Agricultural composition for the control of common grass (Echinochloa crus-galli) and yellow nutsedge (Cyperus sculentus), and a method for controlling weeds.

Description

Agricultural composition for the control of common grass (Echinochloa crus-galli) and yellow nutsedge (Cyperus esculentus), and a method for controlling weeds. Cross-reference for related applications.

[001] This application claims priority over the US Provisional Application 61 / 948.163 filed on March 5, 2014, the description of which is incorporated herein by reference. FIELD OF THE INVENTION

[002] The present invention relates to agricultural compositions useful for killing weeds, and methods of using them. FUNDAMENTALS OF THE INVENTION

[003] Undesirable plants, such as weeds, reduce the amount of resources available to crop plants and can have a negative effect on crop yield. Commonly undesirable plants in crop environments include broadleaf plants and grasses.

[004] Herbicides are used to kill unwanted plants, such as weeds, in crop growing environments. Herbicides are expensive, and their use can result in unintended consequences such as groundwater contamination, environmental damage, herbicide-resistant weeds, and health concerns for humans and mammals. For this reason, it is desirable to minimize the amount of herbicides applied in a crop growing environment or any area in need of weed control.

[005] The herbicide saflufenacil, (N'-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydro-1(2H)-pyrimidinyl)benzyl]-N-isopropyl-N-methylsulfamide), is the active ingredient in the commercially available herbicide Sharpen® (available from BASF Chemical Company). Saflufenacil has some activity against horseweed and some activity against grasses at concentrations Petition 870210058158, dated 06 / 28 / 2021, page 10 / 41 / 13 high concentrations, such as concentrations of at least 0.0025 grams per square meter (0.022 lb ai / acre). However, high rates of saflufenacil can damage crop plants. Furthermore, the Sharpen® product label warns that the product should not be applied to soybeans with herbicides such as sulfentrazone or flumioxazin as a tank mix or as a sequential application within 30 days of planting because it may result in crop damage. (1 lb = 0.453 kg)

[006] The herbicide flumioxazin, (2-[7-fluoro-3,4-dihydro-3-oxo-4(2-propynyl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindol-1,3(2H)dione), is the active ingredient in the commercially available herbicide Valor® (available from Valent USA Corporation). Valor® provides excellent residual control of broadleaf weeds such as Palmer amaranth and water hemp. Valor® is also an excellent pre-emergence herbicide. However, flumioxazin has limited control over horseweed (Conyza canadensis) and growing grasses. Flumioxazin is not used as a post-emergence herbicide.

[007] Herbicides such as flumioxazin and saflufenacil are protoporphyrinogen oxidase (PPO) inhibitors and use a membrane-disrupting mechanism to destroy leaf tissue. PPO is a naturally occurring enzyme in plants that is crucial for chlorophyll formation. When PPO inhibitors prevent PPO activity, singlet oxygen accumulates within plant cells and disrupts cell membranes.

[008] The herbicide 2,4-Dichlorophenoxyacetic acid (“2,4-D”) is a synthetic auxin plant hormone. 2,4-D causes stem curling, leaf wilting, and eventual plant death by increasing plant growth to an unsustainable rate. 2,4-D is used for the control of broadleaf weeds; however, 2,4-D has limited activity on small fleabane and no activity on grasses.

[009] Undesirable plants such as weeds can reduce Petition 870210058158, dated 06 / 28 / 2021, page 11 / 41 / 13 considerably reduces crop yields. For example, a horseweed infestation has been reported as responsible for an 80% reduction in soybean yields. Bruce, JA, and JJ Kells, Horseweed (Conyza canadensis) control in no-tillage soybeans (Glycine max) with preplant and emergence herbicides, Weed Technol. 4:642-647 (1990). For this reason, weed control, and especially grasses and horseweed, is a major concern for crop producers.

[0010] Furthermore, glyphosate-resistant horseweed and other grasses are becoming resistant to glyphosate. Since 2000, glyphosate-resistant horseweed has been reported in Delaware. Glyphosate-resistant horseweed has since been reported in several states. Consequently, there is a need for new products that can provide effective mortality rates for glyphosate-resistant horseweed.

