CN1918144A - Anthranilamide compound, its production method and pest control agent containing the compound - Google Patents

Abstract

The present invention provides a novel anthranilamide compound or a salt thereof useful as a pest control agent, a method for producing the same, and a pest control agent containing the same as an active ingredient. Namely, an anthranilamide compound represented by the formula (1) or a salt thereof is provided. In the formula, R¹Is halogen, alkyl, haloalkyl, etc.; r²And R³Each independently is halogen, alkyl, haloalkyl, etc.; a is alkyl substituted by Y; y is C which may be substituted by at least 1 substituent selected from the group consisting of halogen, alkyl and haloalkyl_3－4A cycloalkyl group; m is 0 to 4; n is 0 or 1; q is 0 to 4.

Description

Anthranilamide compound, its production method and pest control agent containing the compound

technical field

Patent Document 1, Patent Document 2, Patent Document 3, and Patent Document 4 each disclose anthranilamide compounds having specific chemical structures. However, none of these patent documents describes a compound having A corresponding to A in the formula (I) of the present invention described later, where A is an alkyl group substituted with a C3-4 cycloalkyl group as a substituent.

In addition, Patent Document 5 discloses an anthranilamide compound having a cyano group at the 4-position of the benzene ring. However, the definition of R ¹ in the formula (I) of the present invention described later does not include a cyano group, and both have different chemical structures.

Patent Document 1: International Publication No. WO03/24222

Patent Document 2: International Publication No. WO03/15518

Patent Document 3: International Publication No. WO03/15519

Patent Document 4: International Publication No. WO01/70671

Patent Document 5: International Publication No. WO04/67528

Contents of the invention

Over the years, although many pest control agents have been used, many of them have various problems such as insufficient effects, restrictions on the use of pests after acquiring resistance, and the like.

The present invention seeks to develop a new pest control agent with few such disadvantages, for example, a pest control agent that can control various pests that are problematic in the field of agriculture and horticulture, or pests that parasitize animals.

The inventors of the present invention conducted various studies on anthranilamide-based compounds in order to find a more excellent pest control agent. As a result, it has been found that a novel anthranilamide compound or a salt thereof has a very high control effect against harmful organisms at a low dosage, thereby completing the present invention.

That is, the present invention relates to anthranilamide compounds represented by formula (I) or salts thereof, methods for producing the same, and pest control agents containing them, etc.

[chemical 1]

(wherein, ^R is halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkane Oxycarbonyl, haloalkoxycarbonyl, phenoxycarbonyl that may be substituted, nitro or formyl; ^R2 and ^R3 are independently halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or cyano ; A is an alkyl group substituted by Y; Y is a C3-4 cycloalkyl group that may be substituted by at least one substituent selected from the group consisting of halogen, alkyl and haloalkyl; m is 0 to 4; n is 0 or 1; q is 0 to 4, provided that ^R1 is a fluorine atom, a chlorine atom, a bromine atom or a methyl group substituted at the 2-position of the benzene ring, and other ^R1 is a halogen substituted at the 4-position of the benzene ring, The halogen at the 4-position is a fluorine atom or a chlorine atom).

The pest control agent that uses the novel anthranilamide compound of the above formula (I) as an active ingredient has a very high control effect on harmful organisms at a low dosage.

Detailed ways

Examples of substituents for the phenoxycarbonyl group that may be substituted in ^R include halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, and alkylsulfin Acyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyano, nitro, etc. The number of such substituents may be 1 or 2 or more, and in the case of 2 or more, each substituent may be the same or different. In addition, the substitution position of each substituent may be any position.

The number of substituents Y in A may be 1 or 2 or more, and in the case of 2 or more, each substituent Y may be the same or different. In addition, the substitution position of the substituent Y may be any position. The number of substitutions of the substituent Y in A is preferably 1.

The number of substitutions of halogen, alkyl or haloalkyl as a substituent of C3-4 cycloalkyl in Y may be 1 or 2 or more, and in the case of 2 or more, each substituent may be the same or different. In addition, the substitution position of each substituent may be any position. The C3-4 cycloalkyl group in Y is preferably unsubstituted, or when it has the above substituents, the number of substitutions is preferably 1-5.

Examples of the halogen in R ¹ , R ² , R ³ or Y or the substituent include each atom of fluorine, chlorine, bromine or iodine. The number of halogens as substituents may be 1 or 2 or more, and in the case of 2 or more, each halogen may be the same or different. In addition, the substitution position of halogen may be any position.

The alkyl or alkyl moiety in R ¹ , R ² , R ³ , A or Y may be either linear or branched. Specific examples thereof include C1-6 alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, and hexyl.

The alkenyl or alkenyl moiety in R ¹ may be either straight or branched. Specific examples thereof include vinyl, 1-propenyl, allyl, isopropenyl, 1-butenyl, 1,3-butadienyl, and 1-hexenyl such as C2-6 Alkenyl etc.

The alkynyl group or alkynyl moiety in R ¹ may be either linear or branched. Specific examples thereof include C2-6 alkynyl groups such as ethynyl, 2-butynyl, 2-pentynyl, and 3-hexynyl.

Specific examples of the C3-4 cycloalkyl or cycloalkyl moiety in Y include cyclopropyl or cyclobutyl, among which cyclopropyl is preferred.

The salts of the anthranilamide compounds of the formula (I) include all agriculturally acceptable salts. Examples include alkali metal salts such as sodium salt and potassium salt; alkaline earth metal salts such as magnesium salt and calcium salt; ammonium salts such as dimethylammonium salt and triethylammonium salt; hydrochloride and perchlorate , inorganic acid salts such as sulfate and nitrate; organic acid salts such as acetate and methanesulfonate, etc.

In the anthranilamide compound of the above formula (I), there may be isomers such as optical isomers and geometric isomers, and the present invention includes both the individual isomers and the mixture of isomers. In addition, the present invention also includes various isomers other than those described above within the scope of common technical knowledge in the technical field. In addition, although a chemical structure different from the above-mentioned formula (I) may be formed depending on the type of isomer, those skilled in the art can fully understand that this is the relationship between isomers, so it is obvious that in within the scope of the present invention.

The above-mentioned anthranilamide compound of the formula (I) or its salt (hereinafter simply referred to as the compound of the present invention) can be produced according to the following reactions [A] to [B] and the usual salt production method.

[Chem 2]

R ¹ , R ² , R ³ , A, m, n and q are as above, and Z is a chlorine atom, -OH or a C _1-4 alkoxy group.

When Z is a chlorine atom, the reaction [A] can usually be performed in the presence of a base.

As the base, for example, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal hydrides such as sodium hydride and potassium hydride; trimethylamine , triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2,6-lutidine, 4-pyrrolidine pyridine, N-methylmorpholine, N, N -Dimethylaniline, N,N-diethylaniline, N-ethyl-N-methylaniline, 1,8-diazabicyclo[5.4.0]-7-undecene, 1,4- One or two or more of tertiary amines such as diazabicyclo[2.2.2]octane. The base can be used in an amount of 1 to 5 times moles, preferably 1 to 2.5 times moles, based on the compound of formula (II).

When Z is a chlorine atom, the reaction [A] can be performed in the presence of a solvent if necessary. Any solvent may be used as long as it is inert to the reaction. For example, ethers such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane, and dimethoxyethane can be appropriately selected; chlorobenzene, dichlorobenzene, methylene chloride, chloroform, carbon tetrachloride, dichloroethane, etc. Halogenated hydrocarbons such as alkane, trichloroethane, and dichloroethylene; aromatic hydrocarbons such as benzene, toluene, and xylene; acetonitrile, propionitrile, N,N-dimethylformamide, dimethyl sulfoxide, Polar aprotic solvents such as hexamethylphosphoramide, sulfolane, dimethylacetamide, and N-methylpyrrolidone; esters such as methyl acetate, ethyl acetate, and propyl acetate; acetone, diethyl ketone, One or more of ketones such as methyl ethyl ketone and methyl isobutyl ketone.

When Z is a chlorine atom, the reaction [A] is usually carried out at -20 to +60°C, preferably at 0 to 30°C. The reaction time is usually about 1 to 24 hours, preferably about 2 to 12 hours.

When Z is -OH, the reaction [A] can usually be performed in the presence of a dehydrating condensation agent and a solvent.

Examples of dehydrating condensation agents include N,N'-dicyclohexylcarbodiimide, 1,3-diisopropylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl ) Carbodiimides such as carbodiimide hydrochloride; In addition, 1,1'-carbonyl-bis-1H-imidazole, phenyl dichlorophosphate, diethyl cyanophosphonate, 1 , 3,5-Triaza-2,4,6-triphosphine-2,2,4,4,6,6-hexachloro, cyanuric chloride, isobutyl chloroformate, chlorosulfonic acid isocyanate, trifluoro Acetic anhydride, etc.

As the solvent, any solvent may be used as long as it is inert to the reaction. For example, ethers such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane, and dimethoxyethane can be appropriately selected; chlorobenzene, dichlorobenzene, methylene chloride, chloroform, carbon tetrachloride, dichloroethane, etc. Halogenated hydrocarbons such as alkane, trichloroethane, and dichloroethylene; aromatic hydrocarbons such as benzene, toluene, and xylene; acetonitrile, propionitrile, N,N-dimethylformamide, dimethyl sulfoxide, Polar aprotic solvents such as hexamethylphosphoramide, sulfolane, dimethylacetamide, and N-methylpyrrolidone; esters such as methyl acetate, ethyl acetate, and propyl acetate; acetone, diethyl ketone, Ketones such as methyl ethyl ketone and methyl isobutyl ketone; one or more of aliphatic hydrocarbons such as pentane, hexane, heptane, octane, and cyclohexane.

