Novel condensed heterocyclic amide compound and pest control agent

Abstract

To provide a novel agent having superior pest control effect.SOLUTION: The present invention relates to a condensed heterocyclic amide compound represented by formula (1), or a salt thereof, wherein in formula (1), Q represents Q-3 and the like; J represents J-2 and the like; G represents G-3 and the like; R3 represents a hydrogen atom and the like; Y represents an oxygen atom and the like; Z1 represents a halogen atom and the like; Z2 represents a halogen atom and the like; and t4 represents an integer of 0, 1, 2, 3, or 4.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to novel condensed heterocyclic amide compounds and salts thereof, production intermediates thereof, and pest control agents, agricultural chemicals, control agents, insecticides, acaricides, seed treatment agents, and soil treatment agents containing the compounds and / or salts thereof as active ingredients.

Background Art

[0002] Certain heterocyclic amide compounds are known to exhibit pest control activity (for example, Patent Documents 1 and 2). Also, methods for synthesizing certain condensed heterocyclic amide compounds are known (for example, Non-Patent Document 1).

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Patent Document 2

Non-Patent Documents

[0004]

Non-Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0005] However, the long-term use of drugs can cause the emergence of pests and harmful organisms that have acquired resistance to existing insecticides. Therefore, the development of new drugs with excellent pest control effects has always been expected.

Means for Solving the Problems

[0006] As a result of intensive studies aimed at solving the above problems, the present inventors have found that a novel condensed heterocyclic amide compound represented by the following formula (1) according to the present invention exhibits excellent pest control activity, particularly excellent activity against insects and mites, and have completed the present invention.

[0007] That is, the present invention relates to a condensed heterocyclic amide compound represented by the following formula (1) or a salt thereof.

[0008] Formula (1):

[0009] [Chemical formula]

[0010] [In the formula, Q represents Q-1, Q-2, Q-3, Q-4, Q-6, Q-8, Q-9, Q-10, Q-12a or Q-47a,

[0011] [Chemical formula]

[0012] Z 1 represents a halogen atom, C 1 ~C 6 alkyl, halo(C 1 ~C 6 )alkyl, C 1 ~C 6 alkoxy or cyano, J represents J-1 or J-2,

[0013] [Chemical formula]

[0014] G represents G-1, G-2, G-3 or G-7,

[0015] [Chemical formula]

[0016] Z 2 is a halogen atom, C 1 ~C 6 alkyl or halo(C 1 ~C 6 )alkyl, and R 1 is a hydrogen atom, a halogen atom or halo(C 1 ~C 6 )alkyl, and R 3 represents a hydrogen atom, and Y represents an oxygen atom or a sulfur atom, and t2 represents an integer of 0, 1 or 2, and t3 represents an integer of 0, 1, 2 or 3, and t4 represents an integer of 0, 1, 2, 3 or 4, and t5 represents an integer of 0, 1, 2, 3, 4 or 5.).

Advantages of the Invention

[0017] The compound according to the present invention represented by formula (1) exhibits excellent insecticidal and acaricidal activities against many agricultural pests, mites, internal or external parasites of mammals or birds. Therefore, the present invention can provide a novel condensed heterocyclic amide compound or a salt thereof that is useful as a pest control agent, particularly as an insecticide.

Modes for Carrying Out the Invention

[0018] In the compound according to the present invention represented by formula (1) (hereinafter also referred to as "the compound of the present invention"), depending on the type of substituents, geometric isomers of the E-form and Z-form may exist, and the compound of the present invention includes these E-forms, Z-forms or a mixture containing the E-form and Z-form in any ratio.

[0019] In addition, the compound of the present invention has optically active forms due to the presence of one or more asymmetric carbon atoms or asymmetric sulfur atoms, and the compound of the present invention includes all optically active forms or racemates.

[0020] In addition, depending on the type of substituent, the compounds of the present invention may have tautomers, and the compounds of the present invention include all tautomers or mixtures of tautomers containing them in any ratio.

[0021] In addition, due to restricted bond rotation caused by steric hindrance between substituents, the compounds of the present invention may exist as one or more rotational isomers, and the compounds of the present invention include all rotational isomers or mixtures of diastereomers containing them in any ratio.

[0022] Among the compounds of the present invention, those that can be converted into salts according to conventional methods include, for example, salts of hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, and hydroiodic acid, salts of inorganic acids such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, and perchloric acid, salts of sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, and p-toluenesulfonic acid, salts of carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, and citric acid, salts of amino acids such as glutamic acid and aspartic acid, salts of alkali metals such as lithium, sodium, and potassium, salts of alkaline earth metals such as calcium, barium, and magnesium, salts of aluminum, and quaternary ammonium salts such as tetramethylammonium salts, tetrabutylammonium salts, and benzyltrimethylammonium salts.

[0023] Next, specific examples of each substituent shown in this specification are shown below. Here, n- means normal, i- means iso, s- means secondary, and tert- means tertiary, respectively.

[0024] Examples of the "halogen atom" in this specification include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. In addition, the notation "halo" in this specification also represents these halogen atoms.

[0025] "C a ~C bThe notation "alkyl" represents a linear or branched hydrocarbon group consisting of a to b carbon atoms. Specific examples include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl, n-hexyl, etc., and they are selected within the range of the specified number of carbon atoms for each.

[0026] As used herein, "halo(C a ~C b )alkyl" represents a linear or branched hydrocarbon group consisting of a to b carbon atoms in which the hydrogen atoms bonded to the carbon atoms are arbitrarily substituted by halogen atoms. In this case, when the alkyl group is substituted by two or more halogen atoms, those halogen atoms may be the same as or different from each other. Specific examples include fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, trichloromethyl, bromodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2,2-trichloroethyl, 2-bromo-2,2-difluoroethyl, 1,1,2,2-tetrafluoroethyl, 2-chloro-1,1,2-trifluoroethyl, 2-chloro-1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 2,2-difluoropropyl, 3,3,3-trifluoropropyl, 3-bromo-3,3-difluoropropyl, 2,2,3,3-tetrafluoropropyl, 2,2,3,3,3-pentafluoropropyl, 1,1,2,3,3,3-hexafluoropropyl, heptafluoropropyl, 2,2,2-trifluoro-1-(methyl)ethyl, 2,2,2-trifluoro-1-(trifluoromethyl)ethyl, 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl, 2,2,3,4,4,4-hexafluorobutyl, 2,2,3,3,4,4,4-heptafluorobutyl, nonafluorobutyl, etc., and they are selected within the range of the specified number of carbon atoms for each.

[0027] In this specification, the notation "C a ~C b alkoxy" represents an alkyl-O-group having the above-mentioned meaning and consisting of a to b carbon atoms. Specific examples include methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butyloxy, i-butyloxy, s-butyloxy, tert-butyloxy, 2-ethylhexyloxy, etc., and they are each selected within the specified range of the number of carbon atoms.

[0028] In this specification, the notation "C a ~C b alkoxycarbonyl" represents an alkyl-O-C(O)-group having the above-mentioned meaning and consisting of a to b carbon atoms. Specific examples include methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, i-propyloxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, s-butoxycarbonyl, tert-butoxycarbonyl, 2-ethylhexyloxycarbonyl, etc., and they are each selected within the specified range of the number of carbon atoms.

[0029] Next, the method for producing the compound of the present invention represented by formula (1) will be described below. The compound of the present invention can be produced, for example, by the following method. Note that the following description is merely illustrative, and the compound of the present invention represented by formula (1) may be produced by other methods. Hereinafter, "the compound of the present invention represented by formula (1)" is also referred to as "the compound of the present invention (1)", and "the compound represented by formula (2)" is also referred to as "compound (2)". The same applies to other compounds.

[0030] [Production Method 1] The compound of the present invention (1) can be produced by reacting compound (2) with compound (3).

[0031] [Chemical Formula] (In the formula, Xa represents a chlorine atom or a bromine atom, and J, Q, G, Y, and R3 represents the same meaning as described above.)

[0032] Compound (1) can be produced by reacting compound (2) and compound (3) in a solvent or without a solvent.

[0033] As the equivalent of compound (3) to be used, it can be used in the range of 1 to 50 equivalents, preferably in the range of 1 to 20 equivalents, relative to 1 equivalent of compound (2).

[0034] When using a solvent, the solvent to be used may be inert to the reaction. For example, water, alcohol solvents such as methanol and ethanol, ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, and 1,2-dimethoxyethane, aromatic hydrocarbon solvents such as benzene, xylene, and toluene, aliphatic hydrocarbon solvents such as pentane, hexane, and cyclohexane, halogenated hydrocarbon solvents such as dichloromethane, chloroform, and 1,2-dichloroethane, nitrile solvents such as acetonitrile and propionitrile, amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and N,N'-dimethylimidazolidinone, dimethyl sulfoxide, or a mixed solvent thereof, etc. can be mentioned.

[0035] The reaction can also be carried out using a base. Examples of the base that can be used include organic bases such as pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), 1,5-diazabicyclo[4.3.0]-5-nonene (DBN), etc., inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate, cesium carbonate, potassium phosphate, etc., and metal alkoxides such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc. The amount of the base used (equivalent) can be used in the range of 0.1 to 100 equivalents relative to 1 equivalent of compound (2).

[0036] The reaction temperature can be set arbitrarily from -80°C to the reflux temperature of the reaction mixture, and a range from 0°C to the reflux temperature of the reaction mixture is preferred.

[0037] The reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be arbitrarily set within the range of 5 minutes to 100 hours, and a range of 1 hour to 48 hours is preferred.

[0038] In the reaction of Production Method 1, after the reaction is completed, the reaction mixture can be subjected to ordinary post-treatments such as direct concentration, or dissolution in an organic solvent followed by washing with water and then concentration, or pouring into ice water followed by extraction with an organic solvent and then concentration, to obtain the target compound of the present invention. Also, when purification is required, it can be separated and purified by any purification method such as recrystallization, column chromatography, thin-layer chromatography, preparative liquid chromatography, etc.

[0039] Compound (2) used in Production Method 1 can be produced according to the following production process.

[0040] [Production Step 1] Compound (2) can be produced by reacting compound (3) and compound (4) in a solvent or without a solvent.

[0041]

Chemical formula

[0042] (In the formula, Ja represents Ja-1 or Ja-2,

[0043]

Chemical formula

[0044] J, Q, G, Y, R 1 , and R 3represents the same meaning as described above, Ga represents a halogen atom or the like, and Gb represents a leaving group such as B(OH) 2 (etc.).)

[0045] When using a solvent, the solvent used may be inert to the reaction, and examples thereof include the solvents exemplified in Production Method 1.

[0046] This reaction can also be carried out using a base. Examples of the base that can be used include organic bases such as pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), 1,5-diazabicyclo[4.3.0]-5-nonene (DBN), etc., inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate, cesium carbonate, potassium phosphate, etc., and metal alkoxides such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc. The usage amount (equivalent) of the base can be used in an amount of 0.1 to 100 equivalents relative to 1 equivalent of compound (3).

[0047] This reaction can be carried out in the presence of a palladium catalyst. Examples of the palladium catalyst include [1,1'-bis(diphenylphosphino)ferrocene]palladium (divalent) dichloride dichloromethane adduct, etc. The usage amount of the palladium catalyst can be used in an amount of 0.005 to 20 equivalents relative to 1 equivalent of compound (3).

[0048] This reaction can be carried out in the presence of a ligand. Examples of the ligand include 1,1'-bis(diphenylphosphino)ferrocene, etc. The usage amount of the ligand can be used in an amount of 0.005 to 20 equivalents relative to 1 equivalent of compound (3).

[0049] The reaction temperature can be set to any temperature from -78 °C to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be arbitrarily set within the range of 5 minutes to 100 hours.

[0050] Compound (3) can be produced according to a known method described in the literature, for example, the method described in International Publication No. 2021 / 261562 etc.

[0051] Some of compound (4) are known compounds and some are commercially available. The others can also be produced according to the synthesis method of known compounds.

[0052] [Production Step 2] Compound (2) can be produced by reacting compound (5) with compound (6).

[0053] [Chemical Formula]

[0054] (In the formula, J, Q, Y, and R 3 represent the same meaning as described above, and Qa is C 1 ~C 6 represents an alkoxy group.)

[0055] Compound (2) can be produced by reacting compound (5) with compound (6) in a solvent or without a solvent.

[0056] When using a solvent, the solvent used may be inert to the reaction, and examples include the solvents exemplified in Production Method 1.

[0057] This reaction can also be carried out using a base. Examples of the base that can be used include the bases exemplified in Production Method 1. The amount of the base used (equivalent) can be 0.1 to 100 equivalents relative to 1 equivalent of compound (5).

[0058] The reaction temperature can be set to any temperature from -78 °C to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be arbitrarily set within the range of 5 minutes to 100 hours.

[0059] Compound (5) can be produced according to a known method in the literature, for example, the method described in International Publication No. 2021 / 261562, etc.

[0060] Some of compound (6) are known compounds, and some are available as commercial products. Others can also be produced according to the synthesis method of known compounds.

[0061] [Production Step 3] Among compound (2), the compound (2a) in which J represents J-2 can be produced by reacting compound (7).

[0062] [Chemical Formula]

[0063] (In the formula, Q, G, Y, and R 3 represent the same meaning as described above.)

[0064] Compound (2a) can be produced by reacting compound (7) in a solvent or without a solvent.

[0065] When using a solvent, the solvent used may be inert to the reaction, for example, the solvents exemplified in Production Method 1.

[0066] This reaction can also be carried out using a base. Examples of the base that can be used include the bases exemplified in Production Method 1. The usage amount (equivalent) of the base can be 0.1 to 100 equivalents relative to 1 equivalent of compound (7).

[0067] The reaction temperature can be set to any temperature from -78°C to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be arbitrarily set within the range of 5 minutes to 100 hours.

[0068] Compound (7) used in Production Step 3 can be produced according to the following reaction formula.

[0069] [Production Step 4]

[0070] [Chemical Formula]

[0071] (In the formula, Q, G, Y, and R 3 represent the same meanings as described above, and Jb is C 1 ~C 6 represents alkyl.)

[0072] [Step 1] Compound (9) can be produced by reacting compound (10) with compound (6) according to a known method described in the literature, for example, the method described in International Publication No. 2016 / 118611, etc.

[0073] Some of compound (10) are known compounds and some are commercially available. Others can also be produced according to a known method described in the literature, for example, the method described in The Journal of Organic Chemistry 2004, Vol. 69, pp. 130 - 141.

[0074] [Step 2] Compound (8) can be produced by reacting compound (9) according to a known method described in the literature, for example, the method described in The Journal of Organic Chemistry 2006, Vol. 24, pp. 9045 - 9050.

[0075] [Project 3] Compound (7) can be produced by reacting compound (8) with compound (11) according to a known method in the literature, for example, the method described in Synthetic Communications 2006, Vol. 36, pp. 729-741.

[0076] Some of compound (11) are known compounds and some are commercially available. Others can also be produced according to a known method described in the literature, for example, the method described in Bioorganic & Medicinal Chemistry 2018, Vol. 26, pp. 1713-1726.

[0077] In the reactions of Production Steps 1 to 4, after the reaction is completed, the reaction mixture can be subjected to ordinary post-treatments such as direct concentration, or dissolution in an organic solvent followed by washing with water and then concentration, or pouring into ice water followed by extraction with an organic solvent and then concentration, to obtain the target compound of the present invention. When purification is required, it can be separated and purified by any purification method such as recrystallization, column chromatography, thin-layer chromatography, preparative liquid chromatography, etc.

[0078] Examples of the compounds of the present invention that can be produced using these methods and the production intermediates of the compounds of the present invention include the compounds shown in Tables 1 to 2.

[0079] In addition, the descriptions of Q-1, Q-2, Q-3, Q-4, Q-6, Q-8, Q-9, Q-10, Q-12a and Q-47a in the table represent the following structures.

Chemical formula

[0080] In addition, the descriptions of G-1, G-2, G-3 and G-7 in the table represent the following structures respectively.

Chemical formula

[0081] Furthermore, the numbers shown in the above structural formula represent the substitution positions of the substituents (Z 1 ) t2 , (Z 1 ) t3 , (Z 1 ) t4 , (Z 1 ) t5 , (Z 2 ) t4 or (Z 2 ) t5 . For example, in the table, "Q-1(4-F)" represents "4-fluorophenyl", and "Q-1" represents "phenyl".

[0082] [Table 1]

