Pesticidally active ketone and oxime derivatives

Abstract

Compounds of formula wherein A 0 , A 1 and A 2 are each independently of the others a bond or a C 1 -C 6 alkylene bridge; A 3 is a C 1 -C 6 alkylene bridge which is unsubstituted or substituted by from one to six identical or different substituents selected from halogen and C 3 -C 8 cycloalkyl; Y is, for example, O, S, SO or SO 2 ; M is O or NOR 6 , X 1 and X 2 are each independently of the other fluorine, chlorine or bromine; R 1 , R 2 and R 3 are, for example, H, halogen, OH, SH, CN, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkylcarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl or C 2 -C 6 alkynyl; Q is, for example, O, S, SO or SO 2 ; W is, for example, O, S, SO, SO 2 , —C(═O)—O— or —O—C(═O)—; T is, for example, a bond, O, S, SO, SO 2 , —C(═O)—O— or —O—C(═O)—; D is CH or N; R 4 is, for example, H, halogen, OH, SH, CN, nitro, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl; R 5 is, for example, C 1 -C 12 alkyl, C 3 -C 8 cycloalkyl or —N(R 7 ) 2 ; R 7 is H, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkylcarbonyl or formyl; k is 0, 1, 2, 3 or 4; m is 1 or 2; and q is 0, 1 or 2; and, where applicable, their possible E/Z isomers, E/Z isomeric mixtures and/or tautomers, in each case in free form or in salt form, a process for the preparation of those compounds and their use, pesticidal compositions in which the active ingredient has been selected from those compounds and agrochemically acceptable salts thereof, and a process for the preparation of those compositions and their use, to plant propagation material treated with those compositions, and a method of controlling pests.

1 . A compound of formula 
     
       
         
         
             
             
         
       
       wherein 
       A 0 , A 1  and A 2  are each independently of the others a bond or a C 1 -C 6 alkylene bridge which is unsubstituted or substituted by from one to six identical or different substituents selected from halogen and C 3 -C 8 cycloalkyl; 
       A 3  is a C 1 -C 6 alkylene bridge which is unsubstituted or substituted by from one to six identical or different substituents selected from halogen and C 3 -C 8 cycloalkyl; 
       Y is O, NR 11 , S, SO or SO 2 ; 
       M is O or NOR 6 , 
       X 1  and X 2  are each independently of the other fluorine, chlorine or bromine; 
       R 1 , R 2  and R 3  are each independently of the others H, halogen, OH, SH, CN, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkylcarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, —S(═O)—C 1 -C 6 alkyl, —S(═O) 2 —C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl or C 3 -C 6 haloalkynyloxy; the substituents R 3  being independent of one another when m is 2; 
       Q is O, NR 11 , S, SO or SO 2 ; 
       W is O, NR 11 , S, SO, SO 2 , —C(═O)—O—, —O—C(═O)—, —C(═O)—NR 11 — or —NR 11 —C(═O)—; 
       T is a bond, O, NR 11 , S, SO, 
     
