Process for preparing insecticidal vapours-emitting composition on a pyrethrinoid base

This invention relates to compositions intended to emit characid insecticidal vapors. contain a compound of the pyrethrinoid family and a new stabilizer.

It is well known that insecticidal substances are used for the emission of vapors for the destruction of insects within inhabited places. However, there is only one substance capable of providing at room temperature a percentage of vapor sufficient for effective insecticidal action;

AIRWICE AG.,

PREPARATION FOR A PIRETRINOI BASED COMPOSITION FOR EMISSION OF INSECTICIDATED VAPORS

-2·

<img file="PT72609B_D0001.tif" />

This substance is an organophosphate compound known by the name dichlorvos; However, it is sufficiently high in toxicity (acute oral DL 5θ close to 55 mg / kg) that other insecticidal agents are preferred instead: these preferably belong to the family of pyrethroids which are generally very toxic to man and domestic animals. However, they require a high temperature for evaporation at an effective concentration and / or a very large evaporation surface.

French Patent No. 2 322 546 to OIBA-GEIGY AG discloses a pyrethroid vapor emitting device using a temperature of 65 to 90 ° C but requiring an evapo surface. may reach several square centimeters.

In French Patent 1,384,062 and Italian Patent No. 713 459 to FUMAKILLA LTd, a pyrethroid vapor emitting device is described having a surface area of ​​only a few square centimeters but requiring a higher temperature.

This type of device is marketed worldwide and uses a temperature generally of between 150 and 160 ° C.

It is well known that at temperatures of this order pyrethroids undergo very rapid and very high decomposition; PUMAEILLA LTd cited patents contain examples of this decomposition at temperatures ranging from 100 to 160 ° C (12 to 69% decomposition within 8 hours).

An attempt has been made to remedy this by using stabilizers chosen from the various chemical classes. In several patents the use of aril is recommended.

amines such as phenylnaphthylamines. (French Order n $

226 112; U.S. Patent Nos. 3,723,615, 3,819,823 β

-5 • ν ..

<img file="PT72609B_D0002.tif" />

954 025) paraffenylene diamine derivative (Japanese Applications Nos. 7 598 025 and 7 598 024); These compos. They are particularly toxic and for this reason they are not used in practice. Substituted phenol derivatives such as tertiabutyl-2-methoxy-4 phenol (BHA) and dithertiobutyl-2,6-methyl-4 phenol (ΒΞΤ) or biphenols such as bis (tertiarybutyl-5-ethyl) are preferred. 5 hydroxy-2 phenyl) methane and bis (tertiary butyl-5-hydroxy-4 phenyl) methane (French applications 2,226,112 and 2,522,5455 Japanese applications 7,245,226 and 7,598,024 British patents 1,288,158, 1,295,039, 1,404,262, 1,427,309, 1 429 457 and 1 445 533) · Unfortunately, the action of these phenolic compounds is often insufficient to protect pyrethroids at temperatures exceeding 100 ° C and above 150 ° C.

The use of benzodioxole family compounds (Japanese application 7 399 328) has also been recommended: the use of these compounds, such as piperonylbutoxide which is the most common, has long been known, but large amounts of this compound need to be used. ; This results in a noticeable increase in cost and, on the other hand, the formation of smell when such products are put into practice.

Certain hydroxybenzyl phosphonates have now been found to achieve pyrethrinoid stabilization not only at temperatures of 150 θ to 160 ° C, but also at much higher temperatures, thus allowing the use of far less volatile pyrethrinoids than are commonly used.

Hydroxybenzyl phosphonates are known compounds described in French Patents 1 520 575 0 2 255 025 β in US Patent 5,224,973. These oils are known for their stabilizing properties to protect polymers such as rubber, polyethylene and oils and fats usable as lubricants;

However, they have never been used or recommended to prevent the degradation of molecules as different from polymers and lubricants as are the pyres, trinoids, and especially at particularly high temperatures.

<img file="PT72609B_D0003.tif" />

It is customary to use in all insecticidal devices of the aforementioned type allethrin or its resolved isomers, as these compounds have a relatively high vapor tension within the pyrethrinoid family; however, they do not always show sufficiently harmful action towards certain insects such as flies, and it is therefore interesting to be able to use other compounds alone or in combination to increase the lethal effect and / or the rate of action: but these other compounds, which require a higher temperature, are rapidly decomposed by heat.

On the other hand, the use of a stabilizer of a known type to try to stop this decomposition is generally not sufficient, probably because of its too rapid evaporation.

The present invention obviates this drawback by allowing the preparation of pyrethrinoid-based composition withstanding high and prolonged temperatures.

The invention is therefore directed to compositions for emitting insecticidal vapors by heating, comprising;

A- at least one insecticidal substance of the pyrethinoid family.

B- optionally an inert adjuvant for substance A is selected from diluents, thickeners, flavorings, synergists, dyes, repellents, solid supports and

<img file="PT72609B_D0004.tif" />

oxidising agents, said compositions comprising:

0- a stabilizer chosen from the compounds defined by the chemical formula ho-;

/

<img file="PT72609B_D0005.tif" />

R '”0 - R

R 'where R' represents one or two optional alkyl radicals containing from one to twelve carbon atoms, R 'and R', the same or different each represent an alkyl radical containing one to eighteen carbon atoms, and R * and R may together represent a divalent saturated hydrocarbon group containing two to seven carbon atoms 5 R¹ represents a hydrogen atom or an alkyl radical containing one to seven carbon atoms.

