PYRIDINIUM SALT AND PEST CONTROL AGENT

Abstract

Provided are: a compound represented by Formula (I) or Formula (II) (wherein A represents an oxygen atom or a sulfur atom, X.sup.1 represents a substituted or unsubstituted C1-6 alkyl group or the like, m is any integer of 0 to 5, X.sup.2 represents a C2-8 haloalkyl group or the like, X.sup.3 represents a halogeno group or the like, n is any integer of 0-4, Z.sup.q− is a counter ion, and q is 1 or 2); and a pest control agent containing the compound as an active agent.

##STR00001##

Claims

1. A compound of formula (I) or formula (II): ##STR00044## in the formulae (I) and (II), A is an oxygen atom or a sulfur atom, X.sup.1 is a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C2-6 alkenyloxy group, a substituted or unsubstituted C2-6 alkynyloxy group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5- or 6-membered heteroaryl group, a substituted or unsubstituted 5- or 6-membered heteroaryloxy group, a substituted or unsubstituted C6-10 arylcarbonyl group, a substituted or unsubstituted 5- or 6-membered heteroarylcarbonyl group, a group of R.sup.aR.sup.bN—, a group of R.sup.aR.sup.bN—CO—, a group of R.sup.cCO—NH—, a pentafluorosulfanyl group, a nitro group, or a cyano group, m indicates a number of X.sup.1 and is an integer of 0 to 5, R.sup.a is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R.sup.b is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R.sup.c is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, X.sup.2 is a C5-8 alkyl group, a C2-8 haloalkyl group, a (substituted or unsubstituted C6-10 aryl) C1-6 alkyl group, a (substituted or unsubstituted 5- or 6-membered heteroaryl) C1-6 alkyl group, a (substituted or unsubstituted C6-10 aryloxy) C1-6 alkyl group, a (substituted or unsubstituted 5- or 6-membered heteroaryloxy) C1-6 alkyl group, a C3-6 alkenyl group, a C2-6 haloalkenyl group, a (substituted or unsubstituted C6-10 aryl) C2-6 alkenyl group, a (substituted or unsubstituted 5- or 6-membered heteroaryl) C2-6 alkenyl group, a C2-6 alkynyl group, a C2-6 haloalkynyl group, a (substituted or unsubstituted C6-10 aryl) C2-6 alkynyl group, a (substituted or unsubstituted 5- or 6-membered heteroaryl) C2-6 alkynyl group, a hydroxy group, a substituted C1-8 alkoxy group, a substituted or unsubstituted C2-6 alkenyloxy group, a substituted or unsubstituted C2-6 alkynyloxy group, a C2-6 alkylcarbonyl group, a substituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5- or 6-membered heteroaryloxy group, a substituted or unsubstituted C6-arylcarbonyl group, a substituted or unsubstituted 5- or 6-membered heteroarylcarbonyl group, a carbamoyl group, a group of R.sup.a1R.sup.b1N—, a group of R.sup.a1R.sup.b1N—CO—, a group of R.sup.a1R.sup.b1N—CO—N(R.sup.d1)—, a group of R.sup.a1R.sup.b1N—CS—N(R.sup.d1)—, a group of R.sup.c1CO—N(R.sup.d1)—, a group of R.sup.e1O—N═CR.sup.f1—, a group of R.sup.g1SO.sub.2—N(R.sup.d1)—, a group of R.sup.g1SO.sub.2NH—N═CR.sup.f1—, or a pentafluorosulfanyl group, R.sup.a1 is a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R.sup.b1 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R.sup.a1 and R.sup.b1 may be bonded together to form a divalent organic group, R.sup.c1 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group, R.sup.d1 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R.sup.e1 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R.sup.f1 is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, R.sup.g1 is a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, X.sup.3 is a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxy group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a pentafluorosulfanyl group, a nitro group, or a cyano group, n indicates a number of X.sup.3 and is an integer of 0 to 4, Z.sup.q− is a counter ion, and q is a valence of the counter ion and is 1 or 2).

2. A pest control agent comprising at least one selected from compounds of claim 1 as an active ingredient thereof.

3. An insecticide or acaricide comprising at least one selected from compounds of claim 1 as an active ingredient thereof.

4. An ectoparasite control agent comprising at least one selected from compounds of claim 1 as an active ingredient thereof.

5. An endoparasite control agent or expellant comprising at least one selected from compounds of claim 1 as an active ingredient thereof.

Description

EXAMPLES

(Preparation Formulation)

[0256] Although some preparation formulations of the pest control agent, insecticide, acaricide, ectoparasite control agent, endoparasite control agent or expellant according to the present invention are shown below, additives and addition amounts thereof are not limited to these examples, and may be varied in a wide range. In the preparation formulation, the term “part” indicates “parts by mass” and the term “%” indicates “% by mass”.

[0257] The agricultural, horticultural or paddy preparation formulations are shown below.

Formulation Example 1: Wettable Powders

[0258] 40 parts of a compound according to the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfuric acid ester, and 3 parts of alkyl naphthalene sulfonate are mixed uniformly, and then finely pulverized to obtain wettable powders containing 40% of the active ingredient.

Formulation Example 2: Emulsion

[0259] 30 parts of a compound according to the present invention, 33 parts of xylene, 30 parts of dimethylformamide, and 7 parts of polyoxyethylene alkyl allyl ether are mixed and dissolved to obtain an emulsion containing 30% of the active ingredient.

Formulation Example 3: Granules

[0260] 5 parts of a compound according to the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are mixed uniformly, and then finely pulverized, followed by conducting granulation to obtain a particle diameter of 0.5 to 1.0 mm, and thus granules containing 5% of the active ingredient are obtained.

Formulation Example 4: Granules

[0261] 5 parts of a compound according to the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of sodium dioctyl sulfosuccinate, and 1 part of potassium phosphate are mixed well and then pulverized, followed by adding water thereto, and then kneading the mixture. Then, granulation and drying are conducted to obtain granules containing 5% of the active ingredient.

Formulation Example 5: Suspension

[0262] 10 parts of a compound according to the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of sodium polycarboxylate, 10 parts of glycerin, 0.2 parts of xanthan gum, and 73.8 parts of water are mixed, and then wet-pulverized until the particle size becomes 3 m or less to obtain a suspension containing 10% of the active ingredient.

