JP2006282552A - Phenylheteroaryls or their salts and herbicide comprising the same as active ingredient - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain a new herbicide that has high safety to crops and excellent herbicidal activity against weeds. <P>SOLUTION: The herbicide comprises a phenylheteroaryl represented by general formula (I) (R<SP>1</SP>is H, an alkyl, an alkenyl, an alkynyl, an alkoxy, a (substituted)phenyl, a (substituted)phenyl 1-8C alkyl, a (substituted)phenylamino, a (substituted)phenoxy or the like; R<SP>2</SP>is H, an alkyl, an alkenyl, an alkylcarbonyl, an alkyl sulfonyl or the like; R<SP>3</SP>is a halogen, an alkyl, a haloalkyl, an alkoxy, a haloalkoxy, pentafluorosulfanyl (-SF<SB>5</SB>), an alkyl sulfinyl or the like; G is -C(=O)-, -C(=S)- or a -C(R<SP>6</SP>)<SB>2</SB>-; X is a single bond, -C(=O)-, -C(=S)- or -SO<SB>q</SB>-: Y is a CR<SP>7</SP>or N→(O)<SB>p</SB>; t is 0-2; m is 1-5) or its salt. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

The present invention relates to novel phenylheteroaryls or salts thereof, herbicides containing these as active ingredients, and methods of using the same.

Conventionally, it is known that certain phenylpyrimidine derivatives have herbicidal activity and plant growth regulating action (see, for example, Patent Documents 1 to 10). However, the phenylheteroaryls having a phenyl group, heteroaryl group and amide moiety bonded at specific positions according to the present invention and their herbicidal activity have not been known so far.

European Patent Application Publication No. 354766 European Patent Application No. 425247 Japanese Patent Laid-Open No. 02-275865 U.S. Pat. No. 5,229,915 Japanese Patent Laid-Open No. 03-148264

Japanese Patent Laid-Open No. 02-149466 JP 04-49279 A Japanese Patent Application Laid-Open No. 07-33748 WO99 / 28301 pamphlet JP 05-51369 A

A stable supply of food is indispensable for the resolution of the food crisis accompanying the expected increase in the world population in the near future. The stable supply of food requires economical and efficient killing or control of weeds that hinder cultivation and harvesting, and new herbicides and plant growth regulators will be developed as solutions It has become increasingly important.
An object of the present invention is to provide a novel herbicide having both high safety against crops and excellent herbicidal activity against weeds in order to meet such social demands.

｛式中、Ｒ¹は水素原子、C₁-C₈アルキル基、ハロC₁-C₈アルキル基、C₂-C₈アルケニル基、
C₂-C₈アルキニル基、C₁-C₈アルコキシ基、ハロC₁-C₈アルコキシ基、フェニル基、同一又
は異なっても良く、ハロゲン原子、シアノ基、ニトロ基、水酸基、アミノ基、ＳＨ基、C₁
-C₆アルキル基、ハロC₁-C₆アルキル基、C₂-C₆アルケニル基、ハロC₂-C₆アルケニル基、C₂
-C₆アルキニル基、ハロC₂-C₆アルキニル基、C₁-C₆アルコキシ基、ハロC₁-C₆アルコキシ基
、C₁-C₆アルキルチオ基、ハロC₁-C₆アルキルチオ基、C₂-C₆アルケニルチオ基、ハロC₂-C₆
アルケニルチオ基、C₁-C₆アルキルスルフィニル基、ハロC₁-C₆アルキルスルフィニル基、
C₁-C₆アルキルスルホニル基、ハロC₁-C₆アルキルスルホニル基、C₁-C₆アルキルカルボニ
ル基、ハロC₁-C₆アルキルカルボニル基、フェニルカルボニル基、C₁-C₆アルコキシカルボ
ニル基、モノC₁-C₆アルキルアミノ基又は同一若しくは異なって良いジC₁-C₆アルキルアミ
ノ基から選択される１〜５個の置換基を有する置換フェニル基、 As a result of intensive studies to solve the above problems, the present inventors have found that a compound group having a novel phenylheteroaryl skeleton has excellent herbicidal activity to solve the above problems, and have completed the present invention. It was.
That is, the present invention relates to the general formula (I)

{Wherein R ¹ is a hydrogen atom, a C ₁ -C ₈ alkyl group, a halo C ₁ -C ₈ alkyl group, a C ₂ -C ₈ alkenyl group,
C ₂ -C ₈ alkynyl group, C ₁ -C ₈ alkoxy group, halo C ₁ -C ₈ alkoxy group, phenyl group, may be the same or different, halogen atom, cyano group, nitro group, hydroxyl group, amino group, SH Group, C ₁
-C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₂ -C ₆ alkenyl group, halo C ₂ -C ₆ alkenyl group, C ₂
-C ₆ alkynyl group, halo C ₂ -C ₆ alkynyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C _2- C ₆ alkenylthio group, halo C ₂ -C ₆
Alkenylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group,
C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ alkylcarbonyl group, halo C ₁ -C ₆ alkylcarbonyl group, phenylcarbonyl group, C ₁ -C ₆ alkoxycarbonyl group A substituted phenyl group having 1 to 5 substituents selected from a mono C ₁ -C ₆ alkylamino group or a di C ₁ -C ₆ alkylamino group which may be the same or different;

Phenyl C ₁ -C ₈ alkyl group, which may be the same or different, halogen atom, cyano group, nitro group, hydroxyl group, amino group, SH group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₂ -C ₆ alkenyl group, halo C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, halo C ₂ -C ₆ alkynyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group , C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₂ -C ₆ alkenylthio group, halo C ₂ -C ₆ alkenylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C _1- C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ alkylcarbonyl group, halo C ₁ -C ₆ alkylcarbonyl group, phenylcarbonyl group, C ₁ -C ₆ alkoxycarbonyl group, mono C ₁ -C ₆ alkylamino group or the same or different and may di C ₁ -C ₆ Substituted phenyl C ₁ -C ₈ alkyl radical having from 1 to 5 substituents selected from alkylamino groups on the ring, mono-C ₁ -C ₈ alkylamino group, the same or different and may di C ₁ -C ₈ Alkylamino group, phenylamino group, which may be the same or different, halogen atom, cyano group, nitro group, hydroxyl group, amino group, SH group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C _2- C ₆ alkenyl group, halo C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, halo C ₂ -C ₆ alkynyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C
₁ -C ₆ alkylthio group, C ₂ -C ₆ alkenylthio group, a halo C ₂ -C ₆ alkenylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ An alkylsulfonyl group,
Halo C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ alkylcarbonyl group, halo C ₁ -C ₆ alkylcarbonyl group, phenylcarbonyl group, C ₁ -C ₆ alkoxycarbonyl group, mono C ₁ -C ₆ alkylamino group substituted phenylamino group having from 1 to 5 substituents group or the same or different and are selected from a good-di C ₁ -C ₆ alkylamino group on the ring,

Phenoxy group or same or different, halogen atom, cyano group, nitro group, hydroxyl group, amino group, SH group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₂ -C ₆ alkenyl Group, halo C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, halo C ₂ -C ₆ alkynyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ Alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₂ -C ₆
Alkenylthio group, halo C ₂ -C ₆ alkenylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁
-C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ alkylcarbonyl group, halo C ₁ -C ₆ alkylcarbonyl group, a phenylcarbonyl groups, C ₁ -C ₆ alkoxycarbonyl group, a substituted phenoxy having one to five substituents selected from mono-C ₁ -C ₆ alkylamino group or the same or different and may di C ₁ -C ₆ alkylamino group on the ring Indicates a group.

R ² is a hydrogen atom, C ₁ -C ₈ alkyl group, C ₂ -C ₈ alkenyl group, C ₂ -C ₈ alkynyl group, C ₁ -C ₈ alkoxy C ₁ -C ₈ alkyl group, cyano C ₁ -C ₈ Alkyl group, C ₁ -C ₈ alkylcarbonyl group, halo C
₁ -C ₈ alkylcarbonyl group, C ₂ -C ₈ alkenyl group, a C ₁ -C ₈ alkylsulfonyl group or a halo C ₁ -C ₈ alkylsulfonyl group shown.

R ³ may be the same or different and is a halogen atom, a C ₁ -C ₈ alkyl group, a halo C ₁ -C ₈ alkyl group, a C ₂ -C ₈ alkenyl group, a halo C ₂ -C ₈ alkenyl group, C _2- C ₈ alkynyl group, halo C ₂ -C ₈ alkynyl group, C ₁ -C ₈ alkoxy group, halo C ₁ -C ₈ alkoxy group, C ₁ -C ₈ alkoxy C ₁ -C ₈ alkyl group, halo C ₁ -C ₈ alkoxy C ₁ -C ₈ alkyl group, C ₁ -C ₈ alkoxy C ₁ -C ₈ alkoxy group, halo C ₁
-C ₈ alkoxy C ₁ -C ₈ alkoxy group, C ₁ -C ₈ alkylsulfonyl group, halo C ₁ -C ₈ alkylsulfonyl group, C ₁ -C ₈ alkylthio group, halo C ₁ -C ₈ alkylthio group, C ₁ -C ₈ alkylsulfinyl group, halo C ₁ -C ₈ alkylsulfinyl group, C ₁ -C ₈ alkylsulfonyl group, halo C ₁ -C ₈ alkylsulfonyl group, C ₁ -C ₈ alkylcarbonyl group, C _1- C ₈ alkoxycarbonyl group, C ₁ -C ₈ alkylcarbonyloxy group, halo C ₁ -C ₈ alkylcarbonyloxy group, a hydroxyl group, a formyl group, a cyano group, a nitro group, a trimethylsilyl group, pentafluorosulfur sulfonyl group (-SF ₅ ) Or -C (R ⁴ ) = NOR ⁵ (wherein R ⁴ and R ⁵ may be the same or different and each represents a hydrogen atom, a C ₁ -C ₅ alkyl group or a halo C ₁ -C ₅ alkyl group). ) And two adjacent groups ³ together with each other difluoromethylenedioxy group (-OC
F ₂ O—), a tetrafluoroethylenedioxy group (—OCF ₂ CF ₂ O—), a methylenedioxy group, or an ethylenedioxy group.

