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US3127311A - Fungicidal compositions - Google Patents

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US3127311A
US3127311A US3127311DA US3127311A US 3127311 A US3127311 A US 3127311A US 3127311D A US3127311D A US 3127311DA US 3127311 A US3127311 A US 3127311A
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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
    • A01N25/12—Powders or granules
    • A01N25/14—Powders or granules wettable
    • 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
    • A01N25/12—Powders or granules
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S424/00—Drug, bio-affecting and body treating compositions
    • Y10S424/09—Fish posts

Definitions

  • the present invention relates to and has as its objects new and useful compositions of organic fungicides, which contain in addition to known active fungicides certain special emulsifiers and other adjectives which render the inventive compositions highly active and especially stable.
  • the special ingredients contained in the inventively improved fungicidal compositions are fatty alcohol polyglycol ethers or fatty acid polyglycol esters, metal salts, special magnesium salts of fatty acids and lower aliphatic or aromatic poly-basic carbonic acids or hydroxy carbonic acids.
  • auxiliary agents in fungicidal compositions especially detergents, emulsifiers, hydrophobating agents, adhesives act on the time of action and rapidity of action in a negative way.
  • a theoretical example is the following: If an organic fungicide which acts by its decomposition products is brought into stable formulations, the particles are covered by water impenetrable layers and thereby the micro-particles are not able to be decomposed and there- The purpose of improving 3,127,311 Patented Mar. 31, 1964 by they become inert or less biologically active on the plant.
  • compositions of organic fungicides especially improved fungicidal spray compositions broadly may be obtained, if as auxiliary solvents fatty acid metal salts and fatty acid polyglycol esters or fatty alcohol polyglycol ethers or aryl-polyglycol ethers are used. Additionally a certain amount of a solid lower aliphatic dior polycarboxylic acid or an aromatic carboxylic acid should be present in the inventive fungicidal compositions.
  • Compositions of the above said type not only have a highly acute activity (rapid action), but they also render the organic fungicides a long lasting activity.
  • the compositions of the present invention also secure a good distribution on the plants. A redistribution on the sprayed plant organs by rain water also does not lead to such an amount as this is the case with other known fungicidal compositions.
  • the above mentioned polyglycol ethers may be an aryloxypolyglycol ether such as the reaction product of ethylene oxide or propylene oxide or mixtures thereof with phenol, the different cresols, and the like, hydroxy diphenyls (especially 0- or p-hydroxydiphenyl), with benzyl hydroxydiphenyl, and the like.
  • aryloxypolyglycol ether such as the reaction product of ethylene oxide or propylene oxide or mixtures thereof with phenol, the different cresols, and the like, hydroxy diphenyls (especially 0- or p-hydroxydiphenyl), with benzyl hydroxydiphenyl, and the like.
  • fatty alcohol polyglycol ethers such as the reaction products of C to C alcohols especially C to C alcohols with ethylene oxide or propylene oxide or mixture thereof.
  • Those reaction products are e.g. lauryl, stearyl, palmityl or oleyl polyglycol ethers.
  • polyglycol ethers there is to be understood a reaction product containing more than at least 2 glycol radicals in the molecule and usually not more than about glycol radicals. Most suitable are the commercially available polyglycol ethers containing average between about 8 to 20 glycol radicals.
  • the fatty acid glycerol esters as above mentioned should contain at least one unesterified OH-group. As examples there may be mentioned the lauric acid-glycerol-monoand -diesters, the palmitic acid-glycerol-monoand -diesters, the stearic acid-glyceroldiester (Emocithin) and the like.
  • Metal salts of fatty acids in the meaning of this invention are especially salts of C to C carbonic acids and should contain as a salt forming metal especially an alkaline earth metal (magnesium, calcium and the like), zinc, manganese, aluminium, iron, copper and the like.
