JP2006008675A - Substituted pyrazinecarboxylic acid anilide derivative or salt thereof, intermediate thereof, agricultural/horticultural agent and use thereof - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide new agricultural/horticultural agents solving the problems that the developments of new agricultural/horticultural agents, especially agricultural/horticultural insecticides are desired since agricultural and horticultural crop productions are suffered from mach damages caused by noxious insects and noxious insects resisting to conventional agents appear, and various labor saving applications are desired since agricultural workers become older and the developments of agricultural/horticultural agents, especially agricultural/horticultural insecticides having suitable properties for such application methods are desired. <P>SOLUTION: The substituted pyrazinecarboxylic acid anilide derivative represented by formula (I) [wherein, R<SP>1</SP>is H, a halo 1-6C alkyl or the like; R<SP>2</SP>is H, a halogen, a 1-6C alkyl or the like; G is a 2-10C alkyl or the like; Z is O or S; X may be the same or different and is H, a halogen or the like; Y may be the same or different and is H, a halogen, cyano or the like; and m and n are each an integer of 1-3], salts thereof, agricultural/horticultural agents comprising the compound as the active component, intermediate compounds thereof and use thereof are provided. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to substituted pyrazine carboxylic acid anilide derivatives and salts thereof, intermediates thereof, agricultural and horticultural agents containing the compound as an active ingredient, in particular insecticides or acaricides, and methods of using the same.

Conventionally, it is known that substituted anilide derivatives similar to the present invention are useful as agricultural and horticultural insecticides, fungicides or acaricides (see, for example, Patent Document 1). There is no specific disclosure of the compounds of the present invention. In the heterocyclic carboxylic acid moiety, there is no example of the compound into which the pyrazine ring of the present invention is introduced, and it is not described in the compound list. Also, in the substituent of the aniline part, the example of the substituent at the 3-position is only a methyl group, and there is no example of a compound in which an alkyl group having 2 or more carbon atoms is introduced at the 3-position of the present invention. Not listed in the table. Furthermore, the 3-position methyl compound specifically disclosed therein does not show acaricidal activity.
JP 2003-48878 A

  In crop production such as agriculture and horticulture, damage caused by pests is still large, and development of new agricultural and horticultural drugs, especially insecticides or acaricides, is desired due to factors such as the generation of resistant pests resistant to existing drugs. Yes. Further, various labor-saving application methods are required due to the aging of farmers, and the creation of agricultural and horticultural agents, particularly insecticides or acaricides, having characteristics suitable for these application methods.

As a result of intensive studies to develop novel agricultural and horticultural agents, in particular, insecticides or acaricides, the present inventors have made pyrazine as a heterocyclic carboxylic acid moiety among a wide range of compounds described in the above-mentioned conventional literature. A substituted pyrazinecarboxylic acid anilide derivative represented by the general formula (I) of the present invention, in which a ring is selected and a specific substituent is introduced at the 3-position of the aniline portion, is described in the above-mentioned conventional literature as an acaricide. Found an excellent control effect that could not be expected at all. Furthermore, the substituted aniline derivative represented by the general formula (II) and the substituted pyrazinecarboxylic acid derivative represented by the general formula (III ′), which are intermediates of the compound, are novel compounds not described in any literature, The present invention has been completed by finding that it is an intermediate useful in the production of various derivatives having physiological activity such as pharmaceuticals and agricultural chemicals.

｛式中、Ｒ¹は水素原子、C₁-C₆アルキル基、ハロC₁-C₆アルキル基、C₁-C₆アルキルカルボニル基、ハロC₁-C₆アルキルカルボニル基、C₁-C₆アルキルカルボニルC₁-C₆アルキル基、シクロC₃-C₆アルキル基、ハロシクロC₃-C₆アルキル基、シクロC₃-C₆アルキルC₁-C₆アルキル基、ハロシクロC₃-C₆アルキルC₁-C₆アルキル基、C₂-C₆アルケニル基、ハロC₂-C₆アルケニル基、C₂-C₆アルキニル基、ハロC₂-C₆アルキニル基、C₁-C₆アルコキシC₁-C₆アルキル基、ハロC₁-C₆アルコキシC₁-C₆アルキル基、C₁-C₆アルコキシC₁-C₆アルコキシC₁-C₆アルキル基、C₁-C₆アルキルチオC₁-C₆アルキル基、ハロC₁-C₆アルキルチオC₁-C₆アルキル基、C₁-C₆アルキルスルフィニルC₁-C₆アルキル基、ハロC₁-C₆アルキルスルフィニルC₁-C₆アルキル基、C₁-C₆アルキルスルホニルC₁-C₆アルキル基、ハロC₁-C₆アルキルスルホニルC₁-C₆アルキル基、モノC₁-C₆アルキルアミノC₁-C₆アルキル基、同一又は異なっても良いジC₁-C₆アルキルアミノC₁-C₆アルキル基、フェニルC₁-C₆アルコキシC₁-C₆アルキル基、C₁-C₆アルコキシカルボニル基、C₁-C₆アルコキシC₁-C₆アルコキシカルボニル基、ハロC₁-C₆アルコキシカルボニル基、C₁-C₆アルキルチオカルボニル基、モノC₁-C₆アルキルアミノカルボニル基、同一又は異なっても良いジC₁-C₆アルキルアミノカルボニル基、C₁-C₆アルコキシカルボニルC₁-C₆アルキル基、C₁-C₆アルキルスルホニル基、ハロC₁-C₆アルキルスルホニル基、シアノC₁-C₆アルキル基、 That is, the present invention relates to the general formula (I)

{Wherein R ¹ is a hydrogen atom, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkylcarbonyl group, a halo C ₁ -C ₆ alkylcarbonyl group, C ₁ -C ₆ alkylcarbonyl C ₁ -C ₆ alkyl group, cyclo C ₃ -C ₆ alkyl group, halocyclo C ₃ -C ₆ alkyl group, cyclo C ₃ -C ₆ alkyl C ₁ -C ₆ alkyl group, halocyclo C ₃ -C ₆ Alkyl C ₁ -C ₆ alkyl group, C ₂ -C ₆ alkenyl group, halo C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, halo C ₂ -C ₆ alkynyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkyl sulfinyl C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl sulfinyl C ₁ -C ₆ alkyl group group, C ₁ -C ₆ alkyl Sulfonyl C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkylsulfonyl C ₁ -C ₆ alkyl group, mono-C ₁ -C ₆ alkylamino C ₁ -C ₆ alkyl group, the same or different and may di C ₁ -C ₆ alkylamino C ₁ -C ₆ alkyl group, phenyl C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxycarbonyl group, halo C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkyl thio group, mono C ₁ -C ₆ alkylaminocarbonyl group, the same or different di C ₁ may be -C ₆ alkylaminocarbonyl groups, C ₁ -C ₆ alkoxycarbonyl C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, a cyano C ₁ -C ₆ alkyl group,

Phenyl C ₁ -C ₆ alkyl group, which may be the same or different, halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, Halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ Selected from alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di-C ₁ -C ₆ alkylamino group which may be the same or different or C ₁ -C ₆ alkoxycarbonyl group A substituted phenyl C ₁ -C ₆ alkyl group having one or more substituents on the ring, a phenoxycarbonyl group, which may be the same or different, a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy Group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ One or more substituents selected from a —C ₆ alkylsulfonyl group, a mono C ₁ -C ₆ alkylamino group, a di C ₁ -C ₆ alkylamino group or a C ₁ -C ₆ alkoxycarbonyl group which may be the same or different; Substituted phenoxycarbonyl group, phenylsulfonyl group, which may be the same or different, halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ - C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl , Mono C ₁ -C ₆ alkylamino group, the same or different and may di C ₁ -C ₆ alkylamino group or a C ₁ -C ₆ alkoxy-substituted phenylsulfonyl group having one or more substituents selected from the group , same or different good di C ₁ -C ₆ alkyl phosphono group, the same or different di C ₁ may be -C ₆ Alkylphosphonothioate group, NC ₁ -C ₆ alkyl -NC ₁ -C ₆ alkoxycarbonylamino thio, NC ₁ -C ₆ alkyl -NC ₁ -C ₆ alkoxycarbonyl C ₁ -C ₆ alkylamino thio group, the same or different and may di C ₁ -C ₆ alkylamino thio group or a cycloalkyl C ₃ -C, _{6 represents} an alkylcarbonyl group.

R ² is a hydrogen atom, halogen atom, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, cyano group, hydroxy group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkoxy C ₁ -C ₃ alkoxy group, halo C ₁ -C ₆ alkoxy C ₁ -C ₃ alkoxy groups, C ₁ -C ₆ alkylthio C ₁ -C ₃ alkoxy group, halo C ₁ -C ₆ alkylthio C ₁ -C ₃ alkoxy groups, C ₁ -C ₆ alkylsulfinyl C ₁ -C ₃ alkoxy group, halo C ₁ -C ₆ alkylsulfinyl C ₁ -C ₃ alkoxy groups, C ₁ -C ₆ alkylsulfonyl C ₁ -C ₃ Alkoxy group, halo C ₁ -C ₆ alkylsulfonyl C ₁ -C ₃ alkoxy group, mono C ₁ -C ₆ alkylamino C ₁ -C ₃ alkoxy group, di C ₁ -C ₆ alkylamino C which may be the same or different ₁ -C ₃ alkoxy groups, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkyl Sulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, amino group, mono C ₁ -C ₆ alkylamino group, di C ₁ -C ₆ alkylamino group which may be the same or different Phenoxy group, which may be the same or different, halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo One or more selected from a C ₁ -C ₆ alkylsulfonyl group, a mono C ₁ -C ₆ alkylamino group, a di C ₁ -C ₆ alkylamino group which may be the same or different, or a C ₁ -C ₆ alkoxycarbonyl group Substituted substituted phenoxy group, phenylthio group, the same or different Halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkyl Substituted phenylthio having one or more substituents selected from a sulfonyl group, a mono C ₁ -C ₆ alkylamino group, a di C ₁ -C ₆ alkylamino group or a C ₁ -C ₆ alkoxycarbonyl group which may be the same or different Group,

Phenylsulfinyl group, which may be identical or different, a halogen atom, a cyano group, a nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo One or more selected from a C ₁ -C ₆ alkylsulfonyl group, a mono C ₁ -C ₆ alkylamino group, a di C ₁ -C ₆ alkylamino group which may be the same or different, or a C ₁ -C ₆ alkoxycarbonyl group Substituted substituted phenylsulfinyl group, phenylsulfonyl group, which may be the same or different, halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ Alkylthio group, a halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, A substituted phenylsulfonyl group having one or more substituents selected from a mono C ₁ -C ₆ alkylamino group, a di C ₁ -C ₆ alkylamino group which may be the same or different, or a C ₁ -C ₆ alkoxycarbonyl group, A phenyl C ₁ -C ₆ alkoxy group, which may be the same or different, a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, Halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ Alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group Substituted on the ring with one or more substituents selected from a mono C ₁ -C ₆ alkylamino group, a di C ₁ -C ₆ alkylamino group which may be the same or different, or a C ₁ -C ₆ alkoxycarbonyl group A phenyl C ₁ -C ₆ alkoxy group;

G is a C ₂ -C ₁₀ alkyl group, a halo C ₂ -C ₁₀ alkyl group, a C ₃ -C ₁₀ alkenyl group, a halo C ₃ -C ₁₀ alkenyl group, a C ₃ -C ₁₀ alkynyl group, a halo C ₃ -C ₁₀ An alkynyl group, a C ₃ -C ₁₀ cycloalkyl group, which may be the same or different and has one or more substituents selected from a halogen atom, a C ₁ -C ₆ alkyl group or a halo C ₁ -C ₆ alkyl group C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, which may be the same or different, and one or more selected from a halogen atom, a C ₁ -C ₆ alkyl group or a halo C ₁ -C ₆ alkyl group A substituted C ₃ -C ₁₀ cycloalkenyl group, a C ₃ -C ₈ cycloalkyl C ₁ -C ₆ alkyl group or a halo C ₃ -C ₈ cycloalkyl C ₁ -C ₆ alkyl group having the following substituents:
Z represents an oxygen atom or a sulfur atom.
X may be the same or different and each represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group or a halo C ₁ -C ₆ alkyl group.

