WO2021099350A1 - Composition comprenant des fongicides de type azole et des amides d'acides gras - Google Patents

Composition comprenant des fongicides de type azole et des amides d'acides gras Download PDF

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WO2021099350A1
WO2021099350A1 PCT/EP2020/082476 EP2020082476W WO2021099350A1 WO 2021099350 A1 WO2021099350 A1 WO 2021099350A1 EP 2020082476 W EP2020082476 W EP 2020082476W WO 2021099350 A1 WO2021099350 A1 WO 2021099350A1
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composition
azole fungicide
fatty acid
proportion
prothioconazole
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PCT/EP2020/082476
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English (en)
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Paul O'byrne
Robert Williams
Eugene MAHON
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Life Scientific Ltd
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    • 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 technology generally relates to a plant protection composition
  • a plant protection composition comprising at least one azole fungicide, and at least one fatty acid amide, more specifically the fatty acid of the fatty acid amide being derived from a vegetable oil.
  • An object of the present technology is to provide an improved fungicidal composition with increased penetration abilities, and therefore improved efficiency in killing fungi infecting plants.
  • the present technology relates to a fungicidal composition.
  • the fungicidal composition comprises at least one azole fungicide, and at least one fatty acid amide of formula R1-CO-NR2R3, wherein R1 is a fatty acid derived from a vegetable oil, and R2 and R3 are independently a methyl or an ethyl.
  • the present technology relates to an emulsion obtained by mixing said fungicidal composition with a diluent.
  • the present technology relates to a method for improving the penetration of at least one azole fungicide into a plant. The method comprises applying any one or more of said composition and said emulsion, to a plant.
  • the present technology relates to the use of any one or more of said composition, and said emulsion in the protection or treatment of a plant in need thereof.
  • the present technology relates to a method for controlling one or more harmful fungus comprising contacting the harmful fungus, a habitat thereof, a host thereof, optionally plants, and/or seed, and/or soil, an area and an environment in which plants grow or could grow, and/or materials, plants, seeds, soil, surfaces, and/or spaces which are to be protected from attack or infestation by one or more fungus that are harmful to plants, with an effective amount of any one or more of said composition or said emulsion.
  • Embodiments of the presently described fungicidal composition facilitate the penetration of azole fungicides into plants and thereby improve their efficiency.
  • FIG. 1 illustrates a comparison of % radiolabelled prothioconazole cuticle penetration in a composition comprising tall oil fatty acid dimethylamide (E593B) and N,N- dimethyldecanamide (E597A).
  • FIG. 2 illustrates a comparison of % radiolabelled prothioconazole cuticle penetration of a prothioconazole: tebuconazole composition comprising tall oil fatty acid dimethylamide (E597C) and N,N-dimethyldecanamide (E597B).
  • FIG. 4 illustrates a comparison of the % radiolabelled prothioconazole in plant in a composition comprising tall oil fatty acid dimethylamide (E600D) and N,N-dimethyldecanamide (E600C).
  • the term “and/or” is to be taken as specific disclosure of each of the two specified features or components with or without the other.
  • a and/or B is to be taken as specific disclosure of each of (i) A, (ii) B and (iii) A and B, just as if each is set out individually herein.
  • composition as used interchangeably herein are equivalent terms referring to a composition of matter.
  • plant-protection composition refers to a composition to be applied on plants protecting them against the harmful effect of a stress.
  • fungicide refers to a substance that destroys or controls growth of fungus.
  • azole refers to a class of five-membered heterocyclic compounds containing a nitrogen atom and at least one other non-carbon atom (i.e. nitrogen, sulfur, or oxygen) as part of the ring.
  • fatty acid refers to a carboxylic acid with a long aliphatic chain, having more than 4 Carbon atoms in the aliphatic chain, which is either saturated or unsaturated.
  • Fatty acids having more than 4 Carbon atoms in the aliphatic chain include fatty acids having more than 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 Carbon atoms, or at least 18 Carbon atoms.
  • emulsion refers to a mixture of two or more liquids that are normally immiscible.