  • Especially useful organic acids are lauric, stearic, palmitic, margaric, oleic, linoleic acid and the like.
  • Especially suitable solid lower aliphatic dior polybasic acids which are useful for the inventively used compositions are oxalic acid, maleic acid, succinic acid, adipic acid, malic acid, citric acid, and the like.
  • Aromatic acids are especially phthalic acid, salicylic acid, and the like.
  • Organic fungicides which may be formulated with the inventively used compositions are broadly the known compounds used in the field of plant protection as yet.
  • TMTD tetramethyl-thiuram disulfide, ferric dimethyl dithiocarbamate, manganese ethylene bis-dithiocarbamate, disodium ethylene bis-dithiocarbamate, zinc ethylene bis-dithiocarbamate, zinc dimethyl dithiocarbamate).
  • N-trichloromethyl mercaptoA-cyclohexene-l.Z-dicarboximide 2.3-dichloro-l.4-naphthoquinone
  • Z-heptadecyl glyoxalidine acetate dinitro-( l-methyl heptyl)-phenyl-crotonate.
  • a special advantage of the inventively used combinations is the fact that this combination does not decrease the biological activity, but protects the active compound against influences which ordinarily make the active compound less efiicient. It has even been found that the biological activity is greater than the activity of formulations of known constituents used as yet for practical purposes. A further advantage is the increased period of activity of the inventively used compositions.
  • the inventive compositions usually contain the active ingredient in an amount of 5 to 95%, the balance being inert materials and the inventively used additional compounds.
  • the polyglycol ether or polyglycol ester compound is present in an amount of 1 to 25% more specifically 2 to 8%.
  • the fatty acid salt in the inventively used compositions should be present in an amount of 1 to 15%, especially 2 to 10%.
  • the solid hydroxy carboxylic, dicarboxylic or polycarboxylic acid at last is present in an amount up to 10%, es ecially in an amount of 2 to 8%.
  • Inert materials used for the inventively described compositions are talc, chalk, kaoline, bentonite, kieselguhr and especially finely divided highly dispersable silicic acids in the form of their various commercially available brands.
  • N trichloro methyl-thic-(dimethyl-arninosulfonicacid-anilide) (a) 50.0% of N-trichloro-methyl-thio-(dimethylamino-sulfonic-acid-anilide) 4.0% of oleyl-polyglycol other 1.0% of magnesium stearate 8.0% of salicylic acid Rest finely divided silicic acid 50.0% of N-trichloro-methyl-thio-(dimethylamino sulfonic acid anilide) 10.0% of magnesium stearate 5.0% of decyl-polyglycol ether 8.0% of salicylic acid Rest finely divided silicic acid
  • An identical composition may be prepared from: N- tric-hloro-methyl mercapto 4-cyclo-hexene-1.Z-di-carboximide.
  • EXAMPLE 5 N-Tric/zlol'o-Methyl-Thio-(Dinlet/1ylamino-Sulfonic Acid Anilide) the same as described before. 5 Active Evaluation number ingredient l3 concc-ntra EXAMPL 1 tion, Un- Sprayed Tcti'amethyl-Thiul'am-D sulfide (TMTD) percent sprayed TEST ([0 Normal formulation (with emulsifier 0.025 7 31 only) 0.0125 2t 50 g t E 1 gg25 3; I; lngrc len va uaconcentration Imeunve combmanon g g numb Non-treated control 100 100 W l 0.025 25 e claim:
  • a ⁇ I a G V 1 0.0125 34 59 (0) up to 10% of a solid organic acid this acid being Inventive combmqfion 16 8-83 2 a member selected from the group consisting of a Q 010125 17 43 lower aliphatic dicarboxylic acid, a lower aliphatic Non'tmted comm 100 100 hydroxy-carboxylic acid and salicylic acid,
  • EXAMPLE 2 Fungicidal compositions containing an organic 35 fungicide in an amount from 5 to 95 together with r F L Zznc Ethylen BIS Dzthzoca bamate (ZINEB) (a) 2 to 10% OI fatty alcohol p yg y ethers, the fatty alcohol having 12 to 18 carbon atoms and g 'g Evaluatlon numb" being etherified with up to 50 glycol residues, and concentra- (b) 1 to 10% of fatty acid metal salts, the fatty acid g l gg' Sprawl 40 having 12 to 18 carbon atoms and the metal being a member selected from the group consisting of Normal formulation (commercially 0.05 5 15 9319mm, magneslum, Z1I1C and alumlruurn, and I available i 29 (c) up to 10% of a solid organic acid, this acid being 88 g 3 a member selected from the group

