Amide compound and method for controlling cockroaches

Abstract

A method for controlling cockroaches comprising a step for applying a compound represented by formula (I): (wherein X1 represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; X2 represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; and X3 represents a hydrogen atom, a fluorine atom, or a chlorine atom), an N-oxide thereof, or a salt or solvate thereof to cockroaches or a habitat thereof, or a place where appearance thereof is predicted.

Description

Amide compounds and methods for controlling cockroaches

[0001] This application claims priority and benefits of Japanese Patent Application No. 2025-031396, filed on 28 February 2025, the entire contents of which are incorporated herein by reference. The present invention relates to amide compounds and methods for controlling cockroaches.

[0002] Patent Document 1 describes an amide compound.

[0003] International Publication No. 2003 / 015518

[0004] The objective of this invention is to provide an excellent method for controlling cockroaches.

[0005] The inventors of this invention, in an effort to find an excellent method for controlling cockroaches, have found that the compound represented by the following formula (I) has excellent control efficacy against cockroaches.

[0006] The present invention includes the following [1] to

[14] : [1] Formula (I): (In formula (I), X 1 X represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. 2 X represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. 3A method for controlling cockroaches (hereinafter sometimes referred to as the "method of the present invention"), comprising the step of applying a compound represented by ) (where represents a hydrogen atom, a fluorine atom, or a chlorine atom), its N oxide, a salt thereof, or a solvate thereof (hereinafter referred to as the "compound") to a cockroach, its habitat, or a place where its appearance is predicted. [2] The method for controlling cockroaches according to [1], wherein the cockroach belongs to the order Blattodea, excluding the suborder Termites. [3] The method for controlling cockroaches according to [1], wherein the cockroach belongs to the genus Blattella or the genus Periplaneta. [4] The method for controlling cockroaches according to [1], wherein the cockroach is Blattella germanica. [5] The method for controlling cockroaches according to [1], wherein the cockroach is Periplaneta americana. [6] The application rate of the compound represented by formula (I), its N oxide, their salts, or their solvates is 0.1 to 160 mg / m². 2The method of control according to any one of [1] to [5]. [7] The method of control according to any one of [1] to [6], wherein a composition comprising a compound represented by formula (I), its N oxide, a salt thereof, or a solvate thereof, selected from the group consisting of a surfactant and an inert carrier, is applied to cockroaches, their habitat, or a place where their appearance is expected. [8] The method of control according to any one of [1] to [6], wherein a compound represented by formula (I), its N oxide, a salt thereof, or a solvate thereof is applied as a bait containing a food component to a place where cockroaches live or where their appearance is expected. [9] The method of control according to [8], wherein a compound represented by formula (I), its N oxide, a salt thereof, or a solvate thereof is applied as a bait containing a food component to a place where cockroaches live or where their appearance is expected, thereby causing cockroaches to orally ingest the compound represented by formula (I), its N oxide, a salt thereof, or a solvate thereof.

[10] A method of controlling cockroaches according to any one of [1] to [6], wherein a composition comprising a compound represented by formula (I), its N oxide, a salt thereof, or a solvate thereof, selected from the group consisting of a surfactant and an inert carrier, is applied to a place where cockroaches live or where their appearance is expected.

[11] A method of controlling cockroaches according to

[10] , wherein a composition comprising a compound represented by formula (I), its N oxide, a salt thereof, or a solvate thereof, selected from the group consisting of a surfactant and an inert carrier, is applied to a place where cockroaches live or where their appearance is expected, thereby bringing the compound represented by formula (I), its N oxide, a salt thereof, or a solvate thereof remaining at the applied location into contact with cockroaches.

[12] A method of controlling cockroaches according to

[10] or

[11] , wherein the cockroach control effect is maintained for three months after application of the compound represented by formula (I), its N oxide, a salt thereof, or a solvate thereof.

[13] Formula (II): (In formula (II), X 1a X represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. 1a However, if it is a fluorine atom, X 2a and X 3aa combination with X 2a is an iodine atom, and X 3a is a fluorine atom; X 2a is a chlorine atom, and X 3a is a hydrogen atom; or X 2a is an iodine atom, and X 3a is a chlorine atom, and when X 1a is a chlorine atom, X 2a represents an iodine atom, and X 3a represents a fluorine atom, and when X 1a is a bromine atom, X 2a represents an iodine atom, and X 3a represents a hydrogen atom, a fluorine atom, or a chlorine atom, and when X 1a is an iodine atom, X 2a represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and X 3a represents a hydrogen atom, a fluorine atom, or a chlorine atom.), an N-oxide thereof, a salt thereof or a solvate thereof (hereinafter referred to as the compound of the present invention).

[14] A composition comprising the compound according to

[13] , an N-oxide thereof, a salt thereof or a solvate thereof, and an inert carrier.

[0007] According to the present invention, cockroaches can be controlled.

[0008] The present compound used in the method of the present invention is described below.

[0009] The present compound used in the method of the present invention is a compound represented by formula (I): (wherein, X 1 represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, X 2 represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, X 3 represents a hydrogen atom, a fluorine atom, or a chlorine atom.), an N-oxide thereof, a salt thereof or a solvate thereof. Examples of the present compound (including the compound of the present invention) include the following compounds. Formula (I): In the compound represented by , X 1 , X 2and X 3 A compound whose combination is one of the combinations listed in Table 1. Hereinafter, the compounds listed in Table 1 will be referred to as Compound 1 to 48, respectively.

[0010]

[0011] Examples of these compounds include the N oxides of compounds 1 to 48, their salts, or their solvates.

[0012] The following are examples of embodiments of the compound used in the method of the present invention: (Embodiment 1) In the compound represented by formula (I), X 1 However, a compound in which X is a chlorine atom, a bromine atom, or an iodine atom. (Aspect 2) In the compound represented by formula (I) above, X 1 A compound in which X is a fluorine atom, a bromine atom, or an iodine atom. (Aspect 3) In the compound represented by formula (I), X 1 However, a compound in which the atom is a fluorine atom, a chlorine atom, or an iodine atom. (Aspect 4) In the compound represented by formula (I), X 1 A compound in which X is a fluorine atom, a chlorine atom, or a bromine atom. (Aspect 5) In the compound represented by formula (I), X 1 However, a compound in which the atom is a bromine atom or an iodine atom. (Aspect 6) In the compound represented by formula (I) above, X 1 However, a compound in which the atom is a chlorine atom or an iodine atom. (Aspect 7) In the compound represented by formula (I), X 1 However, a compound in which the atom is a chlorine atom or a bromine atom. (Aspect 8) In the compound represented by formula (I), X 1 However, a compound in which the atom is a fluorine atom or an iodine atom. (Aspect 9) In the compound represented by formula (I), X 1 However, a compound in which the atom is a fluorine atom or a bromine atom. (Aspect 10) In the compound represented by formula (I), X 1 A compound in which X is a fluorine atom or a chlorine atom. (Aspect 11) In the compound represented by formula (I), X 1 However, a compound in which the atom is a fluorine atom. (Aspect 12) In the compound represented by formula (I), X 1However, a compound in which the atom is a chlorine atom. (Aspect 13) In the compound represented by formula (I), X 1 However, a compound in which the atom is bromine. (Aspect 14) In the compound represented by formula (I), X 1 However, a compound in which the atom is an iodine atom. (Aspects 15-28) In any of aspects 1-14, X 2 A compound in which X is a chlorine atom, a bromine atom, or an iodine atom. (Aspects 29-42) In any of aspects 1-14, X 2 A compound in which the atom is a fluorine atom, a bromine atom, or an iodine atom. (Aspects 43 to 56) In any of aspects 1 to 14, X 2 A compound in which X is a fluorine atom, a chlorine atom, or an iodine atom. (Aspects 57-70) In any of aspects 1-14, X 2 A compound in which X is a fluorine atom, a chlorine atom, or a bromine atom. (Aspects 71 to 84) In any of aspects 1 to 14, X 2 A compound in which X is a bromine atom or an iodine atom. (Aspects 85-98) In any of aspects 1-14, X 2 A compound in which X is a chlorine atom or an iodine atom. (Aspects 99 to 112) In any of aspects 1 to 14, X 2 However, a compound which is a chlorine atom or a bromine atom. (Aspects 113 to 126) In any of aspects 1 to 14, X 2 A compound in which the atom is either a fluorine atom or an iodine atom. (Aspects 127-140) In any of aspects 1-14, X 2 However, a compound which is a fluorine atom or a bromine atom. (Aspects 141 to 154) In any of aspects 1 to 14, X 2 However, a compound which is a fluorine atom or a chlorine atom. (Aspects 155-168) In any of aspects 1 to 14, X 2 However, a compound in which the atom is a fluorine atom. (Aspects 169-182) In any of aspects 1 to 14, X 2 However, a compound in which the atom is a chlorine atom. (Aspects 183-196) In any of aspects 1 to 14, X 2 However, a compound in which the atom is bromine. (Aspects 197-210) In any of aspects 1 to 14, X 2 However, a compound in which the atom is an iodine atom. (Aspects 211 to 420) In any of aspects 1 to 210, X3 However, a compound which is a fluorine atom or a chlorine atom. (Aspects 421 to 630) In any of aspects 1 to 210, X 3 A compound in which the atom is a hydrogen atom or a chlorine atom. (Aspects 631 to 840) In any of aspects 1 to 210, X 3 A compound in which the atom is a hydrogen atom or a fluorine atom. (Aspects 841 to 1050) In any of aspects 1 to 210, X 3 However, a compound in which the atom is a hydrogen atom. (Aspects 1051 to 1260) In any of aspects 1 to 210, X 3 However, a compound in which the atom is a fluorine atom. (Aspects 1261 to 1470) In any of aspects 1 to 210, X 3 However, it is a compound that contains a chlorine atom.

[0013] Examples of the compound of the present invention are as follows: (Aspect A1) In the compound represented by formula (II), X 1a However, a compound in which the atom is a fluorine atom. (Aspect A2) In aspect A1, X 2a and X 3a The combination with X 2a X is an iodine atom. 3a A combination in which is a fluorine atom, or X 2a X is a chlorine atom 3a A compound in which X is a hydrogen atom. (Aspect A3) In Aspect A1, X 2a and X 3a The combination with X 2a X is an iodine atom. 3a A combination in which is a fluorine atom, or X 2a X is an iodine atom. 3a A compound in which X is a chlorine atom. (Aspect A4) In Aspect A1, X 2a and X 3a The combination with X 2a X is a chlorine atom 3a A combination in which is a hydrogen atom, or X 2a X is an iodine atom. 3a A compound in which X is a chlorine atom. (Aspect A5) In Aspect A1, X 2a and X 3a The combination with X 2a X is an iodine atom.3a A compound which is a combination wherein is a fluorine atom. (Aspect A6) In Aspect A1, X 2a and X 3a the combination with is X 2a is a chlorine atom and X 3a A compound which is a combination wherein is a hydrogen atom. (Aspect A7) In Aspect A1, X 2a and X 3a the combination with is X 2a is an iodine atom and X 3a A compound which is a combination wherein is a chlorine atom. (Aspect A8) In the compound represented by formula (II), X 1a A compound wherein is a chlorine atom. (Aspect A9) In the compound represented by formula (II), X 1a A compound wherein is a bromine atom. (Aspect A10) In Aspect A9, X 3a A compound wherein is a fluorine atom or a chlorine atom. (Aspect A11) In Aspect A9, X 3a A compound wherein is a hydrogen atom or a chlorine atom. (Aspect A12) In Aspect A9, X 3a A compound wherein is a hydrogen atom or a fluorine atom. (Aspect A13) In Aspect A9, X 3a A compound wherein is a hydrogen atom. (Aspect A14) In Aspect A9, X 3a A compound wherein is a fluorine atom. (Aspect A15) In Aspect A9, X 3a A compound wherein is chlorine. (Aspect A16) In the compound represented by formula (II), X 1a A compound wherein is an iodine atom. (Aspect A17) In Aspect A16, X 2a A compound wherein is a chlorine atom, a bromine atom, or an iodine atom. (Aspect A18) In Aspect A16, X 2a A compound wherein is a fluorine atom, a bromine atom, or an iodine atom. (Aspect A19) In Aspect A16, X 2a A compound wherein is a fluorine atom, a chlorine atom, or an iodine atom. (Aspect A20) In Aspect A16, X 2a A compound wherein is a fluorine atom, a chlorine atom, or a bromine atom. (Aspect A21) In Aspect A16, X 2a A compound wherein is a bromine atom or an iodine atom. (Aspect A22) In Aspect A16, X2a However, a compound which is a chlorine atom or an iodine atom. (Aspect A23) In Aspect A16, X 2a However, a compound which is a chlorine atom or a bromine atom. (Aspect A24) In Aspect A16, X 2a However, a compound which is a fluorine atom or an iodine atom. (Aspect A25) In Aspect A16, X 2a However, a compound which is a fluorine atom or a bromine atom. (Aspect A26) In Aspect A16, X 2a However, a compound which is a fluorine atom or a chlorine atom. (Aspect A27) In Aspect A16, X 2a However, a compound that is a fluorine atom. (Aspect A28) In Aspect A16, X 2a However, a compound that is a chlorine atom. (Aspect A29) In Aspect A16, X 2a However, a compound in which the atom is bromine. (Aspect A30) In Aspect A16, X 2a However, a compound in which the atom is iodine. (Aspects A31 to A45) In any of aspects A16 to A30, X 3a However, a compound which is a fluorine atom or a chlorine atom. (Aspects A46 to A60) In any of aspects A16 to A30, X 3a However, a compound which is a hydrogen atom or a chlorine atom. (Aspects A61 to A75) In any of aspects A16 to A30, X 3a A compound in which the atom is a hydrogen atom or a fluorine atom. (Aspects A76 to A90) In any of aspects A16 to A30, X 3a However, a compound in which the atom is a hydrogen atom. (Aspects A91 to A105) In any of aspects A16 to A30, X 3a However, a compound in which the atom is a fluorine atom. (Aspects A106 to A120) In any of aspects A16 to A30, X 3a However, it is a compound that contains a chlorine atom.

[0014] Next, a method for producing the present compound (including the compound of the present invention) will be described.

