TW202110804A - Pyridinium salt and pest control agent - Google Patents

Abstract

A compound represented by formula (I) or formula (II) (in the formulas, A represents an oxygen atom or a sulfur atom, X1 represents a halogeno group or a substituted or unsubstituted C1-6 alkyl group, etc., m represents a number of X1 and is any integer of 0-5, Y represents a substituted or unsubstituted C1-6 alkylene group, etc., X2 represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, etc., X3 represents a halogeno group, substituted or unsubstituted C1-6 alkyl group, hydroxyl group, etc., n represents a number of X3 and is any integer of 0-4, Zq- represents a counterion, and q represents the valence of the counterion and is 1 or 2.).

Description

Pyridinium salt and pest control agent

The present invention relates to a pyridinium salt and a pest control agent. More specifically, the present invention relates to a pyridinium salt having excellent insecticidal activity and/or acaricidal activity, excellent safety, and industrially advantageous synthesis, and a pest control agent containing it as an effective ingredient .

A variety of compounds with insecticidal/acaricidal activity are proposed. In order to use such compounds as pesticides, it is required not only to be sufficiently effective, but also to be resistant to pesticides, not to cause phytotoxicity to plants or soil pollution, and to have low toxicity to livestock, fish, etc.

However, Patent Document 1 discloses a compound represented by formula (A) having acaricidal activity and the like. [化1]

[現有技術文獻] [專利文獻]In addition, Non-Patent Document 1 discloses a compound represented by formula (B) and the like having analgesic activity. [化2]

[Prior Art Document] [Patent Document]

[Patent Document 1] US Patent No. 4138548 [Non-Patent Literature]

[Non-Patent Document 1] Journal of Medicinal Chemistry, 1982, vol. 25, p720-723

[The problem to be solved by the invention] The subject of the present invention is to provide a pyridinium salt that has pest control activity, especially insecticidal activity and/or acaricidal activity, is excellent in safety, and can be advantageously synthesized industrially. Another subject of the present invention is to provide a pest control agent, insecticide or acaricide, external parasite control agent, or internal parasite control or repellent containing a pyridinium salt as an active ingredient. [Means to solve the problem]

In order to solve the above-mentioned problems, studies have been conducted, and as a result, the present invention including the following aspects has been completed. [1] A compound represented by formula (I) or formula (II).

[化4]

[化3]

[化4]

(In formula (I) and formula (II), A represents an oxygen atom or a sulfur atom, X ¹ represents a halogen group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkene Group, substituted or unsubstituted C2-6 alkynyl, substituted or unsubstituted C1-6 alkoxy, substituted or unsubstituted C2-6 alkenyloxy, substituted or unsubstituted C2-6 alkynyloxy, substituted or unsubstituted C1-6 alkylcarbonyl, substituted or unsubstituted C1-6 alkoxycarbonyl, substituted or unsubstituted C1-6 alkylthio, A substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C3-8 cycloalkyl group, Unsubstituted C6-10 aryl groups, substituted or unsubstituted C6-10 aryloxy groups, substituted or unsubstituted 5- to 6-membered heteroaryl groups, substituted or unsubstituted 5-membered to 6-membered heteroaryloxy group, group represented by ^Ra R ^b N-, group represented by ^Ra R ^b N-CO-, group represented by R ^c CO-NH-, pentafluoro Hydrosulfide, nitro or cyano, R ^a represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R ^b represents a hydrogen atom, A substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R ^c represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C1-6 alkyl group A substituted C6-10 aryl group, m represents ^{the number of X 1} and is any integer of 0-5, Y represents a substituted or unsubstituted C1-6 alkylene group, and a substituted or unsubstituted C2- 6 alkynylene or substituted or unsubstituted C3-6 cycloalkylene, X ² represents substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl, Substituted or unsubstituted C2-6 alkynyl, hydroxyl, substituted or unsubstituted C1-6 alkoxy, substituted or unsubstituted C2-6 alkenyloxy, substituted or unsubstituted C2-6 alkynyloxy, substituted or unsubstituted C1-6 alkylcarbonyl, substituted or unsubstituted C1-6 alkoxycarbonyl, substituted or unsubstituted C1-6 alkylthio, A substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C3-8 cycloalkyl group, Unsubstituted C6-10 aryl groups, substituted or unsubstituted C6-10 aryloxy groups, substituted or unsubstituted 5- to 6-membered heteroaryl groups, substituted or unsubstituted 5-membered to 6-membered heteroaryloxy group, group ^{represented by R a1} R ^b1 N-, group represented by R ^a1 R ^b1 N-CO-, group represented by R ^c1 CO-NH-, pentafluoro Hydrosulfide, nitro or cyano, R ^a1 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R ^b1 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R ^c1 represents a hydrogen atom, substituted or unsubstituted A substituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, X ³ represents a halogen group, a substituted or unsubstituted C1-6 alkyl group, a hydroxy group, a substituted or unsubstituted C1-6 alkoxy, substituted or unsubstituted C1-6 alkylthio, substituted or unsubstituted C1-6 alkylsulfinyl, substituted or unsubstituted C1-6 alkyl Sulfonyl, pentafluorohydrosulfide, nitro or cyano, n represents ^{the number of X 3} and is any integer from 0 to 4, Z ^q- represents a counter ion, and q represents the valence of the counter ion and is 1 or 2)

[2] A pest control agent containing at least one selected from the compounds described in [1] as an active ingredient. [3] An insecticide or acaricide containing at least one selected from the compounds described in [1] as an active ingredient. [4] An ectoparasite control agent containing at least one selected from the compounds described in [1] as an active ingredient. [5] An internal parasite control or repellent containing at least one selected from the compounds described in [1] as an active ingredient. [Effects of the invention]

The pyridinium salt of the present invention has a function of controlling harmful organisms that are a problem in crops or hygiene. The control agent containing the pyridinium salt of the present invention can effectively control harmful organisms, especially agricultural pests and mites at a lower concentration, and can effectively control external parasites and internal parasites that sometimes harm humans and animals.

[化6]

The pyridinium salt of the present invention is a compound (intramolecular salt) represented by formula (I) or a compound (intermolecular salt) represented by formula (II). Intramolecular salts are compounds that have a cationic center and an anionic center in one molecule, that is, zwitterions. Intermolecular salts are compounds formed by ion association between cations and anions, that is, ion pairs. [化5]

[化6]

Here, the term "unsubstituted" refers to only the base that becomes the parent nucleus. When there is no description of "substitution" and only the name of the base that becomes the core is described, it means "unsubstituted" unless otherwise specified. On the other hand, the term "substituted" means that any hydrogen atom of the group that becomes the parent nucleus is replaced by a group (substituent) having the same or different structure from the parent nucleus. Therefore, the "substituent" is another group that is bonded to the group that becomes the core. The substituent may be one or two or more. Two or more substituents may be the same or different. Terms such as "C1 to 6" indicate that the number of carbon atoms of the group forming the core is 1 to 6, and so on. The number of carbon atoms does not include the number of carbon atoms present in the substituent. For example, a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group.

The "substituent" is not particularly limited as long as it is chemically acceptable and has the effect of the present invention. Examples of groups that can become "substituents" are shown below. C1-6 alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, second butyl, isobutyl, tertiary butyl, n-pentyl, n-hexyl, etc.; Vinyl, 1-propenyl, 2-propenyl (allyl), 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl -2-propenyl and other C2～6 alkenyl groups; C2-6 alkynyl groups such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, etc.;

Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cubanyl group and other C3-8 cycloalkyl groups; C6-10 aryl groups such as phenyl and naphthyl; C6-10 aryl C1-6 alkyl groups such as benzyl and phenethyl groups; 3-membered to 6-membered heterocyclic group; 3-membered to 6-membered heterocyclic group C1-6 alkyl;

Hydroxyl C1~6 alkoxy groups such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, second butoxy, isobutoxy, and tertiary butoxy; C2-6 alkenyloxy groups such as vinyloxy, allyloxy, propyleneoxy, butenoxy; C2-6 alkynyloxy groups such as ethynyloxy and propargyloxy; C6-10 aryloxy groups such as phenoxy and naphthoxy; C6～10 aryl C1～6 alkoxy groups such as benzyloxy and phenethoxy; 5- to 6-membered heteroaryloxy groups such as thiazolyloxy and pyridyloxy; 5- to 6-membered heteroaryl C1-6 alkoxy groups such as thiazolylmethoxy and pyridylmethoxy;

Formaldehyde C1-6 alkylcarbonyl groups such as acetyl and propyl; Formyloxy C1-6 alkylcarbonyloxy groups such as acetoxy and propoxy; C6～10 arylcarbonyl groups such as benzyl; C1~6 alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, and tertiary butoxycarbonyl; Methoxycarbonyloxy, ethoxycarbonyloxy, n-propoxycarbonyloxy, isopropoxycarbonyloxy, n-butoxycarbonyloxy, tertiary butoxycarbonyloxy, etc. C1～6 Alkoxycarbonyloxy; carboxyl;

Halogen groups such as fluoro, chloro, bromo, and iodo; C1～6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, 1-fluoro-n-butyl, etc.; C2～6 haloalkenyl groups such as 2-chloro-1-propenyl and 2-fluoro-1-butenyl; 4,4-Dichloro-1-butynyl, 4-fluoro-1-pentynyl, 5-bromo-2-pentynyl and other C2-6 haloalkynyl groups; C1～6 halogenated alkoxy groups such as trifluoromethoxy, 2-chloro-n-propoxy and 2,3-dichlorobutoxy; C2-6 haloalkenyloxy groups such as 2-chloropropenoxy and 3-bromobutenyloxy; C1～6 haloalkylcarbonyl groups such as chloroacetoxy, trifluoroacetoxy, and trichloroacetoxy;

Amine group C1-6 alkyl substituted amino groups such as methylamino, dimethylamino, and diethylamino; C6-10 arylamino groups such as anilino and naphthylamino groups; C6-10 aryl C1-6 alkylamino groups such as benzylamino group and phenethylamino group; Methylamino group; C1-6 alkylcarbonylamino groups such as acetylamino, propionylamino, butyrylamino, isopropylcarbonylamino, etc.; C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, isopropoxycarbonylamino group, etc.; Unsubstituted or substituted aminocarbonyl groups such as aminocarbonyl, dimethylaminocarbonyl, phenylaminocarbonyl, N-phenyl-N-methylaminocarbonyl, etc.; C1-6 alkyl groups such as iminomethyl, (1-imino)ethyl, (1-imino)n-propyl, etc.; N-hydroxy-iminomethyl, (1-(N-hydroxy)-imino)ethyl, (1-(N-hydroxy)-imino)propyl, N-methoxy-imine Substituted or unsubstituted N-hydroxyimino C1-6 alkyl groups such as methyl, (1-(N-methoxy)-imino)ethyl, etc.; Aminocarbonyloxy; C1-6 alkyl substituted aminocarbonyloxy groups such as ethylaminocarbonyloxy and dimethylaminocarbonyloxy;

Sulfhydryl C1-6 alkylthio groups such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, second butylthio, third butylthio, etc.; C1～6 halogenated alkylthio groups such as trifluoromethylthio and 2,2,2-trifluoroethylthio; C6-10 arylthio groups such as phenylthio and naphthylthio; 5- to 6-membered heteroarylthio groups such as thiazolylthio and pyridinethio;

C1-6 alkylsulfinyl groups such as methylsulfinyl, ethylsulfinyl and tertiary butylsulfinyl; C1~6 halogenated alkylsulfinyl groups such as trifluoromethylsulfinyl and 2,2,2-trifluoroethylsulfinyl; C6-10 arylsulfinyl groups such as phenylsulfinyl group; 5- to 6-membered heteroarylsulfinyl groups such as thiazolylsulfinyl and pyridylsulfinyl;

C1-6 alkylsulfonyl groups such as methylsulfonyl, ethylsulfonyl and tertiary butylsulfonyl; Trifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl and other C1-6 haloalkylsulfonyl groups; C6-10 arylsulfonyl groups such as phenylsulfonyl; 5- to 6-membered heteroarylsulfonyl groups such as thiazolylsulfonyl and pyridylsulfonyl; C1-6 alkylsulfonyloxy groups such as methylsulfonyloxy, ethylsulfonyloxy and tertiary butylsulfonyloxy; Trifluoromethylsulfonyloxy, 2,2,2-trifluoroethylsulfonyloxy and other C1-6 haloalkylsulfonyloxy groups;

Trimethylsilyl, triethylsilyl, tertiary butyldimethylsilyl and other tri-C1-6 alkyl substituted silyl groups; Triphenylsilyl and other tri-C6-10 aryl substituted silyl groups; Pentafluorohydrosulfide; Cyano; nitro.

In addition, regarding these "substituents", any hydrogen atom in the substituents may be substituted by groups of different structures. As the "substituent" in this case, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a halogen group, a cyano group, a nitro group, etc. may be mentioned.

In addition, the "3-membered to 6-membered heterocyclic group" includes one to four heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as the constituent atoms of the ring. The heterocyclic group may be either monocyclic or polycyclic. Regarding the polycyclic heterocyclic group, as long as at least one ring is a heterocyclic ring, the remaining ring may be any of a saturated alicyclic ring, an unsaturated aliphatic ring, or an aromatic ring. Examples of "3-membered to 6-membered heterocyclic group" include: 3-membered to 6-membered saturated heterocyclic group, 5-membered to 6-membered heteroaryl group, 5-membered to 6-membered ring The partially unsaturated heterocyclic group and so on.

Examples of the saturated heterocyclic group of 3- to 6-membered ring include: aziridinyl, epoxy, pyrrolidinyl, tetrahydrofuranyl, tetrahydrothiazolyl, piperidinyl, piperazinyl, morpholinyl, Dioxolane, dioxanyl, etc.

Examples of 5-membered heteroaryl groups include: pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiene Azolyl, thiadiazolyl, tetrazolyl, etc. Examples of 6-membered heteroaryl groups include pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl.

[Z ^q- ] In the formula (II), Z ^q- represents a counter ion, and q represents the valence of the counter ion and is 1 or 2. Examples of the monovalent anion Z ^- Specific examples ^{include: Cl -, Br -, I} -, NO 3 -, CH 3 COO -, CH 3 SO 3 -, CF 3 SO 3 -, TolSO 3 - and the like. As a specific example of the divalent anion Z ^2- _{, SO 4} ^2- and the like can be cited. Tol is an abbreviation for o-methylphenyl, m-methylphenyl, or p-methylphenyl.

