IE83720B1 - Antiparasitic composition for the treatment and protection of pets - Google Patents

Abstract

Abstracts” and of the documents quoted therein. Although this is not preferred, the composition can possibly include water, particularly at the rate ofO to 30% (volume per volume V:V), in particular from O to 5%. The composition can also include an antioxidising agent designed to inhibit oxidation of the air, this agent being in particular present at the rate of 0.005 to 1% (weightzvolume), and preferably from 0.01 to 0.05%.

Description

PATENTS ACT, 1992 960689 ANTIPARASITIC COMPOSITION FOR TI IE TREATMENT AND PROTECTION OF PETS MERIAL Anti—parasite composition for the treatment and protection of pets This invention concerns a composition for the treatment and protection of animals infested or likely to be infested with parasites.

In particular, the purpose of the invention is to control and eliminate parasites which infest pets, especially cats and dogs.

Pets are often infested with one or more of the following parasites: - cat and dog fleas (Ctenocephalides felis, Ctenocephasides sp. and others); - ticks (Rhipicephalus sp., Ixodes sp., Dermacentor sp., Amblyomma sp. and others); — gall—midges (Demodex sp., Sarcoptes sp., Otodectes sp. and others).

Fleas cause the animal profound stress and are detrimental to its health. Further, fleas are also carriers of pathogenic agents such as tape worms in dogs (Dipylidium cams), and can also attack human beings.

In the same way, ticks can also cause the animal stress and harm its health. They can also be detrimental to human beings. The most serious problem with ticks, however, is that they are carriers of pathogenic agents which can affect animals as much as human beings. Among the major illnesses which have to be prevented can be quoted Borelliosis (Borellia burgdorferi Lyme disease) and Babesiosis (or Babesia sp. pyroplasmosis), Rickettsiosis (designated by the English name of Rocky Mountain Spotted Fever). Ticks can also release toxins with paralysing and inflammatory, and sometimes fatal, properties.

Finally, the gall-midge is particularly difficult to combat because there are very few active materials in existence which act on these parasites and they require frequent treatment.

There are many insecticides in existence which are more or less active and more or less costly. However, phenomena of resistance are often connected with using them, as is the case for instance with carbamates, organo-phosphorus and pyrethroids.

Furthermore, the applications for an international patent WO—A-87 03781 and European patents EP—A—O 295 117 and EP—A—O 500 209 describe a large family of N. plienyl pyrozoles which has a Very wide spectrum of activity, including antiparasite activities.

The application for international patent W0-A-96 16544 reveals emulsionable insecticide compositions in which the active material is also a compound 1—phenyl pyrazole.

The purpose of the invention is to provide new antiparasite compositions for treating and protecting animals, compositions which are extremely effective while being easy to use.

Another purpose of the invention is to provide such compositions which are easy to use on any type of pet, whatever its size and the nature of its coat.

Yet another purpose of the invention is to provide such effective compositions which do not require spraying of the animal’s whole body.

Yet another purpose of the invention is to provide such compositions which, applied locally, will then spread over the animal’s whole body, and then dry, while avoiding as much as possible any crystallisation phenomenon.

Yet another purpose of the invention is to provide such compositions which, after drying, do not affect the appearance of the coat and, in particular, do not leave any crystals and do not make the coat sticky.

