Benzoylpyrazole compounds and herbicides containing them

Abstract

A benzoylpyrazole compound represented by the formula (I) or its salt: wherein R1 is alkyl or cycloalkyl, R2 is a hydrogen atom or alkyl, R3 is alkyl; cycloalkyl; haloalkyl; alkoxyalkyl; alkoxycarbonylalkyl; alkenyl; or arylalkyl which may be substituted by R8, R4 is alkyl; haloalkyl; alkoxy; halogen; nitro; cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl, R5 is a hydrogen atom; alkyl; alkenyl; alkynyl; halogen; cyano; cyanoalkyl; cyanoalkeny; haloalkyl; alkoxyalkyl; haloalkoxyalkyl; amino(thiocarbonyl)alkyl which may be substituted by at least one substituent selected from alkyl, cyano, is cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR7 and —C(O)SR7; thiocyanatoalkyl; alkoxy; alkenyloxy; alkynyloxy; haloalkoxy; alkoxyalkoxy; haloalkoxyalkoxy; alkoxyhaloalkoxy; haloalkoxyhaloalkoxy; alkoxyalkoxyalkyl; alkylthio; alkoxyalkylthio; haloalkoxyalkylthio; alkoxyhaloalkylthio; haloalkoxyhaloalkylthio; alkylthioalkylthio; haloalkylthioalkylthio; alkylthiohaloalkylthio; haloalkylthiohaloalkylthio; alkylthioalkoxy; alkylsulfonyl; alkylsulfonylalkyl; alkoxycarbonylalkyl; alkoxycarbonylalkoxy; heterocyclylalkyl; heterocyclyloxy; heterocyclylalkoxy; heterocyclylalkoxyalkyl; heterocyclyloxyalkyl; cycloalkyloxy; —OC(O)SR7; —OC(O)OR7; —C(O)OR7; —C(O)SR7; —C(S)OR7; —C(S)SR7; aminoalkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR7 and —C(O)SR7; or 4,5-dihydroisoxazol-3-yl which may be substituted by R9, R6 is haloalkyl; halogen; nitro; cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl, R7 is alkyl; haloalkyl; alkoxyalkyl; alkenyl; haloalkenyl; alkynyl; or arylalkyl which may be substituted by R10, and each of R8, R9 and R10 which are independent of one another, is halogen; alkyl; or alkoxy.

1 - 8 . (canceled) 
     
     
         9 . A benzoylpyrazole compound represented by the formula (II) or its salt: 
       
         
           
           
               
               
           
         
         wherein R 1  is alkyl or cycloalkyl; R 2  is a hydrogen atom or alkyl; R 4  is alkyl, haloalkyl, alkoxy, halogen, nitro, cyano, alkylthio, alkylsulfinyl, or alkylsulfonyl; R 5  is a hydrogen atom, alkyl, alkenyl, alkynyl, halogen, cyano, cyanoalkyl, cyanoalkenyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, amino(thiocarbonyl)alkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR 7  and —C(O)SR 7 , thiocyanatoalkyl, alkoxy, alkenyloxy, alkynyloxy, haloalkoxy, alkoxyalkoxy, haloalkoxyalkoxy, alkoxyhaloalkoxy, haloalkoxyhaloalkoxy, alkoxyalkoxyalkyl, alkylthio, alkoxyalkylthio, haloalkoxyalkylthio, alkoxyhaloalkylthio, haloalkoxyhaloalkylthio, alkylthioalkylthio, haloalkylthioalkylthio, alkylthiohaloalkylthio, haloalkylthiohaloalkylthio, alkylthioalkoxy, alkylsulfonyl, alkylsulfonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkoxy, heterocyclylalkyl, heterocyclyloxy, heterocyclylalkoxy, heterocyclylalkoxyalkyl, heterocyclyloxyalkyl, cycloalkyloxy, —OC(O)SR 7 , —OC(O)OR 7 , —C(O)OR 7 , —C(O)SR 7 , —C(S)OR 7 , —C(S)SR 7 , or aminoalkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR 7  and —C(O)SR 7 ; R 6  is haloalkyl, nitro, cyano, alkylthio, alkylsulfinyl, or alkylsulfonyl; R 7  is alkyl, haloalkyl, alkoxyalkyl, alkenyl, haloalkenyl, alkynyl, or arylalkyl which may be substituted by R 10 ; and each of R 8 , R 9  and R 10  which are independent of one another, is halogen, alkyl, or alkoxy. 
       
     
     
         10 . The benzoylpyrazole compound or its salt according to  claim 9 , wherein R 1  is methyl; R 2  is a hydrogen atom; R 4  is methyl; R 5  is 2-methoxyethoxy, and R 6  methylsulfonyl. 
     
