WO2025155603A1 - Mélanges inhibiteurs de nitrification - Google Patents

Mélanges inhibiteurs de nitrification

Info

Publication number
WO2025155603A1
WO2025155603A1 PCT/US2025/011681 US2025011681W WO2025155603A1 WO 2025155603 A1 WO2025155603 A1 WO 2025155603A1 US 2025011681 W US2025011681 W US 2025011681W WO 2025155603 A1 WO2025155603 A1 WO 2025155603A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
aig
combined
compound selected
mixture partner
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/US2025/011681
Other languages
English (en)
Inventor
Peter BAAS
Steven Brown
Adel Hamza
David M. Jones
David Mann
Jeffrey Petkus
John C. ROHANNA
Greg SCHULENBERG
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Corteva Agriscience LLC
Original Assignee
Corteva Agriscience LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Corteva Agriscience LLC filed Critical Corteva Agriscience LLC
Publication of WO2025155603A1 publication Critical patent/WO2025155603A1/fr
Anticipated expiration legal-status Critical
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C05—FERTILISERS; MANUFACTURE THEREOF
    • C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
    • C05G3/00—Mixtures of one or more fertilisers with additives not having a specially fertilising activity
    • C05G3/90—Mixtures of one or more fertilisers with additives not having a specially fertilising activity for affecting the nitrification of ammonium compounds or urea in the soil
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P21/00—Plant growth regulators
    • C—CHEMISTRY; METALLURGY
    • C05—FERTILISERS; MANUFACTURE THEREOF
    • C05C—NITROGENOUS FERTILISERS
    • C05C1/00—Ammonium nitrate fertilisers
    • C—CHEMISTRY; METALLURGY
    • C05—FERTILISERS; MANUFACTURE THEREOF
    • C05C—NITROGENOUS FERTILISERS
    • C05C3/00—Fertilisers containing other salts of ammonia or ammonia itself, e.g. gas liquor
    • C—CHEMISTRY; METALLURGY
    • C05—FERTILISERS; MANUFACTURE THEREOF
    • C05C—NITROGENOUS FERTILISERS
    • C05C5/00—Fertilisers containing other nitrates
    • C05C5/02—Fertilisers containing other nitrates containing sodium or potassium nitrate
    • C—CHEMISTRY; METALLURGY
    • C05—FERTILISERS; MANUFACTURE THEREOF
    • C05C—NITROGENOUS FERTILISERS
    • C05C9/00—Fertilisers containing urea or urea compounds
    • C05C9/005—Post-treatment
    • C—CHEMISTRY; METALLURGY
    • C05—FERTILISERS; MANUFACTURE THEREOF
    • C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
    • C05G3/00—Mixtures of one or more fertilisers with additives not having a specially fertilising activity
    • C05G3/60—Biocides or preservatives, e.g. disinfectants, pesticides or herbicides; Pest repellants or attractants

