MXPA06009360A

MXPA06009360A - Anthranilamides, process for the production thereof, and pest controllers containing the same

Info

Publication number: MXPA06009360A
Application number: MXPA/A/2006/009360A
Authority: MX
Inventors: Masayuki Morita; Toru Koyanagi; Kenichi Nakamoto; Akihiro Hisamatsu
Original assignee: Ishihara Sangyo Kaisha Ltd
Priority date: 2004-02-18
Filing date: 2006-08-17
Publication date: 2006-12-13

Abstract

The invention provides novel anthranilamides useful as pest controllers, salts of the same, a process for the production thereof, and pest controllers containing these compounds as the active ingredient. Anthranilamides represented by the general formula (I) or salts thereof:(I) wherein R1 is halogeno, alkyl, haloalkyl, or the like;R2 and R3 are each independently halogeno, alkyl, haloalkyl, or the like;A is alkyl substituted with Y;Y is C3-4 cycloalkyl which may be substituted with at least one member selected form the group consisting of halogeno, alkyl, and haloalkyl;m is 0 to 4;n is 0 or 1;and q is 0 to 4.

Description

ANTRANILAMIDAS, PROCEDURE FOR ITS PRODUCTION AND CONTROLLERS OF PESTS THAT CONTAIN THEM TECHNICAL FIELD Patent documents 1, 2, 3 and 4, respectively, describe anthranilamide compounds having certain specific chemical structures. However, nowhere in said patent documents are disclosed compounds having alkyl substituted by C3- cycloalkyl as a substituent corresponding to A in the aforementioned formula (I) of the present invention. In addition, the patent document 5 describes anthranilamide compounds having a cyano group in the 4-position of the benzene ring. However, a cyano group is not contained in the description of R1 in the aforementioned formula (I) of the present invention, and the respective chemical structures are different. Patent Document 1: International Publication WO03 / 24222 Patent Document 2: International Publication WO03 / 15518 Patent Document 3: International Publication WO03 / 15519 Patent Document 4: International Publication WO01 / 70671 Patent Document 5: International Publication WO04 / 67528 BRIEF DESCRIPTION OF THE INVENTION Problems to solve through the invention For many years, many pesticides have been used, but many of them have several problems such as that the effects are inadequate, that their use is restricted to pests that have acquired resistance, etc. therefore, it is desirable to develop a novel pesticide substantially free of such problems, for example, a pesticide capable of controlling various pests that create problems in agricultural and horticultural fields or a pesticide that is capable of controlling parasitic pests in animals.

Means for solving the problems The present inventors have conducted several studies on anthranilamide compounds in an effort to find a superior pesticide. As a result, they found that a novel anthranilamide compound or its salt has an extremely high pesticidal effect against pests at a low dose which has achieved the present invention. Primarily, the present invention relates to an anthranilamide compound represented by the formula (I) or its salt: wherein R 1 is halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, phenoxycarbonyl which may be substituted, nitro or formyl; each of R2 and R3 which are independent of each other, is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, or cyano; A is an alkyl substituted by Y; Y is C3-4 cycloalkyl which may be substituted by at least one substituent selected from the group consisting of halogen, alkyl, and haloalkyl; m is from 0 to 4; n is from 0 to 1; and q is from 0 to 4; always when R1 is a fluorine atom, a chlorine atom, a bromine atom or methyl substituted in the 2-position of the benzene ring and the other R1 is halogen substituted in the 4-position of the benzene ring, the halogen in the position 4 is a fluorine atom or a chlorine atom; a procedure for this production; and a pesticide that contains it.

Effects of the invention The pesticide containing, as an active ingredient, a novel anthranilamide compound represented by the above formula (I), has a very high pesticidal effect against low-dose pests.

PREFERRED MODALITY OF THE INVENTION Substituents for phenoxycarbonyl which may be substituted, in R 1, may, for example, be halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyano and nitro. The number of said substituents may be one or more, and if more, the respective substituents may be the same or different. In addition, the positions for substitution for the respective substituents can be any positions. The number of substituents Y in A may be one or more, and if they are more, the respective substituents Y may be the same or different. In addition, the positions for the substitution of the substituents Y can be any position. The number of substituents Y in A is preferably 1. The number of halogen, alkyl or haloalkyl as the substituent for C3-4 cycloalkyl in Y may be 1 or more, and if more, the respective substituents may be the same or different. In addition, the positions for substitution for the respective substituents can be any position. The C3-4 cycloalkyl in Y is preferably unsubstituted, or when it has the above substituents, the number of said substituents is preferably from 1 to 5. As the halogen, or halogen as the substituent in R, R2, R3 or And, an atom of fluorine, chlorine, bromine or iodine. The number of halogens as a substituent may be one or more, and if they are more, the respective halogens may be the same or different. In addition, the positions for substitution of said halogens can be any position. The alkyl or the alkyl portion in R1, R2, R3, A or Y can be linear or branched. As its specific example, C 1-6 alkyl, such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl or hexyl may be mentioned. The alkenyl or the alkenyl portion in R1 may be linear or branched. As its specific example, C? -6 alkenyl such as vinyl, 1-propenyl, allyl, isopropenyl, 1-butenyl, 1,3-butadienyl or 1-hexenyl can be mentioned. The alkynyl or the alkynyl portion in R1 may be linear or branched. As its specific example, C2-β alkyl such as ethynyl, 2-butynyl, 2-pentynyl or 3-hexynyl can be mentioned. As a specific example of C3-4 cycloalkyl or cycloalkyl portion Y, cyclopropyl or cyclobutyl may be mentioned, and cyclopropyl is particularly preferred. The salt of anthranilamide compound of the formula (I) above includes all classes as long as they are agriculturally acceptable. For example, an alkali metal salt such as a sodium salt or a potassium salt; an alkaline earth metal salt such as magnesium salt or calcium salt; an ammonium salt such as dimethylammonium salt or a triethylammonium salt; an organic acid salt such as hydrochloride, perchlorate, or sulfate or a hydrate; or an organic acid salt such as acetate or a methanesulfonate, may be mentioned. The anthranilamide compound of the formula (I) may have optical isomers or geometric isomers, and said isomers and mixtures thereof both include in the present invention. In addition, in the present invention, several different isomers of those already mentioned above can be included within the scope of common knowledge in this technical field. In addition, depending on the type of said isomer, the chemical structure may be different from the aforementioned formula (I), but it is obvious to one skilled in the art that said structure is in isomeric relationship and therefore falls within the scope of the present invention. The anthranilamide compound of the above formula (I) or its salt (hereinafter simply referred to as the compound of the present invention) can be produced by the following reactions (A) and (B) and according to the usual method for producing a salt R1, R2, R3, A, m, n and q are as defined above and Z is a chlorine atom, -OH or C -? - alkoxy. In the case where Z is a chlorine atom, reaction (A) can usually be carried out in the presence of a base. As the base, one or more types can be suitably selected for use of, for example, an alkali metal hydroxide, such as sodium hydroxide, or potassium hydroxide, and alkali metal carbonate such as sodium carbonate or potassium carbonate.; an alkali metal hydride such sodium hydride or potassium hydride; and a tertiary amine such as trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2,6-dimethylpyridine, 4-pyrrolidinopyridine, N-methylmorpholine, N, N-dimethylaniline, N, N-diethylaniline, N-ethyl-N-methylaniline, 1,8-diazabicyclo [5.4.0] -undecene or 1,4-diazabicyclo [2.2.2] octane. The base can be used in an amount about 1 to 5 times per mole, preferably 1 to 2.5 times per mole, the compound of the formula (II). In the case where Z is a chlorine atom, reaction (A) can be carried out in the presence of a solvent, as the case requires. The solvent can be any solvent while it is an inert solvent for the reaction. For example, one or more types may suitably be selected for use of, for example, an ether such as diethyl ether, butylethyl ether, tetrahydrofuran, dioxane or dimethoxyethane; a halogenated hydrocarbon such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrafluoride, dichloroethane, trichloroethane or dichloroethylene; an aromatic hydrocarbon such as benzene, toluene, or xylene; a bipolar aprotic solvent such as acetonitrile, propionitrile, N, N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide or N-methylpyrrolidone; an ester such as methyl acetate, ethyl acetate, or propyl acetate; and a ketone such as acetone, diethyl ketone, methyl ethyl ketone or methyl isobutyl ketone. In the case where Z is a chlorine atom, reaction (A) can be carried out usually from -20 to + 60 ° C, preferably from 0 to 30 ° C. The reaction time is usually from about 1 to 24 hours, preferably from 2 to 12 hours. In the case where Z is -OH, reaction (A) can usually be carried out in the presence of a dehydration condensation agent and a solvent. The dehydration condensation agent can, for example, be a carbodiimide, such as N, N'-dicyclohexylcarbodiimide, 1,3-diisopropylcarbodiimide or 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride; or others such as 1, 1'-carbonyl-bis-1 H-imidazole, phenyl dichlorophosphate, diethyl phosphorocyanidate, 1, 3,5-triaza-2,4,6-triphosphorin-2,2,4,4, 6,6-hexachloride, cyanuric chloride, isobutyl chloroformate, chlorosulfonyl isocyanate, or trifluoroacetic anhydride. The solvent can be any solvent as long as it is inert to the reaction. For example, one or more types may be suitably selected for use of, for example, an ether such as diethyl ether, ethyl butyl ether, tetrahydrofuran, dioxane or dimethoxyethane; a halogenated hydrocarbon, such chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, trichloroethane, or dichloroethylene; an aromatic hydrocarbon such as benzene, toluene, or xylene; a bipolar aprotic solvent such as acetonitrile, propionitrile, N, N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide or N-methylpyrrolidone; an ester such as methyl acetate, ethyl acetate or propyl acetate; a ketone such as acetone, diethyl ketone, methyl ethyl ketone, or methyl isobutyl ketone; and an aliphatic hydrocarbon such as pentane, hexane, heptane, octane, or cyclohexane. In the case where Z is -OH, the reaction (A) can be carried out usually from -20 to + 60 ° C, preferably from 0 to 30 ° C. The reaction time is usually from about 0.5 to 24 hours, preferably from 1 to 12 hours. In the case where Z is C- [alpha] alkoxy, the reaction (A) can be carried out usually in the presence of a base and a solvent. As the base, one or more types may be suitably selected for use of, for example, an alkali metal hydride such as sodium hydride or potassium hydride.; an alkali metal alkoxide such sodium methoxide, sodium ethoxide, or tertiary potassium butoxide; and a tertiary amine such as trimethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2,6-dimethylpyridine, 4-pyrrolidinopyridine, N-methyl morpholine, N, N-dimethylaniline, N, N-diethylaniline, N-ethyl- N-methylaniline, 1,8-diazabicyclo [5.4.0] -7-undecene or 1,4-diazabicyclo [2.2.2] octane. The base can be used in an amount of about 1 to 5 times per mole, preferably 1 to 2.5 times per mole, for the compound of the formula (II). The solvent can be any solvent as long as it is inert to the reaction. For example, one or more types may be suitably selected for use of, for example, an ether such as diethyl ether, butylethyl ether, tetrahydrofuran, dioxane, or dimethoxyethane; an aromatic hydrocarbon such as benzene, toluene, or xylene; a bipolar aprotic solvent such as acetonitrile, propionitrile, N, N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide or N-methylpyrrolidone and an alcohol such as methanol, ethanol, propanol, n-butanol or tert-butanol . In the case where Z is C 1-4 alkoxy, the reaction (A) can be carried out usually from 0 to 120 ° C, preferably from 20 to 80 ° C. The reaction time is usually from about 0.5 to 24 hours, preferably from about 1 to 12 hours. The compound of the formula (II) or (III) above can be a known compound or can be produced according to the known reference materials. For example, the compound of the formula (II) can be produced through or according to the method described in Synthesis, 1980, p. 505. The compound of the formula (III) can be produced through or according to the method described in schemes 9 to 22 in WO03 / 24222.

