OA20240A - Insecticidal formulation for vector and pest control with increased contact efficacy. - Google Patents
Insecticidal formulation for vector and pest control with increased contact efficacy. Download PDFInfo
- Publication number
- OA20240A OA20240A OA1202100283 OA20240A OA 20240 A OA20240 A OA 20240A OA 1202100283 OA1202100283 OA 1202100283 OA 20240 A OA20240 A OA 20240A
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- OA
- OAPI
- Prior art keywords
- active ingrédient
- insecticidal
- matrix material
- insecticidal active
- température
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Abstract
The present invention relates to insecticidal formulations for vector and pest control with increased contact efficacy, more particularly to insecticidal active ingredient - matrix particles and insecticidal compositions comprising such insecticidal active ingredient - matrix particles, as well as to methods and uses of such insecticidal formulations.
Description
Insecticidal Formulation for Vector and Pest Control with Increased Contact Efficacy
Background of the Invention
The use of pesticides to protect fruits, vegetables and other agricultural crops against insects is well established. Next to these applications the same type of active ingrédients can be used to protect people against vector transmitting insects such as e.g. mosquitos (vector control) and 5 insects e.g. such as cockroaches, flies and bed bugs that are described as hygiene pests outside the agricultural environment.
To protect people against these insects, surfaces in and around the living & food production environment ofthe people are treated with an insecticide. Since contact times are often only short a relative fast uptake of the insecticide is required. In contrast to many agricultural applications 10 the mechanism for control for the active ingrédient in these types of applications is restricted to contact efficacy. No oral uptake will take place when for example mosquitos land and walk on treated surfaces. Consequently, only limited types of pesticides are effective for these treatments. Examples are pyrethroids, carbamates, organophosphates and DDT. Evidently, the latter three are not preferred because of their toxicological profile for human beings and the environment.
Pyrethroids on the other hand hâve been used in vector control and professional pest management very extensively over the last décades with the resuit that strong résistance against this mode of action is establishing.
Some other insecticidal active ingrédients show efficacy and even résistance breaking potential for vector control and professional pest management relevant pests. However, because of their 20 physicochemical properties they show only limited contact efficacy. The high melting point and molecular weight of such insecticidal active ingrédients entail that they hâve a tendency to form highly crystalline structures that are poorly soluble. Consequently, the uptake in the insect via contact is very limited and the insects cannot be efficiently treated with known formulations such as e.g. a conventional suspension concentrate formulation in which the insecticidal active 25 ingrédient is présent as a crystalline entity.
The use of polymers and/or waxes as matrix material, on the other hand, is known in agricultural formulations. Many “controlled release” formulations are based on this principle and hâve been described in the literature. US20060193882A, for example, discusses a formulation where an agrochemical active ingrédient is included in a polymer matrix in order to prolong the residual
-2 biological efficacy. However, with this measure the initial biological efficacy is reduced. Low initial biological efficacy goes along with low contact efficacy and therefore, such “controlled release” formulations are in general not useful for the purpose to increase the contact efficacy of an insecticidal active ingrédient whenever only short contact times occur.
Description of the Invention
The purpose of the présent invention was therefore to provide technical formulation means to solve the issues identified in the prior art and in particular to exploit the full contact and initial (fast knock-down after contact) biological efficacy potential of insecticidal active ingrédients with challenging physicochemical properties. A particular purpose was to provide technical formulation means for insecticidal active ingrédients that hâve high tendency to crystallize under normal conditions but that generally hâve a higher biological activity against pests in the amorphous State. A further purpose was to provide technical formulation means for pest control, in particular cockroaches, mosquitos, flies, bed bugs etc., with high biological contact efficacy on various surfaces such as e.g. fiat, porous or muddy surfaces. Another purpose was to provide technical formulations means for pest control with a résistance breaking potential, in particular with pyrethorid résistance breaking potential.
It has now been found that the purpose has been addressed and a solution is provided with the insecticidal active ingrédient -matrix particles as further described hereinafter.
The insecticidal active ingrédient - matrix particles of the invention relate to insecticidal active ingrédient - matrix particles with a particle size d50 of 0.1 to 75 microns comprising
a) at least one insecticidal active ingrédient with a melting point of equal or above 110°C and a water solubility of equal or below 0.1% and wherein at least one insecticidal active ingrédient is distributed in
b) a matrix material comprising polymerized monomer units selected from the group of C7 to C12 unsaturated aromatic hydrocarbons.
The insecticidal active ingrédient - matrix particles of the invention hâve preferably a particle size of between 0.1 to 75 microns and more preferably between 0.5 and 50 microns and even more preferably between 1 and 25 microns. The D50 value is preferably determined by laser diffraction after dispersion of the insecidical active ingrédient - matrix particles of the invention in a water phase.
- 3 The insectieidal active ingrédient - matrix particles of the invention comprise at least one insectieidal ative ingrédient with a melting point of equal or above 110°C, preferably equal or above 120°C, more preferably equal or above 130°C and even more preferably equal or above 140°C and even more preferably equal or above 150°C; and a water solubility of equal or below 5 0.1%, preferably equal or below 0.01%, more preferably equal or below 0.005% and even more preferred equal or below 0.001%. In another preferred embodiment of the invention the insectieidal active ingrédient - matrix particles comprise one insectieidal active ingrédient with the above indicated physicochemical properties. The melting points according to the invention are measured under standard conditions (1 atmosphère). Water solubility are indicated in 10 percentage referring to the quotient of (g) gram insectieidal active ingrédient /100ml water. Water solubility is preferably measured with liquid chromatography e.g. with a HPLC-MS system (at 20°C, 1 atmosphère and pH 7, see also example 1 as a reference).
According to a preferred embodiment of the invention, the “at least one” insectieidal active ingrédient of the invention comprises at least one amide Chemical moiety.
More preferably the at least one insectieidal active ingrédient of the invention is selected from the Chemical classes of isoxazolines, meta-diamides, arylpyrazolheteroarylamides and arylpyrazolarylamides and/or is active on the γ-aminobutyric acid (GABA) receptor.
The isoxazolines are a class of compounds, which are active against arthropods and insects relevant in the field of plant protection as well as ectoparasites on animais. They are antagonists 20 of the γ-aminobutyric acid (GABA) receptor. The binding site of the isoxazolines is at least partly different from the ones of the cyclodienes and fipronil. (W. L. Shoop et al. Veterinary Parasitology 2014, 201, 179 - 189; T. L. McTier et al. Veterinary Parasitology 2016, 222, 3- 11; K. Nakahira et al. Pest Management Science 2015, 71, 91 - 95; L. Rufener et al. Parasites & Vectors 2017, 10, 530. Prominent représentatives of this class are e.g. lotilaner, sarolaner, 25 fluralander, afoxolaner and 4-[(5S)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5dihydro-l,2-oxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-l,2-oxazolidin-4-yl]-2-methylbenzamide (CAS 1309959-62-3).
The meta-diamides are a class of compound which act as antagonist on the γ-aminobutyric acid (GABA) receptor. A prominent représentative of this class is broflanilide. The binding site of 30 desmethyl-broflanilide is at least partly different from the ones of the cyclodienes and fipronil (T. Nakao, S. Banba Bioorganic & Médicinal Chemistry 2016, 24, 372 - 377).
-4The class of arylpyrazolheteroarylamides and arylpyrazolarylamides that can be preferably used in connection with the présent invention are described in WO 2015/067647A1 and WO 2015/067646A1, which are herewith incorporated by reference. Preferably this class relates to 2chloro-N-cyclopropyl-5-{ l-[2,6-dichloro-4-(l,l,l,2,3,3,3-heptafluoropropan-2-yl)phenyl]-lHpyrazol-4-yl}-N-methylnicotinamide.
In this context, the term “active on the GABA receptor” relates preferably to the characteristic of a Chemical molécule to modulate the GABA receptors physiological activity.
The insecticidal active ingrédients according to the invention may be, depending on the active ingrédient, in the form of géométrie and/or optically active isomers or corresponding isomer mixtures in different compositions. These stereoisomers are, for example, enantiomers, diastereomers or géométrie isomers. Accordingly, the invention encompasses the use of both pure stereoisomers and any mixture of these isomers.
