DE2341882A1 - N and metal salt contg. synergistic insecticide and fungicide - comprising methyl benzimidazole-2-carbamate and aluminium N-nitroso-N-cyclohexylhydroxyl-amine - Google Patents

N and metal salt contg. synergistic insecticide and fungicide - comprising methyl benzimidazole-2-carbamate and aluminium N-nitroso-N-cyclohexylhydroxyl-amine

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Publication number
DE2341882A1
DE2341882A1 DE19732341882 DE2341882A DE2341882A1 DE 2341882 A1 DE2341882 A1 DE 2341882A1 DE 19732341882 DE19732341882 DE 19732341882 DE 2341882 A DE2341882 A DE 2341882A DE 2341882 A1 DE2341882 A1 DE 2341882A1
Authority
DE
Germany
Prior art keywords
nitroso
carbamate
aluminium
amine
bcm
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.)
Granted
Application number
DE19732341882
Other languages
German (de)
Other versions
DE2341882C2 (en
Inventor
Ernst-Heinrich Dr Pommer
Wolfgang Dipl Chem Dr Reuther
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to DE19732341882 priority Critical patent/DE2341882A1/en
Priority to JP48113349A priority patent/JPS4993536A/ja
Priority to IT53066/73A priority patent/IT1053524B/en
Priority to US405807A priority patent/US3903288A/en
Priority to FR7336547A priority patent/FR2202649B1/fr
Priority to GB4772773A priority patent/GB1438154A/en
Publication of DE2341882A1 publication Critical patent/DE2341882A1/en
Application granted granted Critical
Publication of DE2341882C2 publication Critical patent/DE2341882C2/de
Granted legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
    • B27K3/34—Organic impregnating agents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
    • B27K3/34—Organic impregnating agents
    • B27K3/343—Heterocyclic compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
    • B27K3/34—Organic impregnating agents
    • B27K3/38—Aromatic compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
    • B27K3/34—Organic impregnating agents
    • B27K3/50—Mixtures of different organic impregnating agents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K5/00—Treating of wood not provided for in groups B27K1/00, B27K3/00
    • B27K5/02—Staining or dyeing wood; Bleaching wood

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Pesticidal compsns. contg. as active component a mixture of methyl benzimidazole-2-carbamate (BCM) or one of its alkali metal salts and aluminium N-nitroso-N-cyclohexylhydroxylamine (NCH). Synergistic fungicidal and insecticidal compsn. for prevention of attack on wood, for preservation of ind. prods. such as paints, leather, paper, adhesives etc. Pref. salts of BCM are the Na and K salts, esp the Na salt. Pref. ratios of BCM:Al NCH are 1:2 to 1:4.

Description

BASF Aktiengesellschaft 23Λ1882BASF Aktiengesellschaft 23Λ1882

Unser Zeichen: O. Z. 30 059 Sws/GOur reference: O. Z. 30 059 Sws / G

67OO Ludwigshafen, I6.8.I97367OO Ludwigshafen, August 16, 1973

SchädlingsbekämpfungsmittelPesticides

Die vorliegende Erfindung betrifft ein Schädlingsbekämpfungsmittel, das eine Mischung von Wirkstoffen enthält, und Verfahren zur Bekämpfung von Schädlingen mit dieser Mischung.The present invention relates to a pesticide, which contains a mixture of active ingredients, and methods for controlling pests with this mixture.

Es ist bekannt, Salze des N-Nitroso-N-cyclohexylhydroxylamins-(NCH) zum Schutz von Holz gegen den Angriff holzzerstörender Pilze, wie Coniophöra cerebella, Meruli.us lacrimans, Lentinus lepideus u.a., zu verwenden. Von den in Wasser praktisch unlöslichen Salzen hat sich das Aluminiumsalz des NCH bewährt; nachteilig ist jedoch, daß zum Schutz des Holzes verhältnismäßig hohe Anwendungskonzentrationen erforderlich sind. Ferner ist nachteilig, daß diese Verbindung gegen hoIzverfärbende Pilze, wie Pullularia pullulans und Sclerophoma pityophila,. in für die Bekämpfung holzzerstörender Pilze ausreichenden Anwendungskonzentrationen nicht' mehr wirksam ist.It is known that salts of N-nitroso-N-cyclohexylhydroxylamine- (NCH) to protect wood against attack by wood-destroying fungi, such as Coniophöra cerebella, Meruli.us lacrimans, Lentinus lepideus et al. Of the salts that are practically insoluble in water, the aluminum salt of the NCH has proven itself; disadvantageous is, however, that relatively high application concentrations are required to protect the wood. It is also disadvantageous that this compound against wood-discolouring fungi, such as Pullularia pullulans and Sclerophoma pityophila ,. in sufficient application concentrations for combating wood-destroying fungi is no longer effective.