R1, R2, R3, A, m, n and q are as defined above. Reaction (B) can be carried out usually in the presence of a solvent. The solvent can be any solvent as long as it is inert to the reaction. For example, one or more types may be suitably selected for use of, for example, an ether such as diethyl ether, ethyl butyl ether, tetrahydrofuran, dioxane or dimethoxyethane; a halogenated hydrocarbon such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, trichloroethane or dichloroethylene; an aromatic hydrocarbon such as benzene, toluene or xylene; a bipolar aprotic solvent such as acetonitrile, propionitrile, N, N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide or N-methylpyrrolidone. Reaction (B) can be carried out usually from 0 to 120 ° C, preferably from 20 to 80 ° C. The reaction time is usually about 0.5 to 24 hours, preferably about 1 to 12 hours. The compound of the formula (IV) above can be any known compound or can be produced according to the known reference material. For example, the compound of the formula (IV) can be produced through or according to the method described in Org. Prep. Proceed. Int., 1993, vol. 25, p. 585 or the method described in schemes 8 to 10 in WO03 / 2422. The compound of the formula (V) above includes a novel compound. Said compound can be produced by the Gabriel method, and can be produced, for example, according to the following reaction (C).

In the reaction (C) is defined as above, and T is halogen, -OS02G is a sulfonate residue) or -OH. When T is halogen or -OSO2G, M is sodium or potassium, and when T is -OH, M is a hydrogen atom. The above sulfonate residue may, for example, be a C? -6 alkyl, such as methyl or ethyl; or phenyl which may be substituted by the C? -6 alkyl. In the case where T is halogen or -OSO2, and M is sodium or potassium, the first step of the reaction (C) can usually be carried out in the presence of a solvent. The solvent can be any solvent while it is inert to the reaction, for example, one or more types can be suitably selected for use of, for example, an ether such as diethyl ether, ethyl butyl ether, tetrahydrofuran, dioxane, or dimethoxyethane; an aromatic hydrocarbon such as benzene, toluene or xylene; a bipolar aprotic solvent such as acetonitrile, propionitrile, N, N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide or N-methylpyrrolidone; and an alcohol such as methanol, ethanol, propanol, n-butanol or tert-butanol. In the case where T is halogen or -OS02G, and M is sodium or potassium, the first step of the reaction (C) can be carried out usually from 0 to 150 ° C, preferably from 30 to 110 ° C. The reaction time is usually 0.5 to 24 hours, preferably 1 to 12 hours. In the case where T is -OH and M is a hydrogen atom, the first step of the reaction (C) can usually be carried out through the Mitsunobu method. For example, it can be carried out using a dialkyl azo dicarboxylate, and triphenylphosphine in the presence of a solvent. Each of said dialkyl azo dicarboxylates and triphenylphosphine can usually be used in an approximately equimolar amount to the compound of the formula (VI). The dialkyl azodicarboxylate above can, for example, be diethyl azo dicarboxylate, or diisopropyl azo dicarboxylate. The solvent can be any solvent as long as it is inert to the reaction. For example, one or more types may be suitably selected for use of, for example, an ether such as diethyl ether, ethyl butyl ether, tetrahydrofuran, dioxane or dimethoxyethane; a halogenated hydrocarbon such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, trichloroethane or dichloroethylene; and an aromatic hydrocarbon such as benzene, toluene or xylene. In the case where T is -OH and M is a hydrogen atom, the first step of the reaction (C) can be carried out usually from 0 to 80 ° C, preferably from 20 to 60 ° C. The reaction time is usually from about 0.5 to 24 hours, preferably from 1 to 16 hours. The second step of the reaction (C) can usually be carried out through the decomposition of the compound of the formula (VIII) by means of hydrazine in the presence of a solvent. Said hydrazine can be used in an approximately equimolar amount to the compound of the formula (VIII). The solvent can be any solvent as long as it is inert to the reaction. For example, one or more types may be suitably selected for use of, for example, an ether, such as diethyl ether, ethyl butyl ether, tetrahydrofuran, dioxane or dimethoxyethane; an aromatic hydrocarbon such as benzene, toluene or xylene; and an alcohol such as methanol, ethanol, propanol, n-butanol or tert-butanol. The second step of the reaction (C) can be carried out usually from 0 to 140 ° C, preferably from 30 to 100 ° C. The reaction time is usually from about 0.5 to 24 hours, preferably from about 2 to 12 hours. Preferred embodiments of the pesticides containing the compounds of the present invention are described below. Pesticides containing the compounds of the present invention are particularly useful, for example, as agents for controlling pests that become problematic in agricultural and horticultural fields, that is, agricultural and horticultural pesticides, or as agents for controlling pests that are parasitic in animals, that is, pesticides against parasites in animals. The agricultural and horticultural pesticides containing the compound of the present invention are useful as an insecticide, a miticide, a nematicide, and a soil pesticide, and are effective in controlling parasitic mites in plants such as the two-spotted spider mite ( Tetranychus urticae), the carmine spider mite (Tetranychus cinnabarinus), the kanzawa spider mite (Tetranychus kanzawai), the red citrus mite (Panonychus citri), the European red mite (Panonychus ulmi), the broad mite (Polyphagotarsonemus latus), the pink citrus oxide mite (Acupulops pelekassi) and the bulb mite (Rhizoglyphys echinopus); the pests of agricultural insects such as the moth with diamond back (Plutella xylostella), the cabbage moth worm (Mamestra brassicae), the common moth larva (Spodoptera litura), the small apple moth (Laspeyresia pomonella), caterpillar (Heliothis zea), tobacco caterpillar (Heliothis virescens), gypsy moth (Lymantria dispar), the corn leafroller (Cnaphalocrocis medinalis), Asoxophyes sp., The summer fruit tortrix (Adoxophyes orana fascista), fruit moth of peach (Carposina niponensis), oriental fruit moth (Grapholita molesta), black moth larvae (Agrotis ipsilon), moth larvae (Agrotis segetum), colorado leg beetle (Leptinotarsa decemlineatal), cucurbit leaf beetle (Aulacophora) femoralis), baga weevil (Anthonomus grandis), aphids, plant grasshoppers, leafhopper, plates, bugs, whiteflies, aphids, grasshoppers, antomiid flies, beetles, ants, drilling flies, e leaves, plant parasitic nematodes, such as root knot nematodes, cyst nematodes, root-knot nematodes, white-tipped rice nematodes (Aphelenchoides besseyi), strawberry shoot nematode (Nothotylenchus acris), forest nematode of pines (Bursaphelenchus lignicolus); gastropods such as slugs and snails; soil pests such as isopods such as bugs in the form of a pill (Armadilidium vulgare) and bugs in the form of a pill (Porcellio scaber); hygienic insect pests such as the tropical rat mite (Ornithosyssus bacoti), house fly (Musca domestica), home mosquito (Culex pipiens) and cockroaches; insect pests of stored grain such as the moth angoumois (Sitotroga cerealella), adzuki bean weevil (Callosobruchus chinensis), red flour beetle (Tribolium castaneum) and mealworm; insect pests of clothing, home and household such as the mite of clothing manufacturer of caps (Tinea Pellionella), black carpet beetle (Anthrenus scrophularidae) and subterranean termites; house mites such as mold mite (Tyrophagus putrescentiae), Dermatophagoides pharynx and Chelacaropsis moorei. Among these, agricultural and horticultural pesticides contain the compounds of the present invention which are particularly effective in controlling plant parasitic mites, agricultural insect pests, plant parasitic nematodes or the like. In addition, they are effective against insect pests that have acquired resistance to organ phosphorus, carbate and / or synthetic pyrethroid insecticides. In addition, the compounds of the present invention have excellent systemic properties, and through the application of the compounds of the present invention to soil treatment, not only the noxious insects, noxious mites, noxious nematodes, noxious gastropods, and noxious isopods in the soil but also the foliage pests can be controlled. Other preferred embodiments of the pesticides containing compounds of the present invention may be agricultural and horticultural pesticides which collectively control the aforementioned plant parasitic mites, agricultural insect pests, plant parasitic nematodes, gastropods and soil pests. The agricultural and horticultural pesticides containing the compound of the present invention are usually formulated through the mixture of the compound with various agricultural adjuvants and used in the form of a formulation such as a powder, granules, granules dispersible in water, powder. wettable, water-based suspension concentrate, oil-based suspension concentrate, water-soluble granules, an emulsifiable concentrate, a soluble concentrate, a paste, an aerosol, or an ultra-low volume formulation. However, while they are suitable for the purpose of the invention, they can be formulated in any type of formulation that is commonly used in this field. Such agricultural adjuvants include solid carriers such as diatomaceous earth, quicklime, salt carbonate, calcium, talcum, white carbon, kaolin, bentonite, a mixture of kaolinite and sericite, clay, sodium carbonate, sodium bicarbonate, mirabilite, zeolite and starch; solvents such as water, toluene, xylene, naphtha solvent, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N, N-dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, and alcohol; anionic surfactants and propagators such as the fatty acid salt, a benzoate, an alkyl sulfosuccinate, a dialkylsulfosuccinate, a polycarboxylate, an alkylsulfuric acid ester salt, an alkyl sulfate, an alkylaryl sulfate, an alkyl diglycol ether sulfate, an ester salt of sulfuric acid ester, an alkyl sulfonate, an alkylaryl sulfonate, an aryl sulfonate, a lignin sulfonate, an alkyldiphenyl ether disulfonate, a polystyrene sulfonate, an ester salt of alkyl phosphoric acid, an alkylaryl phosphate, a styrylaryl phosphate, a polyoxyethylene alkyl ether salt of sulfuric acid ester, a polyoxyethylene alkyl aryl ether sulfate, a polyoxyethylene alkyl aryl ether ether salt of sulfuric acid, a polyoxyethylene alkyl ether phosphate, a salt of polyoxyethylene alkyl aryl ether of phosphoric acid, and a salt of a sulfonate condensate of naphthalene with formalin; nonionic surfactants and spreaders such as sorbitan fatty acid ester, a glycerin fatty acid ether, polyglycerol of fatty acid, an ether of polyglycol alcohol of fatty acid, acetyl glycol, acetyl alcohol, an oxyalkylene block polymer, a polyoxyethylene alkyl ether, a polyoxyethylene alkyl aryl ether, a polyoxyethylene styrylarylether, an ether polyoxyethylene glycol alkyl, a polyethylene glycol, a polyoxyethylene fatty acid ether, a polyoxyethylene sorbitan fatty acid ester, a polyoxyethylene glycerin fatty acid ester, a hydrogenated polyoxyethylene castor oil, and a polyoxypropylene ester; and vegetable and mineral oils such as olive oil, capoc oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, bran rice oil, peanut oil, oil of corn seed, soybean oil, rapeseed oil, linseed oil, tung oil, and liquid paraffins. Each of the components as such adjuvants may be one or more suitably selected for use, while the purpose of the invention can therefore be achieved. In addition, various additives that are commonly used, such as fillers, binders, an anti-settling agent, an antifreeze