  • the term “protection” refers to protecting plants from harmful organisms, including harmful fungi.
  • the term “treatment” refers to controlling the growth and spread of diseases caused by harmful organisms in a plant, including phytopathogenic fungi.
  • the present technology is related to a composition comprising at least one azole fungicide, and at least one fatty acid amide.
  • alkyl carboxylic acid dimethylamides and more specifically C5-C19 fatty acid amides, have been used to inhibit the crystallization of azole fungicides (US Patent No. 5,206,225, Horstmann et al., incorporated herein by reference), which otherwise block the filters and nozzles of spray equipment used for the application of plant treatment agents.
  • Rochling et al. US Patent No.
  • N,N-dimethyl-n-hexanamide, N,N-dimethyl-n-octanamide, N,N-dimethyl-n-decanamide and N,N-dimethyl-n-dodecanamide in particular N,N-dimethyl-n- octanamide and N,N-dimethyl-n-decanamide to increase the penetration of agrochemical active substances, including azole fungicides, across the cuticle of a plant to increase the biological activity of plant protection compositions.
  • compositions comprising azole fungicides and fatty acid amides have also been described in WO 94/13140, US 2008/262061, EP 3 178 320, US Patent No. 4,713,184, WO 99/02037, WO 93/01801, and US Patent No. 3, 199, 989 (all incorporated herein by reference).
  • the inventors of the present technology have discovered that N,N-dimethylamides of fatty acids derived from vegetable oils are advantageous over those described in the documents cited above and increase the foliar penetration of azole fungicides, and therefore, by inference, the biological activity of these plant protection compositions. More specifically, the inventors have discovered that tall oil fatty acid dimethylamides improve the effectiveness of azole fungicides.
  • Non-limiting examples of azole fungicides suitable for use in the composition of the present technology include 5-chloro-3-methyl-4-nitro-1H-pyrazole (CMNP); azaconazole; bromuconazole; chlorfenazole; cyproconazole; difenoconazole; diniconazole; dinicon-azole-M; epoxiconazole; enilconazole; etaconazole; etridiazole; fenbuconazole; fluquinconazole; flusilazole; fuberidazole; hexaconazole; imibenconazole; ipfentrifluconazole; ipconazole; mefentrifluconazole; metconazole; oxpoconazole; penconazole; probenazole; propiconazole; prothioconazole; quinconazole; simeconazole; tebuconazole; t
  • the composition of the present technology may comprise a combination of azole fungicides.
  • the composition of the present technology may comprise a first azole fungicide and a second azole fungicide.
  • the first azole fungicide is prothioconazole with a second azole fungicide, particularly as listed above.
  • the first azole fungicide is prothioconazole and the second azole fungicide is tebuconazole or metconazole.
  • the proportion of the first azole fungicide to the second azole fungicide as defined above may be between about 10: 1 to about 1:10, between about 5 : 1 to about 1:5, between about 2:1 to about 1:3, between about 1:1 to about 1:2, or between about 1:6 to about 1:8, between about 2:1 to about 1:9, between about 2:1 to about 1:8, between about 2:1 to about 1:7, between about 2:1 to about 1:6, between about 2:1 to about 1:5, between about 2:1 to about 1:4, between about 2:1 to about 1:3, between about 2:1 to about 1:2,.
  • the proportion of the first azole fungicide to the second azole fungicide is 1:1.
  • the proportion of the first azole fungicide to the second azole fungicide as defined above is between 3:1 to 1:2.
  • the composition may contain with the azole fungicides, alone or a mixture of azole fungicides as defined above, one or more non-azole fungicidal active ingredients.
  • non-azole fungicides are known in the art, eventually for their use in combination with one or more azole fungicides.
