Patent Publication Number: US-2022213039-A1

Title: Pyridinium salts and pest control agent

Description:
TECHNICAL FIELD 
     The present invention relates to a pyridinium salt and a pest control agent. More specifically, the present invention relates to a pyridinium salt which has excellent insecticidal activity and/or acaricidal activity, is excellent in safety and can be synthesized in an industrially favorable manner, and a pest control agent containing this pyridinium salt as an active ingredient. 
     Priority is claimed on Japanese Patent Application No. 2019-100656 and Japanese Patent Application No. 2019-100653, filed May 29, 2019, the contents of which are incorporated herein by reference. 
     BACKGROUND ART 
     Various compounds having insecticidal/acaricidal activity have been proposed. In order to put such a compound to practical use as an agricultural chemical, it is required not only to have sufficiently high efficacy, but also to be unlikely to cause drug resistance, not to cause phytotoxicity to plants or soil pollution, and to have low toxicity to livestock and fish, or the like. 
     Incidentally, Patent Document 1 discloses a compound represented by a formula 
     (A) having acaricidal activity, and the like. 
     
       
         
         
             
             
         
       
     
     Further, Non-Patent Document 1 discloses a compound represented by a formula (B) having analgesic activity, and the like. 
     
       
         
         
             
             
         
       
     
     CITATION LIST 
     Patent Document 
     
         
         [Patent Document 1] U.S. Pat. No. 4,138,548 
       
    
     Non-Patent Document 
     
         
         [Non-Patent Document 1] Journal of Medicinal Chemistry, 1982, vol. 25, p 720-723 
       
    
     SUMMARY OF INVENTION 
     Technical Problem 
     An object of the present invention is to provide a pyridinium salt which is excellent in pest control activity, in particular, insecticidal activity and/or acaricidal activity, excellent in safety and can be synthesized in an industrially favorable manner. Another object of the present invention is to provide a pest control agent, an insecticidal or acaricidal agent, an ectoparasite control agent, or an endoparasite control- or exterminating agent containing a pyridinium salt as an active ingredient. 
     Solution to Problem 
     As a result of intensive studies in order to solve the above problems, the present invention including the following embodiments has been completed. 
     [1] A compound represented by a formula (I) or a formula (II): 
     
       
         
         
             
             
         
       
     
     (in the formulas (I) and (II), 
     A represents an oxygen atom or a sulfur atom; 
     X 1  represents a halogeno group, a substituted or unsubstituted C 1-6  alkyl group, a substituted or unsubstituted C 2-6  alkenyl group, a substituted or unsubstituted C 2-6  alkynyl group, a substituted or unsubstituted C 1-6  alkoxy group, a substituted or unsubstituted C 2-6  alkenyloxy group, a substituted or unsubstituted C 2-6  alkynyloxy group, a substituted or unsubstituted C 1-6  alkylcarbonyl group, a substituted or unsubstituted C 1-6  alkoxycarbonyl group, a substituted or unsubstituted C 1-6  alkylthio group, a substituted or unsubstituted C 1-6  alkylsulfinyl group, a substituted or unsubstituted C 1-6  alkylsulfonyl group, a substituted or unsubstituted C 3-8  cycloalkyl group, a substituted or unsubstituted C 6-10  aryl group, a substituted or unsubstituted C 6-10  aryloxy group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, a substituted or unsubstituted 5- to 6-membered heteroaryloxy group, a group represented by R a R b N—, a group represented by R a R b N—CO—, a group represented by R c CO—NH—, a pentafluorosulfanyl group, a nitro group or a cyano group; 
     R a  represents a hydrogen atom, a substituted or unsubstituted C 1-6  alkyl group, or a substituted or unsubstituted C 6-10  aryl group, 
     R b  represents a hydrogen atom, a substituted or unsubstituted C 1-6  alkyl group, or a substituted or unsubstituted C 6-10  aryl group, 
     R c  represents a hydrogen atom, a substituted or unsubstituted C 1-6  alkyl group, or a substituted or unsubstituted C 6-10  aryl group, 
     m represents the number of X 1  groups and is any integer of 0 to 5; and 
     Z represents a group represented by a formula (Z-1) or a formula (Z-2), 
     
       
         
         
             
             
         
       
     
     a bond marked with a symbol * means a bond with a carbonyl group or a thiocarbonyl group in a pyridinium salt, 
     Y represents a substituted or unsubstituted C 2-6  alkenylene group, 
     Q represents a naphthalene ring or a 6- to 10-membered heteroaryl ring, 
     X 2  represents a substituted or unsubstituted C 1-6  alkyl group, a substituted or unsubstituted C 2-6  alkenyl group, a substituted or unsubstituted C 2-6  alkynyl group, a hydroxyl group, a substituted or unsubstituted C 1-6  alkoxy group, a substituted or unsubstituted C 2-6  alkenyloxy group, a substituted or unsubstituted C 2-6  alkynyloxy group, a substituted or unsubstituted C 1-6  alkylcarbonyl group, a substituted or unsubstituted C 1-6  alkoxycarbonyl group, a substituted or unsubstituted C 1-6  alkylthio group, a substituted or unsubstituted C 1-6  alkylsulfinyl group, a substituted or unsubstituted C 1-6  alkylsulfonyl group, a substituted or unsubstituted C 3-8  cycloalkyl group, a substituted or unsubstituted C 6-10  aryloxy group, a substituted or unsubstituted 5- to 6-membered heteroaryloxy group, a group represented by R a1 R b1 N—, a group represented by R a1 R b1 N—CO—, a group represented by R c1 CO—NH—, a group represented by R d1 O—N═CR f1 —, a pentafluorosulfanyl group, a nitro group or a cyano group, 
     R a1  represents a hydrogen atom, a substituted or unsubstituted C 1-6  alkyl group, or a substituted or unsubstituted C 6-10  aryl group, 
     R b1  represents a hydrogen atom, a substituted or unsubstituted C 1-6  alkyl group, or a substituted or unsubstituted C 6-10  aryl group, 
     R c1  represents a hydrogen atom, a substituted or unsubstituted C 1-6  alkyl group, or a substituted or unsubstituted C 6-10  aryl group, 
     R d1  represents a hydrogen atom or a substituted or unsubstituted C 1-6  alkyl group, 
     R f1  represents a hydrogen atom or a substituted or unsubstituted C 1-6  alkyl group, 
     X 3  represents a halogeno group, a substituted or unsubstituted C 1-6  alkyl group, a hydroxyl group, a substituted or unsubstituted C 1-6  alkoxy group, a substituted or unsubstituted C 1-6  alkylthio group, a substituted or unsubstituted C 1-6  alkylsulfinyl group, a substituted or unsubstituted C 1-6  alkylsulfonyl group, a pentafluorosulfanyl group, a nitro group, or a cyano group, 
     n represents the number of X 3  groups and is any integer of 0 to 4, 
     Z q−  represents a counter ion, and 
     q represents a valence of the counter ion and is 1 or 2.) 
     [2] The compound according to the above [1], wherein the compound represented by the formula (I) is a compound represented by a formula (I-1) and the compound represented by the formula (II) is a compound represented by a formula (II-1). 
     
       
         
         
             
             
         
       
     
     (In the formula (I-1) and formula (II-1), 
     A, X 1 , m, Y, X 2 , X 3 , n, Z q− , and q have the same meanings as those defined in the above [1].) 
     [3] The compound according to the above [1], wherein the compound represented by the formula (I) is a compound represented by a formula (I-2) and the compound represented by the formula (II) is a compound represented by a formula (II-2). 
     
       
         
         
             
             
         
       
     
     (In the formula (I-2) and formula (II-2), 
     A, X 1 , m, Q, X 2 , X 3 , n, Z q− , and q have the same meanings as those defined in the above [1].) 
     [4] A pest control agent containing at least one selected from the compounds according to any one of the above [1] to [3] as an active ingredient. 
     [5] An insecticidal or acaricidal agent containing at least one selected from the compounds according to any one of the above [1] to [3] as an active ingredient. 
     [6] An ectoparasite control agent containing at least one selected from the compounds according to any one of the above [1] to [3] as an active ingredient. 
     [7] An endoparasite control or exterminating agent containing at least one selected from the compounds according to any one of the above [1] to [3] as an active ingredient. 
     Advantageous Effects of Invention 
     The pyridinium salt of the present invention has a function of controlling pests which are problematic in terms of agricultural crops and hygiene. A control agent containing the pyridinium salt of the present invention can effectively control pests, especially agricultural pests and mites and ticks at a lower concentration, and can also effectively control ectoparasites and endoparasites that may harm humans and animals. 
    
    
     DESCRIPTION OF EMBODIMENTS 
     A pyridinium salt of the present invention is a compound represented by a formula (I) (inner salt) or a compound represented by a formula (II) (intermolecular salt). An inner salt is a compound having a cation center and an anion center in one molecule, that is, a zwitterion. An intermolecular salt is a compound formed by ion association of a cation and an anion, that is, an ion pair. 
     
       
         
         
             
             
         
       
     
