Tetrazoyloxime derivative and plant disease control agent

Abstract

According to the present invention, a tetrazoyloxime derivative and a salt thereof, which are excellent in a control effect against plant disease injury, and a plant disease controlling agent containing the same as an active ingredient are provided. The tetrazoyloxime derivative has a structure represented by formula (1) shown below: wherein X represents a halogen atom, etc., n1 represents an integer of 0 to 5, A represents a group represented by formula (2) or (3), and Het represents a group represented by formula (4) or (5): wherein Y represents a C 1-8 alkyl group, R represents a halogen atom, etc., n2 represents an integer of 0 to 3, R 11 represents a halogen atom, etc., and Z or Z 11 represents a group represented by formula: Q 1 C(═O)NH—, etc. (in which Q 1 represents a C 2-8 haloalkenyl group, etc.) (depends on the kind of R or R 11 ).

1 . A tetrazoyloxime derivative represented by formula (1): 
     
       
         
         
             
             
         
       
     
     wherein X represents a halogen atom, a C 1-8  alkyl group, a C 1-8  alkoxy group, a cyano group, a C 1-8  alkylsulfonyl group, a nitro group, a C 1-8  haloalkyl group, or an unsubstituted or substituted aryl group;
 n1 represents any one of integers of 0 to 5, and 
 when n1 is 2 or more, X(s) may be the same or different with each other; 
 A represents a tetrazoyl group represented by formula (2): 
 
     
       
         
         
             
             
         
       
     
     (in which Y represents a C 1-8  alkyl group), or a tetrazoyl group represented by formula (3): 
     
       
         
         
             
             
         
       
     
     (in which Y is the same as defined above); and
 Het represents a pyridyl group represented by formula (4): 
 
     
       
         
         
             
             
         
       
     
     (in which R represents a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted C 1-8  alkyl group, an unsubstituted or substituted C 2-8  alkenyl group, an unsubstituted or substituted C 2-8  alkynyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, OR 1 , S(O) m R 1 , COR 1 , or CO 2 R 1 , R 1  represents an unsubstituted or substituted amino group, an unsubstituted or substituted C 1-8  alkyl group, an unsubstituted or substituted C 3-8  cycloalkyl group, an unsubstituted or substituted C 2-8  alkenyl group, an unsubstituted or substituted C 2-8  alkynyl group, or an unsubstituted or substituted aryl group,
 m represents any one of integers of 0 to 2, 
 n2 represents any one of integers of 0 to 3, and 
 when n2 is 2 or more, plural R(s) may be the same or different from each other, 
 when n2 is 0, Z represents a group represented by formula: Q 1 C(═O)NH— (in which Q 1  represents a C 1-8  haloalkyl group, a C 2-8  haloalkenyl group, a C 2-8  alkynyl group, a C 2-8  haloalkynyl group, a C 1-8  haloalkoxy group, a C 2-8  alkenyloxy group, a C 2-8  haloalkenyloxy group, a C 2-8  alkynyloxy group, a C 2-8  haloalkynyloxy group, a C 1-8  alkoxy group substituted with an alkoxycarbonylamino group, a C 1-8  alkoxy group substituted with a C 3-8  cycloalkyl group, a C 1-8  branched alkoxy group substituted with an unsubstituted aryl group, a C 1-8  alkoxy group substituted with substituted aryl, a C 1-8  alkoxy group substituted with an unsubstituted or substituted heterocyclic group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted C 1-8  alkoxy group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted aryloxy group, an C 1-8  alkoxy group substituted with an unsubstituted or substituted aralkyloxy group, a C 2-8  alkynyloxy group substituted with an unsubstituted or substituted aryl group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted C 1-8  alkylthio group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted arylthio group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted C 1-8  alkylsulfinyl group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted arylsulfinyl group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted C 1-8  alkylsulfonyl group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted arylsulfonyl group, a C 1-8  alkoxy group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted alkyl group), a C 1-8  alkoxy group which is substituted with an amino group substituted with an (unsubstituted or substituted aralkyl group), an unsubstituted or substituted aryloxy group, a C 1-8  alkyl group substituted with a carboxyl group, a C 1-8  alkyl group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted aralkyl group), a C 1-8  alkyl group substituted with an amino group which is substituted with an (unsubstituted or substituted alkyl group), a C 1-8  alkyl group substituted with an unsubstituted or substituted aryloxy group, a C 1-8  alkyl group substituted with an acyl group, or a C 1-8  alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group), 
 when n2 is 1 and R is a halogen atom, Z represents a hydrogen atom, an amino group, or a group represented by formula: Q 2 C(═O)NH— (in which Q 2  represents a hydrogen atom, a C 1-8  haloalkyl group, a C 2-8  alkenyl group, a C 2-8  haloalkenyl group, a C 2-8  alkynyl group, a C 2-8  haloalkynyl group, a C 1-8  alkoxy group, a C 1-8  haloalkoxy group, a C 2-8  alkenyloxy group, a C 2-8  haloalkenyloxy group, a C 2-8  alkynyloxy group, a C 2-8  haloalkynyloxy group, a C 3-8  cycloalkyl group, a C 3-8  cycloalkyloxy group, a C 1-8  alkylamino group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted amino group, a C 1-8  alkoxy group substituted with a C 3-8  cycloalkyl group, an unsubstituted or substituted aralkyloxy group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted heterocyclic group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted C 1-8  alkoxy group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted aryloxy group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted aralkyloxy group, a C 2-8  alkynyloxy group substituted with an unsubstituted or substituted aryl group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted C 1-8  alkylthio group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted arylthio group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted C 1-8  alkylsulfinyl group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted arylsulfinyl group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted C 1-8  alkylsulfonyl group, C 1-8  alkoxy group substituted with an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted aryloxy group, a C 1-8  alkyl group substituted with a carboxyl group, a C 1-8  alkyl group substituted with an unsubstituted or substituted amino group, a C 1-8  alkyl group substituted with an unsubstituted or substituted aryloxy group, a C 1-8  alkyl group substituted with an unsubstituted or substituted C 1-8  alkylthio group, a C 1-8  alkyl group substituted with an unsubstituted or substituted alkoxy group, a C 1-8  alkyl group substituted with an acyl group, or a C 1-8  alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group), 
 when n2 is 1 or more and at least one R is a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted C 1-8  alkyl group, an unsubstituted or substituted C 2-8  alkenyl group, an unsubstituted or substituted C 2-8  alkynyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, OR 1 , S(O) m R 1 , COR 1 , or CO 2 R 1 , or when n2 is 2 or more and at least two R(s) are halogen atoms, Z represents a hydrogen atom, an amino group, or a group represented by formula: Q 3 C(═O)NH— (in which Q 3  represents a hydrogen atom, a C 1-8  alkyl group, a C 1-8  haloalkyl group, a C 2-8  alkenyl group, a C 2-8  haloalkenyl group, a C 2-8  alkynyl group, a C 2-8  haloalkynyl group, a C 1-8  alkoxy group, a C 1-8  haloalkoxy group, a C 2-8  alkenyloxy group, a C 2-8  haloalkenyloxy group, a C 2-8  alkynyloxy group, a C 2-8  haloalkynyloxy group, a C 3-8  cycloalkyl group, a C 3-8  cycloalkyloxy group, a C 1-8  alkylamino group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted amino group, a C 1-8  alkoxy group substituted with a C 3-8  cycloalkyl group, an unsubstituted or substituted aralkyloxy group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted heterocyclic group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted C 1-8  alkoxy group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted aryloxy group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted aralkyloxy group, a C 2-8  alkynyloxy group substituted with an unsubstituted or substituted aryl group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted C 1-8  alkylthio group, a C 1-8  alkoxy group substituted with a substituted or unsubstituted arylthio group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted C 1-8  alkylsulfinyl group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted arylsulfinyl group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted C 1-8  alkylsulfonyl group, a C 1-8  alkoxy group substituted with an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted aryloxy group, a C 1-8  alkyl group substituted with a carboxyl group, a C 1-8  alkyl group substituted with an unsubstituted or substituted amino group, a C 1-8  alkyl group substituted with an unsubstituted or substituted aryloxy group, a C 1-8  alkyl group substituted with an unsubstituted or substituted C 1-8  alkylthio group, a C 1-8  alkyl group substituted with an unsubstituted or substituted alkoxy group, an alkyl group substituted with an acyl group, or a C 1-8  alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group), or a thiazoyl group represented by formula (5): 
 
