Cyclobutriflurum suspension concentrate composition

Abstract

The present invention relates to an aqueous suspension concentrate composition useful in agriculture for controlling pests harmful to commercial crops comprising: (i) cyclobutrifluram; (ii) 25 to 125 grams / liter of a vegetable oil; and (iii) 25 to 125 grams / liter of an ethoxylated fatty alcohol.

Description

Technical Field

[0001] The present invention relates to a novel aqueous cyclobutrifluram suspension concentrate composition. Such compositions find use in agriculture for controlling pests harmful to commercial crops.

Background Art

[0002] Cyclobutrifluram is a pesticidal active ingredient having activity against a variety of nematodes and fungi. The cyclobutrifluram molecule is disclosed in WO 2013 / 143811 and WO 2015 / 003951 (both to Syngenta). Cyclobutrifluram provides long-term protection against a wide range of nematode pests and diseases in all major crops and regions. Nematodes not only damage crops but also open the pathway to further fungal infections. Cyclobutrifluram provides excellent control of both nematodes and soil-borne diseases, particularly Fusarium species. By protecting the root tubers, cyclobutrifluram plays an important role in enabling no-till and conservation tillage practices.

[0003] Seed treatment is the application of biological, physical and chemical agents and techniques to seeds to protect healthy crops and improve establishment. Applying the product directly to the seeds is substantially more efficient and effective than the method of protecting crops by spraying. By directly applying a very small amount of a plant protection product to the seeds themselves before sowing, seed treatment protects the germinating seeds as well as the growing plants themselves. It is more environmentally friendly than spraying on crops in the field because of the very low chemical intensity per hectare. However, to treat seeds with a crop protection active ingredient, a very high concentration of a concentrate formulation is required. The most environmentally friendly formulations for seed treatment are aqueous formulations such as suspension concentrate formulations. However, such suspension concentrates typically face certain stability problems such as, for example, precipitation of the active ingredient, problems associated with grinding of the active ingredient during manufacture, long-term low and high temperature storage stability, etc. [Overview of the project] [Problems that the invention aims to solve]

[0004] The present invention aims to provide a stable, high-concentration suspension concentrate (hereinafter also referred to as "SC") formulation of cyclobutrifluram, a newly developed pest-killing active ingredient. In particular, the SC formulation of the present invention provides treated seeds of improved quality.

[0005] Cyclobutriflurum has been developed as a nematicide and also exhibits good activity against soil-borne diseases. One of the best and most environmentally friendly methods of applying pesticides is by seed treatment. The present invention aims to provide an aqueous suspension concentrate containing a high concentration of cyclobutriflurum that can be used in seed treatment.

[0006] A “suspension concentrate,” also known as a flowable concentrate, is a stable suspension of an active ingredient containing water as a fluid, intended to be diluted with water before use. A “flowable suspension” (hereinafter also referred to herein as “FS”) is a stable flowable suspension applied to seeds directly or after dilution. To avoid ambiguity, references to “suspension concentrate” in this application include “flowable suspension.” [Means for solving the problem]

[0007] In the first aspect, as Embodiment 1, the present invention is described as follows: (i) Cyclobutriflurum; (ii) 25 to 125 grams / liter of vegetable oil; and (iii) 25-125 grams / liter of ethoxylated aliphatic alcohols The present invention provides an aqueous suspension concentrate composition containing the following:

[0008] Preferably, the present invention is (i) Cyclobutriflurum; (ii) 50-100 grams / liter of vegetable oil; and (iii) 50-100 grams / liter of ethoxylated aliphatic alcohol The present invention provides an aqueous suspension concentrate composition containing the following:

[0009] More preferably, the aqueous suspension concentrate composition contains 75 to 125 grams / liter of vegetable oil. Most preferably, the aqueous suspension concentrate composition contains 85 to 115 grams / liter of vegetable oil. The vegetable oil may be selected from castor oil, coconut oil, corn oil, cottonseed oil, grapeseed oil, hazelnut oil, linseed oil, olive oil, palm nut oil, coconut oil, peanut oil, rapeseed oil, rice bran oil, safflower oil, sesame oil, soybean oil, sunflower seed oil, and walnut oil. Preferably, the vegetable oil may be selected from rapeseed oil, sunflower oil, castor oil, and soybean oil.

