Red mite control agent

Abstract

The present invention relates to a red mite control agent that contains a compound represented by formula (1) or a salt thereof.

Description

Red mites control agent

[0001] The present invention relates to a chicken mite control agent.

[0002] Various compounds are known as amide derivatives having a pesticidal effect against pests. For example, Patent Document 1 discloses that a composition containing an aromatic carboxylic acid amide derivative as an active ingredient has excellent animal parasite-controlling activity.

[0003] International Publication No. 2011 / 093415

[0004] However, it has not been confirmed that the compound represented by the following formula (1) has a control effect against chicken mites. The problem to be solved by the present invention is to provide a chicken mite control agent that contains a compound represented by the following formula (1) and that maintains a control effect against chicken mites for a long period of time.

[0005] As a result of extensive research, the present inventors have found that a compound represented by the following formula (1) has a long-term control effect against chicken mites, and have thus completed the present invention.

[0006] That is, the present invention includes the following aspects: [1] A compound represented by the following formula (1): (In formula (1), Q 1 represents phenyl or pyridyl optionally substituted with one or more halogen atoms; R 1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms which may be substituted with one or more aliphatic rings; Y 1 and Y 2 each independently represents a halogen atom or a haloalkyl having 1 to 3 carbon atoms.) [2] Q 1 represents phenyl or pyridyl optionally substituted with one fluorine atom, R 1 represents a hydrogen atom or a methyl group optionally substituted with one aliphatic ring; Y 1 and Y 2[3] The control agent according to [1], wherein each independently represents a bromine atom, an iodine atom, or trifluoromethyl. [3] The control agent according to [1], wherein the compound represented by formula (1) is 2-fluoro-3-(N-methylbenzamido)-N-(2-bromo-6-trifluoromethyl-4-(heptafluoropropan-2-yl)phenyl)benzamide, 2-fluoro-3-(4-fluoro-N-methylbenzamido)-N-(2-iodo-6-trifluoromethyl-4-(heptafluoropropan-2-yl)phenyl)benzamide, 2-fluoro-3-(3-fluoro-N-methylbenzamido)-N-(2-iodo-6-trifluoromethyl-4-(heptafluoropropan-2-yl)phenyl)benzamide, 2-fluoro-3-(4-fluorobenzamido)-N-(2-iodo-6-trifluoromethyl The control agent according to [1] or [2], which is selected from the group consisting of 2-fluoro-3-(4-fluoro-N-cyclopropylmethylbenzamide)-N-(2-bromo-6-trifluoromethyl-4-(heptafluoropropan-2-yl)phenyl)benzamide, 2-fluoro-3-(4-fluoro-N-cyclopropylmethylbenzamide)-N-(2-bromo-6-trifluoromethyl-4-(heptafluoropropan-2-yl)phenyl)benzamide, and 2-fluoro-3-(4-fluoro-3-pyridinecarboxyamide)-N-(2-iodo-6-trifluoromethyl-4-(heptafluoropropan-2-yl)phenyl)benzamide. [4] The control agent according to the following formula (1): (In formula (1), Q 1 represents phenyl or pyridyl optionally substituted with one or more halogen atoms; R 1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms which may be substituted with one or more aliphatic rings; Y 1 and Y 2 each independently represents a halogen atom or a haloalkyl having 1 to 3 carbon atoms; 2[5] A composition for controlling chicken mites by applying 50 mg or more of the compound or a salt thereof per 1 m once every 7 days to 1 year. [6] A method for controlling chicken mites, comprising applying the control agent according to any one of [1] to [3] to a habitat of chicken mites or a target organism for chicken mites to infest. 2 [6] The method according to [5], wherein 50 mg or more of the compound or a salt thereof is applied per plant once every 7 days to 1 year.

[0007] According to the present invention, it is possible to provide a chicken mite control agent that contains a compound represented by the following formula (1) and that retains a control effect against chicken mites for a long period of time.

[0008] 1 shows the results of observing the number of red mites present in a red mites trap after spraying Compound (A), a conventional acaricide, or water. 2 shows the results of observing the population density of red mites after spraying Compound (A) or a conventional acaricide.

[0009] Hereinafter, a mode for carrying out the present invention (hereinafter referred to as "the present embodiment") will be described in detail. The present embodiment is an example for explaining the present invention, and is not intended to limit the present invention to the following content. The present invention can be carried out by appropriately modifying it within the scope of its gist.

[0010] As used herein, "alkyl" refers to a hydrocarbon group that is linear, branched, cyclic, or a combination thereof. A cyclic alkyl is a cycloalkyl. Examples of alkyl groups having 1 to 3 carbon atoms include methyl, ethyl, n-propyl, isopropyl, and cyclopropyl.

