JP2016145155A - Phthalamide derivative, agricultural and horticultural insecticide containing the same, and application method thereof - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a compound for an agricultural and horticultural insecticide.SOLUTION: There is provided a phthalamide derivative represented by the general formula (I) or salts thereof. In the formula (1), Xrepresents a halogen atom or the like, Xrepresents a hydrogen atom or the like, Y represents a hydrogen atom, a halogen atom, an alkyl group or the like, Z, Zand Zmay be same or different and represent a nitrogen atom, CH, C-Yor C-A-Q, where at least one of Z, Zand Zis C-A-Q, A represents a linear or branched (C-C) alkylene group, Q represents a specific condensed heterocyclic group, Rrepresents a (C-C) alkylthio (C-C) alkyl group or the like, and Rand Rrepresent a hydrogen atom or the like.SELECTED DRAWING: None

Description

  The present invention relates to an agricultural and horticultural insecticide containing a novel phthalamide derivative containing an imidazopyridine ring group or a salt thereof as an active ingredient, and a method of using the same.

Despite the development of various agricultural and horticultural insecticides, the damage caused by pests in agriculture and horticultural crop production is still large, and there are problems such as the generation of resistant pests against existing drugs. Therefore, development of new agricultural and horticultural insecticides is desired. Further, various labor-saving application methods are required due to the aging of farmers, and the creation of agricultural and horticultural insecticides having characteristics suitable for these application methods is also required.
It is described that certain phthalamide derivatives in Patent Documents 1, 2, 3 and 4 and certain imidazopyridine derivatives in Patent Document 5 are useful as insecticides, respectively. However, there remains a need for the development of new agro-horticultural insecticides of this line with higher activity and / or a broader insecticidal spectrum.

International Publication No. 2004-080984 Pamphlet International Publication No. 2005-095351 Pamphlet International Publication No. 2006-053643 Pamphlet International Publication No. 2010-012442 Pamphlet International Publication 2012-086848 Pamphlet

  Therefore, an object of the present invention is to provide a new compound for a novel agricultural and horticultural insecticide.

  As a result of intensive studies in view of the above problems, the present inventors have found that the phthalamide derivative or its salt, which has not been known so far, has excellent characteristics that a conventional similar compound does not have, and As a result of research, the present invention has been completed.

［式中、Ｘ^１は、
(a1) ハロゲン原子；
(a2)（Ｃ_１〜Ｃ_８）アルキル基；
(a3)（Ｃ_１〜Ｃ_８）ハロアルキル基；
(a4)（Ｃ_１〜Ｃ_８）アルコキシ基；
(a5)（Ｃ_１〜Ｃ_８）ハロアルコキシ基；
(a6)（Ｃ_１〜Ｃ_８）アルキルチオ基；
(a7)（Ｃ_１〜Ｃ_８）ハロアルキルチオ基；
(a8)（Ｃ_１〜Ｃ_８）アルキルスルフィニル基；
(a9)（Ｃ_１〜Ｃ_８）ハロアルキルスルフィニル基；
(a10)（Ｃ_１〜Ｃ_８）アルキルスルホニル基；又は
(a11)（Ｃ_１〜Ｃ_８）ハロアルキルスルホニル基を示し、
Ｘ^２は、
(b1) 水素原子；
(b2) ハロゲン原子；
(b3)（Ｃ_１〜Ｃ_８）アルキル基；
(b4)（Ｃ_１〜Ｃ_８）ハロアルキル基；
(b5)（Ｃ_１〜Ｃ_８）アルコキシ基；又は
(b6)（Ｃ_１〜Ｃ_８）ハロアルコキシ基を示し、
Ｙは、
(c1) 水素原子；
(c2) ハロゲン原子；
(c3) シアノ基；
(c4)（Ｃ_１〜Ｃ_８）アルキル基；
(c5)（Ｃ_１〜Ｃ_８）ハロアルキル基；
(c6)（Ｃ_１〜Ｃ_８）アルコキシ基；
(c7)（Ｃ_１〜Ｃ_８）ハロアルコキシ基；
(c8)（Ｃ_１〜Ｃ_８）アルキルチオ基；
(c9)（Ｃ_１〜Ｃ_８）ハロアルキルチオ基；
(c10)（Ｃ_１〜Ｃ_８）アルキルスルフィニル基；
(c11)（Ｃ_１〜Ｃ_８）ハロアルキルスルフィニル基；、
(c12)（Ｃ_１〜Ｃ_８）アルキルスルホニル基；又は
(c13)（Ｃ_１〜Ｃ_８）ハロアルキルスルホニル基を示し、
Ｙ¹は、
(d1) ハロゲン原子；
(d2)（Ｃ_１−Ｃ_８）アルキル基；
(d3)（Ｃ_１−Ｃ_８）ハロアルキル基；
(d4)（Ｃ_１−Ｃ_８）アルコキシ基；又は
(d5)（Ｃ_１−Ｃ_８）ハロアルコキシ基を示し、
Ｚ^１、Ｚ^２、及びＺ^３は、同一又は異なっても良く、窒素原子、ＣＨ、Ｃ−Ｙ¹、又はＣ−Ａ−Ｑ（但し、Ｃ−Ａ−Ｑは、Ｚ^１、Ｚ^２、又はＺ^３のいずれかの１つと結合するもののみであっても良い）を示す。
Ａは、直鎖又は分岐鎖状の（Ｃ_１−Ｃ_８）アルキレン基を示し、
Ｑは、以下に挙げる群から選択される縮合複素環基を示す。

「式中、・で印を付けた箇所が、Ａと結合し、
ここでＷ^２は、
(e1) 水素原子；
(e2) ハロゲン原子；
(e3) シアノ基；
(e4) ホルミル基
(e5) シアノ（Ｃ_１〜Ｃ_８）アルキル基；
(e6)（Ｃ_１〜Ｃ_８）アルキル基；
(e7)（Ｃ_２〜Ｃ_８）アルケニル基；
(e8)（Ｃ_２〜Ｃ_８）アルキニル基；
(e9)（Ｃ_２〜Ｃ_８）ハロアルケニル基；
(e10)（Ｃ_３〜Ｃ_８）シクロアルキル基；
(e11)（Ｃ_３〜Ｃ_８）シクロアルキル（Ｃ_１〜Ｃ_８）アルコキシ基；
(e12)（Ｃ_１〜Ｃ_８）アルコキシ基；
(e13)（Ｃ_１〜Ｃ_８）アルコキシ（Ｃ_１〜Ｃ_８）アルキル基；
(e14)（Ｃ_１〜Ｃ_８）ハロアルキル基；
(e15)（Ｃ_１〜Ｃ_８）ハロアルコキシ基；
(e16)（Ｃ_３〜Ｃ_８）ハロシクロアルキル基；
(e17)（Ｃ_３〜Ｃ_８）ハロシクロアルキル（Ｃ_１〜Ｃ_８）アルキル基；
(e18)（Ｃ_１〜Ｃ_８）アルキルチオ基；
(e19)（Ｃ_１〜Ｃ_８）アルキルスルフィニル基；
(e20)（Ｃ_１〜Ｃ_８）アルキルスルホニル基；
(e21)（Ｃ_１〜Ｃ_８）アルキルチオ（Ｃ_１〜Ｃ_８）アルキル基；
(e22)（Ｃ_１〜Ｃ_８）アルキルスルフィニル（Ｃ_１〜Ｃ_８）アルキル基；
(e23)（Ｃ_１〜Ｃ_８）アルキルスルホニル（Ｃ_１〜Ｃ_８）アルキル基；
(e24)（Ｃ_１〜Ｃ_８）ハロアルキルチオ基；
(e25)（Ｃ_１〜Ｃ_８）ハロアルキルスルフィニル基；
(e26)（Ｃ_１〜Ｃ_８）ハロアルキルスルホニル基；
(e27)（Ｃ_１〜Ｃ_８）アルコキシカルボニル基；
(e28)（Ｃ_２〜Ｃ_８）アルケニルオキシカルボニル基；
(e29)（Ｃ_１〜Ｃ_８）アルコキシカルボニル（Ｃ_１〜Ｃ_８）アルキル基；
(e30)（Ｃ_１〜Ｃ_８）アルキルカルボニル基；
(e31)（Ｃ_３〜Ｃ_８）シクロアルキルカルボニル基；
(e32) Ｒ^４ (Ｒ^５)Ｎ基（式中、Ｒ^４及びＲ^５は、同一又は異なっても良く水素原子、（Ｃ_１−Ｃ_８）アルキル基、（Ｃ_３−Ｃ_８）シクロアルキル基、（Ｃ_２−Ｃ_８）アルケニル基、（Ｃ_２−Ｃ_８）アルキニル基、（Ｃ_３−Ｃ_８）シクロアルキル（Ｃ_１−Ｃ_８）アルキル基、（Ｃ_１−Ｃ_８）ハロアルキル基、（Ｃ_３−Ｃ_８）ハロシクロアルキル基、（Ｃ_１−Ｃ_８）アルキルカルボニル基、（Ｃ_１−Ｃ_８）アルコキシカルボニル基、（Ｃ_１−Ｃ_８）アルコキシ（Ｃ_１−Ｃ_８）アルキル基、アリール基、同一又は異なっても良く (a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)（Ｃ_１−Ｃ_８）アルキル基、(f)（Ｃ_１−Ｃ_８）ハロアルキル基、(g)（Ｃ_１−Ｃ_８）アルコキシ基、(h)（Ｃ_１−Ｃ_８）ハロアルコキシ基、(i)（Ｃ_３−Ｃ_８）シクロアルキル（Ｃ_１−Ｃ_８）アルコキシ基、(j)（Ｃ_１−Ｃ_８）アルキルチオ基、(k)（Ｃ_１−Ｃ_８）ハロアルキルチオ基、(l)（Ｃ_１−Ｃ_８）アルキルスルフィニル基、(m)（Ｃ_１−Ｃ_８）ハロアルキルスルフィニル基、(n)（Ｃ_１−Ｃ_８）アルキルスルホニル基、(o)（Ｃ_１−Ｃ_８）ハロアルキルスルホニル基、(p)（Ｃ_１−Ｃ_８）アルキルカルボニル基、(q)カルボキシル基、(r)（Ｃ_１−Ｃ_８）アルコキシカルボニル基、及び(s)フェノキシ基から選択される１〜５の置換基を環上に有するアリール基、複素環基、同一又は異なっても良く (a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)（Ｃ_１−Ｃ_８）アルキル基、(f)（Ｃ_１−Ｃ_８）ハロアルキル基、(g)（Ｃ_１−Ｃ_８）アルコキシ基、(h)（Ｃ_１−Ｃ_８）ハロアルコキシ基、(i)（Ｃ₃−Ｃ_８）シクロアルキル（Ｃ_１−Ｃ_８）アルコキシ基、(j)（Ｃ_１−Ｃ_８）アルキルチオ基、(k)（Ｃ_１−Ｃ_８）ハロアルキルチオ基、(l)（Ｃ_１−Ｃ_８）アルキルスルフィニル基、(m)（Ｃ_１−Ｃ_８）ハロアルキルスルフィニル基、(n)（Ｃ_１−Ｃ_８）アルキルスルホニル基、(o)（Ｃ_１−Ｃ_８）ハロアルキルスルホニル基、(p)（Ｃ_１−Ｃ_８）アルキルカルボニル基、(q)カルボキシル基、(r)（Ｃ_１−Ｃ_８）アルコキシカルボニル基、及び(s)フェノキシ基から選択される１〜５の置換基を環上に有する複素環基を示す。）；
(e33) Ｒ^４ (Ｒ^５)Ｎカルボニル基（式中、Ｒ^４及びＲ^５は前記に同じ。）；
(e34) Ｒ^４ (Ｒ^５)ＮＣＯＮ（Ｒ^５）基（式中、Ｒ^４及びＲ^５は前記に同じ。）；
(e35) Ｒ^４ (Ｒ^５)Ｎ（Ｃ_１−Ｃ_８）アルキル基（式中、Ｒ^４及びＲ^５は前記に同じ。）；
(e36) アリール基；
(e37) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)（Ｃ_１−Ｃ_８）アルキル基、(f)（Ｃ_１−Ｃ_８）ハロアルキル基、(g)（Ｃ_１−Ｃ_８）アルコキシ基、(h)（Ｃ_１−Ｃ_８）ハロアルコキシ基、(i)（Ｃ_３−Ｃ_８）シクロアルキル（Ｃ_１−Ｃ_８）アルコキシ基、(j)（Ｃ_１−Ｃ_８）アルキルチオ基、(k)（Ｃ_１−Ｃ_８）ハロアルキルチオ基、(l)（Ｃ_１−Ｃ_８）アルキルスルフィニル基、(m)（Ｃ_１−Ｃ_８）ハロアルキルスルフィニル基、(n)（Ｃ_１−Ｃ_８）アルキルスルホニル基、(o)（Ｃ_１−Ｃ_８）ハロアルキルスルホニル基、(p)（Ｃ_１−Ｃ_８）アルキルカルボニル基、(q)カルボキシル基、(r)（Ｃ_１−Ｃ_８）アルコキシカルボニル基、及び(s)フェノキシ基から選択される１〜５の置換基を環上に有するアリール基；
(e38) アリール（Ｃ_１−Ｃ_８）アルキル基；
(e39) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)（Ｃ_１−Ｃ_８）アルキル基、(f)（Ｃ_１−Ｃ_８）ハロアルキル基、(g)（Ｃ_１−Ｃ_８）アルコキシ基、(h)（Ｃ_１−Ｃ_８）ハロアルコキシ基、(i)（Ｃ_３−Ｃ_８）シクロアルキル（Ｃ_１−Ｃ_８）アルコキシ基、(j)（Ｃ_１−Ｃ_８）アルキルチオ基、(k)（Ｃ_１−Ｃ_８）ハロアルキルチオ基、(l)（Ｃ_１−Ｃ_８）アルキルスルフィニル基、(m)（Ｃ_１−Ｃ_８）ハロアルキルスルフィニル基、(n)（Ｃ_１−Ｃ_８）アルキルスルホニル基、(o)（Ｃ_１−Ｃ_８）ハロアルキルスルホニル基、(p)（Ｃ_１−Ｃ_８）アルキルカルボニル基、(q)カルボキシル基、(r)（Ｃ_１−Ｃ_８）アルコキシカルボニル基、及び(s)フェノキシ基から選択される１〜５の置換基を環上に有するアリール（Ｃ_１−Ｃ_８）アルキル基；
(e40) 複素環基；（明細書の記載で対応しました。）
(e41) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)（Ｃ_１−Ｃ_８）アルキル基、(f)（Ｃ_１−Ｃ_８）ハロアルキル基、(g)（Ｃ_１−Ｃ_８）アルコキシ基、(h)（Ｃ_１−Ｃ_８）ハロアルコキシ基、(i)（Ｃ_３−Ｃ_８）シクロアルキル（Ｃ_１−Ｃ_８）アルコキシ基、(j)（Ｃ_１−Ｃ_８）アルキルチオ基、(k)（Ｃ_１−Ｃ_８）ハロアルキルチオ基、(l)（Ｃ_１−Ｃ_８）アルキルスルフィニル基、(m)（Ｃ_１−Ｃ_８）ハロアルキルスルフィニル基、(n)（Ｃ_１−Ｃ_８）アルキルスルホニル基、(o)（Ｃ_１−Ｃ_８）ハロアルキルスルホニル基、(p)（Ｃ_１−Ｃ_８）アルキルカルボニル基、(q)カルボキシル基、(r)（Ｃ_１−Ｃ_８）アルコキシカルボニル基、(s)フェノキシ基、及び(t)フェニルメトキシカルボニル基から選択される１〜５の置換基を環上に有する複素環基；
(e42) 複素環（Ｃ_１−Ｃ_８）オキシ基；
(e43) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)（Ｃ_１−Ｃ_８）アルキル基、(f)（Ｃ_１−Ｃ_８）ハロアルキル基、(g)（Ｃ_１−Ｃ_８）アルコキシ基、(h)（Ｃ_１−Ｃ_８）ハロアルコキシ基、(i)（Ｃ_３−Ｃ_８）シクロアルキル（Ｃ_１−Ｃ_８）アルコキシ基、(j)（Ｃ_１−Ｃ_８）アルキルチオ基、(k)（Ｃ_１−Ｃ_８）ハロアルキルチオ基、(l)（Ｃ_１−Ｃ_８）アルキルスルフィニル基、(m)（Ｃ_１−Ｃ_８）ハロアルキルスルフィニル基、(n)（Ｃ_１−Ｃ_８）アルキルスルホニル基、(o)（Ｃ_１−Ｃ_８）ハロアルキルスルホニル基、(p)（Ｃ_１−Ｃ_８）アルキルカルボニル基、(q)カルボキシル基、(r)（Ｃ_１−Ｃ_８）アルコキシカルボニル基、及び(s)フェノキシ基から選択される１〜５の置換基を環上に有する複素環オキシ基；
(e44) 複素環（Ｃ_１−Ｃ_８）アルキル基；又は
(e45) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)（Ｃ_１−Ｃ_８）アルキル基、(f)（Ｃ_１−Ｃ_８）ハロアルキル基、(g)（Ｃ_１−Ｃ_８）アルコキシ基、(h)（Ｃ_１−Ｃ_８）ハロアルコキシ基、(i)（Ｃ_３−Ｃ_８）シクロアルキル（Ｃ_１−Ｃ_８）アルコキシ基、(j)（Ｃ_１−Ｃ_８）アルキルチオ基、(k)（Ｃ_１−Ｃ_８）ハロアルキルチオ基、(l)（Ｃ_１−Ｃ_８）アルキルスルフィニル基、(m)（Ｃ_１−Ｃ_８）ハロアルキルスルフィニル基、(n)（Ｃ_１−Ｃ_８）アルキルスルホニル基、(o)（Ｃ_１−Ｃ_８）ハロアルキルスルホニル基、(p)（Ｃ_１−Ｃ_８）アルキルカルボニル基、(q)カルボキシル基、(r)（Ｃ_１−Ｃ_８）アルコキシカルボニル基、及び(s)フェノキシ基から選択される１〜５の置換基を環上に有する複素環（Ｃ_１−Ｃ_８）アルキル基を示す。
Ｗ^３は、
(f1) 水素原子；
(f2) ハロゲン原子；
(f3) シアノ基；
(f4) ホルミル基
(f5) シアノ（Ｃ_１〜Ｃ_８）アルキル基；
(f6)（Ｃ_１〜Ｃ_８）アルキル基；
(f7)（Ｃ_２〜Ｃ_８）アルケニル基；
(f8)（Ｃ_２〜Ｃ_８）アルキニル基；
(f9)（Ｃ_２〜Ｃ_８）ハロアルケニル基；
(f10)（Ｃ_３〜Ｃ_８）シクロアルキル基；
(f11)（Ｃ_３〜Ｃ_８）シクロアルキル（Ｃ_１〜Ｃ_８）アルコキシ基；
(f12)（Ｃ_１〜Ｃ_８）アルコキシ基；
(f13)（Ｃ_１〜Ｃ_８）アルコキシ（Ｃ_１〜Ｃ_８）アルキル基；
(f14)（Ｃ_１〜Ｃ_８）ハロアルキル基；
(f15)（Ｃ_１〜Ｃ_８）ハロアルコキシ基；
(f16)（Ｃ_３〜Ｃ_８）ハロシクロアルキル基；
(f17)（Ｃ_３〜Ｃ_８）ハロシクロアルキル（Ｃ_１〜Ｃ_８）アルキル基；
(f18)（Ｃ_１〜Ｃ_８）アルキルチオ基；
(f19)（Ｃ_１〜Ｃ_８）アルキルスルフィニル基；
(f20)（Ｃ_１〜Ｃ_８）アルキルスルホニル基；
(f21)（Ｃ_１〜Ｃ_８）アルキルチオ（Ｃ_１〜Ｃ_８）アルキル基；
(f22)（Ｃ_１〜Ｃ_８）アルキルスルフィニル（Ｃ_１〜Ｃ_８）アルキル基；
(f23)（Ｃ_１〜Ｃ_８）アルキルスルホニル（Ｃ_１〜Ｃ_８）アルキル基；
(f24)（Ｃ_１〜Ｃ_８）ハロアルキルチオ基；
(f25)（Ｃ_１〜Ｃ_８）ハロアルキルスルフィニル基；
(f26)（Ｃ_１〜Ｃ_８）ハロアルキルスルホニル基；
(f27)（Ｃ_１〜Ｃ_８）アルコキシカルボニル基；
(f28)（Ｃ_２〜Ｃ_８）アルケニルオキシカルボニル基；
(f29)（Ｃ_１〜Ｃ_８）アルコキシカルボニル（Ｃ_１〜Ｃ_８）アルキル基；
(f30)（Ｃ_１〜Ｃ_８）アルキルカルボニル基；
(f31)（Ｃ_３〜Ｃ_８）シクロアルキルカルボニル基；
(f32) Ｒ^４ (Ｒ^５)Ｎカルボニル基（式中、Ｒ^４及びＲ^５は前記に同じ。）；
(f33) Ｒ^４ (Ｒ^５)Ｎスルホニル基（式中、Ｒ^４及びＲ^５は前記に同じ。）；
(f34) アリール基；
(f35) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)（Ｃ_１−Ｃ_８）アルキル基、(f)（Ｃ_１−Ｃ_８）ハロアルキル基、(g)（Ｃ_１−Ｃ_８）アルコキシ基、(h)（Ｃ_１−Ｃ_８）ハロアルコキシ基、(i)（Ｃ_３−Ｃ_８）シクロアルキル（Ｃ_１−Ｃ_８）アルコキシ基、(j)（Ｃ_１−Ｃ_８）アルキルチオ基、(k)（Ｃ_１−Ｃ_８）ハロアルキルチオ基、(l)（Ｃ_１−Ｃ_８）アルキルスルフィニル基、(m)（Ｃ_１−Ｃ_８）ハロアルキルスルフィニル基、(n)（Ｃ_１−Ｃ_８）アルキルスルホニル基、(o)（Ｃ_１−Ｃ_８）ハロアルキルスルホニル基、(p)（Ｃ_１−Ｃ_８）アルキルカルボニル基、(q)カルボキシル基、(r)（Ｃ_１−Ｃ_８）アルコキシカルボニル基、及び(s)フェノキシ基から選択される１〜５の置換基を環上に有するアリール基；
(f36) アリール（Ｃ_１−Ｃ_８）アルキル基；
(f37) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)（Ｃ_１−Ｃ_８）アルキル基、(f)（Ｃ_１−Ｃ_８）ハロアルキル基、(g)（Ｃ_１−Ｃ_８）アルコキシ基、(h)（Ｃ_１−Ｃ_８）ハロアルコキシ基、(i)（Ｃ_３−Ｃ_８）シクロアルキル（Ｃ_１−Ｃ_８）アルコキシ基、(j)（Ｃ_１−Ｃ_８）アルキルチオ基、(k)（Ｃ_１−Ｃ_８）ハロアルキルチオ基、(l)（Ｃ_１−Ｃ_８）アルキルスルフィニル基、(m)（Ｃ_１−Ｃ_８）ハロアルキルスルフィニル基、(n)（Ｃ_１−Ｃ_８）アルキルスルホニル基、(o)（Ｃ_１−Ｃ_８）ハロアルキルスルホニル基、(p)（Ｃ_１−Ｃ_８）アルキルカルボニル基、(q)カルボキシル基、(r)（Ｃ_１−Ｃ_８）アルコキシカルボニル基、及び(s)フェノキシ基から選択される１〜５の置換基を環上に有するアリール（Ｃ_１−Ｃ_８）アルキル基；
(f38) 複素環基；
(f39) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)（Ｃ_１−Ｃ_８）アルキル基、(f)（Ｃ_１−Ｃ_８）ハロアルキル基、(g)（Ｃ_１−Ｃ_８）アルコキシ基、(h)（Ｃ_１−Ｃ_８）ハロアルコキシ基、(i)（Ｃ_３−Ｃ_８）シクロアルキル（Ｃ_１−Ｃ_８）アルコキシ基、(j)（Ｃ_１−Ｃ_８）アルキルチオ基、(k)（Ｃ_１−Ｃ_８）ハロアルキルチオ基、(l)（Ｃ_１−Ｃ_８）アルキルスルフィニル基、(m)（Ｃ_１−Ｃ_８）ハロアルキルスルフィニル基、(n)（Ｃ_１−Ｃ_８）アルキルスルホニル基、(o)（Ｃ_１−Ｃ_８）ハロアルキルスルホニル基、(p)（Ｃ_１−Ｃ_８）アルキルカルボニル基、(q)カルボキシル基、(r)（Ｃ_１−Ｃ_８）アルコキシカルボニル基、及び(s)フェノキシ基から選択される１〜５の置換基を環上に有する複素環基；
(f40) 複素環カルボニル基；
(f41) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)（Ｃ_１−Ｃ_８）アルキル基、(f)（Ｃ_１−Ｃ_８）ハロアルキル基、(g)（Ｃ_１−Ｃ_８）アルコキシ基、(h)（Ｃ_１−Ｃ_８）ハロアルコキシ基、(i)（Ｃ_３−Ｃ_８）シクロアルキル（Ｃ_１−Ｃ_８）アルコキシ基、(j)（Ｃ_１−Ｃ_８）アルキルチオ基、(k)（Ｃ_１−Ｃ_８）ハロアルキルチオ基、(l)（Ｃ_１−Ｃ_８）アルキルスルフィニル基、(m)（Ｃ_１−Ｃ_８）ハロアルキルスルフィニル基、(n)（Ｃ_１−Ｃ_８）アルキルスルホニル基、(o)（Ｃ_１−Ｃ_８）ハロアルキルスルホニル基、(p)（Ｃ_１−Ｃ_８）アルキルカルボニル基、(q)カルボキシル基、(r)（Ｃ_１−Ｃ_８）アルコキシカルボニル基、及び(s)フェノキシ基から選択される１〜５の置換基を環上に有する複素環カルボニル基；
(f42) 複素環（Ｃ_１−Ｃ_８）アルキル基；又は
(f43) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)（Ｃ_１−Ｃ_８）アルキル基、(f)（Ｃ_１−Ｃ_８）ハロアルキル基、(g)（Ｃ_１−Ｃ_８）アルコキシ基、(h)（Ｃ_１−Ｃ_８）ハロアルコキシ基、(i)（Ｃ_３−Ｃ_８）シクロアルキル（Ｃ_１−Ｃ_８）アルコキシ基、(j)（Ｃ_１−Ｃ_８）アルキルチオ基、(k)（Ｃ_１−Ｃ_８）ハロアルキルチオ基、(l)（Ｃ_１−Ｃ_８）アルキルスルフィニル基、(m)（Ｃ_１−Ｃ_８）ハロアルキルスルフィニル基、(n)（Ｃ_１−Ｃ_８）アルキルスルホニル基、(o)（Ｃ_１−Ｃ_８）ハロアルキルスルホニル基、(p)（Ｃ_１−Ｃ_８）アルキルカルボニル基、(q)カルボキシル基、(r)（Ｃ_１−Ｃ_８）アルコキシカルボニル基、及び(s)フェノキシ基から選択される１〜５の置換基を環上に有する複素環（Ｃ_１−Ｃ_８）アルキル基を示す。
Ｗ^４、Ｗ^５、Ｗ^６、及びＷ^７は、同一又は異なっても良く、
(g1) 水素原子；
(g2) ハロゲン原子；
(g3) シアノ基；
(g4) ホルミル基
(g5)（Ｃ_１〜Ｃ_８）アルキル基；
(g6)（Ｃ_１〜Ｃ_８）ハロアルキル基；
(g7)（Ｃ_１〜Ｃ_８）アルコキシ基；又は
(g8)（Ｃ_１〜Ｃ_８）ハロアルコキシ基を示す。
Ｒ^１は、
(h1)（Ｃ_１〜Ｃ_８）アルキル基；
(h2)（Ｃ_２〜Ｃ_８）アルケニル基；
(h3)（Ｃ_２〜Ｃ_８）アルキニル基；
(h4)（Ｃ_３〜Ｃ_８）シクロアルキル基；
(h5) シアノ（Ｃ_１〜Ｃ_８）アルキル基；
(h6)（Ｃ_３〜Ｃ_８）シクロアルキル（Ｃ_１〜Ｃ_８）アルキル基；
(h7) ヒドロキシ（Ｃ_１〜Ｃ_８）アルキル基；
(h8)（Ｃ_１〜Ｃ_８）アルコキシ（Ｃ_１〜Ｃ_８）アルキル基；
(h9)（Ｃ₁〜Ｃ_８）アルキルチオ（Ｃ_１〜Ｃ_８）アルキル基；
(h10)（Ｃ_１〜Ｃ_８）アルキルスルフィニル（Ｃ_１〜Ｃ_８）アルキル基；
(h11)（Ｃ_１〜Ｃ_８）アルキルスルホニル（Ｃ_１〜Ｃ_８）アルキル基；
(h12) アリール（Ｃ_１〜Ｃ_８）アルキル基；
(h13) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)（Ｃ_１−Ｃ_８）アルキル基、(f)（Ｃ_１−Ｃ_８）ハロアルキル基、(g)（Ｃ_１−Ｃ_８）アルコキシ基、(h)（Ｃ_１−Ｃ_８）ハロアルコキシ基、(i)（Ｃ_３−Ｃ_８）シクロアルキル（Ｃ_１−Ｃ_８）アルコキシ基、(j)（Ｃ_１−Ｃ_８）アルキルチオ基、(k)（Ｃ_１−Ｃ_８）ハロアルキルチオ基、(l)（Ｃ_１−Ｃ_８）アルキルスルフィニル基、(m)（Ｃ_１−Ｃ_８）ハロアルキルスルフィニル基、(n)（Ｃ_１−Ｃ_８）アルキルスルホニル基、(o)（Ｃ_１−Ｃ_８）ハロアルキルスルホニル基、(p)（Ｃ_１−Ｃ_８）アルキルカルボニル基、(q)カルボキシル基、(r)（Ｃ_１−Ｃ_８）アルコキシカルボニル基、(s)Ｒ^４ (Ｒ^５) Ｎカルボニル基（式中、Ｒ^４及びＲ^５は前記に同じ。）、及び(t)フェノキシ基から選択される１〜５の置換基を環上に有するアリール（Ｃ_１〜Ｃ_８）アルキル基；
(h14)Ｒ^４ (Ｒ^５) ＮＣＯ_２（Ｃ_１〜Ｃ_８）アルキル基（式中、Ｒ^４及びＲ^５は前記に同じ。）
(h15)Ｒ^４ (Ｒ^５) ＮＣＯ（Ｃ_１〜Ｃ_８）アルキル基（式中、Ｒ^４及びＲ^５は前記に同じ。）；又は、
(h16)Ｒ^４ (Ｒ^５) ＮＣＯ（Ｒ^４）Ｎ（Ｃ_１−Ｃ_８）アルキル基（式中、Ｒ^４及びＲ^５は前記に同じ。）を示す。」。
Ｒ^２は、
(i1) 水素原子；
(i2)（Ｃ_１−Ｃ_８）アルキル基；
(i3)（Ｃ_３−Ｃ_８）シクロアルキル基； 若しくは
(i4)（Ｃ_３−Ｃ_８）シクロアルキル（Ｃ_１−Ｃ_８）アルキル基を示し、又は
(i5)Ｒ^１とＲ^２が結合して、一つの窒素原子を含み、さらに酸素原子、窒素原子、及び硫黄原子から選ばれる１〜２個の同一又は異なっても良いヘテロ原子を含んでいても良い５〜８員の飽和含窒素複素環を形成することもできる。
Ｒ^３は、
(j1) 水素原子；
(j2)（Ｃ_１−Ｃ_８）アルキル基；
(j3)（Ｃ_３−Ｃ_８）シクロアルキル基；又は
(j4)（Ｃ_３−Ｃ_８）シクロアルキル（Ｃ_１−Ｃ_８）アルキル基；
を示す。］で表されるフタルアミド誘導体、又はその塩類（但し、Ｎ^１‐{２‐クロロ‐４‐［（６‐ヘプタフルオロイソプロピル）‐２‐（トリフルオロメチル）‐１Ｈ‐イミダゾ［４，５‐Ｃ］ピリジン‐１‐イル）メチル］フェニル}‐３‐ヨード‐Ｎ^２‐（２−メチル‐1‐（メチルチオ）プロパン‐２‐イル）フタルアミドを除く。）。 That is, the present invention relates to at least the following inventions [1] to [6]:
[1] General formula (1):

