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Патент USA US3090732

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3£90J22
Patented May 21, 1963
1
2
3,090,722
Illustrative of the organomercury compounds within
the scope of the compositions of this invention are the
STABILIZATION 0F ALEHATI€ MERCURY
FUNGICEES
Harris M. Baker, Glen Farms, Md, assignor to E. I. du
Pont de Nemours and Company, Wihnington, Dei., a
corporation of Delaware
following:
Methylmercury acetate
Ethylmercury acetate
No Drawing. Filed Jan. 24, 1961, Ser. No. 84,495
21 Claims. (Cl. 16’7—42)
This invention relates to fungicidal compositions con 10
taining aliphatic mercury compounds and to the stabil
ization of such compositions.
Fungicidal compositions and seed treatment composi
tions containing aliphatic mercury compounds and a
rhodamine dye are well known in the art. Such composi
tions are useful, for example, in the treatment of seeds
to protect the seeds against soil borne or seed borne or
ganisms. The dye is an essential part of such composi
Ethylmercury phosphate
Isopropylmercury propionate
Methylmercury butyrate
Isopropylmercury phosphate
Ethylmercury-2,3-dihydroxypropyl mercaptide
thylrnercury hydroxyacetate
Methylmercury 3-hydroxypropionate
S-hydroxypropylenebis (methylmercury mercaptide)
3~hydroxypropylenebis (ethylmercury mercaptide)
Ethylmercury-N-ethyl-methanesulfonamide
Methylmercury-N-methyl-rnethanesulfonamide
Methyimercury dicyandiamide
Methylmercury nitrile
tions to mark the treated seed, and thus to prevent in
n-Butylmercury nitrile
advertent use of such treated seed for feed purposes.
20 Methylmercury hydroxide
These compositions are liquids which have the dis
Isobutylmercury hydroxide
advantage of tending towards sludge formation, particu
larly when prepared and/ or stored at comparatively low
temperatures. This sludge formation has long been a
recognized problem in the trade. Although considerable 25
effort has been expended in an attempt to solve this prob
lem, no satisfactory solution to the problem has been
found prior to the present invention.
Isobutylmercury phosphate
Methylmercury-N-ethyl-ethanesulfonamide
Methylmercury-2,3-dihydroxypropyl mercaptide
Ethylmercury-2,3,4,5,6-pentahydroxyhexyl mercaptide
Methylmercury-E~hydroxyquinolinate
n-Propylmercury nitrile
n-Propylrnercury 2-hydroxy-3-chloropentyl mercaptide
Isopropylmercury 2,5-dihydroxypentyl mercaptide
Methylmercury 3,4,5-trihydroxyhexyl mercaptide'
According to the present invention, undesirable sludge
formation in compositions containing an aliphatic mer
cury compound and rhodamine B base is inhibited by
As stated above, admixture of a rhodamine dye to
gether with the aliphatic mercury salt has been known
to be advantageous. However, the problem of sludge
amines has been found to reduce or inhibit sludge forma
formation
in these compositions has made their usage less
35
tion whereas other amines are unsuccessful in inhibiting
than completely satisfactory. This is particularly true
sludge formation.
when the composition is prepared, or stored, or both
The aliphatic mercury compound which is the fungi
prepared and stored, under low temperature conditions
cidally active ingredient in the non-sludging compositions
for a long period of time. Thus, when the compositions
of this invention can be represented by the structure
the inclusion therein of a dialkanolamine or a trialkanol
amine. For some reason, this narrow class of alkanol
40 are exposed for an extended period of time to tempera
tures on the order of —20° to 5 or 10° C., such as typi
cally happens in winter storage in northern climates,
where R is an aliphatic radical having less than 7 carbon
atoms, i.e., 1, 2, 3, 4, 5, or 6 carbon atoms, an X is a
negative radical well known as a substituent in organe
rnercury fungicidal compounds, such as phosphates, di
such as a period of weeks or months, the undesirable
sludge formation occurs.