     Here, the term “unsubstituted” means that it is composed only of a group which becomes a mother nucleus. When it is described only by the name of the group which becomes the mother nucleus without being described as “substituted”, it means “unsubstituted” unless otherwise stated. 
     On the other hand, the term “substituted” means that any hydrogen atom of a group which becomes a mother nucleus is substituted with a group (substituent) having the same or different structure as that of the mother nucleus. Therefore, a “substituent” is another group bonded to a group which becomes a mother nucleus. The number of substituents may be one, or two or more. The two or more substituents may be the same or different. 
     The terms “C 1-6 ” and the like mean that the number of carbon atoms in the group which becomes a mother nucleus 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. 
     A “substituent” is not particularly limited as long as it is chemically acceptable and has the effects of the present invention. Hereinafter, groups which can be a “substituent” are exemplified. 
     A C 1-6  alkyl group such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group, an n-pentyl group, and an n-hexyl group; 
     a C 2-6  alkenyl group such as a vinyl group, a 1-propenyl group, a 2-propenyl group (allyl group), a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, and a 2-methyl-2-propenyl group; 
     a C 2-6  alkynyl group such as an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, and a 1-methyl-2-propynyl group; 
     a C 3-8  cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cubanyl group; 
     a C 6-10  aryl group such as a phenyl group and a naphthyl group; 
     a C 6-10  aryl C 1-6  alkyl group such as a benzyl group and a phenethyl group; 
     a 3- to 6-membered heterocyclyl group; 
     a 3- to 6-membered heterocyclyl C 1-6  alkyl group; 
     a hydroxyl group; 
     a C 1-6  alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, and a t-butoxy group; 
     a C 2-6  alkenyloxy group such as a vinyloxy group, an allyloxy group, a propenyloxy group, and a butenyloxy group; 
     a C 2-6  alkynyloxy group such as an ethynyloxy group and a propargyloxy group; 
     a C 6-10  aryloxy group such as a phenoxy group and a naphthoxy group; 
     a C 6-10  aryl C 1-6  alkoxy group such as a benzyloxy group and a phenethyloxy group; 
     a 5- to 6-membered heteroaryloxy group such as a thiazolyloxy group and a pyridyloxy group; 
     a 5- to 6-membered heteroaryl C 1-6  alkyloxy group such as a thiazolylmethyloxy group and a pyridylmethyloxy group; 
     a formyl group; 
     a C 1-6  alkylcarbonyl group such as an acetyl group and a propionyl group; 
     a formyloxy group; 
     a C 1-6  alkylcarbonyloxy group such as an acetyloxy group and a propionyloxy group; 
     a C 6-10  arylcarbonyl group such as a benzoyl group; 
     a C 1-6  alkoxycarbonyl group such as a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group and a t-butoxycarbonyl group; 
     a C 1-6  alkoxycarbonyloxy group such as a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an n-propoxycarbonyloxy group, an i-propoxycarbonyloxy group, an n-butoxycarbonyloxy group and a t-butoxycarbonyloxy group; 
     a carboxyl group; 
     a halogeno group such as a fluoro group, a chloro group, a bromo group, and an iodo group; 
     a C 1-6  haloalkyl group such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a 1,2-dichloro-n-propyl group and a 1-fluoro-n-butyl group; 
     a C 2-6  haloalkenyl group such as a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group; 
     a C 2-6  haloalkynyl group such as a 4,4-dichloro-1-butynyl group, a 4-fluoro-1-pentynyl group, and a 5-bromo-2-pentynyl group; 
     a C 1-6  haloalkoxy group such as a trifluoromethoxy group, a 2-chloro-n-propoxy group, and a 2,3-dichlorobutoxy group; 
     a C 2-6  haloalkenyloxy group such as a 2-chloropropenyloxy group and a 3-bromobutenyloxy group; 
     a C 1-6  haloalkylcarbonyl group such as a chloroacetyl group, a trifluoroacetyl group and a trichloroacetyl group; 
     an amino group; 
     a C 1-6  alkyl-substituted amino group such as a methylamino group, a dimethylamino group and a diethylamino group; 
     a C 6-10  arylamino group such as an anilino group and a naphthylamino group; 
     a C 6-10  aryl C 1-6  alkylamino group such as a benzylamino group and a phenethylamino group; 
     a formylamino group; 
     a C 1-6  alkylcarbonylamino group such as an acetylamino group, a propanoylamino group, a butyrylamino group and an i-propylcarbonylamino group; 
     a C 1-6  alkoxycarbonylamino group such as a methoxycarbonylamino group, an ethoxycarbonylamino group, an n-propoxycarbonylamino group and an i-propoxycarbonylamino group; 
     an unsubstituted or substituted aminocarbonyl group such as an aminocarbonyl group, a dimethylaminocarbonyl group, a phenylaminocarbonyl group and an N-phenyl-N-methylaminocarbonyl group; 
     an imino C 1-6  alkyl group such as an iminomethyl group, a (1-imino)ethyl group and a (1-imino)-n-propyl group; 
     a substituted or unsubstituted N-hydroxyimino C 1-6  alkyl group such as an N-hydroxy-iminomethyl group, a (1-(N-hydroxy)-imino)ethyl group, a (1-(N-hydroxy)-imino)propyl group, an N-methoxy-iminomethyl group, and a (1-(N-methoxy)-imino)ethyl group; 
     an aminocarbonyloxy group; 
     a C 1-6  alkyl-substituted aminocarbonyloxy group such as an ethylaminocarbonyloxy group and a dimethylaminocarbonyloxy group; 
     a mercapto group; 
     a C 1-6  alkylthio group such as a methylthio group, an ethylthio group, an n-propylthio group, an i-propylthio group, an n-butylthio group, an i-butylthio group, an s-butylthio group and a t-butylthio group; 
     a C 1-6  haloalkylthio group such as a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group; 
     a C 6-10  arylthio group such as a phenylthio group and a naphthylthio group; 
     a 5- to 6-membered heteroarylthio group such as a thiazolylthio group and a pyridylthio group; 
     a C 1-6  alkylsulfinyl group such as a methylsulfinyl group, an ethylsulfinyl group and a t-butylsulfinyl group; 
     a C 1-6  haloalkylsulfinyl group such as a trifluoromethylsulfinyl group and a 2,2,2-trifluoroethylsulfinyl group; 
     a C 6-10  arylsulfinyl group such as a phenylsulfinyl group; 
     a 5- to 6-membered heteroarylsulfinyl group such as a thiazolylsulfinyl group and a pyridylsulfinyl group; 
     a C 1-6  alkylsulfonyl group such as a methylsulfonyl group, an ethylsulfonyl group and a t-butylsulfonyl group; 
     a C 1-6  haloalkylsulfonyl group such as a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group; 
     a C 6-10  arylsulfonyl group such as a phenylsulfonyl group; 
     a 5- to 6-membered heteroarylsulfonyl group such as a thiazolylsulfonyl group and a pyridylsulfonyl group; 
     a C 1-6  alkylsulfonyloxy group such as a methylsulfonyloxy group, an ethylsulfonyloxy group and a t-butylsulfonyloxy group; 
     a C 1-6  haloalkylsulfonyloxy group such as a trifluoromethylsulfonyloxy group and a 2,2,2-trifluoroethylsulfonyloxy group; 
     a tri C 1-6  alkyl-substituted silyl group such as a trimethylsilyl group, a triethylsilyl group and a t-butyldimethylsilyl group; 
     a tri C 6-10  aryl-substituted silyl group such as a triphenylsilyl group; 
     a pentafluorosulfanyl group; 
     a cyano group; a nitro group. 
     Further, in these “substituents”, any hydrogen atom in the substituent may be substituted with a group having a different structure. Examples of the “substituent” in this case include a C 1-6  alkyl group, a C 1-6  haloalkyl group, a C 1-6  alkoxy group, a C 1-6  haloalkoxy group, a halogeno group, a cyano group and a nitro group. 
     Further, the above-described “3- to 6-membered heterocyclyl group” includes 1 to 4 hetero atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as constituent atoms of the ring. The heterocyclyl group may be either monocyclic or polycyclic. As long as the polycyclic heterocyclyl group includes at least one heterocyclic ring, the remaining ring may be any of a saturated alicyclic ring, an unsaturated alicyclic ring or an aromatic ring. Examples of the “3- to 6-membered heterocyclyl group” include a 3- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, and a 5- to 6-membered partially unsaturated heterocyclyl group. 
     Examples of the 3- to 6-membered saturated heterocyclyl group include an aziridinyl group, an epoxy group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group. 
     Examples of the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group. 
     Examples of the 6-membered heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group. 
     In the formula (II), Z q−  represents a counter ion, and q represents a valence of the counter ion and is 1 or 2. Specific examples of a monovalent anion Z −  include Cl − , Br − , I − , NO 3   − , CH 3 COO − , CH 3 SO 3   − , CF 3 SO 3   −  and TolSO 3   − . Specific examples of a divalent anion Z 2−  include SO 4   2−  and the like. Tol is an abbreviation indicating an o-methylphenyl group, an m-methylphenyl group or a p-methylphenyl group. 
     [A] 
     In the formulas (I) and (II), A represents an oxygen atom or a sulfur atom. 
     In the present invention, A is preferably an oxygen atom. 
     [X 1 , m] 
     In the formulas (I) and (II), X 1  represents a halogeno group, a substituted or unsubstituted C 1-6  alkyl group, a substituted or unsubstituted C 2-6  alkenyl group, a substituted or unsubstituted C 2-6  alkynyl group, a substituted or unsubstituted C 1-6  alkoxy group, a substituted or unsubstituted C 2-6  alkenyloxy group, a substituted or unsubstituted C 2-6  alkynyloxy group, a substituted or unsubstituted C 1-6  alkylcarbonyl group, a substituted or unsubstituted C 1-6  alkoxycarbonyl group, a substituted or unsubstituted C 1-6  alkylthio group, a substituted or unsubstituted C 1-6  alkylsulfinyl group, a substituted or unsubstituted C 1-6  alkylsulfonyl group, a substituted or unsubstituted C 3-8  cycloalkyl group, a substituted or unsubstituted C 6-10  aryl group, a substituted or unsubstituted C 6-10  aryloxy group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, a substituted or unsubstituted 5- to 6-membered heteroaryloxy group, a group represented by R a R b N—, a group represented by R a R b N—CO—, a group represented by R c CO—NH—, a pentafluorosulfanyl group, a nitro group or a cyano group; and m represents the number of X 1  groups and is any integer of 0 to 5. When m is 2 or more, X 1  groups may be the same or different from each other. 
     As the “halogeno group” represented by X 1 , a fluoro group, a chloro group, a bromo group, an iodo group and the like can be mentioned. 
     The “C 1-6  alkyl group” represented by X 1  may be linear or branched. Examples of the “C 1-6  alkyl group” represented by X 1  include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, a 2,2-dimethylpropyl group and an i-hexyl group. 
     Examples of the “C 2-6  alkenyl group” represented by X 1  include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-methyl-2-butenyl group, a 2-methyl-2-butenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group and a 5-hexenyl group. 
     Examples of the “C 2-6  alkynyl group” represented by X 1  include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-methyl-2-propynyl group, a 2-methyl-3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a 2-methyl-3-pentynyl group, a 1-hexynyl group and a 1,1-dimethyl-2-butynyl group. 
     Examples of the “C 1-6  alkoxy group” represented by X 1  include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, an i-butoxy group, an s-butoxy group, a t-butoxy group and an i-hexyloxy group. 
     Examples of the “C 2-6  alkenyloxy group” represented by X 1  include a vinyloxy group, an allyloxy group, a propenyloxy group and a butenyloxy group. 
     Examples of the “C 2-6  alkynyloxy group” represented by X 1  include an ethynyloxy group and a propargyloxy group. 
     Examples of the “C 1-6  alkylcarbonyl group” represented by X 1  include an acetyl group and a propionyl group. 
     Examples of the “C 1-6  alkoxycarbonyl group” represented by X 1  include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group and a t-butoxycarbonyl group. 
     Examples of the “C 1-6  alkylthio group” represented by X 1  include a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group and an i-propylthio group. 
     Examples of the “C 1-6  alkylsulfinyl group” represented by X 1  include a methylsulfinyl group, an ethylsulfinyl group and a t-butylsulfinyl group. 
     Examples of the “C 1-6  alkylsulfonyl group” represented by X 1  include a methylsulfonyl group, an ethylsulfonyl group and a t-butylsulfonyl group. 
     As the substituent on the “C 1-6  alkyl group”, “C 2-6  alkenyl group”, “C 2-6  alkynyl group”, “C 1-6  alkoxy group”, “C 2-6  alkenyloxy group”, “C 2-6  alkynyloxy group”, “C 1-6  alkylcarbonyl group”, “C 1-6  alkoxycarbonyl group”, “C 1-6  alkylthio group”, “C 1-6  alkylsulfinyl group” or “C 1-6  alkylsulfonyl group” represented by X 1 , a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; a hydroxyl group; a C 1-6  alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group and a t-butoxy group; a C 1-6  haloalkoxy group such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group and a trifluoromethoxy group; a C 6-10  aryl group such as a phenyl group and a naphthyl group; or a cyano group; is preferable. 
     Examples of the “C 3-8  cycloalkyl group” represented by X 1  include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and a cycloheptyl group. 
     Examples of the “C 6-10  aryl group” represented by X 1  include a phenyl group and a naphthyl group. 
     Examples of the “C 6-10  aryloxy group” represented by X 1  include a phenoxy group and a naphthoxy group. 
     The “5- to 6-membered heteroaryl group” represented by X 1  contains 1, 2, 3 or 4 hetero atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as constituent atoms of the ring. When there are two or more hetero atoms, they may be the same or different. 
     Examples of the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group, and examples of the 6-membered heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group. 
     The “5- to 6-membered heteroaryloxy group” represented by X 1  has a structure in which a 5- or 6-membered heteroaryl group and an oxy group are bonded. Specific examples thereof include a thiazolyloxy group and a pyridyloxy group. 
     As the substituent on the “C 3-8  cycloalkyl group”, “C 6-10  aryl group”, “C 6-10  aryloxy group”, “5- to 6-membered heteroaryl group”, or “5- to 6-membered heteroaryloxy group” represented by X 1 , a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; a C 1-6  alkyl group such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group, an n-pentyl group and an n-hexyl group; a C 1-6  haloalkyl group such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a 1,2-dichloro-n-propyl group and a 1-fluoro-n-butyl group; a hydroxyl group; a C 1-6  alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group and a t-butoxy group; a C 1-6  haloalkoxy group such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group and a trifluoromethoxy group; or a cyano group; is preferable. 
     In the “group represented by R a R b N—” or “group represented by R a R b N—CO—” represented by X 1 , R a  represents a hydrogen atom, a substituted or unsubstituted C 1-6  alkyl group, or a substituted or unsubstituted C 6-10  aryl group, and R b  represents a hydrogen atom, a substituted or unsubstituted C 1-6  alkyl group, or a substituted or unsubstituted C 6-10  aryl group. 
     The “C 1-6  alkyl group” represented by R a  or R b  may be linear or branched. Examples of the “C 1-6  alkyl group” represented by R a  or R b  include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, a 2,2-dimethylpropyl group and an i-hexyl group. As the substituent on the “C 1-6  alkyl group”, a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; a hydroxyl group; a C 1-6  alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group and a t-butoxy group; a C 1-6  haloalkoxy group such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group and a trifluoromethoxy group; a C 6-10  aryl group such as a phenyl group and a naphthyl group; or a cyano group; is preferable. 
     Examples of the “C 6-10  aryl group” represented by R a  or R b  include a phenyl group and a naphthyl group. As the substituent on the “C 6-10  aryl group”, a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; a C 1-6  alkyl group such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group, an n-pentyl group and an n-hexyl group; a C 1-6  haloalkyl group such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a 1,2-dichloro-n-propyl group and a 1-fluoro-n-butyl group; a hydroxyl group; a C 1-6  alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group and a t-butoxy group; a C 1-6  haloalkoxy group such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group and a trifluoromethoxy group; or a cyano group; is preferable. 
     In the “group represented by R c CO—NH—” represented by X 1 , R c  represents a hydrogen atom, a substituted or unsubstituted C 1-6  alkyl group, or a substituted or unsubstituted C 6-10  aryl group. 
     The “C 1-6  alkyl group” represented by R c  may be linear or branched. Examples of the “C 1-6  alkyl group” represented by R include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, a 2,2-dimethylpropyl group and an i-hexyl group. As the substituent on the “C 1-6  alkyl group”, a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; a hydroxyl group; a C 1-6  alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group and a t-butoxy group; a C 1-6  haloalkoxy group such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group and a trifluoromethoxy group; a C 6-10  aryl group such as a phenyl group and a naphthyl group; or a cyano group; is preferable. 
     Examples of the “C 6-10  aryl group” represented by R c  include a phenyl group and a naphthyl group. As the substituent on the “C 6-10  aryl group”, a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; a C 1-6  alkyl group such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group, an n-pentyl group and an n-hexyl group; a C 1-6  haloalkyl group such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a 1,2-dichloro-n-propyl group and a 1-fluoro-n-butyl group; a hydroxyl group; a C 1-6  alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group and a t-butoxy group; a C 1-6  haloalkoxy group such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group and a trifluoromethoxy group; or a cyano group; is preferable. 
     In the present invention, X 1  is preferably a halogeno group, a halogeno group-substituted or unsubstituted C 1-6  alkyl group, or a halogeno group-substituted or unsubstituted C 1-6  alkoxy group. 
     Examples of the “halogeno group-substituted C 1-6  alkyl group” represented by X 1  include a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group and a 2,2,2,1,1-pentafluoroethyl group. 
     Examples of the “halogeno group-substituted C 1-6  alkoxy group” represented by X 1  include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,1,1-tetrafluoroethoxy group and a 2,2,2,1,1-pentafluoroethoxy group. 
     [Z] 
     Z represents a group represented by the following formula (Z-1) or formula (Z-2). 
     
       
         
         
             
             
         
       
     
     A bond marked with a symbol * means a bond with a carbonyl group or a thiocarbonyl group in a pyridinium salt. 
     [Y] 
     Y represents a substituted or unsubstituted C 2-6  alkenylene group. 
     Examples of the “C 2-6  alkenylene group” represented by Y include a vinylene group (—CH═CH—), a divinylene group (—CH═CH—CH═CH—), and a propenylene group (—CH═CH—CH 2 —, —CH 2 —CH═CH—). 
     As the substituent on the “C 2-6  alkenylene group” represented by Y, a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; a C 1-6  alkyl group such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group and a t-butyl group; a C 2-6  alkynyl group such as an ethynyl group; a C 1-6  haloalkyl group such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a 1,2-dichloro-n-propyl group and a 1-fluoro-n-butyl group; a hydroxyl group; a C 1-6  alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group and a t-butoxy group; a C 1-6  haloalkoxy group such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group and a trifluoromethoxy group; a C 1-6  alkoxy C 1-6  alkyl group such as a methoxymethyl group; a C 1-6  alkylthio group such as a methylthio group, an ethylthio group, an n-propylthio group, an i-propylthio group, an n-butylthio group, an i-butylthio group, an s-butylthio group and a t-butylthio group; a C 1-6  alkylsulfinyl group such as a methylsulfinyl group, an ethylsulfinyl group and a t-butylsulfinyl group; or a C 1-6  alkylsulfonyl group such as a methylsulfonyl group, an ethylsulfonyl group and a t-butylsulfonyl group; is preferable. 
     [Q] 
     Q represents a naphthalene ring or a 6- to 10-membered heteroaryl ring. 
     Examples of the 6-membered heteroaryl ring include a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, and a triazine ring. 
     Examples of the 9-membered heteroaryl ring include an indole ring, a benzofuran ring, a benzothiophene ring, an indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a benzisoxazole ring, and a benzisothiazole ring. 
     Examples of the 10-membered heteroaryl ring include a quinoline ring, an isoquinoline ring, a cinnoline ring, a phthalazine ring, a quinazoline ring, and a quinoxaline ring. 
     [X 2 ] 
     X 2  represents a substituted or unsubstituted C 1-6  alkyl group, a substituted or unsubstituted C 2-6  alkenyl group, a substituted or unsubstituted C 2-6  alkynyl group, a hydroxyl group, a substituted or unsubstituted C 1-6  alkoxy group, a substituted or unsubstituted C 2-6  alkenyloxy group, a substituted or unsubstituted C 2-6  alkynyloxy group, a substituted or unsubstituted C 1-6  alkylcarbonyl group, a substituted or unsubstituted C 1-6  alkoxycarbonyl group, a substituted or unsubstituted C 1-6  alkylthio group, a substituted or unsubstituted C 1-6  alkylsulfinyl group, a substituted or unsubstituted C 1-6  alkylsulfonyl group, a substituted or unsubstituted C 3-8  cycloalkyl group, a substituted or unsubstituted C 6-10  aryloxy group, a substituted or unsubstituted 5- to 6-membered heteroaryloxy group, a group represented by R a1 R b1 N—, a group represented by R a1 R b1 N—CO—, a group represented by R c1 CO—NH—, a group represented by R d1 O—N═CR f1 —, a pentafluorosulfanyl 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—” represented by X 2 , R a1  represents a hydrogen atom, a substituted or unsubstituted C 1-6  alkyl group, or a substituted or unsubstituted C 6-10  aryl group, and R b1  represents a hydrogen atom, a substituted or unsubstituted C 1-6  alkyl group, or a substituted or unsubstituted C 6-10  aryl group. 
     The “C 1-6  alkyl group” represented by R a1  or R b1  may be linear or branched. Examples of the “C 1-6  alkyl group” represented by R a1  or R b1  include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, a 2,2-dimethylpropyl group and an i-hexyl group. As the substituent on the “C 1-6  alkyl group”, a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; a hydroxyl group; a C 1-6  alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group and a t-butoxy group; a C 1-6  haloalkoxy group such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group and a trifluoromethoxy group; a C 6-10  aryl group such as a phenyl group and a naphthyl group; or a cyano group; is preferable. 
     Examples of the “C 6-10  aryl group” represented by R a1  or R b1  include a phenyl group and a naphthyl group. As the substituent on the “C 6-10  aryl group”, a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; a C 1-6  alkyl group such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group, an n-pentyl group and an n-hexyl group; a C 1-6  haloalkyl group such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a 1,2-dichloro-n-propyl group and a 1-fluoro-n-butyl group; a hydroxyl group; a C 1-6  alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group and a t-butoxy group; a C 1-6  haloalkoxy group such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group and a trifluoromethoxy group; or a cyano group; is preferable. 
     In the “group represented by R c1 CO—NH—” represented by X 2 , R c1  represents a hydrogen atom, a substituted or unsubstituted C 1-6  alkyl group, or a substituted or unsubstituted C 6-10  aryl group. 
     The “C 1-6  alkyl group” represented by R c1  may be linear or branched. Examples of the “C 1-6  alkyl group” represented by R c1  include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, a 2,2-dimethylpropyl group and an i-hexyl group. As the substituent on the “C 1-6  alkyl group”, a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; a hydroxyl group; a C 1-6  alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group and a t-butoxy group; a C 1-6  haloalkoxy group such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group and a trifluoromethoxy group; a C 6-10  aryl group such as a phenyl group and a naphthyl group; or a cyano group; is preferable. 
     Examples of the “C 6-10  aryl group” represented by R c1  include a phenyl group and a naphthyl group. As the substituent on the “C 6-10  aryl group”, a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; a C 1-6  alkyl group such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group, an n-pentyl group and an n-hexyl group; a C 1-6  haloalkyl group such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a 1,2-dichloro-n-propyl group and a 1-fluoro-n-butyl group; a hydroxyl group; a C 1-6  alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group and a t-butoxy group; a C 1-6  haloalkoxy group such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group and a trifluoromethoxy group; or a cyano group; is preferable. 
     In the “group represented by R d1 O—N═CR f1 —” represented by X2, R d1  represents a hydrogen atom or a substituted or unsubstituted C 1-6  alkyl group, and R f1  represents a hydrogen atom or a substituted or unsubstituted C 1-6  alkyl group. 
     The “C 1-6  alkyl groups” represented by R d1  and R f1  may be linear or branched. Examples of the “C 1-6  alkyl groups” represented by R d1  and R f1  include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, a 2,2-dimethylpropyl group and an i-hexyl group. 
     As the substituent on the “C 1-6  alkyl group”, a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; a hydroxyl group; a C 1-6  alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group and a t-butoxy group; a C 1-6  haloalkoxy group such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group and a trifluoromethoxy group; a C 6-10  aryl group such as a phenyl group and a naphthyl group; or a cyano group; is preferable. 
     Examples of the group represented by R d1 O—N═CR f1 — include a (hydroxyimino) methyl group, a (methoxyimino) methyl group, an (ethoxyimino) methyl group, a (methoxyimino) ethyl group, and an (ethoxyimino) ethyl group. 
     As the substituent on the “C 1-6  alkyl group”, a halogeno group is particularly preferable. 
     Specific examples of other groups represented by X 2  include the same as those exemplified for X 1 . 
     In the present invention, X 2  is preferably a halogeno group-substituted or unsubstituted C 1-6  alkyl group, or a halogeno group-substituted or unsubstituted C 1-6  alkoxy group. 
     Examples of the “halogeno group-substituted C 1-6  alkyl group” represented by X 2  include a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group and a 2,2,2,1,1-pentafluoroethyl group. 
     Examples of the “halogeno group-substituted C 1-6  alkoxy group” represented by X 2  include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 2,2,1,1-tetrafluoroethoxy group and a 2,2,2,1,1-pentafluoroethoxy group. 
     [X 3 , n] 
     X 3  represents a halogeno group, a substituted or unsubstituted C 1-6  alkyl group, a hydroxyl group, a substituted or unsubstituted C 1-6  alkoxy group, a substituted or unsubstituted C 1-6  alkylthio group, a substituted or unsubstituted C 1-6  alkylsulfinyl group, a substituted or unsubstituted C 1-6  alkylsulfonyl group, a pentafluorosulfanyl group, a nitro group, or a cyano group; and n represents the number of X 3  groups and is any integer of 0 to 4. 
     Specific examples of these groups represented by X 3  include the same as those exemplified for X 1 . When n is 2 or more, X 3  groups may be the same or different from each other. 
     In the present invention, when Z is a group represented by a formula (Z-1), it can be represented by the following formula (I-1) or formula (II-1). 
     