[Wherein X ¹ is
(a1) a halogen atom;
_{(a2) (C 1 ~C 8} ) alkyl group;
_{(a3) (C 1 ~C 8} ) haloalkyl group;
_{(a4) (C 1 ~C 8} ) alkoxy groups;
_{(a5) (C 1 ~C 8} ) haloalkoxy group;
_{(a6) (C 1 ~C 8} ) alkylthio group;
_{(a7) (C 1 ~C 8} ) haloalkylthio group;
(a8) a (C ₁ -C ₈ ) alkylsulfinyl group;
_{(a9) (C 1 ~C 8} ) haloalkylsulfinyl group;
_{(a10) (C 1 ~C 8} ) alkylsulfonyl group; or
(a11) represents a (C ₁ -C ₈ ) haloalkylsulfonyl group,
X ² is,
(b1) a hydrogen atom;
(b2) a halogen atom;
_{(b3) (C 1 ~C 8} ) alkyl group;
_{(b4) (C 1 ~C 8} ) haloalkyl group;
_{(b5) (C 1 ~C 8} ) alkoxy group; or
(b6) represents a (C ₁ -C ₈ ) haloalkoxy group,
Y is
(c1) hydrogen atom;
(c2) a halogen atom;
(c3) a cyano group;
_{(c4) (C 1 ~C 8} ) alkyl group;
_{(c5) (C 1 ~C 8} ) haloalkyl group;
_{(c6) (C 1 ~C 8} ) alkoxy groups;
_{(c7) (C 1 ~C 8} ) haloalkoxy group;
_{(c8) (C 1 ~C 8} ) alkylthio group;
_{(c9) (C 1 ~C 8} ) haloalkylthio group;
_{(c10) (C 1 ~C 8} ) alkylsulfinyl group;
_{(c11) (C 1 ~C 8} ) haloalkylsulfinyl groups;,
_{(c12) (C 1 ~C 8} ) alkylsulfonyl group; or
(c13) represents a (C ₁ -C ₈ ) haloalkylsulfonyl group,
Y ¹ is
(d1) a halogen atom;
(d2) a (C ₁ -C ₈ ) alkyl group;
_{(d3) (C 1 -C 8} ) haloalkyl group;
_{(d4) (C 1 -C 8} ) alkoxy group; or
(d5) represents a (C ₁ -C ₈ ) haloalkoxy group,
Z ¹ , Z ² , and Z ³ may be the same or different, and are a nitrogen atom, CH, C—Y ¹ , or C—AQ (where C—AQ is Z ¹ , Z ² , Or only one that binds to any one of Z ³ ).
A represents a linear or branched (C ₁ -C ₈ ) alkylene group,
Q represents a fused heterocyclic group selected from the group listed below.

“In the formula, the part marked with.
Where W ² is
(e1) hydrogen atom;
(e2) a halogen atom;
(e3) a cyano group;
(e4) Formyl group
(e5) a cyano (C ₁ -C ₈ ) alkyl group;
_{(e6) (C 1 ~C 8} ) alkyl group;
_{(e7) (C 2 ~C 8} ) alkenyl group;
_{(e8) (C 2 ~C 8} ) alkynyl group;
_{(e9) (C 2 ~C 8} ) haloalkenyl group;
_{(e10) (C 3 ~C 8} ) cycloalkyl group;
_{(e11) (C 3 ~C 8} ) cycloalkyl _(C 1 _{~C 8)} alkoxy groups;
_{(e12) (C 1 ~C 8} ) alkoxy groups;
_{(e13) (C 1 ~C 8} ) alkoxy _(C 1 _{~C 8)} alkyl group;
_{(e14) (C 1 ~C 8} ) haloalkyl group;
_{(e15) (C 1 ~C 8} ) haloalkoxy group;
_{(e16) (C 3 ~C 8} ) halocycloalkyl group;
_{(e17) (C 3 ~C 8} ) halocycloalkyl _(C 1 _{~C 8)} alkyl group;
_{(e18) (C 1 ~C 8} ) alkylthio group;
_{(e19) (C 1 ~C 8} ) alkylsulfinyl group;
_{(e20) (C 1 ~C 8} ) alkylsulfonyl group;
(e21) a (C ₁ -C ₈ ) alkylthio (C ₁ -C ₈ ) alkyl group;
(e22) a (C ₁ -C ₈ ) alkylsulfinyl (C ₁ -C ₈ ) alkyl group;
(e23) a (C ₁ -C ₈ ) alkylsulfonyl (C ₁ -C ₈ ) alkyl group;
_{(e24) (C 1 ~C 8} ) haloalkylthio group;
_{(e25) (C 1 ~C 8} ) haloalkylsulfinyl group;
_{(e26) (C 1 ~C 8} ) haloalkylsulfonyl groups;
_{(e27) (C 1 ~C 8} ) alkoxycarbonyl group;
_{(e28) (C 2 ~C 8} ) alkenyloxycarbonyl group;
(e29) a (C ₁ -C ₈ ) alkoxycarbonyl (C ₁ -C ₈ ) alkyl group;
_{(e30) (C 1 ~C 8} ) alkylcarbonyl group;
_{(e31) (C 3 ~C 8} ) cycloalkyl group;
(e32) R ⁴ (R ⁵ ) N group (wherein R ⁴ and R ⁵ may be the same or different, a hydrogen atom, (C ₁ -C ₈ ) alkyl group, (C ₃ -C ₈ ) cycloalkyl) _{group, (C} 2 -C _{8) alkenyl, (C} 2 -C _{8) alkynyl, (C} 3 -C ₈₎ cycloalkyl _(C 1 -C ₈₎ alkyl _{groups, (C} 1 -C ₈₎ haloalkyl group , _(C 3 -C ₈₎ halocycloalkyl _{group, (C} 1 -C ₈₎ alkylcarbonyl _{group, (C} 1 -C ₈₎ alkoxycarbonyl _{group, (C} 1 -C ₈₎ alkoxy _(C 1 _-C 8) Alkyl group, aryl group, which may be the same or different (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C ₁ -C ₈ ) alkyl group, ( _{f) (C} 1 -C ₈₎ haloalkyl _{group, (g) (C 1 -C} 8) alkoxy groups, (h) _{(C 1} - ₈₎ haloalkoxy _{group, (i) (C 3 -C} 8) cycloalkyl _(C 1 -C ₈₎ alkoxy _{group, (j) (C 1 -C} 8) alkylthio _{group, (k) (C 1 -C} 8 ) Haloalkylthio group, (l) (C ₁ -C ₈ ) alkylsulfinyl group, (m) (C ₁ -C ₈ ) haloalkylsulfinyl group, (n) (C ₁ -C ₈ ) alkylsulfonyl group, (o) (C ₁ -C ₈ ) haloalkylsulfonyl group, (p) (C ₁ -C ₈ ) alkylcarbonyl group, (q) carboxyl group, (r) (C ₁ -C ₈ ) alkoxycarbonyl group, and (s) phenoxy An aryl group having 1 to 5 substituents selected from a group, a heterocyclic group, which may be the same or different (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) Formyl group, (e) (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈₎ alkoxy _{groups, (h) (C 1 -C} 8) haloalkoxy _{group, (i) (C 3 -C} 8) cycloalkyl _(C 1 -C ₈₎ alkoxy group, (j) _{(C 1} -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C} 1 -C ₈₎ haloalkylsulfinyl group, ( _{n) (C} 1 -C ₈₎ alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl _{group, (p) (C 1 -C} 8) alkylcarbonyl group, (q) a carboxyl group, (r) A heterocyclic group having 1 to 5 substituents selected from (C ₁ -C ₈ ) alkoxycarbonyl group and (s) phenoxy group on the ring. );
(e33) R ⁴ (R ⁵ ) N carbonyl group (wherein R ⁴ and R ⁵ are the same as above);
(e34) R ⁴ (R ⁵ ) NCON (R ⁵ ) group (wherein R ⁴ and R ⁵ are the same as above);
(e35) R ⁴ (R ⁵ ) N (C ₁ -C ₈ ) alkyl group (wherein R ⁴ and R ⁵ are the same as above);
(e36) an aryl group;
(e37) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈ ) alkoxy group, (h) (C ₁ -C ₈ ) haloalkoxy group, (i) (C ₃ -C ₈ ) cycloalkyl ( C ₁ -C ₈₎ alkoxy group, _{(j) (C} 1 -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C 1 -C 8} ) haloalkylsulfinyl _{group, (n) (C 1 -C} 8) alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl group, _(p) (C 1 -C ₈₎ alkylcarbonyl group, (q) a carboxyl _{group, (r) (C 1 -C} 8) alkoxycarbonyl group, and (s). 1 to be selected from a phenoxy group An aryl group having a substituent on the ring;
(e38) aryl _(C 1 -C ₈₎ alkyl group;
(e39) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈ ) alkoxy group, (h) (C ₁ -C ₈ ) haloalkoxy group, (i) (C ₃ -C ₈ ) cycloalkyl ( C ₁ -C ₈₎ alkoxy group, _{(j) (C} 1 -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C 1 -C 8} ) haloalkylsulfinyl _{group, (n) (C 1 -C} 8) alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl group, _(p) (C 1 -C ₈₎ alkylcarbonyl group, (q) a carboxyl _{group, (r) (C 1 -C} 8) alkoxycarbonyl group, and (s). 1 to be selected from a phenoxy group Aryl having substituents on the ring _(C 1 -C ₈₎ alkyl group;
(e40) Heterocyclic group; (Supported in the description)
(e41) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈ ) alkoxy group, (h) (C ₁ -C ₈ ) haloalkoxy group, (i) (C ₃ -C ₈ ) cycloalkyl ( C ₁ -C ₈₎ alkoxy group, _{(j) (C} 1 -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C 1 -C 8} ) haloalkylsulfinyl _{group, (n) (C 1 -C} 8) alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl group, _(p) (C 1 -C ₈₎ alkylcarbonyl group, (q) a carboxyl _{group, (r) (C 1 -C} 8) alkoxycarbonyl group, (s) a phenoxy group, and (t) phenyl methoxide A heterocyclic group having from 1 to 5 substituents selected from a carbonyl group on the ring;
(e42) a heterocyclic (C ₁ -C ₈ ) oxy group;
(e43) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈ ) alkoxy group, (h) (C ₁ -C ₈ ) haloalkoxy group, (i) (C ₃ -C ₈ ) cycloalkyl ( C ₁ -C ₈₎ alkoxy group, _{(j) (C} 1 -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C 1 -C 8} ) haloalkylsulfinyl _{group, (n) (C 1 -C} 8) alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl group, _(p) (C 1 -C ₈₎ alkylcarbonyl group, (q) a carboxyl _{group, (r) (C 1 -C} 8) alkoxycarbonyl group, and (s). 1 to be selected from a phenoxy group Heterocyclic oxy group having a substituent on the ring;
(e44) a heterocyclic (C ₁ -C ₈ ) alkyl group; or
(e45) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈ ) alkoxy group, (h) (C ₁ -C ₈ ) haloalkoxy group, (i) (C ₃ -C ₈ ) cycloalkyl ( C ₁ -C ₈₎ alkoxy group, _{(j) (C} 1 -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C 1 -C 8} ) haloalkylsulfinyl _{group, (n) (C 1 -C} 8) alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl group, _(p) (C 1 -C ₈₎ alkylcarbonyl group, (q) a carboxyl _{group, (r) (C 1 -C} 8) alkoxycarbonyl group, and (s). 1 to be selected from a phenoxy group The substituents showing a heterocyclic _(C 1 -C ₈₎ alkyl groups having on the ring.
W ³ is,
(f1) hydrogen atom;
(f2) a halogen atom;
(f3) a cyano group;
(f4) Formyl group
(f5) a cyano (C ₁ -C ₈ ) alkyl group;
_{(f6) (C 1 ~C 8} ) alkyl group;
_{(f7) (C 2 ~C 8} ) alkenyl group;
_{(f8) (C 2 ~C 8} ) alkynyl group;
_{(f9) (C 2 ~C 8} ) haloalkenyl group;
_{(f10) (C 3 ~C 8} ) cycloalkyl group;
_{(f11) (C 3 ~C 8} ) cycloalkyl _(C 1 _{~C 8)} alkoxy groups;
_{(f12) (C 1 ~C 8} ) alkoxy groups;
_{(f13) (C 1 ~C 8} ) alkoxy _(C 1 _{~C 8)} alkyl group;
_{(f14) (C 1 ~C 8} ) haloalkyl group;
_{(f15) (C 1 ~C 8} ) haloalkoxy group;
_{(f16) (C 3 ~C 8} ) halocycloalkyl group;
_{(f17) (C 3 ~C 8} ) halocycloalkyl _(C 1 _{~C 8)} alkyl group;
_{(f18) (C 1 ~C 8} ) alkylthio group;
_{(f19) (C 1 ~C 8} ) alkylsulfinyl group;
_{(f20) (C 1 ~C 8} ) alkylsulfonyl group;
(f21) a (C ₁ -C ₈ ) alkylthio (C ₁ -C ₈ ) alkyl group;
(f22) a (C ₁ -C ₈ ) alkylsulfinyl (C ₁ -C ₈ ) alkyl group;
(f23) a (C ₁ -C ₈ ) alkylsulfonyl (C ₁ -C ₈ ) alkyl group;
_{(f24) (C 1 ~C 8} ) haloalkylthio group;
(f25) a (C ₁ -C ₈ ) haloalkylsulfinyl group;
_{(f26) (C 1 ~C 8} ) haloalkylsulfonyl groups;
_{(f27) (C 1 ~C 8} ) alkoxycarbonyl group;
_{(f28) (C 2 ~C 8} ) alkenyloxycarbonyl group;
_{(f29) (C 1 ~C 8} ) alkoxycarbonyl _(C 1 _{~C 8)} alkyl group;
_{(f30) (C 1 ~C 8} ) alkylcarbonyl group;
_{(f31) (C 3 ~C 8} ) cycloalkyl group;
(f32) R ⁴ (R ⁵ ) N carbonyl group (wherein R ⁴ and R ⁵ are the same as above);
(f33) R ⁴ (R ⁵ ) N sulfonyl group (wherein R ⁴ and R ⁵ are the same as above);
(f34) an aryl group;
(f35) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈ ) alkoxy group, (h) (C ₁ -C ₈ ) haloalkoxy group, (i) (C ₃ -C ₈ ) cycloalkyl ( C ₁ -C ₈₎ alkoxy group, _{(j) (C} 1 -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C 1 -C 8} ) haloalkylsulfinyl _{group, (n) (C 1 -C} 8) alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl group, _(p) (C 1 -C ₈₎ alkylcarbonyl group, (q) a carboxyl _{group, (r) (C 1 -C} 8) alkoxycarbonyl group, and (s). 1 to be selected from a phenoxy group An aryl group having a substituent on the ring;
(f36) aryl _(C 1 -C ₈₎ alkyl group;
(f37) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈ ) alkoxy group, (h) (C ₁ -C ₈ ) haloalkoxy group, (i) (C ₃ -C ₈ ) cycloalkyl ( C ₁ -C ₈₎ alkoxy group, _{(j) (C} 1 -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C 1 -C 8} ) haloalkylsulfinyl _{group, (n) (C 1 -C} 8) alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl group, _(p) (C 1 -C ₈₎ alkylcarbonyl group, (q) a carboxyl _{group, (r) (C 1 -C} 8) alkoxycarbonyl group, and (s). 1 to be selected from a phenoxy group Aryl having substituents on the ring _(C 1 -C ₈₎ alkyl group;
(f38) a heterocyclic group;
(f39) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈ ) alkoxy group, (h) (C ₁ -C ₈ ) haloalkoxy group, (i) (C ₃ -C ₈ ) cycloalkyl ( C ₁ -C ₈₎ alkoxy group, _{(j) (C} 1 -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C 1 -C 8} ) haloalkylsulfinyl _{group, (n) (C 1 -C} 8) alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl group, _(p) (C 1 -C ₈₎ alkylcarbonyl group, (q) a carboxyl _{group, (r) (C 1 -C} 8) alkoxycarbonyl group, and (s). 1 to be selected from a phenoxy group Heterocyclic group having a substituent on the ring;
(f40) heterocyclic carbonyl group;
(f41) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈ ) alkoxy group, (h) (C ₁ -C ₈ ) haloalkoxy group, (i) (C ₃ -C ₈ ) cycloalkyl ( C ₁ -C ₈₎ alkoxy group, _{(j) (C} 1 -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C 1 -C 8} ) haloalkylsulfinyl _{group, (n) (C 1 -C} 8) alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl group, _(p) (C 1 -C ₈₎ alkylcarbonyl group, (q) a carboxyl _{group, (r) (C 1 -C} 8) alkoxycarbonyl group, and (s). 1 to be selected from a phenoxy group Heterocyclic carbonyl group having a substituent on the ring;
(f42) a heterocyclic (C ₁ -C ₈ ) alkyl group; or
(f43) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈ ) alkoxy group, (h) (C ₁ -C ₈ ) haloalkoxy group, (i) (C ₃ -C ₈ ) cycloalkyl ( C ₁ -C ₈₎ alkoxy group, _{(j) (C} 1 -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C 1 -C 8} ) haloalkylsulfinyl _{group, (n) (C 1 -C} 8) alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl group, _(p) (C 1 -C ₈₎ alkylcarbonyl group, (q) a carboxyl _{group, (r) (C 1 -C} 8) alkoxycarbonyl group, and (s). 1 to be selected from a phenoxy group The substituents showing a heterocyclic _(C 1 -C ₈₎ alkyl groups having on the ring.
W ⁴ , W ⁵ , W ⁶ , and W ⁷ may be the same or different,
(g1) hydrogen atom;
(g2) a halogen atom;
(g3) a cyano group;
(g4) Formyl group
_{(g5) (C 1 ~C 8} ) alkyl group;
_{(g6) (C 1 ~C 8} ) haloalkyl group;
_{(g7) (C 1 ~C 8} ) alkoxy group; or
_(g8) shows a _(C 1 _{~C 8)} haloalkoxy group.
R ¹ is
_{(h1) (C 1 ~C 8} ) alkyl group;
_{(h2) (C 2 ~C 8} ) alkenyl group;
_{(h3) (C 2 ~C 8} ) alkynyl group;
_{(h4) (C 3 ~C 8} ) cycloalkyl group;
(h5) a cyano (C ₁ -C ₈ ) alkyl group;
_{(h6) (C 3 ~C 8} ) cycloalkyl _(C 1 _{~C 8)} alkyl group;
(h7) hydroxy _(C 1 _{~C 8)} alkyl group;
(h8) (C ₁ -C ₈ ) alkoxy (C ₁ -C ₈ ) alkyl groups;
(h9) a (C ₁ -C ₈ ) alkylthio (C ₁ -C ₈ ) alkyl group;
(h10) a (C ₁ -C ₈ ) alkylsulfinyl (C ₁ -C ₈ ) alkyl group;
(h11) a (C ₁ -C ₈ ) alkylsulfonyl (C ₁ -C ₈ ) alkyl group;
(h12) aryl _(C 1 _{~C 8)} alkyl group;
(h13) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈ ) alkoxy group, (h) (C ₁ -C ₈ ) haloalkoxy group, (i) (C ₃ -C ₈ ) cycloalkyl ( C ₁ -C ₈₎ alkoxy group, _{(j) (C} 1 -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C 1 -C 8} ) haloalkylsulfinyl _{group, (n) (C 1 -C} 8) alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl group, _(p) (C 1 -C ₈₎ alkylcarbonyl group, (q) a carboxyl group, _{(r) (C} 1 -C ₈₎ alkoxycarbonyl ^{group, (s) R 4 (R} 5) N group (wherein, . ⁴ and ^{R 5} are the same as defined above), and (t) aryl having from 1 to 5 substituents on the ring which is selected from a phenoxy group _(C 1 -C ₈₎ alkyl group;
(h14) R ⁴ (R ⁵ ) NCO ₂ (C ₁ -C ₈ ) alkyl group (wherein R ⁴ and R ⁵ are the same as above).
(h15) R ⁴ (R ⁵ ) NCO (C ₁ -C ₈ ) alkyl group (wherein R ⁴ and R ⁵ are the same as above); or
(h16) R ⁴ (R ⁵ ) NCO (R ⁴ ) N (C ₁ -C ₈ ) alkyl group (wherein R ⁴ and R ⁵ are the same as above). "
R ² is
(i1) hydrogen atom;
_{(i2) (C 1 -C 8} ) alkyl group;
_{(i3) (C 3 -C 8} ) cycloalkyl group; or
_{(i4) (C 3 -C 8} ) a cycloalkyl _(C 1 -C ₈₎ alkyl group, or
(i5) R ¹ and R ² are bonded to each other and contain one nitrogen atom, and further contain 1 to 2 identical or different heteroatoms selected from an oxygen atom, a nitrogen atom and a sulfur atom. Also good 5-8 membered saturated nitrogen-containing heterocycles can be formed.
R ³ is
(j1) hydrogen atom;
_{(j2) (C 1 -C 8} ) alkyl group;
_{(j3) (C 3 -C 8} ) cycloalkyl group; or
_{(j4) (C 3 -C 8} ) cycloalkyl _(C 1 -C ₈₎ alkyl group;
Indicates. ] Or a salt thereof (provided that N ^1- {2-chloro-4-[(6-heptafluoroisopropyl) -2- (trifluoromethyl) -1H-imidazo [4,5-C except (2-methyl-1- (methylthio) propan-2-yl) phthalamide -] pyridin-1-yl) methyl] phenyl} -3-iodo ^-N 2. ).

[2] The phthalamide derivative or salt thereof according to [1] represented by the following:
X ¹ is
(a1) a halogen atom;
_{(a6) (C 1 ~C 8} ) alkylthio group;
(a8) a (C ₁ -C ₈ ) alkylsulfinyl group; or
(a10) a (C ₁ -C ₈ ) alkylsulfonyl group, and X ² is
(b1) is a hydrogen atom,
Y is
(c1) hydrogen atom;
(c2) a halogen atom;
(c3) a cyano group;
_{(c4) (C 1 ~C 8} ) alkyl group;
_{(c6) (C 1 ~C 8} ) alkoxy groups;
_{(c8) (C 1 ~C 8} ) alkylthio group; or
(c10) a (C ₁ -C ₈ ) alkylsulfinyl group,
W ² is,
(e1) hydrogen atom;
(e3) a cyano group;
_{(e6) (C 1 ~C 8} ) alkyl group;
_{(e10) (C 3 ~C 8} ) cycloalkyl group;
_{(e11) (C 3 ~C 8} ) cycloalkyl _(C 1 _{~C 8)} alkoxy groups;
_{(e12) (C 1 ~C 8} ) alkoxy groups;
_{(e13) (C 1 ~C 8} ) alkoxy _(C 1 _{~C 8)} alkyl group;
_{(e14) (C 1 ~C 8} ) haloalkyl group;
_{(e15) (C 1 ~C 8} ) haloalkoxy group;
_{(e18) (C 1 ~C 8} ) alkylthio group;
_{(e19) (C 1 ~C 8} ) alkylsulfinyl group;
_{(e20) (C 1 ~C 8} ) alkylsulfonyl group;
_{(e27) (C 1 ~C 8} ) alkoxycarbonyl group;
(e32) R ⁴ (R ⁵ ) N group (wherein R ⁴ and R ⁵ may be the same or different, a hydrogen atom, (C ₁ -C ₈ ) alkyl group, (C ₃ -C ₈ ) cycloalkyl) A group, (C ₁ -C ₈ ) alkylcarbonyl group, (C ₁ -C ₈ ) alkoxycarbonyl group, or (C ₁ -C ₈ ) alkoxy (C ₁ -C ₈ ) alkyl group);
(e33) R ⁴ (R ⁵ ) N carbonyl group (wherein R ⁴ and R ⁵ are the same as above);
(e34) R ⁴ (R ⁵ ) NCON (R ⁵ ) group (wherein R ⁴ and R ⁵ are the same as above);
(e36) an aryl group;
(e37) aryl group which may be the same or different, and (a) an aryl group having 1 to 5 substituents selected from a halogen atom and (f) (C ₁ -C ₈ ) haloalkyl group on the ring;
(e40) a heterocyclic group;
(e41) may be identical or different, a heterocyclic group having a _{(r) (C 1 -C 8} ) alkoxycarbonyl group, and (t) 1 to 5 substituents selected from phenylmethoxy carbonyl group on the ring; Or
(e42) a heterocyclic (C ₁ -C ₈ ) oxy group,
W ³ is,
(f1) hydrogen atom;
(f5) a cyano (C ₁ -C ₈ ) alkyl group;
_{(f6) (C 1 ~C 8} ) alkyl group;
_{(f7) (C 2 ~C 8} ) alkenyl group;
_{(f8) (C 2 ~C 8} ) alkynyl group;
_{(f10) (C 3 ~C 8} ) cycloalkyl group;
_{(f11) (C 3 ~C 8} ) cycloalkyl _(C 1 _{~C 8)} alkoxy groups;
_{(f13) (C 1 ~C 8} ) alkoxy _(C 1 _{~C 8)} alkyl group;
_{(f14) (C 1 ~C 8} ) haloalkyl group;
(f21) a (C ₁ -C ₈ ) alkylthio (C ₁ -C ₈ ) alkyl group;
(f22) a (C ₁ -C ₈ ) alkylsulfinyl (C ₁ -C ₈ ) alkyl group;
(f23) a (C ₁ -C ₈ ) alkylsulfonyl (C ₁ -C ₈ ) alkyl group;
_{(f27) (C 1 ~C 8} ) alkoxycarbonyl group;
_{(f29) (C 1 ~C 8} ) alkoxycarbonyl _(C 1 _{~C 8)} alkyl group;
_{(f30) (C 1 ~C 8} ) alkylcarbonyl group;
(f32) R ⁴ (R ⁵ ) N carbonyl group (wherein R ⁴ and R ⁵ are the same as above);
(f33) R ⁴ (R ⁵ ) N sulfonyl group (wherein R ⁴ and R ⁵ are the same as above);
(f38) a heterocyclic group;
(f40) a heterocyclic carbonyl group; or
(f42) a heterocyclic (C ₁ -C ₈ ) alkyl group,
W ⁴ , W ⁵ , W ⁶ , and W ⁷ may be the same or different,
(g1) a hydrogen atom; or
(g6) a (C ₁ -C ₈ ) haloalkyl group,
R ¹ is
_{(h1) (C 1 ~C 8} ) alkyl group;
_{(h4) (C 3 ~C 8} ) cycloalkyl group;
(h5) a cyano (C ₁ -C ₈ ) alkyl group;
(h7) hydroxy _(C 1 _{~C 8)} alkyl group;
(h8) (C ₁ -C ₈ ) alkoxy (C ₁ -C ₈ ) alkyl groups;
(h9) a (C ₁ -C ₈ ) alkylthio (C ₁ -C ₈ ) alkyl group;
(h10) a (C ₁ -C ₈ ) alkylsulfinyl (C ₁ -C ₈ ) alkyl group;
(h11) a (C ₁ -C ₈ ) alkylsulfonyl (C ₁ -C ₈ ) alkyl group;
(h12) aryl _(C 1 _{~C 8)} alkyl group; or
(h14) R ⁴ (R ⁵ ) NCO ₂ (C ₁ -C ₈ ) alkyl group (wherein R ⁴ and R ⁵ are the same as above),
R ² is
(i1) a hydrogen atom; or
(i2) is a (C ₁ -C ₈ ) alkyl group; or
(i5) R ¹ and R ² are bonded to each other and contain one nitrogen atom, and further contain 1-2 identical or different heteroatoms selected from an oxygen atom, a nitrogen atom, and a sulfur atom. Can form a good 5- to 8-membered saturated nitrogen-containing heterocycle,
R ³ is
(j1) a hydrogen atom; or
(j2) a (C ₁ -C ₈ ) alkyl group.

