Patent EA-005216-B1 (EA)
Title: Synergistic insecticidal compositions
Inventor: TREACY MICHAEL FRANK
IPC: A01N43/36
Filed: 2000-03-07
Abstract: 1. A synergistic insecticidal composition comprising a synergistically effective amount of a neuronal sodium channel antagonist and an arylpyrrole insecticide wherein the sodium channel antagonist compound has the structure of formula wherein A is CR4R5 or NR6; W is O or S; X, Y, Z and Z' are each independently H; halogen; OH; CN; optionally NO2; C1-C6alkyl substituted with one or more halogen, C1-C3alkoxy, C1-C3haloalkoxy, or C2-C6alkenyloxy or sulfonyloxy groups; C1-C6 alkoxy optionally substituted with one or more halogen, C1-C3alkoxy or C3-C6cycloalkyl groups; C1-C6alkoxycarbonyl, C3-C6cycloalkylcarbonyloxy, phenyl, optionally substituted with one or more halogen, C1-C4alkyl, or C1-C4alkoxy groups; aminocarbonyloxy optionally substituted with one or more C1-C3alkyl groups; C1-C6alkoxycarbonyloxy; C1-C6alkylsulfonyloxy; C2-C6alkenyl; or NR12R13; m, p and q are each independently an integer of 4, or 5; n is an integer of 0,1 or 2; r is an integer of 1 or 2; t is an integer of 1,2,3 or 4; R, R1, R2, R3, R4 and R5 are each independently H or C1-C4alkyl; R6 is H, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxyalkyl, C1-C6alkoxy, C1-C6alkynyl, C1-C6-C6alkenyl, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylthio, or C1-C6haloalkylthio; R12 and R13 are each independently H or C1-C6alkyl; G is H; C1-C6alkyl optionally substituted with one or more halogen, C1-C4alkoxy, C1-C6haloalkoxy, CN, NO2; S(O)uR17; COR18; CO2R19; phenyl optionally substituted with one or more halogen, CN, C1-C3haloalkyl, or C1-C3haloalkoxy groups; C3-C6cycloalkyl; or phenylthio; Q is phenyl optionally substituted with one or more halogen, CN, SCN, NO2, S(O)uR20, C1-C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxyalkyl, C1-C6alkoxy, C1-C6haloalkoxy or NR21R22 groups; u is an integer of 0,1 or 2; R14, R15, R16, R18, R19, R21 and R22 are each independently H or C1-C6alkyl; R17 and R20 are each independently C1-C6alkyl or C1-C6haloalkyl; R33 is CO2R34; R34 is H, C1-C6alkyl, C1-C6haloalkyl, phenyl or halophenyl; and the dotted line configuration C=N represents a double bond or a single bond; or a stereoisomer thereof and wherein the arylpyrrole insecticide is a compound of formula VI wherein Ar is Hal is Cl or Br; x is an integer of 1,2,3,4,5 or 6; D is H, C1-C6alkyl optionally substituted with one or more halogen, CN, OH, C1-C4alkoxy, C1-C4haloalkoxy, C1-C5alkylthio, C1-C4alkylcarbonyloxy, C1-C4haloalkylthio, C2 C6alkenylcarbonyloxy, phenylcarbonyloxy, halophenylcarbonyloxy, phenoxy, halophenoxy, phenyl, halophenyl or C1-C3alkylphenyl groups; CN, C2-C6alkynyl, C2-C2-C6alkenyl, C2-C6haloalkenyl, C6haloalkynyl, di-(C1-C4alkyl) aminocarbonyl(C1-C4alkyl) aminocarbonyl or C3- C6polymethyleneiminocarbonyl; L is H or halogen; M and M<1> are each independently H, halogen, CN, NO2, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4haloalkylsulfonyl, NR35R36 or when C1-C4alkylcarbonyl, C1-C4haloalkylcarbonyl, M and M<1> are attached to adjacent carbon atoms, they may be taken together with the carbon atoms to which they are attached to form a ring in which MM<1> represents -OCH2O-, -OCF2O- or -CH=CH-CH=CH-; A' is O or S; R30, R31 and R32 are each independently hydrogen, halogen, NO2, CHO or R31 and R32 may be taken together with the carbon atoms to which they are attached to form a ring in which R31 and R32 represent L', L", T and V are each independently H, halogen, CN or NO2 with the proviso that no more than two of L, L", T or V are NO2; and R35 and R36 are each independently H or C1-C4alkyl. 2. The composition according to claim 1 wherein the ratio of the neuronal sodium channel antagonist to the arylpyrrole insecticide is about 1:10 to 1: 50. 3. The composition according to claim 2 wherein said neuronal sodium channel antagonist and said arylpyrrole insecticide are dispersed in an inert solid or liquid diluent. 4. The composition according to claim 1 having a compound of formula I or formula III wherein the dotted line configuration C--N represents a double bond. 5. The composition according to claim 4 wherein W is O; X is trifluoromethoxy and is in the 4-position; Y is trifluoromethyl and is in the 3-position; Z is CN and is in the 4-position; A is CH2; n is 0; m, p and q are each independently 1; R and R1 are each independently H; Z' is Cl; R33 and G are each independently CO2CH3; and Q is p-(trifluoromethoxy)phenyl. 6. The composition according to claim 1 having an arylpyrrole insecticide of formula VI wherein D is H or ethoxymethyl; Ar is phenyl substituted with one or two halogen or halomethyl groups; and x is 1. 7. A method for synergistic insect control which comprises contacting said insect with a synergistically effective amount of a combination of a neuronal sodium channel antagonist and an arylpyrrole insecticide as described in claim 1. 8. The method according to claim 7 wherein the neuronal sodium channel antagonist is present in a ratio to the arylpyrrole insecticide of about 1:10 to 1:50 and having a neuronal sodium channel antagonist compound of formula I or formula III wherein the dotted line configuration C--N represents a double bond and W is O; X is trifluoromethoxy and is in the 4-position; Y is trifluoromethyl and is in the 3-position; Z is CN and is in the 4-position; A is CH2; n is 0; m, p and q are each independently 1; R and R1 are each independently H; Z' is Cl; R33 and G are each independently CO2CH3; and Q is p-(trifluoromethoxy) phenyl. 9. The method according to claim 7 having an arylpyrrole insecticide of formula VI wherein D is H or ethoxymethyl; Ar is phenyl substituted with one or two halogen or halomethyl groups; and x is 1. 10. A method for protecting a plant from infestation and attack by insects which comprises applying to the foliage or stem of said plant a synergistically effective amount of a composition according to claim 1.