[0015] Manufacturing Method 1 The compound represented by formula (I) (hereinafter referred to as compound (I)) can be produced by reacting the compound represented by formula (M-1) (hereinafter referred to as compound (M-1)) with ammonia or its equivalent. [In the formula, X1 X represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. 2 X represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. 3 ∫ represents a hydrogen atom, a fluorine atom, or a chlorine atom. The reaction is carried out in or without a solvent. Examples of solvents include ethers such as tetrahydrofuran (hereinafter referred to as THF), 1,4-dioxane, 1,2-dimethoxyethane (hereinafter referred to as DME), methyl tert-butyl ether (hereinafter referred to as MTBE), and diethyl ether (hereinafter referred to as ethers); halogenated hydrocarbons such as dichloromethane and chloroform (hereinafter referred to as halogenated hydrocarbons); alcohols such as methanol, ethanol, and isopropanol (hereinafter referred to as alcohols); nitriles such as acetonitrile (hereinafter referred to as nitriles); ketones such as acetone and methyl isobutyl ketone (hereinafter referred to as ketones); and mixtures thereof. Examples of ammonia or its equivalent include ammonia water (typically a 28% aqueous solution) or an ammonia-ethanol solution. In the reaction, ammonia or its equivalent is usually used in a ratio of 1 to 10 moles per mole of compound (M-1). The reaction temperature is typically in the range of -30 to 120°C. The reaction time is typically in the range of 0.1 to 24 hours. After the reaction is complete, compound (I) can be obtained by post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, drying the organic layer, and concentrating it.

[0016] As for compound (M-1), X is in formula (M-1). 1 , X 2 and X 3 Examples of compounds whose combinations are any of those listed in Table 2 below are given, and these are referred to as intermediates 1 to 48, respectively.

[0017]

[0018] Manufacturing Method 2 Compound (I) can be produced by reacting the compound represented by formula (M-2) (hereinafter referred to as compound (M-2)) with the compound represented by formula (R-1) (hereinafter referred to as compound (R-1)) in the presence of an alkyl sulfonyl chloride and a base. [In the formula, X 1 X represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. 2 X represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. 3 ∫ represents a hydrogen atom, a fluorine atom, or a chlorine atom. The reaction is usually carried out in a solvent. Examples of solvents include ethers, halogenated hydrocarbons, nitriles, ketones, and mixtures thereof. Examples of alkylsulfonyl chlorides include methanesulfonyl chloride, ethylsulfonyl chloride, and propylsulfonyl chloride. Examples of bases include triethylamine, diisopropylethylamine, pyridine, and 3-methylpyridine. In the reaction, compound (R-1) is usually used in a ratio of 1 to 3 moles, alkylsulfonyl chloride in a ratio of 1 to 4 moles, and base in a ratio of 1 to 4 moles per mole of compound (M-2). The reaction temperature is usually in the range of 0 to 120°C. The reaction time is usually in the range of 0.5 to 24 hours. After the reaction is complete, compound (I) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, drying the organic layer, and concentrating it. Compound (R-1) may be a commercially available compound or can be produced using known methods (e.g., the method described in WO2003016283).

[0019] Reference Manufacturing Method 1 Compound (M-1) can be produced by reacting compound (R-1) with compound (R-1) represented by formula (R-2) (hereinafter referred to as compound (R-2)) in the presence of an alkyl sulfonyl chloride and a base. [In the formula, X 1 X represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. 2 X represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. 3∫ represents a hydrogen atom, a fluorine atom, or a chlorine atom. The reaction is usually carried out in a solvent. Examples of solvents include ethers, halogenated hydrocarbons, ketones, and mixtures thereof. Examples of alkylsulfonyl chlorides include methanesulfonyl chloride, ethylsulfonyl chloride, and propylsulfonyl chloride. Examples of bases include triethylamine, diisopropylethylamine, and pyridine. In the reaction, compound (R-1) is usually used in a ratio of 1 to 3 moles, alkylsulfonyl chloride in a ratio of 2 to 4 moles, and base in a ratio of 2 to 5 moles per mole of compound (R-2). The reaction temperature is usually in the range of 0 to 120°C. The reaction time is usually in the range of 0.5 to 24 hours. After the reaction is complete, compound (M-1) can be obtained by adding water to the reaction mixture, filtering out the precipitate, washing with water and an organic solvent, and drying. Compound (R-2) may be a commercially available compound or can be produced using known methods (e.g., the method described in CN110835308).

[0020] Reference Manufacturing Method 2 Compound (M-2) can be manufactured according to the following scheme. [In the formula, X 1 X represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. 2 X represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. 3 This represents a hydrogen atom, a fluorine atom, or a chlorine atom.

[0021] The compound represented by formula (M-3) (hereinafter referred to as compound (M-3)) can be produced by reacting compound (R-2) with a carbonylating agent. The reaction is usually carried out in a solvent. Examples of solvents include ethers, halogenated hydrocarbons, hydrocarbons, and mixtures thereof. Examples of carbonylating agents include phosgene, triphosgene, dimethyl carbonate, and carbonyldiimidazole (hereinafter referred to as CDI). A base may be used in the reaction as needed. Examples of bases include organic bases; alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter referred to as alkali metal carbonates); and alkali metal hydrides such as sodium hydride (hereinafter referred to as alkali metal hydrides). In the reaction, the carbonylating agent is usually used in a ratio of 1 to 2 moles per mole of compound (R-2). When a base is used in the reaction, the base is usually used in a ratio of 2 to 4 moles per mole of compound (R-2). The reaction temperature is typically in the range of 0 to 120°C. The reaction time is typically in the range of 0.5 to 24 hours. After the reaction is complete, compound (M-3) can be obtained by post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, drying the organic layer, and concentrating it.

[0022] Compound (M-2) can be produced by reacting compound (M-3) with ammonia or its equivalent. Specifically, compound (M-2) can be produced in the same manner as in production method 1, except that compound (M-3) is used instead of compound (M-1).

[0023] In the method of the present invention, the compound may be mixed with or used in combination with other insecticidal active ingredients. Mixing or using in combination means using the compound and the other insecticidal active ingredients simultaneously, separately, or at time intervals. When the compound and the other insecticidal active ingredients are used simultaneously, the compound and the other insecticidal active ingredients may be contained in separate formulations or in a single formulation.

[0024] This compound can be used to control cockroaches. Cockroaches that can be controlled by this compound include arthropods belonging to the order Blattodea, excluding the suborder Termites. Specifically, examples include the following: Ectobiidae species such as the German cockroach (Blattella germanica), Okinawa cockroach (Blattella asahinai), and brown-banded cockroach (Supella longipalpa); and Blattidae species such as the American cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta americana), small American cockroach (Periplaneta australasiae), brown cockroach (Periplaneta brunnea), Eastern cockroach (Blatta orientalis), and Turkestan cockroach (Blatta lateralis). In one embodiment of the present invention, the compound can suitably control cockroaches belonging to the genus Blattella or the genus Periplaneta. Examples of cockroaches belonging to the genus Blattella include the German cockroach (Blattella germanica) and the Okinawa cockroach (Blattella asahinai). Examples of cockroaches belonging to the genus Periplaneta include the American cockroach (Periplaneta fuliginosa), the American cockroach (Periplaneta americana), the small American cockroach (Periplaneta australasiae), and the brown cockroach (Periplaneta brunnea).

[0025] The cockroaches controlled by the method of the present invention include cockroaches that have developed reduced sensitivity (or resistance) to certain insecticides. Specifically, examples include the following: German cockroaches with reduced sensitivity to acetylcholinesterase inhibitors; German cockroaches with reduced sensitivity to GABAergic chloride channel blockers; German cockroaches with reduced sensitivity to sodium channel modulators; German cockroaches with reduced sensitivity to nicotinic acetylcholine receptor competitive modulators; German cockroaches with reduced sensitivity to glutamatergic chloride channel allosteric modulators; German cockroaches with reduced sensitivity to chlorpyrifos, malathion, propoxul, fipronil, beta-cyfluthrin, cypermethrin, deltamethrin, permethrin, pyrethrin, DDT, imidacloprid, clothianidin, indoxacarb, and / or abamectin; German cockroaches with D58G, E434K, C764R, L933F, and / or P1880L amino acid substitutions in voltage-gated sodium channels; German cockroaches with the A302S amino acid substitution in their GABAergic chloride ion channels; German cockroaches overexpressing CYP4G19 (a type of cytochrome P450 gene).

[0026] The method of the present invention can effectively control cockroaches at any stage of development. Specifically, it can control cockroaches at any stage of development, whether they are juvenile, middle-aged, elderly, or adult.

[0027] The present invention's method includes the step of applying the compound to cockroaches, their habitats, or places where their appearance is predicted.

[0028] Specific application methods include, for example, when applied to buildings, treatment of the walls, floors, underfloors, ceilings, roofs, attics, doors, windows, screens, etc., treatment of the indoor space of the building, and installation of poison bait or resin formulations. When applied outdoors, treatment of the ground, exterior walls, fences, and ditches, soil injection into underfloors and the ground, treatment of spaces, and treatment of granular or resin formulations in water.

[0029] In the method of the present invention, the amount of compound applied is preferably 0.1 to 160 mg / m² as the mass of the compound per treatment area. 2 For example, the specific dosage of this compound is 0.2 mg / m². 2 , 0.3 mg / m² 2 , 0.4 mg / m² 2 , 0.5 mg / m² 2 , 0.6 mg / m² 2 , 0.7 mg / m² 2 , 0.8 mg / m² 2 , 0.9 mg / m² 2 , 1 mg / m² 2 , 2 mg / m 2 , 3 mg / m² 2 , 4 mg / m² 2 , 5 mg / m² 2 , 6 mg / m² 2 7 mg / m² 2 , 8 mg / m² 2 9 mg / m² 2 , 10 mg / m² 2 , 15 mg / m² 2 , 20 mg / m² 2 , 25 mg / m² 2 , 30 mg / m² 2 , 35 mg / m² 2 , 40 mg / m² 2 , 45 mg / m² 2 50 mg / m² 2 , 55 mg / m² 2 60 mg / m² 2 , 65 mg / m² 2 70 mg / m² 2 75 mg / m² 2 , 80 mg / m² 2 , 85 mg / m² 2 90 mg / m² 2 95 mg / m² 2 , 100 mg / m² 2 , 110 mg / m² 2 , 120 mg / m² 2 , 130 mg / m² 2 , 140 mg / m² 2 , 150 mg / m² 2 These are some examples. These dosages can also be expressed as "approximately." "Approximately" means plus or minus 10%, for example, "approximately 1 mg / m²." 2This refers to 0.9 to 1.1 mg / m³ 2 That is the case.

[0030] In the present invention, the compound is prepared by mixing an inert carrier such as a solid carrier, liquid carrier, or gaseous carrier with a surfactant, etc., and adding, as necessary, formulation aids such as a thickener, protective colloidal agent, antifreeze, defoaming agent, antifungal agent, preservative / bactericidal agent, antioxidant, light stabilizer, pH adjuster, binder, adhesive / spreading agent, lubricant / smoothener, anticaking agent, fragrance, coating agent, inclusion agent, etc., to produce liquid formulations (soluble concentrate), aqueous suspension concentrate, oil-based suspension concentrate, oil miscible liquid, emulsifiable concentrate, emulsion (emulsion in water), suspoemulsion, microemulsion, microcapsule suspension, wettable powder, water-soluble powder, water dispersible granule, water-soluble powder. It can be formulated and used in the form of granules, dustable powders, tablets, emulsifiable gels, aerosols, resin formulations, baits, etc. However, it can also be formulated and used in the dosage forms described in the Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers-271 to 276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2016, ISSN:0259-2517.In one embodiment of the present invention, it is preferable to formulate the compound into any of the following: aqueous suspension, microcapsules, granular wettable powder, granular aqueous soluble powder, wettable powder, emulsion, or emulsion.

[0031] When this compound is formulated and used, the amount of this compound contained in the formulation is usually 0.0001 to 99% by weight, preferably 0.01 to 90% by weight, and more preferably 0.01 to 50% by weight. The specific amounts of this compound are 0.02% by weight, 0.03% by weight, 0.04% by weight, 0.05% by weight, 0.06% by weight, 0.07% by weight, 0.08% by weight, 0.09% by weight, 0.1% by weight, 0.2% by weight, 0.3% by weight, 0.4% by weight, 0.5% by weight, 0.6% by weight, 0.7% by weight, 0.8% by weight, 0.9% by weight, 1% by weight, 2% by weight, 3% by weight, 4% by weight, 5% by weight, 6% by weight, 7% by weight, 8% by weight, 9% by weight, 10% by weight, 11% by weight, 12% by weight, 13% by weight, 14% by weight, 15% by weight, 16% by weight, 17% by weight, 18% by weight, 19% by weight, 20% by weight, 21% by weight, 22% by weight, 2 Examples include 3% by weight, 24% by weight, 25% by weight, 26% by weight, 27% by weight, 28% by weight, 29% by weight, 30% by weight, 31% by weight, 32% by weight, 33% by weight, 34% by weight, 35% by weight, 36% by weight, 37% by weight, 38% by weight, 39% by weight, 40% by weight, 41% by weight, 42% by weight, 43% by weight, 44% by weight, 45% by weight, 46% by weight, 47% by weight, 48% by weight, 49% by weight, 50% by weight, 51% by weight, 52% by weight, 53% by weight, 54% by weight, 55% by weight, 56% by weight, 57% by weight, 58% by weight, 59% by weight, 60% by weight, 65% by weight, 70% by weight, 75% by weight, 80% by weight, 85% by weight, etc. These content amounts can also be expressed as "approximately". "Approximately" means plus or minus 10%, so for example, "approximately 1% by weight" means 0.9 to 1.1% by weight.

