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US-12616202-B2 - Agricultural formulations, uses thereof and processes for preparation thereof

US12616202B2US 12616202 B2US12616202 B2US 12616202B2US-12616202-B2

Abstract

The present invention is directed to an agricultural formulation comprising 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydroinden-4-yl]pyrazole-4-carboxamide, sodium salt of naphthalene sulfonate condensate and tristyrylphenol ethoxylated. The present invention is further directed to a process for preparing the agricultural formulations and methods of use thereof.

Inventors

  • Toshiya Ogawa
  • Ke Zhou
  • Jessica Tanuwidjaja
  • Jane Liu
  • Alice Wei

Assignees

  • VALENT U.S.A. LLC

Dates

Publication Date
20260505
Application Date
20220913

Claims (17)

  1. 1 . An agricultural formulation comprising 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydroinden-4-yl]pyrazole-4-carboxamide, sodium salt of naphthalene sulfonate condensate and tristyrylphenol ethoxylated, wherein the concentration ratio of sodium salt of naphthalene sulfonate condensate to tristyrylphenol ethoxylated is from 10:1 to 1:1.5 or from 1:3 to 1:10.
  2. 2 . The formulation of claim 1 , wherein 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydroinden-4-yl]pyrazole-4-carboxamide is at a concentration from about 1% to about 50% w/w, sodium salt of naphthalene sulfonate condensate is at a concentration from about 0.1% to about 10% w/w and tristyrylphenol ethoxylated is at a concentration from about 0.1% to about 10% w/w, wherein w/w denotes weight by total weight of the formulation.
  3. 3 . The formulation of claim 2 , wherein 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydroinden-4-yl]pyrazole-4-carboxamide is at a concentration from about 20% to about 40% w/w, sodium salt of naphthalene sulfonate condensate is at a concentration from about 2% to about 10% w/w and tristyrylphenol ethoxylated is at a concentration from about 2% to about 10% w/w.
  4. 4 . The formulation of claim 3 , wherein 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydroinden-4-yl]pyrazole-4-carboxamide is at a concentration from about 30% to about 35% w/w, sodium salt of naphthalene sulfonate condensate is at a concentration from about 2% to about 5% w/w and tristyrylphenol ethoxylated is at a concentration from about 2% to about 5% w/w, wherein w/w denotes weight by total weight of the formulation.
  5. 5 . The formulation of claim 1 , wherein the concentration ratio of sodium salt of naphthalene sulfonate condensate to tristyrylphenol ethoxylated is from 5:1 to 1:1.5 or from 1:3 to 1:5.
  6. 6 . The formulation of claim 5 , wherein the concentration ratio of sodium salt of naphthalene sulfonate condensate to tristyrylphenol ethoxylated is from 1:1 to 1:1.5.
  7. 7 . The formulation of claim 5 , wherein the concentration ratio of sodium salt of naphthalene sulfonate condensate to tristyrylphenol ethoxylated is from 1:3 to 1:4.
  8. 8 . The formulation of claim 6 , wherein the concentration ratio of sodium salt of naphthalene sulfonate condensate to tristyrylphenol ethoxylated is from 1:1.33 to 1:1.5.
  9. 9 . The formulation of claim 1 , further comprising one or more excipients selected from the group consisting of propylene glycol, a silicone emulsion, magnesium aluminum silicate, xanthan gum, 19.3% 1, 2-benzisothiazolin-3-one and water.
  10. 10 . An agricultural formulation comprising: from about 20% to about 40% w/w 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydroinden-4-yl]pyrazole-4-carboxamide; from about 2% to about 5% w/w tristyrylphenol ethoxylated; from about 2% to about 5% w/w sodium salt of naphthalene sulfonate condensate; from about 2% to about 10% w/w propylene glycol; from about 0.1% to about 0.4% w/w xanthan gum; from about 0.2% to about 0.6% w/w of a magnesium aluminum silicate; from about 0.1% to about 0.4% w/w silicone emulsion; and from about 0.1% to about 0.3% w/w of 19.3% 1, 2-benzisothiazolin-3-one, wherein w/w denotes weight by total weight of the formulation and wherein the concentration ratio of sodium salt of naphthalene sulfonate condensate to tristyrylphenol ethoxylated is from 1:1 to 1:1.5.
  11. 11 . An agricultural formulation comprising: about 31.25% w/w 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydroinden-4-yl]pyrazole-4-carboxamide; from about 3% to about 4% w/w tristyrylphenol ethoxylated; from about 2% to about 3% w/w sodium salt of naphthalene sulfonate condensate; about 7.5% w/w propylene glycol; about 0.2% w/w xanthan gum; about 0.4% w/w of a magnesium aluminum silicate; about 0.2% w/w silicone emulsion; and about 0.1% w/w of 19.3% 1, 2-benzisothiazolin-3-one, wherein w/w denotes weight by total weight of the formulation and wherein the concentration ratio of sodium salt of naphthalene sulfonate condensate to tristyrylphenol ethoxylated is from 1:1 to 1:1.5.
  12. 12 . A method of protecting plants comprising treating plant propagation material with a fungicidally effective amount of the product of claim 1 .
  13. 13 . A method for controlling or preventing pest damage of plants comprising applying an effective amount of the product of claim 1 to plant propagation material of the plants.
  14. 14 . A method of protecting plants comprising treating plant propagation material with a fungicidally effective amount of the product of claim 10 .
  15. 15 . A method for controlling or preventing pest damage of plants comprising applying an effective amount of the product of claim 10 to plant propagation material of the plants.
  16. 16 . A method of protecting plants comprising treating plant propagation material with a fungicidally effective amount of the product of claim 11 .
  17. 17 . A method for controlling or preventing pest damage of plants comprising applying an effective amount of the product of claim 11 to plant propagation material of the plants.