[0263] Preparation formulations of ectoparasite control agents, endoparasite control agents or expellants are shown below.

Formulation Example 6: Granules

[0264] 5 parts of a compound according to the present invention is dissolved in an organic solvent to obtain a solution. The solution is sprayed on a mixture of 94 parts of kaolin and 1 part of white carbon, followed by evaporating the solvent under reduced pressure to obtain granules. The granules may be mixed with animal feed to be used.

Formulation Example 7: Injection Agent

[0265] 0.1 to 1 part of a compound according to the present invention and 99 to 99.9 parts of peanut oil are mixed uniformly, and then filter-sterilized using a sterilizing filter.

Formulation Example 8: Pour-on Agent

[0266] 5 parts of a compound according to the present invention, 10 parts of a myristic acid ester and 85 parts of isopropanol are mixed uniformly to obtain a pour-on agent.

Formulation Example 9: Spot-on Agent

[0267] 10 to 15 parts of a compound according to the present invention, 10 parts of a palmitic acid ester and 75 to 80 parts of isopropanol are mixed uniformly to obtain a spot-on agent.

Formulation Example 10: Spray Agent

[0268] 1 part of a compound according to the present invention, 10 parts of propylene glycol and 89 parts of isopropanol are mixed uniformly to obtain a spray agent.

[0269] The present invention is explained further specifically by showing synthesis examples below. The present invention is not limited to the following examples.

Example 1

Synthesis of pyridin-1-ium-1-yl(4-((4-(trifluoromethyl)phenyl)ethynyl)benzoyl) amide

[0270] ##STR00010##

[0271] 4-((4-(Trifluoromethyl)phenyl)ethynyl)benzoic acid (0.06 g) was dissolved in thionyl chloride (2 ml), and one drop of pyridine was added thereto, followed by stirring the mixture at room temperature for 3 hours. The resultant liquid was concentrated under reduced pressure. Chloroform (8 ml), 1-aminopyridinium iodide (0.05 g) and triethylamine (0.06 g) were added to the resultant concentrate, and then the mixture was stirred at room temperature for 1 hour. Water was added to the resultant, and the mixture was subjected to extraction with chloroform. An organic layer was dried with anhydrous magnesium sulfate and filtered, and then the solvent was distilled off. The resultant residue was washed by adding diethyl ether thereto, and thus 0.06 g of the titled compound was obtained at a yield of 75%.

Example 2

Synthesis of (E)-Pyridin-1-ium-1-yl(4-(4-(trifluoromethyl)styryl)benzoyl)amide

[0272] ##STR00011##

[0273] (E)-4-(4-(trifluoromethyl)styryl)benzoic acid (0.43 g) was dissolved in toluene (20 ml), and then thionyl chloride (0.54 g) and one drop of pyridine were added thereto, followed by stirring the mixture while heating the mixture to reflux for 1 hour. The resultant was concentrated under reduced pressure. Chloroform (20 ml), 1-aminopyridinium iodide (0.33 g) and triethylamine (0.45 g) were added to the resultant concentrate, and then stirred at room temperature for 30 minutes. Water was added to the resultant, and the mixture was subjected to extraction with chloroform. An organic layer was dried with anhydrous magnesium sulfate and filtered, and then the solvent was distilled off. The resultant residue was washed by adding diethyl ether and acetone thereto, and thus 0.25 g of the titled compound was obtained at a yield of 45%.

Example 3

Synthesis of (4-(2-(4-chlorophenyl)cyclopropyl)benzoyl)(pyridin-1-ium-1-yl) amide

[0274] ##STR00012##

[0275] (4-(2-(4-Chlorophenyl)cyclopropyl)benzoic acid (0.17 g) was dissolved in dichloromethane (5 ml), and then oxalyl chloride (0.24 g) and one drop of DMF were added thereto, followed by stirring the mixture at room temperature for two hours. The resultant was concentrated under reduced pressure. Dichloromethane (8 ml), 1-aminopyridinium iodide (0.13 g) and triethylamine (0.38 g) were added to the resultant concentrate, followed by stirring the mixture at room temperature for one hour. Water was added to the resultant, and then the mixture was subjected to extraction with chloroform. An organic layer was dried with anhydrous magnesium sulfate and filtered, and then the solvent was distilled off. A mixture solvent composed of dichloromethane and methanol was added to the resultant residue to allow recrystallization to proceed, and thus 0.17 g of the titled compound was obtained at a yield of 90%.

Example 4

Synthesis of 1-(4-(4-(trifluoromethoxy)benzoyl)benzamide)pyridinium intramolecular salt

[0276] ##STR00013##

[0277] Thionyl chloride (5 ml) and pyridine (three drops) were added to 4-(4-(trifluoromethoxy)benzoyl)benzoic acid (0.87 g), and then refluxed for one hour. The resultant liquid was left to cool. Then, the solvent was distilled off. Chloroform (20 ml), N-aminopyridinium iodide (0.62 g) and triethylamine (0.85 ml) were added to the resultant residue, and then the mixture was stirred at room temperature for 17 hours. The resultant was put in an appropriate amount of water, and then subjected to extraction with chloroform. An organic layer was dried with anhydrous magnesium sulfate, and then the solvent was distilled off. The resultant solid was washed with diethyl ether to obtain the desired compound (0.6 g).

[0278] The 4-(4-(trifluoromethoxy)benzoyl)benzoic acid was prepared by the method described in WO2002092552.

Example 5

Synthesis of 1-(4-(3,3,3-trifluoro-1-propin-1-yl)benzamide)pyridinium intramolecular salt

[0279] ##STR00014##

[0280] Thionyl chloride (5 ml) and pyridine (three drops) were added to 4-(3,3,3-trifluoro-1-propin-1-yl)benzoic acid (0.55 g), and then the mixture was refluxed for one hour. The resultant liquid was left to cool. Then, the solvent was distilled off. Chloroform (18 ml), N-aminopyridinium iodide (0.49 g) and triethylamine (0.79 ml) were added to the resultant residue, and the mixture was stirred at room temperature for 17 hours. The resultant was put in an appropriate amount of water, and then subjected to extraction with chloroform. An organic layer was dried with anhydrous magnesium sulfate, and then the solvent was distilled off, followed by washing the resultant solid with diethyl ether to obtain the desired compound (0.5 g).

