Heterocyclic diamide invertebrate pest control agents

Abstract

This invention provides compounds of Formula (I), N-oxides and suitable salts thereof, wherein A and B are independently O or S; each J is independently a phenyl ring, a naphthyl ring system, a 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system wherein each ring or ring system is optionally substituted with 1 to 4 R 5 ; K is, together with the two contiguous linking carbon atoms, a 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 3 R 4 ; and R 1 , R 2 , R 3 , R 4 , R 5 and n are as defined in the disclosure. Also disclosed are methods for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula (I), an N-oxide thereof or a suitable salt of the compound (e.g., as a composition described herein). This invention also pertains to a composition for controlling an invertebrate pest comprising a biologically effective amount of a compound of Formula (I), an N-oxide thereof or a suitable salt of the compound and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.

What is claimed is:  
     
         1 . A compound of Formula I, an N-oxide thereof or suitable salt thereof  
       
         
           
           
               
               
           
         
       
       wherein 
 A and B are independently O or S;  
 each J is independently a phenyl ring, a naphthyl ring system, a 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system wherein each ring or ring system is optionally substituted with 1 to 4 R 5 ;  
 K is, together with the two contiguous linking carbon atoms, a 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 3 R 4 ;  
 n is 1 to 3;  
 R 1  is H; or C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl or C 3 -C 6  cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO 2 , hydroxy, C 1 -C 4  alkoxy, C 1 -C 4  alkylthio, C 1 -C 4  alkylsulfinyl, C 1 -C 4  alkylsulfonyl, C 2 -C 4  alkoxycarbonyl, C 1 -C 4  alkylamino, C 2 -C 8  dialkylamino and C 3 -C 6  cycloalkylamino; or  
 R 1  is C 2 -C 6  alkylcarbonyl, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  alkylaminocarbonyl, C 3 -C 8  dialkylaminocarbonyl or C(=A)J;  
 R 2  is H, C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 3 -C 6  cycloalkyl, C 1 -C 4  alkoxy, C 1 -C 4  alkylamino, C 2 -C 8  dialkylamino, C 3 -C 6  cycloalkylamino, C 2 -C 6  alkoxycarbonyl or C 2 -C 6  alkylcarbonyl;  
 R 3  is H; G; or C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 3 -C 6  cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of G, halogen, CN, NO 2 , hydroxy, C 1 -C 4  alkoxy, C 1 -C 4  haloalkoxy, C 1 -C 4  alkylthio, C 1 -C 4  alkylsulfinyl, C 1 -C 4  alkylsulfonyl, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  alkylcarbonyl, C 3 -C 6  trialkylsilyl, or a phenyl, phenoxy or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from R 6 ; or  
