GB1561634A - Fungicidal compositions - Google Patents

Fungicidal compositions Download PDF

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Publication number
GB1561634A
GB1561634A GB44532/75A GB4453275A GB1561634A GB 1561634 A GB1561634 A GB 1561634A GB 44532/75 A GB44532/75 A GB 44532/75A GB 4453275 A GB4453275 A GB 4453275A GB 1561634 A GB1561634 A GB 1561634A
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United Kingdom
Prior art keywords
weight
pyrimidinemethanol
fungicidal formulation
coingredient
formulation
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.)
Expired
Application number
GB44532/75A
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.)
Lilly Industries Ltd
Original Assignee
Lilly Industries Ltd
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 Lilly Industries Ltd filed Critical Lilly Industries Ltd
Priority to GB44532/75A priority Critical patent/GB1561634A/en
Priority to IE2237/76A priority patent/IE43954B1/en
Priority to CA263,290A priority patent/CA1076024A/en
Priority to NZ182331A priority patent/NZ182331A/en
Priority to IL50688A priority patent/IL50688A/en
Priority to AU18858/76A priority patent/AU506064B2/en
Priority to ZA00766244A priority patent/ZA766244B/en
Priority to GR51999A priority patent/GR61690B/en
Priority to FR7632061A priority patent/FR2329200A1/en
Priority to CH1344376A priority patent/CH602002A5/xx
Priority to IT5189976A priority patent/IT1123020B/en
Priority to PL1976193309A priority patent/PL106521B1/en
Priority to DD195482A priority patent/DD126593A5/xx
Priority to BR7607237A priority patent/BR7607237A/en
Priority to DE19762648705 priority patent/DE2648705A1/en
Priority to AT797476A priority patent/AT353544B/en
Priority to AR265256A priority patent/AR215605A1/en
Priority to BE6045738A priority patent/BE847771A/en
Priority to BG7634549A priority patent/BG27522A3/en
Priority to CS766977A priority patent/CS189039B2/en
Priority to DK488776A priority patent/DK152661C/en
Priority to NO763677A priority patent/NO763677L/no
Priority to SU762415100A priority patent/SU730269A3/en
Priority to SE7612063A priority patent/SE430118B/en
Priority to JP51130386A priority patent/JPS5254029A/en
Priority to NLAANVRAGE7611998,A priority patent/NL188139C/en
Publication of GB1561634A publication Critical patent/GB1561634A/en
Expired legal-status Critical Current

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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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing >N—S—C≡(Hal)3 groups
    • 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
    • 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
    • A01N25/30—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 characterised by the surfactants
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-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
    • A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48