[0032] Examples of solid carriers include inorganic materials: minerals (natural silicates, marble, pumice, limestone, rare earth minerals, cryolite, activated clay, lime, activated carbon, talc, attapulgite, sodium montmorillonite, calcium montmorillonite, kaolinite, calcite, dolomite, diatomite, bentonite, zeolite, sepiolite, pyrophyllite, vermiculite, crystalline silica, amorphous silica, etc.), silicon dioxide, calcium sulfate, magnesium sulfate, barium sulfate, magnesium oxide, aluminum oxide, ammonium sulfate, ammonium phosphate, ammonium nitrate, calcium phosphate, sulfur, calcium carbonate, sodium bicarbonate, sodium carbonate, synthetic silicates, and their pulverized products; organic materials: grain powders (rice bran, rice flour, corn flour) Examples of solid carriers include: powders (such as wheat flour), sugars (cellulose, starch, lactose, glucose, fructose, sucrose, etc.), plant-derived powders (nut shell powders (such as coconut, walnut, and peanut shell powders), tree-derived powders (such as bark powder and sawdust), and other plant powders (such as tobacco stems, soybeans, and cottonseed husks)), lignin, wax, seashells, urea, polyethylene, polypropylene, polyvinyl alcohol, polycarbonate, polyester, polyamide, polyurethane, polyvinyl chloride, polyvinyl acetate, ethylene-vinyl acetate copolymer, ethylene-methyl methacrylate copolymer, polyvinylpyrrolidone-methacrylic acid copolymer, polyvinylpyrrolidone-vinyl acetate copolymer, cellulose derivatives, phenolic resins, melamine resins, and epoxy resins. Furthermore, the above solid carriers can also be used as adsorbent carriers.

[0033] Examples of liquid carriers include water, aliphatic hydrocarbons (hexane, 1-hexene, cyclohexane, octane, isooctane, 1-heptene, d-limonene, pinene, hexadecane, etc.), aromatic hydrocarbons (alkylbenzenes (toluene, xylene, isopropylbenzene, p-diethylbenzene, etc.), alkylbenzene derivatives, alkylnaphthalenes, alkylnaphthalene derivatives, tetrahydronaphthalene, etc.), chlorinated hydrocarbons (monochloroethylene, dichloroethylene, trichloroethylene, tetrachloroethylene, Dichloromethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane, 1,2-dichloropropane, etc.), ketones (cyclohexanone, acetone, 2-heptanone, isophorone, mesityl oxide, methylisoamyl ketone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone, diacetone alcohol, methylcyclohexanone, etc.), esters (fatty acid esters (ethyl acetate, butyl acetate, amyl acetate, isoamyl acetate, isobornyl acetate, hexyl acetate, heptyl acetate, octyl acetate, Isopropyl myristate, methyl octanoate, methyl oleate, methyl laurate, dibutyl adipate, tributyl citrate, and dibutyl phthalate, etc.), lactate esters (ethyl lactate, propyl lactate, etc.), carbonate esters (ethylene carbonate, propylene carbonate, butylene carbonate, diethyl carbonate, dibutyl carbonate, etc.), esterified polyols (glycerol acetate, glycol acetate, glycerin monoacetate, glycerin diacetate, glycerin triacetate, diethylene glycol abietate, di Propylene glycol dibenzoate, dipropylene glycol monomethyl ester, etc.), lactones (γ-butyrolactone, etc.), ethers (1,4-dioxane, tetrahydrofuran, dipropylene glycol methyl ether, ethylene glycol methyl ether, propylene glycol methyl ether, etc.), amides (N-octyl-caprolactam, N-dodecyl-caprolactam, N,N-dimethylformamide, fatty acid dimethylamides (N,N-dimethylacetamide, N,N-dimethyldecanamide, N,N-dimethyloctanamide, alkylpyrrolidones (N-methylpyrrolidone, N-octylpyrrolidone, N-dodecylpyrrolidone, etc.), lactams (α-lactam, β-lactam, γ-lactam, δ-lactam, etc.), amines (octylamine, octylamine acetate, oleylamine, diethanolamine, laurylamine, etc.), alcohols (methanol, ethanol, butanol, propanol, isopropanol, butanol, amyl alcohol, hexanol, heptanol, octanol, 2-ethylhexanol, etc.), hexylene glycol, cyclohexanol, phenol, benzyl alcohol, methoxypropanol (1-methoxy-2-propanol), tetrahydrofurfuryl alcohol, furfuryl alcohol, polyethylene glycol, ethylene glycol, diethylene glycol, hexylene glycol, ethylene glycol methyl ether, diethylene glycol Examples include methyl ether, diethylene glycol butyl ether, triethylene glycol, propylene glycol methyl ether, dipropylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol butyl ether, dipropylene glycol methyl ether, dipropylene glycol ether, dipropylene glycol monomethyl ether, glycerin, etc.), mineral oils (naphtha, petroleum ether, kerosene, diesel oil, paraffin, olefins, etc.), oils derived from animals and plants, oils derived from plants (palm oil, rapeseed oil, castor oil, coconut oil, soybean oil and their derivatives, etc.), oils derived from animals (sardine oil, saury oil, whale oil and their derivatives, etc.), dimethyl sulfoxide, silicone oil, acetonitrile, propanenitrile, acid anhydrides (acetic anhydride, etc.), triethyl phosphate, oleic acid, propionic acid, lactic acid, and xylene sulfonic acid.

[0034] These solid and liquid carriers may be used individually or in combination of two or more types.

[0035] Examples of gaseous carriers used in the present invention include fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide.

[0036] Examples of surfactants include anionic surfactants, cationic surfactants, amphoteric surfactants, and nonionic surfactants.

[0037] Examples of anionic surfactants include carboxylic acids, sulfonic acids, sulfate esters, and phosphate esters, specifically the following: Carboxylic acids: Fatty acid salts (octanoate, decanoate, laurate, myristicate, palmitate, stearate, behenate, oleate, polyoxyethylene alkyl ether carboxylates (laureth-3-carboxylate, α-(carboxymethyl)-ω-(dodecyloxy)poly(oxyethylene) salt, etc.), N-acyl sarcosine salts (N-lauroyl sarcosine salt, etc.), N-acyl glutamate salts (N-lauroyl glutamate, etc.), polycarboxylates (polyacrylates, polyvinyl acetates, comb-type polymers of polysaltes, and their derivatives, etc.) Sulfonic acids: Alkyl sulfonic acids and their salts (dodecyl sulfonate, etc.), alpha-olefin sulfonates (alkene (C14-18) hydroxysulfonate, alkapoliene (C12-20) hydroxysulfonate, alkene (C14-18) hydroxysulfonate, alkene (C12-20) hydroxysulfonate, tetradecene-1-sulfonate, α-olefin (C14-16) sulfonate, etc.), alkylbenzene sulfonates (decylbenzenesulfonate, dodecylbenzenesulfonate, tridecylbenzenesulfonate, diphenylsulfonate, etc.), alkylnaphthalene sulfonates (naphthalene sulfonate, 6-methyl-2-naphthalene sulfonate, dibutylnaphthalene sulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonates, diisopropylnaphthalene sulfonates, triisopropylnaphthalene sulfonates, 1-isopropyl-2-naphthalene sulfonates, etc.), sulfosuccinic acid, monoalkyl sulfosuccinates, dialkyl sulfosuccinates, (di(2-ethylhexyl) sulfosuccinate, etc.), N-methyl-N-acyl taurate salts (oleoylmethyl taurate, etc.), lignin sulfonates, alkylphenol sulfonates, naphthalene sulfonates-formaldehyde condensates, benzimidazole sulfonates and their derivatives, Sulfate esters: Alkyl sulfates (hexyl sulfate, heptyl sulfate, octyl sulfate, lauryl sulfate, lauryl sulfate diethanolate, hexadecyl sulfate, octadecyl sulfate, etc.), polyoxyethylene alkyl ether sulfates and their salts (laureth-3 sulfate, polyoxyethylene monotridecyl ether sulfate, α-sulfo-ω-hydroxyalkyl (C6-10) ether poly(oxyethylene) salt, etc.), polyoxyethylene alkylphenyl ether sulfates (poly(oxyethylene) 2-decylphenyl ether sulfate, poly(oxyethylene) 3-decylphenyl ether sulfate, α-sulfo-ω-[2,4-bis(1,1,3,3-tetramethylbutyl)phenoxy]poly(oxyethylene) salt, etc.), polyoxypropylene alkyl ether sulfates, lignosulfite wastewater, and derivatives thereof; Phosphate esters: Alkyl phosphates (propyl phosphate, hexadecyl phosphate, lauryl phosphate, dioctyl phosphate, etc.), polyoxyethylene alkyl ether phosphates (polyoxyethylene decyl phosphate, α-phosphono-ω-butoxypoly(oxyethylene), etc.), polyoxyethylene alkylphenyl ether phosphates (α-(dinonylphenyl)-ω-hydroxypoly(oxyethylene) phosphate, α-(dodecylphenyl)-ω-hydroxypoly(oxyethylene) phosphate, α-(nonylphenyl)-ω-hydroxypoly(oxyethylene) phosphate, etc.), polyoxypropylene alkyl ether phosphates, and their derivatives.

[0038] Cationic surfactants include, for example, amine salts and quaternary ammonium salts, specifically the following: Amine salts: alkylamine salts (monomethylamine salt, dimethylamine salt, trimethylamine salt, etc.), fatty acid amidoamine salts (stearamidopropyldimethylamine, behenamidopropyldimethylamine, etc.), polyamine salts (polyvinylamine, polyethyleneimine, etc.), and their derivatives; Quaternary ammonium salts: lauryltrimethylammonium salt, cetyltrimethylammonium salt, dodecyltrimethylammonium salt, stearyltrimethylammonium salt, benzalkonium chloride, benzethonium chloride, and benzylbis(2-chloroethyl) ethylammonium bromide salt.

[0039] Examples of amphoteric surfactants include betaine, alkylbetaine, alkyldimethylbetaine, imidazoline, taurine, alkyltaurine, dodecyldimethylammonium acetate, 4-carboxy-N,N,N-trimethyl-1-butanaminonium, 1-carboxy-N,N,N-2-2-tetramethyl-1-propanaminonium, N-alkyl (or alkenyl) (C12-18) glycine and its salts, N-dodecylglycine and its salts, and derivatives thereof.

[0040] Examples of nonionic surfactants include alcohols, amides, amines, esters, ethers, ether esters, and carboxylic acids, and specifically, the following are listed below. Alcohols: Aromatic alcohols (alkylphenols (allylphenol, octylphenol, nonylphenol, octyl cresol, etc.), acylphenols, etc.), aliphatic alcohols (isotridecyl alcohol, oleyl alcohol, cetyl alcohol, etc.), polyhydric alcohols (polysaccharides, starch, starch derivatives, sucrose, alkyl polyglucosides, sorbitan, ethoxylated sorbitan, cellulose derivatives, gum arabic, etc.), synthetic polymers (polyvinyl alcohol, polyethylene glycol, etc.); Amides: Alkanolamides (fatty acid alkanolamides (lauric acid diethanolamide, etc.), fatty acid glucamides (alkoxylated propylene oxide fatty acid glucamide, etc.), alkoxylated amides (polyoxyethylene oleamide, polyoxyethylene stearate amide, etc.), synthetic polymers (polyvinylpyrrolidone, etc.); Amines: Alkoxylated amines (polyoxyethylene oleylamine, α,α'-[(9-octadecenylimino)di2,1-ethandyl]bis(ω-hydroxy)polyoxyethylene, etc.); Esters: Fatty acid esters (fatty acid esters of polyols, monoglycerides, phospholipids, etc.), sugar-derived esters (sucrose fatty acid esters (sucrose stearate diester, etc.), sorbitan fatty acid esters (sorbitan oleic acid monoester, etc.), glucose esters, cellulose esters, etc.), synthetic polymers (vinyl acetate copolymers, polymethacrylic acid, copolymers of methacrylic acid and methacrylic acid esters, etc.);Ethers: Alcohol ethoxylates (aliphatic alcohol ethoxylates (tridecyl alcohol ethoxylate, isooctyl alcohol ethoxylate, lauryl alcohol ethoxylate, hexadecyl alcohol ethoxylate, stearyl alcohol ethoxylate, etc.)), alkylphenol ethoxylates (nonylphenol ethoxylate, tristyrylphenol ethoxylate, tributylphenol ethoxylate, octylphenol ethoxylate, etc.), arylalkylphenol ethoxylates, arylphenol ethoxylates (monobenzyl biphenol alcohol ethoxylate, etc.), alcohol propoxylates (aliphatic alcohol propoxylates, alkylphenol propoxylates, arylalkylphenol propoxylates, etc.), block polymers (polyethylene oxide and polypropylene oxide block polymers, polyethylene oxide block polymers, polypropylene oxide block polymers, alkanol and polyethylene oxide and polypropylene oxide block polymers, etc.); Ether esters: Polyoxyethylene fatty acid esters (polyoxyethylene castor oil ester, polyoxyethylene stearate ester, polyoxyethylene beef tallow fatty acid ester, etc.), polyoxyethylene sorbitan fatty acid esters (polyoxyethylene sorbitan monooleate ester, polyoxyethylene sorbitan trioleate ester, polyoxyethylene sorbitan monolaurate ester, polyoxyethylene sorbitan stearate ester, etc.), polyoxyethylene fatty acid amine esters, polyoxyethylene rosin esters, polyoxypropylene fatty acid esters (polyoxypropylene castor oil ester, etc.), polyoxypropylene fatty acid amine esters; Carboxylic acids: Undecafluorohexanoic acid.

[0041] These surfactants may be used individually or in combination of two or more types.

[0042] Examples of thickening agents include polysaccharides (xanthan gum, cellulose esters, cellulose ethers, carboxymethylcellulose and their salts, dextrin, starch, guar gum, gum arabic, hydroxypropyl guar gum, tyrose, carrageenan, etc.), clays (organic clay, organically modified clay, inorganic clay, inorganically modified clay, etc.), minerals (bentonite, attapulgite, silica, silicates, etc.), and synthetic polymers (polycarboxylates, polyacrylic acid derivatives, polyvinylpyrrolidone, polyvinyl alcohol, etc.). These thickening agents may be used individually or in combination of two or more.

[0043] Examples of protective colloidal agents include water-soluble celluloses such as methylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, and carboxymethylcellulose; polyalkylene glycols such as polyethylene glycol and polypropylene glycol; polyvinyl alcohol; polyvinylpyrrolidone; guar gum; gum arabic; gelatin; polyacrylates; and alginates. These protective colloidal agents may be used individually or in combination of two or more.