       
         
         
             
             
         
       
     
     In the formula (I-1) and formula (II-1), A, X 1 , m, Y, X 2 , X 3 , n, Z q− , and q have the same meanings as those defined in the formula (I) or formula (II). 
     In the present invention, when Z is a group represented by a formula (Z-2), it can be represented by the following formula (I-2) or formula (II-2). 
     
       
         
         
             
             
         
       
     
     In the formulas (I-2) and (II-2), A, X 1 , m, Q, X 2 , X 3 , n, Z q− , and q have the same meanings as those defined in the formula (I) or formula (II). 
     The pyridinium salt of the present invention is not particularly limited by the production method thereof. For example, the pyridinium salt of the present invention (hereinafter sometimes referred to as the “compound of the present invention”) can be obtained using a known reaction described in Examples and the like. 
     The compound of the present invention can also be produced, for example, by the following method. 
     [Production of N-Aminopyridinium Salt] 
     
       
         
         
             
             
         
       
     
     An N-aminopyridinium salt (3) can be prepared by reacting a pyridine compound (1) with O-(mesitylsulfonyl) hydroxylamine (2). 
     In addition to O-(mesitylsulfonyl) hydroxylamine, hydroxylamine-O-sulfonic acid, O-(diphenylphosphinyl) hydroxylamine and the like can also be used. 
     
       
         
         
             
             
         
       
     
     The N-aminopyridinium salt (3) can be used as it is for next condensation with a carboxylic acid compound (5), but can be subjected to salt exchange to form an iodide salt and used as an N-aminopyridinium salt (4), when it is necessary to consider the substrate stability. 
     It should be noted that X 1  and m in a reaction formula have the same meanings as those defined in the above formulas (I) and (II). 
     [Condensation Reaction] 
     
       
         
         
             
             
         
       
     
     A compound (6) of the present invention can be produced by condensation of the N-aminopyridinium salt (3) or (4) with the carboxylic acid compound (5) in the presence of a condensing agent used for amide synthesis. 
     Examples of the condensing agent include dicyclohexylcarbodiimide (DCC), diisopropylcarbodiimide (DIC) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (EDI). 
     It should be noted that Z in a reaction formula has the same meanings as those defined in the above formulas (I) and (II). Furthermore, the substituent in Z can be appropriately converted after this condensation reaction. 
     Further, when producing a compound in which A in the above formulas (I) and (II) is sulfur, it can be produced by using a dithiocarboxylic acid ester (7) instead of the carboxylic acid compound (5). 
     
       
         
         
             
             
         
       
     