Description

(54) FUNGICIDAL COMPOSITIONS (71) We, LILLY INDUSTRIES LIMITED, a British company of Henrietta House, Henrietta Place, London, W.1., do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: This invention relates to methods of treating fungal infections of plants and also provides fungicidal formulations for use in such methods.
In United Kingdom Patent Specification No.
1,218,623 there are described inter alia a number of pyrimidinemethanols useful in controlling fungi which attach plants.
It has now been found that two of these pyrimidinemethanols, viz. a - (2 - chloro- phenyl) - a - (4 - chlorophenyl) - 5 pyrimidinemethanol (known by the generic name 'fenarimol') and a - (2 - chlorophenyl) -(4- fluorophenyl) - 5 - pyrimidinemethanol (known by the generic name 'nuarimol'), are particularly active in the control of fungi which are pathogenic to fruit such as apples.
Furthermore, it has surprisingly been discovered that these pyrimidinemethanols when used in conjunction with certain co-ingredients, as hereinafter specified, are particularly active against the organisms Uromyces phaseoli var.
typica, Vent aria inaequalis and Puccinia recondite The combinations of the invention show a synergistic effect in the control of these organisms, i.e. the fungicidal effect of the combination is greater than the additive effect of the component, as demonstrated by utilisation of the well-known "Colby-equation," see Weeds 15, 20--22 (1967). The combinations of the invention also possess value in the control of powdery mildew (Podosphaera legco- tricha).
According to one aspect of the present invention there is provided a method of treating or preventing fungal infections of plants which comprises applying to the plant a fungicidal formulation which comprises: (a) a pyrimidine methanol of formula (I):
where X is chlorine or fluorine, or a nonphytotoxic, add-addition salt thereof; (b) a co-ingredient selected from the group consisting of dodine, captan, cationic quaternized amine surfactants, fatty amine ethyloxylates, stearamidopropyldimethyl - 1? - hydroxyethylammonium nitrate, di - isobutyl cresoxy ethoxy ethyl dimethyl benzyl ammonium chloride, and di- or trimethyl C12 16- alkyl benzyl-ammonium chlorides; associated with (c) one or more non-phytotoxic carrier(s).
A preferred cationic quaternized amine surfactant is that sold as "Quaternary O". Preferred fatty amine ethoxylates are polyoxyethylene(2) soya amine (sold under the trade name "Mazeen S-2"), polyoxyethylene(2)coco amine (sold under the trade name "Mazeen C-2") and polyoxyethylene(2) mixed fatty amines (sold under the trade name "Mazeen T-22"). Di - isobutyl cresoxy ethoxy ethyl dimethylbenzyl ammonium chloride can be obtained as the material sold under the Registered Trade Mark "Hyamine 10-X".Preferred examples of di- or trimethyl C12 lssalkyl benzyl ammonium chlorides are methyl dodecylbenzyl trimethyl ammonium chloride, methyl dodecyl xylene bis(trimethyl ammonium chloride)-sold under the trade name "Hyamine 2389"-and N-C12.14.iaalkyl dimethylbenzyl ammonium chloride (sold under the trade name "Hyamine 3500).
The above materials are all known compounds which are described in the literature, see for instance, Detergents and Ernulsifiers 1975 Annual, published by McCutcheon's Division, MC Publishing Company, U.S.A.
Stearamidopropyldimethyl - (3 - llydroxyethyl- ammonium nitrate is obtainable under the trade name "Catanac SN" from the American Cyanamid Company. Dodine (n - dodecyl guanidine) and its salts and captan [3a,4,7,7atetrahydro - N - (trichloromethanesulphenyl)phthalimide] are well-known fungicides which may be used to treat fungal infections of a number of food crops including apples-see for example United States Patent Specifica tions 2,553,770, 2,553,771, 2,553,776 and 2,867,562.
Use of dodine as the co-ingredient is presently preferred, especially in the form of its acetate. Captan is also extremely useful as the co-ingredient, especially when combined with the 'nuarimor.
The combination of the invention will normally be applied to the crop to be treated in such a way that from 1 to 80, preferably 10 to 80, grams per hectare of the pyrimidinemethanol and from 20 to 1,200 grams/hectare of co-ingredient are applied to the area of crop. Clearly the precise amount of active ingredients applied will vary within wide limits, being dependent on variables such as density of cultivation, species of crop and virulence of the potential or existing infection to be treated.
The method of the invention is particularly useful in connection with the treatment of apple trees to prevent or lower the incidence of scab (Venturia inaequafis). Dodine acetate is particularly effective as the co-ingredient in such a case. In such treatment the amount of pyrimidinemethanol utilised is preferably from 20 to 80 grams per hectare and the amount of co-ingredient is preferably from 400 to 1200 grams per hectare.
The pyrimidinemethanol and co-ingredient, may be applied separately or together to the apple trees and the treatments will usually be repeated at intervals of from 5 to 20 days commencing at the bud bursting stage or later and continuing up to harvest time, the actual frequency and duration of treatment being determined by the severity of the actual or expected disease. It may also be desirable in accordance with the method of the present invention to continue treatment of the dormant trees during the winter, particularly where there have been severe infection conditions.
