WO2024179934A1 - Composition - Google Patents

Composition Download PDF

Info

Publication number
WO2024179934A1
WO2024179934A1 PCT/EP2024/054647 EP2024054647W WO2024179934A1 WO 2024179934 A1 WO2024179934 A1 WO 2024179934A1 EP 2024054647 W EP2024054647 W EP 2024054647W WO 2024179934 A1 WO2024179934 A1 WO 2024179934A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition according
solvent
methyl
composition
agrochemical
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.)
Ceased
Application number
PCT/EP2024/054647
Other languages
English (en)
Inventor
Reinhard Berger
Celine Meunier
Alexander Schaetz
Robin Wesley
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.)
Syngenta Crop Protection AG Switzerland
Original Assignee
Syngenta Crop Protection AG Switzerland
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 Syngenta Crop Protection AG Switzerland filed Critical Syngenta Crop Protection AG Switzerland
Publication of WO2024179934A1 publication Critical patent/WO2024179934A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents

Definitions

  • the present invention relates to compositions comprising an agrochemical and a solvent, together with methods of preparing and using the same.
  • solubility of active ingredients is limited on the basis of intrinsic molecular and crystallographic properties such as the enthalpy of fusion.
  • active ingredients such as agrochemicals
  • the physicochemical interactions between the solute and the solvents must be maximised in order to provide dissolution energy as a driving force to keep the solute in solution. This is typically achieved by the matching of the polarity of the active ingredient to the polarity of a solvent, phenomenologically described as "like dissolves like".
  • NMP /V-methyl-2-pyrrolidone
  • EC Emulsifiable Concentrate
  • HSP Hansen Solubility Parameters
  • compositions according to the invention also permit the preparation of stable emulsions upon dilution in water while avoiding crystallisation of the agrochemical.
  • 'water-immiscible' is defined herein as a component that has a water miscibility of 0.4 wt% or less at 25 °C. Conversely, a component is 'water-miscible' if it has a water miscibility of greater than 0.4 wt% at 25 °C.
  • agrochemical formulations are applied by diluting the concentrated product into water and spraying on to a field or crop.
  • Typical dilution rates are 1 parts concentrate to 99 parts water (i.e., 1% dilution) and for a diluted EC, some or all of the solvent(s) will dissolve into the water during this process depending on the water miscibility of the solvent.
  • a water- immiscible solvent most of the solvent will not dissolve and will leave a sufficient quantity of emulsion droplets to solubilise the active ingredient.
  • a water-miscible solvent most of the solvent will dissolve into the dilution water and remove the ability of the diluted formulation to solubilise the active ingredient.
  • HSP Hansen Solubility Parameters
  • HSP details of agrochemicals have been obtained based on their chemical structures represented by SMILES strings by employing the in-built QSAR model for HSP predictions using BIOVIA COSMOquick 2022, Dassault Systems, 2021, Version 22.0.0. References: Hornig, M. & Kia mt, A. COSMOfrag: A Novel Tool for High-Throughput ADME Property Prediction and Similarity Screening Based on Quantum Chemistry, J Chem Inf Model, 2005, 45, 1169-1177; Loschen, C. & Klamt, A. COSMOquick: A Novel Interface for Fast o-Profile Composition and Its Application to COSMO-RS Solvent Screening Using Multiple Reference Solvents, Ind. & Eng. Chem. Res. 2012, 51, 14303.
  • the solvent may comprise a substituted phenyl, preferably wherein the phenyl ring is substituted at two positions.
  • the solvent comprises a substituted benzaldehyde, such as an alkoxybenzaldehyde.
  • the solvent comprises methoxybenzaldehyde (anisaldehyde), preferably:
  • the solvent comprises 4-methoxybenzaldehyde (4-anisaldehyde, para- anisaldehyde).
  • the solvent may contain a blend of 4-methoxybenzaldehyde and 2-methoxybenzaldehyde, or a blend of 4-methoxybenzaldehyde and 3-methoxybenzaldehyde.
  • the solvent contains no or substantially no /V-methylpyrrolidone (NMP).
  • the agrochemical is selected from one or more of the agrochemicals set out in Table A below.
  • the HSP parameters of 4-methoxybenzaldehyde are provided for reference and, as discussed above, if the RED value is below 1 the agrochemical is within the relevant solubility sphere.