[A] In formula (I) and formula (II), A represents an oxygen atom or a sulfur atom. In the present invention, A is preferably an oxygen atom.

[X ¹ , m] In formula (I) and formula (II), X ¹ represents a halogen group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a Substituted or unsubstituted C2-6 alkynyl, substituted or unsubstituted C1-6 alkoxy, substituted or unsubstituted C2-6 alkenyloxy, substituted or unsubstituted C2-6 Alkynyloxy, substituted or unsubstituted C1-6 alkylcarbonyl, substituted or unsubstituted C1-6 alkoxycarbonyl, substituted or unsubstituted C1-6 alkylthio, substituted or Unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C3-8 cycloalkyl group, substituted or unsubstituted C6-10 aryl groups, substituted or unsubstituted C6-10 aryloxy groups, substituted or unsubstituted 5- to 6-membered heteroaryl groups, substituted or unsubstituted 5-membered rings ～6-membered heteroaryloxy group, group represented by ^Ra R ^b N-, group represented by ^Ra R ^b N-CO-, group represented by R ^c CO-NH-, pentafluorohydrosulfide group , Nitro or cyano, m represents ^{the number of X 1} and is any integer of 0-5, preferably any integer of 0-2, more preferably 0. When m is 2 or more, X ¹ may be the same or different from each other.

Examples of the "halo group" in X ¹ include a fluoro group, a chloro group, a bromo group, and an iodo group.

The "C1-6 alkyl group" in X ¹ may be a straight chain or a branched chain. Examples of the "C1-6 alkyl group" in X ¹ include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, isopropyl, isobutyl, sec-butyl, Tertiary butyl, isopentyl, neopentyl, 2-methylbutyl, 2,2-dimethylpropyl, isohexyl, etc.

Examples of "C2-6 alkenyl" in X ¹ include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl 2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butene Group, 2-methyl-2-butenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, etc.

-甲基-2-丁炔基、2-甲基-3-戊炔基、1-己炔基、1,1-二甲基-2-丁炔基等。Examples of "C2-6 alkynyl" in X ¹ include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1 -Methyl-2-propynyl, 2-methyl-3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1

-Methyl-2-butynyl, 2-methyl-3-pentynyl, 1-hexynyl, 1,1-dimethyl-2-butynyl, etc.

Examples of the "C1-6 alkoxy group" in X ¹ include: methoxy, ethoxy, n-propoxy, n-butoxy, n-pentoxy, n-hexoxy, isopropoxy, and isopropyloxy. Butoxy, second butoxy, tertiary butoxy, isohexoxy, etc.

As X ¹ "C2 ~ 6 alkenyl groups" include: vinyloxy, allyloxy, propenyloxy, butenyloxy and the like.

X ¹ is of "C2 ~ 6 alkynyl group" include ethynyl group, propynyl group and the like.

As of ¹ X 'C1 ~ 6 alkylcarbonyl group "include acetyl group, propionyl, acyl and the like.

X ¹ as "C1 ~ 6 alkoxycarbonyl group" include: methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl group, isopropoxycarbonyl group, tertiary butoxycarbonyl group and the like.

Examples of the "C1-6 alkylthio group" in X ¹ include methylthio, ethylthio, n-propylthio, n-butylthio, n-pentylthio, n-hexylthio, isopropylthio, and the like.

X ¹ as "C1 ~ 6 alkylsulfinyl acyl" include: acyl methylsulfinyl, B alkylsulfinyl acyl, acyl third butylsulfinamide like.

As of ¹ X 'C1 ~ 6 alkylsulfonyl group "include: acyl sulfo methyl, ethyl, sulfo acyl, sulfo acyl tert-butyl and the like.

As the "C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkoxy group", "C2-6 alkenyloxy group", "C2～6 alkenyl group" in ^{X 1} 6 alkynyloxy", "C1-6 alkylcarbonyl", "C1-6 alkoxycarbonyl", "C1-6 alkylthio", "C1-6 alkylsulfinyl" or "C1-6 The substituents on the "alkylsulfonyl" are preferably: halogen groups such as fluoro, chloro, bromo, and iodo; hydroxyl; methoxy, ethoxy, n-propoxy, isopropoxy, C1～6 alkoxy groups such as n-butoxy, second butoxy, isobutoxy, and tertiary butoxy; 2-chloro-n-propoxy, 2,3-dichlorobutoxy, trifluoromethyl C1-6 haloalkoxy such as oxy; C6-10 aryl such as phenyl and naphthyl; or cyano.

X ¹ is the "C3 ~ 8 cycloalkyl group" include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and the like.

Examples of the "C6-10 aryl group" in X ¹ include a phenyl group, a naphthyl group, and the like.

Examples of the "C6-10 aryloxy group" in X ^{1 include phenoxy and naphthoxy.}

The "5-membered to 6-membered heteroaryl group" in X ¹ includes one, two, three, or four heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as a ring The constituent atoms. When there are two or more heteroatoms, these may be the same or different. Examples of 5-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, and oxadiazole Group, thiadiazolyl, tetrazolyl, etc., as the 6-membered heteroaryl group, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, etc. can be mentioned.

The "5-membered to 6-membered heteroaryloxy group" in X ¹ has a structure in which a 5- to 6-membered heteroaryl group is bonded to an oxy group. As a specific example, a thiazolyloxy group, a pyridyloxy group, etc. are mentioned.

As the "C3-8 cycloalkyl group", "C6-10 aryl group", "C6-10 aryloxy group", "5-membered to 6-membered heteroaryl group" or "5-membered ring-" in ^{X 1} The substituents on the "6-membered ring heteroaryloxy" are preferably: halo groups such as fluoro, chloro, bromo, iodo; methyl, ethyl, n-propyl, isopropyl, n-butyl , Second butyl, isobutyl, tertiary butyl, n-pentyl, n-hexyl and other C1-6 alkyl groups; chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl , 1-fluoro n-butyl and other C1~6 haloalkyl groups; hydroxy; methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, second butoxy, isobutoxy, C1-6 alkoxy such as tertiary butoxy; C1-6 haloalkoxy such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, trifluoromethoxy, etc.; or cyano.

In the " ^{group represented by R a} R ^b N-" or "group represented by R ^a R ^b N-CO-" in X ^{1 , R a} represents a hydrogen atom, a substituted or unsubstituted C1-6 alkane A group or a substituted or unsubstituted C6-10 aryl group, and R ^b represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. The "C1-6 alkyl group" in R ^a or R ^b may be a straight chain or a branched chain. Examples of the "C1-6 alkyl group" in R ^a or R ^b include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, isopropyl, isobutyl, and second Butyl, tertiary butyl, isopentyl, neopentyl, 2-methylbutyl, 2,2-dimethylpropyl, isohexyl, etc. As the substituent on the "C1-6 alkyl", preferred are halogen groups such as fluoro, chloro, bromo, and iodo; hydroxyl; methoxy, ethoxy, n-propoxy, isopropoxy Group, n-butoxy, second butoxy, isobutoxy, tertiary butoxy and other C1-6 alkoxy; 2-chloro-n-propoxy, 2,3-dichlorobutoxy, tri C1-6 haloalkoxy such as fluoromethoxy; C6-10 aryl groups such as phenyl and naphthyl; or cyano.

Examples of the "C6-10 aryl group" in R ^a or R ^{b include phenyl and naphthyl.} As the substituent on the "C6-10 aryl", preferred are halogen groups such as fluoro, chloro, bromo, and iodo; methyl, ethyl, n-propyl, isopropyl, n-butyl, C1~6 alkyl groups such as second butyl, isobutyl, tertiary butyl, n-pentyl, n-hexyl; chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, C1～6 haloalkyl groups such as 1-fluoro n-butyl; hydroxy; methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, second butoxy, isobutoxy, first C1-6 alkoxy such as tributoxy; C1-6 haloalkoxy such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, trifluoromethoxy; or cyano.

In the " ^{group represented by R c} CO-NH-" in X ^{1 , R c} represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group . The "C1-6 alkyl group" in R ^c may be a straight chain or a branched chain. Examples of the "C1-6 alkyl group" in R ^c include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, isopropyl, isobutyl, sec-butyl, Tertiary butyl, isopentyl, neopentyl, 2-methylbutyl, 2,2-dimethylpropyl, isohexyl, etc. As the substituent on the "C1-6 alkyl", preferred are halogen groups such as fluoro, chloro, bromo, and iodo; hydroxyl; methoxy, ethoxy, n-propoxy, isopropoxy Group, n-butoxy, second butoxy, isobutoxy, tertiary butoxy and other C1-6 alkoxy; 2-chloro-n-propoxy, 2,3-dichlorobutoxy, tri C1-6 haloalkoxy such as fluoromethoxy; C6-10 aryl groups such as phenyl and naphthyl; or cyano.

Examples of the "C6-10 aryl group" in R ^{c include a phenyl group and a naphthyl group.} As the substituent on the "C6-10 aryl", preferred are halogen groups such as fluoro, chloro, bromo, and iodo; methyl, ethyl, n-propyl, isopropyl, n-butyl, C1~6 alkyl groups such as second butyl, isobutyl, tertiary butyl, n-pentyl, n-hexyl; chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, C1～6 haloalkyl groups such as 1-fluoro n-butyl; hydroxy; methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, second butoxy, isobutoxy, first C1-6 alkoxy such as tributoxy; C1-6 haloalkoxy such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, trifluoromethoxy; or cyano.

In the present invention, X ^{1 is} preferably a halogen group, a halogen-substituted or unsubstituted C1-6 alkyl group, or a halogen-substituted or unsubstituted C1-6 alkoxy group.

Examples of the "halo-substituted C1-6 alkyl group" in X ^{1 include difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 2,2,2,1,1} -Pentafluoroethyl, etc. Examples of the "halo-substituted C1-6 alkoxy group" in X ^{1 include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-tri} Fluoroethoxy, 2,2,1,1-tetrafluoroethoxy, 2,2,2,1,1-pentafluoroethoxy, etc.

[Y] Y represents a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkynylene group, or a substituted or unsubstituted C3-6 cycloalkylene group. Among them, a substituted or unsubstituted C1-6 alkylene group is preferred. Examples of the "C1-6 alkylene group" in Y include a methylene group, a dimethylene group, a trimethylene group, and a tetramethylene group. Among them, dimethylene is preferred. Examples of "C2-6 alkynylene" in Y include ethynylene (-C≡C-), propynylene (-CH ₂ -C≡C-, -C≡C-CH ₂ -), etc. . Among them, ethynylene (-C≡C-) is preferred. Examples of "C3-6 cycloalkylene" in Y include: 1,2-cycloalkylene, 1,2-cyclobutylene, 1,3-cyclobutylene, and 1,2-cyclobutylene Pentyl, 1,3-cyclopentyl, 1,2-cyclohexyl, 1,3-cyclohexyl, 1,4-cyclohexyl, etc. Among them, 1,2-cycloalkylene is preferred. The substituents on the "C1-6 alkylene", "C2-6 alkynylene" or "C3-6 cycloalkylene" in Y are preferably: fluoro, chloro, bromo, and iodine Halo groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, second butyl, isobutyl, tertiary butyl and other C1-6 alkyl groups; chloromethyl, chloroethyl , Trifluoromethyl, 1,2-dichloro-n-propyl, 1-fluoro-n-butyl and other C1～6 haloalkyl groups; methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy Group, second butoxy, isobutoxy, tertiary butoxy and other C1-6 alkoxy; 2-chloro-n-propoxy, 2,3-dichlorobutoxy, trifluoromethoxy, etc. C1～6 halogenated alkoxy; methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, second butylthio, third butylthio, etc. C1～6 Alkylthio; methylsulfinyl, ethylsulfinyl, tertiary butylsulfinyl and other C1-6 alkylsulfinyl groups; or methylsulfinyl, ethylsulfinyl, C1-6 alkylsulfonyl groups such as the tertiary butylsulfonyl group. Among them, a halogen group or a C1-6 alkyl group is preferred.

[X ² ] X ² represents substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl, substituted or unsubstituted C2-6 alkynyl, hydroxyl, substituted Or unsubstituted C1~6 alkoxy, substituted or unsubstituted C2~6 alkenyloxy, substituted or unsubstituted C2~6 alkynyloxy, substituted or unsubstituted C1~6 Alkylcarbonyl, substituted or unsubstituted C1-6 alkoxycarbonyl, substituted or unsubstituted C1-6 alkylthio, substituted or unsubstituted C1-6 alkylsulfinyl, Substituted or unsubstituted C1-6 alkylsulfonyl, substituted or unsubstituted C3-8 cycloalkyl, substituted or unsubstituted C6-10 aryl, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted 5- to 6-membered heteroaryl group, substituted or unsubstituted 5- to 6-membered heteroaryloxy group, R ^a1 R ^b1 A group represented by N-, a group represented by R ^a1 R ^b1 N-CO-, a group represented by R ^c1 CO-NH-, a pentafluorohydrothio group, a nitro group, or a cyano group.

In the " ^{group represented by R a1} R ^b1 N-" or "group represented by R ^a1 R ^b1 N-CO-" in X ^{2 , R a1} represents a hydrogen atom, a substituted or unsubstituted C1-6 alkane A group or a substituted or unsubstituted C6-10 aryl group, and R ^b1 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. The "C1-6 alkyl group" in R ^a1 or R ^b1 may be a straight chain or a branched chain. Examples of the "C1-6 alkyl group" in R ^a1 or R ^b1 include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, isopropyl, isobutyl, and second Butyl, tertiary butyl, isopentyl, neopentyl, 2-methylbutyl, 2,2-dimethylpropyl, isohexyl, etc. As the substituent on the "C1-6 alkyl", preferred are halogen groups such as fluoro, chloro, bromo, and iodo; hydroxyl; methoxy, ethoxy, n-propoxy, isopropoxy Group, n-butoxy, second butoxy, isobutoxy, tertiary butoxy and other C1-6 alkoxy; 2-chloro-n-propoxy, 2,3-dichlorobutoxy, tri C1-6 haloalkoxy such as fluoromethoxy; C6-10 aryl groups such as phenyl and naphthyl; or cyano.

Examples of the "C6-10 aryl group" in R ^a1 or R ^b1 include a phenyl group, a naphthyl group, and the like. As the substituent on the "C6-10 aryl", preferred are halogen groups such as fluoro, chloro, bromo, and iodo; methyl, ethyl, n-propyl, isopropyl, n-butyl, C1~6 alkyl groups such as second butyl, isobutyl, tertiary butyl, n-pentyl, n-hexyl; chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, C1～6 haloalkyl groups such as 1-fluoro n-butyl; hydroxy; methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, second butoxy, isobutoxy, first C1-6 alkoxy such as tributoxy; C1-6 haloalkoxy such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, trifluoromethoxy; or cyano.