  • Non-limiting examples of other fungicides include 2-phenylphenol; 8-hydroxyquinoline sulphate; acibenzolar-S-methyl; aldimorph; amidoflumet; ampropylfos; ampropylfos-potassium; andoprim; anilazine; azoxystrobin; benalaxyl; benalaxyl-M; benodanil; benomyl; benthiavalicarb-isopropyl; benzamacril; benzamacril-isobutyl; benzovindiflupyr; bilanafos; bina-pacryl; biphenyl; bitertanol; bixafen; blasticidin-S; boscalid; bupirimate; buthiobate; butylamine; calcium polysulphide; capsimycin; captafol; captan; carbendazim; carboxin; carpropamid; carvone; quinom
  • Preferred non-azole fungicides used in combination with the azole fungicides are particularly selected among isopyrazam, spiroxamine, bifaxen, fluopyram, benzovindiflypyr, fluoxastrobin, trifloxystrobin and mixtures thereof.
  • the fatty acid amide used in the composition of the present technology is of formula R1-CO-NR2R3, wherein R1 is a fatty acid derived from a vegetable oil, and R2 and R3 are independently a methyl or an ethyl.
  • R1 may be an unbranched or branched, saturated or unsaturated fatty acid.
  • R1 may be an unbranched and unsaturated alkyl group having 14 to 22 carbon atoms.
  • R1 may be an unbranched and unsaturated alkyl group having 18 carbon atoms.
  • the fatty acid in the fatty acid amide is derived from a vegetable oil.
  • fatty acid amide derived from vegetable oils it is meant that the components of the fatty acids of the natural vegetable oil have been modified to have the structure of R1-CO-NR2R3 as described above.
  • at least 50 percent of the fatty acids present in the vegetable oil may be modified to have the structure of R1-CO-NR2R3. More preferably, at least 95 percent of the fatty acids present in the vegetable oil are modified as such.
  • Non-limiting examples of vegetable oils suitable for use in the composition of the present technology include coconut oil, com oil, cottonseed oil, palm oil, soybean oil, peanut oil, canola oil, safflower oil, sunflower oil, babassu oil, castor oil, linseed oil, olive oil, tung oil and tall oil.
  • the fatty acid is derived from vegetable oils selected from the group consisting of coconut oil, com oil, cottonseed oil, palm oil, soybean oil, and tall oil.
  • the vegetable oil is tall oil. As seen in Table 1, these oils consist primarily of C16-C18 unsaturated fatty acids (>88%) (Composition and Constants of Fats and Oils, Armour Chemical Division, Chicago, Illinois).
  • tall oil may also comprise a percentage of other acids and saponifiable matter (Heterogeneous Acid-Catalyzed Biodiesel Production from Crude Tall Oil: A Low-Grade and Less Expensive Feedstock. Journal of Wood Chemistry and Technology 35(5), 374-385) (Table 2).
  • Table 2 Heterogeneous Acid-Catalyzed Biodiesel Production from Crude Tall Oil: A Low-Grade and Less Expensive Feedstock. Journal of Wood Chemistry and Technology 35(5), 374-385) (Table 2).
  • the fatty acid derived from any one or more of the vegetable oils listed above may comprise at least one of Why, Myristic, Palmitic, Stearic, Lauroleic, Myristoleic, palmitoleic, Oleic, and Linoleic acid.
  • N,N-dimethylamide tall oil fatty acids are commercially available and sold as DMATO on the market.
  • N,N-dimethylamide tall oil fatty acids are also available in compositions wherein the N,N-dimethylamide tall oil fatty acids are diluted with alcohol ethoxylate, and sold as DMAD.
  • DMAD the alcohol ethoxylate used to dilute the N,N- dimethylamide tall oil fatty acids consist of, C9-11-iso-C10-rich, ethoxylated in DMAD.
  • the proportion of tall oil to alcohol ethoxylate may be between about 50:50 and about 90:10 , between about 50:50 and about 80:20, between about 50:50 and about 70:30, between about 50:50 and about 60:40, between about 60:40 and about 90:10, between about 60:40 and about 80:20, between about 60:40 and about 70:30, between about 70:30 and about
  • the proportion of the at least one azole fungicide to the fatty acid amide of formula R1-CO-NR2R3 defined above is between about 1:1 to about 1:15, between about 1 :2 to about 1 :4, between about 1 :4 to about 1 :6, between about 1 :6 to about 1:8, between about 1:8 to about 1:15, between about 1:1 to about 1:2.5, preferably between about 1:1.5 to about 1:2, and more preferably about 1:2.