 R 2  and R 3  can be taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom of nitrogen, sulfur or oxygen, and said ring may be optionally substituted with one to four substituents selected from R 12 ; and  
 G is a 5- or 6-membered nonaromatic carbocyclic or heterocyclic ring, optionally including one or two ring members selected from the group consisting of C(═O), SO or S(O) 2  and optionally substituted with one to four substituents selected from R 12 ;  
 each R 4  is independently H, C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 3 -C 6  cycloalkyl, C 1 -C 6  haloalkyl, C 2 -C 6  haloalkenyl, C 2 -C 6  haloalkynyl, C 3 -C 6  halocycloalkyl, halogen, CN, NO 2 , hydroxy, C 1 -C 4  alkoxy, C 1 -C 4  haloalkoxy, C 1 -C 4  alkylthio, C 1 -C 4  alkylsulfinyl, C 1 -C 4  alkylsulfonyl, C 1 -C 4  haloalkylthio, C 1 -C 4  haloalkylsulfinyl, C 1 -C 4  haloalkylsulfonyl, C 1 -C 4  alkylamino, C 2 -C 8  dialkylamino, C 3 -C 6  cycloalkylamino, C 1 -C 4  alkoxyalkyl, C 1 -C 4  hydroxyalkyl, C(O)R 10 , CO 2 R 10 , C(O)NR 10 R 11 , NR 10 R 11 , N(R 11 )CO 2 R 10 ; or  
 each R 4  is independently a phenyl, benzyl, phenoxy or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from R 6 ;  
 each R 5  is independently H, C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 3 -C 6  cycloalkyl, C 1 -C 6  haloalkyl, C 2 -C 6  haloalkenyl, C 2 -C 6  haloalkynyl, C 3 -C 6  halocycloalkyl, halogen, CN, CO 2 H, CONH 2 , NO 2 , hydroxy, C 1 -C 4  alkoxy, C 1 -C 4  haloalkoxy, C 1 -C 4  alkylthio, C 1 -C 4  alkylsulfinyl, C 1 -C 4  alkylsulfonyl, C 1 -C 4  haloalkylthio, C 1 -C 4  haloalkylsulfinyl, C 1 -C 4  haloalkylsulfonyl, C 1 -C 4  alkylamino, C 2 -C 8  dialkylamino, C 3 -C 6  cycloalkylamino, C 2 -C 6  alkylcarbonyl, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  alkylaminocarbonyl, C 3 -C 8  dialkylaminocarbonyl, C 3 -C 6  trialkylsilyl; or  
 each R 5  is independently a phenyl, benzyl, benzoyl, phenoxy, 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring or ring system optionally substituted with one to three substituents independently selected from R 6 ; or  
 (R 5 ) 2  when attached to adjacent carbon atoms can be taken together as —OCF 2 O—, —CF 2 CF 2 O—, or —OCF 2 CF 2 O—; and  
 each R 6  is independently C 1 -C 4  alkyl, C 2 -C 4  alkenyl, C 2 -C 4  alkynyl, C 3 -C 6  cycloalkyl, C 1 -C 4  haloalkyl, C 2 -C 4  haloalkenyl, C 2 -C 4  haloalkynyl, C 3 -C 6  halocycloalkyl, halogen, CN, NO 2 , C 1 -C 4  alkoxy, C 1 -C 4  haloalkoxy, C 1 -C 4  alkylthio, C 1 -C 4  alkylsulfinyl, C 1 -C 4  alkylsulfonyl, C 1 -C 4  alkylamino, C 2 -C 8  dialkylamino, C 3 -C 6  cycloalkylamino, C 3 -C 6  (alkyl)cycloalkylamino, C 2 -C 4  alkylcarbonyl, C 2 -C 6  alkoxycarbonyl, C 2 -C 6  alkylaminocarbonyl, C 3 -C 8  dialkylaminocarbonyl or C 3 -C 6  trialkylsilyl;  
 each R 10  is independently H, C 1-4  alkyl or C 1 -C 4  haloalkyl;  
 each R 11  is independently H or C 1 -C 4  alkyl; and  
 each R 12  is independently C 1 -C 2  alkyl, halogen, CN, NO 2  or C 1 -C 2  alkoxy.  
 