45
According to the present invention, the third essential
ingredient in admixture with the aliphatic mercury com
cyandiamides, S-hydroxyquinolinates, nitriles, mercap
tides, hydroxides, lower alkyl sulfonamides, lower alkyl
carboxylic acids, and lower hydroxyalkyl carboxylic acids.
from the group including di-ethanolamine, triethanol
It has been observed that especially advantageous re
sults are achieved when the aliphatic mercury compound
amine and tri-butanolamine.
is a lower alkyl-mercury salt of a hydroxy-substituted
lower-alkyl mercaptan of the formula
pound and the rhodamine B base is an alkanolamine
amine, di-propanolamine, tii-propanolamine, di-butanol
cially preferred.
Triethanolamine is espe
Mixtures of these sludge inhibiting alkanolamines can
of course be used.
The sludge inhibiting alkanolamine will be used in
an amount sul?cient to prevent or inhibit sludge forma
where R is methyl, ethyl, n-propyl, isopropyl, n-butyl,
isobutyl, or tert-butyl; n is a positive whole integer less
than 3, i.e., 1 or 2; and R1 is a hydrox -substituted lower
alkyl ‘or alkylene radical containing from 2 through 6
tion. The exact amount will depend upon the sludge
forming tendency of the other ingredients in the com~
position, as well as the conditions for preparation and
storage for the composition. Generally, an amount of
carbon atoms, and having 1, 2, 3, 4 or 5 OH groups. It
will be understood that R1 is monovalent when n is 1
from about 1 to 10% of the sludge inhibiting alkanol
and divalent when n is 2; and also that no more than one
tated by circumstances.
OH group or RHgS group is attached to a single carbon
atom.
amine will be used, but more or less can be used as dic
Use of the narrow class of alkanolamines to inhibit
sludge formation in the compositions of this invention is
3,090,722
4
3
ingredients into a fungicidal composition of the follow
believed to be the only satisfactory method of sludge
inhibition, aside from the only known method heretofore
known, namely the use of highly expensive, highly pure,
ing ingredients:
Percent
Ethylmercury-N-ethyl-methanesulfonamide _____ __
re?ned starting materials not easily available commer
cially. Practice of the present invention therefore .per
mits the use of less expensive, commercially available
starting materials without cost penalty.
The compositions of this invention, in addition to the
three essential ingredients recited above, will usually con
tain other ingredients such as water, methanol, ‘ethanol,
15.0
Ethylene glycolmonoethyl ether _______________ __ 35.0
Diethanolamine
4.0
Water plus impurities _______________________ __. 42.0
This fungicidal composition is free of sludge when pre
pared and no signi?cant amount of sludge forms when the
material is stored at low temperatures for an extended
period of time.
glycol, ethyleneglycol, dimethylformamide, glycerol, or
Example 3
‘The compound methylmercury dicyandiamide is for
other suitable solvents chosen according to the needs of 15
the particular system, as will be readily understood in the
art. The compositions can optionally also contain inor
mulated into a fungicidal composition of the following
ingredients:
ganic salts, surfactants, ammonia, sodium hydroxide, as
'
Percent
well as other adjuvants, buffers or other organic or inor
Methylmercury dicyandiamide _____________ _Y____' 8.0
ganic substituents. ‘Some of these ingredients are present
Rhodamine B base
when normal commercially available starting materials,
_
25
The solvents chosen for use in the compositions will
generally be those which will lend to the composition the
property of having a ?ash point greater than 80°
Normally, the compositions of this invention will con
tain by weight from about 1% to about 15% of the ali
phatic mercury compound, from about 0.2% to about 6%
of rhodamine B base, and from about 1 to 10% of the al
66.0
10.0
When this formulation is stored at low temperatures,
no signi?cant amount of sludge forms.
Example 4
The compound n-ibutylmercury nitrile is formulated
into a fungicidal composition containing the following
ingredients:
Percent
kanolamine, the balance of the composition comprising
solvent, inorganic salts, impurities, and the like, as men
tioned above.