  • the agrochemical is selected from one or more of Metalaxyl, Pirimicarb, Napropamide, Pyroquilon, Cyproconazole, Picoxystrobin, Clodinafop propargyl, Aclonifen, Acetochlor, Pyraclostrobin, Propiconazole, Butafenacil, Fomesafen, Lufenuron, Rynaxypyr, Chlorothalonil, Difenoconazole, Pydiflumetofen (Adepidyn®), azoxystrobin, pinoxaden, Isocyloseram (Plinazolin®), Benzovindiflupyr (Solatenol®), Spiropidion, Phenetylarylamide (Tymirium®), sedaxane, and isopyrazam.
  • the agrochemical is preferably present in a quantity of least 2% by weight, preferably at least 5%, advantageously the agrochemical is present in a quantity of even greater than 10% by weight, such as greater than 20% by weight.
  • composition comprising 4- methoxybenzaldehyde and one or more of:
  • R2 is halogen, Ci-Cehaloalkyl, Ci-C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, Ci- C4haloalkylsulfonyl, Ci-Cehaloalkoxy, Ci-C4haloalkylsulfonyloxy or Cs-Cecycloalkyloxy;
  • Xi is O or NR5
  • Gi is N or CH
  • G2 is C-R2a or N;
  • R2a is hydrogen or R2a forms, together with R2, the group -O-CF2-O-
  • Q is a radical selected from the group consisting of formula Qa, Qb, Qc and Qd
  • X is S, SO, SONH or SO 2 ;
  • Ri is Ci-C4alkyl or C3-C6cycloalkyl-Ci-C4alkyl
  • Qi is hydrogen, halogen, Ci-Cehaloalkyl, Cs-Cecycloalkyl, Cs-Cecycloalkyl monosubstituted by cyano, Ci-Cecyanoalkyl, Ci-Cecya noalkoxy, Ci-Cehaloalkoxy, -N(R4) 2 , -N(R4)COR4, - N(R4)CON(R4) 2 , (oxazolidin-2-one)-3-yl, 2-pyridyloxy, N-linked pyrazolyl which is unsubstituted or is mono-substituted by chloro, cyano or trifluoromethyl, N-linked triazolyl or C-linked pyrimidinyl; wherein each R4 is independently hydrogen, Ci-C4alkyl or Cs-Cecycloalkyl; and
  • R3 is hydrogen, halogen or Ci-C4alkyl
  • the compound of formula I is represented by the compounds of formula la-1 wherein
  • R2 is Ci-C2haloalkyl or Ci-C2haloalkylsulfonyl; preferably R2 is CF3 or CF3SO2;
  • Xi is O or NCH 3 ;
  • Gi is N or CH
  • R2a is hydrogen or R2a forms, together with R2, the group -O-CF2-O-
  • Q is a radical selected from the group consisting of formula Qa, Qb, Qc and Qd
  • A is N;
  • X is S, SONH or SO 2 ;
  • Ri is Ci-C4alkyl; preferably Ri is ethyl;
  • Qi is hydrogen, Cs-Cecycloalkyl, Cs-Cecycloalkyl monosubstituted by cyano, Ci-Cecya noalkyl, Ci-Cecya noalkoxy, N-linked pyrazolyl which is unsubstituted or is mono-substituted by chloro, cyano or trifluoromethyl, N-linked triazolyl or C-linked pyrimidinyl;
  • R3 is hydrogen, halogen or Ci-C4alkyl; preferably R3 is hydrogen; and
  • Rs, R9, Rio and Rn are, independently from each other, hydrogen or Ci-Cehaloalkyl; preferably Rs and Rio are hydrogen and R9 and Rn are CF3; or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula la-1.
  • R2 is Ci-C2haloalkyl or Ci-C2haloalkylsulfonyl; preferably R2 is CF3 or CF3SO2;
  • Q is a radical selected from the group consisting of formula Qc and Qd
  • X is S, SONH or SO 2 ;
  • Ri is Ci-C4alkyl; preferably Ri is ethyl;
  • R9 and R11 are hydrogen or Ci-C4haloalkyl; preferably R9 and Rn are CF3; or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula I.
  • R2 is Ci-C2haloalkyl or Ci-C2haloalkylsulfonyl; preferably R2 is CF3 or CF3SO2;
  • Xi is O or NCH3; preferably Xi is O when Gi is CH and Xi is NCH3 when Gi is N;
  • Gi is N or CH; preferably Gi is N when R2a is hydrogen and Gi is CH when R2a forms, together with R2, the group -O-CF2-O-;
  • R2a is hydrogen or R2a forms, together with R2, the group -O-CF2-O-;
  • Q is a radical selected from the group consisting of formula Qa and Qb wherein the arrow denotes the point of attachment to the carbon atom of the bicyclic ring;
  • A is N;
  • X is S, SONH or SO 2 ;
  • Ri is Ci-C4alkyl; preferably Ri is ethyl;
  • Qi is hydrogen, Cs-Cecycloalkyl, Cs-Cecycloalkyl monosubstituted by cyano, Ci-Cecya noalkyl, Ci-Cecya noalkoxy, N-linked pyrazolyl which is unsubstituted or is mono-substituted by chloro, cyano or trifluoromethyl, N-linked triazolyl or C-linked pyrimidinyl; preferably Qi is hydrogen, cyanoisopropoxy, cyanoisopropyl, cyanocyclopropyl or N-linked pyrazolyl which is unsubstituted or is mono-substituted by chloro, cyano or trifluoromethyl, N-linked triazolyl or C-linked pyrimidinyl; and
  • R3 is hydrogen; or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula I.