     In a condensation reaction with the dithiocarboxylic acid ester (7), it is preferable to use a base such as potassium carbonate and sodium ethoxide. 
     It should be noted that R in a reaction formula represents a C 1-6  alkyl group such as a methyl group and an ethyl group. 
     The compound of the present invention is excellent in the effect of controlling harmful organisms such as various agricultural pests affecting the growth of plants, and mites and ticks. 
     In addition, the compound of the present invention is a highly safe substance because it has less phytotoxicity to crops and has low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of an insecticide or acaricide. 
     Furthermore, in recent years, resistance to various existing drugs has developed in a number of insect pests such as diamondback moths, planthoppers, leafhoppers and aphids, causing problems of insufficient efficacy of these drugs, and drugs that are effective even against resistant strains of insect pests have been desired. The compound of the present invention exhibits an excellent controlling effect not only on susceptible strains but also on various resistant strains of insect pests and acaricide-resistant strains of mites and ticks. 
     The compound of the present invention is excellent in the effect of controlling ectoparasites and endoparasites that are harmful to humans and animals. In addition, it is a highly safe substance because it has low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of an agent for controlling ectoparasites and endoparasites. 
     In addition, the compound of the present invention shows efficacy in all developmental stages of organisms to be controlled, and shows an excellent control effect, for example, on eggs, nymphs, larvae, pupae and adults of mites and ticks, insects and the like. 
     [Pest Control Agent, Insecticidal or Acaricidal Agent] 
     The pest control agent or the insecticidal or acaricidal agent of the present invention contains at least one selected from the compounds of the present invention as an active ingredient. The amount of the compound of the present invention contained in the pest control agent or the insecticidal or acaricidal agent of the present invention is not particularly limited as long as it shows the effect of controlling harmful organisms, agricultural pests or mites and ticks, but it is usually preferably within the range of 0.01 to 90 parts by mass, and more preferably within the range of 0.1 to 50 parts by mass, with respect to 100 parts by mass of the control agent, insecticide or acaricide of the present invention. 
     The pest control agent or the insecticidal or acaricidal agent of the present invention is preferably used for plants such as grains; vegetables; root vegetables; potatoes; flowers and ornamental plants; fruit trees; foliage plants and trees of tea, coffee, cacao and the like; pasture grasses; turf grasses; and cotton. 
     In application to plants, the pest control agent or the insecticidal or acaricidal agent of the present invention may be used to any portions of leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, tubers, tuberous roots, shoots, cuttings and the like. 
     Further, the pest control agent or the insecticidal or acaricidal agent of the present invention is not particularly limited by the species of the plant to be applied. Examples of the plant species include an original species, a variant species, an improved variety, a cultivar, a mutant, a hybrid and a genetically modified organism (GMO). 
     The pest control agent of the present invention can be used for seed treatment, foliage application, soil application, water surface application and the like, in order to control various agricultural pests and mites and ticks. 
     Specific examples of various agricultural pests and mites and ticks which can be controlled by the pest control agent of the present invention are shown below. 
     (1) Butterflies or Moths of the Order Lepidoptera 
     (a) Moths of the family Arctiidae such as  Hyphantria cunea  and  Lemyra imparilis;    
     (b) moths of the family Bucculatricidae such as  Bucculatrix pyrivorella;    
     (c) moths of the family Carposinidae such as  Carposina sasakii;    
     (d) moths of the family Crambidae, for example, species belonging to the genus  Diaphania  ( Diaphania  spp.) such as  Diaphania indica  and  Diaphania nitidalis ; for example, species belonging to the genus  Ostrinia  ( Ostrinia  spp.) such as  Ostrinia furnacalis, Ostrinia nubilalis  and  Ostrinia scapulalis ; and others such as  Chilo suppressalis, Cnaphalocrocis medinalis, Conogethes punctiferalis, Diatraea grandiosella, Glyphodes pyloalis, Hellula undalis  and  Parapediasia teterrella;    
     (e) moths of the family Gelechiidae such as  Helcystogramma triannulella, Pectinophora gossypiella, Phthorimaea operculella  and  Sitotroga cerealella;    
     (f) moths of the family Geometridae such as  Ascotis selenaria;    
     (g) moths of the family Gracillariidae such as  Caloptilia theivora, Phyllocnistis citrella  and  Phyllonorycter ringoniella;    
     (h) butterflies of the family Hesperiidae such as  Parnara guttata;    
     (i) moths of the family Lasiocampidae such as  Malacosoma neustria;    
     (j) moths of the family Lymantriidae, for example, species belonging to the genus  Lymantria  ( Lymantria  spp.) such as  Lymantria dispar  and  Lymantria monacha ; and others such as  Euproctis pseudoconspersa  and  Orgyia thyellina;    
     (k) moths of the family Lyonetiidae, for example, species belonging to the genus  Lyonetia  ( Lyonetia  spp.) such as  Lyonetia clerkella  and  Lyonetia prunifoliella malinella;    
     (l) moths of the family Noctuidae, for example, species belonging to the genus  Spodoptera  ( Spodoptera  spp.) such as  Spodoptera depravata, Spodoptera eridania, Spodoptera exigua, Spodoptera frugiperda, Spodoptera littoralis  and  Spodoptera litura ; for example, species belonging to the genus  Autographa  ( Autographa  spp.) such as  Autographa gamma  and  Autographa nigrisigna ; for example, species belonging to the genus  Agrotis  ( Agrotis  spp.) such as  Agrotis ipsilon  and  Agrotis segetum ; for example, species belonging to the genus  Helicoverpa  ( Helicoverpa  spp.) such as  Helicoverpa armigera, Helicoverpa assulta  and  Helicoverpa zea ; for example, species belonging to the genus  Heliothis  ( Heliothis  spp.) such as  Heliothis armigera  and  Heliothis virescens ; and others such as  Aedia leucomelas, Ctenoplusia agnata, Eudocima tyrannus, Mamestra brassicae, Mythimna separata, Naranga aenescens, Panolis japonica, Peridroma saucia, Pseudoplusia includens  and  Trichoplusia ni;    
     (m) moths of the family Nolidae such as  Earias insulana;    
     (n) butterflies of the family Pieridae, for example, species belonging to the genus  Pieris  ( Pieris  spp.) such as  Pieris brassicae  and  Pieris rapae crucivora;    
     (o) moths of the family Plutellidae, for example, species belonging to the genus  Acrolepiopsis  ( Acrolepiopsis  spp.) such as  Acrolepiopsis sapporensis  and  Acrolepiopsis suzukiella ; and others such as  Plutella xylostella;    
     (p) moths of the family Pyralidae such as  Cadra cautella, Elasmopalpus lignosellus, Etiella zinckenella  and  Galleria mellonella;    
     (q) moths of the family Sphingidae, for example, species belonging to the genus  Manduca  ( Manduca  spp.) such as  Manduca quinquemaculata  and  Manduca sexta;    
     (r) moths of the family Stathmopodidae such as  Stathmopoda masinissa;    
     (s) moths of the family Tineidae such as  Tinea translucens;    
     (t) moths of the family Tortricidae, for example, species belonging to the genus  Adoxophyes  ( Adoxophyes  spp.) such as  Adoxophyes honmai  and  Adoxophyes orana ; for example, species belonging to the genus  Archips  ( Archips  spp.) such as  Archips breviplicanus  and  Archips fuscocupreanus ; and others such as  Choristoneura fumiferana, Cydia pomonella, Eupoecilia ambiguella, Grapholitha molesta, Homona magnanima, Leguminivora glycinivorella, Lobesia botrana, Matsumuraeses phaseoli, Pandemis heparana  and  Sparganothis pilleriana ; and 
     (u) moths of the family Yponomeutidae such as  Argyresthia conjugella.    
     (2) Insect Pests of the Order Thysanoptera 
     (a) pests of the family Phlaeothripidae such as  Ponticulothrips diospyrosi ; and 
     (b) pests of the family Thripidae, for example, species belonging to the genus  Frankliniella  ( Frankliniella  spp.) such as  Frankliniella intonsa  and  Frankliniella occidentalis ; for example, species belonging to the genus  Thrips  ( Thrips  spp.) such as  Thrips palmi  and  Thrips tabaci ; and others such as  Heliothrips haemorrhoidalis  and  Scirtothrips dorsalis.    
     (3) Insect Pests of the Order Hemiptera 
     (A) Archaeorrhyncha 
     (a) pests of the family Delphacidae such as  Laodelphax striatella, Nilaparvata lugens, Perkinsiella saccharicida  and  Sogatella furcifera.    
     (B) Clypeorrhyncha 
     (a) pests of the family Cicadellidae, for example, species belonging to the genus  Empoasca  ( Empoasca  spp.) such as  Empoasca fabae, Empoasca nipponica, Empoasca onukii  and  Empoasca sakaii ; and others such as  Arboridia apicalis, Balclutha saltuella, Epiacanthus stramineus, Macrosteles striifrons  and  Nephotettix cinctinceps.    
     (C) Heteroptera 
     (a) pests of the family Alydidae such as  Riptortus clavatus;    
     (b) pests of the family Coreidae such as  Cletus punctiger  and  Leptocorisa chinensis;    
     (c) pests of the family Lygaeidae such as  Blissus leucopterus, Cavelerius saccharivorus  and  Togo hemipterus;    
     (d) pests of the family Miridae such as Halticus  insularis, Lygus lineolaris, Psuedatomoscelis seriatus, Stenodema sibiricum, Stenotus rubrovittatus  and  Trigonotylus caelestialium;    
     (e) pests of the family Pentatomidae, for example, species belonging to the genus  Nezara  ( Nezara  spp.) such as  Nezara antennata  and  Nezara viridula ; for example, species belonging to the genus  Eysarcoris  ( Eysarcoris  spp.) such as  Eysarcoris aeneus, Eysarcoris lewisi  and  Eysarcoris ventralis ; and others such as  Dolycoris baccarum, Eurydema rugosum, Glaucias subpunctatus, Halyomorpha halys, Piezodorus hybneri, Plautia crossota  and  Scotinophora lurida;    
     (f) pests of the family Pyrrhocoridae such as  Dysdercus cingulatus;    
     (g) pests of the family Rhopalidae such as  Rhopalus msculatus;    
     (h) pests of the family Scutelleridae such as  Eurygaster integriceps ; and 
     (i) pests of the family Tingidae such as  Stephanitis nashi.    
     (D) Sternorrhyncha 
     (a) pests of the family Adelgidae such as  Adelges laricis;    
     (b) pests of the family Aleyrodidae, for example, species belonging to the genus  Bemisia  ( Bemisia  spp.) such as  Bemisia argentifolii  and  Bemisia tabaci ; and others such as  Aleurocanthus spiniferus, Dialeurodes citri  and  Trialeurodes vaporariorum;    
     (c) pests of the family Aphididae, for example, species belonging to the genus  Aphis  ( Aphis  spp.) such as  Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis gossypii, Aphis pomi, Aphis sambuci  and  Aphis spiraecola ; for example, species belonging to the genus  Rhopalosiphum  ( Rhopalosiphum  spp.) such as  Rhopalosiphum maidis  and  Rhopalosiphum padi ; for example, species belonging to the genus  Dysaphis  ( Dysaphis  spp.) such as  Dysaphis plantaginea  and  Dysaphis radicola ; for example, species belonging to the genus  Macrosiphum  ( Macrosiphum  spp.) such as  Macrosiphum avenae  and  Macrosiphum euphorbiae ; for example, species belonging to the genus  Myzus  ( Myzus  spp.) such as  Myzus cerasi, Myzus persicae  and  Myzus varians ; and others such as  Acyrthosiphon pisum, Aulacorthum solani, Brachycaudus helichrysi, Brevicoryne brassicae, Chaetosiphon fragaefolii, Hyalopterus pruni, Hyperomyzus lactucae, Lipaphis erysimi, Megoura viciae, Metopolophium dirhodum, Nasonovia ribis - nigri, Phorodon humuli, Schizaphis graminum, Sitobion avenae  and  Toxoptera aurantii;    
     (d) pests of the family Coccidae, for example, species belonging to the genus  Ceroplastes  ( Ceroplastes  spp.) such as  Ceroplastes ceriferus  and  Ceroplastes rubens;    
     (e) pests of the family Diaspididae, for example, species belonging to the genus  Pseudaulacaspis  ( Pseudaulacaspis  spp.) such as  Pseudaulacaspis pentagona  and  Pseudaulacaspis prunicola ; for example, species belonging to the genus  Unaspis  ( Unaspis  spp.) such as  Unaspis euonymi  and  Unaspis yanonensis ; and others such as  Aonidiella aurantii, Comstockaspis perniciosa, Fiorinia theae  and  Pseudaonidia paeoniae;    
     (f) pests of the family Margarodidae such as  Drosicha corpulenta  and  Icerya purchasi;    
     (g) pests of the family Phylloxeridae such as  Viteus vitifolii;    
     (h) pests of the family Pseudococcidae, for example, species belonging to the genus  Planococcus  ( Planococcus  spp.) such as  Planococcus citri  and  Planococcus kuraunhiae ; and others such as  Phenacoccus solani  and  Pseudococcus comstocki ; and 
     (i) pests of the family Psyllidae, for example, species belonging to the genus  Psylla  ( Psylla  spp.) such as  Psylla mali  and  Psylla pyrisuga ; and others such as  Diaphorina citri.    
     (4) Insect Pests of the Suborder Polyphaga 
     (a) pests of the family Anobiidae such as  Lasioderma serricorne;    
     (b) pests of the family Attelabidae such as  Byctiscus betulae  and  Rhynchites heros;    
     (c) pests of the family Bostrichidae such as  Lyctus brunneus;    
     (d) pests of the family Brentidae such as  Cylas formicarius;    
     (e) pests of the family Buprestidae such as  Agrilus sinuatus;    
     (f) pests of the family Cerambycidae such as  Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris and Xylotrechus pyrrhoderus;    
     (g) pests of the family Chrysomelidae, for example, species belonging to the genus  Bruchus  ( Bruchus  spp.) such as  Bruchus pisorum  and  Bruchus rufimanus ; for example, species belonging to the genus  Diabrotica  ( Diabrotica  spp.) such as  Diabrotica barberi, Diabrotica  undecimpunctata and  Diabrotica virgifera ; for example, species belonging to the genus  Phyllotreta  ( Phyllotreta  spp.) such as  Phyllotreta nemorum  and  Phyllotreta striolata ; and others such as  Aulacophora femoralis, Callosobruchus chinensis, Cassida nebulosa, Chaetocnema concinna, Leptinotarsa decemlineata, Oulema oryzae  and  Psylliodes angusticollis;    
     (h) pests of the family Coccinellidae, for example, species belonging to the genus  Epilachna  ( Epilachna  spp.) such as  Epilachna varivestis  and  Epilachna vigintioctopunctata;    
     (i) pests of the family Curculionidae, for example, species belonging to the genus  Anthonomus  ( Anthonomus  spp.) such as  Anthonomus grandis  and  Anthonomus pomorum ; for example, species belonging to the genus  Sitophilus  ( Sitophilus  spp.) such as  Sitophilus granarius  and  Sitophilus zeamais ; and others such as  Echinoenemus squameus, Euscepes postfasciatus, Hylobius abietis, Hypera postica, Lissohoptrus oryzophilus, Otiorhynchus sulcatus, Sitona lineatus  and  Sphenophorus venatus;    
     (j) pests of the family Elateridae, for example, species belonging to the genus  Melanotus  ( Melanotus  spp.) such as  Melanotus fortnumi  and  Melanotus tamsuyensis;    
     (k) pests of the family Nitidulidae such as  Epuraea domina;    
     (l) pests of the family Scarabaeidae, for example, species belonging to the genus  Anomala  ( Anomala  spp.) such as  Anomala cuprea  and  Anomala rufocuprea ; and others such as  Cetonia aurata, Gametis jucunda, Heptophylla picea, Melolontha melolontha  and  Popillia japonica;    
     (m) pests of the family Scolytidae such as  Ips typographus;    
     (n) pests of the family Staphylinidae such as  Paederus fuscipes;    
     (o) pests of the family Tenebrionidae such as  Tenebrio molitor  and  Tribolium castaneum ; and 
     (p) pests of the family Trogossitidae such as  Tenebroides mauritanicus.    
     (5) Insect Pests of the Order Diptera 
     (A) Brachycera 
     (a) pests of the family Agromyzidae, for example, species belonging to the genus  Liriomyza  ( Liriomyza  spp.) such as  Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae  and  Liriomyza trifolii ; and others such as  Chromatomyia horticola  and  Agromyza oryzae;    
     (b) pests of the family Anthomyiidae, for example, species belonging to the genus  Delia  ( Delia  spp.) such as  Delia platura  and  Delia radicum ; and others such as  Pegomya cunicularia;    
     (c) pests of the family Drosophilidae, for example, species belonging to the genus  Drosophila  ( Drosophila  spp.) such as  Drosophila melanogaster  and  Drosophila  suzukii; 
     (d) pests of the family Ephydridae such as  Hydrellia griseola;    
     (e) pests of the family Psilidae such as  Psila rosae ; and 
     (f) pests of the family Tephritidae, for example, species belonging to the genus  Bactrocera  ( Bactrocera  spp.) such as  Bactrocera cucurbitae  and  Bactrocera dorsalis ; for example, species belonging to the genus  Rhagoletis  ( Rhagoletis  spp.) such as  Rhagoletis cerasi  and  Rhagoletis pomonella ; and others such as  Ceratitis capitata  and  Dacus oleae.    
     (B) Nematocera 
     (a) pests of the family Cecidomyiidae such as  Asphondylia yushimai, Contarinia sorghicola, Mayetiola destructor  and  Sitodiplosis mosellana.    
     (6) Insect Pests of the Order Orthoptera 
     (a) pests of the family Acrididae, for example, species belonging to the genus  Schistocerca  ( Schistocerca  spp.) such as  Schistocerca americana  and  Schistocerca gregaria ; and others such as  Chortoicetes terminifera, Dociostaurus maroccanus, Locusta migratoria, Locustana pardalina, Nomadacris septemfasciata  and  Oxya yezoensis;    
     (b) pests of the family Gryllidae such as  Acheta domestica  and  Teleogryllus emma;    
     (c) pests of the family Gryllotalpidae such as  Gryllotalpa orientalis ; and 
     (d) pests of the family Tettigoniidae such as  Tachycines asynamorus.    
     (7) Acari 
     (A) Acaridida of the Order Astigmata 
     (a) mites and ticks of the family Acaridae, for example, species belonging to the genus  Rhizoglyphus  ( Rhizoglyphus  spp.) such as  Rhizoglyphus echinopus  and  Rhizoglyphus robini ; for example, species belonging to the genus  Tyrophagus  ( Tyrophagus  spp.) such as  Tyrophagus neiswanderi, Tyrophagus perniciosus, Tyrophagus putrescentiae  and  Tyrophagus similis ; and others such as  Acarus siro, Aleuroglyphus ovatus  and  Mycetoglyphus fungivorus;    
     (B) Actinedida of the Order Prostigmata 