  • the amount of azole fungicide in these proportions are based on the total amount of azole fungicides, alone or in mixtures as defined above.
  • the total proportion of the non-azole fungicidal active ingredient in the composition may be between about 5 %w/w to about 35 %w/w of the total composition, particularly from 7.5 %w/w to 30% w/w, and more particularly from 10% w/w to 20% w/w.
  • the proportion of at least one fatty acid amide in the composition of the present technology is between about 20 %w/w to about 90 %w/w of the total composition, particularly from 25 %w/w to 75% w/w, more particularly from 25 % w/w to 60% w/w, and preferably from 40 %w/w to 60% w/w. .
  • composition of the present technology may further comprise at least one additive selected from emulsifiers, defoamers, thickeners, dispersants, stabilizers, suspending agents, adjuvants, preservatives, polymers, acids, bases, dyes, antifreezes, biocides, fillers, wetting agents, solvents and water.
  • additives selected from emulsifiers, defoamers, thickeners, dispersants, stabilizers, suspending agents, adjuvants, preservatives, polymers, acids, bases, dyes, antifreezes, biocides, fillers, wetting agents, solvents and water.
  • Non-limiting examples of non-ionic emulsifiers suitable for the composition of the present technology include polyoxyalkylene alkyl ethers such as polyoxyethylene alkyl ethers (e.g., polyoxyethylene oleyl ether), polyoxyalkylene alkyl aryl ethers such as polyoxyethylene alkyl phenol, a polyoxyalkylene alkyl aryl ether/formaldehyde condensate, polyoxyalkylene aryl ether, polyoxyalkylene alkyl ester, polyoxyalkylene alkyl sorbitol ester, polyoxyalkylene sorbitan ester, polyoxyalkylene alkyl glycerol ester, polyoxyalkylene block copolymers (e.g., those containing a polyoxypropylene group), polyoxyalkylene block copolymer alkyl glycerol ester, polyoxyalkylene alkyl sulfonamide, polyoxyalkylene ros
  • the non-ionic emulsifier may be any one or more of Emulsogen EL-300 and Soprophor® 796/P.
  • Solvesso® 200 calcium dodecylbenzenesulphonate such as Rhodocal® 70/B (Rhodia), Phenyl sulfonate CA100 (Clariant GmbH) or isopropyl ammonium dodecylbenzenesulphonates such as Atlox® 3300B (Uniqema).
  • the emulsifier may also act as a dispersant and/or wetting agent.
  • the emulsifier is Soprophor 796/P.
  • Suitable defoamers are all substances which can typically be used for this purpose in agrochemicals. Preference is given to silicone oils, silicone oil formulations, magnesium stearate, phosphinic acids and phosphonic acids. Examples are Silcolapse® 482 from Bluestar Silicones, Silfoam® SC1132 from Wacker [dimethylsiloxanes and -silicones, CAS No. 63148- 62-9], SAG 1538 or SAG 1572 from Momentive [dimethylsiloxanes and -silicones, CAS-Nr. 63148-62-9] or Fluowet® PL 80.
  • any one or more of the substances listed above may additionally act as a dispersant, wetting, or suspending agent.
  • Non-limiting examples of such substances include non-ionic phenol ethoxylates such as Soprophor 796/P and Genapol ID 60.
  • additional dispersant, defoamer, wetting, and suspending agent may be incorporated in the composition of the present technology. Suitable substances are all of those which can typically be used for this purpose in agrochemicals, and are well-known in the arts.
  • the composition of the present technology may comprise surfactants or esters of fatty acids.
  • Non-limiting examples of surfactants suitable for the composition of the present technology include Plurafac SL-42, Lutensol XL-40, Ecosurf EH-3, Surfonic PEA-25, X-AES, Alfoterra 123-4S, Marlowet 4561, sodium lauryl ether sulfate, ethoxylated alcohol surfactants (e.g. , Tomadol 25-3, Tomadol 25-7), fatty acid diethanolamine (e.g., cocamide DEA), orange oil emulsifier (e.g. , Videt ME-80), acrylate-based emulsion copolymer (e.g.