     
         11 . The benzoylpyrazole compound or its salt according to  claim 9 , wherein R 1  is ethyl; R 2  is a hydrogen atom; R 4  is methyl; R 5  is 2-methoxyethoxy, and R 6  methylsulfonyl. 
     
     
         12 . A process for producing a benzoylpyrazole compound represented by the formula (II) or its salt: 
       
         
           
           
               
               
           
         
         wherein R 1  is alkyl or cycloalkyl; R 2  is a hydrogen atom or alkyl; R 4  is alkyl, haloalkyl, alkoxy, halogen, nitro, cyano, alkylthio, alkylsulfinyl, or alkylsulfonyl; R 5  is a hydrogen atom, alkyl, alkenyl, alkynyl, halogen, cyano, cyanoalkyl, cyanoalkenyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, amino(thiocarbonyl)alkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR 7  and —C(O)SR 7 , thiocyanatoalkyl, alkoxy, alkenyloxy, alkynyloxy, haloalkoxy, alkoxyalkoxy, haloalkoxyalkoxy, alkoxyhaloalkoxy, haloalkoxyhaloalkoxy, alkoxyalkoxyalkyl, alkylthio, alkoxyalkylthio, haloalkoxyalkylthio, alkoxyhaloalkylthio, haloalkoxyhaloalkylthio, alkylthioalkylthio, haloalkylthioalkylthio, alkylthiohaloalkylthio, haloalkylthiohaloalkylthio, alkylthioalkoxy, alkylsulfonyl, alkylsulfonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkoxy, heterocyclylalkyl, heterocyclyloxy, heterocyclylalkoxy, heterocyclylalkoxyalkyl, heterocyclyloxyalkyl, cycloalkyloxy, —OC(O)SR 7 , —OC(O)OR 7 , —C(O)OR 7 , —C(O)SR 7 , —C(S)OR 7 , —C(S)SR 7 , or aminoalkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR 7  and —C(O)SR 7 ; R 6  is haloalkyl, nitro, cyano, alkylthio, alkylsulfinyl, or alkylsulfonyl; R 7  is alkyl, haloalkyl, alkoxyalkyl, alkenyl, haloalkenyl, alkynyl, or arylalkyl which may be substituted by R 10 ; and each of R 8 , R 9  and R 10  which are independent of one another, is halogen, alkyl, or alkoxy, 
         which comprises rearrangement of a compound represented by the formula (VII): 
       
       
         
           
           
               
               
           
         
       
       wherein R 1 , R 2 , R 4 , R 5  and R 6  are as defined above. 
     
     
         13 . A process for producing a compound represented by the formula (VII): 
       
         
           
           
               
               
           
         
         wherein R 1  is alkyl or cycloalkyl; R 2  is a hydrogen atom or alkyl; R 4  is alkyl, haloalkyl, alkoxy, halogen, nitro, cyano, alkylthio, alkylsulfinyl, or alkylsulfonyl; R 5  is a hydrogen atom, alkyl, alkenyl, alkynyl, halogen, cyano, cyanoalkyl, cyanoalkenyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, amino(thiocarbonyl)alkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR 7  and —C(O)SR 7 , thiocyanatoalkyl, alkoxy, alkenyloxy, alkynyloxy, haloalkoxy, alkoxyalkoxy, haloalkoxyalkoxy, alkoxyhaloalkoxy, haloalkoxyhaloalkoxy, alkoxyalkoxyalkyl, alkylthio, alkoxyalkylthio, haloalkoxyalkylthio, alkoxyhaloalkylthio, haloalkoxyhaloalkylthio, alkylthioalkylthio, haloalkylthioalkylthio, alkylthiohaloalkylthio, haloalkylthiohaloalkylthio, alkylthioalkoxy, alkylsulfonyl, alkylsulfonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkoxy, heterocyclylalkyl, heterocyclyloxy, heterocyclylalkoxy, heterocyclylalkoxyalkyl, heterocyclyloxyalkyl, cycloalkyloxy, —OC(O)SR 7 , —OC(O)OR 7 , —C(O)OR 7 , —C(O)SR 7 , —C(S)OR 7 , —C(S)SR 7 , or aminoalkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR 7  and —C(O)SR 7 ; R 6  is haloalkyl, nitro, cyano, alkylthio, alkylsulfinyl, or alkylsulfonyl; R 7  is alkyl, haloalkyl, alkoxyalkyl, alkenyl, haloalkenyl, alkynyl, or arylalkyl which may be substituted by R 10 ; and each of R 8 , R 9  and R 10  which are independent of one another, is halogen, alkyl, or alkoxy, 
         which comprises reacting a compound represented by the formula (IX): 
       
       
         
           
           
               
               
           
         
       
       wherein R 4 , R 5  and R 6  are as defined above, with a compound represented by the formula (VIII) or its salt: 
       
         
           
           
               
               
           
         
       
       wherein R 1  and R 2  are as defined above. 
     