  • compounds of formula la-3a which are compounds of formula la-3 wherein Q is Qa, R 2 is CF3, R 2a is hydrogen, Xi is NCH3, Gi is N and Qi is hydrogen, cyanoisopropoxy, cyanoisopropyl, cyanocyclopropyl or, N-linked triazolyl.
  • compounds of formula la-3b which are compounds of formula la-3 wherein Q is Qa, R 2a forms, together with R 2 , the group -O-CF 2 -O-, Xi is O, Gi is CH and Qi is hydrogen, cyanoisopropoxy, cyanoisopropyl, cyanocyclopropyl or, N-linked triazolyl.
  • R2 is halogen, Ci-Cehaloalkyl, Ci-C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, Ci-
  • Q is a radical selected from the group consisting of formula Qa and Qb wherein the arrow denotes the point of attachment to the carbon atom of the bicyclic ring; and wherein A represents CH or N;
  • X is S, SO, SONH or SO 2 ;
  • Ri is Ci-C4alkyl or C3-C6cycloalkyl-Ci-C4alkyl
  • Qi is hydrogen, Cs-Cecycloalkyl, Cs-Cecycloalkyl monosubstituted by cyano, Ci-Cecya noalkyl, Ci-Cecya noalkoxy, N-linked pyrazolyl which is unsubstituted or is mono-substituted by chloro, cyano or trifluoromethyl, N-linked triazolyl or C-linked pyrimidinyl; preferably Qi is hydrogen, cyanoisopropoxy, cyanoisopropyl, cyanocyclopropyl or N-linked pyrazolyl which is unsubstituted or is mono-substituted by chloro, cyano or trifluoromethyl, N-linked triazolyl or C-linked pyrimidinyl; and
  • R3 is hydrogen; or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula I b-1 or I b-2. and compound of formula (II) below wherein
  • R 1 is CN
  • R 2 is H
  • R 3 is Ci-C2-a Ikyl, Cs-Ce-cycloalkyl, Ci-C2-alkoxy-Ci-C2-alkyl, or Ci-C2-haloalkyl;
  • Z is a bond, or oxygen
  • R 4 is phenyl substituted with 1 to 3 independently selected substituents R 5 , or 5 or 6 membered monocyclic heteroaryl substituted with 1 to 3 independently selected substituents
  • Q is a cyclic amine represented by the formula Ila or a cyclic amine represented by the formula
  • X is hydrogen, or halogen
  • Y is R a SO2, R b R c NSO2, R d SO2N(Ci-C4-alkyl), 5 or 6 membered heteroaryl substituted with 1 to 3 independently selected substituents R 7 , or 5 or 6 membered non-aromatic heterocyclic ring system in which one to three carbons are replaced independently by nitrogen, oxygen, sulphur, or sulfonyl and substituted with 1 to 3 independently selected substituents from halogen, cyano, Ci-Ce-alkyl, Ci-Ce-haloalkyl and C3-C6-cycloalkyl; :
  • A is Ci-Ce-a I ky I, Ci-Ce-cyanoalkyl, Cs-Ce-cyanocycloalkyl, R a SC>2, R b R c NSO2, or 5 or 6 membered heteroaryl substituted with 1 to 3 independently selected substituents R 8 ;
  • R a is Ci-Ce-alkyl, Ci-Ce-haloalkyl, C2-Ce-alkenyl, C2-Ce-haloalkenyl, C2-Ce-alkynyl, C2-C6- haloalkynyl, Cs-Ce-cycloalkyl, or Cs-Ce-halocycloalkyl;
  • R b and R c are independently selected from hydrogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, C2-C6- alkenyl, C2-Ce-haloalkenyl, C2-Ce-alkynyl, C2-Ce-haloalkynyl, Cs-Ce-cycloalkyl and C3-C6- halocycloalkyl;
  • R d is Ci-Ce-alkyl, Ci-Ce-haloalkyl, C2-Ce-alkenyl, C2-Ce-haloalkenyl, C2-Ce-alkynyl, C2-C6- haloalkynyl, Cs-Ce-cycloalkyl, or Cs-Ce-halocycloalkyl;
  • R 5 is independently selected from halogen, cyano, Ci-Ce-a Ikyl, Ci-Ce-haloalkylCs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylsulfonyl, Ci-Ce- haloalkylsulfanyl and -O-Ci-2haloalkanediyl-O-; and
  • R 6 , R 7 and R 8 are independently selected from halogen, cyano, Ci-Ce-a Ikyl, Ci-Ce-haloalkyl, C2- Ce-alkenyl, C2-Ce-haloalkenyl, C2-Ce-alkynyl, C2-Ce-haloalkynyl, Cs-Ce-cycloalkyl, Cs-Ce- halocycloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkylsulfonyl and Ci-Ce-haloalkylsulfanyl; or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer and N-oxide of the compound of formula (II).
  • PCT/EP2022/060093 PCT/EP2023/075142, PCT/EP2023/081407, and EP 23216968.0.
  • formula Q is a cyclic amine of formula Ila in a compound of formula I
  • p 1 and p 2 are each 2
  • R 3 is Ci-Cs-a Ikyl, C3-C4-cycloalkyl, Ci-C2-alkoxy-Ci-C2-alkyl, or Ci-C2-haloalkyl
  • Z is a bond or oxygen
  • R 4 is phenyl substituted with 1 to 3 independently selected substituents from fluorine, bromine, chlorine, cyano, trifluoromethyl, methoxy, trifluoromethoxy, methylsulfonyl, trifluoromethylsulfonyl and O-CF2-O-, or 5 or 6 membered monocyclic heteroaryl substituted with 1 to 3 independently selected substituents from fluorine, chlorine, cyano, methyl, trifluoromethyl, trifluoroethyl, cyclopropyl, methoxy, trifluoromethoxy, methylsulfonyl
