CA1272853A

CA1272853A - Wood preservative

Info

Publication number: CA1272853A
Application number: CA000502836A
Authority: CA
Inventors: Wolfgang Reuther; Horst Sommer; Dietrich Mangold; Ernst-Heinrich Pommer; Hans-Volker Borck
Original assignee: BASF SE
Current assignee: BASF SE
Priority date: 1985-03-02
Filing date: 1986-02-27
Publication date: 1990-08-21
Anticipated expiration: 2007-08-21
Also published as: JPS61202801A; NO860755L; EP0193890B1; EP0193890A1; NO167013C; FI860750L; NO167013B; DE3507420A1; DE3660709D1; FI860750A7; FI860750A0; ATE37157T1; JPH07115327B2

Abstract

ABSTRACT OF THE DISCLOSURE:

Disclosed is a method of controlling wood-damaging fungi, using N-tridecyl-2,6-dimethylmorpholine active ingre-dient for such a control.

Description

Wood preservative ~ he present invention relates to a method of con-t~ollin~ wood damaging fungi, using N-tridecyl-2,6-dimethyl-morpholine as active ingredient for such a control.

S DE 1 164 152 d;scloses that substituted morpholine ~erivat;ves can be used in agr;culture for controlling phytopathogenic fungi. These active ;ngredients, in par-t;cular N-tr;decyl-2,6-dimethylmorpholine (tridemorph~, have been used principally ;n cereals for controlling powdery m;ldew fung; wh;ch belong to the class cons;sting o~ the Ascomycetes fung;. Cereal rust fungi, such as barley brown rust or wheat brown rust, which are class;-fied among the Basidiomycetes fungi, are not controlled by tr;demorph.
tS It has also been d;sclosed that N-tr;decyl-2,6-trans-d;methyLmorphol;ne can be used for controll;ng wood-destroying fungi, such as Coniophora and Polyst;ctus ~European Patent 129r211).
We have found, surpr;s;ngly, that N-tr;decyl-2,6-?o d;methylmorpholine ;s substantially more effective than N-tr;decyl-2,6-trans-d;methylmorphol;ne against those fung; which infest and destroy wood, in part;cular timber which is no longer alive. The following wood-destroy;ng fung; t~as;diomycetes) can be controlled with, for ex-ample, the novel wood preservative: Merul;us lacr;mans,Con;ophora puteana, Lentinus lepideus, Lenzites trabea, Polystictus versicolor and Por;a vaporaria.
Examples of t;mber wh;ch ;s no longer al;ve (dead) are sawn wood, structural timber, woodworking materials, eg. ch;pboards, and woodshavings. For the purposes of the present invent;on, N-tr;decyl-Z,6-d;methylmorpholine ;s both the act;ve ingredien~ itself and its salts with ;n-organ;c or organic acids, for example salts w;th hydro-~luoric ac;d, hydrochloric acid, hydrobrom;c acid, sulfur;c acid, acetic ac;d or propionic ac;d~
The act;ve ;ngredient can be used in formulat;ons such as solut;ons, emulsions, pastes, coating agents .
. . . - :

~1 ~7;~35~

- 2 - o.Z. 0050/375~9 ~eg. paints and dressings) and oil dispersions. The for-mulations generally contain from 0.1 to 90, preferably from 0.25 to 50, % by weight of active ingredient. The amounts used depend on the type of effect desired and are S from 0.5 to 8 g of active ingredient per m2 of wood surface to be protected, or from 50 to 4000 g of active ingredient per m of wood. Coating agents contain, for example, from 0.5 to 4 % by weight of active ingredient. To pro-tect woodworking materials, the active ingredients can be added as an emulsion to the binder, for example in amounts of from 2 to 6 % by weight.
The active ingred;ent is applied in a conventional manner, for example by painting, spraying, atomizing or dipp;ng or by a pressure impregnation or diffusion method.
The Examples which follow illustrate the inven-tion. Percentages are by weight.

~ood preservative primer, colorless 2.00 % of tridemorph, 0.10 % of permethrin, 0.50 % of dichlofluanid, 6.00 % of linseed oil and 91.40 % of mineral spirit (bp. 180-Z20C).

Transparent wood preservative, colored 1 00 % of tridemorph, 0.10 % of permethrin, 0.50 % of dichlofluanid, 15.00 % of alkyd resin,

3.00 % of butylglycol, 3.00 % of iron oxide pigment, 0.20 % of siccative and 77.20 % of mineral spirit ~bp. 180-Z20C).

Yacuum impregnation oil 2.00 % of tridemorph, 0.50 % of dichlofluanid, ~L~7~3 - 3 - O.Z. 0050/37599 3.00 % of dibutyL phthalate and 94.50 ~ of mineral spirit (bp. 180-220C).

Wood preservative primer, water-dilutable 2.00 % of tridemorph~
3.00 % of dimethylalkylbenzylammonium chloride, 1.00 % of an adduct of ethylene oxide (E0) with nonyl-phenol (about 10 moles of E0 per mole of phenol), 3.00 % of acetic acid, 5.00 % of propylene glycol and 86.00 % of water.
To increase the action spectrum or to achieve special effects, the active ingredients car be combined with other active ingredients. Mixtures with the following compounds are regarded as particularly advantageous:
organotin compounds, such as tributyl-tin oxide and tri-butyl-tin benzoate, methylene bisthiocyanate, dimethylalkylamine salts, dimethyldialkylammonium chlorides, dimethylalkylbenzylammonium chlorides, trimethylalkylammonium chlorides, dimethylbipyridinium chloride, cetylpyridinium chloride, chlorophenols, such as tetra- and pentachlorophenol, tetrachloroisophthalodinitrile, 2-halobenzanilide, N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide, N,N-dimethyl-N'-phenyl-(N-fluoromethylthio)-sulfamide, N,N-dimethyl-N'-tolyl-(N-fluoromethylthio)-sulfamide, methyl benzimidazole-2-carbamate, 2-thiocyanomethylthiobenzothiazole, copper naphthenate, copper 8-hydroxyquinoline, alkali metal and metal salts of N'-hydroxy-N-cyclohexyl-diazenium oxide, 1-(1',2',4'-triazol-1'-yl)-~1-(4'-chlorophenoxy)]-3,3-, ~7;~8~3

