WO2023017167A1 - Compositions fongicides de metconazole - Google Patents
Compositions fongicides de metconazole Download PDFInfo
- Publication number
- WO2023017167A1 WO2023017167A1 PCT/EP2022/072709 EP2022072709W WO2023017167A1 WO 2023017167 A1 WO2023017167 A1 WO 2023017167A1 EP 2022072709 W EP2022072709 W EP 2022072709W WO 2023017167 A1 WO2023017167 A1 WO 2023017167A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- metconazole
- plants
- formulation
- dimethyl
- alkylamide
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 54
- 239000005868 Metconazole Substances 0.000 title claims abstract description 20
- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical group C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 12
- 238000009472 formulation Methods 0.000 claims description 29
- 239000003995 emulsifying agent Substances 0.000 claims description 17
- 241000233866 Fungi Species 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 241000196324 Embryophyta Species 0.000 claims description 7
- 241000209140 Triticum Species 0.000 claims description 5
- 235000021307 Triticum Nutrition 0.000 claims description 5
- 230000003032 phytopathogenic effect Effects 0.000 claims description 5
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims description 4
- 240000004713 Pisum sativum Species 0.000 claims description 4
- 235000010582 Pisum sativum Nutrition 0.000 claims description 4
- 235000021536 Sugar beet Nutrition 0.000 claims description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 4
- HNXNKTMIVROLTK-UHFFFAOYSA-N n,n-dimethyldecanamide Chemical group CCCCCCCCCC(=O)N(C)C HNXNKTMIVROLTK-UHFFFAOYSA-N 0.000 claims description 3
- 230000008635 plant growth Effects 0.000 claims description 3
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims description 2
- 241000223600 Alternaria Species 0.000 claims description 2
- 241001465180 Botrytis Species 0.000 claims description 2
- 240000002791 Brassica napus Species 0.000 claims description 2
- 235000006008 Brassica napus var napus Nutrition 0.000 claims description 2
- 241000220485 Fabaceae Species 0.000 claims description 2
- 206010017533 Fungal infection Diseases 0.000 claims description 2
- 241000223218 Fusarium Species 0.000 claims description 2
- 244000068988 Glycine max Species 0.000 claims description 2
- 235000010469 Glycine max Nutrition 0.000 claims description 2
- 244000020551 Helianthus annuus Species 0.000 claims description 2
- 235000003222 Helianthus annuus Nutrition 0.000 claims description 2
- 240000005979 Hordeum vulgare Species 0.000 claims description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 2
- 241000219745 Lupinus Species 0.000 claims description 2
- 208000031888 Mycoses Diseases 0.000 claims description 2
- 241001503951 Phoma Species 0.000 claims description 2
- 241001291156 Pyrenopeziza Species 0.000 claims description 2
- 241001515786 Rhynchosporium Species 0.000 claims description 2
- 241000221662 Sclerotinia Species 0.000 claims description 2
- 241000209056 Secale Species 0.000 claims description 2
- 235000007238 Secale cereale Nutrition 0.000 claims description 2
- 241001533598 Septoria Species 0.000 claims description 2
- 240000006394 Sorghum bicolor Species 0.000 claims description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 claims description 2
- 235000019714 Triticale Nutrition 0.000 claims description 2
- 235000007264 Triticum durum Nutrition 0.000 claims description 2
- 241000209143 Triticum turgidum subsp. durum Species 0.000 claims description 2
- 235000002096 Vicia faba var. equina Nutrition 0.000 claims description 2
- 240000008042 Zea mays Species 0.000 claims description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 2
- 235000013339 cereals Nutrition 0.000 claims description 2
- 235000005489 dwarf bean Nutrition 0.000 claims description 2
- 244000013123 dwarf bean Species 0.000 claims description 2
- 235000009973 maize Nutrition 0.000 claims description 2
- 241000228158 x Triticosecale Species 0.000 claims description 2
- 230000000694 effects Effects 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 5
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- -1 dusts Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 3
- 239000012752 auxiliary agent Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 229920005682 EO-PO block copolymer Polymers 0.000 description 2
- 239000002202 Polyethylene glycol Chemical class 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 229920001223 polyethylene glycol Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- 240000006063 Averrhoa carambola Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 241000221300 Puccinia Species 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical class [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229940100242 glycol stearate Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
-
- 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
- A01P3/00—Fungicides
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Definitions
- the present invention relates to stable compositions comprising metconazole and use of such compositions in methods of the growth of plants, as well as in methods for controlling, preventing and/or treating of phytopathogenic fungi in crop plants.
- Metconazole is a triazole fungicide, ISO common name for (1 RS,5RS; 1 RS,5SR)-5-(4-chlorobenzyl)-2,2-dimethyl-1-(1 H-1 ,2,4-triazol-1 - ylmethyl)cyclopentanol.
- Metconazole is an effective fungicide and is typically formulated as emulsifiable concentrate at concentrations of 60 g/L and 90 g/L.