The various components of the composition can be
admixed in any order as convenient. Ordinarily, the al
n-Butylmercury nitrile _______________________ __
Rhodamine B base __________________________ __
1.0
.2
Tri-n-butanolamine _________________________ __
1.0
Dimethylformamide ________________________ __ 77.8
kanolamine will be incorporated in the composition be
fore the aliphatic mercury compound and rhodamine B
Water plus impurities ___________________ _,.____ 20.0
When this composition is prepared no signi?cant
40
amount of sludge forms and no sludge forms when the
composition is stored at low temperatures for an extended
The following examples are illustrative of the present
invention. The percent ?gures indicated are by weight.
period of time.
Example 5
Example 1
45
The following composition is formed by liquid blend
ing of the components:
Ethylmercury acetate ________________________ __
.
Ethyleneglycol
Sodium nitrite
Rhodamine B base
____
___
__
Triethanolamine
Percent
Isobutylmercury hydroxide ___________________ __
5.0
1.3
Rhodamine B base
3.0
12.0
Diethylene glycol-
Ethylmercury-Z,3-dihydroxypropy1 mercaptide_____ 6.0 50
_
Isobutylmercury hydroxide is formulated into a pes
ticidal composition containing the following ingredients:
Percent
__
6.0
Diethylene glycol
Glycerol
aid in extending the treatment over the surface of the seed,
Ethanol
‘
Diisopropanolamine _______________________ _;_ 10.0
over which little control can be exercised, are used, while
some of the others might be added to inhibit corrosion, to
base, but this is not essential.
1.5
Methanol
diethyleneglycolmonoethyl ether, diethyleneglycolmono
methyl ether, propanol, isopropanol, ethyleneglycolmono
ethyl ether, ethyleneglycolmonomethyl ether, diethylene
or the like.
2.5
Rhodamine B base __________________________ __
__ 40.0
1.5
2.0 55
5.0
The balance of the composition is water and unidenti
Isopropanol
_..._
20.0
40.0
Triisopropanolarnine
‘ _______________________ _._
5.0
Water plus impurities ____________________ __'___. 27.0
No signi?cant amount of sludge forms when this com
position is prepared and stored at low temperature.
Example 6
The compounds methylmercury monothioglycol and
fled impurities normally associated with commercially
available starting materials used in the preparation of the 60
methylmercury acetate are formulated into a fungicidal
composition as follows:
This composition upon storage at room temperature,
or at controlled 5° C. temperature, or even as low as
Percent
—2-5‘’ 0., for a period of several months, evidences no
Methylmercury acetate ______________________ __
1.0
composition.
sediment or sludge formation.
65 Methylmercury monothioglycol _______________ __
By comparison, an identical formulation prepared in
an identical manner except that the 5% triethanolamine is
replaced with water, shows a highly objectionable sludge
Ethylene glycol___
formation developing within two to three weeks after
70 Di-n-butanolamine
storage at 5° C. and —25° C.
Example 2
The ‘I compound ethylmercuryaN-ethyl-methanesulfon
amide 1s formulated by simple blending of the indicated 75
5.0
Rhodamine B ‘base _________________________ __ 2.5
Ethyleneglycolmonomethyl ether ______________ __ 15.0
Methanol
__
10.0
30.0
_________________________ __
3.0
Water plus impurities _______________________ __ 33.5 .
No signi?cant amount of sludge forms when this com
position is prepared and when it is stored at low tempera
tures.
'
3,090,722
5
6
Example 7
The compound isopropylmercury phosphate is formu
wherein
' R is an aliphatic radical of 1 through 6 carbon atoms
and
lated into a fungicidal composition as follows:
X is selected from- the group consisting of phosphates,
dicyandiamides, 8-hydroxyquinolinates, nitriles, mer
captides, hydroxy-substituted lower alkyl and alkyl
ene mercaptans, hydroxides, lower alkyl sulfon
amides, lower alkyl carboxylic acids and lower hy
Percent
Isopropylmercury phosphate __________________ __ 10.0
Rhodarnine B base
4.0
Di secondary butanolamine ___________________ .._ 8.0
Diethyleneglycolmonomethyl ether ____________ __ 60.0
Ethanol
12.0 10
Water plus impurities
droxyalkyl carboxylic acids, said composition ad
ditionally containing from about 0.2% to 6% by
6.0
weight of rhodamine B base and a sludge inhibiting
When this composition is prepared and stored at low
temperatures, no signi?cant amount of sludge forms.
