KR102582639B1 - Novel pyrimidine sulfonamide derivatives and a mite controlling composition comprising thereof - Google Patents

Abstract

The present invention relates to a novel amide derivative and a composition for controlling ticks containing the same. By introducing a heterocyclic substituent to the amide derivative, a composition for controlling ticks is provided which has an excellent tick control effect compared to an amide derivative with a single ring substituted. can be provided.

Description

Novel amide derivatives and a mite controlling composition comprising the same {Novel pyrimidine sulfonamide derivatives and a mite controlling composition comprising the same}

The present invention relates to a novel amide derivative and a composition for controlling ticks containing the same.

Various pesticides have been used for the purpose of biological control, but the pesticides used conventionally do not have sufficient insecticidal effect, the insecticidal effect is not consistent after application, or the insecticidal effect does not last long because it evaporates in a short period of time after application to the target organism. Therefore, there were problems such as repeated use of pesticides, resulting in resistance to pesticides, and also harmful to the organisms targeted for control, as it disrupts the nervous system through chemical action.

In the case of livestock, including poultry, blood sucking by pests such as ticks often causes itching, anemia, or even death. It can also cause skin diseases in mammals, including humans, such as poultry farmers. Accordingly, there is a need for the development of a pest control agent that has excellent insecticidal power and is non-toxic, so it can replace existing organic synthetic chemicals, has excellent pest control effects, and is sustainable for a long period of time.

Chicken mites (poultry red mite, Dermanyssus gallinae) belong to the order Arachnoid mites and are external parasites that live on poultry and feed on blood. They are distributed worldwide and are vectors for diseases such as fowl typhus, colibacillosis, and fowl pox. It is the causative agent of mixed infections.

Chicken mites suck blood for an extremely short period of time, about 30 minutes to 1 hour and 30 minutes at night, and hide in the feed, crevices of the chicken house, egg transport belts, cages, etc. for the rest of the time, making them very difficult to control. It is a very difficult pest to control because it can survive for months. In particular, when chicken mites suck blood from laying hens, the damage is widely known as it reduces egg production and egg quality, causes anemia, and causes death. Chicken mites suck blood from not only poultry but also mammals, including humans, causing itching and dermatitis in workers. In Japan, they have become a hygienic problem by causing eczema and allergic reactions in workers.

Although it is effective in removing chicken mites, animal pesticides made of pyrethroid, organo phosphorus, and carbamate ingredients, which belong to pesticides, have been used to date. However, if used continuously, it causes extreme irritation in chickens, reduces weight gain and egg laying rate, increases the resistance of mites, and causes environmental pollution and residual problems in eggs.

Therefore, interest in pesticides that do not cause problems caused by chemical treatment is increasing more than ever, and in particular, in order to find an appropriate control method suitable for the ecology of poultry such as chickens, There is a need for the development of tick control agents that can replace chemical control agents.

Meanwhile, as prior literature related to amide derivatives and their compositions for controlling ticks, Korean Patent Publication No. 10-2010-0112570 discloses an aminobenzamide derivative as a useful animal parasite control agent, and Korean Patent No. 10-1409077 discloses an amide derivative, A pest control agent containing the amide derivative and a method of using the same were disclosed, and a method for producing the amide derivative was disclosed in Korean Patent No. 10-1259709. However, there is no previous report disclosing the compound in which a heterocyclic ring is substituted in an amide compound as in the present invention and the anti-mite effect due to the introduction of the substituent.

Accordingly, in the process of studying amide derivatives, the present inventors completed the present invention by confirming that amide derivatives with a heterocyclic ring substituted at a specific position have significantly improved tick control effects compared to amide derivatives with a single ring substituted.

Korean Patent Publication No. 10-2010-0112570, Aminobenzamide derivatives as useful animal parasite control agents, published on October 19, 2010. Korean Patent No. 10-1409077, Amide derivatives, harmful organism control agents containing amide derivatives and methods of use thereof, registered on June 11, 2014. Korean Patent No. 10-1259709, Manufacturing method of amide derivatives, registered on April 24, 2013.

Seungju Lee et al., Susceptibility evaluation of chicken mites in 5 regions using 11 types of acaricides, Korean J. Appl. Entomol., 56(4), 427-434, 2017. Lim Cheon-ik et al., Effect of spraying cypress essential oil on laying hens on chicken mites, Korean J. Poult. Sci., 45(3), 193-200, 2018.

The purpose of the present invention is to provide a novel amide derivative and a composition containing the same for controlling ticks, particularly a composition for controlling chicken ticks.

The present invention relates to a compound represented by the following formula (1) or a pharmaceutically acceptable salt thereof.