Ferner ist es bekannt, daß sich mit dem 2-Benzimidazol-carbaminsäure-methylester (BCM) eine Vielzahl von Pilzen bekämpfen läßt, die vorwiegend den Pilzklassen der Ascomyceten und Fungi imperfecti angehören; gegen holzzerstörende Pilze aus der Klasse der Basidiomyceten ist diese Verbindung in üblichen Anwendungskonzentrat ionen unwirksam.It is also known that with the 2-benzimidazole-carbamic acid methyl ester (BCM) can be used to control a large number of fungi, mainly the Ascomycetes and Fungi imperfecti belong to; This compound is used in the usual concentrate against wood-destroying fungi from the Basidiomycete class ions ineffective.

Es wurde nun gefunden, daß eine Mischung aus dem 2-Benzimidazolcarbaminsäure-methylester und dem Aluminiumsalz des N-Nitroso-N-cyclohexylhydroxylamins als Schädlingsbekämpfungsmittel geeignetIt has now been found that a mixture of the methyl 2-benzimidazole carbamate and the aluminum salt of N-nitroso-N-cyclohexylhydroxylamine are suitable as pesticides

Schädlinge sind allgemein Pilze und Insekten, insbesondere solche Pilze und Insekten, die Holz, Holzanstriche oder AnstrichfarbenPests are generally fungi and insects, particularly those fungi and insects that affect wood, wood paints or paints

485/73 509811/1168 -2~ 485/73 509811/1168 - 2 ~

-2- O.Z. 30 059-2- O.Z. 30 059

schädigen.damage.

Die erfindungsgemäßen Schädlingsbekämpfungsmittel weisen eine über die Wirksamkeit der Einzelwirkstoffe hinausgehende fungizide Wirksamkeit auf, dih. es liegt eine Potenzierung der Wirksamkeiten vor. Das Mischungsverhältnis der Wirkstoffe kann in einem weiten Bereich schwanken. Beispielsweise wurde bei einem Gewichtsverhältnis Aluminiumsalz des NCH zu BCM wie 1 : 1 bis 10 : 1, vorzugsweise 2 : 1 bis 4 : 1, eine hervorragende Wirkung gegen Schädlinge erzielt.The pesticides according to the invention have a fungicidal effect that goes beyond the effectiveness of the individual active ingredients Effectiveness on, ie. there is a potentiation of the efficacies. The mixing ratio of the active ingredients can be in one vary over a wide range. For example, at a weight ratio of aluminum salt of the NCH to BCM such as 1: 1 to 10: 1, preferably 2: 1 to 4: 1, achieved an excellent effect against pests.

Ein Konservierungsmittel für Dispersibnsfarben kann bis zu 4$ (Gewichtsprozent) Aluminiumsalz des NCH und bis zu 1% BCM enthalten; eine optimale Mischung liegt bei 2$ Aluminiumsalz des NCH und 0,5$ BCM, bezogen auf das Gesamtgewicht der.Dispersionsfarbe, vor. Diese Mischung eignet sich in hervorragender Weise als Zusatz zu Dispersionsfarben für Anstriche in Feuehträumen zum Schutz gegen Pilzbewuchs.A paint preservative can contain up to $ 4 (weight percent) aluminum salt of the NCH and up to 1% BCM; an optimal mixture is 2 $ aluminum salt of the NCH and 0.5 $ BCM, based on the total weight of the emulsion paint. This mixture is ideally suited as an additive to emulsion paints for paints in fire rooms to protect against fungal growth.

Folgende anstrichverfärbende Pilze und Schimmelpilze lassen sich mit den erfindungsgemäßen Mitteln bekämpfen: Pullularia pullulans, Aspergillus niger, Bispora effusa, Stachybotrys atra, Trichoderma viride, Paecilomyces variotii, Cladosporium herbarum, Sclerophoma pityophila, Chaetomium globosum, Hormiscium spec, Stemphylium spec, Alternaria spec, Phoma violacea; außerdem sind sie gegen holzzerstörende Pilze, wie Merulius lacrimans, Coniophora cerebella, Lentinus lepideus, Poria vaporaria, Lenzites trabea, Paxillus panuoides, wirksam. Die erfindungsgemäßen Mittel lassen sich nicht nur als fungizid wirksame Bestandteile von Dispersionsfarben und als Konservierungsmittel für Farben verwenden, sondern sie eignen sich auch als Holzschutzmittel und zur Konservierung von technischen Produkten, wie Leder, Klebstoffen, Papier.The following paint discolouring fungi and molds can be combated with the agents according to the invention: Pullularia pullulans, Aspergillus niger, Bispora effusa, Stachybotrys atra, Trichoderma viride, Paecilomyces variotii, Cladosporium herbarum, Sclerophoma pityophila, Chaetomium globosum, Hormiscium spec, Stemphylium spec, Alternaria spec, Phoma violacea; they are also against wood-destroying fungi, such as Merulius lacrimans, Coniophora cerebella, Lentinus lepideus, Poria vaporaria, Lenzites trabea, Paxillus panuoides. Leave the agents according to the invention not only used as fungicidally active components of emulsion paints and as preservatives for paints, but they are also suitable as wood preservatives and for the preservation of technical products such as leather, adhesives, Paper.