Y may be the same or different, and may be a hydrogen atom, halogen atom, cyano group, nitro group, hydroxyl group, mercapto group, amino group, carboxyl group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₂ -C ₆ alkenyl group, halo C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, halo C ₂ -C ₆ alkynyl group, tri C ₁ -C ₆ alkylsilyl C ₂ -which may be the same or different C ₆ alkynyl group, phenyl C ₂ -C
₆ alkynyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, hydroxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylcarbonyloxy C ₁ -C ₆ alkyl group, C _3- C ₆ cycloalkyl group, halo C ₃ -C ₆ cycloalkyl group, C ₃ -C ₆ cycloalkyl C ₁ -C ₆ alkyl group, halo C ₃ -C ₆ cycloalkyl C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxy group, phenyl C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ alkylthio C _1- C ₆ alkyl group, halo C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkyl sulfinyl C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl sulfinyl C ₁ -C ₆ alkyl group C ₁ -C ₆ alkylsulfonyl C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkylsulfonyl C ₁ -C ₆ alkyl group, mono C ₁ -C ₆ alkylamino group, same or different di-C ₁ -C ₆ alkylamino group, phenylamino group, mono C ₁ -C ₆ alkylamino C ₁ -C ₆ alkyl group, the same or different and may di C ₁ -C ₆ alkylamino C ₁ -C ₆ alkyl group, Phenyl group, which may be the same or different, halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy groups, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkyl Rufiniru group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, the same or di C ₁ may be different -C ₆ alkylamino group or a C ₁ A substituted phenyl group having one or more substituents selected from —C ₆ alkoxycarbonyl groups,

Phenoxy group, which may be the same or different, halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ Alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, one or more substituents selected from mono-C ₁ -C ₆ alkylamino group, the same or different and may di C ₁ -C ₆ alkylamino group or a C ₁ -C ₆ alkoxycarbonyl group A substituted phenoxy group having a group, a heterocyclic group or the same or different, a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ Alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group And a substituted heterocyclic group having one or more substituents selected from a di-C ₁ -C ₆ alkylamino group or a C ₁ -C ₆ alkoxycarbonyl group, which may be the same or different.

Further, two adjacent Ys on the pyrazine ring can be combined to form a condensed ring, which may be the same or different, and are a halogen atom, a cyano group, a nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C _1- C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, the same or different It may also have one or more substituents selected from good di-C ₁ -C ₆ alkylamino groups or C ₁ -C ₆ alkoxycarbonyl groups. m and n represent an integer of 1 to 3. } The substituted pyrazinecarboxylic acid anilide derivative | guide_body represented by these, its salts, the agricultural and horticultural chemical | medical agent which uses this compound as an active ingredient, and its usage method.

｛式中、Ｒ¹は水素原子、C₁-C₆アルキル基、ハロC₁-C₆アルキル基、C₁-C₆アルキルカルボニル基、ハロC₁-C₆アルキルカルボニル基、C₁-C₆アルキルカルボニルC₁-C₆アルキル基、シクロC₃-C₆アルキル基、ハロシクロC₃-C₆アルキル基、シクロC₃-C₆アルキルC₁-C₆アルキル基、ハロシクロC₃-C₆アルキルC₁-C₆アルキル基、C₂-C₆アルケニル基、ハロC₂-C₆アルケニル基、C₂-C₆アルキニル基、ハロC₂-C₆アルキニル基、C₁-C₆アルコキシC₁-C₆アルキル基、ハロC₁-C₆アルコキシC₁-C₆アルキル基、C₁-C₆アルコキシC₁-C₆アルコキシC₁-C₆アルキル基、C₁-C₆アルキルチオC₁-C₆アルキル基、ハロC₁-C₆アルキルチオC₁-C₆アルキル基、C₁-C₆アルキルスルフィニルC₁-C₆アルキル基、ハロC₁-C₆アルキルスルフィニルC₁-C₆アルキル基、C₁-C₆アルキルスルホニルC₁-C₆アルキル基、ハロC₁-C₆アルキルスルホニルC₁-C₆アルキル基、モノC₁-C₆アルキルアミノC₁-C₆アルキル基、同一又は異なっても良いジC₁-C₆アルキルアミノC₁-C₆アルキル基、フェニルC₁-C₆アルコキシC₁-C₆アルキル基、C₁-C₆アルコキシカルボニル基、C₁-C₆アルコキシC₁-C₆アルコキシカルボニル基、ハロC₁-C₆アルコキシカルボニル基、C₁-C₆アルキルチオカルボニル基、モノC₁-C₆アルキルアミノカルボニル基、同一又は異なっても良いジC₁-C₆アルキルアミノカルボニル基、C₁-C₆アルコキシカルボニルC₁-C₆アルキル基、C₁-C₆アルキルスルホニル基、ハロC₁-C₆アルキルスルホニル基、シアノC₁-C₆アルキル基、 Further, the present invention is an intermediate of the general formula (II)

{Wherein R ¹ is a hydrogen atom, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkylcarbonyl group, a halo C ₁ -C ₆ alkylcarbonyl group, C ₁ -C ₆ alkylcarbonyl C ₁ -C ₆ alkyl group, cyclo C ₃ -C ₆ alkyl group, halocyclo C ₃ -C ₆ alkyl group, cyclo C ₃ -C ₆ alkyl C ₁ -C ₆ alkyl group, halocyclo C ₃ -C ₆ Alkyl C ₁ -C ₆ alkyl group, C ₂ -C ₆ alkenyl group, halo C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, halo C ₂ -C ₆ alkynyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkyl sulfinyl C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl sulfinyl C ₁ -C ₆ alkyl group group, C ₁ -C ₆ alkyl Sulfonyl C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkylsulfonyl C ₁ -C ₆ alkyl group, mono-C ₁ -C ₆ alkylamino C ₁ -C ₆ alkyl group, the same or different and may di C ₁ -C ₆ alkylamino C ₁ -C ₆ alkyl group, phenyl C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxycarbonyl group, halo C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkyl thio group, mono C ₁ -C ₆ alkylaminocarbonyl group, the same or different di C ₁ may be -C ₆ alkylaminocarbonyl groups, C ₁ -C ₆ alkoxycarbonyl C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, a cyano C ₁ -C ₆ alkyl group,

Phenyl C ₁ -C ₆ alkyl group, which may be the same or different, halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, Halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ Selected from alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di-C ₁ -C ₆ alkylamino group which may be the same or different or C ₁ -C ₆ alkoxycarbonyl group A substituted phenyl C ₁ -C ₆ alkyl group having one or more substituents on the ring, a phenoxycarbonyl group, which may be the same or different, a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy Group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ One or more substituents selected from a —C ₆ alkylsulfonyl group, a mono C ₁ -C ₆ alkylamino group, a di C ₁ -C ₆ alkylamino group or a C ₁ -C ₆ alkoxycarbonyl group which may be the same or different; Substituted phenoxycarbonyl group, phenylsulfonyl group, which may be the same or different, halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ - C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl , Mono C ₁ -C ₆ alkylamino group, the same or different and may di C ₁ -C ₆ alkylamino group or a C ₁ -C ₆ alkoxy-substituted phenylsulfonyl group having one or more substituents selected from the group , same or different good di C ₁ -C ₆ alkyl phosphono group, the same or different di C ₁ may be -C ₆ Alkylphosphonothioate group, NC ₁ -C ₆ alkyl -NC ₁ -C ₆ alkoxycarbonylamino thio, NC ₁ -C ₆ alkyl -NC ₁ -C ₆ alkoxycarbonyl C ₁ -C ₆ alkylamino thio group, the same or different and may di C ₁ -C ₆ alkylamino thio group or a cycloalkyl C ₃ -C, _{6 represents} an alkylcarbonyl group.

R ² is a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, a cyano group,
Hydroxy group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkoxy C ₁ -C ₃ alkoxy group, halo C ₁ -C ₆ alkoxy C ₁ -C ₃ alkoxy group, C ₁ -C ₆ alkylthio C ₁ -C ₃ alkoxy group, halo C ₁ -C ₆ alkylthio C ₁ -C ₃ alkoxy groups, C ₁ -C ₆ alkylsulfinyl C ₁ -C ₃ alkoxy group, halo C ₁ -C ₆ alkyl Sulfinyl C ₁ -C ₃ alkoxy group, C ₁ -C ₆ alkylsulfonyl C ₁ -C ₃ alkoxy group, halo C ₁ -C ₆ alkylsulfonyl C ₁ -C ₃ alkoxy group, mono C ₁ -C ₆ alkylamino C ₁ -C ₃ alkoxy group, di-C ₁ -C ₆ alkylamino C ₁ -C ₃ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ , which may be the same or different alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, A Amino group, mono C ₁ -C ₆ alkylamino group, the same or different and may di C ₁ -C ₆ alkylamino group, a phenoxy group, which may be identical or different, a halogen atom, a cyano group, a nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio groups, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, the same or different A substituted phenoxy group having one or more substituents selected from a di C ₁ -C ₆ alkylamino group or a C ₁ -C ₆ alkoxycarbonyl group, a phenylthio group, which may be the same or different, a halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ al Group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ - C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di C ₁ -C ₆ alkylamino group which may be the same or different Or a substituted phenylthio group having one or more substituents selected from C ₁ -C ₆ alkoxycarbonyl groups,

Phenylsulfinyl group, which may be identical or different, a halogen atom, a cyano group, a nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo One or more selected from a C ₁ -C ₆ alkylsulfonyl group, a mono C ₁ -C ₆ alkylamino group, a di C ₁ -C ₆ alkylamino group which may be the same or different, or a C ₁ -C ₆ alkoxycarbonyl group Substituted substituted phenylsulfinyl group, phenylsulfonyl group, which may be the same or different, halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ Alkylthio group, a halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, A substituted phenylsulfonyl group having one or more substituents selected from a mono C ₁ -C ₆ alkylamino group, a di C ₁ -C ₆ alkylamino group which may be the same or different, or a C ₁ -C ₆ alkoxycarbonyl group, A phenyl C ₁ -C ₆ alkoxy group, which may be the same or different, a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, Halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ Alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group Substituted on the ring with one or more substituents selected from a mono C ₁ -C ₆ alkylamino group, a di C ₁ -C ₆ alkylamino group which may be the same or different, or a C ₁ -C ₆ alkoxycarbonyl group A phenyl C ₁ -C ₆ alkoxy group;

G is a C ₂ -C ₁₀ alkyl group, a halo C ₂ -C ₁₀ alkyl group, a C ₃ -C ₁₀ alkenyl group, a halo C ₃ -C ₁₀ alkenyl group, a C ₃ -C ₁₀ alkynyl group, a halo C ₃ -C ₁₀ An alkynyl group, a C ₃ -C ₁₀ cycloalkyl group, which may be the same or different and has one or more substituents selected from a halogen atom, a C ₁ -C ₆ alkyl group or a halo C ₁ -C ₆ alkyl group C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, which may be the same or different, and one or more selected from a halogen atom, a C ₁ -C ₆ alkyl group or a halo C ₁ -C ₆ alkyl group A substituted C ₃ -C ₁₀ cycloalkenyl group, a C ₃ -C ₈ cycloalkyl C ₁ -C ₆ alkyl group or a halo C ₃ -C ₈ cycloalkyl C ₁ -C ₆ alkyl group having the following substituents:

｛式中、Ｙ’は同一又は異なっても良く、ハロC₁-C₆アルキル基を示す。Ｒ¹’は水素原子又はC₁-C₆アルキル基を示す。ｍは１〜３の整数を示す。｝で表される置換ピラジンカルボン酸誘導体及びその塩類にも関する。 X may be the same or different and each represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group or a halo C ₁ -C ₆ alkyl group. n shows the integer of 1-3. } Substituted aniline derivatives and salts thereof, and
General formula (III ')

{Wherein Y's may be the same or different and each represents a halo C ₁ -C ₆ alkyl group. R ¹ ′ represents a hydrogen atom or a C ₁ -C ₆ alkyl group. m shows the integer of 1-3. }, And substituted salts thereof.