When the pyrimidinemethanol and coingredient are applied together to plants requiring treatment, this combined treatment may be accomplished by mixing the two active ingredients in the spray tank just prior to use or more preferably the two active ingredients are formulated together in the desired proportions and this formulation is merely diluted prior to use.
In either case, the dilute aqueous formulation containing both active ingredients is novel and forms a part of this invention. Such a formulation will generally contain from 0.00005 to 0.007%, preferably 0.0005 to 0.004%, most preferably 0.001 to 0.004%, by weight of pyrimidinemethanol and from 0.001 to 0.1 ty < , preferably 0.001 to 0.06%, most pre- ferably 0.03 to 0.06, by weight of the coingredient, traces of any surfactants, inert carriers and the like, which were present in the concentrate compositions used to prepare the diluted formulation, and water to make 100%.
Preferably the diluted formulation in the case of a pyrimidine methanol/dodine combination wil contain from 0.001 to 0.005 O by weight of the former and 0.005 to 0.05% of the latter.
Although the antifungal combinations of the invention may be applied to the plant to be treated by any conventional technique, such as by spraying, dusting, dipping or drenching, it is preferable to treat the plants by spraying the above aqueous dispersion onto the plants. In this mode of treatment, it is usually sufficient for the infected or susceptible surfaces to be thoroughly wet with the liquid dispersion employed.
As stated above, the diluted formulations of the present invention may be produced by mixing the active ingredients just prior to use or by diluting a ready-prepared co-formulation of the two active ingredients. In either case, the active ingredients will usually be in the form of concentrate compositions so formulated as to be capable of ready dispersion or dilution in water.
In the case where the active ingredients are separately formulated, the dodine or captan components may be used in their normal commercially available forms, e.g. the dodine may be in the form of a 65% or 80% wettable powder or 20% or 25% aqueous suspension whilst the captain may be in the form of a 50% or 83% wettable powder. Similarly the pyrimidine methanol component may be formulated for example as a 4% or 10% wettable powder or as a 5 % emulsifiable concentrate. Generally however any appropriate concentrate compositions may be used and may contain from about 1 to 90% by weight of the individual active ingredients.
In the case where the active ingredients are formulated together in concentrate compositions, the latter are novel and form a part of this invention. Such concentrates may contain from 5 to 90% total weight of the active ingredients, the latter preferably being present in the weight ratio of coingredient to pyrimidine methanol of from 2: 1 to 25:1. Where a dodine/pyrimidinemethanol concentrate is concerned, the preferred ratio is 5:1 to 10:1, in each case the pyrimidine methanol most advantageously being present in an amount of 1 to 15% by weight.
The concentrate compositions of the present invention normally comprise the active ingredients in the above stated amounts, one or more inert carriers and, optionally, one or more surfactants, thickening agents, antifreezing agents and preservatives, The concentrates may be solids, usually known as wettable powders, or aqueous suspensions. When the coingredient is other than dodine or captan, the co-formulations of the present invention are preferably in the form of emulsifiable concentrates.
Wettable powders comprise an intimate mixture of the active ingredients, one or more inert carriers and appropriate surfactants. The inert carrier may, for example, be chosen from the attapulgite clays, the monunoril- lonite clays, the diatomaceous earths, kaolins, micas, talcs and purified silicates. Effective surfactants may be found among the sulfonated lignins, the naphthalene sulfonates and condensed naphthalene sulfonates, the alkyl succinates, the alkylbenzene sulfonates, the alkyl sulfates and nonionic surfactants such as ethylene oxide adducts of phenol.In general, wettable powder formulations contain from 1 to 15% by weight of pyrimidine methanol, 10 to 75% by weight of co-ingredient and 1 to 10% by weight of surfactant, a typical formulation being as follows: % by weight (a) Pyrimidine methanol 1 to 15 Coingredient 10 to 75 Surfactant(s) 1 to 10 Inert carrier to 100 Aqueous suspensions comprise the active in gredients suspended or dissolved in water to gether with any desired surfactants, thicken ing agents, antifreezing agents or preservatives. Suitable surfactants may be chosen from those mentioned above in connection with wettable powders. Thickening agents, if used, are normally chosen from appropriate cellulose materials and natural gums whilst glycols will generally be used when an antifreezing agent is required.Preservative may be chosen from a wide range of materials such as the various paraben antibacterials, phenol, o - chlorocresol, phenyl mercuric nitrate and formaldei hyde. In general, aqueous suspensions contain from 1 to 15 O by weight pyrimidine methanol, 10 to 75% by weight of co-ingredient and 0.5 to 25% by weight of surfactant(s), a typical formulation being as follows: % weight volume Pyrimidine methanol 1 to 15 Coingredient 10 to 75 Surfactant(s) 0.5 to 25 Thickening agent 0 to 3 Antifreezing agent 0 to 20 Preservative 0 to 1 Water to 100 The following non-limitative examples will further illustrate the invention.