Aus nachstehendem Beispiel geht die Wirksamkeit der beanspruchten Mischung hervor:The following example shows the effectiveness of the claimed mixture:

509811/1166 -3-509811/1166 -3-

-3- ο.ζ. 30 059-3- ο.ζ. 30 059

In eine Kunststoffdispersionsfarbe, die als Bindemittel ein Aerylsäureester-Copolymerisat enthält, werden zur Herstellung g9gen Schimmelpilzbewuchs widerstandsfähiger Anstrichfilme Wirkstoffgsmische aus dem Aluminiumsalz des NCH und dem BCM in den Verhältnissen 2 : 1, 3 : 1 und 4:1, bezogen auf das Gewicht der Wirkstoffe, in feinvermahlenar Form sorgfältig eingearbeitet. Die Konservierungsmittelzusätze zur Dispersionsfarbe betragen 1,5 bis h% (Gewichtsprozent). Zum Vergleich werden die Einzelwirkstoffe in Mengen von 0,5 bis 3$ in gleicher Weise der Dispersionsfarbe zugesetzt. Zur Ermittlung der Widerstandsfähigkeit der fungizid ausgerüsteten Anstrichfilme werden 50 x 50 mm große und 1 mm starke Kiefernholzbrettchen (Furniere) mit den Dispersionsfarben gleichmäßig bestrichen. Nach dem Antrocknen des Anstrichfilms werden die Brettchen in Petrischalen auf Biomalz-Nähragar gelegt und mit einer Pilzsporenaufschwemmung besprüht. Es werden Pilze verwendet, die auf Farbanstrichen vorkommen können: Pullularia pullulans, Sclerophoma pytiophila, Trichoderma viride, Penicillium funicolosutn, Alternaria tenus, Stemphylium spec, Cladosporium herbarum. Die Petrischalen werden bei Raumtemperatur aufgestellt und nach 2, 4 und β Wochen das Ausmaß der Pilzentwicklung auf den Anstrichfilmen beurteilt. Die in nachstehender Tabelle angeführten Versuchsergebnisse zeigen die überlegene fungizide Wirksamkeit der Wirkstoffmischungen im Vergleich mit den Einzelwirkstoffen.In a plastic emulsion paint containing an aerylic acid ester copolymer as a binder, active ingredient mixtures of the aluminum salt of the NCH and the BCM in the ratios 2: 1, 3: 1 and 4: 1, based on the weight of the active ingredients, are added to the production of mold growth resistant paint films , carefully incorporated in finely ground form. The preservative additives to the emulsion paint are 1.5 to h% (weight percent). For comparison, the individual active ingredients are added to the emulsion paint in amounts of $ 0.5 to $ 3 in the same way. To determine the resistance of the fungicidally treated paint films, 50 × 50 mm and 1 mm thick pinewood boards (veneers) are evenly coated with the emulsion paints. After the paint film has dried on, the tablets are placed in Petri dishes on organic malt nutrient agar and sprayed with a suspension of fungal spores. Fungi are used that can appear on paintwork: Pullularia pullulans, Sclerophoma pytiophila, Trichoderma viride, Penicillium funicolosutn, Alternaria tenus, Stemphylium spec, Cladosporium herbarum. The Petri dishes are set up at room temperature and the extent of fungus development on the paint films is assessed after 2, 4 and β weeks. The test results listed in the table below show the superior fungicidal effectiveness of the active ingredient mixtures in comparison with the individual active ingredients.

