Herbicidal 3-(pyrazolylphenyl)propanoic acids and derivatives

Abstract

Novel herbicidal compounds, compositions containing them, and methods for their preparation and use in controlling weeds are disclosed. The novel herbicidal compounds are 3-(pyrazolylphenyl)propanoic acids and derivatives having the formula: wherein X is H or halogen; Y is halogen, trihaloalkyl or cyano; Z and R are halogen; R 1 is carboxyl or agriculturally acceptable salt thereof, cyano, alkoxycarbonyl, alkylthiocarbonyl, alkoxyalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, or alkylsulfonylaminocarbonyl; and R 2 is hydrogen or lower alkyl.

What is claimed is:  
     
       1. A compound having the formula:                    
       wherein X is H or halogen; Y is halogen, trihaloalkyl or cyano; Z and R are halogen; R 1  is carboxyl or agriculturally acceptable salt thereof, cyano, alkoxycarbonyl, alkylthiocarbonyl, alkoxyalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, or alkylsulfonylaminocarbonyl; and R 2  is hydrogen or lower alkyl. 
     
     
       2. A compound of claim  1  wherein X is Cl or F; Y is Cl or Br; Z and R are Cl; R 1  is cyano, carboxyl or agriculturally acceptable salt thereof, alkoxycarbonyl, alkylthiocarbonyl, alkoxyalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, or alkylsulfonylaminocarbonyl; and R 2  is H or methyl. 
     
     
       3. A compound of claim  2  wherein Y is Cl; and R 2  is H. 
     
     
       4. A compound of claim  3  wherein R 1  is alkoxycarbonyl. 
     
     
       5. A compound of claim  4  wherein X is Cl. 
     
     
       6. A compound of claim  5  wherein R 1  is CO 2 CH 2 CH 3 . 
     
     
       7. A compound of claim  4  wherein X is F. 
     
     
       8. A compound of claim  7  wherein R 1  is CO 2 CH 2 CH 3 . 
     
     
       9. An herbicidal composition comprising an herbicidally effective amount of a compound of claim  1 , and an agriculturally acceptable carrier therefor. 
     
     
       10. A method of controlling undesired plant growth, comprising application to the locus where the undesired plants are growing or are expected to grow, an herbicidally effective amount of a composition of claim  9 . 
     
     
       11. An herbicidal composition comprising an herbicidally effective amount of a compound of claim  1  and an herbicidally effective amount of one or more herbicides selected from the group consisting of glyphosate, 2, 4-D, MCPA, MCPP, isoproturon, imazapyr, imazamethabenz, imazethapyr, imazaquin, acifluorfen, bifenox, fomasafen, ioxynil, bromoxynil, chlorimuron, chlorsulfuron, bensulfuron, pyrazosulfuron, thifensulfuron, triasulfuron, fenoxaprop, fluazifop, quizalofop, diclofop, bentazone, butachlor, dicamba, and fluroxypyr. 
     
     
       12. A method of controlling undesired plant growth, comprising application to the locus where the undesired plants are growing or are expected to grow, an herbicidally effective amount of a composition of claim  11 . 
     
     
       13. A process for preparing a compound of claim  1  which comprises the steps of: 
       a) preparing a mixture of an alkyl nitrite; a copper (II) halide selected from CuCl 2  and CuBr 2 ; and an activated olefin selected from the group consisting of CH 2 ═CHCO 2 -alkyl, CH 2 ═C(CH 3 )CO 2 -alkyl, CH 2 ═CHCN, and CH 2 ═C(CH 3 )CN in a suitable solvent; and  
       b) treating a compound having the formula:                    
       wherein X is H or halogen; Y is halogen, trihaloalkyl or cyano; and R are halogen with the mixture prepared in step a.