[0044] Examples of antifreeze agents include alcohols (ethylene glycol, propylene glycol, dipropylene glycol, triethylene glycol, ethylene glycol methyl ether, propylene glycol methyl ether, dipropylene glycol methyl ether, ethylene glycol butyl ether, glycerin, polyethylene glycol, etc.), esters (dipropylene glycol dibenzoate, glycerol acetate, glycerol diacetate, glycerol triacetate, gamma butyrolactone, etc.), ethers (1,4-dioxane, etc.), and urea. These antifreeze agents may be used individually or in combination of two or more.

[0045] Examples of defoaming agents include silicones (polysiloxane, diblock ethoxysiloxane, triblock ethoxysiloxane, etc.), alkyl sulfosuccinates, higher alcohols, higher alcohol derivatives, fatty acid salts, and fatty acid derivatives. These defoaming agents may be used individually or in combination of two or more.

[0046] Examples of antifungal agents include benzothiazole derivatives, sorbic acid, potassium sorbate, and butyl p-oxybenzoate. These antifungal agents may be used individually or in combination of two or more.

[0047] Examples of preservatives and disinfectants include phenols (orthophenylphenol, thymol, 3,5-dimethyl-4-chlorophenol, 2-isopropyl-5-methylphenol, 3-methyl-4-isopropylphenol), isothiazolinone derivatives (alkylisothiazolinones (5-chloro-2-methylisothiazolinone, 2-methylisothiazolinone, N-octylisothiazolinone), benzisothiazolinones (1,2-benzisothiazolinone, N-butylbenzoisothiazolinone), bronopol derivatives (bronopol benzyl alcohol hemifomal), parabens (methylparaben, ethylparaben, propylparaben, isopropylparaben, butylparaben, isobutylparaben, heptylparaben, benzylparaben), and imidazoles (thiabendazole). , 2-(4-thiazolyl)benzimidazole), 2-benzimidazolylcarbamate methyl, benzalkonium chloride, didecyldimethylammonium chloride, glyceryl caprylate, glyceryl caprate, glycerin fatty acid ester, sodium dehydroacetate, hinokitiol, silver zeolite, silver salt, methylene bisthiocyanate, 2-bromo-2-nitropropane-1,3-diol, glutaraldehyde, iodopropynyl butylcarbamate, 1,2-dibromo-2,4-dicyabutane, chlorhexidine gluconate, polyhexamethylene biguanide, parachlorometaxylenol, parachlorometacresol, polylysine, tetrachloroisophthalonitrile, diiodomethyl paratolylsulfone, parachlorophenyl-3-iodopropagylformal, 2,3,5,Examples include 6-tetrachloro-4-(methylsulfonyl)pyridine, lanthanum chloride, and rare earth salts (scandium salts, yttrium salts, lanthanum salts, cerium salts, praseodymium salts, neodymium salts, samarium salts, europium salts, gadolinium salts, terbium salts, dysprosium salts, holmium salts, erbium salts, thulium salts, ytterbium salts, and lutetium salts). Counterions include chloride salts, sulfate salts, nitrates, bromides, and iodides. Examples of preservatives and fungicides include carbonates, phosphates, organic acid salts, hydroxides, etc.), and organic acid salts include monovalent or divalent carboxylic acids and hydroxy acids. Specifically, examples of hydroxy acids include lactic acid, gluconic acid, tartaric acid, citric acid, malic acid, salicylic acid, etc., and examples of monovalent or divalent carboxylic acids include acetic acid, propionic acid, malonic acid, succinic acid, glutaric acid, adipic acid, azelaic acid, sorbic acid, benzoic acid, etc., as well as phosphoric acid and their salts. These preservatives and fungicides may be used alone or in combination of two or more.

[0048] Examples of antioxidants include phenols (2,6-di-t-butyl-p-cresol, 2,2'-methylenebis(4-methyl-6-t-butylphenol), etc.), amines (p,p'-dioctyldiphenylamine, N,N'-diphenyl-p-phenylenediamine, etc.), dibutylhydroxytoluene, butylhydroxyanisole, sodium erythorbate, sodium sulfite, potassium sulfite, potassium pyrosulfite, catechin, propyl gallate, sulfurs (didodecyl thiodipropionate, etc.), phosphoric acids (trisnonylphenyl phosphite, etc.), and vitamins (alpha-tocopherol, L-ascorbic acid, sodium ascorbate, ascorbyl palmitate, etc.). These antioxidants may be used individually or in combination of two or more.

[0049] Examples of light stabilizers include titanium dioxide, zinc oxide, activated carbon, carbon black, ethylhexyl methoxycinnamate, tert-butyl methoxydibenzoylmethane, hindered amines, ferulic acid, phenyl hydroxybenzoate, ethyl para-aminobenzoate, octyl salicylate, t-butylphenyl salicylate, 4-tert-octylphenyl salicylate, 2-cyano-3,3-diphenylpropane-2-enoic acid-2-ethylhexyl ester (octocrylene), drometrizole trisiloxane, 2,4,6-tris[4-(2-ethylhexyloxycarbonyl)anilino]-1,3,5-triazine (octyltriazone, TEAT), and 2,2'-methylenebis[6-(2H-benzotriazole-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol] (MBP). Examples include 2-ethylhexyl paradimethylaminobenzoate (EDB), homomenthyl salicylate (HS), phenylbenzimidazole sulfonic acid (PBS), hydroxymethoxybenzophenone sulfonic acid (oxybenzone 4, OXB4), sodium hydroxymethoxybenzophenone sulfonate (oxybenzone 5, OXB5), sodium dihydroxydimethoxybenzophenone disulfonate (oxybenzone 9, OXB9), tetrahydroxybenzophenone, dihydroxybenzophenone, dihydroxydimethoxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-ethylhexyl dimethoxybenzylidene dioxoimidazolidinepropionate, 2,4-dihydroxybenzophenone, and bis(2-methoxy-4-hydroxy-5-benzoylphenyl)methane. These light stabilizers may be used alone or in combination of two or more.

[0050] Examples of pH adjusting agents include sulfuric acid, nitric acid, hydrochloric acid, acetic acid, carbonic acid, oxalic acid, lactic acid, succinic acid, gluconic acid, citric acid, phosphoric acid, sorbic acid, and their salts, sodium bicarbonate, sodium hydroxide, potassium hydroxide, calcium hydroxide, aluminum hydroxide, copper hydroxide, and magnesium hydroxide. These pH adjusting agents may be used individually or in combination of two or more.

[0051] Examples of binders include polysaccharides (xanthan gum, cellulose esters, cellulose ethers, carboxymethylcellulose, hydroxypropyl guar gum, guar gum, natural gum arabic, synthetic gum arabic, dextrin, starch, carrageenan, etc.), clays (organic clay, organically modified clay, inorganic clay, inorganically modified clay), minerals (bentonite), synthetic polymers (polycarboxylic acids or their salts, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylic acid or its salts), and waxes (vegetable oils and fats, animal oils and fats, and their derivatives, paraffin, olefins, etc.). These binders may be used alone or in combination of two or more.

[0052] Examples of adhesives and spreading agents include the surfactants and liquid carriers described above (esters (alkyl fatty acid esters, sorbitan fatty acid esters, ethoxylated fatty acid esters, ethoxylated sorbitan fatty acids, etc.), alcohols (ethoxylated aliphatic alcohols, ethoxylated sorbitan aliphatic alcohols, etc.), waxes (vegetable oils, animal oils, and their derivatives, paraffin, olefins, etc.), vegetable oils (alkylated vegetable oils, etc.), mineral oils (mineral oil, etc.), silicone emulsions, synthetic polymers (styrene-butadiene copolymers, methyl methacrylate-butadiene copolymers, polyacrylic acid or its salts, polyvinyl acetate, polyvinyl alcohol, polyvinylpyrrolidone, polyethylene glycol, polypropylene glycol, etc.), and natural polymers (xanthan gum, cellulose esters, cellulose ethers, carboxymethylcellulose or its salts, dextrin, starch, guar gum, gum arabic, hydroxypropyl guar gum, tyrose, etc.). These adhesives and spreading agents may be used alone or in combination of two or more.

[0053] Examples of lubricants and lubricants include the alcohols, fatty acid esters, sucrose fatty acid esters, glycerin fatty acid esters, hydrocarbons, paraffin, ethylene wax, aliphatic amides, erucic acid amide, stearic acid amide, oleic acid amide, methylenebisstearate amide, ethylenebisstearate amide, metal soaps, lead stearate, zinc stearate, calcium stearate, magnesium stearate, mineral oil, vegetable oil, kerosene, diesel oil, etc. These lubricants and lubricants may be used individually or in combination of two or more.

[0054] Examples of anticaking agents include the solid and liquid carriers described above, calcium phosphate, sodium phosphate, sodium carbonate, sodium silicate, calcium silicate, magnesium silicate, potassium aluminum silicate, silicon dioxide, talc, sodium aluminosilicate, calcium aluminosilicate, bentonite, stearic acid, dimethylpolysiloxane, powdered cellulose, and the like. These anticaking agents may be used individually or in combination of two or more.

[0055] Examples of fragrances include hydrocarbons, α-limonene, β-caryophyllene, alcohols, cis-3-hexenol, linalool, farnesol, β-phenylethyl alcohol, aldehydes, 2,6-nonagenal, citral, α-hexyl cinnamic aldehyde, ketones, β-ionone, L-carbone, cyclopentadecanone, esters, linalyl acetate, benzyl benzoate, lactones, γ-undecalactone, phenols, eugenol, oxides, rose oxide, acetals, phenylacetaldehyde dimethyl acetal, α-pinene, β-pinene, etc. These fragrances may be used individually or in combination of two or more.

[0056] Examples of coating agents include natural rubber, synthetic rubber, resins (styrene-butadiene copolymer, polyacrylonitrile, polyester, polyamide, polyurethane, polyurea, polyether, rosin, melamine, etc.), waxes (vegetable oils, animal oils, and their derivatives, paraffin, olefins, etc.), polysaccharides (xanthan gum, cellulose ester, cellulose ether, carboxymethylcellulose or its salts, dextrin, starch, guar gum, gum arabic, hydroxypropyl guar gum, tyrose, starch xanthate, carrageenan, etc.), and proteins (gelatin, etc.). These coating agents may be used individually or in combination of two or more.

[0057] Examples of inclusion agents include cyclodextrins, α-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin. These inclusion agents may be used alone or in combination of two or more. <Bait>

[0058] In one embodiment of the present invention, the compound is applied as a bait containing an edible component to cockroach habitats or to locations where their appearance is expected. In this case, the insecticidal effect is mainly exerted by the compound being orally ingested by cockroaches.

[0059] When applying this compound as a bait, the application rate of the compound per square meter of the area intended to be protected from cockroaches should be 0.1 to 100 mg / m². 2 It can be applied in such a manner. The specific amount of this compound to be applied is 0.2 mg / m². 2 , 0.3 mg / m² 2 , 0.4 mg / m² 2 , 0.5 mg / m² 2 , 0.6 mg / m² 2 , 0.7 mg / m² 2 , 0.8 mg / m² 2 , 0.9 mg / m² 2 , 1 mg / m² 2 , 2 mg / m 2 , 3 mg / m² 2 , 4 mg / m² 2 , 5 mg / m² 2 , 6 mg / m² 2 7 mg / m²2 , 8 mg / m² 2 9 mg / m² 2 , 10 mg / m² 2 , 15 mg / m² 2 , 20 mg / m² 2 , 30 mg / m² 2 , 40 mg / m² 2 50 mg / m² 2 60 mg / m² 2 70 mg / m² 2 , 80 mg / m² 2 90 mg / m² 2 These are some examples.

[0060] When this compound is applied as a bait, the bait may contain, in addition to this compound, edible components, attractants, humectants, gelling agents, etc. The bait may further contain, if necessary, stabilizers, bittering agents, preservatives, excipients, solid or liquid carriers, etc. Examples of such bait forms include gel baits and solid baits.

[0061] When this compound is applied as a bait, the bait may contain 0.001 to 5% by weight of the compound. Specific examples of the compound content in the bait include, for example, 0.002% by weight, 0.003% by weight, 0.004% by weight, 0.005% by weight, 0.006% by weight, 0.007% by weight, 0.008% by weight, 0.009% by weight, 0.01% by weight, 0.02% by weight, 0.03% by weight, 0.04% by weight, 0.05% by weight, 0.06% by weight, 0.07% by weight, 0.08% by weight, 0.09% by weight, 0.1% by weight, 0.2% by weight, 0.3% by weight, 0.4% by weight, 0.5% by weight, 0.6% by weight, 0.7% by weight, 0.8% by weight, 0.9% by weight, 1% by weight, 2% by weight, 3% by weight, and 4% by weight.

[0062] Feeding components are generally ingredients added to bait products to attract pests. Examples of such feeding components include sugars, lipids, starches, proteins, amino acids, carbohydrates, vegetable flour, animal fats, vegetable oils, yeast extracts, and milk solids. Feeding components may also function as attractants, as described later.

[0063] Attractants are generally ingredients that have the effect of attracting pests, and may be colorants or flavorings. Examples of such attractants include fruits, plant extracts, fragrances, other animal or plant components, pheromones, or other ingredients known to attract target cockroaches.

[0064] A humectant is an ingredient that has the function of retaining moisture in the bait. Examples of such humectants include glycols and other polyols, glycerin, and sorbitol.

[0065] A gelling agent is a component that has the function of forming the matrix of a gel. Examples of such gelling agents include carrageenan, alginates, gellan gum, and xanthan gum.

[0066] When this compound is used as a gel bait, the gel bait may contain 0.001 to 5% by weight of this compound, 15 to 99% by weight of a food component and / or attractant, and 0.1 to 10% by weight of a gelling agent.

[0067] When this compound is used as a solid bait, the solid bait may contain 0.001 to 5% by weight of this compound, 40 to 99% by weight of a food component and / or attractant, and 0.05 to 10% by weight of a humectant.

[0068] When this compound is used as a gel bait, it can be applied by directly coating cockroach habitats or areas where their appearance is expected (e.g., floors, walls, furniture, etc.). Alternatively, the gel bait can be injected into a bait station and placed in cockroach habitats or areas where their appearance is expected (e.g., floors, under furniture, in furniture gaps, inside shelves, etc.).

