IL101047A - Method of controlling weeds in plantation crops with 2-(substituted phenyl)-5, 6, 7, 8-tetrahydro-1, 2, 4-triazolo [4,3-a] pyridin-3(2h) ones - Google Patents

Description

101047/2 3fl)-2 o>wtt i>i-i>i O W¾J o*iw jmmb nuv) e>3N(H2)3-1>T >fi[a-4,3]^HNi1\3-4>2,l-m>nKil\3?-8,7,6,5 Method of controlling weeds in plantation crops with 2-(substituted phenyl)-5,6,7,8-tetrahydro-l^,4-triazolo[4,3-a]pyridin-3(2H)ones E.I.DU PONT DE NEMOURS AND COMPANY C.85675 herbicides. Such disclosure is found in U.S. Patent 4,213,773 and U.S. Patent 4,881,967. These patents, however, do not teach use of such herbicides on plantation crops. Plantation crops are an important market and crops such as citrus, sugarcane, coffee, banana, oil palm, etc. are very important to mankind's diet. Also, plantation crops such as rubber are an important source of an industrial raw material. These crops are cultivated particularly in regions of the Pacific rim and South America. A need therefore exists for herbicidal material which are useful for treating plantation crops such as those mentioned.

SUMMARY OF THE INVENTION This invention comprises the novel use of the compound of Formula I and their agriculturally suitable salts for broad spectrum weed control in plantation crops. wherein R is isopropyl, allyl, propargyl or -CH(CH3)C≡CH; X is CI or Br; Y is F or CI; Z . is H or can be taken together with R as -CH2C I HCH3 such that the linking oxygon is attached to the methine carbon; Preferred for reasons of more efficient weed control and/or better crop tolerance are: 1. A method for controlling un desired weeds in plantation crops which comprises applying to the locus of the weeds a herbicidally effective amount of a compound of Formula I wherein X is CI, Y is CI and Z is II. 2. A method of Preferred 1 wherein the plantation crop is selected from citrus, sugarcane, coffee, banana and loblolly pine. 3. A method of Preferred 1 wherein the compound is 2-[2,4- dichloro-5-[(2-propynyl)oxy]phenyl]-5,6,7,8-tetraliydro-l,2,4- triazoloi4,3-a]pyridin-3(2i-r)-one. 4. A method of Preferred 3 wherein the plantation crop is citrus. 5. A method of Preferred 3 wherein the plantation crop is sugarcane. 6. A method of Preferred 3 wherein the plantation crop is coffee. 7. A method of Preferred 3 wherein the plantation crop is banana. 8. A method of Preferred 3 wherein the plantation crop is loblolly pine and the compound is applied preemergent.

DETAILED DESCRIPTION OF THE TNVENTION Synthesis The compounds of Formula I can be prepared according to the procedures of U.S. 4,213,773 and U.S. 4,881,967. The disclosure of which are herein incorporated by reference.

Particularly important compounds for use in this invention include the following: TABLE.! ∑ X Z E CI CI H -CH2CsCH CI CI H -CH2CH=CH2 CI CI H -CH(CH3)CsCH CI CI H -CH(CH3)2 CI CI -CH2CHCH3 I CI F H -CH2CsCH CI F H -CH2CH=CH2 CI F H -CH(CH3)CsCH CI F H -CH(CH3)2 CI F -CH2CHCH3 I Br CI H -CH2CsCH Br CI H -CH2CH=CH2 Br CI H -CH(CH3)CsCH Br CI H -CH(CH3)2 Br CI -CH2CHCH3 -CH2CH-CH2 -CH(CH3)C«CH -CH(CH3)2 -CH2CHCH3 I Formulations Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these 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 will contain these ingredients in the following approximate proportions: Weight Percent* Active Ingredient Diluent(s) Surfactant(s) Wettable Powders 20-90 0-74 1-10 Oil Suspensions, 3-50 40-95 0-15 Emulsions, Solutions, (including Emulsifiable Concentrates) Aqueous Suspension 40-84 1-20 Dusts 1-25 70-99 0-5 Granules and Pellets 0.1-95 5-99.9 0-15 High Strength 90-99 0-10 0-2 Compositions *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 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 powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide", 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0°C. "McCutch eon'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.

The methods of making such compositions are well known.

Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, ginding 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", b miypl Engineering. December 4, 1967, pp. 147ff. and 'Terry'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, March 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; 101047/2 7 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. Khnginan, "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.

In the following examples, all parts are by weight unless otherwise indicated.

Example A Wettable Powder 2-[2,4-dichloro-5-t(2-propynyl)ox ]phenyl3-5,6,7,8-tetrahydro-l,2,4-triazolo[4,3^]pyridin-3(2-f-0-one sodium alkylnaphthalenesulfonate sodium ligninsulfonate synthetic amorphous silica kaolinite The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged.

Wettnblo Powder 2-[2,4-dichloro-5-[(2-propynyl)ox ]phenyl]-5,6,7,8-tetrahydro-l,2,4-triazolo [4,3-β] pyridin-3(2-9r)-one 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 microias in diameter.

The product is reblended before packaging.

Example C Granule Wettable Powder of Example 11 5% attapulgite granules 95% (U.S.S. 20-40 mesh; 0.84-0.42 mm) A slurry of wettable powder containing 25% aolids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.

Example P Extruded Pellet 2-[2,4-dichloro-5-[(2-propynyl)oxy]phenyl]-5,6,7,8-tetraliydro-l,2,4-triazolo[4,3-a]pyridin-3(2H)-one 25% aiihydrous 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 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 ¾ Low Strength Granule 2-[2,4-dichloro-5-[(2-propynyl)oxy]phenyl]-5,6,7,8-tetrahydro-l,2,4-triazolot4,3-a]pyridin-S(2iir)-one 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.

Exam le F Granule 2-[2,4-dichloro-5-[(2-propynyl)oxy]phenyl]-5,6,7,8-tetrahydr triazolu[4,3- ]pyridin-3(2H)-one 80% wetting agent 1% crude h'gninsulfonate salt 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 is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.

Example Q Aqueous Suspension 2-[2,4-dichloro-5-[(2-propynyl)oxy]phenylI-5,6,7,8-tetrahydro-l,2,4-triazolo[4,3-a,pyridin-3(2i_ -one 40% polyacrylic acid thickener 0.3% dodecylphenol polyethylene glycol 0.5% ether disodium phosphate 1% monosodium phosphate 0.5% polyvinyl alcohol 1.0% water 56.7% 1 The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size. ^ gyample ¾ High Strength Concentrate 2-l2,4-dichloro-5-[(2-propynyl)o3ryJphenyl]-5,6)7,8-tetrahyaiu-l,2,4- triazolo[4,3-aJpyridin-3(2J2 one 99% silica aerogel 0.6% 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 furtlier if necessary.

Example I Wettable Powder 2-i2,4-dichloro-5-i(2-propynyl)oxy]phenyl]-5>6,7,8-tetrahydro-l,2,4-triazolo[4,3-a]pyridin-3(2£D-one 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-[2,4-dichloro-5-[(2-propynyl)oxy]phenyl]-5,6)7,8-tetraliydro-l,2,4-triazolo[4,3-a]pyridin-3(2/J)-one 40% sodium ligninsulfonate 20% niontmorillonite 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 Oil Suspension ' 2«[2,4-dichloro-6-[(2-propynyl)oxy]phenyl]-5,6,7f8-tetrabydro-l,2,4- triazolo[4,3-a]pyridin-3(2i?)-one 36% blend of poly alcohol cai-boxylic 6% esters 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 Dust 2-[2,4-dichloro-5-l(2-propynyl)oxy]phenyl]-5,6,7,8-tetrahydiO-l,2,4-triazolo[4,3-o]pyridin-3(2ff)-one 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-l2,4-dicliloro-5-[(2-propynyl)oxy]phenyl]-5,6,7,8-tetrahydro-l,2,4-triazolo[4,3-a]pyridin-3(2#)-one 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.

UTILITY The compounds of the present invention are active herbicides for selective and/or general broadleaf and grass weeds control in all plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, conifers, e.g., loblolly pine, and turf species Kentucky bluegrass, St.

Augustine grass, Kentucky fescue and bermudagrass.