     
       
         
         
             
             
         
       
     
     (in which R 11  represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted C 1-8  alkyl group, an unsubstituted or substituted C 2-8  alkenyl group, an unsubstituted or substituted C 2-4  alkynyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, OR 1 , S(O) m R 1 , COR 1 , or CO 2 R 1 ,
 R 1  is the same as defined above, 
 when R 11  is a hydrogen atom, Z 11  represents a group represented by formula: Q 1 C(═O)NH— (in which Q 1  is the same as defined above), 
 when R 11  is a halogen atom, Z 11  represents a hydrogen atom, an amino group, or a group represented by formula: Q 2 C(═O)NH— (in which Q 2  is the same as defined above), and when R 11  is a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted C 1-8  alkyl group, an unsubstituted or substituted C 2-8  alkenyl group, an unsubstituted or substituted C 2-8  alkynyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, OR 1 , S(O) m R 1 , COR 1 , or CO 2 R 1 , Z 11  represents a hydrogen atom, an amino group, or a group represented by formula: Q 3 C(═O)NH— (in which Q 3  is the same as defined above), and a salt thereof. 
 
   
   
       2 . The tetrazoyloxime derivative according to  claim 1 , wherein n1 is 0 or X is halogen atom, and a salt thereof. 
   
   
       3 . The tetrazoyloxime derivative according to  claim 1 , wherein Y is a methyl group, and a salt thereof. 
   
   
       4 . A plant disease controlling agent comprising the tetrazoyloxime derivative according to  claim 1  or a salt thereof as an active ingredient. 
   
   
       5 . The tetrazoyloxime derivative according to  claim 2 , wherein Y is a methyl group, and a salt thereof. 
   
   
       6 . A plant disease controlling agent comprising the tetrazoyloxime derivative according to  claim 2  or a salt thereof as an active ingredient. 
   
   
       7 . A plant disease controlling agent comprising the tetrazoyloxime derivative according to  claim 3  or a salt thereof as an active ingredient. 
   
   
       8 . A plant disease controlling agent comprising the tetrazoyloxime derivative according to  claim 5  or a salt thereof as an active ingredient.