Abstract:
Substituted tetrahydro-1H-[1,2,4]-triazolo[1,2-a]pyridazine-1,3(2H)-dione herbicides of Formula I provide broad spectrum weed control in citrus, sugarcane, coffee, oil palm, grapes and nut trees

Description:
CROSS-REFERENCE TO RELATED APPLICATION 
     This is a continuation of U.S. application Ser. No. 08/090,150, filed under 35 USC 371 on Jul. 28, 1993, now abandoned, which is a continuation of PCT/US92/00360, filed Jan. 29, 1992, which is a continuation-in-part of U.S. application Ser. No. 07/649,355, filed Feb. 1, 1991, now abandoned. 
    
    
     BACKGROUND OF THE INVENTION 
     The compounds of the instant invention are known for use as herbicides. Such disclosure is found in EP-A-075,267 and U.S. Pat. No. 4,881,967. There are, however, no teachings for the use of such herbicides in selected crops such as citrus, sugarcane, coffee, banana, oil palm, loblolly pine, rubber, cocoa, grapes, plantain, pineapple, fruit trees such as apples, nut trees, and turf grass such as Kentucky bluegrass. These crops are important markets and are cultivated particularly in regions of the Pacific rim and South America. Citrus, turf grass and loblolly pine also are grown elsewhere. 
     The yields of selected crops such as citrus, sugarcane, coffee, banana, oil palm, loblolly pine, rubber, cocoa, grapes, fruit trees, Kentucky bluegrass, and Bermudagrass tend to be lessened by undesired plants such as crabgrass, guineagrass, itchgrass and the like. In addition, the yields of these crops tend to be reduced by crop plants such as corn, cotton, wheat, rice, and the like. A need therefore exists for controlling these types of plantings to improve the yields of selected crops such as those mentioned above. 
     SUMMARY OF THE INVENTION 
     This invention comprises the use of the compound of Formula I ##STR1## wherein 
     R is isopropyl, allyl, propargyl or --CH(CH 3 )C═CH; 
     X is Cl or Br; 
     Y is F or Cl; 
     Z is H or can be taken together with R as ##STR2## such that the linking oxygen is attached to the methine carbon; and its agriculturally suitable salts for broad spectrum weed control in selected crops such as citrus, sugarcane, coffee, banana, oil palm, loblolly pine, rubber, cocoa, grapes, plantain, pineapple, fruit trees such as apples, nut trees, turf grass such as Kentucky bluegrass, and the like. 
     Preferred for reasons of more efficient weed control and/or better crop tolerance, the method of the invention for controlling undesired plantings in selected crops such as, citrus, sugarcane, coffee, banana, oil palm, loblolly pine, rubber, cocoa, grapes, plantain, pineapple, fruit trees such as apples, nut trees, and turf grass such as Kentucky bluegrass and the like comprises applying to the locus of the undesired plantings in these crops a herbicidally effective amount of a compound of Formula I wherein X is Cl, Y is F and Z is H. Preferably, the crop selected is chosen from the group of citrus, sugarcane, coffee, banana, oil palm and loblolly pine. More preferably, the compound of Formula I is either 2-[4-chloro-2-fluoro-5-[(2-pyropynyl)oxy]-phenyl]tetrahydro-1H-[1,2,4]-triazolo[1,2-a]pyridazine -1,3(2H)-dione or 2-(7-chloro-5-fluoro-2,3-dihydro-2-methyl-4-benzofuranyl)tetrahydro-1H-[1,2,4]triazolo-[1,2-a]pyridazine-1,3(2H)-dione. 
    
    
     DETAILED DESCRIPTION OF THE INVENTION 
     Having briefly summarized the invention, the invention will now be described in detail by reference to the following specification and non-limiting examples. Unless otherwise specified, all percentages are by weight. 
     Synthesis 
     The compounds of Formula I can be prepared according to the procedures of EP-A-075,267 and U.S. Pat. No. 4,881,967, the disclosures of which are herein incorporated by reference. 
     Particularly important compounds of Formula I for use in this invention include the following: 
     
         ______________________________________ ##STR3##X      Y      Z            R______________________________________Cl     Cl     H            CH.sub.2 CCHCl     Cl     H            CH.sub.2 CHCH.sub.2Cl     Cl     H            CH(CH.sub.3)CCHCl     Cl     H            CH(CH.sub.3).sub.2Cl     Cl          ##STR4##Cl     F      H            CH.sub.2 CCHCl     F      H            CH.sub.2 CHCH.sub.2Cl     F      H            (CH.sub.3)CCHCl     F      H            CH(CH.sub.3).sub.2Cl     F          ##STR5##Br     Cl     H            CH.sub.2 CCHBr     Cl     H            CH.sub.2 CHCH.sub.2Br     Cl     H            CH(CH.sub.3)CCHBr     Cl     H            CH(CH.sub.3).sub.2Br     Cl          ##STR6##Br     F      H            CH.sub.2 CCHBr     F      H            CH.sub.2 CHCH.sub.2Br     F      H            CH(CH.sub.3)CCHBr     F      H            CH(CH.sub.3).sub.2Br     F          ##STR7##______________________________________ 
    
     Formulations 
     Useful formulations of the compounds of Formula I can be prepared in well known forms such as dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. 
     The methods of making such formulations are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, &#34;Agglomeration&#34;, Chemical Engineering, Dec. 4, 1967, pp. 147ff. and &#34;Perry&#39;s Chemical Engineer&#39;s Handbook&#34;, 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff. 
     For further information regarding the art of formulation, see for example: 
     H. M. Loux U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41; 
     R. W. Luckenbaugh U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; 
     H. Gysin and E. Knusli U.S. Pat. No. 2,891,855, Jun. 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; 
     G. C. Klingman, &#34;Weed Control as a Science&#34;, John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and 
     J. D. Fryer and S. A. Evans, &#34;Weed Control Handbook&#34;, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103. 
     Many of these forms of the compounds of Formula I may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). More specifically, they typically contain these ingredients in the following approximate proportions: 
     
         ______________________________________       Weight Percent*         ActiveFormulation   Ingredient                   Diluent(s)                             Surfactant(s)______________________________________Wettable Powders         20-90      0-74     1-10Oil Suspensions,          3-50     40-95     0-15Emulsions,Solutions, (includingEmusifiable Concen-trates)Aqueous Suspension         10-50     40-84     1-20Dusts          1-25     70-99     0-5Granules and  0.1-95      5-99.9  0-15PelletsHigh Strength 90-99      0-10     0-2Compositions______________________________________ *Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent. 
    
     Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing. 
     Typical solid diluents that may be included in the formulation are described in Watkins, et al., &#34;Handbook of Insecticide Dust Diluents and Carriers&#34;, 2nd Ed., Dorland Books, Caldwell, N. J., but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powder formulations and the denser diluents for dust formulations. 
     Typical liquid diluents and solvents that may be included in the formulations are described in Marsden, &#34;Solvents Guide&#34;, 2nd Ed., Interscience, New York, 1950. Solubility of the liquid diluent of under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0° C. &#34;McCutcheon&#39;s Detergents and Emulsifiers Annual&#34;, MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, &#34;Encyclopedia of Surface Active Agents&#34;, Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc. 
     In the following examples of the formulation of the compound of Formula I, all parts are by weight unless otherwise indicated. 
     Example A 
     
         ______________________________________2-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-                      80%tetrahydro-1H-[1,2,4]-triazolo[1,2-a]pyridazine-1,3(2H)-dionesodium alkylnaphthalenesulfonate                      2%sodium ligninsulfonate     2%synthetic amorphous silica 3%kaolinite                  13%______________________________________ 
    
     The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged. 
     Example B 
     
         ______________________________________2-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-                      50%tetrahydro-1H-[1,2,4]-triazolo[1,2-a]pyridazine-1,3(2H)-dionesodium alkylnaphthalenesulfonate                       2%low viscosity methyl cellulose                       2%diatomaceous earth         46%______________________________________ 
    
     The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging. 
     Example C 
     
         ______________________________________Wettable Powder of Example B                   5%attapulgite granules   95%(U.S.S. 20-40 mesh; 0.84-0.42 mm)______________________________________ 
    
     A slurry of wettable powder containing 25% solids is sprayed onto the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged. 
     Example D 
     
         ______________________________________2-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-                      25%tetrahydro-1H-[1,2,4]-triazolo[1,2-a]pyridazine-1,3(2H)-dioneanhydrous sodium sulfate   10%crude calcium ligninsulfonate                       5%sodium alkylnaphthalenesulfonate                       1%calcium/magnesium bentonite                      59%______________________________________ 
    