The compounds can be applied as a preemergence or postemergence treatment using techniques of banding, directed sprays or broadcast applications. By selecting the appropriate rate which would be apparent to one skilled in the art, the compounds of this invention can be used in areas where complete control of all 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 and adjuvants, the compounds of this invention can be used for selective weeds control in plantation crops such as citrus, sugarcane, coffee, oil palm, rubber, cocoa, grapes, fruit trees, pineapple, and turf species such as St. Augustine grass, Kentucky bluegrass, bermudagrass, Kentucky fescue. 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 this invention may be used in combination with other herbicides listed below. They are particularly useful in combinations for total vegetation control in plantation crops including: triazine, triazole, uracil, urea, amide, carbamate, bipyridylium, phenoxy, sulfonylurea and imidazole types. They may also be used in combination with mefluidide, glyphosate or gluphosinate. Γητητηοη NPTTI acetochlor 2 cyprazine 2- chloro-4-(cyclopropylamino)-6-(isopropyl- amino)-a-triaziiie cyprazole N-[5-(2-chloro-l,l-dimethylethyl)-l,3,4- thiadiazol-2-yl]cyclopropanecarboxamide cypromid 3 ,4'-dichlorocydopropanecarboxaiulide dalapon 2,2-dichloropropanoic acid dazomet tetrahydro-3 ,5-dimethyl-2H-l ,3 ,5-thiadiazine-2- thione DCPA dimethyl 2,3,5,6-tetrachloro-l,4-beazene- dicarboxylate desmediphan ethyl [3-[[(phenylamino)carbonyl]oxy]phenyl]- carbamate desmetryn 2-(isopropylamino)-4-(methylamino)-6-(methyl- thio)-s-triazi e diallate S-(2,3-dichloro-2-propenyl)bis(l-methylethyl)- carbamothioate Γ,ητηττ^ρ Nam? h Tnirfl Nam? dicamba 3 ,6-dichloro-2-methoxybenzoic acid dichlobenil 2.6- dichlorobenzonitrile dicbJorprop (±)-2-(2 ,4-dichloropheno3-y)propanoic acid dichlofop (±)-2-[4-(2,4-dichlorophenoxy)pb.enoxy]propanoic acid, methyl ester diethatyl N-(chloroacetyl)-N-(2,6-diethylphenyl)glycine difenzoquat 1 ,2 -dimethy 1-3 ,5 - diphenyl- lH-pyrazolium dimepiperate S- 1 -methyl- 1 -phenylethylpiperidine- 1 -carbo- thioate dinitr amine N3,N3-diethyl-2,4-dinitro-6-(trifluoromethyl)- 1 ,3-benzenedi amine dinoseb 2-(l-methylpropyl)-4,6-dinitrophenol diphenamid Ν,Ν-dimethy 1-a-pheny lbenzene acetami de dipropetryn e-iethylthioi-N.N'-bisd-methylethyD-l.S.S- triazine-2 ,4-diamine diquat 6.7- dihydrodipyrido[l,2-a:2',l'-c]-pyTazinedivim ion diuron N'-(3,4-dichlorophenyl)-N,N-dimethyliirea DNOC 2-methyl-4,6-dinitrophenol Cfrmmop Nffimft C gmicftl Name DSMA disodium salt of MAA dymron N^met ylphenylJ-N'-il-methyl-l-pheny!- ethyl)urea endothall 7-oxabicyclo[2.2.13heptane-2,3-dicarboxylic acid EPTC S-ethyl dipropylcarbamothioate esprocarb S-benzyJ-N-ethyl-N-(l,2-dimethyl)propyl)thiol- carbamate etbalfluralin N-ethyl-N-(2-methyl-2-propenyl)-2,6-dinitro-4- (trifluoromethyl)benzenairune ethoftimesate (±)-2^thoxy-2,3-diiiydro.3)3-diinethyl-5- benzofuranyl methanesulfonate Express® 2-[[[[N-(4-methoxy-6-methyl-l,3,5-triazine-2-yl)- N-methylamino]carbonyl]aini o]sulfonyl3ben2oic acid, methyl ester fenac 2,3,6-trichlorobenzeneacetic acid fenoxaprop (±)-2-[4-[(e-chloro-2-benzoxazoIyl)oxy3phenoxy]> propanoic acid fenuron N,N-dimethyl-N'-phenylurea fenuron TCA Salt of fenuron and TCA flamprop N-benzoyl-N-(3-chloro-4-fluorophenyl)-DL- alanine fluazifop (i)-2-[4-[[5-(trifluoromethyl)-2-pyridinyI]oxy]- phenoxyjpropanoic acid C¾ftm½1 Name fliiazi op-P (R)-2-[4-[[5-(trifluoromethyl)-2-pyridinyl]oxy]- phenoxy]propanoic acid flucbJoralin N-(2-chloroethyl)-2 ,6-dinitro-N-propyl-4- (trifluoromethyl)benzenamine fluometuron N^-dimethyl-N 3-(trifluoromethyl)- phenyljurea fluorochloridone 3-chloro-4-(chloromethyl)-l-[3-(trifluoro- methyl)phenyl]-2-pyrrolidinone fluorodifen -nitrophenyl a,a,a,-trifluoro-2-nitro-p-tolyl ether fluoroglycofen carboxymethyl 5-[2-chloro-4-(trifluoro- methyl)phenoxy]-2-nitrobenzoate fluridone 1- methyl-3-phenyl-5-[3-(trifluoromethyl)- phenyl]-4( lH)-pyridinone fomesafen 5 - [2 -chloro-4-( trifluoromethyl )phenoxy ]-N- (methylsulfonyl)-2-nitrobenz amide fosamine ethyl hydrogen (aminocarbonyDphosphate glyphosate N-(phosphonomethyl)glycine haloxyfop 2- [4-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl]- oxy]phenoxy]propanoic acid Harmony® 3- [[[[(4-methoxy-6-methyl-l,3,5-triazin-2-yD- amino]carbonyl]ainino]sulfonyl]-2-thiophene- carboxylic acid, methyl ester Common PTT hexaflurate potassium hexailuoroarsenate hexazinone 3- cyclohexyl-6-(dimetiiylamino)- 1-methyl- 1 ,3 ,5- triazine-2,4( lH,3H)-dione imazamethabenz 6^4 3opropy -methyl-5^xo-2-imidazolin-2-yl)- m-toluic acid, methyl ester and 6-(4-isopropyl-4- methyl-5-oxo-2-miidazolin-2-yl)-p-toluic acid, methyl ester unazapyr (±)-2-[4,5-d ydro-4-methyl-4-(l-methylethyl)-5- oxo-lH-ixoidazol-2-yl]-3-pyridinecarboxylic acid lmazaquin 2- [4,5-dihydro-4-methyl-4-(l-methylethyl)-5-oxo- lH-imidazol-2-yl]-3-qu olmecarboxylic acid imazethapyr (±)-2-[4,5-dihydro-4-methyl-4-(l-methylethyl)-5- oxo-lH-imidazol-2-yl]-5-ethyl-3- pyridinecarboxylic acid ioxynil 4- hydroxy-3,5-diiodobenzonitrile isopropalin 4-(l-methylethyl)-2,6-dinitro-N,N-dipropyl- benzenamine isoprotxiron N-(4-isopropylphenyl)-N',N'-dimethylurea isouron N'-[5-(l,l.dimethylethyl)-3-isoxazolyl]-N,N- dimethylurea isoxaben N-[3-(l-ethyl-l-methylpropyl)-5-isoxazolyl]-2,6- dimethoxybenz amide karbutilate 3- [[( dimethylaimno)carbonyl]aimi-o]phenyl-( 1,1- dimethylethyl)carbamate lactofen (±)-2-ethoxy-l-methyl-2-oxoethyl 5-[2-chloro-4- (trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical Name lenacil 3- cyclohexyl-6,7-dihydro-lH-cyclopenta- pyrimidine-2,4(3H,5H)-dione linuron N'-(3,4-dichlorophenyl)-N-methoxy-N-metliyl- urea MAA methylarsonic acid MAMA monoammonium salt of MAA MCPA (4-chloro-2-methylphenoxy)acetic acid MCPB 4- (4-chloro-2-methylphenoxy)butanoic acid MON 7200 S,S-dimethyl-2-(difluoromethyl)-4-(2-methyl- propyl)-6-(trifluoromethyl)-3,5-pyridinedicarbo- thionate mecoprop (±)-2-(4-chloro-2-methylphenoxy propanoic acid mefenacet 2-(2-benzothiazolyloxy-N-methyl-N-phenyl- acet mide mefluidide N-[2,4-diinethyl-5-[[(trifluoromethyl)sulfonyl]- amino]phenyl]acetamide methalprop alin N-(2-methyl-2-propenyl)-2,6-diiiitro-N-propyl-4- (trifluoromethyl)benzenamide methabenzthiazuron l,3-(umethyl-3-(2-benzothiazolyl)urea metham methylcarbamodithioic acid methazole 2-(3 ,4-dichloropheny l)-4-methyl- 1 ,2 ,4-oxa- diazolidine-3,5-dione Γητητηηη Nfl Chemical Name methoxuron N'^S^oro^-methoxjrheny -N^-Kiimeth l- rea metolachlor 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2- methoxy-l-methylethyl)acetamide metribuzin 4- amino-6-( 1 -diniethylethyl)-3-(methylthio)- 1 ,2 ,4-triazin-5(4H)-one metsul uron methyl 2- [[[[(4-methoxy-6-methyl-l ,3 ,5-triazin-2-yD- ammo]carbonyl]amiiio]sxilfonyl]benzoic acid, methyl ester MH 1 ,2-dihy dro-3 ,6-pyridazinedione molinate 5- ethyl hexahy dro- IH-azepine- 1-carbothioate monolinuron 3- (£-chlorophenyl)-l-methoxy-l-methylurea monuron N'-(4-chlorophenyl)-N,N-dimethyl irea monuron TCA Salt of monuron and TCA MSMA monosodium salt of MAA napropamide N,N-diethyl-2-(l-naphthalenyloxy)propanamide naptalam 2-[( 1-naphthaleny lamino)carbonyl]benzoic acid neburon l-butyl-3-(3,4-dichlorophenyl)-l-methylurea nitralin 4- (methylsulfonyl)-2,6-dinitro-N,N-dipropyl- aniline nitrofen 2,4-dichloro-l-(4-nitrophenoxy)benzene f!hpmiral Nu p ziitroiluorfen 2 bJoro-1^4-nitrophenoxy)-4-(trifluoro- methyDbenzene norea N^-dimetbyl-N'-(octahydro-4,7-methario-lH- inden-5-yl)urea 3aa,-4a,5a,7a,7aa-isomer norflurazon 4 TABLE OF COMPOUNDS CMPD m.p.(°C) 1 -CH2C≡CH CI 167-169 2 -CH2CH=CH2 CI oil 4 -CH(CH3)2 CI oil 5 -CH2CH=CH2 F oil Compound 3 (m.p. 158-159°C) TEST A Seeds of legume cover r™pB Ρη^τηπλ jflvpnr* and C'al?rPg"nT"m mucunoides were planted in 11.4 cm square pot filled with greenhouse planting medium. PflfiPfl im CftPjttgfltVJB cuttings were planted in 15.2 cm plastic pots filled with the same planting medium.

Plants were sprayed postemergence with the test compounds in a non-phytotoxic solvent. Treated plants were visually rated 14 days-after-treatment (DAT) and compared with the appropriate controls. The injury ratings were 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 A.