[0281] The 4-(3,3,3-trifluoro-1-propin-1-yl)benzoic acid was prepared by the method described in WO2006093832.

Example 6

Synthesis of 1-(4-((1E)-3,3,3-trifluoro-1-propen-1-yl)benzamide)pyridinium intramolecular salt

[0282] ##STR00015##

[0283] Thionyl chloride (2 ml) and pyridine (one drop) were added to 4-((1E)-3,3,3-trifluoro-1-propen-1-yl)benzoic acid (0.21 g), and then the mixture was refluxed for one hour. The resultant liquid was left to cool. The solvent was distilled off, and then chloroform (10 ml), N-aminopyridinium iodide (0.28 g) and triethylamine (0.41 ml) were added to the residue, and then the mixture was stirred at room temperature for 17 hours. The resultant was put in an appropriate amount of water, and then subjected to extraction with chloroform. An organic layer was dried with anhydrous magnesium sulfate, and then the solvent was distilled off. The resultant solid was washed with diethyl ether to obtain the desired compound (0.19 g).

[0284] The 4-((1E)-3,3,3-trifluoro-1-propen-1-yl)benzoic acid was prepared by the method described in Synthesis 1981, 5, 365.

Example 7

Synthesis of 1-(4-(2,2,3,3,4,4,5,5,5-nonafluoropentoxy)benzamide)pyridinium intramolecular salt

[0285] ##STR00016##

[0286] 2,2,3,3,4,4,5,5,5-Nonafluoropentanol (0.28 g), tris(dibenzylideneacetone) dipalladium (33 mg), 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (20 mg), cesium carbonate (0.24 g), and toluene (3 ml) were added to 1-(4-bromobenzamide)pyridinium intramolecular salt (0.1 g), and then reacted at 150° C. for 60 minutes using a microwave synthesizer. Toluene was distilled off from the resultant, and then the resultant was purified by silica gel column chromatography to obtain the desired compound (0.15 g).

[0287] The 1-(4-bromobenzamide)pyridinium intramolecular salt was prepared by the method described in GB1419377.

Example 8

Synthesis of 1-(4-((2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl)thio)benzamide) pyridinium intramolecular salt

[0288] ##STR00017##

[0289] 2,2,3,3,4,4,5,5,6,6,6-Undecafluorohexyl trifulate (0.75 g), potassium carbonate (0.36 g), and DMF (6 ml) were added to 4-mercaptobenzoic acid (0.26 g), and then reacted at room temperature for two hours. Water was added to the resultant, and the mixture was subjected to extraction by ethyl acetate. An organic layer was washed with saturated saline, dried with anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The resultant concentrate was purified by silica gel column chromatography to obtain 4-((2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl)thio)benzoic acid (0.4 g). Thionyl chloride (1 ml) and toluene (1 ml) were added to the resultant, and then the mixture was refluxed for one hour. The resultant liquid was left to cool. Then, the solvent was distilled off. Dichloromethane (2 ml), N-aminopyridinium iodide (0.11 g) and triethylamine (0.14 ml) were added to the resultant residue, and the mixture was stirred at room temperature for 17 hours. The resultant was put in an appropriate amount of hydrochloric acid, and then subjected to extraction with ethyl acetate. An organic layer was dried with anhydrous magnesium sulfate, and then the solvent was distilled off, followed by washing the resultant solid with diethyl ether to obtain the desired compound (0.15 g).

[0290] The 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl triflate was prepared by the method described in EP 646575.

Example 9

Synthesis of 1-(4-((2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl)sulfinyl)benzamide) pyridinium intramolecular salt

[0291] ##STR00018##

[0292] Dichloromethane (1 ml) was added to 1-(4-((2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl)thio)benzamide)pyridinium intramolecular salt (0.12 g), and then cooled to 0° C. Meta-chloroperbenzoic acid (0.09 g) was added to the resultant, and then reacted at room temperature for five hours. An aqueous sodium bicarbonate solution was added to the resultant liquid, and then the mixture was subjected to extraction by dichloromethane. An organic layer was washed with sodium sulfite, dried with anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The resultant solid was washed with diethyl ether to obtain the desired compound (0.12 g).

Example 10

Synthesis of 1-(4-(1,1,2-trifluoro-2-(perfluoropropoxy)ethoxy)benzamide) pyridinium intramolecular salt

[0293] ##STR00019##

[0294] DMF (10 ml), potassium tert-butoxide (0.075 g), and perfluoro(propyl vinyl ether) (0.62 ml) were added to methyl 4-hydroxybenzoate (0.5 g), and reacted at room temperature for 18 hours. Water was added to the resultant liquid, and then the mixture was subjected to extraction by ethyl acetate. An organic layer was washed with saturated saline, dried with an anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The resultant concentrate was purified by silica gel column chromatography to obtain methyl 4-(1,1,2-trifluoro-2-(perfluoropropoxy)ethoxy)benzoate (1.2 g). THF (2 ml), ethanol (2 ml), water (8 ml), and lithium hydroxide monohydrate (0.46 g) were added thereto, and then reacted at 50° C. for 60 minutes. Hydrochloric acid was added to the resultant, and the mixture was subjected to extraction by ethyl acetate. An organic layer was washed with saturated saline, dried with anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure to obtain 4-(1,1,2-trifluoro-2-(perfluoropropoxy)ethoxy)benzoic acid (1.0 g). Thionyl chloride (1 ml), toluene (1 ml) and DMF (one drop) were added thereto, and then the mixture was refluxed for one hour. The resultant liquid was left to cool. The solvent was distilled off, and then dichloromethane (10 ml), N-aminopyridinium iodide (0.26 g) and triethylamine (0.3 ml) were added to the residue, and the mixture was stirred at room temperature for 17 hours. The resultant was put in an appropriate amount of hydrochloric acid, and then subjected to extraction with ethyl acetate. An organic layer was dried with anhydrous magnesium sulfate, and then the solvent was distilled off. The resultant residue was purified by silica gel column chromatography to obtain the desired compound (0.4 g).

