AU604355B2 - Herbicides for controlling crabgrass in turf - Google Patents

Description

4 COMMONWEALTH OF AUSTRALIA PATENTS ACT 1952-1969 Case: 09-21(2386)A AS 35 5 FORPj COMPLETE SPECIFICATION (Original) Application Number: Lodged: Class: Int. Class Complete specification Lodoed: Accepted: Published: 0riority: :Rnlatcl Arl-t: This document contains the amendments made under Section 49 and is correct for printing.

A n Bp p) .2 pp *i *4 PG..a oa me of AnDlicant.: L(iC3C2rL of 7pplicaznt: ixctua. Irn tor/s: Address for Servide: Complete Specification MONSANTO COMPANY 800 North Lindbergh Boulevard, St. Louis, Missouri 63167, United States of America.

LAWRENCE DOUGLAS BRIDGE; THOMAS BERNARD KLEVORN; SCOTT K. PARRISH; RANDY JOHN THOMPSON; and DANE R. WILLIAMSON.

E. F. WELLINGTON CO., Patent and Trade Mark Attorneys, 457 St. Kilda Road, Melbourne, 3004, Vic.

for the invention entitled: "HERBICIDES FOR TUTRF ,E9" r Cor4-o0 q c(cq4r ys5 IF 4v I P aI 4 The following.statement is a full description of this invention FR"> including the best method of performing it known to.me/us:

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1-1 0 t-- 09-21(2386)A c c c G CC C C C C CC C C C C C C a C C C C C r This invention relates to herbicides for use in turf grasses for selective preemergence and postemergence of crabgrass as well as preemergence control of other weed species. These herbicides contain a derivative of a pyridine-3,5-dicarboxylic acid.

Pyridine herbicides are known in the art.

Specifically, U. S. Patent No. 4,692,184 issued September 8, 1987 discloses derivatives of the type of the present invention. The disclosure of this U. S. Patent is hereby incorporated herein by reference.

Brief Description of the Invention It is an object of this invention to provide a herbicidal method and compositions for selectively controlling grassy weeds such as crabgrass (Digitaria spp), and goosegrass (Eleusine indica) preemergence, as well as to control crabgrass after it has become established, in a broad spectrum of turf grasses without substantial injury to the turf grass. Another object is to 20 provide a method of controlling some other turf weeds, including some broadleaf weeds, preemergence.

These objects are achieved by using the compound S,S-dimethyl-2- (difluoromethyl)-4-(2-methylpropyl)-6-trifluoromethyl-3,5-pyridinecarbodithioate, 25 or herbicidal compositions containing that compound as an active ingredient. The compositions may be liquid emulsifiable concentrates), solids granules) or mixed liquid and solid phases wettable powders, water dispersible granules or microencapsulations).

Detailed Description of the Invention The compound which is the active ingredient of this invention may be prepared as shown in Example 'arc

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li!i ril :i Yi: I f 09-21(2386)A 146 of U. S. Patent 4,692,184 which is specifically incorporated herein by reference.

Compositions containing the above compound may be liquids, solids, or mixed solid and liquid phases as has been stated above. Preparation of these compositions is well within the skill of the art.

Herbicidal compositions for practicing this invention, including concentrates which require dilution prior to application, may contain the active ingredient and an adjuvant in liquid or solid form. The compositions are prepared by admixing the active ingredient with an adjuvant including diluents, extenders, carriers and conditioning agents to provide compositions in the form of finely-divided particulate solids, granules, pellets, solutions, dispersions, microcapsules or emulsions. Thus, it is believed that the active ingredient could be used with an adjuvant such as a finely-divided solid, a liquid of organic origin, water, a wetting agent, a dispersing agent, an emulsifying agent or any suitable combination of these.

Suitable wetting agents are believed to o 0o include alkyl benzene and alkyl naphthalene sulfon- 0"o 0 ates, sulfated fatty alcohols, amines or acid amides, 0 0 oo long chain acid esters of sodium isothionate, esters 0 0 oo 25 of sodium sulfosuccinate, sulfated or sulfonated fatty 00 o 0o table oils, ditertiary acetylenic glycols, polyoxyethylene derivatives of alkylphenols (particularly Ii c isooctylphenol and nonylphenol) and polyoxyethylene derivatives of the mono-higher fatty acid esters of *0 hexitol anhydrides sorbitan) and polyoxyethylene derivatives of caster oil. Preferred dis- 4 c persants are methyl cellulose, polyoxyethylene/ polyoxypropylene block copolymers, polyvinyl alcohol, c, c 35 sodium lignin sulfonates, polymeric alkyl naphthalene C C r 09-21(2386)A sulfonates, sodium naphthalene sulfonate, and polymethylene bisnaphthalene sulfonate.