These objectives are achieved by the invention, the subject of which is antiparasite compositions for use in the treatment and protection of pets infested or likely to be infested with parasites, including the following in the form of a ready—to-use solution: a) an active insecticide material with formula (I), in which: R1 is an atom of halogen, CN or methyl; R2 is S(O)uR3 or 4,5—dicyano-imidazole 2—y1 or haloalkyl; R3 is alkyl or haloalkyl, for example lower haloalkyl; R4 represents an atom of hydrogen or halogen; or a radical NR5R6, S(O)mR7, C(O)R7, or C(O)OR7, alkyl, haloalkyl or OR; or a —N °’C(R9)(R,0) radical; R5 and R6 represent independently the atom of hydrogen or an alkyl, haloalkyl, C(O)alkyl, S(O),CF3, acyl or alcoxy-carbonyl radical; or R5 and R5 can together form a divalent alkylene radical which can be interrupted by one or two divalent hetero-atoms such as oxygen or sulphur; R7 represents an alkyl or haloalkyl radical; R8 represents an alkyl, haloalkyl radical, or a hydrogen atom; R9 represents an alkyl radical or a hydrogen atom; R0 represents a phenyl or hetero—aryl group; possibly substituted by one or more halogen atoms or groups such as OH, -O—alkyl, -S-alkyl, cyano, or alkyl; Y represents a halogen atom, a haloalkyl or haloalcoxy radical, for example lower haloalcoxy, SF5, with the possibility that: — Y is CN or NO, at positions 2 and 6 (with reference to the carbon connected to the pyrazole core and marked l); - the carbon at 2 of the phenyl radical is replaced by N; ~ Y is S(O)qCF3 in position 4, but preferably halolalkyl, haloalcoxy or SF,; in, n, q, r represent, independently of each other, a whole number equal to 0, 1 or 2; p is a whole number equal to l, 2, 3, 4 or 5, preferably equal to l, 2, or 3, particularly 3; with the reservation that, when R, is methyl, then R, is haloalkyl, R4 is NH2, p is 2, Y in position 6 is Cl, Y in position 4 is C17,, and the carbon in position 2 of the phenyl is replaced by N; or else R2 is 4,5 dicyano imidazole 2-yl, R4 is CI, p is 3, ;Y in position 6 is Cl, Y in position 4 is CF,, and the carbon in position 2 of the phenyl is replaced by =C-Cl; this compound in formula (I) being able with advantage to be present in the formulation at the rate of l to 20%, preferably from 5 to 15% (percentage by weight to volume = W/V). b) a crystallisation inhibitor, particularly present at the rate of l to 20% (W/V), preferably from 5 to 15%, this inhibitor passing the test whereby: 0.3 ml of a solution A comprising 10% (W/V) of the compound in formula (I) in the solvent defined under c) below, as well as 10% of this inhibitor, are deposited on a glass plate at 20°C for 24 hours, following which a few crystals or no crystals at all can be observed with the naked eye, in particular fewer than 10 crystals and preferably no crystals, on the glass plate;. c) an organic solvent with a dielectric constant between 10 and 35, preferably between 20 and 30, the content of this solvent c) in the overall composition preferably representing the topping up of the composition to 100%; d) an organic cosolvent with a boiling point below 100°C, preferably below 80°C and with a dielectric constant between 10 and 40, preferably between 20 and 30; this cosolvent can advantageously be present in the composition at a weightweight (W/W) ratio of d):c) between :15 and 1:2. The solvent is volatile so that it acts particularly as a drying promoter and is miscible with Water and/or solvent c); The active insecticide material preferably complies with the formula (II): in Which: Rlis an atom of halogen, CN or methyl; Rzis S(O)nR3 or 4,5—dicyano—imidazole 2—yl or haloalkyl; R3 is alkyl or haloalkyl; R4 represents an atom of hydrogen or of halogen; or a radical NR5R6, S(O)mR7, C(O)R7; or C(O)OR7, alkyl, haloalkyl or ORB or a -N=C(R9)(Rm) radical; R5 and R6 represent independently the hydrogen atom or an alkyl, haloalkyl, C(O)all S(O),CF3 or all<:oxy—carbonyl radical; or R5 and R6 can together form a divalent allcylene radical such as oxygen or sulphur; R7 represents an alkyl or haloalkyl radical; R8 represents an alkyl, haloalkyl radical or a hydrogen atom; R9 represents an alkyl radical or a hydrogen atom; R10 represents a phenyl or hetero—aryl group, possibly substituted by one or more halogen atoms or groups such as OH, —O—alkyl; —S—alkyl, cyano, or alkyl; R1, and R12 represent independently of each other a hydrogen or halogen atom and possibly CN of N02, but hydrogen or halogen is preferable; R1, represents a halogen atom or a haloallcyl, haloalkoxy, S(O)qCF3 or SF5 group; m, n, q, r represent, independently of each other, a Whole number equal to O, l or 2; X represents a trivalent nitrogen atom or a C-R12 radical, the other three valencies of the carbon atom forming part of the aromatic cycle; with the reservation that when R, is methyl, then R3 is haloalkyl, R4 is NH2, R1, is Cl, R13 is CF 3 and X is N; or else R2 is 4,5 dicyano—imidazole 2—yl, R4 is Cl, R” is Cl, R” is C173, and X is =C— C].