509811/1166 -4-509811/1166 -4-

O.Z. 30 059O.Z. 30 059

Dispersionsfarbe Zugesetzte Wirkstoffmenge in % Al-Salz des NCHEmulsion paint Amount of active ingredient added in % Al salt of the NCH

BCM Pilzentwicklung auf dem Anstrichfilm nach WochenBCM fungus development on the paint film after weeks

2 Wochen 4 Wochen 6 Wochen2 weeks 4 weeks 6 weeks

0,5
0,5
1
20.5
0.5
1
2 O O O OO O O O 1
0
0
01
0
0
0 1
1
0
01
1
0
0 1
1,5
2
3 1
1.5
2
3 O OOOO OOO 1
1
1
01
1
1
0 3
3
2
13
3
2
1 1
1,5
2
3 1
1.5
2
3 0,5
10.5
1 1
01
0 ro roro ro 3 x
3 x3 x
3 x (ohne Wirkstoff)(without active ingredient) 22 44th 55 Kontrollecontrol

χ Vorwiegend Alternaria und Trichodermaχ Predominantly Alternaria and Trichoderma

0 = Oberfläche frei von Pilzbewuchs, abgestuft bis0 = surface free of fungal growth, graduated up to

5 = Oberfläche total von Pilzen bewachsen5 = surface completely overgrown by fungi

509811/1166 -5- 509811/1166 -5-

Claims (2)

-5 · O.Z. 30 059 Patentansprüche-5 O.Z. 30 059 claims 1. Schädlingsbekämpfungsmitte!,enthaltend eine Mischung aus dem 2-Benzimidazol-carbaminsäure-methylester und dem Aluminiumsalz des N-Nitroso-N-cyclohexy!hydroxy!amins.1. Pest Control Agent !, containing a mixture of the 2-Benzimidazole-carbamic acid methyl ester and the aluminum salt of N-nitroso-N-cyclohexy! hydroxy! amine. 2. Verwendung einer Mischung gemäß Anspruch 1 als Schutzmittel für Holzanstriche oder Anstrichfarben.2. Use of a mixture according to claim 1 as a protective agent for wood paints or paints. BASF AktiengesellschaftBASF Aktiengesellschaft 509811/1166509811/1166
DE19732341882 1972-10-13 1973-08-18 N and metal salt contg. synergistic insecticide and fungicide - comprising methyl benzimidazole-2-carbamate and aluminium N-nitroso-N-cyclohexylhydroxyl-amine Granted DE2341882A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
DE19732341882 DE2341882A1 (en) 1973-08-18 1973-08-18 N and metal salt contg. synergistic insecticide and fungicide - comprising methyl benzimidazole-2-carbamate and aluminium N-nitroso-N-cyclohexylhydroxyl-amine
JP48113349A JPS4993536A (en) 1972-10-13 1973-10-11
IT53066/73A IT1053524B (en) 1972-10-13 1973-10-11 PESTICIDES AND THEIR USE TO PROTECT WOOD PAINTS FOR WOOD OR PAINTS
US405807A US3903288A (en) 1972-10-13 1973-10-12 Pesticide for the protection of wood comprising a mixture of methyl 2-benzimidazole-carbonate or a salt thereof and the aluminum salt of N-nitroso-N-cyclohexylhydroxylamine
FR7336547A FR2202649B1 (en) 1972-10-13 1973-10-12
GB4772773A GB1438154A (en) 1972-10-13 1973-10-12

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19732341882 DE2341882A1 (en) 1973-08-18 1973-08-18 N and metal salt contg. synergistic insecticide and fungicide - comprising methyl benzimidazole-2-carbamate and aluminium N-nitroso-N-cyclohexylhydroxyl-amine

Publications (2)

Publication Number Publication Date
DE2341882A1 true DE2341882A1 (en) 1975-03-13
DE2341882C2 DE2341882C2 (en) 1987-01-22

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DE19732341882 Granted DE2341882A1 (en) 1972-10-13 1973-08-18 N and metal salt contg. synergistic insecticide and fungicide - comprising methyl benzimidazole-2-carbamate and aluminium N-nitroso-N-cyclohexylhydroxyl-amine

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DE (1) DE2341882A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2359150A1 (en) * 1976-07-24 1978-02-17 Basf Ag TIN-TRIORGANIC DERIVATIVES OF HYDROXYDIAZENIUM OXIDES FOR USE AS FUNGICIDES
US5149365A (en) * 1988-07-21 1992-09-22 Schering Aktiengesellschaft Diorganotin compounds, and agents which have a bactericidal and fungicidal action and contain these compounds

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1024743B (en) * 1956-08-25 1958-02-20 Basf Ag Fungicides
FR2027479A1 (en) * 1968-12-31 1970-09-25 Basf Ag

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1024743B (en) * 1956-08-25 1958-02-20 Basf Ag Fungicides
FR2027479A1 (en) * 1968-12-31 1970-09-25 Basf Ag

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2359150A1 (en) * 1976-07-24 1978-02-17 Basf Ag TIN-TRIORGANIC DERIVATIVES OF HYDROXYDIAZENIUM OXIDES FOR USE AS FUNGICIDES
US5149365A (en) * 1988-07-21 1992-09-22 Schering Aktiengesellschaft Diorganotin compounds, and agents which have a bactericidal and fungicidal action and contain these compounds

Also Published As

Publication number Publication date
DE2341882C2 (en) 1987-01-22

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