  ADVANTAGE OF THE INVENTION According to this invention, the agricultural and horticultural chemical | medical agent which has the performance outstanding compared with the prior art, especially an insecticide and an acaricide can be provided.

In the definitions of the general formula (I) of the substituted pyrazinecarboxylic acid anilide derivative of the present invention, the general formula (II) of the substituted aniline derivative and the general formula (III ′) of the substituted pyrazinecarboxylic acid derivative, “halo” in each substituent, “C ₁ -C ₆ alkyl”, “C ₁ -C ₆ alkoxy”, “C ₂ -C ₆ alkenyl”, “C ₂ -C ₆ alkynyl”, “heterocycle” and the like have the following meanings.
“Halo” or “halogen atom” refers to a chlorine atom, a bromine atom, an iodine atom or a fluorine atom. “C ₁ -C ₆ alkyl” refers to linear or branched alkyl having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i- Examples include butyl, s-butyl, t-butyl, n-pentyl, n-hexyl and the like. “C ₃ -C ₁₀ cycloalkyl” indicates cyclic alkyl having 3 to 10 carbon atoms, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, cyclodecyl and the like. “C ₁ -C ₆ alkoxy” means an alkoxy whose alkyl moiety is the above “C ₁ -C ₆ alkyl”, for example, methoxy, ethoxy, propoxy, butoxy, isobutoxy, t-butoxy, pentyloxy, hexyl Examples include oxy. “C ₂ -C ₆ alkenyl” refers to a straight or branched alkenyl having 2 to 6 carbon atoms having at least one double bond, such as vinyl, 1-propenyl, allyl, 1 -Butenyl, 2-butenyl, 3-butenyl, 2-pentenyl, 2,4-pentadienyl, 3-hexenyl and the like can be mentioned. “C ₂ -C ₆ alkynyl” refers to linear or branched alkynyl having at least one triple bond and having 2 to 6 carbon atoms, such as ethynyl, 2-propynyl, 1-butynyl, Examples include 2-butynyl, 3-butynyl, 2-pentynyl, 3-hexynyl and the like. The numbers such as “C ₂ -C ₆ ” and “C ₃ -C ₁₀ ” indicate the range of the number of carbon atoms such as 2 to 6, 3 to 10 carbon atoms. Further, the above definition can be given for a group to which the above substituent is linked. For example, in the case of “halo C ₁ -C ₆ alkyl”, the group is directly substituted with one or more halogen atoms which may be the same or different. A chain or branched alkyl group having 1 to 6 carbon atoms is shown, and examples thereof include difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, perfluorohexyl and the like.

“Heterocyclic group” refers to a 5- or 6-membered heterocyclic group having one or more heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, such as a pyridyl group, a pyridine-N-oxide group, and a pyrimidinyl group. Group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, tetrahydrothiopyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, imidazolyl group, triazolyl group And a pyrazolyl group. Examples of the “fused ring” include naphthalene, tetrahydronaphthalene, indene, indane, quinoline, quinazoline, indole, indoline, chroman, isochroman, benzodioxane, benzodioxole, benzofuran, dihydrobenzofuran, benzothiophene, dihydrobenzothiophene, Examples include benzoxazole, benzothiazole, benzimidazole, and indazole.

Of the general formula (I) of the substituted pyrazinecarboxylic acid anilide derivative of the present invention, the general formula (II) of the substituted aniline derivative, and the general formula (III ′) of the substituted pyrazinecarboxylic acid derivative, R ¹ is preferably a hydrogen atom, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylcarbonyl group, halo C ₁ -C ₆ alkylcarbonyl group, C ₁ -C ₆ alkoxycarbonyl group, halo C ₁ -C ₆ Alkoxycarbonyl group, C ₁ -C ₆ alkylcarbonyl C ₁ -C ₆ alkyl group, C ₂ -C ₆ alkenyl group, halo C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, halo C ₂ -C ₆ Alkynyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group or C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group a group, more preferably a hydrogen atom, C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ A Le kill carbonyl group or a C ₁ -C ₆ alkoxycarbonyl.

R ² is preferably a hydrogen atom, halogen atom, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, hydroxy group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ —C ₆ alkoxy C ₁ -C ₃ alkoxy group or halo C ₁ -C ₆ alkoxy C ₁ -C ₃ alkoxy group, more preferably a hydrogen atom, halogen atom or C ₁ -C ₆ alkoxy group.
G is preferably a C ₂ -C ₁₀ alkyl group, a halo C ₂ -C ₁₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group or a C ₃ -C ₈ cycloalkyl C ₁ -C ₆ alkyl group, particularly preferably C ₂ -C ₁₀ alkyl group or C ₃ -C ₈ cycloalkyl C ₁ -C ₆ alkyl group.
X is particularly preferably a hydrogen atom. Y is preferably a halogen atom, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group or halo C ₁ -C ₆ alkoxy group, particularly preferably C ₁ -C _{A 6} alkyl group or a halo C ₁ -C ₆ alkyl group. m is preferably 1 or 2, particularly preferably 1. Z is preferably an oxygen atom.

  Examples of the salt of the substituted pyrazinecarboxylic acid anilide derivative represented by the general formula (I) or the intermediate of the substituted pyrazinecarboxylic acid derivative represented by the general formula (III ′) of the present invention include alkali metals (lithium, sodium Salt, alkaline earth metal (calcium, magnesium, etc.) salt, ammonium salt, organic amine (methylamine, triethylamine, diethanolamine, piperidine, pyridine, etc.) salt or acid addition salt, etc. Examples of the addition salt include carboxylates such as acetate, propionate, oxalate, trifluoroacetate, benzoate, methanesulfonate, trifluoromethanesulfonate, p-toluenesulfonate, and the like. Inorganic acid salts such as sulfonates, hydrochlorides, sulfates, nitrates, and carbonates.

The salt of the substituted aniline derivative represented by the general formula (II) is preferably an acid addition salt, for example, a carboxylate such as acetate, propionate, oxalate, trifluoroacetate, benzoate, etc. , Sulfonates such as methanesulfonate, trifluoromethanesulfonate, and p-toluenesulfonate, and inorganic acid salts such as hydrochloride, sulfate, nitrate, and carbonate.
The substituted pyrazinecarboxylic acid anilide derivative represented by the general formula (I) of the present invention or the substituted aniline derivative represented by the general formula (II), which is an intermediate thereof, contains one or a plurality of non-substituted aniline derivatives in the structural formula. It may contain a chiral center, and there may be two or more optical isomers and diastereomers, and the present invention includes all of the optical isomers and a mixture containing them in an arbitrary ratio. It is. In addition, the substituted pyrazinecarboxylic acid anilide derivative represented by the general formula (I) of the present invention may have two geometric isomers derived from a carbon-carbon double bond in the structural formula, The present invention encompasses all the geometric isomers and mixtures containing them in any proportion.

  The substituted pyrazinecarboxylic acid anilide derivative represented by the general formula (I) of the present invention, the substituted aniline derivative represented by the general formula (II) as an intermediate thereof, or the substitution represented by the general formula (III ′) below. Although the typical manufacturing method of a pyrazine carboxylic acid derivative is shown, this invention is not limited to these.

（式中、Ｒ¹、Ｒ²、Ｇ、Ｘ、Ｙ、ｍ及びｎは前記に同じくし、Ｒ³は水素原子、C₁-C₆アルキル基、ハロC₁-C₆アルキル基、フェニル基、置換フェニル基又はフェニルC₁-C₄アルキル基を示し、Ｗは−Ｏ−、−Ｓ−又は−Ｎ（Ｒ⁴）−（式中、Ｒ⁴は水素原子、C₁-C₆アルキル基、ハロC₁-C₆アルキル基、フェニル基、置換フェニル基又はフェニルC₁-C₄アルキル基を示す。）を示し、Ｑはハロゲン原子又はC₁-C₆アルコキシ基を示す。） Manufacturing method 1

(Wherein R ¹ , R ² , G, X, Y, m and n are the same as above, R ³ is a hydrogen atom, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, a phenyl group. Represents a substituted phenyl group or a phenyl C ₁ -C ₄ alkyl group, W is —O—, —S— or —N (R ⁴ ) — (wherein R ⁴ is a hydrogen atom, C ₁ -C ₆ alkyl group) A halo C ₁ -C ₆ alkyl group, a phenyl group, a substituted phenyl group or a phenyl C ₁ -C ₄ alkyl group), and Q represents a halogen atom or a C ₁ -C ₆ alkoxy group.

Among the substituted pyrazinecarboxylic acid anilide derivatives represented by the general formula (I), the substituted pyrazinecarboxylic acid anilide derivatives (I-2) in which Z is represented by O are represented by the general formulas (II-1) to (II). -3) by reacting the aniline derivative represented by the general formula (III) with the pyrazinecarboxylic acid halide or pyrazinecarboxylic acid ester in the presence or absence of a base in an inert solvent, or An aniline derivative represented by general formula (II-1) to general formula (II-3) and a pyrazinecarboxylic acid represented by general formula (IV) in the presence of a condensing agent, in the presence or absence of a base. It can be produced by reacting in an inert solvent, but any ordinary method for producing amides may be used.
The aniline derivative represented by the general formula (II-2) can be produced by reducing the aniline derivative represented by the general formula (II-1) in an inert solvent in the presence of a reducing agent.
The aniline derivative represented by the general formula (II-3) is represented by the general formula (V) in an inert solvent in the presence or absence of a base. Can be produced by reacting with an alcohol derivative, thiol derivative or amine derivative.

General formula (II-1) → General formula (II-2)
Examples of the reducing agent that can be used in this reaction include lithium aluminum hydride, lithium borohydride, sodium borohydride, diisobutylaluminum hydride, metal hydride such as sodium bis (2-methoxyethoxy) aluminum hydride, and lithium metal. A metal or a metal salt can be exemplified, and the amount used can be appropriately selected from the range of equivalent to excess amount with respect to the aniline derivative represented by the general formula (II-1).
The inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction. For example, aromatic hydrocarbons such as benzene, toluene and xylene, halogens such as methylene chloride, chloroform and carbon tetrachloride. Inert solvents such as halohydrocarbons, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, and chain or cyclic ethers such as diethyl ether, dioxane and tetrahydrofuran (THF) can be exemplified. An inert solvent can be used individually or in mixture of 2 or more types.
The reaction temperature can be from room temperature to the boiling point of the inert solvent to be used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 50 hours.
After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary. Moreover, it is also possible to use for the next reaction process, without isolating a target object from a reaction system.

General formula (II-1) → General formula (II-3)
Bases that can be used in this reaction include metal hydrides such as lithium hydride, sodium hydride and potassium hydride, metal alcoholates such as sodium methoxide, sodium ethoxide and potassium t-butoxide, n-butyllithium, s- Examples thereof include alkyl metals such as butyl lithium and t-butyl lithium, and the amount used is appropriately selected from the range of equivalent to excess amount with respect to the aniline derivative represented by the general formula (II-1). Use it.
The inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction. For example, aromatic hydrocarbons such as benzene, toluene and xylene, alcohols such as methanol and ethanol, diethyl ether, Inert solvents such as linear or cyclic ethers such as 1,2-dimethoxyethane, dioxane and tetrahydrofuran can be exemplified, and these inert solvents can be used alone or in admixture of two or more. .
The reaction temperature can be carried out in the range of -70 ° C. to the boiling point of the inert solvent to be used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 50 hours.
After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary. Moreover, it is also possible to use for the next reaction process, without isolating a target object from a reaction system.