In the " ^{group represented by R c1} CO-NH-" in X ^{2 , R c1} represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group . The "C1-6 alkyl group" in R ^c1 may be a straight chain or a branched chain. Examples of the "C1-6 alkyl group" in R ^c1 include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, isopropyl, isobutyl, sec-butyl, Tertiary butyl, isopentyl, neopentyl, 2-methylbutyl, 2,2-dimethylpropyl, isohexyl, etc. As the substituent on the "C1-6 alkyl", preferred are halogen groups such as fluoro, chloro, bromo, and iodo; hydroxyl; methoxy, ethoxy, n-propoxy, isopropoxy Group, n-butoxy, second butoxy, isobutoxy, tertiary butoxy and other C1-6 alkoxy; 2-chloro-n-propoxy, 2,3-dichlorobutoxy, tri C1-6 haloalkoxy such as fluoromethoxy; C6-10 aryl groups such as phenyl and naphthyl; or cyano.

Examples of the "C6-10 aryl group" in R ^{c1 include a phenyl group and a naphthyl group.} As the substituent on the "C6-10 aryl", preferred are halogen groups such as fluoro, chloro, bromo, and iodo; methyl, ethyl, n-propyl, isopropyl, n-butyl, C1~6 alkyl groups such as second butyl, isobutyl, tertiary butyl, n-pentyl, n-hexyl; chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, C1～6 haloalkyl groups such as 1-fluoro n-butyl; hydroxy; methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, second butoxy, isobutoxy, first C1-6 alkoxy such as tributoxy; C1-6 haloalkoxy such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, trifluoromethoxy; or cyano.

Specific examples of the other group in the ² X, X ¹ include in the illustrated group of the same group.

In the present invention, X ^{2 is} preferably a halogen-substituted or unsubstituted C1-6 alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6 ~10 aryl groups.

Examples of the "halo-substituted C1-6 alkyl group" in X ^{2 include difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 2,2,2,1,1} -Pentafluoroethyl, etc. Examples of the "halo-substituted C1-6 alkoxy group" in X ^{2 include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-tris} Fluoroethoxy, 2,2,1,1-tetrafluoroethoxy, 2,2,2,1,1-pentafluoroethoxy, etc. Specific examples of the "substituted C6-10 aryl group" in X ² include: 4-chlorophenyl and other halogen substituted phenyl groups; 4-trifluoromethylphenyl and other C1-6 halogenated alkyl substituted benzenes Group; 4-trifluoromethoxyphenyl and other C1-6 haloalkoxy substituted phenyl groups and the like.

[X ³ , n] X ³ represents a halogen 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, substituted or unsubstituted C1-6 alkylsulfinyl, substituted or unsubstituted C1-6 alkylsulfinyl, pentafluorohydrosulfuryl, nitro or cyano, n represents ^{the number of X 3} and is any integer of 0-4, preferably 0-2, more preferably 0 or 1. As ^{specific examples of these groups in X 3} , the same groups as those exemplified in X ¹ can be cited. When n is 2 or more, X ³ may be the same or different from each other.

In the present invention, X ^{3 is} preferably a halogen-substituted or unsubstituted C1-6 alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6 ~10 aryl groups.

Examples of the "halo-substituted C1-6 alkyl group" in X ^{3 include difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 2,2,2,1,1} -Pentafluoroethyl, etc. Examples of the "halo-substituted C1-6 alkoxy group" in X ^{3 include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-tri} Fluoroethoxy, 2,2,1,1-tetrafluoroethoxy, 2,2,2,1,1-pentafluoroethoxy, etc. Specific examples of the "substituted C6-10 aryl group" in X ² include: 4-chlorophenyl and other halogen substituted phenyl groups; 4-trifluoromethylphenyl and other C1-6 halogenated alkyl substituted benzenes Group; 4-trifluoromethoxyphenyl and other C1-6 haloalkoxy substituted phenyl groups and the like.

The pyridinium salt of the present invention is not particularly limited by its production method. For example, the pyridinium salt of the present invention (hereinafter, sometimes referred to as "the compound of the present invention") can be obtained using the known reactions described in Examples and the like.

The compound of the present invention can also be produced by the following method, for example. [Production of N-aminopyridinium salt]

[化7]

The N-aminopyridinium salt (3) can be prepared by reacting the pyridine compound (1) with O-(mesitylsulfonyl)hydroxyamine (2). In addition to O-(mesitylsulfonyl) hydroxylamine, hydroxylamine-O-sulfonic acid, O-(diphenylphosphinyl) hydroxylamine, etc. may also be used.

[化8]

The N-aminopyridinium salt (3) can be directly used in the next condensation with the carboxylic acid compound (5), but when the stability of the matrix needs to be considered, it can be prepared as an iodide salt by salt exchange The N-aminopyridinium salt (4) is used. ^{In addition, X 1} and m in the reaction formula have the same meanings as those in the above-mentioned formula (I) and formula (II). [Condensation reaction]

[化9]

The N-aminopyridinium salt (3) or N-aminopyridinium salt (4) and the carboxylic acid compound (5) are condensed in the presence of a condensing agent used in the synthesis of amides, whereby the present invention can be produced Compound (6). As the condensing agent, dicyclohexylcarbodiimide (DCC), diisopropylcarbodiimide (DIC), 1-ethyl-3-(3-dimethylamino) Propyl)-carbodiimide (1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide, EDI) and so on. In addition, Ar in the reaction formula represents the Y moiety to which the benzene ring ^{having X 2} and (X ³ )n is bonded in the formulas (I) and (II). The substituents on the benzene ring can be appropriately changed after the condensation reaction. In addition, in the case of producing a compound in which A in the formula (I) and the formula (II) is sulfur, the dithiocarboxylic acid ester (7) may be used instead of the carboxylic acid compound (5).

[化10]

In the condensation reaction with the dithiocarboxylate (7), it is preferable to use a base such as potassium carbonate and sodium ethoxide. In addition, R in the reaction formula represents a C1-6 alkyl group such as a methyl group and an ethyl group.

The compound of the present invention has excellent effects in preventing and controlling various agricultural pests and mites and other harmful organisms that affect plant growth. In addition, the compound of the present invention has little phytotoxicity to crops and low toxicity to fish or warm-blooded animals, so it is a highly safe substance. Therefore, it is useful as an effective ingredient of an insecticide or acaricide. Furthermore, in recent years, among a large number of pests such as diamondback moths, rice planthoppers, leafhoppers, aphids, etc., resistance to various existing drugs has developed, which has caused the problem of insufficient efficacy of these drugs. It is expected that pests of resistant strains will also Effective medicine. The compound of the present invention not only shows excellent control effects on pests of susceptible strains, but also shows excellent control effects on pests of various resistant strains and mites of acaricide-resistant strains.

The compound of the present invention has excellent effects on controlling external parasites and internal parasites that harm humans and animals. In addition, it has low toxicity to fish and warm-blooded animals, so it is a highly safe substance. Therefore, it is useful as an active ingredient of a control agent for external parasites and internal parasites.

In addition, the compound of the present invention shows efficacy in the entire growth stage of the organism to be controlled, and for example, shows an excellent control effect against eggs, nymphs, larvae, pupae, and adults of mites, insects, and the like.

[Pest control agents, insecticides or acaricides] The pest control agent or insecticide or acaricide of the present invention contains at least one selected from the compounds of the present invention as an active ingredient. Regarding the pest control agent of the present invention, or the amount of the compound of the present invention contained in the insecticide or acaricide, as long as it exhibits a control effect on pests, agricultural pests or mites, there is no particular limitation. 100 parts by mass of the control agent, or insecticide or acaricide of the present invention is usually preferably in the range of 0.01 parts by mass to 90 parts by mass, more preferably in the range of 0.1 parts by mass to 50 parts by mass.

The pest control agent or insecticide or acaricide of the present invention is preferably used for cereals; vegetables; root vegetables; potatoes; flowers; fruit trees; trees such as houseplants, tea, coffee, cocoa, etc. ; Forage grass; turf; cotton and other plants. When applied to plants, the pest control agent or insecticide or acaricide of the present invention can be used for leaves, stems, stalks, flowers, buds, fruits, seeds, buds, roots, tubers, tubers, branches, cuttings, etc. Any part. In addition, the pest control agent, or insecticide or acaricide of the present invention is not particularly limited by the species of the plant to be applied. Examples of plant species include original species, varieties, improved varieties, cultivars, mutants, hybrids, and genetically modified organisms (GMO).

In order to control various agricultural pests and mites, the pest control agent of the present invention can be used for seed treatment, stem and leaf spreading, soil application, water surface application and the like.

Specific examples of various agricultural pests and mites that can be controlled by the pest control agent of the present invention are shown below.

(1) Lepidoptera (Lepidoptera) butterflies or moths (A) Moths of the family Arctiidae, such as Hyphantria cunea and Lemyra imparilis; (B) Moths of the Bucculatricidae family, such as Bucculatrix pyrivorella; (C) Moths of the family Carposinidae, such as Carposina sasakii (Carposina sasakii); (D) Moths of the family Crambidae, such as Diaphania indica (Diaphania indica) of the genus Diaphania (Diaphania spp.), and Diaphania nitidalis (Diaphania nitidalis); for example, Ostrinia spp. ) Of the Asian corn borer (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), hemp bean stalk field borer (Ostrinia scapulalis); and Chilo suppressalis, rice leaf roller (Cnaphalocrocis medinalis), peach borer (Conogethes punctiferalis), Southwest Corn Borer (Diatraea grandiosella), Glyphodes pyloalis (Glyphodes pyloalis), Cabbage Heart Borer (Hellula undalis), and Bluegrass Parapediasia teterrella (Parapediasia teterrella); (E) Moths of the family Gelechiidae, such as Helcystogramma triannulella, Pectinophora gossypiella, Phthorimaea operculella, Sitotroga cerealella; (F) Moths of the Geometridae family, such as Ascotis selenaria; (G) Moths of the family Gracilariidae, such as Caloptilia theivora, Phyllocnistis citrella, Phyllonorycter ringoniella; (H) Butterflies of the family Hesperiidae, such as Parnara guttata; (I) Moths of the family Lasiocampidae, such as Malacosoma neustria; (J) Lymantriidae (Lymantriidae) moths, such as Lymantria dispar (Lymantria spp.), Lymantria monacha (Lymantria monacha); other tea poisonous moths (Euproctis pseudoconspersa), Orgyia thyellina ；

(K) Moths of the Lyonetiidae family, such as Lyonetia clerkella (Lyonetia clerkella) and Lyonetia prunifoliella malinella (Lyonetia spp.); (L) Moths of the Noctuidae family, such as Spodoptera depravata (Spodoptera depravata) of the genus Spodoptera (Spodoptera spp.), Southern Grey-winged Spodoptera (Spodoptera eridania), Spodoptera exigua ), Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura; for example, Autographa gamma of Autographa spp., Autographa nigrisigna (Autographa nigrisigna); such as Agrotis ipsilon (Agrotis ipsilon) and Agrotis segetum (Agrotis segetum) of the genus Agrotis spp.; such as cotton bolls of the genus Helicoverpa spp. Helicoverpa armigera, Helicoverpa assulta, Helicoverpa zea; such as Heliothis spp., Heliothis armigera, Heliothis virescens ; Other white spotted moths (Aedia leucomelas), silver-striped armyworms (Ctenoplusia agnata), Eudocima tyrannus, cabbage armyworms (Mamestra brassicae), armyworms (Mythimna separata), rice moths (Naranga aenescens) , Panolis japonica, Peridroma saucia, Pseudoplusia includens, Trichoplusia ni; (M) Moths of the Nolidae family, such as Earias insulana; (N) Butterflies of the family Pieridae, such as Pieris brassicae (Pieris brassicae) and Pieris rapae crucivora (Pieris spp.); (O) Moths of the Plutella family (Plutellidae), such as Acrolepiopsis sapporensis (Acrolepiopsis sapporensis) of the genus Acrolepiopsis (Acrolepiopsis spp.), Acrolepiopsis suzukiella (Acrolepiopsis suzukiella); and Plutella xylostella; (P) Moths of the family Pyralidae, such as Cadra cautella, Elasmopalpus lignosellus, Etiella zinckenella, Galleria mellonella; (Q) Moths of the family Sphingidae, such as Manduca quinquemaculata (Manduca quinquemaculata) and Manduca sexta (Manduca sexta) of the genus Manduca spp.;

(R) Moths of the family Stathmopodidae, such as Stathmopodidae (Stathmopoda masinissa); (S) Moths of the Tineidae family, such as Tinea translucens; (T) Moths of the family Tortricidae, such as Adoxophyes honmai (Adoxophyes honmai) and Adoxophyes orana of the genus Adoxophyes spp.; such as Archips spp. Pear yellow roll moth (Archips breviplicanus), apple leaf roll moth (Archips fuscocupreanus); other spruce leaf roll moth (Choristoneura fumiferana), apple small roll moth (Cydia pomonella), Ligustrum lucidum (Eupoecilia ambiguella), pear heartworm (Grapholitha) molesta), Homona magnanima, Leguminivora glycinivorella, Lobesia botrana, Matsumuraeses phaseoli, Pandemis heparana, and Pandemis heparana (Leguminivora glycinivorella) Sparganothis pilleriana); (U) Moths of the family Yponomeutidae, such as Argyresthia conjugella.

(2) Thysanoptera pests (A) Pests of the Phlaeothripidae family (Phlaeothripidae), such as Ponticulothrips diospyrosi (Ponticulothrips diospyrosi); (B) Thripidae pests, such as Frankliniella intonsa (Frankliniella intonsa) and Frankliniella occidentalis (Frankliniella occidentalis) of the genus Frankliniella (Frankliniella spp.); such as those of the genus Thrips spp. Thrips palmi (Thrips palmi), Thrips tabaci (Thrips tabaci); other greenhouse thrips (Heliothrips haemorrhoidalis), tea yellow thrips (Scirtothrips dorsalis).

(3) Pests of the order Hemiptera (A) Archaeorrhyncha (A) Pests of the Delphacidae family, such as Laodelphax striatella, Nilaparvata lugens, Perkinsiella saccharicida, and Sogatella furcifera.

