Parasite- and hygienic pest-controlling agent

Abstract

There is provided a novel agent for controlling harmful arthropods or nematodes that are parasites and hygienic pests for animals. An ecto- or endo-parasiticide for mammals or the like comprising as active ingredient, one or more selected from substituted benzamide compounds of formula (1) or salts thereof: wherein A 1 is C—X 3 or nitrogen atom, etc., A 2 and A 3 are C—H, etc., A 4 is C—H or nitrogen atom, etc., G is G-2a, etc., W is oxygen atom or sulfur atom, X 1 is halogen atom, trifluoromethyl, etc., X 2 is hydrogen atom, halogen atom, trifluoromethyl, etc., X 3 is hydrogen atom, halogen atom, etc., Y 1 is hydrogen atom, halogen atom, methyl, etc., R 1 is trifluoromethyl, etc., R 2 is E-3a, etc., R 3 is hydrogen atom, etc., p is an integer of 0 to 2.

1 . A method for controlling parasites and hygienic pests comprising:
 administering to an animal a compound comprising a parasite- and hygienic pest-controlling composition comprising as an active ingredient a substituted benzamide compound of formula (1) or a salt thereof:   
       
         
           
           
               
               
           
         
         wherein A 3  is C—X 3  or nitrogen atom, 
         A 2 , A 3  and A 4  are independently of one another C—Y 2  or nitrogen atom, 
         G is a heterocyclic ring of following structural formulae G-1 to G-7: 
       
       
         
           
           
               
               
           
         
         W is oxygen atom or sulfur atom, 
         X 1  is hydrogen atom, halogen atom, C 1 -C 3 haloalkyl, halocyclopropyl, —OR 4 , —SF 5  or C 1 -C 3 haloalkylthio, 
         X 2  is hydrogen atom, halogen atom, cyano, nitro, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, —OR 4 , —S(O) p R 4  or —NH 2 , 
         X 3  is hydrogen atom, halogen atom, cyano, methyl, methoxy, difluoromethoxy, methylthio, —NH 2  or dimethylamino, or X 3  together with X 1  optionally forms 5-membered or 6-membered ring together with carbon atoms to which each of X 1  and X 3  is bonded by forming —CF 2 OCF 2 —, —OCF 2 O—, —CF 2 OCF 2 O— or —OCF 2 CF 2 O—, 
         Y 1  is hydrogen atom, halogen atom, cyano, nitro, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, (C 1 -C 2 )alkyl substituted with R 5 , C 3 -C 4 cycloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, —N(R 7 )R 6 , —C(S)NH 2 , C 2 -C 3 alkynyl, trimethylsilylethynyl, phenyl, phenyl substituted with (Z) n1  or D, 
         D is an aromatic heterocyclic ring of following structural formulae D-1 to D-3, D-7, D-11 and D-19 to D-23: 
       
       
         
           
           
               
               
           
         
         Z is halogen atom, cyano, nitro, methyl, trifluoromethyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, —NH 2  or dimethylamino, when n1 to n4 are an integer of 2 or more, each Z may be identical with or different from each other, 
         Y 2  is hydrogen atom, halogen atom or methyl, or when two Y 2 s are adjacent, the adjacent two Y 2 s may form 5-membered or 6-membered ring together with carbon atoms to which the two Y 2 s are bonded by forming ═NSN═ or —CH═CHCH═CH—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with Z, further when it is substituted with two or more Zs, each Z may be identical with or different from each other, 
         R 1  is C 1 -C 3 haloalkyl or halocyclopropyl, 
         R 1a  is hydrogen atom, halogen atom, C 1 -C 3 alkyl, C 1 -C 3 alkylthiomethyl, C 1 -C 3 haloalkylthiomethyl, C 1 -C 3 alkylsulfinylmethyl, C 1 -C 3 haloalkylsulfinylmethyl, C 1 -C 3 alkylsulfonylmethyl, C 1 -C 3 haloalkylsulfonylmethyl, —OH, C 1 -C 3 alkylthio or C 1 -C 3 alkylsulfonyl, 
         R 1b  is hydrogen atom or halogen atom, or R 1b  together with R 1a  optionally forms C 1 -C 4 alkylidene, phenylmethylidene, hydroxyimino or C 1 -C 3 alkoxyimino, 
         R 1c  is C 1 -C 3 alkyl, 
         R 2  is E or (C 1 -C 3 )alkyl substituted with E, 
         E is a heterocyclic ring of following structural formulae selected from the group consisting of E-1, E-2, E-3, E-4, E-5, E-7, E-8, E-9, E-10, E-11, E-12, and E-13: 
       
       
         
           
           
               
               
           
         