[0011] In this specification, the term "haloalkyl" refers to an alkyl group substituted with one or more halogen atoms, which may be the same or different. Examples of haloalkyl groups having 1 to 3 carbon atoms include trifluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 3-fluoro-n-propyl, 2,3,3,3-tetrafluoro-n-propyl, heptafluoro-n-propyl, heptafluoro-i-propyl, 1,3-difluoro-2-propyl, 1,1,1-trifluoro-2-propyl, 2,2,3,3,3- Pentafluoro-n-propyl, 1,1,1,3,3,3-hexafluoro-2-propyl, trichloromethyl, 2-chloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, pentachloroethyl, 3-chloro-n-propyl, 2,3,3,3-tetrachloro-n-propyl, heptachloro-n-propyl, heptachloro-i-propyl, 1,3-dichloro-2-propyl, tribromomethyl, 2-bromoethyl, 2,2-dibromoethyl Bromoethyl, 2,2,2-tribromoethyl, pentabromoethyl, 3-bromo-n-propyl, 2,3,3,3-tetrabromo-n-propyl, heptabromo-n-propyl, heptabromo-i-propyl, 1,3-dibromo-2-propyl, triiodomethyl, 2-iodoethyl, 2,2-diiodoethyl, 2,2,2-triiodoethyl, 3-iodo-n-propyl, 2,3,3,3-tetraiodo-n-propyl, 1,3-diiodo-2-propyl -propyl, 1-chloro-3-fluoro-2-propyl, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propyl, 1,1,1,3,3,3-hexafluoro-2-bromo-2-propyl, 1,1,2,3,3,3-hexafluoro-2-chloro-n-propyl, 1,1,2,3,3,3-hexafluoro-2-bromo-n-propyl, and 1,1,2,3,3,3-hexafluoro-1-bromo-2-propyl.

[0012] In this specification, the term "halogen atom" refers to, for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.

[0013] As used herein, an "aliphatic ring" refers to a 3- to 10-membered monocyclic or bicyclic ring containing carbon atoms as ring constituent atoms. As used herein, the "aliphatic ring" referred to as "optionally substituted with an aliphatic ring" includes, for example, cycloalkyl. Examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, and 4-methylcyclohexyl. The aliphatic ring may be a cycloalkyl having 3 to 10, 3 to 8, or 3 to 7 carbon atoms.

[0014] As used herein, the term "optionally substituted" means substituted with a substituent or unsubstituted. Therefore, "optionally substituted" has the same meaning as "substituted or unsubstituted."

[0015] In this specification, "mites" refers to organisms with the scientific name Dermanyssus gallinae, which belong to the family Mitellidae in the order Acari.

[0016] <Compound Represented by Formula (1)> One embodiment of the present invention is a chicken mite control agent comprising a compound represented by the following formula (1) (hereinafter also referred to as "compound (1)") or a salt thereof: In formula (1), Q 1 represents phenyl or pyridyl optionally substituted with one or more halogen atoms, R 1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms which may be substituted with one or more aliphatic rings; Y 1 and Y 2 each independently represents a halogen atom or haloalkyl having 1 to 3 carbon atoms.

[0017] In formula (1), Q 1 preferably represents phenyl or pyridyl optionally substituted with 1 to 3 halogen atoms, more preferably represents phenyl or pyridyl optionally substituted with one halogen atom, and even more preferably represents phenyl or pyridyl optionally substituted with one fluorine atom.

[0018] Q 1 preferably represents any of the following structures: In the following structures, the dashed line represents a bond to the carbonyl.

[0019] In formula (1), R 1 preferably represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms which may be substituted with one aliphatic ring, more preferably represents a hydrogen atom or a methyl group which may be substituted with one aliphatic ring, and even more preferably represents a hydrogen atom or a methyl group which may be substituted with one cyclopropyl group. Methyl substituted with one cyclopropyl group is also called cyclopropylmethyl. R 1 preferably represents a hydrogen atom, methyl, ethyl or cyclopropylmethyl, more preferably represents a hydrogen atom, methyl or cyclopropylmethyl.

[0020] In formula (1), Y 1 and Y 2 preferably each independently represents a fluorine atom, a bromine atom, an iodine atom, or a haloalkyl having 1 to 3 carbon atoms, more preferably a bromine atom, an iodine atom, or an alkyl having 1 to 3 carbon atoms substituted with one or more fluorine atoms, and even more preferably a methyl substituted with a bromine atom, an iodine atom, or one or more fluorine atoms. 1 and Y 2 Preferably, either one of Y is a halogen atom. 1 and Y 2 The combination of Y preferably represents a bromine atom or an iodine atom and trifluoromethyl. 1 and Y 2 may be the same, in which case they preferably represent a bromine atom or an iodine atom, and more preferably represent a bromine atom.