G may be the same or different, and —C (═O) —, —C (═S) —, or —C (R ⁶ ) ₂ — (
In the formula, R ⁶ may be the same or different and each represents a hydrogen atom, a cyano group or a C ₁ -C ₈ alkyl group,
And two R ⁶ groups together contain 3-6 carbon atoms, nitrogen atoms, oxygen atoms or sulfur atoms.
Member rings can be formed. )
X represents a single bond, a group represented by —C (═O) —, —C (═S) — or —SOq— (wherein q represents 1 or 2).

Y may be the same or different, and CR ⁷ (wherein R ⁷ is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a carboxyl group, a pentafluorosulfanyl group (-SF ₅ ), C _1-
C ₈ alkyl group, halo C ₁ -C ₈ alkyl group, C ₂ -C ₈ alkenyl group, C ₂ -C ₈ alkynyl group, C ₁ -C ₈ alkoxy group, halo C ₁ -C ₈ alkoxy group, C _1- C ₈ alkoxycarbonyl group, C ₁ -C ₈ alkylthio group, C ₁ -C ₈ alkylsulfinyl group, C ₁ -C ₈ alkylsulfonyl group, C ₁ -C ₈ alkylamino group or di-C ₁ which may be the same or different —C _{8 represents} an alkylamino group. ) Or N → (O
) P (wherein p represents an integer of 0 or 1), and at least two Y are N → (O) p
(Wherein p is the same as above).
t represents an integer of 0 to 2, and m represents an integer of 1 to 5. }, A herbicide containing these as an active ingredient, and a method for using the same.

ADVANTAGE OF THE INVENTION According to this invention, the herbicide which shows the high herbicidal effect and shows sufficient safety | security with respect to an important crop, and the useful compound used for it can be provided.

The present invention will be described in detail below.
In the definition of the phenylheteroaryls or salts thereof represented by the general formula (I) of the present invention, the “halogen atom” refers to a chlorine atom, a bromine atom, an iodine atom or a fluorine atom. "C ₁ -C
“ ₈ alkyl group” means a linear or branched chain or alicyclic alkyl group having 1 to 8 carbon atoms, such as a methyl group, an ethyl group, or a normal propyl group. Group, isopropyl group, cyclopropyl group, 1-methylcyclopropyl group, 2-methylcyclopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group,
Cyclopropylmethyl group, normal pentyl group, neopentyl group, normal hexyl group,
Cyclohexyl group, 1,2,2-trimethylpropyl group, 2-methylcyclopentyl group,
An n-octyl group etc. are mentioned. The “halo C ₁ -C ₈ alkyl group” is a straight chain having 1 to 8 carbon atoms substituted with one or more halogen atoms which may be the same or different, and 3 to 3 carbon atoms.
8 branched or alicyclic alkyl groups, for example, chloromethyl group, 2-chloroethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group 2,2,2-trichloroethyl group, 3-chloropropyl group, 3-bromopropyl group, 3,3,3-trifluoropropyl group, 2,2,3,3-tetrafluoropropyl group, 2,2
, 3,3,3-pentafluoropropyl group, 1-methyl-2,2,2-trifluoroethyl group, 2,2,2-trifluoro-1- (trifluoromethyl) ethyl group, 1-methyl- 2,2,
3,3,3-pentafluoropropyl group, 3-chloropropyl group, 3-bromopropyl group,
4-chlorobutyl group, 4,4,4-trifluorobutyl group, 5,5,5-trifluoropentyl group, 6,6,6-trifluorohexyl group, 7-fluoroheptyl group, 8-chlorooctyl group, 2,2-difluorocyclopropyl group, (2,2-difluorocyclopropyl) methyl group, 2,2-dichlorocyclopropyl group, (2,2-dichlorocyclopropyl)
A methyl group, a perfluorooctyl group, etc. are mentioned. The “C ₂ -C ₈ alkenyl group” refers to a straight chain having 2 to 8 carbon atoms, a branched or alicyclic alkenyl group having 3 to 8 carbon atoms, such as a vinyl group, Allyl group, 2-butenyl group, 2-methyl-2-propenyl group, 1
-Methyl-2-propenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl, 2-pentenyl group, 2-hexenyl group, 2-cyclohexenyl group and the like can be mentioned. "C ₂
The “—C ₈ alkynyl group” means a straight chain having 2 to 8 carbon atoms, a branched or alicyclic alkynyl group having 5 to 8 carbon atoms, such as a propargyl group, 2-butynyl. Group, 1-methyl-2-propynyl group, 2-cyclohexynyl group and the like.

“C ₁ -C ₈ alkoxy group” means a straight-chain alkoxy group having 1 to 8 carbon atoms, 3 carbon atoms
~ 8 branched or alicyclic alkoxy groups, for example, methoxy group, ethoxy group, normal propoxy group, isopropoxy group, cyclopropoxy group, normal butoxy group, secondary butoxy group, tertiary butoxy group, normal Examples include a pentyloxy group, an isopentyloxy group, a neopentyloxy group, a cyclopentyloxy group, a normal hexyloxy group, and a normal octyloxy group. A “halo C ₁ -C ₈ alkoxy group” is a straight-chain alkoxy group having 1 to 8 carbon atoms substituted with one or more halogen atoms which may be the same or different, and a branch having 3 to 8 carbon atoms. Represents a chain or alicyclic alkoxy group, for example,
Chloromethoxy group, fluoromethoxy group, trifluoromethoxy group, 2-chloroethoxy group, 2-fluoroethoxy group, 2,2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2- Trichloroethoxy group, 3-chloropropoxy group, 3-bromopropoxy group, 3,3,3-trifluoropropoxy group, 2,2,3,3-tetrafluoropropoxy group, 2,2,3,3,3- Pentafluoropropoxy group, 2,2-difluorocyclopropoxy group, 2,2-dichlorocyclopropoxy group, 1-methyl-2,2,2-trifluoroethoxy group, 2,2,2-trifluoro-1- ( Trifluoromethyl) ethoxy group, 1-
Methyl-2,2,3,3,3-pentafluoropropoxy group, 3-chloropropoxy group, 3-
Bromopropoxy group, 4-chlorobutoxy group, 4,4,4-trifluorobutoxy group, 5,
5,5-trifluoropentyloxy group, 6,6,6-trifluorohexyloxy group and the like are shown.
Even when these groups represent a moiety as “C ₁ -C ₈ alkyl”, “halo C ₁ -C ₈ alkyl”, etc., the above “C ₁ -C ₈ alkyl group”, “halo C ₁ -C ₈ alkyl group” The same meaning part is shown. Also, “C ₁
“-C ₅ ”, “C ₁ -C ₆ ” and the like indicate a range of carbon numbers such as _{1 to 5} and _{1 to 6} carbon atoms.

In the phenylheteroaryls represented by the general formula (I), R ¹ is preferably C ₁
-C ₈ alkyl group, halo C ₁ -C ₈ alkyl group, C ₂ -C ₈ alkenyl group, halo C ₂ -C ₈ alkenyl group or the same or different, halogen atom, C ₁ -C ₆ alkyl group, A halo C ₁ -C ₆ alkyl group,
A phenyl group having one or more substituents selected from a C ₁ -C ₆ alkoxy group, a halo C ₁ -C ₆ alkoxy group, a cyano group or a nitro group, more preferably a C ₁ -C ₅ alkyl group, A halo C ₁ -C ₅ alkyl group or a phenyl group which may be the same or different and has one or more substituents selected from a halogen atom, a halo C ₁ -C ₅ alkyl group or a halo C ₁ -C ₅ alkoxy group is there.
R ² is preferably a hydrogen atom, C ₁ -C ₈ alkyl group, C ₁ -C ₈ alkoxy C ₁ -C ₈ alkyl group, cyano C ₁ -C ₈ alkyl group, C ₂ -C ₈ alkenyl group, C _2- A C ₈ alkynyl group, a C ₁ -C ₈ alkylcarbonyl group, a halo C ₁ -C ₈ alkylcarbonyl group or a C ₂ -C ₈ alkenylcarbonyl group, more preferably a hydrogen atom, a C ₁ -C ₈ alkyl group or C ₁ -C ₈ alkylcarbonyl group.

R ³ is preferably a C ₁ -C ₈ alkyl group, a halo C ₁ -C ₈ alkyl group, a C ₁ -C ₈ alkoxy C ₁ -C ₈
Alkyl group, halo C ₁ -C ₈ alkoxy C ₁ -C ₈ alkyl group, C ₂ -C ₈ alkenyl group, a halo C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkynyl group, a halo C ₂ -C ₈ alkynyl Group, C ₁ -C ₈ alkoxy group, halo C ₁ -C ₈
Alkoxy group, C ₁ -C ₈ alkoxy C ₁ -C ₈ alkoxy group, halo C ₁ -C ₈ alkoxy C ₁ -C ₈ alkoxy group, pentafluorosulfanyl group (—SF ₅ ), trimethylsilyl group, C ₁ -C ₈ acyloxy group, halo C ₁ -C ₈ acyloxy group, C ₁ -C ₈ alkylsulfonylamino group, halo C ₁ -C ₈ alkylsulfonylamino group, C ₁ -C ₈ alkylcarbonyl group or C ₁ -C ₈ alkoxycarbonyl group More preferably a halo C ₁ -C ₈ alkyl group, a halo C ₁ -C ₈ alkoxy C ₁ -C ₈ alkyl group, a halo C ₁ -C ₈ alkoxy group or a difluoromethylenedioxy group (—OCF ₂ O -).
When Y represents CR ⁷ , R ⁷ is preferably a C ₁ -C ₈ alkyl group, a halo C ₁ -C ₈ alkyl group,
C ₂ -C ₈ alkenyl group, halo C ₂ -C ₈ alkenyl group, C ₂ -C ₈ alkynyl group, halo C ₂ -C ₈ alkynyl group, C ₁ -C ₈ alkoxy group, halo C ₁ -C ₈ alkoxy group , Pentafluorosulfanyl group (-S
F ₅ ), C ₁ -C ₈ alkylthio group, C ₁ -C ₈ alkylsulfinyl group, C ₁ -C ₈ alkylsulfonyl group, mono C ₁ -C ₈ alkylamino group or di-C ₁ -C ₈ alkylamino group Yes, more preferably
A C ₁ -C ₅ alkyl group, a halo C ₁ -C ₅ alkyl group, a C ₁ -C ₅ alkoxy group or a halo C ₁ -C ₅ alkoxy group.