Examples 1 to 5 illustrate the preparation of wettable powders containing the combination of the invention.
EXAMPLE 1 % by weight Fenarimol 6 Dodine acetate 30 Sodium alkyl succinate 2 Sodium lignin sulfonate 3 Silica 8 Clay to 100 EXAMPLE 2 % by weight Fenarimol 6 Dodine acetate 45 Sodium lauryl sulfate 4 Sodium lignin sulfonate 2 Kaolin to 100 EXAMPLE 3 % by weight Nuarimol 4 Dodine acetate 40 Sodium alkyl succinate 8 Mica 5 Clay to100 EXAMPLE 4 % by weight Nuarimol 3 Captan 60 Sodium lignin sulfonate 4 Sodium alkyl succinate 2 Clay to 100 EXAMPLE 5 % by weight Fenarimol 4 Dodine acetate 35 Alkaryl polyether alcohol 3 Silica 3 China clay to 100 Wettable powders were prepared having the above compositions. In each case, the active ingredients were milled and then blended with the specified exdpents in conventional mixing equipment.The blend was then further milled in a fluid energy mill to a size range of from 1 to 10 microns and finally the mixture reblended and deaerated prior to being packaged.
Examples 6 to 8 illustrate the preparation of aqueous suspensions containing the combination of the invention.
EXAMPLE 6 Aqueous % weight/ Suspensions volume Fenarimol 10 Do dine acetate 50 Sodium naphthalene sulfonate 8 Sodium lauryl sulfate 4 Gum arabic 1 o - chlorocresol 0.5 Water to 100 EXAMPLE 7 % weight/ volume Nuarimol 6 Dodine acetate 40 Sodium alkyl succinate 2 Sodium lignin sulphonate 2 Propylene glycol 8 Formaldehyde 0.2 Water to 100 EXAMPLE 8 O/o weight/ volume Fenarimol 2 Captan 40 Sodium naphthalene sulfonate 5 Sodium lignin sulfonate 8 Ethylene glycol 4 Phenol 0.5 Water to 100 Aqueous suspensions containing the components listed in Examples 6 to 8 were prepared. Both active ingredients, size reduced by conventional means, if necessary, were dispersed in water containing the surfactant system, preservative and part of the thickening agent.The particle size of both toxicants was further reduced by liquid milling, the balance of the thickening agent added, allowed to hydrate and the product diluted to volume with water.
Examples 9 and 10 illustrate the preparation of emulsifiable concentrates containing the combination of the invention.
EXAMPLE 9 % weight/ volume Fenarimol 2 Mazeen C-2* (co-ingredient) 20 Ethylene oxide/Propylene oxide block co-polymer (surfactant) 5 Dimethylnaphthalene (solvent) to 100 EXAMPLE 10 % weight/ volume Nuarimol 4 Hyamine 2389* (co ingredient) 30 Alkylaryl polyether alcohol (surfactant) 4 2 - Ethoxy ethanol (solvent) 10 Xylene (solvent) to 100 Trade name The active ingredients were added to the appropriate solvent(s) with stirring and optional heating to facilitate solubilisation of the active materials. The surfactants were then added. After solubilisation the solution was filtered to remove insoluble impurities.
EXAMPLES 11 to 17 Similar emulsifiable concentrates to that described in Example 9 were prepared by using "Quaternary O*", "Catanac SN*", "Mazeen S-2*", "Mazeen T-2*", "Hyamine 10-X*", and "Hyamine 3500*" as the coingredient *Trade name WHAT WE CLAIM IS: 1.A method of preparing a fungicidal formulation which comprises admixing: (a) a pyrimidine methanol of formula (I):
where X is chlorine or fluorine, or a nonphytotoxic, acid-addition salt thereof; (b) a co-ingredient selected from the group consisting of dodine, captan, cationic quaternized amine surfactants, fatty amine ethoxylates, stearamidopropyldimethyl - DB hydroxyethylammonium nitrate, di - isobutyl cresoxy ethoxy ethyl dimethylbenzyl ammonium chloride, and di- or trimethyl C121- alkyl benzyl-ammonium chlorides; and (c) one or more non-phytotoxic carrier(s).
2. A method according to claim 1, wherein the fungicidal formulation comprises from 5 to 9( > %, by weight of active ingredients.
3. A method according to claim 1 or 2, wherein the ratio of the coingredient to the pyrimidinemethanol is from 2:1 to 25:1 by weight 4. A method according to any one of claims 1 to 3 for preparing a wettable powder which comprises admixing from 1 to 15% by weight of the pyrimidinemethanol, from 10 to 75% by weight of the coingredient, and from 1 to 10% by weight of surfactant.
5. A method according to any one of claims 1 to 3 for preparing an aqueous suspension which comprises admixing from 1 to 15% by weight of the pyrimidinemethanol, from 10 to 75% by weight of the coingredient and from 0.5 to 25 % by weight of surfactant 6. A method according to any one of claims 1 to 5 wherein the co-ingredient is do dine acetate and the pyrimidinemethanol is fenarimol.
7. A fungicidal formulation whenever prepared by a method according to any one of

