Pesticidal 1-polyarylpyrazoles

Abstract

A compound of formula (I): compositions containing them and methods of use to control pests.

What is claimed is:  
     
       1. A compound of formula (I):                    
       wherein: 
       X is N;  
       Y is C—R 3 ;  
       W is C—R 4 ;  
       R 3  is CN;  
       R 4  is —S(O) n R 8 ;  
       R 5  is —NR 9 R 10 ;  
       R 8  is alkyl, haloalkyl, alkenyl, or alkynyl, or R 8  is a cycloalkyl ring having 3 to 5 carbon atoms;  
       R 9  and R 10 , independently of each other, are H, alkyl, haloalkyl, alkylcarbonyl, haloalkylcarbonyl, R 8 S(O) n , formyl, alkenyl, alkynyl, alkoxycarbonyl, alkylthiocarbonyl, or aroyl, the alkyl portions of R 9  and R 10  being optionally substituted by R 7 ;  
       R 7  is cyano, nitro, alkoxy, haloalkoxy, R 8 S(O) n , —C(O) alkyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, —CO 2 H, halogen, hydroxy, aminosulfonyl, alkylaminosulfonyl or dialkylaminosulfonyl;  
       Z is C—R 16 ;  
       n is zero, one or two;  
       R 12 , R 13 , R 15  and R 16 , independently of one another, are hydrogen, halogen, alkyl, haloalkyl, cyanoalkyl, cyano, nitro, amino, hydrazino, alkoxy, haloalkoxy, alkylsulfenyl, alkylsulfinyl, alkylsulfonyl, haloalkylsulfenyl, haloalkylsulfinyl, haloalkylsulfonyl, formyl, alkylcarbonyl, alkoxycarbonyl;  
       R 22 , R 23 , R 24 , R 25 , and R 26 , independently of one another, are hydrogen, halogen, alkyl, haloalkyl, cyanoalkyl, cyano, nitro, amino, hydrazino, alkoxy, haloalkoxy, haloalkylcarbonyl, formyl, alkylcarbonyl, thioamide, amide, alkoxycarbonyl, SF 5 , or R 8 S(O) n ;  
       or a pesticidally acceptable salt thereof. 
     
     
       2. A compound according to  claim 1 , wherein R 24  is halogen, haloalkyl or haloalkoxy. 
     
     
       3. A compound according to  claim 1 , wherein R 5  is —NH 2 . 
     
     
       4. A compound according to  claim 1 , wherein R 8  is lower alkyl or haloalkyl. 
     
     
       5. A compound according to  claim 1 , having at least one feature selected from the group consisting of: 
       R 8  is methyl, ethyl, —CF 3 , —CFCl 2 , or —CF 2 Cl;  
       R 12  and R 16 , independently of each other, are F, Cl, Br or H;  
       R 13  and R 15  are H;  
       R 24  is —CF 3 , —OCF 3 , —CHF 2 , —S(O) n CF 3 , —CFCl 2 , —CF 2 Cl, —OCF 2 Cl, —OCFCl 2 , Cl, Br or F; and  
       Z is CCl, CF, or CBr.  
     
     
       6. A compound according to  claim 2   claim 5 , wherein R 5  is —NH 2 . 
     
     
       7. A compound according to  claim 1 , wherein: 
       R 12  and R 16 , independently of each other, are Cl or Br;  
       R 13  and R 15  are H;  
       R 24  is —CF 3 , —OCF 3  or Br;  
       R 5  is amino;  
       R 9  and R 10 , independently of each other, are H, alkyl or alkylcarbonyl; and  
       R 8  is methyl, ethyl, CF 3 , CFCl 2  or CF 2 Cl.  
     
     
       8. A compound according to  claim 2   claim 5 , wherein: 
       R 12  and R 16 , independently of each other, are Cl or Br;  
       R 24  is —CF 3 , —OCF 3  or Br;  
       R 5  is amino; and  
       R 9  and R 10 , independently of each other, are H, alkyl or alkylcarbonyl.  
     
     
       9. A compound according to  claim 1 , wherein the S(O) n R 8  substituent of formula (I) is: methylthio, methylsulfinyl, methylsulfonyl, ethylsulfinyl, ethylsulfonyl, ethylthio, cyclopropylsulfinyl, cyclopropylthio, cyclopropylsulfonyl, isopropylsulfinyl, isopropylsulfonyl, isopropylthio, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, dichlorofluoromethylthio, dichlorofluoromethylsulfinyl, dichlorofluoromethylsulfonyl, chlorodifluoromethylthio, chlorodifluoromethylsulfonyl or chlorodifluoromethylsulfinyl. 
     
     
       10. A compound according to  claim 5 , wherein the S(O) n R 8  substituent of formula (I) is: trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, dichlorofluoromethylthio, dichlorofluoromethylsulfinyl, dichlorofluoromethylsulfonyl, chlorodifluoromethylthio, chlorodifluoromethylsulfonyl or chlorodifluoromethylsulfinyl. 
     
     
       11. A compound according to  claim 7 , wherein the S(O) n  R 8  substituent of formula (I) is: trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, dichlorofluoromethylthio, dichlorofluoromethylsulfinyl, dichlorofluoromethylsulfonyl, chlorodifluoromethylthio, chlorodifluoromethylsulfonyl or chlorodifluoromethylsulfinyl. 
     
     
       12. A compound according to  claim 8 , wherein the S(O) n R 8  substituent of formula (I) is: trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, dichlorofluoromethylthio, dichlorofluoromethylsulfinyl, dichlorofluoromethylsulfonyl, chlorodifluoromethylthio, chlorodifluoromethylsulfonyl or chlorodifluoromethylsulfinyl. 
     