G is preferably a group represented by —C (═O) — or —C (R ⁶ ) ₂ — (wherein R ⁶ is preferably a hydrogen atom or a C ₁ -C ₈ alkyl group). .
X is preferably a single bond or a group represented by —C (═O) —, t is preferably 1, m is preferably 1 or 2, and p is preferably 0.
The salts of phenylheteroaryls represented by the general formula (I) include acetate, propionate, butyrate, oxalate, adipate, dodecanedioate, laurate, stearate, Carboxylates such as fluoroacetate, fumarate, maleate, benzoate, phthalate; methanesulfonate, 1,3-propanedisulfonate, p-toluenesulfonate, dodecylbenzenesulfonic acid Sulfonates such as salts; hydrochlorides, sulfates,
Examples thereof include inorganic acid salts such as nitrate and carbonate.

（式中、Ｒ¹、Ｒ²、Ｒ³、Ｇ、Ｘ、Ｙ、ｔ及びｍは前記に同じくし、ｈａｌはハロゲン原
子を示す。）
一般式（II）で表されるフェニルヘテロアリールアミン類と一般式（III）で表される
酸ハライド類又は一般式（IV）で表される酸無水物類とを不活性溶媒及び塩基の存在下又
は非存在下に反応させることにより本発明の一般式（Ｉ）で表されるフェニルヘテロアリ
ール類を製造することができる。 The phenylheteroaryls of the present invention represented by the general formula (I) are novel compounds and can be produced, for example, according to the following production methods 1 to 10.
Manufacturing method 1

(Wherein R ¹ , R ² , R ³ , G, X, Y, t and m are the same as above, and hal represents a halogen atom.)
Presence of an inert solvent and a base between the phenylheteroarylamine represented by the general formula (II) and the acid halide represented by the general formula (III) or the acid anhydride represented by the general formula (IV) The phenylheteroaryl represented by the general formula (I) of the present invention can be produced by reacting in the absence or absence.

The inert solvent that can be used in this reaction is not particularly limited as long as it does not directly participate in this reaction. For example, aromatic hydrocarbons such as benzene, toluene, and xylene; ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone Halogenated hydrocarbons such as chloroform and dichloromethane; water; esters such as methyl acetate and ethyl acetate; ethers such as diethyl ether, tetrahydrofuran and dioxane; acetonitrile, N, N-dimethylformamide, N-methylpyrrolidone and dimethyl Examples thereof include polar solvents such as sulfoxide and pyridine, and these inert solvents can be used alone or in admixture of two or more.
Examples of the base that can be used in this reaction include alkali metal hydrides such as lithium hydride, sodium hydride and potassium hydride; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide; sodium carbonate, Alkali metal carbonates such as potassium carbonate;
Inorganic salts such as potassium fluoride and cesium fluoride; pyridine, 1,8-diazabicyclo [5
. 4.0] organic bases such as undec-7-ene and triethylamine, and the like, and the amount used is an acid halide represented by the general formula (III) or an acid represented by the general formula (IV) What is necessary is just to perform reaction by selecting suitably in the range of equimolar-excess molar with respect to anhydrides.

Since this reaction is an equimolar reaction, the phenylheteroarylamines represented by the general formula (II) and the acid halides represented by the general formula (III) or the acid anhydrides represented by the general formula (IV) Can be used in an equimolar amount, but any of the reactants can be used in excess, and preferably an acid halide represented by the general formula (III) or an acid anhydride represented by the general formula (IV) It is better to use excessive amounts.
What is necessary is just to select reaction temperature suitably in the range of the boiling point range of -50 degreeC-the inert solvent to be used, Preferably it is the range of 0 degreeC-80 degreeC. The reaction time is not constant depending on the reaction scale and reaction temperature, but is in the range of several minutes to 48 hours.
After the reaction, in order to isolate the phenylheteroaryls represented by the general formula (I) of the present invention as the target product, when using a solvent that dissolves in water, the solvent is distilled off under reduced pressure, , Aromatic hydrocarbons such as benzene, toluene and xylene insoluble in water; halogenated hydrocarbons such as chloroform and dichloromethane; extraction with esters such as ethyl acetate, and acid, base, and saturation as necessary After washing with a saline solution, it is dried with a desiccant such as anhydrous sodium sulfate or anhydrous magnesium sulfate, and the solvent may be distilled off under reduced pressure. When a water-insoluble solvent is used, water is added to the reaction mixture, followed by liquid separation. If necessary, the organic layer is washed with acid, base and saturated brine, and then anhydrous sodium sulfate, anhydrous magnesium sulfate, etc. What is necessary is just to dry with a desiccant and to distill off a solvent under reduced pressure.
Further, if necessary, the residue obtained after distilling off the solvent can be purified by recrystallization, suspension washing, column chromatography or the like.

（式中、Ｒ²、Ｒ³、Ｇ、Ｙ、ｔ及びｍは前記に同じくし、Ｒ⁸はC₁-C₈アルキル基又は置換
されてもよいフェニル基を示し、Ｚは酸素原子又は硫黄原子を示す。）
一般式（II）で表されるフェニルヘテロアリールアミン類と一般式（V）で表されるイ
ソシアナート類又はイソチオシアナート類とを不活性溶媒及び塩基の存在下又は非存在下
に反応させることにより本発明の一般式（Ｉ−１）で表されるフェニルヘテロアリール類
を製造することができる。
本反応は製造方法１に同じくすれば良い。 Manufacturing method 2

Wherein R ² , R ³ , G, Y, t and m are the same as above, R ⁸ is a C ₁ -C ₈ alkyl group or an optionally substituted phenyl group, and Z is an oxygen atom or sulfur. Indicates an atom.)
Reacting the phenylheteroarylamines represented by general formula (II) with the isocyanates or isothiocyanates represented by general formula (V) in the presence or absence of an inert solvent and base. Thus, phenylheteroaryls represented by the general formula (I-1) of the present invention can be produced.
This reaction may be performed in the same manner as in production method 1.

（式中、Ｒ¹、Ｒ²、Ｒ³、Ｇ、Ｙ、ｔ及びｍは前記に同じ。）
一般式（II）で表されるフェニルヘテロアリールアミン類と一般式（VI）で表されるカ
ルボン酸類とを塩基及び縮合剤の存在下、不活性溶媒の存在下又は非存在下に反応させる
ことにより本発明の一般式（Ｉ−２）で表されるフェニルヘテロアリール類を製造するこ
とができる。
本反応で使用できる縮合剤としてはカルボニルジイミダゾール、ジシクロヘキシルカル
ボジイミド、ヨウ化２−クロロ−１−メチルピリジニウム等を挙げることができ、その使
用量は一般に式（VI）で表されるカルボン酸に対して等モル〜過剰モルの範囲で適宜選択
して反応を行えば良い。
本反応は等モル反応であるので一般式（VI）で表されるカルボン酸及び一般式（II）で
表されるフェニルヘテロアリールアミン類を等モル使用すれば良いが、いずれかの反応剤
を過剰に使用することもできる。
本反応で使用できる不活性溶媒、塩基、反応温度、反応時間及び単離方法は製造方法１
に同じくすれば良い。 Manufacturing method 3

(Wherein R ¹ , R ² , R ³ , G, Y, t and m are the same as above)
Reacting phenylheteroarylamines represented by general formula (II) with carboxylic acids represented by general formula (VI) in the presence of a base and a condensing agent in the presence or absence of an inert solvent. Thus, phenylheteroaryls represented by the general formula (I-2) of the present invention can be produced.
Examples of the condensing agent that can be used in this reaction include carbonyldiimidazole, dicyclohexylcarbodiimide, 2-chloro-1-methylpyridinium iodide, and the amount used is generally based on the carboxylic acid represented by the formula (VI). The reaction may be carried out by appropriately selecting in the range of equimolar to excess molar.
Since this reaction is an equimolar reaction, the carboxylic acid represented by the general formula (VI) and the phenylheteroarylamine represented by the general formula (II) may be used in equimolar amounts. It can also be used in excess.
An inert solvent, a base, a reaction temperature, a reaction time, and an isolation method that can be used in this reaction are the production methods 1.
The same as above.

（式中、Ｒ¹、Ｒ²、Ｒ³、Ｙ、ｍ及びｈａｌは前記に同じ。）
一般式（VII）で表されるフェニルヘテロアリールカルボン酸ハライド類と一般式（VII
I）で表されるアミン類とを不活性溶媒及び塩基の存在下又は非存在下に反応させること
により本発明の一般式（Ｉ−３）で表されるフェニルヘテロアリール類を製造することが
できる。
本反応は製造方法１に同じくすれば良い。 Manufacturing method 4

(Wherein R ¹ , R ² , R ³ , Y, m and hal are the same as above)
Phenylheteroarylcarboxylic acid halides represented by general formula (VII) and general formula (VII
The phenylheteroaryls represented by the general formula (I-3) of the present invention can be produced by reacting the amines represented by I) in the presence or absence of an inert solvent and a base. it can.
This reaction may be performed in the same manner as in production method 1.