[Formula 1]

In Formula 1,

R ₁ is substituted or unsubstituted C ₄ -C ₁₀ heterocycloalkyl, substituted or unsubstituted C ₄ -C ₁₀ heteroaryl, substituted or unsubstituted C ₄ -C ₁₀ heterocycloalkyl and substituted or unsubstituted C ₄ -C ₁₀ heteroaryl is substituted with a substituent selected from the group consisting of fused heterocycles,

At this time, the substituted heterocycloalkyl and substituted heteroaryl are hydrogen, hydroxy, halogen, C ₁ -C ₆ haloalkyl, cyano, amino, nitro, S-(C ₁ -C ₆ alkyl), C ₁ - is substituted with one or more substituents selected from the group consisting of C ₆ alkyl and C ₁ -C ₆ alkoxy;

R ₂ is substituted with hydrogen or a C ₁ -C ₆ alkyl substituent;

R ₃ is substituted with a hydrogen or halogen substituent;

R ₄ is hydrogen, hydroxy, halogen, C ₁ -C ₆ haloalkyl, cyano, amino, nitro, S-(C ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl and C ₁ -C ₆ alkoxy. is substituted with one or more substituents selected from the group consisting of;

n is an integer from 1 to 5; am.

More preferably, in Formula 1,

The R ₁ is , , , and It is characterized by being substituted with a substituent selected from the group consisting of.

To illustrate more specifically the compound of Formula 1 of the present invention,

N-(3-((2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2-fluorophenyl)furano[3 ,2-b]pyridine-6-carboxyamide (Compound 1);

N-(3-((2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2-fluorophenyl)-1H-p Rolo[2,3-b]pyridine-5-carboxylamide (Compound 2);

N-(3-((2-bromo-4-perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2-fluorophenyl)-4-chloro- 1H-pyrrolo[2,3-b]pyridine-5-carboxyamide (Compound 3);

N-(3-((2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl-2-fluorophenyl)-2-trifluoro Romethyl)-1,8-naphthyridine-3-carboxyamide (Compound 4); and

N-(3-((2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2-fluorophenyl)-6-chloro -2,3-dihydro-[1,4]deoxyno[2,3-b]pyridine-7-carboxylamide (Compound 5); is selected from the group consisting of

Additionally, the following terms in the present invention have the following meanings unless otherwise indicated. Any undefined terms have meanings understood in the art.

The term “alkyl” refers to a straight-chain or branched-chain hydrocarbon group with a single bond. Examples include methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, and 1-methylpropyl.

The term “alkoxy” refers to an oxygen group to which a single bond of straight or branched saturated hydrocarbon is bonded. Examples include methoxy, ethoxy, propoxy, n-butoxy, tert-butoxy, and 1-methylpropoxy.

The term “halogen” refers to fluorine (F), chlorine (Cl), bromine (Br), and iodine (I).

The term “haloalkyl” refers to an alkyl group substituted by one or more halogen atoms, for example, monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, dichloromethyl, trichloromethyl, mono Bromomethyl, dibromomethyl, tribromomethyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-i-propyl, 2,2-difluoroethyl, 2,2-dichloroethyl , 2,2,2-trifluoroethyl, 1-fluoroethyl, 2-fluoroethyl, 1-chloroethyl, 2-chloroethyl, 1-bromoethyl, 2-bromoethyl, 2-iodo Ethyl, 2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 1,3-difluoro-2-propyl, 1,3-dichloro-2-propyl, 1-chloro-3 -Fluoro-2-propyl, 1,1,1-trifluoro-2-propyl, 2,3,3,3-trifluoro-n-propyl, 1,1,1,3,3,3- Hexafluoro-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-bro Parent-n-propyl, 1,1,2,3,3,3-hexafluoro-1-chloro-n-propyl, 1,1,2,3,3,3-hexafluoro-1-bromo -2-propyl, 2,2,3,3,3-pentafluoro-n-propyl, 3-fluoro-n-propyl, 3-chloro-n-propyl, 3-bromo-n-propyl, etc. there is.

The term “heterocycloalkyl” refers to a ring-shaped, single-bonded saturated hydrocarbon group containing one or more heteroatoms such as N, O, or S, and may vary depending on the number and type of heteroatoms contained in the ring and the number of carbon atoms. Lidinyl, pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, tetrahydrofuranyl, tetrahydropyranyl, etc.

The term “heteroaryl” refers to an aromatic ring compound containing one or more heteroatoms such as N, O, or S, and depending on the number and type of heteroatoms contained in the ring and the number of carbon atoms, pyrrolyl, furanyl, and pyridine. There are days, pyrimidine days, pyran days, etc.

