TH82155A - Bis derivative (phenyl substituted) -1 - {[4- (saturated heterocyclic - substituted) phenylmethyl] - (4-piperidyl )} Methane with insecticidal activity. - Google Patents

Abstract

DC60 (08/03/49) This is currently found that some derivatives bis (phenyl substituted) -1 - ((4- (heterocyclil at Saturated-displaced) phenylmethyl] (4-piperidil)} new methane has an unexpected insecticide activity. These compounds are represented by formula I; (Chemical formula) I, where R to R15, m, n, s, A, B, D and W are, as defined here, in addition, mixtures contain effective amounts of insecticides of at least one compound. Of Formula I, and as an alternative, the effective quantity of at least one of the second compounds, with at least One of the compatible carriers that exterminate has also been revealed; Simultaneously with the method of Insect control consisting of the application of the mixture to the immediate vicinity of the insect or Was expected to appear It is now found that some derivatives bis (phenyl substituted) -1 - {[4- (heterocyclic at Saturated-displaced) phenylmethyl] (4-piperidil)} new methane has an unexpected insecticide activity. These compounds are represented by formula I; (Chemical formula) I, where R to R15, m, n, s, A, B, D and W are, as defined here, in addition, mixtures contain effective amounts of insecticides of at least one compound. Of Formula I, and as an alternative, the effective quantity of at least one of the second compounds, with at least One of the compatible carriers that exterminate has also been revealed; Simultaneously with the method of Insect control consisting of the application of the mixture to the immediate vicinity of the insect or Was expected to appear

Claims (7)

