Improved crop yields

Dithiophosphate seed coatings address the challenge of delivering macronutrients to crops by applying them at low loadings, enhancing growth and yield without inhibiting germination, achieving significant improvements in crop performance.

WO2025207780A1PCT designated stage Publication Date: 2025-10-02HARVEST INCREASE AGRICULTURE LLC +1
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Patent Information

Application Number
PCT/US2025/021566
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Priority Date
2024-03-26
Filing Date
2025-03-26
Publication Date
2025-10-02

AI Technical Summary

Technical Problem

Existing seed coatings for crops like corn and soybeans primarily focus on herbicides, pesticides, and micronutrients, neglecting the application of macronutrients such as NPK and sulfur, which are needed in large quantities and can inhibit germination when applied as thick layers.

Method used

Applying dithiophosphates as seed coatings at low loadings of less than about 2.0 mg/seed, either in solid form or linked through bridging molecules, to provide essential macronutrients like P, K, and S without inhibiting germination.

Benefits of technology

Enhances crop growth and harvest yield by delivering macronutrients effectively, with improvements up to 39% weight gain and 6.4% yield increase, while maintaining seed viability.

✦ Generated by Eureka AI based on patent content.

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Abstract

The present invention includes methods for increasing the yield of plants through the use of seeds, particularly corn and soybean, treated with dithiophosphates prior to planting. Disclosed treatments include applying dry or aqueous solutions of dithiophosphates to seeds that result in loading of the compounds on the seeds at about 2.0 mg / seed or less. The treated seeds are then planted, grown, and harvested.
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Description

IMPROVED CROP YIELDSCLAIM OF PRIORITY

[0001] The present application claims the benefit of US provisional application 63569826, filed on March 26, 2024, which is incorporated by reference.FIELD OF THE INVENTION

[0002] The present invention relates to the treatment of seeds to improve crop yields with dithiophosphates.BACKGROUND OF THE INVENTION

[0003] Dithiophosphates have recently been used to improve the harvest yield of corn and soybeans in the U.S., and they have potential to improve the growth and harvest yields of other crops. An example of a dithiophosphate is dibutyldithiophosphate potassium salt that delivers phosphorus (P), potassium (K), and sulfur (S) to crops. P and K are recognized as macronutrients that are needed at tens of pounds per acre to grow crops such as corn. Sulfur is often called the fourth major nutrient and is often used at loadings of ten pounds per acre to grow corn in the state of Iowa.

[0004] It has been reported that dissolving dibutyldithiophosphate ammonium salt in water and adding this aqueous solution to seeds and the soil around seeds at planting increased the weight of corn plants by up to 39% after four weeks of growth. The effect of dibutyldithiophosphate salt was statistically significant and positive compared to plants grown in its absence when 1, 10, 50, and 75 mg / seed of dibutyldithiophosphate salt were used. In a second study, it was reported that dibutyldithiophosphate potassium salt dissolved in liquid NPK (nitrogen, phosphorus, and potassium) starter fertilizer increased the harvest yield of corn by 6.4% when applied at a loading of 2 kg / acre of dibutyldithiophosphate potassium salt. At an application rate of 0.5 kg / acre of dibutyldithiophosphate, the harvest yield of corn was unaffected. In these studies, dibutyldithiophosphate potassium salt was dissolved in aqueous NPK starter fertilizer and applied as a liquid when the seeds were planted. Based on 35,000 seeds per acre for corn, an application rate of 2 kg / acre yielded 57 mg per seed of the dithiophosphate for a strong, positive effect but at an application rate of 0.5 kg / acre (14 mg / seed) had no observed effect on the harvest yield. Dibutyldithiophosphate has a strong, positive effects at application rates of up to 75 mg / seed, and is effective when added as a liquid to the seed and soil.