     
         14 . A process for producing a compound represented by the formula (IX): 
       
         
           
           
               
               
           
         
         wherein R 4  is alkyl, haloalkyl, alkoxy, halogen, nitro, cyano, alkylthio, alkylsulfinyl, or alkylsulfonyl; R 5  is a hydrogen atom, alkyl, alkenyl, alkynyl, halogen, cyano, cyanoalkyl, cyanoalkenyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, amino(thiocarbonyl)alkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR 7  and —C(O)SR 7 , thiocyanatoalkyl, alkoxy, alkenyloxy, alkynyloxy, haloalkoxy, alkoxyalkoxy, haloalkoxyalkoxy, alkoxyhaloalkoxy, haloalkoxyhaloalkoxy, alkoxyalkoxyalkyl, alkylthio, alkoxyalkylthio, haloalkoxyalkylthio, alkoxyhaloalkylthio, haloalkoxyhaloalkylthio, alkylthioalkylthio, haloalkylthioalkylthio, alkylthiohaloalkylthio, haloalkylthiohaloalkylthio, alkylthioalkoxy, alkylsulfonyl, alkylsulfonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkoxy, heterocyclylalkyl, heterocyclyloxy, heterocyclylalkoxy, heterocyclylalkoxyalkyl, heterocyclyloxyalkyl, cycloalkyloxy, —OC(O)SR 7 , —OC(O)OR 7 , —C(O)OR 7 , —C(O)SR 7 , —C(S)OR 7 , —C(S)SR 7 , or aminoalkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR 7  and —C(O)SR 7 ; R 6  is haloalkyl, nitro, cyano, alkylthio, alkylsulfinyl, or alkylsulfonyl; R 7  is alkyl, haloalkyl, alkoxyalkyl, alkenyl, haloalkenyl, alkynyl, or arylalkyl which may be substituted by R 10 ; and each of R 8 , R 9  and R 10  which are independent of one another, is halogen, alkyl, or alkoxy, 
         which comprises reacting a compound represented by the formula (X): 
       
       
         
           
           
               
               
           
         
       
       wherein R 4 , R 5  and R 6  are as defined above, with a halogenating agent. 
     
     
         15 . A compound represented by the formula (X) or its salt: 
       
         
           
           
               
               
           
         
         wherein R 4  is alkyl, haloalkyl, alkoxy, halogen, nitro, cyano, alkylthio, alkylsulfinyl, or alkylsulfonyl; R 5  is a hydrogen atom, alkyl, alkenyl, alkynyl, halogen, cyano, cyanoalkyl, cyanoalkenyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, amino(thiocarbonyl)alkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR 7  and —C(O)SR 7 , thiocyanatoalkyl, alkoxy, alkenyloxy, alkynyloxy, haloalkoxy, alkoxyalkoxy, haloalkoxyalkoxy, alkoxyhaloalkoxy, haloalkoxyhaloalkoxy, alkoxyalkoxyalkyl, alkylthio, alkoxyalkylthio, haloalkoxyalkylthio, alkoxyhaloalkylthio, haloalkoxyhaloalkylthio, alkylthioalkylthio, haloalkylthioalkylthio, alkylthiohaloalkylthio, haloalkylthiohaloalkylthio, alkylthioalkoxy, alkylsulfonyl, alkylsulfonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkoxy, heterocyclylalkyl, heterocyclyloxy, heterocyclylalkoxy, heterocyclylalkoxyalkyl, heterocyclyloxyalkyl, cycloalkyloxy, —OC(O)SR 7 , —OC(O)OR 7 , —C(O)OR 7 , —C(O)SR 7 , —C(S)OR 7 , —C(S)SR 7 , or aminoalkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR 7  and —C(O)SR 7 ; R 6  is haloalkyl, nitro, cyano, alkylthio, alkylsulfinyl, or alkylsulfonyl; R 7  is alkyl, haloalkyl, alkoxyalkyl, alkenyl, haloalkenyl, alkynyl, or arylalkyl which may be substituted by R 10 ; and each of R 8 , R 9  and R 10  which are independent of one another, is halogen, alkyl, or alkoxy, 
       
       wherein R 1  and R 2  are as defined above. 
     
     
         16 . The compound or its salt of  claim 15 , wherein R 4  is methyl, R 5  is 2-methoxyethoxy, and R 6  is methylsulfonyl.