Claims (1)

  1. claims 1 to 6.
    8. A fungicidal formulation which comprises: (a) a pyrimidine methanol of formula (I):
    where X is chlorine or fluorine, or a nonphytotoxic, acid-addition salt thereof; (b) a co-ingredient selected from the group consisting of dodine, captan, cationic quaternized amine surfactants, fatty amine ethoxylates, stearamidopropyldimethyl - ss hydroxyethylammonium nitrate, di - isobutyl cresoxy ethoxy ethyl dimethylbenzyl ammonium chloride, and di- or trimethyl Cl2 1 alkyl benzyl-ammonium chlorides; associated with: (c) one or more non-phytotoxic carrier(s).
    9. A fungicidal formulation as claimed in claim 8, in the form of a dilute aqueous formulation and which comprises from 0.00005 to 0.007% by weight of the pyrimidinemethanol of formula (I) and from 0.001 to 0.1% by weight of the co-ingredient.
    10. A fungicidal formulation as claimed in claim 9, which comprises from 0.0005% to 0.004% by weight of the pyrimidinemethanol and from 0.001 to 0.6% by weight of the coingredient.
    11. A fungicidal formulation as claimed in claim 8, in the form of a concentrate and which comprises from 5 to 90% by weight of active ingredients.
    12. A fungicidal formulation as claimed in any one of claims 8 to 11, wherein the ratio of the coingredient to the pyrimidinemethanol is from 2: 1 to 25:1 by weight.
    13. A fungicidal formulation as claimed in claim 11 or 12 which is a wettable powder which comprises from 1 to 15% by weight of pyrimidinemethanol, from 10 to 75 % by weight of coingredient and from 1 to 10% by weight of surfactant.
    14. A fungicidal formulation as claimed in claim 11 or 12, which is an aqueous suspension which comprises from 1 to 15% by weight of the pyrimidinemethanol, from 10 to 75%, by weight of the co-ingredient and from 0.5 to 25% by weight of surfactant.
    15. A fungicidal formulation as claimed in any one of claims 8 to 14, wherein the pyrimidinemethanol is fenarimol and the coingredient is dodine acetate.
    16. A fungicidal formulation as claimed in claim 8, substantially as hereinbefore described with reference to any one of the foregoing Examples.
    17. A method of treating or preventing fungal infections of plants which comprises applying to the plant a fungicidal formulation as claimed in claim 8, 9 or 10.
    18. A method according to claim 17 for treating or preventing fungal infection caused by one or more organisms selected from the group consisting of Uromyces phaseoli var.
    typica, Venturia inoequalis and Puccinia recondita.
    19. A method according to claim 17 or 18 for treating or preventing fungal infections of apples.
    20. A method according to any one of claims 17 to 19 wherein the pyrimidinemethanol is fenarimol and the coingredient is dodine acetate.
GB44532/75A 1975-10-29 1975-10-29 Fungicidal compositions Expired GB1561634A (en)