When Z is -OH, the reaction [A] can be performed usually at -20 to +60°C, preferably at 0 to 30°C. The reaction time is usually about 05 to 24 hours, preferably about 1 to 12 hours.

When Z is a C _1-4 alkoxy group, the reaction [A] can usually be carried out in the presence of a base and a solvent.

As the base, for example, alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and sodium tert-butoxide; trimethylamine, triethylamine, triisopropylamine, diisopropylamine, and Propylethylamine, pyridine, 4-dimethylaminopyridine, 2,6-lutidine, 4-pyrrolidine pyridine, N-methylmorpholine, N,N-dimethylaniline, N,N-di Ethylaniline, N-ethyl-N-methylaniline, 1,8-diazabicyclo[5.4.0]-7-undecene, 1,4-diazabicyclo[2.2.2]octane One or more of such tertiary amines and the like. The base can be used in an amount of 1 to 5 times moles, preferably 1 to 2.5 times moles, based on the compound of formula (II).

As the solvent, any solvent may be used as long as it is inert to the reaction. For example, ethers such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane, and dimethoxyethane can be appropriately selected; aromatic hydrocarbons such as benzene, toluene, and xylene; acetonitrile, propionitrile, N,N - Polar aprotic solvents such as dimethylformamide, dimethylsulfoxide, hexamethylphosphoramide, sulfolane, dimethylacetamide, N-methylpyrrolidone; methanol, ethanol, propanol, n-butanol, One or two or more types of alcohols such as tert-butanol.

When Z is a C _1-4 alkoxy group, the reaction [A] can be carried out usually at 0 to 120°C, preferably at 20 to 80°C. The reaction time is usually about 0.5 to 24 hours, preferably about 1 to 12 hours.

The above-mentioned compounds of formula (II) or formula (III) are known compounds respectively, or can be prepared according to known information. For example, the compound of formula (II) can be prepared according to the method described in Synthesis, 1980, p.505. The compound of formula (III) can be prepared according to the method described in Scheme 9-22 of WO03/24222.

[Chem 3]

R ¹ , R ² , R ³ , A, m, n and q are as described above.

Reaction [B] can usually be carried out in the presence of a solvent.

As the solvent, any solvent may be used as long as it is inert to the reaction. For example, ethers such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane, and dimethoxyethane; chlorobenzene, dichlorobenzene, methylene chloride, chloroform, carbon tetrachloride, dichloromethane, Halogenated hydrocarbons such as ethane, trichloroethane, and dichloroethylene; aromatic hydrocarbons such as benzene, toluene, and xylene; acetonitrile, propionitrile, N,N-dimethylformamide, and dimethyl sulfoxide , hexamethylphosphoramide, sulfolane, dimethylacetamide, and polar aprotic solvents such as N-methylpyrrolidone or the like, or two or more.

Reaction [B] can be performed normally at 0-120 degreeC, Preferably it can carry out at 20-80 degreeC. The reaction time is usually about 0.5 to 24 hours, preferably about 1 to 12 hours.

The compound of the above formula (IV) is a known compound, or can be prepared according to known information. For example, the compound of formula (IV) can be prepared according to Org. .

The compounds of the above formula (V) include novel compounds. This compound can be produced according to Gabriel's method, for example, according to the following reaction [C].

[chemical 4]

In reaction [C], A is as described above, and T is halogen, -OSO ₂ G (G is a sulfonate residue) or -OH. When T is halogen or -OSO ₂ G, M is sodium or potassium, and when T is -OH, M is a hydrogen atom. Examples of the sulfonate residue include C _1-6 alkyl groups such as methyl and ethyl groups; phenyl groups that may be substituted by C _1-6 alkyl groups; and the like.

When T is halogen or -OSO ₂ G and M is sodium or potassium, the first step of the reaction [C] can usually be performed in the presence of a solvent.

As the solvent, any solvent may be used as long as it is inert to the reaction. For example, ethers such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane, and dimethoxyethane; aromatic hydrocarbons such as benzene, toluene, and xylene; acetonitrile, propionitrile, N, Polar aprotic solvents such as N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoramide, sulfolane, dimethylacetamide, N-methylpyrrolidone; methanol, ethanol, propanol, n-butanol 1 or more of alcohols such as , tert-butanol, and the like.

When T is halogen or -OSO ₂ G and M is sodium or potassium, the first step of the reaction [C] can be performed usually at 0 to 150°C, preferably at 30 to 110°C. The reaction time is usually about 0.5 to 24 hours, preferably about 1 to 12 hours.

When T is -OH and M is a hydrogen atom, the first step of the reaction [C] is usually carried out according to the Mitsunobu method. For example, it can be performed using dialkyl azodicarboxylate and triphenylphosphine in the presence of a solvent. The above-mentioned dialkyl azodicarboxylate and triphenylphosphine are usually used at an equimolar level with respect to the compound of the formula (VI). As said dialkyl azodicarboxylate, diethyl azodicarboxylate, diisopropyl azodicarboxylate, etc. are mentioned, for example.

As the solvent, any solvent may be used as long as it is inert to the reaction. For example, ethers such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane, and dimethoxyethane; chlorobenzene, dichlorobenzene, methylene chloride, chloroform, carbon tetrachloride, dichloromethane, One or more of halogenated hydrocarbons such as ethane, trichloroethane, and dichloroethylene; and aromatic hydrocarbons such as benzene, toluene, and xylene.

When T is -OH and M is a hydrogen atom, the first step of the reaction [C] is usually carried out at 0 to 80°C, preferably at 20 to 60°C. The reaction time is usually about 0.5 to 24 hours, preferably about 1 to 16 hours.

The second step of the reaction [C] can usually be carried out by decomposing the compound of the formula (VIII) using hydrazine in the presence of a solvent. The above-mentioned hydrazines can usually be used at an equimolar level relative to the compound of formula (VIII).

As the solvent, any solvent may be used as long as it is inert to the reaction. For example, ethers such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane, and dimethoxyethane; aromatic hydrocarbons such as benzene, toluene, and xylene; methanol, ethanol, propanol, One or two or more of alcohols such as n-butanol and tert-butanol.

The second step of reacting [Cl] can usually be carried out at 0 to 140°C, preferably at 30 to 100°C. The reaction time is usually about 0.5 to 24 hours, preferably about 2 to 12 hours.

Preferred forms of pest control agents containing the compound of the present invention are as follows. The pest control agent containing the compound of the present invention is used, for example, as a control agent for various pests that are problematic in the field of agriculture and horticulture, that is, a pest control agent for agriculture and horticulture, or as a control agent for pests parasitic on animals, that is, an animal Parasite control agents are particularly useful.

As an agricultural and horticultural pest control agent, for example, it is useful as an insecticide, acaricide, nematicide, and soil insecticide, and specifically, it is useful for preventing and controlling spider mite, red spider mite, Kansawa spider mite, citrus Plant parasitic mites such as panonychia, apple panonychia, tarsus polyphagophagous, orange spiny gall mite, calla root mite, etc.; diamondback moth, cabbage armyworm, litura, codling moth, cotton bollworm , Tobacco moth, Tobacco moth, Rice vertical leaf roller, Cotton brown belt tortrix, Apple small tortrix, Peach heart-eating moth, Pear small cutworm, Small cutworm, Yellow cutworm, Potato leaf beetle, Yellow Shougua, Mexico Cotton boll weevils, aphids, planthoppers, cotton leaf collembola, scale insects, stinkbugs, whiteflies, thrips, locusts, flower flies, scarabs, ants, liriomyza, etc. Agricultural pests; plant parasitic nematodes such as root-knot nematodes, heterodermal nematodes, root spot nematodes, rice stem apex nematodes, strawberry bud nematodes, pine wood nematodes, etc.; gastropods such as slugs and strong snails; Soil pests such as isopods, woodworms, etc.; hygienic pests such as poultry mite, housefly, Culex, cockroaches, etc.; It is effective in the control of house pests; clothing and house pests such as bag clothing moth, carpet rot, and house termites; indoor dust mites such as tyrophagous tyrophagous, dust mites, and clawed mites. Among them, the agricultural and horticultural pest control agent containing the compound of the present invention is particularly effective for controlling plant parasitic mites, agricultural pests, plant parasitic nematodes and the like. In addition, the agricultural and horticultural pest control agent containing the compound of the present invention is also effective for controlling various pests resistant to agents such as organophosphorus agents, carbamate agents, and synthetic pyrethrin agents. Furthermore, since the compound of the present invention has excellent penetrability and transferability, by treating the soil with an agricultural and horticultural pest control agent containing the compound of the present invention, it is effective in controlling soil harmful insects, mites, nematodes, gastropods, etc. It can also control the pests in the stem and leaf while keeping the foot.

Other preferred forms of pest control agents containing the compound of the present invention include agricultural and horticultural products for comprehensively controlling the above-mentioned plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods, soil pests, etc. pest control agent.