[0011] No-till farming has increased in popularity because it has many benefits, including reduced labor time and decreased soil erosion. However, one of the disadvantages of no-till farming is that weeds are more difficult to control in these areas because they are not tilled. Consequently, there is an increased need for alternative means to manage weed infestation.

[0012] In summary, there is a need for a formulation that reduces the amount of herbicides required to achieve sufficient weed control while minimizing damage to crop plants. As more weeds become herbicide-resistant, alternative formulations with high weed control are desired. Furthermore, as no-till farming continues to increase in popularity, there is a greater need for effective herbicides. A formulation with effective weed control and a lower dosage rate will lead to increased crop yields and reduced concerns about the health of the environment, humans, and mammals. SUMMARY OF THE INVENTION Petition 870210058158, dated 06 / 28 / 2021, page 12 / 41 / 13

[0013] In one aspect the invention is directed to agricultural compositions comprising an effective amount of saflufenacil, an effective amount of flumioxazin, and an effective amount of 2,4-D.

[0014] In another aspect, the invention is directed to methods for controlling weeds comprising applying a composition comprising an effective amount of saflufenacil, an effective amount of flumioxazin, and an effective amount of 2,4-D to an area in need of weed control. DETAILED DESCRIPTION OF THE INVENTION

[0015] It was surprisingly discovered that the combination of saflufenacil with flumioxazin and 2,4-D allowed for more effective control of horseweed and grasses when compared to the application of each of the individual components of the composition or any combination of two components. It was unexpected that the combination of saflufenacil with flumioxazin and 2,4-D resulted in mortality rates better than twice the amount of saflufenacil alone. The synergy of the combination of saflufenacil, flumioxazin, and 2,4-D was also unexpected.

[0016] In one embodiment, the invention is directed to agricultural compositions comprising an effective amount of saflufenacil, an effective amount of flumioxazin, and an effective amount of 2,4-D. Preferably, the compositions of the present invention contain a saflufenacil to flumioxazin ratio of about 1:1.5 to about 1:6 and a saflufenacil to 2,4-D ratio of about 1:11 to about 1:50. In a more preferred embodiment, the compositions of the present invention contain a saflufenacil to flumioxazin ratio of about 1:2 to about 1:6 and a saflufenacil to 2,4-D ratio of about 1:15 to about 1:50. In a more preferred embodiment, the compositions of the present invention contain a saflufenacil to flumioxazin ratio of about 1:3 to about 1:6 and a saflufenacil to 2,4-D ratio of about 1:25 to about 1:50. Petition 870210058158, dated 06 / 28 / 2021, p. 13 / 41 / 13

[0017] In another embodiment, the invention is directed to methods for controlling weeds comprising applying a composition comprising an effective amount of saflufenacil, an effective amount of flumioxazin, and an effective amount of 2,4-D to an area in need of weed control.

[0018] In a further embodiment, the compositions of the present invention are applied in an area in need of post-emergence weed control.

[0019] In yet another embodiment, the invention is directed to methods for controlling weeds wherein the weeds are horseweed (Conyza canadensis), large-clawed millet (Digitaria sanguinalis), Palmer amaranth (Amaranthus palmeri), broadleaf signalgrass (Brachiaria platyhylla), common grass (Echinochloa crus-galli), yellow nutsedge (Cyperus esculentus), and eclipta (Eclipta prostrate). In a preferred embodiment, the weed controlled is horseweed.

[0020] In a preferred embodiment, herbicides are applied simultaneously or sequentially to an area in need of weed control.

[0021] In a further embodiment, the invention is directed to agricultural compositions comprising a synergistic amount of saflufenacil, flumioxazin, and 2,4-D.

[0022] In a preferred embodiment, the invention is directed to methods in which the effective amount of saflufenacil is from about 0.0011 to about 0.0050 grams per square meter (g / m2) (from about 0.01 to about 0.045 lb ai / acre). In a preferred embodiment, the amount of saflufenacil is from about 0.0011 to about 0.0034 grams per square meter (g / m2) (from about 0.010 lb ai / acre to about 0.030 lb ai / acre), more preferably from about 0.0012 to about 0.0028 grams per square meter (g / m2) (from about 0.011 lb ai / acre to about 0.025 lb ai / acre), and most preferably from about 0.0019 Petition 870210058158, dated 06 / 28 / 2021, p. 14 / 41 / 13 to approximately 0.0026 grams per square meter (g / m2) (from approximately 0.017 lb ai / acre to approximately 0.023 lb ai / acre). (1 lb = 0.453 kg)