- Higher strength (higher load or higher concentration) formulations are desirable for various environmental and economic reasons, such as reduction of packaging and solvents released into environment.
- higher strength formulations are challenging due to chemical and/or physical instability of active ingredient, such as agglomeration, crystallization, phase separation and gelling.
- Desirable requirements for higher strength formulations are storage stability and potency retention, stability at various temperatures and homogeneity and no precipitation at lower temperatures.
- a major limitation of the emulsifiable concentrate of metconazole is its limited stability at low temperature and high concentration.
- the present invention addresses these needs and provides a wide variety of benefits and advantages, such as high strength formulations of metconazole which exhibit chemical and physical stability at broad temperature range.
- fungicidally effective amount means the relative amount that is effective to inhibit or control fungus growth rate, increase mortality, or eradicate the fungus when the fungicidal composition is applied to the target fungus at a given application rate.
- the term “about” when used in connection with numeric values, parameters or numerical ranges such as amounts, volumes, volume ratios, volume percentages, weight ratios, weight percentages, or application rates of ingredients of a composition means an amount, a volume, a volume ratio, a volume percentage, a weight ratio, a weight percentage, or an application rate that is recognized by those of ordinary skill in the art to provide a desired effect equivalent to that obtained from the specified amount, volume, volume ratios, volume percentages, weight ratio, weight percentage, or application rate, is encompassed herein and should be construed in light of the number of reported significant digits and applying ordinary rounding techniques.
- range from 1 to 10 includes all sub-ranges between and including the recited minimal value 1 and the recited maximum value 10 and any value in-between, including any and all decimal values.
- composition comprises at least one active ingredient and at least one auxiliary agent.
- an "active ingredient” is a compound which directly exerts a biologically relevant effect, preferably a pesticidal effect as described herein.
- auxiliary agent refers to a compound or combination of compounds which do not exert a biologically relevant effect of their own but support the effects of the active ingredient(s). When auxiliary agents are used, their choice will depend on the active ingredients and on the procedures selected for the treatment.
- One aspect of the present invention is to provide compositions as described above additionally comprising at least one auxiliary component selected from the group comprising of emulsifiers, solvents, surfactants, carriers, dispersants, thickeners, hydrophobizing agents, moisture-retaining agents, extenders, solid carriers, anti-foaming agents and/or other auxiliaries.
- compositions of the present invention can be formulated into any customary type of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
- Composition types examples are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP), pressings (e.g. BR, TB), granules (e.g. WG, SG, GR), etc.
- suspensions e.g. SC, OD, FS
- emulsifiable concentrates e.g. EC
- emulsions e.g. EW, EO, ES, ME
- capsules e.g. CS, ZC
- pastes e.g. WP, SP, WS, DP
- pressings e.g. BR, TB
- granules e.g. WG,
- composition and “formulation” are used interchangeably throughout the text and are meant as having the same meaning.
- the present invention is directed to high-strength fungicidal formulations containing metconazole.
- the present invention provides a high-strength fungicidal formulation comprising: a) metconazole, wherein the formulation comprises from about 100 g/L to about 450 g/L of metconazole; b) an emulsifier or mixture of emulsifiers from about 50 g/L to about 300 g/L: c) solvent N,N-dimethyl (Ce-Ci2)alkylamide from about 200 g/L to about 700 g/L.
- the emulsifiers according to the present invention can be anionic, cationic or non-ionic in character.
- Emulsifiers conventionally used in the art of formulation and which may also be used in the present formulations are described, for example, in "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, New Jersey, 1998 and in “Encyclopedia of Surfactants", Vol. 1-111 , Chemical publishing Co., New York, 1980- 81.
- Typical emulsifiers include salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkyl and/or arylalkylphenolalkylene oxide addition products, such as nonylphenolCis ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-Cie ethoxylate; soaps, such as sodium stearate; alkylnaphthalenesulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride;
- emulsifier or mixture of emulsifiers is usually present at a concentration of from about 50 g/L to about 300 g/L.
- the solvent which typically makes up the remainder of the high-strength fungicidal formulation, is N,N-dimethyl (C6-Ci2)alkylamide present at concentration from about 200 g/L to about 700 g/l, more preferably from about 400 g/L to about 600 g/L.
- high-strength fungicidal formulation comprises: a) metconazole in concentration from about 200 to about 400 g/L b) an emulsifier or mixture of emulsifiers from about 50 g/L to about 200 g/L; c) solvent N,N-dimethyl (C6-Ci2)alkylamide from about 400 g/L to about 600 g/L.
- the high-strength, fungicidal formulation does not exhibit separation or precipitation (or crystallization) of any of the components at low or high temperatures.
- the high-strength formulation remains a clear solution at temperatures below about 10°C, more preferably at temperatures about 0°C.
- compositions can further comprise one or more agriculturally acceptable adjuvant or auxiliary.
- An adjuvant or an auxiliary in the context of the present invention is a component which enhances the performance effect of the formulation.