Wettable powders are water-dispersible compositions containing the active ingredient, an inert solid extender and one or more wetting and dispersing agents. The inert solid extenders are usually of mineral origin such as the natural clays, diatomaceous earth and synthetic minerals derived from H silica and the like. Examples of such extenders include kaolinites, bentonite, attapulgite clay and synthetic magnesium silicate. The wettable powders compositions of this invention usually contain from about 0.5 to 60 parts (preferably from 5-20 parts) of i: active ingredient, from about 0.25 to 25 parts (prei 15 ferably 1-15 parts) of wetting agent, from about 0.25 I to 25 parts (preferably 1.0-15 parts) of dispersant and from 5 to about 95 parts (preferably 5-50 parts) of inert solid extender, all parts being by weight of the total composition. Where required, from about 0.1 i i 20 to 2.0 parts of the solid inert extender can be i replaced by a corrosion inhibitor or anti-foaming 0 agent or both.

i C Other formulations include dust concentrates 2i i 5 comprising from 0.1 to 60% by weight of the active 25 ingredient on a suitable extender; these dusts may be c diluted for application at concentrations within the S° range of from about 0.1-10% by weight.

Aqueous suspensions or emulsions may be C, prepared by stirring a nonaqueous solution of the ot 30 water-insoluble active ingredient and an emulsification agent with water until uniform and then homogenizing to give stable emulsion of very finelydivided particles. The resulting concentrated aqueous suspension is characterized by its extremely small particle size, so that when diluted and sprayed, S* coverage is very uniform. Suitable concentrations of

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09-21(2386)A active ingredients in these formulations are from about 0.1-60%, preferably 5-50%, by weight of active ingredient, the upper limit being determined by the solubility limit of active ingredient in the solvent.

Concentrates are usually solutions of active ingredient in water-immiscible or partially waterimmiscible solvents'together with a surface active agent. Suitable solvents for the active ingredient of this invention include dimethylformamide, chlorinated solvents, dimethylsulfoxide, N-methyl-pyrrolidone, hydrocarbons and water-immiscible ethers, esters or ketones. However, other high strength liquid concentrates may be formulated by dissolving the active ingredient in a solvent then diluting, with kerosene, to spray concentration. The concentrate compositions herein generally contain from about 0.1 to 95 parts (preferably 5-60 parts) active ingredient, about 0.25 to 50 parts (preferably 1-25 parts) surface active agent and where required about 4 to 94 parts solvent, all parts being by weight based on the total weight of emulsifiable concentrate.

Granules are physically stable particulate compositions comprising active ingredient adhering to or distributed through a basic matrix of an inert, 25 finely-divided particulate extender. In order to aid leaching of the active ingredient from the particulate, a surface active agent such as those listed hereinbefore can be present in the composition.

Natural clays, pyrophyllites, illite, gypsum, sand, and vermiculite are examples of operable classes of particulate mineral extenders. The preferred extenders are the porous, absorptive, preformed particles such as preformed and screened particulate attapulgite or heat expanded, particulate vermiculite and the finely-divided clays such as kaolin clays, hydrated attapulgite or bentonitic clays. These extenders are C CO cc C Ct C Cc C

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-1 -"ii 09-21(2386)A sprayed or blended with the active ingredient to form the herbicidal granules. The granular compositions of this invention may contain from about 0.1 to about parts by weight of active ingredient per 100 parts by weight of clay and 0 to about 5 parts by weight of surface active agent per 100 parts by weight of particulate clay.

Microencapsulated formulations containing the compound of this invention are conveniently prepared using the methods disclosed in the U.S.

Patents 4,280,833 and 4,417,916, the disclosures of which are incorporated herein by reference.

The compositions of this invention can also contain other additaments, for example, fertilizers, other herbicides, pesticides, plant growth regulators, safeners and the like used as adjuvants or in combination with any of the above-described adjuvants.

Chemicals useful in combination with the active ingredient of this invention will be selected for the spectrum of weeds which they control and will quite often be broadleaf-specific herbicides such as 2,4oS (dichlorophenoxy)-acetic acid salts or esters, 2methoxy-3,6-dichlorobenzoic acid salts or esters, or o o like herbicides which are not phytotoxic to the turf 25 grass present.

o e° The compound of this invention may also be used in combination with other known crabgrass control agents, such as monosodium methanearsonate.