[0005] Seed coatings are commonly applied to corn, soybean, wheat, and many other seeds. Only milligram amounts are applied to seeds and typically only herbicides, pesticides, and minute quantities of micronutrients such as zinc are applied. In some instances, microbes are applied as seed coating because these are only needed at sub-milligram or milligram loadings per seed. In contrast, NPK macronutrients and elemental sulfur or sulfate are not applied as seed coatings because they are needed at large quantities that would cover the seeds in a thick layer that would inhibit the germination of seeds.SUMMARY OF THE INVENTION

[0006] The present invention includes applying the detailed dithiophosphates at loadings preferably lower than about 2.0 mg / seed. The present invention also includes these applying dithiophosphates as a solid to the seeds. The present invention also includes the germination, growing, and harvesting of plants from seeds to which these dithiophosphates have been applied, as well as methods for increasing the growth of a plant or the harvest yield of a plant. In one preferred embodiment, these dithiophsphates are applied as a seed coating to seed corn at levels down to about 2.0 mg per seed.DETAILED DESCRIPTION

[0007] The methods of the present invention include utilizing the following dithiphosphates.

[0008] Compound A: The dithiophosphate potassium salt synthesized from propylene glycol with CAS registry number: 929639-19-0 and known as 1,2-Propanediol, cyclic 0,0- phosphorodithioate potassium salt. Compound A has a structure of

[0009] Compound B: The dithiophosphate potassium salt synthesized from phenol with CAS registry number: 3514-82-7 and known as phosphorodithioic acid, O,O-diphenyl ester, potassium salt. Compound B has a structure

[0010] Compound C: The dithiophosphate potassium salt synthesized from ethanol with CAS registry number: 3454-66-8 and known as phosphorodithioic acid, 0,0-diethyl ester, potassium salt. Compound C has a structure of:

[0011] Compound D: The dithiophosphate potassium salt synthesized from 1,3 -propanediol with CAS registry number: 85556-99-6 and known as 1,3 -Propanediol, cyclic 0,0- phosphorodithioate potassium salt. Compound D has a structure of:

[0012] Compound E: The di thiophosphate salt synthesized from N,N-dimethylaminoethanol chloride salt and known as phosphorodithioic acid, O,O-bis[2-(diethylamino)methyl] ester, monohydrochloride. Compound E has a structure of:

[0013] Compound F: The ammonium salt of dibutyldithiophosphate with CAS registry number: 1071-18-7 and known as phosphorodithioic acid, 0,0-dibutyl ester, ammonium salt.Compound F has a structure of:

[0014] Compound G has a structure of:

[0015] Compound H has a structure of:

[0016] Other salts of the illustrated compounds such as sodium, potassium, ammonium, or hydrochloride containing salts are also contemplated.

[0017] The methods of the present invention include applying one or more of these dithiophosphates to a seed wherein the resulting loading of dithiophosphate on the exterior of the seed is less than about 15 mg / seed, less than about 14 mg / seed, less than about 13 mg / seed, less than about 12 mg / seed, less than about 10 mg / seed, 9 mg / seed, less than about 8 mg / seed, less than about 7 mg / seed, less than about 6 mg / seed, 5 mg / seed, less than about 4 mg / seed, less than about 3 mg / seed, less than about 2 mg / seed, less than about 1 mg / seed, less than about 0.9 mg / seed, less than about 0.8 mg / seed, less than about 0.7 mg / seed, less than about 0.6 mg / seed, less than about 0.5 mg / seed, less than about 0.4 mg / seed, less than about 0.3 mg / seed, less than about 0.2 mg / seed, less than about 0.1 mg / seed, 0.05 mg / seed, or 0.01 mg / seed.

[0018] The methods of the present invention include applying one or more of these dithiophosphates to a seed wherein the resulting loading of di thiophosphate on the exterior of the seed is in the range of about 0.01 mg / seed to about 5 mg / seed, in the range of about 0.01 mg / seed to about 4 mg / seed, in the range of about 0.01 mg / seed to about 3 mg / seed, in the range of about 0.01 mg / seed to about 2 mg / seed, or in the range of about 0.01 mg / seed to about 1 mg / seed.

