Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1998-11-12
2001-04-03
Dees, Jose′ G. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
Reexamination Certificate
active
06211218
ABSTRACT:
It is known that dimethylalkylamines, for example in the form of salts of long-chain monocarboxylic acids, can be used for application in oily, solvent-containing wood preservatives (EP 147 976). The same applies to mixtures of fenpropimorph and water-insoluble acids (EP-B-0 402 697).
It is also known that dimethylalkylamine, tridemorph, fenpropimorph or their mixture, an emulsifier and a water-insoluble acid can be used as water-soluble wood preservatives (EP-A-0 370 371).
It is also known that dimethylalkylamine, tridemorph, fenpropimorph, and a water-soluble acid can be used as water-soluble concentrates in wood preservation (DE-A-3 736 298).
Mixtures based on dimethyl-coconut fatty amine, 2-ethylhexanoic acid, propiconazole and an emulsifier have also been described for use as wood preservatives.
However, these water-soluble wood preservatives have considerable disadvantages in application. They have a corrosive effect on iron and steel and dissolve, inter alia, rust and other iron compounds from the surfaces of the impregnation tank with formation of emulsifiable or water-soluble iron salts, so that application solutions acquire a strong brown discoloration in a short time. Consequently, the wood to be impregnated is in turn influenced in its color and is changed, resulting, for example, in a strong gray discoloration owing to reaction of the iron compounds with wood constituents. At the same time, the pH of the application solution increases; the result may be instability of the solutions, including phase separation.
It has now been found that the performance characteristics of the water-soluble wood preservatives are considerably improved if wood preservatives which contain a dimethylalkylamine, an aliphatic C
8
-C
20
-dicarboxylic acid and a triazole compound are used. In addition to the excellent performance characteristics, the wood preservatives have very good activity against wood-destroying Basidiomycetes.
The novel wood preservatives (concentrates) are water-miscible and, on dilution of the concentrates with water, form clear to slightly opaque solutions. Advantageously, the aqueous solutions (impregnating solutions) obtained after dilution of the concentrates with water have a pH of from 4 to 8, preferably from 5 to 7. The aqueous impregnating solutions obtained are distinguished by the fact that the active components penetrate very effectively into the wood to be impregnated and thus result in effective wood preservation.
A dimethylalkylamine is an N,N-dimethyl-N-alkylamine whose alkyl radical contains, for example, 6 to 20 carbon atoms. Dimethylalkylamines having 12 or 14 carbon atoms in the alkyl radical are preferred. In addition to the pure dimethylalkylamines, mixtures, for example mixtures of dimethyl-C
12
-alkylamine and dimethyl-C
14
-alkylamine (dimethyl-(C
12
/C
14
-alkylamine), may also be used.
The novel wood preservatives contain C
8
-C
20
-dicarboxylic acid, preferably C
8
-C
14
-dicarboxylic acids. Suitable dicarboxylic acids are, for example, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, brassylic acid and thapis acid. Sebacic acid is particularly advantageously used.
Examples of suitable triazoles are: (Z)-2-(1,2,4-triazol-1-ylmethyl)-2-(4-fluorophenyl)-3-(2-chlorophenyl)oxirane (epoxiconazole), 2-(1-chlorocyclopropyl-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)-propan-2-ol, 1-butyl-1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)ethanol (hexaconazole), 1-[2-chlorophenyl)methyl]-1-(1,1-dimethyl)-2-(1,2,4-triazol-1-yl-ethanol, 1-(4-fluorophenyl)-1-(2-fluorophenyl)-2-(1,2,4-triazol-1-yl)-ethanol (flutriafol), (RS)-4-(4-chlorophenyl)-2-phenyl-2-(1H-1, 2,4-triazol-1-yl-methyl)butyronitrile, 1-[(2 RS, 4RS; 2 RS, 4 SR)-4-bromo-2-(2,4-dichlorophenyl)tetrahydrofurfuryl]1H-1,2,4-triazole, 3-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)quinazolin-4(3H)-one, (RS)-2,2-dimethyl-3-(2-chlorobenzyl)-4-(1H-1,2,4-triazol-1-yl)butan-3-ol, bitertanol, triadimefon, triadimenol, cyproconazole, dichlobutrazol, difenoconazole, diniconazole, etaconazole, flusilazole, penconazole, tetraconazole, bromuconazole, metconazole, fenbendazol, fensilazol, 1-(2-(2,4,-dichlorophenyl)-1,3-dioxolan-2-ylmethyl)-1H-1,2,4-triazole (azaconazole), 1-(2-(2, 4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl-methy)-1H-1,2,4-triazole (propiconazole), &agr;-tert-butyl-a-(p-chlorophenyl-ethyl)-H-1,2,4-triazole-1-ethanol (tebuconazole).
