WO2022092084A1

WO2022092084A1 - Fused heterocycle derivative and herbicide containing same as active ingredient

Info

Publication number: WO2022092084A1
Application number: PCT/JP2021/039485
Authority: WO
Inventors: 幸浩榎本; 和貴野城; 貴史塩澤; 崇史佐藤; 貴章平井; 愛理太田; 匡毅羽根
Original assignee: クミアイ化学工業株式会社
Priority date: 2020-10-29
Filing date: 2021-10-26
Publication date: 2022-05-05
Also published as: AR123931A1; JP2023175057A; TW202233590A

Abstract

The present invention provides a novel fused heterocycle derivative or an agriculturally acceptable salt thereof and an herbicide containing the same as an active ingredient.　Provided are a fused heterocycle derivative represented by general formula [I] (in general formula [I], Q represents Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, or Q-8, R⁷ represents a halogen atom, a C₁-C₆ haloalkyl group, a cyano group, etc., Z represents an oxygen atom or a sulfur atom, A represents N or C-R¹³, R¹³ represents a hydrogen atom, a halogen atom, or a cyano group) or a salt thereof and an herbicide characterized by containing the same as an active ingredient.

Description

Condensed heterocyclic derivative and herbicide containing it as an active ingredient

The present invention relates to a novel condensed heterocyclic derivative or an agriculturally acceptable salt thereof, and a herbicide containing the derivative as an active ingredient.

Conventionally, the following are known as fused heterocyclic derivatives and the like (see, for example, Patent Documents 1 to 8).

Patent Documents 1 and 2 describe pyrimidinyloxy-condensed heterocyclic derivatives having a herbicidal effect.

Patent Document 3 describes a pyrimidinyloxy or a pyridinyloxy-condensed heterocyclic derivative having a Kv3 channel inhibitory activity.

Patent Document 4 describes a 7- (pyridin-2-yloxy) -1H-benzimidazole derivative having an antifungal effect.

Patent Document 5 describes a 7- (pyridin-2-yloxy) -1H-indazole derivative having a tyrosine kinase inhibitory activity.

Patent Document 6 describes a 7- (pyridin-2-yloxy) -1H-indole derivative having a collagen synthesis inhibitory activity.

Patent Documents 7 and 8 describe 7- (pyridin-2-yloxy) indoline-2-one derivatives having bromodomain inhibitory activity.

International Publication No. 2018/20164 International Publication No. 2021/094416 International Publication No. 2012/076877 International Publication No. 2008/101682 US Publication No. 2006/0079564 International Publication No. 2009/057811 International Publication No. 2018/109271 International Publication No. 2016/203112

The compounds described in Patent Documents 1 and 2 are not sufficient in terms of herbicidal effect and the like.

In the compound described in Patent Document 3, the 5-position of the pyrimidine ring or the pyridine ring is limited to the 2,5-dioxoimidazolidine-1-yl group, and Patent Document 3 does not pay attention to the herbicidal effect. ..

In the compound described in Patent Document 4, the 5-position of the pyridine ring is limited to the formimide group, and Patent Document 4 does not pay attention to the herbicidal effect.

In the compound described in Patent Document 5, the 3-position of the indazole ring is limited to the 1H-benzimidazol-2-yl group, and Patent Document 5 does not pay attention to the herbicidal effect.

In the compound described in Patent Document 6, the 5-position of the pyridine ring is limited to a benzamide group or the like, and Patent Document 6 does not pay attention to the herbicidal effect.

The compounds described in Patent Documents 7 and 8 are limited to derivatives in which the 5-position of the indolin-2-one ring is substituted with a 1-phenyl-1H-pyrazole-5-yl group, a phenylsulfonamide group, or the like. , Patent Documents 7 and 8 do not pay attention to the herbicidal effect.

In the cultivation of useful plants, the outbreak of various weeds has a significant impact on the production efficiency of plants, crops and products, so in order to control these weeds, weeds with better properties at lower dosages. The creation of agents is required. In addition, there are increasing demands for the safety of chemical substances and their impact on the environment, and the development of safer herbicides is desired.

The present invention has been made in view of the above circumstances, and an object thereof is to produce various weeds generated in upland fields, orchards, paddy fields, non-agricultural lands, etc. without causing chemical damage to useful plants. It is an object of the present invention to provide a compound having a herbicidal activity that can be controlled with a low dose, and a herbicide containing the compound.

In order to achieve the above object, the present inventors synthesized a large number of condensed heterocyclic derivatives and diligently investigated their herbicidal activity and usefulness. As a result, by applying the fused heterocyclic derivative represented by the following general formula [I] (hereinafter referred to as “the compound of the present invention”) to the plant, various weeds can be controlled for a long period of time. It was found that a remarkable herbicidal effect was exhibited without causing chemical damage to plants, and further research was continued to complete the present invention.

That is, the present invention has the following gist.
(1) General formula [I]

[In the general formula [I],
Q indicates Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7 or Q-8.

R ¹ is a hydrogen atom, a C ₁ to C ₆ alkyl group (the group may be mono-substituted or poly-substituted by R ⁸ ), a C ₂ -C ₆ alkenyl group (the group may be mono-substituted or poly-substituted by R ⁸ ). Substituted) _, _C2 _- C6 alkynyl group (the group may be mono-substituted or poly ^- substituted with R8), C3 _- C6 cycloalkyl group ⁽ the group may be mono-substituted or poly-substituted with R8). Indicates a poly-substituted), phenyl group (the group may be mono- or poly-substituted by R ⁹ ) or a heteroaryl group (the group may be mono- or poly-substituted by R ⁹ ). ,
R ⁸ is a halogen atom, C ₁ to C ₆ alkyl group, C ₁ to C ₆ haloalkyl group, C ₃ to C ₆ cycloalkyl group, C ₃ to C ₆ halocycloalkyl group, formyl group, C ₁ to C ₆ Alkylcarbonyl group, C1 to C6 haloalkylcarbonyl group, C3 to C6 cycloalkylcarbonyl group, benzoyl group (the group may be ^{mono- or poly-substituted with R 9} ₎ _, ^{-C (R 10} ₎ ₌ NOR ¹¹ , carboxy group, C ₁ to C ₆ alkoxycarbonyl group, _C ₁ to C ₆ _{haloalkoxycarbonyl} group, aminocarbonyl group, C1 to C6 alkylaminocarbonyl group (even if the amino group is substituted with ^R12 ) Good), C _1-6 haloalkylaminocarbonyl group (the amino group may be substituted with R ¹² ), pyrrolidine- ₁ -ylcarbonyl group (the group may be mono-substituted or poly-substituted with R ⁹ ). ), Piperidine-1-ylcarbonyl group (the group may be mono-substituted or poly-substituted with R ⁹ ), hydroxy group, C ₁ to C ₆ alkoxy group, C ₃ to C ₆ alkenyloxy group, C ₃ to C ₆ alkynyloxy group, C ₁ to C ₆ haloalkoxy group, C ₃ to C ₆ cycloalkoxy group, C ₃ to C ₆ halocycloalkoxy group, C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkoxy group, C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkoxy group, phenoxy group (the group may be mono-substituted or poly-substituted with R ⁹ ), phenyl C ₁ to C ₆ alkoxy group (the phenyl group is R ⁹ ). ( _Can be _mono _- _substituted _or _poly _- _substituted with C1 to _C6 _{haloalkylsulfinyl} groups _, C1 to _C6 _{haloalkylsulfonyl} groups _, C3 to _C6 _{cycloalkylthio} groups _, C3 to _C6 cycloalkylsulfinyl groups, C3 to C6 cycloalkylsulfonyl groups _, C3 to _C ₆ _{halocycloalkylthio} group _, C3 to C6 _{halocycloalkylsulfinyl} group _, C3 to C6 _{halocycloalkylsulfonyl} group _, C3 to _C6 cycloalkyl C1 to _C6 alkylthio group, C3 to _C6cyclo Alkyl C ₁ to C ₆ alkyl sulfinyl groups, C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkyl sulfonyl groups, C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkylthio groups, C ₃ to C ₆ halocycloalkyl C ₁ ~ C ₆ alkyl sulfinyl group, C ₃ ~ C ₆ ^{halocycloalkyl} C ₁ ~ C ₆ alkyl sulfonyl group, phenylthio group (the group may be mono-substituted or poly-substituted by R9), phenyl sulfinyl group (the group). May be mono-substituted or poly-substituted with R ⁹ ), a phenylsulfonyl group (the group may be mono- or poly _- substituted with R ⁹ ), an amino group, _a C1-6 alkylamino group (the amino). The group may be substituted with R ¹² ), a C ₁ to C ₆ haloalkylamino group (the amino group may be substituted with R ¹² ), a C ₁ to C ₆ alkylcarbonylamino group (the amino group may be R 12). ¹² may be substituted) _, C ₁ to C ₆ haloalkylcarbonylamino groups (the amino groups may be substituted by ^R12 ), C3 to _C6 cycloalkylcarbonylamino groups (the amino groups may be ^R12 ). (May be substituted with R ⁹ ), phenylcarbonylamino group (the phenyl group may be mono-substituted or poly-substituted with R 9, and the amino group may be substituted with R ¹² ), C ₁ to C ₆ alkoxy. A carbonylamino group (the amino group may be substituted with R ¹² ), a C ₁ to C ₆ haloalkoxycarbonyl amino group (the amino group may be substituted with R ¹² ), a C ₁ to C ₆ alkylamino. A carbonylamino group (the amino group may be substituted with R ¹² ), a C ₁ to C ₆ haloalkylaminocarbonylamino group (the amino group may be substituted with R ¹² ), a C ₁ to C ₆ alkylsulfonyl. Amino group (the amino group may be substituted with R ¹² ), C ₁ to C ₆ haloalkylsulfonylamino group (the amino group may be substituted with R ¹² ), C ₃ to C ₆ cycloalkylsulfonylamino. A group (the amino group may be substituted with R ¹² ), a phenylsulfonyl amino group (the phenyl group may be mono-substituted or poly-substituted with R ⁹ , and the amino group may be substituted with R ¹² ). ), Tri (C ₁ to C ₆ alkyl) silyl group, phenyl group (the group is ^motorized by R9) No-substituted or poly-substituted), 1,3-benzodioxolyl group (the group may be mono-substituted or poly-substituted with R ⁹ ), heteroaryl group (the group may be mono-substituted with R ⁹ ). Alternatively, it may be poly-substituted), a heteroaryloxy group (the group may be mono-substituted or poly-substituted with R ⁹ ), a heterocycloalkyl group (the group may be mono- or poly-substituted with R ⁹ ). Good), showing a cyano group, a nitro group or a thiocyanato group,
R ⁹ is a halogen atom, C ₁ to C ₆ alkyl group, C ₂ to C ₆ alkenyl group, C ₂ to C ₆ alkynyl group, C ₁ to C ₆ haloalkyl group, C ₃ to C ₆ cycloalkyl group, C ₃ ~ C ₆ halocycloalkyl group, formyl group, hydroxy group, C ₁ ~ C ₆ alkoxy group, C ₁ ~ C ₆ haloalkoxy group, thiol group, C ₁ ~ C ₆ alkylthio group, C ₁ ~ C ₆ alkyl sulfinyl group , C ₁ to C ₆ alkylsulfonyl groups, _C ₁ to _C ₆ haloalkylthio groups, C1 to _C6 haloalkylsulfinyl groups, C1 to _C6 haloalkylsulfonyl groups, cyano groups or nitro groups.
R ¹⁰ is a hydrogen atom, C ₁ to C ₆ alkyl group, C ₂ to C ₆ alkenyl group, C ₂ to C ₆ alkynyl group, C ₁ to C ₆ haloalkyl group, C ₃ to C ₆ cycloalkyl group, phenyl group. (The group may be mono-substituted or poly-substituted with R ⁹ ) or a heteroaryl group (the group may be mono- or poly-substituted with R ⁹ ).
R ¹¹ is a hydrogen atom, C ₁ to C ₆ alkyl group, C ₂ to C ₆ alkenyl group, C ₂ to C ₆ alkynyl group, C ₁ to C ₆ haloalkyl group, C ₃ to C ₆ cycloalkyl group or C ₃ Representing a ~ C6 _{halocycloalkyl} group,
R ¹² is a C ₁ to C ₆ alkyl group, a C ₂ to C ₆ alkenyl group, a C ₂ to C ₆ alkynyl group, a C ₁ to C ₆ haloalkyl group, a C ₃ to C ₆ cycloalkyl group, and a C ₃ to C ₆ . _{Halocycloalkyl} group, C3 to C6 cycloalkyl C1 to _C6 alkyl group, C1 to _C _6alkoxy C1 to _C6 alkyl group, _C1 to _C ₆ _haloalkoxy _C1 to _C6 alkyl group, _cyano C ₁ to C ₆ alkyl groups, C ₁ to C ₆ alkyl carbonyl groups, C ₁ to C ₆ haloalkyl carbonyl groups, C ₁ to C ₆ alkoxycarbonyl groups, C ₁ to C ₆ halo alkoxycarbonyl groups, C ₁ to C ₆ An alkylaminocarbonyl group, a C1 to C6 ^{haloalkylaminocarbonyl} group or a benzoyl group (the group may be mono _- substituted or poly _- substituted by R9) is shown.
R ² is a hydrogen atom, a halogen atom, a C ₁ to C ₆ alkyl group, a C ₂ to C ₆ alkenyl group, a C ₂ to C ₆ alkynyl group, a C ₁ to C ₆ haloalkyl group, and a C ₃ to C ₆ cycloalkyl group. , C ₃ to C ₆ _{halocycloalkyl} groups, formyl groups _, _C ₁ to C ₆ alkylcarbonyl groups, C1 to C6 haloalkylcarbonyl groups, ^{C3 to C6 cycloalkylcarbonyl groups, -C (R 10} ₎ = NOR ¹¹ , carboxy group, C ₁ to C ₆ alkoxycarbonyl group, C ₁ to C ₆ _{haloalkoxycarbonyl} group, aminocarbonyl group, aminothiocarbonyl group, C1 to C6 alkylaminocarbonyl group (the amino group is based _on ^R12 ). C1 to _C6 _{haloalkylaminocarbonyl} group (the amino group may be substituted by ^R12 ), hydroxy group, C1 to _C6 alkoxy group _, C3 to _C6 _alkenyloxy group. , C ₃ to C ₆ alkynyloxy groups, C ₁ to C ₆ haloalkoxy groups, C ₃ to C ₆ cycloalkoxy groups, C ₃ to C ₆ halocycloalkoxy groups, C ₃ to C ₆ cycloalkyls C ₁ to C ₆ Alkoxy groups, C ₃ to C ₆ ^{halocycloalkyl} C ₁ to C ₆ alkoxy groups, phenyl C ₁ to C ₆ alkoxy groups (the phenyl groups may be mono-substituted or poly-substituted by R9), heteroaryloxy groups. (The group may be mono-substituted or poly-substituted with R ⁹ ), C ₁ to C ₆ alkylthio groups, C ₁ to C ₆ alkyl sulfinyl groups, C ₁ to C ₆ alkyl sulfonyl groups, C ₁ to C ₆ halos. _Alkylthio groups, C1 to C6 _{haloalkylsulfinyl} groups, C1 to _C6 _{haloalkylsulfonyl} groups, amino groups, _C1 to _C6 alkylamino groups (the amino groups may be substituted with ^R12 ), _C1 to C ₆ haloalkylamino group (the amino group may be substituted with R ¹² ), C ₁ to C ₆ alkylcarbonylamino groups (the amino group may be substituted with R ¹² ), C ₁ to C ₆ haloalkyl. A carbonylamino group (the amino group may be substituted with R ¹² ), a C ₃ to C ₆ cycloalkylcarbonyl amino group (the amino group may be substituted with R ¹² ), a C ₁ to C ₆ alkoxycarbonyl. Amino group (the amino group is R ¹² may be substituted), C ₁ to C ₆ alkylsulfonylamino groups (the amino groups may be substituted by R ¹² ), C ₁ to C ₆ haloalkylsulfonyl amino groups (the amino groups may be substituted by R ¹² ). Substituted), C ₃ _- C6 cycloalkylsulfonylamino group (the amino group may be substituted with R ¹² ), phenyl group (the group may be mono-substituted or poly-substituted with R ⁹ ). ), ^Heteroaryl group (the group may be mono-substituted or poly-substituted by R9), cyano group or nitro group.
R ³ is a hydrogen atom, a halogen atom, a C ₁ to C ₆ alkyl group, a C _{2 to C 6 alkoxy group, a C 2} _{to C 6} _alkoxyyl _group , a C ₁ to C ₆ haloalkyl group, and a C ₃ to C ₆ cycloalkyl group. , C ₃ to C ₆ halocycloalkyl groups, C ₁ to C ₆ alkoxy C ₁ to C ₆ alkyl groups, C ₁ to C ₆ haloalkoxy C ₁ to C ₆ alkyl groups, C ₁ to C ₆ alkylthios C ₁ to C ₆ Alkoxy Group, C ₁ to C ₆ Alkoxy Sulfinyl C ₁ to C ₆ Alkoxy Group, C ₁ to C ₆ Alkoxysulfonyl C ₁ to C ₆ Alkoxy Group, C ₁ to C ₆ Haloalkylthio C ₁ to C ₆ Alkoxy Group, C ₁ to C ₆ haloalkylsulfinyl C ₁ to C ₆ alkyl groups, C ₁ to C ₆ haloalkylsulfonyl C ₁ to C ₆ alkyl groups, cyano C ₁ to C ₆ alkyl groups, formyl groups, C ₁ to C ₆ alkyl carbonyl groups, C ₁ to C ₆ haloalkyl carbonyl group, C ₃ to C ₆ cycloalkyl carbonyl group, -C (R ¹⁰ ) = NOR ¹¹ , carboxy group, C ₁ to C ₆ alkoxy carbonyl group, C ₁ to C ₆ haloalkoxy carbonyl group , Aminocarbonyl group, _{aminothiocarbonyl} group, C1 to _C6 alkylaminocarbonyl group (the amino group may be substituted with ^R12 ), C1 to _C6 _{haloalkylaminocarbonyl} group (the amino group is ^R12 ). , Hydroxyl group, C1 to C6 alkoxy group, C3 to C6 _alkoxyoxy group _, C3 to C6 _alkynyloxy group _, C1 to _C6 _haloalkoxy group _, _C3 to _C ₆ cycloalkoxy groups, C ₃ to C ₆ halocycloalkoxy groups, C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkoxy groups, C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkoxy groups, phenyl C ₁ to C ₆ alkoxy group (the phenyl group may be mono-substituted or poly-substituted with R ⁹ ), heteroaryloxy group (the group may be mono-substituted or poly-substituted with R ⁹ ), C ₁ -C ₆ _Alkoxythio _groups , _C1 to _C6 _{alkylsulfinyl} groups, _C1 to _C6 alkylsulfonyl groups, C1 to _C6 _{haloalkylthio} groups, C1 to _C6 haloalkylsulfinyl groups, C1 to C6 haloalkylsulfoni Lu groups, amino groups, C ₁ to C ₆ alkylamino groups (the amino groups may be substituted with R ¹² ), C ₁ to C ₆ haloalkyl amino groups (the amino groups may be substituted with R ¹² ). ), _C ₁ to C ₆ alkylcarbonylamino groups (the amino groups may be substituted with ^R12 ), C1 to _C6 haloalkylcarbonylamino groups (the amino groups may be substituted with ^R12 ), _C ₃ to C ₆ cycloalkylcarbonylamino groups (the amino groups may be substituted with ^R12 ), C1 to _C6 alkoxycarbonylamino groups (the amino groups may be substituted with ^R12 ), C. ₁ to _C ₆ alkylsulfonylamino groups (the amino groups may be substituted with ^R12 ), C1 to _C6 haloalkylsulfonylamino groups (the amino groups may be substituted with ^R12 ) _, C3 to C6 cycloalkylsulfonylamino group (the amino group may be substituted with R ₁₂ ), phenyl group (the group may be ^{mono-substituted or poly-substituted with R 9} ⁾ , heteroaryl group (the group may be R). ⁹ ), mono- or poly-substituted), showing a cyano or nitro group,
^R4 is independently a halogen atom, C ₁ to C ₆ alkyl group, C ₁ to C ₆ haloalkyl group, hydroxy group, C ₁ to C ₆ alkoxy group, C ₁ to C ₆ haloalkoxy group, cyano group or nitro. Show the group,
m represents an integer of 0, 1, 2 or 3
Y represents an oxygen atom or a sulfur atom.
R ⁵ independently contains a hydrogen atom, a halogen atom, a C ₁ to C ₆ alkyl group, a C ₁ to C ₆ haloalkyl group, a C ₃ to C ₆ cycloalkyl group, a C ₃ to C ₆ halocycloalkyl group, and a hydroxy group. , C ₁ to C ₆ alkoxy groups, C ₁ to C ₆ haloalkoxy groups, heteroaryloxy groups (the groups may be mono- or poly-substituted with R ⁹ ), tri (C ₁ to C ₆ alkyl) silyloxy. It represents a group or a cyano group, and the two ^R5s may be combined to form an oxo group (= O), or a C1 to C6 _alkoxyimino group, and the _two ^R5s are bound to each other. Select from a 3- to 6-membered carbocycle, or a nitrogen atom, an oxygen atom, and a sulfur atom (the sulfur atom may be substituted with one or two oxo groups (= O)) together with these bonded carbon atoms. It may form a 3- to 6-membered heterocycle having 1 to 4 heteroatoms to be formed.
R ⁶ is a hydrogen atom, C ₁ to C ₆ alkyl group, C ₂ to C ₆ alkenyl group, C ₂ to C ₆ alkynyl group, C ₁ to C ₆ haloalkyl group, C ₃ to C ₆ cycloalkyl group, C ₃ ~ C ₆ halocycloalkyl group, C ₃ ~ C ₆ cycloalkyl C ₁ ~ C ₆ alkyl group, C ₁ ~ C ₆ alkoxy C ₁ ~ C ₆ alkyl group, C ₁ ~ C ₆ haloalkoxy C ₁ ~ C ₆ alkyl Group, cyano C ₁ to C ₆ alkyl group, C ₁ to C ₆ alkyl carbonyl group, C ₁ to C ₆ alkoxycarbonyl group or C ₁ to C ₆ alkyl sulfonyl group.
R ⁷ is a halogen atom, C ₁ to C ₆ alkyl group, C ₂ to C ₆ alkenyl group, C ₂ to C ₆ alkynyl group, C ₁ to C ₆ haloalkyl group, C ₃ to C ₆ cycloalkyl group, C ₃ ~ C ₆ halocycloalkyl group, hydroxy group, C ₁ ~ C ₆ alkoxy group, C ₁ ~ C ₆ haloalkoxy group, C ₁ ~ C ₆ alkylthio group, C ₁ ~ C ₆ alkyl sulfinyl group, C ₁ ~ C ₆ Indicates an alkylsulfonyl group, _a C1 to C6 _{haloalkylthio} group, _a C1 to C6 _{haloalkylsulfinyl} group, _a C1 to C6 _{haloalkylsulfonyl} group, a cyano group or a nitro group.
Z represents an oxygen atom or a sulfur atom.
A indicates N or CR ¹³ .
R ¹³ represents a hydrogen atom, a halogen atom or a cyano group]
Condensed heterocyclic derivative represented by, or an agriculturally acceptable salt thereof.

(2) In the general formula [I], R ¹ is a hydrogen atom, a C ₁ to C ₆ alkyl group (the group may be mono-substituted or poly-substituted by R ⁸ ), a C ₂ -C ₆ alkenyl group (the group may be mono-substituted or poly-substituted by R 8). The group may be mono-substituted or poly-substituted with R ⁸ ), a _C2 _- C6 alkynyl group (the group may be mono- or poly-substituted with R ⁸ ), a phenyl group (the group may be R ⁹ ). ( ^May be mono-substituted or poly-substituted by R9) or a heteroaryl group (the group may be mono- or poly-substituted by R9).
R ⁸ is a halogen atom, C ₁ to C ₆ haloalkyl group, C ₃ to C ₆ cycloalkyl group, C ₃ to C ₆ halocycloalkyl group, benzoyl group (the group is mono-substituted or poly-substituted by R ⁹ ). C ₁ to C ₆ alkoxycarbonyl group, C ₁ to C ₆ alkoxy group, C ₁ to C ₆ haloalkoxy group, C ₃ to C ₆ cycloalkoxy group, C ₃ to C ₆ halocycloalkoxy group, C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkoxy group, phenoxy group (the group may be mono-substituted or poly-substituted with R ⁹ ), C ₁ to C ₆ haloalkyl thio group, C ₁ to C ₆ haloalkyl sulfinyl. Group, C ₁ to C ₆ haloalkylsulfonyl group, phenylthio group (the group may be mono-substituted or poly-substituted with R ⁹ ), phenylsulfinyl group (the group may be mono-substituted or poly-substituted with R ⁹ ). ), Phenylsulfonyl group (the group may be mono-substituted or poly-substituted with R ⁹ ), phenylsulfonyl amino group (the phenyl group may be mono-substituted or poly-substituted with R ⁹ ), the amino group may be R (May be substituted with ¹² ), phenyl group (the group may be mono-substituted or poly-substituted with R ⁹ ), heteroaryl group (the group may be mono- or poly-substituted with R ⁹ ),. A heteroaryloxy group (the group may be mono-substituted or poly-substituted with R ⁹ ), a heterocycloalkyl group (the group may be mono-substituted or poly-substituted with R ⁹ ), a cyano group or a thiocyanato group. Show,
R ⁹ represents a halogen atom, a C ₁ to C ₆ alkyl group, a C ₁ to C ₆ haloalkyl group, a formyl group, a C ₁ to C ₆ alkoxy group, a C ₁ to C ₆ haloalkoxy group, a cyano group or a nitro group. ,
R ¹⁰ indicates a hydrogen atom and represents a hydrogen atom.
R ¹¹ represents a C ₁ to C ₆ alkyl group.
R ¹² represents a C ₁ to C ₆ alkyl group.
R ² represents a hydrogen atom, a C ₁ to C ₆ alkyl group, a C ₁ to C ₆ haloalkyl group, a C ₁ to C ₆ alkoxycarbonyl group, an aminocarbonyl group or a cyano group.
R ³ is a hydrogen atom, a halogen atom, a C ₁ to C ₆ alkyl group, a C ₂ to C ₆ alkenyl group, a C ₁ to C ₆ haloalkyl group, a C ₃ to C ₆ cycloalkyl group, and a C ₁ to C ₆ alkoxy C. ₁ to C ₆ alkyl groups, C ₁ to C ₆ alkylthio C ₁ to C ₆ alkyl groups, C ₁ to C ₆ alkyl sulfinyl C ₁ to C ₆ alkyl groups, C ₁ to C ₆ alkyl sulfonyl C ₁ to C ₆ alkyl groups , C ₁ to C ₆ haloalkylthio C ₁ to C ₆ alkyl groups, C ₁ to C ₆ haloalkylsulfinyl C ₁ to C ₆ alkyl groups, C ₁ to C ₆ haloalkylsulfonyl groups ₁ to C ₆ alkyl groups, formyl groups,- C (R ¹⁰ ) = NOR ¹¹ , aminocarbonyl group, C ₁ to C ₆ alkoxy group, C ₁ to C ₆ haloalkoxy group, heteroaryloxy group (the group may be mono-substituted or poly-substituted by R ⁹ ). ), C ₁ to C ₆ alkylthio groups, C ₁ to C ₆ alkyl sulfinyl groups, C ₁ to C ₆ alkyl sulfonyl groups, C ₁ to C ₆ alkyl amino groups (the amino groups may be substituted with R ¹² ). , A phenyl group (the group may be mono- or poly-substituted by ^R9 ) or a cyano group.
R ⁴ represents a halogen atom or a C ₁ to C ₆ alkyl group.
m represents an integer of 0 or 1 and represents
Y represents an oxygen atom or a sulfur atom.
R ⁵ is independently a halogen atom, C ₁ to C ₆ alkyl group, C ₁ to C ₆ haloalkyl group, hydroxy group, C ₁ to C ₆ alkoxy group, C ₁ to C ₆ halo alkoxy group, heteroaryloxy group. (The group may be mono-substituted or poly-substituted with R ⁹ ) or a tri (C ₁ to C ₆ alkyl) silyloxy group, and the two R ^5s together are an oxo group (= O), or C ₁ to C ₆ alkoxyimino groups may be formed, and the two R ^5s may be bonded to each other to form a 3- to 6-membered carbon ring together with these bonded carbon atoms, or a nitrogen atom, an oxygen atom and a sulfur atom. A 3- to 6-membered heterocycle having 1 to 4 heteroatoms selected from (the sulfur atom may be substituted with 1 or 2 oxo groups (= O)) may be formed.
R ⁶ represents a C ₁ to C ₆ alkyl group or a C ₁ to C ₆ haloalkyl group.
R ⁷ represents _a halogen atom, a C1 to _C6 haloalkyl group or a cyano group.
Z is the condensed heterocyclic derivative according to (1) above, which represents an oxygen atom, or an agriculturally acceptable salt thereof.

(3) In the general formula [I], Q represents Q-1, Q-2, Q-3 or Q-4.
R ¹ represents a C ₁ to C ₆ alkyl group (the group may be mono- or poly-substituted by R ⁸ ).
R ⁸ is a C ₃ to C ₆ cycloalkyl group, a C ₃ to C ₆ halocycloalkyl group, a benzoyl group (the group may be mono-substituted or poly-substituted by R ⁹ ), C ₁ to C ₆ alkoxycarbonyl. Group, C ₃ to C ₆ cycloalkoxy group, C ₃ to C ₆ halocycloalkoxy group, C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkoxy group, phenoxy group (the group is mono-substituted or poly-substituted by R ⁹ ). _C ₁ to _C ₆ haloalkylthio groups, C1 to _C6 haloalkylsulfinyl groups, C1 to _C6 haloalkylsulfonyl groups, ^phenylthio groups (the groups may be mono-substituted or poly-substituted by R9). (Good), phenylsulfinyl group (the group may be mono-substituted or poly-substituted with R ⁹ ), phenylsulfonyl group (the group may be mono- or poly-substituted with R ⁹ ), phenylsulfonylamino group (may be). The phenyl group may be mono-substituted or poly-substituted with R ⁹ , the amino group may be substituted with R ¹² ), a phenyl group (the group may be mono- or poly-substituted with R ⁹ ). , Heteroaryl group (the group may be mono-substituted or poly-substituted with R ⁹ ), heteroaryloxy group (the group may be mono-substituted or poly-substituted with R ⁹ ), heterocycloalkyl group (the group may be mono-substituted or poly-substituted). The group may be mono-substituted or poly-substituted with R9), the fused heterocyclic derivative according to ( ² ) above, which exhibits a cyano group or a thiocyanato group, or an agriculturally acceptable salt thereof.

(4) In the general formula [I], R ⁸ is a phenyl group (the group may be mono-substituted or poly-substituted by R ⁹ ), a heteroaryl group (the group may be mono-substituted or poly-substituted by R ⁹ ). The fused heterocyclic derivative according to (3) above, or an agriculturally acceptable salt thereof, which indicates (may be).

(5) In the general formula [I], Q is the condensed heterocyclic derivative according to (3) above, which represents Q-1, or an agriculturally acceptable salt thereof.

(6) In the general formula [I], Q is the condensed heterocyclic derivative according to (3) or (4) above, which represents Q-2, or an agriculturally acceptable salt thereof.

(7) In the general formula [I], Q is the condensed heterocyclic derivative according to (3) or (4) above, which represents Q-3, or an agriculturally acceptable salt thereof.

(8) In the general formula [I], Q is the condensed heterocyclic derivative according to (3) above, which represents Q-4, or an agriculturally acceptable salt thereof.

(9) In the general formula [I], Q is the condensed heterocyclic derivative according to (1) or (2) above, which represents Q-5, Q-6, Q-7 or Q-8, or its agriculture. Above acceptable salt.

(10) In the general formula [I], Q is the condensed heterocyclic derivative according to (1) or (2) above, which represents Q-5, or an agriculturally acceptable salt thereof.

(11) In the general formula [I], Q is the condensed heterocyclic derivative according to (1) or (2) above, which represents Q-6, or an agriculturally acceptable salt thereof.

(12) In the general formula [I], Q is the condensed heterocyclic derivative according to (1) or (2) above, which represents Q-7, or an agriculturally acceptable salt thereof.

(13) In the general formula [I], Q is the condensed heterocyclic derivative according to (1) above, which is represented by Q-8, or an agriculturally acceptable salt thereof.

(14) A pesticide composition containing the condensed heterocyclic derivative according to any one of (1) to (13) above, or an agriculturally acceptable salt thereof as an active ingredient.

(15) The pesticide composition according to (14) above, which further contains a surfactant.

(16) A herbicide containing the condensed heterocyclic derivative according to any one of (1) to (13) above, or an agriculturally acceptable salt thereof as an active ingredient.

(17) For weeds growing in fields, paddy fields, orchards, turf, non-agricultural land, greenhouses, nursery facilities, or plant factories that cultivate useful plants for agricultural, horticultural, and industrial purposes. , The herbicide according to (16) above, which has a herbicidal effect.

(18) The herbicide according to (17) above, wherein the useful plant having agricultural, horticultural and industrial uses is a trait plant in cultivation by a breeding method or a gene recombination technique.

The condensed heterocyclic derivative represented by the general formula [I] of the present invention or an agriculturally acceptable salt thereof can control various weeds generated in upland fields, paddy fields, orchards, and non-agricultural lands, and is more useful. It has excellent action and effect as a pesticide, such as showing high safety to plants and the like.

The symbols and terms described in this specification will be explained.

In the present invention, the "halogen atom" refers to a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

In the present invention, notations such as "C ₁ to C ₆ " indicate that the number of carbon atoms of the subsequent substituent is 1 to 6 in this case.

In the present invention, the "C ₁ to C ₆ alkyl group" refers to a linear or branched alkyl group having 1 to 6 carbon atoms, unless otherwise specified, for example, methyl, ethyl, n-propyl, and the like. Isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl , Neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl- Groups such as 1-methylpropyl or 1-ethyl-2-methylpropyl can be mentioned.

In the present invention, the " _C2 to C6 alkenyl group" refers to a linear or branched alkenyl group having 2 to ₆ carbon atoms, and is, for example, vinyl, 1-propenyl, isopropenyl, for example, unless otherwise specified. , 2-propenyl, 1-butenyl, 1-methyl-1-propenyl, 2-butenyl, 1-methyl-2-propenyl, 3-butenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, 1 , 3-Butadienyl, 1-pentenyl, 1-ethyl-2-propenyl, 2-pentenyl, 1-methyl-1-butenyl, 3-pentenyl, 1-methyl-2-butenyl, 4-pentenyl, 1-methyl-3 -Butenyl, 3-methyl-1-butenyl, 1,2-dimethyl-2-propenyl, 1,1-dimethyl-2-propenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1,2 -Dimethyl-1-propenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,3-pentadienyl, 1-vinyl-2-propenyl, 1-hexenyl, 1-propyl-2-propenyl, 2 -Hexenyl, 1-methyl-1-pentenyl, 1-ethyl-2-butenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-4-pentenyl, 1-ethyl-3-butenyl, 1- (Isobutyl) Vinyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-2-propenyl, 1- (isopropyl) -2-propenyl, 2-methyl-2-pentenyl, 3-methyl -3-pentenyl, 4-methyl-3-pentenyl, 1,3-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1 , 2-Dimethyl-3-butenyl, 1,3-dimethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1,5-hexadienyl, 1-vinyl-3-butenyl or 2,4-hexadienyl Etc. can be mentioned.

In the present invention, the " _C2 to C6 alkynyl group" refers to a linear or branched alkynyl group having 2 to ₆ carbon atoms, unless otherwise specified, for example, ethynyl, 1-propynyl, 2-. Propinyl, 1-butynyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 1-ethyl-2-propynyl, 2-pentynyl, 3-pentynyl, 1-methyl-2-butynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-hexynyl, 1- (n-propyl) -2-propynyl, 2-hexynyl, 1-ethyl-2-butynyl, 3- Hexinyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 4-methyl-1-pentynyl, 3-methyl-1-pentynyl, 5-hexynyl, 1-ethyl-3-butynyl, 1-ethyl- Groups such as 1-methyl-2-propynyl, 1- (isopropyl) -2-propinyl, 1,1-dimethyl-2-butynyl or 2,2-dimethyl-3-butynyl can be mentioned.

In the present invention, the "C ₃ to C ₆ cycloalkyl group" refers to a cycloalkyl group having 3 to 6 carbon atoms unless otherwise specified, and examples thereof include groups such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. be able to.

In the present invention, the "heteroaryl group" is a 5-membered or 6-membered single having 1 to 6 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom in addition to a carbon atom, unless otherwise specified. It shows a ring heterocycle, for example, thiophen-2-yl, thiophen-3-yl, furan-2-yl, furan-3-yl, pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, Oxazole-2-yl, Oxazole-4-yl, Oxazole-5-yl, Isoxazole-3-yl, Isoxazole-4-yl, Isoxazole-5-yl, Thiazole-2-yl, Thiazole-4-yl , Thiazole-5-yl, isothiazole-3-yl, isothiazole-4-yl, isothiazole-5-yl, imidazole-1-yl, imidazole-2-yl, imidazole-4-yl, pyrazole-1- Il, pyrazole-3-yl, pyrazole-4-yl, pyrazole-5-yl, 1,3,4-oxadiazole-2-yl, 1,2,3-oxadiazole-4-yl, 1, 2,3-oxadiazole-5-yl, 1,2,4-oxadiazole-3-yl, 1,2,4-oxadiazole-5-yl, 1,2,5-oxadiazole- 3-yl, 1,3,4-thiazole-2-yl, 1,2,3-thiazole-4-yl, 1,2,3-thiazole-5-yl, 1,2,4-thiazole-3- Ill, 1,2,4-thiazole-5-yl, 1,2,5-thiazole-3-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-1-yl, 1,2,3-Triazole-1-yl, 1,2,3-triazole-2-yl, 1,3,4-triazole-1-yl, tetrazole-1-yl, tetrazole-2-yl, tetrazole- 5-yl, pyridine-2-yl, pyridine-3-yl, pyridine-4-yl, pyrimidine-2-yl, pyrimidine-4-yl, pyrimidine-5-yl, pyridazine-3-yl, pyridazine-4- Groups such as yl, pyrazine-2-yl, 1,3,5-triazinin-2-yl and the like can be mentioned.

In the present invention, "C ₁ to C ₆ haloalkyl groups" refers to linear or branched alkyl groups having 1 to 6 carbon atoms substituted with the same or different halogen atoms 1 to 13 unless otherwise specified. Shown, eg, haloalkyl groups, eg, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, iodomethyl, chlorodifluoromethyl, dichlorofluoromethyl, 1 -Fluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 1 -Chloroethyl, 2-chloroethyl, 1,1-dichloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 1,1,2,2-tetrachloroethyl, pentachloroethyl, 1-bromoethyl, 2 -Bromoethyl, 2,2,2-tribromoethyl, 1-iodoethyl, 2-iodoethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 1-fluoropropyl, 2- Fluoropropyl, 3-fluoropropyl, 1,1-difluoropropyl, 2,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, 2,2,3,3,3-penta Fluoropropyl, 1,1,2,3,3,3-hexafluoropropyl, heptafluoropropyl, 1-fluoropropane-2-yl, 2-fluoropropane-2-yl, 1,1-difluoropropane-2-yl Il, 1,2-difluoropropane-2-yl, 1,3-difluoropropane-2-yl, 1,2,3-trifluoropropane-2-yl, 1,1,3,3-tetrafluoropropane- 2-yl, 1,1,1,3,3,3-hexafluoropropane-2-yl, heptafluoropropane-2-yl, 1-chloropropyl, 2-chloropropyl, 3-chloropropyl, 1,1 -Dichloropropyl, 2,2-dichloropropyl, 3,3-dichloropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentachloropropyl, heptachloropropyl, 1-chloropropane-2 -Il, 2-chloropropane-2-yl, 1,1-dichloropropane-2-yl, 1,2-dichloropropane-2-yl, 1,3- Dichloropropane-2-yl, 1,2,3-trichloropropane-2-yl, 1,1,3,3-tetrachloropropane-2-yl, 1,1,1,3,3,3-hexachloropropane- 2-yl, heptachloropropane-2-yl, 1-bromopropyl, 2-bromopropyl, 3-bromopropyl, 1-bromopropane-2-yl, 2-bromopropane-2-yl, 1-iodopropyl, 2 -Iodopropyl, 3-iodopropyl, 1-iodopropane-2-yl, 2-iodopropane-2-yl, 1-fluorobutyl, 2-fluorobutyl, 3-fluorobutyl, 4-fluorobutyl, 4,4 -Difluorobutyl, 4,4,4-trifluorobutyl, 4,4,4-trifluoro-3-methylbutyl, 3,3,4,4,4-pentafluorobutyl, 2,2,3,4,4 , 4-Hexafluorobutyl, 2,2,3,3,4,4,4-heptafluorobutyl, nonafluorobutyl, 1,1,1-trifluorobutane-2-yl, 4,4,4-tri Fluorobutane-2-yl, 3,3,4,4,4-pentafluorobutane-2-yl, nonafluorobutane-2-yl, 1,1,1,3,3,3-hexafluoro-2-yl (Trifluoromethyl) Propane-2-yl, 3,4,4,4-tetrafluoro-3- (trifluoromethyl) butyl, 1-chlorobutyl, 2-chlorobutyl, 3-chlorobutyl, 4-chlorobutyl, 4,4 -Dichlorobutyl, 4,4,4-trichlorobutyl, nonachlorobutyl, 1,1,1-trichlorobutane-2-yl, 4,4,4-trichlorobutane-2-yl, nonachlorobutane-2-yl, 1 -Bromobutyl, 2-bromobutyl, 3-bromobutyl, 4-bromobutyl, 1-iodobutyl, 2-iodobutyl, 3-iodobutyl, 4-iodobutyl, 4-chloro-1,1,2,2,3,3,4,4 -Octafluorobutyl, 4-bromo-1,1,2,2,3,3,4,4-octafluorobutyl, 1-fluoropentyl, 2-fluoropentyl, 3-fluoropentyl, 4-fluoropentyl, 5 -Fluoropentyl, 5,5-difluoropentyl, 5,5,5-trifluoropentyl, 4,4,5,5,5-pentafluoropentyl, 3,3,4,5,5,5-hepta Fluoropentyl, 2,2,3,3,4,5,5-octafluoropentyl, 2,2,3,3,4,5,5,5-nonaflu Oropentil, Undecafluoropentyl, 1-chloropentyl, 2-chloropentyl, 3-chloropentyl, 4-chloropentyl, 5-chloropentyl, 5,5,5-trichloropentyl, 4,4,5,5,5 -Pentachloropentyl, 3,3,4,5,5,5-heptachloropentyl, 2,2,3,3,4,5,5,5-nonachloropentyl, undecachloropentyl, 1-bromopentyl, 2-bromopentyl, 3-bromopentyl, 4-bromopentyl, 5-bromopentyl, 5-iodopentyl, 1-fluorohexyl, 2-fluorohexyl, 3-fluorohexyl, 4-fluorohexyl, 5-Fluorohexyl, 6-Fluorohexyl, 6,6,6-trifluorohexyl, 5,5,6,6,6-pentafluorohexyl, 4,4,5,5,6,6-Heptafluoro Hexil, 3,3,4,4,5,5,6,6,6-nonafluorohexyl, 2,2,3,3,4,4,5,6,6,6-undecafluorohexyl , 2,2,3,3,4,5,5,6-decafluorohexyl, tridecafluorohexyl, 1-chlorohexyl, 2-chlorohexyl, 3-chlorohexyl, 4-chlorohexyl, Groups such as 5-chlorohexyl, 6-chlorohexyl, 5-bromohexyl, 6-bromohexyl, 5-iodohexyl or 6-iodohexyl can be mentioned.

In the present invention, "C ₃ to C ₆ halocycloalkyl group" refers to a cycloalkyl group having 3 to 6 carbon atoms substituted with the same or different halogen atoms of 1 to 11 unless otherwise specified. , For example, 1-fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl, 1-chlorocyclopropyl, 2-chlorocyclopropyl, 2, 2-Dichlorocyclopropyl, 2,2,3,3-tetrachlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-diiodocyclopropyl, 1-fluorocyclobutyl, 2-fluorocyclobutyl, 3- Fluorocyclobutyl, 3,3-difluorocyclobutyl, heptafluorocyclobutyl, 2-chlorocyclobutyl, 3-chlorocyclobutyl, 3,3-dichlorocyclobutyl, 3,3-dibromocyclobutyl, 3,3-di Iodocyclobutyl, 1-fluorocyclopentyl, 2-fluorocyclopentyl, 3-fluorocyclopentyl, 2,2-difluorocyclopentyl, 3,3-difluorocyclopentyl, nonafluorocyclopentyl, 2,2-dichlorocyclopentyl, 3,3-dichlorocyclopentyl , 2,2-Dibromocyclopentyl, 3,3-dibromocyclopentyl, 2,2-diiodocyclopentyl, 3,3-diiodocyclopentyl, 1-fluorocyclohexyl, 2-fluorocyclohexyl, 3-fluorocyclohexyl, 4-fluorocyclohexyl , 2,2-Difluorocyclohexyl, 3,3-difluorocyclohexyl, 4,4-difluorocyclohexyl, 1-chlorocyclohexyl, 2-chlorocyclohexyl, 3-chlorocyclohexyl, 4-chlorocyclohexyl, 2,2-dichlorocyclohexyl, 3 , 3-Dichlorocyclohexyl, 4,4-dichlorocyclohexyl, 3,3-dibromocyclohexyl, 4,4-dibromocyclohexyl, 3,3-diiodocyclohexyl, 4,4-diiodocyclohexyl and the like. ..

In the present invention, the "C ₁ to C ₆ alkylcarbonyl group" means, unless otherwise specified, an alkyl moiety having the above meaning (C ₁ to C ₆ alkyl) -C (= O) -group, for example. , Acetyl, propionyl, 2-methylpropionyl, 2,2-dimethylpropionyl, butanoyl, 2-methylbutanoyl, 3-methylbutanoyl, 2-ethylbutanoyl, 2,2-dimethylbutanoyl, 2,3-dimethyl Groups such as butanoyl, 3,3-dimethylbutanoyl, pentanoyl, 2-methylpentanoyl, 3-methylpentanoyl, 4-methylpentanoyl or hexanoyl can be mentioned.

In the present invention, the "C ₁ to C ₆ haloalkylcarbonyl group" means, unless otherwise specified, the haloalkyl moiety has the above meaning (C ₁ to C ₆ haloalkyl) -C (= O) -group, for example. , Fluoroacetyl, difluoroacetyl, trifluoroacetyl, chloroacetyl, trichloroacetyl, tribromoacetyl, 3,3,3-trifluoropropionyl, 3,3-difluoropropionyl or 4,4,4-trifluorobutyryl, etc. The group can be mentioned.

