HERBICIDES FOR CITRUS, SUGARCANE, OIL PALM AND THE LIKE

Abstract: The invention is directed to use of herbicides of Formula (I), and its agriculturally suitable salts, wherein R is isopropyl, allyl, propargyl or -CH(CH3)C=CH; X is Cl or Br; Y is F or Cl; Z is H or can be taken together with R as (a) such that the linking oxygen is attached to the methine carbon. Herbicides that comprise compounds of formula (I) provide broad spectrum weed control in citrus, sugarcane, coffee, banana, oil palm, loblolly pine, rubber, cocoa, grapes, plantain, pineapple, fruit trees such as apple trees, nut trees, and turf grass such as Kentucky bluegrass and the like.

Description: TITLE HERBICIDES FOR CITRUS, SUGARCANE, OIL PALM AND THE LIKE CROSS-REFERENCE TO RELATED APPLICATION This application is a continuation-in-part of application U.S. Serial No. 07/649,355, filed February 1, 1991. 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. Patent 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 wherein R is isopropyl, allyl, propargyl or -CH(CH3>C«CH; X is Cl or Br; Y is F or Cl; Z is H or can be taken together with R as I -CH2CHCH3 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-propynyl)oxy]~ phenyl]tetrahydro-lH-[1,2,4]-triazolo[1,2-a]pyridazine- 1,3(2H)-dione or 2-(7-chloro-5-f * *>ro-2,3-dihydro-2- methyl-4-benzofuranyl)tetrahydro- d-[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. 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: £ £ 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. Patent 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, "Agglomeration", Chemical Engineering. December 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 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. Patent 3,235,361, February 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41; R. W. Luckenbaugh, U.S. Patent 3,309,192, Marchl4, 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. Patent 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and J. D. Fryer and S. A. Evans, "Weed Control Handbook", 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* Diluen ( a, Surfactan (s) 0-74 1-10 40-95 0-15 *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., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, New Jersey, 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 ormulations. Typical liquid diluents and solvents that may be included in the formulations are described in Marsden, "Solvents Guide", 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 β C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", 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 Wettable Powder 2-[4-chloro-2-fluoro-5-[ (2-propynyl)oxy]phenyl]- tetrahydro-lH-[1,2,4]-triazolo[1,2-a]pyridazine- 1,3(2H)-dione 80% sodium 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 Wettable Powder 2-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]- tetrahydro-lH-[1,2,4]-triazolo[1,2-a]pyridazine- l,3(2H)-dione 50% sodium 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 Granule 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 Extruded Pellet 2-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]- tetrahydro-lH-[1,2,4]-triazolo[1,2-a]pyridazine- l,3(2H)-dione 25% anhydrous 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 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 Low