[3] The phthalamide derivative or the salt thereof according to [2] represented by the following:
X ¹ is
(a1) a halogen atom; or
(a10) a (C ₁ -C ₈ ) alkylsulfonyl group, and X ² is
(b1) is a hydrogen atom,
Y is
(c1) hydrogen atom;
(c2) a halogen atom; or
_{(c4) (C 1 ~C 8} ) alkyl group,
W ² is,
_{(e12) (C 1 ~C 8} ) alkoxy group; or
(e14) a (C ₁ -C ₈ ) haloalkyl group,
W ³ is,
(f1) hydrogen atom;
_{(f6) (C 1 ~C 8} ) alkyl group;
_{(f8) (C 2 ~C 8} ) alkynyl; or
(f14) a (C ₁ -C ₈ ) haloalkyl group,
W ⁴ , W ⁵ , W ⁶ , and W ⁷ may be the same or different,
(g1) a hydrogen atom; or
(g6) a (C ₁ -C ₈ ) haloalkyl group,
R ¹ is
(h9) a (C ₁ -C ₈ ) alkylthio (C ₁ -C ₈ ) alkyl group;
(h10) a (C ₁ -C ₈ ) alkylsulfinyl (C ₁ -C ₈ ) alkyl group; or
_{(h11) (C 1 ~C 8} ) alkylsulfonyl _(C 1 _{~C 8)} alkyl group,
R ² is
(i1) is a hydrogen atom,
R ³ is
(j1) A hydrogen atom.

［式中、Ｙ、Ｚ^１、Ｚ^２、Ｚ^３、Ａ及びＱは請求項１における定義と同じ。］で表されるフタルアミド誘導体の中間体にかかるアニリン誘導体、又はその塩類。 [4] An agricultural and horticultural insecticide comprising the phthalamide derivative or a salt thereof according to any one of [1] to [3] as an active ingredient.
[5] A method for using an agricultural and horticultural insecticide characterized by treating a plant or soil with the phthalamide derivative or salt thereof according to any one of [1] to [3] as an active ingredient of an agricultural and horticultural insecticide .
[6] A method for using an agricultural and horticultural insecticide characterized by treating a plant or soil with the phthalamide derivative or salt thereof according to any one of [1] to [3] as an active ingredient of an agricultural and horticultural insecticide .
[7] General formula (3):

[Wherein, Y, Z ¹ , Z ² , Z ³ , A and Q are the same as defined in claim 1. ] The aniline derivative concerning the intermediate of the phthalamide derivative represented by these, or its salt.

The phthalamide derivative of the present invention or a salt thereof has structural features such as having an imidazopyridine ring group that a conventional compound does not have. By having such a structural feature, the compound of the present invention exhibits an excellent effect not only on Lepidoptera, but also on Thripidae, Coleoptera, Flies and Stink bugs. In particular, the compound of the present invention has an insecticidal effect against thrips, beetles, stink bugs, which is not disclosed or suggested in the prior art, and is not provided by conventional similar compounds. is there.
The above-mentioned compounds of the present invention are also effective against pests parasitic on pets such as dogs and cats or livestock such as cows and sheep.

In the definition of the general formula (1) of the phthalamide derivative of the present invention, the definitions described below apply to all claims. “Halo” means “halogen atom” and represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom,
“(C ₁ -C ₈ ) alkyl group” means, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group. , Tertiary pentyl group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, normal hexyl group, isohexyl group, 1,1,2-trimethylpropyl group, 3,3-dimethyl A linear or branched alkyl group having 1 to 8 carbon atoms such as a butyl group, a heptyl group, an octyl group, etc .;

“(C ₂ -C ₈ ) alkenyl group” means, for example, vinyl group, allyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 1-methyl-2- Linear or branched carbon atom number 2 such as propenyl group, 2-methyl-1-propenyl group, pentenyl group, 1-hexenyl group, 3,3-dimethyl-1-butenyl group, heptenyl group, octenyl group, etc. Represents 8 alkenyl groups,

“(C ₂ -C ₈ ) alkynyl group” means, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 3-methyl-1-propynyl Group, 2-methyl-3-propynyl group, pentynyl group, 1-hexynyl group, 3,3-dimethyl-1-butynyl group, heptynyl group, octynyl group, etc. An alkynyl group is shown.

“(C ₃ -C ₈ ) cycloalkyl group” means, for example, a cyclic alkyl group having 3 to 8 carbon atoms such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group and the like. Group,

“(C ₁ -C ₈ ) alkoxy group” means, for example, methoxy group, ethoxy group, normal propoxy group, isopropoxy group, normal butoxy group, secondary butoxy group, tertiary butoxy group, normal pentyloxy group, isopentyl. Oxy group, tertiary pentyloxy group, neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group, 1-methylbutyloxy group, normal hexyloxy group, isohexyloxy group, 1,1 , 2-trimethylpropyloxy group, heptyloxy group, octyloxy group and the like linear or branched alkoxy groups having 1 to 8 carbon atoms,

“(C ₁ -C ₈ ) alkylthio group” means, for example, methylthio group, ethylthio group, normal propylthio group, isopropylthio group, normal butylthio group, secondary butylthio group, tertiary butylthio group, normal pentylthio group. Group, isopentylthio group, tertiary pentylthio group, neopentylthio group, 2,3-dimethylpropylthio group, 1-ethylpropylthio group, 1-methylbutylthio group, normal hexylthio group, isohexylthio group , 1,1,2-trimethylpropylthio group, heptylthio group, octylthio group and the like linear or branched alkylthio groups having 1 to 8 carbon atoms,

“(C ₁ -C ₈ ) alkylsulfinyl group” means, for example, methylsulfinyl group, ethylsulfinyl group, normal propylsulfinyl group, isopropylsulfinyl group, normal butylsulfinyl group, secondary butylsulfinyl group, tertiary butylsulfinyl group, Normal pentylsulfinyl group, isopentylsulfinyl group, tertiary pentylsulfinyl group, neopentylsulfinyl group, 2,3-dimethylpropylsulfinyl group, 1-ethylpropylsulfinyl group, 1-methylbutylsulfinyl group, normalhexylsulfinyl group, iso Linear or branched carbon such as hexylsulfinyl group, 1,1,2-trimethylpropylsulfinyl group, heptylsulfinyl group, octylsulfinyl group An alkylsulfinyl group having 1 to 8 atoms;

“(C ₁ -C ₈ ) alkylsulfonyl group” means, for example, a methylsulfonyl group, an ethylsulfonyl group, a normalpropylsulfonyl group, an isopropylsulfonyl group, a normalbutylsulfonyl group, a secondary butylsulfonyl group, a tertiary butylsulfonyl group, Normal pentylsulfonyl group, isopentylsulfonyl group, tertiary pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1-ethylpropylsulfonyl group, 1-methylbutylsulfonyl group, normal hexylsulfonyl group, iso A linear or branched alkylsulfonyl group having 1 to 8 carbon atoms such as hexylsulfonyl group, 1,1,2-trimethylpropylsulfonyl group, heptylsulfonyl group, octylsulfonyl group and the like is shown. The

The above “(C ₁ -C ₈ ) alkyl group”, “(C ₂ -C ₈ ) alkenyl group”, “(C ₂ -C ₈ ) alkynyl group”, “(C ₃ -C ₈ ) cycloalkyl group”, “(C ₁ -C ₈ ) alkoxy group”, “(C ₂ -C ₈ ) alkynyloxy group”, “(C ₃ -C ₈ ) cycloalkyl group”, “(C ₁ -C ₈ ) alkoxy group” One or two or more halogen atoms may be substituted at substitutable positions. When two or more halogen atoms are substituted, the halogen atoms may be the same or different. “Halo (C ₁ -C ₈ ) alkyl”, “Halo (C ₂ -C ₈ ) alkenyl”, “Halo (C ₂ -C ₈ ) alkynyl”, “Halo (C ₃ -C ₈ )” “Cycloalkyl group”, “halo (C ₁ -C ₈ ) alkoxy group”, “halo (C ₁ -C ₈ ) alkylthio group”, “halo (C ₁ -C ₈ ) alkylsulfinyl group”, “halo (C ₁ -C ₈₎ alkylsulfonyl group "refers to a" halo _(C 3 -C ₈₎ cycloalkyl group ".

  The “aryl group” refers to an aromatic hydrocarbon group having 6 to 10 carbon atoms such as a phenyl group, a 1-naphthyl group, and a 2-naphthyl group.

In addition, expressions such as “(C ₁ -C ₈ )”, “(C ₂ -C ₈ )”, and “(C ₃ -C ₈ )” indicate the range of the number of carbon atoms of various substituents. Further, it is possible to show the definition of groups in which the substituent is linked, for example, "(C 1 _{-C 8)} alkoxy (C 1 _{-C 8)} alkyl group" for straight-chain or branched It indicates that the alkoxy group having 1 to 8 carbon atoms is bonded to a linear or branched alkyl group having 1 to 8 carbon atoms.

Examples of the “(C ₁ -C ₈ ) alkylene group” include a methylene group, an ethylene group, a propylene group, an isopropylene group, and a butylene group.

R ¹ and R ² are bonded to each other and contain one nitrogen atom, and further contain 1 to 2 identical or different heteroatoms selected from an oxygen atom, a nitrogen atom, and a sulfur atom. Preferable 5- to 8-membered nitrogen-containing heterocycles include pyrrolidine, piperidine, morpholine, thiomorpholine, piperazine and the like.

  “Heterocyclic group” and “heterocycle” are 5- or 6-membered monocyclic aromatics containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms in addition to carbon atoms as ring-constituting atoms. Aromatic heterocyclic group or 3- to 6-membered monocyclic non-aromatic heterocyclic group, and condensed heterocyclic group in which the monocyclic aromatic or non-aromatic heterocyclic ring is condensed with a benzene ring, or the monocyclic And a condensed heterocyclic group in which aromatic or non-aromatic heterocyclic rings are condensed with each other (the heterocyclic rings may be different).

  Examples of the `` aromatic heterocyclic group '' include, for example, furyl, thienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, triazinyl and the like Cyclic aromatic heterocyclic groups; quinolyl, isoquinolyl, quinazolyl, quinoxalyl, benzofuranyl, benzothienyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzimidazolyl, benzotriazolyl, indolyl, indazolyl, pyrrolopyrazinyl, imidazopyr Aromatic condensed heterocyclic groups such as dinyl, imidazopyrazinyl, pyrazolopyridinyl, pyrazolothienyl, pyrazolotriazinyl and the like can be mentioned.

  Examples of the “non-aromatic heterocyclic group” include oxiranyl, thiylyl, aziridinyl, oxetanyl, thietanyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, hexamethyleneiminyl, oxazolidinyl, thiazolidinyl, azolidinyl, oxazolidinyl, oxazolidinyl, Imidazolinyl, dioxolyl, dioxolanyl, dihydrooxadiazolyl, 2-oxo-1,3-oxazolidine-5-yl, pyranyl, tetrahydropyranyl, thiopyranyl, tetrahydrothiopyranyl, 1-oxidetetrahydrothiopyranyl, 1,1- Dioxide tetrahydrothiopyranyl, tetrahydrofuryl, dioxanyl, pyrazolidinyl, pyrazolinyl, tetrahydropyrimidinyl, dihydride Monocyclic non-aromatic heterocyclic groups such as triazolyl and tetrahydrotriazolyl; dihydroindolyl, dihydroisoindolyl, dihydrobenzofuranyl, dihydrobenzodioxinyl, dihydrobenzodioxepinyl, tetrahydrobenzofuranyl, Non-aromatic condensed heterocyclic groups such as chromenyl, dihydroquinolinyl, tetrahydroquinolinyl, dihydroisoquinolinyl, tetrahydroisoquinolinyl, dihydrophthalazinyl and the like can be mentioned.

Examples of the “heterocyclic group” include isoquinolinyl, tetrazolyl, quinolinyl, isoxazolyl, pyrimidinyl, pyrazinyl, pyridyl, pyrazolyl, benzimidazolyl, 2,3-dioxoisoindolyl, tetrahydrofuranyl, oxiranyl, thienyl, pyridazinyl and the like. It is done.
Examples of the salt of the phthalamide derivative represented by the general formula (1) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate, acetate, fumarate, maleate, and oxalate. Examples thereof include organic acid salts such as methanesulfonate, benzenesulfonate, and paratoluenesulfonate, and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and trimethylammonium.

  The phthalamide derivative represented by the general formula (1) and a salt thereof of the present invention may have one or more asymmetric centers in the structural formula, and two or more optical isomers and diastereomers may be present. The present invention includes all the optical isomers and a mixture in which they are contained in an arbitrary ratio. In addition, the phthalamide derivative represented by the general formula (1) of the present invention and a salt thereof may include two geometric isomers derived from a carbon-carbon or carbon-nitrogen double bond in the structural formula. However, the present invention encompasses all geometric isomers and mixtures containing them in any proportion.

In the phthalamide derivative represented by the general formula (1) and the salt thereof of the present invention, preferred embodiments are exemplified as follows:
X ¹ is
(a1) a halogen atom;
_{(a6) (C 1 ~C 8} ) alkylthio group;
(a8) a (C ₁ -C ₈ ) alkylsulfinyl group; or
(a10) a (C ₁ -C ₈ ) alkylsulfonyl group, and X ² is
(b1) is a hydrogen atom,
Y is
(c1) hydrogen atom;
(c2) a halogen atom;
(c3) a cyano group;
_{(c4) (C 1 ~C 8} ) alkyl group;
_{(c6) (C 1 ~C 8} ) alkoxy groups;
_{(c8) (C 1 ~C 8} ) alkylthio group; or
(c10) a (C ₁ -C ₈ ) alkylsulfinyl group,
W ² is,
(e1) hydrogen atom;
(e3) a cyano group;
_{(e6) (C 1 ~C 8} ) alkyl group;
_{(e10) (C 3 ~C 8} ) cycloalkyl group;
_{(e11) (C 3 ~C 8} ) cycloalkyl _(C 1 _{~C 8)} alkoxy groups;
_{(e12) (C 1 ~C 8} ) alkoxy groups;
_{(e13) (C 1 ~C 8} ) alkoxy _(C 1 _{~C 8)} alkyl group;
_{(e14) (C 1 ~C 8} ) haloalkyl group;
_{(e15) (C 1 ~C 8} ) haloalkoxy group;
_{(e18) (C 1 ~C 8} ) alkylthio group;
_{(e19) (C 1 ~C 8} ) alkylsulfinyl group;
_{(e20) (C 1 ~C 8} ) alkylsulfonyl group;
_{(e27) (C 1 ~C 8} ) alkoxycarbonyl group;
(e32) R ⁴ (R ⁵ ) N group (wherein R ⁴ and R ⁵ may be the same or different, a hydrogen atom, (C ₁ -C ₈ ) alkyl group, (C ₃ -C ₈ ) cycloalkyl) A group, (C ₁ -C ₈ ) alkylcarbonyl group, (C ₁ -C ₈ ) alkoxycarbonyl group, or (C ₁ -C ₈ ) alkoxy (C ₁ -C ₈ ) alkyl group);
(e33) R ⁴ (R ⁵ ) N carbonyl group (wherein R ⁴ and R ⁵ are the same as above);
(e34) R ⁴ (R ⁵ ) NCON (R ⁵ ) group (wherein R ⁴ and R ⁵ are the same as above);
(e36) an aryl group;
(e37) aryl group which may be the same or different, and (a) an aryl group having 1 to 5 substituents selected from a halogen atom and (f) (C ₁ -C ₈ ) haloalkyl group on the ring;
(e40) a heterocyclic group;
(e41) may be identical or different, a heterocyclic group having a _{(r) (C 1 -C 8} ) alkoxycarbonyl group, and (t) 1 to 5 substituents selected from phenylmethoxy carbonyl group on the ring; Or
(e42) a heterocyclic (C ₁ -C ₈ ) oxy group,
W ³ is,
(f1) hydrogen atom;
(f5) a cyano (C ₁ -C ₈ ) alkyl group;
_{(f6) (C 1 ~C 8} ) alkyl group;
_{(f7) (C 2 ~C 8} ) alkenyl group;
_{(f8) (C 2 ~C 8} ) alkynyl group;
_{(f10) (C 3 ~C 8} ) cycloalkyl group;
_{(f11) (C 3 ~C 8} ) cycloalkyl _(C 1 _{~C 8)} alkoxy groups;
_{(f13) (C 1 ~C 8} ) alkoxy _(C 1 _{~C 8)} alkyl group;
_{(f14) (C 1 ~C 8} ) haloalkyl group;
(f21) a (C ₁ -C ₈ ) alkylthio (C ₁ -C ₈ ) alkyl group;
(f22) a (C ₁ -C ₈ ) alkylsulfinyl (C ₁ -C ₈ ) alkyl group;
(f23) a (C ₁ -C ₈ ) alkylsulfonyl (C ₁ -C ₈ ) alkyl group;
_{(f27) (C 1 ~C 8} ) alkoxycarbonyl group;
_{(f29) (C 1 ~C 8} ) alkoxycarbonyl _(C 1 _{~C 8)} alkyl group;
_{(f30) (C 1 ~C 8} ) alkylcarbonyl group;
(f32) R ⁴ (R ⁵ ) N carbonyl group (wherein R ⁴ and R ⁵ are the same as above);
(f33) R ⁴ (R ⁵ ) N sulfonyl group (wherein R ⁴ and R ⁵ are the same as above);
(f38) a heterocyclic group;
(f40) a heterocyclic carbonyl group; or
(f42) a heterocyclic (C ₁ -C ₈ ) alkyl group,
W ⁴ , W ⁵ , W ⁶ , and W ⁷ may be the same or different,
(g1) a hydrogen atom; or
(g6) a (C ₁ -C ₈ ) haloalkyl group,
R ¹ is
_{(h1) (C 1 ~C 8} ) alkyl group;
_{(h4) (C 3 ~C 8} ) cycloalkyl group;
(h5) a cyano (C ₁ -C ₈ ) alkyl group;
(h7) hydroxy _(C 1 _{~C 8)} alkyl group;
(h8) (C ₁ -C ₈ ) alkoxy (C ₁ -C ₈ ) alkyl groups;
(h9) a (C ₁ -C ₈ ) alkylthio (C ₁ -C ₈ ) alkyl group;
(h10) a (C ₁ -C ₈ ) alkylsulfinyl (C ₁ -C ₈ ) alkyl group;
(h11) a (C ₁ -C ₈ ) alkylsulfonyl (C ₁ -C ₈ ) alkyl group;
(h12) aryl _(C 1 _{~C 8)} alkyl group; or
(h14) R ⁴ (R ⁵ ) NCO ₂ (C ₁ -C ₈ ) alkyl group (wherein R ⁴ and R ⁵ are the same as above),
R ² is
(i1) a hydrogen atom; or
(i2) is a (C ₁ -C ₈ ) alkyl group; or
(i5) R ¹ and R ² are bonded to each other and contain one nitrogen atom, and further contain 1-2 identical or different heteroatoms selected from an oxygen atom, a nitrogen atom, and a sulfur atom. Can form a good 5- to 8-membered saturated nitrogen-containing heterocycle,
R ³ is
(j1) a hydrogen atom; or
(j2) An embodiment in which it is a (C ₁ -C ₈ ) alkyl group.

The following embodiments are exemplified as particularly preferred embodiments.
X ¹ is
(a1) a halogen atom; or
(a10) a (C ₁ -C ₈ ) alkylsulfonyl group, and X ² is
(b1) is a hydrogen atom,
Y is
(c1) hydrogen atom;
(c2) a halogen atom; or
_{(c4) (C 1 ~C 8} ) alkyl group,
W ² is,
_{(e12) (C 1 ~C 8} ) alkoxy group; or
(e14) a (C ₁ -C ₈ ) haloalkyl group,
W ³ is,
(f1) hydrogen atom;
_{(f6) (C 1 ~C 8} ) alkyl group;
_{(f8) (C 2 ~C 8} ) alkynyl; or
(f14) a (C ₁ -C ₈ ) haloalkyl group,
W ⁴ , W ⁵ , W ⁶ , and W ⁷ may be the same or different,
(g1) a hydrogen atom; or
(g6) a (C ₁ -C ₈ ) haloalkyl group,
R ¹ is
(h9) a (C ₁ -C ₈ ) alkylthio (C ₁ -C ₈ ) alkyl group;
(h10) a (C ₁ -C ₈ ) alkylsulfinyl (C ₁ -C ₈ ) alkyl group; or
_{(h11) (C 1 ~C 8} ) alkylsulfonyl _(C 1 _{~C 8)} alkyl group,
R ² is
(i1) is a hydrogen atom,
R ³ is
(j1) An embodiment in which it is a hydrogen atom.
Moreover, the compound which has 1 or 2 or more of each substituent which the above-mentioned or the following preferable aspect or specific compound has is preferable.

（式中、Ｘ^１、Ｘ^２、Ｙ、Ｚ^１、Ｚ^２、Ｚ^３、Ａ、Ｑ、Ｒ^１、Ｒ^２、又はＲ^３は前記に同じ。Ｍはハロゲン原子、メチルスルホニルオキシ基、又はｐ−トルエンスルホニルオキシ基等の脱離基を示す。） Although the typical manufacturing method of the phthalamide derivative represented by General formula (1) of this invention below is shown, the manufacturing method of the phthalamide derivative of this invention is not limited to these.
Manufacturing method 1.

(Wherein X ¹ , X ² , Y, Z ¹ , Z ² , Z ³ , A, Q, R ¹ , R ² , or R ³ are the same as above. M is a halogen atom, a methylsulfonyloxy group, or A leaving group such as a p-toluenesulfonyloxy group is shown.)

  It is represented by the general formula (2-1) or (2-2) produced according to the method described in JP-A-11-240857, JP-A-2001-131141, or JP-A-2002-326989. Is reacted with an amine derivative represented by the general formula (3) or (4) in an inert solvent in the presence or absence of an acid or a base. 1) or a phthalamide derivative represented by (1-2) can be produced, and the phthalamide derivative represented by the general formula (1-1) or (1-2) is isolated or not isolated. The phthalamide derivative represented by the general formula (1) can be produced by reacting with the compound represented by the general formula (5) or (6) in an inert solvent in the presence of a base.

1-1. General formula (2-1) or general formula (2-2) → General formula (1-1) or general formula (1-2)
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, dichlorobenzene, fluorobenzene, chain or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, esters such as ethyl acetate, dimethylformamide, dimethylacetamide, etc. Inert solvents such as amides, acids such as acetic acid, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone and the like, and these inert solvents may be used alone or in combination of two or more. Can be used.

  Since this reaction is an equimolar reaction, each reactant may be used in an equimolar amount, but an amine represented by the general formula (3) or the general formula (4) can be used in excess. 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 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. Moreover, it is also possible to use for the next reaction process, without isolating from a reaction system.

1-2. General formula (1-1) or general formula (1-2) → General formula (1)
The inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of the reaction. Aromatic hydrocarbons, methyl tertiary butyl ether, diethyl ether, 1,2-dimethoxyethane, dioxane, tetrahydrofuran and other chain or cyclic ethers, ethyl acetate and other esters, dimethylformamide, dimethylacetamide and other amides, An inert solvent such as 1,3-dimethyl-2-imidazolidinone can be exemplified, and these inert solvents can be used alone or in admixture of two or more.

Examples of the base used in this reaction include organic bases such as triethylamine and pyridine, inorganic bases such as potassium carbonate, sodium bicarbonate, sodium carbonate and sodium hydroxide,
Examples include alkali metal hydrides such as lithium hydride, sodium hydride and potassium hydride, alkali metal alcoholates such as sodium methoxide, sodium ethoxide and potassium tertiary butoxide, butyl lithium and the like. The amount used may be appropriately selected from an equimolar to excess molar range with respect to the phthalamide derivative represented by the general formula (1-1) or (1-2).

  Since this reaction is an equimolar reaction, the compound represented by the general formula (5) or (6) may be used in an equimolar amount, but any of the reactants may be used in excess. The reaction temperature can be from room temperature to the reflux temperature of the inert solvent to be used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within 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 according to a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.

Moreover, the general formula (1), in the definition of ^{R 1} in (1-1) and _(1-2), compounds showing _(C 1 -C ₈₎ alkylthio _(C 1 -C ₈₎ alkyl groups, those skilled in the art Is usually carried out by oxidation with an oxidizing agent such as m-chloroperbenzoic acid or hydrogen peroxide, so that R ¹ is a (C ₁ -C ₈ ) alkylsulfinyl (C ₁ -C ₈ ) alkyl group, Alternatively, a compound showing a (C ₁ -C ₈ ) alkylsulfonyl (C ₁ -C ₈ ) alkyl group can be produced. Further, it oxidized similarly sulfur atoms present in X ^1, can be produced sulfoxy body, a sulfone.
Moreover, the amine derivative represented by General formula (4) can be manufactured in accordance with the method described in the international publication 2001-23350 pamphlet, for example.

  Next, a typical method for producing an intermediate aniline derivative according to the phthalamide derivative represented by the general formula (3) of the present invention will be shown, but the present invention is not limited thereto.

（式中、Ｙ、Ｚ^１、Ｚ^２、Ｚ^３、Ａ、Ｑ及びＭは前記と同じ。） Manufacturing method 2.

(In the formula, Y, Z ¹ , Z ² , Z ³ , A, Q and M are the same as described above.)

The nitrobenzene derivatives represented by the general formula (3-1) include, for example, a derivative represented by the general formula (3-2) and a derivative represented by the general formula (7) in an inert solvent in the presence of a base. The compound represented by the general formula (3-1) can be produced by reacting with.
The inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction. For example, chain or cyclic aliphatic hydrocarbons such as pentane, hexane, and cyclohexane; Chain or cyclic ethers such as ether, methyl tertiary butyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF), diethylene glycol dimethyl ether (DGM); halogens such as methylene chloride, chloroform, carbon tetrachloride Aromatic hydrocarbons such as benzene, toluene and xylene; Halogenated aromatic hydrocarbons such as chlorobenzene, fluorobenzene and dichlorobenzene; Acetone, methyl ethyl ketone (MEK), methyl-i Ketones such as propyl ketone and methyl isobutyl ketone (MIBK); nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate and butyl acetate; dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone Inert solvents of acid amides such as 1,3-dimethyl-2-imidazolidinone can be exemplified, and these inert solvents can be used alone or in admixture of two or more.

Bases that can be used in this reaction include alkali metal carbonates and bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide. Alkali metal such as alkali metal and alkaline earth metal hydroxide, alkali metal amide such as lithium amide, sodium amide, potassium amide, etc., hydride of alkali metal such as lithium hydride, sodium hydride, potassium hydride, etc. Alkali metal alcoholates such as sodium methoxide, sodium ethoxide, potassium tertiary butoxide, etc., triethylamine, 1,1,4,4-tetramethylethylenediamine (TMEDA), N, N-dimethylaniline, N, N-diethylaniline, Pyridine, 4-dimethyl An organic base such as minopyridine (DMAP), 1,4-diazabicyclo [2,2,2] octane (DABCO) and 1,8-diazabicyclo [5,4,0] undec-7-ene (DBU) it can.
The said usage-amount can be suitably selected in the range of 1 molar equivalent to 10 molar equivalent with respect to the compound represented by General formula (3-1).

In addition, a phase transfer catalyst can be used in this reaction, for example, tetramethylammonium bromide, tetrapropylammonium bromide, tetrabutylammonium bromide, tetrabutylammonium bissulfate, tetrabutylammonium iodide, trioctylmethylammonium chloride, benzyl Quaternary ions such as triethylammonium bromide, butylpyridinium bromide, heptylpyridinium bromide, benzyltriethylammonium chloride; crown ethers such as dibenzo-18-crown-6, dicyclohexyl-18-crown-6, 18-crown-6 [2.2.2] -cryptate, [2.1.1] -cryptate, [2.2.1] -cryptate, [2.2. B] -cryptate, [2O2O2S] -cryptate, [3.2.2] -cryptate and the like can be shown.
The usage-amount can be suitably selected in the range of 0.001 molar equivalent to 1 molar equivalent with respect to the compound represented by General Formula (3-2).