Examples of stabilizer C include the following compounds (these compounds are described in French Patents 1,320,375 θ 2,253,025 ® in US Patent 3,224,973):

0,0-dibutyl (hydroxy-4-benzyl) phosphonate (hydroxy-4-benzyl) 0,0-butanediyl-1,4 (hydroxy-4-benzyl) phosphonate 0,0-butanediyl-1,2 (hydroxy) phosphonate -4-0,0-pentanediyl-1,5 (hydroxy-4-ethyl-2-benzyl) 0.0-dibutyl (hydroxy-4 nonyl-3-phenyl) -1-butylphosphonate phosphonate of 0.0-dioctyl 0,0-dihexyl (hydroxy-4-amyl-3-phenyl) -ethyl-ethyl phosphonate 0,0-diethyl (hydroxy-4-methyl-3-isopropyl-5-benzyl) phosphonate 2- (hydroxy-4-tert-butyl-3-benzyl) phosphonate 0.0-diisopropyl 0,0-dihe-6- (hydroxy-4-methyl-3- (dodecyl-3) -4-benzyl) phosphonate

<img file="PT72609B_D0006.tif" />

0.0-dioctadecyl (hydroxy-4 methyl-3-tertiarybutyl-5-benzyl) -ptyl (hydroxy-4-diterciobutyl-5-benzyl) -phosphonate 0.0-dioctadecyl-hydroxy-4-methyl-3-tertiary-butyl-5-benzyl ) O-O-diisopropyl (hydroxy-4-dimethyl-3,5-benzyl) 0.0-dibutyl (hydroxy-4-diethyl-3,5-benzyl) phosphonate 0,0-dibutyl (hydroxy-4-dipropyl) phosphonate 3,5-benzyl) 0,0-dipropyl (hydroxy-4-diisopropyl-3,5-benzyl) phosphonate 0,0-diethyl (hydroxy-4-dibutyl-3,5-benzyl) phosphonate phosphonate 0,0-dimethyl (hydroxy-4-diisobutyl-3,5-benzyl) -0,0-dimethyl-hydroxy-4-diteroiobutyl-3,5-benzyl) -0,0-dimethyl (hydroxy-4-diterciobutyl-3,5) phosphonate O-ethyl and O-ethyl (hydroxy-4 diterciobutyl-3,5-benzyl) phosphonate 0,0-diisopropyl (hydroxy-4 diterciobutyl-3,5-benzyl) phosphonate 0,0-diisopropyl (hydroxy-4) phosphonate 0-butyl diterciobutyl-3,5-benzyl) 0-dibutyl (hydroxy-4 diterciobutyl-3,5-benzyl) phosphonate 0-methyl and 0-methyl (hydroxy-4-diterciobutyl-3,5-phosphonate) benzyl) 0,0-diisobutyl (hydroxy-4-diterciobutyl-3,5-benzyl) phosphonate 0,0-ditherciobutyl-phosphonate (hydroxy-4-diterciobutyl-3,5-benzyl) 0,0-dipentyl (hydroxy) phosphonate -4-di-dopylbutyl-3,5-benzyl) 0.0-diisopenyl (hydroxy-4-ethyl-3-isopropyl-5-phenyl) -phosphonate 0,0-di-pentyl-hydroxy-4-dodecyl-3-octyl-5-phenyl phosphonate 1-0.0didecyl (1-hydroxy-4-amyl-3- (heptyl-2) -5-phenyl) -1-propyl phosphonate

0,0-diheptyl

<img file="PT72609B_D0007.tif" />

0,0-diendecyl (hydroxy-4-diterciobutyl-3,5-benzyl) 0.0-ethanedyl-1,2 (hydroxy-4) (hydroxy-4-butyl-3-hexyl-5-phenyl) -1,2-ethyl-2-hexylphosphonate 0,0-propane diyl-1,2 (hydroxy-4-diterciobutyl-3,5-diyl-1,3 (hydroxy-4-diterciobutyl-3,5-diyl-1,2-hydroxy-diterciobutyl-3,5-benzyl) phosphonate 4-diterciobutyl-3,5-diyl-1,3 (hydroxy-4-diterciobutyl-3,5-diyl-1,5 (hydroxy-4-diterciobutyl-3,5,2,2-propanediyl-1,3 (hydroxy-4-diterciobutyl-3, 5 pentanediyl-2,4 (hydroxy-4 diterciobutyl-3,5 2,2-propanediyl-1,3) (hydroxy-4-diterciobutyl-3,5-propanediyl-1,2) (hydroxy-4-diterciobutyl-3,5) 2,2-propanediyl-1,3) (hydroxy-4-diterciobutyl-3, 5-propyl-2-propanediyl-1,3) benzyl) 0.0-propane benzyl phosphonate) 0.0-butanebenzyl phosphonate) 0.0-butanebenzyl phosphonate) 0.0-pentane benzyl) phosphonate O, O- (dimethyl.

0.0- (methyl-2 benzyl) phosphonate 0.0- (methyl-2 benzyl) phosphonate 0.0- (methyl-2 benzyl) phosphonate 0.0- (diethylbenzyl) phosphonate 0.0 - (methyl-2- (hydroxy-4-diteramyl-3,5-benzyl) phosphonate of O- (ethyl-2-methyl. 2-propanediyl-1,3).

Preferred stabilizers are (hydroxy-4-dialkyl-3,5-benzyl) phosphonates and, even better, ps (hydroxy-4-diterciobutyl-3,5-benzyl) phosphonates. Insecticidal substances A are all known to the person skilled in the art and belonging to the pyrethrinoid family without distinction of volatility. These include esters formed between a cyclopropanecarboxylic acid such as tetramethyl-2,2,3,3 cyclopropane carboxylic acid or chrysanthemic acid or