  • formula Q is a cyclic amine of formula Ila in a compound of formula I
  • p 1 and p 2 are each 2
  • R 3 is methyl, cyclopropyl, methoxymethyl, difluoromethyl, or trifluoromethyl
  • Z is a bond or oxygen
  • R 4 is phenyl substituted with 1 to 3 independently selected substituents from fluorine, bromine, chlorine, cyano, trifluoromethyl, methoxy, trifluoromethoxy, methylsulfonyl, trifluoromethylsulfonyl and O-CF2-O-, or 5 or 6 membered monocyclic heteroaryl substituted with 1 to 3 independently selected substituents from fluorine, chlorine, cyano, methyl, trifluoromethyl, trifluoroethyl, cyclopropyl, methoxy, trifluoromethoxy, methylsulfonyl and trifluoromethylsulfonyl
  • X is hydrogen
  • Y
  • formula Q is a cyclic amine of formula Ila in a compound of formula I
  • p 1 and p 2 are each 2
  • R 3 is methyl, cyclopropyl, methoxymethyl, difluoromethyl, or trifluoromethyl
  • Z is a bond or oxygen
  • R 4 is phenyl substituted with 1 to 3 independently selected substituents from fluorine, bromine, chlorine, trifluoromethyl, and O-CF2-O-, or 5 membered monocyclic heteroaryl substituted with trifluoroethyl
  • X is hydrogen
  • Y is R b R c NSO2, R d SO2N(isopropyl), 5 membered heteroaryl substituted with methyl, or 5 membered non-aromatic heterocyclic ring system in which one to three carbons are replaced independently by nitrogen, and sulfonyl, which ring is substituted with an ethyl
  • R a is methyl
  • R b and R c
  • formula Q is a cyclic amine of formula lib in a compound of formula I
  • q 1 and q 2 are each 2
  • R 3 is Ci-C2-alkyl, C3-C4-cycloalkyl, methoxymethyl, trifluoromethyl or difluoromethyl
  • Z is a bond, or oxygen
  • R 4 is phenyl substituted with 1 to 3 independently selected substituents from fluorine, bromine, chlorine, cyano, trifluoromethyl, methoxy, trifluoromethoxy, methylsulfonyl, trifluoromethylsulfonyl and O-CF2-O-, or 5 or 6 membered heteroaryl substituted with 1 to 3 independently selected substituents from fluorine, chlorine, cyano, methyl, trifluoromethyl, trifluoroethyl, cyclopropyl, methoxy, trifluoromethoxy, methylsulfonyl and trifluoromethylsulfonyl;
  • q 1 and q 2 are each 2; R 3 is trifluoromethyl or difluoromethyl; Z is oxygen; R 4 is phenyl substituted with 1 to 3 independently selected substituents from fluorine, bromine, chlorine, trifluoromethyl, methoxy, trifluoromethoxy, methylsulfonyl, trifluoromethylsulfonyl and O- CF2-O-; A is R b R c NSO2, R d SO2N(isopropyl), or 5 or 6 membered heteroaryl substituted with 1 to 3 independently selected from fluorine, chlorine, methyl and trifluoromethyl; and R b and R c are independently selected from hydrogen, methyl, and ethyl; and R d is methyl.
  • the compound of formula II is selected from 6-cyclopropyl-2-[(2,2-difluoro-l,3- benzodioxol-5-yl)methoxy]-5-[4-(5-methyl-l,l-dioxo-l,2,5-thiadiazolidin-2-yl)piperidine-l- carbonyl]pyridine-3-carbonitrile; 2-[(2,2-difluoro-l,3-benzodioxol-5-yl)methoxy]-6-
  • the one or more agrochemical is present in an amount of at least 2% by weight, such as at least 5% by weight, or even at least 10% by weight (e.g., from 5 to 50% by weight or from 10 to 55% by weight).
  • compositions described herein may comprise a co-solvent.
  • the co-solvent is selected from one or more of the solvents set out in Table B (trade names provided in parentheses).
  • composition may further comprise a co-formulant, such as a surfactant.
  • a co-formulant such as a surfactant.
  • surfactants are included as emulsifiers, dispersants, and wetting agents.
  • the surfactants useful in the new compositions are known in the art and comprise, for example, salts of alkyl sulphates, such as diethanolammonium lauryl sulphate; salts of arylsulphonates, such as calcium dodecyl-benzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol ethoxylate; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as ethoxylated sorbitol
  • compositions may also comprise additional co-formulants known in the art such as crystallisation inhibitors, viscosity-modifying substances, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, anti-foams, complexing agents, neutralising or pH-modifying substances and buffers, corrosion-inhibitors, fragrances, wetting agents, absorption improvers, micronutrients, plasticisers, glidants, lubricants, dispersants, thickeners, anti-freezes, microbiocides, and also liquid and solid fertilisers.