Strength Granule 2-[4-chloro-2-fluoro-5-[ (2-propynyl)oxy]phenyl]- tetrahydro-lH-[1,2,4]-triazolo[l,2-a]pyridazine- l,3(2H)-dione 1% N,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 Granule 2-[4-chloro-2-fluoro-5-[ (2-propynyl)oxy]phenyl]- tetrahydro-lH-[1,2,4]-triazolo[1,2-a]pyridazine- l,3(2H)-dione 80% wetting 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 Aqueous Suspension 2-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl3- tetrahydro-lH-[1,2,4]-triazolo[1,2-a]pyridazine- l,3(2H)-dione 40% polyacrylic 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 High Strength Concentrate 2-[4-chloro-2-fluoro-5-[(2-propynyl)oxyjphenyl]- tetrahydro-lH-[1,2,4]-triazolo[1,2-a]pyridazine- l,3(2H)-dione 99% silica 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 Wettable Powder 2-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]- tetrahydro-lH-[1,2, ]-triazolo[1,2-a]pyridazine- l,3(2H)-dione 90% dioctyl 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 Wettable Powder 2-[4-chloro-2-fluoro-5-[ (2-propynyl)oxy]phenyl]- tetrahydro-lH-[1,2,4]-triazolo[1,2-a]pyridazine- l,3(2H)-dione 40% sodium 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 Oil Suspension 2-[4-chloro-2-fluoro-5-[ (2-propynyl)oxy]phenyl]- tetrahydro-lH-[1,2,4]-triazolo[1,2-a]pyridazine- l,3(2H)-dione 35% blend of polyalcohol carboxylic esters 6% and oil soluble petroleum sulfonates xylene 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 Dus 2-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenylJ- tetrahydro-lH-[1,2,4]-triazolo[1,2-a]pyridazine- l,3(2H)-dione 10% attapulgite 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 Oil Suspension 2-[4-chloro-2-fluoro-5-[(2-proρynyl)oxy]phenyl]- tetrahydro-lH-[1,2,4]-triazolo[1,2-a]pyridazine- l,3(2H)-dione 25% polyoxyethylene 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)acetamide acifluorfen 5-[2-chloro-4-(trifluoromethyl)- phenoxy]-2-nitrobenzoic acid acrolein 2-propenal alachlor 2-chloro-N-(2,6-diethylphenyl)-N- (methoxymethyl)acetamide anilofos S-4-chloro-N-isopropylcarbaniloyl- methyl-O,O-dimethyl phosphorodi- thioate carbamate atrazine 6-chloro-N-ethyl-N'-(1-methylethyl)- 1,3,5-triazine-2,4-diamine barban 4-chloro-2-butynyl 3-chlorocarbamate benefin N-butyl-N-ethyl-2,6-dinitro-4-(tri- fluoromethyl)benzenamine bensulfuron 2-[[[[[( , -dimethoxy-2-pyrimi- methyl dinyl)aminojmethylcarbonyl]- amino]sulfonyl]methyl]benzoic acid, methyl ester bensulide 0,0-bis(1-methylethyl) S-[2- [(phenylsulfonyl)amino]- ethyl]phosphorodithioate bentazon 3-(1-methylethyl)-(1H)-2,1,3- benzothiadiazin-4(3H)-one, 2,2-dioxide benzofluor N-[4-(ethylthio)-2-(trifluoro¬ methyl)phenyl]methanesulfonamide benzoylprop N-benzoyl-N-(3,4-dichlorophenyl)-DL- alanine bifenox methyl 5-(2,4-dichlorophenox )-2- nitrobenzoate bromacil 5-bromo-6-meth l-3-(1-methylpropyl)- 2,4(1H,3H)pyrimidinedione bromoxynil 3,5-dibromo-4-hydroxybenzonitrile Common Name Chemical Name butachlor N-(butoxymethyl)-2-chloro-N-(2,6- diethylpheny1)acetamide buthidazole 3-[5-(1,1-dimethylethyl)-1,3,4-thia- diazol-2-yl]-4-hydroxy-l-methyl-2- imidazolidinone butralin 4-(1,1-dimethylethyl)-N-(1-methyl- propyl)-2,6-dinitrobenzenamine butylate S-ethyl bis(2-methylpropyl)- carbamothioate cacodylic dimethyl arsinic oxide acid CDAA 2-chloro-N,N-di-2-propenylacetamide CDEC 2-chloroallyl diethyldithiocarbamate CGA 