WO2008008933A2

WO2008008933A2 - Method of controlling weeds

Info

Publication number: WO2008008933A2
Application number: PCT/US2007/073429
Authority: WO
Inventors: James T. Bahr
Original assignee: FMC Corp
Current assignee: FMC Corp
Priority date: 2006-07-14
Filing date: 2007-07-13
Publication date: 2008-01-17
Anticipated expiration: 2009-01-14
Also published as: WO2008008933A3

Abstract

The present invention relates to a method for controlling weeds selected from dandelion, field bindweed, mayweed, burcucumber, common ragweed, hedge bindweed, buffalobur, giant ragweed, wild sunflower, field poppy, field violet and marestail, comprising applying an effective amount of a composition comprising 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)pyrimidinedione to a locus where control is needed or expected to be needed.

Description

METHOD OF CONTROLLING WEEDS

This application claims the benefit of U.S. Provisional Application No. 60/830,932, filed July 14, 2006.

FIELD OF THE INVENTION

The present invention relates generally to methods of controlling weeds. In particular, it pertains to a method useful for control of weeds selected from dandelion, field bindweed, mayweed, burcucumber, common ragweed, hedge bindweed, buffalobur, giant ragweed, wild sunflower, field poppy, field violet and marestail.

BACKGROUND OF THE INVENTION

Large-seeded and perennial broadleaf weeds are important weed pests that cause significant damage and crop yield loss if left untreated. Large-seeded and perennial broadleaf weeds include, for example, dandelion, field bindweed, mayweed, burcucumber, common ragweed, hedge bindweed, buffalobur, giant ragweed, wild sunflower, field poppy, field violet and marestail. Traditionally, methods to control large-seeded and perennial broadleaf weeds have included use of triazines, sulfonylrueas and hormonal herbicides (such as dicamba and 2,4-D). There are many problems with use of these traditional herbicides on large-seeded and perennial broadleaf weeds. Triazine herbicides have carryover and groundwater problems. Sulfonylureas have weed resistance problems and long-term adverse crop effects. Hormonal herbicides have drift or off-target problems along with limited application windows. Other classes of compounds, such as many PPO-inhibitor herbicides, have typically exhibited poor control of large-seeded and perennial broadleaf weeds at use rates which are safe for crops. It would be advantageous to develop a new method of controlling large-seeded and perennial broadleaf weeds.

Cycloimido-substituted benzofused heterocyclic compounds and methods of their use have been disclosed in United States Patent number 6,077,812, the disclosure of which is incorporated herein by reference.

SUMMARY OF THE INVENTION

In accordance with the present invention, it has now been found that a new method of controlling large-seeded and perennial broadleaf weeds solves the problems of traditional methods such as carryover, groundwater, weed resistance, long-term adverse crop effects, drift and limited application windows while exhibiting good to excellent control of large-seeded and perennial broadleaf weeds. Specifically, the present invention is a method for controlling weeds selected from dandelion, field bindweed, mayweed, burcucumber, common ragweed, hedge bindweed, buffalobur, giant ragweed, wild sunflower, field poppy, field violet and marestail, comprising applying an effective amount of a composition comprising 3- (4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l-methyl-6-trifluoromethyl- 2,4(lH,3H)pyrimidinedione to a locus where control is needed or expected to be needed. Other aspects of the present invention will also be apparent.

DETAILED DESCRIPTION OF THE INVENTION

It has now been unexpectedly found that a method for controlling weeds selected from dandelion (Taraxacum officinale), field bindweed (Convolvulus arvensis), mayweed (Anthemis cotula), burcucumber (Sicyos angulatus), common ragweed (Ambrosia artemisifolia), hedge bindweed (Convolvulus sepium), buffalobur (Solanum rostratum), giant ragweed (Ambrosia trifida), wild sunflower (Helianthus annus), field poppy (Papaver dubium), field violet (Viola arvensis) and marestail (Hippuris vulgaris), comprises applying an effective amount of a composition comprising 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)- l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione to a locus where control is needed or expected to be needed, results in effective control of these large-seeded and perennial broadleaf weeds. It has also been unexpectedly found that control of these weeds is accomplished at use rates which exhibit good tolerance by crops such as corn and wheat.