(B) Clypeorrhyncha (A) Pests of the Cicadellidae family (Cicadellidae), such as Empoasca fabae, Empoasca nipponica, Empoasca onukii, and Itai from the genus Empoasca spp. Small green leafhopper (Empoasca sakaii); other grape leafhoppers (Arboridia apicalis), black-breasted two-chambered leafhoppers (Balclutha saltuella), two-pointed large leafhoppers (Epiacanthus stramineus), black frontal two-pointed leafhoppers (Macrosteles striifrons), black Leafhopper (Nephotettix cinctinceps).

(C) Heteroptera (A) Pests of Alydidae (Alydidae), such as Riptortus clavatus; (B) Pests of Coreidae, such as Cletus punctiger and Leptocorisa chinensis; (C) Pests of the Lygaeidae family (Lygaeidae), such as Blissus leucopterus, Cavelerius saccharivorus, Togo hemipterus; (D) Pests of the Miridae family, such as Halticus insularis, Lygus lineolaris, Psuedatomoscelis seriatus, Stenodema sibiricum, Red Stenotus rubrovittatus, Trigonotylus caelestialium;

(E) Pests of the Pentatomidae family, such as Nezara antennata (Nezara antennata), Nezara viridula (Nezara viridula) of the genus Nezara spp.; for example, Eysarcoris spp. Eysarcoris aeneus (Eysarcoris aeneus), Eysarcoris lewisi, Eysarcoris ventralis (Eysarcoris ventralis); other spot bugs (Dolycoris baccarum), Eurydema rugosum (Eurydema rugosum), green, spunctatus Halyomorpha halys (Halyomorpha halys), Piezodorus hybneri (Piezodorus hybneri), Plautia crossota (Plautia crossota), Scotinophora lurida (Scotinophora lurida); (F) Pyrrhocoridae (Pyrrhocoridae) pests, such as Dysdercus cingulatus; (G) Pests of Rhopalidae (Rhopalidae), such as Rhopalus msculatus; (H) Pests of the Scutelleridae family (Scutelleridae), such as Eurygaster integriceps; (I) Pests of the Tingidae family, such as Stephanitis nashi.

(D) Sternorrhyncha (A) Pests of the family Adelgidae, such as Adelges laricis; (B) Pests of the whitefly family (Aleyrodidae), such as Bemisia argentifolii (Bemisia argentifolii), Bemisia tabaci (Bemisia tabaci) of the genus Bemisia (Bemisia spp.); other black whiteflies (Aleurocanthus spiniferus) , Citrus whitefly (Dialeurodes citri), greenhouse whitefly (Trialeurodes vaporariorum); (C) Aphididae (Aphididae) pests, such as Aphis spp. (Aphis spp.) bean aphid (Aphis craccivora), beet aphid (Aphis fabae), grass borer (Aphis forbesi), cotton aphid (Aphis gossypii), Apple aphid (Aphis pomi), elder aphid (Aphis sambuci), leaf roller aphid (Aphis spiraecola); for example, the corn aphid (Rhopalosiphum maidis) of the genus Rhopalosiphum spp., and the corn aphid (Rhopalosiphum padi) ); For example, Dysaphis plantaginea (Dysaphis plantaginea) and Dysaphis radicola (Dysaphis radicola) of the genus Dysaphis spp.; For example Macrosiphum avenae (Macrosiphum avenae) of the genus Macrosiphum spp. ), Macrosiphum euphorbiae (Macrosiphum euphorbiae); such as Myzus cerasi (Myzus cerasi), Myzus persicae (Myzus persicae), Myzus varians (Myzus varians) of Myzus spp.; other long-tube pea aphids (Acyrthosiphon pisum), Aulacorthum solani, Plum short-tailed aphid (Brachycaudus helichrysi), Cabbage aphid (Brevicoryne brassicae), Strawberry capillary aphid (Chaetosiphon fragaefolii), Myzus persicae (Hyalopterus pruni), Hyperomyzus lactucae, Lipaphis erysimi, Megoura viciae, Metopolophium dirhodum, Lettuce aphid (Nasonovia ribis-nigri), Hubu Phorodon humuli, Schizaphis graminum, Sitobion avenae, Toxoptera aurantii;

(D) Coccidae (Coccidae) pests, such as Ceroplastes ceriferus (Ceroplastes ceriferus) and Ceroplastes rubens (Ceroplastes rubens) of the genus Ceroplastes spp.; (E) Pests of the family Diaspididae, Pseudaulacaspis pentagona (Pseudaulacaspis pentagona) and Pseudaulacaspis prunicola (Pseudaulacaspis prunicola) of the genus Pseudaulacaspis (Pseudaulacaspis spp.); such as those of the genus Unaspis spp. Unaspis euonymi, Unaspis yanonensis; other Aonidiella aurantii, Comstockaspis perniciosa, Fiorinia theae, Peony. Shield scale (Pseudaonidia paeoniae); (F) Pests of Margarodidae (Margarodidae), such as Paramecium (Drosicha corpulenta) and Icerya purchasi (Icerya purchasi); (G) Pests of Phylloxeridae (Phylloxeridae), such as grape phylloxera (Viteus vitifolii); (H) Pseudococcidae (Pseudococcidae) pests, such as Planococcus spp. (Planococcus spp.) Citrus mealybugs (Planococcus citri), Japanese mealybugs (Planococcus kuraunhiae); other Lycoris solani (Phenacoccus solani) ), Pseudococcus comstocki (Pseudococcus comstocki); (I) Psyllidae (Psyllidae) pests, such as Psylla mali (Psylla mali), Psylla pyrisuga (Psylla pyrisuga) of the genus Psylla (Psylla spp.); Other citrus psyllids (Diaphorina citri).

(4) Pests of Polyphaga (A) Pests of the family Anobiidae, such as Lasioderma serricorne (Lasioderma serricorne); (B) Pests of Attelabidae, such as Byctiscus betulae and Rhynchites heros; (C) Pests of Bostrichidae (Bostrichidae), such as Lyctus brunneus (Lyctus brunneus); (D) Brentidae pests, such as Cylas formicarius; (E) Pests of Buprestidae (Buprestidae), such as Agrilus sinuatus; (F) Pests of Cerambycidae, such as Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, Xylotrechus pyrrhoderus; (G) Pests of the Chrysomelidae family (Chrysomelidae), such as Bruchus pisorum (Bruchus spp.), Bruchus rufimanus (Bruchus rufimanus); such as the northern corn rootworm (Diabrotica spp.) Diabrotica barberi), cucumber beetle (Diabrotica undecimpunctata), corn root firefly beetle (Diabrotica virgifera); for example, Phyllotreta nemorum (Phyllotreta nemorum) of Phyllotreta spp., Phyllotreta striolata ); other yellow melon (Aulacophora femoralis), green bean weevil (Callosobruchus chinensis), beet beetle beetle (Cassida nebulosa), beet beetle (Chaetocnema concinna), potato leaf beetle (Leptinotarsa decemlineata), rice minus mudworm (Oulema oryzae) ), Psylliodes angusticollis (Psylliodes angusticollis);

(H) Coccinellidae pests, such as Epilachna varivestis (Epilachna varivestis) and Epilachna vigintioctopunctata (Epilachna vigintioctopunctata) of the genus Epilachna (Epilachna spp.); (I) Curculionidae (Curculionidae) pests, such as the Mexican cotton boll weevil (Anthonomus grandis) of the genus Anthonomus spp., Anthonomus pomorum (Anthonomus pomorum); such as the valley of the weevil genus (Sitophilus spp.) Elephant (Sitophilus granarius), Corn Elephant (Sitophilus zeamais); Other Rice Weevil (Echinocnemus squameus), West Indian Sweet Potato Weevil (Euscepes postfasciatus), Pine Bark Elephant (Hylobius abietis), Alfalfa Leaf Weevil (Hypera postica), Rice Water Weevil (Lissohoptrus oryzophilus), grape black weevil (Otiorhynchus sulcatus), pea nodule elephant (Sitona lineatus), pointed cryptobeak elephant (Sphenophorus venatus); (J) Pests of the Elateridae family, such as Melanotus fortnumi (Melanotus fortnumi) and Melanotus tamsuyensis of Melanotus spp.; (K) Pests of the Nitidulidae family (Nitidulidae), such as Epuraea domina; (L) Pests of Scarabaeidae, such as Anomala cuprea (Anomala spp.), Anomala rufocuprea (Anomala rufocuprea); other Cetonia aurata, Little green beetle (Gametis jucunda), small chestnut beetle (Heptophylla picea), big chestnut beetle (Melolontha melolontha), Japanese beetle (Popillia japonica); (M) Scolytidae (Scolytidae) pests, such as Spruce typographus (Ips typographus); (N) Staphylinidae (Staphylinidae) pests, such as Paederus fuscipes; (O) Pests of the Tenebrionidae family (Tenebrionidae), such as Tenebrio molitor (Tenebrio molitor) and Tribolium castaneum (Tribolium castaneum); (P) Pests of the family Trogositidae, such as Tenebroides mauritanicus.

(5) Pests of Diptera (A) Brachycera (A) Pests of the family Agromyzidae, such as Liriomyza spp. (Liriomyza bryoniae), Liriomyza chinensis (Liriomyza chinensis), Liriomyza sativae (Liriomyza sativae), Liriomyza trifolii (Liriomyza trifolii); other pea Chromatomyia horticola (Chromatomyia horticola), Agromyza oryzae (Agromyza oryzae); (B) Pests of the Anthomyiidae family, such as Delia platura (Delia platura) and Delia radicum of the genus Delia spp.; other Pegomya cunicularia; (C) Drosophila (Drosophilidae) pests, Drosophila melanogaster (Drosophila melanogaster), spot-winged fruit fly (Drosophila suzukii) of Drosophila spp.; (D) Pests of the family Ephydridae, such as Hydrellia griseola; (E) Psilidae (Psilidae) pests, such as Psila rosae; (F) Pests of the Tephritidae family, such as Bactrocera cucurbitae (Bactrocera cucurbitae) and Bactrocera dorsalis (Bactrocera dorsalis) of the genus Bactrocera (Bactrocera spp.); such as Rhagoletis spp. Cherry fruit fly (Rhagoletis cerasi), apple fruit fly (Rhagoletis pomonella); other Mediterranean fruit fly (Ceratitis capitata), olive fruit fly (Dacus oleae).

(B) Nematocera (A) Cecidomyiidae (Cecidomyiidae) pests, such as soybean gall midge (Asphondylia yushimai), sorghum gall midge (Contarinia sorghicola), hessian gall midge (Mayetiola destructor), wheat red midge (Sitodiplosis mosellana).

(6) Pests of Orthoptera (A) Acrididae (Acrididae) pests, such as Schistocerca americana (Schistocerca americana) and desert locust (Schistocerca gregaria) of the genus Schistocerca (Schistocerca spp.); other Australian plague locusts (Chortoicetes terminifera), Moroccan locust (Dociostaurus maroccanus), Locusta migratoria, Brown migratory locust (Locustana pardalina), Red-winged locust (Nomadacris septemfasciata), Oxya yezoensis; (B) Gryllidae (Gryllidae) pests, such as house cricket (Acheta domestica), yellow-faced oil gourd (Teleogryllus emma); (C) Pests of Gryllotalpidae (Gryllotalpidae), such as Gryllotalpa orientalis; (D) Pests of Tettigoniidae, such as Tachycines asynamorus.

(7) Acari (A) Acaridida of the order Astigmata (A) Acaridae (Acaridae), such as Rhizoglyphus spp. (Rhizoglyphus echinopus), Robin (Rhizoglyphus robini); for example, Tyrophagus spp. Tyrophagus neiswanderi (Tyrophagus neiswanderi), Tyrophagus perniciosus (Tyrophagus perniciosus), Tyrophagus putrescentiae (Tyrophagus putrescentiae), Tyrophagus similis (Tyrophagus similis); and Acarus siro, Acarus ellipsoidea (Aleuroglyphus ovatus), Mycetoglyphus fungivorus;

(B) Actinedida of Prostigmata (A) Tetranychidae mites, such as Bryobia praetiosa (Bryobia praetiosa) and Bryobia rubrioculus (Bryobia rubrioculus) of Bryobia spp.; for example, the six species of Eotetranychus spp. Eotetranychus asiaticus, Eotetranychus boreus, Eotetranychus celtis, Eotetranychus geniculatus, Eotetranychus kankitus, and Eotetranychus kankitus (Eotetranychus pruni), Eotetranychus shii, Eotetranychus smithi, Eotetranychus suginamensis, Eotetranychus uncatus; for example, Oligonychus spp.) of Cryptomeria (Oligonychus hondoensis), Holly (Oligonychus ilicis), Larch (Oligonychus karamatus), Mango (Oligonychus mangiferus), Sugarcane (Oligonychus orthius), Oligonychus perseae, Oligonychus pustulosus, Oligonychus shinkajii, Oligonychus ununguis; for example, Panonychus spp. Panonychus citri (Panonychus citri), Panonychus mori, Panonychus ulmi (Panonychus ulmi); for example, Tetranychus cinnabarinus (Tetranychus spp.), Tetranychus cinnabarinus, Tetranychus spp. Tetranychus evansi, Tetranychus kanzawai, Tetranychus ludeni, Tetranychus quercivorus, Tetranychus phaselus, Tetranychus urticae, Mountain Tetranychus viennensis; for example, Aponychus corpuzae and Aponychus firmianae of the genus Aponychus spp.; for example, the green spider mites of the genus Sasanychus spp. Sasanychus akitanus, Sasanychus pusillus; for example, Shizotetranychus celarius of Shizotetranychus spp., Shizotetranychus longus, and Shizotetranychus miscanthi ), Shizotetranychus recki, Shizotetranychus schizopus; and wood sorrel such as Tetranychina harti, Tuckerella pavoniformis, Yezonychus sapporensis );

(B) Mites of the family Tenuipalpidae, such as Brevipalpus lewisi of Brevipalpus spp., Brevipalpus obovatus, Brevipalpus phoenicis ), Brevipalpus russulus, Brevipalpus californicus; For example, Tenuipalpus pacificus of Tenuipalpus spp., Tenuipalpus zhizhilashviliae; and Pineapple spider mite (Dolichotetranychus floridanus); (C) Mites of the family Eriophyidae, such as Aceria diospyri (Aceria diospyri) of the genus Aceria spp., Aceria ficus (Aceria ficus), Aceria japonica (Aceria japonica), Aceria kuko (Aceria kuko), Aceria paradianthi (Aceria paradianthi), Aceria tiyingi (Aceria tiyingi), Aceria tulipae (Aceria tulipae), Aceria zoysiea (Aceria zoysiea); for example Eriophyes chibaensis, Eriophyes emarginatae (Eriophyes emarginatae) of the genus Eriophyes (Eriophyes spp.); for example, Aculops lycopersici, Dermatophagoides (Aculops lycopersici) of the genus Aculops spp. Aculops pelekassi; for example, Aculus fockeui (Aculus fockeui) of the genus Aculus spp., Aculus schlechtendali (Aculus schlechtendali); and Acaphylla theavagrans, tea gall Mite (Calacarus carinatus), grape gall mite (Colomerus vitis), grape leaf rust mite (Calepitrimerus vitis), pear gall mite (Epitrimerus pyri), chrysanthemum leaf rust mite (Paraphytoptus kikus), Podocarpus paragonus podocarpi (Paracalacarus podocarpi) ), citrus rust mite (Phyllocotruta citri); (D) The mites of the family Transonemidae, such as Tarsonemus bilobatus (Tarsonemus bilobatus), Tarsonemus waitei (Tarsonemus waitei) of Tarsonemus spp.; and Phytonemus waitei (Phytonemus waitei). pallidus), Polyphagotarsonemus latus; (E) Mite of the family Penthaleidae, such as Penthaleus erythrocephalus (Penthaleus erythrocephalus) and Penthaleus major (Penthaleus spp.).