agent, a dispersion stabilizer, a cytotoxicity reducing agent, and an anti-mold agent, can also be used. The weight ratio of the compound of the present invention to the various agricultural adjuvants is usually from 0.001: 99.999 to 95: 5, preferably from 0.005: 99.995 to 90:10. In the current application of said formulation, it can be used as is or can be diluted to a predetermined concentration with a diluent such as water, and several spreaders, for example, surfactants, vegetable oils or mineral oils can be added thereto. , as the case may require. The application of the agricultural and horticultural pesticide containing the compound of the present invention generally can not be defined, since it varies depending on weather conditions, the type of the formulation, the application station, the application site, or the types or degrees of the outbreak of pest insects. However, it is usually applied at a concentration of the active ingredient being from 0.05 to 800,000 ppm, preferably from 0.05 to 500,000 ppm, and the dose per unit area is such that the compound of the present invention is from 0.05 to 50,000 g, preferably from 1 to 30,000 g, per hectare. In addition, agricultural and horticultural pesticides as another preferred embodiment of the pesticides containing the compounds of the present invention may be applied in accordance with the pesticide application described above. The present invention includes said method for controlling pests, particularly for controlling plant parasitic mites, agricultural insect pests or plant parasitic nematodes through said applications. The various formulations of agricultural and horticultural pesticides contain the compound of the present invention or their diluted compositions can be applied from conventional methods for application which are commonly used such as spraying (eg, spray, jet, fog, atomization, distribution of powders or grains or dispersion in water), application in the soil (for example, mixing or soaking, surface application eg coating, spraying or coating) or impregnation to obtain the poisoned food. In addition, it is possible to feed domestic animals with the food containing the above active ingredient and to control the outbreak or growth of pests, particularly insect pests, with their droppings. In addition, the active ingredient can also be applied through the so-called ultra low volume application method. In this method, the composition can be made up of 100% of the active ingredient. In addition, agricultural and horticultural pesticides containing the compounds of the present invention can be mixed with or used in combination with other chemicals, fertilizers, or agricultural cytotoxicity reducing agents, while sometimes the synergistic effects or activities can be obtained. Said other agricultural chemicals include, for example, a herbicide, an insecticide, a miticide, a nematicide, a soil pesticide, a fungicide, an anti-virus agent, an attractant, an antibiotic, a plant hormone, and a growth regulating agent. of plant. Especially, with a mixed pesticide having a compound of the present invention mixed or used in combination with one or more active compounds of other agricultural chemicals, the scale of application, the time of application, pesticide activities, etc., can be improved to preferred directions. The compound of the present invention and the active compounds of other agricultural chemicals can be formulated separately so that they can be mixed for use at the time of application, or can be formulated together. The present invention includes said mixed pesticidal composition. The mixing ratio of the compound of the present invention with the active compounds of other agricultural chemicals can not be generally defined, since it varies depending on the weather conditions, the types of formulations, the time of application, the site of application, the types or degrees of outbreaks of insect pests, etc., but is usually within the range of about 1: 300 to 300: 1, preferably 1: 100 to 100: 1, by weight. In addition, the dose for the application is such that the total amount of the active compounds is 0.1 to 50,000 g, preferably 1 to 30,000 g, per hectare. The present invention includes a method for controlling pests through the application of said mixed pesticidal composition. The active compounds of insect pest control agents such as insecticides, miticides, nematicides, or soil pesticides, in the other agricultural chemicals mentioned above, include, for example (by common names some of them are still in the application stage) organic phosphate compounds such as Profenofos, Dichlorvos, Fenamiphos, Fenitrotion, EPN, Diazinon, Chlorpyrifos-methyl, Acefate, Protiofos, Fostiazate, Fosfocarb, Cadusafos, Disulfoton, Chlorpyrifos, Demeton-S-methyl, Dumetoate, Methamidophos and Paration; carbamate compounds such as Carbaril, Propoxur, Aldicarb, Carbofuran, Thiodicarb, Methomyl, Oxamyl, Etiofencarb, Pirimicarb, Fenobucarb, Carbosulfan, and Benfuracarb; nereistoxin derivatives such as Cartap, and Tiociclam, and Bensultap; organic chlorine compounds such as Dicofol, Tetradifon and Endosulfan; organometallic compounds such as fenbutatin oxide; pyrethroid compounds such as Fenvalerate, Permethrin, Cypermethrin, Deltamethrin, Cihalotrin, Tefluthrin, Etofenprox, Fenpropatrin and Bifentrin; benzoylurea compounds such as Diflubenzuron, Clorfluazuron, Teflubenzuron, Flufenoxuron, Lufenuron, Novaluron, Bisfluron and Noviflumuron; juvenile hormone-type compounds such as Metoprene, Pyriproxyfen, and Phenoxycarb; pyridazinone compounds such as pyridaben; pyrazole compounds such as Fenpyroximate, Fipronil, Tebufenpyrad, Etiprole, Tolfenpirad, Acetoprole, Pirafluprole and Pyriprole; neonicotinoids such as Imidacloprid, Nitenpyram, Acetamiprid, Thiacloprid, Thiamethoxam, Clotianidin, and Dinotefuran; hideazine compounds such as Tebufenozide, Methoxyfenozide, Chromafenozide and Halofenozide; dinitro compounds, organic sulfur compounds, urea compounds, thiamine compounds, hydrazone compounds; and other compounds, such as Flonicamid, Buprofezin, Hexitiazox, Amitraz, Clordimeform, Silafluofen, Triazamate, Pimetrozine, Pirimidifen, Chlorfenapyr, Indoxacarb, Acequinocyl, Etoxazole, Ciromazine, 1,3-dichloropropene, Diafentiuron, Benclotiaz, Flufenerim, Piridalil, Spirodiclofen, Bifenazate, Spiromesifen, Propargite, Clofentezine, Fluacripirim, Flubendiamide, Ciflumetofen, Metaflumizone and Amidoflumet. In addition, microbial agricultural chemicals such as T agents, insect viruses, entomopathogenic fungi, and nematophagous fungi, antibiotics such as Avermectin, Emamectin-Benzoate, Milbemectin, Spinosad, Ivermectin and Lepimectin or natural products such as Azadiractin, and Rotenone, they can be used mixed or in combination. The active compounds of the fungicides among the other agricultural chemicals mentioned above, include, for example, (by names, some of which are still in the application stage) pyrimidinamine compounds such as Mepanipyrim, Pyrimethanil, and Ciprodinil; azole compounds such as Triadimefon, Bitertanol, Triflumizol, Etaconazole, Propiconazole, Penconazole, Flusilazole, Miclobutanil, Ciproconazole, Terbuconazole, Hexaconazole, Furconazole-cis, Prochloraz, Metconazole, Epoxiconazole, Tetraconazole, Oxpoconazole, and Sipconazole; quinoxaline compounds such as Quinomethionate; dithiocarbamate compounds such as Maneb, Zineb, Mancozeb, Polycarbamate, Propineb; organic chlorine compounds such as Ftalide, Chlorothalonil, and Quintozeno; imidazole compounds such as Benomyl, Thioanate-Methyl, Carbendazin, and Ciazofamid; pyridinamine compounds such as Fluazinam; cyanoacetamide compounds such as Cimoxanil; phenylamine compounds such as Metalaxyl, Oxadixil, Ofurace, Benalaxil, Furalaxil, and Ciprofuram; sulfenic acid compounds such as Diclofluanid; copper compounds such as cupric hydroxide, and copper oxine; isoxazole compounds such as hydroxyisoxazole; organophosphorus compounds such as Fosetil-AI, Tolclofos-Methyl, S-benzyl O, 0-diisopropylphosphorothioate, O-ethyl S, S-diphenylphosphorodiatioate, and aluminumethylhydrogen phosphonate; N-halogenothioalkyl compounds such as Captan, Captafol, and Folpet; dicarboximide compounds such as Procymidone, Iprodione, and Vinclozolin; benzanilide compounds such as Flutolanil, Mepronil, and Zoxamide; piperazine compounds such as Triforin; pyridine compounds such as Pirifenox; carbinol compounds such as Fenarimol; and Flutriafol; piperidine compounds such as Fenpropidin; morpholine compounds such as Fenpropimorf; organotin compounds such as Fentin Hydroxide, and Fentin Acetate; Urea compounds such as Pencicuron; Cinnamic acid compounds such as Dimetomorf; phenylcarbamate compounds such as Dietofencarb; cyanopyrrole compounds such as Fludioxonil, and Fenpiclonil; Strobilurin compounds such as Azoxystrobin, Kresoxim-Methyl, Meinofen, Trifloxystrobin, Picoxystrobin, and Piraclostrobin; oxazolidinedione compounds such as Famoxadone; thiazole carboxamine compounds such as Etaboxam; silyl amide compounds such as Silthiofam; amino acid carbamate amide compounds such as Iprovalicarb; imidazolidine compounds such as Fenamidone; hydroxyanilide compounds such as Fenhexamid; benzenesulfonamide compounds such as Flusulfamide; anthraquinone compounds; crotonic acid compounds, antibiotics; and other compounds such as Isoprothiolane, Tricyclazole, Pyroquilon, Diclomezine,. Probenazol, Quinoxifen, Propamocarb Hydrochloride, Spiroxamine, Chloropicrin, Dazomet, and Metam-Sodium. In addition, agricultural chemicals that can be used mixed with or in combination with the compounds of the present invention can, for example, be active ingredient compounds in herbicides as described in Farm Chemicals Handbook (2002 edition), particularly e for the type of soil treatment. Pesticides against parasites in animals are effective in controlling, for example, external parasites that are parasitic on the body surface of host animals (such as the back, armpit, lower abdomen or inside the thighs) or internal parasites that are parasitic in the body of host animals (such as the stomach, intestinal tract, lung, heart, liver, blood vessels, subcutis or lymphatic tissues), but are particularly effective in controlling external parasites. External parasites can, for example, be acarine or parasitic fleas of animals. Their aspects are so many that it is difficult to list all of them, and therefore their typical examples will be given. The parasitic acarine of animals may, for example, be ticks such as Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis Campanulata, Haemaphysalis concinna, Haemaphysalis japonica, Haemaphysalis kitaokai, Haemaphysalis ias, Ixodes ovatus, Ixodes nipponensis, Ixodes persulcatus, Amblyomma testudinarium, Haemaphysalis megaspinosa, Dermacentor reticulatus, and Dermacentor taiwanesis; common red mite (Dermanyssus gallinae); mites of northern birds such as Orniyssus sylviarum, and Omiyssus bursa; thrombidoids such as Eutrombicula wichmanni, Leptotrombidium akamushi, Leptotrombidium pallidum, Leptotrombidium fuji, Leptotrombidium tosa, Neotrombicula autumnales, Eutrombicula alfreddugesi, and Helenicula miyagawai; cheyletidae such as Cheyletiella yasguri, Cheyletiella parasitivorax, and Cheyletiella blakei; sarcoptic mango mites such as Psoroptes cuniculi, Chorioptes bocis, Otodectes cynotis, Sarcoptes scabiei, and Notoedres cati; and Demodicidae such as Demodex canis. Pesticides against parasites in animals, which contain the compounds of the present invention are particularly effective for the control of ticks between them. Fleas may be, for example, externally parasitic wingless insects belonging to Siphonaptera, more specifically, fleas belonging to Publicidae, Ceratephyllus, etc. The fleas belonging to Publicidae can, for example, be Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Echidnophaga