[0019] The methods of the present invention include applying one or more of these dithiophosphates to a seed wherein the resulting average loading of dithiophosphate on the exterior of the seed in the selected sample of coated seed is in the range of about 0.01 mg / seed to about 5 mg / seed, in the range of about 0.01 mg / seed to about 4 mg / seed, in the range of about 0.01 mg / seed to about 3 mg / seed, in the range of about 0.01 mg / seed to about 2 mg / seed, or in the range of about 0.01 mg / seed to about 1 mg / seed.

[0020] The methods of the present invention include applying one or more of these dithiophosphates to a seed in solid form, meaning that no carrier solvent is utilized. For example, dithiophosphates as a powder or particulate can be added to a plurality of seeds under gentleagitation. For instance, the seeds can be a container that is spinning and the solid dithiophosphate is added and the container continues to be spun until the seeds are coated. In another embodiment, the dry material is added prior to the start of agitation of the seeds. Any other method of agitation may also be used when a dry or solid form of the coating material is utilized. In another embodiment, the one or more dithiophosphates are applied to seeds as a liquid or in a liquid solvent, and then dried, so that at the time of transportation or planting, the seed is coated in a dry material. In this embodiment the seeds can be agitated such as in a container that is being spun and the solution of dithiophosphate can be added to the seeds. In another embodiment, the solution is added to the seeds prior to the start of agitation of the seeds. The container is spun until the seeds are judged to be coated. In certain embodiments, the excess liquid is then removed through mechanical means (for example, through filtering), while in other embodiments excess liquid is driven off by increasing the ambient temperature or reducing the ambient pressure to facilitate evaporation of the liquid and leaving the coating material behind as a seed coating. In a preferred embodiment, the costed seeds are air dried.

[0021] In another embodiment, one or more of these dithiophosphates is linked to the seed through a bridging molecule such that the dithiophosphate is covalently bonded, ionically bonded, or physiosorbed to the seed via the bridging molecule. In one embodiment, polymeric dithiophosphate is utilized such that a dithiophosphate monomer acts as the bridging molecule for one or more additional dithiophosphate compounds. In another embodiment, the di thiophosphate is held within or bonded (covalently, ionically, or by physisorption) to a matrix that is applied to the seed.

[0022] In each of these embodiments the dithiophosphate may be applied to the seed with other additives such as herbicides, pesticides, biologies, or micronutrients. Also, a visible or non- visible (e g. ultraviolet fluorescing) dye may be applied as a seed coating to help indicate that the seeds are coated.

[0023] The methods of the present invention may be utilized on any agricultural seed; typically for plants propagated through sexual propagation method, although utilizing these methods with asexual propagation are also contemplated. Preferred agricultural seed included corn, soybeans, wheat, cotton, sorghum, tomatoes, cucumbers, barley, oats, strawberry,blueberry, raspberry, sunflower, canola, flax, sugar cane, sugar beets, and other vegetable, pulses, oil crops, and feed grains crops.

[0024] The methods of the present invention may utilize any of these dithiophosphate:

[0025] Compound A: The dithiophosphate potassium salt synthesized from propylene glycol with CAS registry number: 929639-19-0 and known as 1,2-Propanediol, cyclic 0,0- phosphorodithioate potassium salt. Compound A has a structure of:

[0026] Compound B: The dithiophosphate potassium salt synthesized from phenol with CAS registry number: 3514-82-7 and known as phosphorodithioic acid, O,O-diphenyl ester, potassium salt. Compound B has a structure of:

[0027] Compound C: The dithiophosphate potassium salt synthesized from ethanol withCAS registry number: 3454-66-8 and known as phosphorodithioic acid, 0,0-diethyl ester, potassium salt. Compound C has a structure of:

[0028] Compound D: The dithiophosphate potassium salt synthesized from 1,3 -propanediol with CAS registry number: 85556-99-6 and known as 1,3 -Propanediol, cyclic 0,0- phosphorodithioate potassium salt. Compound D has a structure of:

[0029] Compound E: The di thiophosphate salt synthesized from N,N-dimethylaminoethanol chloride salt and known as phosphorodithioic acid, O,O-bis[2-(diethylamino)methyl] ester, monohydrochloride. Compound E has a structure of:

[0030] Compound F: The ammonium salt of dibutyldithiophosphate with CAS registry number: 1071-18-7 and known as phosphorodithioic acid, 0,0-dibutyl ester, ammonium salt.Compound F has a structure of:

[0031] Compound G has a structure of:

[0032] Compound H has a structure of:

[0033] In one series of trials, com seeds are to be treated with each of Compound A through H in an aqueous solution to achieve 0.2 mg / seed of compound after evaporation of the water and planted. Untreated corns seeds are be planted in adjacent fields to the treated com seeds as a control. The plants will be fertilized according to best practices and grown until harvest. The plants will be harvested and the harvest yields will be measured.

[0034] Field trials were carried out using Compound E, Compound H, Compound D, Compound G, Compound C by applying each compound to corn seeds and soybean seeds according to the following methods and procedures.

[0035] Prior to applying the treatments to com seed, each of the compounds was dissolved in approximately 3x by weight water except for Compound C which was dissolved in 4x by weight water. For instance, 0.73 grams of Compound G was dissolved in 2.2 m of water. Corn seeds were sprayed with this aqueous solution while being spun in a can. The seeds were sprayed so 0.10 milligrams of one of the compound was applied per seed. The can was spun until all water evaporated. Seeds were separately coated with either Compound E, Compound H, Compound D, Compound G, or Compound C.

[0036] Prior to applying the treatments to soybean seeds, each of the compounds was dissolved in approximately 3x by weight water except for Compound C which was dissolved in 4x by weight water. For instance, 4.84 grams of Compound G was dissolved in 15 mL of water. The soybean seeds were sprayed with this aqueous solution while being spun in a can. The seeds were sprayed so 0.125 milligrams of one of the chemicals was applied per seed. The can was spun until all water evaporated. Seeds were separately coated with either Compound E, Compound H, Compound D, Compound G, or Compound C.

[0037] The entire test field had NPK fertilizer uniformly applied prior to planting. Within the test field, small plot trials with appropriate borders were planted in a randomized fashion such that 10 plots for each compound were planted along with 10 control plots of untreated seeds. Thus 60 small plots were planted with com in the corn test field and 60 small plots were planted with soybeans in the soybean test field. Plants were allowed to grow to maturity under the prevailing weather conditions for the growing season, at which time each small plot was harvested and the harvest yield, in bushels per acre, for each small plot was recorded. The yield of each small plot for a given compound or control was averaged across the 10 small plots, as shown in Table 1 for Com and in Table 2 for soybeans.

[0038] Table 1

[0039] Table 2

[0040] In addition to the salts of the identified compounds, other cations are contemplated to form salts of the compounds disclosed herein. Selection of differing cation for the salts may be used to modify the solubility of the compounds in water or other solvent that may be utilized during seed treatment.

[0041] Throughout the application where the term ‘about’ is used, it means a range of plus- or-minus 5% above and below the stated number. It will be further appreciated that functions or structures of a plurality of components or steps may be combined into a single component or step, or the functions or structures of one-step or component may be split among plural steps or components. The present invention contemplates all of these combinations. Unless stated otherwise, dimensions and geometries of the various structures depicted herein are not intended to be restrictive of the invention, and other dimensions or geometries are possible. Plural structural components or steps can be provided by a single integrated structure or step. Alternatively, a single integrated structure or step might be divided into separate plural components or steps. In addition, while a feature of the present invention may have been described in the context of only one of the illustrated embodiments, such feature may be combined with one or more other features of other embodiments, for any given application. It will also be appreciated from the above that the fabrication of the unique structures herein and the operation thereof also constitute methods in accordance with the present invention. The present invention also encompasses intermediate and end products resulting from the practice of the methods herein. The use of “comprising” or “including” also contemplates embodiments that “consist essentially of’ or “consist of’ the recited feature.

