Aryl dihydropyran derivative or salt thereof, pest control agent containing same, and method for use thereof

Abstract

In the production of agricultural and horticultural crops, etc., damages caused by pest insects, etc. are still significant, and, therefore, the development of novel pest control agents has been required due to factors such as the emergence of pest insects resistant to conventional chemicals.　The present invention provides a compound represented by general formula (1) [wherein: X and Y represent an oxygen atom or a sulfur atom; Z represents a hydroxyl group, etc.; R1 represents a hydrogen atom, etc.; R2, R3 and R4 represent a hydrogen atom, etc.; and R5 and Q represent a substituted phenyl group, etc.] or a salt thereof, a pest control agent comprising the compound as an active ingredient, and a method for the use thereof.

Description

Aryldihydropyran derivatives or salts thereof, pest control agents containing said compounds, and methods of using the same

[0001] The present invention relates to an aryldihydropyran derivative or a salt thereof, a pesticide containing said compound as an active ingredient, and a method for using the same.

[0002] Patent Document 1 reports that certain dihydropyrancarboxamide compounds are useful as pharmaceutical compounds. However, this document only discloses an unsubstituted phenyl group as the 6-position substituent on the dihydropyran-2,4-dione ring, and does not describe or suggest the dihydropyran derivatives of the present invention having a phenyl group with one or more substituents and an optionally substituted heterocyclic group, and is completely unaware of the control activity of these compounds against pests such as agricultural and horticultural pests and animal parasites.

[0003] International Publication No. 2008 / 014311

[0004] In the production of useful crops such as agriculture and horticulture, damage caused by pests is severe, and many agricultural and horticultural pest control agents effective against this are on the market. However, due to demands for pesticides that are highly effective against pests resistant to existing drugs, pesticides with physical properties suitable for various labor-saving application methods, pesticides with excellent safety for humans and animals due to reduced acute toxicity, and pesticides with excellent environmental safety due to appropriate soil residual properties, the development of new agricultural and horticultural pest control agents remains one of the important challenges in the agricultural and horticultural field. Furthermore, controlling parasites is also an important challenge in raising animals such as livestock and companion animals (pets). Both parasitic infections themselves and diseases caused by viruses and bacteria transmitted by the parasites cause significant pain to animals, resulting in significant economic losses in livestock. Therefore, there is a need for the development of new animal ectoparasite control agents and animal endoparasite control agents.

[0005] The present inventors have conducted extensive research to develop novel pest control agents, particularly agricultural and horticultural pest control agents, animal ectoparasite control agents, and animal endoparasite control agents. As a result, they have found that compounds having an aryldihydropyran derivative as the carboxylic acid moiety of the carboxamide represented by general formula (1) of the present invention, or salts thereof, are useful as pest control agents, and have completed the present invention.

[0006] That is, the present invention provides a compound represented by the general formula (1): {In the formula, R 1 represents (a1) a hydrogen atom; (a2) a (C1-C6) alkyl group; or (a3) ​​a phenyl group. 2 and R 3 represents (b1) a hydrogen atom; (b2) a (C1-C6) alkyl group; (b3) a (C1-C6) alkoxy(C1-C6) alkyl group; (b4) an N-(C1-C6) alkylamino(C1-C6) alkyl group; (b5) a (C1-C6) alkoxycarbonylamino(C1-C6) alkyl group; or (b6) a phenyl group. R 2 and R 3 may be the same or different. 2 and R 3 may be bonded to each other to form a 3- to 7-membered ring. 4 represents (c1) a hydrogen atom; (c2) a (C1-C6) alkyl group; (c3) a (C3-C6) cycloalkyl group; (c4) a (C1-C6) alkoxy group; or (c5) a (C1-C6) alkylcarbonyl group. 5(d1) a (C1-C6) alkyl group; (d2) a (C2-C6) alkenyl group; (d3) a (C2-C6) alkynyl group; (d4) a (C3-C6) cycloalkyl group; (d5) a halo(C1-C6) alkyl group; (d6) a halo(C2-C6) alkenyl group; (d7) a halo(C2-C6) alkynyl group; (d8) a substituted (C1-C6) alkyl group having 1 to 3 substituents independently selected from the group consisting of a cyano group, a (C3-C6) cycloalkyl group, a (C1-C6) alkoxy group, a (C1-C6) alkylthio group, a halo(C3-C6) cycloalkyl group, a halo(C1-C6) alkoxy group, a halo(C1-C6) alkylthio group, a carboxamide group, a phenylcarbonyl group, and a di(C1-C6) alkylamino group; (d9) a substituted (C3-C6)cycloalkyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a cyano group, a (C3-C6)cycloalkyl group, a (C1-C6)alkoxy group, a (C1-C6)alkylthio group, a (C1-C6)alkyl group, a halo(C3-C6)cycloalkyl group, a halo(C1-C6)alkoxy group, a halo(C1-C6)alkylthio group, and a carboxamide group; (d10) a (C1-C6)alkylsulfonyl group; (d11) an N-(C1-C6)alkylaminosulfonyl group; (d12) a phenylcarbonylamino group; (d13) a substituted phenylcarbonylamino group having on the ring 1 to 3 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d14) a piperidinyl group;(d15) a substituted piperidinyl group having on the ring 1 to 3 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, a halo(C1-C6) alkoxy group, a (C1-C6) alkoxycarbonyl group, and a phenyl(C1-C6) alkoxycarbonyl group; (d16) a morpholinyl group; (d17) a substituted morpholinyl group having on the ring 1 to 3 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d18) a phenyl group;(d19) (a) halogen atom, (b) cyano group, (c) nitro group, (d) hydroxyl group, (e) carboxyl group, (f) (C1-C6) alkyl group, (g) (C1-C6) alkoxy group, (h) (C3-C6) cycloalkyl group, (i) (C1-C6) alkylthio group, (j) (C1-C6) alkylsulfinyl group, (k) (C1-C6) alkylsulfonyl group, (l) halo(C1-C6) alkyl group, (m) halo(C1-C6) alkoxy group, (n) halo(C3-C6) cycloalkyl group, (o) halo(C1-C6) alkylthio group, (p) halo(C1-C6) alkylsulfinyl group, (q) halo(C1-C6) alkylsulfonyl group, (r) (C1-C6)alkoxycarbonyl group, (s) (C1-C6)alkylcarbonylamino group, (t) halo(C1-C6)alkylcarbonylamino group, (u) (C1-C6)alkylsulfonylamino group, (v) halo(C1-C6)alkylsulfonylamino group, (w) N,N-di(C1-C6)alkylcarboxamido group, (x) N-halo(C1-C6)alkylcarboxamido group, (y) (C1-C6)alkylcarbonyl group, (z) (C1-C6)alkylaminosulfonyl group, (aa) SF5 group, (ab) R; 12 - (R 13 -N=)S group (in the formula, R 12 represents a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halo(C1-C6) alkyl group, or a (C1-C6) alkoxy(C1-C6) alkyl group; R 13 represents a hydrogen atom, a cyano group, a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halo(C1-C6) alkyl group, a (C1-C6) alkylcarbonyl group, or a halo(C1-C6) alkylcarbonyl group; (ac) R 12 - (R 13 -N=)O=S group (in the formula, R 12 and R 13are the same as above), (ad) a pyrazolyl group, (ae) a phenoxy group, (af) a phenyl group, and (ag) 1 to 5 substituents independently selected from the group consisting of a substituted phenyl group having on the ring 1 to 5 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group, or (ah) A substituted phenyl group having on the ring a methylenedioxy group which may be substituted with 1 or 2 substituents selected from the group consisting of a halogen atom, a phenyl group, and a (C1-C6) alkyl group, formed by two adjacent substituents taken together (provided that the atom adjacent to the bonding atom of the pyrazolyl group does not include a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkylsulfonyl group, or an R 12 - (R 13 -N=)O=S group (in the formula, R 12 and R 13is the same as above.) is not substituted; (d20) a pyridyl group; (d21) a substituted pyridyl group having on the ring 1 to 4 substituents independently selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, a halo(C1-C6) alkoxy group, a halo(C1-C6) alkylthio group, a halo(C1-C6) alkylsulfinyl group, and a halo(C1-C6) alkylsulfonyl group; (d22) an N-oxo-pyridyl group; (d23) (d24) a substituted N-oxo-pyridyl group having 1 to 3 substituents independently selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, a halo(C1-C6) alkoxy group, a halo(C1-C6) alkylthio group, a halo(C1-C6) alkylsulfinyl group, and a halo(C1-C6) alkylsulfonyl group; (d25) a pyridazinyl group; (d26) a substituted pyridazinyl group having on the ring one to three substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d27) a pyrimidinyl group; a substituted pyrimidinyl group having on the ring 1 to 3 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d28) a pyrazinyl group;(d29) a substituted pyrazinyl group having on the ring one to three substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d30) a triazinyl group; (d31) a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group. (b) a substituted triazinyl group having on the ring one or two substituents independently selected from the group consisting of a (C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (d32) a tetrahydrofuranyl group; (d33) a substituted tetrahydrofuranyl group having on the ring one to three substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group and a halo(C1-C6) alkoxy group; (d34) an oxazolinyl group; (d35) a substituted oxazolinyl group having on the ring 1 to 3 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d36) a thiazolinyl group;(d37) a substituted thiazolinyl group having on the ring one to three substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d38) an oxazolyl group; (d39) a substituted oxazolyl group having on the ring one or two substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d40) a thiazolyl group; (d41) a substituted thiazolyl group having on the ring one or two substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d42) an isoxazolyl group; (d43) a substituted isoxazolyl group having on the ring one or two substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d44) an isothiazolyl group;(d45) a substituted isothiazolyl group having on the ring one or two substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d46) an imidazolyl group; (d47) a substituted imidazolyl group having on the ring one to three substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d48) a pyrazolyl group; (d49) a substituted pyrazolyl group having on the ring one to three substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d50) a triazolyl group; and (d51) a substituted triazolyl group having on the ring one or two substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d52) a tetrazolyl group; (d53) a substituted tetrazolyl group having one substituent on the ring selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group;(d54) a thiadiazolyl group; (d55) a substituted thiadiazolyl group having one substituent on the ring selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d56) a quinolinyl group; (d57) a substituted quinolinyl group having on the ring 1 to 5 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d58) a benzoxazolyl group; (d59) a substituted benzoxazolyl group having on the ring one to four substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d60) a benzothiazolyl group; (d61) a substituted benzothiazolyl group having on the ring 1 to 4 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d62) a benzimidazolyl group;(d63) a substituted benzimidazolyl group having on the ring one to four substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d64) a benzothiadiazolyl group; (d65) a substituted benzothiadiazolyl group having on the ring one to four substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d66) an indazolyl group; (d67) a substituted indazolyl group having 1 to 4 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (d68) an indanyl group; (d69) a halogen atom, a cyano group, ( a substituted indanyl group having on the ring 1 to 4 substituents independently selected from the group consisting of a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d70) a tetrahydronaphthyl group;(d71) a substituted tetrahydronaphthyl group having on the ring one to four substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d72) a tetrahydrofuranyl(C1-C6) alkyl group; (d73) a substituted tetrahydrofuranyl(C1-C6)alkyl group having on the ring one to three substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C3-C6)cycloalkyl group, a (C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group; (d74) a phenyl(C1-C6)alkyl group; (d75) a substituted phenyl(C1-C6)alkyl group having on the ring one to three substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C3-C6)cycloalkyl group, a (C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group; (d76) a thienyl group; (d77) a substituted thienyl group having on the ring 1 to 3 substituents independently selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, a halo(C1-C6) alkoxy group, a halo(C1-C6) alkylthio group, a halo(C1-C6) alkylsulfinyl group, and a halo(C1-C6) alkylsulfonyl group; (d78) a naphthyl group;or (d79) a substituted naphthyl group having on the ring 1 to 3 substituents each independently selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, a halo(C1-C6) alkoxy group, a halo(C1-C6) alkylthio group, a halo(C1-C6) alkylsulfinyl group, and a halo(C1-C6) alkylsulfonyl group. Q is (e1) a substituted phenyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e2) a naphthyl group; (e3) a substituted naphthyl group having 1 to 7 substituents each independently selected from substituent group A on the ring; (e4) a substituted pyridyl group having 1 to 4 substituents each independently selected from substituent group A on the ring; (e5) a pyridazinyl group; (e6) a substituted pyridazinyl group having 1 to 3 substituents each independently selected from substituent group A on the ring; (e7) a pyrimidinyl group; (e8) a substituted pyrimidinyl group having 1 to 3 substituents each independently selected from substituent group A on the ring; (e9) a pyrazinyl group; (e10) a substituted pyrazinyl group having 1 to 3 substituents each independently selected from substituent group A on the ring; (e11) a triazinyl group; (e12) (e14) a substituted 2-oxopyridyl group having on the ring one to two substituents each independently selected from substituent group A; (e15) a furyl group; (e16) a substituted furyl group having on the ring one to three substituents each independently selected from substituent group A; (e17) an isoxazolyl group; (e18) a substituted isoxazolyl group having on the ring one to two substituents each independently selected from substituent group A; (e19) an oxazolyl group; (e20) a substituted oxazolyl group having on the ring one to two substituents each independently selected from substituent group A; (e21) a thienyl group; (e22) a substituted thienyl group having on the ring one to three substituents each independently selected from substituent group A;(e23) an isothiazolyl group; (e24) a substituted isothiazolyl group having one to two substituents independently selected from substituent group A on the ring; (e25) a thiazolyl group; (e26) a substituted thiazolyl group having one to two substituents independently selected from substituent group A on the ring; (e27) an oxadiazolyl group; (e28) a substituted oxadiazolyl group having one substituent independently selected from substituent group A on the ring; (e29) a thiadiazolyl group; (e30) a substituted thiadiazolyl group having one substituent independently selected from substituent group A on the ring; (e31) a pyrrolyl group; (e32) a substituted pyrrolyl group having one to four substituents independently selected from substituent group A on the ring; (e33) a pyrazolyl group; (e34) (e35) an imidazolyl group; (e36) a substituted imidazolyl group having, on the ring, one to three substituents each independently selected from substituent group A; (e37) a triazolyl group; (e38) a substituted triazolyl group having, on the ring, one to two substituents each independently selected from substituent group A; (e39) a tetrazolyl group; (e40) a substituted tetrazolyl group having, on the ring, one substituent each independently selected from substituent group A; (e41) a benzofuranyl group; (e42) a substituted benzofuranyl group having, on the ring, one to five substituents each independently selected from substituent group A; (e43) a benzoxazolyl group; (e44) a substituted benzoxazolyl group having, on the ring, one to four substituents each independently selected from substituent group A; (e45) a benzisoxazolyl group; (e46) a substituted benzisoxazolyl group having on the ring 1 to 4 substituents each independently selected from substituent group A; (e47) a benzothienyl group; (e48) a substituted benzothienyl group having on the ring 1 to 5 substituents each independently selected from substituent group A; (e49) a benzothiazolyl group; (e50) a substituted benzothiazolyl group having on the ring 1 to 4 substituents each independently selected from substituent group A; (e51) a benzisothiazolyl group; (e52) a substituted benzisothiazolyl group having on the ring 1 to 4 substituents each independently selected from substituent group A;(e53) an indolyl group; (e54) a substituted indolyl group having 1 to 6 substituents each independently selected from substituent group A on the ring; (e55) an isoindolyl group; (e56) a substituted isoindolyl group having 1 to 6 substituents each independently selected from substituent group A on the ring; (e57) an indazolyl group; (e58) a substituted indazolyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e59) a benzimidazolyl group; (e60) a substituted benzimidazolyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e61) a benzotriazolyl group; (e62) a substituted benzotriazolyl group having 1 to 4 substituents each independently selected from substituent group A on the ring; (e63) a furopyridyl group; (e64) a substituted furopyridyl group having on the ring one to four substituents each independently selected from substituent group A; (e65) a thienopyridyl group; (e66) a substituted thienopyridyl group having on the ring one to four substituents each independently selected from substituent group A; (e67) an indolizinyl group; (e68) a substituted indolizinyl group having on the ring one to six substituents each independently selected from substituent group A; (e69) a pyrrolopyridyl group; (e70) a substituted pyrrolopyridyl group having on the ring one to five substituents each independently selected from substituent group A; (e71) a pyrrolopyrimidinyl group; (e72) a substituted pyrrolopyrimidinyl group having on the ring one to five substituents each independently selected from substituent group A; (e73) an oxazolopyridyl group; (e74) a substituted oxazolopyridyl group having on the ring one to three substituents each independently selected from substituent group A; (e75) an isoxazolopyridyl group; (e76) a substituted isoxazolopyridyl group having on the ring one to three substituents each independently selected from substituent group A; (e77) a thiazolopyridyl group; (e78) a substituted thiazolopyridyl group having on the ring one to three substituents each independently selected from substituent group A; (e79) an isothiazolopyridyl group; (e80) a substituted isothiazolopyridyl group having on the ring one to three substituents each independently selected from substituent group A; (e81) an imidazopyridyl group;(e82) a substituted imidazopyridyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e83) an imidazopyrimidinyl group; (e84) a substituted imidazopyrimidinyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e85) a pyrazolopyridyl group; (e86) a substituted pyrazolopyridyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e87) a pyrazolopyrimidinyl group; (e88) a substituted pyrazolopyrimidinyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e89) a triazolopyridyl group; (e90) a substituted triazolopyridyl group having 1 to 4 substituents each independently selected from substituent group A on the ring; (e91) a triazolopyrimidinyl group; (e92) a substituted triazolopyrimidinyl group having on the ring one to four substituents each independently selected from substituent group A; (e93) a quinoxalinyl group; (e94) a substituted quinoxalinyl group having on the ring one to five substituents each independently selected from substituent group A; (e95) a quinolinyl group; (e96) a substituted quinolinyl group having on the ring one to six substituents each independently selected from substituent group A; (e97) an isoquinolinyl group; (e98) a substituted isoquinolinyl group having on the ring one to six substituents each independently selected from substituent group A; (e99) a cinnolinyl group; (e100) a substituted cinnolinyl group having on the ring one to five substituents each independently selected from substituent group A; (e101) a phthalazinyl group; (e102) a substituted phthalazinyl group having 1 to 5 substituents independently selected from Substituent group A on the ring; (e103) a quinazolinyl group; (e104) a substituted quinazolinyl group having 1 to 5 substituents independently selected from Substituent group A on the ring; (e105) a naphthyridinyl group;or (e106) a substituted naphthyridinyl group having on the ring 1 to 5 substituents independently selected from Substituent Group A, wherein Q is a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkylsulfonyl group, an N-(C1-C6) alkylaminosulfonyl group, an N,N-di(C1-C6) alkylaminosulfonyl group, or R; 10 - (R 11 -N=)O=S group (in the formula, R 10 represents a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halo(C1-C6) alkyl group, or a (C1-C6) alkoxy(C1-C6) alkyl group; R 11 represents a hydrogen atom, a cyano group, a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halo(C1-C6) alkyl group, a (C1-C6) alkylcarbonyl group, or a halo(C1-C6) alkylcarbonyl group. ) is not substituted. X and Y each independently represent an oxygen atom or a sulfur atom. Z is OR 6 group (in the formula, R 6 represents a hydrogen atom, a (C1-C6) alkyl group, a (C1-C6) alkylcarbonyl group, or a (C1-C6) alkoxycarbonyl group. ), S(O)nR 7 group (wherein n represents 0, 1 or 2, and R 7 represents a hydrogen atom or a (C1-C6) alkyl group. 8 ) R 9 group (in the formula, R 8 and R 9 represents a hydrogen atom, a (C1-C6) alkyl group, a (C1-C6) alkylcarbonyl group, or a (C1-C6) alkoxycarbonyl group; R 8 and R 9may be the same or different. Substituent group A includes: (f1) a halogen atom; (f2) a cyano group; (f3) a nitro group; (f4) a hydroxyl group; (f5) a carboxyl group; (f6) a (C1-C6) alkyl group; (f7) a (C2-C6) alkenyl group; (f8) a (C2-C6) alkynyl group; (f9) a (C1-C6) alkoxy group; (f10) a (C3-C6) cycloalkyl group; (f11) a substituted (C3-C6) cycloalkyl group having on the ring 1 to 3 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, and a (C1-C6) alkylcarbonyl group; (f12) a (C1-C6) alkoxy(C1-C6) alkyl group; (f13) a (C1-C6) alkylthio group; (f14) (C1-C6) alkylsulfinyl group; (f15) (C1-C6) alkylsulfonyl group; (f16) halo(C1-C6) alkyl group; (f17) halo(C2-C6) alkenyl group; (f18) halo(C2-C6) alkynyl group; (f19) halo(C1-C6) alkoxy group; (f20) halo(C3-C6) cycloalkyl group; (f21) halo(C1-C6) alkylthio group; (f22) halo(C1-C6) alkylsulfinyl group; (f23) halo(C1-C6) alkylsulfonyl group; (f24) SF5 group; (f25) (C1-C6) alkylcarbonylamino group; (f26) halo(C1-C6) alkylcarbonylamino group; (f27) (C1-C6) alkylsulfonylamino group; (f28) halo(C1-C6) alkylsulfonylamino group; (f29) N,N-di(C1-C6) alkylcarboxamido group; (f30) N-halo(C1-C6) alkylcarboxamido group; (f31) (C1-C6) alkoxycarbonyl group; (f32) N-(C1-C6) alkylaminosulfonyl group; (f33) N,N-di(C1-C6) alkylaminosulfonyl group; (f34) pyrazolyl group;(f35) a substituted pyrazolyl group having on the ring one to three substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (f36) an oxadiazolyl group; (f37) a substituted oxadiazolyl group having one substituent on the ring independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (f38) a phenyl group; (f39) a substituted phenyl group having on the ring 1 to 5 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (f40) a phenoxy group; (f41) a methylenedioxy group optionally substituted by 1 to 2 substituents selected from the group consisting of a halogen atom, a phenyl group, and a (C1-C6) alkyl group, formed by two adjacent substituents taken together; (f42) R; 10 - (R 11 -N=)O=S group (in the formula, R 10 represents a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halo(C1-C6) alkyl group, or a (C1-C6) alkoxy(C1-C6) alkyl group; R 11 represents a hydrogen atom, a cyano group, a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halo(C1-C6) alkyl group, a (C1-C6) alkylcarbonyl group, or a halo(C1-C6) alkylcarbonyl group; (f43) R 10 - (R 11 -N=)S group (in the formula, R10 and R 11 are the same as above.); (f44) a substituted phenoxy group having on the ring 1 to 5 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (f45) an N,N-di(C1-C6) alkylamino group; (f46) a (C1-C6) alkylcarbonyl group; and (f47) an N-(C1-C6) alkylcarboxamide group.} and salts thereof,

