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WO2015123228A1 - Procédés pour la synthèse d'intermédiaires de l'herbicide flucetosulfuron - Google Patents

Procédés pour la synthèse d'intermédiaires de l'herbicide flucetosulfuron Download PDF

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Publication number
WO2015123228A1
WO2015123228A1 PCT/US2015/015302 US2015015302W WO2015123228A1 WO 2015123228 A1 WO2015123228 A1 WO 2015123228A1 US 2015015302 W US2015015302 W US 2015015302W WO 2015123228 A1 WO2015123228 A1 WO 2015123228A1
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compound
comp
group
reacting
solvent
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PCT/US2015/015302
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English (en)
Inventor
Wangge SHOU
Jianguo Chen
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FMC Corp
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FMC Corp
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Priority to KR1020167021838A priority Critical patent/KR20160119782A/ko
Priority to JP2016551314A priority patent/JP2017506634A/ja
Publication of WO2015123228A1 publication Critical patent/WO2015123228A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C07D213/71—Sulfur atoms to which a second hetero atom is attached
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3

Definitions

  • the present invention relates to the synthesis of intermediates of flucetosulfuron, a sulfonyl urea herbicide, and the intermediates created as a result of the synthesis.
  • BACKGROUND Sulfonylureas are a family of environmentally compatible herbicides that were discovered in 1975 and first commercialized for wheat and barley crops in 1982. They have now been developed and commercialized worldwide in all major agronomic crops and for many specialty uses (e.g., rangeland/pasture, forestry, vegetation management).
  • Sulfonylureas represent a major advance in global crop protection technology and have revolutionized weed control by introducing a unique mode of action. Specifically, these compounds interfere with a key enzyme required for weed cell growth— acetolactate synthase.
  • sulfonylureas are compatible with the global trend toward post emergence weed control and integrated pest management.
  • Sulfonylurea herbicides kill weeds by inhibiting the enzyme acetolactate synthase, which is essential to their growth. They work on a broad range of grasses and broadleaf weeds, but not on crops they are designed to protect. Crops like rice, wheat, barley, soybean, maize, and many others are able to metabolize sulfonylureas safely.
  • Flucetosulfuron is a specific sulfonylurea herbicide used to protect wheat, barley, grass and rice from weeds. Although some methods for the synthesis of flucetosulfuron are known, there is a need in the art for more economical processes for the synthesis of production intermediates for flucetosulfuron that produce a high yield of the intermediates.
  • the present document discloses processes for the synthesis of intermediates for a sulfonyl urea derivative (Flucetosulfuron) using 3-chloro-2-cyanopyridine (compound 1) as a starting material through multiple steps.
  • the present disclosure also provides novel intermediate compounds prepared from the disclosed processes.
  • Comp-2 a compound of 3-(benzylthio) pyridine-2-carbonitrile, hereinafter also referred to as "Comp-2”, of the following formula:
  • Comp-2 is provided.
  • the present disclosure provides a process for preparing Comp-2 that includes the step of reacting 3-chloro-2-cyanopyridine with benzyl mercaptan in a solvent in the presence of a base.
  • the solvent is selected from toluene, chlorobenzene, and xylene.
  • the base is selected from aqueous sodium hydroxide, sodium hydroxide flakes, aqueous potassium hydroxide, and potassium hydroxide flakes.
  • the base is aqueous sodium hydroxide.
  • the solvent is toluene.
  • the present disclosure provides a process for preparing
  • Comp-3 l-(3-(benzylthio)pyridine-2-yl)propan-l-one, hereinafter also referred to as "Comp-3", that includes the step of adding Comp-2 to a solution that includes ethyl magnesium bromide in a solvent and reacting Comp-2 with ethyl magnesium bromide at a reaction temperature ranging from about -20° C to about 10° C.
  • the solvent is selected from
  • THF tetrahydrofuran
  • methyl tert-butyl ether methyl tert-butyl ether
  • toluene 2-methyltetrahydrofuran
  • the present disclosure provides a process for preparing
  • Comp-3 that includes the steps of adding ethyl magnesium bromide to a solution that includes Comp-2 in a solvent and reacting Comp-2 with ethyl magnesium bromide at a reaction temperature ranging from about -20° C to about 10° C.
  • the solvent is selected from tetrahydrofuran (THF), methyl tert-butyl ether, toluene, and 2- methyltetrahydrofuran.
  • the solvent is tetrahydrofuran (THF).
  • the reaction temperature ranges from about 0° C to about 5° C.
