Endoparasite control agent

Abstract

An object of the present invention is to provide a novel endoparasite control agent as a parasiticide, an antiprotozoal or the like. Provided is an endoparasite control agent comprising a carboxamide derivative represented by the general formula (I): (wherein Het represents a 5- or 6-membered heterocyclic group), or a salt thereof as an active ingredient.

1 - 10 . (canceled) 
     
     
         11 . A method for controlling endoparasites, comprising orally or parenterally administering an effective amount of an endoparasite control composition comprising a compound of the general formula (I): 
       
         
           
           
               
               
           
         
       
       wherein 
       
         
           
           
               
               
           
         
       
       is any moiety selected from the group consisting of the following Het1 to Het3 and Het8 to Het17: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       wherein
 the numbers on each ring represent positions where the ring can be substituted by X and the free bond extending from each ring is a bond between Het and the carbonyl group in the general formula (I), 
 each X can be the same or different, and represents a halogen atom; a cyano group; a nitro group; an amino group; a (C 1 -C 6 ) alkyl group; a halo (C 1 -C 6 ) alkyl group; a (C 1 -C 6 ) alkoxy group; a halo (C 1 -C 6 ) alkoxy group; a halo (C 1 -C 6 ) alkylthio group; a (C 1 -C 6 ) alkylsulfinyl group; a halo (C 1 -C 6 ) alkylsulfinyl group; a (C 1 -C 6 ) alkylsulfonyl group; or a halo (C 1 -C 6 ) alkylsulfonyl group, 
 X 1  represents a halogen atom, a (C 1 -C 6 ) alkyl group; or a halo (C 1 -C 6 ) alkyl group, 
 m represents an integer of 0 to 5, 
 A represents a (C 1 -C 8 ) alkylene group; or a substituted (C 1 -C 8 ) alkylene group having one or more substituents selected from a halogen atom, a (C 1 -C 6 ) alkyl group and a (C 3 -C 6 ) cycloalkyl group, with the proviso that the (C 1 -C 8 ) alkylene group and the substituted (C 1 -C 8 ) alkylene group can be modified by incorporation, into the carbon chain, of at least one group selected from —O—, —S—, —SO—, —SO 2 — and —N(R)—, wherein R represents a hydrogen atom, a (C 1 -C 6 ) alkyl group, a (C 3 -C 6 ) cycloalkyl group, a (C 1 -C 6 ) alkylcarbonyl group or a (C 1 -C 6 ) alkoxycarbonyl group, and with the proviso that when the alkylene group or the substituted alkylene group having one or more substituents is a (C 3 -C 6 ) or (C 3 -C 8 ) alkylene group, or a (C 2 -C 6 ) or (C 2 -C 8 ) alkylene group modified by incorporation, into the carbon chain, of at least one group selected from —O—, —S—, —SO—, —SO 2 — and —N(R)—, A can form a cyclic structure that is cyclopropane, cyclobutane, cyclopentane or cyclohexane, 
 E represents a hydrogen atom; a (C 1 -C 6 ) alkyl group; a (C 3 -C 6 ) cycloalkyl group; a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; a (C 1 -C 6 ) alkylcarbonyl group; or a (C 1 -C 6 ) alkoxycarbonyl group, and 
 B represents any of the moieties represented by the following B1 to B8: 
 
       
         
           
           
               
               
           
         
         wherein each Y can be the same or different, and represents a halogen atom; a cyano group; a nitro group; a hydroxy group; a (C 1 -C 6 ) alkyl group; a halo (C 1 -C 6 ) alkyl group; a (C 2 -C 6 ) alkenyl group; a halo (C 2 -C 6 ) alkenyl group; a (C 2 -C 6 ) alkynyl group; a halo (C 2 -C 6 ) alkynyl group; a (C 1 -C 6 ) alkoxy group; a halo (C 1 -C 6 ) alkoxy group; a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkoxy group; a (C 2 -C 6 ) alkenyloxy group; a halo (C 2 -C 6 ) alkenyloxy group; a (C 2 -C 6 ) alkynyloxy group; a halo (C 2 -C 6 ) alkynyloxy group; a (C 1 -C 6 ) alkylthio group; a halo (C 1 -C 6 ) alkylthio group; a (C 1 -C 6 ) alkylsulfinyl group; a halo (C 1 -C 6 ) alkylsulfinyl group; a (C 1 -C 6 ) alkylsulfonyl group; a halo (C 1 -C 6 ) alkylsulfonyl group; a (C 1 -C 6 ) alkoxycarbonyl group; a (C 1 -C 6 ) alkoxyimino (C 1 -C 3 ) alkyl group; a (C 3 -C 30 ) trialkylsilyl group; a mono (C 1 -C 6 ) alkylsulfonylamino group; a mono halo (C 1 -C 6 ) alkylsulfonylamino group; a phenyl group; a substituted phenyl group having one or more substituents selected from group Z substituents on the ring; a phenoxy group; a substituted phenoxy group having one or more substituents selected from group Z substituents on the ring; a heterocyclic group; a substituted heterocyclic group having one or more substituents selected from group Z substituents on the ring; a heterocycloxy group; or a substituted heterocycloxy group having one or more substituents selected from group Z substituents on the ring, 
         the group Z substituents are a halogen atom; a cyano group; a nitro group; a (C 1 -C 6 ) alkyl group; a halo (C 1 -C 6 ) alkyl group; a (C 2 -C 6 ) alkenyl group; a halo (C 2 -C 6 ) alkenyl group; a (C 2 -C 6 ) alkynyl group; a halo (C 2 -C 6 ) alkynyl group; a (C 1 -C 6 ) alkoxy group; a halo (C 1 -C 6 ) alkoxy group; a (C 2 -C 6 ) alkenyloxy group; a halo (C 2 -C 6 ) alkenyloxy group; a (C 2 -C 6 ) alkynyloxy group; a halo (C 2 -C 6 ) alkynyloxy group; a (C 1 -C 6 ) alkylthio group; a halo (C 1 -C 6 ) alkylthio group; a (C 1 -C 6 ) alkylsulfinyl group; a halo (C 1 -C 6 ) alkylsulfinyl group; a (C 1 -C 6 ) alkylsulfonyl group; a halo (C 1 -C 6 ) alkylsulfonyl group; a (C 1 -C 6 ) alkoxycarbonyl group; and a (C 1 -C 6 ) alkoxyimino (C 1 -C 3 ) alkyl group, 
         Y 1  represents a (C 1 -C 6 ) alkyl group, 
         n represents an integer of 0 to 5, with the proviso that when n is an integer of 2 to 5, two adjacent Y groups can join together to form a (C 3 -0 5 ) alkylene group; a (C 3 -0 5 ) alkenylene group; a (C 2 -C 4 ) alkyleneoxy group; a (C 1 -C 3 ) alkylene dioxy group; or a halo (C 1 -C 3 ) alkylene dioxy group, and 
         the numbers on each ring represent positions where the ring can be substituted by Y and the free bond extending from each ring is a bond between A and B, or 
         a salt thereof as an active ingredient to a non-human mammal or a bird, wherein the endoparasite is helminths. 
       
