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Avermectin B1 derivatives having an aminosulfonyloxy substituent in the 4′-position

  • US 6,933,260 B2
  • Filed: 12/20/2002
  • Issued: 08/23/2005
  • Est. Priority Date: 12/21/2001
  • Status: Expired due to Term
First Claim
Patent Images

1. A compound of formula:

  • embedded imagewherein the bond marked by custom character indicates the S- as well as the R-isomer at the 4″

    -position; and

    whereinR1 is C1-C12alkyl, C3-C8cycloalkyl;

    or C2-C12alkenyl;

    R2 is hydrogen, unsubstituted or mono- to penta-substituted C1-C12alkyl or unsubstituted or mono- to penta-substituted C2-C12alkenyl;

    unsubstituted or mono- to penta-substituted C2-C12alkynyl;



    C(O)R4 or SO2R4;

    R3 is hydrogen, C1-C12alkyl, mono- to penta-substituted C1-C12alkyl, unsubstituted or mono- to penta-substituted C3-C12cycloalkyl, unsubstituted or mono- to penta-substituted C2-C12alkenyl;

    or unsubstituted or mono- to penta-substituted C2-C12alkynyl;

    or R2 and R3 together are a three- to seven-membered alkylene bridge or a four- to seven-membered alkenylene bridge wherein one CH2 group in the alkylene or alkenylene may have been replaced by O, S or NR5;

    or are a group ═

    N+

    N

    , and wherein the substituents of the alkyl, alkenyl, alkynyl, alkylene, alkenylene and cycloalkyl radicals defined under R2 and R3 are selected from the group consisting of OH, halogen, halo-C1-C2alkyl, CN, NO2, C2-C6alkynyl;

    C3-C8cycloalkyl unsubstituted or substituted by from one to three methyl groups, norbornylenyl;

    C3-C8cycloalkenyl unsubstituted or substituted by from one to three methyl groups;

    C3-C8halocycloalkyl, C1-C12alkoxy, C1-C6alkoxy-C1-C6alkyl, C1-C6alkoxy-C1-C6alkoxy-C1-C6alkyl, C3-C8cycloalkoxy, C1-C12haloalkoxy, C1-C12alkylthio, C3-C8cycloalkylthio, C1-C12haloalkylthio, C1-C12alkylsulfinyl, C3-C8cycloalkylsulfinyl, C1-C12haloalkylsulfinyl, C3-C8halocycloalkylsulfinyl, C1-C12alkylsulfonyl, C3-C8cycloalkylsulfonyl, C1-C12haloalkylsulfonyl, C3-C8halocycloalkylsulfonyl, C2-C8alkenyl, C2-C8alkynyl, NH(C1-C6alkyl), N(C1-C6alkyl)2, —

    C(═

    O)R4, —

    NHC(═

    O)R7, —

    P(═

    O)(OC1-C6alkyl)2;

    aryl, heterocyclyl, aryloxy, heterocyclyloxy;

    aryl, heterocyclyl, aryloxy, heterocyclyloxy that, depending upon the possibilities of substitution at the ring, are mono- to penta-substituted by substituents selected from the group consisting of OH, halogen, CN, NO2, C1-C12alkyl, C3-C8cycloalkyl, C1-C12haloalkyl, C1-C12alkoxy, C1-C12haloalkoxy, C1-C12alkylthio, C1-C12haloalkylthio, C1-C6alkoxy-C1-C6alkyl, dimethylamino-C1-C6alkoxy, C2-C8alkenyl, C2-C8alkynyl, phenoxy, phenyl-C1-C6alkyl;

    phenoxy unsubstituted or substituted by from one to three substituents selected independently of one another from halogen, methoxy, trifluoromethyl and trifluoromethoxy;

    phenyl-C1-C6alkoxy unsubstituted or substituted in the aromatic ring by from one to three substituents selected independently of one another from halogen, methoxy, trifluoromethyl and trifluoromethoxy;

