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    PROCESS AND INTERMEDIATES FOR THE PREPARATION OF PYROXASULFONE AND FENOXASULFONE
    3.
    发明公开
    PROCESS AND INTERMEDIATES FOR THE PREPARATION OF PYROXASULFONE AND FENOXASULFONE 审中-公开

    公开(公告)号：EP4177244A3

    公开(公告)日：2023-08-09

    申请号：EP22198307.5

    申请日：2020-07-10

    申请人： Adama Agan Ltd.

    发明人： Barda, Barda ,  Papo, Nitsan ,  Recsei, Carl

    IPC分类号： C07D261/04 ,  C07C41/22 ,  C07C43/225 ,  C07D231/20 ,  C07D413/12

    摘要： The invention relates to a process for preparing immediate precursors for pyroxasulfone and fenoxasulfone preparation of the formula (I). The process comprises a bromination reaction of a benzylic position without light irradiation (step a), followed by thoination reaction, which substitutes the bromine atom (step b) and after the protecting group is removed, and the revealed thiol or thiolate reacts with a substituted isoxazoline bearing a leaving group at the 3-position (step c).

    wherein
    Y = protecting group
    In another variant of the invention the pyroxasulfone or fenoxasulfone immediate precursor is synthesized from the arylmethyl bromide by first forming a carbon-sulfur bond at the 3-position of a 2-isoxazoline through displacement of a leaving group at the 3-position (particularly acid derived residues such as phosphoryl, sulfanyl, halo, cyano or carboxyl groups) by an appropriate thionating reagent. The resulting adducts, which is a S-protected 3-thio-2-isoxazoline, may be treated with base to remove the protecting group, to reveal a thiol or thiolate which may subsequently react with the arylmethyl bromide to form the Pyroxasulfone or Fenoxasulfone immediate precursor.

    Ar = aryl, Y = protecting group and X = leaving group

    PROCESS AND INTERMEDIATES FOR THE PREPARATION OF PYROXASULFONE, FENOXASULFONE AND VARIOUS SULFONE ANALOGS OF 5,5-DIMETHYL-4H-1,2-OXAZOLE
    4.
    发明公开
    PROCESS AND INTERMEDIATES FOR THE PREPARATION OF PYROXASULFONE, FENOXASULFONE AND VARIOUS SULFONE ANALOGS OF 5,5-DIMETHYL-4H-1,2-OXAZOLE 审中-公开

    公开(公告)号：EP4177252A2

    公开(公告)日：2023-05-10

    申请号：EP22198312.5

    申请日：2020-07-10

    申请人： Adama Agan Ltd.

    发明人： Barda, Yaniv ,  Papo, Nitsan ,  Recsei, Carl

    IPC分类号： C07D413/12 ,  C07D231/20 ,  C07D261/04 ,  C07C43/225

    摘要： The invention relates to a process for preparing immediate precursors for pyroxasulfone and fenoxasulfone of the formula (I) and (I').


    The pyroxasulfone or fenoxasulfone immediate precursor is synthesized from the arylmethyl bromide by first forming a carbon-sulfur bond at the 3-position of a 2-isoxazoline through displacement of a leaving group at the 3-position (particularly acid derived residues such as phosphoryl, sulfanyl, halo, cyano or carboxyl groups) by an appropriate thionating reagent. The resulting adducts, which is a S-protected 3-thio-2-isoxazoline, may be treated with base to remove the protecting group, to reveal a thiol or thiolate which may subsequently react with the arylmethyl bromide to form the Pyroxasulfone or Fenoxasulfone immediate precursor.