0I Preferably, the application of the active compound of 30 this invention is such as to provide the active ingre- ,CO dient at a rate of about 0.14 to 3,36 Kg/ha, such as from 0.42 to 1.12 Kg/ha, and particularly about 0.56 c to 0.84 Kg/ha.

Turf grasses in which the compostions of this invention may safely be used to control preemergent or established crabgrass include both cool-season grasses such as Kentucky bluegrass (Poa pratensis), 09-21(2386)A Tall fescue (Festuca arundinacea), creeping red fescue (Festuca rubra), fine fescue (Festuca ovina), Bentgrass (Agrostis palustris), and Perennial Ryegrass (Lolium perenne) and warm-season grasses such as St.

Augustine (Stenotaphrum secundatum), Bermuda (Cynodon dactylon), Centipedegrass (Eremochloa ophiuroides), Zoysiagrass (Zoysia japonica), Bahiagrass (Paspalum notatum), Kikuyugrass (Pennisetum clandestinum), and Carpetgrass (Axonopus affinis, Axonopus compressus).

Compositions according to this invention have been tested and found to be effective for control of crabgrass under a variety of climatic conditions in various locations around the United States, including St. Charles, Missouri; Detroit and Lansing, Michigan; Memphis and Cordova, Tennessee; Peoria, Illinois; Loxley, Alabama; Pensacola and Zellwood, Florida; and Cincinnati, Ohio.

Herbicidal Data The efficacy of compositions and method of this invention is shown in the following tables. As used in these tables, the following terms have the following meanings: Symbol Meaning DAT Days after treatment when the observation is made.

i Control Degree (percent) of control of Sthe indicated weed or turf h/A species.

Injury Degree (percent) of injury (or control) of the turf grass species present EC Emulsifiable concentrate G Granular composition ME Microencapsulated composition.

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09-21(2386)A In the following tables, the weed preemergence tests are presented first in Tables 1 through followed by the weed postemergence tests in Tables 6 through 8. In some tests, precent control of other weed or turf species are reported also. The application rate ("Rate" column) of active ingredient is shown in Kg/ha. In most instances readings are shown for each of three plots in each test where readings were available. Where no reading was made, a dash appears in the tables.

ij j jI s PREEMERGENCE CRABGRASS TESTS~ TABLE 1 Location: Turf Type:- Memphis, Tennessee Bermudagras s Formulation 3 lb/gal EC (0.36 Kg/L) Rate 0-42 0.56 Crabgrass Control 31DAT 68DAT 89DAT 110DAT -75 70 55 45 79 72 45 50 58 -80 75 66 -100 -60 82 45 90 80 76 100 100 100 100 100 30 45 100 97 89 -96 11,00 96 100 1.00 30 100 100 1.00 100 100 Go osegras s Control 89DAT 110DAT 65 0 74 70 0.84 73 G0 100 1.12 1.68 TABLE 1 (cont.) Crabgrass Control Coosegirass Control Formulation

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,4 lb/gal ME (0.48 Kg/L) Rate 2.24 0-42 0-56 0-84 1.12 31DAT 20 45 45 45 37 45 35 30 68DAT 100 100 100 83 100 100 84 100 100 95 100 100 100 90 100 100 8 9DAT 95 100 100 82 70 100 78 89 100 87 100 100 90 100 80 87 97 100 100 75 69 8 7 01 100 100 100 100 84 100 95 87 100 72 100 90 100 75 60 65 75 100 100 95 65 100 48 0 100 9b 100 63 110DAT 89DAT 110DAT 1.68 TABLE~ i (contL) Crabgrass Control 31DAT 68DAT 89DAT 110DAT Goosegrass Control 89DAT 110DAT Formulation Rate 4 lb/gal ME 48 Kg/L) 2 2410 J-00 100 95 100 100 100 100 100 100 TIABLE I (Qont.) Crabgrass Control 31DAT 68DAT 89DAT ilODAT Goosegrass Control 89DAT liODAT s Formulation 8 lb/gal EC (0.36 Kgr/L) c.