amount of at least one compound selected from the
group consisting of (1) di-alkanolamines wherein
Example 8
15
Methylmercury-N-methyl-methanesulfonamide is formu
lated into a fungcidal composition as follows:
Percent
Methylmercury-N-methyl-methanesulfonamide ____ 15.0 20
Rhodamine B base _________________________ __
the alkanol has from 2 to 4 carbon atoms inclusive
and (2) tri-alkanolamines wherein the alkanol has
from 2 to 4 carbon atoms inclusive.
2. A fungicidal composition comprising as essential
ingredients 1% to 15% by weight of a fungicidal aliphatic
mercury compound of the formula:
R—Hg—X
6.0 '
Dimethylformamide ________________________ __ 74.0
wherein
Diethanolamine _
5.0
R is an aliphatic radical of 1 through 6 carbon atoms
and
When this formulation is prepared and stored at low
X is selected from the group consisting of phosphates,
temperatures, no signi?cant amount of sludge develops. 25
dicyandiamides, 8-hydroxyquinolinates, nitriles, mer
captides, hydroxy-substituted lower alkyl and alkyl
Example 9
Methylmercury - 2,3 - dihydroxypropyl mercaptide
ene mercaptrans, hydroxides, lower alkyl sulfon
is
formulated into a fungicidal composition containing the
following ingredients:
30
Percent
Methylmercury-2,3-dihydroxypropyl mercaptide___ 4.0
Rhodamine B base
1.0
Propanol
Ethyleneglycol
10.0 M
____________________________ __ 40.0 a”
Diethanolamine
Water plus impurities
4.0
4.1.0
amides, lower alkyl carboxylic acid and lower hy
droxyalkyl carboxylic acids, said composition addi
tionally containing from about 0.2% to 6% by
Weight of rhodamine B base and from about 1% to
10% by weight of a compound selected from the
group consisting of (1) dialkanolamines wherein the
alkanol has from 2 to 4 carbon atoms inclusive and
(2) tri-alkanolamines wherein the alkanol has from
2 to 4 carbon atoms inclusive.
3. A fungicidal composition comprising as essential
ingredients from about 1% to 15% by weight of a com
amount of sludge forms and no appreciable amount of 40 pound of the formula:
sludge forms when the composition is stored at low
When this composition is prepared, no appreciable
R—Hg—X
temperatures.
Example 10
The compound methylmercury-8-hydroxyquinolinate is 45
formulated into a fungicidal composition containing the
captides, hydroxy-substituted lower alkyl and alkyl
Percent
Methylmercury-S-hydroxyquinolinate
_________ __
_
:ene mercaptans, hydroxides, lower alkyl sulfonam~
2.0
1.0 5°
Diethyleneglycolmonoethyl ether ______________ __ 50.0
Isopropyl alcohol
Triisopropanolamine
10.0
_______________________ __
ides, lower alkyl carboxylic acids and lower hy
droxyalkyl carboxylic acids, said composition addi
tionally containing from about 0.2% to 6% by weight
of rhodamine B base and from about 1% to 10%
6.0
Water plus impurities ________________________ __ 31.0 55
by weight ‘of 'diethanolamine.
4. A fungicidal composition comprising as essential
ingredients from about 1% to 15% by weight of a com
No signi?cant amount of sludge forms when this com
position is prepared or when it is stored at low tempera
pound of the formula:
R—Hg—X
tures.
Example 11
wherein
The compound ethylmercury-N-methylmethanesulfon- 60
amide is formulated as in Example 5. No signi?cant
amount of sludge forms when this formulation is pre
pared or when it is stored at low temperatures.