[0007] [2] R 1 is (a1) a hydrogen atom; or (a2) a (C1-C6) alkyl group, and R 2 and R 3 is (b1) a hydrogen atom; (b2) a (C1-C6) alkyl group; (b3) a (C1-C6) alkoxy(C1-C6) alkyl group; (b4) an N-(C1-C6) alkylamino(C1-C6) alkyl group; or (b5) a (C1-C6) alkoxycarbonylamino(C1-C6) alkyl group, and R 2 and R 3 may be the same or different, R 2 and R 3 may be bonded to each other to form a 3- to 7-membered ring, R 4 is (c1) a hydrogen atom; (c2) a (C1-C6) alkyl group; or (c3) a (C3-C6) cycloalkyl group, and R 5(d1) a (C1-C6) alkyl group; (d2) a (C2-C6) alkenyl group; (d3) a (C2-C6) alkynyl group; (d4) a (C3-C6) cycloalkyl group; (d5) a halo(C1-C6) alkyl group; (d8) a substituted (C1-C6) alkyl group having 1 to 3 substituents independently selected from the group consisting of a cyano group, a (C3-C6) cycloalkyl group, a (C1-C6) alkoxy group, a (C1-C6) alkylthio group, a halo(C3-C6) cycloalkyl group, a halo(C1-C6) alkoxy group, a halo(C1-C6) alkylthio group, a carboxamide group, a phenylcarbonyl group, and a di(C1-C6) alkylamino group; (d9) a substituted (C3-C6)cycloalkyl group having on the ring 1 to 3 substituents independently selected from the group consisting of a cyano group, a (C3-C6)cycloalkyl group, a (C1-C6)alkoxy group, a (C1-C6)alkylthio group, a (C1-C6)alkyl group, a halo(C3-C6)cycloalkyl group, a halo(C1-C6)alkoxy group, a halo(C1-C6)alkylthio group, and a carboxamide group; (d18) a phenyl group;(d19) (a) halogen atom, (b) cyano group, (c) nitro group, (d) hydroxyl group, (e) carboxyl group, (f) (C1-C6) alkyl group, (g) (C1-C6) alkoxy group, (h) (C3-C6) cycloalkyl group, (i) (C1-C6) alkylthio group, (j) (C1-C6) alkylsulfinyl group, (k) (C1-C6) alkylsulfonyl group, (l) halo(C1-C6) alkyl group, (m) halo(C1-C6) alkoxy group, (n) halo(C3-C6) cycloalkyl group, (o) halo(C1-C6) alkylthio group, (p) halo(C1-C6) alkylsulfinyl group, (q) halo(C1-C6) alkylsulfonyl group, (r) (C1-C6)alkoxycarbonyl group, (s) (C1-C6)alkylcarbonylamino group, (t) halo(C1-C6)alkylcarbonylamino group, (u) (C1-C6)alkylsulfonylamino group, (v) halo(C1-C6)alkylsulfonylamino group, (w) N,N-di(C1-C6)alkylcarboxamido group, (x) N-halo(C1-C6)alkylcarboxamido group, (y) (C1-C6)alkylcarbonyl group, (z) (C1-C6)alkylaminosulfonyl group, (aa) SF5 group, (ab) R; 12 - (R 13 -N=)S group (in the formula, R 12 represents a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halo(C1-C6) alkyl group, or a (C1-C6) alkoxy(C1-C6) alkyl group; R 13 represents a hydrogen atom, a cyano group, a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halo(C1-C6) alkyl group, a (C1-C6) alkylcarbonyl group, or a halo(C1-C6) alkylcarbonyl group; (ac) R 12 - (R 13 -N=)O=S group (in the formula, R 12 and R 13are the same as above), (ad) a pyrazolyl group, (ae) a phenoxy group, (af) a phenyl group, and (ag) 1 to 5 substituents independently selected from the group consisting of a substituted phenyl group having on the ring 1 to 5 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group, or (ah) A substituted phenyl group having on the ring a methylenedioxy group which may be substituted with 1 or 2 substituents selected from the group consisting of a halogen atom, a phenyl group, and a (C1-C6) alkyl group, formed by two adjacent substituents taken together (provided that the atom adjacent to the bonding atom of the pyrazolyl group does not include a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkylsulfonyl group, or an R 12 - (R 13 -N=)O=S group (in the formula, R 12 and R 13is the same as above.) is not substituted.); (d20) a pyridyl group; (d21) a substituted pyridyl group having 1 to 4 substituents independently selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, a halo(C1-C6) alkoxy group, a halo(C1-C6) alkylthio group, a halo(C1-C6) alkylsulfinyl group, and a halo(C1-C6) alkylsulfonyl group; (d24) a pyridazinyl group; (d25) (d26) a substituted pyridazinyl group having on the ring one to three substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d27) a pyrimidinyl group; a substituted pyrimidinyl group having on the ring one to three substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d28) a pyrazinyl group; (d29) a substituted pyrazinyl group having on the ring 1 to 3 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d30) a triazinyl group;(d31) a substituted triazinyl group having on the ring one or two substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d38) an oxazolyl group; (d39) a substituted oxazolyl group having on the ring one or two substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d40) a thiazolyl group; (d41) a substituted thiazolyl group having on the ring one or two substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d42) an isoxazolyl group; (d43) a substituted isoxazolyl group having on the ring one or two substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d48) a pyrazolyl group; (d49) a substituted pyrazolyl group having on the ring 1 to 3 substituents each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group;(d50) a triazolyl group; (d51) a substituted triazolyl group having on the ring one or two substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d52) a tetrazolyl group; (d53) a substituted tetrazolyl group having one substituent on the ring selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d54) a thiadiazolyl group; (d55) a substituted thiadiazolyl group having one substituent on the ring selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d56) a quinolinyl group; (d57) a substituted quinolinyl group having on the ring 1 to 5 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d60) a benzothiazolyl group; (d61) a substituted benzothiazolyl group having on the ring 1 to 4 substituents each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group;(d62) a benzimidazolyl group; (d63) a substituted benzimidazolyl group having on the ring one to four substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d68) an indanyl group; (d69) a substituted indanyl group having on the ring one to four substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d70) a tetrahydronaphthyl group; (d71) a substituted tetrahydronaphthyl group having on the ring one to four substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (d74) a phenyl(C1-C6) alkyl group; (d75) a substituted phenyl(C1-C6)alkyl group having on the ring 1 to 3 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C3-C6)cycloalkyl group, a (C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group; (d76) a thienyl group;(d77) a substituted thienyl group having 1 to 3 substituents independently selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, a halo(C1-C6) alkoxy group, a halo(C1-C6) alkylthio group, a halo(C1-C6) alkylsulfinyl group, and a halo(C1-C6) alkylsulfonyl group; (d78) a naphthyl group; or (d79) (e1) a substituted phenyl group having on the ring 1 to 3 substituents each independently selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, a halo(C1-C6) alkoxy group, a halo(C1-C6) alkylthio group, a halo(C1-C6) alkylsulfinyl group, and a halo(C1-C6) alkylsulfonyl group, and Q is: (e1) a substituted phenyl group having on the ring 1 to 5 substituents each independently selected from substituent group A; (e2) a naphthyl group; (e3) a substituted naphthyl group having on the ring 1 to 7 substituents each independently selected from substituent group A; (e4) (e11) a triazinyl group; (e12) a substituted triazinyl group having on the ring one to four substituents each independently selected from substituent group A; (e17) an isoxazolyl group; (e18) a substituted isoxazinyl group having on the ring one to three substituents each independently selected from substituent group A; (e19) a pyrazinyl group; (e10) a substituted pyrazinyl group having on the ring one to three substituents each independently selected from substituent group A; (e11) a triazinyl group; (e12) a substituted triazinyl group having on the ring one to two substituents each independently selected from substituent group A; (e17) an isoxazolyl group; (e18) a substituted isoxazolyl group having on the ring one to two substituents each independently selected from substituent group A;(e19) an oxazolyl group; (e20) a substituted oxazolyl group having on the ring one to two substituents each independently selected from substituent group A; (e21) a thienyl group; (e22) a substituted thienyl group having on the ring one to three substituents each independently selected from substituent group A; (e23) an isothiazolyl group; (e24) a substituted isothiazolyl group having on the ring one to two substituents each independently selected from substituent group A; (e25) a thiazolyl group; (e26) a substituted thiazolyl group having on the ring one to two substituents each independently selected from substituent group A; (e41) a benzofuranyl group; (e42) a substituted benzofuranyl group having on the ring one to five substituents each independently selected from substituent group A; (e43) a benzoxazolyl group; (e44) A substituted benzoxazolyl group having on the ring one to four substituents each independently selected from substituent group A; (e45) a benzisoxazolyl group; (e46) a substituted benzisoxazolyl group having on the ring one to four substituents each independently selected from substituent group A; (e47) a benzothienyl group; (e48) a substituted benzothienyl group having on the ring one to five substituents each independently selected from substituent group A; (e49) a benzothiazolyl group; (e50) a substituted benzothiazolyl group having on the ring one to four substituents each independently selected from substituent group A; (e51) a benzisothiazolyl group; (e52) a substituted benzisothiazolyl group having on the ring one to four substituents each independently selected from substituent group A; (e53) an indolyl group; (e54) a substituted indolyl group having on the ring one to six substituents each independently selected from substituent group A; (e55) an isoindolyl group; (e56) a substituted isoindolyl group having 1 to 6 substituents independently selected from the substituent group A on the ring; (e57) an indazolyl group; (e58) a substituted indazolyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (e59) a benzimidazolyl group; (e60) a substituted benzimidazolyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (e61) a benzotriazolyl group;(e62) a substituted benzotriazolyl group having 1 to 4 substituents each independently selected from substituent group A on the ring; (e65) a thienopyridyl group; (e66) a substituted thienopyridyl group having 1 to 4 substituents each independently selected from substituent group A on the ring; (e67) an indolizinyl group; (e68) a substituted indolizinyl group having 1 to 6 substituents each independently selected from substituent group A on the ring; (e69) a pyrrolopyridyl group; (e70) a substituted pyrrolopyridyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e71) a pyrrolopyrimidinyl group; (e72) a substituted pyrrolopyrimidinyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e77) a thiazolopyridyl group; (e78) a substituted thiazolopyridyl group having on the ring one to three substituents each independently selected from substituent group A; (e79) an isothiazolopyridyl group; (e80) a substituted isothiazolopyridyl group having on the ring one to three substituents each independently selected from substituent group A; (e93) a quinoxalinyl group; (e94) a substituted quinoxalinyl group having on the ring one to five substituents each independently selected from substituent group A; (e95) a quinolinyl group; (e96) a substituted quinolinyl group having on the ring one to six substituents each independently selected from substituent group A; (e97) an isoquinolinyl group; (e98) a substituted isoquinolinyl group having on the ring one to six substituents each independently selected from substituent group A; (e99) a cinnolinyl group; (e100) a substituted cinnolinyl group having on the ring 1 to 5 substituents each independently selected from substituent group A; (e101) a phthalazinyl group; (e102) a substituted phthalazinyl group having on the ring 1 to 5 substituents each independently selected from substituent group A; (e103) a quinazolinyl group; (e104) a substituted quinazolinyl group having on the ring 1 to 5 substituents each independently selected from substituent group A; (e105) a naphthyridinyl group; or (e106) a substituted naphthyridinyl group having on the ring 1 to 5 substituents each independently selected from substituent group A, 6 group (in the formula, R6 represents a hydrogen atom, a (C1-C6) alkyl group, a (C1-C6) alkylcarbonyl group, or a (C1-C6) alkoxycarbonyl group. 7 group (wherein n represents 0, 1 or 2, and R 7represents a hydrogen atom or a (C1-C6) alkyl group. (f10) a (C3-C6)cycloalkyl group; (f11) a substituted (C3-C6)cycloalkyl group having on the ring 1 to 3 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, and a (C1-C6)alkylcarbonyl group; (f12) a (C1-C6)alkoxy(C1-C6)alkyl group; (f13) a (C1-C6)alkylthio group; (f14) (C1-C6) alkylsulfinyl group; (f15) (C1-C6) alkylsulfonyl group; (f16) halo(C1-C6) alkyl group; (f19) halo(C1-C6) alkoxy group; (f20) halo(C3-C6) cycloalkyl group; (f21) halo(C1-C6) alkylthio group; (f22) halo(C1-C6) alkylsulfinyl group; (f23) halo(C1-C6) alkylsulfonyl group; (f24) SF5 group; (f25) (C1-C6) alkylcarbonylamino group; (f26) halo(C1-C6) alkylcarbonylamino group; (f27) (C1-C6) alkylsulfonylamino group; (f28) halo(C1-C6) alkylsulfonylamino group; (f29) N,N-di(C1-C6)alkylcarboxamido group; (f30) N-halo(C1-C6)alkylcarboxamido group; (f31) (C1-C6)alkoxycarbonyl group; (f32) N-(C1-C6)alkylaminosulfonyl group; (f34) pyrazolyl group; (f35) a substituted pyrazolyl group having on the ring 1 to 3 substituents each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C3-C6)cycloalkyl group, a (C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group; (f38) a phenyl group;(f39) a substituted phenyl group having 1 to 5 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group on the ring; (f40) a phenoxy group; (f41) a methylenedioxy group optionally substituted by 1 to 2 substituents selected from the group consisting of a halogen atom, a phenyl group, and a (C1-C6) alkyl group, formed by two adjacent substituents taken together; (f42) R; 10 - (R 11 -N=)O=S group (in the formula, R 10 represents a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halo(C1-C6) alkyl group, or a (C1-C6) alkoxy(C1-C6) alkyl group; R 11 represents a hydrogen atom, a cyano group, a (C1-C6) alkyl group, a (C3-C6) cycloalkyl group, a halo(C1-C6) alkyl group, a (C1-C6) alkylcarbonyl group, or a halo(C1-C6) alkylcarbonyl group; (f43) R 10 - (R 11 -N=)S group (in the formula, R 10 and R 11 are the same as above; (f44) a substituted phenoxy group having on the ring 1 to 5 substituents independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo(C1-C6) alkyl group, and a halo(C1-C6) alkoxy group; (f45) an N,N-di(C1-C6) alkylamino group; (f46) a (C1-C6) alkylcarbonyl group; and (f47) an N-(C1-C6) alkylcarboxamide group,

[0008] [3] R 1 (a1) is a hydrogen atom, and R 2 and R3 is (b1) a hydrogen atom; (b2) a (C1-C6) alkyl group; or (b5) a (C1-C6) alkoxycarbonylamino(C1-C6) alkyl group, and R 2 and R 3 may be the same or different, R 2 and R 3 may be bonded to each other to form a 3- to 6-membered ring, R 4 (c1) is a hydrogen atom, and R 5(d4) a (C3-C6) cycloalkyl group; (d18) a phenyl group; (d19') (a) a halogen atom, (b) a cyano group, (c) a nitro group, (f) a (C1-C6) alkyl group, (g) a (C1-C6) alkoxy group, (h) a (C3-C6) cycloalkyl group, (i) a (C1-C6) alkylthio group, (j) a (C1-C6) alkylsulfinyl group, (k) a (C1-C6) alkylsulfonyl group, (l) a halo(C1-C6) alkyl group, (m) a halo(C1-C6) alkoxy group, (o) a halo(C1-C6) alkylthio group, (p) a halo(C1-C6) alkylsulfinyl group, (q) a halo(C1-C6) alkylsulfonyl group, (r) a (C1-C6) alkoxycarbonyl group, (s) (C1-C6) alkylcarbonylamino group, (u) (C1-C6) alkylsulfonylamino group, (x) N-halo(C1-C6) alkylcarboxamido group, (y) (C1-C6) alkylcarbonyl group, (z) (C1-C6) alkylaminosulfonyl group, (aa) SF5 group, and (ae) phenoxy group, or (ah') a substituted phenyl group having on the ring a methylenedioxy group formed by two adjacent substituents taken together; (d20) a pyridyl group; (d21') a substituted pyridyl group having on the ring one to four substituents independently selected from halogen atoms; (d25') a substituted pyridazinyl group having on the ring one to three substituents independently selected from halogen atoms; (d27') (d29') a substituted pyrimidinyl group having on the ring one to three substituents each independently selected from halogen atoms; (d30) a triazinyl group; (d38) an oxazolyl group; (d40) a thiazolyl group; (d43') a substituted isoxazolyl group having on the ring one to two substituents each independently selected from (C1-C6) alkyl groups; (d49') a substituted pyrazolyl group having on the ring one to three substituents each independently selected from (C1-C6) alkyl groups; (d50) a triazolyl group; (d52) a tetrazolyl group;(d55') a substituted thiadiazolyl group having one substituent on the ring selected from halo(C1-C6)alkyl groups; (d56) a quinolinyl group; (d60) a benzothiazolyl group; (d63') a substituted benzimidazolyl group having 1 to 4 substituents each independently selected from (C1-C6)alkyl groups on the ring; or (d76) a thienyl group; wherein Q is (e1) a substituted phenyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e2) a naphthyl group; (e4) a substituted pyridyl group having 1 to 4 substituents each independently selected from substituent group A on the ring; (e18) a substituted isoxazolyl group having 1 to 2 substituents each independently selected from substituent group A on the ring; (e19) an oxazolyl group; or (e23) an isothiazolyl group; X and Y are each independently an oxygen atom or a sulfur atom, and Z is OR; 6 group (in the formula, R 6 represents a hydrogen atom.), and Substituent group A is selected from the group consisting of (f1) a halogen atom; (f2) a cyano group; (f3) a nitro group; (f5) a carboxyl group; (f6) a (C1-C6) alkyl group; (f9) a (C1-C6) alkoxy group; (f13) a (C1-C6) alkylthio group; (f14) a (C1-C6) alkylsulfinyl group; (f15) a (C1-C6) alkylsulfonyl group; (f16) a halo(C1-C6) alkyl group; (f19) a halo(C1-C6) alkoxy group; (f21) a halo(C1-C6) alkylthio group; (f22) a halo(C1-C6) alkylsulfinyl group; (f30) an N-halo(C1-C6) alkylcarboxamide group; (f31) (C1-C6) alkoxycarbonyl group; (f38) phenyl group; (f41') methylenedioxy group formed by two adjacent substituents taken together; (f43') R 10 - (R 11 -N=)S group (in the formula, R 10 represents a (C1-C6) alkyl group, and R 11 represents a cyano group; and (f44') a substituted phenoxy group having 1 to 5 cyano groups on the ring, the compound according to [1] or [2] or a salt thereof,

[0009] [4] A pest control agent comprising the compound according to any one of [1] to [3] or a salt thereof as an active ingredient; [5] An agricultural and horticultural pest control agent comprising the compound according to any one of [1] to [3] or a salt thereof as an active ingredient; [6] An animal ectoparasite control agent comprising the compound according to any one of [1] to [3] or a salt thereof as an active ingredient; [7] An animal endoparasite control agent comprising the compound according to any one of [1] to [3] or a salt thereof as an active ingredient; [8] A method for controlling agricultural and horticultural pests, comprising treating a plant or soil with an effective amount of the agricultural and horticultural pest control agent according to [5]; [9] A method for controlling animal ectoparasites, comprising orally or parenterally administering to a target animal an effective amount of the animal ectoparasite control agent according to [6];

[10] A method for controlling endoparasites in animals, comprising orally or parenterally administering to a target animal an effective amount of the endoparasite control agent for animals according to [7].

[11] Use of the compound or a salt thereof according to any one of [1] to [3] as a pest control agent.

[0010] The compound of the present invention or a salt thereof provides an aryldihydropyran derivative represented by the general formula (1) which has excellent effects as a pest control agent.

[0011] In the definition of the general formula (1) of the compound of the present invention, "halo" means a "halogen atom" and represents a chlorine atom, bromine atom, iodine atom, or fluorine atom.

[0012] The term "(C1-C6) alkyl group" refers to a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, such as a methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group, tertiary pentyl group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, normal hexyl group, isohexyl group, 2-hexyl group, 3-hexyl group, 2-methylpentyl group, 3-methylpentyl group, 1,1,2-trimethylpropyl group, or 3,3-dimethylbutyl group.

[0013] The term "(C2-C6) alkenyl group" refers to a linear or branched alkenyl group having 2 to 6 carbon atoms, such as a vinyl group, an allyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 2-methyl-2-propenyl group, a 1-methyl-2-propenyl group, a 2-methyl-1-propenyl group, a pentenyl group, a 1-hexenyl group, or a 3,3-dimethyl-1-butenyl group. 6) The term "alkynyl group" refers to a straight-chain or branched-chain alkynyl group having 2 to 6 carbon atoms, 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, a 3-methyl-1-propynyl group, a 2-methyl-3-propynyl group, a pentynyl group, a 1-hexynyl group, a 3-methyl-1-butynyl group, or a 3,3-dimethyl-1-butynyl group.

[0014] The term "(C3-C6) cycloalkyl group" refers to a cyclic alkyl group having 3 to 6 carbon atoms, such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and the term "(C1-C6) alkoxy group" refers to a straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms, such as a methoxy group, an ethoxy group, a normal propoxy group, an isopropoxy group, a normal butoxy group, a secondary butoxy group, a tertiary butoxy group, a normal pentyloxy group, an isopentyloxy group, a tertiary pentyloxy group, a neopentyloxy group, a 2,3-dimethylpropyloxy group, a 1-ethylpropyloxy group, a 1-methylbutyloxy group, a normal hexyloxy group, an isohexyloxy group, or a 1,1,2-trimethylpropyloxy group.

[0015] The "(C1-C6) alkylthio group" refers to a straight-chain or branched-chain alkylthio group having 1 to 6 carbon atoms, such as a methylthio group, an ethylthio group, a normal propylthio group, an isopropylthio group, a normal butylthio group, a secondary butylthio group, a tertiary butylthio group, a normal pentylthio group, an isopentylthio group, a tertiary pentylthio group, a neopentylthio group, a 2,3-dimethylpropylthio group, a 1-ethylpropylthio group, a 1-methylbutylthio group, a normal hexylthio group, an isohexylthio group, or a 1,1,2-trimethylpropylthio group.

[0016] The "(C1-C6) alkylsulfinyl group" refers to a linear or branched alkylsulfinyl group having 1 to 6 carbon atoms, such as a methylsulfinyl group, ethylsulfinyl group, normal propylsulfinyl group, isopropylsulfinyl group, normal butylsulfinyl group, secondary butylsulfinyl group, tertiary butylsulfinyl group, normal pentylsulfinyl group, isopentylsulfinyl group, tertiary pentylsulfinyl group, neopentylsulfinyl group, 2,3-dimethylpropylsulfinyl group, 1-ethylpropylsulfinyl group, 1-methylbutylsulfinyl group, normal hexylsulfinyl group, isohexylsulfinyl group, or 1,1,2-trimethylpropylsulfinyl group.

[0017] Examples of the "(C1-C6) alkylsulfonyl group" include linear or branched alkylsulfonyl groups having 1 to 6 carbon atoms, such as methylsulfonyl group, ethylsulfonyl group, normal propylsulfonyl group, isopropylsulfonyl group, normal butylsulfonyl group, secondary butylsulfonyl group, tertiary butylsulfonyl group, normal pentylsulfonyl group, isopentylsulfonyl group, tertiary pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1-ethylpropylsulfonyl group, 1-methylbutylsulfonyl group, normal hexylsulfonyl group, isohexylsulfonyl group, and 1,1,2-trimethylpropylsulfonyl group.

[0018] The term "(C1-C6) alkylcarbonyl group" refers to an alkylcarbonyl group having 2 to 7 carbon atoms, such as an acetyl group, a propanoyl group, a butanoyl group, a 2-methylpropanoyl group, a pentanoyl group, a 2-methylbutanoyl group, a 3-methylbutanoyl group, a pivaloyl group, or a hexanoyl group, which has the above-mentioned (C1-C6) alkyl group.

[0019] The term "(C1-C6) alkylcarbonylamino group" refers to an alkylcarbonylamino group having 2 to 7 carbon atoms, such as an alkylcarbonylamino group having the above-mentioned (C1-C6) alkyl group, such as an acetylamino group, a propanoylamino group, a butanoylamino group, a 2-methylpropanoylamino group, a pentanoylamino group, a 2-methylbutanoylamino group, a 3-methylbutanoylamino group, a pivaloylamino group, or a hexanoylamino group.

[0020] Examples of the "(C1-C6) alkylsulfonylamino group" include linear or branched alkylsulfonylamino groups having 1 to 6 carbon atoms, such as methylsulfonylamino, ethylsulfonylamino, normal propylsulfonylamino, isopropylsulfonylamino, normal butylsulfonylamino, secondary butylsulfonylamino, tertiary butylsulfonylamino, normal pentylsulfonylamino, isopentylsulfonylamino, tertiary pentylsulfonylamino, neopentylsulfonylamino, 2,3-dimethylpropylsulfonylamino, 1-ethylpropylsulfonylamino, 1-methylbutylsulfonylamino, normal hexylsulfonylamino, isohexylsulfonylamino, and 1,1,2-trimethylpropylsulfonylamino.

[0021] The term "N-(C1-C6) alkylcarboxamide group" refers to an alkylcarboxamide group having 2 to 7 carbon atoms and having a linear or branched alkyl group having 1 to 6 carbon atoms, such as an N-methylcarboxamide group, N-ethylcarboxamide group, N-normal propylcarboxamide group, N-isopropylcarboxamide group, N-normal butylcarboxamide group, N-isobutylcarboxamide group, N-secondary butylcarboxamide group, N-tertiary butylcarboxamide group, N-normal pentylcarboxamide group, N-isopentylcarboxamide group, N-tertiary pentylcarboxamide group, N-neopenthicarboxamide group, N-normal hexylcarboxamide group, or N-isohexylcarboxamide group.

[0022] Examples of the "N,N-di(C1-C6)alkylcarboxamide group" include an N,N-dimethylcarboxamide group, an N,N-diethylcarboxamide group, an N,N-dinormalpropylcarboxamide group, an N,N-diisopropylcarboxamide group, an N,N-dinormalbutylcarboxamide group, an N,N-disecondarybutylcarboxamide group, an N,N-ditertiarybutylcarboxamide group, an N-methyl-N-ethylcarboxamide group, an N-methyl-N-normalpropylcarboxamide group, an N-methyl-N-isopropylcarboxamide group, an N-methyl-N-normalbutylcarboxamide group, an N-methyl-N-secondarybutylcarboxamide group, and an N-methyl-N-tertiarybutyl and N-methyl-N-(1,1,2-trimethylpropyl)carboxamide groups, such as a carboxamide group, an N-methyl-N-normal pentylcarboxamide group, an N-methyl-N-isopentylcarboxamide group, an N-methyl-N-tertiary pentylcarboxamide group, an N-methyl-N-neopentylcarboxamide group, an N-methyl-N-(2,3-dimethylpropyl)carboxamide group, an N-methyl-N-(1-ethylpropyl)carboxamide group, an N-methyl-N-(1-methylbutyl)carboxamide group, an N-methyl-N-normal hexylcarboxamide group, an N-methyl-N-isohexylcarboxamide group, or an N-methyl-N-(1,1,2-trimethylpropyl)carboxamide group.

[0023] The term "(C1-C6)alkoxycarbonyl group" refers to an alkoxycarbonyl group having 2 to 7 carbon atoms, such as an alkoxycarbonyl group having the above-mentioned (C1-C6)alkoxy group, such as a methoxycarbonyl group, an ethoxycarbonyl group, a normal propoxycarbonyl group, an isopropoxycarbonyl group, a normal butoxycarbonyl group, an isobutoxycarbonyl group, a secondary butoxycarbonyl group, a tertiary butoxycarbonyl group, or a pentyloxycarbonyl group.

[0024] Examples of the "N-(C1-C6) alkylaminosulfonyl group" include linear or branched alkylaminosulfonyl groups having 1 to 6 carbon atoms, such as N-methylaminosulfonyl group, N-ethylaminosulfonyl group, N-normal propylaminosulfonyl group, N-isopropylaminosulfonyl group, N-normal butylaminosulfonyl group, N-secondary butylaminosulfonyl group, N-tertiary butylaminosulfonyl group, N-normal pentylaminosulfonyl group, N-isopentylaminosulfonyl group, N-tertiary pentylaminosulfonyl group, N-neopentylaminosulfonyl group, N-(2,3-dimethylpropyl)aminosulfonyl group, N-(1-ethylpropyl)aminosulfonyl group, N-(1-methylbutyl)aminosulfonyl group, N-normal hexylaminosulfonyl group, N-isohexylaminosulfonyl group, and N-(1,1,2-trimethylpropyl)aminosulfonyl group.

[0025] Examples of the "N,N-di(C1-C6)alkylaminosulfonyl group" include an N,N-dimethylaminosulfonyl group, an N,N-diethylaminosulfonyl group, an N,N-di-normal propylaminosulfonyl group, an N,N-diisopropylaminosulfonyl group, an N,N-di-normal butylaminosulfonyl group, an N,N-di-secondary butylaminosulfonyl group, an N,N-di-tertiary butylaminosulfonyl group, an N-methyl-N-ethylaminosulfonyl group, an N-methyl-N-normal propylaminosulfonyl group, an N-methyl-N-isopropylaminosulfonyl group, an N-methyl-N-normal butylaminosulfonyl group, an N-methyl-N-secondary butylaminosulfonyl group, an N-methyl-N ...tertiary butylaminosulfonyl group, an N-methyl-N-ethylaminos and the like.

[0026] One or more halogen atoms may be substituted at substitutable positions in the above-mentioned "(C1-C6) alkyl group," "(C2-C6) alkenyl group," "(C2-C6) alkynyl group," "(C1-C6) alkoxy group," "(C1-C6) alkylthio group," "(C1-C6) alkylsulfinyl group," "(C1-C6) alkylsulfonyl group," "(C3-C6) cycloalkyl group," "(C1-C6) alkylcarbonylamino group," "(C1-C6) alkylsulfonylamino group," "N-(C1-C6) alkylcarboxamide group," "N,N-di(C1-C6) alkylcarboxamide group," etc., and when there are two or more halogen atoms substituted, the halogen atoms may be the same or different.

[0027] They are respectively represented as "halo(C1-C6)alkyl group," "halo(C2-C6)alkenyl group," "halo(C2-C6)alkynyl group," "halo(C1-C6)alkoxy group," "halo(C1-C6)alkylthio group," "halo(C1-C6)alkylsulfinyl group," "halo(C1-C6)alkylsulfonyl group," "halo(C3-C6)cycloalkyl group," "halo(C1-C6)alkylcarbonylamino group," "halo(C1-C6)alkylsulfonylamino group," "N-halo(C1-C6)alkylcarboxamide group," "N,N-dihalo(C1-C6)alkylcarboxamide group," etc.