142,464 3-(4,6-dimethoxy-l,3,5-triazin-2-yl)- 1-[2-(2-methoxyethoxy)-pehnyl- sulfonyl]-urea chloramben 3-amino-2,5-dichlorobenzoic acid chlorbromuron 3-(4-bromo-3-chlorophenyl)-1-methoxy-l- methylurea chlorimuron 2-[[[[(4-chloro-6-methoxy-2-pyrimi- ethyl dinyl)ethylamino]carbonyl]- amino]sulfonylJbenzoic acid, ethyl ester chlormethoxy- 2,4-dichlorophenyl 4-nitro-3- nil methoxyphenyl ether chlornitrofen 2,4,6-trichlorophenyl-4-nitro- phenyl ether chloroxuron N'-[4-(4-chloroρhenoxy)phenyl]-N,N- dimethylurea chlorpropham 1-methylethyl 3-chlorophenylcarbamate Common Name Chemical Name chlorsulfuron 2-chloro-N-[[(4-methoxy-6-methyl-l,3,5- triazin-2-yl)amino]carbonyl]benzene- sulfonamide chlortoluron N*-(3-chloro-4-methylphenyl)-N,N- dimethylurea cinmethylin exo-l-methyl-4-(1-methylethyl)-2-[(2- methylphenyl)methoxy]-7-oxabicyclo- [2.2.1]heptane clethodim (E,E)-(±)-2-[1-[[(3-chloro-2-propenyl)- oxy]i ino]propyl]-5-[2-(ethylthio)- propyl]-3-hydroxy-2-cyclohexen-l-one clomazone 2-[(2-chlorophenyl)methyl]-4, -dimethyl- 3-isoxazolidinone cloproxydim (E,E)-2-[l-[[ (3-chloro-2-propenyl)oxy)- imino]butyl]-5-[2-(ethylthio)propyl]- 3-hydroxy-2-cyclohexen-l-one clopyralid 3,6-dichloro-2-pyridinecarboxylic acid CMA calcium salt of MAA cyanazine 2-[[4-chloro-6-(ethylamino)-1,3,5-tri- azin-2-yl]amino]-2-methylpropanenitrile cycloate S-ethyl cyclohexylethylcarbamothioate cycluron 3-cyclooctyl-l,1-dimethylurea cyperquat l-methyl-4-phenylpyridinium cyprazine 2-chloro-4-(cyclopropylamino)-6-(iso- propylamino)-i-triazine cyprazole N-[5-(2-chloro-l,1-dimethylethyl)-1,3,4- thiadiazol-2-y1]cyclopropanecarbox- amide cypromid 3',4'-dichlorocyclopropanecarboxanilide dalapon 2,2-dichloropropanoic acid Common Name Chemical Name dazomet tetrahydro-3,5-dimethyl-2H-l,3,5-thia- diazine-2-thione DCPA dimethyl 2,3,5,6-tetrachloro-l,4-benzene- dicarboxylate desmediphan ethyl [3-[[ (phenylamino)carbonyl]oxy]- phenyl]carbamate desmetryn 2-(isopropylamino)-4-(methylamino)-6- (methylthio)-ja-triazine diallate S-(2,3-dichloro-2-propenyl)bis(1- methylethyl)carbamothioate dicamba 3,6-dichloro-2-methoxybenzoic acid dichlobenil 2,6-dichlorobenzonitrile dichlorprop (±)-2-(2,4-dichlorophenoxy)propanoic acid dichlofop (±)-2-[4-(2,4-dichlorophenoxy)phenoxy]- propanoic acid, methyl ester diethatyl N-(chloroacetyl)-N-(2,6-diethylphenyl)- glycine difenzoquat 1,2-dimethy1-3,5-diphenyl-lH-pyrazolium dimepiperate S-1-methyl-l-phenylethylpiperidine- 1-carbothioate dinitramine N 3 ,N 3 -diethyl-2,4-dinitro-6-(trifluoro¬ methyl)-1,3-benzenediamine dinoseb 2-(1-methylpropyl)-4,6-dinitrophenol diphenamid N,N-dimethyl-a-phenylbenzeneacetamide dipropetryn 6-(ethylthio)-N,N'-bis(1-methylethyl)- 1,3,5-triazine-2,4-diamine diqu t 6,7-dihydrodipyrido[1,2-a:2',1'-c]- pyrazinedium ion diuron '-(3,4-dichloropheny1)-N,N-dimethylurea 1-pheny ethy urea endothall 7-oxabicyclo[2.2.1]heptane-2,3-dicarbox- ylic acid EPTC S-ethyl dipropylcarbamothioate esprocarb S-benzyl-N-ethyl-N-(1,2-dimethyl)- propyl)thiolcarbamate ethalfluralin N-ethyl-N-(2-methyl-2-ρropenyl)-2,6- dinitro-4-(trifluoromethyl)- benzenamine ethofumesate (+)-2-ethoxy-2,3-dihydro-3,3-dimethyl- 5-benzofuranyl methanesulfonate Express* 2-[[[[N-(4-methoxy-6-methyl-l,3,5- triazine-2-yl)-N-methylamino]- carbonyl]amino]sulfonyl]benzoic acid, methyl ester fenac 2,3,6-trichlorobenzeneacetic acid fenoxaprop (±)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]- phenoxy]propanoic acid fenuron N,N-dimethy1-N'-phenylurea fenuron TCA Salt of fenuron and TCA flamprop N-benzoyl-N-(3-chloro-4-fluorophenyl)- DL-alanine fluazifop (+)-2-[4-[[5-(trifluoromethyl)-2-pyri- dinyl]oxy]phenoxy]propanoic acid fluazifop-P (R)-2-[4-[[5-(trifluoromethyl)-2-pyri- dinyl]oxy]phenoxy]propanoic acid fluchloralin N-(2-chloroethyl)-2,6-dinitro-N-propyl- 4-(trifluoromethyl)benzenamine Common Name Chemical Name fluometuron N,N-dimethyl-N'-[3-(trifluoromethyl)- phenyl]urea fluorochlor- 3-chloro-4-(chloromethyl)-1-[3-(tri- idone fluoromethyl)phenyl]-2-pyrrolidinone fluorodifen p-nitrophenyl a,a,a-trifluoro-2-nitro- p-tolyl ether fluorogly- carboxymethyl 5-[2-chloro-4-(tri- cofen fluoromethyl)phenoxy]-2-nitrobenzoate fluridone l-methyl-3-phenyl-5-[3-(trifluoro¬ methyl)phenyl]-4 (1H)-pyridinone fomesafen 5-[2-chloro-4-(trifluoromethyl)phenoxy]- N-(methylsulfonyl)-2-nitrobenzamide fosamine ethyl hydrogen (aminocarbonyl)- phosphate glyphosate N-(phosphonomethyl)glycine haloxyfop 2-[4-[[3-chloro-5-(trifluoromethyl)-2- pyridinyl]oxy]phenoxy]propanoic acid Harmony β 3-[[[[(4-methoxy-6-methyl-l,3,5-triazin- 2-yl)amino]carbonyl]amino]sulfonyl]- 2-thiophenecarboxylic acid, methyl ester hexaflurate potassium hexafluoroarsenate hexazinone 3-cyclohexyl-6-(dimethylamino)-1-methyl- l,3,5-triazine-2,4 (lH,3H)-dione imazametha- 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 ester imazapyr (±)-2-[4,5-dihydro-4-methyl-4-(1-methyl¬ ethyl)-5-oxo-lH-imidazol-2-yl]-3- pyridinecarboxylic acid (2-methylpropyl) -6- (trif luoromethyl) - 3, 5-pyridinedicarbothionate Common Name Chemical Name napropamide N,N-di thyl-2-(1-naphthalenyloxy)- propanamide naptalam 2-[ (1-naphthalenylamino)carbonyl]- be zoic acid neburon l-butyl-3-(3,4-dichlorophenyl)-1-methyl- urea nitralin 4-(methylsulfonyl)-2,6-dinitro-N,N- dipropylaniline nitrofen 2,4-dichloro-l-(4-nitrophenoxy)benzene nitrofluorfen 2-chloro-l-(4-nitrophenoxy)-4-(tri- luoromethyl)benzene norea N,N-dimethyl-N*-(octahydro-4,7-methano- lH-inden-5-yl)urea 3aa,- 4a,5a,7a,7aa-isomer norflurazon 4-chloro-5-(methylamino)-2-[3-(tri- fluoromethyl)phenyl]-3(2H)- pyridazinone oryzalin 4-(dipropylamino)-3,5-dinitro- benzenesulfonamide oxadiazon 3-[2,4-dichloro-5-(1-methylethoxy)- phenyl]-5-(1,1-dimethylethyl)- 1,3,4-oxadiazol-2(3H)-one oxyfluorfen 2-chloro-l-(3-ethoxy-4-nitrophenoxy)-4- (trifluoromethyl)benzene paraquat 1,1'-dimethy1-4,4'-dipyridinium ion pebulate S-propyl butylethylcarbamothioate pendimethalin N-(1-ethylpropyl)-3,4-dimethyl-2,6- dinitrobenzenamine perfluidone 1,1,1-trifluoro-N-[2-methyl-4-(phenyl- sulfonyl)phenyl]methanesulfonamide phenmedipham 3-[(methoxycarbonyl)amino]phenyl (3- methylphenyl)carbamate Common Name Chemical Name picloram 4-amino-3,5,6-trichloro-2-pyridine- carboxylic acid PPG-1013 5-[2-chloro-4-(trifluoromethyl)- phenoxy]-2-nitroacetophenone oxime-O-acetic acid, methyl ester pretilachlor α-chloro-2,6-diethyl-N-(2-propoxy- ethyl)acetanilide procyazine 2-[[4-chloro-6-(cyclopropylamino)-l,3,5- triazine-2-yl]amino]-2-methylpropane- nitrile profluralin N-(cyclopropylmethyl)-2,6-dinitro-N- propyl-4-(trifluoromethyl)benzenamine prometon 6-methoxy-N,N'-bis(1-methylethyl)-1,3,5- triazine-2,4-diamine prometryn N,N'-bis(1-methylethyl)-6-(methylthio)- 1,3,5-triazine-2,4-diamine pronamide 