（式中、Ｒ¹、Ｒ²、Ｒ³、Ｙ及びｍは前記に同じ。）
一般式（VII−1）で表されるフェニルヘテロアリールカルボン酸類と一般式（VIII）で
表されるアミン類とを塩基及び縮合剤の存在下、不活性溶媒の存在下又は非存在下に反応
させることにより一般式（Ｉ−３）で表される化合物を製造することができる。
本反応は製造方法３に同じくすれば良い。 Manufacturing method 5

(In the formula, R ¹ , R ² , R ³ , Y and m are the same as above.)
Reaction of phenylheteroarylcarboxylic acids represented by general formula (VII-1) with amines represented by general formula (VIII) in the presence or absence of an inert solvent in the presence of a base and a condensing agent. By doing so, the compound represented by the general formula (I-3) can be produced.
This reaction may be performed in the same manner as in Production Method 3.

（式中、Ｒ¹、Ｒ²、Ｒ³、Ｇ、Ｘ、Ｙ、ｔ及びｍは前記に同じくし、Wは塩素原子、臭素原
子、ヨウ素原子、メチルスルホニルオキシ基、ｐ−トリルスルホニルオキシ基、トリフル
オロメチルスルホニルオキシ基等の脱離基を示す。）
一般式（IＸ）で表されるヘテロアリール類と一般式（Ｘ）で表されるフェニルボロン
酸類とを塩基及び遷移金属触媒の存在下、配位子又は不活性溶媒の存在下若しくは非存在
下に反応させることにより本発明の一般式（Ｉ）で表されるフェニルヘテロアリール類を
製造することができる。 Manufacturing method 6

(Wherein R ¹ , R ² , R ³ , G, X, Y, t and m are the same as above, W is a chlorine atom, bromine atom, iodine atom, methylsulfonyloxy group, p-tolylsulfonyloxy group) And represents a leaving group such as a trifluoromethylsulfonyloxy group.)
Heteroaryls represented by general formula (IX) and phenylboronic acids represented by general formula (X) in the presence of a base and a transition metal catalyst, in the presence or absence of a ligand or an inert solvent The phenylheteroaryl represented by the general formula (I) of the present invention can be produced by reacting with.

The inert solvent that can be used in this reaction is not particularly limited as long as it does not directly participate in this reaction. For example, alcohols such as methanol, ethanol, isopropyl alcohol;
Aromatic hydrocarbons such as benzene, toluene and xylene; Ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; Halogenated hydrocarbons such as chloroform and dichloromethane; Water; Esters such as methyl acetate and ethyl acetate; Ethers such as tetrahydrofuran and dioxane; acetonitrile, N, N-dimethylformamide,
Examples thereof include polar solvents such as N-methylpyrrolidone, dimethyl sulfoxide, and pyridine. These inert solvents can be used alone or in admixture of two or more.
Examples of the base that can be used in this reaction include alkali metal hydrides such as lithium hydride, sodium hydride and potassium hydride; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide; sodium carbonate Alkali metal carbonates such as potassium carbonate; inorganic salts such as potassium fluoride and cesium fluoride; pyridine, 1,8-diazabicyclo [
5.4.0] organic bases such as undec-7-ene and triethylamine can be mentioned, and the amount used is equimolar to excess molar relative to the phenylboronic acid represented by the general formula (X). The reaction may be carried out by selecting appropriately within the range, preferably 1.5 to 3 times the molar amount.
Transition metal catalysts that can be used in this reaction include palladium on carbon, palladium acetate, dichlorobis (triphenylphosphine) palladium, and tetrakis (triphenylphosphine).
Palladium compounds such as palladium and tris (dibenzylacetone) palladium, bis (
Triphenylphosphine) nickel chloride and tetrakis (triphenylphosphine)
Nickel compounds such as nickel can be used, and the amount used is appropriately selected in the range of 0.0001-fold mol to equimolar with respect to the heteroaryl represented by the general formula (IX). Preferably, it is good to use 0.0001 times mole-0.2 times mole.

As ligands that can be used in this reaction, triphenylphosphine, tri (o-tolyl) phosphine, tri (t-butyl) phosphine, 1,3-bis (diphenylphosphino) propane, 1,4-bis (diphenyl) Phosphine ligands such as phosphino) butane can be used, and the amount used can be appropriately selected in the range of 0.5 to 100 times moles, preferably equimolar to the transition metal catalyst. It is the range of 10 times mole. Moreover, it can also be made to react without using a ligand.
Since this reaction is an equimolar reaction, the heteroaryls represented by the general formula (IX) and the phenylboronic acids represented by the general formula (X) may be used in an equimolar amount. The phenylboronic acid represented by the general formula (X) is preferably used in excess.
The reaction temperature may be appropriately determined within the range of −50 ° C. to the boiling point of the inert solvent used, and is preferably within the range of room temperature to 120 ° C. The reaction time is not constant depending on the reaction scale and reaction temperature, but is in the range of several minutes to 48 hours.
After the reaction, the phenylheteroaryls represented by the general formula (I) of the present invention, which is the target product, can be isolated by the same production method 1.

（式中、Ｒ¹、Ｒ²、Ｒ⁴、Ｒ⁵、Ｇ、Ｘ、Ｙ及びｔは前記に同じ。）
一般式（Ｉ−４）で表されるカルボニル化合物と一般式（ＸI）で表されるオキシアミ
ン類又はその酸付加塩類とを不活性溶媒及び塩基の存在下又は非存在下に反応させること
により本発明の一般式（Ｉ−５）で表されるフェニルアリール類を製造することができる
。 Manufacturing method 7

(Wherein R ¹ , R ² , R ⁴ , R ⁵ , G, X, Y and t are the same as above)
By reacting the carbonyl compound represented by the general formula (I-4) with the oxyamine represented by the general formula (XI) or an acid addition salt thereof in the presence or absence of an inert solvent and a base, The phenylaryl represented by the general formula (I-5) of the invention can be produced.

The inert solvent that can be used in this reaction is not particularly limited as long as it does not directly participate in this reaction. For example, alcohols such as methanol, ethanol, isopropyl alcohol;
Aromatic hydrocarbons such as benzene, toluene and xylene; Halogenated hydrocarbons such as chloroform and dichloromethane; Water; Esters such as methyl acetate and ethyl acetate; Ethers such as diethyl ether, tetrahydrofuran and dioxane; Acetonitrile, N , N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, pyridine, and other polar solvents. These inert solvents can be used alone or in admixture of two or more.
The base that can be used in this reaction may be the same as in Production Method 1.
Since this reaction is an equimolar reaction, an equimolar amount of the carbonyl compound represented by the general formula (I-4) and the oxyamine represented by the general formula (XI) may be used. The oxyamines represented by the general formula (XI) are preferably used in excess.
The reaction temperature may be appropriately determined within the range of −50 ° C. to the boiling point of the inert solvent used, and preferably room temperature to 80 ° C. The reaction time is not constant depending on the reaction scale and reaction temperature,
It ranges from a few minutes to 48 hours.
After the reaction, in order to isolate the phenylaryls represented by the general formula (I-5) of the present invention, which is the target product, the production method 1 may be used.

（式中、Ｒ¹、Ｒ²、Ｒ³、Ｇ、Ｘ、Ｙ，Ｗ、ｔ及びｍは前記に同じ。）
一般式（Ｉ−６）で表されるアミド類と一般式（ＸII）で表される化合物とを不活性溶
媒及び塩基の存在下又は非存在下に反応させることにより本発明の一般式（Ｉ）で表され
るフェニルヘテロアリール類を製造することができる。
本反応は製造方法１に同じくすれば良い。 Manufacturing method 8

(In the formula, R ¹ , R ² , R ³ , G, X, Y, W, t, and m are the same as above.)
By reacting the amide represented by the general formula (I-6) with the compound represented by the general formula (XII) in the presence or absence of an inert solvent and a base, the general formula (I The phenylheteroaryl represented by this can be manufactured.
This reaction may be performed in the same manner as in production method 1.

（式中、Ｒ¹、Ｒ²、Ｒ³、Ｇ、Ｘ、Ｙ、ｔ及びｍは前記に同じくし、Ｙのうち少なくとも
１つはＮ→Ｏを示し、Ｙ’は窒素原子又はＣ−Ｒ⁷（式中、Ｒ⁷は前記に同じ。）を示し、
少なくとも２つのＹ’は窒素原子を示す。）
一般式（Ｉ−７）で表されるフェニルヘテロアリール類と酸化剤とを不活性溶媒存在下
又は非存在下に反応させることにより一般式（Ｉ−８）で表されるフェニルヘテロアリー
ル−Ｎ−オキシド類を製造することができる。 Manufacturing method 9

(Wherein R ¹ , R ² , R ³ , G, X, Y, t and m are the same as above, at least one of Y represents N → O, and Y ′ represents a nitrogen atom or C—R. ⁷ wherein R ⁷ is as defined above,
At least two Y ′ represent a nitrogen atom. )
The phenylheteroaryl-N represented by the general formula (I-8) is reacted with the phenylheteroaryl represented by the general formula (I-7) and an oxidizing agent in the presence or absence of an inert solvent. -Oxides can be produced.

The inert solvent that can be used in this reaction is not particularly limited as long as it does not directly participate in this reaction. For example, aromatic hydrocarbons such as benzene, toluene, and xylene; ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone Halogenated hydrocarbons such as chloroform and dichloromethane; water; esters such as methyl acetate and ethyl acetate; organic acids such as formic acid, acetic acid and trifluoroacetic acid; acetonitrile, N, N-dimethylformamide, N-methylpyrrolidone and the like These inert solvents can be used alone or in admixture of two or more.
Examples of the oxidizing agent that can be used in this reaction include m-chlorobenzoic acid, hydrogen peroxide, and peracetic acid.
Since this reaction is an equimolar reaction, the phenylheteroaryls represented by the general formula (I-7) and the oxidizing agent may be used in equimolar amounts, but any of the reactants can be used in excess.
It is preferable to use an oxidizing agent in excess.
The reaction temperature may be appropriately determined in the range of −50 ° C. to the boiling point range of the inert solvent used, and is preferably in the range of 0 ° C. to 25 ° C. The reaction time is not constant depending on the reaction scale and reaction temperature,
It ranges from a few minutes to 48 hours.
After the reaction, in order to isolate the heteroaryl-N-oxides represented by the general formula (I-8) as the target product, the production method 1 may be used.