[0028] Expressions such as "(C1-C6)", "(C2-C6)", "(C3-C6)" and the like indicate the range of carbon atoms of various substituents. Furthermore, the above definitions can also be applied to groups to which the above substituents are linked. For example, "(C1-C6)alkoxy(C1-C6)alkyl" indicates that a linear or branched alkoxy group having 1 to 6 carbon atoms is bonded to a linear or branched alkyl group having 1 to 6 carbon atoms.

[0029] R 2 and R 3 may be bonded to each other to form a 3- to 7-membered ring. The "3- to 7-membered ring" is 2 and a group obtained by removing any hydrogen atom from R 3 is a ring formed by bonding with a group obtained by removing any hydrogen atom from R 2 is a methyl group, and R 3 is a 2-methoxyethyl group, and R 2 and a group obtained by removing a hydrogen atom from a methyl group of R 3 When a group formed by removing a hydrogen atom from a methoxy group in the 2-methoxyethyl group of the formula (I) is bonded to the 2-methoxyethyl group, tetrahydropyran is formed. Examples of the "3- to 7-membered ring" include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, tetrahydrofuran, tetrahydropyran, pyrrolidine whose nitrogen atom may be protected with a (C1-C6)alkoxycarbonyl group, and piperidine whose nitrogen atom may be protected with a (C1-C6)alkoxycarbonyl group.

[0030] Examples of salts of the compound represented by general formula (1) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate; organic acid salts such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, and paratoluenesulfonate; and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and trimethylammonium.

[0031] The compound represented by general formula (1) of the present invention and its salts may have one or more asymmetric centers in their structural formula, and may exist as two or more optical isomers and diastereomers, and the present invention encompasses all of the optical isomers and mixtures containing them in any ratio. Furthermore, the compound represented by general formula (1) of the present invention and its salts may have two geometric isomers derived from a carbon-carbon double bond in their structural formula, and the present invention encompasses all of the geometric isomers and mixtures containing them in any ratio. Furthermore, the compound represented by general formula (1) of the present invention and its salts may have multiple tautomers, and the present invention encompasses all of the tautomers and mixtures containing them in any ratio.

[0032] In the compound represented by general formula (1) of the present invention, preferred embodiments are shown below. 1 As the group, the above group (a1) or (a2) is preferred, and the above group (a1) is more preferred.

[0033] In general formula (1), R 2 and R 3 are preferably the same or different and are the groups (b1), (b2), (b3), (b4), or (b5) above, and R 2 and R 3 are preferably bonded to each other to form a 3- to 7-membered ring, and the above groups (b1), (b2), or (b5) are more preferred, and R 2 and R 3 However, it is more preferable that they are bonded to each other to form a 3- to 6-membered ring.

[0034] In general formula (1), R 4 is preferably the above group (c1), (c2), or (c3), and more preferably (c1) a hydrogen atom.

[0035] In general formula (1), R 5 The above are (d1), (d2), (d3), (d4), (d5), (d8), (d9), (d18), (d19), (d20), (d21), (d24), (d25), (d26), (d27), (d28), (d29), (d30), (d31), (d38), (d39), (d40), (d41), (d42), (d43), ( groups d48), (d49), (d50), (d51), (d52), (d53), (d54), (d55), (d56), (d57), (d60), (d61), (d62), (d63), (d68), (d69), (d70), (d71), (d74), (d75), (d76), (d77), (d78) or (d79), The above groups (d4), (d18), (d19'), (d20), (d21'), (d25'), (d27'), (d29'), (d30), (d40), (d43'), (d49'), (d50), (d52), (d55'), (d56), (d60), (d63'), and (d76) are more preferred.

[0036] In general formula (1), Q may be any of the above (e1), (e2), (e3), (e4), (e5), (e6), (e7), (e8), (e9), (e10), (e11), (e12), (e17), (e18), (e19), (e20), (e21), (e22), (e23), (e24), (e25), (e26), (e41), (e42), (e43), (e44), (e45), (e46), (e47), (e48), (e49), (e50), (e51), (e52), (e53), (e 54), (e55), (e56), (e57), (e58), (e59), (e60), (e61), (e62), (e65), (e66), (e67), (e68), (e69), (e70), (e71), (e72), (e77), (e78), (e79), (e80), (e93), (e94), (e95), (e96), (e97), (e98), (e99), (e100), (e101), (e102), (e103), (e104), (e105) or (e106), The above groups (e1), (e2), (e4), (e18), (e19) or (e23) are more preferred.

[0037] In general formula (1), it is preferable that X is an oxygen atom and Y is an oxygen atom. It is also preferable that X is an oxygen atom and Y is a sulfur atom in general formula (1).

[0038] In the general formula (1), Z is OR 6 group (in the formula, R 6 represents a hydrogen atom, a (C1-C6) alkyl group, a (C1-C6) alkylcarbonyl group, or a (C1-C6) alkoxycarbonyl group. 7 group (wherein n represents 0, 1 or 2, and R 7 represents a hydrogen atom or a (C1-C6) alkyl group, and OR 6 group (in the formula, R 6 represents a hydrogen atom.) is more preferred.

[0039] In general formula (1), the substituent group A includes the above-mentioned (f1), (f2), (f3), (f5), (f6), (f7), (f8), (f9), (f10), (f11), (f12), (f13), (f14), (f15), (f16), (f19), (f20), (f21), (f22), (f23), (f 24), (f25), (f26), (f27), (f28), (f29), (f30), ​​(f31), (f32), (f34), (f35), (f38), (f39), (f40), (f41), (f42), (f43), (f44), (f45), (f46), and (f47), It is more preferable that the groups are (f1), (f2), (f3), (f5), (f6), (f9), (f13), (f14), (f15), (f16), (f19), (f21), (f22), (f30), ​​(f31), (f38), (f41′), (f43′), and (f44′).

[0040] The various compounds of the present invention can be produced, for example, by the following production methods, but the present invention is not limited to these.

[0041] Production Method 1 The compound of the present invention represented by the general formula (1-1) can be produced from the compound of the general formula (2) by the following step [a].

[0042] {In the formula, R 1 , R 2 , R 3 , R 5 , Q and Y are the same as above.}

[0043] Production Method in Step [a] The compound represented by general formula (1-1) of the present invention can be produced by reacting the compound represented by general formula (2) with the compound represented by general formula (3) in the presence of a base and an inert solvent.

[0044] Examples of the base that can be used in this reaction include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; carbonates such as lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, calcium carbonate, magnesium carbonate, and cesium carbonate; acetates such as lithium acetate, sodium acetate, and potassium acetate; and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, N,N-diisopropylethylamine, and diazabicycloundecene (DBU). The amount of the base used is usually in the range of 1 to 10 times the molar amount of the compound represented by general formula (2).

[0045] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include inert solvents such as linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, tetrahydrofuran, etc.; nitriles such as acetonitrile and propionitrile; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, etc.; and alcohols such as methanol, ethanol, propanol, butanol, 2-propanol, etc. These inert solvents can be used alone or in combination. The amount used can be selected appropriately from the range of 0.1 to 100 L per mole of the compound represented by general formula (2).

[0046] Since this reaction is an equimolar reaction, each compound may be used in equimolar amounts, although either compound may be used in excess. The reaction temperature in this reaction is typically within the range of about 0°C to the boiling point of the solvent used. The reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is typically selected appropriately within the range of several minutes to 48 hours. After completion of the reaction, the target product can be isolated from the reaction system containing the target product by conventional methods, and can be produced by purifying it, if necessary, by recrystallization, column chromatography, or the like.

[0047] Production Method 2 The compound of the present invention represented by the general formula (1-2) can be produced from the compound of the general formula (2) by the following step [b].

[0048] {In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , Q and Y are the same as above. L represents a leaving group such as chlorine, bromine, an imidazolyl group, or a trichloromethoxy group.}

[0049] Production Method of Step [b] The compound represented by general formula (1-2) can be produced by reacting the compound represented by general formula (2) with a reaction product of the compound represented by general formula (4) and the compound represented by general formula (5) in the presence or absence of an inert solvent and a base.

[0050] Examples of the base that can be used in this reaction include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; carbonates such as lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, calcium carbonate, magnesium carbonate, and cesium carbonate; acetates such as lithium acetate, sodium acetate, and potassium acetate; and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, N,N-diisopropylethylamine, and DBU, and the amount used is usually in the range of 1 to 10 times the molar amount of the compound represented by general formula (2).

[0051] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include inert solvents such as linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, tetrahydrofuran, etc.; nitriles such as acetonitrile and propionitrile; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, etc.; and alcohols such as methanol, ethanol, propanol, butanol, 2-propanol, etc. These inert solvents can be used alone or in combination. The amount used can be selected appropriately from the range of 0.1 to 100 L per mole of the compound represented by general formula (2).

[0052] Since this reaction is an equimolar reaction, each compound may be used in equimolar amounts, although either compound may be used in excess. The reaction temperature in this reaction is typically within the range of about 0°C to the boiling point of the solvent used. The reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is typically selected appropriately within the range of several minutes to 48 hours. After completion of the reaction, the target product can be isolated from the reaction system containing the target product by conventional methods, and can be produced by purifying it, if necessary, by recrystallization, column chromatography, or the like.

[0053] Method for producing starting material 1 Among the compounds represented by general formula (2) that are starting materials, R 1 , R 2 and R 3 The compound in which is a hydrogen atom can be produced by the method described in WO 2008 / 014311 or a method analogous thereto.

[0054] Method for producing starting material 2 Among the compounds represented by general formula (2) that are starting materials, R 2 and R 3 The compound (2-1) in which is other than a hydrogen atom can be produced by the following production method, that is, from a compound represented by general formula (6) by the following steps [c] and [d].

[0055] {In the formula, R 1 and Q are the same as above. 2' and R 3' represents a (C1-C6) alkyl group, a (C1-C6) alkoxy(C1-C6) alkyl group, an N-(C1-C6) alkylamino(C1-C6) alkyl group, a (C1-C6) alkoxycarbonylamino(C1-C6) alkyl group, or a phenyl group, and may be the same or different. R 2' and R 3' may be bonded to each other to form a 3- to 7-membered ring. R' represents, for example, a (C1-C6) alkyl group such as a methyl group or an ethyl group.

[0056] Production Method of Step [c] A compound represented by general formula (8) can be produced by reacting a compound represented by general formula (6) with a compound represented by general formula (7) in the presence of a base and an inert solvent.

[0057] Examples of the base that can be used in this reaction include alkyllithiums such as methyllithium, normal butyllithium, secondary butyllithium, and tertiary butyllithium; organometallic compounds such as lithium diisopropylamide, lithium hexamethyldisilazane, and sodium hexamethyldisilazane; alkoxides such as sodium methoxide, sodium ethoxide, sodium tertiary butoxide, and potassium tertiary butoxide; and metal hydrides such as sodium hydride and potassium hydride. The amount of the base used is usually in the range of 1 to 10 times the molar amount of the compound represented by general formula (6).

[0058] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include inert solvents such as linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc.; linear or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran, etc.; nitriles such as acetonitrile, propionitrile, etc.; esters such as methyl acetate, etc.; ketones such as acetone, methyl ethyl ketone, etc.; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, etc.; and alcohols such as methanol, ethanol, propanol, butanol, 2-propanol, etc. These inert solvents can be used alone or in combination. The amount used may be appropriately selected from the range of usually 0.1 to 100 L per mole of the compound represented by the general formula (6).

[0059] Since this reaction is an equimolar reaction, it is sufficient to use equimolar amounts of each compound, but it is also possible to use an excess of one compound. The reaction temperature in this reaction is typically within the range of -100°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is typically selected appropriately within the range of several minutes to 48 hours. After completion of the reaction, the target product can be isolated from the reaction system containing the target product by conventional methods, and can be produced by purifying it by recrystallization, column chromatography, etc., as necessary. Alternatively, the target product can be subjected to the next step without isolation.

[0060] Preparation Method of Step [d] A compound represented by general formula (2-1) can be prepared by subjecting a compound represented by general formula (8) to a cyclization reaction in the presence of a base and an inert solvent.

[0061] Examples of the base that can be used in this reaction include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; carbonates such as lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, calcium carbonate, and magnesium carbonate; acetates such as lithium acetate, sodium acetate, and potassium acetate; and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, and N,N-diisopropylethylamine, and the like. The amount of the base used is usually in the range of 1 to 10 times the molar amount of the compound represented by general formula (8).

[0062] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include inert solvents such as linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, tetrahydrofuran, etc.; nitriles such as acetonitrile and propionitrile; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, etc.; and alcohols such as methanol, ethanol, propanol, butanol, 2-propanol, etc. These inert solvents can be used alone or in combination. The amount used can be selected appropriately from the range of 0.1 to 100 L per mole of the compound represented by general formula (8).

[0063] The reaction temperature in this reaction may generally be in the range of about 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may generally be selected appropriately in the range of several minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and can be produced by purifying it, if necessary, by recrystallization, column chromatography, etc. Alternatively, the target product may be subjected to the next step without isolation.

[0064] Next, specific examples of the compound of the present invention are shown below. In the table below, Me represents a methyl group, Et represents an ethyl group, i-Pr represents an isopropyl group, i-Bu represents an isobutyl group, c-Pr represents a cyclopropyl group, c-Hex represents a cyclohexyl group, Ph represents a phenyl group, Bn represents a benzyl group, and Boc represents a tertiary butoxycarbonyl group. The dots in the structural formula indicate the bond position. Physical properties are expressed as melting point (°C) or H 1 -NMR is shown. 1 -NMR data are shown in Table 4.

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076] Pest control agents containing the compound represented by general formula (1) of the present invention or a salt thereof as an active ingredient can be used as agricultural and horticultural pest control agents, animal ectoparasite control agents, and animal endoparasite control agents. As agricultural and horticultural pest control agents, they can be used to control various agricultural and forestry pests, horticultural pests, and stored grain pests, sanitary pests, and nematodes that attack rice, fruit trees, vegetables, other crops, and ornamental plants. Furthermore, pest control agents containing the compound represented by general formula (1) of the present invention or a salt thereof as an active ingredient have excellent environmental safety, such as physical properties suitable for various labor-saving application methods, systemic activity, and appropriate soil persistence. Furthermore, pest control agents containing the compound represented by general formula (1) of the present invention or a salt thereof as an active ingredient have little impact on natural enemies, beneficial insects such as European honeybees and bumblebees, and environmental organisms such as midges.

[0077] Examples of the above-mentioned pests or nematodes include the following. Lepidoptera (Lepidoptera) pests include, for example, Parasa consocia, Anomis mesogona, Papilio xuthus, Matsumuraeses azukivora, Ostrinia scapulalis, Spodoptera exempta, Hyphantria cunea, Ostrinia furnacalis, Pseudaletia separata, Tinea translucens, Bactra furfuryla, Parnara guttata, Marasmia exigua, Sesamia inferens, potato leaf moth (Brachmia triannulella), bag moth (Monema flavescens), nettle looper moth (Trichoplusia ni), turmeric moth (Pleuroptya ruralis), plum geometries (Cystidia couaggaria), blue-striped silver butterfly (Lampides boeticus), Japanese hawk moth (Cephonodes hylas), cotton bollworm (Helicoverpa armigera), large bird moth (Phalerodonta manleyi), Japanese silk moth (Eumeta japonica), large cabbage white (Pieris brassicae), banded moth (Malacosoma neustria testacea), persimmon stalk moth (Stathmopoda masinissa), persimmon leaf moth (Cuphodes diospyrosella), and Japanese rice tortrix moth (Archips xylosteanus, turnip moth (Agrotis segetum), sugarcane moth (Tetramoera schistaceana), swallowtail butterfly (Papilio machaon hippocrates), yellow-spotted bat (Endoclyta sinensis), silver leafminer moth (Lyonetiaprunifoliella, Golden leaf moth (Phyllonorycter ringoneella), Chestnut leaf moth (Cydia kurokoi), Chestnut green fruit moth (Eucoenogenes aestuosa), Grapeberry moth (Lobesia botrana), Black-spotted green moth (Latoia sinica), Black-spotted moth (Euzophera batangensis), Mulberry leaf moth (Phalonidia mesotypa), Mulberry spotted moth (Spilosoma imparilis), Mulberry leaf moth (Glyphodes pyloalis), Mulberry leaf moth (Olethreutes mori), Brown moth (Tineola bisselliella), Bat moth (Endoclyta excrescens), Oriental rice moth (Nemapogon granellus), Little grass moth (Synanthedon hector), Codling moth (Cydia pomonella), diamondback moth (Plutella xylostella), rice leafroller (Cnaphalocrocis medinalis), southern pink borer (Sesamia calamistis), rice borer (Scirpophaga incertulas), grass moth (Pediasia teterrellus), potato tuber moth (Phthorimaea operculella), oriental horn moth (Stauropus fagi persimilis), beetle moth (Etiella zinckenella), beetle armyworm (Spodoptera exigua), white-spotted long-eared bat (Palpifer sexnotata), beetle armyworm (Spodoptera mauritia), rice leafroller (Scirpophaga innotata), white-spotted cutworm (Xestia c-nigrum), and striped armyworm (Spodoptera depravata), Ephestia kuehniella, Angerona prunaria, Clostera anastomosis, Pseudoplusiaincludens), soybean pod moth (Matsumuraeses falcana), tobacco moth (Helicoverpa assulta), silver looper moth (Autographa nigrisigna), black cutworm moth (Agrotis ipsilon), brown tussock moth (Euproctis pseudoconspersa), smaller tea tortrix moth (Adoxophyes orana), tea leaf moth (Caloptilia theivora), tea tortrix moth (Homona magnanima), spotted tea moth (Ephestia elutella), tea leaf moth (Eumeta minuscula), red-spotted orb moth (Clostera anachoreta), Japanese oak leaf moth (Heliothis maritima), Japanese burrowing moth (Sparganothis pilleriana), corn borer (Busseola fusca), tussock moth (Euproctis subflava), giant geometrid moth (Biston robustum), tomato fruitworm (Heliothis zea), white-streaked leafroller (Aedia leucomelas), pear moth (Narosoideus flavidorsalis), pear moth (Viminia rumicis), pear leaf moth (Bucculatrix pyrivorella), pear fruit moth (Grapholita molesta), pear leaf moth (Spulerina astaurota), pear moth (Ectomyelois pyrivorella), rice stem borer (Chilo suppressalis), onion leaf moth (Acrolepiopsis sapporensis), Indian meal moth (Plodia interpunctella), Japanese cereal moth (Hellula undalis), Japanese cereal moth (Sitotroga cerealella), common cutworm (Spodoptera litura), tortrix moth (Eucosma aporema), rose moth (Acleris comariana), Small black moth (Scopelodes contractus), Small white tussock moth (Orgyia thyellina), Fall armyworm (Spodopterafrugiperda, butterbur moth (Ostrinia zaguliaevi), two-banded weed moth (Naranga aenescens), two-banded false grass moth (Andraca bipunctata), grapevine clearwing moth (Paranthrene regalis), grapevine wasp (Acosmeryx castanea), grapevine leafminer moth (Phyllocnistis toparcha), grapevine tortrix moth (Endopiza viteana), grapevine narrow-leaved moth (Eupoecillia ambiguella), velvet bean caterpillar (Anticarsia gemmatalis), narrow-leaved gray moth (Cnephasia cinereipalpana), gypsy moth (Lymantria dispar), pine moth (Dendrolimus spectabilis), bean root moth (Leguminivora glycinivorella), bean leaf moth (Maruca testulalis, Bean Bean Moth (Matsumuraeses phaseoli), Bean Bean Moth (Caloptilia soyella), Citrus Leafminer (Phyllocnistis citrella), White-spotted Leafminer (Omiodes indicate), Common Green Tortrix Moth (Archips fuscocupreanus), Three-leaf Goldfinch (Acanthoplusia agnata), Bag Moth (Bambalina sp.), Peach Fruit Moth (Carposina niponensis), Peach Spotted Moth (Conogethes punctiferalis), Peach Sesiidae (Synanthedon sp.), Peach Leafminer (Lyonetia clerkella), Common Yellow Swallowtail (Papilio helenus), Common Egret Butterfly (Colias erate poliographus), Common Orca Moth (Phalera flavescens, Pieris rapae crucivora, Pieris rapae, and other white butterflies, Euproctis similis, Acrolepiopsissuzukiella, European corn borer (Ostrinia nubilalis), armyworm moth (Mamestra brassicae), mugwort geometries (Ascotis selenaria), mugwort leafroller moth (Ptheochroides clandestina), apple leafroller moth (Hoshinoa adumbratana), apple moth (Odonestis pruni japonensis), apple shriveling moth (Triaena intermedia), smaller apple tortrix moth (Adoxophyes orana fasciata), apple fruit moth (Grapholita inopinata), white apple tortrix moth (Spilonota ocellana), grey apple tortrix moth (Spilonota lechriaspis), apple leafroller moth (Illiberis pruni), apple fruit moth (Argyresthia conjugella), apple leafroller moth (Caloptilia zachrysa, Archips breviplicanus, Anomis flava, Pectinophora gossypiella, Notarcha derogata, Diaphania indica, Heliothis virescens, and Earias cupreoviridis.

[0078] Hemiptera (Hemiptera) pests include, for example, the green grass bug (Nezara antennata), the red-striped rice bug (Stenotus rubrovittatus), the red-striped rice bug (Graphosoma rubrolineatum), the red-bearded green rice bug (Trigonotylus coelestialium), the red-spotted leaf bug (Aeschynteles maculatus), the red-spotted rice bug (Creontiades pallidifer), the red-spotted rice bug (Dysdercus cingulatus), the red-spotted scale bug (Chrysomphalus ficus), the red-spotted scale bug (Aonidiella aurantii), and the brown cicada (Graptopsaltria nigrofuscata), American long-horned stink bug (Blissusleucopterus), Icerya scale bug (Icerya purchasi), striped stink bug (Piezodorus hybneri), rice stink bug (Lagynotomus elongatus), rice yellow leafhopper (Thaia subrufa), black rice stink bug (Scotinophara lurida), thorny long-horned aphid (Sitobion ibarae), Iwasaki stink bug (Stariodes iwasakii), pale-stained scale (Aspidiotus destructor), pale-stained green rice bug (Taylorilygus pallidulus), plum horn aphid (Myzusmumecola), plum white scale (Pseudaulacaspis prunicola), pea aphid (Acyrthosiphon pisum), spider bug (Anacanthocoris striicornis), large black-spotted stink bug (Ectometopterus micantulus), large spur-spotted spotted stink bug (Eysarcoris lewisi), large leaf bug (Molipteryx fuliginosa), Japanese giant leafhopper (Cicadella viridis), red-veined aphid (Rhopalosophumrufiabdominalis), olive scale (Saissetia oleate), greenhouse whitefly (Trialeurodes vaporariorum), oak leafhopper (Aguriahana quercus), mirid bugs (Lygus spp.), Japanese citrus aphid (Euceraphis punctipennis), citrus scale (Andaspis kashicola), citrus scale (Coccus pseudomagnoliarum), oak leafbug (Cavelerius saccharivorus), chrysanthemum long-horned aphid (Galeatus spinifrons), chrysanthemum long-horned aphid (Macrosiphoniella sanborni), yellow scale (Aonidiella citrina), brown marmorated stink bug (Halyomorpha mista), Japanese oak leafbug (Stephanitis fasciicarina), Japanese psyllid (Trioza camphorae), spider bug (Leptocorisa chinensis), chestnut psyllid (Trioza quercicola), walnut earworm (Uhlerites latius), grape leafhopper (Erythroneura comes), black-legged stink bug (Paromius exiguus), black rice scale (Duplaspidiotus claviger), black-striped leafhopper (Nephotettix nigropictus), black-spotted rice turtle (Halticiellus insularis), black planthopper (Perkinsiella saccharicida), black apple psyllid (Psylla malivorella), mulberry psyllid (Anomomeura mori), mulberry mealybug (Pseudococcus longispinis), Mulberry scale (Pseudaulacaspis pentagona), Mulberry cotton scale (Pulvinaria kuwacola), Red-spotted grass bug (Apolygus lucorum), Togo gourd long-legged bughemipterus), Phyllostomum aphid (Toxoptera aurantii), sugarcane mealybug (Saccharicoccus sacchari), sugarcane aphid (Geoica lucifuga), sugarcane brown planthopper (Numata muiri), San Jose scale (Comstockaspis perniciosa), citrus snow scale (Unaspis citri), potato aphid (Aulacorthum solani), white spotted stink bug (Eysarcoris ventralis), silverleaf whitefly (Bemisia argentifolii), white leafhopper (Cicadella spectra), white-spotted scale (Aspidiotus hederae), white-spotted stink bug (Liorhyssus hyalinus), white-backed psyllid (Calophya nigridorsalis), white-backed planthopper (Sogatella furcifera), broad bean aphid (Megoura crassicauda), radish aphid (Brevicoryne brassicae), soybean aphid (Aphis glycines), Taiwan spider bug (Leptocorisa oratorius), Taiwan green leafhopper (Nephotettix virescens), Taiwan long-horned aphid (Uroeucon formosanum), tobacco leaf bug (Cyrtopeltis tennuis), tobacco whitefly (Bemisia tabaci), tea stubble scale (Lecanium persicae), black tea spot scale (Parlatoria theae), tea leaf scale (Pseudaonidia paeoniae), tea green leafhopper (Empoasca onukii), brown-winged green bug (Plautia stali), tulip root aphid (Dysaphis tulipae), tulip long-horned aphid (Macrosiphum euphorbiae), azalea leafhoppers (Stephanitis pyrioides), and hornworms (Ceroplastesceriferus), Camellia black spotted scale (Parlatoria camelliae), Green rice bug (Apolygus spinolai), Green rice leafhopper (Nephotettix cincticeps), Shiny green stink bug (Glaucias subpunctatus), Sugar beet rice bug (Orthotylus flavosparsus), Corn aphid (Rhopalosiphum maidis), Corn planthopper (Peregrinus maidis), Spiny spotted stink bug (Eysarcoris parvus), Bed bug (Cimex lectularius), Brown planthopper (Psylla abieti), Brown planthopper (Nilaparvata lugens), Pittosporum psylla (Psylla tobirae), Long-legged bug (Eurydema rugosum), Pear aphid (Schizaphis piricola), pear psylla (Psylla pyricola), pear spotted scale (Parlatoreopsis pyri), pear earworm (Stephanitis nashi), pear mealybug (Dysmicoccus wistariae), white pear scale (Lepholeucaspis japonica), pear aphid (Sappaphis piri), false radish aphid (Lipaphis erysimi), onion aphid (Neotoxoptera formosana), husk aphid (Rhopalosophum nymphaeae), rose leafhopper (Edwardsianarosae), Japanese long-legged scale (Pinnaspisaspidistrae), alder psylla (Psylla alni), alder leafhopper (Speusotettix subfusculus), alder leafhopper (Alnetoidia alneti), brown planthopper (Sogatella panicicola), long-horned rice bug (Adelphocoris lineolatus), small red spotted stink bug (Dysdercus poecilus), small black scale (Parlatoria ziziphi), small earworm (Uhleritesdebile), small brown planthopper (Laodelphax striatellus), small long-legged bug (Eurydema pulchrum), small stink bug (Cletus trigonus), small long-legged stink bug (Clovia punctata), small leafhoppers (Empoasca sp.), flat-headed scale (Coccus hesperidum), flat-headed long-legged bug (Pachybrachius luridus), wisteria mealybug (Planococcus kraunhiae), two-striped rice bug (Stenotus binotatus), small rice-striped leafhopper (Arboridia apicalis), rice-striped leafhopper (Macrosteles fascifrons), spotted stink bug (Dolycoris baccarum), spotted black rice bug (Adelphocoris triannulatus), grape aphid (Viteus vitifolii), ground cherry bug (Acanthocoris sordidus), narrow-legged stink bug (Leptocorisa acuta), narrow-legged long-legged bug (Macropes obnubilus), narrow-legged stink bug (Cletus punctiger), narrow-legged stink bug (Riptortus clavatus), potato piscid (Paratrioza cockerelli), Japanese oak leafhopper (Aphrophora costalis), Japanese spotted grasshopper (Lygus disponsi), spotted rice bug (Lygus saundersi), pine mealybug (Crisicoccus pini), pine leafhopper (Empoasca abietis), Matsumoto mealybug (Crisicoccus matsumotoi), bean aphid (Aphis craccivora), the spotted stink bug (Megacopta punctatissimum), the spotted stink bug (Eysarcoris guttiger), the citrus persimmon scale (Lepidosaphes beckii), the citrus psyllid (Diaphorina citri), the citrus black aphid (Toxoptera citricidus), the citrus mealybug (Planococcuscitri), citrus whitefly (Dialeurodes citri), citrus spine whitefly (Aleurocanthus spiniferus), citrus mealybug (Pseudococcus citriculus), citrus leafhopper (Zyginella citri), citrus cotton scale (Pulvinaria citricola), citrus placode scale (Coccus discrepans), citrus round scale (Pseudaonidia duplex), citrus cotton scale (Pulvinaria aurantii), dogwood scale (Lecanium corni), southern green stink bug (Nezara viridula), wheat leaf bug (Stenodema calcaratum), wheat neck aphid (Rhopalosiphum padi), wheat long-horn aphid (Sitobion akebiae), wheat green aphid (Schizaphis graminum), wheat leafhopper (Sorhoanus tritici), straw corn aphid (Brachycaudus helichrysi), purple stink bug (Carpocoris purpureipennis), peach aphid (Myzus persicae), peach butterbur aphid (Hyalopterus pruni), willow aphid (Aphis farinose yanagicola), willow earworm (Metasalis populi), Yanon scale (Unaspis yanonensis), mountain psylla (Mesohomotoma camphorae), snow willow aphid (Aphis spiraecola), apple aphid (Aphis pomi), apple persimmon scale (Lepidosaphes ulmi), Apple psylla (Psylla mali), Black apple leafhopper (Heterocordylus flavipes), Apple horn aphid (Myzus malisuctus), Apple leafhopper (Aphidonuguis mali), Apple leafhopper (Orientus ishidai), Apple fly aphid (Ovatusmalicolens), apple aphid (Eriosoma lanigerum), ruby ​​wax moth (Ceroplastes rubens), and cotton aphid (Aphis gossypii).