     
     
         12 . The method according to  claim 11 , wherein the effective amount of the endoparasite control agent is orally or parenterally administered to a non-human mammal. 
     
     
         13 . The method according to  claim 12 , wherein the non-human mammal is a domestic animal. 
     
     
         14 . The method according to  claim 11 , wherein 
       
         
           
           
               
               
           
         
       
       is selected from the group consisting of Het8 to Het17. 
     
     
         15 . The method according to  claim 11 , wherein A is a (C 1 -C 8 ) alkylene group; or a substituted (C 1 -C 8 ) alkylene group having one or more substituents selected from a halogen atom, a (C 1 -C 6 ) alkyl group and a (C 3 -C 6 ) cycloalkyl group. 
     
     
         16 . The endoparasite control agent method according to  claim 11 , wherein B is selected from the group consisting of B5 to B8. 
     
     
         17 . The method according to  claim 14 , 
       wherein 
       
         
           
           
               
               
           
         
       
       is selected from the group consisting of Het8 to Het14,
 each X can be the same or different, and is a halogen atom; a (C 1 -C 6 ) alkyl group; or a halo (C 1 -C 6 ) alkyl group, 
 m is 1 or 2, 
 A is a (C 1 -C 8 ) alkylene group; or a (C 1 -C 8 ) alkylene group substituted by a (C 1 -C 6 ) alkyl group, 
 E is a hydrogen atom, 
 B is B1, B2 or B5, 
 each Y can be the same or different, and is a halogen atom; a (C 1 -C 6 ) alkyl group; a halo (C 1 -C 6 ) alkyl group; a phenyl group; a substituted phenyl group having one or more substituents selected from a halogen atom, a (C 1 -C 6 ) alkyl group, a halo (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group and a halo (C 1 -C 6 ) alkoxy group on the ring; a phenoxy group; a substituted phenoxy group having one or more substituents selected from a halogen atom, a (C 1 -C 6 ) alkyl group, a halo (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group and a halo (C 1 -C 6 ) alkoxy group on the ring; a pyridyl group; a substituted pyridyl group having one or more substituents selected from a halogen atom, a (C 1 -C 6 ) alkyl group, a halo (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group and a halo (C 1 -C 6 ) alkoxy group on the ring; a pyridyloxy group; or a substituted pyridyloxy group having one or more substituents selected from a halogen atom, a (C 1 -C 6 ) alkyl group, a halo (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group and a halo (C 1 -C 6 ) alkoxy group on the ring, and n is an integer of 1 to 3. 
 
     
     
         18 . The method according to  claim 14 , 
       wherein 
       
         
           
           
               
               
           
         
       
       is Het1, Het2, Het14, Het15 or Het17,
 each X can be the same or different, and is a halogen atom; a (C 1 -C 6 ) alkyl group; or a halo (C 1 -C 6 ) alkyl group, 
 m is 1 or 2, 
 A is a (C 1 -C 8 ) alkylene group; or a (C 1 -C 8 ) alkylene group substituted by a (C 1 -C 6 ) alkyl group, 
 E is a hydrogen atom, 
 B is B1, 
 each Y can be the same or different, and is a halogen atom; a (C 1 -C 6 ) alkyl group; a halo (C 1 -C 6 ) alkyl group; a phenyl group; a substituted phenyl group having one or more substituents selected from a halogen atom, a (C 1 -C 6 ) alkyl group, a halo (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group and a halo (C 1 -C 6 ) alkoxy group on the ring; a phenoxy group; a substituted phenoxy group having one or more substituents selected from a halogen atom, a (C 1 -C 6 ) alkyl group, a halo (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group and a halo (C 1 -C 6 ) alkoxy group on the ring; a pyridyl group; a substituted pyridyl group having one or more substituents selected from a halogen atom, a (C 1 -C 6 ) alkyl group, a halo (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group and a halo (C 1 -C 6 ) alkoxy group on the ring; a pyridyloxy group; or a substituted pyridyloxy group having one or more substituents selected from a halogen atom, a (C 1 -C 6 ) alkyl group, a halo (C 1 -C 6 ) alkyl group, a (C 1 -C 6 ) alkoxy group and a halo (C 1 -C 6 ) alkoxy group on the ring, and 
 n is an integer of 1 to 3.