     (a) mites and ticks of the family Tetranychidae, for example, species belonging to the genus  Bryobia  ( Bryobia  spp.) such as  Bryobia praetiosa  and  Bryobia rubrioculus ; for example, species belonging to the genus  Eotetranychus  ( Eotetranychus  spp.) such as  Eotetranychus asiaticus, Eotetranychus boreus, Eotetranychus celtis, Eotetranychus geniculatus, Eotetranychus kankitus, Eotetranychus pruni, Eotetranychus shii, Eotetranychus smithi, Eotetranychus suginamensis  and  Eotetranychus uncatus ; for example, species belonging to the genus  Oligonychus  ( Oligonychus  spp.) such as  Oligonychus hondoensis, Oligonychus ilicis, Oligonychus karamatus, Oligonychus mangiferus, Oligonychus orthius, Oligonychus perseae, Oligonychus pustulosus, Oligonychus shinkajii  and  Oligonychus ununguis ; for example, species belonging to the genus  Panonychus  ( Panonychus  spp.) such as  Panonychus citri, Panonychus mori  and  Panonychus ulmi ; for example, species belonging to the genus  Tetranychus  ( Tetranychus  spp.) such as  Tetranychus cinnabarinus, Tetranychus evansi, Tetranychus kanzawai, Tetranychus ludeni, Tetranychus quercivorus, Tetranychus phaselus, Tetranychus urticae  and  Tetranychus viennensis ; for example, species belonging to the genus  Aponychus  ( Aponychus  spp.) such as  Aponychus corpuzae  and  Aponychus firmianae ; for example, species belonging to the genus  Sasanychus  ( Sasanychus  spp.) such as  Sasanychus akitanus  and  Sasanychus pusillus ; for example, species belonging to the genus  Shizotetranychus  ( Shizotetranychus  spp.) such as  Shizotetranychus celarius, Shizotetranychus longus, Shizotetranychus miscanthi, Shizotetranychus recki  and  Shizotetranychus schizopus ; and others such as  Tetranychina harti, Tuckerella pavoniformis  and  Yezonychus sapporensis;    
     (b) mites and ticks of the family Tenuipalpidae, for example, species belonging to the genus  Brevipalpus  ( Brevipalpus  spp.) such as  Brevipalpus lewisi, Brevipalpus obovatus, Brevipalpus phoenicis, Brevipalpus russulus  and  Brevipalpus californicus ; for example, species belonging to the genus  Tenuipalpus  ( Tenuipalpus  spp.) such as  Tenuipalpus pacificus  and  Tenuipalpus zhizhilashviliae ; and others such as  Dolichotetranychus floridanus;    
     (c) mites and ticks of the family Eriophyidae, for example, species belonging to the genus  Aceria  ( Aceria  spp.) such as  Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, Aceria paradianthi, Aceria tiyingi, Aceria tulipae  and  Aceria zoysiea ; for example, species belonging to the genus  Eriophyes  ( Eriophyes  spp.) such as  Eriophyes chibaensis  and  Eriophyes emarginatae ; for example, species belonging to the genus  Aculops  ( Aculops  spp.) such as  Aculops lycopersici  and  Aculops pelekassi ; for example, species belonging to the genus  Aculus  ( Aculus  spp.) such as  Aculus fockeui  and  Aculus schlechtendali ; and others such as  Acaphylla theavagrans, Calacarus carinatus, Colomerus vitis, Calepitrimerus vitis, Epitrimerus pyri, Paraphytoptus kikus, Paracalacarus podocarpi  and  Phyllocotruta citri;    
     (d) mites and ticks of the family Transonemidae, for example, species belonging to the genus  Tarsonemus  ( Tarsonemus  spp.) such as  Tarsonemus bilobatus  and  Tarsonemus waitei ; and others such as  Phytonemus pallidus  and  Polyphagotarsonemus latus ; and 
     (e) mites and ticks of the family Penthaleidae, for example, species belonging to the genus  Penthaleus  ( Penthaleus  spp.) such as  Penthaleus erythrocephalus  and  Penthaleus major.    
     The pest control agent of the present invention may be mixed with or used in combination with other active ingredients such as fungicides, insecticidal and acaricidal agents, nematicides and soil pesticides; plant regulators, synergists, fertilizers, soil conditioners, animal feeds and the like. 
     A combination of the compound of the present invention and other active ingredients can be expected to have a synergistic effect on insecticidal, acaricidal and nematicidal activities. The synergistic effect can be confirmed by the Colby&#39;s formula (Colby, S. R.; Calculating Synergistic and Antagonistic Responses of Herbicide Combinations; Weeds 15, pp. 20-22, 1967) according to a conventional method. 
     Specific examples of insecticidal/acaricidal agents, nematicides, soil pesticides, anthelmintics and the like which can be mixed with or used in combination with the pest control agent of the present invention are shown below. 
     (1) Acetylcholinesterase inhibitors: 
     (a) carbamate-based inhibitors: alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb, fenothiocarb, MIPC, MPMC, MTMC, aldoxycarb, allyxycarb, aminocarb, bufencarb, cloethocarb, metam sodium, promecarb; 
     (b) Organophosphorus-based inhibitors: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isocarbophos, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimphos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion; bromophos-ethyl, BRP, carbophenothion, cyanofenphos, demeton-S-methyl sulfone, dialifos, dichlofenthion, dioxabenzofos, etrimfos, fensulfothion, flupyrazofos, fonofos, formothion, fosmethilan, isazofos, iodofenphos, methacrifos, pirimiphos-ethyl, phosphocarb, propaphos, prothoate, sulprofos. 
     (2) GABA-gated chloride channel antagonists: acetoprole, chlordane, endosulfan, ethiprole, fipronil, pyrafluprole, pyriprole; camphechlor, heptachlor, dienochlor. 
     (3) Sodium channel modulators: acrinathrin, d-cis/trans allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentyl isomers, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, ganma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans isomers], deltamethrin, empenthrin [(EZ)-(1R)-isomers], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin [(1R)-trans isomers], prallethrin, pyrethrum, resmethrin, silafluofen, tefluthrin, tetramethrin [(1R)-isomers], tralomethrin, transfluthrin, allethrin, pyrethrin, pyrethrin I, pyrethrin II, profluthrin, dimefluthrin, bioethanomethrin, biopermethrin, transpermethrin, fenfluthrin, fenpirithrin, flubrocythrinate, flufenprox, metofluthrin, protrifenbute, pyresmethrin, terallethrin. 
     (4) Nicotinic acetylcholine receptor agonists: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyradifurone, flupyrimin. 
     (5) Nicotinic acetylcholine receptor allosteric modulators: spinetoram, spinosad. 
     (6) Chloride channel activators: abamectin, emamectin benzoate, lepimectin, milbemectin; ivermectin, selamectin, doramectin, eprinomectin, moxidectin, milbemycin, milbemycin oxime, nemadectin. 
     (7) Juvenile hormone analogues: hydroprene, kinoprene, methoprene, fenoxycarb, pyriproxyfen, diofenolan, epofenonane, triprene. 
     (8) Other nonspecific inhibitors: methyl bromide, chloropicrin, sulfuryl fluoride, borax, tartar emetic. 
     (9) Homoptera selective antifeedants: flonicamid, pymetrozine, pyrifluquinazon. 
     (10) Mite growth inhibitors: clofentezine, diflovidazin, hexythiazox, etoxazole. 
     (11) Insect midgut inner membrane distrupting agents derived from microorganisms:  Bacillus thuringiensis  subsp.  israelensi, Bacillus sphaericus, Bacillus thuringiensis  subsp.  aizawai, Bacillus thuringiensis  subsp.  kurstaki, Bacillus thuringiensis  subsp.  tenebrionis , Bt crop proteins, Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/Cry35Ab1. 
     (12) Mitochondrial ATP biosynthetic enzyme inhibitors: diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon. 
     (13) Oxidative phosphorylation uncouplers: chlorfenapyr, sulfluramid, DNOC; binapacryl, dinobuton, dinocap. 
     (14) Nicotinic acetylcholine receptor channel blockers: bensultap, cartap hydrochloride, nereistoxin, thiosultap-sodium salt, thiocyclam. 
     (15) Chitin synthesis inhibitors: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, buprofezin, fluazuron. 
     (16) Diptera molting disrupting agents: cyromazine. 
     (17) Molting hormone 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, tolfenpyrad, rotenone. 
     (21) Voltage-dependent sodium channel blockers: indoxacarb, metaflumizone. 
     (22) Acetyl CoA carboxylase inhibitors: spirodiclofen, spiromesifen, spirotetramat, 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, tetraniliprole. 
     (26) Mixed function oxidase inhibitor compounds: piperonyl butoxide. 
     (27) Latrophilin receptor agonists: depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside. 
     (28) Other agents (with unknown action mechanisms): acynonapyr, azadirachtin, benzoximate, bromopropylate, chinomethionate, cryolite, dicofol, pyridalyl, benclothiaz, sulfur, amidoflumet, 1,3-dichloropropene, DCIP, phenisobromolate, benzomate, metaldehyde, chlorobenzilate, clothiazoben, dicyclanil, fenoxacrim, fentrifanil, flubenzimine, fluphenazine, gossyplure, japonilure, metoxadiazone, petroleum, sodium oleate, tetrasul, triarathene, afidopyropen, flometoquin, flufiprole, fluensulfone, meperfluthrin, tetramethylfluthrin, tralopyril, 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), broflanilide, triflumezopyrim, dicloromezotiaz, oxazosulfyl, other meta-diamides, tyclopyrazoflor. 
     (29) Anthelmintics: 
     (a) benzimidazole-based anthelmintics: fenbendazole, albendazole, triclabendazole, oxibendazole, mebendazole, oxfendazole, parbendazole, flubendazole; febantel, netobimin, thiophanate; thiabendazole, cambendazole; 
     (b) salicylanilide-based anthelmintics: closantel, oxyclozanide, rafoxanide, niclosamide; 
     (c) substituted phenol-based anthelmintics: nitroxinil, nitroscanate; 
     (d) pyrimidine-based anthelmintics: pyrantel, morantel; 
     (e) imidazothiazole-based anthelmintics: levamisole, tetramisole; 
     (f) tetrahydropyrimidine-based anthelmintics: praziquantel, epsiprantel; and 
     (g) other anthelmintics: cyclodien, ryania, clorsulon, metronidazole, demiditraz; piperazine, diethylcarbamazine, dichlorophen, monepantel, tribendimidine, amidantel; thiacetarsamide, melorsamine, arsenamide. 
     Specific examples of the fungicide which can be mixed with or used in combination with the pest control agent of the present invention are shown below. 
     (1) Nucleic Acid Biosynthesis Inhibitors: 
     (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 inhibitors: oxolinic acid. 
     (2) Mitotic Inhibitors and Cell Division Inhibitors: 
     (a) β-tubulin polymerization inhibitors: benomyl, carbendazim, chlorfenazole, fuberidazole, thiabendazole, thiophanate, thiophanate methyl, diethofencarb, zoxamide, ethaboxam; 
     (b) cell division inhibitors: pencycuron; 
     (c) delocalization inhibitors of spectrin-like protein: fluopicolide. 
     (3) Respiratory Inhibitors: 
     (a) complex I NADH oxidoreductase inhibitors: diflumetorim, tolfenpyrad; 
     (b) complex II succinate dehydrogenase inhibitors: benodanil, flutolanil, mepronil, isofetamid, fluopyram, fenfuram, furmecyclox, carboxin, oxycarboxin, thifluzamide, benzovindiflupyr, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, boscalid, pyrapropoyne; 
     (c) complex III ubiquinol oxidase Qo inhibitors: azoxystrobin, coumoxystrobin, coumethoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin, pyraclostrobin, pyrametostrobin, triclopyricarb, kresoxim-methyl, trifloxystrobin, dimoxystrobin, fenaminstrobin, metominostrobin, orysastrobin, famoxadone, fluoxastrobin, fenamidone, pyribencarb; 
     (d) complex III ubiquinol reductase Qi inhibitors: cyazofamid, amisulbrom; 
     (e) oxidative phosphorylation uncouplers: binapacryl, meptyldinocap, dinocap, fluazinam, ferimzone; 
     (f) oxidative phosphorylation inhibitors (ATP synthase inhibitors): fentin acetate, fentin chloride, fentin hydroxide; 
     (g) ATP production inhibitor: silthiofam; 
     (h) complex III: Qx (unknown) inhibitor of cytochrome bc1 (ubiquinone reductase): ametoctradin. 
     (4) Amino Acid and Protein Synthesis Inhibitors 
     (a) methionine biosynthesis inhibitors: andoprim, cyprodinil, mepanipyrim, pyrimethanil; 
     (b) protein synthesis inhibitors: blasticidin S, kasugamycin, kasugamycin hydrochloride, streptomycin, oxytetracycline. 
     (5) Signal Transduction Inhibitors: 
     (a) Signal transduction inhibitors: quinoxyfen, proquinazid; 
     (b) MAP/histidine kinase inhibitors in osmotic signal transduction: fenpiclonil, fludioxonil, chlozolinate, iprodione, procymidone, vinclozolin. 
     (6) Lipid and Cell Membrane Synthesis Inhibitors: 
     (a) phospholipid biosynthesis and methyltransferase inhibitors: edifenphos, iprobenfos, pyrazophos, isoprothiolane; 
     (b) lipid peroxidation agents: biphenyl, chloroneb, dicloran, quintozene, teenazene, tolclofos-methyl, etridiazole; 
     (c) agents acting on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb-fosetylate, prothiocarb; 
     (d) microorganisms disturbing pathogenic cell membranes:  Bacillus subtilis, Bacillus subtilis  strain QST713,  Bacillus subtilis  strain FZB24,  Bacillus subtilis  strain MBI600,  Bacillus subtilis  strain D747; 
     (e) agents disturbing cell membranes: extracts of  Melaleuca alternifolia  (tea tree). 
     (7) Sterol Biosynthesis Inhibitors of Cell Membranes: 
     (a) C14 demethylation inhibitors in sterol biosynthesis: triforine, pyrifenox, pyrisoxazole, fenarimol, flurprimidol, nuarimol; imazalil, imazalil sulfate, oxpoconazole, pefurazoate, prochloraz, triflumizole, viniconazole, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazol, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, fluconazole, furconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, fluquinconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, voriconazole; 
     (b) inhibitors of Δ14 reductase and Δ8→Δ7-isomerase in sterol biosynthesis: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidine, piperalin, spiroxamine; 
     (c) 3-keto reductase inhibitors in C4 demethylation in sterol biosynthesis system: fenhexamid, fenpyrazamine; 
     (d) squalene epoxidase inhibitors in sterol biosynthesis system: pyributicarb; naftifine, terbinafine. 
     (8) Cell wall synthesis inhibitors 
     (a) trehalase inhibitor: validamycin; 
     (b) chitin synthase inhibitors: polyoxins, polyoxorim; 
     (c) cellulose synthase inhibitors: dimethomorph, flumorph, pyrimorph, benthiavalicarb, iprovalicarb, tolprocarb, valifenalate, mandipropamid. 
     (9) Melanin biosynthesis inhibitors 
     (a) reductase inhibitors in melanin biosynthesis: fthalide, pyroquilon, tricyclazole; 
     (b) anhydrase inhibitors in melanin biosynthesis: carpropamid, diclocymet, fenoxanil; 
     (10) Resistance inducers of host plants: 
     (a) agent acting on salicylic acid synthetic pathway: acibenzolar-S-methyl; 
     (b) other agents: probenazole; tiadinil; isotianil; laminarin;  Reynoutria sachalinensis  extract. 
     (11) agents with unknown actions: cymoxanil, fosetyl-aluminium, phosphoric acid (phosphates), tecloftalam, triazoxide, flusulfamide, diclomezine, methasulfocarb, cyflufenamid, metrafenone, pyriofenone, dodine, dodine free base, flutianil. 
     (12) agents having multiple points of action: copper (copper salts), Bordeaux mixture, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; ferbam, mancozeb, maneb, mancopper, metiram, polycarbamate, propineb, thiram, zineb, ziram, captan, captafol, folpet, chlorothalonil, dichlofluanid, tolylfluanid, guazatine, iminoctadine acetates (iminoctadine triacetate), iminoctadine albesilates (iminoctadine trialbesilate), anilazine, dithianon, chinomethionate, fluoroimide. 
     (13) Other agents: DBEDC, fluorofolpet, guazatine acetate, bis(8-quinolinolato)copper(II), propamidine, chloropicrin, cyprofuram, agrobacterium, bethoxazin, diphenylamine, methyl isothiocyanate (MITC), mildiomycin, capsaicin, cufraneb, cyprosulfamide, dazomet, debacarb, dichlorophen, difenzoquat, difenzoquat methyl sulfate, flumetover, fosetyl calcium, fosetyl sodium, irumamycin, natamycin, nitrothal-isopropyl, oxamocarb, propanosine-sodium, pyrrolnitrin, tebufloquin, tolnifanide, zarilamid, algophase, amicarthiazol, oxathiapiprolin, metiram zinc, benthiazole, trichlamide, uniconazole, mildiomycin, oxyfenthiin, picarbutrazox. 
     Specific examples of plant regulators which can be mixed with or used in combination with the pest control agent of the present invention are shown below. 1-Methylcyclopropene, 2,3,5-triiodobenzoic acid, IAA, IBA, MCPA, MCPB, 4-CPA, 5-aminolevulinic acid hydrochloride, 6-benzylaminopurine, abscisic acid, aviglycine hydrochloride, ancymidol, butralin, calcium carbonate, calcium chloride, calcium formate, calcium peroxide, lime sulfur, calcium sulfate, chlormequat chloride, chlorpropham, choline chloride, cloprop, cyanamide, cyclanilide, daminozide, decyl alcohol, dichlorprop, dikegulac, dimethipin, diquat, ethephon, ethychlozate, flumetralin, flurprimidol, forchlorfenuron, gibberellin A, gibberellin A3, hymexazol, inabenfide, isoprothiolane, kinetin, maleic hydrazide, mefluidide, mepiquat chloride, oxidized glutathione, paclobutrazol, pendimethalin, prohexadione calcium, prohydrojasmon, pyraflufen-ethyl, sintofen, sodium 1-naphthaleneacetate, sodium cyanate, streptomycin, thidiazuron, triapenthenol, tribufos, trinexapac-ethyl, uniconazole P, and 1-naphthylacetamide. 
     [Ectoparasite Control Agent] 
     The ectoparasite control agent of the present invention contains at least one selected from the pyridinium salts of the present invention as an active ingredient. The amount of the compound of the present invention contained in the ectoparasite control agent of the present invention is not particularly limited as long as it shows the effect of controlling ectoparasites, but it is usually preferably within the range of 0.01 to 95 parts by mass with respect to 100 parts by mass of the control agent of the present invention. 
     Examples of host animals to be treated with the ectoparasite control agent of the present invention include warm-blooded animals including pet animals such as dogs and cats; pet birds; domestic animals such as cattle, horses, pigs and sheep; domestic fowls; and the like. In addition, honey bees, stag beetles and beetles can be exemplified. 
     The ectoparasite control agent of the present invention can be applied by a known veterinary method (topical, oral, parenteral or subcutaneous administration). As a method therefor, a method of orally administering tablets, capsules, mixed feeds or the like to the animals; a method of administering to the animals by using an immersion liquid, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal or the like) or the like; a method of topically administering by spraying, pouring-on or spotting-on an oily or aqueous liquid preparation; a method of kneading an ectoparasite control agent in a resin, molding the kneaded product into an appropriate shape such as a collar, ear tag or the like, and attaching and topically administering the resultant to the animals; and the like can be mentioned. 