     The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders and about 3 mm diameter which are cut to produce pellets about 3 mm long. These pellets may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled. 
     Example E 
     
         ______________________________________2-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-                      1%tetrahydro-1H-[1,2,4]-triazolo[1,2-a]pyridazine-1,3(2H)-dioneN,N-dimethylformamide      9%attapulgite granules       90%(U.S.S. 20 to 40 sieve)______________________________________ 
    
     The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged. 
     Example F 
     
         ______________________________________2-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-                      80%tetrahydro-1H-[1,2,4]-triazolo[1,2-a]pyridazine-1,3(2H)-dionewetting agent               1%crude ligninsulfonate salt (containing                      10%(containing 5-20% of the natural sugars)attapulgite clay            9%______________________________________ 
    
     The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%. The material then is discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use. 
     Example G 
     
         ______________________________________2-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-                      40%tetrahydro-1H-[1,2,4]-triazolo[1,2-a]pyridazine-1,3(2H)-dionepolyacrylic acid thickener 0.3%dodecylphenol polyethylene glycol ether                      0.5%disodium phosphate         1%monosodium phosphate       0.5%polyvinyl alcohol          1.0%water                      56.7%______________________________________ 
    
     The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size. 
     Example H 
     
         ______________________________________2-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-                      99%tetrahydro-1H-[1,2,4]-triazolo[1,2-a]pyridazine-1,3(2H)-dionesilica aerogel             0.5%synthetic amorphous silica 0.5%______________________________________ 
    
     The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary. 
     Example I 
     
         ______________________________________2-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-                      90%tetrahydro-1H-[1,2,4]-triazolo[1,2-a]pyridazine-1,3(2H)-dionedioctyl sodium sulfosuccinate                      0.1%synthetic fine silica      9.9%______________________________________ 
    
     The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100  microns. The material is sifted through a U.S.S. No. 50 screen and then packaged. 
     Example J 
     
         ______________________________________2-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-                      40%tetrahydro-1H-[1,2,4]-triazolo[1,2-a]pyridazine-1,3(2H)-dionesodium ligninsulfonate     20%montmorillonite clay       40%______________________________________ 
    
     The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged. 
     Example K 
     
         ______________________________________2-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-                      35%tetrahydro-1H-[1,2,4]-triazolo[1,2-a]pyridazine-1,3(2H)-dioneblend of polyalcohol carboxylic esters                       6%and oil soluble petroleum sulfonatesxylene                     59%______________________________________ 
    
     The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water. 
     Example L 
     
         ______________________________________2-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-                      10%tetrahydro-1H-[1,2,4]-triazolo[1,2-a]pyridazine-1,3(2H)-dioneattapulgite                10%Pyrophyllite               80%______________________________________ 
    
     The active ingredient is blended with attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous. 
     Example M 
     
         ______________________________________2-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-                      25%tetrahydro-1H-[1,2,4]-triazolo[1,2-a]pyridazine-1,3(2H)-dionepolyoxyethylene sorbitol hexaoleate                       5%highly aliphatic hydrocarbon oil                      70%______________________________________ 
    
     The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water. 
     The compounds that are employed in the present invention surprisingly are active herbicides for selective and/or general broadleaf and grass weeds control in crops including coffee, cocoa, oil palm, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, rubber, pineapple and loblolly pine. 
     The compounds of Formula I can be applied as a preemergence or postemergence treatment using techniques such as banding, directed sprays, or broadcast applications. By selecting the appropriate rate which would be apparent to one skilled in the art, the compounds of Formula I can be used in areas where control of vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, oil well sites, drive-in theaters, around billboards, highway and railroad structures and in fence rows. Alternatively, by selecting the proper rates, adjuvants and application methods, the compounds of Formula I can be used for selective weed control in plantation crops such as citrus, sugarcane, coffee, oil palm, rubber, cocoa, grapes, fruit trees, pineapple, and turf species such as Kentucky bluegrass. In general, the compounds of this invention are used at 5 to 5000 g/ha with a preferred rate range of 10 to 2000 g/ha rate. One skilled in the art can select the proper rates for a given situation. 
     The compounds of Formula I also may be used in combination with other herbicides. The compounds of Formula I are particularly useful in combinations with other herbicides for total vegetation control in plantation crops. Examples of other herbicides that may be employed with the compounds of Formula I include, but are not limited to, triazine, triazole, uracil, urea, amide, carbamate, bipyridylium, phenoxy, sulfonylurea and imidazole types, as well as with mefluidide, glyphosate or gluphosinate. Additional examples of herbicides that may be employed with the compounds of Formula I are shown in Table I. 
     