[0021] In the present embodiment, the compound (1) is not particularly limited, but examples thereof include 2-fluoro-3-(N-methylbenzamido)-N-(2-bromo-6-trifluoromethyl-4-(heptafluoropropan-2-yl)phenyl)benzamide, 2-fluoro-3-(4-fluoro-N-methylbenzamido)-N-(2-iodo-6-trifluoromethyl-4-(heptafluoropropan-2-yl)phenyl)benzamide, 2-fluoro-3-(3-fluoro-N-methylbenzamido)-N-(2-iodo-6-trifluoromethyl-4-(heptafluoropropan-2-yl)phenyl)benzamide, 2-fluoro-3-(4-fluorobenzamido)-N- (2-iodo-6-trifluoromethyl-4-(heptafluoropropan-2-yl)phenyl)benzamide, 2-fluoro-3-(N-methylbenzamide)-N-(2,6-dibromo-4-(heptafluoropropan-2-yl)phenyl)benzamide, 2-fluoro-3-(4-fluoro-N-cyclopropylmethylbenzamide)-N-(2-bromo-6-trifluoromethyl-4-(heptafluoropropan-2-yl)phenyl)benzamide, and 2-fluoro-3-(4-fluoro-3-pyridinecarboxamide)-N-(2-iodo-6-trifluoromethyl-4-(heptafluoropropan-2-yl)phenyl)benzamide.

[0022] Compound (1) may contain an asymmetric atom. In this case, the ratio of isomers may be a single isomer or a mixture ratio of any proportion, and is not particularly limited.

[0023] Compound (1) may be a geometric isomer. In this case, the isomer ratio may be a single isomer or a mixture ratio of any isomer, and is not particularly limited.

[0024] Compound (1) may form a salt, such as a salt with an acid such as hydrochloric acid, sulfuric acid, acetic acid, fumaric acid, or maleic acid, or a metal salt such as a sodium salt, potassium salt, or calcium salt, but is not particularly limited as long as it can be used as a chicken mite control agent.

[0025] <Method for producing compound (1)> Compound (1) can be produced according to the methods described in, for example, WO 2011 / 093415, WO 2020 / 001067, JP 2020-534334 A, Chinese Patent Application Publication No. 112707836, Chinese Patent Application Publication No. 112707841, and Chinese Patent Application Publication No. 116178198, or methods similar thereto or a combination thereof.

[0026] <Red mites control agent> The red mites control agent of this embodiment is not bound by theory regarding the control of red mites, but the action of the red mites control agent of this embodiment is presumed to be as follows. As shown in the examples, the red mites control agent of this embodiment can eliminate red mites by causing them to die through a lethal effect. That is, the red mites control agent of this embodiment may be a red mite extermination agent, a red miticide, an application agent for controlling red mites, or a composition for controlling red mites. Furthermore, by applying the red mites control agent of this embodiment to habitats of red mites or organisms that are parasitized by red mites, it is possible to prevent the occurrence of red mites, the proliferation of red mites, and / or the parasitization of red mites by red mites on organisms that are parasitized by red mites. For example, when eliminating chicken mites that parasitize poultry, the chicken mites can be eliminated by using the chicken mite control agent of this embodiment without directly treating the target organisms of the chicken mites. Furthermore, chicken mites include both adult mites and newly hatched mites, and the chicken mite control agent of this embodiment can control all chicken mites regardless of their developmental stage. While not particularly limited, chicken mites can be controlled, for example, by direct contact of chicken mites with compound (1) or by contact of other chicken mites with chicken mites that have come into contact with compound (1). Furthermore, the chicken mite control agent of this embodiment has superior immediate and residual effects compared to conventional chicken mite control agents. As a result, a single use of the chicken mite control agent of this embodiment can provide long-term control of chicken mites that have appeared before use and newly invaded chicken mites (including newly hatched chicken mites) after use. Furthermore, the inventors believe that the reason why the chicken mite control agent of this embodiment has excellent residual activity is as follows, although this is not intended to be a limitation: because compound (1) has excellent long-term residual activity, it is thought that a single use of the chicken mite control agent of this embodiment will result in a long-lasting effect of controlling chicken mites.

[0027] The chicken mite control agent of this embodiment contains compound (1) as an active ingredient and may contain one or more types of compound (1), and preferably contains one type of compound (1).

[0028] The chicken mite control agent of this embodiment may contain any component other than compound (1) to the extent that the effect is not impaired. Examples of the optional component other than compound (1) include antifreeze agents, thickeners, surfactants, preservatives / antifungals, antifoaming agents, colorants, solvents / oils, humectants, sugars, water-soluble polymers, inorganic salts, UV screening agents, UV absorbers, antioxidants, latexes / emulsions, fragrances, mineral powders, pH adjusters, liquid carriers, solid carriers, gaseous carriers, etc.

[0029] The antifreeze agent is not particularly limited, but examples thereof include ethylene glycol, diethylene glycol, propylene glycol, and glycerin.

