Herbicidal heterocyclyl-spirobicyclic catechols

Abstract

It has now been found that certain heterocyclyl-spirobicyclic catechols are useful as pre-emergent and post-emergent herbicides. These compounds are represented by formula II: ##STR1## where Q is a 1-substituted-6-trifluoromethyl-2,4 (1H,3H)-pyrimidinedion-3-yl, a 3,4,5,6-tetrahydrophthalimid-1-yl, a 5,6,7,8-tetrahydro-1H,3H- 1,3,4!thiadiazolo 3,4-a!pyridazineimin-1-yl, or a 1,6,8-triazabicyclo 4.3.0!-nonane-7,9-dion-8-yl; and A, B, X, Y, Z, n, u and R are as described in the specification. Preferred are those compounds where A and B are oxygen; Y is chlorine; Z is fluorine; n is 1 when u is 1 or n is 2 when u is 0; and X is oxygen.

We claim: 
     
       1. A compound having the formula ##STR13## where Q is ##STR14## A and B are independently selected from oxygen or sulfur; u isO or 1; nis1to6;   Y is hydrogen, halogen, cyano, alkyl, or haloalkyl;   Z is hydrogen or halogen;   R is hydrogen, amino, straight or branched chain alkyl, haloalkyl, cyanoalkyl, alkoxyalkyl, arylalkyl, alkoxycarbonylalkyl, alkenyl, alkynyl, or a salt-forming ion; and when u is 1, X is selected from oxygen, sulfur, or -N(alkyl)-.     
     
     
       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 3,4,5,6-tetrahydrophthalimid-1-yl. 
     
     
       4. A compound of claim 1 where Q is 2- 5,6,7,8-tetrahydro-9-oxo-1H,3H- 1,3,4!thiadiazolo 3,4-a!pyridazineiminyl!. 
     
     
       5. A compound of claim 1 where Q is 1,6,84riazabicyclo 4.3.0!-nonane-7,9-dion-8-yl. 
     
     
       6. A compound of claim 1 where A and B are oxygen; Y and Z are halogen; n is 1 when u is 1 or n is 2 when u is 0; and X is oxygen. 
     
     
       7. A compound of claim 6 where Y is chlorine and Z is fluorine. 
     
     
       8. A compound of claim 7 where Q is 1-substituted-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl or 3,4,5,6-tetrahydrophthalimid-1 -yl; and R is methyl or amino. 
     
     
       9. A compound of claim 8 where Q is 1-substituted-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl. 
     
     
       10. A compound of claim 9 where X is oxygen and R is methyl. 
     
     
       11. An herbicidal composition comprising an herbicidally effective amount of a compound of claim 1, and an herbicidally compatible carrier therefor. 
     
     
       12. 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, fluroxypyr, molinate, EPTC, trifluralin, pendimethalin, metribuzin, atrazine, paraquat, sethoxydim, clethodim, clomazone, glufosinate, diflufenican, and isoxaflutole. 
     
     
       13. An composition of claim 12, and an herbicidally compatible carrier therefor. 
     
     
       14. 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. 
     
     
       15. 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 13.