[0069] When this compound is used as a solid bait, it can be applied by scattering it in places where cockroaches live or where their appearance is expected (e.g., floors, under furniture, in furniture crevices). Alternatively, the solid bait can be added to a bait station and placed in places where cockroaches live or where their appearance is expected (e.g., floors, under furniture, in furniture crevices, inside shelves, etc.).

[0070] <Residual spraying>

[0071] In one embodiment of the present invention, the compound is applied as a composition comprising at least one selected from the group consisting of a surfactant and an inert carrier to a place where cockroaches live or where their appearance is expected. In this case, the insecticidal effect is mainly exerted by cockroaches coming into contact with the compound remaining in the applied area.

[0072] When this compound is applied as a composition to a place where cockroaches live or where their appearance is expected, the composition may contain, in addition to this compound, a surfactant, an inert carrier, and other formulation aids. The surfactants, inert carriers, and other formulation aids used in the composition may be those described above.

[0073] In one embodiment of the present invention, when the compound is applied as a composition to a place where cockroaches live or where their appearance is expected, the composition preferably contains at least one selected from a surfactant, a solid carrier, a vegetable oil, and a fatty acid. The surfactant, solid carrier, vegetable oil, and fatty acid described above can be used.

[0074] When this compound is applied as a composition to a place where cockroaches live or where their appearance is expected, the composition may be a formulation such as an aqueous suspension, an oily suspension, an oil, an emulsion, a microemulsion, a microcapsule, a wettable powder, a granular wettable powder, a powder, a granule, a tablet, or an aerosol. If the composition is a formulation, these formulations may be applied as is to a place where cockroaches live or where their appearance is expected, or the formulation may be diluted with water or the like to prepare a spray solution which may be applied to a place where cockroaches live or where their appearance is expected. In this case, the composition is preferably an aqueous suspension, a microcapsule, a granular wettable powder, or a water-diluted solution of any of these.

[0075] In one embodiment of the present invention, the composition applied to a cockroach habitat or a place where its appearance is predicted is an aqueous suspension or a diluted aqueous solution thereof. Such an aqueous suspension may contain the present compound, a surfactant, a thickener, a preservative, and water.

[0076] In another embodiment of the present invention, the composition to be applied to a cockroach habitat or a place where its appearance is expected is a microencapsulated formulation or an aqueous dilution thereof. Such a microencapsulated formulation may contain the compound microencapsulated with a resin such as polyurethane, a surfactant, a thickener, a preservative, and water.

[0077] In another embodiment of the present invention, the composition applied to a cockroach habitat or a place where its appearance is expected is an aqueous dilution of a granular wettable powder. Such a granular wettable powder may contain the present compound, a surfactant, and a solid carrier.

[0078] Places where cockroaches live or are expected to appear include houses, commercial facilities, hospitals, train stations, airports, factories, offices, schools, accommodations, waste disposal facilities, livestock barns, warehouses, tents, vehicles, airplanes, ships, various products, the ground, forests, pastures, drainage ditches, etc. More specifically, places where cockroaches live or are expected to appear include walls, ceilings, floors, underfloors, pillars, transoms, windows, doors, or materials containing cellulose components (wood products), etc.

[0079] Treatment of cockroach habitats or areas where their appearance is predicted is carried out by spraying, coating, or vaporizing a composition containing the compound at the aforementioned locations.

[0080] Materials that can be used as habitats for cockroaches, or where their presence is predicted, include, but are not limited to, concrete (cement), brick, bamboo, wood, tile, ceramic, mud, metal, plastic, thatched roof, and corrugated iron.

[0081] When this compound is applied as a composition to a place where cockroaches live or where their appearance is expected, the content of this compound in the composition is preferably 0.0025 to 1.6% by weight, and more preferably 0.01 to 1% by weight. Specific concentrations of this compound include 0.003% by weight, 0.004% by weight, 0.005% by weight, 0.006% by weight, 0.007% by weight, 0.008% by weight, 0.009% by weight, 0.01% by weight, 0.02% by weight, 0.03% by weight, 0.04% by weight, 0.05% by weight, 0.06% by weight, 0.07% by weight, 0.08% by weight, 0.09% by weight, 0.1% by weight, 0.2% by weight, 0.3% by weight, 0.4% by weight, 0.5% by weight, 0.6% by weight, 0.7% by weight, 0.8% by weight, 0.9% by weight, 1% by weight, 1.1% by weight, 1.2% by weight, 1.3% by weight, 1.4% by weight, and 1.5% by weight.

[0082] The active ingredient of this compound can be immobilized on the surface of a cockroach habitat or a place where cockroaches are expected to appear by applying a composition containing this compound to the surface. The amount of this compound to be immobilized may be adjusted as appropriate depending on the timing of application, the location of application, the treatment method, etc. For example, the amount of this compound to be immobilized per unit area of ​​treatment area is 1 to 160 mg / m². 2 Examples include the amount of this compound per treatment area, for instance, 2 mg / m². 2 , 3 mg / m² 2 , 4 mg / m² 2 , 5 mg / m² 2 , 6 mg / m² 2 7 mg / m² 2 , 8 mg / m² 2 9 mg / m² 2, 10 mg / m² 2 , 15 mg / m² 2 , 20 mg / m² 2 , 25 mg / m² 2 , 30 mg / m² 2 , 35 mg / m² 2 , 40 mg / m² 2 50 mg / m² 2 60 mg / m² 2 70 mg / m² 2 , 80 mg / m² 2 90 mg / m² 2 , 100 mg / m² 2 , 110 mg / m² 2 , 120 mg / m² 2 , 130 mg / m² 2 , 140 mg / m² 2 , and 150 mg / m² 2 These are examples. The amount of this compound supported per unit area can also be expressed as "approximately." "Approximately" means plus or minus 10%, for example, "approximately 10 mg / m²." 2 "This refers to 9-11 mg / m² 2 That is the case.

[0083] In one embodiment of the present invention, applying the compound as a composition to a place where cockroaches live or where their appearance is expected maintains a cockroach control effect for one month. In other words, in this embodiment, sufficient and continuous cockroach control can be obtained by performing the above application once a month.

[0084] In another embodiment of the present invention, the compound is applied as a composition to a place where cockroaches live or where their appearance is expected, and the cockroach control effect is maintained for two, three, or four months.

[0085] In one embodiment of the present invention, applying the compound as a composition to a place where cockroaches live or where their appearance is expected maintains a cockroach control effect for one week. In other words, in this embodiment, sufficient and continuous cockroach control can be obtained by performing the above application once a week.

[0086] In another embodiment of the present invention, when the compound is applied as a composition to a place where cockroaches live or where their appearance is expected, the cockroach control effect is maintained for 2 weeks, 3 weeks, 4 weeks, 5 weeks, 6 weeks, 7 weeks, 8 weeks, 9 weeks, 10 weeks, 11 weeks, 12 weeks, 13 weeks, 14 weeks, 15 weeks, or 16 weeks.

[0087] The present invention will be described in more detail below with reference examples, manufacturing examples, formulation examples, and test examples, but the present invention is not limited to these examples.

[0088] First, we will show an example of how to prepare this compound.

[0089] When the physical properties of a compound are measured by liquid chromatography / mass spectrometry (hereinafter referred to as LCMS), the measured molecular ion value [M + H] + or [M-H] - The retention time (hereinafter referred to as RT) is also noted. The conditions for liquid chromatography (hereinafter referred to as LC) are as follows.

[0090] [LC Conditions] Column: L-column2 ODS, inner diameter 4.6 mm, length 35 mm, particle size 3 μm (Chemicals Evaluation and Research Institute) UV measurement wavelength: 254 nm Mobile phase: Solution A: 0.1% formic acid aqueous solution, Solution B: 0.1% formic acid acetonitrile Flow rate: 2.0 mL / min Pump: LC-20AD (Shimadzu Corporation) 2 units (high pressure gradient) Gradient conditions: Liquid is delivered with the concentration gradient described in Table 3.

[0091]

[0092] [MS Conditions] Detector: LCMS-2020 (Shimadzu Corporation) Ionization Method: DUIS

[0093] Reference Production Example 1 A mixture of 3.0 g of 3-bromo-1-(3-chloropyridine-2-yl)-1H-pyrazole-5-carboxylic acid (i.e., compound (R-1)) and 15 mL of THF was mixed with 2.1 mL of pyridine and 1.0 mL of methanesulfonyl chloride, and the mixture was stirred at 15°C for 30 minutes. Then, 2.5 g of 2-amino-3-bromo-5-chlorobenzoic acid, 2.1 mL of pyridine, and 1.0 mL of methanesulfonyl chloride were added in order, and the mixture was stirred at 15°C for 4 hours. Water was added to the resulting mixture, and the precipitate was washed with water and MTBE, and then dried under reduced pressure to obtain 4.3 g of intermediate 7 shown in the following formula.

[0094] Intermediate 7

[0095] The physical properties of the obtained intermediate 7 are shown below. Intermediate 7: 1 H-NMR (CDCl3) δ: 8.55 (1H, dd), 8.11 (1H, d), 7.97 (1H, dd), 7.91 (1H, d), 7.47 (1H, dd), 7.30 (1H, s).

[0096] Reference Manufacturing Example 2 Following Reference Manufacturing Example 1, formula (M-1): In X 1 , X 2 and X 3 An intermediate was produced in which the combination of the elements was one of the combinations listed in Table 4.

[0097]

[0098] The physical properties of the obtained intermediates are shown below. Intermediate 1: 1 H-NMR (CDCl3) δ: 8.52 (1H, dd), 7.95 (1H, dd), 7.65 (1H, m), 7.52-7.48 (1H, m), 7.27 (1H, s), 7.19 (1H, m). Intermediate 2: 1 H-NMR (CDCl3) δ: 8.52 (1H, d), 7.95 (2H, m), 7.50 (1H, dd), 7.42 (1H, d), 7.28 (1H, s). Intermediate 3: 1H-NMR (CDCl3) δ: 8.52 (1H, dd), 8.09 (1H, dd), 7.95 (1H, dd), 7.56 (1H, dd), 7.52-7.48 (1H, m), 7.28 (1H, s). Intermediate 5: 1 ¹H-NMR (CDCl₃) δ: 8.53 (¹H, dd), 7.95 (²H, m), 7.53–7.49 (¹H, m), 7.45–7.41 (¹H, m), 7.29 (¹H, s). Intermediate 6: 1 H-NMR (CDCl3) δ: 8.55 (1H, dd), 8.07 (1H, d), 7.97 (1H, dd), 7.73 (1H, d), 7.49 (1H, dd), 7.30 (1H, d). Intermediate 8: 1 ¹H-NMR (CDCl₃) δ: 8.49 (¹H, dd), 8.09 (²H, m), 7.92 (¹H, dd), 7.41 (¹H, dd), 7.25 (¹H, s). Intermediate 9: 1 H-NMR (CDCl3) δ: 8.53 (1H, dd), 8.10 (1H, dd), 7.96 (1H, dd), 7.57 (1H, dd), 7.53-7.49 (1H, m), 7.29 (1H, d). Intermediate 10: 1 H-NMR (CDCl3) δ: 8.55 (1H, dd), 8.22 (1H, d), 7.97 (1H, dd), 7.88 (1H, d), 7.49 (1H, dd), 7.31 (1H, s). Intermediate 11: 1 ¹H-NMR (CDCl₃) δ: 8.56 (¹H, d), 8.27 (¹H, s), 8.06 (¹H, d), 7.98 (¹H, d), 7.48 (¹H, dd), 7.31 (¹H, t). Intermediate 16: 1 ¹H-NMR (CDCl₃) δ: 8.54 (¹H, d), 8.47 (2H, m), 7.97 (¹H, d), 7.46 (¹H, dd), 7.30 (¹H, d). Intermediate 18: LCMS: 475 [M+H] +, RT = 2.06 min Intermediate 19: LCMS: 519[M+H] + , RT = 1.86 min Intermediate 22: 1 H-NMR (CDCl3) δ: 8.54 (1H, m), 7.97 (1H, m), 7.80 (1H, m), 7.48 (1H, m), 7.32 (1H, d). Intermediate 27: 1 H-NMR (CDCl3) δ: 8.54 (1H, dd), 8.12 (1H, d), 7.97 (1H, dd), 7.47 (1H, dd), 7.33 (1H, s). Intermediate 38: 1 H-NMR (CDCl3) δ: 8.54 (1H, dd), 7.95 (1H, t), 7.84 (1H, s), 7.47 (1H, dd), 7.32 (1H, s). Intermediate 43: LCMS: 597[M+H] + , RT = 2.25 minutes

[0099] Preparation Example 1 Following the method described in WO2023012081, 0.75 g of intermediate 7 and 30 mL of acetonitrile were mixed, to which 7.5 mL of ammonia-ethanol solution (2 mol / L) was added and the mixture was stirred at room temperature for 0.5 hours. Water was added to the resulting mixture and extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:cyclohexane = 30:70 to 95:5) to obtain 0.38 g of compound 7, represented by the following formula.

[0100] This compound 7

[0101] The physical properties of the obtained compound 7 are shown below. Compound 7: 1 H-NMR (CDCl3) δ: 8.47 (1H, d), 7.87 (1H, d), 7.71 (1H, d), 7.49 (1H, d), 7.39 (1H, dd), 7.04 (1H, s), 6.58 (1H, s), 5.61 (1H, s). LCMS: 534[M+H] + , RT = 1.66 minutes

[0102] Manufacturing Example 2 Following Manufacturing Example 1, formula (I): In X 1 , X 2 and X 3 The compound was prepared such that the combination of elements was one of the combinations listed in Table 5.

