NO813584L - THREE-PROTECTION REMEDY. - Google Patents

Description

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. agent, s<q>m...contains a triazolyl methyl ketal as active substance. From BRD official publication 25 51 560 it is known to use ~~l^TB^ryT)^å~lkyl~-i:H^ agriculture for ■ bek empelse. of. phytopathogenic fungi. The substances can also be used in the treatment of animals and people who are become ill due to the action of pathogenic microorganisms. It was now surprisingly found that triazolyl methyl ketals ~"with~f o.rm'ei.en — - •—'■ > _.. :.'

where R be ty r "fen. å IkyTFé siTTTiélJ~2~-*3 '~' K sthanstcmsx-, --e-r-me'get-^i-rk-= ningful against tree-discoloring fungi, decay fungi and wood-destroying fungi. Particularly effective are the compounds 1-M2-(2,4^dichlorophenyl)-4-ethyl-1,3-dioxolan-2-yl-methyl]-1H-1, 2, 4-triazole • (combustion deIse A ) and 1-[2-(2,4-dichlorophenyl)-4-propyl-1-1,3-dioxolan-2-yl-methyl]-1H-1,2,4-triazole (compound B).

The broad spectrum of activity of the active substances in the protection of wood could not be predicted in comparison to other known triazole derivatives used in agriculture, such as 1-(4-chlorophenoxy)-3,3-dimethyl-l- (1H-1,2,4-triazol-1-yl)-2-butanone (compound 1)' (BRD-of f. letter 22:oi 063) and bis-phenyl-(3-trifluoromethyl-phenyl)-1 -(1,2,4-triazolyl)-methane (compound 2) has an excellent fungicidal effect against phytopathogenic fungi, but is practically ineffective against wood-discoloring fungi and decay fungi.

The following wood and paint-staining fungi, decay fungi and wood-destroying fungi can, for example, be combated with the wood preservatives according to the invention: Pullularia (Auréobasidium pullulans), Sclerophoma p.ityophila, Ceratocystis spee, Paeci lpmycesvariptii, Hormiscium spee, Stemphyiium spee, Phoma violacea , • Cladosporium herbarum, Trichoderma viride, Chaetomium globosum, Humicola grisea, . . Merulius lacrimans, Coniophora puteana, Lentinus lepideus, Lenzites trabea, Trametes versicolor, Stereum hirsutum, Fornes annosus.

The new active substances can be used in preparations such as solutions, emulsions, pastes and oil dispersions. The preparations generally contain between 0.1<q>g and 90% by weight of active substance, preferably 0.25-50%; Amounts used are, depending on the nature of the desired effect, 0.5-8 g of active substance 2 per m wooden surface to be protected, or 50-40.00 g of active substance per m three. Paints/coating agents contain, for example, 0.5-2% by weight of active substance. By protection of. wooden materials, the active substances can be added as an emulsion, or by mixing (Untermischverfahren) added to the adhesive, for example in amounts of 2-6% by weight.

The application of the active substances takes place by application, s-spraying, showering, dipping or by pressure impregnation or diffusion methods.

To extend the spectrum of action or achieve special effects, the active substances can be combined with other active substances. Mixtures with the following compounds are considered particularly beneficial: Orgahotin compounds such as tributyltin oxide and tributyltin benzoate

methylene bisthiocyanate

alkyl-dimethyl-benzylammonium chloride cetyl-pyridinium chloride

chlorinated phenols, such as tetra- and pentachlorophenol tetrachloroisophthalic acid dinitrile.

2-Halobenzoic acid anilide •

N-cyclohexyl-N-methoxy-2,5-dimethyl-furan-3-carboxylic acid amide N,N-dimethyl-N'-phenyl-(N-fluoromethylthio)-sulfamide N-ferry 1-N ,N .' -dimethyl-N '-fluorodichloromethyl-thiosulfonyl-diamide benzimidazor-2-carbamic acid methyl ester

2-Thiocyanomethyl-thiobenzothiazole

copper naphthenate copper-8-oxyquinoline

alkali and metal salts of N'-hydroxy-N-cyclohexyl diazenium oxide

mercaptobenzthiazole N,N-Dimethyl-N'-(dichlorofluoromethylthio)-sulfamide p-chlorophenyl-3-propargyl-formal

3-iodo-2-propynyl-butyl-carbamate

Example 1.

When producing an oily wood protection agent with 1% active substance, one first dissolves 1 part (part by weight) of compound A under slight heating in 55 parts of an aromatic-rich petrol fraction. Then 10 parts of an alkyd resin, and test petrol is added at 100 parts at room temperature.

In a similar way, oily wood-protectors are produced. agents with 0.25-5% by weight of the active substances A and B.

For the production of water-repellent impregnation agents • so-called "water repellents" can be added to the oily wood protection agents. Suitable substances are, for example, zinc stearate, aluminum stearate, wax. Furthermore, it can for to achieve color effects, finely divided inorganic or organic pigments or oil-soluble dyes are incorporated into the preparations.