Example 11

Synthesis of pyridin-1-ium-1-yl(4-((4-(trifluoromethoxy)phenyl)carbamoyl) benzoyl)amide

(Step 1)

Synthesis of (4-formylbenzoyl)(pyridin-1-ium-1-yl)amide

[0295] ##STR00020##

[0296] 4-Formylbenzoic acid (0.90 g) was dissolved in dichloromethane (20 mL), and then 1-aminopyridinium iodide (1.1 g), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.1 g), 1-hydroxybenzotriazole hydrate (0.92 g) and triethylamine (1.2 g) were added thereto, followed by stirring the mixture at room temperature for 20 hours. Water was added to the resultant, and then the mixture was subjected to extraction by dichloromethane. The solvent was distilled off under reduced pressure to obtain the desired compound (0.84 g).

Melting point: 223° C. to 225° C.

(Step 2)

Synthesis of (4-carboxybenzoyl)(pyridin-1-ium-1-yl)amide

[0297] ##STR00021##

[0298] A t-butanol (10 mL) and water (3 mL) were added to (4-formylbenzoyl)(pyridin-1-ium-1-yl)amide (0.57 g). NaH.sub.2PO.sub.4 (2.4 g) and isobutene (1.4 g) were added to the mixture. NaClO.sub.2 (0.36 g) was added thereto, and stirred for five hours. The precipitate was filtered to obtain the desired compound (0.42 g).

Melting point: 230° C. to 232° C.

(Step 3)

Synthesis of pyridin-1-ium-1-yl(4-((4-(trifluoromethoxy)phenyl)carbamoyl) benzoyl)amide

[0299] ##STR00022##

[0300] (4-Carboxybenzoyl)(pyridin-1-ium-1-yl)amide (0.10 g) was dissolved in dichloromethane (4 mL), and then 4-(trifluoromethoxy)aniline (0.09 g), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.10 g), 1-hydroxybenzotriazole hydrate (0.08 g), and triethylamine (0.05 g) were added thereto, followed by stirring the mixture at room temperature for 41 hours. The precipitate was washed with water to obtain the desired compound (0.05 g).

Example 12

Synthesis of (E)-pyridin-1-ium-1-yl(4-(((2,2,2-trifluoroethoxy)imino)methyl) benzoyl)amide

[0301] ##STR00023##

[0302] (4-Formylbenzoyl)(pyridin-1-ium-1-yl)amide (45 mg) was dissolved in pyridine (1 mL). O-(2,2,2-trifluoroethyl)hydroxylamine (45 mg) was added thereto, and then stirred at room temperature for 24 hours. Then, the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography to obtain the desired compound (48 mg).

Example 13

Synthesis of pyridin-1-ium-1-yl(4-(4-(trifluoromethoxy)phenoxy)benzoyl)amide

[0303] ##STR00024##

[0304] 4-(4-(Trifluoromethoxy)phenoxy)benzoic acid (0.33 g) was dissolved in dichloromethane (5 mL), and then oxalyl chloride (0.15 g) and DMF (several drops) were added thereto, followed by stirring the mixture for 1.5 hours. The solvent was distilled off from the resultant under reduced pressure. The resultant was dissolved in dichloromethane (5 mL). 1-Aminopyridinium iodide (0.29 g) and triethylamine (0.13 g) were added thereto, followed by stirring the mixture at room temperature for 48 hours. Water was added to the resultant, and the mixture was subjected to extraction by ethyl acetate. An organic layer was concentrated under reduced pressure. The resultant concentrate was purified by silica gel column chromatography to obtain the desired compound (40 mg).

Example 14

Synthesis of pyridin-1-ium-1-yl(4-(4-(trifluoromethyl)benzyl)benzoyl)amide

[0305] ##STR00025##

[0306] 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaboran-2-yl)benzoic acid (12.4 g) was dissolved in dichloromethane (100 mL), and then oxalyl chloride (7.0 g) and DMF (several drops) were added thereto, followed by stirring the mixture for 1.5 hours. The solvent was distilled off from the resultant under reduced pressure. The resultant was dissolved in dichloromethane (150 mL). 1-Aminopyridinium iodide (12.2 g) and triethylamine (11.1 g) were added thereto, followed by stirring the mixture at room temperature for 16 hours. Then, an aqueous saturated sodium bicarbonate solution was added thereto. The precipitate was collected by filtration to obtain pyridin-1-ium-1-yl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)benzoyl)amide (0.43 g).

[0307] The resultant pyridin-1-ium-1-yl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)benzoyl)amide (0.26 g) was dissolved in N,N-dimethylformamide (3 mL) and water (1 mL). 1-(Bromomethyl)-4-(trifluoromethyl)benzene (0.23 g), potassium carbonate (0.17 g), and tetrakis(triphenylphosphine)palladium (92 mg) were added thereto, and then the mixture was stirred at 100° C. for 7.5 hours. Water was added thereto, and the mixture was subjected to extraction by ethyl acetate. An organic layer was concentrated under reduced pressure. The resultant concentrate was purified by silica gel column chromatography to obtain the desired compound (0.12 g).

Example 15

Synthesis of pyridin-1-ium-1-yl(4-((4-(trifluoromethoxy)phenoxy)methyl) benzoyl)amide

[0308] ##STR00026##

[0309] Methyl 4-((4-(trifluoromethoxy)phenoxy)methyl)benzoate (1.6 g) was dissolved in ethanol (15 mL), and then an aqueous solution of 4N sodium hydroxide (5 mL) was added thereto, followed by stirring the mixture at 60° C. for two hours. The resultant was neutralized with an aqueous solution of 4N hydrogen chloride. The precipitate was collected by filtration to obtain 4-((4-(trifluoromethoxy)phenoxy)methyl)benzoic acid (1.4 g).

[0310] The resultant 4-((4-(trifluoromethoxy)phenoxy)methyl)benzoic acid (0.31 g) was dissolved in dichloromethane (3 mL), and then oxalyl chloride (0.15 g) and DMF (one drop) were added thereto, followed by stirring the mixture for one hour. The solvent was distilled off from the resultant under reduced pressure, and the resultant was dissolved in dichloromethane (3 mL). 1-Aminopyridinium iodide (0.24 g) and triethylamine (0.24 g) were added thereto, followed by stirring the mixture at room temperature for 16 hours. Water was added thereto, and the mixture was subjected to extraction by ethyl acetate. An organic layer was concentrated under reduced pressure to obtain the desired compound (0.43 g).