[0010] More preferably, the aqueous suspension concentrate contains 60 to 110 grams / liter of ethoxylated aliphatic alcohol. Most preferably, the aqueous suspension concentrate contains 75 to 100 grams / liter of ethoxylated aliphatic alcohol. Suitable ethoxylated aliphatic alcohols used herein are, for example, those known to those skilled in the art under the brand names AGNIQUE®, ALKONAT®, ARLYPON®, BRIJ®, DEHYDOL®, DISPONIL®, ERCANOL®, EUMULGIN®, GENAPOL®, GLUCOPON®, LUTENSOL®, MERPOXEN®, OLEIL®, ROFALAN®, SURFOM®, UKANIL®, ULTROL®, and WALLIMUL®.

[0011] As Embodiment 2, the present invention provides an aqueous suspension concentrate composition according to Embodiment 1, wherein the aqueous suspension concentrate composition contains 100 to 300 grams / liter of cyclobutrifluram. Preferably, the aqueous suspension concentrate composition contains 150 to 250 grams / liter of cyclobutrifluram. More preferably, the aqueous suspension concentrate composition contains 180 to 220 grams / liter of cyclobutrifluram.

[0012] As Embodiment 3, the present invention provides an aqueous suspension concentrate composition according to Embodiment 1 or 2, wherein the aqueous suspension concentrate composition contains more vegetable oil than ethoxylated aliphatic alcohol. More preferably, the aqueous suspension concentrate composition contains at least 10% more vegetable oil than ethoxylated aliphatic alcohol (measured in grams / liter).

[0013] As Embodiment 4, the present invention is (i) Cyclobutriflurum; (ii) 75 to 125 grams / liter of vegetable oil; and (iii) 60-110 grams / liter of ethoxylated aliphatic alcohols The present invention provides an aqueous suspension concentrate composition according to one of Embodiments 1 to 3, which includes [the specified element].

[0014] As Embodiment 5, the present invention provides an aqueous suspension concentrate composition according to one of Embodiments 1 to 4, wherein the vegetable oil is soybean oil.

[0015] Embodiment 6 provides an aqueous suspension concentrate composition according to any one of Embodiments 1 to 5, wherein the ethoxylated aliphatic alcohol is an oleyl alcohol polyglycol ether. Preferably, the ethoxylated aliphatic alcohol is an oleyl alcohol polyglycol ether having 5 to 20 ethylene oxides.

[0016] Embodiment 7 is provided, which is an aqueous suspension concentrate composition according to any one of Embodiments 1 to 4, further comprising (iv) 20 to 120 grams / liter of pigment. Preferably, the aqueous suspension concentrate composition contains 40 to 100 grams / liter of pigment. More preferably, the aqueous suspension concentrate composition contains 40 to 80 grams / liter of pigment.

[0017] As used herein, the term “pigment” refers to a dye suitable for coloring seeds during seed treatment. This can be very important as it indicates to the operator which seeds have already been treated, thus avoiding unnecessary exposure to the active ingredient. Furthermore, pigments also play a role in deterring birds from eating the treated seeds. Typical pigments used in this suspension concentrate composition are salts of monoazo dyes, for example, calcium salts of monoazo dyes. Preferably, the pigment used in the present invention is red. One example is Pigment Red 48 (4-[2-(5-chloro-4-methyl-2-sulfophenyl)diazenyl]-3-hydroxy-2-naphthalenecarboxylic acid). Further examples of suitable pigments and dyes include CIPigment Red 48 (2-naphthalenecarboxylic acid, 4-[(5-chloro-4-methyl-2-sulfophenyl)azo]-3-hydroxy-, calcium salt, disodium salt, magnesium salt, strontium salt), CIPigment Red 53 (benzenesulfonic acid, 5-chloro-2-[2-(2-hydroxy-1-naphthalenyl)diazenyl]-4-methyl-, barium salt), CIPigment Red 57 (calcium; 4-[(4-methyl-2-sulfophenyl)diazenyl]-3-oxidenaphthalene-2-carboxylate), CIPigment Red 112 (3-hydroxy-N-(2-methylphenyl)-4-[(2,4,5-trichlorophenyl)diazenyl]naphthalene-2-carboxamide), CIPigment Red Examples include 254 (1,4-bis(4-chlorophenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione) and / or Acid red 18 / Food red 7 (trisodium; 7-hydroxy-8-[(4-sulfonatonaphthalene-1-yl)diazenyl]naphthalene-1,3-disulfonate).