<img file="PT72609B_D0008.tif" />

(2,2-butane or 2,2-dibromo-2,2 or dichloro-2,2 or 2,2-vinyl difluoro) -3-dimethyl-2,2-cyclopropanecarboxylic acids in their racemic or resolved forms (from / or 1, cis and / or trans) and the following alcohols:

ethyl-3-methyl-2-oxo-4-cyclopentene-2-olyl-3-methyl-2-oxo-4-cyclopentene-2-olmethyl-3-methyl-2-oxo-4-cyclopentene-2-ol-crotyl-3-methyl-2-oxo-4-cyclopentene 2-ol (methyl-3-propen-2-yl) -3-methyl-2-oxo-4-cyclopentene-2-ol (chloro-2-allyl) -3-methyl-2-oxo-4-cyclopentene-2-ol (chloro-3-allyl) -3-methyl -2 oxo-4 cyelopentene-2 ​​ol furfuryl-3-methyl-2 oxo-4 cyclopentene-2 ​​ol phenyl-1 propine-2 ol (chloro-3 phenyl) -1 propine-2 ol (fluoro-3 phenyl) -1 propine-2 ol (trifluoromethyl-3-phenyl) -1 propine-2 ol (thienyl-2) -1 propin-2-ol (furyl-2) -1-propin-2-ol phenyl-4-butene-2-ol (methyl-3-phenyl) -4-butene-2-ol (methyl-2-phenyl) -4-butene-2-ol (dimethyl-2 -3 phenyl) -4 butene-2 ​​ol (methoxy-2 phenyl) -4 butene-2 ​​ol (chloro-2 phenyl) -4 butene-2 ​​ol (chloro-3 phenyl) -4 butene-2 ​​ol (dichloro-2 Phenyl) -4 butene-2 ​​ol (bromo-3 phenyl) -4 butene-2 ​​ol phenyl-4 butyne-2 ol (furyl-2) -4 butyne-2 ol (thienyl-2) -4 butyne-2 ol methyl-5 hexene-3-yno-2 ol methyl-5 hexadiene-2.5 ol dimethyl-5.6 hepten-5-yno-2 ol methyl-2 benzyl alcohol methyl-3 alcohol benzyl methyl 4-benzyl alcohol

CniS^{, rTr} dimethyl-2,3 benzyl alcohol dimethyl-2,4 benzyl alcohol dimethyl-2,5 benzyl alcohol dimethyl-2,6 benzyl alcohol dimethyl-3,4 benzyl alcohol dimethyl-3,5 benzyl alcohol trimethyl-2,4,6 alcohol benzyl alcohol allyl-4 benzyl alcohol allyl-4 dimethyl-2,6 benzyl alcohol metalyl-4 benzyl alcohol (butene-3-yl) -4 benzyl alcohol vinyl-4 benzyl alcohol cyano-4 benzyl alcohol trifluoromethyl-4 benzyl alcohol nitro-4 benzyl alcohol methyl-3 furfuryl alcohol methyl-5 furfuryl alcohol dimethyl-3,5 furfuryl alcohol dimethyl-4,5 furfuryl alcohol allyl-5 furfuryl alcohol propargyl-5 furfuryl alcohol methyl (2-furyl-3) methyl alcohol (dimethyl-2,5 furyl-3) methyl alcohol (trimethyl-2 , 4,5 furyl-3) methyl alcohol (allyl-5 furyl-3) methyl alcohol (allyl-5 methyl-2 furyl-3) methyl alcohol (methyl-2 propargyl-5 furyl-3) methyl tetrahydrophthalimidomethane1 (benzyl-5 furyl-3) methanol (alfacyanobenzyl-5 furyl-3) methanol (alfametinylbenzyl-5 furyl-3) methanol benzyl phenoxy alcohol phenoxy-3 alphacyanobenzyl alcohol phenoxy-3 alpha-methylbenzyl alcohol

These esters include, in particular, the substances known by the names alethrin, bivale trine, S-bioalethrin, cinerine, furethrin, dimethrin, benatrine.

<img file="PT72609B_D0009.tif" />

cadetrin, protrin or furamethrin, propartrin, tetramethrin, resmethrin, bioresmethrin, phenothrin, d-phenothrin, perm. trine, biopermethrin, cypermethrin, bromethrin, decamethrin and fluorethrin.

Synergistic substances, when there is at least one in the composition, are chosen from benzodioxols, polychlorinated ether oxides and N-alkyl norbornene-5 dicarboximides-2,3 ·

Suitable benzodioxols are, for example, safrol, isosafrol, cyano-5 benzodioxol-1,3, ethinyl-5 benzodioxol-1,3, dichloro-5,6 benzodioxol-1,3, cerium. ro-5 cyano-6 benzodioxol-1,3, bromo-5 cyano-6 benzodioxol-1,3, chloro-5 cyano-methyl-6 benzodioxol-1,3, chloro-5 hydroxy-6 benzodioxol-1,3 , chloro-5 hydroxymethyl-6 benzodioxol1,3, chloro-5 ethinyl-6 benzodioxol-1,3.

Suitable polychlorinated ether oxides are, for example, octachloro-1,1,1,2,6,7,7,7 oxa-4 heptane and hexachlor-1,1,2,6,7,7 oxa -4 heptadiene-1.6.

Suitable N-alkylnorbornene-5-dicarboximides-2,3 are, for example, those wherein the alkyl radical is an isobutyl, sec-butyl, terciobutyl, iso radical. pentyl, methyl-2-butyl, isohexyl, methyl-2-hexyl, ethyl-2-butyl or isodecyl.

Suitable repellants are, for example, dialkyl sueinates, maleates and fumarates, alkyl mandelates, Î ±, β-dialkylbenzamides, ocyclopropane carbonamides, alkanoyl-1-hexahydrobenzofurans and dioxa-3,6 decyl alkanoates, citronellal and its ketalkyl dialkyls and dialkylhexane.

Diluents, when there is at least one in the composition, are chosen from liquid or solid organic compounds having solvent

<img file="PT72609B_D0010.tif" />

to the insecticidal substance. The diluents used preferably have a volatility close to the volatility of subs. insecticidal substance A.

However, in order to allow the use of the compositions in certain applications, the invention does not exclude the presence of a much more volatile diluent such as dichloromethane, trichloroethane, trichlorethylene, perchlorethylene, acetone, butanone-2, methyl-4-pentane na-2, methyl, ethyl, propyl, isopropyl, butyl, amyl acetate and the other light aliphatic esters.