TABLE A Plant Iniurv Rating Rate Pueraria Calapogonium Paspalum Compound g/ha javanica mucunoides c^pj ygpt- p 250 80 90 30 280 100 100 0 TEST B Rhizones of lalang flinperflta c Hfldrica) and stem cuttings of ikaT ifl spp. were planted in separate 15.2 cm plastic pots filled with greenhouse planting medium and grown in the greenhouse. The ffifcnnifl spp. was profusely vining and the lalang had profusely growing rhizones at the time of treatment.

The plants were sprayed postemergence with the test compound in a non-phytotoric solvent. The treatments were visually rated 24 DAT and compared with the appropriate controls. Plant injury ratings were based on the scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal injury and 100 indicates complete control. The results are shown in Table B.

TABLE B Rate Plant Iniurv Rating Compound g/ha Mikania spp. Lgjajig 1 250 70 0 TEST C Stem cuttings of Mikania spp. and Boston fern (Nephrolepis exaltata) were planted in separate 15.2 cm plastic pots filled with greenhouse planting medium and grown in the greenhouse.

The plants were sprayed postemergence with the test compounds in a non-phytotoxic solvent. The treated plants were visually rated 49 DAT and compared with appropriate controls. The plant injury ratings scale used in Table A was used in this test also. The results are shown in Table C.

TABLE C Rate Plant Iniurv Rating Compound g/ha Mikania spp. Boston fern 1 1000 80 90 500 70 70 250 50 70 2 1000 40 30 500 20 10 250 10 10 TEST D Loblolly pine (Pinus taeda). pecan (Carya spp.), Swamp oak fOuercus spp.), white ash ίΡτ ηηιιρ ajn jacjufi) and eweetgum fLiqviflpmfrflr strvaciflua) seedlings were planted in 30-liter plastic pot filled with planting medium. The plants were grown in the greenhouse for five months before spraying.

Plants were sprayed postemergence with Compound 1 formulated in a non-phytotoxic solvent. The treated plants were visually rated 99 DAT and compared with appropriate controls. Plant injury ratings scale used in Test A was used in this test also. The results are shown in Table D.

TABLE P Species 500 250 125 Loblolly pine 50 30 0 Pecan 0 0 0 Swamp oak 0 0 0 White ash 0 0 0 Sweetgum 0 0 0 TEST E Guineagrass (PaTiimm maTimnm) seeds and elephantgrass rooted cuttings were planted in separate 15.2 cm plastic pots filled with greenhouse planting soil.

The plants were treated postemergence with Compound 1 formulated in a non-phytotoxic solvent. The guineagrass (P.. ma imum) was treated preemergence and at early and late growth stages postemergence. Treated plants were visually rated 32 DAT and compared with appropriate controls. Plant injury ratings used in Test A were also used in this test. The results are shown in Table E.

TABLE E 500 250 125 g ha Preemergence Guineagrass 100 100 100 Postemerfence Guineagrass (early) 100 100 30 (late) 30 10 10 Elephantgrass 30 30 30 TEST F Stem cuttings of St. Augustine grass and Alexander grass ffirflfbjflrifl plantagenea). Kentucky bluegrass sod and seeds of Kentucky fescue, annual bluegrass, bermudagrass, bentgrass, large crabgrass and smooth crabgrass were planted in individual 11.4cm square plastic pots. The plants were grown in the greenhouse until used.

The plants were sprayed postemergence with Compound 1 formulated in a non-phytotoxic solvent. The treated plants were visually rated 29 DAT compared with appropriate controls. The rating scale used in Test A was also used in this test. The results are shown in Table F.

TABLE F Compound 1 Species 500 250 125 64 g/ha St. Augustine grass 70 50 0 0 0 Kentucky bluegrass sod 70 50 20 0 0 Kentucky fescue 100 90 80 30 20 Bermudagrass 80 70 80 20 0 Bentgrass 100 100 100 80 20 Annual bluegrass 100 90 100 60 0 Alexandergrass 30 30 20 20 0 Large crabgrass 100 100 100 100 100 Smooth crabgrass 100 100 100 100 100 TEST G Seeds of guineagrass (£. ma-x-imnm were planted in 15.2 cm plastic pots filled with planting medium, planting was done in two stages. Sugarcane stem cutting, and goldenrod (Solidago spp.) stem and rhizone cuttings were also planted in 15.2 cm plastic pots filled with planting medium. Plants were cut back often to stimulate ratoon production in the sugarcane and vigorous growth in paspalum and goldenrod.

Plants were treated postemergence with Compound 1 in a non-phytotoxic spray solvent. The treatments were visually rated 20 DAT and compared with appropriate controls. The plant injury ratings were based on the scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal injury and 100 indicates complete control. The results were shown in Table G.

TABLE G Species 1000 500 250 125 g/ha Sugarcane 10 10 10 10 Guineagrass (early) 100 100 100 100 (late) 80 70 20 10 Goldenrod 0 0 0 0 Paspalum 0 0 0 0 TEST H Rooted cutting of rough lemon (Citrus spp.) were planted in 30-liter plastic pots and also in 11.4 cm square plastic pots. The 30-liter pots were also seeded with pigweed yjridig), eandbur (Ceachrag gc iaafas), Texas panicum f «nir^m texanum). narrowleaf panicum (£. seeds and yellow nutsedge (Cyperus esculentus) tubers.

The citrus in the 30-liter pots were sprayed to simulate the trunk-to-trunk herbicide application method used in citrus groves, while the weeds were treated preemergence. The citrus in the 11.4 cm square pots were given direct over the top treatments. All pots were treated with Compound 1 formulated in a non-phytotoxic spray solvent. Plants were visually rated 28 DAT and compared with appropriate controls. The injury rating scale used in Test A was also used. The results are shown in Table H.

TABLE H Compound 1 500 250 125 g/ha Preemergence Citrus 0 0 0 0 Yellow nutsedge 80 60 30 0 Pigweed 100 100 100 100 Sandbur 100 100 100 100 Texas panicum 100 100 100 100 Narrowleaf panicum 100 100 100 100 Postemergence Citrus 0 0 0 0 TEST I Μ*½ΐηΐλ spp. vine cuttings, Boston fern (& exaltata) and coffee (Coffea spp.) were planted separately in 15.2 cm plastic pots. Compound 1 was applied postemergence to the plants using 30 psi and 40 psi spray pressure.

In this test Compound 1 was formulated with 0.25% X-77 surfactant. Plants were visually rated 32 DAT and compared with appropriate controls. The injury rating scale used in Test A was used in this test. The results are shown in Table I.

TABLE I Compound 1 500 250 125. g/ha 30 psi spray Mikania 70 50 40 Boston fern 30 10 10 Coffee 0 0 0 40 psi spray Mikania 80 70 40 Boston fern 90 60 20 Coffee 0 0 0 TEST J Rooted rough lemon cuttings were planted in 30-liter plastic pots.

The pots were also seeded with Texas panicum, guineagrass, pigweed (Δ· viridis)T sandbur and yellow nutsedge tubers. i^anin spp. vine cutting and Boston fern were planted in 15.2 cm plastic pots. The plants were treated postemergence with Compound 1 formulated in non-phytotoxic spray solvent. Texas panicum, guineagrass and pigweed were seeded into the 30-liter pots and treated preemergence.

Plants were visually rated 35 DAT compared with appropriate controls. The injury ratings were based on the scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal injury and 100 indicates complete control. The results are shown in Table J.

TABLE J Compound 1 1000 500 250 125 g/ha Postemergen e Rough lemon 30 30 30 0 Guineagrass 100 100 0 0 Sandbur 100 100 100 - Pigweed 100 100 100 100 Texas panicum 100 70 60 0 Yellow nutsedge 70 0 0 0 Mikania 90 80 80 60 Boston fern 90 80 60 30 Preemerpence Texan panicum 100 100 100 100 Guineagrass 100 100 100 100 Pigweed 100 100 100 100 TEST K Stem cuttings of St. Augustine grass, Kentucky bluegrass sod, seeds of Kentucky fescue, bentgrass, bermudagrass, large crabgrass, smooth crabgrass, dallisgrass and blackseed plantain transplants were planted separately in 11.4 cm square pots filled with planting medium. Plants were treated postemergence with Compound 1 formulated in a non-phytotoxic spray solvent.

The treated plants were visually rated 24 DAT and compared with appropriate controls. The rating scale used in Test F was used in this test also. The results are shown in Table K. The variations in these results from those observed with Test F could be due to the fact that the tests were conducted at different times of the year.

TABLE K Compound 1 125 M 1 g/ha St. Augustine grass 30 30 30 Kentucky bluegrass sod 50 20 20 Kentucky fescue 0 0 0 Bentgrass 20 0 0 Bermudagrass 30 0 0 Large crabgrass (early) 100 60 40 (late) 40 0 0 Smooth crabgrass (early) 70 50 0 (late) 20 0 0 Dallisgrass 100 40 0 Blackseed plantain 0 0 0 TEST L Plastic windowsill flats were filled with planting medium and seeded with corn, johnsongrass, ehattercane, sorghum, giant foxtail, wild proso millet, large crabgrass, velvetleaf and sugarcane node cutting at the spike stage. In a second test, windowsill flats were seeded with untreated and antidote seed-treated corn, johnsongrass, velvetleaf, Williams soybean, W-20 and W-4 soybean, wild proso millet, cocklebur, untreated and antidote seed-treated sorghum, morningglory, ehattercane, giant foxtail lambsquarters and sugarcane node cuttings at the spike stage.

The plants were treated preemergence with Compound 1 formulated in a non-phytotoxic spray solution. Treatments were visually rated 24 and 41 DAT and compared with appropriate controls. The injury ratings were based on the 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 La and Lb.