[0079] Examples of pests that belong to the order Coleoptera include the Japanese longhorn beetle (Xystrocera globosa), the green leaf beetle (Paederus fuscipes), the green leaf beetle (Eucetonia roelofsi), the azuki bean weevil (Callosobruchus chinensis), the sweet potato weevil (Cylas formicarius), the alfalfa weevil (Hypera postica), the rice weevil (Echinocnemus squameus), the rice leaf beetle (Oulema oryzae), the rice root beetle (Donacia provosti), the rice water weevil (Lissorhoptrus oryzophilus), the potato leaf beetle (Colasposoma dauricum), the potato weevil (Euscepes postfasciatus), and the common ladybird beetle (Epilachna varivestis), kidney bean weevil (Acanthoscelides obtectus), western corn rootworm (Diabrotica virgifera virgifera), plum vest weevil (Involvulus cupreus), cucumber leaf beetle (Aulacophora femoralis), pea weevil (Bruchus pisorum), large 24-spotted ladybird beetle (Epilachna vigintioctomaculata), oak leaf beetle (Carpophilus dimidiatus), tortoise leaf beetle (Cassida nebulosa), yellow-legged flea beetle (Luperomorpha tunebrosa), striped flea beetle (Phyllotreta striolata), yellow-spotted longhorn beetle (Psacothea hilaris), yellow-spotted longhorn beetle (Aeolesthes chrysothrix), chestnut weevil (Curculio sikkimensis), chestnut beetle (Carpophilus hemipterus), flower beetle (Oxycetonia jucunda), corn rootworms (Diabrotica spp.), scarab beetle (Mimela splendens), rice weevil (Sitophilus zeamais), red flour beetle (Tribolium castaneum), rice weevil (Sitophilus oryzae), lesser red flour beetle (Palorus subdepressus), cockchafer beetle (Melolontha japonica), spotted longhorn beetle (Anoplophora malasiaca), mealworm beetle (Neatus picipes), Colorado potato beetle (Leptinotarsa ​​decemlineata), southern corn rootworm (Diabrotica undecimpunctata howardi), grass weevil (Sphenophorus venatus), four-spotted long-necked beetle (Crioceris quatuordecimpunctata), plum curculion (Conotrachelus nenuphar, radish weevil (Ceuthorhynchidius albosuturalis), radish leaf beetle (Phaedon brassicae), cigarette beetle (Lasioderma serricorne), small corn weevil (Sitona japonicus), brown dung beetle (Adoretus tenuimaculatus), brown mealworm beetle (Tenebrio molitor), brown dung beetle (Basilepta balyi), nail weevil (Hypera nigrirostris), tentacle leaf beetle (Chaetocnema concinna), cuprea beetle (Anomala cuprea), long-legged scarab beetle (Heptophylla picea), 24-spotted ladybird beetle (Epilachna vigintioctopunctata), northern corn rootworm (Diabrotica longicornis), flower chafer (Eucetonia pilifera), wireworms (Agriotes spp.), lesser cutworm beetle (Attagenus unicolor japonicus), lesser yellow-winged monkey beetle (Pagria signata), lesser Japanese scarab beetle (Anomala rufocuprea), lesser red flour beetle (Palorus ratzeburgii), lesser mealworm beetle (Alphitobius laevigatus), lesser round cutworm beetle (Anthrenus verbasci), flat-headed wood borer (Lyctus brunneus), flat-headed red flour beetle (Tribolium confusum), lesser two-striped leaf beetle (Medythia nigrobilineata), grape tiger longhorn beetle (Xylotrechus pyrrhoderus), potato leaf beetle (Epitrix cucumeris), pine bark beetle (Tomicus piniperda), Japanese pine longhorn beetle (Monochamus alternatus), Japanese beetle (Popillia japonica), bean tiger beetle (Epicauta gorhami), maize weevil (Sitophilus zeamais), peach vest weevil (Rhynchites heros), vegetable weevil (Listroderes costirostris), cowpea weevil (Callosobruchus maculatus), apple weevil (Phyllobius armatus), apple blossom weevil (Anthonomus pomorum), blue leaf beetle (Linaeidea aenea), and boll weevil (Anthonomus grandis).

[0080] Examples of Diptera (Flying) pests include Culex pipiens pallens, Pegomya hyoscyami, Liriomyza huidobrensis, Musca domestica, Chlorops oryzae, Hydrellia sasakii, Agromyza oryzae, Hydrellia griseola, Ophiomyia phaseoli, Dacus cucurbitae, Drosophila suzukii, Rhacochlaena suzukii, and Rhacochlaena ulmeri. japonica), the giant house fly (Muscina stabulans), the giant horn fly (Megaselia spiracularis), and other flea flies, the Japanese house fly (Clogmia albipunctata), the Japanese crane fly (Tipula aino), the Japanese black blowfly (Phormia regina), the small Asian mosquito (Culex tritaeniorhynchus), the Chinese anopheles mosquito (Anopheles sinensis), the root fly (Hylemya brassicae), and the soybean pod gall midge (Asphondylia sp.), seed fly (Delia platura), onion fly (Delia antiqua), European cherry fruit fly (Rhagoletis cerasi), Culex pipiens molestus Forskal, Mediterranean fruit fly (Ceratitis capitata), Sciarid gnat (Bradysia agrestis), beet root fly (Pegomya cunicularia), tomato leafminer (Liriomyza sativae), eggplant leafminer (Liriomyza bryoniae), ground miner (Chromatomyia horticola), onion leafminer (Liriomyza chinensis), Southern house mosquito (Culex quinquefasciatus), Aedes aegypti, Aedes albopictus, pea leafminer (Liriomyza trifolii, tomato leafminer (Liriomyza sativae), oriental fruit fly (Dacus dorsalis), citrus fly (Dacus tsuneonis), wheat gall midge (Sitodiplosis mosellana), wheat stem miner (Meromuza nigriventris), Mexican fruit fly (Anastrepha ludens), and apple fly (Rhagoletis pomonella).

[0081] Examples of Hymenoptera (Hymenoptera) pests include Pristomyrmex pungens, ant wasps, Monomorium pharaohnis, Pheidole noda, Athalia rosae, chestnut gall wasp (Dryocosmus kuriphilus), black mountain ant (Formica fusca japonica), hornets, Athalia infumata infumata, Arge pagana, Athalia japonica, leaf-cutter ants (Acromyrmex spp.), fire ants (Solenopsis spp.), apple sawflies (Arge mali), and orange ants (Ochetellus glaber).

[0082] Examples of Orthoptera (Orthoptera) pests include the Japanese grasshopper (Homorocoryphus lineosus), the mole cricket (Gryllotalpa sp.), the Japanese carp locust (Oxya hyla intricata), the rice grasshopper (Oxya yezoensis), the Japanese migratoria locust (Locusta migratoria), the long-winged grasshopper (Oxya japonica), the Japanese grasshopper (Homorocoryphus jezoensis), and the field cricket (Teleogryllus emma).

[0083] Examples of Thripida pests include red banded thrips (Selenothrips rubrocinctus), rice thrips (Stenchaetothrips biformis), rice thrips (Haplothrips aculeatus), rice thrips (Ponticulothrips diospyrosi), yellow flower thrips (Thrips flavus), green leaf thrips (Anaphothrips obscurus), cusk thrips (Liothrips floridensis), gladiolus thrips (Thrips simplex), black flower thrips (Thrips nigropilosus), croton thrips (Heliothrips haemorrhoidalis), and mulberry thrips (Pseudodendrothrips mori), Cosmos thrips (Microcephalothrips abdominalis), Brown weasel thrips (Leeuwenia pasanii), Brown weasel thrips (Litotetothrips pasaniae), Citrus thrips (Scirtothrips citri), Chinese weasel thrips (Haplothrips chinensis), Soybean thrips (Mycterothrips glycines), Soybean light brown thrips (Thrips setosus), Tea leaf thrips (Scirtothrips dorsalis), Tea black thrips (Dendrothrips minowai), Japanese claw thrips (Haplothrips niger), Onion thrips (Thrips tabaci), Black onion thrips (Thrips alliorum), flower thrips (Thrips hawaiiensis), flower thrips (Haplothrips kurdjumovi), hair thrips (Chirothrips manicatus), plain flower thrips (Frankliniella intonsa), loquat flower thrips (Thrips coloratus), western flower thrips (Franklinella occidentalis), southern flower thrips (Thripspalmi), Frankliniella lilivora, and Liothrips vaneeckei.

[0084] Examples of pests of the order Acarina include ticks such as the green chigger (Leptotrombidium akamushi), the red-legged spider mite (Tetranychus ludeni), the American dog tick (Dermacentor variabilis), the stone spider mite (Tetranychus truncatus), the house dust mite (Ornithonyssus bacoti), the dog mite (Demodex canis), the cherry spider mite (Tetranychus viennensis), the Kanzawa spider mite (Tetranychus kanzawai), and the brown dog tick (Rhipicephalus sanguineus); ticks such as the stag beetle mite (Cheyletus malaccensis), the long-legged dust mite (Tyrophagus putrescentiae), the house dust mite (Dermatophagoides farinae), and the redback spider (Latrodectus hasseltii, Taiwanese Dermacentor mite (Dermacentor taiwanicus), Tea long rust mite (Acaphylla theavagrans), Tea dust mite (Polyphagotarsonemus latus), Tomato rust mite (Aculops lycopersici), Fowl mite (Ornithonyssus sylvairum), Two-spotted spider mite (Tetranychus urticae), False pear rust mite (Eriophyes chibaensis), Scabiei mite (Sarcoptes scabiei), Long-spined tick (Haemaphysalis longicornis), Black-legged tick (Ixodes scapularis), Spinach long-spined mite (Tyrophagus similis), Cheyletus eruditus, Citrus red mite (Panonychus citri), Cheyletus moorei), Southern spider mite (Brevipalpus phoenicis), Ear mite (Octodectes cynotis), Dermatophagoides ptrenyssnus, Haemaphysalis flava, Ixodes ovatusovatus), Ryukyu citrus rust mite (Phyllocoptruta citri), apple rust mite (Aculus schlechtendali), apple red mite (Panonychus ulmi), lone star tick (Amblyomma americanum), and red mite (Dermanyssus gallinae), Robin bulb mite (Rhyzoglyphus robini), and a species of bulb mite (Sancassania sp.).

[0085] Examples of termite pests include the Amami termite (Reticulitermes miyatakei), the American dry wood termite (Incisitermes minor), the Formosan termite (Coptotermes formosanus), the Japanese termite (Hodotermopsis japonica), the Formosan termite (Reticulitermes sp.), the Japanese red-legged termite (Reticulitermes flaviceps amamianus), the Japanese staghorn termite (Glyptotermes kushimensis), the Formosan termite (Coptotermes guangzhoensis), the Japanese staghorn termite (Neotermes koshunensis), the Japanese staghorn termite (Glyptotermes kodamai), the Satsuma termite (Glyptotermes satsumensis), the Japanese staghorn termite (Cryptotermes domesticus), and the Taiwan termite (Odontotermes formosanus), Glyptotermes nakajimai, Pericapritermes nitobei, and Reticulitermes speratus.

[0086] Examples of cockroach pests include the Smoky brown cockroach (Periplaneta fuliginosa), the German cockroach (Blattella germanica), the Asian cockroach (Blatta orientalis), the Brown cockroach (Periplaneta brunnea), the lesser German cockroach (Blattella lituricollis), the Japanese cockroach (Periplaneta japonica), and the American cockroach (Periplaneta americana).

[0087] Examples of nematodes include the strawberry root nematode (Nothotylenchus acris), the rice root nematode (Aphelenchoides besseyi), the northern root-knot nematode (Pratylenchus penetrans), the northern root-knot nematode (Meloidogyne hapla), the sweet potato root-knot nematode (Meloidogyne incognita), the potato cyst nematode (Globodera rostochiensis), the Java root-knot nematode (Meloidogyne javanica), the soybean cyst nematode (Heterodera glycines), the southern root-leakage nematode (Pratylenchus coffeae), the wheat root-leakage nematode (Pratylenchus neglectus), and the citrus root nematode (Tylenchus semipenetrans).

[0088] Examples of mollusks include apple snails (Pomacea canaliculata), African snails (Achatina fulica), slugs (Meghimatium bilineatum), brown slugs (Lehmannina valentiana), red slugs (Limax flavus), and the light blue snail (Acusta despecta sieboldiana).

[0089] The agricultural and horticultural pest control agent of the present invention also has a strong insecticidal effect against another pest, the tomato osmosis moth (Tuta absoluta).

[0090] The agricultural and horticultural pest control agent of the present invention, which contains the compound represented by formula (1) or a salt thereof as an active ingredient, has a remarkable control effect against pests that cause damage to paddy field crops, field crops, fruit trees, vegetables, other crops, and flowers, etc., and therefore the expected effect of the agricultural and horticultural pest control agent of the present invention can be achieved by treating it with a cultivation carrier such as a seedling facility, paddy field, field, seeds of fruit trees, vegetables, other crops, flowers, etc., paddy water, stems and leaves, or soil, etc., in accordance with the time when pest emergence is predicted or at the time when pest emergence is confirmed. Among these, a preferred application form is application utilizing so-called systemic translocation, in which the compound of the present invention is applied to seedling soil for crops, flowers, etc., soil in planting holes at the time of transplanting, base of plants, irrigation water, cultivation water in hydroponic cultivation, etc., and is absorbed by the roots with or without soil.

[0091] Useful plants for which the agricultural and horticultural pest control agent of the present invention can be used are not particularly limited, and examples thereof include cereals (e.g., rice, barley, wheat, rye, oats, corn, etc.), beans (soybeans, adzuki beans, broad beans, peas, kidney beans, peanuts, etc.), fruit trees and fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherries, walnuts, chestnuts, almonds, bananas, etc.), leafy vegetables (cabbage, tomato, spinach, broccoli, lettuce, onion, leeks (chives, scallions), bell peppers, eggplant, strawberries, peppers, okra, chives, etc.), root vegetables (carrots, potatoes, sweet potatoes, taro, daikon radish, turnips, lotus root, burdock, garlic, onions, etc.), and the like. Examples of plants that can be used include: crops for processing (cotton, hemp, beets, hops, sugarcane, sugar beets, olives, rubber, coffee, tobacco, tea, etc.), melons (pumpkin, cucumber, watermelon, Sakhalin gourd, melon, etc.), pasture grasses (orchard grass, sorghum, timothy, clover, alfalfa, etc.), turfgrass (Korean grass, bentgrass, etc.), ornamental crops for perfumes and the like (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), flowers (chrysanthemum, rose, carnation, orchid, tulip, lily, etc.), garden trees (ginkgo, cherry trees, Japanese maple, etc.), and forest trees (abies firs, spruces, pines, hiba, cedar, cypress, eucalyptus, etc.).

[0092] The above-mentioned "plant" also includes plants to which tolerance has been imparted by classical breeding methods or genetic engineering techniques to HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, acetyl-CoA carboxylase inhibitors such as sethoxydim, and herbicides such as bromoxynil, dicamba and 2,4-D.

[0093] Examples of "plants" that have been given tolerance through classical breeding methods include rapeseed, wheat, sunflower, and rice that are resistant to imidazolinone ALS-inhibiting herbicides such as imazethapyr, which are already sold under the trade name Clearfield (registered trademark). Similarly, soybeans that have been given tolerance to sulfonylurea ALS-inhibiting herbicides such as thifensulfuron methyl through classical breeding methods are already sold under the trade name STS soybeans. Similarly, examples of plants that have been given tolerance to acetyl-CoA carboxylase inhibitors such as trione oxime and aryloxyphenoxypropionic acid herbicides through classical breeding methods include SR corn. Plants to which resistance to acetyl-CoA carboxylase inhibitors has been imparted are described in Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA), Vol. 87, pp. 7175-7179 (1990), and elsewhere. Furthermore, mutant acetyl-CoA carboxylases resistant to acetyl-CoA carboxylase inhibitors have been reported in Weed Science, Vol. 53, pp. 728-746 (2005), and plants resistant to acetyl-CoA carboxylase inhibitors can be produced by introducing such mutant acetyl-CoA carboxylase genes into plants by genetic engineering techniques or by introducing a mutation related to conferring resistance into plant acetyl-CoA carboxylase. Furthermore, chimeraplasty techniques (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: By introducing a nucleic acid with a base substitution mutation, such as those represented by the following (see, for example, the references 316-318), into a plant cell to introduce a site-specific amino acid substitution mutation into the plant's acetyl-CoA carboxylase gene, ALS gene, or the like, it is possible to produce plants that are resistant to acetyl-CoA carboxylase inhibitors, ALS inhibitors, or the like, and the agricultural and horticultural pest control agent of the present invention can also be used on these plants.

[0094] Further examples of toxins that can be expressed in genetically modified plants include insecticidal proteins derived from Bacillus cereus or Bacillus popiliae; δ-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C derived from Bacillus thuringiensis, insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins derived from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, wasp toxins or insect-specific neurotoxins; fungal toxins; plant lectins; agglutinins; trypsin inhibitors, serine protease inhibitors, patatin, cystatin. , papain inhibitors and the like; ribosome-inactivating proteins (RIPs) such as ricin, corn-RIP, abrin, rufin, saporin, bryodin and the like; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, cholesterol oxidase and the like; ecdysone inhibitors; HMG-CoA reductase; ion channel inhibitors such as sodium channel and calcium channel inhibitors; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; glucanase and the like.

[0095] Toxins expressed in such genetically modified plants also include hybrid toxins, truncated toxins, and modified toxins of δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab, or Cry35Ab, and insecticidal proteins such as VIP1, VIP2, VIP3, or VIP3A. Hybrid toxins are produced using recombinant technology by combining different domains of these proteins in new ways. A known example of a truncated toxin is Cry1Ab, which lacks a portion of its amino acid sequence. Modified toxins have one or more amino acids substituted in the native toxin. Examples of these toxins and recombinant plants capable of synthesizing them are described in EP-A-0 374 753, WO 93 / 07278, WO 95 / 34656, EP-A-0 427 529, EP-A-451 878, WO 03 / 052073, etc.

[0096] The toxins contained in these recombinant plants confer resistance to Coleoptera, Hemiptera, Diptera, Lepidoptera, and nematodes, among others. The agricultural and horticultural pest control agent of the present invention can be used in combination with or as a systematized combination of these technologies.

[0097] The agricultural and horticultural pest control agent of the present invention may be applied to plants where the occurrence of pests or nematodes is predicted, either as is or after appropriate dilution or suspension with water, in an amount effective for controlling the pests or nematodes. For example, for pests and nematodes occurring in fruit trees, grains, vegetables, etc., the agent may be sprayed on the stems and leaves, or may be used by soaking seeds in the agent, seed dressing, seed treatment such as calper treatment, incorporation into the entire soil layer, row application, incorporation into bed soil, treatment with cell seedlings, treatment in planting holes, treatment at the base of plants, top dressing, treatment in rice boxes, application on the water surface, or by application to soil, etc. and absorption by the roots. In addition, the agent may be applied to nutrient solutions in nutrient solution (hydroponic) cultivation, or by fumigation or trunk injection. Furthermore, the agricultural and horticultural pest control agent of the present invention may be used in an amount effective for pest control in a location where the occurrence of the pest is predicted, either as is or after appropriate dilution or suspension with water, etc., and may be sprayed against, for example, grain pests, house pests, sanitary pests, forest pests, etc., or may be applied to building materials for housing, smoked, used as bait, etc.

[0098] Seed treatment methods include, for example, a method in which seeds are soaked in a liquid or solid formulation, diluted or undiluted, to allow the agent to penetrate the seeds, a method in which a solid or liquid formulation is mixed with seeds and coated onto the seed surface, a method in which the formulation is mixed with an adhesive carrier such as a resin or polymer and then coated onto the seeds, a method in which the formulation is sprayed around the seeds at the same time as planting, etc. The "seeds" to be treated with this seed treatment refer to plant bodies in the early stages of cultivation used for plant propagation, and include, in addition to seeds, bulbs, tubers, seed potatoes, sprouts, bulbils, bulbs, or plant bodies for vegetative propagation for cutting cultivation. When carrying out the method of use of the present invention, the term "soil" or "cultivation carrier" for plants refers to a support for cultivating crops, particularly a support for growing roots. The material is not particularly limited as long as it is a material on which plants can grow, and may be so-called soil, a seedling mat, water, etc., and specific materials may be, for example, sand, pumice, vermiculite, diatomaceous earth, agar, a gel-like substance, a polymeric substance, rock wool, glass wool, wood chips, bark, etc.

[0099] Examples of methods for spraying on crop foliage or grain storage pests, house pests, sanitary pests, forest pests, etc. include a method of appropriately diluting a liquid formulation such as an emulsifiable concentrate or flowable concentrate, or a solid formulation such as a wettable powder or water dispersible granules with water and spraying it, a method of spraying a dust, fumigation, etc. Examples of methods for application to soil include a method of applying a liquid formulation, with or without dilution, to the base of plants or a seedling bed for raising seedlings, etc., a method of spraying a granule to the base of plants or a seedling bed for raising seedlings, a method of spraying a dust, wettable powder, water dispersible granules, granules, etc. and mixing it with the entire soil before sowing or transplanting, and a method of spraying a dust, wettable powder, water dispersible granules, granules, etc. in planting holes, row crops, etc. before sowing or planting plants, etc.

[0100] For application to rice seedling boxes, the formulation may vary depending on the application time, such as application at sowing, during the greening period, or at transplanting, but may be in the form of a dust, water dispersible granule, or granule. Application can also be by mixing with the soil, such as mixing the soil with a dust, water dispersible granule, or granule, for example, by mixing with the bed soil, covering the soil, or by mixing with the entire soil. Alternatively, the soil and various formulations may simply be layered alternately and applied. For application to paddy fields, solid formulations such as jumbo formulations, pack formulations, granules, and water dispersible granules, or liquid formulations such as flowables and emulsifiable concentrates, are typically sprayed onto flooded paddy fields. Additionally, at the time of rice planting, appropriate formulations can be sprayed or injected directly or mixed with fertilizer and applied to the soil. Furthermore, by using emulsions, flowables, or other liquids at the source of water flow into the paddy, such as water inlets or irrigation systems, application can be labor-saving in conjunction with the water supply.