General formula (II-1), general formula (II-2) or general formula (II-3) → general formula (I-2)
Examples of the condensing agent used in this reaction include diethyl cyanophosphate (DEPC), carbonyldiimidazole (CDI), 1,3-dicyclohexylcarbodiimide (DCC), chlorocarbonates, 2-chloro-1-methylpyridinium iodide. Etc. can be illustrated.
Examples of the base used in this reaction include inorganic bases and organic bases. Examples of inorganic bases include hydroxides of alkali metal atoms such as sodium hydroxide and potassium hydroxide, sodium hydride and potassium hydride. Alkali metal hydrides, alkali metal salts of alcohols such as sodium ethoxide and potassium t-butoxide, carbonates such as sodium carbonate, potassium carbonate and sodium bicarbonate, and organic bases include, for example, triethylamine, pyridine, DBU, etc. The amount used may be selected from the range of equimolar to excess molar relative to the pyrazinecarboxylic acid derivative represented by the general formula (III) or (IV).

The inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction. For example, aromatic hydrocarbons such as benzene, toluene and xylene, halogens such as methylene chloride, chloroform and carbon tetrachloride. Hydrocarbons, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, chain or cyclic ethers such as diethyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, amides such as dimethylformamide and dimethylacetamide , Dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, and inert solvents such as acetone and methyl ethyl ketone. These inert solvents may be used alone or in admixture of two or more. it can.
Since this reaction is an equimolar reaction, each reactant may be used in an equimolar amount, but any of the reactants can be used in excess, and the reaction temperature ranges from room temperature to the boiling point of the inert solvent used. Although the reaction time is not constant depending on the reaction scale and reaction temperature, it may be carried out in the range of several minutes to 48 hours.
After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
The aniline derivative represented by the general formula (II-1), which is a raw material compound for this reaction, can be produced according to the production method disclosed in JP-A-11-302233 or 2001-1222836. it can.

In addition, pyrazinecarboxylic acid derivatives represented by the general formula (III), (III ′), or (IV) are known literatures (for example, Journal of Organic Chemistry, Vol. 67 , 556-565 (2002), Journal of American Chemical). Society Vol. 70, 3911 (1948 ), Chemical & Pharmaceutical Bulletin, 20 (10) 2204~2208 (1970), Journal of Heterocyclic Chemistry, Vol. 34, 27 (1997), Synthesis 923-924 (1990), WO2001070708, Tetrahedron Letters , Vol 32 , No 52, 7689-7690 (1991), J our of American
Chemical Society Vol. 68 , 400 (1946) and the like. ) Can be produced according to the method described.

（式中、Ｒ¹ 、Ｒ² 、Ｇ、Ｘ、Ｙ、ｍ及びｎは前記に同じ。）
一般式（Ｉ）で表される置換ピラジンカルボン酸アニリド誘導体のうち、ＺがＳで表される置換ピラジンカルボン酸アニリド誘導体（I−３）は、（I−２）で表されるアニリン誘導体を公知の方法（Ｔｅｔｒａｈｅｄｒｏｎ Ｌｅｔｔ．，２１（４２），４０６１（１９８０））に準じてローソン試薬と反応させることにより製造することができる。 Manufacturing method 2

(In the formula, R ¹ , R ² , G, X, Y, m and n are the same as above.)
Among the substituted pyrazinecarboxylic acid anilide derivatives represented by the general formula (I), the substituted pyrazinecarboxylic acid anilide derivative (I-3) in which Z is represented by S is an aniline derivative represented by (I-2). It can be produced by reacting with a Lawson reagent according to a known method (Tetrahedron Lett., 21 (42), 4061 (1980)).

（式中、Ｒ¹ 、Ｒ² 、Ｇ、Ｘ、Ｙ、Ｑ、ｍ及びｎは前記に同じ。）
一般式（Ｉ）で表される置換ピラジンカルボン酸アニリド誘導体のうち、Ｒ¹が水素原子以外の置換ピラジンカルボン酸アニリド誘導体（I−２）は、一般式（I−２a）で表されるアミド誘導体と一般式（VI）で表されるハライド誘導体又はエステル誘導体を
塩基の存在下又は不存在下に、不活性溶媒中で反応させることにより製造することができる。 Manufacturing method 3

(Wherein R ¹ , R ² , G, X, Y, Q, m and n are the same as above)
Of the substituted pyrazinecarboxylic acid anilide derivatives represented by general formula (I), substituted pyrazinecarboxylic acid anilide derivatives (I-2) other than those in which R ¹ is a hydrogen atom are amides represented by general formula (I-2a) It can be produced by reacting a derivative with a halide derivative or ester derivative represented by the general formula (VI) in the presence or absence of a base in an inert solvent.

Bases that can be used in this reaction include metal hydrides such as lithium hydride, sodium hydride and potassium hydride, metal alcoholates such as sodium methoxide, sodium ethoxide and potassium t-butoxide, n-butyllithium, s- Examples thereof include alkyl metals such as butyl lithium and t-butyl lithium, and the amount used thereof is appropriately selected from the range of equivalent to excess amount with respect to the amide derivative represented by the general formula (I-2a). Use it.
The inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction. For example, aromatic hydrocarbons such as benzene, toluene and xylene, alcohols such as methanol and ethanol, diethyl ether, Inert solvents such as linear or cyclic ethers such as 1,2-dimethoxyethane, dioxane and tetrahydrofuran can be exemplified, and these inert solvents can be used alone or in admixture of two or more. .
The reaction temperature can be carried out in the range of -70 ° C. to the boiling point of the inert solvent to be used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 50 hours.
After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary. Moreover, it is also possible to use for the next reaction process, without isolating a target object from a reaction system.

Representative compounds of the substituted pyrazinecarboxylic acid anilide derivatives represented by the general formula (I) are shown in Table 1, typical compounds of the substituted aniline derivatives represented by the general formula (II) are shown in Table 2, and The substituted pyrazinecarboxylic acid derivatives represented by the formula (III ′) are exemplified in Table 3, but the present invention is not limited thereto. Further, the melting point (° C.) or refractive index [n _D (° C.)] is described in the “Physical Properties” column in Table ¹ , and the ¹ HNMR data of the compound described as amorphous is shown in Table 4. . In the table, “n-” is normal, “i-” is iso, “t-” is tertiary, “c-” is cyclo, “Me” is methyl group, “Et” is “Pr” represents a propyl group, “Bu” represents a butyl group, “Ph” represents a phenyl group, and “Ac” represents an acetyl group.

Agricultural and horticultural agents containing a substituted pyrazinecarboxylic acid anilide derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient, in particular, agricultural and horticultural insecticides, or acaricides are rice, fruit trees, vegetables, It is suitable for various agricultural and forestry, horticulture, stored grain pests, hygienic pests, nematodes, and other pests that harm crops and flowers. For example, Adoxophyes orana fasciata, Adoxophyes sp. ), Apple crocodile (Grapholita inopinata), pear beetle (Grapholita molesta), bean tiger moth (Leguminivora glycinivorella), sculpture (Olethreutes mori), chanohosoga (Caloptilia thevivora), apple phosoga (Caloptilia zachrysaga)
ringoniella, Spulerrina astaurota, Piers rapae crucivora, Giant tobacco (Heliothis sp.), Codylinga (Laspey resia pomonella), Plutella xylostella, Argyresthia conjuinapon, Argyresthia conjuina ), Green leaf moth (Chilo suppressalis), yellow leaf moth (Cnaphalocrocis medinalis), yellowtail moth (Ephestia elutella), white corn borer (Glyphodes pyloalis), sun corn borer (Scirpophaga incertulas), parsara gulete (es) ), Lepidoptera such as Spodoptera litura, Spodoptera exigua,

Leafhopper leafhopper (Macrosteles fascifrons), Leafhopper leafhopper (Nephotettix cincticeps), Leafhopper (Nilaparvata lugens), White-throated leafhopper (Sogatella furcifera), Citrus leaffly (Diaphorina citri), Grape leafworm (Aleurolobus tayona) ), Aphid lipase (Lipaphis erysimi), Alaska aphid (Myzus persicae), horned beetle (Ceroplastes ceriferus), Pulvinaria aurantii, Pseudaonidia duplex, Niomaru asparagus nic Hemiptera pests such as scale insects (Unaspis yanonensis), Japanese beetle (Anomala rufocuprea), Japanese beetle (Popilla japonica), tobacco beetle (Lasioderma serricorne), Japanese beetle (Lyctus b) runneus), Epilachna vigintiotopunctata, Azuki weevil (Callosobruch)
us chinensis), weevil (Listroderes costirostris), weevil (Sitophilus zeamais), cotton weevil (Anthonomus grandis grandis), rice weevil (Lissorhoptrus oryzophilus), urihamushi (Aulacophora femoralis), rice reort yz Coleopterous pests such as bark beetle (Tomicus piniperda), Colorado potato beetle (Leptinotarsa decemlineata), Mexican beetle (Epilachna varivestis), corn root worms (Diabrotica sp.),

Drosophila (Dacus (Zeugodacus) cucurbitae), citrus fruit fly (Dacus (Bactrocera) dorsalis), rice leaf fly (Agromyza oryzae), onion fly (Delia antiqua), fly fly (Dalia platura), soybean flies (Asphondy) sp. Pests, Pratylenchus coffeae, potato cyst nematodes (Glabodera rostchiensis), root-knot nematodes (Meloidogyne sp.), Citrus nematodes (Tylenchulus semipenetrans), flounder (Aphelenchus phecho) The pestid insect of the order of the red-spotted nematode (Panonychus citri), apple tick (Panonychus ulmi), black tick mite (Tetranychus cinnabarinus), kanzawai tick (Tetranychus kanzawai Kishida), nite spider mite (Tetranychus urticae Koch) tick (Tetranychus urticae Koch) It has a strong insecticidal effect against pests such as Aculops pelekassi, Calacarus carinatus, and Epitrimerus pyri.

  The substituted pyrazinecarboxylic acid anilide derivative represented by the general formula (I) of the present invention or a salt thereof is preferably used as an agricultural or horticultural insecticide or an acaricide, but for forest and wood pests, livestock pests, hygiene Exhibits excellent control effects against various pests such as insect pests, and can be used as a pest control agent in a wide range of fields. Examples of these pests include houseflies such as Yamato Abu and house flies such as house flies. Family, euphoridae such as flies, bullidae such as cattle flies, flea flies such as fleaflies, flea flies such as mosquito flies, mosquitoes, crested mosquitoes, cicadas such as yamatoyabuka, flea departments such as cat fleas, dog fleas, fleas, etc. , Spodoptera, such as Japanese weevil, Colossophoridae, such as weevil, hornet, such as killer hornet, chaban German cockroach family such as Kibuli, American cockroach, blattidae such as Yamato cockroaches, crab louse family such as crab louse, termites, termites family such as Formosan subterranean termite, Ixodidae such as Schulze ticks, can be mentioned Oosashidani department such as house dust mite.

Agricultural and horticultural agents, in particular, agricultural and horticultural insecticides or acaricides, containing the substituted pyrazinecarboxylic acid anilide derivatives represented by the general formula (I) of the present invention or salts thereof as paddy field crops, field crops, fruit trees Since it has a remarkable control effect against the above-mentioned pests that damage vegetables, other crops and flowers, etc., when the occurrence of the pests is confirmed, or when the occurrence is confirmed The desired effect of the agricultural and horticultural insecticide of the present invention can be obtained by treating the paddy field, fields, fruit trees, vegetables, other crops, seeds such as flower buds, paddy water, foliage or soil.
Although the plant which can use the agricultural and horticultural chemical | medical agent of this invention is not specifically limited, For example, the plant shown below is mentioned.

Cereals (for example, rice, barley, wheat, rye, oats, corn, coconut, etc.), beans (soybeans, red beans, broad beans, peas, peanuts, etc.), fruit trees and fruits (apples, citrus fruits, pears, grapes, Peaches, plums, cherry peaches, walnuts, almonds, bananas, strawberries, etc.), vegetables (cabbage, tomatoes, spinach, broccoli, lettuce, onions, leeks, peppers, etc.), root vegetables (carrots, potatoes, sweet potatoes, radishes, lotus roots, Turnips, etc.), processing crops (cotton, hemp, mulberry, mitsumata, rapeseed, beet, hops, sugar cane, sugar beet, olives, rubber, coffee, tobacco, tea, etc.), potatoes (pumpkin, cucumber, watermelon, melon, etc.) ), Grass (orchardgrass, sorghum, timothy, clover, alfalfa, etc.), turf (Korean turf, bentgrass, etc.), crops for fragrances, etc. Lavender, rosemary, thyme, parsley, pepper, ginger, etc.), it can be used flowering plants (chrysanthemums, roses, plants of orchids, etc.) and the like.
In recent years, genetically modified crops (herbicide-tolerant crops, pest-resistant crops incorporating insecticidal protein production genes, disease-resistant crops incorporating resistance-inducing substance production genes against disease, improved taste crops, preserved crops, yield Improved crops, etc.), insect pheromones (communication agents such as toads, moths, etc.), natural enemy insects, etc. have advanced IPM (Integrated Pest Management) technology. Can be used in combination with technology or systematized.

