Aminobenzamide Derivatives as Useful Agents for Controlling Animal Parasistes

Abstract

The invention relates to a composition comprising at least one aminobenzamide compound or a salt thereof for controlling animal parasites, veterinary pharmaceutical compositions comprising at least one aminobenzamide of formula (I) for preventing infection with diseases transmitted through parasites, its use for the preparation of a veterinary pharmaceutical for controlling animal parasites, and a method for preventing infection with diseases transmitted through parasites.

1 . Aminobenzamide derivative of formula (I), or a salt thereof 
       
         
           
           
               
               
           
         
       
       wherein
 A 1 , A 2 , A 3  and A 4  each represent independent from each other C—X, N or N═O; 
 X represents independent from each other a hydrogen atom, a halogen atom, a hydroxy group, a C 1 -C 6  alkyl group or a trifluoromethyl group; 
 B 1  and B 2  each represent independent from each other an oxygen atom or a sulfur atom; 
 R 1  and R 2  respectively represent independent from each other a hydrogen atom, a C 1 -C 6  alkyl group, a C 1 -C 6  haloalkyl group, a C 1 -C 6  alkoxy group, a C 1 -C 6  haloalkoxy group, a C 1 -C 6  alkylthio group, a C 1 -C 6  haloalkylthio group, a C 1 -C 6  alkylcarbonyl group, a C 1 -C 6  haloalkylcarbonyl group; or represents a phenyl group or a benzyl group optionally substituted with at least one group selected from the group consisting of C 1 -C 6  alkyl, C 1 -C 6  alkoxy, C 1 -C 6  alkylthio, C 1 -C 6  alkylsulfinyl, C 1 -C 6  alkylsulfonyl, C 1 -C 6  haloalkyl, C 1 -C 6  haloalkoxy, C 1 -C 6  haloalkylthio, C 1 -C 6  haloalkylsulfinyl, C 1 -C 6  haloalkylsulfonyl, nitro, hydroxy, and halogen; or pyridyl, pyrazolyl, thienyl, furyl, isoxazolyl, thiadiazolyl or pyridylmethyl, pyrazolylmethyl, thienylmethyl, furylmethyl, isoxazolylmethyl, or thiadiazolylmethyl optionally substituted with at least one group selected from the group consisting of C 1 -C 6  alkyl, C 1 -C 6  alkoxy, C 1 -C 6  alkylthio, C 1 -C 6  alkylsulfinyl, C 1 -C 6  alkylsulfonyl, C 1 -C 6  haloalkyl, C 1 -C 6  haloalkoxy, C 1 -C 6  haloalkylthio, C 1 -C 6  haloalkylsulfinyl, C 1 -C 6  haloalkylsulfonyl, nitro, hydroxy, and halogen; 
 Q represents L or Y—R 6    
 with 
 Y representing oxygen, sulfur, amino, C 1 -C 4  aminoalkyl; and 
 R 6  representing a C 1 -C 6  alkyl group, a C 1 -C 6  haloalkyl group, a C 2 -C 6  alkenyl group, a C 2 -C 6  haloalkenyl group, a C 2 -C 6  allynyl group, a C 2 -C 6  haloalkynyl group, a C 3 -C8 cycloalkyl group or a C 3 -C8 halocycloalkyl group; or
 -E 1 -Z 1 —R 7  (wherein E 1  represents a C 1 -C 4  alkylene group, a C 2 -C 4  alkenylene group, a C 3 -C 4  alkynylene group, a C 1 -C 4  haloalkylene group, a C 2 -C 4  haloalkenylene group or a C 3 -C 4  haloalkynylene group, R 7  represents a hydrogen atom, a C 1 -C 6  alkyl group, a C 2 -C 6  alkenyl group, a C 2 -C 6  alkynyl group, a C 1 -C 6  haloalkyl group, a C 2 -C 6  haloalkenyl group or a C 2 -C 6  haloalkynyl group, and Z 1  represents —O—, —S—, —SO—, —SO 2 —, —C(═O)—, —C(═O)O—, —OC(═O)—, —N(R 8 )—, —C(═O)N(R 8 )— or —N(R 8 )C(═O)—); or 
 -E 2 —R 9  (wherein E 2  represents a C 1 -C 4  alkylene group, a C 2 -C 4  alkenylene group, a C 3 -C 4  alkenylene group, a C 1 -C 4  haloalkylene group, a C 2 -C 4  haloalkenylene group or a C 3 -C 4  haloalkynylene group; and R 9  represents a C 3 -C 8  cycloalkyl group, a C 3 -C 8  halocycloalkyl group, a cyano group, a nitro group, a hydroxy group, a phenyl group, or a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C 1 -C 6  alkyl group, a C 1 -C 6  haloalkyl group, a C 1 -C 6  alkoxy group, a C 1 -C 6  haloalkoxy group, a C 1 -C 6  alkylthio group, a C 1 -C 6  haloalkylthio group, a C 1 -C 6  alkylsulfinyl group, a C 1 -C 6  haloalkylsulfinyl group, a C 1 -C 6  alkylsulfonyl group, a C 1 -C 6  haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxy group, a C 1 -C 4  alkylcarbonyl group, a C 1 -C 4  haloalkylcarbonyl group, a C 1 -C 4  alkylcarbonyloxy group and a C 1 -C 4  alkoxycarbonyl group, or a pyridyl group, or a substituted pyridyl group having one or more substituents which are selected from a halogen atom, a C 1 -C 6  haloalkyl group and a C 1 -C 6  haloalkoxy group, a thienyl group or a tetrahydrofuran group); 
 