Example 12
65
1 The invention claimed is:
1. A fungicidal composition comprising as essential
ingredients 1% to 15% by weight of a compound of the
formula:
R is an aliphatic radical of 1 through 6 carbon atoms
and
' X is selected from the group consisting of phosphates,
idicyandiamides, S-hydroxyquinolinates, nitriles, mer
captides, hydroxy-substituted lower alkyl and alkyl
ene mercaptans, hydroxides, lower alkyl sulfonam
ides, lower ‘alkyl carboxylic acids and lower hy
droxyalkyl carb-oxylic acids, said composition addi—
tiorrally containing from about 0.2% to 6% by
The compound methylmercury nitrile is formulated as
in Example 8. No signi?cant amount of sludge forms
when this composition is prepared or when it is stored
at low temperatures.
'
R is an aliphatic radical of 1 through 6 carbon atoms
and
X is selected from the ‘group consisting of phosphates,
ldicyandiamides, 8-hydlroxyquino-linates, nitriles, mer
following ingredients:
Rhodarnine 13 base
wherein
70
weight of rhodamine B base and from about 1% to
about 10% by weight of triethanolamine.
5. A ‘fungicidal composition comprising as essential
ingredients from about 1% to 15% ‘by weight of a com
pound of the formula:
3,090,722
3
7
wherein
tionally containing from about 0.2% to 6% by
' ’
weight of rhodamine B base and from about 1%-to
' R is an‘aliphatic radical of 1 through 6 carbon atoms
and
10% ‘by weight of di-sec-butanolamine.
i
'
10. A fungicidal composition comprising from about
X is selected from the group consistingof phosphates,
dicyandiamides, S-hydroxyquinolinates, nitriles, mer 5 1% to 15 % by weight of methylmlercury 2,3-dihydroxy
propyl mercaptide, from about 0.2% to 6% by weight
captides, hydroxy-substituted lower alkyl and alkyl
of rhodamine B base and from about 1% to 10% by
ene mercaptans, hydroxides, lower alkyl sulfonam
weight of tri-ethanolamine.
ides, lower alkyl carboxylic acids and lower by
11. A fungicidal composition comprising from 1% to
droxyalkyl carboxylic acids, said composition addi
tionally containing from about 0.2% to ‘6% by 10 15% by’ weight of ethylmercury 2,3~dihydroxypropyl
mercaptide, from about 0.2% ~ to 6% by weight of
‘weight of rhodamine B base and from about 1% to
rhodamine B base and from about 1% to 10% by weight
10% by weight of =di-iso-propanolamine.
6. A fungicidal composition comprising as essential
of tri-‘ethanolamine.
12. A fungicidal composition comp-rising from about
ingredients from about 1% to 15% by weight of a com
15 1% ‘to 15 % by weight of methylmercury 2,3-dihydroxy
pound of the formula:
pnopyl mercaptide, from about 0.2% to 6% by weight
V
R-Hg-X
of rhodamine ‘B base and from about 1% to 10% by
wherein
weight of di-iso-propanolamine.
R is an aliphatic radical of 1 through 6 carbon atoms
13. A fungicidal composition comprising from about
and
‘
20 1% to 15% by weight of ethyimercury 2,3-dihydroxy
X is selected from the group consisting of phosphates,
propyl mercaptide, from about 0.2% to 6% by weight
dicyandiamides, S-hydroxyquinolinates, nitriles, mer
of rhodamine B base and from about 1% to 10% by
captides, hydroxy-substituted lower alkyl and alkyl
weight
of di-iso-propanolamine.
ene mercaptans, hydroxides, lower alkyl sulfonarn
' 14. A method of inhibiting sludge formation in a
ides, lower alkyl carboxylic acids and lower hy
fungicidal composition containing 1% to 15 % by weight
droxyalkyl carboxylic acids, said composition addi
of a compound of the ‘formula:
tionally containing from about 0.2% to 6% by
weight of rhodamine B base and from about 1% to
10% by weight of tri-iso-propanolamine.