Propiconazole, penconazole, cyproconazole, hexaconazole and tebuconazole are particularly advantageously used.
Triazoles may be present not only in the form of the free base but also in the form of a metal salt complex or as an acid addition salt.
In order to improve the fungicidal activity, it may be advantageous if the novel wood preservative additionally contains morpholine derivatives, preferably the fungicidal active ingredients fenpropimorph (4-[3-(4-tert-butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine), fenpropidin (N-[3(4-tert-butylphenyl)-2-methylpropyl]piperidine or tridemorph (N-tridecyl-2,6-dimethylmorpholine) or salts thereof.
A synergistic improvement in activity is achieved as a result. Fenpropimorph is particularly advantageously used. Fenpropimorph, fenpropidin or tridemorph and the triazoles are preferably used in a weight ratio of from 0.5:1 to 10:1, preferably from 1:1 to 5:1, in particular from 2:1 to 3:1.
It may furthermore be advantageous if the novel wood preservative additionally contains a water-insoluble monocarboxylic acid or a salt thereof.
Suitable water-insoluble monocarboxylic acids are, for example, a straight-chain aliphatic monocarboxylic acid of 5 to 20 carbon atoms, such as hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid or decanoic acid, or a branched aliphatic monocarboxylic acid, such as 2-ethylhexanoic acid, 2-ethylheptanoic acid, isooctanoic acid, isoheptanoic acid, isononanoic acid, versatic acid or neocarboxylic acid (more highly branched monocarboxylic acids). Other water-insoluble monocarboxylic acids, eg. sorbic acid, benzoic acid, or cyclohexanecarboxylic acid, may also be used. 2-Ethylhexanoic acid is particularly advantageously used.
The novel wood preservatives may additionally contain boron compounds, eg. boric acid, alkali metal borates or boric esters, as diffusable components. This additionally results in an improvement in the activity in the protection from blue rot and mold.
The novel wood preservatives (concentrates) contain in general from 5 to 65, in particular from 25 to 55%, by weight of dimethylalkylamine, in particular dimethyl-(C
12
/C
14
)alkylamine, from 0 to 35, in particular from 5 to 20%, by weight of morpholine derivatives, in particular fenpropimorph, from 0.25 to 15, preferably from 1 to 10, in particular from 2.5 to 7.5, % by weight of triazole, from 2.5 to 35, in particular from 10 to 25, % by weight of aliphatic C
8
-C
20
-dicarboxylic acids, in particular sebacic acid, from 0 to 30, in particular from 2.5 to 12.5%, by weight of water-insoluble monocarboxylic acids, from 0 to 30% by weight of water and from 0 to 30% by weight of organic solvents,
the sum in each case being 100% by weight. Water and solvents serve here, inter alia, for better handling, for example adjustment of the viscosity, acceleration of the dissolution of the concentrates in water. Some of the solvents are simultaneously required for dissolving the triazoles.
The concentrates obtained may be present in liquid homogeneous form, as a paste or in solid form.
Preferably used organic solvents are water-soluble or water-miscible polar solvents, for example glycols (ethylene glycol, propylene glycol), glycol ethers (ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, glycol ether acetates (butylglycol acetate), N-alkylpyrrolidones (N-methylpyrrolidone), alcohols, dimethylformamide, acetylformamide and dimethyl sulfoxide.
Hydroxycarboxylic acids, eg. tartaric acid or maleic acid, may be added to the concentrates or impregnating solutions in order to establish the pH, for example of about 6 or lower.
In order to increase the
Goettsche Reimer
Kardorff Uwe
Kober Reiner
BASF - Aktiengesellschaft
Dees Jose′ G.
Keil & Weinkauf
Pryor Alton
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