[0018] As Embodiment 8, the present invention is (i) 150-250 grams / liter of cyclobutriflurum; (ii) 25 to 125 grams / liter of vegetable oil; (iii) 25 to 125 grams per liter of ethoxylated aliphatic alcohol; and (iv) 40 to 100 grams per liter of pigment To provide an aqueous suspension concentrate composition according to any one of Embodiments 1 to 7, containing the above.

[0019] As Embodiment 9, the present invention (i) 150 to 250 grams per liter of cyclobutrifluram; (ii) 75 to 125 grams per liter of soybean oil; (iii) 60 to 110 grams per liter of oleyl alcohol polyglycol ether; and (iv) 40 to 100 grams per liter of pigment To provide an aqueous suspension concentrate composition according to any one of Embodiments 1 to 8, containing the above.

[0020] As Embodiment 10, the present invention (v) 1 to 30 grams per liter of sulfosuccinate wetting agent; (vi) 5 to 50 grams per liter of butyl polyalkylene oxide block copolymer; and (vii) 2.5 to 35 grams per liter of sodium lignosulfonate To further provide an aqueous suspension concentrate composition according to any one of Embodiments 1 to 9, containing the above.

[0021] Those skilled in the art are familiar with the sulfosuccinate wetting agents defined in Embodiment 10. An example of a sulfosuccinate wetting agent is sodium dioctyl sulfosuccinate. Examples of such wetting agents are sold under the trade names AEROSOL®, AGENT®, AGNIQUE®, CELANOL®, CELESTOL®, DISPONIL®, EMULSOGEN®, ENZURPON®, GEROPON®, LANKROPOL®, LIOVAC®, MONAWET®, MULTIWET®, NEKAL®, NEWKALGEN®, OCTOWET®, REWOPOL®, STEPWET®, TRITON®, and UMECTANTE®.

[0022] As used herein, butyl polyalkylene oxide block copolymers are nonionic surfactants known to those skilled in the art. These are marketed under brand names including AGUARD®, AGITAN®, AGNIQUE®, ANTAROX®, ATLAS®, BREOX®, CONTEX®, EMKAROX®, EMULGEN®, EMULSOGEN®, EMULSON®, MACOL®, NEWPOL®, PLURACOL®, POLYGLYKOL®, PPG-BUTETH®, SURFONIC®, SYNALOX®, SYNERGEN®, TERGITOL®, TERMUL®, TOXIMUL®, UCON®, ULTRARIC®, and WITCONOL®.

[0023] Suitable sodium lignosulfonates used herein include, for example, the brand names BANIREX®, BORRESPERSE®, DIWATEX®, GREENSPERSE®, KRAFTSPERSE®, LIGNOSITE®, MARACARB®, MARASPERSE®, NORLIG®, ORZANS®, POLYFON®, REAX®, REVEAL®, SANEKISP®, TENSIOFIX®, ULTRAZINE®, URZANS®, VANIREX®, VANISPERSE®, VIXIL®, and VIXILEX®, which are known to those skilled in the art.

[0024] In a preferred embodiment, an aqueous suspension concentrate composition according to Embodiment 10 is provided, where the butyl polyalkylene oxide block copolymer is a butyl alcohol polyoxyethylene-polyoxypropylene block copolymer, also known as copolymer butanol PO (propylene oxide) / EO (ethylene oxide).