gallinaceous, Xenopsylla cheopis, Leptopsylla segnis, Nosopsyllus fasciatus, and Monopsyllus anisus. The pesticides against parasites in animals, which contain the compounds of the present invention are particularly effective for the control of fleas belonging to Pulicidae, particularly Ctenocephalides canis and Ctenocephalides felis, among them. Other external parasites can, for example, be sucking lice (Anplura) such as short-nosed lice (Haematopinus eurysternus), horse sucking lice (haematopinus asini), sheep louse, long-nosed lice (Linognathus vituli ), and head lice (Pediculus capitis); biting lice such as dog biting lice (Trichodectes canis); and blood-sucking dipterous insects such as the gadfly (Tabanus trigonus), small stinging mosquitoes (Culicoides schultzei), and horse fly (Simulium ornatum). In addition, internal parasites can be, for example, nematodes, such as lung worms, whipworms (Trichuris), tuberous worms, gastric parasites, ascaris, and filarioidea; tape worm such as Spirometra erinacei, Diphyllobothrium latum, Dipylidum caninum, Taenia multiceps, Echinococcus granulosus, Echinococcus multilocularis, trematode such as Schistosoma japonicum, Fasciola hepatica; and protoars such as coccidia, malaria parasites (Plasmodium malariae), sarcocyst, tosoplasma, and cryptosporidium. The host animals can be, for example, pets, pet animals, and poultry, such as dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (such as pigeons, parrots). , eulabes, Java sparrows, honey parrots, parrots and canaries), cows, horses, pigs, sheep, ducks, and chickens. Pesticides against parasites in animals, which contain the compounds of the present invention, are particularly effective for the control of parasitic pests in pet animals or domestic animals, especially for the control of external parasites, among them. Among pet animals or domestic animals, these are effective in dogs, cats, cows, and horses. When the compound of the present invention is used as a pesticide against parasites in animals, it can be used as it is or can be used together with suitable adjuvants, as formulated in various formulations such as powder, granules, tablets, a powder, capsules, a soluble concentrate, an emulsifiable concentrate, a water-based suspension concentrate, and an oil-based suspension concentrate. In addition to such formulations, they can be formulated in any type of formulation that is commonly used in this field, so long as it is suitable for the purpose of the present invention. The adjuvants to be used for the formulations can be, for example, anionic surfactants or nonionic surfactants, exemplified above as adjuvants for the formulation of agricultural and horticultural pesticides; a cationic surfactant such as cetyl trimethylammonium bromide; a solvent such as water, acetone, acetonitrile, monomethylacetamide, dimethylacetamide, dimethylformamide, 2-pyrrolidone, N-methyl-2-pyrrolidone, kerosene, triacetin, methanol, ethanol, isopropanol, benzyl alcohol, ethylene glycol, propylene glycol, polyethylene glycol, liquid polyoxyethylene glycol, butyl diglycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, n-butyl glycol ether, dipropylene glycol monomethyl ether, or dipropylene glycol n-butyl ether; an antioxidant such as butylhydroxyanisole, butylhydroxytoluene, ascorbic acid, sodium hydrogen sulfite, propyl gallate, or sodium thiosulfate; a coating film-forming agent such as polyvinylpyrrolidone, polyvinyl alcohol, or a copolymer of vinyl acetate and vinylpyrrolidone; vegetable oils and mineral oils as exemplified above as adjuvants for the formulation of agricultural and horticultural pesticides; a carrier such as lactose, sucrose, glucose, starch, wheat flour, corn powder, soy bean cake and meal, defatted barley rice, calcium carbonate or other commercially available feedstocks. One of the respective components of these adjuvants may suitably be selected for use, as long as they do not depart from the purpose of the present invention. In addition, other of the aforesaid adjuvants, some of them known in the art, can suitably be selected for use, and still additionally some of the various aforesaid adjuvants for use in the agricultural and horticultural field can be suitably selected for use. The proportion of the mixture of the compound of the present invention with the various adjuvants is usually from 0.1: 99.9 to 90:10. In the current use of said formulation, they can be used as they are or can be diluted to a predetermined concentration as a diluent such as water, and various spreaders (eg, surfactants, vegetable oils or mineral oils) can be added thereto. , as the case may require. The administration of the compound of the present invention in a host animal is carried out orally, or parenterally. As an oral administration method, a method for administering a tablet, a liquid agent, a capsule, a wafer, a sponge cake, a ground meat, or other food, containing the compound of the present invention can be mentioned. As a method of parenteral administration, there may be mentioned, for example, a method in the compound of the present invention is formulated in a suitable formulation and then incorporated into the body through, for example intravenous administration, intramuscular administration, intradermal administration , hypodermic administration, etc., a method where it is administered on the surface of the body through on-site treatment, pouring treatment, or spray treatment; or a method for embedding a fragment of resin or the like containing the compound of the present invention under the skin of the host animal. The dose of the compound of the present invention for the host animal varies depending on the method of administration, the purpose of administration, the symptom of the disease, etc., but is usually administered in a proportion of 0.01 mg to 100 g, preferably from 0.1 mg to 10 mg, per 1 kg of the body weight of the host animal. The present invention also includes a method for controlling a pest through the aforementioned method of administration or through the aforementioned dosage, particularly a method for controlling external parasites or internal parasites. Furthermore, in the present invention, there may be a case where by controlling parasitic pests in animals as described above, it is possible to prevent or cure various diseases of the host animal caused by this. Thus, the present invention also includes a preventive or therapeutic agent for an animal disease caused by a parasite, containing the compound of the present invention as an active ingredient, and a method of preventing or curing an animal disease caused by a parasite. When the compound of the present invention is used as a pesticide against parasites in animals, various vitamins, minerals, amino acids, nutrients, enzymes, antipyretics can be used., sedatives, antiphlogistics, fungicides, dyes, aromatic substances, preservatives, etc., mixed with or in combination with the adjuvants. In addition, depending on the case, it may be mixed or combined other animal drugs and agricultural chemicals, such as vermicides, anti-coccidial agents, insecticides, miticides, policides, nematocides, bactericides, or antibacterial agents for use, thus improving the effects that sometimes can be obtained. The present invention includes said mixed pesticidal composition having the various components previously mixed or combined for use, and further a method for controlling a pest by using it, particularly a method for controlling external parasites or internal parasites. Now, some of the preferred embodiments of the present invention will be exemplified. Among those exemplified, with respect to the following (1) to (8), two or more may optionally be optionally combined, and compounds based on said combinations are also preferred embodiments of the compounds of the present invention. In addition, pesticides, agricultural and horticultural pesticides, insecticides, miticides, nematicides, pesticides against parasites in animals, pesticides against external parasites in animals and preventive or therapeutic agents for animal diseases caused by parasites, containing the following compounds as active ingredients are also preferred embodiments in the present invention. In addition, methods for controlling pests, therefore, by applying effective amounts of the following compounds, are also preferred embodiments of the present invention. However, it should be understood that the present invention is not restricted by these means. (1) A compound of the formula (I) above wherein at least one of R1 is substituted at the 4-position, and said R1 is a fluorine atom or a chlorine atom. (2) A compound of the formula (I) above wherein at least one of R1 is substituted at the 4-position, and said R1 is a chlorine atom. (3) A compound of the formula (I) above wherein at least one of R1 is substituted at the 4-position, and said R1 is alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl , alkoxycarbonyl, haloalkoxycarbonyl, phenoxycarbonyl which may be substituted, nitro or formyl. (4) A compound of the formula (I) above wherein R2 is halogen, haloalkyl, or haloalkoxy. (5) A compound of the formula (I) above wherein R 3 is halogen. (6) A compound of the formula (I) above wherein R 3 is halogen and 3- or 5-monosubstituted or 3,5-disubstituted. (7) A compound of the formula (I) above wherein Y is cyclopropyl. (8) A compound of the formula (I) above wherein Y is cyclopropyl, and said cyclopropyl is substituted by 1 to 5 substituents selected from the group consisting of halogen, alkyl, and haloalkyl. (9) A compound of the formula (I) above wherein R is halogen, alkyl, haloalkyl, alkylcarbonyl or formyl; R2 is halogen, haloalkyl or haloalkoxy; R3 is halogen or haloalkyl; A is alkyl substituted by Y; Y is cyclopropyl which may be substituted by at least one substituent selected from the group consisting of halogen and alkyl; m is 1 or 2; n is 0; and q is 1. (10) A compound as defined in (9) above, wherein R1 is 2-monosubstituted, or 2-4-disubstituted, and R3 is 3-monosubstituted. (11) A compound of the formula (I) above wherein R 1 is halogen, alkyl, or haloalkyl, R 2 is halogen, haloalkyl, or haloalkoxy, R 3 is halogen, A is alkyl substituted by Y, Y is cyclopropyl, m is 2 , n is 2, and q is 1. (12) A compound as defined in (11) above wherein R1 is 2,4-disubstituted and R3 is 3-monosubstituted. (13) A compound as defined in (12) above wherein R 1 at position 4 is a chlorine atom. (14) A compound of the formula (I) which is represented by the formula (1-1): wherein R1a is halogen or alkyl; each of R1b and R1d is a hydrogen atom; R1c is alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, phenoxycarbonyl which may be substituted, nitro formyl; R2 is halogen, haloalkyl or haloalkoxy; R3a is halogen or haloalkyl, each of R3b, R3c and R3d is a hydrogen atom; A is alkyl substituted by Y; Y is cyclopropyl which may be substituted by from 1 to 5 substituents selected from the group consisting of halogen, alkyl, and haloalkyl; and n is 0. (15) A compound as defined in (14) above wherein R 1c is haloalkyl, alkylcarbonyl or formyl. (16) A compound as defined in (14) above wherein R c is haloalkyl. (17) A compound as defined in (14) above wherein Y is cyclopropyl. (18) A compound of the formula (I) which is represented by the formula (la): wherein R1 is halogen or alkyl; each of R2 and R3 is halogen or -CF3; A is alkyl substituted by Y; Y is C3-4 cycloalkyl which may be substituted by halogen or alkyl; m is 1 or 2; and n is 0 or 1. (19) A compound of the formula (I) which is represented by the above formula (Ia) wherein R 1 is halogen or alkyl; each of R2 and R3 which are independent of each other is halogen or -CF3; A is -X-Y; X is alkylene; Y is C3-4 cycloalkyl which may be substituted by halogen or alkyl; m is 1 or 2; and n is 0 or 1.

