Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
  • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
  • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
  • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D237/22—Nitrogen and oxygen atoms
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
  • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
  • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
  • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D237/14—Oxygen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
  • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
  • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
  • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D237/14—Oxygen atoms
  • C07D237/16—Two oxygen atoms

Definitions

• the present disclosure provides pyridazinones and a process for preparing pyridazinones.
• the pyridazinones disclosed herein can be used as synthetic intermediates to prepare pyridazinone-based herbicides.
• WO 2015/168010 and WO 2017/074988 disclose herbicidal pyridazinones and synthetic intermediates used to prepare herbicidal pyridazinones. There exists a need for improved methods of preparing herbicidal pyridazinones.
• the present disclosure provides a compound of Formula I and A -oxides or salts thereof,
• R 1 is C l- C 4 alkyl or C 3- C 6 cycloalkyl
• R 2 is Cl or NH 2 ;
• R 3 is Cl or OR 4 ;
• R 4 is -C4 alkyl, S0 2 CF 3 or S0 2 (4-Me-Ph).
• the present disclosure provides a process for preparing a compound of Formula I- A,
• R 1 is C 3- C 4 alkyl or C 3- C 6 cycloalkyl
• R 4 is C !- C 4 alkyl
• R 1 is C 3- C 4 alkyl or C 3- C 6 cycloalkyl
• the present disclosure provides a process for preparing a compound ofFormula l-B
• R 1 is C 3- C 4 alkyl or C 3- C 6 cycloalkyl
• R 4 is C !- C 4 alkyl
• 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 indicated.
• a process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition process or method.
• transitional phrase“consisting of’ excludes any element, step, or ingredient not specified. If in the claim, this phrase excludes materials other than those expressly recited except for impurities ordinarily associated therewith.
• phrase“consisting of’ appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.
• transitional phrase“consisting essentially 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 novel characteristic(s) of the disclosure.
• the term “consisting essentially of’ occupies a middle ground between“comprising” and“consisting of’.
• “or” refers to an inclusive or and not to an exclusive or.
• a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).
• indefinite articles“a” and“an” preceding an element or component of the disclosure are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore“a” or“an” should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular.
• C j- Cg alkyl includes straight-chain or branched alkyl groups having one to six carbon atoms, e.g., methyl, ethyl, «-propyl, /-propyl, or the different butyl, pentyl, or hexyl isomers.
• the term“C1-C4 alkyl” includes straight-chain or branched alkyl having one to four carbon atoms, e.g., methyl, ethyl, «-propyl, /-propyl, or the different butyl isomers
• the term“C1-C3 alkyl” includes methyl, ethyl, «-propyl, and /-propyl.
• the term“C3-C6 cycloalkyl” includes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
• the term“halogen” includes fluorine, chlorine, bromine and iodine.
• reacting refers to adding, contacting, or mixing two or more reagents under appropriate conditions to produce the indicated and/or the desired product. It should be appreciated that the reaction which produces the indicated and/or the desired product may not necessarily result directly from the combination of two reagents which were initially added, i.e. there may be one or more intermediates which are produced in the mixture which ultimately leads to the formation of the indicated and/or the desired product. Reacting can take place in the presence or absence of solvent, at a temperature above room temperature or below room temperature, under an inert atmosphere, etc.
• Pressure is defined as the pressure measured relative to the ambient atmospheric pressure.
• psig pounds per square inch gague.
• alkoxylating agent refers to a chemical reagent used to add a C1-C4 alkoxy group to a compound.
• C [- C 4 alkoxy” includes methoxy, ethoxy, //-propyl oxy, isopropyloxy and the different butoxy isomers.
• Exemplary non-limiting alkoxylating agents include sodium methoxide and sodium ethoxide.
• methoxylating agent refers to a chemical reagent used to add a methoxy group, i.e. OCH3, to a starting compound.
• alkyl nitrite refers to a compound having the formula R-ONO, wherein R is a C j- Cg alkyl.
• exemplary non-limiting alkyl nitrites include tert- butyl nitrite, amyl nitrite and //-butyl nitrite.
• R 4 is“S0 2 (4-Me-Ph)” this is alternatively defined as“S0 2 ( /-tolyl).”
• compounds of Formula I typically exist in more than one solid form.
• compounds of Formula I include all crystalline and non-crystalline forms of the compounds within the genus represented by Formula I.
• Non-crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts.
• Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types).
• polymorph refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and/or conformations of the molecules in the crystal lattice.
• polymorphs can have the same chemical composition, they can also differ in composition due the presence or absence of co crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability.