In the present invention, the "C ₃ to C ₆ cycloalkylcarbonyl group" means the above-mentioned meaning of the cycloalkyl moiety unless otherwise specified (C ₃ to C ₆ cycloalkyl) -C (= O) -group. Examples thereof include groups such as cyclopropanecarbonyl, cyclobutanecarbonyl, cyclopentanecarbonyl, cyclohexanecarbonyl and the like.

In the present invention, the "C ₁ to C ₆ alkoxycarbonyl group" means, unless otherwise specified, the alkoxy moiety has the above meaning (C ₁ to C ₆ alkoxy) -C (= O) -group, for example. , Methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methyl Groups such as butoxycarbonyl, 3-methylbutoxycarbonyl, 1-ethylpropoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl or 2,2-dimethylpropoxycarbonyl can be mentioned.

In the present invention, the "C ₁ to C ₆ haloalkoxycarbonyl group" means the above-mentioned meaning of the haloalkyl moiety unless otherwise specified (C ₁ to C ₆ haloalkyl) -OC (= O) -group. Shown are 2-fluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, pentafluoroethoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl or heptafluoro-2- Groups such as propoxycarbonyl can be mentioned.

In the present invention, the "C ₁ to C ₆ alkylaminocarbonyl group" means the above-mentioned meaning of the alkyl moiety unless otherwise specified (C ₁ to C ₆ alkyl) -NH-C (= O) -group. Shown, for example, methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, n-butylaminocarbonyl, isobutylaminocarbonyl, sec-butylaminocarbonyl, tert-butylaminocarbonyl, n-pentylaminocarbonyl, 1-Methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 1-ethylpropylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl, 2,2- Groups such as dimethylpropylaminocarbonyl or n-hexylaminocarbonyl can be mentioned.

In the present invention, the "C ₁ to C ₆ haloalkylaminocarbonyl group" means the above-mentioned meaning of the haloalkyl moiety unless otherwise specified (C ₁ to C ₆ haloalkyl) -NH-C (= O) -group. Shown, for example, 2-fluoroethylaminocarbonyl, 2,2-difluoroethylaminocarbonyl, 2,2,2-trifluoroethylaminocarbonyl, 2,2,2-trichloroethylaminocarbonyl, pentafluoroethylaminocarbonyl or 1 , 1,1,3,3,3-hexafluoro-2-propylaminocarbonyl and the like can be mentioned.

In the present invention, the "C ₁ to C ₆ alkoxy group" means an (C ₁ to C ₆ alkyl) -O- group in which the alkyl moiety has the above meaning unless otherwise specified, and for example, methoxy, ethoxy, etc. n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1-ethylpropoxy, 1,1-dimethyl Groups such as propoxy, 1,2-dimethylpropoxy or n-hexyloxy can be mentioned.

In the present invention, "C ₃ to C ₆ alkenyloxy group" means an (C ₃ to C ₆ alkenyl) -O- group in which the alkenyl moiety has the above meaning unless otherwise specified, and for example, 2-propenyl. Oxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 2-butenyloxy, 3-butenyloxy, 3-methyl-2-butenyloxy, 4-methyl-3-butenyloxy, 4-pentenyloxy or 5 -A group such as hexenyloxy can be mentioned.

In the present invention, the "C ₃ to C ₆ alkynyloxy group" means an (C ₃ to C ₆ alkynyl) -O- group in which the alkynyl moiety has the above meaning unless otherwise specified, and for example, 2-propynyl. Oxy, 1-methyl-2-propynyloxy, 1-ethyl-2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-butynyloxy, 2-pentynyloxy, 4-pentynyloxy or 4, Groups such as 4-dimethyl-2-pentynyloxy can be mentioned.

In the present invention, "C ₁ to C ₆ haloalkoxy group" means an (C ₁ to C ₆ haloalkyl) -O- group in which the haloalkyl moiety has the above meaning unless otherwise specified, and for example, difluoromethoxy, etc. Dichloromethoxy, trifluoromethoxy, trichloromethoxy, tribromomethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 1-chloroethoxy, 2-chloroethoxy, 1-bromoethoxy, 2-bromoethoxy, 2,2 -Difluoroethoxy, 1,2-dichloroethoxy, 2,2-dichloroethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxy, 1,1,2,2-tetrafluoroethoxy, penta Fluoroethoxy, 2-bromo-2-chloroethoxy, 2-chloro-1,1,2,2-tetrafluoroethoxy, 1-chloro-1,2,2,2-tetrafluoroethoxy, 1-chloropropoxy, 2 -Chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2-bromo-1-methylethoxy, 3-iodopropoxy, 2,3-dichloropropoxy, 2,3-dibromopropoxy, 3,3 , 3-Trifluoropropoxy, 3,3,3-trifluoro-2-propoxy, 3,3,3-trichloropropoxy, 3-bromo-3,3-difluoropropoxy, 2,2-difluoropropoxy, 3,3 -Dichloro-3-fluoropropoxy, 2,2,3,3-tetrafluoropropoxy, 1-bromo-3,3,3-trifluoropropoxy, 2,2,3,3,3-pentafluoropropoxy, 2, 2,2-Trifluoro-1-trifluoromethylethoxy, heptafluoropropoxy, heptafluoro-2-propoxy, 1,2,2,2-tetrafluoro-1-trifluoromethylethoxy, 1,1,2,3 , 3,3-Hexafluoropropoxy, 2-chlorobutoxy, 3-chlorobutoxy, 4-chlorobutoxy, 2-chloro-1,1-dimethylethoxy, 4-bromobutoxy, 3-bromo-2-methylpropoxy, 2 -Bromo-1,1-dimethylethoxy, 2,2-dichloro-1,1-dimethylethoxy, 2-chloro-1-chloromethyl-2-methylethoxy, 4,4,4-trifluorobutoxy, 3,3 , 3-Trifluoro-1-methylpropoxy, 3,3,3-trifluoro-2-methylpropoxy, 2,3 , 4-Trichlorobutoxy, 2,2,2-trichloro-1,1-dimethylethoxy, 4-chloro-4,4-difluorobutoxy, 4,4-dichloro-4-fluorobutoxy, 4-bromo-4,4 -Difluorobutoxy, 2,4-dibromo-4,4-difluorobutoxy, 3,4-dichloro-3,4,4-trifluorobutoxy, 3,3-dichloro-4,4,4-trifluorobutoxy, 4 -Bromo-3,3,4,4-tetrafluorobutoxy, 4-bromo-3-chloro-3,4,54-trifluorobutoxy, 2,2,3,3,4,4-hexafluorobutoxy, 2 , 2,3,4,4,4-hexafluorobutoxy, 2,2,2-trifluoro-1-methyl-1-trifluoromethylethoxy, 3,3,3-trifluoro-2-trifluoromethylpropoxy , 2,2,3,3,4,5,4-heptafluorobutoxy, 3,3,4,4,4-pentafluoro-2-butoxy, 2,3,3,3-tetrafluoro-2-tri Fluoromethylpropoxy, 1,1,2,2,3,3,4,4-octafluorobutoxy, nonafluorobutoxy, perfluoro-tert-butoxy, 4-chloro-1,1,2,2,3,3 , 4,4-octafluorobutoxy, 5,5,5-trifluoropentoxy, 4,4,5,5,5-pentafluoropentoxy, 3,3,4,5,4,5,5-hepta Fluoropentoxy, 3,3,4,4,5,5,5-heptafluoro-2-pentoxy, 2,2,3,3,4,5,5-, nonafluoropentoxy, 2, 2,3,3,4,5,5-octafluoropentoxy, perfluoropentoxy, 4,4,5,5,5-pentafluoro-2-butoxy, 2,2-bis (triflulomethyl) ) Propoxy, 2,2,3,3,4,5,5,5,6,6-Undecafluorohexyloxy, 3,3,4,4,5,5,6,6,6-Nona Fluorohexyloxy, 4,4,5,5,6,6,6-heptafluorohexyloxy, 2,2,3,3,4,5,5,6,6-decafluorohexyloxy, 4, Groups such as 4,4-trifluoro-3,3-bis (trifluoromethyl) butyloxy or perfluorohexyloxy can be mentioned.

In the present invention, "C ₃ to C ₆ cycloalkoxy group" means an (C ₃ to C ₆ cycloalkyl) -O- group in which the cycloalkyl moiety has the above meaning unless otherwise specified, and for example, cyclo. Groups such as propoxy, cyclobutoxy, cyclopentyloxy or cyclohexyloxy can be mentioned.

In the present invention, the "C ₃ to C ₆ halocycloalkoxy group" indicates a (C ₃ to C ₆ halocycloalkyl) -O- group in which the halocycloalkyl moiety has the above meaning unless otherwise specified. For example, 2,2-difluorocyclopropoxy, 2,2-dichlorocyclopropoxy, 3,3-difluorocyclobutoxy, 3,3-dichlorocyclobutoxy, 3-fluorocyclopentyloxy, 3,3-difluorocyclopentyloxy, nonafluoro. Groups such as cyclopentyloxy, 3,3-dichlorocyclopentyloxy, 4,4-difluorocyclohexyloxy or 4,4-dichlorocyclohexyloxy can be mentioned.

In the present invention, "C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkoxy group" means the cycloalkyl moiety as described above (C ₃ to C ₆ cycloalkyl)-(C ₁ ) unless otherwise specified. ~ C ₆ alkyl) -O-group, and examples thereof include groups such as cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, 2-cyclopropylethoxy, 2-cyclobutylethoxy or 2-cyclopentylethoxy.

In the present invention, "C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkoxy group" means the above-mentioned meaning of the halocycloalkyl moiety unless otherwise specified (C ₃ to C ₆ halocycloalkyl). It shows (C ₁ to C ₆ alkyl) -O- groups and indicates, for example, (1-fluorocyclopropyl) methoxy, (2-fluorocyclopropyl) methoxy, (2,2-difluorocyclopropyl) methoxy, (2-chloro). Groups such as cyclopropyl) methoxy or (2,2-dichlorocyclopropyl) methoxy can be mentioned.

In the present invention, the "phenyl C ₁ to C ₆ alkoxy group" refers to a phenyl- (C ₁ to C ₆ alkyl) -O- group in which the alkyl moiety has the above meaning, unless otherwise specified, for example, phenyl. Groups such as methoxy, 1-phenylethoxy, 2-phenylethoxy, 1-phenylpropoxy, 2-phenylbutoxy or 1-phenylpentoxy can be mentioned.

In the present invention, "C ₁ to C ₆ alkylthio group" means an (C ₁ to C ₆ alkyl) -S- group in which the alkyl moiety has the above meaning unless otherwise specified, and for example, methylthio, ethylthio, and the like. Groups such as n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio can be mentioned.

_In the present invention, the "C1 to C6 alkylsulfinyl group" means, unless otherwise specified, the alkyl moiety has the above meaning (C1 to _C6 alkyl) _-S (= O) _-group , for example. , Methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl and the like.

In the present invention, the "C ₁ to C ₆ alkyl sulfonyl group" means (C ₁ to C ₆ alkyl) -S (= O) _2- group in which the alkyl moiety has the above meaning unless otherwise specified. For example, groups such as methyl sulfonyl, ethyl sulfonyl, n-propyl sulfonyl, isopropyl sulfonyl, n-butyl sulfonyl, isobutyl sulfonyl, sec-butyl sulfonyl or tert-butyl sulfonyl can be mentioned.

In the present invention, "C ₁ to C ₆ haloalkylthio group" means a (C ₁ to C ₆ haloalkyl) -S- group in which the haloalkyl moiety has the above meaning unless otherwise specified, and for example, fluoromethylthio. Difluoromethylthio, trifluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, pentafluoroethylthio, 2,2,2-trichloroethylthio, 3,3,3-trifluoropropylthio, 1,1 , 2,3,3,3-hexafluoropropyl, heptafluoropropylthio, 1,1,1,3,3,3-hexafluoropropane-2-ylthio, heptafluoropropane-2-ylthio or 4,4 Groups such as 4-trifluorobutylthio can be mentioned.

_In the present invention, "C1 to C6 haloalkylsulfinyl group" means, unless otherwise specified, the haloalkyl moiety has the above meaning (C1 to _C6 haloalkyl) _-S (= O) _-group , for example. , Difluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl, pentafluoroethylsulfinyl, 3,3,3-trifluoropropylsulfinyl , Heptafluoropropylsulfinyl, heptafluoro-2-propylsulfinyl and the like.

In the present invention, "C ₁ to C ₆ haloalkyl sulfonyl group" means (C ₁ to C ₆ haloalkyl) -S (= O) _2- group in which the haloalkyl moiety has the above meaning unless otherwise specified. For example, difluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, pentafluoroethylsulfonyl, 3,3,3-trifluoropropylsulfonyl, heptafluoropropylsulfonyl or heptafluoro- Groups such as 2-propylsulfonyl and the like can be mentioned.

In the present invention, "C ₃ to C ₆ cycloalkylthio group" means a (C ₃ to C ₆ cycloalkyl) -S- group in which the cycloalkyl moiety has the above meaning unless otherwise specified, and for example, cyclo. Groups such as propylthio, cyclobutylthio, cyclopentylthio or cyclohexylthio can be mentioned.

In the present invention, the "C ₃ to C ₆ cycloalkylsulfinyl group" means the above-mentioned meaning of the cycloalkyl moiety unless otherwise specified (C ₃ to C ₆ cycloalkyl) -S (= O) -group. Examples thereof include groups such as cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl or cyclohexylsulfinyl.

In the present invention, the "C ₃ to C ₆ cycloalkyl sulfonyl group" means the above-mentioned meaning of the cycloalkyl moiety unless otherwise specified (C ₃ to C ₆ cycloalkyl) -S (= O) ₂ -group. For example, a group such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, or cyclohexylsulfonyl can be mentioned.

In the present invention, "C ₃ to C ₆ halocycloalkylthio group" means a (C ₃ to C ₆ halocycloalkyl) -S- group in which the halocycloalkyl moiety has the above meaning unless otherwise specified. For example, groups such as 2,2-difluorocyclopropylthio, 2,2-dichlorocyclopropylthio, 3,3-difluorocyclobutylthio, 3,3-difluorocyclopentylthio or 4,4-difluorocyclohexylthio are mentioned. be able to.

In the present invention, "C ₃ to C ₆ halocycloalkylsulfinyl group" means the above-mentioned meaning of the halocycloalkyl moiety unless otherwise specified (C ₃ to C ₆ halocycloalkyl) -S (= O). -Indicating a group, for example 2,2-difluorocyclopropylsulfinyl, 2,2-dichlorocyclopropylsulfinyl, 3,3-difluorocyclobutylsulfinyl, 3,3-difluorocyclopentylsulfinyl or 4,4-difluorocyclohexyl Groups such as sulfinyl can be mentioned.

In the present invention, the "C ₃ to C ₆ halocycloalkylsulfonyl group" means the above-mentioned meaning of the halocycloalkyl moiety unless otherwise specified (C ₃ to C ₆ halocycloalkyl) -S (= O). Indicates a ₂ -group, eg, to 2,2-difluorocyclopropylsulfonyl, 2,2-dichlorocyclopropylsulfonyl, 3,3-difluorocyclobutylsulfonyl, 3,3-difluorocyclopentylsulfonyl or 4,4-difluorocyclo. Groups such as xylsulfonyl can be mentioned.

In the present invention, "C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkylthio groups" means the cycloalkyl moiety and the alkyl moiety as described above (C ₃ to C ₆ cycloalkyl) unless otherwise specified. (C ₁ to C ₆ alkyl) -S-groups, eg cyclopropylmethylthio, 2-cyclopropylethylthio, 3-cyclopropylpropylthio, 4-cyclopropylbutylthio, 5-cyclopropylpentylthio, cyclo. Groups such as butylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio and the like can be mentioned.

In the present invention, "C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkyl sulfinyl groups" means the cycloalkyl moiety and the alkyl moiety as described above (C ₃ to C ₆ cycloalkyl) unless otherwise specified. -(C ₁ to C ₆ alkyl) -S (= O) -group indicates, for example, (cyclopropylmethyl) sulfinyl, (cyclobutylmethyl) sulfinyl, (cyclopentylmethyl) sulfinyl, (2-cyclopropylethyl) sulfinyl. , (2-Cyclobutylethyl) sulfinyl or (2-cyclopentylethyl) sulfinyl and the like.

In the present invention, "C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkyl sulfonyl groups" means the cycloalkyl moiety and the alkyl moiety as described above (C ₃ to C ₆ cycloalkyl) unless otherwise specified. -(C ₁ to C ₆ alkyl) -S (= O) _2- Indicates a group, for example, (cyclopropylmethyl) sulfonyl, (cyclobutylmethyl) sulfonyl, (cyclopentylmethyl) sulfonyl, (2-cyclopropylethyl). Groups such as sulfonyl, (2-cyclobutylethyl) sulfonyl or (2-cyclopentylethyl) sulfonyl can be mentioned.

In the present invention, "C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkylthio groups" means the above-mentioned meanings of the halocycloalkyl moiety and the alkyl moiety unless otherwise specified (C ₃ to C ₆ halocyclo). Alkyl)-(C ₁ to C ₆ alkyl) -S- groups, for example 2,2-difluorocyclopropylmethylthio, 2,2-dichlorocyclopropylmethylthio, 2- (2,2-difluorocyclopropyl) ethylthio. , 2- (2,2-Dichlorocyclopropyl) ethylthio, 2,2-difluorocyclobutylmethylthio, 4,4-difluorocyclohexylmethylthio and the like can be mentioned.

In the present invention, "C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkyl sulfinyl groups" means the above-mentioned meanings of the halocycloalkyl moiety and the alkyl moiety (C ₃ to C ₆ halo) unless otherwise specified. Cycloalkyl)-(C ₁ to C ₆ alkyl) -S (= O) -group, eg, (1-fluorocyclopropyl) methylsulfinyl, (2-fluorocyclopropyl) methylsulfinyl, (2,2- Groups such as difluorocyclopropyl) methylsulfinyl, (2-chlorocyclopropyl) methylsulfinyl or (2,2-dichlorocyclopropyl) methylsulfinyl can be mentioned.

In the present invention, "C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkyl sulfonyl groups" means the above-mentioned meanings of the halocycloalkyl moiety and the alkyl moiety unless otherwise specified (C ₃ to C ₆ halo). Cycloalkyl)-(C ₁ to C ₆ alkyl) -S (= O) ₂ -represents groups such as (1-fluorocyclopropyl) methylsulfonyl, (2-fluorocyclopropyl) methylsulfonyl, (2,2). -Groups such as (difluorocyclopropyl) methylsulfonyl, (2-chlorocyclopropyl) methylsulfonyl or (2,2-dichlorocyclopropyl) methylsulfonyl can be mentioned.

In the present invention, the "C ₁ to C ₆ alkylamino group" means an (C ₁ to C ₆ alkyl) -NH- group in which the alkyl moiety has the above meaning unless otherwise specified, and for example, methylamino. Groups such as ethylamino, n-propylamino, isopropylamino and the like can be mentioned.

In the present invention, the "C ₁ to C ₆ haloalkylamino group" means a (C ₁ to C ₆ haloalkyl) -NH- group in which the haloalkyl moiety has the above meaning unless otherwise specified, and for example, 2-fluoro. Ethylamino, 2,2-difluoroethylamino, 2,2,2-trifluoroethylamino, 2,2,2-trichloroethylamino, pentafluoroethylamino, 3,3,3-trifluoropropylamino or 1, Groups such as 1,1,3,3,3-hexafluoro-2-propylamino and the like can be mentioned.

In the present invention, the "C ₁ to C ₆ alkylcarbonylamino group" means the above-mentioned meaning of the alkyl moiety unless otherwise specified (C ₁ to C ₆ alkyl) -C (= O) -NH- group. Examples thereof include groups such as acetylamino, propionylamino, butyrylamino or isobutyrylamino.

In the present invention, the "C ₁ to C ₆ haloalkylcarbonylamino group" means the above-mentioned meaning of the haloalkyl moiety unless otherwise specified (C ₁ to C ₆ haloalkyl) -C (= O) -NH- group. Shown, for example, fluoroacetylamino, difluoroacetylamino, trifluoroacetylamino, chloroacetylamino, trichloroacetylamino, tribromoacetylamino, 3,3,3-trifluoropropionylamino, pentafluoropropionylamino or 3,3- Groups such as difluoropropionylamino and the like can be mentioned.

In the present invention, "C ₃ to C ₆ cycloalkyl carbonylamino group" means the above-mentioned meaning of the cycloalkyl moiety unless otherwise specified (C ₃ to C ₆ cycloalkyl) -C (= O) -NH. -A group is shown, and examples thereof include groups such as cyclopropylcarbonylamino, cyclobutylcarbonylamino, cyclopentylcarbonylamino, and cyclohexylcarbonylamino.

In the present invention, the "C ₁ to C ₆ alkoxycarbonylamino group" means the above-mentioned meaning of the alkoxy moiety unless otherwise specified (C ₁ to C ₆ alkyloxy) -C (= O) -NH- group. Examples thereof include groups such as methoxycarbonylamino, ethoxycarbonylamino, isopropoxycarbonylamino, tert-butoxycarbonylamino or isobutoxycarbonylamino.

In the present invention, "C ₁ to C ₆ haloalkoxycarbonylamino group" means the above-mentioned meaning of the haloalkoxy moiety unless otherwise specified (C ₁ to C ₆ haloalkicoxy) -C (= O) -NH-. The group indicates, for example, 2-fluoroethoxycarbonylamino, 2,2,2-trifluoroethoxycarbonylamino, 2,2,2-trichloroethoxycarbonylamino, pentafluoroethoxycarbonylamino, 3,3,3-trifluoro. Groups such as propoxycarbonylamino or heptafluoro-2-propoxycarbonylamino can be mentioned.

In the present invention, the "C ₁ to C ₆ alkylaminocarbonylamino group" has the above-mentioned meaning of the alkyl moiety unless otherwise specified (C ₁ to C ₆ alkyl) -NH-C (= O) -NH. -A group is shown, and examples thereof include groups such as methylaminocarbonylamino, ethylaminocarbonylamino, n-propylaminocarbonylamino, isopropylaminocarbonylamino and tert-butylaminocarbonylamino.

In the present invention, the "C ₁ to C ₆ haloalkylaminocarbonylamino group" means the above-mentioned meaning of the haloalkyl moiety unless otherwise specified (C ₁ to C ₆ haloalkyl) -NH-C (= O) -NH. -Indicates a group, for example 2-fluoroethylaminocarbonylamino, 2,2,2-trifluoroethylaminocarbonylamino, 2,2,2-trichloroethylaminocarbonylamino, pentafluoroethylaminocarbonylamino or 1,1 , 1,3,3,3-hexafluoro-2-propylaminocarbonylamino and the like can be mentioned.

In the present invention, the "C ₁ to C ₆ alkylsulfonylamino group" means the above-mentioned meaning of the alkyl moiety unless otherwise specified (C ₁ to C ₆ alkyl) -S (= O) ₂ -NH- group. For example, a group such as methylsulfonylamino, ethylsulfonylamino, n-propylsulfonylamino, isopropylsulfonylamino or tert-butylsulfonylamino can be mentioned.

In the present invention, the "C ₁ to C ₆ haloalkylsulfonylamino group" means the above-mentioned meaning of the haloalkyl moiety unless otherwise specified (C ₁ to C ₆ haloalkyl) -S (= O) ₂ -NH- group. For example, fluoromethylsulfonylamino, difluoromethylsulfonylamino, trifluoromethylsulfonylamino, chloromethylsulfonylamino, trichloromethylsulfonylamino, 2,2,2-trifluoroethylsulfonylamino, 2,2-difluoroethylsulfonyl. Groups such as amino or 3,3,3-trifluoropropylsulfonylamino can be mentioned.

In the present invention, the "C ₃ to C ₆ cycloalkylsulfonylamino group" means the cycloalkyl moiety as described above (C ₃ to C ₆ cycloalkyl) -S (= O) _2- , unless otherwise specified. It indicates an NH-group, and examples thereof include groups such as cyclopropylsulfonylamino, cyclobutylsulfonylamino, cyclopentylsulfonylamino, and cyclohexylsulfonylamino.

In the present invention, the "tri (C ₁ to C ₆ alkyl) silyl group" means a (C ₁ to C ₆ alkyl) ₃ -Si- group in which the alkyl moiety has the above meaning unless otherwise specified, and 3 The alkyl groups may be the same or different from each other, and examples thereof include groups such as trimethylsilyl, triethylsilyl, triisopropylsilyl, dimethylisopropylsilyl and tert-butyldimethylsilyl.

In the present invention, the "1,3-benzodioxolyl group" is defined as, for example, 1,3-benzodioxole-4-yl or 1,3-benzodioxol-5-yl, unless otherwise specified. Etc. can be mentioned.

In the present invention, the term "heteroaryloxy group" means, unless otherwise specified, a (heteroaryl) -O-group in which the heteroaryl moiety has the above meaning, for example, (pyridin-2-yl) oxy, (pyridin-2-yl) oxy. Pyridine-3-yl) oxy, (pyridin-4-yl) oxy, (pyrimidine-2-yl) oxy, (pyrimidine-4-yl) oxy, (pyrimidine-5-yl) oxy, (pyridazine-3-yl) ) Oxy, (pyridazine-4-yl) oxy, (pyrazole-2-yl) oxy, (1,3,5-triazinin-2-yl) oxy, (thiazole-2-yl) oxy, (thiazole-4-yl) Il) oxy, (thiazole-5-yl) oxy, (pyrazole-1-yl) oxy, (pyrazole-3-yl) oxy, (pyrazole-4-yl) oxy or (pyrazole-5-yl) oxy, etc. The basis can be mentioned.

In the present invention, the "heterocycloalkyl group" indicates a 3- to 6-membered saturated heterocycle containing at least one atom selected from an oxygen atom, a nitrogen atom, and a sulfur atom in addition to a carbon atom, unless otherwise specified. For example, pyrrolidine-1-yl, piperidine-1-yl, oxetane-2-yl, oxetane-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-2-yl, tetrahydropyran-3. -Il or tetrahydropyran-4-yl and other groups can be mentioned.

In the present invention, "C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkyl groups" means the cycloalkyl moiety and the alkyl moiety as described above (C ₃ to C ₆ cycloalkyl) unless otherwise specified. (C ₁ to C ₆ alkyl) -groups, eg cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1- (cyclopropyl) ethyl, 2- (cyclopropyl) ethyl or 1- (cyclopropyl) ) A group such as propyl can be mentioned.

In the present invention, "C ₁ to C ₆ alkoxy C ₁ to C ₆ alkyl groups" means the above-mentioned meanings of the alkoxy moiety and the alkyl moiety unless otherwise specified (C ₁ to C ₆ alkoxy)-(C ₁ ). ~ C ₆ Alkyl) -indicates a group, eg, methoxymethyl, 1-methoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-methoxypropyl, 3-methoxypropyl, 2-ethoxypropyl, 3-ethoxypropyl, Groups such as 1-methyl-3-methoxybutyl or 3-butoxybutyl can be mentioned.

In the present invention, "C ₁ to C ₆ haloalkyl C ₁ to C ₆ alkyl groups" means the above-mentioned meanings of the haloalkoxy moiety and the alkyl moiety (C ₁ to C ₆ haloalkyl) unless otherwise specified. (C ₁ to C ₆ alkyl) -groups, eg 2- (difluoromethoxy) ethyl, 2- (trifluoromethoxy) ethyl, 2- (2,2-difluoroethoxy) ethyl, 2- (2,2) , 2-trifluoroethoxy) ethyl, 2- (3,3-difluoropropioxy) ethyl, 2- (3,3,3-trifluoropropioxy) ethyl, 3- (difluoromethoxy) propyl, 3- (tri) Fluoromethoxy) propyl, 3- (2,2-difluoroethoxy) propyl, 3- (2,2,2-trifluoroethoxy) propyl, 3- (3,3-difluoropropioxy) propyl, 3- (3) Groups such as 3,3-trifluoropropioxy) propyl, 4- (trifluoromethoxy) butyl or 5- (trifluoromethoxy) pentyl can be mentioned.

In the present invention, "C ₁ to C ₆ alkyl thio C ₁ to C ₆ alkyl groups" means the above-mentioned meanings of the alkyl thio moiety and the alkyl moiety unless otherwise specified (C ₁ to C ₆ alkyl thio)-(C ₁ ). ~ C ₆ Alkyl) -indicates a group, for example, methylthiomethyl, ethylthiomethyl, isopropylthiomethyl, 1-methylthioethyl, 2-methylthioethyl, 2-ethylthioethyl, 2-methylthiopropyl, 3-methylthiopropyl, 2 -Groups such as ethylthiopropyl or 3-ethylthiopropyl can be mentioned.

In the present invention, "C ₁ to C ₆ alkyl sulfinyl C ₁ to C ₆ alkyl groups" means the above-mentioned meanings of the alkyl sulfinyl moiety and the alkyl moiety unless otherwise specified (C ₁ to C ₆ alkyl sulfinyl)-. (C ₁ to C ₆ Alkyl) -Indicates a group, for example, methyl sulfinyl methyl, ethyl sulfinyl methyl, isopropylsulfinyl methyl, 1-methylsulfinyl ethyl, 2-methylsulfinyl ethyl, 2-ethylsulfinyl ethyl, 2-methylsulfinylpropyl. , 3-Methylsulfinylpropyl, 2-ethylsulfinylpropyl, 3-ethylsulfinylpropyl and the like.

In the present invention, "C ₁ to C ₆ alkyl sulfonyl C ₁ to C ₆ alkyl groups" means the above-mentioned meanings of the alkyl sulfonyl moiety and the alkyl moiety unless otherwise specified (C ₁ to C ₆ alkyl sulfonyl)-. (C ₁ to C ₆ Alkyl) -Indicates a group, for example, methyl sulfonyl methyl, ethyl sulfonyl methyl, isopropyl sulfonyl methyl, 1-methyl sulfonyl ethyl, 2-methyl sulfonyl ethyl, 2-ethyl sulfonyl ethyl, 2-methyl sulfonyl propyl. , 3-Methylsulfonylpropyl, 2-ethylsulfonylpropyl, 3-ethylsulfonylpropyl and the like.

In the present invention, "C ₁ to C ₆ haloalkylthio C ₁ to C ₆ alkyl groups" means the above-mentioned meanings of the haloalkylthio moiety and the alkyl moiety unless otherwise specified (C ₁ to C ₆ haloalkylthio)-. (C ₁ to C ₆ alkyl) -groups, eg, (difluoromethylthio) methyl, (trifluoromethylthio) methyl, (2,2-difluoroethylthio) methyl, (2,2,2-trifluoroethylthio) ) Methyl, 2- (difluoromethylthio) ethyl, 2- (trifluoromethylthio) ethyl, 2- (2,2-difluoroethylthio) ethyl, 2- (2,2,2-trifluoroethylthio) ethyl, 3 -Listing groups such as (difluoromethylthio) propyl, 3- (trifluoromethylthio) propyl, 3- (2,2-difluoroethylthio) propyl or 3- (2,2,2-trifluoroethylthio) propyl. Can be done.

In the present invention, "C ₁ to C ₆ haloalkyl sulfinyl C ₁ to C ₆ alkyl groups" means the above-mentioned meanings of the haloalkyl sulfinyl moiety and the alkyl moiety unless otherwise specified (C ₁ to C ₆ haloalkyl sulfinyl)-. (C ₁ to C ₆ alkyl) -groups such as (difluoromethylsulfinyl) methyl, (trifluoromethylsulfinyl) methyl, (2,2-difluoroethylsulfinyl) methyl, (2,2,2-trifluoro) Ethylsulfinyl) Methyl, 2- (difluoromethylsulfinyl) ethyl, 2- (trifluoromethylsulfinyl) ethyl, 2- (2,2-difluoroethylsulfinyl) ethyl, 2- (2,2,2-trifluoroethylsulfinyl) ) Ethyl, 3- (difluoromethylsulfinyl) propyl, 3- (trifluoromethylsulfinyl) propyl, 3- (2,2-difluoroethylsulfinyl) propyl or 3- (2,2,2-trifluoroethylsulfinyl) propyl Etc. can be mentioned.

In the present invention, "C ₁ to C ₆ haloalkyl sulfonyl C ₁ to C ₆ alkyl groups" means the haloalkyl sulfonyl moiety and the alkyl moiety as described above (C ₁ to C ₆ haloalkyl sulfonyl)-unless otherwise specified. (C ₁ to C ₆ alkyl) -groups, eg, (difluoromethylsulfonyl) methyl, (trifluoromethylsulfonyl) methyl, (2,2-difluoroethylsulfonyl) methyl, (2,2,2-trifluoro) Ethylsulfonyl) methyl, 2- (difluoromethylsulfonyl) ethyl, 2- (trifluoromethylsulfonyl) ethyl, 2- (2,2-difluoroethylsulfonyl) ethyl, 2- (2,2,2-trifluoroethylsulfonyl) ) Ethyl, 3- (difluoromethylsulfonyl) propyl, 3- (trifluoromethylsulfonyl) propyl, 3- (2,2-difluoroethylsulfonyl) propyl or 3- (2,2,2-trifluoroethylsulfonyl) propyl Etc. can be mentioned.

In the present invention, the "cyano C ₁ to C ₆ alkyl group" means a (cyano)-(C ₁ to C ₆ alkyl) group in which the alkyl moiety has the above meaning, unless otherwise specified, and for example, cyanomethyl. Groups such as 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropyl, 3-cyanopropyl, 2-cyanopropane-2-yl, 1-cyanobutyl, 4-cyanobutyl, 5-cyanopentyl or 6-cyanohexyl are mentioned. Can be done.

In the present invention, the "tri (C ₁ to C ₆ alkyl) silyloxy group" means a (C ₁ to C ₆ alkyl) ₃ -Si—O— group in which the alkyl moiety has the above meaning unless otherwise specified. The three alkyl groups may be the same or different from each other, and examples thereof include groups such as trimethylsilyloxy, triethylsilyloxy, triisopropylsilyloxy or tert-butyldimethylsilyloxy.

In the present invention, the "C ₁ to C ₆ alkoxyimino group" means, unless otherwise specified, the alkyl moiety has the above meaning (C ₁ to C ₆ alkyl) -ON = C- group, for example. , Methoxyimino, ethoxyimino, isopropoxyimino and the like.

In the present invention, "C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkyl groups" means the above-mentioned meanings of the halocycloalkyl moiety and the alkyl moiety (C ₃ to C ₆ halocyclo) unless otherwise specified. Alkyl)-(C ₁ to C ₆ alkyl) -groups, eg 2,2-difluorocyclopropylmethyl, 2,2-dichlorocyclopropylmethyl, 2- (2,2-difluorocyclopropyl) ethyl, 2 -(2,2-Dichlorocyclopropyl) ethyl, 2,2-difluorocyclobutylmethyl, 4,4-difluorocyclohexylmethyl and the like can be mentioned.

In the present invention, the "phenyl C ₁ to C ₆ alkyl group" refers to a phenyl- (C ₁ to C ₆ alkyl) -group in which the alkyl moiety has the above meaning, unless otherwise specified, for example, benzyl, 2 Groups such as -methylbenzyl, 2,3-dimethylbenzyl, 1-phenylethyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl, 5-phenylpentyl or 6-phenylhexyl can be mentioned.

In the present invention, the "carbon ring" means a non-aromatic 3- to 6-membered monocyclic atom in which all the atoms constituting the ring are 1 to 6 carbon atoms. Specific examples of the carbocycle include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cyclopropene, cyclobutene, cyclopentene, cyclohexene and the like.

In the present invention, the "heterocycle" means a carbon atom having 1 to 5 atoms constituting the ring, and a nitrogen atom, an oxygen atom and a sulfur atom (the sulfur atom is one or two oxo groups (= O)). It means a non-aromatic 3- to 6-membered heterocycle which is a heteroatom of 1 to 4 independently selected from (may be substituted with). Specific examples of the heterocycle include pyrrolidine, tetrahydrofuran, piperidine, tetrahydropyran, tetrahydrothiophene, tetrahydrothiopyran 1-oxide, tetrahydrothiopyran 1,1-dioxide, thiane, piperazine, morpholine, thiomorpholin, dioxane, dioxolan, Includes, but is not limited to, dithianes and the like.

In the present invention, "may be mono-substituted or poly-substituted by R ⁸ " means "may be substituted by one or more R ^8s ". When substituted with two or more ^R8s , the two or more ^R8s may be the _same or different, respectively, a halogen atom, a C1 to C6 alkyl group, _a C1 to _C6 haloalkyl group _, _a C3 to C. ₆ cycloalkyl group, C ₃ to C ₆ halocycloalkyl group, formyl group, C ₁ to C ₆ alkyl carbonyl group, C ₁ to C ₆ haloalkyl carbonyl group, C ₃ to C ₆ cycloalkyl carbonyl group, benzoyl group (the The group may be mono-substituted or poly-substituted with R ⁹ ), -C (R ¹⁰ ) = NOR ¹¹ , carboxy group, C _1-1 to C ₆ alkoxycarbonyl group, C ₁ to C ₆ haloalkoxycarbonyl group, aminocarbonyl. Groups, C ₁ to C ₆ alkylaminocarbonyl groups (the amino groups may be substituted with R ¹² ), C ₁ to C ₆ haloalkyl aminocarbonyl groups (the amino groups may be substituted with R ¹² ), Pyrrolidine-1-ylcarbonyl group (the group may be mono-substituted or poly-substituted with R ⁹ ), piperidin-1-ylcarbonyl group (the group may be mono-substituted or poly-substituted with R ⁹ ), Hydroxy group, C ₁ to C ₆ alkoxy group, C ₃ to C ₆ alkenyloxy group, C ₃ to C ₆ alkynyl oxy group, C ₁ to C ₆ haloalkoxy group, C ₃ to C ₆ cycloalkoxy group, C ₃ to C ₆ halocycloalkyl group, C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkoxy group, C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkoxy group, phenoxy group (the group is mono-substituted with R ⁹ or Poly-substituted), phenyl C ₁ to C ₆ alkoxy groups (the phenyl groups may be mono- or poly-substituted by R ⁹ ), thiol groups, C ₁ to C ₆ alkylthio groups, C ₁ to C. ₆ Alkyl sulphinyl groups, C ₁ to C ₆ alkyl sulfonyl groups, C ₁ to C ₆ haloalkyl thio groups, C ₁ to C ₆ haloalkyl sulphinyl groups, C ₁ to C ₆ haloalkyl sulfonyl groups, C ₃ to C ₆ cycloalkyl thio groups, C ₃ to C ₆ cycloalkylsulfinyl groups _, C3 to C6 cycloalkylsulfonyl groups _, C3 to _C6 _{halocycloalkylthio} groups, C3 to _C6 _{halocycloalkylsulfinyl} groups, C3 to _C6 _{halocycloalkylsulfonyl} groups Group, C ₃ to C ₆ Cloalkyl C ₁ to C ₆ alkylthio groups, C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkyl sulfinyl groups, C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkyl sulfonyl groups, C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkylthio groups, C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkyl sulfinyl groups, C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkyl sulfonyl groups, phenylthio groups (the groups are R ⁹ ). Mono-substituted or poly-substituted with R ^{9), phenylsulfinyl group (the group may be mono-substituted or poly-substituted with R 9} ⁾ , phenylsulfonyl group (the group may be mono-substituted or poly-substituted with R 9). May be), amino groups, C ₁ to C ₆ alkylamino groups (the amino groups may be substituted with R ¹² ), C ₁ to C ₆ haloalkyl amino groups (the amino groups may be substituted with R ¹² ). Good), _C ₁ to C ₆ alkylcarbonylamino groups (the amino groups may be substituted with ^R12 ), C1 to _C6 haloalkylcarbonylamino groups (the amino groups may be substituted with ^R12 ). , C ₃ to C ₆ cycloalkylcarbonylamino groups (the amino groups may be substituted with ^R12 ), phenylcarbonylamino groups (the phenyl groups may be mono- or poly-substituted with R9, the ^aminos ). The group may be substituted with R ¹² ), a C ₁ to C ₆ alkoxycarbonylamino group (the amino group may be substituted with R ¹² ), a C ₁ to C ₆ haloalkoxycarbonylamino group (the amino group). May be substituted with R ¹² ), C ₁ to C ₆ alkylaminocarbonylamino groups (the amino groups may be substituted with R ¹² ), C ₁ to C ₆ haloalkylaminocarbonylamino groups (the amino groups). May be substituted with R ¹² ), C ₁ to C ₆ alkylsulfonylamino groups (the amino groups may be substituted with R ¹² ), C ₁ to C ₆ haloalkylsulfonyl amino groups (the amino groups are R). ¹² may be substituted), C ₃ to C ₆ cycloalkylsulfonylamino groups (the amino groups may be substituted by ^R12 ), ^{phenylsulfonylamino} groups (the phenyl groups may be mono-substituted or poly by R9). It may be substituted, and the amino group may be substituted with ^R12 . ), Tri (C ₁ to C ₆ alkyl) silyl group, phenyl group (the group may be mono-substituted or poly-substituted with R ⁹ ), 1,3-benzodioxolyl group (the group may be R ⁹ ). Mono-substituted or poly-substituted), heteroaryl group (the group may be mono- or poly-substituted by R ⁹ ), heteroaryloxy group (the group may be mono- or poly-substituted by R ⁹ ). ( ^May be), a heterocycloalkyl group (the group may be mono-substituted or poly-substituted with R9), a cyano group, a nitro group or a thiocyanato group.

In the present invention, "may be mono-substituted or poly-substituted by R ⁹ " means "may be substituted by one or more R ^9s ". When substituted with two or more R ⁹ , the two or more R ^9s may be the same or different, respectively, a halogen atom, a C ₁ to C ₆ alkyl group, a C ₁ to C ₆ haloalkyl group, a C ₃ to C. ₆ cycloalkyl group, C ₃ to C ₆ halocycloalkyl group, hydroxy group, C ₁ to C ₆ alkoxy group, C ₁ to C ₆ haloalkoxy group, thiol group, C ₁ to C ₆ alkylthio group, C ₁ to C ₆ Alkyl sulphinyl group, C ₁ to C ₆ alkyl sulfonyl group, C ₁ to C ₆ haloalkylthio group, C ₁ to C ₆ haloalkyl sulphinyl group, C ₁ to C ₆ haloalkyl sulfonyl group, cyano group or nitro group.

In the present invention, the agriculturally acceptable salt is the compound of the present invention represented by the general formula [I] when a hydroxyl group, a carboxyl group, an amino group or the like is present in the structure or a nitrogen atom of the pyridine ring. , A salt of these with a metal or an organic base, or a salt of a mineral acid or an organic acid, and examples of the metal include an alkali metal such as sodium or potassium or an alkaline earth metal such as magnesium or calcium, and the organic base. Examples of the mineral acid include phosphoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, boric acid, sulfuric acid and the like, and examples of the organic acid include triethylamine and diisopropylamine. , Formic acid, acetic acid, lactic acid, ascorbic acid, succinic acid, fumaric acid, maleic acid, oxalic acid, citric acid, benzoic acid, salicylic acid, tartrate acid, methanesulfonic acid, 4-toluenesulfonic acid or trifluoromethanesulfonic acid. Can be done.

Next, Tables 1 to 37 show typical compound examples of the compounds included in the condensed heterocyclic derivative of the present invention represented by the general formula [I]. However, the compounds included in the derivatives of the present invention are not limited thereto. Further, the compound numbers in the table are referred to in the following description.

The compounds included in the fused heterocyclic derivative of the present invention may contain E-forms and Z-form geometric isomers depending on the type of substituent, but the present invention describes these E-forms. Includes Z-forms or mixtures containing E-forms and Z-forms in any proportion. Further, the compound included in the present invention may have optical isomers due to the presence of one or more asymmetric carbon atoms and asymmetric sulfur atoms, but the present invention has all optical activities. Includes body, racemic or diastereomers.

The following notations in the table herein represent, for example, the corresponding groups, respectively, as follows:
Me: Methyl;
Et: Ethyl;
n-Pr: n-propyl;
i-Pr: isopropyl;
n-Bu: n-butyl;
i-Bu: Isobutyl;
t-Bu: tert-butyl;
n-Pen: n-Pentil;
t-Pen: tert-pentyl;
n-Hex: n-hexyl;
c-Pr: Cyclopropyl;
c-Pen: Cyclopentyl;
c-Hex: Cyclohexyl;
CHF ₂ : Difluoromethyl;
CF ₃ : Trifluoromethyl;
Ph (4-CF ₃ ): 4-trifluoromethylphenyl;
Ph (2-F-4-CF ₃ ): 2-fluoro-4-trifluoromethylphenyl;
Ph (3,4,5-Cl ₃ ): 3,4,5-trichlorophenyl;
c-Pr (2,2 _- F2): 2,2-difluorocyclopropyl;

The compound of the present invention represented by the general formula [I] can be produced according to the production methods shown below, but is not limited to these methods. Hereinafter, for example, "compound represented by the general formula [I]", "compound represented by the formula [I]" and "compound [I]" have the same meaning.

<Manufacturing method 1>
Among the compounds of the present invention, the compound represented by the general formula [I-1] can be produced by using the compound represented by the general formula [II-1] according to the method represented by the reaction formula illustrated below. ..

(In the formula, K indicates K-1, K-2, K-3, K-4, K-5, K-6, K-7 or K-8.

L ¹ indicates a halogen atom or a methanesulfonyloxy group, and R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , m, Y, Z and A have the same meanings as described above. )

That is, the compound represented by the general formula [I-1] is a compound represented by the general formula [II-1] and the compound [IV-1] in the presence of a suitable catalyst in the presence of a suitable base. It can be produced by reacting under or in the absence of a suitable solvent.

The amount of the compound [IV-1] used in this reaction may be appropriately selected from the range of 1 to 100 mol per 1 mol of the compound [II-1], preferably 1.0 to 3.3 mol. Is.

Examples of the bases that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide. , Alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate; lithium hydride, sodium hydride, hydrogenation Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxydo, sodium ethoxydo, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N, N-dimethylaniline, pyridine, 2,6-lutidine , 4-N, N-dimethylaminopyridine, organic bases such as 1,8-diazabicyclo [5.4.0] -7-undecene and the like. The amount of the base used may be appropriately selected from the range of 1 to 5 mol with respect to 1 mol of the compound [II-1], and is preferably 1.0 to 2.0 mol.

Examples of the catalyst that can be used in this reaction include copper (I) chloride, copper (I) bromide, copper (I) iodide, and copper. The amount of the catalyst used may be appropriately selected from the range of 0.01 to 5 mol, preferably 0.01 to 1.2 mol, with respect to 1 mol of the compound [II-1].

Examples of the solvent that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methylhydrocarbon, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, and mesityrene. Aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide , Sulfolane, aprotonic polar solvents such as 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve; acetonitrile, propionitrile and the like. Nitriles; esters such as ethyl acetate, butyl acetate, ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; pyridines such as pyridine, picolin and lutidine; third such as triethylamine and tributylamine Secondary amines; water or a mixed solvent thereof and the like can be mentioned. The amount of the solvent used is 0.1 to 100 liters, preferably 0.3 to 25 liters, per 1 mol of the compound [II-1].