         R 3  is hydrogen atom, C 1 -C 4 alkyl, (C 1 -C 2 )alkyl substituted with R 11 , C 3 -C 4 cycloalkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, —C(O)R 12 , —C(O)OR 13 , —C(O)C(O)OR 13  or C 1 -C 3 haloalkylthio, R 4  is C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or C 1 -C 2 haloalkoxy (C 1 -C 2 )haloalkyl, R 5  is —OH, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio or C 1 -C 3 haloalkylthio, 
         R 6  is hydrogen atom, C 1 -C 4 alkyl, —CHO, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 3 -C 4 cycloalkylcarbonyl, C 1 -C 3 alkoxycarbonyl, C 1 -C 3 alkylthiocarbonyl, C 1 -C 3 alkoxythiocarbonyl, C 1 -C 3 alkyldithiocarbonyl, C 1 -C 3 alkylsulfonyl or C 1 -C 3 haloalkylsulfonyl, 
         R 7  is hydrogen atom or C 1 -C 3 alkyl, 
         R 8  is C 1 -C 3 alkyl, 
         R 9  is hydrogen atom, cyano or C 1 -C 2 haloalkylcarbonyl, 
         R 10  is hydrogen atom, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, hydroxy (C 1 -C 2 )alkyl, C 1 -C 3 alkoxy (C 1 -C 2 )alkyl, benzyl, C 3 -C 4 cycloalkyl, oxetan-3-yl, thietan-3-yl, C 3 -C 4 alkynyl, C 3 -C 4 alkenyl, phenyl or phenyl substituted with (Z) n1 , 
         R 11  is cyano, C 3 -C 4 cycloalkyl, —OR 14 , C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 haloalkylsulfinyl, C 1 -C 3 alkylsulfonyl, C 1 -C 3 haloalkylsulfonyl, C 1 -C 3 alkoxycarbonyl, —C(O)NH 2 , —C(S)NH 2i  phenyl or D-23, 
         R 12  is hydrogen atom, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 3 alkoxy (C 1 -C 2 )alkyl, C 1 -C 3 alkylthio (C 1 -C 2 )alkyl, C 1 -C 3 alkylsulfinyl (C 1 -C 2 )alkyl, C 1 -C 3 alkylsulfonyl (C 1 -C 2 )alkyl, C 3 -C 6 cycloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, phenyl, phenyl substituted with (Z) n1 , D-1, D-2 or D-23, 
         R 13  is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 3 alkoxy (C 1 -C 2 )alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl or phenyl, 
         R 14  is hydrogen atom, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl or C 1 -C 4 alkoxycarbonyl, 
         m is an integer of 0 to 5, 
         n1 is an integer of 1 to 5, 
         n2 is an integer of 0 to 3, 
         n3 is an integer of 0 to 4, 
         n4 is an integer of 0 to 2, 
         n5 is an integer of 0 or 1, 
         p is an integer of 0 to 2, and 
         q is an integer of 0 or 1. 
       
     
     
         2 . The method according to  claim 1 , wherein in the parasite- and hygienic pest-controlling composition,
 A 2  is C—H,   A 3  and A 4  are independently of one another C—Y 2  or nitrogen atom,   G is a heterocyclic ring of G-1, G-2, G-3, G-6 or G-7,   X 1  is halogen atom, trifluoromethyl, pentafluoroethyl, trifluoromethoxy, —SF 5  or trifluoromethylthio,   X 2  is hydrogen atom, halogen atom, cyano, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, difluoromethylthio or trifluoromethylthio,   X 3  is hydrogen atom, fluorine atom, chlorine atom, bromine atom, cyano or difluoromethoxy,   Y 1  is hydrogen atom, halogen atom, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxymethyl, cyclopropyl, difluoromethoxy, methylthio, —N(R 7 )R 6 , —C(S)NH 2  or ethynyl,   Y 2  is hydrogen atom, or when two Y 2 s are adjacent, the adjacent two Y 2 s may form 6-membered ring together with carbon atoms to which the two Y 2 s are bonded by forming —CH═CHCH═CH—,   R 1  is difluoromethyl, trifluoromethyl or chlorodifluoromethyl,   R 1a  is hydrogen atom, halogen atom, methyl, methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl,   R 1b  is hydrogen atom, or R 1b  together with R 1a  optionally forms C 2 -C 3 alkylidene,   R 1c  is methyl,   R 2  is E-3, E-4, E-5, —CH 2 -(E-1) or —CH 2 -(E-9),   R 3  is hydrogen atom, C 1 -C 3 alkyl, methyl substituted with R 11 , cyclopropyl, allyl, propargyl, —C(O)R 12  or —C(O)OR 13 ,   R 6  is hydrogen atom, methyl, C 1 -C 3 alkylcarbonyl or cyclopropylcarbonyl,   R 7  is hydrogen atom or methyl,   R 8  is methyl,   R 9  is hydrogen atom,   R 10  is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 3 alkoxy (C 1 -C 2 )alkyl, oxetan-3-yl or C 3 -C 4 alkynyl,   R 11  is cyano, methoxy, ethoxy or —C(S)NH 2 , R 12  is C 1 -C 4 alkyl, C 1 -C 3 alkoxy (C 1 -C 2 )alkyl, C 3 -C 4 cycloalkyl, C 2 -C 4 alkenyl or C 2 -C 4 alkynyl,   R 13  is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 3 alkoxy (C 1 -C 2 )alkyl, C 3 -C 4 alkenyl or C 3 -C 4 alkynyl,   m is an integer of 0 to 4, and   q is 1.   
     