 L represents a phenyl group; or
 a heterocyclyl group; or 
 hydrogen, a C 1 -C 6  alkyl group, a C 2 -C 6  alkenyl group, a C 2 -C 6  alkynyl group, a C 3 -C 8  cycloalkyl group, a C 3 -C 8  cycloalkenyl group, a C 1 -C 6  aldehyd group, a C 1 -C 6  iminoaldehyd group, a C 1 -C 6  alkoxyiminoaldehyd group, a C 1 -C 6  alkoxyimino-C 1 -C 6 -alkyl group, a C 1 -C 6  alkoxy group, a C 1 -C 6  alkylthio group, a C 1 -C 6  haloalkylthio group, a C 1 -C 6  alkylsulfinyl group, and a C 1 -C 6  alkylsulfonyl group; 
 
 
       wherein the above-mentioned residues are each optionally substituted with a halogen atom, a C 1 -C 4  alkyl group, a C 1 -C 4  haloalkyl group, a C 2 -C 4  alkenyl group, a C 2 -C 4  haloalkenyl group, a C 2 -C 4  alkynyl group, a C 2 -C 4  haloalkynyl group, a C 3 -C 6  cycloalkyl group, a C 3 -C 6  halocycloalkyl group, a C 1 -C 3  alkoxy group, a C 1 -C 3  haloalkoxy group, a C 1 -C 3  alkylthio group, a C 1 -C 3  haloalkylthio group, a C 1 -C 3  alkylsulfinyl group, a C 1 -C 3  haloalkylsulfinyl group, a C 1 -C 3  alkylsulfonyl group, a C 1 -C 3  haloalkylsulfonyl group, a C 1 -C 4  alkylamino group, a di-C 1 -C 4  alkylamino group, a cyano group, a nitro group, a hydroxy group, a C 1 -C 4  alkylcarbonyl group, a C 1 -C 4  alkylcarbonyloxy group, a C 1 -C 4  alkoxycarbonyl group, an acetylamino group, a phenyl group, and a pyridyl group;
 W represents a phenyl group, or a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C 1 -C 4  alkyl group, a C 1 -C 4  haloalkyl group, C 1 -C 4  haloalkyl C 1 -C 4  alkoxy group, C 1 -C 4  haloalkyl C 1 -C 4  haloalkoxy group, a C 1 -C 4  alkoxy group, a C 1 -C 4  haloalkoxy group, a C 1 -C 3  alkylthio group, a C 1 -C 3  haloalkylthio group, a C 1 -C 3  alkylsulfinyl group, a C 1 -C 3  haloalkylsulfinyl group, a C 1 -C 3  alkylsulfonyl group, a C 1 -C 3  haloalkylsulfonyl group, a cyano group, a carbony-C 1 -C 4 -alkyl group, a carbony-C 1 -C 4 -haloalkyl group; or a SF 5  group; 
 
       for preventing infection with diseases transmitted through parasites. 
     