Furthermore, the compounds of the present invention may contain one or more asymmetric carbon atoms and may exist in racemic and optically active forms. All such compounds and diastereomers are included within the scope of the present invention.

In another aspect, the present invention relates to a composition for controlling ticks containing the compound represented by Formula 1 above as an active ingredient, and more preferably to a composition for controlling chicken mites containing the compound represented by Formula 1 above as an active ingredient. It relates to a composition for use.

The composition for controlling ticks may be formulated with various agents known in the art, including the above active ingredients. Specifically, it can be formulated as a solution, emulsion, wettable powder, aqueous suspension, oily suspension, powder, powder, paste, soluble powder, soluble granule, spray granule, aerosol, spray, etc.

The compound represented by Formula 1 may be included in these formulations in an amount of 0.01 to 50% by weight, preferably 0.1 to 30% by weight, depending on the formulation type or formulation method. When formulating, the formulation may include a carrier, emulsifier, and other formulation auxiliaries depending on the formulation type or formulation method.

The carrier may be any carrier known in the art. Suitable solid carriers include, in particular, ammonium salts, and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, finely divided silica, alumina, silicates and the like. Suitable solid carriers for granules are, for example, crushed and fractionated natural rocks such as calcite, marble, pumice, meerschaum and dolomite, and granules of organic materials such as paper, sawdust, coconut shells, corn cobs and tobacco stalks. Suitable liquid carriers include, for example, water, alcohols such as methanol and ethanol, ketones such as acetone and methyl ethyl ketone, benzene, toluene, aromatic hydrocarbons such as xylene and ethylbenzene, hexane and cyclohexane, and kerosene and diesel oil. Aliphatic hydrocarbons, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile and isobutyronitrile, ethers such as diisopropyl ether and dioxane, N,N-dimethylformamide and N,N- Examples include acid amides such as dimethylacetoamide, halogenated hydrocarbons such as dichloromethane and trichloroethane, dimethyl sulfoxide, and vegetable oils such as soybean oil and cottonseed oil. Suitable gas carriers include, for example, butane gas, LPG (liquefied petroleum gas), dimethyl ether, carbon dioxide gas, etc.

Emulsifiers can be either ionic or nonionic emulsifiers. Suitable emulsifiers include alkyl sulfuric acid esters, alkyl sulfonates, alkylaryl sulfonic acids, alkylaryl ethers and their polyoxyethylenates, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives.

Adjuvants for formulations include fixatives and stabilizers. As fixing agents, for example, polysaccharides such as casein, gelatin, starch, starch, gum arabic, cellulose derivatives such as carboxymethyl cellulose, alginic acid, etc.), lignin derivatives, bentonite, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, poly acrylic acids, etc.), etc., and stabilizers include, for example, acidic isopropyl phosphate (PAP), 2,6-di-tert-butyl-4-methylphenol (BHT), and 2-tert-butyl-4-methyl. Examples include a mixture of oxyphenol and 3-tert-butyl-4-methoxyphenol (BHA), vegetable oil, mineral oil, fatty acids and esters thereof.

The composition for controlling ticks of the present invention can be made by spraying, spraying, or applying directly to animals infected with ticks. In this case, the tick control composition of the present invention can be used alone, but it can also be used in combination with other insecticides, nematicides, acaricides, animal feed, etc.

The present invention relates to a novel amide derivative and a composition for controlling ticks containing the same. By introducing a heterocyclic substituent to the amide derivative, a composition for controlling ticks is provided which has an excellent tick control effect compared to an amide derivative with a single ring substituted. can be provided.

Hereinafter, preferred embodiments of the present invention will be described in detail. However, the present invention is not limited to the embodiments described herein and may be embodied in other forms. Rather, the content introduced herein is provided to be thorough and complete, and to fully convey the spirit of the present invention to those skilled in the art.

<Example 1. Synthesis of novel amide derivatives and confirmation of physicochemical properties>

The amide derivative of the present invention was synthesized by referring to the method shown in [Scheme 1] below.

[Scheme 1]

Compound 1. N-(3-((2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2-fluorophenyl)fu Lano[3,2-b]pyridine-6-carboxylamide

Compound 1 was synthesized by the method shown in [Scheme 2] below, and the specific reaction conditions are as follows.