[0030] Examples of thickening agents include, but are not limited to, natural gums such as xanthan gum, welan gum, guar gum, tragacanth gum, and gum arabic; inorganic mineral powders such as bentonite, smectite, talc, white carbon (precipitated silica), clay, sepiolite, attapulgite, laponite, montmorillonite, and hectorite; cellulose derivatives or salts thereof such as carboxymethyl cellulose, hydroxyethyl cellulose, carboxyethyl cellulose, methyl cellulose, hydroxypropyl cellulose, and hydroxyethyl cellulose; starch derivatives such as various grades of dextrin and sodium carboxymethyl starch; natural products or derivatives thereof such as sodium alginate and sodium caseinate; and water-soluble synthetic polymers such as polyvinyl alcohol, polyacrylic acid and its derivatives, and polyvinylpyrrolidone. Some of the thickening agents exemplified above may also be used as water-soluble polymers. Some of the thickening agents exemplified above may also be used as mineral powders.

[0031] The surfactant is not particularly limited, but examples thereof include anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, etc. The surfactants exemplified above can also be used as wetting agents.

[0032] The anionic surfactant is not particularly limited, but examples thereof include lignin sulfonates, aryl sulfonates (alkylbenzene sulfonates such as sodium dodecylbenzene sulfonate; alkylnaphthalene sulfonates such as sodium alkylnaphthalene sulfonate, sodium monoalkylnaphthalene sulfonate, and sodium dialkylnaphthalene sulfonate; etc.), formalin condensates of aryl sulfonates (naphthalene sulfonate-formalin condensate salts such as naphthalene sulfonate-formalin condensate sodium salt; alkylnaphthalene sulfonate-formalin condensate salts such as alkylnaphthalene sulfonate-formalin condensate sodium salt; phenolsulfonate-formalin condensate salts such as phenolsulfonate-formalin condensate sodium salt; α-olefin sulfonates (sodium α-olefin sulfonate, etc.), alkyl sulfonates (sodium alkyl sulfonate, etc.), alkyl diphenyl ether disulfonates (sodium alkyl diphenyl ether disulfonate, etc.), polyoxyethylene alkyl alkylphenyl ether sulfonates (such as sodium polyoxyethylene alkylphenyl ether sulfonate), polyoxyethylene alkyl ether sulfosuccinate half esters, alkyl sulfates (such as sodium lauryl sulfate), sulfosuccinates (such as dialkyl sulfosuccinates), polyoxyalkylene aryl ether sulfates (such as polyoxyethylene alkyl aryl ether sulfates, polyoxyethylene styryl phenyl ether sulfates, polyoxyethylene benzyl phenyl ether sulfates, polyoxyalkylene styryl phenyl ether sulfates), polyoxyalkylene alkyl ether sulfates (polyoxyethylene alkyl ether sulfates such as polyoxyethylene lauryl ether sulfate; etc.), polyoxyethylene polyoxypropylene block polymer sulfates (such as sodium polyoxyethylene polyoxypropylene block polymer sulfate), polyoxyalkylene alkyl ether acetates (polyoxyethylene alkyl ether acetates such as sodium polyoxyethylene lauryl ether acetate;etc.), polyoxyalkylene aryl ether phosphates (polyoxyethylene styrenated phenyl ether phosphate, polyoxyethylene styryl phenyl ether phosphate, polyoxyethylene benzyl phenyl ether phosphate, polyoxyethylene alkyl phenylene block polymer phosphate (polyoxyethylene polyoxypropylene block polymer phosphate etc.), polyoxyalkylene alkyl ether phosphates (polyoxyethylene lauryl ether phosphate monoethanolamine salt, polyoxyethylene lauryl ether phosphate ester etc.), polyoxyethylene polyoxypropylene sodium phosphate etc.), alkyl phosphate esters (alkyl phosphoric acid, sodium alkyl phosphate etc.), methyl taurate salts (sodium oleyl methyl tauride etc.), polycarboxylates (sodium alkylene maleate copolymer, maleic acid isobutylene copolymer, acrylic acid maleic acid copolymer sodium, polycarboxylate sodium distyryl phenyl ether sulfate ammonium salt etc.), fatty acid salts (semi-hardened beef tallow fatty acid soda soap etc.);

[0033] The cationic surfactant is not particularly limited, but examples thereof include monoalkylamine salts, dialkylamine salts, trialkylamine salts, alkyltrimethylammonium salts, dialkyldimethylammonium salts, alkyldimethylbenzylammonium salts, and alkyldimethylaminopropylamides.

[0034] The nonionic surfactant is not particularly limited, but examples thereof include aliphatic alcohol alkylene oxide adducts, polyalkyleneoxy fatty acid esters, and alkyl ether surfactants.

[0035] The amphoteric surfactant is not particularly limited, but examples thereof include alkyl betaine, fatty acid amidopropyl betaine, 2-alkyl-N-carboxylmethyl-N-hydroxyethyl-imidazolinium betaine, alkyl diethylene triamino acetic acid, dialkyl diethylene triamino acetic acid, and alkyl amine oxide.

