WO2001079200A1

WO2001079200A1 - Pyrazole derivatives and herbicides containing the same

Info

Publication number: WO2001079200A1
Application number: PCT/JP2001/003232
Authority: WO
Inventors: Ichiro Nasuno; Mitsuru Shibata; Kazuyoshi Koike
Original assignee: Idemitsu Kosan Co., Ltd.
Priority date: 2000-04-19
Filing date: 2001-04-16
Publication date: 2001-10-25
Also published as: AR028352A1; AU4692001A

Abstract

Herbicides containing as the active ingredient pyrazole derivatives of the general formula (I) and/or salts thereof, (wherein each symbol is as defined in the description). The pyrazole derivatives and the salts do not cause chemical damage to upland crops such as corn, and can control a wide variety of upland weeds even in a low dosage.

Description

Description Virazol derivative and herbicide using the same

Technical field

The present invention relates to a novel pyrazole derivative and a herbicide using the same. More specifically, the present invention relates to a pyrazole derivative capable of controlling a wide range of field weeds at a low dose without causing phytotoxicity to field cultivated crops such as corn, and a herbicidal composition containing the villazonole derivative as an active ingredient It relates to the agent. Background art

Herbicides are extremely important for labor saving in weed control and for improving the productivity of agricultural and horticultural crops.Therefore, research and development of herbicides has been actively carried out for many years, and a wide variety of chemicals are currently in practical use. ing. However, even today, there is a demand for the development of new drugs that have more excellent herbicidal properties, especially those that can control only the target weeds selectively and at a low dose without causing phytotoxicity to cultivated crops. ing.

Conventionally, at the time of cultivation of corn and the like, atrazine (atrazine), which is a triazine herbicide, and alarachlor (a 1 achlor) and metolachlor (me tolachlor), which are acid-based herbicides, have been used. Atrazine has a low activity against grass weeds, and aclarol and metolachlor have low activities against broadleaf weeds. Therefore, it is currently difficult to control gramineous and broadleaf weeds at once with a single agent. In addition, these herbicides require high doses and are not preferred on environmental issues.

By the way, it is known that certain 4-benzoyl derivatives have herbicidal activity (Japanese Patent Application Laid-Open Nos. 631-222672, 63-122222, and 633-1). No. 703665, JP-A-11-52759, JP-A-2-1733, JP-A-2-288886), and as a herbicide that is currently commercially available, a pyrazolate represented by the following chemical formula (pyrazolate) »Ah ^).

However, although these 4-benzoyl derivatives have herbicidal activity, they are practically insufficient, and in particular, have significantly poor herbicidal activity against grass weeds such as nobies and enokorodasa. In order to solve these disadvantages, a compound in which a chiochroman ring and a villazonole ring are bonded has been filed as a patent application (WO 95/05054). Representative examples of the compounds described in this publication are shown below.

These chiochroman derivatives have a higher herbicidal activity than the 4-benzoyl derivatives, but are not sufficient. In addition, the safety of corn is insufficient. Disclosure of the invention

The present invention provides a novel compound capable of controlling a wide range of field weeds at a low dose without causing phytotoxicity to field-cultivated crops such as corn under such a circumstance. It is intended to provide high-performance herbicides for agricultural or non-agricultural use.

The present inventors have conducted intensive studies to achieve the above object, and as a result, have found that a pyrazole-based compound having a specific structure can achieve the object. The present invention has been completed based on this finding. That is, the present invention provides a compound represented by the general formula (I

Where X is an oxygen atom, or

,

(However, when X represents a left-right asymmetric group, the bond on the left is bonded to the benzene ring, and the bond on the right is bonded to the Y moiety.)