Chemical formula

[0083] ―――――――――――――――― Q G ―――――――――――――――― Q-3(3-Cl) G-1(4-F) Q-3(3-Cl) G-1(2-F) Q-3(3-Cl) G-1(2-Cl) Q-3(3-Cl) G-3(3-F) Q-3(3-Cl) G-3(3-Cl) Q-3(3-Cl) G-3(3-CH 3 ) Q-3(3-Cl) G-3(3-CF 3 ) Q-3(3-CH 3 ) G-1(4-F) Q-3(3-CH 3 ) G-1(2-F) Q-3(3-CH 3 ) G-1(2-Cl) Q-3(3-CH 3 ) G-3(3-F) Q-3(3-CH 3 ) G-3(3-Cl) Q-3(3-CH 3 ) G-3(3-CH 3 ) Q-3(3-CH 3 ) G-3(3-CF 3 ) Q-4(3-Cl) G-1(4-F) Q-4(3-Cl) G-1(2-F) Q-4(3-Cl) G-1(2-Cl) Q-4(3-Cl) G-3(3-F) Q-4(3-Cl) G-3(3-Cl) Q-4(3-Cl) G-3(3-CH 3 ) Q-4(3-Cl) G-3(3-CF 3 ) Q-4(3-CH 3 ) G-1(4-F) Q-4(3-CH 3 ) G-1(2-F) Q-4(3-CH 3 ) G-1(2-Cl) Q-4(3-CH 3 ) G-3(3-F) Q-4(3-CH 3 ) G-3(3-Cl) Q-4(3-CH 3 ) G-3(3-CH 3 ) Q-4(3-CH 3 ) G-3(3-CF 3 ) Q-4(4-CH 3 ) G-1(4-F) Q-4(4-CH 3 ) G-1(2-F) Q-4(4-CH 3 ) G-1(2-Cl) Q-4(4-CH 3 ) G-3(3-F) Q-4(4-CH 3 ) G-3(3-Cl) Q-4(4-CH 3 ) G-3(3-CH 3 ) Q-4(4-CH 3) G-3(3-CF 3 ) Q-4(3-Br) G-1(4-F) Q-4(3-Br) G-1(2-F) Q-4(3-Br) G-1(2-Cl) Q-4(3-Br) G-3(3-F) Q-4(3-Br) G-3(3-Cl) Q-4(3-Br) G-3(3-CH 3 ) Q-4(3-Br) G-3(3-CF 3 ) Q-10(3-CH 3 ) G-1(4-F) Q-10(3-CH 3 ) G-1(2-F) Q-10(3-CH 3 ) G-1(2-Cl) Q-10(3-CH 3 ) G-3(3-F) Q-10(3-CH 3 ) G-3(3-Cl) Q-10(3-CH 3 ) G-3(3-CH 3 ) Q-10(3-CH 3 ) G-3(3-CF 3 ) Q-12a G-1(4-F) Q-12a G-1(2-F) Q-12a G-1(2-Cl) Q-12a G-3(3-F) Q-12a G-3(3-Cl) Q-12a G-3(3-CH 3 ) Q-12a G-3(3-CF 3 ) Q-47a G-1(4-F) Q-47a G-1(2-F) Q-47a G-1(2-Cl) Q-47a G-3(3-F) Q-47a G-3(3-Cl) Q-47a G-3(3-CH3 ) Q-47a G-3(3-CF 3 ) Q-3(4-CN) G-1(4-F) Q-3(4-CN) G-1(2-F) Q-3(4-CN) G-1(2-Cl) Q-3(4-CN) G-3(3-F) Q-3(4-CN) G-3(3-Cl) Q-3(4-CN) G-3(3-CH 3 ) Q-3(4-CN) G-3(3-CF 3 ) Q-2(4-CN) G-1(4-F) Q-2(4-CN) G-1(2-F) Q-2(4-CN) G-1(2-Cl) Q-2(4-CN) G-3(3-F) Q-2(4-CN) G-3(3-Cl) Q-2(4-CN) G-3(3-CH 3 ) Q-2(4-CN) G-3(3-CF 3 ) Q-3(5-Cl) G-1(4-F) Q-3(5-Cl) G-1(2-F) Q-3(5-Cl) G-1(2-Cl) Q-3(5-Cl) G-3(3-F) Q-3(5-Cl) G-3(3-Cl) Q-3(5-Cl) G-3(3-CH 3 ) Q-3(5-Cl) G-3(3-CF 3 ) Q-3(5-CH 3 ) G-1(4-F) Q-3(5-CH 3 ) G-1(2-F) Q-3(5-CH 3 ) G-1(2-Cl) Q-3(5-CH 3 ) G-3(3-F) Q-3(5-CH3 ) G-3(3-Cl) Q-3(5-CH 3 ) G-3(3-CH 3 ) Q-3(5-CH 3 ) G-3(3-CF 3 ) Q-6(3-CH 3 ) G-1(4-F) Q-6(3-CH 3 ) G-1(2-F) Q-6(3-CH 3 ) G-1(2-Cl) Q-6(3-CH 3 ) G-3(3-F) Q-6(3-CH 3 ) G-3(3-Cl) Q-6(3-CH 3 ) G-3(3-CH 3 ) Q-6(3-CH 3 ) G-3(3-CF 3 ) Q-6(3-Cl) G-1(4-F) Q-6(3-Cl) G-1(2-F) Q-6(3-Cl) G-1(2-Cl) Q-6(3-Cl) G-3(3-F) Q-6(3-Cl) G-3(3-Cl) Q-6(3-Cl) G-3(3-CH 3 ) Q-6(3-Cl) G-3(3-CF 3 ) Q-3(4-I) G-1(4-F) Q-3(4-I) G-1(2-F) Q-3(4-I) G-1(2-Cl) Q-3(4-I) G-3(3-F) Q-3(4-I) G-3(3-Cl) Q-3(4-I) G-3(3-CH 3 ) Q-3(4-I) G-3(3-CF 3 ) Q-10 G-1(4-F) Q-10 G-1(2-F) Q-10 G-1(2-Cl) Q-10 G-3(3-F) Q-10 G-3(3-Cl) Q-10 G-3(3-CH 3 ) Q-10 G-3(3-CF 3 ) Q-3(5-Br) G-1(4-F) Q-3(5-Br) G-1(2-F) Q-3(5-Br) G-1(2-Cl) Q-3(5-Br) G-3(3-F) Q-3(5-Br) G-3(3-Cl) Q-3(5-Br) G-3(3-CH 3 ) Q-3(5-Br) G-3(3-CF 3 ) Q-3(3-Br) G-1(4-F) Q-3(3-Br) G-1(2-F) Q-3(3-Br) G-1(2-Cl) Q-3(3-Br) G-3(3-F) Q-3(3-Br) G-3(3-Cl) Q-3(3-Br) G-3(3-CH 3 ) Q-3(3-Br) G-3(3-CF 3 ) Q-3(4-CF 3 ) G-1(4-F) Q-3(4-CF 3 ) G-1(2-F) Q-3(4-CF 3 ) G-1(2-Cl) Q-3(4-CF 3 ) G-3(3-F) Q-3(4-CF 3 ) G-3(3-Cl) Q-3(4-CF 3 ) G-3(3-CH 3 ) Q-3(4-CF 3 ) G-3(3-CF3 ) Q-8(3-CH 3 ) G-1(4-F) Q-8(3-CH 3 ) G-1(2-F) Q-8(3-CH 3 ) G-1(2-Cl) Q-8(3-CH 3 ) G-3(3-F) Q-8(3-CH 3 ) G-3(3-Cl) Q-8(3-CH 3 ) G-3(3-CH 3 ) Q-8(3-CH 3 ) G-3(3-CF 3 ) Q-8(3-Cl) G-1(4-F) Q-8(3-Cl) G-1(2-F) Q-8(3-Cl) G-1(2-Cl) Q-8(3-Cl) G-3(3-F) Q-8(3-Cl) G-3(3-Cl) Q-8(3-Cl) G-3(3-CH 3 ) Q-8(3-Cl) G-3(3-CF 3 ) Q-1(4-F) G-1(4-F) Q-1(4-F) G-1(5-F) Q-1(4-F) G-3(3-F) Q-1(4-F) G-3(3-Cl) Q-1(4-F) G-3(3-CH 3 ) Q-1(4-F) G-3(3-CF 3 ) Q-1(4-CN) G-1(4-F) Q-1(4-CN) G-1(5-F) Q-1(4-CN) G-3(3-F) Q-1(4-CN) G-3(3-Cl) Q-1(4-CN) G-3(3-CH 3 ) Q-1(4-CN) G-3(3-CF 3 ) Q-2(4-F) G-1(4-F) Q-2(4-F) G-1(5-F) Q-2(4-F) G-3(3-F) Q-2(4-F) G-3(3-Cl) Q-2(4-F) G-3(3-CH 3 ) Q-2(4-F) G-3(3-CF 3 ) Q-2(4-Cl) G-1(4-F) Q-2(4-Cl) G-1(5-F) Q-2(4-Cl) G-3(3-F) Q-2(4-Cl) G-3(3-Cl) Q-2(4-Cl) G-3(3-CH 3 ) Q-2(4-Cl) G-3(3-CF 3 ) Q-2(4-CN) G-1(5-F) Q-3 G-1(4-F) Q-3 G-1(5-F) Q-3 G-3(3-F) Q-3 G-3(3-Cl) Q-3 G-3(3-CH 3 ) Q-3 G-3(3-CF 3 ) Q-3(3-CH 3 ) G-1(5-F) Q-3(3-Cl) G-1(5-F) Q-3(3-F) G-1(4-F) Q-3(3-F) G-1(5-F) Q-3(3-F) G-3(3-F) Q-3(3-F) G-3(3-Cl) Q-3(3-F) G-3(3-CH 3 ) Q-3(3-F) G-3(3-CF 3 ) Q-3(4-Br) G-1(4-F) Q-3(4-Br) G-1(5-F) Q-3(4-Br) G-3(3-F) Q-3(4-Br) G-3(3-Cl) Q-3(4-Br) G-3(3-CH 3 ) Q-3(4-Br) G-3(3-CF 3 ) Q-3(4-CF 3 ) G-1(5-F) Q-3(4-CH 3 ) G-1(4-F) Q-3(4-CH 3 ) G-1(5-F) Q-3(4-CH 3 ) G-3(3-F) Q-3(4-CH 3 ) G-3(3-Cl) Q-3(4-CH 3 ) G-3(3-CH 3 ) Q-3(4-CH 3 ) G-3(3-CF 3 ) Q-3(4-Cl) G-1(4-F) Q-3(4-Cl) G-1(5-F) Q-3(4-Cl) G-3(3-F) Q-3(4-Cl) G-3(3-Cl) Q-3(4-Cl) G-3(3-CH 3 ) Q-3(4-Cl) G-3(3-CF 3 ) Q-3(4-CN) G-1(5-F) Q-3(4-F) G-1(4-F) Q-3(4-F) G-1(5-F) Q-3(4-F) G-3(3-F) Q-3(4-F) G-3(3-Cl) Q-3(4-F) G-3(3-CH 3 ) Q-3(4-F) G-3(3-CF 3 ) Q-3(6-F) G-1(4-F) Q-3(6-F) G-1(5-F) Q-3(6-F) G-3(3-F) Q-3(6-F) G-3(3-Cl) Q-3(6-F) G-3(3-CH 3 ) Q-3(6-F) G-3(3-CF 3 ) Q-4 G-1(4-F) Q-4 G-1(5-F) Q-4 G-3(3-F) Q-4 G-3(3-Cl) Q-4 G-3(3-CH 3 ) Q-4 G-3(3-CF 3 ) Q-4(3-CH 3 ) G-1(5-F) Q-4(3-Cl) G-1(5-F) Q-4(4-Br) G-1(4-F) Q-4(4-Br) G-1(5-F) Q-4(4-Br) G-3(3-F) Q-4(4-Br) G-3(3-Cl) Q-4(4-Br) G-3(3-CH 3 ) Q-4(4-Br) G-3(3-CF 3 ) Q-4(4-Cl) G-1(4-F) Q-4(4-Cl) G-1(5-F) Q-4(4-Cl) G-3(3-F) Q-4(4-Cl) G-3(3-Cl) Q-4(4-Cl) G-3(3-CH 3 ) Q-4(4-Cl) G-3(3-CF 3 ) Q-6(4-Cl) G-1(4-F) Q-6(4-Cl) G-1(5-F) Q-6(4-Cl) G-3(3-F) Q-6(4-Cl) G-3(3-Cl) Q-6(4-Cl) G-3(3-CH 3 ) Q-6(4-Cl) G-3(3-CF 3 ) Q-9 G-1(4-F) Q-9 G-1(5-F) Q-9 G-3(3-F) Q-9 G-3(3-Cl) Q-9 G-3(3-CH 3 ) Q-9 G-3(3-CF 3 ) Q-12a G-1(5-F) ―――――――――――――――― [Table 2]

Chem.

