Diarylimidazole compound and harmful organism control agent

Abstract

The present invention provides a compound represented by formula (I) or salt thereof (in the formula, A 1 and A 2 each independently represents a nitrogen atom or the like, B 1 , B 2 , B 3 and B 4 each independently represents a carbon atom or nitrogen atom, X 1 represents an unsubstituted or substituted C1-6 alkyl group or the like, n represents a number of X 1 and represents an integer of 0-4, R 1 represents a halogeno group or the like, R 2 represents an unsubstituted or substituted C1-6 alkyl group or the like, m represents a number of the oxide group bonding with the nitrogen atom which does not bond with R 2 on the imidazole ring, and represents 0 or 1, R 3 represents a hydrogen atom or the like, Ar represents an unsubstituted or substituted C6-10 aryl group.

1 . A compound represented by formula (II) or salt thereof 
       
         
           
           
               
               
           
         
         in formula (II) B 1 , B 2 , B 3  and B 4  each independently represents a carbon atom or a nitrogen atom, provided that when B 1  is a nitrogen atom, B 2  and B 4  represent a carbon atom and B 3  represents a carbon atom or a nitrogen atom, and when B 1  is a carbon atom, B 2  to B 4  represent a carbon atom or a nitrogen atom except that two or more of B 2  to B 4  simultaneously represent a nitrogen atom, 
         X 1  represents unsubstituted or substituted 3-6 membered heterocyclyl group, 
         n represents a chemically acceptable number of X 1  and represents an integer of 0 to 4, when n is 2 or more, X 1 s may be the same or different, and when n is 2 or more, two X 1 s may bond together to form a ring, 
         R 1  represents a halogeno group, hydroxy group, cyano group, substituted C1-6 alkyl group, unsubstituted or substituted C1-6 alkoxy group, unsubstituted or substituted C1-6 alkyl thio group, unsubstituted or substituted C1-6 alkyl sulfinyl group, unsubstituted or substituted C1-6 alkyl sulfonyl group, unsubstituted or substituted C1-6 alkyl sulfonyloxy group, C1-6 alkyl aminocarbonyl group, C1-6 alkyl sulfoximino group or a group represented by —S(═O)(═N—R a )—R b , in the formula, R a  represents a hydrogen atom, cyano group, C1-6 alkyl group or unsubstituted or substituted C1-6 alkyl carbonyl group, R b  represents a C1-6 alkyl group, 
         R 2  represents an unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C2-6 alkenyl group, unsubstituted or substituted C2-6 alkynyl group, unsubstituted or substituted C3-8 cycloalkyl group, hydroxy group, unsubstituted or substituted C1-6 alkoxy group, formyl group, unsubstituted or substituted C1-6 alkyl carbonyl group, unsubstituted or substituted C1-6 alkoxycarbonyl group, or unsubstituted or substituted C1-6 alkyl sulfonyl group, R 2  is a substituent bonding with any one of the two nitrogen atoms on the imidazole ring, 
         m represents a number of the oxide group bonding with the nitrogen atom which does not bond with R 2  on the imidazole ring, and represents 0 or 1, 
         R 3  represents a hydrogen atom, unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C6-10 aryl group, halogeno group, cyano group or nitro group, 
         Ar represents an unsubstituted or substituted C6-10 aryl group or unsubstituted or substituted 5-10 membered heteroaryl group. 
       
     
     
         2 . (canceled) 
     
     
         3 . A harmful organism control agent comprising as an active ingredient at least one selected from the group consisting of the compound and salt thereof defined in  claim 1 . 
     
     
         4 . An insecticide or acaricide comprising as an active ingredient at least one selected from the group consisting of the compound and salt thereof defined in  claim 1 . 
     
     
         5 . An external parasite control agent comprising as an active ingredient at least one selected from the group consisting of the compound and salt thereof defined in  claim 1 . 
     
     
         6 . An internal parasite control agent or expellent comprising as an active ingredient at least one selected from the group consisting of the compound and salt thereof defined in  claim 1 . 
     
     
         7 . A compound represented by formula (II) or salt thereof 
       
         
           
           
               
               
           