[0023] In a preferred embodiment, the invention is directed to methods in which the effective amount of flumioxazin is from about 0.0011 to about 0.0112 grams per square meter (g / m2) (from about 0.01 lb ai / acre to about 0.10 lb ai / acre). In a more preferred embodiment, the amount of flumioxazin is from about 0.0045 to about 0.0078 grams per square meter (g / m2) (from about 0.04 lb ai / acre to about 0.07 lb ai / acre), more preferably from about 0.0056 to about 0.0078 grams per square meter (g / m2) (from about 0.05 lb ai / acre to about 0.07 lb ai / acre). In another embodiment, the amount of saflufenacil is approximately 0.0072 grams per square meter (g / m2) (approximately 0.064 lb ai / acre). (1 lb = 0.453 kg)

[0024] In a preferred embodiment, the invention is directed to methods in which the effective amount of 2,4-D is from about 0.0112 to about 0.1121 grams per square meter (g / m2) (from about 0.1 lb ai / acre to about 1.0 lb ai / acre). In a more preferred embodiment, the amount of 2,4-D is from about 0.0224 to about 0.1009 grams per square meter (g / m2) (from about 0.2 lb ai / acre to about 0.9 lb ai / acre), more preferably from about 0.0280 to about 0.0672 grams per square meter (g / m2) (from about 0.25 lb ai / acre to about 0.6 lb ai / acre). In another embodiment, the amount of 2,4-D is preferably from about 0.0504 to about 0.0616 grams per square meter (g / m2) (from about 0.45 lb ai / acre to about 0.55 lb ai / acre), and more preferably from about 0.0560 grams per square meter (g / m2) (0.5 lb ai / acre). (1 lb = 0.453 kg)

[0025] Preferably, the synergistic compositions of the present invention contain a saflufenacil to flumioxazin ratio of about 1:1.5 to about 1:6 and a saflufenacil to 2,4-D ratio of about 1:11 to about 1:50. In a more preferred embodiment, the compositions of the present invention contain a saflufenacil to flumioxazin ratio of about 1:2 Petition 870210058158, dated 06 / 28 / 2021, p. 15 / 41 / 13 at approximately 1:6 and a saflufenacil to 2,4-D ratio of approximately 1:15 to approximately 1:50. In a more preferred embodiment, the compositions of the present invention contain a saflufenacil to paraflumioxazin ratio of approximately 1:3 to approximately 1:6 and a saflufenacil to 2,4-D ratio of approximately 1:25 to approximately 1:50.

[0026] The applicants' mixtures can be applied by any convenient means. Those skilled in the art are familiar with application methods that include foliar applications such as spraying, chemigation (a process of applying the mixture through the irrigation system), granule application, or impregnation of the mixture with fertilizer.

[0027] The applicants' mixtures can be applied as concentrated formulations or as ready-to-use formulations.

[0028] The term “effective amount” means the amount of the formulation that will kill a weed. The “effective amount” will vary depending on the concentration of the formulation, the type(s) of plant(s) being treated, the severity of the weed infestation, the desired result, and the life stage of the weeds during treatment, among other factors. Thus, it is not always possible to specify an exact “effective amount.” However, an appropriate “effective amount” in any individual case can be determined by those skilled in the art.

[0029] The herbicide mixtures of the present invention can be formulated to contain adjuvants, such as solvents, cake-preventive agents, stabilizers, defoamers, slip agents, humectants, dispersants, wetting agents, thickening agents, emulsifiers, and preservatives that increase the long-lasting activity of the active ingredients. Other components that enhance the biological activity of these ingredients may optionally be included.

[0030] Methylated seed oil (“MSO”) is an adjuvant that Petition 870210058158, dated 06 / 28 / 2021, p. 16 / 41 / 13 improves the penetration of an agricultural active ingredient into the leaf cuticle, such as a plant growth regulator, fungicide, or herbicide. MSO can be used in the mixtures of the present invention, but it is not required or responsible for the synergy of the combination of saflufenacil, flumioxazin, and 2,4-D. Other oil-based adjuvants with similar qualities can also be used, such as crop oil concentrates.