  Since this reaction is an equimolar reaction, each reactant may be used in an equimolar amount, but either of the derivatives represented by the general formula (3-2) or the general formula (7) may be used in excess. it can. 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 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. Moreover, it is also possible to use for the next reaction process, without isolating from a reaction system.

  Here, the compound of the general formula (3-2) is a known publication of Chem. Abstr. 58, 3444e (1963); Bull. Soc. Chim. Fr. (1934) 539-545; Chem. Res. Miniprint, 8 (1987), 2133-2139; Chem. Soc. B, (1967), 1154-1158; Chem. Soc. (1961), 221-222; Amer. Chem. Soc. 111, 1989, pages 5880-5886, and the like. Specific examples include 4-nitrobenzyl chloride (commercially available), 4-bromobenzyl chloride (commercially available), 2-chloro-4-nitrobenzyl chloride, 2-methyl-4-nitrobenzyl chloride, 2-methoxy-4-nitro. Benzyl chloride, 3-chloro-4-nitrobenzyl chloride, 3-methyl-4-nitrobenzyl chloride, 3-methoxy-4-nitrobenzyl chloride, methanesulfonic acid 4-nitrobenzyl ester, methanesulfonic acid 2-chloro-4 -Nitrobenzyl ester, methanesulfonic acid 2-methyl-4-nitrobenzyl ester, methanesulfonic acid 2-methoxy-4-nitrobenzyl ester, methanesulfonic acid 3-chloro-4-nitrobenzyl ester, methanesulfonic acid 3-methyl -4-Nitrobenz Ester, methanesulfonic acid 3-methoxy-4-nitrobenzyl ester, methanesulfonic acid 1- (3-chloro-4-nitro-phenyl) -ethyl ester, methanesulfonic acid 1- (3-methyl-4-nitro-phenyl) ) -Ethyl ester, methanesulfonic acid 1- (3-methoxy-4-nitro-phenyl) -ethyl ester, and the like.

  In addition, nitro-substituted benzoic acids and esters thereof used as a raw material for the derivative represented by the general formula (3-2) are described in, for example, Chem. Ber. 52, 1919, 1083; Bull. Soc. Chim. Fr. (1962), 2255-2261; Tetrahedron, (1985), 115-118; Chem. Pharm. Bull. 41, (1993), pages 894-906, etc., and can be produced by the method described in the document or a method analogous thereto.

The derivative represented by the general formula (3-1) obtained by the reaction is reduced according to the method described in, for example, New Experimental Chemistry Course 14 Oxidation and Reduction [II] (Maruzen Co., Ltd.). Thus, an aniline derivative represented by the general formula (3) can be produced.

  Next, typical production methods of the related condensed heterocyclic derivatives represented by the general formula Q of the present invention are shown, but the production method of the present invention is not limited thereto.

（式中Ｗ^２、Ｗ^４、Ｗ^５、Ｗ^６及びＷ^７は、前記に同じ。）
一般式Ｑ１´（Ｗ²＝ＣＦ_３、アルキル基等）で表される誘導体類は、３，４−ジアミノピリジンを特開２００１−１２２８３６号の方法に準じて製造した６−ヘプタフルオロイソプロピルピリジン−３，４−ジアミン(Ｑａ)をＪ．Ａｍ．Ｃｈｅｍ．Ｓｏｃ．，７５巻、（１９５３年）、１２９２頁に記載の方法に準じて、６−ヘプタフルオロイソプロピル−２−トリフルオロメチル−１Ｈ−イミダゾ[４，５−Ｃ]ピリジンを製造することができる。 Manufacturing method 3-1. Manufacturing method of Q1 '

(W ² , W ⁴ , W ⁵ , W ⁶ and W ⁷ are the same as above.)
Derivatives represented by the general formula Q1 ′ (W ² = CF _3, alkyl group, etc.) are 6-heptafluoroisopropylpyridines produced by producing 3,4-diaminopyridine according to the method of JP-A-2001-122836. 3,4-diamine (Qa) was prepared according to J. Am. Am. Chem. Soc. 75, (1953), page 1292, 6-heptafluoroisopropyl-2-trifluoromethyl-1H-imidazo [4,5-C] pyridine can be produced.

（式中、Ｗ^４、Ｗ^５、Ｗ^６及びＷ^７は、前記に同じ。）
一般式（Ｑ３−２）で表される誘導体類は、前記(Ｑａ)から、Ｊ．Ｈｅｔｅｒｏｃｙｃｌ．Ｃｈｅｍ．，２巻、（１９６５年）、４１頁に記載の方法に準じて、６−（ヘプタフルオロイソプロピル）-１Ｈ−イミダゾ[４，５−Ｃ]ピリジン−２−オンを製造することができる。 Manufacturing method 3-2. Manufacturing method of Q3-2

(W ⁴ , W ⁵ , W ⁶ and W ⁷ are the same as above.)
The derivatives represented by the general formula (Q3-2) are those described in (Ja. Heterocycl. Chem. 2, (1965), page 41, 6- (heptafluoroisopropyl) -1H-imidazo [4,5-C] pyridin-2-one can be produced.

（式中、Ｗ³、Ｗ^４、Ｗ^５、Ｗ^６、Ｗ^７及びＭは、前記に同じくし、Ｗはアルコキシカルボニル基等の保護基を示す。）
一般式（Ｑ３´、Ｑ４´）で表される誘導体類は、前記(Ｑ３−２)をアルコキシカルボニルハライド等と反応して、一般式（Ｑ４−１、Ｑ３−１）で表される誘導体類に変換し、その後Ｗ^３Ｍと反応し、次いで脱保護することにより１位又は３位がＷ³で置換された６−（ヘプタフルオロイソプロピル）-１Ｈ−イミダゾ[４，５−Ｃ]ピリジン−２−オン類（Ｑ３´、Ｑ４´）を製造することができる。 Manufacturing method 3-3. Manufacturing method of Q3 'and Q4'

(W ³ , W ⁴ , W ⁵ , W ⁶ , W ⁷ and M are the same as defined above, and W represents a protecting group such as an alkoxycarbonyl group.)
Derivatives represented by general formulas (Q3 ′, Q4 ′) are derivatives represented by general formulas (Q4-1, Q3-1) by reacting (Q3-2) with an alkoxycarbonyl halide or the like. 6- (heptafluoroisopropyl) -1H-imidazo [4,5-C] pyridine-, which is substituted with W ³ at the 1-position or 3-position by subsequent reaction with W ³ M, followed by deprotection 2-ones (Q3 ′, Q4 ′) can be produced.

Typical examples of the phthalamide derivative represented by the general formula (1) of the present invention are illustrated in Tables 1 to 5 and Tables 11 to 15, but the present invention is limited to these. It is not a thing.
In the table, “n-” represents normal, iso “i-” represents iso, “t-” represents tertiary, “c-” represents alicyclic hydrocarbon group, “Ph” represents phenyl group, “ * "Indicates enantiomer S form. The physical properties indicate melting point (° C.), refractive index n _D (measurement temperature; ° C.) or NMR.

The present invention also relates to an aniline derivative or a salt thereof as an intermediate of the phthalamide derivative of the present invention, and the intermediates are exemplified in Tables 6 to 9.

  The agricultural and horticultural insecticide containing the phthalamide derivative represented by the general formula (1) of the present invention or a salt thereof as an active ingredient is various agricultural and forestry, horticultural, and stored grains that harm paddy rice, fruit trees, vegetables, other crops, and flowering plants. It is suitable for pest control such as pests, sanitary pests, and nematodes.

Examples of the pests or nematodes include the following:
Lepidoptera (Lepidoptera) pests include, for example, Aura moth (Parasa consocia), red killer whale (Anomis mesogona), swallowtail (Papilio xuthus), azukiyamamushiga (Matsumuraeses azukivora), azuki nomeiga (Ostrinia scapulalis), optera a emptera White butterfly (Hyphantria cunea), Common squirrel (Ostrinia furnacalis), Common squirrel (Pseudaletia separata), Common squirrel (Tinea translucens), Common squirrel (Bactra furfurana), Common squirrel (Parnara guttata), Common squirrel Sesamia inferens, Brachmia triannulella, Monema flavescens, Nettle squirrels (Trichoplusia ni), Pleuroptya ruralis, Cystidia couaggaria, Hydra scorpion (Lampides bodes) Giant tobacco (Helicoverpa armigera), Oto Monchachidoko (Phalerodonta manleyi), Greater green moth (Eumeta japonica), Greater white butterfly (Pieris brassicae), Okakareha (Malacosoma neustria testacea), Persimmon moth (Stathmopoda masinissa), Persimmon moth (Cuphodes diospyrosella moth) Tetramoera schistaceana, yellowtail (Papilio machaon hippocrates), yellow bat (Endoclyta sinensis), guinea winged moth (Lyonetia prunifoliella), golden horned moth (Phyllonorycter ringoneella), crimma (Cydia) Eucoenogenes aestuosa), Grapeberry moss (Lobesia botrana), Black-tailed green moth (Latoia sinica), Black-faced red-eye moth (Euzophera batangensis), Phalonidia mesotypa, Spilosoma imparides Memaki (Olethreutes mori), Koiga (Tineola bisselliella), Bat moth (Endoclyta excrescens), Kokuga (Nemapogon granellus), Cosca shiba (Synanthedon hector), Kodlinga (Cydia pomonella), Plutella xylostella, medusa Borer (Sesamia calamistis), Sankameiga (Scirpophaga incertulas), Shibata toga (Pediasia teterrellus), Potato moth (Phthorimaea operculella), Orchard moth (Stauropus fagi persimilis), Eleuella tena pod Bat (Palpifer sexnotata), Spodoptera mauritia, Scirpophaga innotata, Xestia c-nigrum, Spodoptera depravata, Anella prunus (Ephestia ku) , Seguro Hachiko (Clostera anastomosis), soy bean looper (Pseudoplusia includens), soybean Sayamushiga (Matsumuraeses falcana), Tobacco moth (Helicoverpa assulta), Tamanaginuwawa (Autographa nigrisigna), Tamanayagaga (Agrotis ipsilon), Chadokuga Caloptilia theivora, Homona magnanima, Ephestia elutella, Eumeta minuscula, Clostera anachoreta, Heliothis maritima, Ariana this pill, Ariana this Busseola fusca), Dokuga (Euproctis subflava), Tobimon Oedasaku (Biston robustum), Tomato fruit worm (Heliothis zea),

Aedia leucomelas, Narosoideus flavidorsalis, Nasikenmon (Viminia rumicis), Bucculatrix pyrivorella, Grapholita molesta, Chori sect. Allium moth (Acrolepiopsis sapporensis), Plodia interpunctella, Hellula undalis, Sitotroga cerealella, Spodoptera litura, A kind of leaf moth (Eucosma aariana Scopelodes contractus), Orgyia thyellina, Fall army worm (Spodoptera frugiperda), Ostrinia zaguliaevi, Naranga aenescens, Phalaenopsis (Andraca bipunctata), Anthracia gal Acosmeryx castanea, Phyllocnistis toparcha, Grape's leaflet (Endopiza viteana), Grape's leafworm (Eupoecillia ambiguella), Velvet bean caterpillar (Anticarsia gemmatalis), Hosoba's large leaflet (Cnephasia) , Dendrolimus spectabilis, Leguminivora glycinivorella, Maruca testulalis, Matsumuraeses phaseoli, Caloptilia soyella, Citrus indigo, trella Green-bellied spruce (Archips fuscocupreanus), Acanthoplusia agnata, Bambalina sp., Carposina niponensis, Conogethes punctiferalis, Conogethes punctiferalis, Synanthed (Lyonetia cl erkella, Papilio helenus, Monk butterfly (Colias erate poliographus), Monarch butterfly (Phalera flavescens), White butterfly (Pieris rapae crucivora), White butterfly (Pieris rapae), etc. Acrolepiopsis suzukiella), European corn borer (Ostrinia nubilalis), Mamestra brassicae, Artemisia da Asaku (Ascotis selenaria), Artemisia clandestina (Phtheochroides clandestina), Hoshinoa adumbisana apple (Triaena intermedia), apple cockroach (Adoxophyes orana fasciata), apple cocci (Grapholita inopinata), apple white spider (Spilonota ocellana), apple white spider (Spilonota lechriaspis), apple clam (Illiberis pruni), apple Himesinkui ( Argyresthia conjugella, Caloptilia zachrysa, Archips breviplicanus, Cotton squirrel (Anomis flava), Cotton bug (Pectinophora gossypiella), Cotton moth (Notarcha derogata), Cotton moth Heia D virescens), and wateringa (Earias cupreoviridis),

  Examples of the insects of the order Hemiptera (Hymenoptera) include the red beetle (Nezara antennata), the red beetle (Stenotus rubrovittatus), the red beetle (Graphosoma rubrolineatum), the red beetle (Trigonotylus coelestialium), (Aeschynteles maculatus), red beetle (Creontiades pallidifer), red beetle (Dysdercus cingulatus), red beetle (Chrysomphalus ficus), red beetle (Aonidiella aurantii), grouse, Icerya purchasi, Ichya beetle (Piezodorus hybneri), Yonekamemushi (Lagynotomus elongatus), White-footed beetle (Thaia subrufa), Japanese black-knot beetle (Scotinophara lurida), Ibarahi abosaito Stink bugs (Stariodes iwasakii), Aspidiotus destructor, Dwarf beetle (Taylorilygus pallidulus), Myzus mumecola, Pseudaulacaspis prunicola, Pyuda sumi tho si Helico beetle (Anacanthocoris striicornis), giant beetle beetle (Ectometopterus micantulus), giant beetle beetle (Eysarcoris lewisi), beetle beetle (Molipteryx fuliginosa), giant beetle (Cicadella viridno scorpion) Scale insect (Saissetia oleae), white spotted whitefly (Trialeurodes vaporariorum),

Agriahana quercus, Amysia beetle (Lygus spp.), Euceraphis punctipennis, Andaspis kashicola, Coccus pseudomagnoliarum, rus C , Chestnut beetle (Galeatus spinifrons), Chrysanthemum beetle aphid (Macrosiphoniella sanborni), Spotted beetle (Aonidiella citrina), Kusagi beetle (Halyomorpha mista), Kusugumbai (Stephanitis fasciicarina), Aeti rio L , Trichoza quercicola, Uhlerites latius, Grapeleaf hopper (Erythroneura comes), Paromius exiguus, Duplaspidiotus claviger Nephotettix nigropictus, Black-headed beetle (Halticiellus insularis), Black-headed beetle (Perkinsiella saccharicida), Black-headed whale (Psylla malivorella), Anomeura mori oc Pseudaulacaspis pentagona), Pulvinaria kuwacola, Apolygus lucorum, Togo hemipterus, Toxoptera aurantii, Sac charcharcoc sac charc lucifuga), sugar beetle (Numata muiri), San Jose scale insect (COMSTOCKASPIS perniciosa), citrus snow scale (Unaspis citri), potato beetle aphid (Aulacorthum solani), white beetle (E ysarcoris ventralis, silver leaf whitefly (Bemisia argentifolii), white leafhopper (Cicadella spectra), white beetle (Aspidiotus hederae), red beetle bug (Liorhyssus hyalinus), calophya nigris, califya nigris Broad bean aphid (Megoura crassicauda), Japanese radish aphid (Brevicoryne brassicae), soybean aphid (Aphis glycines), Aedes spider leaf (Leptocorisa oratorius), Aedes num-conosa eu (Nephotettix virescens) tennuis), tobacco whiteflies (Bemisia tabaci), tea cane scales (Lecanium persicae), tea scales (Parlatoria theae), tea scales (Pseudaonidia paeoniae), chanomid Empoasca onukii, Chalauen stink bug (Plautia stali), Tulipa aphid (Dysaphis tulipae), Tulip beetle aphid (Macrosiphum euphorbiae), Stephanitis pyrioides, Black worm (Ceroplastes cer) ), Bluefin beetle (Apolygus spinolai), Blackleaf beetle (Nephotettix cincticeps), Blue beetle (Glaucias subpunctatus), Sugar beetle (Orthotylus flavosparsus), Corn aphid (Rhopalosiphum maidis), Corn beetle (Erius maidus) , Cimex lectularius, Psylla abieti, Nilaparvata lugens, Psylla tobirae,

Sea turtles (Eurydema rugosum), pears (Schizaphis piricola), psylla pyricola, psylla pyricola, Parlatoreopsis pyri, pears (Stephanitis nashi), pears (Dysmicoccus wistariae) p , Nasimaru aphids (Sappaphis piri), Falcon radish aphids (Lipaphis erysimi), Nephirames (Neotoxoptera formosana), Huskvilea aphids (Rhopalosophum nymphaeae), Barahi mussels (Edwardsianarosae), Haridi strabiss pi alni), Speusotettix subfusculus, Alnetoidia alneti, Sogatella panicicola, Adelphocoris lineolatus, Dysdercus poecil us), larvae (Parlatoria ziziphi), larvae (Uhlerites debile), larvae (Laodelphax striatellus), larvae (Eurydema pulchrum), larvae (Cletus trigonus), larvae (Coleus trigonus) (Empoasca sp.), Octopus scales (Coccus hesperidum), scallops (Pachybrachius luridus), physalis scales (Planococcus kraunhiae), stag beetle (Stenotus binotatus), scallops (Macrosteles fascifrons), spotted beetle (Dolycoris baccarum), spotted beetle beetle (Adelphocoris triannulatus), grape aphid (Viteus vitifolii), beetle beetle (Acanthocoris sordidus), beetle octo beetle beetle (Macr opes obnubilus), Cletus punctiger, Riptortus clavatus, potato picilido (Paratrioza cockerelli),

Aphrophora costalis, Lyca disponsi, Lys saundersi, Crisicoccus pini, Empoasca abietis, Acrotis phi , Markopram (Megacopta punctatissimum), Marsila hornworm (Eysarcoris guttiger), citrus scale insect (Lepidosaphes beckii), citrus leaf moth (Diaphorina citri), citrus red aphid (Toxoptera citricidus), citrus plank octo citri), citrus white beetle (Aleurocanthus spiniferus), citrus leafworm (Pseudococcus citriculus), citrus leafhopper (Zyginella citri), citrus leafhopper (Pulvinaria citricola), citrus (Coccus discrepans), Pseudaonidia duplex, Pulvinaria aurantii, Lecanium corni, Nezara viridula, Stenodema calcarhops, humpadi ), Wheat beetle aphids (Sitobion akebiae), barley beetle (Schizaphis graminum), barley beetle (Sorhoanus tritici), barley beetle aphid (Brachycaudus helichrysi), purple beetle (Carpocoris purpurepens) (Hyalopterus pruni), Aphis farinose yanagicola, Metasalis populi, Unaspis yanonensis, Mesohomotoma camphorae, Aphis spirae la), apple aphids (Aphis pomi), apple oyster scales (Lepidosaphes ulmi), apple killer whales (Psylla mali), apple black turtles (Heterocordylus flavipes), apple aphids (Myzus malisuctus), apple aphids (Aphidonuguis mali), apples Spotted leaf beetle (Orientus ishidai), apple vulture beetle (Ovatus malicolens), apple beetle (Eriosoma lanigerum), ruby beetle (Ceroplastes rubens), cotton aphid (Aphis gossypii),

  Coleoptera (Coleoptera) pests include, for example, Xystrocera globosa, Aedes aegypti (Paederus fuscipes), Auchangamuri (Eucetonia roelofsi), Azuki weevil (Callosobruchus chinensis), Arimodokisakifa Weevil (Hypera postica), Rice weevil (Echinocnemus squameus), Rice beetle (Oulema oryzae), Rice beetle (Oulema oryzae), Rice beetle (Donacia provosti), Rice weevil (tus) Ladybird (Epilachna varivestis), common beetle (Acanthoscelides obtectus), western corn root worm (Diabrotica virgifera virgifera), beetle weevil (Involvulus cupreus), cucumber beetle (Aulacophora femoralis), pea Bruchus pisorum, Epilachna vigintioctomaculata, Carpophilus dimidiatus, Cassida nebulosa, Luperomorpha tunebrosa, Phylolta his Beetle (Aeolesthes chrysothrix), Curculio sikkimensis, Carpophilus hemipterus, Oxycetonia jucunda, Cornroot worm (Diabrotica spp.), Selenium dendrum (S) ), Tribolium castaneum, Sitophilus oryzae, Palorus subdepressus, Melonlontha japonica, Anoplophora malasiaca, Neat-eaten pi Leptinotarsa decemlineata, Southern corn rootworm (Diabrotica undecimpunctata howardi), Sphenophorus venatus, Crioceris quatuordecimpunctata, Conotrachelus nenupor, diaconthal Phaedon brassicae), tobacco beetle (Lasioderma serricorne), Sitona japonicus, Adoretus tenuimaculatus, Tenebrio molitor, H. Chaetocnema concinna, Anomala cuprea, Heptophylla picea, Epilachna vigintioctopunctata, Northern corn rootworm (Diabrotica longicornis), Eucetoni a pilifera), bark beetles (Agriotes spp.), ground beetles (Attagenus unicolor japonicus), Japanese red leaf beetle (Pagria signata), Japanese common scallop (Anomala rufocuprea), Japanese red-footed beetle (Palorus ratzeburgii), lame ga , Anthrenus verbasci, Lyctus brunneus, Tribolium confusum, Medythia nigrobilineata, Xylotrechus pyrrhoder cris, E (Tomicus piniperda), pine-nosed beetle (Monochamus alternatus), bean scallop (Popillia japonica), bean scorpion (Epicauta gorhami), maize weevil (Sitophilus zeamais), peach beetle weevil (Rhynchies heros), riszo Caterpillar (C allosobruchus maculatus), apple beetle (Phyllobius armatus), apple beetle (Anthonomus pomorum), luri beetle (Linaeidea aenea), and cotton weevil (Anthonomus grandis),

  Diptera (Flyidae) pests include, for example, Culex pipiens pallens, Pepomya hyoscyami, Liriomyza huidobrensis, Musca domestica, Chlorops orae Hydrellia sasakii, Agromyza oryzae, Green-spotted fly (Hydrellia griseola), Green-fly (Hydrellia griseola), Green-spotted fly (Ophiomyia phaseoli), Drosophila suzuki Fly flies (Rhacochlaena japonica), Muscina stabulans, fruit fly (Megaselia spiracularis) and other species, Clogmia albipunctata, Tripula reina (Pip) ), China Spotted fly (Anopheles sinensis), Hylemya brassicae, Soybean fly (Asphondylia sp.), Seed fly (Delia platura), Onion fly (Delia antiqua), European sweetfly (Rhagoletis cerasi), Chikaienka (Culex pi) (Ceratitis capitata), Bradysia agrestis, sugar beetle fly (Pegomya cunicularia), tomato leaf fly (Liriomyza sativae), eggplant leaf fly (Liriomyza bryoniae), sand leaf fly (Chromatomyia horticola) (Culex quinquefasciatus), Aedes aegypti, Aedes albopictus, bean leaf fly (Liriomyza trifolii), tomato leaf fly (Liriomyza sativae), citrus fly fly (Dacus dorsalis), citrus moth Fly (Sitodiplosis mosellana), Mugikimoguribae (Meromuza nigriventris), Mexico fruit fly (Anastrepha ludens), and apple maggot (Rhagoletis pomonella),

  Examples of Hymenoptera (Hymenoptera) pests include, for example, Pristomyrmex pungens, Arbatidae, Monomorium pharaohnis, Pheidole noda, Athalia rosae, Crispy bee (Dryocosmus kuriphils), japonica), hornets, Athalia infumata, Arge pagana, Japanese bee (Athalia japonica), Acromyrmex spp., Firenant (Solenopsis spp.), Apple bee (Arge mali), Ruriari (Ochetellus glaber),

  Examples of the insects of the order Diptera (Homoptera) include, butterfly (Homorocoryphus lineosus), Kera (Gryllotalpa sp.), Coxago (Oxya hyla intricata), Coxenata (Oxya yezoensis), Tosama migratoria, Oonica yap (O), Himeksakiri (Homorocoryphus jezoensis), and Enema cricket (Teleogryllus emma),

  Examples of thrips pests include, for example, Selenothrips rubrocinctus; obscurus), Liothrips floridensis, Gladiolus thrips (Thrips simplex), Black thrips (Thrips nigropilosus), Black thrips (Heliothrips haemrrhos) Thrips (Leeuwenia pasanii), Shiimaruda Thrips (Litotetothrips pasaniae), Citrus Srips (Scirtothrips citri), Saddle Thrips (Haplothrips chinensis), Soybean Thrips (Mycterothrips glycines), Soybean Usui Thrips setosus, Black-throated Thrips (Scirtothrips dorsalis), Black-headed Thrips (Dendrothrips ienwai), Thripsrips niger, Thrips tabaci, Thrips tabaci, Thrips tabaci ), Thrips coloratus, Thrips coloratus, Thrips coloratus, Thrips coloratus, Thalis thrips Thrips (Frankliniella lilivora), and Lithrips vaneeckei,

  For example, mite moths such as Leptotrombidium akamushi, American dock ticks (Dermacentor variabilis), house dust mites (Ornithonyssus bacoti), mite mites (Demodex canis), mite mites (Rhipicephalus sanguineus), Tetranychus ludeni), Tetranychus truncatus, Japanese spider mite (Tetranychus viennensis), Kanzawa spider mite (Tetranychus kanzawai), Stag beetle mite (Cheyletus malaccensis), Tiganphago mite (Tyrophagus putrescente) Dermacentor taiwanicus, Acaphylla theavagrans, Polyphagotarsonemus latus, Tomato mite (Aculops lycopersici), Ornithonyssus sylvairum, Nite mite (ticranychusur) Shrimp mite (Eriophyes chibaensis), Scarcoptes scabiei, Scarlet mite (Haemaphysalis longicornis), Black-legged tick (Ixodes scapularis), Spinach mite (Tyrophagus similis), Mite (Cheyletus anonymus mite) moorei), southern spider mite (Brevipalpus phoenicis), blue spider mite (Dermatophagoides ptrenyssnus), mountain tick (Haemaphysalis japonica), mountain spider mite (Ixodes ovat mite) ), Apple spider mite (Panonychus ulmi), lone star tic (Amblyomma americanum), and spider (Dermanyssus gallinae),

  Examples of the termite pests include the termite termite (Reticulitermes miyatakei), the American ant termite (Incisitermes minor), the termite (Coptotermes formosanus), the termite (Hodotermopsis japonica), the termite termite (Reticulitermes us, eticulitermes us). ), Termites (Glyptotermes kushimensis), white termites (Coptotermes guangzhoensis), white termites (Neotermes koshunensis), white termites (Glyptotermes kodamai), sandy termites (Glymento termites ), Termites termites (Glyptotermes nakajimai), termites termites (Pericapritermes nitobei), and termites termites (Reticulitermes speratus),

  For example, cockroaches (Periplaneta fuliginosa), German cockroach (Blattella germanica), Great cockroach (Blatta orientalis), Greater cockroach (Periplaneta brunnea), Greater cockroach (Blattella lituricollis), Greater cockroach jap American cockroach (Periplaneta americana),

Examples of fleas include human fleas (Pulex irritans), cat fleas (Ctenocephalides felis), and chicken fleas (Ceratophyllus gallinae),

  Nematodes include, for example, strawberry nematode (Nothotylenchus acris), rice pheasant nematode (Aphelenchoides besseyi), red beetle nematode (Pratylenchus penetrans), red beetle nematode (Meloidogyne hapla), sweet potato nematode, genita Globodera rostochiensis), Javaloid nematode (Meloidogyne javanica), Soybean cyst nematode (Heterodera glycines), Southern nematode nematode (Pratylenchus coffeae), Pterylenchus neglectus, and Mikanne nematode (Tylus)

  Mollusks include, for example, Pomacea canaliculata, Achatina fulica, slug (Meghimatium bilineatum), Lehmannina valentiana, Limax flavus, and Acusta despecta si .

  In addition, the agricultural and horticultural insecticide of the present invention has a strong insecticidal effect against other tomato pests (Tuta absoluta).

  Examples of animal parasitic mites that are one of the control targets of the animal parasite control agent of the present invention include Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, and Kita tick (Haemaphysalis). flava), tick tick (Haemaphysalis campanulata), tick tick (Haemaphysalis concinna), tick tick (Haemaphysalis japonica), tuna tuna (Haemaphysalis kitaokai), tick (Haxophysalis ias), tick (Haemaphysalis japonica) Ticks such as ticks (Ixodes persulcatus), Amblyomma testudinarium, Haemaphysalis megaspinosa, Dermacentor reticulatus, and Dermacentor taiwanesis , Spider mites (Dermanyssus gallinae), avian mite (Ornithonyssus sylviarum), and avian mite (Ornithonyssus bursa), Eutrombicula wichmanni, red tsutsugamushi (Leptotrombidium akamushi), L (Leptotrombidium fuji), Leptotrombidium tosa, European tick (Neotrombicula autumnalis), American tsutsugamushi (Eutrombicula alfreddugesi), and tsutsugamushi (Helenicula miyagawai); Cheyletiella parasitivorax), and crayfish ticks (Cheyletiella blakei), rabbits, Psoroptes cuniculi, Chorioptes bovis, Otodectes cynotis), mite mites such as Sarcoptes scabiei, and catfish mite (Notoedres cati), and mite mites such as the dog mite (Demodex canis). Among them, the animal parasite control agent containing the compound of the present invention is effective for controlling ticks and the like.