     
         3 . The method according to  claim 2 , wherein in the parasite- and hygienic pest-controlling composition,
 A 3  is C—Y 2 ,   G is a heterocyclic ring of G-1 or G-2,   X 1  is halogen atom, trifluoromethyl, trifluoromethoxy or trifluoromethylthio,   X 2  is hydrogen atom, halogen atom, cyano or trifluoromethyl,   X 3  is hydrogen atom, fluorine atom, chlorine atom or difluoromethoxy,   Y 1  is hydrogen atom, halogen atom, nitro, methyl, ethyl, trifluoromethyl, methoxymethyl or —N(R 7 )R 6 ,   R 1  is trifluoromethyl or chlorodifluoromethyl,   R 1a  is hydrogen atom or halogen atom,   R 1b  is hydrogen atom,   R 2  is E-3,   R 3  is hydrogen atom, ethyl, cyanomethyl, methoxymethyl, propargyl, —C(O)R 12  or methoxycarbonyl, R 6  is hydrogen atom, methyl or acetyl,   R 10  is C 1 -C 3 alkyl or C 2 -C 3 haloalkyl,   R 12  is C 1 -C 4 alkyl or cyclopropyl, and   m is an integer of 0 or 1.   
     
     
         4 . The method according to  claim 3 , wherein in the parasite- and hygienic pest-controlling composition,
 A 3  and A 4  are C—H,   W is oxygen atom,   X 1  is chlorine atom, bromine atom, iodine atom or trifluoromethyl,   X 2  is hydrogen atom, halogen atom or trifluoromethyl,   X 3  is hydrogen atom, fluorine atom or chlorine atom,   Y 1  is halogen atom, nitro, methyl, ethyl or trifluoromethyl,   R 1  is trifluoromethyl,   R 1a  is hydrogen atom,   R 3  is hydrogen atom, and   m is 0.   
     
     
         5 . The method according to  claim 4 , wherein in the parasite- and hygienic pest-controlling composition,
 A 1  is C—X 3 ,   X 1  is chlorine atom, bromine atom or trifluoromethyl,   X 2  is chlorine atom, bromine atom or trifluoromethyl,   X 3  is hydrogen atom or fluorine atom,   Y 1  is chlorine atom, bromine atom or methyl, and   R 2  is E-3.   
     
     
         6 . The method according to  claim 1 , wherein in the parasite- and hygienic pest-controlling composition,
 G is a heterocyclic ring of G-1, and   R 2  is E-3.   
     
     
         7 . The method according to  claim 1 , wherein in the parasite- and hygienic pest-controlling composition,
 G is a heterocyclic ring of G-2,   R 1a  and R 1b  are hydrogen atom, and   R 2  is E-3.   
     
     
         8 . The method according to  claim 1 , wherein in the parasite- and hygienic pest-controlling composition,
 G is a heterocyclic ring of G-2,   R 1a  is halogen atom,   R 1b  are hydrogen atom, and   R 2  is E-3.   
     
     
         9 . The method according to  claim 1 , wherein administering the compound is an oral administration. 
     
     
         10 . The method according to  claim 1 , wherein administering the compound is a parenteral administration. 
     
     
         11 . The method according to  claim 10 , wherein the parenteral administration is a transdermal administration. 
     
     
         12 . The method according to  claim 9 , wherein in the parasite- and hygienic pest-controlling composition, the animals are mammals. 
     
     
         13 . The method according to  claim 12 , wherein in the parasite- and hygienic pest-controlling composition, the mammals are rabbit, guinea pig, hamster, Mongolian gerbil, mouse, rat, squirrel, monkey, dog, ferret, cat, yak, cattle, buffalo, goat, sheep, antelope, deer, reindeer, swine, pig, camel, alpaca, llama, donkey, horse or kangaroo. 
     
     
         14 . The method according to  claim 13 , wherein in the parasite- and hygienic pest-controlling composition, the mammals are dog or cat. 
     
     
         15 . The method according to  claim 1 , wherein in the parasite- and hygienic pest-controlling composition, the parasite is ecto-parasitic invertebrates for animals. 
     
     
         16 . The method according to  claim 15 , wherein in the parasite- and hygienic pest-controlling composition, the ecto-parasitic invertebrates for animals are flea, biting louse, louse, feather mite, itch mite, Cheyletidae, face mite, soft tick, hard tick, Dermanyssidae or Macronyssidae. 
     
     
         17 . The method according to  claim 16 , wherein in the parasite- and hygienic pest-controlling composition, the ecto-parasitic invertebrate for animals is flea, itch mite, Cheyletidae, face mite, soft tick or hard tick.