The alkyl radicals in the definition of the compounds in formulae (I) and (II) generally include from 1 to 5 carbon atoms. The cycle formed by the divalent alkylene radical representing R5 and R6 as well as the nitrogen atom to which R5 and R6 are connected, is generally a cycle with 5, 6 or 7 chains.

Preferably again, R, is CN, R3 is haloalkyl, R4 is NH2, R” and R12 are independently of each other a halogen atom, R1, is a haloalkyl. Preferably also, X is C-R12.

A compound (A) of formula (I) very particularly preferred in the invention is the l—[2,6— —CF3 phenyl] 3-CN 4-[SO-SF3] 5-NI-I2 pyrazole, the common name for which is fipronil.

The formula (I) compounds can be prepared using either of the methods described in patent applications WO—A-87/3 781, 93/6089, 94/21606 or the European patent application EP—A- 295 117, or any other method within the expertise of a man in the trade specialising in chemical synthesis. A man in the trade is considered, for chemically making the products covered by the invention, as having at his disposal, inler alia, the full contents of the “Chemical Abstracts” and of the documents quoted therein.

Although this is not preferred, the composition can possibly include water, particularly at the rate ofO to 30% (volume per volume V:V), in particular from O to 5%.

The composition can also include an antioxidising agent designed to inhibit oxidation of the air, this agent being in particular present at the rate of 0.005 to 1% (weightzvolume), and preferably from 0.01 to 0.05%.

The compositions according to the invention, intended for pets, especially dogs and cats, are generally applied by depositing on the skin (in English spot on or pour on); it is generally a question of localised application on a surface area of less than 10 sq. cm., especially between 5 and 10 sq. cm,, in particular at two points and preferably located between the animal’s shoulders.

After being put on, the composition spreads, particularly over the animal’s whole body, and then dries, without crystallisation and without changing the appearance (in particular there is no whitish deposit and no dusty look), or affecting the animal’s coat.

The compositions according to the invention are particularly advantageous due to their efficiency and fast action, as well as the pleasant appearance of the animal’s coat after application and drying.

As the organic solvent c) which can be used in the invention, the following in particular can be quoted: acetone, acetonitrile, benzylic alcohol, butyl diglycol, dimethyl acetamide, dimethyl formamide, n-butyl ether of dipropylene glycol, ethanol,’isopropanol, methanol, ethylene glycol rnonoethyl ether, ethylene glycol monomethyl ether, monomethyl acetarnide, monomethyl ether of dipropylene glycol, liquid polyoxy—ethylene glycols, propylene glycol, 2—pyrrolidone, particularly N-methyl pyrrolidone, diethylene glycol rnonoethyl ether, ethylene glycol, diethyl phthalate, or a mixture of at least two of them.

The solvents c) preferred are glycol ethers, particularly diethylene glycol rnonoethyl ether and dipropylene glycol monomethyl ether.

As the crystallisation inhibitor b) which can be used in the invention, the following in particular can be quoted: - polyvinyl pyrrolidone, polyvinyl alcohols, copolymers of Vinyl acetate and of vinyl pyrrolidone, polyethylene glycols, benzyl alcohol, mannitol, glycerol, sorbitol, polyoxy—ethylene sorbitan esters; lecithin, sodium carboxy—methyl cellulose; acrylic derivatives such as methacrylates and others; - anionic surface tension agents such as alkaline stearates, particularly of sodium, potassium or ammonium; calcium stearate, triethanolamine stearate; sodium abietate, alkyl sulphates, particularly sodium lauryl sulphate and sodium cetyl sulphate; sodium dodecyl benzene sulphonate; sodium dioctyl sulpho—succinate; fatty acids, particularly those derived from coconut oil; — cationic surface tension agents such as hydrosoluble quaternary ammonium salts with the formula NR’R”R”’R””, Y‘ in which the R radicals are hydrocarbon radicals, possibly hydroxyls, and Y‘ is an anion of a strong acid such as the halogenide anions, sulphate and sulfonates; cetyl trimethyl ammonium bromide is among the cationic surface tension agents which can be used; — amino salts with the formula W R’R”R”’ in which the R radicals are hydrocarbon radicals, possibly hydroxyls; octadecyl amine chlorohydrate is among the cationic surface- agents which can be‘ used; - non ionic surface tension agents such as esters of sorbitan, possibly polyoxy—ethylenated, in particular Polysorbate 80, the ethers of polyoxy-ethylene alkyl; polyethylene glycol stearate, polyoxy-ethylene derivatives of castor oil, polyglycerol esters, fatty polyoxy—ethylene alcohols, fatty polyoXy—ethylene acids, copolymers of ethylene oxide and of propylene oxide; - amphoteric surface tension agents such as the substituted lauryl compounds of betaine, or preferably a mixture of at least two of them.