[Scheme 2]

1) Synthesis of 2-fluoro-N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl-3-nitrobenzamide

2-Fluoro-3-nitrobenzoic acid (2.91 g, 15.7mM) and 6 mL of thionyl chloride were mixed with 15 mL of toluene, and 2 drops of dimethylformamide were added dropwise and stirred. The reaction solution was heated to 90°C and stirred for 1 hour, then distilled under reduced pressure to remove the solvent. The acyl chloride obtained from the above process was mixed with (2-bromo-heptafluoropropan-2-yl)-6-(trifluoromethyl)aniline (5.5g, 13.1mM), 1,3-dimethylimidazolidine- 2-one (8.5 ml) and diisopropylamine (6 ml) were added to the mixture, heated to 110°C, and heated to reflux for 3 hours. The reaction solution was then cooled to room temperature, and the organic layer was extracted with ethyl acetate, washed with 1N aqueous hydrogen chloride solution, aqueous sodium carbonate solution, and brine, and then concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (EA: n-hexane = 1:10 ~ 1:5) to obtain 2-fluoro-N-(2-bromo-4-(heptafluoropropan-2-yl) )-6-(trifluoromethyl)phenyl-3-nitrobenzamide (5 g, yield 60%) was obtained.

2) Synthesis of 3-amino-2-fluoro-N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)benzamide

2-Fluoro-N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl-3-nitrobenzamide (4.9 g, 8.5mM) was dissolved in ethanol. After mixing in 40 ml, tin chloride (SnCl2, 4.92g, 25.9mM) was slowly added while cooling the reaction solution. When hydrochloric acid (5.35g, 9.04mM) was slowly added dropwise to the cooled reaction solution, the temperature of the reaction solution decreased. The temperature rises to 50°C, and after about 2 hours, the temperature of the reaction solution is cooled to room temperature, a 10% sodium hydroxide solution is added, and then filtered through Celite. After concentrating the filtrate, the organic layer is extracted with ethyl acetate and dissolved in water. It was washed with oversaturated brine and dried over sodium sulfate. The residue was purified by silica gel column chromatography (ethyl acetate: n-hexane = 1:9 ~ 1:3) to obtain 3-amino-2-fluoro-N-( 4.5 g of 2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)benzamide was obtained.

3) N-(3-((2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)-phenyl)carbamoyl)-2-fluorophenyl)fu Synthesis of lano[3,2-b]pyridine-6-carboxylamide

Mix 5 ml of toluene with furano[3,2-b]pyridine-6-carboxylic acid (100 mg), thionyl chloride (100 ㎕), and 1 drop of N,N-dimethylformamide and incubate at 90°C for 2 hours. It was stirred for a while. The acyl chloride obtained by concentrating the reaction solution was used in the next reaction without further purification. 3-amino-2-fluoro-N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)benzamide ( 300㎎) and furano[3,2-b]pyridine-6-carboxyl chloride were mixed, then 100㎕ of pyridine was added and stirred at room temperature for 16 hours. Water and ethyl acetate were added to the reaction solution, the organic layer was extracted, and then concentrated under reduced pressure. The residue obtained from the above process was purified by silica gel column chromatography (ethyl acetate: n-hexane = 1:9 ~ 1:3) to produce the present invention compound 1 (N-(3-((2-bromo-4-( Perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2-fluorophenyl)furano[3,2-b]pyridine-6-carboxamide) was obtained.

Compound 2. N-(3-((2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2-fluorophenyl)- 1H-pyrrolo[2,3-b]pyridine-5-carboxylamide

[Scheme 3]

The synthesis process of Compound 1 is the same, except that 3-amino-2-fluoro-N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)benz Instead of amide (300 mg) and furano[3,2-b]pyridine-6-carboxyl chloride, 3-amino-2-fluoro-N-(2-bromo-4-(hepta) of [Scheme 3] Fluoropropan-2-yl)-6-(trifluoromethyl)phenyl)benzamide (300 mg) and 1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (100 mg) are used. The present invention compound 2 (N-(3-((2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2-fluoro Phenyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylamide) was obtained.

Compound 3. N-(3-((2-bromo-4-perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2-fluorophenyl)-4 -Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylamide

[Scheme 4]

The synthesis process of Compound 1 is the same, except that 3-amino-2-fluoro-N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)benz Instead of amide (300 mg) and furano[3,2-b]pyridine-6-carboxylchloride, 3-amino-2-fluoro-N-(2-bromo-4-(hepta) of [Scheme 4] Fluoropropan-2-yl)-6-(trifluoromethyl)phenyl)benzamide (300 mg) and 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (100 mg) ㎎) using the present invention compound 3 (N-(3-((2-bromo-4-perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2 -Fluorophenyl)-4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylamide) was obtained.