  • additional co-formulants known in the art such as crystallisation inhibitors, viscosity-modifying substances, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, anti-foams, complexing agents, neutralising or pH-modifying substances and buffers, corrosion-inhibitors, fragrances, wetting agents, absorption improvers, micronutrients, plasticisers, glidants, lubricants, dispersants
  • the composition is advantageously an emulsifiable concentrate (EC), a suspoemulsion (SE), emulsion in water (EW), microemulsion (ME), a capsule suspension (CS), or a mixed formulation of CS and a suspension concentrate (ZC), preferably the composition is an emulsifiable concentrate (EC).
  • EC emulsifiable concentrate
  • SE suspoemulsion
  • ME microemulsion
  • CS capsule suspension
  • ZC suspension concentrate
  • EC emulsifiable concentrate
  • Diluted formulations can be prepared, for example, with water, liquid fertilisers, micronutrients, biological organisms, oil, or solvents.
  • an EC is generally favourable and potentially increases biological performance by a factor of two.
  • the present composition permits the preparation of EC for a range of active ingredients.
  • the present composition also allows for the creation of specialized formulations for specific application techniques such as direct tree injection.
  • a method of preparing a composition as defined herein comprising the dissolution of the agrochemical in the solvent.
  • compositions as defined herein as a pesticide may be used in direct tree injection. Unless otherwise stated, percentages are given as percentages by total weight and all embodiments and preferred features may be combined in any combination.
  • the agrochemical (All) was added into the relevant solvent and the maximum concentration that was able to form a solution is shown in Table 2 below.
  • Solvents 1 and 2 exhibit better solubility properties for the agrochemical when compared to Comparative Solvents 3 to 15, while Comparative Solvents 1 (butyrolactone) and 2 (acetophenone) are not water-immiscible and have an undesirable environmental profile.
  • Table 3 These emulsions were formed by diluting the emulsifiable concentrates at 1% by volume in hard water (500 ppm calcium carbonate) and soft water (20 ppm calcium carbonate) at 15 °C and 30 °C.
  • the stability of the emulsion is visually evaluated by assessing the amount of oil, cream, and sediment after standing for 1 hour, 2 hours, and 24 hours at the respective temperatures and water hardness. Crystallization of the active ingredient is also carefully monitored as a crystallization can induce nozzle blockage during spraying.
  • AIS Isocyloseram
  • Emulsion stability of this emulsifiable concentrates is evaluated as per the methodology of Example 2.
  • Formulation 'EC050 - 2' is a composition according to the invention.
  • Table 8 The formulations were applied by using a Track Sprayer with a white nozzle Lechler LU-120- 08 (filter 25/32M (red), medium droplets). The test was carried out on the whole plant as a curative application one day after infestation where the plants were sprayed in the track sprayer at a rate of 500 L/ha. During spraying, the leaves were kept horizontal using a metal grid. Afterthe spray dried, the plants were placed in a greenhouse chamber (at 60% humidity, 14 h light, temperature of 22°C in the day and 20°C in the night) and were evaluated at 4, 7, and 11 days post-treatment.
  • the results show that the ECO5O formulations 1 and 2 of the agrochemical show superior translaminar efficacy against mites compared to the OD050 and SC050 formulations.
  • the EC050 formulation according to the invention further offers better mite control at lower rates without an adjuvant.
  • compositions of the present invention demonstrate effective solubility of otherwise difficult to dissolve active ingredient and accordingly the formation of otherwise difficult to prepare EC formulations with improved efficacy.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Composition comprenant un produit agrochimique et un solvant, le solvant ayant des paramètres de solubilité de Hansen dans la plage de solubilité de dD = 19,1, dP = 10,0, dH = 7,4 et un rayon HSP de 3 ; et une miscibilité à l'eau de 0,4% en poids ou moins à 25° C
PCT/EP2024/054647 2023-03-02 2024-02-23 Composition Ceased WO2024179934A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB2303057.0 2023-03-02
GBGB2303057.0A GB202303057D0 (en) 2023-03-02 2023-03-02 Composition