The reaction temperature of this reaction may be selected from an arbitrary temperature range from −30 ° C. to the reflux temperature in the reaction system, preferably in the range of 0 ° C. to 150 ° C.

The reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.

After completion of the reaction, the reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to isolate compound [I-1]. be able to. The isolated compound [I-1] can be further purified by column chromatography, recrystallization and the like, if necessary.

<Manufacturing method 2>
The compound represented by the general formula [II-3] can be produced by using the compound represented by the general formula [II-2] according to the method consisting of the reaction formulas exemplified below.

(In the formula, R ¹⁴ indicates a methyl group, an etanoyl group, a methoxymethyl group, a benzyl group or a 4-methoxybenzyl group, and R ¹ , R ⁴ , m and K have the same meanings as described above.)

That is, the compound represented by the general formula [II-3] is derived from the compound [II-2] from GREEN'S PROTECIVE GROUPS in Organic Synthesis; 5th Edition (John Wiley and Sons, 2014, Peter G. M. Wuts). It can be manufactured according to the method described in 1.

Compound [II-3] can be further purified by column chromatography, recrystallization, distillation or the like, if necessary.

<Manufacturing method 3>
Among the compounds of the present invention, the compound represented by the general formula [I-3] can be produced by using the compound represented by the general formula [I-2] according to the method represented by the reaction formula illustrated below. ..

(In the formula, R ^1a is a C ₁ to C ₆ alkyl group (the group may be mono-substituted or poly-substituted by R ⁸ ), a C ₂ -C ₆ alkenyl group (the group is mono-substituted or poly-substituted by R ⁸ ). Substituted) _, _C2 _- C6 alkynyl group (the group may be mono-substituted or poly ^- substituted with R8), C3 _- C6 cycloalkyl group ⁽ the group may be mono-substituted or poly-substituted with R8). Indicates a poly-substituted), phenyl group (the group may be mono- or poly-substituted by R ⁹ ) or a heteroaryl group (the group may be mono- or poly-substituted by R ⁹ ). , R ¹⁵ is a methyl group, an ethanoyl group, a methoxymethyl group, a benzyl group, a 4-methoxybenzyl group or

, L ² indicates a halogen atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, a nonafluorobutanesulfonyloxy group, a benzenesulfonyloxy group or a p ^- toluenesulfonyloxy group, ^R4 , ^R7 , R8, R ¹⁴ , m, Z, A and K have the same meanings as described above. )

That is, in the compound represented by the general formula [I-3], the compound [I-2] and the compound [IV-2] are mixed in a suitable solvent, in the presence of a suitable base, and in the presence of a suitable catalyst. Alternatively, it can be produced by reacting in the absence.

The amount of the compound [IV-2] used in this reaction may be appropriately selected from the range of 1.0 to 15.0 mol per 1 mol of the compound [I-2], and is preferably 1.0 to 1 mol. It is 6.0 mol.

Examples of the bases that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide. , Alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate; lithium hydride, sodium hydride, hydrogenation Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxydo, sodium ethoxydo, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N, N-dimethylaniline, pyridine, 2,6-lutidine , 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene and other organic bases and the like can be mentioned. The amount of the base used may be appropriately selected from the range of 1 to 5 mol with respect to 1 mol of the compound [I-2], and is preferably 1.0 to 1.5 mol.

Examples of the catalyst that can be used in this reaction include tetra-n-butylammonium bromide and tetra-n-butylammonium iodide. The amount of the catalyst used may be appropriately selected from the range of 0.01 to 1.0 mol with respect to 1 mol of the compound [I-2], and is preferably 0.05 to 0.5 mol.

Examples of the solvent that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methylhydrocarbon, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, and mesityrene. Aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide , Sulfolane, aprotonic polar solvents such as 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve; acetonitrile, propionitrile and the like. Nitriles; esters such as ethyl acetate, butyl acetate, ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; pyridines such as pyridine, picolin and lutidine; third such as triethylamine and tributylamine Secondary amines; water or a mixed solvent thereof and the like can be mentioned. The amount of the solvent used is 0.1 to 100 liters, preferably 0.1 to 50 liters, per 1 mol of the compound [I-2].

The reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 30 hours.

After completion of the reaction, the compound [I-3] can be isolated by pouring the reaction mixture into water or the like, extracting it with an organic solvent, and then concentrating it. The isolated compound [I-3] can be further purified by column chromatography, recrystallization and the like, if necessary.

<Manufacturing method 4>
Among the compounds of the present invention, the compounds represented by the general formulas [I-5] and [I-6] are the methods comprising the reaction formulas exemplified below using the compounds represented by the general formula [I-4]. Can be manufactured according to.

(In the formula, X is a halogen atom, A ² is CR ² or N, R ^3a is a C ₁ to C ₆ alkoxy group, C ₃ to C ₆ alkenyloxy group, C ₃ to C ₆ alkynyl oxy group, C ₁ to C ₆ haloalkoxy groups, C ₃ to C ₆ cycloalkoxy groups, C ₃ to C ₆ halocycloalkoxy groups, C ₃ to C ₆ cycloalkyls C ₁ to C ₆ alkoxy groups, C ₃ to C ₆ haloalkoxy groups Alkoxy C ₁ to C ₆ alkoxy groups, phenyl C ₁ to C ₆ alkoxy groups (the phenyl group may be mono-substituted or poly-substituted by R ⁹ ), heteroaryloxy groups (the groups may be mono-substituted or poly-substituted by R ⁹ ). May be poly-substituted), C ₁ to C ₆ alkylthio groups, C ₁ to C ₆ alkyl sulfonyl groups, C ₁ to C ₆ haloalkylthio groups or C ₁ to C ₆ haloalkyl sulfonyl groups, where R ^3b is C ₁ ~ C ₆ alkyl group, C ₂ ~ C _{6 alkoxy group, C 2 ~ C 6} _alkoxyyl _group , C ₁ ~ C ₆ haloalkyl group, C ₃ ~ C ₆ cycloalkyl group, C ₃ ~ C ₆ halocycloalkyl group, C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkyl groups, C ₃ to C ₆ ^{halocycloalkyl} C ₁ to C ₆ alkyl groups, phenyl C ₁ to C ₆ alkyl groups (the groups are mono-substituted or poly-substituted by R9). (May be) or a heteroaryl group (the group may be mono-substituted or poly-substituted by R ⁹ ), R ¹ , R ² , R ⁴ , R ⁷ , R ⁹ , R ¹⁵ , m and Z. Has the same meaning as above.)

(Step 4-1)
That is, the compound represented by the general formula [I-5] is produced by reacting compound [I-4] with a cyanide compound in a suitable solvent in the presence or absence of a suitable catalyst. be able to.

Examples of the cyanide compound used in this reaction include sodium cyanide, potassium cyanide, ammonium cyanide, zinc cyanide, copper cyanide, or a mixture thereof. The amount of the cyanide compound to be used may be appropriately selected from the range of 1 to 100 mol, preferably 1.0 to 5.0 mol, with respect to 1 mol of the compound [I-4].

Examples of the catalyst used in this reaction include tetrakis (triphenylphosphine) palladium, [1,1-bis (diphenylphosphino) ferrocene] palladium (II) dichloride dichloromethane adduct, and the like. The amount of the catalyst used may be appropriately selected from the range of 0.001 to 0.5 mol, preferably 0.01 to 0.2 mol, with respect to 1 mol of the compound [I-4]. be.

Examples of the solvent that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methylhydrocarbon, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, and mesityrene. Aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide , Sulfolane, aprotonic polar solvents such as 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve; acetonitrile, propionitrile and the like. Nitriles; esters such as ethyl acetate, butyl acetate, ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; pyridines such as pyridine, picolin and lutidine; third such as triethylamine and tributylamine Secondary amines; water or a mixed solvent thereof and the like can be mentioned. The amount of the solvent used is 0.1 to 500 liters, preferably 0.3 to 50 liters, per 1 mol of the compound [I-4].

The reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

After completion of the reaction, the compound is synthesized by filtering out the unnecessary substance from the reaction mixture and concentrating it as it is, or by pouring it into water and filtering out the precipitated solid or extracting it with an organic solvent and then concentrating it. [I-5] can be isolated. The isolated compound [I-5] can be further purified by column chromatography, recrystallization and the like, if necessary.

(Step 4-2)
That is, the compound represented by the general formula [I-6] is suitable for compound [I-4] and compound [IV-3] in a suitable solvent in the presence or absence of a suitable base. It can be produced by reacting in the presence of a catalyst.

The amount of the compound [IV-3] used in this reaction may be appropriately selected from the range of 1.0 to 15.0 mol with respect to 1 mol of the compound [I-4], preferably 1.0 to 1.0. It is 6.0 mol.

Examples of the bases that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide. , Alkaline metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate; lithium hydride, sodium hydride, hydrogenation Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxydo, sodium ethoxydo, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N, N-dimethylaniline, pyridine, 2,6-lutidine , 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene and other organic bases and the like can be mentioned. The amount of the base used may be appropriately selected from the range of 1 to 5 mol with respect to 1 mol of the compound [I-2], and is preferably 1.0 to 1.5 mol.

The catalyst that can be used in this reaction may be a transition metal complex or a combination of a transition metal and a ligand. For example, as the transition metal complex, tetrakis (triphenylphosphine) palladium (0), [1,1 -Bis (diphenylphosphino) ferrocene] palladium (II) dichloride dichloromethane adduct, bis (triphenylphosphine) palladium (II) dichloride, bis (dibenzylideneacetone) palladium (0), tris (dibenzylideneacetone) dipalladium ( Palladium catalyst such as 0), copper salt such as copper (I) iodide, trimethylphosphine, triethylphosphine, tributylphosphine, triphenylphosphine, 1,3-bisdimethylphosphinopropane, 1,2- Bisdiphenylphosphinoetan, 1,3-bisdiphenylphosphinopropane, 4,5-bis (diphenylphosphino) -9.9-dimethylxanthene, 1,10-phenanthroline, 3,4,7,8-tetramethyl -1,10-Phenantrolin and the like can be mentioned. The amount of the catalyst used is 0.001 to 0.1 mol, preferably 0.01 to 0.05 mol, based on 1 mol of the compound [I-4].

After completion of the reaction, unnecessary substances are filtered out from the reaction mixture and concentrated, or the reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated. , Compound [I-6] can be isolated. The isolated compound [I-6] can be further purified by column chromatography, recrystallization and the like, if necessary.

<Manufacturing method 5>
Among the compounds of the present invention, the compound represented by the general formula [I-4] can be produced by using the compound represented by the general formula [I-7] according to the method consisting of the reaction formulas exemplified below. ..

(In the formula, R ¹ , R ⁴ , R ¹⁵ , m, A ² , X and Z have the same meanings as described above.)

That is, the compound represented by the general formula [I-4] is produced by reacting the compound [I-7] with a halogenating agent in a suitable solvent in the presence or absence of a suitable base. can do.

The halogenating agents that can be used in this reaction include chlorine, sulfryl chloride, N-chlorosuccinate imide, sodium hypochlorite, bromine, N-bromosuccinimide, 1,3-dibromo-5,5-dimethylhydantoin, and iodine. , N-iodosuccinic acidimide, 1,3-diiodo-5,5-dimethylhydantin, potassium iodate, or a mixture thereof. The amount of the halogenating agent used may be appropriately selected from the range of 0.01 to 10 mol, preferably 0.02 to 2.0 mol, with respect to 1 mol of the compound [I-7].

Examples of the bases that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide. , Alkaline metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate; lithium hydride, sodium hydride, hydrogenation Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxydo, sodium ethoxydo, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N, N-dimethylaniline, pyridine, 2,6-lutidine , 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene and other organic bases and the like can be mentioned. The amount of the base used may be appropriately selected from the range of 1 to 5 mol with respect to 1 mol of the compound [I-7], and is preferably 1.0 to 3.0 mol.

Examples of the solvent that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methylhydrocarbon, 1,4-dioxane, and monoglime; dichloromethane, chloroform, 1,2-. Hydrocarbons such as dichloroethane; non-N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and the like Protonic polar solvents; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; carboxylic acids such as acetic acid, propionic acid and trifluoroacetic acid; hydrochloric acid and hydrobromic acid , Inorganic acids such as sulfuric acid, nitric acid, and phosphoric acid; water or a mixed solvent thereof and the like can be mentioned. The amount of the solvent used is 0.1 to 300 liters, preferably 0.3 to 20 liters, per 1 mol of the compound [I-7].

The reaction temperature of this reaction may be selected from an arbitrary temperature range from −70 ° C. to the reflux temperature in the reaction system, preferably in the range of −20 ° C. to 100 ° C.

After completion of the reaction, the reaction mixture is poured into water or the reaction mixture is concentrated as it is, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated. -4] can be isolated. The isolated compound [I-4] can be further purified by column chromatography, recrystallization and the like, if necessary.

<Manufacturing method 6>
The compound represented by the general formula [II-4] can be produced by using the compound represented by the general formula [III-1] according to the method consisting of the reaction formulas exemplified below.

(In the formula, R ^3c is a hydrogen atom, C ₁ to C ₆ alkyl group, C ₂ to C ₆ alkenyl group, C ₂ to C ₆ alkynyl group, C ₁ to C ₆ haloalkyl group, C ₃ to C ₆ cycloalkyl group. , C ₃ to C ₆ halocycloalkyl groups, C ₁ to C ₆ alkoxy C ₁ to C ₆ alkyl groups, C ₁ to C ₆ haloalkyl C ₁ to C ₆ alkyl groups, R ⁴ , R ¹⁴ , m, X and Z have the same meanings as described above.)

That is, the compound represented by the general formula [II-2] is produced by reacting compound [III-1] with hydrazine in a suitable solvent in the presence or absence of a suitable base. Can be done.

Examples of the hydrazine that can be used in this reaction include anhydrous hydrazine, hydrazine hydrate, and hydrazine hydrochloride. The amount of hydrazine used may be appropriately selected from the range of 1 to 30 mol with respect to 1 mol of the compound [III-1], and is preferably 1 to 20 mol.

Examples of the bases that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide. , Alkaline metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate; lithium hydride, sodium hydride, hydrogenation Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxydo, sodium ethoxydo, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N, N-dimethylaniline, pyridine, 2,6-lutidine , 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene and other organic bases and the like can be mentioned. The amount of the base used may be appropriately selected from the range of 1 to 5 mol with respect to 1 mol of the compound [III-1], and is preferably 1.0 to 1.5 mol.

Solvents that can be used in this reaction include, for example, ethers such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methyltetrachloride, 1,4-dioxane, monoglime; N, N-dimethylformamide, N. , N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and other aprotic polar solvents; methanol, ethanol, 2-propanol, tert-butyl Alcohols such as alcohol and methylformamide; nitriles such as acetonitrile and propionitrile; pyridines such as pyridine, picolin and lutidine; tertiary amines such as triethylamine and tributylamine; water or a mixed solvent thereof and the like. be able to. The amount of the solvent used is 0.1 to 300 liters, preferably 0.3 to 20 liters, per 1 mol of the compound [III-1].

After completion of the reaction, the reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to isolate compound [II-4]. be able to. The isolated compound [II-4] can be further purified by column chromatography, recrystallization and the like, if necessary.

<Manufacturing method 7>
The compound represented by the general formula [III-1] can be produced by using the compound represented by the general formula [III-2] according to the method consisting of the reaction formulas exemplified below.

(In the formula, L ³ indicates a halogen atom, C ₁ to C ₆ alkoxy groups, -OC (= O) R ^3c , -N (Me) OME, and R ^3c , R ⁴ , R ¹⁴ , m, X and Z has the same meaning as described above.)

That is, the compound represented by the general formula [III-1] is produced by reacting compound [III-2] and compound [IV-4] in a suitable solvent in the presence of a suitable base. be able to.

The amount of the compound [IV-4] used in this reaction may be appropriately selected from the range of 1 to 15 mol with respect to 1 mol of the compound [III-2], preferably 1.0 to 3.0 mol. Is.

Examples of the base that can be used in this reaction include lithium diisopropylamide, lithium bis (trimethylsilyl) amide, sodium bis (trimethylsilyl) amide, and potassium bis (trimethylsilyl) amide. The amount of the base used may be appropriately selected from the range of 1 to 5 mol with respect to 1 mol of the compound [III-2], and is preferably 1.0 to 1.5 mol.

Examples of the solvent that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methylhydrocarbon, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, and mesityrene. Aromatic hydrocarbons such as chlorobenzene; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; or a mixed solvent thereof and the like can be mentioned. The amount of the solvent used is 0.1 to 300 liters, preferably 0.3 to 20 liters, per 1 mol of the compound [III-2].

The reaction temperature of this reaction may be selected from an arbitrary temperature range from −100 ° C. to the reflux temperature in the reaction system, preferably in the range of −100 ° C. to 40 ° C.

After completion of the reaction, the reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to isolate compound [III-1]. be able to. The isolated compound [III-1] can be further purified by column chromatography, recrystallization and the like, if necessary.

<Manufacturing method 8>
The compound represented by the general formula [II-5] can be produced by using the compound represented by the general formula [III-3] according to the method consisting of the reaction formulas exemplified below.

(In the formula, R ^1a , R ⁴ , R ¹⁴ , m and Z have the same meanings as described above.)

That is, the compound represented by the general formula [II-5] can be produced by reacting the compound [III-3] with a nitrite or a nitrite in an appropriate solvent.

Examples of the nitrite or nitrite ester that can be used in this reaction include sodium nitrite, t-butyl nitrite, and isoamyl nitrite. The amount of nitrite or nitrite used may be appropriately selected from the range of 1 to 5 mol with respect to 1 mol of the compound [III-3], and is preferably 1.0 to 2.5 mol.

Solvents that can be used in this reaction include, for example, ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyl tetrahydrofuran, 1,4-dioxane, monoglime; dichloromethane, chloroform, 1,2-. Halogenized hydrocarbons such as dichloroethane; nitriles such as acetonitrile and propionitrile; carboxylic acids such as acetic acid, propionic acid and trifluoroacetic acid; inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitrate and phosphoric acid; Water or a mixed solvent thereof and the like can be mentioned. The amount of the solvent used is 0.1 to 300 liters, preferably 0.3 to 20 liters, per 1 mol of the compound [III-3].

The reaction temperature of this reaction may be selected from an arbitrary temperature range from −20 ° C. to the reflux temperature in the reaction system, preferably in the range of −10 ° C. to 40 ° C.

After completion of the reaction, the reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to isolate compound [II-5]. be able to. The isolated compound [II-5] can be further purified by column chromatography, recrystallization and the like, if necessary.

<Manufacturing method 9>
The compound represented by the general formula [III-3] can be produced, for example, by using the compound represented by the general formula [III-4] according to the method consisting of the reaction formulas exemplified below.

That is, the compound represented by the general formula [III-3] is represented by the general formula [III-4] according to the "general reduction section" of the 4th edition (Maruzen) of the Experimental Chemistry Course, Volume 26. It can be produced by reducing the nitro compound.

Compound [III-3] can be further purified by column chromatography, recrystallization, distillation, etc., if necessary.

<Manufacturing method 10>
The compound represented by the general formula [III-4] can be produced, for example, by using the compound represented by the general formula [III-5] according to the method consisting of the reaction formulas exemplified below.

(In the formula, R ^1a , R ⁴ , R ¹⁴ , m, L ² and Z have the same meanings as described above.)

That is, in the compound represented by the general formula [III-4], the compound [III-5] and the compound [IV-2] are mixed in a suitable solvent, in the presence of a suitable base, and in the presence of a suitable catalyst. Alternatively, it can be produced by reacting in the absence.

The compound [IV-2], base, catalyst, solvent, reaction temperature and reaction time that can be used in this reaction are the same as in Production Method 3.

After completion of the reaction, the reaction mixture is poured into water, and the precipitated solid is collected by filtration, or extracted with an organic solvent and then concentrated to isolate compound [III-4]. can do. The isolated compound [III-4] can be further purified by column chromatography, recrystallization and the like, if necessary.

<Manufacturing method 11>
The compound represented by the general formula [II-6] can be produced, for example, by using the compound represented by the general formula [III-3] according to the method consisting of the reaction formulas exemplified below.

(In the formula, L ⁴ represents a halogen atom, —OC (= O) R ² , R ¹⁶ represents a C ₁ to C ₆ alkyl group, and R ^1a , R ² , R ⁴ , R ¹⁴ , m and Z represent. It has the same meaning as above.)

That is, in the compound represented by the general formula [II-6], the compound [III-3] and the compound [IV-5] or the compound [IV-6] are mixed in a suitable solvent in the presence of a suitable acid. Alternatively, it can be produced by reacting in the absence or in the presence or absence of a suitable base.

The amount of the compound [IV-5] or the compound [IV-6] used in this reaction may be appropriately selected from the range of 1 mol to the equivalent amount of the solvent amount per 1 mol of the compound [III-3]. It is preferably 1.0 to 10.0 mol. However, the compound [IV-6] can also be used as the above-mentioned solvent.

Examples of the acid that can be used in this reaction include inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, and phosphoric acid; carboxylic acids such as acetic acid, propionic acid, and trifluoroacetic acid; methanesulfonic acid and trifluoromethanesulfonic acid. Sulfonic acids and the like can be mentioned. The amount of the acid to be used may be appropriately selected from the range of 0.1 to 1 mol corresponding to the amount of the solvent with respect to 1 mol of the compound [III-3], and is preferably 0.1 to 100.0 mol.

Examples of the bases that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide. , Alkaline metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate; lithium hydride, sodium hydride, hydrogenation Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxydo, sodium ethoxydo, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N, N-dimethylaniline, pyridine, 2,6-lutidine , 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene and other organic bases and the like can be mentioned. The amount of the base used may be appropriately selected from the range of 1 to 5 mol with respect to 1 mol of the compound [III-3], and is preferably 1.0 to 1.5 mol.

Solvents that can be used in this reaction include, for example, ethers such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methyltetracarbonate, 1,4-dioxane, monoglime; benzene, toluene, xylene, mesityrene, etc. Aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide , Sulfolane, aprotonic polar solvents such as 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve; acetonitrile, propionitrile and the like. Nitriles; esters such as ethyl acetate, butyl acetate, ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; pyridines such as pyridine, picolin and rutidin; third such as triethylamine and tributylamine. Secondary amines; orthoesters such as trimethyl orthoacetate, triethyl orthoacetate, trimethyl orthoacetate, triethyl orthoacetate and the like, or a mixed solvent thereof and the like can be mentioned. The amount of the solvent used is 0.1 to 100 liters, preferably 0.1 to 15 liters, per 1 mol of the compound [III-3].

The reaction temperature of this reaction may be usually selected from an arbitrary temperature range from −30 ° C. to the reflux temperature in the reaction system, preferably in the range of −10 ° C. to 150 ° C.

After completion of the reaction, the compound [II-6] is isolated by concentrating the reaction mixture as it is, or by pouring the reaction mixture into water or the like, extracting with an organic solvent, and then concentrating the reaction mixture. can do. The isolated compound [II-6] can be further purified by column chromatography, recrystallization and the like, if necessary.

<Manufacturing method 12>
The compound represented by the general formula [II-7] can be produced, for example, by using the compound represented by the general formula [III-6] according to the method consisting of the reaction formulas exemplified below.

(In the formula, R ^1a , R ⁴ , m and Z have the same meanings as described above.)

That is, the compound represented by the general formula [II-7] can be produced by reacting the compound [III-6] with carbon disulfide in a suitable solvent in the presence of a suitable base. ..

The amount of carbon disulfide used in this reaction may be appropriately selected from the range of 1 to 35 mol per 1 mol of the compound [III-6], and is preferably 1 to 25 mol.

Examples of the bases that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide. , Alkaline metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate; lithium hydride, sodium hydride, hydrogenation Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxydo, sodium ethoxydo, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N, N-dimethylaniline, pyridine, 2,6-lutidine , 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene and other organic bases and the like can be mentioned. The amount of the base used may be appropriately selected from the range of 1 to 5 mol with respect to 1 mol of the compound [III-6], and is preferably 1.0 to 2.0 mol.

Examples of the solvent that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methylhydrocarbon, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, and mesityrene. Aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide , Sulfolane, aprotonic polar solvents such as 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve; acetonitrile, propionitrile and the like. Nitriles; esters such as ethyl acetate, butyl acetate, ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; pyridines such as pyridine, picolin and lutidine; third such as triethylamine and tributylamine Secondary amines; water or a mixed solvent thereof and the like can be mentioned. The amount of the solvent used is 0.1 to 100 liters, preferably 0.1 to 15 liters, per 1 mol of the compound [III-6].

After completion of the reaction, the compound [II-7] can be isolated by pouring the reaction mixture into water or the like, extracting it with an organic solvent, and then concentrating it. The isolated compound [II-7] can be further purified by column chromatography, recrystallization and the like, if necessary.

<Manufacturing method 13>
The compound represented by the general formula [III-6] can be produced, for example, by using the compound represented by the general formula [III-7] according to the method consisting of the reaction formulas exemplified below.

(In the formula, R ¹⁷ represents -C (= O) Me, -C (= O) Ph, -CH ₂ OME, -CH ₂ SMe, a tri (C ₁ to C ₆ alkyl) silyl group, and R ¹⁸ is H, Me, O (t-Bu) are shown, and R ^1a , R ⁴ , m and Z have the same meanings as described above.)

That is, the compound represented by the general formula [III-6] can be produced by reacting the compound [III-7] in a suitable solvent in the presence of a suitable acid.

Examples of the acid that can be used in this reaction include inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, and phosphoric acid; carboxylic acids such as acetic acid, propionic acid, and trifluoroacetic acid; methanesulfonic acid and trifluoromethanesulfonic acid. Sulfonic acids and the like can be mentioned. The amount of the acid used may be appropriately selected from the range of 0.1 to 1 mol corresponding to the amount of the solvent with respect to 1 mol of the compound [III-7], and is preferably 0.1 to 100 mol.

Solvents that can be used in this reaction include, for example, ethers such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methyltetrachloride, 1,4-dioxane, monoglyme; benzene, toluene, xylene, mesityrene, etc. Aromatic hydrocarbons such as chlorobenzene; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol and methyl cellosolve; water or a mixed solvent thereof and the like can be mentioned. The amount of the solvent used is 0.1 to 100 liters, preferably 0.1 to 25 liters, per 1 mol of the compound [III-6].

After completion of the reaction, the compound [III-6] can be isolated by pouring the reaction mixture into water or the like, extracting it with an organic solvent, and then concentrating it. The isolated compound [III-6] can be further purified by column chromatography, recrystallization and the like, if necessary.

<Manufacturing method 14>
The compound represented by the general formula [III-7] can be produced, for example, by using the compound represented by the general formula [III-8] according to the method consisting of the reaction formulas exemplified below.

(In the formula, R ^1a , R ⁴ , R ¹⁷ , R ¹⁸ , m, L ² and Z have the same meanings as described above.)

That is, in the compound represented by the general formula [III-7], the compound [III-8] and the compound [IV-2] are mixed in a suitable solvent, in the presence of a suitable base, and in the presence of a suitable catalyst. Alternatively, it can be produced by reacting in the absence.

After completion of the reaction, the reaction mixture is poured into water, and the precipitated solid is collected by filtration, or extracted with an organic solvent and then concentrated to isolate compound [III-7]. can do. The isolated compound [III-7] can be further purified by column chromatography, recrystallization and the like, if necessary.

<Manufacturing method 15>
The compound represented by the general formula [III-8] can be produced, for example, by using the compound represented by the general formula [III-9] according to the method consisting of the reaction formulas exemplified below.

(In the formula, L ⁵ represents a halogen atom, —OC (= O) R ¹⁸ , C ₁ to C ₆ alkyl groups, 1,1-dioxide-3-oxobenzothiazole-2-yl, R ⁴ , R ¹⁷ , R ¹⁸ , m and Z have the same meanings as described above.)

That is, the compound represented by the general formula [III-8] is derived from the compound [III-9] from GREEN'S PROTECIVE GROUPS in Organic Synthesis; 5th Edition (John Wiley and Sons, 2014, Peter G. M. Wuts). It can be manufactured according to the method described in 1.

Compound [III-8] can be further purified by column chromatography, recrystallization, distillation, etc., if necessary.

<Manufacturing method 16>
Among the compounds of the present invention, the compound represented by the general formula [I-8] is produced, for example, by using the compound represented by the general formula [III-10] according to the method consisting of the reaction formulas exemplified below. be able to.

(In the formula, L ⁶ indicates a leaving group such as 1H-imidazole-1-yl, -OCCl ₃ , -NH ₂ , -O (imidyl N-succinate), R ⁴ , R ⁷ , m, Z and A has the same meaning as described above.)

That is, the compound represented by the general formula [I-8] is produced by reacting compound [III-10] and compound [IV-8] in a suitable solvent in the presence of a suitable base. be able to.

The amount of the compound [IV-8] used in this reaction may be appropriately selected from the range of 1 to 15 mol, preferably 1.0 to 5.0 mol, with respect to 1 mol of the compound [III-10]. Is.

Examples of the bases that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide. , Alkaline metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate; lithium hydride, sodium hydride, hydrogenation Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxydo, sodium ethoxydo, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N, N-dimethylaniline, pyridine, 2,6-lutidine , 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene and other organic bases and the like can be mentioned. The amount of the base used may be appropriately selected from the range of 1 to 5 mol with respect to 1 mol of the compound [III-10], and is preferably 1.0 to 1.5 mol.

Examples of the solvent that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methylhydrocarbon, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, and mesityrene. Aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide , Sulfolane, aprotonic polar solvents such as 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve; acetonitrile, propionitrile and the like. Nitriles; esters such as ethyl acetate, butyl acetate, ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; pyridines such as pyridine, picolin and lutidine; third such as triethylamine and tributylamine Secondary amines; water or a mixed solvent thereof and the like can be mentioned. The amount of the solvent used is 0.1 to 100 liters, preferably 0.1 to 80 liters, per 1 mol of the compound [III-10].

After completion of the reaction, the compound [I-8] can be isolated by pouring the reaction mixture into water or the like, extracting it with an organic solvent, and then concentrating it. The isolated compound [I-8] can be further purified by column chromatography, recrystallization and the like, if necessary.

<Manufacturing method 17>
The compound represented by the general formula [III-11] can be produced, for example, by using the compound represented by the general formula [III-12] according to the method consisting of the reaction formulas exemplified below.

(In the formula, R ⁴ , R ⁷ , R ¹⁴ , m and A have the same meanings as described above.)

That is, the compound represented by the general formula [III-11] is derived from the compound [III-12] from GREEN'S PROTECIVE GROUPS in Organic Synthesis; 5th Edition (John Wiley and Sons, 2014, Peter G. M. Wuts). It can be manufactured according to the method described in 1.

The compound [III-11] can be further purified by column chromatography, recrystallization, distillation or the like, if necessary.

<Manufacturing method 18>
The compound represented by the general formula [III-12] can be produced, for example, by using the compound represented by the general formula [III-13] according to the method consisting of the reaction formulas exemplified below.

That is, the compound represented by the general formula [III-12] is represented by the general formula [III-13] according to the "general reduction section" of the 4th edition (Maruzen) of the Experimental Chemistry Course, Volume 26. It can be produced by reducing the nitro compound.

Compound [III-12] can be further purified by column chromatography, recrystallization, distillation, etc., if necessary.

<Manufacturing method 19>
The compound represented by the general formula [III-13] can be produced, for example, by using the compound represented by the general formula [III-14] according to the method consisting of the reaction formulas exemplified below.

(In the formula, R ⁴ , R ⁷ , R ¹⁴ , m, L ¹ and A have the same meanings as described above.)

That is, the compound represented by the general formula [III-13] is a compound represented by the general formula [III-14] and the compound [IV-1] in the presence of a suitable catalyst in the presence of a suitable base. It can be produced by reacting under or in the absence of a suitable solvent.

The compound [IV-1], base, catalyst, solvent, reaction temperature and reaction time that can be used in this reaction are the same as in Production Method 1.

After completion of the reaction, the reaction mixture is poured into water, and the precipitated solid is collected by filtration, or extracted with an organic solvent and then concentrated to isolate compound [III-13]. can do. The isolated compound [III-13] can be further purified by column chromatography, recrystallization and the like, if necessary.

<Manufacturing method 20>
The compound represented by the general formula [III-14] can be produced, for example, by using the compound represented by the general formula [III-15] according to the method consisting of the reaction formulas exemplified below.

(In the formula, R ⁴ , R ¹⁴ , m and X have the same meanings as described above.)

That is, the compound represented by the general formula [III-14] can be produced by reacting the compound [III-15] with sodium sulfide or sodium hydrogen sulfide in an appropriate solvent.

The amount of sodium sulfide or sodium hydrogen sulfide used in this reaction may be appropriately selected from the range of 1 to 15 mol with respect to 1 mol of the compound [III-15], preferably 1.0 to 3.0 mol. Is.

Examples of the solvent that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methyltetrachloride, 1,4-dioxane, and monoglyme; N, N-dimethylformamide, N. , N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and other aprotonic polar solvents; methanol, ethanol, 2-propanol, tert-butyl Alcohols, alcohols such as methyl cellosolve; water or a mixed solvent thereof and the like can be mentioned. The amount of the solvent used is 0.1 to 100 liters, preferably 0.1 to 15 liters, per 1 mol of the compound [III-15].

The reaction temperature of this reaction may be selected from an arbitrary temperature range from −30 ° C. to the reflux temperature in the reaction system, preferably in the range of 0 ° C. to 100 ° C.

After completion of the reaction, the compound [III-14] can be isolated by pouring the reaction mixture into water or the like, extracting it with an organic solvent, and then concentrating it. The isolated compound [III-14] can be further purified by column chromatography, recrystallization and the like, if necessary.

<Manufacturing method 21>
Among the compounds of the present invention, the compound represented by the general formula [I-10] is produced, for example, by using the compound represented by the general formula [I-9] according to the method consisting of the reaction formulas exemplified below. be able to.

(In the formula, R ¹ , R ⁴ , R ¹⁵ , m and Z have the same meanings as described above.)

That is, the compound represented by the general formula [I-10] can be produced by reacting the compound [I-9] with a nucleophilic fluorinating agent in an appropriate solvent.

Examples of the nucleophilic fluorinating agent that can be used in this reaction include (diethylamino) sulfatrifluoride and bis (2-methoxyethyl) aminosulfatrifluoride. The amount of the nucleophilic fluorinating agent to be used may be appropriately selected from the range of 2 to 10 mol with respect to 1 mol of the compound [I-9], and is preferably 2.0 to 5.0 mol.

Examples of the solvent that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methylhydrocarbon, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, and mesityrene. Aromatic hydrocarbons such as chlorobenzene; Halogenized hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; Alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve; acetonitrile, propio Nitriles such as nitriles; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane, or mixed solvents thereof and the like can be mentioned. The amount of the solvent used is 0.1 to 100 liters, preferably 0.1 to 15 liters, per 1 mol of the compound [I-9].

The reaction temperature of this reaction may be usually selected from an arbitrary temperature range from −30 ° C. to the reflux temperature in the reaction system, preferably in the range of −10 ° C. to 60 ° C.

After completion of the reaction, the compound [I-10] can be isolated by pouring the reaction mixture into water or the like, extracting it with an organic solvent, and then concentrating it. The isolated compound [I-10] can be further purified by column chromatography, recrystallization and the like, if necessary.

The herbicide of the present invention contains a fused heterocyclic derivative represented by the general formula [I] of the present invention or an agriculturally acceptable salt thereof as an active ingredient. The herbicides of the present invention have excellent herbicidal efficacy, and some show excellent selectivity between useful plants and weeds, and are useful as pesticide compositions in agricultural land, especially as herbicides. That is, the compound of the present invention can be used for foliage treatment, soil treatment, seed powder coating treatment, soil mixing treatment, pre-sowing soil treatment, simultaneous sowing treatment, post-sowing soil treatment, and sowing in fields where useful plants are cultivated or non-agricultural land. It has a herbicidal effect on various weeds in the simultaneous soil covering and mixing treatment.

The herbicide of the present invention can contain an additive component (carrier) usually used in a pesticide preparation, if necessary.

Examples of the additive component include carriers such as solid carriers or liquid carriers, surfactants, binders and tackifiers, thickeners, colorants, spreading agents, spreading agents, antifreeze agents, anti-caking agents, and the like. Examples thereof include a disintegrant, a decomposition inhibitor, and the like, and if necessary, a preservative, a plant piece, or the like may be used as an additive component. Further, these additive components may be used alone or in combination of two or more.

The above additive components will be described below.

Examples of the solid carrier include pyrophyllite clay, kaolin clay, silica stone clay, talc, diatomaceous earth, zeolite, bentonite, acidic white clay, active white clay, attapargas clay, vermiculite, pearlite, peasite, and white carbon (synthetic silicic acid,). Mineral carriers such as synthetic silicate), titanium dioxide; vegetable carriers such as wood flour, corn stalks, walnut shells, fruit nuclei, fir, fir, oak, bran, soybean flour, powdered cellulose, starch, dextrin, sugars, etc.; Inorganic salt carriers such as calcium carbonate, ammonium sulfate, sodium sulfate, potassium chloride; and polymer carriers such as polyethylene, polypropylene, polyvinyl chloride, polyvinyl acetate, ethylene-vinyl acetate copolymer, and urea-aldehyde resin can be mentioned. can.

Examples of the liquid carrier include monohydric alcohols such as methanol, ethanol, propanol, 2-propanol, butanol, and cyclohexanol; and many such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin. Hyvalent alcohols; Polyhydric alcohol derivatives such as propylene glycol ethers; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, isophorone; ethyl ether, 1,4-dioxane, cellosolve, dipropyl ether, Ethers such as tetrahydrofuran; aliphatic hydrocarbons such as normal paraffin, naphthene, isoparaffin, kerosine, mineral oil; fragrances such as toluene, C ₉ -C ₁₀ alkylbenzene, xylene, solvent naphtha, alkylnaphthalene, high boiling aromatic hydrocarbons, etc. Group hydrocarbons; Halogenized hydrocarbons such as 1,2-dichloroethane, chloroform, carbon tetrachloride; Esters such as ethyl acetate, diisopropylphthalate, dibutylphthalate, dioctylphthalate, dimethyl adipate; lactones such as γ-butyrolactone Classes; amides such as N, N-dimethylformamide, N, N-diethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone; nitriles such as acetonitrile; sulfur compounds such as dimethylsulfoxide; large Vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, coconut oil, and castor oil, lower alkyl esters of fatty acids derived from the vegetable oils; water and the like can be mentioned.

Examples of the surfactant include sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, polyoxyethylene alkyl ether, and poly. Oxyethylene alkylphenyl ether, polyoxyethylene dialkylphenyl ether, polyoxyethylene alkylphenyl ether formalin condensate, polyoxyethylene polyoxypropylene block polymer, alkylpolyoxyethylene polypropylene block polymer ether, polyoxyethylene alkylamine, polyoxyethylene Fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styrylphenyl ether, acetylene diol, polyoxyalkylene-added acetylene diol, polyoxyethylene ether type silicone, ester type silicone, fluorine-based surfactant , Polyoxyethylene castor oil, nonionic surfactants such as polyoxyethylene hydrogenated castor oil; alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkylphenyl ether sulfates, polyoxyethylene styrylphenyl ether sulfates, Alkylbenzene sulfonate, lignin sulfonate, alkylsulfosuccinate, naphthalene sulfonate, alkylnaphthalene sulfonate, formalin condensate salt of naphthalene sulfonic acid, formalin condensate salt of alkylnaphthalene sulfonic acid, fatty acid salt, Anionic surfactants such as polycarboxylate, N-methyl-fatty acid sarcosinate, resinate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl phenyl ether phosphate; laurylamine hydrochloride, stearylamine hydrochloride Cationic surfactants such as salts, alkylamine salts such as oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride, alkyldimethylbenzalconium chloride; dialkyldiaminoethylbetaine, alkyldimethylbenzylbetaine Such as betaine type, dialkylaminoethyl glycine, alkyldimethylbenzyl glycine and other amino acid type and the like can be mentioned.

Examples of the binder and tackifier include carboxymethyl cellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sugar, polyvinylpyrrolidone, arabic rubber, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol and polyethylene. Oxides, natural phospholipids (eg, cepharic acid, lecithin, etc.) and the like can be mentioned.

Thickeners include, for example, xanthan gum, guar gum, carboxymethyl cellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch derivatives, water-soluble polymers such as polysaccharides; high-purity bentonite, inorganic fine powder such as white carbon. , Organic fine powder such as organic bentnite can be mentioned.

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 metallic phthalocyanine dyes.

Examples of the spreading agent include silicone-based surfactants, cellulose powders, dextrins, processed starches, polyaminocarboxylic acid chelate compounds, crosslinked polyvinylpyrrolidones, maleic acid / styrene copolymers, methacrylic acid copolymers, and polyhydric alcohols. Examples thereof include a half ester of the polymer of the above and a dicarboxylic acid anhydride, a water-soluble salt of polystyrene sulfonic acid, polyoxyethylene alkanediols, polyoxyethylene alkyndiols, alkynediols and the like.

As the spreading agent, various surfactants such as sodium dialkyl sulfosuccinate, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene fatty acid ester; paraffin, terpene, polyamide resin, polyacrylic acid salt, etc. , Polyoxyethylene, wax, polyvinylalkyl ether, alkylphenol formalin condensate, synthetic resin emulsion and the like.

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

Examples of the anti-caking agent include polysaccharides such as starch, alginic acid, mannose, and galactose; polyvinylpyrrolidone, white carbon, ester gum, petroleum resin, and the like.

Examples of the disintegrant include sodium tripolyphosphate, sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, copolymer of methacrylic acid ester, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene / isobutylene / maleine anhydride. Examples thereof include acid copolymers and starch / polyacrylonitrile graft copolymers.

Examples of the decomposition inhibitor include desiccants such as zeolite, quicklime, and magnesium oxide; antioxidants such as phenol-based, amine-based, sulfur-based, and phosphoric acid-based; ultraviolet absorbers such as salicylic acid-based and benzophenone-based. Can be mentioned.

Examples of the preservative include potassium sorbate, 1,2-benzthiazoli-3-one and the like.

Examples of plant pieces include sawdust, palms, corn cobs, tobacco stems, and the like.

On the other hand, when the above-mentioned additive component is contained in the herbicide of the present invention, the content ratio thereof is usually 5 to 95%, preferably 20 to 90% for a carrier such as a solid carrier or a liquid carrier on a mass basis. The surfactant is usually selected in the range of 0.1 to 30%, preferably 0.5 to 10%, and the other additives are selected in the range of 0.1 to 30%, preferably 0.5 to 10%.

The herbicide of the present invention includes powders, powders and granules, granules, wettable powders, aqueous solvents, granule wettable powders, tablets, jumbo agents, emulsions, oils, oily suspensions, liquids, flowable agents, emulsions, and Microemulsion agent, Suspension emulsion agent, Micro-spray agent, Microcapsule agent, Jumbo agent, Bean crush <registered trademark> agent, Smoke agent, Aerosol agent, Bait agent, Paste agent, Foam agent, Carbon dioxide gas preparation, Paint, It is used by formulating it into any dosage form such as wood protective paint and sealing agent.

In the actual use of these preparations, they can be used as they are, or they can be diluted to a predetermined concentration with a diluent such as water. The application of various formulations or dilutions thereof containing the compounds of the present invention is usually a commonly used application method, that is, spraying (eg, spraying, misting, atomizing, dusting, granulation, water surface application, etc.). Box application, etc.), soil application (eg, contamination, irrigation, etc.), surface application (eg, coating, powder coating, coating, etc.), seed treatment (eg, smear, powder coating treatment, etc.), immersion, poison bait, smoke It can be done by application or the like.

The pesticide composition of the present invention can be used by spraying foliage, soil application, water surface application, or the like. The pesticide composition of the present invention, particularly a herbicide, is used in soil, especially in upland fields or paddy fields where useful plants are cultivated.

In the pesticide composition of the present invention, the blending ratio of the active ingredient is appropriately selected as needed, but in the case of powder or granules, 0.01 to 10% (weight), preferably 0.05 to 5 It is better to select from the range of% (weight) as appropriate. In the case of an emulsion or a wettable powder, it is preferable to appropriately select from the range of 1 to 50% (weight), preferably 5 to 30% (weight). Further, in the case of a flowable agent or an oil suspension agent, it is preferable to appropriately select from the range of 1 to 40% (weight), preferably 5 to 30% (weight).

The application rate of the pesticide composition of the present invention varies depending on the type of compound used, target weeds, development tendency, environmental conditions, dosage form used, and the like. For example, when the pesticide composition of the present invention is used as a herbicide as it is, such as powders and granules, the active ingredient may be appropriately selected from the range of 1 g to 50 kg, preferably 10 g to 10 kg per hectare. .. Further, when it is used in a liquid state such as in the case of making an emulsion, a wettable powder, a flowable agent or the like, it is preferable to appropriately select from the range of 0.1 to 50,000 ppm, preferably 10 to 10,000 ppm.

In addition to the compound of the present invention, the pesticide composition of the present invention also contains at least one other pesticide active ingredient, for example, another disease control agent component, an insecticide component, an acaricide component, and the like. Formulated, mixed or mixed with insecticide components, cooperating agent components, attractant components, repellent components, herbicides components, pesticide components, microbial pesticide components, plant growth regulator components, fertilizers, soil improvers, etc. It may be used together.

When mixed or used in combination with other pesticide active ingredients or fertilizers, the preparations of each single ingredient can be mixed and used at the time of application. Further, each of the individual individual components may be used sequentially, or may be applied after a few days. When the application is performed after a certain number of days, the treatment may be performed at intervals of about 1 to 40 days, although it depends on other components used.

In the pesticide composition of the present invention, at least one compound selected from the fused heterocyclic derivative represented by the general formula [I] and an agriculturally acceptable salt, and at least one selected from other pesticide active ingredients. When the above is mixed and applied, it is usually applied at a mass ratio of 100: 1 to 1: 100, preferably 20: 1 to 1:20, particularly 10: 1 to 1:10.