[0036] The antiseptic / antifungal agent is not particularly limited, but examples thereof include benzothiazole derivatives (for example, 1,2-benzisothiazolin-3-one), sorbic acid, potassium sorbate, and butyl p-oxybenzoate.

[0037] The antifoaming agent is not particularly limited, but examples thereof include silicone-based, acetylene glycol-based, fluorine-based, and fatty acid-based antifoaming agents.

[0038] The colorant is not particularly limited, but examples thereof include food dyes, zinc oxide, cuprous oxide, lead monoxide, watching red, chlorine process titanium oxide pigment, oil furnace black, yellow lead, yellow iron oxide, oxysulfide phosphor, cadmium yellow, cadmium red, ultramarine, fluorescent pigment, graphite, black iron oxide, ultrafine calcium carbonate, cobalt blue, cobalt green, cobalt purple, chalk, Prussian blue, thermal black, chromium oxide, titanium oxide (athanace), titanium oxide (rutile), terbium oxide, copper oxide, disazo yellow, red iron oxide, granulated carbon black, brown iron oxide, channel black, ultrafine particle titanium oxide, iron black, natural graphite powder, natural earthy graphite, copper phthalocyanine blue, copper phthalocyanine green, permanent red, vanadate phosphor, fine particle titanium oxide, Fast Yellow 10G, red iron oxide, and molybdenum red.

[0039] The solvents and oils are not particularly limited, but examples thereof include aromatic hydrocarbons such as 1,2-dimethyl-4-ethylbenzene, methylnaphthalene, 1-phenyl-1-xylylethane, and 1-xylyl-1,3-diphenylbutane; paraffinic hydrocarbons such as normal paraffin, isoparaffin, and liquid paraffin; polybasic acid alcohol esters such as diisobutyl adipate, diisodecyl adipate, didecyl phthalate, diethylhexyl phthalate, 2-ethylhexyl trimellitate, and tridecyl trimellitate; fatty acid alcohol esters such as 2-ethylhexanoate, cocoate cetyl, methyl laurate, and methyl oleate; polyhydric alcohol fatty acid esters such as sorbitan monolaurate and sorbitan monooleate; and higher alcohols such as octyl alcohol and lauryl alcohol.

[0040] The sugars are not particularly limited, but examples thereof include α-hydrated lactose, α-anhydrous lactose, β-anhydrous lactose, diol compounds, glycerin and its derivatives, pentaerythritol, sorbitol, xylitol, sucrose, glucose, and fructose.

[0041] The inorganic salts are not particularly limited, but examples thereof include calcium silicate, magnesium carbonate, calcium carbonate, sodium carbonate, sodium hydrogen carbonate, ammonium sulfate, sodium sulfate, magnesium sulfate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate, and potassium chloride.

[0042] The ultraviolet screening agent is not particularly limited, but examples thereof include salicylic acid-based ultraviolet screening agents and benzophenone-based ultraviolet screening agents.

[0043] The ultraviolet absorber is not particularly limited, but examples thereof include inorganic compound-based ultraviolet absorbers such as titanium dioxide; and organic compound-based ultraviolet absorbers such as benzotriazole, benzophenone, triazine, benzoate, and salicylate.

[0044] The antioxidant is not particularly limited, but examples thereof include hindered phenol-based antioxidants, sulfur-based antioxidants, phosphorus-based antioxidants, amine-based antioxidants, lactone-based antioxidants, and vitamin E-based antioxidants.

[0045] The latexes and emulsions are not particularly limited, but examples thereof include latexes and emulsions such as styrene-butadiene copolymer, styrene-acrylic copolymer, methyl methacrylate-butadiene copolymer, ethylene-vinyl acetate copolymer, ethylene-acrylic copolymer, silicone-acrylic copolymer, polyurethane, and polyurea.

[0046] The fragrances are not particularly limited, but examples thereof include lavender oil, jasmine oil, rose oil, lemon oil, orange oil, peppermint oil, thyme oil, calamus oil, fennel oil, cedar oil, hiba oil, cypress oil, eucalyptus oil, camphor, peppermint oil, spearmint oil, geraniol, citronellal, eugenol, limonene, mandarin oil, spruce, and citronellol.

[0047] The pH adjuster is not particularly limited, and examples thereof include inorganic acids such as hydrochloric acid and phosphoric acid; organic acids such as citric acid, phthalic acid, and succinic acid; organic metal salts such as sodium citrate and potassium hydrogen phthalate; inorganic metal salts such as disodium hydrogen phosphate, sodium dihydrogen phosphate, dipotassium hydrogen phosphate, potassium dihydrogen phosphate, sodium carbonate, potassium carbonate, and sodium borate; hydroxides such as sodium hydroxide and potassium hydroxide; and organic amines such as triethanolamine. The pH may also be adjusted using a buffer solution of phosphoric acid, acetic acid, or citric acid containing a component described as a pH adjuster.