EXAMPLES Now, the present invention will be described with reference to the examples, but it should be understood that the present invention by no means is limited thereto. First, examples of preparation of the compound of the present invention will be described.

PREPARATION EXAMPLE 1 Preparation of N-r6-fr (cyclopropylmethyl) amino-1-carbon-2-methylphenyl-1- (3-chloro-2-pyridyl) -3- (trifluoromethyl) -1H-pyrazole-5-carboxamide (after mentioned as compound No. 1) 1.49 g of triethylamine was gradually added dropwise to a mixed solution comprising 0.8 g of cyclopropylmethylamine hydrochloride and 40 ml of tetrahydrofuran under cooling with ice, followed by stirring at room temperature for 30 minutes. Then, a solution comprising 1 g of 2- [1- (3-chloro-2-pyridyl) -3- (trifluoromethyl) -1 H -pyrazol-5-yl] -8- was gradually added dropwise. methyl-4H-3,1-benzoxazin-4-one and 10 ml of tetrahydrofuran. After completion of the dropwise addition, the mixed solution was reacted for 4 hours under reflux. After completion of the reaction, the solvent was distilled off under reduced pressure, and to the residue, ethyl acetate and water were added for extraction. The organic layer was washed and dried over anhydrous magnesium sulfate. The solvent was distilled under reduced pressure, and the residue was purified through silica gel column chromatography (eluent: n-hexane / ethyl acetate = 1/1) to obtain 0.54 g of the desired product having a melting point from 199.4 ° C.