Y is the formula

R ²⁸ R ³⁰ R ²⁸ R ³¹ R ²⁸ R ³⁰ R ²⁸ R ³¹ R '

1 1 1 1 1

― C1 ~ N-1 C-1 C-1 C— -N—— — C— -C— -C

29 9 32 1,

RR ²⁹ R ²⁹ R ³² R

28

RR ²⁸

— 0-1 — C-0

»I-one S-one or —? — S

.29, 29

R

(However, when Y represents a left-right asymmetric group, the bond on the left is bonded to the X part, and the bond on the right is bonded to the Z part.)

z is an oxygen atom or formula

-S-S- _Y

O _M 0 ₂ '

-N— C——

(However, when Z represents a left-right asymmetric group, the bond on the left is bonded to the benzene ring, and the bond on the right is bonded to the Y moiety.)

However, the following general formula (V):

In substituent represented is, when bonded to the benzene ring in the meta position with respect to R ⁵ is, Zeta gar S Omicron ₂ - is not a.

Υ is the formula

R ³⁰

~ Ν—

When X is a group represented by the formula:

R ²⁶

C = N

It cannot be a group represented by.

Y is the expression

R 30 p28p30

—— N— or —— C I-one N-

When it is a group represented by IT, 29, Z is represented by the formula 1 0— S— or 1 S— 0—

o ₂ 0 is not a group represented by _2.

When Y represents an oxygen atom, X is represented by the formula R 'R ²⁶ R ²⁷

— C— or 1 represents a group represented by c = c, and z is a group represented by the formula

Represents a group represented by

When Υ represents a sulfur atom, X is represented by the formula

R ⁷ R ²⁶ R ²⁷ c— or a group represented by c = c, and z is a group represented by the formula

X 35 II

— C or one c

The group represented by R 36 is shown.

Y is the expression

X is an oxygen atom or a group represented by the formula

13

And Z represents a group represented by the formula one

Represents a group represented by

Q is a substituted or unsubstituted naphthyl group, which is condensed or not condensed with a benzene ring, which may be interrupted by one or two oxygen atoms and Z or a sulfur atom, substituted or unsubstituted cycloalkyl group C ₃ -C ₆ of, C ₄ cycloalkenyl group ~ c ₆ containing or oxygen, the heteroatom one to three pieces selected from among nitrogen and sulfur atoms, becomes condensed with a benzene ring or A substituted or unsubstituted 5- or 6-membered aromatic heterocyclic group, which is not fused, and an ethylene oxide group which may be substituted with a C i -C ₄ alkyl group. The sulfur atom contained in the cycloalkyl and cycloalkenyl groups may be partially or completely oxidized by oxygen.

R ¹ and R ² each independently represent a hydrogen atom, a halogen atom, a Ci C alkyl group or a C i -C ₄ alkyl group.

R ³ may be interrupted by a hydrogen atom, one or two oxygen atoms and a hydrogen atom or a sulfur atom, and may have a halogen atom.C i Ce chain alkyl group or C ₃ to C ₃ ₆ cyclic alkyl group or a C ₂ -C ₆ alkenyl group,, C ₂ -C ₆ Haroaru Kenyir group, a c ₂ to c ₆ alkynyl group, the sulfur atom is partially young properly by oxygen is fully oxidized Is also good.

R ⁴ is a hydrogen atom, one or two oxygen atoms and Roh or may be interrupted by a sulfur atom, also good Ci Cs-chain alkyl group which may have a halogen atom, there Rere is C ₂ ~ A C ₆ alkenyl group, a C ₂ -C ₆ haloalkenyl group, a C ₂ -C ₆ alkynyl group, a cyano group, a carboxyl group or a (Ci-C ₄ alkoxy) carbonyl group; Partially or fully oxidized

You may.

R ⁵ is a hydrogen atom, a halogen atom, a nitro group, one or two oxygen atoms and or sulfur atoms which may be interrupted by, also have may 〇 ₁ ～〇 a halogen atom ₆ chain Arukiru Group or. ₃ ～〇 ₆ cyclic Arukiru group or a carboxyl group, Shiano group, Chioshiano group, C i~C ₄ alkoxyl group, C I～C Bruno, Roarukokishiru Group, (C ₁ -C ₄ alkoxy) carbonyl group, a mercapto group, alkylthio O group, Ci～c ₄ alkylsulfinyl group, C i~C ₄ alkylsulfonyl group, c ₂ -C ₆ Arukeninore group, C ₂ -C ₆ Haroanorekeyuru group, or a C ₂ -C ₆ Anorekiniru group, a sulfur atom contained in the C i~C ₆ chain alkyl group or a C ₃ -C ₆ cyclic alkyl groups being partially or completely oxidized by oxygen Is also good.