  Examples of fleas that are other control targets of the animal parasite control agent of the present invention include, for example, ectoparasite worms belonging to the order of Siphonaptera, more specifically, human flea family (Pulicidae), and Nagano family ( Ceratephyllus) and the like. Examples of fleas belonging to the family flea family include, for example, dog fleas (Ctenocephalides canis), cat fleas (Ctenocephalides felis), human fleas (Pulex irritans), elephant flea (Echidnophaga gallinacea), keops rat flea (Xenopsylla cheopis), Leptopsylla segnis), European rat minnow (Nosopsyllus fasciatus), and Japanese rat minnow (Monopsyllus anisus). The animal parasite control agent containing the compound of the present invention is particularly effective for controlling fleas belonging to the family Flea, particularly dog fleas and cat fleas.

  The ectoparasites that are further controlled by the animal parasite control agent of the present invention include, for example, bovine lice (Haematopinus eurysternus), foal lice (Haematopinus asini), sheep lice (Dalmalinia ovis), bovine lice (Linognathus vituli), pig lice (Haematopinus) suis), white lice (Phthirus pubis), and head lice (Pediculus humanus capitis), as well as white lice such as dog lice, blood-sucking dipterous pests such as the cattle fly (Tabanus trigonus), water hawks, and clawed moths Is mentioned. The animal parasite control agent of the present invention is also effective against endoparasites, and examples of such endoparasites include pneumoniae, benthic, nodular worms, gastric parasites, roundworms, and filamentous worms. Nematodes, crustaceans such as Manson's crested worm, caudate tapeworm, crustacea, multi-headed crustacea, single crested worm, and multi-crusted worms, schistosoma japonicum, and liver Insects such as moths, and protozoa such as coccidium, malaria parasites, intestinal granulocysts, toxoplasmas, and cryptosporidiums.

  The agricultural and horticultural insecticide containing the phthalamide derivative represented by the general formula (1) of the present invention as an active ingredient is effective against the above-mentioned pests that damage paddy field crops, field crops, fruit trees, vegetables, other crops, and flower buds. It has a remarkable control effect, so that it is possible to raise seedlings, paddy fields, fields, fruit trees, vegetables, other crops, flower buds, etc. before or when the occurrence of pests is confirmed, according to the time when the occurrence of pests is expected. The desired effect of the agricultural and horticultural insecticide of the present invention can be obtained by treating the seeds, paddy water, stalks and leaves, or soil and other cultivation carriers. Among them, it is treated with seedling soil such as crops, flower buds, planting hole soil at the time of transplantation, plant origin, irrigation water, cultivated water in hydroponics, etc., and the present compound is absorbed from the root through or without soil. Application utilizing the so-called osmotic transfer property by making it a preferable form of use.

  Useful plants to which the agricultural and horticultural insecticide of the present invention can be used are not particularly limited. Red beans, broad beans, green beans, green beans, peanuts, etc.), fruit trees and fruits (apples, citrus fruits, pears, peaches, peaches, plums, cherry peaches, walnuts, chestnuts, almonds, bananas, etc.), leaves and fruit vegetables (cabbage, Tomatoes, spinach, broccoli, lettuce, onions, green onions, peppers, eggplants, strawberries, peppers, porridges, etc.), root vegetables (carrots, potatoes, sweet potatoes, sweet potatoes, daikon, turnips, lotus roots, burdock, garlics, etc.), crops for processing (Salmon, hemp, beet, hop, sugar cane, sugar beet, olive, rubber, coffee, tobacco, tea, etc.), cucumbers (pumpkin, cucumber, watermelon, mackerel) Wow, melon, etc.), pastures (orchard grass, sorghum, timothy, clover, alfalfa, etc.), turf (Korean turf, bentgrass, etc.), fragrance and other ornamental crops (lavender, rosemary, thyme, parsley, pepper, Ginger, etc.), flowers (flowers, roses, carnations, orchids, etc.), garden trees (ginkgo, sakura, aoki, etc.), forest trees (todomatsu, spruce, pines, hiba, cedar, firewood, eucalyptus, etc.) Plants can be mentioned.

The “plant” includes HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr and thifensulfuron methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, cetoxydim and the like. Plants to which resistance to herbicides such as acetyl CoA carboxylase inhibitors, bromoxynil, dicamba, 2,4-D, etc. are imparted by classical breeding methods or gene recombination techniques are also included.

Examples of “plants” that have been given tolerance by classical breeding methods include rapeseed, wheat, sunflower, and rice that are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazetapil. Already on sale. Similarly, there are soybeans that are resistant to sulfonylurea ALS-inhibiting herbicides such as thifensulfuron methyl by classical breeding methods, and are already sold under the trade name of STS soybeans. Similarly, SR corn and the like are examples of plants to which tolerance has been imparted to acetyl CoA carboxylase inhibitors such as trion oxime and aryloxyphenoxypropionic acid herbicides by classical breeding methods.
Plants to which tolerance to an acetyl-CoA carboxylase inhibitor has been imparted are Procedures of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci). USA) 87, 7175-7179 (1990). A mutant acetyl CoA carboxylase resistant to an acetyl CoA carboxylase inhibitor has been reported in Weed Science 53, 728-746 (2005). A plant resistant to an acetyl-CoA carboxylase inhibitor can be created by introducing a mutation into a plant acetyl-CoA carboxylase, which is introduced into a plant or imparting resistance, and further, chimeric plastic technology (GuraT. 1999. Base substitution mutation-introduced nucleic acid typified by RepairingtheGenome's SpellingMistakes. Science 285: 316-318.) Is introduced into plant cells to give plant acetyl C By introducing site-specific amino acid substitution mutations into the oA carboxylase gene, ALS gene, etc., plants resistant to acetyl CoA carboxylase inhibitors, ALS inhibitors, etc. can be produced. Of agricultural and horticultural insecticides.

  Furthermore, as toxins expressed in transgenic plants, insecticidal proteins derived from Bacillus cereus and Bacillus popirie; δ- such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C derived from Bacillus thuringiensis Endotoxins, insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; nematicidal insecticidal proteins; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectins; Agglutinin; protease inhibitors such as trypsin inhibitor, serine protease inhibitor, patatin, cystatin, papain inhibitor; lysine, corn-RIP, abrin, ruffin, saporin, bryodin, etc. Zome inactivating protein (RIP); steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, cholesterol oxidase; ecdysone inhibitor; HMG-CoA reductase; sodium channel, calcium channel inhibitor, etc. Ion channel inhibitor; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; glucanase and the like.

  Further, as toxins expressed in such a genetically modified plant, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab or Cry35Ab or other δ-endotoxin proteins, VIP1, VIP2, VIP3 or VIP3A etc. Also included are insecticidal protein hybrid toxins, partially defective toxins, and modified toxins. Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques. As a toxin lacking a part, Cry1Ab lacking a part of the amino acid sequence is known. In the modified toxin, one or more amino acids of the natural toxin are substituted.

  Examples of these toxins and recombinant plants capable of synthesizing these toxins are described in EP-A-0374753, WO93 / 07278, WO95 / 34656, EP-A-0427529, EP-A-451878, WO03 / 052073 and the like. Has been.

  Toxins contained in these recombinant plants particularly confer resistance to Coleoptera, Hemiptera pests, Diptera pests, Lepidoptera pests and nematodes. The agricultural and horticultural insecticides of the present invention can be used in combination or systematized with these techniques.

The insecticide for agricultural and horticultural use according to the present invention is used as it is to control various pests, or appropriately diluted with water or the like, or suspended in an amount effective for controlling the pests or nematodes. For pests and nematodes occurring in fruit trees, cereals, vegetables, etc., in addition to spraying on the foliage, seed immersion in seeds, seed dressing, calper treatment Etc. Seed treatment, soil all layer mixing, crop application, floor soil mixing, cell seedling treatment, planting hole treatment, plant root treatment, top dress, rice box treatment, water surface application, etc. It can also be absorbed and used. In addition, it can be used for nutrient solution in nutrient solution (hydroponics) cultivation, smoke, or trunk injection.
Furthermore, the agricultural and horticultural insecticide of the present invention may be used as it is, appropriately diluted with water or the like or suspended in an amount effective for pest control in a place where the occurrence of the pest is predicted. For example, in addition to spraying on stored grain pests, house pests, sanitary pests, forest pests, etc., they can also be used as application to house building materials, smoke, bait and the like.

Seed treatment methods include, for example, a method in which a liquid or solid preparation is diluted or undiluted and the seed is immersed in a liquid state to infiltrate the drug, a solid preparation or liquid preparation is mixed with the seed, Examples thereof include a method of treating and adhering to the surface of the seed, a method of coating the seed by mixing with an adhesive carrier such as resin and polymer, and a method of spraying around the seed simultaneously with planting.
The “seed” for performing the seed treatment means a plant body at the initial stage of cultivation used for the propagation of plants, for example, for seeds, bulbs, tubers, seed buds, stock buds, baskets, bulbs, or cuttings. Mention may be made of plants for vegetative propagation.
The “soil” or “cultivation carrier” of the plant when carrying out the method of use of the present invention refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited. However, any material that can grow plants may be used, and so-called soil, seedling mats, water, etc. may be used. Specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel material, high It may be a molecular substance, rock wool, glass wool, wood chip, bark or the like.

As a spraying method to crop foliage or stored grain pests, house pests, hygiene pests, forest pests, etc., dilute liquid preparations such as emulsions and flowables or solid preparations such as wettable powders or granular wettable powders with water as appropriate. , A method of spraying, a method of spraying powder, smoke or the like.
Examples of the application method to the soil include, for example, a method in which a liquid preparation is diluted or not diluted with water and applied to a plant stock or a seedling nursery, etc. A method of spraying to a nursery, etc., a method of spraying powder, wettable powder, granule wettable powder, granule, etc. before sowing or transplanting and mixing with the whole soil, a planting hole, making before planting or planting a plant body Examples thereof include a method of spraying powder, wettable powder, wettable powder, granule, etc. on the strip.

As a method for applying rice to a seedling box, the dosage form may vary depending on the time of application such as application at sowing, greening period, application at transplanting, etc. Apply by mold. It can also be applied by mixing with soil, and it can be mixed with soil and powder, granulated wettable powder or granules, for example, mixed with ground soil, mixed with soil covering, mixed with the entire soil. Simply, the soil and the various preparations may be applied alternately in layers.
As a method of application to paddy fields, solid preparations such as jumbo agents, packs, granules, granule wettable powders, and liquid preparations such as flowables and emulsions are usually sprayed on flooded paddy fields. In addition, at the time of rice planting, an appropriate formulation can be sprayed and injected into the soil as it is or mixed with fertilizer. In addition, by using a chemical solution such as emulsion or flowable as a source of water flowing into a paddy field such as a water mouth or an irrigation device, it can be applied in a labor-saving manner along with the supply of water.

In field crops, it can be treated to seeds or a cultivation carrier close to the plant body from sowing to raising seedling. In plants that are sown directly in a field, in addition to direct treatment on seeds, treatment on the plant source of the plant being cultivated is suitable. For example, a spray treatment using a granule or a irrigation treatment in a liquid of a drug diluted or not diluted with water can be performed. It is also a preferable treatment to mix the granules with the cultivation carrier before sowing and then sow.
As the seeding of the cultivated plant to be transplanted and the treatment of the seedling raising period, in addition to the direct treatment to the seed, the irrigation treatment of the liquid drug or the granule spraying treatment to the seedling nursery is preferred. In addition, it is also a preferable treatment that a granule is treated in a planting hole at the time of planting or is mixed with a cultivation carrier in the vicinity of the transplantation site.
The agricultural and horticultural insecticide of the present invention is generally used in a form convenient for use according to a conventional method for agricultural chemical preparations.
That is, the derivative represented by the general formula (1) of the present invention or a salt thereof is dissolved, separated, suspended by blending these in an appropriate inert carrier or in an appropriate ratio together with an auxiliary as necessary. Appropriate dosage forms such as suspensions, emulsions, liquids, wettable powders, wettable powders, granules, powders, tablets, packs, etc. can be used by turbidity, mixing, impregnation, adsorption or adhesion. It ’s fine.

  The composition (agricultural and horticultural insecticide or animal parasite control agent) of the present invention may contain, in addition to the active ingredient, an additive component usually used for an agrochemical formulation or an animal parasite control agent as necessary. Examples of the additive component include a carrier such as a solid carrier and a liquid carrier, a surfactant, a dispersant, a wetting agent, a binder, a tackifier, a thickener, a colorant, a spreading agent, a spreading agent, and an antifreezing agent. , Anti-caking agents, disintegrants, decomposition inhibitors and the like. In addition, you may use a preservative, a plant piece, etc. for an additional component as needed. These additive components may be used alone or in combination of two or more.

  Examples of the solid support include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, diatomaceous earth, and inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride. Synthetic silica, synthetic silicate, starch, cellulose, organic solid carriers such as plant powder (eg sawdust, coconut cob, tobacco stalk, etc.), plastic carriers such as polyethylene, polypropylene, polyvinylidene chloride, urea, An inorganic hollow body, a plastic hollow body, fumed silica (white carbon), etc. are mentioned. These may be used alone or in combination of two or more.

  Examples of the liquid carrier include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin. Alcohols, polyhydric alcohol compounds such as propylene glycol ether, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, tetrahydrofuran, etc. Ethers, normal paraffins, naphthenes, isoparaffins, kerosene, mineral oils and other aliphatic hydrocarbons, Aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, alkylnaphthalene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, dimethyl adipate, etc. Esters, lactones such as γ-butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, N-alkylpyrrolidinone, nitriles such as acetonitrile, sulfur compounds such as dimethylsulfoxide, soybean oil, rapeseed oil, Examples thereof include vegetable oils such as cottonseed oil and castor oil, and water. These may be used alone or in combination of two or more.

  Examples of surfactants used as dispersants and wetting agents include sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, Polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene dialkyl phenyl ether, polyoxyethylene alkyl phenyl ether formalin condensate, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene Block polymer, alkyl polyoxyethylene polypropylene block copolymer ether, polyoxyethylene Alkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene diol, polyoxyalkylene-added acetylene diol, polyoxyethylene ether type silicone, ester type Nonionic surfactants such as silicone, fluorosurfactant, polyoxyethylene castor oil, polyoxyethylene hydrogenated castor oil,

  Alkyl sulfate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl phenyl ether sulfate, polyoxyethylene styryl phenyl ether sulfate, alkyl benzene sulfonate, alkyl aryl sulfonate, lignin sulfonate, alkyl sulfo succinate , Naphthalene sulfonate, alkyl naphthalene sulfonate, salt of formalin condensate of naphthalene sulfonic acid, salt of formalin condensate of alkyl naphthalene sulfonic acid, fatty acid salt, polycarboxylate, polyacrylate, N-methyl- Anionic surfactants such as fatty acid sarcosinate, resin acid salt, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl phenyl ether phosphate,

Cationic surfactants such as alkylamine salts such as laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride, alkyldimethylbenzalkonium chloride,

Examples include amphoteric surfactants such as amino acid type or betaine type.
These surfactants may be used alone or in combination of two or more.

  Examples of the binder and tackifier include carboxymethyl cellulose and salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinyl pyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and an average molecular weight of 6000 to 20000. Polyethylene glycol, polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, phospholipid (eg, cephalin, lecithin, etc.) cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compound, cross-linked polyvinyl pyrrolidone, maleic acid and styrenes A polymer, a (meth) acrylic acid copolymer, a half ester of a polymer composed of a polyhydric alcohol and a dicarboxylic acid anhydride, a water-soluble salt of polystyrene sulfonic acid, Emissions, terpene, polyamide resins, polyacrylate, polyoxyethylene, wax, polyvinyl alkyl ethers, alkylphenol-formalin condensates, synthetic resin emulsions, and the like.

  Examples of the thickener include xanthan gum, guar gum, diyutane gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch derivative, water-soluble polymer such as polysaccharide, high-purity bentonite, fumed silica (fumed Inorganic fine powders such as silica and white carbon.

  Examples of the colorant include inorganic pigments such as iron oxide, titanium oxide and Prussian blue, organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes.

  Examples of the antifreezing agent include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.

  Examples of adjuvants for preventing caking and promoting disintegration include polysaccharides such as starch, alginic acid, mannose, and galactose, polyvinylpyrrolidone, fumed silica (white carbon), ester gum, petroleum resin, sodium tripolyphosphate, Sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylate copolymer, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene / isobutylene / maleic anhydride copolymer, starch / polyacrylonitrile graft copolymer A polymer etc. are mentioned.

  Examples of the decomposition inhibitor include desiccants such as zeolite, quicklime and magnesium oxide, antioxidants such as phenolic compounds, amine compounds, sulfur compounds and phosphoric acid compounds, and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. It is done.

Examples of the preservative include potassium sorbate, 1,2-benzothiazolin-3-one, and the like.
Furthermore, functional aids, 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 supplements as necessary Agents can also be used.

  The blending ratio of the active ingredient compound can be adjusted as necessary, and it can be used by appropriately selecting from a range of 0.01 to 90 parts by weight in 100 parts by weight of the agricultural and horticultural insecticide of the present invention. In the case of powder, granule, emulsion or wettable powder, 0.01 to 50 parts by weight (0.01 to 50% by weight based on the total weight of the agricultural and horticultural insecticide) is appropriate.

The amount of the pest control agent of the present invention, particularly agricultural and horticultural insecticides, is various factors such as purpose, target pests, crop growth status, pest occurrence tendency, weather, environmental conditions, dosage form, application method, application Although it varies depending on the location, application time, etc., the active ingredient compound may be appropriately selected from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg per 10 ares according to the purpose.
The pesticides of the present invention, particularly agricultural and horticultural insecticides, can be further controlled against other pests, insecticides for agro-horticultural use, acaricides, It can be used by mixing with nematodes, fungicides, biological pesticides, etc., and it 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,

3,5-xylyl methylcarbamate (XMC), Bacillus thuringienses aizawai, Bacillus thuringienses israelensis, Bacillus thuringienses japonensis, Bacillus thuringienses kurstaki, Bacillus thuringienses tenebrionis, Bacillus thuringienses produced crystalline protein toxin, BPMC, Bt toxin C chlorfenson), DCIP (dichlorodiisopropyl ether), DD (1, 3-dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O, O-diethyl phosphorothioate (DSP), O-ethyl O-4-nitrophenyl phenylphosphonothioate (EPN), tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, azinphos-methyl, acequinocyl, acetamiprid, acetoprole, acephate, actin ), Avermectin-B, amidoflumet, amitraz, alanycarb, Aldicarb, aldoxycarb, aldrin, alpha-endosulfan, alpha-cypermethrin, albendazole, allethrin, isazofos, Isamidofos, isamidofos, isoxathion, isofenphos, isoprocarb (MIPC), ivermectin, imidaclos, imidacloprid (imidac1oprid), prothromlin (indoxacarb), esfenvalerate, ethiofencarb, ethion, ethiprole, etoxazole, etofenprox, ethoprophos, etrimfos, etrimfos, emamectin em amectin), emamectin-benzoate, endosulfan, empenthrin, oxamyl, oxydemeton-methyl, oxydeprofos (ESP), oxibendazole ), Oxfendazole, potassium oleate (Potassium oleate), sodium oleate,

Cadusafos, cartap, carbary1, carbsulfan, carbofuran, gamma-cyhalothrin, xylylcarb, quinalphos, quinoprene ), Quinomethionat, cloethocarb, clothianidin, clofentezine, chromafenozide, chlorantraniliprole, chlorethoxyfos, chlordiformol Chlordane, chlorpyrifos, chlorpyrifos-methyl, chlorphenapyr, chlorfenson, chlorfenson, ch1orfenvinphos, chlorfluazuron, chlorbenz Rate (chlorobenzilate) , Chlorobenzoate, kelsen (dicofol), salithion, cyanophos (CYAP), diafenthiuron, diamidafos, cyantraniliprole, theta-shi Permethrin (theta-cypermethrin), dienochlor, cyenopyrafen (cyenopyrafen), dioxabenzophos (dioxaenolan), sigma-cypermethrin (sigma-cypermethrin), diclofenthion (Dichlofenthion: ECP) cycloprothrin, dichlorvos (DDVP), disulfoton, dinotefuran, cyhalothrin, cyphenothrin, cyfluthrin, diflubenzuron, diflubenzuron, difluvidin, cyflumetofen , Shiheke Cyhexatin, cypermethrin, dimethylvinphos, dimethoate, dimefluthrin, silafluofen, cyromazine, spinetram, spinosad, spinosad, spinosad Fenodi (spirodiclofen), spirotetramat (spirotetramat), spiromesifen (spiromesifen), sulfluramid (sulfluramid), sulprofos (sulprofos), sulfoxaflor (sulfaflor), zeta-cypermethrin (zeta-cypermethrin), diazinon (diazinon) , Tau-fluvalinate, dazomet,

Thiacloprid, thiamethoxam, thiodicarb, thiocyclam, thiosultap, thiosultap-sodium, thiosultap-sodium, thionazin, thiometon, deet, Dieldrin, tetrach1orvinphos, tetradifon, tetramethylfluthrin, tetramethrin, tebupirimfos, tebufenozide, tebufenpyrad, tebufenpyrad, tebufenpyrad , Teflubenzuron, demeton-S-methyl, temephos, deltamethrin, terbufos, tralopyril, tralomethrin, transfluthrin , Triaza Triazamate, triazuron, trichlamide, trichlorphon (DEP), triflumuron, tolfenpyrad, nared (nalp: BRP), nithiazine, nitenpyram, Novaluron, noviflumuron, hydroprene, vaniliprole, bamidothion, parathion, parathion-methyl, halfenprox, halofenozide ), Bistrifluron, bisultap, bisultap, hydramethylnon, hydroxy propyl starch, binapacryl, bifenazate, bifenthrin, pymetrozine, Pyraclorfos, pyra Luprolol, pyridafenthion, pyridaben, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, pirimicarb, pyrimidifen -methy1), pyrethrin (pyrethrins),

Fipronil (fiproni1), fenazaquin, fenamiphos, fenamiphos, bromopropylate, fenitrothion (MEP), phenoxycarb, fenoxycarb, phenothrin, phenothrin, fenocarb , Fensulfothion, fenthion (MPP), fenthoate (PAP), fenvalerate, fenpyroximate, fenpropathrin, fenbendazole, fosthiazate ), Formetanate, butathiofos, buprofezin, furathiocarb, prarethrin, fluacrypyrim, fluazinam, fluazuron, fluenesulfone fluensulfone, flucycloxuron, flucythrinate, fluvalinate, flupyrazofos, flufenerim, flufenoxuron, flufenzine, flufenprox (flufenzine) flufenoprox), fluproxyfen, flubrocythrinate, flubendiamide, flumethrin, flurimfen, prothiofos, protrifenbute, flonicamid (flonicamid), propaphos, propargite: BPPS, propenofos, profluthrin, propoxur: PHC, bromopropylate, beta-cyfluthrin, hexa Hexaflumuron, hexythiazok (hexythiazox), heptenophos, permethrin, benclothiaz, bendiocarb, bensu1tap, benzoximate, benfuracarb, phoxim, phosalone , Fosthiazate, fosthietan, phosphamidon, phosphocarb, phosmet (PMP), polynactins, formetanate, formothion, phorate,

Machine oil, malathion, milbemycin, milbemycin-A, milbemectin, mecarbam, mesulfenfos, methomyl, metaldehyde , Metaflumizone, metamidophos, metam-ammonium, metam-sodium, methiocarb, methidathion (DMTP), methylisothiocyanate, methylneothiocyanate Decaneamide (methylneodecanamide), methylparathion (methylparathion), methoxadiazone (metoxadiazone), methoxychlor (methoxychlor), methoxyphenozide (methoxyfenozide), methofluthrin (metofluthrin), methoprene (methoprene), metolcarb (metolcarb), melfluthrin (meperfluthrin) hos), monocrotophos, monosultap, lambda-cyhalothrin, ryanodine, lufenuron, resmethrin, lepimectin, rotenone, levamisole hydrochloride (levamisol), fenbutatin oxide, morantel tartarate, methyl bromide, tricyclohexyltin hydroxide (cyhexatin), lime nitrogen (Calcium cyanamide), lime sulfur compound (Calcium polysulfide) Agricultural and horticultural insecticides such as sulfur, nicotine-sulfate, acaricides, and nematicides.

  Examples of agricultural and horticultural fungicides used for the same purpose include aureofungin, azaconazole, azithiram, acipetacs, acibenzolar, and acibenzolar-S. -methyl), azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, allyl alcohol, aldimorph, amobam , Isotianil, isovaledione, isopyrazam, isoprothiolane, ipconazole, iprodione, iprovalicarb, iprobenfos, imazalil (imazalil) il), iminoctadine, iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole, uniconazole, uniconazole-P, ecromesol echlomezole, edifenphos, etaconazole, ethaboxam, etirimol, etem, ethoxyquin, etridiazole, enestroburin, epconazole ), Oxadixyl, oxycarboxin, copper-8-quinolinolate, oxytetracycline, copper-oxinate, oxpoconazole, oxpoconazole Zorufumaru salt (oxpoconazole-fumarate), oxolinic acid (oxolinic acid), octhilinone (octhilinone), Ofurase (ofurace), orysastrobin (orysastrobin),

Soil fungicides such as metam-sodium, kasugamycin, carbamorph, carpropamid, carbendazim, carboxin, carvone, quinazamid, quinacetor (Quinacetol), quinoxyfen, quinomethionate, captafol, captan, kiralaxyl, quinconazole, quintozene, guazatine, cufraneb ), Cuprobam, glyodin, griseofulvin, climbazole, cresol, kresoxim-methyl, clozolinate, clotrimazole, clobe Chlobenthiazone, chloraniformethan, chloranil, chlorquinox, chloropicrin, chlorfenazole, chlorodinitronaphthalene, chlorothalonil, chloronelon (Chloroneb), zarilamid, salicylanilide, cyazofamid, diethyl pyrocarbonate, dietofencarb, cyclafuramid, cyclodicet, diclozoline, ich Diclobutrazol, dichlofluanid, cycloheximide, diclomezine, dicloran, dichlorophen (di) chlorophen, dichlone, disulfiram, ditalimfos, dithianon, diniconazole, diniconazole-M, diniconazole-M, dinecap, dinocap, dinocton , Dinosulfon, dinoterbon, dinobuton, dinopenton, dipyrithione, diphenylamine, diphenoconazole, cyflufenamid, ditormetri (fluflutriamidi) cyproconazole), cyprodinil, cyprofuram, cypendazole, simeconazole, dimethirimol, dimethomorph, simoxanil cymoxanil), dimoxystrobin (dimoxystrobin), methyl bromide (methyl bromide), ziram (ziram), silthiofam (silthiofam),

Streptomycin, spiroxamine, sultropen, sedaxane, zoxamide, dazomet, thiadiazin, thiadinil, thiadifluor, thiabendazole Thioxymid, thiochlorfenphim, thiophanate, thiophanate-methyl, thiophanate, thicyofen, thioquinox, chinomethionat, thifluzamide, thiram, thiram Decafentin, tecnazene, tecloftalam, tecoram, tetraconazole, debacarb, dehydroacetic acid (dehydro) acetic acid, tebuconazole, tebufloquin, dodicin, dodine, dodecylbenzenesulfonic acid bisethylenediamine copper complex (II), (DBEDC), dodemorph, drazoxolon, Triadimenol, triadimefon, triazbutil, triazoxide, triamiphos, triarimol, trichlamide, tricyclazole, triticonazole , Tridemorph, tributyltin oxide, triflumizole, trifloxystrobin, triforine, tolylfluanid, tolulofluanid tolclofos-methyl), natamycin (natamycin), Nabamu (nabam), nitro data monkey isopropyl (nitrothal-isopropyl), nitrostyrene (nitrostyrene), nuarimol (nuarimol), nonylphenol sulfonate, copper (copper nonylphenol sulfonate),

Halacrinate, validamycin, valifenalate, harpin protein, bixafen, picoxystrobin, picobenzamide, bithionol, bitertanol ), Hydroxyisoxazole, hydroxyisoxazole-potassium, binapacryl, biphenyl, piperalin, hymexazol, pyraoxystrobin, pyracarboride (Pyracarbolid), pyraclostrobin, pyrazophos, pyrametostrobin, pyriophenone, pyridiinitril, pyrifenox ox), pyribencarb, pyrimethanil, pyroxychlor, pyroxyfur, pyroquilon, vinclozolin, famoxadone, fenapanil (fenapanil), fenone fenaminosulf, fenarimol, fenitropan, phenoxanil, ferimzone, ferbam, fentin, fenpiclonil, fenpyrazamine, fenbuconazole , Fenfuram, fenpropidin, fenpropimorph, fenhexamid, phthalide, buthiobate, butyl Butylamine, bupirimate, fuberidazole, blasticidin-S, furametpyr, furaxylyl, fluraxyl, fluacrypyrim, fluazinam, fluoxastrobin ( fluoxastrobin, fluotrimazole, fluopicolide, fluopyram, fluoroimide, furcarbanil, furxapyroxad, fluquinconazole, fluconazole , Fluconazole-cis, fludioxonil, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol , Furfural, furmecyclox, flumetover, furmorph, flumorph, proquinazid, prochloraz, procymidone, prothiocarb, prothioconazole , Propamocarb, propiconazole, propineb, furophanate, probenazole, bromuconazole,

  Hexachlorobutadiene, hexaconazole, hexylthiofos, bethoxazin, benalaxyl, benalaxyl-M, benodanil, benomyl, pefurazoate , Benquinox, penconazole, benzamorf, pencicuron, benzohydroxamic acid, bentaluron, benthiazole, benthiavalicarb- isopropyl), penthiopyrad, penflufen, boscalid, phosdiphen, fosetyl, fosetyl-aluminum, polyoxins, Polyoxorim, polycarbamate, folpet, formaldehyde, machine oil, maneb, mancozeb, mandipropamid, microzoline, microbutanyl ( myclobutanil, mildiomycin, milneb, mecarbinzid, metasulfocarb, metazoxolon, metam, metam-sodium, metalaxyl ), Metalaxyl-M, metiram, methyl isothiocyanate, mepthyldinocap, metconazole, metsulfovax, metfuroxam, metmino Strobin, metrafenone, mepanipyrim, mefenoxam, meptyldinocap, mepronil, mebenil, methyl iodide (iodomethane), benzazole, benz Inorganic bactericides such as benzalkonium chloride, basic copper chloride, basic copper sulfate, silver metal, sodium hypochlorote, Cupric hydroxide, wettable sulfur, calcium polysulfide, potassium hydrogen carbonate, sodium hydrogen carbonate, sulfur ), Copper sulfate anhydride, nickel dimethyldithiocarbamate, oxine copper A copper-based compound, zinc sulfate (zinc sulfate), copper pentahydrate (copper sulfate) sulfate, an agricultural and horticultural fungicide and the like can be exemplified.