                       TABLE I______________________________________Common Name     Chemical Name______________________________________acetochlor     2-chloro-N-(ethoxymethyl)-N-     (2-ethyl-6-methylphenyl)acetamideacifluorfen     5-[2-chloro-4-(trifluoromethyl)-     phenoxy]-2-nitrobenzoic acidacrolein  2-propenalalachlor  2-chloro-N-(2,6-diethylphenyl)-N-     (methoxymethyl)acetamideanilofos  S-4-chloro-N-isopropylcarbaniloyl-     methyl-O,O-dimethyl phosphorodi-     thioateametryn   N-ethyl-N&#39;-(1-methylethyl)-6-     (methylthio)-1,3,5-triazine-2,4-     diamineamitrole  1H-1,2,4-triazol-3-amineAMS       ammonium sulfamateasulam    methyl [(4-aminophenyl)sulfonyl]-     carbamateatrazine  6-chloro-N-ethyl-N&#39;-(1-methylethyl)-     1,3,5-triazine-2,4-diaminebarban    4-chloro-2-butynyl 3-chlorocarbamatebenefin   N-butyl-N-ethyl-2,6-dinitro-4-(tri-     fluoromethyl)benzenaminebensulfuron     2-[[[[[(4,6-dimethoxy-2-pyrimi-methyl    dinyl)amino]methylcarbonyl]-     amino]sulfonyl]methyl]benzoic     acid, methyl esterbensulide O,O-bis(1-methylethyl) S-[2-     [(phenylsulfonyl)amino]-     ethyl]phosphorodithioatebentazon  3-(1-methylethyl)-(1H)-2,1,3-     benzothiadiazin-4(3H)-one,     2,2-dioxidebenzofluor     N-[4-(ethylthio)-2-(trifluoro-     methyl)phenyl]methanesulfonamidebenzoylprop     N-benzoyl-N-(3,4-dichlorophenyl)-DL-     alaninebifenox   methyl 5-(2,4-dichlorophenoxy)-2-     nitrobenzoatebromacil  5-bromo-6-methyl-3-(1-methylpropyl)-     2,4 (1H, 3H) pyrimidinedionebromoxynil     3,5-dibromo-4-hydroxybenzonitrilebutachlor N-(butoxymethyl)-2-chloro-N-(2,6-     diethylphenyl)acetamidebuthidazole     3-[5-(1,1-dimethylethyl)-1,3,4-thia-     diazol-2-yl]-4-hydroxy-1-methyl-2-     imidazolidinonebutralin  4-(1,1-dimethylethyl)-N-(1-methyl-     propyl)-2,6-dinitrobenzenaminebutylate  S-ethyl bis(2-methylpropyl)-     carbamothioatecacodylic dimethyl arsinic oxideacidCDAA      2-chloro-N,N-di-2-propenylacetamideCDEC      2-chloroallyl diethyldithiocarbamateCGA 142,464     3-(4,6-dimethoxy-1,3,5-triazin-2-yl)-     1-[2-(2-methoxyethoxy)-pehnyl-     sulfonyl]-ureachloramben     3-amino-2,5-dichlorobenzoic acidchlorbromuron     3-(4-bromo-3-chlorophenyl)-1-methoxy-1-     methylureachlorimuron     2-[[[[(4-chloro-6-methoxy-2-pyrimi-ethyl     dinyl)ethylamino]carbonyl]-     amino]sulfonyl]benzoic     acid, ethyl esterchlormethoxy-     2,4-dichlorophenyl 4-nitro-3-nil       methoxyphenyl etherchlornitrofen     2,4,6-trichlorophenyl-4-nitro-     phenyl etherchloroxuron     N&#39;-[4-(4-chlorophenoxy)phenyl]-N,N-     dimethylureachlorpropham     1-methylethyl 3-chlorophenylcarbamatechlorsulfuron     2-chloro-N-[[(4-methoxy-6-methyl-1,3,5-     triazin-2-yl)amino]carbonyl)benzene-     sulfonamidechlortoluron     N&#39;-(3-chloro-4-methylphenyl)-N,N-     dimethylureacinmethylin     exo-1-methyl-4-(1-methylethyl)-2-[(2-     methylphenyl)methoxy]-7-oxabicyclo-     [2.2.1]heptaneclethodim (E,E)-(±)-2-[1[[(3-chloro-2-propenyl)-     oxy]imino]propyl]-5-[2-(ethylthio)-     propyl]-3-hydroxy-2-cyclohexen-1-oneclomazone 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-     3-isoxazolidinonecloproxydim     (E,E)-2-[1-[[(3-chloro-2-propenyl)oxy)-     imino]butyl]-5-[2-(ethylthio)propyl]-     3-hydroxy-2-cyclohexen-1-oneclopyralid     3,6-dichloro-2-pyridinecarboxylic acidCMA       calcium salt of MAAcyanazine 2-[[4-chloro-6-(ethylamino)-1,3,5-tri-     azin-2-yl]amino]-2-methylpropanenitrilecycloate  S-ethyl cyclohexylethylcarbamothioatecycluron  3-cyclooctyl-1,1-dimethylureacyperquat 1-methyl-4-phenylpyridiniumcyprazine 2-chloro-4-(cyclopropylamino)-6-(iso-     propylamino)-s-triazinecyprazole N-[5-(2-chloro-1,1-dimethylethyl)-1,3,4-     thiadiazol-2-yl]cyclopropanecarbox-     amidecypromid  3&#39;,4&#39;-dichlorocyclopropanecarboxanilidedalapon   2,2-dichloropropanoic aciddazomet   tetrahydro-3,5-dimethyl-2H-1,3,5-thia-     diazine-2-thioneDCPA      dimethyl 2,3,5,6-tetrachloro-1,4-benzene-     dicarboxylatedesmediphan     ethyl [3-[[(phenylamino)carbonyl]oxy]-     phenyl]carbamatedesmetryn 2-(isopropylamino)-4-(methylamino)-6-     (methylthio)-s-triazinediallate  S-(2,3-dichloro-2-propenyl)bis(1-     methylethyl)carbamothioatedicamba   3,6-dichloro-2-methoxybenzoic aciddichlobenil     2,6-dichlorobenzonitriledichlorprop     (±)-2-(2,4-dichlorophenoxy)propanoic     aciddichlofop (±)-2-[4-(2,4-dichlorophenoxy)phenoxy]-     propanoic acid, methyl esterdiethatyl N-(chloroacetyl)-N-(2,6-diethylphenyl)-     glycinedifenzoquat     1,2-dimethyl-3,5-diphenyl-1H-pyrazoliumdimepiperate     S-1-methyl-1-phenylethylpiperidine-     1-carbothioatedinitramine     N.sup.3,N.sup.3 -diethyl-2,4-dinitro-6-(trifluoro-     methyl)-1,3-benzenediaminedinoseb   2-(1-methylpropyl)-4,6-dinitrophenoldiphenamid     N,N-dimethyl-a-phenylbenzeneacetamidedipropetryn     6-(ethylthio)-N,N&#39;-bis(1-methylethyl)-     1,3,5-triazine-2,4-diaminediquat    6,7-dihydrodipyrido[1,2-a:2&#39;,1&#39;-c]-     pyrazinedium iondiuron    N&#39;-(3,4-dichlorophenyl)-N,N-dimethylureaDNOC      2-methyl-4,6-dinitrophenolDSMA      disodium malt of MAAdymron    N-(4-methylphenyl)-N&#39;-(1-methyl-     1-phenylethyl)ureaendothall 7-oxabicyclo[2.2.1]heptane-2,3-dicarbox-     ylic acidEPTC      S-ethyl dipropylcarbamothioateesprocarb S-benzyl-N-ethyl-N-(1,2-dimethyl)-     propyl)thiolcarbamateethalfluralin     N-ethyl-N-(2-methyl-2-propenyl)-2,6-     dinitro-4-(trifluoromethyl)-     benzenamineethofumesate     (±)-2-ethoxy-2,3-dihydro-3,3-dimethyl-     5-benzofuranyl methanesulfonateExpress ®     2-[[[[N-(4-methoxy-6-methyl-1,3,5-     triazine-2-yl)-N-methylamino]-     carbonyl]amino]sulfonyl]benzoic     acid, methyl esterfenac     2,3,6-trichlorobenzenacetic acidfenoxaprop     (±)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]-     phenoxy]propanoic acidfenuron   N,N-dimethyl-N&#39;-phenylureafenuron TCA     Salt of fenuron and TCAflamprop  N-benzoyl-N-(3-chloro-4-fluorophenyl)-     DL-alaninefluazifop (±)-2-[4-[[5-(trifluoromethyl)-2-pyri-     dinyl]oxy]phenoxy]propanoic acidfluazifop-P     (R)-2-[4-[[5-(trifluoromethyl)-2-pyri-     dinyl]oxy]phenoxy]propanoic acidfluchloralin     N-(2-chloroethyl)-2,6-dinitro-N-propyl-     4-(trifluoromethyl)benzenaminefluometuron     N,N-dimethyl-N&#39;-[3-(trifluoromethyl)-     phenyl]ureafluorochlor-     3-chloro-4-(chloromethyl)-1-[3-(tri-idone     fluoromethyl)phenyl]-2-pyrrolidinefluorodifen     p-nitrophenyl a,a,a-trifluoro-2-nitro-     p-tolyl etherfluorogly-     carboxymethyl 5-[2-chloro-4-(tri-cofen     fluoromethyl)phenoxy]-2-nitrobenzoatefluridone 1-methyl-3-phenyl-5-[3-(trifluoro-     methyl)phenyl]-4(1H)-pyridinonefomesafen 5-[2-chloro-4-(trifluoromethyl)phenoxy]-     N-(methylsulfonyl)-2-nitrobenzamidefosamine  ethyl hydrogen (aminocarbonyl)-     phosphateglyphosate     N-(phosphonomethyl)glycinehaloxyfop 2-[4-[[3-chloro-5-(trifluoromethyl)-2-     pyridinyl]oxy]phenoxy]propanoic acidHarmony ®     3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-     2-yl)amino]carbonyl]amino]sulfonyl]-     2-thiophenecarboxylic acid, methyl     esterhexaflurate     potassium hexafluoroarsenatehexazinone     3-cyclohexyl-6-(dimethylamino)-1-methyl-     1,3,5-triazine-2,4(1H,3H)-dioneimazametha-     6-(4-isopropyl-4-methyl-5-oxo-2-benz      imidazolin-2-yl)-m-toluic acid,     methyl ester and 6-(4-isopropyl-     4-methyl-5-oxo-2-imidazolin-2-yl)-     p-toluic acid, methyl esterimazapyr  (±)-2-[4,5-dihydro-4-methyl-4-(1-methyl-     ethyl)-5-oxo-1H-imidazole-2-yl]-3-     pyridinecarboxylic acidimazaquin 2-[4,5-dihydro-4-methyl-4-(1-methyl-     ethyl)-5-oxo-1H-imidazole-2-yl]-3-     quinolinecarboxylic acidimazethapyr     (±)-2-[4,5-dihydro-4-methyl-4-(1-methyl-     ethyl)-5-oxo-1H-imidazole-2-yl]  -5-     ethyl-3-pyridinecarboxylic acidioxynil   4-hydroxy-3,5-diiodobenzonitrileisopropalin     4-(1-methylethyl)-2,6-dinitro-N,N-     dipropylbenzenamineisoproturon     N-(4-isopropylphenyl)-N&#39;N&#39;-dimethylureaisouron   N&#39;-[5-(1,1-dimethylethyl)-3-isoxazolyl]-     N,N-dimethylureaisoxaben  N-[3-(1-ethyl-1-methylpropyl)-5-     isoxazolyl]-2,6-dimethoxybenzamidekarbutilate     3-[[(dimethylamino)carbonyl]amino]-     phenyl-(1,1-dimethylethyl)carbamatelactofen  (±)-2-ethoxy-1-methyl-2-oxoethyl 5-[2-     chloro-4-(trifluoromethyl)phenoxy]-     2-nitrobenzoatelenacil   3-cyclohexyl-6,7-dihydro-1H-cyclopenta-     pyrimidine-2,4(3H,5H)-dionelinuron   N&#39;-(3,4-dichlorophenyl)-N-methoxy-N-     methylureaMAA       methylarsonic acidMAMA      monoammonium salt of MAAMCPA      (4-chloro-2-methylphenoxy)acetic acidMCPB      4-(4-chloro-2-methylphenoxy)butanoic     acidMON 7200  S,S-dimethyl-2-(difluoromethyl)-4-     (2-methylpropyl)-6-(trifluoromethyl)-     3,5-pyridinedicarbothionatemecoprop  (±)-2-(4-chloro-2-methylphenoxy)-     propanoic acidmefenacet 2-(2-benzothiazolyloxy-N-methyl-N-     phenylacetamidemefluidide     N-[2,4-dimethyl-5-[[(trifluoromethyl)-     sulfonyl]amino]phenyl]acetamidemethal-   N-(2-methyl-2-propenyl)-2,6-dinitro-N-propalin  propyl-4-(trifluoromethyl)benzenamidemethabenz-     1,3-dimethyl-3-(2-benzothiazolyl)ureathiazuronmetham    methylcarbamodithioic acidmethazole 2-(3,4-dichlorophenyl)-4-methyl-1,2,4-     oxadiazolidine-3,5-dionemethoxuron     N&#39;-(3-chloro-4-methoxyphenyl)-N,N-     dimethylureametolachlor     2-chloro-N-(2-ethyl-6-methylphenyl)-N-     (2-methoxy-1-methylethyl)acetamidemetribuzin     4-amino-6-(1,1-dimethylethyl)-3-(methyl-     thio)-1,2,4-triazin-5(4H)-onemetsulfuron     2-[[[[(4-methoxy-6-methyl-1,3,5-tri-methyl    azin-2-yl) amino]carbonyl]-     amino]sulfonyl]benzoic acid,     methyl esterMH        1,2-dihydro-3,6-pyridazinedionemolinate  S-ethyl hexahydro-1H-azepine-1-carbo-     thioatemonolinuron     3-(p-chlorophenyl)-1-methoxy-1-methyl-     ureamonuron   N&#39;-(4-chlorophenyl)-N,N-dimethylureamonuron TCA     Salt of monuron and TCAMSMA      monosodium salt of MAAnapropamide     N,N-diethyl-2-(1-naphthalenyloxy)-     propanamidenaptalam  2-[(1-naphthalenylamino)carbonyl]-     benzoic acidneburon   2-butyl-3-(3,4-dichlorophenyl)-1-methyl-     ureanitralin  4-(methylsulfonyl)-2,6-dinitro-N,N-     dipropylanilinenitrofen  2,4-dichloro-1-(4-nitrophenoxy)benzenenitrofluorfen     2-chloro-1-(4-nitrophenoxy)-4-(tri-     fluoromethyl)benzenenorea     N,N-dimethyl-N&#39;-(octahydro-4,7-methano-     1H-inden-5-yl)urea 3aa,-     4a,5a,7a,7aa-isomernorflurazon     4-chloro-5-(methylamino)-2-[3-(tri-     fluoromethyl)phenyl]-3(2H)-     pyridazinoneoryzalin  4-(dipropylamino)-3,5-dinitro-     benzenesulfonamideoxadiazon 3-[2,4-dichloro-5-(1-methylethoxy)-     phenyl]-5-(1,1-dimethylethyl)-     1,3,4-oxadiazol-2(3H)-oneoxyfluorfen     2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-     (trifluoromethyl)benzeneparaquat  1,1&#39;-dimethyl-4,4&#39;-dipyridinium ionpebulate  S-propyl butylethylcarbamothioatependimethalin     N-(1-ethylpropyl)-3,4-dimethyl-2,6-     dinitrobenzenamineperfluidone     1,1,1-trifluoro-N-[2-methyl-4-(phenyl-     sulfonyl)phenyl]methanesulfonamidephenmedipham     3-[(methoxycarbonyl)amino]phenyl (3-     methylphenyl)carbamatepicloram  4-amino-3,5,6-trichloro-2-pyridine-     carboxylic acidPPG-1013  5-[2-chloro-4-(trifluoromethyl)-     phenoxy]-2-nitroacetophenone     oxime-O-acetic acid, methyl esterpretilachlor     α-chloro-2,6-diethyl-N-(2-propoxy-     ethyl)acetanilideprocyazine     2-[[4-chloro-6-(cyclopropylamino)-1,3,5-     triazine-2-yl]amino]-2-methylpropane-     nitrileprofluralin     N-(cyclopropylmethyl)-2,6-dinitro-N-     propyl-4-(trifluoromethyl)benzenamineprometon  6-methoxy-N,N&#39;-bis(1-methylethyl)-1,3,5-     triazine-2,4-diamineprometryn N,N&#39;-bis(1-methylethyl)-6-(methylthio)-     1,3,5-triazine-2,4-diaminepronamide 3,5-dichloro-N-(1,1-dimethyl-2-propyn-     yl)benzamidepropachlor     2-chloro-N-(1-methylethyl)-N-     phenylacetamidepropanil  N-(3,4-dichlorophenyl)propanamidepropazine 6-chloro-N,N&#39;-bis(1-methylethyl)-     1,3,5-triazine-2,4-diaminepropham   1-methylethyl phenylcarbamateprosulfalin     N-[[4-(dipropylamino)-3,5-dinitro-     phenyl]sulfonyl]-S,S-dimethylsulfil-     imineprynachlor     2-chloro-N-(1-methyl-2-propynyl)acet-     anilidepyrazolate     4-(2,4-dichlorobenzoyl)-1,3-dimethyl-     pyrazol-5-yl-p-toluenesulphonatepyrazon   5-amino-4-chloro-2-phenyl-3(2H)-     pyridazinonepyrazosulfuron     ethyl S-[3-(4,6-dimethoxypyrimidin-2-ethyl     yl)ureadosulfonyl]-1-methylpyrazole-     4-carboxylatequinclorac     3,7-dichloro-8-quinoline carboxylic acidquizalofop     (±)-2-[4-[(6-chloro-2-quinoxalinyl)-ethyl     oxy]phenoxy]propanoic acid, ethyl     estersecbumeton     N-ethyl-6-methoxy-N&#39;-(1-methylpropyl)-     1,3,5-triazine-2,4-diaminesethoxydim     2-[1-(ethoxyimino)butyl]-5-[2-(ethyl-     thio)propyl]-3-hydroxy-2-cyclohexon-     1-onesiduron   N-(2-methylcyclohexyl)-N&#39;-phenylureasimazine  6-chloro-N,N&#39;-diethyl-1,3,5-triazine-     2,4-diamineSK-233    1-(a,a-dimethylbenzyl)-3-(4-methyl-     phenyl)ureasulfometuron     2-[[[[(4,6-dimethyl-2-pyrimidinyl)-methyl    amino]carbonyl]amino]sulfonyl]-     benzoic acid, methyl esterTCA       trichloroacetic acidtebuthiuron     N-[5-(1,1-dimethylethyl)-1,3,4-thiadi-     azol-2-yl]-N,N&#39;-dimethylureaterbacil  5-chloro-3-(1,1-dimethylethyl)-6-     methyl-2,4(1H,3H)-pyrimidinedioneterbuchlor     N-(butoxymethyl)-2-chloro-N-[2-(1,1-     dimethylethyl)-6-methylphenyl]-     acetamideterbuthyl-     2-(tert-butylamino)-4-chloro-6-(ethyl-azine     amino)-s-triazineterbutol  2,6-di-tert-butyl-p-tolyl methylcar-     bamateterbutryn N-(1,1-dimethylethyl)-N&#39;-ethyl-6-     (methylthio)-1,3,5-triazine-     2,4-diaminethiobencarb     S-[(4-chlorophenyl)methyl] diethylcar-     bamothioatetriallate S-(2,3,3-trichloro-2-propenyl) bis(1-     methylethyl)carbamothioatetriclopyr [(3,5,6-trichloro-2-pyridinyl)-     oxy]acetic acidtridiphane     2-(3,5-dichlorophenyl)-2-(2,2,2-     trichloroethyl)oxiranetrifluralin     2,6-dinitro-N,N-dipropyl-4-(tri-     fluoromethyl)benzenaminetrimeturon     1-(p-chlorophenyl)-2,3,3-trimethylpseu-     dourea2,4-D     (2,4-dichlorophenoxy)acetic acid2,4-DB    4-(2,4-dichlorophenoxy)butanoic acidvernolate S-propyl dipropylcarbamothioatexylachlor 2-chloro-N-(2,3-dimethylphenyl)-N-     (1-methylethyl)acetamide______________________________________ 
    