[0101] In field crops, the agent can be applied to seeds or to cultivation carriers adjacent to the plants during the sowing to seedling raising period. For plants sown directly in fields, direct application to seeds or application to the base of plants during cultivation is preferred. Spraying treatment using granules or dredging treatment in liquid form with or without dilution in water is possible. Mixing the granules with the cultivation carrier before sowing and then sowing is also a preferred treatment. For treatment of cultivated plants to be transplanted during the sowing and seedling raising period, direct application to seeds is preferred, as well as dredging treatment of a liquid agent or spraying treatment of granules on the seedling bed. Application of the granules to the planting hole or mixing with the cultivation carrier near the transplanting site is also preferred. The agricultural and horticultural pest control agent of the present invention is generally formulated into a convenient form for use according to conventional methods for pesticide formulation. That is, the compound represented by the general formula (1) of the present invention or a salt thereof may be blended in an appropriate ratio with an appropriate inert carrier, or if necessary, an adjuvant, and then dissolved, separated, suspended, mixed, impregnated, adsorbed or attached to the carrier, and then formulated into an appropriate dosage form, such as a suspension, emulsion, solution, wettable powder, water dispersible granule, granule, dust, tablet, pack, etc., for use.

[0102] In addition to the active ingredient, the agricultural and horticultural pest control agent of the present invention can contain additives commonly used in pesticide formulations as needed. Examples of such additives include carriers such as solid carriers and liquid carriers, surfactants, dispersants, wetting agents, binders, tackifiers, thickeners, colorants, spreading agents, adhesives, antifreeze agents, anticaking agents, disintegrants, and antidecomposition agents. If necessary, preservatives, plant fragments, and the like may also be used as additives. These additives may be used alone or in combination of two or more.

[0103] Examples of solid carriers include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth, inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride, organic solid carriers such as synthetic silicic acid, synthetic silicates, starch, cellulose, and plant powders (e.g., sawdust, coconut shells, corn cobs, and tobacco stalks), plastic carriers such as polyethylene, polypropylene, and polyvinylidene chloride, urea, inorganic hollow bodies, plastic hollow bodies, and fumed silica (fumed silica, white carbon). These may be used alone or in combination of two or more.

[0104] Examples of liquid carriers include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol; polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin; polyhydric alcohol compounds such as propylene glycol ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, and cyclohexanone; ethers such as ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, and THF; normal paraffin; naphthene; Examples of suitable solvents include aliphatic hydrocarbons such as isoparaffin, kerosene, and mineral oil, aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, and alkylnaphthalene, halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, and dimethyl adipate, lactones such as γ-butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, and N-alkylpyrrolidinone, nitriles such as acetonitrile, sulfur compounds such as dimethyl sulfoxide, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, and castor oil, and water. These may be used alone or in combination of two or more.

[0105] Examples of surfactants used as dispersants or wetting agents include sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene dialkylphenyl ethers, polyoxyethylene alkylphenyl ether formalin condensates, polyoxyethylene polyoxypropylene block copolymers, polystyrene polyoxyethylene block polymers, alkyl polyoxyethylene polypropylene block copolymer ethers, polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, polyoxyethylene fatty acid bisphenyl ethers, polyalkylene benzyl phenyl ethers, polyoxyalkylene styryl phenyl ethers, acetylenic diols, polyoxyalkylene-added acetylenic diols, polyoxyethylene ether-type silicones, ester-type silicones, fluorine anionic surfactants such as alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl phenyl ether sulfates, polyoxyethylene styryl phenyl ether sulfates, alkylbenzenesulfonates, alkylarylsulfonates, ligninsulfonates, alkylsulfosuccinates, naphthalenesulfonates, alkylnaphthalenesulfonates, salts of formalin condensates of naphthalenesulfonic acid, salts of formalin condensates of alkylnaphthalenesulfonic acid, fatty acid salts, polycarboxylates, polyacrylates, N-methyl-fatty acid sarcosinates, resinates, polyoxyethylene alkyl ether phosphates, and polyoxyethylene alkylphenyl ether phosphates; cationic surfactants such as alkylamine salts such as laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride, and alkyldimethylbenzalkonium chloride;Amphoteric surfactants such as amino acid type or betaine type surfactants may be used alone or in combination of two or more types.

[0106] Examples of binders and tackifiers include carboxymethyl cellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol having an average molecular weight of 6,000 to 20,000, polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, phospholipids (e.g., cephalin, lecithin, etc.), cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compounds, crosslinked polyvinylpyrrolidone, copolymers of maleic acid and styrenes, (meth)acrylic acid copolymers, half esters of polymers composed of polyhydric alcohols and dicarboxylic acid anhydrides, water-soluble salts of polystyrene sulfonic acid, paraffin, terpene, polyamide resins, polyacrylates, polyoxyethylene, wax, polyvinyl alkyl ethers, alkylphenol-formalin condensates, and synthetic resin emulsions.

[0107] Examples of thickeners include water-soluble polymers such as xanthan gum, guar gum, diutan gum, carboxymethyl cellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch compounds, and polysaccharides, and inorganic fine powders such as high-purity bentonite and fumed silica (white carbon).

[0108] Examples of colorants include inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes.

[0109] Examples of antifreezing agents include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.

[0110] Examples of adjuvants for preventing caking or promoting disintegration include polysaccharides such as starch, alginic acid, mannose, and galactose, polyvinylpyrrolidone, fumed silica (white carbon), ester gum, petroleum resin, sodium tripolyphosphate, sodium hexametaphosphate, metal stearates, cellulose powder, dextrin, methacrylic acid ester copolymers, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compounds, sulfonated styrene-isobutylene-maleic anhydride copolymers, and starch-polyacrylonitrile graft copolymers.

[0111] Examples of anti-decomposition agents include desiccants such as zeolite, quicklime, and magnesium oxide; antioxidants such as phenol compounds, amine compounds, sulfur compounds, and phosphoric acid compounds; and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds.

[0112] Examples of preservatives include potassium sorbate, 1,2-benzothiazolin-3-one, etc. Furthermore, other adjuvants such as functional spreading agents, activity enhancers such as metabolic decomposition inhibitors such as piperonyl butoxide, antifreeze agents such as propylene glycol, antioxidants such as BHT, and ultraviolet absorbers can also be used as needed.

[0113] The blending ratio of the active ingredient compound can be adjusted as necessary, and may be appropriately selected from the range of 0.01 to 90 parts by weight per 100 parts by weight of the agricultural and horticultural pest control agent of the present invention. For example, when used as a dust, granule, emulsifiable concentrate or wettable powder, an amount of 0.01 to 50 parts by weight (0.01 to 50% by weight based on the total weight of the agricultural and horticultural pest control agent) is appropriate.

[0114] The amount of the agricultural and horticultural pest control agent of the present invention to be used will vary depending on various factors, such as the purpose, target pest, crop growth condition, pest occurrence tendency, weather, environmental conditions, formulation, application method, application location, application time, etc., but may be appropriately selected depending on the purpose from a range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg, of the active ingredient compound per 10 ares. The agricultural and horticultural pest control agent of the present invention can be used in combination with other agricultural and horticultural insecticides, miticides, nematicides, fungicides, biological pesticides, etc., in order to extend the target pests and diseases to be controlled, the optimal control period, or for the purpose of reducing the amount of application, and can also be used in combination with herbicides, plant growth regulators, fertilizers, etc., depending on the application scene.

[0115] Other agricultural and horticultural insecticides, acaricides, and nematicides used for such purposes include, for example, 3,5-xylyl methylcarbamate (XMC), fenobucarb (BPMC), Bt toxin-based insecticides, CPCBS (chlorfenson), DCIP (dichlorodiisopropyl ether), DD (1,3-dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O,O-diethyl phosphorothioate (DSP), O-ethyl O-4-nitrophenyl phenylphosphonothioate (EPN), tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, and acinonapyr. , azinphos-methyl, acequinocyl, acetamiprid, acetoprole, acephate, abamectin, afidopyropen, avermectin-B, amidoflumet, amitraz, alanycarb, aldicarb ), aldoxycarb, aldrin, alpha-endosulfan, alpha-cypermethrin, albendazole, allethrin, isazofos, isamidofos, isamidofos, isoxathion, isocycloseram, isofenphos, isoprocarb (MIPC), epsilon-metofluthrin,Epsilon-momfluorothrin, ivermectin, imicyafos, imidacloprid, imiprothrin, indazapyroxamet, indoxacarb, esfenvalerate, ethiofencarb ... Ethion, ethiprole, etoxazole, etofenprox, ethoprophos, etrimfos, emamectin, emamectin benzoate, endosulfan, empenthrin, oxazosulfyl, oxamyl, oxydemeton-methyl, oxydeprofos (ESP), oxibendazole, oxfendazole, potassium oleate, sodium oleate oleate, cadusafos, kappa-bifenthrin, cartap, carbaryl, carbosulfan, carbofuran, gamma-cyhalothrin, xylylcarb, quinalphos, kinoprene, chinomethionate, cloethocarb, clothianidin, clofentezine, chromafenozide, chlorantraniliprole, chlorethoxyfos,Chlordimeform, chlordane, chlorpyrifos, chlorpyrifos-methyl, chlorphenapyr, chlorfenson, chlorfenvinphos, chlorfluazuron, chlorobenzilate, chlorobenzoate, chloroprallethrin, kelthane (dicofol), salithion, cyhalodiamide, cyanophos CYAP), diafenthiuron, diamidaphos, cyantraniliprole, theta-cypermethrin, dienochlor, cyetpyrafen, cyenopyrafen, dioxabenzofos, diofenolan, sigma-cypermethrin, cyclaniliprole, diclofenthion (ECP), cycloprothrin, dichlorvos (dichlorvos: DDVP), dichloromezotiaz (dicloromezotiaz), disulfoton (disulfoton), dinotefuran (dinotefuran), cyhalodiamide (cyhalodiamide), cyhalothrin (cyhalothrin), cyphenothrin (cyphenothrin), cyfluthrin (cyfluthrin), diflubenzuron (diflubenzuron), cyflumetofen (cyflumetofen), diflovidadin (diflovidazin), cyproflanilide (cyproflanilide), cyhexatin (cyhexatin), cypermethrin (cypermethrin),Dimethylvinphos, dimethoate, dimpropyridaz, dimefluthrin, silafluofen, cyromazine, spidoxamat, spinetoram, spinosad, spirobudifen, spirodiclofen, spirotetramat, spiropidione, spiromesifen fen), sulfluramid, sulprofos, sulfoxaflor, zeta-cypermethrin, diazinon, tau-fluvalinate, dazomet, thiacloprid, thiamethoxam, tioxazafen, thiodicarb iodicarb), thiocyclam, thiosultap, thiosultap sodium, thionazin, thiometon, thiolanthraniliprole, DEET, dieldrin, tetrachlorantraniliprole, tyclopyrazoflor, tetrachlorvinphos, tetradifon, tetraniliprole, tetramethylfluthrin, tetramethrin, tebupirimfos, tebufenozide, tebufenpyrad, tefluthrin,Teflubenzuron, demeton-S-methyl, temephos, deltamethrin, terbufos, doramectin, tralopyril, tralomethrin, transfluthrin, triazamate, triazuron, trichlamide, trichlorphon (DEP), trifluenfuronate, triflumezopyrium, triflumuron, tolfenpyrad, naled BRP), nicofluprole, nithiazine, nitenpyram, novaluron, noviflumuron, hydroprene, vaniliprole, vamidothion, parathion, parathion-methyl, halfenprox, halofenozide, bistrifluron, bisultap, hydramethylnon, hydroxypropyl starch starch), binapacryl, piflubumide, bifenazate, bifenthrin, pymetrozine, pyraclofos, pyrafluprole, pyridaphenthion, pyridaben, pyridalyl, pyrifluquinazon, pyriprole,Pyriproxyfen, pirimicarb, pyrimidifen, pyriminostrobin, pirimiphos-methyl, pyrethrins, fipronil, fenazaquin, fenamiphos, phenisobromorate, fenitrothion (MEP), fenoxycarb, fenothiocarb, fenothrin, fenobucarb, fensulfothion, fenthion (MPP), phenthoate PAP), fenvalerate, fenpyroximate, fenpropathrin, fenbendazole, fenmezoditiaz, fosthiazate, formetanate, butathiofos , buprofezin (buprofezin), furathiocarb (furathiocarb), prallethrin (prallethrin), fluacrypyrim (fluacrypyrim), furazaindolizine (fluazaindolizine), fluazinam (fluazinam), fluazuron (fluazuron), fluensulfone (fluensulfone), fluxametamide (fluxametamide), fluchlordiniliprole (fluchlordiniliprole), flucycloxuron (flucycloxuron), flucythrinate (flucythrinate), fluvalinate (fluvalinate), flupyradifurone (flupyradifurone), flufiprole (flufiprole), flupyradifurone (flupyradifurone), flupyroxystrobin (flupyroxystrobin),Flupyrazofos, flupyrimin, flufenerim, flufenoxystrobin, flufenoxuron, flufenzine, flufenprox, fluproxyfen, flubrocythrinate, fluhexafon, flubendiamide, flupentiofenox, flumethrin, flurimfen, prothiofos, protrifenbute, flonicamid, propaphos, propargite BPPS), profenofos, broflanilide, profluthrin, propoxur (PHC), flometoquin, alpha-bromadiolone, bromopropylate, beta-cyfluthrin, hexaflumuron, hexythiazox, heptafluthrin, heptenophos, permethrin, benclothiazol az), bendiocarb, benzpyrimoxan, bensultap, benzoximate, benfuracarb, phoxim, phosalone, fosthiazate, fosthietan, phosphamidon, phosphocarb, phosmet (PMP),Polynactins, formetanate, formothion, phorate, machine oil, malathion, milbemycin, milbemycin A, milbemectin, mecarbam, mesulfenphos, methomyl, metaldehyde, metaflumizone, methamidophos, metam-ammonium, metam-sodium, methiocarb, methidathion: DMTP), methylisothiocyanate, methylneodecanamide, methylparathion, methoxamer Diazone (metoxadiazone), methoxychlor (methoxychlor), methoxyfenozide (methoxyfenozide), metofluthrin (metofluthrin), methoprene (methoprene), metolcarb (metolcarb), meperfluthrin (meperfluthrin), mevinphos (mevinphos), monocrotophos (monocrotophos), monosultap (monosultap), momfluorothrin (momfluorothrin), lambda-cyhalothrin (lambda-cyhalothrin), ryanodine (ryanodine), lufenuron (lufenuron), lescalure (rescalure), resmethrin (resmethrin), lepimectin (lepimectin), rotenone (rotenone), levamisol hydrochloride (levamisol hydrochloride), fenbutatin oxide (fenbutatin oxide), morantel tartrate (morantel tartarate), methyl bromide,Examples include tricyclohexyltin hydroxide (cyhexatin), calcium cyanamide, calcium polysulfide, sulfur, and nicotine sulfate.

[0116] Agricultural and horticultural fungicides used for similar purposes include, for example, aureofungin, azaconazole, azithiram, acipetax, acibenzolar, acibenzolar-S-methyl, azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, and allyl alcohol. alcohol), aldimorph (aldimorph), amobam (amobam), isotianil (isotianil), isovaledione (isovaledione), isopyrazam (isopyrazam), isofetamide (isofetamid), isoflucypram (isoflucypram), isoprothiolane (isoprothiolane), ipconazole (ipconazole), ipfentrifluconazole (ipfentrifluconazole), ipflufenoquin (ipflufenoquin), iprodione (iprodione), iprovalicarb (iprovalicarb), iprobenfos (iprobenfos), imazalil (imazalil), iminoctadine (iminoctadine), metam (metam), iminoctadine albesilate (iminoctadine-albesilate), iminoctadine acetate (iminoctadine-triacetate), imibenconazole (imibenconazole), inpyrfluxam (inpyrfluxam), uniconazole (uniconazole), uniconazole-P (uniconazole-P), echlomezole (echlomezole), edifenphos (edifenphos), etaconazole (etaconazole), ethaboxam (ethaboxam), ethirimol (ethirimol), etem (etem), ethoxyquin (ethoxyquin), etridiazole (etridiazole), enestroburin (enestroburin),Enoxastrobin, epoxiconazole, oxadixyl, oxathiapiprolin, oxycarboxin, copper-8-quinolinolate, oxytetracycline, copper-oxinate, oxpoconazole, oxpoconazole-fumarate, oxolinic acid acid), octhilinone, ofurace, orysastrobin, carbam (metam-sodium), kasugamycin, carbamorph, carpropamid, carbendazim, carboxin, carvone, quinazamid, quinacetol, quinoxyfen, quinofumelin, chinomethionate , quinomethionate), captafol (captafol), captan (captan), chiralaxyl (kiralaxyl), quinconazole (quinconazole), quintozene (quintozene), guazatine (guazatine), cufraneb (cufraneb), cuprobam (cuprobam), coumoxystrobin (coumoxystrobin), glyodin (glyodin), griseofulvin (griseofulvin), climbazole (climbazole), cresol (cresol), kresoxim-methyl (kresoxim-methyl), chlozolinate (chlozolinate), clotrimazole (clotrimazole), chlobenthiazone (chlobenthiazone), chloraniformethan (chloraniformethan), chloranil (chloranil),Chlorquinox, chloropicrin, chlorphenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, chloroneb, salicylanilide, zalilamid, cyazofamid, diethyl pyropacarbonate pyrocarbonate), diethofencarb, cyclafuramid, cyclocymet, dichlozoline, diclobutrazol, cyclobutrifluram, dichlofluanid, cycloheximide, dichlobentiazox, diclomezine, dicloran, dichlorophen, dichlorone, disulfiram, ditalimfos, dithianon, dithianon Niconazol (diniconazole), diniconazole-M (diniconazole-M), zineb (zineb), dinocap (dinocap), dinocton (dinocton), dinosulfon (dinosulfon), dinoterbone (dinoterbon), dinobuton (dinobuton), dinopenton (dinopenton), dipymetitrone (dipymetitrone), dipyrithione (dipyrithione), diphenylamine (diphenylamine), difenoconazole (difenoconazole), cyflufenamid (cyflufenamid), diflumetrim (diflumetorim), cyproconazole (cyproconazole), cyprodinil (cyprodinil), cyprofuram (cyprofuram),Cypendazole, simeconazole, dimethirimol, dimethomorph, cymoxanil, dimoxystrobin, ziram, silthiofam, streptomycin, spiroxamine, sultropen, sedaxane, zoxamide, dazomet, thiadiazin, tiadinil, thiadifluor, thiadifluor Avendazole, thioximid, thiochlorfenphim, thiophanate, thiophanate-methyl, thifluzamide, thicyofen, thioquinox, thiram, decafentin, tecnazene, tecloftalam, tecoram, tetraconazole, debacarb, dehydroacetic acid acid), tebuconazole (tebuconazole), tebufloquin (tebufloquin), dodicin (dodicin), dodine (dodine), dodecylbenzenesulfonic acid bisethylenediamine copper complex salt (II) (DBEDC), dodemorph (dodemorph), drazoxolon (drazoxolon), triadimenol (triadimenol), triadimefon (triadimefon), triazbutil (triazbutil), triazoxide (triazoxide), triamiphos (triamiphos), triarimol (triarimol), trichlamide (trichlamide), triclopyricarb (triclopyricarb), tricyclazole (tricyclazole),Triticonazole, tridemorph, tributyltin oxide, triflumizole, trifloxystrobin, triforine, tolylfluanid, tolclofos-methyl, tolprocarb, natamycin, nabam, nitrostyrene, nitrothal-isopropyl, nuarimol, copper nonylphenol sulfonate, halacrinate, validamycin, valifenalate, harpin protein protein), picarbutrazox, bixafen, picoxystrobin, picobenzamide, pydiflumetofen, bithionol, bitertanol, hydroxyisoxazole, hydroxyisoxazole-potassium, binapacryl, biphenyl , piperaline (piperalin), hymexazol (hymexazol), pyraoxystrobin (pyraoxystrobin), pyracarbolid (pyracarbolid), pyraclostrobin (pyraclostrobin), pyraziflumid (pyraziflumid), pyrazophos (pyrazophos), pyrapropoin (pyrapropoyne), pyrametostrobin (pyrametostrobin), pyriophenone (pyriofenone), pyridinitril (pyridinitril), pyridiflumetofen (pydiflumetofen),Pyrisoxazole, pyridaclomethyl, pyrifenox, pyribencarb, pyriminostrobin, pyrimethanil, pyroxychlor, pyroxyfur, pyroquilon, vinclozolin, ferbam, famoxadone ), fenapanil (fenapanil), fenamidone (fenamidone), fenaminosulf (fenaminosulf), phenaminestrobin (fenaminstrobin), fenarimol (fenarimol), fenitropan (fenitropan), fenoxanil (fenoxanil), ferimzone (ferimzone), ferbam (ferbam), fentin (fentin), fenpiclonil (fenpiclonil), fenpicoxamid (fenpicoxamid), fenpyrazamine ( fenpyrazamine, fenbuconazole, fenfuram, fenpropidin, fenpropimorph, fenhexamid, phthalide, buthiobate, butylamine, bupirimate, fuberidazole, blasticidin-S, furam Topil (furametpyr), furalaxyl (furalaxyl), fluacrypyrim (fluacrypyrim), fluazinam (fluazinam), fluindapyr (fluindapyr), fluoxastrobin (fluoxastrobin), fluoxapiprolin (fluoxapiprolin), fluoxytioconazole (fluoxytioconazole), fluotrimazole (fluotrimazole), fluopicolide (fluopicolide), fluopimomide (Fluopimomide),Fluopyram, fluoroimide, furcarbanil, fluxapyroxad, fluquinconazole, fluconazole, furconazole-cis, fludioxonil, flusilazole, flusulfamide, flutianil, fluthiazol-1, fluthiazol-2, fluthiazol-3, fluthiazol-4, fluthiazol-5, fluthiazol-6, fluthiazol-7, fluthiazol-8, fluthiazol-9, fluthiazol-10, fluthiazol-11, fluthiazol-12, fluthiazol-13, fluthiazol-14, fluthiazol-15, fluthiazol-16, fluthiazol-17, fluthiazol-18, fluthiazol-19, fluthiazol-20, fluthiazol-21, fluthiazol-22, fluthiazol-23, fluthiazol-24, fluthiazol-25, fluthiazol-26, fluthiazol-27, fluthiazol-28, fluthiazol-29 ... Tranil (flutolanil), flutriafol (flutriafol), flufenoxadiazam (flufenoxadiazam), flufenoxystrobin (flufenoxystrobin), furfural (furfural), flubeneteram (flubeneteram), flumecyclox (furmecyclox), flumethylsulfolim (flumetylsulforim), flumetbell (flumetover), flumorph (flumorph), proquinazid (proquinazid), prochloraz (prochloraz), procymidone (procymidone), prothiocarb (prothiocarb), prothioconazole (prothioconazole), pronitridine (pronitridine), propamocarb (propamocarb), propiconazole (propiconazole), propineb (propineb), furophanate (furophanate), probenazole (probenazole), bromuconazole (bromuconazole), florylpicoxamide ( florylpicoxamid), hexachlorobutadiene, hexaconazole, hexylthiofos, bethoxazin, benalaxyl, benalaxyl-M, benodanil, benomyl, pefurazoate, benquinox, penconazole,Benzamorph, pencycuron, benzohydroxamic acid, benzovindiflupyr, bentaluron, benthiazole, benthiavalicarb, benthiavalicarb-isopropyl, penthiopyrad, penflufen, boscalid, phosdiphen, fosetyl, fosetyl-aluminum, polyoxins, polyoxolin, polycarbamate, folpet, formaldehyde, machine oil oil), maneb, mancozeb, mandipropamid, mandestrobin, myclozolin, myclobutanil, mildiomycin, milneb, mecarbinzid, methasulfocarb, metazoxolone, metam, metam-sodium, metalaxyl, metalaxyl-M, metarylpicoxamid, metiram, methyl isothiocyanate isothiocyanate), methyldinocap (mepthyldinocap), methyltetraprole (Methyltetraprole), metconazole (metconazole), metsulfovax (metsulfovax), metofuroxam (methfuroxam), metominostrobin (metominostrobin), metrafenone (metrafenone), mepanipyrim (mepanipyrim),Inorganic disinfectants such as mefenoxam (mefenoxam), mefentrifluconazole (mefentrifluconazole), meptyldinocap (meptyldinocap), mepronil (mepronil), mebenil (mebenil), methyl iodide (iodomethane), rabenzazole (rabenzazole), methyl bromide (methyl bromide), benzalkonium chloride (benzalkonium chloride), basic copper chloride (basic copper chloride), basic copper sulfate (basic copper sulfate), metallic silver (silver), sodium hypochlorite (sodium hypochlorous acid), cupric hydroxide (cupric hydroxide), wettable sulfur (wettable sulfur), lime sulfur mixture (calcium polysulfide), potassium hydrogen carbonate (potassium hydrogen carbonate), sodium hydrogen carbonate (sodium hydrogen carbonate), inorganic sulfur (sulfur), anhydrous copper sulfate (copper sulfate anhydride), dimethyldithiocarbamate nickel (nickel dimethyldithiocarbamate), 8-hydroxyquinoline copper (oxine Examples include copper compounds such as zinc sulfate, copper sulfate pentahydrate, etc.