  • Alcogum SL-70 polyoxyethers of lauryl alcohol (e.g., Laureth-7), linear isopropylamine dodecylbenzene sulfonate (e.g., Rhodocal IP AM), blended alcohol ethoxylate (e.g., Videt Q3), alkoxylated alcohol (e.g. , Tergitol 15-S-7), sodium iminodipropionate (e.g., Amphoteric 400), nonionic alcohol ethoxylates (e.g., Ecosurf EH-6), a palm kernel alcohol ethoxylated and propoxylated surfactant (e.g.
  • lauryl alcohol e.g., Laureth-7
  • linear isopropylamine dodecylbenzene sulfonate e.g., Rhodocal IP AM
  • blended alcohol ethoxylate e.g., Videt Q3
  • alkoxylated alcohol e.g
  • the composition of the invention comprises at least an azole fungicide 5 to 30 %w/w particularly prothioconazole (alone or with tebuconazole), R1-CO-NR2R3, particularly amide of tall oil 20 to 60 % w/w emulsifier, particularly castor oil ethoxylate 10 to 30 %w/w emulsifier, particularly non-ionic fatty alcohol alkoxylates 2 to 10 % w/w
  • the present technology relates to an emulsion obtainable by mixing the composition described herein with a diluent.
  • the diluent may be water.
  • the composition of the present technology can be diluted such that the final concentration of azole fungicide, alone or in mixtures as described above, in the emulsion would be between about 0.25 g/L and about 3g/L, between about 0. 5g/L and about 2.5g/L, between about 0.75g/L and about 2.25g/L, between about 0.75g/L and about 2.15 g/L.
  • the present technology relates to an emulsion obtainable by mixing extemporaneously and separately the components of the composition described herein with the diluent.
  • the proportions of the components and the diluent are such that the same amount of azole fungicides and amide of formula R1-CO-NR2R3, particularly amide of tall oil, are present in the emulsion as defined above.
  • the present technology relates to a method for improving the penetration of at least one azole fungicide into a plant comprising applying any one or more of various embodiments of the composition or emulsion described herein to said plant by spraying, painting or direct application on the leaves using a dropper, and the like.
  • the present technology relates to the use of any one or more of embodiments of the composition or emulsion described herein in the protection or treatment of a plant in need thereof.
  • Plants which can be protected or treated with the composition of the present technology include but are not limited to cereals such as wheat, barley, rye, oats, millet, rice, cassava and maize, or crops of peanuts, sugar beet, cotton, soybeans, oilseed rape, potatoes, tomatoes, peas and other vegetables, useful plants and ornamental plants in gardens and forests; and genetically modified varieties of each of these plants, and the seeds of these plants.
  • the treatment may be applied separately or together with one or more other agrochemical active substances.
  • agrochemical active substances include but are not limited to bactericides, insecticides, acaridices, nematicides, herbicides, as well as other fungicides different from azole fungicides particularly those defined above.
  • the one or more agrochemical active substance may be added to the emulsion as described above.
  • the present technology further comprises a tank mix comprising the composition of the invention with a diluent and at least one other agrochemical active substances.
  • composition or emulsion of the present technology may be applied as an aqueous spray mixture on the leaves of the plant but may also be applied to the seed, the soil, any area and environment in which plants grow or could grow, and/or materials, plants, seeds, soil, surfaces, and/or spaces which are to be protected from attack or infestation by one or more fungus that are harmful to plants.
  • the invention also comprises a method for protecting or treating a plant in need thereof, particularly for controlling fungal infection in said plant, comprising the steps of (i) preparing a tank mix comprising at least one azole fungicide, alone or in a mixture with another azole fungicide, and at least one fatty acid amide of formula R1-CO-NR2R3, optionally adding at least another pest control agent, particularly another non-azole fungicide, and a solvent, and (ii) applying the tank mix to the plants.