     The herbicidal properties of the compounds of Formula I are evaluated as described below in the following tests. 
     As referred to in the tests below, Compound 1 means compounds of Formula I where R is (--CH 2  C═CH), X is Cl, Y is F, and Z is H. Compound 2 means compounds of Formula I where R and Z are taken together as ##STR8## such that the linking oxygen is attached to the methine carbine, Y is F, and X is Cl. Compound 2 has the following structure: ##STR9## Compound 4 means compounds of Formula I where R and Z are taken together as ##STR10## such that the linking oxygen is attached to the methine carbon, Y is Cl, and X is Cl. Compound 4 has the following structure: ##STR11## 
     TEST A 
     Plastic tray liners with individual planting compartments are filled with planting medium and seeded separately with bermudagrass (Cynodon dactylon), broadleaf signalgrass (Brachiaria platyphylla), guineagrass (Panicum maximum), smooth crabgrass (Digitaria ischaemum), barnyardgrass (Echinocloa crusgalli), large crabgrass (D. sanguinalis), johnsongrass (Sorghum halepense), Texas panicum (Panicum texanum), sandbur (Cenchrus echinatus), itchgrass (Rottboellia cochinchinensis), goosegrass (Eleusine indica), dallisgrass (Paspalum dilatatum), annual bluegrass (Poa annum), alfalfa (Medicago sativa), Pueraria javanica, morningglory (Ipomea spp.) purslane (Portulaca oleracea), field bindweed (Convolvulus arvensis), ragweed (Ambrosia elatior), peanut (Arachis hypogea), purple nutsedge (Cyperus rotundus), yellow nutsedge (C. esculeutus), and Kentucky bluegrass sod (Poa pratense). Sugarcane node cuttings are planted in 15.2 cm plastic pots filled with planting medium. 
     The plantings are treated preemergence and postemergence with the compounds formulated in a non-phytotoxic spray solution. Plantings are staggered so that the preemergence and postemergence treatments are sprayed on the same day. Plants are visually rated 18 to 29 days after treatment (DAT) and compared with appropriate controls. The injury ratings are based on the scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. A dash (--) indicates not determined. The results are shown in Tables Aa-Ab. 
     