R ⁶ is a halogen atom, a nitro group, one or two oxygen atoms and Roh or sulfur atom may be interrupted by, also have good Ci Ce-chain alkyl group or a C ₃ be ~ a halogen atom C ₆ cyclic alkyl group or a carboxyl group, Shiano group, Chioshiano groups, C alkoxyl group, Ji ~ Ji haloalkoxyl group, (〇丄-C ₄ alkoxy) carbonyl group, a mercapto groups, C alkylthio group,

-C ₄ alkylsulfinyl group, C ₁ -C ₄ alkyl sulfonyl Honoré group, C ₂ -C ₆ Anore Kenyir group, C ₂ -C ₆ haloalkenyl group, or a c ₂ to c ₆ Arukieru group, the C i The sulfur atom contained in the -C ₆ chain alkyl group or the C ₃ -C ₆ cyclic alkyl group may be partially or completely oxidized by oxygen.

Xi X ⁷ represents an oxygen atom or a sulfur atom, respectively.

R ⁷ and R ⁸ may be each independently interrupted by a hydrogen atom, a halogen atom, a nitro group, one or two oxygen atoms and / or sulfur atoms, and have a halogen atom. which may be Ci～C ₆ chain alkyl group or a C ₃ -C ₆ cyclic alkyl group or a carboxyl group, Shiano group, C i~C ₄ alkoxyl group, Ci～C ₄ halo Ano record hexyl group, (C ₁ -C ₄ Azorekokishi) carbonyl group, 〇～〇 alkyl Chiomoto, 〇～〇 alkylsulfide El group, C i~C ₄ alkylsulfonyl group, the ^{_{formula: - CHR 37 N0 2, -CHR}} 37 NR 13 R 14, - CHR ³⁷ P (= 0) (〇R ³⁸ ) ₂ , — NR ¹³ R ¹⁴ , _NR ³⁷ COR ³⁹ , _NR ³⁷ C0 ₂ R ³⁸ , -NR ³⁷ S0 ₂ R ³⁹ , — OCOR ³⁹ , —〇C0 ₂ R ³⁷ , — OCONR ¹³ R ¹⁴ , one OCHR ³⁷ CN, one CHR ³⁷ COR ³⁹ , — OCHR ³⁷ C0 ₂ R ³⁸ ′ —〇 C HR ³⁷ CONR ¹³ R ¹⁴ , — S0 ₂ NR ¹³ R ¹⁴ , one OS〇 ₂ R ³⁹ , — O— N = C R ¹³ R ³⁷ , one P (= 0) (OR ³⁸ ) ₂ , —OP (= 0) (OR ³⁸ ) ₂ , a substituted or unsubstituted phenyl group, or a substituted or unsubstituted phenyl group a 5- or 6-membered aromatic heterocyclic group ring shows, the Ci Ce-chain alkyl group or a C ₃ -C _s sulfur atom in the cyclic alkyl group'm connexion partially or completely in the oxygen It may be oxidized. R ⁹ represents a hydrogen atom, a Ci Cs alkyl group, a Ci Cs haloalkyl group, one COR ³⁹ or one S ₂ R ³⁹ .

R ^1G may be interrupted by a hydrogen atom, one or two oxygen atoms and Z or sulfur atom, and may have a halogen atom. Ci Cs chain alkyl group or C ₃ -C ₆ Cyclic alkyl group, or C ₂ -C ₆ alkenyl group, C ₂ -C ₆ haloalkenyl group, C ₂ -C ₆ alkynyl group, or formula: — COR ³⁹ , —C 0 ₂ R ³⁷ , -CH R ³⁷ CN,- ^{^{^{CHR 37 COR 39, - CHR 37}}} CO 2 R 38, -CHR 37 CONR 1 3 R 14, -CONR 13 R 14, - S_〇 a group represented by ₂ R ^39, the C Cs linear alkyl group, or C ₃ ~ C ₆ sulfur atoms in the cyclic alkyl group may be partially or completely oxidized by oxygen.