The agricultural and horticultural pest control agent containing the compound of the present invention is usually mixed with the compound and various adjuvants on pesticides to form powder, granule, granule wettable powder, wettable powder, aqueous suspension, oily suspension, water Solvents, emulsions, liquids, pastes, aerosols, microsprays, etc., can be used in various forms of preparations, but as long as they are suitable for the purpose of the present invention, all preparation forms commonly used in this field can be used. Examples of auxiliary agents used in formulations include diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, a mixture of kaolinite and sericite, clay, sodium carbonate, baking soda, mirabilite, zeolite, starch Solid carrier such as water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N, N - Solvents of dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, alcohol, etc.; fatty acid salts, benzoates, alkyl sulfosuccinates, dialkyl sulfosuccinates salt, polycarboxylate, alkyl sulfate, alkyl sulfate, alkyl aryl sulfate, alkyl diglycol ether sulfate, alcohol sulfate, alkyl sulfonate, alkyl aryl Sulfonate, aryl sulfonate, lignosulfonate, alkyl diphenyl ether disulfonate, polystyrene sulfonate, alkyl phosphate salt, alkyl aryl phosphate, styryl aryl Phosphates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl aryl ether sulfates, polyoxyethylene alkyl aryl ether sulfates, polyoxyethylene alkyl ether phosphates, polyoxyethylene alkanes Anionic surfactants or developing agents such as aryl phosphate ester salts and naphthalenesulfonic acid formaldehyde condensate salts; sorbitan fatty acid esters, glycerin fatty acid esters, fatty acid polyglycerides, fatty acid alcohol polyglycols Ether, acetylene glycol, acetylene alcohol, alkylene oxide block polymer, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene styryl aryl ether, polyoxyethylene glycol alkyl Nonionic such as ether, polyethylene glycol, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hardened castor oil, polyoxypropylene fatty acid ester Surfactants and spreaders; olive oil, guawa kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, groundnut oil, cottonseed oil, soybean oil, rapeseed oil, Vegetable oils such as linseed oil, tung oil, and liquid paraffin, or mineral oils. As long as the various components of these auxiliary agents do not deviate from the object of the present invention, one type or two or more types may be appropriately selected and used. In addition, other than the above-mentioned adjuvants, it may be appropriately selected and used from those known in the art. Various auxiliary agents such as bulking agents, thickeners, anti-settling agents, antifreezing agents, dispersion stabilizers, phytotoxicity reducing agents, antifungal agents and the like can also be used. The compounding ratio of the compound of the present invention and various auxiliary agents is 0.001:99.999 to 95:5, preferably 0.005:99.995 to 90:10. In actual use, such preparations may be used as they are, or diluted to a predetermined concentration with a diluent such as water, and then used by adding various developing agents (surfactant, vegetable oil, mineral oil, etc.) as necessary.

The application of the agricultural and horticultural pest control agent containing the compound of the present invention varies according to the weather conditions, preparation form, application period, application site, type or occurrence of pests and diseases. The active ingredient concentration is 800000ppm, preferably 0.5-500000ppm, and the application amount per unit area is 0.05-50000g, preferably 1-30000g, of the compound of the present invention per 1 hectare. In addition, the application of the agricultural and horticultural pest control agent as another preferred embodiment of the pest control agent containing the compound of the present invention can be performed in accordance with the application of the above-mentioned pest control agent. The present invention also includes methods for controlling pests using such an application method, particularly methods for controlling plant parasitic mites, agricultural pests, and plant parasitic nematodes.

The various formulations of agricultural and horticultural pest control agents containing the compound of the present invention, or their dilutions, can usually be applied by the generally performed application methods, namely spreading (such as spreading, spraying, spraying (misting), atomizing (atomizing) , spraying, water surface application, etc.), soil application (mixing, pouring, etc.), surface application (coating, powder coating, covering, etc.), impregnation of poison baits, etc. In addition, mixing the above active ingredients into feed and administering to livestock can also inhibit the occurrence and growth of pests, especially harmful insects, in their excrement. Alternatively, the so-called ultra low volume application can be used. In this method, 100% active ingredient may be contained.

In addition, the pest control agent for agriculture and horticulture containing the compound of the present invention can be mixed or used in combination with other pesticides, fertilizers, phytotoxicity mitigating agents, etc., and in such cases, more excellent effects and actions can be exhibited. Examples of other agricultural chemicals include herbicides, insecticides, acaricides, nematocides, soil insecticides, fungicides, antiviral agents, attractants, antibiotics, plant hormones, and plant growth regulators. In particular, a mixed pest control composition in which the compound of the present invention is mixed or used in combination with one or more active ingredient compounds of other pesticides can improve the scope of application, period of chemical treatment, control activity, etc. . In addition, the compound of the present invention and other active ingredient compounds of agricultural chemicals may be mixed and used in the preparations prepared separately, or both may be prepared and used together. The present invention also encompasses such mixed pest control compositions.

The mixing ratio of the compound of the present invention and the active ingredient compound of other pesticides varies according to the weather conditions, preparation form, application period, application site, type or occurrence of pests and diseases, and cannot be determined uniformly, but is generally 1: 300-300:1, preferably 1:100-100:1. In addition, the suitable amount for application is 0.1 to 50000 g, preferably 1 to 30000 g, as the total active ingredient compound amount per 1 hectare. The present invention includes a pest control method using such a mixed pest control composition application method.

Insecticides, acaricides, nematocides, or soil insecticides among the above-mentioned other pesticides, that is, active ingredient compounds (common names; including a part of the application) of pest control agents include, for example, profenofos (Profenofos), Dichlorvos (Dichlorvos), Fenamiphos, Fenitrothion, Phenthion (EPN), Diazinon, Chlorpyrifos-methyl, Acetylform Acephate, Prothiofos, Fosthiazate, Phosphocarb, Cadusafos, Dislfoton, Chlorpyrifos, Demeton-S -methyl), dimethoate (Dimethoate), methamidophos (Methamidophos), parathion (Parathion) and other organic phosphate compounds;

Carbaryl, Propoxur, Aldicarb, Carbofuran, Thiodicarb, Methomyl, Oxamyl, Ethylsulfur Carbamate compounds such as Ethiofencarb, Pirimicarb, Fenobucarb, Carbosulfan, and Benfuracarb;

Nereistoxin derivatives such as Cartap, Thiocyclam and Bensultap;

Organochlorine compounds such as Dicofol, Tetradifon and Endosulfan;

Organometallic compounds such as fenbutatin oxide;

Fenvalerate, Permethrin, Cypermethrin, Deltamethrin, Cyhalothrin, Tefluthrin, Ethofenprox ), pyrethroid compounds such as Fenpropathrin and Bifenthrin;

Diflubenzuron, Chlorfluazuron, Teflubenzuron, Flufenoxuron, Lufenuron, Novaluron, Bistrifluron Benzoylurea compounds such as Noviflumuron;

Youth hormone-like compounds such as Methoprene, Pyriproxyfen, and Fenoxycarb;

Pyridazinone compounds such as Pyridaben;

Pyrazole compounds such as Fenpyroximate, Fipronil, Tebufenpyrad, Ethiprole, Tolfenpyrad, Acetoprole, Pyrafluprole, and Pyriprole;

Imidacloprid, Nitenpyram, Acetamiprid, Thiacloprid, Thiamethoxam, Clothianidin, Dinotefuran, etc. nicotine;

Tebufenozide, Methoxyfenozide, Chromafenozide, Halofenozide and other hydrazine compounds;

Dinitro compounds, organosulfur compounds, urea compounds, triazine compounds, hydrazone compounds, or other compounds include flonicamid, buprofezin, hexythiazox ( Hexythiazox), Amitraz, Chlordimeform, Silafluofen, Triazamate, Pymetrozine, Pyrimidifen, Chlorfenapyr ( Chlorfenapyr), Indoxacarb, Acequinocyl, Etoxazole, Cyromazine, 1,3-dichloropropene, Acequinocyl (Diafenthiuron), Benclothiaz, Flufenerim, Pyridalyl, Spirodiclofen, Bifenazate, Spiromesifen, Propargite, Tetramite Compounds such as Clofentezine, Fluacrypyrim, Flubendiamide, Cyflumetofen, Metaflumizone, and Amidoflumet. Furthermore, it is also possible to mix and use microbial pesticides such as BT agent, entomopathogenic virus agent, entomopathogenic filamentous fungal agent, nematode pathogenic filamentous fungal agent, etc.; Antibiotics such as Emamectin-Benzoate, Milbemectin, Spinosad, Ivermectin, and Lepimectin; natural products such as Azadirachtin and Rotenone, and the like.

Examples of the active ingredient compound (common name; including some pending applications) of fungicides among the above-mentioned other agricultural chemicals include Mepanipyrim, Pyrimethanil, and Cyprodinil. pyrimethamine compounds;

Triadimefon, Bitertanol, Triflumizole, Etaconazole, Propiconazole, Penconazole, Flusilazole , Myclobutanil, Cyproconazole, Terbuconazole, Hexaconazole, Furconazole-cis, Prochloraz, Metconazole ), Epoxiconazole, Tetraconazole, Oxpoconazole, Sipconazole and other nitrogen compounds;

Quinoxaline compounds such as Quinomethionate;

Dithiocarbamate compounds such as Maneb, Zineb, Mancozeb, Polycarbamate, and Propineb;

Organochlorine compounds such as Fthalide, Chlorothalonil, and Quintozene;

Imidazole compounds such as Benomyl, Thiophanate-Methyl, Carbendazim, and Cyazofamid;

Pyridinamine compounds such as Fluazinam;

Cymoxanil, a cyanoacetamide compound;

Metalaxyl, Oxadixyl, Ofurace, Benalaxyl, Furalaxyl, Cyprofuram, and such phenylamide compounds;

sulfenic acid compounds such as Dichlofluanid;

Copper compounds such as Cupric hydroxide and Oxine Copper;

Isoxazole compounds such as Hydroxyisoxazole;

Fosetyl-Al, Tolcofos-Methyl, S-Benzyl O, O-Diisopropyl Phosphorothioate, O-Ethyl S, S-Diphenyl Disulfide Organophosphorus compounds such as phosphonate and aluminum ethylhalophosphate;

N-halothioalkyl compounds such as Captan, Captafol, and Folpet;

Dicarboimide compounds such as Procymidone, Iprodione and Vinclozolin.