In a particularly preferred way, a crystallisation inhibitor pair will be used, ie. a combination of a film—creating agent of the polymeric type and a surface tension agent. These agents will be chosen particularly from among the compounds quoted as a crystallisation inhibitor b).

Among the fihn-creating agents of the polymeric type which are particularly worthwhile, the following can be quoted: - different grades of polyvinyl pyrrolidone; — polyvinyl alcohols, and - vinyl acetate and vinyl pyrrolidone copolymers.

With regard to the surface tension agents, non ionic surface tension agents are especially quoted, preferably polyoxy ethylene sorbitan esters and in particular the various grades of Polysorbate, for example Polysorbate 80.

A f1hr1—creating agent and a surface tension agent can in particular be incorporated in close or identical quantities within the limit of the total quantities of crystallisation inhibitor mentioned elsewhere.

The pair thus constituted ensures remarkably well the objectives of having no crystallisation on the animal’s coat and of keeping the appearance of the coat attractive, i.e. without any tendency to stick together or look sticky despite the strong concentration of active material.

As cosolvent d) the following in particular can be quoted: absolute ethanol, isopropanol (propanol 2), methanol.

As the anti-oxidising agent, traditional agents are particularly used such as: butyl hydroxy—anisole, butyl hydroxy—toluene, ascorbic acid, sodium meta—bisulphite, propyl gallate, sodium thiosulphate, a mixture of two of them at the most.

The compositions according to the invention are usually prepared by simply mixing ingredients such as those defined previously; there is an advantage in starting by mixing the active material in the main solvent and then adding the other ingredients or additives.

The subject of this invention is also a method of treating and/or protecting qirevention) animals against parasites, according to which an effective composition according to the invention is applied on a limited area of the animal, as has been described above. The composition is advantageously applied at two points and/or on the back between the animal’s shoulders.

The object of the method can be non therapeutic if it is a question of cleaning the hair and skin of animals while eliminating parasites present as well as their residue and dejecta.

Therefore, the animal has a coat which is pleasing to the eye and to the touch. That also avoids the development of fleas in the home.

The object can also be therapeutic when it is a question of treating parasitosis before pathogenic consequences arise.

The volume applied can be in the region of 0.3 to 1 ml, preferably in the region of 0.5 ml for a cat and in the region of 0.3 to 3 ml for a dog, depending on the weight of the animal.

The volume of the composition applied corresponds preferably to a dose of the compound in formula (1) between 0.3 and 60 mg, particularly between 5 and 15 mg per kg.

The following examples, given as non limitative, illustrate the invention and show how it can be put to use.

Examples 1 to 12: The compositions in the example 1 to 12 are given in the following table: Example No. 1 2 3 4 5 6 7 8 9 10 11 12 Activegprinciple 10 10 10 10 10 10 10 10 10 10 10 10 Ethanol c.c.(g) 10 7.5 15 10 10 10 10 7.5 15 10 10 10 Polyvinyl pyrrolidone (g) 5 5 5 5 5 7.5 5 5 5 5 5 7.5 Polysorbate 80 (g) 5 5 5 5 5 5 5 S 5 5 5 5 Butylhydroxy- anisole (g) 0.02 0.02 0.02 0 0.02 0 0.02 0.02 0.02 O 0.02 O Butylhydroxyl toluene (g) 0.01 0.01 0.01 0.01 0.01 0 0.01 0.01 0.01 0.010.01 0 Diethylene gly- col rnonoethyl ether (c.c.) qty. reqd.for 100 c.c. 0 Dipropylene glycol mono- methyl ether (c.c.) O qty. reqd. for 100 c.c.

As an example, the quantity of diethylene glycol monoethyl ether required is approximately 75 c.c. for the formula in example 1.