R ¹¹ and R ¹² are each independently a hydrogen atom, a nitro group, a carboxyl group, shea Anomoto, C -C ₄ alkyl group, C i~C ₄ haloalkyl group, (Ji-Ji alkoxy) carbonyl group or one Indicates COR ³⁹ .

R ¹³ represents a hydrogen atom, a C Ce alkyl group, 〇 to 、, an alkyl group or a substituted or unsubstituted phenyl group.

R ¹⁴ is a hydrogen atom, a halogen atom,. ~ 〇 alkyl group or.じ represents a haloalkyl group.

R ^{15 to} R ²³ , R ²⁶ and R ²⁷ are each a hydrogen atom, a halogen atom,.じ represents an alkyl group or C〜 or an alkyl group.

R ²⁴ and R ²⁵ are each a hydrogen atom, a halogen atom, Ci～C ₄ alkyl groups, C I～C ₄ haloalkyl groups, C i C Anorekokishiru groups, C丄~ Ji haloalkoxyl group, a carboxyl group, (C ₁ - C ₄ anoreoxy) carbonyl group, C ₁ -C ₄ alkylthio group, and so on. It represents an alkylsulfiel group, a C i -C ₄ alkylsulfonyl group, an amino group, a mono (CC alkyl) amino group or a di (di-alkyl) amino group.

R ²⁸ , shaku ²⁹ and shaku ³¹ ~! ¾ ³⁴ are each a hydrogen atom, a halogen atom,

It represents an alkyl group or Ci to C ^, and an alkyl group.

R ³⁵ and R ³⁶ each independently represent a hydrogen atom, a halogen atom, a CiC alkyl group, a C i -C ₄ haloalkyl group, a C alkoxyl group, or R ³

⁵ , R ³⁶ and the carbon atom to which they are attached, together form the formula: , R ¹³

\

May be formed.

R ³⁰ , R ³⁷ , R ³⁸ and R ^4G each represent a hydrogen atom or an alkyl group.

3 ^{9 to} ₁ to ₄ alkyl groups. 〜 Represents an alkyl group or a substituted or unsubstituted phenyl group.

k represents the length of the methylene chain and is 0, 1 or 2.

n is 0 or 1.

m, p and q each represent 0, 1 or 2, when p is 2, two R ²⁴ of N RI may be the same or different, and when q is 2, two R ⁶ Each of which may be the same or different). The present invention also provides a herbicide containing the pyrazole derivative and Z or a salt thereof as an active ingredient. BEST MODE FOR CARRYING OUT THE INVENTION

First, the pyrazole derivative of the present invention will be described.

The pyrazole derivative of the present invention has the general formula (I)

It is a compound represented by these.

In the general formula (I), X is an oxygen atom or a formula

ει

0 / lOdf / 丄 :) d 00Z6m / 10 OM R

Four

o

7

Where X represents an asymmetric group, the bond on the left is bonded to the benzene ring, and the bond on the right is bonded to the Y moiety.

Y is the formula

―

28, 28

R

-O—, — C-O—, one S—, or one C—S—

'^ 29' indicates the group represented by '29, but when Y represents an asymmetric group, the bond on the left is bonded to the X part and the bond on the right is bonded to the Z part.

On the other hand, Z is an oxygen atom, or the formula

35 40

R R

― S C—— —— C— — 0-S—— One S-0— — N— S—— or O ^ 36 〇2 〇2 ° 2

-N— represents a group represented by C-, but when Z represents an asymmetric group, the bond on the left _T is connected to the zen ring, and the bond on the right is connected to the Y part

However, the following general formula (V):

When the substituent represented by is bonded to the benzene ring at the meta position to R ⁵ , Z is not —S ー₂ —.

