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WO2025190803A1 - Procédé permettant d'obtenir des (e)-2-[2-(halométhyl)-3-méthyl-phényl]-3-méthoxy-prop-2-énoates de méthyle et des intermédiaires de ceux-ci - Google Patents

Procédé permettant d'obtenir des (e)-2-[2-(halométhyl)-3-méthyl-phényl]-3-méthoxy-prop-2-énoates de méthyle et des intermédiaires de ceux-ci

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Publication number
WO2025190803A1
WO2025190803A1 PCT/EP2025/056288 EP2025056288W WO2025190803A1 WO 2025190803 A1 WO2025190803 A1 WO 2025190803A1 EP 2025056288 W EP2025056288 W EP 2025056288W WO 2025190803 A1 WO2025190803 A1 WO 2025190803A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
process according
formula
reaction
methyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/EP2025/056288
Other languages
English (en)
Inventor
Kailaskumar Borate
Rahul Kaduskar
Rakesh RATH
Raju THOMBAL
Nataliia SHYMANSKA
Harish SHINDE
Roland Goetz
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BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Priority claimed from EP24172986.2A external-priority patent/EP4644358A1/fr
Application filed by BASF SE filed Critical BASF SE
Publication of WO2025190803A1 publication Critical patent/WO2025190803A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/76—Benzo[c]pyrans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers

Definitions

  • the present invention relates to a process for preparation of methyl (E)-2-[2-halomethyl)-3- methyl-phenyl]-3-methoxy-prop-2-enoates intermediates for the preparation of substituted enol ether fungicides.
  • the invention also relates to novel intermediates for the preparation of substituted methyl (E)-3-methoxy-2-[3-methyl-2-[[(E)-1-(het)arylethylideneamino]oxymethyl]- phenyl]prop-2-enoates.
  • Such substituted methyl (E)-3-methoxy-2-[3-methyl-2-[[(E)-1-(het)arylethylideneamino]oxy- methyl]phenyl]prop-2-enoates are known as fungicides from WO 2021/153754, WO 2021/219386, WO 2021/219387, WO 2021/219388, WO 2021/219390, WO 2021/249928; WO 2022/008303, WO 2022/013009, WO 2022//03390, WO 2023/072670, WO 2023/072671 , WO 2023/072672 and EP 4242198.
  • the preparation of fungicidal compounds is described in the abovementioned references inter alia by a coupling of the intermediates of the formula inter alia with substituted benzaldehyde oxime compounds.
  • New methods are desirable for preparing methyl (E)-2-[2-(halomethyl)-3-methyl-phenyl]-3- methoxy-prop-2-enoates useful as intermediates.
  • the present invention relates to a process for preparing the compound of formula II the process comprising: first, a base selected from alkali metal and alkaline earth metal methoxides dissolved in methanol and an inert solvent are mixed; second, to this mixture is added the compound of formula IV and a formylating agent; to produce the compound of formula III and/or the alkali metal and alkaline earth metal salt thereof, third, reacting the compound of formula III with an alkylating agent, preferably in the presence of a solvent and a base, optionally in the presence of a catalyst, wherein methanol is removed from the mixture either before the addition of compound IV and/or the formylating agent, or after the compound III was produced and before the compound III is reacted with an alkylating agent.
  • the first formylation reaction requires the presence of a base selected from alkali metal and alkaline earth metal methoxides, such as sodium methoxide and potassium methoxide; even more preferably an alkali metal methoxide is used, in particular sodium methoxide.
  • the methoxide base is dissolved in methanol, preferably sodium methoxide dissolved in methanol which is commercially available.
  • the base dissolved in methanol can be mixed with an inert solvent prior to the reaction.
  • the base is usually provided in excess of compounds IV, preferable 1.1-10 molar equivalents; more preferably 1.1-5 molar eq. of compounds IV; and even more preferably 1.1-3 molar eq..
  • Suitable inert solvents for the formylation reaction are xylene, benzene, chlorobenzene, fluorobenzene, cumene, p-cymene or toluene, preferably toluene.
  • Suitable formylating agents are formic acid ester, methyl formate, ethyl formate, propyl formate, isopropyl formate, butyl formate and t-butyl formate, preferably methyl formate.
  • the formylating agent is usually provided in excess of compounds IV, preferable 1.1-10 molar equivalents; more preferably 1.1-5 molar eq. of compounds IV; and even more preferably 1.1-3 molar eq..
  • the formylating agent and the compound IV can be added to the mixture simultaneously or consecutively.
  • the compound IV and/or the formylating agent are dissolved in the abovementioned inert solvent; even more preferably compound IV and the formylating agent are dissolved in such inert solvent.
  • the compound of formula III produced by the formylation reaction comprises not also its alkali metal and alkaline earth metal salts, preferably alkali metal salts, in particular the sodium salt thereof.
  • the removal of methanol from the mixture is effectuated by distillation e.g. under conditions that allow to retain inert solvent in the mixture, more preferably the removal of methanol via distillation takes place at about 70 °C at ambient pressure or at lower temperatures under reduced pressure, e.g. at about 40 °C under about 350 mbar vacuum.
  • this distillation is performed until methanol is completely removed from the mixture.
  • the mixture may be cooled thereafter to about 10 °C.
  • the removal of methanol is effectuated before the addition of compound IV and/or the formylating agent.
  • the formylation reaction is completed first before methanol is removed from the mixture as described above.
  • methanol is removed after the compound III was produced and before the compound III is reacted with an alkylating agent (etherification reaction), preferably by distillation as described above.
  • catalysts can be added.
  • Suitable catalysts are phase transfer catalysts, selected from crown ethers, such as 18-brown-6, azacrown, thiacrown; ionophore; cryptand; phosphonium salts, such as tetrabutyl phosphonium chloride, tetrabutyl phosphonium bromide, benzyltrimethyl phosphonium chloride and benzyltrimethyl phosphonium bromide; or quaternary ammonium salts, such as benzyltrialkylammonium halides and benzyltrialkylammonium hydroxide and tetralkylammonium halides; preferably benzyltrialkylammonium halides, benzyltributylammonium, benzyltrimethylammonium or benzyltriethylammonium halide, particularly preferred as bromide or chloride, in particular benzyl
  • the catalyst is usually provided at very low amounts usually ranging from 0.01 to 0.5 molar eq. of compounds IV, preferably from 0.01 to 0.2 molar eq., and even more preferably from 0.01 to 0.1 molar eq..
  • the catalyst is added to the reaction mixture prior to compound IV.
  • the catalyst is added as an aq. solution.
  • the etherification reaction is performed in the presence of an inert solvent, preferably in presence of a biphasic mixture of water and water-immiscible solvents such as xylene, benzene, chlorobenzene, fluorobenzene, cumene, p-cymene or toluene, preferably toluene.
