DE3017123A1 - Copper fungicide aq. solns. - of copper ammine salt and ammonium salt of (meth)acrylic! acid (co)polymer - Google Patents

Copper fungicide aq. solns. - of copper ammine salt and ammonium salt of (meth)acrylic! acid (co)polymer

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Publication number
DE3017123A1
DE3017123A1 DE19803017123 DE3017123A DE3017123A1 DE 3017123 A1 DE3017123 A1 DE 3017123A1 DE 19803017123 DE19803017123 DE 19803017123 DE 3017123 A DE3017123 A DE 3017123A DE 3017123 A1 DE3017123 A1 DE 3017123A1
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Germany
Prior art keywords
copper
salt
polymer
parts
acrylic
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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.)
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Application number
DE19803017123
Other languages
German (de)
Inventor
Helmut 6719 Wattenheim Kraft
Gregor Dipl.-Chem. Dr. 6719 Wattenheim Ley
Ernst-Heinrich Dr. Pommer
Dietrich Dipl.-Chem. Dr. 6703 Limburgerhof Schlotterbeck
Heinz 6940 Weinheim Schumacher
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BASF SE
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BASF SE
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Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to DE19803017123 priority Critical patent/DE3017123A1/en
Priority to GR64628A priority patent/GR75196B/el
Priority to US06/252,800 priority patent/US4409358A/en
Priority to EP81102722A priority patent/EP0039788B1/en
Priority to DE8181102722T priority patent/DE3161008D1/en
Priority to AT81102722T priority patent/ATE4766T1/en
Priority to CA000375391A priority patent/CA1171426A/en
Priority to IL62645A priority patent/IL62645A/en
Priority to GB8112616A priority patent/GB2077740B/en
Priority to IE950/81A priority patent/IE51149B1/en
Priority to PT72950A priority patent/PT72950B/en
Priority to MA19338A priority patent/MA19132A1/en
Priority to ES501820A priority patent/ES501820A0/en
Priority to BR8102689A priority patent/BR8102689A/en
Priority to AU70015/81A priority patent/AU538632B2/en
Priority to HU811150A priority patent/HU184955B/en
Priority to JP6529581A priority patent/JPS56169694A/en
Priority to ZA00812901A priority patent/ZA812901B/en
Priority to DK194181A priority patent/DK160910C/en
Publication of DE3017123A1 publication Critical patent/DE3017123A1/en
Priority to US06/474,309 priority patent/US4528185A/en
Priority to KE3432A priority patent/KE3432A/en
Priority to MY469/86A priority patent/MY8600469A/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/13—Dicarboxylic acids
    • C07C57/145—Maleic acid
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • A01N37/04—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof polybasic
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • 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
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/16—Heavy metals; Compounds thereof
    • A01N59/20—Copper
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/126—Acids containing more than four carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
    • C07C55/02—Dicarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03—Monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03—Monocarboxylic acids
    • C07C57/04—Acrylic acid; Methacrylic acid

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

Abstract

New fungicides contain aqueous solutions of (a) a copper ammine salt and (b) the ammonium salt of a polymer consisting of 60-100% acrylic acid or methacrylic acid and 0-40% acrylic or methacrylic acid ester. The fungicides pref. contain 0.01-10% Cu, pref. in the form of the ammine complex. The polymer is in the form of its water-soluble ammonium salt and may be produced by usual polymerisation procedures. Fungicidal agents for use in plant protection (esp. against Phytophthora infestans on tomatoes and potatoes, Plasmopara viticola on vines, Pseudoperonospora humid on hops, Cercospora beticola on beet, Cercospora musae on bananas, Venturia inaequalis on apples, Exobasidium vexans on tea, and Hemileia vastatrix on coffee), in antifouling paints, and wherever undesirable growth by organisms is to be prevented. When the agents are applied, drying out of the solution leads to reaction between the polyanion of the polymer and the copper ammine complex to form a crosslinked water-insoluble metal poly-salt which shows good adhesion and retains its fungicidal effect for a prolonged period. The fungicidal activity is greater than that of known copper fungicides.