Even more preferably, the at least one insecticidal active ingrédient of the invention is selected from the group of:
2-chloro-N-cyclopropyl-5-{ 1 -[2,6-dichloro-4-( 1,1,1,2,3,3,3-heptafluoropropan-2yl)phenyl]-1 H-pyrazol-4-yl}-N-methylnicotinamide (CAS 1771741 -86-6), broflanilide: 3-[benzoyl(methyl)amino]-N-[2-bromo-4-(l,l,l,2,3,3,3-heptafluoropropan2-yl)-6-(trifluoromethyl)phenyl]-2-fluorobenzamide (CAS 1207727-04-5), 4-[(5S)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-l,2-oxazol-3-yl]N-[(4R)-2-ethyl-3-oxo-l,2-oxazolidin-4-yl]-2-methylbenzamide (CAS 1309959-62-3), 4-[(5R)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-l,2-oxazol-3yl]-N-[(4S)-2-ethyl-3-oxo-l,2-oxazolidin-4-yl]-2-methylbenzamide (CAS 2061933-86-4), 4-[(5S)-5-(3,5-dichloro-4-fluorophenyI)-5-(trifluoromethyl)-4,5-dihydro-l,2-oxazol-3-yl]N-[(4S)-2-ethyl-3-oxo-l,2-oxazolidin-4-yl]-2-methylbenzamide (CAS 1429660-18-3), 4-[(5R)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-l,2-oxazol-3yl]-N-[(4R)-2-ethyl-3-oxo-l,2-oxazolidin-4-yl]-2-methylbenzamide (CAS 1309958-03-9), sarolaner: l-[6-[(5S)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4H-l,2-oxazol3-yl]spiro[lH-2-benzofuran-3,3'-azetidine]-r-yl]-2-methylsulfonylethanone (CAS 1398609-39-6), fluralaner: 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-l,2-oxazol-3-yl]-2-methylN-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]benzamide (CAS 864731-61-3),
- 5 - lotilaner: 3-methyl-N-[2-oxo-2-(2,2,2-trifluoroethylarnino)ethyl]-5-[(5S)-5-(3,4,5trichlorophenyl)-5-(trifluoromethyl)-4H-l,2-oxazol-3-yl]thiophene-2-carboxamide (CAS 1369852-71-0), afoxolaner: 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4H-l,2-oxazol5 3-yl]-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]naphthalene-l-carboxamide (CAS 1093861-60-9),
Even more preferably, the “at least one” insecticidal active ingrédient of the invention is selected from the group of:
2-chloro-N-cyclopropyl-5-{l-[2,6-dichloro-4-(l,l,l,2,3,3,3-heptafluoropropan-210 yl)phenyl]-lH-pyrazol-4-yl}-N-methylnicotinamide (CAS 1771741-86-6), broflanilide: 3-[benzoyI(methyl)amino]-N-[2-bromo-4-(l,l,l,2,3,3,3-heptafluoropropan2-yl)-6-(trifluoromethyl)phenyl]-2-fluorobenzamide (CAS 1207727-04-5), 4-[(5S)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-l,2-oxazol-3-yl]N-[(4R)-2-ethyl-3-oxo-l,2-oxazolidin-4-yl]-2-methylbenzamide (CAS 1309959-62-3).
Most preferably, the “at least one” insecticidal active ingrédient of the invention is selected from the group of 2-chloro-N-cyclopropyl-5-{l-[2,6-dichloro-4-(l,l,l,2,3,3,3-heptafluoropropan-2yl)phenyl]-lH-pyrazol-4-yl}-N-methylnicotinamide (CAS 1771741-86-6) and broflanilide and even more preferably the “at least one” insecticidal active ingrédient is 2-chloro-N-cyclopropyl5-{l-[2,6-dichloro-4-(l,l,l,2,3,3,3-heptafluoropropan-2-yl)phenyl]-lH-pyrazol-4-yl}-N- methylnicotinamide (CAS 1771741-86-6).
In a further embodiment, the insecticidal active ingrédient - matrix particles of the invention comprise at least one of the above described insecticidal active ingrédient distributed and preferably evenly distributed in a matrix material as herein described. The distribution is preferably achieved with a heating step wherein at least one insecticidal active ingrédient and the 25 matrix material are heated at a température where the matrix material is no longer solid, preferably above the softening point of the matrix material but below the melting point of the insecticidal active ingrédient. The mixture is kept at this température (such as e.g. for a time period of 10, 15 or 20 minutes) until the described insecticidal active ingrédient is evenly distributed. The particle size of the insecticidal active ingrédient - matrix particles can be obtained 30 afterwards by conventional milling and/or grinding means with customary mixers, mills and/or grinders.
-6 The matrix material as used for insecticidal active ingrédient - matrix particles of the invention comprise polymerized monomer units selected from the group of C7 to C12 unsaturated aromatic hydrocarbons preferably with a softening point of between 80°C and 130°C and more preferably with a softening point of between 80°C and 115°C and even more preferred of between 80°C and
110°C. The term “softening point” as used herein is referring to the Vicat softening température or Vicat hardness and is the détermination of the softening point for materials that hâve no defmite melting point, such as resins. It is taken as the température at which the specimen is penetrated to a depth of 1 mm by a flat-ended needle with a 1 mm2 circular or square cross-section. Preferably the Vicat B120 test is used to measure the softening point. The Vicat B120 test is characterized by a load of 50 N and a heating rate of 120 (K/h). Standards to déterminé Vicat softening point include ASTM D 1525 and ISO 306, which are largely équivalent.
In a further preferred embodiment of the invention, the matrix material comprises polymerized monomer units selected from the group of C8 to Cl 1 and even more preferred selected from the group of C9 to CIO unsaturated aromatic hydrocarbons. In this context C7 to C12 resp. C8 to 15 Cil, resp. C9 to CIO refers to the amount of carbon atoms that are présent within the molécules.
In another particular preferred embodiment of the invention, the monomer units are selected from the group of indene, methyl indene, vinyltoluene, alpha-methylstyrene, styrene and/or dicyclopentadien. In an even more preferred embodiment the monomer units are selected from the group of indene and methyl indene.
An especially preferred matrix material is a product from the Novares AS, TK, TL, TN, TC, C and CA sériés from the company Rütgers with a softening point of between 80 and 115°C. Even more preferred are Novares Pure 85 AS (Rütgers Group ), Novares C 100 (Rütgers Group), Novares TL 100 (Rütgers Group), Novares TK 100 (Rütgers Group), Novares TN 100 (Rütgers Group) matrix materials.
The polymerization of the monomer units has e.g. been described in EPI900763 Al and is in general known to a person skilled in the art. In a preferred embodiment the polymerization is a cationic polymerization, wherein the weight ratio between the monomer units can vary from matrix material to matrix material. An appropriate matrix material can also be polymerized from one particular monomer unit alone such as e.g. indene (e.g. the Novares C sériés from Rütgers).
Furthermore, the polarity of such a matrix material can be increased by modification with phénol (e.g. the Novares CA sériés from Rütgers; a phénol modified indene matrix material).
- 7Another embodiment ofthe invention refers to an insecticidal active ingrédient - matrix material particle with the above indicated particle size comprising
a) at least one insecticidal active ingrédient with a melting point of equal or above 110°C and a water solubility of equal or below 0.1% and wherein at least one insecticidal active ingrédient is distributed in
b) a matrix material, preferably wherein the matrix material has a softening point that is at least 30°C under the melting point of the at least one insecticidal active ingrédient, characterized in that the insecticidal active ingrédient - matrix material particle does not exhibit a melting peak of the active ingrédient when measured in a second heating cycle after heating to a température of at least 20 °C above the melting point of the at least one insecticidal active ingrédient at a steady heating rate of preferably between 5 to 15 °C per minute and more preferably at 10°C per minute using Differential Scanning Calorimetry.
In this connection a “matrix material”, wherein the matrix material has preferably a softening point that is at least 30°C under the melting point of the at least one insecticidal active ingrédient is preferably selected from a matrix material such as a hydrocarbon resin, more preferably an unsaturated aromatic hydrocarbon resin and even more preferred a C8 to C12 unsaturated aromatic hydrocarbon resin. Such a preferred resin comprise polymerized monomer units selected from C8 to C12 unsaturated aromatic hydrocarbons. An even more preferred matrix material is further described above.
A further embodiment of the invention relates to an insecticidal active ingrédient - matrix material particle as outlined above, characterized in that in the first heating cycle of a Differential Scanning Calorimetry the “at least one” insecticidal active ingrédient and the matrix material are heated to a température of at least 20 °C, preferably at least 20 °C but not more than 50 °C, above the the melting point of the at least one insecticidal active ingrédient at a steady heating rate of preferably between 5° to 15 °C per minute and more preferably at 10°C per minute.
In a preferred version of the Differential Scanning Calorimetry as described above the maximal heating température of the first heating cycle is retained for a period of at least 10 minutes, preferably 15 minutes, more preferably 20 minutes.