[0103]

[0104] The physical properties of the obtained compound are shown below. Compound 1: 1 H-NMR (CDCl3) δ: 9.72 (1H, s), 8.47 (1H, dd), 7.87 (1H, dd), 7.39 (1H, dd), 7.05 (3H, m), 6.08 (1H, s). LCMS: 458[M+H] + , RT = 1.51 min Present compound 2: 1 H-NMR (DMSO-D6) δ: 10.38 (1H, s), 8.44 (1H, dd), 8.08 (1H, dd), 7.70 (1H, s), 7.56 (2H, m), 7.50 (1H, s), 7.31-7.27 (2H, m). LCMS: 474[M+H] + , RT = 1.55 min Compound 3: 1 H-NMR (DMSO-D6) δ: 10.39 (1H, s), 8.46 (1H, dd), 8.09 (1H, dd), 7.72 (1H, dd), 7.66 (1H, s), 7.56 (1H, dd), 7.50 (1H, s), 7.33 (2H, m).LCMS: 518[M+H] + , RT = 1.56 min Compound 5: 9.96 (1H, s), 8.48 (1H, dd), 7.88 (1H, dd), 7.42-7.30 (3H, m), 7.01 (1H, d), 6.08 (1H, s), 5.69 (1H, s). LCMS: 474[M+H] + , RT = 1.61 min Compound 6: 1H-NMR (CDCl3) δ: 9.31 (1H, s), 8.47 (1H, dd), 7.87 (1H, dd), 7.54 (1H, d), 7.44 (1H, d), 7.39 (1H, dd), 7.03 (1H, s), 6.06 (1H, s), 5.63 (1H, s). LCMS: 490[M+H] + RT = 1.64 This compound 8: 1 H-NMR (CDCl3) δ:9.11 (1H, s), 8.48 (1H, dd), 7.93 (1H, d), 7.88 (1H, dd), 7.51 (1H, d), 7.40 (1H, dd), 7.09 (1H, s). LCMS: 582[M+H] + RT = 1.67. Compound 9: 9.99 (1H, s), 8.48 (1H, dd), 7.88 (1H, dd), 7.50 (1H, m), 7.42 (2H, m), 7.02 (1H, s), 6.07 (1H, s), 5.69 (1H, s). LCMS: 518 [M+H] + RT = 1.64 This compound 10: 1 H-NMR (CDCl3) δ:9.35 (1H, s), 8.48 (1H, dd), 7.88 (1H, dd), 7.70 (1H, d), 7.60 (1H, d), 7.40 (1H, dd), 7.04 (1H, s). LCMS: 534[M+H] + RT = 1.67 This compound 11: 1 H-NMR (CDCl3) δ: 8.47 (1H, s), 7.87 (2H, dd), 7.63 (1H, d), 7.39 (1H, dd), 7.05 (1H, s), 6.06 (1H, s), 5.60 (1H, s). LCMS: 480[M+H] + RT = 1.68 This compound 16: 1H-NMR (CDCl3) δ: 9.26 (1H, s), 8.46 (1H, dd), 8.25 (1H, d), 7.86 (1H, dd), 7.78 (1H, s), 7.41-7.37 (1H, m), 7.12 (1H, s), 6.11 (1H, s), 5.60 (1H, s). LCMS: 674[M+H] + RT = 1.74 This compound 18: 1 H-NMR (CDCl3) δ: 9.34 (1H, s), 8.48 (1H, d), 7.88 (1H, d), 7.41 (2H, m), 7.03 (1H, d), 6.23 (1H, s), 5.92 (1H, s). LCMS: 492[M+H] + RT = 1.59 This compound 19: 1 H-NMR (CDCl3) δ: 9.12 (1H, s), 8.49 (1H, d), 7.89 (1H, d), 7.57 (1H, s), 7.43 (1H, s), 7.04 (1H, s), 6.20 (1H, s), 5.88 (1H, s). LCMS: 536[M+H] + RT = 1.61 This compound 22: 1 H-NMR (CDCl3) δ: 9.58 (1H, s), 8.48 (1H, d), 7.88 (1H, d), 7.57 (1H, d), 7.40 (1H, dd), 7.07 (1H, m), 6.26 (1H, s), 5.94 (1H, s). LCMS: 508[M+H] + RT = 1.65 This compound 27: 1 H-NMR (CDCl3) δ: 9.38 (1H, s), 8.47 (1H, dd), 7.87 (2H, m), 7.39 (1H, dd), 7.08 (1H, d), 6.22 (1H, s), 5.90 (1H, s). LCMS: 598[M+H] + RT = 1.68 This compound 38: 1H-NMR (CDCl3) δ: 8.47 (1H, dd), 7.89 (1H, dd), 7.54 (1H, d), 7.41 (1H, dd), 7.18 (1H, s), 6.07 (1H, s), 5.87 (1H, s). LCMS: 524[M+H] + , RT = 1.70 min Compound 43: 1 H-NMR (THF-D8) δ: 9.91 (1H, s), 8.38 (1H, dd), 8.00 (1H, s), 7.93 (1H, dd), 7.41 (1H, dd), 7.08 (3H, t). LCMS: 614[M+H] + , RT = 1.71 minutes

[0105] The following are examples of formulations. Note that "parts" refers to parts by weight. In the examples of formulations, the abbreviation SX refers to any one compound selected from Compounds 1 to 48, their N oxides, their salts, or their solvates.

[0106] Formulation Example 1 A formulation is obtained by mixing 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and silica (weight ratio 1:1), 10 parts of SX, and 55 parts of water, and then finely grinding the mixture using a wet grinding method.

[0107] Formulation Example 2 A formulation is obtained by grinding and mixing 50 parts of SX, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of silica.

[0108] Formulation Example 3 A formulation is obtained by mixing 5 parts of SX, 9 parts of polyoxyethylene styrylphenyl ether, 5 parts of polyoxyethylene decyl ether (ethylene oxide addition number: 5), 6 parts of calcium dodecylbenzenesulfonate, and 75 parts of xylene.

[0109] Formulation Example 4: Two parts of SX, one part of silica, two parts of calcium ligninsulfonate, thirty parts of bentonite, and sixty-five parts of kaolin clay are crushed and mixed, an appropriate amount of water is added and kneaded, granulated in a granulator, and then dried to obtain the formulation.

[0110] Formulation Example 5: 10 parts of SX are mixed with a mixture of 18 parts of benzyl alcohol and 9 parts of DMSO. 6.3 parts of GERONOL® TE250, 2.7 parts of Ethylan NS-500LQ®, and 54 parts of solvent naphtha are added and mixed to obtain a formulation.

[0111] Formulation Example 6: A formulation is obtained by mixing 10 parts of SX, 5 parts of nonylphenol ethoxylate, and 85 parts of propylene glycol.

[0112] Formulation Example 7 A formulation is obtained by mixing 10 parts of SX and 20 parts of xylene and dispersing the mixture in 68 parts of water containing 2 parts of polyvinyl alcohol.

[0113] Formulation Example 8: 30 parts of SX, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate, and 65 parts of kaolin clay are crushed and mixed, an appropriate amount of water is added and kneaded, granulated in a granulator, and then dried to obtain the formulation.

[0114] Formulation Example 9: A mixture of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (weight ratio 1:1) is mixed with 10 parts of SX and 55 parts of water. The mixture is finely ground by a wet grinding method, and the resulting mixture is granulated using a fluidized bed granulator to obtain a formulation.

[0115] Formulation Example 10 A formulation is obtained by mixing 20 parts of SX, 5 parts of polyoxyethylene nonylphenyl ether, 3 parts of carboxymethylcellulose, and 72 parts of water.

[0116] Formulation Example 11: Mix 10 parts of SX, 0.2 parts of hexamethylene diisocyanate, and 10 parts of xylene, and disperse in 75.8 parts of water containing 2 parts of polyvinyl alcohol. Add 2 parts of ethylenediamine and proceed with the encapsulation reaction while mixing to obtain the formulation.

[0117] Formulation Example 12 A formulation is obtained by grinding and mixing 2 parts of SX, 88 parts of kaolin clay, and 10 parts of talc.

[0118] Formulation Example 13: Mix 60 parts of SX, 10 parts of special aromatic sodium sulfonate formalin condensate (product name: Demol SN-B, manufactured by Kao Corporation), 4 parts of sodium lauryl sulfate (product name: Emal 10 Powder, manufactured by Kao Corporation), and 26 parts of kaolin clay (product name: A Clay, manufactured by Katsumitsuyama Mining Co., Ltd.), then pulverize with an air mill. Next, add 11 parts of water to the pulverized material and knead well. The resulting mixture is granulated using a small extruder with a 0.7 mmφ screen, dried at 60°C for 10 minutes, and sized to obtain a granular wettable powder.

[0119] Formulation Example 14: Mix 50 parts of SX, 3.0 parts of sodium diisopropylnaphthalene sulfonate, 4.0 parts of sodium sulfomethylated lignin sulfonate, 0.25 parts of sodium cellulose carboxymethyl ether salt, 1.0 part of amorphous silica, and 41.75 parts of lactose, and grind with an air mill. Then, add 10 parts of water to the ground material and knead it. The resulting mixture is granulated using a small extruder with a 1.0 mmφ screen, dried at 60°C for 10 minutes, and granulated to obtain a granular wettable powder.

[0120] Formulation Example 15: Mix 43.4 parts of SX, 0.2 parts of a silicone-based antifoaming agent (product name: Xiameter ACP-1500 Antifoam compound, manufactured by Toray Dow Corning), 3.4 parts of polyoxyethylene tristyrylphenyl ether phosphate triethanolamine salt (product name: Soprofoll FL, manufactured by Syensqo), 4.3 parts of propylene glycol, and 20.5 parts of deionized water, and wet grind the mixture in a bead mill to obtain a suspension. Next, 0.3 parts of aluminum magnesium silicate (trade name: BeeGum®, manufactured by Vanderbilt Minerals, LLC), 0.2 parts of xanthan gum (trade name: Kelzan, manufactured by CP Kelco), and 0.2 parts of a preservative (containing 1,2-benzoisothiazolin-3-one as the active ingredient, trade name: Proxel GXL, manufactured by Lonza) are mixed, dissolved, and dispersed in 27.5 parts by weight of deionized water to prepare a thickening agent solution, which is then mixed with the above-mentioned suspension to obtain an aqueous suspension pesticide composition.

[0121] Formulation Example 16: A formulation is obtained by mixing and dissolving 0.1 parts of SX and 39.9 parts of kerosene, placing the mixture in an aerosol container, and filling it with 60 parts of liquefied petroleum gas (a mixture of propane, butane, and isobutane; saturated vapor pressure: 0.47 MPa (25°C)).

[0122] Formulation Example 17: 40 parts of SX, 0.4 parts of a silicone-based antifoaming agent (product name: Xiameter ACP-1500 Antifoam compound, manufactured by Toray Dow Corning), 8 parts of a mixture of 40% by mass of polyoxyethylene tristyrylphenyl ether potassium phosphate and 60% by mass of propylene glycol (product name: Soprofor FLK, manufactured by Syensqo), and 51.6 parts of deionized water are mixed and wet-milled using a bead mill to obtain a suspension.

[0123] Formulation Example 18: Mix and dissolve 0.1 parts of SX, 8.9 parts of a paraffinic solvent (Neothiosol, manufactured by Chuo Kasei Co., Ltd.), and 1 part of sorbitan monooleate (Leodol SP-O10, manufactured by Kao Corporation). Place this mixture and 50 parts of water into an aerosol container and fill with 40 parts of liquefied petroleum gas (a mixture of propane, butane, and isobutane; saturated vapor pressure: 0.47 MPa (25°C)) to obtain the formulation.

[0124] Formulation Example 19: Mix 2 parts of SX, 2 parts of pregelatinized starch (Amicol H, manufactured by Nippon Denki Chemical Co., Ltd.), 0.5 parts of zinc oxide (manufactured by Seido Chemical Industry Co., Ltd.), and 75.4 parts of azodicarbonamide (Uniform AZ, manufactured by Otsuka Chemical Co., Ltd.), granulate, and dry to obtain a cylindrical formulation (diameter in the circular direction approximately 3 mm, length approximately 7 mm).

[0125] Formulation Example 20: Mix 0.5 parts of SX, 25 parts of starch syrup, 1 part of gellan gum, and 34.5 parts of water to obtain a formulation.

[0126] Formulation Example 21: Add 1 part of SX to a pressure-resistant glass container, fill the pressure-resistant glass container with 99 parts of liquefied carbon dioxide at 20°C, and stir-mix to obtain a formulation containing 1% by weight of SX.

[0127] Formulation Example 22: Mix 40 parts of SX, 0.4 parts of a silicone-based antifoaming agent (product name: Xiameter ACP-1500 Antifoam compound, manufactured by Toray Dow Corning), 6.4 parts of Atlox4913 (polymethyl methacrylate-polyethylene glycol graft copolymer, manufactured by CRODA), 1.6 parts of Atlox4894 (polyoxyethylene alkyl ether, manufactured by CRODA), and 51.6 parts of deionized water, and obtain a suspension by wet grinding using a bead mill.

[0128] Formulation Example 23 A formulation is obtained by mixing 5 parts of SX, 15 parts of tridecyl alcohol ethoxylate (trade name: MAKON TD-3, manufactured by Stepan), 60 parts of dimethyl sulfoxide, and 20 parts of propylene glycol.

[0129] Next, the pest control effect of the present invention will be demonstrated in a test example.

[0130] The excellent control effect of this compound against cockroaches can be confirmed, for example, from the following test examples.

[0131] <1. Residual Spray Test> Test Example 1-1 (2.5 mg / m²) 2 (After leaving the tile to stand for 1 day) A suspension of compound 6 was prepared according to Formulation Example 17. A diluted aqueous solution of the suspension of compound 6 was applied to a tile (15 cm x 15 cm) at a rate of 2.5 mg / m² of compound 6. 2The tile was sprayed in the following manner. As a negative control, water was sprayed on another tile. The sprayed tile was left undisturbed indoors for one day. Ten adult German cockroaches (5 males and 5 females) were placed in a plastic cup (diameter: 10 cm) coated with Fluon® PTFE AD911E on the wall surface. The treated tile was placed over the cup so that the treated surface was on the inside, and it was fixed in place. The cup was then inverted and the test insects were in contact with the tile for one hour. After one hour, the cup was inverted and the tile was removed. The test insects were given food and water, and the number of individuals suffering from distress and those that died was investigated after 7 days. The distress death rate (%) was calculated using formula 1 below. The distress death rate in the treated group was corrected using Abbott's correction shown in formula 2 below, using the distress death rate of the negative control. Note that a dead individual refers to an individual that has completely stopped moving, and a distressed individual refers to an individual that cannot get up when placed on its back. [Equation 1] Bitterness death rate (%) = {(Number of dead individuals + Number of individuals suffering) / Number of individuals tested} × 100 [Equation 2] Corrected bitterness death rate = (Bitterness death rate in the treated group - Bitterness death rate in the negative control) / (100 - Bitterness death rate in the negative control) × 100 The same tests were conducted for compounds 7, 8, 10, 11, and 16. As a result of the tests, compounds 6, 7, 8, 10, 11, and 16 all showed a corrected bitterness death rate of 60% or more.

