Nova Patents
EP1493733A2

Fungicidal heterocyclic aromatic amides, their compositions and methods of use

Abstract

The present invention relates to the field of fungicidal compositions and methods. More particularly, the present invention concerns novel fungicidal heterocyclic aromatic amides of following formula I: wherein: represents a 5 membered heterocyclic aromatic ring, and methods involving application of fungicidally effective amounts of such compounds to the locus of a plant pathogen. The present invention also concerns methods useful in the preparation of heterocyclic aromatic amides and their fungicidal compositions.

EP1493733A2, drawing sheet 1
Sheet 1 of 177

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Projected expiry passed 4 August 2020, 6.1 years ago.

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10 claims: 5 independent, 5 dependent

  1. 1
    A compound of Formula I:wherein: a) represents a 5 membered heterocyclic aromatic ring in which (i) each of X1-X4 is independently O, S, NR', N, CR" or a bond;(ii) one of X1-X4 is O, S or NR';(iii) no more than one of X1-X4 is a bond;(iv) when any one of X1-X4 is S, O or NR', one of the adjacent X1-X4 must represent a bond;and(v) at least one of X1-X4 must be O, S, NR' or N;wherein R' is H, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, hydroxy, acyloxy, C1-C6 alkoxymethyl, CHF2, cyclopropyl or C1-C4 alkoxy;and, R" is independently H, halogen, cyano, hydroxy, C1-C3 alkyl, C1-C3 haloalkyl, cyclopropyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, aryl, C1-C3 NHC(O)alkyl, NHC(O)H, C1-C3 haloalkylthio, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl or nitro wherein adjacent R" substituents may form a ring or adjacent R' and R" substituents may form a ring;b) Z is O, S or NORz in which Rz is H or C1-C3 alkyl;andc) A represents (i) C3-C14 cycloalkyl, containing 0-3 heteroatoms and 0-2 unsaturations, which may be unsubstituted or substituted with halogen, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl, cyano, nitro, aroyl, aryloxy, heteroaryloxy, C1-C6 alkylthio, arylthio, heteroarylthio, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C8 acyloxy, aryl, heteroaryl, C1-C6 acyl, carboaryloxy, carboheteroaryloxy, C1-C6 carboalkoxy or amido unsubstituted or substituted with one or two C1-C6 alkyl groups,(ii) C6-C14 bi- or tricyclic ring system, containing 0-3 heteroatoms and 0-2 unsaturations, which may be unsubstituted or substituted with halogen, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl, cyano, nitro, aroyl, aryloxy, heteroaryloxy, C1-C6 alkylthio, arylthio, heteroarylthio, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C8 acyloxy, aryl, heteroaryl, C1-C6 acyl, carboaryloxy, carboheteroaryloxy, C1-C6 carboalkoxy or amido unsubstituted or substituted with one or two C1-C6 alkyl groups,(iii) aryl or heteroaryl, which may be unsubstituted or substituted with nitro, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, aryl, heteroaryl, halogen, hydroxy, C1-C6 alkoxy, C1-C6 haloalkoxy, carboaryloxy, carboheteroaryloxy, C1-C6 carboalkoxy or amido unsubstituted or substituted with one or two C1-C6 alkyl groups, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkylsulfinyl, C1-C6 OC(O)alkyl, OC(O)aryl, C3-C6 OC(O)cycloalkyl, C1-C6 NHC(O)alkyl, C3-C6 NHC(O)cycloalkyl, NHC(O)aryl, NHC(O)heteroaryl, C3-C6 cycloalkylthio, C3-C6 cycloalkylsulfonyl, C3-C6 cycloalkylsulfinyl, aryloxy, heteroaryloxy, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, arylthio, arylsulfinyl, arylsulfonyl, C(O)RY, C(NORX)RY, in which any alkyl or cycloalkyl containing substituent may be substituted with one or more halogens and in which any aryl or heteroaryl containing substituent may also be unsubstituted or substituted with halogen, cyano, nitro, aroyl, aryloxy, aryl, heteroaryl, C1-C6 acyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6. carboalkoxy or amido unsubstituted or substituted with one or two C1-C6 alkyl groups, where RY and RX are independently H, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, aryl or heteroaryl, and(iv)    where * = point of attachment    in which Q1, Q2   are O or S;W   is O, CH2, CHR6, or a bond;R1   is C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, aryl or heteroaryl;R2   is H, C1-C3 alkyl, C2-C5 alkenyl or C2-C5 alkynyl;R3   is H, R1, OR1, OC(O)R1, OC(O)OR1 or OC(O)NR1R6;R4 and R5   are independently H, C1-C6 alkyl, or C2-C6 alkenyl, provided that the sum of carbons for R4 plus R5 is six or less, and further provided that R4 and R5 may be joined into a C3-C6 ring;R6 and R7   are independently H, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C5 alkenyl or C2-C5 alkynyl provided that at least one of R6 and R7 is H;with the proviso that the compound of Formula I is not one of the following:
  2. 6
    A compound of any one of claims 1 to 5 in which Z is O.
  3. 7
    A fungicidal composition comprising the compounds of any one of claims 1 to 6 and a phytologically acceptable carrier.
  4. 9
    A method for the control or prevention of fungal infestation, which method comprises applying to the locus of the fungus or the locus in which the infestation is to be controlled or prevented, a fungicidally effective amount of the compound of any one of claims 1 to 6 or the composition of claims 7 or 8.
  5. 10
    A composition comprising a hydrate, salt or complex of the heterocyclic aromatic amide of any one of claims 1 to 6.
Independent claims5