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  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

United States Patent M 3,127,311 FUNGECEDAL 0MPOSETIONS Gtto Telle and Ferdinand Grows, (Iolognetammheim,
Germany, assignors to Farbenfabriiren Bayer Aktiengesellseha'it, Leverlrusen, Germany, a corporation of Germany No Drawing. Filed lliar. 8, 19st, Ser. No. 13,453 @iaims priority, application Germany Mar. 10, 1959 d @laims. (62. 167-42) The present invention relates to and has as its objects new and useful compositions of organic fungicides, which contain in addition to known active fungicides certain special emulsifiers and other adjectives which render the inventive compositions highly active and especially stable. The special ingredients contained in the inventively improved fungicidal compositions are fatty alcohol polyglycol ethers or fatty acid polyglycol esters, metal salts, special magnesium salts of fatty acids and lower aliphatic or aromatic poly-basic carbonic acids or hydroxy carbonic acids.
The use of organic fungicides for combating of fungous diseases especially for culture purposes during the last years became of increased importance. Since the number of organic fungicides is limited there has been done a great amount of work in the formulating of these fungicides to achieve thereby some effects which were not obtained by compositions known as yet. One method to find new compositions was to create finely divided metal of microsized particles. This could be performed by using special powder mills. Another method to obtain compositions of organic fungicides with improved properties is the use of special detergents, emulsifiers, special inert materials and the like. known fungicides by a special formulation is not only to improve the activity, but also to broaden the time of activity and to give the compositions more rapid actions. It is known that as yet many organic fungicides regarding their immediate activity as well as their acute activity come within the range of the activity of inorganic metal compounds, especially coppcr fungicides. Sometimes they are even better than the latter. The disadvantage of organic fungicides regarding compatible copper sprays, however, is the fact that the time of activity is much shorter than the time of activity of copper compounds. This may be due to the reason that organic fungicides may be easier attacked by chemical influences than the extremely stable inorganic compounds.
It has been tried to improve the time of activity of organic fungicides by adding special compounds including detergents, emulsifiers, and the like. But as yet only very few formulations have been found which had an improved period of activity. Also some good compositions have been proven to be of special advantage only for one compound and the same composition could not be used advantageously regarding other organic fungicides. The cause for this fact might be due to the different mechanisms of action of the various organic fungicides. In the latter group there are as it is known two main classes of compounds. In one class the activity is due to the unchanged molecule, but other fungicides only act by their decomposition products, which are formed by hydrolysis, oxidation and other reactions on the plants.
Some auxiliary agents in fungicidal compositions especially detergents, emulsifiers, hydrophobating agents, adhesives act on the time of action and rapidity of action in a negative way. A theoretical example is the following: If an organic fungicide which acts by its decomposition products is brought into stable formulations, the particles are covered by water impenetrable layers and thereby the micro-particles are not able to be decomposed and there- The purpose of improving 3,127,311 Patented Mar. 31, 1964 by they become inert or less biologically active on the plant.
In accordance with the present invention it has now been found that improved compositions of organic fungicides, especially improved fungicidal spray compositions broadly may be obtained, if as auxiliary solvents fatty acid metal salts and fatty acid polyglycol esters or fatty alcohol polyglycol ethers or aryl-polyglycol ethers are used. Additionally a certain amount of a solid lower aliphatic dior polycarboxylic acid or an aromatic carboxylic acid should be present in the inventive fungicidal compositions. Compositions of the above said type not only have a highly acute activity (rapid action), but they also render the organic fungicides a long lasting activity. The compositions of the present invention also secure a good distribution on the plants. A redistribution on the sprayed plant organs by rain water also does not lead to such an amount as this is the case with other known fungicidal compositions.