The 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l-methyl-6- trifluoromethyl-2,4(lH,3H)pyrimidinedione can be present in a concentration of from 0.001% by weight to 5.0% by weight based upon the total weight of all components in the composition. Preferably, the 3-(4-chloro-6-fluoro-2- trifluoromethylbenzimidazol-7-yl)- 1 -methyl-6-trifluoromethyl- 2,4(lH,3H)pyrimidinedione is present in a concentration of from 0.0016% by weight to 0.15% by weight based upon the total weight of all components in the composition. More preferably, the 3-(4-chloro-6-fluoro-2- trifluoromethylbenzimidazol-7-yl)- 1 -methyl-6-trifluoromethyl- 2,4(lH,3H)pyrimidinedione is present in a concentration of from 0.0048% by weight to 0.08% by weight based upon the total weight of all components in the composition.

The composition may further comprise a second herbicide providing the second herbicide does not adversely affect the herbicidal action of 3-(4-chloro-6- fluoro-2-trifluoromethylbenzimidazol-7-yl)-l-methyl-6-trifluoromethyl- 2,4(lH,3H)pyrimidinedione. For example it can sometimes be useful to include additional herbicides to extend the range of activity in order to control a wider spectrum of weeds. The second herbicide can be N-(phosphonomethyl)glycines such as glyphosate; aryloxyalkanoic acids such as 2,4-D, MCPA, and MCPP; ureas such as isoproturon; imidazolinones such as imazapyr, imazamethabenz-methyl, imazethapyr, and imazaquin; hydroxybenzonitriles such as ioxynil and bromoxynil; sulfonylureas such as chlorimuron, chlorsulfuron, bensulfuron, pyrazosulfuron, thifensulfuron, and triasulfuron; 2-(4-aryloxyphenoxy)alkanoic acids such as fenoxaprop, fluazifop, quizalofop, and diclofop; benzothiadiazinones such as bentazone; 2-chloroacetanilides such as butachlor, metolachlor, acetochlor, and dimethenamide; arenecarboxylic acids such as dicamba; pyridyloxyacetic acids such as fluroxypyr; aryl triazolinones such as sulfentrazone and carfentrazone-ethyl; isoxazolidinones such as clomazone; sulfonanilides such as florasulam; anilides such as diflufenican; dinitroanilines such as pendimethalin; benzoylcyclohexanediones such as mesotrione; picolinic acids such as clopyralid; cyclohexene oximes such as tralkoxydim; and triazolones such as flucarbazone. One skilled in the art will, or course, recognize that the formulation and mode of application of a toxicant may affect the activity of the material in a given application. Thus, for use in the control of weeds, the herbicide finding utility in the present invention may be formulated as granules of relatively large particle size, as water-soluble or water-dispersible granules, as powdery dusts, as wettable powders, as emulsifiable concentrates, as solutions, or as any of several other known types of formulations, depending on the desired mode of application. It is to be understood that the amounts specified in this specification are intended to be approximate only, as if the word "about" were placed in front of the amounts specified. These herbicidal compositions may be applied either as water-diluted sprays, or dusts, or granules to the areas in which suppression of vegetation is desired. These formulations may contain as little as 0.1%, 0.2% or 0.5% to as much as 95% or more by weight of active ingredient. Dusts are free flowing admixtures of the active ingredient with finely divided solids such as talc, natural clays, kieselguhr, flours such as walnut shell and cottonseed flours, and other organic and inorganic solids which act as dispersants and carriers for the toxicant; these finely divided solids have an average particle size of less than about 50 microns. A typical dust formulation useful herein is one containing 1.0 part or less of the herbicidal compound and 99.0 parts of talc.