The compounding ratio (mass%) of the active ingredient in the pesticide composition of the present invention is appropriately selected as necessary. For example, in the case of a powder, a powder or granule, a fine granule, etc., it is preferable to appropriately select from the range of 0.01 to 20%, preferably 0.05 to 10%, and in the case of a granule, etc., 0.1 to It is preferable to appropriately select from the range of 30%, preferably 0.5 to 20%, and in the case of a wettable powder, granule wettable powder, etc., appropriately select from the range of 1 to 70%, preferably 5 to 50%. It is preferable to select from the range of 1 to 95%, preferably 10 to 80% in the case of an aqueous solvent, a liquid agent, etc., and 5 to 90%, preferably 10 to 80% in the case of an emulsion or the like. It is better to select from the range as appropriate, and it is better to select from the range of 1 to 50%, preferably 5 to 30% when using an oil agent, an oily suspending agent, etc., and 5 to 60% when using a flowable agent, etc. , It is preferable to appropriately select from the range of 10 to 50%, and in the case of an emulsion agent, microemulsion agent, suspo emulsion agent, etc., it is preferable to appropriately select from the range of 5 to 70%, preferably 10 to 60%. Often, in the case of tablets, bait agents, pastes, etc., it is better to appropriately select from the range of 1 to 80%, preferably 5 to 50%, and in the case of fumigants, etc., 0.1 to 50%. It is preferable to appropriately select from the range of 1 to 30%, and in the case of an aerosol agent or the like, it is preferable to appropriately select from the range of 0.05 to 20%, preferably 0.1 to 10%.

These formulations are diluted to an appropriate concentration and sprayed, or applied directly.

The pesticide composition of the present invention is generally applied at an active ingredient concentration of 0.1 to 5000 ppm when diluted with a diluent. When the preparation is used as it is, the application rate per unit area is 0.1 to 5000 g per ha as the active ingredient compound, but is not limited thereto.

It goes without saying that the pesticide composition of the present invention is sufficiently effective even when the compound of the present invention is used alone as an active ingredient, but other pesticides such as insecticides and acaricides are available as needed. Can be mixed or used with insecticides, synergists, fungicides, antiviral agents, attractants, herbicides, plant growth regulators, spreading agents, other agricultural materials, fertilizers, etc. In this case, it may show a better effect.

Next, known herbicide compounds, herbicidal active ingredients or plant growth regulator compounds which may be mixed or used in combination are exemplified below, but are not limited to these examples.

Herbicide compound or herbicidal active ingredient:
Ioxynil (including salts with lithium salt, sodium salt, octanonic acid, etc.), acronifen, achlorein, azafenidin, asifluorfen (including salts with sodium, etc.) ), Azimsulfuron, ashlum, acetochlor, atrazine, anilophos, amicarbasone, amidosulfuron, amidosulfuron, amidosulfuron. Chlor (aminocyclopyrachlor), aminopyrlide, amiprophos-methyl, amethrin, atrazine mosaic virus (Araujia Mosaic Viras), arachlor (Including salts with sodium and the like), ancymidol, isouron, isoxachlortole, isoxaflutole, isoxaben, isodecyl alcohol ethoxylate (isodecylcoltole) ), Isoproturnon, ipfencarbazone, imazaquin, imazapic (including salts with amines, etc.), imazapyr (containing salts such as imazapyr) (isopropylamine and the like). ｉｍａｚａｍｅｔｈａｂｅｎｚ）、イマザメタベンズ・メチル（ｉｍａｚａｍｅｔｈａｂｅｎｚ－ｍｅｔｈｙｌ）、イマザモックス（ｉｍａｚａｍｏｘ）、イマゼタピル（ｉｍａｚｅｔｈａｐｙｒ）、イマゾスルフロン（ｉｍａｚｏｓｕｌｆｕｒｏｎ）、インダジフラム（ｉｎｄａｚｉｆｌａｍ）、インダノファン（ｉｎｄａｎｏｆａｎ）、エグリナジン・エチル（ｅｇｌｉｎａｚｉｎｅ－ｅｔｈｙｌ）、エスプロカルブ（ｅｓｐｒｏｃａｒｂ） ,workman Tamethosulfuron-methyl, ethalfururalin, ethidimuron, ethoxysulfuron, ethoxyphen, ethoxyphen, ethoxyphenethyl , Etobenzanid, epilifenasyl, endotal disodium, oxadiazon, oxadiargyl, oxadialgyl, oxadiargyl, oxadichlorofen Oryzalin, Obuda Pepper Virus, orthosulfamuron, orbencarb, oleic acid, oleic acid, caprylic acid, caprylic acid, caprylic acid, caprylic acid, acid), carfentrazone-ethyl, carbutylate, carbetamide, quizalofop, quizalofop-ethyl, quizalofop-ethyl, quizalofop-ethyl ), Quizalofop-P-tefuryl, Xanthomonas campestris, quinocramine, quinchlorac, quinclocyl, quinclycyl ), Clacyfos, glyphosate (sodium, potassium, amine, propylamine, isopropylamine, ammonium, isopropylammonium, guanidine, monoethanolamine, choline, BAMPA (N, N-bis- (aminop)). Lopil) Methylamine), dimethylamine or trimesium and other salts), glufosinate (including amine or sodium and other salts), glufosinate-P, glufosinate-P.sodium salt (glufosinate-) P-sodium, colletotric, clodinahop, clodinahop-propargyl, clopyrlide (including monoethanolamine salt), chromophen (Clomeprop), colletotrichum-methyl, chloramben, chloridazon, chlorimuron, chlorimuron-ethyl, chlorsulfuron-thyl, chlorsulfuron. dimethyl, chlorthiamid, chlorphthalim, chlorflurenol-methyl, chlorpropham, chlorpropham, chlorbromron, chlorbromron, chlorochromon, chlorochloron Dox (ketospiradox) (including salts such as sodium, calcium or ammonia), Colletotrichum orbiculare, Colletotrichum gloeospolyeuides (Collettrichum gloeosporioides), Colletotrichum Saflufenacil, salmentine, cyanazine, cyanamide, diuron, diethatill-eth yl), dioxopyridrione, dicamba (amines, diethylamines, isopropylamines, diglycolamines, dimethylammoniums, diolamines, isopropylammoniums, auramines, potassium, tralolamines, BAPMA (N, N-bis). -(Aminopropyl) methylamine), salts such as choline, sodium or lithium, or esters such as methyl ester), cycloate, cycloxydim, diclosulum, cyclosulfamuron. , Cyclopyranil, cyclopyrimorate, dichlobenil, diclohop, diclohop-P-methyl, diclohop-methyl, diclohop-methyl. Dichlolrop), dichlolprop-P (including salts such as dimethylammonium, potassium, sodium, choline, or esters such as butothyl ester, 2-ethylhexyl ester, isoctyl ester, methyl ester), diquat. (Diquat), diquat dibromide, dithiopyr, siduron, dinitramine, cinidon-ethyl, cinosulfone (cinosulfuron), cinosulfuron (cinosulfuron) Includes), dinoterb, cihalohop, cyhalohop-butyl, cypyrafluone, diphenamide, diphenzocoat, diphenzocoat, diphenzoqut. Shimazine, dimesulfazet, dimethachlor, dimethametrin, dimethenamide ), Dimethenamide-P, simethrin, dimepiperate, dimefuron, Pseudomonas fluorescens, symmetry, symmetry, symmetry, symmetry, , Sulfentrazone, sulfosate, sulfosulfuron, sulfomethuron-methyl, setoxydim, selerothinia minor (Selerothinia) daimuron, taxomin A, tobacco mild green mosaic tobamovirus (Tobacco Mild Green Mosaic Tobamovirus), tobacco rattle virus (Tobacco Rattle Virus), darapon (dalapon) thiencarbazone (including sodium salt, methyl ester, etc.), thiocarbazil, thiobencarb, thijiazimin, thidiazuron, thifensulfuron, thifensulfuron , Desmedipham, desmetriline, tetflupyrolimet, tenylchlor, tebutam, tebuthiuron, tebuthiuron, tebuthiuron, tebuthiuron, tebuthiuron, tebuthiuron, tebuthiuron, tebuthiuron Terbutyrazine, terbutrin, terbumeton, tembotrione, tobamozone, tralkoki Sididim, triaziflam, triasulfuron, triafamone, tri-allate, trietazine, trichloropill, trichloropyr, trichloropyr Trimethylammonium, tritosulfuron, tripyrasulfone, trifludimoxazin, triflusulfuron, triflulufuron, triflusulfuron, triflusulfuron, triflusulfuron. (Trifluorixylfuron) (including salts such as sodium), trivenuron-methyl, tropyllate, naptalam (including salts with sodium etc.), naproanilide (naproanilide), napropamide, napropamide. , Napropamide-M, nicosulfuron, lactic acid, nebulon, norflurazon, barkholderia linogensis (Barkholderia paraquat) paraquat ), Paraquat dichloride, halauxifen, halauxifen-benzyl, halauxifen-methyl, halauxifen-methyl, barcorderia linogensis (Burk) Benzylphop-P, Benzylhop-etothyl, Benzylhop-P-methyl, halosafen, halosulfuron -Methyl, bixlozone, picloram (including salts with dichloroammonium, traroamine, etc.), picolinaphen, bicyclopyrone, bispiribac-sodium. pinoxaden, bipyrazone, biphenox, piperophos, pyraclonil, pyrasulfotore, pyrazolfotole, pyrazoxylonate, pyrazoxylone, pyrazoxyl) (Bilanafos), pyraflufen, pyraflufen-ethyl, pyridafol, pyrithiobac-sodium, pyridate, pyritide, pyriphthalide, pyriftalib (pyridate). pyribenzaxim, pyrimisulfan, pyriminobac-methyl, pyroxasulfone, pyroxslum, phytopsola palmiphorn, phytophylon Sulfone, fenoxaprop (including methyl, ethyl, isopropyl ester), phenoxaprop-P (including methyl, ethyl, isopropyl ester), fenquinotrione, Fentiaprop-ethyl, fentrazamide, fenpyrazone, phenmedifam, former kenopodicola, former Helbarum, Forma macrostomah, Butachlor, butafenacil, butamifos, butylate, puccinia canalicula, puccinia canalicula Butenachlor, butralin, butroxydim, frazasulfuron, flamprop (including methyl, ethyl, isopropyl ester), flamprop-M (methyl). Ethyl, including isopropyl ester), primisulfuron, primisulfuron-methyl, fluazihop-butyl, fluazihop-P, fluazihop-P.butyl fluazifop-P-butyl, fluazolate, fluomethuron, fluoroglycophen-ethyl, flucarbazone-sodium, flucarbazone-sodium, flucuronle-flu of Fluthiaset-methyl, flupyrsulfuron-methyl (including salts such as sodium, calcium or ammonia), flufenacet, flufenpyr-ethyl, full Propanate (including sodium salt), flupoxame, flumioxazine, flumiclorac-pentyl, flumethzulum, flulydone, flulydone, fluridone, flulydone. (Fluroxypyr) Esters such as tomethyl and meptyl, or salts such as sodium, calcium and ammonia), flurochloridone, pretilachlor, procarbazone (including salts with sodium etc.), prodiamine (including salts with sodium etc.) Prodiamine, Prosulfuron, Prosulfocarb, Propazinehop, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine. , Propyrisulfuron, propham, profluazol, prohexadione-calcium, propoxycarbazone, propoxycarbazone, sodium propoxycarbazone, sodium , Propoxydim, bromoxynil, brompyrazon, promethrin, promethon, bromoxynil (including bromophenil, butyric acid, octanoic acid or heptanic acid). bromoxynil, bromoxynil, floramulam, florpyrauxifen, florpyrauxifen-benzyl, floryrauxifen-benzyl, hexadinone (hexazinone) Ethyl (benazolin-ester), penoxyslam (penoxmulam), pepino mosaic virus (Pepino Mosaic Virus), heptamaloxyloglucan (heptamaloxyloglucan), beflubutamide (beflubult) (Pela rgonic acid, bencarbazone, benquitrione, benzfendizone, bensulide, bensulfuron, bensulfuron, bensulfuron-methyl, bensulfuron-methyl. Benzophenap, bentazone, pentanochlor, pendimethalin, pentoxazone, benfururalin, benfururalin, benefuresamine, benfuresate , Foramsulfuron, forchlorphenuron, mecoprop (sodium, potassium, isopropylamine, triethanolamine, dimethylamine, diolamine, traroamine, salts of choline, etc., or etadir Contains esters such as esters, 2-ethylhexyl esters, isoctyl esters, methyl esters, etc.), mecoprop-P-potassium, mesosulfuron (including esters such as methyl), mesotrione. ), Metazachlor, metazosulfuron, methabenzthiazuron, metamitron, metamihop, sodium metham, sodium salt, etc. (DSMA), methiozolin, methyldymuron, metoxuron, metoslum, metsulfuron-methyl, metulfuron-methyl, metobromeron, metobromeron Methylbuzin, mepicote chloride (m) epiquat chloride, mefenacet, monosulfuron (including methyl, ethyl, isopropyl ester), monolinuron, molinate, iodosulfuron, iodosulfuron-sodium salt. -Sodium), iofensulfuron, iofensulfuron sodium salt (iofensulfu)
ron-sodium, lactophen, lancotrione, linuron, rimisoxafen, rimsulfuron, lenacyl, 2,2,2-trichloroacetic acid (TCA) (sodium) , Contains salts such as calcium or ammonia), 2,3,6-trichlorobenzoic acid (2,3,6-TBA), 2,4,5-trichlorophenoxyacetic acid (2,4,5-T), 2, , 4-Dichlorophenoxyacetic acid (2,4-D) (amine, diethylamine, triethanolamine, isopropylamine, dimethylammonium, diolamine, dodecylammonium, heptylammonium, tetradecylammonium, triethylammonium, tris (2-hydroxypropyl) ) Salts such as ammonium, tralolamine, choline, sodium or lithium, or butothyl esters, 2-butoxypropyl esters, 2-ethylhexyl esters, methyl esters, ethyl esters, butyl esters, isobutyl esters, octyl esters, pentyl esters, propyls. Includes esters such as esters, isoctyl esters, isopropyl esters, meptyl esters, tefryl esters, etc.), 2,4-dichlorophenoxybutyric acid (2,4-DB) (amines, diethylamines, triethanolamines, isopropylamines, etc.) Contains salts such as dimethylammonium, choline, sodium or lithium, or esters such as isoctyl esters), 2-amino-3-chloro-1,4-naphthoquinone (ACN), 2-methyl-4-chlorophenoxyacetic acid (including 2-methyl-4-chlorophenoxyacetic acid). MCPA) (including salts such as sodium, dimethylammonium and choline, or esters such as 2-ethylhexyl ester, isoctyl ester and ethyl ester), 2-methyl-4-chlorophenoxybutyric acid (MCPB) (sodium salt, etc.) (Including ethyl esters, etc.), 4- (2,4-dichlorophenoxy) butyric acid (2,4-DB), 4,6-dinitro-O-cresol (DNOC) (including salts such as amine or sodium), ( 5S) -3- (3,5-difluorophenyl) -N- [rel- (3R, 5R) -5- (trifluoromethylsulfonylcarbamoyl) terrorahydrofuran-3-yl] -5-vinyl-4H-isoxazole -5-Carbo Xyamide ((5S) -3- (3,5-dihydrofuranyl) -N- [rel- (3R, 5R) -5- (trifluoromethylcarbamoyl) tetrahydrofuran-3-yl] -5-vinyl-4H-isoxazole (Chemical name, CAS registration number: 2266183-40-6) (International Publication No. 2018/228896, International Publication No. 2020/114934), N4- (2,6-dihydrophenyl) -6- (1) -Fluoro-1-methylethyl) -1,3,5-triazine-2,4-diamine (N4- (2,6-dihydrofurenyl) -6- (1-fluoro-1-methyltyl) -1,3,5 -Triazine-2,4-diamine) (Chemical name, CAS registration number: 1606999-43-2) (International Publication No. 2014/064094, International Publication No. 2015/162164), (5S) -3- ( 3,5-Difluorophenyl) -N- [(3R) -5- (methylsulfonylcarbamoyl) -2,3-dihydrofuran-3-yl] -5-vinyl-4H-isoxazole-5-carboxyamide ((5S) ) -3- (3,5-dihydrofuranyl) -N-[(3R) -5- (methylsulfonylcarbamoyl) -2,3-dihydrofuran-3-yl] -5-vinyl-4H-isoxazole-5-carboxamide) (Chemistry) Name, CAS Registration Number: 2266190-06-9) (International Publication No. 2018/228896, International Publication No. 2020/114934), (5R) -3- (3,5-dihydrophenyl) -5-methyl -N- [rel- (3R, 5R) -5- (methylsulfonylcarbamoyl) tetrahydrofuran-3-yl] -4H-isoxazole-5-carboxyamide ((5R) -3- (3,5-dihydrofurenyl) -5 -Methyl-N- [rel- (3R, 5R) -5- (methylfurfonylcarbamoyl) tetrahydrofuran-3-yl] -4H-isoxazole-5-carboxamide (chemical name, CAS registration number: 2266164-36-5) International Publication No. 2018/228986, Publication No. 2020/114934), (5R)- 3- (3,5-difluorophenyl) -N-[(3R) -5- (methoxycarbamoyl) -2,3-dihydrofuran-3-yl] -5-methyl-4H-isoxazole-5-carboxyamide ( (5R) -3- (3,5-difluorophenyl) -N-[(3R) -5- (methoxycarbamoyl) -2,3-dihydrofuran-3-yl] -5-methyl-4H-isoxazole-5-carboxamide) (Chemical name, CAS registration number: 2266170-31-2) (International Publication No. 2018/228896, International Publication No. 2020/114934), 4-Hydroxy-1-methyl-3- [4- (trifluoro) Methyl) -2-pyridyl] imidazolidine-2-one (4-hydroxy-1-methyl-3- [4- (trifluoromethyl) -2-pyridyl] imidazolidin-2-one) (chemical name, CAS registration number: 1708087) -22-2) (International Publication No. 2015/059262, International Publication No. 2018/015476), 6- (1-fluorocyclopentyl) -N4- (2,3,5,6-tetrafluorophenyl)- 1,3,5-triazine-2,4-diamine (6- (1-fluorochemical group) -N4- (2,3,5,6-tetrafluorophenyl) -1,3,5-triazine-2,4-diamine) (Chemical name, CAS registration number: 182807-75-7) (International Publication No. 2015/162164), 6- (1-fluoro-1-methylethyl) -N4- (2,3,5,6-tetra) Fluorophenyl) -1,3,5-triazine-2,4-diamine (6- (1-fluoro-1-methylyl) -N4- (2,3,5,6-tellafluorophenyl) -1,3,5- Triazine-2,4-diamine) (Chemical name, CAS registration number: 1606999-21-6) (International Publication No. 2014/064094, International Publication No. 2015/162164), (5S) -3- (3) -Fluoro-5-methylphenyl) -N- [rel- (3R, 5R) -5- (methoxycarbamoyl) tetrahydrofuran-3-yl] -5-vinyl-4H-isoxazole-5-carboxyamide ((5S)- 3- (3-fluoro-5-methylph) nyl) -N- [rel- (3R, 5R) -5- (methoxycarbamoyl) tetrahydrofuran-3-yl] -5-vinyl-4H-isoxazole-5-carboxamide (chemical name, CAS Registry Number: 2266292-43-) 5) (International Publication No. 2018/228896, International Publication No. 2020/114934), 6- (1-Methylcyclobutyl) -N4- (2,3,5,6-tetrafluorophenyl) -1, 3,5-Triazine-2,4-diamine (6- (1-methylcyclobutyl) -N4- (2,3,5,6-terafluorophenyl) -1,3,5-triazine-4,4-diamine) (Chemistry) Name, CAS Registry Number: 1607001-97-7) (International Publication No. 2014/064094, International Publication No. 2015/162164), AE-F-150944 (code number), IR-6396 (code number), MCPA-thioethyl, SYS-298 (code number), SYS-300 (code number), S-ethyldipropylthiocarbamate (EPTC), S-metholachlor, S-9750 ( Code number), MSMA (MSMA), HW-02 (code number).

Plant growth regulator:
1-naphthylacetamide, 1-methylcyclopropene, 1,3-diphenylurea, 2,3,5-triiodobenzoic acid (2,3,5) -Triiodobenzoic acid), 2-methyl-4-chlorophenyloxybutyric acid (MCPB) [including sodium salts, ethyl esters, etc.], 2- (naphthalene-1-yl) acetic acid (2- (naphthalene-1-yl) aceticide) , 2,6-diisopropylnaphthalene, 3-[(6-chloro-4-phenylquinazoline-2-yl) amino] propan-1-ol (3-[(6-chloro-4-) phenylquinazoline-2-yl) amino] propane-1-ol), 4-oxo-4- (2-phenylethyl) aminobutyric acid (chemical name, CAS registration number: 1083-55-2), 4-chlorophenoxyacetic acid ( 4-CPA), 5-aminolevulinic acid chloride, 5- (trifluoromethyl) benzo [b] methyl thiophen-2-carboxylate (Methyl 5- (trifluoromethyl) beno [b] thiofen- 2-carboxylate, AVG (aminoethoxyvinylglycine), n-decyl alcohol (n-decanol), anisiflupurin, aviglicine, aviclycine, ancimidol (ancymidol), abisicyl acid , Inabenfide, indole acetic acid, indole butylic acid, uniconazole, uniconazole-P, uniconazole-P, echothethe ), Epocholone, calcium chloride, choline chloride e), oxine-sulfate, kinetin, calcium peroxide, carbone, calcium formate, cloxyphonac, potassium salt. (Cloxyphonac-potassium), cloprop, chlormecoat, chlormequart-chloride, chloropropham, choline, cytokine, acid, cytosylde , Cyanamide, sodium cyanate, cyclonilide, dichlolrop (salts such as dimethylammonium, potassium, sodium, choline, etc., or butothyl esters, 2-ethylhexyl esters, isoctyl). Esters, including esters such as methyl esters), dichlorprop-P (including salts such as sodium, potassium, dimethylammonium, or 2-ethylhexyl esters), diquat, diquat dibromide. (Diquat dibromide), dikegulac, gibberellic acid, gibberellin A4, gibberellin A7, gibberellin A7, gibberellin A7, dimethine cis-jasmone), jasmonic acid, methyl jasmonate, streptomycin, calcium polysulfide, calcium polysulfide, diminodicide -1-ol (decan-1-ol), triacontanol, tripentenol (tri) apenthenol), trinexapac-ethyl, tribufos, paclobutrazol, paraffin, bispiribac-sodium, himexazole ), Fluthiaset-methyl, pyraflufen-ethyl, flumethralin, flupurrimidol, flurenol, pronitridin, pronitridin, pronitridin Prohexadione-calcium, heptamaloxyloglucan, 6-benzylaminopurine, pendimethalin, phorchlorphenuronfuronner ), Maleic hydrazide, mepicut chloride, mefluidide, lipochitooligosaccharides, for example lipochitoorganesarcsides.

Next, known phytotoxicity-reducing compounds that may be mixed or used in combination are exemplified below.

Isoxadiphen, isoxadiphen-ethyl, oxabetrinil, octane-1,8-diamine (octane-1,8-diamine), cloquintocet, cloquintocet-cutcet. -Methyl, diethlate, cyometrinil, dichlormid, dicyclonone, cyprosulfamide, dymulfamide, dimulon, adimulon, adimulon, naphtha, naphtha, naphthalon. Fenchlorazole, fenchlorazole-ethyl, fenchlorim, furilazole, fluxofenim, fluxofenim, fluluxorem, fluorazole, benocole Mephenate, mephenpyr, mefenpyr-ethyl, mefenpyr-diethyl, lower alkyl substituted benzoic acid, 2,2-dichloro-N- (1,3-dioxolane-) 2-Ilmethyl) -N- (2-propenyl) acetamide (PPG-1292), 2-dichloromethyl-2-methyl-1,3-dioxane (MG-191), 3-dichloroacetyl-2,2,5- Trimethyl-1,3-oxazolidine (R-29148), 4-dichloroacetyl-1-oxa-4-azaspiro [4.5] decane (AD-67), 4-carboxy-3,4-dihydro-2H-1 -Benzenepyran-4-acetic acid (CL-304415, code number), MON4660 (code number), metcamifen, N1, N2-diallyl-N2-dichloroacetylglycinamide (DKA-24, code number), 1-bromo -4-[(Chloromethyl) sulfonyl] benzene (CSB), 2-propenyl 1-oxa-4-azaspiroate [4,5] decane-4-carbodithioate (MG-838, code number), 3 -(Dichloroacetyl) -2,2-dimethyl-1,3-oxazolidine (R-288725, code number), R-29148 (code number), 1- (dichloroacetyl) azepane (TI-35, code number).

Next, known insecticidal agents (insecticide active ingredients), acaricides (mite-killing active ingredients), nematode-killing agents (nematode-killing active ingredients), and synergistic agent compounds (co-active ingredients) that may be mixed or used in combination. Ingredients) are illustrated below.

Insecticidal active ingredient, acaricidal active ingredient, nematode active ingredient, synergistic active ingredient:
Allethrin, azadiractin, azamethiphos, acinonapyr, azinphos-ethyl, azinphos-ethyl, azinphos-ethyl, azinphos-me (Acetoprole), acephate, azocyclotin, abamictin, afidopyropen, afoxolaner, afoxolaner, amidoflumet, amidoflumet, amidoflumet ), Aldicarb, allethrin [including d-cis-trans-forms, d-trans-forms], isazophos, isamidofos, isocarbothion, isocarbophos. , Isocycloceram, isofenphos-methyl, isoprocarb, epsilon-methoflutrin, epsilon-metoflutrin, epsilon-momufluorothrin ), Imidacloprid, imiprothrin, indazapyroxamet, indoxacarb, esfenvalerate, ethiofenvalerate, ethiofencarbe Ethylene dibromide, etoxazole, etofenprox, ethoprophos, etrimphos, emamectin in), emamectin benzoate, endosulfan, empenthrin, oxazosulfyl, oxamyl, oxydimethronmethyl, oxydemethon-methon- Omethoate, Nuclear polyhedrosis virus, cadusafos, kappa-tefluthrin, kappa-bifenthrin, kappa-bifenthrin, kappa-bifenthrin Disease virus (Granulosis virus), Carbaryl, Carbosulfan, Carbofuran, Gamma-BHC (gamma-BHC), Chlorpyrifos (xylylcarb), Chlorpyrifos (quinalphos) chinometryat, acute paralysis virus (Enterovirus), chlorpyrifos, cryolite, clothianidin, clofenthine, chlorphanlide, chromaphenodide, chromaphenolide Empenthrinfos, chlordane, chlorpyrifos, chlorpyrifos, chlorpyrifos-methyl, chlorpyrifos-methyl, chlorpyrifos-methyl, chlorphenapil, chlorfenthrin , Chlormephos, chlorpyrifosrin, Empenthrinfos, Iridovirus, cyazipyr, cyanophos, Diafenthiuron, diamidafos, cyantranliprole, cyetpyrafen, dienochlor, cyenopyranophos, cyenopyraphen (cyeno) Virus (Sigma virus), Cyclaniliprole, Cycloxaprid, diclotophos, dichlofenthion, cyclobutrifluthrin, cyclobutrifluthrin, cyclobutrifluthrin Dicloromezotiaz, dicofol, dicyclanil, disulfoton, dinotefuran, dinobuton, cyhalothrin, cyhalothrin, cyhalothrin, cyhalothrin, cyhalothrin. Includes], cyphenothrin [(1R) -trans-including body], cyfluthrin [including beta-body], diflubenzuron, cyflumethofen (cyflumethofen), difluthrin (cyfluthrin), difluthrin (cyfluthrin) ), Cyhexatin, cypermethrin [including alpha-form, beta-form, theta-form, zeta-form], dimpropyridaz, dimethyl-2,2,2-trichloro- 1-Hydroxyethylphosphonate (DEP), dimethylbinphos, dimethoate, dimefluthrin, jasmone, cis-jasmone, jasmonic acid (jasmonic acid) (Methyl jasmon ａｔｅ）、シラフルオフェン（ｓｉｌａｆｌｕｏｆｅｎ）、シロマジン（ｃｙｒｏｍａｚｉｎｅ）、スタイナーネマカーポカプサエ（Ｓｔｅｉｎｅｒｎｅｍａｃａｒｐｏｃａｐｓａｅ）、スタイナーネマクシダイ（Ｓｔｅｉｎｅｒｎｅｍａｋｕｓｈｉｄａｉ）、スタイナーネマグラセライ（Ｓｔｅｉｎｅｒｎｅｍａｇｌａｓｅｒｉ）、スピドキサマト（ｓｐｉｄｏｘａｍａｔ）、スピネトラム（ｓｐｉｎｅｔｏｒａｍ）、スピノサド（ｓｐｉｎｏｓａｄ）、スピロDiazinon, spirotetramat, spiropidion, spiromesifen, sulcofuron-sodium, sulcofuron-sodium, sulfurlamide, sulfuramide, sulfurlamid Diazinon, thiacloprid, thiamethoxam, thioxazafen, thiodicarb, thiocyclam, thiocylam, thiosultaps ), Thiclopridoflor, tetrachloranthraniliroll, tetrachlorvinphos, tetradifon, tetradifon, tetranitrylthrin, tetranylphosphor tetramethrin, tebupirimphos, tebufenozide, tebufenpyrad, tefluthrin, teflubenzuron, teflubenzuron, teflubenzuron, teflubenzuron, teflubenzuron , Terbufos, tralomethr in), transfluthrin, triazamate, triazophos, trichlorphon, trichoderma aspirellum, trichoderma aspirellum, trichoderma paecilomes (Trifluunfuronate), triflumuron, triflumezopyrim, trimetacarb, tolfenpyrad, nared, nared, nicotine, nicotine, nicotine, nicotine, nicotine, nicotine. nemadecin), Denso virus, novaluron, noviflumuron, paecilomyces lilacinus, Bacillus lylacinus, Bacillus bacillus, Bacillus, Bacillus, Bacillus, Bacillusレカニ（Ｖｅｒｔｉｃｉｌｌｉｕｍｌｅｃａｎｉｉ）、ハイドロプレン（ｈｙｄｒｏｐｒｅｎｅ）、パスツーリアニシザワイ（Ｐａｓｔｅｕｒｉａｎｉｓｈｉｚａｗａｅ）、パスツーリアペネトランス（Ｐａｓｔｅｕｒｉａｐｅｎｅｔｒａｎｓ）、バチルスアミロリケファシエンス（Ｂａｃｉｌｌｕｓａｍｙｌｏｌｉｑｕｅｆａｃｉｅｎｓ）、バチルスフィルムス（Ｂａｃｉｌｌｕｓｆｉｒｍｕｓ）、バチルススフェリカス（Ｂａｃｉｌｌｕｓｓｐｈａｅｒｉｃｕｓ） , Bacillus subtillis, Bacillus turingensis, an insect toxin produced by Bacillus turingiensis, Bacillus turingensis subspecies Isawai. Aizawai), Bacillus thuringiensis subspecies Islaelensis (Bacillus thuringiensis subsp. Islaelensis), Bacillus thuringiensis subspecies Kurstaki (Bacillus thuringie)
nsis subsp. Kurstaki), Bacillus thuringiensis subspecies Tenebrionis (Bacillus thuringiensis subsp. Halphenprox, halophenothrin, bioallethrin, bioallethrin S-cyclopentenyl, bioallethrin S-cyclopentenyl, biolesmethrin (biorethrin) DCIP), bistriflulon, hydramethylnon, biphenazete, biphenothrin, pyflubude, pyflubulude, piperonylbutoxide, piperonylbutoxide (piperon) Roll (pyrafluple), pyridaphenthion, pyridaben, pyridalyl, pyrifluququinazon, pyriproll, pyridifluor, pyriproxyphen (pyridiplo) Robin (pyriminostrobin), pyrimiphos-methyl, pyrethrin, famphur, fipronil, fenazaquin, phenaziphos, phenothrin, phenomiphos Phenothinocarb, phenothrin [including (1R) -trans-forms], fu Fenobucarb, fenthion, phentoate, fenvalerate, fempyroximate, fenbutatin oxide, fenpropatinzifenzifenzifenzifenzifen , Sulfone, sulfuryl fluoride, butocarboxim, butoxycarboxim, buprofezin, fenvalerate, fenvalerate Indolizine, fluazuron, fluensulfurone, fluopyram, sodium fluoroacetate, fluxamethamid, fluxamethyl, fluxamatelamide flucychloron, flucytrinate, flufurylfamide, fluthrin, fluvalinate [including tau-body], flupyrazifurone, flupyrodifluone, fluspirone Flufroll, flufenerim, fluphenoxystrobin, fluphenoxuron, fluhexafon, flubendiamide, fluphenmidide, fluphenimide , Fluralaner, flurimfen, prothiophos, protrifenbute , Flonicamid, propaphos, propargite, prohydrojasmon, prophenofos, brofuranilide, brophrinylide, profluthr ｆｌｏｍｅｔｏｑｕｉｎ）、ブロモプロピレート（ｂｒｏｍｏｐｒｏｐｙｌａｔｅ）、ヘキサチアゾクス（ｈｅｘｙｔｈｉａｚｏｘ）、ヘキサフルムロン（ｈｅｘａｆｌｕｍｕｒｏｎ）、ペキロマイセステヌイペス（Ｐａｃｉｌｉｍｙｃｅｓｔｅｎｕｉｐｅｓ）、ペキロマイセスフモソロセウス（Ｐａｅｃｉｌｏｍｙｃｅｓｆｕｍｏｓｏｒｏｃｅｕｓ）、ペキロマイセスリラキナス（Ｐａｅｃｉｌｏｍｙｃｅｓｌｉｌａｃｉｎｕｓ）、ヘプタフルスリン（ｈｅｐｔａｆｌｕｔｈｒｉｎ）、 Heptenophos, permethrin, benclothiaz, benzpyrimoxan, bensultap, benzoximate, benzoximate, benzoximate, benzoximate Ｐｏｃｈｏｎｉａｃｈｌａｍｙｄｏｓｐｏｒｉａ）、ボーベリアテネーラ（Ｂｅａｕｖｅｒｉａｔｅｎｅｌｌａ）、ボーベリアバッシアーナ（Ｂｅａｕｖｅｒｉａｂａｓｓｉａｎａ）、ボーベリアブロンニアティ（Ｂｅａｕｖｅｒｉａｂｒｏｎｇｎｉａｒｔｉｉ）、ホキシム（ｐｈｏｘｉｍ）、ホサロン（ｐｈｏｓａｌｏｎｅ）、ホスチアゼート（ｆｏｓｔｈｉａｚａｔｅ）、ホスチエタン（ｆｏｓｔｈｉｅｔａｎ）、ホスファミドン（ｐｈｏｓｐｈａｍｉｄｏｎ）、 Phosmet, polynactins, formethantate, phorate, machine oil, malathion, milbemectin, mecarbam, mecarbam, mecarbam. (Methomyl), Me Taaldehyde (metaldehyde), metaflumizone, methamidophos, metham, methiocarb, methidiathion, methylisothiocionate, methylisothiocyanate (methyliso) , Metoxyphenozide, methotrin, metoflutrin, methoprene, metolcarb, mevinphos, meperfluthrium Monacrosporium phymatophagum, monocrotophos, momfluorothrin, Trichoderma harzianum, Littlea A (litlure-A), Little aluminum (litlure-A), Little aluminum (litlure-A), Little aluminum (litlure-A) Zinc (zinc phosphide), hydrogen phosphide (phosphide), rufenuron, rescalure, resmethrin, repimeticin, rotenone, rothenone, cytoplasmic corpose virus-embedded virus. virus), fenbutatin oxide, calcium cyanide, organic tin compounds, nicotine-sulfate, (Z) -11-tetradecenyl-acetate, (Z) -11-hexadecenate, (Z) -11-hexadecenate. (Z) -11-hexadecenyl = acetate, (Z) -9,12-tetradecadienyl = acetate, (Z) -9-tetradecene-1-ol, (Z, E) -9,11-tetradecadi Enil-acetate, (Z, E) -9,12 -Tetradecadienyl-acetate, 1,1,1-trichloro-2,2-bis (4-chlorophenyl) ethane (DDT), 1,3-dichloropropene (1,3-dichloropropene), 4,6-dinitro -O-Cresol (DNOC), Bt protein (Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1), methyleugenol, 4- (p-acetooxyphenyl) -2-butanone, (Z) -10-Tetradecenyl = acetate, (E, Z) -4,10-tetradecazineiel = acetate, (Z) -8-dodecenyl = acetate, (Z) -11-tetradecenyl = acetate, (Z) -13- Icosen-10-on, 14-methyl-1-octadecene, AKD-1193 (code number), BCS-AA10147 (code number), CL960167 (code number), O, O-dichloro-O- [4- (dimethylsul) Phenyl) phenyl] -phosphorothionate (DSP), O-ethyl-O-4- (nitrophenyl) phenylphosphonothioate (EPN), RU15525 (code number), XMC (XMC), Z-13-icosen -10-on, ZXI8901 (code number), F4260 (code number).

Next, known bactericidal agents (bactericidal active ingredients) or disease control agent compounds that may be mixed or used in combination are exemplified below.

Bactericidal active ingredient or disease control agent compound:
Agrobacteria radiobacter, azaconazole, acibenzolar-S-methyl, azoxystrobin, azoxystrobin, anilazine, anilazine aminopylifen, amethoctadine, aldimorph, isotianil, isopyrazam, isofetamid, isofetamide, isofluciplam, isoflucypla ipflufenoquin, ipfentrifluconazole, iprodione, iplovalicarb, iprobenfos, imazaryl, iminoctadine, iminoctadine, iminoctadine, iminoctadine , Imibenconazole, impylfluxam, imprimatin A, imprimatin B, edifenphos, edifenphos, etaconazol, etaconaz (Ethirimol), ethoxyquin (ethoxyquin), etridiazole, enestrovulin, enoxastrobin, epoxyconazole, organic oil, organic oil, organic oil. Zol (oxazinylazole), oxathiapiprolin, oxycarboxin, oxyquinoline copper (oxine-copper), oxytetracyclate Phosphorus (oxytellacycline), oxypoconazole-fumarate, oxolinic acid, copper dioctanoate, octylinone, octylinone, octyrinone, of Phenol (o-phenylphenol), Kasugamycin, Captafol, Carpropamide, Carbendazim, Carboxin, Carboxine, Candida, Candida, Candida, Candida, Candida, Candida, Candida. Candida saitoana, quinoxyphen, quinofumelin, quinomethionat, captan, quinconazole, quinconazole, quintozen, quintozen, quintozen, quintozene coumethoxystrobin, coumoxystrobin, gliocladium catenulatum, cryptococcus albidas, cryptococcus albidos, cresoxym-methyl (kreso)クロゾリネート（ｃｈｌｏｚｏｌｉｎａｔｅ）、クロロインコナジド（ｃｈｌｏｒｏｉｎｃｏｎａｚｉｄｅ）、クロロタロニル（ｃｈｌｏｒｏｔｈａｌｏｎｉｌ）、クロロネブ（ｃｈｌｏｒｏｎｅｂ）、ケトミウムクプレウム（Ｃｈａｅｔｏｍｉｕｍｃｕｐｒｅｕｍ）、コニオシリウムミニタンス（Ｃｏｎｉｏｔｈｙｒｉｕｍｍｉｎｉｔａｎｓ）、シアゾファミド（ｃｙａｚｏｆａｍｉｄ）、ジエトフェンカルブ（ｄｉｅｔｈｏｆｅｎｃａｒｂ）、ジクロシメット（ｄｉｃｌｏｃｙｍｅｔ） , Dichlofluandid, Dichlobenchazox (dichlob) entiazox, dichromezine, dichloran, dichlorophen, dithianon, diniconazole, diniconazol M (diniconazole-m), dinicozole-m ｄｉｐｙｍｅｔｉｔｒｏｎｅ）、ジフェニルアミン（ｄｉｐｈｅｎｙｌａｍｉｎｅ）、ジフェノコナゾール（ｄｉｆｅｎｏｃｏｎａｚｏｌｅ）、シフルフェナミド（ｃｙｆｌｕｆｅｎａｍｉｄ）、ジフルメトリム（ｄｉｆｌｕｍｅｔｏｒｉｍ）、シプロコナゾール（ｃｙｐｒｏｃｏｎａｚｏｌｅ）、シプロジニル（ｃｙｐｒｏｄｉｎｉｌ）、シメコナゾール（ｓｉｍｅｃｏｎａｚｏｌｅ）、ジメチリモル（ｄｉｍｅｔｈｉｒｉｍｏｌ）、ジメチルジスルフィド（ｄｉｍｅｔｈｙｌｄｉｓｕｌｆｉｄｅ）、ジメトモルフ（ｄｉｍｅｔｈｏｍｏｒｐｈ）、シモキサニル（ｃｙｍｏｘａｎｉｌ）、ジモキシストロビン（ｄｉｍｏｘｙｓｔｒｏｂｉｎ）、シュードザイマフロクローサ（Ｐｓｅｕｄｏｚｙｍａｆｌｏｃｃｕｌｏｓａ）、シュードモナスオーレオファシエンス（Ｐｓｅｕｄｏｍｏｎａｓａｕｒｅｏｆａｃｉｅｎｓ）、シュードモナスクロロラフィス（Ｐｓｅｕｄｏｍｏｎａｓｃｈｌｏｒｏｒａｐｈｉｓ）、シュードモナスシリンガエ（Ｐｓｅｕｄｏｍｏｎａｓｓｙｒｉｎｇａｅ ), Pseudomonas fluorescens, Pseudomonas rhodesiae, ziram, silthiofam, zucchini yellow spot mosaic virus attenuated strain (Zucini) Glyceoviridis, Pseudomonas lygicus, Pseudomonas spiroxamine, Pseudomonas, sedaxane, sevoctylamin Talaomyces flavus, tiadinil, thiabendazole, thiram, thiophanate, thiophanate-methyl, thiophanate-methyl, tifluzamid , Tecloftalam, tetraconazole, debacarb, tebuconazole, tebufloquin, terbinafine, terbinafine, dodin (terbinafine), dozin (dodin)トリアジメホン（ｔｒｉａｄｉｍｅｆｏｎ）、トリアゾキシド（ｔｒｉａｚｏｘｉｄｅ）、トリクラミド（ｔｒｉｃｈｌａｍｉｄｅ）、トリクロピリカルブ（ｔｒｉｃｌｏｐｙｒｉｃａｒｂ）、トリコデルマアスペレラム（Ｔｒｉｃｈｏｄｅｒｍａａｓｐｅｒｅｌｌｕｍ）、トリコデルマアトロビリデ（Ｔｒｉｃｈｏｄｅｒｍａａｔｒｏｖｉｒｉｄｅ）、トリコデルマガムシイ（Ｔｒｉｃｈｏｄｅｒｍａｇａｍｓｉｉ）、トリコデルマ・ストロマチカム（Ｔｒｉｃｈｏｄｅｒｍａｓｔｒｏｍａｔｉｃｕｍ）、トリコデルマパエキロマイセス（Ｔｒｉｃｈｏｄｅｒｍａｐａｅｃｉｌｏｍｙｃｅｓ）、トリコデルマハルジアナム（Ｔｒｉｃｈｏｄｅｒｍａｈａｒｚｉａｎｕｍ）、トリコデルマビリデ（Ｔｒｉｃｈｏｄｅｒｍａｖｉｒｉｄｅ）、トリコデルマビレンス（Ｔｒｉｃｈｏｄｅｒｍａｖｉｒｅｎｓ）、トリコデルマポリスポラム（Ｔｒｉｃｈｏｄｅｒｍａｐｏｌｙｓｐｏｒｕｍ）、トリコデルマハルジアナムリファイ（Ｔｒｉｃｈｏｄｅｒｍａｈａｒｚｉａｎｕｍｒｉｆａｉ）、トリコデルマリグノラン（Ｔｒｉｃｈｏｄｅｒｍａｌｉｇｎｏｒｕｍ ), Tricyclazole, triticonazole, tridemorph, triflumizole, trifluorostrobin, trifolia, trifolia tolylfluand, tolclophos-methyl, tolnifanide, tolprocarb, nabam, natamycin, naftifin, naftifin ）、ヌアリモル（ｎｕａｒｉｍｏｌ）、ノニルフェノールスルホン酸銅（ｃｏｐｐｅｒｎｏｎｙｌｐｈｅｎｏｌｓｕｌｐｈｏｎａｔｅ）、パエニバチルスポリミキサ（Ｐａｅｎｉｂａｃｉｌｌｕｓｐｏｌｙｍｙｘａ）、バークホルデリアセパシア（Ｂａｒｋｈｏｌｄｅｒｉａｃｅｐａｃｉａ）、バチルスアミロリケファシエンス（Ｂａｃｉｌｌｕｓａｍｙｌｏｌｉｑｕｅｆａｃｉｅｎｓ）、バチルスシンプレクス（Ｂａｃｉｌｌｕｓｓｉｍｐｌｅｘ） , Bacillus subtilis, Bacillus pumilus, Bacillus mycoides, Bacillus licheniformis, Bacillus licheniformis, harpin protein (harpin protein) , Varifenalate, pantoea agglomerans, picarbutrazox, bicaxafen, picoxystrobin, picoxystrobim ), Bittertanol, binapacryl, hinokithiol, non-pathogenic erwinia carotovora, non-pathogenic lysobium vitis hymexazol), pyraoxystrobin, pi Lacrostrobin, pyraziflumid, pyrazophos, pyrapropoine, pyrametostrobin, pyrametostrobi, pyriophenone, pyriophenone, pyrisophenone, pyrisophenone, pyrisophos pyriphenox, pyribuchicarb, pyribencarb, pyrimethanil, pyroquilon, vinclozolin, vinclozolin, ferbam, famoxadon, famoxadon Fenaminstrobin, fenarimol, fenoxanil, ferrimzone, fenpiclonil, fenpicoxamide, fenpicoxamide, fenpyrazamin, fenpyrazamine, fenpyrazamine ), Fenpropidin, fenpropimorph, fenhexamide, folpet, phthalide, fusarium oxysporum, bupirimate bupirimate , Blasticidin-S, furametopyl, furalaxyl, furancarboxylacid, fluazinam, fluindapyl, fluindapyl, fluindapyl Piprolin, fluoxythioconazole, fluopiclide, fluopimo Mido (fluopimomide), fluopylam, fluoroimide, fluxapyroxad, fluquinconazole, fluquonazole, fluconazole, fluconazole, fluconazole, fluconazole, fluconazol (Flusylazole), flusulfamide, fluthianil, flutranil, flutriafol, fluphenoxadiazam, fluphenoxydiazam, fluphenoxystrobin Lim (flumetylsulfamide), flumethover, flumorph, flubiopsis gigantea, proquinazid, probenazole, probenazole, probenazole, probenazole, probenazole, probenazole, probenazole, probenazole, probenazole, probenazole, probenazole, probenazole, probenazole (Bronopol), propamocarb-hydrate, propiconazole, probeneb, probenazole, fluoroimide, fluoroimide, fluoroimide, fluoroimide, fluoroimide, bronopol, bronopol, bronopol, bronopol, bronopol , Hexaconazole, benalaxyl, benalaxyl-M, benodanil, benomyl, pefurazoate, penconazole, penconazole, penconazole, penconazole, penconazole Pills (benzovindiflupyr), benchazole (benthiazole), benchavaricarb-isop copper, penthiopyrad, penflufen, boscalid, fosetyl (including salts of aluminum, calcium, sodium, etc.), polyoxin, polycarbamate (polycarbamate) ), Mancopper, mancozeb, mandipropamide, mandestrobin, maneb, microbutanil, mineral oil, mineral oil, mineral oil, mill. Sulfocarb, metam, metalaxyl, metalaxyl-M, metallylpicoxamide, metyllam, methyltetraplat, methyltetraplol, etc. , Metominostrobin, metrafenone, mepanipyrim, mefentrifluconazole, meptyldinocup, meptyldinocap, mepronila, mepronila, mepronil Phosphorous acid and salts, basic copper chloride, silver, copper (II) sulfate, cuprous oxide, cupric hydroxide ( copper hydride, potassium hydrogen carbonate (potassium bicarbonate), sodium hydrogen carbonate (sodium bicarbonate), sulfur (sulfur), oxyquinoline sulfate (oxyquinoline sulfate), copper sulfate (copper sulfate), copper sulfate (copper sulfate) Copper sulphate bisethylenediamine copper complex salt [II] (DBEDC), trife acetate Nyltin (TPTA), triphenyltin chloride (TPTC), triphenyltin hydroxide (TPTH).