  • an inert solvent preferably in presence of a biphasic mixture of water and water-immiscible solvents such as xylene, benzene, chlorobenzene, fluorobenzene, cumene, p-cymene or toluene, preferably toluene.
  • the reaction may be carried out in a wide temperature range, typically from 0 °C to 100 °C.
  • a preferred temperature range is from 10 to 40 °C; even more preferably at ambient temperatures of about 25 °C.
  • Suitable halogenating agents are thionyl chloride, thionyl bromide, sulfinyl chloride, oxalyl chloride, phosgene, chlorine, bromine, HBr in acetic acid, HBr in water, phosphorus trichloride, phosphorus pentachloride, and phosphorous tribromide, preferably thionyl chloride or bromide, in particular thionyl chloride.
  • the halogenating agent is usually provided in excess of compounds II, preferable 0.9- 10molar equivalents; more preferably 0.9 to 6 molar eq. of compounds II; and even more preferably 2-6 molar eq..
  • the halogenation reaction is performed in the absence of an inert solvent, in particular in absence of an aromatic hydrocarbon solvent.
  • catalysts can be added to the reaction mixture, more preferably the catalyst is added after the addition of halogenating agent and compound II.
  • Suitable catalysts are /V,A/-dimethylformamide (DMF), A/-formyl morpholine, A/-formyl piperidine and pyridine, in particular DMF.
  • the catalyst is usually provided at very low amounts usually ranging from 0.01 to 0.5 molar eq. of compounds II, preferably from 0.01 to 0.2 molar eq., and even more preferably from 0.01 to 0.1 molar eq..
  • the first part of the reaction is followed by a removal of the excess halogenating agent. Even more preferably, this removal is effectuated by distillation, in particular evaporation under reduced pressure.
  • the second part of the reaction, the esterification of the acyl halide Ila with methanol is usually or preferably carried out in the presence of an inert solvent.
  • the esterification is performed in the presence of a base.
  • Suitable bases are organic bases such as tertiary amines, triethylamine, tri(n-butyl)amine, tri(n-propyl)amine, diisopropylethylamine, tetramethylenediamine, methylpiperidine, diazabicyclo[3,3,0]octane; and pyridines, piperidines; and inorganic bases such as hydroxide, carbonates or phosphate salts of Li, K, Na, Ba, Ca and Cs; preferably triethylamine and pyridine, in particular triethylamine.
  • Methanol is usually provided in excess of compound II, preferable 1.1-30 molar equivalents; more preferably 2-10 molar eq. of compounds IV; and even more preferably 2-4 molar eq..
  • the reaction can be carried out at pressure ranges typically from 0.5 atm to 2 atm, in particular at ambient pressure (0.8 to 1.5 atm).
  • reaction can be stopped by quenching by addition of water.
  • the present invention also relates to the novel compound of formula II and to the novel compound of formula I wherein X is Cl, being useful as intermediates for preparing fungicidal methyl (E)-3-methoxy- 2-[3-methyl-2-[[(E)-1-(het)arylethylideneamino]oxymethyl]phenyl]prop-2-enoates.
  • Comparative example-2 a) Synthesis of (4E)-4-(methoxymethylene)isochroman-3-one (according to CN1072667316) Solid sodium methoxide (7.29 g, 0.134 moles) and toluene (200ml) were mixed at 28-30 °C followed by dropwise addition of methyl formate (12.49 ml, 0.202 moles) in 30 min and reaction mixture was further stirred for 30 min at the same temperature. Then, 3-isochromone (10 g, 0.067 moles) added to reactor and stirred further for 12 hours.
  • Aqueous solution of tetrabutylammonium bromide (0.652 g, 0.002 moles) was then added at 30 °C followed by dropwise addition of dimethyl sulfate (12.98 ml, 0.134 moles) over 20 min.
  • Aqueous solution of potassium carbonate (3.49 g, 0.0873 moles) and further reaction was stirred at same temperature for one hour. Upon completion the reaction was added water (50 ml) was added and the toluene layer was separated. The aq. layer was re-extracted with toluene (50 ml).
  • This comparative example-3 provided lower yield of the desired product in comparison to example-1 according to the invention.
  • reaction mass was dissolved in 5 ml toluene and was dosed to reaction flask containing methanol (1.5 g, 0.048 moles) and triethylamine (0.49 g, 0.0048 moles) maintained at 0 °C over 30 mins. Then the reaction mass was quenched by addition of water at 10 °C. The toluene layer was separated and washed with brine, on evaporation of this layer obtained methyl (E)-2-[2-(chloromethyl)- 3-methyl-phenyl]-3-methoxy-prop-2-enoate (0.96g, Yield: 77%).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne des procédés permettant d'obtenir des (E)-2-[2-halométhyl)-3-méthyl-phényl]-3-hydroxy-prop-2-énoates de méthyle et des intermédiaires de ceux-ci. Ces composés sont utilisés en tant qu'intermédiaires pour la préparation de composés de type strobilurine pour la lutte contre des champignons phytopathogènes contenant une substitution d'acide aminé F129L dans la protéine cytochrome b mitochondriale (également appelée mutation F129L dans le gène du cytochrome b mitochondrial) conférant une résistance aux inhibiteurs de Qo.
PCT/EP2025/056288 2024-03-14 2025-03-07 Procédé permettant d'obtenir des (e)-2-[2-(halométhyl)-3-méthyl-phényl]-3-méthoxy-prop-2-énoates de méthyle et des intermédiaires de ceux-ci Pending WO2025190803A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN202411018456 2024-03-14
IN202411018456 2024-03-14
EP24172986.2A EP4644358A1 (fr) 2024-04-29 2024-04-29 Procédé pour obtenir des (e)-2-[2-(halométhyl)-3-méthyl-phényl-3-méthoxy-prop-2-énoates de méthyle et leurs intermédiaires
EP24172986.2 2024-04-29

