Isoxazoline-substituted benzamide compound and pesticide

Abstract

A substituted alkenylbenzene compound of formula (4): wherein X 1 is selected from the group consisting of a halogen atom, —SF 5 , C 1 -C 6 haloalkyl, hydroxy C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy C 1 -C 6 haloalkyl, C 3 -C 8 halocycloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 3 haloalkoxy C 1 -C 3 haloalkoxy, C 1 -C 6 haloalkylthio, C 1 -C 6 haloalkylsulfinyl and C 1 -C 6 haloalkylsulfonyl; X 3 is selected from the group consisting of a hydrogen atom, halogen atom, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy and C 1 -C 6 alkylthio; X 4 is selected from the group consisting of a hydrogen atom, halogen atom, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy; R 3 is —C(R 3a )(R 3b )R 3c , where R 3a and R 3b independently of each other are a halogen atom, or R 3a and R 3b together form 3- to 6-membered ring together with the carbon atom bonding them by forming a C 2 -C 5 haloalkylene chain, and R 3c is selected from the group consisting of a hydrogen atom, halogen atom, C 1 -C 5 alkyl, C 1 -C 5 haloalkyl, C 1 -C 4 haloalkoxy and C 1 -C 4 haloalkylthio, with a proviso that in case where X 1 is a fluorine atom, chlorine atom or trifluoromethyl, and both X 2 and X 3 are a hydrogen atom, in case where both X 1 and X 2 are fluorine atom and X 3 is a hydrogen atom, and in case where both X 1 and X 2 are trifluoromethyl and X 3 is a hydrogen atom, R 3c is a hydrogen atom, chlorine atom, bromine atom, iodine atom, C 1 -C 5 alkyl, C 1 -C 5 haloalkyl, C 1 -C 4 haloalkoxy or C 1 -C 4 haloalkylthio.

1 . (canceled) 
     
     
         2 . (canceled) 
     
     
         3 . A method for killing fleas, the method comprising contacting the fleas with an effective amount of a compound of the formula: 
       
         
           
           
               
               
           
         
         or a salt thereof, 
         wherein 
         (X) m  is 3,5-Cl 2  or 3,5-Br 2 ; 
         R 3  is CF 3  or CF 2 Cl; 
         (Y) n  is 2-CH 3  or 2-I; and 
         R 1  is CH 2 C(O)NHCH 3 , CH 2 C(O)N(CH 3 ) 2 , CH 2 C(O)NHEt, CH 2 C(O)NHPr-i, CH 2 C(O)NHCH 2 CH 2 C 1 , CH 2 C(O)NHCH 2 CF 3 , CH 2 C(O)NHCH 2 CH═CH 2 , CH 2 C(O)N(CH 3 )CH 2 CH═CH 2 , CH 2 C(O)NHCH 2 C≡CH, CH(CH 3 )C(O)NHCH 2 CH 2 C 1 , (E-9b)CH 2 CF 3 , or CH(CH 3 )C(O)NHCH 2 CF 3 ,
 wherein Et is ethyl, Pr-i is isopropyl, and (E-9b)CH 2 CF 3  is a saturated heterocyclic ring of the following formula: 
 
       
       
         
           
           
               
               
           
         
       
     
     
         4 . A method according to  claim 3 , wherein contacting the fleas with the compound comprises orally administering the compound to a mammal. 
     
     
         5 . A method according to  claim 4 , wherein the mammal is livestock. 
     
     
         6 . A method according to  claim 4 , wherein the mammal is a domestic animal. 
     
     
         7 . A method according to  claim 4 , wherein the mammal is a pet. 
     
     
         8 . A method according to  claim 4 , wherein the mammal is a dog. 
     
     
         9 . A method according to  claim 4 , wherein the mammal is a cat. 
     
     
         10 . A method for killing fleas, the method comprising contacting the fleas with an effective amount of a compound of the formula: 
       
         
           
           
               
               
           
         
         or a salt thereof, 
         wherein 
         (X) m  is 3,5-Cl 2 , 3,5-Br 2 , 3,5-(CF 3 ) 2 , 3,4-Cl 2 , or 3,5-Cl 2 -4-CH 3 ; 
         R 3  is CF 3  or CF 2 Cl; 
         (Y) n  is 2-CH 3 , 2-Cl, or 2-I; 
         R 1  is CH(CH 3 )CH 2 OCH 3 , c-Bu, CH 2 CF 3 , CH 2 CH 2 OCH 3 , CH 2 (E-10a), CH 2 CH 2 SEt, CH 2 CH(CH 3 )S(O)CH 3 , CH 2 CH(CH 3 )SO 2 CH 3 , CH 2 C(O)CH 3 , CH(CH 3 )C(O)OCH 3 , CH 2 C(O)NHEt, CH 2 C(O)NHPr-i, CH 2 C(O)NHCH 2 CH 2 Cl, CH 2 C(O)NHCH 2 CF 3 , CH 2 C(O)NHCH 2 CH═CH 2 , CH 2 C(O)N(CH 3 )CH 2 CH═CH 2 , CH 2 C(O)NHCH 2 C≡CH, CH(CH 3 )C(O)NHCH 2 CH 2 Cl, CH 2 CH═CH 2 , CH 2 (D-17a)CH 3 , CH 2 (D-17b)Cl, CH 2 (D-22a), CH 2 (D-47a), CH(CH 3 )(D-47a), CH 2 (D-48e)Cl, CH 2 (D-50a), CH 2 (D-51a), N(CH 3 )Ph, D-51a, CH 2 CH 2 OEt, CH 2 CH 2 CF 3 , CH(CF 3 )OCH 3 , (E-9b)CH 2 CF 3 , CH(CH 3 )C(O)NHCH 2 CF 3 , CH(CH 3 )(D-21a), CH(CF 3 )(D-38a), C(O)NHCH 2 CF 3 , C(S)NHCH 2 CF 3 , (D-15a)CH 3 , (D-50c)Cl, CH 2 OEt, CH 2 OCH 2 CH 2 Cl, CH 2 OCH 2 CHF 2 , CH 2 OCH 2 CF 3 , E-4a, C(O)NHCH 2 CH═CH 2 , or Ph-3-F,
 wherein c-Bu is cyclobutyl, Et is ethyl, Pr-i is isopropyl, and Ph is phenyl, 
 wherein E-4a, (E-9b)CH 2 CF 3 , and E-10a are saturated heterocyclic rings of the following formulae: 
 
       
       
         
           
           
               
               
           
         
         
           wherein (D-15a)CH 3 , (D-17a)CH 3 , (D-17b)Cl, (D-21a), (D-22a), (D-38a), (D-47a), (D-48e)Cl, (D-50a), (D-50c)Cl, and (D-51a) are aromatic heterocyclic rings of the following formulae: 
         
       
       
         
           
           
               
               
           
         
       
     
     
         11 . A method according to  claim 10 , wherein contacting the fleas with the compound comprises orally administering the compound to a mammal. 
     
     
         12 . A method according to  claim 11 , wherein the mammal is livestock. 
     
     
         13 . A method according to  claim 11 , wherein the mammal is a domestic animal. 
     
     
         14 . A method according to  claim 11 , wherein the mammal is a pet. 
     
     
         15 . A method according to  claim 11 , wherein the mammal is a dog. 
     
     
         16 . A method according to  claim 11 , wherein the mammal is a cat.