3,5-dichloro-N-(1,l-dimethyl-2-propyn- yl)benzamide propachlor 2-chloro-N-(1-methylethyl)-N- phenylacetamide propanil N-(3,4-dichloropheny1)propanamide propazine 6-chloro-N,N'-bis(1-methylethyl)- 1,3,5-triazine-2,4-diamine propham 1-methylethyl phenylcarbamate prosulfalin N-[[4-(dipropylamino)-3,5-dinitro- phenyl]sulfonyl]-S,S-dimethylsulfil- imine prynachlor 2-chloro-N-(l-methyl-2-propynyl)acet¬ anilide pyrazolate 4-(2,4-dichlorobenzoyl)-l,3-dimethyl- pyrazol-5-yl-p-toluenesulphonate Common Name Chemical Name pyrazon 5-amino-4-chloro-2-phenyl-3(2H)- pyridazinone pyrazosulfuron ethyl S-[3-(4,6-dimethoxypyrimidin-2- ethyl yl)ureadosulfonyl]-1-methylpyrazole- 4-carboxylate quinclorac 3,7-dichloro-8-quinoline carboxylic acid quizalofop (+)-2-[4-[(6-chloro-2-quinoxalinyl)- ethyl oxy]phenoxy]propanoic acid, ethyl ester secbumeton N-ethyl-6-methoxy-N'-(1-methylpropyl)- 1,3,5-triazine-2,4-diamine sethoxydim 2-[1-(ethoxyimino)butyl]-5-[2-(ethyl¬ thio)propyl]-3-hydroxy-2-cyclohexen- 1-one siduron N-(2-methylcyclohexyl)-N*-phenylurea simazine 6-chloro-N,N*-diethyl-1,3,5-triazine- 2,4-diamine SK-233 1-(a,a-dimethylbenzyl)-3-(4-methyl- phenyl)urea sulfometuron 2-[[[[(4,6-dimethyl-2-pyrimidinyl)- methyl amino]carbonyl]amino]sulfonyl]- benzoic acid, methyl ester TCA trichloroacetic acid tebuthiuron N-[5-(1,1-dimethylethyl)-1,3,4-thiadi- azol-2-yl]-N,N'-dimethylurea terbacil 5-chloro-3-(1,1-dimethylethyl)-6- methyl-2,4(1H,3H)-pyrimidinedione terbuchlor N-(butoxymethyl)-2-chloro-N-[2-(1,1- dimethylethyl)-6-methylphenyl]- acetamide terbuthyl- 2-(tsri-butylamino)-4-chloro-6-(ethyl- azine amino)-i-triazine Common Name Chemical Name terbutol 2,6-di-t f iχt-butyl-r2-tolyl methylcar- bamate terbutryn N-(1,1-dimethylethyl)- '-ethyl-6- (methylthio)-rl,3,5-triazine- 2,4-diamine thiobencarb S-[(4-chlorophenyl)methyl] diethylcar- bamothioate triallate S-(2,3,3-trichloro-2-propenyl) bis(1- methylethyl)carbamothioate triclopyr [ (3,5,6-trichloro-2-pyridinyl)- oxy]acetic acid tridiphane 2-(3,5-dichlorophenyl)-2-(2,2,2- trichloroethyl)oxirane trifluralin 2,6-dinitro-N,N-dipropyl-4-(tri- fluoromethyl)benzenamine trimeturon 1-(p-chlorophenyl)-2,3,3-trimethylpseu- dourea 2,4-D (2,4-dichlorophenoxy)acetic acid 2,4-DB 4-(2,4-dichlorophenoxy)butanoic acid vernolate S-propyl dipropylcarbamothioate xylachlor 2-chloro-N-(2,3-dimethylpheny1)-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 (-CH2OKCH), 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 I (-CH2CHCH3) such that the linking oxygen is attached to the methine carbine, Y is F, and X is Cl. Compound 2 has the following structure: Compound 4 means compounds of Formula I where R and Z I are taken together as (-CH2CHCH3) such that the linking oxygen is attached to the methine carbon, Y is Cl, and X is Cl. Compound 4 has the following structure: Plastic tray liners with individual planting compartments are filled with planting medium and seeded separately with bermudagrass fCynodon dactylon , broadleaf signalgrass Brachiaria pl typh la) , guineagrass (Panicum maximum) , smooth crabgrass (Digitaria ischae um) , barnyardgrass (Echinocloa crus- sjall±.) , large crabgrass (P.. sanyuinalisϊ , johnsongrass (Sorghum h i ensei , Texas panicum (Panicum texanu ), sandbur (Cenchrus echinatus) , itchgrass (Ror.t.boellia cochinchinensist, goosegrass (Eleusine indical, dallisgrass (Paspalum dilatatumi , annual