The agricultural and horticultural chemicals of the present invention are generally used in a form convenient for use according to a conventional method for agricultural chemical preparations.
That is, the substituted pyrazinecarboxylic acid anilide derivatives represented by the general formula (I) or salts thereof are dissolved and separated by blending them in a suitable inert carrier or, if necessary, with an auxiliary agent in a suitable ratio. , Suspended, mixed, impregnated, adsorbed or adhered, and formulated into appropriate dosage forms such as suspensions, emulsions, solutions, wettable powders, wettable granules, granules, powders, tablets, packs, etc. Use it.

  The inert carrier that can be used in the present invention may be either solid or liquid. Examples of materials that can be used as a solid carrier include soybean flour, cereal flour, wood flour, bark flour, saw flour, and tobacco stem flour. , Walnut shell powder, bran, fiber powder, residue after extraction of plant extract, synthetic polymer such as ground synthetic resin, clays (eg kaolin, bentonite, acid clay), talc (eg talc, pyrophyllite, etc.), Silicas {for example, diatomaceous earth, silica sand, mica, white carbon (some synthetic high-dispersion silicic acid called water-containing fine silicon and water-containing silicic acid, and some products contain calcium silicate as a main component)}, activated carbon, sulfur powder, pumice, Firing diatomaceous earth, brick ground, fly ash, sand, calcium carbonate, calcium phosphate and other inorganic mineral powders, polyethylene, polypropylene, polychlorinated Plastic carriers such as vinylidene, ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, fertilizer salts depreciation etc., can be exemplified compost or the like, which are used alone or in the form of a mixture of two or more.

  The material that can be used as a liquid carrier is selected from those having solvent ability itself and those capable of dispersing the active ingredient compound with the aid of an auxiliary agent without having solvent ability. The following carriers can be exemplified, but these are used alone or in the form of a mixture of two or more thereof, for example, water, alcohols (for example, methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.), ketones (for example, acetone) , Methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.), ethers (eg, ethyl ether, dioxane, cellosolve, dipropyl ether, tetrahydrofuran, etc.), aliphatic hydrocarbons (eg, kerosene, mineral oil, etc.), aromatic hydrocarbons (E.g. benzene, true Xylene, solvent naphtha, alkylnaphthalene, etc.), halogenated hydrocarbons (eg, dichloroethane, chloroform, carbon tetrachloride, chlorinated benzene, etc.), esters (eg, ethyl acetate, diisopropylpropyl phthalate, dibutyl phthalate, dioctyl phthalate) And amides (for example, dimethylformamide, diethylformamide, dimethylacetamide, etc.), nitriles (for example, acetonitrile, etc.), dimethylsulfoxides, and the like.

As other adjuvants, typical adjuvants exemplified below can be mentioned, and these adjuvants are used depending on the purpose, and used alone, in some cases, two or more kinds of adjuvants are used together. In some cases it is possible to use no adjuvants at all.
Surfactants are used for the purpose of emulsifying, dispersing, solubilizing and / or wetting of the active ingredient compound, such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene higher fatty acid ester, polyoxyethylene. Examples of surfactants such as resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylaryl sulfonate, naphthalene sulfonate condensate, lignin sulfonate, higher alcohol sulfate Can do.
In addition, for the purpose of stabilizing the dispersion of the active ingredient compound, adhesion and / or binding, the following auxiliary agents can be used, for example, casein, gelatin, starch, methylcellulose, carboxymethylcellulose, gum arabic, polyvinyl Adjuvants such as alcohol, pine oil, coconut oil, bentonite and lignin sulfonate can also be used.

In order to improve the fluidity of solid products, the following adjuvants may be used, and for example, adjuvants such as waxes, stearates and alkyl phosphates may be used. As a peptizer for the suspension product, for example, auxiliary agents such as naphthalenesulfonic acid condensate and condensed phosphate can be used.
As the antifoaming agent, for example, an auxiliary agent such as silicone oil can be used.
As a preservative, 1,2-benzisothiazolin-3-one, parachlorometaxylenol, butyl paraoxybenzoate, and the like can also be added.
Furthermore, functional spreading agents, activity enhancers such as metabolic degradation inhibitors such as piperonyl butoxide, antifreezing agents such as propylene glycol, antioxidants such as BHT, UV absorbers and other additives as necessary Agents can also be added.

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 in 100 parts by weight of the agricultural and horticultural insecticide. When it is used as an agent, 0.01 to 50% by weight is appropriate, and when it is used as an emulsion or wettable powder, 0.01 to 50% by weight is also appropriate.
The agricultural or horticultural agent of the present invention is used for controlling various pests as it is, or is appropriately diluted with water or the like, or in a suspended form in an amount effective for controlling pests. May be used by applying it to an unfavorable place.
The amount of the agricultural and horticultural agent used in the present invention varies depending on various factors such as purpose, target pests, crop growth status, pest occurrence tendency, weather, environmental conditions, dosage form, application method, application location, application time, etc. However, the active ingredient compound may be appropriately selected according to the purpose from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg per 10 are.

The agricultural and horticultural chemicals of the present invention are further pests to be controlled, other agricultural and horticultural insecticides, acaricides, nematicides, fungicides, for the purpose of expanding the appropriate period of control or for reducing the dose. It can also be used by mixing with biological pesticides, etc., and can also be used by mixing with herbicides, plant growth regulators, fertilizers, etc., depending on the situation of use.
Other agricultural and horticultural insecticides, acaricides, nematicides used for such purposes include, for example, etion, trichlorfone, methamidophos, acephate, dichlorvos, mevinphos, monocrotophos, malathion, dimethoate, formothion, mecarbam, bamidthione, thiomethone. , Disulfotone, oxydeprophos, nared, methyl parathion, fenitrothion, cyanophos, propaphos, fenthion, prothiophos, profenofos, isofenphos, temefos, phentoate, dimethylvinphos, chlorfevinphos, tetrachlorvinphos, foxime, isoxathion, pyracrophos, methidathion , Chloropyrifos, chlorpyrifos methyl, pyridafenthione, diazinon, pyrimifosmethyl, hosalon, phosmet, geo Sabenzohosu, quinalphos, terbufos, ethoprophos, cadusafos, Mesurufenhosu, DPS (NK-0795),

Phosphocarb, phenamiphos, isoamidophos, isothiafos, isothiafos, enaprofos, fenthion, phosthiethane, diclofenthion, thionadine, sulprophos, fencerfothion, diamidaphos, pyrethrin, allethrin, plaretrin, resmethrin, permethrin, bifluthrin, profenthrin, profenthrin, profenthrin, profenthrin Cypermethrin, cyhalothrin, lambda cyhalothrin, deltamethrin, acrinatrin, fenvalerate, esfenvalerate, cycloprotolin, etofenprox, halfenprox, silafluophene, flucitrinate, fulvalinate, mesomil, oxamyl, thiodicarb, aldicarb, Alanicarb, Cartap, Metorcarb, Kishi Carb, propoxyl, phenoxycarb, fenobucarb, etiofencarb, phenothiocarb, bifenazate, BPMC, carbaryl, pirimicurve, carbofuran, carbosulfan, furthiocarb, benfuracarb, aldoxycarb, diafenthiuron, diflubenzuron, teflubenzuron, hexaflumurone Lufenuron, flufenoxuron, chlorfluazuron, fenbutane oxide, tricyclohexyltin hydroxide, sodium oleate, potassium oleate, methoprene, hydroprene, binaacryl, amitraz, dichor, kelsen, chlorbenzilate, phenisobromolate, Tetradiphone, bensultap, benzomate, tebufenozide, methoxyphenozide, pyridari ,

Chromafenozide, propargite, acequinosyl, endosulfan, diophenolan, chlorfenapyr, fenpyroximate, tolfenpyrad, fipronil, tebufenpyrad, triazamate, etoxazole, hexithazox, nicotine sulfate, nitenpyram, acetamiprid, thiaclopridum, thiaclopridum, thiaclopridom Methylnon, pyrimidifene, pyridaben, cyromazine, TPIC (tripropyl isocyanurate), pymetrozine, clofentezin, buprofezin, thiocyclam, phenazaquin, quinomethionate, indoxacarb, polynactin complex, milbemectin, abamectin, emamectin benzoate , Spinosad, BT (Bacillus thuringiensis), azadirachtin, rotenone, hydroxypropyl starch, levamisole hydrochloride, metam sodium, morantel tartrate, dazomet, trichlamide, bastoria, monacrosporium fimatopagum, etc. Mite and nematicide can be exemplified,

As agricultural and horticultural fungicides used for the same purpose, for example, sulfur, lime sulfur combination, basic copper sulfate, iprobenphos, edifenphos, tolcrofos methyl, thiram, polycarbamate, gnebu, manzeb, mancozeb, propineb, Thiophanate, thiophanate methyl, benomyl, iminotadine acetate, iminotazine albecylate, mepronil, flutolanil, pencyclon, furamethopyl, tifluzamide, metalaxyl, oxadoxyl, carpropamide, diclofluanide, fursulfamide, chlorothalonil, clexoxime methyl, phenoxolyl, methoxanil Fluorimide, Procymidone, Vinclozoline, Iprodione, Triazimephone, Viteltanol, Triflumizole, Ipconazo , Fluconazole, propiconazole, diphenoconazole, microbutanyl, tetraconazole, hexaconazole, tebuconazole, thiazinyl, imibenconazole, prochloraz, pefrazoate, cyproconazole, isoprothiolane, phenalimol, pyrimethanil, mepanipyrim, pyrifenox, fluazinam, fluazinam Agricultural and horticultural fungicides such as dichromedin, azoxystrobin, thiadiazine, captan, probenazole, acibenzofural S methyl, fusaride, tricyclazole, pyroxylone, quinomethionate, oxolinic acid, dithianon, kasugamycin, validamycin, polyoxin, blasticidin, streptomycin Can be illustrated,

Similarly, herbicides include, for example, glyphosate, sulfosate, glufosinate, bialaphos, butamifos, esprocarb, prosulfocarb, beniocarb, pilibutycarb, ashram, linuron, dimron, isouron, bensulfuron methyl, cyclosulfamuron, sinosulfuron, pyrazosulfuron Ethyl, azimusulfuron, imazosulfuron, tenylchlor, alachlor, pretilachlor, clomeprop, etobenzanide, mefenacet, pendimethalin, bifenox, acifluophene, lactofen, cihalohop butyl, ioxynyl, bromobutide, aroxidim, cetoxidim, napropamide pyramide , Benzophenap, pyraflufenethyl, imazapyr, Rufentorazon can cafenstrole, Bentokisazon, oxadiazon, paraquat, diquat, pyriminobac, simazine, atrazine, dimethametryn, triaziflam, benfuresate, fluthiacet-methyl, quizalofop-ethyl, bentazone, it is exemplified herbicides such as calcium peroxide.

  Examples of biological pesticides include nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), insect poxvirus (Entomopox virus, EPV). ) Virus preparations, Monocrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, Pasturia penetrans, etc. As a microbial pesticide, Trichoderma lignorum, Agrobacterium radiobactor, non-pathogenic Erwinia carotovora, Bacillus subtilis, etc. Used That microbial pesticide, by using in such a mixed biopesticide utilized as herbicides, such as Xanthomonas campestris (Xanthomonas campestris), the same effect can be expected.