                       TABLE Aa______________________________________     Compound 1     500  250    125    500  250  125     Preemergence                Postemergence                             g/ha______________________________________Sugarcane   --     --     --    30   10   0Bermudagrass       100    100    100  100   90  30Broadleaf   100    100    100  100  100  90signalgrassGuineagrass 100    100    100  100  100  100Smooth crabgrass       100    100    100  100   0    0Large crabgrass       100    100    100  100   90  90Johnson grass       100    100    100  100  100  100Texas panicum       100    100    100  100  100  100Sandbur      90    100     90  --   --   --Itchgrass   100    100    100  100   60  50Goosegrass  100    100    100  100  100  100Dallisgrass 100    100    100  100  100  90Annual bluegrass        80     60     40  100   80  20Kentucky bluegrass       --     --     --   100   0   10sodAlfalfa     100    100     90   90   20  30Pueraria javanica       100     90     90  --   --   --Morningglory       100    100    100  100  100  100Purslane    100    100    100  100  100  100Ragweed     100    100    100  100  100  100Peanut       70     70     60   80   30  60Purple nutsedge       --     --     --    80   50  20Yellow nutsedge       --     --     --    90   60  30______________________________________ 
    
     
                       TABLE Ab______________________________________       Compound 2       250       250       Preemergence                 Postemergence                             g/ha______________________________________Bermudagrass  100         0Broadleaf signalgrass         100         0Guineagrass   100         0Smooth crabgrass         100         0Large crabgrass         100         0Johnsongrass   90         0Texas panicum 100         0Sandbur       100         0Itchgrass      90         0Goosegrass    100         --Annual bluegrass          50         0Kentucky bluegrass sod         --          0Alfalfa       100         30Pueraria javanica          90         --Morningglory  100         60Purslane      100         100Ragweed       100         50Peanut         70         30Purple nutsedge          30         70Yellow nutsedge          60         60______________________________________ 
    
     TEST B 
     Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloa crus-galli), giant foxtail (Setaria faberi), wild oats (Avena fatua), cheatgrass (Bromus secalinus), velvetleaf (Abutilon theophrasti), morningglory (Ipomoea spp.), cocklebur (Xanthium pensylvanicum), sorghum, corn, soybean, sugarbeet, cotton, rice, wheat, barley, cassia and purple nutsedge (Cyperus rotundus) tubers are planted and treated preemergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crops and weed species are treated with a soil/foliage application. At the time of treatment, the plants ranged in height from 2 to 18 cm. Treated plants and controls are maintained in a greenhouse for sixteen days, after which all species are compared to controls and visually rated for response to treatment. The ratings, summarized in Tables Ba-Bc, are based on a numerical scale extending from 0=no injury, to 10=complete kill. The accompanying descriptive symbols have the following meanings: 
     C=chlorosis/necrosis 
     B=burn 
     D=defoliation 
     E=emergence inhibition 
     G=growth retardation 
     H=formative effect 
     U=unusual pigmentation 
     X=axillary stimulation 
     S=albinism 
     6Y=abscised buds or flowers 
     
                       TABLE Ba______________________________________     Compound 1     400   100      400     100     Preemergence                Postemergence                             g/ha______________________________________Corn         5C,9H   5C,9H    8B   6BSoybean     10C      3C,9H   10B   10BCotton      10C     10C      10B   10BSorghum     10C     10C      10B   9BMorningglory       10C     10C      10B   10BCrabgrass   10C      8C      10B   9BRice        10C      9C      10B   8BBarnyardgrass       10C     10C      10B   9BSpring wheat       10C     10C      10B   7BSugar beet  10C     10C      10B   10BWild oats   10C     10C      10B   8BNutsedge    10C     10C       9B   7BCocklebur   10C      9C      10B   10BCassia      10C     10C      10B   10B______________________________________ 
    
     
                       TABLE Bb______________________________________     Compound 2     400   50       400     50     Preemergence                Postemergence                            g/ha______________________________________Corn        10H     8H        9B    4B,7HSoybean     10H     10H      10B   10BCotton      10H     8H       10B   10BSorghum     10H     10H      10B    9BVelvetleaf  10H     10H      10B   10BMorningglory       10H     9H       10B   10BGiant foxtail       10H     9H       10B    9BCrabgrass   10H     9H       10B    9BRice        10H     9H       10B    9BBarnyardgrass       10H     7H       10B   10BSpring wheat        9H     7H       10B    8BWinter barley       10H     2H        9B    2BSugar beet  10H     10H      10B    9BWild oats    8H     4H       10B    5BNutsedge    10H     3H       10B    8BCheatgrass   6H     6H        4B,8H                               2BCocklebur   10H     7H        9B    7B______________________________________ 
    
     
                       TABLE Bc______________________________________     Compound 4     400    50      400     50     Preemergence                Postemergence                            g/ha______________________________________Corn         7C       0      6B    3BSoybean      2C,8G    0      8B    7BCotton       3C,7G    0      10B   10BSorghum     10C       3C     5B    2BVelvetleaf  10C      10C     10B   8BMorningglory        9C       2G     10B   5BGiant foxtail       10H       9H     9B    5BCrabgrass   10H       3C,8H  5B    1BRice         8C       2C     7B    3BBarnyardgrass        9H       0      9B    3BSpring wheat        3C,7H    0      6B    3BWinter barley        1C       0      4B    2BSugar beet   9C       7C     7B    6BWild oats    7C       3G     6B    3BNutsedge     8C       0      6B    1BCheatgrassCocklebur    2C       0      7B    4B______________________________________ 
    