1. Compounds of formula I: (chemical formula) I where R is chosen from hydrogen, OR16, SR16, halogen, cyano, alkyl, haloalkyl, alkyl silyl, alkoxysilyl, NR16R17, C(=O)R16, NHC(=O)R16, NHC(=O)OR16, NHC(=O)NHR16 and NHC(=S)NHR16; where R16 and R17 are chosen independently of each other from hydrogen, alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, alkyl silyl, alkoxysilyl, aryl, aryl alkyl and heteroaryl; R1 through R10, including, are independently selected from hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, S(O)p-alkyl, S(O)p-haloalkyl, pentahalothio, and nitro; where p is an integer selected from 0, 1, or 2; and R1 and R2, R2 and R3, R6 and R7, and R7 and R8 may concurrently combine with -OC(halogen)2O- to form benzo-fused rings; m is an integer selected from 0 or 1; S is an integer selected from 0 or 1; W is selected from -CR30R31- or OCR30R31-; where R30 and R31 are independently selected from hydrogen or alkyl; R11 through R14, including, are selected independently of each other from hydrogen, halogen, alkyl, haloalkyl, alkoxyalkyl, OR16, S(O)pR16, NR16R17, and aryl; where p, R16, and R17 are as previously described; R15 is selected from hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, OR16, SR16, aryl, arylalkyl, aryloxyalkyl, and heteroaryl; where R16 is as previously described; n is an integer of 0 or 1; And, when n is 0 or 1; A and B are chosen independently of each other from -O(C=O)-, -C(=O)O-, -O(CR18R19)q-, -(CR18R19)qO-, -S(O)p(CR18R19)q-, -(CR18R19)qS(O)p-, -(CR18R19)qNR20- and -NR20(CR18R19)q-, where p is as previously described; and q is an integer chosen from 1 to 7, provided that the sum of q is 8 or less; R18 and R19 were independently selected from hydrogen, alkyl, alkynyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, alkynyloxyalkyl, alryl, alryloxyalkyl, alrylalkoxycarbonyl, aminoalkyl, heterocycloalkyl, and heteroalryl; and R20 was selected from hydrogen, alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, acyl, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alryl, alrylalkyl, xylyl, and phosphoryl. And when n is 1; D is chosen from -O-, -S-, -NR20-, -C=NOR20, -C(halogen)2-, CR21R22-, -C(R21)(OR22)-, -C(OR21)(OR22)-, SiR21R22-, -Si(OR21)(OR22)-, P(=O)rR21, P(=O)r(OR21), BR21, B(OR21), C(=O), C=CR23R24, -CR23=CR24- and (chemical formula); where R20 is as previously described; R21 and R22 are chosen independently, which R21 and R22 are independently selected from hydrogen, alkyl, alkynyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, amino, aryl, and heteroalryl, and where R21 and R22 may simultaneously form a spyro ring; R23 and R24 are independently selected from hydrogen, halogen, alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, alkylsilyl, alkoxysilyl, aryl, aryl alkyl, and heteroalryl; and r is an integer chosen from 0 or 1; Or, when n is 1; A and B are chosen independently of each other from -O-, -S(O)p-, -O(CR18R19)q-, -(CR18R19)qO-, -NR20- and -(CR21R22)t-, where p, q, R18, R19, R20, R21 and R22 are as previously described, and t is an integer chosen from 1, 2, 3 or 4; and; D is the phenylene moity (chemical formula) which, together with A and B, forms a benzo-fused ring, where R25 to R28 are independently selected from hydrogen, halogen, alkyl, haloalkyl, hydroxyalkyl, alkoxy, alkoxyalkoxy, alkylthio, thioalkyl, cyano, alkoxycarbonyl, aryl, aryloxy, heteroaryloxy; or where n is 1; A and B are independently selected from -O-, -S(O)p-, -O(CR18R19))q-, -(CR18 R19)qO-, NR20- and -(CR21R22)t-, where p, q, R18, R19, R20, R21 and R22 are as previously described; and t is an integer chosen from 1, 2, 3 or 4; and, D is the cyclic moitity chosen from; (chemical formula), (chemical formula) (chemical formula) (A), (B) and (C) which, together with A and B, form a fused ring; and salts of these that are agriculturally acceptable; provided that R is OR16 where R16 is hydrogen; m is 0; R11 through R15, in addition to hydrogen; A and B are both -O(CR18R19)q- where R18 and R19 are both hydrogen and q is 1; and n is 0, and i) where R1, R2, R4, R5, R7, R8, R9 and R10 are hydrogen and R3 is trifluoromethoxy, subsequently R6 is in addition to trifluoromethoxy; or ii) when R1, R2, R4, R5, R6, R7, R8, and R9 are hydrogen and R3 is trifluoromethoxy, then R10 is other than trifluoromethoxy; or iii) when R2, R3, R4, R5, R6, R7, R9, and R10 are hydrogen and R8 is trifluoromethoxy, then R1 is other than trifluoromethoxy; or iv) when R1, R2, R3, R4, R6, R7, R9, and R10 are hydrogen and R8 is trifluoromethoxy, then R5 is other than trifluoromethoxy; And provide that when A and B are chosen independently of each other from -C(=O)O-, -(CR18R19)qO- and -(CR18R19)qS(O)p-, then D is not chosen from -O- or -S-. 2. Compounds of claim 1, where R is chosen from hydrogen, fluorine, OR16 and NR16R17, where R16 and R17 are hydrogen; I) R1, R2, R4, R5, R6, R7, R9 and R10 are all hydrogen, and R3 and R8 are all trifluoromethyl or trifluoromethoxy; or ii) R1, R4, R5, R6, R9 and R10 are all hydrogen, and R2, R3, R7 and R8 are chosen independently of each other from fluorine or chlorine, R11 to R14, in addition, are chosen independently of each other from hydrogen, halogen, alkyl and alkoxy; R15 is hydrogen or alkyl; n is 0; A and B are chosen independently of each other from... -O(CR18R19)q-, -S(CR18R19)q-, and -NR20(CR18R19)q-, where p is 0, and q is an integer chosen from 1 to 3. 3. Compounds of claim 2, where R is OR16 and R16 is hydrogen; R1, R2, R4, R5, R6, R7, R9 and R10 are all hydrogen, and R3 and R8 are all trifluoromethyl or trifluoromethoxy; R11 through R13, in addition, are all hydrogen; R14 is hydrogen, halogen or alkyl; q is an integer chosen from 1 to 2; R15 is hydrogen; and R18 and R19 are hydrogen or alkyl. 4. The mixture contains an effective insecticidal quantity of the compound of Claim 1 and at least one agriculturally acceptable coloring or binding agent. 5. The insecticide mixture of claim number 4 also contains one or more second compounds selected from a group of pesticides, plant growth regulators, fertilizers and soil conditioners. 6. The method of insect control consists of applying the effective quantity of the insecticidal mixture of claims under clause 4 to the areas where insects appear or are expected to appear. 7. The method of insect control consists of applying the effective quantity of the insecticidal mixture of claims under clause 5 to areas where insects appear or are expected to appear.