CA1047400A - Surface coating compositions - Google Patents

Abstract

ABSTRACT OF THE DISCLOSURE
Surface coating compositions (e.g. paints, varnishes, lacquers) compromising as an insecticidal ingredient either pirimiphos-methyl or pirimiphos-ethyl.

Description

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 .:
- 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 , ~ Annual Report of the Danish Pest Infestation Laboratory .~ ,. . .
~' 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 : . .
~ mosquitos, and that those containing fenitrothion or :, dimethoate were active 6 days after application. However , 20 to be really useful the insecticidal effect must persist ., , 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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~047400 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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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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; 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.
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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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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.

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.

- 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.

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.

` -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 11~474UO
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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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, ~4~00 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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Claims (9)

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

1. A surface coating composition comprising from 0.2% to 7.5% by weight of pirimiphos-methyl or pirimiphos-ethyl as an insecticidal ingredient.

2. A paint composition comprising from 0.2% to 7.5%
by weight of pirimiphos-methyl as an insecticidal ingredient.

3. A composition as claimed in Claim 1 wherein the insecticidal ingredient is in a microencapsulated form.

4. A composition as claimed in Claim 3 in which the capsule coat is a cross-linked or non-cross-linked polyamide or polyurea.

5. A composition as claimed in Claims 1, 2 or 3 comprising from 0.75% to 5.0% by weight of the insecticidal ingredient.

6. An emulsion paint further comprising from 0.2 to 7.5% by weight of pirimiphos-methyl in a microencapsulated form in which the capsule coat is a non-cross linked polyamide derived from adipoyl chloride and a mixture of ethylene diamine and diethylene triamine.

7. An emulsion paint further comprising from 0.2 to 7.5%
by weight of pirimiphos-methyl in a microencapsulated form in which the capsule coat is a non-cross linked polyurea derived from toluene diisocyanate and a mixture of ethylene diamine and diethylene triamine.

8. A gloss paint further comprising from 0.2 to 7.5% by weight of pirimiphos-methyl.

9. An epoxy resin paint further comprising from 0.2 to 7.5% by weight of pirimiphos-methyl.