Chemical compounds

Abstract

A compound of formula I wherein Y is a single bond, C═O, C═S or S(O) m where m is 0, 1 or 2; the ring is a 6-membered aromatic or is a 5 or 6 membered heteroaromatic ring; Z and Z′ are joined by a single or a double bond and are ═C— or —N— provided that both are not N; Ra, R 1 , R 2 , R 3 , R 3a , R 4 and R 8 are specified organic groups; n is 2, 3 or 4 and p is 0-4; or salts or N-oxides thereof.

1 . A compound of formula (I): 
       
         
           
           
               
               
           
         
       
       Y is a single bond, C═O, C═S or S(O) m  where m is 0, 1 or 2; 
       the ring 
       
         
           
           
               
               
           
         
       
       is a 6 membered aromatic ring or is a 5 or 6 membered heteroaromatic ring;
 Z and Z′ are joined by a single or a double bond and are each independently ═C— or —N— provided that both are not N; 
 R 1  is hydrogen, optionally substituted alkyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, aminocarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted heterocyclyloxy, cyano, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, formyl, optionally substituted heterocyclyl, optionally substituted alkylthio, NO or NR 13 R 14 ; 
 R 13  and R 14  are each independently hydrogen, COR 15 , optionally substituted alkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl or R 13  and R 14  together with the N atom to which they are attached form a group —N═C(R 16 )—NR 17 R 18  or R 13  and R 14  together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further heteroatoms selected from O, N or S and which may be optionally substituted by one or two C 1-6  alkyl groups; 
 R 15  is H, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted aryloxy optionally substituted heteroaryl, optionally substituted heteroaryloxy or NR 19 R 20 ; 
 R 16 , R 17  and R 18  are each independently H or lower alkyl; 
 R 19  and R 20  are independently optionally substituted alkyl, optionally substituted aryl or optionally substituted heteroaryl; 
 R 2  is H, hydroxy, optionally substituted alkoxy or optionally substituted alkyl; or R 1  and R 2  together with the groups Y and N form a 5- or 6-membered heterocyclic ring which may optionally contain one further heteroatom selected from O, N or S and which may be optionally substituted by C 1-4  alkyl, C 1-4  haloalkyl or halogen; 
 R 3  is H, OH, halogen or optionally substituted alkyl; 
 R 3a  is H or R 3  and R 3a  together form a bond; 
 two adjacent groups R 4  together with the atoms to which they are attached form a 4, 5, 6, or 7 membered carbocyclic, heteroaromatic, or heterocyclic ring optionally carrying one, two or three R 5  groups; provided that when the two adjacent R 4  groups are both attached to carbon atoms to form a carbocyclic or heterocyclic ring then the resulting carbocyclic or heterocyclic ring is substituted with a substituent other than halogen, C 1-8  alkoxy, C 1-6  haloalkoxy, phenoxy (optionally substituted by halo, nitro, cyano, C 1-6  alkyl, C 1-6  haloalkyl, C 1-6  alkoxy or C 1-6  haloalkoxy), heteroaryloxy (optionally substituted by halo, nitro, cyano, C 1-6  alkyl, C 1-6  haloalkyl, C 1-6  alkoxy or C 1-6  haloalkoxy), C 1-8  alkylthio or R 19 R 20 N; 
 R 19  and R 20  are each independently hydrogen, C 1-8  alkyl, C 3-7  cycloalkyl, C 3-6  alkenyl, C 3-6  alkynyl, C 2-6  haloalkyl, or C 1-6  alkoxycarbonyl or R 19  and R 20  together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further heteroatoms selected from O, N or S and which may be optionally substituted by one or two C 1-6  alkyl groups; 
 optionally any further R 4  groups are each independently halogen, nitro, cyano, thiocyanato, optionally substituted C 1-8  alkyl, optionally substituted C 2-6  alkenyl, optionally substituted C 2-6  alkynyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, optionally substituted C 3-7  cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted alkylthio, arylthio, heteroarylthio, alkylsulfoxyl, arylsulfoxyl, heteroarylsulfoxyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl or R 23 R 24 N; 
 R 23  and R 24  are each independently hydrogen, C 1-8  alkyl, C 3-7  cycloalkyl, C 3-6  alkenyl, C 3-6  alkynyl, C 3-7  cycloalkyl(C 1-4 )alkyl, C 2-6  haloalkyl, C 1-6  alkoxy(C 1-6 )alkyl, C 1-6  alkoxycarbonyl or R 23  and R 24  together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further heteroatoms selected from O, N or S and which may be optionally substituted by one or two C 1-6  alkyl groups; 
 n is 2, 3 or 4; 
 each R 5  is independently halogen, nitro, cyano, thiocyanato, optionally substituted C 1-8  alkyl, optionally substituted C 2-6  alkenyl, optionally substituted C 2-6  alkynyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, optionally substituted C 3-7  cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted alkylthio, arylthio, heteroarylthio, alkylsulfoxyl, arylsulfoxyl, heteroarylsulfoxyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl or R 25 R 26 N; 
 R 25  and R 26  are each independently hydrogen, C 1-8  alkyl, C 3-7  cycloalkyl, C 3-6  alkenyl, C 3-6  alkynyl, C 3-7  cycloalkyl(C 1-4 )alkyl, C 2-6  haloalkyl, C 1-6  alkoxy(C 1-6 )alkyl, C 1-6  alkoxycarbonyl or R 25  and R 26  together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further heteroatoms selected from O, N or S and which may be optionally substituted by one or two C 1-6  alkyl groups; 
 R 8  is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl or optionally substituted alkenylcarbonyl; 
 each Ra is independently halogen, hydroxy, cyano, optionally substituted C 1-8  alkyl, optionally substituted C 2-6  alkenyl, optionally substituted C 2-6  alkynyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, optionally substituted C 3-7  cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted alkylthio, optionally substituted arylthio or R 29 R 30 N; 
 R 29  and R 30  are each independently hydrogen, C 1-8  alkyl, C 3-7  cycloalkyl, C 3-6  alkenyl, C 3-6  alkenyl, C 3-7  cycloalkyl(C 1-4 alkyl, C 2-6  haloalkyl, C 1-6  alkoxy(C 1-6 )alkyl, or C 1-6  alkoxycarbonyl; 
 or R 29  and R 30  together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further heteroatoms selected from O, N or S and which may be optionally substituted by one or two C 1-6  alkyl groups; 
 or two Ra groups attached to the same carbon atom are ═O, ═S, ═NRb, ═CRcRd; 
 Rb, Rc and Rd are each independently H or optionally substituted alkyl; and 
 p is 0, 1, 2, 3 or 4; 
 