To protect the wood against fungal attack, 50-200 ml of the oily wood preservative specified in Example 1 is usually applied per m 2 treo.surface by applying, spraying or dipping.

Example 2

Filter paper discs with a diameter, on. 13 mm and a thickness of 1 mm is impregnated with 0.2 ml solutions in acetone containing

•respectively 200', 100, 50, 25 and 12.5 parts of active substance per parts per million solution (ppm). The slices are then placed on a 2% malt extract agar in Petri dishes, which have previously been inoculated separately with spores of the wood-discolouring fungi Pullularia pullulans and Trichoderma viride (green wood mould). The dishes were then set aside for 3 days at 2.2-24°C. After this .time

the fungi in the control dishes were very well developed.

The fungicidal effect of the active substances is assessed by

■ with the help of the fungus-free zones (inhibition zones) formed around the filter paper discs, as follows:

- . no zone of inhibition (no fungicidal action)

+ small inhibition zone 2 mm (small fungicidal effect)

++ medium, zone of inhibition 2-6 mm (good fungicidal effect) +++ large zone of inhibition 6 mm (very good fungicidal effect)

a) Pullularia pullulans

b). Trichoderma viride

Example 3

The active substances A, B as well as the comparators 1 and 2; is added, dissolved in acetone, in amounts of 40, 20 and 10 ppm to. a liquefied 5% malt extract agar. The agar is poured into Petri dishes, and after solidification the fungicide-containing curing agar plates are inoculated centrally with the fungus Chaetomium<g>lobosum, which causes rotting and black spots. The dishes are left for five days at 25°C, after which the development of the fungal colonies on the nutrient substrate is assessed in: comparison with the controls (without

addition of active substance):

0 no fungal growth (the fungus (Pilzmycel) killed).

1. = small fungal growth (1/3 of the agar surface overgrown)

3 = medium fungal growth (up to 2/3 of the agar surface overgrown) 5 = uninhibited fungal growth (entire agar surface, overgrown)

Example 4

They . active st-o-ffer^-A and B -are added, dissolved in acetone1, in amounts of 80, 40 and. 20 ppm to a 5% malt extract agar, as described in Example 3. The agar is poured ■ into petri dishes, and after solidification, the fungicide-containing nutrient agar plates are inoculated centrally with the mycelium of the wood-destroying fungi Coniophora puteana and Trametes versicolor. The dishes are left at 25°C for 5 days, after which the development of the fungal colonies on the nutrient substrate is assessed in comparison with the controls (without fungicide addition).

0 = no fungal growth (the fungus (Pilzmycel) killed)

1 = small fungal growth (1/3 of the agar surface covered)

3 = medium fungal growth (up to 2/3 of the agar surface covered)

5 = uninhibited fungal growth (entire agar surface overgrown) The test results show that the known fungicides triazole-. derivatives 1 and 2 only show a very small effect against fungi when it concerns the protection of wood, while the known fungicide triazole derivatives A and B surprisingly show a very good fungicidal effect against fungi when it comes to the protection of wood.

Example 5

10 parts by weight of compound B are dissolved in a mixture consisting of 90 parts by weight of xylene, 6 parts by weight of the addition product of 8-10 mol of oleic acid-N-monoethanolamide, .2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid and 2 parts by weight of the addition product of 40 mol of ethylene oxide and 1 mol castor oil.. This mixture is mixed with water to form an aqueous dispersion of the active substance.

Example 6

The fungicidal action against the . The wood-destroying fungi Coniophora puteana and Trametes versicolor were examined as follows: Pieces of pine wood with dimensions 50 x 25 x 15 mm were coated with oily preparations of wood preservative, which contained 1% by weight of the active substance B, in each case in quantities of 100 g of wood preservative per m three-over-surface. After four weeks of storage, the treated pieces of wood, together with similar untreated pieces of wood, were placed in glass dishes containing as test fungi respectively Coniophora puteana and Trametes versicolor on a nutrient agar. The dishes were then placed in a climate chamber at a temperature of 22°C and a rela -tive humidity of 70%. After three months, the pieces of wood were freed from adherent fungal mycelium and dried. Then the degree of wood destruction was determined.

Claims (5)

1; Wood preservative, characterized by that it contains a triazolylmethyl ketal with the formula where R means an alkyl residue with 2-3 carbon atoms. 2. Wood preservative, characterized in that it contains a solid or liquid carrier and a triazolylmethyl ketal with the formula where.R is an alkyl residue with 2-3 carbon atoms. 3. Method for the production of a wood preservative, characterized by mixing a solid or liquid carrier with a triazolyl methyl ketal with the formula. where R is an alkyl residue with 2-3 carbon atoms. 4. Procedure for protecting a <y> wood against discoloration and destruction by fungal attack, characterized by that one treats the wood with a triazolyl methyl ketal with the formula where R means an alkyl residue with 2-3 carbon atoms. 5. Wood preservative according to claim 1, characterized in that it contains 1-2-(2,4-di'chlorophenyl)-4-propyl-1,3dioxolan-2-yl-methyl-1H-1,2 , 4-triazole.