Nova Patents
EP0347488A1

Arylpyrrole insecticidal acaricidal and nematicidal agents and method for the preparation thereof.

Abstract

wherein X is F, Cl, Br, I, or CF₃; Y is F, Cl, Br, I, CF₃ or CN; W is CN or NO₂ and A is H; C₁-C₄ alkyl optionally substituted with from one to three halogen atoms, one hydroxy, one C₁-C₄ alkoxy or one C₁-C₄ alkylthio, one phenyl optionally substituted with C₁-C₃ alkyl or C₁-C₃ alkoxy or with one to three halogen atoms, one phenoxy optionally substituted with one to three halogen atoms or one benzyloxy optionally substituted with one halogen substituent; C₁-C₄ carbalkoxymethyl; C₃-C₄ alkenyl optionally substituted with from one to three halogen atoms; cyano; C₃-C₄ alkynyl optionally substituted with one halogen atom; di-(C₁-C₄ alkyl) aminocarbonyl; or C₄-C₆ cycloalkyl-aminocarbonyl; L is H, F, Cl or Br; and M and R are each independently H, C₁-C₃ alkyl, C₁-C₃ alkoxy, C₁-C₃ alkylthio, C₁-C₃ alkylsulfinyl, C₁-C₃ alkylsulfonyl, cyano, F, Cl, Br, I, nitro, CF₃, R₁CF₂Z, R₂CO or NR₃R₄, and when M and R are on adjacent positions and taken with the carbon atoms to which they are attached they may form a ring in which MR represents the structure: Z is S(O)n or O; R₁ is H, F, CHF₂, CHFCl, or CF₃; R₂ is C₁-C₃ alkyl, C₁-C₃ alkoxy, or NR₃R₄; R₃ is H or C₁-C₃ alkyl; R₄ is H, C₁-C₃ alkyl, or R₅CO; R₅ is H or C₁-C₃ alkyl; and n is an integer of 0, 1 or 2 have insecticidal, acaricidal or nematicidal activity.

EP0347488A1, drawing sheet 1
Sheet 1 of 125

Term

Term ended

Projected expiry passed 5 August 2008, 18.1 years ago.

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16 claims: 7 independent, 9 dependent