       or salts or N-oxides thereof. 
     
     
         2 . The compound according to  claim 1  wherein two adjacent groups R 4  together with the atoms to which they are attached in ring 
       
         
           
           
               
               
           
         
       
       form a 5, 6 or 6,6 fused ring wherein the ring members are each independently CH, S, N, NR 5 , O, or CR 5  where each R 5  is independently as defined in  claim 1  provided that there are no more than one O or S atoms present in the ring. 
     
     
         3 . The compound according to  claim 1  wherein:
 R 8  is C 1-10  alkyl, C 1-10  haloalkyl, aryl(C 1-6 )alkyl (wherein the aryl group is optionally substituted by halogen, C 1-4  alkyl, C 1-4  alkoxy, C 1-4  haloalkyl, C 1-4  haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino), heteroaryl(C 1-6 )alkyl (wherein the heteroaryl group is optionally substituted by halogen, C 1-4  alkyl, C 1-4  alkoxy, C 1-4  haloalkyl, C 1-4  haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino), arylcarbonyl-(C 1-6 )alkyl (wherein the aryl group may be optionally substituted by halogen, C 1-4  alkyl, C 1-4  alkoxy, C 1-4  haloalkyl, C 1-4  haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino and the alkyl group may be optionally substituted by aryl), C 2-8  alkenyl, C 2-8  haloalkenyl, aryl(C 2-6 )-alkenyl (wherein the aryl group is optionally substituted halogen, C 1-4  alkyl, C 1-4  alkoxy, C 1-4  haloalkyl, C 1-4  haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino, C 1-6  alkoxycarbonyl, or two adjacent substituents can cyclise to form a 5, 6 or 7 membered carbocyclic or heterocyclic ring), heteroaryl(C 2-6 )-alkenyl (wherein the heteroaryl group is optionally substituted halogen, C 1-4  alkyl, C 1-4  alkoxy, C 1-4  haloalkyl, C 1-4  haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino, C 1-6  alkoxycarbonyl, or two adjacent substituents can cyclise to form a 5, 6 or 7 membered carbocyclic or heterocyclic ring), C 2-6  alkynyl, 
 