     Ectoparasites are parasitic in and on host animals, especially warm-blooded animals. More specifically, the ectoparasites are parasitic in and on the back, armpit, lower abdomen, inner thigh and the like of the host animals and obtain nutritional sources such as blood and dandruff from the animals to live. Examples of ectoparasites include mites and ticks, lice, fleas, mosquitoes, stable flies, flesh flies and the like. Specific examples of the ectoparasites which can be controlled by the ectoparasite control agent of the present invention are shown below. 
     (1) Acari 
     Mites and ticks belonging to the family Dermanyssidae, mites and ticks belonging to the family Macronyssidae, mites and ticks belonging to the family Laelapidae, mites and ticks belonging to the family Varroidae, mites and ticks belonging to the family Argasidae, mites and ticks belonging to the family Ixodidae, mites and ticks belonging to the family Psoroptidae, mites and ticks belonging to the family Sarcoptidae, mites and ticks belonging to the family Knemidokoptidae, mites and ticks belonging to the family Demodixidae, mites and ticks belonging to the family Trombiculidae, insect-parasitic mites and ticks such as  Coleopterophagus berlesei  or the like. 
     (2) Phthiraptera 
     Lice belonging to the family Haematopinidae, lice belonging to the family Linognathidae, biting lice belonging to the family Menoponidae, biting lice belonging to the family Philopteridae, biting lice belonging to the family Trichodectidae. 
     (3) Siphonaptera 
     Fleas of the family Pulicidae, for example, species belonging to the genus  Ctenocephalides  ( Ctenocephalides  spp.) such as  Ctenocephalides canis  and  Ctenocephalides felis;    
     fleas belonging to the family Tungidae, fleas belonging to the family Ceratophyllidae, fleas belonging to the family Leptopsyllidae. 
     (4) Hemiptera 
     (5) Insect Pests of the Order Diptera 
     Mosquitoes belonging to the family Culicidae, black flies belonging to the family Simuliidae, biting midges belonging to the family Ceratopogonidae, horseflies belonging to the family Tabanidae, flies belonging to the family Muscidae, tsetse flies belonging to the family Glossinidae; flesh flies belonging to the family Sarcophagidae, flies belonging to the family Hippoboscidae, flies belonging to the family Calliphoridae, flies belonging to the family Oestridae. 
     [Endoparasite Control- or Exterminating Agent] 
     The endoparasite control- or exterminating agent of the present invention contains at least one selected from the pyridinium salts of the present invention as an active ingredient. The amount of the compound of the present invention contained in the endoparasite control- or exterminating agent of the present invention is not particularly limited as long as it shows the effect of controlling endoparasites, but it is usually preferably within the range of 0.01 to 95 parts by mass with respect to 100 parts by mass of the control- or exterminating agent of the present invention. 
     The parasite to be targeted by the endoparasite control- or exterminating agent of the present invention is parasitic (endoparasitic) in host animals, especially warm blooded animals and fish. Examples of host animals for which the endoparasite control- or exterminating agent of the present invention is effective include warm-blooded animals such as humans, domestic mammals (for example, cattle, horses, pigs, sheep, goats and the like), laboratory animals (for example, mice, rats, gerbils and the like), pet animals (for example, hamsters, guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, and the like), wild and zoo mammals (monkeys, foxes, deers, buffaloes and the like), domestic fowls (turkeys, ducks, chickens, quails, geese and the like) and pet birds (pigeons, parrots, hill mynas, Java sparrows, parakeets, society finches, canaries and the like); or fish such as salmon, trout and nishikigoi. By controlling and exterminating parasites, it is possible to prevent or treat parasitic diseases mediated by the parasites. 
     Examples of the parasites to be controlled or exterminated include the followings. 
     (1) Nematodes of the Order Dioctophymatida 
     (a) kidney worms of the family Dioctophymatidae, for example, species belonging to the genus  Dioctophyma  ( Dioctophyma  spp.) such as  Dioctophyma renale ; and 
     (b) kidney worms of the family Soboliphymatidae, for example, species belonging to the genus  Soboliphyme  ( Soboliphyme  spp.) such as  Soboliphyme abei  and  Soboliphyme baturini.    
     (2) Nematodes of the Order Trichocephalida 
     (a) trichina worms of the family Trichinellidae, for example, species belonging to the genus  Trichinella  ( Trichinella  spp.) such as  Trichinella spiralis ; and 
     (b) whipworms of the family Trichuridae, for example, species belonging to the genus  Capillaria  ( Capillaria  spp.) such as  Capillaria annulata, Capillaria contorta, Capillaria hepatica, Capillaria perforans, Capillaria plica , and  Capillaria suis ; and species belonging to the genus  Trichuris  ( Trichuris  spp.) such as  Trichuris vulpis, Trichuris discolor, Trichuris ovis, Trichuris skrjabini , and  Trichuris suis.    
     (3) Nematodes of the Order Rhabditida 
     threadworms of the family Strongyloididae, for example, species belonging to the genus  Strongyloides  ( Strongyloides  spp.) such as  Strongyloides papillosus, Strongyloides planiceps, Strongyloides ransomi, Strongyloides suis, Strongyloides stercoralis, Strongyloides tumefaciens , and  Strongyloides ratti.    
     (4) Nematodes of the Order Strongylida 
     hookworms of the family Ancylostomatidae, for example, species belonging to the genus  Ancylostoma  ( Ancylostoma  spp.) such as  Ancylostoma braziliense, Ancylostoma caninum, Ancylostoma duodenale , and  Ancylostoma tubaeforme ; species belonging to the genus  Uncinaria  ( Uncinaria  spp.) such as  Uncinaria stenocephala ; and species belonging to the genus  Bunostomum  ( Bunostomum  spp.) such as  Bunostomum phlebotomum  and  Bunostomum trigonocephalum.    
     (5) Nematodes of the Order Strongylida 
     (a) nematodes of the family Angiostrongylidae, for example, species belonging to the genus  Aelurostrongylus  ( Aelurostrongylus  spp.) such as  Aelurostrongylus abstrusus ; and species belonging to the genus  Angiostrongylus  ( Angiostrongylus  spp.) such as  Angiostrongylus vasorum  and  Angiostrongylus cantonesis;    
     (b) nematodes of the family Crenosomatidae, for example, species belonging to the genus  Crenosoma  ( Crenosoma  spp.) such as  Crenosoma aerophila  and  Crenosoma vulpis;    
     (c) nematodes of the family Filaroididae, for example, species belonging to the genus  Filaroides  ( Filaroides  spp.) such as  Filaroides hirthi  and  Filaroides osleri;    
     (d) lungworms of the family Metastrongylidae, for example, species belonging to the genus  Metastrongylus  ( Metastrongylus  spp.) such as  Metastrongylus apri, Metastrongylus asymmetricus, Metastrongylus pudendotectus  and  Metastrongylus salmi; and    
     (e) gapeworms of the family Syngamidae, for example, species belonging to the genus  Cyathostoma  ( Cyathostoma  spp.) such as  Cyathostoma bronchialis ; and species belonging to the genus  Syngamus  ( Syngamus  spp.) such as  Syngamus skrjabinomorpha  and  Syngamus trachea.    
     (6) Nematodes of the Order Strongylida 
     (a) nematodes of the family Molineidae, for example, species belonging to the genus  Nematodirus  ( Nematodirus  spp.) such as  Nematodirus filicollis  and  Nematodirus spathiger;    
     (b) nematodes of the family Dictyocaulidae, for example, species belonging to the genus  Dictyocaulus  ( Dictyocaulus  spp.) such as  Dictyocaulus filaria  and  Dictyocaulus viviparus;    
     (c) nematodes of the family Haemonchidae, for example, species belonging to the genus  Haemonchus  ( Haemonchus  spp.) such as  Haemonchus contortus ; and species belonging to the genus  Mecistocirrus  ( Mecistocirrus  spp.) such as  Mecistocirrus digitatus;    
     (d) nematodes of the family Haemonchidae, for example, species belonging to the genus  Ostertagia  ( Ostertagia  spp.) such as  Ostertagia ostertagi;    
     (e) nematodes of the family Heligmonellidae, for example, species belonging to the genus  Nippostrongylus  ( Nippostrongylus  spp.) such as  Nippostrongylus braziliensis ; and 
     (f) nematodes of the family Trichostrongylidae, for example, species belonging to the genus  Trichostrongylus  ( Trichostrongylus  spp.) such as  Trichostrongylus axei, Trichostrongylus colubriformis  and  Trichostrongylus tenuis ; species belonging to the genus  Hyostrongylus  ( Hyostrongylus  spp.) such as  Hyostrongylus rubidus ; and species belonging to the genus  Obeliscoides  ( Obeliscoides  spp.) such as  Obeliscoides cuniculi.    
     (7) Nematodes of the Order Strongylida 
     (a) nematodes of the family Chabertiidae, for example, species belonging to the genus  Chabertia  ( Chabertia  spp.) such as  Chabertia ovina ; and species belonging to the genus  Oesophagostomum  ( Oesophagostomum  spp.) such as  Oesophagostomum brevicaudatum, Oesophagostomum columbianum, Oesophagostomum dentatum, Oesophagostomum georgianum, Oesophagostomum maplestonei, Oesophagostomum quadrispinulatum, Oesophagostomum radiatum, Oesophagostomum venulosum  and  Oesophagostomum watanabei;    
     (b) nematodes of the family Stephanuridae, for example, species belonging to the genus  Stephanurus  ( Stephanurus  spp.) such as  Stephanurus dentatus ; and 
     (c) nematodes of the family Strongylidae, for example, species belonging to the genus  Strongylus  ( Strongylus  spp.) such as  Strongylus asini, Strongylus edentatus, Strongylus equinus  and  Strongylus vulgaris.    
     (8) Nematodes of the Order Oxyurida 
     nematodes of the family Oxyuridae, for example, species belonging to the genus  Enterobius  ( Enterobius  spp.) such as  Enterobius anthropopitheci  and  Enterobius vermicularis ; species belonging to the genus  Oxyuris  ( Oxyuris  spp.) such as  Oxyuris equi ; and species belonging to the genus  Passalurus  ( Passalurus  spp.) such as  Passalurus ambiguus.    
     (9) Nematodes of the Order Ascaridida 
     (a) nematodes of the family Ascaridiidae, for example, species belonging to the genus  Ascaridia  ( Ascaridia  spp.) such as  Ascaridia galli;    
     (b) nematodes of the family Heterakidae, for example, species belonging to the genus  Heterakis  ( Heterakis  spp.) such as  Heterakis beramporia, Heterakis brevispiculum, Heterakis gallinarum, Heterakis pusilla  and  Heterakis putaustralis;    
     (c) nematodes of the family Anisakidae, for example, species belonging to the genus  Anisakis  ( Anisakis  spp.) such as  Anisakis simplex;    
     (d) nematodes of the family Ascarididae, for example, species belonging to the genus  Ascaris  ( Ascaris  spp.) such as  Ascaris lumbricoides  and  Ascaris suum ; and species belonging to the genus  Parascaris  ( Parascaris  spp.) such as  Parascaris equorum ; and 
     (e) nematodes of the family Toxocaridae, for example, species belonging to the genus  Toxocara  ( Toxocara  spp.) such as  Toxocara canis, Toxocara leonina, Toxocara suum, Toxocara vitulorum  and  Toxocara cati.    
     (10) Nematodes of the Order Spirurida 
     (a) nematodes of the family Onchocercidae, for example, species belonging to the genus  Brugia  ( Brugia  spp.) such as  Brugia malayi, Brugia pahangi  and  Brugia patei ; species belonging to the genus  Dipetalonema  ( Dipetalonema  spp.) such as  Dipetalonema reconditum ; species belonging to the genus  Dirofilaria  ( Dirofilaria  spp.) such as  Dirofilaria immitis ; species belonging to the genus  Filaria  ( Filaria  spp.) such as  Filaria oculi ; and species belonging to the genus  Onchocerca  ( Onchocerca  spp.) such as  Onchocerca cervicalis, Onchocerca gibsoni  and  Onchocerca gutturosa;    
     (b) nematodes of the family Setariidae, for example, species belonging to the genus  Setaria  ( Setaria  spp.) such as  Setaria digitata, Setaria equina, Setaria labiatopapillosa  and  Setaria marshalli ; and species belonging to the genus  Wuchereria  ( Wuchereria  spp.) such as  Wuchereria bancrofti ; and 
     (c) nematodes of the family Filariidae, for example, species belonging to the genus  Parafilaria  ( Parafilaria  spp.) such as  Parafilaria multipapillosa ; and species belonging to the genus  Stephanofilaria  ( Stephanofilaria  spp.) such as  Stephanofilaria assamensis, Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria okinawaensis and Stephanofilaria stilesi.    
     (11) Nematodes of the Order Spirurida 
     (a) nematodes of the family Gnathostomatidae, for example, species belonging to the genus  Gnathostoma  ( Gnathostoma  spp.) such as  Gnathostoma doloresi  and  Gnathostoma spinigerum;    
     (b) nematodes of the family Habronematidae, for example, species belonging to the genus  Habronema  ( Habronema  spp.) such as  Habronema majus, Habronema microstoma  and  Habronema muscae ; and species belonging to the genus  Draschia  ( Draschia  spp.) such as  Draschia megastoma;    
     (c) nematodes of the family Physalopteridae, for example, species belonging to the genus  Physaloptera  ( Physaloptera  spp.) such as  Physaloptera canis, Physaloptera cesticillata, Physaloptera erdocyona, Physaloptera felidis, Physaloptera gemina, Physaloptera papilloradiata, Physaloptera praeputialis, Physaloptera pseudopraerutialis, Physaloptera rara, Physaloptera sibirica  and  Physaloptera vulpineus;    
     (d) nematodes of the family Gongylonematidae, for example, species belonging to the genus  Gongylonema  ( Gongylonema  spp.) such as  Gongylonema pulchrum;    
     (e) nematodes of the family Spirocercidae, for example, species belonging to the genus  Ascarops  ( Ascarops  spp.) such as  Ascarops strongylina ; and 
     (f) nematodes of the family Thelaziidae, for example, species belonging to the genus  Thelazia  ( Thelazia  spp.) such as  Thelazia callipaeda, Thelazia gulosa, Thelazia lacrymalis, Thelazia rhodesi  and  Thelazia skrjabini.    
     [Control Agents for Other Pests] 
     In addition, the compound of the present invention is excellent in the effect of controlling insect pests having a stinger or venom which harm humans and animals, insect pests that mediate various pathogens/pathogenic microbes, and insect pests that cause discomfort to humans (such as toxic pests, hygiene pests and unpleasant pests). 
     Specific examples thereof are shown below. 
     (1) Insect Pests of the Order Hymenoptera 
     Bees belonging to the family Argidae, bees belonging to the family Cynipidae, bees belonging to the family Diprionidae, ants belonging to the family Formicidae, bees belonging to the family Mutillidae, bees belonging to the family Vespidae. 
     (2) Other Pests 
     Cockroaches (Blattodea), termites, spiders (Araneae), centipedes, millipedes, crustaceans, bedbugs ( Cimex lectularius ). 
     EXAMPLES 
     [Pharmaceutical Formulation] 
     Although some pharmaceutical formulations of the pest control agent, insecticidal or acaricidal agent, ectoparasite control agent, or endoparasite control- or exterminating agent of the present invention are shown, additives and the addition ratios should not be limited to these examples and can be modified over a wide range. The term “part” in the formulations indicates “part by weight”. 
     The formulations for agricultural and horticultural use and for paddy rice are shown below. 
     (Formulation 1: Wettable Powder) 
     40 parts of the compound of the present invention, 53 parts of diatomaceous earth, 4 parts of a higher alcohol sulfuric acid ester and 3 parts of an alkyl naphthalene sulfonate are uniformly mixed and finely pulverized to obtain a wettable powder containing 40% of an 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 a polyoxyethylene alkyl allyl ether are mixed and dissolved to obtain an emulsion containing 30% of an active ingredient. 
     (Formulation 3: Granule) 
     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 a sodium alkylsulfate are uniformly mixed and finely pulverized, and then granulated into a granular form having a diameter of 0.5 to 1.0 mm to obtain a granule containing 5% of an active ingredient. 
     (Formulation 4: Granule) 
     5 parts of the compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of sodium dioctyl sulfosuccinate and 1 part of potassium phosphate are thoroughly ground and mixed, water is added and thoroughly kneaded, followed by granulation and drying to obtain a granule containing 5% of an active ingredient. 
     (Formulation 5: Suspension) 
     10 parts of the compound of the present invention, 4 parts of a polyoxyethylene alkyl allyl ether, 2 parts of a polycarboxylic acid sodium salt, 10 parts of glycerin, 0.2 parts of xanthan gum and 73.8 parts of water are mixed and subjected to wet grinding until the particle size becomes 3 microns or less to obtain a suspension containing 10% of an active ingredient. 
     The formulations of an ectoparasite control agent or an endoparasite control- or exterminating agent are shown below. 
     (Formulation 6: Granule) 
     5 parts of the compound of the present invention are dissolved in an organic solvent to obtain a solution, the solution is sprayed onto 94 parts of kaolin and 1 part of white carbon, and then the solvent is evaporated under reduced pressure. This type of granule can be mixed with animal feed. 
     (Formulation 7: Injection) 
     0.1 to 1 part of the compound of the present invention and 99 to 99.9 parts of peanut oil are uniformly mixed and then sterilized by filtration through a sterilizing filter. 
     (Formulation 8: Pour-on Agent) 
     5 parts of the compound of the present invention, 10 parts of a myristic acid ester and 85 parts of isopropanol are uniformly mixed to obtain a pour-on agent. 
     (Formulation 9: Spot-on Agent) 
     10 to 15 parts of the compound of the present invention, 10 parts of a palmitic acid ester and 75 to 80 parts of isopropanol are uniformly mixed to obtain a spot-on agent. 
     (Formulation 10: Spraying Agent) 
     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 spraying agent. 
     Next, the present invention will be described in more detail by showing synthesis examples. However, the present invention is in no way limited by the following examples. 
     Example 1 
     (Z)-(2-chloro-3-(4-trifluoromethoxy)phenyl)acryloyl)(pyridin-1-ium-1-yl)amide 
     Synthesis of [(Z)-(2-chloro-3-(4-(trifluoromethoxy)phenyl)acryloyl)(pyridin-1-ium-1-yl)amide] 
     [Step 1] 
     Ethyl (Z)-2-chloro-3-(4-(trifluoromethoxy)phenyl) acrylate 
     Synthesis of [ethyl (Z)-2-chloro-3-(4-(trifluoromethoxy)phenyl) acrylate] 
     