[0084] ―――――――――――――――― R 1 Q G ―――――――――――――――― CHF 2 Q-1(3-F) G-1(4-F) CHF 2 Q-1(3-F) G-3(3-F) CHF 2 Q-1(3-F) G-3(3-Cl) CHF 2 Q-1(3-F) G-3(3-CH 3 ) CHF 2 Q-1(3-F) G-3(3-CF 3 ) CHF 2 Q-1(4-F) G-1(4-F) CHF 2 Q-1(4-F) G-3(3-F) CHF 2 Q-1(4-F) G-3(3-Cl) CHF 2 Q-1(4-F) G-3(3-CH 3 ) CHF 2Q-1(4-F) G-3(3-CF 3 ) CHF 2 Q-1(4-CN) G-1(4-F) CHF 2 Q-1(4-CN) G-3(3-F) CHF 2 Q-1(4-CN) G-3(3-Cl) CHF 2 Q-1(4-CN) G-3(3-CH 3 ) CHF 2 Q-1(4-CN) G-3(3-CF 3 ) CHF 2 Q-1(4-CF 3 ) G-1(4-F) CHF 2 Q-1(4-CF 3 ) G-3(3-F) CHF 2 Q-1(4-CF 3 ) G-3(3-Cl) CHF 2 Q-1(4-CF 3 ) G-3(3-CH 3 ) CHF 2 Q-1(4-CF 3 ) G-3(3-CF 3 ) CHF 2 Q-1(2-F,4-F) G-1(4-F) CHF 2 Q-1(2-F,4-F) G-3(3-F) CHF 2 Q-1(2-F,4-F) G-3(3-Cl) CHF 2 Q-1(2-F,4-F) G-3(3-CH 3 ) CHF 2 Q-1(2-F,4-F) G-3(3-CF 3 ) CHF 2 Q-1(3-F,4-F) G-1(4-F) CHF 2Q-1(3-F,4-F) G-3(3-F) CHF 2 Q-1(3-F,4-F) G-3(3-Cl) CHF 2 Q-1(3-F,4-F) G-3(3-CH 3 ) CHF 2 Q-1(3-F,4-F) G-3(3-CF 3 ) CHF 2 Q-2(4-F) G-1(4-F) CHF 2 Q-2(4-F) G-3(3-F) CHF 2 Q-2(4-F) G-3(3-Cl) CHF 2 Q-2(4-F) G-3(3-CH 3 ) CHF 2 Q-2(4-F) G-3(3-CF 3 ) CHF 2 Q-3 G-1(4-F) CHF 2 Q-3 G-3(3-F) CHF 2 Q-3 G-3(3-Cl) CHF 2 Q-3 G-3(3-CH 3 ) CHF 2 Q-3 G-3(3-CF 3 ) CHF 2 Q-3(4-F) G-1(4-F) CHF 2 Q-3(4-F) G-3(3-F) CHF 2 Q-3(4-F) G-3(3-Cl) CHF 2 Q-3(4-F) G-3(3-CH 3 ) CHF 2 Q-3(4-F) G-3(3-CF 3 ) CHF 2 Q-3(4-Cl) G-1(4-F) CHF 2 Q-3(4-Cl) G-3(3-F) CHF 2 Q-3(4-Cl) G-3(3-Cl) CHF 2 Q-3(4-Cl) G-3(3-CH 3 ) CHF 2 Q-3(4-Cl) G-3(3-CF 3 ) CHF 2 Q-3(4-CH 3 ) G-1(4-F) CHF 2 Q-3(4-CH 3 ) G-3(3-F) CHF 2 Q-3(4-CH 3 ) G-3(3-Cl) CHF 2 Q-3(4-CH 3 ) G-3(3-CH 3 ) CHF 2 Q-3(4-CH 3 ) G-3(3-CF 3 ) CHF 2 Q-3(3-CH 3 ) G-1(4-F) CHF 2 Q-3(3-CH 3 ) G-3(3-F) CHF 2 Q-3(3-CH 3 ) G-3(3-Cl) CHF 2 Q-3(3-CH 3 ) G-3(3-CH 3 ) CHF 2 Q-3(3-CH 3 ) G-3(3-CF 3 ) CHF 2 Q-3(3-OCH 3 ) G-1(4-F) CHF 2 Q-3(3-OCH 3 ) G-3(3-F) CHF 2 Q-3(3-OCH 3 ) G-3(3-Cl) CHF 2 Q-3(3-OCH 3 ) G-3(3-CH 3 ) CHF 2 Q-3(3-OCH 3 ) G-3(3-CF 3 ) CHF 2 Q-4 G-1(4-F) CHF 2 Q-4 G-3(3-F) CHF 2 Q-4 G-3(3-Cl) CHF 2 Q-4 G-3(3-CH 3 ) CHF 2 Q-4 G-3(3-CF 3 ) CHF 2 Q-4(4-CH 3 ) G-1(4-F) CHF 2 Q-4(4-CH 3 ) G-3(3-F) CHF 2 Q-4(4-CH 3 ) G-3(3-Cl) CHF 2 Q-4(4-CH 3 ) G-3(3-CH 3 ) CHF 2 Q-4(4-CH 3 ) G-3(3-CF 3 ) CHF 2 Q-4(3-CH 3 ) G-1(4-F) CHF 2 Q-4(3-CH 3 ) G-3(3-F) CHF 2 Q-4(3-CH 3 ) G-3(3-Cl) CHF 2 Q-4(3-CH3 ) G-3(3-CH 3 ) CHF 2 Q-4(3-CH 3 ) G-3(3-CF 3 ) CHF 2 Q-9 G-1(4-F) CHF 2 Q-9 G-3(3-F) CHF 2 Q-9 G-3(3-Cl) CHF 2 Q-9 G-3(3-CH 3 ) CHF 2 Q-9 G-3(3-CF 3 ) CHF 2 Q-12a G-1(4-F) CHF 2 Q-12a G-3(3-F) CHF 2 Q-12a G-3(3-Cl) CHF 2 Q-12a G-3(3-CH 3 ) CHF 2 Q-12a G-3(3-CF 3 ) CF 3 Q-1(3-F) G-1(4-F) CF 3 Q-1(3-F) G-3(3-F) CF 3 Q-1(3-F) G-3(3-Cl) CF 3 Q-1(3-F) G-3(3-CH 3 ) CF 3 Q-1(3-F) G-3(3-CF 3 ) CF 3 Q-1(4-F) G-1(4-F) CF 3 Q-1(4-F) G-3(3-F) CF 3 Q-1(4-F) G-3(3-Cl) CF3 Q-1(4-F) G-3(3-CH 3 ) CF 3 Q-1(4-F) G-3(3-CF 3 ) CF 3 Q-1(4-CN) G-1(4-F) CF 3 Q-1(4-CN) G-3(3-F) CF 3 Q-1(4-CN) G-3(3-Cl) CF 3 Q-1(4-CN) G-3(3-CH 3 ) CF 3 Q-1(4-CN) G-3(3-CF 3 ) CF 3 Q-1(4-CF 3 ) G-1(4-F) CF 3 Q-1(4-CF 3 ) G-3(3-F) CF 3 Q-1(4-CF 3 ) G-3(3-Cl) CF 3 Q-1(4-CF 3 ) G-3(3-CH 3 ) CF 3 Q-1(4-CF 3 ) G-3(3-CF 3 ) CF 3 Q-1(2-F,4-F) G-1(4-F) CF 3 Q-1(2-F,4-F) G-3(3-F) CF 3 Q-1(2-F,4-F) G-3(3-Cl) CF 3 Q-1(2-F,4-F) G-3(3-CH 3 ) CF 3 Q-1(2-F,4-F) G-3(3-CF 3 ) CF 3Q-1(3-F,4-F) G-1(4-F) CF 3 Q-1(3-F,4-F) G-3(3-F) CF 3 Q-1(3-F,4-F) G-3(3-Cl) CF 3 Q-1(3-F,4-F) G-3(3-CH 3 ) CF 3 Q-1(3-F,4-F) G-3(3-CF 3 ) CF 3 Q-2(4-F) G-1(4-F) CF 3 Q-2(4-F) G-3(3-F) CF 3 Q-2(4-F) G-3(3-Cl) CF 3 Q-2(4-F) G-3(3-CH 3 ) CF 3 Q-2(4-F) G-3(3-CF 3 ) CF 3 Q-3 G-1(4-F) CF 3 Q-3 G-3(3-F) CF 3 Q-3 G-3(3-Cl) CF 3 Q-3 G-3(3-CH 3 ) CF 3 Q-3 G-3(3-CF 3 ) CF 3 Q-3(4-F) G-1(4-F) CF 3 Q-3(4-F) G-3(3-F) CF 3 Q-3(4-F) G-3(3-Cl) CF 3 Q-3(4-F) G-3(3-CH 3 ) CF 3 Q-3(4-F) G-3(3-CF 3 ) CF3 Q-3(4-Cl) G-1(4-F) CF 3 Q-3(4-Cl) G-3(3-F) CF 3 Q-3(4-Cl) G-3(3-Cl) CF 3 Q-3(4-Cl) G-3(3-CH 3 ) CF 3 Q-3(4-Cl) G-3(3-CF 3 ) CF 3 Q-3(4-CH 3 ) G-1(4-F) CF 3 Q-3(4-CH 3 ) G-3(3-F) CF 3 Q-3(4-CH 3 ) G-3(3-Cl) CF 3 Q-3(4-CH 3 ) G-3(3-CH 3 ) CF 3 Q-3(4-CH 3 ) G-3(3-CF 3 ) CF 3 Q-3(3-CH 3 ) G-1(4-F) CF 3 Q-3(3-CH 3 ) G-3(3-F) CF 3 Q-3(3-CH 3 ) G-3(3-Cl) CF 3 Q-3(3-CH 3 ) G-3(3-CH 3 ) CF 3 Q-3(3-CH 3 ) G-3(3-CF 3 ) CF 3 Q-3(3-OCH 3 ) G-1(4-F) CF 3 Q-3(3-OCH 3) G-3(3-F) CF 3 Q-3(3-OCH 3 ) G-3(3-Cl) CF 3 Q-3(3-OCH 3 ) G-3(3-CH 3 ) CF 3 Q-3(3-OCH 3 ) G-3(3-CF 3 ) CF 3 Q-4 G-1(4-F) CF 3 Q-4 G-3(3-F) CF 3 Q-4 G-3(3-Cl) CF 3 Q-4 G-3(3-CH 3 ) CF 3 Q-4 G-3(3-CF 3 ) CF 3 Q-4(4-CH 3 ) G-1(4-F) CF 3 Q-4(4-CH 3 ) G-3(3-F) CF 3 Q-4(4-CH 3 ) G-3(3-Cl) CF 3 Q-4(4-CH 3 ) G-3(3-CH 3 ) CF 3 Q-4(4-CH 3 ) G-3(3-CF 3 ) CF 3 Q-4(3-CH 3 ) G-1(4-F) CF 3 Q-4(3-CH 3 ) G-3(3-F) CF 3 Q-4(3-CH 3 ) G-3(3-Cl) CF 3 Q-4(3-CH 3) G-3(3-CH 3 ) CF 3 Q-4(3-CH 3 ) G-3(3-CF 3 ) CF 3 Q-9 G-1(4-F) CF 3 Q-9 G-3(3-F) CF 3 Q-9 G-3(3-Cl) CF 3 Q-9 G-3(3-CH 3 ) CF 3 Q-9 G-3(3-CF 3 ) CF 3 Q-12a G-1(4-F) CF 3 Q-12a G-3(3-F) CF 3 Q-12a G-3(3-Cl) CF 3 Q-12a G-3(3-CH 3 ) CF 3 Q-12a G-3(3-CF 3 ) CF 3 Q-1(4-F) G-1(4-NO 2 ) CF 3 Q-1(4-F) G-1(4-NH 2 ) CF 3 Q-1(4-F) G-1(5-F) CF 3 Q-1(4-F) G-1(5-NO 2 ) CF 3 Q-1(4-F) G-1(5-NH 2 ) CF 3 Q-1(4-F) G-3(3-NO 2 ) CF 3 Q-1(4-F) G-3(3-NH 2 ) CF 3Q-1(4-CN) G-1(4-NO 2 ) CF 3 Q-1(4-CN) G-1(4-NH 2 ) CF 3 Q-1(4-CN) G-1(5-F) CF 3 Q-1(4-CN) G-1(5-NO 2 ) CF 3 Q-1(4-CN) G-1(5-NH 2 ) CF 3 Q-1(4-CN) G-3(3-NO 2 ) CF 3 Q-1(4-CN) G-3(3-NH 2 ) CF 3 Q-2(4-F) G-1(4-NO 2 ) CF 3 Q-2(4-F) G-1(4-NH 2 ) CF 3 Q-2(4-F) G-1(5-F) CF 3 Q-2(4-F) G-1(5-NO 2 ) CF 3 Q-2(4-F) G-1(5-NH 2 ) CF 3 Q-2(4-F) G-3(3-NO 2 ) CF 3 Q-2(4-F) G-3(3-NH 2 ) CF 3 Q-2(4-Cl) G-1(4-F) CF 3 Q-2(4-Cl) G-1(4-NO 2 ) CF 3 Q-2(4-Cl) G-1(4-NH 2 ) CF 3 Q-2(4-Cl) G-1(5-F) CF 3 Q-2(4-Cl) G-1(5-NO 2 ) CF 3 Q-2(4-Cl) G-1(5-NH 2 ) CF 3 Q-2(4-Cl) G-3(3-F) CF 3 Q-2(4-Cl) G-3(3-Cl) CF 3 Q-2(4-Cl) G-3(3-CH 3 ) CF 3 Q-2(4-Cl) G-3(3-CF 3 ) CF 3 Q-2(4-Cl) G-3(3-NO 2 ) CF 3 Q-2(4-Cl) G-3(3-NH 2 ) CF 3 Q-2(4-CN) G-1(4-F) CF 3 Q-2(4-CN) G-1(4-NO 2 ) CF 3 Q-2(4-CN) G-1(4-NH 2 ) CF 3 Q-2(4-CN) G-1(5-F) CF 3 Q-2(4-CN) G-1(5-NO 2 ) CF 3 Q-2(4-CN) G-1(5-NH 2 ) CF 3 Q-2(4-CN) G-3(3-F) CF 3 Q-2(4-CN) G-3(3-Cl) CF 3 Q-2(4-CN) G-3(3-CH 3 ) CF 3 Q-2(4-CN) G-3(3-CF 3 ) CF3 Q-2(4-CN) G-3(3-NO 2 ) CF 3 Q-2(4-CN) G-3(3-NH 2 ) CF 3 Q-3 G-1(4-NO 2 ) CF 3 Q-3 G-1(4-NH 2 ) CF 3 Q-3 G-1(5-F) CF 3 Q-3 G-1(5-NO 2 ) CF 3 Q-3 G-1(5-NH 2 ) CF 3 Q-3 G-3(3-NO 2 ) CF 3 Q-3 G-3(3-NH 2 ) CF 3 Q-3(3-CH 3 ) G-1(4-NO 2 ) CF 3 Q-3(3-CH 3 ) G-1(4-NH 2 ) CF 3 Q-3(3-CH 3 ) G-1(5-F) CF 3 Q-3(3-CH 3 ) G-1(5-NO 2 ) CF 3 Q-3(3-CH 3 ) G-1(5-NH 2 ) CF 3 Q-3(3-CH 3 ) G-3(3-NO 2 ) CF 3 Q-3(3-CH 3 ) G-3(3-NH 2 ) CF 3Q-3(3-Cl) G-1(4-F) CF 3 Q-3(3-Cl) G-1(4-NO 2 ) CF 3 Q-3(3-Cl) G-1(4-NH 2 ) CF 3 Q-3(3-Cl) G-1(5-F) CF 3 Q-3(3-Cl) G-1(5-NO 2 ) CF 3 Q-3(3-Cl) G-1(5-NH 2 ) CF 3 Q-3(3-Cl) G-3(3-F) CF 3 Q-3(3-Cl) G-3(3-Cl) CF 3 Q-3(3-Cl) G-3(3-CH 3 ) CF 3 Q-3(3-Cl) G-3(3-CF 3 ) CF 3 Q-3(3-Cl) G-3(3-NO 2 ) CF 3 Q-3(3-Cl) G-3(3-NH 2 ) CF 3 Q-3(3-F) G-1(4-F) CF 3 Q-3(3-F) G-1(4-NO 2 ) CF 3 Q-3(3-F) G-1(4-NH 2 ) CF 3 Q-3(3-F) G-1(5-F) CF 3 Q-3(3-F) G-1(5-NO 2 ) CF 3 Q-3(3-F) G-1(5-NH 2 ) CF 3Q-3(3-F) G-3(3-F) CF 3 Q-3(3-F) G-3(3-Cl) CF 3 Q-3(3-F) G-3(3-CH 3 ) CF 3 Q-3(3-F) G-3(3-CF 3 ) CF 3 Q-3(3-F) G-3(3-NO 2 ) CF 3 Q-3(3-F) G-3(3-NH 2 ) CF 3 Q-3(4-Br) G-1(4-F) CF 3 Q-3(4-Br) G-1(4-NO 2 ) CF 3 Q-3(4-Br) G-1(4-NH 2 ) CF 3 Q-3(4-Br) G-1(5-F) CF 3 Q-3(4-Br) G-1(5-NO 2 ) CF 3 Q-3(4-Br) G-1(5-NH 2 ) CF 3 Q-3(4-Br) G-3(3-F) CF 3 Q-3(4-Br) G-3(3-Cl) CF 3 Q-3(4-Br) G-3(3-CH 3 ) CF 3 Q-3(4-Br) G-3(3-CF 3 ) CF 3 Q-3(4-Br) G-3(3-NO 2 ) CF 3 Q-3(4-Br) G-3(3-NH 2 ) CF 3 Q-3(4-CH3 ) G-1(4-NO 2 ) CF 3 Q-3(4-CH 3 ) G-1(4-NH 2 ) CF 3 Q-3(4-CH 3 ) G-1(5-F) CF 3 Q-3(4-CH 3 ) G-1(5-NO 2 ) CF 3 Q-3(4-CH 3 ) G-1(5-NH 2 ) CF 3 Q-3(4-CH 3 ) G-3(3-NO 2 ) CF 3 Q-3(4-CH 3 ) G-3(3-NH 2 ) CF 3 Q-3(4-Cl) G-1(4-NO 2 ) CF 3 Q-3(4-Cl) G-1(4-NH 2 ) CF 3 Q-3(4-Cl) G-1(5-F) CF 3 Q-3(4-Cl) G-1(5-NO 2 ) CF 3 Q-3(4-Cl) G-1(5-NH 2 ) CF 3 Q-3(4-Cl) G-3(3-NO 2 ) CF 3 Q-3(4-Cl) G-3(3-NH 2 ) CF 3 Q-3(4-CN) G-1(4-F) CF 3 Q-3(4-CN) G-1(4-NO 2 ) CF 3Q-3(4-CN) G-1(4-NH 2 ) CF 3 Q-3(4-CN) G-1(5-F) CF 3 Q-3(4-CN) G-1(5-NO 2 ) CF 3 Q-3(4-CN) G-1(5-NH 2 ) CF 3 Q-3(4-CN) G-3(3-F) CF 3 Q-3(4-CN) G-3(3-Cl) CF 3 Q-3(4-CN) G-3(3-CH 3 ) CF 3 Q-3(4-CN) G-3(3-CF 3 ) CF 3 Q-3(4-CN) G-3(3-NO 2 ) CF 3 Q-3(4-CN) G-3(3-NH 2 ) CF 3 Q-3(4-F) G-1(4-NO 2 ) CF 3 Q-3(4-F) G-1(4-NH 2 ) CF 3 Q-3(4-F) G-1(5-F) CF 3 Q-3(4-F) G-1(5-NO 2 ) CF 3 Q-3(4-F) G-1(5-NH 2 ) CF 3 Q-3(4-F) G-3(3-NO 2 ) CF 3 Q-3(4-F) G-3(3-NH 2 ) CF 3 Q-3(6-F) G-1(4-F) CF 3Q-3(6-F) G-1(4-NO 2 ) CF 3 Q-3(6-F) G-1(4-NH 2 ) CF 3 Q-3(6-F) G-1(5-F) CF 3 Q-3(6-F) G-1(5-NO 2 ) CF 3 Q-3(6-F) G-1(5-NH 2 ) CF 3 Q-3(6-F) G-3(3-F) CF 3 Q-3(6-F) G-3(3-Cl) CF 3 Q-3(6-F) G-3(3-CH 3 ) CF 3 Q-3(6-F) G-3(3-CF 3 ) CF 3 Q-3(6-F) G-3(3-NO 2 ) CF 3 Q-3(6-F) G-3(3-NH 2 ) CF 3 Q-4 G-1(4-NO 2 ) CF 3 Q-4 G-1(4-NH 2 ) CF 3 Q-4 G-1(5-F) CF 3 Q-4 G-1(5-NO 2 ) CF 3 Q-4 G-1(5-NH 2 ) CF 3 Q-4 G-3(3-NO 2 ) CF 3 Q-4 G-3(3-NH 2 ) CF 3 Q-4(3-CH 3) G-1(4-NO 2 ) CF 3 Q-4(3-CH 3 ) G-1(4-NH 2 ) CF 3 Q-4(3-CH 3 ) G-1(5-F) CF 3 Q-4(3-CH 3 ) G-1(5-NO 2 ) CF 3 Q-4(3-CH 3 ) G-1(5-NH 2 ) CF 3 Q-4(3-CH 3 ) G-3(3-NO 2 ) CF 3 Q-4(3-CH 3 ) G-3(3-NH 2 ) CF 3 Q-4(3-Cl) G-1(4-F) CF 3 Q-4(3-Cl) G-1(4-NO 2 ) CF 3 Q-4(3-Cl) G-1(4-NH 2 ) CF 3 Q-4(3-Cl) G-1(5-F) CF 3 Q-4(3-Cl) G-1(5-NO 2 ) CF 3 Q-4(3-Cl) G-1(5-NH 2 ) CF 3 Q-4(3-Cl) G-3(3-F) CF 3 Q-4(3-Cl) G-3(3-Cl) CF 3 Q-4(3-Cl) G-3(3-CH 3 ) CF 3 Q-4(3-Cl) G-3(3-CF 3 ) CF 3 Q-4(3-Cl) G-3(3-NO 2 ) CF 3 Q-4(3-Cl) G-3(3-NH 2 ) CF 3 Q-4(4-Br) G-1(4-F) CF 3 Q-4(4-Br) G-1(4-NO 2 ) CF 3 Q-4(4-Br) G-1(4-NH 2 ) CF 3 Q-4(4-Br) G-1(5-F) CF 3 Q-4(4-Br) G-1(5-NO 2 ) CF 3 Q-4(4-Br) G-1(5-NH 2 ) CF 3 Q-4(4-Br) G-3(3-F) CF 3 Q-4(4-Br) G-3(3-Cl) CF 3 Q-4(4-Br) G-3(3-CH 3 ) CF 3 Q-4(4-Br) G-3(3-CF 3 ) CF 3 Q-4(4-Br) G-3(3-NO 2 ) CF 3 Q-4(4-Br) G-3(3-NH 2 ) CF 3 Q-4(4-Cl) G-1(4-F) CF 3 Q-4(4-Cl) G-1(4-NO 2 ) CF 3 Q-4(4-Cl) G-1(4-NH 2 ) CF 3 Q-4(4-Cl) G-1(5-F) CF 3 Q-4(4-Cl) G-1(5-NO 2 ) CF 3 Q-4(4-Cl) G-1(5-NH 2 ) CF 3 Q-4(4-Cl) G-3(3-F) CF 3 Q-4(4-Cl) G-3(3-Cl) CF 3 Q-4(4-Cl) G-3(3-CH 3 ) CF 3 Q-4(4-Cl) G-3(3-CF 3 ) CF 3 Q-4(4-Cl) G-3(3-NO 2 ) CF 3 Q-4(4-Cl) G-3(3-NH 2 ) CF 3 Q-9 G-1(4-NO 2 ) CF 3 Q-9 G-1(4-NH 2 ) CF 3 Q-9 G-1(5-F) CF 3 Q-9 G-1(5-NO 2 ) CF 3 Q-9 G-1(5-NH 2 ) CF 3 Q-9 G-3(3-NO 2 ) CF 3 Q-9 G-3(3-NH 2 ) CF 3 Q-12a G-1(4-NO 2 ) CF 3 Q-12a G-1(4-NH 2 ) CF 3 Q-12a G-1(5-F) CF 3Q-12a G-1(5-NO 2 ) CF 3 Q-12a G-1(5-NH 2 ) CF 3 Q-12a G-3(3-NO 2 ) CF 3 Q-12a G-3(3-NH 2 ) Cl Q-1(4-F) G-1(4-F) Cl Q-1(4-F) G-1(4-NO 2 ) Cl Q-1(4-F) G-1(4-NH 2 ) Cl Q-1(4-F) G-1(5-F) Cl Q-1(4-F) G-1(5-NO 2 ) Cl Q-1(4-F) G-1(5-NH 2 ) Cl Q-1(4-F) G-3(3-F) Cl Q-1(4-F) G-3(3-Cl) Cl Q-1(4-F) G-3(3-CH 3 ) Cl Q-1(4-F) G-3(3-CF 3 ) Cl Q-1(4-F) G-3(3-NO 2 ) Cl Q-1(4-F) G-3(3-NH 2 ) Cl Q-1(4-CN) G-1(4-F) Cl Q-1(4-CN) G-1(4-NO 2 ) Cl Q-1(4-CN) G-1(4-NH 2 ) Cl Q-1(4-CN) G-1(5-F) Cl Q-1(4-CN) G-1(5-NO 2 ) Cl Q-1(4-CN) G-1(5-NH 2 ) Cl Q-1(4-CN) G-3(3-F) Cl Q-1(4-CN) G-3(3-Cl) Cl Q-1(4-CN) G-3(3-CH 3 ) Cl Q-1(4-CN) G-3(3-CF 3 ) Cl Q-1(4-CN) G-3(3-NO 2 ) Cl Q-1(4-CN) G-3(3-NH 2 ) Cl Q-2(4-F) G-1(4-F) Cl Q-2(4-F) G-1(4-NO 2 ) Cl Q-2(4-F) G-1(4-NH 2 ) Cl Q-2(4-F) G-1(5-F) Cl Q-2(4-F) G-1(5-NO 2 ) Cl Q-2(4-F) G-1(5-NH 2 ) Cl Q-2(4-F) G-3(3-F) Cl Q-2(4-F) G-3(3-Cl) Cl Q-2(4-F) G-3(3-CH 3 ) Cl Q-2(4-F) G-3(3-CF 3 ) Cl Q-2(4-F) G-3(3-NO 2 ) Cl Q-2(4-F) G-3(3-NH 2 ) Cl Q-2(4-Cl) G-1(4-F) Cl Q-2(4-Cl) G-1(4-NO 2 ) Cl Q-2(4-Cl) G-1(4-NH 2 ) Cl Q-2(4-Cl) G-1(5-F) Cl Q-2(4-Cl) G-1(5-NO 2 ) Cl Q-2(4-Cl) G-1(5-NH 2 ) Cl Q-2(4-Cl) G-3(3-F) Cl Q-2(4-Cl) G-3(3-Cl) Cl Q-2(4-Cl) G-3(3-CH 3 ) Cl Q-2(4-Cl) G-3(3-CF 3 ) Cl Q-2(4-Cl) G-3(3-NO 2 ) Cl Q-2(4-Cl) G-3(3-NH 2 ) Cl Q-2(4-CN) G-1(4-F) Cl Q-2(4-CN) G-1(4-NO 2 ) Cl Q-2(4-CN) G-1(4-NH 2 ) Cl Q-2(4-CN) G-1(5-F) Cl Q-2(4-CN) G-1(5-NO 2 ) Cl Q-2(4-CN) G-1(5-NH 2 ) Cl Q-2(4-CN) G-3(3-F) Cl Q-2(4-CN) G-3(3-Cl) Cl Q-2(4-CN) G-3(3-CH 3 ) Cl Q-2(4-CN) G-3(3-CF 3 ) Cl Q-2(4-CN) G-3(3-NO 2 ) Cl Q-2(4-CN) G-3(3-NH 2 ) Cl Q-3 G-1(4-F) Cl Q-3 G-1(4-NO 2 ) Cl Q-3 G-1(4-NH 2 ) Cl Q-3 G-1(5-F) Cl Q-3 G-1(5-NO 2 ) Cl Q-3 G-1(5-NH 2) Cl Q-3 G-3(3-F) Cl Q-3 G-3(3-Cl) Cl Q-3 G-3(3-CH 3 ) Cl Q-3 G-3(3-CF 3 ) Cl Q-3 G-3(3-NO 2 ) Cl Q-3 G-3(3-NH 2 ) Cl Q-3(3-CH 3 ) G-1(4-F) Cl Q-3(3-CH 3 ) G-1(4-NO 2 ) Cl Q-3(3-CH 3 ) G-1(4-NH 2 ) Cl Q-3(3-CH 3 ) G-1(5-F) Cl Q-3(3-CH 3 ) G-1(5-NO 2 ) Cl Q-3(3-CH 3 ) G-1(5-NH 2 ) Cl Q-3(3-CH 3 ) G-3(3-F) Cl Q-3(3-CH 3 ) G-3(3-Cl) Cl Q-3(3-CH 3 ) G-3(3-CH 3 ) Cl Q-3(3-CH 3 ) G-3(3-CF 3 ) Cl Q-3(3-CH 3 ) G-3(3-NO 2 ) Cl Q-3(3-CH 3 ) G-3(3-NH 2 ) Cl Q-3(3-Cl) G-1(4-F) Cl Q-3(3-Cl) G-1(4-NO 2 ) Cl Q-3(3-Cl) G-1(4-NH 2 ) Cl Q-3(3-Cl) G-1(5-F) Cl Q-3(3-Cl) G-1(5-NO 2 ) Cl Q-3(3-Cl) G-1(5-NH 2 ) Cl Q-3(3-Cl) G-3(3-F) Cl Q-3(3-Cl) G-3(3-Cl) Cl Q-3(3-Cl) G-3(3-CH 3 ) Cl Q-3(3-Cl) G-3(3-CF 3 ) Cl Q-3(3-Cl) G-3(3-NO 2 ) Cl Q-3(3-Cl) G-3(3-NH 2 ) Cl Q-3(3-F) G-1(4-F) Cl Q-3(3-F) G-1(4-NO 2 ) Cl Q-3(3-F) G-1(4-NH 2 ) Cl Q-3(3-F) G-1(5-F) Cl Q-3(3-F) G-1(5-NO 2 ) Cl Q-3(3-F) G-1(5-NH 2 ) Cl Q-3(3-F) G-3(3-F) Cl Q-3(3-F) G-3(3-Cl) Cl Q-3(3-F) G-3(3-CH 3 ) Cl Q-3(3-F) G-3(3-CF 3 ) Cl Q-3(3-F) G-3(3-NO 2 ) Cl Q-3(3-F) G-3(3-NH 2 ) Cl Q-3(4-Br) G-1(4-F) Cl Q-3(4-Br) G-1(4-NO 2 ) Cl Q-3(4-Br) G-1(4-NH 2 ) Cl Q-3(4-Br) G-1(5-F) Cl Q-3(4-Br) G-1(5-NO 2 ) Cl Q-3(4-Br) G-1(5-NH 2 ) Cl Q-3(4-Br) G-3(3-F) Cl Q-3(4-Br) G-3(3-Cl) Cl Q-3(4-Br) G-3(3-CH 3 ) Cl Q-3(4-Br) G-3(3-CF 3 ) Cl Q-3(4-Br) G-3(3-NO 2 ) Cl Q-3(4-Br) G-3(3-NH 2 ) Cl Q-3(4-CH 3 ) G-1(4-F) Cl Q-3(4-CH 3 ) G-1(4-NO 2 ) Cl Q-3(4-CH 3 ) G-1(4-NH 2 ) Cl Q-3(4-CH 3 ) G-1(5-F) Cl Q-3(4-CH 3 ) G-1(5-NO 2 ) Cl Q-3(4-CH 3 ) G-1(5-NH 2 ) Cl Q-3(4-CH 3 ) G-3(3-F) Cl Q-3(4-CH 3 ) G-3(3-Cl) Cl Q-3(4-CH 3 ) G-3(3-CH 3 ) Cl Q-3(4-CH3 ) G-3(3-CF 3 ) Cl Q-3(4-CH 3 ) G-3(3-NO 2 ) Cl Q-3(4-CH 3 ) G-3(3-NH 2 ) Cl Q-3(4-Cl) G-1(4-F) Cl Q-3(4-Cl) G-1(4-NO 2 ) Cl Q-3(4-Cl) G-1(4-NH 2 ) Cl Q-3(4-Cl) G-1(5-F) Cl Q-3(4-Cl) G-1(5-NO 2 ) Cl Q-3(4-Cl) G-1(5-NH 2 ) Cl Q-3(4-Cl) G-3(3-F) Cl Q-3(4-Cl) G-3(3-Cl) Cl Q-3(4-Cl) G-3(3-CH 3 ) Cl Q-3(4-Cl) G-3(3-CF 3 ) Cl Q-3(4-Cl) G-3(3-NO 2 ) Cl Q-3(4-Cl) G-3(3-NH 2 ) Cl Q-3(4-CN) G-1(4-F) Cl Q-3(4-CN) G-1(4-NO 2 ) Cl Q-3(4-CN) G-1(4-NH 2 ) Cl Q-3(4-CN) G-1(5-F) Cl Q-3(4-CN) G-1(5-NO 2 ) Cl Q-3(4-CN) G-1(5-NH 2 ) Cl Q-3(4-CN) G-3(3-F) Cl Q-3(4-CN) G-3(3-Cl) Cl Q-3(4-CN) G-3(3-CH 3 ) Cl Q-3(4-CN) G-3(3-CF 3 ) Cl Q-3(4-CN) G-3(3-NO 2 ) Cl Q-3(4-CN) G-3(3-NH 2 ) Cl Q-3(4-F) G-1(4-F) Cl Q-3(4-F) G-1(4-NO 2 ) Cl Q-3(4-F) G-1(4-NH 2 ) Cl Q-3(4-F) G-1(5-F) Cl Q-3(4-F) G-1(5-NO 2 ) Cl Q-3(4-F) G-1(5-NH 2 ) Cl Q-3(4-F) G-3(3-F) Cl Q-3(4-F) G-3(3-Cl) Cl Q-3(4-F) G-3(3-CH 3 ) Cl Q-3(4-F) G-3(3-CF 3 ) Cl Q-3(4-F) G-3(3-NO 2 ) Cl Q-3(4-F) G-3(3-NH 2 ) Cl Q-3(6-F) G-1(4-F) Cl Q-3(6-F) G-1(4-NO 2 ) Cl Q-3(6-F) G-1(4-NH 2 ) Cl Q-3(6-F) G-1(5-F) Cl Q-3(6-F) G-1(5-NO 2 ) Cl Q-3(6-F) G-1(5-NH 2 ) Cl Q-3(6-F) G-3(3-F) Cl Q-3(6-F) G-3(3-Cl) Cl Q-3(6-F) G-3(3-CH 3 ) Cl Q-3(6-F) G-3(3-CF 3 ) Cl Q-3(6-F) G-3(3-NO 2 ) Cl Q-3(6-F) G-3(3-NH 2 ) Cl Q-4 G-1(4-F) Cl Q-4 G-1(4-NO 2 ) Cl Q-4 G-1(4-NH 2 ) Cl Q-4 G-1(5-F) Cl Q-4 G-1(5-NO 2 ) Cl Q-4 G-1(5-NH 2 ) Cl Q-4 G-3(3-F) Cl Q-4 G-3(3-Cl) Cl Q-4 G-3(3-CH 3 ) Cl Q-4 G-3(3-CF 3 ) Cl Q-4 G-3(3-NO 2 ) Cl Q-4 G-3(3-NH 2 ) Cl Q-4(3-CH 3 ) G-1(4-F) Cl Q-4(3-CH 3 ) G-1(4-NO 2 ) Cl Q-4(3-CH 3 ) G-1(4-NH 2 ) Cl Q-4(3-CH 3 ) G-1(5-F) Cl Q-4(3-CH 3 ) G-1(5-NO 2 ) Cl Q-4(3-CH3 ) G-1(5-NH 2 ) Cl Q-4(3-CH 3 ) G-3(3-F) Cl Q-4(3-CH 3 ) G-3(3-Cl) Cl Q-4(3-CH 3 ) G-3(3-CH 3 ) Cl Q-4(3-CH 3 ) G-3(3-CF 3 ) Cl Q-4(3-CH 3 ) G-3(3-NO 2 ) Cl Q-4(3-CH 3 ) G-3(3-NH 2 ) Cl Q-4(3-Cl) G-1(4-F) Cl Q-4(3-Cl) G-1(4-NO 2 ) Cl Q-4(3-Cl) G-1(4-NH 2 ) Cl Q-4(3-Cl) G-1(5-F) Cl Q-4(3-Cl) G-1(5-NO 2 ) Cl Q-4(3-Cl) G-1(5-NH 2 ) Cl Q-4(3-Cl) G-3(3-F) Cl Q-4(3-Cl) G-3(3-Cl) Cl Q-4(3-Cl) G-3(3-CH 3 ) Cl Q-4(3-Cl) G-3(3-CF 3 ) Cl Q-4(3-Cl) G-3(3-NO 2 ) Cl Q-4(3-Cl) G-3(3-NH 2 ) Cl Q-4(4-Br) G-1(4-F) Cl Q-4(4-Br) G-1(4-NO 2 ) Cl Q-4(4-Br) G-1(4-NH 2 ) Cl Q-4(4-Br) G-1(5-F) Cl Q-4(4-Br) G-1(5-NO 2 ) Cl Q-4(4-Br) G-1(5-NH 2 ) Cl Q-4(4-Br) G-3(3-F) Cl Q-4(4-Br) G-3(3-Cl) Cl Q-4(4-Br) G-3(3-CH 3 ) Cl Q-4(4-Br) G-3(3-CF 3 ) Cl Q-4(4-Br) G-3(3-NO 2 ) Cl Q-4(4-Br) G-3(3-NH 2 ) Cl Q-4(4-Cl) G-1(4-F) Cl Q-4(4-Cl) G-1(4-NO 2 ) Cl Q-4(4-Cl) G-1(4-NH 2 ) Cl Q-4(4-Cl) G-1(5-F) Cl Q-4(4-Cl) G-1(5-NO 2 ) Cl Q-4(4-Cl) G-1(5-NH 2 ) Cl Q-4(4-Cl) G-3(3-F) Cl Q-4(4-Cl) G-3(3-Cl) Cl Q-4(4-Cl) G-3(3-CH 3 ) Cl Q-4(4-Cl) G-3(3-CF 3 ) Cl Q-4(4-Cl) G-3(3-NO 2 ) Cl Q-4(4-Cl) G-3(3-NH 2 ) Cl Q-9 G-1(4-F) Cl Q-9 G-1(4-NO 2 ) Cl Q-9 G-1(4-NH 2 ) Cl Q-9 G-1(5-F) Cl Q-9 G-1(5-NO 2 ) Cl Q-9 G-1(5-NH 2 ) Cl Q-9 G-3(3-F) Cl Q-9 G-3(3-Cl) Cl Q-9 G-3(3-CH 3 ) Cl Q-9 G-3(3-CF 3 ) Cl Q-9 G-3(3-NO 2 ) Cl Q-9 G-3(3-NH 2 ) Cl Q-12a G-1(4-F) Cl Q-12a G-1(4-NO 2 ) Cl Q-12a G-1(4-NH 2 ) Cl Q-12a G-1(5-F) Cl Q-12a G-1(5-NO 2 ) Cl Q-12a G-1(5-NH 2 ) Cl Q-12a G-3(3-F) Cl Q-12a G-3(3-Cl) Cl Q-12a G-3(3-CH 3 ) Cl Q-12a G-3(3-CF 3 ) Cl Q-12a G-3(3-NO 2 ) Cl Q-12a G-3(3-NH 2 ) ――――――――――――――――