The above mentioned polyglycol ethers may be an aryloxypolyglycol ether such as the reaction product of ethylene oxide or propylene oxide or mixtures thereof with phenol, the different cresols, and the like, hydroxy diphenyls (especially 0- or p-hydroxydiphenyl), with benzyl hydroxydiphenyl, and the like. Especially advantageous are fatty alcohol polyglycol ethers such as the reaction products of C to C alcohols especially C to C alcohols with ethylene oxide or propylene oxide or mixture thereof. Those reaction products are e.g. lauryl, stearyl, palmityl or oleyl polyglycol ethers. Under polyglycol ethers there is to be understood a reaction product containing more than at least 2 glycol radicals in the molecule and usually not more than about glycol radicals. Most suitable are the commercially available polyglycol ethers containing average between about 8 to 20 glycol radicals. The fatty acid glycerol esters as above mentioned should contain at least one unesterified OH-group. As examples there may be mentioned the lauric acid-glycerol-monoand -diesters, the palmitic acid-glycerol-monoand -diesters, the stearic acid-glyceroldiester (Emocithin) and the like. Metal salts of fatty acids in the meaning of this invention are especially salts of C to C carbonic acids and should contain as a salt forming metal especially an alkaline earth metal (magnesium, calcium and the like), zinc, manganese, aluminium, iron, copper and the like. Especially useful organic acids are lauric, stearic, palmitic, margaric, oleic, linoleic acid and the like.
Especially suitable solid lower aliphatic dior polybasic acids which are useful for the inventively used compositions are oxalic acid, maleic acid, succinic acid, adipic acid, malic acid, citric acid, and the like. Aromatic acids are especially phthalic acid, salicylic acid, and the like.
Organic fungicides which may be formulated with the inventively used compositions are broadly the known compounds used in the field of plant protection as yet. As examples there may be mentioned at first the well known thio-carbamates (TMTD=tetramethyl-thiuram disulfide, ferric dimethyl dithiocarbamate, manganese ethylene bis-dithiocarbamate, disodium ethylene bis-dithiocarbamate, zinc ethylene bis-dithiocarbamate, zinc dimethyl dithiocarbamate). Other examples are N-trichloromethyl mercaptoA-cyclohexene-l.Z-dicarboximide, 2.3-dichloro-l.4-naphthoquinone, Z-heptadecyl glyoxalidine acetate, dinitro-( l-methyl heptyl)-phenyl-crotonate.
A special advantage of the inventively used combinations is the fact that this combination does not decrease the biological activity, but protects the active compound against influences which ordinarily make the active compound less efiicient. It has even been found that the biological activity is greater than the activity of formulations of known constituents used as yet for practical purposes. A further advantage is the increased period of activity of the inventively used compositions.
The inventive compositions usually contain the active ingredient in an amount of 5 to 95%, the balance being inert materials and the inventively used additional compounds. Usually the polyglycol ether or polyglycol ester compound is present in an amount of 1 to 25% more specifically 2 to 8%. The fatty acid salt in the inventively used compositions should be present in an amount of 1 to 15%, especially 2 to 10%. The solid hydroxy carboxylic, dicarboxylic or polycarboxylic acid at last is present in an amount up to 10%, es ecially in an amount of 2 to 8%. Inert materials used for the inventively described compositions are talc, chalk, kaoline, bentonite, kieselguhr and especially finely divided highly dispersable silicic acids in the form of their various commercially available brands.
The following examples are given to illustrate this invention without, however, restricting it in any way:
(l) TetramethyLthiuram-disulfide (TMTD):
(a) 80.0% of tetramethyl-thiuram-disulfide 4.3% of oleyl-polyglycol ether 2.0% of magnesium stearate 6.0% of colloidal kaoline Rest finely divided silicic acid (b) 80.0% of tetramethyl-thiuram-disulfide 3.0% of oleyl-polyglycol other 1.0% of magnesium stearate 10.0% of adipic acid Rest silitine Z (finely divided silicic acid, commercially available) 60.0% of tetramethyl-thiuram-disulfide 8.0% of oleyl-polyglycolether 15.0% of magnesium stearate 3.0% of finely divided silicic acid, and Rest finely divided silicic acid (2) Zinc-ethylene-bis-dithiocarbamate (ZINEB):
(a) 80.0% of zinc-ethylene-bis-dithiocarbamate 4.5% of oleyl-polyglycol ether 2.0% of magnesium stearate Rest finely divided silicic acid (11) 60.0% of zinc-ethylene-bis-dithiocarbamate 4.0% of oleyl-polyglycol ether 2.0% of magnesium stearate Rest finely divided silicic acid (c) 80.0% of zinc-ethylene-bis-dithiocarbamate 3.0% of oleyl-polyglycol ether 1.0% of magnesium stearate 8.0% of salicylic acid Rest finely divided silicic acid (at) 60.0% of z nc-ethylene-bis-dithiocarbamate 15.0% of magnesium stearate 10.0% of oleyl-polyglycol ether Rest finely divided silicic acid (3) Zinc-dimethyl-dithiocarbamate (ZIRAM):
(a) 90.0% of zinc-dimethyl-dithiocarbamate 2.0% of magnesium stearate 4.0% of oleyl-polyglycol ether Rest finely divided silicic acid 1-chloro-2.4-dinitro-naphthaline (CDN): (a) 50.0% of 1-chloro-2.4-dinitro-naphthaline .0% of magnesium stearate 5.0% of oleyl-polyglycol ether 1.0% of naphthaline-sulfonate Rest finely divided silicic acid (b) 75.0% of 1-chloro-2.4-dinitr0-naphthaline 2.0% of magnesium stearate 4.0% of oleyl-polyglycol ether 2.0% of zinc oxide Rest finely divided silicic acid are completely destroyed by the fungus.
(5) N trichloro methyl-thic-(dimethyl-arninosulfonicacid-anilide) (a) 50.0% of N-trichloro-methyl-thio-(dimethylamino-sulfonic-acid-anilide) 4.0% of oleyl-polyglycol other 1.0% of magnesium stearate 8.0% of salicylic acid Rest finely divided silicic acid 50.0% of N-trichloro-methyl-thio-(dimethylamino sulfonic acid anilide) 10.0% of magnesium stearate 5.0% of decyl-polyglycol ether 8.0% of salicylic acid Rest finely divided silicic acid An identical composition may be prepared from: N- tric-hloro-methyl mercapto 4-cyclo-hexene-1.Z-di-carboximide.