[0132] Test Example 1-2 (10 mg / m²) 2 (Tile standing for 1 day) Use compound 3 instead of compound 6, and the amount of compound 3 to be treated is 10 mg / m² 2 Except as otherwise provided, the bitter insect mortality rate and corrected bitter insect mortality rate were determined according to the method described in Test Example 1-1. Compounds 5, 6, 7, 8, 10, 11, 16, 22, 27, and 38 were tested in the same manner. As a result of the tests, compounds 3, 5, 6, 7, 8, 10, 11, 16, 22, 27, and 38 all showed a corrected bitter insect mortality rate of 70% or higher.

[0133] Test Example 1-3 (40 mg / m²) 2 (Tile standing for 1 day) Use compound 2 instead of compound 6, and the amount of compound 2 to be treated is 40 mg / m² 2Except as otherwise provided, the bitter insect mortality rate and corrected bitter insect mortality rate were determined according to the method described in Test Example 1-1. Compounds 3, 5, 6, 7, 8, 9, 10, 11, 16, 18, 19, 22, 27, and 38 were tested in the same manner. As a result of the tests, compounds 2, 3, 5, 6, 7, 8, 9, 10, 11, 16, 18, 19, 22, 27, and 38 all showed a corrected bitter insect mortality rate of 70% or higher.

[0134] Test Example 1-4 (2.5 mg / m²) 2 Except for allowing the tiles to stand for four weeks after application (after treatment with compound 6), the bitter insect mortality rate and corrected bitter insect mortality rate for compound 6 were determined according to the method described in Test Example 1-1. Compounds 7, 8, 10, 11, and 16 were tested in the same manner. As a result of the tests, compounds 6, 7, 8, 10, 11, and 16 all showed a corrected bitter insect mortality rate of 60% or more.

[0135] Test Example 1-5 (10 mg / m²) 2 (Tile standing for 4 weeks) Use compound 2 instead of compound 6, and the amount of compound 2 to be treated is 10 mg / m² 2 Except for setting the tiles for 4 weeks after application (after treatment with compound 2), the bitter insect mortality rate and corrected bitter insect mortality rate were determined according to the method described in Test Example 1-1. Compounds 3, 5, 6, 7, 8, 10, 11, 16, 22, and 27 were tested in the same manner. As a result of the tests, compounds 2, 3, 5, 6, 7, 8, 10, 11, 16, 22, and 27 all showed a corrected bitter insect mortality rate of 60% or higher.

[0136] Test Example 1-6 (40 mg / m²) 2 (Tile standing for 4 weeks) Use compound 2 instead of compound 6, and the amount of compound 2 to be treated is 40 mg / m² 2 Except for setting the tiles for 4 weeks after application (after treatment with compound 2), the bitter insect mortality rate and corrected bitter insect mortality rate were determined according to the method described in Test Example 1-1. Compounds 3, 5, 6, 7, 8, 9, 10, 11, 16, 18, 19, 22, 27, and 38 were tested in the same manner. As a result of the tests, compounds 2, 3, 5, 6, 7, 8, 9, 10, 11, 16, 18, 19, 22, 27, and 38 all showed a corrected bitter insect mortality rate of 60% or higher.

[0137] Test Example 1-7 (2.5 mg / m²) 2 Except for allowing the tiles to stand for 12 weeks after application (after treatment with compound 6), the bitter insect mortality rate and corrected bitter insect mortality rate for compound 6 were determined according to the method described in Test Example 1-1. Compounds 7, 8, 10, 11, and 16 were tested in the same manner. As a result of the tests, compounds 6, 7, 8, 10, 11, and 16 all showed a corrected bitter insect mortality rate of 60% or more.

[0138] Test Example 1-8 (10 mg / m²) 2 (Tile standing for 12 weeks) Use compound 3 instead of compound 6, and the amount of compound 3 to be treated is 10 mg / m² 2 Except for setting the tiles for 12 weeks after application (after treatment with compound 3), the bitter insect mortality rate and corrected bitter insect mortality rate were determined according to the method described in Test Example 1-1. Compounds 6, 7, 8, 10, 11, 16, 22, 27, and 38 were tested in the same manner. As a result of the tests, compounds 3, 6, 7, 8, 10, 11, 16, 22, 27, and 38 all showed a corrected bitter insect mortality rate of 60% or higher.

[0139] Test Example 1-9 (40 mg / m²) 2 (Tile standing for 12 weeks) Use compound 2 instead of compound 6, and the amount of compound 2 to be treated is 40 mg / m² 2 Except for setting the tiles for 12 weeks after application (after treatment with compound 2), the bitter insect mortality rate and corrected bitter insect mortality rate were determined according to the method described in Test Example 1-1. Compounds 3, 5, 6, 7, 8, 9, 10, 11, 16, 18, 19, 22, 27, and 38 were tested in the same manner. As a result of the tests, compounds 2, 3, 5, 6, 7, 8, 9, 10, 11, 16, 18, 19, 22, 27, and 38 all showed a corrected bitter insect mortality rate of 60% or higher.

[0140] <2. Direct Oil Spray Test> Test Example 2-1 Margarine was applied to the wall surface to prevent escape, and 10 adult German cockroaches (5 males and 5 females) were released into a plastic cup (diameter: 10 cm, height: 4.5 cm) lined with filter paper. The cup was then placed in the center of the bottom of a box-shaped chamber (46 cm x 46 cm x height 70 cm). 1.5 mL of a 0.004 wt% formulation of Compound 3 (a formulation obtained by dissolving Compound 3 in a mixture of isopropyl alcohol, dimethyl sulfoxide, and Isopar M (an isoparaffinic solvent manufactured by ExxonMobil) in a weight ratio of 35:15:50, and adjusting the concentration of Compound 3 to 0.004 wt%) was sprayed into the cup from a height of 60 cm above the bottom of the cup using a spray gun (RG-3L ANEST IWATA AIR) at a spray pressure of 0.041 MPa. After spraying, the test insects were transferred to a new cup, given food and water, and the number of dead and suffering individuals was investigated 7 days after the spraying. The percentage of insects that died from suffering was calculated using the following formula 1. A dead individual is defined as an individual that has completely ceased activity, and a suffering individual is defined as an individual that cannot get up when placed on its back. [Formula 1] Percentage of insects that died from suffering (%) = {(Number of dead individuals + Number of suffering individuals) / Number of test individuals} × 100 The same test was conducted for compounds 6, 7, 10, 22, and 27. The test results showed that compounds 3, 6, 7, 10, 22, and 27 all exhibited a percentage of insects that died from suffering of 60% or more.

[0141] Test Example 2-2 The insect mortality rate was determined according to the method described in Test Example 2-1, except that a 0.02% by weight formulation of Compound 2 (a formulation obtained by dissolving Compound 2 in a mixture of isopropyl alcohol, dimethyl sulfoxide, and Isopar M in a weight ratio of 35:15:50, and adjusting the concentration of Compound 2 to 0.02% by weight) was used instead of a 0.004% by weight formulation of Compound 3. The same tests were conducted for Compounds 3, 5, 6, 7, 8, 9, 10, 16, 18, 19, 22, 27, and 38. The test results showed that Compounds 2, 3, 5, 6, 7, 8, 9, 10, 16, 18, 19, 22, 27, and 38 all showed an insect mortality rate of 60% or more.

[0142] Test Example 2-3: The insect mortality rate was determined according to the method described in Test Example 2-1, except that a 0.1% by weight formulation of Compound 1 (prepared by dissolving Compound 1 in a mixture of isopropyl alcohol, dimethyl sulfoxide, and Isopar M in a weight ratio of 35:15:50, and adjusting the concentration of Compound 1 to 0.1% by weight) was used instead of a 0.004% by weight formulation of Compound 3. The same tests were conducted for Compounds 2, 3, 5, 6, 7, 8, 9, 10, 16, 18, 19, 22, 27, and 38. The test results showed that all of Compounds 1, 2, 3, 5, 6, 7, 8, 9, 10, 16, 18, 19, 22, 27, and 38 exhibited an insect mortality rate of 60% or higher.

[0143] Test Example 2-4: Instead of a 0.004 wt% formulation of Compound 3, a 0.02 wt% formulation of Compound 8 was used (a formulation obtained by dissolving Compound 8 in a mixture of isopropyl alcohol, dimethyl sulfoxide, and Isopar M in a weight ratio of 35:15:50, and adjusting the concentration of Compound 8 to 0.02 wt%). Instead of 10 adult German cockroaches (5 males and 5 females), 4 adult American cockroaches (2 males and 2 females) were used, and instead of a plastic cup (diameter: 10 cm, height: 4.5 cm), a plastic cup (diameter: 10 cm, height: 8 cm) was used. The insect mortality rate was determined according to the method described in Test Example 2-1. Compound 16 was tested in the same manner. The test results showed that both Compound 8 and 16 exhibited an insect mortality rate of 60% or more.

[0144] In Test Example 2-5, the insect mortality rate was determined according to the method described in Test Example 2-1, except that a 0.02% by weight formulation of Compound 27 was used instead of a 0.004% by weight formulation of Compound 3 (a formulation obtained by dissolving Compound 27 in a mixture of isopropyl alcohol, dimethyl sulfoxide, and isopar M in a weight ratio of 35:15:50, and adjusting the concentration of Compound 27 to 0.02% by weight), 6 adult American cockroaches (3 males and 3 females) were used instead of 10 adult German cockroaches (5 males and 5 females), and a plastic cup (diameter: 10 cm, height: 8 cm) was used instead of a plastic cup (diameter: 10 cm, height: 4.5 cm), and the insect mortality rate was determined according to the method described in Test Example 2-1. The test results showed that Compound 27 exhibited an insect mortality rate of 60% or more.

[0145] Test Example 2-6: Instead of a 0.004 wt% formulation of Compound 3, a 0.1 wt% formulation of Compound 2 was used (a formulation obtained by dissolving Compound 2 in a mixture of isopropyl alcohol, dimethyl sulfoxide, and Isopar M in a weight ratio of 35:15:50, and adjusting the concentration of Compound 2 to 0.1 wt%). Instead of 10 adult German cockroaches (5 males and 5 females), 4 adult American cockroaches (2 males and 2 females) were used, and instead of a plastic cup (diameter: 10 cm, height: 4.5 cm), a plastic cup (diameter: 10 cm, height: 8 cm) was used. The rate of insect death from the bitterness was determined according to the method described in Test Example 2-1. Compounds 3, 7, 8, 10, 16, and 38 were tested in the same manner. As a result of the tests, Compounds 2, 3, 7, 8, 10, 16, and 38 all showed a rate of insect death from the bitterness of 60% or more.

[0146] Test Example 2-7: Instead of a 0.004 wt% formulation of Compound 3, a 0.1 wt% formulation of Compound 6 was used (a formulation obtained by dissolving Compound 6 in a mixture of isopropyl alcohol, dimethyl sulfoxide, and Isopar M in a weight ratio of 35:15:50, and adjusting the concentration of Compound 6 to 0.1 wt%). Instead of 10 adult German cockroaches (5 males and 5 females), 6 adult American cockroaches (3 males and 3 females) were used, and instead of a plastic cup (diameter: 10 cm, height: 4.5 cm), a plastic cup (diameter: 10 cm, height: 8 cm) was used. The rate of insect death from bitterness was determined according to the method described in Test Example 2-1. Compounds 22 and 27 were tested in the same manner. The results showed that Compounds 6, 22, and 27 all exhibited a rate of insect death from bitterness of 60% or more.

[0147] Test Example 2-8: Instead of a 0.004 wt% formulation of Compound 3, a 0.02 wt% formulation of Compound 7 was used (a formulation obtained by dissolving Compound 7 in a mixture of isopropyl alcohol, dimethyl sulfoxide, and isopar M in a weight ratio of 35:15:50, and adjusting the concentration of Compound 7 to 0.02 wt%). Instead of 10 adult German cockroaches (5 males and 5 females), 4 adult American cockroaches (2 males and 2 females) were used, and instead of a plastic cup (diameter: 10 cm, height: 4.5 cm), a plastic cup (diameter: 10 cm, height: 8 cm) was used. The insect mortality rate was determined according to the method described in Test Example 2-1. Compounds 8 and 16 were tested in the same manner. The test results showed that Compounds 7, 8, and 16 all exhibited an insect mortality rate of 60% or more.

[0148] In Test Example 2-9, the insect mortality rate was determined according to the method described in Test Example 2-1, except that a 0.02% by weight formulation of Compound 27 was used instead of a 0.004% by weight formulation of Compound 3 (a formulation obtained by dissolving Compound 27 in a mixture of isopropyl alcohol, dimethyl sulfoxide, and isopar M in a weight ratio of 35:15:50, and adjusting the concentration of Compound 27 to 0.02% by weight), 6 adult Oriental cockroaches (3 males and 3 females) were used instead of 10 adult German cockroaches (5 males and 5 females), and a plastic cup (10 cm in diameter, 8 cm in height) was used instead of a plastic cup (10 cm in diameter, 4.5 cm in height). The test results showed that Compound 27 exhibited an insect mortality rate of 60% or more.

[0149] In Test Example 2-10, the insect mortality rate was determined according to the method described in Test Example 2-1, except that a 0.1% by weight formulation of Compound 2 was used instead of a 0.004% by weight formulation of Compound 3 (a formulation obtained by dissolving Compound 2 in a mixture of isopropyl alcohol, dimethyl sulfoxide, and isopar M in a weight ratio of 35:15:50, and adjusting the concentration of Compound 2 to 0.1% by weight), 4 adult Oriental cockroaches (2 males and 2 females) were used instead of 10 adult German cockroaches (5 males and 5 females), and a plastic cup (diameter: 10 cm, height: 8 cm) was used instead of a plastic cup (diameter: 10 cm, height: 4.5 cm), and the insect mortality rate was determined according to the method described in Test Example 2-1. Compounds 3, 7, 8, 10, 16, and 19 were tested in the same manner. As a result of the tests, Compounds 2, 3, 7, 8, 10, 16, and 19 all showed an insect mortality rate of 60% or more.