• a polymorph of a compound of Formula I can exhibit beneficial effects (e.g., suitability for improved solubility) relative to another polymorph or a mixture of polymorphs of the same compound of Formula I.
• Preparation and isolation of a particular polymorph of a compound of Formula I can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures.
• crystallization using selected solvents and temperatures.
• N- oxides of heterocycles and tertiary amines are well known by one skilled in the art.
• Exemplary procedures for preparing N- oxides include the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and w-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as /-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane.
• MCPBA peroxy acids
• alkyl hydroperoxides such as /-butyl hydroperoxide
• sodium perborate sodium perborate
• dioxiranes such as dimethyldioxirane.
• salts of the compounds disclosed here can be isolated using the present process or processes depending on the base utilized in the method to prepare the compounds.
• Suitable salts include acid- addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
• Embodiment Al A compound of Formula I and A -oxides or salts thereof as described in the Summary of the Invention.
• Embodiment A2 The compound of Embodiment Al wherein R 1 is C ]- C 4 alkyl.
• Embodiment A3 The compound of Embodiment Al wherein R 1 is C3-C6 cycloalkyl.
• Embodiment A4 The compound of any one of Embodiments Al to A2 wherein R 1 is methyl or ethyl.
• Embodiment A5 The compound of Embodiment A4 wherein R 1 is methyl.
• Embodiment A6 The compound of any one of Embodiments Al to A5 wherein R 2 is Cl.
• Embodiment A7 The compound of any one of Embodiments Al to A5 wherein R 2 is NH 2.
• Embodiment A8 The compound of any one of Embodiments Al to A7 wherein R 3 is Cl.
• Embodiment A9 The compound of any one of Embodiments Al to A7 wherein R 3 is OR 4 .
• Embodiment A10 The compound of Embodiment A9 wherein R 4 is C1-C4 alkyl.
• Embodiment Al l The compound of Embodiment A10 wherein R 4 is methyl, ethyl, «-propyl or /-propyl.
• Embodiment A12 The compound of Embodiment A9 wherein R 4 is SO2CF3 or
• Embodiment A13 A compound of Formula I in the Summary of the Invention that is a compound of Formula I-A
• R 1 is C 3- C 4 alkyl or C 3- C 6 cycloalkyl
• R 3 is OR 4 ;
• R 4 is C !- C 4 alkyl.
• Embodiment A14 A compound of Formula I in the Summary of the Inveniton that is a compound Formula I-B
• R 1 is C 3- C 4 alkyl or C 3- C 6 cycloalkyl
• R 4 is C !- C 4 alkyl.
• Embodiment A15 A compound of Formula I in the Summary of the Invention that is a compound Formula I-C
• R 1 is C 3- C 4 alkyl or C 3- C 6 cycloalkyl.
• Embodiment A16 A compound of any one of Embodiments Al, A2, A4 or A6 through A15 wherein R 1 is methyl.
• Embodiment A17 A compound of any one of Embodiments Al through A5 or A-6 through A16 wherein R 2 is other than Cl (i.e. is other than a compound of Formula I-B or I-C).
• Embodiment A18 A compound of Embodiment Al that is other than 4,5,6-trichloro-2- m ethyl-3 (2F/)-pyridazinone (CAS No. 37648-42-3) and 6-amino-4,5-dichloro-2- m ethyl-3 (2F/)-pyridazinone (CAS No. 25717-64-0).
• Embodiment Bl A process for preparing a compound of Formula I-A as described in the Summary of the Invention.
• Embodiment B2 The process of Embodiment Bl wherein R 1 is C ⁇ -C ⁇ cycloalkyl.
• Embodiment B3 The process of Embodiment Bl wherein R 1 is C1-C4 alkyl.
• Embodiment B4 The process of Embodiment B 1 or B3 wherein R 1 is methyl.
• Embodiment B5 The process of any one of Embodiments Bl to B4 wherein the reacting is performed in a suitable solvent.
• Embodiment B6 The process of Embodiment B5 wherein the suitable solvent is
• Embodiment B7 The process of any one of Embodiments Bl to B6 wherein the reacting is performed at a temperature at or below 0 °C.
• Embodiment B8 The process of any one of Embodiments Bl to B6 wherein the reacting is performed at a temperature above 0 °C.
• Embodiment B9 The process of any one of Embodiments Bl to B8 wherein the
• alkoxylating agent is sodium methoxide or potassium methoxide.
• Embodiment B 10 The process of any one of Embodiments Bl and B3 to B9 wherein R 1 is methyl.