In the following the superiority of the inventively used compositions regarding their acute activity and resistance to rain leaching is demonstrated with some organic protective fungicides on Phytophthora infes-tans (late blight, tomatoes).
The following method has been adopted: in the green house young tomato plants grown under standard conditions (soil, temperature, humidity and light) are used after the 4 to 5 first leaves are formed. The plants are then sprayed by normal means to running off with inventively used compositions in an aqueous dilution of the concentration shown in the tables below.
Thereafter they are placed for 24 hours in the green house to become dry (23 C.) (70 to relative humidity). Thereafter they are inoculated with zoospores of the fungus in bidistilled water. The plants then are placed for 5 days in a humidity chamber at relative humidity and at a temperature of 18 .to 20 'C. The plants treated as well as the inoculated plants during incubation are randomized in the humidity chamber. After the test is terminated the non-treated check plants The plants treated are evaluated by counting each leaf according to the destruction, whereby 6 values are used. According to this standard measure number the evaluation number may be obtained and compared with a non-treated control which is set 100. The evaluation numbers in the tables below thus give infestation in percent of the check.
It tested for resistance to rain leaching the plants when the spray is dried are sprayed by a finely divided measure spray of distilled water, corresponding to a quantity of 10 mm. rain during 10 minutes, on a turning table. The
as described above.
The plants thus treated and the plants non-sprayed (or rained) are artificially infested The other procedure is by the method given above.
EXAMPLE 5 N-Tric/zlol'o-Methyl-Thio-(Dinlet/1ylamino-Sulfonic Acid Anilide) the same as described before. 5 Active Evaluation number ingredient l3 concc-ntra EXAMPL 1 tion, Un- Sprayed Tcti'amethyl-Thiul'am-D sulfide (TMTD) percent sprayed TEST ([0 Normal formulation (with emulsifier 0.025 7 31 only) 0.0125 2t 50 g t E 1 gg25 3; I; lngrc len va uaconcentration Imeunve combmanon g g numb Non-treated control 100 100 W l 0.025 25 e claim:
a a l r Y 1 Normnlformul non (commoremymal able) 8-852 1. Funglcldal compositions containing an organic Inventive combination 010125 24 fungicide in an amount from 5 to 95% together With Non-treated control 100 (a) 2 to 10% of a member selected from the group consisting of phenyl hydroxy polyglycol ethers, fatty TEST acid polyglycol esters and fatty alcohol polyglycol etllers, the fatty alcohols and acids having 8 to Acme Evaluation number carbon atoms and being esterified Wlth up to 50 glycol residues, and c sprayed 25 (b) 1 to 16% of fatty acid metal salts, the fatty acid Percent sprayed having 8 to 25 carbon atoms and the metal being a member selected from the group consisting of call f f (cllmmercmuy 8-83 55 cium, magnesium, zinc and aluminium, and
a {I a G V 1 0.0125 34 59 (0) up to 10% of a solid organic acid, this acid being Inventive combmqfion 16 8-83 2 a member selected from the group consisting of a Q 010125 17 43 lower aliphatic dicarboxylic acid, a lower aliphatic Non'tmted comm 100 100 hydroxy-carboxylic acid and salicylic acid,
(d) the balance being inert filler. EXAMPLE 2 2. Fungicidal compositions containing an organic 35 fungicide in an amount from 5 to 95 together with r F L Zznc Ethylen BIS Dzthzoca bamate (ZINEB) (a) 2 to 10% OI fatty alcohol p yg y ethers, the fatty alcohol having 12 to 18 carbon atoms and g 'g Evaluatlon numb" being etherified with up to 50 glycol residues, and concentra- (b) 1 to 10% of fatty acid metal salts, the fatty acid g l gg' Sprawl 40 having 12 to 18 carbon atoms and the metal being a member selected from the group consisting of Normal formulation (commercially 0.05 5 15 9319mm, magneslum, Z1I1C and alumlruurn, and I available i 29 (c) up to 10% of a solid organic acid, this acid being 88 g 3 a member selected from the group consisting of a Inventive combination 2a 38%; g 5% lower aliphatic dicarboxylic acid, a lower aliphatic Nonmated control 100 m0 hydroxy-carboxyllc acld and salicylic acid,
(d) the balance being inert filler. 3. Fun 'cidal com osition containin an or anic EXAMPLE 3 g p g g Zinc-Dimcthyl-Dithiocarbamate (ZIRAM) fungicide in an amount from 5 to 95 together with (a) 2 to 10% of stearyl alcohol polyglycol ether being etherified with 5 to 25 glycol residues, and (b) 1 to 10% of magnesium stearate, and (0) up to 10% of a solid organic acid, this acid being a member selected from the group consisting of a lower aliphatic dicarboxylic acid, a lower aliphatic hydroxy-carboxylic acid and salicylic acid, (d) the balance being inert filler. 4. Fungicidal compositions containing an organic fungicide in an amount from 5 to 95 together with (a) 2 to 10% of palmityl alcohol polyglycol ether being etherified with 5 to 25 glycol residues, and calcium palmityl polyglycol ether, and (b) 1 to 10% of magnesium pahnitate, and (0) up to 10 of a solid organic acid, this acid being a member selected from the group consisting of a lower aliphatic dicarboxylic acid, a lower aliphatic hydroxy-carboxylic acid and salicylic acid, (d) the balance being inert filler.
References Cited in the file of this patent UNITED STATES PATENTS