Rate 2-24 0 .42 0.56 loo 100 100o 100 100 100 100 100 100 1.00 100 100 100 100 100 1.00 7 5 90 100 90 80 96 90 100 100 92 100 100 98 '12 99 80 100 80 75 99 88 78 100 89 85 100 lOC 0 s0 100 100 930 100 1.12 1068 09-21(2386)A TABLE 2' Location: St. Charles, Missouri Turf Type: Kentucky Bluegrass Crabgrass Control 119 DAT Bluegrass In jury 119 DAT Formul ati on S lb/gal EC (0 3 6 Kg/2) Rate 0.28 0 .56 0.8 68 76 93 74 84 100 100 89 86 100 100 100 83 100 100 100 100 79 100

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0'.51,G 0.28 0.42 0.,56 0. 84 mppp- -3-09-21(2386)A, TABLE 2 (cont.) Crabgrass Control 119 DAT Bluegrass injury 119 DAT Formulation

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4 lb/gal ME (0.48 Kg/L) Rate 1 .12 0 .28 0.42 100 i00 100 86 100 78 58 100 100 100 100 100 100 100 98 0.56 0 .84 1. 12 -14- ~09 -21( 2386 A TABLE 3 ,Location: Cincinnati, Ohio Turf Type: Kentucky Bluegrass Crabgrass Control 87 DAT Bluegrass Inj ury 87 DAT Formulation 3 lb/gal EC (0.36 Kg/L) Rate 0.28 0.42 0.56 I 2 100 87 76 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 4 lb/galI ME (0.48 Kg//L) 0.28 0 .42 0,.56 0 .84 v L t lmmwl TABLE 3 (cont.) 09-21(2386)A Crabgrass Control 8 7 DAT Bluegrass Injury 87 DAT Formulation *4 lb/gal ME (0.48 Kg/L)

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Rate 1.12 0.28 0.42 100 100 100 100 93 100 100 100 100 100 100 100 100 100 100 0.56 0. 84 1.12 -7 -16- 09-21(2386)A TABLE 4 Location: Cordova, Tennessee Turf Type: Bermudagrass Crabgrass Control 70 DAT 90 DAT 110 DAT Formulation 3 lb/gal EC (0.36 Kg/L) Rate 0.42 0.56 0.84 1.12 1.66 77 75 80 96 95 100 100 100 100 100 100 100 87 100 87 83 100 100 100 100 100 100 100 69 683 72 79 100 73 86 60 100 100 100 100 100 100 100 79 100 65 89 82 100 100 100 95 100 100 38 78 100 88 68 100 100 100 100 100 100 83 100 78 84 72 87 84 100 100 100 100 ao 0 4 G 0.42 0.56, 0 .84 1 .12 -17- 17--09-21(2386)A TABLE 4 (cont.) Crabgrass Control 70 DAT 90 DAT 110 DAT Formulation 0. 5% G 4 lb/gal ME (0,.48 Kg/L) Rate 1.68 0.42 0.56 0.84 100 100 100 75 78 100 100 81 100 .100 100 83 100 100 100 100 100 100 100 72 74 100 100 85 65 95 83 100 100 85 100 100 100 100 100 100 98 83 62 87 74 62 82 82 76 100 99 100 1.12 1.6 8 I 7 -18- 09-21(2386 )A TABLE S Location: St. Charles, Missouri Turf Type: Kentucky Bluegrass Goosegrass Control 31 DAT 84 DAT Formulation 3 lb/gal EC (0.36 Kg/L) Rate 0.56 0.084 1.112 100 82 100 100 100 100 100 100 100 100 100 79 100 100 100 96 100 86 1.*68 -19- -19- 09-21 (2386)A Locationo Turf Type; POSTEMERGENCE TESTS TABLE 6 Cincinnati, Ohio Kentucky Bluegrass Crabgrass Control Rate 34 DAT 80 DAT Formulation 3 lb/gal EC (0.36 Kg/L) is 0.28 0.42 0. 56 0.84 1.1.2 89 95 100 95 89 95 Pi9 96 100 100 100 100 100 100 84 100 96 79 100 100 78 100 78 77 72 100 76 84 100 100 100 100 100 100 98 89 83 100 100 78 100 100 99 100 100 98 4 lb/gal ME (0.48 Kg/L) 0.28 0 .42