[0042] The explanations and illustrations presented herein are intended to acquaint others skilled in the art with the invention, its principles, and its practical application. Those skilled in the art may adapt and apply the invention in its numerous forms, as may be best suited to the requirements of a particular use. Accordingly, the specific embodiments of the present invention as set forth are not intended as being exhaustive or limiting of the invention. The scope of the invention should, therefore, be determined not with reference to the above description, but should instead be determined with reference to the appended claims, along with the full scope of equivalents to which such claims are entitled. The disclosures of all articles and references, including patent applications and publications, are incorporated by reference for all purposes.

Claims

CLAIMSWhat is claimed is:

1. A method comprising treating a plurality of com seed or soybean seed with one or more of the following compounds: Compound A, Compound B, Compound C, Compound D, Compound E, Compound F, Compound G, or Compound H, or other salts thereof.

2. The method of claim 1 further comprising germinating the treated seeds.

3. The method of claim 2 further comprising growing plants from the treated seeds.

4. The method of claim 3 further comprising harvesting the plants grown from the treated seeds.

5. The method of claim 4 wherein the seeds are corn seeds.

6. The method of claim 4 wherein the seeds are soybean seeds.

7. The method of claim 1 wherein the treating step comprises applying a solution comprising one or more of Compound C, Compound D, Compound E, Compound G, or Compound H, or other salts thereof.

8. The method of claim 7 wherein the treatment step comprises applying an aqueous solution comprising at least Compound E or other salts thereof to the exterior of soybean seeds.

9. The method of claim 7 wherein the treatment step comprises applying an aqueous solution comprising at least Compound G or other salts thereof to the exterior of corn seeds.

10. The method of claim 7 wherein the treating step results in a loading of Compound C, Compound D, Compound E, Compound G, or Compound H, or other salts thereof, in the range between about 0.01 mg / seed and about 2.0 mg / seed.

11. The method of claim 7 wherein the treating step results in a loading of Compound E, or other salts thereof, in the range between about 0.01 mg / seed and about 2.0 mg / seed.

12. The method of claim 7 wherein the treating step results in a loading of Compound G, or other salts thereof, in the range between about 0.01 mg / seed and about 2.0 mg / seed.

13. A method comprising increasing a harvest yield of a seed by treating the seed with one or more of the following compounds: Compound A, Compound B, Compound C, Compound D, Compound E, Compound F, Compound G, or Compound H, or other salts thereof, when compared to the harvest yield of an untreated seed.

14. The method of claim 13 wherein the seed to be treated is selected from corn seed and soybean seed.

15. The method of claim 14 wherein the increasing step comprises applying a solution of one or more of Compound C, Compound D, Compound E, Compound G, or Compound H, or other salts thereof, to a seed prior to planting, growing a plant from the treated seed, and harvesting the plant grown from the treated seed.

16. The method of claim 15 wherein the applying step results in a loading of Compound C, Compound D, Compound E, Compound G, or Compound H, or other salts thereof, in the range between about 0.01 mg / seed and about 2.0 mg / seed.

17. The method of claim 16 wherein the applying step results in a loading of Compound E or other salts thereof, in the range between about 0.01 mg / seed and about 2.0 mg / seed and the seed is soybean seeds.

18. The method of claim 16 wherein the applying step results in a loading of Compound G or other salts thereof, in the range between about 0.01 mg / seed and about 2.0 mg / seed and the seed is corn seed.

19. A method comprising: treating the exterior of a plurality of com seeds or soybean seeds with one or more of the following compounds: Compound A, Compound B, Compound C, Compound D, Compound E, Compound F, Compound G, or Compound H, or other salts thereof; germinating the treated seeds; growing plants from the treated seeds; and harvesting the plants grown from the treated seeds.

Citation Information

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