Wettable powders are in the form of finely divided particles, which disperse readily in water or other dispersant. The wettable powder is ultimately applied either as a dry dust or as an emulsion in water or other liquid. Typical carriers for wettable powders include Fuller's earth, kaolin clays, silicas, and other highly absorbent, readily wet inorganic diluents. Wettable powders normally are prepared to contain about 5 - 80% of active ingredient, depending on the absorbency of the carrier, and usually also contain a small amount of a wetting, dispersing or emulsifying agent to facilitate dispersion. For example, a useful wettable powder formulation contains 80.0 parts of the herbicidal compound, 17.9 parts of Palmetto clay, and 1.0 part of sodium lignosulfonate and 0.3 part of sulfonated aliphatic polyester as wetting agents.

Other useful formulations for herbicidal applications are emulsifiable concentrates (ECs) which are homogeneous liquid compositions dispersible in water or other dispersant, and may consist entirely of the herbicidal compound and a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthas, isophorone, or other non-volatile organic solvents. For herbicidal application these concentrates are dispersed in water or other liquid carrier and normally applied as a spray to the area to be treated. The percentage by weight of the essential active ingredient may vary according to the manner in which the composition is to be applied, but in general comprises 0.25 to 95% of active ingredient by weight of the herbicidal composition.

Suspension concentrate formulations may also be employed. These are similar to ECs, except that the herbicidal compounds are suspended in a liquid carrier, generally water. Suspension concentrates, like ECs, may include a small amount of a surfactant, and will typically contain the herbicidal compounds in the range of 0.5 to 95%, frequently from 10 to 50%, by weight of the total composition. For example, a useful suspension concentrate formulation contains 22.0 parts of the herbicidal compounds, 2.6 parts of ethoxylated/propoxylated block copolymer surfactant, 0.4 part phosphate ester surfactant, 0.8 part thickening agent, 6.0 parts antifreeze agent, 0.1 antifoam agent, 0.05 part anti-bactericide and 44.0 parts distilled water. For herbicidal application, suspension concentrates may be diluted in water or other liquid vehicle, and are normally applied as a spray to the area to be treated.

Typical wetting, dispersing or emulsifying agents used in certain formulations include, but are not limited to, the alkyl and alkylaryl sulfonates and sulfates and their sodium salts; alkylaryl polyether alcohols; sulfated higher alcohols; polyethylene oxides; sulfonated animal and vegetable oils; sulfonated petroleum oils; fatty acid esters of polyhydric alcohols and the ethylene oxide addition products of such esters; and the addition product of long chain mercaptans and ethylene oxide. Many other types of useful surface - active agents are available in commerce. Surface-active agents, when used, normally comprise 1 to 15% by weight of the composition. Still other useful formulations for herbicidal applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene, or other organic solvents. Granular formulations, wherein the toxicant is carried on relative coarse particles, are of particular utility for aerial distribution or for penetration of a cover canopy. Pressurized sprays, typically aerosols wherein the active ingredient is dispersed in finely divided form as a result of vaporization of a low-boiling dispersant solvent carrier may also be used. Water-soluble or water-dispersible granules are free-flowing, non-dusty, and readily water-soluble or water-miscible. In use by the farmer on the field, the granular formulations, emulsifiable concentrates, suspension concentrates, solutions, etc., may be diluted with water to give a concentration of active ingredient in the range of 0.001% by weight to 5.0% by weight. In the context of the present invention, the term "herbicide" refers to the active chemical compound or ingredient, which kills or controls weeds. The term "liquid herbicide" refers to a formulation of an herbicide where the formulation can be dispensed in an aqueous medium prior to its use. The term "locus" refers to any locations where control of dandelion, field bindweed, mayweed, burcucumber, common ragweed, hedge bindweed, buffalobur, giant ragweed, wild sunflower, field poppy, field violet or marestail is needed or expected to be needed. The term "controlling" refers to the killing of, or minimizing the amount of weeds to a point where they no longer pose a threat to desired vegetation. The term "% by weight" refers to the weight of the herbicide or other specified component as a percent of the total weight of the composition (e.g. including the aqueous medium, other herbicides, surfactants, wetting agents, freeze/thaw agents and combinations thereof).