Mix together by stirring: ' g of active principle 1-(4-CF3 2,6-C12 phenyl] 3-cyano 4-[CF3-SO-] 5-NH, pyrazole, all of the ethanol, 60 c.c. of diethylene glycol monoethyl ether or of dipropylene glycol monomethyl ether (solvents), all of the polyvinyl pyrrolidone (Kollidon® 17PF from BASF, Germany), all of the Polysorbate 80 (Tween® from ICI), all of the butyl hydroxy-anisole (if present) all of the butyl hydroxy-toluene (if present).

Top up to 100 c.c. with diethylene glycol monoethyl ether or dipropylene glycol monomethyl ether (for example 1 that corresponds to the remaining volume of around 15 c.c.

Each mixture constitutes a concentrated S solution.

Three dogs, Weighing around 7, 14 and 28 kg respectively, are infested with 100 fleas each. Two days after they are treated by “spot on” or “pour on” application of an S solution at the rate of 0.1 ml/kg, in localised form over approximately 5 sq.cm. between the shoulders at the level of the ridge between the shoulder blades. After 24 hours, the time required for complete drying, the appearance of the dogs’ coats in the area where the application was made and elsewhere is identical with the initial appearance. In particular, the animal’s coat is neither tacky nor sticky in contact with the hand and the coat does not contain any bristly tufts. hours after treatment, the dogs are combed so as to remove and count any fleas which may be present. Then at weekly intervals after treatment, the animals are reinfested in the same way as before. 24 hours after each experimental reinfestation, combing is done again to remove and count any fleas which may still be present. Over a period of weeks one finds a percentage of reduction of the flea population which keeps above 95% compared with a pilot group which has not been given the treatment covered by the invention.

Examples 12 to 24: For examples 12 to 24 all that is required is to replace, in the preceding table, examples 1 to 12 with 12 to 24 respectively, with 12.5 g of active principle. The quantities of the other ingredients do not change, apart from the quantity of solvent necessary for making up the quantity to 100 c.c.

Simply by stirring or shaking, mix the following ingredients together: .5 g ofthe compound in example 1, all of the ethanol, 60 c.c. of diethylene glycol monoethyl ether or of dipropylene glycol monomethyl ether, all of the polyvinyl pyrrolidone, all of the Polysorbate 80, all of the butyl hydroxy-anisole (if present), all of the butyl hydroxy—to1uene (if present).

Top up to 100 c.c. with diethylene glycol rnonoethyl ether or dipropylene glycol monomethyl ether.

Used under the conditions described in example 1, these mixtures lead to comparable results. A reduction in the flea population above 95% is noted in less than 24 hours compared with the pilot group.

Claims (21)

CLAIMS :

1. Composition useful for treating and protecting pets infested or likely to be infested with parasites, characterised in that it comprises, in the form of a ready—to—use solution: 5 a) an active insecticidal material with the fonnula (I) 10 y) (1).; in which: R 1 is an atom of halogen, CN or methyl; 15 R2 is S(O),; R3 or 4,5-dicyano-imidazole 2-yl or haloalkyl; R3 is alkyl or haloalkyl; R4 represents a hydrogen or halogen atom; or a radical NRSR6 , S(O),,,R7 , C(O)R7 , or C(O)OR7 , alkyl, haloalkyl or OR9 with a radical -N=C(R9 )(R10); 20 R5 and R6 represent independently the hydrogen atom, of an alkyl, haloalkyl, C(O)a1kyl, S(O), CF3, acyl or alkoxy-carbonyl radical; or R5 and R6 can together fonn a divalent alkylene radical which can be interrupted by one or two divalent hetero—atoms such as oxygen or sulphur; R7 represents an alkyl or haloalkyl radical; R8 represents an alkyl, haloalkyl radical or a hydrogen atom; 25 R9 represents an alkyl radical or a hydrogen atom; Rm represents a phenyl or hetero-aryl group possibly substituted by one or more halogen atoms or groups such as CH, -O-alkyl, -S-alkyl, cyano or alkyl; Y represents a halogen atom, a haloalkyl or haloalcoxy radical, for example lower halcalcoxy, SF 5, with the possibility that: - Y is CN or NO, in positions 2 and 6; — the carbon in 2 of the phenyl radical is replaced by N; - Y is S(O)qCF3 in position 4, but preferably haloalkyl, haloalcoxy or S175; m, n, q, r represent, independently of each other, a whole number equal to O, 1 or 2; p is a whole number equal to 1, 2, 3, 4 or 5, preferably equal to 1, 2 or 3, particularly 3; with the reservation that, when R, is methyl, then R, is haloalkyl, R4 is NH2, p is 2, Y in position 6 is Cl, Y in position 4 is CF3, and the carbon in position 2 of the phenyl is replaced by N; or else R, is 4,5 dicyano imidazole 2-yl, R4 is Cl, p is 3, Y in position 6 is Cl, Y in position 4 is cm, and the carbon in position 2 of the phenyl is replaced by =C-Cl; b) a crystallisation inhibitor which meets the test whereby: 0.3 ml of a solution A comprising 10% (weight:volume) of the compound in formula (I) in the solvent defined under a) below, as well as 10% of this inhibitor, are deposited on a glass plate at 20°C for 24 hours, following which fewer than 10 crystals, and preferably no crystals, are observed with the naked eye on the glass plate; c) an organic solvent with a dielectric constant between 10 and 35, preferably between 20 and 30; d) an organic cosolvent with a boiling point below 100°C, preferably below 80°C, and a dielectric constant between 10 and 40, preferably between 20 and 30;