Benzoanilide compounds such as Flutolanil, Mepronil, and Zoxamid;

Piperazine compounds such as Triforine;

Pyridine compounds such as Pyrifenox;

Methanol compounds such as Fenarimol and Flutriafol;

Piperidine compounds such as fenpropidine;

Morpholine compounds such as Fenpropimorph;

Organotin compounds such as triphenyltin hydroxide (Fentin Hydroxide) and triphenyltin acetate (FentinAcetate);

Urea compounds such as Pencycuron;

Cinnamic acid compounds such as Dimethomorph;

Phenyl carbamates such as Diethofencarb;

Cyanopyrrole compounds such as Fludioxonil and Fenpiclonil;

Azoxystrobin, Kresoxim-Methyl, Metominofen, Trifloxystrobin, Picoxystrobin, Pyraclostrobin, such Imine bacteria (strobilurin) compounds;

Oxazolidinones such as Famoxadone;

Thiaazole amides such as Ethaboxam;

Silthiopham (Silthiopham) such as silylamide compounds;

Amino acid amide carbamate compounds such as Iprovalicarb;

imidazoline compounds such as Fenamidone;

Hydroxyaniline compounds such as Fenhexamid;

Benzenesulfonamide compounds such as Flusulfamid;

Anthraquinone compounds; crotonic acid compounds; as antibiotics or other compounds, Isoprothiolane, Tricyclazole, Pyroquilon, Diclomezine, Allyl Probenazole, Quinoxyfen, Propamocarb Hydrochloride, Spiroxamine, Chloropicrin, Dazomet, Metabam ( Metam-sodium) and so on.

In addition, as pesticides that can be mixed or used in combination with the compound of the present invention, there are, for example, active ingredient compounds of herbicides described in "Agrochemical Handbook" (Farm Chemicals Handbook, 2002 edition), especially soil treatment-type compounds.

As an animal parasite control agent, for example, for ectoparasites parasitic on the body surface (back, armpit, lower abdomen, inner crotch, etc.) Liver, blood vessels, subcutaneous tissue, lymphatic tissue, etc.) are effective in the prevention and control of internal parasites, and among them, it is effective in the control of external parasites.

Examples of external parasites include zoonotic mites, fleas, and the like. There are so many such types that it is difficult to list them all, here is one example.

Examples of animal parasitic mites include 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, Dermacentor taiwanesis and other hard ticks; Dermanyssus gallinae, Ornithonyssus sylviarum, Wood poultry thorn mites such as Ornithonyssus bursa, Eutrombicula wichmanni, Leptotrombidium akamushi, Leptotrombidium pallidum, Leptotrombidium fuji, Leptotrombidium tosa, Neotrombicula autumnalis, Eutrombicula alfredduge Chiggers such as Heleniculamiyagawai; carnivorous mites such as Cheyletiella yasguri, Cheyletiella parasitivorax, Cheyletiella blakei; Psoroptes cuniculi, Chorioptes bovis, dogs and cats Scabies such as ear mite (Otodectes cynotis), scabies mite (Sarcoptes scabiei), and cat back anal mite (Notoedres cati); Demodex mite such as dog demodex (Demodex canis), etc. Among them, the animal parasite control agent containing the compound of the present invention is particularly effective against hard ticks and the like.

Examples of fleas include external parasitic wingless insects belonging to the order Siphonaptera, and more specifically fleas belonging to the family Pulicidae and the family Ceratephyllus. As fleas belonging to the family Flea, for example, Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Echidnophaga gallinacea, Xenopsylla cheopis ), Leptopsylla segnis, Nosopsyllus fasciatus, Monopsyllus anisus, etc. Among them, the agent for controlling animal parasites containing the compound of the present invention is effective for controlling fleas belonging to the family Pleidae, particularly Ctenocephalis canis, Ctenocephalic felis, and the like.

Examples of other external parasites include lice such as bovine blind lice, horse blood-sucking lice, sheep lice, long-nosed bull lice, and head lice; biting lice such as dog-biting lice; Diptera pests, etc. In addition, examples of internal parasites include nematodes such as lungworms, whipworms, strong nematodes, gastric parasites, roundworms, and filarials; Tapeworms such as foramen, polycephala, Taenia polycysticum, and polycystic tapeworm; flukes such as Schistosoma japonicum and Fasciola japonicum; protozoa such as coccidia, Plasmodium, intestinal sarcocystis, toxoplasma gondii, and cryptosporidium wait.

Examples of host animals include various pets, domestic animals, and poultry, and more specifically, dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (such as pigeons, etc.) , parrot, Jiuguan bird, munia, parrot, white-rumped munia, canary, etc.) cattle, horses, pigs, sheep, ducks, chickens, etc. Among them, the agent for controlling animal parasites containing the compound of the present invention is effective for controlling harmful organisms parasitic on pets or domestic animals, especially ectoparasites. Among pets or livestock it is especially effective on dogs, cats, cows or horses.

When the compound of the present invention is used as an animal parasite control agent, it can be used directly, or formulated together with appropriate auxiliary agents into powder, granule, tablet, powder, capsule, liquid, emulsion, aqueous suspension, oily suspension etc. in various forms. In addition, other than the above-mentioned formulation forms, any formulation form commonly used in this field may be used as long as it is suitable for the purpose of the present invention. As the adjuvant used in the formulation, anionic surfactants or nonionic surfactants exemplified as the adjuvant for the formulation of the above-mentioned agricultural and horticultural pest control agent; Cationic surfactants such as ammonium bromide; water, acetone, acetonitrile, monomethylacetamide, dimethylacetamide, dimethylformamide, 2-pyrrolidone, N-methyl-2-pyrrolidone, Kerosene, Triacetone, Methanol, Ethanol, Isopropanol, Benzyl Alcohol, Ethylene Glycol, Propylene Glycol, Polyethylene Glycol, Liquid Polyoxyethylene Glycol, Butyl Diethylene Glycol, Ethylene Glycol Monomethyl Ether, Ethylene Glycol Solvents such as monoethyl ether, diethylene glycol monoethyl ether, diethylene glycol n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol n-butyl ether; butyl hydroxyanisole, butyl hydroxytoluene, ascorbic acid, metabio Antioxidants such as sodium bisulfate, propyl gallate, and sodium thiosulfate; film-forming agents such as copolymers of polyvinylpyrrolidone, polyvinyl alcohol, vinyl acetate, and vinylpyrrolidone; as the above-mentioned agricultural and horticultural Vegetable oil or mineral oil as exemplified auxiliary agents for the preparation of harmful organism control agents; carriers such as lactose, sucrose, glucose, starch, flour, corn flour, soybean oil meal, defatted rice bran, calcium carbonate, other commercially available feed ingredients, and the like. As long as the purpose of the present invention is not deviated from the various components of these auxiliary agents, one type or two or more types may be appropriately selected and used. In addition, those known in the field other than the above-mentioned adjuvants may be appropriately selected and used, and further, various adjuvants used in the above-mentioned agricultural and horticultural fields and the like may be appropriately selected and used.

The compounding ratio of the compound of the present invention and various auxiliary agents is usually about 0.1:99.9 to 90:10. When actually using these preparations, they can be used as they are, or diluted to a predetermined concentration with a diluent such as water, and then used by adding various developing agents (surfactant, vegetable oil, mineral oil, etc.) as needed.

The compounds of the present invention can be administered to a host animal orally or parenterally. Examples of oral administration methods include methods of administering tablets, liquids, capsules, pancakes, biscuits, minced meat, and other feeds containing the compound of the present invention. Examples of parenteral administration methods include, for example, methods in which the compound of the present invention is formulated into an appropriate preparation and injected into the body by intravenous injection, intramuscular administration, intradermal administration, or subcutaneous administration; (spot-on), pour-on, spray treatment, etc. to administer to the body surface; method of embedding a resin sheet or the like containing the compound of the present invention under the skin of the host animal, etc.

The dose of the compound of the present invention to the host animal varies depending on the method of administration, the purpose of administration, the symptoms of the disease, etc., but it is usually administered at a ratio of 0.01 mg to 100 g, preferably 0.1 mg to 10 g, relative to 1 Kg body weight of the host animal. medicine is appropriate.

The present invention also includes methods of controlling pests, particularly methods of controlling ectoparasites or endoparasites, based on the above-mentioned administration method or dosage.

In addition, in the present invention, various diseases of the host animal caused by the above-mentioned control of animal parasitic harmful organisms may be prevented or treated. Thus, the present invention also includes a prophylactic or therapeutic agent for animal diseases caused by parasitic animals, and a method for preventing or treating animal diseases caused by parasitic animals, which contain the compound of the present invention as an active ingredient.

When the compound of the present invention is used as an animal parasite control agent, it can be mixed with auxiliary agents or used in combination with various vitamins, minerals, amino acids, nutrients, enzyme preparations, antipyretics, sedatives, anti-inflammatory agents, bactericidal agents, etc. Agents, colorants, fragrances, preservatives, etc. In addition, various other animal drugs or pesticides can be mixed or used in combination according to needs, such as insect repellents, anticoccidials, insecticides, acaricides, fleaicides, nematocides, fungicides, antibacterials, etc. In such a case, a more excellent effect may be exhibited. The present invention includes a mixed pest control composition using the above various components in combination or in combination, and also includes a pest control method using the composition, particularly a method for controlling ectoparasites or endoparasites.