Definitions

  • Nitrogen is an essential element for plant health.
  • bound nitrogen for plant nutrition can be present in the form of ammonium compounds or nitrates.
  • the ammonium form of nitrogen is preferred because it is readily incorporated into plants.
  • nitrate nitrogen must be reduced to ammonium by the plant before it can be used – an energetically costly process.
  • Ammonium nitrogen, having a positive charge, is tightly bound to growing media.
  • Nitrogen in the form of nitrate is negatively charged, water soluble, not tightly bound to growing media and is readily washed out.
  • Ammonia-oxidizing bacteria of the genera Nitrosomonas and Nitrobacter oxidize ammonium nitrogen to nitrate nitrogen via nitrite nitrogen. This process is known as nitrification. The extent of nitrification is dependent on the temperature, type of growing medium, pH, moisture content and biological activity. The nitrification process leads to ammonium nitrogen loss and nitrate nitrogen creation. As much as half of applied nitrogen fertilizer is lost within a year, and an undesirable concentration of nitrate in the groundwater is promoted by this process.
  • nitrification inhibitors including linoleic acid, a-linoleic acid, methyl-p- coumarate, methyl ferulate, MHPP, Karanjin, brachialacton, 2-chloro-6-trichloromethylpyridine (nitrapyrin), dicyandiamide, 3,4-dimethylpyrazole phosphate, 4-amino-1,2,4-triazole hydrochloride, 1-amido-2-thiourea, 2-amino-4-chloro-6-methylpyrimidine, 5-ethoxy-3- trichloromethyl-1,2,4-thiodiazole, 2-sulfanilamidethiazole, 3,5-dimethyltetrahydro-1,3,5- thiadiazine-2-thione (dazomet).
  • Nitrification inhibition has been disclosed in the following publications: US 3,494,757 and US 3,635,690, German Laid Open Application DOS 2,745,833 and GB 1,592,516. See also U.S. 3,050,380 Goring; GB 970,663 Watkins; US 3,533,774 Nault; US 4,673,429 Rieber, et al; US 4,925,476 Wagner et al; US 2015/0052960 Makin et al; US 2017/0036969 Nave et al; US 2020/0352162 Cunningham et al; WO 2015/158853 Nave et al; WO 2020/002472 Cunningham et al; WO 2020/020765 Nesvadba et al; WO 2020/020777 Nesvadba et al.
  • nitrification inhibitors lack traits that are beneficial to their users.
  • dazomet is known to have a very non-specific action and attack non-target bacteria in growing media, especially in soil.
  • Nitrification inhibition is also useful for lowering the production of nitrate in growing media – particularly in soil – thereby reducing the amount unwanted nitrate in groundwater.
  • Methods of employing the compounds include applying to and/or incorporating into growing media (e.g., soil) an effective amount of nitrification-inhibiting alkynyl heterocycle.
  • growing media e.g., soil
  • Preferred compounds include an ethynyl-thiazole, an ethynyl-oxazole, an ethynyl-isoxazole, or mixtures thereof.
  • growing medium and growing media are defined as materials in which plants grow.
  • Exemplary growing media include, but are not limited to, soil, perlite, pumice, vermiculite, zeolite, compost, peat moss, coconut coir, sand, silt, clay, water, bark, sawdust, water, and limestone.
  • Exemplary growing media may be outdoor-soil-based or hydroponic.
  • alkyl refers to a C 1 – C 6 branched or unbranched group consisting of carbon and hydrogen atoms.
  • Alkyl groups include for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, i- butyl, s-butyl, t-butyl and the like.
  • alkoxy refers to a O-C 1 – C 6 group where the oxygen atom is connected to a C 1 – C 6 branched or unbranched alkyl group.
  • Alkoxy groups include for example methoxy, ethoxy, propoxy, iso-propoxy, butoxy, iso-butoxy, sec-butoxy, tert-butoxy and the like.
  • thioalkyl refers to a S-C 1 – C 6 group, branched or unbranched, where the sulfur atom is connected to a C 1 – C 6 alkyl group.
  • Thioalkyl groups include for example thiomethyl, thioethyl, thiopropyl, thioisopropyl, thiobutyl, thioisobutyl, thiosecbutyl, thiotertbutyl, and the like.
  • cycloalkyl refers to a C 3 – C 6 group where the carbon atoms form a carbocyclic ring.
  • Cycloalkyl groups include for example cyclopropane, cyclobutane, cyclopentane, cyclohexane and the like.
  • alkenyl refers to a C 2 – C 6 to a branched or unbranched group consisting of carbon and hydrogen atoms and having one or more double bonds between carbon atoms.
  • Alkenyl groups include for example ethylene, propene, 1-butene, 2-butene, isobutene and the like.
  • cycloalkenyl refers to a C 3 – C 6 where the carbon atoms form a carbocyclic ring and contain one or two double bonds.
  • Cycloalkenyl groups include for example cyclopropene, cyclobutene, cyclopentene, cyclohexene, cyclopentadiene, 1,4-cyclohexadiene and the like.
  • halo refers to halogen atoms such as F, Cl, Br, and I.
  • haloalkyl refers to a C 1 – C 6 branched or unbranched alkyl group where one or more hydrogen atoms has been replaced with a halogen atom.
