Herbicidal benzyloxyphenyl-substituted heterocycles

Abstract

It has now been found that certain novel benzyloxyphenyl-substituted heterocycles are useful as pre-emergent and post-emergent herbicides. These compounds are represented by formula I: ##STR1## where Q is 1-substituted-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3 -yl, 4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl, 4-halo-5-difluoromethoxy-1-methylpyrazol-3-yl, a 3,4,5,6-tetrahydrophthalimid-1-yl, 8-thia-1,6-diazabicyclo 4.3.0!-nonane-7-on-9-iminoyl, 4-methyl-1,2,4-triazine-3,5-dion-2-yl, 3-chloro-4,5,6,7-tetrahydroindazol-2-yl, 1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazole-5-on-1-yl or a 5,6,7,8-tetrahydro-1,2,4-triazolo- 4,3-a!pyridin-3(2H)-on-2-yl moiety; Z is oxygen, sulfur or CH 2 ; n is 0 or 1, and W, X, Y, R, and R 1 are as described in the specification. Preferred are those compounds where W is oxygen; X is hydrogen or fluoro; Y is methyl or ethyl; n is 1; Z is oxygen; R is methyl; and R 1 is hydroxyalkyl or CH 2 OCONHCH 3 .

We claim: 
     
       1. A compound having the formula ##STR24## where Q is ##STR25## W is oxygen or sulfur; X is hydrogen, halogen, or lower alkyl; Y is hydrogen, halogen, straight or branched chain lower alkyl, haloalkyl, alkoxy, alkenyl, phenyl, or phenoxy;   n is 0 or 1;   Z is oxygen, sulfur, or CH 2  ;   R is hydrogen, halogen, or lower alkyl;   R 1  is cyano, hydroxyalkyl, alkoxyalkyl, dialkoxyalkyl, trialkylsilyloxyalkyl, formyl, carboxyl, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, alkylcarbonyloxyalkyl, alkoxycarbonyloxyalkyl, alkylcarbonylaminoalky, alkoxycarbonylaminoalkyl, alkylsulfonylaminoalkyl, alkyaminocarbonyloxyalkyl, arylaminocarbonyloxyalkyl, alkoxyiminoalkyl, epoxy, 1,3-dioxan-4-yl, or 2,2-dialkyl-1,3-dioxolan-4-yl;   R 2  is hydrogen, amino, straight or branched chain alkyl, haloalkyl, cyanoalkyl, alkoxyalkyl, arylalkyl, alkoxycarbonylalkyl, alkenyl, alkynyl, or sodium salt; and   R 3  is halogen; with the proviso that when Z is oxygen and n is 1, R 1  is other than alkoxycarbonyl, aminocarbonyl, or alkylcarbonyl.   
     
     
       2. The compound of claim 1 where Q is 1-substituted-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl. 
     
     
       3. The compound of claim 1 where Q is 4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl. 
     
     
       4. The compound of claim 1 where Q is 4-halo-5-difluoromethoxy-1-methylpyrazol-3-yl. 
     
     
       5. The compound of claim 1 where Q is 3,4,5,6-tetrahydrophthalimid-1-yl. 
     
     
       6. The compound of claim 1 where Q is 8-thia-1,6-diazabicyclo 4.3.0!-nonane-7-on-9-iminoyl. 
     
     
       7. The compound of claim 1 where Q is 4-methyl-1,2,4-triazine-3,5-dion-2-yl. 
     
     
       8. The compound of claim 1 where Q is 3-chloro-4,5,6,7-tetrahydroindazol-2-yl. 
     
     
       9. The compound of claim 1 where Q is 1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazole-5-on-1-yl. 
     
     
       10. The 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. 
     
     
       11. The compound of claim 1 where W is oxygen; X is hydrogen or fluoro; Y is methyl or ethyl; n is 1; Z is oxygen; R is methyl; and R 1  is hydroxyalkyl or CH 2  OCONHCH 3 . 
     
     
       12. The compound of claim 1 where Q is 1-substituted-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl; W is oxygen; X is hydrogen or fluoro; Y is methyl or ethyl; n is 1; Z is oxygen; R is methyl; R 1  is hydroxyalkyl or CH 2  OCONHCH 3  ; and R 2  is methyl or amino. 
     
     
       13. The compound of claim 12 where R 1  is CH 2  OH, C(CH 3 ) 2  OH, or CH 2  OCONHCH 3 . 
     
     
       14. A compound having the formula ##STR26## where Y is hydrogen, halogen, straight or branched chain lower alkyl, haloalkyl, alkoxy, alkenyl, phenyl, or phenoxy; U is formyl or CH 2  -T;   T is chloro, bromo, hydroxy, or 1,1-dimethylethyldimethylsilyloxy;   n is 1;   Z is oxygen;   R is hydrogen, halogen, or lower alkyl; and   R 1  is cyano, hydroxyalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkoxycarbonyl, 1,1-dimethylethyldimethylsilyloxyalkyl, 2,2-dimethyl-1,3-dioxolan-4-yl, or 1,3-dioxan-4-yl; with the proviso that when Y is methyl, U is formyl, and R is hydrogen, R 1  is other than alkoxyalkyl.     
     
     
       15. An herbicidal composition comprising an herbicidally effective amount of a compound of claim 1, and an herbicidally compatible carrier therefor. 
     
     
       16. An herbicidal composition comprising an herbicidally effective amount of a compound of claim 1 and an herbicidally effective amount of another herbicide. 
     
     
       17. The herbicidal composition of claim 16 further comprising an herbicidally compatible carrier therefor. 
     
     
       18. A method of controlling undesired plant growth, comprising application of an herbicidally effective amount of a composition of claim 16 to a locus where the undesired plants are growing or are expected to grow. 
     
     
       19. A method of controlling undesired plant growth, comprising application of an herbicidally effective amount of a composition of claim 17 to the locus where the undesired plants are growing or are expected to grow. 
     
     
       20. A method of controlling undesired plant growth, comprising application of an herbicidally effective amount of a composition of claim 15 to a locus where the undesired plants are growing or are expected to grow.