[0025] Embodiment 11 is provided, which further comprises (viii) 1 to 55 grams / liter of acrylic graft copolymer, an aqueous suspension concentrate composition according to any one of Embodiments 1 to 10. As used herein, typical acrylic graft copolymers are nonionic surfactants known to those skilled in the art and sold under commercial brand names such as ATLOX®, EMULSON®, HYPERMER®, STEP-FLOW®, and TERSPERSE®.

[0026] In a preferred embodiment, an aqueous suspension concentrate composition according to Embodiment 11 is provided, wherein the acrylic graft copolymer comprises a methylacrylic acid main chain.

[0027] In a second embodiment, Embodiment 12 provides a method for reducing or preventing damage to plants caused by nematode or fungicides, which includes applying a composition according to any one of Embodiments 1 to 11 to the seeds of a plant.

[0028] Embodiment 13 provides the method according to Embodiment 12, in which the plant is selected from barley, the heads and stems of Brassica vegetables, beans, carrots, chickpeas, corn, cotton, cowpeas, cucurbits, dried beans, snow peas, green beans, garlic, lentils, lettuce, millet, oats, onions, peanuts, peas, potatoes, rice, rye, sorghum, soybeans, sugar beets, sunflowers, rye wheat, canola, rapeseed, sweet corn, and wheat. Preferably, the plant is selected from barley, wheat, peanuts, and rice.

[0029] The method relates to Embodiment 12 or 13, and the composition relating to any one of Embodiments 1 to 11 contains a further pest-killing active ingredient. [Modes for carrying out the invention]

[0030] As used herein, the terms "composition of the present invention," "composition of the current inventions," or "composition according to the present invention" mean a composition relating to any one of Embodiments 1 to 11.

[0031] Surprisingly, the following advantages of the aqueous suspension concentrate composition of the present invention were found: (a) Long-term storage stability, i.e., the composition does not undergo physical changes such as turbidity, precipitation, or flake formation over a long period of time; (b) Complete suspension of the concentrate when diluted with water; (c) Excellent physical stability of the active ingredient cyclobutrifluram; (d) Reduction of dust off seeds, and thus improved safety when handling treated seeds; (e) Improved seed flowability of treated seeds, i.e., improved ease of application.

[0032] In further embodiments, the present invention provides a method for controlling pests, comprising diluting a composition according to any one of embodiments 1 to 11 with water or a suitable liquid carrier, particularly an aqueous liquid carrier such as a liquid fertilizer, and then applying the diluted composition to plant propagation material, plants, or their habitat. In other embodiments, the diluted composition is applied by inter-row or T-band application. The compositions of the present invention can also be combined with water in a continuous flow device in a spray application apparatus so as to eliminate the need for a holding tank for the diluted product.

[0033] Other active ingredients such as herbicides, plant growth regulators, algaecides, fungicides, bactericides, virucidates, insecticides, acaricides, nematicides, or molluscicides may be present in the suspension concentrate composition of the present invention or may be added as tank mixers to the diluted spray composition prepared therefrom.

[0034] In addition, the soluble concentrated composition of the present invention may further contain other additives. Examples of such additives include toxicity mitigators, thickeners, fluidity enhancers, wetting agents, defoamers, biocides, buffers, chelating agents, lubricants, fillers, drift control agents, deposition accelerators, evaporation retarders, frost protectants, insect attractants, UV protectants, and fragrances. These additives are known to those skilled in the art.

[0035] Examples of suitable antifreezes include 1,2-propylene glycol and / or propane-1,2,3-triol. Examples of defoaming agents include polydimethylsiloxane defoaming compounds and / or emulsions. Examples of thickeners include mineral stabilizers such as clay, such as montmorillonite and attapulgite, and natural polymers such as xanthan gum. Examples of suitable preservatives include 1,2-benzisothiazol-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one and / or 2-bromo-2-nitropropane-1,3-diol.

[0036] The following embodiments further illustrate the present invention, but are not intended to limit its scope. [Examples]

[0037] methodology Dust off These tests are conducted using the well-known "HEUBACH dust-off test."