TABLE La Compou d 1 125 g/ha Corn 30 0 0 Johnsongrass 100 80 70 Shattercane 100 70 0 Sorghum 100 0 0 Giant foxtail 100 100 100 Wild proso millet 100 90 70 Large crabgrass 100 100 100 Velvetleaf 100 100 100 Sugarcane 0 0 0 TABLE Lh 500 250 125 £5 22 g ha Untreated corn 60 50 10 0 0 Treated corn 0 0 0 0 0 Johnsongrass 100 100 80 60 60 Velvetleaf 100 100 100 100 100 Williams Soybean 100 100 80 30 20 W-20 100 100 100 30 0 W-4 100 100 100 100 0 Wild proso millet 100 100 100 100 0 Cocklebur 70 70 20 20 0 Untreated Sorghum 100 100 0 0 0 Treated Sorghum 100 100 0 0 0 Morningglory 100 100 70 70 30 Shattercane 100 100 50 50 20 Giant foxtail 100 100 100 100 80 Lambsquarters 100 100 100 100 100 Sugarcane 30 0 0 0 0 TEST M The object of this test was to evaluate the effect of pre-plant-incorporation of Compound 1 on loblolly pine and rough lemon plants. Soil was sprayed with Compound 1. The treated soil was mixed thoroughly in plastic bags to incorporate the compound into the soil. Loblolly and rough lemon plants were then transplanted into the Compound 1 treated soil. Plants were visually rated 66 DAT and compared with the appropriate controls. The injury ratings were based on the same scale as used in Test L. The results are shown in Table M.

Kate Loblolly Rough Compound g/h Pine Lemon 1 500 20 0 250 0 0 125 0 0 64 0 0 32 0 0 TEST N Rough lemon rooted cuttings were planted in 30-liter plastic pots. The pots were also seeded with Spanish needles (Bidens pjlojga), pigweed (A- viridis). narrowleaf panicum, Texas panicum, guineagrass, sandbur and purple nutsedge tubers. Mikania spp. vine cutting and Boston fern were planted in separate 15.2 cm plastic pots.

The plants were treated postemergence with Compound 1 formulated in a non-phytotoxic spray solution. The 30-liter pots were treated to simulate the trunk-to-trunk type treatment used in some citrus groves. Treatments were visually rated 37 DAT and compared with the appropriate controls. The rating scale used in Test L was used in this test also. The results are shown in Tables Na and Nb. The variations in these results from those observed for other tests could be due to the fact that the tests were conducted during different months of the year and on different growth size of plants at time of treatment. Greenhouse test s are conducted on a year-round basis (12 calendar months). These tests are repeated anytime of the year and not at the exact time when the test was first conducted. lABLEJia Compound 1 1000 500 250 g/ & Rough lemon 0 0 0 Spanish needles 0 0 0 Pigweed 100 100 100 Narrowleaf panicum 100 100 100 Texas panicum 90 80 80 Guineagrass 100 100 100 Sandbur 100 100 100 Purple nutsedge 0 0 0 Mikania 80 70 50 Boston fern 90 80 80 TABLE Nb Compound 1 500 25Ω g/ha Rough lemon 0 0 0 Texas panicum 80 60 20 Spanish needles 20 10 0 Narrowleaf panicum 90 80 10 Pigweed 80 80 20 Guineagrass 90 80 10 Sandbur 100 70 - TEST O Large fiberglass tubs filled with planting medium were planted with seed potato and seeded with ragweed, black nightshade, wild proso millet, giant foxtail and barnyardgrass. In another test, the tubs, were planted with seed potato and volunteer pigweeds allowed to grow. The tubs were treated preemergence with Compound 1 formulated in a non-phytotoxic spray solvent. Plants were visually rated 34 and 66 DAT compared with appropriate controls. The injury ratings scale used in Test A was used in this test. The results are shown in Table Oa and Ob.

TABLE Oa Compound 1 250 125 g/h Potato 70 50 Ragweed 100 100 Black nightshade 100 100 Wild proso millet 100 100 Giant foxtail 100 100 Barnyardgrass 100 100 TABLE Ob Compound 1 125 24 22 g ha Potato 30 10 0 Pigweed 100 100 100 TEST P Plastic tray liners with individual planting compartments were filled with planting medium and seeded separately with bermudagrass (CyBodOB dactvlon). broadleaf eignalgrass (Brachiaxia platvphvlla). guineagrass ( animm m TTwnm^ smooth crabgrass (Digitaria ipchflPTTmm), barnyardgrass (Echinnclna cnis^gfllli), large crabgrass (P_.

(Snrghu halepense). Texas panicum fP niniTn tgsajuuo), sandbur (Cenchrus gchinatusV itchgrass (Rottbpellia goosegrass (Eleusine iadicfl), dalliegrass Tflflppl" dilaifiillBl), annual bluegrass (P_o_a ann .), alfalfa (Medicago gaUza), Pueraria favani morningglory (Ipomea spp.), purslane (Portulaca oleracea). field bindweed (Convolvulus arvensis). ragweed (Ambrosia fila ioj-), peanut Arachis hvpogea). purple nutsedge (Cvperus rotundus). yellow nutsedge (£. esculentus). and Kentucky bluegrass sod (Poa pratense). Sugarcane node cuttings were planted in 15.2 cm plastic pots filled with planting medium.

The plantings were tested peremergence and postemergence with the compounds formulated in a non-phytotoaric spray solution. Plantings were staggered so that the preemergence and postemergence treatments were sprayed on the same day. Plants were visually rated 18 to 29 days after treatment (DAT) and compared with appropriate controls. The injury ratings were 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 variations in these results could be due to the fact that the tests were conducted at different times of the year and on plants at different growth stages. The results are shown in Tables Pa-Pr.

!AELE-Ea Compound 1 1000 500 250 1000 500 25_0_ g hfl Preemergence Postemergence Bennudagrass 100 100 100 100 100 100 Broadleaf signalgrass 100 100 100 100 100 100 Guineagrass 100 100 100 100 100 100 Smooth crabgrass 100 100 100 100 100 100 Barnyardgrass 100 100 100 100 100 100 Large crabgrass 100 100 100 100 100 100 Johnsongrass 100 100 100 100 100 100 Texas panicum 100 100 100 100 100 100 Sandbur 100 100 100 100 100 100 Itchgrass 100 100 100 80 80 70 Kentucky bluegrass sod - - - 60 50 20 Alfalfa 100 100 100 30 30 0 Pueraria javanica 100 100 100 - - - Morningglory 100 100 100 100 100 60 Purslane 100 100 100 100 100 100 Field bindweed 100 100 100 100 100 100 Ragweed 100 100 100 100 100 100 Purple nutsedge 70 60 50 40 30 0 Yellow nutsedge 80 50 40 70 40 30 TABLE Pb Compound 1 18. £ S Postemergence Bermudagrass 40 20 0 Broadleaf signalgrass 0 0 0 Guineagrass 0 0 0 Smooth crabgrass 0 0 0 Large crabgrass 0 0 0 Johnsongrass 0 0 0 Goose grass 0 0 0 Yellow nutsedge 0 0 0 Compound 1 500 250 125 JafiQ 25Q 125 gZha Preemergence Postemergence Bermudagrass 100 100 100 100 100 100 Broadleaf signalgrass 100 100 100 100 100 100 Guineagrass 100 100 100 100 100 100 Smooth crabgrass 100 100 100 100 100 100 Large crabgrass 100 100 100 100 100 100 Johnsongrass 100 100 100 100 100 100 Texas panicum 100 100 100 100 100 100 Sandbur 100 100 100 100 100 100 Itchgrass 100 100 100 100 100 80 Dallisgrass 100 100 100 100 100 100 Kentucky bluegrass sod - - - 40 30 0 Sugarcane - - - 80 20 0 Alfalfa 100 100 100 100 100 100 Pueraria javanica 100 100 100 -Morningglory 100 100 100 100 100 100 Purslane 100 100 100 100 100 100 Field bindweed 100 100 100 100 100 100 Ragweed 100 100 100 100 100 100 Purple nutsedge 60 50 0 70 - -Yellow nutsedge 40 30 20 100 100 40 !ABLELEd Compound 1 500 250 125 64 Preemergence Bermudagrass 100 100 100 100 80 Broadleaf signalgr, 100 100 100 80 60 Guineagrass 100 100 100 100 100 Smooth crabgrass 100 100 100 100 100 Large crabgrass 100 100 100 100 100 Johnsongrass 100 100 100 90 70 Texas panicum 100 100 100 100 100 Sandbur 100 100 100 80 0 Itchgrass 100 100 100 60 40 Dallisgrass 100 100 100 100 100 Alfalfa 100 100 100 100 100 Pueraria javanica 100 100 100 0 0 Morningglory 100 100 100 80 60 Purslane 100 100 100 100 100 Field bindweed 100 100 100 60 60 Ragweed 100 100 100 100 100 Purple nutsedge 70 70 - 0 0 Yellow nutsedge 70 50 30 40 20 lA£LELEe Compound 1 250 125 £4 22 Postemergence Bermudagrass 100 100 60 60 70 Broadleaf signalgrass 100 100 100 100 80 Guineagrass 100 100 90 70 60 Smooth crabgrass 100 100 80 50 70 Large crabgrass 100 100 100 100 100 Johnsongrass 100 100 70 50 40 Texas panicum 100 100 90 90 0 Sandbur 100 100 80 80 70 Itchgrass 70 70 60 20 0 Dallisgrass 100 100 100 100 0 Kentucky bluegrass sod 60 40 0 0 0 Alfalfa 70 40 0 50 0 Morningglory 100 100 100 100 100 Purslane 100 100 100 100 100 Field bindweed 100 100 100 100 100 Ragweed 100 100 100 100 100 Purple nutsedge 60 50 30 0 0 Yellow nutsedge 90 70 30 0 0 TABLE Pf Compound 1 500 250 125 500 250 125. gi & Preemergence Postemergence Bermudagrass 100 100 100 100 100 0 Broadleaf signalgrass 100 100 100 100 100 70 Guineagrass 100 100 100 100 100 60 Smooth crabgrass 100 100 100 100 100 50 Large crabgrass 100 100 100 100 100 20 Johnsongrass 100 100 100 70 70 40 Texas panicum 100 100 100 100 100 70 Itchgrass 100 100 100 70 70 50 Goosegrass 100 100 100 - - -Dallisgrass 100 100 100 100 100 100 Kentucky bluegrass sod - - - 30 30 0 Sugarcane Alfalfa 100 100 100 50 40 0 Pueraria javanica 100 100 100 - - -Morningglory 100 100 100 100 100 40 Purslane 100 100 100 100 100 100 Field bindweed - - - 100 100 100 Ragweed 100 100 100 100 100 80 Purple nutsedge 50 0 0 60 0 0 Yellow nutsedge 60 60 0 60 50 0 δ Compound 1 500 250 125 500 250 125. g/ha Preemergence Postemergence Bermudagrass 100 100 100 100 100 80 Broadleaf eignalgrass 100 100 100 100 100 100 Guineagrass 100 100 100 100 100 100 Smooth crabgrass 100 100 100 100 100 70 Large crabgrass 100 100 100 100 100 90 Johnsongrass 100 100 100 100 100 100 Texas panicum 100 100 100 100 100 100 Sandbur 100 1 100 90 - - - Itchgrass 100 100 90 100 90 80 Goosegrass 100 100 100 100 100 100 Dallisgross 100 100 100 100 100 100 Annual bluegrass 100 100 80 100 100 100 Kentucky bluegrass sod - - - 90 30 20 Sugarcane - - - 50 10 0 Alfalfa 100 80 80 80 70 10 Pueraria javanica 100 90 70 - - - Morningglory 100 70 30 100 90 80 Purslane 100 100 100 100 100 100 Ragweed 100 100 100 100 100 90 Peanut 70 80 50 90 60 30 Purple nutsedge - - - 30 10 10 Yellow nutsedge - - 50 20 0 5 2 BLE-Eh Compound 1 250 250 gZtkfi Preemergence Postemergence BerznudagrasB 100 100 Broadleaf signalgrass 100 100 Guineagrass 100 100 Smooth crabgrass 100 90 Large crabgrass 100 90 Johnsongrass 100 100 Texas panicum 100 100 Sandbur 80 100 Itchgrass 90 90 Goosegrass 100 100 Dallisgrass 100 100 Annual bluegrass 70 100 Kentucky bluegrass sod 10 Alfalfa 50 20 Pueraria javanica 20 Morningglory 0 80 Purslane 100 90 Ragweed 20 100 Peanut 20 70 Purple nutsedge 10 Yellow nutsedge 80 TABLE Pi Compound 1 — 250 2Sfi Preemergence Postemergence Bermudagrass 100 80 Broadleaf signalgrass 100 40 Guineagrass 100 30 Smooth crabgrass 100 20 Large crabgrass 100 80 Johnsongrass 100 100 Texas panicum 100 100 Sandbur 100 80 Itchgrass 90 100 Goosegrass - 40 Dallisgrass 100 50 Annual bluegrass 0 10 Kentucky bluegrass sod - 0 Alfalfa 90 60 Pueraria javanica 30 - Morningglory 100 100 Purslane 100 100 Ragweed 100 100 Peanut 10 50 Purple nutsedge - 60 Yellow nutsedge - 90 TABLE Pi Compound 2 1000 500 250 1000 500 250.