Low volatile diluents include those chosen from the following chemical families:

1) Monoesters formed between alkanols and monocarboxylated hydrocarbons such as alkyl acetates such as hexadecyl or octa decyl, alkyl propionates such as hexadecyl or octodecyl, alkyl butyrates and isobutyrates such as such as dodecyl, tetradecyl, hexadecyl or octa decyl, alkyl hexanoates, alkyl octanoates, alkyl decanoates, laurates, undecanoates, alkyl undecenoates and myristates such as hexyl, octyl, decyl or dodecyl, alkyl palmitates and stearates such as propyl, butyl, isobutyl, amyl, hexyl or octyl and benzoates alkyl phenylacetates and phenylpropionates such as hexyl, octyl, decyl or dodecyl.

2) Diesters formed between alkanols and dicarboxylated hydrocarbons such as, for example, dialkyl adipates such as dioctyl adipate, dinonyl adipate, didecyl sipipate and decyl adipate, dialkyl sebacates such as dibutyl sebacate, dipentyl sebacate and dioctyl sebacate,

<img file="PT72609B_D0011.tif" />

didecyl sebacate, dialkyl azelates such as dioctyl azelate and didecyl azelate, dialkyl phthalates such as dibutyl phthalate, dioctyl phthalate and didecyl phthalate, bis (undecyl) phthalate, bis (dodecyl) phthalate, bis (tridecyl) phthalate, bis (tetradecyl) phthalate and diketyl phthalate.

5) Diesters formed between unsubstituted or substituted alkyl phenols and dicarboxylated hydrocarbons such as diaryl phthalates such as diphenyl phthalate and dicresyl phthalates.

4) Diesters formed between unsubstituted or substituted cycloalkanols and dicarboxylated hydrocarbons such as dicyclohexyl phthalate, bis (trimethylcyclohexyl) phthalates and bis (tetramethyl) bis (trimethylcyclohexyl) phthalates

5) Diesters formed between phenylalkanols and dicarboxylated hydrocarbons such as dibenzyl sebacate, dibenzyl azetate and bis (phenylpropyl) sebacate

6) Diesters formed between alkanediols and monocarboxylated hydrocarbons such as trimethyl-2,2,4-pentanediol diisobutyrate 1,3

7) Triesters formed between substituted or unsubstituted alkyl phenols and phosphoric acid such as triphenyl phosphate, tris (terbuthyl-4 phenyl) phosphate and tricresyl phosphates.

8) Triesters formed between alkanols and phosphoric acid such as trioctyl phosphate, tridecyl phosphate and tricodecyl phosphate.

<img file="PT72609B_D0012.tif" />

9) Polyalkylene glycols such as polyethylene glycols and polypropylene glycols.

10) Fatty alcohols such as hexadecanol, octadecanol and octadecene-9 ol.

11) Fatty acids such as lauric, myristic, palmitic, stearic and oleic acids.

12) Alkanes containing at least 18 carbon atoms such as octadecane, eicosane, docosane and tetracosane and mixtures thereof known as petroleum jelly, paraffin oil, fatty oil, gasoline. oil, fuel oil, road oil, valve oil, mazute, vase. lina, petrolatum, gatsch, paraffin, microwax, ozokerite and ceresine,

(13) alkanones containing at least. It has carbon atoms such as caprinone, lauron, myristone, palmitone and stearone.

14) Alkenones containing at least eighteen carbon atoms such as, for example, henicosadiene-1.20 one-11 and oleone.

The thickening agents are, for example, fatty acid metal salts such as aluminum or magnesium mono-, di- and tri-stearates, or fatty acid and amine salts such as hexadecylaminopropylene amine diolates, octadecyl aminopropylene amine or octa decenylaminopropylene amine, or modified montmorillonites such as dimethyl- (heavy alkyl) -bentonite ammonium salts.

Solid supports, if there is at least one in the composition, are chosen from organic powders, mineral powders and absorbent mass materials.

<img file="PT72609B_D0013.tif" />

Organic powders can be chosen from those already known to those skilled in the art, such as starch, cereal flour, wood powder, sugars, depending on the destination of the composition.

Mineral powders can be chosen from those known to those skilled in the art, for example talc, silica, kaolin, clay, stone, slate and mineral silicates, depending on the destination of the composition. .

Absorbent putty materials may be selected from pulp and paperboard, composed of wood, cereal, alfalfa, cotton, old paper waste, asbestos, glass, wool and / or polymeric fibers and, among the listed earths, the aluminized alumina and the uncoated porcelain.

The pasta material may also contain amounts chosen from organic powders, mineral powders, pigments, dyes and binders.

The dough materials may take all known forms such as, for example, plate and block form.

The plates may be round, oval, square, rectangular, triangular or of any polygonal shape and may have a total surface area ranging from a few square centimeters to several tenths square and a thickness ranging from 0.1 to 6 milli meters.

The blocks may be prism-shaped cubic, cylindrical, elliptical, of any polyhedral shape, and their total surface may vary from

<img file="PT72609B_D0014.tif" />

-15 just a few square centimeters to several square centimeters.

Oxidizers, if there is at least one in the composition, are intended to allow their self-combustion and are chosen from those already known to those skilled in the art, such as metallic, ammonium or ammonium nitrates. nitrocellulose.

The composition preferably contains at least 5% by weight of insecticidal substance A.

The composition preferably contains from 5 to 100 parts by weight of stabilizer 0 per 100 parts of insecticidal substance A; this ratio will be advantageously between 10 and 5 parts of stabilizer 0.

When the composition does not include a solid support it is prepared by simply mixing the cold or hot constituents.

When the composition includes a solid support, such as an absorbent mass material, it is prepared by impregnating this material with the liquid mixture of the other constituents of the composition. The impregnation may be carried out by pouring the liquid mixture onto the support or by dipping the composition into the liquid, this operation being eventually followed by centrifugation; operation may be mechanized using, for example, a metering pump or a constant flow asperpipe; a pressure-adjustable roller centrifuge may also be employed to retain the liquid in the desired ratio; An adjustable speed centrifuge may also be used for the same purposes. An interesting mode of impregnation from the industrial point of view is, for example, the use of large length bands, impregnated in blocks and then cut to the desired dimensions. Impregnation may further be effected by placing the solid support under vacuum in the presence of

<img file="PT72609B_D0015.tif" />

of the liquid mixture.

