Note : Les descriptions sont présentées dans la langue officielle dans laquelle elles ont été soumises.
1(J47400
; This invention relates to surface coating
compositions which incorporate insecticides.
Although it has previously been proposed to
~ lncorporate insecticidal substances in paints and
'~ 5 simllar surface coating compositions, these proposals
have not always been satisfactory when put into
practise. Chlorinated hydrocarbon insecticides which
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- may have the required persistance are now considered
~ to be envlronmentally unacceptable. When other active
.. . .
ingredients such as organophosphorus compounds have
been used they are not sufficiently stable or persistant,
and the insecticldal effect does not persist for a long
enough period after the paint has been applied. In the
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~ Annual Report of the Danish Pest Infestation Laboratory
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~' lS for 1972 (page 19) it is reported that paints
,~j incorporating 0,0,0',0l-tetramethyl 0,0'-thiodl-~-
, phenylene phosphorothioate were ineffective in controlling
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~ mosquitos, and that those containing fenitrothion or
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dimethoate were active 6 days after application. However
, 20 to be really useful the insecticidal effect must persist
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for several weeks and preferably for several months.
We have now dlscovered that certain organophosphorus
lnsecticides are in fact very useful for incorporation
ln surface coatlng compositions, and such compositions
possess advantages over those previously proposed.
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According to the present invention a surface
coating composition comprises as an insecticidal
ingredient either pirimiphos-methyl or pirimiphos-ethyl.
Pirimiphos-methyl is the IS0 recommended common
-- 5 name for 0,0-dimethyl 0-2-diethylamino-4-methylpyrimidin-
6-yl phosphorothionate, and pirimiphos-ethyl is the IS0
recommended common name for 0,0-diethyl 0-2-diethylamino-
4-methylpyrimidin-6-yl phosphorothionate. They are also
known by the Registered Trade Marks 'Actellic' and
'Primicid' respectively.
By the term "surface coating composition" we intend
any paint, distemper, colour wash (including whitewash),
varnish or lacquer composition (but not including
- printing ink compositions) which is adapted to be applied
by brushing, rolling or spraying on to a surface to
protect or colour the surface. Such compositions may
contain any of the conventional constituents of surface
; coating compositions such as pigments, fillers, solvents,
,~ extenders, polymers (for example,alkyd resinq, epoxy
:
resins, and the like), diluents, drying oils, and the
like, as well as the insecticidal components. Where a
paint is concerned it may be an aqueous or non-aqueous
paint, such as, for example, an emulsion based paint,or a
gloss paint based upon a solvent such as white spirit.
Pirimiphos-methyl is a preferred insecticidal
agent for u~e in the surface coating compositions of
this inventlon because of its low toxicity to mammals.
Hence the surface coating compositions comprising it may
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)47400
be safely used in domestic dwellings and public
buildings, and for public health uses, for example in
kitchens, food stores and hospitals. They may be
.... .
used additionally for the treatment of farm buildinqs,
animal houses and grain silos, and for treating the
interior surfaces of the holds of ships.
In a preferred aspect of the invention the
insecticidal component is added to the composition in
a microencapsulated form, in which the capsule coat is,
-~ 10 for example, a cross linked or non-cross linked
,` polyamlde or polyurea.
The invention compositions may comprlse from 0.2%
to 7.5% by welght of the insecticidal component, and
; preferably from 0.75% to 5.0% by weight.
The invention compositions may be prepared in any
conventional manner with the insecticidal component
being added at any convenient stage during the process
of preparation.
Thus in the case of an oll based paint, a varnish
or lacquer composition the insectlcidal ingredient may
; be mixed into the otherwise completed composition. In
* such cases the lnsecticidal lngredlent may be added in
~ an undlluted form or it may be added as a solutlon ln
; a sultable solvent.
,
In the ¢ase of an emulslon based paint the
lnsectlcldal component i8 usually dlsp~rsed ln an aqueous
phase, for example an aqueous dispersion comprising say
25% or 50% w/v of the insecticidal component, and this
i~ then added to the mlll base mlxed together with the
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~3474
polymer latex dispersion, or it may be added to the
whole paint after the polymer latex has been mixed with
the mill base.
The following examples illustrate the inventlon.
ExAMæLE 1
An emulsion paint composition is prepared in the
usual way by forming a mill base by grinding together
pigment,water and a small amount of a dispersing agent
, in a colloid mill, and thereafter adding to the mill
base a polyvinylacetate/ethyl acrylate copolymer
latex dispersion in water the whole being blended in
a colloid mill. To this mixture is then added a 20%
w/v suspension of microencapsulated pirimiphos-methyl,
in which the capsules are coated with polyamide obtained
,...
from the condensation of adipoyl chloride and a mixture
of ethylene diamine and diethylenetriamine by an
interfacial process, the addition being at a rate to
~ give 5.0% w/w pirimiphos-methyl in the composition.
,~ After a further period of blending to disperse the
i 20 pirimiphos-methyl throughout the composition there is
, obtained an emulsion paint composition suitable for
,~ use on prepared plaster walls.
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- EXAMPLE 2
Pirimiphos-methyl is added to a nitrocellulose
based lacquer composition to give a concentration of
2% by weight of the insecticide in the lacquer.
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EXAMPLE 3
; Pirlmiphos-methyl is mixed with a polyurethane
based clear varnish compositlon to give a
concentratlon of 0.8% w/w of the insecticide in the
~ 5 varnish.
,~ EXAMPLE 4
i This example illustrates the pxeparation of an
, . . .
~ insecticidal emulsion paint.
, :
A 50% emulsiflable concentrate of the insecticide
was prepared by mixing together the following
constituents ln the proportions stated.