The pest control agent of the present invention can be combined with other effective ingredients such as fungicides, insecticides/acaricides, nematicides, and soil insecticides; plant regulators, synergists, fertilizers, soil conditioners, animal feeds, etc. Mixed or combined use. The combination of the compound of the present invention and other active ingredients can expect synergistic effects related to insecticidal/acaricidal/nematicidal activities. The synergistic effect can be calculated according to the prescribed method and by the Colby formula (Colby.SR; Calculating Synergistic and Antagonistic Responses of Herbicide Combinations; Weeds 15, 20-22, 1967) confirm.

Specific examples of insecticides/acaricides, nematicides, soil insecticides, insect repellents, etc., which can be mixed or used in combination with the pest control agent of the present invention are shown below.

(1) Acetylcholinesterase inhibitor: (A) Carbamate series: alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butantocarboxim (Butoxycarboxim), carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furosemide Furathiocarb, isoprocarb, methocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb ), thiofanox, triazamate, trimethacarb, Xylene Monochloride (XMC), xylylcarb, fenothiocarb, fenothiocarb MIPC, MPMC, MTMC, aldoxycarb, allyxycarb, aminocarb, bufencarb, bufencarb Cloethocarb (cloethocarb), metam-sodium (metam-sodium), promecarb (promecarb);

(B) Organic phosphorus series: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos , Chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, Demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, ethyl Disulfoton, ethyl-p-nitrophenyl (EPN), ethion, ethoprophos, famphur, fenamiphos, fenamiphos Phosphorus (fenitrothion), fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isocarbophos, isocarbophos Isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, two Naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate (Phorate), phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, Propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, s ulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, Trichlorfon, vamidothion, bromophos-ethyl, BRP, carbophenothion, cyanofenphos, methyl phosphate Demeton-S-methyl sulfone, dialifos, dichlofenthion, dioxabenzofos, etrimfos, fensulfothion, pyrifluthion Phosphorus (flupyrazofos), fonofos, formothion, fosmethilan, isazofos, jodfenphos, methacrifos, ethylpyrimidine Phosphorus (pirimiphos-ethyl), phosphocarb, propaphos, prothoate, sulprofos.

(2) Gamma Aminobutyric Acid (GABA)-operable chloride channel antagonist: acetoprole, chlordane, endosulfan, ethiprole ), fipronil, pyrafluprole, pyriprole, camphechlor, heptachlor, dienochlor. (3) Sodium channel modulators: Acrinathrin, d-cis-trans allethrin (d-cis-trans allethrin), d-trans allethrin (d-trans allethrin), Bifenthrin, bioallethrin, bioallethrin S-cyclopentyl isomer, bioresmethrin, cycloprothrin ), cyfluthrin, β-cyfluthrin, cyhalothrin, λ-cyhalothrin, γ-cyhalothrin, cypermethrin ), α-cypermethrin (α-cypermethrin), β-cypermethrin (β-cypermethrin), θ-cypermethrin (θ-cypermethrin), ζ-cypermethrin (ζ-cypermethrin), cypermethrin [(1R)-trans iso Structure] (cyphenothrin[(1R)-trans isomer]), deltamethrin (deltamethrin), allethrin [(EZ)-(1R)-isomer] (Empenthrin[(EZ)-(1R) -Isomer]), permethrin (esfenvalerate), etofenprox, fenpropathrin, fenvalerate, flucythrinate, flucythrin Esters (flumethrin), τ-fluvalinate (τ-fluvalinate), halfenprox, imiprothrin, kadethrin, permethrin, phenyl ether Pyrethrin [(1R)-trans isomer] (phenothrin[(1R)-trans isomer]), prallethrin, pyrethrum, resmethrin, fluorosilicone Pyrethrin (silafluofen), tefluthrin (tefluthrin), tetramethrin [(1R)-isomer] (tetramethrin[(1R)-isomer]), tetrabromothrin (tralomethrin), tetrafluthrin (Transfluthrin), allethrin (allethrin), pyrethrin (pyr ethrins), pyrethrin I, pyrethrin II, profluthrin, dimefluthrin, bioethanomethrin, Biopermethrin (biopermethrin), transpermethrin (transpermethrin), fenfluthrin (fenfluthrin), fenpirithrin (fenpirithrin), deltafluthrin (flubrocythrinate), flufenprox (flufenprox), a Metofluthrin, protrifenbute, pyresmethrin, terallethrin.

(4) Nicotinic acetylcholine receptor agonists: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, Nithiazine, thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyradifurone, flupiruimide (Flupyrimine). (5) Ectopic modulators of nicotinic acetylcholine receptors: spinetoram, spinosad. (6) Chloride channel activators: abamectin, emamectin-benzoate, lepimectin, milbemectin, Ivermectin, selamectin, doramectin, eprinomectin, moxidectin, milbemycin, mebemycin Milbemycin oxime, nemadectin. (7) Juvenile hormone analogues: hydroprene, kinoprene, methoprene, fenoxycarb, pyriproxyfen, fenfenpropan (Diofenolan), epofenonane, triprene. (8) Other non-specific inhibitors: methyl bromide, chloropicrin, sulfuryl fluoride, borax, and tartar emetic. (9) Homoptera selective feeding inhibitors: flonicamid (flonicamid), pymetrozine (pymetrozine), new quinazoline (pyrifluquinazon).

(10) Mite fertility inhibitors: clofentezine, diflovidazin, hexythiazox, etoxazole. (11) Insect midgut lining disrupter derived from microorganisms: Bacillus thuringiensis subsp. Israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai ), Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, Bt crop protein, Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab , Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/Cry35Ab1. (12) Mitochondrial ATP biosynthetic enzyme inhibitors: diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetraclosan Mite (tetradifon). (13) Oxidative phosphorylation uncoupling agents: chlorfenapyr, sulfluramid, dinitrocresol (DNOC), binapacryl, dinobuton, dinobuton dinocap). (14) Nicotinic acetylcholine receptor channel blockers: bensultap, cartap hydrochloride, nereistoxin, thiosultap-sodium , Insecticidal ring (thiocyclam). (15) Chitin synthesis inhibitors: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, flufenoxuron ( hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, buprofezin, imidacloprid ( fluazuron). (16) Diptera moulting disruptor: cyromazine. (17) Ecdysone receptor agonists: chromafenozide, halofenozide, methoxyfenozide, tebufenozide. (18) Octopamine receptor agonists: amitraz, demiditraz, chlordimeform. (19) Mitochondrial electron transport system complex III inhibitors: acequinocyl, fluacrypyrim, hydramethylnon, bifenazate. (20) Mitochondrial electron transport system complex I inhibitors: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, pyrimidine Tolfenpyrad, rotenone.

(21) Potential-dependent sodium channel blockers: indoxacarb, metaflumizone. (22) Acetyl CoA carboxylase inhibitors: spirodiclofen, spiromesifen, spirotetramat, 3-(4-chloro-2,6-dimethyl (Phenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylethyl carbonate (spiropidion). (23) Mitochondrial electron transport system complex IV inhibitors: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide. (24) Mitochondrial electron transport system complex II inhibitors: cyenopyrafen, cyflumetofen, pyflubumide. (25) Ryanodine receptor modulators: chlorantraniliprole, cyantraniliprole, flubendiamide, cyclaniliprole, fluorine Methiramid (tetraniliprole). (26) Mixed function oxidase inhibitor compound: piperonyl butoxide. (27) Arachnotoxin receptor agents: depsipeptide, cyclodepsipeptide, 24 membered cyclodepsipeptide, emodepside. (28) Other agents (the mechanism of action is unknown): 3-endo-[2-propoxy-4-(trifluoromethyl)phenoxy]-9-[5-(trifluoromethyl)-2-pyridine Oxygen]-9-azabicyclo[3.3.1]nonane (acynonapyr), azadirachtin, benzoximate, bromopropylate, quinomethionate, cryolite (Cryolite), dicofol, pyridalyl, benclothiaz, sulfur, amidoflumet, 1,3-dichloropropene , Dichloroisopropyl ether (DCIP), phenisobromolate, benzomate, metaldehyde, chlorobenzilate, clothiazoben, ringworm Dicyclanil, fenoxacrim, fentrifanil, flubenzimine, fluphenazine, gossyplure, scarab sex Japonilure, metoxadiazone, oil, sodium oleate, tetrasul, triarathene, afidopyropen, flumatoquinone ( flometoquin, flufiprole, fluensulfone, meperfluthrin, tetramethylfluthrin, tralopyril, methyl neodecyl Methylneodecanamide, fluralaner, afoxolaner, fluxametamide, 5-[5-(3,5-dichlorophenyl) -5-Trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile (CAS: 943137-49 -3) (5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-(1H-1,2,4-triazole-1-yl)benzonitril e (CAS: 943137-49-3)), broflanilide, triflumezopyrim, dicloromezotiaz, 2-[3-(ethylsulfonyl) -2-pyridyl]-5-[(trifluoromethyl)sulfonyl]benzoxazole (oxazosulfyl), other meta-diamides, N-[3-chloro-1-(3-pyridyl) )Pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]propionamide (tyclopyrazoflor).

(29) Insect repellent: (A) Benzimidazole series: fenbendazole, albendazole, triclabendazole, oxibendazole, mebendazole, orfen Oxfendazole, parbendazole, flubendazole, febantel, netobimin, thiophanate, thiabendazole, Cambendazole (cambendazole); (B) Salicylaniline series: closantel, oxyclozanide, rafoxanide, niclosamide; (C) Substituted phenols: nitroxinil, nitroscanate; (D) Pyrimidine series: pyrantel, morantel; (E) Imidazothiazole series: levamisole, tetramisole; (F) Tetrahydropyrimidine series: praziquantel, epsiprantel; (G) Other anthelmintics: cyclodiene, ryania, clorsulon, metronidazole, demiditraz, piperazine ), diethylcarbamazine, dichlorophen, monepantel, tribendimidine, amidantel, thiacetarsamide, melar Melarsomine, arsenamide.

Specific examples of fungicides that can be mixed or used in combination with the pest control agent of the present invention are shown below. (1) Inhibitors of nucleic acid biosynthesis: (A) RNA polymerase I inhibitors: benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M ; Oxadixyl, clozylacon, ofurace; (B) Adenosine deaminase inhibitors: bupirimate, dimethirimol, ethirimol; (C) DNA/RNA synthesis inhibitors: hymexazol, octhilinone; (D) DNA topoisomerase II inhibitor: oxolinic acid.

(2) Mitosis inhibitors and cell division inhibitors: (A) β-tubulin polymerization inhibitors: benomyl, carbendazim, chlorfenazole, fuberidazole, thiabendazole, thiophanate (Thiophanate), thiophanate-methyl, diethofencarb, zoxamide, ethaboxam; (B) Cell division inhibitor: pencycuron; (C) Delocalized inhibitor of spectrin-like proteins: fluopicolide.

(3) Respiratory inhibitors: (A) Complex I NADH oxidoreductase inhibitors: diflumetorim, tolfenpyrad; (B) Complex II succinate dehydrogenase inhibitors: benodanil, flutolanil, mepronil, isofetamid, fluopyram ( fluopyram, fenfuram, furmecyclox, carboxin, oxycarboxin, thifluzamide, benzovindiflupyr , Bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad ), sedaxane, boscalid, (Z)-N-{2-[3-chloro-5-(cyclopropylethynyl)-2-pyridyl]-2 -(Isopropoxyimino)ethyl}-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-methanamide (pyrapropoyne); (C) Complex III ubiquinone oxidase Qo inhibitor: azoxystrobin, coumoxystrobin, coumethoxystrobin, enoxastrobin, flufenoxystrobin ), picoxystrobin, pyraoxystrobin, pyraclostrobin, pyrametostrobin, triclopyricarb, kresoxim-methyl, Trifloxystrobin, dimoxystrobin, fenaminstrobin, metominostrobin, orysastrobin, famoxadone, fluoxastrobin (Fluoxastrobin), fenamidone, pyribencarb; (D) Complex III ubiquinone reductase Qi inhibitors: cyazofamid, amisulbrom; (E) Uncoupling agents for oxidative phosphorylation: binapacryl, meptyldinocap, dinocap, fluazinam, ferimzone; (F) Oxidative phosphorylation inhibitors (inhibitors of ATP synthase): fentin acetate, fentin chloride, and fentin hydroxide; (G) ATP production inhibitor: silthiofam; (H) Complex III: Qx (unknown) inhibitor of cytochrome bc1 (ubiquinone reductase): pyraclostrobin (ametoctradin).

(4) Amino acid and protein synthesis inhibitor (A) Methionine biosynthesis inhibitors: andoprim, cyprodinil, mepanipyrim, pyrimethanil; (B) Protein synthesis inhibitors: blasticidin-S, kasugamycin, kasugamycin hydrochloride, streptomycin, and oxytetracycline.

(5) Signal conduction inhibitor: (A) Signal transduction inhibitors: quinoxyfen, proquinazid; (B) MAP/histidine kinase inhibitors in osmotic signal transmission: fenpiclonil, fludioxonil, chlozolinate, iprodione, procymidone ( procymidone), vinclozolin (vinclozolin).

