Herbicidal (oxaalkyl) phenyl-substituted heterocycles

Abstract

It has now been found that certain novel (oxaalkyl)phenyl-substituted heterocycles are useful as pre-emergent and post-emergent herbicides. These compounds are represented by formula I: ##STR1## where Q is a heterocycle and X, Y, R, R 1 , R 2 , and R 3 are substituents as described in the specification. Preferred are those compounds where Y and R are chloro; R 1 and R 2 are hydrogen or methyl; R 3 is hydrogen or alkylaminocarbonyl; X is fluorine; and Q is a 1-substituted-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl.

We claim: 
     
       1. A compound having the formula ##STR18## R is hydrogen, halogen, or alkyl; R 1  is hydrogen, cyano, or alkyl; R 2  is hydrogen, or alkyl;   R 3  is hydrogen, straight or branched chain alkyl carbonyl, alkoxycarbonyl, alkylaminocarbonyl, or cycloalkylaminocarbonyl;   X is hydrogen or halogen;   Y is halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, or nitro;   R 4  is hydrogen, amino, straight or branched chain alkyl, haloalkyl, cyanoalkyl, alkoxyalkyl, arylalkyl, alkoxycarbonylalkyl, arylalkyl, alkoxycarbonylalkyl, alkenyl, alkynyl, or a salt-forming ion; and   R 5  is halogen.   
     
     
       2. A compound of claim 1 where Q is 1-substituted-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl. 
     
     
       3. A compound of claim 1 where Q is 4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl. 
     
     
       4. A compound of claim 1 where Q is 4-halo-5-difluoromethoxy-1-methylpyrazol-3-yl. 
     
     
       5. A compound of claim 1 where Q is 3,4,5,6-tetrahydrophthalimid-1-yl. 
     
     
       6. A compound of claim 1 where Q is 1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazole-5-on-1-yl. 
     
     
       7. A compound of claim 1 where Q is 3-chloro-4,5,6,7-tetrahydroindazol-2-yl. 
     
     
       8. A compound of claim 1 where Q is 5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-A]pyridin-3(2H)-on-2-yl. 
     
     
       9. A compound of claim 1 where Q is 5,6,7,8-tetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazineimin-1-yl. 
     
     
       10. A compound of claim 1 where Q is 4-methyl-1,2,4-triazine-3,5-dion-3-yl. 
     
     
       11. A compound of claim 1 where Y and R are chloro; R 1  and R 2  are hydrogen or methyl; R 3  is hydrogen or alkylaminocarbonyl; and X is fluoro. 
     
     
       12. A compound of claim 11 where Q is 1-substituted-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl; and R 4  is methyl or amino. 
     
     
       13. A compound of claim 12 where R 3  is methylaminocarbonyl. 
     
     
       14. A herbicidal composition comprising a herbicidally effective amount of a compound of claim 1, and a herbicidally compatible carrier therefor. 
     
     
       15. A 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, (4-chloro-2-methylphenoxy)-acetic acid, (+/-)-2-(4-chloro-2-methylphenoxy)-propanoic acid, 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. 
     
     
       16. A composition of claim 15, and a herbicidally compatible carrier therefor. 
     
     
       17. A method of controlling undesired plant growth, comprising application to the locus where the undesired plants are growing or are expected to grow, a herbicidally effective amount of a composition of claim 14. 
     
     
       18. A method of controlling undesired plant growth, comprising application to the locus where the undesired plants are growing or are expected to grow, a herbicidally effective amount of a composition of claim 15.