Example 16

Synthesis of (4-((tert-butoxycarbonyl)amino)benzoyl)(pyridin-1-ium-1-yl)amide

[0311] ##STR00027##

[0312] 4-((Tert-butoxycarbonyl)amino)benzoic acid (5.0 g) was dissolved in dichloromethane (60 mL), and then 1-aminopyridinium iodide (5.1 g), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (4.8 g), 1-hydroxybenzotriazole hydrate (3.9 g), and triethylamine (5.1 g) were added thereto, followed by stirring the mixture at room temperature for 17 hours. Water was added thereto, and then the mixture was filtered. The resultant solid was washed with ethyl acetate to obtain the desired compound (6.2 g).

Example 17

Synthesis of 1-(4-aminobenzamide)pyridin-1-ium hydrochloride

[0313] ##STR00028##

[0314] (4-((Tert-butoxycarbonyl)amino)benzoyl)(pyridin-1-ium-1-yl)amide (3.1 g) was dissolved in dichloromethane (20 mL), and then trifluoroacetic acid (10 mL) was added thereto, followed by stirring the mixture at room temperature for 2.5 hours. The solvent was distilled off from the resultant under reduced pressure. The resultant residue was dissolved in methanol (10 mL), and then a 4N hydrochloric acid solution in dioxane (10 mL) was added thereto. The solvent was distilled off from the resultant under reduced pressure to obtain the desired compound (3.0 g).

Example 18

Synthesis of (4-((tert-butoxycarbonyl)(4-(trifluoromethoxy)benzyl)amino) benzoyl)(pyridin-1-ium-1-yl)amide

[0315] ##STR00029##

[0316] DMF (6 mL) was added to (4-((tert-butoxycarbonyl)amino)benzoyl)(pyridin-1-ium-1-yl)amide (0.31 g), and then sodium hydride (53 mg) was added thereto at 0° C., followed by stirring the mixture for 30 minutes. 1-(Bromomethyl)-4-(trifluoromethoxy)benzene (0.28 g) was added thereto, and stirred for one hour. Water was added thereto. The precipitate was collected by filtration to obtain the desired compound (0.49 g).

Example 19

Synthesis of 1-(4-((4-(trifluoromethoxy)benzyl)amino)benzamido)pyridin-1-ium hydrochloride

[0317] ##STR00030##

[0318] (4-((Tert-butoxycarbonyl)(4-(trifluoromethoxy)benzyl)amino)benzoyl)(pyridin-1-ium-1yl)amide (0.37 g) was dissolved in dichloromethane (3 mL), and then trifluoroacetic acid (1 mL) was added thereto, followed by stirring the mixture at room temperature for 18 hours. The solvent was distilled off from the resultant under reduced pressure. The resultant residue was dissolved in methanol (3 mL), and then a 4N hydrochloric acid solution in dioxane (1 mL) was added thereto. The solvent was distilled off from the resultant under reduced pressure to obtain the desired compound (0.36 g).

Example 20

Synthesis of pyridin-1-ium-1-yl(4-(4-(trifluoromethyl)benzamido)benzoyl)amide

[0319] ##STR00031##

[0320] 1-(4-Aminobenzamide)pyridin-1-ium hydrochloride (0.20 g) was dissolved in dichloromethane (3 mL), and then 4-(trifluoromethyl)benzoyl chloride (0.18 g) and triethylamine (0.25 g) were added thereto, followed by stirring the mixture at room temperature for 16.5 hours. Water was added thereto. The precipitate was collected by filtration. The resultant precipitate was washed with ethyl acetate to obtain the desired compound (0.23 g).

Example 21

Synthesis of pyridin-1-ium-1-yl(4-((4-(trifluoromethyl)phenyl)sulfonamido) benzoyl)amide

[0321] ##STR00032##

[0322] 1-(4-Aminobenzamide)pyridin-1-ium hydrochloride (0.20 g) was dissolved in dichloromethane (3 mL), and then 4-(trifluoromethyl)benzene sulfonyl chloride (0.21 g) and triethylamine (0.25 g) were added thereto, followed by stirring the mixture at room temperature for 16.5 hours. Water was added thereto. The precipitate was collected by filtration. The precipitate was washed with ethyl acetate to obtain the desired compound (0.15 g).

[0323] Some of the compounds according to the present invention produced in the same way as mentioned in the examples shown above are shown in Table 1. Among the compounds according to the present invention, compounds of formula (1) are indicated in Table 1. In formula (1), the number on the pyridine ring indicates the substitution position of X.sup.1, and the number on the benzene ring indicates the substitution position of X.sup.3. In Table 1, Me indicates a methyl group, Ph indicates a phenyl group, and Py indicates a pyridyl group. The physical property of each compound is shown in the column “physical property”. The property, refractive index (nD) or melting point (m.p.) is indicated as the physical property.

[0324] The NMR data of Compound C1-68 is shown below.

[0325] .sup.1H-NMR (CDCl.sub.3, δ ppm) 7.01 (m, 1H), 7.27 (t, 1H), 7.31 (t, 1H), 7.42 (t, 1H), 7.65 (t, 2H), 7.86 (t, 1H), 8.92 (t, 2H).