  • the present disclosure provides a compound of l-(3-(benzylthio) pyridin-2-yl)-2-fluoropropan-l-ol, hereinafter also referred to as "Comp-6”, with the following formula:
  • the present disclosure provides a process for preparing a
  • the solvent is selected from 1, 2-dichloroethane, methyl tert- butyl ether, tetrahydrofuran (THF), chlorobenzene, methanol, isopropanol, and ethanol.
  • the solvent is methanol.
  • the present disclosure provides a compound of
  • the present disclosure provides a process for preparing a diasteroisomer mixture of Comp-7 that includes the step of reacting Comp-6 with 2-methoxyacetyl chloride in a solvent in the presence of a base at a reaction temperature ranging from about 0° C to about 50° C.
  • the solvent is selected from 1 , 2-dichloroethane, chlorobenzene, tetrahydrofuran (THF), and ethyl acetate.
  • the base is an organic base.
  • the organic base is selected from triethylamine, and pyridine.
  • the base is an inorganic base.
  • the inorganic base is selected from NaOH, KOH, Na 2 C0 3 and K 2 C0 3 .
  • the reaction temperature ranges from about 10° C to about 25° C.
  • the reacting step is performed in the presence of at least one catalyst.
  • the catalyst is a phase transfer catalyst.
  • the phase transfer catalyst is selected from tetra butyl ammonium chloride (TBAC), tetra butyl ammonium bromide (TBAB), aliquat- 336, and benzyltriethylammonium chloride.
  • the present disclosure provides a compound of l-(3- (chlorosulfonyl)pyridin-2-yl)-2-fluoropropyl-2-methoxyacetate, hereinafter also referred to an "Comp-8", with the following formula:
  • the present disclosure provides a process for preparing Comp-8 that includes the step of reacting Comp-7 with a chlorination agent in a solvent in the presence of an organic acid at a reaction temperature ranging from about -15° C to about 20° C.
  • the solvent is selected from 1 ,2-dichloroethane ("DCE”), dichloromethane
  • the chlorination agent is selected from chlorine and sulfuryl chloride.
  • the organic acid is selected from aqueous formic acid and aqueous acetic acid.
  • the present disclosure provides a process for preparing a
  • Comp-9 that includes the step of reacting Comp-8 with ammonia gas in a solvent at a reaction
  • the solvent is selected from 1 ,2-dichloroethane (DCE), dichloromethane (DCM), ethyl acetate, and
  • the present disclosure provides processes for the synthesis of intermediates of a sulfonyl urea derivative (flucetosulfuron) using 3-chloro-2-cyanopyridine as a starting material.
  • the entire synthetic route from 3-chloro-2-cyanopyridine to flucetosulfuron is shown in the following scheme:
  • organic base includes, without limitation, amine compounds (e.g., primary, secondary and tertiary amines), heterocycles including nitrogen-containing heterocycles, and ammonium hydroxide.
  • inorganic base includes, without limitation, inorganic compounds with the ability to react with, or neutralize, acids to form salts, such as, for example, metal salts of hydroxide, carbonate, bicarbonate and phosphate.
  • chlorination agent includes, without limitation, halogens and inorganic compounds, such as, for example, chlorine and sulfuryl chloride.
  • phase transfer catalyst includes compounds that facilitate the migration of a reactant from one phase into another phase where a reaction occurs.
  • Phase transfer catalysis refers to the acceleration of the reaction upon the addition of the phase transfer catalyst.
  • the present disclosure provides a compound of Comp-2, of the following formula:
  • the present disclosure provides a process for preparing Comp-2, illustrated by the following scheme:
  • This aspect includes reacting Comp-1 with benzyl mercaptan in a solvent in the presence of a base.
  • the solvent is selected from toluene, chlorobenzene, and xylene.
  • the base is selected from aqueous sodium hydroxide, sodium hydroxide flakes, aqueous potassium hydroxide, and potassium hydroxide flakes.
  • the base is aqueous sodium hydroxide.
  • the solvent is toluene.
  • the present disclosure provides a process for preparing Comp-3, illustrated by the followin scheme:
  • This aspect includes adding Comp-2 to a solution that includes ethyl magnesium bromide in a solvent and reacting Comp-2 with ethyl magnesium bromide at a reaction temperature ranging from about -20° C to about 10° C.
  • the solvent is selected from
  • THF tetrahydrofuran
  • methyl tert-butyl ether methyl tert-butyl ether
  • toluene 2-methyltetrahydrofuran
  • the present disclosure provides a process for preparing
  • l-(3-(benzylthio)pyridine-2-yl)propan-l-one that includes the steps of adding ethyl magnesium bromide to a solution that includes Comp-2 in a solvent and reacting Comp-2 with ethyl magnesium bromide at a reaction temperature ranging from about -20° C to about 10° C.
  • the solvent is selected from tetrahydrofuran, methyl tert-butyl ether, toluene, and 2- methyltetrahydrofuran.
  • the solvent is tetrahydrofuran (THF).