  Furthermore, examples of biological pesticides include Encarsia formosa; Aphidius colemani; Aphidoletes aphidimyza; ), Natural enemy organisms such as Amblyseius cucumeris, Orius sauteri, microbial pesticides such as Beauveria brongniartii, (Z) -10-tetradecenyl acetate, (E, Z) -4,10-tetradecadinyl acetate, (Z) -8-dodecenyl acetate, (Z) -11-tetradecenyl acetate, (Z) -13-icosen-10-one, (Z) -8- Dodecenyl-acetate, (Z) -11-tetradecenyl-aceta DOO, (Z) -13-icosene-10-one, can be used in combination with pheromone such as 14-methyl-1-octadecene.

The substituted pyrazinecarboxylic acid anilide derivative represented by the general formula (I) of the present invention or the substituted aniline derivative represented by the general formula (II) which is an intermediate thereof will be described below with reference to examples. The invention is not limited to these examples.
Example 1 Preparation of 3-isobutyl-4- [1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl] aniline (Compound No. 2-9) 3-isobutylaniline (14.9 g, 0.1 mol) is diluted with 300 ml of a mixed solvent of tertiary butyl methyl ether-water (1: 1), heptafluoroisopropyl iodide (29.6 g, 0.1 mol), tetrabutylammonium hydrogen sulfate (3.4 g, 0). 0.01 mol), sodium hydrogen carbonate (8.4 g, 0.1 mol) and sodium dithionite (17 g, 0.1 mol) were sequentially added, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with hexane, washed twice with 3N hydrochloric acid, and washed with aqueous sodium hydrogen carbonate and saturated brine. After drying over magnesium sulfate and concentrating under reduced pressure, the residue was separated and purified by silica gel chromatography (hexane: ethyl acetate 6: 1) to obtain 14.9 g of the desired product.
Yield: 47%
Physical properties: ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm)]
7.23 (d, 1H), 6.54 (dt, 1H), 6.51 (d, 1H), 3.90 (bs, 2H), 2.55 (dd, 2H),
1.83 (m, 1H), 0.91 (d, 6H)

Example 2 Preparation of 3-isobutyl-4- [1-methoxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl] aniline (Compound No. 2-10) 3-isobutyl-4- [ 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl] aniline (1.6 g, 5 mmol) was dissolved in 28% sodium methoxide methanol solution (9.6 g), and the mixture was heated and stirred for 3 hours. . After cooling, the reaction solution was poured into ice water, extracted with ethyl acetate, and washed with water. The extract was dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was separated and purified by silica gel column chromatography (hexane: ethyl acetate = 5: 1) to obtain 1.31 g of the desired product.
Yield: 79%
Physical properties: ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm)]
7.25 (d, 1H), 6.71 (d, 1H), 6.54 (dd, 1H), 3.78 (bs, 2H), 3.43 (s, 3H),
2.81 (d, 2H), 2.13 (m, 1H), 0.92 (d, 6H)

Example 3 Preparation of 3-isobutyl-4- [2,2,2-trifluoro-1- (trifluoromethyl) ethyl] aniline (Compound No. 2-13) 3-isobutyl-4- [1,2, 2,2-tetrafluoro-1- (trifluoromethyl) ethyl] aniline (874 mg, 3 mmol) is dissolved in dimethyl sulfoxide (20 ml), sodium borohydride (340 mg, 9 mmol) is added little by little, and 3 ° C. at 60 ° C. Stir for hours. Ice was added to the reaction solution little by little, and then acetic acid was added dropwise. The reaction mixture was diluted with ethyl acetate and washed 4 times with water. After drying with magnesium sulfate, concentration under reduced pressure gave 830 mg of the desired product.
Yield: 99%
Physical properties: ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm)]
7.30 (d, 1H), 6.57 (dd, 1H), 6.50 (d, 1H), 4.28 (m, 1H), 3.80 (bs, 2H),
2.41 (d, 2H), 1.78 (m, 1H), 0.91 (d, 6H)

Example 4 N- {3-isobutyl-4- [2,2,2-trifluoro-1- (trifluoromethyl) ethyl] phenyl} -3-methylpyrazine-2-carboxylic acid amide (Compound No. 1- 17) Preparation 3-Methylpyrazine-2-carboxylic acid (138 mg, 1 mmol), 3-isobutyl-4- [2,2,2-trifluoro-1- (trifluoromethyl) ethyl] aniline (299 mg, 1 mmol) , 2-chloro-1-methylpyridinium iodide (255 mg, 1 mmol) and triethylamine (303 mg, 3 mmol) were dissolved in tetrahydrofuran (10 ml) and heated to reflux for 3 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was separated and purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1) to obtain 290 mg of the desired product.
Yield: 69%
Physical property: Melting point 133-134 ° C

Example 5 N- {3-Isobutyl-4- [1-methoxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl] phenyl} -3-methylpyrazine-2-carboxylic acid amide (compound No. 1-18) Preparation of 3-isobutyl-4- [1,2,2-trifluoro-1- (trifluoromethyl) ethyl] aniline instead of 3-isobutyl-4- [1-methoxy-2, The target product was obtained by carrying out the reaction for 3 hours in the same manner as in Example 4 except that 2,2-trifluoro-1- (trifluoromethyl) ethyl] aniline was used.
Yield: 56%
Physical property: Melting point 118-119 ° C

Example 6 N- {3-isobutyl-4- [2,2,2-trifluoro-1- (trifluoromethyl) ethyl] phenyl} -3-chloropyrazine-2-carboxylic acid amide (Compound No. 1- 25) Preparation 3-hydroxypyrazine-2-carboxylic acid (154 mg, 1.1 mmol) was dissolved in phosphorus oxychloride (2 ml)), 1 drop of pyridine was added, and the mixture was heated under reflux for 2 hours, concentrated under reduced pressure, and 3-chloro Pyrazine-2-carboxylic acid chloride was obtained. This was added to a solution of 3-isobutyl-4- [2,2,2-trifluoro-1- (trifluoromethyl) ethyl] aniline (299 mg, 1 mmol) and triethylamine (303 mg, 3 mmol) in tetrahydrofuran (10 ml). Heated to reflux for hours. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the obtained residue was separated and purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1) to obtain 200 mg of the desired product.
Yield: 46%
Physical properties: melting point 128-129 ° C

Example 7 N- {3-isobutyl-4- [2,2,2-trifluoro-1- (trifluoromethyl) ethyl] phenyl} -3-methoxypyrazine-2-carboxylic acid amide (Compound No. 1- 28) Preparation The target product was obtained by carrying out the reaction for 3 hours in the same manner as in Example 4 except that 3-methoxypyrazine-2-carboxylic acid was used instead of 3-methylpyrazine-2-carboxylic acid.
Yield: 71%
Physical properties: melting point 135.5-137 ° C.

Example 8 N- {3-isobutyl-4- [1-methoxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl] phenyl} -3-methoxypyrazine-2-carboxylic acid amide (compound No. 1-29) Preparation of 3-isobutyl-4- [2,2,2-trifluoro-1- (trifluoromethyl) ethyl] aniline instead of 3-isobutyl-4- [1-methoxy-2, The target product was obtained by carrying out the reaction for 3 hours in the same manner as in Example 7 except that 2,2-trifluoro-1- (trifluoromethyl) ethyl] aniline was used.
Yield: 50%
Physical property: Melting point 118-119 ° C

Example 9 Preparation of methyl 3-chloromethylpyrazine-2-carboxylate (Compound No. 3-1) Methyl 3-methylpyrazine-2-carboxylate (2.44 g, 16 mmol) was dissolved in chloroform (100 ml). N-chlorosuccinimide (2.14 g, 16 mmol) was added. Subsequently, benzoyl peroxide (110 mg, 70%, 0.32 mmol) was added and heated to reflux for 30 hours. After cooling the reaction solution, insoluble matters are removed by filtration, the filtrate is concentrated under reduced pressure, and the resulting residue is separated and purified by silica gel column chromatography (hexane: ethyl acetate = 1: 1) to obtain the desired product 1. 55 g was obtained.
Yield: 52%
Physical properties: ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm)]
8.75 (d, 1H), 8.68 (d, 1H), 5.14 (s, 2H), 4.06 (s, 3H)

Example 10 Methyl 3-fluoromethylpyrazine-2-carboxylate (Compound No. 3-3
) Methyl 3-chloromethylpyrazine-2-carboxylate (1.55 g, 8.3 mmol) was dissolved in DMSO (30 ml), cesium fluoride (2.52 g, 16.6 mmol) and hexamethylphosphate triamide (0.3 ml) was added, followed by heating and stirring at 140 ° C. for 40 minutes. The reaction mixture was cooled, poured into dilute hydrochloric acid, extracted with ethyl acetate, and washed with water. After drying over magnesium sulfate, the mixture was concentrated under reduced pressure, and the resulting residue was separated and purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1) to obtain 0.13 g of the desired product.
Yield: 9%
Physical properties: ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm)]
8.82 (d, 1H), 8.71 (d, 1H), 5.90 (d, 2H), 4.05 (s, 3H)

Example 11 N- {3-isobutyl-4- [1-methoxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl] phenyl} -3-fluoromethylpyrazine-2-carboxylic acid amide ( Preparation of Compound No. 1-39) Methyl 3-fluoromethylpyrazine-2-carboxylate (390 mg, 2.29 mmol) and 3-isobutyl-4- [1-methoxy-2,2,2-trifluoro-1- (Trifluoromethyl) ethyl] aniline (750 mg, 2.29 mmol) was stirred and 28% sodium methoxide (4.4 g, 22.9 mmol) was added. After heating and stirring at 60 ° C. for 3 hours, the mixture was poured into dilute hydrochloric acid, extracted with ethyl acetate, and washed with water. The extract was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1) to obtain 0.71 g of the desired product.
Yield: 67%
Physical properties: n _D 1.4829 (27.7 ° C.)

Example 12 N-isobutyloxycarbonyl-N- {3-isobutyl-4- [1-methoxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl] phenyl} -3-methylpyrazine-2 Preparation of Carboxylic Acid Amide (Compound No. 1-96) Sodium hydride (32 mg, 60%, 0.8 mmol) was suspended in THF (10 ml) and N- {3-isobutyl-4- [1-methoxy- A solution of 2,2,2-trifluoro-1- (trifluoromethyl) ethyl] phenyl} -3-methylpyrazine-2-carboxylic acid amide (300 mg, 0.67 mmol) in THF (5 ml) was added dropwise. After stirring at room temperature for 30 minutes, a solution of isobutyl chlorocarbonate (110 mg, 0.8 mmol) in THF (2 ml) was added and stirred for 2 hours. The reaction solution was poured into dilute hydrochloric acid, extracted with ethyl acetate, and washed with water. After drying over magnesium sulfate, the mixture was concentrated under reduced pressure, and the resulting residue was separated and purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1) to obtain 0.33 g of the desired product.
Yield: 90%
Physical properties: n _D 1.4814 (23.2 ° C.)

Example 13 N-ethoxymethyl-N- {3-isobutyl-4- [1-methoxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl] phenyl} -3-methylpyrazine-2- Preparation of Carboxylic Acid Amide (Compound No. 1-114) Sodium hydride (32 mg, 60%, 0.8 mmol) was suspended in THF (10 ml) and N- {3-isobutyl-4- [1-methoxy-2] was suspended. , 2,2-trifluoro-1- (trifluoromethyl) ethyl] phenyl} -3-methylpyrazine-2-carboxylic acid amide (300 mg, 0.67 mmol) in THF (5 ml) was added dropwise. After stirring at room temperature for 30 minutes, a solution of chloromethyl ethyl ether (76 mg, 0.8 mmol) in THF (2 ml) was added and stirred for 5 hours. The reaction solution was poured into dilute hydrochloric acid, extracted with ethyl acetate, and washed with water. The extract was dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was separated and purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1) to obtain 0.24 g of the desired product.
Yield: 71%
Physical properties: n _D 1.4899 (23.9 ° C.)