7. A fungicidal composition comprising as essential 30
ingredients from about 1% to 15% by weight of a com
pound of the formula:
R—Hg-~X
wherein
‘R is an aliphatic radical of 1 through 6 carbon atoms
and
X is selected from the group consisting of phosphates,
dicyandiamides, Sbydroxyquinolinates, nitriles, mer
captides, hydroxy-substituted lower alkyl and alkyl
wherein
R is an aliphatic radical of 1 through 6 carbon atoms 35
and
X is selected from the group consisting of phosphates,
dicyandiamides, 8-hydroxyquinolinates, nitriles, mer
captides, hydroxy-substituted lower alkyl and alkyl
ene mercaptans, hydroxides, lower alkyl sulfon
amides, lower alkyl carboxylic acids, and lower hy
droxyalkyl carboxylic acids; and 0.2% to 6% by
tionally containing from about 0.2% to 6% by
weight of rhodamine B base, comprising incorpo- '
rating therein a sludge inhibiting amount of at least
one compound selected from the ‘group consisting
of (1) idi-alkanolamines wherein the alkanol has
from 2 to 4 carbon atoms inclusive and (2) tri
alkanolamines wherein the alkanol has ‘from 2 to 4
weight of rhodamine B base and from about 1% to
carbon atoms inclusive.
ene mencaptans, hydroxides, lower alkyl sulfonam 40
ides, lower alkyl carboxylic acids and lower hy
droxyalkyl carboxylic acids, said composition addi
.
V
45
10% by weight of di-n-butanolamine.
15. A method of inhibiting sludge formation in a
8. A fungicidal composition comprising as essential
fungicidal composition containing from about 1% to 15 %
ingredients from about 1% to 15 % by weight of a com
by weight of a compound of the formula:
pound of the formula:
R—Hg——X
wherein
R is an aliphatic radical of 1 through 6 carbon atoms
50 wherein
R is an aliphatic radical of 1 ‘through 6 carbon atoms
and
X is selected from the group consisting of phosphates,
and
X is selected from the ‘group consisting of phosphates,
.dicyandiamides, S-hydroxyquinolinates, nitriles, mer~ 55
captides, hydroxy-substituted lower alkyl and alkyl
ene mercaptans, hydroxides, lower ‘alkyl sulfonam
ides, lower alkyl carboxylic acids and lower hy
droxyalkyl carboxylic acids, said composition addi
rtionally containing from about 0.2% to 6% by
weight of rhodamine B base and from about 1% to
10% by weight of tri-n-butanolamine.
16. A method of inhibiting sludge formation in a
9. A fungicidal composition comprising as essential
fungicidal composition containing from about 1% to 15 %
by weight of a compound of the formula:
ingredients from about 1% to 15 % by weight of a com- '
pound of the formula:
R—Hg-JX
dicyandiamides, S-hydroxyquinolinates, nitriles, mer
captides, hydroxy-substituted lower alkyl and alkyl
ene mercaptans, hydroxides, lower, ‘alkyl sulfon
amides, lower alkyl carboxylic acids and lower hy
droxyalkyl carboxylic acids; and from about 0.2%
to 6% by weight of rhodamine B base, comprising
incorporating therein from about 1% to 10% by
weight of di-ethanolamine.
65
wherein
R is an aliphatic radical of 1 through 6 carbon atoms
and
X is selected from the group consisting of phosphates, 70
idicyandiamides, 8-‘hyd-roxyquinolinates, nitriles, mer
R is an aliphatic radical of 1 through 6 carbon atoms"
and
s
captides, hydroxy-substituted lower alkyl and alkyl-,
X is selected from the ‘group consisting of phosphates,
dicyandiamides, S-hydroxyquinolinates, nitn'les, mer
captides, hydroxy-substituted lower alkyl and alkyl
ene mercaptans, hydroxides, lower alkyl sulfonam
ides, lower alkyl carboxylic acids and lower hy
ene mercaptans, hydroxides, lower alkyl sulfoné
amides, lower alkyl carboxylic acids and lower hy-,
droxyalkyl carboxylic acids said composition addi
rdroxyalkyl canboxylic acids; and from about 0.2% to
3,090,722
-
6% by weight of a rhodamine B base, comprising
incorporating therein ‘from about 1% to 10% by
weight of tri-ethanolamine.