[0117] Similarly, herbicides such as 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, MCPA thioethyl, MCPB, ioxynil, aclonifen, azafenidin din), acifluorfen, aziprothrin, azimsulfuron, asulam, acetochlor, atrazine, atraton, anisuron, anilofos, aviglycine, abscisic acid acid), amicarbazone, amidosulfuron, amitrole, aminocyclopyrachlor, aminopyralid, amivudine, amiprophos-methyl, ametridione, ametryn, alachlor, allidochlor, alloxydim, arorac, iofensulfuron ensulfuron), isouron, isocarbamide, isoxachlortole, isoxapyrifop, isoxaflutole, isoxaben, isocil, isonoruron, isoproturon, isopropalin, isopolinate, isomethiozin, inabenfide, ipazine,Iptriazopyrid, ipfencarbazone, iprimidam, imazaquin, imazapic, imazapyr, imazamethapyr, imazamethabenz, imazamethabenz-methyl, imazamox, imazethapyr, imazosulfuron, indaziflam, indanofan, indolebutyric acid acid), uniconazole-P (uniconazole-P), eglinazine (eglinazine), esprocarb (esprocarb), ethametsulfuron (ethametsulfuron), ethametsulfuron-methyl (ethametsulfuron-methyl), ethalfluralin (ethalfluralin), ethiolate (ethiolate), ethychlozate-ethyl (ethychlozate-ethyl), ethidimuron (ethidimuron), ethinofen (etinofen), ethephon (ethephon), ethoxysulfuron (ethoxysulfuron), ethoxyfen (ethoxyfen), etnipromid (etnipromid), et Fumesate (ethofumesate), etobenzanid (etobenzanid), epirifenacil (epyrifenacil), epronaz (epronaz), erbon (erbon), endothal (endothal), oxadiazon (oxadiazon), oxadiargyl (oxadiargyl), oxaziclomefone (oxaziclomefone), oxasulfuron (oxasulfuron), oxapyrazon (oxapyrazon), oxyfluorfen (oxyfluorfen), oryzalin (oryzalin), orthosulfamuron (orthosulfamuron), orbencarb (orbencarb), cafenstrole (cafenstrole),Cambendichlor, carbasulam, carfentrazone, carfentrazone-ethyl, karbutilate, carbetamide, carboxazole, quizalofop, quizalofop-P, quizalofop-ethyl, xylaclor lachlor), quinoclamine, quinonamid, quinclorac, quinmerac, cumyluron, clacyfos, cliodinate, glyphosate, glufosinate, glufosinate-P, credazine, clethodim, cloxifonac oxyfonac), clodinafop (clodinafop), clodinafop-propargyl (clodinafop-propargyl), clotoluron (chlorotoluron), clopyralid (clopyralid), cloproxydim (cloproxydim), cloprop (cloprop), clobromuron (chlorbromuron), clofop (clofop), clomazone (clomazone), chlomethoxynil (chlomethoxyni1), chlomethoxyfen (chlomethoxyfen), clomeprop (clomeprop), chlorazifop (chlorazifop), chlorazine (chlorazine), chloranocryl (chloranocryl), chloramben (chloramben), cloransulam (cloransulam), chloransulam-methyl (cloransulam-methyl), chloridazon (chloridazon), chlorimuron (chlorimuron), chlorimuron-ethyl (chlorimuron-ethyl), chlorsulfuron (chlorsulfuron),Chlorthal, chlorthiamid, chlortoluron, chlornitrofen, chlorfenac, chlorfenprop, chlorbufam, chlorphthalim, chlorflurazole, chlorflurenol, chlorprocarb, chlorpropham, chlormequat, chloreturon, chloroxynil , chloroxuron, chlorotoluron, chloropon, saflufenacil, cyanazine, cyanatrin, di-allate, diuron, diethamquat, dioxopyritrione, dicamba, cycluron, cycloate, cycloxydim, diclosulam, cyclosulfamuron, cyclopyranil , cyclopyrimorate (cyclopyrimorate), dicloprop (dichlorprop), dicloprop-P (dichlorprop-P), dichlobenil (dichlobenil), diclofop (diclofop), diclofop-methyl (diclofop-methyl), dichromate (dichlormate), dichloralurea (dichloralurea), diquat (diquat), cisanilide (cisanilide), disul (disul), siduron (siduron), dithiopyr (dithiopyr), dinitramine (dinitramine), cinidon-ethyl (cinidon-ethyl), dinosam (dinosam),Cinosulfuron, dinoseb, dinoterb, dinofenate, dinoprop, cyhalofop-butyl, cypyrafluone, diphenamid, difenoxuron, difenopenten, difenzoquat, sibutryne, cipragil Cyprazine, cyprazole, diflufenican, diflufenzopyr, dipropetryn, cypromid, cyperquat, gibberellin, simazine, dimexano, dimesulfazet, dimethachlor, dimedazon , dimethametryn, dimethenamid, simetryn, simeton, dimepiperate, dimefuron, cinmethylin, swep, sulglycapin, sulcotrione, sulfalate, sulfentrazone, sulfosulfuron osulfuron), sulfometuron (sulfometuron), sulfometuron methyl (sulfometuron-methyl), secbumeton (secbumeton), sethoxydim (sethoxydim), sebuthylazine (sebuthylazine), terbacil (terbacil), daimuron (daimuron), dazomet (dazomet), dalapon (dalapon), thiazafluron (thiazafluron), thiazopyr (thiazopyr), thiafenacil (tiafenacil),Thiencarbazone, thiencarbazone-methyl, thiocarbazil, thioclorim, thiobencarb, thidiazimin, thidiazuron, thifensulfuron, thifensulfuron-methyl, desmedipham, desmedipham Desmetryn, tetflupyrolimet, tetrafluron, thenylchlor, tebutam, tebuthiuron, terbumeton, tepraloxydim, tefuryltrione, tembotrione, delachlor, terbacil, terbucarb terbucarb), terbuchlor (terbuchlor), terbuthylazine (terbuthylazine), terbutryn (terbutryn), topramezone (topramezone), tralkoxydim (tralkoxydim), triaziflam (triaziflam), triasulfuron (triasulfuron), triafamone (triafamone), triallate (tri-allate), trietazine (trietazine), tricamba (tricamba), triclopyr (triclopyr), tridiphane (tridiphane), tritac (tritac), tritosulfuron (tritosulfuron), tripyrasulfone (tripyrasulfone), trifludimoxazin (trifludimoxazin), triflusulfuron (triflusulfuron), triflusulfuron-methyl (triflusulfuron-methyl), trifluralin (trifluralin), trifloxysulfuron (trifloxysulfuron), tripropindan (tripropindan),Tribenuron, tribenuron-methyl, triphop, trifopsime, trimeturon, tolpyralate, naptalam, naproanilide, naproxen, nicosulfuron, nitralin, nitrofen, nitrofluorfen nitrofluorfen, nipyraclofen, neburon, norflurazon, noruron, barban, paclobutrazol, paraquat, parafluron, haloxydine, halauxifen, haloxyfop, haloxyfop-P, haloxyfop-P haloxyfop-methyl, halosafen, halosulfuron, halosulfuron-methyl, bialafos, bixlozone, picloram, picolinafen, bicyclopyrone, bispyribac, bispyribac-sodium, Danone (pydanon), pinoxaden (pinoxaden), bipyrazone (bipyrazone), bifenox (bifenox), piperophos (piperophos), hymexazol (hymexazol), pyraclonil (pyraclonil), pyrasulfotole (pyrasulfotole), pyrazoxyfen (pyrazoxyfen), pyrazosulfuron (pyrazosulfuron), pyrazosulfuron-ethyl (pyrazosulfuron-ethyl), pyrazolate (pyrazolate),Bilanafos, pyraflufen, pyraflufen-ethyl, pyriclor, pyridafol, pyrithioba c), pyrithiobac-sodium, pyridate, pyriftalid, pyributicarb, pyriflubenzoxim, pyribenzoxim, pyrimisulfan, pyrimisulfuron, pyriminobac-methyl, pyroxasulfone, pyroxsulam, fenasulam, fenisofam, fenuron, fenoxasulfone, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-ethyl, All (phenothio1), fenoprop (fenoprop), fenobenzuron (phenobenzuron), fenquinotrione (fenquinotrione), fentiaprop (fenthiaprop), fenteracol (fenteracol), fentrazamide (fentrazamide), fenpyrazone (fenpyrazone), phenmedipham (phenmedipham), phenmedipham-ethyl (phenmedipham-ethyl), butachlor (butachlor), butafenacil (butafenacil), butamifos (butamifos), buthiuron (buthiuron), buthidazole (buthidazole), butyrate (butylate), buturon (buturon), butenachlor (butenachlor), butoxydim (butroxydim), butralin (butralin), butroxydim (butroxydim),Flazasulfuron, flamprop, furyloxyfen, prynachlor, primisulfuron-methyl, fluazifop, fluazifop-P, fluazifop-butyl, fluazolate, fluroxypyr, fluothiuron, fluometuron, fluoroglycofen, flurochloridone, fluorodifen, fluoronitrofen, fluoromidine, flucarbazone, flucarbazone-sodium, fluchloraminopyr, fluchloraminopyr-tefuryl fluchloraminopyr-tefuryl), fluchloralin, flucetosulfuron, fluthiacet, fluthiacet-methyl, flusulfinam, flupyrsulfuron, flufenacet, flufenican, flufenoximacil, flufenpi Flufenpyr, flupropacil, flupropanate, flupoxam, flumioxazin, flumiclorac, flumiclorac-pentyl, flumipropyn, flumezin, fluometuron, flumetsulam, fluridone,Flurtamone, fluroxypyr, pretilachlor, proxan, proglinadin, procyazine, prodiamine, prosulfalin, prosulfuron, prosulfocarb, propaquizafop, propachlor, propazine, propanil, propyzamide, propisochlor, prohydrojasmon, propyrisulfuron, propham, profluazol, profluralin, prohexadione-calcium, propoxycarbazone ne), propoxycarbazone-sodium, profoxydim, bromacil, brompyrazone, prometryn, prometon, bromoxynil, bromofenoxim, bromobutide, bromobonil, florasulam, florpirauxifu florpyrauxifen, hexachloroacetone, hexazinone, petoxamid, benazolin, penoxsulam, pebulate, beflubutamid, beflubutamid-M, vernolate, perfluidone, bencarbazone,Benquitrione, benzadox, benzipram, benzylaminopurine, benzthiazuron, benzfendizone, bensulide, bensulfuron-methyl, benzoylprop, benzobicyclon, benzofenap, benzofluor (benzofluor), bentazone, pentanochlor, benthiocarb, pendimethalin, pentoxazone, benfluralin, benfuresate, fosamine, fomesafen, foramsulfuron, forchlorfenuron, maleic hydrazide hydrazide), mecoprop (mecoprop), mecoprop-P (mecoprop-P), medinoterb (medinoterb), mesosulfuron (mesosulfuron), mesosulfuron-methyl (mesosulfuron-methyl), mesotrione (mesotrione), mesoprazine (mesoprazine), mesoprothrin (methoprotryne), metazachlor (metazachlor), metazole (methazole), metazosulfuron (metazosulfuron), methabenzthiazuron (methabenzthiazuron), metamitron (metamitron), metamifop (metamifop), metam (metam), methalpropalin (methalpropalin), methiuron (methiuron), methiozolin (methiozolin), methiobencarb (methiobencarb), methyldymron (methyldymron), metoxuron (metoxuron), metosulam (metosulam),Metsulfuron, metsulfuron-methyl, metflurazon, metobromuron, metobenzuron, methometon, metolachlor, metribuzin, mepiquat chloride, mefenacet, mefluidide, monalide, monisouron, monunuron, monochloroacetic acid Examples of such antibacterial agents include iodosulfuron, iodosulfuron-methyl-sodium, iodobonil, iodomethane, lactofen, lancotrione, linuron, rimisoxafen, rimsulfuron, lenacil, rhodetanil, calcium peroxide, and methyl bromide.

[0118] In addition, examples of biological pesticides include virus preparations such as nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), and entomopoxi virus (EPV); microbial pesticides used as insecticides or nematicides such as Monacrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, and Pasteuria penetrans; and pesticides such as Trichoderma lignorum, Agrobacterium radiobactor, and non-pathogenic Erwinia carotovora. Similar effects can be expected by mixing it with microbial pesticides used as fungicides, such as Bacillus carotovora and Bacillus subtilis, or biological pesticides used as herbicides, such as Xanthomonas campestris.

[0119] Furthermore, as biological pesticides, for example, natural enemies of Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusa sibirica, Phytoseiulus persimilis, Amblyseius cucumeris, Orius sauteri, and the like, and Beauveria brongniartii, It is also possible to use the compound in combination with a microbial pesticide such as Erythritol brongniartii, or a pheromone agent such as (Z)-10-tetradecenyl acetate, (E,Z)-4,10-tetradecadinyl acetate, (Z)-8-dodecenyl acetate, (Z)-11-tetradecenyl acetate, (Z)-13-icosen-10-one, or 14-methyl-1-octadecene.

[0120] The compound represented by general formula (1) of the present invention or a salt thereof is also suitable for controlling animal parasites. Animal parasites live inside or on the body surface of a host animal and cause disadvantages to the host animal. They are roughly divided into ectoparasites that live on the body surface of a host animal and endoparasites that live inside the body. The compound represented by general formula (1) of the present invention or a salt thereof can also be used as an animal ectoparasite control agent or an animal endoparasite control agent.

[0121] When the compound represented by the general formula (1) or a salt thereof of the present invention is used as an animal ectoparasite control agent or an animal endoparasite control agent, examples of animals to which it can be applied include, but are not limited to, livestock such as pigs, horses, cattle, sheep, goats, rabbits, camels, buffalo, deer, mink, and chinchillas, pets such as dogs, cats, small birds, and monkeys, laboratory animals such as rats, mice, golden hamsters, and guinea pigs, poultry such as chickens, ducks, Aigamo ducks, quails, ducks, geese, and turkeys, and humans. It can also be applied to farmed fish such as sea bream, flounder, tuna, yellowtail, and eel, and crustaceans and shellfish such as shrimp, crabs, scallops, oysters, clams, and clams.

[0122] Examples of ectoparasites that can be controlled by the animal ectoparasite control agent of the present invention include species of the genus Rhipicephalus (e.g., Rhipicephalus (Boophilus) microplus, Rhipicephalus sanguineus), the genus Amblyomma, the genus Dermacentor, the genus Haemaphysalis, the genus Hyalomma, the genus Ixodes, the genus Rhipicentor, the genus Margaropus, the genus Argas, the genus Otobius, the genus Ornithodoros, the genus Chorioptes (e.g., Chorioptes bovis), the genus Psoroptes (e.g., Psoroptes ovis), the genus Cheyletiella, the genus Dermanyssus (e.g., Dermanyssus gallinae), the genus Ortnithonyssus, the genus Demodex (e.g., Demodex canis), the genus Sarcoptes (e.g., Sarcoptes scabiei), the genus Psorergates, the order Siphonaptera (e.g., Ctenocephalides felis, Ctenocephalides canis, etc.), Diptera (Musca spp, Gasterophilus intestinalis, Oestrus ovis, etc.), Phthiraptera (Bovicola Ovis, Bovicola Bovis, etc.), Lepidoptera, Coleoptera, Homoptera, genera Haematopota, Tabunus, Haematobia (Haematobia irritans, etc.), Stomoxys, Lucilia, Lepeophtheirus, etc.

[0123] More specifically, examples of mites include Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis campanulata, Haemaphysalis concinna, Haemaphysalis japonica, Haemaphysalis kitaokai, Haemaphysalis ias, Ixodes ovatus, Ixodes nipponensis, Ixodes persulcatus, Amblyommatestudinarium, Haemaphysalis ticks such as Dermacentor megaspinosa, Dermacentor reticulatus, and Dermacentor taiwanesis; fowl mites such as Dermacentor gallinae, Ornithonyssus sylviarum, and Ornithonyssus bursa; Asian chiggers (Eutrombicula wichmanni), red lobules (Leptotrombidium akamushi), Leptotrombidium pallidum, Leptotrombidium fuji, Leptotrombidium tosa, European leaf mites (Neotrombicula autumnalis), American chiggers (Eutrombicula alfreddugesi), and Miyagawatamamatsumushi (Helenicula chiggers such as the dog tick (Cheyletiella yasguri) and the rabbit tick (Cheyletiellaparasitivorax) and Cheyletiella blakei; Scabies mites such as Psoroptes cuniculi, Chorioptes bovis, Otodectes cynotis, Sarcoptes scabiei, and Notoedres cati; and Demodex mites such as Demodex canis.

[0124] Examples of fleas include the Pulicidae family and the Ceratephyllus family. Examples of fleas belonging to the Pulicidae family include the dog flea (Ctenocephalides canis), cat flea (Ctenocephalides felis), human flea (Pulex irritans), chicken flea (Echidnophaga gallinacea), Cheops flea (Xenopsylla cheopis), mole rat flea (Leptopsylla segnis), European mouse flea (Nosopsyllus fasciatus), and Japanese mouse flea (Monopsyllus anisus).

[0125] Other examples of ectoparasites that can be controlled by the animal ectoparasite control agent of the present invention include lice such as cattle lice (Haematopinus eurysternus), horse lice (Haematopinus asini), sheep lice (Dalmalinia ovis), cattle lice (Linognathus vituli), pig lice (Haematopinus suis), pubic lice (Phthirus pubis), and head lice (Pediculus capitis), as well as biting lice such as dog biting lice (Trichodectes canis), and blood-sucking Diptera pests such as horse flies (Tabanus trigonus), horse midges (Culicoides schultzei), and black gnats (Simulium ornatum).

[0126] The animal ectoparasite-controlling agent of the present invention may be prepared by using a suitable solid or liquid carrier according to a commonly used formulation, blending the agent in an appropriate ratio with, if necessary, adjuvants, etc., followed by dissolving, suspending, mixing, impregnating, adsorbing, or adhering the agent to an appropriate dosage form depending on the intended use, such as a liquid, emulsion, cream, ointment, suspension, or aerosol. The active ingredient in these formulations may be blended in an amount of 0.01 to 80.0 parts by mass of the active ingredient per 100 parts by mass of the formulation. The solid or liquid carrier used may be a carrier typically used in veterinary drugs, with the use of a liquid carrier being preferred due to ease of application to the target animal. Examples of liquid carriers include alcohols such as methyl alcohol, ethyl alcohol, isopropyl alcohol, tertiary butyl alcohol, and benzyl alcohol, propylene carbonate, N-methyl-2-pyrrolidone, and water. An adjuvant can be used as needed, and examples of adjuvants that can be used include surfactants, antioxidants, emulsifiers, and the like. Examples include surfactants such as polyoxyethylene alkylaryl ether, polyoxyethylene sorbitan monolaurate, alkylarylsorbitan monolaurate, alkylbenzenesulfonates, alkylnaphthalenesulfonic acids, ligninsulfonate higher alcohol sulfates, glycol monoalkyl ethers, and glycols; emulsifiers such as sorbitan monooleate, sorbitan monolaurate, caprylic acid monoglyceride, capric acid monoglyceride, isostearic acid monoglyceride, and propylene glycol monocaprylate; and antioxidants such as BHA and BHT.

[0127] The veterinary ectoparasite control agent of the present invention may be administered to animals by any route that produces the desired effect, such as topical, oral, parenteral, or subcutaneous, and is not particularly limited, although topical administration is preferred. Local administration can be achieved by spot-on treatment, in which a liquid agent is dripped onto the skin of the dorsal scapular region of the target animal, pour-on treatment, in which a liquid agent is applied along the back line of the target animal, spray-on or spray-race treatment, in which a liquid aerosol agent is applied by spraying, or by dipping, or by treatment using ear tags or collars carrying the agent. The application amount is typically selected from the range of about 0.1 to 500 mg of the active ingredient compound and typically about 0.01 to 20 ml of the control agent of the present invention per kg of body weight of the target animal.

[0128] If necessary, other active ingredients may be used in combination, for example, afoxolaner, fluralaner, lotilaner, surolaner, mivoraner, modoflaner, tigolaner, umifoxolaner, albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxyfendazole, parabendazole, thiabendazole, triclabendazole, amitraz, demiditraz, clorsulon, closantel, oxyclonazide, lafoxanide, cyphenothrin (cyp henothrin), flumethrin, permethrin, cyromazine, derquantel, diamphenetide, dicyclanil, dinotefuran, imidacloprid, nitenpyram, thiamethoxam, abamectin, doramectin, emamectin, eprinomectin, ivermectin, moxidectin, selamectin, milbemycin oxime oxime), emodepside, epsiprantel, fipronil, fluazuron, fluhexafon, indoxacarb, levamisole, lufenuron, metaflumizone, methoprene, monepantel, morantel, niclosamide, nitroscanate, nitroxynil, novaluron, oxantel, praziquantel, pyrantel, pyriprole, pyriproxyfen, cisapronil, spinosad, spinetoram, triflumezopyrim, etc. When used in combination, two or more active ingredients may be mixed before administration, or two or more different preparations may be administered separately.

[0129] The endoparasites that can be controlled by the animal endoparasite-controlling agent of the present invention are broadly classified into protozoa and helminths. Examples of protozoa that parasitize humans include amoebas (Rhizopoda) such as Entamoeba histolytica, flagellates (Mastigophora) such as Leishmania, Trypanosoma, and Trichomonas, sporozoa (Sporozoa) such as Plasmodium and Toxoplasma, and ciliates (Ciliophora) such as Balantidium coli. Examples of helminths that parasitize humans include roundworms, Anisakis, dog roundworms, Trichostrongylus worms, pinworms, hookworms (Ancylostoma dubnii, Ancylostoma americanum, Ancylostoma brasiliensis, etc.), Angiostrongylus nematode, Gnathostoma nigroma, heartworms (filariasis, Wuchereria bancrofti, Brugia malayi, etc.), Onchocerca, Dracaena worms, and Trichostoma trichiata. Examples of such tapeworms include, but are not limited to, nematodes (Nematoda) such as Strongyloides stercoralis, Acanthocephala such as Acanthocephala giant, iron nematodes (Gordiacea) such as wireworms, leeches (Hirudinea) such as Japanese leeches, Schistosoma mansoni, Schistosoma haematobium, liver fluke, heterophyon fluke, fluke, and lung fluke (Trematoda), tapeworms (Taenia spp., Fox Worm, Fox Worm, Diplogonum major, Taenia tapeworms, (Taenia saginata, Taenia solium, Echinococcus hydatid, etc.), pattern tapeworms, Tapeworms gourd, Tapeworms scleractinianus, Tapeworms scleractinianus, monkey tapeworms, and tapeworms (Taenia nivelinus).

[0130] As protozoa that parasitize mammals or birds other than humans, the Apicomplexa includes coccidia such as Eimeria, Isospora, Toxoplasma, Neospora, Sarcocystis, Besnoitia, Hammondia, Cryptosporidium, and Caryospora. Other apicomplexan species include Hepatozoon, Haemosporina, such as Cocidia, Leucocytozoon, and Plasmodium, and Piroplasma, such as Theileria, Anaplasma, Eperythrozoon, Haemobartonella, and Rhrlichia. Microspora, such as Haemogregarina; Mastigophora, such as Encephalitozoon and Nosema; Trypanosomatids, such as Trypanosoma and Leishmania; Chilomastix, Trichomonas, Monocercomonas Onas, Histomonas, and other Trichomonadida, Hexamita, Giardia, and other Diplomonadida, Sarcodina, and other Amoeba, such as Entamoeba, and Ciliates, such as Balantidium, Buxtonella, and Entodinium, and other ruminal ciliates.

[0131] Examples of helminths that parasitize animals belonging to mammals or birds other than humans include nematodes such as pig roundworms (Ascaris), dog roundworms and cat roundworms (Toxocara), dog small roundworms (Toxascaris), horse roundworms (Parascaris), chicken roundworms (Ascaridia), chicken appendicitis worms (Heterakis), and roundworms (Ascarida) such as anisakis, pinworms (Oxyurida) such as horse pinworms (Oxyuris) and rabbit pinworms (Passalurus), horse strongyles (Strongylus), and haemonchus contortus. chus), Ostertagia, Trichostrongylus, Cooperia, Nematodirus, Hystrongylus, Oesophagostomum, Chabertia, Ancylostoma, Uncinaria, Necator, Bunostomum, Dictyocaulus, Metas Strongylida such as Filaroides, Aelurostrongulus, Angiostrongylus, Syngamus, Stephanurus, Strongyloides, Micronema, Thelazia, Oxyspirura, Spirocerca, Gong Spirurida nematodes such as Dirofilaria, Setaria, Dipetalonema, Parafilaria, Onchocerca, and other filarial worms, Parafilaria,Enoplida species such as Okinawa heartworm (Stephanofilaria), dog whipworm (Trichuris), cattle hair worm (Capillaria), rat bladder hair worm (Trichosomoides), Trichinella, and kidney worm (Dioctophyma)

[0132] Trematodes include the Fasciolata, such as the liver fluke (Fasciola) and the Fasciolopsis; the Paramphistomatidae, such as the Homalogaster; the Dicrocoelata, such as the Eurytrema and the Dicrocoelium; the Diplostomata, such as the Pharyngostomum and the Alaria; the Echinostoma, Echinochloa, and the Echinochloa. chinochasmus), Echinostomata, Paragonimus, Nanophyetus, and other Troglotrematoidea, Clonorchis, Heterophyida, Prosthogonimus, and other Plagiorchiida, and other Japanese flukes. Schistosoma and other blood flukes, tapeworms such as Diphyllobothrium and Spirometra, Pseudophylidea, Anoplocephara, Paranoplocephala, Moniezia, Dipylidium, Mesocestoides, bean tapeworms, Tenia, Hydatigera, and multi-headed tapeworms. Tapeworms include Multiceps, Echinococcus, Taenia, Taeniarhynchus, Hymenolepis, Vampirolepis, Raillietina, and Amoebotaenia, which are members of the Cyclophyllidea family; hookworms include Macracanthorhynchus and Moniliformis, which are members of the tongue worm family;Other parasitic worms include, but are not limited to, Linguatula, and various other parasites.

[0133] Furthermore, as for helminths, for example, the nematodes of the genus Enoplida include Trichuris spp., Capillaria spp., Trichomosoides spp., Trichinella spp., etc.; the genus Rhabditia include Micronema spp. and Strongyloides spp.; and the genus Strongylida include Stronylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp. spp.), Cylindropharynx spp., Poteriostomum spp., Cyclococcercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp., Stephanurus spp., Ancylostoma spp., Uncinaria spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp. spp.), Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp.), Spicocaulus spp., Elaphostrongylus spp., Parelaphostrongylus spp., Crenosoma spp., Paraclenosoma spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Marshallagia spp., Cooperia spp. spp.), Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., and Ollulanus spp.

[0134] Examples of the genus Oxyurida include Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp., and Heterakis spp.; examples of the family Ascaridia include Ascaris spp., Toxascaris spp., Toxocara spp., Parascaris spp., Anisakis spp., and Ascaridia spp.; examples of the genus Spiruride include Gnathosma spp. Examples of the genus Filariida include, for example, Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoides spp., Brugia spp., and the like. Examples of the genus Filariida include, for example, Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoides spp., Brugia spp., and the like. spp.), Wuchereria spp., Onchocerca spp., etc.

[0135] Examples of Acanthocephala include Filicollis spp., Moniliformis spp., Macracanthorhynchus spp., and Prosthenorchis spp.; examples of the Monogenea subclass of Trematoda include Gyrodactylus spp., Dactylogyrus spp., and Polystoma spp.; examples of the Digenea subclass include Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., and Trichobilharzia spp. spp.), Ornithbilharzia spp., Austrobilharzia spp., Gigantobilharzias spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp. spp.), Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantcotyle spp., Fischoederius spp., Gastrothylacus spp.), Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp., Metorchis spp., Heterophyes spp. and Metagonimus spp. spp.) etc.

[0136] Examples of the Pseudophyllidea tapeworms include Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., and Diplogonoporus spp.; examples of the Cyclophyllidea tapeworms include Mesocestoides spp., Anoplocephala spp., Paranoplocehala spp., Moniezia spp., Thysanosomsa spp., Thysaniezia spp., and spp.), Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp., Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp. Examples of parasites include, but are not limited to, parasites belonging to species such as Diplopylidium spp. and Diplopylidium spp., as well as various other parasites belonging to the classes Acanthopanax and Glossophora.