[0085] The pest control agent in the present invention means a pest control agent targeting harmful arthropods in the fields of agriculture, horticulture, livestock, and hygiene (internal and external parasites for mammals or birds as livestock and pets, and household and commercial hygiene pests and nuisance pests).

[0086] Also, the agricultural chemical in the present invention means insecticides, acaricides, nematicides, herbicides, fungicides, etc. in the fields of agriculture and horticulture.

[0087] The hygiene pests in this specification refer to harmful invertebrates that cause allergic symptoms such as severe pain, swelling, and itching by biting the target animal, and in some cases, cause fatal anaphylactic shock, and sometimes transmit serious diseases during blood-sucking and may even cause death; invertebrates that contaminate with pathogens such as viruses, bacteria, and parasites when contacting food; invertebrates whose living bodies, corpses, molted shells, feces, etc. become allergens and cause allergic diseases such as bronchial asthma, rhinitis, conjunctivitis, and atopic dermatitis; invertebrates that cause economic damage by damaging food, clothing, houses, etc.; and invertebrates that do not directly cause harm but cause discomfort by occurring and invading human living environments. More specifically, it means ants that bite with large jaws, wasps that sting with poison stings, mosquitoes and turtles that suck blood from the skin, and termites that are omnivorous and damage buildings such as houses.

[0088] The nuisance pests in this specification refer to pests that do not directly harm humans in the human living environment but cause discomfort and psychological harm due to their appearance and shape.

[0089] Specific examples of insects, mites, crustaceans, mollusks, nematodes, external parasites, and internal parasites that can be controlled using the compound of the present invention include, for example, the following organisms, but the present invention is not limited thereto.