     
       13. The compound of formula (I) according to  claim 1 , which is: 
       1-[2,6-dichloro-4-(4-trifluoromethylphenyl)phenyl]-3-cyano-4-trifluoromethylthio-5-aminopyrazole; or  
       1-[2,6-dichloro-4-(4-trifluoromethylphenyl)phenyl]-3-cyano-4-trifluoromethylsulfonyl-5-aminopyrazole.  
     
     
       14. A pesticidal composition comprising: 
       (a) a pesticidally effective amount of a compound of formula (I):                    
       wherein: 
       X is N;  
       Y is C—R 3 ;  
       W is C—R 4 ;  
       R 3  is CN;  
       R 4  is —S(O) n R 8 ;  
       R 5  is —NR 9 R 10 ;  
       R 8  is alkyl, haloalkyl, alkenyl, or alkynyl, or R 8  is a cycloalkyl ring having 3 to 5 carbon atoms;  
       R 9  and R 10 , independently of each other, are H, alkyl, haloalkyl, alkylcarbonyl, haloalkylcarbonyl, R 8 S(O) n , formyl, alkenyl, alkynyl, alkoxycarbonyl, alkylthiocarbonyl, or aroyl, the alkyl portions of R 9  and R 10  being optionally substituted by R 7 ;  
       R 7  is cyano, nitro, alkoxy, haloalkoxy, R 8 S(O) n , —C(O) alkyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, —CO 2 H, halogen, hydroxy, aminosulfonyl, alkylaminosulfonyl or dialkylaminosulfonyl;  
       Z is C—R 16 ;  
       n is zero, one or two;  
       R 12 , R 13 , R 15  and R 16 , independently of one another, are hydrogen, halogen, alkyl, haloalkyl, cyanoalkyl, cyano, nitro, amino, hydrazino, alkoxy, haloalkoxy, alkylsulfenyl, alkylsulfinyl, alkylsulfonyl, haloalkylsulfenyl, haloalkylsulfinyl, haloalkylsulfonyl, formyl, alkylcarbonyl or alkoxycarbonyl;  
       R 22 , R 23 , R 24 , R 25 , and R 26 , independently of one another, are hydrogen, halogen, alkyl, haloalkyl, cyanoalkyl, cyano, nitro, amino, hydrazino, alkoxy, haloalkoxy, haloalkylcarbonyl, formyl, alkylcarbonyl, thioamide, amide, alkoxycarbonyl, SF 5 , or R 8 S(O) n ;  
       or a pesticidally acceptable salt thereof. 
       (b) a pesticidally acceptable carrier therefor.  
     
     
       15. A composition according to  claim 14 , comprising from 0.001 to 95% of compound of formula (I). 
     
     
       16. A method for controlling pests at a locus comprising applying to said locus a pesticidally effective amount of a compound of formula (I):                    
       wherein: 
       X is N;  
       Y is C—R 3 ;  
       W is C—R 4 ;  
       R 3  is H, halogen, hydroxy, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy,  CN;  
       R 4  is —S(O) n R 8 ;  
       R 5  is —NR 9 R 10 ;  
       R 8  is alkyl, haloalkyl, alkenyl, or alkynyl, or R 8  is a cycloalkyl ring having 3 to 5 carbon atoms;  
       R 9  and R 10 , independently of each other, are H, alkyl, haloalkyl, alkylcarbonyl, haloalkylcarbonyl, R 8 S(O) n , formyl, alkenyl, alkynyl, alkoxycarbonyl, alkylthiocarbonyl, or aroyl, the alkyl portions of R 9  and R 10  being optionally substituted by R 7 ;  
       R 7  is cyano, nitro, alkoxy, haloalkoxy, R 8 S(O) n , —C(O) alkyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, —CO 2 H, halogen, hydroxy, aminosulfonyl, alkylaminosulfonyl or dialkylaminosulfonyl;  
       Z is C—R 16 ;  
       n is zero, one or two;  
       R 12 , R 13 , R 15  and R 16 , independently of one another, are hydrogen, halogen, alkyl, haloalkyl, cyanoalkyl, cyano, nitro, amino, hydrazino, alkoxy, haloalkoxy, alkylsulfenyl, alkylsulfinyl, alkylsulfonyl, haloalkylsulfenyl, haloalkylsulfinyl, haloalkylsulfonyl, formyl, alkylcarbonyl or alkoxycarbonyl;  
       R 22 , R 23 , R 24 , R 25 , and R 26 , independently of one another, are hydrogen, halogen, alkyl, haloalkyl, cyanoalkyl, cyano, nitro, amino, hydrazino, alkoxy, haloalkoxy, haloalkylcarbonyl, formyl, alkylcarbonyl, thioamide, amide, alkoxycarbonyl, SF 5 , or R 8 S(O) n ;  
       or a pesticidally acceptable salt thereof. 
     
     
       17. A method according to  claim 16 , wherein said pests are insects and wherein said pesticidally effective amount is an insecticidally effective amount. 
     
     
       18. A method according to  claim 17 , comprising applying to said locus from about 0.01 to about 2 kg/ha of compound of formula (I). 
     
     
       19. A method according to  claim 18 , comprising applying to said locus from about 0.1 to about 1 kg/ha of compound of formula (I). 
     
     
       20. A method for controlling pests at a locus comprising applying to said locus a pesticidally effective amount of a composition as claimed in  claim 14 . 
     
     
       21. A method according to  claim 20 , wherein said pests are insects and wherein said pesticidally effective amount is an insecticidally effective amount.