PREPARATION EXAMPLE 2 Preparation of N-r4-chloro-2-methyl-6"rfa-methyl- (cyclopropylmethyl) amino] carbonill-phenin-3- (trifluoromethyl) -1- (3-chloro-2-pyridyl) -1H -pyrazol-5-carboxamide (later mentioned as compound No. 3). 1.37 g of triethylamine was gradually added dropwise to a mixed solution comprising 0.82 g of cyclopropylmethylamine hydrochloride and 40 ml of tetrahydrofuran under cooling with ice, followed by stirring at room temperature for 30 minutes. Then, a mixed solution comprising 1 g of 2- [1- (3-chloro-2-pyridyl) -3- (trifluoromethyl) -1 H -pyrazol-5-yl] -6 was gradually added dropwise. -chloro-8-methyl-4H-3, 1-benzoxazin-4-one and 10 ml of tetrahydrofuran. After completion of the dropwise addition, the mixed solution was reacted for 4 hours under reflux. After the reaction was complete, the solvent was distilled off under reduced pressure, and to the residue, ethyl acetate and water were added for extraction, the organic layer was washed with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate The solvent was distilled under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 1/1) to obtain 0.54 g of the desired product having a melting point of 210.0 ° C.

EXAMPLE OF PREPARATION 3 Preparation of N-r4-chloro-2-methyl-6-f [α-methyl- (cyclopropylmethyl) amino-1-carbonyl-3-bromo-1- (3-chloro-2-pyridyl) -1H - pyrazole-5-carboxamide (later mentioned as compound No. 9) 1.07 g of triethylamine was gradually added dropwise to a mixed solution comprising 0.65 g of cyclopropylmethylamine hydrochloride and 40 ml of tetrahydrofuran under cooling with ice, followed by stirring at room temperature for 30 minutes. Then, a mixed solution comprising 0.8 g of 2- [3-bromo-1- (3-chloro-2-pyridyl) -1 H -pyrazol-5-yl] -6-chloro was gradually added dropwise. -8-methyl-4H-3,1-benzoxazin-4-one and 10 ml of tetrahydrofuran. After completion of the dropwise addition, the mixed solution was reacted for 4 hours under reflux. After completion of the reaction, the solvent was distilled off under reduced pressure, and to the residue, ethyl acetate and water were added for extraction. The organic layer was washed with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified through silica gel column chromatography (eluent: n-hexane / ethyl acetate = 1/1) to obtain 0.33 g of the desired product having a melting point from 183.6 ° C.

PREPARATION EXAMPLE 4 Preparation of N-r2-bromo-4-chloro-6-rfa-methyl- (cyclopropylmethyl) amino-1-carbonin-pheno-3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazole-5 -carboxamide (later mentioned as compound No. 15) 1 g of triethylamine was gradually added dropwise to a mixed solution comprising 0.6 g of cyclopropylmethylamine hydrochloride and 40 ml of tetrahydrofuran under cooling with ice, followed by stirring at room temperature for 1 hour. Then, a mixed solution comprising 0.85 g of 2- [3-bromo-1- (chloro-2-pyridyl) -1H-pyrazol-5-yl] -6-chloro-8-methyl- was added gradually dropwise. 4H-3,1-benzoxazin-4-one and 10 ml of tetrahydrofuran. After completion of the dropwise addition, the mixed solution was reacted for 4 hours under reflux. After completion of the reaction, the solvent was distilled off, and to the residue, ethyl acetate and water were added for extraction. The organic layer was washed with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled under reduced pressure, and the residue was purified through silica gel column chromatography (eluent: n-hexane / ethyl acetate = 1/2) to obtain 0.7 g of the desired product having a melting point of 260.6 ° C. Now, typical examples of the compound of the present invention represented by formula (I) above will be given in Table 1. These compounds can be prepared through the above-described preparation examples or through the various above-mentioned processes for the production of the compound of the invention. In Table 1, No. represents the compound number.In addition, in Table 1, Me represents a methyl group, Et represents an ethyl group, Pr a isopropyl group, CPr a cyclopropyl group, CBu a cyclobutyl group, and Ph a phenyl group. In addition, in Table 1, A1 represents -CH2- [CPr], A2 -CH (Me) - [CPr], A3 -CH- [2-Me-CPr], A4 -CH2- [2,2-CI2- 1- Me-CPr], A5 -CH2- [1-Me-CPr], and A6 -CH (Me) - [CBu]. Also in the box 1, 2-Me-CPr represents a cyclopropyl group having a methyl group substituted at the 2-position, and CO2Ph (4-Cl) represents a phenoxycarbonyl group having a substituted chlorine atom at the 4-position of the phenyl group. The same applies to other similar descriptions. Also, in Table 1, n is 0 unless otherwise specified.

(H) TABLE 1 Now the test samples will be described.

EXAMPLE OF TEST 1 Test on the control of the effects against moth larvae (Spodoptera lituria) A segment of cabbage leaf was immersed for approximately 10 seconds in an insecticide solution prepared to bring the concentration of the compound of the present invention to 50 ppm or 3.1 ppm and dried with air. A filter paper was placed in a petri dish having a diameter of 9 cm, and the dry leaf segment of cabbage was placed there. Ten second larvae of common moth larvae of insect were released there and after putting a cover, they were left in a chamber at constant temperature at 25 ° C with illumination. Dead larvae were counted 5 days after release, and mortality was calculated through the following equation. Here, the dying insects counted as dead insects.

Mortality at 50 ppm was obtained with respect to the aforementioned compounds Nos. 8, 20 to 22, 25, 41, 91 to 93 and 96, while all the compounds showed high control effects with a mortality of at least 90% and mortality at 3.1 ppm was obtained with respect to the aforementioned compounds Nos. 1 to 3, 5, 9 to 19, 23, 24, 38 to 40, 42, 80, 81 and 90, while all the compounds showed highly control with a mortality of at least 90%. Mortality (%) = (number of dead insects / number of insects released) x 100.

EXAMPLE OF TEST 2 Tests of the effects of control on the silver leaf white fly (Hemisia argentifoli) Adult silver leaf white flies were released into cucumbers with only one true leaf left and the other leaves were cut and planted on a plateau, and they were allowed to lay eggs for about 8 hours. Then, they were left for 7 to 10 days in a chamber at constant temperature at 25 ° C with illumination. The number of births was counted and then the infested leaf was immersed for approximately 10 seconds in an insecticide solution prepared to bring a concentration of the compound of the present invention to 200 ppm or 50 ppm and dried with air. After treatment, it was left in a chamber at constant temperature at 25 ° C with illumination for approximately 10 to 14 days, after which the number of old insect larvae and the number of pupae was counted, and the protective value was obtained through the following equation. The protective value at 200 ppm was obtained with respect to the aforementioned compounds Nos. 11 and 21, while showing high control effects with a protective value of at least 80% and the protective value at 50 ppm was obtained with respect to the compounds previously mentioned Nos. 3, 9, 12, 14 to 20, 22, 38 and 39, while all the compounds showed high control effects with a protective value of at least 80%. Protective value (%) = (1 - ((taxCb) / (TbxCa))) x100 Ta: Number of old insect larvae plus the number of pupae after treatment with the treated section. Tb: Number of births before treatment in the treated section. Ca: Number of larvae of old insects plus the number of pupae after treatment in an untreated section. Cb: Number of births before treatment in an untreated section.

EXAMPLE OF TEST 3 Test to control the effects against green peach aphid (Myzus persicae).

The eggplant petiole leaving only an authentic leaf and planted in a pot, was covered with an adhesive label and then released approximately 2-3 wingless viviparous females of green peach aphids on the authentic leaf. After 2 days of release, the adult insects were removed, and the number of larvae counted. Then, the leaf of the eggplant infested with the larvae was immersed in an insecticidal solution prepared to bring a concentration of the compound of the present invention to 800 ppm, for about 10 seconds, then dried with air and left in a chamber of Constant temperature at 25 ° C with lighting. The number of surviving insects was counted 5 days after treatment, and mortality was calculated through the following equation. Mortality was obtained with respect to the aforementioned compounds Nos. 2, 9, 11, 14 to 18, 20, 22, 23, 38, 39, 42 and 90, while all the compounds showed high control effects with a mortality of at least 90% Mortality (%) = (1 - (number of insects that survived / number of insects treated)) x100 EXAMPLE OF TEST 4 Test to control the effects against cotton aphid (Aphis gossypii).

The eggplant petiole leaving only an authentic leaf and planted in a pot, was covered with an adhesive label and then released approximately 3-4 wingless viviparous females of cotton aphids on the authentic leaf. After 2 days of release, the adult insects were removed, and the number of larvae counted. The leaf of the eggplant infested with the larvae was immersed in an insecticidal solution prepared to bring a concentration of the compound of the present invention to 800 ppm, for about 10 seconds, then dried with air and left in a constant temperature chamber. at 25 ° C with lighting. The number of surviving insects was counted 5 days after treatment, and mortality was obtained in the same manner as in Test Example 3 above. Mortality was obtained with respect to the aforementioned compounds Nos. 16, 18 and 22, while all the compounds showed high control effects with a mortality of at least 90%.