##STR00033##

TABLE-US-00001 TABLE 1 Compound Physical No. (X.sup.1)m A X.sup.2 (X.sup.3)n property C1-1 — O CONH—(4-CF.sub.3O—Ph) — m.p. 281-283° C. C1-2 — O CONH—CH.sub.2CH.sub.2CH.sub.2CH.sub.2SCF.sub.3 — m.p. 180-190° C. C1-3 — O CONH—CH.sub.2CH.sub.2CH.sub.2CF.sub.3 — m.p. 158-160° C. C1-4 — O CH═N—OCH.sub.2CF.sub.2CF.sub.3 — m.p. 139-141° C. C1-5 — O CH═N—OCH.sub.2CF.sub.3 — m.p. 142-143° C. C1-6 — O CH.sub.2—(4-CF.sub.3O—Ph) — m.p. 149-151° C. C1-7 — O CH.sub.2—(4-CF.sub.3—Ph) — m.p. 180-183° C. C1-8 — O O—(4-CF.sub.3O—Ph) — m.p. 111-113° C. C1-9 — O CH.sub.2—O—(4-CF.sub.3O—Ph) — m.p. 174-177° C. C1-10 — O O—CF.sub.2CFH—O—CF.sub.2CF.sub.2CF.sub.2OCF.sub.3 — m.p. 101-103° C. C1-11 — O O—CF.sub.2CFH—O—CF.sub.2CF.sub.2CF.sub.3 — m.p. 140-142° C. C1-12 — O O—CH.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2H — m.p. 118-120° C. C1-13 — O O—CH.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2H — m.p. 132-134° C. C1-14 — O O—CH.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.3 — m.p. 158-160° C. C1-15 — O O—CH.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.3 — m.p. 151-153° C. C1-16 — O O—CH.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.3 — m.p. 149-151° C. C1-17 — O S(═O)—CH.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.3 — m.p. 128-130° C. C1-18 — O S—CH.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.3 — m.p. 132-134° C. C1-19 — O O—CH.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.3 — m.p. 87-89° C. C1-20 — O O—CH.sub.2CF.sub.2CF.sub.2CF.sub.3 — m.p. 158-160° C. C1-21 — O O—CH.sub.2CF.sub.2CF.sub.3 — m.p. 180-182° C. C1-22 — O O—CH.sub.2CF.sub.3 — m.p. 140-142° C. C1-23 — O C═C—(4-CF.sub.3O—Ph) — m.p. 197-199° C. C1-24 — O O(5-CF.sub.3—Py-2-yl) — m.p. 174-176° C. C1-25 — O CH═CH—CF.sub.3 — m.p. 215-220° C. C1-26 — O C═C—CF.sub.3 — m.p. 182-186° C. C1-27 — O CH.sub.2—O(4-CF.sub.3—Ph) — m.p. 194-197° C. C1-28 — O SCF.sub.3 — m.p. 162-162.5° C. C1-29 — O C═C—(4-CF.sub.3—Ph) — m.p. 223-226° C. C1-30 — O CO(4-CF.sub.3O—Ph) — m.p. 125-128° C. C1-31 — O CH═CH—(4-CF.sub.3—Ph) — m.p. 250° C. C1-32 — O O—CH.sub.2(4-CF.sub.3—Ph) — m.p. 214-216° C. C1-33 — O O—CH.sub.2(4-Br—Ph) — m.p. 211-214° C. C1-34 — O O—CH.sub.2(4-CF.sub.3O—Ph) — m.p. 189-191° C. C1-35 — O CONHPh — m.p. 250° C. C1-36 — O CONMe.sub.2 — m.p. 199-201° C. C1-37 — O SO.sub.2Me — m.p. 228-230° C. C1-38 — O O—CH.sub.2—CH═CCl(Me) — m.p. 151-153° C. C1-39 — O O—CH.sub.2—C(Cl)═CHCl — m.p. 95-98° C. C1-40 — O O—CH.sub.2—C(Me)═CH.sub.2 — m.p. 105-108° C. C1-41 — O O—CH.sub.2—CH═C(Me).sub.2 — m.p. 120-122° C. C1-42 — O O—CH.sub.2—CCH — m.p. 103-106° C. C1-43 — O O—CH.sub.2—CH═CCl.sub.2 — m.p. 95-98° C. C1-44 — O O—CH.sub.2—CH═CH.sub.2 — m.p. 120-122° C. C1-45 — O OCH.sub.2Ph — m.p. 148-152° C. C1-46 — O CO.sub.2Me — m.p. 186-187° C. C1-47 — O O—(4-CF.sub.3—Ph) — m.p. 140-142° C. C1-48 — O O—(3-Cl—5-CF.sub.3—Py-2-yl) — m.p. 170-172° C. C1-49 — O OCF.sub.3 — m.p. 141-143° C. C1-50 — O NH—CONH—(2,4-Cl.sub.2—Ph) — m.p. 264-266° C. C1-51 — O NH—CSNH—(4-CF.sub.3—Ph) — m.p. 204-206° C. C1-52 — O N(Me)—CO—(4-CF.sub.3—Ph) — m.p. 208-209° C. C1-53 — O CH═N—NH—SO.sub.2—(4-Me—Ph) — m.p. 202-204° C. C1-54 — O NH—SO.sub.2—(4-CF.sub.3—Ph) — m.p. 199-203° C. C1-55 — O NH—CO—(4-CF.sub.3—Ph) — m.p. 287-289° C. C1-57 — O NH—CO.sub.2.sup.tBu — m.p. 251-253° C. C1-58 — O CH.sub.2CH.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.3 3-F m.p. 135-137° C. C1-59 — O CH═CHCF.sub.2CF.sub.2CF.sub.2CF.sub.3 3-F m.p. 160-165° C. C1-60 — O C(Me)═N—OCH.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.3 — m.p. 143-145° C. C1-61 — O C(Me)═N—OCH2CF2CF2CF3 — m.p. 133-135° C. C1-62 — O CH═N—OCH.sub.2CF.sub.2CFHCF.sub.3 3-F m.p. 87-89° C. C1-63 — O CH═N—OCH.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.3 3-F m.p. 96-98° C. C1-64 — O CH═N—OCH.sub.2CF.sub.2CF.sub.2CF.sub.3 3-F m.p. 110-112° C. C1-65 — O CH═N—OCH.sub.2CF.sub.2CF.sub.3 3-F m.p. 119-121° C. C1-66 — O O—CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2SCF.sub.3 3-F m.p. 91-93° C. C1-67 — O O—CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CF.sub.3 3-F m.p. 122-123° C. C1-68 — O O—CF.sub.2CFH—O—CF.sub.2CF(CF.sub.3)OCF.sub.2CF.sub.2CF.sub.3 3-F — C1-69 — O O—CH.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2H 3,5-F.sub.2 m.p. 151-153° C. C1-70 — O O—CH.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.3 3,5-F.sub.2 m.p. 166-168° C. C1-71 — O O—CH.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.3 3-Cl m.p. 166-168° C. C1-72 — O O—CH.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2H 3-Cl m.p. 155-157° C. C1-73 — O O—CH.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.3 3-Cl m.p. 176-178° C. C1-74 — O O—CF.sub.2CFH—O—CF.sub.2CF.sub.2CF.sub.2OCF.sub.3 3-F nD(22.1)1.6295 C1-75 — O O—CH.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2H 3-F m.p. 161-163° C. C1-76 — O O—CH.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.2CF.sub.3 3-F m.p. 172-174° C. C1-77 — O C═C—(4-CF.sub.3O—Ph) 3-Cl m.p. 154-156° C. C1-78 — O C═C—(4-CF.sub.3O—Ph) 3-F m.p. 140-142° C.