The term "3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l- methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione" refers to a compound of Formula I:

Formula I. The term "mesotrione" refers to (2-[4-(methylsulfonyl)-2-nitrobenzoyl]-l,3- cyclohexanedione). The term "carfentrazone-ethyl" refers to ethyl 2-chloro-3-[2- chloro-5 -(4-difluoromethyl-4,5 -dihydro-3 -methyl-5-oxo- IH-1 ,2,4-triazlo- 1 -yl)-4- fluorophenyl]propionate. The term "dicamba" refers to 3,6-dichloro-2- methoxybenzoic acid or an agriculturally acceptable salt of 3,6-dichloro-2- methoxybenzoic acid. The term "atrazine" refers to 6-chloro-N-ethyl-N'-(l- methylethyl)-l,3,5-triazine-2,4-diamine. The term "pyridate" refers to O-(6-chloro- 3-phenyl-4-pyridazinyl) S-octyl carbonothioate. The modifier "about" is used herein to indicate that certain preferred ranges are not fixedly determined. The meaning will often be apparent to one of ordinary skill. Where guidance from the experience of those of ordinary skill is lacking, guidance from the context is lacking, and where a more specific rule is not recited below, the "about" range shall be not more than 10% of the absolute value of an end point or 10% of the range recited, whichever is less.

The following examples further illustrate the present invention, but, of course, should not be construed as in any way limiting its scope. The desired concentration of the active ingredients was achieved by diluting, with water, a soluble dust formulation (DF) or a suspension concentrate formulation (SC) of 3-(4- chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l-methyl-6-trifluoromethyl- 2,4(lH,3H)pyrimidinedione. Test compositions also contained conventional surfactants such as, but not limited to, crop oil concentrate.

EXAMPLE 1

Herbicidal evaluation of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)- l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione on Giant Ragweed

The compositions of the present invention were tested for herbicidal efficacy in the following manner:

Test compositions of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7- yl)-l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione (using 25 DF) were prepared in a spray tank that provided the appropriate application rate of 3-(4- chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l-methyl-6-trifluoromethyl- 2,4(lH,3H)pyrimidinedione.

The application of the test composition was performed with pressurized back-pack sprayers, calibrated to spray between 10 and 20 gallons per acre.

The experimental design used randomized plots with one post-emergent treatment and four to eight replications per test trial. The size of each experimental plot was typically 6 feet by 20 feet.

The weeds were evaluated and averaged in each experimental plot at 21 days after treatment (DAT) of each test composition.

The results, shown as an average of 4-8 replications, were compared with results observed in plots treated with commercial formulations of carfentrazone- ethyl (AIM^® EW Herbicide from FMC Corporation), a mixture of atrazine and dicamba (Marksman^® Herbicide from BASF Corporation) and mesotrione (Callisto® Herbicide from Syngenta Crop Protection, Inc.) in the same trials. The results and comparison are in Table 1 below.

TABLE 1

Herbicidal Activity of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l- methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione when applied to Giant

Ragweed, 21 DAT

Treatment Rate of % Control Appln (Ib AI per Acre)

A 0008 76 0 016 84

0 024 90

0 032 91

0 048 94

AIM 0 008 52

Marksman 1 0 99

Callisto 094 86

A = 3-(4-chloro-6-fluoro-2-tnfluoromethylbenzimidazol-7-yl^

EXAMPLE 2 Herbicidal evaluation of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)- l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione on Common Ragweed

The compositions of the present invention were tested for herbicidal efficacy in the following manner: Test compositions of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7- yl)-l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione (using 25 DF) were prepared in a spray tank that provided the appropriate application rate of 3-(4- chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l-methyl-6-trifluoromethyl- 2,4( 1 H,3H)pyrimidinedione. The application of the test composition was performed with pressurized back-pack sprayers, calibrated to spray between 10 and 20 gallons per acre. The experimental design used randomized plots with one post-emergent treatment and five to ten replications per test trial. The size of each experimental plot was typically 6 feet by 20 feet.