Preemergence Postemergence Bermudagrass 100 100 100 100 100 40 Broadleaf signalgrass 100 100 100 100 100 40 Guineagrass 100 100 100 100 100 30 Smooth crabgrass 100 100 100 100 100 60 Barnyardgrass 100 100 100 100 100 40 Large crabgrass 100 100 100 100 100 80 Johnsongrass 100 100 100 100 60 30 Texas panicum 100 100 100 100 100 60 Sandbur 100 100 100 100 100 40 Itchgrass 100 100 100 70 50 0 Kentucky bluegrass sod - - - 60 30 0 Alfalfa 100 100 100 100 50 50 Pueraria javanica 100 100 100 - - -Morningglory 100 100 60 100 100 30 Purslane 100 100 100 100 100 100 Field bindweed 100 100 100 100 100 100 Ragweed 100 100 70 70 60 0 Purple nuteedge 60 50 0 20 0 0 Yellow nutsedge 60 30 0 60 30 0 TABLED Compound 2 5_0_Q 25Ω 125 5_0_0_ 250. 125 gih& Preemergence Postemergence Bermudagrass 100 100 100 10 90 0 Broadleaf signalgrass 100 100 100 100 70 0 Guineagrass 100 100 100 90 0 0 Smooth crabgrass 100 100 90 0 0 0 Large crabgrass 100 100 80 80 20 0 Johnsongrass 100 40 50 100 40 0 Texas panicum 100 100 70 100 70 0 Sandbur 100 100 100 - - - Itch grass 100 70 30 50 10 0 Goosegrass 100 100 100 100 80 0 Dallisgrass 100 100 80 90 20 0 Annual bluegrass 60 20 0 70 30 0 Kentucky bluegrass sc - - - 20 0 10 Sugarcane - - - 0 0 0 Alfalfa 70 30 0 20 20 0 Pueraria javanica 50 20 0 - - - Morningglory 70 10 10 100 90 20 Purslane 100 100 100 100 100 80 Ragweed 100 30 20 80 80 10 Peanut 40 30 10 60 10 0 Purple nutsedge - - - 10 0 0 Yellow nutsedge - - - 60 0 0 TABLE PI Compound 2 Preemergence Postemergence Bermudagraes 100 0 Broadleaf signalgrass 90 20 Guineagrass 100 30 Smooth crabgrass 100 0 Large crabgrass 60 10 Johnsongrass 20 10 Texas panicum 100 30 Sandbur 10 0 Itch grass 40 0 Goosegrass 100 80 Dallisgrass 90 10 Annual bluegrass 0 0 Kentucky bluegrass sod - 0 Alfalfa 0 20 Pueraria javanica 0 orningglory 0 20 Purslane 100 60 Ragweed 40 10 Peanut 0 20 Purple nuteedge - 0 Yellow nuteedge - 0 TABLE Pm Compound 5 . 500 250 125 £0_0_ 25J_ 125 gl & Preemergence Postemergence Bermudagrass 100 100 100 0 0 0 Broadleaf signalgrass 100 90 90 100 60 0 Guineagrass 100 100 100 100 0 0 Smooth crabgrass 100 100 100 20 0 0 Large crabgrass 100 100 100 60 30 0 Johnsongrass 90 80 80 100 80 20 Texas panicum 100 100 100 100 80 0 Sandbur 40 40 20 - - - Itchgrass 70 60 30 40 0 10 G osegrass 100 100 100 100 20 30 Dallisgrass 100 90 70 90 90 10 Annual bluegrass 60 10 10 100 20 0 Kentucky bluegrass sod - - - 0 0 0 Sugarcane - - - 0 0 0 Alfalfa 0 20 0 50 50 0 Pueraria javanica 90 10 0 - - - Morningglory 90 20 10 100 100 100 Purslane 100 100 100 100 100 100 Ragweed 100 80 90 100 - 60 Peanut 40 30 20 60 50 20 Purple nutsedge 10 0 0 Yellow nutsedge 30 20 20 TABLE Pn Compound 3 125 12& Preemergence Postemergence Berznudagrass 100 0 Broadleaf eignalgrass 70 20 Guineagrass 100 20 Smooth crabgrass 100 0 Large crabgrass 100 0 Johnsongrass 100 0 Texas panicum 100 90 Itchgrass 60 30 Goosegrass 100 Dallisgrass - 0 Kentucky bluegrass sod - 0 Alfalfa 100 70 Pueraria javanica 0 Morningglory 100 100 Purslane 100 100 Field bindweed - 100 Ragweed 100 100 Purple nutsedge 0 0 Yellow nutsedge 0 0 TABLE Po Compound 3 125 125 g/ha Preemergence Postemergence Bermudagrass 100 0 Broadleaf signalgra: 100 100 Guineagrass 100 10 Smooth crabgrass 100 0 Large crabgrass 100 50 Joh songrass 100 100 Texas panicum 100 100 Sandbur 90 Itchgrass 90 30 Goosegrass 100 100 Dallisgrass 100 90 Annual bluegrass 80 80 Kentucky bluegrass 0 Sugarcane 0 Alfalfa 100 60 Pueraria javanica 80 Morningglory 60 100 Purslane 100 100 Ragweed 100 100 Peanut 70 70 Purple nutsedge 0 Yellow nutsedge 10 Compound 3 125 £4 22 1 Preemergence Bermudagrass 100 100 100 100 20 Broadleaf signalgrass 100 100 100 60 20 Guineagrass 100 100 100 100 30 Smooth crabgrass 100 100 100 100 50 Large crabgrass 100 100 100 95 60 Johnsongrass 100 100 100 85 30 Texas panicum 100 100 95 95 30 Itchgrass 100 100 100 95 60 Alfalfa 100 100 100 100 40 Pueraria javanica 100 100 90 80 50 Morningglory 100 100 80 90 40 Purslane 100 100 100 100 100 Field bindweed 100 100 100 100 100 Ragweed 100 100 100 100 0 Purple nutsedge 100 100 100 60 30 Yellow nutsedge 100 100 90 60 40 TABLE Pq Compound 3 125 £4 22 lfi 4 g/ha Postemergence Bermudagrass 100 100 95 80 50 Broadleaf signalgrass 100 100 100 50 20 Guineagrass 100 100 100 50 20 Smooth crabgrass 100 100 80 70 20 Large crabgrass 100 100 100 95 40 Johnsongrass 100 100 100 100 20 Texas panicum 100 100 95 80 20 Itchgrass 100 100 80 60 30 Kentucky bluegrass sod 85 60 30 30 20 Alfalfa 100 100 95 95 40 Morningglory 100 100 100 100 50 Purslane 100 100 100 100 100 Field bindweed 100 100 100 100 100 Ragweed 100 100 90 80 20 Purple nutsedge 100 100 60 40 30 Yellow nutsedge 100 100 90 60 20 TABLE Pr Compound 4 250 250 Zkfl Preemergence Postemergence Bermudagrass 90 0 Broadleaf signalgrass 100 20 Guineagrass 100 30 Smooth crabgrass 100 0 Large crabgrass 100 0 Johnsongrass 100 30 Texas panicum 100 10 Sandbur 0 70 Itchgrass 0 0 Goosegrass 100 50 Dallisgrass 100 80 Annual bluegrass 60 0 Kentucky bluegrass sod 0 Alfalfa 0 10 Pueraria javanica 30 Morningglory 0 40 Purslane 100 50 Ragweed 100 20 Peanut 20 20 Purple nutsedge 10 Yellow nutsedge 30 TEST Q Seeds of crabgrass (Digitaria spp.), barnyardgrass CEchinochloa crus-galli). giant foxtail (Setaria fjahfirj), wild oats (A vena fatua), cheatgrass (Bromus R calimisV velvetleaf (Abutilon theophrasti). morningglory (Ipomoea spp.), cocklebur sorghum, corn, soybean, sugarbeet, cotton, rice, wheat, barley, cassia and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crops and weed species were 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 were maintained in a greenhouse for sixteen days, after which all species were compared to controls and visually rated for response to treatment. The ratings, summarized in Tables Qa-Qg 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 B albinism 6Y = abscised buds or flowers TAELE Compound 1 2000 400 2000 400 g/h& Preemergence Postemergence Corn IOC 9H 9B 9B Soybean IOC IOC 10B 10B Cotton 10B 10B Sorghum IOC IOC 10B 10B Morningglory IOC IOC 10B 10B Crabgrass IOC IOC 10B 10B Rice IOC IOC 10B 10B Barnyardgrass IOC IOC 10B 10B Spring wheat IOC IOC 10B 10B Wild oats IOC IOC 10B 10B Nutsedge IOC IOC 10B 9B Cocklebur IOC IOC 10B 10B Cassia IOC IOC 10B 10B Cpmppv pd 1 5_Q 1Q g hfl Preemergence Postemergence Corn 4C.9H 3C.8H 9B 4B Soybean 2C,9G 9G 9B 9B Cotton IOC 3G 10B 10B Sorghum 9C 9C 8B 5B Velvetleaf IOC IOC 10B 9B Morningglory IOC 2C,8H 10B 9B Giant foxtail 10H 9H 9B 7B Crabgrass 10H 6B 5B Rice 9C 2C.3G 9B 6B Barnyardgrass 9H 9H 10B 3B Spring wheat 9C 2C 8B 5B Winter barley 9C 8C 9B 5B Sugarbeet 10G 8G 10B 9B Wild oats 8C 1C 8B 6B Nutsedge 7G 3G 8B 7B Cheatgrass 5G 0 7B 5B Cocklebur 8C 1H 7B 7B TABLED Com ound 3 400 400 glh& Preemergence Postemergence Corn 9H 8B Soybean 10H 10B Cotton 10B Sorghum IOC 10B Momingglory IOC 10B Crabgrass IOC 10B Rice IOC 10B Barnyardgrass IOC 10B Spring wheat IOC 9B Wild oats IOC 10B Nutsedge IOC 9B Cocklebur IOC 10B Cassia IOC 9B TABLE Qd Compound 3 400 fifi 1Ω 400 50 10 Preemergence Postemergence Corn 10H 4C.9H 3C.8H 10B 9B 7B Soybean 10E 2C.9G 8G 10B 9B 8B Cotton 10H 6H 2G 10B 10B 10B Sorghum 10H 9H 8H 10B 9B 7B Velvetleaf 10H 10H 10H 10B 10B 10B Morningglory 10H 9H 2C,8H 10B 10B 9B Giant foxtail 10H 10H 9H 10B 10B 9B Crabgrass 10E 10H 9H 10B 10B 7B Rice 10H 3C/7G 2C.7G 10B 9B 7B Barnyardgrass 10H 10H 5C.8H 10B 10B 8B Spring wheat 10H 2C.7H 3C.6G 10B 8B 6B Winter barley 10H 5C.9H 6C 10B 8B 6B Sugarbeet 10H 10H 7H 10B 10B 9B Wild oats 9H 3C.6H 2C 10B 9B 7B Nutsedge IOC - - 10B 9B 4B Cheatgrass 9H 5G 0 10B 9B 4B Cocklebur 10H 3C.6G 2C 10B 8B 7B TABLE Qe Compound 4 400 Postemergence Corn 8B 8B Soybean 9C 9B Cotton - 10B Sorghum IOC 9B Momingglory IOC 10B Crabgrass IOC 10B Rice IOC 10B Barnyardgrass IOC 10B Spring wheat IOC 9B Wild oats IOC 10B Nutsedge IOC 9B Cocklebur IOC 9B Cassia IOC 10B TABLE Qf Compound 4 £0 10 Preemergence Postemergence Corn 2C.7H 0 3B 3B Soybean 2C.8G 3G 5B 7B Cotton 2C,3G 0 10B 10B Sorghum 8C 3C 6B 4B Velvetleaf IOC IOC 10B 4B Morningglory 1C.3G 2C,4G 9B 5B Giant foxtail 8H 3C 7B 3B Crabgrass 10E 7G 6B 1C Rice 7C 0 8B 3B Barnyardgrass 9C 7C 8B 3B Spring wheat 4C.6G 2G 7B 3B Winter barley 8C 2C 5B 3B Sugarbeet 8G 4G 7B 3B Wild oats 3C.6G 2G 7B 3B Nutsedge 4C 0 6B IB Cheatgrass 5G 0 4B IB Cocklebur 0 0 6B 4B Compound 5 1Q g ha Preemergence Postemergence Corn 5G 3G 7B 3B Soybean 9G 0 9B 7B Cotton 3C.7G 1C 10B 9B Sorghum 3C.5G 0 9B 5B Velvetleaf IOC 9C 10B 10B Morningglory 9H 0 10B 9B Giant foxtail 9H 5H 9B 8B Crabgrass 8H 0 9B 6B Rice 3G 0 9B 6B Barnyardgrass 3C.9H 3C.8H 10B 7B Spring wheat 7C 2C 6B 4B Winter barley 3G 1C.5G 7B 4B Sugarbeet 9C 8H 9B 8B Wild oats 4C 0 10B 5B Nutsedge 3G - 5B 2B Cheatgrass 2G 0 7B 2B Cocklebur 6H 0 8B 7B TEST R Postemergence Three round pans (25 cm diameter by 12.5 cm deep) were filled with Sassafras sandy loam soil. One pan was planted with nutsedge (Cvper lepod (Cassia (Abutilon theophrasti). lambsquarters (Orvza eativa). and teaweed (Sida spinosa). The second pot was planted with green foxtail (Setaria viridis). cocklebur morningglory (Ipomoea hederacea). cott johnsongrass (|?fr bu halepense). barnyardgrass EchjppcM a SDiSz galli). corn (Zea mavs). soybean (Glycine max), and giant foxtail (Setaria faberi). The third pot was planted with wheat Tritiff P? flPFtiYVPA barley (flordeum vulgare). wild buckwheat olygpp^T" convolvulus), downy brome (Bromus tectorum). sugarbeet (Beta vulgaris), wild oat (Avena fatua), common chickweed (Stellaria media), blackgrass (Alopecurus mvosuroides). and rape (Brassica napus). The plants were 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) were filled with Sassafras sandy loam soil. One pan was planted with nutsedge tubers, crabgrass, sicklepod, jimsonweed, velvetleaf, lambsquarters, rice, and teaweed. The second pot was planted with green foxtail, cocklebur, morningglory, cotton, johnsongrass, barnyardgrass, corn, soybean, and giant foxtail. The third pot was planted with wheat, barley, wild buckwheat, downy brome, sugarbeet, wild oat, common chickweed, blackgrass, and rape. The three pans were sprayed preemergence with the chemicals dissolved in a non-phytotoxic solvent.