The impregnation may also be carried out automatically by means of a machine comprising one or two injection syringes and a conveyor belt making the solid supports to be impregnated under said syringes. A solution of the liquid mixture may also be used in a volatile solvent as mentioned above which may then be evaporated.

When the composition comprises a solid support such as a powder and a oxidizer to obtain a self-combustible product, it is prepared by mixing the constituents with water or a volatile solvent to give a paste which has It is extruded molded or shaped and then subjected to drying according to a method known to those skilled in the art, such as placement in a hot air oven or a vacuum cabinet.

Interest of the compositions according to the present invention is illustrated by the following experiments.

Experiment 1: The following compositions 1-A and 1-B are used by impregnating 34x21x3 mm cellulose plates with the liquid mixture of the other constituents.

<td></td><td>1a</td><td>1b</td>

<td>Bioresmethrin</td><td>50 mg</td><td>50 mg</td>

<td>Stabilizer</td><td> -</td><td>20 mg</td>

<td>Dye (b)</td><td>1 mg</td><td>1 mg</td>

<td>Cellulose</td><td>880 mg</td><td>880 mg</td>

<img file="PT72609B_D0016.tif" />

-17 (a) 0.0-die (hydroxy-4-ditherciobutyl-3,5-benzyl) phosphonate. Tilo.

(b) JN organol blue

The plates thus impregnated were each placed over the appropriate part of a commercial device designed for this use and comprising a 6800 ohm heat resistance placed in a ceramic block having a heated upper surface of 35 x 20 mm.

The devices, containing the plates, were each placed in an apparatus capable of collecting all the vapors emitted during the operation, being fed by an alternating current of 220 volts for 3 hours and the heated surface temperature of 162 ° C. ° C.

After this period, the amounts of non-decomposed bioresmethrin present on the one hand on the plates and on the other on the collected vapors were measured by analysis.

The results are summarized in the table below:

<td></td><td>1a</td><td>1b</td>

<td>Quantity present on plate</td><td>17 »5 ms</td><td>48.0 mg</td>

<td>Quantity present in vapors</td><td>.at,</td><td></td>

<td>Total amount not decomposed</td><td>19.0 mg</td><td>49.5 mg</td>

<td>Quantity decomposed</td><td>31.0 mg (62%)</td><td>0.5 mg (1 %)</td>

<img file="PT72609B_D0017.tif" />

Experiment 2: This was done as in Experiment 1 using the same device and the following compositions 2-A and 2-B.

<td></td><td>2a</td><td>2b</td>

<td>d-phenothrin</td><td>50 mg</td><td>50 mg</td>

<td>Stabilizer</td><td> -</td><td>10 mg</td>

<td>Cellulose</td><td>880 mg</td><td>880 mg</td>

The device was connected to a 250-volt AC power supply allowing it to reach a temperature of 197 ° C.

The non-decomposed amounts of d-phenothrin observed after 3 hours of operation allowed the following table to be established:

<td></td><td>2a</td><td>2b</td>

<td>Quantity present on plate</td><td>5.0 mg</td><td>27.5 mg</td>

<td>Quantity present in vapors</td><td>15.0 mg</td><td>1% .5, „S &amp;</td>

<td>Total amount not decomposed</td><td>20.0 mg</td><td>47.0 mg</td>

<td>Quantity decomposed</td><td>30.0 mg (60%)</td><td>3.0 mg (6%)</td>

Experiment 3? proceeded as in experiment 1 using the same device and the following compositions 3-A and 3-B:

<img file="PT72609B_D0018.tif" />

<td></td><td>3a</td><td>3b</td>

<td>Tetramethrin</td><td>50 mg</td><td>50 mg</td>

<td>Stabilizer</td><td> -</td><td>20 mg</td>

<td>Cellulose</td><td>880 mg</td><td>880 mg</td>

The device was connected to a 250-volt AC power source allowing it to reach a tempe. 197 ° 0 ·

The amounts of non-decomposed tetramethrin observed after 3 operating hours allowed the following table to be established:

<td></td><td>3a</td><td>3b</td>

<td>Quantity present on plate</td><td>12.0 mg</td><td>25.0 mg</td>

<td>Quantity present in vapors</td><td></td><td>20.0 mg</td>

<td>Total amount not decomposed</td><td>20.5 mg</td><td>45.0 mg</td>

<td>Quantity decomposed</td><td>29.5 mg (59%)</td><td>5.0 mg (10%)</td>

Experiment 4: As in Experiment 1, using the same device and the following compositions 4-A and 4-B

<img file="PT72609B_D0019.tif" />

<td></td><td>4a</td><td>4b</td>

<td>Bioalethrin</td><td>50 mg</td><td>50 mg</td>

<td>Stabilizer</td><td> -</td><td>10 mg</td>

<td>Synergistic substance (c)</td><td>250 mg</td><td>250 mg</td>

<td>Dioctyl Sebacate</td><td>250 mg</td><td>250 mg</td>

<td>Dye (b)</td><td> -</td><td>7 mg</td>

<td>Cellulose</td><td>880 mg</td><td>880 mg</td>

(c) octachloro-1,1,1,6,7,7,7 oxa-7 heptane The device was connected to a 220 volt alternating current source to a temperature of 162 ° G.