Similarly, herbicides include, for example, 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,3,6-TBA, 2,4,5-T, 2 , 4,5-TB, 2,4-D, 2,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4 -CPA, 4-CPA (4-chlorophenoxyacetic acid), 4-CPB, 4-CPP, MCP, MCPA, MCPA-thioethyl, MCPB, MCPB, ioxynil, acronifen, azafenidin ), Acifluorfen, aziprotryne, azimsulfuron, asuram, acetochlor, atrazine, atraton, anisuron, anilofos ), Aviglycine, abscisic acid, amicarbazone, amidosulfuron, amitrole, amino acid Aropyrachlor (aminocyclopyrachlor), Aminopyralid (aminopyralid), Amibuzin (amibuzin), Amiprophos-methyl (amiprophos-methyl), Ametridione (ametridione), Ametrin (ametryn), Arakuroru (alachlor), Aridoklor (allidochlor), Alloxydim (alloxydim) , Alorac, isouron, isocarbamid, isoxachlortole, isoxapyrifop, isoxaflutole, isoxaflutole, isoxaben, isosyl , Isonoruron, isoproturon, isopropalin, isopolinate, isomethiozin, inabenfide, ipazine, ipfencarbazone, ip Rimidamam (iprymidam), imazaquin, imazapic, imazapyr, imazamethapyr, imazamethabenz, imazamethabenz-methyl, imazamoap, imazamoap, imazamoap , Imazosulfuron, indaziflam, indanofan, indolebutyric acid, uniconazole-P (uniconazole-P), eglinazine, esprocarb, ethametsulfuron, ethametsulfuron Ethametsulfuron-methyl, ethalfluralin, etiolate, ethichlozate ethyl, etidimuron, etinofen, ethephon, ethoxysulfur Chlorosulfuron, ethoxyfen, etnipromid, etofumesate, etobenzanid, epronaz, erbon, endothal, oxadiazon, oxadialyl ), Oxaziclomefone, oxasulfuron, oxapyrazon, oxyfluorfen, oryzalin, orthosulfamuron, orbencarb,

Cafenstrole, cambendichlor, carbasulam, carfentrazone, carfentrazone-ethyl, carbutilate, carbetamide, carboxazole (Carboxazole), quizalofop, quizalofop-P, quizalofop-ethyl, xylachlor, quinoclamine, quinonamid, quinclorac, quinclorac Quinmerac, cumyluron, cliodinate, glyphosate, glufosinate, glufosinate-P, credazine, clethodim, cloxyfonac , Krodinaho (Clodinafop), clodinafop-propargyl, clotoluron, clopyralid, cloproxydim, cloprop, clobromuron, clofop, clomazone , Chlomethoxyni, Chlomethoxyfen, Clomeprop, Chlorazifop, Chlorazine, Cloransulam, Chloranocryl, Chloramben, Cloransulam-methyl ), Chloridazon, chlorimuron, chlorimuron-ethyl, chlorsulfuron, chlorthal, chlorthiamid, chlortoluron (chlo) rtoluron), chlornitrofen, chlorfenac, chlorfenprop, chlorbufam, chlorflurazole, chlorflurenol, chlorprocarb, chlorprocarb Fam (chlorpropham), chlormequat, chloreturon, chloroxynil, chloroxuron, chloropon, saflufenacil, cyanazine, cyanatrin, dialate ), Diuron, diethamquat, dicamba, cycluron, cycloate, cyclooxydim, diclosulam, cyclosulfamulone muron), dichlorprop, dichlorprop-P, diclolobenil, diclofop, diclofop-methyl, dichlormate, dichloralurea, diquat (Diquat), cisanilide, disul, siduron, dithiopyr, dinitramine, cinidon-ethyl, dinosum, dinosam, cinosulfuron, dinoseb , Dinoterb, dinofenate, dinoprop, cyhalofop-butyl, diphenamid, difenoxuron, difenopenten, difenzoquat, difenzoquat cybutryne), Shipra Cyprazine, cyprazole, diflufenican, diflufenzopyr, dipropetryn, cypromid, cyperquat, gibberellin, simazine, simazine, dimexano), dimethachlor, dimedazone, dimidazon, dimethametryn, dimethenamid, dimethenamid, simetryn, simeton, dimepiperate, dimefuron, cinmeline, cinmeline

Swep, sulglycapin, sulcotrione, sulfallate, sulfentrazone, sulfosulfuron, sulfometuron, sulfometuron-methyl , Secbumeton, sethoxydim, sebuthylazine, terbacil, daimuron, dazomet, dalapon, thiazafluron, thiazopyr, thiazopyr, thiazopyr, thiazopyr , Thiencarbazone-methyl, thiocarbazil, tioclorim, thiobencarb, thidiazimin, thidiazuron, thifensulfuron, thicarbazone-methyl Thifensulfuron-methyl, desmedipham, desmetryn, tetrafluron, tenylchlor, tebutam, tebuthiuron, terbumeton, tepraxidim tepraloxydim), tefuryltrione, tembotrione, delachlor, terbacil, terbucarb, terbuchlor, terbuthylazine, terbutryntop, ram , Tralkoxydim, triaziflam, triasulfuron, tri-allate, trietazine, tricamba, triclopyr, tridif Tritriphane, tritac, tritosulfuron, triflusulfuron, triflusulfuron-methyl, trifluralin, trifloxysulfuron, tripropindan (Tripropindan), tribenuron-methyl, tribenuron, trifop, trifopsime, trimeturon, naptalam, naproanilide, napropamide, Nicosulfuron, nitralin, nitrofen, nitrofluorfen, nipyraclofen, neburon, norflurazon, noruron, barban, paclo Paclobutrazol, paraquat, parafluron, haloxydine, haloxyfop, haloxyfop-P, halooxyfop-methyl, halosafen, halos Halosulfuron, halosulfuron-methyl, picloram, picolinafen, bicyclopyrone, bispyribac, bispyribac-sodium, pydanon, Pinoxaden, bifenox, piperophos, hymexazol, pyraclonil, pyrasulfotole, pyrazoloxyfen, pyrazosulfuron, pyrazosulfuron Pyrazosulfuron-ethyl, pyrazolate, pyranaflus, pyraflufen-ethyl, pyriclor, pyridafol, pyrithiobac, pyrithiobac-sodium ), Pyridate, pyrifalid, pyributicarb, pyribenzoxim, pyrimisulfan, pyrimisulfuron, pyriminobac-methyl, pyroxasulfone ( pyroxasulfone), pyroxsulam,

Fenasulam, phenisopham, fenuron, fenoxasulfone, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, Phenothiol, fenoprop, phenobenzuron, fenthiaprop, fenteracol, fentrazamide, phenmedipham, phenmedipham -ethyl), butachlor, butafenacil, butamifos, buthiuron, buthidazole, butate, butylate, buturon, butenachlor, butroxydim, butroxydim, Butralin, butroxydim, flazasulfuron, flamprop, furyloxyfen, prynachlor, primisulfuron-methyl, fluazifop , Fluazifop-P, fluazifop-butyl, fluazolate, fluroxypyr, fluothiuron, fluometuron, fluoroglycofen, flurochloridone (Flurochloridone), fluorodifen, fluoronitrofen, fluoromidine, flucarbazone, flucarbazone-sodium, fluchloralin, flucetosulfuron ( flucetosulfuron, fluthiacet, fluthiacet-methyl, flupyrsulfuron, flufenacet, flufenican, flufenpyr, flupropacil, flupropacil (Flupropanate), flupoxam (flupoxam), flumioxazin (flumioxazin), full microrack (flumiclorac), full microrack pentyl (flumiclorac-pentyl), flumipropyn (flumipropyn), flumedin (flumezin), fluometuron (fluometuron), flumetsulam (flumetsu) ), Fluridone, flurtamone, fluroxypyr, pretilachlor, proxan, proglinazine, procyazine, prodiamine , Prosulfalin, prosulfuron, prosulfocarb, propaquizafop, propachlor, propazine, propanil, propyzamide, pro Propisochlor, prohydrojasmon, propyrisulfuron, propham, profluazol, proflularin, prohexadione-calcium, propoxycarbazone (Propoxycarbazone), propoxycarbazone sodium (propoxycarbazone-sodium), propoxydim (profoxydim), bromacil, brompyrazon, promethrin, prometon, bromoxynil, Lomofenoxim, bromobutide, bromobonil, florasulam,

Hexachloroacetone, hexazinone, petoxoxamid, benazolin, penoxsulam, pebulate, beflubutamid, vernolate, perfluidone, becarbazone ), Benzadox, benzipram, benzylaminopurine, benzthiazuron, benzfendizone, bensulide, bensulfuron-methyl, benzoylprop ( benzoylprop), benzobicyclon, benzofenap, benzofluor, benzofluor, bentazone, pentanochlor, benthiocarb, Pendimethalin, pentoxazone, benfluralin, benfuresate, fosamine, fomeamine, foramsulfuron, forchlorfenuron, forchlorfenuron, maleic hydrazide (maleic hydrazide), mecoprop (mecoprop), mecoprop-P (mecoprop-P), mezinoterb (medinoterb), mesosulfuron, mesosulfuron-methyl, mesotrione (mesotrione), mesoprazine (mesoprazine) methoprotryne, metazachlor, methazole, metazosulfuron, metabenzthiazuron, metamitron, metamifop, metam, metal prop Methalpropalin, Methiuron, Methiozolin, Methiobencarb, Methyldymron, Metoxuron, Metosulam, Metosulfuron, Metosulfuron methyl , Metflurazon, metobromuron, metobenzuron, metometon, metolachlor, metribuzin, mepiquat-chloride, mefenacet, mefenacet, mefenacet, mefenacet, mefenacet, mefenacet ), Monalide, monisouron, monuron, monochloroacetic acid, monolinuron, molinate, morfamquat, iodosulfur (Iodosulfuron), iodosulfuron-methyl-sodium, iodobonil, iodomethane, lactofen, linuron, rimsulfuron, lenacil, rhodetanyl (iodosulfuron) Examples include herbicides such as rhodethanil, calcium peroxide, and methyl bromide.

  Examples of biological pesticides include nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), insect poxvirus (EntomopoXI virus, EPV) ) And other 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. use Microbial pesticides, by using mixed such as biological pesticides 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, 14-methyl-1- Can be used in combination with pheromone such as octadecene

  Examples of the production of the compound of the present invention and examples of the preparation of the insecticide and the insecticidal effect of the present invention are shown below, but the present invention is not limited to the examples.

３，４−ジアミノピリジン５．０ｇを酢酸エチル４６ ｍＬ、水４６ ｍＬの混合溶媒に加え、ヘプタフルオロ−２−ヨ−ドプロパン１６．３ｇ、炭酸ナトリウム１４．６ｇ及び硫酸水素テトラブチルアンモニウム１．０ｇを順次加えた。５０℃の湯浴中で撹拌し、亜ジチオン酸ナトリウム８．０ｇを少量ずつ３０分かけて加えた。添加終了後、１時間撹拌した。有機層を分離後、水、飽和食塩水で順次洗浄し、無水硫酸マグネシウムで乾燥した。硫酸マグネシウムを濾別し、溶媒を減圧留去し、得られた残渣をシリカゲルカラムクロマトグラフィ−で精製することにより、６−ヘプタフルオロイソプロピルピリジン−３，４−ジアミン０．５４ｇ及び２−ヘプタフルオロイソプロピルピリジン−３，４−ジアミン４．０７ ｇを得た。 Reference Example 1-1 Production method of 1.6-heptafluoroisopropylpyridine-3,4-diamine and 2-heptafluoroisopropylpyridine-3,4-diamine

5.0 g of 3,4-diaminopyridine is added to a mixed solvent of 46 mL of ethyl acetate and 46 mL of water, 16.3 g of heptafluoro-2-iodopropane, 14.6 g of sodium carbonate, and 1.0 g of tetrabutylammonium hydrogen sulfate. Were added sequentially. The mixture was stirred in a 50 ° C. hot water bath, and 8.0 g of sodium dithionite was added in small portions over 30 minutes. After the addition was complete, the mixture was stirred for 1 hour. The organic layer was separated, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. Magnesium sulfate was filtered off, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain 0.54 g of 6-heptafluoroisopropylpyridine-3,4-diamine and 2-heptafluoroisopropyl. 4.07 g of pyridine-3,4-diamine was obtained.

参考例１−１で得られた６−ヘプタフルオロイソプロピルピリジン−３，４−ジアミン１．０ ｇをトリフルオロ酢酸１０ｍＬに溶解し、加熱還流下に１０時間反応を行った。反応終了後、過剰のトリフルオロ酢酸を減圧下に留去し、得られた残渣を酢酸エチル−ヘキサン混合溶媒で洗浄することにより、６−ヘプタフルオロイソプロピル−２−トリフルオロメチル−１Ｈ−イミダゾ［４，５−ｃ］ピリジン１．１ｇを得た。
物性：ｍ．ｐ．１９１−１９２℃ Reference Example 1-2. 6-Heptafluoroisopropyl-2-trifluoromethyl-1H-imidazo [4,5-c] pyridine production method

1.0 g of 6-heptafluoroisopropylpyridine-3,4-diamine obtained in Reference Example 1-1 was dissolved in 10 mL of trifluoroacetic acid, and reacted for 10 hours under reflux with heating. After completion of the reaction, excess trifluoroacetic acid was distilled off under reduced pressure, and the resulting residue was washed with a mixed solvent of ethyl acetate-hexane to give 6-heptafluoroisopropyl-2-trifluoromethyl-1H-imidazo [ 1.1 g of 4,5-c] pyridine was obtained.
Physical properties: m. p. 191-192 ° C

参考例１−２で得られた６−ヘプタフルオロイソプロピル−２−トリフルオロメチル−１Ｈ−イミダゾ［４，５−ｃ］ピリジン０．４６ｇをアセトニトリル１０ｍＬに溶解し、炭酸カリウム０．９０ｇ, ４−（ブロモメチル）−２−メチルニトロベンゼン０．３０ｇを加え加熱還流下に6時間反応を行った。反応終了後、水を加え酢酸エチルで抽出し、集めた有機層を飽和食塩水で洗浄後、無水硫酸マグネシウムで乾燥した。硫酸マグネシウムを濾別し、溶媒を減圧留去し、得られた残渣をシリカゲルカラムクロマトグラフィ−で精製することにより、３−（３−メチル−４−ニトロベンジル）−６−ヘプタフルオロイソプロピル−２−トリフルオロメチル−１Ｈ−イミダゾ［４，５−ｃ］ピリジン０．１６ｇと１−(３−メチル−４−ニトロベンジル)−６−ヘプタフルオロイソプロピル−２−トリフルオロメチル−１Ｈ−イミダゾ［４，５−ｃ］ピリジン０．３４ ｇを得た。
３−（３−メチル−４−ニトロベンジル）−６−ヘプタフルオロイソプロピル−２−トリフルオロメチル−１Ｈ−イミダゾ［４，５−ｃ］ピリジン
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３，ｐｐｍ）：２．６０（３Ｈ，ｓ），５．６７（２Ｈ，ｓ），７．１３（１Ｈ，ｄ），７．１８（１Ｈ，ｓ），７．９９（１Ｈ，ｄ），８．２６−８．２９（１Ｈ，ｍ），８．７９（１Ｈ，ｓ）
１−(３−メチル−４−ニトロベンジル)−６−ヘプタフルオロイソプロピル−２−トリフルオロメチル−１Ｈ−イミダゾ［４，５−ｃ］ピリジン
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３，ｐｐｍ）：２．５８（３Ｈ，ｓ），５．６４（２Ｈ，ｓ），７．０２（１Ｈ，ｄ），７．０８（１Ｈ，ｓ），７．６５−７．６８（１Ｈ，ｍ），７．９７（１Ｈ，ｄ），９．３５（１Ｈ，ｓ） Intermediate Preparation Examples 1-1.3- (3-Methyl-4-nitrobenzyl) -6-heptafluoroisopropyl-2-trifluoromethyl-1H-imidazo [4,5-c] pyridine and 1- (3 -Methyl-4-nitrobenzyl) -6-heptafluoroisopropyl-2-trifluoromethyl-1H-imidazo [4,5-c] pyridine

0.46 g of 6-heptafluoroisopropyl-2-trifluoromethyl-1H-imidazo [4,5-c] pyridine obtained in Reference Example 1-2 was dissolved in 10 mL of acetonitrile, and 0.90 g of potassium carbonate, 4- (Bromomethyl) -2-methylnitrobenzene (0.30 g) was added, and the reaction was carried out for 6 hours under reflux with heating. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate. The collected organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Magnesium sulfate is filtered off, the solvent is distilled off under reduced pressure, and the resulting residue is purified by silica gel column chromatography to give 3- (3-methyl-4-nitrobenzyl) -6-heptafluoroisopropyl-2- 0.16 g of trifluoromethyl-1H-imidazo [4,5-c] pyridine and 1- (3-methyl-4-nitrobenzyl) -6-heptafluoroisopropyl-2-trifluoromethyl-1H-imidazo [4 0.34 g of 5-c] pyridine was obtained.
3- (3-Methyl-4-nitrobenzyl) -6-heptafluoroisopropyl-2-trifluoromethyl-1H-imidazo [4,5-c] pyridine
¹ H-NMR (CDCl ₃ , ppm): 2.60 (3H, s), 5.67 (2H, s), 7.13 (1H, d), 7.18 (1H, s), 7.9 (1H, d), 8.26-8.29 (1H, m), 8.79 (1H, s)
1- (3-Methyl-4-nitrobenzyl) -6-heptafluoroisopropyl-2-trifluoromethyl-1H-imidazo [4,5-c] pyridine
¹ H-NMR (CDCl ₃ , ppm): 2.58 (3H, s), 5.64 (2H, s), 7.02 (1H, d), 7.08 (1H, s), 7.65 -7.68 (1H, m), 7.97 (1H, d), 9.35 (1H, s)

中間体製造実施例１−１で得られた３−（３−メチル−４−ニトロベンジル）−６−ヘプタフルオロイソプロピル−２−トリフルオロメチル−１Ｈ−イミダゾ［４，５−ｃ］ピリジン０．１６ ｇをエタノ−ル５ｍＬ、水５ｍＬに溶解し、塩化アンモニウム０．０９ｇ、鉄粉０．１０ｇを加え、室温で３時間撹拌した。反応終了後、セライトを用いて不溶物を除去した後、水を加え酢酸エチルで抽出し、集めた有機層を飽和食塩水で洗浄後、無水硫酸マグネシウムで乾燥した。硫酸マグネシウムを濾別し、溶媒を減圧留去し、２−メチル−４−［（６−ヘプタフルオロイソプロピル−２−トリフルオロメチル−１Ｈ−イミダゾ［４，５−ｃ］ピリジン−３−イル）メチル］アニリンの粗生成物０．１８ｇを得た。 Intermediate Production Example 1. Preparation of 2-methyl-4-[(6-heptafluoroisopropyl-2-trifluoromethyl-1H-imidazo [4,5-c] pyridin-3-yl) methyl] aniline (Compound No. 11-3)

Intermediate Preparation 3- (3-Methyl-4-nitrobenzyl) -6-heptafluoroisopropyl-2-trifluoromethyl-1H-imidazo [4,5-c] pyridine obtained in Example 1-1 16 g was dissolved in 5 mL of ethanol and 5 mL of water, 0.09 g of ammonium chloride and 0.10 g of iron powder were added, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, insolubles were removed using celite, water was added and the mixture was extracted with ethyl acetate. The collected organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Magnesium sulfate was filtered off, the solvent was distilled off under reduced pressure, and 2-methyl-4-[(6-heptafluoroisopropyl-2-trifluoromethyl-1H-imidazo [4,5-c] pyridin-3-yl). 0.18 g of a crude product of methyl] aniline was obtained.

中間体製造実施例１で得られた２−メチル−４−［（６−ヘプタフルオロイソプロピル−２−トリフルオロメチル−１Ｈ−イミダゾ［４，５−ｃ］ピリジン−３−イル）メチル］アニリン０．１８ ｇ及び（Ｓ）−４−クロロ−３−（１−メチル−１−メチルチオエチルイミノ）−３Ｈ−イソベンゾフラン−１−オンの粗生成物０．１０ｇをアセトニトリル５ｍＬに溶解し、トリフルオロ酢酸０．０１ｇを加え、室温で３時間撹拌した。反応終了後、減圧下に溶媒を留去し、得られた残渣をシリカゲルカラムクロマトグラフィ−で精製することにより、（Ｓ）−３−クロロ−Ｎ^１−｛２−メチル−４−［（６−ヘプタフルオロイソプロピル−２−トリフルオロメチル−３Ｈ−イミダゾ[４，５−ｃ]ピリジン−３−イル）メチル］フェニル｝−Ｎ^２−［１−（メチルチオ）プロパン−２−イル］フタルアミド０．１６ｇを得た。物性：ｍ．ｐ．１１３−１１８℃ Example 1. (S) -3-Chloro-N ^1- {2-methyl-4-[(6-heptafluoroisopropyl-2-trifluoromethyl-3H-imidazo [4,5-c] pyridin-3-yl) methyl] ^phenyl} -N 2 - preparation of [1- (methylthio) propan-2-yl] phthalamide (compound No. 1-77)

Intermediate Preparation 2-Methyl-4-[(6-heptafluoroisopropyl-2-trifluoromethyl-1H-imidazo [4,5-c] pyridin-3-yl) methyl] aniline obtained in Example 1 .18 g and 0.10 g of a crude product of (S) -4-chloro-3- (1-methyl-1-methylthioethylimino) -3H-isobenzofuran-1-one were dissolved in 5 mL of acetonitrile and trifluoro Acetic acid 0.01g was added and it stirred at room temperature for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain (S) -3-chloro-N ^1- {2-methyl-4-[(6- heptafluoro-isopropyl-2-trifluoromethyl -3H- imidazo [4,5-c] pyridin-3-yl) methyl] ^phenyl} -N 2 - [1- (methylthio) propan-2-yl] phthalamide 0.16g Got. Physical properties: m. p. 113-118 ° C

実施例１で得られた（Ｓ）−３−クロロ−Ｎ^１−｛２−メチル−４−［（６−ヘプタフルオロイソプロピル−２−トリフルオロメチル−１Ｈ−イミダゾ[４，５−ｃ]ピリジン−３−イル）メチル］フェニル｝−Ｎ^２−［１−（メチルチオ）プロパン−２−イル］フタルアミド０．１０ ｇをクロロホルム３ｍＬに溶解し、氷冷下、ｍ−クロロ過安息香酸（７０％）０．０３ｇを加え、室温で１時間撹拌した。反応終了後、チオ硫酸ナトリウム水溶液、飽和重曹水、飽和食塩水で順次洗浄し、無水硫酸マグネシウムで乾燥した。硫酸マグネシウムを濾別し、溶媒を減圧留去し、得られた残渣をシリカゲルカラムクロマトグラフィ−で精製することにより、（Ｓ）−３−クロロ−Ｎ^１−｛２−メチル−４−［（６−ヘプタフルオロイソプロピル−２−トリフルオロメチル−１Ｈ−イミダゾ[４，５−ｃ]ピリジン−３−イル）メチル］フェニル｝−Ｎ^２−［１−（メチルスルフィニル）プロパン−２−イル］フタルアミド０．１０ｇを得た。
物性：ｍ．ｐ．１２７−１２９ ℃ Example 2 (S) -3-Chloro-N ^1- {2-methyl-4-[(6-heptafluoroisopropyl-2-trifluoromethyl-3H-imidazo [4,5-c] pyridin-3-yl) methyl] Preparation of phenyl} -N ^2- [1- (methylsulfinyl) propan-2-yl] phthalamide (Compound No. 1-78)

(S) -3-Chloro-N ^1- {2-methyl-4-[(6-heptafluoroisopropyl-2-trifluoromethyl-1H-imidazo [4,5-c] pyridine obtained in Example 1 3-yl) methyl] ^phenyl} -N 2 - [1- a (methylthio) propan-2-yl] phthalamide 0.10 g was dissolved in chloroform 3 mL, under ice-cooling, m- chloroperbenzoic acid (70% ) 0.03 g was added and stirred at room temperature for 1 hour. After completion of the reaction, the mixture was washed successively with aqueous sodium thiosulfate solution, saturated aqueous sodium hydrogen carbonate, and saturated brine, and dried over anhydrous magnesium sulfate. Magnesium sulfate was filtered off, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain (S) -3-chloro-N ^1- {2-methyl-4-[(6 -Heptafluoroisopropyl-2-trifluoromethyl-1H-imidazo [4,5-c] pyridin-3-yl) methyl] phenyl} -N ^2- [1- (methylsulfinyl) propan-2-yl] phthalamide 0 .10 g was obtained.
Physical properties: m. p. 127-129 ° C

参考例１−１で得られた６−ヘプタフルオロイソプロピルピリジン−３，４−ジアミン１６．０ｇをテトラヒドロフラン８０ｍＬに溶解し、１，１’−カルボニルジイミダゾ−ル１２．６ｇを加え加熱還流下で３時間攪拌した。反応終了後、水を加え酢酸エチルで抽出し、集めた有機層を飽和食塩水で洗浄後、無水硫酸マグネシウムで乾燥した。硫酸マグネシウムを濾別し、溶媒を減圧留去し、得られた結晶を酢酸エチル−ヘキサン混合溶媒で洗浄することにより６−ヘプタフルオロイソプロピル−１Ｈ−イミダゾ［４，５−ｃ］ピリジン−２（３Ｈ）−オン１６．９ ｇを得た。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３，ｐｐｍ）：７．１２（１Ｈ，ｓ），７．７０（１Ｈ，ｓ） Reference Example 2-Production of 1.6-heptafluoroisopropyl-1H-imidazo [4,5-c] pyridin-2 (3H) -one

16.0 g of 6-heptafluoroisopropylpyridine-3,4-diamine obtained in Reference Example 1-1 was dissolved in 80 mL of tetrahydrofuran, 12.6 g of 1,1′-carbonyldiimidazole was added, and the mixture was heated under reflux. Stir for 3 hours. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate. The collected organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Magnesium sulfate was filtered off, the solvent was distilled off under reduced pressure, and the obtained crystals were washed with a mixed solvent of ethyl acetate-hexane to give 6-heptafluoroisopropyl-1H-imidazo [4,5-c] pyridine-2 ( 16.9 g of 3H) -one was obtained.
¹ H-NMR (CDCl ₃ , ppm): 7.12 (1H, s), 7.70 (1H, s)

参考例２−１で得られた６−ヘプタフルオロイソプロピル−１Ｈ−イミダゾ［４，５−ｃ］ピリジン−２（３Ｈ）−オン０．５２ｇをＮ，Ｎ−ジメチルアセトアミド４．０ｍＬに溶解し、水素化ナトリウム０．０６ｇを加え室温で１時間攪拌した。二炭酸ジ−ｔ−ブチルのＮ，Ｎ−ジメチルアセトアミド４．０ｍＬ溶液を氷浴下で滴下し、室温で２時間攪拌した。反応終了後、水を加え酢酸エチルで抽出し、集めた有機層を飽和食塩水で洗浄後、無水硫酸マグネシウムで乾燥した。硫酸マグネシウムを濾別し、溶媒を減圧留去し、得られた残渣をシリカゲルカラムクロマトグラフィ−で精製することによりｔ−ブチル ２−オキソ−６−ヘプタフルオロイソプロピル−−２，３−ジヒドロ−１Ｈ−イミダゾ［４，５−ｃ］ピリジン−１−カルボキシレ−ト０．１６ ｇとｔ−ブチル ２−オキソ−６−ヘプタフルオロイソプロピル−１Ｈ−イミダゾ［４，５−ｃ］ピリジン−３（２Ｈ）−カルボキシレ−ト０．１２ ｇを得た。
ｔ−ブチル ２−オキソ−６−ヘプタフルオロイソプロピル−２，３−ジヒドロ−１Ｈ−イミダゾ［４，５−ｃ］ピリジン−１−カルボキシレ−ト
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３，ｐｐｍ）：１．６３（９Ｈ，ｓ），７．０５（１Ｈ，ｓ），７．３９（１Ｈ，ｓ），８．１０（１Ｈ，ｓ）
ｔ−ブチル ２−オキソ−６−ヘプタフルオロイソプロピル−１Ｈ−イミダゾ［４，５−ｃ］ピリジン−３（２Ｈ）−カルボキシレ−ト
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３，ｐｐｍ）：１．７３（９Ｈ，ｓ），７．７６（１Ｈ，ｄ），８．９４（１Ｈ，ｓ），１１．０（１Ｈ，ｂｒｓ） Reference Example 2-2. t-butyl 2-oxo-6-heptafluoroisopropyl-2,3-dihydro-1H-imidazo [4,5-c] pyridine-1-carboxylate and t-butyl 2-oxo-6-heptafluoroisopropyl Preparation of -1H-imidazo [4,5-c] pyridine-3 (2H) -carboxylate