In another preferred embodiment of the invention the at least one insecticidal active ingrédient and the matrix material are cooled down to a température of between 0°C to 40°C, preferably of
-8 between 15°C to 35°C, more preferably of between 20°C to 30°C between the first and second heating cycle of the Differential Scanning Calorimetry and preferably also after the second heating cycle each at a steady cooling rate of preferably between 5°C to 15°C per minute and more preferably 10°C per minute.
The term “steady heating rate” as used herein refers to a certain température increase per minute which is keept constant. The température increase over time is therefore preferably linear.
Analogously, the term “steady cooling rate” as used herein refers to a certain température decrease per minute which is keept constant. The température decrease over time is therefore preferably linear.
The term “melting peak” as used herein preferably refers to an endothermie signal in the Differential Scanning Calorimetry (DSC) thermogram. The basic principle underlying this technique is that when the sample undergoes a physical transformation such as phase transitions, more or less heat will need to flow to it than the reference to maintain both at the same température. Whether less or more heat must flow to the sample dépends on whether the process 15 is exothermic or endothermie. For example, as a solid sample melts to a liquid, it will require more heat flowing to the sample to increase its température at the same rate as the reference. This is due to the absorption of heat by the sample as it undergoes the endothermie phase transition from solid to liquid.
A preferred embodiment of the invention relates to an insecticidal active ingrédient - matrix 20 material particle as outlined above, characterized in that in the first heating cycle of a Differential
Scanning Calorimetry the at least one insecticidal active ingrédient and the matrix material are heated to a température of at least 10 °C above the softening point of the matrix material and at least 20 °C below the melting point of the at least one insecticidal active ingrédient at a steady heating rate of preferably between 5° to 15 °C per minute and more preferably at 10°C per minute.
Since the tiles used in a DSC experiment are small and convection / stirring cannot be applied for an adéquate mixing of the components (matrix material and insecticidal active ingrédient) the mixing is only kinetically controlled. This might resuit in a false négative resuit when searching for a compatible matrix material. In the case that such a mixing does not occur spontaneously at a température of at least 10°C above the softening point of the matrix material and at least 20°C below the melting point of the at least one insecticidal active ingrédient, longer waiting times shall be applied (the maximal heating température of the first heating cycle is then preferably retained for a period of at least 30 minutes, more preferably 60 minutes, even more preferably
120 minutes) or alternatively, the first heating cycle is adapted by heating to a température of at least 20 °C above the melting point of the insecticidal active ingrédient to assure an even distribution. An effective method to déterminé if the mixing in the tiles does not occur spontaneously, or whether the matrix material is not suitable, uses the melting enthalpy of the 5 insecticidal active ingrédient. By comparison of the melting enthalpy of the isolated insecticidal active ingrédient with that of a possible peak which occurs during the second heating cycle, the fraction of insecticidal active ingrédient that is dissolved can be determined. In the case that only part of the insecticidal active substance is dissolved, it is preferred that the first heating cycle of the DSC is adapted by heating to a température of at least 20 °C above the melting point of the 10 insecticidal active ingrédient in order to détermine whether the matrix material is suitable.
Another embodiment of the invention relates to an insecticidal active ingrédient - matrix material particle as described herein characterized in that the weight ratio between the at least one insecticidal active ingrédient and the matrix material is from 1:99 to 1:1, preferably between 5:95 to 40:60.
The concentration of the insecticidal active ingrédient in the insecticidal active ingrédient matrix material particle respectively in the resulting insecticidal compositions dépends on the required dose rate of the insecticidal active ingrédient / square meter treated surface. However, such products are typically sprayed with a 10 liter back pack sprayer with which 250 m2 surface can be treated. For such a 10 liter back pack sprayer solution 25 to 250 gram of formulated product 20 preferably 50 to 150 gram of formulated product are used.
The insecticidal active ingrédient concentration per square meter is usually in the range of 1 to 500 mg/m2 and more preferably in the range of 2 to 200 mg/m2.
The molecular weigth of the matrix material according to the invention can vary but is preferably between 1 to 1000 kDa.
A further embodiment of the invention relates to an insecticidal composition, wherein the insecticidal composition comprises
a) an insecticidal active ingrédient - matrix material particle as described herein, preferably from 1 to 70% by weight, more preferably from 5 to 60 % by weight and even more particularly from 10 to 50% by weight,
- 10 b) at least one surfactant(s), preferably at least one nonionic surfactant and/or at least one anionic surfactant, preferably the surfactant(s) are présent from 1 to 25% by weight and more preferably from 2 to 25 % by weight and even more preferably 2.5 to 15% by weight,
c) optionally further adjuvants selected from the group of anti-freeze agents, anti-foam agents, 5 preservatives, anti-oxidants, thickeners, colourants and binders, preferably from 0 to 25% by weight, more preferably from 0.1 to 20% by weight, and even more preferably from 0.5 to 10% by weight;
d) a liquid phase and/or fillers (which in any case add up to 100% per weight of the total insecticidal composition).
Suitable anionic surfactants are ail substances of this type which can usually be employed in agrochemical compositions. As examples are named: alkali métal salts of condensation products of a fatty acid chloride and an aminosulfonic acid, alkali métal salts of fatty alkyl and alkenyl sulfonates and sulfates wherein fatty alkyl and alkenyl includes alkyl and alkenyl groups of from about 8 to 18 carbons, alkali métal alkylbenzene sulfonates having at least 10 carbons in the alkyl group thereof. Preferred members of this class include those having from 10 to about 18 carbons in the alkyl group, ethoxylated alkyl phénols having from about 8 to about 15, preferably from about 8 to about 10, carbons in the alkyl group and about 4 to about 20 oxyethylene units.
Even more preferred anionic surfactants are selected from the group of alkali métal and alkaline earth métal salts of alkylsulphonic acids or alkylarylsulphonic acids. Further even more preferred 20 anionic surfactants are salts of polystyrenesulphonic acids, salts of polyvinylsulphonic acids, salts of naphthalenesulphonic acid/formaldehyde condensâtes, salts of condensâtes of naphthalenesulphonic acid, phenolsulphonic acid and formaldéhyde and also salts of lignosulphonic acid.
Suitable nonionic surfactants are ail compounds of this type which can usually be employed in 25 agrochemical compositions. As examples are named: polyethylene oxide/polypropylene oxide block copolymers, polyethylene glycol ethers of straight-chain alcohols, reaction products of fatty acids with ethylene oxide and/or propylene oxide, furthermore polyvinyl alcohol, polyvinylpyrrolidone, mixed polymers of polyvinyl alcohol and polyvinylpyrrolidone, mixed polymers of polyvinyl acetate and polyvinylpyrrolidone and also copolymers of (meth)acrylic 30 acid and (meth)acrylic esters, furthermore alkyl ethoxylates and alkylaryl ethoxylates which may optionally be phosphated and may optionally be neutralized with bases, polyoxyamine dérivatives and nonylphenol ethoxylates are preferred.
- 11 Suitable anti-freeze agents for the insecticidal composition of the invention are ail those substances which are usually employed for this purpose in agrochemical compositions. Preference is given to urea, glycerol and propylene glycol.
Suitable anti-foam agents for the insecticidal composition of the invention are ail those substances 5 which are usually employed for this purpose in agrochemical compositions. Preference is given to silicone oils and magnésium stéarate.
Suitable preservatives for the insecticidal composition of the invention are ail those substances of this type which are usually employed for this purpose in agrochemical compositions. Examples are Preventol® (from Bayer AG) and Proxel®.
Suitable anti-oxidants for the insecticidal composition of the invention are ail those substances which are usually employed for this purpose in agrochemical compositions. Preference is given to butylated hydroxytoluene (2,6 di-t-butyl 4-methylphenol, BHT).
Suitable thickeners for the insecticidal composition of the invention thickeners are ail those substances of this type which are usually employed in agrochemical compositions. Preference is given to silicates (such as, for example, Attagel® 50 from Engelhard) or xanthan gum (such as, for example, Kelzan ® S from Kelko).
Suitable colourants for the insecticidal composition of the invention are ail those substances which are usually employed for this purpose in agrochemical compositions. Examples are titanium dioxide, carbon black, zinc oxide and blue pigments and permanent red FGR.
Suitable fillers are ail those substances which are usually employed for this purpose in agrochemical compositions. Preference is given to inert fillers such as inorganic particles or salts, such as carbonates, silicates and oxides, and also organic substances, such as urea/formaldehyde condensâtes. Further examples are ulmer white, étiquette violette chalk, potasium sulfate, diamonium hydrogen phosphate, kaolin, rutile, Silicon dioxide, what is known as highly disperse silica, silica gels, and also natural and synthetic silicates such as montmorillonit, bentonit and chemically modifite versions of these clays, furthermore talc. Prefered inert fillers are carbonates such as ulmer white, étiquette violette chalk, silicates such as kaolin, and salts such as potasium sulfate.