         
         in formula (II), B 1 , B 2 , B 3  and B 4  each independently represents a carbon atom or a nitrogen atom, provided that when B 1  is a nitrogen atom, B 2  and B 4  represent a carbon atom and B 3  represents a carbon atom or a nitrogen atom, and when B 1  is a carbon atom, B 2  to B 4  represent a carbon atom or a nitrogen atom except that two or more of B 2  to B 4  simultaneously represent a nitrogen atom, 
         X 1  represents an unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C2-6 alkenyl group, unsubstituted or substituted C2-6 alkynyl group, hydroxy group, unsubstituted or substituted C1-6 alkoxy group, formyl group, unsubstituted or substituted C1-6 alkyl carbonyl group, unsubstituted or substituted C1-6 alkoxycarbonyl group, unsubstituted or substituted C1-6 alkyl aminocarbonyl group, mercapto group, unsubstituted or substituted C1-6 alkyl thio group, unsubstituted or substituted C1-6 alkyl sulfinyl group, unsubstituted or substituted C1-6 alkyl sulfonyl group, unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted amino group, halogeno group, cyano group, or nitro group, 
         n represents a chemically acceptable number of X 1  and represents an integer of 0 to 4, when n is 2 or more, X 1 s may be the same or different, and when n is 2 or more, two X 1 s may bond together to form a ring, 
         R 1  represents a halogeno group, hydroxy group, cyano group, substituted C1-6 alkyl group, unsubstituted or substituted C1-6 alkoxy group, unsubstituted or substituted C1-6 alkyl thio group, unsubstituted or substituted C1-6 alkyl sulfinyl group, unsubstituted or substituted C1-6 alkyl sulfonyl group, unsubstituted or substituted C1-6 alkyl sulfonyloxy group, C1-6 alkyl aminocarbonyl group, C1-6 alkyl sulfoximino group or a group represented by —S(═O)(═N—R a )—R b , in the formula, R a  represents a hydrogen atom, cyano group, C1-6 alkyl group or unsubstituted or substituted C1-6 alkyl carbonyl group, R b  represents a C1-6 alkyl group, 
         R 2  represents an unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C2-6 alkenyl group, unsubstituted or substituted C2-6 alkynyl group, unsubstituted or substituted C3-8 cycloalkyl group, hydroxy group, unsubstituted or substituted C1-6 alkoxy group, formyl group, unsubstituted or substituted C1-6 alkyl carbonyl group, unsubstituted or substituted C1-6 alkoxycarbonyl group, or unsubstituted or substituted C1-6 alkyl sulfonyl group, R 2  is a substituent bonding with any one of the two nitrogen atoms on the imidazole ring, 
         m represents a number of the oxide group bonding with the nitrogen atom which does not bond with R 2  on the imidazole ring, and represents 0 or 1, 
         R 3  represents a hydrogen atom, unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C6-10 aryl group, halogeno group, cyano group or nitro group, 
         Ar represents an unsubstituted or substituted 5-10 membered heteroaryl group. 
       
     
     
         8 . A compound represented by formula (II) or salt thereof 
       
         
           
           
               
               
           
         
         in formula (II), B 1 , B 2 , B 3  and B 4  each independently represents a carbon atom or a nitrogen atom, provided that when B 1  is a nitrogen atom, B 2  and B 4  represent a carbon atom and B 3  represents a carbon atom or a nitrogen atom, and when B 1  is a carbon atom, B 2  and B 4  represent a carbon atom and B 3  represents a nitrogen atom, or when B 1  is a carbon atom, B 2  and B 3  represent a carbon atom and B 4  represents a nitrogen atom, 
         X 1  represents an unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C2-6 alkenyl group, unsubstituted or substituted C2-6 alkynyl group, hydroxy group, unsubstituted or substituted C1-6 alkoxy group, formyl group, unsubstituted or substituted C1-6 alkyl carbonyl group, unsubstituted or substituted C1-6 alkoxycarbonyl group, unsubstituted or substituted C1-6 alkyl aminocarbonyl group, mercapto group, unsubstituted or substituted C1-6 alkyl thio group, unsubstituted or substituted C1-6 alkyl sulfinyl group, unsubstituted or substituted C1-6 alkyl sulfonyl group, unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted amino group, halogeno group, cyano group, or nitro group, 
         n represents a chemically acceptable number of X 1  and represents an integer of 0 to 4, when n is 2 or more, X 1 s may be the same or different, and when n is 2 or more, two X 1 s may bond together to form a ring, 
         R 1  represents a halogeno group, hydroxy group, cyano group, substituted C1-6 alkyl group, unsubstituted or substituted C1-6 alkoxy group, unsubstituted or substituted C1-6 alkyl thio group, unsubstituted or substituted C1-6 alkyl sulfinyl group, unsubstituted or substituted C1-6 alkyl sulfonyl group, unsubstituted or substituted C1-6 alkyl sulfonyloxy group, C1-6 alkyl aminocarbonyl group, C1-6 alkyl sulfoximino group or a group represented by —S(═O)(═N—R a )—R b , in the formula, R a  represents a hydrogen atom, cyano group, C1-6 alkyl group or unsubstituted or substituted C1-6 alkyl carbonyl group, R b  represents a C1-6 alkyl group, 
         R 2  represents an unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C2-6 alkenyl group, unsubstituted or substituted C2-6 alkynyl group, unsubstituted or substituted C3-8 cycloalkyl group, hydroxy group, unsubstituted or substituted C1-6 alkoxy group, formyl group, unsubstituted or substituted C1-6 alkyl carbonyl group, unsubstituted or substituted C1-6 alkoxycarbonyl group, or unsubstituted or substituted C1-6 alkyl sulfonyl group, R 2  is a substituent bonding with any one of the two nitrogen atoms on the imidazole ring, 
         m represents a number of the oxide group bonding with the nitrogen atom which does not bond with R 2  on the imidazole ring, and represents 0 or 1, 
         R 3  represents a hydrogen atom, unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C6-10 aryl group, halogeno group, cyano group or nitro group, 
         Ar represents an unsubstituted or substituted C6-10 aryl group.