Y is the expression

• N '

When X is a group represented by the formula:

, 26

R

— C = N '

It is not a group represented by

Y is the expression

R 30 τ¾28 ρ30

~ Ν—— or one C-N one

When R is a group represented by R 29,

0-S— or —— S-O

0 is not a ₂ 0 ₂ in a group represented by.

When Υ represents an oxygen atom, X is represented by the formula

R ^2o R ²⁷

— Represents a group represented by C or c = c—, and Z is a group represented by the formula — C—,

Represents a group represented by

If Y is a sulfur atom, X is

Wherein Z is a group represented by the formula

Represents a group represented by

Y is the expression

X is an oxygen atom or a group represented by the formula

Represents any of the groups represented by

Represents a group represented by Q is a substituted or unsubstituted naphthyl group, which is condensed or not condensed with a benzene ring, which may be interrupted by one or two oxygen atoms and / or sulfur atoms, C ₃ -C cycloalkyl group _6, C ₄ ~ cycloalkenyl group C ₆ or oxygen, nitrogen and a heteroatom 1-3 pieces selected from among sulfur atom, formed by condensation with a benzene ring or fused, and it has not substituted or unsubstituted 5-membered or 6-membered aromatic heterocyclic group, yet represents a C ₁ -C ₄ 7 alkyl optionally Echirenokishido group optionally substituted with a group. The sulfur atom contained in the cycloalkyl and cycloalkenyl groups may be partially or completely oxidized by oxygen.

If having the naphthyl group, a cycloalkyl group or Shikuroaruke two Le group substituents of C ₄ -C ₆ of C ₃ -C _6, Examples of the substituent include a halogen atom, a nitro group, a carboxyl group, Shiano group, CC alkyl group, C to C, mouth alkyl group,

C I～C ₄ alkoxyl group, 〇～〇, Roarukokishiru group, 1 or selected from among (Ci C alkoxy) carbonyl group, c ～〇 ₄ alkylthio group, Ci～c ₄ alkylsulfinyl group and CC an alkylsulfonyl group Two groups can be mentioned preferably. Examples of the C ₃ -C ₆ cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. Examples of the C ₄ -C ₆ cycloalkenyl group include a cyclobutyl group, a cyclopentenyl group, Xenyl group.

Examples of the C _{3 to} C ₆ cycloalkyl group and the C _{4 to} C ₆ cycloalkyl group condensed with a benzene ring include those obtained by condensing a benzene ring with each of the groups exemplified above. A benzene ring condensed with one not or 2 oxygen atoms and Roh or cycloalkyl group which may be interrupted by a sulfur atom C ₃ -C _6, examples of cycloalkyl alkenyl group c ₄ to c ₆ and preferably Things include:

(£ ¹ and £ ² each represent an oxygen atom or a sulfur atom). The sulfur atom contained in each of the above structures may be partially oxidized by oxygen to be a sulfoxide (S〇) or completely oxidized to be a sulfone (S〇 ₂ ).

Examples of a benzene ring fused with one composed or two oxygen atoms and / or cycloalkyl group optionally C ₃ -C ₆ also therefore be interrupted by a sulfur atom, Shikuroa alkenyl group of C ₄ -C ₆ and Preferably,

And the like.

The sulfur atom contained in each of the above structures may be partially oxidized by oxygen to be a sulfoxide (so) or completely oxidized to be a sulfone (so ₂ ).

Of these, especially

Is preferred.

When the 5- or 6-membered aromatic heterocyclic group not condensed with the benzene ring has a substituent on the ring, or the 5- or 6-membered aromatic group condensed with the benzene ring When the heterocyclic group has a substituent on the benzene ring and / or the heterocyclic ring, examples of such a substituent include a halogen atom, a cyano group, a nitro group, a carboxy group, a hydroxy group, a hydroxy group, an amino group, Mono (C i C alkyl) amino group, di (C i -C ₄ alkyl) amino group, 〜 ~. Alkyl groups, C I～C, mouth alkyl groups, C alkoxyl groups, C i C ^ Roarukokishiru group, (Ji ~. Alkyl) force carbonyl group, (. ~ Ji alkoxy) carbonyl groups, C I～C ₄ alkylthio groups , mention may be made preferably from 1 to 3 groups selected from among C alkylsulfinyl group and Ci～c ₄ alkylsulfonyl group.