• Embodiment Bl 1. The process of any one of Embodiments Bl to B10 wherein the
• Embodiment Cl A process for preparing a compound of Formula I-B as described in the Summary of the Invention.
• Embodiment C2 The process of Embodiment Cl wherein R 1 is C 3- C 6 cycloalkyl.
• Embodiment C The process of Embodiment Cl wherein R 1 is C1-C4 alkyl.
• Embodiment C The process of any one of Embodiments Cl or C3 wherein R 1 is
• Embodiment C5. The process of any one of Embodiments Cl to C4 wherein R 4 is
• Embodiment C6 The process of any one of Embodiments Cl to C5 wherein the reacting is performed in a suitable solvent.
• Embodiment C7 The process of Embodiment C6 wherein the suitable solvent is acetonitrile.
• Embodiment C8 The process of any one of Embodiments Cl to C7 wherein the reacting is performed at a temperature at or below 0 °C.
• Embodiment C9 The process of any one of Embodiments Cl to C7 wherein the reacting is performed at a temperature above 0 °C.
• Embodiment C10 The process of any one of Embodiments Cl through C9 wherein the alkyl nitrite is tert- butyl nitrite.
• Embodiment Cl 1. The process of any one of Embodiments Cl to C6 or C9 to C10
• Embodiment C12 The process of Embodiment Cl 1 wherein the reacting is performed at a temperature between 0 °C and 80 °C.
• Embodiment C13 The process of any one of Embodiments Cl, C3 or C5 through C12 wherein R 1 is methyl.
• Embodiment C14 The process of any one of Embodiments Cl to C13 wherein the
• Embodiment Dl A process for preparing a compound of Formula I-C as described in the Summary of the Invention.
• Embodiment D2 The process of Embodiment Dl wherein R 1 is C3-C cycloalkyl.
• Embodiment D3 The process of Embodiment Dl wherein R 1 is C1-C4 alkyl.
• Embodiment D4 The process of Embodiment Dl or D3 wherein R 1 is methyl.
• Embodiment D5 The process of any one of Embodiments Dl to D4 wherein the
• reacting is performed neat or in a suitable solvent.
• Embodiment D6 The process of Embodiment D5 wherein the suitable solvent is
• Embodiment D7 The process of Embodiment D5 wherein the reacting is performed neat.
• Embodiment D8 The process of any one of Embodiments Dl to D7 wherein the
• reacting is performed at a temperature between 80 °C and 150 °C.
• Embodiment D9 The process of any one of Embodiment D8 wherein the reacting is performed at a temperature between 100 °C and 140 °C.
• Embodiment D10 The process of Embodiment D8 wherein the reacting is performed at a temperature between 120 °C and 140 °C.
• Embodiment Dl l The process of Embodiment D8 wherein the reacting is performed at a temperature between 100 °C and 120 °C.
• Embodiment D12 The process of Embodiment D8 wherein the reacting is performed at a temperature of 120 °C.
• Embodiment D13 The process of Embodiment D8 wherein the pressure at 100 °C is up to 117 psig (807 kPa).
• Embodiment D14 The process of Embodiment D8 wherein the pressure at 120 °C is up to 150 psig (1034 kPa).
• Embodiment D15 The process of Embodiment D8 wherein the pressure at 140 °C is up to 223 psig (1538 kPa).
• Embodiment D16 The process of any one of Embodiments Dl to D9 wherein the
• Embodiment D17 The process of Embodiment D 10 wherein the reacting is in the
• Embodiment D18 The process of Embodiment Dl 1 wherein the reacting is in the
• Embodiment D19 The process of any one of Embodiments Dl to D12 wherein the
• Embodiments Al through A18, Bl through B l l, Cl through C14 and Dl through D19 and any other Embodiment or Embodiments described herein can be combined in any manner.
• a compound of Formula I-B can be prepared by the reaction of a trichloropyridazinone compound of Formula I-C with either sodium or potassium alkoxide in a solvent such as l,4-dioxane or tetrahydrofuran at temperatures ranging from 0 °C up to the reflux temperature of the solvent as depicted in Scheme 1.
• a solvent such as l,4-dioxane or tetrahydrofuran
• a compound of Formula I-C can alternatively be prepared by the chlorination of a compound of Formula 3 (wherein M is H, Na or K) using one or more chlorinating reagents, such as POCI3, PCI3, PCI5 and combinations thereof.
• the reaction is conducted neat in the chlorinating reagent, or in the combination of chlorinating reagents, at 80 °C to 150 °C, preferably around 100 °C.