     
         2 . Aminobenzamide derivative of formula (I-1), or a salt thereof 
       
         
           
           
               
               
           
         
         X represents a hydrogen atom, a halogen atom, a hydroxy group, a C 1 -C 6  alkyl group or a trifluoromethyl group; 
         R 1  represents a hydrogen atom, a C 1 -C 6  alkyl group a C 1 -C 6  haloalkyl group, a C 1 -C 6  alkoxy group, a C 1 -C 6  haloalkoxy group, a C 1 -C 6  alkylthio group, a C 1 -C 6  haloalkylthio group, a C 1 -C 6  alkylcarbonyl group, a C 1 -C 6  haloalkylcarbonyl group or represents phenyl or benzyl optionally substituted with at least one group selected from the group consisting of C 1 -C 6  alkyl, C 1 -C 6  alkoxy, C 1 -C 6  alkylthio, C 1 -C 6  alkylsulfinyl, C 1 -C 6  alkylsulfonyl, C 1 -C 6  haloalkyl, C 1 -C 6  haloalkoxy, C 1 -C 6  haloalkylthio, C 1 -C 6  haloalkylsulfinyl, C 1 -C 6  haloalkylsulfonyl, nitro, hydroxy, and halogen; or pyridyl, pyrazolyl, thienyl, furyl, isoxazolyl, thiadiazolyl or pyridylmethyl, pyrazolylmethyl, thienylmethyl, furylmethyl, isoxazolylmethyl, or thiadiazolylmethyl optionally substituted with at least one group selected from the group consisting of C 1 -C 6  alkyl, C 1 -C 6  alkoxy, C 1 -C 6  alkylthio, C 1 -C 6  alkylsulfinyl, C 1 -C 6  alkylsulfonyl, C 1 -C 6  haloalkyl, C 1 -C 6  haloalkoxy, C 1 -C 6  haloalkylthio, C 1 -C 6  haloalkylsulfinyl, C 1 -C 6  haloalkylsulfonyl, nitro, hydroxy, and halogen 
         R 3  and R 5  represents independent from each other a halogen atom, a C 1 -C 4  alkyl group, a C 1 -C 4  haloalkyl group, a C 1 -C 4  alkoxy group, a C 1 -C 4  haloalkoxy group, C 1 -C 3  alkylthio group, a C 1 -C 3  haloalkylthio group, a C 1 -C 3  alkylsulfinyl group, a C 1 -C 3  haloalkylsulfinyl group, a C 1 -C 3  alkylsulfonyl group, a C 1 -C 3  haloalkylsulfonyl group or a cyano group; 
         R 4  represents C 1 -C 4  alkyl group, a C 1 -C 4  haloalkyl group, C 1 -C 4  haloalkyl C 1 -C 4  alkoxy group, C 1 -C 4  haloalkyl C 1 -C 4  haloalkoxy group, a C 1 -C 4  alkoxy group, a C 1 -C 4  haloalkoxy group, a C 1 -C 3  alkylthio group, a C 1 -C 3  haloalkylthio group, a C 1 -C 3  alkylsulfinyl group, a C 1 -C 3  haloalkylsulfinyl group, a C 1 -C 3  alkylsulfonyl group, a C 1 -C 3  haloalkylsulfonyl group or a SF 5  group; 
         L represents a phenyl group, or a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C 1 -C 4  alkyl group, a C 1 -C 4  haloalkyl group, a C 2 -C 4  alkenyl group, a C 2 -C 4  haloalkenyl group, a C 2 -C 4  alkynyl group, a C 2 -C 4  haloalkynyl group, a C 3 -C 6  cycloalkyl group, a C 3 -C 6  halocycloalkyl group, a C 1 -C 3  alkoxy group, a C 1 -C 3  haloalkoxy group, a C 1 -C 3  alkylthio group, a C 1 -C 3  haloalkylthio group, a C 1 -C 3  alkylsulfinyl group, a C 1 -C 3  haloalkylsulfinyl group, a C 1 -C 3  alkylsulfonyl group, a C 1 -C 3  haloalkylsulfonyl group, a C 1 -C 