- adjuvants and auxiliaries are agents which promote one or more of the following effects: retention, spreading, attachment to the leaf/crop surface, penetration, physical, chemical, technical and/or biological effect, etc.
- One aspect of the present invention is to provide compositions as described above additionally comprising at least one auxiliary component selected from the group comprising of fungicides, emulsifiers, solvents, surfactants, carriers, dispersants, thickeners, anti-foaming agents and/or other auxiliaries.
- compositions of the present invention are diluted with water prior to being applied.
- phytopathogenic fungi are selected from Septoria, Mildew, fungi causing brown rust or yellow rust, Fusarium, Rhynchosporium, Botrytis, Phoma, Alternaria, Sclerotinia and Pyrenopeziza.
- crops or plants are selected from sunflower, maize, sorghum, soybeans, oilseed rape, cereals, sugar beets, peas and other leguminosae, winter and spring wheat, durum wheat, winter and spring barley, triticale, rye, peas, field beans, sugar beet, lupins, grassland, ornamentals, golf courses and lawns.
- a high-strength formulation was prepared containing 270 g/L of metconazole by dissolving 270 g/L metconazole into 600 g/L N,N-dimethyldecanamide under gentle heating to 40°C and stirring until metconazole is completely dissolved.
- 106 g/L of emulsifier EO-PO block copolymer blend under stirring and slow cooling down of the formulation.
- the prepared formulation remained stable with appearance unchanged after post-accelerated storage for two weeks at 54°C ⁇ 2°C.
- Formulation according to Example 1 was also tested in the field trial in wheat against Puccinia to confirm the efficacy as well as the absence of negative effects.
- FL-1 , FL-2, FL-n, etc. - means flag leaf minus 1 , flag leaf minus 2, flag leaf minus n, wherein leaf-n is the oldest leaf on the plant (first emerged) FLAGLE - means flag leaf
- Formulation applied in the treatment was prepared by dilution with water of formulation according to Example 1 to predetermined concentration according to the table below.
- Obtained results show pest severity as percentage (%) of leaf that has disease for the row in the table marked as UNTREATED, wherein control of the disease is shown as percentage (%) of control in rows wherein treatments were applied.
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- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
L'invention concerne des compositions fongicides stables comprenant du metconazole.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP21191211.8 | 2021-08-13 | ||
| EP21191211 | 2021-08-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2023017167A1 true WO2023017167A1 (fr) | 2023-02-16 |
Family
ID=77338512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2022/072709 WO2023017167A1 (fr) | 2021-08-13 | 2022-08-12 | Compositions fongicides de metconazole |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2023017167A1 (fr) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0453899A1 (fr) * | 1990-04-27 | 1991-10-30 | Bayer Ag | Utilisation de diméthyl-amides alkylcarboxyliques comme inhibiteurs de cristallisation |
| EP1023837A2 (fr) * | 1999-01-29 | 2000-08-02 | American Cyanamid Company | Concentré émulsifiable non aqueux |
| WO2008069822A1 (fr) * | 2006-02-21 | 2008-06-12 | Phibro-Tech Inc. | Concentrés d'émulsions d'azoles biocides ayant une teneur en ingrédient actif élevée |
| JP2016145177A (ja) * | 2015-02-09 | 2016-08-12 | 株式会社クレハ | 農園芸用乳剤およびその調製方法 |
| WO2021099350A1 (fr) * | 2019-11-18 | 2021-05-27 | Life Scientific Ltd | Composition comprenant des fongicides de type azole et des amides d'acides gras |
-
2022
- 2022-08-12 WO PCT/EP2022/072709 patent/WO2023017167A1/fr unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0453899A1 (fr) * | 1990-04-27 | 1991-10-30 | Bayer Ag | Utilisation de diméthyl-amides alkylcarboxyliques comme inhibiteurs de cristallisation |
| EP1023837A2 (fr) * | 1999-01-29 | 2000-08-02 | American Cyanamid Company | Concentré émulsifiable non aqueux |
| WO2008069822A1 (fr) * | 2006-02-21 | 2008-06-12 | Phibro-Tech Inc. | Concentrés d'émulsions d'azoles biocides ayant une teneur en ingrédient actif élevée |
| JP2016145177A (ja) * | 2015-02-09 | 2016-08-12 | 株式会社クレハ | 農園芸用乳剤およびその調製方法 |
| WO2021099350A1 (fr) * | 2019-11-18 | 2021-05-27 | Life Scientific Ltd | Composition comprenant des fongicides de type azole et des amides d'acides gras |
Non-Patent Citations (1)
| Title |
|---|
| DA SILVA ARDUIM GISELE ET AL: "In vivo sensitivity reduction of Puccinia triticina races, causal agent of wheat leaf rust, to DMI and QoI fungicides", SUMMA PHYTOPATHOLOGICA, vol. 38, no. 4, 1 January 2012 (2012-01-01), pages 306 - 311, XP055977647, Retrieved from the Internet <URL:https://www.scielo.br/j/sp/a/88tWCq64RhYYLYFgLhzbXcR/?format=pdf&lang=en> * |
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