(6) Inhibitors of lipid and cell membrane synthesis: (A) Phospholipid biosynthesis, methyltransferase inhibitors: edifenphos, iprobenfos, pyrazophos, isoprothiolane; (B) Lipid peroxidizers: biphenyl, chloroneb, dichloran, quintozene, tecnazene, tetrachloromethyl Phosphorus (tolclofos-methyl), etridiazole (etridiazole); (C) Agents that act on cell membranes: iodocarb, propamocarb, propamocarb-hydrochloride, propamocarb -fosetylate), prothiocarb; (D) Microorganisms that disturb the cell membrane of pathogenic bacteria: Bacillus subtilis, Bacillus subtilis strain QST713, Bacillus subtilis strain FZB24, Bacillus subtilis MBI600 strain MBI600), Bacillus subtilis strain D747 (bacillus subtilis strain D747); (E) Agents that disrupt cell membranes: extracts of Melaleuca alternifolia (tea tree).

(7) Sterol biosynthesis inhibitor of cell membrane: (A) C14 demethylation inhibitors in sterol biosynthesis: triforine, pyrifenox, pyrisoxazole, fenarimol, furfur Flurprimidol, nuarimol, imazalil, imazalil-sulphate, oxpoconazole, pefurazoate, prochloraz ), triflumizole, viniconazole, azaconazole, bitertanol, bromuconazole, cyproconazole, benzyl chloride Diclobutrazol, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, niconazole (Fenbuconazole), fluquinconazole, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, Iimibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, fluquinconazole, silicofluoride Simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, voriconazole ); (B) Inhibitors of Δ14 reductase and Δ8→Δ7-isomerase in sterol biosynthesis: aldimorph, dodemorph, dodemorph acetate, butyl Fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine; (C) 3-keto-reductase inhibitors in C4 demethylation of sterol biosynthesis system: fenhexamid and fenpyrazamine; (D) Squalene epoxidase inhibitors of sterol biosynthesis system: pyributicarb, naftifine, terbinafine.

(8) Cell wall synthesis inhibitor (A) Trehalase inhibitor: validamycin; (B) Chitin synthase inhibitors: polyoxins, polyoxorim; (C) Cellulose synthase inhibitors: dimethomorph, flumorph, pyrimorph, benthiavalicarb, iprovalicarb, and Tolprocarb, valifenalate, mandipropamid.

(9) Melanin biosynthesis inhibitor (A) Reductase inhibitors of melanin biosynthesis: fthalide, pyroquilon, tricyclazole; (B) Dehydration enzyme inhibitors of melanin biosynthesis: carpropamid, diclocymet, fenoxanil.

(10) Resistance inducer of host plant: (A) Agents acting on the synthetic pathway of salicylic acid: acibenzolar-S-methyl; (B) Others: probenazole, tiadinil, isotianil, laminarin, reynoutria sachalinensis extract.

(11) Drugs with unknown effects: cymoxanil, fosetyl-aluminium, phosphoric acid (phosphate), tecloftalam, imidazosin ( triazoxide, flusulfamide, diclomezine, methasulfocarb, cyflufenamid, metrafenone, pyriofenone, docarbutin (Dodine), dodine free base (dodine free base), flutianil (flutianil).

(12) Agents with multiple points of action: copper (copper salt), bordeaux mixture, copper hydroxide, copper naphthalate, copper oxide ( copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide, ferbam, mancozeb (Mancozeb), maneb, mancopper, metiram, polycarbamate, propineb, thiram, Zineb, ziram, captan, captafol, folpet, chlorothalonil, dichlofluanid, parabens Tolylfluanid, guazatine, iminoctadine triacetate, iminoctadine trialbesilate, anilazine, dithianon, Quinomethionate, fluoroimide.

(13) Other drugs: DBEDC, fluorofolpet, guazatine acetate, bis(8-quinolinolato) copper (II)), propamidine, chloropicrin, cyprofuram, agrobacterium, bethoxazin, diphenylamine, methyl isothiocyanate Esters (MITC) (methyl isothiocyanate), midomycin (mildiomycin), capsaicin (capsaicin), thiazol (cufraneb), cyprosulfamide (cyprosulfamide), dazomet (dazomet), debacarb ), dichlorophen, difenzoquat, difenzoquat methyl sulfonate, flumetover, fosetyl-calcium, three Fosetyl-sodium, irumamycin, natamycin, nitrothal isopropyl, oxamocarb, propanosine sodium, nitrothal Pyrrolnitrin, tebufloquin, tolnifanide, zarilamide, Algophase, Amicarthiazol, fluthiazole Oxathiapiprolin, metiram zinc, benthiazole, trichlamide, uniconazole, mildomycin, oxofen Xin (Oxyfenthiin), Picarbutrazox (picarbutrazox).

Specific examples of plant regulators that can be mixed or used in combination with the pest control agent of the present invention are shown below. 1-methylcyclopropene, 2,3,5-triiodobenzoic acid, indole acetic acid (IAA), indole butyric acid (IBA), 2-methyl-4-chlorophenoxy acetic acid (MCPA), dimethyl Tetrachlorobutyric acid (MCPB), 4-CPA, 5-aminoacetyl propionate hydrochloride, 6-benzylaminopurine, abscisic acid, tetraestrone hydrochloride, pyrimidinol ( ancymidol, butralin, calcium carbonate, calcium chloride, calcium formate, calcium peroxide, lime sulfur, calcium sulfate, Chlormequat Chloride, Chlorpropham, Choline Chloride, Cloprop, cyanamide, Cyclanilide, daminozide, decanol, dichlorprop, dichlorprop, dikegulac, Dimethipin, Diquat, Ethephon, Ethychlozate, Flumetralin, Flurprimidol, Forchlorfenuron, Gibberellin Gibberellin A (gibberellin A), gibberellin A3 (gibberellin A3), hymexazol, inabenfide, isoprothiolane, kinetin, hydrazine maleate, fluoride Mefluidide, mepiquat chloride, oxidized glutathione, paclobutrazol, pendimethalin, prohexadione-calcium, jasmone ( Prohydrojasmon, Pyraflufen-ethyl, Sintofen, Sodium 1-naphthaleneacetate, Sodium cyanate, streptomycin, thidiazuron, Triapenthenol, Trifos, Trinexapac-ethyl, uniconazole P, 1-naphthylacetamide.

[External Parasite Control Agent] The ectoparasite control agent of the present invention contains at least one selected from the pyridinium salt of the present invention as an active ingredient. As long as the ectoparasite control effect is shown, the amount of the compound of the present invention contained in the ectoparasite control agent of the present invention is not particularly limited, and it is usually preferably 0.01 mass relative to 100 parts by mass of the control agent of the present invention The range of parts to 95 parts by mass.

Examples of host animals to be treated with the ectoparasite control agent of the present invention include pet animals such as dogs and cats; pet birds; domestic animals such as cattle, horses, pigs, and sheep; and warm-blooded animals such as poultry. In addition to this, there are also bees, stag beetles, and unicorns.

The ectoparasite control agent of the present invention can be administered by a known veterinary method (topical, oral, parenteral, or subcutaneous administration). Examples of this method include: oral administration to animals by mixing tablets, capsules, feed, etc.; and administration by immersion liquid, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), etc. The method of animal administration; the method of topical administration of oily or aqueous liquids by spraying, pour on, spot on, etc.; mixing the external parasite control agent in the resin, and the The kneaded material is formed into a suitable shape such as a collar and ear tag, and then it is worn on an animal to be locally administered.

External parasites are parasitic in the body and surface of host animals, especially warm-blooded animals. In detail, it is parasitic on the back, underarms, lower abdomen, internal thighs, etc. of the host animal, and the animal obtains nutrients such as blood or dander, so it can live. Examples of external parasites include mites, lice, fleas, mosquitoes, sting flies, and sarcophagus. Specific examples of ectoparasites that can be controlled by the ectoparasite control agent of the present invention are shown below.

(1) Acari Dermanyssidae mites, Macronyssidae mites, Laelapidae mites, Varroidae mites, Argasidae mites, Ixodes mites ( Ixodidae mites, Psoroptidae mites, Sarcoptidae mites, Knemidokoptidae mites, Demodexidae mites, Trombiculidae mites , Stag beetle and other insect parasitic mites. (2) Phthiraptera Haematopinidae (Haematopinidae) lice, jaw lice (Linognathidae) lice, short-horned bird lice (Menoponidae) bird lice, long-horned bird lice (Philopteridae) bird lice, beast bird lice (Trichodectidae) Bird lice. (3) Siphonaptera Fleas of Pulicidae, such as Ctenocephalides canis (Ctenocephalides spp.) and Ctenocephalides felis; Fleas of Tungidae, Ceratophyllidae, and Leptopsyllidae. (4) Hemiptera. (5) Pests of Diptera Culicidae mosquitoes, Simuliidae gnats, Ceratopogonidae midges, Tabanidae flies, Muscidae flies, Glossinidae tsetse flies, Sarcophagidae, Hippoboscidae (Hippoboscidae), Calliphoridae (Calliphoridae), Oestridae (Oestridae).

[Internal parasite control or repellent] The internal parasite control or repellent of the present invention contains at least one selected from the pyridinium salt of the present invention as an active ingredient. As long as the internal parasite control effect is shown, the amount of the compound of the present invention contained in the internal parasite control or repellent of the present invention is not particularly limited, and is usually higher than 100 parts by mass of the control or repellent of the present invention. It is preferably in the range of 0.01 parts by mass to 95 parts by mass.

The parasites that are the target of the internal parasite control or repellent of the present invention parasitize (internal parasites) in host animals, especially warm-blooded animals or fish. Examples of host animals effective for the internal parasite control or repellent of the present invention include humans, livestock mammals (for example, cows, horses, pigs, sheep, goats, etc.), experimental animals (for example, mice, rats, Gerbils, etc.), pet animals (for example, hamsters, guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, etc.), wild and zoo mammals (monkeys, foxes, deer, bison, etc.), poultry (turkeys) , Ducks, chickens, quails, geese, etc.), pet birds (pigeons, parrots, nine-guan birds, Munbirds, parrots, white-rumped Munias, canaries, etc.) and other warm-blooded animals; or salmon, trout, koi and other fish. By preventing and repelling parasites, parasitic diseases transmitted by parasites can be prevented or treated.

As the parasites to be controlled or repelled, the following can be cited. (1) Nematodes of the order Dioctophymatida (A) Dioctophymatidae (Dioctophymatidae), for example Dioctophyma renale (Dioctophyma spp.); (B) Bulkworms of the family Soboliphymatidae, such as Soboliphyme abei of Soboliphyme spp. and Soboliphyme baturini.

(2) Nematodes of the order Trichocephalida (A) Trichinella spiralis (Trichinellidae), such as Trichinella spiralis (Trichinella spp.); (B) Trichuridae whipworms, such as Capillaria annulata (Capillaria annulata), Capillaria contorta, Capillaria hepatica, Perforation Capillaria perforans, Capillaria plica (Capillaria plica), Capillaria suis (Capillaria suis); Trichuris vulpis (Trichuris vulpis), Trichuris discolor (Trichuris discolor), sheep Trichuris ovis, Trichuris skrjabini, Trichuris suis.

(3) Nematodes of the order Rhabditida Strongyloides (Strongyloididae), such as Strongyloides spp., Strongyloides papillosus, Strongyloides planiceps, Strongyloides ransomi), Strongyloides suis (Strongyloides suis), Strongyloides stercoralis (Strongyloides stercoralis), Strongyloides tumefaciens (Strongyloides tumefaciens), Strongyloides ratti (Strongyloides ratti).

(4) Nematodes of the order Strongylida Hookworms of the family Ancylostomatidae, such as Ancylostoma braziliense of Ancylostoma spp., Ancylostoma caninum, Ancylostoma duodenale, and Ancylostoma duodenale Nematode (Ancylostoma tubaeforme); Uncinaria stenocephala of Uncinaria stenocephala; Bunostomum phlebotomum and Bunostomum of Bunostomum spp. trigonocephalum).

(5) Nematodes of the order Strongylida (A) Angiostrongylidae (Angiostrongylidae) nematodes, such as Aelurostrongylus spp. (Aelurostrongylus abstrusus); Angiostrongylus spp. (Angiostrongylus spp.) Angiostrongylus vasorum, Angiostrongylus cantonesis (Angiostrongylus cantonesis); (B) Nematodes of the family Crenosomatidae, such as Crenosoma aerophila (Crenosoma aerophila) and Crenosoma vulpis (Crenosoma vulpis) of the genus Crenosoma spp.; (C) Filaroididae (Filaroididae) nematodes, such as Filaroides spp. (Filaroides hirthi) and Filaroides osleri (Filaroides osleri); (D) Metastrongylidae (Metastrongylidae), such as Metastrongylus spp. (Metastrongylus apri), asymmetric Metastrongylus asymmetricus, and round after yin Nematode (Metastrongylus pudendotectus), Metastrongylus salmi (Metastrongylus salmi); (E) Syngamidae, for example, Cyathostoma bronchialis of Cyathostoma spp.; Syngamus skrjabinomorpha of Syngamus spp. , Trachea than wing nematode (Syngamus trachea).

(6) Nematodes of the order Strongylida (A) Moline worms (Molineidae), such as Nematodirus spp. Nematodirus filicollis (Nematodirus filicollis), Nematodirus spathiger; (B) Dictyocaulidae (Dictyocaulidae) nematodes, such as Dictyocaulus spp. (Dictyocaulus spp.) Dictyocaulus filaria, Viviparous Dictyocaulus viviparus; (C) Nematodes of the Haemonchidae family, such as Haemonchus contortus of Haemonchus spp.; Dactylus contortus of Mecistocirrus spp. (Mecistocirrus digitatus); (D) Haemonchidae nematodes, such as Ostertagia ostertagi (Ostertagia spp.); (E) Nematodes resembling Heligmonellidae, such as Nippostrongylus braziliensis of Nippostrongylus spp.; (F) Nematodes of the Trichostrongylidae family, such as Trichostrongylus axei of Trichostrongylus spp., Trichostrongylus colubriformis, Trichostrongylus tenuis); Hyostrongylus rubidus (Hyostrongylus spp.); Obeliscoides cuniculi (Obeliscoides spp.).