Description

Fungizidfungicide

In der GB-PS 1 394 990 sind bereits wasserlösliche Copolymere- angegeben,- die durch Polymerisation von 20 bis 60 Teilen Acrylsäure oder Methacrylsäure, 20 bis 70 Teilen Alkylacrylat oder -methacrylat und 5 bis 20 Teilen eines weichmachenden Monomeren entstehen sollen und in die Pflanzenschutzmittel eingelagert werden sollen. Die sauren Copolymere sollen dabei auch in Form ihrer Kupfersalze mit dem Pflanzenschutzmittel kombiniert werden können. Bei eigenen Versuchen, diese GB-PS nachzuarbeiten, wurden Jedoch keine brauchbaren Produkte erhalten.In GB-PS 1 394 990 water-soluble copolymers are already indicated, - by polymerizing 20 to 60 parts of acrylic acid or methacrylic acid, 20 up to 70 parts of alkyl acrylate or methacrylate and 5 to 20 parts of a plasticizing agent Monomers are to be created and in the pesticides are to be stored. The acidic copolymers should also be in the form of their copper salts with the crop protection agent can be combined. In my own attempts to rework this GB-PS, were However, no usable products received.

Es wurde nun eine einfachere fungizide Mischung mit guten Eigenschaften gefunden.It became a simpler fungicidal mixture with good properties found.

Gegenstand der Erfindung ist ein Fungizid enthaltend wäßrige Lösungen eines Kupferammin-Salzes und des Ammoniumsalzes eines Polymeren bestehend aus 60 bis 100 % Acrylsäure oder Methacrylsäure und 0 bis 40 % Acrylsäure- oder Methacrylsäureester.The invention relates to a fungicide containing aqueous solutions of a copper amine salt and the ammonium salt of a polymer consisting of 60 up to 100% acrylic acid or methacrylic acid and 0 to 40% acrylic acid or methacrylic acid ester.

Das erfindungsgemäße Fungizid enthält das Kupfer vorz.ugsweise in einer Menge von 0,01 bis 10-%. Das Kupfer liegt insbesonde-re als Amminkomplex [Cu(NH3)4] 2+ vor, wobei die Wahl des Anions beliebig ist. In der Regel wird man Jedoch den Komplex aus dem leicht zugänglichen Kupfer(II)--sulfat herstellen. Zur Bildung des Amminkomplexes können auch niedermolekulare flüchtige Amine verwendet werden.The fungicide according to the invention preferably contains the copper in an amount from 0.01 to 10%. The copper lies in particular as an ammine complex [Cu (NH3) 4] 2+, with any choice of anion. As a rule, however, you will Produce a complex from the easily accessible copper (II) sulphate. To form the Ammine complexes can also be used with low molecular weight volatile amines.

Die Polymeren werden in Form ihrer wasserlöslichen Ammoniumsalze verwendet. Sie können-nach den üblichen Verfahren der Substanz-, Lösungs-, Quellungs-, Emulsions-oder Suspensionspolymerisation erhalten werden.The polymers are used in the form of their water-soluble ammonium salts. They can - by the customary methods of substance, solution, swelling, emulsion or Suspension polymerization can be obtained.

So kann man beispielsweise die Monomeren unter Ausschluß von Sauerstoff in Isopropanol/Wasser 1:1 lösen, so daß eine 10 bis 50 %ige Lösung entsteht. Hierzu gibt man etwa 0,5 bis 5 % (bezogen auf die Menge der Monomeren) Polymerisationsinitiator, z.B. Azobisisobutyronitril, und erwärmt die Mischung 5 Stunden auf 8000. Die so erhaltenen Polymeren werden direkt oder nach Isolierung in Form ihrer Ammoniumsalze zur Herstellung des errindungsgemäßen Fungizids verwendet. Als Ammoniumsalze kommen auch hier die von Ammoniak und niedermolekularen flüchtigen Aminen in Frage.So you can, for example, the monomers in the absence of oxygen Dissolve in isopropanol / water 1: 1, so that a 10 to 50% solution is formed. For this are about 0.5 to 5% (based on the amount of monomers) polymerization initiator, e.g. azobisisobutyronitrile, and heats the mixture to 8000 for 5 hours The polymers obtained are directly or after isolation in the form of their ammonium salts used to produce the fungicide according to the invention. Come as ammonium salts also here the ammonia and low molecular weight volatile amines in question.