（式中、Ｒ¹、Ｒ²、Ｒ³、Ｇ、Ｘ、Ｙ、ｔ及びｍは前記に同じくし、Ａは酸を示す。）
一般式（Ｉ）で表されるフェニルヘテロアリール類と酸類とを不活性溶媒存在下又は非
存在下に反応させることにより本発明の一般式（Ｉ−９）で表される酸付加塩類を製造す
ることができる。 Manufacturing method 10

(In the formula, R ¹ , R ² , R ³ , G, X, Y, t and m are the same as above, and A represents an acid.)
An acid addition salt represented by the general formula (I-9) of the present invention is produced by reacting a phenylheteroaryl represented by the general formula (I) with an acid in the presence or absence of an inert solvent. can do.

As the acid that can be used in this reaction, an organic acid or an inorganic acid can be used. As the organic acid, acetic acid, propionic acid, butyric acid, oxalic acid, adipic acid, dodecanedioic acid, lauric acid, stearic acid, trifluoroacetic acid, Examples thereof include carboxylic acids such as fumaric acid, maleic acid, benzoic acid and phthalic acid; sulfonic acids such as methanesulfonic acid, 1,3-propanedisulfonic acid, p-toluenesulfonic acid and dodecylbenzenesulfonic acid. Examples of inorganic acids include hydrochloric acid, sulfuric acid, nitric acid, carbonic acid and the like.
The inert solvent that can be used in this reaction is not particularly limited as long as it does not directly participate in this reaction. For example, aromatic hydrocarbons such as benzene, toluene, and xylene; ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone Halogenated hydrocarbons such as chloroform and dichloromethane; water; esters such as ethyl acetate and methyl acetate; polar solvents such as tetrahydrofuran, acetonitrile, dioxane, N, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide; Can be mentioned.
Since this reaction is an equimolar reaction, it is sufficient to use equimolar amounts of the phenylheteroaryls and acids represented by the general formula (I), but any of the reactants can be used in excess, preferably acids. Should be used in excess.
The reaction temperature may be appropriately determined within the range of −50 ° C. to the boiling point of the inert solvent to be used, preferably 0 ° C. to 25 ° C. The reaction time is not constant depending on the reaction scale and reaction temperature,
It ranges from a few minutes to 48 hours.
After the reaction, the acid addition salt of phenylheteroaryls represented by the general formula (I-9), which is the target product, can be isolated by distilling off the solvent under reduced pressure and filtering the precipitated crystals. Although it may be a sufficiently pure product as it is, it can be purified by washing with the above inert solvent, if necessary.

（式中、Ｒ³、Ｙ、Ｗ及びｍは前記に同じ。）
製造方法１、２及び３の中間体である一般式（II）で表されるフェニルヘテロアリール
アミン類のうち一般式（II−３）で表されるフェニルヘテロアリールアミン類は、一般式
（ＸIII）で表されるシアノヘテロアリール類と一般式（Ｘ）で表されるフェニルボロン
酸類とを塩基及び遷移金属触媒の存在下、配位子又は不活性溶媒の存在下若しくは非存在
下に反応させることにより一般式（ＸＩＶ）で表されるフェニルシアノヘテロアリール類
とし、該フェニルシアノヘテロアリール類（ＸＩＶ）を単離し又は単離せずして、不活性
溶媒の存在下又は非存在下に還元することにより製造することができる。
また、一般式（ＸＩＶ）で表されるフェニルシアノヘテロアリール類はＪ．Ｍｅｄ．Ｃ
ｈｅｍ．，３６，４６−５４（１９９３）記載の方法に準じても製造できる。
出発原料である一般式（ＸIII）で表されるシアノヘテロアリール類は特開昭６０−１
８５７６４号公報又はＴｅｔｒａｈｅｄｒｏｎ，４１，４９４１（１９８５）記載の方法
に準じて製造できる。 The intermediate described in the above production example can be produced by the intermediate production method shown below.
Intermediate production method 1

(Wherein R ³ , Y, W and m are the same as above)
Among the phenylheteroarylamines represented by the general formula (II) which are intermediates of the production methods 1, 2 and 3, the phenylheteroarylamines represented by the general formula (II-3) are represented by the general formula (XIII ) And a phenylboronic acid represented by the general formula (X) are reacted in the presence of a base and a transition metal catalyst in the presence or absence of a ligand or an inert solvent. To phenylcyanoheteroaryls represented by general formula (XIV), and the phenylcyanoheteroaryls (XIV) are reduced in the presence or absence of an inert solvent, with or without isolation. Can be manufactured.
In addition, phenylcyanoheteroaryls represented by the general formula (XIV) are described in J. Org. Med. C
hem. 36, 46-54 (1993).
Cyanoheteroaryls represented by general formula (XIII) as starting materials are disclosed in JP-A-60-1
No. 85764 or Tetrahedron, 41 , 4941 (1985).

1-1) General formula (XIII) → General formula (XIV)
This reaction may be performed in the same manner as in production method 6.
1-2) General formula (XIV) → General formula (II-3)
This reaction is well known in the literature (for example, the Chemical Society of Japan, “New Experimental Chemistry Course”, Volume 20, p. 27).
9, 1977, see Maruzen Co., Ltd. The preferred reduction method includes, for example, a method using a metal hydride such as sodium borohydride or lithium aluminum hydride as a reducing agent, catalytic hydrogenation with a metal catalyst and hydrogen, etc. Can be mentioned.
When a metal hydride is used as the reducing agent, this reaction is a stoichiometric reaction, and therefore the general formula (X
The metal hydride may be used in a stoichiometric amount with respect to the phenylcyanoheteroaryls represented by III), but it is preferable to use an excess of the metal hydride. Reaction temperature is -100
It may be appropriately performed within the range of from ° C to the boiling point of the inert solvent, and preferably from -78 ° C to room temperature. The reaction time is not constant depending on the reaction scale and reaction temperature, but is in the range of several minutes to 48 hours.
In the case of catalytic hydrogenation with a metal catalyst and hydrogen, examples of the metal catalyst include Raney nickel, palladium carbon, platinum oxide and the like.

The reaction temperature may be appropriately determined within the range of room temperature to the boiling point of the inert solvent used, and is preferably within the range of room temperature to 50 ° C. The hydrogen pressure may be performed as appropriate in the range of normal pressure ~100Kgf / cm ^2, and preferably range of normal pressure ~10Kgf / cm ^2. The reaction time is not constant depending on the reaction scale, temperature and pressure, but is in the range of several minutes to 48 hours. Further, as described in the above literature, additives such as acids and bases can be added for the purpose of improving the reaction rate and suppressing by-products.
The solvent is not particularly limited as long as it does not directly participate in this reaction. For example, alcohols such as methanol, ethanol and isopropyl alcohol; aromatic hydrocarbons such as benzene, toluene and xylene; acetone, methyl ethyl ketone and methyl isobutyl ketone Ketones such as; halogenated hydrocarbons such as chloroform and dichloromethane; water; methyl acetate,
Esters such as ethyl acetate; tetrahydrofuran, acetonitrile, dioxane, N, N
Examples thereof include polar solvents such as dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, and pyridine, and these inert solvents can be used alone or in admixture of two or more.
After the reaction, in order to isolate the phenylheteroarylamines represented by the general formula (II-3) as the target product, after treating the remaining metal hydrogen compound or filtering the metal catalyst, the solvent is removed under reduced pressure. It may be distilled off. Although it may be a sufficiently pure product as it is, it can be purified by means such as distillation or column chromatography, if necessary.

（式中、Ｒ³、Ｒ⁶、Ｙ及びｍは前記に同じくし、Ｒ⁹は水素原子又はC₁-C₆アルキル基を示
す。）
製造方法１、２及び３の中間体である一般式（II）で表されるフェニルヘテロアリール
アミン類のうち一般式（II−４）で表されるフェニルヘテロアリールアミン類は一般式（
ＸＶ）で表されるオキシム類を不活性溶媒の存在下又は非存在下に還元することにより製
造することができる。
本反応は中間体製造方法１に同じくすれば良い。
原料である一般式（ＸＶ）で表されるオキシム類は製造方法７に準じて製造できる。 Intermediate production method 2

(In the formula, R ³ , R ⁶ , Y and m are the same as described above, and R ⁹ represents a hydrogen atom or a C ₁ -C ₆ alkyl group.)
Among the phenylheteroarylamines represented by the general formula (II) which are intermediates of the production methods 1, 2 and 3, the phenylheteroarylamines represented by the general formula (II-4) are represented by the general formula (II).
XV) can be produced by reducing in the presence or absence of an inert solvent.
This reaction may be performed in the same manner as in Intermediate production method 1.
The oxime represented by the general formula (XV) as a raw material can be produced according to Production Method 7.

（式中、Ｒ³、Ｙ、ｈａｌ及びｍは前記に同じ。）
製造方法５の中間体である一般式（ＶII−１）で表されるフェニルへテロアリールカル
ボン酸類は、一般式（ＸIＶ）で表されるフェニルシアノヘテロアリール類を不活性溶媒
の存在下又は非存在下に加水分解することにより製造することができる。更に該フェニル
ヘテロアリールカルボン酸類（ＶII−１）を単離し又は単離せずして、不活性溶媒の存在
下又は非存在下にハロゲン化することにより製造方法４の中間体である一般式（ＶII）で
表されるフェニルへテロアリールカルボン酸ハライド類を製造することができる。 Intermediate production method 3

(In the formula, R ³ , Y, hal and m are the same as above.)
The phenylheteroarylcarboxylic acids represented by the general formula (VII-1), which is an intermediate of the production method 5, are substituted with phenylcyanoheteroaryls represented by the general formula (XIV) in the presence or absence of an inert solvent. It can be produced by hydrolysis in the presence. Furthermore, the phenylheteroarylcarboxylic acid (VII-1) is isolated or not isolated, and is halogenated in the presence or absence of an inert solvent to give an intermediate of the general formula (VII) ) Can be produced.