- 12 Suitable binders for the insecticidal composition of the invention are ail those substances which are usually employed for this purpose in agrochemical compositions. Examples are polyvinylpyrrolidone, such as Sokalan K 30 or Sokalan K 90.
Preferred insecticidal compositions are in the form of a suspension concentrate (SC), water5 dispersable granule (WG) or wettable powder (WP) or a spray solution thereof.
In general, it has been surprisingly found that the insecticidal compositions according to the invention remain stable even after prolonged storage (2 weeks) at elevated températures (54°C) or in the cold and no crystal growth has been observed. By dilution with water, SC, WG or WPs can be converted into homogeneous spray solutions.
For a suspension concentrate (SC) formulation e.g. a liquid phase is necessary which is preferably water.
For an SC formulation based on the insecticidal active ingrédient - matrix material particles of the invention, the insecticidal composition does preferably comprise one or more surfactant(s), preferably from 2 to 20 % by weight, more preferably 2.5 to 10 % by weight.
For an SC formulation, the insecticidal composition does preferably comprise (as feature (c)) adjuvants selected from the groups of anti-freeze agents, anti-foam agents, preservatives, antioxidants and thickeners, preferably from 0.1 to 20% by weight.
The SC formulation according to the invention are prepared by mixing the particular desired ratios of the components with one another. The components may be mixed with one another in 20 any order; if a thickener is présent it is preferably added after the milling process. Expediently, the solid components are employed in a fine ground State. However, it is also possible to subject the suspension formed after mixing of the components initially to a coarse grinding then to a fine grinding to achieve the particle size d50 of the insecticidal active ingrédient - matrix material particles and the same d50 for the other components. The SC formulation has therefore a particle 25 size d50 of ail components of 0.1 to 75 microns, more preferably between 0.5 and 50 microns and even more preferably between 1 and 25 microns. Suitable for carrying out the préparation of an SC are customary mixers, mills and grinders employed for producing agrochemical formulations.
- 13 When preparing the SC formulation the températures may be varied within a certain range. In general, the process is carried out at températures between 10°C and 60°C, preferably between 15°C and 45°C and under normal pressure.
For a wettable powder (WP) formulation fillers are necessary.
For a WP formulation, the insecticidal composition does preferably comprise as one or more surfactant(s) (as feature (b)), preferably from 2 to 25 % by weight, more preferably 2.5 to 15% by weight.
For a WP formulation, the insecticidal composition does preferably comprise (as feature (c)) adjuvants selected from the groups of anti-foam agents, preservatives, anti-oxidants, preferably 10 from 0.5 to 10% by weight. The WP formulation according to the invention are prepared by mixing the particular desired ratios of the components with one another. The components may be mixed with one another in any order. Expediently, the solid components are employed in a fine ground State. However, it is also possible to subject the suspension formed after mixing of the components initially to a coarse grinding then to a fine grinding to achieve the particle size d50 15 of ail components of 0.1 to 75 microns, preferably 0.5 and 50 microns and even more preferably between 1 and 25 microns.
Suitable for carrying out the process according to the invention are customary mixers and dry milling devices such as an air yet mill employed for producing agrochemical formulations.
The water-dispersible granule (WG) formulation according to the invention can, for example, be 20 prepared as extrusion granule, fluid bet granule or spray drying granule according to standard methods as applicable in the agrochemical industry. Commonly, the basis for an extrusion granule is a WP type of premix (TK), for the other technologies the basis is a suspension concentrate (slurry). In addition to the described compositions these TK and slurry can hâve as further components the herein described fillers and/or binders.
For a WG formulation, the insecticidal composition does preferably comprise as one or more surfactant(s) (feature (b)), preferably from 2 to 25 % by weight, more preferably 2.5 to 15 % by weight.
For a WG formulation, the insecticidal composition does preferably comprise (as feature (c)) adjuvants selected from the groups of anti-foam agents, preservatives, anti-oxidants, binders, 30 preferably from 0.5 to 10% by weight.
- 14For a WG formulation, the insecticidal composition does preferably comprise (as feature (d)) fillers (which in any case add up to 100% per weight of the total WG formulation).
Another embodiment ofthe invention relates to the us of an insecticidal active ingrédient - matrix material particle as described herein or an insecticidal composition as described herein to control pests in particular insects and/or arachnids (preferably of the subclass Acari), and especially mosquitoes, flies, mites, tickes, lices, ants, termites and cockroaches.
The pests are preferably controlled via contact of the pest with the insecticidal active ingrédient - matrix material particle as described herein or an insecticidal composition as described herein. Preferably no oral uptake is required. The term “control” of the pests refers to the possibility to be able to knock-down, kill and/or repel the pests.
The insecticidal active ingrédient - matrix material particle as described herein or an insecticidal composition as described herein are preferably used outside the agricultural environment and in particular for vector control and professional pest management applications.
For the purpose of the présent invention, a vector is an arthropod, in particular an insect or arachnid, capable of transmitting pathogens such as, for example, viruses, worms, single-cell organisms and bacteria from a réservoir (plant, animal, human, etc.) to a host. The pathogens can be transmitted either mechanically (for example trachoma by non-stinging flies) to a host, or by injection (for example malaria parasites by mosquitoes) into a host.
Examples of vectors and the diseases or pathogens they transmit are:
1) Mosquitoes: Anopheles: malaria, filariasis; Culex: Japanese encephalitis, other viral diseases, filariasis, transmission of other worms; Aedes: yellow fever, dengue fever, other viral diseases, filariasis;
- Simuliidae: transmission of worms, in particular Onchocerca volvulus; Psychodidae: transmission of leishmaniasis
2) Lice: skin infections, épidémie typhus;
3) Fleas: plague, endemic typhus, cestodes;
4) Flies: sleeping sickness (trypanosomiasis); choiera, other bacterial diseases;
5) Mites: acariosis, épidémie typhus, rickettsialpox, tularaemia, Saint Louis encephalitis, tickborne encephalitis (TBE), Crimean-Congo haemorrhagic fever, borreliosis;
6) Ticks: borellioses such as Borrelia burgdorferi sensu lato., Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), babesioses (Babesia canis canis), ehrlichiosis.
- 15 Examples of vectors in the sense of the présent invention are insects, for example aphids, flies, leafhoppers or thrips, which are capable of transmitting plant viruses to plants. Other vectors capable of transmitting plant viruses are spider mites, lice, beetles and nematodes.
Further preferred examples of vectors in the sense of the présent invention are insects and arachnids such as mosquitoes, in particular of the généra Aedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, psychodids such as Phlebotomus, Lutzomyia, lice, fleas, flies, mites and ticks capable of transmitting pathogens to animais and/or humans.
The insecticidal active ingrédient - matrix material particle as described herein or an insecticidal composition as described herein are suitable for use in the prévention of diseases and/or pathogens transmitted by vectors. Thus, a further aspect of the présent invention is the use of active compound combinations according to the invention for vector control, for example in agriculture, in horticulture, in gardens and in leisure facilities, and also in the protection of materials and stored products.
Furthermore , the insecticidal active ingrédient - matrix material particle as described herein or an insecticidal composition as described herein are suitable for professional pest management applications against common pests occurring in household situation and public/commercial premises such as cockroaches, mosquitoes, ants, mites, flies, stored product pests, occasional pests, termites etc.
Professional pest management is conducted to reduce pest numbers to an acceptable level by use of various strategies.
Examples of common types of pests found in or arround households and pulic/commercial premises are:
1) Cockroaches: American cockroach (Periplaneta americana), German cockroach (Blatella germanica), brown banded cockroach (Supella longipalpa), oriental cockroach (Blatta orientalis)
2) Mosquitos (cf. Vector control)
3) Ants: black house ant; odorous garden ant; fire ant/red imported fire ant; ghost ant; pharaoh Ant; white footed ant
4) Mites: dust mites, dirt mites,
- 165)
Flies: filth Aies or housefly and its relatives (Muscidae); flesh flies (Sarcophagidae); bottle flies and blowflies (Calliphoridae); black flies (Simuliidae); horseflies and deer flies (Tabanidae), fruit flies (Drosophilidae)
6) Stored Product Pests: primary coleopteran (beetles) pests include grain weevils (Sitophilus granarius, S. zeamais, S. oryzae), the lesser grain borer (Rhyzopertha dominica) and the saw-toothed grain beetle (Oryzaephilus surinamensis); secondary beetle pests include the flour beetles (Tribolium castaneum and T.confusum); the main lepidopteran pests (moths) are secondary; they feed regularly on processed foods so are more common in domestic kitchens and larders.