Trägt man das erfindungsgemäße Fungizid auf zu behandelnde Gegenstände oder Pflanzen auf, so entsteht beim Auftrocknen der Lösung durch Reaktion zwischen dem Poiyanion des Polymeren und dem Metallkomplex ein vernetztes wasserunlösliches Metallpolysalz, welches fest auf dem Gegenstand oder der Pflanze haftet und seine fungizide Wirkung über einen langen Zeitraum behält. Darüber hinaus besitzen die neuen Komplexe eine stärkere fungizide Wirkung als die bislang bekannten kupferhaltigen Fungizide. Die neuen Fungizide sind daher nicht nur als Antifouling-Anstriche einsetzbar, sondern auch überall dort, wo unerwünschter Bewuchs oder Befall durch Organismen auftritt. Beispiele hierfür sind die Hemmung von Algen-, Pilz-, Flechten- und Moosbefall von Bauteilen wie Natur- und-Kunststein, Pflaster und Fassaden, Putze, Anstriche, dem Wasser ausgesetzte Holzteile sowie Pflanzen. Insbesondere eignen sich die neuen Fungizide zur Bekämpfung von Phytophthora infestans an Tomaten und Kartoffeln, Plasmopara viticola an Reben, Pseudoperonospora humuli an Hopfen, Cercospora beticola an Rüben, Cercospora musae an Bananen, Venturia inaequalis an pfeln, Exobasidium vexans an Tee, Hemileia vastatrix an Kaffee.If the fungicide according to the invention is applied to objects to be treated or plants, it arises when the solution dries up through a reaction between the polyanion of the polymer and the metal complex a cross-linked water-insoluble Metal poly salt, which adheres firmly to the object or plant and its retains fungicidal effect over a long period of time. In addition, the new complexes have a stronger fungicidal effect than the previously known copper-containing ones Fungicides. The new fungicides can therefore not only be used as antifouling paints, but also wherever unwanted growth or infestation by organisms occurs. Examples of this are the inhibition of algae, fungus, lichen and moss infestation of components such as natural and artificial stone, paving and facades, plasters, paints, Wooden parts exposed to water and plants. The new ones are particularly suitable Fungicides to control Phytophthora infestans on tomatoes and potatoes, Plasmopara viticola on vines, Pseudoperonospora humuli on hops, Cercospora beticola on beets, Cercospora musae on bananas, Venturia inaequalis on apples, Exobasidium vexans on Tea, Hemileia vastatrix on coffee.

J 'Weiter besitzen die neuen Fungizide den Vorteil, daß sie aus rein wäßriger Lösung angewendet werden können, so daß keine Umweltbelastungen auftreten. J '' The new fungicides also have the advantage that they can be used from a purely aqueous solution, so that no environmental pollution appear.

In der Regei haften die neuen Über züge nach dem Versprühen gut auf den überzogenen Gegenständen bzw. Pflanzen. Falls Jedoch Schwierigkeiten hinsichtlich der Haftung auftreten, kann diese durch Zugabe eines Haftmittels ("sticker") verbessert werden. Als Haftmittel eignet sich beispielsweise eine Styrol/n-Butylacrylat-Dispersion, die unter der Bezeichnungronal 567 D erhältlich ist. As a rule, the new coatings adhere well after spraying the coated objects or plants. However, if there are difficulties regarding the adhesion occur, this can be improved by adding an adhesive ("sticker") will. A suitable adhesive is, for example, a styrene / n-butyl acrylate dispersion, which is available under the name ronal 567 D.

Die folgenden Beispiele sollen die Erfindung näher erläutern. Darin beziehen sich die Mengen- und Prozentangaben auf Gewichte.The following examples are intended to explain the invention in more detail. In this The quantities and percentages relate to weight.