bluegrass (Ea SLΩΣL-m) , alfalfa fMedicaςro sativa) t Pueraria javanica, morningglory (Ipo ea spp.), purslane (Portulaca oleracea) , field bindweed (Convolvulus arvensis) , ragweed (Ambrosia elatior), peanut (Arachis hypogea), purple nutsedge (Cyperus rotundus) , yellow nutsedge (£. esculeutus) , and Kentucky bluegrass sod (P_oa 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 g/ha TEST B Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloa crus-gallii, giant foxtail (Setaria faberi), wild oats (Azena. fatua), cheatgrass Qromus secalinusi, 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 g/ha g/ha g/ha 3£≤I_£ 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 ( igitaria sanguinalis), sicklepod (Cassia obtusifolia), jimsonweed fDatura stramonium) , velvetleaf (Abutilon theophrasti \, lambsquarters (Chenopodium .album), rice (Ω∑yza. sativai, and teaweed (≤ida spinosa) • The second pot is planted with green foxtail (βetaria viridis), cockiebur (Xanthium pensylvanicu ) , morningglory (ipomoea hederacea) , cotton (Gossypium hirsutum), johnsongrass (Sorghum halepense), barnyardgrass (Echinochloa crus-gallii, corn (Zsa. mays) , soybean (Glycine jaai), and giant foxtail (Setaria aberi) . The third pot is planted with wheat (Triticum aestivum), barley (Hordeum vulgare), wild buckwheat fPolygonum convolvulus) , downy brome fBromus tectorum) , sugarbeet {Be a vul arise , wild oat ( ϊsna fatua) , common chickweed (Stellaria media) , blackgrass (Alopecurus myosuroides) , and rape (Brassica jiapua) . The plants are grown for approximately fourteen days, then sprayed postemergence with the chemicals dissolved in a non- phytoxic 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, cockiebur, 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. 36 T&RT.E Ca g/ha TABLE CC Compound 1 g/ha g/ha 40 TABLE Ce site TABLE Cg Compound 4 g/ha Spring wheat Winter barley Sugarbeet Rape Wild oats Blackgrass Downy brome Lambsquarters Wild buckwheat Chickweed Corn Soybean Cotton Velvetleaf Morningglory Crabgrass Giant foxtail Barnyardgrass Johnson grass Nutsedge Green foxtail Cockiebur Teaweed Cassia Jimsonweed Rice Seeds of spring wheat fTriticum aestiYum) , winter wheat (I. aestivumi , spring barley (Hordeum vulgare) , winter barley (fl. vulgarei , sugarbeet (Beta vulgaris) , rape /Brassica aapilS.) , wild oat ( Avena fatua) , downy brome (Bro us tectorium) , cheatgrass (£. secalinus) , blackgrass (Alop rcurus myosuroides) , annual bluegrass (£Δ ajmuxα) , green foxtail (Setaria viridis) , Italian ryegrass (Lolium multifloriimϊ , jointed goatgrass (Aegilops cylindrica), Matricaria indora, Galium spp., Russian thistle {Salsola Jςa i) , lambsquarters fChenopodium album! , kochia fKochia sπnparja * , black nightshade (Solanum xά cum) , speedwell (Veronica persica^ , wild buckwheat Polygonium convolvulus^ , viola (.Yiώla spp.), Veronica hederaefolia and field pennycress (Thlapsi arvensist 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. TEST E Seeds of downy brome (Bro us tectomm) , kochia {Kochia scoparia), optionally Russian thistle (Salsola iali.), wild oats (Asεena .fatua), field bindweed (convolvulus arvensisi , rye (Secale cereale) , green foxtail CSetaria viridisi and winter wheat (Tri icum aestivTim) 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 (AX£&a. fa ua ) r field bindweed (Convolvulus arvensisi , rye tSecale cereale), green foxtail fSetar viridis'i, jointed goatgrass (Aegilops cyclindricaϊ, wild buckwheat (Polygonium eonvoivuai , pigweed (A aranthus retrofleκus) and lambsquarters (Chenopodium album) . A separate pot is prepared using a sandy loam soil which contained the crop species barley (Hordeum vulgarei , winter wheat fTriticum aestivum), spring wheat (Triticum aestivumi , sorghum (Sorghum bicolor) and corn (z&a. 