3-1) General formula (XIV) → General formula (VII-1)
This reaction is well known in the literature (for example, the Chemical Society of Japan, “New Experimental Chemistry Course”, Vol. 22, p. 12).
1977, see Maruzen Co., Ltd. ) Can be carried out according to the method described.
3-2) General formula (VII-1) → General formula (VII)
This reaction is well known in the literature (for example, the Chemical Society of Japan, “New Experimental Chemistry Course”, Vol. 14, p. 11).
See Maruzen, 06, 1977. ) Can be carried out according to the method described.

（式中、Ｒ¹、Ｒ²、Ｒ⁸、Ｇ、Ｘ、Ｙ、Ｗ、Ｚ及びｔは前記に同じ。）
製造方法６の中間体である一般式（IＸ）で表されるヘテロアリール類は、一般式（Ｘ
ＶＩ）で表されるアミン類と一般式（III）で表される酸ハライド類又は一般式（IV）で
表される酸無水物類とを不活性溶媒及び塩基の存在下又は非存在下に反応させることによ
りを製造することができる。 Intermediate production method 6

(Wherein R ¹ , R ² , R ⁸ , G, X, Y, W, Z and t are the same as above)
Heteroaryls represented by general formula (IX), which are intermediates in production method 6, are represented by general formula (X
VI) and the acid halides represented by the general formula (III) or the acid anhydrides represented by the general formula (IV) in the presence or absence of an inert solvent and a base. It can be manufactured by reacting.

Of the heteroaryls represented by the general formula (IX), the heteroaryls represented by the general formula (IX-1) are the amines represented by the general formula (XVI) and the general formula (V). It can be produced by reacting the represented isocyanates or isothiocyanates in the presence or absence of an inert solvent and a base.
6-1) General formula (XVI) → General formula (IX)
This reaction may be performed in the same manner as in production method 1.
6-2) General formula (XVI) → General formula (IX-1)
This reaction may be performed in the same manner as in production method 2.

（式中、Ｒ¹、Ｒ²、Ｙ、Ｗ及びｈａｌは前記に同じ。）
一般式（IＸ）で表されるヘテロアリール類のうち一般式（IＸ−２）で表されるヘテロ
アリール類は、一般式（V）で表されるアミン類と一般式（ＸＶII）で表されるカルボン
酸類又は一般式（XVIII）で表される酸ハライド類とを不活性溶媒及び塩基の存在下又は
非存在下に反応させることにより製造することができる。
本反応は製造方法４及び５に同じくすれば良い。 Intermediate production method 7

(Wherein R ¹ , R ² , Y, W and hal are the same as above.)
Among the heteroaryls represented by the general formula (IX), the heteroaryls represented by the general formula (IX-2) are represented by the amines represented by the general formula (V) and the general formula (XVII). Can be produced by reacting a carboxylic acid or an acid halide represented by the general formula (XVIII) in the presence or absence of an inert solvent and a base.
This reaction may be carried out in the same manner as in production methods 4 and 5.

The compounds of the present invention and intermediates thereof that can be produced by the above production method are shown in Tables 1 to 6.
Although illustrated in the table, the present invention is not limited to these. In the table, “n-” is normal, “s- is secondary”, “i-” is iso, “c-” is cyclo, “t-”
Indicates tertiary, and “-” indicates no substitution. In addition, Compound No. “*” Appended to indicates that it is a hydrochloride.

When the phenylheteroaryls represented by the general formula (I) of the present invention or salts thereof are used as herbicides, they are generally formulated and used in a convenient form in accordance with conventional methods for agricultural chemical formulations. Is. That is, the phenylheteroaryls or salts thereof represented by the general formula (I) of the present invention are blended in a suitable ratio together with a suitable inert carrier or, if necessary, an auxiliary agent. Dissolve, separate, suspend, mix, impregnate, adsorb or adhere, appropriate dosage form such as suspension, milk suspension, emulsion, liquid, wettable powder, granule, powder, tablet, jumbo, pack What is necessary is just to formulate and use for a medicine etc.
The inert carrier that can be used in the present invention may be either solid or liquid. Examples of materials that can be used as a solid carrier include vegetable powders (for example, soybean flour, cereal flour, wood flour, bark flour, Sawdust, tobacco stem powder, walnut shell powder, bran, fiber powder, residue after extraction of plant extracts, etc.)
, Synthetic polymers such as pulverized synthetic resins, clays (eg kaolin, bentonite, acid clay)
Talc {eg, talc, pyrophyllite, etc.), silica (eg diatomaceous earth, silica sand, mica, white carbon (synthetic, highly dispersed silicic acid, also called hydrous fine silicon, hydrous silicic acid, and some products contain calcium silicate as the main component) )), Activated carbon, natural minerals (eg sulfur powder, pumice, calcined diatomaceous earth, attapulgite and zeolite), calcined diatomaceous earth, brick ground, fly ash, sand, plastic carrier, etc. (eg polyethylene, polypropylene, polyvinylidene chloride) Etc.), inorganic mineral powders such as calcium carbonate and calcium phosphate, chemical fertilizers such as ammonium sulfate, phosphorous acid, ammonium nitrate, urea, and ammonium sulfate, compost, etc., which are used alone or in a mixture of two or more. Used in form.

The material that can be used as a liquid carrier is selected from those having solvent ability itself and those capable of dispersing the active ingredient compound with the aid of an auxiliary agent without having solvent ability.
For example, the following carriers can be exemplified as typical examples, and these are used alone or in the form of a mixture of two or more thereof, for example, water, alcohols (for example, methanol, ethanol, isopropyl alcohol, butanol, ethylene glycol, etc.), Ketones (eg, acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.), ethers (eg, ethyl ether, dioxane, cellosolve, dipropyl ether, tetrahydrofuran, etc.), aliphatic hydrocarbons (eg, kerosene, Mineral oil etc.), aromatic hydrocarbons (eg benzene, toluene, xylene, solvent naphtha, alkylnaphthalene etc.), halogenated hydrocarbons (eg dichloroethane, chloroform, carbon tetrachloride etc.), esters (eg acetic acid) Chill, di isopropoxy pills phthalate, dibutyl phthalate, dioctyl phthalate), amides (e.g. dimethylformamide, diethylformamide, dimethylacetamide), nitriles (e.g., acetonitrile, etc.), and the like dimethyl sulfoxides.
As other adjuvants, the following typical adjuvants can be mentioned, and these adjuvants are used depending on the purpose and are used alone, or in some cases, two or more kinds of adjuvants are used together. In some cases it is possible to use no adjuvants at all. Surfactants are used for the purpose of emulsifying, dispersing, solubilizing and / or wetting of the active ingredient compound, such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene higher fatty acid ester, polyoxyethylene. Examples of surfactants such as resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylaryl sulfonate, naphthalene sulfonate condensate, lignin sulfonate, higher alcohol sulfate Can do.

In addition, for the purpose of stabilizing the dispersion of the active ingredient compound, adhesion and / or binding, the following auxiliary agents can be used, for example, casein, gelatin, starch, methylcellulose, carboxymethylcellulose, gum arabic, polyvinyl Adjuvants such as alcohol, pine oil, coconut oil, bentonite and lignin sulfonate can also be used. In order to improve the fluidity of solid products, the following adjuvants may be used, and for example, adjuvants such as waxes, stearates and alkyl phosphates may be used. As a peptizer for the suspension product, for example, auxiliary agents such as naphthalenesulfonic acid condensate and condensed phosphate can be used. As the antifoaming agent, for example, an auxiliary agent such as silicone oil can be used.
The blending ratio of the active ingredient compound can be adjusted as necessary and is not particularly limited, but the lower limit is about 0.001% by weight to the upper limit is about 90% by weight. For example, the lower limit of the powder or granule is preferably about 0.01% by weight, more preferably about 0.1% by weight,
The upper limit is preferably about 50% by weight, more preferably about 10% by weight, and the lower limit in the case of using an emulsion, wettable powder or granulated wettable powder is preferably about 0.01% by weight, more preferably about 0.1% by weight. About 1% by weight and the upper limit is preferably about 90% by weight, more preferably about 60% by weight.

In the case of applying a preparation containing phenylheteroaryls represented by the general formula (I) or salts thereof of the present invention diluted with water, in order to improve adhesion and spreadability, and to increase the herbicidal effect Adjuvants such as spreading agents may be added to the spray liquid. Adjuvants such as spreading agents used include surfactants (the above-mentioned nonionic surfactants, cationic surfactants, anionic surfactants, amphoteric surfactants), paraffin, and polyvinyl acetate. , Polyacrylate, ethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, crop oil (mineral oil, animal and vegetable oil, etc.), liquid fertilizer and the like. Two or more of these adjuvants may be used simultaneously as necessary. The amount of auxiliary agent such as a spreading agent varies depending on the type, but it is usually appropriate to add 0.01 to 5% by weight in the spray liquid. Moreover, depending on the kind of adjuvant, it is also possible to add beforehand as a component in a formulation.
The application rate of the herbicide containing the phenylheteroaryls represented by the general formula (I) of the present invention or a salt thereof as an active ingredient depends on conditions such as the structure of the compound, the target weeds, the treatment time, the treatment method, and the properties of the soil. Usually, the amount of active ingredient per hectare is 2 to 2000 g,
A range of 5 to 1000 g is preferable.