       phenyl(C 2-6 )alkynyl (wherein the phenyl group is optionally substituted by halogen, C 1-4  alkyl, C 1-4  alkoxy, C 1-4  haloalkyl, C 1-4  haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino), C 3-7  cycloalkyl, C 1-6  alkoxycarbonyl, C 1-6  alkylcarbonyl, C 1-6  haloalkylcarbonyl or aryl(C 2-6 )alkenylcarbonyl (wherein the aryl group may be optionally substituted halogen, C 1-4  alkyl, C 1-4  alkoxy, C 1-4  haloalkyl, C 1-4  haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino), or 
       —C(R 51 )(R 52 )—[CR 53 ═CR 54 ]z-R 55  where z is 1 or 2, R 51  and R 52  are each independently H, halo or C 1-2  alkyl, R 53  and R 54  are each independently H, halogen, C 1-4  alkyl or C 1-4  haloalkyl and R 55  is optionally substituted aryl or optionally substituted heteroaryl. 
     
     
         4 . The compound according to  claim 1  wherein Y is a single bond, C═O or C═S. 
     
     
         5 . The compound according to  claim 1 :
 wherein R 1  is hydrogen, C 1-6  alkyl, C 1-6  cyanoalkyl, C 1-6  haloalkyl, C 3-7  cycloalkyl(C 1-4 )alkyl, C 1-6  alkoxy(C 1-6 )alkyl, heteroaryl(C 1-6 )alkyl (wherein the heteroaryl group may be optionally substituted by halo, nitro, cyano, C 1-6  alkyl, C 1-6  haloalkyl, C 1-6  alkoxy, C 1-6  haloalkoxy, C 1-6  alkylsulfonyl, C 1-6  alkylsulfinyl, C 1-6  alkylthio, C 1-6  alkoxycarbonyl, C 1-6  alkylcarbonylamino, arylcarbonyl, or two adjacent positions on the heteroaryl system may be cyclised to form a 5, 6 or 7 membered carbocyclic or heterocyclic ring, itself optionally substituted with halogen), aryl(C 1-6 )alkyl (wherein the aryl group may be optionally substituted by halo, nitro, cyano, C 1-6  alkyl, C 1-6  haloalkyl, C 1-6  alkoxy, C 1-6  haloalkoxy, C 1-6  alkylsulfonyl, C 1-6  alkylsulfinyl, C 1-6  alkylthio, C 1-6  alkoxycarbonyl, C 1-6  alkylcarbonylamino, arylcarbonyl, or two adjacent positions on the aryl system may be cyclised to form a 5, 6 or 7 membered carbocyclic or heterocyclic ring, itself optionally substituted with halogen), C 1-6  alkylcarbonylamino(C 1-6 )alkyl, aryl (which may be optionally substituted by halo, nitro, cyano, C 1-6  alkyl, C 1-6  haloalkyl, C 1-6  alkoxy, C 1-6  haloalkoxy, C 1-6  alkylsulfonyl, C 1-6  alkylsulfinyl, C 1-6  alkylthio, C 1-6  alkoxycarbonyl, C 1-6  alkylcarbonylamino, arylcarbonyl, or two adjacent positions on the aryl system may be cyclised to form a 5, 6 or 7 membered carbocyclic or heterocyclic ring, itself optionally substituted with halogen), heteroaryl (which may be optionally substituted by halo, nitro, cyano, C 1-6  alkyl, C 1-6  haloalkyl, C 1-6  alkoxy, C 1-6  haloalkoxy, C 1-6  alkylsulfonyl, C 1-6  alkylsulfinyl, C 1-6  alkylthio, C 1-6  alkoxycarbonyl, C 1-6  alkylcarbonylamino, arylcarbonyl, or two adjacent positions on the heteroaryl system may be cyclised to form a 5, 6 or 7 membered carbocyclic or heterocyclic ring, itself optionally substituted with halogen), C 1-6  alkoxy, C 1-6  haloalkoxy, phenoxy (wherein the phenyl group is optionally substituted by halogen, C 1-4  alkyl, C 1-4  alkoxy, C 1-4  haloalkyl, C 1-4  haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino), heteroaryloxy (optionally substituted by halo, nitro, cyano, C 1-6  alkyl, C 1-6  haloalkyl, C 1-6  alkoxy or C 1-6  haloalkoxy), heterocyclyloxy (optionally substituted by halo, C 1-6  alkyl, C 1-6  haloalkyl, C 1-6  alkoxy or