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 _£! -2Z g/ha Postemergence Russian thistle Kochia Downy Brome Green foxtail Wild oat Wheat Rye Field bindweed Preemergence Wheat Barley Corn Sorghum TABLE Et? Compound 1 1000 250 125 -£A -2 ste Postemergence Russian thistle Kochia Downy Brome Green oxtail Wild oat Wheat Rye Field bindweed Preemergence Wheat Barley Corn Sorghum TABLE EC Compound 1 250 125 SA 22 S te. Postemergence Russian thistle Kochia Downy Brome Green foxtail Wild oat Wheat Rye Field bindweed Preemergence Wheat Barley Corn Sorghum Winter wheat Russian thistle Kochia Downy brome Green foxtail Wild oats Rye Field bindweed Jointed goatgrass Wild buckwheat Lambsquarters Pigweed TEST F The Corn and Sorghum Herbicide Test included the following species in both the preemergence and postemergence evaluations: SPECIES Category Common Name Scientific Name Crops Corn Zea mays Soybean Glycine max Sorghum Sorghum bicolor Grasses Green foxtail Setaria viridis Giant foxtail Setaria faberii Johnsongrass Sorghum halepense Barnyardgrass Echinochloa crus-galli Fall panicum Panicum dichotomiflorum Crabgrass Digit,aria sap jna is Nutsedge Cyperus rotundus Broadleaves Cockiebur Xanthium pensylvanicum Morningglory Ipomoea hederacea Velvetleaf Abutilon theophrasti Jimsonweed Datura stramonium Lambsquarters Chenopodium album Pigweed A aranthus retroflexus Smartweed Polygonu 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 thegreenbouse 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 1 250 225 -SA - _ 1£ g/ha Postemergence TEST G Stem cuttings of Mikania spp, lantana fLantana 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. TEST H Large fiberglass tubs are filled with planting medium and planted with Rough lemon (Citrus sp.) rooted cutting, apple .Malus sp.) seedlings, grape ( i is sp. ) seedlings and pineapple (Ananas comosusϊ suckers are planted in one tube. A second tub is seeded with swollen fingergrass fChloris inflata), guineagrass (Panicum maximum), goosegrass (Eleusine indica) , itchgrass (Rottboellia cochinchinensis r Johnson grass (Sorghum halapense), large crabgrass igitaria sanguinalis) , black nightshade (Solanum nigrumi, 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. 2&&LE-H Compound 1 Postemergence Pineapple 80 60 30 Preemergence Rough lemon Apple Grapes Swollen fingergrass Guineagrass Goosegrass Itchgrass Johnson grass Large crabgrass Black nightshade Pigweed Lambsquarters Morningglory Ragweed Spanish needles TEST T 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 g/ha Compound 1 1000 500 250 125 64 TEST J Rooted cuttings of rough lemon (Citrus sp.) are planted in 30-liter plastic pots. These pots are also seeded with guineagrass fPanicum maximum) , pigweed (Amaran hus spp. r narrowleaf panicum (£. maximum) . Texas panicum (£. texanum) seeds and yellow nutsedge tubers. Two 20.3cm pots are filled with planting medium. One is