The results, shown as an average of 5-10 replications, were compared with results observed in plots treated with commercial formulations of carfentrazone- ethyl (AIM^® EW Herbicide from FMC Corporation) and a mixture of atrazine and dicamba (Marksman^® Herbicide from BASF Corporation) in the same trials. The results and comparison are in Table 2 below.

TABLE 2 Herbicidal Activity of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l- methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione when applied to Common Ragweed, 21 DAT

Treatment Rate of % Control Appln (Ib AI per Acre)

A 0 008 81 0 016 88

0 024 91

0 032 93

0 048 94

AIM 0 008 68

Marksman^® 1 0 77

A = 3-(4-chloro-6-fluoro-2-tnfluoromethylbenzimidazol-7-yl^

EXAMPLE 3 Herbicidal evaluation of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)- l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione on Common Sunflower

The compositions of the present invention were tested for herbicidal efficacy in the following manner: Test compositions of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7- yl)-l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione (using 25 DF) were prepared in a spray tank that provided the appropriate application rate of 3 -(4- chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l-methyl-6-trifluoromethyl- 2,4( 1 H,3H)pyrimidinedione.

The application of the test composition was performed with pressurized back-pack sprayers, calibrated to spray between 10 and 20 gallons per acre. The experimental design used randomized plots with one post-emergent treatment and two to four replications per test trial. The size of each experimental plot was typically 6 feet by 20 feet.

The weeds were evaluated and averaged in each experimental plot at 15 days after treatment (DAT) of each test composition. The results, shown as an average of 2-4 replications, were compared with results observed in plots treated with commercial formulations of carfentrazone- ethyl(AIM^® EW Herbicide from FMC Corporation), a mixture of atrazine and dicamba (Marksman^® Herbicide from BASF Corporation) in the same trials. The results and comparison are in Table 3 below.

TABLE 3

Herbicidal Activity of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l- methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione when applied to Common

Sunflower, 15 DAT

Treatment Rate of % Control

Appln

(Ib AI per

Acre)

A 0008 68

0 016 84

0 024 89

0 032 94

0 048 97

AIM 0 008 49

Marksman^® 1 0 96

A = 3-(4-chloro-6-fluoro-2-tπfluoromethylbenzimidazol-7-yl)-l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione

EXAMPLE 4

Herbicidal evaluation of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)- l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione on Burcucumber

The compositions of the present invention were tested for herbicidal efficacy in the following manner: Test compositions of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7- yl)-l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione (using a 25 DF) were prepared in a spray tank that provided the appropriate application rate of 3-(4- chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l-methyl-6-trifluoromethyl- 2,4(lH,3H)pyrimidinedione.

The experimental design used randomized plots with one post-emergent treatment and four replications per test trial. The size of each experimental plot was typically 6 feet by 20 feet.

The weeds were evaluated and averaged in each experimental plot at 14 days after treatment (DAT) of each test composition.

The results, shown as a mean of 4 replications, are in Table 4 below.

TABLE 4

Herbicidal Activity of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l- methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione when applied to

Burcucumber, 14 DAT

Treatment Rate of % Control

Appln (Ib AI per Acre)

A 0008 95

0 016 91

0 020 89

A = 3-(4-chloro-6-fluoro-2-tnfluoromethylbenzimidazol-7-yl^

EXAMPLE 5 Herbicidal evaluation of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)- l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione on Common Mares-Tail

The compositions of the present invention were tested for herbicidal efficacy in the following manner: Test compositions of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7- yl)-l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione (using a 5 SC) were prepared in a spray tank that provided the appropriate application rate of 3-(4- chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l-methyl-6-trifluoromethyl- 2,4( 1 H,3H)pyrimidinedione.