[0031] The mixtures of the present invention can be formulated to contain a liquid solvent. Examples of solvents include water or oil concentrates.

[0032] The applicant's mixtures may also include one or more additional herbicides.

[0033] The mixtures of the present invention can be applied in any environment requiring weed control. The environment requiring weed control may include any area where it is desired to have a reduced number of weeds or to be weed-free. For example, the herbicide combination can be applied to an area used for growing crops such as a field, orchard, or vineyard. For example, the applicants' methods and compositions can be applied to areas where soybeans, corn, peanuts, and cotton are growing. In a preferred embodiment, the mixture is applied to an area where a broadleaf crop (soybean, cotton, peanut, orchard, vineyard, forage) is growing. The mixtures of the present invention can also be applied to non-agricultural areas requiring weed control such as lawns, golf courses, or parks.

[0034] The applicants’ compositions and methods can be successfully applied to glyphosate-resistant crops and weeds. The composition and methods can also be applied in areas where genetically modified crops (“GMOs”) or non-GMO crops are being grown. The term “GMO crops” as used herein refers to crops Petition 870210058158, dated 06 / 28 / 2021, page 17 / 41 / 13 that are genetically modified.

[0035] When used in this application, horseweed refers to Conyza canadensis, large digitate millet refers to Digitaria sanguinalis, Palmer amaranth refers to Amaranthus palmeri, broadleaf brachiaria refers to Brachiaria platyhylla, common grass refers to Echinochloa crus-galli, yellow nutsedge refers to Cyperus esculentus, and eclipta refers to Eclipta prostrata. Although the composition of the present invention has proven synergistic when applied to horseweed and grasses, the synergistic composition can be applied to several other weeds or undesirable plants for effective control and is not limited to the examples. These may include giant ragweed (Ambrosia trifida), common ragweed (Ambrosia artemisiifolia), and Chinese jute (Abutilon theophrasti).

[0036] From beginning to end of this request, the singular forms “um”, “uma”, and “o, a” include plural references unless the context clearly dictates otherwise.

[0037] As used herein, “lb ai / acre” is an abbreviation for pounds of active ingredient per acre. (1 lb = 0.453 kg)

[0038] As used herein, all numerical values ​​relating to quantities, percentages by weight and the like are defined as “about” or “approximately” each particular value, plus or minus 10%. For example, the phrase “at least 5.0% by weight” should be understood as “at least 4.5% to 5.5% by weight”. For this reason, quantities within 10% of the claimed values ​​are enclosed within the scope of the claims.

[0039] As used herein, “post-emergence” refers to a herbicide treatment that is applied to an area after weeds have germinated and emerged from the soil or growing medium.

[0040] As used herein, synergy means that when combined, the claimed composition achieves a result that is greater than the expected result. Petition 870210058158, dated 06 / 28 / 2021, page 18 / 41 / 13

[0041] These representative embodiments are by no means limiting and are described only to illustrate some aspects of the invention.

[0042] Furthermore, the following example is offered for illustrative purposes only and not as a limitation. example Example 1.

[0043] The following field trial was conducted during the spring in Mississippi. Sharpen® was used in the trial as the saflufenacil source. Valor® was used in the trial as the flumioxazin source. Roundup Ready soybeans (Glycine max) were used in the trial as the crop plant. All treatments contained 1% w / w MSO concentrated oil.

[0044] When the test began, the test plot had horseweed 6 to 20 inches tall. Applications were administered at the following concentrations. Saflufenacil was administered at 0.0012, 0.0019, or 0.0025 grams per square meter (0.011, 0.017, or 0.022 lb ai / acre) (indicated in the table as “S” followed by the quantity). Flumioxazin was administered at 0.0072 grams per square meter (g / m2) (0.064 lb ai / acre), and 2,4-D was administered at 0.0560 grams per square meter (g / m2) (0.5 lb ai / acre) from the beginning to the end of the experiment. Three days after treatment (3 DAT), soybeans were planted in front of the plot. On day 7 (DAT), another pass of soybeans was planted in front of the plot with a 30-inch planter. Each test was (1 lb = 0.453 kg)