    phenyl-C2-C6alkenyl, phenyl-C2-C6alkynyl, methylenedioxy, —

    C(═

    O)R4, —

    O—

    C(═

    O)R7, —

    NH—

    C(═

    O)R7, NH2, NH(C1-C12alkyl), N(C1-C12alkyl)2, C1-C6alkylsulfinyl, C3-C8cycloalkylsulfinyl, C1-C6haloalkylsulfinyl, C3-C8halocycloalkylsulfinyl, C1-C6alkylsulfonyl, C3-C8cycloalkylsulfonyl, C1-C6haloalkylsulfonyl and C3-C8halocycloalkylsulfonyl;

    R4 is H, OH, C1-C8alkyl, C1-C8alkyl mono- to hepta-substituted by halogen, nitro, C1-C8alkoxy, OH, SH, NH2, NH(C1-C12alkyl) or N(C1-C12alkyl)2;

    C1-C8alkoxy, halo-C1-C8alkoxy, C3-C8cycloalkyl, C3-C8cycloalkoxy, C2-C8alkenyl, C2-C8alkenyloxy, C2-C8alkynyl, C2-C8alkynyloxy, NH2, NH(C1-C12alkyl), N(C1-C12alkyl)2, aryl, aryloxy, benzyl, benzyloxy, heterocyclyl, heterocyclyloxy, heterocyclylmethyl or heterocyclylmethoxy;

    wherein the radicals aryl, aryloxy, benzyl, benzyloxy, heterocyclyl, heterocyclyloxy, heterocyclylmethyl and heterocyclylmethoxy are unsubstituted or, depending upon the possibilities of substitution at the ring, are substituted by from one to three substituents selected independently of one another from halogen, C1-C12alkyl, C1-C12haloalkyl, C1-C12alkoxy, C1-C12haloalkoxy, C1-C6alkoxy-C1-C6alkoxy, C1-C12alkylthio, C1-C12haloalkylthio, C2-C8alkenyloxy, C2-C8alkynyloxy, nitro and cyano;

    R5 is C1-C8alkyl, C3-C8cycloalkyl, C2-C8alkenyl, C2-C8alkynyl, benzyl or —

    C(═

    O)—

    R6;

    R6 is H, OH, SH, NH2, NH(C1-C12alkyl), N(C1-C12alkyl)2, C1-C12alkyl, C1-C12haloalkyl, C1-C12alkoxy, C1-C12haloalkoxy, C1-C6alkoxy-C1-C6alkoxy, C1-C12alkylthio, C2-C8alkenyloxy, C2-C8alkynyloxy;

    phenyl, phenoxy, benzyloxy, NH-phenyl, N(C1-C6alkyl)-phenyl, NH—

    C1-C6alkyl-C(═

    O)—

    R8, N(C1-C6alkyl)-C1-C6alkyl-C(═

    O)—

    R8;

    or phenyl, phenoxy, benzyloxy, NH-phenyl or N(C1-C6alkyl)-phenyl each of which is substituted in the aromatic ring by from one to three substituents selected independently of one another from halogen, C1-C6alkoxy, C1-C6haloalkyl and C1-C6haloalkoxy;

    R7 is H, C1-C12alkyl, C1-C12haloalkyl, C2-C8alkenyl, C2-C8alkynyl, phenyl, benzyl, NH2, NH(C1-C12alkyl), N(C1-C12alkyl)2, NH-phenyl or N(C1-C12alkyl)-phenyl; and

    R8 is H, OH, C1-C12alkyl, C1-C12alkoxy, C1-C6alkoxy-C1-C6alkoxy, C2-C8alkenyloxy, phenyl, phenoxy, benzyloxy, NH2, NH(C1-C12alkyl), N(C1-C12alkyl)2, NH-phenyl or N(C1-C12alkyl)-phenyl;

    or, where applicable, an E/Z isomer, a mixture of E/Z isomers and/or a tautomer, in each case in free form or in salt form.

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