,.,
; Pirimiphos_methyl 50.0% w/v
Epichlorohydrin 2.0% w/v
"Arylan" CA 5.0% w/v
-~ 15 "Lubrol" N.13 5.0% w/v
' "Aromasol" H to 100.0% w/v
.,;: . .
"Arylan", "Lubrol" and "Aromasol" are Registered Trade
Marks. "Arylan" CA is sodium dodecylbenzenesulphonate,
... .
"Lubrol" N.B. is a condensate of nonyl phenol with
ethylene oxlde, and "Aromasol" H i8 a mixture of alkyl
benzenes.
The emulsifiable concentrate was then thoroughly
mixed with "Dulux" white matt emulsion paint ~o give
an emulsion palnt containing 3.2% w/w of pirimiphos-
methyl. "Dulux" is a Registered Trade Mark.
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EXAMPLE 5
This example illustrates the preparation of an
insecticidal emulsion paint incorporating
microencapsulated primiphos-methyl.
An aqueous suspension containing 20% w/v of
microencapsulated pirimiphos-methyl was obtained by
the interfacial condensation of a mixture of ethylene
diamine and diethylene triamine, with a mixture of
~`, 1,3- and 1,4-toluene diisocyanate in the presence of
plrimiphos methyl. This was added to "Dulux" white
matt emulsion paint at a rate which gave an emulsion
paint containing 3.2% w/w of pirimiphos-methyl.
EXAMPLE 6
An insecticidal emuslion paint was prepared as
in the previous example but prior to mixing in the
microcapsules they were separated from the medium in
; which they were prepared by centrifugation and
- dispersed in distilled water to give an emulsion paint
containing 3.2% w/w of pirimiphos-methyl.
- 20 EXAMPLE 7
- This example illustrated the preparation of an
insecticidal gloss paint. Pirimiphos-methyl(technical
grade) was added to "Dulux" white gloss paint at a
; rate whiçh gave an insecticidal gloss paint containing
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3.2% w/w of pirimiphos methyl.
EXAMPLE 8
This example compares the insecticidal
properties of various paint formulations incorporating
pirimiphos-methyl with similar formulations
incorporating fenitrothion.
The ~arious formulations used are set out as
follows:
A. Emulsion paint contalning pirimiphos-methyl
prepared by the method of Example 4.
B. Emulsion paint containing pirimiphos-methyl
prepared by the method of Example 5.
C. Gloss paint containing pirimiphos-methyl
prepared by the method of Example 7.
D. Emulsion paint containing fenitrothion prepared
by the method of Example 4 but using
fenitrothion in place of pirimiphos-methyl.
E. Gloss paint containing fenitrothion prepared
by the method of Example 7 but using
fenitrothlon (technical grade) in place of
pirimiphos-methyl.
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l~J~74(~)
F. Emulsion paint containing pirimiphos-methyl
prepared by the method of Example 6.
G. Untreated emulsion paint.
H. Untreated gloss paint.
Formulations A to E were tested at the following
dilutions of insecticidal component: 0.1%. 0.2%,
0.4%, 0.8%, 1.6% and 3.2%.
The test was conducted as follows. Single films
of all paints, irrespective of formulation, were
applied to plywood plaques (lO cm x 10 cm). Six days
after painting the plaques were bioassayed with
female organophosphorus-susceptible houseflies, using
two or three replicates for each dilution. In each
case the flies were caged over the painted surface and
the knock-down or kill of the flies assessed at
lntervals over a two hour period.
The results are set out in Table 1 below.
Assuming that the paint films were 0.001 inch
(0.0254 mm) thick then the deposits of pirimiphos-methyl
or fenitrothion from the various dilutions were as
follows:-
11)4~4UO
0.1% 26 mg/m2
0. 2% 52 mg/m2
0. 4% 104 mg/m2
0. 8% 208 mg/m2
l. 6% 416 mg/m2
3 . 2% 832 mg/m2
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Comparisons of the results obtained for
formulations A and D and also for formulations C and
E show that a superior insecticidal effect is shown
by pirimiphos-methyl in both emulsion and gloss paints,
giving a faster rate of knock down and kill of
houseflies than fenitrothion. It should also be
noted that pirimiphos-methyl is active at lower rates
of applicatlon than is fenitrothion.
EXAMP~E 9
Thls example lllustrates thé perslstance of the
insecticidal properties of palnt films incorporating
plrlmlphos-methyl. The technique used was as follows:-
Minlature rooms were prepared from plywood,
these being in the form of 12 inch (approximately
30 cm) cubes. Four l inch (2.54 cm) diameter holes
were cut in the ceilings for ventilation and before
the commencement of the tests these were covered with
fine-mesh polyester netting. The rooms were painted
with the formulation under test in one of two ways.
Either two sides and the ceillng (2SC) were palnted
wlth a slngle coat, or a slmulated mlniature door,
window frame and skirtlng board (MR).
Three formulation types were tested, an emulsion
palnt, a gloss palnt (each prepared as for the
prevlous example except that they contained 5.0% w
of plrlmlphos-methyl), and an epoxy resln palnt.
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This latter was prepared by mixing in technical
pirimiphos-methyl to the epoxy base before the
additiGn of the activator solution. In each case
a comparison was made with rooms painted with the
corresponding paint formulation without any
insecticidal ingredient (control), and each
treatment was assessed as the mean of two replicates.
Houseflies and cockroaches were introduced into
the rooms at various intervals after painting and
the mortality assessed after 24 hours, and additionally
in some cases after 2 hours. The results, which are
given in Tables 2 and 3 demonstrate that the
insecticidal effect of paints incorporating pirimiphos-
methyl persists for at least seven months.
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