Next, known biopesticide that may be mixed or used in combination is illustrated below.

Biopesticide:
アカメガシワクダアザミウマ（Ｈａｐｌｏｔｈｒｉｐｓｂｒｅｖｉｔｕｂｕｓ）、アリガタシマアザミウマ（Ｆｒａｎｋｌｉｎｏｔｈｒｉｐｓｖｅｓｐｉｆｏｒｍｉｓ）、イサエアヒメコバチ（Ｄｉｇｌｙｐｈｕｓｉｓａｅａ）、オンシツツヤコバチ（Ｅｎｃａｒｓｉａｆｏｒｍｏｓａ）、ククメリスカブリダニ（Ａｍｂｌｙｓｅｉｕｓｃｕｃｕｍｅｒｉｓ）、クワコナコバチ（Ｐｓｅｕｄａｐｈｙｃｕｓｍａｌｉｎｕｓ）、ケナガカブリダニ（Ａｍｂｌｙｓｅｉｕｓｗｏｍｅｒｓｌｅｙｉ）、コレマンアブラバチ（Ａｐｈｉｄｉｕｓｃｏｌｅｍａｎｉ）、サバクツヤコバチ（Ｅｒｅｔｍｏｃｅｒｕｓｅｒｅｍｉｃｕｓ）、ショクガタマバエ（Ａｐｈｉｄｏｌｅｔｅｓａｐｈｉｄｉｍｙｚａ）スワルスキーカブリダニ（Ａｍｂｌｙｓｅｉｕｓｓｗｉｒｓｋｉｉ）、タイリクヒメハナカメムシ（Ｏｒｉｕｓｓｔｒｉｇｉｃｏｌｌｉｓ）、チリカブリダニ（Ｐｈｙｔｏｓｅｉｕｌｕｓｐｅｒｓｉｍｉｌｉｓ）、デジェネランスカブリダニ（Ａｍｂｌｙｓｅｉｕｓｄｅｇｅｎｅｒａｎｓ）、トモノカブリダニ（Ｐｈｙｔｏｓｅｉｕｌｕｓｐｅｒｓｉｍｉｌｉｓ）、ナミヒメハナカメムシ（Ｏｒｉｕｓｓａｕｔｅｒｉ）、ハモグリコマユバチ（Ｄａｃｎｕｓａｓｉｂｉｒｉｃａ）、ミヤコカブリダニ（Ａｍｂｌｙｓｅｉｕｓｃａｌｉｆｏｒｎｉｃｕｓ）、ヤマトクサカゲロウ（Ｃｈｒｙｓｏｐｅｒｌａｎｉｐｐｏｎｅｎｓｉｓ）、ルビーアカヤドリKobachi (Anicetus beneficus).

Next, known agricultural materials that may be mixed or used together are illustrated below.

Agricultural materials:
Ethylene, hypochlorite water (limited to those obtained by electrolyzing hydrochloric acid or potassium chloride aqueous solution), sodium bicarbonate, vinegar, humus, humic acid, fluboic acid, seaweed extract, polysaccharides, amino acids, microorganisms Materials, functional ingredients derived from animals and plants, microbial metabolites, microbial activators, soil spreading agents, soil permeability control materials, soil water retention materials, etc., and biostimulants.

Next, the known agricultural fertilizer components that may be mixed or used in combination are illustrated below. Fertilizers include inorganic fertilizers and organic fertilizers.

Agricultural fertilizer component:
Ammonium chloride, ammonium sulfate, ammonium nitrate, ammonium dihydrogen phosphate, urea ammonium nitrate, urea, lime nitrogen, potassium nitrate, lime perphosphate, triple superphosphate, potassium dihydrogen phosphate, potassium chloride, potassium sulfate, potassium carbonate, Potassium silicate, potassium phosphite, oil cake, fish flour, rice bran, bat guano, fermented chicken manure.

The herbicide of the present invention is applied to useful plants, or places where useful plants are to be grown or grown, or to non-agricultural land at the same time or by dividing them into useful plants. It is possible to control the growth of undesired plants or plants that are undesired in terms of land management.

The useful plants referred to in the present invention include field crops or paddy crops, horticultural crops (vegetables, fruit trees), ornamental trees (flowering trees, street trees), shiva, flowers, and foliage plants. It includes, but is not limited to, medicinal plants and timbers, including, but not limited to, the following.

Field crops or paddy crops:
Corn, rice, wheat, durum wheat, barley, lime, rye wheat, spelled wheat, club wheat, embaku, sorghum, cotton, soybean, alfalfa, peanut (light bean), pea (green bean), lye, azuki, sage, ryokuto, uradomame , Benibanaingen, ricebean, moth bean, teparly bean, soramame, pea, chick, lens bean, rupin, kimame, buckwheat, tensai, rapeseed, canola, sunflower, sugar cane, cassaba, nagaimo, oil palm, nanyouaburi, hemp Benibana, Chanoki, Wheat, Tobacco, Camerina, Tef, Guayur, Paragom tree, etc.

Horticultural crops (vegetables):
Vegetables of the family Brassicaceae (egg, tomatoes, peppers, peppers, potatoes, etc.), vegetables of the family Urina (cucumbers, pumpkins, zucchini, watermelons, melons, squash, etc.) , Karasina, broccoli, cauliflower, etc.), Kiku family vegetables (gobo, shungiku, artichoke, lettuce, etc.), lily family vegetables (negi, onion, garlic, asparagus, etc.), seri family vegetables (carrot, parsley, celery, American bowfew) Etc.), Brassicaceae vegetables (Horensou, Beta vulgaris, etc.), Perilla family vegetables (Shiso, Mint, Basil, Lavender, etc.), Strawberries, Sweet potatoes, Yamanoimo, Satoimo, Sesame, etc.

Horticultural crops (fruit trees):
Nuts (apples, pears, Japanese pears, Chugokunashi, Karin, Marumero, etc.), drupes (peaches, plums, nectarins, seaweeds, apricots, apricots, prunes, etc.), citrus fruits (unshu mikan, oranges, lemons, limes, etc.) Grapefruit, etc.), nuts (kuri, walnut, pear, almond, hazelnut, pistachio, cashew nut, macadamia nut, pecan nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, biwa , Banana, coffee, nut palm, coco palm, apricot palm, etc.

Ornamental wood (flowering trees, roadside trees):
Ash, Kabanoki, Hanamizuki, Eucalyptus, Ginkgo, Lilac, Maple, Kashi, Poplar, Cercis chinensis, Fu, Platanus, Keyaki, Thuja, Mominoki, Tsuga, Nezu, Matsu, Tohi, Ichii, Nire, Tochinoki, Coral, Inumaki, Sugi Hinoki, Croton, Masaki, Japanese photinia, etc.

Shiva:
Zoysia japonica (Zoysia japonica, Zoysia tenuifolia, etc.), Bermudagrass (Gyogishiba, etc.), Bentgrass (Arostis capillaris, Agrostis capillaris, etc.), Bluegrass (Nagahagusa, Osuzumenokatabira, etc.), Fescues (Tall fescue, Agrostis capillaris, etc.) Fescues, etc.), ryegrass (Dactylis, Perennial ryegrass, etc.), Zoysia japonica, Agrostis capillaris, etc.

Flowers, foliage plants:
Rose, carnation, kiku, turkey, kasumisou, gerbera, marigold, salvia, petunia, verbena, tulip, aster, lindo, lily, pansy, cyclamen, orchid, tin orchid, lavender, stock, habutton, primula, poinsettia, gradialus, cattleya , Daisy, Verbena, Cyclamen, Begonia, etc.

Medicinal plants:
Chamomiles, licorice, turmeric, ginseng, Coptis chinensis, peony, poppy, etc.

Lumber:
Abies sachalinensis, spruce, pine, hiba, sugi, cypress, eucalyptus, etc.

In addition, the useful plant referred to in the present invention is a 4-hydroxyphenylpyruvate dioxygenase (4-HPPD) inhibitor such as isoxaflutol, an imazetapill, and an acetolactate synthase (ALS) inhibitor such as thifensulfuron-methyl. Agents, 5-enolpyrvirsikimic acid-3-phosphate (EPSP) synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as gluhocinate, acetyl CoA carboxylase (ACCCace) inhibitors such as setoxydim, flumioxadin, epiriphenacyl Protoporphyrinogen oxidase (PPO) inhibitors such as, photochemical II inhibitors such as bromoxinyl, and herbicides such as dicamba and 2,4-D are imparted by classical breeding methods and gene recombination techniques. Also includes plants that have been cultivated.

Examples of "useful plants" that have been endowed with resistance by classical breeding methods include rapeseed, wheat, sunflower, rice, and corn that are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazetapill. It is already sold under the product name.

Similarly, there are soybeans that are resistant to sulfonylurea-based ALS-inhibiting herbicides such as thifensulfuron-methyl by the classical breeding method, and are already sold under the trade name of STS soybean. Similarly, sorghum resistant to sulfonylurea-based acetolactic acid synthase (ALS) -inhibiting herbicides by classical breeding methods is already on the market. Similarly, sugar beets resistant to thiencarbazone-resistant acetolactic synthase (ALS) -inhibiting herbicides by classical breeding methods are already on the market. Similarly, SR corn, kizarohop-resistant wheat, etc. are examples of useful plants to which resistance to acetyl-CoA carboxylase (ACCace) inhibitors such as trionoxime-based and aryloxyphenoxypropionic acid-based herbicides has been imparted by classical breeding methods. .. Useful plants conferred resistance to acetyl-CoA carboxylase (ACCace) inhibitors are the Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. It is described in Acad. Sci. USA) Vol. 87, pp. 7175-7179 (1990) and the like. Mutant acetyl-CoA carboxylase (ACCace) resistant to acetyl-CoA carboxylase (ACCace) inhibitors has been reported in Weed Science, Vol. 53, pp. 728-746 (2005), and such mutant acetyl-CoA carboxylase. A plant resistant to an acetyl-CoA carboxylase inhibitor can be produced by introducing a gene into a plant by gene recombination technique or by introducing a mutation involved in imparting resistance into a crop acetyl-CoA carboxylase (ACCCace). Furthermore, a base substitution mutation-introduced nucleic acid represented by chimera plasti technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318) is introduced into a plant cell to produce a crop (acetyl CoA carboxylase (acetyl CoA carboxylase). By inducing site-specific amino acid substitution mutations in the ACCace) / herbicide target) gene, plants resistant to acetyl CoA carboxylase (ACCace) inhibitors / herbicides can be created.

Examples of useful plants that have been endowed with resistance by gene recombination technology include glyphosate-resistant corn, soybean, cotton, rapeseed, tensai, and alfalfa varieties, Roundup Ready <registered trademark>, Roundup Lady 2. (Roundup Ready 2) <Registered Trademark>, Agrisure-GT (AgrisureGT) <Registered Trademark>, etc. are already on sale. Similarly, there are glufosinate-resistant corn, soybean, cotton, and rapeseed varieties produced by genetic recombination technology, which are already sold under trade names such as LibertyLink (registered trademark). Similarly, bromoxynil-resistant cotton produced by gene recombination technology is already sold under the trade name of BXN. Similarly, soybeans resistant to HPPD inhibitors by genetic recombination technology are trade names of Herbicide-tolerant Soybean line as varieties resistant to mesotrione and glufosinate, and Credenz as varieties resistant to HPPD inhibitors, glyphosate and glufosinate. ) Already sold under product names such as <registered trademark>. Similarly, 2,4-D or ACCase inhibitor-resistant corn, soybean, and cotton produced by genetically modified technology are already sold under trade names such as Enlist (registered trademark). Similarly, soybeans resistant to dicamba by genetically modified technology are already sold under trade names such as Roundup Ready 2 Xtend <registered trademark> as varieties resistant to dicamba and glyphosate. Similarly, a soybean variety that is resistant to HPPD inhibitors such as isoxaflutol and also resistant to nematodes due to HPPD inhibitor resistance by genetic recombination technology has been registered as GMB151 in the United States.

Further plants with modified herbicide resistance are widely known, for example, alfalfa, apple, corn, eucalyptus, flax, grape, corn, rapeseed, pea, potato, rice, millet, which are resistant to glyphosate. , Sunflower, Tobacco, Tomato Millet and Wheat (see, eg, US5188642, US49408835, US5633435, US58044425, US5627061), Herbicide-tolerant beans, cotton, soybeans, pea, potatoes, sunflowers, tomatoes, tobacco, Corn, sorghum and sugar cane (see, eg, WO2008 / 051633, US7105424 and US5670454), soybeans, millets, potatoes, tomatoes and tobacco resistant to gluhosinate (see, eg, US6376754, US5646024, US5561236), 2,4 -D resistant cotton, peppers, apples, tomatoes, sunflowers, tobacco, potatoes, corn, cucumber, wheat, soybeans, sorghum and miscellaneous grains (eg, US6153401, US6100446, WO2005 / 107437, US5608147 and US5674044). See), ALS-inhibiting herbicides (eg, sulfonylurea herbicides, or imidazolinone herbicides), canola, corn, corn, millet, corn, cotton, millet, lettuce, lens bean, melon, awa, oat, For nata, potato, rice, lime, sorghum, soybean, tensai, sunflower, tobacco, tomato and wheat (see, for example, US5013659, WO2006 / 0606634, US4761373, US53047332, US621138, US621314 and US6222100), especially for imidazolinone herbicides. Resistant rice is known and has specific mutations in the acetolactyl synthase gene (eg, S653N, S654K, A122T, S653 (At) N, S654 (At) K, A122 (At) T (eg). , US2003 / 0217381, WO2005 / 020673), HPPD inhibitory herbicides (eg, isoxazole herbicides such as isoxaflutol, triketone herbicides such as sulcotrione, methotrion, and pyrazole herbicides such as pyrazolinete) or Of the degradation products of isoxaflutol Millets, sugar cane, rice, corn, tobacco, soybeans, cotton, rapeseed, sugar beet, wheat and potatoes resistant to diketonitrile (see, eg, WO2004 / 055911, WO1996 / 38567, WO1997 / 049816 and US6791014), and PPO. Wheat, soybean, cotton, tensai, rapeseed, rice, corn, sorghum, sugar cane and sugar beet (eg, US2002 / 0073443, US2008 / 0052798, Pest Management Science, 61, 2005, 277-285) resistant to inhibitory herbicides. See).

Rice "Clearfield <registered trademark> Rice" that is resistant to imidazolinone-based ALS-inhibiting herbicides such as imazetapill and imazamox as plants to which herbicide resistance has been imparted by conventional cultivar improvement technology or genome breeding technology. , Wheat "Clearfield <Registered Trademark> White", Sunflower "Clearfield <Registered Trademark> Sunflower", Lens Mame "Clearfield <Registered Trademark> lentils" and Canola "Clearfield <Registered Trademark> canola" Soybean "STS soybean" resistant to ALS-inhibiting herbicides, corn "SR cone" resistant to acetyl CoA carboxylase inhibitors such as trionoxime herbicides, aryloxyphenoxypropionic acid herbicides, etc. Also known as "corn"), sunflower "ExpressSun <registered trademark>" resistant to sulfonylurea herbicides such as trivenuron, rice "Provisia <registered trademark" resistant to acetyl CoA carboxylase inhibitors such as kizarohop. > Rice ”, canola“ Triazine Solarant Canola ”which is resistant to photochemical II inhibitors, and sorghum“ Igrowth <registered trademark> ”which is resistant to imidazolinone herbicides.

A sulfonylurea herbicide-resistant canola "SU Canola" (<registered trademark>) using rapid cultivar development technology (Rapid Trait Development System, RTDS <registered trademark>) as a plant to which herbicide resistance has been imparted by genome editing technology. RTDS <registered trademark> corresponds to the introduction of an oligonucleotide-oriented mutation in a genome editing technique, and is used in a plant via a Gene Repair Orivar cultivar (GRON), that is, a chimeric oligonucleotide of DNA and RNA. It is a technique that can introduce mutations without cutting the DNA. As another example, herbicide resistance and phytic acid content were reduced by deleting the endogenous gene IPK1 using a zinc finger nuclease. Examples include corn (see, eg, Nature 459, 437-441, 2009) and rice that has been herbicide-tolerated using crisper casnin (see, eg, Rice, 7, 5, 2014).

As a plant to which herbicide resistance has been imparted by the new breeding technique, for example, soybean having the properties of the GM rootstock imparted to the scion by using the breeding technique using grafting can be mentioned. Specific examples thereof include soybeans (see Weed Technology 2013, 27, 412) in which non-transgenic soybean scion is imparted with glyphosate resistance using Roundup Ready <registered trademark> soybean having glyphosate resistance as a rootstock. ..

The above-mentioned "useful plant" includes, for example, a plant capable of synthesizing a selective toxin known in the genus Bacillus by using a gene recombination technique.

Examples of the insecticidal toxin expressed in such a recombinant plant include insecticidal proteins derived from Bacillus cereus and Bacillus popillia; Cry1Ab and Cry1Ab derived from Bacillus turingiensis. , Cry1F, Cry1Fa2, Cry14Ab-1, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C and other δ-endotoxins, VIP1, VIP2, VIP3 or VIP3A and other insecticidal proteins; nematode-derived insecticidal proteins; scorpion toxins, spider toxins, bees. Toxins produced by animals such as toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectin; aglutinin; trypsin inhibitors, serine protease inhibitors, patatin, cystatin, protease inhibitors such as papain inhibitors; lysine, Ribosome-inactivating proteins (RIPs) such as corn-RIP, abrin, saporin, briodin; steroid-metabolizing enzymes such as 3-hydroxysteroid oxidase, ecdisteroid-UDP-glucosyltransferase, cholesterol oxidase; ecdison inhibitors; HMG-CoA Examples thereof include reductase; ion channel inhibitors such as sodium channel inhibitors and calcium channel inhibitors; immature hormone esterases; diuretic hormone receptors; stylben synthase; bibenzyl synthase; kitinase; glucanase and the like.

Further, as toxins expressed in such transgenic plants, δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry14Ab-1, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34A, Cry34Ab, or Cry35Ab, VIP1 , VIP2, VIP3 or VIP3A and other insecticidal protein hybrid toxins, partially defective toxins, modified toxins. Hybrid toxins are created using recombinant techniques by a new combination of different domains of these proteins. As a toxin lacking a part, Cry1Ab lacking a part of the amino acid sequence is known. As the modified toxin, one or more amino acids of the natural toxin have been replaced.

Examples of these toxins and recombinant plants capable of synthesizing these toxins include, for example, EP-A-0374753, WO93 / 07278, WO95 / 34656, EP-A-0427529, EP-A-451878, WO03 / 052073 and the like. It is described in the patent document of. The toxins contained in these recombinant plants confer resistance to Coleoptera, Diptera, and Lepidopteran pests, in particular.

Also, transgenic plants containing one or more insecticidal pest resistance genes and expressing one or more toxins are already known, and some are commercially available. Examples of these recombinant plants include YieldGard <registered trademark> (corn varieties expressing Cry1Ab toxin), YieldGuard Rootworm <registered trademark> (corn varieties expressing Cry3Bb1 toxin), and so on. YieldGard Plus <registered trademark> (corn variety expressing Cry1Ab and Cry3Bb1 toxins), Herculex I <registered trademark> (phosphino for conferring resistance to Cry1Fa2 toxins and gluhosinate) Tricin N-acetyltransferase (PAT) -expressing corn varieties), NuCOTN33B <registered trademark> (Cry1Ac toxin-expressing cotton varieties), Bollgard I <registered trademark> (Cry1Ac toxin-expressing cotton varieties), Bollgard II <registered trademark> (Cry1Ac and Cry2Ab toxin-expressing cotton varieties), VIPCOT <registered trademark> (VIP toxin-expressing cotton varieties), NewLeaf <registered trademark> (Cry3A toxin) Expressed potato varieties), Nature Guard GT Advantage (NatureGard <registered trademark> Agrisure <registered trademark> GT Advantage (GA21 glyphosate resistant trait), Agrisure CB Advantage (Registered Trademark) CB (CB) trait), protecta <registered trademark> and the like.

The above-mentioned useful plants include those imparted with the ability to produce an antipathogenic substance having a selective action by using a gene recombination technique.

Examples of anti-pathogenic substances include PR proteins (described in PRPs, EP-A-03922225); sodium channel inhibitors, calcium channel inhibitors (KP1, KP4, KP6 toxins produced by viruses, etc.). Ion channel inhibitors such as (stilben synthase; bibenzyl synthase; chitinase; glucanase; peptide antibiotics, antibiotics with heterocycles, protein factors involved in plant disease resistance (called plant disease resistance genes) Examples thereof include substances produced by microorganisms such as (described in WO03 / 000906). Such anti-pathogenic substances and the genetically modified plants that produce them are described in EP-A-0392225, WO95 / 33818, EP-A-0353191 and the like.

The above-mentioned useful plants include crops to which useful traits such as oil component modification and amino acid content enhancing traits have been imparted by using gene recombination technology. Examples thereof include VISTIVE <registered trademark> (low linolene soybean with reduced linolene content), high-lysine (high foil) corn (corn with increased lysine or oil content), and the like.

The above-mentioned useful plants include crops that have been imparted with useful traits such as drought tolerance by using genetic recombination technology to maintain or increase the yield. Examples thereof include DrughhtGard <registered trademark> (corn imparted with drying resistance) and the like.

The herbicide of the present invention also exhibits a control effect on the pests and the like exemplified above, which have acquired resistance to existing herbicides. In addition, the herbicide of the present invention can also be used for plants that have acquired characteristics such as pest resistance, disease resistance, and herbicide resistance by genetic recombination, artificial mating, and the like.

The "plant to which resistance has been imparted by a breeding method or gene recombination technique" of the present invention is not only resistance conferred by classical breeding and resistance conferring by gene recombination technology, but also molecular biology in conventional mating techniques. Includes plants that have been endowed with resistance by a new breeding technology (New Plant Breeding Technologies, NBTs) that combines these methods. New breeding techniques (NBTs) are the book "Let's understand new plant breeding techniques" (International Literature, Ryo Osawa, Hiroshi Egami), review article "Genome Editing Tools in Plants" (Genes 2017, 8, 399, Tapan Kumar Mohanta). , Tufail Bashir, Abere Hashem, Elsaid Fathi Abd_Allah and Hanhong Bay) and the like. Examples of the above-mentioned new breeding techniques include genome breeding techniques and genome editing techniques. Genome breeding technology is a technology for improving the efficiency of breeding using genomic information, and includes DNA marker (also called genomic marker or gene marker) breeding technology and genomic selection. For example, DNA marker breeding is a method of selecting a progeny having a desired useful trait gene from a large number of mating progeny using a DNA marker which is a DNA sequence that serves as a marker for the position of a specific useful trait gene on the genome. be. By analyzing the mating progeny using DNA markers when they are young plants, it has the characteristic that the time required for breeding can be effectively shortened.

In addition, genomic selection is a method of creating a prediction formula from the phenotype and genomic information obtained in advance, and predicting the characteristics from the prediction formula and genomic information without evaluating the phenotype, which contributes to the efficiency of breeding. It is a possible technology. New breeding technology (new breeding techniques) is a general term for breeding technology that combines molecular biological techniques. For example, sysgenesis / intragenesis, oligonucleotide-oriented mutagenesis, RNA-dependent DNA methylation, genome editing, grafting to GM rootstock or scion, reverse breeding, agroinfiltration, seed production technology (Seed Production). There are technologies such as Technology (SPT). Genome editing technology is a technology for converting genetic information in a sequence-specific manner, and can delete a base sequence, replace an amino acid sequence, introduce a foreign gene, or the like. As the tools, for example, zinc finger nucleases (Zinc-Finer Nucleases, ZFN, ZFNs) capable of sequence-specific cleavage, TALEN, CRISPR / Cas9, and CRISPR / CRISPR / Cpf1) and Meganuclease. In addition, there are sequence-specific genome modification techniques such as CAS9 nickase and Target-AID prepared by modifying the above-mentioned tools.

Furthermore, regarding useful traits such as the above-mentioned classical herbicide traits or herbicide resistance genes, insecticidal pest resistance genes, antipathogenic substance production genes, oil component modification, amino acid content enhancing traits, and drought resistance traits. , Stack varieties that combine multiple of these are also included.

Non-agricultural land as a usage scene of the herbicide of the present invention and the pesticide composition containing the herbicide of the present invention includes, for example, embankment slope, riverbed, road shoulder and slope, railroad floor, park green land, ground. , Parking lots, airports, industrial land such as factories and storage facilities, fallow land, or non-agricultural land that needs to control the growth of weeds such as fallow in the city, or orchards, pastures, lawns. , Forestry land, rivers, waterways, canals, reservoirs, etc.

As described above, the herbicide of the present invention and the pesticide composition containing the herbicide of the present invention have a herbicidal effect on various weeds. The weeds are illustrated below, but are not limited to these examples.

Urticaceae: Urticaceae:
Small Nettle (Urtica urens).

Polygonaceae: Polygonaceae:
ソバカズラ（Ｐｏｌｙｇｏｎｕｍｃｏｎｖｏｌｖｕｌｕｓ）、サナエタデ（Ｐｏｌｙｇｏｎｕｍｌａｐａｔｈｉｆｏｌｉｕｍ）、アメリカサナエタデ（Ｐｏｌｙｇｏｎｕｍｐｅｎｓｙｌｖａｎｉｃｕｍ）、ハルタデ（Ｐｏｌｙｇｏｎｕｍｐｅｒｓｉｃａｒｉａ）、イヌタデ（Ｐｏｌｙｇｏｎｕｍｌｏｎｇｉｓｅｔｕｍ）、ミチヤナギ（Ｐｏｌｙｇｏｎｕｍａｖｉｃｕｌａｒｅ）、ハイミチヤナギ（Ｐｏｌｙｇｏｎｕｍａｒｅｎａｓｔｒｕｍ）、イタドリ（Ｐｏｌｙｇｏｎｕｍｃｕｓｐｉｄａｔｕｍ）、 Prostrate knotweed (Rumex japonicus), Prostrate knotweed (Rumex crispus), Prostrate knotweed (Rumex obtusifolius), Suiva (Rumex acetosa), Knotweed (Rumex acetosella), Knotweed.

Portulacaceae:
Portulaca oleracea.

Caryophyllaceae:
Chickweed (Stellaria media), Giant Chickweed (Stellaria aquatica), Mouse-ears (Cerastium holosteoides), Sticky mouse-ear (Cerastium glomeratum), Otsumexa (Spergalina seri)

Molluginaceae:
Car Bazakurosou (Mollugo verticillata).

Amaranthaceae:
アオゲイトウ（Ａｍａｒａｎｔｈｕｓｒｅｔｒｏｆｌｅｘｕｓ）、ホナガイヌビユ（Ａｍａｒａｎｔｈｕｓｖｉｒｉｄｉｓ）、イヌビユ（Ａｍａｒａｎｔｈｕｓｌｉｖｉｄｕｓ）、ハリビユ（Ａｍａｒａｎｔｈｕｓｓｐｉｎｏｓｕｓ）、ホナガアオゲイトウ（Ａｍａｒａｎｔｈｕｓｈｙｂｒｉｄｕｓ）、オオホナガアオゲイトウ（Ａｍａｒａｎｔｈｕｓｐａｌｍｅｒｉ）、ホソアオゲイトウ（Ａｍａｒａｎｔｈｕｓｐａｔｕｌｕｓ）、ウォーターヘンプ（Ａｍａｒａｎｔｈｕｓｔｕｂｅｒｃｕｌａｔｕｓ＝Ａｍａｒａｎｔｈｕｓｒｕｄｉｓ＝Ａｍａｒａｎｔｈｕｓｔａｍａｒｉｓｃｉｎｕｓ）、アメリカビユ（Ａｍａｒａｎｔｈｕｓｂｌｉｔｏｉｄｅｓ）、ハイビユ（Ａｍａｒａｎｔｈｕｓｄｅｆｌｅｘｕｓ）、アマランサスクイテンシス（Ａｍａｒａｎｔｈｕｓｑｕｉｔｅｎｓｉｓ）、ハリビユ（Ａｍａｒａｎｓｈｕｓｓｐｉｎｏｓｕｓ）、ナガエツルノゲイトウ（Ａｌｔｅｒｎａｎｔｈｅｒａｐｈｉｌｏｘｅｒｏｉｄｅｓ）、ツルゲイトウ（Ａｌｔｅｒｎａｎｔｈｅｒａｓｅｓｓｉｌｉｓ）、サングイナリア（Ａｌｔｅｒｎａｎｔｈｅｒａｔｅｎｅｌｌａ）、イガホビユ（Ａｍａｒａｎｔｈｕｓｐｏｗｅｌｉｉ）、ホソバイヌビユ（Ａｍａｒａｎｔｈｕｓｒｕｄｉｓ）、ヒメシロビユ（Ａｍａｒａｎｔｈｕｓａｌｂｕｓ）、アオビユ（Ａｍａｒａｎｔｈｕｓｖｉｒｉｄｉｓ）、イヌビユ（Ａｍａｒａｎｔｈｕｓｌｉｖｉｄｕｓ）、ホソアオゲイトウ（Ａｍａｒａｎｔｈｕｓｐａｔｕｌｕｓ）、シロザ（Ｃｈｅｎｏｐｏｄｉｕｍａｌｂｕｍ） , Kearitasou (Chenopodium ambrosioides), Houkigi (Kochia scoparia), Noharahijiki (Salola kali), Atriplex spp.

Papaveraceae:
Poppy (Papaver rhoeas), Papaver dubium (Papaver dubium), Prickly poppy (Argemone Mexicana).

Brassicaceae:
Yellowcresses (Raphanus raphanistrum), Radish (Raphanus sativus), Yellowcresses (Sinapis arvensis), Yellowcresses (Capsella bursa-pastoris), Yellowcresses (Brassica bassa) Ｄｅｓｃｕｒａｉｎｉａｐｉｎｎａｔａ）、スカシタゴボウ（Ｒｏｒｉｐｐａｉｓｌａｎｄｉｃａ）、キレハイヌガラシ（Ｒｏｒｉｐｐａｓｙｌｖｅｓｔｒｉｓ）、グンバイナズナ（Ｔｈｌａｓｐｉａｒｖｅｎｓｅ）、ミヤガラシ（Ｍｙａｇｒｕｍｒｕｇｏｓｕｍ）、マメグンバイナズナ（Ｌｅｐｉｄｉｕｍｖｉｒｇｉｎｉｃｕｍ）、カラクサナズナ（Ｃｏｒｏｎｏｐｕｓｄｉｄｙｍｕｓ）、クジラグサ（Ｄｅｓｃｕｒａｒｉｎｉａｓｏｐｈｉａ） , Yellowcresses (Rorippa indica), Yellowcresses (Simnrim office), Yellowcresses (Cardamine flexuosa), Yellowcresses (Nastrutum office), Yellowcresses (Drabane).

Capparaceae:
Creome affinis.

Legumes (Fabaceae):
クサネム（Ａｅｓｃｈｙｎｏｍｅｎｅｉｎｄｉｃａ）、ジグザグジョイントベッチ（Ａｅｓｃｈｙｎｏｍｅｎｅｒｕｄｉｓ）、エシノメネデンティクラータ（Ａｅｓｃｈｙｎｏｍｅｎｅｄｅｎｔｉｃｕｌａｔａ）、エシノメネルディス（Ａｅｓｃｈｙｎｏｍｅｎｅｒｕｄｉｓ）、アメリカツノクサネム（Ｓｅｓｂａｎｉａｅｘａｌｔａｔａ）、エビスグサ（Ｃａｓｓｉａｏｂｔｕｓｉｆｏｌｉａ）、ハブソウ（Ｃａｓｓｉａｏｃｃｉｄｅｎｔａｌｉｓ）、ジュズハギ（Ｄｅｓｍｏｄｉｕｍｔｏｒｔｕｏｓｕｍ）、ノハラハギ（Ｄｅｓｍｏｄｉｕｍａｄｓｃｅｎｄｅｎｓ）、イリノイヌスビトハギ（Ｄｅｓｍｏｄｉｕｍｉｌｌｉｎｏｅｎｓｅ）、シロツメクサ（Ｔｒｉｆｏｌｉｕｍｒｅｐｅｎｓ）、クズ（Ｐｕｅｒａｒｉａｌｏｂａｔａ）、カラスノエンドウ（Ｖｉｃｉａａｎｇｕｓｔｉｆｏｌｉａ）、タヌキコマツナギ（Ｉｎｄｉｇｏｆｅｒａｈｉｒｓｕｔａ）、インディゴフェラAeschynomene (Indigofera turuxillensis), Sassage (Vigna sinensis), Crotalaria incana, Okarasuno pea (Vicia siva), Common Vetch (Vetch) , Umago palm (Medicago polymorpha).

Oxalidaceae:
Oxalis corniculata, Oxalis strica, Oxalis oxyptera, Oxalis debilis.

Geraniaceae:
American geranium (Geranium carolinense), Dutch crane's-football (Erodium caturium), Dove's Foot Crane's-bill (Geranium molle), Hedgerow Crabe's-bill (Geranium pyrena).

Euphorbiaceae: Euphorbiaceae:
トウダイグサ（Ｅｕｐｈｏｒｂｉａｈｅｌｉｏｓｃｏｐｉａ）、オオニシキソウ（Ｅｕｐｈｏｒｂｉａｍａｃｕｌａｔａ）、コニシキソウ（Ｅｕｐｈｏｒｂｉａｈｕｍｉｓｔｒａｔａ）、ハギクソウ（Ｅｕｐｈｏｒｂｉａｅｓｕｌａ）、ショウジョウソウ（Ｅｕｐｈｏｒｂｉａｈｅｔｅｒｏｐｈｙｌｌａ）、ヒソップリーフサンドマット（Ｅｕｐｈｏｒｂｉａｂｒａｓｉｌｉｅｎｓｉｓ）、エノキグサ（Ａｃａｌｙｐｈａａｕｓｔｒａｌｉｓ）、トロピッククロトン（Ｃｒｏｔｏｎｇｌａｎｄｕｌｏｓｕｓ）、ロブドクロトン（Ｃｒｏｔｏｎｌｏｂａｔｕｓ）、ブラジルコミカンソウ（Ｐｈｙｌｌａｎｔｈｕｓｃｏｒｃｏｖａｄｅｎｓｉｓ）、トウゴマ（Ｒｉｃｉｎｕｓｃｏｍｍｕｎｉｓ）、アストレアロバタ（Ａｓｔｒａｅａｌｏｂａｔａ）、シマニシキソウ（Ｃｈａｍａｅｓｙｃｅｈｉｒｔａ）、ショウジョウソウモドキ（Ｃｈａｍａｅｓｙｃｅｈｙｓｓｏｐｉｆｏｌｉａ） ..

Malvaceae:
Velvetleaf, Sida cordifolia, Sida cordifolia, Sida spinosa, Sida sida sida sida sida sida sida sida sida sida sida sida sida Sida cordifolia (Hibiscus trionum), Nishikiaoi (Anoda cristata), Enokiaoi (Malvastrum color anddelianum), Chinese bar (Triumfetta rhomboidea).

Evening Primrose Weeds:
Ludwigia epilivioides, Ludwigia octovalvis, Ludwigia decurre, evening primrose, evening primrose, evening primrose, evening primrose, evening primrose, evening primrose, evening primrose, evening primrose, evening primrose, evening primrose.

Sterculiaceae:
Kobanbanoki (Waltheria indica)
Violaceae: Violet arvensis, wild pansy (Viola tricolor).

Cucurbitaceae:
Bur-cucumber (Sicyos angulatus), wild cucumber (Echinocystis lobata), bitter melon (Momodica charantia).

Lythraceae:
Lythrum anceps (Ammannaia multiflora), Nangoku lythraceae (Ammannaia auriculata), Lythrum anceps (Ammannaia coccinea), Purple Loosestrife (Lythrum salicaria), Rotala indica.

Elatinaceae: Elatinaceae:
Elatine triandra, California water wort (Elatine triandra).

Umbelliferae weeds (Apiaceae):
Auction (Oenanthe javanica), wild carrot (Daucus carrota), poison hemlock (Conumm aculatum), pineapple (Cyclospermum leptophyllum).

Araliaceae:
Hydrocotyle sibthorpioides, Brazilian water pennyworts (Hydrocotyle ranunculoides).

Ceratophyllaceae: Ceratophyllaceae:
Coontail (Ceratophyllum demersum).

Cabombaceae weeds:
Cabomba caroliniana.

Haloragis aceae:
Parrot's feather (Myriophyllum aquaticum), watermilfoils (Myriophyllum verticillatum), Myriophyllum matogrossense, watermilfoils (Myriophyllum lyllum), watermilfoils, etc.

Sapindaceae:
Balloon vine (Cardiospermum halicacabum).

Primula family weeds (Primulaceae):
Pimpernels (Angallis arvensis).

Asclepiaceae:
Milkweed (Asclepias syriaca), Honey Vine Milkweed (Amplamus albidus).

Rubiaceae:
Cleavers (Galium spurium), Galium (Galium spurium var. Echinospermon), Hiroha Futabumgra (Spermacoce latifolia), Hexasepalum vulgaris (Diodella teres), Brazilian Hashikagu

Convolvulaceae Weeds (Convolvulaceae):
アサガオ（Ｉｐｏｍｏｅａｎｉｌ）、アメリカアサガオ（Ｉｐｏｍｏｅａｈｅｄｅｒａｃｅａ）、マルバアサガオ（Ｉｐｏｍｏｅａｐｕｒｐｕｒｅａ）、マルバアメリカアサガオ（Ｉｐｏｍｏｅａｈｅｄｅｒａｃｅａｖａｒ．ｉｎｔｅｇｒｉｕｓｃｕｌａ）、マメアサガオ（Ｉｐｏｍｏｅａｌａｃｕｎｏｓａ）、ホシアサガオ（Ｉｐｏｍｏｅａｔｒｉｌｏｂａ）、ノアサガオ（Ｉｐｏｏｅａａｃｕｍｉｎａｔａ）、ツタノハルコウ（Ｉｐｏｍｏｅａｈｅｄｅｒｉｆｏｌｉａ）、マルバルコウ（Ｉｐｏｍｏｅａｃｏｃｃｉｎｅａ）、ルコウソウ（Ｉｐｏｍｏｅａｑｕａｍｏｃｌｉｔ）、イポモエアグランディフォリア（Ｉｐｏｍｏｅａｇｒａｎｄｉｆｏｌｉａ）、イポモエアアリストロチアフォリア（Ｉｐｏｍｏｅａａｒｉｓｔｏｌｏｃｈｉａｆｏｌｉａ）、モミジバヒルガオ（Ｉｐｏｍｏｅａｃａｉｒｉｃａ）、セイヨウヒルガオ（Ｃｏｎｖｏｌｖｕｌｕｓａｒｖｅｎｓｉｓ） , Kohilgao (Calystegia hederacea), Hilgao (Calystegia japonica), Tsutanoha hirugao (Merremia hedeacea), Hairywood rose (Merremia aegyptia), Roadside wood rose (Merremia aegyptia)

Boraginaceae:
Forget-me-nots (Myosotis arvensis), Myosotis arvensis, Inumurasaki (Lithospermum office), Shazenmurasaki (Echium plantagineum), Nanbanrurisou (Helio).

Labiatae (Lamiaceae):
ヒメオドリコソウ（Ｌａｍｉｕｍｐｕｒｐｕｒｅｕｍ）、ホトケノザ（Ｌａｍｉｕｍａｍｐｌｅｘｉｃａｕｌｅ）、タマザキメハジキ（Ｌｅｏｎｏｔｉｓｎｅｐｅｔａｅｆｏｌｉａ）、ニオイニガクサ（Ｈｙｐｔｉｓｓｕａｖｅｏｌｅｎｓ）、ヒプティスロファンタ（Ｈｙｐｔｉｓｌｏｐｈａｎｔａ）、メハジキ（Ｌｅｏｎｕｒｕｓｓｉｂｉｒｉｃｕｓ）、ヤブチョロギ（Ｓｔａｃｈｙｓａｒｖｅｎｓｉｓ）、ヤクモソウ（Ｌｅｏｎｕｒｕｓｓｉｂｉｒｉｃｕｓ） , Marispianthes chamaedris.

Solanaceae:
Nightshade (Datra stramonium), nightshade (Solanum nigrum), nightshade (Solanum americanum), nightshade (Solanum ptychanthum), nightshade (Solanum ptychanthum), nightshade (Solanum ptychanthum), nightshade (Solanum ptychanthum), nightshade (Solanum ptychanthum) Wild tomato (Solanum sisym briifolia), Warnasubi (Solanum carolinense), Sennarihozuki (Physalis angulata), Smooth grand cherry (Physalis subglabrata), Osennari (Nicandra).

Linderniaceae:
Lindernia procumbens, American Lindernia procumbens, Lindernia procumbens.

Plantainaceae:
オオバコ（Ｐｌａｎｔａｇｏａｓｉａｔｉｃａ）、ヘラオオバコ（Ｐｌａｎｔａｇｏｌａｎｃｅｏｌａｔａ）、セイヨウオオバコ（Ｐｌａｎｔａｇｏｍａｊｏｒ）、ミズハコベ（Ｃａｌｌｉｔｒｉｃｈｅｐａｌｕｓｔｒｉｓ）、キクモ（Ｌｉｍｎｏｐｈｉｌａｓｅｓｓｉｌｉｆｌｏｒａ）、アブノメ（Ｄｏｐａｔｒｉｕｍｊｕｎｃｅｕｍ）、オオアブノメ（Ｇｒａｔｉｏｌａｊａｐｏｎｉｃａ）、ウキアゼナ（Ｂａｃｏｐａｒｏｔｕｎｄｉｆｏｌｉａ）、フラサバソウ(Veronica hederaefolia), Persian speedwell (Veronica persica), Corn speedwell (Veronica arvensis), Water hyssop (Veronica anagallis-aquatica), Plantagotomenta.

Asteraceae Weeds:
オナモミ（Ｘａｎｔｈｉｕｍｐｅｎｓｙｌｖａｎｉｃｕｍ）、オオオナモミ（Ｘａｎｔｈｉｕｍｏｃｃｉｄｅｎｔａｌｅ）、イガオナモミ（Ｘａｎｔｈｉｕｍｉｔａｌｉｃｕｍ）、ヒマワリ（Ｈｅｌｉａｎｔｈｕｓａｎｎｕｕｓ）、カミツレ（Ｍａｔｒｉｃａｒｉａｃｈａｍｏｍｉｌｌａ）、イヌカミツレ（Ｍａｔｒｉｃａｒｉａｐｅｒｆｏｒａｔａ）、コーンマリーゴールド（Ｃｈｒｙｓａｎｔｈｅｍｕｍｓｅｇｅｔｕｍ）、オロシャギク（Ｍａｔｒｉｃａｒｉａｍａｔｒｉｃａｒｉｏｉｄｅｓ）、ヨモギ（Ａｒｔｅｍｉｓｉａｐｒｉｎｃｅｐｓ）、オウシュウヨモギ（Ａｒｔｅｍｉｓｉａｖｕｌｇａｒｉｓ）、チャイニーズマグウォート（Ａｒｔｅｍｉｓｉａｖｅｒｌｏｔｏｒｕｍ）、セイタカアワダチソウ（Ｓｏｌｉｄａｇｏａｌｔｉｓｓｉｍａ）、セイヨウタンポポ（Ｔａｒａｘａｃｕｍｏｆｆｉｃｉｎａｌｅ）、ハキダメギク（Ｇａｌｉｎｓｏｇａｃｉｌｉａｔａ）、コゴメギク（Ｇａｌｉｎｓｏｇａｐａｒｖｉｆｌｏｒａ）、ノボロギク（Ｓｅｎｅｃｉｏｖｕｌｇａｒｉｓ）、セネシオブラジリエンシス（Ｓｅｎｅｃｉｏｂｒａｓｉｌｉｅｎｓｉｓ）、セネシオグリセバチ（Ｓｅｎｅｃｉｏｇｒｉｓｅｂａｃｈｉｉ）、アレチノギク（Ｃｏｎｙｚａｂｏｎａｒｉｅｎｓｉｓ）、オオアレチノギク（Ｃｏｎｙｚａｓｕｍａｔｒｅｎｓｉｓ）、ヒメムカシヨモギ（Ｃｏｎｙｚａｃａｎａｄｅｎｓｉｓ）、ブタクサ（Ａｍｂｒｏｓｉａａｒｔｅｍｉｓｉｉｆｏｌｉａ）、オオブタクサ（Ａｍｂｒｏｓｉａｔｒｉｆｉｄａ）、 Taukogi (Bidens tripartita), Kosendangusa (Bidens pilosa), American Sendangusa (Bidens frontosa), Bidens subaternans (Bidens subaternans), Cockleburs (Cirsia) Mask Chistle (Carduus nutans), Togechisha (Lactuca seriola), Nogeshi (Sonchus oleraceus), Oninogeshi (Sonchus asper), Beach creeping oxeye (Wedeliaglauca), Perforated blackfoot (Mel) ｐｏｄｉｕｍｐｅｒｆｏｌｉａｔｕｍ）、ウスベニニガナ（Ｅｍｉｌｉａｓｏｎｃｈｉｆｏｌｉａ）、ナンカイウスベニニガナ（Ｅｍｉｌｉａｆｏｓｂｅｒｇｉｉ）、シオザキソウ（Ｔａｇｅｔｅｓｍｉｎｕｔａ）、パラクレス（Ｂｌａｉｎｖｉｌｌｅａｌａｔｉｆｏｌｉａ）、ブラインヴィレアディコトマ（Ｂｌａｉｎｖｉｌｌｅａｄｉｃｈｏｔｏｍａ）、コトブキギク（Ｔｒｉｄａｘｐｒｏｃｕｍｂｅｎｓ）、イェルバポロサ（Ｐｏｒｏｐｈｙｌｌｕｍｒｕｄｅｒａｌｅ ), Paraguay star bar (Acanthospermum australe), Bristolly star bar (Acanthospermum hispidum), Fusengazura (Caldiosperm um halicacabum), False daisy (Ageratum corpora), False daisy (Ageratum coneflower) Ｅｒｅｃｈｔｉｔｅｓｈｉｅｒａｃｉｆｏｌｉａ）、アメリカンエバーラスティング（Ｇａｍｏｃｈａｅｔａｓｐｉｃａｔａ）、ウラジロチチコグサ（Ｇｎａｐｈａｌｉｕｍｓｐｉｃａｔｕｍ）、ジャゲリアヒトラ（Ｊａｅｇｅｒｉａｈｉｒｔａ）、ゴマギク（Ｐａｒｔｈｅｎｉｕｍｈｙｓｔｅｒｏｐｈｏｒｕｓ）、メナモミ（Ｓｉｅｇｅｓｂｅｃｋｉａｏｒｉｅｎｔａｌｉｓ）、メリケントキンソウ（Ｓｏｌｉｖａｓｅｓｓｉｌｉｓ）、タカサブロウ（Ｅｃｌｉｐｔａｐｒｏｓｔｒａｔａ）、トキンソウ（Ｃｅｎｔｉｐｅｄａｍｉｎｉｍａ）、カミツレモドキ（Ａｎｔｈｅｍｉｓｃｏｔｕｌａ）、エゾノキツネアザミ（Ｃｉｒｓｉｕｍｓｅｔｏｓｕｍ）、ヤグルマギク（Ｃｅｎｔｕｒｅａｃｙａｎｕｓ）、オオキンケイギク（Ｃｏｒｅｏｐｓｉｓｌａｎｃｅｏｌａｔａ）、アラゲハンゴンソウ（Ｒｕｄｂｅｃｋｉａｈｉｒｔａ）、オオハンゴンソウ（Ｒｕｄｂｅｃｋｉａｌａｃｉｎｉａｔａ）、ヤエザキCutleaf coneflower (Rubeckia laciniata var. Hortensis Bailey, Bidens subarutemans, Gymnocoronis spiranthoides, Hypochaeris chilensis, pull care sagittaris.

