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BR-112021005787-B1 - COMPOUND, HERBICIDE COMPOSITIONS, HERBICIDE MIXTURE AND METHOD FOR CONTROLLING THE GROWTH OF UNWANTED VEGETATION

BR112021005787B1BR 112021005787 B1BR112021005787 B1BR 112021005787B1BR-112021005787-B1

Abstract

COMPOUND, PROCESSES FOR PREPARING A COMPOUND, HERBICIDE COMPOSITIONS, HERBICIDE MIXTURE AND METHOD FOR CONTROLLING THE GROWTH OF UNDESIRABLE VEGETATION. 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; (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
20260317
Application Date
20190926
Priority Date
20180927

Claims (11)

  1. 1. COMPOUND, characterized by having the formula I and N-oxides or salts thereof, where R1 is CH3; R2 is Cl; R3 is OR4; R4 is H; R5 is F, Cl or CH3; and R6 is H.
  2. 2. COMPOUND, as characterized by R5 being CH3.
  3. 3. COMPOUND, characterized as being selected from the group consisting of 6-chloro-4-(2,7-dimethyl-1-naphthalenyl)-5-hydroxy-2-methyl-3(2H)-pyridazinone; 6-chloro-4-(7-fluoro-2-methyl-1-naphthalenyl)-5-hydroxy-2-methyl-3(2H)-pyridazinone; and 6-chloro-4-(7-chloro-2-methyl-1-naphthalenyl)-5-hydroxy-2-methyl-3(2H)-pyridazinone.
  4. 4. HERBICIDAL COMPOSITION, characterized by comprising the compound, as defined in claim 1, and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.
  5. 5. HERBICIDAL COMPOSITION, characterized by comprising a compound, as defined in claim 1, at least one additional active ingredient selected from the group consisting of other herbicides and herbicide plant protectants and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.
  6. 6. HERBICIDAL MIXTURE, characterized by comprising (a) a compound, as defined in claim 1, and (b) at least one additional active ingredient.
  7. 7. MIXTURE, according to claim 6, characterized in that said (b) at least one additional active ingredient is selected from the group consisting of 5-chloro-2-[3-chloro-2-[3-(difluoromethyl)-5-isoxazolyl]phenoxy]-pyrimidine, 1-[2-chloro-6-[(5-chloro-2-pyrimidinyl)oxy]phenyl]-4,4,4-trifluoro-1-butanone, 2,4-D, acetochlor, acifluorfen, atrazine, carfentrazone, chlorimuron, clethodim, clomazone, clopyralide, chloransulam-methyl, dicamba, diflufenican, dimethenamide, diquat, flumioxazin, fluroxypyr, flutiacet-methyl, fomesafen, glufosinate, glyphosate, imazethapyr, isoxaflutol, lactofen, mesotrione, metribuzin, piroxasulfone, rimsulfuron, saflufenacil, S-metolachlor, sulfentrazone, tembotrione, thiencarbazone, tolpiralate, topramezone, benoxacor, isoxadiphenethyl, cloquintocet-mexyl and mefenpyr-diethyl.
  8. 8. MIXTURE, according to claim 7, characterized in that (b) at least one additional active ingredient is selected from the group consisting of 5-chloro-2-[3-chloro-2-[3-(difluoromethyl)-5-isoxazolyl]phenoxy]-pyrimidine, atrazine, glyphosate, saflufenacil, piroxasulfone, 1-[2-chloro-6-[(5-chloro-2-pyrimidinyl)oxy]phenyl]-4,4,4-trifluoro-1-butanone, metribuzin and rimsulfuron.
  9. 9. MIXTURE, according to claim 7, characterized in that (b) at least one additional active ingredient is selected from the group consisting of benoxacor, isoxadifen-ethyl, cloquintocet-mexil and mefenpyr-diethyl.
  10. 10. MIXTURE, according to claim 7, characterized in that (b) at least one additional active ingredient is selected from the group consisting of S-metolachlor, sulfentrazone, clomazone, chlorimuron, fomesafen, flumioxazin, fluroxypyr, 2,4-D, isoxaflutol, diflufenican, mesotrione, topramezone, tolpyralate, dicamba, carfentrazone, clopyralide, acetochlor and thiencarbazone.
  11. 11. METHOD FOR CONTROLLING THE GROWTH OF UNDESIRABLE VEGETATION, characterized by comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound, as defined in claim 1.

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, 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 where 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 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 wherein R1 is C1-C4 alkyl or C3-C6 cycloalkyl; R is Cl, Br or I; R5 is H, F, Cl or CH3; and R6 is H or Cl, a 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 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 where 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, a 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 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 VI where 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 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: (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 7 where 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 between “comprising” and “consisting of”. [012] When depositors define a disclosure or a part thereof with an open-ended t