7) Occasional pests: silverfish, millipedes, psocids/ booklice, clothes moths, plaster bagworms, phorid flies, dog ticks, flea, carpet beatle, black carpet beetle
8) Termites: Odontotermes spp., Microcerotermes spp., Coptotermes spp., Heterotermes spp., Reticulitermes spp., Zootermopsis spp., Cryptotermes spp., Incisitermes spp., Marginitermes spp. etc.
Another embodiment of the invention relates to a method to control pests with an insecticidal active ingrédient - matrix material particle as described herein or an insecticidal composition as described herein.
Another embodiment of the invention relates to method to identify a useful matrix material for an insecticidal composition with Differential Scanning Calorimetry as follows:
a) an insecticidal active ingrédient with a melting point of equal or above 110°C and a water solubility of equal or below 0.1% and a matrix material to be tested are heated to a température of at least 20 °C (preferably at least 20 °C but no more than 50 °C) above the melting point of the at least one insecticidal active ingrédient at a steady heating rate of preferably between 5°C to 15 °C per minute and more preferably 10°C per minute in a first heating cycle of the Differential Scanning Calorimetry,
b) the maximal heating température of the first heating cycle is retained for a period of at least 10 minutes, preferably at least 15 minutes and more preferably at least 20 minutes,
c) the température is then cooled down to a température of between 0°C to 40°C (preferably 15°C to 35°C, more preferably to 20°C to 30°C),
d) in a second heating cycle step, the température is raised to a température of at least 20 °C above the melting point of the at least one insecticidal active ingrédient at a
- 17steady heating rate of preferably between 5° to 15 °C per minute and more preferably at 10 °C per minute,
e) a useful matrix material is identifïed in case that the insecticidal active ingrédient matrix material combination does not exhibit a melting peak when measured in the second heating cycle of the Differential Scanning Calorimetry.
Particularly preferred matrix materials are identifïed with DSC as indicated above when the first step a) is performed as follows:
Step a): an insecticidal active ingrédient with a melting point of equal or above 110°C and a water solubility of equal or below 0.1% and a matrix material to be tested (preferably with a softening point of at least 30°C under the melting point of the insecticidal active ingrédient) are heated to a température of (preferably at least 10 °C above the softening point of the matrix material and) at least 20 °C below the melting point of the at least one insecticidal active ingrédient at a steady heating rate in a first heating cycle ofthe Differential Scanning Calorimetry. However, as indicated above, such a procedure might resuit in a false négative resuit when searching for a compatible matrix material. Therefore, it is then also needed to adapt step e) of the above indicated method preferably as follows:
Step e): a useful matrix material is identifïed in case that the insecticidal active ingrédient matrix material combination does not exhibit a melting peak when measured in the second heating cycle of the Differential Scanning Calorimetry or, in case a melting peak of the insecticidal active ingrédients is exhibited, the melting enthalpy of the insecticidal active ingrédient as measured in a DSC (under the same heating conditions) alone is compared with the melting enthalpy of the insecticidal active ingrédient observed during the second heating cycle of the insecticidal active ingrédient matrix material combination in the DSC.
By comparing the différences of the melting enthalpies the fraction of the insecticidal active ingrédient that is dissolved in the matrix material can be determined and therefore the suitability of the matrix can be assessed.
Another embodiment of the invention relates to a method to increase the contact efficacy of an insecticidal active ingrédient with a melting point equal or above 110°C and a water solubility of equal or below 0.1% with an insecticidal active ingrédient - matrix material particle as described herein or an insecticidal composition as described herein in comparison to a conventional suspension concentrate formulation with the same insecticidal active ingrédient.
- 18 A conventional suspension concentrate (SC) formulation refers to a dispersion in water. Such conventional SC formulations are known to be useful for active ingrédients with a high melting point and insolubility in water. Conventional suspension concentrâtes are usually made by premixing the active ingrédient powder in an aqueous solution of a wetting agent and a dispersing 5 agent, followed by a wet grinding process in a bead mill to give a particle size distribution in the range of 1 to 10 microns. Then, other materials can be added such as e.g. a thickener in order to modify the rheological properties of the system to reduce the extend of particle séparation and settling on storage. Typical wetting agents/dispersing agents used in conventional SC formulations are sodium lignosulphonates, sodium naphthalene sulphonate-formaldehyde 10 condensâtes, aliphatic alcohol ethoxylates, tristryrylphenol ethoxylate phosphate esters, EO/PO block copolymers, graft copolymers. As an anti-freezing agent urea, glycerol or propylene glycol is used. A conventional SC formulation comprises therefore an insectieidal active ingrédient (560 % by weight), a wetting agent and a dispersing agents (2.5-15 % by weight), an anti-freezing agent (4-13 % by weight), other additives such as e.g. a thickener (0.2-2 % by weight), and water 15 (which in any case add up to 100% per weight of the total conventional SC formulation).
The présent invention is illustrated in greater detail with reference to the examples which follow, but is not limited in any way to the use forms described in the examples.
Examples:
1. Représentative Physicochemical Parameters of Insectieidal Active Ingrédients as used 20 according to the Invention
Table 1 :
| Insectieidal Active Ingrédient | Melting point | water solubility at pH 7 |
| broflanilide | 155 °C | < 0.01 mg/1 |
| 4-[(5S)-5-(3,5-dichloro-4fluorophenyl)-5-(trifluoromethyl)-4,5dihydro-1,2-oxazol-3-yl]-N-[(4R)-2ethy 1-3 -oxo-1,2-oxazolidin-4-yl]-2methylbenzamide | 145 °C | < 0.01 mg/1 |
| 2-chloro-N-cyclopropyl-5- {1 -[2,6dichloro-4-(I,l,l,2,3,3,3- | 173 °C | < 0.01 mg/1 |
- 19heptafluoropropan-2-yl)phenyl]-1H pyrazol-4-y 1} -N-methy Inicotinamide
The reported melting points as shown in table 1 were determined under normal conditions (1 atmosphère) with technical grade active ingrédients by differential thermal analysis using a Mettler Toledo 822 or 823 DSC instrument. The sample was heated from 25 °C up to 300 °C at a heating rate of 3 K/min in a perforated aluminum crucible. The melting point is determined by first specifying a baseline for the température range to be evaluated. A tangent is then drawn at the turning point of the endothermie side of the peak and its intersection with the baseline is stated as the melting point of the investigated substance.
The reported water solubilities as shown in table 1 are determined as follows: Préparation of calibration standards: A 1000 ppm solution of the analyte in acetonitrile is prepared and from this at least three calibration points are obtained by dilution with acetonitrile going down to 0.01 mg/L, if needed. Sample Préparation: Two cavities of a deepwell are filled each with about 0.6 mg of homogenized sample and 500 pL of a pH 7 phosphate buffer is added. A glass pearl is added to each cavity, the deepwell is sealed and shaken for at least 24 h at 1600 rpm at 23°C. After the shaking procedure the solution is filtered. Aliquots of the filtrâtes are analysed via a HPLC-MS system with DAD and MS détection. The peak areas of ail selected single DAD and ion traces are taken for the calculations. The calculation is done by external calibration against the areas of the standard samples (linear régression). The mean of ail calculated values gives the water solubility of the active ingrédient.
2. Détermination of the Suitability of a Matrix Material for the Insecticidal Active Ingrédient under Investigation with Differential Scanning Calorimetry (DSC)
Using differential scanning calorimetry (Mettler Toledo DSC 822e or 823 DSC) some mg of matrix material and the insecticidal active ingrédient under investigation are entered into a tile and closed.
The weight ratio between matrix material and insecticidal active ingrédient was as follows:
Table: 2:
| Samples: | Matrix material: | Insecticidal Active Ingrédient: | Weight Ratio (Matrix Material/Insecticidal Active Ingrédient): |
| Sample 1 | Novares CA 100 (Rutgers Group) | 2-chloro-N-cyclopropyl5-{ l-[2,6-dichloro-4(1,1,1,2,3,3,3heptafluoropropan-2yl)phenyl]-1 H-pyrazol4-yl}-Nmethylnicotinamide | 90 : 10 |
| Sample 2 | Novares CA 100 (Rütgers Group) | Broflanilide | 95 : 5 |
| Sample 3 | Novares CA 100 (Rütgers Group) | 4-[(5S)-5-(3,5-dichloro4-fluoropheny l)-5 (trifluoromethyl)-4,5dihydro-l,2-oxazol-3yl]-N-[(4R)-2-ethyl-3oxo-1,2-oxazolidin-4yl]-2-methylbenzamide | 90 : 10 |
| Sample 4 (control) | Licowax 371 FP (from Clariant) | 2-chloro-N-cyclopropyl5-{l-[2,6-dichloro-4(1,1,1,2,3,3,3heptafluoropropan-2yl)phenyl]-1 H-pyrazol4-yl}-N- methy Inicotinam ide | 90:10 |
As reference an empty closed tile was used. After equilibrating in the machine, both tiles are heated according to the following program:
Heating from 25°C to 130°C at a heating rate of 10 °C/min.