Examples of 5-membered aromatic heterocyclic groups not containing a benzene ring and containing 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur atoms include furan, thiophene thiophene), pyrrole (pyrrole), oxazonole (oxazole), thiazonole (thiazole), imidazonole (imidazole) Residues such as thiadiazole and triazole are listed. Examples of a 6-membered aromatic heterocyclic group which does not condense with a benzene ring and has 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur atoms include pyridine (.pyridine), Residues such as biligcine (pyridazine, pyrimidine (.pyrimidine), pyrazine (prazine), triazine (triazine), oxaziazine (oxadiazine), and thiaziazine (thiadiazine) are included, while oxygen, nitrogen and sulfur atoms are included. Examples of a 5- or 6-membered aromatic heterocyclic group condensed with a benzene ring containing 1 to 3 heteroatoms selected from benzofliran, benzothiophene, and indone (Indole), benzoxazole, benzothiazole (benzothiazole), benzimidazono (benzimidazole), benzoisothiazole (benzoisothiazole), indazoino

(indazole), benzothiadiazole, quinoline, quinoline, isoquinoline, cinnoline, phthalazine, phthalazine, quinazoline, and quinoxaline.

Preferred examples of the 5- or 6-membered aromatic heterocyclic group not condensed with the benzene ring include furan, thiophene, oxazole, thiazole, isoxazole, isothiazole, pyridine, pyrimidine and triazine residues. More preferred are furan, thiophene, thiazole, isoxazole and pyridine residues, and particularly preferred are thiophene and pyridine residues.

On the other hand, preferred 5- or 6-membered aromatic heterocyclic groups fused to a benzene ring include benzothiophene, benzoxazonole and benzothiazonole residues. In addition, substituents bonded on the ring of the 5- or 6-membered aromatic heterocyclic group not condensed with a benzene ring, or 5- or 6-membered aromaticity condensed with a benzene ring Preferred examples of the substituent bonded to the benzene ring and Z or the heterocyclic ring of the tetracyclic group include a halogen atom, a carboxyl group, a C i -C ₄ alkyl group, a C -dialkyl group and a dialkyl group. , C alkoxyl group and

To C ₄ alkoxy) carbonyl group, more preferably, a nitrogen atom, an alkyl group, a C i C ^ opening alkyl group and a (C i C alkoxy) carbonyl group. Chlorine atom, methyl Group, _COOCH ₃ and one CO〇C ₂ H ₅ .

Examples of the ethylene oxide group which may be substituted with an alkyl group of Ci C include, for example,

And the like.

1 ^ ¹ and 1¾ ² each independently represent a hydrogen atom, Ji ₁ ～〇 ₄ Arukiru group or 〇 ₁ ～〇 ₄ haloalkyl group. Preferred examples of R ¹ and R ² include a hydrogen atom and a Ci C alkyl group, and particularly preferred are a hydrogen atom and a methyl group.

k represents the length of a methylene chain, and is ◦, 1 or 2, and preferred k is 1. R ³ may be interrupted by a hydrogen atom, one or two oxygen atoms and / or sulfur atoms, and may have a halogen atom. Ci-C ₆ chain alkyl group or C ₃ -C _A hexacyclic alkyl group, or a C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ haloalkenyl group, or a C ₂ -C ₆ alkynyl group, wherein the sulfur atom may be partially or completely oxidized by oxygen; Good.

Among such R ³ , preferred are a hydrogen atom, one or two oxygen atoms and a C ₆ -C ₆ alkyl group which may be interrupted by a hydrogen atom or a sulfur atom, C ₁ -C 4, Examples thereof include an alkyl group and a C ₃ to C ₆ cycloalkyl group. More preferable examples include a hydrogen atom and a C ₄ to C ₄ alkyl group. Particularly preferable examples include a methyl group, an ethyl group and An isopropyl group can be mentioned.