Example 14 N-acetyl-N- {3-isobutyl-4- [1-methoxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl] phenyl} -3-methylpyrazine-2-carboxylic acid Preparation of acid amide (Compound No. 1-106) Sodium hydride (32 mg, 60%, 0.8 mmol) was suspended in THF (10 ml), and N- {3-isobutyl-4- [1-methoxy-2, A solution of 2,2-trifluoro-1- (trifluoromethyl) ethyl] phenyl} -3-methylpyrazine-2-carboxylic acid amide (300 mg, 0.67 mmol) in THF (5 ml) was added dropwise. After stirring at room temperature for 30 minutes, a solution of acetyl chloride (63 mg, 0.8 mmol) in THF (2 ml) was added and stirred overnight. The reaction solution was poured into dilute hydrochloric acid, extracted with ethyl acetate, and washed with water. After drying over magnesium sulfate and concentrating under reduced pressure, the resulting residue was separated and purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1) to obtain 0.10 g of the desired product.
Yield: 30%
Physical properties: n _D 1.4955 (23.0 ° C.)

Example 15 Production of methyl 3-trifluoromethylpyrazine-2-carboxylate (Compound No. 3-4) Methyl 3-chloropyrazine-2-carboxylate (2 g, 11.6 mmol), cuprous iodide (3 .3 g, 17.3 mmol), potassium fluoride (1.34 g, 23 mmol) and methyl chlorodifluoroacetate (3.36 g, 18.2 mmol) were dissolved in DMF (20 ml) and stirred at 115 ° C. for 5 hours under an argon atmosphere. did. The reaction solution was filtered through celite, and the filtrate was diluted with ethyl acetate and washed four times with water. After drying over magnesium sulfate and concentration under reduced pressure, the resulting residue was separated and purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1) to obtain 700 mg of the desired product as a paste.
Yield: 29%
Physical properties: ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm) 8.85 (d, 1H), 8.83 (d, 1H), 4.05 (s, 3H)

Example 16 Preparation of 3-trifluoromethylpyrazine-2-carboxylic acid (Compound No. 3-5) Methyl 3-trifluoromethylpyrazine-2-carboxylate (700 mg, 3.4 mmol) was added to ethanol-water (1: 1, 10 ml), potassium hydroxide (300 mg) was added, and the mixture was heated to reflux for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with water and washed with ethyl acetate. The aqueous layer was acidified with hydrochloric acid, extracted with ethyl acetate, and washed with saturated brine. After drying over magnesium sulfate, the mixture was concentrated under reduced pressure to obtain 409 mg of the desired product as crystals.
Yield: 63%
Physical properties: melting point 130-134 ° C.

Example 17 N- {3-isobutyl-4- [2,2,2-trifluoro-1- (trifluoromethyl) ethyl] phenyl} -3-trifluoromethylpyrazine-2-carboxylic acid amide (1-42 3-trifluoromethyl-2-pyrazinecarboxylic acid (192 mg, 1 mmol), 3-isobutyl-4- [2,2,2-trifluoro-1- (trifluoromethyl) ethyl] aniline (199 mg, 1 mmol) ), 2-chloro-1-methylpyridinium iodide (255 mg, 1 mmol) and triethylamine (303 mg, 3 mmol) were dissolved in tetrahydrofuran (10 ml) and heated to reflux for 2 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1) to obtain 293 mg of the desired product as a paste.
Yield: 62%
Physical properties: n _D 1.4825 (27.7 ° C.)

Although the typical formulation example and test example of this invention are shown below, this invention is not limited to these.
In the preparation examples, “parts” means “parts by weight”.
Formulation Example 1
Compounds listed in Table 1 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts The above components are uniformly mixed and dissolved to prepare an emulsion.
Formulation Example 2
Compounds listed in Table 1 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above is uniformly mixed and ground to obtain a powder.

Formulation Example 3
Compound shown in Table 1 5 parts Bentonite and clay mixed powder 90 parts lignin sulfonate 5 parts The above is uniformly mixed, kneaded with an appropriate amount of water, granulated and dried to form granules.
Formulation Example 4
Compounds listed in Table 1 20 parts Kaolin, synthetic highly dispersed silicic acid 75 parts Polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts The above is uniformly mixed and ground to obtain a wettable powder.

Test Example 1 An acaricidal test against a spider mite (Tetranychus urticae).
A leaf disk with a diameter of 2 cm is made from green beans, placed on a wet filter paper, inoculated with female adults, and then 50 ml of a chemical solution obtained by diluting a drug containing the compound shown in Table 1 as an active ingredient to 500 ppm and 50 ppm. It spread | dispersed uniformly on the turntable and it left still in the thermostatic chamber of 25 degreeC after spreading | spreading. Two days after the drug treatment, the number of dead insects was investigated, the death rate was calculated according to the following formula, and judged according to the following criteria. 2 units in 10 wards in 1 ward.
[Equation 1]

Number of hatched insects in the untreated area-Number of hatched insects in the treated area Corrected death rate (%) = ────────────────── × 100
Number of hatchlings in untreated area

Judgment criteria: A ... Death rate 100%
B ... 99% to 90% death rate
C ... Death rate 89% -80%
D ... Death rate 79% -50%

上記試験の結果、本発明の化合物Ｎｏ．１−２〜１−４、１−６〜１−１０、１−１２〜１−１４、１−１７〜１−３０、１−３９、１−４２、１−４３、１−５１、１−５３、１−５４、１−７３、１−７４、１−７６、１−７７、１−７９、１−８１、１−８２、１−８７、１−９０、１−９６、１−１０４、１−１０６、１−１１２、１−１１４、１−１１７、１−１２５、１−１２７〜１−１２９、１−１３４〜１−１３８、１−１４５、１−１４６、１−１５３〜１−１６０、１−１６３、１−１８９、１−１９９〜１−２１０、１−２１３〜１−２２２の化合物は５００ｐｐｍ及び５０ｐｐｍいずれの濃度においてもＡ活性を示した。一方、対照の両化合物とも５００ｐｐｍの濃度でも殺ダニ活性を示さなかった。

In addition, as a comparative compound, the compound No. described in JP-A-2003-48878. 1-163 and 1-164 were used.

As a result of the above test, the compound No. 1 of the present invention was obtained. 1-2 to 1-4, 1-6 to 1-10, 112 to 1-14, 1-17 to 1-30, 1-39, 1-42, 1-43, 1-51, 1- 53, 1-54, 1-73, 1-74, 1-76, 1-77, 1-79, 1-81, 1-82, 1-87, 1-90, 1-96, 1-104, 1-106, 1-112, 1-114, 1-117, 1-125, 1-127 to 1-129, 1-134 to 1-138, 1-145, 1-146, 1-153 to 1- The compounds of 160, 1-163, 1-189, 1-199-1 to 210, 1-213 to 1-222 showed A activity at both 500 ppm and 50 ppm. On the other hand, both control compounds did not show acaricidal activity even at a concentration of 500 ppm.

Claims (10)

Formula (I)

{Wherein R ¹ is a hydrogen atom, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkylcarbonyl group, a halo C ₁ -C ₆ alkylcarbonyl group, C ₁ -C ₆ alkylcarbonyl C ₁ -C ₆ alkyl group, cyclo C ₃ -C ₆ alkyl group, halocyclo C ₃ -C ₆ alkyl group, cyclo C ₃ -C ₆ alkyl C ₁ -C ₆ alkyl group, halocyclo C ₃ -C ₆ Alkyl C ₁ -C ₆ alkyl group, C ₂ -C ₆ alkenyl group, halo C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, halo C ₂ -C ₆ alkynyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkyl sulfinyl C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl sulfinyl C ₁ -C ₆ alkyl group group, C ₁ -C ₆ alkyl Sulfonyl C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkylsulfonyl C ₁ -C ₆ alkyl group, mono-C ₁ -C ₆ alkylamino C ₁ -C ₆ alkyl group, the same or different and may di C ₁ -C ₆ alkylamino C ₁ -C ₆ alkyl group, phenyl C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxycarbonyl group, halo C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkyl thio group, mono C ₁ -C ₆ alkylaminocarbonyl group, the same or different di C ₁ may be -C ₆ alkylaminocarbonyl groups, C ₁ -C ₆ alkoxycarbonyl C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, a cyano C ₁ -C ₆ alkyl group, a phenyl C ₁ -C ₆ alkyl group , which may be identical or different, a halogen atom, a cyano group, a nitro group, C ₁ -C ₆ al Group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio groups, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, may be the same or different A substituted phenyl C ₁ -C ₆ alkyl group having one or more substituents selected from a di C ₁ -C ₆ alkylamino group or a C ₁ -C ₆ alkoxycarbonyl group on the ring, the same or different Halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ A Kirusurufiniru group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, the same or different and may di C ₁ -C ₆ alkylamino group or a C substituted phenoxycarbonyl groups having 1 or more substituents selected from ₁ -C ₆ alkoxycarbonyl group, a phenylsulfonyl group, which may be identical or different, a halogen atom, a cyano group, a nitro group, C ₁ -C ₆ alkyl Halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkyl Sulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di-C which may be the same or different ₁ -C ₆ alkylamino group or a C ₁ -C ₆ alkoxy Substituted phenylsulfonyl group having one or more substituents selected from aryloxycarbonyl group, the same or different di C ₁ may be -C ₆ alkyl phosphono group, the same or different and may di C ₁ -C ₆ Arukiruhosuho Nochio group, NC ₁ -C ₆ alkyl -NC ₁ -C ₆ alkoxycarbonylamino thio group, NC ₁ -C ₆ alkyl -NC ₁ -C ₆ alkoxycarbonyl C ₁ -C ₆ alkylamino thio group, the same or different A good di-C ₁ -C ₆ alkylaminothio group or a cyclo C ₃ -C ₆ alkylcarbonyl group is shown.
R ² is a hydrogen atom, halogen atom, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, cyano group, hydroxy group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkoxy C ₁ -C ₃ alkoxy group, halo C ₁ -C ₆ alkoxy C ₁ -C ₃ alkoxy groups, C ₁ -C ₆ alkylthio C ₁ -C ₃ alkoxy group, halo C ₁ -C ₆ alkylthio C ₁ -C ₃ alkoxy groups, C ₁ -C ₆ alkylsulfinyl C ₁ -C ₃ alkoxy group, halo C ₁ -C ₆ alkylsulfinyl C ₁ -C ₃ alkoxy groups, C ₁ -C ₆ alkylsulfonyl C ₁ -C ₃ Alkoxy group, halo C ₁ -C ₆ alkylsulfonyl C ₁ -C ₃ alkoxy group, mono C ₁ -C ₆ alkylamino C ₁ -C ₃ alkoxy group, di C ₁ -C ₆ alkylamino C which may be the same or different ₁ -C ₃ alkoxy groups, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkyl Sulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, amino group, mono C ₁ -C ₆ alkylamino group, di C ₁ -C ₆ alkylamino group which may be the same or different Phenoxy group, which may be the same or different, halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo One or more selected from a C ₁ -C ₆ alkylsulfonyl group, a mono C ₁ -C ₆ alkylamino group, a di C ₁ -C ₆ alkylamino group which may be the same or different, or a C ₁ -C ₆ alkoxycarbonyl group Substituted substituted phenoxy group, phenylthio group, the same or different Halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkyl Substituted phenylthio having one or more substituents selected from a sulfonyl group, a mono C ₁ -C ₆ alkylamino group, a di C ₁ -C ₆ alkylamino group or a C ₁ -C ₆ alkoxycarbonyl group which may be the same or different Group, phenylsulfinyl group, which may be the same or different, halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, the same or different A substituted phenylsulfinyl group having one or more substituents selected from a di C ₁ -C ₆ alkylamino group or a C ₁ -C ₆ alkoxycarbonyl group, a phenylsulfonyl group, which may be the same or different, and a halogen atom , cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, a halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C _1- C ₆ alkylamino group, which may be the same or different A substituted phenylsulfonyl group having one or more substituents selected from a di-C ₁ -C ₆ alkylamino group or a C ₁ -C ₆ alkoxycarbonyl group, a phenyl C ₁ -C ₆ alkoxy group or the same or different, Halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group Halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkyl sulfinyl group, halo C ₁ -C ₆ alkyl sulfinyl group, C ₁ -C ₆ alkyl sulfonyl group, halo C ₁ -C ₆ alkyl sulfonyl group, mono C _1- C ₆ alkylamino group, substituted phenyl C ₁ having one or more substituents selected from the same or different di-C ₁ -C ₆ alkylamino group or C ₁ -C ₆ alkoxycarbonyl group on the ring -C shows a ₆ alkoxy group.
G is a C ₂ -C ₁₀ alkyl group, a halo C ₂ -C ₁₀ alkyl group, a C ₃ -C ₁₀ alkenyl group, a halo C ₃ -C ₁₀ alkenyl group, a C ₃ -C ₁₀ alkynyl group, a halo C ₃ -C ₁₀ An alkynyl group, a C ₃ -C ₁₀ cycloalkyl group, which may be the same or different and has one or more substituents selected from a halogen atom, a C ₁ -C ₆ alkyl group or a halo C ₁ -C ₆ alkyl group C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, which may be the same or different, and one or more selected from a halogen atom, a C ₁ -C ₆ alkyl group or a halo C ₁ -C ₆ alkyl group A substituted C ₃ -C ₁₀ cycloalkenyl group, a C ₃ -C ₈ cycloalkyl C ₁ -C ₆ alkyl group or a halo C ₃ -C ₈ cycloalkyl C ₁ -C ₆ alkyl group having the following substituents:
Z represents an oxygen atom or a sulfur atom.
X may be the same or different and each represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group or a halo C ₁ -C ₆ alkyl group.
Y may be the same or different, and may be a hydrogen atom, halogen atom, cyano group, nitro group, hydroxyl group, mercapto group, amino group, carboxyl group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₂ -C ₆ alkenyl group, halo C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, halo C ₂ -C ₆ alkynyl group, tri C ₁ -C ₆ alkylsilyl C ₂ -which may be the same or different C ₆ alkynyl group, phenyl C ₂ -C ₆ alkynyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, hydroxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkyl carbonyl oxy C ₁ -C ₆ alkyl group, C ₃ -C ₆ cycloalkyl group, halo C ₃ -C ₆ cycloalkyl group, C ₃ -C ₆ cycloalkyl C ₁ -C ₆ alkyl group, halo C ₃ -C ₆ cycloalkyl alkyl C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxy group, C C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxy group, a phenyl C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl Group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylsulfinyl C ₁ -C ₆ alkyl group Halo C ₁ -C ₆ alkylsulfinyl C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylsulfonyl C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkylsulfonyl C ₁ -C ₆ alkyl group, mono C ₁ -C ₆ alkylamino group, same or different di C ₁ -C ₆ alkylamino group, phenylamino group, mono C ₁ -C ₆ alkylamino C ₁ -C ₆ alkyl group, same or different di C ₁ -C ₆ alkylamino C ₁ -C ₆ alkyl group, phenyl group, same or different, halogen atom, cyano group, nitro group, C _1- C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, the same or different A substituted phenyl group having one or more substituents selected from a di-C ₁ -C ₆ alkylamino group or a C ₁ -C ₆ alkoxycarbonyl group, a phenoxy group, which may be the same or different, a halogen atom, a cyano group , Nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di-C ₁ -C ₆ alkylamino group or C ₁ -C ₆ alkoxy which may be the same or different A substituted phenoxy group having one or more substituents selected from a carbonyl group, a heterocyclic group, or the same or different, a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ Alkylsulfonyl group, a substituted with one or more substituents selected from mono-C ₁ -C ₆ alkylamino group, the same or different and may di C ₁ -C ₆ alkylamino group or a C ₁ -C ₆ alkoxycarbonyl group A heterocyclic group is shown.
Further, two adjacent Ys on the pyrazine ring can be combined to form a condensed ring, which may be the same or different, and are a halogen atom, a cyano group, a nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C _1- C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, the same or different It may also have one or more substituents selected from good di-C ₁ -C ₆ alkylamino groups or C ₁ -C ₆ alkoxycarbonyl groups. m and n represent an integer of 1 to 3. } The substituted pyrazinecarboxylic acid anilide derivative | guide_body represented by these, and its salts. The substituted pyrazinecarboxylic acid anilide derivative and salts thereof according to claim 1, wherein G is a C ₂ -C ₁₀ alkyl group.   The substituted pyrazinecarboxylic acid anilide derivative and salts thereof according to claim 1 or 2, wherein X is a hydrogen atom.   The substituted pyrazinecarboxylic acid anilide derivative and salts thereof according to any one of claims 1 to 3, wherein Z is a group represented by an oxygen atom.   An agricultural and horticultural agent comprising the substituted pyrazinecarboxylic acid anilide derivative or a salt thereof according to any one of claims 1 to 4 as an active ingredient.   The agricultural and horticultural agent according to claim 5, wherein the agricultural and horticultural agent is an agricultural or horticultural insecticide or an acaricide.   A method for using an agricultural and horticultural agent characterized by treating an effective amount of the agricultural and horticultural agent according to claim 5 or 6 on a target plant or soil in order to control pests from useful plants. Formula (II)