     
     
         2 . The compound of  claim 1  wherein A and B are both 0 and J is a phenyl ring optionally substituted with 1 to 4 R 5 .  
     
     
         3 . The compound of  claim 2  wherein 
 each R 4  is independently C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, halogen, CN, NO 2  or C 1 -C 4  alkoxy, and one R 4  group is attached to the K ring at the atom adjacent to either the NR 1 C(=A)J moiety or the C(═B)NR 2 R 3  moiety; and  
 each R 5  is independently H, halogen, C 1 -C 4  alkyl, C 1 -C 2  alkoxy, C 1 -C 4  haloalkyl, CN, NO 2 , C 1 -C 4  haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4  alkylsulfinyl, C 1 -C 4  alkylsulfonyl, C 1 -C 4  haloalkylthio, C 1 -C 4  haloalkylsulfinyl, C 1 -C 4  haloalkylsulfonyl or C 2 -C 4  alkoxycarbonyl; or  
 each R 5  is independently a phenyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from R 6 ; or  
 (R 5 ) 2  when attached to adjacent carbon atoms can be taken together as —OCF 2 O—, —CF 2 CF 2 O— or —OCF 2 CF 2 O—.  
 
     
     
         4 . The compound of  claim 3  wherein 
 R 1  is H;  
 R 2  is H or CH 3 ;  
 R 3  is C 1 -C 4  alkyl optionally substituted with one or more substituents independently selected from halogen, CN, OCH 3  or S(O) p CH 3 ;  
 each R 4  is independently CH 3 , CF 3 , CN or halogen, and one R 4  group is attached to the K ring at the atom adjacent to the NR 1 C(=A)J moiety;  
 each R 5  is independently H, halogen, methyl, CF 3 , OCF 3 , OCHF 2 , S(O) p CF 3 , S(O) p CHF 2 , OCH 2 CF 3 , OCF 2 CHF 2 , S(O) p CH 2 CF 3  or S(O) p CF 2 CHF 2 ; or a phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine ring, each ring optionally substituted with one to three substituents independently selected from C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, halogen or CN; and  
 p is 0, 1 or 2.  
 
     
     
         5 . The compound of  claim 4  wherein R 3  is C 1 -C 4  alkyl.  
     
     
         6 . The compound of  claim 1  wherein 
 A and B are both 0;  
 J is a 5- or 6-membered heteroaromatic ring selected from the group consisting of J-1, J-2, J-3, J-4 and J-5, each J optionally substituted with 1 to 3 R 5   
                     
  Q is O, S or NR 5 ; and  
  W, X, Y and Z are independently N or CR 5 , provided that in J-4 and J-5 at least one of W, X, Y or Z is N.  
 
     
     
         7 . The compound of  claim 6  wherein 
 each R 4  is independently C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, halogen, CN, NO 2  or C 1 -C 4  alkoxy, and one R 4  group is attached to the K ring at the atom adjacent to either the NR 1 C(=A)J moiety or the C(═B)NR 2 R 3  moiety; and  
 each R 5  is independently H, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, halogen, CN, NO 2 , C 1 -C 4  haloalkoxy, C 1 -C 4  alkylthio, C 1 -C 4  alkylsulfinyl, C 1 -C 4  alkylsulfonyl, C 1 -C 4  haloalkylthio, C 1 -C 4  haloalkylsulfinyl, C 1 -C 4  haloalkylsulfonyl or C 2 -C 4  alkoxycarbonyl; or a phenyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with R 6 .  
 
     
     
         8 . The compound of  claim 7  wherein 
 J substituted with 1 to 3 R 5  is selected from the group consisting of J-6, J-7, J-8, J-9, J-10, J-11, J-12 and J-13 
                     R 5  is H, C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, or                        V is N, CH, CF, CCl, CBr or CI;    each R 6  and R 7  is independently H, C 1 -C 6  alkyl, C 3 -C 6  cycloalkyl, C 1 -C 6  haloalkyl, halogen, CN, C 1 -C 4  alkoxy, C 1 -C 4  haloalkoxy or C 1 -C 4  haloalkylthio; and      R 9  is H, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 3 -C 6  alkenyl, C 3 -C 6  haloalkenyl, C 3 -C 6  alkynyl or C 3 -C 6  haloalkynyl; provided R 7  and R 9  are not both H.    
 
     
     
         9 . The compound of  claim 8  wherein V is N.  
     
     
         10 . The compound of  claim 8  wherein V is CH, CF, CCl or CBr.  
     
     
         11 . The compound of  claim 9  or  claim 10  wherein 
 R 1  is H;  
 R 2  is H or CH 3 ;  
 R 3  is C 1 -C 4  alkyl optionally substituted with one or more substituents independently selected from halogen, CN, OCH 3  or S(O) p CH 3 ;  
 each R 4  is independently CH 3 , CF 3 , CN or halogen, and one R 4  group is attached to the K ring at the atom adjacent to the NR 1 C(=A)J moiety;  
 R 6  is C 1 -C 4  alkyl, C 1 -C 4  haloalkyl, halogen or CN;  
 R 7  is H, CH 3 , CF 3 , OCH 2 CF 3 , OCHF 2  or halogen; and  
 p is 0, 1 or 2.  
 
     
     
         12 . The compound of  claim 11  wherein R 3  is C 1 -C 4  alkyl; one R 4  group is independently CH 3 , Cl, Br or I and is attached to the K ring at the atom adjacent to the NR 1 C(=A)J moiety; and a second optional R 4  is H, F, Cl, Br, I or CF 3 .  
     
