DE2737313A1 - METHOD AND MEANS FOR PROTECTING WOOD AGAINST WOOD-COLLECTING FUNGI - Google Patents

Description

DR. A. VAN DERWERTH

DlPL-ING. (1934-1974)

PAT ENTAN WA LT E

DR. F-RANZ LEATHER

DIPL.-CHEM.

REINER F.MEYER

DIPL.-ING.

8000 MUNICH 80 LUCILE-GRAHN-STRASSE 22

TELEPHONE: (089) 472947 TELEX: 524624 LEATHER D TELEGR .: LEATHER PATENT

August 18, 1977 7740

A / S Cheminova Lemvig / Denmark

Process and means for protecting wood against wood-destroying fungi

The invention relates to a method and a means for protecting wood against wood-destroying fungi.

It is known that certain sulfenylimides show good fungicidal activity against phytopathogenic fungi. Among these compounds the following can be mentioned: Captan q

N-S-CCl-,

Folpet

N-S-CC1_ And

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Difolatan

CCl ₂ -CHCl ₂

It is also well known that these phytopathogenic fungicides have only very moderate effectiveness against wood-destroying ones Fungi such as Coniophora cerebella, Polyporus vaporarius and Merulius lacrymans.

It is also known, e.g. from DT-PS (patent application P 26 16 682.5) that the compound of the formula

IV CH, -S0 ₀ -NS-CC1_-CFC1 ₀

shows high activity against wood-destroying fungi, and this also applies to the compound of the formula V CH

N-SO ₂ -NS-CCl ₂ -CFCl ₂

and for the compounds described in U.S. Patent 3,796,802 of the formulas

VI

NS-CCl ₂ -CFCl ₂ and

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VII

NS-CCl ₀ -CFCl

It has now surprisingly been found that the strong reduction in the fungicidal effectiveness compared to wood-destroying Fungi that occurs when the fluorine atom in compound VII is replaced by a hydrogen atom Difolatan does not occur when the fluorine atom in compounds IV, V and VI is replaced by a hydrogen atom is replaced to form compounds I, II and III:

I. N-1,1,2,2-tetrachloroethylthio-N-phenylmethanesulfonamide

CH -SO ₂ -NS-CCI ₂ -CHC1

II. II, N-dimethyl-N '- (1,1,2,2-tetrachloroethylthio) -N ^f · phenyl-sulfonamide

CH CH

N-SO ₂ -NS-CCl ₂ -CHCl ₂

III. N-1,1,2,2-tetrachloroethylthiophthalimide

NS-CCl ₂ -CHCl ₂

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That is, it was found that the compounds I, II and III have excellent activity against wood-destroying Own fungi.

According to the invention is therefore a method for protecting Wood against attack by fungi, which is characterized in that the wood with an effective amount of a or more of the above compounds I, II and III is treated.

The invention also relates to an agent for treating wood in order to protect it against attack by fungi, one or more of the above compounds I, II and III in a carrier suitable for use on wood contains.

The treatment of wood with one or more of the compounds I, II and III can be done in any suitable way, preferably by one or the other of the methods known in the art, such as those in the technical literature are described. Detailed descriptions of suitable methods can be found, for example, in F.P. Kollmann and Wilfred A. Cote, Jr., "Principles of Wood Science and Technology," Volume 1, Chap. 5, pages 136-157 »Springer-Verlag, New York (1968) and F.P. Kollmaim, Wilfred A. Cote, Jr. and Alfred J. Stamm, "Principles of Wood Science and Technology", Volume 2, chap. 2, pages 107-111, Springer-Verlag, New York (1975). Suitable methods include, for example, surface treatment methods (such as by brushing or dipping), juice displacement methods (such as the Boucherie method), and egg holder impregnation methods (like the Rüping or Rütger method).

For all of these methods, the treatment agent preferably contains 0.1 to 10, particularly preferably 0.1 to 4 percent by weight of the active compound (on). Dis-

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The setting and in particular the concentration used is chosen in accordance with various factors, v / ie 2.B. the type of wood, the use for which the wood is intended, the degree of protection required and the Treatment method (e.g. brushing or impregnation under pressure), but professionals will have no difficulty select preferred compositions and treatment methods.

Suitable gowns according to the invention are manufactured, for example by incorporating one or more of compounds I, II and III in any of those normally used for wood preservatives liquids used, the liquid preferably being an organic liquid in which the active Compound is soluble in the desired concentration. Preferably a liquid hydrocarbon or a Hydrocarbon mixture used, particularly preferred a liquid aliphatic hydrocarbon or a mixture of such hydrocarbons, if desired with one lower proportion of liquid aromatic hydrocarbons or related compounds. White spirit or Kerosene or similar commercially available liquid hydrocarbon compounds are preferably used.

Daa means can, if desired, contain a component which serves to bind the active compound to wood. Suitable Binders for this purpose are known in the art and include, for example, alkyd resins, linseed oil, and others conventional film-forming materials. Appropriate concentrations of such binders depend on factors such as those above in connection with the concentration of the active ingredient and may, for example, be up to 10% by weight or even exceed it.

Particularly preferred agents according to the invention are liquid

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Means that contain about 4 percent by weight of one or more of the compounds I, II and III, etv / a 9 percent by weight of a conventional alkyd resin binder and about 87 weight percent white spirit.

Agents according to the invention can also be prepared by mixing one or more of the compounds I, II and III with one self-emulsifying oil, a wettable powder or dust. Such smocks can be found in the in the same way as plant protection products are used.

The agents according to the invention can be used to protect all types of wood which are susceptible to attack by wood-destroying Fungi are subject to, such as pine, fir, beech, e.g. in the form of posts, poles, boards, beams and everything other forms suitable for building purposes.