The experimental design used randomized plots with one post-emergent treatment and two to four replications per test trial. The size of each experimental plot was typically 6 feet by 20 feet.

The weeds were evaluated and averaged in each experimental plot at 13-25 days after treatment (DAT) of each test composition.

The results, shown as a mean of 2-4 replications, are in Table 5 below.

TABLE 5

Mares-Tail

Treatment Rate of % Control

Appln (Ib AI per Acre)

A 0008 91

0 015 87

0 024 99

EXAMPLE 6

Herbicidal evaluation of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)- l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione on Field Bindweed

Test compositions of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7- yl)-l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione (using a 25 DF) were prepared in a spray tank that provided the appropriate application rate of 3-(4- chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l-methyl-6-trifluoromethyl- 2,4( 1 H,3H)pyrimidinedione. The application of the test composition was performed with pressurized back-pack sprayers, calibrated to spray between 10 and 20 gallons per acre.

The experimental design used randomized plots with one post-emergent treatment and two replications per test trial. The size of each experimental plot was typically 6 feet by 20 feet.

The results, shown as an average of 2 replications, were compared with results observed in plots treated with a commercial formulation of dicamba- dimethylammonium salt (Banvel^® Herbicide available from Novartis Corporation) in the same trials. The results and comparison are in Table 6 below.

TABLE 6

Herbicidal Activity of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l- methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione when applied to Field

Bindweed, 21 DAT

Treatment Rate of % Control Appln (Ib AI per Acre)

A 0008 80 0 016 97

0 024 100

0 032 100

Banvel 0 188 88

A = 3-(4-chloro-6-fluoro-2-tnfluoromethylbenzimidazol-7-yl^

EXAMPLE 7

Herbicidal evaluation of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)- l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione on Buffalobur

Test compositions of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7- yl)-l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione (using a 5 SC) were prepared in a spray tank that provided the appropriate application rate of 3-(4- chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l-methyl-6-trifluoromethyl- 2,4( 1 H,3H)pyrimidinedione.

The weeds were evaluated and averaged in each experimental plot at 13-25 days after treatment (DAT) of each test composition. The results, shown as a mean of 2-4 replications, are in Table 7 below.

TABLE 7

Herbicidal Activity of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l- methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione when applied to Buffalobur

Treatment Rate of % Control

Appln (Ib AI per Acre)

A 0008 72

0 015 92

0 024 97

EXAMPLE 8

Herbicidal evaluation of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)- l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione on Mayweed

Test compositions of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7- yl)-l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione (using a 50 g/1 SC) were prepared in a spray tank that provided the appropriate application rate of 3-(4- chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l-methyl-6-trifluoromethyl- 2,4(lH,3H)pyrimidinedione.

The application of the test composition was performed with pressurized back-pack sprayers, calibrated to spray between 10 and 20 gallons per acre. The experimental design used randomized plots with one post-emergent treatment and six replications per test trial. The size of each experimental plot was typically 6 feet by 20 feet.

The weeds were evaluated and averaged in each experimental plot at 12-18 days after treatment (DAT) of each test composition.

The results, shown as a mean of 6 replications, are in Table 8 below. Both scentless and scented Mayweed were tested and both are included in the mean.

TABLE 8 Herbicidal Activity of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l- methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione when applied to Mayweed

Treatment Rate of % Control

Appln (Ib AI per Acre)

A 0017 79

0 034 91

0 051 97

0 068 98

EXAMPLE 9

Herbicidal evaluation of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)- l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione on Hedge Bindweed

Test compositions of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7- yl)-l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione (using a 200 g/1 SC) were prepared in a spray tank that provided the appropriate application rate of 3-(4- chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l-methyl-6-trifluoromethyl- 2,4( 1 H,3H)pyrimidinedione.

The application of the test composition was performed with pressurized back-pack sprayers, calibrated to spray between 10 and 20 gallons per acre. The experimental design used randomized plots with one post-emergent treatment and three replications per test trial. The size of each experimental plot was typically 6 feet by 20 feet.