[0090] As pests, Lepidoptera; Allium leafminer (Acrolepiopsis sapporensis), Yam leafminer (Acrolepiopsis suzukiella), Smaller tea tortrix (Adoxophyes honmai), Summer fruit tortrix (Adoxophyes orana fasciata), Fruit-piercing moth (Adris tyrannus), Sweet potato leaf worm (Aedia leucomelas), Black cutworm (Agrotis ipsilon), Turnip moth (Agrotis segetum), cotton leafworm (Alabama argillacea), Asiatic leafroller (Archips breviplicanus), Apple tortrix (Archips fuscocupreanus), Oriental tussock moth (Artaxa subflava), Bamboo zygaenid (Artona martini), Japanese giant looper (Ascotis selenaria), Asiatic common looper (Autographa nigrisigna), Pear leaf miner (Bucculatrix pyrivorella), Tea leafroller (Caloptilia theivora), Peach fruit moth (Carposina sasakii), Rice stem borer (Chilo suppressalis), Rice leafroller (Cnaphalocrocis medinalis), Yellow peach moth (Conogethespunctiferalis), Carpenter moth (Cossus insularis), Threespotted plusia (Ctenoplusia agnata), Codling moth (Cydia pomonella), Pine moth (Dendrolimus spectabilis), Japanese hemlock caterpillar (Dendrolimus superans), Cucumber moth (Diaphania indica), sugarcane borer (Diatraea saccharalis), Eilema fuscodorsalis (Eilema fuscodorsalis), Eilema laevis (Eilema laevis), Lesser corn stalk borer (Elasmopalpus lignosellus), Grape berry moth (Endopiza viteana), Limabean pod borer (Etiella zinckenella), Euproctis piperita (Euproctis piperita), Tea tussock moth (Euproctis pseudoconspersa), Japanese bamboo lappet moth (Euthrix albomaculata), Drinker moth (Euthrix potatoria), Oriental lappet (Gastropacha orientalis), Mulberry pyralid (Glyphodes pyloalis), Plum fruit moth (Grapholita dimorpha), Oriental fruit moth (Grapholita molesta), Sweetpotato leaffolder (Helcystogramma triannulella), Cottonbollworm (Helicoverpa armigera), Oriental tobacco budworm (Helicoverpa assulta), Corn earworm (Helicoverpa zea), Tobacco budworm (Heliothis virescens), Cabbage webworm (Hellula undalis), Oriental tea tortrix (Homona magnanima), Fall webworm moth (Hyphantria cunea), Pearleaf worm (Illiberis pruni), Prunus bud moth (Illiberis rotundata), Quercus lasiocampid (Kunugia undans), Quercus lasiocampid (Kunugia yamadai), Soybean pod borer (Leguminivora glycinivorella), Mulberry tiger moth (Lemyra imparilis), Gypsy moth (Lymantria dispar), Peach leafminer (Lyonetia clerkella), Lyonetia prunifoliella malinella (Lyonetia prunifoliella malinella), Cabbage armyworm (Mamestra brassicae), Tomato hornworm (Manduca quinquemaculata), Tobacco hornworm (Manduca sexta), Soybean podworm (Matsumuraeses phaseoli), Oriental moth (Monema flavescens), Rice green caterpillar (Narangaaenescens), White-spotted tussock moth (Orgyia thyellina), Asian corn borer (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), Adzuki bean borer (Ostrinia scapulalis), Dark fruit-tree tortrix (Pandemis heparana), Bluegrass webworm (Parapediasia teterrella), Green cochlid (Parasa consocia), Parasa lepida (Parasa lepida), Chinese cochlid (Parasa sinica), Straight swift (Parnara guttata), Pink bollworm (Pectinophora gossypiella), Citrus leafminer (Phyllocnistis citrella), Apple leafminer (Phyllonorycter ringoniella), Large white (Pieris brassicae), Cabbage white butterfly (Pieris rapae crucivora), Diamondback moth (Plutella xylostella), Oriental armyworm (Pseudaletia separata), Soybean looper (Pseudoplusia includens), Swan moth (Sphrageidus similis), Lawn grass cutworm (Spodoptera depravata), Southern armyworm (Spodoptera eridania), Beet armyworm (Spodopteraexigua), Fall armyworm (Spodoptera frugiperda), Cotton leafworm (Spodoptera littoralis), Common cutworm (Spodoptera litura), Persimmon fruit moth (Stathmopoda masinissa), Peach tree borer (Synanthedon exitiosa), Cherry tree borer (Synanthedon hector), Toleria romanovi (Toleria romanovi), Cabbage looper (Trichoplusia ni), etc. Order Coleoptera; Common bean weevil (Acanthoscelides obtectus), Cupreous chafer (Anomala cuprea), Soybean beetle (Anomala rufocuprea), Asian long-horn beetle (Anoplophora glabripennis), White-spotted longicorn beetle (Anoplophora malasiaca), Boll weevil (Anthonomus grandis), Cucurbit leaf beetle (Aulacophora femoralis), Adzuki bean beetle (Callosobruchus chinensis), Beet flea beetle (Chaetocnema concinna), Sweetpotato weevil (Cylas formicarius), Reaf beetle (Demotina fasciculata), Northern corn rootworm (Diabrotica barberi), Southern corn rootworm (Diabrotica undecimpunctata), Western corn rootworm (Diabrotica virgifera), Rice plant weevil (Echinocnemus squameus), Mexican been beetle (Epilachna varivestis), Large twenty-eight-spotted ladybird (Epilachna vigintioctomaculata), Twentyeight-spotted ladybird (Epilachna vigintioctopunctata), Epuraeadomina (Epuraea domina), West Indian sweet potato weevil (Euscepes postfasciatus), Citrus flower chafer (Gametis jucunda), White-fringed beetle (Graphognatus leucoloma), Yellowish elongate chafer (Heptophylla picea), Alfalfa weevil (Hypera postica), Tobacco beetle (Lasioderma serricorne), Colorado potato beetle (Leptinotarsa decemlineata), Rice water weevil (Lissohoptrus oryzophilus), Sweetpotato wireworm (Melanotus fortnumi), Sugarcane wireworm (Melanotus tamsuyensis), Pollen beetle (Meligethes aeneus), Japanese pine sawyer (Monochamus alternatus), Black vine weevil (Otiorhynchus sulcatus), Rice leaf beetle (Oulema oryzae), Rove beetle (Paederus fuscipes), Mustard leaf beetle (Phaedon cochleariae), Striped flea beetle (Phyllotreta striolata), Japanese beetle (Popillia japonica), Yellow-spotted longicorn beetle (Psacothea hilaris), Solanum fleabeetle (Psylliodes angusticollis), Peach curculio (Rhynchites heros), Granary weevil (Sitophilus granarius), Maize weevil (Sitophilus zeamais), Hunting billbug (Sphenophorus venatus vestitus), Yellow mealworm (Tenebrio molitor), Red flour beetle (Tribolium castaneum), Grape borer (Xylotrechus pyrrhoderus), etc. Order Hymenoptera; Chestnut sawfly (Apethymus kuri), Large rose sawfly (Arge pagana), Cabbage sawfly (Athalia infumata), Turnip sawfly (Athalia rosae), Japanese carpenter ant (Camponotus japonicus), Chestnut gall wasp (Dryocosmus kuriphilus), Army ant (Eciton burchellii, E. schmitti), Argentine ant (Linepithema humile), Pharaoh ant (Monomorium pharaonis), Bulldog ant (Myrmecia spp.), European pine sawfly (Neodiprion sertifer), Fire ant (Solenopsis spp.), Asian giant hornet (Vespa mandarinia), Japanese yellow hornet (Vespa simillima), etc. Diptera; Yellow fever mosquito (Aedes aegypti), Asian tiger mosquito (Aedes albopictus), Aedes spp., Aedes taeniorhynchus, Rice leaf miner (Agromyza oryzae), Mexican fruit fly (Anastrepha ludens), African malaria mosquito (Anopheles gambiae), Anopheles hyrcanus sinensis, Anopheles koreicus, Anopheles lesteri, Anopheles maculipennis, Anopheles spp., Soybean pod gall midge (Asphondylia yushimai), Atylotus spp., Melon fly (Bactrocera cucurbitae), Oriental fruit fly (Bactrocera dorsalis), Queensland fruit fly (Bactrocera tryoni), Japanese orange fly (Bactrocera tsuneonis), Boophthora erythrocephala, Braula coeca, Braula spp., Calliphora erythrocephala, Calliphora lata, Calliphora spp.) Blow fly (Calliphora vicina), Mediterranean fruit fly (Ceratitis capitata), Pea leaf miner (Chromatomyia horticola), Old World screw - worm fly (Chrysomya bezziana), Blow fly (Chrysomya chloropyga), Oriental latrine fly (Chrysomya megacephala), Chrysomya spp., Splayed deerfly (Chrysops caecutiens), Chrysops relictus, Chrysops spp., Deer fly (Chrysops suavis), Chrysozona pluvialis, New World screw - worm fly (Cochliomyia hominivorax), House mosquito (Culex pipiens molestus), House mosquito (Culex pipiens pallens), Culex quinquefasciatus, Culex tarsalis, Culex tritaeniorhynchus (Culex tritaeniorhynchus), Culex spp., Biting midge (Culicoides arakawae), Culicoides spp., Bot flies (Cuterebra spp.)、Onion fly (Delia antiqua), Seed corn maggot (Delia platura), Human botfly (Dermatobia hominis), Japanese fruit fly (Drosophila suzukii), Eusimulium spp., Lesser house fly (Fannia canicularis), Fannia spp., Horse nose bot fly (Gasterophilus haemorrhoidalis), Gasterophilus inermis, Horse bot fly (Gasterophilus intestinalis), Throat bot fly (Gasterophilus nasalis), Gasterophilus nigricornis, Gasterophilus pecorum, Gasterophilus spp., Tsetse fly (Glossina morsitans, G. palpalis), Glossina spp., Horn fly (Haematobia irritans), Haematobia irritans exigua, Haematobia spp., Haematobia stimulans, Haematopota italic, Common horse fly (Haematopota pluvialis), Haematopota spp., Forest fly (Hippobosca equina), Hippobosca spp.)、Hippobosca variegate, Hybomitra ciurea, Hybomitra spp., Smaller rice leaf miner (Hydrellia griseola), Hydrotaea albipuncta, Sheep headfly (Hydrotaea irritans), Hydrotaea spp., Warble fly (Hypoderma bovis), Common cattle grub (Hypoderma lineatum), Hypoderma spp., Black gnat (Leptoconops nipponensis), Lipoptena capreoli, Lipoptena cervi, Lipoptena spp., Cabbage leafminer (Liriomyza brassicae), Tomato leaf miner (Liriomyza bryoniae), Stone leek leafminer (Liriomyza chinensis), Pea leafminer (Liriomyza huidobrensis), Tomato leafminer (Liriomyza sativae), Serpentine leafminer (Liriomyza trifolii), Australian sheep blowfly (Lucilia cuprina), Green bottle fly (Lucilia illustris), Common green bottle fly (Lucilia sericata), Lucilia spp., Lutzomyia spp.) Hessian fly (Mayetiola destructor), Sheep ked (Melophagus ovinus), Melophagus spp., Sweat fly (Morellia simplex), Morellia spp., Face fly (Musca autumnalis), Housefly (Musca domestica), Musca spp., Australian bush fly (Musca vetustissima), Odagmia ornata, Odagmia spp., Sheep nasal bot fly (Oestrus ovis), Oestrus spp., Beet leaf miner (Pegomya cunicularia), Philipomyia spp., Phlebotomus longipalpis, Phlebotomus papatasi, Sandfly (Phlebotomus spp.), Black blow fly (Phormia regina), Prosimulium yezoensis, Northern blowfly (Protophormia terraenovae), Przhevalskiana silenus, Apple maggot (Rhagoletis pomonella), Rhinoestrus spp., Flesh fly (Sarcophaga carnaria), Flesh fly (Sarcophaga peregrina), Sarcophaga spp., Black fly (Simulium ochraceum), Simulium reptans, Simulium spp.) Orange wheat blossom midge (Sitodiplosis mosellana), Stable fly (Stomoxys calcitrans), Stomoxys spp., Tabanus atratus, Tabanus bromius, Greenhead horse fly (Tabanus nigrovittatus), Tabanus spodopterus, Tabanus spp., Tabanus sudeticus, Horse fly (Tabanus trigonus), Moth fly (Telmatoscopus albipunctatus), Tipula paludosa, Tipula spp., Wilhelmia equine, Wilhelmia spp., Wohlfahrtia spp., etc. Order Hemiptera; green stink bug (Acrosternum hilare), pea aphid (Acyrthosiphon pisum), camellia spiny whitefly (Aleurocanthus camelliae), orange spiny whitefly (Aleurocanthus spiniferus), Indian cotton leafhopper (Amrasca devastans), California red scale (Aonidiella aurantii), cowpea aphid (Aphis craccivora), black bean aphid (Aphis fabae), soybean aphid (Aphis glycines), cotton aphid (Aphis gossypii), green apple aphid (Aphis pomi), spiraea aphid (Aphis spiraecola), pale green plant bug (Apolygus spinolae), grape leafhopper (Arboridia apicalis), foxglove aphid (Aulacorthum solani), Beardsley leafhopper (Balclutha saltuella), silverleaf whitefly (Bemisia argentifolii), sweetpotato whitefly (Bemisia tabaci), true chinch bug (Blissus leucopterus), leafcurl plum aphid (Brachycaudus helichrysi), cabbage aphid (Brachycaudusaphid (Brevicoryne brassicae), Oriental chinch bug (Cavelerius saccharivorus), Indian wax scale (Ceroplastes ceriferus), Red wax scale (Ceroplastes rubens), Walnut aphid (Chromaphis juglandicola), Bed bug (Cimex lectularius), Rice stink bug (Cletus punctiger), Citricola scale (Coccus pseudomagnoliarum), San jose scale (Comstockaspis perniciosa), Citrus whitefly (Dialeurodes citri), Asian citrus psyllid (Diaphorina citri), Dichelops furcatus (Dichelops furcatus), Russian wheat aphid (Diuraphis noxia), Sloe bug (Dolycoris baccarum), Giant margarodid scale (Drosicha corpulenta), Rosy apple aphid (Dysaphis plantaginea), Red cotton bug (Dysdercus cingulatus), Potato Leafhopper (Empoasca fabae), Empoasca nipponica (Empoasca nipponica), Tea green leafhopper (Empoasca onukii), Bean's smaller green leafhopper (Empoasca sakaii), GrapeLeafhopper (Epiacanthus stramineus), Wooly apple aphid (Eriosoma lanigerum), Cabbage bug (Eurydema rugosa), brown stink bug (Euschistus servus), Whitespotted spined bug (Eysarcoris aeneus), Eysarcoris lewisi (Eysarcoris lewisi), White-spotted stink bug (Eysarcoris ventralis), Tea scale (Fiorinia theae), Sheild bug (Glaucias subpunctatus), Island fleahopper (Halticus insularis), Brown marmorated stink bug (Halyomorpha halys), Mealy plum aphid (Hyalopterus pruni), Cottony cushion scale (Icerya purchasi), Small brown planthopper (Laodelphax striatellus), Rice bug (Leptocorisa chinensis), Turnip aphid (Lipaphis erysimi), Western tarnished plant bug (Lygus hesperus), Tarnished plant bug (Lygus lineolaris), Potato aphid (Macrosiphum euphorbiae), Aster leafhopper (Macrosteles fascifrons), Grape Leafhopper (Macrostelesstriifrons), Sugarcane spittlebug (Mahanarva fimbriolata), Blackmargined aphid (Monellia caryella), Green peach aphid (Myzus persicae), Lettuce aphid (Nasonovia ribisnigri), Onion aphid (Neotoxoptera formosana), Green rice leafhopper (Nephotettix cincticeps), Eastern green stink bug (Nezara antennata), Southern green stink bug (Nezara viridula), Brown rice planthopper (Nilaparvata lugens), Squash bug (Paradasynus spinosus), Cotton mealy bug (Phenacoccus solani), Redbanded stink bug (Piezodorus guildinii), Redbanded shield bug (Piezodorus hybneri), Citrus mealybug (Planococcus citri), Japanese mealybug (Planococcus kraunhiae), Brown-winged green bug (Plautia crossota), Peony scale (Pseudaonidia paeoniae), Cotton fleahopper (Pseudatomoscelis seriatus), Mulberry scale (Pseudaulacaspis pentagona), White peachscale (Pseudaulacaspis prunicola), Comstock mealybug (Pseudococcus comstocki), Grape mealybug (Pseudococcus maritimus), Pear sucker (Psylla pyrisuga), Blood-sucking bug (Rhodnius prolixus), Bird cherry-oat aphid (Rhopalosiphum padi), Rice root aphid (Rhopalosiphum rufiabdominalis), Rhopalid bug (Rhopalus maculatus), Bean bug (Riptortus clavatus), Greenbug (Schizaphis graminum), Japanese black rice bug (Scotinophora lurida), Corn leaf aphid (Sitobion akebiae), English grain aphid (Sitobion avenae), White-backed rice planthopper (Sogatella furcifera), Rice stink bug (Stenodema sibiricum), Sorghum plant bug (Stenotus rubrovittatus), Azalea lace bug (Stephanitis pyrioides), Seed bug (Togo hemipterus), Black citrus aphid (Toxoptera aurantii), Brown citrus aphid (Toxoptera citricida), Greenhouse whitefly (Trialeurodesvaporariorum), Mexican Kissing Bug (Triatoma dimidiata), Brazilian Kissing Bug (Triatoma infestans), Rice Leaf Bug (Trigonotylus caelestialium), Citrus Snow Scale (Unaspis citri), Euonymus Scale (Unaspis euonymi), Arrowhead Scale (Unaspis yanonensis), Grape Phylloxera (Viteus vitifolii), etc. Order Thysanoptera; Flower Thrips (Frankliniella intonsa), Western Flower Thrips (Frankliniella occidentalis), Greenhouse Thrips (Heliothrips haemorrhoidalis), Japanese Gall-forming Thrips (Ponticulothrips diospyrosi), Yellow Tea Thrips (Scirtothrips dorsalis), Melon Thrips (Thrips palmi), Onion Thrips (Thrips tabaci), etc. Orthoptera; Australian plague locust (Chortoicetes terminifera), Oriental mole cricket (Gryllotalpa orientalis), Migratory locust (Locusta migratoria), Lesser paddy grasshopper (Oxya japonica), Rice grasshopper (Oxya yezoensis), Desert locust (Schistocerca gregaria), Emma field cricket (Teleogryllus emma), etc., Dictyoptera; German cockroach (Blattella germanica), Formosan subterranean termite (Coptotermes formosanus), Daikoku dry-wood termite (Cryptotermes domesticus), Western dry-wood termite (Incisitermes minor), Black-winged subterranean termite (Odontotermes formosanus), American cockroach (Periplaneta americana), Smoky-brown cockroach (Periplaneta fuliginosa), Japanese cockroach (Periplaneta japonica), Japanese subterranean termite (Reticulitermes speratus), etc., Order Isoptera; such as Coptotermes formosanus (Coptotermes formosanus), Reticulitermes speratus (Reticulitermes speratus), Odontotermes formosanus (Odontotermes formosanus), etc. Mites (Acari); Cyclamen mite (Phytonemus pallidus), Broad mite (Polyphagotarsonemus latus), Tarsonemus bilobatus (Tarsonemus bilobatus), Penthaleus erythrocephalus (Penthaleus erythrocephalus), Winter grain mite (Penthaleus major), Rice spider mite (Oligonychus shinkajii), Citrus red mite (Panonychus citri), Mulberry mite (Panonychus mori), European red mite (Panonychus ulmi), Kanzawa spider mite (Tetranychus kanzawai), Two-spotted spider mite (Tetranychus urticae), Acaphylla theavagrans (Acaphylla theavagrans), Dry bulb mite (Aceria tulipae), Tomato erineum mite (Aculops lycopersici), Pink citrus rust mite (Aculops pelekassi), Apple rust mite (Aculus schlechtendali), Eriophyes chibaensis (Eriophyes chibaensis), Phyllocoptruta oleivora (Phyllocoptruta oleivora), Bulb mite (Rhizoglyphus robini), Mold mite (Tyrophagus putrescentiae), Spinach mold mite (Tyrophagus similis (Tyrophagussimilis), Acarapis spp., Honey bee tracheal mite (Acarapis woodi), Acarus spp., Lone star tick (Amblyomma americanum), Cayenne tick (Amblyomma cajennense), South African bont tick (Amblyomma hebraeum), Gulf coast tick (Amblyomma maculatum), Amblyomma spp., Tropical bont tick (Amblyomma variegatum), Fowl tick (Argas persicus), Pigeon tick (Argas reflexus), Argas spp., Blue cattle tick (Boophilus annulatus), Boophilus (Boophilus) calceratus, African blue tick (Boophilus decoloratus), Tropical cattle tick (Boophilus microplus), Boophilus spp., Caloglyphus spp., Chelacaropsis moorei, Cheyletiella blakei, Rabbit fur mite (Cheyletiella parasitovorax), Cheyletiella spp., Cheyletiella yasguri, Cheyletus eruditus, Cheyletus malaccensis, Chorioptic mange mite (Chorioptes bovis), Chorioptes spp.spp.), Cytodites spp., Cattle follicle mite (Demodex bovis), Demodex caballi, Dog follicle mite (Demodex canis), Demodex caprae, Cat follicle mite (Demodex cati), Demodex equi, Face mite (Demodex folliculorum), Demodex ovis, Demodex spp., Sarcoptes suis mite (Demodex suis), Winter tick (Dermacentor albipictus), Rocky Mountain wood tick (Dermacentor andersoni), Ornate sheep tick (Dermacentor marginatus), Meadow tick (Dermacentor pictus), Ornate dog tick (Dermacentor reticulatus), Dermacentor spp., American dog tick (Dermacentor variabilis), Poultry red mite (Dermanyssus gallinae), Dermanyssus spp., American house dust mite (Dermatophagoides farina), House dust mite (Dermatophagoides pteronyssinus), Eutrombicula wichmanni, Storage mite (Glycyphagus destructor), House itch mite (Glycyphagusdomesticus), Haemaphysalis cinnabarina, Common rodent tick (Haemaphysalis concinna), Yellow dog tick (Haemaphysalis leachi), Bush tick (Haemaphysalis longicornis), Haemaphysalis otophila, Red sheep tick (Haemaphysalis punctate), Haemophysalis spp., Haplochthonius simplex, Trombiculid mite (Helenicula miyagawai), Tortoise tick (Hyalomma aegyptium), Hyalomma anatolicum, Bont-legged tick (Hyalomma marginatum), Hyalomma mauritanicus, Hyalomma spp., Small smooth bont-legged tick (Hyalomma transiens), Hypodectes spp., Dog tick (Ixodes canisuga), Hedgehog tick (Ixodes hexagonus), Australian paralysis tick (Ixodes holocyclus), Western black-legged tick (Ixodes pilosus), castor bean tick (Ixodes ricinus), Karoo paralysis tick (Ixodes rubicundus), Deer tick (Ixodes scapularis), Ixodes spp., Ixodesspp.), Knemidocoptes spp., Laminosioptes spp., Leptotrombidium akamushi, Leptotrombidium pallida, Leptotrombidium scutellare, Listrophorus spp., Megninia cubitalis, Myobia spp., Neoschoengastia xerothermobia, Neotrombicula autumnalis, Neotrombicula desaleri, Notoedres cati, Notoedres spp., Ornithocheyletia spp., Ornithodorus moubata, Ornithodorus spp., Ornithonyssus bursa, Ornithonyssus spp., Ornithonyssus sylviarum, Otobius megnini, Otobius spp., Otodectes cynotis, Otodectes spp., Pneumonyssoides caninum, Pneumonyssoides mange, Pneumonyssus spp., Pneumonyssus spp., Psorergatesspp.), Psoroptic mite (Psoroptes communis), Rabbit ear mite (Psoroptes cuniculi), Psoroptes equi, Sheep scab mite (Psoroptes ovis), Psoroptes ovis, Psoroptes spp., Feather mite (Pterolichus obtusus), Pterolichus spp., Raillieti a spp.), Brown ear tick (Rhipicephalus appendiculatus), Brown ear tick (Rhipicephalus bursa), Rhipicephalus capensis, Asian blue tick (Rhipicephalus evertsi), Kennel tick (Rhipicephalus sanguineus), Rhipicephalus spp., Rhipicephalus turanicus, Rhipicephalus zambeziensis, Sarcoptes bovis, Sarcoptes equi, Sarcoptes ovis, Sarcoptes rupicaprae(=S. caprae), Itch mite (Sarcoptes scabiei), Sarcoptes spp., Sarcoptes suis, Itch mite (Sarcoptis canis), Sternostoma spp., Trombicula akamushi, Trombicula spp., Cheese mite (Tyrophagus putrescentiae), Tyrophagus spp., Varroa mite (Varroa jacobsoni), Varroa spp., etc. Order Anoplurida; Short-nosed cattle louse (Haematopinus eurysternus), Tail switch louse (Haematopinus quadripertusus), species of Haematopinus spp., Large pig louse (Haematopinus suis), Buffalo louse (Haematopinus tuberculatus), Rabbit louse (Haemodipsus ventricosus), Dog sucking louse (Linognathus setosus), species of Linognathus spp., Long-nosed cattle louse (Linognathus vituri), Head louse (Pediculus humanus), species of Pediculus spp., Mouse louse (Polyplax serratus), Crab louse (Pthirus pubis), species of Pthirus spp., Little blue cattle louse (Solenopotes capillatus), species of Solenopotes spp., etc., Order Mallophaga; Goat biting louse (Bovicola caprae), Bovicola limbata, Sheep body louse (Bovicola ovis), Bovicola spp., Chicken head louse (Cuclotogaster heterographa), Cattle chewing louse (Damalinia bovis), Felicola spp., Cat louse (Felicola subrostrata), Brown chicken louse (Goniodes dissmilis), Fluff louse (Goniodes gallinae), Large hen louse (Goniodes gigas), Lepikentron ovis, Lepikentron spp., Wing louse (Lipeurus caponis), Body louse (Menacanthus cornutus), Small body louse (Menacanthus pallidulus), Menacanthus spp., Chicken body louse (Menacanthus stramineus), Chicken shaft louse (Menopon gallinae), Menopon spp., Dog biting louse (Trichodectes canis), Trichodectes spp., Werneckiella equi, Werneckiella spp., etc., Order Siphonaptera; hen flea (Ceratophyllus gallinae), dog flea (Ctenocephalides canis), cat flea (Ctenocephalides felis), sticktight flea (Echidnophaga gallinacean), human flea (Pulex irritans), chigoe flea (Tunga penetrans), Oriental rat flea (Xenopsylla cheopis), etc. Other parasites include Monogenea; Benedenia epinepheli, Benedenia hoshinai, Benedenia sekii, Benedenia seriolae, Bivagina tai, Caligus curtus (Sea louse), Caligus elongates, Caligus labaracis, Caligus longipedis, Caligus orientalis, Caligus teres, Dactylogyrus spp., Gyrodactylus spp., Heteraxine heterocerca, Heterobothrium okamotoi, Lamellodiscus spp., Lepeophtheirus cuneifer, Lepeophtheirus hippoglossi, Lepeophtheirus pectoralis, Lepeophtheirus salmonis (salmon louse), Microcotyle sebastis, Microcotyle sebastisci, Neobenedenia, Neobenedenia congeri, Neobenedenia girellae, Neoheterobothrium hirame, Polystoma spp., Pseudocaligus fugu, Zeuxapta japonica, etc. Cestoda; Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Bothridium spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diphyllobothrium erinacei (manson's tapeworm), Diphyllobothrium latum (fish tapeworm), Diphyllobothrium spp., Diphyllogonoporus spp., Diplopylidium spp., Dipylidium caninum (dog tapeworm), Dipylidium spp., Echinococcus granulosus (dog tapeworm), Echinococcus multilocularis (fox tapeworm), Echinococcus spp., Echinocotyle spp., Echinolepsis spp., Hydatigera spp., Hymenolepis diminuta, Hymenolepis spp., Joyeuxiella spp., Ligura spp., Mesocestoides spp., Moniezia benedeni, Moniezia spp., Paranoplocephala spp., Raillietina spp., Schistocephalus spp., Spirometra spp., Stilesia spp.) Taenia saginata (beef tapeworm), Taenia solium (pork tapeworm), Taenia spp., Taenia taeniaeformis (cat tapeworm), Thysaniezia spp., Thysanosomsa spp., etc. Trematoda; Austrobilharzia spp., Brachylaema spp., Calicophoron spp., Catatropis spp., Chinese liver fluke (Clonorchis sinensis), Clonorchis spp., Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrema coelomaticum (small pancreatic fluke), Eurytrema pancreaticum (pancreas fluke), Eurytrema spp., Fasciola gigantica (giant liver fluke), Fasciola hepatica (sheep liver fluke), Fasciola spp., Fasciolides spp., Fasciolopsis buski (large intestinal fluke), Fasciolopsis spp., Fischoederius spp., Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp.) Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Ornithobilharzia spp., Paragonimus spp., Paragonimus westermani (Oriental lung fluke), Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma haematobium, Schistosoma japonicum, Schistosoma mansoni, Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp., etc., Nematoda; Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Anisakis spp., Ascaridia galli, Ascaridia spp., Ascaris spp., Ascaris suum, Aspiculuris spp., Brugia spp., Bunostomum spp., Capillaria spp., Chabertia spp., Cooperia oncophora (intestinal worm), Cooperia spp., Crenosoma spp., Cyathostoma spp.)、Cyclococercus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Dirofilaria immitis, Dirofilaria spp., Dracunculus spp., Draschia spp., Elaphostrongylus spp., Enoplida, Enterobius spp., Filaroides spp., Filicollis spp., Globocephalus spp., Gnathostoma spp., Gongylonema spp., Gyalocephalus spp., Habronema spp., Haemonchus contortus (Barber's pole worm), Haemonchus spp., Heterakis spp., Hyostrongylus spp., Litomosoides spp., Loa spp., Macracanthorhynchus spp., Marshallagia spp., Metastrongylus spp. (pig lungworms), Micronema spp., Moniliformis spp., Muellerius spp., Nematodirus spp., Neostrongylus spp., Obeliscoides spp.)、Oeophagostomum dentatum, Oesophagodontus spp., Oesophagostomum radiatum, Oesophagostomum spp., Ollulanus spp., Onchocerca gibsoni, Onchocerca spp., Ostertagia ostertagi (Brown stomach worm), Ostertagia spp., Oxyuris spp., Parabronema spp., Paracrenosoma spp., Parafilaria spp., Parafilaroides spp., Parascaris spp., Parelaphostrongylus spp., Passalurus spp., Physaloptera spp., Pneumostrongylus spp., Poteriostomum spp., Prostenorchis spp., Protostrongylus spp., Setaria spp., Spicocaulus spp., Stephanofilaria spp., Stephanurus spp., Strongyloides spp., Strongylus spp., Syngamus spp., Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Trichinella spp., Trichomosoides spp.) Trichonema spp., Trichostrongylus colubriformis, Trichostrongylus spp., Trichuris spp., Triodontophorus spp., Uncinaria spp., Wuchereria spp., etc. Protozoa; Babesis spp., Eimeria acervulina, Eimeria bovis, Eimeria brunette, Eimeria maxima, Eimeria necatrix, Eimeria ovinoidalis, Eimeria spp., Eimeria tenella, Entamoeba histolytica, Giardia spp., Histomanas spp., Plasmodium spp., Theileria spp., Toxoplasma spp., Trichomonadidae spp., Trypanosomsa cruzi, etc.