  • Haloalkyl groups include for example fluoromethyl, difluoromethyl, trifluoromethyl, chloroethyl, bromoethyl, iodobutyl, dichloroethyl, and the like.
  • haloalkoxy refers to a C 1 – C 6 group where the oxygen atom is connected to a C 1 – C 6 branched or unbranched alkyl group where one or more hydrogen atoms has been replaced with a halogen atom.
  • Halolkoxy groups include for example trifluoromethoxy, difluoroethoxy, chloropropoxy, bromo-iso-propoxy, dibromobutoxy, and the like.
  • haloalkenyl refers to a C 2 – C 6 to a branched or unbranched group consisting of carbon and hydrogen atoms where one or more hydrogen atoms has been replaced with a halogen atom and having one or more double bonds between carbon atoms.
  • Haloalkenyl groups include for example 1-chloroethylene, 3,3-difluoropropene, 4-bromo-1-butene, and the like.
  • N-oxide includes any compound which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety. N-oxides may be formed for example through oxidation of tertiary amines, such as pyridine, by hydrogen peroxide.
  • salts and agriculturally acceptable salts include hydrofluorides, hydrochlorides, hydrobromides, hydroiodides, nitrates, hydrogensulfates, sulfates, dihydrogenphosphates, hydrogenphosphates, phosphates, carbonates, bicarbonates, oxalates, and C 1 – C 6 branched or unbranched alkanoates – such as formates, acetates, n-propionates, i-propionates, and the like.
  • carrier includes a liquid or solid carrier.
  • a carrier may include an organic or inorganic carrier.
  • Exemplary liquid carriers include, but are not limited to: water; petroleum fractions or hydrocarbons, such as mineral oil, aromatic solvents, paraffinic oils, and the like; vegetable oils, such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; esters of the above vegetable oils; esters of monoalcohols or dihydric, trihydric, or other lower polyalcohols (4-6 hydroxy containing), such as 2-ethyl hexyl stearate, n- butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, di-butyl adipate, di-octyl phthalate and the like; esters of mono, di and polycarboxylic acids and the like; toluene;
  • Exemplary solid carriers include, but are not limited to: silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, pyrophyllite clay, attapulgus clay, kieselguhr, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, cereal meal, tree bark meal, wood meal, nutshell meal, cellulose powders, and mixtures thereof.
  • Fertilizers including but limited to, fertilizers comprising ammonia may be used as carriers.
  • exemplary fertilizers comprise, but are not limited to, anhydrous ammonium, ammonium salts such as ammonium nitrate, calcium ammonium nitrate, ammonium sulfate nitrate, ammonium sulfate or ammonium phosphate; organic ammonia sources, such as manure, biogas, worm castings, compost, seaweed or guano; urea-containing fertilizers such as, urea, formaldehyde urea, urea ammonium nitrate solution, urea sulfur, urea ammonium sulfate, or other urea-based fertilizers.
  • surfactant or surfactants include, but are not limited to: the alkali metal salts, alkaline earth metal salts and ammonium salts of fatty acids or of aromatic sulfonic acids (e.g., lignosulfonic acids, phenolsulfonic acids, naphthalenesulfonic acids, and dibutylnaphthalenesulfonic acid); alkyl- and alkylarylsulfonates; alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates; salts of sulfated hexa-, hepta- and octadecanols; salts of fatty alcohol glycol ethers; condensates of sulfonated naphthalene and its derivatives with formaldehyde; condensates of naphthalen
  • stabilizer includes compounds or ingredients that enhance the stability of active ingredients by decreasing undesirable reactions of active ingredients.
  • Stabilizers may be employed to enhance storage stability of formulated or unformulated active ingredients.
  • stabilizers may decrease undesirable oxidation, reduction, condensation, hydrolysis, addition, elimination, ionic, or free radical reactions.
  • Exemplary stabilizers include, but are not limited to, oxygen scavengers, free radical scavengers, free radical inhibitors, ion scavengers, polymerization inhibitors, and the like.
  • adjuvant includes agriculturally acceptable adjuvants.
  • Exemplary agriculturally acceptable adjuvants include, but are not limited to, crop oil concentrates (e.g., 85% mineral oil + 15% emulsifiers); nonylphenol ethoxylates; benzylcocoalkyldimethyl quaternary ammonium salts; blends of petroleum hydrocarbon, alkyl esters, organic acids, and anionic surfactants; C 9 -C 11 alkylpolyglycoside; phosphate alcohol ethoxylates; natural primary alcohol (C 12 -C 16 ) ethoxylate; di-sec-butylphenol EO-PO block copolymers; polysiloxane-methyl cap; nonylphenol ethoxylate+urea ammonium nitrates; emulsified methylated seed oils; tridecyl alcohol (synthetic) ethoxylates (e.g., 8 EO); tallow amine ethoxylates (e.g., 15 EO); and PEG(