Priority Applications (26)

Application Number Priority Date Filing Date Title
GB44532/75A GB1561634A (en) 1975-10-29 1975-10-29 Fungicidal compositions
IE2237/76A IE43954B1 (en) 1975-10-29 1976-10-11 Fungicidal compositions
CA263,290A CA1076024A (en) 1975-10-29 1976-10-13 Fungicidal compositions
NZ182331A NZ182331A (en) 1975-10-29 1976-10-14 Fungicidal formulations containin an -(2-chlorophenyl)- -(4-chloro(or fluoro)-phenyl)-5-pyrimidinyl-methanol
IL50688A IL50688A (en) 1975-10-29 1976-10-15 Method and compositions for treating fungal infections of plants containing ,2 bis halophenyl pyrimidinemethanol
AU18858/76A AU506064B2 (en) 1975-10-29 1976-10-20 Pyrimidinemethanol fungicidal compositions
ZA00766244A ZA766244B (en) 1975-10-29 1976-10-20 Fungicidal compositions
GR51999A GR61690B (en) 1975-10-29 1976-10-23 Fungicidal compositions
FR7632061A FR2329200A1 (en) 1975-10-29 1976-10-25 PROCESS FOR TREATING FUNGAL INFECTIONS OF PLANTS AND FUNGICIDAL COMPOSITIONS USABLE FOR THIS PURPOSE
CH1344376A CH602002A5 (en) 1975-10-29 1976-10-25
IT5189976A IT1123020B (en) 1975-10-29 1976-10-26 PROCEDURE FOR THE PRODUCTION OF FUNGICIDE COMPOSITIONS BASED ON PYRIMIDINMETHANOLS AND PRODUCT OBTAINED
PL1976193309A PL106521B1 (en) 1975-10-29 1976-10-27 FUNGICIDE
DD195482A DD126593A5 (en) 1975-10-29 1976-10-27
BR7607237A BR7607237A (en) 1975-10-29 1976-10-27 FUNGICIDAL COMPOSITES
DE19762648705 DE2648705A1 (en) 1975-10-29 1976-10-27 METHOD FOR PREPARING A FUNGICIDAL AGENT, FUNGICIDAL AGENT AND METHOD FOR TREATING FUNGAL INFECTIONS IN PLANTS
AT797476A AT353544B (en) 1975-10-29 1976-10-27 FIGHTING PHYTOPATHOGENIC MUSHROOMS
AR265256A AR215605A1 (en) 1975-10-29 1976-10-28 FUNGICIDE FORMULATIONS WITH SYNERGISTIC EFFECT
BE6045738A BE847771A (en) 1975-10-29 1976-10-28 PROCESS FOR TREATING FUNGAL INFECTIONS OF PLANTS AND FUNGICIDAL COMPOSITIONS USED FOR THIS PURPOSE,
BG7634549A BG27522A3 (en) 1975-10-29 1976-10-28 Fungicœde compositiow
CS766977A CS189039B2 (en) 1975-10-29 1976-10-28 Fundicide mixture
DK488776A DK152661C (en) 1975-10-29 1976-10-28 PROCEDURE FOR TREATMENT OR PREVENTION OF PLANT FUNGUS INFECTIONS AND FUNGICID PREPARATION FOR USING THE PROCEDURE
NO763677A NO763677L (en) 1975-10-29 1976-10-28
SU762415100A SU730269A3 (en) 1975-10-29 1976-10-29 Fungicide
SE7612063A SE430118B (en) 1975-10-29 1976-10-29 FUNGICID PREPARATION CONTAINING A PYRIMIDINE METHANOL AND 3A, 4,7,7A-TETRAHYDRO-N- (TRICHLOROMETHANESULPHENYL) PHTALIMIDE
JP51130386A JPS5254029A (en) 1975-10-29 1976-10-29 Mold killer
NLAANVRAGE7611998,A NL188139C (en) 1975-10-29 1976-10-29 A method for the preparation of a composition having a fungicidal action, a method for the preparation of a fungicidal composition, and a method for treating or preventing fungal infections in plants.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB44532/75A GB1561634A (en) 1975-10-29 1975-10-29 Fungicidal compositions