Publications (1)

Publication Number Publication Date
WO2025190803A1 true WO2025190803A1 (fr) 2025-09-18

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2025/056288 Pending WO2025190803A1 (fr) 2024-03-14 2025-03-07 Procédé permettant d'obtenir des (e)-2-[2-(halométhyl)-3-méthyl-phényl]-3-méthoxy-prop-2-énoates de méthyle et des intermédiaires de ceux-ci

Country Status (1)

Country Link
WO (1) WO2025190803A1 (fr)

Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999011129A1 (fr) * 1997-09-04 1999-03-11 E.I. Du Pont De Nemours And Company Compositions enantiomeriquement enrichies et leur utilisation pesticide
US20040152894A1 (en) 2001-06-26 2004-08-05 Nippon Soda Co. Ltd Process for producing acrylic acid derivative
CN103827220A (zh) 2011-07-25 2014-05-28 沙伯基础创新塑料知识产权有限公司 阻燃聚(亚芳基醚)-聚硅氧烷嵌段共聚物组合物和制品
CN107267316A (zh) 2017-06-25 2017-10-20 南通迪松纺织品有限公司 防蚊香皂
WO2021153754A1 (fr) 2020-01-31 2021-08-05 住友化学株式会社 Procédé de lutte contre les champignons de la rouille du soja résistant aux fongicides qoi
WO2021219388A1 (fr) 2020-04-28 2021-11-04 Basf Se Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes, contenant une substitution d'acides aminés f129l dans la protéine cytochrome b mitochondrial conférant une résistance aux inhibiteurs iii de qo
WO2021219387A1 (fr) 2020-04-28 2021-11-04 Basf Se Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes contenant une substitution d'acides aminés f129l dans la protéine cytochrome b mitochondrial conférant une résistance à des inhibiteurs ii de qo
WO2021219386A1 (fr) 2020-04-28 2021-11-04 Basf Se Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes, contenant une substitution d'acides aminés f129l dans la protéine cytochrome b mitochondrial conférant une résistance aux inhibiteurs i de qo
WO2021219390A1 (fr) 2020-04-28 2021-11-04 Basf Se Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes, contenant une substitution d'acides aminés f129l dans la protéine cytochrome b mitochondrial conférant une résistance à des inhibiteurs iv de qo
WO2021249928A1 (fr) 2020-06-10 2021-12-16 Basf Se Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes, contenant une substitution d'acides aminés f129l dans la protéine cytochrome b mitochondrial conférant une résistance à des inhibiteurs de qo v
WO2022008303A1 (fr) 2020-07-08 2022-01-13 Basf Se Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes, contenant une substitution d'acides aminés f129l dans la protéine du cytochrome b mitochondrial conférant une résistance à des inhibiteurs de qo vi
WO2022013009A1 (fr) 2020-07-16 2022-01-20 Basf Se Composés de type strobilurine et leurs utilisations dans la lutte contre des champignons phytopathogènes
WO2023072670A1 (fr) 2021-10-28 2023-05-04 Basf Se Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes, contenant une substitution d'acide aminé f129l dans la protéine cytochrome b mitochondriale conférant une résistance à des inhibiteurs qo x
WO2023072671A1 (fr) 2021-10-28 2023-05-04 Basf Se Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes, contenant une substitution d'acide aminé f129l dans la protéine cytochrome b mitochondriale conférant une résistance à des inhibiteurs qo ix
WO2023072672A1 (fr) 2021-10-28 2023-05-04 Basf Se Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes, contenant une substitution d'acide aminé f129l dans la protéine cytochrome b mitochondriale conférant une résistance à des inhibiteurs qo xi
EP4242198A1 (fr) 2022-03-07 2023-09-13 Basf Se Utilisation de composés de type strobilurine pour lutter contre les champignons phytopathogènes contenant une substitution d'acide aminé f129l dans la protéine mitochondriale du cytochrome b conférant une résistance aux inhibiteurs qo iv

