Pyridazinone herbicides and pyridazinone intermediates used to prepare a herbicide
AssigneeFMC Corporation
InventorsThomas Paul Selby, Thomas Martin Stevenson, Stephen Frederick McCann, Eric Allen Marshall, Yuzhong Chen
Life of this patent
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Abstract
Disclosed are compounds of Formula I and N-oxides or salts thereof, wherein R1 is C1-C4alkyl or C3-C6cycloalkyl; R2 is H, Cl, Br or I; R3 is Cl or OR4; R4 is H or C1-C4 alkyl; R5 is H, F, Cl or CH3; and R6 is H or Cl. Also disclosed is a composition containing a compound of Formula I, and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound of Formula I or a composition thereof. Also disclosed are methods for preparing a compound of Formula I.
Claims17
A compound of Formula I and N-oxides or salts thereof,
- wherein
- R1 is C1-C4 alkyl or C3-C6 cycloalkyl;
- R2 is Cl;
- R3 is Cl or OR4;
- R4 is H or C1-C4 alkyl;
- R5 is F, Cl or CH3;
- and
- R6 is H.
A process for preparing a compound of Formula I-A,
- wherein
- R1 is C1-C4 alkyl or C3-C6 cycloalkyl;
- R2 is Cl;
- R5 is F, Cl or CH3;
- and
- R6 is H;
- the process comprising:
- (1) reacting a compound of Formula II
- wherein
- R5 is F, Cl or CH3;
- and
- R6 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
- R1 is C1-C4 alkyl or C3-C6 cycloalkyl;
- G is C1-C4 alkyl, SO2CF3 or SO2 (4-Me-Ph).
A process for preparing a compound of Formula I-C
- wherein
- R1 is C1-C4 alkyl or C3-C6 cycloalkyl;
- R2 is Cl;
- R5 is F, Cl or CH3;
- and
- R6 is H;
- the process comprising:
- (1) reacting a compound of Formula I-B,
- wherein
- R1 is C1-C4 alkyl or C3-C6 cycloalkyl;
- R5 is F, Cl or CH3;
- and
- R6 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.
A process for preparing a compound of Formula I-D
- wherein
- R1 is C1-C4 alkyl or C3-C6 cycloalkyl;
- R2 is Cl;
- R5 is F, Cl or CH3;
- and
- R6 is H;
- the process comprising reacting a compound of Formula I-C,
- wherein
- R1 is C1-C4 alkyl or C3-C6 cycloalkyl;
- R2 is Cl;
- R5 is F, Cl or CH3;
- and
- R6 is H;
- with a demethylating agent.
A process for preparing a compound of Formula I-E
- wherein
- R1 is C1-C4 alkyl or C3-C6 cycloalkyl;
- R5 is F, Cl or CH3;
- and
- R6 is H;
- the process comprising reacting a compound of Formula VI
- wherein
- R1 is C1-C4 alkyl or C3-C6 cycloalkyl;
- R5 is F, Cl or CH3;
- and
- R6 is H;
- with phosphorous oxychloride.
A process for preparing a compound of Formula I-E
- wherein
- R1 is C1-C4 alkyl or C3-C6 cycloalkyl;
- R5 is F, Cl or CH3;
- and
- R6 is H;
- the process comprising:
- (1) reacting a compound of Formula II
- wherein
- R5 is F, Cl or CH3;
- and
- R6 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
- R1 is C1-C4 alkyl or C3-C6 cycloalkyl.
Dependencies are inferred from the claim text.