[0137] The animal endoparasite control agent of the present invention is effective not only against parasites living in the bodies of intermediate and definitive hosts, but also against parasites in the living body of a reservoir host. Furthermore, the compound represented by general formula (1) of the present invention exerts a control effect on all developmental stages of parasites. For example, in protozoa, this includes cysts, pre-encysted forms, trophozoites, or schizonts in the asexual reproductive stage, amoeboids, gametocytes, gametes, fusion bodies, and sporophytes in the sexual reproductive stage. In nematodes, this includes eggs, larvae, and adults. Furthermore, the compound of the present invention not only exterminates parasites in the living body, but can also prevent parasitic infection by applying it to the environment, which is a route of infection. For example, it is possible to prevent infections transmitted through soil from the soil in fields and parks, percutaneous infection from water systems such as rivers, lakes, marshes, and rice paddies, oral infection from the feces of animals such as dogs and cats, oral infection from saltwater fish, freshwater fish, crustaceans, shellfish, and raw livestock meat, and infections from mosquitoes, horseflies, flies, cockroaches, mites, fleas, lice, assassin bugs, and chiggers.

[0138] The animal endoparasite control agent of the present invention can be administered as a pharmaceutical to humans, non-human mammals, or birds for the purpose of treating or preventing parasitic diseases. It can be administered either orally or parenterally. For oral administration, it can be administered in the form of capsules, tablets, pills, powders, granules, fine granules, powders, syrups, enteric-coated formulations, suspensions, pastes, or by incorporating it into liquid drinks or animal feed. For parenteral administration, it can be administered in a dosage form that maintains mucosal or transdermal absorption, such as injections, drips, suppositories, emulsions, suspensions, drops, ointments, creams, solutions, lotions, sprays, aerosols, patches, or tapes.

[0139] When the animal endoparasite control agent of the present invention is used as a pharmaceutical for humans, non-human mammals, or birds, the optimal amount (effective amount) of the active ingredient varies depending on whether it is for treatment or prevention, the type of infecting parasite, the type and degree of infection, the dosage form, etc., but generally, in the case of oral administration, it is in the range of about 0.0001 to 10,000 mg / kg body weight per day. In the case of parenteral administration, it is in the range of about 0.0001 to 10,000 mg / kg body weight per day, and is administered in a single dose or in divided doses.

[0140] The concentration of the active ingredient in the animal endoparasite-controlling agent of the present invention is generally about 0.001 to 100% by mass, preferably about 0.001 to 99%, and more preferably about 0.005 to 20% by mass. The animal endoparasite-controlling agent of the present invention may be a composition to be administered as is, or may be a high-concentration composition to be diluted to an appropriate concentration before use.

[0141] In addition, for the purpose of reinforcing or complementing the effect of the animal endoparasite control agent of the present invention, the above-mentioned other active ingredients can be used in combination as needed. When using them in combination, two or more active ingredients may be mixed before administration, or two or more different formulations may be administered separately.

[0142] Representative examples of the present invention will be given below, but the present invention is not limited to these.

[0143] Production Example 1 Production of 6-(3-chloro-4-(trifluoromethyl)phenyl)-N-(4-fluorophenyl)-4-hydroxy-2-oxo-5,6-dihydro-2H-pyran-3-carboxamide (Compound No. 1-1)

[0144] 6-(3-chloro-4-(trifluoromethyl)phenyl)dihydro-2H-pyran-2,4(3H)-dione (220 mg, 0.752 mmol) was dissolved in tetrahydrofuran (2.00 mL), and 4-fluorophenyl isocyanate (128 μL, 1.13 mmol) and 60 wt% sodium hydride (45.1 mg, 1.13 mmol) were added at room temperature. The reaction solution was then stirred at room temperature for 6 hours, 1N hydrochloric acid was added, and the mixture was extracted three times with ethyl acetate. The obtained crude product was purified by column chromatography to give 6-(3-chloro-4-(trifluoromethyl)phenyl)-N-(4-fluorophenyl)-4-hydroxy-2-oxo-5,6-dihydro-2H-pyran-3-carboxamide (166 mg, 0.386 mmol). Yield: 51%. Physical properties: melting point 205°C.

[0145] Preparation Example 2 Preparation of N-(4-fluorophenyl)-5-hydroxy-3-oxo-1-(4-(trifluoromethyl)phenyl)-2-oxaspiro[5.5]undec-4-ene-4-carbothioamide (Compound No. 1-68)

[0146] 1-(4-(trifluoromethyl)phenyl)-2-oxaspiro[5.5]undecane-3,5-dione (70.0 mg, 0.210 mmol), N,N-dimethylacetamide (1 mL), 4-fluorophenyl isothiocyanate (40.0 mg, 0.257 mmol), and DBU (40.0 mg, 0.257 mmol) were added sequentially at room temperature, and the mixture was stirred at that temperature for 1 hour. After the reaction was completed, tert-butyl methyl ether and saturated aqueous ammonium chloride were added, and the mixture was separated. The organic layer was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give N-(4-fluorophenyl)-5-hydroxy-3-oxo-1-(4-(trifluoromethyl)phenyl)-2-oxaspiro[5.5]undec-4-ene-4-carbothioamide (60.0 mg, 0.126 mmol). Yield: 60% Physical properties: Melting point 74-76°C

[0147] Reference Example 1: Preparation of 1-(4-(trifluoromethyl)phenyl)-2-oxaspiro[5.5]undecane-3,5-dione Reference Example 1-1: Preparation of ethyl 3-(1-(hydroxy(4-(trifluoromethyl)phenyl)methyl)cyclohexyl)-3-oxopropanoate

[0148] Tetrahydrofuran (5 mL) and 60 wt% sodium hydride (330 mg, 8.31 mmol) were sequentially added to a 50 mL three-necked round-bottom flask under ice cooling. A tetrahydrofuran solution (3 mL) of ethyl 3-cyclohexyl-3-oxopropanoate (1.00 g, 6.93 mmol) was slowly added at that temperature. The mixture was then warmed to room temperature and stirred under an argon atmosphere for 20 minutes. Lithium diisopropylamide (4.0 mL, 8.31 mmol, 2.0 M tetrahydrofuran / heptane solution) was slowly added in an ice bath, the mixture was warmed to room temperature, and the mixture was stirred under an argon atmosphere for 20 minutes. The bath was replaced with an acetone / dry ice bath, and the mixture was cooled to -70°C. A tetrahydrofuran solution (3 mL) of 4-(trifluoromethyl)benzaldehyde (1.40 g, 8.31 mmol) was then added under an argon atmosphere. The mixture was then warmed to room temperature and stirred for 2 hours. After the reaction was completed, tertiary butyl methyl ether and 1N hydrochloric acid were added, and the mixture was separated. The organic layer was washed with saturated saline. The organic layer was dried over anhydrous sodium sulfate and filtered, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain ethyl 3-(1-(hydroxy(4-(trifluoromethyl)phenyl)methyl)cyclohexyl)-3-oxopropanoate (1.00 g, 3.67 mmol). Yield: 53%. Physical properties: 1 H-NMR (CDCl3): 7.59 (2H, d), 7.39 (2H, d), 4.73 (1H, d,), 4.22 (2H, m), 3.84 (1H, d), 3 .59 (1H, d), 2.61 (1H, d,), 2.27 (1H, m), 2.05 (2H, m), 1.72-1.02 (7H, m), 0.88 (3H, m)

[0149] Reference Example 1-2 Preparation of 1-(4-(trifluoromethyl)phenyl)-2-oxaspiro[5.5]undecane-3,5-dione

[0150] Ethyl 3-(1-(hydroxy(4-(trifluoromethyl)phenyl)methyl)cyclohexyl)-3-oxopropanoate (1.00 g, 2.50 mmol), ethanol (10 mL), and potassium carbonate (1.00 g, 7.50 mmol) were added sequentially, and the mixture was heated to reflux for 1 hour. After completion of the reaction, the solvent was evaporated under reduced pressure, and 1N hydrochloric acid and ethyl acetate were added to separate the layers, and the organic layer was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1-(4-(trifluoromethyl)phenyl)-2-oxaspiro[5.5]undecane-3,5-dione (364 mg, 1.1 mmol). Yield: 44%. Properties: 1 H-NMR (CDCl3): 7.69-7.65 (2H, m), 7.41-7.37 (2H, m), 5.36 (1H, s), 3.60 (2H, m), 1.92-1.73 (2H, m), 1.33-1.18 (6H, m), 1.09-1.00 (1H, m), 0.88 (2H, m) Formulation examples are shown below, but the present invention is not limited to these. In the formulation examples, parts indicate parts by weight.

[0151] Formulation Example 1 Compound of the present invention 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts The above ingredients are mixed and dissolved uniformly to prepare an emulsifiable concentrate.

[0152] Formulation Example 2: Compound of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above ingredients are uniformly mixed and pulverized to give a dust.

[0153] Formulation Example 3 Compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts Calcium lignosulfonate 5 parts The above ingredients are uniformly mixed, and an appropriate amount of water is added, followed by kneading, granulation and drying to give granules.

[0154] Formulation Example 4: Compound of the present invention 20 parts Kaolin and synthetic highly dispersed silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts The above ingredients are uniformly mixed and pulverized to give a wettable powder.

[0155] Examples of biological tests are shown below, but the present invention is not limited to these.

[0156] Test Example 1. Insecticidal test against diamondback moth (Plutella xylostella) Adult diamondback moths were released onto Chinese cabbage seedlings to allow them to lay eggs. Two days after release, the Chinese cabbage seedlings with the eggs were immersed for approximately 30 seconds in a chemical solution prepared by diluting a chemical containing the compound represented by general formula (1) of the present invention as an active ingredient to 500 ppm, and after air drying, the seedlings were left to stand in a thermostatic chamber at 25°C. Six days after immersion in the chemical solution, the number of surviving insects was counted, and the corrected insect mortality rate was calculated using the following formula, and the results were evaluated according to the following evaluation criteria. 10 insects per plot, 3 replicates.

[0157]

[0158] Judgment criteria. A... Mortality rate 100% B... Mortality rate 99% to 90% C... Mortality rate 89% to 80% D... Mortality rate 79% to 50% E... Mortality rate 49% to 0%

[0159] As a result, the compounds represented by general formula (1) of the present invention showed significant insecticidal activity, and in particular, compounds Nos. 1-1, 1-2, 1-5, 1-6, 1-7, 1-14, 1-15, 1-21, 1-22, 1-31, 1-67, 1-73, 1-74, 1-75, 1-76, 1-77, 1-78, 1-83, 1-84, 1-85, 1-86, 1-97, 1-103, 1-107, 1-131, 1-132 and 1-135 showed excellent activity against diamondback moth, with a rating of D or higher.

[0160] Test Example 2. Insecticidal test against small brown planthopper (Laodelphax striatellus) The compound represented by the general formula (1) of the present invention or a salt thereof was dispersed in water and diluted to a 500 ppm drug solution. Rice seedlings (variety: Nipponbare) were immersed in the drug solution for 30 seconds, air-dried, and then placed in glass test tubes. Ten third-instar Laodelphax striatellus insects were inoculated into each tube, and the tubes were then plugged with cotton. Eight days after inoculation, the number of live and dead insects was counted, and the corrected insect mortality rate was calculated using the following formula and evaluated according to the evaluation criteria of Test Example 1.

[0161]

[0162] As a result, among the compounds represented by general formula (1) of the present invention, compounds Nos. 1-21, 1-71, 1-75 and 1-76 showed excellent activity against the small brown planthopper, rated D or better.

[0163] Test Example 3. Insecticidal test against Frankliniella occidentalis: Female adult Frankliniella occidentalis were inoculated onto kidney bean leaf pieces, and after one day of egg laying, the female adult was removed. After a further three days, the number of hatched larvae on the leaf pieces was counted, and then a solution of a pesticide containing the compounds listed in Tables 1 to 3 as active ingredients, diluted to 500 ppm, was sprayed onto the leaves. Four days after treatment, the number of surviving larvae of this species was counted, and the corrected insect mortality rate was calculated using the following formula and evaluated according to the evaluation criteria of Test Example 1. 2 replicates were performed.

[0164]

[0165] As a result, the compounds of the present invention represented by general formula (1) showed significant insecticidal activity, and in particular, compounds Nos. 1-2, 1-21, 1-75 and 1-77 showed excellent activity against western flower thrips, with a rating of D or higher.

[0166] Test Example 4. Test to evaluate the effect on the growth of dog heartworms (Dirofilaria immitis) A predetermined preparation solution, 8-20 L-3 stage larvae of dog heartworms, and a DMSO diluted solution of the compound of the present invention were added to each well of a 24-well plate to make the final concentration 10 μM. Seven days later, the number of larvae that had developed to the L-4 stage was counted, and the growth inhibition rate from the L3 stage larvae to the L4 stage larvae was calculated.

[0167] As a result, among the compounds represented by general formula (1) of the present invention, compounds Nos. 1-1, 1-2, 1-8, 1-14, 1-15, 1-22, 1-23, 1-24, 1-27, 1-28, 1-29, 1-67, 1-68, 1-69, 1-70, 1-72, 1-73, 1-74, 1-75, 1-76, 1-77 and 1-78 showed a growth inhibition rate of 50% or more.

[0168] The compounds of the present invention and salts thereof have excellent effects as pest control agents.

Claims

1. General formula (1) 【Chemical 1】 {During the ceremony, R 1 teeth, (a1) Hydrogen atom; (a2) (C 1 -C 6 ) an alkyl group; or (a3) ​​a phenyl group. R 2 and R 3 teeth, (b1) a hydrogen atom; (b2) (C 1 -C 6 ) alkyl group; (b3) (C 1 -C 6 ) alkoxy(C 1 -C 6 ) alkyl group; (b4) N-(C 1 -C 6 ) alkylamino (C 1 -C 6 ) alkyl group; (b5) (C 1 -C 6 ) alkoxycarbonylamino (C 1 -C 6 ) an alkyl group; or (b6) a phenyl group. R 2 and R 3 may be the same or different. R 2 and R 3 may be bonded to each other to form a 3- to 7-membered ring. R 4 teeth, (c1) a hydrogen atom; (c2) (C 1 -C 6 ) alkyl group; (c3) (C 3 -C 6 ) cycloalkyl group; (c4) (C 1 -C 6 ) an alkoxy group; or (c5) (C 1 -C 6 ) represents an alkylcarbonyl group. R 5 teeth, (d1) (C 1 -C 6 ) alkyl group; (d2) (C 2 -C 6 ) alkenyl group; (d3) (C 2 -C 6 ) alkynyl group; (d4) (C 3 -C 6 ) cycloalkyl group; (d5) halo (C 1 -C 6 ) alkyl group; (d6) halo (C 2 -C 6 ) alkenyl group; (d7) halo (C 2 -C 6 ) an alkynyl group; (d8) a cyano group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) an alkoxy group, (C 1 -C 6 ) alkylthio group, halo(C 3 -C 6 ) cycloalkyl group, halo(C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) alkylthio group, carboxamide group, phenylcarbonyl group and di(C 1 -C 6 ) substituted (C) alkylamino groups each having 1 to 3 substituents independently selected from the group consisting of 1 -C 6 ) alkyl group; (d9) cyano group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) an alkoxy group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkyl group, halo (C 3 -C 6 ) cycloalkyl group, halo(C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) a substituted (C) alkylthio group and a carboxamide group, each of which has 1 to 3 substituents independently selected from the group consisting of an alkylthio group and a carboxamide group on the ring; 3 -C 6 ) cycloalkyl group; (d10) (C 1 -C 6 ) alkylsulfonyl group; (d11) N—(C 1 -C 6 ) alkylaminosulfonyl group; (d12) phenylcarbonylamino group; (d13) halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d14) a piperidinyl group; (d15) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group, halo (C 1 -C 6 ) an alkoxy group, (C 1 -C 6 ) alkoxycarbonyl group and phenyl (C 1 -C 6 (d16) a morpholinyl group; (d17) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d18) a substituted morpholinyl group having on the ring 1 to 3 substituents independently selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a hydroxyl group, (e) a carboxyl group, (f) a (C 1 -C 6 ) alkyl group, (g) (C 1 -C 6 ) alkoxy group, (h) (C 3 -C 6 ) cycloalkyl group, (i) (C 1 -C 6 ) alkylthio group, (j) (C 1 -C 6 ) alkylsulfinyl group, (k) (C 1 -C 6 ) alkylsulfonyl group, (l) halo(C 1 -C 6 ) alkyl group, (m) halo (C 1 -C 6 ) alkoxy group, (n) halo (C 3 -C 6 ) cycloalkyl group, (o) halo (C 1 -C 6 ) alkylthio group, (p) halo (C 1 -C 6 ) alkylsulfinyl group, (q) halo (C 1 -C 6 ) alkylsulfonyl group, (r) (C 1 -C 6 ) alkoxycarbonyl group, (s) (C 1 -C 6 ) alkylcarbonylamino group, (t) halo (C 1 -C 6 ) alkylcarbonylamino group, (u) (C 1 -C 6 ) alkylsulfonylamino group, (v) halo(C 1 -C 6 ) alkylsulfonylamino group, (w) N,N-di(C 1 -C 6 ) alkylcarboxamide group, (x) N-halo (C 1 -C 6 ) alkylcarboxamide group, (y) (C 1 -C 6 ) alkylcarbonyl group, (z) (C 1 -C 6 ) Alkylaminosulfonate Nyl group, (aa) SF 5 group, (ab) R 12 - (R 13 -N=)S group (in the formula, R 12 is (C 1 -C 6 ) alkyl group, (C 3 -C 6 ) cycloalkyl group, halo(C 1 -C 6 ) alkyl group, or (C 1 -C 6 ) alkoxy(C 1 -C 6 ) represents an alkyl group, and R 13 represents a hydrogen atom, a cyano group, (C 1 -C 6 ) alkyl group, (C 3 -C 6 ) cycloalkyl group, halo(C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkylcarbonyl group, or halo(C 1 -C 6 ) represents an alkylcarbonyl group. 12 - (R 13 -N=)O=S group (in the formula, R 12 and R 13 is the same as above.), (ad) a pyrazolyl group, (ae) a phenoxy group, (af) a phenyl group, and (ag) a halogen atom, a cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (a) a substituted phenyl group having on its ring 1 to 5 substituents independently selected from the group consisting of a halogen atom, a phenyl group, and (C) an alkoxy group; or (b) a substituted phenyl group having on its ring 1 to 5 substituents independently selected from the group consisting of a halogen atom, a phenyl group, and (C) an alkoxy group; 1 -C 6 a substituted phenyl group having on the ring a methylenedioxy group which may be substituted by 1 to 2 substituents selected from the group consisting of alkyl groups (provided that the atom adjacent to the bonding atom of the pyrazolyl group does not have a substituent selected from the group consisting of (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkylsulfonyl group and R 12 - (R 13 -N=)O=S group (in the formula, R 12 and R 13 is the same as above.) is not substituted.); (d20) a pyridyl group; (d21) a halogen atom, a cyano group, a nitro group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group, halo (C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) alkylthio group, halo(C 1 -C 6 ) alkylsulfinyl group and halo(C 1 -C 6 (d22) a N-oxo-pyridyl group; (d23) a halogen atom, a cyano group, a nitro group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group, halo (C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) alkylthio group, halo(C 1 -C 6 ) alkylsulfinyl group and halo(C 1 -C 6 (d24) a pyridazinyl group; (d25) a halogen atom, a cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d26) a pyrimidinyl group; (d27) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d28) a pyrazinyl group; (d29) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d30) a substituted pyrazinyl group having 1 to 3 substituents independently selected from the group consisting of alkoxy groups; (d31) a triazinyl group; A halogen atom, a cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d32) a tetrahydrofuranyl group; (d33) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d34) an oxazolinyl group; (d35) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d36) a thiazolinyl group; (d37) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d38) an oxazolyl group; (d39) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d40) a thiazolyl group; (d41) a halogen atom, a cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d42) an isoxazolyl group; (d43) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d44) an isothiazolyl group; (d45) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d46) an imidazolyl group; (d47) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d48) a pyrazolyl group; (d49) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d50) a triazolyl group; (d51) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d52) a tetrazolyl group; (d53) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d54) a substituted tetrazolyl group having one substituent on the ring selected from the group consisting of an alkoxy group; (d55) a halogen atom, a cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d56) a quinolinyl group; (d57) a halogen atom, a cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d58) a benzoxazolyl group; (d59) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d60) a benzothiazolyl group; (d61) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d62) a benzimidazolyl group; (d63) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d64) a benzothiadiazolyl group; (d65) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 ) a substituted benzothiazide having 1 to 4 substituents on the ring, each independently selected from the group consisting of an alkoxy group; an azolyl group; (d66) an indazolyl group; (d67) a halogen atom, a cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d68) an indanyl group; (d69) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d70) a tetrahydronaphthyl group; (d71) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d72) a substituted tetrahydronaphthyl group having 1 to 4 substituents independently selected from the group consisting of tetrahydrofuranyl (C 1 -C 6 ) alkyl group; (d73) halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 ) substituted tetrahydrofuranyl (C) having 1 to 3 substituents on the ring independently selected from the group consisting of alkoxy groups; 1 -C 6 ) alkyl group; (d74) phenyl (C 1 -C 6 ) alkyl group; (d75) halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 ) substituted phenyl (C) having 1 to 3 substituents on the ring independently selected from the group consisting of alkoxy groups; 1 -C 6 ) alkyl group; (d76) thienyl group; (d77) halogen atom, cyano group, nitro group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group, halo (C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) alkylthio group, halo(C 1 -C 6 ) alkylsulfinyl group and halo(C 1 -C 6 (d78) a naphthyl group; or (d79) a halogen atom, a cyano group, a nitro group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group, halo (C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) alkylthio group, halo(C 1 -C 6 ) alkylsulfinyl group and halo(C 1 -C 6 ) a substituted naphthyl group having on the ring 1 to 3 substituents independently selected from the group consisting of alkylsulfonyl groups; Q is, (e1) a substituted phenyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e2) a naphthyl group; (e3) a substituted naphthyl group having 1 to 7 substituents each independently selected from substituent group A on the ring; (e4) a substituted pyridyl group having 1 to 4 substituents each independently selected from substituent group A on the ring; (e5) a pyridazinyl group; (e6) a substituted pyridazinyl group having 1 to 3 substituents each independently selected from substituent group A on the ring; (e7) a pyrimidinyl group; (e8) a substituted pyrimidinyl group having 1 to 3 substituents each independently selected from substituent group A on the ring; (e9) a pyrazinyl group; (e10) a substituted pyrazinyl group having 1 to 3 substituents each independently selected from substituent group A on the ring; (e11) a triazinyl group; (e12) (e13) a substituted triazinyl group having on the ring one to two substituents each independently selected from substituent group A; (e14) a substituted 2-oxopyridyl group having on the ring one to four substituents each independently selected from substituent group A; (e15) a furyl group; (e16) a substituted furyl group having on the ring one to three substituents each independently selected from substituent group A; (e17) an isoxazolyl group; (e18) a substituted isoxazolyl group having on the ring one to two substituents each independently selected from substituent group A; (e19) an oxazolyl group; (e20) a substituted oxazolyl group having on the ring one to two substituents each independently selected from substituent group A; (e21) a thienyl group; (e22) a substituted thienyl group having on the ring one to three substituents each independently selected from substituent group A; (e23) an isothiazolyl group; (e24) a substituted isothiazolyl group having one to two substituents independently selected from the substituent group A on the ring; (e25) a thiazolyl group; (e26) a substituted thiazolyl group having one to two substituents independently selected from the substituent group A on the ring; (e27) an oxadiazolyl group; (e28) a substituted oxadiazolyl group having one substituent independently selected from the substituent group A on the ring; (e29) a thiadiazolyl group; (e30) a substituted thiadiazolyl group having one substituent independently selected from the substituent group A on the ring;(e31) a pyrrolyl group; (e32) a substituted pyrrolyl group having on the ring one to four substituents each independently selected from substituent group A; (e33) a pyrazolyl group; (e34) a substituted pyrazolyl group having on the ring one to three substituents each independently selected from substituent group A; (e35) an imidazolyl group; (e36) a substituted imidazolyl group having on the ring one to three substituents each independently selected from substituent group A; (e37) a triazolyl group; (e38) a substituted triazolyl group having on the ring one to two substituents each independently selected from substituent group A; (e39) a tetrazolyl group; (e40) a substituted tetrazolyl group having on the ring one substituent each independently selected from substituent group A; (e41) a benzofuranyl group; (e42) A substituted benzofuranyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e43) a benzoxazolyl group; (e44) a substituted benzoxazolyl group having 1 to 4 substituents each independently selected from substituent group A on the ring; (e45) a benzisoxazolyl group; (e46) a substituted benzoisoxazolyl group having 1 to 4 substituents each independently selected from substituent group A on the ring; (e47) a benzothienyl group; (e48) a substituted benzothienyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e49) a benzothiazolyl group; (e50) a substituted benzothiazolyl group having 1 to 4 substituents each independently selected from substituent group A on the ring; (e51) a benzisothiazolyl group; (e52) a substituted benzisothiazolyl group having 1 to 4 substituents each independently selected from substituent group A on the ring; (e53) an indolyl group; (e54) a substituted indolyl group having 1 to 6 substituents each independently selected from substituent group A on the ring; (e55) an isoindolyl group; (e56) a substituted isoindolyl group having 1 to 6 substituents each independently selected from substituent group A on the ring; (e57) an indazolyl group; (e58) a substituted indazolyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e59) a benzimidazolyl group;(e60) a substituted benzimidazolyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e61) a benzotriazolyl group; (e62) a substituted benzotriazolyl group having 1 to 4 substituents each independently selected from substituent group A on the ring; (e63) a furopyridyl group; (e64) a substituted furopyridyl group having 1 to 4 substituents each independently selected from substituent group A on the ring; (e65) a thienopyridyl group; (e66) a substituted thienopyridyl group having 1 to 4 substituents each independently selected from substituent group A on the ring; (e67) an indolizinyl group; (e68) a substituted indolizinyl group having 1 to 6 substituents each independently selected from substituent group A on the ring; (e69) a pyrrolopyridyl group; (e70) a substituted pyrrolopyridyl group having on the ring one to five substituents each independently selected from substituent group A; (e71) a pyrrolopyrimidinyl group; (e72) a substituted pyrrolopyrimidinyl group having on the ring one to five substituents each independently selected from substituent group A; (e73) an oxazolopyridyl group; (e74) a substituted oxazolopyridyl group having on the ring one to three substituents each independently selected from substituent group A; (e75) an isoxazolopyridyl group; (e76) a substituted isoxazolopyridyl group having on the ring one to three substituents each independently selected from substituent group A; (e77) a thiazolopyridyl group; (e78) a substituted thiazolopyridyl group having on the ring one to three substituents each independently selected from substituent group A; (e79) an isothiazolopyridyl group; (e80) a substituted isothiazolopyridyl group having 1 to 3 substituents each independently selected from substituent group A on the ring; (e81) an imidazopyridyl group; (e82) a substituted imidazopyridyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e83) an imidazopyrimidinyl group; (e84) a substituted imidazopyrimidinyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e85) a pyrazolopyridyl group; (e86) a substituted pyrazolopyridyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e87) a pyrazolopyrimidinyl group;(e88) a substituted pyrazolopyrimidinyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e89) a triazolopyridyl group; (e90) a substituted triazolopyridyl group having 1 to 4 substituents each independently selected from substituent group A on the ring; (e91) a triazolopyrimidinyl group; (e92) a substituted triazolopyrimidinyl group having 1 to 4 substituents each independently selected from substituent group A on the ring; (e93) a quinoxalinyl group; (e94) a substituted quinoxalinyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e95) a quinolinyl group; (e96) a substituted quinolinyl group having 1 to 6 substituents each independently selected from substituent group A on the ring; (e97) an isoquinolinyl group; (e98) a substituted isoquinolinyl group having 1 to 6 substituents each independently selected from substituent group A on the ring; (e99) a cinnolinyl group; (e100) a substituted cinnolinyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e101) a phthalazinyl group; (e102) a substituted phthalazinyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e103) a quinazolinyl group; (e104) a substituted quinazolinyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e105) a naphthyridinyl group; or (e106) a substituted naphthyridinyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; However, Q has a bond to the atom adjacent to the bond atom to the dihydropyran ring (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkylsulfonyl group, N—(C 1 -C 6 ) alkylaminosulfonyl group, N,N-di(C 1 -C 6 ) alkylaminosulfonyl group, and R 10 - (R 11 -N=)O=S group (in the formula, R 10 is (C 1 -C 6 ) alkyl group, (C 3 -C 6 ) cycloalkyl group, halo(C 1 -C 6 ) alkyl group, or (C 1 -C 6 ) alkoxy(C 1 -C 6 ) represents an alkyl group, and R 11 represents a hydrogen atom, a cyano group, (C 1 -C 6 ) alkyl group, (C 3 -C 6 ) cycloalkyl group, halo(C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkylcarbonyl group, or halo(C 1 -C 6 ) denotes an alkylcarbonyl group. ) is unsubstituted. X and Y each independently represent an oxygen atom or a sulfur atom. Z is OR 6 group (in the formula, R 6 is a hydrogen atom, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkylcarbonyl group or (C 1 -C 6 ) represents an alkoxycarbonyl group. ) S(O)nR 7 group (wherein n represents 0, 1 or 2, and R 7 is a hydrogen atom or (C 1 -C 6 ) represents an alkyl group. ) or N(R 8 ) R 9 group (in the formula, R 8 and R 9 is a hydrogen atom, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkylcarbonyl group or (C 1 -C 6 ) represents an alkoxycarbonyl group, and R 8 and R 9 may be the same or different. Substituent group A is (f1) a halogen atom; (f2) a cyano group; (f3) a nitro group; (f4) a hydroxyl group; (f5) a carboxyl group; (f6) (C 1 -C 6 ) alkyl group; (f7) (C 2 -C 6 ) alkenyl group; (f8) (C 2 -C 6 ) alkynyl group; (f9) (C 1 -C 6 ) alkoxy group; (f10) (C 3 -C 6 ) cycloalkyl group; (f11) a halogen atom, a cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxy group and (C 1 -C 6 ) a substituted (C) alkylcarbonyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of 3 -C 6 ) cycloalkyl group; (f12) (C 1 -C 6 ) alkoxy(C 1 -C 6 ) alkyl group; (f13) (C 1 -C 6 ) alkylthio group; (f14) (C 1 -C 6 ) alkylsulfinyl group; (f15) (C 1 -C 6 ) alkylsulfonyl group; (f16) halo (C 1 -C 6 ) alkyl group; (f17) halo (C 2 -C 6 ) alkenyl group; (f18) halo (C 2 -C 6 ) alkynyl group; (f19) halo (C 1 -C 6 ) alkoxy group; (f20) halo (C 3 -C 6 ) cycloalkyl group; (f21) halo (C 1 -C 6 ) alkylthio group; (f22) halo (C 1 -C 6 ) alkylsulfinyl group; (f23) halo (C 1 -C 6 ) alkylsulfonyl group; (f24) SF 5 Group; (f25) (C 1 -C 6 ) alkylcarbonylamino group; (f26) halo (C 1 -C 6 ) alkylcarbonylamino group; (f27) (C 1 -C 6 ) alkylsulfonylamino group; (f28) halo(C 1 -C 6 ) alkylsulfonylamino group; (f29) N,N-di(C 1 -C 6 ) alkylcarboxamide group; (f30) N-halo (C 1 -C 6 ) alkylcarboxamide group; (f31) (C 1 -C 6 ) alkoxycarbonyl group; (f32) N—(C 1 -C 6 ) alkylaminosulfonyl group; (f33) N,N-di(C 1 -C 6 ) alkylaminosulfonyl group; (f34) pyrazolyl group; (f35) halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (f36) an oxadiazolyl group; (f37) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (f38) a phenyl group; (f39) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (f40) a phenoxy group; (f41) a halogen atom, a phenyl group, and (C) an alkoxy group formed by two adjacent substituents taken together; 1 -C 6 (f42) R 10 - (R 11 -N=)O=S group (in the formula, R 10 is (C 1 -C 6 ) alkyl group, (C 3 -C 6 ) cycloalkyl group, halo(C 1 -C 6 ) alkyl group, or (C 1 -C 6 ) alkoxy(C 1 -C 6 ) represents an alkyl group, and R 11 represents a hydrogen atom, a cyano group, (C 1 -C 6 ) alkyl group, (C 3 -C 6 ) cycloalkyl group, halo(C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkylcarbonyl group, or halo(C 1 -C 6 ) represents an alkylcarbonyl group. ) ; (f43) R 10 - (R 11 -N=)S group (in the formula, R 10 and R 11 is the same as above; (f44) a halogen atom, a cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (f45) a substituted phenoxy group having 1 to 5 substituents on the ring independently selected from the group consisting of N,N-di(C 1 -C 6 ) alkylamino group; (f46) (C 1 -C 6 ) alkylcarbonyl group; and (f47) N—(C 1 -C 6 ) an alkylcarboxamide group, or a salt thereof.