Treated plants and controls were maintained in the greenhouse for approximately 24 days, then all rated plants were compared to controls and visually rated for plant response.

Response ratings used in Test Q were 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 was conducted. The results are shown in Tables Ra through Re.

TABLEJk Compound 1 125 £2 IS 4 glh& Preemergence Spring wheat 30 0 0 0 Sugarbeet 100 100 100 70 Rape 100 100 60 30 Wild oats 100 60 30 0 Blackgrass 100 80 50 30 Rice 100 60 30 0 Lambsquarters 100 100 100 100 Wild buckwheat 100 100 100 100 Chickweed 100 80 50 30 Corn 0 0 0 0 Soybean 100 60 20 0 Cotton 70 40 20 0 Velvetleaf 100 100 70 50 Morningglory 100 100 60 30 Crabgrass 100 100 100 90 Giant foxtail 100 100 100 100 Bamyardgrass 100 100 50 30 Johnsongrass 100 100 60 30 Nutsedge 50 30 0 0 Green foxtail 100 100 100 70 Cocklebur 90 60 30 0 Teaweed 100 100 90 70 Cassia 100 100 70 30 Jimsonweed 100 100 100 90 Cheatgrass 90 60 30 0 TABLELEh Compound 1 Ι2£ 62. 16. 4 Sfh& Postemergence Spring wheat 90 80 40 30 Sugarbeet 100 100 90 60 Rape 100 100 80 30 Wild oats 90 90 60 20 Blackgrass 90 90 40 30 Lambsquarters 100 100 100 100 Wild buckwheat 100 100 100 90 Chickweed 100 100 50 30 Corn 70 50 40 0 Soybean 100 100 90 80 Cotton 100 100 100 100 Velvetleaf 100 100 100 100 Morningglory 100 100 80 80 Crabgrass 100 100 70 30 Giant foxtail 100 100 60 30 Barnyardgrass 100 100 60 50 Johnsongrass 100 90 30 20 Nutsedge 90 50 30 0 Green foxtail 100 90 60 30 Cocklebur 80 70 50 40 Teaweed 100 100 100 100 Cassia 100 100 100 50 Jimson eed 100 100 100 100 Rice 100 100 80 40 Cheatgrass 90 60 50 40 TABLE Rc £2 IS 4 1 g/ha Preemergence Spring wheat 30 0 0 0 Sugar beet 100 100 50 0 Rape 100 30 20 0 Wild oats 40 20 0 0 Blackgrass 70 60 0 0 Downy brome 50 30 0 0 Lambsquarters 100 100 90 80 Wild buckwheat 100 100 60 30 Chick weed 50 30 0 0 Corn 100 80 0 0 Soybean 80 70 40 20 Cotton 100 20 0 0 Velvetleaf 100 100 70 - Morningglory 90 50 40 30 Crabgrass 100 100 70 60 Giant foxtail 100 100 70 30 Bamyardgrass 100 100 100 30 Johnsongrass 100 100 70 50 Nutsedge 100 100 100 100 Green foxtail 100 100 80 0 Cocklebur 60 50 30 30 Teaweed 100 100 70 50 Cassia 100 50 30 - Jimsonweed 100 90 40 30 Rice 100 70 60 0 TABLE Rd Compound 3 §2 i£ 4 1 g ha Postemergence Spring wheat 80 20 0 0 Sugarbeet 100 100 50 50 Rape 100 100 50 30 Wild oats 60 0 0 0 Blackgrass 70 50 0 0 Downy brome 70 20 0 0 Lambsquarters 100 100 80 0 Wild buckwheat 100 100 30 30 Chickweed 30 0 0 0 Corn 20 20 0 0 Soybean 60 50 30 0 Cotton 100 100 80 30 Velvetleaf 100 70 60 30 Morningglory 80 80 50 0 Crabgrass 90 70 30 0 Giant foxtail 100 100 0 0 Bamyardgrass 100 100 20 0 Johnsongrass 100 100 0 0 Nutsedge 40 40 30 25 Green foxtail 80 50 0 0 Cocklebur 40 40 0 0 Teaweed 100 50 50 40 Cassia 70 50 30 0 Jimsonweed 100 100 80 40 Rice 85 70 20 10 TABLE Re Compound 4 250 £2 IS 250 £2 1£ Preemergence Postemergence Spring wheat 70 30 0 - 40 30 Sugarbeet 100 90 70 100 80 50 Rape 100 80 50 100 90 80 Wild oats 100 50 30 80 60 30 Blackgrass 100 70 30 100 80 40 Lambsquarters 100 100 100 100 100 90 Wild buckwheat 100 100 100 100 100 70 Chickweed 60 30 0 50 0 0 Corn 50 0 0 60 10 10 Soybean 100 60 30 90 80 50 Cotton 100 30 0 100 100 100 Velvetleaf 100 100 80 100 100 90 Momingglory 100 60 30 100 80 50 Crabgrass 100 100 90 100 80 70 Giant foxtail 100 100 70 90 80 60 Barnyardgrass 100 100 90 100 100 60 Johnsongrass 100 100 80 90 90 30 Nutsedge 60 30 0 100 30 0 Green foxtail 100 100 70 100 80 40 Cocklebur 70 30 0 70 60 50 Teaweed 100 90 60 100 80 80 Cassia 100 90 80 100 70 50 Jimsonweed 100 100 80 100 100 70 Rice 70 40 0 100 90 30 Cheatgrass 80 30 0 80 70 30 TEST S Seeds of spring wheat (Tri i?Vm fl fifrYVJPX winter wheat Q\ aesiivum), spring barley (H dfmp vulgare). winter barley (fi. yjilgare), sugar beet (Beta vulgaris), rape (Brassica nja jiS), wild oat (Avena fatttfl), downy brome (Bromus frft^rinnA cheatgrass (£. fificflhjma), blackgrass (Alopercurus mvosuroides)T annual bluegrass (Poa fifljmffl), green foxtail (Setaria yjridis), Italian ryegrass 'Τ-"1"1 nwltiflpnim), jointed goatgrass (Aegilops cvhndrica). Matricaria in dor a. Qfllinm spp., Russian thistle (Salsola kali), lambsquarters (Cb^pppod uro jbjjja), kochia (Kochia scoparia). black nightshade speedwell (Veronica persica). wild buckwheat spp.), Veronica hederaefolia and field pennycress (Thlapsi arvensis) were placed in 26 cm plastic pans containing pasteurized sandy loam soil.

Plantings were maintained in the greenhouse for 28 days at which time the postemergence treatments were applied using compounds formulated in a non-phytotoxic solvent. The preemergence portion of the test was seeded just before spraying. The postemergence treatments also contained wild oats and blackgrass at 1-leaf and 3-leaf growth stages. All treatments were held in the greenhouse for an additional 21 days at which time visual assessments of plant injury were made using a scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal injury and 100 indicates complete control. The variation in observed activity could be due to the fact that the tests were conducted at different times of the year or on different growth stages of plants. The results are shown in Tables Sa through Sf.