[0091] Furthermore, the compounds of the present invention are also effective against pests that have developed resistance to existing insecticides such as organophosphorus compounds, carbamate compounds, and pyrethroid compounds.

[0092] That is, the compounds of the present invention can effectively control pests belonging to insects such as the order Mallophaga (chewing lice), Dermaptera (earwigs), Orthoptera (grasshoppers), Isoptera (termites), Neuroptera (lacewings), Hemiptera (true bugs and leafhoppers), Lepidoptera (butterflies and moths), Coleoptera (beetles), Hymenoptera (ants, bees, and wasps), Diptera (flies), Isoptera (termites), Anoplura (sucking lice), etc., crustaceans such as Lepidoptera, Isopoda, and Decapoda, mites, gastropods, cestodes, trematodes, nematodes, protozoa, etc. at low concentrations.

[0093] On the other hand, the compounds of the present invention have extremely useful characteristics with almost no adverse effects on mammals, fish, crustaceans, and beneficial insects (useful insects such as honeybees and bumblebees, and natural enemies such as ladybugs, aphidophagous hoverflies, parasitoid flies, minute pirate bugs, and spider mites).

[0094] When using the compounds of the present invention, they are usually mixed with a suitable solid carrier or liquid carrier, and further, if desired, surfactants, penetrants, spreading agents, thickeners, antifreezing agents, binders, anti-caking agents, disintegrants, defoaming agents, preservatives, decomposition inhibitors, etc. are added to prepare formulations of any dosage form such as soluble concentrate, emulsifiable concentrate, wettable powder, water soluble powder, water dispersible granule, water soluble granule, suspension concentrate, concentrated emulsion, suspoemulsion, microemulsion, dustable powder, granule, tablet, emulsifiable gel, etc. for practical use. Also, from the viewpoints of labor saving and safety improvement, the formulations of any of the above dosage forms can be enclosed in water-soluble packages such as water-soluble capsules and water-soluble film bags for supply.

[0095] Examples of the solid carrier include natural minerals such as quartz, calcite, sepiolite, dolomite, chalk, kaolinite, pyrophyllite, sericite, halloysite, metahalloysite, kibushi clay, frog-eye clay, pottery stone, zeolite, allophane, shirasu, kirara, talc, bentonite, activated clay, acid clay, pumice, attapulgite, zeolite, diatomaceous earth; fired products of natural minerals such as fired clay, perlite, shirasu balloon, vermiculite, attapulgus clay, fired diatomaceous earth; inorganic salts such as magnesium carbonate, calcium carbonate, sodium carbonate, sodium hydrogen carbonate, ammonium sulfate, sodium sulfate, magnesium sulfate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate, potassium chloride; saccharides such as glucose, fructose, sucrose, lactose; polysaccharides such as starch, powdered cellulose, dextrin; organic substances such as urea, urea derivatives, benzoic acid, salts of benzoic acid; plants such as wood powder, cork powder, corn cob, walnut shell, tobacco stem; fly ash, white carbon (e.g., hydrated synthetic silica, anhydrous synthetic silica, hydrated synthetic silicate, etc.), fertilizers; and the like.

[0096] Examples of the liquid carrier include, for example, xylene, alkyl (C 9 or C 10 etc.) benzene, phenylxylene ethane, alkyl (C 1 or C 3Aromatic hydrocarbons such as naphthalene; aliphatic hydrocarbons such as machine oil, normal paraffin, isoparaffin, and naphthene; mixtures of aromatic and aliphatic hydrocarbons such as kerosene; alcohols such as ethanol, isopropyl alcohol, cyclohexanol, phenoxyethanol, and benzyl alcohol; polyhydric alcohols such as ethylene glycol, propylene glycol, diethylene glycol, hexylene glycol, polyethylene glycol, and polypropylene glycol; ethers such as propyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, and propylene glycol monophenyl ether; ketones such as acetophenone, cyclohexanone, and γ-butyrolactone; esters such as fatty acid methyl ester, dialkyl succinate, dialkyl glutamate, dialkyl adipate, and dialkyl phthalate; acid amides such as N-alkyl (C 1 , C 8 or C 12 etc.) pyrrolidone; oils and fats such as soybean oil, linseed oil, rapeseed oil, coconut oil, cottonseed oil, and castor oil; dimethyl sulfoxide, water; etc.

[0097] These solid carriers and liquid carriers may be used alone or in combination of two or more.

[0098] Examples of surfactants include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl (mono- or di-) phenyl ethers, polyoxyethylene (mono-, di- or tri-) styryl phenyl ethers, polyoxyethylene polyoxypropylene block copolymers, polyoxyethylene fatty acid (mono- or di-) esters, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, castor oil ethylene oxide adducts, acetylene glycols, acetylene alcohols, ethylene oxide adducts of acetylene glycols, ethylene oxide adducts of acetylene alcohols, alkyl glycosides; anionic surfactants such as alkyl sulfate salts, alkylbenzene sulfonate salts, lignin sulfonate salts, alkyl sulfosuccinate salts, naphthalene sulfonate salts, alkylnaphthalene sulfonate salts, salts of formalin condensates of naphthalene sulfonic acids, salts of formalin condensates of alkylnaphthalene sulfonic acids, polyoxyethylene alkyl ether sulfuric or phosphoric acid ester salts, polyoxyethylene (mono- or di-) alkyl phenyl ether sulfuric or phosphoric acid ester salts, polyoxyethylene (mono-, di- or tri-) styryl phenyl ether sulfuric or phosphoric acid ester salts, polycarboxylate salts (e.g., polyacrylate salts, polymaleate salts, copolymers of maleic acid and olefins, etc.), polystyrene sulfonate salts; cationic surfactants such as alkylamine salts, alkyl quaternary ammonium salts; amphoteric surfactants such as amino acid type, betaine type; silicone-based surfactants, fluorine-based surfactants; and the like.

[0099] The content of these surfactants is not particularly limited, but is preferably in the range of usually 0.05 to 20 parts by mass with respect to 100 parts by mass of the formulation of the present invention. Further, these surfactants may be used alone or in combination of two or more.

[0100] The application dosage of the compound of the present invention varies depending on the application scenario, application time, application method, cultivated crops, etc., but usually, as the active ingredient amount, about 0.005 to 50 kg per hectare (ha) is appropriate.

[0101] On one hand, when using the compound of the present invention for controlling internal or external parasites of mammals and birds as livestock and pets, an effective amount of the compound of the present invention, together with formulation additives, can be administered orally; parenterally such as by injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); transdermally such as by dipping, spraying, bathing, washing, pouring-on and spotting-on, dusting, etc.; intranasally; and so on. The compound of the present invention can also be administered by molded products using chips, plates, bands, collars, ear marks, limb bands, labeling devices, etc.

[0102] For administration, the compound of the present invention can be made into any dosage form suitable for the administration route.

[0103] When using the compound of the present invention to control external or internal parasites, the preferred dosage of the compound of the present invention (1) as the active ingredient depends on the type of target parasite to be controlled, the species of the target animal to be administered, the administration method, etc. Usually, it is 0.01 - 100 mg / kg, preferably 0.01 - 50 mg / kg per kg of the body weight of the target animal to be administered. In particular, the dosage for dogs can vary depending on the type or age of the target dog or the external parasite to be controlled, but it is usually 1 - 5000 mg / kg, preferably 1 - 100 mg / kg per kg of the live body weight of the target dog.

[0104] When using the compound of the present invention to control external or internal parasites by administration, the administration interval depends on the type of target parasite to be controlled, the species of the target animal to be administered, the administration method, etc. Usually, it can be arbitrarily set within the range of once a day to once a year. Preferably, it is once a week to once every six months, more preferably once a day (24 hours), once a month, once a month, once every two months, once every three months or once every six months.

[0105] When the compound of the present invention is used for controlling external parasites of dogs, as the timing of administering the compound of the present invention to dogs, for example, it can be orally administered to dogs at a timing immediately before 30 minutes from the start of feeding or 120 minutes after the end of feeding. The 30 minutes before the start of feeding and 120 minutes after the end of feeding mentioned here are based on the act of ingesting the food given to dogs for the purpose of nutrition intake. For example, when the feeding time of a dog is 20 minutes, the specified time is a total of 170 minutes from 30 minutes before the start of feeding to 120 minutes after the end of feeding based on the eating act. This includes the case where the feeding is once interrupted during the meal and the feeding is resumed after orally administering the compound of the present invention. In the present specification, "feeding" means the act of an animal eating food.

[0106] Generally, the number of daily feedings of dogs varies depending on the dog breed, age, and habits. Usually, dogs less than six months old are fed 3 to 4 times a day, dogs from six months to less than one year old are fed 2 to 3 times a day, adult dogs about 1 to 5 years old are fed 2 times a day, and old dogs over 6 years old are fed about 2 to 3 times a day. In the present invention, "feeding" means the eating act for the purpose of obtaining nutrition, and does not include the act of giving food for the so-called training or discipline of dogs.

[0107] As any dosage form to be prepared, there are solid preparations such as powders, granules, wettable powders, pellets, tablets, boluses, capsules, molded products containing the active compound, etc.; liquid preparations such as injection solutions, oral solutions, solutions used on the skin or in body cavities, etc.; solution preparations such as pour-on agents, spot-on agents, flowable agents, emulsions, etc.; semi-solid preparations such as ointments, gels, etc.

[0108] As the dosage form when the compound of the present invention is orally administered, for example, there are solid preparations such as tablets, chewables, capsules, pills, boluses, granules, powders, etc.; semi-solid preparations such as pastes, gels, etc.; liquid preparations such as drinks, etc.

[0109] In addition, as dosage forms for transdermal administration, for example, solid preparations such as powders; semi-solid preparations such as creams, salves and ointments, pastes, gels; liquid preparations such as sprays, aerosols, solutions and emulsions, suspensions, lotions; etc. can be mentioned.

[0110] Furthermore, as dosage forms for administration by injection, for example, liquid preparations such as solutions and emulsions, suspensions; etc. can be mentioned, and as dosage forms for nasal administration, for example, liquid preparations such as aerosols; etc. can be mentioned.

[0111] In addition, as dosage forms for spraying treatment in the breeding environment of animals such as livestock houses, for example, solid preparations such as wettable powders, dusts, granules; liquid preparations such as emulsions, suspension concentrates; etc. can be mentioned.

[0112] Note that the preparations used in the parasitic control agent of the present invention are not limited to only these dosage forms.

[0113] The solid preparation can be used as it is for oral administration, or diluted with water and used by transdermal administration, spraying treatment in the breeding environment of animals such as livestock houses, etc.

[0114] The solid preparation used for oral administration can be prepared by mixing the compound (1) of the present invention or a salt thereof with one or more excipients and binders suitable for oral administration, and further, if necessary, physiologically acceptable additives such as lubricants, disintegrants, dyes, pigments, etc., and molding into a desired shape.

[0115] Examples of the excipient and binder include sugars or sugar derivatives such as lactose, sucrose, mannitol, sorbitol, etc.; starches such as corn starch, wheat starch, rice starch, potato starch, etc.; celluloses or cellulose derivatives such as methylcellulose, carboxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, etc.; proteins or protein derivatives such as zein, gelatin, etc.; synthetic polymer compounds such as honey, gum arabic paste, polyvinyl alcohol, polyvinylpyrrolidone, etc.

[0116] Examples of the lubricant include magnesium stearate, etc. Examples of the disintegrant include cellulose, agar, alginic acid, crosslinked polyvinylpyrrolidone, carbonate, etc.

[0117] Furthermore, among the solid preparations used for oral administration, especially in the case of solid forms such as chewable agents, additives that impart the taste, texture, and flavor preferred by the animals to be administered are also used. However, the carriers and additives used in the solid preparations of the anthelmintic composition are not limited to these only.

[0118] The liquid preparation can be administered as it is by percutaneous or injection, or can be mixed with feed for oral administration, diluted with water for oral or percutaneous administration, or sprayed on the breeding environment of animals such as livestock houses.

[0119] The injection solution can be administered intravenously, intramuscularly, and subcutaneously. The injection solution can be prepared by dissolving the active compound in a suitable solvent and adding additives such as solubilizers, acids, bases, buffer salts, antioxidants, protective agents, etc. if necessary.

[0120] Examples of the suitable solvent include water, ethanol, butanol, benzyl alcohol, glycerin, propylene glycol, polyethylene glycol, N-methylpyrrolidone and mixtures thereof, physiologically acceptable vegetable oils, synthetic oils suitable for injection, etc.

[0121] Examples of solubilizers include polyvinylpyrrolidone, polyoxyethylated castor oil, polyoxyethylated sorbitan esters, and the like.

[0122] Examples of preservatives include benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters, n-butanol, and the like.

[0123] The oral liquid preparation can be administered directly or after dilution. It can be prepared in the same manner as the injection liquid preparation.

[0124] Flowable agents, emulsions, etc. can be administered directly or after dilution, percutaneously, or in environmental treatment.

[0125] The liquid preparation used on the skin can be administered by dropping, spreading, rubbing in, spraying, scattering, or by dipping (immersing, bathing, or washing). These liquid preparations can be prepared in the same manner as the injection liquid preparation.

[0126] Pour-on agents and spot-on agents can be dropped or sprayed onto a limited area of the skin, thereby immersing the active compound in the skin and allowing it to act systemically.

[0127] Pour-on agents and spot-on agents can be prepared by dissolving, suspending, or emulsifying the active ingredient in a suitable dermatologically compatible solvent or solvent mixture. If necessary, adjuvants such as surfactants, colorants, absorption promoters, antioxidants, light stabilizers, adhesives, etc. can be added.