{Wherein R ¹ is a hydrogen atom, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkylcarbonyl group, a halo C ₁ -C ₆ alkylcarbonyl group, C ₁ -C ₆ alkylcarbonyl C ₁ -C ₆ alkyl group, cyclo C ₃ -C ₆ alkyl group, halocyclo C ₃ -C ₆ alkyl group, cyclo C ₃ -C ₆ alkyl C ₁ -C ₆ alkyl group, halocyclo C ₃ -C ₆ Alkyl C ₁ -C ₆ alkyl group, C ₂ -C ₆ alkenyl group, halo C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, halo C ₂ -C ₆ alkynyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkyl sulfinyl C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl sulfinyl C ₁ -C ₆ alkyl group group, C ₁ -C ₆ alkyl Sulfonyl C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkylsulfonyl C ₁ -C ₆ alkyl group, mono-C ₁ -C ₆ alkylamino C ₁ -C ₆ alkyl group, the same or different and may di C ₁ -C ₆ alkylamino C ₁ -C ₆ alkyl group, phenyl C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxycarbonyl group, halo C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkyl thio group, mono C ₁ -C ₆ alkylaminocarbonyl group, the same or different di C ₁ may be -C ₆ alkylaminocarbonyl groups, C ₁ -C ₆ alkoxycarbonyl C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, a cyano C ₁ -C ₆ alkyl group, a phenyl C ₁ -C ₆ alkyl group , which may be identical or different, a halogen atom, a cyano group, a nitro group, C ₁ -C ₆ al Group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio groups, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, may be the same or different A substituted phenyl C ₁ -C ₆ alkyl group having one or more substituents selected from a di C ₁ -C ₆ alkylamino group or a C ₁ -C ₆ alkoxycarbonyl group on the ring, the same or different Halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ A Kirusurufiniru group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, the same or different and may di C ₁ -C ₆ alkylamino group or a C substituted phenoxycarbonyl groups having 1 or more substituents selected from ₁ -C ₆ alkoxycarbonyl group, a phenylsulfonyl group, which may be identical or different, a halogen atom, a cyano group, a nitro group, C ₁ -C ₆ alkyl Halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkyl Sulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di-C which may be the same or different ₁ -C ₆ alkylamino group or a C ₁ -C ₆ alkoxy Substituted phenylsulfonyl group having one or more substituents selected from aryloxycarbonyl group, the same or different di C ₁ may be -C ₆ alkyl phosphono group, the same or different and may di C ₁ -C ₆ Arukiruhosuho Nochio group, NC ₁ -C ₆ alkyl -NC ₁ -C ₆ alkoxycarbonylamino thio group, NC ₁ -C ₆ alkyl -NC ₁ -C ₆ alkoxycarbonyl C ₁ -C ₆ alkylamino thio group, the same or different A good di-C ₁ -C ₆ alkylaminothio group or a cyclo C ₃ -C ₆ alkylcarbonyl group is shown.
R ² is a hydrogen atom, halogen atom, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, cyano group, hydroxy group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkoxy C ₁ -C ₃ alkoxy group, halo C ₁ -C ₆ alkoxy C ₁ -C ₃ alkoxy groups, C ₁ -C ₆ alkylthio C ₁ -C ₃ alkoxy group, halo C ₁ -C ₆ alkylthio C ₁ -C ₃ alkoxy groups, C ₁ -C ₆ alkylsulfinyl C ₁ -C ₃ alkoxy group, halo C ₁ -C ₆ alkylsulfinyl C ₁ -C ₃ alkoxy groups, C ₁ -C ₆ alkylsulfonyl C ₁ -C ₃ Alkoxy group, halo C ₁ -C ₆ alkylsulfonyl C ₁ -C ₃ alkoxy group, mono C ₁ -C ₆ alkylamino C ₁ -C ₃ alkoxy group, di C ₁ -C ₆ alkylamino C which may be the same or different ₁ -C ₃ alkoxy groups, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkyl Sulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, amino group, mono C ₁ -C ₆ alkylamino group, di C ₁ -C ₆ alkylamino group which may be the same or different Phenoxy group, which may be the same or different, halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo One or more selected from a C ₁ -C ₆ alkylsulfonyl group, a mono C ₁ -C ₆ alkylamino group, a di C ₁ -C ₆ alkylamino group which may be the same or different, or a C ₁ -C ₆ alkoxycarbonyl group Substituted substituted phenoxy group, phenylthio group, the same or different Halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkyl Substituted phenylthio having one or more substituents selected from a sulfonyl group, a mono C ₁ -C ₆ alkylamino group, a di C ₁ -C ₆ alkylamino group or a C ₁ -C ₆ alkoxycarbonyl group which may be the same or different Group, phenylsulfinyl group, which may be the same or different, halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, the same or different A substituted phenylsulfinyl group having one or more substituents selected from a di C ₁ -C ₆ alkylamino group or a C ₁ -C ₆ alkoxycarbonyl group, a phenylsulfonyl group, which may be the same or different, and a halogen atom , cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, a halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C _1- C ₆ alkylamino group, which may be the same or different A substituted phenylsulfonyl group having one or more substituents selected from a di-C ₁ -C ₆ alkylamino group or a C ₁ -C ₆ alkoxycarbonyl group, a phenyl C ₁ -C ₆ alkoxy group or the same or different, Halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group Halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkyl sulfinyl group, halo C ₁ -C ₆ alkyl sulfinyl group, C ₁ -C ₆ alkyl sulfonyl group, halo C ₁ -C ₆ alkyl sulfonyl group, mono C _1- C ₆ alkylamino group, substituted phenyl C ₁ having one or more substituents selected from the same or different di-C ₁ -C ₆ alkylamino group or C ₁ -C ₆ alkoxycarbonyl group on the ring -C shows a ₆ alkoxy group.
G is a C ₂ -C ₁₀ alkyl group, a halo C ₂ -C ₁₀ alkyl group, a C ₃ -C ₁₀ alkenyl group, a halo C ₃ -C ₁₀ alkenyl group, a C ₃ -C ₁₀ alkynyl group, a halo C ₃ -C ₁₀ An alkynyl group, a C ₃ -C ₁₀ cycloalkyl group, which may be the same or different and has one or more substituents selected from a halogen atom, a C ₁ -C ₆ alkyl group or a halo C ₁ -C ₆ alkyl group C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, which may be the same or different, and one or more selected from a halogen atom, a C ₁ -C ₆ alkyl group or a halo C ₁ -C ₆ alkyl group A substituted C ₃ -C ₁₀ cycloalkenyl group, a C ₃ -C ₈ cycloalkyl C ₁ -C ₆ alkyl group or a halo C ₃ -C ₈ cycloalkyl C ₁ -C ₆ alkyl group having the following substituents:
X may be the same or different and each represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group or a halo C ₁ -C ₆ alkyl group. n shows the integer of 1-3. } Substituted aniline derivatives and salts thereof.   The substituted aniline derivative and salts thereof according to claim 8, wherein X is a hydrogen atom. General formula (III ')

{Wherein Y 'may be the same or different and represents a halo C ₁ -C ₆ alkyl group, R ¹ ' represents a hydrogen atom or a C ₁ -C ₆ alkyl group, and m represents an integer of 1 to 3. Show. } The substituted pyrazine carboxylic acid derivative represented by these, and its salts.