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Fungicides for the control of take-all disease of plants

  • US 6,248,894 B1
  • Filed: 09/28/1998
  • Issued: 06/19/2001
  • Est. Priority Date: 10/18/1991
  • Status: Expired due to Fees
First Claim
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1. A method of controlling disease in a plant caused by Gaeumannomyces sp. comprising applying to the plant locus a fungicidally effective amount of a fungicide of the formula:

  • wherein A is selected from the group consisting of —

    C(X)-amine, wherein the amine is substituted with a first and a second amine substituent or with an alkylaminocarbonyl and a hydrogen;



    C(O)—

    SR3, —

    NH—

    C(X)R4, and —

    C(═

    NR3)—

    XR7;

    the first amine substituent is selected from the group consisting of C1-C10 straight or branched alkyl, alkenyl, or alkynyl groups or mixtures thereof optionally substituted with one or more halogen, hydroxy, alkoxy, alkylthio, nitrile, alkylsulfonate, haloalkylsulfonate, phenyl, a 5-membered heteroaryl, C3-C6 cycloalkyl and C5-C6 cycloalkenyl;

    phenyl optionally substituted with one or more C1-C4 straight or branched alkyl, alkenyl, or alkynyl groups or mixtures thereof, cycloalkyl, cycloalkenyl, haloalkyl, alkoxy and nitro;

    C3-C6 cycloalkyl, C5-C6 cycloalkenyl, alkoxy, alkenoxy, alkynoxy, dialkylamino, and alkylthio;

    and the second amine substituent is selected from the group consisting of hydrogen, C1-C6 straight or branched alkyl, alkenyl, or alkynyl groups or mixtures thereof optionally substituted with one or more halogen;

    hydroxy, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, and dialkyl-phosphonyl;

    B is —

    Wm

    Q(R2)3 or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R4;

    Q is C, Si, Ge, or Sn;

    W is —

    C(R3)pH(2−

    p)


    ;

    or when Q is C, W is selected from —

    C(R3)pH(2−

    p)


    , —

    N(R3)mH(1−

    m)


    , —

    S(O)p

    , and —

    O—

    ;

    X is 0 or S;

    n is 0, 1, 2 or 3;

    m is 0 or 1;

    p is 0, 1, or 2;

    each R2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and phenyl, each optionally substituted with R4 or halogen; and

    wherein, when Q is C, R2 is selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl alkoxy, alkyloxy, alkylthio, alkylamino, dialkylamino and phenyl, each optionally substituted with R4 or halogen;

    or, wherein two R2 groups as defined above are combined to form a cyclo group with Q;

    R3 is C1-C4 alkyl;

    R4 is C1-C4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; and

    R7 is C1-C4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R4;

    or an agronomic salt forming cation;

    R is 0, 1, 2 or 3 and each R is independently selected from a) formyl, amino, trimethylsilyl, and hydroxy;

    b) C1-C4 alkyl, alkenyl, alkynyl, C3-C6 cycloalkyl, and cycloalkenyl, each optionally substituted with halo, hydroxy, thio, amino, nitro, cyano, formyl, phenyl, C1-C4 alkoxy, alkylcarbonyl, alkylthio, alkylamino, dialkylamino, alkoxycarbonyl, (alkylthio)carbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsufinyl, or alkylsulfonyl;

    c) phenyl, furyl, thienyl, pyrrolyl, each optionally substituted with halo, formyl, cyano, amino, nitro, C1-C4 alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylamino, dialkylamino, haloalkyl, and haloalkenyl;

    or d) C1-C4 alkoxy, alkenoxy, alkynoxy, C3-C6 cycloalkyloxy, cycloalkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, (alkylthio)carbonyl, phenylcarbonylamino, phenylamino, each optionally substituted with halo; and

    wherein two R groups optionally combine to form a fused benzene ring with the pyrrole ring.

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