[0048] The chicken mite control agent of this embodiment may contain a carrier, and examples of the carrier include a liquid carrier, a solid carrier, a gaseous carrier, etc. As a solid carrier, for example, a mineral powder may be used, and as a liquid carrier, for example, water may be used.

[0049] The chicken mite control agent of this embodiment may be used in combination with other insecticidal components, as long as its effectiveness is not impaired. Examples of methods for using the compound (1) in combination with other insecticidal components include formulating compound (1) and the other insecticidal components into a single formulation, mixing the components formulated in separate formulations before use, simultaneously using the components formulated in separate formulations, and using one of the components formulated in separate formulations after using the other.

[0050] Examples of dosage forms of the chicken mite control agent include dusts, granules, powders, wettable powders, water-soluble powders, emulsions, liquids, oils, aerosols, pastes, fumigants, fumigants, liniments, microcapsules, and packs, with wettable powders being preferred. Examples of wettable powders include FL (flowable) agents, SC (suspension concentrate) agents, DF (dry flowable) agents, water-dispersible granules, SE (suspo emulsion) agents, and water-soluble packaged formulations, with FL (flowable) agents being preferred.

[0051] <Method for producing chicken mite control agent> The method for producing the chicken mite control agent is not particularly limited as long as it is a method that can produce a composition containing compound (1), and known production methods can be used depending on the dosage form. Examples of the method for producing the chicken mite control agent include a method of mixing compound (1) with any component other than compound (1).

[0052] <Method for controlling chicken mites> One embodiment of the present invention is a method for controlling chicken mites, which comprises applying a chicken mites control agent to a habitat of chicken mites or a target organism parasitized by chicken mites.

[0053] Examples of target organisms that can be parasitized by chicken mites include poultry. Examples of poultry include chickens, ducks, geese, and turkeys, with chickens being preferred.

[0054] Examples of habitats for mites or organisms that are parasitized by mites include breeding facilities for the organisms that are parasitized by mites. When the organisms that are parasitized by mites are chickens, examples of habitats for mites or organisms that are parasitized by mites include chicken coops, and include, but are not limited to, the floors, walls, ceilings, egg pans, feeding troughs, and cages for raising chickens.

[0055] The chicken mite control agent of this embodiment may be applied either indoors or outdoors, but from the viewpoint of obtaining a long-term chicken mite control effect, it is preferably applied indoors.

[0056] The method of applying the chicken mite control agent is not particularly limited as long as it brings chicken mites into contact with the agent, and for example, known application methods can be used depending on the formulation. Application methods include, for example, coating, spraying, and atomizing, with spraying and atomizing being preferred.

[0057] The application amount of the chicken mite control agent is not particularly limited, but for example, 2 It is preferable to apply 50 mg or more of the compound (1) per m 2 It is more preferable to apply 70 mg or more of compound (1) per m 2 It is even more preferable to apply 90 mg or more of compound (1) per 1000 mg of the agent. The application amount is not particularly limited as long as the desired application amount can be achieved, but the agent may be applied directly to the target, or the agent may be diluted with water prior to application. Examples of water used for dilution include tap water, ion-exchanged water, distilled water, filtered water, sterilized water, and natural water such as groundwater. One or more types of water may be used in combination. When the agent is diluted with water and applied, the content of compound (1) in the water-diluted formulation is preferably 0.00625 to 0.10000% by mass, more preferably 0.00700 to 0.07500% by mass, and even more preferably 0.00775 to 0.05000% by mass, based on 100% by mass of the water-diluted formulation.

[0058] An example of a method for applying a chicken mite control agent will be described. When 5% by mass of compound (1) is contained relative to 100% by mass of the chicken mite control agent, the chicken mite control agent may be used after being diluted 200 times with water. In this case, the content of compound (1) in the formulation diluted with water is 0.025% by mass relative to 100% by mass of the formulation diluted 200 times with water. Furthermore, the formulation diluted 200 times with 400 mL of water is added to 1 ml 2 When treated with 1 m3, the application amount of the red mites control agent is 2 In addition, the method for applying the chicken mite control agent may be the method described on the product package.

[0059] The frequency of application of the chicken mite control agent is not particularly limited, but for example, it is preferably applied once every 7 days to 1 year, more preferably once every 50 days to 1 year, and even more preferably once every 80 days to 1 year. The chicken mite control agent of this embodiment has excellent residual activity, and therefore can be highly effective in controlling chicken mites by applying it once every 7 days to 1 year. Furthermore, there are no particular limitations on the time of application of the chicken mite control agent, and it can be applied whenever necessary throughout the year.

