Hydrazine oxoacetamide derivative and insecticide

Abstract

The present invention relates to a hydrazine oxoacetamide derivative or its salt which exhibits an excellent insecticidal effect even at a low concentration. The hydrazine oxoacetamide derivative has the following Formula (I): wherein R 1 represents a chlorine atom or a bromine atom, Y represents an oxygen atom or a methylene group, and when Y is an oxygen atom, p is 2 and when Y is a methylene group, p is 0, R 2 represents a trifluoromethyl group, R 3 represents a hydrogen atom or a methyl group, R 4 represents a hydrogen atom or a methyl group, and R 5 represents a methyl group, an ethyl group, an n-propyl group, a cyclopropyl group, an allyl group or a propargyl group.

What is claimed is:  
     
         1 . A hydrazine oxoacetamide derivative having the following formula or a salt thereof:  
       
         
           
           
               
               
           
         
       
       wherein 
 R 1  represents a chlorine atom or a bromine atom,  
 Y represents an oxygen atom or a methylene group, and when y is an oxygen atom, p is 2 and when y is a methylene group, p is 0,  
 R 2  represents a trifluoromethyl group,  
 R 3  represents a hydrogen atom or a methyl group,  
 R 4  represents a hydrogen atom or a methyl group, and  
 R 5  represents a methyl group, an ethyl group, an n-propyl group, a cyclopropyl group, an allyl group or a propargyl group.  
 
     
     
         2 . The hydrazine oxoacetamide derivative or its salt of  claim 1  wherein R 1  represents a chlorine atom.  
     
     
         3 . The hydrazine oxoacetamide derivative or its salt of  claim 1  wherein R 5  represents an ethyl group.  
     
     
         4 . An insecticide containing the hydrazine oxoacetamide derivative or its salt of  claim 1  as an active ingredient.  
     
     
         5 . The insecticide of  claim 4 , which is effective against  Spodoptera litura, Plutella xylostella, Mamestra brassicae, Spodptera exigua  or Adoxophyes sp.  
     
     
         6 . The insecticide of  claim 4 , which contains 0.002 to 80% by weight of the hydrazine oxoacetamide derivative or its salt.  
     
     
         7 . The insecticide of  claim 4 , which contains 0.01 to 70% by weight of the hydrazine oxoacetamide derivative or its salt.  
     
     
         8 . A process for producing a hydrazine oxoacetamide derivative of  claim 1 , which comprises reacting a compound having the following Formula (VIII):  
       
         
           
           
               
               
           
         
       
       wherein 
 R 1  represents a chlorine atom or a bromine atom,  
 R 2  represents a trifluoromethyl group,  
 R 3  represents a hydrogen atom or a methyl group, and  
 Y represents an oxygen atom or a methylene group, and when Y is an oxygen atom, p is 2 and when Y is a methylene group, p is 0,  
 with a compound having the following Formula (IX):  
                     
  wherein 
 R 4  represents a hydrogen atom or a methyl group, and  
 R 5  represents a methyl group, an ethyl group, an n-propyl group, a cyclopropyl group, an allyl group or a propargyl group.  
 
 
     
     
         9 . A process for producing a hydrazine oxoacetamide derivative of  claim 1 , which comprises reacting a compound having the following Formula (X):  
       
         
           
           
               
               
           
         
       
       wherein 
 R 1  represents a chlorine atom or a bromine atom,  
 R 2  represents a trifluoromethyl group,  
 R 3  represents a hydrogen atom or a methyl group, and  
 Y represents an oxygen atom or a methylene group, and when Y is an oxygen atom, p is 2 and when Y is a methylene group, p is 0,  
 with a compound having the following Formula (XI):  
                     
  wherein 
 R 4  represents a hydrogen atom or a methyl group,  
 R 5  represents a methyl group, an ethyl group, an n-propyl group, a cyclopropyl group, an allyl group or a propargyl group, and  
 X represents a halogen atom.  
 
 
     
     
         10 . A process for producing a hydrazine oxoacetamide derivative of  claim 1 , which comprises reacting a compound having the following Formula (I):  
       
         
           
           
               
               
           
         
       
       wherein 
 R 1  represents a chlorine atom or a bromine atom,  
 Y represents an oxygen atom or a methylene group, and when Y is an oxygen atom, p is 2 and when Y is a methylene group, p is 0,  
 R 2  represents a trifluoromethyl group,  
 R 3  and R 4  each represent a hydrogen atom or a methyl group, with the proviso that one or both of R 3  and R 4  are hydrogen atoms, and  
 R 5  represents a methyl group, an ethyl group, an n-propyl group, a cyclopropyl group, an allyl group or a propargyl group.  
 with a compound having the following Formula (XII): 
 X—R 7   (XII) 
  wherein R 7  represents a methyl group, or  
 with a compound having the following Formula (XIII): 
 (R 8 O) 2 SO 2   (XIII) 
  wherein R 8  represents a methyl group.