• a compound of Formula 3 can be prepared by treatment of a compound of Formula 4 with sodium or potassium alkoxide in an organic solvent, such as methanol, ethanol, isopropanol or tetrahydrofuran.
• an organic solvent such as methanol, ethanol, isopropanol or tetrahydrofuran.
• the reaction is conducted at 60 °C to 150 °C, preferably 70 °C to 80 °C.
• non-alcoholic solvents such as tetrahydrofuran
• the reaction is conducted at 0 °C to 20 °C, preferably 0 °C to 5 °C.
• the method of Scheme 3 is illustrated in present Synthesis Example 3.
• a compound of Formula I-C can also be prepared from maleic anhydride in two steps as described in WO 8704321 A2 and JP47024029B and as shown in Scheme 4.
• Alternative conditions for the second reaction of Scheme 4 include using one or more chlorinating reagents, such as POCl 3 , PCl 3 , PCl 5 and combinations thereof in the presence of A f , A-di m ethyl form am i de in a sealed reactor.
• the reaction is conducted neat at 80 °C to 150 °C, preferably 100 °C to 120 °C.
• the amount of A f , A'-di m ethyl form am i de can be from 10 mol% to 100 mol%, preferably 20 mol% to 30 mol%.
• the reaction can be conducted neat or in an organic solvent, such as acetonitrile.
• the second reaction of Scheme 4 is illustrated in present Synthesis Example 4.
• a compound of Formula I-B can be prepared using the procedures depicted in Scheme 5.
• An amino-pyridazinone compound of Formula I-A can be treated with an alkyl nitrite, such as tert-butyl nitrite or isoamyl nitrite, and either CuCl or CuCl 2 in a solvent such as acetonitrile at temperatures ranging from 0 °C to the refluxing temperature of the solvent.
• an analogous procedure can be found on page 82 in WO2010/009183.
• Alternative conditions for the reaction in Scheme 5 include reacting a compound of Formula I-A with sodium nitrite and concentrated hydrochloric acid, optionally in a solvent such as acetonitrile.
• An analogous procedure can be found on page 223 in W02012/091156.
• the preparation of a compound of Formula I-A can be achieved by the treatment of a compound of Formula 5 with sodium alkoxide in dioxane as depicted in Scheme 6.
• sodium alkoxide 1.0-1.5 molar equivalents
• a solution of Compound 5 in dioxane can be added to a solution of Compound 5 in dioxane, and the resulting mixture can be stirred at a temperature of preferably 10 °C up to the reflux temperature of the solvent.
• the preparation of a compound of Formula 5 is described in J Het. Chem. 1996, vol. 33, p. 1915. See also J. Het. Chem. 1996, vol. 33, p. 1579.
• R 1 is C 3- C 4 alkyl or C 3- C 6 cycloalkyl
• R 2 is Cl
• R 3 is Cl or OR 4 ;
• R 4 is - alkyl, S0 2 CF 3 or S0 2 (4-Me-Ph);
• R 5 is H, F, Cl or CH 3 ;
• R 6 is H or Cl
• R 1 is C 3- C 4 alkyl or C 3- C 6 cycloalkyl;
• R 2 is Cl;
• R 5 is H, F, Cl or CH 3 ;
• R 6 is H or Cl.
• a compound of Formula IV can further be reacted with a methoxylating agent to prepare a compound of Formala V
• R 1 is C!-C 4 alkyl or C 3- C 6 cycloalkyl
• R 2 is Cl
• R 5 is H, F, Cl or CH 3 ;
• R 6 is H or Cl
• a compound of Formula V can be reacted with a dem ethylating agent (such as morpholine) to prepare a compound of Formula VI
• R 1 is C 3— C 4 alkyl or C 3- C 6 cycloalkyl
• R 2 is Cl
• R 5 is H, F, Cl or CH 3 ;
• R 6 is H or Cl.
• R 1 is methyl.
• R 5 is H.
• R 5 is CH 3.
• R 6 is H.
• Compounds of Formula VI are known from WO 2015/168010 to posess herbicidal activity.
• a solution of sodium methoxide in methanol (4.8 mL of a 4.4 M solution, 21.0 mmol) was added to a suspension of 6-ami no-4 , 5 -di chi oro-2-methyl -3 (2//)-pyridazi none (3 . 70 g, 19.1 mmol) and dioxane (95 mL, anhydrous) with ice-water bath cooling.
• the resulting suspension was stirred at ambient temperature for 3 h and was then poured into a saturated aqueous ammonium chloride solution (150 mL) and the resulting mixture was extracted with methylene chloride (150 mL).

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