TABLE Sa 250 125 £4 22 1£ fi Preemergence Spring wheat 100 90 - 70 50 20 Winter wheat 90 70 70 70 50 10 Spring barley 80 80 70 50 30 20 Winter barley 90 90 40 30 10 0 Sugarbeet 100 100 100 100 100 100 Rape 90 90 80 80 10 10 Wild oats 100 90 70 60 30 10 Downy brome 90 70 50 50 20 10 Cheatgrass 90 70 70 30 10 0 Blackgrass 90 90 70 60 30 10 Annual bluegrass 100 100 100 80 70 20 Green foxtail 100 100 100 100 100 80 Italian ryegrass 100 100 90 90 70 60 Goatgrass 90 60 40 30 10 0 Matricaria indora 100 100 100 100 100 100 Galium 60 50 10 0 0 0 Russian thistle 100 100 100 100 90 70 Lambsquarters 100 100 100 100 90 70 Kochia 100 100 100 100 80 80 Black nightshade 100 100 100 100 100 100 Speedwell 100 100 100 100 90 70 Veronica hederaefolia 100 100 100 100 60 30 Wild buckwheat 100 100 100 100 100 100 Viola 100 100 100 100 100 60 Field pennycress 100 100 100 100 100 100 TABLE Sb ComDOund 3 250 125 £4 32 IS fi Postemergence Spring wheat 100 60 40 10 10 10 Winter wheat 70 70 20 10 10 10 Spring barley 60 30 10 10 10 10 Winter barley 100 70 20 20 10 10 Sugarbeet 100 100 80 70 50 30 Rape 100 80 70 70 70 60 Wild oats 1-leaf 100 70 70 50 20 10 3-leaf 70 30 10 10 10 10 Downy brome 30 10 10 0 0 0 Cheatgrass 50 30 10 0 0 0 Blackgrass 1-leaf 80 20 20 10 0 0 3-leaf 90 30 10 10 10 0 Annual bluegrass 40 20 10 0 0 0 Green foxtail 100 100 80 20 0 0 Italian ryegrass 100 80 60 10 10 0 Goatgrass 30 10 10 10 10 0 Matricaria indora 100 100 100 100 100 100 Galium 100 70 60 30 30 10 Russian thistle 100 100 100 100 80 60 Lambsquarters 100 100 100 90 90 20 Kochia 100 100 100 100 100 80 Black nightshade 100 100 100 100 100 100 Speedwell 100 100 100 40 40 10 Veronica hederaefolia 100 100 100 60 20 0 Wild buckwheat 100 100 100 100 80 10 Viola 100 100 100 100 100 100 Field pennycress 100 100 100 100 100 100 TABLE Sc Compound 3 250 125 £4 22 1£ £ Preemergence Spring wheat 100 95 95 70 65 35 Winter wheat 100 100 95 70 65 50 Spring barley 100 90 80 70 65 45 Winter barley 100 95 95 80 65 40 Sugarbeet 100 100 100 95 95 90 Rape 100 100 100 90 80 65 Wild oats 100 100 100 60 60 35 Downy brome 70 75 50 25 10 5 Cheatgrass 90 95 80 55 55 30 Black rass 100 100 90 60 55 30 Annual biuegrass 100 100 95 80 75 55 Green foxtail 100 100 100 100 100 95 Italian ryegrass 100 100 100 80 75 65 Go at grass 90 75 55 20 0 0 Matricaria indora 100 100 100 100 100 90 Galium 70 30 10 10 5 5 Russian thistle 100 100 65 65 40 35 Lambsquarters 100 100 100 100 100 85 Kochia 100 100 100 100 95 85 Black nightshade 100 100 100 100 100 100 Speedwell 100 100 100 95 80 65 Veronica hederaefolia 100 100 100 95 80 65 Wild buckwheat 100 100 100 100 100 80 Viola 100 100 100 100 95 90 Field pennycress 100 100 100 100 100 95 TABLE Sd ComDound 3 250 125 £4 22 1£ £ Postemergence Spring wheat 40 35 25 15 15 15 Winter wheat 70 60 50 30 15 15 Spring barley 80 90 75 40 30 20 Winter barley 60 55 40 20 10 10 Sugarbeet 100 100 100 100 85 75 Rape 100 100 95 80 75 55 WiJd oats 1-leaf 100 90 85 50 25 10 3-leaf 100 90 55 30 15 10 Downy brome 40 30 20 20 10 10 Cheatgrass 60 75 45 30 10 10 Blackgrass 1-leaf 100 100 45 20 15 10 3-leaf 60 20 10 10 10 10 Annual bluegrass 80 85 60 20 10 10 Green foxtail 100 100 100 100 100 100 Italian ryegrass 90 95 80 55 15 10 Goatgrass 50 75 45 25 15 10 Matricaria indora 100 100 100 100 65 40 Galium 70 75 50 40 30 10 Russian thistle 100 100 100 95 85 70 Lambsquarters 100 100 95 90 80 60 Kochia 100 100 100 100 90 75 Black nightshade 100 100 100 85 85 75 Speedwell 100 100 100 60 50 20 Veronica hederaefolia 100 85 65 30 10 0 Wild buckwheat 100 100 100 100 85 50 Viola 100 95 85 75 40 15 Field pennycress 100 100 85 85 65 30 TABLE Se 250 125 22 Ifi g ha Preemergence Spring wheat 90 90 80 70 50 Winter wheat 90 90 90 80 60 Spring barley 80 80 80 80 70 Winter barley 80 60 60 40 20 Sugarbeet 100 100 100 100 100 Rape 100 100 100 100 90 Wild oats 100 100 100 90 70 Downy brome 60 30 30 20 0 Cheatgrass 80 20 20 20 10 Blackgrass 100 90 90 90 80 Annual bluegrass 100 100 100 90 80 Green foxtail 100 100 100 100 100 Italian ryegrass 100 100 100 90 50 Goatgrass 30 30 20 20 0 Matricaria indora 100 100 100 100 100 Galium 80 70 70 60 40 Russian thistle 100 100 100 100 80 Lambsquarters 100 100 100 100 100 Kochia 100 100 100 100 100 Black nightshade 100 100 100 100 100 Speedwell 100 100 100 100 80 Veronica hederaefolia 100 100 80 80 60 Wild buckwheat 100 100 100 100 100 Viola 100 100 100 90 90 Field pennycress 100 100 100 100 100 TABLE Sf 250 125 £4 22 lfi g ha Postemergence Spring wheat 30 30 30 30 20 Winter wheat 70 50 40 40 20 Spring barley 80 60 60 50 30 Winter barley 80 50 40 40 20 Sugarbeet 100 100 100 90 60 Rape 100 100 90 90 40 Wild oats 1-leaf 100 100 50 50 30 3-leaf 100 100 40 20 0 Downy brome 30 30 30 20 20 Cheatgrass 100 90 70 50 20 Blackgrass 1-leaf 100 80 50 50 20 3-leaf 80 60 30 30 10 Annual bluegrass 100 90 70 30 20 Green foxtail 100 100 100 100 70 Italian ryegrass 100 100 100 80 20 Goatgrass 90 90 50 50 20 Matricaria indora 100 100 100 60 10 Galium 100 70 50 50 20 Russian thistle 100 100 100 100 40 Lambsquarters 100 100 100 70 20 Kochia 100 100 100 80 60 Black nightshade 100 100 100 100 70 Speedwell 100 100 100 90 20 Veronica hederaefolia 100 100 60 60 10 Wild buckwheat 100 100 100 100 30 Viola 100 100 100 100 0 Field pennycress 100 100 100 100 10 TEST U Plastic pots were partially filled with silt loam soil. The soil was then saturated with water. Japonica rice fOrvza sativa) seedlings at the 2.0 to 2.5 leaf stage; seeds of barnyardgrass fEchjn chlog crwff-gfl duck salad (Heteranthera limojga.), and umbrella sedge and tubers of arrowhead (Sagittaria spp.), and waterchestnut (Eleocharis spp.) were planted into this soil. Several days after planting, water levels were raised to 3 cm above the soil surface and maintained at this level throughout the test. Chemical treatments were formulated in a non-phytotoxic solvent and applied directly to the paddy water. Treated plants and untreated controls were maintained in a greenhouse for approximately 21 days, after which all treated plants were compared to untreated control and visually evaluated for injury. Plant response ratings, summarized in Table Ua, are reported on a zero to 10 scale where zero is no effect and 10 is complete control.