- 4 - o.Z. 0050/3759 dimethylbutan-2-one, 1-t1',2',4'-triazol-1'-yl)-~1~(4'-chlorophenoxy)]-3,3-dimethylbutan-2-ol, ~-C3-~p-tert.-butylphenyl)-2-methylpropyl]-cis-2,6-S dimethylmorpholine,hexachlorocyclohexane, 0,0-d;ethyl 0-(~-cyanobenzylideneamino) thiophosphate, 0,0-diethyl 0-(3,5,6-trichloropyrid-Z-yl) thionophosphate, 0,0-diethyldithiophosphorylmethyl-6-chlorobenzoxazolone, 2-isopropoxyphenyl N-methylcarbamate, naphth-1-yl N-methylcarbamate, norbornene dimethanolhexachlorocyclosulfite, 1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)-urea, 1-C2-t2,4-dichlorophenyl)-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole~l-C2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-lH-1,2,4-triazole, 1-C2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-yl-ethyl]-lH-1,2,4-triazole, and synthetic pyrethroids, such as 3-phenoxybenzyl (+)-3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropane-1-carboxylate, ~ -cyano-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-di-methylcyclopropane-1 carboxylate, ~ -cyano-m-phenoxybenzyl 3-(2,2-dibromovinyl)-2,2-dimethyl-1R,3R-cyclopropanecarboxylate and ~-cyano-3-phenoxybenzylisopropyl 2,4-chlorophenylacetate.

To prepare an oily wood preservative containing 1 % of active ingredient, 1 part by weight of the active ingredient is first dissolved in 55 parts of a gasoline fraction having a high aromatics content, with gentle heating. 10 parts of an alkyd resin are then added, and the mixture is made up to 100 parts with mineral spirit at room temperature.
To prepare water-repellent impregnating paints~
water repellents are added to the oily wood preservatives.

.
.

_ 5 _ o z 0050/37599 Examples of suitable substances are zinc stearate, aluminum stearate and waxn Furthermore, in order to achieve color effects, finely divided inorganic or organic pigments or oil-soluble S dyes can be incorporated in the formulations.
To protect the wood from fungal infestation, from 50 to 200 ml of the oily wood preservatives mentioned in Example 5 are applied per m2 of wood surface, by brushing on, spray;ng or dipping.
Use E_am~le 1 Tridemorph dissolved in acetone is added, in amounts varying stepwise from 100 ppm to 3 ppm, to a 5 %
strength malt extract agar. The agar is poured ;nto Petr; d;shes; after the agar has sol;dified, the fung;-`lS c;de-containing nutrient agar plates are ;noculated separately w;th the mycelium of the wood-destroying fungi Merulius lacrimans, Coniophora puteana, Lenzites trabea~
pOlyctictus versicolor and Poria vaporaria. When the dishes have been incubated for five days at 25C, the development of the fungal colonies on the nutrient substrate is assessed in comparison with N-tridecyl-2,6-trans-dimethylmorphol;ne (A) and the con-trol (w;thout the add;tion of fungicide).
0 = no fungal yrowth (mycel;um destroyed) 1 = sl;ght fungal growth (up to 1/3 of the agar surface covered w;th growth) 2 = moderate fungal growth (up to 2/3 of the agar surface covered with growth)

5 = un;nh;b;ted fungal growth (total agar surface covered w;th growth) Test fungus ... ppm of tr;demorph added to the nutrient agar lOo so 25 _2 6 3 0 (control) Merulius lacrimans O O O 0 1 1 5 Coniophora puteana 1 1 1 1 3 3 s Len~ites trabea 0 0 0 0 0 1 5 Polystictus versicolor ' O O O 1 1 3 5 Poria vaporaria O O O O O 0 5 .

7~8~3

- 6 - O.Z. 0050/37599 Test fungus ... ppm of active ingredient A added to the nutrient agar 1ao 50 2s 12 6 3 0 (control) Merulius lacrimans O o 0 5 5 5 5 Coniophora puteana 3 3 3 S S 5 S
Polystictus versicolor o 1 2 ~ 5 s 5 Use Example 2 The following limiting values, ie. the amount of the active ingredient tridemorph required for protecting 1 m3 of wood, were determined after washing w1th water~

FungusLimiting value in kg of active ingre-dient/m3 of pine _ Coniophora puteana 1.4 - 2.2 Poria ~onticolao.s Lenzites trabea0.5 Coriolus versico1or l.o - 1.6 ' ~

Claims

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:

1. A method of controlling wood-damaging fungi, wherein the fungi, or the wood threatened by fungal infestation, excluding wood from rubber trees, is treated with a fungicidally effective amount of N-tridecyl-2,6-dimethylmorpholine, except in the form of an aqueous solution which contains a 1,3-butadiene polymer as solubilizer.

2. The method of claim 1, wherein the amount of N-tridecyl-2,6-dimethylmorpholine used for the treatment is of 0.5 to 8 g per square meter of wood surface.