Water-plantain weeds (Alismataceae):
ウリカワ（Ｓａｇｉｔｔａｒｉａｐｙｇｍａｅａ）、オモダカ（Ｓａｇｉｔｔａｒｉａｔｒｉｆｏｌｉａ）、セイヨウオモダカ（Ｓａｇｉｔｔａｒｉａｓａｇｉｔｔｉｆｏｌｉａ）、タイリンオモダカ（Ｓａｇｉｔｔａｒｉａｍｏｎｔｅｖｉｄｅｎｓｉｓ）、アギナシ（Ｓａｇｉｔｔａｒｉａａｇｉｎａｓｈｉ）、ヘラオモダカ（Ａｌｉｓｍａｃａｎａｌｉｃｕｌａｔｕｍ）、サジオモダカ（Ａｌｉｓｍａｐｌａｎｔａｇｏ－ａｑｕａｔｉｃａ）。

Limnocharitaceae: Limnocharitaceae:
Limnocharis flava.

Hydrocharitaceae: Hydrocharitaceae:
Frogbit (Limnobium spongia), waterthyme (Hydrilla verticillata), common water nymph (Najas gudalapensis), Egeria densa.

Araceae:
Pistia stratiotes.

Duckweed Weeds (Lemnaceae):
Lemna aoukiusa, Spirodela polyrhiza, Wolffia globosa.

Pondweed weeds (Potamogetonaceae):
Potamogeton discinctus, Pondweeds (Potamogetoncrispus, Potamogeton illinoensis, Stickenia pectinata, etc.).

Liliaceae:
Wild onion (Allium canadense), wild garlic (Allium vineale), nobile (Allium macrostemon).

Pontederiaceae weeds:
Water hyacinth (Eichornia crascipes), American konagi (Heteranthera limosa), Monochoria korsakowii, Konagi (Monochoria vaginalis), Heterandera reniformis.

Commelinaceae: Commelinaceae:
Dayflower (Commelina communis), Commelina benghalensis, Electdayflower (Commelina erecta), Murdannia keisak, Doveweed (Murdannia).

Poaceae: Poaceae:
Inubie (Echinochloa crus-galli), Tainubier (Echinochloa oryzicola), Himeta barnyardgrass (Echinochloa crus-galli var formosensis), Late water glass (Echinochloa oryzo) (Setaria viridis), Aquino enacologsa (Setaria faveri), Kinenokoro (Setaria grauca), American enocologsa (Setaria geniculata), Mexican barnyardgrass (Digitaria guiliaris) Ｄｉｇｉｔａｒｉａｉｎｓｕｌａｒｉｓ）、オヒシバ（Ｅｌｅｕｓｉｎｅｉｎｄｉｃａ）、スズメノカタビラ（Ｐｏａａｎｎｕａ）、オオスズメノカタビラ（Ｐｏａｔｒｉｖｉａｌｉｓ）、ナガハグサ（Ｐｏａｐｒａｔｅｎｓｉｓ）、スズメノテッポウ（Ａｌｏｓｐｅｃｕｒｕｓａｅｑｕａｌｉｓ）、ブラックグラス（Ａｌｏｐｅｃｕｒｕｓｍｙｏｓｕｒｏｉｄｅｓ）、カラスムギ（Ａｖｅｎａｆａｔｕａ）、セイバンモロコシ(Sorghum halepense), Shattercane (Sorghum bulgare), Sorgham arundinaceum, Shibamugi (Agropylron repens), Festuca perennial (Lolium multiflorum) ), Aretinochahiki (Bromus sterilis), Suzumenochahiki (Bromus japonicus), Karasunochahiki (Bromus secalinus), Umanochahiki (Bromus tectorum), Hosonogemugi (Hordeum jabac) (Phalaris minor), Silky bentgrass (Apera spica-venti), Okusakibi (Pancum dichotomiflorum), Texas Panicum (Panicum texanum), Guineakibi (Panicum maximum), Merikennikkibi (Brachiaria) （Ｂｒａｃｈｉａｒｉａｐｌａｎｔａｇｉｎｅａ）、スリナムグラス（Ｂｒａｃｈｉａｒｉａｄｅｃｕｍｂｅｎｓ）、パリセードグラス（Ｂｒａｃｈｉａｒｉａｂｒｉｚａｎｔｈａ）、コロンビアグラス（Ｂｒａｃｈｉａｒｉａｈｕｍｉｄｉｃｏｌａ）、パラグラス（Ｕｒｏｃｈｌｏａｍｕｔｉｃａ）、シンクリノイガ（Ｃｅｎｃｈｒｕｓｅｃｈｉｎａｔｕｓ）、ヒメクリノイガ（Ｃｅｎｃｈｒｕｓｐａｕｃｉｆｌｏｒｕｓ）、ナルコビエ（Ｅｒｉｏｃｈｌｏａｖｉｌｌｏｓａ）、アフリカヒゲシバ（Ｃｈｌｏｒｉｓｇａｙａｎａ）、オヒゲシバ（Ｃｈｌｏｒｉｓｖｉｒｇａｔａ）、オオニワホコリ（Ｅｒａｇｒｏｓｔｉｓｐｉｌｏｓａ）、エラグロスティスプラナ（Ｅｒａｇｒｏｓｔｉｓｐｌａｎａ）、ルビーガヤ（Ｒｈｙｎｃｈｅｌｉｔｒｕｍｒｅｐｅｎｓ）、タツノツメガヤ（Ｄａｃｔｙｌｏｃｔｅｎｉｕｍａｅｇｙｐｔｉｕｍ）、タイワンアイアシ（Ｉｓｃｈａｅｍｕｍｒｕｇｏｓｕｍ）、チゴザサ（Ｉｓａｃｈｎｅｇｌｏｂｏｓａ）、イネ（Ｏｒｙｚａｓａｔｉｖａ）、アメリカスズメノヒエ（Ｐａｓｐａｌｕｍｎｏｔａｔｕｍ）、コースタルサンドパスパルム（Ｐａｓｐａｌｕｍｍａｒｉｔｉｍｕｍ）、キシュウスズメノヒエ（Ｐａｓｐａｌｕｍｄｉｓｔｉｃｈｕｍ）、キクユグラス（Ｐｅｎｎｉｓｅｔｕｍｃｌａｎｄｅｓｔｉｎｕｍ）、ホソバチカラシバ（Ｐｅｎｎｉｓｅｔｕｍｓｅｔｏｓｕｍ）、ツノアイアシ（Ｒｏｔｔｂｏｅｌｌｉａｃｏｃｈｉｎｃｈｉｎｅｎｓｉｓ ), Azegaya (Leptochloa chinensis), Oniazegaya (Leptochloa fascillalis), Itozegaya (Leptochloa panicea), Hokiazegaya (Leptochloa brachiaria), Amazon ｅｓ）、アシカキ（Ｌｅｅｒｓｉａｊａｐｏｎｉｃａ）、タイワンアシカキ（Ｌｅｅｒｓｉａｈｅｘａｎｄｒａ）、サヤヌカグサ（Ｌｅｅｒｓｉａｓａｙａｎｕｋａ）、エゾノサヤヌカグサ（Ｌｅｅｒｓｉａｏｒｙｚｏｉｄｅｓ）、ウキガヤ（Ｇｌｙｃｅｒｉａｌｅｐｔｏｒｒｈｉｚａ）、ムツオレグサ（Ｇｌｙｃｅｒｉａａｃｕｔｉｆｌｏｒａ）、ドジョウツナギ（Ｇｌｙｃｅｒｉａｍａｘｉｍａ）、コヌカグサ（Ａｇｒｏｓｔｉｓｇｉｇａｎｔｅａ）、ハイコヌカグサ（Ａｇｒｏｓｔｉｓｓｔｏｌｏｎｉｆｅｒａ）、ギョウギシバ（Ｃｙｎｏｄｏｎｄａｃｔｙｌｏｎ）、カモガヤ（Ｄａｃｔｙｌｉｓｇｌｏｍｅｒａｔａ）、ムカデシバ（Ｅｒｅｍｏｃｈｌｏａｏｐｈｉｕｒｏｉｄｅｓ）、オニウシノケグサ（Ｆｅｓｔｕｃａａｒｕｎｄｉｎａｃｅａ）、オオウシノケグサ（Ｆｅｓｔｕｃａｒｕｂｒａ）、チガヤ（Ｉｍｐｅｒａｔａｃｙｌｉｎｄｒｉｃａ）、ススキ（ Miscanthus sinensis, Switchglass (Panicum virgatum), Nosiba (Zoysia japonica), Luziola peruviana, Rubygrass (Melinis repens), Spartan Anglica (Spartina Anglica).

Sedge family Weeds (Cyperaceae):
カヤツリグサ（Ｃｙｐｅｒｕｓｍｉｃｒｏｉｒｉａ）、コゴメガヤツリ（Ｃｙｐｅｒｕｓｉｒｉａ）、クグガヤツリ（Ｃｙｐｅｒｕｓｃｏｍｐｒｅｓｓｕｓ）、タマガヤツリ（Ｃｙｐｅｒｕｓｄｉｆｆｏｒｍｉｓ）、ヒナガヤツリ（Ｃｙｐｅｒｕｓｆｌａｃｃｉｄｕｓ）、アゼガヤツリ（Ｃｙｐｅｒｕｓｇｌｏｂｏｓｕｓ）、アオガヤツリ（Ｃｙｐｅｒｕｓｎｉｐｐｏｎｉｃｓ）、キンガヤツリ（Ｃｙｐｅｒｕｓｏｄｏｒａｔｕｓ）、ミズガヤツリ（Ｃｙｐｅｒｕｓｓｅｒｏｔｉｎｕｓ）、ハマスゲ（Ｃｙｐｅｒｕｓｒｏｔｕｎｄｕｓ）、キハマスゲ（Ｃｙｐｅｒｕｓｅｓｃｕｌｅｎｔｕｓ）、ヒメクグ（Ｋｙｌｌｉｎｇａｇｒａｃｉｌｌｉｍａ）、アイダクグ（Ｋｙｌｌｉｎｇａｂｒｅｖｉｆｏｌｉａ）、ヒデリコ（Ｆｉｍｂｒｉｓｔｙｌｉｓｍｉｌｉａｃｅａ）、テンツキ（Ｆｉｍｂｒｉｓｔｙｌｉｓｄｉｃｈｏｔｏｍａ）、マツバイ（Ｅｌｅｏｃｈａｒｉｓａｃｉｃｕｌａｒｉｓ）、クログワイ（Ｅｌｅｏｃｈａｒｉｓｋｕｒｏｇｕｗａｉ）、ホタルイ（Ｓｃｈｏｅｎｏｐｌｅｃｔｉｅｌｌａｈｏｔａｒｕｉ）、イヌホタルイ（Ｓｃｈｏｅｎｏｐｌｅｃｔｉｅｌｌａｊｕｎｃｏｉｄｅｓ）、タイワンヤマイ（Ｓｃｈｏｅｎｏｐｌｅｃｔｉｅｌｌａｗａｌｌｉｃｈｉｉ）、ヒメカンガレイ（Ｓｃｈｏｅｎｏｐｌｅｃｔｉｅｌｌａｍｕｃｒｏｎａｔｕｓ）、カンガレイ（Ｓｃｈｏｅｎｏｐｌｅｃｔｉｅｌｌａｔｒｉａｎｇｕｌａｔｕｓ）、シズイ（Ｓｃｈｏｅｎｏｐｌｅｃｔｉｅｌｌａｎｉｐｐｏｎｉｃｕｓ）、サンカクイ（Ｓｃｈｏｅｎｏｐｌｅｃｔｉｅｌｌａｔｒｉｑｕｅｔｅｒ）、コウキヤガラ（Ｂｏｌｂｏｓｃｈｏｅｎｕｓｋｏｓｈｅｖｎｉｋｏｖｉｉ ), Nutsedge (Bolboschoenus fluviatilis), Futoi (Scirpus tabernaemontani).

Equisetaceae: Equisetaceae:
Horsetail (Equisetum palustre), Equisetum palustre.

Salvinia seaweed:
Salvinia natans.

Azollaceae:
Azolla japonica, Azollaim bricata, Salvinia natanas, Azolla cristata.

Marsilea quadrifolia (Marsilea quadrifolia):
Water clover (Marsilea quadrifolia).

Ricciaceae:
Ricciocarpos natans.

Rosaceae:
Lady's mantle (Alchemilla monticola).

Ranunculaceae:
Ranunculus silicatus, Ranunculus sardous.

Fumariaceae Weeds:
Fumitory (Fumia officeis).

Characeae:
Chara braunii.

Eriocaulaceae:
Eriocaulon cinereum.

Zygnemaceae:
Spirogyra arcla.

others:
Sucking branches of filamentous algae (Pitophora, Cladophora), moss, liverworts, hornworts, cyanobacteria, ferns, perennial crops (fruits, stones, berries, berries, citrus fruits, hops, grapes, etc.) (Sucker).

For the above weeds, the variation within the species is not particularly limited. That is, those having reduced sensitivity to a specific herbicide (also referred to as exhibiting resistance) are also included. The decrease in susceptibility may be due to a mutation at the target site (point mutation) or a factor other than the point mutation (non-point mutation). Regarding point of action mutations, mutations in the nucleic acid sequence portion (open reading frame) corresponding to the amino acid sequence of the protein cause amino acid substitution in the protein at the target site, deletion of the suppressor sequence in the promoter region, and enhancer sequence. This includes those in which the protein at the target site is expressed in excess or decrease due to amplification of the gene or mutation such as increase or decrease in the number of copies of the gene. Non-point mutations include metabolic enhancement, absorption deficiency, subsequent deficiency, and extrasystem excretion. Factors that enhance metabolism include those with increased activity of metabolic enzymes such as cytochrome P450 monooxygenase, arylacylamidase, esterase, and glutathione S-transferase. Out-of-system discharge includes transport to vacuoles by an ABC transporter.

Examples of herbicide-resistant weeds include 5-enolpyrvir simirate-3-phosphate (EPSP) synthase inhibitor resistance such as glyphosate, and hormonal-disrupting herbicides such as 2,4-D and dicamba. Resistance, acetolactic synthase (ALS) inhibitor resistance, acetyl CoA carboxylase (ACCace) inhibitor resistance, protoporphyllinogen oxidase (PPO) inhibitor resistance, auxin herbicide resistance, 4-hydroxy Phenylpyruvate dioxygenase (4-HPPD) inhibitor resistance, photochemical system II inhibitor resistance, photochemical system I electron converter resistance, carotenoid biosynthesis inhibitor resistance, glutamine synthase inhibitor resistance, phytoene elimination Saturated enzyme system (PDS) inhibitor resistance, fatty acid biosynthesis inhibitor resistance, ultra-long chain fatty acid elongation enzyme (VLCFAE) inhibitor resistance, auxin transport inhibitor resistance, dihydropteroic acid (DHP) synthase Inhibitor resistance, cellulose synthase inhibitor resistance, microtube polymerization enzyme inhibitor resistance, thread splitting / microtube formation inhibitor resistance and the like can be mentioned.

Resistant weeds are two or more of the above groups (2 groups arbitrarily selected, 3 groups arbitrarily selected, 4 groups arbitrarily selected, 5 groups, 6 groups, 7 groups arbitrarily selected, Even resistant weeds (stacked) that also have resistance to (group 8) are effectively controlled. Examples of stacked resistant weeds are acetolactic synthase (ALS) inhibitors, protoporphyllinogen oxidase (PPO) inhibitors, 4-hydroxyphenylpyruvate dioxygenase (4-HPPD) inhibitors, photochemical system II. Inhibitors and water hemps resistant to all of 2,4-D are known, but they are also effectively controlled. The above stack may be a combination of action point mutations, a combination of non-point mutations, or a combination of action mutations and non-point mutations.

The herbicide of the present invention and the pesticide composition containing the herbicide of the present invention are simultaneously or divided into useful plants, places where useful plants are to be grown or where they are growing, or non-agricultural land. When applying, apply once or multiple times. Weeds may have already grown in the plant or the plant cultivated area, or may be before the outbreak.

The herbicide of the present invention and the pesticide composition containing the herbicide of the present invention are simultaneously or divided into useful plants, places where useful plants are to be grown or where they are growing, or non-agricultural land. Examples of the method of application include foliage treatment, soil treatment, root treatment, shower treatment, smoke treatment, water surface treatment, seed treatment and hydroponic liquid treatment.

As the foliage treatment, for example, a pesticide composition containing the herbicide of the present invention and the herbicide of the present invention can be applied to foliage, tree stems, fruits, flowers (including before, during, and after flowering), ears, or the entire plant. There is a method of treating the surface of.

Examples of soil treatment include soil spraying, soil miscibility, and chemical irrigation into the soil. In addition, as places for soil treatment, for example, planting holes, crops, near planting holes, near crops, the entire cultivation area, near the plant area, between stocks, under the trunk, main trunk ridges, soil cultivation, nursery boxes, seedling raising. Examples include trays and nurseries. Examples of the treatment time include pre-sowing, sowing, post-sowing, seedling raising period, pre-planting, planting, and post-sowing growing period. Further, in the above soil treatment, the herbicide of the present invention and the pesticide composition containing the herbicide of the present invention may be mixed with the irrigation liquid, for example, to an irrigation facility (irrigation tube, irrigation pipe, sprinkler, etc.). Injection, mixing in interstitial flooded liquid, mixing in hydroponic liquid, etc. can be mentioned. Further, the irrigation solution and the active ingredient can be mixed in advance and treated by using, for example, the above irrigation method or an appropriate irrigation method such as watering or flooding.

The root treatment includes, for example, a method of immersing the root in a chemical solution containing the herbicide of the present invention and a pesticide composition containing the herbicide of the present invention, and a pesticide composition containing the herbicide of the present invention and the herbicide of the present invention. Examples thereof include a method of adhering a solid preparation containing a substance to the root of a plant.

Examples of the shower treatment include a method of showering a diluted solution of a pesticide composition containing the herbicide of the present invention and the herbicide of the present invention on the foliage of a plant.

Examples of the smoke treatment include a method in which a diluted solution of the herbicide of the present invention and a pesticide composition containing the herbicide of the present invention is made into a mist and scattered in the air to adhere to the foliage of a plant or the like. ..

Examples of the water surface treatment include a method of spraying a chemical solution or a solid preparation containing the herbicide of the present invention and the pesticide composition containing the herbicide of the present invention on a paddy field in a flooded state.

Examples of the seed treatment include treatment of the herbicide of the present invention on seeds or vegetative reproduction organs and the treatment of a pesticide composition containing the herbicide of the present invention. The above-mentioned vegetative organs include seed potatoes in particular.

The hydroponic solution treatment is, for example, a method of mixing or mixing a chemical solution or a solid preparation containing the herbicide of the present invention and a pesticide composition containing the herbicide of the present invention with the hydroponic solution (hydroponic solution miscibility treatment, water). Treatment of mixing cultivated liquid, etc.) and the like.

The herbicide of the present invention and the pesticide composition containing the herbicide of the present invention can also be applied by spot treatment. Spot treatment is a concept opposite to the uniform treatment of the herbicide of the present invention and the pesticide composition containing the herbicide of the present invention, and is a place where weeds are growing or where weeds are generated. It means a treatment of selectively spraying the herbicide of the present invention and the pesticide composition containing the herbicide of the present invention to a possible place. By "treating to a place" is meant treating a plant or soil that has or may have weeds. In addition, spot treatment is not considered only when all of the places where weeds are growing or where weeds may grow in a continuous cultivation area are selectively treated. That is, when a part of the cultivated area is subjected to surface treatment, or a part of the place where weeds are growing or where weeds may grow, the herbicide of the present invention and the herbicide of the present invention are used. Even if it is not treated with the pesticide composition containing it, it is included in the spot treatment if there is a spot-treated place in the continuous cultivation area.

Next, the method for producing the compound of the present invention, the formulation method, and the use thereof will be described in detail in the following examples, but the present invention is not limited to these examples.

The melting point, which is the physical property value of the compound of the present invention, was measured with an MP-500V trace melting point measuring device manufactured by Yanaco. The refractive index was measured using an Abbe refractometer manufactured by Atago. ¹ The 1 H NMR spectrum was measured using JEM-LA400 (400 MHz) or JNM-ECS300 (300 MHz) manufactured by JEOL Ltd. with tetramethylsilane (TMS) as an internal standard.

Further, a production example of a production intermediate of the compound of the present invention is also described.

[Example 1]
Production of 3-chloro-7- [(5-chloropyrimidine-2-yl) oxy] -1- (4,4,4-trifluorobutyl) -1H-indole (compound number: A-0032 of the present invention) :
(1) Production of 7-[(5-chloropyrimidine-2-yl) oxy] -1H-indole (compound number: A-0001 of the present invention):
To a mixture of 0.75 g (5.63 mmol) of 1H-indole-7-ol and 10 mL of N, N-dimethylformamide, 0.27 g of sodium hydride (6.19 mmol, converted as 55% purity) was added under ice cooling. , Stirred for 5 minutes while maintaining the same temperature. Then, under ice-cooling, 1.01 g (6.78 mmol) of 2,5-dichloropyrimidine was added, and the mixture was stirred at room temperature for 24 hours. After completion of the reaction, 1N hydrochloric acid was added to make the reaction acidic, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 20: 1 to 3: 1) to obtain 0.87 g (yield 63%) of the desired product. rice field.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 8.50 (2H, s), 8.24 (1H, brass), 7.56 (1H, d), 7.20 (1H, 1H, t), 7.14 (1H, t), 7.05 (1H, d), 6.62 (1H, dd)

(2) Production of 7-[(5-chloropyrimidine-2-yl) oxy] -1- (4,4,4-trifluorobutyl) -1H-indole (compound number: A-0004 of the present invention):
1 in a mixture of 7-[(5-chloropyrimidine-2-yl) oxy] -1H-indole 0.33 g (1.34 mmol), potassium carbonate 0.37 g (2.68 mmol), N, N-dimethylformamide 5 mL , 1,1-Trifluoro-4-iodobutane 0.38 g (1.60 mmol) was added, and the mixture was stirred at 80 ° C. for 11 hours, and then 1,1,1-trifluoro-4-iodobutane 0.38 g (1.60 mmol) was added. ), 0.87 g (2.67 mmol) of cesium carbonate was further added, and the mixture was stirred at 80 ° C. for 10.5 hours. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 100: 1 to 4: 1) to obtain 0.28 g (yield 59%) of the desired product. rice field.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 8.51 (2H, s), 7.53 (1H, d), 7.11 (1H, t), 7.02 (1H, 1H, d), 6.96 (1H, d), 6.55 (1H, d), 4.21 (2H, t), 2.03-1.96 (4H, m)

(3) 3-Chloro-7-[(5-chloropyrimidine-2-yl) oxy] -1- (4,4,4-trifluorobutyl) -1H-indole (Compound number of the present invention: A-0032) )Manufacturing of:
7-[(5-Chloropyrimidine-2-yl) oxy] -1- (4,4,4-trifluorobutyl) -1H-indole 0.20 g (0.56 mmol) in a mixture of 8 mL of acetonitrile and ice-cooled Below, 0.08 g (0.60 mmol) of N-chlorosuccinic acid imide was added, and the mixture was stirred for 3 hours while maintaining the same temperature, and then stirred at room temperature for 18 hours. After completion of the reaction, an aqueous sodium thiosulfate solution was added, the mixture was extracted with dichloromethane, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 20: 1 to 6: 1) to obtain 0.18 g (yield 82%) of the desired product. rice field.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 8.51 (2H, s), 7.54 (1H, d), 7.19 (1H, t), 7.04-7. 01 (2H, m), 4.18 (2H, t), 2.02-1.96 (4H, m)

[Example 2]
7-[(5-Chloropyrimidine-2-yl) oxy] -1- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} -1H-indazole-3-carbonitrile ( Production of compound number: B-0376) of the present invention:
(1) Production of 3-iodo-7-methoxy-1H-indazole:
A mixture of 7.51 g (51.1 mmol) of 7-methoxy-1H-indazole, 16.1 g (71.6 mmol) of N-iodosuccinic acid imide and 100 mL of isopropyl alcohol was stirred at 45 ° C. for 7 hours. After allowing to cool at room temperature, the solvent is concentrated under reduced pressure, the residue is purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 5: 1), and the target product is 8.75 g (yield 63). %)Obtained.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 7.13 (1H, t), 7.08 (1H, d), 6.80 (1H, d), 3.98 (3H, s)

(2) Production of 3-iodo-7-methoxy-1- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} -1H-indazole:
3-Iodine-7-methoxy-1H-indazole 2.39 g (8.72 mmol), 1- (2-bromoethyl) -3- (trifluoromethyl) -1H-pyrazole 2.53 g (9.46 mmol), potassium carbonate A mixture of 1.45 g (10.5 mmol) and 20 mL of N, N-dimethylformamide was stirred at 100 ° C. for 6 hours. After completion of the reaction, ethyl acetate was added, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 5: 1) to obtain 2.56 g (yield 67%) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 7.06 (1H, t), 7.00 (1H, d), 6.73 (1H, d), 6.66 (1H, 1H, d), 6.22 (1H, d), 5.08 (2H, t), 4.67 (2H, t)

(3) Production of 3-iodo-1- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} -1H-indazole-7-ol:
3-Iodo-7-Methoxy-1- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} -1H-indazole 1.00 g (2.29 mmol) in a mixture of 20 mL of dichloromethane , 6.90 mL of boron tribromide (1 mol / L dichloromethane solution) was added under ice-cooling, and the mixture was stirred at room temperature for 13 hours. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and used as it was in the next step without purification.

(4) 7-[(5-Chloropyrimidine-2-yl) oxy] -3-iodo-1- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} -1H- Production of indazole (compound number of the present invention: B-034):
Crude 3-iodo-1- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} -1H-indazole-7-ol, 2,5-dichloropyrimidine 0.44 g (2) A mixture of .95 mmol), 0.41 g (2.97 mmol) potassium carbonate and 20 mL of N, N-dimethylformamide was stirred at 100 ° C. for 7 hours. After completion of the reaction, ethyl acetate was added, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 10: 1) to obtain 1.26 g (yield quantitative, 2 steps) of the desired product. ..

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 8.50 (2H, s), 7.41 (1H, d), 7.39 (1H, d), 7.25 (1H, t), 7.16 (1H, d), 6.33 (1H, d), 4.85 (2H, t), 4.62 (2H, t)

(5) 7-[(5-Chloropyrimidine-2-yl) oxy] -1- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} -1H-indazole-3- Production of Carbonitrile (Compound No. B-0376 of the present invention):
7-[(5-Chloropyrimidine-2-yl) oxy] -3-iodo-1- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} -1H-indazole 0. A mixture of 70 g (1.31 mmol), 0.36 g (4.02 mmol) of copper (I) cyanide and 5 mL of N, N-dimethylacetamide was stirred at 140 ° C. for 16 hours. After allowing to cool at room temperature, the insoluble material is filtered through Celite, the solvent is distilled off under reduced pressure, and the residue is purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4: 1) for the purpose. The product was obtained in an amount of 0.35 g (yield 62%).

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 8.52 (2H, s), 7.73 (1H, d), 7.38 (1H, t), 7.33 (1H, d), 7.23 (1H, d), 6.36 (1H, d), 4.96 (2H, t), 4.70 (2H, t)

[Example 3]
7-[(5-Chloropyrimidine-2-yl) oxy] -3-methoxy-1- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} -1H-indazole (book) Production of compound number B-0384) of the invention:
(1) Production of 7- (benzyloxy) -3-iodo-1H-indazole:
10.14 g (45.2 mmol) of 7-methoxy-1H-indazole, 17.21 g (67.8 mmol) of iodine, 8.41 g of potassium hydroxide (127.0 mmol, converted as 85% purity), N, N-dimethylformamide. The 200 mL mixture was stirred at room temperature for 4 hours. After completion of the reaction, an aqueous sodium thiosulfate solution was added, and the mixture was further stirred at room temperature for 1 hour. Ethyl acetate was added, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 15.85 g (quantitative yield) of the crude target product.

(2) Production of 7- (benzyloxy) -3-iodo-1- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} -1H-indazole:
7- (benzyloxy) -3-iodo-1H-indazole 7.86 g (22.4 mmol), 1- (2-bromoethyl) -3- (trifluoromethyl) -1H-pyrazole 5.99 g (24.6 mmol) , 3.40 g (24.6 mmol) of potassium carbonate and 100 mL of N, N-dimethylformamide were stirred at 80 ° C. for 6 hours. After completion of the reaction, ethyl acetate was added, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 5: 1) to obtain 8.56 g (yield 74%) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 7.45-7.39 (5H, m), 7.08-7.04 (2H, m), 6.81 (1H, d) ), 6.70 (1H, d), 6.25 (1H, d), 5.11 (2H, s), 5.05 (2H, t), 4.61 (2H, t)

(3) Production of 7- (benzyloxy) -3-methoxy-1- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} -1H-indazole:
7- (benzyloxy) -3-iodo-1- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} -1H-indazole 1.00 g (1.95 mmol), cesium carbonate 1.27 g (3.90 mmol), 0.08 g (0.42 mmol) of copper (I) iodide, 3,4,7,8-tetramethyl-1,10-phenanthroline 0.18 (0.76 mmol), methanol The 30 mL mixture was stirred at 120 ° C. for 6 hours under a nitrogen atmosphere. After allowing to cool at room temperature, the insoluble material is filtered through Celite, the solvent is distilled off under reduced pressure, and the residue is purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 10: 1) to obtain the desired product. 0.78 g (yield 96%) was obtained.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 7.19 (1H, t), 7.13-6.93 (9H, m), 5.22 (2H, s), 4. 17 (2H, t), 3.53 (2H, t), 3.53 (3H, s)

(4) Production of 3-Methoxy-1- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} -1H-indazole-7-ol:
7- (benzyloxy) -3-methoxy-1- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} -1H-indazole 0.78 g (1.87 mmol), 10% A mixture of 0.16 g of Pd / C and 50 mL of tetrahydrofuran was stirred at room temperature for 5 hours under a hydrogen atmosphere (normal pressure). After completion of the reaction, the mixture was filtered through Celite, and the solvent was distilled off under reduced pressure to obtain 0.60 g (yield 98%) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 7.15 (1H, d), 7.02 (1H, d), 6.83 (1H, t), 6.68 (1H, 1H, d), 6.31 (1H, d), 4.94 (2H, t), 4.62 (2H, t), 4.04 (3H, s)

(5) 7-[(5-Chloropyrimidine-2-yl) oxy] -3-methoxy-1- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} -1H- Production of Indazole (Compound No. B-0384 of the present invention):
3-Methoxy-1- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} -1H-indazole-7-ol 0.18 g (0.55 mmol), 2,5-dichloro A mixture of 0.11 g (0.74 mmol) of pyrimidine, 0.10 g (0.72 mmol) of potassium carbonate and 5 mL of N, N-dimethylformamide was stirred at 80 ° C. for 4 hours. After completion of the reaction, ethyl acetate was added, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 8: 1) to obtain 0.15 g (yield 62%) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 8.49 (2H, s), 7.54 (1H, d), 7.15 (1H, d), 7.11 (1H, 1H, d), 7.06 (1H, t), 6.32 (1H, d), 4.60 (2H, t), 4.53 (2H, t), 4.04 (3H, s)

[Example 4]
7-[(5-Chloropyrimidine-2-yl) oxy] -1- (4,4,4-trifluorobutyl) -3- (trifluoromethyl) -1H-indazole (Compound number of the present invention: B- 0328) Manufacture:
(1) Production of 2,2,2-trifluoro-1- [2-fluoro-3- (methoxymethoxy) phenyl] ethane-1-one:
To a mixture of 2.39 g (23.6 mmol) of diisopropylamine and 20 mL of tetrahydrofuran was added dropwise 14.8 mL of n-butyllithium (1.6 mol / L hexane solution) at −78 ° C. under a nitrogen atmosphere. After completion of the dropping, the mixture was stirred at 0 ° C. for 30 minutes, and then 3.12 g (20.0 mmol) of 1-fluoro-2- (methoxymethoxy) benzene was added dropwise at −78 ° C. After completion of the dropping, the mixture was stirred for 1 hour while maintaining the same temperature. 3.50 g (24.6 mmol) of ethyl trifluoroacetate was added dropwise to the above reaction mixture while maintaining the same temperature, and the mixture was further stirred at 0 ° C. for 2 hours. After completion of the reaction, 2N hydrochloric acid was added, the mixture was extracted with ethyl acetate, the obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4: 1) to obtain 1.82 g (yield 36%) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 7.57-7.47 (2H, m), 7.22 (1H, t), 5.26 (2H, s), 3. 54 (3H, s)

(2) Production of 7- (methoxymethoxy) -3- (trifluoromethyl) -1H-indazole:
2,2,2-Trifluoro-1- [2-fluoro-3- (methoxymethoxy) phenyl] ethane-1-one 1.00 g (3.97 mmol), anhydrous hydrazine 2.53 g (79.3 mmol), 1 , 4-Dioxane 20 mL mixture was stirred at 100 ° C. for 5 hours. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with 3N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 2: 1) to obtain 0.68 g (yield 70%) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 7.50 (1H, d), 7.20 (1H, t), 7.10 (1H, d), 5.34 (2H, s), 3.61 (3H, s)

(3) Production of 7- (methoxymethoxy) -1- (4,4,4-trifluorobutyl) 3- (trifluoromethyl) -1H-indazole:
7- (Methoxymethoxy) -3- (trifluoromethyl) -1H-indazole 0.30 g (1.22 mmol), 1,1,1-trifluoro-4-iodobutane 0.35 g (1.47 mmol), potassium carbonate A mixture of 0.20 g (1.45 mmol) and 10 mL of N, N-dimethylformamide was stirred at 100 ° C. for 5 hours. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 5: 1) to obtain 0.38 g (yield 88%) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 7.43 (1H, d), 7.17 (1H, t), 7.08 (1H, d), 5.38 (2H, s), 4.78 (2H, t), 3.55 (3H, s), 2.26-2.15 (4H, m)

(4) Production of 1- (4,4,4-trifluorobutyl) 3- (trifluoromethyl) -1H-indazole-7-ol:
7- (Methoxymethoxy) -1- (4,4,4-trifluorobutyl) 3- (trifluoromethyl) -1H-indazole 0.38 g (1.07 mmol), 3N hydrochloric acid 1.78 mL (5.34 mmol) , The mixture of 5 mL of tetrahydrofuran was stirred at 50 ° C. for 8 hours. After completion of the reaction, ethyl acetate was added, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 1) to obtain 0.19 g (yield 57%) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 7.39 (1H, d), 7.09 (1H, t), 6.74 (1H, d), 4.78 (2H, t), 2.22-2.11 (4H, m)

(5) 7-[(5-Chloropyrimidine-2-yl) oxy] -1- (4,4,4-trifluorobutyl) -3- (trifluoromethyl) -1H-indazole (compound number of the present invention). : B-0328) Manufacture:
1- (4,4,4-trifluorobutyl) 3- (trifluoromethyl) -1H-indazole-7-ol 0.18 g (0.58 mmol), 2,5-dichloropyrimidine 0.11 g (0.74 mmol) ), Potassium carbonate 0.11 g (0.80 mmol), N, N-dimethylformamide 10 mL mixture was stirred at 80 ° C. for 3 hours. After completion of the reaction, ethyl acetate was added, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 5: 1) to obtain 0.22 g (yield 90%) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 8.54 (2H, s), 7.76 (1H, d), 7.32 (1H, t), 7.27 (1H, d), 4.55 (2H, t), 2.10-2.05 (4H, m)

[Example 5]
7-[(5-Chloropyrimidine-2-yl) oxy] -1- (4,4,4-trifluorobutyl) -1H-benzo [d] [1,2,3] triazole (compound number of the present invention) : C-0002) Manufacture:
(1) Production of 2-methoxy-6-nitro-N- (4,4,4-trifluorobutyl) aniline:
2-Methoxy-6-nitroaniline 3.37 g (20.0 mmol), 1,1,1-trifluoro-4-iodobutane 5.71 g (24.0 mmol), sodium hydride 1.12 g (28.0 mmol, purity) A mixture of 100 mL of N, N-dimethylformamide (converted as 60%) was stirred at 100 ° C. for 7 hours. After completion of the reaction, ethyl acetate was added, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 10: 1) to obtain 3.78 g (yield 68%) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 7.74 (1H, d), 6.94 (1H, d), 6.68 (1H, t), 3.86 (3H, s), 3.62 (2H, t), 2.23-2.14 (2H, m), 1.93-1.85 (2H, m)

(2) Production of 6-methoxy ^- N1- (4,4,4-trifluorobutyl) benzene-1,2-dianiline:
A mixture of 2-methoxy-6-nitro-N- (4,4,4-trifluorobutyl) aniline 2.45 g (8.81 mmol), 10% Pd / C 0.25 g, and methanol 100 mL under a hydrogen atmosphere (normal pressure). ), Stirred at room temperature for 16 hours. After completion of the reaction, the mixture was filtered through Celite, and the solvent was distilled off under reduced pressure to obtain 2.17 (yield 99%) of the crude target product.

^{1 1} H-NMR data (300 MHz, DMSO-d ₆ / TMSδ (ppm)): 6.66 (1H, t), 6.29 (1H, d), 6.22 (1H, d), 4.63 ( 2H, brs), 3.71 (3H, s), 2.94-2.86 (2H, m), 2.41-2.26 (2H, m), 1.66-1.56 (2H, m) m)

(3) Production of 7-methoxy-1- (4,4,4-trifluorobutyl) -1H-benzo [d] [1,2,3] triazole:
In a mixture of 6-methoxy-N ^1- (4,4,4-trifluorobutyl) benzene-1,2-dianiline 0.97 g (3.91 mmol), sulfuric acid 1.34 g (13.7 mmol), and water 50 mL. Under ice-cooling, 0.54 g (7.83 mmol) of sodium nitrite was added, and the mixture was stirred at room temperature for 23 hours. After completion of the reaction, ethyl acetate was added, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 1) to obtain 0.70 g (yield 69%) of the desired product.

^{1 1} H-NMR data (300 MHz, DMSO-d ₆ / TMSδ (ppm)): 7.37 (1H, d), 7.33 (1H, t), 7.05 (1H, d), 4.51 ( 2H, t), 3.98 (3H, s), 3.02-2.93 (2H, m), 2.03-1.96 (2H, m)

(4) Production of 7-methoxy-1- (4,4,4-trifluorobutyl) -1H-benzo [d] [1,2,3] triazole:
7-methoxy-1- (4,4,4-trifluorobutyl) -1H-benzo [d] [1,2,3] Triazole 0.70 g (2.70 mmol) in a mixture of 20 mL of dichloromethane under ice cooling. , 13.5 mL of boron tribromide (1 mol / L dichloromethane solution) was added, and the mixture was stirred at room temperature for 15 hours. After completion of the reaction, water was added, the mixture was extracted with ethyl acetate, the obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 0.56 g (yield 85%) of the crude target product.

^{1 1} H-NMR data (300 MHz, DMSO-d ₆ / TMSδ (ppm)): 10.77 (1H, brs), 7.42 (1H, d), 7.17 (1H, t), 6.82 ( 1H, d), 4.87 (2H, t), 2.35-2.27 (2H, m), 2.22-2.13 (2H, m)

(5) 7-[(5-Chloropyrimidine-2-yl) oxy] -1- (4,4,4-trifluorobutyl) -1H-benzo [d] [1,2,3] triazole (the present invention) Compound No .: C-0002) Manufacture:
7-Methoxy-1- (4,4,4-trifluorobutyl) -1H-benzo [d] [1,2,3] triazole 0.35 g (1.43 mmol), 2,5-dichloropyrimidine 0.30 g A mixture of (2.01 mmol), 0.28 g (2.03 mmol) of potassium carbonate and 10 mL of N, N-dimethylformamide was stirred at 80 ° C. for 3 hours. After completion of the reaction, ethyl acetate was added, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 5: 1) to obtain 0.38 g (yield 74%) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 8.54 (2H, s), 7.99 (1H, d), 7.41 (1H, t), 7.32 (1H, d), 4.71 (2H, t), 2.19-2.11 (4H, m)

[Example 6]
7-[(5-Chloropyrimidine-2-yl) oxy] -2-methyl-1- (4,4,4-trifluorobutyl) -1H-benzo [d] imidazole (compound number of the present invention: D- 0010) Manufacture:
(1) Production of 7-methoxy-2-methyl-1- (4,4,4-trifluorobutyl) -1H-benzo [d] imidazole:
A mixture of 0.88 g (3.54 mmol) of 6-methoxy-N- ^1- (4,4,4-trifluorobutyl) benzene-1,2-diamine, 5 mL of acetic acid and 10 mL of triethyl orthoacetate was heated to reflux for 15 hours. After allowing to cool at room temperature, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4: 1 to 1:20) to obtain the desired product. 46 g (yield 48%) was obtained.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 7.30 (1H, d), 7.13 (1H, t), 6.68 (1H, d), 4.40 (2H, t), 3.95 (3H, s), 2.57 (3H, s), 2.25-2.02 (4H, m)

(2) Production of 2-Methyl-1- (4,4,4-trifluorobutyl) -1H-benzo [d] imidazole-7-ol:
7-Methoxy-2-methyl-1- (4,4,4-trifluorobutyl) -1H-benzo [d] imidazole 0.46 g (1.69 mmol), dichloromethane 5 mL mixture, under ice-cooling, three odors 10.10 mL (10.10 mmol) of boron tribromide (about 1 mol / L dichloromethane solution) was added, and the mixture was stirred at room temperature for 3 days. After completion of the reaction, a saturated aqueous sodium hydrogen carbonate solution was added and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 0.44 g (quantitative yield) of the crude target product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 7.25 (1H, d), 7.02 (1H, t), 6.66 (1H, d), 4.49 (2H, t), 2.61 (3H, s), 2.28-2.13 (4H, m)

(3) 7-[(5-Chloropyrimidine-2-yl) oxy] -2-methyl-1- (4,4,4-trifluorobutyl) -1H-benzo [d] imidazole (compound number of the present invention). : D-0010) Manufacture:
2-Methyl-1- (4,4,4-trifluorobutyl) -1H-benzo [d] imidazole-7-ol 0.20 g (0.77 mmol), 2,5-dichloropyrimidine 0.14 g (0. A mixture of 94 mmol), 0.14 g (1.01 mmol) of potassium carbonate and 5 mL of N, N-dimethylformamide was stirred at 80 ° C. for 4.5 hours. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 3: 2 to 1: 4) to obtain 0.18 g (yield 63%) of the desired product. rice field.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 8.53 (2H, s), 7.60 (1H, d), 7.24 (1H, t), 7.02 (1H, 1H, d), 4.19 (2H, t), 2.59 (3H, s), 2.19-1.91 (4H, m)

[Example 7]
4-[(5-Chloropyrimidine-2-yl) oxy] -3- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} benzo [d] oxazole-2 (3H) -Manufacture of on (compound number of the present invention: E-0211):
(1) Production of 4-[(5-chloropyrimidine-2-yl) oxy] benzo [d] oxazole-2 (3H) -one (compound number: E-0001 of the present invention):
4-Hydroxybenzo [d] oxazole-2 (3H) -one 23.60 g (0.156 mol), 2,5-dichloropyrimidine 34.68 g (0.233 mol), potassium carbonate 22.64 g (0.164 mol), A mixture of 320 mL of N, N-dimethylformamide was stirred at 50 ° C. for 8 hours. After completion of the reaction, ethyl acetate, hexane and water were added to extract the aqueous layer, 3N hydrochloric acid was added to the obtained aqueous layer, extracted with ethyl acetate, and the obtained organic layer was washed with saturated brine. , Dryed with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 20.20 g (yield 49%) of the crude target product.