Patent Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999011129A1 (fr) * 1997-09-04 1999-03-11 E.I. Du Pont De Nemours And Company Compositions enantiomeriquement enrichies et leur utilisation pesticide
US20040152894A1 (en) 2001-06-26 2004-08-05 Nippon Soda Co. Ltd Process for producing acrylic acid derivative
CN103827220A (zh) 2011-07-25 2014-05-28 沙伯基础创新塑料知识产权有限公司 阻燃聚(亚芳基醚)-聚硅氧烷嵌段共聚物组合物和制品
CN107267316A (zh) 2017-06-25 2017-10-20 南通迪松纺织品有限公司 防蚊香皂
WO2021153754A1 (fr) 2020-01-31 2021-08-05 住友化学株式会社 Procédé de lutte contre les champignons de la rouille du soja résistant aux fongicides qoi
WO2021219388A1 (fr) 2020-04-28 2021-11-04 Basf Se Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes, contenant une substitution d'acides aminés f129l dans la protéine cytochrome b mitochondrial conférant une résistance aux inhibiteurs iii de qo
WO2021219387A1 (fr) 2020-04-28 2021-11-04 Basf Se Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes contenant une substitution d'acides aminés f129l dans la protéine cytochrome b mitochondrial conférant une résistance à des inhibiteurs ii de qo
WO2021219386A1 (fr) 2020-04-28 2021-11-04 Basf Se Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes, contenant une substitution d'acides aminés f129l dans la protéine cytochrome b mitochondrial conférant une résistance aux inhibiteurs i de qo
WO2021219390A1 (fr) 2020-04-28 2021-11-04 Basf Se Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes, contenant une substitution d'acides aminés f129l dans la protéine cytochrome b mitochondrial conférant une résistance à des inhibiteurs iv de qo
WO2021249928A1 (fr) 2020-06-10 2021-12-16 Basf Se Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes, contenant une substitution d'acides aminés f129l dans la protéine cytochrome b mitochondrial conférant une résistance à des inhibiteurs de qo v
WO2022008303A1 (fr) 2020-07-08 2022-01-13 Basf Se Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes, contenant une substitution d'acides aminés f129l dans la protéine du cytochrome b mitochondrial conférant une résistance à des inhibiteurs de qo vi
WO2022013009A1 (fr) 2020-07-16 2022-01-20 Basf Se Composés de type strobilurine et leurs utilisations dans la lutte contre des champignons phytopathogènes
WO2023072670A1 (fr) 2021-10-28 2023-05-04 Basf Se Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes, contenant une substitution d'acide aminé f129l dans la protéine cytochrome b mitochondriale conférant une résistance à des inhibiteurs qo x
WO2023072671A1 (fr) 2021-10-28 2023-05-04 Basf Se Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes, contenant une substitution d'acide aminé f129l dans la protéine cytochrome b mitochondriale conférant une résistance à des inhibiteurs qo ix
WO2023072672A1 (fr) 2021-10-28 2023-05-04 Basf Se Utilisation de composés de type strobilurine pour lutter contre des champignons phytopathogènes, contenant une substitution d'acide aminé f129l dans la protéine cytochrome b mitochondriale conférant une résistance à des inhibiteurs qo xi
EP4242198A1 (fr) 2022-03-07 2023-09-13 Basf Se Utilisation de composés de type strobilurine pour lutter contre les champignons phytopathogènes contenant une substitution d'acide aminé f129l dans la protéine mitochondriale du cytochrome b conférant une résistance aux inhibiteurs qo iv

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
"Processes to obtain methyl (2E)-2-[2-(halomethyl)-3-methyl-phenyl]-2-methoxyimino-acetates, methyl (E)-2-[2-(halomethyl)-3-methyl-phenyl]-3-methoxy-prop-2-enoates and intermediates thereof ED - Darl Kuhn", IP.COM, IP.COM INC., WEST HENRIETTA, NY, US, 27 March 2024 (2024-03-27), XP013197338, ISSN: 1533-0001 *

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