4-(3,3-dihalo-allyloxy)phenol derivatives having pesticidal properties

Abstract

Compounds of formula wherein A 0 is a bond or a C 1 -C 6 alkylene bridge; A 1 , A 2 and A 3 are a C 1 -C 6 alkylene bridge; D is CH or N; W is, for example, O, S, SO, SO 2 , —C(═O)—O— or —O—C(═O)—; T is a bond or, for example, O, NH, S, SO or SR 2 ; Q is, for example, O, S, SO or SO 2 ; Y is, for example, O, S, SO or SO 2 ; 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 or nitro; R 4 is, for example, H, halogen, OH, SH, CN, nitro or C 1 -C 6 alkyl; R 5 is, for example, H, CN, OH, C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl; k is 1, 2 or 3 when D is nitrogen; or is 1, 2, 3 or 4 when D is CH; m is 1 or 2; E is heteroaryl which is unsubstituted or substituted—depending upon the substitutions possible on the ring—by from one to four identical or different substituents selected from R 10 ; and R 10 is, for example, halogen, CN, NO 2 , OH, SH or C 1 -C 6 alkyl; 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 or an agrochemically acceptable salt thereof, a process for the preparation of those compositions and their use, 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 other 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 C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl-C 1 -C 6 alkyl and C 1 -C 3 haloalkyl; 
       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 C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl-C 1 -C 6 alkyl and C 1 -C 3 haloalkyl; 
       D is CH or N; 
       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; 
       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 or C 1 -C 6 alkoxycarbonyl; the substituents R 4  being independent of one another when k is greater than 1; or N(R 5 ) 2  wherein the two substituents R 5  are independent of one another; 
       R 5  is H, CN, OH, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl-C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, 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, —C(═O)R 8 , —C(═S)R 8 , phenyl, benzyl; or phenyl or benzyl each of which is substituted in the aromatic ring by from one to five identical or different substituents selected from the group consisting of halogen, C 1 -C 6 alkyl, halo-C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo-C 1 -C 6 -alkoxy, hydroxy, cyano and nitro; 
       or the two substituents R 5  together form a four- to eight-membered, straight-chain or branched alkylene bridge wherein a CH 2  group may have been replaced by O, S or NR 9 , and the alkylene bridge is unsubstituted or substituted by from one to four identical or different substituents selected from C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl-C 1 -C 6 alkyl and C 1 -C 3 haloalkyl; 
       W is O, NR 6 , S, SO, SO 2 , —C(═O)—O—, —O—C(═O)—, —C(═O)—NR 7 — or —NR 7 —C(═O)—; 
       T is a bond, O, NH, NR 6 , S, SO, SO 2 , —C(═O)—O—, —O—C(═O)—, —C(═O)—NR 7 — or —NR 7 —C(═O)—; 
       Q is O, NR 6 , S, SO or SO 2 ; 
       Y is O, NR 6 , S, SO or SO 2 ; 
       R 6  and R 7  are independently of each 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 alkoxyalkyl, C 3 -C 8 cycloalkyl or benzyl; 
       R 8  is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, 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, C 3 -C 6 cycloalkyl, phenyl, benzyl; or phenyl or benzyl each of which is unsubstituted or substituted by from one to three identical or different substituents selected from halogen, 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 1 -C 6 alkoxycarbonyl, C 1 -C 3 haloalkoxycarbonyl and C 2 -C 6 haloalkenyloxy; 
       R 9  is H, C 1 -C 6 alkyl, C 1 -C 3 haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkoxyalkyl, C 3 -C 8 cycloalkyl or benzyl; 
       k is 1, 2 or 3 when D is nitrogen; or is 1, 2, 3 or 4 when D is CH; 
       m is 1 or 2; 
       E is heteroaryl which is unsubstituted or substituted—depending upon the substitutions possible on the ring—by from one to four identical or different substituents selected from R 10 ; 
       R 10  is halogen, CN, NO 2 , OH, SH, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6  hydroxyalkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl-C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 1 -C 6 alkoxy, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 haloalkoxy-C 1 -C 6 alkyl, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, 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 3 -C 6 haloalkynyloxy, C 3 -C 6 alkynyloxy-C 1 -C 6 alkyl, C 3 -C 8 -cycloalkoxy, C 3 -C 8 cycloalkyl-C 1 -C 6 alkoxy, C 3 -C 8 cycloalkoxy-C 1 -C 6 alkyl, C 3 -C 8 cycloalkoxy-C 1 -C 6 alkoxy, C 3 -C 8 cycloalkyl-C 1 -C 6 alkoxy-C 1 -C 6 alkyl, 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 cycloalkylthio, C 3 -C 6 cycloalkyl-C 1 -C 6 alkylthio, C 2 -C 6 haloalkenylthio, C 1 -C 6 haloalkylthio, 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, C 1 -C 6 alkylaminocarbonylamino, —SO—C 1 -C 6 alkyl, —SO-halo-C 1 -C 6 alkyl, —SO 2 —C 1 -C 6 alkyl, —SO 2 -halo-C 1 -C 6 alkyl, —C(═O)R 11 , phenyl or benzyl; wherein the phenyl and benzyl radicals may be unsubstituted or may carry independently of each other one to three substituents selected form the group consisting of 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 and C 2 -C 6 haloalkenyloxy; and 
       R 11  is H, OH, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl-C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 cycloalkyl-C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 2 -C 6 alkynyloxy, C 2 -C 6 haloalkynyloxy, NH 2 , NH—C 1 -C 6 alkyl, —N(C 1 -C 6 alkyl) 2 , NH-phenyl, NH-benzyl, phenoxy or benzyloxy; 
       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. 
     
   
   
       2 . A compound according to  claim 1  of formula (I) in free form. 
   
   
       3 . A compound according to  claim 1 , of formula (I), wherein X 1  and X 2  are chlorine or bromine. 
   
   
       4 . A pesticidal composition which comprises as active ingredient at least one compound according to  claim 1  of formula (I), in free form or in agrochemically acceptable salt form, and at least one adjuvant. 
   
   
       5 . A process for the preparation of a composition as described in  claim 4 , which comprises intimately mixing the active ingredient with the adjuvant(s). 
   
   
       6 . A method of controlling pests, which comprises applying a pesticidal composition as described in  claim 4  to the pests or to the locus thereof. 
   
   
       7 . (canceled)