[0045] On day 11 (DAT), readings were taken to determine the survival of horseweed and typed millet. On day 12 (DAT), readings were taken to determine the survival of Palmer amaranth, broadleaf signalgrass, common grass, yellow nutsedge, and eclipta. Survival rates were determined by counting the number of live and dead plants at the time of reading. The phytotoxicity of each treatment was also evaluated by examining the soybeans on days 11 and 12 (DAT). All data were analyzed using the test of Petition 870210058158, dated 06 / 28 / 2021, page 19 / 41 / 13 Bartlett and with a p-value of 0.5 to determine the significance of the results. The results of this study can be seen below in Table 1. The effect of Saflufenacil, flumioxazin, and 2,4-D in weeds. TABLE 1. The effect of SAflufenAcil, Flumioxazina and 2,4-D on weeds Treatments of the following plants: Fleabane, Large-leaved millet, Palmer amaranth, Broadleaf brachiaria, Common grass, Yellow nutsedge, Eclipta. Control (untreated): 0 0 0 0 0 0 0 S 0.011 66.7 43.3 91.0 31.7 31.7 23.3 83.0 S 0.017 78.3 60.0 91.3 45.0 41.7 35.0 91.3 S 0.022 86.7 56.7 96.0 31.7 25.0 30.0 93.0 Flumioxazin 15.0 70.0 96.0 45.0 45.0 42.5 86.3 Flumioxazin S 0.011 61.7 73.3 99.0 54.3 46.0 51.7 92.0 Flumioxazine S 0.017 85.0 81.7 97.7 58.3 54.3 25.0 96.3 Flumioxazine S 0.022 87.7 84.0 99.0 62.7 62.7 36.7 94.7 2.4-D 11.7 50.0 91.0 21.7 15.0 8.3 91.0 Flumioxazine 2.4-D 35.0 70.0 99.0 66.2 63.3 35.0 93.0 2.4-DS 0.011 73.3 78.3 99.0 51.0 46.0 45.0 91.7 2.4-DS 0.017 75.0 79.3 99.0 66.0 63.3 58.3 97.7 2.4-DS 0.022 95.3 90.0 97.0 75.0 68.3 51.0 96.3 2.4-D Flumioxazine S 0.011 95.3 96.3 99.0 97.0 96.3 97.0 99.0 2.4-D Flumioxazine S 0.017 94.7 94.7 99.0 98.3 96.3 94.3 99.0 2.4-D Flumioxazine S 0.022 95.7 96.3 99.0 94.7 95.7 95.0 99.0

[0046] The results illustrate that the combination of saflufenacil, flumioxazin, and 2,4-D is synergistic as it allows for a lower application of saflufenacil while achieving effective mortality rates. The combination of 0.0012 grams per square meter (g / m2) (0.011 lb ai / acre) of saflufenacil, 0.0072 grams per square meter (g / m2) (0.064 lb ai / acre) of flumioxazin, and 0.0560 grams per square meter (g / m2) (0.5 lb ai / acre) of 2,4-D had a higher mortality rate than saflufenacil alone, or saflufenacil with flumioxazin, saflufenacil with 2,4-D, or flumioxazin with 2,4-D. (1 lb = 0.453 kg)

[0047] In addition, treatments with the mixture of the three components allowed a smaller total amount of herbicide to be applied to an area in need of weed control, by reducing the total rate required of any one- or two-way mixture to obtain a quantity Petition 870210058158, dated 06 / 28 / 2021, page 20 / 41 / 13 equivalent of weed control.

[0048] The applicants used the widely accepted fraction method to determine synergy. The fraction method does not simply involve adding together the individual control percentages, as these will often be greater than 100%. The fraction method involves taking the control as a decimal value (X), multiplying the values ​​1 minus X together, then taking the value “minus 1” to have the control calculated as a decimal value. For example, if two products give 60% control, the additive or assumed value will be 84% and not 120%. See Rao, VS, Principles of Weed Science, second edition, (2000) 351-352, and the illustrative example below. Example Calculation Component % Control Response as decimal (1-response) A 60.00 0.6000 0.4000 B 60.00 0.6000 0.4000 0.1600 0.8400 is the multiplication of (1-Response). is calculated additive control. A+B Additive Calc = 84.00 % Control A+B Real = 95.30 % Control