     SO 2 , —C(═O)—O—, —O—C(═O)—, —C(═O)—NR 11 — or —NR 11 —C(═O)—;
 D is CH or N; 
 R 4  is H, halogen, OH, SH, CN, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkylcarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, —S(═O)—C 1 -C 6 alkyl, —S(═O) 2 —C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl, C 3 -C 6 haloalkynyloxy, NH 2 , NH(C 1 -C 6 alkyl) or N(C 1 -C 6 alkyl) 2  wherein the two alkyl groups are independent of one another; the substituents R 4  being independent of one another when k is greater than 1; 
 R 5  is C 1 -C 12 alkyl substituted by from one to five substituents selected from the group consisting of —N 3 , NO 2 , OH, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkoxy, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 3 -C 6 alkynyloxy, C 3 -C 6 haloalkynyl, C 3 -C 6 haloalkynyloxy, C 3 -C 8 cycloalkyl-C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy, —P(═O)(OC 1 -C 6 alkyl) 2 , —S(O) q —R 13 , NH 2 , NH(C 1 -C 6 alkyl), N(C 1 -C 6 alkyl) 2 wherein the two alkyl groups are independent of one another, —N(R 7 ) 2  wherein the two R 7 s are independent of one another and —NR 14 S(O)qR 15 ; 
 C 3 -C 8 cycloalkyl substituted by from one to five identical or different substituents selected from the group consisting of C 1 -C 6 alkyl, halogen, CN, NO 2 , OH, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, NH 2 , NH(C 1 -C 6 alkyl) and N(C 1 -C 6 alkyl) 2  wherein the two alkyl groups are independent of one another; 
 —N(R 7 ) 2  wherein the two R 7 s are independent of one another; 
 —C(═O)—O—R 8 ; —C(═O)—R 9 ; —C(═O)—NH—R 9 ; —C(═N—O—R 9 )R 10 ; —C(═N—NH—R 9 )R 10 ; C 2 -C 6 alkenyl; C 2 -C 6 alkynyl; heterocyclyl; or 
 —NR 14 S(O)qR 15    
 wherein the alkenyl and alkynyl radicals are unsubstituted or, depending upon the possibilities of substitution, substituted by from one to five identical or different substituents selected from the group consisting of halogen, —N 3 , CN, NO 2 , OH, C 3 -C 8 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 3 -C 6 alkynyloxy, C 3 -C 6 haloalkynyloxy, C 3 -C 8 cycloalkyl-C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyl-C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl, C 3 -C 6 haloalkynyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 haloalkoxy-C 1 -C 6 alkyl, C 2 -C 6 alkenyloxy-C 1 -C 6 alkyl, C 2 -C 6 haloalkenyloxy-C 1 -C 6 alkyl, C 3 -C 6 alkynyloxy-C 1 -C 6 alkyl, —P(═O)(OC 1 -C 6 alkyl) 2 , —S(O) q —R 13 , NH 2 , NH(C 1 -C 6 alkyl) and N(C 1 -C 6 alkyl) 2 , wherein the two alkyl groups are independent of one another; 
 and wherein the heterocyclyl radical mentioned under R 5  are unsubstituted or, depending upon the possibilities of substitution, substituted by from one to five substituents selected from halogen, CN, NO 2 , OH, SH, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl-C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 3 -C 6 alkynyloxy, C 3 -C 6 haloalkynyloxy, C 3 -C 8 cycloalkyl-C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyl-C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl, C 1 -C 6 alkylthio, C 2 -C 6 alkenylthio, C 3 -C 6 alkynylthio, C 3 -C 6 cycloalkyl-C 1 -C 6 alkylthio, C 3 -C 6 haloalkynyl, C 2 -C 6 haloalkenylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 haloalkoxy-C 1 -C 6 alkyl, C 2 -C 6 alkenyloxy-C 1 -C 6 alkyl, C 2 -C 6 haloalkenyloxy-C 1 -C 6 alkyl, C 3 -C 6 alkynyloxy-C 1 -C 6 alkyl, NH 2 , NH(C 1 -C 6 alkyl), N(C 1 -C 6 alkyl) 2  wherein the two alkyl groups are independent of one another, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 haloalkylcarbonylamino, C 1 -C 6 alkoxycarbonylamino and C 1 -C 6 alkylaminocarbonylamino; 
 or, when A 0  is a C 1 -C 6 alkylene bridge, R 5  is C 2 -C 6 alkylene bonded to one of the carbon atoms of A 0 ; 