C 1-6  haloalkoxy), cyano, C 2-6  alkenyl, C 2-6  alkynyl, C 3-6  cycloalkyl, C 5-7  cycloalkenyl, heterocyclyl (optionally substituted by halo, nitro, cyano, C 1-6  alkyl, C 1-6  haloalkyl, C 1-6  alkoxy or C 1-6  haloalkoxy), C 1-6  alkylthio, C 1-6  haloalkylthio or NR 13 R 14 ;   R 13  and R 14  are each independently hydrogen, C 1-6  alkyl, C 1-6  haloalkyl, C 1-6  alkoxy(C 1-6 )alkyl, phenyl (which may be optionally substituted by halogen, C 1-4  alkyl, C 1-4  alkoxy, C 1-4  haloalkyl, C 1-4  haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino, dialkylamino or C 1-4  alkoxycarbonyl), phenyl (C 1-6 )alkyl (wherein the phenyl group may be optionally substituted by halogen, C 1-4  alkyl, C 1-4  alkoxy, C 1-4  haloalkyl, C 1-4  haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino, dialkylamino, C 1-6  alkylsulfonyl, C 1-6  alkoxycarbonyl, or two adjacent positions on the phenyl ring may be cyclised to form a 5, 6 or 7 membered carbocyclic or heterocyclic ring, itself optionally substituted with halogen), heteroaryl (C 1-6 )alkyl (wherein the heteroaryl group may be optionally substituted by halo, nitro, cyano, C 1-6  alkyl, C 1-6  haloalkyl, C 1-6  alkoxy, C 1-6  haloalkoxy, C 1-6  alkylsulfonyl, C 1-6  alkylsulfinyl, C 1-6  alkylthio, C 1-6  alkoxycarbonyl, C 1-6  alkylcarbonylamino, arylcarbonyl, or two adjacent positions on the heteroaryl system may be cyclised to form a 5, 6 or 7 membered carbocyclic or heterocyclic ring, itself optionally substituted with halogen) or heteroaryl (which may be optionally substituted by halo, nitro, cyano, C 1-6  alkyl, C 1-6  haloalkyl, C 1-6  alkoxy or C 1-6  haloalkoxy, C 1-4  alkoxycarbonyl C 1-6  alkylcarbonylamino, phenyloxycarbonylamino (wherein the phenyl group is optionally substituted by halogen, C 1-4  alkyl, C 1-4  alkoxy, C 1-4  haloalkyl, C 1-4  haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino), amino, C 1-6  alkylamino or phenylamino (wherein the phenyl group is optionally substituted halogen, C 1-4  alkyl, C 1-4  alkoxy, C 1-4  haloalkyl, C 1-4  haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino)).   
     
     
         6 . The compound according to  claim 1  wherein R 2  is hydrogen, hydroxy, C 1-6  alkyl or C 1-6  haloalkyl. 
     
     
         7 . The compound according to  claim 1  wherein R 3  is hydrogen, hydroxy, halogen, C 1-6  alkyl or C 1-6  haloalkyl and R 3a  is hydrogen or R 3  and R 3a  together form a double bond. 
     
     
         8 . The compound according to  claim 1  wherein each Ra is independently fluoro, methyl, hydroxy or two Ra groups together with the carbon atom to which they are attached form a carbonyl group and p is 0, 1 or 2. 
     
     
         9 . The compound according to  claim 1  wherein the ring 
       
         
           
           
               
               
           
         
       
       is a 6 membered aromatic ring or is a 6 membered heteroaromatic ring. 
     
     
         10 . The compound according to  claim 1  wherein the ring 
       
         
           
           
               
               
           
         
       
       is a 6 membered aromatic ring. 
     
     
         11 . An insecticidal, acaricidal or nematicidal composition comprising an insecticidally, acaricidally or nematicidally effective amount of a compound of formula I as defined in  claim 1 .