4  alkylamino group, a di-C 1 -C 4  alkylamino group, a cyano group, a nitro group, a hydroxy group, a C 1 -C 4  alkylcarbonyl group, a C 1 -C 4  alkylcarbonyloxy group, a C 1 -C 4  alkoxycarbonyl group, an acetylamino group and a phenyl group; or a pyridyl group; or a pyridyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C 1 -C 4  alkyl group, a C 1 -C 4  haloalkyl group, a C 2 -C 4  alkenyl group, a C 2 -C 4  haloalkenyl group, a C 2 -C 4  alkynyl group, a C 2 -C 4  haloalkynyl group, a C 3 -C 6  cycloalkyl group, a C 3 -C 6  halocycloalkyl group, a C 1 -C 3  alkoxy group, a C 1 -C 3  haloalkoxy group, a C 1 -C 3  alkylthio group, a C 1 -C 3  haloalkylthio group, a C 1 -C 3  alkylsulfinyl group, a C 1 -C 3  haloalkylsulfinyl group, a C 1 -C 3  alkylsulfonyl group, a C 1 -C 3  haloalkylsulfonyl group, a C 1 -C 4  alkylamino group, a di-C 1 -C 4  alkylamino group, a cyano group, a nitro group, a hydroxy group, a C 1 -C 4  alkylcarbonyl group, a C 1 -C 4  alkylcarbonyloxy group, a C 1 -C 4  alkoxycarbonyl group, an acetylamino group and a phenyl group; or
 hydrogen, a C 1 -C 4  alkyl group, a C 1 -C 4  haloalkyl group, a C 2 -C 4  alkenyl group, a C 2 -C 4  haloalkenyl group, a C 2 -C 4  alkynyl group, a C 2 -C 4  haloalkynyl group, a C 3 -C 6  cycloalkyl group, a C 3 -C 6  halocycloalkyl group, a C 1 -C 3  alkoxy group, a C 1 -C 3  haloalkoxy group, a C 1 -C 3  alkylthio group, a C 1 -C 3  haloalkylthio group, a C 1 -C 3  alkylsulfinyl group, a C 1 -C 3  haloalkylsulfinyl group, a C 1 -C 3  alkylsulfonyl group and a C 1 -C 3  haloalkylsulfonyl group; or 
 a C 1 -C 4  alkyl group, a C 1 -C 4  haloalkyl group, a C 2 -C 4  alkenyl group, a C 2 -C 4  haloalkenyl group, a C 2 -C 4  alkynyl group, a C 2 -C 4  haloalkynyl group, a C 3 -C 6  cycloalkyl group, a C 3 -C 6  halocycloalkyl group, a C 1 -C 3  alkoxy group, a C 1 -C 3  haloalkoxy group, a C 1 -C 3 -alkylthio group, a C 1 -C 3  haloalkylthio group, a C 1 -C 3  alkylsulfinyl group, a C 1 -C 3  haloalkylsulfinyl group, a C 1 -C 3  alkylsulfonyl group and a C 1 -C 3  haloalkylsulfonyl group, each substituted with phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C 1 -C 4  alkyl group, a C 1 -C 4  haloalkyl group, a C 2 -C 4  alkenyl group, a C 2 -C 4  haloalkenyl group, a C 2 -C 4  alkynyl group, a C 2 -C 4  haloalkynyl group, a C 3 -C 6  cycloalkyl group, a C 3 -C 6  halocycloalkyl group, a C 1 -C 3  alkoxy group, a C 1 -C 3  haloalkoxy group, a C 1 -C 3  alkylthio group, a C 1 -C 3  haloalkylthio group, a C 1 -C 3  alkylsulfinyl group, a C 1 -C 3  haloalkylsulfinyl group, a C 1 -C 3  alkylsulfonyl group, a C 1 -C 3  haloalkylsulfonyl group, a C 1 -C 4  alkylamino group, a di-C 1 -C 4  alkylamino group, a cyano group, a nitro group, a hydroxy group, a C 1 -C 4  alkylcarbonyl group, a C 1 -C 4  alkylcarbonyloxy group, a C 1 -C 4  alkoxycarbonyl group, an acetylamino group and a phenyl group; or a pyridyl 
 