Description

FIELD OF THE INVENTION The present invention is generally related to an agricultural formulation comprising 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydroinden-4-yl]pyrazole-4-carboxamide, sodium salt of naphthalene sulfonate condensate and tristyrylphenol ethoxylated. The present invention is further directed to a process for preparing the agricultural formulations and methods of use thereof. BACKGROUND OF THE INVENTION Fungal infections are a major concern for crop growers. Fungi can be present on the seed surface prior to planting, they can be soil-borne, or they can be introduced into the growing environment by mobile pests or equipment. Fungi infect seeds and seedlings and destroy plant cells and tissues and thereby prevent seed germination or cause poor development or death of seedlings. Aphanomyces, Fusarium, Helminthosporium, Pythium, and Rhizoctonia are all known to cause infection and death of plants. These organisms cause seed rot, damping-off, seed blight, and root rot. Even diseases that affect adult plants can be controlled by pesticidal seed treatments (e.g., smuts caused by Ustilago, Tilletia, and Urocystis). Metalaxyl is a widely used fungicide for controlling diseases among crops. Metalaxyl is the active ingredient in the seed treatment marketed as Sebring® 318 FS (Sebring is a registered trademark of and available from Nufarm Americas Inc) and Allegiance® FL. However, metalaxyl presents many formulations challenges including its low melting point (63-72° C.) and partial water solubility (8,400 parts per million). Liquid formulations of metalaxyl often form large crystals upon storage. Further, due to its low melting point, formulating metalaxyl with other low-melting point pesticides is highly problematic. To date there is no known finely milled aqueous slurry of metalaxyl and another low-melting point pesticide. Inpyrfluxam (i.e. S-2399; 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydroinden-4-yl]pyrazole-4-carboxamide) is a novel succinate dehydrogenase inhibitor fungicide. Inpyrfluxam presents many formulations challenges including its low co-melting point with metalaxyl (less than 50° C.) and crystal formation in liquid formulations upon storage. There remains a need in the art for physically and chemically stable formulations containing inpyrfluxam and other low-melting point pesticides useful for seed treatment that provides improved protection against fungal pests. Further, there is a need in the art for a process to prepare such physically and chemically stable formulations containing inpyrfluxam and other low-melting point pesticides. SUMMARY OF THE INVENTION The present invention is directed to an agricultural formulation comprising 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydroinden-4-yl]pyrazole-4-carboxamide, sodium salt of naphthalene sulfonate condensate and tristyrylphenol ethoxylated. The present invention is further directed to a method of protecting plants comprising treating plant propagation material with a fungicidally effective amount of an agricultural formulation of the present invention. The present invention is further directed to a method for controlling or preventing pest damage of plants comprising applying to the plant propagation material an effective amount of an agricultural formulation of the present invention onto a plant propagation material. DETAILED DESCRIPTION OF THE INVENTION Applicant has unexpectedly found that a particular ratio of sodium salt of naphthalene sulfonate condensate and tristyrylphenol ethoxylated results in overcoming crystal growth in 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydroinden-4-yl]pyrazole-4-carboxamide formulations. 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydroinden-4-yl]pyrazole-4-carboxamide formulations outside this range do not overcome crystal growth. Milling 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydroinden-4-yl]pyrazole-4-carboxamide, ethaboxam, metalaxyl and mandestrobin together causes crystal growth. Applicant unexpectedly found that formulating 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydroinden-4-yl]pyrazole-4-carboxamide separate from a formulation containing ethaboxam, metalaxyl and mandestrobin and the mixing the two formulations provide a physically stable formulation. Specifically, the Applicant has unexpectedly discovered a stable agricultural formulation comprising 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydroinden-4-yl]pyrazole-4-carboxamide and sodium salt of naphthalene sulfonate condensate and polyoxyethylene tristyrylphenol phosphate, potassium salt. The Applicant has further discovered a stable agricultural formulation comprising 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydroinden-4-yl]pyrazole-4-carboxamide, ethaboxam, metalaxyl, mandestrobin, methyloxirane polymer, sodium salt of naphthalene sulfonate condensate, a mixture of sodium salt of a