Herbicidal benzofuranyl derived uracils and production thereof

Abstract

It has now been found that certain novel benzofuranyl derived uracils have provided unexpected pre-emergent and post-emergent herbicidal efficacy. These compounds are represented by formula IPreferred are those of formula I where R is fluoroalkyl, carboxyalkyl, alkoxycarbonylalkyl, alkoxycarbonylhaloalkyl, alkenoxycarbonylalkyl, or mono- or dialkylaminocarbonylalkyl; X is halogen; Y is hydrogen or halogen; and, Z is methyl or amino. Novel intermediates to the compounds of formula I are also disclosed.

We claim:  
     
       1. A compound of the formula:                    
       wherein 
       R is fluoroalkyl, hydroxyalkyl, alkoxyalkyl, cyanoalkyl, carboxyalkyl, alkylcarbonyloxyalkyl, alkoxycarbonylalkyl, alkenoxycarbonylalkyl, alkoxycarbonylhaloalkyl, alkoxycarbonylalkoxyalkyl, alkoxycarbonylaminoalkyl, aminocarbonylalkyl, aminocarbonylalkoxyalkyl, mono or dialkylaminocarbonylalkyl, alkylcarbonylaminoalkyl, aminosulfinylalkyl, alkylaminosulfonylalkyl, alkylsulfonylaminoalkyl, 1,3-dioxolan-2-ylalkyl, or 1,3-oxazolin-2-ylalkyl;  
       X is halogen, cyano, nitro, or trihaloalkyl;  
       Y is hydrogen or halogen;  
       Z is hydrogen, alkyl, cyanoalkyl, alkenyl, alkynyl, amino, alkoxyalkyl, or alkoxycarbonylalkyl; with the proviso that when Z is methyl or amino R is not hydroxyalkyl, alkoxyalkyl, or alkylcarbonyloxyalkyl.  
     
     
       2. The compound according to claim  1  where R is fluoroalkyl, carboxyalkyl, alkoxycarbonylalkyl, alkoxycarbonylhaloalkyl, alkenoxycarbonylalkyl, or mono- or dialkylaminocarbonylalkyl where alkyl and alkoxy as part of the larger moiety are one to three carbon atoms and alkenoxy as part of the larger moiety is two to three carbon atoms; X is halogen; Y is hydrogen or halogen; and, Z is methyl or amino. 
     
     
       3. The compound according to claim  1  where R is fluoroalkyl, carboxyalkyl, alkoxycarbonylalkyl, or mono- or dialkylaminocarbonylalkyl where alkyl and alkoxy as part of the larger moiety are one to three carbon atoms; X is chlorine; Y is fluorine, and Z is methyl or amino. 
     
     
       4. The compound of claim  1 , which is selected from the group consisting of compounds 1-47 of Table 1. 
     
     
       5. A compound of the formula:                    
       wherein; 
       X is halogen, cyano, nitro, or trihaloalkyl;  
       Y is hydrogen or halogen;  
       Z is hydrogen, alkyl, cyanoalkyl, alkenyl, alkynyl, amino, alkoxyalkyl, or alkoxycarbonylalkyl.  
     
     
       6. The compound according to claim  5  where X is chlorine; Y is fluorine, and Z is hydrogen, methyl or amino. 
     
     
       7. An herbicidal composition comprising an herbicidally effective amount of a compound of claim  1 , and an herbicidally compatible carrier. 
     
     
       8. The herbicidal composition of claim  7 , further comprising one or more second compounds. 
     
     
       9. A method of controlling undesired plant growth, comprising applying an herbicidally effective amount of a composition of claim  7  to a locus where undesired plants are growing or are expected to grow. 
     
     
       10. An herbicidal composition comprising an herbicidally effective amount of a compound of claim  2 , and an herbicidally compatible carrier. 
     
     
       11. The herbicidal composition of claim  10 , further comprising one or more second compounds. 
     
     
       12. A method of controlling undesired plant growth, comprising applying an herbicidally effective amount of a composition of claim  10  to a locus where undesired plants are growing or are expected to grow. 
     
     
       13. An herbicidal composition comprising an herbicidally effective amount of a compound of claim  3 , and an herbicidally compatible carrier. 
     
     
       14. The herbicidal composition of claim  13 , further comprising on or more second compounds. 
     
     
       15. A method of controlling undesired plant growth, comprising applying an herbicidally effective amount of a composition of claim  13  to a locus where undesired plants are growing or are expected to grow. 
     
     
       16. An herbicidal composition comprising an herbicidally effective amount of a compound of claim  4 , and an herbicidally compatible carrier. 
     
     
       17. The herbicidal composition of claim  16 , further comprising on or more second compounds. 
     
     
       18. A method of controlling undesired plant growth, comprising applying an herbicidally effective amount of a composition of claim  16  to a locus where undesired plants are growing or are expected to grow.