     
         13 . The compound of  claim 12  wherein J substituted with 1 to 3 R 5  is J-6; R 6  is Cl or Br; and R 7  is halogen, OCH 2 CF 3  or CF 3 .  
     
     
         14 . The compound of  claim 13  wherein V is N; R 3  is methyl, ethyl, isopropyl, tertiary butyl or N(CH 3 ) 2 ; and R 7  is Br, Cl, OCH 2 CF 3 , or CF 3 .  
     
     
         15 . The compound of  claim 12  wherein J substituted with 1 to 3 R 5  is J-7; R 6  is Cl or Br; and R 9  is CF 3 , CHF 2 , CH 2 CF 3  or CF 2 CHF 2 .  
     
     
         16 . The compound of  claim 12  wherein J substituted with 1 to 3 R 5  is J-8; R 6  is Cl or Br; and R 7  is halogen, OCH 2 CF 3  or CF 3 .  
     
     
         17 . The compound of  claim 12  wherein J substituted with 1 to 3 R 5  is J-9; R 6  is Cl or Br; and R 7  is OCH 2 CF 3  or CF 3 .  
     
     
         18 . The compound of  claim 12  wherein J substituted with 1 to 3 R 5  is J-10; R 6  is Cl or Br; and R 9  is CF 3 , CHF 2 , CH 2 CF 3  or CF 2 CHF 2 .  
     
     
         19 . The compound of  claim 12  wherein J substituted with 1 to 3 R 5  is J-11; R 6  is Cl or Br; and R 7  is halogen, OCH 2 CF 3  or CF 3 .  
     
     
         20 . The compound of  claim 12  wherein J substituted with 1 to 3 R 5  is J-12; R 6  is Cl or Br; R 7  is H, halogen or CF 3 , and R 9  is H, CF 3 , CHF 2 , CH 2 CF 3 , or CF 2 CHF 2 .  
     
     
         21 . The compound of  claim 12  wherein J substituted with 1 to 3 R 5  is J-13; R 6  is Cl or Br; R 7  is H, halogen or CF 3 , and R 9  is H, CF 3 , CHF 2 , CH 2 CF 3  or CF 2 CHF 2 .  
     
     
         22 . The compound of  claim 1  selected from the group consisting of: 
 4-[[[1-(2-Chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl]amino]-5-methyl-N-1-methylethyl)-3-pyridincarboxamide,  
 4-Methyl-N-(1-methylethyl)-3-[[2-methyl-4-(trifluoromethyl)benzoyl]amino]-2-thiophencarboxamide,  
 1-Methyl-N-(1-methylethyl)-5-[[4-(trifluoromethyl)benzoyl]amino]-1H-pyrazole-4-carboxamide;  
 4-[[[3-Bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]carbonyl]amino]-5-chloro-N-methyl-3-pyridinecarboxamide;  
 3-[[[3-Bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]carbonyl]amino]-2,6-dichloro-N-methyl-4-pyridinecarboxamide;  
 2,6-dichloro-3-[[[1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl]amino]-N-(1-methylethyl)-4-pyridinecarboxamide;  
 3-[[[3-Bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]carbonyl]amino]-6-chloro-N,4-dimethyl-2-pyridinecarboxamide;  
 3-[[[3-Bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]carbonyl]amino]-4,6-dichloro-N-methyl-2-pyridinecarboxamide;  
 5-[[[3-Chloro-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]carbonyl]amino]-N,625 dimethyl-4-pyrimidinecarboxamide; and  
 5-[[[3-Bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]carbonyl]amino]-N,N,2,6-tetramethyl-4-pyridinecarboxamide.  
 
     
     
         23 . A method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of  claim 1 .  
     
     
         24 . The method of  claim 23  further comprising a biologically effective amount of at least one additional compound or agent for controlling invertebrate pests.  
     
     
         25 . A composition for controlling an invertebrate pest comprising a biologically effective amount of a compound of  claim 1  and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.  
     
     
         26 . The composition of  claim 25  further comprising a biologically effective amount of at least one additional compound or agent for controlling invertebrate pests.