 or, when R 4  and a group —C(═NOR 6 )R 5  are in the ortho-position relative to one another, R 4  and R 5  together form a C 2 -C 6 alkylene bridge wherein one or two CH 2  groups each independently of the other may be replaced by O, NR 12 , S or SO, and wherein the CH 2  groups are unsubstituted or mono- or di-substituted by halogen, OH, SH, CN, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy; 
 R 6  is H, C 1 -C 12 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 6 alkylcarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, aryl, heterocyclyl or benzyl, wherein the alkyl, cycloalkyl, alkenyl and alkynyl radicals are unsubstituted or, depending upon the possibilities of substitution, substituted by from one to five identical or different substituents selected from the group consisting of halogen, —N 3 , CN, NO 2 , OH, SH, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 3 -C 6 alkynyloxy, C 3 -C 6 haloalkynyloxy, C 3 -C 8 cycloalkyl-C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyl-C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl, C 1 -C 6 alkylthio, C 2 -C 6 alkenylthio, C 3 -C 6 alkynylthio, C 3 -C 6 cycloalkyl-C 1 -C 6 alkylthio, C 3 -C 6 haloalkynyl, C 2 -C 6 haloalkenylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 haloalkoxy-C 1 -C 6 alkyl, C 2 -C 6 alkenyloxy-C 1 -C 6 alkyl, C 2 -C 6 haloalkenyloxy-C 1 -C 6 alkyl, C 3 -C 6 alkynyloxy-C 1 -C 6 alkyl, NH 2 , NH(C 1 -C 6 alkyl), N(C 1 -C 6 alkyl) 2  wherein the two alkyl groups are independent of one another, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 haloalkylcarbonylamino, C 1 -C 6 alkoxycarbonylamino and C 1 -C 6 alkylaminocarbonylamino; 
 and the aryl, heterocyclyl and benzyl radicals are unsubstituted or, depending upon the possibilities of substitution, substituted by from one to five identical or different substituents selected from the group consisting of halogen, CN, NO 2 , OH, SH, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl-C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 3 -C 6 alkynyloxy, C 3 -C 6 haloalkynyloxy, C 3 -C 8 cycloalkyl-C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyl-C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl, C 1 -C 6 alkylthio, C 2 -C 6 alkenylthio, C 3 -C 6 alkynylthio, C 3 -C 6 cycloalkyl-C 1 -C 6 alkylthio, C 3 -C 6 haloalkynyl, C 2 -C 6 haloalkenylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 haloalkoxy-C 1 -C 6 alkyl, C 2 -C 6 alkenyloxy-C 1 -C 6 alkyl, C 2 -C 6 haloalkenyloxy-C 1 -C 6 alkyl, C 3 -C 6 alkynyloxy-C 1 -C 6 alkyl, NH 2 , NH(C 1 -C 6 alkyl), N(C 1 -C 6 alkyl) 2  wherein the two alkyl groups are independent of one another, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 haloalkylcarbonylamino, C 1 -C 6 alkoxycarbonylamino and C 1 -C 6 alkylaminocarbonylamino; 
 R 7  is H, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 3 -C 8 cycloalkyl, C 3 -C 8  cycloalkylcarbonyl or formyl; 
 R 8  is H, C 1 -C 12 alkyl substituted by from one to five identical or different substituents selected from halogen, —N 3 , CN, NO 2 , OH, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, NH 2 , NH(C 1 -C 6 alkyl), N(C 1 -C 6 alkyl) 2  wherein the two alkyl groups are independent of one another and C 1 -C 6 alkylcarbonylamino; C 3 -C 8 cycloalkyl, C 1 -C 6 alkylcarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, aryl, heterocyclyl or benzyl, wherein the aryl, heterocyclyl and benzyl radicals are unsubstituted or, depending upon the possibilities of substitution, substituted by from one to five substituents selected from the group consisting of halogen, CN, NO 2 , OH, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 3 -C 6 alkynyloxy, C 3 -C 6 haloalkynyloxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio, C 2 -C 6 alkenylthio, C 3 -C 6 alkynylthio, C 1 -C 6 alkylthio, C 3 -C 6 haloalkynyl, C 1 -C 6 haloalkylthio, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, NH 2 , NH(C 1 -C 6 alkyl), N(C 1 -C 6 alkyl) 2 , C 1 -C 6 alkylcarbonylamino, C 1 -C 6 haloalkylcarbonylamino, C 1 -C 6 alkoxycarbonylamino and C 1 -C 6 alkylaminocarbonylamino; 