Publications (1)

Publication Number Publication Date
GB1561634A true GB1561634A (en) 1980-02-27

Family

ID=10433742

Family Applications (1)

Application Number Title Priority Date Filing Date
GB44532/75A Expired GB1561634A (en) 1975-10-29 1975-10-29 Fungicidal compositions

Country Status (25)

Country Link
JP (1) JPS5254029A (en)
AR (1) AR215605A1 (en)
AT (1) AT353544B (en)
AU (1) AU506064B2 (en)
BE (1) BE847771A (en)
BG (1) BG27522A3 (en)
BR (1) BR7607237A (en)
CA (1) CA1076024A (en)
CH (1) CH602002A5 (en)
CS (1) CS189039B2 (en)
DD (1) DD126593A5 (en)
DE (1) DE2648705A1 (en)
DK (1) DK152661C (en)
FR (1) FR2329200A1 (en)
GB (1) GB1561634A (en)
GR (1) GR61690B (en)
IE (1) IE43954B1 (en)
IL (1) IL50688A (en)
NL (1) NL188139C (en)
NO (1) NO763677L (en)
NZ (1) NZ182331A (en)
PL (1) PL106521B1 (en)
SE (1) SE430118B (en)
SU (1) SU730269A3 (en)
ZA (1) ZA766244B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1581527A (en) * 1976-08-18 1980-12-17 Lilly Industries Ltd Fungicidal formulations
GB1597363A (en) * 1977-09-07 1981-09-09 Lilly Industries Ltd Fungicidal combinations
CS217977B2 (en) * 1978-04-01 1983-02-25 Lilly Industries Ltd Fungicide means

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1569940A (en) * 1967-04-27 1969-06-06
US3887708A (en) * 1972-03-13 1975-06-03 Lilly Co Eli Alpha, alpha-disubstituted-5-pyrimidinemethanes used as fungicides

Also Published As

Publication number Publication date
AR215605A1 (en) 1979-10-31
JPS5254029A (en) 1977-05-02
DE2648705C2 (en) 1989-11-09
BE847771A (en) 1977-04-28
SE7612063L (en) 1977-04-30
DK152661C (en) 1988-08-22
AT353544B (en) 1979-11-26
NL188139C (en) 1992-04-16
DE2648705A1 (en) 1977-05-05
IE43954L (en) 1977-04-29
ZA766244B (en) 1978-05-30
IL50688A (en) 1980-06-30
DK152661B (en) 1988-04-11
JPS6117803B2 (en) 1986-05-09
SU730269A3 (en) 1980-04-25
BG27522A3 (en) 1979-11-12
PL106521B1 (en) 1979-12-31
CH602002A5 (en) 1978-07-14
GR61690B (en) 1978-12-09
NZ182331A (en) 1979-01-11
NL188139B (en) 1991-11-18
DD126593A5 (en) 1977-07-27
BR7607237A (en) 1977-09-13
CA1076024A (en) 1980-04-22
IL50688A0 (en) 1976-12-31
FR2329200A1 (en) 1977-05-27
SE430118B (en) 1983-10-24
CS189039B2 (en) 1979-03-30
IE43954B1 (en) 1981-07-15
NO763677L (en) 1977-05-02
AU1885876A (en) 1978-04-27
DK488776A (en) 1977-04-30
NL7611998A (en) 1977-05-03
ATA797476A (en) 1979-04-15
FR2329200B1 (en) 1980-05-09
AU506064B2 (en) 1979-12-13

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
704A Declaration that licence is not available as of right for an excepted use (par. 4a/1977)
PE20 Patent expired after termination of 20 years

Effective date: 19961027