Wood preservative oxathiazines

Details Wood preservative oxathiazines Wood preservative oxathiazines

1997-11-12

2002-04-16

Barr, Michael (Department: 1762)

Coating processes

Immersion or partial immersion

Cellulosic base

C427S004000

Reexamination Certificate

active

06372297

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a process for preserving wood and composite wood materials from wood damaging organisms, and compositions useful in such process.
This invention more specifically is directed to a class of 3-aryl-5,6-dihydro-1,4,2-oxathiazines and their oxides which are useful against such wood damaging organisms as bacteria, yeasts, and fungi.
This invention is also directed to novel 3-aryl-5,6-dihydro-1,4,2-oxathiazines and their oxides which are useful against such wood damaging organisms as bacteria, yeasts, and fungi.
2. Description of Related Art
The preservation of wood is a subject of great economic importance. For most purposes, untreated wood is entirely unsatisfactory. It will twist, warp, and crack as it dries; it cannot easily be glued or finished, and it is subject to attack of fungi and/or insects. Properly prepared and preserved wood possesses strength and incompressibility while being flexible.
U.S. Pat. No. 4,569,690 refers to various 3-aryl-5,6-dihydro-1,4,2-oxathiazines and their oxides said to be useful as herbicides, plant fungicides, plant dessicants and defoliants. No mention is made of preserving wood materials from damaging organisms.
Chemical Abstracts 103(1):2144u refers to fungicides containing phenyl-alpha-chloroacetamides said to be effective in industrial environments including paints, metal cutting fluids, and to prevent the growth of cellulose degrading fungus on treated wood.
Chemical Abstracts 102(16):133786g refers to resistance to biological attack in wood treated with epoxides. U.S. Pat. No. 4,562,185 refers to 1-oxo-3-aza-cyclopentane derivatives said to be useful as pesticides, especially systemic insecticides, effective against acarids and nematodes and showing residual activity on wood and clay.
U.S. Pat. No. 4,067,862 refers to a process for modification of polymeric materials with a nitrile sulfide. The modified polymers are said to have uses including decorative or protective coatings for wood.
World Patents Index 67-05105G/00 refers to fungicidal 2-mono substituted amino 1-azacycloalkene-1 compounds, said to have fungicidal activity in both plants and other organic materials including wood.
U.S. Pat. No. 4,977,186 refers to wood preservative and soil treatment compositions containing carbamates.
SUMMARY OF THE INVENTION
This invention relates to a compound of the formula
wherein n is 0, 1 or 2; R
1
is hydrogen, C
1
-C
4
linear or branched alkyl, or benzyl; and
Q is:
wherein R
2
, R
3
and R
4
are, individually, hydrogen, alkyl, alkoxy, alkylthio, alkoxycarbonyl, halogen, trihalomethyl, cyano, acetyl, formyl, benzoyl, nitro, alkoxyaminomethyl, phenyl, or phenylaminocarbonyl, wherein the alkyl or alkoxy moieties are all C
1
-C
4
, linear or branched, with the proviso that at least one of R
2
, R
3
or R
4
must be other than hydrogen;
wherein R
5
, R
6
and R
7
are, individually, hydrogen, C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, halogen, trihalomethyl, cyano, acetyl, formyl, benzoyl, nitro, phenyl, or phenylaminocarbonyl, with the proviso that at least one of R
5
, R
6
or R
7
must be other than hydrogen;
wherein R
8
, R
9
and R
10
are, individually, hydroxyl, halo, C
1
-C
12
alkyl, C
5
-C
6
cycloalkyl, trihalomethyl, phenyl, C
1
-C
5
alkoxy, C
1
-C
5
alkylthio, tetrahydropyranyloxy, phenoxy, (C
1
-C
4
alkyl)carbonyl, phenylcarbonyl, C
1
-C
4
alkylsulfinyl, C
1
-C
4
alkylsulfonyl, carboxy or its alkali metal salt, (C
1
-C
4
alkoxy)carbonyl, (C
1
-C
4
alkyl)aminocarbonyl, phenylaminocarbonyl, tolylaminocarbonyl, morpholinocarbonyl, amino, nitro, cyano, dioxolanyl, or (C
1
-C
4
alkoxy)iminomethyl; or
 wherein X is oxygen or sulfur; Y is nitrogen, —CH—, or —C (C
1
-C
4
alkoxy)—; and R″ is hydrogen or C
1
-C
4
alkyl.
The compounds of the present invention are useful for the long-term preservation of wood and composite wood materials against wood damaging and wood destroying materials.