       
       for preventing infection with diseases transmitted through parasites. 
     
     
         3 . Aminobenzamide derivative of formula (I-2), or a salt thereof 
       
         
           
           
               
               
           
         
         X represents a hydrogen atom, a halogen atom, a hydroxy group, a C 1 -C 3  alkyl group or a trifluoromethyl group; 
         Y represents oxygen, sulfur, amino, C 1 -C 4  aminoalkyl; 
         R 1  represents a hydrogen atom, a C 1 -C 6  alkyl group, a C 1 -C 6  haloalkyl group, a C 1 -C 6  alkoxy group, a C 1 -C 6  haloalkoxy group, a C 1 -C 6  alkylthio group, a C 1 -C 6  haloalkylthio group, a C 1 -C 6  alkylcarbonyl group, a C 1 -C 6  haloalkylcarbonyl group; or represents a phenyl group or a benzyl group optionally substituted with at least one group selected from the group consisting of C 1 -C 6  alkyl, C 1 -C 6  alkoxy, C 1 -C 6  alkylthio, C 1 -C 6  alkylsulfinyl, C 1 -C 6  alkylsulfonyl, C 1 -C 6  haloalkyl, C 1 -C 6  haloalkoxy, C 1 -C 6  haloalkylthio, C 1 -C 6  haloalkylsulfinyl, C 1 -C 6  haloalkylsulfonyl, nitro, hydroxy, and halogen; or pyridyl, pyrazolyl, thienyl, furyl, isoxazolyl, thiadiazolyl or pyridylmethyl, pyrazolylmethyl, thienylmethyl, furylmethyl, isoxazolylmethyl, or thiadiazolylmethyl optionally substituted with at least one group selected from the group consisting of C 1 -C 6  alkyl, C 1 -C 6  alkoxy, C 1 -C 6  alkylthio, C 1 -C 6  alkylsulfinyl, C 1 -C 6  alkylsulfonyl, C 1 -C 6  haloalkyl, C 1 -C 6  haloalkoxy, C 1 -C 6  haloalkylthio, C 1 -C 6  haloalkylsulfinyl, C 1 -C 6  haloalkylsulfonyl, nitro, hydroxy, and halogen; 
         R 3  and R 5  represents independent from each other a halogen atom, a C 1 -C 4  alkyl group, a C 1 -C 4  haloalkyl group, a C 1 -C 4  alkoxy group, a C 1 -C 4  haloalkoxy group, C 1 -C 3  alkylthio group, a C 1 -C 3  haloalkylthio group, a C 1 -C 3  alkylsulfinyl group, a C 1 -C 3  haloalkylsulfinyl group, a C 1 -C 3  alkylsulfonyl group, a C 1 -C 3  haloalkylsulfonyl group or a cyano group; 
         R 4  represents C 1 -C 4  alkyl group, a C 1 -C 4  haloalkyl group, C 1 -C 4  haloalkyl C 1 -C 4  alkoxy group, C 1 -C 4  haloalkyl C 1 -C 4  haloalkoxy group, a C 1 -C 4  alkoxy group, a C 1 -C 4  haloalkoxy group, a C 1 -C 3  alkylthio group, a C 1 -C 3  haloalkylthio group, a C 1 -C 3  alkylsulfinyl group, a C 1 -C 3  haloalkylsulfinyl group, a C 1 -C 3  alkylsulfonyl group, a C 1 -C 3  haloalkylsulfonyl group or a SF 5  group; 
         R 6  representing a C 1 -C 6  alkyl group, a C 1 -C 6  haloalkyl group, a C 2 -C 6  alkenyl group, a C 2 -C 6  haloalkenyl group, a C 2 -C 6  alkynyl group, a C 2 -C 6  haloalkynyl group, a C 3 -C8 cycloalkyl group or a C 3 -C8 halocycloalkyl group; or