EXAMPLE OF TEST 5 Test on the effects of control against perforator of serpentine leaves (Liriomyza trifolii).

A segment of bean leaf having serpentine leaf perforator eggs was uniformly placed there, immersed for approximately 10 seconds in an insecticidal solution prepared to bring a concentration of the compound of the present invention of 25 ppm or 12.5 ppm, and then dried with air. A wet paper filter was placed in a plastic cup having a diameter of 9 cm and a height of 4 cm, and the segment of dry bean leaf was placed there. After placing a cover on it, it was left in a constant temperature chamber at 25 ° C with illumination. The number of larvae of old insects and the number of pupae was counted for 6 to 8 days after treatment, and the protective value was calculated through the following equation. The protective value was obtained at 25 ppm with respect to the aforementioned compounds Nos. 9, 14 and 23, while all the compounds showed high control effects with a protective value of at least 90%, and the protective value at 12.5 ppm. obtained with respect to the aforementioned compounds Nos. 2, 3, 11, 12, 15 to 18, 20 and 22, while all the compounds showed high control effects with a protective value of at least 90%. Protective value (%) = (1 - ((number of old insect larvae plus number of pupae in traced section) / (number of old insect larvae plus number of pupae in untreated section))) x100.

EXAMPLE OF TEST 6 Test on the effects of control against Thrips palmi.

All the leaves except the first authentic leaf of cucumbers planted in a pot were cut, the remaining leaf was immersed for about 10 seconds in an insecticide solution prepared to bring a concentration of the compound of the present invention to 50 ppm and dried with air. After the segment of cucumber leaf infested with the first insect larva was placed on the above treated leaf. The next day, the leaf segment pepeno was removed, and the number of larvae moved to the treated leaf was counted. A moist filter paper was placed in a plastic cup having a diameter of 9 cm and a height of 4 cm, and the cut treated sheet was placed there. Then, after putting a cover on this, it was left in a constant temperature chamber at 25 ° C with illumination. The number of surviving insects was counted for 12 to 15 days after treatment, and the protective value was obtained in the same manner as in Test Example 2. The protective value was obtained with respect to the aforementioned compounds Nos. 11, 12, 16, 22, 38 and 39, while all the compounds showed high control effects with a protective value of at least 90%.

EXAMPLE OF TEST 7 Test on the effects of control against 28 stained hoses (Epilachna vigintioctopunctata).

One segment of eggplant leaf was immersed for approximately 10 seconds in an insecticidal solution prepared to bring a concentration of the compound of the present invention to 25 ppm or 12.5 ppm and dried with air. A moist filter paper was placed in a plastic cup having a diameter of 9 cm and a height of 4 cm, and a segment of dry eggplant sheet was placed there. 5 first - second insect larvae of the 28 ladybugs stained there were released, and after putting a cover on this, it was left in a chamber at constant temperature at 25 ° C with illumination. Dead insects were counted for 4 to 6 days after release, and mortality was obtained in the same manner as in Test Example 1 above. Here, the dying insects were counted as dead insects. Mortality was obtained at 25 ppm with respect to the aforementioned compounds Nos. 9 and 11, while all the compounds showed high control effects with a mortality of at least 90%, and mortality was obtained at 12.5 ppm with respect to to the aforementioned compounds Nos. 3, 16, 22, 38 and 39, while all the compounds showed high control effects with a mortality of at least 90%.

EXAMPLE OF TEST 8 Test on the effects of control against the housefly (Musca domestica). g of the culture medium was placed in a plastic cup having a diameter of 6 cm and a height of 3 cm, and then, 10 ml of an insecticide solution prepared to bring the concentration of the compound of the present were added and mixed. invention at 200 ppm. 20 or 30 larvae of 4 days of age were released and after placing a cover on them, a chamber of constant temperature was left at 25 ° C with illumination for 15 to 16 days. Next, the number of adults was counted, and the percentage of emergency inhibition was obtained through the following equation. The percentage of emergency inhibition was obtained with respect to the aforementioned compounds Nos. 3, 9, 11, 12 and 14 to 20, while all the compounds showed high control effects with an emergency inhibition percentage of at least 90% . The percentage of emergency inhibition (%) = (1 - (number of adults / number of larvae released)) x100.

EXAMPLE OF TEST 9 Test on the control effects against Formosan subterranean termite (Coptotermes formosanus).

A filter paper was placed in a glass petri duck having a diameter of 9 cm, and 1 ml of an insecticide solution prepared to bring the concentration of the compound of the present invention to 500 ppm was applied. After, 10 workers and a soldier of the underground termites of Formosa were released, and after putting a cover, they were left in a chamber of constant temperature at 25 ° C with illumination. The number of dead workers counted 6 days after treatment, and mortality was obtained to the following equation. Mortality was obtained with respect to the above compounds Nos. 3, 9, 11, 12, 14 to 16 and 22, while all the compounds showed high control effects with a mortality of at least 90%. Mortality (%) = (number of workers killed between 10) x100.

EXAMPLE OF TEST 10 Proof of the systemic effects against the larva of common moth (Spodoptera litura). ml of an insecticide solution prepared to bring the concentration of the compound of the present invention to 800 ppm or 200 ppm in the base of a cabbage was applied in the fifth or sixth stage of. the leaf planted in a pot. A wet filter paper was placed in the petri dish having a diameter of 9 cm, and a segment of the short cabbage leaf 10 days after the treatment was placed there. Ten second-third larvae of common moth larva insect were released there, and after placing a cover, they were left in a constant temperature chamber at 25 ° C with illumination. Dead larvae were counted for 4 to 5 days after release, and mortality was obtained in the same manner as in test example 1 above. Here, the dying insects were counted as dead insects. Mortality at 800 ppm was obtained with respect to the aforementioned compound No. 8 while showing high control effects with a mortality of at least 90%, and mortality at 200 ppm was obtained with respect to the aforementioned compounds Nos. 3 , 9, 11, 16, 18 and 22, while all the compounds showed high control effects with a mortality of at least 90%.

EXAMPLE OF TEST 11 Test on the effects of control against Haemphysalis longicornis.

It was applied dropwise on the inner surface of a petri dish having a diameter of 9 cm, 1 ml of acetone solution of a sample compound (concentration: 10 μg / ml) through a micropipette. On the other hand, as a control section, 1 ml of acetone was applied dropwise in the same manner. The inner surface of the petri dish was dried, and then approximately 100 tick larvae were placed, and the petri dish was covered with a polyethylene sheet and sealed with an elastic band. Next, except for the observation time, the petri dish was allowed to stand at a constant temperature of 25 ° C under a relative humidity of 100% and under a constant dark condition. The observation was carried out each time after placing the flea larvae in the petri dish (after 5 minutes, 10 minutes, 15 minutes, 20 minutes, 30 minutes, 45 minutes, 1 hour, 2 hours, 4 hours, 6 hours and 24 hours). The number of annihilated fleas after contact with the insecticide compound was recorded. The previous operation was repeated 2 times. The degree of annihilation at each observation time was corrected through the following abbott correction formula. Next, a linear probit-time line was drawn and the average annihilation time (KT50 value) was obtained. With respect to the KT50 values of the respective sample compounds, they were 9 minutes and 8 minutes with the aforementioned compound No. 3, and 7.5 minutes and 6 minutes with the above-mentioned compound No., while they were 80 minutes and 40 minutes. minutes with the next comparative compound A and 120 minutes and 80 minutes with the next comparative compound B. Degree of corrected annihilation (%) = [(degree not of annihilation in the control section - degree not annihilation in the section treated) / degree not annihilation in the control section] x100. Comparative compound A is the following compound which is compound 484 in WO03 / 24222, compound 497 in WO03 / 14418 and compound 2 in WO03 / 15519.

Comparative Compound A Comparative compound B is the following compound which is compound 509 in WO03 / 24222, compound 530 in WO03 / 15518 and compound 27 in WO03 / 15519.

Comparative Compound B EXAMPLE OF TEST 12 Test on the effects of control against cat flea (Ctenocephalides felis). 0. 5 ml of an acetone solution of the compound of the present invention prepared to be 5.3 ppm was dropped into a glass tube having a flat bottom (inner diameter: 2.6 cm, lower area: 5.3 cm2, height 12 cm). The acetone was evaporated at room temperature to have a dry film containing the compound of the present invention formed on the inner surface. Ten adults of the cat flea (still not being blood sucking adults within five days after adult emergence) were placed there and exposed to the compound of the present invention. The test was carried out continuously 3 times. Dead cat fleas were counted 48 hours after exposure and mortality was obtained in the same manner as Test Example 1 above. Mortality was obtained with respect to the aforementioned compound No. 16, while showing high control effects with a mortality of at least 90%.

EXAMPLE OF FORMULATION 1 (1) Compound of the present invention 20 parts by weight (2) Clay 72 parts by weight (3) Sodium lignin sulfonate 8 parts by weight The above compounds were mixed uniformly to obtain a wettable powder.

EXAMPLE OF FORMULATION 2 (1) Compound of the present invention 5 parts by weight (2) Talc 95 parts by weight The above compounds were mixed uniformly to obtain a powder.