Publications (1)

Publication Number Publication Date
WO2024179934A1 true WO2024179934A1 (fr) 2024-09-06

Family

ID=85980301

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2024/054647 Ceased WO2024179934A1 (fr) 2023-03-02 2024-02-23 Composition

Country Status (5)

Country Link
AR (1) AR132004A1 (fr)
GB (1) GB202303057D0 (fr)
PY (1) PY2415715A (fr)
UY (1) UY40658A (fr)
WO (1) WO2024179934A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2026080434A1 (fr) * 2024-10-08 2026-04-16 Eastman Chemical Company Systèmes de solvants pour formulations agrochimiques

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2295090A (en) * 1992-02-07 1996-05-22 Kioritz Corp A method of combatting pinewood nematodes involving hydroxystilbenes
EP2572579A1 (fr) * 2011-09-22 2013-03-27 Bioforsk Composition utile dans la lutte antiparasitaire
US20160227776A1 (en) * 2013-10-02 2016-08-11 Kyoyu Agri Co., Ltd. Composition containing attractant of noxious arthropod comprising plant-derived component and analogue of same
WO2020049493A1 (fr) * 2018-09-06 2020-03-12 Pi Industries Ltd. Composition agrochimique stable
WO2023208447A1 (fr) * 2022-04-25 2023-11-02 Basf Se Concentré émulsifiable ayant un système de solvants à base de benzaldéhyde (substitué)