Some preferred forms of the compounds of the present invention are exemplified below. Among the illustrated aspects, any two or more of the following (1) to (8) can be appropriately combined, and compounds based on this combination are also preferred aspects of the compound of the present invention. In addition, pest control agents containing the following compounds as active ingredients, agricultural and horticultural pest control agents, insecticides, acaricides or nematicides, animal parasite control agents, animal ectoparasite control agents, parasites A preventive or therapeutic agent for the induced animal disease is also a preferred aspect of the present invention. In addition, a method of controlling harmful organisms by administering an effective amount of the following compounds is also a preferred aspect of the present invention. However, the present invention is not limited thereto.

(1) A compound of the above formula (I) in which at least one of R ¹ is substituted at the 4-position, and the R ¹ is a fluorine atom or a chlorine atom.

(2) A compound of the above formula (I) in which at least one of R ¹ is substituted at the 4-position, and the R ¹ is a chlorine atom.

(3) At least one of R ¹ is substituted at the 4-position, and the R ¹ is alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy A compound of the above-mentioned formula (I) having a radical, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, phenoxycarbonyl which may be substituted, nitro or formyl.

(4) Compounds of the above formula (I) in which R ² is halogen, haloalkyl, or haloalkoxy.

(5) A compound of the above formula (I) in which R ³ is halogen.

(6) The compound of the above-mentioned formula (I) in which R ³ is halogen and is 3- or 5-monosubstituted or 3,5-disubstituted.

(7) A compound of the above formula (I) in which Y is cyclopropyl.

(8) The compound of the above formula (I) in which Y is a cyclopropyl group and the cyclopropyl group is substituted with 1 to 5 substituents selected from the group consisting of halogen, alkyl and haloalkyl.

(9) ^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 a cyclopropyl group 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. The compound of the above formula (I).

(10) The compound described in (9) above in which R ¹ is 2-monosubstituted or 2,4-disubstituted, and R ¹ is 3-monosubstituted.

(11) 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; A compound of the above formula (I) wherein n is 0; q is 1.

(12) The compound described in (11) above in which R ¹ is 2,4-disubstituted and R ³ is 3-monosubstituted.

(13) The compound described in the above (12) in which R ¹ at the 4th position is a chlorine atom.

(14) Formula (I) is formula (I-1), and R ^1a is halogen or alkyl; R ^1b and R ^1d are hydrogen atoms respectively; R ^1c is alkyl, halogenated alkyl, alkenyl, halogenated chain Alkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, optionally substituted phenoxycarbonyl, nitro or methyl Acyl; R ₂ is halogen, haloalkyl or haloalkoxy; R ^3a is halogen or haloalkyl; R ^3b , R ^3c and R ^3d are hydrogen atoms; A is an alkyl group substituted by Y; Y can be selected from A cyclopropyl group substituted by 1 to 5 substituents in the group consisting of halogen, alkyl and haloalkyl; the compound where n is 0.

[chemical 5]

(15) The compound described in (14) above, wherein R ^1c is a haloalkyl group, an alkylcarbonyl group or a formyl group.

(16) The compound described in (14) above, wherein R ^1c is a haloalkyl group.

(17) The compound described in the above (14) in which Y is cyclopropyl.

(18) Formula (I) is formula (Ia), and R ¹ is halogen or alkyl; R ² and R ³ are halogen or -CF ₃ respectively; A is alkyl substituted by Y; Y is halogen or Alkyl-substituted C3-4 cycloalkyl; m is 1 or 2; n is 0 compound.

[chemical 6]

(19) Formula (I) is the above formula (Ia), and R ¹ is halogen or alkyl; R ² and R ³ are independently halogen or -CF ₃ ; A is -XY; X is alkylene; Y is C3-4 cycloalkyl which may be substituted by halogen or alkyl; m is 1 or 2; n is 0 or 1 compound.

Example

Examples of the present invention will be described below, but the present invention is not limited thereto. First, synthesis examples of the compounds of the present invention will be described.

Synthesis Example 1

N-[6-[[(cyclopropylmethyl)amino]carbonyl]-2-methylphenyl]-1-(3-chloro-2-pyridyl)-3-(trifluoromethyl)-1H- Synthesis of pyrazole-5-carboxamide (Compound No.1 mentioned later)

To a mixed solution of 0.8 g of cyclopropylmethylamine hydrochloride and 40 ml of tetrahydrofuran, 1.49 g of triethylamine was slowly added dropwise under ice-cooling, followed by stirring at room temperature for 30 minutes. Then slowly add 1 g of 2-[1-(3-chloro-2-pyridyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-8-methyl-4H-3 , a mixture of 1-benzoxazin-4-one and 10ml tetrahydrofuran. After the dropwise addition was terminated, the mixed solution was reacted under reflux for 4 hours. After the reaction was completed, the solvent was distilled off under reduced pressure, and ethyl acetate and water were added to the residue for extraction. The organic layer was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled off 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 target compound having a melting point of 199.4°C.

Synthesis example 2

N-[4-chloro-2-methyl-6-[[α-methyl-(cyclopropylmethyl)amino]carbonyl]-phenyl]-3-(trifluoromethyl)-1-(3- Synthesis of Chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (compound No.3 mentioned later)

To a mixed solution of 0.82 g of α-methyl-cyclopropylmethylamine hydrochloride and 40 ml of tetrahydrofuran, 1.37 g of triethylamine was slowly added dropwise under ice-cooling, followed by stirring at room temperature for 30 minutes. Then slowly add 1g of 2-[1-(3-chloro-2-pyridyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-6-chloro-8-methyl -A mixture of 4H-3,1-benzoxazin-4-one and 10ml tetrahydrofuran. After the dropwise addition was terminated, the mixed solution was reacted under reflux for 4 hours. After the reaction was completed, the solvent was distilled off under reduced pressure, and ethyl acetate and water were added to the residue for extraction. The organic layer was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1) to obtain 0.45 g of the target compound having a melting point of 210.0°C.

Synthesis example 3

N-[4-chloro-2-methyl-6-[[α-methyl-(cyclopropylmethyl)amino]carbonyl]-phenyl]-3-bromo-1-(3-chloro-2-pyridine base)-1H-pyrazole-5-carboxamide (compound No.9 described later)

To a mixed solution of 0.65 g of α-methyl-cyclopropylmethylamine hydrochloride and 40 ml of tetrahydrofuran, 1.07 g of triethylamine was slowly added dropwise under ice-cooling, followed by stirring at room temperature for 30 minutes. Then slowly add 0.8g of 2-[3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazol-5-yl]-6-chloro-8-methyl-4H-3 , a mixture of 1-benzoxazin-4-one and 10ml tetrahydrofuran. After the dropwise addition was terminated, the mixed solution was reacted under reflux for 4 hours. After the reaction was completed, the solvent was distilled off under reduced pressure, and ethyl acetate and water were added to the residue for extraction. The organic layer was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate = 1/1) to obtain 0.33 g of the target compound having a melting point of 183.6°C.

Synthesis Example 4

N-[2-bromo-4-chloro-6-[[α-methyl-(cyclopropylmethyl)amino]carbonyl]-phenyl]-3-bromo-1-(3-chloro-2-pyridyl Synthesis of )-1H-pyrazole-5-carboxamide (Compound No.15 mentioned later)

To a mixed solution of 0.6 g of α-methyl-cyclopropylmethylamine hydrochloride and 40 ml of tetrahydrofuran, 1 g of triethylamine was slowly added dropwise under ice-cooling, followed by stirring at room temperature for 1 hour. Then slowly drop 0.85g of 2-[3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazol-5-yl]-6-chloro-8-bromo-4H-3, A mixture of 1-benzoxazin-4-one and 10 ml tetrahydrofuran. After the dropwise addition was terminated, the mixed solution was reacted under reflux for 4 hours. After the reaction was completed, the solvent was distilled off under reduced pressure, and ethyl acetate and water were added to the residue for extraction. The organic layer was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate = 1/2) to obtain 0.7 g of the target compound having a melting point of 260.6°C.

Representative examples of the compounds of the present invention represented by the above-mentioned formula (I) are listed in Table 1 below. These compounds can be synthesized according to the above-mentioned synthesis examples or various production methods of the above-mentioned compounds of the present invention.

In Table 1, No. represents the serial number of the compound. In addition, in Table 1, Me represents a methyl group, Et represents an ethyl group, iPr represents an isopropyl group, CPr represents a cyclopropyl group, CBu represents a cyclobutyl group, and Ph represents a phenyl group. In addition, in Table 1, A1 represents -CH ₂ -[CPr], A2 represents -CH(Me)-[CPr], A3 represents -CH ₂ -[2-Me-CPr], A4 represents -CH ₂ -[2 , 2-Cl ₂ -1-Me-CPr], A5 represents -CH ₂ -[1-Me-CPr], A6 represents -CH(Me)-[CBu]. In addition, in Table 1, 2-Me-CPr represents a cyclopropyl group substituted with a methyl group at the 2-position, CO ₂ Ph(4-Cl) represents a phenoxycarbonyl group substituted with a chlorine atom at the 4-position of a phenyl group, and other similar descriptions start with This shall prevail.

In addition, in Table 1, unless otherwise stated, n is 0.