0.52 g of 6-heptafluoroisopropyl-1H-imidazo [4,5-c] pyridin-2 (3H) -one obtained in Reference Example 2-1 was dissolved in 4.0 mL of N, N-dimethylacetamide, Sodium hydride 0.06g was added and it stirred at room temperature for 1 hour. A 4.0 mL solution of di-t-butyl dicarbonate in N, N-dimethylacetamide was added dropwise in an ice bath, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate. The collected organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Magnesium sulfate was filtered off, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain t-butyl 2-oxo-6-heptafluoroisopropyl-2,3-dihydro-1H- Imidazo [4,5-c] pyridine-1-carboxylate 0.16 g and t-butyl 2-oxo-6-heptafluoroisopropyl-1H-imidazo [4,5-c] pyridine-3 (2H) -0.12 g of carboxylate was obtained.
t-butyl 2-oxo-6-heptafluoroisopropyl-2,3-dihydro-1H-imidazo [4,5-c] pyridine-1-carboxylate
¹ H-NMR (CDCl ₃ , ppm): 1.63 (9H, s), 7.05 (1H, s), 7.39 (1H, s), 8.10 (1H, s)
t-butyl 2-oxo-6-heptafluoroisopropyl-1H-imidazo [4,5-c] pyridine-3 (2H) -carboxylate
¹ H-NMR (CDCl ₃ , ppm): 1.73 (9H, s), 7.76 (1H, d), 8.94 (1H, s), 11.0 (1H, brs)

参考例２−２で得られたｔ−ブチル ２−オキソ−６−ヘプタフルオロイソプロピル−１Ｈ−イミダゾ［４，５−ｃ］ピリジン−３−カルボキシレ−ト０．１３ｇをアセトニトリル５ｍＬに溶解し、炭酸カリウム０．１３ｇを加え攪拌した。ヨ−ドメタン０．０５ｇのアセトニトリル１ｍＬ溶液を滴下し、加熱還流下６時間反応を行った。反応終了後、水を加え酢酸エチルで抽出し、集めた有機層を飽和食塩水で洗浄後、無水硫酸マグネシウムで乾燥した。硫酸マグネシウムを濾別し、溶媒を減圧留去し、得られた残渣をシリカゲルカラムクロマトグラフィ−で精製することにより、ｔ−ブチル １−メチル−２−オキソ−６−ヘプタフルオロイソプロピル−１Ｈ−イミダゾ［４，５−ｃ］ピリジン−３−カルボキシレ−ト０．１２ｇを得た。
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３，ｐｐｍ）：１．７０（９Ｈ，ｓ），３．４８（３Ｈ，ｓ），７．３５（１Ｈ，ｄ），９．０２（１Ｈ，ｓ） Reference Example 2-3 t-butyl 1-methyl-2-oxo-6-heptafluoroisopropyl-1H-imidazo [4,5-c] pyridine-3 (2H) -carboxylate

0.13 g of t-butyl 2-oxo-6-heptafluoroisopropyl-1H-imidazo [4,5-c] pyridine-3-carboxylate obtained in Reference Example 2-2 was dissolved in 5 mL of acetonitrile, Potassium carbonate 0.13g was added and stirred. A solution of 0.05 g of iodomethane in 1 mL of acetonitrile was added dropwise, and the reaction was carried out for 6 hours under reflux with heating. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate. The collected organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Magnesium sulfate was filtered off, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain t-butyl 1-methyl-2-oxo-6-heptafluoroisopropyl-1H-imidazo [ 0.15 g of 4,5-c] pyridine-3-carboxylate was obtained.
¹ H-NMR (CDCl ₃ , ppm): 1.70 (9H, s), 3.48 (3H, s), 7.35 (1H, d), 9.02 (1H, s)

実施例２−３で得られたｔ−ブチル １−メチル−２−オキソ−６−ヘプタフルオロイソプロピル−１Ｈ−イミダゾ［４，５−ｃ］ピリジン−３（２Ｈ）−カルボキシレ−ト０．１２ｇを４Ｎ塩酸（酢酸エチル溶液）１０ｍＬに溶解し、室温で２４時間攪拌した。反応終了後、溶媒を減圧留去し、得られた残渣をアセトニトリル５ｍＬに溶解し、炭酸カリウム０．１１ｇを加え攪拌した。４−（ブロモメチル）−２−メチルニトロベンゼン０．０８ ｇを加え加熱還流下３時間攪拌した。反応終了後、水を加え酢酸エチルで抽出し、集めた有機層を飽和食塩水で洗浄後、無水硫酸マグネシウムで乾燥した。硫酸マグネシウムを濾別し、溶媒を減圧留去し、得られた残渣をシリカゲルカラムクロマトグラフィ−で精製することにより、１−メチル−３−（３−メチル−４−ニトロベンジル）−６−ヘプタフルオロイソプロピル−１Ｈ−イミダゾ［４，５−ｃ］ピリジン−２（３Ｈ）−オン０．１２ ｇを得た。 Intermediate Preparation Example 2.1.1-Methyl-3- (3-methyl-4-nitrobenzyl) -6-heptafluoroisopropyl-1H-imidazo [4,5-c] pyridin-2 (3H) -one Manufacturing of

0.12 g of t-butyl 1-methyl-2-oxo-6-heptafluoroisopropyl-1H-imidazo [4,5-c] pyridine-3 (2H) -carboxylate obtained in Example 2-3 Was dissolved in 10 mL of 4N hydrochloric acid (ethyl acetate solution) and stirred at room temperature for 24 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resulting residue was dissolved in 5 mL of acetonitrile, and 0.11 g of potassium carbonate was added and stirred. 4- (Bromomethyl) -2-methylnitrobenzene (0.08 g) was added, and the mixture was stirred with heating under reflux for 3 hours. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate. The collected organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Magnesium sulfate is filtered off, the solvent is distilled off under reduced pressure, and the resulting residue is purified by silica gel column chromatography to give 1-methyl-3- (3-methyl-4-nitrobenzyl) -6-heptafluoro. 0.12 g of isopropyl-1H-imidazo [4,5-c] pyridin-2 (3H) -one was obtained.

実施例２−１で得られた１−メチル−３−（３−メチル−４−ニトロベンジル）−６−ヘプタフルオロイソプロピル−１Ｈ−イミダゾ［４，５−ｃ］ピリジン−２（３Ｈ）−オン０．１２ｇをエタノ−ル５ｍＬ、水５ｍＬに溶解し、塩化アンモニウム０．０７ｇ、鉄粉０．０７ｇを加え、室温で３時間撹拌した。反応終了後、セライトを用いて不溶物を除去した後、水を加え酢酸エチルで抽出し、集めた有機層を飽和食塩水で洗浄後、無水硫酸マグネシウムで乾燥した。硫酸マグネシウムを濾別し、溶媒を減圧留去し、３−（４−アミノ−３−メチルベンジル）−１−メチル−６−ヘプタフルオロイソプロピル−１Ｈ−イミダゾ［４，５−ｃ］ピリジン−２（３Ｈ）−オン（化合物番号１３−２）を０．１２ｇ得た。
^１Ｈ−ＮＭＲ（ＣＤＣｌ３，ｐｐｍ）：２．１２（３Ｈ，ｓ），３．４９（３Ｈ，ｓ），３．６３（２Ｈ，ｂｒｓ），４．９５（２Ｈ，ｓ），６．６０（１Ｈ，ｄ），７．０３−７．０９（２Ｈ，ｍ），７．２９（１Ｈ，ｄ），８．２５（１Ｈ，ｓ） Intermediate Preparation Example 2.3 Preparation of 3- (4-amino-3-methylbenzyl) -1-methyl-6-heptafluoroisopropyl-1H-imidazo [4,5-c] pyridin-2 (3H) -one

1-Methyl-3- (3-methyl-4-nitrobenzyl) -6-heptafluoroisopropyl-1H-imidazo [4,5-c] pyridin-2 (3H) -one obtained in Example 2-1 0.12 g was dissolved in 5 mL of ethanol and 5 mL of water, 0.07 g of ammonium chloride and 0.07 g of iron powder were added, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, insolubles were removed using celite, water was added and the mixture was extracted with ethyl acetate. The collected organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Magnesium sulfate was filtered off, the solvent was distilled off under reduced pressure, and 3- (4-amino-3-methylbenzyl) -1-methyl-6-heptafluoroisopropyl-1H-imidazo [4,5-c] pyridine-2. 0.13 g of (3H) -one (Compound No. 13-2) was obtained.
^{1 H-NMR (CDCl3, ppm} ): 2.12 (3H, s), 3.49 (3H, s), 3.63 (2H, brs), 4.95 (2H, s), 6.60 ( 1H, d), 7.03-7.09 (2H, m), 7.29 (1H, d), 8.25 (1H, s)

中間体製造実施例２で得られた３−（４−アミノ−３−メチルベンジル）−１−メチル−６−ヘプタフルオロイソプロピル−１Ｈ−イミダゾ［４，５−ｃ］ピリジン−２（３Ｈ）−オン０．１２ｇ及び（Ｓ）−４−クロロ−３−（１−メチル−１−メチルチオエチルイミノ）−３Ｈ−イソベンゾフラン−１−オン０．１１ｇをアセトニトリル５ｍＬに溶解し、トリフルオロ酢酸０．０１ｇを加え、室温で３時間撹拌した。反応終了後、減圧下に溶媒を留去し、得られた残渣をシリカゲルカラムクロマトグラフィ−で精製することにより、（Ｓ）−３−クロロ−Ｎ^１−｛２−メチル−４−［（１−メチル−２−オキソ−６−ヘプタフルオロイソプロピル−１Ｈ−イミダゾ[４，５−ｃ]ピリジン−３（２Ｈ）−イル）メチル］フェニル｝−Ｎ^２−［１−（メチルチオ）プロパン−２−イル］フタルアミド０．１６ｇを得た。物性：ｍ．ｐ．１２６−１３４ ℃ Example 3 (S)-3-chloro ^-N 1 - {2-methyl-4 - [(1-methyl-2-oxo-6-heptafluoroisopropyl -1H- imidazo [4,5-c] pyridine -3 (2H) - preparation of [1- (methylthio) propan-2-yl] phthalamide (compound No. 3-7) - yl) methyl] ^phenyl} -N 2

Intermediate Preparation 3- (4-Amino-3-methylbenzyl) -1-methyl-6-heptafluoroisopropyl-1H-imidazo [4,5-c] pyridine-2 (3H)-obtained in Example 2 0.12 g of ON and 0.11 g of (S) -4-chloro-3- (1-methyl-1-methylthioethylimino) -3H-isobenzofuran-1-one were dissolved in 5 mL of acetonitrile, and 0. 01 g was added and stirred at room temperature for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography - purified by, (S)-3-chloro ^-N 1 - {2-methyl-4 - [(1- methyl-1H-2-oxo-6-heptafluoroisopropyl imidazo [4,5-c] pyridine -3 (2H) - yl) methyl] ^phenyl} -N 2 - [1- (methylthio) propan-2-yl ] 0.16 g of phthalamide was obtained. Physical properties: m. p. 126-134 ° C

実施例３で得られた（Ｓ）−３−クロロ−Ｎ^１−｛２−メチル−４−［（１−メチル−２−オキソ−６−ヘプタフルオロイソプロピル−１Ｈ−イミダゾ[４，５−ｃ]ピリジン−３（２Ｈ）−イル）メチル］フェニル｝−Ｎ^２−［１−（メチルチオ）プロパン−２−イル］フタルアミド０．１２ｇをクロロホルム５ｍＬに溶解し、氷冷下、ｍ−クロロ過安息香酸（７０％）０．０５ｇを加え、室温で１時間撹拌した。反応終了後、チオ硫酸ナトリウム水溶液、飽和重曹水、飽和食塩水で順次洗浄し、無水硫酸マグネシウムで乾燥した。減圧下に溶媒を留去し、得られた残渣をシリカゲルカラムクロマトグラフィ−で精製することにより、（Ｓ）−３−クロロ−Ｎ^１−｛２−メチル−４−［（１−メチル−２−オキソ−６−ヘプタフルオロイソプロピル−１Ｈ−イミダゾ[４，５−ｃ]ピリジン−３（２Ｈ）−イル）メチル］フェニル｝−Ｎ^２−［１−（メチルスルフィニル）プロパン−２−イル］フタルアミド０．０８ｇ及び（Ｓ）−３−クロロ−Ｎ^１−｛２−メチル−４−［（１−メチル−２−オキソ−６−ヘプタフルオロイソプロピル−１Ｈ−イミダゾ[４，５−ｃ]ピリジン−３（２Ｈ）−イル）メチル］フェニル｝−Ｎ^２−［１−（メチルスルホニル）プロパン−２−イル］フタルアミド０．０２ｇを得た。
化合物番号３−８の物性：ｍ．ｐ．１３３−１４１ ℃
化合物番号３−９の物性：ｍ．ｐ．１３０−１３６ ℃ Example 4 (S)-3-chloro ^-N 1 - {2-methyl-4 - [(1-methyl-2-oxo-6-heptafluoroisopropyl -1H- imidazo [4,5-c] pyridine -3 (2H) -Yl) methyl] phenyl} -N ^2- [1- (methylsulfinyl) propan-2-yl] phthalamide (compound no. 3-8) and (S) -3-chloro-N ^1- {2-methyl-4 -[(1-Methyl-2-oxo-6-heptafluoroisopropyl-1H-imidazo [4,5-c] pyridin-3 (2H) -yl) methyl] phenyl} -N ^2- [1- (methylsulfonyl) ) Propan-2-yl] phthalamide (Compound No. 3-9)

Obtained in Example 3 (S)-3-chloro ^-N 1 - {2-methyl-4 - [(1-methyl-2-oxo-6-heptafluoroisopropyl -1H- imidazo [4,5-c ] pyridine -3 (2H) - yl) methyl] ^phenyl} -N 2 - [1- a (methylthio) propan-2-yl] phthalamide 0.12g was dissolved in chloroform 5 mL, under ice-cooling, m- chloroperbenzoic 0.05 g of acid (70%) was added and stirred at room temperature for 1 hour. After completion of the reaction, the mixture was washed successively with aqueous sodium thiosulfate solution, saturated aqueous sodium hydrogen carbonate, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography - purified by, (S)-3-chloro ^-N 1 - {2-methyl-4 - [(1-methyl-2- Oxo-6-heptafluoroisopropyl-1H-imidazo [4,5-c] pyridin-3 (2H) -yl) methyl] phenyl} -N ^2- [1- (methylsulfinyl) propan-2-yl] phthalamide 0 .08g and (S)-3-chloro ^-N 1 - {2-methyl -4 - [(-1H- 1- methyl-2-oxo-6-heptafluoroisopropyl imidazo [4,5-c] pyridine -3 0.02 g of (2H) -yl) methyl] phenyl} -N ^2- [1- (methylsulfonyl) propan-2-yl] phthalamide was obtained.
Physical properties of compound No. 3-8: m. p. 133-141 ° C
Physical properties of compound No. 3-9: m. p. 130-136 ° 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
Compound of the present invention 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts The above components are uniformly mixed and dissolved to prepare an emulsion.

Formulation Example 2
Compound of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above is mixed and ground uniformly to form a powder.

Formulation Example 3
Compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts lignin sulfonate 5 parts The above is uniformly mixed, kneaded with an appropriate amount of water, granulated and dried to give granules.

Formulation Example 4
Compound of the present invention 20 parts Kaolin, synthetic highly dispersed silicic acid 75 parts Polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 5 parts The above is uniformly mixed and ground to obtain a wettable powder.

Test Example 1
Test for insecticide test against Frankliniellaoccidentalis The kidney leaf fixed on the agar medium was inoculated with female adults of orange thrips and allowed to lay eggs for one day, and then the female adults were removed. Further, after 3 days, hatching larvae on the leaf pieces were counted, and then a chemical solution diluted with 500 ppm of a drug containing the compounds described in Tables 1 to 5 as an active ingredient was sprayed. The number of this species larvae surviving 4 days after the treatment was investigated, the mortality rate was calculated by the following formula, and the following criteria were used. Two consecutive systems.

Judgment criteria. A ... 100% death rate
B ... 99% to 90% death rate
C ... Death rate 89% -80%
D ... Death rate 79% -50%
E ... 49% to 0% death rate

As a result of the above test, compound numbers 1-77, 1-78, 1-183, 1-184, 1-185, 1-192, 1-193, 1-194, 1-195,
1-196, 1-28 (2-28), 1-30 (2-30), 1-33 (2-33), 1-155 (2-149), 1-222 (2-216), 1 -224 (2-218), 1-241 (2-235), 1-264 (2-258), 1-265 (2-259), 1-266 (2-260), 1-271 (2- 265), 1-276 (2-270), 1-277 (2-271), 1-282 (2-276), 1-283 (2-277), 1-284 (2-278), 1- 289 (2-283), 1-290 (2-284), 1-298 (2-292), 1-299 (2-293), 1-300 (2-294), 1-314 (2-308) ), 2-77, 2-78, 2-79, 2-83, 2-84, 2-85, 2-95, 2-96, 2-97, 2-177, 2-178, 2-179, 2-180, 2-181, 2-182, 2-186, 2-187, 2-188, 2-189, 2-190, 2-191, 2-309, 3-1, 3-2, 3- 3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-16, 3-17, 3-18, 3-61, 3-62, 3-64, 3-65, 3-88, 3-89, 3-90, 3-94, 3-95, 3-96, 3-97, 3-98, 3-99, 3-167, 3-168, 3- 169, 3-176, 3-177, 3-178, 3-182, 3-183, 3-188, 3-194, 3-195, 3-196, 4-1, 4-2, 4-3, 4-4, 4-5, 4-6, 4-7, 4-8, 4-11, 4-12, 4-16, 4-17, 4-18, 4-19, 4-20, 4- 21, 4-61, 4-62, 4-63, 4-64, 4-65, 4-70, 4-71, 4-72, 4-73, 4-74, 4-75, 4-79, 4-80, 4-81, 4-88, 4-89, 4-90, 4-94, 4-97, 4- 98, 4-99, 4-112, 4-113, 4-114, 4-167, 4-168, 4-169, 4-170, 4-171, 4-172, 4-176, 4-177, The compounds 4-178, 4-182, 4-183, 4-184, 4-188, 4-189, 4-192, 4-194, 4-196, and 4-199 are against citrus thrips The effect of A was shown at 500 ppm. In addition, 1-28 (2-28) shows the evaluation result in the mixture of compound numbers 1-28 and 2-28. same as below.

  On the other hand, as a comparative compound, the effect at 500 ppm of Compound No. 153 described in WO / 2005/095351 was E. From this, it became clear that this invention compound shows the special insecticidal effect with respect to thrips compared with a comparison compound.

Test Example 2 Insecticidal test against green planthopper ( Nilaparvatalugens ) Disperse the compounds listed in Tables 1 to 5 in water and dilute them in 500 ppm chemical solution, immerse rice seedlings (variety: Nipponbare) in the chemical solution for 30 seconds and air-dry them. Put in a glass test tube, inoculate 10 each of the 3 green planthoppers, cap them, and check the number of live and dead insects 8 days after the inoculation. The determination was made according to

As a result of the above test, 1-77, 1-78, 1-183, 1-184, 1-185, 1-192, 1-193, 1-194, 1-195, 1-196, 1-199, 1 -28 (2-28), 1-29 (2-29), 1-30 (2-30), 1-31 (2-31), 1-32 (2-32), 1-153 (2- 147), 1-154 (2-148), 1-155 (2-149), 1-222 (2-216), 1-223 (2-217), 1-224 (2-218), 1- 240 (2-234), 1-241 (2-235), 1-242 (2-236), 1-265 (2-259), 1-270 (2-264), 1-271 (2-265 ), 1-272 (2-266), 1-276 (2-270), 1-277 (2-271), 1-282 (2-276), 1-288 (2-282), 1-289 (2-283), 1-290 (2-284), 1-298 (2-292), 1-300 (2-294), 1-314 (2-308), 1-316 (2-310) , 2-77, 2-78, 2-79, 2-83, 2-84, 2-85, 2-95, 2-96, 2-97, 2-177, 2-178, 2-179, 2 -180, 2-181, 2-186, 2-187, 2-188, 2-188, 2-309, 3-1, 3-2, 3-3, 3-4, 3-5, 3-7, 3-8 3-16, 3-17, 3-61, 3-64, 3-88, 3-89, 3-90, 3-95, 3-97, 3-98, 3-99, 3-167, 3 -168, 3-169, 3-178, 3-189, 3-194, 3-195, 3-196, 4-1, 4-2, 4-5, 4-6, 4-7, 4-8 , 4-10, 4-11, 4-12, 4-16, 4-17, 4-18, 4-19, 4-20, 4-21, 4-61, 4-62, 4-63, 4 -70, 4-71, 4-72, 4-73, 4-74, 4-75, 4-79, 4-80, 4-81, 4-88, 4-89, 4-90, 4-94, 4-97, 4-98, 4-99, 4-112, 4-113, 4- 114, 4-167, 4-168, 4-169, 4-170, 4-171, 4-172, 4-176, 4-177, 4-178, 4-182, 4-183, 4-188, The compounds of 4-189, 4-190, 4-191, 4-192, 4-193, 4-194, 4-195, 4-196, 4-197, 4-198, and 4-199 are On the other hand, the effect of A was shown at 500 ppm.

Test Example 3
Control test against peach aphid ( Myzuspersicae ) Chinese cabbage aphid larvae were inoculated by planting Chinese cabbage in a plastic pot having a diameter of 8 cm and a height of 8 cm. On the next day, a drug (500 ppm) containing the compound shown in Tables 1 to 5 as an active ingredient is sprayed on the stems and leaves of potted Chinese cabbage, air-dried, and the pot is stored in a greenhouse. The number of parasites of peach aphid infesting each Chinese cabbage was investigated, the control value was calculated from the following formula, and the determination was made according to the following criteria.

Ta: Number of parasites before spraying in the treated zone T: Number of parasites after spraying in the treated zone Ca: Number of parasites before spraying in the untreated zone C: Criteria for determining the number of parasites after spraying in the untreated zone.

A ... Control value 100%
B ... Control value 99% ~ 90%
C ... Control value 89% -80%
D ... Control value 79% -50%
E ... Control value 0% ~ 49%

  As a result of the above test, compound numbers 1-77, 1-78, 1-183, 1-184, 1-185, 1-192, 1-193, 1-194, 1-195, 1-196, 1-197 , 1-199, 1-28 (2-28), 1-29 (2-29), 1-30 (2-30), 1-31 (2-31), 1-32 (2-32), 1-33 (2-33), 1-155 (2-149), 1-282 (2-276), 1-284 (2-278), 1-300 (2-294), 2-77, 2 -78, 2-83, 2-84, 2-85, 2-95, 2-96, 2-97, 2-177, 2-178, 2-179, 2-180, 2-181, 2-182 , 2-187, 2-188, 2-189, 2-190, 2-191, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3 -16, 3-17, 3-18, 3-61, 3-62, 3-64, 3-65, 3-88, 3-89, 3-90, 3-94, 3-95, 3-97 , 3-98, 3-99, 3-167, 3-168, 3-169, 3-167, 3-168, 3-169, 3-176, 3-195, 4-2, 4-5, 4 -6, 4-7, 4-8, 4-16, 4-17, 4-18, 4-19, 4-20, 4-21, 4-61, 4-62, 4-63, 4-64 , 4-65, 4-70, 4-71, 4-72, 4-73, 4-74, 4-75, 4-79, 4-80, 4-81, 4-88, 4-89, 4 -90, 4-94, 4-97, 4-98, 4-99, 4-112, 4-113, 4-114, 4-167, 4-168, 4-169, 4-170, 4-171 , 4-172, 4-176, 4-177, 4-178, 4-183, 4-189, 4-194, 4-195, and 4-196 are Showing the effect of A at 500ppm against the green peach aphid.

Test Example 4 Diamondback moth (Plutellaxylostella) were spawning were released adults of Plutella xylostella in the insecticidal test Chinese cabbage seedlings for an active ingredient a compound according to Chinese cabbage seedlings with a production under eggs two days after the release, in Table 1 - Table 5 The drug to be used was immersed in a chemical solution diluted to 50 ppm for about 30 seconds, air-dried and then left in a thermostatic chamber at 25 ° C. Six days after immersion in the chemical solution, the number of hatching insects was investigated, the death rate was calculated according to the following formula, and the determination was made according to the following criteria. 1 ward, 10 heads, 3 systems.

Judgment criteria. A ... 100% death rate
B ... 99% to 90% death rate
C ... Death rate 89% -80%
D ... Death rate 79% -50%
E ... 49% to 0% death rate

  As a result of the above test, compound numbers 1-77, 1-78, 1-183, 1-184, 1-185, 1-192, 1-193, 1-194, 1-195, 1-196, 1-197 , 1-199, 1-28 (2-28), 1-29 (2-29), 1-30 (2-30), 1-31 (2-31), 1-32 (2-32), 1-33 (2-33), 1-153 (2-147), 1-222 (2-216), 1-223 (2-217), 1-224 (2-218), 1-234 (2 -228), 1-235 (2-229), 1-236 (2-230), 1-240 (2-234), 1-241 (2-235), 1-242 (2-236), 1 -264 (2-258), 1-265 (2-259), 1-266 (2-260), 1-270 (2-264), 1-271 (2-265), 1-272 (2- 266), 1-276 (2-270), 1-277 (2-271), 1-282 (2-276), 1-283 (2-277), 1-284 (2-278), 1- 288 (2-282), 1-289 (2-283), 1-298 (2-292), 1-299 (2-293), 1-300 (2-294), 1-314 (2-308) ), 1-316 (2-310), 2-77, 2-78, 2-79, 2-83, 2-84, 2-85, 2-95, 2-96, 2-97, 2-177 , 2-178, 2-179, 2-180, 2-181, 2-182, 2-186, 2-187, 2-188, 2-189, 2-190, 2-191, 2-213, 2 -309, 3-1, 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-16, 3-17, 3-18 , 3-61, 3-62, 3-64, 3-65, 3-88, 3-89, 3-90, 3-94, 3-95, 3-96, 3-97, 3-98, 3 -99, 3-177, 3-178, 3-182, 3-18 3, 3-184, 3-188, 3-189, 3-194, 3-195, 3-196, 4-1, 4-2, 4-3, 4-4, 4-5, 4-6, 4-7, 4-8, 4-10, 4-11, 4-12, 4-16, 4-17, 4-18, 4-19, 4-20, 4-21, 4-61, 4- 62, 4-63, 4-64, 4-65, 4-70, 4-71, 4-72, 4-73, 4-74, 4-75, 4-79, 4-80, 4-81, 4-88, 4-89, 4-90, 4-94, 4-97, 4-98, 4-99, 4-112, 4-113, 4-114, 4-167, 4-168, 4- 169, 4-170, 4-171, 4-172, 4-176, 4-177, 4-178, 4-183, 4-184, 4-188, 4-189, 4-190, 4-191, The compounds of 4-194, 4-195, 4-196, 4-197, 5-1, 5-2, 5-3, 5-4, 5-5, and 5-6 are at 50 ppm with respect to diamondback moth. The effect of A was shown.

