Endoparasite control agent

Abstract

The present invention is intended to provide a novel parasiticide, antiprotozoal or other endoparasite control agents which are effective for controlling animal endoparasites that have been impossible to control by conventional ones. Provided is an endoparasite control agent comprising, as an active ingredient, a carboxamide derivative represented by the general formula (I): or a salt thereof.

1 - 11 . (canceled) 
     
     
         12 . A method for controlling endoparasites, comprising orally or parenterally administering, to a mammal or a bird, an effective amount of an endoparasite control agent comprising, as an active ingredient, a carboxamide derivative represented by the general formula (I): 
       
         
           
           
               
               
           
         
         wherein 
         A represents a nitrogen atom or a C—Y 5  group (wherein Y 5  is a hydrogen atom or a (C 1 -C 6 ) alkyl group), 
         X 1  and X 2  may be the same or different, and each represent 
       
       (a1) a hydrogen atom; 
       (a2) a halogen atom; p 0  (a3) a (C 1 -C 6 ) alkyl group; 
       (a4) a halo (C 1 -C 6 ) alkyl group; 
       (a5) a (C 1 -C 6 ) alkoxy group; or 
       (a6) a halo (C 1 -C 6 ) alkoxy group,
 R 1  and R 2  may be the same or different, and are selected from the group consisting of 
 
       (b1) a hydrogen atom; 
       (b2) a halogen atom; 
       (b3) a (C 1 -C 6 ) alkyl group; 
       (b4) a (C 1 -C 6 ) alkoxy group; and 
       (b5) a halo (C 1 -C 6 ) alkyl group, or optionally 
       (b6) R 1  and R 2  together with the carbon atom bound to R 1  and R 2  form a (C 3 -C 6 ) cycloalkane,
 R 3  and R 4  may be the same or different, and are selected from the group consisting of 
 
       (c1) a hydrogen atom; 
       (c2) a halogen atom; 
       (c3) a (C 1 -C 6 ) alkyl group; 
       (c4) a (C 1 -C 6 ) alkoxy group; and 
       (c5) a halo (C 1 -C 6 ) alkyl group; or optionally 
       (c6) R 3  and R 4  together with the carbon atom bound to R 3  and R 4  form a (C 3 -C 6 ) cycloalkane,
 Y 1  represents 
 
       (d1) a hydrogen atom; 
       (d2) a halogen atom; 
       (d3) a (C 1 -C 6 ) alkyl group; 
       (d4) a halo (C 1 -C 6 ) alkyl group; 
       (d5) a (C 1 -C 6 ) alkoxy group; or 
       (d6) a halo (C 1 -C 6 ) alkoxy group,
 Y 2  and Y 4  may be the same or different, and each represent 
 
       (e1) a hydrogen atom; 
       (e2) a halogen atom; 
       (e3) a (C 1 -C 6 ) alkyl group; 
       (e4) a halo (C 1 -C 6 ) alkyl group; 
       (e5) a (C 1 -C 6 ) alkoxy group; or 
       (e6) a halo (C 1 -C 6 ) alkoxy group, and
 Y 3  represents 
 
       (f1) a phenyl group; 
       (f2) a phenyl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group; 
       (f3) a phenoxy group; 
       (f4) a phenoxy group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group; 
       (f5) a pyridyl group; 
       (f6) a pyridyl group having, on the ring, 1 to 4 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group; 
       (f7) a pyridyloxy group; 
       (f8) a pyridyloxy group having, on the ring, 1 to 4 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group; 
       (f9) a pyrimidyloxy group; 
       (f10) a pyrimidyloxy group having, on the ring, 1 to 3 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group; 
       (f11) a pyrazyloxy group; 
       (f12) a pyrazyloxy group having, on the ring, 1 to 3 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group; 
       (f13) a pyrazolyloxy group; 
       (f14) a pyrazolyloxy group having, on the ring, 1 to 3 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group, (g) a halo (C 1 -C 6 ) alkoxy group and (h) a formyl group; 
       (f15) a quinolyloxy group; 
       (f16) a quinolyloxy group having, on the ring, 1 to 6 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group; 
       (f17) a quinoxalyloxy group; 
       (f18) a quinoxalyloxy group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group; 
       (f19) a benzoxazolyloxy group; 
       (f20) a benzoxazolyloxy group having, on the ring, 1 to 4 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group; 
       (f21) a benzothiazolyloxy group; or 
       (f22) a benzothiazolyloxy group having, on the ring, 1 to 4 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group}, or a salt thereof. 
     
     
         13 . The method according to  claim 12 , wherein the endoparasite control agent is orally or parenterally administered to a non-human mammal. 
     
     
         14 . The method according to  claim 13 , wherein the non-human mammal is a domestic animal. 
     
     
         15 . The method according to  claim 12 , wherein the mammal is a human. 
     
     
         16 . The method according to  claim 12 , wherein the mammal is a non-human mammal. 
     