[0128] Suitable solvents include water, alkanol, glycol, polyethylene glycol, polypropylene glycol, glycerin, benzyl alcohol, phenylethanol, phenoxyethanol, ethyl acetate, butyl acetate, benzyl benzoate, dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, acetone, methyl ethyl ketone, aromatic and / or aliphatic hydrocarbons, vegetable or synthetic oils, DMF (N,N-dimethylformamide), liquid paraffin, light liquid paraffin, silicone, dimethylacetamide, N-methylpyrrolidone, or 2,2-dimethyl-4-oxy-methylene-1,3-dioxolane, etc.

[0129] Absorption promoters include DMSO (dimethyl sulfoxide), isopropyl myristate, dipropylene glycol pelargonate, silicone oil, aliphatic esters, triglycerides, fatty alcohols, etc.

[0130] Antioxidants include sulfites, metabisulfites, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, tocopherol, etc.

[0131] The emulsion can be administered orally, transdermally, or by injection. The emulsion can be prepared by dissolving the active ingredient in a hydrophobic or hydrophilic phase, and homogenizing this with a solvent of the other phase, together with a suitable emulsifier and, if necessary, auxiliary agents such as colorants, absorption promoters, protective agents, antioxidants, light-shielding agents, thickening substances, etc.

[0132] Examples of the hydrophobic phase (oil) include paraffin oil, silicone oil, sesame oil, almond oil, castor oil, synthetic triglyceride, ethyl stearate, di-n-butyl adipate, hexyl laurate, dipropylene glycol pelargonate, ester of branched short-chain fatty acid and saturated fatty acid with chain length C16-C18, isopropyl myristate, isopropyl palmitate, caprylic / capric acid ester of saturated fatty alcohol with chain length C12-C18, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, wax-like fatty acid ester, dibutyl phthalate, diisopropyl adipate, isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol, etc.

[0133] Examples of the hydrophilic phase include water, propylene glycol, glycerin, sorbitol, etc.

[0134] Examples of the emulsifier include nonionic surfactants such as polyoxyethylated castor oil, polyoxyethylated sorbitan monooleate, sorbitan monostearate, glycerin monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether; amphoteric surfactants such as disodium N-lauryl-β-iminodipropionate, lecithin; anionic surfactants such as sodium lauryl sulfate, fatty alcohol sulfate ether, monoethanolamine salt of mono / dialkyl polyglycol orthophosphate ester; cationic surfactants such as cetyltrimethylammonium chloride; etc.

[0135] Examples of other auxiliary agents include carboxymethyl cellulose, methyl cellulose, polyacrylate, alginate, gelatin, gum arabic, polyvinyl pyrrolidone, polyvinyl alcohol, copolymer of methyl vinyl ether and maleic anhydride, polyethylene glycol, wax, colloidal silica, etc.

[0136] The semi-solid preparation can be administered by applying or spreading on the skin or introducing it into a body cavity. The gel can be prepared by adding a thickener sufficient to produce a transparent substance having an ointment-like viscosity to the solution prepared as described above for the injection solution.

[0137] Next, formulation examples using the compound of the present invention are shown. However, the formulation examples of the preparation containing the compound of the present invention are not limited thereto. In the following formulation examples, "parts" means parts by mass.

[0138] 〔Wettable powder〕 Compound of the present invention 0.1 - 80 parts Solid carrier 5 - 98.9 parts Surfactant 1 - 10 parts Others 0 - 5 parts Examples of others include, for example, anti-caking agents, anti-decomposition agents, etc.

[0139] 〔Emulsion〕 Compound of the present invention 0.1 - 30 parts Liquid carrier 45 - 95 parts Surfactant 4.9 - 15 parts Others 0 - 10 parts Examples of others include, for example, spreading agents, anti-decomposition agents, etc.

[0140] 〔Suspension〕 Compound of the present invention 0.1 - 70 parts Liquid carrier 15 - 98.89 parts Surfactant 1 - 12 parts Others 0.01 - 30 parts Examples of others include, for example, anti-freezing agents, thickening agents, etc.

[0141] 〔Granular wettable powder〕 Compound of the present invention 0.1 - 90 parts Solid carrier 0 - 98.9 parts Surfactant 1 - 20 parts Others 0 - 10 parts Examples of others include, for example, binders, anti-decomposition agents, etc.

[0142] [Liquid formulation] 0.01 - 70 parts of the compound of the present invention 20 - 99.99 parts of liquid carrier 0 - 10 parts of others Examples of others include antifreezing agents, spreading agents, etc.

[0143] [Granule formulation] 0.01 - 80 parts of the compound of the present invention 10 - 99.99 parts of solid carrier 0 - 10 parts of others Examples of others include binders, decomposition inhibitors, etc.

[0144] [Powder formulation] 0.01 - 30 parts of the compound of the present invention 65 - 99.99 parts of solid carrier 0 - 5 parts of others Examples of others include drift inhibitors, decomposition inhibitors, etc.

[0145] Next, formulation examples containing the compound of the present invention as an active ingredient are shown more specifically, but the present invention is not limited thereto. The compound No. 1 - 001 of the present invention shown below is N-(5-fluoropyridin-2-yl)-5-(3-(2-fluoropyridin-4-yl)-1,2,4-oxadiazol-5-yl)-3,7-dioxo-2,3,6,7-tetrahydro-5H-oxazolo[3,2-a]pyr which means lysine-8-carboxamide described in Synthesis Example 1 below.

[0146] [Formulation Example 1] Wettable powder 20 parts of the compound No. 1 - 001 of the present invention 74 parts of pyrophyllite 4 parts of Solpol 5039 (Trade name of Toho Chemical Industry Co., Ltd., a mixture of nonionic surfactant and anionic surfactant) 2 parts of Carplex #80D (Trade name of Shionogi & Co., Ltd., synthetic hydrous silicic acid) The above is uniformly mixed and pulverized to obtain a wettable powder.

[0147] 〔Formulation Example 2〕Emulsion 5 parts of Compound No. 1-001 of the present invention 75 parts of xylene 15 parts of N-methylpyrrolidone 5 parts of Solpol 2680 (Trade name of Toho Chemical Industry Co., Ltd., a mixture of nonionic surfactant and anionic surfactant) The above is uniformly mixed to obtain an emulsion.

[0148] 〔Formulation Example 3〕Suspension 25 parts of Compound No. 1-001 of the present invention 10 parts of Agrisol S-710 (Trade name of Kao Corporation, nonionic surfactant) 0.5 part of Lennox 1000C (Trade name of Toho Chemical Industry Co., Ltd., anionic surfactant) 0.2 part of xanthan gum 64.3 parts of water After uniformly mixing the above, it is wet pulverized to obtain a suspension.

[0149] 〔Formulation Example 4〕Granular wettable powder 75 parts of Compound No. 1-001 of the present invention 5 parts of Hitenol NE-15 (Trade name of Daiichi Kogyo Seiyaku Co., Ltd., anionic surfactant) 10 parts of Vanirex N (Trade name of Nippon Paper Industries Co., Ltd., anionic surfactant) 10 parts of Carplex #80D (Trade name of Shionogi & Co., Ltd., synthetic hydrous silicic acid) After uniformly mixing and pulverizing the above, a small amount of water is added, stirred and mixed, granulated with an extrusion granulator, and dried to obtain a granular wettable powder.

[0150] 〔Formulation Example 5〕Granule 5 parts of Compound No. 1-001 of the present invention 50 parts of bentonite 45 parts of talc After uniformly mixing and pulverizing the above, add a small amount of water, stir and mix, granulate with an extrusion granulator, and dry to obtain granules.

[0151] 〔Formulation Example 6〕Powder 3 parts of Compound No. 1-001 of the present invention 0.5 part of Carplex #80D (Trade name of Shionogi & Co., Ltd., synthetic hydrous silicic acid) 95 parts of kaolinite 1.5 parts of diisopropyl phosphate Uniformly mix and pulverize the above to obtain a powder.

[0152] When in use, dilute the above preparation 1 to 10,000 times with water or spray it directly without dilution.

[0153] 〔Formulation Example 7〕Hydrating agent preparation 25 parts of Compound No. 1-001 of the present invention 1 part of sodium diisobutylnaphthalenesulfonate 10 parts of calcium n-dodecylbenzenesulfonate 12 parts of alkylaryl polyglycol ether 3 parts of sodium salt of naphthalenesulfonic acid formalin condensate 1 part of emulsion type silicone 3 parts of silicon dioxide 45 parts of kaolin 〔Formulation Example 8〕Water-soluble thickener preparation 20 parts of Compound No. 1-001 of the present invention 3 parts of polyoxyethylene lauryl ether 3.5 parts of sodium dioctyl sulfosuccinate 37 parts of dimethyl sulfoxide 36.5 parts of 2-propanol 〔Formulation Example 9〕Liquid for spraying 2 parts of Compound No. 1-001 of the present invention 10 parts of dimethyl sulfoxide 35 parts of 2-propanol 53 parts of acetone 〔Formulation Example 10〕Liquid for transdermal administration 5 parts of Compound No. 1-001 of the present invention 50 parts of hexylene glycol 45 parts of 2-propanol [Formulation Example 11] Solution for transdermal administration 5 parts of Compound No. 1-001 of the present invention 50 parts of propylene glycol monomethyl ether 45 parts of dipropylene glycol [Formulation Example 12] Solution for transdermal administration (dropwise) 2 parts of Compound No. 1-001 of the present invention 98 parts of light liquid paraffin [Formulation Example 13] Solution for transdermal administration (dropwise) 2 parts of Compound No. 1-001 of the present invention 58 parts of light liquid paraffin 30 parts of olive oil 9 parts of O.D.O (Product name of Nisshin OilliO Group, medium-chain fatty acid oil) 1 part of Shin-Etsu silicone In addition, when the compound of the present invention is used as an agricultural or veterinary drug, it may be mixed with other types of drugs during formulation or application as necessary. By mixing and applying, cost reduction due to reduction of the application dose, expansion of the control spectrum due to the synergistic effect of the mixed drugs, and higher pest control effect can be expected. At this time, combination with a plurality of known drugs at the same time is also possible.

[0154] For example, examples of the types of agricultural drugs to be mixed and used with the compound of the present invention include, for example, compounds described in The Pesticide Manual, 18th edition, 2018 and The Pesticide Manual, 19th edition, 2021. Specific examples of the general names of antiparasitic drugs and antibiotics to be mixed and used as veterinary drugs are as follows, but are not necessarily limited to these.

[0155] Insecticides: abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, acynonapyr, afidopyropen, afoxolaner, alanycarb, aldicarb, allethrin, alpha-cypermethrin, alpha-endosulfan, amidoflumet, amitraz, azamethiphos, azinphos-ethyl, azinphos-methyl, azocyclotin, bacillus thuringiensis, bendiocarb, benfluthrin, benfuracarb, bensultap, benzoximate, benzpyrimoxan, beta-cyfluthrin, beta-cypermethrin, bifenazate, bifenthrin, bioallethrin, biresmethrin, bistrifluron, broflanilide, bromopropylate, buprofezin, butocarboxim, carbaryl, carbofuran, carbosulfan, cartap, chinomethionat, chlorantraniliprole, chlorethxyfos,Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorobezilate, Chloroprallethrin, Chlorpyrifos, Chlorpyrifos-methyl, Chromafenozide, Clofentezine, Clothianidin, Cyanophos, Cyantraniliprole, Cyclaniliprole, Cycloprothrin, Cyenopyrafen, Cyetpyrafen, Cyflumetofen, Cyfluthrin, Cyhalodiamide, Cyhalothrin, Cyhexatine, Cypermethrin, Cyphenothrin, Cyproflanilide, Cyromazine, Deltamethrin, Diacloden, Diafenthiuron, Diazinon, Dichlorvos, Dicloromezotiaz, Dicofol, Dienochlor, Diflovidazin, Diflubenzuron, Dimefluthrin, Dimethoate, Dimethylvinphos, Dimpropyridaz, Dinotefuran, Diofenolan, Disulfoton, DNOC,d-T-80-phthalothrin (d-tetramethrin), emamectin benzoate, empenthrin, endosulfan, EPN, epsilon-metofluthrin, epsilon-momfluorothrin, esfenvalerate, ethiofencarb, ethiprole, etofenprox, etoxazole, etrimfos, Febantel, fenazaquin, fenbutatin oxide, fenitrothion, fenmezoditiaz, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyroximate, fenthion, fenvalerate, fipronil, flometoquin, flonicamid, fluacrypyrim, fluazuron, flubendiamide, fluchlorodiniliprole, flucycloxuron, flucythrinate, flufenerim, flufenoxuron, flufenprox, flufiprole, fluhexafon, flumethrin, flupentiofenox, flupyradifurone, flupyriminflupyroxystrobin, fluralaner, fluvalinate, fluxametamide, fonophos, formetanate, formothion, furathiocarb, gamma-cyhalothrin, halfenprox, halofenozide, heptafluthrin, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, imiprothrin, indazapyroxamet, indoxacarb, indoxacarb-MP, isocycloseram, isofenphos, isoprocarb, isoxathion, kappa-bifenthrin, kappa-tefluthrin, lambda-cyhalothrin, ledprona, lepimectin, lufenuron, malathion, meperfluthrin, metaflumizone, metalcarb, metaldehyde, methacrifos, methamidophos, methidathion, methomyl, methoprene, methoxychlor, methoxyfenozide, methyl bromide, metofluthrinMilbemectin, Momfluorothrin, Monocrotophos, Muscalure, Nicofluprole, Nitenpyram, Novaluron, Noviflumuron, Omethoate, Oxazosulfyl, Oxydemeton-methyl, Oxydeprofos, Parathion, Parathion-methyl, Pentachlorophenol, Permethrin, Phenothrin, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos-methyl, Praziquantel, Profenofos, Profluthrin, Propaphos, Propargite, Prothiofos, Protrifenbute, Pyflubumide, Pymetrozine, Pyraclofos, Pyrafluprole, Pyrethrins, Pyridaben, Pyridalyl, Pyrifluquinazon, Pyrimidifen, Pyriprole, Pyriproxyfen, Resmethrin, Rotenone, Silafluofen, Spidoxamat, Spinetoram,Spinosad, spirobudifen, spirodiclofen, spiromesifen, spiropidion, spirotetramat, spyromesifen, sulfiflumin, sulfotep, sulfoxaflor, sulprofos, tau-fluvalinate, tebufenozide, tebufenpyrad, teflubenzuron, tefluthorin, terbufos, tetrachlorantraniliprole, tetrachlorvinphos, tetramethrin, tetramethylfluthrin, tetraniliprole, thiacloprid, thiamethoxam, thiocyclam, thiodicarb, thiofanox, thiometon, tiorantraniliprole, tolfenpyrad, tralomethrin, transfluthrin, triazamate, triazuron, trichlorfon, triflumezopyrim, triflumuron, tyclopyrazoflor, vamidothion, zeta-cypermethrin, etc.

[0156] Fungicides: acibenzolar-S-methyl, acypetacs, aldimorph, allyl alcohol, ametoctradin, aminopyrifen, amisulbrom, amobam, ampropylfos, anilazine, azaconazole, azithiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentaluron, benthiavalicarb-isopropyl, benthiazole, benzamacril, benzamorf, benzovindiflupyr, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S, bordeaux mixture, boscalid, bromoconazole, bupirimate, buthiobate, butylamine, calcium polysulfide, captafol, captan, carbamorph, carbendazim, carboxin, carpropamid, carvone, cheshunt mixturemixture), chinomethionat, chlobenthiazone, chloraniformethane, chloranil, chlorfenazole, chloroneb, chloroinconazide, chloropicrin, chlorothalonil, chlorquinox, chlozolinate, climbazole, copper acetate, copper carbonate, basic, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper sulfate, copper sulfate, basic, copper zinc chromate, coumoxystrobin, cresol, cufraneb, cuprobam, cyazofamid, cyclafuramid, Cycloheximide, Cyflufenamid, Cymoxanil, Cypendazole, Cyproconazole, Cyprodinil, Cyprofuram, Dazomet, Debacarb, Decafentin, Dehydroacetic acid, Dichlobentiazox, Dichlofluanid, Dichlone, Dichlorophen, Dichlozoline, Diclobutrazol, Diclocymet, Diclomezine, Dichloran, Diethofencarb, Difenoconazole, Diflumetorim, Dimethirimol, Dimethomorph, Dimoxystrobin, Diniconazole, Diniconazole-M, Dinobuton, Dinocap, Dinocap-4, Dinocap-6, Dinocton, Dinosulfon, Dinoterbon, Diphenylamine, Dipymetitrone, Dipyrithione, Disulfiram, Ditalimfos, Dithianon, DNOC, Dodemorph, Dodine, Drazoxolon, Edifenphos, Enestrobin, EnoxastrobinEpoxiconazole, ethaboxam, etaconazole, etem, ethirimol, ethoxyquin, etridiazole, famoxadone, fenamidone, fenaminosulf, fenaminstrobin, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan, fenoxanil, fenpiclonil, fenpicoxamid, fenpropidin, fenpropimorph, fenpyrazamine, fentin, ferbam, ferimzone, florylpicoxamid, fluazinam, flubeneteram, fludioxonil, flufenoxadiazam, flufenoxystrobin, fluindapyr, flumetylsulforim, flumetover, flumorph, fluopicolide, fluopimomide, fluopyram, fluoroimide, fluotrimazole, fluoxapiprolin, fluoxastrobin, fluoxytioconazole, fluquinconazoleflusilazole, flusulfamide, flutolanil, flutianil, flutriafol, fluxapyroxad, folpet, fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbanil, furconazole, furconazole-cis, furmecyclox, furophanate, glyodin, griseofulvin, guazatine, halacrinate, hexachlorobenzene, hexaconazole, hexylthiofos, 8-hydroxyquinoline sulfate, hymexazol, imazalil, imibenconazole, iminoctadine-albesilate, iminoctadine-triacetate, inpyrfluxam, iodocarb, ipconazole, ipfentrifluconazole, ipflufenoquin, iprobenfos, iprodione, iprovalicarb, isofetamid, isoflucypram, isotianil, isoprothiolane, isopyrazam, isovaledioneKasugamycin, kresoxim-methyl, laminarin, mancopper, mancozeb, mandestrobin, mandipropamid, maneb, mebenil, mecarbinzid, mefentrifluconazole, mepanipyrim, mepronil, meptyldinocap, metalaxyl, metalaxyl-M, metam, metarylpicoxamid, metazoxolon, metconazole, methasulfocarb, methfuroxam, metyltetraprole, metiram, metominostrobin, metrafenone, metsulfovax, milneb, myclobutanil, myclozolin, nabam, naftifine, natamycin, nickel bis (dimethyldithiocarbamate), nitrostyrene, nitrothal-isopropyl, nuarimol, octhilinone, ofurace, orysastrobin, oxadixyl, oxathiapiprolin, oxine copper, oxpoconazole fumarate, oxycarboxinpefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, penthiopyrad, orthophenylphenol (2-phenylphenol), phosdiphen, phthalide, picarbutrazox, picoxystrobin, piperalin, polycarbamate, polyoxins, polyoxorim, potassium azide, potassium hydrogen carbonate, probenazole, prochloraz, procymidone, propamocarb hydrochloride, propiconazole, propineb, proquinazid, prothiocarb, pyrazophos, pyribencarb, pyrifenox, pyrimethanil, pyriminostrobin, pyroquilon, prothiocarb, prothioconazole, pydiflumetofen, pyracarbolid, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrapropoyne, pyraziflumid, pyridachlometyl, pyridinitril, pyriofenonepyrisoxazole, pyroxychlor, pyroxyfur, quinacetol-sulfate, quinazamid, quinconazole, quinoxyfen, quinofumelin, quintozene, rabenzazole, salicylanilide, seboctylamine, sedaxane, silthiofam, simeconazole, sodium hydrogen carbonate, sodium hypochlorite, spiroxamine, sulfur, tebuconazole, tebufloquin, tecloftalam, tecnazene, tecoram, tetraconazole, thiabendazole, thiadifluor, thicyofen, thifluzamide, thiochlorfenphim, thiophanate, thiophanate-methyl, thiram, tiadinil, tioxymid, tolclofos-methyl, tolprocarb, tolylfluanid, triadimefon, triadimenol, triamiphos, triarimol, triazbutil, triazoxide, tributyltin oxideTrichlamide, triclopyricarb, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, valifenalate, vinclozolin, zarilamid, zinc naphthenate, zinc sulfate, zineb, ziram, zoxamide, shiitake mycelium extract, shiitake fruiting body extract, etc.