     TEST C 
     Postemergence 
     Three round pans (25 cm diameter by 12.5 cm deep) are filled with Sassafras sandy loam soil. One pan is planted with nutsedge (Cyperus rotundus) tubers, crabgrass (Digitaria sanguinalis), sicklepod (Cassia obtusifolia), jimsonweed (Datura stramonium), velvetleaf (Abutilon theophrasti), lambsquarters (Chenopodium album), rice (Oryza sativa), and teaweed (Sida spinosa). The second pot is planted with green foxtail (Setaria viridis), cocklebur (Xanthium pensylvanicum), morningglory (Ipomoea hederacea), cotton (Gossypium hirsutum), johnsongrass (Sorghum halepense), barnyardgrass (Echinochloa crus-galli), corn (Zea mays), soybean (Glycine max), and giant foxtail (Setaria faberi). The third pot is planted with wheat (Triticum aestivum), barley (Hordeum vulgare), wild buckwheat (Polygonum convolvulus), downy brome (Bromus tectorum), sugarbeet (Beta vulgaris), wild oat (Avena fatua), common chickweed (Stellaria media), blackgrass (Alopecurus myosuroides), and rape (Brassica napus). The plants are grown for approximately fourteen days, then sprayed postemergence with the chemicals dissolved in a non-phytotoxic solvent. 
     Preemergence 
     Three round pans (25 cm diameter by 12.5 cm deep) are filled with Sassafras sandy loam soil. One pan is planted with nutsedge tubers, crabgrass, sicklepod, jimsonweed, velvetleaf, lambsquarters, rice, and teaweed. The second pot is planted with green foxtail, cocklebur, morningglory, cotton, johnsongrass, barnyardgrass, corn, soybean, and giant foxtail. The third pot is planted with wheat, barley, wild buckwheat, downy brome, sugarbeet, wild oat, common chickweed, blackgrass, and rape. The three pans are sprayed preemergence with the chemicals dissolved in a non-phytotoxic solvent. 
     Treated plants and controls are maintained in the greenhouse for approximately 24 days, then all rated plants are compared to controls and visually rated for plant response. 
     Response ratings used in Test B are used in some tests. In other tests the ratings are based on a scale of 0 to 100 where 0 indicates no effect, 20 minimal injury and 100 indicated complete control. A dash (--) response means no test is conducted. The results are shown in Table Ca-Cg. 
     
                       TABLE Ca______________________________________     Compound 1     250    62     16       4     Preemergence     g/ha______________________________________Spring wheat       10G      10G    2G     0Sugarbeet   10G      10G    10G    5GWild oats   10G       9G    0      0Corn         7G       4G    0      0Soybean     10G       7G    3G     0Cotton      10G       9G    4G     3GVelvetleaf  10G      10G    10G    5GMorningglory       10G      10G    5G     3GCrabgrass   10G      10G    3G     0Barnyardgrass       10G      10G    5G     0______________________________________ 
    
     
                       TABLE Cb______________________________________     Compound 1     250    62     16       4     Postemergence    g/ha______________________________________Spring wheat        9G      4G     0      0Sugarbeet   10G      10G     7G    0Wild oats   10G      8G     0      0Corn         8G      3G     0      0Soybean     10G      10G     9G    7GCotton      10G      10G    10G    9GVelvetleaf  10G      10G    10G    3GMorningglory       10G      10G    10G    4GCrabgrass    6G      2G     0      0Giant foxtail       --       6G     0      0Barnyardgrass       10G      4G     0      0______________________________________ 
    
     
                       TABLE Cc______________________________________   Compound 1   250  62     16      250  62   16   Preemergence               Postemergence g/ha______________________________________Spring wheat      90     20     0    100   60   0Sugarbeet 100    100    100   100  100  100Rape      100    100    100   100  100  100Wild oats 100     90     30   100  100  20Blackgrass     100    100     40   100   80  30Corn      100     70     40   100   70  30Soybean   100    100     40   100  100  60Cotton    100    100     60   100  100  100Velvetleaf     100    100    100   100  100  100Morningglory     100    100     90   100  100  100Crabggrass     100    100     90   100   70  40Giant foxtail     100    100    --    100  100  50Barnyardgrass     100    100     70   100  100  50Johnson grass     100    100    100   100  100  60Nutsedge  100     60     20   100   70  30Cocklebur 100    100    100   100  100  70Teaweed   100    100    100   100  100  100Cassia    100    100    100   100  100  100Johnsonweed     100    100    100   100  100  100Rice      100    100    100   100  100  100______________________________________ 
    
     
                       TABLE Cd______________________________________      Compound 2      250    62     16       4      Preemergence      g/ha______________________________________Spring wheat 100       50     0      0Winter barley         70       40     0      0Sugrarbeet   100      100    100    70Rape         100      100    90     70Wild oats    100      100    50     30Blackgrass    80       50     0      0Downy brome   30       0      0      0Lambsquarters        100      100    100    100Wild buckwheat        100      100    100    90Chickweed     60       30     0      0Corn          90       60    30      0Soybean      100       90    70      0Cotton       100       80    40     30Velvetleaf   100      100    100    70Morningglory 100      100    80     30Crabgrass    100      100    90     60Giant foxtail        100      100    100    30Barnyardgrass        100       90    60     30Johnson grass        100      100    80     30Nutsedge     100      100    50     30Green foxtail        100      100    100    30Cocklebur     90       80    60     20Teaweed      100      100    100    90Cassia       100      100    100    30Jimsonweed   100      100    100    60Rice         100       90    70     30______________________________________ 
    
     
                       TABLE Ce______________________________________      Compound 2      250    62     16       4      Postemergence     g/ha______________________________________Spring wheat 100       70    20      0Winter barley         80       30     0      0Sugarbeet    100      100    90     40Rape         100      100    100    90Wild oats    100       80    30      0Blackgrass   100       70    20      0Downy brome   90       30     0      0Lambsquarters        100      100    100    100Wild buckwheat        100      100    100    100Chickweed    100      100    40     10Corn          30       10     0      0Soybean      100      100    90     60Cotton       100      100    100    100Velvetleaf   100      100    100    80Morningglory 100      100    50     --Crabgrass    100       50    30     20Giant foxtail        100      100    20      0Barnyardgrass        100      100    50     10Johnson grass        100      100    40     20Nutsedge     100       90    40     --Green foxtail        100      100    30     20Cocklebur    100       40    40     30Teaweed      100      100    100    50Cassia        90       50    50     20Jimsonweed   100      100    100    80Rice         100      100    70     30______________________________________ 
    
     
                       TABLE Cf______________________________________      Compound 4      500    250    62       16      Preemergence      g/ha______________________________________Spring wheat  30      20     10      0Winter barley         30      20     20     10Sugarbeet    100      100    90     80Rape         100      100    40     30Wild oats     30      20      0      0Blackgrass    90      90     40     20Downy brome   20       0      0      0Lambsquarters        100      100    100    50Wild buckwheat        100      100    100    50Chickweed     0        0      0      0Corn          90      90     50     40Soybean       60      40     20      0Cotton        70      50     20      0Velvetleaf   100      100    90     30Morningglory  90      90     50     30Crabgrass    100      90     85     50Giant foxtail        100      100    90     30Barnyardgrass        100      100    90     30Johnson grass        100      100    40     20Nutsedge      60      20      0     --Green foxtail        100      100    90     50Cocklebur     50      30      0      0Teaweed      100      100    100    30Cassia        70      40     20     20Jimsonweed   100      100    50     30Rice         100      90     70     30______________________________________ 
    
     
                       TABLE Cg______________________________________       Compound 4       500  250       62       Postemergence g/ha______________________________________Spring wheat  10      0         0Winter barley  0      0         0Sugarbeet     100    60        10Rape          100    90        50Wild oats     20      0         0Blackgrass    50      0         0Downy brome    0      0         0Lambsquarters 100    100       80Wild buckwheat         100    100       100Chickweed     --     70        --Corn          10      0         0Soybean       80     80        70Cotton        80     60        50Velvetleaf    100    100       100Morningglory  60     30        30Crabgrass     70     60        30Giant foxtail --     70        30Barnyardgrass 90     40         0Johnson grass 100    30        10Nutsedge      70     40        10Green foxtail 100    80        20Cocklebur     60     30        20Teaweed       100    100       90Cassia        50     50        30Jimsonweed    100    90        80Rice          20     20        10______________________________________ 
    
     TEST D 
     Seeds of spring wheat (Triticum aestivum), winter wheat (T. aestivum), spring barley (Hordeum vulgare), winter barley (H. vulgare), sugarbeet (Beta vulgaris), rape (Brassica napus), wild oat (Avena fatua), downy brome (Bromus tectorium), cheatgrass (B. secalinus), blackgrass (Alopercurus myosuroides), annual bluegrass (Poa annum), green foxtail (Setaria viridis), Italian ryegrass (Lolium multiflorum), jointed goatgrass (Aegilops cylindrica), Matricaria indora, Galium spp., Russian thistle (Salsola kali), lambsquarters (Chenopodium album), kochia (Kochia scoparia), black nightshade (Solanum nigrum), speedwell (Veronica persica), wild buckwheat (Polygonium convolvulus), viola (Viola spp.), Veronica hederaefolia and field pennycress (Thlapsi arvensis) are placed in 26 cm plastic pans containing pasteurized sandy loam soil. Plantings are maintained in the greenhouse for 28 days at which time the postemergence treatments are applied using compounds formulated in a non-phytotoxic solvent. The preemergence portion of the test is seeded just before spraying. The postemergence treatments also contained wild oats and blackgrass at 1-leaf and 3-leaf growth stages. All treatments are held in the greenhouse for an additional 21 days at which time visual assessments of plant injury are made using a scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal injury and 100 indicates complete control. The results are shown in Tables Da and Db. 
     