       
         
         
             
             
         
       
     
     A Horner-Emmons reagent (3.1 g) was dissolved in THE (10 ml), 60% NaH was added thereto under ice cooling, and the resulting mixture was stirred at room temperature for 30 minutes. 4-(Trifluoromethoxy)benzaldehyde (1.9 g) was added thereto under ice cooling, and the resulting mixture was stirred at room temperature for 1 hour. A saturated aqueous solution of ammonium chloride was added thereto, and the resulting mixture was extracted with ethyl acetate and washed with saturated brine. Thereafter, the organic layer was dried over anhydrous magnesium sulfate, filtered, and then the resulting filtrate was concentrated under reduced pressure. The obtained concentrate was purified by silica gel chromatography to obtain 2.04 g of the title compound at a yield of 69%. 
     [Step 2] 
     (Z)-2-chloro-3-(4-(trifluoromethoxy)phenyl)acrylic acid 
     Synthesis of [(Z)-2-chloro-3-(4-(trifluoromethoxy)phenyl)acrylic acid] 
     
       
         
         
             
             
         
       
     
     Ethyl (Z)-2-chloro-3-(4-(trifluoromethoxy)phenyl) acrylate (1.0 g) was dissolved in a mixed solvent of water (2 ml) and 10% KOH-EtOH (5 ml), and the resulting mixture was heated and stirred under reflux for 3 hours. The resultant was cooled to room temperature, and then the solvent was distilled off. Water and concentrated hydrochloric acid were added to the residue, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed by adding saturated brine. Thereafter, the organic layer was dried over anhydrous magnesium sulfate, filtered, and then the solvent was distilled off to obtain 0.42 g of the title compound at a yield of 75%. 
     [Step 3] 
     (Z)-(2-chloro-3-(4-trifluoromethoxy)phenyl)acryloyl) (pyridin-1-ium-1-yl)amide 
     Synthesis of [(Z)-(2-chloro-3-(4-(trifluoromethoxy)phenyl)acryloyl) (pyridin-1-ium-1-yl)amide] 
     
       
         
         
             
             
         
       
     
     (Z)-2-chloro-3-(4-(trifluoromethoxy)phenyl)acrylic acid (0.64 g) was dissolved in chloroform (5 ml), oxalyl chloride (0.3 ml) and a catalytic amount of DMF were added thereto, and the resulting mixture was stirred at room temperature for 2 hours. The solvent was distilled off from the obtained liquid. Chloroform (5 ml), 1-aminopyridinium iodide (0.53 g) and triethylamine (3 ml) were added to the residue, and the resulting mixture was stirred at room temperature for 3 hours. The obtained liquid was concentrated under reduced pressure. A mixed solvent of ethyl acetate and hexane was added to the obtained concentrate, and the resulting mixture was recrystallized to obtain 0.54 g of the title compound at a yield of 66%. 
     Examples of the compounds of the present invention produced by the same method as in the above Examples are shown in Table 1. Table 1 shows the compounds represented by the formula (I-1) among the compounds of the present invention. In Table 1, Me represents a methyl group. A bond marked with a symbol * used for the notation of Y is bonded to a carbonyl group in a pyridinium salt, and a bond marked with a symbol ** is bonded to a phenyl group. Physical property data of the compounds were entered in the column of “Physical properties”. As the physical property data, refractive indices (nD) or melting points (m.p.) were described. 
     NMR data for the compounds with compound numbers b-36, b-37, b-38, and b-42 are shown below. 
     b-36:  1 H-NMR (CDCl 3 , δ ppm) 2.22 (s, 3H), 4.46 (t, 2H), 6.82 (m, 1H), 6.98 (s, 1H), 7.11 (m, 1H), 7.29 (m, 1H), 7.62 (s, 1H), 7.67 (t, 2H), 7.92 (m, 1H), 8.74 (d, 2H). 
     b-37:  1 H-NMR (CDCl 3 , δ ppm) 2.23 (s, 3H), 7.52 (m, 2H), 7.56 (m, 2H), 7.67-7.71 (m, 1H), 7.95 (t, 1H), 8.75 (m, 2H). 
     b-38:  1 H-NMR (CDCl 3 , δ ppm) 2.21 (s, 3H), 7.17 (d, 2H), 7.41 (d, 2H), 7.63 (s, 1H), 7.68 (t, 2H), 7.93 (t, 1H), 8.73 (m, 2H). 
     b-42:  1 H-NMR (CDCl 3 , δ ppm) 2.25 (s, 3H), 7.56 (d, 2H), 7.67-7.69 (m, 3H), 7.87 (m, 2H), 7.94 (t, 1H), 8.74 (m, 2H), 10.00 (s, 1H). 
     
       
         
         
             
             
         
       
     
     
       
         
           
               
               
               
               
               
               
               
             
               
                 TABLE 1 
               
               
                   
               
               
                 Compound 
                   
                   
                   
                   
                   
                   
               
               
                 Number 
                 (X 1 ) m   
                 A 
                 Y 
                 X 2   
                 (X 3 ) n   
                 Physical Properties 
               
               
                   
               
             
            
               
                 b-1 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 — 
                 m.p. 177-180° C.  
               
               
                   
               
               
                 b-2 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 — 
                 m.p. 117-119° C.  
               
               
                   
               
               
                 b-3 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3 O 
                 — 
                 m.p. 128-130° C.  
               
               
                   
               
               
                 b-4 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 — 
                 m.p. 144-147° C.  
               
               
                   
               
               
                 b-5 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3 O 
                 — 
                 m.p. 147-149° C.  
               
               
                   
               
               
                 b-6 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 — 
                 m.p. 144-145° C.  
               
               
                   
               
               
                 b-7 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 — 
                 m.p. 118-120° C.  
               
               
                   
               
               
                 b-8 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 — 
                 m.p. 145-146° C.  
               
               
                   
               
               
                 b-9 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 — 
                 m.p. 211-213° C.  
               
               
                   
               
               
                 b-10 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 — 
                 m.p. 162-164° C.  
               
               
                   
               
               
                 b-11 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 — 
                 m.p. 125-127° C.  
               
               
                   
               
               
                 b-12 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 — 
                 m.p. 120-122° C.  
               
               
                   
               
               
                 b-13 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3 O 
                 — 
                 m.p. 101-102° C.  
               
               
                   
               
               
                 b-14 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 — 
                 m.p. 140-142° C.  
               
               
                   
               
               
                 b-15 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 2-MeO  
                 — 
                 nD(22.1)1.6263  
               
               
                   
               
               
                 b-16 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 2-MeO  
                 — 
                 m.p. 155-156° C.  
               
               
                   
               
               
                 b-17 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 — 
                 m.p. 98-100° C.  
               
               
                   
               
               
                 b-18 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 — 
                 m.p. 114-114.5° C.  
               
               
                   
               
               
                 b-19 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 — 
                 m.p. 88-90° C.  
               
               
                   
               
               
                 b-20 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3 O 
                 — 
                 m.p. 105-107° C.  
               
               
                   
               
               
                 b-21 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 — 
                 m.p. 149-150° C.  
               
               
                   
               
               
                 b-22 
                 4-CF 3   
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 — 
                 m.p. 247-250° C.  
               
               
                   
               
               
                 b-23 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 — 
                 m.p. 177-178° C.  
               
               
                   
               
               
                 b-24 
                 3-CO 2 Me  
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 — 
                 m.p. 212-214° C.  
               
               
                   
               
               
                 b-25 
                 3-CF 3   
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 — 
                 m.p. 175-178° C.  
               
               
                   
               
               
                 b-26 
                 3-Cl  
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 — 
                 m.p. 169-171° C.  
               
               
                   
               
               
                 b-27 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-MeO  
                 — 
                 m.p. 143-144° C.  
               
               
                   
               
               
                 b-28 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3 O 
                 — 
                 m.p. 130-131° C.  
               
               
                   
               
               
                 b-29 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-MeS 
                 — 
                 m.p. 167-169° C.  
               
               
                   
               
               
                 b-30 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 — 
                 m.p. 171-173° C.  
               
               
                   
               
               
                 b-31 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 3-CF 3   
                 — 
                 m.p. 116-118° C.  
               
               
                   
               
               
                 b-32 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3 OCFHCF 2 O 
                 — 
                 m.p. 150-152° C.  
               
               
                   
               
               
                 b-33 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3 CFHCF 2 O 
                 — 
                 m.p. 142-144° C.  
               
               
                   
               
               
                 b-34 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3 CF 2 CF 2 CF 2 CH═CH 
                 — 
                 m.p. 88-91° C.  
               
               
                   
               
               
                 b-35 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3 CF 2 CH═CH 
                 — 
                 m.p. 65-67° C.  
               
               
                   
               
               
                 b-36 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 3-CF 3 CF 2 CF 2 CH 2 O 
                 — 
                 — 
               
               
                   
               
               
                 b-37 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3 CF 2 CF 2 CF 2   
                 — 
                 — 
               
               
                   
               
               
                 b-38 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3 CF 2 CF 2 OCFHCF 2 O 
                 — 
                 — 
               
               
                   
               
               
                 b-39 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-(CF 3 CF 2 CF 2 CH 2 O—N═CH)  
                 — 
                 m.p. 60-62° C.  
               
               
                   
               
               
                 b-40 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-(CF 3 CF 2 CH 2 O—N═CH) 
                 — 
                 m.p. 62-64° C.  
               
               
                   
               
               
                 b-41 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-(CF 3 CH 2 O—N═CH) 
                 — 
                 m.p. 125-127° C.  
               
               
                   
               
               
                 b-42 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-(O═CH)  
                 — 
                 — 
               
               
                   
               
               
                 b-43 
                 4-Me  
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CHF 2 CF 2 CH 2 O 
                 — 
                 m.p. 136-138° C.  
               
               
                   
               
               
                 b-44 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CHF 2 CF 2 CH 2 O 
                 — 
                 m.p. 133-135° C.  
               
               
                   
               
               
                 b-45 
                 4-Me  
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3 CF 2 CH 2 O 
                 — 
                 m.p. 149-151° C.  
               
               
                   
               
               
                 b-46 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3 CF 2 CH 2 O 
                 — 
                 nD(20.3)1.4769 
               
               
                   
               
               
                 b-47 
                 4-Me  
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3 CH 2 O 
                 — 
                 m.p. 181-183° C.  
               
               
                   
               
               
                 b-48 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3 CH 2 O 
                 — 
                 m.p. 151-153° C.  
               
               
                   
               
               
                 b-49 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 2-Cl 
                 m.p. 108-110° C.  
               
               
                   
               
               
                 b-50 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 3-Cl 
                 m.p. 69-71° C.  
               
               
                   
               
               
                 b-51 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 2-F 
                 m.p. 164-166° C.  
               
               
                   
               
               
                 b-52 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 3-F 
                 m.p. 100-102° C.  
               
               
                   
               
               
                 b-53 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 2-F 
                 m.p. 121-123° C.  
               
               
                   
               
               
                 b-54 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 2-Cl 
                 m.p. 114-116° C.  
               
               
                   
               
               
                 b-55 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 3-Cl 
                 m.p. 117-119° C.  
               
               
                   
               
               
                 b-56 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 4-CF 3   
                 3-F 
                 m.p. 148-150° C. 
               
               
                   
               
            
           
         
       
     
     Further, the present invention will be described in more detail. 
     Example 2 
     Pyridin-1-ium-1-yl (6-(trifluoromethoxy)benzo[d]thiazole-2-carbonyl) amide 
     Synthesis of [pyridin-1-ium-1-yl (6-(trifluoromethoxy)benzo[d]thiazole-2-carbonyl) amide] 
     
       
         
         
             
             
         
       
     
     Ethyl 6-(trifluoromethoxy)benzo[d]thiazole-2-carboxylate (0.18 g) was dissolved in methanol (5 mL), a 2N aqueous solution of sodium hydroxide (2 mL) was added thereto at 0° C., and the resulting mixture was stirred for 30 minutes. Dilute hydrochloric acid was added thereto, and the resulting mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The concentrate was dissolved in dichloromethane (5 mL), oxalyl chloride (0.10 g) and DMF (one drop) were added thereto, and the resulting mixture was stirred for 1 hour. The solvent was distilled off therefrom under reduced pressure, the residue was dissolved in chloroform (5 mL), and 1-aminopyridinium iodide (0.14 g) and triethylamine (0.19 g) were added thereto. Water was added thereto, and the resulting mixture was extracted with dichloromethane. The organic layer was concentrated under reduced pressure. The desired product (0.09 g) was obtained by washing the concentrate with diethyl ether. 
     Examples of the compounds of the present invention produced by the same method as in the above Examples are shown in Table 2. Table 2 shows the compounds represented by the formula (I-2) among the compounds of the present invention. A bond marked with a symbol * in the formula (C) used for the notation of a partial structure of the compound is bonded to a carbonyl group or a thiocarbonyl group in a pyridinium salt. 
     
       
         
         
             
             
         
       
     
     Physical property data of the compounds were entered in the column of “Physical properties”. As the physical property data, refractive indices (nD) or melting points (m.p.) were described. 
     NMR data for the compounds with compound numbers d-29, d-30, d-31, d-37, and d-38 are shown below. 
     d-29:  1 H-NMR (CDCl 3 , δ ppm) 5.01 (t, 2H), 7.72 (m, 2H), 7.95 (t, 1H), 8.43 (d, 1H), 8.77 (d, 1H), 8.81 (d, 2H). 
     d-30:  1 H-NMR (CDCl 3 , 5 ppm) 5.03 (t, 2H), 7.71 (m, 2H), 7.92 (t, 1H), 8.46 (d, 1H), 8.78 (d, 1H), 8.85 (d, 2H). 
     d-31:  1 H-NMR (CDCl 3 , δ ppm) 5.01 (t, 2H), 7.70 (m, 2H), 7.85 (t, 1H), 8.32 (d, 1H), 8.76 (d, 1H), 8.79 (d, 2H). 
     d-37:  1 H-NMR (CDCl 3 , δ ppm) 1.34 (d, 6H), 3.10 (m, 1H), 4.95 (t, 2H), 7.53 (d, 2H), 8.42 (d, 1H), 8.61 (d, 2H), 8.77 (d, 1H). 
     d-38:  1 H-NMR (CDCl 3 , δ ppm) 4.14 (s, 3H), 4.99 (t, 2H), 7.20-7.28 (m, 2H), 8.02 (t, 1H), 8.28 (d, 1H), 8.44 (s, 1H), 8.78 (s, 1H). 
     
       
         
         
             
             
         
       
     
     
       
         
           
               
               
               
               
               
             
               
                 TABLE 2 
               
               
                   
               
               
                       Compound  Number 
                         (X 1 )m 
                         A 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                         Physical Properties 
               
               
                   
               
             
            
               
                 d-1 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 178-182° C. 
               
               
                   
               
               
                 d-2 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 267-270° C. 
               
               
                   
               
               
                 d-3 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 210-213° C. 
               
               
                   
               
               
                 d-4 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 205-207° C. 
               
               
                   
               
               
                 d-7 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 177-178° C. 
               
               
                   
               
               
                 d-8 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 264-266° C. 
               
               
                   
               
               
                 d-10 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 190-192° C. 
               
               
                   
               
               
                 d-11 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 188-190° C. 
               
               
                   
               
               
                 d-12 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 177-179° C. 
               
               
                   
               
               
                 d-14 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 154-156° C. 
               
               
                   
               
               
                 d-15 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 150-152° C. 
               
               
                   
               
               
                 d-16 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 80-82° C. 
               
               
                   
               
               
                 d-17 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 nD(20.9)1.6022 
               
               
                   
               
               
                 d-18 
                 4-Me  
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 155-157° C. 
               
               
                   
               
               
                 d-19 
                 3-Me  
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 134-136° C. 
               