The amounts of decomposed bioalethrin observed after 3 hours of operation allowed the following table to be established:

<td></td><td>4a</td><td>4b</td>

<td>Quantity present on plate</td><td>32 mg</td><td>47 mg</td>

<td>Quantity present in vapors</td><td>4 mg</td><td>. 5 mg</td>

<td>Total amount not decomposed</td><td>36 mg</td><td>50 mg</td>

<td>Quantity decomposed</td><td>14 mg (28%)</td><td>0 mg (0%)</td>

Experiment 5: As in Experiment 1, using the same device and the following composition 5-A:

<img file="PT72609B_D0020.tif" />

<td>S-bioalethrin</td><td>90 mg</td>

<td>Stabilizer</td><td>10 mg</td>

<td>Butyl Stearate</td><td>90 mg</td>

<td>Cellulose</td><td>414 mg (d)</td>

(d) plate thickness: 1.5 n one device was fed with AC to maintain a temperature of 162 ° C for 8 hours, at which time the evaporated and remaining S-bioalethrin amounts were measured by analysis ; The results were as follows:

Amount

Amount

Amount

Quantity present on plate present in total decomposed vapors decomposed

9.6 mg 78.7.mg

88.3 mg

1.7 mg (1.9%)

Experiment 6: as in experiment 1, using the following composition 6-A obtained by impregnating 2 cm surface and 1.25 mm round cellulose plates:

&lt;'ί &lt;

S-bioalethrin Stabilizing Cellulose mg 1.25 mg

125 The device was fed with alternating current to maintain a temperature of 162 ° C for 6 hours, at which time the evaporated and remaining amounts of S-bioalethrin were measured by analysis; The results were as follows:

<img file="PT72609B_D0021.tif" />

-22Quantity present on plate Quantity present on vapors Total amount not decomposed Quantity decomposed mg 18.6 mg

18.6 mg 1.4 mg (7%)

Experiment 7? This was done as in experiment 1 using a device having a heated top surface of 36 x 40 mm and comprising two 6800 ohm heating resistors each placed in a ceramic block β connected in parallel to an alternating current source. 193 volts of method to heat the surface to a temperature of 160 ° C.

The following plates 7-A to 7-D have been used successively with the dimensions of 35 x 30 x 1.5 mm:

<td></td><td>7a</td><td>7b</td><td> 7-0</td><td>7-D</td>

<td>d- phenothrin</td><td>40 mg</td><td>50 mg</td><td>50 mg</td><td>40 mg</td>

<td>stabilizer</td><td>10 mg</td><td>10 mg</td><td>5 mg</td><td>2 mg</td>

<td>cellulose</td><td>630 mg</td><td>630 mg</td><td>630 mg</td><td>630 mg</td>

The plates were then placed successively on the heated part of the device for 8 hours at the end of which the amounts of d-phenothrin evaporated and the remainder were measured by analysis; The results were as follows:

<img file="PT72609B_D0022.tif" />

<td></td><td>7a</td><td>7b</td><td>7c</td><td>7-D</td>

<td>Quantity present on plate</td><td>25.0mg</td><td>30.0mg</td><td>28.0mg</td><td>17.0mg</td>

<td>Quantity present in vapcres</td><td>14.3mg</td><td>16.7mg</td><td>18.2mg</td><td>15.9mg</td>

<td>Total amount not decomposed</td><td>39.3mg</td><td>46.7mg</td><td>46.2mg</td><td>32.9mg</td>

<td>Quantity decomposed</td><td>0.7mg (1.8%)</td><td>3.3mg (6.6%)</td><td>3.8mg (7.6%)</td><td>7, 1mg (17.8%)</td>

Experiment 8: As in experiment 1, the same device and the following compositions 8-A and 8-B were used:

<td></td><td>8a</td><td>8b</td>

<td>Permethrin</td><td>50 mg</td><td>50 mg</td>

<td>Stabilizer</td><td> - '</td><td>15 mg</td>

<td>Cellulose</td><td>880 mg</td><td>880 mg</td>

The device was connected to an alternating current source to give a temperature of 260 ° C on the heated surface and the amount of permethrin evaporated and the remainder was measured by analysis after three hours of operation; The results were as follows:

<td></td><td>8a</td><td>8b</td>

<td>Quantity present on plate</td><td>12.6 mg</td><td>17.6 mg</td>

<td>Quantity present in vapors</td><td>26.1 mg</td><td>5 ° w;</td>

<td>Total amount not decomposed</td><td>38.7 mg</td><td>48.0 mg</td>

<td>Quantity decomposed</td><td>11.3 mg (22.6%)</td><td>2.0 mg (4%)</td>

<img file="PT72609B_D0023.tif" />

Experiment 9: As in Experiment 1, using the same device and the following compositions 9-A, 9-B θ 9-0:

<td></td><td>9a</td><td>9b</td><td> 9-0</td>

<td>Decamethrin</td><td>5θ mg</td><td>50 mg</td><td>50 mg</td>

<td>Stabilizer</td><td> -</td><td>10 mg</td><td>20 mg</td>

<td>Cellulose</td><td>880 mg</td><td>880 mg</td><td>880 mg</td>

The device was connected to an alternating current source to give a temperature of 260 ° C on the heated surface and the evaporated and remaining amounts of decamine were measured by analysis after three hours of operation; The results were as follows:

Quantity present on plate Quantity present on vapors Total quantity not decomposed Quantity decomposed

<td>9a</td><td>9b</td><td> 9-0</td>

<td>30 mg</td><td>40 mg</td><td>41 mg</td>

<td>4 mg</td><td>6.5 mg</td><td>7 mg</td>

<td>34 mg</td><td>46.5 mg</td><td>48 mg</td>

<td>16 mg</td><td>3.5 mg</td><td>2 mg</td>

<td> (32 %)</td><td> (7 %)</td><td> (4 %)</td>

Experiment 10: As in Experiment 1 using a device having a heated top surface of 36 x 40 mm and comprising two 6800 ohm heating resistors each placed in a ceramic block and connected in parallel to an alternating current source. 193 volts to heat the surface to a temperature of 160 ° C.