     
         17 . The method according to  claim 12 , wherein
 A represents a nitrogen atom or a C—H group,   X 1  and X 2  may be the same or different, and each represent   
       (a1) a hydrogen atom; 
       (a2) a halogen atom; or 
       (a4) a halo (C 1 -C 6 ) alkyl group, 
       R 1  and R 2  each represent (b1) a hydrogen atom, 
       R 3  and R 4  may be the same or different, and are selected from the group consisting of 
       (c1) a hydrogen atom; 
       (c3) a (C 1 -C 6 ) alkyl group; and 
       (c4) a (C 1 -C 6 ) alkoxy group, or optionally 
       (c6) R 3  and R 4  together with the carbon atom bound to R 3  and R 4  form a (C 3 -C 6 ) cycloalkane,
 Y 1  represents (d2) a halogen atom, 
 Y 2  and Y 4  each represent (e1) a hydrogen atom, and 
 Y 3  is selected from the group consisting of 
 
       (f1) a phenyl group; 
       (f2) a phenyl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group; 
       (f3) a phenoxy group; 
       (f4) a phenoxy group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group; 
       (f5) a pyridyl group; 
       (f7) a pyridyloxy group; 
       (f8) a pyridyloxy group having, on the ring, 1 to 4 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group; 
       (f10) a pyrimidyloxy group having, on the ring, 1 to 3 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group; 
       (f11) a pyrazyioxy group; 
       (f12) a pyrazyloxy group having, on the ring, 1 to 3 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group; 
       (f14) a pyrazolyloxy group having, on the ring, 1 to 3 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group, (g) a halo (C 1 -C 6 ) alkoxy group and (h) a formyl group; 
       (f15) a quinolyloxy group; 
       (f17) a quinoxalyloxy group; 
       (f19) a benzoxazolyloxy group; 
       (f21) a benzothiazolyloxy group; and 
       (f22) a benzothiazolyloxy group having, on the ring, 1 to 4 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group. 
     
     
         18 . The method according to  claim 12 , wherein
 A represents a C—H group,   X 1  and X 2  may be the same or different, and are selected from the group consisting of   
       (a1) a hydrogen atom; 
       (a2) a halogen atom; and 
       (a4) a halo (C 1 -C 6 ) alkyl group,
 R 1  and R 2  each represent (b1) a hydrogen atom, 
 R 3  and R 4  may be the same or different, and are selected from the group consisting of 
 
       (c1) a hydrogen atom; 
       (c3) a (C 1 -C 6 ) alkyl group; and 
       (c4) a (C 1 -C 6 ) alkoxy group, or optionally 
       (c6) R 3  and R 4  together with the carbon atom bound to R 3  and R 4  form a (C 3 -C 6 ) cycloalkane,
 Y 1  represents (d2) a halogen atom, 
 Y 2  and Y 4  each represent (e1) a hydrogen atom, and 
 Y 3  is selected from the group consisting of 
 
       (f1) a phenyl group; 
       (f2) a phenyl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group; 
       (f3) a phenoxy group; 
       (f4) a phenoxy group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group; 
       (f5) a pyridyl group; 
       (f7) a pyridyloxy group; 
       (f8) a pyridyloxy group having, on the ring, 1 to 4 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group; 
       (f10) a pyrimidyloxy group having, on the ring, 1 to 3 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group; 
       (f11) a pyrazyloxy group; 
       (f12) a pyrazyloxy group having, on the ring, 1 to 3 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group; 
       (f14) a pyrazolyloxy group having, on the ring, 1 to 3 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group, (g) a halo (C 1 -C 6 ) alkoxy group and (h) a formyl group; 
       (f15) a quinolyloxy group; 
       (f17) a quinoxalyloxy group; 
       (f19) a benzoxazolyloxy group; 
       (f21) a benzothiazolyloxy group; and 
       (f22) a benzothiazolyloxy group having, on the ring, 1 to 4 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group. 
     
     
         19 . The method according to  claim 12 , wherein
 A represents a nitrogen atom,   X 1  and X 2  may be the same or different, and are selected from the group consisting of   
       (a1) a hydrogen atom; 
       (a2) a halogen atom; and 
       (a4) a halo (C 1 -C 6 ) alkyl group,
 R 1  and R 2  each represent (b1) a hydrogen atom, 
 R 3  and R 4  may be the same or different, and are selected from the group consisting of 
 
       (c1) a hydrogen atom; and 
       (c3) a (C 1 -C 6 ) alkyl group,
 Y 1  represents 
 
       (d2) a halogen atom; or 
       (d3) a (C 1 -C 6 ) alkyl group,
 Y 2  and Y 4  each represent (e1) a hydrogen atom, and 
 Y 3  is selected from the group consisting of 
 
       (f1) a phenyl group; 
       (f2) a phenyl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (e) a halo (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group; 
       (f3) a phenoxy group; 
       (f4) a phenoxy group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1 -C 6 ) alkyl group, (f) a (C 1 -C 6 ) alkoxy group and (g) a halo (C 1 -C 6 ) alkoxy group; and 
       (f5) a pyridyl group.