The present invention also provides methods useful for the long-term preservation of wood and composite wood materials against wood damaging and wood destroying materials. For the purpose of this invention, a composite wood material is any product made from wood, including, but not limited to, plywood, pressed wood, chipboard, particle-board, wafer board, wood laminated material and the like.
In accordance with the present methods, a wood material is preserved by treatment with a fungicidally or bactericidally effective amount of an active agent represented by the formula below
wherein n is 0, 1 or 2; R
1
is hydrogen, C
1
-C
4
linear or branched alkyl, or benzyl; and
R is:
(a) phenyl; naphthyl; phenyl substituted with 1-3 of the following substituents:
hydroxyl, halo, C
1
-C
12
alkyl, C
5
-C
6
cycloalkyl, trihalomethyl, phenyl, C
1
-C
5
alkoxy, C
1
-C
5
alkylthio, tetrahydropyranyloxy, phenoxy, (C
1
-C
4
alkyl)carbonyl, phenylcarbonyl, C
1
-C
4
alkylsulfinyl, C
1
-C
4
alkylsulfonyl, carboxy or its alkali metal salt, (C
1
-C
4
alkoxy)carbonyl, (C,-C
4
alkyl)aminocarbonyl, phenylaminocarbonyl, tolylaminocarbonyl, morpholinocarbonyl, amino, nitro, cyano, dioxolanyl, or (C
1
-C
4
alkoxy)iminomethyl;
pyridinyl; thienyl, preferably when n is not 2; furanyl; or thienyl or furanyl substituted with 1 to 3 of the following groups:
alkyl, alkoxy, alkylthio, alkoxycarbonyl, halogen, trihalomethyl, cyano, acetyl, benzoyl, nitro, formyl, alkoxyaminomethyl, phenyl, or phenylaminocarbonyl, wherein the alkyl or alkoxy moiety is C
1
-C
4
, linear or branched; or
 wherein X is oxygen or sulfur; Y is nitrogen, —CH—, or —C (C
1
-C
4
alkoxy)—; and R″ is hydrogen or C
1
-C
4
alkyl.
In further accordance with the present invention, there is provided a composition comprising a) a wood preservative amount of a compound of formula I or II, and b) a suitable carrier.
DETAILED DESCRIPTION OF THE INVENTION
A preferred embodiment of the compounds of this invention are those compounds of formula I wherein R
1
is hydrogen or C
1
-C
4
alkyl; n is 1 or 2; R
2
, R
3
and R
4
are, individually, hydrogen, C
1
-C
4
alkyl, halo, (C
1
-C
4
alkoxy)—carbonyl, or cyano, with the proviso that at least one of R
2
, R
3
and R
4
must be other than hydrogen; R
5
, R
6
and R
7
are, individually, hydrogen, halo or cyano, with the proviso that at least one of R
5
, R
6
and R
7
must be other than hydrogen; R
8
, R
9
and R
10
are C
1
-C
4
alkyl, C
1
-C
4
alkoxy, nitro, halo, trihalomethyl, or (C
1
-C
4
alkoxy)—carbonyl; X is sulfur; and R″ is hydrogen.
More preferred are those compounds of formula I wherein R
1
is hydrogen; n is 1 or 2; R
2
, R
3
and R
4
are, individually, hydrogen, methyl, ethyl, bromo, chloro, ethyl carboxylate, or cyano, with the proviso that at least one of R
2
, R
3
and R
4
must be other than hydrogen; R
5
, R
6
and R
7
are, individually, hydrogen, bromo, chloro or cyano, with the proviso that at least one of R
5
, R
6
and R
7
must be other than hydrogen; R
8
, R
9
and R
10
are methyl, ethyl, nitro, fluoro, chloro, or trifluoromethyl.
In a preferred embodiment of the method of the present invention, the compounds of structure II are substituted with R
1
being hydrogen, n being one or two, and R has one or 2 of the following values:
phenyl, (C
1
-C
6
alkyl)phenyl, halophenyl, dihalophenyl, biphenyl, (C
1
-C
5
alkyloxy)phenyl, trihalomethylphenyl, nitrophenyl, phenyl substituted with (C
1
-C
4
alkoxy)carbonyl, furanyl, furanyl substituted by ethyl carboxylate, cyano, chlorine, or bromine, thienyl, thienyl substituted with ethyl carboxylate, cyano, chlorine, or bromine, or (C
1
-C
6
alkyl)nitrophenyl.
In a still further preferred embodiment of the method of this invention, R
1
is hydrogen, n is one or two, and R is represented by:
4-chlorophenyl, 3-nitrophenyl, 3,4-dichlorophenyl, 3-fluorophenyl, 2-thienyl, 4-methylphenyl, 3-trifluoromethylphenyl, 3-ethanonephenyl, 3,5-dichlorophenyl, 4-trifluoromethylphenyl, 3-methyl-4-nitrophenyl.
In another preferred embodiment of the method of this invention, R
1
is hydrogen, and R is

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