As the target weeds of the herbicide of the present invention, in the field, for example, Shiroza, Akaza, Inuta, Harutade, Inubiyu, Aobayu, Jacobe, Photonosa, Ichibi, Onamomi, Marubaasagao, Datura, Prunus cinerea, Yamgra, Seiyo Sumire , Broad-leaved weeds such as Aroshagiku and Kosendangusa, and narrow-leaved weeds such as barnyard grass, barnyard grass, barnyardgrass, and sorghum. In paddy fields, for example, broad-leaved weeds such as kikashigusa, azena, konagi, abnomome, mizojakobe, heramodaka, omodaka, urikawa, and narrow-leaved weeds such as Tainubie, Tamagayatsu, Inuta firefly, and Mitsugayatsuri.
The herbicide of the present invention can control the above weeds in field and paddy fields by any of the soil treatment, foliage treatment, and flooding treatment methods. The herbicide of the present invention is
For example, cultivated crops including corn, wheat, barley, rice, soybean and other crops with improved genetic traits and imparted drug resistance have little effect in both soil treatment and foliage treatment. Can be used as a selective herbicide.
The herbicides of the present invention include other pesticides such as insecticides, fungicides, plant growth regulators used in the same field,
And mixed with fertilizer. In addition, in order to further stabilize the herbicidal effect, it can be mixed with other herbicides. When the phenylheteroaryls represented by the general formula (I) of the present invention or salts thereof and other herbicides are mixed and applied, both preparations may be mixed at the time of application, but both are included in advance. It may be applied as a preparation. Examples of herbicides that can be suitably mixed and applied for the above purpose include the following.

Glyphosate and salts thereof, glyphosate and salts thereof, bialaphos and salts thereof, butaphos, anilophos, organophosphorus herbicides such as benzulide, sulfate, dialate, trialate, EPTC, butyrate, esprocarb, thiobencarb (benchocarb), molinate, isopolynate, Carbamate herbicides such as dimethylpiperate, piributicalbu, fenmedifam, chlorprofam, ashram, diuron, linuron,
Urea herbicides such as fluometuron, diphenoxuron, diemron, isoproturon, isouron, tebuthiuron, metabenzthiazurone, metbenzuron, chlorotoluron,
Metazachlor, alachlor, butachlor, pretilachlor, acetochlor, metolachlor, tenyl chlor, diethyl, dimethenamide, propanyl, diflufenican, mefenacet, flufenacet, bromobutide, isoxaben (benzamizole) amide herbicide, trifluralin, benfluralin, pro Dinitroaniline herbicides such as diamine, oryzalin, butralin, pendimethalin,

2,4-D and derivatives thereof, 2,4,5-T and derivatives thereof, MCPA and derivatives thereof,
Dicloprop and derivatives thereof, mecoprop and derivatives thereof, MCPB and derivatives thereof, dicamba and derivatives thereof, 2,3,6-TBA and derivatives thereof, quinclolac and derivatives thereof, quinmelac and derivatives thereof, clopyralide and derivatives thereof, picloram And its derivatives, triclopyr and its derivatives, fluroxypyr and its derivatives, benazoline and its derivatives, diclohop and its derivatives, fluazifop and its derivatives, haloxyhop and its derivatives, phenoxaprop and its derivatives, quizalofop and its derivatives, clodinahop and its derivatives , Carboxylic acid herbicides such as cyhalohop and its derivatives, bromoxynil and its derivatives, ioxynil and its derivatives, phenolic such as dinoterb and its derivatives Herbicide, alloxydim and salts thereof, sethoxydim, cycloxydim, tralkoxydim, Butorokishijimu, clethodim, tepraloxydim, sulcotrione, mesotrione, cyclohexanedione herbicides such as benzobicyclon,

Diphenyl ether herbicides such as chloronitrophene, chloromethoxynyl, oxyfluorfen, biphenox, acifluorfen and salts thereof, fluoroglycophene, lactofen, fomesafen, acloniphen, amidosulfuron, chlorimuron ethyl,
Sulfomelone methyl, primissulfuron, bensulfuron methyl, ethoxysulfuron, cyclosulfamuron, chlorsulfuron, metsulfuron methyl, tribenuron methyl, triasulfuron, sinosulfuron, etamethsulfuron methyl, triflusulfuron methyl , Prosulfuron, thifensulfuron methyl, pyrazosulfuron ethyl, halosulfuron methyl, furazasulfuron, rimsulfuron, nicosulfuron, flupirsulfuron and its salts, imazosulfuron, sulfosulfuron, iodosulfuron, tritosulfuron, mesosulfuron Sulfonylurea herbicides such as paraquat, diquat and other pyridinium herbicides, pyrazolate herbicides such as pyrazolate, pyrazoxifene and benzophenap, simazine Atrazine, cyanazine, simetryn, dimethametryn,
Triazifram, triazine herbicides such as metribudine, imazametabenz, imazapyr and salts thereof, imazaquin and salts thereof, imazetapyr and salts thereof, imazamox and salts thereof, imidazolinone herbicides,

Other herbicides include indanophan, fluridone, flurochloridone, flurtamone, norflurazon, fenfentrol, fentrazamide, sulfentrazone, carfentrazone ethyl, pentoxazone, oxadiazone, oxadialgyl, pyraflufenethyl, isopropazole, flupoxam, Chromazone, isoxaflutol, isoxachlortol, dithiopyr, thiazopyr, pyrithiobac and salts thereof, pyriminobacmethyl, bispyribac and salts thereof, bromacil, terbacil, lenacyl, flupropacil, oxadichromemephone, cinmethyline, chlorphthalim, full microlacpentyl, Flumioxazin, sinidone ethyl, azaphenidine, fluthiaset methyl, flumethram, metoslam, black Nsuramumechiru, benfuresate, ethofumesate, bentazone, pyraclonil, Befurubutamido, picolinafen, florasulam, propoxy carbazone, Furukarubazon and its salts, Shinidon'echiru, Pinokisaben and the like.

Hereinafter, the present invention will be described more specifically with reference to Examples, Formulation Examples, and Test Examples, but the present invention is not limited to these unless it exceeds the gist.
Example 1 Preparation of N-{[4-methyl-6- (3-trifluoromethoxyphenyl) -pyrimidin-2-yl] methyl} cyclopropanecarboxamide (Compound No. 1-3) [4-Methyl-6 (3-Trifluoromethoxyphenyl) -pyrimidin-2-yl]
Methylamine (0.3 g, 1.1 mmol) and triethylamine (0.5 ml, 3.6
(Mmol) of ethyl acetate (20 ml) was cooled to 0 to 4 ° C., and a solution of cyclopropanecarbonyl chloride (0.12 g, 1.1 mmol) in ethyl acetate (5 ml) was added with stirring, followed by stirring for 30 minutes. did. Water (20 ml) was added to the reaction mixture, extracted with ethyl acetate, washed with dilute hydrochloric acid, water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the precipitated crystals were washed with hexane to obtain 0.31 g of the desired product.
Yield: 83%
Physical property: Melting point 136-137 ° C

Example 2 N- (4-Fluorophenyl) -4- (4-trifluoromethoxyphenyl)
Preparation of pyrimidine-2-carboxamide (Compound No. 2-1) 4- (4-trifluoromethoxyphenyl) pyrimidine-2-carboxylic acid (0.15 g
, 0.5 mmol), 4-fluoroaniline (0.06 g, 0.5 mmol) and 2-chloro-1-methylpyridinium iodide (0.30 g, 1.17 mmol) in tetrahydrofuran (5 ml) in triethylamine. (0.5 ml, 3.6 mmol) was added and stirred at room temperature for 1 day. Water (20 ml) was added to the reaction mixture, extracted with ethyl acetate, washed with dilute hydrochloric acid, water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography to obtain 0.04 g of the desired product.
Yield: 21%
Physical property: Melting point 120-121 ° C

Although the typical formulation example and test example of this invention are shown below, this invention is not limited to these. In the preparation examples, “parts” means “parts by weight”.
Formulation Example 1
Compound of the present invention 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts A mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts or more are uniformly mixed and dissolved to prepare an emulsion.
Formulation Example 2
Compound of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts or more is mixed and ground uniformly to form a powder.

Formulation Example 3
Compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts 5 parts or more of calcium lignin sulfonate are uniformly mixed, kneaded with an appropriate amount of water, granulated and dried to give granules.
Formulation Example 4
20 parts of the compound of the present invention
Kaolin and synthetic highly dispersed silicic acid 75 parts
A mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 5 parts or more is uniformly mixed and ground to obtain a wettable powder.

Test Example 1 Herbicidal effect test on paddy weeds before emergence 75 cm ² plastic pot is filled with soil (soil loam soil), seeds of firefly, which is paddy field weeds, are seeded and mixed with seeds of kogi, azena and mizojakobe 75 cm After covering with ³ , the water was submerged to a depth of 5 cm. On the next day, a predetermined effective dose (ga.i./ha) of a drug containing the compound of the present invention prepared according to Formulation Examples 1 to 4 as an active ingredient was diluted with water and subjected to a dripping treatment on the water surface. Subsequently, it was grown in a greenhouse, and the herbicidal effect was investigated 28 days after the treatment, and the herbicidal effect was evaluated in comparison with no treatment.
As a result, Example No. Compound No. 1-1, 1-3, 1-4, 1-5, 1-6, 1-7, 1
-8, 1-56, 1-57, 1-58 is 1000 ga.i./h for any of the above grass species
The control effect of 90% or more was shown by a.

Test Example 2 Herbicidal effect test on paddy weeds after emergence.
75cm ² plastic pot is filled with soil (soil loam), seeds of Inobie and firefly, which are paddy field weeds, are seeded with seeds of kogi, azena and mizojakobe 75cm
After covering with ³ , the water was submerged to a depth of 5 cm and grown in a greenhouse. When the test plant was in the first leaf stage, a drug containing the compound of the present invention as an active ingredient was treated as a chemical solution having a predetermined effective dose (ga.i./ha). Subsequently, it was grown in a greenhouse, and the herbicidal effect was investigated 28 days after the treatment, and the herbicidal effect was evaluated in comparison with no treatment.
As a result, Example No. Compound No. 1-1, 1-3, 1-4, 1-5, 1-6, 1-7, 1
-8, 1-56, 1-57, 1-58 is 1000 ga.i./h for any of the above grass species
The control effect of 90% or more was shown by a.