Claims (1)

1. FUNGICIDAL COMPOSITIONS CONTAINING AN ORGANIC FUNGICIDE IN AN AMOUNT FROM 5 TO 95% TOGETHER WITH (A) 2 TO 10% OF A MEMBER SELECTED FROM THE GROUP CONSISTING OF PHENYL HYDROXY POLYGLYCOL E THERS, FATTY ACID POLYGLYCOL ESTERS AND FATTY ALCOHOL POLYGLYCOL ETHERS, THE FATTY ALCOHOLS AND ACIDS HAVING 8 TO 25 CARBON ATOMS AND BEING ESTERIFIED WITH UP TO 50 GLYCOL RESIDUES, AND (B) 1 TO 10% FATTY ACID METAL SALTS, THE FATTY ACID HAVING 8 TO 25 CARBON ATOMS AND THE METAL BEING A MEMBER SELECTED FROM THE GROUP CONSISTING OF CALCIUM, MAGNESIUM, ZINC AND ALUMINIUM, AND (C) UP TO 10% OF A SOLID ORGANIC ACID, THIS ACID BEING A MEMBER SELECTED FROM THE GROUP CONSISTING OF A LOWER ALIPHATIC DICARBOXYLIC ACID, A LOWER ALIPHATIC HYDROXY-CARBOXYLIC ACID AND SALICYCLIC ACID, (D) THE BALANCE BEING INERT FILLER.
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DEF27907A DE1139696B (en) 1959-03-10 1959-03-10 Fungicidal spray powder preparations based on organic active ingredients