Waiting for 20 min
Cooling down to 25°C at a cooling rate of 10 °C/min
Heating from 25°C to 200°C at a heating rate of 10 °C/min
-21 ' · Cooling down to 25°C at a cooling rate of 10 °C/min
In case the weight ratio between the matrix material and insecticidal active ingrédient is not optimal and e.g. too much insecticidal active ingrédient is présent which cannot be evently distributed within the matrix material within the given time using the program above. The 5 content of the insecticidal active ingrédient can be decreased and the program can be run again or maximal heating température can be kept for a longer time period or alternatively, the following program can be applied:.
• Heating from 25°C. to 200°C. at a heating rate of 10 °C/min ( the upper température can be varied, depending on the melting point of the insecticidal active ingrédient to 10 be investigated and should be 20°C above this melting point) • Waiting for 20 min • Cooling down to 25°C. at a heating rate of 10 °C/min • Heating from 25°C. to 200°C. at a heating rate of 10 °C/min ( the upper température can be varied, depending on the melting point of the insecticidal active ingrédient to 15 be investigated and should be 20°C above this melting point) • Cooling down to 25°C. at a heating rate of 10 °C/min
Results: For samples 1 to 3 no melting peak of the insecticidal active ingrédient during the second heating cycle has been identified in the DSC indicating that the matrix material is suitable for the insecticidal active ingrédient investigated. For sample 4 a melting peak of 20 the insecticidal active ingrédient during the second heating cycle has been identified in the
DSC indicating that the matrix material is not suitable for the insecticidal active ingrédient investigated.
In analogy to the above described procedure and program other matrix material insecticidal active ingrédient combinations hâve been investigated with insecticidal active 25 . ingrédients and matrix materials hâve been identified which did not show a melting peak of the insecticidal active ingrédient during the second heating cycle in the DSC as follows:
Insecticidal Active IngfîëSient:- 2-chloro-N-cyclopropyl-5-{l-[2,6-dichloro-4(l,l,l,2,3,3,3-heptafluoropropan-2-yl)phenyI]-lH-pyrazol-4-yl}-N-methylnicotinamide in combination with one of following matrix materials: Novares Pure 85 AS (Rütgers Group
-22), Novares C 100 (Rütgers Group), Novares TL 100 (Rütgers Group), Novares TK 100 (Rütgers Group), Novares TN 100 (Rütgers Group).
3. Préparation of Insecticidal Active Ingrédient - Matrix Particles
40.0 gram of 2-chloro-N-cyclopropyl-5-{l-[2,6-dichloro-4-(l,LL2,3,3,3heptafluoropropan-2-yl)phenyl]-lH-pyrazol-4-yl}-N-methylnicotinamide was added to 60.0 gram of Novares CA 100 (Rütgers Group). This mixture was stirred and heated to a température of 130 °C. The température was kept while stirring until the active ingrédient was evenly distributed. Subsequently the mixture was cooled down to room température.
The obtained matrix active ingrédient composition was mi lied using a mixer with a cutting device (food processor Braun Küchenmaschine 3210).
In analogy to this method the same (or other) insecticidal active ingrédient - matrix particles can be made (also with other concentrations).
4. Préparation of a Water-Dispersable Granule (WP) formulation based on the Insecticidal Active Ingrédient - Matrix Particles as prepared in example 3.
For the préparation of a WP 10, 25 gram of the insecticidal active ingrédient - matrix particles according to example 3 was added into mixer with a cutting device with 5 % per weight of Oparyl MT 804 (Giovanni Bozzetto S.p.A.), 10 % per weight of Baykanol SL (Lanxess) and 60 % per weight of Kaolin Tec (Ziegler & Co. GmbH) and stirred. Subsequently this mixture was milled by air jet milling resulting in a WP containing 10 % insecticidal active ingrédient with the required physicochemical properties.
For the préparation of a WP 20, 50 gram of the insecticidal active ingrédient - matrix particles according to example 3 was added into mixer with a cutting device with 5 % per weight of Oparyl MT 804 (Giovanni Bozzetto S.p.A.), 10 % per weight of Baykanol SL (Lanxess) and 35 % per weight of Kaolin Tec (Ziegler & Co. GmbH) and stirred. Subsequently this mixture was milled by air jet milling resulting in a WP containing 20 % per weight insecticidal active ingrédient with the required physicochemical properties.
For the préparation of a WP 5,50 gram of the insecticidal active ingrédient - matrix particles according to example 3 (based on 10 gram Broflanilide with 90 gram Novaris CA 100 matrix material) was added into mixer with a cutting device with 2 % per weight of Oparyl MT 804 (Giovanni Bozzetto S.p.A.), 5 % per weight of Baykanol SL (Lanxess), 2 % per
-23 weight of Ultrasil VN 3 (Evonik) and 38 % per weight of Kaolin Tec (Ziegler & Co. GmbH) and stirred. Subsequently this mixture was milled by air jet milling resulting in a WP containing 5 % per weight insecticidal active ingrédient with the required physicochemical properties.
5. Préparation of a Suspension concentrate (SC) formulation based on the Insecticidal Active Ingrédient - Matrix Particles as prepared in example 3.
For the préparation of a SC 100, 25 gram of the insecticidal active ingrédient - matrix particles according to example 3 was mixed with 3.0 gram Atlox 4913 (Croda), 10 gram propylene glycol, 0.12 gram Proxel GXL 20 (Lonza), 0.1 gram Silcolapse 426 R (Solvay), 1 gram Synperonic PE/F 127 (Croda), and 1 gram Lucramul PS 16 (Levaco) and the mixture is then stirred until a homogeneous suspension is formed. The homogeneous suspension is subjected initially to coarse grinding and then to fine grinding, resulting in a suspension in which 90% of the solids particles hâve a particle size below 10 pm. Subsequently, 0.4 gram Kelzan (CP Kelco) and 59.38 gram of demineralized water were added at room température with stirring. This gives a homogeneous suspension concentrate.
6. Préparation of Conventional SC Formulations
In order to compare the characterisics of the formulations according to the invention with conventional formulations following conventional SC formulation hâve been prepared: SC formulation with Deltamethrin (SC200), SC formulation (SC25, SC 100) with 2-chloro-Ncyclopropy 1-5- {1 -[2,6-dichloro-4-( 1,1,1,2,3,3,3 -heptafluoropropan-2-yl)pheny 1]-1Hpyrazol-4-yl}-N-methylnicotinamide and an SC wax formulation (SC2.5%) with Deltamethrin.
SC formulation with Deltamethrin and the SC formulation with 2-chloro-N-cyclopropyl-5{1 -[2,6-dichloro-4-( 1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-1 H-pyrazol-4-yi} -Nmethylnicotinamide hâve been prepared as follows: The liquid ingrédients as shown in table 3 were mixed and then solids were added and the mixture is then stirred until a homogeneous suspension is formed. The homogeneous suspension is subjected initially to coarse grinding and then to fine grinding, resulting in a suspension in which 90% of the solids particles hâve a particle size below 10 pm. Subsequently, Kelzan and water are added at room température with stirring. This gives a homogeneous suspension concentrate.