  • Exemplary agriculturally acceptable adjuvants include, but are not limited to, thickening agents (i.e., thickeners).
  • Exemplary thickeners include, but are not limited to, polysaccharides (e.g., xanthan gum), organic and inorganic sheet minerals, and mixtures thereof.
  • Exemplary agriculturally acceptable adjuvants include, but are not limited to, antifoam agents.
  • Exemplary antifoam agents include, but are not limited to, silicone emulsions, long-chain alcohols, fatty acids, fatty acid salts, organofluorine compounds, and mixtures thereof.
  • Exemplary agriculturally acceptable adjuvants include, but are not limited to, antifreeze agents.
  • Exemplary agriculturally acceptable adjuvants include, but are not limited to, adhesives.
  • Exemplary adhesives include, but are not limited to, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, tylose, and mixtures thereof.
  • Compounds and compositions described herein may be formulated for use.
  • Exemplary formulations include, but are not limited to, emulsifiable concentrates, oil dispersions, solution concentrates, suspension emulsions, micro-emulsions, granules, wettable powders, seed treatments, oil-in-water emulsions, water-dispersible granules. Such formulations are described in Chemistry and Technology of Agrochemical Formulations, D.A.
  • an agriculturally effective amount of nitrification inhibiting compound is an amount of compound that produces a measurable effect on one or more of: ammonium nitrogen, nitrification inhibition, nitrate formation, increased plant health, increased plant growth, increased plant or crop yield, bacteria of the genera Nitrosomonas and Nitrobacter.
  • an agriculturally effective amount of an active ingredient is from about 0.0001 grams per hectare to about 5000 grams per hectare, preferably from about 0.0001 grams per hectare to about 500 grams per hectare, and it is even more preferably from about 0.0001 grams per hectare to about 50 grams per hectare.
  • a locus may be: where crops, trees, fruits, cereals, fodder species, vines, turf, and/or ornamental plants, are growing; where domesticated animals are residing; the interior or exterior surfaces of buildings (such as places where grains are stored); the materials of construction used in buildings (such as impregnated wood); and the soil around buildings. Examples provided herein are not exhaustive and should not be construed as limiting. It is understood that a substituent should comply with chemical bonding rules and steric compatibility constraints in relation to the particular molecule to which it is attached. These definitions are only to be used for the purposes of this disclosure.
  • Active Ingredient Group One means the following preferred group of mixture partners that perform multiple agricultural functions selected from the group consisting of 2,4-D, abamectin, acephate, acequinocyl, acetamiprid, acetoprole, acibenzolar, acrinathrin, acynonapyr, afidopyropen, alanycarb, aldicarb, aldimorph, allethrin, alpha-bromadiolone, alpha- cypermethrin, alpha-endosulfan, ametoctradin, amicarbazone, amidoflumet, amidosulfuron, aminocyclopyrachlor, aminopyralid, aminopyrifen, amisulbrom, amitraz, anisiflupurin, aviglycine, azadirachtin, azafenidin, azamethiphos, azimsulfuron, azinphos-ethyl, a
  • Active Ingredient Group Two or “AIG-2” and the term “Active ingredient Group Three” or “AIG-3” refer to groups of nitrification inhibiting compounds which are described in more detail below.
  • Compounds described herein are nitrification inhibitors.
  • One or more compounds described herein may be incorporated into a composition comprising other ingredients such as one or more compounds of AIG-1, carriers, surfactants, and adjuvants.
  • a composition optionally may include a source of ammonia.
  • Sources of ammonia include anhydrous ammonia, urea, urea-ammonium nitrate, and manure.
  • a compound or composition may be mixed directly with the ammonia source.
  • a mixture of compound or composition and ammonia source may be applied directly to a growing medium, such as soil.
  • a compound or composition and the ammonia source may be applied separately to the growing medium, such as soil.
  • a compound or composition and the ammonia source may be applied separately and simultaneously.
  • R 1 R 1 R 1 R N 4 where R 1 – R 4 are independently H, C ⁇ C, C ⁇ C-TMS, C ⁇ CMe, OEt, OMe, OCF 3 , OH, I, Cl, F, methyl, ethyl, cyclopropyl, propyl, SMe, CN, benzyl, acetyl, vinyl, wherein at least one of R 1 – R 4 is C ⁇ C or C ⁇ C-TMS.
  • R 11 and R 14 are independently C ⁇ C, C ⁇ C-TMS, C ⁇ CMe, OEt, OMe, OCF 3 , OH, I, Cl, F, methyl, ethyl, cyclopropyl, propyl, SMe, CN, benzyl, acetyl, vinyl, wherein at least one of R 11 and R 14 is C ⁇ C or C ⁇ C-TMS.
  • R 12 – R 13 are H.
