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Process and a composition for immunizing plants against diseases

  • US 4,931,581 A
  • Filed: 08/18/1988
  • Issued: 06/05/1990
  • Est. Priority Date: 08/21/1987
  • Status: Expired due to Term
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First Claim
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1. Compounds of formula XI'"'"' ##STR113## in which:

  • X'"'"' is hydrogen, halogen, methyl, methoxy or COOH;

    Eb hydrogen, C1 -C16 alkyl, benzyl, acetyl, the sulfonic acid radical (--SO3 H--), cyano, or as part of a disulfide bridge, is a second radical ##STR114## in which;

    Zb is cyano or COA;

    A is UR, N(R1)R2 or U1 N(═

    C)n (R3)R4 ;

    M is the molar equivalent of an alkali metal or alkaline earth metal ion that has been formed from a corresponding base or basic compound;

    U is oxygen or sulfur;

    U1 is oxygen or --N(R5)--;

    R is C1 -C8 alkyl, C1 -C8 alkyl that is substituted by halogen, cyano, hydroxy or by U--C1 -C3 alkyl, (T)--COOH or (T)--COOC1 -C4 alkyl, C3 -C6 alkenyl, halo-substituted C3 -C6 alkenyl, C3 -C6 alkynyl, halo-substituted C3 -C6 -alkynyl, (T)n --C3 -C8 cycloalkyl, or a group selected from the following;

    ##STR115## each of Xa, Xb and Xc, independently of the others, is hydrogen, halogen, hydroxy, cyano, HOOC, MOOC, C1 -C3 alkyl-OOC, C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C2 haloalkyl having up to 5 halogen atoms;

    orXa is C1 -C2 haloalkoxy having up to 5 halogen atoms, phenyl, phenoxy, benzyloxy or sulfamoyloxy and Xb and Xc are both hydrogen;

    orXa is phenyl, phenoxy or benzyloxy and Xb is halogen or methyl and Xc is hydrogen;

    orXa, Xb and Xc together are 4 or 5 fluorine atoms;

    naphth is a naphthyl radical that is unsubstituted or is substituted by halogen, methyl or by methoxy;

    W is a 5- to 7-membered saturated or unsaturated heterocycle having from 1 to 3 hetero atoms from the group O, N and S that is unsubstituted or is substituted by halogen, trifluoromethyl, cyano, C1 -C2 alkyl or by a C1 -C2 -alkoxycarbonyl-C2 -C4 alkyleneimino radical, or is a monosaccharide radical;

    T is a bridge member --CH2 --, --CH2 CH2 --, --CH(CH3)--, --CH2 CH2 CH2 -- or --CH2 CH2 O--;

    R1 is C1 -C5 alkyl, C1 -C5 alkyl interrupted by an oxygen or sulfur atom, C1 -C5 alkyl substituted by halogen, cyano, HOOC or by C1 -C2 alkyl-OOC, C1 -C5 alkyl interrupted by an oxygen or sulfur atom and substituted by halogen, cyano, HOOC or by C1 -C2 alkyl-OOC, C3 -C5 alkenyl, C3 -C5 -alkenyl substituted by C1 -C3 alkyl-OOC, C3 -C5 alkynyl, C3 -C5 -alkynyl substituted by C1 -C3 alkyl-OOC, (T)n --C3 -C6 cycloalkyl, (T)n --C3 -C6 cycloalkyl substituted by C1 -C3 alkyl-OOC, (T)n -phenyl, or (T)n -phenyl substituted in the phenyl moiety by halogen, hydroxy, methyl, CF3, cyano, methoxy, HOOC or by MOOC;

    R2 is hydroxy, C1 -C3 alkyl, C1 -C3 alkyl substituted by cyano or by C1 -C3 -alkoxy, C1 -C4 alkoxy, or a 3- to 6-membered saturated or unsaturated heterocycle containing O, N or S as hetero atoms;

    R1 and R2 together are a heterocycle W;

    R3 is hydrogen, cyano, C1 -C6 alkyl, phenyl, phenyl substituted by halogen, hydroxy, methyl, methoxy, HOOC or by MOOC, or a heterocycle W;

    R4 is C1 -C6 alkyl, C1 -C6 alkanoyl, C1 -C3 alkanoyl substituted by halogen or by C1 -C3 alkoxy, C3 -C5 alkenoyl, or C3 -C5 alkenoyl substituted by halogen or by C1 -C3 alkoxy;

    R3 and R4 together are a heterocycle W or a carbocyclic ring W'"'"';

    W'"'"' is a carbocyclic radical having from 3 to 7 ring carbon atoms;

    R5 is methyl;

    R6 is hydrogen or C1 -C4 alkyl; and

    n is 0 or 1.

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