[0049] When the fraction method is applied to the applicant’s data, it reveals evidence of synergy. The graph below shows the calculations of the theoretical additive control and compares it with the actual control of the combination. As seen below, the predicted additive control was approximately 75%. In contrast, the applicants surprisingly found that the 3-way combination provided 95% control. Synergy Calculation % Alone X = decimal Y = (1-X) A Saflufenacil 67.00 0.6700 0.3300 B 2,4-D 12.00 0.1200 0.8800 C Flumioxazin 15.00 0.1500 0.8500 0.2468 0.7532 is (YA*YB*YC) is 1-(YA*YB*YC) Additive Calc = 75.32% of Control Real = 95.00% of Control

[0050] The applicants found that each component of the 3-way combination contributed to the synergy. For example, when saflufenacil was applied to horseweed alone, it provided 67% control. Petition 870210058158, dated 06 / 28 / 2021, page 21 / 41 / 13 Flumioxazin with 2,4-D provided 35% control. Saflufenacil should have increased control from 35% to 78% if the combination was simply additive. The actual increase was to 95%, significantly higher, which is evidence of synergy.

[0051] Similarly, 2,4-D alone provided 12% control and saflufenacil with flumioxazin provided 62% control. 2,4-D should have only increased control from 62% to 66% if the combination was simply additive. The actual increase was to 95%, significantly higher, which is evidence of synergy.

[0052] Finally, flumioxazin alone provided a control of 15%, and 2,4-D with saflufenacil provided a control of 73%. Flumioxazin should have only increased the control from 73% to 77% if the combination was simply additive. The actual increase was to 95%, significantly higher, which is evidence of synergy. The evidence of synergy was also consistent across all three replicates.

[0053] The applicants also verified that their 3-way combination resulted in a statistically significant difference as determined by Bartlett's test and with a p-value of 0.5 to determine the significance of the results.

[0054] Additionally, applicants found that the treatment was non-phytotoxic to soybean crops. This finding allows the treatments to be applied in areas where growing crops are in need of weed control.

Claims

1. Agricultural composition for the control of common grass (Echinochloa crus-galli) and yellow nutsedge (Cyperus esculentus), characterized in that it comprises an effective amount of saflufenacil, an effective amount of flumioxazin and an effective amount of 2,4-dichlorophenoxyacetic acid (2,4-D), wherein the ratio of saflufenacil to flumioxazin is 1:2 to 1:6, and the ratio of saflufenacil to 2,4-D is 1:15 to 1:

50.

2. Agricultural composition according to claim 1, characterized in that the ratio of saflufenacil to flumioxazin is 1:3 to 1:6 and the ratio of saflufenacil to 2,4-D is 1:25 to 1:

50.

3. A method for controlling weeds, characterized in that it comprises applying an effective amount of saflufenacil, an effective amount of flumioxazin, and an effective amount of 2,4-dichlorophenoxyacetic acid (2,4-D) to an area in need of weed control, wherein the ratio of saflufenacil to flumioxazin is 1:2 to 1:6, and the ratio of saflufenacil to 2,4-D is 1:15 to 1:50, and wherein the weeds are common grass (Echinochloa crus-galli) and yellow nutsedge (Cyperus esculentus).

4. Method according to claim 3, characterized in that the effective amount of saflufenacil is from 0.0011 to 0.0034 grams per square meter (g / m2), the effective amount of flumioxazin is from 0.0045 to 0.0078 grams per square meter (g / m2) and the effective amount of 2,4-D is from 0.0224 to 0.0672 grams per square meter (g / m2).

5. Method according to claim 4, characterized in that the effective amount of saflufenacil is from 0.0012 to 0.0026 grams per square meter (g / m2), the effective amount of flumioxazin is from 0.0056 to 0.0078 grams per square meter (g / m2) and the effective amount of 2,4-D is from 0.0448 to 0.0672 grams per square meter (g / m2).

6. Method according to claim 3, characterized in that the ratio of saflufenacil to flumioxazin is 1:3 to 1:6 and the ratio of saflufenacil to 2,4-D is 1:25 to 1:

50.

7. Method according to claim 3, characterized in that saflufenacil, flumioxazin and 2,4-D are applied simultaneously or sequentially to the area in need of weed control.