  • R 23 Formula Va, where are independently C ⁇ C, C ⁇ C-TMS, C ⁇ CMe, OEt, OMe, OCF 3 , OH, I, Cl, F, methyl, ethyl, cyclopropyl, propyl, SMe, CN, benzyl, acetyl, vinyl, wherein at least one of R 21 and R 24 is C ⁇ C or C ⁇ C-TMS.
  • R 22 , R 23 , and R 25 are H.
  • a nitrification inhibiting compound, composition, or method provided herein comprises a compound selected from the group (AIG-3) consisting of S N O N O , and agriculturally acceptable salts, N-oxides, stereoisomers, and tautomers thereof.
  • a nitrification inhibiting compound is selected from the group consisting of compounds in Table 1, and agriculturally acceptable salts, N-oxides, stereoisomers, and tautomers thereof.
  • a nitrification composition may be mixed with active ingredients and other mixture partners to enhance the usefulness of the composition.
  • Such active ingredients may have, for example, acaricidal, insecticidal, fungicidal, herbicidal, nematicidal activity, as well as other materials, compounds, and compositions.
  • a composition comprising a compound of Formula I combined with a mixture partner selected from AIG-1.
  • a composition comprising a compound of Formula Ia combined with a mixture partner selected from AIG-1.
  • a composition comprising a compound of Formula II combined with a mixture partner selected from AIG-1.
  • a composition having a compound selected from AIG-3 combined with mixture partner metcamifen. 402. A composition having a compound selected from AIG-3 combined with mixture partner metconazole. 403.
  • a composition according to any of the previous details from 1 through 644 wherein the weight ratio of said compound to said mixture partner is about 50000:1 to about 1:50000. 646.
  • a composition according to any of the previous details from 1 through 644 wherein the weight ratio of said compound to said mixture partner is about 40000:1 to about 1:40000. 647.
  • a composition according to any of the previous details from 1 through 644 wherein the weight ratio of said compound to said mixture partner is about 10256:1 to about 1:10256. 648.
  • a composition according to any of the previous details from 1 through 644 wherein the weight ratio of said compound to said mixture partner is about 10000:1 to about 1:10000. 649. A composition according to any of the previous details from 1 through 644 wherein the weight ratio of said compound to said mixture partner is about 2564:1 to about 1:2564. 650. A composition according to any of the previous details from 1 through 644 wherein the weight ratio of said compound to said mixture partner is 1000:1 to about 1:1000. 651. A composition according to any of the previous details from 1 through 644 wherein the weight ratio of said compound to said mixture partner is about 640:1 to about 1:640. 652. A composition according to any of the previous details from 1 through 644 wherein the weight ratio of said compound to said mixture partner is 500:1 to about 1:500.
  • a composition according to any of the previous details from 1 through 644 wherein the weight ratio of said compound to said mixture partner is 100:1 to about 1:100. 654. A composition according to any of the previous details from 1 through 644 wherein the weight ratio of said compound to said mixture partner is 50:1 to about 1:50. 655. A composition according to any of the previous details from 1 through 644 wherein the weight ratio of said compound to said mixture partner is 20:1 to about 1:20. 656. A composition according to any of the previous details from 1 through 644 wherein the weight ratio of said compound to said mixture partner is about 16:1 to about 1:16. 657. A composition according to any of the previous details from 1 through 644 wherein the weight ratio of said compound to said mixture partner is 10:1 to about 1:10.
  • a composition according to any of the previous details from 1 through 644 wherein the weight ratio of said compound to said mixture partner is 5:1 to about 1:5. 659. A composition according to any of the previous details from 1 through 644 wherein the weight ratio of said compound to said mixture partner is 3:1 to about 1:3. 660. A composition according to any of the previous details from 1 through 644 wherein the weight ratio of said compound to said mixture partner is 2:1 to about 1:2. 661. A composition according to any of the previous details from 1 through 644 wherein the weight ratio of said compound to said mixture partner is 1:1. 662.
  • compositions disclosed herein may exhibit enhanced efficacy may be expected when a compound is combined with a mixture partner at particular weight ratios within the ranges defined above.
  • Enhanced efficacy in this context means an efficacy greater than the expected efficacy as calculated by the Colby equation.
  • Application of Nitrification Inhibitor Compounds to Soil in certain aspects provided herein one or more nitrification inhibitor compounds or compositions are mixed with a source of ammonia.