Table 3:
| Ingrédients | SC formulation with 2-chIoroN-cyclopropyl-5-{l-[2,6dichloro-4-(l, 1,1,2,3,3,3heptafluoropropan-2yl)phenyl]-lH-pyrazol-4-yl}-Nmethylnicotinamide (in % by weight) | SC formulation with Deltamethrin (in % by weight) | |
| Formulation: SC25 | Formulation: SC 100 | Formulation: SC 200 | |
| 2-chloro-Ncyclopropyl-5-{l-[2,6dichloro-4(1,1,1,2,3,3,3heptafluoropropan-2yl)phenyl]-lH-pyrazol4-yl}-Nmethylnicotinamide | 2.5 | 10.0 | |
| Deltamethrin | 18.35 | ||
| Atlox 4913 (from Croda) | 3.0 | 3.0 | 4.5 |
| Soprophor TS 54 (from Solvay) | 5.0 | 5.0 | 1.5 |
| Synperonic PE/F 127 (from Croda) | 5.0 | 5.0 | |
| Glycerin | 10.0 | ||
| 1,2-propylene glycol | 10.0 | 10.0 | |
| Silcolapse 426 R (from Solvay) | 0.1 | 0.1 | 0.275 |
| Proxel® GXL 20 (Lonza group) | 0.12 | 0.1 | 0.12 |
| Preventol® D7 (from Lanxess) | 0.08 | ||
| Kelzan (CP Kelco) | 0.4 | 0.4 | 0.24 |
| Citric acid | 0.018 |
Demineralized water
73.88
66.4
64.917
The SC wax formulation (SC 2.5%) with Deltamethrin was prepared according to example 1 according to WO2016/001285A1.
7. Comparison of the Biological Contact Efficacy against Cockroaches with Inventive WP and Conventional SC Formulations
Diluted spray solution was prepared by dissolving a spécifie amount of formulation in tap water.
The WP 20 formulation as prepared according to example 4 containing 20g active ingrédient per 100g formulation was used. 143 mg of the WP 20 formulation was dissolved in 50 ml tap water and transferred to a spray robot that is capable of spraying a volume of 35 ml evenly to an area of one square meter, which corresponds to 20 mg resp. 4 mg active ingredient/m2 (abbreviated as a.i./m2). For surface concentration of 4 mg active ingredient/m2 1:5 dilutions of the stock-solution was made. The surfaces were glazed tiles.
In addition, 0.3ml of the conventional SC 100 formulation as prepared according to example 6 (100g active ingrédient per liter) were added to 49.7ml of tap water. 35 ml of that solution was sprayed with a spray robot onto 1 square meter resulting in the deposit of 20 mg resp. 4 mg. active ingredient/m2. For a surface concentration of 4 mg active ingredient/m2 a 1:5 dilution of the stock-solution was made. The surfaces were glazed tiles.
Control: As a négative control 50ml pure tap water were transferred to the spray robot. 35ml of the tap water were sprayed to an area of 1 square meter. The surfaces sprayed were glazed tiles.
Then, adult Periplaneta americana (American cockroach) insects were placed onto the dried surface of the glazed tiles for 30 min after a 24h drying period. Afterwards the test insect were removed from the surface and transferred to clean containers for further observation. Read-out times for insects were 24 hours, 48 hours and 72 hours after contact to the treated surface. Mortality in percent (%) was measured. In the examples, 100% mortality means that ail test insects were dead, whereas 0% means that no mortality could be observed. The results are shown in table 4.
-26Table 4:
| Test insects: Periplaneta americana (American cockroach) | ||||
| Mortality [%] | ||||
| Formulation | mg a.i. / mz | 24h | 48 h | 72h |
| WP 20 (example 4) | 20 | 100 | 100 | 100 |
| 4 | 20 | 100 | 100 | |
| SC 100 (example 6) | 20 | 33 | 100 | 100 |
| 4 | 0 | 13 | 47 | |
| Control | 0 | 0 | 0 |
8. Comparison of the Biological Contact Effïcacy against Bed Bugs with Inventive WP and 5 Conventional SC Formulations
A similar test as described in example 7 has been performed with Cimex lectularius (bed bugs) instead of American cockroaches and following formulations: A WP 20 as described in example 7.
In addition, 0.3ml of the conventional SC 100 formulation as prepared according to 10 example 6 (100g active ingrédient per liter) were added to 49.7ml of tap water. 35 ml of that solution was sprayed with a spray robot onto 1 square meter resulting in the deposit of 20 mg resp. 4 mg active ingredient/m2. For a surface concentration of 4 mg active ingredient/m2 a 1:5 dilution of the stock-solution was made. The surfaces were glazed tiles.
The control was the same as in example 7. The results are shown in table 5.
Table 5:
-27 Test insects: Cimex lectularius (Bed Bugs)
| Mortality [%] | ||||
| Formulation | mg a.i. / m2 | 24h | 48h | 72h |
| WP 20 (example 4) | 20 | 0 | 60 | 93 |
| 4 | 0 | 7 | 73 | |
| SC 100 (example 6) | 20 | 0 | 0 | 0 |
| 4 | 0 | 0 | 0 | |
| Control | 0 | 0 | 0 |
9. Comparison of the Biological Contact Efficacy against Mosquitos with Inventive WP and Conventional SC Formulations
A similar test as described in example 7 has been performed with Anopheles funestus (Malaria mosquito) instead of American cockroaches. Read-out times for insects were 24 hours after contact to the treated surface. Following formulations hâve been used:
A WP 20 as described in example 7.
A WP 10 formulation containing as prepared in example 4 with 10g active ingrédient per 100g formulation was used. 285 mg of the WP 10 formulation was dissolved in 50ml tap water and transferred to a spray robot that is capable of spraying a volume of 35ml evenly to an area of one square meter, which corresponds to 20 mg resp. 4 mg active ingredient/m2. For surface a concentration of 4 mg active ingredient/m2 a 1:5 dilution of the stock-solution was made.
The surfaces were glazed tiles.
In addition, 1.15ml of the conventional SC 25 formulation as prepared according to example 6 (25g active ingrédient per liter) were added to 48.85ml of tap water. 35 ml of
-28 that solution was sprayed with a spray robot onto 1 square meter resulting in the deposit of 20 mg resp. 4 mg active ingredient/m2. For a surface concentration of 4 mg active ingredient/m2 a 1:5 dilution of the stock-solution was made. The surfaces were glazed tiles.
The control was the same as in example 7. The results are shown in table 6.
Table 6:
Test insects: Anopheles funestus (Malaria mosquito)
| Mortality [%] | ||
| Formulation | mg a.i. / m2 | 24h |
| WP 20 (example 4) | 20 | 100 |
| 4 | 100 | |
| WP 10 (example 4) | 20 | 100 |
| 4 | 100 | |
| SC 25 (example 6) | 20 | 25 |
| 4 | 25 | |
| Control | 0 |
10. Comparison of the Biological Contact Efficacy against Mosquitos with Inventive WP and and Inventive SC Formulations
A similar test as described in example 9 has been performed with Anopheles funestus (Malaria mosquito). However, the formulations hâve been sprayed on glaze tiles via a glass nozzle and compressed air pressure of 0.2 bar. The spray radius was adjusted in a way that 1 ml completely covers the test surface, which corresponds to 20 mg active ingredient/m2. For a surface concentration of 4 mg active ingredient/m2 or 0.8 mg active ingredient/m2 a 1:5 resp. a 1:10 dilution of the stock-solution has been made.
Following formulations hâve been used:
WP 10 as descriped in example 9 resp. in example 4.
A SC 100 as described in example 7 resp. in example 5.
The control was the same as in example 7.
-29The results are shown in table 7.
Table 7:
Test insects: Anopheles funestus (Malaria mosquito)
| Mortality [%] | ||
| Formulation | mg a.i. / m2 | 24h |
| WP 10 (examples 9 and 4) | 4 | 100 |
| 0.8 | 100 | |
| SC 100 (examples 7 and 5) | 4 | 100 |
| 0.8 | 80 | |
| Control | 0 |
In summary examples 7 to 9 show the improved contact biological efficacy of the formulations according to the invention in comparison to conventional formulations with the same active ingrédient.
11. Long Term Efficacy against Mosquitos with Inventive WP Formulations
Glazed tiles and unglazed tiles hâve been treated with the WP 10 and WP 20 formulations 10 as described in example 9 and a WP 5 based on Broflanilide as described in Example 4 and then stored at ambient conditions. An additional set of treated tiles were stored in a climate chamber with conditions of 27°C and 80% air humidity. In monthly contact bioassays it has been shown, that the insecticidal effect of the treated surface remains stable after a period of 28 weeks regardless of the storage conditions. The contact bioassays hâve been 15 conducted as outlined in example 9.
The results are shown in table 8 (The control was the same as in example 7).
Table 8:
Test insects: Anopheles funestus (Malaria mosquito) 28 weeks after spray treatment
Mortality [%]
| Formulation | mg a.i. / m2 | 24h |
| WP 20 (examples 9 and 4) | 20 | 100 |
| 4 | 100 | |
| WP 10 (examples 9 and 4) | 20 | 100 |
| 4 | 100 | |
| WP 5 (example 4) | 20 | 100 |
| 4 | 100 | |
| Control | 0 |
12. Long Term Efficacy against Mosquitos with Inventive WP Formulations
Glazed tiles hâve been treated with the WP 10 formulations as described in example 9 based on 4-[(5S)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-l,2-oxazol-3yl]-N-[(4R)-2-ethyl-3-oxo-l,2-oxazolidin-4-yl]-2-methylbenzamide as described in 5 Example 4 and then stored at ambient conditions. In contact bioassays it has been shown, that the insectieidal effect of the treated surface remains stable after a period of 8 weeks. The contact bioassays hâve been conducted as outlined in example 9.