  • azole fungicides their mixtures, fatty acid amides, other pest control agents, solvents and proportion thereof are as defined above in all their combinations.
  • Azole fungicide(s), fatty acid amide(s), solvent and optional other pest control agent may be added in any suitable order for the preparation of the tank mix.
  • the tank mix is prepared in adding a composition of the invention to the solvent.
  • the tank mix is prepared in adding the azole fungicide to a mixture of solvent and fatty acid amide.
  • the tank mix is prepared in adding the fatty acid amide to a mixture of solvent and azole fungicide. Etc.
  • Example 1 Preparation of prothioconazole containing emulsifiable concentrate formulations
  • DMAD is a 9:1 mixture of N,N-dimethylamides of tail-oil fatty acids (EC: 269-665-4, CAS: 68308-74-7), and Alcohols (C9-11-iso-, C10-rich, ethoxylated, CAS: 78330-20-8).
  • compositions were prepared by mixing additional azole fungicides and other additives in the composition. Detailed recipes for these compositions are shown in Table 4.
  • Example 3 Active leaf cuticle penetration test of radiolabelled compositions comprising tail-oil fatty acid dimethylamides, and comparison with equivalent compositions comprising N,N-dimethyldecanamide.
  • composition E593B and E597A (as described in Table 3) were used at 1 g/L of active ingredient (a.i.), and E597B and E597C (as described in Table 4) used at 0.5 g/L a.i..
  • Radiolabelled 14C-prothioconazole was obtained from Izotop, Budapest, Hungary. Radiolabel incorporation and solution homogeneity were confirmed by sampling multiple aliquots and quantifying radioactivity prior to use. The radioactive mass constituted approx. 10% of the total a.i. in solution.
  • Prothioconazole penetration was studied after applying the radio labelled treatments to the outer surface of cuticles and measuring their appearance in a receiver solution in contact with the inner surface.
  • Treatments E593B and E597A were compared together in a single study; treatments E597B and E597C were then compared in a second study.
  • Treatments were applied to dry cuticles and left to dry before the penetration chambers were inverted.
  • a syringe was used to fill the chambers through the sampling port. The ports were sealed, and the chambers were transported to a controlled environment and agitated gently and continuously on an orbital shaker for 48 h.
  • the quantity of radiolabelled prothioconazole applied to cuticles in each treatment was determined by dispensing the standard application volume directly into scintillation vials at the time of treatment.
  • the receiver solution was sampled at six-time intervals after the solution was added; at 0, 3, 6, 9, 24 and 48 h after treatment. At each sampling period, an aliquot of the receiver solution was withdrawn quantitatively and replaced by fresh PSL. Radioactivity in the sampled receiver solution was determined by adding scintillant cocktail to each sample and assaying using a liquid scintillation counter. At the end of the experiment, the exposed cuticles were sampled and stored frozen in case needed to determine residual radioactivity associated with the cuticle. The amount of prothioconazole from each treatment penetrating at time intervals was calculated by summation, as a percentage of the total radiolabelled fungicide applied. Experiments were subjected to analysis of variance and least significant difference tests were used to compare treatments. Stabilising transformations were performed as necessary, prior to analysis.
  • the sample size was 10 cuticles per treatment, but cuticle failures due to fragility and breakage during the studies reduced this to 8-9 replicates per treatment.
  • compositions were prepared by mixing 250 g of Prothioconazole, with a mixture of tristyrylphenol ethoxylate, ethylenediamine alkoxylate, alcohols ethoxylated propoxylated, a tristyrylphenol ethoxylate propoxylate and DMAD comprising N,N-dimethylamides of tail-oil fatty acids (CAS: 68308-74-7) and alcohol ethoxylate or N,N-dimethyldecanamide (CAS No. 14433-76-2) and alcohol ethoxylate respectively (Table 6). The mixtures were stirred until all the Prothioconazole was dissolved and a clear solution was obtained. Table 6 Preparation of E600C and E600D
  • Example 5 Plant uptake test of compositions comprising tail-oil fatty acid dimethylamides, and comparison with equivalent compositions comprising N,N, dimethyldecanamide.