Subsequently, the following 10-A to 10-E sinks having the dimensions of x 40 x 2.6 mm were used.

rrat

<img file="PT72609B_D0024.tif" />

<td></td><td>10a</td><td>10b</td><td> 10-0</td><td>10-D</td><td>10e</td>

<td>Bioresmethrin</td><td>50.0 mg</td><td>50.0 mg</td><td>50.0 mg</td><td>50.0 mg</td><td>50.0 mg</td>

<td>Stabilizer</td><td> -</td><td>4.0 mg</td><td>2.5 mg</td><td>5.0 mg</td><td> -</td>

<td>BHA (d)</td><td> -</td><td> -</td><td> -</td><td> -</td><td>2.5mg</td>

<td>BHT (d¹)</td><td>2.5 mg</td><td> -</td><td> -</td><td> -</td><td> -</td>

<td>Cellulose</td><td>1680 mg</td><td>1680 mg</td><td>1680 mg</td><td>1680 mg</td><td>1680 mg</td>

<td>active OH</td><td> 11,3</td><td> 11,2</td><td> 7,0</td><td> 14,0</td><td> 13,9</td>

(d) Terciobutyl-2 methoxy-4 phenol (d ') Diterciobutyl-2,6 methyl-4 phenol

The plates were then placed successively on the heated portion of the device for 3 hours at the end of which the evaporated and remaining amounts of bioresmethrin were measured by analysis; The results were as follows:

<img file="PT72609B_D0025.tif" />

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<td></td><td>E4</td><td>W</td><td>why</td><td>why</td><td>O</td><td>The</td>

(e) Bis (d.iterciobutyl-3,5-hydroxy-4-phenyl) methane - (e ') Bis (tertiarybutyl-g-hydroxy-2-methylphenyl)

<td colspan="2"></td><td colspan="3">m</td>

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<td></td><td></td><td>frog</td><td>frog</td><td>frog</td>

<td>frog</td><td></td><td>P</td><td>xl</td><td>O</td>

<td>-P</td><td></td><td>d</td><td>right</td><td></td>

<td>d</td><td></td><td>frog</td><td>xi</td><td>rf</td>

<td>frog</td><td></td><td>rf</td><td>• rl</td><td>right</td>

<td>d</td><td></td><td>right</td><td>P</td><td>d</td>

<td>d</td><td></td><td>í&gt;</td><td>d</td><td>O</td>

<td>O</td><td></td><td>• rl</td><td> 3</td><td>P</td>

<td>O</td><td></td><td>m</td><td>d,</td><td></td>

<td></td><td></td><td>frog</td><td>σ¹</td><td>frog</td>

<td>frog</td><td></td><td>frog</td><td></td><td>O</td>

<td>xl</td><td></td><td>O</td><td>frog</td><td>x)</td>

<td></td><td></td><td>d</td><td>right</td><td>right</td>

<td>frog</td><td></td><td>frog</td><td></td><td>P</td>

<td>-P</td><td></td><td rowspan="2">right</td><td>frog</td><td>r4</td>

<td>d</td><td></td><td>• rl</td><td>d</td>

<td>O</td><td></td><td>rf</td><td>Ctí</td><td>frog</td>

<td>P</td><td></td><td> 3</td><td>The</td><td>frog</td>

<td></td><td></td><td></td><td>right</td><td rowspan="2">d</td>

<td>Ctí</td><td></td><td>right</td><td></td>

<td>rf</td><td></td><td>x)</td><td>frog</td><td>frog</td>

<td> 3</td><td></td><td>right</td><td>cri</td><td>O</td>

<td></td><td> •</td><td>O</td><td>xi</td><td></td>

<td>right</td><td>O</td><td>frog</td><td> 1-4</td><td>frog</td>

<td>O</td><td>O</td><td> 3</td><td>right</td><td>frog</td>

<td>rl</td><td>ç-</td><td>Tti</td><td>d</td><td>• rl</td>

<td>right</td><td>&lt;c</td><td>right</td><td>• rl</td><td>r — 1</td>

<td>faO</td><td></td><td>O</td><td>P</td><td>KCtí</td>

<td>• rl</td><td></td><td>O</td><td></td><td>d</td>

<td>rd</td><td>&lt;D</td><td> 1—1</td><td>O</td><td> 3</td>

<td></td><td>xí</td><td>O</td><td>d</td><td></td>

<td>• rl</td><td></td><td>O</td><td></td><td>d</td>

<td>O</td><td rowspan="2">right C_1</td><td></td><td> *·</td><td>O</td>

<td>P</td><td></td><td rowspan="2">frog right d</td><td>Federal Police</td>

<td>O</td><td> £</td><td>d</td><td>m</td>

<td></td><td>P</td><td>O</td><td>O</td><td>right</td>

<td>• rl</td><td>right</td><td>«D</td><td>jd</td><td>x)</td>

<td>P</td><td>d</td><td></td><td></td><td>• rl</td>

<td>• rl</td><td>frog</td><td>frog</td><td>rc</td><td>xi</td>

<td>frog</td><td>Pi</td><td>right</td><td></td><td>frog</td>

<td>O</td><td>d</td><td>O</td><td>frog</td><td rowspan="2">The</td>

<td>Federal Police</td><td>frog</td><td>right</td><td>P</td>

<td>frog</td><td>-P</td><td>I — 1</td><td>d</td><td>rf</td>

<td>• rl</td><td rowspan="2">right</td><td rowspan="2">P</td><td> 3</td><td> 3</td>

<td>x)</td><td>d</td><td>d</td>

<td></td><td>laugh</td><td>frog</td><td>d</td><td>O</td>

<td>O</td><td> 3</td><td></td><td>xi</td><td>P</td>

<img file="PT72609B_D0026.tif" />

<img file="PT72609B_D0027.tif" />

<td></td><td>bD</td><td>hd</td><td>good</td><td>bD</td><td></td>

<td rowspan="2"></td><td>d</td><td>The</td><td>The</td><td>The</td><td rowspan="2">ΐΜ</td>