[0150] In Test Example 2-11, the insect mortality rate was determined according to the method described in Test Example 2-1, except that a 0.1% by weight formulation of Compound 6 was used instead of a 0.004% by weight formulation of Compound 3 (a formulation obtained by dissolving Compound 6 in a mixture of isopropyl alcohol, dimethyl sulfoxide, and isopar M in a weight ratio of 35:15:50, and adjusting the concentration of Compound 6 to 0.1% by weight), 6 adult Oriental cockroaches (3 males and 3 females) were used instead of 10 adult German cockroaches (5 males and 5 females), and a plastic cup (10 cm in diameter, 8 cm in height) was used instead of a plastic cup (10 cm in diameter, 4.5 cm in height). The same procedure was followed for Compounds 22 and 27. As a result of the tests, Compounds 6, 22, and 27 all showed an insect mortality rate of 60% or more.

[0151] <3. Food Toxicity Test> Test Example 3-1 Compound 3 was dissolved in acetone to prepare an acetone solution of Compound 3. A predetermined amount of this solution was dropped onto rat powder feed (CLEA Rodent Diet CE-2), and the resulting composition was air-dried to obtain a test feed. The concentration of Compound 3 in the test feed was 5 ppm. The test feed was placed in a plastic cup (diameter: 10 cm, height: 4.5 cm) along with 10 adult German cockroaches (5 males and 5 females) and cotton wool soaked in water. Fourteen days after placing the test feed, cockroaches, and cotton wool in the cup, the number of dead and suffering individuals was investigated, and the rate of death due to suffering (%) was calculated using the following formula 1. A dead individual refers to an individual that has completely stopped moving, and a suffering individual refers to an individual that cannot get up when placed on its back. [Formula 1] Bitterness death rate (%) = {(Number of dead individuals + Number of individuals suffering) / Number of individuals tested} × 100 The same test was conducted for compounds 6, 7, 8, 10, 11, 16, 22, and 27. The test results showed that compounds 3, 6, 7, 8, 10, 11, 16, 22, and 27 all exhibited a bitterness death rate of 60% or more.

[0152] In Test Example 3-2, the rate of insect deaths due to bitterness was determined according to the method described in Test Example 3-1, except that compound 2 was used instead of compound 3, and the concentration of compound 2 in the test feed was set to 50 ppm. The same tests were conducted for compounds 3, 5, 6, 7, 8, 9, 10, 11, 16, 18, 19, 22, 27, and 38. As a result of the tests, compounds 2, 3, 5, 6, 7, 8, 9, 10, 11, 16, 18, 19, 22, 27, and 38 all showed a rate of insect deaths due to bitterness of 60% or more.

[0153] In Test Example 3-3, the rate of insect deaths due to bitterness was determined according to the method described in Test Example 3-1, except that Compound 1 was used instead of Compound 3, and the concentration of Compound 1 in the test feed was set to 500 ppm. The same tests were conducted for Compounds 2, 3, 5, 6, 7, 8, 9, 10, 11, 16, 18, 19, 22, 27, and 38. As a result of the tests, Compounds 1, 2, 3, 5, 6, 7, 8, 9, 10, 11, 16, 18, 19, 22, 27, and 38 all showed a rate of insect deaths due to bitterness of 60% or more.

[0154] In Test Example 3-4, the concentration of compound 3 in the test feed was set to 50 ppm. Four adult American cockroaches (two males and two females) were used instead of ten adult German cockroaches (five males and five females), and a plastic cup (diameter: 10 cm, height: 10 cm) was used instead of a plastic cup (diameter: 10 cm, height: 4.5 cm). The rate of insect death due to bitterness was determined according to the method described in Test Example 3-1. The test results showed that compound 3 exhibited a bitterness-induced insect death rate of 60% or more.

[0155] Test Example 3-5: Compound 2 was used instead of Compound 3, the concentration of Compound 2 in the test feed was set to 500 ppm, 4 adult American cockroaches (2 males and 2 females) were used instead of 10 adult German cockroaches (5 males and 5 females), and plastic cups (10 cm in diameter and 10 cm in height) were used instead of plastic cups (10 cm in diameter and 4.5 cm in height). The rate of insect death due to bitterness was determined according to the method described in Test Example 3-1. Compounds 3, 7, 8, 16, 18, and 19 were tested in the same manner. The test results showed that all of the compounds 2, 3, 7, 8, 16, 18, and 19 exhibited a rate of insect death due to bitterness of 60% or more.

[0156] Test Example 3-6: Compound 6 was used instead of Compound 3, the concentration of Compound 6 in the test feed was set to 500 ppm, 6 adult American cockroaches (3 males and 3 females) were used instead of 10 adult German cockroaches (5 males and 5 females), and plastic cups (10 cm in diameter and 10 cm in height) were used instead of plastic cups (10 cm in diameter and 4.5 cm in height). The rate of insect death due to bitterness was determined according to the method described in Test Example 3-1. Compounds 11, 22, and 27 were tested in the same manner. The test results showed that Compounds 6, 11, 22, and 27 all exhibited a rate of insect death due to bitterness of 60% or more.

[0157] Test Example 3-7: Compound 1 was used instead of Compound 3, the concentration of Compound 1 in the test feed was set to 5000 ppm, 4 adult American cockroaches (2 males and 2 females) were used instead of 10 adult German cockroaches (5 males and 5 females), and plastic cups (10 cm in diameter and 10 cm in height) were used instead of plastic cups (10 cm in diameter and 4.5 cm in height). The bitterness mortality rate was determined according to the method described in Test Example 3-1. Compounds 2, 3, 7, 8, 9, 16, 18, 19, and 38 were tested in the same manner. The test results showed that all of the bitterness mortality rates for Compounds 1, 2, 3, 7, 8, 9, 16, 18, 19, and 38 were 60% or higher.

[0158] Test Example 3-8: Compound 6 was used instead of Compound 3, the concentration of Compound 6 in the test feed was set to 5000 ppm, 6 adult American cockroaches (3 males and 3 females) were used instead of 10 adult German cockroaches (5 males and 5 females), and plastic cups (10 cm in diameter and 10 cm in height) were used instead of plastic cups (10 cm in diameter and 4.5 cm in height). The rate of insect death due to bitterness was determined according to the method described in Test Example 3-1. Compounds 11, 22, and 27 were tested in the same manner. The test results showed that Compounds 6, 11, 22, and 27 all exhibited a rate of insect death due to bitterness of 60% or more.

[0159] Test Example 3-9: The method for determining the insect mortality rate was followed, except that Compound 8 was used instead of Compound 3, the concentration of Compound 8 in the test feed was set to 50 ppm, 4 adult Oriental cockroaches (2 males and 2 females) were used instead of 10 adult German cockroaches (5 males and 5 females), and a plastic cup (10 cm in diameter and 10 cm in height) was used instead of a plastic cup (10 cm in diameter and 4.5 cm in height). The results showed that Compound 8 had an insect mortality rate of 60% or more.

[0160] In Test Example 3-10, the rate of insect death due to bitterness was determined according to the method described in Test Example 3-1, except that Compound 11 was used instead of Compound 3, the concentration of Compound 11 in the test feed was set to 50 ppm, 6 adult Oriental cockroaches (3 males and 3 females) were used instead of 10 adult German cockroaches (5 males and 5 females), and plastic cups (10 cm in diameter and 10 cm in height) were used instead of plastic cups (10 cm in diameter and 4.5 cm in height). The same test was conducted for Compound 27. As a result of the test, both Compound 11 and 27 showed a rate of insect death due to bitterness of 60% or more.

[0161] Test Example 3-11 The concentration of compound 3 in the test feed was set to 500 ppm, and 4 adult American cockroaches (2 males and 2 females) were used instead of 10 adult German cockroaches (5 males and 5 females). Plastic cups (10 cm in diameter and 10 cm in height) were used instead of plastic cups (10 cm in diameter and 4.5 cm in height). Except for these differences, the rate of insect death due to bitterness was determined according to the method described in Test Example 3-1. Compounds 7, 8, 10, 16, 18, 19, and 38 were tested in the same manner. As a result of the tests, compounds 3, 7, 8, 10, 16, 18, 19, and 38 all showed a rate of insect death due to bitterness of 60% or more.

[0162] In Test Example 3-12, the rate of insect death due to bitterness was determined according to the method described in Test Example 3-1, except that compound 6 was used instead of compound 3, the concentration of compound 6 in the test feed was set to 500 ppm, 6 adult American cockroaches (3 males and 3 females) were used instead of 10 adult German cockroaches (5 males and 5 females), and plastic cups (10 cm in diameter and 10 cm in height) were used instead of plastic cups (10 cm in diameter and 4.5 cm in height). The same tests were conducted for compounds 11, 22, and 27. As a result of the tests, compounds 6, 11, 22, and 27 all showed a rate of insect death due to bitterness of 60% or more.

[0163] In Test Example 3-13, the rate of insect death due to bitterness was determined according to the method described in Test Example 3-1, except that Compound 1 was used instead of Compound 3, the concentration of Compound 1 in the test feed was set to 5000 ppm, 4 adult Oriental cockroaches (2 males and 2 females) were used instead of 10 adult German cockroaches (5 males and 5 females), and plastic cups (10 cm in diameter and 10 cm in height) were used instead of plastic cups (10 cm in diameter and 4.5 cm in height). The same tests were conducted for Compounds 2, 3, 5, 7, 8, 9, 10, 16, 18, 19, and 38. As a result of the tests, Compounds 1, 2, 3, 5, 7, 8, 9, 10, 16, 18, 19, and 38 all showed a rate of insect death due to bitterness of 60% or more.

[0164] In Test Example 3-14, the rate of insect death due to bitterness was determined according to the method described in Test Example 3-1, except that compound 6 was used instead of compound 3, the concentration of compound 6 in the test feed was set to 5000 ppm, 6 adult American cockroaches (3 males and 3 females) were used instead of 10 adult German cockroaches (5 males and 5 females), and plastic cups (10 cm in diameter and 10 cm in height) were used instead of plastic cups (10 cm in diameter and 4.5 cm in height). The same tests were conducted for compounds 11, 22, and 27. As a result of the tests, compounds 6, 11, 22, and 27 all showed a rate of insect death due to bitterness of 60% or more.

[0165] The present invention provides an amide compound exhibiting excellent efficacy and a method for controlling cockroaches.

Claims

1. Equation (I): (In formula (I), X 1 X represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. 2 X represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. 3 A method for controlling cockroaches, comprising the step of applying a compound represented by (where represents a hydrogen atom, a fluorine atom, or a chlorine atom), its N oxide, salts thereof, or solvates thereof, to cockroaches, their habitat, or places where their appearance is expected.

2. The method of controlling cockroaches according to claim 1, wherein the cockroach belongs to the order Blattodea, excluding the suborder Termites.

3. The method of controlling cockroaches according to claim 1, wherein the cockroaches belong to the genus Blattella or Periplaneta.

4. The method of controlling cockroaches according to claim 1, wherein the cockroach is the German cockroach (Blattella germanica).

5. The method of controlling cockroaches according to claim 1, wherein the cockroach is the American cockroach (Periplaneta americana).

6. The application rate of the compound represented by formula (I), its N oxide, their salts, or their solvates is 0.1 to 160 mg / m². 2 The pest control method according to any one of claims 1 to 5.

7. A method for controlling cockroaches according to any one of claims 1 to 6, wherein a composition comprising a compound represented by formula (I), its N oxide, a salt thereof, or a solvate thereof, selected from the group consisting of surfactants and inert carriers, is applied to cockroaches, their habitat, or a place where their appearance is predicted.

8. A method for controlling cockroaches according to any one of claims 1 to 6, wherein a compound represented by formula (I), its N oxide, a salt thereof, or a solvate thereof is applied as a bait containing a food component to a place where cockroaches live or where their appearance is predicted.

9. The method of controlling cockroaches according to claim 8, wherein the compound represented by formula (I), its N oxide, a salt thereof, or a solvate thereof is applied as a bait containing a food component to the habitat of cockroaches or to the place where their appearance is expected, thereby causing the compound represented by formula (I), its N oxide, a salt thereof, or a solvate thereof to be orally ingested by cockroaches.

10. A method for controlling cockroaches according to any one of claims 1 to 6, wherein a composition comprising a compound represented by formula (I), its N oxide, a salt thereof, or a solvate thereof, selected from the group consisting of surfactants and inert carriers, is applied to a place where cockroaches live or where their appearance is predicted.

11. A method for controlling cockroaches according to claim 10, comprising applying a composition containing at least one selected from the group consisting of a surfactant and an inert carrier to a place where cockroaches live or where their appearance is expected, thereby bringing the compound represented by formula (I), its N oxide, its salt, or its solvate remaining at the applied location into contact with the cockroaches.

12. The method for controlling cockroaches according to claim 10 or 11, wherein the control effect on cockroaches is maintained for three months by applying a compound represented by formula (I), its N oxide, their salts, or their solvates.

13. Formula (II): (In Formula (II), X 1a represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and when X 1a is a fluorine atom, X 2a and X 3a is a combination where X 2a is an iodine atom and X 3a is a fluorine atom, a combination where X 2a is a chlorine atom and X 3a is a hydrogen atom, or a combination where X 2a is an iodine atom and X 3a is a chlorine atom; when X 1a is a chlorine atom, X 2a represents an iodine atom and X 3a represents a fluorine atom; when X 1a is a bromine atom, X 2a represents an iodine atom and X 3a represents a hydrogen atom, a fluorine atom, or a chlorine atom; when X 1a is an iodine atom, X 2a represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and X 3a represents a hydrogen atom, a fluorine atom, or a chlorine atom.), an N-oxide thereof, a salt thereof or a solvate thereof.

14. A composition comprising the compound described in claim 13, its N oxide, salts thereof, or solvates thereof, and an inert carrier.

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