The results are shown in table 9 (as control the active ingrédient was dissolved in acetone and sprayed on the tile forming crystalline residues as can be seen for SC).
Table 9:
| Test insects: | ||||
| Mortality [%] Aedes Aegypti | Mortality [%] Culex quinque fasciatus | Mortality [%] Anopheles funestus | ||
| Formulation | mg a.i. / m2 | 24h | 24h | 24h |
| WP 10 1 day (examples 9 and 4) | 20 | 100 | 100 | 100 |
| 4 | 100 | 95 | 100 | |
| 0.8 | 85 | 80 | 60 |
| WP 10 1 month (examples 9 and 4) | 20 | 100 | 100 | 100 |
| 4 | 100 | 100 | 100 | |
| 0.8 | 95 | 100 | 70 | |
| WP 10 8 week (examples 9 and 4) | 20 | 100 | 100 | 100 |
| 4 | 100 | 100 | 100 | |
| 0.8 | 95 | 85 | 95 | |
| Reference crystalline spray 1 day (examples 9 and 4) | 20 | 100 | 100 | 90 |
| 4 | 89 | 88 | 30 | |
| 0.8 | 0 | 25 | 0 | |
| Control | 0 | 0 | 0 |
13. Biological performance of known SC Formulations with Deltamethrin and “Controlled Release” Formulations with Deltamethrin in Contact Bioassay against Mosquitos.
Similarly as outlined in example 9 a contact bioassay was conducted with the “controlled release” Deltamethrin SC 2.5 wax formulation and the conventional SC 200 formulation both prepared as described in example 6. The results are shown in table 10 (The control was the same as in example 7).
Table 10:
| Test insects: Anopheles funestus (Malaria mosquito) | ||
| Mortality [%] | ||
| Formulation | mg a.i. / m2 | 24h |
| Deltamethrin SC 2.5 (example 6) | 4 | 75 |
| Deltamethrin SC 200 (example 6) | 4 | 85 |
-32The results in table 10 show that “controlled release” formulations - in general - are not suitable to achieve optimal results in regard to contact and initial biological efficacy.
Claims (16)
- Claims:1. An insecticidal active ingrédient - matrix particles with a particle size d50 of 0.1 to 75 microns comprisinga) at least one insecticidal active ingrédient selected from the group consisting of isoxazolines, meta-diamides, arylpyrazolheteroaiylamides and arylpyrazolarylamides, wherein the at least one insecticidal active ingrédient is distributed inb) a matrix material comprising polymerized monomer units selected from the group of C7 to C12 unsaturated aromatic hydrocarbons.
- 2. An insecticidal active ingrédient - matrix material particle with a particle size d50 of 0.1 to 75 microns comprisinga) at least one insecticidal active ingrédient selected from the group consisting of isoxazolines, meta-diamides, arylpyrazolheteroarylamides and arylpyrazolarylamides, wherein the at least one insecticidal active ingrédient is distributed inb) a matrix material, characterized in that the insecticidal active ingrédient - matrix material particle does not exhibit a melting peak of the active ingrédient when measured in a second heating cycle after heating to a température of at least 20 °C above the melting point of the at least one insecticidal active ingrédient at a steady heating rate using Differential Scanning Calorimetry.
- 3. An insecticidal active ingrédient - matrix material particle according to claim 2, characterized in that in the first heating cycle of a Differential Scanning Calorimetry the at least one insecticidal active ingrédient and the matrix material are heated to a température of at least 20 °C above the melting point of the at least one insecticidal active ingrédient at a steady heating rate.
- 4. An insecticidal active ingrédient - matrix material particle according to claim 3, further characterized in that the maximal heating température of the first heating cycle is retained for a period of at least 10 minutes.
- 5. An insecticidal active ingrédient - matrix material particle according to one of the daims 3 to 4, further characterized in that the at least one insecticidal active ingrédient and the matrix material are cooled down to a température of between 0°C to 40°C between the first and second heating cycle at a steady cooling rate.
- 6. An insecticidal active ingrédient - matrix material particle according to one of the daims 1 to 5, characterized in that the weight ratio between the at least one insecticidal active ingrédient and the matrix material is from 1:99 to 1:1.
- 7. An insecticidal active ingrédient - matrix material particle according to one of the daims 1 to 6, characterized in that the at least one insecticidal active ingrédient is selected from the group consisting of 2-chloro-N-cyclopropyl-5-{l-[2,6-dichloro-4-(l,l,l,2,3,3,3heptafluoropropan-2-yl)phenyl]-lH-pyrazol-4-yl}-N-methylnicotinamide, Broflanilide and 4-[(5S)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydiO-l,2-oxazol3 -yl] -N- [(4R)-2-ethyl -3 -oxo-1,2-oxazolidin-4-yl] -2-methylbenzamide.
- 8. An insecticidal active ingrédient - matrix particle according to one of the daims 1 to 7, characterized in that molecular weigth of the matrix material is between 1 to 1000 kDa.
- 9. An insecticidal composition with an insecticidal active ingrédient - matrix material particle according to one of the daims 1 to 8, wherein the insecticidal composition comprisesa) an insecticidal active ingrédient - matrix material particle according to one of the daims 1 to 8,b) one or more surfactant(s), andc) a liquid phase and/or fïllers.
- 10. An insecticidal composition with an insecticidal active ingrédient - matrix material particle according to one of the daims 1 to 8, wherein the insecticidal composition comprisesa) an insecticidal active ingrédient - matrix material particle according to one of the daims 1 to 8,b) one or more surfactant(s),c) further adjuvants selected from the group of anti-freeze agents, anti-foam agents, preservatives, anti-oxidants, thickeners, colourants and binders, andd) a liquid phase and/or fillers.
- 11. An insecticidal composition according to claim 9, wherein the insecticidal composition comprisesa) from 1 to 70% by weight of insecticidal active ingrédient - matrix material particles according to one of the claims 1 to 8,b) from 1 to 25 % of one or more surfactant(s), andc) liquid phase and/or fillers which in any case add up to 100% per weight of the total insecticidal composition.
- 12. An insecticidal composition according to claim 10, wherein the insecticidal composition comprisesa) from 1 to 70% by weight of insecticidal active ingrédient - matrix material particles according to one of the claims 1 to 8,b) from 1 to 25 % of one or more surfactant(s),c) from 0 to 25 % by weight of adjuvants selected from the group of anti-freeze agents, anti-foam agents, preservatives, anti-oxidants, thickeners, colourants and binders, andd) liquid phase and/or fillers which in any case add up to 100% per weight of the total insecticidal composition.
- 13. An insecticidal composition according to one of the claims 9 to 12, wherein the insecticidal composition is in the form of a suspension concentrate (SC), water-dispersable granule (WG) or wettable powder (WP) or a spray solution thereof.
- 14. Use of an insecticidal active ingrédient - matrix material particle according to one of the claims 1 to 8 or an insecticidal composition according to one of the claims 9 to 13 to control pests.
- 15. Method to control pests with an insecticidal active ingrédient - matrix material particle according to one of the claims 1 to 8 or an insecticidal composition according to one of the claims 9 to 13.
- 16. A method to identify a useful matrix material for an insecticidal composition with Differential Scanning Calorimetry as follows:a) at least one insecticidal active ingrédient selected from the group consisting of isoxazolines, meta-diamides, arylpyrazolheteroarylamides and 5 arylpyrazolarylamides and a matrix material to be tested are heated to a température of at least 20 °C above the melting point of the at least one insecticidal active ingrédient at a steady heating rate in a first heating cycle of the Differential Scanning Calorimetry,b) the maximal heating température of the first heating cycle is retained for a period of 10 at least 10 minutes,c) the température is then cooled down to a température of between 0°C to 40°C,d) in a second heating cycle step, the température is raised to a température of at least 20 °C above the melting point of the at least one insecticidal active ingrédient at a steady heating rate, and15 e) a useful matrix material is identified in case that the insecticidal active ingrédient matrix material combination does not exhibit a melting peak when measured in the second heating cycle of the Differential Scanning Calorimetry.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP18213622.6 | 2018-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA20240A true OA20240A (en) | 2022-03-18 |
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