<td>O</td><td>O</td><td>O</td><td>O</td>

<td> 1</td><td> ·*</td><td> »</td><td>r »</td><td>r »</td><td>co</td>

<td>H</td><td>O</td><td>i — 1</td><td>rH</td><td>σ '</td><td>IC</td>

<td>H</td><td>CJ</td><td>r4</td><td>rc</td><td>rH</td><td></td>

<td></td><td>bd</td><td>bd</td><td>bd</td><td>bfl</td><td></td>

<td></td><td>The</td><td>The</td><td>The</td><td>The</td><td rowspan="2"></td>

<td>O</td><td>σ »</td><td>vD</td><td>IC</td><td>LC</td>

<td> 1</td><td> ·*</td><td> »</td><td> 9*</td><td> ♦»</td><td> [&gt;-</td>

<td>H</td><td>σ '</td><td>H</td><td>H</td><td>oo</td><td>rH</td>

<td>r4</td><td>CJ</td><td>r — i</td><td> •3·</td><td></td><td>Z</td>

<td></td><td>bD</td><td>bd</td><td>good</td><td>bD</td><td></td>

<td></td><td>The</td><td>The</td><td>The</td><td>The</td><td rowspan="2"></td>

<td>O</td><td>O</td><td>tc</td><td>IC</td><td>LC</td>

<td> |</td><td>r *</td><td> «</td><td>r »</td><td> «*</td><td>r_ |</td>

<td>H</td><td>Cb</td><td>O</td><td>cc</td><td>O</td><td>Cl</td>

<td>H</td><td>CJ</td><td>H</td><td>IC</td><td>r4</td><td>s_z</td>

<td></td><td></td><td></td><td></td><td></td><td></td>

<td></td><td>bD</td><td>ω</td><td>bD</td><td> 60</td><td></td>

<td></td><td>The</td><td>The</td><td>The</td><td>The</td><td rowspan="2">ω</td>

<td>why</td><td>LC</td><td>CJ</td><td>O-</td><td>tc</td>

<td> 1</td><td>r »</td><td> 9</td><td> 9\</td><td>V »</td><td> 00</td>

<td>rd</td><td>cc</td><td>H</td><td>O</td><td>cc</td><td>rH</td>

<td>H</td><td>CJ</td><td>rH</td><td> 3·</td><td></td><td></td>

<td></td><td>bD</td><td>bd</td><td>bD</td><td>bD</td><td></td>

<td></td><td>The</td><td>The</td><td>The</td><td>The</td><td rowspan="2">r \</td>

<td> &lt;4</td><td>O</td><td>IC</td><td>LC</td><td>LC</td>

<td> 1</td><td> ·*</td><td> «</td><td> »*</td><td>r *</td><td>rc</td>

<td>r- |</td><td>LC</td><td> 00</td><td>rc</td><td>10</td><td>rc</td>

<td>fH</td><td>CJ</td><td></td><td>tC</td><td>H</td><td>O</td>

<td></td><td></td><td>frog</td><td>right</td><td></td><td></td>

<td></td><td></td><td>frog</td><td>P</td><td></td><td></td>

<td></td><td></td><td>d</td><td>frog</td><td></td><td></td>

<td></td><td>cri</td><td>O</td><td>O</td><td></td><td></td>

<td></td><td>ϋ</td><td colspan="2"></td><td></td><td></td>

<td></td><td>right</td><td>right</td><td>The</td><td></td><td></td>

<td></td><td>r ~ 1</td><td></td><td>O</td><td></td><td></td>

<td></td><td>Pi</td><td></td><td>O</td><td></td><td></td>

<td></td><td></td><td>frog</td><td>frog</td><td></td><td></td>

<td></td><td>CD</td><td>O</td><td></td><td></td><td></td>

<td></td><td>d</td><td>d</td><td></td><td>cri</td><td></td>

<td></td><td></td><td></td><td>O</td><td>P</td><td></td>

<td></td><td>frog</td><td>frog</td><td>ictí</td><td>frog</td><td></td>

<td></td><td>P</td><td>P</td><td>d</td><td>O</td><td></td>

<td></td><td>d</td><td>d</td><td></td><td> &amp;</td><td></td>

<td></td><td>frog</td><td>frog</td><td>rH</td><td>The</td><td></td>

<td></td><td>frog</td><td>w</td><td>cri</td><td>O</td><td></td>

<td></td><td>frog</td><td>frog</td><td>P</td><td>O</td><td></td>

<td></td><td>d</td><td>d</td><td>O</td><td>frog</td><td></td>

<td></td><td>Federal Police</td><td colspan="2">Pf P</td><td>X)</td><td></td>

<td></td><td>frog</td><td>frog</td><td>frog</td><td>frog</td><td></td>

<td></td><td>xi</td><td>xl</td><td>xi</td><td>xi</td><td></td>

<td></td><td>CD</td><td>right</td><td>right</td><td>CD</td><td></td>

<td></td><td>xi</td><td>xJ</td><td>d</td><td>xi</td><td></td>

<td></td><td>• rJ</td><td>♦ rl</td><td>• rl</td><td>• rl</td><td></td>

<td></td><td>-s</td><td></td><td></td><td></td><td></td>

<td></td><td> 3 2</td><td> 3 3</td><td>3 d</td><td>3 d</td><td></td>

<td></td><td>G?</td><td colspan="2">G? G?</td><td>G?</td><td></td>

<img file="PT72609B_D0028.tif" />

The results of experiments 10 and 11 show that the compositions according to the present invention provide a better stability and, therefore, a better yield of the insecticidal substance, using a stabilizer recommended by the invention rather than a stabilizer chosen from among the same ones. already known to those skilled in the art.

Experiment 12: according to experiment 1 using the same device and the following composition 12-A d-phenothrin 5 mg piperonylbutoxide 250 mg cellulose 880 mg device was connected to a 250 volt alternating current source allowing reach a temperature of 197 ° 0 ·

Evaporated and remaining amounts of d-phenothrin were measured by analysis after three hours of operation; The results were as follows:

Quantity present on plate Quantity present on vapors Total quantity not decomposed Quantity decomposed

40.0 mg

42.5 S 7.5 mg (15%)

These results should be compared to those obtained in experiments 2 and 7. They show that the compositions according to the present invention are more stable than those obtained by employing a compound of the benzodioxole family, even when used with a content of 500% ·

<img file="PT72609B_D0029.tif" />

-29cclaims