[0326] Additional examples of the compound according to the present invention prepared in the same way as mentioned above are shown in Table 2.

TABLE-US-00002 TABLE 2 Compound Physical No. Formula property C2-1 [00034] m.p. 93-95° C. C2-2 [00035] m.p. 162-164° C. C2-3 [00036] m.p. 140-144° C. C2-4 [00037] m.p. 161-165° C. C2-5 [00038] m.p. 241-243° C. C2-6 [00039] m.p. 123-125° C. C2-7 [00040] m.p. 101-104° C. C2-8 [00041] m.p. 161-162° C. C2-9 [00042] m.p. 183-184° C. C1-56 [00043] m.p. 204-206° C.

(Biological Test)

[0327] The following test examples show that the compound according to the present invention is useful as an active ingredient of a pest control agent. The term “part” is based on the mass.

(Preparation of Test Emulsion)

[0328] 5 parts by mass of a compound according to the present invention, 93.6 parts of dimethylformamide, and 1.4 parts of polyoxyethylene alkyl aryl ether were mixed and dissolved to obtain an emulsion (1) containing 5% by mass of the active ingredient.

(1) Efficacy Test (1) Against Mythimna separata Using Artificial Feed

[0329] 0.8 g of commercially-available artificial feed (Insect LFS, manufactured by Nosan Corporation) and 1 μl of the emulsion (I) were mixed well, and then 0.2 g of the mixture per treated area was packed into plastic test containers (each having a capacity of 1.4 ml) as test feeds.

[0330] Two second-instar larvae of Mythimna separata were left per treated area, and then the test containers were sealed with plastic covers. The test containers were placed in a thermostatic chamber at 25° C., and, after five days had passed therefrom, the mortality and the feed intake were measured. The test was repeated twice. In addition, the test was conducted under the same conditions as described above, except that the compound according to the present invention was removed from the emulsion (I), and evaluated as a solvent control area.

TABLE-US-00003 TABLE 3 Compound No. C1-4  C1-20 C2-2  C1-72 C1-9  C1-21 C2-4  C1-73 C1-10 Cl-23 C2-5 Cl-74 C1-11 C1-25 C1-62 C1-75 C1-12 C1-27 C1-64 C1-76 C1-13 C1-29 C1-65 C1-77 C1-14 C1-31 C1-68 C1-78 C1-15 C1-32 C1-69 C1-16 C1-34 C1-70 C1-19 C1-48 C1-71

[0331] The compounds shown in Table 3 were subjected to an efficacy test against Mythimna separata. All of the compounds caused 100% mortality of Mythimna separata or 10% or less of the feed intake, relative to the feed intake at the solvent control area, and thus the efficacy thereof against Mythimna separata was confirmed.

(2) Efficacy Test (2) Against Mythimna separata

[0332] The emulsion (1) was diluted with water such that the amount of the compound according to the present invention became 125 ppm by mass. A corn leaf disc was immersed in the diluted solution for 30 seconds. The corn leaf disc was put in a petri dish, and five second-instar larvae of Mythimna separata were left therein. The petri dish was placed in a thermostatic chamber at a temperature of 25° C. and a humidity of 60%. After six days had passed from leaving the larvae, life or death was assessed and the mortality was calculated. The test was repeated twice.

TABLE-US-00004 TABLE 4 Compound No. C1-27 C1-29 C1-31 C1-32 C1-33 C1-34 C1-47 C1-49 C2-4 

[0333] The compounds shown in Table 4 were subjected to an efficacy test against Mythimna separata. All of the compounds caused 80% or more mortality of Mythimna separata.

(3) Efficacy Test Against Spodoptera litura

[0334] The emulsion (1) was diluted with water such that the amount of the compound according to the present invention became 125 ppm by mass. A cabbage leaf disc was immersed in the diluted solution for 30 seconds. The cabbage leaf disc was air-dried and then put in a petri dish, followed by leaving five second-instar larvae of Spodoptera litura therein. The petri dish was placed in a thermostatic chamber at a temperature of 25° C. and a humidity of 60%. After six days had passed from leaving the larvae, life or death was assessed and the mortality was calculated. The test was repeated twice.

TABLE-US-00005 TABLE 5 Compound No. C1-6  C1-28 C2-5  C1-77 C1-10 Cl-29 Cl-58 C1-11 C1-31 C1-59 C1-12 C1-32 C1-63 C1-14 C1-34 C1-64 C1-15 C1-47 C1-69 C1-16 C1-48 C1-70 C1-19 C1-49 C1-74 C1-23 C2-1  C1-75 C1-25 C2-2  C1-76

[0335] The compounds shown in Table 5 were subjected to an efficacy test against Spodoptera litura. All of the compounds caused 80% or more mortality of Spodoptera litura.

(4) Efficacy Test Against Helicoverpa armigera

[0336] The emulsion (I) was diluted with water such that the amount of the compound according to the present invention became 125 ppm by mass. A cabbage leaf disc was immersed in the diluted solution for 30 seconds. The cabbage leaf disc was air-dried and then put in a petri dish, followed by leaving five second-instar larvae of Spodoptera litura therein. The petri dish was placed in a thermostatic chamber at a temperature of 25° C. and a humidity of 60%. After six days had passed from leaving the larvae, life or death was assessed and the mortality was calculated. The test was repeated twice.