2. Composition according to Claim 1, characterised in that the compound in formula (I) is present at the rate of 1 to 20% weightzvolume, preferably from 5 to 15%, in the composition. 16

3. Composition according to Claim 1 or 2, characterised in that the crystallisation inhibitor is present at the rate of l to 20% weightzvolume, preferably fi'om 5 to 15%, in the composition.

4. Composition according to one of the Claims 1 to 3, characterised in that the organic solvent represents the complement to 100% of the composition.

5. Composition according to one of the Claims 1 to 4 characterised in that the organic cosolvent is present in the composition at the rate of a Weightzweight cosolvent d):solvent 0) ratio between 1:15 and 1:2 inclusive.

6. Composition according to one of the Claims 1 to 5, characterised in that the water is present at the rate of 0 to 30% volume:Volume, preferably fiom 0 to 5%, in the composition.

7. Composition according to any one of the Claims 1 to 6, characterised in that it includes an anti—oxidising agent.

8. Composition according to Claim 7, characterised in that the anti—oxidising agent is present at the rate of 0.005 to 1% (weightzvolume), preferably from 0.01 to 0.05%.

9. Composition according to one of the Claims 1 to 8, characterised in that the solvent c) is selected from among the group consisting of: acetone, acetonitrile, benzylic alcohol, butyl diglycol, dimethyl acetamide, dimethyl formamide, n—butyl ether of dipropylene glycol, ethanol, isopropanol, methanol, ethylene glycol, monoethyl ether, ethylene glycol monomethyl ether, monomethyl acetamide, monomethyl ether of dipropylene glycol, liquid polyoxy—ethylene glycols, propylene glycol, 2—pyrrolidone, l7 particularly N—methyl pyrrolidone, diethylene glycol monoethyl ether, ethylene glycol, diethyl phthalate, and a mixture of at least two of them.

10. Composition according to one of the Claims 1 to 9, characterised in that the crystallisation inhibitor is selected from among the group consisting of: - polyvinyl pyrrolidone, polyvinyl alcohols, copolymers of vinyl acetate and of vinyl pyrrolidone, polyethylene glycols, benzyl alcohol, mannitol, glycerol, sorbitol, polyoxy—ethylene sorbitan esters; lecithin, sodium carboxy—methyl cellulose; acrylic derivatives such as methacrylates and others; — anionic surface—tension agents such as alkaline stearates, particularly of sodium, potassium or ammonium; calcium stearate, triethanolamine stearate; sodium abietate; alkyl sulphates, particularly sodium lauryl sulphate and sodium cetyl sulphate; sodium dodecyl benzene sulphonate; sodium dioctyl sulpho-succinate; fatty acids, particularly those derived from coconut oil; - cationic surface tension agents such as hydrosoluble quaternary ammonium salts with the formula N'R’R”R”’R””,Y' in which the R radicals are hydrocarbon radicals, possibly hydroxyls, and Y‘ is an anion of a strong acid such as the halogenide, sulphate anions and sulfonates, cetyl trimethyl ammonium bromide; - amino salts with the formula N“ R”’R”R’” in which the R radicals are hydrocarbon radicals, possibly hydroxyls; octadecyl amine chlorohydrate; — non ionic surface tension agents such as esters of sorbitan, possibly polyoxy—ethylenated, in particular Polysorbate 80, the ethers of polyoxy—ethylene alkyl; polyethylene glycol stearate, polyoxy—ethylene derivatives of castor oil, polyglycerol esters, fatty polyoxy—ethylene alcohols, fatty polyoxy—ethylene acids, copolymers of ethylene oxide and of propylene oxide; - amphoteric surface tension agents such as the substituted lauryl compounds of betaine, and preferably mixtures of at least two of them.