                       TABLE Da______________________________________      Compound 1      64    32      16      8      Preemergence      g/ha______________________________________Spring wheat 100      80     50    20Winter wheat  90      80     50    10Spring barley         70      40     20    10Winter barley         70      50     20    20Sugarbeet    100     100     100   100Rape         100     100     100   70Wild oats     80      70     60    40Downy brome   90      70     40    20Cheatgrass    70      70     50    10Blackgrass    70      70     60    20Annual bluegrass         40      40     30    10Green foxtail        100     100     100   80Italian ryegrass         90      90     70    40Goatgrass     30      30     20     0Matricaria indora        100     100     100   100Galium        30      0       0     0Russian thistle        100     100     100   100Lambsquarters        100     100     100   100Kochia       100     100     100   70Black nightshade        100     100     100   100Speedwell    100     100     100   100Veronica hederaefolia        100     100     70    60Wild buckwheat        100     100     100   100Viola         80      70     50    20Field pennycress        100     100     100   100______________________________________ 
    
     
                       TABLE Db______________________________________      Compound 1      64    32      16      8      Postemergence     g/ha______________________________________Spring wheat  50     50      30    20Winter wheat  50     30      30    10Spring barley        100     30      20    20Winter barley         40     40      30    20Sugarbeet    100     90      90    80Rape         100     100     80    60Wild oats1-leaf       100     60      30    203-leaf        60     50      30    10Downy brome   40     10      10    10Cheatgrass    60     30      20     0Blackgrass1-leaf        70     20      20    103-leaf        30     20      20    10Annual bluegrass         20     20      10    10Green foxtail        100     100     70    60Italian ryegrass         90     60      20    10Goatgrass     30     20      20    10Matricaria indora        100     100     60    30Galium        70     40      40    20Russian thistle        100     100     100   100Lambsquarters        100     60      60    50Kochia       100     100     70    60Black nightshade        100     100     100   80Speedwell    100     80      80    60Veronica hederaefolia        100     100     100   100Wild buckwheat        100     100     100   100Viola         60     40      40     0Field pennycress        100     100     50    40______________________________________ 
    
     TEST E 
     Seeds of downy brome (Bromus tectorum), kochia (Kochia scoparia), optionally Russian thistle (Salsola kali), wild oats (Avena fatua), field bindweed (convolvulus arvensis), rye (Secale cereale), green foxtail (Setaria viridis) and winter wheat (Triticum aestivum) are placed in 26-cm plastic pans containing a pasteurized sandy loam soil (pH 6.5, 1% organic matter). Plantings are maintained in the greenhouse for 28 days at which time the postemergence treatments are applied using a nonphytotoxic solvent as the carrier for the herbicide. The preemergence segment of the test is seeded immediately before herbicide application using seeds of downy brome (Bromus tectorum), kochia (Kochia scoparia), optionally Russian thistle (Salsola kali), wild oats (Avena factua), field bindweed (Convolvulus arvensis), rye (Secale cereale), green foxtail (Setaria viridis), jointed goatgrass (Aegilops cyclindrica), wild buckwheat (Polygonium convolvus), pigweed (Amaranthus retroflexus) and lambsquarters (Chenopodium album). A separate pot is prepared using a sandy loam soil which contained the crop species barley (Hordeum vulgare), winter wheat (Triticum aestivum), spring wheat (Triticum aestivum), sorghum (Sorghum bicolor) and corn (Zea mays). 
     All treatments are maintained in the greenhouse for an additional 21 days at which time visual assessments of weed control are made using a scale of 0 to 100 for each species where 0 represents no control and 100 represents complete control. The results are shown in Tables Ea-Ec. 
     
                       TABLE Ea______________________________________   Compound 1   1000 250     125    64   32    g/ha______________________________________PostemergenceRussian thistle     100    100     100  100  100Kochia    100    100     100  100  100Downy Brome      90     90      90  80   30Green foxtail     100    100     100  100  100Wild oat  100    100     100  90   90Wheat     100     90      90  80   50Rye        90     80      70  70   20Field bindweed     100    100     100  100  100PreemergenceWheat     100    100      90  90   20Barley    100     90      80  60   20Corn      100     90      90  90    0Sorghum   100    100     100  100   0______________________________________ 
    
     
                       TABLE Eb______________________________________   Compound 1   1000 250     125    64   32    g/ha______________________________________PostemergenceRussian thistle     100    100     100  100  100Kochia    100    100     100  100  100Downy Brome     100     90      80   70  30Green foxtail     100    100     100  100  100Wild oat  100    100     100  100  80Wheat     100     90      90   90  60Rye       100    100     100  100  90Field bindweed     100    100     100  100  100PreemergenceWheat     100     90      80   80  70Barley    100     80      80   70  40Corn       80     80      70   50  50Sorghum   100    100      90   80  70______________________________________ 
    
     
                       TABLE Ec______________________________________      Compound 1      250   125      64     32   g/ha______________________________________PostemergenceRussian thistle        100     100      95   95Kochia       100     100      100  100Downy Brome   95      70      50   30Green foxtail        100     100      100  75Wild oat     100      95      70   50Wheat        100      80      50   45Rye           60      50      40   40Field bindweed        100     100      100  100PreemergenceWheat        100     100      70   30Barley       100      70      40   20Corn          98      90      80   70Sorghum      100     100      80   70Winter wheat  90      90      70   40Russian thistle        100     100      100  95Kochia       100     100      100  100Downy brome   98      75      60   30Green foxtail        100     100      100  100Wild oats    100      95      75   70Rye           40      40      40   30Field bindweed        100     100      100  100Jointed goatgrass         75      40      45   30Wild buckwheat        100     100      100  100Lambsquarters        100     100      100  100Pigweed      100     100      100  95______________________________________ 
    
     TEST F 
     The Corn and Sorghum Herbicide Test included the following species in both the preemergence and postemergence evaluations: 
     
         ______________________________________   SPECIESCategory  Common Name  Scientific Name______________________________________Crops     Corn         Zea mays     Soybean      Glycine max     Sorghum      Sorghum bicolorGrasses   Green foxtail                  Setaria viridis     Giant foxtail                  Setaria faberii     Johnsongrass Sorghum halepense     Barnyardgrass                  Echinochloa crus-galli     Fall panicum Panicum dichotomiflorum     Crabgrass    Digitaria sanguinalis     Nutsedge     Cyperus rotundusBroadleaves     Cocklebur    Xanthium pensylvanicum     Morningglory Ipomoea hederacea     Velvetleaf   Abutilon theophrasti     Jimsonweed   Datura stramonium     Lambsquarters                  Chenopodium album     Pigweed      Amaranthus retroflexus     Smartweed    Polygonum persicaris______________________________________ 
    
     Postemergence 
     Postemergence plantings are grown in Sassafras sandy loam soil. Corn and soybeans are grown in separate 25 cm diameter containers. Sorghum and the seven grass weed species are grown in two 18 cm diameter containers, 4 species per container. The seven broadleaf weed species are also grown in two 18 cm diameter containers, 4  species in one container, 3 species in the second container. One additional planting of corn in an 18 cm diameter container is made. The soil surface of this additional container of corn is covered with the absorbent, perlite, before spray treatment so that test chemicals would enter the plant only via the foliage. The plants are grown 10-21 days, dependent upon the species and then sprayed postemergence with the test chemicals dissolved in a non-phytotoxic solvent. 
     Preemergence 
     Preemergence plantings are grown in fertilized Tama silt loam soil. These plantings are identical to those described in the postemergence section, with the exception of the corn planting having perlite covering the soil surface. These plantings are made the day of or the day before spraying the test chemicals dissolved in a non-phytotoxic solvent. 
     Treated plants and controls are maintained in the greenhouse for 2 to 4 weeks. Visual ratings are made using a scale of 0 to 100 where 0 indicates no effect, and 100 indicates complete control. The results are shown in Table F. 
     