Table 1 no R ^1a R ^1b R ^1C R ^1d R ^{2 R3a} R ^3b R ^3C R ^3d A Physical properties (melting point ℃) 1 Me h h h CF ₃ Cl h h h A1 199.4 2 Me h Cl h CF ₃ Cl h h h A1 216.4 3 Me h Cl h CF ₃ Cl h h h A2 210.0 4 Me h Cl h CF ₃ Cl h h h A3 5 Me h Cl h CF ₃ Cl h h h A4 219.3 6 Me h Cl h Cl Cl h h h A1 7 Me h Cl h Br Cl h h h A1 8 Me h Cl h Cl Cl h h h A2 186.7 9 Me h Cl h Br Cl h h h A2 183.6 10 Me h Cl h CF ₃ Cl h h h A5 161.2 11 Br h Cl h CF ₃ Cl h h h A2 158.2 12 I h Br h CF ₃ Cl h h h A2 145.5 13 Me h Cl h CF ₃ Cl h h h A2 230.9 14 Cl h Cl h CF ₃ Cl h h h A2 238.8 15 Cl h Cl h Br Cl h h h A2 236.8 16 Br h Cl h Br Cl h h h A2 260.6 17 I h Cl h Br Cl h h h A2 251.4 18 Br h f h CF ₃ Cl h h h A2 220.1 19 I h Cl h CF ₃ Cl h h h A2 241.0 20 Cl h f h CF ₃ Cl h h h A2 214.0 twenty one I h 1 h CF ₃ Cl h h h A2 251.9 twenty two Br h f h Br Cl h h h A2 219.2 twenty three Me h Cl h CF ₃ Br h h h A2 162-164 twenty four Me h Cl h Cl CF ₃ h h h A2 154-156 25 Me h Cl h Br Br h h h A2 128-132 26 Cl h f h Br Cl h h h A2 27 I h f h Br Cl h h h A2 28 f h Cl h Br Cl h h h A2 29 f h Cl h CF ₃ Cl h h h A2 30 I h f h CF ₃ Cl h h h A2 31 f h f h CF ₃ Cl h h h A2 32 f h f h Br Cl h h h A2 33 Me h f h CF ₃ Cl h h h A2 34 Me h f h Br Cl h h h A2 35 Me h CO ₂ Me h Br Cl h h h A2 36 Me h CO ₂ -iPr h Br Cl h h h A2

Table 1 (continued) no R ^1a R ^1b R ^1C R ^1d R ^{2 R3a} R ^3b R ^3C R ^3d A Physical properties (melting point ℃) 37 Me h CO ₂ Ph h Br Cl h h h A2 38 Br h Cl h Cl Cl h h h A2 233.2 39 Br h f h Cl Cl h h h A2 179.1 40 Me h _COCH3 h CF ₃ Cl h h h A2 143.4 41 Me h CHO h CF ₃ Cl h h h A2 152.3 42 Me h CHF ₂ h CF ₃ Cl h h h A2 212.9 43 Me h CHF ₂ h Br Cl h h h A2 44 Me h CHF ₂ h Cl Cl h h h A2 45 Et h Cl h CF ₃ Cl h h h A2 215.4 46 Et h Cl h Br Cl h h h A2 47 Et h Cl h Cl Cl h h h A2 48 Me h NO ₂ h CF ₃ Cl h h h A2 197.9 49 Me h NO ₂ h Br Cl h h h A2 50 Me h NO ₂ h Cl Cl h h h A2 51 Me h CF ₃ h Br Cl h h h A2 52 Me h CF ₃ h Cl Cl h h h A2 53 Me h CF ₃ h CF ₃ Cl h h h A2 54 CF ₃ h Cl h Br Cl h h h A2 55 Me h OMe h Br Cl h h h A2 56 Me h OMe h CF ₃ Cl h h h A2 57 Me h OMe h Cl Cl h h h A2 58 OCHF ₂ h Cl h Cl Cl h h h A2 59 OCHF ₂ h Cl h Br Cl h h h A2 60 OCHF ₂ h Cl h CF ₃ Cl h h h A2 61 CHF ₂ h Cl h CF ₃ Cl h h h A2 62 CHF ₂ h Cl h Br Cl h h h A2 63 CHF ₂ h Cl h Cl Cl h h h A2 64 Me h CH= _CH2 h CF ₃ Cl h h h A2 65 Me h C≡CH h CF ₃ Cl h h h A2 66 Me h Cl h CF ₃ Cl h h h A6 67 Me h COCF ₃ h Br Cl h h h A2 68 Me h CH= _CCl2 h CF ₃ Cl h h h A2 69 Me h C≡Cl h CF ₃ Cl h h h A2 70 Me h CO ₂ Ph(4-Cl) h Br Cl h h h A2 71 Me h CO ₂ Ph(4-Me) h CF ₃ Cl h h h A2 72 Me h CO ₂ Ph(4-NO ₂ ) h CF ₃ Cl h h h A2 73 Me h CO ₂ Ph(4-CN) h CF ₃ Cl h h h A2 74 Me h CO ₂ Ph(4-SMe) h CF ₃ Cl h h h A2 75 Et h Cl h OCH ₂ CF ₃ Cl h h h A2 76 Me h NO ₂ h OCH ₂ CF ₃ Cl h h h A2 77 Me h CHF ₂ h CF ₃ h h Cl h A2 78 Et h Cl h Br h h f h A2 79 I h Cl h Br f h f h A2

Table 1 (continued) No. R ^1a R ^1b R ^1C R ^1d R ^{2 R3a} R ^3b R ^3C R ^3d A Physical properties (melting point ℃) 80 I h Cl h Cl Cl h h h A2 220.6 81 Me h Cl h OCH ₂ CF ₃ Cl h h h A2 175.1 82 Br h CHF ₂ h CF ₃ Cl h h h A2 83 Br h CHF ₂ h Br Cl h h h A2 84 Br h CHF ₂ h Cl Cl h h h A2 85 Me h Cl h CF ₃ Cl h Cl h A2 86 Me h Cl h CF ₃ Cl h f h A2 87 Br h NO ₂ h Br Cl h h h A2 88 Br h NO ₂ h CF ₃ Cl h h h A2 89 Br h NO ₂ h Cl Cl h h h A2 90 I h Br h Cl Cl h h h A2 222.9 91 I h Br h Br Cl h h h A2 221.0 92 Me h Me h CF ₃ Cl h h h A2 172.3 93 Me h CO ₂ -iPr h Br Cl h h h A2 176-179 94 Et h Br h CF ₃ Cl h h h A2 175.2 95 Et h NO ₂ h CF ₃ Cl h h h A2 116.8 96 Me h CO ₂ Me h Br Cl h h h A2 190-198 97 CF ₃ h Cl h Br Cl h h h A2 98 CF ₃ h Br h CF ₃ Cl h h h A2 234.8 99 CF ₃ h Cl h CF ₃ Cl h h h A2 230.0 100 Cl h CF ₃ h Br Cl h h h A2 101 Br h CF ₃ h CF ₃ Cl h h h A2 102 Cl h CF ₃ h CF ₃ Cl h h h A2 103 N-oxide of Compound No.1 (n=1) 104 N-oxide of Compound No.3 (n=1) 105 N-oxide of Compound No.9 (n=1) 106 N-oxide of Compound No.16 (n=1) 107 N-oxide of Compound No.22 (n=1) 108 N-oxide of compound No.42 (n=1)

Test examples are described below

Test Example 1 Effect Test on Spodoptera litura

The leaves of cabbage were dipped in the chemical solution prepared with the concentration of the compound of the present invention at 50 ppm or 3.1 ppm for 10 seconds, and then air-dried. Wet filter paper was spread in a Petri dish with a diameter of 9 cm, and the air-dried leaves were placed on it. Put 10 2-3 instar Spodoptera litura larvae on it, cover it and place it in a constant temperature room with lighting. Life and death were judged on the 5th day after releasing the insects, and the death rate was calculated according to the following calculation formula. In addition, anomalous insects are also considered dead. When the mortality rate of 50 ppm was calculated for the above-mentioned compound No.8, 20-22, 25, 41, 91-93 and 96, all the compounds showed a high control effect of more than 90%. In addition, for the above-mentioned compound No.1-3 , 5, 9-19, 23, 24, 38-40, 42, 80, 81 and 90, when the mortality rate of 3.1 ppm was calculated, all the compounds showed a high control effect of 90% or more.

Mortality rate (%)=(number of deaths/number of released insects)×100

Test Example 2 Effect Test on Silver Leaf Whitefly ( Bemisia argentifoli )

In potted cucumbers in which one first true leaf was left and the other leaves were cut off, adults of whitefly was placed and allowed to lay eggs for about 8 hours. Thereafter, it was left to stand in an illuminated constant temperature room at 25° C. for 7 to 10 days. After checking the number of hatched larvae, the parasitic leaves were dipped in a liquid medicine prepared at a concentration of 200 ppm or 50 ppm of the compound of the present invention for about 10 seconds, and then air-dried. After 10-14 days in a constant temperature room with lighting at 25°C, investigate the number of old larvae and pupae, and use the following calculation formula to find out the price. When the control value of 200ppm was calculated for the above-mentioned compound Nos. 11 and 21, a high control effect of more than 80% was shown. In addition, 50ppm was calculated for the above-mentioned compound Nos. 3, 9, 12, 14-20, 22, 38 and 39 All compounds showed a high control effect of more than 80%.

Prevention value (%)=(1-((Ta×Cb)/(Tb×Ca)))×100

Ta: number of old larvae + number of pupae after treatment in the treatment area

Tb: Number of hatched larvae before treatment in the treatment area

Ca: the number of old larvae + the number of pupae after treatment in the no-treatment area

Cb: Number of hatched larvae before treatment in the no-treatment area

Test Example 3 Effect test on green peach aphid ( Myzus persicae )

After the adhesive agent is applied on the petiole of potted eggplant with only one original leaf remaining, 2 to 3 wingless viviparous female adults of green peach aphid are put on the original leaf. After removing the adults 2 days after releasing the insects, the number of larvae was investigated. The eggplant leaves parasitized by the larvae were dipped in a liquid medicine prepared with a concentration of 800 ppm for about 10 seconds, air-dried and then placed in a 25° C. illuminated thermostatic chamber. Five days after the treatment, the number of surviving insects was investigated, and the mortality rate was calculated using the following calculation formula. When the mortality rate was calculated for the above-mentioned compound Nos. 2, 9, 11, 14-18, 20, 22, 23, 38, 39, 42 and 90, all compounds showed a high control effect of 90% or more.