Beispiel 1 Zu einer Lösung eines Lösungscopolymeren mit einem K-Wert von K = 46 aus 6,7 Teilen Methacrylat und 13,3 Teilen Acrylsäure in 96,25 Teilen Wasser und 3,75 Teilen konze-ntriertem Ammoniakwasser wurde unter Rühren eine Lösung von 30 Teilen CuS04 . 5 H20 in 75 Teilen Wasser und 45 Teilen konzentriertem Ammoniakwasser gegeben. Die erhaltene tiefblaue, klare Lösung ist lagerstabil und mit Wasser in Jedem Verhältnis mischbar. Der Kupfergehalt der Lösung beträgt 2,87 %.Example 1 To a solution of a solution copolymer with a K value of K = 46 from 6.7 parts of methacrylate and 13.3 parts of acrylic acid in 96.25 parts Water and 3.75 parts of concentrated ammonia water became a solution with stirring of 30 parts CuS04. 5 H20 in 75 parts of water and 45 parts of concentrated ammonia water given. The deep blue, clear solution obtained is stable in storage and in water Can be mixed in any ratio. The copper content of the solution is 2.87%.

Beispiel 2 Es wurde wie in Beispiel 1 verfahren, -Jedoch wurde ein Lösungscopolymerisat mit einem K-Wert von 42 aus 6,7 Teilen Ethylacrylat und 13,3 Teilen Acrylsäure verwendet.Example 2 The procedure was as in Example 1, but a Solution copolymer with a K value of 42 from 6.7 parts of ethyl acrylate and 13.3 Parts used acrylic acid.

Beispiel 3 Es wurde wie in Beispiel 1 verfahren, Jedoch wurde ein Lösungscopolymerisat vom K-Wert 41 aus 6,7 Teilen n-Butylacrylat und 13,3 Teilen Acrylsäure verwendet.Example 3 The procedure was as in Example 1, except that a Solution copolymer with a K value of 41 from 6.7 parts of n-butyl acrylate and 13.3 parts Acrylic acid used.

Beispiel 4 Zu einer 50 %igen Lösung eines Copolymeren des K-Werts K = 48 aus 25,1 Teilen Acrylsäure und12,4 Teilen n-Butylacrylat in Isopropanol/Wasser (1:1) wurden 37,5 Teile Wasser und 7,5 Teile konz. Ammoniak gegeben.Example 4 To a 50% solution of a copolymer of the K value K = 48 from 25.1 parts of acrylic acid and 12.4 parts of n-butyl acrylate in isopropanol / water (1: 1) 37.5 parts of water and 7.5 parts of conc. Given ammonia.

Dann wurden 60 Teile CuS04 . 5 H20 in 50 Teilen Wasser in der Hitze gelöst und zu dieser Lösung nach Abkühlen 120 Teile konz. Ammoniakwasser gegeben. Die erhaltenen Lösungen wurden vereinigt. Es entsteht eine tiefblaue, klare Lösung, die lagerstabil und mit Wasser in Jedem Verhältnis mischbar ist. Der Kupfergehalt der Lösung betrug 4,36 %.Then 60 parts of CuSO4. 5 H20 in 50 parts of water in the heat dissolved and 120 parts of conc. Given ammonia water. The resulting solutions were combined. The result is a deep blue, clear solution, which is stable in storage and miscible with water in any ratio. The copper content the solution was 4.36%.

Beispiel 5 Zu einer 25eigen Lösung eines Copolymeren des K-Werts K = 43 aus 12,5 Teilen Acrylsäure und 6,2 Teilen n-Butylacrylat in Isopropanol/Wasser (1:1) wurden 37,5 Teile Wasser und 3,75 Teile konz. Ammoniakwasser gegeben.Example 5 To an own solution of a copolymer with a K value of K = 43 from 12.5 parts of acrylic acid and 6.2 parts of n-butyl acrylate in isopropanol / water (1: 1) 37.5 parts of water and 3.75 parts of conc. Given ammonia water.

20 Teile CuS04 . 5 H20 wurden in 75 Teilen Wasser heiß gelöst. Die Lösung wurde abgekühlt und mit 35 Teilen konz.20 parts CuS04. 5 H20 were dissolved in 75 parts of hot water. the Solution was cooled and concentrated with 35 parts.

Ammoniakwasser versetzt. Die erhaltenen Lösungen wurden vereinigt. Der Kupfergehalt der Lösung betrug 2,11 %.Ammonia water added. The resulting solutions were combined. The copper content of the solution was 2.11%.