Claims (7)

General formula (1):

[Wherein X ¹ is
(a1) a halogen atom;
_{(a2) (C 1 ~C 8} ) alkyl group;
_{(a3) (C 1 ~C 8} ) haloalkyl group;
_{(a4) (C 1 ~C 8} ) alkoxy groups;
_{(a5) (C 1 ~C 8} ) haloalkoxy group;
_{(a6) (C 1 ~C 8} ) alkylthio group;
_{(a7) (C 1 ~C 8} ) haloalkylthio group;
(a8) a (C ₁ -C ₈ ) alkylsulfinyl group;
_{(a9) (C 1 ~C 8} ) haloalkylsulfinyl group;
_{(a10) (C 1 ~C 8} ) alkylsulfonyl group; or
(a11) represents a (C ₁ -C ₈ ) haloalkylsulfonyl group,
X ² is,
(b1) a hydrogen atom;
(b2) a halogen atom;
_{(b3) (C 1 ~C 8} ) alkyl group;
_{(b4) (C 1 ~C 8} ) haloalkyl group;
_{(b5) (C 1 ~C 8} ) alkoxy group; or
(b6) represents a (C ₁ -C ₈ ) haloalkoxy group,
Y is
(c1) hydrogen atom;
(c2) a halogen atom;
(c3) a cyano group;
_{(c4) (C 1 ~C 8} ) alkyl group;
_{(c5) (C 1 ~C 8} ) haloalkyl group;
_{(c6) (C 1 ~C 8} ) alkoxy groups;
_{(c7) (C 1 ~C 8} ) haloalkoxy group;
_{(c8) (C 1 ~C 8} ) alkylthio group;
_{(c9) (C 1 ~C 8} ) haloalkylthio group;
_{(c10) (C 1 ~C 8} ) alkylsulfinyl group;
_{(c11) (C 1 ~C 8} ) haloalkylsulfinyl groups;,
_{(c12) (C 1 ~C 8} ) alkylsulfonyl group; or
(c13) represents a (C ₁ -C ₈ ) haloalkylsulfonyl group,
Y ¹ is
(d1) a halogen atom;
(d2) a (C ₁ -C ₈ ) alkyl group;
_{(d3) (C 1 -C 8} ) haloalkyl group;
_{(d4) (C 1 -C 8} ) alkoxy group; or
(d5) represents a (C ₁ -C ₈ ) haloalkoxy group,
Z ¹ , Z ² , and Z ³ may be the same or different, and are a nitrogen atom, CH, C—Y ¹ , or C—AQ (where C—AQ is Z ¹ , Z ² , Or only one that binds to any one of Z ³ ).
A represents a linear or branched (C ₁ -C ₈ ) alkylene group,
Q represents a fused heterocyclic group selected from the group listed below.

“In the formula, the part marked with.
Where W ² is
(e1) hydrogen atom;
(e2) a halogen atom;
(e3) a cyano group;
(e4) Formyl group
(e5) a cyano (C ₁ -C ₈ ) alkyl group;
_{(e6) (C 1 ~C 8} ) alkyl group;
_{(e7) (C 2 ~C 8} ) alkenyl group;
_{(e8) (C 2 ~C 8} ) alkynyl group;
_{(e9) (C 2 ~C 8} ) haloalkenyl group;
_{(e10) (C 3 ~C 8} ) cycloalkyl group;
_{(e11) (C 3 ~C 8} ) cycloalkyl _(C 1 _{~C 8)} alkoxy groups;
_{(e12) (C 1 ~C 8} ) alkoxy groups;
_{(e13) (C 1 ~C 8} ) alkoxy _(C 1 _{~C 8)} alkyl group;
_{(e14) (C 1 ~C 8} ) haloalkyl group;
_{(e15) (C 1 ~C 8} ) haloalkoxy group;
_{(e16) (C 3 ~C 8} ) halocycloalkyl group;
_{(e17) (C 3 ~C 8} ) halocycloalkyl _(C 1 _{~C 8)} alkyl group;
_{(e18) (C 1 ~C 8} ) alkylthio group;
_{(e19) (C 1 ~C 8} ) alkylsulfinyl group;
_{(e20) (C 1 ~C 8} ) alkylsulfonyl group;
(e21) a (C ₁ -C ₈ ) alkylthio (C ₁ -C ₈ ) alkyl group;
(e22) a (C ₁ -C ₈ ) alkylsulfinyl (C ₁ -C ₈ ) alkyl group;
(e23) a (C ₁ -C ₈ ) alkylsulfonyl (C ₁ -C ₈ ) alkyl group;
_{(e24) (C 1 ~C 8} ) haloalkylthio group;
_{(e25) (C 1 ~C 8} ) haloalkylsulfinyl group;
_{(e26) (C 1 ~C 8} ) haloalkylsulfonyl groups;
_{(e27) (C 1 ~C 8} ) alkoxycarbonyl group;
_{(e28) (C 2 ~C 8} ) alkenyloxycarbonyl group;
(e29) a (C ₁ -C ₈ ) alkoxycarbonyl (C ₁ -C ₈ ) alkyl group;
_{(e30) (C 1 ~C 8} ) alkylcarbonyl group;
_{(e31) (C 3 ~C 8} ) cycloalkyl group;
(e32) R ⁴ (R ⁵ ) N group (wherein R ⁴ and R ⁵ may be the same or different, a hydrogen atom, (C ₁ -C ₈ ) alkyl group, (C ₃ -C ₈ ) cycloalkyl) _{group, (C} 2 -C _{8) alkenyl, (C} 2 -C _{8) alkynyl, (C} 3 -C ₈₎ cycloalkyl _(C 1 -C ₈₎ alkyl _{groups, (C} 1 -C ₈₎ haloalkyl group , _(C 3 -C ₈₎ halocycloalkyl _{group, (C} 1 -C ₈₎ alkylcarbonyl _{group, (C} 1 -C ₈₎ alkoxycarbonyl _{group, (C} 1 -C ₈₎ alkoxy _(C 1 _-C 8) Alkyl group, aryl group, which may be the same or different (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C ₁ -C ₈ ) alkyl group, ( _{f) (C} 1 -C ₈₎ haloalkyl _{group, (g) (C 1 -C} 8) alkoxy groups, (h) _{(C 1} - ₈₎ haloalkoxy _{group, (i) (C 3 -C} 8) cycloalkyl _(C 1 -C ₈₎ alkoxy _{group, (j) (C 1 -C} 8) alkylthio _{group, (k) (C 1 -C} 8 ) Haloalkylthio group, (l) (C ₁ -C ₈ ) alkylsulfinyl group, (m) (C ₁ -C ₈ ) haloalkylsulfinyl group, (n) (C ₁ -C ₈ ) alkylsulfonyl group, (o) (C ₁ -C ₈ ) haloalkylsulfonyl group, (p) (C ₁ -C ₈ ) alkylcarbonyl group, (q) carboxyl group, (r) (C ₁ -C ₈ ) alkoxycarbonyl group, and (s) phenoxy An aryl group having 1 to 5 substituents selected from a group, a heterocyclic group, which may be the same or different (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) Formyl group, (e) (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈₎ alkoxy _{groups, (h) (C 1 -C} 8) haloalkoxy _{group, (i) (C 3 -C} 8) cycloalkyl _(C 1 -C ₈₎ alkoxy group, (j) _{(C 1} -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C} 1 -C ₈₎ haloalkylsulfinyl group, ( _{n) (C} 1 -C ₈₎ alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl _{group, (p) (C 1 -C} 8) alkylcarbonyl group, (q) a carboxyl group, (r) A heterocyclic group having 1 to 5 substituents selected from (C ₁ -C ₈ ) alkoxycarbonyl group and (s) phenoxy group on the ring. );
(e33) R ⁴ (R ⁵ ) N carbonyl group (wherein R ⁴ and R ⁵ are the same as above);
(e34) R ⁴ (R ⁵ ) NCON (R ⁵ ) group (wherein R ⁴ and R ⁵ are the same as above);
(e35) R ⁴ (R ⁵ ) N (C ₁ -C ₈ ) alkyl group (wherein R ⁴ and R ⁵ are the same as above);
(e36) an aryl group;
(e37) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈ ) alkoxy group, (h) (C ₁ -C ₈ ) haloalkoxy group, (i) (C ₃ -C ₈ ) cycloalkyl ( C ₁ -C ₈₎ alkoxy group, _{(j) (C} 1 -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C 1 -C 8} ) haloalkylsulfinyl _{group, (n) (C 1 -C} 8) alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl group, _(p) (C 1 -C ₈₎ alkylcarbonyl group, (q) a carboxyl _{group, (r) (C 1 -C} 8) alkoxycarbonyl group, and (s). 1 to be selected from a phenoxy group An aryl group having a substituent on the ring;
(e38) aryl _(C 1 -C ₈₎ alkyl group;
(e39) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈ ) alkoxy group, (h) (C ₁ -C ₈ ) haloalkoxy group, (i) (C ₃ -C ₈ ) cycloalkyl ( C ₁ -C ₈₎ alkoxy group, _{(j) (C} 1 -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C 1 -C 8} ) haloalkylsulfinyl _{group, (n) (C 1 -C} 8) alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl group, _(p) (C 1 -C ₈₎ alkylcarbonyl group, (q) a carboxyl _{group, (r) (C 1 -C} 8) alkoxycarbonyl group, and (s). 1 to be selected from a phenoxy group Aryl having substituents on the ring _(C 1 -C ₈₎ alkyl group;
(e40) Heterocyclic group; (Supported in the description)
(e41) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈ ) alkoxy group, (h) (C ₁ -C ₈ ) haloalkoxy group, (i) (C ₃ -C ₈ ) cycloalkyl ( C ₁ -C ₈₎ alkoxy group, _{(j) (C} 1 -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C 1 -C 8} ) haloalkylsulfinyl _{group, (n) (C 1 -C} 8) alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl group, _(p) (C 1 -C ₈₎ alkylcarbonyl group, (q) a carboxyl _{group, (r) (C 1 -C} 8) alkoxycarbonyl group, (s) a phenoxy group, and (t) phenyl methoxide A heterocyclic group having from 1 to 5 substituents selected from a carbonyl group on the ring;
(e42) a heterocyclic (C ₁ -C ₈ ) oxy group;
(e43) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈ ) alkoxy group, (h) (C ₁ -C ₈ ) haloalkoxy group, (i) (C ₃ -C ₈ ) cycloalkyl ( C ₁ -C ₈₎ alkoxy group, _{(j) (C} 1 -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C 1 -C 8} ) haloalkylsulfinyl _{group, (n) (C 1 -C} 8) alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl group, _(p) (C 1 -C ₈₎ alkylcarbonyl group, (q) a carboxyl _{group, (r) (C 1 -C} 8) alkoxycarbonyl group, and (s). 1 to be selected from a phenoxy group Heterocyclic oxy group having a substituent on the ring;
(e44) a heterocyclic (C ₁ -C ₈ ) alkyl group; or
(e45) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈ ) alkoxy group, (h) (C ₁ -C ₈ ) haloalkoxy group, (i) (C ₃ -C ₈ ) cycloalkyl ( C ₁ -C ₈₎ alkoxy group, _{(j) (C} 1 -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C 1 -C 8} ) haloalkylsulfinyl _{group, (n) (C 1 -C} 8) alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl group, _(p) (C 1 -C ₈₎ alkylcarbonyl group, (q) a carboxyl _{group, (r) (C 1 -C} 8) alkoxycarbonyl group, and (s). 1 to be selected from a phenoxy group The substituents showing a heterocyclic _(C 1 -C ₈₎ alkyl groups having on the ring.
W ³ is,
(f1) hydrogen atom;
(f2) a halogen atom;
(f3) a cyano group;
(f4) Formyl group
(f5) a cyano (C ₁ -C ₈ ) alkyl group;
_{(f6) (C 1 ~C 8} ) alkyl group;
_{(f7) (C 2 ~C 8} ) alkenyl group;
_{(f8) (C 2 ~C 8} ) alkynyl group;
_{(f9) (C 2 ~C 8} ) haloalkenyl group;
_{(f10) (C 3 ~C 8} ) cycloalkyl group;
_{(f11) (C 3 ~C 8} ) cycloalkyl _(C 1 _{~C 8)} alkoxy groups;
_{(f12) (C 1 ~C 8} ) alkoxy groups;
_{(f13) (C 1 ~C 8} ) alkoxy _(C 1 _{~C 8)} alkyl group;
_{(f14) (C 1 ~C 8} ) haloalkyl group;
_{(f15) (C 1 ~C 8} ) haloalkoxy group;
_{(f16) (C 3 ~C 8} ) halocycloalkyl group;
_{(f17) (C 3 ~C 8} ) halocycloalkyl _(C 1 _{~C 8)} alkyl group;
_{(f18) (C 1 ~C 8} ) alkylthio group;
_{(f19) (C 1 ~C 8} ) alkylsulfinyl group;
_{(f20) (C 1 ~C 8} ) alkylsulfonyl group;
(f21) a (C ₁ -C ₈ ) alkylthio (C ₁ -C ₈ ) alkyl group;
(f22) a (C ₁ -C ₈ ) alkylsulfinyl (C ₁ -C ₈ ) alkyl group;
(f23) a (C ₁ -C ₈ ) alkylsulfonyl (C ₁ -C ₈ ) alkyl group;
_{(f24) (C 1 ~C 8} ) haloalkylthio group;
(f25) a (C ₁ -C ₈ ) haloalkylsulfinyl group;
_{(f26) (C 1 ~C 8} ) haloalkylsulfonyl groups;
_{(f27) (C 1 ~C 8} ) alkoxycarbonyl group;
_{(f28) (C 2 ~C 8} ) alkenyloxycarbonyl group;
_{(f29) (C 1 ~C 8} ) alkoxycarbonyl _(C 1 _{~C 8)} alkyl group;
_{(f30) (C 1 ~C 8} ) alkylcarbonyl group;
_{(f31) (C 3 ~C 8} ) cycloalkyl group;
(f32) R ⁴ (R ⁵ ) N carbonyl group (wherein R ⁴ and R ⁵ are the same as above);
(f33) R ⁴ (R ⁵ ) N sulfonyl group (wherein R ⁴ and R ⁵ are the same as above);
(f34) an aryl group;
(f35) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈ ) alkoxy group, (h) (C ₁ -C ₈ ) haloalkoxy group, (i) (C ₃ -C ₈ ) cycloalkyl ( C ₁ -C ₈₎ alkoxy group, _{(j) (C} 1 -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C 1 -C 8} ) haloalkylsulfinyl _{group, (n) (C 1 -C} 8) alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl group, _(p) (C 1 -C ₈₎ alkylcarbonyl group, (q) a carboxyl _{group, (r) (C 1 -C} 8) alkoxycarbonyl group, and (s). 1 to be selected from a phenoxy group An aryl group having a substituent on the ring;
(f36) aryl _(C 1 -C ₈₎ alkyl group;
(f37) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈ ) alkoxy group, (h) (C ₁ -C ₈ ) haloalkoxy group, (i) (C ₃ -C ₈ ) cycloalkyl ( C ₁ -C ₈₎ alkoxy group, _{(j) (C} 1 -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C 1 -C 8} ) haloalkylsulfinyl _{group, (n) (C 1 -C} 8) alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl group, _(p) (C 1 -C ₈₎ alkylcarbonyl group, (q) a carboxyl _{group, (r) (C 1 -C} 8) alkoxycarbonyl group, and (s). 1 to be selected from a phenoxy group Aryl having substituents on the ring _(C 1 -C ₈₎ alkyl group;
(f38) a heterocyclic group;
(f39) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈ ) alkoxy group, (h) (C ₁ -C ₈ ) haloalkoxy group, (i) (C ₃ -C ₈ ) cycloalkyl ( C ₁ -C ₈₎ alkoxy group, _{(j) (C} 1 -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C 1 -C 8} ) haloalkylsulfinyl _{group, (n) (C 1 -C} 8) alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl group, _(p) (C 1 -C ₈₎ alkylcarbonyl group, (q) a carboxyl _{group, (r) (C 1 -C} 8) alkoxycarbonyl group, and (s). 1 to be selected from a phenoxy group Heterocyclic group having a substituent on the ring;
(f40) heterocyclic carbonyl group;
(f41) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈ ) alkoxy group, (h) (C ₁ -C ₈ ) haloalkoxy group, (i) (C ₃ -C ₈ ) cycloalkyl ( C ₁ -C ₈₎ alkoxy group, _{(j) (C} 1 -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C 1 -C 8} ) haloalkylsulfinyl _{group, (n) (C 1 -C} 8) alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl group, _(p) (C 1 -C ₈₎ alkylcarbonyl group, (q) a carboxyl _{group, (r) (C 1 -C} 8) alkoxycarbonyl group, and (s). 1 to be selected from a phenoxy group Heterocyclic carbonyl group having a substituent on the ring;
(f42) a heterocyclic (C ₁ -C ₈ ) alkyl group; or
(f43) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈ ) alkoxy group, (h) (C ₁ -C ₈ ) haloalkoxy group, (i) (C ₃ -C ₈ ) cycloalkyl ( C ₁ -C ₈₎ alkoxy group, _{(j) (C} 1 -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C 1 -C 8} ) haloalkylsulfinyl _{group, (n) (C 1 -C} 8) alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl group, _(p) (C 1 -C ₈₎ alkylcarbonyl group, (q) a carboxyl _{group, (r) (C 1 -C} 8) alkoxycarbonyl group, and (s). 1 to be selected from a phenoxy group The substituents showing a heterocyclic _(C 1 -C ₈₎ alkyl groups having on the ring.
W ⁴ , W ⁵ , W ⁶ , and W ⁷ may be the same or different,
(g1) hydrogen atom;
(g2) a halogen atom;
(g3) a cyano group;
(g4) Formyl group
_{(g5) (C 1 ~C 8} ) alkyl group;
_{(g6) (C 1 ~C 8} ) haloalkyl group;
_{(g7) (C 1 ~C 8} ) alkoxy group; or
_(g8) shows a _(C 1 _{~C 8)} haloalkoxy group.
R ¹ is
_{(h1) (C 1 ~C 8} ) alkyl group;
_{(h2) (C 2 ~C 8} ) alkenyl group;
_{(h3) (C 2 ~C 8} ) alkynyl group;
_{(h4) (C 3 ~C 8} ) cycloalkyl group;
(h5) a cyano (C ₁ -C ₈ ) alkyl group;
_{(h6) (C 3 ~C 8} ) cycloalkyl _(C 1 _{~C 8)} alkyl group;
(h7) hydroxy _(C 1 _{~C 8)} alkyl group;
(h8) (C ₁ -C ₈ ) alkoxy (C ₁ -C ₈ ) alkyl groups;
(h9) a (C ₁ -C ₈ ) alkylthio (C ₁ -C ₈ ) alkyl group;
(h10) a (C ₁ -C ₈ ) alkylsulfinyl (C ₁ -C ₈ ) alkyl group;
(h11) a (C ₁ -C ₈ ) alkylsulfonyl (C ₁ -C ₈ ) alkyl group;
(h12) aryl _(C 1 _{~C 8)} alkyl group;
(h13) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C ₁ -C ₈ ) alkyl group, (f) (C ₁ -C ₈ ) haloalkyl group, (g) (C ₁ -C ₈ ) alkoxy group, (h) (C ₁ -C ₈ ) haloalkoxy group, (i) (C ₃ -C ₈ ) cycloalkyl ( C ₁ -C ₈₎ alkoxy group, _{(j) (C} 1 -C ₈₎ alkylthio group, _{(k) (C} 1 -C ₈₎ haloalkylthio group, _{(l) (C} 1 -C ₈₎ alkylsulfinyl group, _{(m) (C 1 -C 8} ) haloalkylsulfinyl _{group, (n) (C 1 -C} 8) alkylsulfonyl _{groups, (o) (C 1 -C} 8) haloalkylsulfonyl group, _(p) (C 1 -C ₈₎ alkylcarbonyl group, (q) a carboxyl group, _{(r) (C} 1 -C ₈₎ alkoxycarbonyl ^{group, (s) R 4 (R} 5) N group (wherein, . ⁴ and ^{R 5} are the same as defined above), and (t) aryl having from 1 to 5 substituents on the ring which is selected from a phenoxy group _(C 1 -C ₈₎ alkyl group;
(h14) R ⁴ (R ⁵ ) NCO ₂ (C ₁ -C ₈ ) alkyl group (wherein R ⁴ and R ⁵ are the same as above).
(h15) R ⁴ (R ⁵ ) NCO (C ₁ -C ₈ ) alkyl group (wherein R ⁴ and R ⁵ are the same as above); or
(h16) R ⁴ (R ⁵ ) NCO (R ⁴ ) N (C ₁ -C ₈ ) alkyl group (wherein R ⁴ and R ⁵ are the same as above). "
R ² is
(i1) hydrogen atom;
_{(i2) (C 1 -C 8} ) alkyl group;
_{(i3) (C 3 -C 8} ) cycloalkyl group; or
_{(i4) (C 3 -C 8} ) a cycloalkyl _(C 1 -C ₈₎ alkyl group, or
(i5) R ¹ and R ² are bonded to each other and contain one nitrogen atom, and further contain 1 to 2 identical or different heteroatoms selected from an oxygen atom, a nitrogen atom and a sulfur atom. Also good 5-8 membered saturated nitrogen-containing heterocycles can be formed.
R ³ is
(j1) hydrogen atom;
_{(j2) (C 1 -C 8} ) alkyl group;
_{(j3) (C 3 -C 8} ) cycloalkyl group; or
_{(j4) (C 3 -C 8} ) cycloalkyl _(C 1 -C ₈₎ alkyl group;
Indicates. ] Or a salt thereof (provided that N ^1- {2-chloro-4-[(6-heptafluoroisopropyl) -2- (trifluoromethyl) -1H-imidazo [4,5-C except (2-methyl-1- (methylthio) propan-2-yl) phthalamide -] pyridin-1-yl) methyl] phenyl} -3-iodo ^-N 2. ). The phthalamide derivative according to claim 1, represented by the following, or a salt thereof:
X ¹ is
(a1) a halogen atom;
_{(a6) (C 1 ~C 8} ) alkylthio group;
(a8) a (C ₁ -C ₈ ) alkylsulfinyl group; or
(a10) a (C ₁ -C ₈ ) alkylsulfonyl group, and X ² is
(b1) is a hydrogen atom,
Y is
(c1) hydrogen atom;
(c2) a halogen atom;
(c3) a cyano group;
_{(c4) (C 1 ~C 8} ) alkyl group;
_{(c6) (C 1 ~C 8} ) alkoxy groups;
_{(c8) (C 1 ~C 8} ) alkylthio group; or
(c10) a (C ₁ -C ₈ ) alkylsulfinyl group,
W ² is,
(e1) hydrogen atom;
(e3) a cyano group;
_{(e6) (C 1 ~C 8} ) alkyl group;
_{(e10) (C 3 ~C 8} ) cycloalkyl group;
_{(e11) (C 3 ~C 8} ) cycloalkyl _(C 1 _{~C 8)} alkoxy groups;
_{(e12) (C 1 ~C 8} ) alkoxy groups;
_{(e13) (C 1 ~C 8} ) alkoxy _(C 1 _{~C 8)} alkyl group;
_{(e14) (C 1 ~C 8} ) haloalkyl group;
_{(e15) (C 1 ~C 8} ) haloalkoxy group;
_{(e18) (C 1 ~C 8} ) alkylthio group;
_{(e19) (C 1 ~C 8} ) alkylsulfinyl group;
_{(e20) (C 1 ~C 8} ) alkylsulfonyl group;
_{(e27) (C 1 ~C 8} ) alkoxycarbonyl group;
(e32) R ⁴ (R ⁵ ) N group (wherein R ⁴ and R ⁵ may be the same or different, a hydrogen atom, (C ₁ -C ₈ ) alkyl group, (C ₃ -C ₈ ) cycloalkyl) A group, (C ₁ -C ₈ ) alkylcarbonyl group, (C ₁ -C ₈ ) alkoxycarbonyl group, or (C ₁ -C ₈ ) alkoxy (C ₁ -C ₈ ) alkyl group);
(e33) R ⁴ (R ⁵ ) N carbonyl group (wherein R ⁴ and R ⁵ are the same as above);
(e34) R ⁴ (R ⁵ ) NCON (R ⁵ ) group (wherein R ⁴ and R ⁵ are the same as above);
(e36) an aryl group;
(e37) aryl group which may be the same or different, and (a) an aryl group having 1 to 5 substituents selected from a halogen atom and (f) (C ₁ -C ₈ ) haloalkyl group on the ring;
(e40) a heterocyclic group;
(e41) may be identical or different, a heterocyclic group having a _{(r) (C 1 -C 8} ) alkoxycarbonyl group, and (t) 1 to 5 substituents selected from phenylmethoxy carbonyl group on the ring; Or
(e42) a heterocyclic (C ₁ -C ₈ ) oxy group,
W ³ is,
(f1) hydrogen atom;
(f5) a cyano (C ₁ -C ₈ ) alkyl group;
_{(f6) (C 1 ~C 8} ) alkyl group;
_{(f7) (C 2 ~C 8} ) alkenyl group;
_{(f8) (C 2 ~C 8} ) alkynyl group;
_{(f10) (C 3 ~C 8} ) cycloalkyl group;
_{(f11) (C 3 ~C 8} ) cycloalkyl _(C 1 _{~C 8)} alkoxy groups;
_{(f13) (C 1 ~C 8} ) alkoxy _(C 1 _{~C 8)} alkyl group;
_{(f14) (C 1 ~C 8} ) haloalkyl group;
(f21) a (C ₁ -C ₈ ) alkylthio (C ₁ -C ₈ ) alkyl group;
(f22) a (C ₁ -C ₈ ) alkylsulfinyl (C ₁ -C ₈ ) alkyl group;
(f23) a (C ₁ -C ₈ ) alkylsulfonyl (C ₁ -C ₈ ) alkyl group;
_{(f27) (C 1 ~C 8} ) alkoxycarbonyl group;
_{(f29) (C 1 ~C 8} ) alkoxycarbonyl _(C 1 _{~C 8)} alkyl group;
_{(f30) (C 1 ~C 8} ) alkylcarbonyl group;
(f32) R ⁴ (R ⁵ ) N carbonyl group (wherein R ⁴ and R ⁵ are the same as above);
(f33) R ⁴ (R ⁵ ) N sulfonyl group (wherein R ⁴ and R ⁵ are the same as above);
(f38) a heterocyclic group;
(f40) a heterocyclic carbonyl group; or
(f42) a heterocyclic (C ₁ -C ₈ ) alkyl group,
W ⁴ , W ⁵ , W ⁶ , and W ⁷ may be the same or different,
(g1) a hydrogen atom; or
(g6) a (C ₁ -C ₈ ) haloalkyl group,
R ¹ is
_{(h1) (C 1 ~C 8} ) alkyl group;
_{(h4) (C 3 ~C 8} ) cycloalkyl group;
(h5) a cyano (C ₁ -C ₈ ) alkyl group;
(h7) hydroxy _(C 1 _{~C 8)} alkyl group;
(h8) (C ₁ -C ₈ ) alkoxy (C ₁ -C ₈ ) alkyl groups;
(h9) a (C ₁ -C ₈ ) alkylthio (C ₁ -C ₈ ) alkyl group;
(h10) a (C ₁ -C ₈ ) alkylsulfinyl (C ₁ -C ₈ ) alkyl group;
(h11) a (C ₁ -C ₈ ) alkylsulfonyl (C ₁ -C ₈ ) alkyl group;
(h12) aryl _(C 1 _{~C 8)} alkyl group; or
(h14) R ⁴ (R ⁵ ) NCO ₂ (C ₁ -C ₈ ) alkyl group (wherein R ⁴ and R ⁵ are the same as above),
R ² is
(i1) a hydrogen atom; or
(i2) is a (C ₁ -C ₈ ) alkyl group; or
(i5) R ¹ and R ² are bonded to each other and contain one nitrogen atom, and further contain 1-2 identical or different heteroatoms selected from an oxygen atom, a nitrogen atom, and a sulfur atom. Can form a good 5- to 8-membered saturated nitrogen-containing heterocycle,
R ³ is
(j1) a hydrogen atom; or
(j2) a (C ₁ -C ₈ ) alkyl group. The phthalamide derivative according to claim 2, represented by the following, or a salt thereof:
X ¹ is
(a1) a halogen atom; or
(a10) a (C ₁ -C ₈ ) alkylsulfonyl group, and X ² is
(b1) is a hydrogen atom,
Y is
(c1) hydrogen atom;
(c2) a halogen atom; or
_{(c4) (C 1 ~C 8} ) alkyl group,
W ² is,
_{(e12) (C 1 ~C 8} ) alkoxy group; or
(e14) a (C ₁ -C ₈ ) haloalkyl group,
W ³ is,
(f1) hydrogen atom;
_{(f6) (C 1 ~C 8} ) alkyl group;
_{(f8) (C 2 ~C 8} ) alkynyl; or
(f14) a (C ₁ -C ₈ ) haloalkyl group,
W ⁴ , W ⁵ , W ⁶ , and W ⁷ may be the same or different,
(g1) a hydrogen atom; or
(g6) a (C ₁ -C ₈ ) haloalkyl group,
R ¹ is
(h9) a (C ₁ -C ₈ ) alkylthio (C ₁ -C ₈ ) alkyl group;
(h10) a (C ₁ -C ₈ ) alkylsulfinyl (C ₁ -C ₈ ) alkyl group; or
_{(h11) (C 1 ~C 8} ) alkylsulfonyl _(C 1 _{~C 8)} alkyl group,
R ² is
(i1) is a hydrogen atom,
R ³ is
(j1) A hydrogen atom.   An agricultural and horticultural insecticide comprising the phthalamide derivative according to any one of claims 1 to 3 or a salt thereof as an active ingredient.   A method for using an agricultural and horticultural insecticide, comprising treating a plant or soil with the phthalamide derivative according to any one of claims 1 to 3 or a salt thereof as an active ingredient of an agricultural and horticultural insecticide.   A method for using an agricultural and horticultural insecticide, comprising treating a plant or soil with the phthalamide derivative according to any one of claims 1 to 3 or a salt thereof as an active ingredient of an agricultural and horticultural insecticide. General formula (3):

[Wherein, Y, Z ¹ , Z ² , Z ³ , A and Q are the same as defined in claim 1. ] The aniline derivative concerning the intermediate of the phthalamide derivative represented by these, or its salt.