Mortality (%)=(1-(Number of Surviving Insects/Number of Treated Insects))×100

Test Example 4 Effect test on cotton aphid ( Aphis gossypii )

After coating the adhesive agent on the petiole of the potted eggplant with only one original leaf remaining, 3 to 4 apterous viviparous female adults of cotton aphid are placed on the original leaf. Adults were removed 2 days after release, and the number of larvae was investigated. The eggplant leaves parasitized by the larvae were dipped in a liquid medicine prepared with a concentration of 50 ppm of the compound of the present invention for about 10 seconds, air-dried and then placed in a 25° C. illuminated thermostatic chamber. After 5 days of treatment, the number of surviving insects was investigated, and the mortality rate was determined in the same manner as in the above-mentioned Test Example 3. When the mortality rate was calculated for the above compound Nos. 16, 18 and 22, all the compounds showed a high control effect of 90% or more.

Test Example 5 Effect Test on Liriomyza trifolii

In a chemical solution prepared at a concentration of 25 ppm or 12.5 ppm of the compound of the present invention, leaves of kidney beans uniformly producing eggs of Liriomyza cloverii were dipped for about 10 seconds, and then air-dried. Spread the wet filter paper in a plastic cup with a diameter of 9 cm and a height of 4 cm, and place the leaves of the air-dried kidney beans on it. Thereafter, the lid was put on and placed in a 25° C. illuminated constant temperature room. After 6-8 days of treatment, investigate the number of surviving old larvae and pupae, and use the following calculation formula to find out the prevention and removal price. For the above-mentioned compound No.9, 14 and 23, when the control value of 25ppm was calculated, all the compounds showed a high control effect of more than 90%. In addition, for the above-mentioned compound No. When the control value of 12.5 ppm was calculated, all the compounds showed a high control effect of 90% or more.

Control price (%)=(1-((the number of old larvae in the treatment area+the number of pupae)/(the number of old larvae in the area without treatment+the number of pupae)))×100

Test Example 6 Effect Test on Thrips palmi ( Thrips palmi )

Only one first true leaf remained on the potted cucumber and the other leaves were cut off. The remaining leaves were dipped in a solution prepared at a concentration of 50 ppm of the compound of the present invention for about 10 seconds, and then air-dried. Thereafter, the leaves of cucumbers parasitized by 1st instar larvae were placed on the above-mentioned treated leaves. The next day, the leaves of the cucumbers were excised, and the number of larvae transferred to the treated leaves was investigated. Spread the wet filter paper in a plastic cup with a diameter of 9 cm and a height of 4 cm, and place the cut leaves on it. Thereafter, the lid was put on and placed in a 25° C. illuminated constant temperature room. 12 to 15 days after the treatment, the number of surviving insects was investigated, and the prevention and removal were carried out in the same manner as in the above-mentioned Test Example 2. When the above-mentioned compound Nos. 11, 12, 16, 22, 38 and 39 were tested for control and devalence, all compounds showed a high control effect of 90% or more.

Test Example 7 Effect Test on Epilachna vigintioctopunctata

The leaves of the eggplant were dipped in the liquid medicine with the concentration of the compound of the present invention being 25ppm or 12.5ppm for about 10 seconds, and then air-dried. Spread the wet filter paper in a plastic cup with a diameter of 9 cm and a height of 4 cm, and place the leaves of the air-dried eggplant on it. Put five 1st to 2nd instar ladybug larvae on it, cover it and place it in a constant temperature room with lighting at 25°C. On the 4th to 6th day after releasing the insects, life and death were judged, and the death rate was calculated in the same manner as in Test Example 1 above. In addition, anomalous insects are also considered dead. When the mortality rate of 25ppm was calculated for the above-mentioned compound Nos. 9 and 11, all the compounds showed a high control effect of 90% or more. In addition, the mortality rate of 12.5ppm was calculated for the above-mentioned compound Nos. 3, 16, 22, 38 and 39 , all compounds showed a high control effect of more than 90%.

Test Example 8 Effect Test on Housefly ( Musca domestica )

After putting 10 g of bait medium into a plastic cup with a diameter of 6 cm and a height of 3 cm, add 10 ml of a medicinal solution prepared with a concentration of the compound of the present invention at 200 ppm, and mix. Put 20 or 30 hatched 4-day-old larvae, cover and place in a constant temperature room with lighting at 25°C for 15-16 days. Thereafter, the number of adults was checked, and the eclosion suppression rate was calculated using the following calculation formula. When the feathering inhibition rate was calculated for the above-mentioned compound Nos. 3, 9, 11, 12, and 14 to 20, all the compounds showed a high control effect of 90% or more.

Eclosion inhibition rate (%)=(1-(number of adults/number of released insects))×100

Test Example 9 Effect Test on House Termite ( Coptotermes formosanus )

Spread the filter paper in a glass Petri dish with a diameter of 9 cm, and treat it with 1 ml of a drug solution prepared with a concentration of the compound of the present invention at 50 ppm. Thereafter, 10 worker ants and 1 soldier ant of house termites were put in, covered and placed in a 25° C. illuminated constant temperature room. Six days after the treatment, the number of dead worker ants was investigated, and the death rate was calculated using the following calculation formula. When the mortality rate was calculated for the above compound Nos. 3, 9, 11, 12, 14 to 16, and 22, all the compounds showed a high control effect of 90% or more.

Mortality rate (%) = (number of dead worker ants/10) × 100

Test Example 10 Penetration and transferability test of Spodoptera litura

Use 10 ml of the medicinal solution prepared with the compound of the present invention at a concentration of 80 ppm or 200 ppm to treat the roots of potted cabbage at the 5-6 leaf stage. Spread the filter paper in a petri dish with a diameter of 9 cm, and place the cabbage leaves cut after 10 days of treatment. Put 10 2-3 instar Spodoptera litura larvae into it, cover it and place it in an illuminated constant temperature room at 25°C. On the 4th to 5th day after releasing the insects, life and death were judged, and the death rate was calculated in the same manner as in Test Example 1 above. In addition, anomalous bugs are also considered dead. When the mortality rate of 800ppm was calculated for the above-mentioned compound No. 8, all compounds showed a high control effect of 90% or more. In addition, when the mortality rate of 200ppm was calculated for the above-mentioned compound No. 3, 9, 11, 16, 18 and 22 , all compounds showed a high control effect of more than 90%.

Test Example 11 Drug efficacy test on Haemaphysalis longicornis

1 ml of an acetone solution (concentration: 10 μg/ml) of the test compound was dropped to treat a 9 cm diameter petri dish with a micropipette. On the other hand, as a control area, 1 ml of acetone was also drop-treated. After the inner surface of the petri dish is dry, about 100 larvae are placed, covered with a polyethylene sheet and sealed with an elastic band. Thereafter, the petri dish was left still under conditions of a constant temperature of 25° C., a relative humidity of 100%, and constant darkness except during observation. After a certain period of time (5 minutes, 10 minutes, 15 minutes, 20 minutes, 30 minutes, 45 minutes, 1 hour, 2 hours, 4 hours, 6 hours, and 24 hours) after the larvae were placed in the Petri dish Observe and record the number of rolling ticks after exposure to the agent. The above operation was repeated twice.

Use the following Abbott correction formula to correct the roll rate at each observation time, then draw the probability unit-time straight line, and then calculate the half roll time (KT50 value). The KT50 value of each test compound, the above-mentioned compound No.3 is 9 minutes and 8 minutes, the above-mentioned compound No.9 is 7.5 minutes and 6 minutes, and the following comparative compound A is 80 minutes and 40 minutes, the following compound B is 120 minutes and 80 minutes.

Corrected rolling rate (%)=[(non-rolling rate of control area-non-rolling rate of treatment area)/non-rolling rate of control area]×100

Comparative compound A is the following compound as compound 484 in WO03/24222, compound 497 in WO03/15518, and compound 2 in WO03/15519.

[chemical 7]

比较化合物A

Comp A

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

[chemical 8]

比较化合物B

Comp B

Test Example 12 Drug efficacy test on cat fleas ( Ctenocephalides felis )

A glass tube (2.6 cm inner diameter, 5.3 cm ³ bottom area, 12 cm height) with a smooth bottom was subjected to drop treatment with 0.5 ml of an acetone solution of the compound of the present invention prepared at 5.3 ppm. The acetone was allowed to evaporate at room temperature to form a dry film containing the compound of the invention on the underside. 10 adults of cat flea (Ctenocephalides felis) (non-blood-sucking adults within 5 days after eclosion) were placed therein. and expose the compounds of the invention. Experiments were performed in triplicate.

After 48 hours of exposure, the life and death of fleas were judged, and the death rate was determined in the same manner as in Test Example 1 above. When the mortality rate was calculated for the above-mentioned compound No. 16, a high control effect of 90% or more was shown.

Preparation examples are described below.

Preparation Example 1

(1) Compound of the present invention 20 parts by weight

(2) Clay 72 parts by weight

(3) Sodium lignosulfonate 8 parts by weight

Mix the above ingredients evenly to make wettable powder.

Preparation Example 2

(1) Compound of the present invention 5 parts by weight

(2) Talc 95 parts by weight

Mix the above ingredients evenly to make a powder.

Preparation example 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

Mix and dissolve the above ingredients evenly to make an emulsion.