The compounds I, II and III can, for example, by reacting 1,1,2,2-tetrachloroethylthio-sulfenyl chloride can be made with the appropriate amide / imide. In particular, the connections can be made in the same way as in DT-OS 1800836, 1801203 and US-PS 3796802 for the corresponding fluorine-containing compounds IV, V and VI.

The agents according to the invention are more advantageous than the well-known and widely used wood protection compounds Pentachlorophenol, tributyltin oxide and dichlofluanide containing agents because the compounds I, II and III have a considerably greater activity against wood-destroying fungi. The connections I, II and III also have the advantage over the corresponding fluorine-containing compounds IV, V and VI that they are easier and cheaper to manufacture than the latter, especially because the compound 1,1,2,2-tetrachloroethylthiosulfenyl chloride is much more accessible than

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the compound 2-fluoro-1,1,2-trichloroethylthiosulfenyl chloride.

The compounds I, II and III also have compared to the known fungicidal compounds, pentachlorophenol, tributyltin oxide and dichlofluanid, and opposite the fluorine-containing compounds IV, V and VI have the advantage that they are generally considerably less toxic to Mammals are.

The following examples serve to illustrate the invention for a better understanding. All percentages are based on weight, unless otherwise stated.

example 1

Checking the effectiveness against wood-destroying fungi.

The effectiveness of compounds I, II and III and others of the above-mentioned compounds against wood-destroying fungi was investigated with regard to Coniophora cerebella. Pine wood samples measuring 7 × 1.6 × 0.2 cm were dried at 103 ° C. for 24 hours and then weighed.

A concentration series of 4, 2, 1, 0.5, 0.25 and 0.125 % of the compound to be investigated was prepared in the form of a solution in ethyl acetate with 9 % of an alkyd binder. The wood samples were impregnated by briefly immersing them in one of these solutions. The wet samples were weighed, the uptake being about 100 kg of solution per nr wood. Then the samples were dried for 2 days at room temperature. Three samples were impregnated with each concentration of the test compound and, after drying, packed in sterilizable plastic bags and sterilized with UV or gamma radiation.

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Glass bottles, which contained 500 ml of soil specially enriched with nutrients for the growth of Goniophora cerebella, were ^{sterilized by autoclaving at 120 °} C. for three hours and then cooled. The wood samples were placed in the bottles together with an untreated wood sample, the soil was inoculated with Coniophora cerebella, and incubation was carried out for 4 weeks at 22 ° C. and 70% relative humidity.

After incubation, the samples were carefully brushed, then dried and weighed. The weight loss of each sample was calculated as a percentage of the initial dry weight. Glass bottles in which the untreated wood sample had a weight loss of less than 20 % were discarded and the test was repeated.

The numerical values in the following table show the weight loss (as a percentage) as an average of 3 samples: *

Connection G
k % Concentration of
bond, % wt.
2% 1% 0.5% 18th > 20 active λ
/ Vol.
0.2594 0 fer-
.125% LD g / kg
orally,
mouse Schznp.
⁰ C Pentachlor
phenol 2 6th 0 4th > 20 > 20 0.1 Tributary tin
-oxide 0 0 1 12th > 20 > 20 0.2 Dichloflu-
anid 1 1 0 0 > 20 > -20 approx 1 * 0 I. 0 0 0 3 3 9 10 129 II 0 0 0 0 9 16 10 114 III 0 0 6th 12th 10 111-116

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AO

Captan k 8th > 20 > 20 > 20 > 20 approx 9 3 Folpet 6th 11 13th 18th > 20 > 20 10 Oifolatan 9 11 13th 18th > 20 > 20 approx 6th IV 0 0 0 0 0 6th approx 3 V 0 0 0 0 1 5 10 VI 0 0 0 0 2 6th - VII *
0 0 0 0 0 2 approx

Example 2

Investigation of general fungicidal effectiveness using the example of Pullularia pullulans and Aspergillus niger, which are also known to cause discoloration of painted surfaces and mold stains on textiles. .,

The compound to be examined was dissolved in ethyl acetate and 0.3 ml of the solution was uniformly spread over a piece Filter paper (Whatman No. 40) distributed. The paper surface

2
was 19.5 cm. After evaporation of the solvent, the paper was placed in an agar medium in a sterilized Petri dish and the medium was inoculated with an aqueous spore suspension of the appropriate fungus. After ten days of incubation at 29 ^° C. and 85 % relative humidity, the sample dish was examined. Tests that showed no sign of growth on or in a narrow zone around the filter paper were rated positive.

The following compounds were tested by this method, and the following table shows the slightest weight% concentration, which is necessary to obtain a positive test.

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link P. pullullans A. niger Pentachlorophenol
Tri butyl tin oxide
Oichlofluanxd 0.5
0.5
0.05 1
,1
0.05 I.
II
III 0.05
0.5
0.05 0.005
0.005
0.05 Captan
Folpet
Difolatan 0.1
0.02
0.005 1
0.1
0.005 IV
V
VI
VII 0.05
0.5
0.05
0.005 0.05
0.05
0.05
0.005

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Claims (2)

27 37 J 13 claims 1. A method of protecting wood against attack by fungi, comprising mixing it with an effective amount of an anti-fungi acting coat is treated, characterized in that one or more of the compounds N-1, 1,2,2-tetrachloroethylthio-IT-phenyl-me thanesulfonamide, N, N-diraethyl-N · - (1,1,2,2-tetrachloroethylthio) -N'-phenylsulfonamide and N-1,1,2,2-tetrachloroethylthiophthalimide is used will or will be. 2. Means for carrying out the method according to claim 1, characterized in that it has one or more of the compounds I, II and III and a carrier therefor. 809808/0957