10
ene mercaptans, hydroxides, lower sulfonamides,
lower alkyl carboxylic acids, ‘and lower hydroxyalkyl
carboxylic acids; and from about 0.2% to 6% by
weight of rhodamine B base, comprising incorpo
rating therein from about 1% to 10% by weight of
di-n-butanolamine.
17. A method of inhibiting sludge formation in a
fungicidal composition containing from about 1% to 15%
by weight of a compound of the formula:
20. A method of inhibiting sludge formation in a
R-——Hg-—-X
wherein
R is an aliphatic radical of 1 through 6 carbons atoms 10
fungicidal composition containing from about 1% to 15%
by weight of a compound of the formula:
R—Hg-X
and
X is selected from the group consisting of phosphates,
dicyandiamides, 8-hydroxyquinolinates, nitriles, mer
wherein
R is an aliphatic radical of 1 through 6 carbon atoms
and
captides, hydroxy-substituted lower alkyl and alkyl
ene mercaptans, hydroxides, lower .alkyl sulfon 15
X is selected from the group consisting of phosphates,
amides, lower alkyl carboxylic acids and lower hy
droxyalkyl carboxylic acids; and from about 0.2%
to 6% by weight of rhodamine B base, comprising
dicyandiamides, 8~hydroxyquinolinates, nitriles, mer
captides, hydroxy-substituted lower alkyl and alkyl
incorporating therein from about 1% to 10% by
amides, lower alkyl carboxylic acids and lower hy—
droxyalkyl carboxylic acids; and from about 0.2%
to 6% by ‘weight of rhodamine B base, comprising
incorporating ‘therein 1% to 6% by weight of Hi
weight of di-iso-propanoiamine.
ene mercaptans, hydroxides, lower alkyl sulfon
20
18. A method of inhibiting sludge formation in a
'fugicidal composition containing from about 1% to 15%
by weight of a compound of the formula:
n—butanolamine.
21. A method of inhibiting sludge \formation in a
R——Hg——-X
wherein
R is an aliphatic radical of 1 through 6 carbon atoms
and
25
fungicidal composition containing from about 1% to 157%
by weight of a compound of the formula:
R—Hg—X
X is selected ‘from the group consisting of phosphates,
wherein
dicyandiarnides, S-hydroxyquinolinates, nitriles, mer 30 R is an aliphatic radical of 1 through 6 carbon atoms
captides, hydroxy-substituted lower alkyl and alkyl
and
ene ‘mercaptms, hydroxides, lower alkyl sulfon
X is selected from the group consisting of phosphates,
amides, lower alkyl carboxylic acids and lower hy
droxyalkyl carboxylic acids; and from about 0.2%
‘to 6% by weight of rhodamine B base comprising
incorporating therein from about 1% to 10% by
weight of tri-iso-propanolamine.
dicyandiamides, 8-hydroxyquinolinates, nitriles, mer
captides, 'hydroxy-substituted lower alkyl and alkyl
35
19. A method of inhibiting sludge formation in a
fungicidal composition containing from about 1% to 15 %
by weight of a compound of the formula:
40
wherein
R is an ‘aliphatic radical of 1 through 6 carbons atoms
and
45
X is selected from the group ‘consisting of phosphates,
dicyandiamides, S-hydroxyquinolinates, nitriles, mer
captides, hydroxy-substituted lower alkyl and alkyl
ene mercaptans, hydroxides, lower alkyl sulfon
amides, lower alkyl carboxylic acids and lower hy
idroxyalkyl carboxylic acids; and from about 0.2%
to 6% by Weight of rhodamine B lbase, comprising
incorporating therein 1% to 6% by weight of d-i-sec
butanolamine.
References Cited in the ?le of this patent
UNITED STATES PATENTS
1,618,370
1,688,720
2,422,951
2,958,625
Engelmann __________ __ Feb. 22,
Kl'ages ______________ __ Oct. 23,
Conant _____________ __ June 24,
Rebold _______________ __ Nov. 1,
‘1927
1928
1947
1960
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