Compound 4. N-(3-((2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl-2-fluorophenyl)-2 -trifluoromethyl)-1,8-naphthyridine-3-carboxamide

[Scheme 5]

The synthesis process of Compound 1 is the same, except that 3-amino-2-fluoro-N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)benz Instead of amide (300 mg) and furano[3,2-b]pyridine-6-carboxylchloride, 3-amino-2-fluoro-N-(2-bromo-4-(hepta) of [Scheme 5] Fluoropropan-2-yl)-6-(trifluoromethyl)phenyl)benzamide (300 mg) and 2-(trifluoromethyl)-1,8-naphthyridine-3-carboxylic acid (100 mg) ) using the present invention compound 4 (N-(3-((2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl-2- Fluorophenyl)-2-trifluoromethyl)-1,8-naphthyridine-3-carboxamide) was obtained.

Compound 5. N-(3-((2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2-fluorophenyl)- 6-Chloro-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine-7-carboxamide

[Scheme 6]

The synthesis process of Compound 1 is the same, except that 3-amino-2-fluoro-N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)benz Instead of amide (300 mg) and furano[3,2-b]pyridine-6-carboxyl chloride, 3-amino-2-fluoro-N-(2-bromo-4-(hepta) of [Scheme 6] Fluoropropan-2-yl)-6-(trifluoromethyl)phenyl)benzamide (300 mg) and 6-chloro-2,3-dihydro-[1,4-dioxino[2,3- b]-7-carboxylic acid (100 mg) was used to prepare the present invention compound 5 (N-(3-((2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoro Romethyl)phenyl)carbamoyl)-2-fluorophenyl)-6-chloro-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine-7-carboxamide) got it

<Example 2. Confirmation of anti-mite activity>

Insecticidal activity against ticks was confirmed using the compound synthesized in Example 1.

The mites used to confirm anti-mite activity were chicken mites collected from a chicken breeding facility, and the compound of the present invention was dissolved in a 5% acetone aqueous solution at a concentration of 100 ppm and used in the experiment.

The filter paper was immersed in the solution of the present invention compound dissolved in the aqueous acetone solution for 30 seconds and thoroughly dried in the shade. Afterwards, 20 adult mites were placed in Petri dishes (8.8 cm in diameter) lined with filter paper in the shade and stored for 72 hours under light conditions (16:8 hours, 25±1°C) and relative humidity of 50%, and then their activity stopped and they died. The number of mites present was investigated.

The control value of ticks was calculated using Equation 1 below, and the results are listed in Table 1 below. At this time, the control group (untreated group) that was not treated with the compound of the present invention showed a control value of 0%.

[Equation 1]

Control price = (Number of dead ticks/Initial population of ticks) × 100

compound pest control Compound 1 A compound 2 A Compound 3 B Compound 4 B Compound 5 A * A: 72-hour pest control rate is 60~100%
* B: 72-hour pest control rate is 30-60%

As can be seen from the above results, it was confirmed that the composition of the present invention has an excellent control effect against chicken mites.

In addition, it was found that by introducing a heterocyclic substituent, the tick control effect is more selective compared to amide derivatives with a single ring substituted.

Claims (5)

A composition for controlling ticks, characterized in that it contains a compound represented by the following formula (1) or a pharmaceutically acceptable salt thereof:
[Formula 1]

In Formula 1,
R ₁ is , , , and is substituted with a substituent selected from the group consisting of;
R ₂ is substituted with hydrogen or a C ₁ -C ₆ alkyl substituent;
R ₃ is substituted with a halogen substituent;
R ₄ is one selected from the group consisting of hydrogen, hydroxy, halogen, C ₁ -C ₆ haloalkyl, S-(C ₁ -C ₆ alkyl), C ₁ -C ₆ alkyl and C ₁ -C ₆ alkoxy. is substituted with one or more of the substituents;
n is an integer from 1 to 5; am. delete According to paragraph 1,
The compound of Formula 1 is
N-(3-((2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2-fluorophenyl)furano[3 ,2-b]pyridine-6-carboxyamide (Compound 1);
N-(3-((2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2-fluorophenyl)-1H-p Rolo[2,3-b]pyridine-5-carboxylamide (Compound 2);
N-(3-((2-bromo-4-perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2-fluorophenyl)-4-chloro- 1H-pyrrolo[2,3-b]pyridine-5-carboxyamide (Compound 3);
N-(3-((2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl-2-fluorophenyl)-2-trifluoro Romethyl)-1,8-naphthyridine-3-carboxyamide (Compound 4); and
N-(3-((2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2-fluorophenyl)-6-chloro -2,3-dihydro-[1,4]deoxyno[2,3-b]pyridine-7-carboxylamide (Compound 5);
A composition for controlling ticks, characterized in that selected from the group consisting of. delete According to paragraph 1,
A composition for controlling ticks, wherein the ticks are chicken ticks.