Beispiel 6 Zu der Lösung eines Lösungspolymerisats mit einem K-Wert von K = 20 aus 4,5 Teilen Acrylsäure in 33 Teilen Wasser und 10 Teilen konz. Ammoniakwasser wurde eine Lösung aus 30 Teilen CuS04 . 5 H20 in 60 Teilen konz. Ammoniak gegeben. Die erhaltene tiefblaue Lösung ist lagerstabil und mit Wasser in Jedem Verhältnis mischbar. Der Kupfergehalt der Lösung betrug-5,53 %.Example 6 To the solution of a solution polymer with a K value of K = 20 from 4.5 parts of acrylic acid in 33 parts of water and 10 Share conc. Ammonia water became a solution of 30 parts of CuSO4. 5 H20 in 60 Share conc. Given ammonia. The deep blue solution obtained is stable in storage and Miscible with water in any ratio. The copper content of the solution was -5.53 %.

Beispiel 7 Zu einer Lösung von 45 Teilen CuS04 . 5 H20 in 90 Teilen konz. Ammoniak wurde die Lösung eines Lösungspolymerisats mit einem K-Wert von etwa K = 20 aus 4,5 Teilen Acrylsäure in 49 Teilen Wasser und 10 Teilen konz. Ammoniakwasser zugetropft. Der Kupfergehalt der Lösung be-trug 5,78 %. Example 7 To a solution of 45 parts of CuSO4. 5 H20 in 90 parts conc. Ammonia was the solution of a solution polymer with a K value of about K = 20 from 4.5 parts of acrylic acid in 49 parts of water and 10 parts of conc. Ammonia water added dropwise. The copper content of the solution was 5.78%.

Beispiel A Fungizide Wirksamkeit gegen Phytophthora infestans an Tomaten.Example A Fungicidal activity against Phytophthora infestans on tomatoes.

Blätter von Tomatenpflanzen der Sorte "Professor Rudloff" werden mit wäßrigen Lösungen, die 0,6, Oj3, 0,15 und 0,07 % Kupfer (berechnet auf die Trockensubstanz) enthalten, besprüht. Nach dem Antrocknen des Spritzbelags werden die Blätter mit einer Zoosporenaurschwemmung des Pilzes Phytophthora infestans infiziert. Die Pflanzen werden dann in einer wasserdampfgesättigten Kammer bei Temperaturen zwischen 16 und 18°C aufgestellt. Nach 5 Tagen hat sich die Krankheit auf den unbehandelten, Jedoch infizierten Kontrollpflanzen so stark entwickelt, daß die fungizide Wirksamkeit der Substanzen beurteilt werden kann.Leaves of tomato plants of the "Professor Rudloff" variety are included aqueous solutions containing 0.6, 0.13, 0.15 and 0.07% copper (calculated on the dry matter) contain, sprayed. After the spray coating has dried on, the leaves become with infected by zoospore flooding of the fungus Phytophthora infestans. The plants are then placed in a steam-saturated chamber at temperatures between 16 and 18 ° C. After 5 days, the disease has spread to the untreated, However, infected control plants developed so strongly that the fungicidal activity developed of substances can be assessed.

Der Versuch ergab, daß Lösungen mit einem Kupfergehalt von etwa 0,1 % die Infektion sehr gut hemmen. Als besonders günstig haben sich die Fungizide der Beispiele 3 - -5 erwiesen. The experiment showed that solutions with a copper content of about 0.1 % inhibit the infection very well. Fungicides have proven to be particularly beneficial of Examples 3 - -5 proved.