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US4766153A (en) * 1986-04-30 1988-08-23 Sandoz Ltd. Alkyl polyoxyalkylene carboxylate esters and skin care compositions containing the same
WO2019077460A1 (en) * 2017-10-17 2019-04-25 Upl Ltd Novel agrochemical combinations

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US2731338A (en) * 1951-01-05 1956-01-17 Monsanto Chemicals Emulsifying and dispersing agents
US2913372A (en) * 1954-07-23 1959-11-17 Atlas Powder Co Compositions for dispersing powders in water
US2946721A (en) * 1954-12-17 1960-07-26 Gen Aniline & Film Corp Emulsification of water-insoluble organic solvents

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US2731338A (en) * 1951-01-05 1956-01-17 Monsanto Chemicals Emulsifying and dispersing agents
US2696453A (en) * 1952-05-27 1954-12-07 Herbert L Sanders Emulsifiers and toxicants containing the same
US2913372A (en) * 1954-07-23 1959-11-17 Atlas Powder Co Compositions for dispersing powders in water
US2946721A (en) * 1954-12-17 1960-07-26 Gen Aniline & Film Corp Emulsification of water-insoluble organic solvents

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4766153A (en) * 1986-04-30 1988-08-23 Sandoz Ltd. Alkyl polyoxyalkylene carboxylate esters and skin care compositions containing the same
WO2019077460A1 (en) * 2017-10-17 2019-04-25 Upl Ltd Novel agrochemical combinations
CN111683531A (en) * 2017-10-17 2020-09-18 Upl有限公司 New Agrochemical Portfolio
CN115530175A (en) * 2017-10-17 2022-12-30 Upl有限公司 Agrochemical combinations

Also Published As

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CH386766A (en) 1965-01-15
DE1139696B (en) 1962-11-15
NL249291A (en)
BE588509A (en)
GB905695A (en) 1962-09-12

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