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2295090A (en) * 1992-02-07 1996-05-22 Kioritz Corp A method of combatting pinewood nematodes involving hydroxystilbenes
EP2572579A1 (fr) * 2011-09-22 2013-03-27 Bioforsk Composition utile dans la lutte antiparasitaire
US20160227776A1 (en) * 2013-10-02 2016-08-11 Kyoyu Agri Co., Ltd. Composition containing attractant of noxious arthropod comprising plant-derived component and analogue of same
WO2020049493A1 (fr) * 2018-09-06 2020-03-12 Pi Industries Ltd. Composition agrochimique stable
WO2023208447A1 (fr) * 2022-04-25 2023-11-02 Basf Se Concentré émulsifiable ayant un système de solvants à base de benzaldéhyde (substitué)

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
"An emulsifiable concentrate having a benzaldehyde-based solvent system ED - Darl Kuhn", IP.COM, IP.COM INC., WEST HENRIETTA, NY, US, 1 March 2023 (2023-03-01), XP013195528, ISSN: 1533-0001 *
"McCutcheon's Emulsifiers & Detergents", 2018, MC PUBLISHING CO.
HANSEN, CHARLES M., JOURNAL OF PAINT TECHNOLOGY, vol. 39, 1967
HORNIG, M.KLAMT, A.: "COSMOfrag: A Novel Tool for High-Throughput ADME Property Prediction and Similarity Screening Based on Quantum Chemistry", J CHEM INF MODEL, vol. 45, 2005, pages 1169 - 1177, XP007917669, DOI: 10.1021/ci0501948
LOSCHEN, C.KLAMT, A.: "COSMOquick: A Novel Interface for Fast a-Profile Composition and Its Application to COSMO-RS Solvent Screening Using Multiple Reference Solvents", IND. & ENG. CHEM. RES., vol. 51, 2012, pages 14303, XP055627770, DOI: 10.1021/ie3023675

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2026080434A1 (fr) * 2024-10-08 2026-04-16 Eastman Chemical Company Systèmes de solvants pour formulations agrochimiques

Also Published As

Publication number Publication date
AR132004A1 (es) 2025-05-21
UY40658A (es) 2024-09-13
PY2415715A (es) 2024-11-25
GB202303057D0 (en) 2023-04-19

Similar Documents

Publication Publication Date Title
EP2375901B1 (fr) Nouvelles suspo-émulsions de produit agrochimique
KR101103840B1 (ko) 우라실계 화합물 및 이를 포함하는 제초제
CA3000803C (fr) Compose heterocyclique condense contenant un groupe oxime ou ses sels, et insecticide agricole et horticole contenant ledit compose et son procede d'utilisation
EP0776894A1 (fr) Derive d'oxazole, son procede de production et herbicide
JP2013166724A (ja) フルミオキサジンの結晶形
EP1891856B1 (fr) Composition herbicide
WO2014089219A1 (fr) Compositions de concentré de suspension aqueuse nématicide
CN100494179C (zh) 脱水啶酰菌胺的新晶型
JP4018148B2 (ja) 耐雨性を改良した農薬組成物
JPWO1997046092A1 (ja) 耐雨性を改良した農薬組成物
CN103153047B (zh) 农用化学品制剂组合物
CN110290704B (zh) 灭害的哒嗪吡唑酰胺类的稳定配制剂
KR20180095871A (ko) 덴드리머 및 그의 배합물
AU2011301365A1 (en) Pesticide preparations containing N-substituted 2-pyrrolidone-4-carbonic acid esters
GB2274780A (en) Herbicidal composition with reduced phytotoxicity
FR2984079A1 (fr) Une nouvelle suspo-emulsion aqueuse
US10377754B2 (en) Hydrazonyl group-containing condensed heterocyclic compound or salt thereof, agricultural and horticultural insecticide comprising the compound, and method for using the insecticide
CN106632122B (zh) 苯并噁唑苯氧羧酸酰胺类化合物及其制备方法
EP3593637B1 (fr) Concentré de régulateur de croissance de plantes et son utilisation
PL94779B1 (pl) Srodek chwastobojczy
CN100358422C (zh) 含丙酯草醚或异丙酯草醚和乙酰辅酶a羧化酶抑制剂的油菜田除草剂组合物
DE19909541A1 (de) Herbizide 2-Aryloxy- bzw. 2-Arylthio-6-arylpyrimidine
RU2820975C2 (ru) Концентрат регулятора роста растений и его применение
KR20210066835A (ko) 수성 현탁상 농약 조성물
CN104507307A (zh) 包括醚-酰胺化合物的植物检疫组合物

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: 24707489

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 24707489

Country of ref document: EP

Kind code of ref document: A1