(2) 4-[(5-Chloropyrimidine-2-yl) oxy] -3- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} benzo [d] oxazole-2 Production of (3H) -on (compound number of the present invention: E-0211):
4-[(5-Chloropyrimidine-2-yl) oxy] benzo [d] oxazole-2 (3H) -one 11.20 g (42.5 mmol), 1- (2-bromoethyl) -3- (trifluoromethyl) ) -1H-Pyrazole 12.36 g (50.9 mmol), potassium carbonate 7.06 g (51.1 mmol), N, N-dimethylformamide 150 mL mixture was stirred at 100 ° C. for 8 hours. After completion of the reaction, ethyl acetate was added, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4: 1) to obtain 11.25 g (yield 62%) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 8.53 (2H, s), 7.44 (1H, d), 7.16 (1H, t), 7.04 (1H, 1H, d), 7.02 (1H, d), 6.85 (1H, d), 6.44 (1H, d) 4.50 (2H, t), 4.26 (2H, t)

[Example 8]
4-[(5-Chloropyrimidine-2-yl) oxy] -3- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} benzo [d] oxazole-2 (3H) -Production of thion (compound number of the present invention: E-0280):
(1) Production of N- [2,6-bis (methoxymethoxy) phenyl] formamide:
A mixture of 0.66 g (3.10 mmol) of 2,6-bis (methoxymethoxy) aniline, 0.83 g (3.93 mmol) of N-formyl saccharin and 20 mL of tetrahydrofuran was stirred at room temperature for 5 hours. After completion of the reaction, ethyl acetate was added, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 2: 1) to obtain 0.66 g (yield 88%) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 8.54 (1H, s), 7.23 (1H, t), 6.76 (2H, d), 6.02 (4H, s), 3.30 (6H, s)

(2) Production of N- [2,6-bis (methoxymethoxy) phenyl] -N- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} formamide:
N- [2,6-bis (methoxymethoxy) phenyl] formamide 0.60 g (2.49 mmol), 1- (2-bromoethyl) -3- (trifluoromethyl) -1H-pyrazole 0.85 g (3.50 mmol) ), To a mixture of 10 mL of N, N-dimethylformamide, 0.30 g of sodium hydride (7.50 mmol, converted as 60% purity) was added at room temperature, and the mixture was stirred at 40 ° C. for 6 hours. After allowing to cool at room temperature, ethyl acetate was added, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 2: 1) to obtain 0.39 g (yield 39%) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 8.02 (1H, s), 7.52 (1H, d), 7.22 (1H, t), 6.84 (2H, d), 6.44 (1H, d), 5.21 (4H, s), 4.40 (2H, t), 4.13 (2H, t), 3.44 (6H, s)

(3) Production of 2-({2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} amino) benzene-1,3-diol:
N- [2,6-bis (methoxymethoxy) phenyl] -N- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} formamide 0.35 g (0.87 mmol), 3N A mixture of 2.90 mL (8.70 mmol) of hydrochloric acid and 20 mL of methanol was heated under reflux for 3 hours. After allowing to cool at room temperature, ethyl acetate was added, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a crude target product. It was used as it was in the next step without purification.

(4) Production of 4-hydroxy-3-{2- [3- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} benzo [d] oxazole-2 (3H) -thione:
Crude 2- ({2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} amino) benzene-1,3-diol, carbon disulfide 1.64 g (21.5 mmol), water A mixture of 0.06 g (1.07 mmol) of potassium oxide and 10 mL of ethanol was stirred at 60 ° C. for 5 hours. After allowing to cool at room temperature, ethyl acetate was added, the organic layer was washed with 3N hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4: 1) to obtain 0.14 g (yield 49%, 2 steps) of the desired product. ..

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 7.88 (1H, d), 7.09 (1H, t), 6.96 (1H, d), 6.75 (1H, 1H, d), 6.63 (1H, d), 4.70 (4H, s)

(5) 4-[(5-Chloropyrimidine-2-yl) oxy] -3- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} benzo [d] oxazole-2 (3H) -Production of thione (compound number of the present invention: E-0280):
4-Hydroxy-3- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} benzo [d] oxazole-2 (3H) -thione 0.14 g (0.43 mmol), 2 A mixture of 0.08 g (0.54 mmol) of 5-dichloropyrimidine, 0.08 g (0.58 mmol) of potassium carbonate and 10 mL of N, N-dimethylformamide was stirred at 80 ° C. for 2 hours. After completion of the reaction, ethyl acetate was added, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 5: 1) to obtain 0.20 g (yield quantitative) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 8.54 (2H, s), 7.44 (1H, d), 7.29-7.26 (2H, m), 7. 12 (1H, d), 6.43 (1H, d), 4.70-4.65 (2H, m), 4.60-4.55 (2H, m)

[Example 9]
4-[(5-Chloropyrimidine-2-yl) thio] -3- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} benzo [d] oxazole-2 (3H) -Manufacture of on (compound number of the present invention: E-0321):
(1) Production of 3- (benzyloxy) -2-nitrobenzenethiol:
A mixture of 6.00 g (24.27 mmol) of 1- (benzyloxy) -3-fluoro-2-nitrobenzene, 3.79 g (48.56 mmol) of sodium sulfide and 100 mL of N, N-dimethylformamide is stirred at room temperature for 18 hours. bottom. After completion of the reaction, ethyl acetate was added, the organic layer was washed with 3N hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 5: 1) to obtain 3.10 g (yield 49%) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 7.41-7.28 (8H, m), 5.27 (2H, s)

(2) Production of 2-{[3- (benzyloxy) -2-nitrophenyl] thio} -5-chloropyrimidine:
3- (benzyloxy) -2-nitrobenzenethiol 1.70 g (6.51 mmol), 2,5-dichloropyrimidine 1.16 g (7.79 mmol), potassium carbonate 1.80 g (13.02 mmol), N, N- A mixture of 50 mL of dimethylformamide was stirred at 80 ° C. for 9 hours. After completion of the reaction, ethyl acetate was added, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 10: 1) to obtain 1.51 g (yield 62%) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 8.44 (2H, s), 7.45 (3H, t), 7.39-7.36 (5H, m), 7. 30 (1H, d), 7.20 (1H, d), 5.22 (2H, s)

(3) 2- (Benzyloxy) -6-[(5-chloropyrimidine-2-yl) thio] Production of aniline:
2-{[3- (benzyloxy) -2-nitrophenyl] thio} -5-chloropyrimidine 0.82 g (2.19 mmol), 10% Pd / C 0.20 g, tetrahydrofuran 30 mL mixture under hydrogen atmosphere (usually) Pressure), stirred at room temperature for 2 days. After completion of the reaction, the mixture was filtered through Celite, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 5: 1) to obtain 0.58 g (yield) of the desired product. 77%) Obtained.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMS δ (ppm)): 8.72 (2H, s), 7.52-7.50 (2H, m), 7.44-7.34 (3H, 3H,) m), 7.04 (1H, d), 6.97 (1H, d), 6.58 (1H, d), 5.15 (2H, s)

(4) Production of 2-amino-3-[(5-chloropyrimidine-2-yl) thio] phenol:
2- (benzyloxy) -6-[(5-chloropyrimidine-2-yl) thio] aniline 0.30 g (0.87 mmol), dichloromethane 20 mL, boron tribromide (1 mol / L dichloromethane solution) at -78 ° C. ) 4.50 mL was added, and the mixture was stirred for 1 hour while maintaining the same temperature. After completion of the reaction, water was added, the mixture was extracted with ethyl acetate, the obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 2: 1) to obtain 0.14 g (yield 63%) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMS δ (ppm)): 8.70 (2H, s), 6.82 (1H, d), 6.79 (1H, d), 6.45 (1H) , D)

(5) Production of 4-[(5-chloropyrimidine-2-yl) thio] benzo [d] oxazole-2 (3H) -one:
A mixture of 0.13 g (0.51 mmol) of 2-amino-3-[(5-chloropyrimidine-2-yl) thio] phenol, 0.10 g (0.62 mmol) of 1,1'-carbonyldiimidazole, and 40 mL of tetrahydrofuran. Was stirred at 50 ° C. for 2 hours. After completion of the reaction, ethyl acetate was added, the organic layer was washed with 3N hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4: 1) to obtain 0.13 g (yield 91%) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMS δ (ppm)): 8.77 (2H, s), 7.43 (1H, d), 7.34 (1H, d), 7.18 (1H) , T)

(6) 4-[(5-Chloropyrimidine-2-yl) thio] -3- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} benzo [d] oxazole-2 (3H) -On (compound number of the present invention: E-0321) production:
4-[(5-Chloropyrimidine-2-yl) thio] benzo [d] oxazole-2 (3H) -one 0.13 g (0.46 mmol), 1- (2-bromoethyl) -3- (trifluoromethyl) ) -1H-Pyrazole 0.17 g (0.70 mmol), potassium carbonate 0.10 g (0.72 mmol), N, N-dimethylformamide 20 mL mixture was stirred at 60 ° C. for 5 hours. After completion of the reaction, ethyl acetate was added, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 10: 1) to obtain 0.19 g (yield 93%) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMS δ (ppm)): 8.45 (2H, s), 7.38 (1H, d), 7.34 (2H, d), 7.17 (1H) , T), 6.45 (1H, d), 4.50 (4H, s)

[Example 10]
4-[(5-Chloropyrimidine-2-yl) oxy] -3- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} benzo [d] thiazole-2 (3H) -Manufacture of on (compound number of the present invention: F-0018):
(1) Production of 4-methoxy-3- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} benzo [d] thiazole-2 (3H) -one:
4-Methoxybenzo [d] thiazole-2 (3H) -one 0.33 g (1.82 mmol), 1- (2-bromoethyl) -3- (trifluoromethyl) -1H-pyrazole 0.57 g (2.35 mmol) ), 0.33 g (2.39 mmol) of potassium carbonate and 20 mL of N, N-dimethylformamide were stirred at 100 ° C. for 8 hours. After completion of the reaction, ethyl acetate was added, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 5: 1) to obtain 0.47 g (yield 75%) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 7.76 (1H, d), 7.54 (1H, d), 7.03 (1H, t), 6.86 (1H, 1H, d), 6.01 (1H, d), 5.80 (2H, t), 4.11 (2H, t), 3.86 (3H, s)

(2) Production of 4-hydroxy-3-{2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} benzo [d] thiazole-2 (3H) -one:
4-Methoxy-3-{2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} benzo [d] thiazole-2 (3H) -one 0.46 g (1.34 mmol), dichloromethane To 10 mL of the mixture, 6.70 mL of boron tribromide (1 mol / L dichloromethane solution) was added under ice-cooling, and the mixture was stirred at room temperature for 3 days. After completion of the reaction, water was added, the mixture was extracted with ethyl acetate, the obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 0.30 g (yield 68%) of the crude target product.

^{1 1} H-NMR data (300 MHz, DMSO-d ₆ / TMSδ (ppm)): 10.37 (1H, s), 7.85 (1H, d), 7.07 (1H, d), 7.01 ( 1H, t), 6.83 (1H, d), 6.65 (1H, d), 4.55 (4H, brs)

(3) 4-[(5-Chloropyrimidine-2-yl) oxy] -3- {2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} benzo [d] thiazole-2 (3H) -On (compound number of the present invention: F-0018) production:
Crude 4-hydroxy-3-{2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl} benzo [d] thiazole-2 (3H) -one 0.26 g (0.79 mmol) , 2,5-Dichloropyrimidine 0.15 g (1.01 mmol), potassium carbonate 0.15 g (1.09 mmol), N, N-dimethylformamide 5 mL mixture was stirred at 100 ° C. for 4 hours. After completion of the reaction, ethyl acetate was added, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 5: 1) to obtain 0.35 g (yield quantitative) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 8.54 (2H, s), 7.46 (1H, d), 7.35 (1H, d), 7.21 (1H, 1H, t), 7.08 (1H, d), 6.45 (1H, d), 4.48-4.45 (4H, m)

[Example 11]
7-[(5-Chloropyrimidine-2-yl) oxy] -3,3-difluoro-1- (4,4,4-trifluorobutyl) indoline-2-one (Compound number of the present invention: G-0024) )Manufacturing of:
(1) Production of 7-methoxy-1- (4,4,4-trifluorobutyl) indoline-2,3-dione:
A mixture of 1.00 g (5.64 mmol) of 7-methoxyindoline-2,3-dione, 1.09 g (7.89 mmol) of potassium carbonate, and 10 mL of N, N-dimethylformamide under ice-cooling, 1,1,1 -Trifluoro-4-iodobutane 1.61 g (6.76 mmol) was added, and the mixture was stirred at room temperature for 28 hours. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 6: 1 to 1: 1) to obtain 1.47 g (yield 91%) of the desired product. rice field.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 7.26 (1H, d), 7.19 (1H, d), 7.09 (1H, t), 4.04 (2H, t), 3.93 (3H, s), 2.27-1.12 (2H, m), 2.04-1.94 (2H, m)

(2) Production of 7-hydroxy-1- (4,4,4-trifluorobutyl) indoline-2,3-dione:
Boron tribromide (about 1 mol) in a mixture of 7-methoxy-1- (4,4,4-trifluorobutyl) indoline-2,3-dione 1.47 g (5.12 mmol) and 15 mL of dichloromethane under ice-cooling. / L dichloromethane solution) 10.20 mL (10.20 mmol) was added, and the mixture was stirred at room temperature for 22 hours. After completion of the reaction, ice water was added and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.47 g (quantitative yield) of the crude target product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 7.27 (1H, d), 7.09-6.98 (2H, m), 4.07 (2H, t), 2. 29-2.14 (2H, m), 2.10-2.00 (2H, m)

(3) 7-[(5-Chloropyrimidine-2-yl) oxy] -1- (4,4,4-trifluorobutyl) indoline-2,3-dione (Compound number of the present invention: G-089) Manufacturing of:
7-Hydroxy-1- (4,4,4-trifluorobutyl) indoline-2,3-dione 1.47 g (5.38 mmol), 2,5-dichloropyrimidine 0.96 g (6.44 mmol), potassium carbonate A mixture of 0.97 g (7.02 mmol) and 10 mL of N, N-dimethylformamide was stirred at 80 ° C. for 4.5 hours. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 9: 1 to 1: 1) to obtain 1.34 g (yield 65%) of the desired product. rice field.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 8.55 (2H, s), 7.59 (1H, d), 7.40 (1H, d), 7.18 (1H, 1H, t), 3.88 (2H, t), 2.20-2.04 (2H, m), 1.90-1.80 (2H, m)

(4) 7-[(5-Chloropyrimidine-2-yl) oxy] -3,3-difluoro-1- (4,4,4-trifluorobutyl) indoline-2-one (Compound number of the present invention: Manufacture of G-0024):
7-[(5-Chloropyrimidine-2-yl) oxy] -1- (4,4,4-trifluorobutyl) Indoline-2,3-dione 0.27 g (0.70 mmol) in a mixture of 10 mL of dichloromethane , 0.36 g (2.23 mmol) of (dichloromethane) sulfatrifluoride was added under ice-cooling, and the mixture was stirred at room temperature for 48 hours. After completion of the reaction, ice water was added and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 20: 1 to 3: 2) to obtain 0.29 g (yield quantitative) of the desired product. rice field.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 8.55 (2H, s), 7.50 (1H, d), 7.30-7.18 (2H, m), 3. 84 (2H, t), 2.18-2.02 (2H, m), 1.89-1.78 (2H, m)

[Example 12]
4-[(5-Chloropyrimidine-2-yl) oxy] -1-methyl-3- (4,4,4-trifluorobutyl) -1,3-dihydro-2H-benzo [d] imidazole-2- Manufacture of ON (compound number of the present invention: H-0003):
(1) Production of 4-Methoxy-1-methyl-3- (4,4,4-trifluorobutyl) -1,3-dihydro-2H-benzo [d] imidazole-2-one:
4-Methoxy-1-methyl-1,3-dihydro-2H-benzo [d] imidazol-2-one 0.60 g (3.37 mmol), 1,1,1-trifluoro-4-iodobutane 1.12 g ( A mixture of 4.71 mmol), 0.70 g (5.07 mmol) of potassium carbonate and 10 mL of N, N-dimethylformamide was stirred at 70 ° C. for 4 hours. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and used as it was in the next step without purification.

(2) Production of 4-hydroxy-1-methyl-3- (4,4,4-trifluorobutyl) -1,3-dihydro-2H-benzo [d] imidazole-2-one:
Crude 4-methoxy-1-methyl-3- (4,4,4-trifluorobutyl) -1,3-dihydro-2H-benzo [d] imidazol-2-one, dichloromethane 10 mL mixture, ice-cooled Below, 17.0 mL of boron tribromide (1 mol / L dichloromethane solution) was added, and the mixture was stirred at room temperature for 20 hours. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 3: 1) to obtain 0.84 g (yield 91%, 2 steps) of the desired product. ..

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 8.11 (1H, d), 7.02 (1H, t), 6.83 (1H, d), 3.89 (3H, s), 3.87 (2H, t), 2.14-2.05 (2H, m), 1.91-1.83 (2H, m)

(3) 4-[(5-Chloropyrimidine-2-yl) oxy] -1-methyl-3- (4,4,4-trifluorobutyl) -1,3-dihydro-2H-benzo [d] imidazole Production of -2-one (compound number of the present invention: H-0003):
4-Hydroxy-1-methyl-3- (4,4,4-trifluorobutyl) -1,3-dihydro-2H-benzo [d] imidazol-2-one 0.21 g (0.77 mmol), 2, A mixture of 0.14 g (0.94 mmol) of 5-dichloropyrimidine, 0.13 (0.94 mmol) of potassium carbonate and 10 mL of N, N-dimethylformamide was stirred at 80 ° C. for 8 hours. After completion of the reaction, ethyl acetate was added, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 5: 1) to obtain 0.29 g (yield 98%) of the desired product.

^{1 1} H-NMR data (300 MHz, CDCl ₃ / TMSδ (ppm)): 8.52 (2H, s), 7.14 (1H, t), 6.91 (1H, d), 6.88 (1H, d), 3.95 (2H, t), 2.14-2.05 (2H, m), 1.91-1.83 (2H, m)

The physical characteristic values of the compound [I] of the present invention synthesized according to the above-mentioned examples, including the values in the above-mentioned examples, are shown in Tables 38 to 54 below. The compound numbers and symbols in the table have the same meanings as described above.

Next, a pharmaceutical example of the herbicide of the present invention using the condensed heterocyclic derivative of the present invention or an agriculturally acceptable salt thereof produced as described above will be specifically described. However, the types and blending ratios of compounds and additives are not limited to this and can be changed in a wide range. Further, in the following description, "part" means a mass part.

[Preparation Example 1] Emulsion 10 parts of each compound shown in Tables 1 to 37 and 38 to 54 parts of cyclohexanone 30 parts of polyoxyethylene alkylaryl ether 11 parts of calcium alkylbenzene sulfonate 4 parts of methylnaphthalene 45 parts or more are uniformly dissolved. To make an emulsion.

[Preparation Example 2] Wettable Powder 10 parts of each compound shown in Tables 1 to 37 and Table 38 to Table 54 Naphthalene Sulfonic Acid Formarin Condensate Sodium Salt 0.5 Part Polyoxyethylene Alkylaryl Ether 0.5 Part Silica Soil 24 65 parts or more of clay was uniformly mixed and pulverized to obtain a wettable powder.

[Pharmaceutical Example 3] Powders 2 parts of each compound shown in Tables 1 to 37 and Tables 38 to 54 5 parts of diatomaceous earth 93 parts of clay The above are uniformly mixed and pulverized to form a powder.

[Preparation Example 4] Granules 5 parts of each compound shown in Tables 1 to 37 and 38 to 54 parts Sodium salt of lauryl alcohol sulfate 2 parts Sodium lignin sulfonate 5 parts Carboxymethyl cellulose 2 parts Clay 86 parts or more is uniform Was mixed and crushed. An amount equivalent to 20 parts of water was added to this mixture, kneaded, processed into granules of 14 to 32 mesh using an extrusion type granulator, and then dried to obtain granules.

[Formulation Example 5] Flowable Agents 20 parts of each compound shown in Tables 1 to 37 and Tables 38 to 54 Polyoxyethylene styrenated phenyl ether sulfate 4 parts Ethylene glycol 7 parts Silicone AF-118N (manufactured by Asahi Kasei Kogyo Co., Ltd.) ) 0.02 parts Water 68.98 parts or more was mixed with a high-speed stirrer for 30 minutes and then crushed with a wet crusher to obtain a flowable agent.

[Pharmaceutical Example 6] Granule wettable powder 10 parts of each compound shown in Tables 1 to 37 and Tables 38 to 54 5 parts of sodium lignin sulfonate 5 parts of polyoxyethylene alkylaryl ether 1 part of sodium polycarboxylate 3 parts of white carbon 5 Part 1 part of pregelatinized starch 1 part of calcium carbonate 65 parts of water 10 parts or more of water was mixed and kneaded and granulated. The obtained granules were dried in a fluidized bed dryer to obtain a granule wettable powder.

Next, the herbicidal activity of the herbicide of the present invention using the pharmaceutical product containing the fused heterocyclic derivative of the present invention or an agriculturally acceptable salt thereof produced as described above as an active ingredient will be specifically described.

[Test Example 1] Test for confirming herbicidal activity against barnyard grass in foliage treatment:
Field soil was filled in a plastic pot of about 340 cm and ³ volumes, and barnyard grass seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 1000 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

The compounds that had a herbicidal effect on barnyard grass in the foliage treatment were compounds A-0004, A-0015, A-0041, B-0008, B-0152, B-0153, B-0154, B-0156, B. -0157, B-0158, B-0162, B-0221, B-0245, B-0247, B-0273, B-0275, B-0301, B-0303, B-034, B-0305, B-0307 , B-0309, B-0310, B-0311, B-0314, B-0325, B-0327, B-0328, B-0333, B-0334, B-0338, B-0342, B-0350, B -0359, B-0368, B-0369, B-0370, B-0372, B-0376, B-0377, B-0384, B-0387, B-0389, B-0399, B-0403, B-0405 , B-0409, B-0441, B-0448, B-0462, B-0466, B-0468, B-0469, B-0493, B-0499, B-0514, B-0543, B-0544, B -0556, B-0561, B-0563, B-0565, B-0566, B-0573, B-0574, B-0575, B-0576, B-0577, B-0578, B-0579, B-0580 , B-0581, B-0585, B-0586, B-0588, B-0590, B-0592, B-0593, C-0002, C-0012, C-0018, C-0033, E-0006, E -0007, E-0009, E-0014, E-0015, E-0031, E-0032, E-0040, E-0043, E-0045, E-0051, E-0052, E-0059, E-0061 , E-0105, E-0106, E-0108, E-0109, E-0111, E-0124, E-0172, E-0173, E-0174, E-0181, E-0211, E-0212, E -0219, E-0220, E-0230, E-0231, E-0232, E-0238, E-0258, E-0280, E-0403, E-0408, E-0418, E-0420, E-0422 , F-0002, F-0018, F-0020, F-0021, F-0084, F-0088, F-0102, F-0103, F-0107, G-0024, G-0033, G-0051, G -0056, G-0070, G-0090, H-0003.

[Test Example 2] Test for confirming herbicidal activity against Festuca perensis in foliage treatment:
The field soil was filled in a plastic pot of about 340 cm and ³ volumes, and the seeds of Festuca perennial were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 1000 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

The compounds that had a herbicidal effect on Festuca perennial in the foliage treatment were Compounds A-0032, B-0008, B-00908, B-0152, B-0153, B-0154, B-0156, B-0158, B. -0162, B-0221, B-0245, B-0247, B-0273, B-0276, B-0301, B-0303, B-0304, B-0309, B-0310, B-0311, B-0314 , B-0325, B-0327, B-0328, B-0333, B-0334, B-0338, B-0342, B-0359, B-0368, B-0369, B-0370, B-0372, B -0376, B-0377, B-0384, B-0387, B-0389, B-0399, B-0403, B-0405, B-0409, B-0448, B-0461, B-0462, B-0466 , B-0468, B-0469, B-0493, B-0499, B-0514, B-0537, B-0543, B-0544, B-0556, B-0561, B-0563, B-0565, B -0573, B-0574, B-0576, B-0577, B-0578, B-0579, B-0580, B-0581, B-0586, B-0588, B-0590, B-0592, B-0593 , C-0002, E-0007, C-0012, E-0015, C-0018, E-0031, E-0032, C-0033, E-0051, E-0061, E-0105, E-0106, E -0111, E-0173, E-0174, E-0181, E-0182, E-0196, E-0211, E-0219, E-0231, E-0238, E-0280, E-0403, E-0419 , E-0420, E-0422, F-0002, F-0018, F-0020, F-0021, F-0084, F-0102, F-0103, F-0107, G-0024, G-0051, G -0056, G-0063, G-0070.

[Test Example 3] Herbicidal activity confirmation test for velvetleaf in foliage treatment:
Field soil was filled in a plastic pot of about 340 cm and ³ volumes, and velvetleaf seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 1000 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

The compounds that had a herbicidal effect on velvetleaf by foliar spraying were compounds A-0004, A-0007, A-0015, A-0032, A-0036, A-0041, A-0065, A-0066, B. -0008, B-0998, B-0152, B-0153, B-0154, B-0156, B-0157, B-0158, B-0160, B-0162, B-0217, B-0221, B-0245 , B-0247, B-0266, B-0273, B-0275, B-0276, B-0301, B-0303, B-0304, B-0305, B-0307, B-0309, B-0310, B -0311, B-0314, B-0316, B-0325, B-0327, B-0328, B-0333, B-0334, B-0338, B-0342, B-0350, B-0359, B-0368 , B-0369, B-0370, B-0372, B-0374, B-0376, B-0377, B-0384, B-0387, B-0389, B-0399, B-0403, B-0405, B -0409, B-0434, B-0438, B-0448, B-0451, B-0461, B-0462, B-0466, B-0468, B-0469, B-0493, B-0499, B-0500 , B-0514, B-0543, B-0544, B-0556, B-0557, B-0561, B-0562, B-0563, B-0564, B-0565, B-0566, B-0572, B -0573, B-0574, B-0575, B-0576, B-0577, B-0578, B-0579, B-0580, B-0581, B-0582, B-0583, B-0584, B-0585 , B-0586, B-0587, B-0588, B-0589, B-0590, B-0591, B-0592, B-0593, B-0594, B-0595, C-0002, C-0012, C -0018, C-0033, E-0006, E-0007, E-0009, E-0014, E-0015, E-0020, E-0030, E-0031, E-0032, E-0039, E-0040 , E-0042, E-0043, E-0045, E-0046, E-0048, E-0050, E-0051, E-0052, E-0058, E-0059, E-0074, E-0104, E -0105, E-0106, E-0108, E-0109, E-0110, E-01 24, E-0125, E-0126, E-0127, E-0128, E-0147, E-0172, E-0173, E-0174, E-0175, E-0177, E-0181, E-0182, E-0183, E-0186, E-0189, E-0192, E-0196, E-0197, E-0206, E-0211, E-0219, E-0220, E-0221, E-0222, E- 0226, E-0230, E-0231, E-0232, E-0233, E-0238, E-0257, E-0258, E-0272, E-0275, E-0280, E-0321, E-0403, E-0408, E-0409, E-0418, E-0419, E-0420, E-0422, F-0002, F-0018, F-0020, F-0021, F-0084, F-0083, F- 0086, F-0088, F-0102, F-0103, F-0105, F-0107, G-0024, G-0033, G-0051, G-0056, G-0058, G-0063, G-0070, It was G-0144 and H-0002.

[Test Example 4] Test for confirming herbicidal activity against Amaranthus retroflexa in foliage treatment:
The field soil was filled in a plastic pot of about 340 cm and ³ volumes, and Amaranthus retroflexa seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 1000 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

The compounds that had a herbicidal effect on Amaranthus retroflexa in the foliage treatment were compounds A-0002, A-0004, A-0007, A-0015, A-0032, A-0036, A-0041, A-0065, A. -0066, B-0008, B-0598, B-0152, B-0153, B-0154, B-0156, B-0157, B-0158, B-0160, B-0162, B-0217, B-0221 , B-0245, B-0247, B-0266, B-0273, B-0275, B-0276, B-0301, B-0303, B-0304, B-0305, B-0307, B-0309, B -0310, B-0311, B-0314, B-0316, B-0325, B-0327, B-0328, B-0333, B-0334, B-0338, B-0342, B-0350, B-0359 , B-0362, B-0368, B-0369, B-0370, B-0372, B-0373, B-0374, B-0376, B-0377, B-0384, B-0387, B-0389, B -0399, B-0403, B-0405, B-0409, B-0434, B-0438, B-0441, B-0448, B-0451, B-0461, B-0462, B-0466, B-0468 , B-0469, B-0492, B-0493, B-0499, B-0500, B-0514, B-0537, B-0543, B-0544, B-0556, B-0557, B-0560, B -0561, B-0562, B-0563, B-0564, B-0565, B-0566, B-0572, B-0573, B-0574, B-0575, B-0576, B-0577, B-0578 , B-0579, B-0580, B-0581, B-0582, B-0583, B-0584, B-0585, B-0586, B-0587, B-0588, B-0589, B-0590, B -0591, B-0592, B-0593, B-0594, B-0595, C-0002, C-0012, C-0018, C-0033, D-0002, E-0006, E-0007, E-0009 , E-0014, E-0015, E-0020, E-0029, E-0030, E-0031, E-0032, E-0039, E-0040, E-0042, E-0043, E-0045, E -0046, E-0048, E-0050, E-0051, E-0052, E -0053, E-0058, E-0059, E-0061, E-0104, E-0105, E-0106, E-0108, E-0109, E-0110, E-0124, E-0125, E-0126 , E-0127, E-0128, E-0147, E-0171, E-0172, E-0173, E-0174, E-0175, E-0177, E-0181, E-0182, E-0183, E -0186, E-0192, E-0196, E-0197, E-0206, E-0211, E-0212, E-0214, E-0219, E-0220, E-0221, E-0222, E-0226 , E-0228, E-0229, E-0230, E-0231, E-0232, E-0233, E-0236, E-0238, E-0243, E-0247, E-0257, E-0258, E -0268, E-0272, E-0275, E-0280, E-0305, E-0313, E-0315, E-0321, E-0403, E-0406, E-0408, E-0409, E-0418 , E-0419, E-0420, E-0421, E-0422, F-0002, F-0018, F-0019, F-0020, F-0021, F-0084, F-0083, F-0086, F -0087, F-0088, F-0081, F-0102, F-0103, F-0104, F-0105, F-0107, G-0024, G-0033, G-0034, G-0051, G-0056 , G-0058, G-0063, G-0065, G-0070, G-0071, G-0089, G-0090, G-0144, G-0148, H-0002.

[Test Example 5] Test for confirming herbicidal activity against barnyard grass in soil treatment:
Field soil was filled in a plastic pot of about 340 cm and ³ volumes, and barnyard grass seeds were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 1000 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

Compounds that had a herbicidal effect on barnyard grass in soil treatment were compounds A-0001, A-0004, A-0015, A-0032, A-0036, A-0041, A-0065, B-0008, B. -0898, B-0152, B-0153, B-0154, B-0156, B-0157, B-0158, B-0160, B-0162, B-0221, B-0245, B-0247, B-0266 , B-0273, B-0275, B-0276, B-0301, B-0303, B-0304, B-0305, B-0307, B-0309, B-0310, B-0311, B-0314, B -0325, B-0327, B-0328, B-0333, B-0334, B-0338, B-0342, B-0350, B-0359, B-0368, B-0369, B-0370, B-0372 , B-0376, B-0377, B-0384, B-0387, B-0389, B-0399, B-0403, B-0405, B-0409, B-0438, B-0441, B-0448, B -0461, B-0462, B-0466, B-0468, B-0469, B-0493, B-0499, B-0514, B-0537, B-0543, B-0544, B-0556, B-0561 , B-0563, B-0565, B-0566, B-0572, B-0573, B-0574, B-0576, B-0577, B-0578, B-0579, B-0580, B-0581, B -0582, B-0585, B-0586, B-0588, B-0589, B-0590, B-0591, B-0592, B-0593, B-0594, C-0002, C-0012, C-0018 , C-0033, E-0006, E-0007, E-0009, E-0014, E-0015, E-0030, E-0031, E-0032, E-0040, E-0043, E-0045, E -0048, E-0050, E-0051, E-0052, E-0053, E-0058, E-0059, E-0061, E-0105, E-0106, E-0108, E-0109, E-0111 , E-0124, E-0125, E-0126, E-0127, E-0128, E-0171, E-0172, E-0173, E-0174, E-0175, E-0177, E-0181, E 0182, E-0192, E-0194, E-0211, E-0212, E-0 219, E-0220, E-0221, E-0230, E-0231, E-0232, E-0238, E-0257, E-0258, E-0272, E-0275, E-0280, E-0313, E-0315, E-0403, E-0408, E-0409, E-0418, E-0419, E-0420, E-0421, E-0422, F-0002, F-0018, F-0020, F- 0021, F-0084, F-805, F-0088, F-0102, F-0103, F-0105, F-0107, G-0024, G-0033, G-0051, G-0056, G-0063, They were G-0070, G-0090, G-0148, H-0002, and H-0003.

[Test Example 6] Test for confirming herbicidal activity against Festuca perensis in soil treatment:
The field soil was filled in a plastic pot of about 340 cm and ³ volumes, and the seeds of Festuca perennial were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 1000 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

Compounds that had a herbicidal effect on Festuca perennial in soil treatment were compounds A-0004, A-0015, A-0032, A-0036, A-0041, B-0008, B-00908, B-0152, B. -0153, B-0154, B-0156, B-0157, B-0158, B-0162, B-0221, B-0245, B-0247, B-0266, B-0273, B-0275, B-0276 , B-0301, B-0303, B-0304, B-0305, B-0307, B-0309, B-0310, B-0311, B-0314, B-0325, B-0327, B-0328, B -0333, B-0334, B-0338, B-0342, B-0350, B-0359, B-0368, B-0369, B-0370, B-0372, B-0374, B-0376, B-0377 , B-0384, B-0387, B-0389, B-0399, B-0403, B-0405, B-0409, B-0438, B-0448, B-0461, B-0462, B-0466, B -0468, B-0469, B-0493, B-0499, B-0514, B-0537, B-0543, B-0544, B-0556, B-0561, B-0563, B-0564, B-0565 , B-0566, B-0572, B-0573, B-0574, B-0576, B-0577, B-0578, B-0579, B-0580, B-0581, B-0582, B-0583, B -0584, B-0585, B-0586, B-0588, B-0589, B-0590, B-0591, B-0592, B-0593, B-0594, B-0595, C-0002, C-0012 , C-0018, C-0033, E-0006, E-0007, E-0009, E-0014, E-0015, E-0030, E-0031, E-0032, E-0040, E-0043, E -0045, E-0048, E-0050, E-0051, E-0052, E-0053, E-0058, E-0059, E-0061, E-0105, E-0106, E-0109, E-0111 , E-0124, E-0127, E-0128, E-0171, E-0172, E-0173, E-0174, E-0175, E-0177, E-0181, E-0182, E-0183, E -0192, E-0194, E-0211, E-0212, E-0219, E- 0220, E-0221, E-0230, E-0231, E-0232, E-0238, E-0243, E-0257, E-0258, E-0280, E-0313, E-0315, E-0321, E-0403, E-0408, E-0409, E-0418, E-0419, E-0420, E-0421, E-0422, F-0002, F-0018, F-0019, F-0020, F- 0021, F-0084, F-805, F-0088, F-0102, F-0103, F-0104, F-0107, G-0024, G-0033, G-0051, G-0056, G-0063, They were G-0070, G-0090, and G-0148.

[Test Example 7] Confirmation test of herbicidal activity against velvetleaf in soil treatment:
Field soil was filled in a plastic pot of about 340 cm and ³ volumes, and velvetleaf seeds were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 1000 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

Compounds that had a herbicidal effect on velvetleaf in soil treatment were compounds A-0036, A-0041, B-0008, B-00908, B-0152, B-0153, B-0158, B-0221, B. -0245, B-0247, B-0266, B-0273, B-0275, B-0276, B-0301, B-0303, B-0304, B-0309, B-0310, B-0311, B-0314 , B-0325, B-0327, B-0328, B-0333, B-0334, B-0338, B-0342, B-0350, B-0359, B-0368, B-0369, B-0370, B -0376, B-0377, B-0384, B-0387, B-0389, B-0403, B-0409, B-0448, B-0461, B-0462, B-0468, B-0469, B-0493 , B-0499, B-0514, B-0537, B-0543, B-0544, B-0556, B-0561, B-0563, B-0565, B-0566, B-0572, B-0573, B -0574, B-0576, B-0577, B-0578, B-0579, B-0580, B-0585, B-0586, B-0588, B-0591, C-0002, C-0012, C-0018 , C-0033, E-0006, E-0007, E-0009, E-0014, E-0015, E-0030, E-0031, E-0032, E-0039, E-0040, E-0043, E -0045, E-0048, E-0050, E-0051, E-0052, E-0053, E-0059, E-0061, E-0105, E-0106, E-0108, E-0109, E-0111 , E-0124, E-0171, E-0172, E-0174, E-0181, E-0183, E-0211, E-0212, E-0219, E-0220, E-0221, E-0230, E -0231, E-0238, E-0243, E-0257, E-0258, E-0272, E-0275, E-0280, E-0321, E-0403, E-0408, E-0409, E-0418 , E-0420, E-0421, E-0422, F-0002, F-0018, F-0020, F-0021, F-0084, F-0102, F-0103, F-0107, G-0024, G. -0033, G-0051, G-0056, G-0063, G-0070, H-00 It was 02.

[Test Example 8] Test for confirming herbicidal activity against Amaranthus retroflexus in soil treatment:
Field soil was filled in a plastic pot of about 340 cm and ³ volumes, and Amaranthus retroflexa seeds were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 1000 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

Compounds that had a herbicidal effect on Amaranthus retroflexa in soil treatment were compounds A-0004, A-0015, A-0032, A-0036, A-0041, A-0065, B-0008, B-00908, B. -0152, B-0153, B-0154, B-0156, B-0157, B-0158, B-0160, B-0162, B-0217, B-0221, B-0245, B-0247, B-0266 , B-0273, B-0275, B-0276, B-0301, B-0303, B-0304, B-0305, B-0307, B-0309, B-0310, B-0311, B-0314, B -0316, B-0325, B-0327, B-0328, B-0333, B-0334, B-0338, B-0342, B-0350, B-0359, B-0362, B-0368, B-0369 , B-0370, B-0372, B-0374, B-0376, B-0377, B-0384, B-0387, B-0389, B-0399, B-0403, B-0405, B-0409, B -0438, B-0441, B-0448, B-0451, B-0461, B-0462, B-0466, B-0468, B-0469, B-0492, B-0493, B-0499, B-0514 , B-0537, B-0543, B-0544, B-0556, B-0561, B-0562, B-0563, B-0564, B-0565, B-0566, B-0572, B-0573, B -0574, B-0575, B-0576, B-0577, B-0578, B-0579, B-0580, B-0581, B-0582, B-0583, B-0584, B-0585, B-0586 , B-0587, B-0588, B-0589, B-0590, B-0591, B-0592, B-0593, B-0594, B-0595, C-0002, C-0012, C-0018, C -0033, E-0006, E-0007, E-0009, E-0014, E-0015, E-0020, E-0029, E-0030, E-0031, E-0032, E-0039, E-0040 , E-0043, E-0045, E-0046, E-0048, E-0050, E-0051, E-0052, E-0053, E-0059, E-0061, E-0104, E-0105, E -0106, E-0108, E-0109, E-0111, E-0124, E -0125, E-0126, E-0127, E-0128, E-0147, E-0171, E-0172, E-0173, E-0174, E-0175, E-0177, E-0181, E-0182 , E-0183, E-0189, E-0192, E-0194, E-0196, E-0206, E-0211, E-0212, E-0214, E-0219, E-0220, E-0221, E -0222, E-0226, E-0228, E-0229, E-0230, E-0231, E-0232, E-0233, E-0236, E-0238, E-0243, E-0257, E-0258 , E-0272, E-0275, E-0280, E-0305, E-0313, E-0315, E-0321, E-0403, E-0406, E-0408, E-0409, E-0418, E -0419, E-0420, E-0421, E-0422, F-0002, F-0018, F-0019, F-0020, F-0021, F-0084, F-0087, F-0086, F-0087 , F-0088, F-0008, F-0102, F-0103, F-0104, F-0105, F-0106, F-0107, G-0024, G-0033, G-0034, G-0051, G -0056, G-0058, G-0063, G-0065, G-0070, G-0089, G-0090, G-0144, G-0148, H-0002, H-0003.

[Test Example 9] Test for confirming herbicidal activity against barnyard grass in foliage treatment:
Field soil was filled in a plastic pot of about 3020 cm ³ volumes, and barnyard grass seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 250 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

The compound that had a herbicidal effect on barnyard grass in the foliage treatment was compound B-0536.

[Test Example 10] Herbicidal activity confirmation test for velvetleaf in foliage treatment:
The field soil was filled in a plastic pot of about 3020 cm ³ volumes, and velvetleaf seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 250 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

The compound that had a herbicidal effect on velvetleaf in the foliage treatment was compound B-0536.

[Test Example 11] Test for confirming herbicidal activity against barnyard grass in soil treatment:
Field soil was filled in a plastic pot of about 3020 cm ³ volumes, and barnyard grass seeds were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 1000 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

The compound that had a herbicidal effect on barnyard grass in soil treatment was compound B-0536.

[Test Example 12] Confirmation test of herbicidal activity against velvetleaf in soil treatment:
Field soil was filled in a plastic pot of about 3020 cm ³ volumes, and velvetleaf seeds were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 1000 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

The compound that had a herbicidal effect on velvetleaf in soil treatment was compound B-0536.

[Test Example 13] Test for confirming herbicidal activity against barnyard grass in a hydroponic test:
Spread cotton in a 60 ml plastic cup, dilute 8 ml of the wettable powder adjusted according to Pharmaceutical Example 2 with water so that the concentration of the test compound becomes 200 ppm, and then pour 8 ml of it, and then pour 8 ml of Inubier seeds on the cotton surface. Was sown. After closing the lid, the cultivation was continued under the conditions of 12 hours light period / 12 hours dark period and about 20 ° C. by irradiation with a fluorescent lamp, and the herbicidal effect was confirmed about 7 days after the treatment.

In the hydroponic test, the compounds that had a herbicidal effect on barnyard grass were compounds A-0067, B-0342, B-0560, B-0563, D-0010, D-0011, D-0020, E-0001, E-0052, E-0074, E-0906, E-0106, E-0108, E-0109, E-0111, E-0117, E-0207, E-0213, E-0223, E-0240, E- They were 0249, E-0257, E-0260, E-0276, E-0403, E-0420, and G-0051.

[Test Example 14] Test for confirming herbicidal activity against Festuca perensis in a hydroponic test:
Spread cotton in a 60 ml plastic cup, dilute 8 ml of the wettable powder adjusted according to Pharmaceutical Example 2 with water so that the concentration of the test compound becomes 200 ppm, and then pour 8 ml of it, and then pour 8 ml of rat seeds on the cotton surface. Was sown. After closing the lid, the cultivation was continued under the conditions of 12 hours light period / 12 hours dark period and about 20 ° C. by irradiation with a fluorescent lamp, and the herbicidal effect was confirmed about 7 days after the treatment.

In the hydroponic test, the compounds that had a herbicidal effect on Festuca perennial were compounds A-0067, B-0342, B-0560, B-0563, D-0010, D-0011, D-0020, E-0001, E-0052, E-0074, E-0906, E-0106, E-0108, E-0109, E-0111, E-0170, E-0189, E-0197, E-0207, E-0213, E- They were 0223, E-0240, E-0249, E-0257, E-0276, E-0403, E-0420, and G-0051.

[Test Example 15] Confirmation test of herbicidal activity against lettuce in hydroponic test:
Spread cotton in a 60 ml plastic cup, dilute 8 ml of the wettable powder adjusted according to Pharmaceutical Example 2 with water so that the concentration of the test compound becomes 200 ppm, and then pour 8 ml of lettuce seeds on the cotton surface. Was sown. After closing the lid, the cultivation was continued under the conditions of 12 hours light period / 12 hours dark period and about 20 ° C. by irradiation with a fluorescent lamp, and the herbicidal effect was confirmed about 7 days after the treatment.

In the hydroponic test, the compounds that had a herbicidal effect on lettuce were compounds A-0067, B-0342, B-0563, D-0010, D-0011, D-0020, E-0001, E-0052, E-0074, E-0906, E-0106, E-0108, E-0109, E-0111, E-0207, E-0240, E-0249, E-0257, E-0276, E-0403, E- It was 0420 and G-0051.

[Test Example 16] Test for confirming herbicidal activity against Amaranthus retroflexus in a hydroponic test:
Spread cotton in a 60 ml plastic cup, dilute 8 ml of the wettable powder adjusted according to Pharmaceutical Example 2 with water so that the concentration of the test compound becomes 200 ppm, and then pour 8 ml of it, and then pour 8 ml of Amaranthus retroflexa seeds on the cotton surface. Was sown. After closing the lid, the cultivation was continued under the conditions of 12 hours light period / 12 hours dark period and about 20 ° C. by irradiation with a fluorescent lamp, and the herbicidal effect was confirmed about 7 days after the treatment.

In the hydroponic test, the compounds that had a herbicidal effect on Amaranthus retroflexa were compounds A-0067, B-0342, B-0560, B-0563, D-0010, D-0011, D-0020, D-0021, E-0001, E-0052, E-0074, E-0906, E-0106, E-0108, E-0109, E-0111, E-0117, E-0147, E-0189, E-0197, E- They were 0207, E-0213, E-0223, E-0240, E-0249, E-0257, E-0260, E-0266, E-0276, E-0403, E-0420, and G-0051.

[Test Example 17] Test for confirming herbicidal activity against dog firefly in a hydroponic test:
Spread cotton in a 60 ml plastic cup, dilute 8 ml of the wettable powder adjusted according to Pharmaceutical Example 2 with water so that the concentration of the test compound becomes 200 ppm, and then pour 8 ml of it, and then inu firefly seeds on the cotton surface. Was sown. After closing the lid, the cultivation was continued under the conditions of 12 hours light period / 12 hours dark period and about 20 ° C. by irradiation with a fluorescent lamp, and the herbicidal effect was confirmed about 7 days after the treatment.

In the hydroponic test, the compounds that had a herbicidal effect on dog firefly were compounds A-0067, B-0342, B-0563, D-0010, D-0011, D-0020, E-0001, E-0052, E-0074, E-0906, E-0106, E-0108, E-0109, E-0111, E-0117, E-0189, E-0207, E-0213, E-0223, E-0240, E- They were 0249, E-0257, E-0260, E-0266, E-0276, E-0403, E-0420, and G-0051.

[Test Example 18] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is a chlorine atom. Test for confirming herbicidal activity against barnyard grass in
Field soil was filled in a plastic pot of about 340 cm and ³ volumes, and barnyard grass seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to the compounds B-0153, B-0154, B-0156 and B-0462 in the herbicidal effect on barnyard grass was compound B-0245.

[Test Example 19] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is a chlorine atom. Weeding activity confirmation test for rat wheat in
The field soil was filled in a plastic pot of about 340 cm and ³ volumes, and the seeds of Festuca perennial were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to the compounds B-0152, B-0153, B-0154, B-0156 and B-0462 in the herbicidal effect on the rat wheat was compound B-0245.

[Test Example 20] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is a chlorine atom. Weeding activity confirmation test for velvetleaf in
Field soil was filled in a plastic pot of about 340 cm and ³ volumes, and velvetleaf seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to the compounds B-0154, B-0156 and B-0462 in the herbicidal effect on velvetleaf was compound B-0245.

[Test Example 21] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is a chlorine atom. Weeding activity confirmation test for Amaranthus retroflexus in
The field soil was filled in a plastic pot of about 340 cm and ³ volumes, and Amaranthus retroflexa seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to the compounds B-0154 and B-0156 in the herbicidal effect on Amaranthus retroflexa was compound B-0245.