  1. 1
    A compound having the formula I structure:wherein X is F, Cl, Br, I, or CF₃;Y is F, Cl, Br, I, CF₃ or CN;W is CN or NO₂ and A is H;C₁-C₄ alkyl optionally substituted with from one to three halogen atoms, one hydroxy, one C₁-C₄ alkoxy or one C₁-C₄ alkylthio, one phenyl optionally substituted with C₁-C₃ alkyl or C₁-C₃ alkoxy or with one to three halogen atoms, one phenoxy optionally substituted with one to three halogen atoms or one benzyloxy optionally substituted with one halogen substituent;C₁-C₄ carbalkoxymethyl;C₃-C₄ alkenyl optionally substituted with from one to three halogen atoms;cyano;C₃-C₄ alkynyl optionally substituted with one halogen atom;di-(C₁-C₄ alkyl) aminocarbonyl;or C₄-C₆ cycloalkyl-aminocarbonyl;L is H, F, Cl or Br;and M and R are each independently H, C₁-C₃ alkyl, C₁-C₃ alkoxy, C₁-C₃ alkylthio, C-C₃ alkylsulfinyl, C₁-C₃ alkylsulfonyl, cyano, F, Cl, Br, I, nitro, CF₃, R₁CF₂Z, R₂CO or NR₃R₄, and when M and R are on adjacent positions and taken with the carbon atoms to which they are attached they may form a ring in which MR represents the structure: Z is S(O)n or O;R₁ is H, F, CHF₂, CHFCl, or CF₃;R₂ is C₁-C₃ alkyl, C₁-C₃ alkoxy, or NR₃R₄;R₃ is H or C₁-C₃ alkyl;R₄ is H, C₁-C₃ alkyl, or R₅CO;R₅ is H or C₁-C₃ alkyl;and n is an integer of 0, 1 or 2.
  2. 4
    A method for controlling insects, nematodes and acarina comprising:contacting said insects, nematodes and acarina, their breeding grounds, food supply or habitat with an insecticidally, nematicidally and acaricidally effective amount of a compound having the structure: wherein X is H, F, Cl, Br, I, or CF₃;Y is F, Cl, Br, I, CF₃ or CN;W is CN or NO₂ and A is H;C₁-C₄ alkyl optionally substituted with from one to three halogen atoms, one hydroxy, one C₁-C₄ alkoxy or one C₁-C₄ alkylthio, one phenyl optionally substituted with C₁-C₃ alkyl or C₁-C₃ alkoxy or with one to three halogen atoms, one phenoxy optionally substituted with one to three halogen atoms or one benzyloxy optionally substituted with one halogen substituent;C₁-C₂ carbalkoxymethyl;C₃-C₄ alkenyl optionally substituted with from one to three halogen atoms;cyano;C₃-C₄ alkynyl optionally substituted with one halogen atom;di-(C₁-C₄ alkyl) aminocarbonyl;or C₄-C₆ cycloalkyl-aminocarbonyl;L is H, F, Cl or Br;and M and R are each independently H, C₁-C₃ alkyl, C₁-C₃ alkoxy, C₁-C₃ alkylthio, C₁-C₃ alkylsulfinyl, C₁-C₃ alkylsulfonyl, cyano, F, Cl, Br, I, nitro, CF₃, R₁CF₂Z, R₂CO or NR₃R₄, and when M and R are on adjacent positions and taken with the carbon atoms to which they are attached they may form a ring in which MR represents the structure: Z is S(O)n or O;R is H, F, CHF₂, CHFCl, or CF₃;R₂ is C₁-C₃ alkyl, C₁-C₃ alkoxy, or NR₃R₄;R₃ is H or C₁-C₃ alkyl;R₄ is H, C₁-C₃ alkyl, or R₅CO;R₅ is H or C₁-C₃ alkyl;and n is an integer of 0, 1 or 2.
  3. 6
    A method for protecting growing plants from attack by insects, nematodes and acarina, comprising applying to the foliage of said plants or to the soil or water in which they are growing, an insecticidally, nematicidally or acaricidally, effective amount of a formula I compound having the structure:wherein X is H, F, Cl, Br, I, or CF₃;Y is F, Cl, Br, I, CF₃ or CN;W is CN or NO₂ and A is H;C₁-C₄ alkyl optionally substituted with from one to three halogen atoms, one hydroxy, one C₁-C₄ alkoxy or one C₁-C₄ alkylthio, one phenyl optionally substituted with C₁-C₃ alkyl or C₁-C₃ alkoxy or with one to three halogen atoms, one phenoxy optionally substituted with one to three halogen atoms or one benzyloxy optionally substituted with one halogen substituent;C₁-C₄ carbalkoxymethyl;C₃-C₄ alkenyl optionally substituted with from one to three halogen atoms;cyano;C₃-C₄ alkynyl optionally substituted with one halogen;di-(C₁-C₄ alkyl) aminocarbonyl;or C₄-C₆ cycloalkylaminocarbonyl;L is H, F, Cl or Br;and M and R are each independently H, C₁-C₃ alkyl, C₁-C₃ alkoxy, C₁-C₃ alkylthio, C₁-C₃ alkylsulfinyl, C₁-C₃ alkylsul­fonyl, cyano, F, Cl, Br, I, nitro, CF₃, R₁CF₂Z, R₂CO or NR₃R₄, and when M and R are on adjacent positions and taken with the carbon atoms to which they are attached they may form a ring in which MR represents the structure: Z is S(O)n or O;R is H, F, CHF₂, CHFCl, or CF₃;R₂ is C₁-C₃ alkyl, C₁-C₃ alkoxy, or NR₃R₄;R₃ is H or C₁-C₃ alkyl;R₄ is H, C₁-C₃ alkyl, or R₅CO;R₅ is H or C₁-C₃ alkyl;and n is an integer of 0, 1 or 2.
