BR-122026002514-A2 - PROCESSES FOR PREPARING A COMPOUND

BR122026002514A2BR 122026002514 A2BR122026002514 A2BR 122026002514A2BR-122026002514-A2

Abstract

Compounds of formula I and N-oxides or salts thereof are disclosed, wherein R1 is C1-C4 alkyl or C3-C6 cycloalkyl; 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; provided that (a) when R3 is OR4 and R4 and R5 are both H, then R6 is Cl; and (b) when R2 is Br, R3 is OR4, and R4 is H, then R6 is H. A composition containing a compound of formula I and methods for controlling unwanted vegetation comprising contacting the unwanted vegetation or its environment with an effective amount of a compound of formula I or a composition thereof are also disclosed. Methods for preparing a compound of formula I are also presented.

Inventors

THOMAS PAUL SELBY
THOMAS MARTIN STEVENSON
STEPHEN FREDERICK MCCANN
ERIC ALLEN MARSHALL
Yuzhong Chen

Assignees

FMC CORPORATION

Dates

Publication Date: 20260310
Application Date: 20190926
Priority Date: 20180927

Claims (2)

1. PROCESS FOR PREPARING A COMPOUND of formula IA: wherein: R1 is CH3; R2 is Cl; R5 is F, Cl or CH3; and R6 is H; the process characterized by comprising: (1) reacting a compound of formula II: where: R5 is F, Cl, or CH3; and R6 is H; with magnesium to form an intermediate compound of formula III: (2) react the intermediate compound of formula III formed in (1) with a compound of formula IV-B: IV-B where: R1 is CH3; G is C1-C4 alkyl, SO2CF3 or SO2(4-Me-Ph).
2. PROCESS FOR PREPARING A COMPOUND with formula IE: IE wherein: R1 is CH3; R5 is F, Cl or CH3; and R6 is H; process characterized by comprising: (1) reacting a compound of formula II: where: R5 is F, Cl, or CH3; and R6 is H; with magnesium to form an intermediate compound of formula (2) react the intermediate compound of formula III formed in (1) with a compound of formula 7: where: R1 is CH3.

Description

FIELD OF THE INVENTION AND BACKGROUND OF THE INVENTION [001] The present invention provides pyridazinones and processes for the preparation of pyridazinones. The pyridazinones disclosed herein can be used as synthetic intermediates to prepare pyridazinone-based herbicides or used as pyridazinone herbicides. WO 2015/168010 and WO 2017/074988 disclose herbicidal pyridazinones and synthetic intermediates used to prepare herbicidal pyridazinones. There is a need for improved herbicidal pyridazinones and improved methods for preparing herbicidal pyridazinones. BRIEF DESCRIPTION OF THE INVENTION [002] In one aspect, the present invention provides a compound of formula I and N-oxides or salts thereof, I where: R1 is C1-C4 alkyl or C3-C6 cycloalkyl; 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. [003] In another aspect, the present invention provides a process for the preparation of a compound of formula IA: IA wherein: R1 is C1-C4 alkyl or C3-C6 cycloalkyl; R2 is H or Cl; R5 is H, F, Cl or CH3; and R6 is H or Cl; the process comprising: (1) reacting a compound of formula II: where: R5 is H, F, Cl, or CH3; and R6 is H or Cl; with magnesium to form an intermediate compound of formula III: (2) react the intermediate compound of formula III formed in (1) with a compound of formula IV-A or IV-B: where: R1 is C1-C4 alkyl or C3-C6 cycloalkyl; G is C1-C4 alkyl, SO2CF3 or SO2(4-Me-F). [004] In another aspect, the present invention provides a process for the preparation of a compound of formula IB: wherein: R1 is C1-C4 alkyl or C3-C6 cycloalkyl; R5 is H, F, Cl or CH3; and R6 is H or Cl; the process comprising reacting a compound of formula IA, as defined above wherein R2 is H, with a methoxylation agent. [005] In another aspect, the present invention provides a process for the preparation of a compound of formula IC: RÍ wherein: R1 is C1-C4 alkyl or C3-C6 cycloalkyl; R2 is Cl, Br or I; R5 is H, F, Cl or CH3; and R6 is H or Cl; the process comprising: (1) reacting a compound of formula IB, as defined above, with a tmp-zinc base, to form a zincated intermediate compound of formula V: (2) react the zinc-coated intermediate compound of formula V formed in (1) with a halogenating agent. [006] In another aspect, the present invention provides a process for the preparation of a compound of formula ID: ID wherein: R1 is C1-C4 alkyl or C3-C6 cycloalkyl; R2 is Cl, Br or I; R5 is H, F, Cl or CH3; and R6 is H or Cl; the process comprising reacting a compound of formula IC, as defined above, with a demethylating agent. [007] In another aspect, the present invention provides a further process for the preparation of a compound of formula IE: IE where: R1 is C1-C4 alkyl or C3-C6 cycloalkyl; R5 is H, F, Cl or CH3; and R6 is H or Cl; the process comprising reacting a compound of formula VI: VI wherein: R1 is C1-C4 alkyl or C3-C6 cycloalkyl, R5 is H, F, Cl or CH3; and R6 is H or Cl; with phosphorus oxychloride. [008] In another aspect, the present invention provides a further process for the preparation of a compound of formula IE: IE where: R1 is C1-C4 alkyl or C3-C6 cycloalkyl; R5 is H, F, Cl or CH3; and R6 is H or Cl; the process comprising: reacting a compound of formula II: where: R5 is H, F, Cl, or CH3; and R6 is H or Cl; with magnesium to form an intermediate compound of formula III: (2) react the intermediate compound of formula III formed in (1) with a compound of formula 7: R1 is C1-C4 alkyl or C3-C6 cycloalkyl. DETAILED DESCRIPTION OF THE INVENTION [009] As used herein, the terms “comprises”, “comprising”, “includes”, “including”, “has”, “having”, “contains”, “containing”, “characterized by”, or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly stated. For example, a process or method comprising a list of elements is not necessarily limited to only those elements, but may include other elements not expressly listed or inherent to such process or method of composition. [010] The transition phrase “consisting of” excludes any unspecified element, step, or ingredient. If included in the claim, this would terminate the claim for the inclusion of other materials besides those mentioned, except for impurities normally associated with them. When the phrase “consisting of” appears in a clause within the body of a claim, rather than immediately following the preamble, it limits only the element established in that clause; other elements are not excluded from the claim as a whole. [011] The transitional phrase “essentially consisting of” is used to define a process or method that includes materials, steps, features, components, or elements in addition to those literally disclosed, provided that these additional materials, steps, features, components, or elements do not materially affect the basic and innovative features of the disclosure. The term “essentially consisting of” occupies a middle ground betwee