TABLE Ua 500 250 125 £4 32 g/ha Japonica rice 100 98 90 70 70 Bamyardgrass 100 100 100 80 90 Water chestnut 100 80 60 50 50 Arrowhead 100 100 100 60 20 Duck salad 100 100 100 100 100 Umbrella sedge 100 100 100 100 100 TEST V The Corn and Sorghum Herbicide Test included the following species in both the preemergence and postemergence evaluations: Category Γ.ηττ» ητι firi ltfifir flTPe Crops Corn Zea mavs Soybean Glycine max Sorghum Sorghum bjcolor Grasses Green foxtail Setaria viridis Giant foxtail Setaria faberii Johnsong ass SftTTghv""* halepense Barnyardgrass Echinochloa crus-galli Fall panicum Panicum dichotomiflorum Crabgrass Digitaria sanguinalis Nutsedge Cyperus ™tf nd"s Broadleaves Cocklebur Morningglory Ipomoea hederacea Velvetleaf Abutilon theophrasti Jimsonweed Ppt.nra ff†.rprnn i»m Lambsquarters Chenopodinm ^lhnm Pigweed Amaranthus retroflexus Smartweed Polygonum persicaris Postemergence Postemergence plantings were grown in Sassafras sandy loam soil. Corn and soybeans were grown in separate 25 cm diameter containers. Sorghum and the seven grass weed species were grown in two 18 cm diameter containers, 4 species per container. The seven broadleaf weed species were also grown in two 18 cm diameter containers, 4 species in one container, 3 species in the second container. One additional planting of com in an 18 cm diameter container was made. The soil surface of this additional container of com was covered with the absorbent, perlite, before spray treatment so that test chemicals would enter the plant only via the foliage. The plants were 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 were 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 were made the day of or the day before spraying the test chemicals dissolved in a non-phytotoxic solvent.

Treated plants and controls were maintained in thegreenhouse for 2 to 4 weeks. Visual ratings were made using a scale of 0 to 100 where 0 indicates no effect, and 100 indicates complete control. The results are shown in Tables Va and Vb.

TABLE Ya 22 1£ 4 2 2 p/ha Postemergence Com 50 30 10 0 0 0 Sorghum 100 100 20 0 0 0 Soybean 70 60 20 10 10 0 Green foxtail 60 40 30 0 0 0 Giant foxtail 90 60 30 0 0 0 Fall panicum 95 50 30 0 0 0 Crabgrass 50 20 0 0 0 0 Barnyardg ass 100 100 20 0 0 0 Johnsong ass 100 90 20 20 0 0 Velvetleaf 100 100 100 20 0 0 Cocklebur 50 50 50 20 0 0 Smartweed 100 100 40 0 0 0 Lambsquarters 100 95 50 50 30 20 Pigweed 100 60 0 0 0 0 Ivyleaf morningglory 90 20 50 30 0 0 Jimsonweed 100 100 70 100 50 50 Corn* 30 10 0 0 0 0 •soil covered with perilite at time of postemergence treatment TABLE Vb Compound 1 Preemergence Corn 70 65 50 Sorghum 100 70 50 Soybean 100 100 55 Green foxtail 100 100 100 Giant foxtail 100 100 100 Fall panicum 100 100 100 Crabgrass 100 100 100 Barnyardgrass 100 100 100 Johnsongrass 100 100 100 Nutsedge 65 55 25 Velvetleaf 100 100 85 Cocklebur 55 25 0 Smartweed 100 100 100 Lambsquarters 100 100 100 Pigweed 100 100 100 Ivyleaf morningglory 45 35 20 Jimsonweed 100 100 100 TEST W Sugarcane plants growing in 20.3 cm plastic pots were cut back to stimulate ratoon growth. At the early ratoon stage the pots were seeded with itchgrass (£. ma&mji i) and large crabgrass (D_. R»np na1ifi seeds.

The pots were sprayed with Compound 1 formulated in a non-phytotoxic spray solvent. The treatments were postemergence to the sugarcane and preemergence to the weed seeds. Plants were visually rated 65 DAT and compared with the appropriate controls. The injury rating scale used in Test G was also used here. The results are shown in Table W.

TAffLE W Compound 1 250 g ha Postemergence Sugarcane 0 Preemergence Itchgrass 100 Guineagrass 100 Large crabgrass 100 TE&LX 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. The injury rating scale used in Test W was also used here. The results are shown in Table X.

XABLELX Compound 1 252 125 £4 g/ha Over-the-tpp Banana 20* 0 0 Post-directed Banana 0 0 0 *main stem died but healthy side suckers developed.

I BA-8861-A

Claims (13)

CLAIMS What is claimed is:

1. A method for controlling weeds in plantation crops which comprises applying to the locus of the weeds a herbicidally effective amount of wherein R is isopropyl, allyl, propaxgyl or -CH(CH3)C=CH; X is CI or Br; Y is F or CI; I Z is H or can be taken together with R as -CH2CHCH3 such that the linking oxygen is attached to the methine carbon;

2. A method of Claim 1 which comprises applying to the locus of the weeds a herbicidally effective amount of a compound of Formula I wherein X is CI, Y is CI and Z is H.

3. A method of Claim 2 wherein the plantation crop is selected from citrus, sugarcane, coffee, banana, oil palm, rubber and loblolly pine.

4. A method of Claim 2 wherein the compound is 2-[2,4-dichloro-5- 2-propynyl)oxy]phenyll-5,6,7,8-tetrahydro-l,2,4-triazolo[4,3-a] pyridin-3(2H -one .

5. A method of Claim 4 wherein the plantation crop is citrus. ° 101047/2 95

6. A method of Claim 4 wherein the plantation crop is sugarcane.

7. A method of Claim 4 wherein the plantation crop is coffee.

8. A method of Claim 4 wherein the plantation crop is banana.

9. A method of Claim 4 wherein the plantation crop is oil palm.

10. A method of Claim 4 wherein the plantation crop is rubber.

11. A method of Claim 4 wherein the plantation crop is loblolly pine and the compound is applied preemergent.

12. A method of Claim 4 wherein the plantation crop is grapes.

13. A method of Claim 4 wherein the plantation crop is fruit trees. For the Applicants, DR. REINHOLD COHN AND PARTNERS By: