MXPA97003588A

MXPA97003588A - Emulsifiable composition for insec control

Info

Publication number: MXPA97003588A
Application number: MXPA/A/1997/003588A
Authority: MX
Inventors: Mizutani Takaaki; Ikeda Michihiko; Kodama Hiroshi; Shibayama Masakazu
Original assignee: Ikeda Michihiko; Kodama Hiroshi; Mizutani Takaaki; Rhonepoulenc Agrochimie; Shibayama Masakazu
Priority date: 1994-11-30
Filing date: 1997-05-15
Publication date: 1998-07-03

Abstract

The present invention relates to an emulsifiable composition for the control of insects, especially termites, which comprises as active ingredients a 1-substituted phenyl-3-CN-pyrazole, a weakly polar solvent, an emulsifying agent and optionally some additional additives or solvents . These compositions prevent the formation of glass

Description

EMULSIFIABLE COMPOSITION FOR INSECT CONTROL DESCRIPTION OF THE INVENTION The present invention relates to an emulsifiable cable composition for the control of insects and to a method for using same. The emulsifiable compositions of the present invention are derived from 1-substituted phenyl-1-pyrazole insecticides and do not favor crystal formation. The 1-substituted phenylpyrazole insecticides may be prone to generate some crystallizations in the composition during storage or use. When such compounds are used for various applications, there may be problems by crystallization or recrystallization, which prevents an appropriate and easy application. This could happen in a very different number of practical applications, such as spraying applications through a nozzle, which can be plugged; dilution in a tank, where the active ingredient can crystallize and fall to the bottom of the tank; applications to animal hair n where hair quality can be damaged by crystal deposits. For pets, a very important requirement is that they have a high quality of hair, which is pleasant and pleasant when touched or caressed. REF: 24371 In addition, it is common for specialists in the control of insects, especially termites, to prepare a diluted pesticide liquid the day before the application and use the remaining liquid the next day. These liquids, since they contain crystalline active ingredients. they are poorly emulsified and are prone to crystallize over a period of several hours after preparing the spray emulsion, resulting in a large volume of waste liquid or causing the nozzles used for foam application to be clogged. In the particular situation of insect control methods, especially of termites, these methods can generally be divided into two main groups. On the one hand. there is the treatment of wood, according to which the wooden parts of a house are subjected to pesticide treatment; and on the other hand there is the so-called soil treatment, according to which a liquid pesticide is sprayed in the area under the floor of a house. The application of a fluid formulation in which the active ingredient is suspended in water, is becoming predominant, in consideration of the health of the workers, who apply it within the limited space under the floor. However, such dilution of water has a tendency to generate crystals. Conventional fluid formulations are not satisfactory. Japanese Patent Publication No. 2-7282 has proposed to prevent the crystallization of some active ingredients which are not 1-substituted phenylazole insecticides. Japanese Patent Application No. 50-69230, has described a liquid herbicidal composition which contains as active ingredients a dinitroanilic acid herbicide and an N-allyl-N'-alkoxyurea herbicide. It also describes the use of an emulsifying agent and a solvent consisting of an alicyclic ketone, in order to give the composition physical stability under the conditions of transportation, storage and end use. It is an object of the present invention to provide improved emulsifiable compositions that reduce the odor of solvent or solvents and / or prevent crystallization of 1-substituted phenylazole insecticides when diluted and / or which are generally superior to conventional fluid formulations. The emulsifiable compositions of the present invention contain: an insecticidally active amount which is a compound of the formula (I), and one or more weakly polar solvents, and an emulsifying agent. and optionally one or more additional solvents. Formula (I) for the compounds used as active ingredients in the present invention is the following: 1 _2 4 5 l- [4-R 2, o- (R) p-phenyl] -3-cyano? L- [R -5 (0) J5-R-pyrazole (I) wherein 1 R is a halogen, a lower haloaikyl radical. lower haloalkoxy or SF-. (an integer from 1 to 4, preferably 1) being considered as lower, R 2 is a halogen, the various R 2 being identical or different, R is a halogen, a lower alkyl or haloalkyl radical, R is a halogen, a lower alkyl or amino radical, n is 0 or 1 or 2; p is 0 or 1 or 2, preferably 2. The prefix "halo" in the name of a radical, means that this radical may be substituted by one or more halogen atoms. A preferred compound of Formula (I) is the compound 5-amino-3-cyano-1- (2,6-dichloro-4-trifluoromethyl lfeni 1) -4-trifluorome i lsulfini 1-pyrazole, hereinafter referred to as compound (A). The compositions of the present invention are useful for the treatment of many insects, especially termites, fleas or arachnids such as ticks and more generally insects in dogs or cats and other companion animals, as well as other insects such as those cited in the Application. European Patent No. 295117, which is incorporated herein by reference. The compounds of the Formula (I) used in the emulsifiable composition for the control of insects, especially termites, of the present invention are known and described in European Patent Application No. 295117, as well as in Patent applications. International W093 / 6089 and 94/21606. These are effective for the control of arthropods, plant nematodes, protozoan pests, insects, especially termites, farm pests and the like. The weak polar solvents that can be used in the invention are generally those that have a positive dipole moment, preferably greater than 1 (the unit is debye) and a solubility in water (at 20 ° C) less than 10 *. These weak polar solvents are preferably selected from the cyclic amides and the glycol ether solvents. Examples of the cyclic amides that can be used are N-octi 1-2-pyrrole idone, N-dodecyl-2-pyrrolidone and N-dodecyl-caprolactam.

Examples of the solvent or weakly polar solvents of the glycol ether type are: ethylene glycol phenyl ether, ethylene glycol monoethyl ether, eti lengl? Colmono-2-et? lhexi léter, eti lengl icoldibut i léter, dieti lengl icoldibuti lter, prop i lengl icolmonofeni léter. dipropa lengl ic lmonopropí léter, eti lengl icol onobencí léter and the like. The preferred glycol solvent is diethylene glycol-2- t? lhexi léter. The emulsifying agents that can be used are preferably one or more of the group consisting of nonionic or anionic emulsifying agents. Examples of the nonionic agents and ulsifiers that may be mentioned include: polyoxyalkylene ether. pol ioxiet fills lqui lfeni léter. polyexieti lenalqui lter, fatty ester of polyethylene glycol, fatty ester of sorbitan, fatty ester of poloxiet and linoorbitan, fatty ester of polioxyti lensorbitan. pol ioxieti lenpol ioxi-propí lenalqui léter, pol ioxieti len (ace? te de pc? no) ether. Examples of the anionic emulsifying agents that may be mentioned include the alkyl sulfates, polyolieti lenalkyl ether sulfates, sulfosuccinates, taurine derivatives, sarcosine derivatives, alkyiumbencenesulfonates and the like. Preferred agents and ulsifiers are mixtures comprising polyoxyethylenaline lphenether and calcium alkylbenzenesulfonate (emulsifying agent a) and mixtures comprising polyoxyethylene (castor oil) ether and calcium alkybenzenesulfonate (emulsifying agent b). Aromatic solvents may be used in the compositions of the present invention, generally to improve the solubility and / or penetration of the active ingredient. This solvent or aromatic solvents are preferably selected from the group consisting of those which are in the liquid state at normal temperature (i.e., which are liquid at room temperature or at a temperature below 30 * C) and which have a boiling point of at least 200 * C These can be selected more particularly from the petroleu fraction, from the oil fraction obtained by crack or synthetic oil catalysis and the like. Examples that may be mentioned include: mono- or poly-alkyl-benzenes, such as alkyl-benzene or trimethyl-benzene; naphthalenes such as methylnaphthalene, dimethyl 1naphtha. dimethyl lmonopropyl lnaphthalene, dimethyl l-dipropylnaphthalene or phenylxy lnaphthalene; ali Idifeni lalcanos; such as 1-pheny1-xi-li-letan or alkyldifeni-letan; indene derivatives; dibenzyl ethers; diester phthalates and the like. Preference is given to 1-pheny1-xyloxylatane, dibenzyl ethers, dimethyl Imonopropyl 1 naphtha, dimethylpropyl 1-naphthalene. If necessary, the composition of the present invention may contain a further polar solvent. Polar solvents that are not weak polar solvents are usually those that have a positive dipole moment, preferably greater than 1 (the unit is debye). while they have a solubility in water greater than 10%. Such polar solvents include cyclic amides or lactones, such as N-methyl-2-pyrrolidone. N-cyclohexy 1-2-pyrrole idone, caprolactone, butyrolactone; and glycol ethers such as tripropylen glycol onomethyl ether. dieti lengl icoldimeti léter.

Although the proportions of each component of the compositions of the present invention may vary over a wide range of values, the advantageous compositions that are most preferred are those containing (proportions being given in the form of percent by weight, which is equal to the parts by weight per 100 parts by weight of the composition): from 1 to 10% of the insecticidally active ingredient or ingredients and / or from 3 to 90% of the weakly polar solvent or solvents, more preferably from 5 to 30 % and / or from 5 to 40% of the emulsifying agent or agents, and / or optionally from 0 to 90% of an additional aromatic solvent or solvents; the proportion of this solvent or solvents in the composition of the present invention is advantageously greater than 50%; and / or optionally from 0 to 20% of an additional polar solvent or solvents such as those defined above. The emulsifiable compositions of the present invention may also contain other additives according to the general knowledge of the art of agrochemical formulations. For certain applications, especially for the control of termites and / or the treatment under the floor of houses. you can add some specific additives such as foaming agents or a foam stabilizer. The emulsifiable compositions of the present invention can be prepared by any conventional process suitable for emulsifiable concentrates. The present invention also relates to a method of controlling termites, by means of which an effective amount of a composition such as those described above is applied to the site that is infested or is expected to be infested by said pests. The - in ¬ Applications can be made according to any suitable means, such as by spraying, coating, impregnation. The compositions of the present invention, when used against termites, can be applied not only for the treatment of the surface or the interior of the floor or under the floor of houses, but also for protecting wood such as trees, fences and sleepers from railroad, or constructions such as houses, warehouses and industrial plants, as well as for timber products such as multi-laminar wood and furniture, wood products such as particle boards and half tables, and vinyl products such as coated wires and sheets. The compositions of the present invention can also be used in any other type of applications, including agrochemical applications for cultivable areas and for veterinary uses. The present invention further relates to a method of controlling fleas or ticks or insects of animals such as dogs and cats, wherein an effective amount of a composition such as that described above is applied to the animal that is infested or is expected to be infected. infested by these pests. wherein the applied dose of the active ingredient is preferably 0.01 to 100 mg, preferably 2 to 20 mg per kilogram of animal body weight. - li ¬ when the soil treatment compositions of the present invention are used for the control of insects, for example for the control of termites, especially for the control of soils and for the treatment under the floor of houses, the effective amount of the ingredient may be in the range of 0.01 to 15.0 mg / m 2 of preference between 0.1 to 5.0 mg / 2. The present invention is illustrated by the following examples, comparative examples and experimental examples, but is not limited to the details thereof. Unless otherwise specified, the parts are given by weight. Example 1 5 parts of the compound (A), 15 parts of N-octi 1-2-pyrrole idone, 10 parts of the emulsifying agent a (Solpol 355X available in Toho Kagaku Kogyo KK) and 70 parts of 1-phenylein 1 were homogeneously dissolved. -1-xi 1 i, to obtain an emulsifiable composition according to the present invention. Examples 2 to 29 In each of these Examples, an emulsifiable composition according to the present invention was prepared in a manner similar to Example 1. according to the corresponding formulations shown in Table 1 for Examples 1 to 15 and according to Table 2 for Examples 16 to 29. Comparative example 1 2 parts of the compound (A), 5 parts of N-met i 1-2-pyrrole idone, 15 parts of the emulsifying agent and 78 parts of 1-pheny1-1 were mixed and dissolved. -xi 1 and litanol, to obtain an emulsifiable composition. Comparative Example 2 2 parts of compound (A) were homogeneously mixed. 5 parts of propylene glycol, 5 parts of the dispersing agent (polyoxyethyiinethanol lphenylether, Penerol SP2440, available from Matsumoto Yushi Seiyaku K.K.). 1 part of wetting agent (dioctyl sodium phosuccinate), 0.25 parts of xanthan gum, 0.5 parts of silicon antifoaming agent and 86.25 parts of water, to obtain a suspension composition. Physical Efficacy: Experimental Example 1: Crystallization Test in Diluted Liquid To a 100 ml precipitation beaker. 100 ml of hard water 3 * were introduced. 2.5 g of an emulsifiable composition prepared according to each of the above Comparative Examples and Examples were added and then stirred and mixed well. After allowing to stand at 5'C for 24 h. the obtained diluted liquid was passed through a sieve of 45 micras of aperture, then the amount of crystals remaining was evaluated by visual observation. No crystals or crystallization were observed in any of Examples 1 to 29. On the contrary. large amounts of crystals and crystallization were observed in Comparative Example 1. Biological Efficacy: Experimental Example 2: Termite Control Test An experimental system comprising two cylindrical glass tubes (approximately 5 cm in internal diameter) was used., approximately 12 cm high), which were connected to a glass tube (approximately 1.5 cm in internal diameter, approximately 10 cm in height) at a distance of approximately 2 cm from the bottom of the cylindrical tubes. In one of the cylindrical glass tubes, approximately 60 g of an untreated soil whose moisture content had been controlled to have a value of 25% were introduced and in the other tube approximately 0.29 g of a filter paper (5.5 mm) was introduced. diameter) . 2.4 g of the untreated soil was passed through a 200 mesh screen (opening size 75 microns) and dried at 60 * C; it was mixed with 0.6 g of the liquid to be tested (compositions of Example 1 and Comparative Example 2) diluted with water and kept at room temperature for 3 weeks. Later. The resulting mixture was introduced into the central region of the glass tube and then the system was assembled. Table 1 Table 3 It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention. Having described the invention as an antecedent, what is contained in the following is claimed as property.

Claims

CLAIMS 1. An emulsifiable composition for insect control, characterized in that it contains: an insecticidally active ingredient which is a compound of Formula (I), and one or more weakly polar solvents, and an emulsifying agent, and optionally one or more additional solvents, wherein the formula of the compound of Formula (I) is 1 2 4 5 l- [4-R 2,6- (R) -p-phenylj-3-cyano-4- R -S (0 )} -5-R-pyrazole (I) wherein: R is a halogen, lower haloalkyl, lower haloalkoxy or SF_ (considering an integer from 1 to 4, preferably 1), R 2 is a halogen, the various R2 identical or different, 4 R is a halogen, lower alkyl or haloalkyl, R is a halogen, lower alkyl or amino, n is 0 or 1 or 2; p is 0 or 1 or 2, preferably 2.
2. A composition according to claim 1, characterized in that the compound of the formula (I) is 5-amino-3-cyano-1- (2,6-dichloro) -4-trif luorometi 1 feni 1) -4-tif luorome and Isulfini 1-pyrazole.
3. A composition according to any of the preceding claims. characterized in that it comprises as the weakly polar solvent a solvent having a dipole moment preferably greater than 1 and a solubility in water of less than 10%.
4. A composition according to any of the preceding claims. characterized in that it comprises as the weakly polar solvent N-octyl-2-pyrrole idone or N-dodecyl 1-2-pyrrole idone or N-dodecyl-caprolactam or a glycol ether.
5. A composition according to any of the preceding claims characterized in that it comprises a nonionic or anionic emulsifying agent.
6. A composition according to any of the preceding claims, characterized in that it comprises as an aromatic solvent a solvent that is in a liquid state at temperatures lower than 30 * C and / or that has a boiling point of at least 200"C. A composition according to any of the preceding claims, characterized in that it further comprises a polar solvent having a positive dipole moment greater than 1 and a solubility in water greater than 10% 8. A composition according to any of the preceding claims. , characterized in that the polar solvent is N-met i 1-2-pyrrole idone or N-cyclohexy-2-pyrrole idone or caproiactone or butyrolactone or tripropi lengl icolmonomethyl ether or diethyl glycol dimethyl ether. with any of the preceding claims, characterized in that it comprises from 1 to 10% of the insecticidally active ingredient or ingredients, and / or from 3 to 90% of the solvent or weakly polar solvents, (more preferably from 5 to 30%, and / or from 5 to 40% of the emulsifying agent or agents »and / or optionally from 0 to 90% of a solvent or solvents additional aromatics; the proportion of this solvent or solvents in the composition of the present invention being generally greater than 50%; and / or optionally from 0 to 20% of an additional polar solvent or solvents, such as those defined above. 10. A method of controlling arachnids or insects. especially of termites, characterized in that an effective amount of a composition according to any of the preceding claims is applied to the place that is infested or is expected to be infested by said pests, the dose of active ingredients being preferably in the range 2 from 0.01 to 15 mg / m, and more preferably in the range from 2 0.1 to 5 mg / m. 11. A method of controlling fleas or ticks or insects of animals, preferably dogs and cats, characterized in that an effective amount of a composition according to any of the preceding claims is applied to the animal that is infested or is expected to be infested by said pests, the applied dose of the active ingredients being preferably in the range of 0.1 to 100 mg, more preferably 2 to 20 mg per kilogram of animal body weight.