  • Sources of ammonia include, but are not limited to, anhydrous ammonium, ammonium salts, such as ammonium nitrate, calcium ammonium nitrate, ammonium sulfate nitrate, ammonium sulfate or ammonium phosphate; organic ammonia sources, such as manure, biogas, worm castings, compost, seaweed or guano; urea-containing fertilizers such as, urea, formaldehyde urea, urea ammonium nitrate solution, urea sulfur, urea ammonium sulfate, or other urea-based fertilizers.
  • anhydrous ammonium such as ammonium nitrate, calcium ammonium nitrate, ammonium sulfate nitrate, ammonium sulfate or ammonium phosphate
  • organic ammonia sources such as manure, biogas, worm castings, compost, seaweed or guano
  • one or more of the nitrification inhibitor compounds or compositions are mixed with anhydrous ammonia, which is then injected into the soil.
  • the compound or composition is injected separately into the growing medium at the time of anhydrous ammonia application.
  • the amount of compound or composition present in the anhydrous ammonia mixture, or directly injected, may be adjusted so that an agriculturally effective amount of the nitrification-inhibiting compound or composition is spread.
  • the nitrification inhibitor compound or composition is mixed with fertilizers such as urea-ammonium nitrate solution to form a urea-ammonium nitrate nitrification-inhibitor mixture.
  • mixtures may also include other ingredients such as herbicides, insecticides, fungicides, and safeners.
  • Such mixtures may be applied at rates of from about 10 to about 70 gallons per acre depending on the fertilizer strength and concentration as well as the target amount of nitrogen per acre.
  • the amount of compound or composition present in the treated mixture may be adjusted so that an agriculturally effective amount of the compound or composition is spread.
  • the nitrification compound or composition is impregnated on dry urea. The amount of compound or composition impregnated will depend upon the application rate of the urea. For example, urea may be spread at a rate of from about 200 to about 700 pounds per acre.
  • An amount of compound or composition may be impregnated on dry urea so that the compound or composition is spread at an agriculturally effective amount.
  • the compound or composition is spread as part of a manure slurry mixture.
  • the compound or composition may be mixed with manure prior to application or may be separately applied.
  • the amount of compound or composition present in a manure slurry may be adjusted so that an agriculturally effective amount of compound or composition is spread.
  • a compound or composition may be applied to a growing medium at a rate of from about 50 grams per acre to about 4 kilograms per acre.
  • a compound may be applied to a growing medium at the following rates: 50-60 grams/acre; 60-70 grams/acre; 70-80 grams/acre; 80-90 grams/acre; 90-100 grams/acre; 100-120 grams/acre; 120-140 grams/acre; 140-160 grams/acre; 160-180 grams/acre; 180-200 grams/acre; 200-225 grams/acre; 225-250 grams/acre; 250-275 grams/acre; 275-300 grams/acre; 300-350 grams/acre; 350-400 grams/acre; 400-450 grams/acre; 450-500 grams/acre; 500-550 grams/acre; 550-600 grams/acre; 600-650 grams/acre; 650-700 grams/acre; 700-750 grams/acre; 750-800 grams/acre; 800-850 grams/acre; 850-900 grams/acre; 900-950 grams/acre; 950-1000 grams/acre; 1.0-1.1 kilograms/acre; 1.1-1.2 kilograms/acre; 1.2-1.3 kilograms/acre; 1.3-1.4 kilograms/acre;
  • the vial was placed in a heating block that was warmed to 80 oC and the solution was stirred for 20 h. After the reaction time, the vial was opened to air and aqueous Na 2 CO 3 was added (4 mL). The crude product was extracted with CH 2 Cl 2 and purified by flash chromatography on silica gel.
  • General Procedure F To a 20 mL vial, sodium alkoxide (1.0 equiv.) was charged. Then a solution of aryl halide (1.0 equiv.) in THF (0.2 M concentration of substrate) was added. The vial was placed in a heating block that was warmed to 50 oC and the solution was stirred for 20 h.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Botany (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Soil Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des alcynes hétérocycliques utiles pour l'inhibition de nitrification, des mélanges d'alcynes hétérocycliques et d'autres principes actifs, ainsi que des procédés d'utilisation des alcynes hétérocycliques et des mélanges d'alcynes hétérocycliques et d'autres principes pour l'inhibition de nitrification et l'amélioration du rendement agricole.
PCT/US2025/011681 2024-01-19 2025-01-15 Mélanges inhibiteurs de nitrification Pending WO2025155603A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202463622600P 2024-01-19 2024-01-19
US63/622,600 2024-01-19