[0038] In this type of test, treated seeds are subjected to mechanical stress in a rotating drum. A vacuum pump creates an airflow through the rotating drum, a connected glass cylinder, and an attached filter unit. This airflow carries abraded dust particles through the glass cylinder and then through the filter unit, removing them from the rotating drum. Coarse, non-suspended particles are separated and collected in the glass cylinder, while suspended dust particles accumulate in the filter. The amount of suspended dust collected by the filter is measured by gravimetric method.

[0039] The European Seed Treatment Assurance Industry Scheme (ESTA) ensures that treated seeds are not sold that exceed or fall below industrial dust limits, or exceed any legal requirements. The dust limit set by Euroseeds is 4g of dust per 100kg of cereal seeds. In practice, a much lower dust-off value is often desirable because a lower dust-off value reduces the tendency for the SC compound to detach from the seeds, thus reducing the loss / waste of the SC compound.

[0040] seed fluidity This method was developed to measure seed flowability. Seed flowability is evaluated using a standardized funnel compared to untreated seeds (=100%). The funnel is equipped with a pneumatically operated sliding gate. Newly treated seeds are dried for 24 hours and then passed through the funnel. The flowability of the dried seeds is then measured. If the seed flowability of the treated seeds is 80%, this means that the speed at which the treated seeds passed through the funnel was 80% of the speed at which the untreated seeds passed. Generally, high seed flowability is desirable because it means that treated seeds are less likely to be sticky and are more likely to pass through different machines faster during manufacturing, packaging, and sowing processes, thus improving efficiency and reducing seed loss.

[0041] storage Samples of different compositions and comparative compositions according to the present invention are stored at different temperatures and for different periods of time. The following tests are performed before and after storage to determine the storage life and stability of the compositions.

[0042] viscosity Viscosity was directly measured in the vial containing the composition using a Brookfield® viscometer. The measurement was performed using a Spindle 63 at 30 rpm, and the value was obtained after 1 minute.

[0043] Viscosity was measured in newly prepared composition samples at room temperature and / or after accelerated aging storage.

[0044] Particle size distribution (PSD) The particle size distribution was measured using a Cilas 1064 Laser Diffraction Particle Size Analyzer. Droplets of the sample composition were dispersed until a blocking rate of approximately 15-20% was achieved. Ultrasound was irradiated before and during the measurement (60 seconds each).

[0045] D v (50) represents the percentile value. This is a statistical parameter that can be read from the cumulative particle size distribution. D v(50) (also known as the median) indicates that 50% of all particles are smaller than this size.

[0046] The suspension concentrates (compositions C, D, and E) and comparative compositions (compositions A and B) according to the present invention were prepared according to Table 1. All components in Table 1 are in grams / liter.

[0047] [Table 1]

[0048] [Table 2]

[0049] Conclusion: The compositions of the present invention (e.g., compositions "C", "D", and "E") comprising (i) cyclobutriflurum; (ii) 50 to 105 grams / liter of vegetable oil; and (iii) 50 to 100 grams / liter of ethoxylated aliphatic alcohol were shown to have a surprisingly large reduction in dust-off properties compared to comparative compositions A and B, particularly in treated wheat seeds.

[0050] Furthermore, composition D exhibits surprisingly and significantly better dust-off properties than compositions C and E. In particular, the dust-off properties of composition D are, surprisingly, about twice as good as those of compositions C and E for wheat seeds. The dust-off properties of composition D are also better than those of compositions C and E for peanut seeds.

[0051] Comparative composition "A" contains neither vegetable oil nor aliphatic alcohol polyglycol ether, significantly increasing the likelihood of dust-off, meaning a substantial amount of SC compounding is lost from the seed surface.

[0052] Comparative composition "B" contains only one type of additive, namely an aliphatic alcohol polyglycol ether, and has a significantly higher potential for dust removal compared to the composition of the present invention.

[0053] [Table 3]

[0054] Conclusion: For example, compositions C, D, and E of the present invention show a surprisingly significant improvement in the seed flowability of treated seeds compared to comparative compositions A and B.