                       TABLE F______________________________________   Compound 1   250  125    64      32   16   8   Postemergence         g/ha______________________________________Corn       95     85     55   45   35    0Sorghum   100    100    100   85   75   40Soybean   100    100    100   90   75   50Green foxtail     100    100     95   80   65   35Giant foxtail     100    100     95   80   60   30Fall panicum     100    100    100   95   65   20Crabgrass  95     85     60   35    0    0Barnyardgrass     100     85     65   35   20    0Johnson grass     100    100     95   85   60    0Nutsedge  100     95     85   65   35    0Velvetleaf     100    100    100   100  100  100Cocklebur 100    100    100   100  60   20Smartweed 100    100    100   95   60   40Lambsquarters     100    100     95   90   80   50Pigweed   100    100     85   75   40   30IvyleafMorningglory     100    100    100   100  100  65Jimsonweed     100    100    100   100  95   45______________________________________ 
    
     TEST G 
     Stem cuttings of Mikania spp, lantana (Lantana camara) and Nephrolepis cordata are planted in separate 15.2 cm plastic pots filled with greenhouse planting medium. The plants are grown in the greenhouse until used. 
     The vigorously growing plants are sprayed postemergence with Compound 1 in a nonphytotoxic solvent. The treated plants are visually rated 45 DAT and compared with appropriate controls. The injury ratings are based on the scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. The results are shown in Table G. 
     
                       TABLE G______________________________________  Rate  g/ha   Lantana  Mikania spp.                             N. cordata______________________________________Compound 1    1000     50       75       60    500      0        55       40    250      0        30       20______________________________________ 
    
     TEST H 
     Large fiberglass tubs are filled with planting medium and planted with Rough lemon (Citrus sp.) rooted cutting, apple (Malus sp.) seedlings, grape (Vitis sp.) seedlings and pineapple (Ananas comosus) suckers are planted in one tube. A second tub is seeded with swollen fingergrass (Chloris inflata), guineagrass (Panicum maximum), goosegrass (Eleusine indica), itchgrass (Rottboellia cochinchinensis, Johnson grass (Sorghum halapense), large crabgrass (Digitaria sanguinalis), black nightshade (Solanum nigrum), pigweed (Amaranthus spp.), lambsquarters (Chenopodium spp), morningglory (Ipomoea sp.), common ragweed (Ambrosia elatior) and spanish needles (Bidens pilosa) seeds. The rough lemon, apple and grape plants are sprayed to simulate field type treatments where the spray covers only the trunk of the plant, the pineapple is sprayed postemergence and the weeds are treated preemergence. The tubs are treated with Compound 1 formulated in a non-phytotoxic solvent. Plants are visually rated 33 DAT and compared with appropriate controls. The injury rating scale used in Test G is also used. The results are shown in Table H. 
     
                       TABLE H______________________________________      Compound 1      500   250     125     64    g/ha______________________________________PostemergencePineapple     80      60      30    0PreemergenceRough lemon   0       0       0     0Apple         25      15      20    0Grapes       100     100      65   100Swollen fingergrass        100     100     100   100Guineagrass  100     100     100   100Goosegrass   100     100     100   100Itchgrass    100     100      90    50Johnson grass        100     100     100    90Large crabgrass        100     100     100   100Black nightshade        100     100     100   100Pigweed      100     100     100   100Lambsquarters        100     100     100   100Morningglory 100     100     100    80Ragweed      100     100     100   100Spanish needles        100      80      20    0______________________________________ 
    
     TEST I 
     Loblolly pine (Pinus taeda), swamp chestnut oak (Ouercus michauxii) and red cedar are planted in a 30-liter plastic pot. Rooted raspberry (Rubrus spp.) cuttings are also planted in another 30 -liter plastic pot filled with planting medium. The plants are grown in the greenhouse for over three months before being sprayed. 
     Plants are sprayed postemergence with Compound 1 formulated in a non-phytotoxic solvent. The treated plants are visually rated 31 DAT and compared with appropriate controls. Plant injury scale used in Test G is used in this test also. The results are shown in Table I. 
     
                       TABLE I______________________________________      Plant Injury Rating  Rate  Loblolly Swamp      Red   Rasp-  g/ha  pine     Chestnut Oak                            Cedar berry______________________________________Compound 1    1000    0        80       0     30    500     0        80       0     20    250     0        80       0     10    125     0        80       0      0     64     0        80       0      0______________________________________ 
    
     TEST J 
     Rooted cuttings of rough lemon (Citrus sp.) are planted in 30-liter plastic pots. These pots are also seeded with guineagrass (Panicum maximum), pigweed (Amaranthus spp.), narrowleaf panicum (P. maximum), Texas panicum (P. texanum) seeds and yellow nutsedge tubers. Two 20.3 cm pots are filled with planting medium. One is planted with apple (Malus spp.) seedling and seeded with Johnsongrass (Sorghum halapense), blackgrass (Alopecurus myosuroides) seeds and Paspalum conjugatum node cuttings. The second pot is planted with grape (Vitis spp.) seedlings and seeded with wild radish (Raphanus raphanistrum). 
     The citrus and grapes are sprayed to simulate field type post-directed herbicide application while the grapes and weeds are treated postemergence with Compound 1 formulated in a non-phytotoxic spray solvent. Plants are visually rated 36 DAT and compared with the appropriate controls. The injury rating scale used in Table G is also used. The results are shown in Table J. 
     
                       TABLE J______________________________________      Compound 1      1000 500     250    125  64    g/ha______________________________________Post-directedRough lemon   0      0       0   0    0Apple         0      0       0   0    0PostemergenceGrapes        0*     0*      0*   0*  --Guineagrass  100    80      70   70   0Yellow nutsedge        100    80      60   0    0Pigweed      90     90      80   0    0Narrowleaf panicum        90     70      60   0    0Texas panicum        100    100     100  60   60Paspalum conjugatum        40     20       0   0    0Johnson grass        70     70      70   30   0Wild radish  90     50      30   30   --Blackgrass   90     20       0   0    --______________________________________ *initial burn but plant recovered. 
    
     TEST K 
     Coffee (Coffea spp.), Mikania spp. cuttings and thistle rhizomes are planted in separate 15.2 cm pots filled with planting medium. 19-liter pots filled with planting medium are planted with Eucalyptus spp. The plants are grown in the greenhouse until used. 
     Plants are treated postemergence with Compound 1, formulated in a non-phytotoxic solvent. One coffee plant is treated post-directed to simulate field treatment. Plants are visually rated 29 DAT and compared with the appropriate controls. Plant injury rating scale used in Test G is used in this test also. The results are shown in Table K. 
     
                       TABLE K______________________________________     Compound 1     1000   500    250      125  g/ha______________________________________Post-directedCoffee      10       10      5     --PostemergenceCoffee       40*      40*    40*   --Eucalyptus  70       60     50     --Mikania     90       80     70     60Thistle     20       20     20     10______________________________________ *initial burn 
    
     TEST L 
     Banana (Musa sp.) plants growing in 20.3 cm pots were used in this test. Plants at the 11-leaf stage were sprayed with Compound 1 in a non-phytotoxic solvent. The treatments were applied over-the-top in one group of plants and post-directed to simulate field-type treatment in another group. Treated plants were visually rated 54 DAT and compared with the appropriate controls. Plant injury rating scale used in Test G is used in this test also. The results are shown in Table L. 
     
                       TABLE L______________________________________      Compound 1      250 g/ha      Over-the-Top               Post-directed______________________________________Banana       0          0______________________________________ 
    
     TEST M 
     In a field trial, plots with first year citrus (gragefruit and orange) trees were used. The plots also had the weeds crabgrass (Digitaria spp.), Florida pusley (Richardia scabra), and prostrate spurge (Euphorbia supina) at the mature and blooming stage of growth. Plots were sprayed with Compound 1 in a non-phytotoxic solvent. Treatments were applied post-directed to the citrus and postemergence to the weeds. Plants were visually rated 112 DAT and compared with the controls using the 0 to 100 injury rating scale, where 0=no effect and 100=complete control. The results are shown in Table M. 
     
                       TABLE M______________________________________       Compound 1       64   32       16    ounces/acre______________________________________Citrus         0      0        0Crabgrass      98    98       85Florida pusley         100    97       85Prostrate spurge         100    100      97______________________________________