Publications (1)

Publication Number Publication Date
WO2025155603A1 true WO2025155603A1 (fr) 2025-07-24

Family

ID=94605761

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2025/011681 Pending WO2025155603A1 (fr) 2024-01-19 2025-01-15 Mélanges inhibiteurs de nitrification

Country Status (1)

Country Link
WO (1) WO2025155603A1 (fr)

Citations (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3050380A (en) 1957-04-16 1962-08-21 Dow Chemical Co Method and product for suppressing the nitrification of ammonium nitrogen in soil
GB970663A (en) 1962-02-07 1964-09-23 Dow Chemical Co Soil treating composition
US3494757A (en) 1968-06-20 1970-02-10 Dow Chemical Co Nitrification inhibitor comprising substituted pyrazoles
US3533774A (en) 1967-03-22 1970-10-13 Dow Chemical Co Composition and method for suppressing the nitrification of ammonium nitrogen in soil
US3635690A (en) 1968-05-16 1972-01-18 Dow Chemical Co Soil treating method and composition for conserving nitrogen in soil by addition of a pyrazole thereto
DE2745833A1 (de) 1977-10-12 1979-04-19 Fahlberg List Veb Mittel zur hemmung bzw. regelung der nitrifikation von ammoniumstickstoff in kulturboeden
GB1592516A (en) 1977-11-02 1981-07-08 Fahlberg List Magdeberg Chemis Method for inhibiting or regulating the nitrification of ammonium nitrogen in cultivated soils
US4673429A (en) 1984-03-14 1987-06-16 Basf Aktiengesellschaft Nitrification-inhibiting 1-hydroxypyrazole derivatives
US4925476A (en) 1987-02-12 1990-05-15 Basf Aktiengesellschaft Azole hemiaminal derivatives and their use as nitrification inhibitors
WO2010012793A1 (fr) * 2008-08-01 2010-02-04 Bayer Cropscience Sa Dérivés d'aminothiazole fongicides
WO2013156433A1 (fr) * 2012-04-17 2013-10-24 Syngenta Participations Ag Dérivés de thiazole actifs en tant que pesticide
US20150052960A1 (en) 2013-08-23 2015-02-26 Koch Agronomic Services, Llc Urease inhibitor and non-ufp solid carrier composition
WO2015158853A1 (fr) 2014-04-17 2015-10-22 Basf Se Inhibiteurs de nitrification d'un nouveau type
WO2018170165A1 (fr) * 2017-03-15 2018-09-20 Metacrine, Inc. Agonistes du récepteur farnésoïde x et leurs utilisations
WO2020002472A1 (fr) 2018-06-28 2020-01-02 Basf Se Utilisation d'alkynylthiophènes en tant qu'inhibiteurs de nitrification
WO2020020765A1 (fr) 2018-07-23 2020-01-30 Basf Se Utilisation d'un composé de thiazolidine substitué en tant qu'inhibiteur de nitrification
WO2020020777A1 (fr) 2018-07-23 2020-01-30 Basf Se Utilisation de 2-thiazolines substituées en tant qu'inhibiteurs de nitrification
US20200352162A1 (en) 2019-05-10 2020-11-12 Silver Defender, Corp. Antimicrobial Adhesives
WO2024020529A2 (fr) * 2022-07-21 2024-01-25 Corteva Agriscience Llc Hétérocycles inhibiteurs de nitrification

