independently H, C 1 -C 7 alkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 3 -C 7 cycloalkyl or C 1 -C 7 haloalkyl; or phenyl, benzyl, or a 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 10 is C 1 -C 7 alkyl, C 3 -C 7 alkenyl, C 3 -C 7 cycloalkyl, C 2 -C 7 haloalkyl or C 3 -C 7 haloalkenyl; or phenyl, benzyl or a 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 12 is H, C 1 -C 7 alkyl, C 2 -C 7 alkenyl, C 2 -C 7 alkynyl or C 3 -C 7 cycloalkyl;

R 13 is C 1 -C 4 alkyl or C 1 -C 4 alkoxy; and

R 14 is C 1 -C 4 alkyl or C 1 -C 4 alkoxy.

3. The compound of claim 2 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 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 7 alkoxyalkyl or C 1 -C 7 alkoxy;

R 2 is H, halogen, cyano, —CHO, C 1 -C 7 alkyl, C 4 -C 7 alkylcycloalkyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy or C 1 -C 5 alkylthio;

each R 3 is independently H, halogen, C 1 -C 5 alkyl, C 1 -C 5 haloalkyl, C 1 -C 5 alkoxy or C 1 -C 5 haloalkoxy;

n is 0 or 1;

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

L is a direct bond;

G is H, C(═O)R 9 , CO 2 R 10 , CON(R 11 )(R 12 ) or P(═O)(R 13 )(R 14 ); or C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkoxyalkyl, C 3 -C 6 cycloalkyl or C 4 -C 7 cycloalkylalkyl;

R 9 and R 11 are independently H, C 1 -C 7 alkyl or C 3 -C 7 alkenyl; or phenyl, benzyl, each phenyl or benzyl optionally substituted by halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

R 10 is C 1 -C 7 alkyl or C 3 -C 7 cycloalkyl; or phenyl or benzyl, each phenyl or benzyl optionally substituted by halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

R 12 is H, C 1 -C 7 alkyl or C 3 -C 7 cycloalkyl;

R 13 is C 1 -C 2 alkyl or C 1 -C 2 alkoxy; and

R 14 is C 1 -C 2 alkyl or C 1 -C 2 alkoxy.

4. The compound of claim 3 wherein

R 1 is H, C 1 -C 7 alkyl, C 4 -C 7 alkylcycloalkyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl or C 2 -C 7 alkoxyalkyl;

R 2 is H, halogen, cyano, C 1 -C 7 alkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy or C 1 -C 5 alkylthio;

each R 3 is independently H, halogen, methyl, ethyl, CF 3 or —OCHF 2 ;

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

G is H, C(═O)R 9 , CO 2 R 10 or P(═O)(R 13 )(R 14 ); or C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkoxyalkyl or C 3 -C 6 cycloalkyl;

R 9 is H or C 1 -C 7 alkyl; or benzyl optionally substituted by halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; and

R 10 is C 1 -C 7 alkyl; or phenyl optionally substituted by halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl.

5. The compound of claim 4 wherein

R 1 is H, C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl or C 2 -C 7 alkoxyalkyl;

R 2 is H, halogen, cyano, C 1 -C 7 alkyl, C 1 -C 7 haloalkyl or C 1 -C 7 alkoxy;

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

R 4 is H, F, Cl, Br or methyl;

R 5 is H or methyl;

R 6 is H or methyl;

R 7 is H or methyl;

R 8 is H or methyl;

G is H, C(═O)R 9 or CO 2 R 10 ; or C 2 -C 4 alkoxyalkyl or C 3 -C 6 cycloalkyl;

R 9 is C 1 -C 7 alkyl; or benzyl optionally substituted by halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; and

R 10 is CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , Ph, Ph(4-Cl), Ph(3-CF 3 ) or Ph(4-CF 3 ).

6. The compound of claim 5 wherein

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

R 2 is H, Cl, Br, I, cyano, methyl, CF 3 or methoxy;

n is 0;

R 4 is methyl;

R 5 is H;

R 6 is H;

R 7 is H;

R 8 is H; and

G is H.

7. A compound of claim 1 that is 4-(3,4-dihydro-2-methyl-1-naphthalenyl)-5-hydroxy-2,6-dimethyl-3-(2H)-pyridazinone.

8. 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.

Continuity (2)
Provisional Application 62527523 · Jun 30, 2017
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