Nova Patents
IL87222A

Arylpyrroles, methods for thepreparation thereof andinsecticidal, acaricidal andnematicidal compositionscontaining them

Abstract

This record has no abstract on file.

IL87222A, drawing sheet 1
Sheet 1 of 160

Term

No projected expiry on record.

  1. Priority
  2. Filed
  3. Published
  4. Today

12 claims: 4 independent, 8 dependent

  1. 1
    compound having the formula I structure:wherein X is F, Cl, Br, I, or CF^;Y is F, Cl, Br, I, CF^ or CN;W is CN or NO_ and A is H;C.-C. alkyl optionally substituted with from one to three halogen atoms, one hydroxy, one C 1 ־C 4 alkoxy or one C^C* alkylthio, one phenyl optionally substituted with C ]_־ C 3 alkyl or c 1־ c 3 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;c 1־ c 4 carbalkoxymethyl;C 3 ־C 4 alkenyl optionally substituted with from one to three halogen atoms;cyano;C 3 ~C 4 alkynyl optionally substituted with one halogen atom;di-(C 1 ״C 4 alkyl) aminocarbonyl;or c 4“ c 6 cycloalkyl-aminocarbonyl;L is H, F, Cl or Br;and M and R are each independently H, alkyl, C 1 ־C 3 alkoxy, C 1 ־C 3 alkylthio, C 1 ־C 3 alkylsulfinyl, C 1 ־C 3 alkylsulfonyl, cyano, F, Cl, Br, I, nitro, CF 3׳ RjCF.^, R_CO or NR_R., and when M and R are on adjacent 2 3 4 positions and taken with the carbon atoms to which they are attached they may form a ring in which MR represents the structure: -OCHjO-, -OCFpO- Z is S(O)n or 0;R^ is H, F, CHF 2 , CHFC1, or CF 3 ;R 2 is C 1 -C 3 alkyl, Cj-C 3 alkoxy, or NR 3 R 4 ;R 3 is H or C 1 ־C 3 alkyl;R 4 is H, C 1 ־C 3 alkyl, or RgCO;R 5 is H or C 1 ־C 3 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: U π wherein X is F, Cl, Br, I, or CF^;Y is F, Cl, Br, I, CF_ or CN;W is CN or NO- and A is H;C.-C. alkyl optionally substituted with from one to three halogen atoms, one hydroxy, one C 1 ־C 4 alkoxy or one Cj-C 4 alkylthio, one phenyl optionally substituted with c 1 -c 3 alkyl or Cj-Cg 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;c !“ c 4 carbalkoxymethyl;c 3־ c 4 alkenyl optionally substituted with from one to three halogen atoms;cyano;C 3 ־C 4 alkynyl optionally substituted with one halogen atom;di-(C 1 ~C 4 alkyl) aminocarbonyl;or c 4 -c 6 cycloalkyl-aminocarbonyl;L is H, F, Cl or Br;and M and R are each independently H, c ! -c 3 alkyl, C ]_ -C 3 alkoxy, C1־ C 3 alkylthio, <\-0 3 alkylsulfinyl, 0 ! β alkylsulfonyl, cyano, F, Cl, Br, I, nitro, CF_, R.CF.Z, R CO or NR_R., and when M and R are on adjacent A J . positions and taken with the carbon atoms to which they are attached they may form a ring in which MR represents the structure: ־OCHgO־, -OCFgO- Z is S(O)n or 0;R is H, F, CHF , CHFC1, or CF ;R is X M W 4fat C_-C_ alkyl, C.-C_ alkoxy, or NR״R.;R is H or C_-C״ X w X «w w *i Ο X O alkyl;R. is H, C_-C_ alkyl, or R_CO;R_ is H or C_-C_ J 4 1 3 J 5 5 13 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 F, Cl, Br, I, or CF 3 ;Y is F, Cl, Br, f I, CF_ or CN;W is CN or NO״ and A is H;C.-C. alkyl Λ» X *X optionally substituted with from one to three halogen atoms, one hydroxy, one ^ - £4 alkoxy or one alkylthio, one phenyl optionally substituted with alkyl or ^-Cg 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;c ! -c 4 carbalkoxymethyl;C3־C4 alkenyl optionally substituted with from one to three halogen atoms;cyano;Cg -C4 alkynyl optionally substituted with one halogen;di-(C1־C4 alkyl) aminocarbonyl;or c 4“ c 6 cycloalkylaminocarbonyl;L is H, F, Cl or Br;and M and R are each independently H, C1-C 3 alkyl, c 1־ c 3 alkoxy, C.-C, alkylthio, C.-C״ alkylsulfinyl, C-C_ alkylsulXu *1» u XO fonyl, cyano, F, Cl, Br, I, nitro, CFg, R^F^, R 2 CO or NR 3 R 4 , 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: CH 2 0-j -OCF 2 O- or Z is S(O)n or 0;R. is H, F, CHF , CHFC1, X & C.-C, alkyl, C.-C״ alkoxy, or NR,R.;R, Xu Xu u י u alkyl;R 4 is H, ^-Cg alkyl, or RgCO;R 5 alkyl;and n is an integer of 0, 1 or 2. or CF 3 ;R 2 is is H or C 1 ־C 3 is H or C^-Cg
  4. 10
    A method for the preparation of a novel arylpyrrole compound having the structure:wherein X is F, Cl, Br, I, or CF 3 ;Y is F, Cl, Br, I, CF 3 or CN;W is CN or NO_;L is H, F, Cl or Br;and M and z R are each independently H, C^-C^ alkyl, c ^“ c 3 alkoxy, Cj־־C 3 alkylthio, Cj-Cj alkylsulfinyl, C.^.־^ alkylsulfonyl, cyano, F, Cl, Br, I, nitro, CF_, R.CF,Z, R,co or ο x z z NR^R^, 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: ch 2 0- , -ocf 2 o- Z is S(0)n or 0;R. is H, F, CHF,, CHFC1, or CF_;R_ is X Z«3 Z C.-C_ alkyl, C.-C_ alkoxy, or NR_R ;R_ is H or C -C_ J aL W *J *T Wi J alkyl;R. is H, C.-C- alkyl, or R c CO;R_ is H or C.-C, 4 13 5 513 alkyl;and n is an integer of 0, 1 or 2;comprising, reacting a benzoylacetonitrile or a-nitroacetophenone having the structure: // c-ch 2 u wherein L, M, R, and W are as described above with 2,2di(C 1 ~C 4 alkoxy)ethylamine, at an elevated temperature, to yield an a-[2,2-dialkoxy)ethylamino]-^-cyanostyrene or a-[2,2-di(^-^ alkoxy) ethylamino]-0-nitrostyrene having the structure: wherein L, M, R, and W are as described above and treating the thus formed a-[2,2-di(C 1 ־C 4 alkoxy)ethylamino]-β-cyanostyrene or a-[2,2-di(C^־C^ alkoxy)amino]-0-nitrostyrene with a mineral or organic acid to yield the desired arylpyrrole.
Independent claims4