2. R 1 but, (a1) a hydrogen atom; or (a2) (C 1 -C 6 ) alkyl group, R 2 and R 3 but, (b1) a hydrogen atom; (b2) (C 1 -C 6 ) alkyl group; (b3) (C 1 -C 6 ) alkoxy(C 1 -C 6 ) alkyl group; (b4) N-(C 1 -C 6 ) alkylamino (C 1 -C 6 ) alkyl group; or (b5) (C 1 -C 6 ) alkoxycarbonylamino (C 1 -C 6 ) alkyl group, R 2 and R 3 may be the same or different, R 2 and R 3 may be bonded to each other to form a 3- to 7-membered ring, R 4 but, (c1) a hydrogen atom; (c2) (C 1 -C 6 ) alkyl group; or (c3) (C 3 -C 6 ) a cycloalkyl group; R 5 but, (d1) (C 1 -C 6 ) alkyl group; (d2) (C 2 -C 6 ) alkenyl group; (d3) (C 2 -C 6 ) alkynyl group; (d4) (C 3 -C 6 ) cycloalkyl group; (d5) halo (C 1 -C 6 ) alkyl group; (d8) cyano group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) an alkoxy group, (C 1 -C 6 ) alkylthio group, halo(C 3 -C 6 ) cycloalkyl group, halo(C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) alkylthio group, carboxamide group, phenylcarbonyl group and di(C 1 -C 6 ) substituted (C) alkylamino groups each having 1 to 3 substituents independently selected from the group consisting of 1 -C 6 ) alkyl group; (d9) cyano group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) an alkoxy group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkyl group, halo (C 3 -C 6 ) cycloalkyl group, halo(C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) a substituted (C) alkylthio group and a carboxamide group, each of which has 1 to 3 substituents independently selected from the group consisting of an alkylthio group and a carboxamide group on the ring; 3 -C 6 ) cycloalkyl group; (d18) phenyl group; (d19) (a) halogen atom, (b) cyano group, (c) nitro group, (d) hydroxyl group, (e) carboxyl group, (f) (C 1 -C 6 ) alkyl group, (g) (C 1 -C 6 ) alkoxy group, (h) (C 3 -C 6 ) cycloalkyl group, (i) (C 1 -C 6 ) alkylthio group, (j) (C 1 -C 6 ) alkylsulfinyl group, (k) (C 1 -C 6 ) alkylsulfonyl group, (l) halo(C 1 -C 6 ) alkyl group, (m) halo (C 1 -C 6 ) alkoxy group, (n) halo (C 3 -C 6 ) cycloalkyl group, (o) halo (C 1 -C 6 ) alkylthio group, (p) halo (C 1 -C 6 ) alkylsulfinyl group, (q) halo (C 1 -C 6 ) alkylsulfonyl group, (r) (C 1 -C 6 ) alkoxycarbonyl group, (s) (C 1 -C 6 ) alkylcarbonylamino group, (t) halo (C 1 -C 6 ) alkylcarbonylamino group, (u) (C 1 -C 6 ) alkylsulfonylamino group, (v) halo(C 1 -C 6 ) alkylsulfonylamino group, (w) N,N-di(C 1 -C 6 ) alkylcarboxamide group, (x) N-halo (C 1 -C 6 ) alkylcarboxamide group, (y) (C 1 -C 6 ) alkylcarbonyl group, (z) (C 1 -C 6 ) alkylaminosulfonyl group, (aa) SF 5 group, (ab) R 12 - (R 13 -N=)S group (in the formula, R 12 is (C 1 -C 6 ) alkyl group, (C 3 -C 6 ) cycloalkyl group, halo(C 1 -C 6 ) alkyl group, or (C 1 -C 6 ) alkoxy(C 1 -C 6 ) represents an alkyl group, and R 13 represents a hydrogen atom, a cyano group, (C 1 -C 6 ) alkyl group, (C 3 -C 6 ) cycloalkyl group, halo(C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkylcarbonyl group, or halo(C 1 -C 6 ) represents an alkylcarbonyl group. 12 - (R 13 -N=)O=S group (in the formula, R 12 and R 13 is the same as above.), (ad) a pyrazolyl group, (ae) a phenoxy group, (af) a phenyl group, and (ag) a halogen atom, a cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (a) a substituted phenyl group having on its ring 1 to 5 substituents independently selected from the group consisting of a halogen atom, a phenyl group, and (C) an alkoxy group; or (b) a substituted phenyl group having on its ring 1 to 5 substituents independently selected from the group consisting of a halogen atom, a phenyl group, and (C) an alkoxy group; 1 -C 6 a substituted phenyl group having on the ring a methylenedioxy group which may be substituted by 1 to 2 substituents selected from the group consisting of alkyl groups (provided that the atom adjacent to the bonding atom of the pyrazolyl group does not have a substituent selected from the group consisting of (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkylsulfonyl group and R 12 - (R 13 -N=)O=S group (in the formula, R 12 and R 13 is the same as above.) is not substituted.); (d20) a pyridyl group; (d21) a halogen atom, a cyano group, a nitro group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group, halo (C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) alkylthio group, halo(C 1 -C 6 ) alkylsulfinyl group and halo(C 1 -C 6 (d24) a pyridazinyl group; (d25) a halogen atom, a cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d26) a pyrimidinyl group; (d27) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d28) a pyrazinyl group; (d29) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d30) a triazinyl group; (d31) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d38) an oxazolyl group; (d39) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d40) a thiazolyl group; (d41) a halogen atom, a cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d42) an isoxazolyl group; (d43) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d48) a pyrazolyl group; (d49) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d50) a triazolyl group; (d51) a halogen atom, a cyano group; , (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d52) a tetrazolyl group; (d53) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d54) a substituted tetrazolyl group having one substituent on the ring selected from the group consisting of an alkoxy group; (d55) a halogen atom, a cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d56) a quinolinyl group; (d57) a halogen atom, a cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d60) a benzothiazolyl group; (d61) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d62) a benzimidazolyl group; (d63) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d68) an indanyl group; (d69) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d70) a tetrahydronaphthyl group; (d71) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (d74) a substituted tetrahydronaphthyl group having 1 to 4 substituents on the ring independently selected from the group consisting of phenyl (C 1 -C 6 ) alkyl group; (d75) halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 ) substituted phenyl (C) having 1 to 3 substituents on the ring independently selected from the group consisting of alkoxy groups; 1 -C 6 ) alkyl group; (d76) thienyl group; (d77) halogen atom, cyano group, nitro group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group, halo (C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) alkylthio group, halo(C 1 -C 6 ) alkylsulfinyl group and halo(C 1 -C 6 (d78) a naphthyl group; or (d79) a halogen atom, a cyano group, a nitro group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group, halo (C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) alkylthio group, halo(C 1 -C 6 ) alkylsulfinyl group and halo(C 1 -C 6 a substituted naphthyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of alkylsulfonyl groups; Q is, (e1) a substituted phenyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e2) a naphthyl group; (e3) a substituted naphthyl group having 1 to 7 substituents each independently selected from substituent group A on the ring; (e4) a substituted pyridyl group having 1 to 4 substituents each independently selected from substituent group A on the ring; (e5) a pyridazinyl group; (e6) a substituted pyridazinyl group having 1 to 3 substituents each independently selected from substituent group A on the ring; (e7) a pyrimidinyl group; (e8) a substituted pyrimidinyl group having 1 to 3 substituents each independently selected from substituent group A on the ring; (e9) a pyrazinyl group; (e10) a substituted pyrazinyl group having 1 to 3 substituents each independently selected from substituent group A on the ring; (e11) a triazinyl group; (e12) (e17) a substituted triazinyl group having on the ring one to two substituents each independently selected from substituent group A; (e18) a substituted isoxazolyl group having on the ring one to two substituents each independently selected from substituent group A; (e19) an oxazolyl group; (e20) a substituted oxazolyl group having on the ring one to two substituents each independently selected from substituent group A; (e21) a thienyl group; (e22) a substituted thienyl group having on the ring one to three substituents each independently selected from substituent group A; (e23) an isothiazolyl group; (e24) a substituted isothiazolyl group having on the ring one to two substituents each independently selected from substituent group A; (e25) a thiazolyl group; (e26) a substituted thiazolyl group having on the ring one to two substituents each independently selected from substituent group A; (e41) a benzofuranyl group; (e42) a substituted benzofuranyl group having 1 to 5 substituents independently selected from the substituent group A on the ring; (e43) a benzoxazolyl group; (e44) a substituted benzoxazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (e45) a benzoisoxazolyl group; (e46) a substituted benzoisoxazolyl group having 1 to 4 substituents independently selected from the substituent group A on the ring; (e47) a benzothienyl group;(e48) a substituted benzothienyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e49) a benzothiazolyl group; (e50) a substituted benzothiazolyl group having 1 to 4 substituents each independently selected from substituent group A on the ring; (e51) a benzoisothiazolyl group; (e52) a substituted benzoisothiazolyl group having 1 to 4 substituents each independently selected from substituent group A on the ring; (e53) an indolyl group; (e54) a substituted indolyl group having 1 to 6 substituents each independently selected from substituent group A on the ring; (e55) an isoindolyl group; (e56) a substituted isoindolyl group having 1 to 6 substituents each independently selected from substituent group A on the ring; (e57) an indazolyl group; (e58) a substituted indazolyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e59) a benzimidazolyl group; (e60) a substituted benzimidazolyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e61) a benzotriazolyl group; (e62) a substituted benzotriazolyl group having 1 to 4 substituents each independently selected from substituent group A on the ring; (e65) a thienopyridyl group; (e66) a substituted thienopyridyl group having 1 to 4 substituents each independently selected from substituent group A on the ring; (e67) an indolizinyl group; (e68) a substituted indolizinyl group having 1 to 6 substituents each independently selected from substituent group A on the ring; (e69) a pyrrolopyridyl group; (e70) a substituted pyrrolopyridyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e71) a pyrrolopyrimidinyl group; (e72) a substituted pyrrolopyrimidinyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e77) a thiazolopyridyl group; (e78) a substituted thiazolopyridyl group having 1 to 3 substituents each independently selected from substituent group A on the ring; (e79) an isothiazolopyridyl group; (e80) a substituted isothiazolopyridyl group having 1 to 3 substituents each independently selected from substituent group A on the ring; (e93) a quinoxalinyl group;(e94) a substituted quinoxalinyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e95) a quinolinyl group; (e96) a substituted quinolinyl group having 1 to 6 substituents each independently selected from substituent group A on the ring; (e97) an isoquinolinyl group; (e98) a substituted isoquinolinyl group having 1 to 6 substituents each independently selected from substituent group A on the ring; (e99) a cinnolinyl group; (e100) a substituted cinnolinyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e101) a phthalazinyl group; (e102) a substituted phthalazinyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e103) a quinazolinyl group; (e104) a substituted quinazolinyl group having 1 to 5 substituents independently selected from Substituent Group A on the ring; (e105) a naphthyridinyl group; or (e106) a substituted naphthyridinyl group having 1 to 5 substituents independently selected from Substituent Group A on the ring; X and Y are each independently an oxygen atom or a sulfur atom; Z is OR 6 group (in the formula, R 6 is a hydrogen atom, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkylcarbonyl group or (C 1 -C 6 ) represents an alkoxycarbonyl group. ) or S(O)nR 7 group (wherein n represents 0, 1 or 2, and R 7 is a hydrogen atom or (C 1 -C 6 ) represents an alkyl group; Substituent group A is (f1) a halogen atom; (f2) a cyano group; (f3) a nitro group; (f5) a carboxyl group; (f6) (C 1 -C 6 ) alkyl group; (f7) (C 2 -C 6 ) alkenyl group; (f8) (C 2 -C 6 ) alkynyl group; (f9) (C 1 -C 6 ) alkoxy group; (f10) (C 3 -C 6 ) cycloalkyl group; (f11) a halogen atom, a cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxy group and (C 1 -C 6 ) a substituted (C) alkylcarbonyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of 3 -C 6 ) cycloalkyl group; (f12) (C 1 -C 6 ) alkoxy(C 1 -C 6 ) alkyl group; (f13) (C 1 -C 6 ) alkylthio group; (f14) (C 1 -C 6 ) alkylsulfinyl group; (f15) (C 1 -C 6 ) alkylsulfonyl group; (f16) halo (C 1 -C 6 ) alkyl group; (f19) halo (C 1 -C 6 ) alkoxy group; (f20) halo (C 3 -C 6 ) cycloalkyl group; (f21) halo (C 1 -C 6 ) alkylthio group; (f22) halo (C 1 -C 6 ) alkylsulfinyl group; (f23) halo (C 1 -C 6 ) alkylsulfonyl group; (f24) SF 5 Group; (f25) (C 1 -C 6 ) alkylcarbonylamino group; (f26) halo (C 1 -C 6 ) alkylcarbonylamino group; (f27) (C 1 -C 6 ) alkylsulfonylamino group; (f28) halo(C 1 -C 6 ) alkylsulfonylamino group; (f29) N,N-di(C 1 -C 6 ) alkylcarboxamide group; (f30) N-halo (C 1 -C 6 ) alkylcarboxamide group; (f31) (C 1 -C 6 ) alkoxycarbonyl group; (f32) N—(C 1 -C 6 ) alkylaminosulfonyl group; (f34) pyrazolyl group; (f35) halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (f38) a phenyl group; (f39) a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (f40) a phenoxy group; (f41) a halogen atom, a phenyl group, and (C) an alkoxy group formed by two adjacent substituents taken together; 1 -C 6 (f42) R 10 - (R 11 -N=)O=S group (in the formula, R 10 is (C 1 -C 6 ) alkyl group, (C 3 -C 6 ) cycloalkyl group, halo(C 1 -C 6 ) alkyl group, or (C 1 -C 6 ) alkoxy(C 1 -C 6 ) represents an alkyl group, and R 11 represents a hydrogen atom, a cyano group, (C 1 -C 6 ) alkyl group, (C 3 -C 6 ) cycloalkyl group, halo(C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkylcarbonyl group, or halo(C 1 -C 6 ) represents an alkylcarbonyl group. ) ; (f43) R 10 - (R 11 -N=)S group (in the formula, R 10 and R 11 is the same as above; (f44) a halogen atom, a cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) an alkoxy group, (C 3 -C 6 ) a cycloalkyl group, (C 1 -C 6 ) alkylthio group, (C 1 -C 6 ) alkylsulfinyl group, (C 1 -C 6 ) alkylsulfonyl group, halo(C 1 -C 6 ) alkyl group and halo(C 1 -C 6 (f45) a substituted phenoxy group having 1 to 5 substituents on the ring independently selected from the group consisting of N,N-di(C 1 -C 6 ) alkylamino group; (f46) (C 1 -C 6 ) alkylcarbonyl group; and (f47) N—(C 1 -C 6 2. The compound or salt thereof according to claim 1, wherein the compound or salt comprises an alkylcarboxamide group.

3. R 1 (a1) is a hydrogen atom, R 2 and R 3 but, (b1) a hydrogen atom; (b2) (C 1 -C 6 ) alkyl group; or (b5) (C 1 -C 6 ) alkoxycarbonylamino (C 1 -C 6 ) alkyl group, R 2 and R 3 may be the same or different, R 2 and R 3 may be bonded to each other to form a 3- to 6-membered ring, R 4 is (c1) a hydrogen atom, R 5 but, (d4) (C 3 -C 6 ) cycloalkyl group; (d18) phenyl group; (d19') (a) halogen atom, (b) cyano group, (c) nitro group, (f) (C 1 -C 6 ) alkyl group, (g) (C 1 -C 6 ) alkoxy group, (h) (C 3 -C 6 ) cycloalkyl group, (i) (C 1 -C 6 ) alkylthio group, (j) (C 1 -C 6 ) alkylsulfinyl group, (k) (C 1 -C 6 ) alkylsulfonyl group, (l) halo(C 1 -C 6 ) alkyl group, (m) halo (C 1 -C 6 ) alkoxy group, (o) halo (C 1 -C 6 ) alkylthio group, (p) halo (C 1 -C 6 ) alkylsulfinyl group, (q) halo (C 1 -C 6 ) alkylsulfonyl group, (r) (C 1 -C 6 ) alkoxycarbonyl group, (s) (C 1 -C 6 ) alkylcarbonylamino group, (u) (C 1 -C 6 ) alkylsulfonylamino group, (x) N-halo (C 1 -C 6 ) alkylcarboxamide group, (y) (C 1 -C 6 ) alkylcarbonyl group, (z) (C 1 -C 6 ) alkylaminosulfonyl group, (aa) SF 5 (d20) a pyridyl group; (d21') a substituted pyridyl group having on the ring one to four substituents independently selected from halogen atoms; (d25') a substituted pyridazinyl group having on the ring one to three substituents independently selected from halogen atoms; (d27') a substituted pyrimidinyl group having on the ring one to three substituents independently selected from halogen atoms; (d29') a substituted pyrazinyl group having on the ring one to three substituents independently selected from halogen atoms; (d30) a triazinyl group; (d38) an oxazolyl group; (d40) a thiazolyl group; (d43') (C 1 -C 6 (d49') a substituted isoxazolyl group having on the ring 1 or 2 substituents independently selected from alkyl groups; (d49') (C 1 -C 6 (d50) a triazolyl group; (d52) a tetrazolyl group; (d55') a halo(C 1 -C 6 ) a substituted thiadiazolyl group having one substituent selected from alkyl groups on the ring; (d56) a quinolinyl group; (d60) a benzothiazolyl group; (d63') (C 1 -C 6 (d76) a substituted benzimidazolyl group having 1 to 4 substituents on the ring independently selected from alkyl groups; or (d77) a thienyl group; Q is, (e1) a substituted phenyl group having 1 to 5 substituents each independently selected from substituent group A on the ring; (e2) a naphthyl group; (e4) a substituted pyridyl group having 1 to 4 substituents each independently selected from substituent group A on the ring; (e18) a substituted isoxazolyl group having 1 to 2 substituents each independently selected from substituent group A on the ring; (e19) an oxazolyl group; or (e23) an isothiazolyl group; X and Y are each independently an oxygen atom or a sulfur atom; Z is OR 6 group (in the formula, R 6 represents a hydrogen atom. Substituent group A is (f1) a halogen atom; (f2) a cyano group; (f3) a nitro group; (f5) a carboxyl group; (f6) (C 1 -C 6 ) alkyl group; (f9) (C 1 -C 6 ) alkoxy group; (f13) (C 1 -C 6 ) alkylthio group; (f14) (C 1 -C 6 ) alkylsulfinyl group; (f15) (C 1 -C 6 ) alkylsulfonyl group; (f16) halo (C 1 -C 6 ) alkyl group; (f19) halo (C 1 -C 6 ) alkoxy group; (f21) halo (C 1 -C 6 ) alkylthio group; (f22) halo (C 1 -C 6 ) alkylsulfinyl group; (f30) N-halo (C 1 -C 6 ) alkylcarboxamide group; (f31) (C 1 -C 6 ) an alkoxycarbonyl group; (f38) a phenyl group; (f41') a methylenedioxy group formed by two adjacent substituents taken together; (f43') R 10 - (R 11 -N=)S group (in the formula, R 10 (C 1 -C 6 ) represents an alkyl group, and R 11 represents a cyano group; and (f44') a substituted phenoxy group having 1 to 5 cyano groups on the ring, or a salt thereof, according to claim 1 or 2.

4. A pesticide comprising the compound or salt thereof according to claim 1 or 2 as an active ingredient.

5. 3. An agricultural and horticultural pest control agent comprising the compound or salt thereof according to claim 1 or 2 as an active ingredient.

6. 3. An animal ectoparasite control agent, comprising the compound or salt thereof according to claim 1 or 2 as an active ingredient.

7. 3. An animal endoparasite control agent, comprising the compound or salt thereof according to claim 1 or 2 as an active ingredient.

8. A method for controlling agricultural and horticultural pests, which comprises applying an effective amount of the agricultural and horticultural pest control agent according to claim 5 to plants or soil.

9. A method for controlling ectoparasites in animals, comprising orally or parenterally administering an effective amount of the animal ectoparasite-controlling agent according to claim 6 to a target animal.

10. A method for controlling internal parasites in animals, comprising orally or parenterally administering an effective amount of the animal internal parasite control agent according to claim 7 to a target animal.

11. 3. Use of the compound or salt thereof according to claim 1 or 2 as a pest control agent.

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