Claims (3)

'Patentansprüche 1. Fungizid,enthaltend wäßrige Lösungen eines Kupferammin-Salzes und des Ammoniumsalzes eines Polymeren bestehend aus 60 bis 100 % Acrylsäure oder Methacrylsäure und 0 bis 40 % Acrylsäure- oder Methacrylsäureester.Claims 1. Fungicide containing aqueous solutions of a copper amine salt and the ammonium salt of a polymer consisting of 60 to 100% acrylic acid or Methacrylic acid and 0 to 40% acrylic or methacrylic acid esters. 2. Fungizid gemäß Anspruch 1, dadurch gekennzeichnet, daß der Gehalt an Kupfer 0,01 bis 10 % beträgt. 2. Fungicide according to claim 1, characterized in that the content of copper is 0.01 to 10%. 3. Fungizid gemäß Anspruch 1, dadurch gekennzeichnet, daß es als Acrylsäureester Butylaerylat enthält. 3. Fungicide according to claim 1, characterized in that it is used as Contains acrylic acid ester butyl erylate.
DE19803017123 1980-05-03 1980-05-03 Copper fungicide aq. solns. - of copper ammine salt and ammonium salt of (meth)acrylic! acid (co)polymer Withdrawn DE3017123A1 (en)

Priority Applications (22)

Application Number Priority Date Filing Date Title
DE19803017123 DE3017123A1 (en) 1980-05-03 1980-05-03 Copper fungicide aq. solns. - of copper ammine salt and ammonium salt of (meth)acrylic! acid (co)polymer
GR64628A GR75196B (en) 1980-05-03 1981-04-08
US06/252,800 US4409358A (en) 1980-05-03 1981-04-10 Copper complexes
EP81102722A EP0039788B1 (en) 1980-05-03 1981-04-10 Copper complexes, their preparation, their use in controlling plant pests and agents therefor
DE8181102722T DE3161008D1 (en) 1980-05-03 1981-04-10 Copper complexes, their preparation, their use in controlling plant pests and agents therefor
AT81102722T ATE4766T1 (en) 1980-05-03 1981-04-10 COPPER COMPLEXES, THEIR PRODUCTION, THEIR USE TO COMBAT PLANT PESTS AND MEANS FOR THEM.
CA000375391A CA1171426A (en) 1980-05-03 1981-04-14 Copper complexes, their preparation, their use in controlling plant pests, and agents for such control
IL62645A IL62645A (en) 1980-05-03 1981-04-14 Copper complexes,their preparation and their use in controlling plant pests
GB8112616A GB2077740B (en) 1980-05-03 1981-04-23 Copper complexes and their use in controlling plant pests
MA19338A MA19132A1 (en) 1980-05-03 1981-04-29 COPPER COMPLEXES, THEIR PREPARATION, THEIR USE FOR THE CONTROL OF PLANT PESTS AND PEST CONTROL PRODUCTS THAT CONTAIN THEM.
PT72950A PT72950B (en) 1980-05-03 1981-04-29 Process for the preparation of complex copper salts having phytosanitary effect and phytosanitary compositions containing them
IE950/81A IE51149B1 (en) 1980-05-03 1981-04-29 Copper complexes,their preparation,their use in controlling plant pests,and agents for such control
ES501820A ES501820A0 (en) 1980-05-03 1981-04-30 PROCEDURE FOR OBTAINING COPPER AMINOACATES
BR8102689A BR8102689A (en) 1980-05-03 1981-04-30 PROCESS OF PREPARATION OF COPPER COMPLEXES, APPLICABLE TO COMBAT PHYTOPATHOGENIC ORGANISMS AND THEIR COMPOSITION
AU70015/81A AU538632B2 (en) 1980-05-03 1981-04-30 Copper complexes and their use in controlling plant pests
HU811150A HU184955B (en) 1980-05-03 1981-04-30 Pesticide compositions containing complex copper compounds
JP6529581A JPS56169694A (en) 1980-05-03 1981-05-01 Copper ammine salt, its manufacture, plant protection agent containing it and expulsion of plant disease and vermin
ZA00812901A ZA812901B (en) 1980-05-03 1981-05-01 Copper complexes,ther preparation,their use in controlling plant pests,and agents for such control
DK194181A DK160910C (en) 1980-05-03 1981-05-01 PLANT COMPATIBLE COPPERAMINE SALT OF A POLYCARBOXYLIC ACID WITH FUNGICIDE AND BACTERICIDE EFFECTS AND PROCEDURES FOR COMBATING PLANT INFANTRY OR BACTERIA
US06/474,309 US4528185A (en) 1980-05-03 1983-03-11 Copper complexes, their preparation, their use in controlling plant pests, and agents for such control
KE3432A KE3432A (en) 1980-05-03 1984-07-26 Copper complexes their preparation their use in controlling plant pests and agents for such control
MY469/86A MY8600469A (en) 1980-05-03 1986-12-30 Copper complexes their preparation their use in controlling plant pests and agents for such control