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F ormulation 4 lb/gal EC (0.48 Kg/L) 0 G TABLE 6 (cant.) Rate 1L.12 0 28 Crabgrass Control 34 DAT 80 DAT 98 100 100 100 100 100 100 96 7 0.42 0.56 100 100 89 100 100 100 100 100 100 100 100 100 92 100 100 100 100 100 100 100 0.84 1.12 -21- TABLE 7 Location: St. Charles, Missouri Turf Type: Kentucky Bluegrass 09-21(2386),A Formulation, 3 lb/gal EC (0.36 Kg/L) Rate 0.56 1.12 1.68 2.24 Crabgras s Control 24 DAT 63 56 54 62 68 74 53 s0 53 78 82 57

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00 0 0 1. 12 1.68 2 .24 TABLE 8 Location: Cordova, Tennessee Turf Type: Bermudagrass Crabgrass Control Lespedeza Control Formulation 3 lb/gal EC (0.36 Kg/L) 19 27 DAT DAT DAT 47 6V 27 DAT DAT DAT Rate 0.56 1.12 1.68 '16 '75 72 88 100 95 100 100 99 100 100 25S 45 '12 86 83 90 95 95 98 94 65 0 2,8 47

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30 1L00 30 100 100 100 90 J.00 0 67

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10 0 0 2.24 0. 5% G 0.56 rrl air.i~a-~r r- TABLE 8 (cont.) Crabgrass Control Lespedeza Control 19 27 Formulation

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Rate 1.12 47 67 27 DAT DAT DAT 1.68 2.24 DAT DAT 0 45 0 50 0 40 0 55 0 65 0 45 0 75 0 45 0 60 0 45 0 45 0 50 0 50 0 50 0 65 0 50 0 35

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55 95 83 70 80 87 85 55 85 70 89 89 75 90 89 85 68 75 78 78 100 90 100 100 100 100 40 78 75 90 100 92 95 98 75 85 68 90 78 92 99 89 88 60 65 65 80 87 47

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0 0 0 0 0 0 0 0 0 67

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4 lb/gal ME (0.48 Kg/L) 0.56 1.12 1.68 89 0 90 35 97 20 95 20 100 0 40 65 100 ji 1 TABLE 8 (cont.) Formulation 4 lb/gal ME (0.48 Kg/L) Rate 2.24 Crabgrass Control 19 27 47 67 DAT DAT DAT DAT DAT 0 65 85 100 99 0 65 78 100 95 Lespedeza Control 27 47 67 DAT DAT DAT 0 70 80 100 99 1- The matter con claims is to be read as pa the present invention.

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Claims (14)

1. A method of selectively controlling crabgrass in turf which comprises applying to the turf locus an effective amount of S,S-dimethyl-2-(difluoromethyl)-4- (2-methylpropyl).-6-(trifluoromethyl) dithioate.

2. A method according to Claim 1 wherein the active ingredient is applied at a rate of 0.14 to

3.36 Kg/ha. 3. A method according to Claim 1 or 2 wherein the composition is in the liquid phase or solid phase or mixed liquid and solid phases.

4. A method according to Claim 3 wherein the composition is a granular solid.

A method according to Claim 3 wherein the composition is an emulsifiable concentrate.

6. A method according to Claim 3 wherein the composition is microencapsulated.

7. A method according to any one of Claims 1 to 6 wherein the composition contains one or more additaments or adjuvants selected from surface active agents, fertilizers, plant growth regulators, safeners, other crabgrass control agents, pesticides or other herbicides non-phytotoxic to turf grass.

8. A composition for selectively controlling crabgrass in turf containing an adjuvant and an effective amount of S,S-dimethyl-2-(difluoromethyl)-4-(2-methyl- propyl)-6-(trifluoromethyl)-3,5-pyridinecarbodithioate as an active ingredient. r r I -1 L 27

9. A composition according to liquid phase or solid phase or mixed phases.

A composition according to granular solid.

11. A composition according to emulsifiable concentrate.

12. A composition according to microencapsulated. Claim 8 which is in the liquid and solid Claim 9 which is a Claim 9 which is an Claim 9 which is U F I

13. A composition according to any one of Claims 8 to 12 which contains the active ingredient in an amount from 0.1-60% by weight for application of the active ingredient at a rate of 0.14 to 3.36 Kg/ha.

14. A composition according to any one of Claims 8 to 13 which contains one or more additaments or adjuvants selected from rsurface active agents, fertili- zers, plant growth regulators, safeners, other crabgrass control agents, pesticides or other herbicides non- phytotoxic to turf grass. DATED this 23rd day of September, A.D. 1988 MONSANTO COMPANY, By its Patent Attorneys, E. F. WELLINGTON CO., By: BRUCE S. WELLINGTON rt