EXAMPLE OF FORMULATION 3 (1) Compound of the present invention 20 parts by weight (2) N, N'-dimethylacetamide 20 parts by weight (3) polyoxyethylene alkylphenyl ether 10 parts by weight (4) Xylene 50 parts by weight The above compounds were uniformly mixed and dissolved to obtain an emulsifiable concentrate.

EXAMPLE OF FORMULATION 4 (1) Clay 68 parts by weight (2) Sodium lignin sulfonate 2 parts by weight (3) polyoxyethylenealkylaryl ether 10 parts by weight (4) Fine silica powder 25 parts by weight A mixture of the above compounds was mixed with the compound of the present invention in a weight ratio of 4: 1 to obtain a wettable powder.

EXAMPLE OF FORMULATION 5 (1) Compound of the present invention 50 parts by weight (2) Oxylated polyalkylphenyl phosphate-triethanolamine 2 parts by weight (3) Silicone 0.2 parts by weight (4) Water 47.8 parts by weight The above compounds were uniformly mixed and pulverized to obtain a base liquid, and (5) Sodium polycarboxylate 5 parts by weight (6) Anhydrous sodium sulfate 42.8 parts by weight were added, and the mixture was mixed uniformly, granulated and dried to obtain water dispersible granules.

EXAMPLE OF FORMULATION 6 (1) Compound of the present invention 5 parts by weight (2) Polyoxyethylene-ethylphenyl ether 1 part by weight (3) Polyoxyethylenephosphoric acid ester 0.01 parts by weight (4) Granular calcium carbonate 93.9 parts by weight The above compounds (1) (3) preliminarily they were uniformly mixed and diluted with an appropriate amount of acetone and then the mixture was sprayed on the component (4), and the ketone was removed to obtain granules.

EXAMPLE OF FORMULATION 7 (1) Compound of the present invention 2.5 parts by weight (2) N-methyl-2-pyrrolidone 2.5 parts by weight (3) Soy bean oil 95.0 parts by weight The above components were uniformly mixed and dissolved to obtain a formulation with an ultra low volume.

EXAMPLE OF FORMULATION 8 (1) Compound of the present invention 40 parts by weight (2) Oxylated polyalkylphenylphosphate-triethanolamine 2 parts by weight (3) Silicon 0.2 parts by weight (4) Zanthan gum 0.1 parts by weight (5) Ethylene glycol 5 parts by weight (6) Water 52.7 parts by weight The above compounds were uniformly mixed and pulverized to obtain a suspension concentrate based on water.

EXAMPLE OF FORMULATION 9 (1) Compounds of the present invention 10 parts by weight (2) Diethylene glycol monoethyl ether 90 parts by weight The above compounds were mixed uniformly to obtain a soluble concentrate. The full descriptions of Japanese Patent Application No. 2004-041295 filed on February 18, 2004, Japanese Patent Application No. 2004-133722 filed on April 28, 2004, Japanese Patent Application No. 2004-261507 filed on September 8, 2004, and Japanese Patent Application No. 2004-295778 filed October 8, 2004 include specifications, claims, and summaries that are incorporated herein by reference in their entirety.

Claims

NOVELTY OF THE INVENTION CLAIMS

1. - An anthranilamide compound represented by the formula (I) or its salt: wherein R1 is halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, phenoxycarbonyl which may be substituted, nitro or formyl; each of R2 and R3 which are independent of each other, is halogen, alkyl, haloalkyl, alkoxy, haloaxyxy, or cyano; A is an alkyl substituted by Y; Y is C3- cycloalkyl which may be substituted by at least one substituent selected from the group consisting of halogen, alkyl, and haloalkyl; m is from 0 to 4; n is from 0 to 1; and q is from 0 to 4; provided that when R1 is a fluorine atom, a chlorine atom, a bromine atom or methyl substituted at the 2-position of the benzene ring and the other R1 is halogen substituted at the 4-position of the benzene ring, the halogen in the position 4 is a fluorine atom or a chlorine atom.

2. - The compound or its salt according to claim 1, further characterized in that R1 is C1-6 alkyl, haloalkyl of C6-6, alkenyl of C2-6, haloalkenyl of C2-6, alkynyl of C2-6, haloalkynyl of C 2-6, C 1-6 alkoxy, C 1-6 haloalkoxy, C 1-6 alkylcarbonyl, C 1-6 haloalkylcarbonyl, C 1-6 alkoxycarbonyl, C 1-6 haloalkoxycarbonyl, phenoxycarbonyl which may be substituted, nitro or formyl; each R2 and R3 which are independent of each other, is halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy or cyano; A is C? -6 alkyl substituted by Y; Y is C3- cycloalkyl which may be substituted by at least one substituent selected from the group consisting of C1-6 alkyl and C6-6 haloalkyl; m is from 0 to 4; n is 0 or 1; and q is from 0 to 4.

3. The compound or its salt according to claim 1, further characterized in that the substituent for the phenoxycarbonyl may be substituted, for R1, it is at least one selected from the group consisting of alkyl, haloalkyl , alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyano and nitro.

4. The compound or its salt according to claim 1, further characterized in that the cycloalkyl of C3- for Y is unsubstituted.

5. The compound or its salt according to claim 1, further characterized in that the C3-4 cycloalkyl for Y is substituted by 1 to 5 substituents selected from the group consisting of halogen, alkyl and haloalkyl.

6. The compound or its salt according to claim 1, further characterized in that Y is cyclopropyl.

7. The compound or its salt according to claim 1, further characterized in that at least one of R1 is substituted at the 4-position, and said R1 is alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, phenoxycarbonyl which may be substituted, nitro or formyl.

8. The compound or its salt according to claim 1, further characterized in that R1 is halogen, alkyl, haloalkyl, alkylcarbonyl or formyl; R2 is halogen, haloalkyl, or haloalkoxy; R3 is halogen or haloalkyl; A is alkyl substituted by Y; Y is cyclopropyl which may be substituted by at least one substituent selected from the group consisting of halogen and alkyl; m is 1 or 2; n is 0; and q is 1.

9. The compound or its salt according to claim 1, further characterized in that R1 is halogen, alkyl, or haloalkyl; R2 is halogen, haloalkyl, or haloalkoxy; R3 is halogen; A is alkyl substituted by Y; And it is cyclopropyl; m is 2, n is 0; and q is 1. 10.- N- [6 - [[(cyclopropylmethyl) amino] carbonyl] -2-methylphenyl] -1- (3-chloro-2-pyridyl) -3- (trifluoromethyl) -1 H- pyrazole-5-carboxamide 11.- N- [4-chloro-2-methyl-6 - [[α-methyl- (cyclopropylmethyl) amino] carbonyl] -phenyl] -3- (trifluoromethyl) -1- (3-chloro -2-pyridyl) -1 H- pyrazole-5-carboxamide. 12.- N- [4-Chloro-2-methyl-6 - [[α-methyl- (cyclopropylmethyl) amino] carbonyl] -phenyl] -3-bromo-1- (3-chloro-2-pyridyl) -1 H-pyrazole-5-carboxamide. 13.- N- [2-bromo-4-chloro-6 - [[α-methyl- (cyclopropylmethyl) amino] carbonyl] -phenyl] -3-bromo-1- (3-chloro-2-pyridyl) -1 H-pyrazole-5-carboxamide. 14. A process for producing an anthranilamide compound represented by the formula (I) or its salt: where R1 is halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, phenoxycarbonyl which may be substituted, nitro or formyl; each of R2 and R3 which are independent of each other, is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, or cyano; A is an alkyl substituted by Y; Y is C3- cycloalkyl which may be substituted by at least one substituent selected from the group consisting of halogen, alkyl, and haloalkyl; m is from 0 to 4; n is from 0 to 1; and q is from 0 to 4; provided that when R1 is a fluorine atom, a chlorine atom, a bromine atom or methyl substituted at the 2-position of the benzene ring and the other R1 is halogen substituted at the 4-position of the benzene ring, the halogen in the position 4 is a fluorine atom or a chlorine atom, comprising, which comprises (1) reacting a compound represented by the formula (II): wherein R1, A and m are as defined above, with a compound represented by the formula (III): wherein R2, R3, n and q are as defined above, and Z is a chlorine atom, -OH or C-? - alkoxy, or (2) reacting a compound represented by formula (IV): (IV) wherein R1, R2, R3, m, n and q are as defined above, with a compound represented by the formula (V): A-NH2, wherein A is as defined above. 15. A pesticide containing the anthranilamide compound or its salt as defined in any of claims 1 to 13, as an active ingredient. 16. An agricultural and horticultural pesticide containing the anthranilamide compound or its salt as defined in any of claims 1 to 13, as an active ingredient. 17. An insecticide, miticide or nematicide containing the anthranilamine compound or its salt as defined in any of claims 1 to 13, as an active ingredient. 18. A pesticide against a parasite in animals, which contains the anthranilamide compound or its salt as defined in any of claims 1 to 13, as an active ingredient. 19. A pesticide against an external parasite in an animal, which contains the anthranilamide compound or its salt as defined in any of claims 1 to 13, as an active ingredient. 20. A preventive or therapeutic agent for an animal disease caused by a parasite, which contains the anthranilamide compound or its salt as defined in any of claims 1 to 13, as an active ingredient. 21. A method for controlling a pest, which comprises applying an effective amount of an anthranilamide compound or its salt as defined in any of claims 1 to 13.