Preparation Example 4

(1) Clay 68 parts by weight

(2) Sodium lignosulfonate 2 parts by weight

(3) Polyoxyethylene alkyl aryl sulfate 5 parts by weight

(4) Micropowdered silica 25 parts by weight

Mix the above ingredients and the compound of the present invention at a weight ratio of 4:1 to prepare a wettable powder.

Preparation Example 5

(1) Compound of the present invention 50 parts by weight

(2) Oxygenated polyalkylphenyl phosphate-triethanolamine 2 parts by weight

(3) Polysiloxane 0.2 parts by weight

(4) Water 47.8 parts by weight

Add further

(5) Sodium polycarboxylate 5 parts by weight

(6) Anhydrous sodium sulfate 42.8 parts by weight

And uniformly mixed, granulated and dried to make granule wettable powder.

Preparation example 6

(1) Compound of the present invention 5 parts by weight

(2) Polyoxyethylene octylphenyl ether 1 part by weight

(3) Phosphate ester of polyoxyethylene 0.1 parts by weight

(4) Granular calcium carbonate 93.9 parts by weight

Mix (1)~(3) evenly in advance, dilute with an appropriate amount of acetone, spray on (4), remove acetone to make granules.

Preparation Example 7

(1) Compound of the present invention 2.5 parts by weight

(2) N-methyl-2-pyrrolidone 2.5 parts by weight

(3) soybean oil 95.0 parts by weight

Mix and dissolve the above ingredients evenly to make ultra low volume formulation.

Preparation Example 8

(1) Compound of the present invention 40 parts by weight

(2) Oxygenated polyalkylphenyl phosphate-triethanolamine 2 parts by weight

(3) Polysiloxane 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

Mix and pulverize the above ingredients evenly to make water-based suspending agent.

Preparation Example 9

(1) Compound of the present invention 10 parts by weight

(2) Diethylene glycol monoethyl ether 90 parts by weight

Mix the above ingredients evenly to make a solution.

In addition, as the content disclosed in the specification of the present invention, Japanese Patent Application No. 2004-041295 (applied to the Japan Patent Office on February 18, 2004), Japanese Patent Application No. 2004-133722 ( Application to the Japan Patent Office on April 28, 2004), Japanese Patent Application No. 2004-261507 (application to the Japan Patent Office on September 8, 2004), and Japanese Patent Application No. 2004-295778 (application to the Japan Patent Office on October 8, 2004) ) of the manual.

Claims (21)

1. anthranilamides or its salt of a formula (1) expression,

[changing 1]

(in the formula, R ¹For halogen, alkyl, haloalkyl, alkenyl, halogenated alkenyl, alkynyl, halo alkynyl, alkoxyl group, halogenated alkoxy, alkyl-carbonyl, halogenated alkyl carbonyl, alkoxy carbonyl, halo alkoxy carbonyl, can substituted phenyloxycarbonyl, nitro or formyl radical; R ²And R ³Independent respectively is halogen, alkyl, haloalkyl, alkoxyl group, halogenated alkoxy or cyano group; The alkyl of A for being replaced by Y; The C3-4 cycloalkyl that Y replaces for 1 substituting group in the group that can be selected from halogen, alkyl and haloalkyl composition at least; M is 0～4; N is 0 or 1; Q is 0～4, and condition is R ¹Fluorine atom, chlorine atom, bromine atoms or methyl and other R for 2 replacements of phenyl ring ¹During for the halogen of 4 replacements of phenyl ring, this halogen of 4 is fluorine atom or chlorine atom).

2. compound or its salt as claimed in claim 1, wherein R ¹For halogen, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2-6 halogenated alkenyl, C2-6 alkynyl, C2-6 halo alkynyl, C1-6 alkoxyl group, C1-6 halogenated alkoxy, C1-6 alkyl-carbonyl, C1-6 halogenated alkyl carbonyl, C1-6 alkoxy carbonyl, C1-6 halo alkoxy carbonyl, can substituted phenyloxycarbonyl, nitro or formyl radical; R ²And R ³Independent respectively is halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxyl group, C1-6 halogenated alkoxy or cyano group; The C1-6 alkyl of A for being replaced by Y; The C3-4 cycloalkyl that Y replaces for 1 substituting group in the group that can be selected from halogen, C1-6 alkyl and C1-6 haloalkyl composition at least; M is 0～4; N is 0 or 1; Q is 0～4.

3. compound or its salt as claimed in claim 1, wherein R ¹Can substituted phenyloxycarbonyl substituting group be at least 1 that is selected from the group that halogen, alkyl, haloalkyl, alkoxyl group, halogenated alkoxy, alkylthio, halogenated alkylthio, alkyl sulphinyl, haloalkyl sulfinyl, alkyl sulphonyl, halogenated alkyl sulfonyl, cyano group, nitro form.

4. compound or its salt as claimed in claim 1, wherein the C3-4 cycloalkyl of Y does not replace for having.

5. compound or its salt as claimed in claim 1, wherein 1～5 substituting group being selected from the group that halogen, alkyl and haloalkyl form of the C3-4 cycloalkyl of Y replaces.

6. compound or its salt as claimed in claim 1, wherein Y is a cyclopropyl.

7. compound or its salt as claimed in claim 1, wherein R ¹At least 14 replacements, and this R ¹For alkyl, haloalkyl, alkenyl, halogenated alkenyl, alkynyl, halo alkynyl, alkoxyl group, halogenated alkoxy, alkyl-carbonyl, halogenated alkyl carbonyl, alkoxy carbonyl, halo alkoxy carbonyl, can substituted phenyloxycarbonyl, nitro or formyl radical.

8. compound or its salt as claimed in claim 1, wherein R ¹Be halogen, alkyl, haloalkyl, alkyl-carbonyl or formyl radical; R ²Be halogen, haloalkyl or halogenated alkoxy; R ³Be halogen or haloalkyl; The alkyl of A for being replaced by Y; The cyclopropyl that Y replaces for 1 substituting group in the group that can be selected from halogen and alkyl composition at least; M is 1 or 2; N is 0; Q is 1.

9. compound or its salt as claimed in claim 1, wherein R ¹Be halogen, alkyl or haloalkyl; R ²Be halogen, haloalkyl or halogenated alkoxy; R ³Be halogen; The alkyl of A for being replaced by Y; Y is a cyclopropyl; M is 2; N is 0; Q is 1.

10.N-[6-[[(encircle third methyl) amino] carbonyl]-the 2-aminomethyl phenyl]-1-(3-chloro-2-pyridyl)-3-(trifluoromethyl)-1H-pyrazoles-5-methane amide.

11.N-[4-chloro-2-methyl-6-[[Alpha-Methyl-(encircling third methyl) amino] carbonyl]-phenyl]-3-(trifluoromethyl)-1-(3-chloro-2-pyridyl)-1H-pyrazoles-5-methane amide.

12.N-[4-chloro-2-methyl-6-[[Alpha-Methyl-(encircling third methyl) amino] carbonyl]-phenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazoles-5-methane amide.

13.N-[2-bromo-4-chloro-6-[[Alpha-Methyl-(encircling third methyl) amino] carbonyl]-phenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazoles-5-methane amide.

14. the anthranilamides of a formula (I) expression or the manufacture method of its salt, it is characterized in that, (1) make the compound of formula (II) expression and the compound reaction of formula (III) expression, perhaps (2) make the compound of formula (IV) expression and the compound reaction that formula V is represented

[changing 2]

(in the formula, R ¹For halogen, alkyl, haloalkyl, alkenyl, halogenated alkenyl, alkynyl, halo alkynyl, alkoxyl group, halogenated alkoxy, alkyl-carbonyl, halogenated alkyl carbonyl, alkoxy carbonyl, halo alkoxy carbonyl, can substituted phenyloxycarbonyl, nitro or formyl radical; R2 and R3 are independent respectively to be halogen, alkyl, haloalkyl, alkoxyl group, halogenated alkoxy or cyano group; The alkyl of A for being replaced by Y; The C3-4 cycloalkyl that Y replaces for 1 substituting group in the group that can be selected from halogen, alkyl and haloalkyl composition at least; M is 0～4; N is 0 or 1; Q is 0～4, and condition is R ¹Fluorine atom, chlorine atom, bromine atoms or methyl and other R for 2 replacements of phenyl ring ¹During for the halogen of 4 replacements of phenyl ring, this halogen of 4 is fluorine atom or chlorine atom);

[changing 3]

(in the formula, R ¹, A and m as previously mentioned);

[changing 4]

(in the formula, R ², R ³, n and q as previously mentioned, and Z be the chlorine atom ,-OH or C _1-4Alkoxyl group);

[changing 5]

(in the formula, R ¹, R ², R ³, m, n and q as previously mentioned);

Formula V: A-NH ₂(in the formula, A as previously mentioned).

15. a noxious organism control agent, it contains wantonly 1 described anthranilamides of claim 1～13 or its salt as effective constituent.

16. an agriculture and garden noxious organism control agent, it contains wantonly 1 described anthranilamides of claim 1～13 or its salt as effective constituent.

17. a desinsection, kill mite or nematocides, it contains wantonly 1 described anthranilamides of claim 1～13 or its salt as effective constituent.

18. an animal Parasites agent for preventing and eliminating, it contains wantonly 1 described anthranilamides of claim 1～13 or its salt as effective constituent.

19. the agent for preventing and eliminating of an animal ectoparasitism biology, it contains wantonly 1 described anthranilamides of claim 1～13 or its salt as effective constituent.

20. the prevention or the therapeutical agent of the Animal diseases that a zooparasite causes, it contains wantonly 1 described anthranilamides of claim 1～13 or its salt as effective constituent.

21. a method of preventing and kill off harmful organism is used wantonly 1 described anthranilamides or its salt of the claim 1～13 of significant quantity and is prevented and kill off harmful organism.