  • Winter barley plants were cultivated under glass, ensuring applied treatments would not conflict with the active substance to be measured. The plants were transported to the test site, watered and allowed to recover for 24 hours before application. The average height of the plants was around 30 cm with 3 or more tillers. The spray boom was set up to ensure an application from a height of 0.5 m above the plant canopy. Each composition was applied using three conventional flat fan nozzles which were mounted on a boom, attached to a track sprayer. Leaf surfaces were completely dry at the time of application. The application parameters used in this study are detailed in Table 7.
  • Table 7 Application parameters [0083] Plants were arranged in rows of 3 plants across the boom width, with up to 6 rows for one application. Each composition was mixed immediately prior to application using CIPAC D water. The compositions were thoroughly combined with the water using a magnetic stirrer before transferring to the Cornelius can for application. Care was also taken to thoroughly wash the Cornelius canisters and spray lines between each composition used to prevent cross contamination. Samples of the tank mix were taken from the nozzle and stored in case required for confirmation of concentration.
  • each set of plants was allowed to dry before destructively sampling the plants at each of the 5 timings.
  • the relative amount of a.i. taken up into the plant at each timing was assessed by: I) extraction of material deposited on the external plant surfaces into a solvent mixture; and II) measurement of the active substance within the remaining plant material.
  • Example 6 Plant uptake test of compositions comprising tail-oil fatty acid dimethylamides, and comparison with equivalent compositions comprising N,N- dimethyldecanamide. [0087] This study determined the comparative uptake of two radiolabelled prothioconazole treatments, into barley ( Hordeum vulgare ) foliage, over a 48 h period.
  • Barley seeds (Hordeum vulgare) were germinated and grown individually in pots in a controlled environment simulating spring conditions to the stage of tiller formation. They were treated at approximately 4 weeks old.
  • Two prothioconazole formulations were assessed, E600C and E600D (all 250 g/L prothioconazole) used at 1 g/L a.i. (0.8 kg formulation/200 L/ha application).
  • Radiolabelled 14C-prothioconazole was obtained from Izotop, Budapest, Hungary. Radiolabelled prothioconazole in acetonitrile was dispensed into micro-vials and blown down to dryness. Prothioconazole treatments were pre-warmed in a water bath, appropriate aliquots of each formulation were added on top of the radiolabelled a.i. and the micro-vial contents were sonicated. Appropriate water volumes were then added to the micro-vials to dilute each treatment to the required concentration (0.8 kg/200 L). Radiolabel incorporation and solution homogeneity were confirmed by sampling multiple aliquots and quantifying radioactivity prior to use.
  • Treatments were applied to the central region on the adaxial surface of the youngest fully expanded leaf on each plant (5 replicates per treatment). Droplets (30x0.24 ⁇ l) were applied by micro syringe with a repeating dispenser, simulating an application volume of 200 L/ha (2 ⁇ l/cm 2 ). The quantity of radiolabelled prothioconazole applied to replicate leaves in each treatment was determined by dispensing the standard application volume directly into scintillation vials (4 replicates) at the time of treatment. Plants were allocated to treatments using a completely randomised design.
  • Uptake of radiolabel into the plant was determined at five intervals after treatment; 0, 3, 6, 24 and 48 h. This was assessed by washing the treated leaf to recover unabsorbed radiolabel. The washings were taken up in ACS scintillant solution and the radioactivity quantified by liquid scintillation counting. The 0 h recovery was performed at 10 mins after treatment and recovered > 99% of applied radioactivity for all treatments.

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  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne une composition phytosanitaire comprenant au moins un fongicide de type azole, et au moins un amide d'acide gras de formule R1-CO-NR2R3, dans laquelle R1 est un acide gras dérivé d'une huile végétale, et R2 et R3 sont indépendamment un méthyle ou un éthyle.
