JP2000508291A - Emulsifying composition for controlling insects - Google Patents

Abstract

  (57) [Summary] An emulsifiable composition for controlling insects, especially termites, comprising a 1-substituted phenyl-3-CN-pyrazole as active ingredient and a weakly polar solvent and an emulsifier and optionally some further additives or solvents. These compositions suppress the formation of crystals.

Description

DETAILED DESCRIPTION OF THE INVENTION emulsifiable composition the invention for insects control is emulsifiable composition for insects control and methods of using thereof. The emulsifiable compositions of the present invention are derived from 1-substituted phenylpyrazole pesticides, and they do not promote crystal formation. 1-Substituted phenylpyrazole insecticides can tend to cause some crystallization in their compositions during storage or use. When using such compounds for various applications, there may be crystallization or recrystallization problems that hinder proper and easy application. This includes spray application through nozzles (nozzles can be blocked), dilution in tanks (active ingredients can thus crystallize and fall to the bottom of the tanks), application to animal hair ( The quality of the hair can be impaired by the deposition of crystals thereon), which can occur in a number of completely different practical applications. A very important requirement for pets is that they have good quality hair that is satisfactory when touched or caressed. Furthermore, specialists in controlling insects, especially termites, often prepare diluted pesticide solutions one day before application and utilize the remaining solution at a later date. These liquors contain crystalline active ingredients and therefore have poor emulsifiability and tend to crystallize in a few hours after the preparation of the emulsion for spraying, resulting in large amounts of useless liquors or Causes clogging of pump nozzles used for foam applications. In the particular context of methods for controlling insects, especially termites, these methods can generally be divided into two main groups. One side is a wood treatment in which the wood part of the house is subjected to pesticide treatment, and the other side is called a soil treatment in which liquid pesticide is sprayed onto the underfloor area of the house. In consideration of the health of workers when applied in a limited space under the floor, the application of flowable formulations in which the active ingredient is suspended in water is becoming predominant. However, such dilution of water has a tendency to form crystals. Conventional flowable formulations are not satisfactory. Japanese Patent Publication No. 2-7282 proposes to prevent crystallization of some active ingredients that are not 1-substituted phenylpyrazole insecticides. Japanese Patent Application No. 50-69230 describes a liquid herbicidal composition containing as active ingredients a dinitroaniline herbicide and an N-allyl-N'-alkoxyurea herbicide. It also discloses the use of a solvent consisting of an emulsifier and a cycloaliphatic ketone to give the composition physical stability under the conditions of transport, storage and end use. It is an object of the present invention to provide an improved emulsifiable composition which reduces the odor of the solvent and / or prevents the crystallization of the 1-substituted phenylpyrazole pesticides upon dilution and / or is generally superior to conventional flowable formulations. To provide. The emulsifiable composition according to the invention comprises an insecticidal active ingredient which is a compound of the formula (I), and one or more weakly polar solvents, and an emulsifier, and optionally one or more further solvents. . Formula (I) for compounds used as active ingredients in the present ^{invention, 1- [4-R 1 -2,6-} (R 2) p - phenyl] -3-cyano -4- [R ⁴ -S ( O) _n ] -5-R ⁵ -pyrazole (I) wherein R ¹ is halogen, lower haloalkyl, lower haloalkoxy or SF ₅ (lower is an integer of 1-4, preferably 1). R ² is halogen, wherein the various R ² are the same or different; R ⁴ is halogen, lower alkyl or haloalkyl; R ⁵ is halogen, lower alkyl or amino; n Is 0 or 1 or 2, and p is 0 or 1 or 2, and is preferably 2. ]. A halo before the name of a radical means that the radical can be replaced by one or more halogen atoms. Preferred compounds of the formula (I) are compound 5-amino-3-cyano-1- (2,6-dichloro-4-trifluoromethylphenyl) -4-trifluoromethylsulfinylpyrazole (hereinafter referred to as compound (A) ). The compositions of the present invention are effective in treating a number of insects, especially termites, fleas, or arachnids such as mites, and more generally to dogs, cats and other pets. It is useful for treating insects, as well as other insects listed in European Patent Application No. 295117, which is incorporated herein by reference. The compounds of the formula (I) used in the emulsifiable compositions for controlling insects, in particular termites, according to the invention are known and are described in EP-A-295117 and International Patent Applications WO 93/6089 and 94/21606. Have been. They are effective for controlling arthropods, plant nematodes, protozoan pests, insects, especially termites, farm pests and the like. Weakly polar solvents that can be used in the present invention are generally those that have a positive, preferably higher than 1, dipole moment (in Debye units) and a solubility in water (at 20 ° C.) of less than 10%. These weakly polar solvents are preferably selected from among cyclic amides and glycolic ether solvents. Examples of cyclic amides that can be used are N-octyl-2-pyrrolidone, N-dodecyl-2-pyrrolidone and N-dodecyl-caprolactam. Examples of glycol ether type weak polar solvents include ethylene glycol monophenyl ether, ethylene glycol monohexyl ether, ethylene glycol mono-2-ethylhexyl ether, ethylene glycol dibutyl ether, diethylene glycol dibutyl ether, propylene glycol monophenyl ether, and dipropylene glycol. Monopropyl ether, ethylene glycol monobenzyl ether and the like. A preferred glycol solvent is diethylene glycol mono-2-ethylhexyl ether. The emulsifiers that can be used are preferably those selected from one or more nonionic or anionic emulsifiers. Examples of nonionic emulsifiers that may be mentioned include polyoxyalkyl ethers, polyoxyethylene alkyl phenyl ethers, polyoxyethylene alkyl ethers, polyethylene glycol fatty acid esters, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbit fatty acids. Contains esters (polyoxyethylenesorbit fatty ester), polyoxyethylene polyoxypropylene alkyl ether, and polyoxyethylene (castor oil) ether. Examples of anionic emulsifiers that may be mentioned include alkyl sulfates, polyoxyethylene alkyl ether sulfates, sulfosuccinates, taurine derivatives, sarcosine derivatives, alkylbenzene sulfonates and the like. Preferred emulsifiers are mixtures comprising polyoxyethylene styryl phenyl ether and calcium alkylbenzene sulphonate (emulsifier a ) and mixtures comprising polyoxyethylene (castor oil) ether and calcium alkyl benzene sulphonate (emulsifier b ). Aromatic solvents may generally be used in the compositions of the present invention to improve the solubility and / or permeability of the active ingredient. These aromatic solvents are preferably selected from those which are in the liquid state at room temperature (ie, liquid at room temperature or below 30 ° C.) and have a boiling point above 200 ° C. They may more particularly be selected from petroleum fractions, catalytic cracking oil fractions or synthetic oils and the like. Examples which may be mentioned are: mono- or polyalkylbenzenes such as alkylbenzene or trimethylbenzene; naphthalenes such as methylnaphthalene, dimethylnaphthalene, dimethylmonopropylnaphthalene, dimethyldipropylnaphthalene or phenylxylylnaphthalene; 1-phenyl-1 -Alkyldiphenylalkanes such as xylylethane or alkyldiphenylethane; indene derivatives; dibenzyl ethers; diester phthalates. 1-phenyl-1-xylylethane, dibenzyl ethers, dimethylmonopropylnaphthalene, and dimethyldipropylnaphthalene are preferred. If desired, the compositions of the present invention may contain more polar solvents. Polar solvents that are not weakly polar solvents generally have a dipole moment in positive, preferably greater than 1, units are in Debye, while having a solubility in water greater than 10%. Such polar solvents include cyclic amides or lactones such as N-methyl-2-pyrrolidone, N-cyclohexyl-2-pyrrolidone, caprolactone and butyrolactone, and glycol ethers such as tripropylene glycol monomethyl ether and diethylene glycol dimethyl ether. including. While the proportions of each component of the compositions of the present invention may vary over a wide range of values, more preferred advantageous compositions are 1-10% of one or more pesticidally active ingredients, and / or 3-90. % More preferably 5 to 30% of one or more weakly polar solvents, and / or 5 to 40% of one or more emulsifiers, and / or optionally 0 to 90% of one or more further Further aromatic solvents; the proportion of such solvents in the composition according to the invention is advantageously greater than 50%; and / or optionally from 0 to 20% as defined herein above. It contains one or more more polar solvents (these proportions being given as weight percentages being the same as parts by weight per 100 parts by weight of the composition). The emulsifiable composition of the present invention may also contain other additives according to the general knowledge of the agricultural pharmaceutical manufacturing field. For certain applications, in particular for controlling termites and / or treating underfloor homes, some specific additives may be added, such as foaming or foam stabilizers. The emulsifiable composition of the present invention can be manufactured by any of the conventional methods suitable for emulsions. The present invention also relates to a method for controlling termites, wherein an effective amount of a composition as defined above is applied to places where such pests are or are expected to infest. Application can be by any suitable means, such as spraying, painting, impregnating. The compositions of the present invention, when used against termites, can be used in soil or underfloor soils to protect wood, such as trees, fences and railroad sleepers, or buildings, such as homes, warehouses, and industrial plants. It can be applied not only for treating surfaces or interiors, but also in timber products such as plywood and furniture, wood products such as particle board and half board, and vinyl products such as coated wires and sheets. The compositions of the present invention can also be used in any other type of application, including pesticide applications in crop growing areas and veterinary use. The present invention further provides a method of controlling fleas or mites or insects from animals such as dogs and cats, comprising administering an effective amount of a composition as described above to or against such pests. It is intended for the method of application to the animal, wherein the application dose of the active ingredient is preferably between 0.1 and 100 mg, preferably between 2 and 20 mg per kilogram of body weight of the animal. When the composition for soil treatment according to the invention is used for controlling insects, for example for controlling termites, in particular for soil treatment and / or for treating underfloor soil, the amount of active ingredient per square meter 0.01 mg to 15 mg, preferably 0.1 mg It can be in the range between 1 mg and 5 mg. The present invention is illustrated by the following Examples, Comparative Examples and Experimental Examples, but is not limited to those details. Unless indicated otherwise, parts are by weight. Example 1 5 parts of compound (A), 15 parts of N-octyl-2-pyrrolidone, 10 parts of emulsifier a (Solpol 355X available from Toho Kagaku Kogyo KK) and 70 parts of 1 -Phenyl-1-xylylethane was homogeneously dissolved to obtain an emulsifiable composition of the present invention. Examples 2 to 29 In each of these examples, in a manner analogous to Example 1, by the corresponding formula shown in Table 1 for Examples 1 to 15, and for Examples 16 to 29 The emulsifiable composition according to the invention was prepared according to the corresponding formulation shown in Table 2. Comparative Example 1 An emulsifiable composition was prepared by mixing and dissolving 2 parts of compound (A), 5 parts of N-methyl-2-pyrrolidone, 15 parts of the emulsifier, and 78 parts of 1-phenyl-1-xylylethane. Obtained. Comparative Example 2 2 parts of compound (A), 5 parts of propylene glycol, 5 parts of dispersant (polyoxyethylene styryl phenyl ether; Penelol SP2440 available from Matsumoto Yushi Seiyaku KK), 1 part Of a wetting agent (sodium dioctyl sulfosuccinate), 0.25 parts of xanthan gum, 0.5 parts of a silicone antifoam and 86.25 parts of water were homogeneously mixed to give a suspension composition. Physical Efficacy: Experimental Example 1 : Crystallization Test in Diluted Liquid A 100 ml bead was charged with 100 ml of 3 ° hard water, into which 2.5 g of the emulsion prepared according to each of the above Examples and Comparative Examples The acidic composition was added, and then sufficiently stirred and mixed. After standing at 5 ° C. for 24 hours, the obtained diluted solution was passed through a sieve having an opening of 45 μm, and the amount of crystals remaining on the sieve was evaluated by visual observation. No crystal or crystallization was observed in any of Examples 1 to 29. On the other hand, in Comparative Example 1, a large amount of crystals and crystallization were observed. Biological efficacy: Experimental example 2 : Control test for termites Two glass cylindrical tubes (about 5 cm in inner diameter, about 12 cm in height) were placed at a distance of about 2 cm from the bottom of these cylindrical tubes. (5 cm, height about 10 cm). About 60 g of untreated soil adjusted to 25% moisture was introduced into one of the glass cylindrical tubes, and about 0.29 g of filter paper (5.5 mm in diameter) was introduced into the other tube. . A test solution diluted with 0.6 g of water (2.4 g of the composition of Example 1 and Comparative Example 2) was prepared by passing 2.4 g of untreated soil dried at 60 ° C. through a 200-mesh sieve (75-micron opening size). ) And kept at room temperature for 3 weeks. The resulting mixture was then introduced into the central area of the glass tube, and then the device was assembled. 220 termites ( Coptotermes formosanus , 200 termites and 20 soldiers) were introduced into the glass cylindrical tube containing the untreated soil. The apparatus was then left at 28 ° C. and 70% or more humidity. Twenty-one days after the introduction of the insect, the perforation distance (cm) was measured. These results are shown in Table 3.

────────────────────────────────────────────────── ─── Continuation of front page    (81) Designated countries EP (AT, BE, CH, DE, DK, ES, FR, GB, GR, IE, IT, LU, M C, NL, PT, SE), OA (BF, BJ, CF, CG , CI, CM, GA, GN, ML, MR, NE, SN, TD, TG), AP (KE, LS, MW, SD, SZ, U G), AL, AM, AU, BB, BG, BR, BY, C A, CN, CZ, EE, FI, GE, HU, IS, JP , KG, KP, KR, KZ, LK, LR, LS, LT, LV, MD, MG, MK, MN, MX, NO, NZ, P L, RO, RU, SG, SI, SK, TJ, TM, TT , UA, US, UZ, VN

Claims (1)

[Claims] 1. An emulsifiable composition for controlling insects, comprising an insecticidal active ingredient which is a compound of formula (I), and one or more weakly polar solvents, and an emulsifier, and optionally one or more further ingredients. the solvent contains, Thus expression of the compound of formula (I) is ^{1- [4-R 1 -2,6- (} R 2) p - phenyl] -3-cyano -4- [R ⁴ -S ( O) _n ] -5-R ⁵ -pyrazole (I) wherein R ¹ is halogen, lower haloalkyl, lower haloalkoxy or SF ₅ (lower is an integer of 1 to 4, preferably 1) R ² is halogen, wherein the various R ² are the same or different; R ⁴ is halogen, lower alkyl or haloalkyl; R ⁵ is halogen, lower alkyl or amino; n is 0 or 1 or 2, p is 0 Or 1 or 2, preferably 2. ] The composition described above. 2. 2. The compound according to claim 1, wherein the compound of formula (I) is 5-amino-3-cyano-1- (2,6-dichloro-4-trifluoromethylphenyl) -4-trifluoromethylsulfinylpyrazole. Composition. 3. 3. The composition according to claim 1 or 2, wherein the weakly polar solvent comprises a solvent having a positive dipole moment, preferably greater than 1, and a solubility in water of less than 10%. 4. The method according to any one of claims 1 to 3, wherein the weakly polar solvent comprises N-octyl-2-pyrrolidone or N-dodecyl-2-pyrrolidone or N-dodecyl-caprolactam or glycol ether. Composition. 5. The composition according to any one of claims 1 to 4, comprising a nonionic or anionic emulsifier. 6. The composition according to any one of claims 1 to 5, wherein the aromatic solvent comprises a solvent which is in a liquid state at a temperature lower than 30 ° C and / or has a boiling point of 200 ° C or higher. 7. The composition according to any one of claims 1 to 6, further comprising a polar solvent having a positive dipole moment higher than 1 and a solubility in water higher than 10%. 8. 8. The method according to claim 1, wherein the polar solvent is N-methyl-2-pyrrolidone or N-cyclohexyl-2-pyrrolidone or caprolactone or butyrolactone or tripropylene glycol monomethyl ether or diethylene glycol dimethyl ether. A composition as described. 9. 1 to 10% of one or more pesticidally active ingredients, and / or 3 to 90% more preferably 5 to 30% of one or more weakly polar solvents, and / or 5 to 40% of one Or more emulsifiers, and / or optionally 0-90% of one or more aromatic solvents; the proportion of such solvents in the composition according to the invention is generally greater than 50%; And / or optionally containing 0-20% of one or more more polar solvents as hereinbefore defined. A composition according to claim 1. 10. A method for controlling arachnids or insects, especially termites, wherein an effective amount of the composition of any one of claims 1 to 9 is infested or infested by such pests. and was applied to the location to be expected, the Thus applied dose of the active ingredient is preferably 0.01~15mg / m ² range, more preferably the method is in the range of 0.1~ 5mg / m ^2. 11. A method for controlling fleas, mites or insects from animals, preferably dogs and cats, comprising administering an effective amount of the composition according to any one of claims 1 to 9 to such a pest. The above method wherein the application is to the animal that is or is expected to be infested, the application dose of the active ingredient preferably being in the range of 0.1-100 mg, preferably 2-20 mg per kilogram of body weight of the animal. .