               
                   
               
               
                 d-20 
                 2-Me  
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 53-55° C. 
               
               
                   
               
               
                 d-21 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 177-179° C. 
               
               
                   
               
               
                 d-22 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 140-142° C. 
               
               
                   
               
               
                 d-23 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 136-138° C. 
               
               
                   
               
               
                 d-24 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 122-124° C. 
               
               
                   
               
               
                 d-25 
                 3-Me  
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 nD(20.8)1.5928 
               
               
                   
               
               
                 d-26 
                 2-Me  
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 nD(20.5)1.5844 
               
               
                   
               
               
                 d-27 
                 4-MeO  
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 171-173° C. 
               
               
                   
               
               
                 d-28 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 45-47° C. 
               
               
                   
               
               
                 d-29 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 — 
               
               
                   
               
               
                 d-30 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 — 
               
               
                   
               
               
                 d-31 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 — 
               
               
                   
               
               
                 d-32 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 78-80° C. 
               
               
                   
               
               
                 d-33 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 154-156° C. 
               
               
                   
               
               
                 d-34 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 123-124° C. 
               
               
                   
               
               
                 d-35 
                 4-MeO  
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 110-113° C. 
               
               
                   
               
               
                 d-36 
                 — 
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 117-119° C. 
               
               
                   
               
               
                 d-37 
                 4- i Pr  
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 — 
               
               
                   
               
               
                 d-38 
                 2-MeO  
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 — 
               
               
                   
               
               
                 d-39 
                 4-Me  
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 97-99° C. 
               
               
                   
               
               
                 d-40 
                 3-Cl  
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 102-103° C. 
               
               
                   
               
               
                 d-41 
                 4-CF 3   
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 124-125° C. 
               
               
                   
               
               
                 d-42 
                 3-CF 3   
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 155-156° C. 
               
               
                   
               
               
                 d-43 
                 4-MeO  
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 119-121° C. 
               
               
                   
               
               
                 d-44 
                 3-MeO  
                 O 
                 
                   
                     
                     
                         
                         
                     
                   
                 
                 m.p 109-110° C. 
               
               
                   
               
            
           
         
       
     
     Furthermore, a compound having the following structure (Compound No. d-45) is also shown. d-45 had a melting point of 165-167° C. 
     
       
         
         
             
             
         
       
     
     [Biological Test] 
     The following test examples show that the compounds of the present invention are useful as active ingredients of pest control agents. “Parts” are on a weight basis. 
     (Preparation of Test Emulsion) 
     5 parts by weight of the compound of the present invention, 93.6 parts by weight of dimethylformamide, and 1.4 parts by weight of polyoxyethylene alkylaryl ether were mixed and dissolved to prepare an emulsion (I) containing 5% of an active ingredient. 
     (1) Efficacy Test Against  Mythinma separata  Using Artificial Diet 
     0.8 g of a commercially available artificial diet (Insecta LFS, manufactured by Nosan Corporation) and 1 μl of the emulsion (I) were thoroughly mixed and 0.2 g per each treatment group was packed in a plastic test container (1.4 ml volume) to prepare a test diet. 
     Two second instar larvae of  Mythimna separata  were inoculated for each treatment group and sealed with a plastic lid. It was placed in a thermostatic chamber at 25° C., and the insecticidal rate and food intake were examined on the fifth day. The test was repeated twice. In addition, a test carried out under the same conditions except that the compound of the present invention was removed from the emulsion (I) was designated as a solvent control group. 
     
       
         
           
               
             
               
                 TABLE 3 
               
               
                   
               
               
                 Compound Number 
               
               
                   
               
             
            
               
                   
               
            
           
           
               
               
               
            
               
                 b-5  
                 b-55 
                 d-31 
               
               
                 b-7  
                 b-56 
                 d-35 
               
               
                 b-9  
                 d-4  
                 d-37 
               
               
                 b-11 
                 d-8  
                 d-38 
               
               
                 b-13 
                 d-11 
                 d-39 
               
               
                 b-17 
                 d-12 
                 d-40 
               
               
                 b-18 
                 d-15 
                 d-41 
               
               
                 b-20 
                 d-15 
                 d-42 
               
               
                 b-21 
                 d-18 
                 d-43 
               
               
                 b-23 
                 d-19 
                 d-44 
               
               
                 b-28 
                 d-20 
                 d-45 
               
               
                 b-30 
                 d-21 
                   
               
               
                 b-38 
                 d-22 
                   
               
               
                 b-39 
                 d-24 
                   
               
               
                 b-40 
                 d-25 
                   
               
               
                 b-41 
                 d-26 
                   
               
               
                 b-44 
                 d-27 
                   
               
               
                 b-46 
                 d-28 
                   
               
               
                 b-50 
                 d-29 
                   
               
               
                 b-51 
                 d-30 
               
               
                   
               
            
           
         
       
     
     The compounds shown in Table 3 were tested for efficacy against  Mythinma separata . All of the compounds were effective against  Mythimna separata , with an insecticidal rate of 100% or a food intake of 10% or less, relative to the solvent control group. 
     (2) Efficacy Test Against  Mythimna Separata    
     The emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Maize leaf pieces were immersed in the diluent for 30 seconds. The maize leaf pieces were placed in a petri dish, and five second instar larvae of  Mythimna separata  were released. The petri dish was placed in a thermostatic chamber at a temperature of 25° C. and a humidity of 60%. Viability was evaluated when 6 days had passed since the release of the insects, and the insecticidal rate was calculated. The test was repeated twice. 
     
       
         
           
               
             
               
                 TABLE 4 
               
               
                   
               
               
                 Compound 
               
               
                 Number 
               
               
                   
               
             
            
               
                 b-5  
               
               
                 b-9  
               
               
                 b-20 
               
               
                 b-21 
               
               
                 b-30 
               
               
                 d-2  
               
               
                 d-3  
               
               
                 d-4  
               
               
                 d-8  
               
               
                 d-16 
               
               
                   
               
            
           
         
       
     
     The compounds shown in Table 4 were tested for efficacy against  Mythimna separata . All compounds showed an insecticidal rate of 80% or more against  Mythimna separata.    
     (3) Efficacy Test Against  Spodoptera litura    
     The emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Cabbage leaves were immersed in the diluent for 30 seconds. The cabbage leaves were air dried and placed in a petri dish, and five second instar larvae of  Spodoptera litura  were released. The petri dish was placed in a thermostatic chamber at a temperature of 25° C. and a humidity of 60%. Viability was evaluated when 6 days had passed since the release of the insects, and the insecticidal rate was calculated. The test was repeated twice. 
     
       
         
           
               
             
               
                 TABLE 5 
               
               
                   
               
               
                 Compound Number 
               
               
                   
               
             
            
               
                   
               
            
           
           
               
               
               
            
               
                 b-9  
                 d-8  
                 d-41 
               
               
                 b-11 
                 d-11 
                 d-42 
               
               
                 b-21 
                 d-15 
                 d-43 
               
               
                 b-23 
                 d-18 
                 d-45 
               
               
                 b-30 
                 d-19 
                   
               
               
                 b-31 
                 d-20 
                   
               
               
                 b-32 
                 d-21 
                   
               
               
                 b-37 
                 d-22 
                   
               
               
                 b-38 
                 d-23 
                   
               
               
                 b-39 
                 d-26 
                   
               
               
                 b-41 
                 d-27 
                   
               
               
                 d-1  
                 d-29 
                   
               
               
                 d-2  
                 d-30 
                   
               
               
                 d-3  
                 d-31 
                   
               
               
                 d-4  
                 d-38 
               
               
                   
               
            
           
         
       
     
     The compounds shown in Table 5 were tested for efficacy against  Spodoptera litura . All compounds showed an insecticidal rate of 80% or more against  Spodoptera litura.    
     (4) Efficacy Test Against  Plutella xylostella    
     The emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Cabbage leaves were immersed in the diluent for 30 seconds. The cabbage leaves were air dried and placed in a petri dish, and five second instar larvae of  Plutella xylostella  were released. The petri dish was placed in a thermostatic chamber at a temperature of 25° C. and a humidity of 60%. Viability was evaluated when 3 days had passed since the release of the insects, and the insecticidal rate was calculated. The test was repeated twice. 
     
       
         
           
               
             
               
                 TABLE 6 
               
               
                   
               
               
                 Compound Number 
               
               
                   
               
             
            
               
                   
               
            
           
           
               
               
               
            
               
                   
                 b-5  
                 d-38 
               
               
                   
                 b-7  
                 d-39 
               
               
                   
                 b-21 
                 d-40 
               
               
                   
                 b-44 
                 d-41 
               
               
                   
                 b-50 
                 d-42 
               
               
                   
                 d-4  
                 d-43 
               
               
                   
                 d-8  
                 d-44 
               
               
                   
                 d-16 
                   
               
               
                   
                 d-34 
                   
               
               
                   
                 d-37 
               
               
                   
                   
               
            
           
         
       
     
     The compounds shown in Table 6 were tested for efficacy against  Plutella xylostella . All compounds showed an insecticidal rate of 80% or more against  Plutella xylostella.    
     (5) Efficacy Test Against  Tetranychus urticae    
     Kidney bean plants were raised in No. 3 pots, and five adult females of  Tetranychus urticae  were inoculated on primary leaves. The emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. The diluent was sprayed on the kidney bean plants to prepare a treated group. In addition, a test was carried out under the same conditions except that the compound of the present invention was removed from the emulsion (I) to prepare a solvent control group. The above No. 3 pots were placed in a thermostatic chamber at a temperature of 25° C. and a humidity of 65%, and the inoculated adult females of  Tetranychus urticae  were removed 3 days after spraying, leaving only the eggs laid on the leaves. The number of individuals surviving on the leaves was investigated 10 days after spraying, and the control rate was calculated according to the following formula. The test was repeated twice. 
     
       
         
           
             
               Control 
               ⁢ 
               
                   
               
               ⁢ 
               rate 
               ⁢ 
               
                   
               
               ⁢ 
               
                 ( 
                 % 
                 ) 
               
             
             = 
             
               100 
               × 
               
                 [ 
                 
                   1 
                   - 
                   
                     Nt 
                     ⁢ 
                     
                       / 
                     
                     ⁢ 
                     N 
                     ⁢ 
                     c 
                   
                 
                 ] 
               
             
           
         
       
     
     Nt: number of surviving individuals in treated group, Nc: number of surviving individuals in solvent control group 
     
       
         
           
               
             
               
                 TABLE 7 
               
               
                   
               
               
                 Compound Number 
               
               
                   
               
             
            
               
                 b-9  
               
               
                 b-11 
               
               
                 b-12 
               
               
                 b-13 
               
               
                 b-17 
               
               
                 b-18 
               
               
                 b-19 
               
               
                 b-20 
               
               
                 b-21 
               
               
                 b-31 
               
               
                   
               
            
           
         
       
     
     The compounds shown in Table 7 were tested for efficacy against  Tetranychus urticae . All compounds showed a control rate of 90% or more. 
     (6) Efficacy Test Against  Aphis gossypii    
     Cucumber was sown in No. 3 pots. Adult females of  Aphis gossypii  were released on the cucumber 10 days after germination. The next day, the adult females were removed, leaving the first instar larvae produced. The emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. This diluent was sprayed on the cucumber. Thereafter, the cucumber was placed in a thermostatic chamber at a temperature of 25° C. and a humidity of 60%, and after 5 days, the life and death of  Aphis gossypii  were investigated and the insecticidal rate was determined. 
     The compounds with compound numbers b-14, b-40, b-41, d-11, d-12, d-25, and d-38 were tested for efficacy against  Aphis gossypii . All compounds showed an insecticidal rate of 80% or more. 
     (7) Efficacy Test Against  Helicoverpa armigera    
     The emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Cabbage leaves were immersed in the diluent for 30 seconds. The cabbage leaves were air dried and placed in a petri dish, and five second instar larvae of  Helicoverpa armigera  were released. The petri dish was placed in a thermostatic chamber at a temperature of 25° C. and a humidity of 60%. Viability was evaluated when 6 days had passed since the release of the insects, and the insecticidal rate was calculated. The test was repeated twice. 
     The compounds with compound numbers b-39, b-40, and d-11 were tested for efficacy against  Helicoverpa armigera . All compounds showed an insecticidal rate of 80% or more. 
     (9) Efficacy Test Against  Nilaparvata lugens    
     The emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Rice seedlings were immersed in the diluent for 30 seconds, air dried, and then placed in a plastic case, and five second instar larvae of  Nilaparvata lugens  were released therein. The plastic case was stored in a thermostatic chamber at a temperature of 25° C. and a humidity of 65%, viability was evaluated 10 days after the inoculation, and the insecticidal rate was calculated by the following formula. The test was repeated twice. 
       Insecticidal rate (%)=(number of dead insects/number of tested insects)×100
 
     The compounds with compound numbers b-50, b-55, and b-56 were tested for efficacy against  Nilaparvata lugens . All compounds showed an insecticidal rate of 80% or more. 
     (10) Efficacy Test Against  Tetranychus kanzawai    
     Mung bean plants were raised in No. 3 pots, and five adult females of  Tetranychus kanzawai  were inoculated on primary leaves. The emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. The diluent was sprayed on the mung bean plants to prepare a treated group. In addition, a test was carried out under the same conditions except that the compound of the present invention was removed from the emulsion (I) to prepare a solvent control group. The above No. 3 pots were placed in a thermostatic chamber at a temperature of 25° C. and a humidity of 65%, and the inoculated adult females of  Tetranychus kanzawai  were removed 4 days after spraying, leaving only the eggs laid on the leaves. The number of individuals surviving on the leaves was investigated 11 days after spraying, and the control rate was calculated according to the following formula. The test was repeated twice. 
     
       
         
           
             
               Control 
               ⁢ 
               
                   
               
               ⁢ 
               rate 
               ⁢ 
               
                   
               
               ⁢ 
               
                 ( 
                 % 
                 ) 
               
             
             = 
             
               100 
               × 
               
                 [ 
                 
                   1 
                   - 
                   
                     Nt 
                     ⁢ 
                     
                       / 
                     
                     ⁢ 
                     N 
                     ⁢ 
                     c 
                   
                 
                 ] 
               
             
           
         
       
     
     Nt: number of surviving individuals in treated group, Nc: number of surviving individuals in solvent control group 
     
       
         
           
               
             
               
                 TABLE 8 
               
               
                   
               
               
                 Compound Number 
               
               
                   
               
             
            
               
                   
               
            
           
           
               
               
               
            
               
                 b-38 
                 b-51 
                 d-20 
               
               
                 b-39 
                 b-52 
                 d-21 
               
               
                 b-40 
                 b-53 
                 d-22 
               
               
                 b-41 
                 b-55 
                 d-26 
               
               
                 b-43 
                 b-56 
                 d-28 
               
               
                 b-44 
                 d-11 
                 d-39 
               
               
                 b-45 
                 d-12 
                 d-44 
               
               
                 b-46 
                 d-16 
                   
               
               
                 b-49 
                 d-18 
                   
               
               
                 b-50 
                 d-19 
               
               
                   
               
            
           
         
       
     
     The compounds shown in Table 8 were tested for efficacy against  Tetranychus kanzawai . All compounds showed a control rate of 90% or more. 
     Since those randomly selected from among the pyridinium salts of the present invention exert the above-mentioned effects, it can be understood that the pyridinium salts of the present invention including the compounds that are not shown in examples are compounds having the effects of pest control, acaricidal effects, and in particular, insecticidal effects and the like. 
     INDUSTRIAL APPLICABILITY 
     It is possible to provide a pyridinium salt which is excellent in pest control activity, in particular, insecticidal activity and/or acaricidal activity, excellent in safety and can be synthesized in an industrially favorable manner. In addition, it is possible to provide a pest control agent, an insecticidal or acaricidal agent, an ectoparasite control agent, or an endoparasite control- or exterminating agent containing a pyridinium salt as an active ingredient.