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19803017123 DE3017123A1 (en) 1980-05-03 1980-05-03 Copper fungicide aq. solns. - of copper ammine salt and ammonium salt of (meth)acrylic! acid (co)polymer

Publications (1)

Publication Number Publication Date
DE3017123A1 true DE3017123A1 (en) 1981-11-05

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DE19803017123 Withdrawn DE3017123A1 (en) 1980-05-03 1980-05-03 Copper fungicide aq. solns. - of copper ammine salt and ammonium salt of (meth)acrylic! acid (co)polymer

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Country Link
JP (1) JPS56169694A (en)
DE (1) DE3017123A1 (en)
HU (1) HU184955B (en)
ZA (1) ZA812901B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
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WO1982003817A1 (en) * 1981-05-08 1982-11-11 Sundman Carl Erik Wood preservative compositions
DE3520313A1 (en) * 1984-06-20 1986-01-09 Kemira Oy, Helsinki WOOD PRESERVATIVES
DE102006008843A1 (en) * 2006-02-25 2007-08-30 Spiess-Urania Chemicals Gmbh Method for treatment of wood using copper-amine complex containing wood preventives, involves extracting active amine from wood impregnated with wood preservative
WO2022118255A1 (en) * 2020-12-02 2022-06-09 Adama Makhteshim Ltd. Copper-based fungicide composition

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JP2530201B2 (en) * 1988-03-02 1996-09-04 北興化学工業株式会社 Adhesion improver and pesticide powder with good adhesion
ZA931681B (en) * 1992-04-03 1993-12-07 Griffin Corp Copper complex bactericide/fungicide and method of making same
DE10351004A1 (en) * 2003-10-30 2005-05-25 Basf Ag Aqueous nanodispersion-forming formulations of active agents, especially plant protectants such as fungicides, comprise random copolymer of unsaturated sulfonic acid(s)
EP1961306A4 (en) * 2005-12-16 2012-03-28 Riken Bactericide for agricultural and horticultural use containing inorganic copper compound as active ingredient
AU2011293555A1 (en) * 2010-08-27 2013-02-07 Gowan Comercio Internacional E Servicos Limitada Plant treatment compositions and methods for their use
US9474282B2 (en) * 2013-12-13 2016-10-25 Tony John Hall Acid-solubilized copper-ammonium complexes and copper-zinc-ammonium complexes, compositions, preparations, methods, and uses
CN108024530B (en) * 2015-09-30 2022-09-20 陶氏环球技术有限责任公司 Process for preparing antimicrobial compositions
JP6757181B2 (en) * 2016-05-31 2020-09-16 株式会社日本触媒 Antibacterial agent

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JPS54117024A (en) * 1978-03-01 1979-09-11 Bp Chem Int Ltd Copper ammonium complex composition * production thereof and protection of base substance
NO810830L (en) * 1980-03-22 1981-09-23 Bp Chem Int Ltd METALAMINE CARBOXYLATES AND THEIR USE AS PRESERVATIVES

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1982003817A1 (en) * 1981-05-08 1982-11-11 Sundman Carl Erik Wood preservative compositions
DE3520313A1 (en) * 1984-06-20 1986-01-09 Kemira Oy, Helsinki WOOD PRESERVATIVES
DE102006008843A1 (en) * 2006-02-25 2007-08-30 Spiess-Urania Chemicals Gmbh Method for treatment of wood using copper-amine complex containing wood preventives, involves extracting active amine from wood impregnated with wood preservative
WO2022118255A1 (en) * 2020-12-02 2022-06-09 Adama Makhteshim Ltd. Copper-based fungicide composition

Also Published As

Publication number Publication date
JPH0413321B2 (en) 1992-03-09
ZA812901B (en) 1982-05-26
JPS56169694A (en) 1981-12-26
HU184955B (en) 1984-11-28

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