[0055] Furthermore, surprisingly, composition "D" exhibits the best seed flow characteristics for wheat and rice among all the compositions tested.

[0056] [Table 4]

[0057] Conclusion: The viscosity of composition D is surprisingly much more stable than that of compositions C and E after two months, especially under more extreme temperature conditions such as -18°C and 20°C. This means that after two months of storage, D exhibits lower viscosity and therefore improved physical stability.

[0058] [Table 5]

[0059] conclusion The particle size growth of composition D is surprisingly and significantly smaller than that of C and E after storage for 0.5 months, 2 months, and 3 months, respectively. This means that D exhibits less crystal growth and therefore better physical stability over time compared to C and E.

[0060] Notably, unlike compositions C and E, composition D contains more vegetable oil than ethoxylated aliphatic alcohols. This is thought to contribute to composition D's surprisingly good seed treatment and physical stability properties compared to compositions C and E.

Claims

1. (i) Cyclobutriflurum; (ii) 25 to 125 grams / liter of vegetable oil; and (iii) 25-125 grams / liter of ethoxylated aliphatic alcohols A concentrated aqueous suspension composition containing the following:

2. The aqueous suspension concentrate composition according to claim 1, comprising 100 to 300 grams / liter of cyclobutriflurum.

3. The aqueous suspension concentrate composition according to claim 1 or 2, comprising more vegetable oil than ethoxylated aliphatic alcohol.

4. (ii) 75 to 125 grams / liter of vegetable oil; and (iii) 60-110 grams / liter of ethoxylated aliphatic alcohols An aqueous suspension concentrate composition according to any one of claims 1 to 3, comprising:

5. The aqueous suspension concentrate composition according to any one of claims 1 to 4, wherein the vegetable oil is soybean oil.

6. The aqueous suspension concentrate composition according to any one of claims 1 to 5, wherein the ethoxylated aliphatic alcohol is an oleyl alcohol polyglycol ether.

7. (iv) 20-120 grams / liter of pigment The aqueous suspension concentrate composition according to any one of claims 1 to 6, further comprising:

8. (i) 150-250 grams / liter of cyclobutriflurum; (ii) 25 to 125 grams / liter of vegetable oil; (iii) 25 to 125 grams / liter of ethoxylated aliphatic alcohols; and (iv) 40-100 grams / liter of pigment An aqueous suspension concentrate composition according to any one of claims 1 to 7, comprising:

9. (i) 150-250 grams / liter of cyclobutriflurum; (ii) Soybean oil in quantities of 75 to 125 grams / liter; (iii) 60 to 110 grams / liter of oleyl alcohol polyglycol ether; and (iv) 40-100 grams / liter of pigment An aqueous suspension concentrate composition according to any one of claims 1 to 8, comprising:

10. (v) 1 to 30 grams / liter of sulfosuccinate humectant; (vi) 5 to 50 grams / liter of butyl polyalkylene oxide block copolymer; and (vii) 2.5 to 35 grams / liter of sodium lignosulfonate The aqueous suspension concentrate composition according to any one of claims 1 to 9, further comprising:

11. (viiii) Acrylic graft copolymers of 1 to 55 grams / liter The aqueous suspension concentrate composition according to any one of claims 1 to 10, further comprising:

12. A method for reducing or preventing damage to plants caused by nematode or fungicides, comprising applying the composition described in any one of claims 1 to 11 to the seeds of a plant.

13. The method according to claim 12, wherein the plant is selected from barley, the head and stem parts of Brassica vegetables, beans, carrots, chickpeas, corn, cotton, cowpeas, cucurbitaceae plants, dried beans, snow peas, green beans, garlic, lentils, lettuce, millet, wild oats, onions, peanuts, peas, potatoes, rice, rye, sorghum, soybeans, sugar beets, sunflowers, rye wheat, canola, rapeseed, sweet corn, and wheat.

14. The method according to claim 13, wherein the plant is selected from barley, wheat, peanuts, and rice.

15. The method according to any one of claims 12 to 14, wherein the composition according to any one of claims 1 to 11 further comprises a pest-killing active ingredient.

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