PCT/EP2020/082476 2019-11-18 2020-11-18 Composition comprenant des fongicides de type azole et des amides d'acides gras WO2021099350A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023017167A1 (fr) * 2021-08-13 2023-02-16 Globachem Nv Compositions fongicides de metconazole

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3199989A (en) 1962-07-16 1965-08-10 Stanley J Buckman Corrosion inhibitor and method of using the same
US4713184A (en) 1985-09-26 1987-12-15 Zaid Najib H Dispersed oil soluble corrosion inhibitor and water soluble phosphonate scale inhibitor composition
WO1993001801A1 (fr) 1991-07-25 1993-02-04 Micro Vesicular Systems, Inc. Vesicules lipidiques renfermant des derives n, n-dimethylamides en tant que lipides primaires
US5206225A (en) 1990-04-27 1993-04-27 Bayer Aktiengesellschaft Alkylcarboxylic acid dimethylamides as crystallization inhibitors
WO1994013140A1 (fr) 1992-12-14 1994-06-23 Buckman Laboratories International, Inc. Composition et procede augmentant l'efficacite des pesticides
WO1999002037A1 (fr) 1997-07-11 1999-01-21 Buckman Laboratories International, Inc. Compositions antimicrobiennes synergiques contenant un dimethylamide d'acide carboxylique associe a un melange de 2-(thiocyanomethylthio) benzothiazole et de methylene-bis(thiocyanate)
US20070293550A1 (en) * 2004-04-27 2007-12-20 Bayer Cropscience Aktiengesellschaft Use of Alkyl Carboxylic Acid Amides as Penetration Enhancers
US20080262061A1 (en) 2007-04-18 2008-10-23 Helena Holding Company Composition and use of a liquid fungicidal formulation of myclobutanil or tebuconazole fungicide
EP3178320A1 (fr) 2015-12-11 2017-06-14 Bayer CropScience AG Formules liquides contenant un fongicide

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3199989A (en) 1962-07-16 1965-08-10 Stanley J Buckman Corrosion inhibitor and method of using the same
US4713184A (en) 1985-09-26 1987-12-15 Zaid Najib H Dispersed oil soluble corrosion inhibitor and water soluble phosphonate scale inhibitor composition
US5206225A (en) 1990-04-27 1993-04-27 Bayer Aktiengesellschaft Alkylcarboxylic acid dimethylamides as crystallization inhibitors
WO1993001801A1 (fr) 1991-07-25 1993-02-04 Micro Vesicular Systems, Inc. Vesicules lipidiques renfermant des derives n, n-dimethylamides en tant que lipides primaires
WO1994013140A1 (fr) 1992-12-14 1994-06-23 Buckman Laboratories International, Inc. Composition et procede augmentant l'efficacite des pesticides
WO1999002037A1 (fr) 1997-07-11 1999-01-21 Buckman Laboratories International, Inc. Compositions antimicrobiennes synergiques contenant un dimethylamide d'acide carboxylique associe a un melange de 2-(thiocyanomethylthio) benzothiazole et de methylene-bis(thiocyanate)
US20070293550A1 (en) * 2004-04-27 2007-12-20 Bayer Cropscience Aktiengesellschaft Use of Alkyl Carboxylic Acid Amides as Penetration Enhancers
US8124564B2 (en) 2004-04-27 2012-02-28 Bayer Cropscience Ag Use of alkyl carboxylic acid amides as penetration enhancers
US20080262061A1 (en) 2007-04-18 2008-10-23 Helena Holding Company Composition and use of a liquid fungicidal formulation of myclobutanil or tebuconazole fungicide
EP3178320A1 (fr) 2015-12-11 2017-06-14 Bayer CropScience AG Formules liquides contenant un fongicide

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
"Heterogeneous Acid-Catalyzed Biodiesel Production from Crude Tall Oil: A Low-Grade and Less Expensive Feedstock", JOURNAL OF WOOD CHEMISTRY AND TECHNOLOGY, vol. 35, no. 5, pages 374 - 385
CAS, no. 78330-20-8

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023017167A1 (fr) * 2021-08-13 2023-02-16 Globachem Nv Compositions fongicides de metconazole

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