[0157] Nematicides: aldoxycarb, benclothiaz, cadusafos, cyclobutrifluram, DBCP, dichlofenthion, DSP, ethoprophos, fenamiphos, fensulfothion, fluazaindolizine, fluensulfone, fosthiazate, fosthietan, imicyafos, isamidofos, isazofos, oxamyl, thionazin, tioxazafen, trifluenfuronate, etc.

[0158] Antiparasitic drugs: esfenvalerate, fenpropathrin, fenvalerate, cypermethrin, bifenthrin, cypermethrin, deltamethrin, etofenprox, lambda-cyhalothrin, permethrin, tefluthrin, zeta-cypermethrin, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiamethoxam, chromafenozide, fenoxycarb, lufenuron, methoprene, pyriproxyfen, triflumuron, chlorpyrifos, chlorpyrifos-methyl, diazinon, dichlorvos, fenitrothion, fenthion, malathion, pirimiphos-methyl, tetrachlorvinphos, ethiprole, fipronil, propoxur, carbaryl, bendiocarb, metoxadiazone, fenobucarb, carbofuran, afoxolaner, fluralaner, fluxametamide, sarolaner, lotilaner,tigolaner, esafoxolaner, modoflaner, umifoxolaner, mivorilaner, avermectin, ivermectin, doramectin, eprinomectin, maduramycin, milbemycin, milbemycin oxime, moxidectin, selamectin, indoxacarb, amitraz, bistrifluron, spinosad, albendazole, atovaquone, bithionol, cambendazole, carnidazole, chloroquine, clazuril, clorsulon, closantel, coumaphos, dichlorophen, diethylcarbamazine, diminazene, dinitolmide, dithiazanine iodide, emodepside, epsiprantel, febantel, fenbendazole, flubendazole, glycalpyramide, imidocarb, levamisole, mebendazole, mebendazole, mefloquine hydrochloride, melarsamine hydrochlorideMetronidazole, metyridine, monepantel, morantel tartrate, niclosamide, oxantel pamoate, oxantel tartrate, oxibendazole, oxyclozanide, piperazine adipate, piperazine citrate, piperazine phosphate, praziquantel, pyrantel pamoate, rafoxanide, tetramisole hydrochloride, thiabendazole, triclabendazole, etc.

[0159] Antibiotics: amoxicillin, ampicillin, cefapirin, Cefazolin sodium, cefquinome, ceftiofur, penicillin, chlortetracycline, oxytetracycline, danofloxacin, difloxacin, oxolinic acid, enrofloxacin, florfenicol, lincomycin, lomefloxacin, marbofloxacin, miloxacin, mirosamycin, norfloxacin, ofloxacin, orbifloxacin, valnemulin, thiamphenicol, tiamulin fumarate, tilmicosin phosphate, acetylisovaleryltylosin, tylosin phosphate, tulathromycin, ketoconazole, miconazole nitrate, clavulanic acid, etc.

[0160] The compound of the present invention has excellent insecticidal and acaricidal activities against many agricultural pests, mites, internal or external parasites of mammals or birds, and can also exert a sufficient control effect against pests that have acquired resistance to existing insecticides. Furthermore, it has almost no adverse effects on mammals, fish and beneficial insects, has low residue and a light environmental load. Therefore, the present invention can provide a useful novel pest control agent.

[0161] Based on the above, the embodiments of the present invention relate to the following [1] to [5].

[0162] [1] Formula (1): [Chemical formula] [In the formula, Q represents Q-1, Q-2, Q-3, Q-4, Q-6, Q-8, Q-9, Q-10, Q-12a or Q-47a,

[0163] [Chemical formula] Z 1 represents a halogen atom, C 1 ~C 6 alkyl, halo(C 1 ~C 6 )alkyl, C 1 ~C 6 alkoxy or cyano, J represents J-1 or J-2, [Chemical formula] G represents G-1, G-2, G-3 or G-7, [Chemical formula] Z 2 represents a halogen atom, C 1 ~C 6 alkyl or halo(C 1 ~C 6 )alkyl, R 1 represents a hydrogen atom, a halogen atom or halo(C 1 ~C 6 )alkyl, R 3 represents a hydrogen atom, Y represents an oxygen atom or a sulfur atom, t2 represents an integer of 0, 1 or 2, t3 represents an integer of 0, 1, 2 or 3, t4 represents an integer of 0, 1, 2, 3 or 4, t5 represents an integer of 0, 1, 2, 3, 4 or 5. ] The condensed heterocyclic amide compound represented thereby or a salt thereof.

[0164] [2] Q represents Q-1, Q-2 or Q-3, Z 1 represents a halogen atom, G represents a hydrogen atom or G-3, Z 2 represents a halogen atom, Y represents an oxygen atom. The condensed heterocyclic amide compound or a salt thereof according to the above [1].

[0165] [3] A pest control agent containing, as an active ingredient, one or more selected from the condensed heterocyclic amide compounds and salts thereof according to any one of the above [1] and [2].

[0166] [4] An agricultural chemical containing, as an active ingredient, one or more selected from the condensed heterocyclic amide compounds and salts thereof according to any one of the above [1] and [2].

[0167] [5] A control agent for internal or external parasites of mammals or birds containing, as an active ingredient, one or more selected from the condensed heterocyclic amide compounds and salts thereof according to any one of the above [1] and [2]. [Examples]

[0168] Hereinafter, the present invention will be described in more detail by presenting synthesis examples and test examples of the compounds of the present invention as examples, but the present invention is not limited thereto.

[0169] The medium-pressure preparative liquid chromatography described in the synthesis example used a medium-pressure preparative apparatus manufactured by Yamazen Corporation; YFLC-Wprep (flow rate: 18 ml / min, column packed with 40-μm silica gel).

[0170] In addition, the chemical shift values of the proton nuclear magnetic resonance spectra (hereinafter referred to as 1 1H-NMR) described below were measured in deuterated chloroform solvent using Me 4 Si (tetramethylsilane) as a reference substance at 300 MHz (model: JNM-ECX300 or JNM-ECP300, manufactured by JEOL Ltd.) or 400 MHz (model: JNM-ECZ400S, manufactured by JEOL Ltd.). Incidentally, 1 the symbols in the chemical shift values of 1H-NMR represent the following meanings.

[0171] s: singlet, d: doublet, dd: double doublet, t: triplet, q: quartet, m: multiplet, brs: broad singlet

[0172] Synthesis Example 1: Synthesis of N-(5-fluoropyridin-2-yl)-5-(3-(2-fluoropyridin-4-yl)-1,2,4-oxadiazol-5-yl)-3,7-dioxo-2,3,6,7-tetrahydro-5H-oxazolo[3,2-a]pyridine-8-carboxamide (Compound No. 1-001 of the present invention) To a mixed solution of 300 mg of N-(5-fluoropyridin-2-yl)-6-(3-(2-fluoropyridin-4-yl)-1,2,4-oxadiazol-5-yl)-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide, 3.0 ml of dichloromethane, and 223 mg of 4-dimethylaminopyridine was added 120 mg of 2-bromoacetyl chloride, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 5 ml of 1 mol / l hydrochloric acid was added, 5 ml of chloroform was added for extraction, and the solvent was distilled off under reduced pressure. To the obtained residue were added 1 ml of ethanol and 1 ml of diisopropyl ether. The precipitated solid was collected by filtration to obtain 156 mg of the target product as a pale yellow solid. Melting point: 212~214 °C

[0173] The synthesis examples of the production intermediates of the compounds of the present invention used in Synthesis Example 1 are described below.

[0174] Intermediate Synthesis Example 1: Synthesis of N-(5-fluoropyridin-2-yl)-6-(3-(2-fluoropyridin-4-yl)-1,2,4-oxadiazol-5-yl)-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide Step 1: Synthesis of di-tert-butyl 5-((5-fluoropyridin-2-yl)carbamoyl)-4-hydroxy-6-oxo-3,6-dihydropyridine-1,2(2H)-dicarboxylate To a mixed solution of 18.3 g of di-tert-butyl 4-hydroxy-6-oxo-3,6-dihydropyridine-1,2(2H)-dicarboxylate and 60 ml of acetonitrile, 4.0 g of imidazole and 6.6 g of 1,1'-carbonyldiimidazole were added, and the mixture was stirred at 85°C for 30 minutes. After cooling to room temperature, 6.6 g of 5-fluoropyridin-2-amine was added, and the mixture was stirred for 18 hours. 350 ml of diisopropyl ether was added, and the mixture was stirred at 0°C for 1.5 hours, and the precipitated solid was collected by filtration. The obtained solid was washed with a mixed solution of acetonitrile:diisopropyl ether = 1:5 to obtain 26.3 g of the target product as a light red solid. Melting point: 152~154°C

[0175] Step 2: Synthesis of 5-((5-fluoropyridin-2-yl)carbamoyl)-4-hydroxy-6-oxo-1,2,3,6-tetrahydropyridine-2-carboxylic acid To a mixed solution of 15.4 g of di-tert-butyl 5-((5-fluoropyridin-2-yl)carbamoyl)-4-hydroxy-6-oxo-3,6-dihydropyridine-1,2(2H)-dicarboxylate and 70 ml of dichloromethane, 50 ml of trifluoroacetic acid was added, and the mixture was stirred at room temperature for 25 hours. 140 ml of toluene was added, and the solvent was distilled off under reduced pressure. 100 ml of toluene was added, and the solvent was distilled off under reduced pressure. 100 ml of toluene was added, and the solvent was distilled off under reduced pressure. 100 ml of chloroform was added, and the solid was collected by filtration. The obtained solid was washed with chloroform to obtain 14.6 g of the target product as a white solid. Melting point: 223~225 °C

[0176] Step 3: Synthesis of 6-(((2-fluoropyridine-4-carboximidoyl)oxy)carbonyl)-N-(5-fluoropyridin-2-yl)-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide To a mixed solution of 100 mg of 5-((5-fluoropyridin-2-yl)carbamoyl)-4-hydroxy-6-oxo-1,2,3,6-tetrahydropyridine-2-carboxylic acid, 55 mg of 2-fluoro-N-hydroxyisonicotinimidamide and 4 ml of N,N-dimethylformamide, 72 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 5 mg of 1-hydroxy-7-azabenzotriazole were added, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 12 ml of water and 1 ml of 1 mol / l hydrochloric acid were added, and the precipitated solid was collected by filtration. The obtained solid was washed with water to obtain 80 mg of the target product as a white solid. Melting point: 146~148 °C

[0177] Step 4: Synthesis of N-(5-fluoropyridin-2-yl)-6-(3-(2-fluoropyridin-4-yl)-1,2,4-oxadiazol-5-yl)-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide To a mixed solution of 50 mg of 6 - ((((2 - fluoroisonicotinimidoyl)oxy)carbonyl)-N-(5 - fluoropyridin - 2 - yl)-4 - hydroxy - 2 - oxo - 1,2,5,6 - tetrahydropyridine - 3 - carboxamide and 1.7 ml of toluene, 17 mg of triethylamine was added, and the mixture was stirred at 110 °C for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. To the obtained residue, 5 ml of 1 mol / l hydrochloric acid was added, and extraction was performed with ethyl acetate (5 ml × 3 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. To the obtained residue, 1 ml of N,N - dimethylformamide, 3 ml of water, and 1 ml of 1 mol / l hydrochloric acid were added. The precipitated solid was collected by filtration, and 39 mg of the target product was obtained as a white solid. Melting point: 159 - 161 °C

[0178] The compounds of the present invention can be synthesized according to the above production method and synthesis examples. Examples of the condensed heterocyclic amide compounds produced in the same manner as in Synthesis Example 1 are shown in Table 1 and Table 2, but the condensed heterocyclic amide compounds of the present invention are not limited thereto.

[0179] In addition, the descriptions of Q - 1, Q - 2, and Q - 3 in the table represent the following structures respectively.

[0180]

Chemical formula

[0181] Also, the description of G - 3 in the table represents the following structure.

[0182]

Chemical formula

[0183] In addition, the numbers described in the above structural formula represent the substitution positions of the substituents (Z 1 ) t4 or (Z 2 ) t4 For example, "Q - 3(4 - F)" in the table represents "5 - fluoropyridin - 2 - yl".

[0184] In addition, "m.p." represents the melting point (unit: °C).

[0185] [Table 1]

[0186] [Chemistry]

[0187] ―――――――――――――――――――――― No. Q G m.p.(°C) ―――――――――――――――――――――― 1-001 Q-3(4-F) G-3(3-F) 212-214 1-002 Q-2(4-F) G-3(3-F) 236-238 ―――――――――――――――――――――― [Table 2]

[0188] [Chemistry]

[0189] ――――――――――――――――――――――― No. Q G R 1 m.p.(°C) ――――――――――――――――――――――― 2-001 Q-1(4-F) H CF 3 186-188 ――――――――――――――――――――――― [Test Example] Next, the usefulness of the compound of the present invention as a pest control agent will be specifically described in the following test examples, but the present invention is not limited thereto.

[0190] Test Example 1: Insecticidal Test against the Green Rice Leafhopper A 10% by mass emulsion of the compound of the present invention prepared according to the above formulation example of the emulsion was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. The leaf sheaths of rice were immersed in the chemical solution for about 10 seconds. After the immersion operation was completed, the leaf sheaths of the rice treated with the chemical solution were air-dried and then placed in a test tube. Five third-instar larvae of the brown planthopper (Nilaparvata lugens) were released into each test tube, covered with a sponge, and placed in a constant temperature room at 25°C. Six days after the placement, the number of dead insects of the brown planthopper in the test tube was investigated, and the mortality rate was calculated from the following formula. The test was conducted in duplicate.

[0191] Mortality rate (%) = (Number of dead insects / Number of test insects) × 100 As a result, the following compounds showed a mortality rate of 90% or more.

[0192] Compounds of the present invention: 1-001, 1-002, 2-001 Test Example 2: Insecticidal test against the green peach aphid Wet absorbent cotton was placed in a glass petri dish with an inner diameter of 3 cm, and a leaf of Cymbidium cut into a circle with a diameter of 3 cm was placed on it. Four wingless adult green peach aphids (Myzus persicae) were released. One day later, a 10% by mass emulsion of the compound of the present invention prepared according to the above formulation example of the emulsion was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. The prepared chemical solution was sprayed in a rotary spraying tower (2.5 mg / cm 2 ) and covered and placed in a constant temperature room at 25°C. Six days after the placement, the number of dead insects of the green peach aphid in the petri dish was investigated, and the mortality rate was calculated from the same formula as in Test Example 1. The test was conducted in duplicate.

[0193] As a result, the following compounds showed a mortality rate of 90% or more.

[0194] Compounds of the present invention: 1-001, 2-001 Test Example 3: Insecticidal activity against the citrus red mite A wet filter paper was laid in a Styrofoam cup with an inner diameter of 7 cm, and kidney bean leaves cut into 3 cm squares were placed thereon. Twenty larvae of Frankliniella occidentalis were inoculated per leaf. A 10% by mass emulsion of the compound of the present invention prepared according to the above formulation example of the emulsion was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. The prepared chemical solution was sprayed at 2.5 ml per Styrofoam cup using a rotary spraying tower (2.5 mg / cm 2 ). Two days later, the number of dead Frankliniella occidentalis in the Styrofoam cup was investigated, and the mortality rate was calculated from the same calculation formula as in Test Example 1. The test was conducted in duplicate.

[0195] As a result, the following compounds showed a mortality rate of 90% or more.

[0196] Compound of the present invention: 1-001, 1-002, 2-001 Test Example 4: Insecticidal test against Plutella xylostella A 10% by mass emulsion of the compound of the present invention prepared according to the above formulation example of the emulsion was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. Chinese cymbidium leaves were immersed in the chemical solution for about 10 seconds. After the immersion operation was completed, the Chinese cymbidium leaves treated with the chemical solution were air-dried and then placed in a petri dish. Five third-instar larvae of Plutella xylostella were released per petri dish, covered, and placed in a constant temperature room at 25°C. Six days after placement, the number of dead Plutella xylostella in the petri dish was investigated, and the mortality rate was calculated from the same calculation formula as in Test Example 1. The test was conducted in duplicate.

[0197] As a result, the following compounds showed a mortality rate of 90% or more.

[0198] Compound of the present invention: 1-001, 1-002, 2-001

Industrial Applicability

[0199] The condensed heterocyclic amide compound of the present invention or a salt thereof has excellent pest control activity and can be used as a pest control agent.

Claims

1. Formula (1): 【Chemistry 1】 [In the formula, Q represents Q-1, Q-2, Q-3, Q-4, Q-6, Q-8, Q-9, Q-10, Q-12a or Q-47a, 【Chemistry 2】 Z １ is a halogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) Alkyl, C １ ~C ６ represents alkoxy or cyano; J represents J-1 or J-2; 【Chemistry 3】 G represents G-1, G-2, G-3 or G-7; 【Chemistry 4】 Z ２ is a halogen atom, C １ ~C ６ Alkyl or halo(C １ ~C ６ ) alkyl; R 1 is a hydrogen atom, a halogen atom or a halo(C １ ~C ６ ) alkyl; R ３ represents a hydrogen atom, Y represents an oxygen atom or a sulfur atom; t2 represents an integer of 0, 1 or 2; t3 represents an integer of 0, 1, 2 or 3; t4 represents an integer of 0, 1, 2, 3 or 4; and t5 represents an integer of 0, 1, 2, 3, 4 or 5.] or a salt thereof.

2. Q represents Q-1, Q-2 or Q-3; Z １ represents a halogen atom, G represents a hydrogen atom or G-3; Z ２ represents a halogen atom, The fused heterocyclic amide compound or a salt thereof according to claim 1 , wherein Y represents an oxygen atom.

3. A pest control agent comprising, as an active ingredient, one or more selected from the fused heterocyclic amide compounds and salts thereof according to claim 1 or 2.

4. 3. An agricultural chemical comprising, as an active ingredient, one or more selected from the fused heterocyclic amide compounds and salts thereof according to claim 1 or 2.

5. 3. An agent for controlling internal or external parasites of mammals or birds, comprising as an active ingredient one or more selected from the fused heterocyclic amide compounds and salts thereof according to claim 1 or 2.

Images