Patent Citations (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3050380A (en) 1957-04-16 1962-08-21 Dow Chemical Co Method and product for suppressing the nitrification of ammonium nitrogen in soil
GB970663A (en) 1962-02-07 1964-09-23 Dow Chemical Co Soil treating composition
US3533774A (en) 1967-03-22 1970-10-13 Dow Chemical Co Composition and method for suppressing the nitrification of ammonium nitrogen in soil
US3635690A (en) 1968-05-16 1972-01-18 Dow Chemical Co Soil treating method and composition for conserving nitrogen in soil by addition of a pyrazole thereto
US3494757A (en) 1968-06-20 1970-02-10 Dow Chemical Co Nitrification inhibitor comprising substituted pyrazoles
DE2745833A1 (de) 1977-10-12 1979-04-19 Fahlberg List Veb Mittel zur hemmung bzw. regelung der nitrifikation von ammoniumstickstoff in kulturboeden
GB1592516A (en) 1977-11-02 1981-07-08 Fahlberg List Magdeberg Chemis Method for inhibiting or regulating the nitrification of ammonium nitrogen in cultivated soils
US4673429A (en) 1984-03-14 1987-06-16 Basf Aktiengesellschaft Nitrification-inhibiting 1-hydroxypyrazole derivatives
US4925476A (en) 1987-02-12 1990-05-15 Basf Aktiengesellschaft Azole hemiaminal derivatives and their use as nitrification inhibitors
WO2010012793A1 (fr) * 2008-08-01 2010-02-04 Bayer Cropscience Sa Dérivés d'aminothiazole fongicides
WO2013156433A1 (fr) * 2012-04-17 2013-10-24 Syngenta Participations Ag Dérivés de thiazole actifs en tant que pesticide
US20150052960A1 (en) 2013-08-23 2015-02-26 Koch Agronomic Services, Llc Urease inhibitor and non-ufp solid carrier composition
WO2015158853A1 (fr) 2014-04-17 2015-10-22 Basf Se Inhibiteurs de nitrification d'un nouveau type
US20170036969A1 (en) 2014-04-17 2017-02-09 Basf Se Nitrification inhibitors
WO2018170165A1 (fr) * 2017-03-15 2018-09-20 Metacrine, Inc. Agonistes du récepteur farnésoïde x et leurs utilisations
WO2020002472A1 (fr) 2018-06-28 2020-01-02 Basf Se Utilisation d'alkynylthiophènes en tant qu'inhibiteurs de nitrification
WO2020020765A1 (fr) 2018-07-23 2020-01-30 Basf Se Utilisation d'un composé de thiazolidine substitué en tant qu'inhibiteur de nitrification
WO2020020777A1 (fr) 2018-07-23 2020-01-30 Basf Se Utilisation de 2-thiazolines substituées en tant qu'inhibiteurs de nitrification
US20210340073A1 (en) * 2018-07-23 2021-11-04 Basf Se Use of substituted 2-thiazolines as nitrification inhibitors
US20200352162A1 (en) 2019-05-10 2020-11-12 Silver Defender, Corp. Antimicrobial Adhesives
WO2024020529A2 (fr) * 2022-07-21 2024-01-25 Corteva Agriscience Llc Hétérocycles inhibiteurs de nitrification

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
"Chemistry and Technology of AgrochemicalFormulations", 2012, KLUWER ACADEMIC PUBLISHERS

Similar Documents

Publication Publication Date Title
CN107108386B (zh) 作为硝化抑制剂的炔基吡唑类
JP6743032B2 (ja) 硝化抑制剤としてのピラゾール化合物
CN107580592B (zh) 作为硝化抑制剂的硫醚化合物
RU2731051C2 (ru) Бензилпропаргиловые простые эфиры в качестве ингибиторов нитрификации
CN105051045A (zh) 稠杂环化合物或其盐类和含有该化合物的农业园艺用杀虫剂及其使用方法
JP5112315B2 (ja) ３，４−ジハロゲノイソチアゾール誘導体及び農園芸用植物病害防除剤
CN112424148B (zh) 取代2-噻唑啉作为硝化抑制剂的用途
JPWO2010044215A1 (ja) 光学活性ジフルオロメタンスルホンアニリド誘導体及び除草剤
UA123249C2 (uk) Сполука 4н-піролопіридину або її сіль, сільськогосподарський і садівницький інсектицид, який включає зазначену сполуку або її сіль, і спосіб застосування інсектициду
KR102391897B1 (ko) 논벼 종자 처리제
JP5785934B2 (ja) トリアゾール誘導体及び有害生物防除剤
JP7524067B2 (ja) ムギ類の病害防除方法、ムギ類の種子及びムギ類の倒伏被害抑制方法
JPWO2010070822A1 (ja) 除草剤の薬害軽減剤、薬害が軽減された除草性組成物及びそれを用いる薬害軽減方法
KR102350438B1 (ko) 입상 농약조성물 및 이의 제조방법
JP5039375B2 (ja) イソチアゾール化合物及び農園芸用植物病害防除剤
WO2025155681A1 (fr) Mélanges inhibiteurs de nitrification
CN104529918A (zh) 三氮杂茂化合物、及其运用
JP2010260811A (ja) 含窒素五員ヘテロ環誘導体及び農園芸用植物病害防除剤
JP2016056156A (ja) ピラゾリノン誘導体、その製法及びそれを有効成分として含有する除草剤
JP2016056158A (ja) ピラゾリン−３−オン誘導体、その製法及びそれを有効成分として含有する除草剤

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 25705418

Country of ref document: EP

Kind code of ref document: A1