Claims (6)

Formula (I)

{Wherein R ¹ is a hydrogen atom, a C ₁ -C ₈ alkyl group, a halo C ₁ -C ₈ alkyl group, a C ₂ -C ₈ alkenyl group,
C ₂ -C ₈ alkynyl group, C ₁ -C ₈ alkoxy group, halo C ₁ -C ₈ alkoxy group, phenyl group, may be the same or different, halogen atom, cyano group, nitro group, hydroxyl group, amino group, SH Group, C ₁
-C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₂ -C ₆ alkenyl group, halo C ₂ -C ₆ alkenyl group, C ₂
-C ₆ alkynyl group, halo C ₂ -C ₆ alkynyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C _2- C ₆ alkenylthio group, halo C ₂ -C ₆
Alkenylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group,
C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ alkylcarbonyl group, halo C ₁ -C ₆ alkylcarbonyl group, phenylcarbonyl group, C ₁ -C ₆ alkoxycarbonyl group a substituted phenyl group having from 1 to 5 substituents selected from mono C ₁ -C ₆ alkylamino group or the same or different and may di C ₁ -C ₆ alkylamino group, a phenyl C ₁ -C ₈ alkyl group , Which may be the same or different, halogen atom, cyano group, nitro group, hydroxyl group, amino group,
SH group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₂ -C ₆ alkenyl group, halo C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, halo C ₂ -C ₆ alkynyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₂ -C ₆ alkenylthio group, halo C ₂ -C ₆ alkenylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ An alkylcarbonyl group, a halo C ₁ -C ₆ alkylcarbonyl group, a phenylcarbonyl group, a C ₁ -C ₆ alkoxycarbonyl group, a mono C ₁ -C ₆ alkylamino group or the same or different di-C ₁ -C ₆
A substituted phenyl C ₁ -C ₈ alkyl group, mono C ₁ -C ₈ alkylamino group, di-C ₁ -C which may be the same or different, each having 1 to 5 substituents selected from alkylamino groups on the ring ₈ alkylamino group, phenylamino group, which may be the same or different, halogen atom, cyano group, nitro group,
Hydroxyl group, amino group, SH group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₂ -C ₆ alkenyl group, halo C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, Halo C ₂ -C ₆ alkynyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C _2-
C ₆ alkenylthio group, halo C ₂ -C ₆ alkenylthio group, C ₁ -C ₆ alkylsulfinyl group, halo
C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ alkylcarbonyl group, halo C ₁ -C ₆ alkylcarbonyl group, phenylcarbonyl group A ring having 1 to 5 substituents selected from a C ₁ -C ₆ alkoxycarbonyl group, a mono C ₁ -C ₆ alkylamino group, or a di C ₁ -C ₆ alkylamino group which may be the same or different A substituted phenylamino group, a phenoxy group or the same or different, halogen atom, cyano group, nitro group, hydroxyl group, amino group, SH group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C _2- C ₆ alkenyl group, halo C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, halo C ₂ -C ₆ alkynyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₂ -C ₆ A Keniruchio group, halo C ₂ -C ₆ alkenylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁
-C ₆ alkylsulfonyl group, C ₁ -C ₆ alkylcarbonyl group, halo C ₁ -C ₆ alkylcarbonyl group, phenylcarbonyl group, C ₁ -C ₆ alkoxycarbonyl group, mono C ₁ -C ₆ alkylamino group or the same Or a substituted phenoxy group having 1 to 5 substituents selected from di-C ₁ -C ₆ alkylamino groups which may be different from each other on the ring;
R ² is a hydrogen atom, C ₁ -C ₈ alkyl group, C ₂ -C ₈ alkenyl group, C ₂ -C ₈ alkynyl group, C ₁ -C ₈ alkoxy C ₁ -C ₈ alkyl group, cyano C ₁ -C ₈ Alkyl group, C ₁ -C ₈ alkylcarbonyl group, halo C
₁ -C ₈ alkylcarbonyl group, C ₂ -C ₈ alkenyl group, a C ₁ -C ₈ alkylsulfonyl group or a halo C ₁ -C ₈ alkylsulfonyl group shown.
R ³ may be the same or different and is a halogen atom, a C ₁ -C ₈ alkyl group, a halo C ₁ -C ₈ alkyl group, a C ₂ -C ₈ alkenyl group, a halo C ₂ -C ₈ alkenyl group, C _2- C ₈ alkynyl group, halo C ₂ -C ₈ alkynyl group, C ₁ -C ₈ alkoxy group, halo C ₁ -C ₈ alkoxy group, C ₁ -C ₈ alkoxy C ₁ -C ₈ alkyl group, halo C ₁ -C ₈ alkoxy C ₁ -C ₈ alkyl group, C ₁ -C ₈ alkoxy C ₁ -C ₈ alkoxy group, halo C ₁
-C ₈ alkoxy C ₁ -C ₈ alkoxy group, C ₁ -C ₈ alkylsulfonyl group, halo C ₁ -C ₈ alkylsulfonyl group, C ₁ -C ₈ alkylthio group, halo C ₁ -C ₈ alkylthio group, C ₁ -C ₈ alkylsulfinyl group, halo C ₁ -C ₈ alkylsulfinyl group, C ₁ -C ₈ alkylsulfonyl group, halo C ₁ -C ₈ alkylsulfonyl group, C ₁ -C ₈ alkylcarbonyl group, C _1- C ₈ alkoxycarbonyl group, C ₁ -C ₈ alkylcarbonyloxy group, halo C ₁ -C ₈ alkylcarbonyloxy group, a hydroxyl group, a formyl group, a cyano group, a nitro group, a trimethylsilyl group, pentafluorosulfur sulfonyl group (-SF ₅ ) Or -C (R ⁴ ) = NOR ⁵ (wherein R ⁴ and R ⁵ may be the same or different and each represents a hydrogen atom, a C ₁ -C ₅ alkyl group or a halo C ₁ -C ₅ alkyl group). ) And two adjacent groups ³ together with each other difluoromethylenedioxy group (-OC
F ₂ O—), a tetrafluoroethylenedioxy group (—OCF ₂ CF ₂ O—), a methylenedioxy group, or an ethylenedioxy group.
G may be the same or different, and —C (═O) —, —C (═S) —, or —C (R ⁶ ) ₂ — (
In the formula, R ⁶ may be the same or different and each represents a hydrogen atom, a cyano group or a C ₁ -C ₈ alkyl group,
And two R ⁶ groups together contain 3-6 carbon atoms, nitrogen atoms, oxygen atoms or sulfur atoms.
Member rings can be formed. )
X represents a single bond, a group represented by —C (═O) —, —C (═S) — or —SOq— (wherein q represents 1 or 2).
Y may be the same or different, and CR ⁷ (wherein R ⁷ is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a carboxyl group, a pentafluorosulfanyl group (-SF ₅ ), C _1-
C ₈ alkyl group, halo C ₁ -C ₈ alkyl group, C ₂ -C ₈ alkenyl group, C ₂ -C ₈ alkynyl group, C ₁ -C ₈ alkoxy group, halo C ₁ -C ₈ alkoxy group, C _1- C ₈ alkoxycarbonyl group, C ₁ -C ₈ alkylthio group, C ₁ -C ₈ alkylsulfinyl group, C ₁ -C ₈ alkylsulfonyl group, C ₁ -C ₈ alkylamino group or di-C ₁ which may be the same or different —C _{8 represents} an alkylamino group. ) Or N → (O
) P (wherein p represents an integer of 0 or 1), and at least two Y are N → (O) p
(Wherein p is the same as above).
t represents an integer of 0 to 2, and m represents an integer of 1 to 5. } Or a salt thereof. R ¹ is a hydrogen atom, C ₁ -C ₈ alkyl group, halo C ₁ -C ₈ alkyl group, C ₂ -C ₈ alkenyl group, C ₁ -C ₈
An alkoxy group, a mono C ₁ -C ₈ alkylamino group, a di C ₁ -C ₈ alkylamino group which may be the same or different, a phenyl group or the same or different, from a halogen atom or a C ₁ -C ₈ alkyl group A substituted phenyl group substituted with 1 to 5 selected, R ² is a hydrogen atom, C ₁ -C ₈
Alkyl group, a C ₁ -C ₈ alkoxy C ₁ -C ₈ alkyl group or C ₁ -C ₈ alkyl group,
R ³ may be the same or different, C ₁ -C ₈ alkyl group, halo C ₁ -C ₈ alkyl group, C ₁ -C ₈ alkoxy group, halo C ₁ -C ₈ alkoxy group, C ₁ -C ₈ alkoxy group C ₁ -C ₈ alkoxy group, C ₁ -C ₈ alkylthio group, C ₁ -C ₈ alkylsulfinyl group, C ₁ -C ₈ alkylsulfonyl group, C ₁ -C ₈ alkylcarbonyl group, a formyl group, a nitro group, a cyano Group, hydroxyl group, trimethylsilyl group, -C (R ⁴ )
= NOR ⁵ (wherein R ⁴ and R ⁵ are the same as in claim 1), a methylenedioxy group, a difluoromethylenedioxy group (—OCF ₂ O—) or a tetrafluoroethylenedioxy group (—OCF ₂ CF ₂ O—) and G is —C (═O) —, —C (═S) or —C (R ⁶
) _2- (wherein R ⁶ may be the same or different and represents a hydrogen atom or a C ₁ -C ₈ alkyl group.)
The phenylheteroaryls or salts thereof according to claim 1, which is a group represented by the formula: R ¹ may be a C ₁ -C ₅ alkyl group, a halo C ₁ -C ₅ alkyl group or the same or different and is selected from a halogen atom, a halo C ₁ -C ₅ alkyl group or a halo C ₁ -C ₅ alkoxy group The phenyl heteroaryls or salts thereof according to claim 1, which is a phenyl group having one or more substituents. The R ³ may be the same or different and is a halo C ₁ -C ₅ alkyl group, a halo C ₁ -C ₅ alkoxy group or a difluoromethylenedioxy group (—OCF ₂ O—). Or a salt thereof. A herbicide containing the phenylheteroaryls or salts thereof according to any one of claims 1 to 4 as an active ingredient. A method for using a herbicide, which comprises treating an effective amount of the herbicide according to claim 5 with soil or a plant.