11. Composiiton according to one of the Claims 1 to 10, characterised in that, as the crystallisation inhibitor agent, it includes a crystallisation inhibitor pair including a polymeric filrn-creating agent and a surface tension agent.

12. Composition according to Claim 11, characterised in that the polymeric film-creating agent is chosen fiom among the group consisting of: - different grades of polyvinyl pyrrolidone; - polyvinyl alcohols; and - copolymers of Vinyl acetate and of vinyl pyrrolidone.

13. Composition according to Claim 11 or 12, characterised in that the surface tension agent is a non ionic surface tension agent.

14. Composition according to Claim 13, characterised in that the surface tension agent is an ester of polyoxy-ethylene sorbitan such as Polysorbate.

15. Composition according to Claim 14, characterised in that the crystallisation inhibitor is a mixture of polyvinyl pyrrolidone and Polysorbate, preferably Polysorbate 80.

16. Composition according to any one of the Claims 1 to 15, characterised in that the solvent (1) is a glycol ether. 19

17. Composition according to Claim 16, characterised in that the solvent c) is selected from the group consisting of diethylene glycol monoethyl ether and dipropylene glycol monoethyl ether.

18. Composition according to one of the Claims 1 to 17, characterised in that the cosolvent d) is selected from among the group consisting of: absolute ethanol, isopropanol, methanol.

19. Composition according to one of the Claims 1 to 18, characterised in that it includes an anti—oxidising agent selected from among the group consisting of: butyl hydroxy-anisole, butyl hydroxy-toluene, ascorbic acid, sodium meta-bisulphite, propyl gallate, sodium thiosulphate and a mixture of two of them at the most.

20. Composition according to any one of the Claims 1 to 19, characterised in that the insecticidal material complies with the formula (II): in which: R, is a halogen, CN or methyl atom; R2 is S(O) HR 3 or 4,5—dicyanoimidazole 2-yl or haloalkyl; R3 is alkyl or haloalkyl; R4 represents a hydrogen or halogen atom; or an NR5 R6, S(O)m R7 , C(O)R7 radical, or C(O)OR7, alkyl, haloalkyl or OR, or a —N=C(R9)(R,0) radical; R5 and R6 represent independently the hydrogen atom or an alkyl, haloalkyl, C(O)alkyl, S(O), CF, or alkoxycarbonyl radical; or R5 and R6 can together form a divalent alkylene radical which can be interrupted by one or two divalent hetero-atoms such as oxygen or sulphur; R7 represents an alkyl or haloalkyl radical; R8 represents an alkyl, haloalkyl radical or a hydrogen atom; R9 represents an alkyl radical or a hydrogen atom; R10 represents a phenyl or hetero—aryl group, possibly substituted by one or more halogen atoms or groups such as OH, -O-alkyl, -S-alkyl, cyano, or alkyl; R“ and R12 represent, independently of each other, an atom of hydrogen or of halogen and possibly CN or N02, but H or halogen are preferred; R13 represents a halogen atom or a haloalkyl group, haloalkoxy, S(O)q CF3 or SF 5; m, n, q, r represent, independently of each other, a whole number equal to 0, l or 2; X represents a trivalent nitrogen atom or a C-R12 radical, the other three valences of the carbon atom forming part of the aromatic cycle; with the reservation that, when R, is methyl, when or in any case R3 is haloalkyl, R, is NH2, R1, is Cl, R13 is CF3, and X is N; or in any case R2 is 4,5 dicyano imidazole 2-yl, R4 is Cl, R“ is Cl, R13 is CF3, and X is =C—Cl;

21. Composition according to any one of the Claims 1 to 20, characterised in that the compound in formula (I) or (II) is l-[4-CF3 2,6-C12 phenyl] 3-cyano 4-[CF3—SO) 5—NH2 pyrazole. F. R. KELLY & CO., AGENTS FOR THE APPLICANTS