The results, shown as an average of 3 replications, were compared with results observed in plots treated with a commercial formulation of pyridate (Tough 450 EC Herbicide available from Bayer Crop Science) in the same trials. The results and comparison are in Table 9 below.

TABLE 9

Herbicidal Activity of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l- methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione when applied to Hedge

Bindweed

Treatment Rate of % Control

Appln (Ib AI per Acre)

A 0026 99

0 038 97

0 051 99 pyπdate 0386 50

EXAMPLE 10

Herbicidal evaluation of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)- l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione on Dandelion

Test compositions of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7- yl)-l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione (using a 25 DF) were prepared in a spray tank that provided the appropriate application rate of 3-(4- chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l-methyl-6-trifluoromethyl- 2,4(lH,3H)pyrimidinedione. The application of the test composition was performed with pressurized back-pack sprayers, calibrated to spray between 10 and 20 gallons per acre.

The experimental design used randomized plots with one post-emergent treatment and three replications per test trial. The size of each experimental plot was typically 6 feet by 20 feet.

The weeds were evaluated and averaged in each experimental plot at 17 days after treatment (DAT) of each test composition.

The results, shown as an average of 3 replications, are in Table 10 below.

TABLE 10

Herbicidal Activity of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l- methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione when applied to Dandelion,

17 DAT

Treatment Rate of % Control Appln (Ib AI per Acre)

A 0008 37 0 016 47

0 031 70

0 063 90

0 125 100

A = 3-(4-chloro-6-fluoro-2-tnfluoromethylbenzimidazol-7-yl^

EXAMPLE 11 Herbicidal evaluation of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)- l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione on Field Poppy

The compositions of the present invention were tested for herbicidal efficacy in the following manner: Test compositions of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7- yl)-l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione (using a 240 g/1 SC) were prepared in a spray tank that provided the appropriate application rate of 3-(4- chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l-methyl-6-trifluoromethyl- 2,4( 1 H,3H)pyrimidinedione. The application of the test composition was performed with pressurized back-pack sprayers, calibrated to spray between 10 and 20 gallons per acre.

The weeds were evaluated and averaged in each experimental plot at 13-16 days after treatment (DAT) of each test composition.

The results, shown as an average of 3 replications, are in Table 11 below.

TABLE 11

Herbicidal Activity of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l- methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione when applied to Field Poppy

Treatment Rate of % Control

Appln (Ib AI per Acre)

A 0026 68

0 034 72 A = 3-(4-chloro-6-fluoro-2-tπfluoromethylbenzimidazol-7-yl)-l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione

EXAMPLE 12

Herbicidal evaluation of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)- l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione on Field Violet

Test compositions of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7- yl)-l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione (using a 240 g/1 SC) were prepared in a spray tank that provided the appropriate application rate of 3-(4- chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l-methyl-6-trifluoromethyl- 2,4( 1 H,3H)pyrimidinedione.

The application of the test composition was performed with pressurized back-pack sprayers, calibrated to spray between 10 and 20 gallons per acre. The experimental design used randomized plots with one post-emergent treatment and five replications per test trial. The size of each experimental plot was typically 6 feet by 20 feet.

The results, shown as an average of 5 replications, are in Table 12 below.

TABLE 12

Herbicidal Activity of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l- methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione when applied to Field Violets

Treatment Rate of % Control

Appln (Ib AI per Acre)

A 0026 91

0 034 94

EXAMPLE 13

Test compositions of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7- yl)-l-methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione (using a 25 DF) were prepared in a spray tank that provided the appropriate application rate of 3-(4- chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l-methyl-6-trifluoromethyl- 2,4( 1 H,3H)pyrimidinedione.