[0060] The method of applying the chicken mite control agent is not particularly limited, but for example, 2 It is preferable to apply 50 mg or more of the compound (1) per 1 m once every 7 days to 1 year. 2 It is more preferable to apply 70 mg or more of compound (1) per m once every 7 days to 1 year. 2 It is more preferable to apply 90 mg or more of compound (1) per 1 m once every 7 days to 1 year. 2 It is more preferable to apply 50 mg or more of compound (1) per m once every 50 days to 1 year. 2 It is more preferable to apply 50 mg or more of compound (1) per 1000g of the plant once every 80 days to 1 year.

[0061] The method for applying the chicken mite control agent is to apply the compound (1) at a treatment amount of 100 mg / m 2 One spraying treatment was carried out so that the2 It is preferable that the amount of compound (1) present per 1 m is 0.1 mg or more. 2 When the amount of compound (1) present per unit area is 0.1 mg or more, an excellent effect of controlling chicken mites can be obtained. 2 The amount of compound (1) present per unit area can be determined, for example, by attaching an adhesive tape to the sprayed area and analyzing the amount of compound (1) adhering to the adhesive tape, or by wiping the sprayed area with a clean cloth, nonwoven fabric, or the like and analyzing the amount of compound (1) adhering to the cloth, nonwoven fabric, or the like.

[0062] <Mite control composition> The composition for controlling mites of this embodiment (also referred to as "mite control composition" in this specification) contains compound (1). The contents of the explanation about the mite control agent etc. of this embodiment also apply to the mite control composition of this embodiment. Furthermore, in the contents of the explanation about the mite control agent etc. of this embodiment, the term "mite control agent" can be read as "mite control composition". The mite control composition contains 1 ml 2 The composition may be a composition for controlling chicken mites, which is applied in an amount of 50 mg or more per plant once every 7 days to 1 year.

[0063] The content of compound (1) in the chicken mite control composition of this embodiment is not particularly limited, as long as it is an amount that allows formulation. For example, it is preferably 0.1 to 50% by mass, more preferably 1 to 40% by mass, and even more preferably 3 to 30% by mass, relative to 100% by mass of the chicken mite control composition. The content in the chicken mite control composition may be determined from the charging ratio during production of the chicken mite control composition, or may be the content listed on the product package.

[0064] The present embodiment will be described in more detail below based on examples, but the present embodiment is not limited to these examples.

[0065] <Synthesis of Compound (1)> [Synthesis Example 1] Synthesis of 2-fluoro-3-(N-methylbenzamido)-N-(2-bromo-6-trifluoromethyl-4-(heptafluoropropan-2-yl)phenyl)benzamide According to the method described in WO 2011 / 093415, 2-fluoro-3-(N-methylbenzamido)-N-(2-bromo-6-trifluoromethyl-4-(heptafluoropropan-2-yl)phenyl)benzamide (hereinafter also referred to as "compound (A)") was synthesized.

[0066] <Production Example of a Chicken Mite Control Agent Containing Compound (A)> 5.10% by mass of compound (A) (purity >98%), 8.05% by mass of antifreeze (propylene glycol), 0.60% by mass of thickener (Kunipia F (bentonite, manufactured by Kunimine Industries Co., Ltd.), 0.28% by mass of Keltrol CG (xanthan gum, manufactured by Sansho Co., Ltd.)), 0.25% by mass of wetting agent (dioctyl sodium sulfosuccinate), 0.20% by mass of preservative (1,2-benzisothiazolin-3-one), 0.01% by mass of antifoaming agent (silicone, KM-72, manufactured by Shin-Etsu Chemical Co., Ltd.), and 85.51% by mass of purified water were mixed to produce a chicken mite control agent containing compound (A) as a flowable agent (hereinafter also referred to as "chick mite control agent (A)"). The compound (A) was contained in an amount of 5% by mass relative to 100% by mass of the chicken mite control agent.

[0067] <Red mites control test 1> Compound (A) and spinosad, a conventional acaricide, were prepared using acetone to the concentrations shown in the table below. The prepared solution was placed in a pipette, the acetone evaporated, and a dry film was created inside the pipette. Approximately 20 adult red mites were then collected by suction into the pipette, and the red mites mortality rate was observed after 24, 48, and 72 hours of exposure. The results are shown in the table below. When the treatment concentration of compound (A) was 0.13 mg a.i. (active ingredient) / m 2 The mortality rate of chicken mites was 95%. Compound (A) was found to be effective in controlling chicken mites and to have an excellent immediate effect.

[0068] <Red mites control test 2> The red mites control agent (A) was diluted with water to a concentration of 0.025% by mass of the compound (A) to obtain a diluted solution. 2 The compound (A) was sprayed onto a cage for raising chickens so that the amount of compound (A) sprayed was 1 m. 2 In addition, the conventional acaricides etoxazole and spinosad were sprayed at a dose of 1 m 2 The solution was sprayed onto chicken cages so that the doses were 100 mg and 1600 mg per cage. As a control, water was sprayed onto the chicken cages. Then, chicken mite traps were placed in the chicken rearing room, and the number of chicken mites present in the traps was observed. The results are shown in Figure 1. The number of chicken mites was scored based on the following score, and the change in the average score was evaluated.