  • the reaction temperature ranges from about 0° C to about 5° C.
  • the present disclosure provides a compound of Comp-6, with the following formula:
  • the present disclosure provides a process for preparing
  • This aspect includes reacting Comp-5 with sodium borohydride in a solvent at a reaction temperature ranging from about -5° C to about 40° C.
  • the solvent is selected from 1 ,2-dichloroethane (DCE), methyl tert-butyl ether, tetrahydrofuran (THF), chlorobenzene, methanol, isopropanol, and ethanol.
  • the solvent is methanol.
  • the present disclosure provides a process for preparing a diasteroisomer mixture of Comp-7, illustrated b the following scheme:
  • This aspect includes reacting Comp-6 with 2-methoxyacetyl chloride in a solvent in the presence of a base at a reaction temperature ranging from about 0° C to about 50° C.
  • the solvent is selected from 1 ,2-dichloroethane (DCE), chlorobenzene, tetrahydrofuran (THF), and ethyl acetate.
  • the base is an organic base.
  • the organic base is selected from triethylamine, and pyridine.
  • the base is an inorganic base.
  • the inorganic base is selected from NaOH, KOH, Na 2 C0 3 and K 2 C0 3 .
  • the reaction temperature ranges from about 10° C to about 25° C.
  • the reacting step is performed in the presence of at least one catalyst.
  • the catalyst is a phase transfer catalyst.
  • the phase transfer catalyst is selected from TBAC, TBAB, aliquat 336, and benzyltriethylammonium chloride.
  • the present disclosure provides a process for preparing Comp-8, illustrated by the following scheme:
  • This aspect includes reacting Comp-7 with a chlorination agent in a solvent in the presence of an organic acid at a reaction temperature ranging from about -15° C to about 20° C.
  • the solvent is selected from DCE, DCM, and chlorobenzene.
  • the chlorination agent is selected from chlorine, and sulfuryl chloride.
  • the organic acid is selected from aqueous formic acid and aqueous acetic acid.
  • the present disclosure provides a process for preparing a
  • the solvent is selected from DCE, DCM, ethyl acetate, and chlorobenzene.
  • compositions and methods of the present invention are further illustrated by the following examples. These examples serve merely to illustrate particular embodiments of the invention and are not intended to limit the scope of the invention in any way. Further modifications encompassed by the disclosed invention will be apparent to those skilled in the art. All such modifications are deemed to be within the scope of the invention as defined in the present specification and claims.
  • Comp-3 (25.7g) and 95%> ethanol (75g) were charged to the flask and the agitator began to agitate while the temperature was warmed to 20-30 C°. 56g CuBr 2 was added into the above solution. The mixture was stirred at 20-30°C for 16-20 hours to complete the reaction. After the completion of the reaction, the organic solution was filtered. Next, ethanol was removed from the filtrate under reduced pressure, and DCM was added to the residue, and washed by water, 10% NaHC0 3 solution, and again by water. After phase separation, 28.6g of Comp-4 was obtained by removing DCM under reduced pressure and drying. This reaction was repeated to provide additional quantities of Comp-4.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pyridine Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Procédés de préparation de produits intermédiaires de flucetosulfuron, un herbicide sulfonylurée, sont décrits. Composés intermédiaires sont également présentés.
PCT/US2015/015302 2014-02-11 2015-02-11 Procédés pour la synthèse d'intermédiaires de l'herbicide flucetosulfuron Ceased WO2015123228A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
KR1020167021838A KR20160119782A (ko) 2014-02-11 2015-02-11 제초제 플루세토설푸론의 중간체의 합성 방법
JP2016551314A JP2017506634A (ja) 2014-02-11 2015-02-11 フルセトスルフロン除草剤の中間体を合成するためのプロセス

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201410052305.7A CN104829524A (zh) 2014-02-11 2014-02-11 除草剂氟吡磺隆的中间体的合成方法
CN201410052305.7 2014-02-11

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WO2015123228A1 true WO2015123228A1 (fr) 2015-08-20

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JP (1) JP2017506634A (fr)
KR (1) KR20160119782A (fr)
CN (1) CN104829524A (fr)
PH (1) PH12015000050A1 (fr)
WO (1) WO2015123228A1 (fr)

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CN106397311A (zh) * 2016-08-31 2017-02-15 安徽省鸿鑫生物科技有限公司 一种1‑[5‑(苯基甲氧基)‑2‑吡啶]‑乙酮的制备方法

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JP2003335758A (ja) * 2002-05-20 2003-11-28 Lg Chem Investment Ltd ピリジン誘導体、その製造方法、及び除草剤中間体としての用途

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JP2003335758A (ja) * 2002-05-20 2003-11-28 Lg Chem Investment Ltd ピリジン誘導体、その製造方法、及び除草剤中間体としての用途

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JP2017506634A (ja) 2017-03-09
KR20160119782A (ko) 2016-10-14
CN104829524A (zh) 2015-08-12
PH12015000050A1 (en) 2016-08-15

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