 R 9  is H, C 1 -C 12 alkyl unsubstituted or substituted by from one to five identical or different substituents selected from halogen, CN, NO 2 , OH, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, NH 2 , NH(C 1 -C 6 alkyl), N(C 1 -C 6 alkyl) 2  wherein the two alkyl groups are independent of one another and C 1 -C 6 alkylcarbonylamino; C 3 -C 8 cycloalkyl, C 1 -C 6 alkylcarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, aryl, heterocyclyl or benzyl, wherein the aryl, heterocyclyl and benzyl radicals are unsubstituted or, depending upon the possibilities of substitution, substituted by from one to five substituents selected from the group consisting of halogen, CN, NO 2 , OH, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 3 -C 6 alkynyloxy, C 3 -C 6 haloalkynyloxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio, C 2 -C 6 alkenylthio, C 3 -C 6 alkynylthio, C 1 -C 6 alkylthio, C 3 -C 6 haloalkynyl, C 1 -C 6 haloalkylthio, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, NH 2 , NH(C 1 -C 6 alkyl), N(C 1 -C 6 alkyl) 2  wherein the two alkyl groups are independent of one another, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 haloalkylcarbonylamino, C 1 -C 6 alkoxycarbonylamino and C 1 -C 6 alkylaminocarbonylamino; 
 R 10  is H, C 1 -C 12 alkyl unsubstituted or substituted by from one to five identical or different substituents selected from halogen, CN, NO 2 , OH, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, NH 2 , NH(C 1 -C 6 alkyl), N(C 1 -C 6 alkyl) 2  and C 1 -C 6 alkylcarbonylamino; C 3 -C 8 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, aryl, heterocyclyl or benzyl, wherein the aryl, heterocyclyl and benzyl radicals are unsubstituted or, depending upon the possibilities of substitution, substituted by from one to five identical or different substituents selected from the group consisting of halogen, CN, NO 2 , OH, SH, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyl-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, NH 2 , NH(C 1 -C 6 alkyl), N(C 1 -C 6 alkyl) 2  wherein the two alkyl groups are independent of one another, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 haloalkylcarbonylamino, C 1 -C 6 alkoxycarbonylamino and C 1 -C 6 alkylaminocarbonylamino; 
 R 11  and R 12  are each independently of the other H, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl-C 1 -C 6 alkyl or C 3 -C 8 cycloalkylcarbonyl; 
 R 13  is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 alkynyl or C 1 -C 6 haloalkyl; 
 R 14  is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 alkynyl or C 1 -C 6 haloalkyl; 
 R 15  is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 alkynyl or C 1 -C 6 haloalkyl; 
 k is 0, 1, 2, 3 or 4; 
 m is 1 or 2; and 
 q is 0, 1 or 2; 
 or, where applicable, a possible E/Z isomer, E/Z isomeric mixture and/or tautomer thereof, in each case in free form or in salt form. 
 
   
   
       2 . The compound according to  claim 1  wherein M is NOR 6 . 
   
   
       3 . The compound according to  claim 1  wherein M is O. 
   
   
       4 . The compound according to  claim 1  in free form. 
   
   
       5 . A compound according to  claim 1  wherein X 1  and X 2  are chlorine or bromine. 
   
   
       6 . A compound according to  claim 1  wherein D is CH. 
   
   
       7 . A compound according to  claim 1  wherein A 3  is straight-chain alkylene bridge. 
   
   
       8 . A compound according to  claim 1  wherein R 5  is C 1 -C 12 alkoxy-C 1 -C 12 alkyl. 
   
   
       9 . A compound according to  claim 1  wherein R 5  is heterocyclyl. 
   
   
       10 . A pesticidal composition which comprises as active ingredient at least one compound defined in  claim 1 , in free form or in agrochemically acceptable salt form, and at least one adjuvant. 
   
   
       11 . A method of controlling pests which comprises applying a pesticidal composition as defined in  claim 10  to the pests or to the locus thereof.