 -E 1 -Z 1 —R 7  (wherein E 1  represents a C 1 -C 4  alkylene group, a C 2 -C 4  alkenylene group, a C 3 -C 4  alkynylene group, a C 1 -C 4  haloalkylene group, a C 2 -C 4  haloalkenylene group or a C 3 -C 4  haloalkynylene group, R 7  represents a hydrogen atom, a C 1 -C 6  alkyl group, a C 2 -C 6  alkenyl group, a C 2 -C 6  alkynyl group, a C 1 -C 6  haloalkyl group, a C 2 -C 6  haloalkenyl group or a C 2 -C 6  haloalkynyl group, and Z 1  represents —O—, —S—, —SO—, —SO 2 —, —C(═O)—, —C(═O)O—, —OC(═O)—, —N(R 8 )—, —C(═O)N(R 8 )— or —N(R 8 )C(═O)—); or 
 -E 2 —R 9  (wherein E 2  represents a C 1 -C 4  alkylene group, a C 2 -C 4  alkenylene group, a C 3 -C 4  alkynylene group, a C 1 -C 4  haloalkylene group, a C 2 -C 4  haloalkenylene group or a C 3 -C 4  haloalkynylene group; and R 9  represents a C 3 -C 8  cycloalkyl group, a C 3 -C 8  halocycloalkyl group, a cyano group, a nitro group, a hydroxy group, a phenyl group, or a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C 1 -C 6  alkyl group, a C 1 -C 6  haloalkyl group, a C 1 -C 6  alkoxy group, a C 1 -C 6  haloalkoxy group, a C 1 -C 6  alkylthio group, a C 1 -C 6  haloalkylthio group, a C 1 -C 6  alkylsulfinyl group, a C 1 -C 6  haloalkylsulfinyl group, a C 1 -C 6  alkylsulfonyl group, a C 1 -C 6  haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxy group, a C 1 -C 4  alkylcarbonyl group, a C 1 -C 4  haloalkylcarbonyl group, a C 1 -C 4  alkylcarbonyloxy group and a C 1 -C 4  alkoxycarbonyl group, or a pyridyl group, or a substituted pyridyl group having one or more substituents which are selected from a halogen atom, a C 1 -C 6  haloalkyl group and a C 1 -C 6  haloalkoxy group, a thienyl group or a tetrahydrofuran group); 
 
       
       for preventing infection with diseases transmitted through parasites. 
     
     
         4 . Pharmaceutical composition, comprising at least one aminobenzamide derivative of formulas (I), (I-1) or (I-2), or a salt thereof for preventing infection with diseases transmitted through parasites. 
     
     
         5 . Use of the aminobenzamide derivative as defined in any of  claims 1  to  3  or of a composition as defined in  claim 4  for controlling parasites. 
     
     
         6 . Use of the aminobenzamide derivative as defined in any of  claims 1  to  3  for the preparation of a composition for controlling parasites. 
     
     
         7 . Use according to  claim 6  wherein the parasites are acari. 
     
     
         8 . Use according to  claim 7  wherein the acari are selected from the group:  Amblyomma americanum, Dermacentor variabilis, Dermacentor reticulatus, Rhipicephalus sanguineus, Rhipicephalus decoloratus.    
     
     
         9 . Aminobenzamide derivative as defined in any of  claims 1  to  3  for the use in controlling parasites.