The application of the test composition was performed with pressurized back-pack sprayers, calibrated to spray between 10 and 20 gallons per acre. The experimental design used randomized plots with one pre-emergent treatment either the day of planting or the day after planting and three replications per test trial. The size of each experimental plot was typically 6 feet by 20 feet. The weeds were evaluated and averaged in each experimental plot at 14 days after treatment (DAT) of each test composition.

The results, shown as an average of 3 replications, are in Table 13 below.

TABLE 13

Herbicidal Activity of 3-(4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l- methyl-6-trifluoromethyl-2,4(lH,3H)pyrimidinedione when applied to Pre-

Emergent Dandelion, 14 DAT

Treatment Rate of % Control

Appln (Ib AI per Acre)

A 0063 90

0 125 95

0 250 100

Those of ordinary skill in the art will appreciate that variations of the invention may be used and that it is intended that the invention may be practiced otherwise than as specifically described herein. Accordingly, this invention includes all modifications encompassed within the spirit and scope of the invention as defined by the following claims.

Claims

What is claimed is:

1. A method for controlling weeds selected from the group consisting of dandelion, field bindweed, mayweed, burcucumber, common ragweed, hedge bindweed, buffalobur, giant ragweed, wild sunflower, field poppy, field violet and marestail, comprising applying a composition comprising 3-(4-chloro-6-fluoro-2- trifluoromethylbenzimidazol-7-yl)- 1 -methyl-6-trifluoromethyl- 2,4(lH,3H)pyrimidinedione to a locus where control is needed or expected to be needed.

2. The method according to claim 1, wherein the 3-(4-chloro-6-fluoro-2- trifluoromethylbenzimidazol-7-yl)- 1 -methyl-6-trifluoromethyl- 2,4(lH,3H)pyrimidinedione is present in a concentration of from 0.001% by weight to 5.0% by weight based upon the total weight of all components in the composition.

3. The method according to claim 2, wherein the 3-(4-chloro-6-fluoro-2- trifluoromethylbenzimidazol-7-yl)- 1 -methyl-6-trifluoromethyl- 2,4(lH,3H)pyrimidinedione is present in a concentration of from 0.0016% by weight to 0.15% by weight based upon the total weight of all components in the composition.

4. The method according to claim 3, wherein the 3-(4-chloro-6-fluoro-2- trifluoromethylbenzimidazol-7-yl)- 1 -methyl-6-trifluoromethyl- 2,4(lH,3H)pyrimidinedione is present in a concentration of from 0.0048% by weight to 0.08% by weight based upon the total weight of all components in the composition.

5. The method according to claim 1, wherein the composition comprises i) 3- (4-chloro-6-fluoro-2-trifluoromethylbenzimidazol-7-yl)-l-methyl-6-trifluoromethyl- 2,4(lH,3H)pyrimidinedione and ii) a second herbicide.

6. The method according to claim 5, wherein the second herbicide is selected from the group consisting of N-(phosphonomethyl)glycines, aryloxyalkanoic acids, ureas, imidazolinones, hydroxybenzonitriles, sulfonylureas, 2-(4-aryloxy- phenoxy)alkanoic acids, benzothiadiazinones, 2-chloroacetanilides, arenecarboxylic acids, pyridyloxyacetic acids, aryl triazolinones, isoxazolidinones, sulfonanilides, anilides, dinitroanilines, benzoylcyclohexanediones, picolinic acids, cyclohexene oximes and triazolones.

7. The method according to claim 6, wherein the second herbicide is selected from the group consisting of glyphosate, 2,4-D, MCPA, MCPP, isoproturon, imazapyr, imazamethabenz, imazethapyr, imazaquin, ioxynil, bromoxynil, chlorimuron, chlorsulfuron, bensulfuron, pyrazosulfuron, thifensulfuron, triasulfuron, fenoxaprop, fluazifop, quizalofop, diclofop, bentazone, butachlor, metolachlor, acetochlor, dimethenamide, dicamba, fluroxypyr, sulfentrazone, carfentrazone-ethyl, clomazone, florasulam, diflufenican, pendimethalin, mesotrione, clopyralid, tralkoxydim and flucarbazone.