TABLE-US-00006 TABLE 6 Compound No. C1-10 C1-11 C1-15 C1-23 C2-1  C2-2  C1-60 C1-61 C1-63 C1-64

[0337] The compounds shown in Table 6 were subjected to an efficacy test against Helicoverpa armigera. All of the compounds caused 80% or more mortality of Helicoverpa armigera.

(5) Efficacy Test Against Plutella xylostella

[0338] The emulsion (I) was diluted with water such that the amount of the compound according to the present invention became 125 ppm by mass. A cabbage leaf disc was immersed in the diluted solution for 30 seconds. The cabbage leaf disc was air-dried and then put in a petri dish, followed by leaving five second-instar larvae of Spodoptera litura therein. The petri dish was placed in a thermostatic chamber at a temperature of 25° C. and a humidity of 60%. After three days had passed from leaving the larvae, life or death was assessed and the mortality was calculated. The test was repeated twice.

TABLE-US-00007 TABLE 7 Compound No. C1-27 C1-29 C1-30 C1-31 C1-32 C1-33 C1-49 C2-5 

[0339] The compounds shown in Table 7 were subjected to an efficacy test against Plutella xylostella. All of the compounds caused 80% or more mortality of Plutella xylostella.

(6) Efficacy Test Against Tetranychus kanzawai

[0340] Five female adults of Tetranychus kanzawai were left on primary leaves of mung bean planted in a 3-sun pot. The emulsion (I) was diluted with water such that the amount of the compound according to the present invention became 125 ppm by mass. The diluted solution was sprayed on the mung bean and evaluated as a treated area. In addition, the test was conducted under the same conditions as described above, except that the compound according to the present invention was removed from the emulsion (I), and evaluated as a solvent control area. The 3-sun pot was placed in a thermostatic chamber at a temperature of 25° C. and a humidity of 65%, and after four days had passed from spraying, the female adults of Tetranychus kanzawai were removed to leave only laid eggs remaining on the leaves. After eleven days had passed from spraying, the number of living Tetranychus kanzawai was counted and the control ratio was calculated in accordance with the following formula. The test was repeated twice.

Control ratio (%)=100×[1−Nt/Nc]

[0341] Nt is the living number at the treated area, and Nc is the living number at the solvent control area.

TABLE-US-00008 TABLE 8 Compound No. C1-4  C2-3  C1-77 C1-6  C1-62 C1-78 C1-7  C1-63 C1-8  C1-64 C1-9  C1-65 C1-10 C1-66 C1-11 C1-67 C1-18 C1-68 C1-23 C1-73 C2-2  C1-74

[0342] The compounds shown in Table 8 were subjected to an efficacy test against Tetranychus kanzawai. All of the compounds exhibited 90% or more control ratio.

(7) Efficacy Test Against Tetranychus urticae

[0343] Five female adults of Tetranychus urticae were left on primary leaves of kidney bean planted in a 3-sun pot. The emulsion (I) was diluted with water such that the amount of the compound according to the present invention became 125 ppm by mass. The diluted solution was sprayed on the kidney bean and evaluated as a treated area. In addition, the test was conducted under the same conditions as described above, except that the compound according to the present invention was removed from the emulsion (1), and evaluated as a solvent control area. The 3-sun pot was placed in a thermostatic chamber at a temperature of 25° C. and a humidity of 65%, and after three days had passed from spraying, the female adults of Tetranychus urticae were removed to leave only laid eggs remaining on the leaves. After ten days had passed from spraying, the number of living Tetranychus urticae was counted and the control ratio was calculated in accordance with the following formula. The test was repeated twice.

Control ratio (%)=100×[1−Nt/Nc]

[0344] Nt is the living number at the treated area, and Nc is the living number at the solvent control area.

TABLE-US-00009 TABLE 9 Compound No. C1-24 C2-4 C1-27 C2-5 C1-28 C2-6 C1-29 C1-34 C1-37 C1-47 C1-48 C1-49 C2-3 

[0345] The compounds shown in Table 9 were subjected to an efficacy test against Tetranychus urticae. All of the compounds exhibited 90% or more control ratio.

(8) Efficacy Test Against Aphis gossypii

[0346] Cucumber was sown in a 3-sun pot. After ten days had passed from germination, a female adult of Aphis gossypii was left on the cucumber. On the next day, laid first-instar larvae were left, and the female adult was removed. The emulsion (I) was diluted with water such that the amount of the compound according to the present invention became 125 ppm by mass. The diluted solution was sprayed on the cucumber. Then, the cucumber was placed in a thermostatic chamber at a temperature of 25° C. and a humidity of 60%. After five days had passed therefrom, life or death of Aphis gossypii was assessed and the mortality was calculated.

[0347] Compounds C-63 and C-74 were subjected to an efficacy test against Aphis gossypii. Both of the compounds caused 80% or more mortality.

(9) Efficacy Test Against Nilaparvata lugens

[0348] The emulsion (I) was diluted with water such that the amount of the compound according to the present invention became 125 ppm by mass. A rice seedling was immersed in the diluted solution for 30 seconds, air-dried, and then placed in a plastic case, followed by leaving five second-instar larvae of Nilaparvata lugens therein. The plastic case was placed in a thermostatic chamber at a temperature of 25° C. and a humidity of 65%. After ten days had passed therefrom, life or death was assessed and the mortality was calculated using the following formula. The test was repeated twice.

Mortality (%)=(the number of dead insects/the number of supplied insects)×100

[0349] Compounds C-63, C-64 and C-65 were subjected to an efficacy test against Nilaparvata lugens. All of the compounds caused 80% or more mortality.

[0350] Since the compounds randomly selected from the pyridinium salts according to the present invention exhibited the above-described effects, it is understood that the pyridinium salt according to the present invention, involving aspects of the compound that are not shown in the above examples, is a compound that exhibits pest control effects, acaricidal effects, and particularly insecticidal effects.

INDUSTRIAL APPLICABILITY

[0351] The pyridinium salt according to the present invention has control activity against pests that cause problems to agricultural crops or in the health field. The control agent containing the pyridinium salt according to the present invention can effectively control pests, particularly agricultural insect pests and acarians, at low doses, and can further effectively control ectoparasites and endoparasites that may harm humans and animals.