[0069] Score 0: Not a single live red mites can be found in the trap. 1: 1 to 100 live mites can be found in the trap. 2: 101 to 1000 live mites can be found in the trap. 3: 1001 to 5000 live mites can be found in the trap. 4: 5001 to 10000 live mites can be found in the trap. 5: 10001 or more live mites can be found in the trap.

[0070] It was found that compound (A) had an excellent effect in controlling chicken mites compared to the control group and conventional acaricides. Furthermore, since there was no increase in the number of chicken mites even 70 days after the start of the test, it was found that compound (A) had excellent residual efficacy.

[0071] <Red mites control test 3> The red mites control agent (A) was diluted with water to a concentration of 0.025% by mass of compound (A) to obtain a diluted solution. The diluted solution was applied at 400 mL / m 2 The compound (A) was sprayed onto a cage for raising chickens so that the amount of compound (A) sprayed was 1 m. 2 Spinosad was used as a conventional acaricide at a spray volume of 1 m 2The solution was sprayed onto chicken cages so that the concentration was 1600 mg per cage. Then, chicken red mite traps were set up in the chicken coop, and the population density of the mites present in the traps was observed. The results are shown in Figure 2. The day before spraying was defined as day 1. The population density of the mites was evaluated based on the following scores:

[0072] Score 0: Not a single live red mites were found in the trap. 1: No colonies were formed, and live mites were scattered. Even if there were a small cluster of mites, it was determined that the cluster was no larger than 1 cm. 2 2: Less than 1 cm is not considered a colony. 2 More than 5cm 2 3: Forming colonies of less than 5 cm 2 Above, 10cm 2 4: Forming colonies of less than 10 cm 2 More than one colony has been formed.

[0073] It was found that compound (A) had excellent immediate effectiveness compared to conventional acaricides in chicken coops. Furthermore, since there was no increase in the number of red mites even 84 days after the start of the test, it was also found that compound (A) had excellent residual effectiveness.

Claims

1. The following formula (1): (In formula (1), Q 1 represents phenyl or pyridyl optionally substituted with one or more halogen atoms; R 1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms which may be substituted with one or more aliphatic rings; Y 1 and Y 2 and each independently represent a halogen atom or a haloalkyl having 1 to 3 carbon atoms, or a salt thereof.

2. Q 1 represents phenyl or pyridyl optionally substituted with one fluorine atom, R 1 represents a hydrogen atom or a methyl group optionally substituted with one aliphatic ring; Y 1 and Y 2 The control agent according to claim 1, wherein each independently represents a bromine atom, an iodine atom, or trifluoromethyl.

3. The compound represented by formula (1) is 2-fluoro-3-(N-methylbenzamido)-N-(2-bromo-6-trifluoromethyl-4-(heptafluoropropan-2-yl)phenyl)benzamide, 2-fluoro-3-(4-fluoro-N-methylbenzamido)-N-(2-iodo-6-trifluoromethyl-4-(heptafluoropropan-2-yl)phenyl)benzamide, 2-fluoro-3-(3-fluoro-N-methylbenzamido)-N-(2-iodo-6-trifluoromethyl-4-(heptafluoropropan-2-yl)phenyl)benzamide, 2-fluoro-3-(4-fluorobenzamido)-N-(2-iodo-6-trifluoromethyl-4-(heptafluoropropan-2-yl)phenyl)benzamide, 2-fluoro-3-(4-fluoro-N-cyclopropylmethylbenzamide) -N- (2-bromo-6-trifluoromethyl-4- (heptafluoropropan-2-yl) phenyl) benzamide, 2-fluoro-3-(4-fluoro-N-cyclopropylmethylbenzamide) -N- (2-bromo-6-trifluoromethyl-4- (heptafluoropropan-2-yl) phenyl) benzamide, or 2-fluoro-3-(4-fluoro-3-pyridinecarboxamide) -N- (2-iodo-6-trifluoromethyl-4- (heptafluoropropan-2-yl) phenyl) benzamide, the control agent according to claim 1.

4. The following formula (1): (In formula (1), Q 1 represents phenyl or pyridyl optionally substituted with one or more halogen atoms; R 1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms which may be substituted with one or more aliphatic rings; Y 1 and Y 2 each independently represents a halogen atom or a haloalkyl having 1 to 3 carbon atoms; 2 A composition for controlling chicken mites, which comprises applying 50 mg or more of the compound or a salt thereof per plant once every 7 days to 1 year.

5. A method for controlling chicken mites, comprising applying the control agent according to any one of claims 1 to 3 to a habitat of chicken mites or an organism that is parasitized by chicken mites.

6. 1m 2 6. The method according to claim 5, wherein 50 mg or more of the compound or a salt thereof is applied per plant once every 7 days to 1 year.

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