  4. 10
    A method for the preparation of a novel arylpyrrole compound having the structure:wherein W is CN or NO₂;L is H, F, Cl or Br;and M and R are each independently H, C₁-C₃ alkyl, C₁-C₃ alkoxy, C₁-C₃ alkylthio, C₁-C₃ alkylsulfinyl, C₁-C₃ alkylsul­fonyl, cyano, F, Cl, Br, I, nitro, CF₃, R₁CF₂Z, R₂CO or NR₃R₄, and when M and R are on adjacent positions and taken with the carbon atoms to which they are attached they may form a ring in which MR represents the structure: Z is S(O)n or O;R₁ is H, F, CHF₂, CHFCl, or CF₃;R₂ is C₁-C₃ alkyl, C₁-C₃ alkoxy, or NR₃R₄;R₃ is H or C₁-C₃ alkyl;R₄ is H, C₁-C₃ alkyl, or R₅CO;R₅ is H or C₁-C₃ alkyl;and n is an integer of 0, 1 or 2;comprising, reacting a benzoylacetonitrile or α-nitroacetophenone having the structure: wherein L, M, R, and W are as described above with 2,2-­di(C₁-C₄ alkoxy)ethylamine, at an elevated temperature, to yield an α-[2,2-di(C₁-C₄ alkoxy)ethylamino]-β-cyano­styrene or α-[2,2-di(C₁-C₄ alkoxy)ethylamino]-β-nitro­styrene having the structure: wherein L, M, R, and W are as described above and treating the thus formed α-[2,2-di(C₁-C₄ alkoxy)ethyl­amino]-β-cyanostyrene or α-[2,2-di(C₁-C₄ alkoxy)amino]-β-nitrostyrene with a mineral or organic acid to yield the desired arylpyrrole.
  5. 13
    A process for the preparation of an α-­[2,2-di(C₁-C₄ alkoxy)ethylamino]-β-cyanostyrene or α-­[2,2-di(C₁-C₄ alkoxy)ethylamino]-β-nitrostyrene repre­sented by the structure:wherein W is CN or NO₂;L is H, F, Cl, or Br;M and R are each independently H, C₁-C₃ alkyl, C₁-C₃ alkoxy, C₁-C₃ alkylthio, C₁-C₃ alkylsulfinyl, C₁-C₃ alkylsul­fonyl, cyano, F, Cl, Br, I, nitro, CF₃, R₁CF₂Z, R₂CO, or NR₃R₄ and when on adjacent positions and taken together with the carbon atoms to which they are attached M and R may form a ring in which MR represent the structure: Z is S(O)n or O;R is H, F, CHF₂, CHFCl, or CF₃;R₂ is C₁-C₃ alkyl, C₁-C₃ alkoxy, or NR₃R₄;R₃ is H or C₁-C₃ alkyl;R₄ is H, C₁-C₃ alkyl, or R₅CO;R₅ is H or C₁-C₃ alkyl;and n is an integer of 0, 1 or 2;comprising, reacting a benzoylacetonitrile or α-nitroacetophenone having the structure: wherein L, M, R, and W are as described above with 2,2-­diethoxyethylamine, at an elevated temperature, to yield an α-(2,2-di(C₁-C₄ alkoxy)ethylamino)-β-cyanostyrene or α-(2,2-di(C₁-C₄ alkoxy)ethylamino)-β-nitrostyrene the structure: wherein L, M, R, and W are as described above.
  6. 14
    A compound having the structural formula:wherein W is CN or NO₂;L is H, F, Cl, or Br;M and R are each independently H, C₁-C₃ alkyl, C₁-C₃ alkoxy, C₁-C₃ alkylthio, C₁-C₃ alkylsulfinyl, C₁-C₃ alkylsul­fonyl, cyano, F, Cl, Br, I, nitro, CF₃, R₁CF₂Z, R₂CO, or NR₃R₄ and when on adjacent positions and taken together with the carbon atoms to which they are attached M and R may form a ring in which MR represent the structure: Z is S(O)n or O;R₁ is H, F, CHF₂, CHFCl, or CF₃;R₂ is C₁-C₃ alkyl, C₁-C₃ alkoxy, or NR₃R₄;R₃ is H or C₁-C₃ alkyl;R₄ is H, C₁-C₃ alkyl, or R₅CO;R₅ is H or C₁-C₃ alkyl;and n is an integer of 0, 1 or 2.
  7. 16
    A process for the preparation of a compound represented by the structure:wherein W is CN or NO₂;L is H, F, Cl, or Br;M and R are each independently H, C₁-C₃ alkyl, C₁-C₃ alkoxy, C₁-C₃ alkylthio, C₁-C₃ alkylsulfinyl, C₁-C₃ alkylsul­fonyl, cyano, F, Cl, Br, I, nitro, CF₃, R₁CF₂Z, R₂CO, or NR₃R₄ and when on adjacent positions and taken together with the carbon atoms to which they are attached M and R may form a ring in which MR represent the structure: Z is S(O)n or O;R is H, f, CHF₂, CHFCl, or CF₃;R₂ is C₁-C₃ alkyl, C₁-C₃ alkoxy, or NR₃R₄;R₃ is H or C₁-C₃ alkyl;R₄ is H, C₁-C₃ alkyl, or R₅CO;R₅ is H or C₁-C₃ alkyl;and n is an integer of 0, 1 or 2;comprising, reacting a benzoylacetonitrile or α-nitroacetophenone having the structure: wherein L, M, R, and W are as described above with 2,2-­di(C₁-C₄ alkoxy)ethylamine, at an elevated temperature, to give a compound having the structure: wherein L, M, R, and W are as described above.
Independent claims7