(7) Nematodes of the order Strongylida (A) Nematodes of the Chabertiidae family, such as Chabertia ovina of the genus Chabertia spp.; Oesophagostomum of the genus Oesophagostomum spp. brevicaudatum, Oesophagostomum columbianum, Oesophagostomum dentatum, Oesophagostomum georgianum, Oesophagostomum maplephagoulatum, Oesophagostomum maplephagoulatum, Oesophagostomum maplephagoulas Oesophagostomum radiatum, Oesophagostomum venulosum, Oesophagostomum watanabei; (B) Nematodes of Stephanuridae, such as Stephanurus dentatus of Stephanurus spp.; (C) Strongylidae (Strongylidae) nematodes, such as Strongylus asini (Strongylus asini), Strongylus edentatus (Strongylus edentatus), Strongylus equinus, Common Strongylidae (Strongylus vulgaris).

(8) Nematodes of the order Oxyurida Oxyuridae nematodes, such as Enterobius spp. chimpanzee pinworms (Enterobius anthropopitheci), vermicular nematodes (Enterobius vermicularis); Oxyuris spp. Oxyuris equi; Passalurus ambiguus (Passalurus spp.).

(9) Nematodes of the order Ascaridida (A) Nematodes of the Ascaridiidae family (Ascaridiidae), such as Ascaridia galli (Ascaridia spp.); (B) Nematodes of the family Heterakidae, such as Heterakis beramporia of Heterakis spp., Heterakis brevispiculum, Heterakis gallinarum), Heterakis pusilla (Heterakis pusilla), Heterakis putaustralis (Heterakis putaustralis); (C) Nematodes of the family Anisakidae, such as Anisakis simplex of the genus Anisakis spp.; (D) Nematodes of the Ascarididae family, such as Ascaris lumbricoides and Ascaris suum of Ascaris spp.; Parascaris equine (Parascaris spp.) equorum); (E) Nematodes of the Toxocaridae family (Toxocaridae), such as Toxocara canis (Toxocara spp.), Toxocara leonina, Toxocarasuum, Toxocara vitulorum (Toxocara vitulorum), Toxocara cati (Toxocara cati).

(10) Nematodes of the order Spirurida (A) Onchocercidae (Onchocercidae) nematodes, such as Brugia spp. (Brugia malayi), Pahangi (Brugia pahangi), Pat Brugia patei; Dipetalonema reconditum (Dipetalonema reconditum) of the genus Dipetalonema spp.; Dirofilaria immitis (Dirofilaria immitis) of the genus Dirofilaria (Dirofilaria spp.); Filaria Filaria oculi (Filaria spp.); Onchocerca cervicalis (Onchocerca cervicalis), Onchocerca gibsoni (Onchocerca gibsoni), laryngoma (Onchocerca spp.) Onchocerca gutturosa (Onchocerca gutturosa); (B) Nematodes of the family Setariidae, such as Setaria digitata (Setaria digitata) of the genus Setaria (Setaria spp.), Setaria equina (Setaria equina), and Milky filamentous nematodes ( Setaria labiatopapillosa), Setaria marshalli (Setaria marshalli); Wuchereria bancrofti (Wuchereria bancrofti) of the genus Wuchereria spp.; (C) Filariidae (Filariidae) nematodes, such as Parafilaria spp. (Parafilaria multipapillosa); Crown filaria (Stephanofilaria spp.) Stephanofilaria assamensis, Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria okinawaensis, Stephanofilaria stilesi.

(11) Nematodes of the order Spirurida (A) Nematodes of the family Gnathostomatidae, such as Gnathostoma doloresi (Gnathostoma doloresi) and Gnathostoma spinigerum (Gnathostoma spp.); (B) Nematodes of the Habronematidae family, such as Habronema majus of Habronema spp., Habronema microstoma, Habronema muscae; Draschia megastoma of the genus (Draschia spp.); (C) Nematodes of the family Physalopteridae, such as Physaloptera canis (Physaloptera spp.), Physaloptera cesticillata, and Physaloptera erdocyona), Physaloptera felidis, Physaloptera gemina, Physaloptera papilloradiata, Physaloptera praeputialis, Pedopria Such as Physaloptera pseudopraerutialis, Physaloptera rara, Physaloptera sibirica, and Physaloptera vulpineus; (D) Nematodes of the family Gongylonematidae, such as Gongylonema pulchrum of the genus Gongylonema (Gongylonema spp.); (E) Nematodes of the family Spirocercidae, such as Ascarops strongylina (Ascarops strongylina) of the genus Ascarops spp.; (F) Nematodes of the family Thelaziidae, such as Thelazia callipaeda of Thelazia spp., Thelazia gulosa, Thelazia lacrymalis, Lourdes West sucking nematode (Thelazia rhodesi), Scriabin's sucking nematode (Thelazia skrjabini).

[Control agents related to other harmful organisms] In addition, the compounds of the present invention are useful for pests that have poisonous needles or venoms that can harm humans and animals, pests that transmit various pathogens/pathogenic bacteria, and pests that cause discomfort to humans (toxic pests/hygienic pests/unpleasant pests, etc.) The control effect is excellent.

The specific example is shown below. (1) Pests of Hymenoptera Bees of the Argidae family (Argidae), Cynipidae (Cynipidae) bees, Diprionidae (Diprionidae) bees, Formicidae (Formicidae) ants, Mutillidae (Mutillidae) bees, Vespidae (Vespidae) Bee.

(2) Other pests Cockroaches (Blattodea), termites (termite), spiders (Araneae), centipedes (cetipede), horse land (millipede), crustaceans (crustacea), bed bugs (Cimex lectularius). [Example]

[Preparation formula] Several formulations of pest control agents, insecticides or acaricides, external parasite control agents, or internal parasite control or repellents of the present invention are shown, but the additives and the addition ratio should not be limited to these examples , Can be changed in a wide range. The parts in the formulations represent parts by weight.

The formulations for agricultural and horticultural and rice preparations are shown below.

(Formulation 1: Hydrating agent) 40 parts of the compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate and 3 parts of alkyl naphthalene sulfonate are uniformly mixed and pulverized to fineness, thereby obtaining a hydrating agent with 40% active ingredient.

(Formulation 2: Emulsion) 30 parts of the compound of 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 with 30% active ingredient.

(Formulation 3: Granules) 5 parts of the compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are uniformly mixed and pulverized to fineness, and then granulated into granules with a diameter of 0.5 mm to 1.0 mm, thereby Obtained 5% active ingredient granules.

(Preparation 4: Granules) 5 parts of the compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctyl sulfosuccinate sodium salt and 1 part of potassium phosphate are thoroughly crushed and mixed, water is added to fully knead, and then granulated and dried , So as to obtain 5% active ingredient granules.

(Formulation 5: Suspending agent) Mix 10 parts of the compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of polycarboxylate sodium salt, 10 parts of glycerin, 0.2 part of xanthan gum and 73.8 parts of water, and perform wet grinding until the particle size When it becomes 3 microns or less, a suspension containing 10% of the active ingredient is obtained.

The formulations of external parasite control agents or internal parasite control or repellent agents are shown below.

(Formulation 6: Granules) Dissolve 5 parts of the compound of the present invention in an organic solvent to obtain a solution, spray the solution on 94 parts of kaolin and 1 part of white carbon, and then evaporate the solvent under reduced pressure. The particles can be mixed with animal bait.

(Preparation 7: Injection) 0.1 to 1 part of the compound of the present invention is uniformly mixed with 99 to 99.9 parts of peanut oil, and then filtered and sterilized by a sterilizing filter.

(Formulation 8: Pouring agent) 5 parts of the compound of the present invention, 10 parts of myristate and 85 parts of isopropanol are uniformly mixed to obtain a pouring agent.

(Preparation 9: Dispensing agent) 10 to 15 parts of the compound of the present invention, 10 parts of palmitate and 75 to 80 parts of isopropanol are uniformly mixed to obtain a spot coating agent.

(Formulation 10: Spray) 1 part of the compound of the present invention, 10 parts of propylene glycol and 89 parts of isopropanol are uniformly mixed to obtain a spray.

Next, a synthesis example is shown, and the present invention is further described in detail. Among them, the present invention is not limited in any way by the following embodiments.

[Example 1] Pyridin-1-ium-1-yl(3-(4'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)propynyl)amide Synthesis of [Pyridin-1-ium-1-yl(3-(4'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)propioloyl)amide] [Step 1] (3-(4- Synthesis of (bromophenyl) propynyl) (pyridin-1-ium-1-yl) amide [(3-(4-Bromophenyl)propioloyl)(pyridin-1-ium-1-yl)amide] 11]

3-(4-Bromophenyl)propioic acid (0.56 g) was dissolved in dichloromethane (8 ml), and 1-aminopyridinium iodide (0.66 g) and N-(3 -Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (0.47 g), 1-hydroxybenzotriazole hydrate (0.33 g), triethylamine (0.50 g) , Stir at room temperature for 4 hours. Water was added to the resultant, and the reaction product was extracted with chloroform. The organic layer was dried and filtered with anhydrous magnesium sulfate, and then the solvent was distilled off. The obtained residue was purified by silica gel chromatography to obtain 0.054 g of the title compound with a yield of 7%.

[Step 2] Pyridin-1-ium-1-yl(3-(4'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)propynyl)amide [ Synthesis of Pyridin-1-ium-1-yl(3-(4'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)propioloyl)amide] [化12]

(3-(4-Bromophenyl)propynyl)(pyridinium-1-yl)amide (0.54 g) was dissolved in a mixed solvent of water and acetonitrile (4 ml), and the resultant Add (4-(trifluoromethoxy) phenyl) boric acid (0.074 g), potassium carbonate (0.074 g), tetrakis(triphenylphosphine) palladium(0) (0.010 g), heat and reflux Stir for 3 hours. Then, the obtained liquid was cooled to room temperature. Concentrate under reduced pressure. The obtained concentrate was purified by silica gel column chromatography, thereby obtaining 0.085 g of the title compound with a yield of 90%.

[Example 2] (2,2-Difluoro-2-(4'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)acetyl)(pyridine-1-ium-1-yl )Amide [(2,2-difluoro-2-(4'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)acetyl)(pyridin-1-ium-1-yl)amide] synthesis

[Step 1] (2-(4-Bromophenyl)-2,2-difluoroacetinyl)(pyridinium-1-yl)amide [(2-(4-bromophenyl)-2, Synthesis of 2-difluoroacetyl)(pyridin-1-ium-1-yl)amide] [Chemical 13]

Dissolve 2-(4-bromophenyl)-2,2-difluoroacetic acid (0.35 g) in dichloromethane (3 ml), and add 1-aminopyridinium iodide (0.37 g) to the resultant , N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (0.27 g), 1-hydroxybenzotriazole hydrate (0.19 g) and triethyl Amine (0.28 g), stirred at room temperature for 4 hours. Water was added to the resultant, and extraction was performed with chloroform. The organic layer was dried and filtered with anhydrous magnesium sulfate, and then the solvent was distilled off. The obtained residue was purified by silica gel chromatography to obtain 0.12 g of the title compound with a yield of 26%.

[Step 2] (2,2-Difluoro-2-(4'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)acetyl)(pyridine-1-ium -1-yl)amide [(2,2-difluoro-2-(4'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)acetyl)(pyridin-1-ium-1-yl ) Synthesis of amide] [化14]

Dissolve (2-(4-bromophenyl)-2,2-difluoroacetonitrile)(pyridinium-1-yl)amide (0.06 g) in a mixed solvent of water and acetonitrile (4 ml ), add (4-(trifluoromethoxy)phenyl)boronic acid (0.057 g), potassium carbonate (0.076 g) and tetrakis(triphenylphosphine)palladium (0) (0.010 g) to the resultant, Heat and stir under reflux for 3 hours. The resultant was cooled to room temperature and concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography to obtain 0.077 g of the title compound with a yield of 98%.

[Example 3] Pyridin-1-ium-1-yl (3-(4'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)propionyl)amide [Pyridin-1-ium Synthesis of -1-yl(3-(4'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)propanoyl)amide]

[Step 1] (3-(4-Bromophenyl)propanoyl)(pyridin-1-ium-1-yl)amide [(3-(4-bromophenyl)propanoyl)(pyridin-1-ium-1 -yl)amide] Synthesis [化15]

3-(4-Bromophenyl)propionic acid (0.57 g) was dissolved in dichloromethane (8 ml), and 1-aminopyridinium iodide (0.66 g), N-(3- Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (0.47 g), 1-hydroxybenzotriazole hydrate (0.33 g) and triethylamine (0.50 g), Stir at room temperature for 4 hours. Water was added to the resultant, and extraction was performed with chloroform. The organic layer was dried and filtered with anhydrous magnesium sulfate, and the solvent was distilled off. The obtained residue was purified by silica gel chromatography to obtain 0.55 g of the title compound with a yield of 72%.

[Step 2] Pyridin-1-ium-1-yl(3-(4'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)propionyl)amide [Pyridin Synthesis of -1-ium-1-yl(3-(4'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)propanoyl)amide] [化16]

Dissolve (3-(4-bromophenyl)propionyl)(pyridinium-1-yl)amide (0.15 g) in a mixed solvent of water and acetonitrile (4 ml), and add Add (4-(tetrafluoroethoxy)phenyl)boronic acid (0.21 g), potassium carbonate (0.21 g) and tetrakis(triphenylphosphine)palladium(0) (0.028 g), heat and stir under reflux 3 hours. The resultant was cooled to room temperature and concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography, thereby obtaining 0.17 g of the title compound with a yield of 83%.

[Example 4] Pyridin-1-ium-1-yl (2-(4'-(1,1,2,2-tetrafluoroethoxy)-[1,1'-biphenyl]-4-yl)acetyl) Synthesis of Pyridin-1-ium-1-yl(2-(4'-(1,1,2,2-tetrafluoroethoxy)-[1,1'-biphenyl]-4-yl)acetyl)amide]

[Step 1] (2-(4-Bromophenyl)acetyl)(pyridin-1-yl)amide [(2-(4-Bromophenyl)acetyl)(pyridin-1-ium-1 -yl)amide] Synthesis [化17]

2-(4-Bromophenyl)acetic acid (2 g) was dissolved in toluene (4 ml), and thiol chloride (2 ml) was added to the resultant, followed by stirring at 90°C for 3 hours. The resultant was left to cool, and the solvent was distilled off. Dichloromethane (4 ml), 1-aminopyridinium iodide (2.48 g) and triethylamine (2.8 g) were added to the residue, and the mixture was stirred at room temperature for 5 hours. The resultant was concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography to obtain 1.61 g of the title compound with a yield of 59%.