planted with apple fMalus spp.) seedling and seeded with Johnsongrass (Sorghum halapensei, blackgrass (Alopecurus myosuroiries) seeds and Paspalum conjugatum node cuttings. The second pot is planted with grape (Vitis .spp.) seedlings and seeded with wild radish (Raph nus 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. * — initial burn but plant recovered. TEST K Coffee fCoffea 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 ucalyp us spp. The plants are grown in the greenhouse until used. Plants are treated postemergence with Compoundl, 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-directed Coffee 10 10 Postemergence Coffee Eucalyptus Mikania Thistle * - initial burn TEST L Banana fMusa 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 25Q g/ha Qver-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 acabrai , 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.

Claims: CLAIMS What is claimed is: 1. A method for controlling undesired weeds in crops selected from the group of citrus, sugarcane, coffee, banana, oil palm, loblolly pine, rubber, cocoa, grapes, plantain, pineapple, fruit trees such as apples, nut trees, and turf grass which comprises applying to the locus of the weeds a herbicidally effective amount of a compound of Formula I wherein R is isopropyl, allyl, propargyl or -CH(CH3)CBCH; X is Cl or Br; Y is F or Cl; and Z is H or can be taken together with R as I -CH2CHCH3 such that the linking oxygen is attached to the methine carbon. 2. The method of Claim 1 wherein X is Cl, Y is F, and Z is H. 3. The method of Claim 2 wherein the crop is selected from the group of citrus, sugarcane, coffee, banana, oil palm and loblolly pine. 4. The method of Claim 2 wherein the compound is 2-[4-chloro-2-fluoro-5-[ (2-propynyl)oxy]phenyl]tetra- hydro-lH-[1,2,4]triazolo[1,2-a]pyridazine-1,3(2H)-dione. 5. The method of Claim 1 wherein the compound is 2-(7-chloro-5-fluoro-2,3-dihydro-2-methyl-4-benzo- furanyl)tetrahydro-lH-[1,2,4]triazolo[1,2-a]pyridazine- l,3(2H)-dione. 6. The method of Claim 2 wherein the crop is citrus. 7. The method of Claim 2 wherein the crop is sugarcane. 8. The method of Claim 2 wherein the crop is coffee. 9. The method of Claim 2 wherein the crop is banana. 10. The method of Claim 2 wherein the crop is loblolly pine. 11. The method of Claim 2 wherein the crop is oil palm. 12. The method of Claim 2 wherein the crop is grapes. 13. The method of Claim 4 wherein the crop is citrus. 14. The method of Claim 4 wherein the crop is sugarcane. 15. The method of Claim 4 wherein the crop is coffee. 16. The method of Claim 4 wherein the crop is banana. 17. The method of Claim 4 wherein the crop is loblolly pine. 18. The method of Claim 4 wherein the crop is oil palm. 19. The method of Claim 4 wherein the crop is grapes. 20. The method of Claim 5 wherein the crop is citrus. 21. The method of Claim 5 wherein the crop is sugarcane. 22. The method of Claim 5 wherein the crop is coffee. 23. The method of Claim 5 wherein the crop is banana. 2 . The method of Claim 5 wherein the crop is loblolly pine. 25. The method of Claim 5 wherein the crop is oil palm. 26. The method of Claim 5 wherein the crop is grapes.

Inventors: AMUTI KOFI SAM, AMUTI, KOFI, SAM
Applicants: DU PONT, E.I. DU PONT DE NEMOURS AND COMPANY
Application year: 1992
Main classification: A01N43
IPC codes: A01N43