[Test Example 22] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , soil treatment of a compound in which R3 is a chlorine atom Test for confirming herbicidal activity against barnyard grass in
Field soil was filled in a plastic pot of about 340 cm and ³ volumes, and barnyard grass seeds were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In soil treatment, the compound superior to compounds B-0152, B-0153, B-0154, B-0156 and B-0462 in herbicidal effect on barnyard grass was compound B-0245.

[Test Example 23] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , soil treatment of a compound in which R3 is a chlorine atom. Weeding activity confirmation test for rat wheat in
The field soil was filled in a plastic pot of about 340 cm and ³ volumes, and the seeds of Festuca perennial were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In soil treatment, the compound superior to compounds B-0152, B-0153, B-0154, B-0156 and B-0462 in herbicidal effect on Festuca perennial was compound B-0245.

[Test Example 24] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , soil treatment of a compound in which R3 is a chlorine atom Weeding activity confirmation test for velvetleaf in
Field soil was filled in a plastic pot of about 340 cm and ³ volumes, and velvetleaf seeds were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In soil treatment, the compound superior to compounds B-0153, B-0154, B-0156 and B-0462 in herbicidal effect on velvetleaf was compound B-0245.

[Test Example 25] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , soil treatment of a compound in which R3 is a chlorine atom Weeding activity confirmation test for Amaranthus retroflexus in
Field soil was filled in a plastic pot of about 340 cm and ³ volumes, and Amaranthus retroflexa seeds were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In soil treatment, the compound superior to compounds B-0154, B-0156 and B-0462 in herbicidal effect on Amaranthus retroflexa was compound B-0245.

[Test Example 26] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is an iodine atom. Weeding activity confirmation test for rat wheat in
The field soil was filled in a plastic pot of about 340 cm and ³ volumes, and the seeds of Festuca perennial were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to the compound B-034 in the herbicidal effect on the rat wheat was the compound B-0309.

[Test Example 27] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Confirmation test of herbicidal activity against barnyard grass in foliage treatment:
Field soil was filled in a plastic pot of about 340 cm and ³ volumes, and barnyard grass seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to the compounds B-0328 and B-0469 in the herbicidal effect on barnyardgrass was compound B-0333.

[Test Example 28] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Confirmation test of herbicidal activity against Festuca perensis in foliage treatment:
The field soil was filled in a plastic pot of about 340 cm and ³ volumes, and the seeds of Festuca perennial were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to the compounds B-0328 and B-0469 in the herbicidal effect on the rat wheat was the compound B-0544.

[Test Example 29] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Confirmation test of herbicidal activity against velvetleaf in foliage treatment:
Field soil was filled in a plastic pot of about 340 cm and ³ volumes, and velvetleaf seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

The compounds superior to compound B-0328 in the herbicidal effect on velvetleaf in the foliage treatment were compounds B-0333 and B-0544.

[Test Example 30] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Confirmation test of herbicidal activity against Amaranthus retroflexa in foliage treatment:
The field soil was filled in a plastic pot of about 340 cm and ³ volumes, and Amaranthus retroflexa seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

The compounds superior to compound B-0328 in the herbicidal effect on Amaranthus retroflexa in the foliage treatment were compounds B-0333 and B-0544.

[Test Example 31] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Confirmation test of herbicidal activity against barnyard grass in soil treatment:
Field soil was filled in a plastic pot of about 340 cm and ³ volumes, and barnyard grass seeds were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In soil treatment, the compound superior to compounds B-0328 and B-0469 in the herbicidal effect on barnyard grass was compound B-0544.

[Test Example 32] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Confirmation test of herbicidal activity against Festuca perensis in soil treatment:
Field soil was filled in a plastic pot of about 340 cm and ³ volumes, and Festuca perennial seeds were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the soil treatment, the compounds superior to the compounds B-0328 and B-0469 in the herbicidal effect on the rat wheat were the compounds B-0333 and B-0544.

[Test Example 33] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Confirmation test of herbicidal activity against velvetleaf in soil treatment:
Field soil was filled in a plastic pot of about 340 cm and ³ volumes, and velvetleaf seeds were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the soil treatment, the compounds superior to the compounds B-0328 and B-0469 in the herbicidal effect on velvetleaf were the compounds B-0333 and B-0544.

[Test Example 34] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Confirmation test of herbicidal activity against Amaranthus retroflexa in soil treatment:
Field soil was filled in a plastic pot of about 340 cm and ³ volumes, and Amaranthus retroflexa seeds were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In soil treatment, the compounds superior to compounds B-0328 and B-0469 in herbicidal effect on Amaranthus retroflexa were compounds B-0333 and B-0544.

[Test Example 35] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is a chlorine atom. Test for confirming herbicidal activity against barnyard grass in
Field soil was filled in a plastic pot of about 3020 cm ³ volumes, and barnyard grass seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to the compounds B-0156 and B-0462 in the herbicidal effect on barnyard grass was compound B-0245.

[Test Example 36] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is a chlorine atom. Test for confirming herbicidal activity against oats in Japan:
The field soil was filled in a plastic pot of about 3020 cm and ³ volumes, and oat seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to the compounds B-0152, B-0156 and B-0462 in the herbicidal effect on oats was compound B-0245.

[Test Example 37] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is a chlorine atom. Weeding activity confirmation test for Alopecurus aequalis in
The field soil was filled in a plastic pot of about 3020 cm and ³ volumes, and the seeds of Alopecurus aequalis were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to the compounds B-0152, B-0153, B-0156 and B-0462 in the herbicidal effect on Alopecurus aequalis was compound B-0245.

[Test Example 38] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is a chlorine atom. Test for confirming herbicidal activity against Oinutade in
The field soil was filled in a plastic pot of about 3020 cm and ³ volumes, and seeds of Oinutade were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 16 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to the compounds B-0152 and B-0156 in the herbicidal effect on Oinutade was compound B-0245.

[Test Example 39] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is a chlorine atom. Test for confirming herbicidal activity against white goosefoot in
The field soil was filled in a plastic pot of about 3020 cm and ³ volumes, and white goosefoot seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g, 16 g or 4 g per hectare, which is equivalent to the amount of sprayed water of 1000 liters per hectare. Was sprayed on the weeds in the pot with a small sprayer. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to the compounds B-0152, B-0153, B-0156 and B-0462 in the herbicidal effect on white goosefoot was compound B-0245.

[Test Example 40] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is a chlorine atom. Weeding activity confirmation test for velvetleaf in
The field soil was filled in a plastic pot of about 3020 cm ³ volumes, and velvetleaf seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 16 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to the compounds B-0152, B-0156 and B-0462 in the herbicidal effect on velvetleaf was compound B-0245.

[Test Example 41] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is a chlorine atom. Weeding activity confirmation test for morning glory in
The field soil was filled in a plastic pot of about 3020 cm and ³ volumes, and the seeds of the morning glory were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 16 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to the compounds B-0152, B-0153, B-0156 and B-0462 in the herbicidal effect on the morning glory was compound B-0245.

[Test Example 42] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is a chlorine atom. Herbicidal activity confirmation test for Amaranthus palmeritus in
The field soil was filled in a plastic pot of about 3020 cm and ³ volumes, and the seeds of Amaranthus palmeri were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to the compounds B-0152, B-0156 and B-0462 in the herbicidal effect on Amaranthus palmeri was compound B-0245.

[Test Example 43] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , soil treatment of a compound in which R3 is a chlorine atom Test for confirming herbicidal activity against oats in Japan:
Field soil was filled in a plastic pot of about 3020 cm ³ volumes, and oat seeds were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 16 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In soil treatment, the compound superior to compounds B-0152, B-0153, B-0154 and B-0462 in herbicidal effect on oats was compound B-0245.

[Test Example 44] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , soil treatment of a compound in which R3 is a chlorine atom. Confirmation test of herbicidal activity against Alopecurus myosum:
The field soil was filled in a plastic pot of about 3020 cm and ³ volumes, and the seeds of Alopecurus aequalis were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 16 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In soil treatment, the compound superior to compounds B-0154 and B-0462 in herbicidal effect on Alopecurus aequalis was compound B-0245.

[Test Example 45] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , soil treatment of a compound in which R3 is a chlorine atom Test for confirming herbicidal activity against Oinutade in
The field soil was filled in a plastic pot of about 3020 cm ³ volumes, and seeds of Oinutade were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In soil treatment, the compound superior to compound B-0154 in herbicidal effect on Oinutade was compound B-0245.

[Test Example 46] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , soil treatment of a compound in which R3 is a chlorine atom Test of herbicidal activity against white goosefoot in
The field soil was filled in a plastic pot of about 3020 cm ³ volumes, and white goosefoot seeds were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 16 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In soil treatment, the compound superior to compounds B-0152, B-0153 and B-0154 in herbicidal effect on white goosefoot was compound B-0245.

[Test Example 47] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , soil treatment of a compound in which R3 is a chlorine atom. Weeding activity confirmation test for velvetleaf in
Field soil was filled in a plastic pot of about 3020 cm ³ volumes, and velvetleaf seeds were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 16 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In soil treatment, the compound superior to compounds B-0153, B-0154 and B-0462 in herbicidal effect on velvetleaf was compound B-0245.

[Test Example 48] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , soil treatment of a compound in which R3 is a chlorine atom. Test for confirming herbicidal activity against ragweed in
The field soil was filled in a plastic pot of about 3020 cm ³ volumes, and ragweed seeds were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In soil treatment, the compound superior to compounds B-0152, B-0153, B-0154 and B-0462 in herbicidal effect on ragweed was compound B-0245.

[Test Example 49] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is an iodine atom. Weeding activity confirmation test for Alopecurus aequalis in
The field soil was filled in a plastic pot of about 3020 cm and ³ volumes, and the seeds of Alopecurus aequalis were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to compound B-0349 in herbicidal effect on Alopecurus aequalis was compound B-0309.

[Test Example 50] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is an iodine atom. Test for confirming herbicidal activity against white goosefoot in
The field soil was filled in a plastic pot of about 3020 cm and ³ volumes, and white goosefoot seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 4 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to compound B-034 in herbicidal effect on white goosefoot was compound B-0309.

[Test Example 51] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is an iodine atom. Weeding activity confirmation test for velvetleaf in
The field soil was filled in a plastic pot of about 3020 cm ³ volumes, and velvetleaf seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to compound B-034 in herbicidal effect on velvetleaf was compound B-0309.

[Test Example 52] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is an iodine atom. Weeding activity confirmation test for morning glory in
The field soil was filled in a plastic pot of about 3020 cm and ³ volumes, and the seeds of the morning glory were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 16 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to the compound B-034 in the herbicidal effect on the morning glory was the compound B-0309.

[Test Example 53] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is an iodine atom. Herbicidal activity confirmation test for Amaranthus palmeritus in
The field soil was filled in a plastic pot of about 3020 cm and ³ volumes, and the seeds of Amaranthus palmeri were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to compound B-0304 in the herbicidal effect on Amaranthus palmeri was compound B-0309.

[Test Example 54] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is a cyano group. Test of herbicidal activity against white goosefoot in
The field soil was filled in a plastic pot of about 3020 cm and ³ volumes, and white goosefoot seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 16 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to compound B-0369 in the herbicidal effect on white goosefoot was compound B-0376.

[Test Example 55] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is a cyano group. Weeding activity confirmation test for velvetleaf in
The field soil was filled in a plastic pot of about 3020 cm ³ volumes, and velvetleaf seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 16 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to compound B-0369 in herbicidal effect on velvetleaf was compound B-0376.

[Test Example 56] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , soil treatment of a compound in which R3 is a cyano group is used. Test for confirming herbicidal activity against white goosefoot in
The field soil was filled in a plastic pot of about 3020 cm ³ volumes, and white goosefoot seeds were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 16 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In soil treatment, the compound superior to compound B-0369 in herbicidal effect on white goosefoot was compound B-0376.

[Test Example 57] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , soil treatment of the compound in which R3 is a cyano group is used. Weeding activity confirmation test for velvetleaf in
Field soil was filled in a plastic pot of about 3020 cm ³ volumes, and velvetleaf seeds were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In soil treatment, the compound superior to compound B-0369 in herbicidal effect against velvetleaf was compound B-0376.

[Test Example 58] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Confirmation test of herbicidal activity against barnyard grass in foliage treatment:
Field soil was filled in a plastic pot of about 3020 cm ³ volumes, and barnyard grass seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compounds superior to the compounds B-0328 and B-0469 in the herbicidal effect on barnyard grass were the compounds B-0333 and B-0544.

[Test Example 59] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Confirmation test of herbicidal activity against Alopecurus aequalis in foliage treatment:
The field soil was filled in a plastic pot of about 3020 cm and ³ volumes, and the seeds of Alopecurus aequalis were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to the compounds B-0328 and B-0469 in the herbicidal effect on Alopecurus aequalis was B-0544.

[Test Example 60] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Confirmation test of herbicidal activity against Oinutade in foliage treatment:
The field soil was filled in a plastic pot of about 3020 cm and ³ volumes, and seeds of Oinutade were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compounds superior to compounds B-0328 and B-0469 in the herbicidal effect on Oinutade were compounds B-0333 and B-0544.

[Test Example 61] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Confirmation test of herbicidal activity against white goosefoot in foliage treatment:
The field soil was filled in a plastic pot of about 3020 cm and ³ volumes, and white goosefoot seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 4 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compounds superior to the compounds B-0328 and B-0469 in the herbicidal effect on white goosefoot were the compounds B-0333 and B-0544.

[Test Example 62] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Confirmation test of herbicidal activity against velvetleaf in foliage treatment:
The field soil was filled in a plastic pot of about 3020 cm ³ volumes, and velvetleaf seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 16 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compounds superior to the compounds B-0328 and B-0469 in the herbicidal effect on velvetleaf were the compounds B-0333 and B-0544.

[Test Example 63] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Confirmation test of herbicidal activity against morning glory in foliage treatment:
The field soil was filled in a plastic pot of about 3020 cm and ³ volumes, and the seeds of the morning glory were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compounds superior to the compounds B-0328 and B-0469 in the herbicidal effect on the morning glory were the compounds B-0333 and B-0544.

[Test Example 64] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Herbicidal activity confirmation test for Amaranthus palmeri in foliage treatment:
The field soil was filled in a plastic pot of about 3020 cm and ³ volumes, and the seeds of Amaranthus palmeri were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 4 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compounds superior to the compounds B-0328 and B-0469 in the herbicidal effect on Amaranthus palmeri were the compounds B-0333 and B-0544.

[Test Example 65] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Confirmation test of herbicidal activity against oats in soil treatment:
Field soil was filled in a plastic pot of about 3020 cm ³ volumes, and oat seeds were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In soil treatment, the compound superior to compound B-0328 in herbicidal effect on oats was compound B-0333.

[Test Example 66] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Confirmation test of herbicidal activity against Alopecurus aequalis in soil treatment:
The field soil was filled in a plastic pot of about 3020 cm and ³ volumes, and the seeds of Alopecurus aequalis were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g or 16 g per hectare, and the equivalent of 1000 liters of sprayed water per hectare is applied to the soil with a small sprayer. It was sprayed on the entire surface. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In soil treatment, compounds B-0333 and B-0544 were superior to compound B-0328 in herbicidal effect on Alopecurus aequalis.

[Test Example 67] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Confirmation test of herbicidal activity against Oinutade in soil treatment:
The field soil was filled in a plastic pot of about 3020 cm ³ volumes, and seeds of Oinutade were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

Compounds B-0333 and B-0544 were superior to compound B-0328 in herbicidal effect on soil treatment.

[Test Example 68] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Confirmation test of herbicidal activity against white goosefoot in soil treatment:
The field soil was filled in a plastic pot of about 3020 cm ³ volumes, and white goosefoot seeds were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 16 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In soil treatment, the compound superior to compound B-0328 in herbicidal effect on white goosefoot was compound B-0544.

[Test Example 69] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Confirmation test of herbicidal activity against velvetleaf in soil treatment:
Field soil was filled in a plastic pot of about 3020 cm ³ volumes, and velvetleaf seeds were sown at a sowing depth of 1 cm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In soil treatment, the compound superior to compound B-0328 in herbicidal effect on velvetleaf was compound B-0544.

[Test Example 70] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , soil treatment of a compound in which R3 is a chlorine atom Test for confirming herbicidal activity against green foxtail:
The field soil was filled in a plastic pot of about 1270 cm ³ volumes, and the seeds of green foxtail were sown at a sowing depth of 5 mm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 38 g per hectare, and the amount equivalent to 200 liters of water per hectare is applied to the entire surface of the soil with an automatic spraying device. It was sprayed on. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In soil treatment, the compound superior to compound B-0152 in herbicidal effect on green foxtail was compound B-0245.
[Test Example 71] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , soil treatment of a compound in which R3 is a chlorine atom Weeding activity confirmation test for Amaranthus retroflexus in
Field soil was filled in a plastic pot of about 1270 cm ³ volumes, and Amaranthus retroflexa seeds were sown at a sowing depth of 5 mm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 38 g per hectare, and the amount equivalent to 200 liters of water per hectare is applied to the entire surface of the soil with an automatic spraying device. It was sprayed on. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In soil treatment, the compound superior to compound B-0152 in herbicidal effect on Amaranthus retroflexa was compound B-0245.

[Test Example 72] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is an iodine atom. Weeding activity confirmation test for Amaranthus retroflexus in
The field soil was filled in a plastic pot of about 1270 cm ³ volumes, and Amaranthus retroflexa seeds were sown at a sowing depth of 5 mm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 50 g per hectare, and an amount equivalent to 200 liters of sprayed water per hectare is automatically sprayed. The foliage was sprayed on the weeds in the pot with the device. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to compound B-0304 in herbicidal effect on Amaranthus retroflexa was compound B-0309.

[Test Example 73] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is an iodine atom. Test for confirming herbicidal activity against nightshade in Japan:
Field soil was filled in a plastic pot of about 1270 cm ³ volumes, and nightshade seeds were sown at a sowing depth of 5 mm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 50 g per hectare, and an amount equivalent to 200 liters of sprayed water per hectare is automatically sprayed. The foliage was sprayed on the weeds in the pot with the device. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to compound B-034 in herbicidal effect on nightshade was compound B-0309.

[Test Example 74] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the foliage treatment of the compound in which R3 is an iodine atom. Test for confirming herbicidal activity against white goosefoot in
The field soil was filled in a plastic pot of about 1270 cm ³ volumes, and white goosefoot seeds were sown at a sowing depth of 5 mm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 50 g per hectare, and an amount equivalent to 200 liters of sprayed water per hectare is automatically sprayed. The foliage was sprayed on the weeds in the pot with the device. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

[Test Example 75] Of the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , soil treatment of the compound in which R3 is a cyano group is used. Weeding activity confirmation test for Amaranthus retroflexus in
Field soil was filled in a plastic pot of about 1270 cm ³ volumes, and Amaranthus retroflexa seeds were sown at a sowing depth of 5 mm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 50 g per hectare, and the amount equivalent to 200 liters of water per hectare is applied to the entire surface of the soil with an automatic spraying device. It was sprayed on. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In soil treatment, the compound superior to compound B-0369 in herbicidal effect on Amaranthus retroflexa was compound B-0376.

[Test Example 76] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Confirmation test of herbicidal activity against Amaranthus retroflexa in foliage treatment:
A plastic pot of about 1270 cm ³ volumes was filled with clay, and Amaranthus retroflexa seeds were sown at a sowing depth of 5 mm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 50 g per hectare, and an amount equivalent to 200 liters of sprayed water per hectare is automatically sprayed. The foliage was sprayed on the weeds in the pot with the device. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to compound B-0328 in herbicidal effect on Amaranthus retroflexa was compound B-0544.

[Test Example 77] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Confirmation test of herbicidal activity against nightshade in foliage treatment:
Field soil was filled in a plastic pot of about 1270 cm ³ volumes, and nightshade seeds were sown at a sowing depth of 5 mm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 50 g per hectare, and an amount equivalent to 200 liters of sprayed water per hectare is automatically sprayed. The foliage was sprayed on the weeds in the pot with the device. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In the foliage treatment, the compound superior to compound B-0328 in herbicidal effect on nightshade was compound B-0544.

[Test Example 78] Among the compounds of the present invention shown in Tables 3 to 16 and Tables 40 to 43 in which Q in the general formula [I] is Q- ² , the compound in which R3 is a trifluoromethyl group Confirmation test of herbicidal activity against Amaranthus retroflexa in soil treatment:
Field soil was filled in a plastic pot of about 1270 cm ³ volumes, and Amaranthus retroflexa seeds were sown at a sowing depth of 5 mm. The wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 150 g per hectare, and the amount equivalent to 200 liters of water per hectare is applied to the entire surface of the soil with an automatic spraying device. It was sprayed on. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.

In soil treatment, the compounds superior to compound B-0328 in herbicidal effect on Amaranthus retroflexa were compounds B-0333 and B-0544.

The present invention provides a novel compound having excellent herbicidal activity and a production intermediate thereof, is useful in the fields of agrochemicals and agriculture, and has the possibility of industrial use.

Claims

General formula [I]

[In the general formula [I],
Q indicates Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7 or Q-8.

R 1 is a hydrogen atom, a C 1 to C 6 alkyl group (the group may be mono-substituted or poly-substituted by R 8 ), a C 2 -C 6 alkenyl group (the group may be mono-substituted or poly-substituted by R 8 ). Substituted) , C2 - C6 alkynyl group (the group may be mono-substituted or poly - substituted with R8), C3 - C6 cycloalkyl group ( the group may be mono-substituted or poly-substituted with R8). Indicates a poly-substituted), phenyl group (the group may be mono- or poly-substituted by R 9 ) or a heteroaryl group (the group may be mono- or poly-substituted by R 9 ). ,
R 8 is a halogen atom, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, C 3 to C 6 cycloalkyl group, C 3 to C 6 halocycloalkyl group, formyl group, C 1 to C 6 Alkylcarbonyl group, C1 to C6 haloalkylcarbonyl group, C3 to C6 cycloalkylcarbonyl group, benzoyl group (the group may be mono- or poly-substituted with R 9 ) , -C (R 10 ) = NOR 11 , carboxy group, C 1 to C 6 alkoxycarbonyl group, C 1 to C 6 haloalkoxycarbonyl group, aminocarbonyl group, C1 to C6 alkylaminocarbonyl group (even if the amino group is substituted with R12 ) Good), C 1-6 haloalkylaminocarbonyl group (the amino group may be substituted with R 12 ), pyrrolidine- 1 -ylcarbonyl group (the group may be mono-substituted or poly-substituted with R 9 ). ), Piperidine-1-ylcarbonyl group (the group may be mono-substituted or poly-substituted with R 9 ), hydroxy group, C 1 to C 6 alkoxy group, C 3 to C 6 alkenyloxy group, C 3 to C 6 alkynyloxy group, C 1 to C 6 haloalkoxy group, C 3 to C 6 cycloalkoxy group, C 3 to C 6 halocycloalkoxy group, C 3 to C 6 cycloalkyl C 1 to C 6 alkoxy group, C 3 to C 6 halocycloalkyl C 1 to C 6 alkoxy group, phenoxy group (the group may be mono-substituted or poly-substituted with R 9 ), phenyl C 1 to C 6 alkoxy group (the phenyl group is R 9 ). ( Can be mono - substituted or poly - substituted with C1 to C6 haloalkylsulfinyl groups , C1 to C6 haloalkylsulfonyl groups , C3 to C6 cycloalkylthio groups , C3 to C6 cycloalkylsulfinyl groups, C3 to C6 cycloalkylsulfonyl groups , C3 to C 6 halocycloalkylthio group , C3 to C6 halocycloalkylsulfinyl group , C3 to C6 halocycloalkylsulfonyl group , C3 to C6 cycloalkyl C1 to C6 alkylthio group, C3 to C6cyclo Alkyl C 1 to C 6 alkyl sulfinyl groups, C 3 to C 6 cycloalkyl C 1 to C 6 alkyl sulfonyl groups, C 3 to C 6 halocycloalkyl C 1 to C 6 alkylthio groups, C 3 to C 6 halocycloalkyl C 1 ~ C 6 alkyl sulfinyl group, C 3 ~ C 6 halocycloalkyl C 1 ~ C 6 alkyl sulfonyl group, phenylthio group (the group may be mono-substituted or poly-substituted by R9), phenyl sulfinyl group (the group). May be mono-substituted or poly-substituted with R 9 ), a phenylsulfonyl group (the group may be mono- or poly - substituted with R 9 ), an amino group, a C1-6 alkylamino group (the amino). The group may be substituted with R 12 ), a C 1 to C 6 haloalkylamino group (the amino group may be substituted with R 12 ), a C 1 to C 6 alkylcarbonylamino group (the amino group may be R 12). 12 may be substituted) , C 1 to C 6 haloalkylcarbonylamino groups (the amino groups may be substituted by R12 ), C3 to C6 cycloalkylcarbonylamino groups (the amino groups may be R12 ). (May be substituted with R 9 ), phenylcarbonylamino group (the phenyl group may be mono-substituted or poly-substituted with R 9, and the amino group may be substituted with R 12 ), C 1 to C 6 alkoxy. A carbonylamino group (the amino group may be substituted with R 12 ), a C 1 to C 6 haloalkoxycarbonyl amino group (the amino group may be substituted with R 12 ), a C 1 to C 6 alkylamino. A carbonylamino group (the amino group may be substituted with R 12 ), a C 1 to C 6 haloalkylaminocarbonylamino group (the amino group may be substituted with R 12 ), a C 1 to C 6 alkylsulfonyl. Amino group (the amino group may be substituted with R 12 ), C 1 to C 6 haloalkylsulfonylamino group (the amino group may be substituted with R 12 ), C 3 to C 6 cycloalkylsulfonylamino. A group (the amino group may be substituted with R 12 ), a phenylsulfonyl amino group (the phenyl group may be mono-substituted or poly-substituted with R 9 , and the amino group may be substituted with R 12 ). ), Tri (C 1 to C 6 alkyl) silyl group, phenyl group (the group is motorized by R9) No-substituted or poly-substituted), 1,3-benzodioxolyl group (the group may be mono-substituted or poly-substituted with R 9 ), heteroaryl group (the group may be mono-substituted with R 9 ). Alternatively, it may be poly-substituted), a heteroaryloxy group (the group may be mono-substituted or poly-substituted with R 9 ), a heterocycloalkyl group (the group may be mono- or poly-substituted with R 9 ). Good), showing a cyano group, a nitro group or a thiocyanato group,
R 9 is a halogen atom, C 1 to C 6 alkyl group, C 2 to C 6 alkenyl group, C 2 to C 6 alkynyl group, C 1 to C 6 haloalkyl group, C 3 to C 6 cycloalkyl group, C 3 ~ C 6 halocycloalkyl group, formyl group, hydroxy group, C 1 ~ C 6 alkoxy group, C 1 ~ C 6 haloalkoxy group, thiol group, C 1 ~ C 6 alkylthio group, C 1 ~ C 6 alkyl sulfinyl group , C 1 to C 6 alkylsulfonyl groups, C 1 to C 6 haloalkylthio groups, C1 to C6 haloalkylsulfinyl groups, C1 to C6 haloalkylsulfonyl groups, cyano groups or nitro groups.
R 10 is a hydrogen atom, C 1 to C 6 alkyl group, C 2 to C 6 alkenyl group, C 2 to C 6 alkynyl group, C 1 to C 6 haloalkyl group, C 3 to C 6 cycloalkyl group, phenyl group. (The group may be mono-substituted or poly-substituted with R 9 ) or a heteroaryl group (the group may be mono- or poly-substituted with R 9 ).
R 11 is a hydrogen atom, C 1 to C 6 alkyl group, C 2 to C 6 alkenyl group, C 2 to C 6 alkynyl group, C 1 to C 6 haloalkyl group, C 3 to C 6 cycloalkyl group or C 3 Representing a ~ C6 halocycloalkyl group,
R 12 is a C 1 to C 6 alkyl group, a C 2 to C 6 alkenyl group, a C 2 to C 6 alkynyl group, a C 1 to C 6 haloalkyl group, a C 3 to C 6 cycloalkyl group, and a C 3 to C 6 . Halocycloalkyl group, C3 to C6 cycloalkyl C1 to C6 alkyl group, C1 to C 6alkoxy C1 to C6 alkyl group, C1 to C 6 haloalkoxy C1 to C6 alkyl group, cyano C 1 to C 6 alkyl groups, C 1 to C 6 alkyl carbonyl groups, C 1 to C 6 haloalkyl carbonyl groups, C 1 to C 6 alkoxycarbonyl groups, C 1 to C 6 halo alkoxycarbonyl groups, C 1 to C 6 An alkylaminocarbonyl group, a C1 to C6 haloalkylaminocarbonyl group or a benzoyl group (the group may be mono - substituted or poly - substituted by R9) is shown.
R 2 is a hydrogen atom, a halogen atom, a C 1 to C 6 alkyl group, a C 2 to C 6 alkenyl group, a C 2 to C 6 alkynyl group, a C 1 to C 6 haloalkyl group, and a C 3 to C 6 cycloalkyl group. , C 3 to C 6 halocycloalkyl groups, formyl groups , C 1 to C 6 alkylcarbonyl groups, C1 to C6 haloalkylcarbonyl groups, C3 to C6 cycloalkylcarbonyl groups, -C (R 10 ) = NOR 11 , carboxy group, C 1 to C 6 alkoxycarbonyl group, C 1 to C 6 haloalkoxycarbonyl group, aminocarbonyl group, aminothiocarbonyl group, C1 to C6 alkylaminocarbonyl group (the amino group is based on R12 ). C1 to C6 haloalkylaminocarbonyl group (the amino group may be substituted by R12 ), hydroxy group, C1 to C6 alkoxy group , C3 to C6 alkenyloxy group. , C 3 to C 6 alkynyloxy groups, C 1 to C 6 haloalkoxy groups, C 3 to C 6 cycloalkoxy groups, C 3 to C 6 halocycloalkoxy groups, C 3 to C 6 cycloalkyls C 1 to C 6 Alkoxy groups, C 3 to C 6 halocycloalkyl C 1 to C 6 alkoxy groups, phenyl C 1 to C 6 alkoxy groups (the phenyl groups may be mono-substituted or poly-substituted by R9), heteroaryloxy groups. (The group may be mono-substituted or poly-substituted with R 9 ), C 1 to C 6 alkylthio groups, C 1 to C 6 alkyl sulfinyl groups, C 1 to C 6 alkyl sulfonyl groups, C 1 to C 6 halos. Alkylthio groups, C1 to C6 haloalkylsulfinyl groups, C1 to C6 haloalkylsulfonyl groups, amino groups, C1 to C6 alkylamino groups (the amino groups may be substituted with R12 ), C1 to C 6 haloalkylamino group (the amino group may be substituted with R 12 ), C 1 to C 6 alkylcarbonylamino groups (the amino group may be substituted with R 12 ), C 1 to C 6 haloalkyl. A carbonylamino group (the amino group may be substituted with R 12 ), a C 3 to C 6 cycloalkylcarbonyl amino group (the amino group may be substituted with R 12 ), a C 1 to C 6 alkoxycarbonyl. Amino group (the amino group is R 12 may be substituted), C 1 to C 6 alkylsulfonylamino groups (the amino groups may be substituted by R 12 ), C 1 to C 6 haloalkylsulfonyl amino groups (the amino groups may be substituted by R 12 ). Substituted), C 3 - C6 cycloalkylsulfonylamino group (the amino group may be substituted with R 12 ), phenyl group (the group may be mono-substituted or poly-substituted with R 9 ). ), Heteroaryl group (the group may be mono-substituted or poly-substituted by R9), cyano group or nitro group.
R 3 is a hydrogen atom, a halogen atom, a C 1 to C 6 alkyl group, a C 2 to C 6 alkoxy group, a C 2 to C 6 alkoxyyl group , a C 1 to C 6 haloalkyl group, and a C 3 to C 6 cycloalkyl group. , C 3 to C 6 halocycloalkyl groups, C 1 to C 6 alkoxy C 1 to C 6 alkyl groups, C 1 to C 6 haloalkoxy C 1 to C 6 alkyl groups, C 1 to C 6 alkylthios C 1 to C 6 Alkoxy Group, C 1 to C 6 Alkoxy Sulfinyl C 1 to C 6 Alkoxy Group, C 1 to C 6 Alkoxysulfonyl C 1 to C 6 Alkoxy Group, C 1 to C 6 Haloalkylthio C 1 to C 6 Alkoxy Group, C 1 to C 6 haloalkylsulfinyl C 1 to C 6 alkyl groups, C 1 to C 6 haloalkylsulfonyl C 1 to C 6 alkyl groups, cyano C 1 to C 6 alkyl groups, formyl groups, C 1 to C 6 alkyl carbonyl groups, C 1 to C 6 haloalkyl carbonyl group, C 3 to C 6 cycloalkyl carbonyl group, -C (R 10 ) = NOR 11 , carboxy group, C 1 to C 6 alkoxy carbonyl group, C 1 to C 6 haloalkoxy carbonyl group , Aminocarbonyl group, aminothiocarbonyl group, C1 to C6 alkylaminocarbonyl group (the amino group may be substituted with R12 ), C1 to C6 haloalkylaminocarbonyl group (the amino group is R12 ). , Hydroxyl group, C1 to C6 alkoxy group, C3 to C6 alkoxyoxy group , C3 to C6 alkynyloxy group , C1 to C6 haloalkoxy group , C3 to C 6 cycloalkoxy groups, C 3 to C 6 halocycloalkoxy groups, C 3 to C 6 cycloalkyl C 1 to C 6 alkoxy groups, C 3 to C 6 halocycloalkyl C 1 to C 6 alkoxy groups, phenyl C 1 to C 6 alkoxy group (the phenyl group may be mono-substituted or poly-substituted with R 9 ), heteroaryloxy group (the group may be mono-substituted or poly-substituted with R 9 ), C 1 -C 6 Alkoxythio groups , C1 to C6 alkylsulfinyl groups, C1 to C6 alkylsulfonyl groups, C1 to C6 haloalkylthio groups, C1 to C6 haloalkylsulfinyl groups, C1 to C6 haloalkylsulfoni Lu groups, amino groups, C 1 to C 6 alkylamino groups (the amino groups may be substituted with R 12 ), C 1 to C 6 haloalkyl amino groups (the amino groups may be substituted with R 12 ). ), C 1 to C 6 alkylcarbonylamino groups (the amino groups may be substituted with R12 ), C1 to C6 haloalkylcarbonylamino groups (the amino groups may be substituted with R12 ), C 3 to C 6 cycloalkylcarbonylamino groups (the amino groups may be substituted with R12 ), C1 to C6 alkoxycarbonylamino groups (the amino groups may be substituted with R12 ), C. 1 to C 6 alkylsulfonylamino groups (the amino groups may be substituted with R12 ), C1 to C6 haloalkylsulfonylamino groups (the amino groups may be substituted with R12 ) , C3 to C6 cycloalkylsulfonylamino group (the amino group may be substituted with R 12 ), phenyl group (the group may be mono-substituted or poly-substituted with R 9 ) , heteroaryl group (the group may be R). 9 ), mono- or poly-substituted), showing a cyano or nitro group,
R4 is independently a halogen atom, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, hydroxy group, C 1 to C 6 alkoxy group, C 1 to C 6 haloalkoxy group, cyano group or nitro. Show the group,
m represents an integer of 0, 1, 2 or 3
Y represents an oxygen atom or a sulfur atom.
R 5 independently contains a hydrogen atom, a halogen atom, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a C 3 to C 6 cycloalkyl group, a C 3 to C 6 halocycloalkyl group, and a hydroxy group. , C 1 to C 6 alkoxy groups, C 1 to C 6 haloalkoxy groups, heteroaryloxy groups (the groups may be mono- or poly-substituted with R 9 ), tri (C 1 to C 6 alkyl) silyloxy. It represents a group or a cyano group, and the two R5s may be combined to form an oxo group (= O), or a C1 to C6 alkoxyimino group, and the two R5s are bound to each other. Select from a 3- to 6-membered carbocycle, or a nitrogen atom, an oxygen atom, and a sulfur atom (the sulfur atom may be substituted with one or two oxo groups (= O)) together with these bonded carbon atoms. A 3- to 6-membered heterocycle having 1 to 4 heteroatoms may be formed.
R 6 is a hydrogen atom, C 1 to C 6 alkyl group, C 2 to C 6 alkenyl group, C 2 to C 6 alkynyl group, C 1 to C 6 haloalkyl group, C 3 to C 6 cycloalkyl group, C 3 ~ C 6 halocycloalkyl group, C 3 ~ C 6 cycloalkyl C 1 ~ C 6 alkyl group, C 1 ~ C 6 alkoxy C 1 ~ C 6 alkyl group, C 1 ~ C 6 haloalkoxy C 1 ~ C 6 alkyl Group, cyano C 1 to C 6 alkyl group, C 1 to C 6 alkyl carbonyl group, C 1 to C 6 alkoxycarbonyl group or C 1 to C 6 alkyl sulfonyl group.
R 7 is a halogen atom, C 1 to C 6 alkyl group, C 2 to C 6 alkenyl group, C 2 to C 6 alkynyl group, C 1 to C 6 haloalkyl group, C 3 to C 6 cycloalkyl group, C 3 ~ C 6 halocycloalkyl group, hydroxy group, C 1 ~ C 6 alkoxy group, C 1 ~ C 6 haloalkoxy group, C 1 ~ C 6 alkylthio group, C 1 ~ C 6 alkyl sulfinyl group, C 1 ~ C 6 Indicates an alkylsulfonyl group, a C1 to C6 haloalkylthio group, a C1 to C6 haloalkylsulfinyl group, a C1 to C6 haloalkylsulfonyl group, a cyano group or a nitro group.
Z represents an oxygen atom or a sulfur atom.
A indicates N or CR 13 .
R 13 represents a hydrogen atom, a halogen atom or a cyano group]
Condensed heterocyclic derivative represented by, or an agriculturally acceptable salt thereof.
R 1 is a hydrogen atom, a C 1 to C 6 alkyl group (the group may be mono-substituted or poly-substituted by R 8 ), a C 2 -C 6 alkenyl group (the group may be mono-substituted or poly-substituted by R 8 ). Substituted), C2 - C6 alkynyl group (the group may be mono-substituted or poly-substituted with R 8 ), phenyl group (the group may be mono- or poly-substituted with R 9 ). ) Or a heteroaryl group (the group may be mono-substituted or poly-substituted by R9 ).
R 8 is a halogen atom, C 1 to C 6 haloalkyl group, C 3 to C 6 cycloalkyl group, C 3 to C 6 halocycloalkyl group, benzoyl group (the group is mono-substituted or poly-substituted by R 9 ). C 1 to C 6 alkoxycarbonyl group, C 1 to C 6 alkoxy group, C 1 to C 6 haloalkoxy group, C 3 to C 6 cycloalkoxy group, C 3 to C 6 halocycloalkoxy group, C 3 to C 6 cycloalkyl C 1 to C 6 alkoxy group, phenoxy group (the group may be mono-substituted or poly-substituted with R 9 ), C 1 to C 6 haloalkyl thio group, C 1 to C 6 haloalkyl sulfinyl. Group, C 1 to C 6 haloalkylsulfonyl group, phenylthio group (the group may be mono-substituted or poly-substituted with R 9 ), phenylsulfinyl group (the group may be mono-substituted or poly-substituted with R 9 ). ), Phenylsulfonyl group (the group may be mono-substituted or poly-substituted with R 9 ), phenylsulfonyl amino group (the phenyl group may be mono-substituted or poly-substituted with R 9 ), the amino group may be R (May be substituted with 12 ), phenyl group (the group may be mono-substituted or poly-substituted with R 9 ), heteroaryl group (the group may be mono- or poly-substituted with R 9 ),. A heteroaryloxy group (the group may be mono-substituted or poly-substituted with R 9 ), a heterocycloalkyl group (the group may be mono-substituted or poly-substituted with R 9 ), a cyano group or a thiocyanato group. Show,
R 9 represents a halogen atom, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a formyl group, a C 1 to C 6 alkoxy group, a C 1 to C 6 haloalkoxy group, a cyano group or a nitro group. ,
R 10 indicates a hydrogen atom and represents a hydrogen atom.
R 11 represents a C 1 to C 6 alkyl group.
R 12 represents a C 1 to C 6 alkyl group.
R 2 represents a hydrogen atom, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a C 1 to C 6 alkoxycarbonyl group, an aminocarbonyl group or a cyano group.
R 3 is a hydrogen atom, a halogen atom, a C 1 to C 6 alkyl group, a C 2 to C 6 alkenyl group, a C 1 to C 6 haloalkyl group, a C 3 to C 6 cycloalkyl group, and a C 1 to C 6 alkoxy C. 1 to C 6 alkyl groups, C 1 to C 6 alkylthio C 1 to C 6 alkyl groups, C 1 to C 6 alkyl sulfinyl C 1 to C 6 alkyl groups, C 1 to C 6 alkyl sulfonyl C 1 to C 6 alkyl groups , C 1 to C 6 haloalkylthio C 1 to C 6 alkyl groups, C 1 to C 6 haloalkylsulfinyl C 1 to C 6 alkyl groups, C 1 to C 6 haloalkylsulfonyl groups 1 to C 6 alkyl groups, formyl groups,- C (R 10 ) = NOR 11 , aminocarbonyl group, C 1 to C 6 alkoxy group, C 1 to C 6 haloalkoxy group, heteroaryloxy group (the group may be mono-substituted or poly-substituted by R 9 ). ), C 1 to C 6 alkylthio groups, C 1 to C 6 alkyl sulfinyl groups, C 1 to C 6 alkyl sulfonyl groups, C 1 to C 6 alkyl amino groups (the amino groups may be substituted with R 12 ). , A phenyl group (the group may be mono- or poly-substituted by R9 ) or a cyano group.
R 4 represents a halogen atom or a C 1 to C 6 alkyl group.
m represents an integer of 0 or 1 and represents
Y represents an oxygen atom or a sulfur atom.
R 5 is independently a halogen atom, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, hydroxy group, C 1 to C 6 alkoxy group, C 1 to C 6 halo alkoxy group, heteroaryloxy group. (The group may be mono-substituted or poly-substituted with R 9 ) or a tri (C 1 to C 6 alkyl) silyloxy group, and the two R 5s together are an oxo group (= O), or C 1 to C 6 alkoxyimino groups may be formed, and the two R 5s may be bonded to each other to form a 3- to 6-membered carbon ring together with these bonded carbon atoms, or a nitrogen atom, an oxygen atom and a sulfur atom. A 3- to 6-membered heterocycle having 1 to 4 heteroatoms selected from (the sulfur atom may be substituted with 1 or 2 oxo groups (= O)) may be formed.
R 6 represents a C 1 to C 6 alkyl group or a C 1 to C 6 haloalkyl group.
R 7 represents a halogen atom, a C1 to C6 haloalkyl group or a cyano group.
Z is the condensed heterocyclic derivative according to claim 1, which represents an oxygen atom, or an agriculturally acceptable salt thereof.
In the general formula [I], Q represents Q-1, Q-2, Q-3 or Q-4.
R 1 represents a C 1 to C 6 alkyl group (the group may be mono- or poly-substituted by R 8 ).
R 8 is a C 3 to C 6 cycloalkyl group, a C 3 to C 6 halocycloalkyl group, a benzoyl group (the group may be mono-substituted or poly-substituted by R 9 ), C 1 to C 6 alkoxycarbonyl. Group, C 3 to C 6 cycloalkoxy group, C 3 to C 6 halocycloalkoxy group, C 3 to C 6 cycloalkyl C 1 to C 6 alkoxy group, phenoxy group (the group is mono-substituted or poly-substituted by R 9 ). C 1 to C 6 haloalkylthio groups, C1 to C6 haloalkylsulfinyl groups, C1 to C6 haloalkylsulfonyl groups, phenylthio groups (the groups may be mono-substituted or poly-substituted by R9). (Good), phenylsulfinyl group (the group may be mono-substituted or poly-substituted with R 9 ), phenylsulfonyl group (the group may be mono- or poly-substituted with R 9 ), phenylsulfonylamino group (may be). The phenyl group may be mono-substituted or poly-substituted with R 9 , the amino group may be substituted with R 12 ), a phenyl group (the group may be mono- or poly-substituted with R 9 ). , Heteroaryl group (the group may be mono-substituted or poly-substituted with R 9 ), heteroaryloxy group (the group may be mono-substituted or poly-substituted with R 9 ), heterocycloalkyl group (the group may be mono-substituted or poly-substituted). The group may be mono-substituted or poly-substituted by R9), the fused heterocyclic derivative according to claim 2 , which exhibits a cyano group or a thiocyanato group, or an agriculturally acceptable salt thereof.
In the general formula [I], R 8 is a phenyl group (the group may be mono-substituted or poly-substituted by R 9 ), a heteroaryl group (the group may be mono- or poly-substituted by R 9 ). ), The fused heterocyclic derivative according to claim 3, or an agriculturally acceptable salt thereof.
In the general formula [I], Q is the condensed heterocyclic derivative according to claim 3, which represents Q-1, or an agriculturally acceptable salt thereof.
In the general formula [I], Q is the condensed heterocyclic derivative according to claim 3 or 4, which represents Q-2, or an agriculturally acceptable salt thereof.
In the general formula [I], Q is the condensed heterocyclic derivative according to claim 3 or 4, which represents Q-3, or an agriculturally acceptable salt thereof.
In the general formula [I], Q is the condensed heterocyclic derivative according to claim 3, which represents Q-4, or an agriculturally acceptable salt thereof.
In the general formula [I], Q is the condensed heterocyclic derivative according to claim 1 or 2, which represents Q-5, Q-6, Q-7 or Q-8, or an agriculturally acceptable salt thereof.
In the general formula [I], Q is the condensed heterocyclic derivative according to claim 1 or 2, which represents Q-5, or an agriculturally acceptable salt thereof.
In the general formula [I], Q is the condensed heterocyclic derivative according to claim 1 or 2, which represents Q-6, or an agriculturally acceptable salt thereof.
In the general formula [I], Q is the condensed heterocyclic derivative according to claim 1 or 2, which represents Q-7, or an agriculturally acceptable salt thereof.
In the general formula [I], Q is the condensed heterocyclic derivative according to claim 1, which represents Q-8, or an agriculturally acceptable salt thereof.
A pesticide composition containing the condensed heterocyclic derivative according to any one of claims 1 to 13 or an agriculturally acceptable salt thereof as an active ingredient.
The pesticide composition according to claim 14, further containing a surfactant.
A herbicide containing the condensed heterocyclic derivative according to any one of claims 1 to 13 or an agriculturally acceptable salt thereof as an active ingredient.
Herbicidal effect on weeds growing in upland fields, paddy fields, orchards, turflands, non-agricultural lands, greenhouses, nursery facilities, or plant factories that grow useful plants for agricultural, horticultural and industrial uses. The herbicide according to claim 16.
The herbicide according to claim 17, wherein the useful plant having agricultural, horticultural and industrial uses is a trait plant in cultivation by a breeding method or a gene recombination technique.