[Step 2] Pyridin-1-ium-1-yl (2-(4'-(1,1,2,2-tetrafluoroethoxy)-[1,1'-biphenyl]-4-yl) Pyridin-1-ium-1-yl(2-(4'-(1,1,2,2-tetrafluoroethoxy)-[1,1'-biphenyl]-4-yl)acetyl) Synthesis of amide] [化18]

Dissolve (2-(4-bromophenyl)acetyl)(pyridinium-1-yl)amide (0.12 g) in a mixed solvent of water and acetonitrile (4 ml), and add Add (4-(1,1,2,2-tetrafluoroethoxy)phenyl)boronic acid (0.26 g), potassium carbonate (0.17 g) and tetrakis(triphenylphosphine)palladium(0) (0.023 g) , Heating and stirring under reflux for 3 hours. The resultant was cooled to room temperature and concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography, thereby obtaining 0.14 g of the title compound with a yield of 86%.

[Example 5] Pyridine-1-ium-1-yl (2-(4'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)cyclopropane-1-carbonyl) Synthesis of amide [Pyridin-1-ium-1-yl(2-(4'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)cyclopropane-1-carbonyl)amide] [Step 1] (2-(4-Bromophenyl)cyclopropane-1-carbonyl)(pyridin-1-yl)amide ((2-(4-Bromophenyl)cyclopropane-1-carbonyl)(pyridin-1- ium-1-yl)amide) [化19]

2-(4-Bromophenyl)cyclopropane-1-carboxylic acid (0.23 g) was dissolved in dichloromethane (2 ml), and 1-aminopyridinium iodide (0.25 g), N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (0.18 g), 1-hydroxybenzotriazole hydrate (0.13 g) and triethylamine (0.19 g), stirred at room temperature for 4 hours. Water was added to the resultant, and extraction was performed with chloroform. Then, the organic layer was dried with anhydrous magnesium sulfate and filtered. Then, the solvent was distilled off. The obtained residue was purified by silica gel chromatography to obtain 0.22 g of the title compound with a yield of 71%.

[Step 2] Pyridin-1-ium-1-yl(2-(4'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)cyclopropane-1-carbonyl)an Synthesis of Amine [Pyridin-1-ium-1-yl(2-(4'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)cyclopropane-1-carbonyl)amide] [化20]

Dissolve (2-(4-bromophenyl)cyclopropane-1-carbonyl)(pyridinium-1-yl)amide (0.22 g) in a mixed solvent of water and acetonitrile (4 ml), and add (4-(trifluoromethoxy)phenyl)boronic acid (0.21 g), potassium carbonate (0.27 g) and tetrakis(triphenylphosphine)palladium(0) (0.039 g) were added to the resultant, heated and Stir under reflux for 3 hours. The obtained liquid was cooled to room temperature, and then concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography, thereby obtaining 0.20 g of the title compound with a yield of 75%.

Examples of the compounds of the present invention produced by the same method as in the above-mentioned Examples are shown in Table 1. Table 1 shows the compound represented by formula (I-a) among the compounds of the present invention. In Table 1, Me represents a methyl group, Et represents an ethyl group, and Ph represents a phenyl group. When expressing Y, the bond marked with * is bonded to the carbonyl group in the pyridinium salt, and the bond marked with ** is bonded to the phenyl group. Enter the physical properties of the compound in the "Properties" column. As physical property data, properties or melting point (m.p.) are recorded.

[化21]

[Table 1]

Furthermore, examples of the compound of the present invention produced by the same method as in the above-mentioned examples are shown in Table 2. Enter the physical properties of the compound in the "Properties" column. As physical property data, properties or melting point (m.p.) are recorded.

m.p. 114-116℃ f-2

m.p. 150-152℃ [Table 2] Compound number Structural formula Physical properties f-1

mp 114-116℃ f-2

mp 150-152℃

For the compounds of compound number e-18, compound number e-19, and compound number e-22, nuclear magnetic resonance (NMR) data is shown below. e-18: ¹ H-NMR (CDCl ₃ , δppm) 1.23 (t, 3H), 2.73 (m, 2H), 3.08 (m, 1H), 4.43 (t, 2H), 6.75 (m, 1H), 6.88 (m, 1H), 6.98 (m, 1H), 7.21 (m, 1H), 7.61 (m, 2H), 7.90 (t, 1H), 8.48 (m, 2H). e-19: ¹ H-NMR ( CDCl ₃ , δppm) 1.25 (d, 3H), 2.76 (m, 2H), 3.12 (m, 1H), 7.41 (d, 2H), 7.46 (d, 2H), 7.58 (m, 2H), 7.88 (t , 1H), 8. 37 (m, 2H). e-22: ¹ H-NMR (CDCl ₃ , δppm) 1.24 (d, 3H), 2.72 (m, 1H), 3.02 (m, 1H), 6.03 ( m, 1H), 7.05 (d, 2H), 7.26 (d, 2H), 7.59 (m, 2H), 7.86 (t, 1H), 8.38 (m, 2H).

[Biological test] The following test examples show that the compound of the present invention is effectively used as an active ingredient of a pest control agent. "Parts" is the basis of weight.

(Preparation of test emulsion) 5 parts of the compound of the present invention, 93.6 parts of dimethylformamide, and 1.4 parts of polyoxyethylene alkyl aryl ether were mixed and dissolved to prepare an emulsion (I) with 5% of the active ingredient.

(1) Effectiveness test on Mythimna separata using artificial feed Mix 0.8 g of commercially available artificial feed (insect LFS (insecta LFS), manufactured by Nippon Agricultural Industry Co., Ltd.) and 1 μl of emulsion (I), and put them in a plastic test container (1.4 ml capacity) in each treatment area. Add 0.2 g as test feed. Two second-instar larvae of Mythimna separata were inoculated in each treatment area and sealed with a plastic cover. Place it in a constant temperature room at 25°C, and study the insecticidal rate and food intake on the 5th day. The test was repeated twice. In addition, the test was conducted under the same conditions except that the compound of the present invention was removed from the emulsion (I), and the test was set as the vehicle control zone.

For compounds with compound number a-1, compound number e-1, compound number e-2, compound number e-4, compound number e-5, and compound number f-1, an efficacy test against the armyworm was performed. The insecticidal rate of any compound is 100% or the food intake is less than 10% based on the ratio of the vehicle control area, and it is effective.

(2) Effectiveness test against Spodoptera litura The emulsion (I) was diluted with water so that the concentration of the compound of the present invention became 125 ppm. The cabbage leaves were immersed in the diluent for 30 seconds. The cabbage leaf was air-dried and put into a petri dish, and 5 second-instar larvae of Spodoptera litura were placed. Place the petri dish in a constant temperature room with a temperature of 25°C and a humidity of 60%. When 6 days have passed after the injection, a life-or-death determination is made and the insecticidal rate is calculated. The test was repeated twice.

The compound number a-1, compound number a-4, compound number e-4, compound number e-22, and compound number f-1 were tested for efficacy against Spodoptera litura. Any compound showed an insecticidal rate of more than 80%.

(3) Effect test on cotton bollworm (Helicoverpa armigera) The emulsion (I) was diluted with water so that the concentration of the compound of the present invention became 125 ppm. The cabbage leaves were immersed in the diluent for 30 seconds. The cabbage leaf was air-dried and put into a petri dish, and 5 second-instar larvae of cotton bollworm were put. Place the petri dish in a constant temperature room with a temperature of 25°C and a humidity of 60%. When 6 days have passed after the injection, a life-or-death determination is made and the insecticidal rate is calculated. The test was repeated twice.

For the compounds of compound number a-4, compound number e-2, compound number e-4, compound number e-5, and compound number f-1, an efficacy test against Helicoverpa armigera was performed. Any compound showed an insecticidal rate of more than 80%.

(4) Efficacy test against Tetranychus kanzawai (Tetranychus kanzawai) Mung bean seedlings were cultivated in a 3-inch pot, and 5 female adults of Tetranychus Kanzawa were inoculated on the primary leaves. The emulsion (I) was diluted with water so that the concentration of the compound of the present invention became 125 ppm. Spread the diluent on the mung beans and set it as a treatment zone. In addition, except for removing the compound of the present invention from Emulsion (I), the test was conducted under the same conditions and set as a vehicle control zone. The 3-inch pot was placed in a constant temperature room with a temperature of 25°C and a humidity of 65%. After 4 days of spreading, the inoculated female adults of Tetranychus Kanzawa were removed, leaving only the leaves that were born on the leaves. egg. At 11 days after spreading, the number of individuals living on the leaf was investigated, and the control rate was calculated according to the following formula. The test was repeated twice. Control rate (%)=100×[1-Nt/Nc] Nt: number of surviving individuals in the treatment area, Nc: number of surviving individuals in the vehicle control area

For compound number a-1, compound number e-3, compound number e-5, compound number e-6, compound number e-16, compound number e-22, compound number e-23, compound number e-25, compound The compounds No. e-26 and compound No. f-1 were tested for efficacy against Tetranychus Kanzawa. Any compound showed a control rate of more than 90%.

(5) Effect test on Tetranychus urticae Raise bean seedlings in a 3-inch pot and inoculate 5 female adults of Tetranychus urticae on primary leaves. The emulsion (I) was diluted with water so that the concentration of the compound of the present invention became 125 ppm. Spread the diluent on the kidney beans and set it as a treatment zone. In addition, except for removing the compound of the present invention from Emulsion (I), the test was conducted under the same conditions and set as a vehicle control zone. The 3-inch pot is placed in a constant temperature room with a temperature of 25°C and a humidity of 65%. When 3 days have passed after spreading, the inoculated female adults of Tetranychus urticae are removed, leaving only the eggs laid on the leaves. . At the point of 10 days after the spreading, the number of individuals living on the leaf was investigated, and the control rate was calculated according to the following formula. The test was repeated twice. Control rate (%)=100×[1-Nt/Nc] Nt: number of surviving individuals in the treatment area, Nc: number of surviving individuals in the vehicle control area

For the compounds of compound number e-7, compound number e-8, compound number e-9 and compound number e-10, an efficacy test against Tetranychus urticae was performed. Any compound showed a control rate of more than 90%.

(6) Effect test on cotton aphid (Aphis gossypii) Plant cucumbers in 3-inch pots. The female adults of cotton aphid were put on cucumbers 10 days after germination. On the second day, the first instar larvae produced were left, and the female adults were removed. The emulsion (I) was diluted with water so that the concentration of the compound of the present invention became 125 ppm. Spread the diluent on the cucumber. Then, the cucumber was placed in a constant temperature room with a temperature of 25°C and a humidity of 60%. After 5 days, the life and death of the cotton aphid was studied, and the insecticidal rate was determined.

For the compounds of compound number e-10, compound number e-23, compound number e-25 and compound number e-26, the efficacy test against cotton aphid was carried out. The insecticidal rate of any compound is more than 80%.

The compound selected at random from the pyridinium salt of the present invention exerts the above-mentioned effects. Therefore, it can be understood that the pyridinium salt of the present invention, including the compounds not completely shown in the examples, has harmful biological control, Compounds that kill mites, especially insects.

Claims (5)

A compound represented by formula (I) or formula (II);

(In formula (I) and formula (II), A represents an oxygen atom or a sulfur atom, X ¹ represents a halogen group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkene Group, substituted or unsubstituted C2-6 alkynyl, substituted or unsubstituted C1-6 alkoxy, substituted or unsubstituted C2-6 alkenyloxy, substituted or unsubstituted C2-6 alkynyloxy, substituted or unsubstituted C1-6 alkylcarbonyl, substituted or unsubstituted C1-6 alkoxycarbonyl, substituted or unsubstituted C1-6 alkylthio, A substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C3-8 cycloalkyl group, Unsubstituted C6-10 aryl groups, substituted or unsubstituted C6-10 aryloxy groups, substituted or unsubstituted 5- to 6-membered heteroaryl groups, substituted or unsubstituted 5-membered to 6-membered heteroaryloxy group, group represented by ^Ra R ^b N-, group represented by ^Ra R ^b N-CO-, group represented by R ^c CO-NH-, pentafluoro Hydrosulfide, nitro or cyano, R ^a represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R ^b represents a hydrogen atom, A substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R ^c represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C1-6 alkyl group A substituted C6-10 aryl group, m represents ^{the number of X 1} and is any integer of 0-5, Y represents a substituted or unsubstituted C1-6 alkylene group, and a substituted or unsubstituted C2- 6 alkynylene or substituted or unsubstituted C3-6 cycloalkylene, X ² represents substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl, Substituted or unsubstituted C2-6 alkynyl, hydroxyl, substituted or unsubstituted C1-6 alkoxy, substituted or unsubstituted C2-6 alkenyloxy, substituted or unsubstituted C2-6 alkynyloxy, substituted or unsubstituted C1-6 alkylcarbonyl, substituted or unsubstituted C1-6 alkoxycarbonyl, substituted or unsubstituted C1-6 alkylthio, A substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C3-8 cycloalkyl group, Unsubstituted C6-10 aryl groups, substituted or unsubstituted C6-10 aryloxy groups, substituted or unsubstituted 5- to 6-membered heteroaryl groups, substituted or unsubstituted 5-membered to 6-membered heteroaryloxy group, group ^{represented by R a1} R ^b1 N-, group represented by R ^a1 R ^b1 N-CO-, group represented by R ^c1 CO-NH-, pentafluoro Hydrosulfide, nitro or cyano, R ^a1 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R ^b1 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R ^c1 represents a hydrogen atom, substituted or unsubstituted A substituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, X ³ represents a halogen group, a substituted or unsubstituted C1-6 alkyl group, a hydroxy group, a substituted or unsubstituted C1-6 alkoxy, substituted or unsubstituted C1-6 alkylthio, substituted or unsubstituted C1-6 alkylsulfinyl, substituted or unsubstituted C1-6 alkyl Sulfonyl, pentafluorohydrosulfide, nitro or cyano, n represents ^{the number of X 3} and is any integer from 0 to 4, Z ^q- represents a counter ion, and q represents the valence of the counter ion and is 1 or 2). A pest control agent containing at least one selected from the compounds described in claim 1 as an active ingredient. An insecticide or acaricide containing at least one compound selected from the compounds described in claim 1 as an active ingredient. An ectoparasite control agent containing at least one selected from the compounds described in claim 1 as an active ingredient. An internal parasite control or repellent containing at least one selected from the compounds described in claim 1 as an active ingredient.