R ⁴ may be interrupted by a hydrogen atom, one or two oxygen atoms and / or sulfur atoms, and may have a halogen atom. Ci C ₆ chain alkyl group, or C ₂ -C ₆ alkenyl group, C ₂ -C ₆ haloalkenyl group, C ₂ -C ₆ Arukini group, indicates Shiano group, a carboxyl group or a (Ji ~. alkoxy) carbonylation group, the sulfur atom is partially or by oxygen It may be completely oxidized. Among such R ⁴ , preferred are a C ₆ to C ₆ alkyl group which may be interrupted by a hydrogen atom, one or two oxygen atoms and / or a sulfur atom, Examples include C i Ce haloalkyl groups and C ₃ -C ₆ cycloalkyl groups, and further include carboxyl groups and (di-alkoxy) carbonyl groups, and more preferred are a hydrogen atom and a Ci C alkyl group. And particularly preferred are a hydrogen atom and a methyl group.

R ⁵ is a hydrogen atom, a halogen atom, a nitro group, one or two oxygen atoms and

It may be interrupted by Z or sulfur atom, and may have halogen atom

C i Ce chain alkyl group or C ₃ -C ₆ cyclic alkyl group, or carboxyl group, cyano group, thiocyano group, C i -C ₄ alkoxyl group, C -di, loalkoxyl group, (di -di alkoxy) carbonyl Groups, mercapto groups, and so on. Alkylthio group, C ~. ₄ Alkylsulfinyl groups. Alkylsulfonyl group, C ₂

Represents a C ₆ -alkenyl group, a C ₂ -C ₆ haloalkenyl group or a C ₂ -C ₆ alkynyl group, and is a sulfur atom contained in the Ci-C ₆ chain alkyl group or the C ₃ -C ₆ cyclic alkyl group. May be partially or completely oxidized by oxygen.

Among such R ⁵ , preferred are a halogen atom, a nitro group, one or two oxygen atoms and / or an optionally interrupted Ci C

₆ alkyl groups and Ci to C, mouth alkyl groups and 〇 _{3 to} 〇 ₆ cycloalkyl groups, and also cyano groups, C 1 to C ₄ alkoxyl groups, C to chloroalkoxyl groups, 〇 to アルキル alkylthio groups, C i -C ₄ alkyl sulfide El group and C I～C can be exemplified ₄ alkylsulfonyl group, and more preferred are a halogen atom, a nitro group, CC alkyl group, 〇 _1. ₄ haloalkyl groups and. It can be mentioned ₁ ～〇 ₄ Arukirusuruho group, as particularly preferable, and a halogen atom, a nitro group and Ci～c ₄ alkyl group.

R ⁶ is a halogen atom, a nitro group, one or two oxygen atoms and / or sulfur atom may be interrupted by, also have good Ci Cs-chain alkyl group or a C ₃ be ~ a halogen atom C ₆ cyclic alkyl group, or carboxyl group, cyano group, thiocyano group, C alkoxyl group, C to C ₄ haloalkoxyl group,

~ C ₄ alkoxy) carbonyl group, mercapto group, CC alkylthio group,

~C ₄ alkyl sulfide El group, Ji丄~. Alkylsulfonyl group, C ₂ -C ₆ Anore Kenyir group, a C ₂ -C ₆ haloalkenyl group or a C ₂ -C ₆ alkynyl group, the C i~C ₆ chain alkyl group or a C ₃ -C ₆ cycloalkyl The sulfur atom contained in the group is oxygen May be partially or completely oxidized.

Among such R ^6, the preferred halogen atom, a nitro group, CJ ~ C ₄ alkyl group, C t~ C ₄ C port alkyl and C! To C ₄ alkylsulfonyl group, more preferably, halogen atom, nitro group and. ~. Alkyl groups can be mentioned, and particularly preferred are di- to alkyl groups. Most preferred are methyl groups.

Xi～X ⁷ is independently an oxygen atom or a sulfur atom, are preferred oxygen atoms. Shaku ⁷ and! ⁸ each may be independently interrupted by a hydrogen atom, a halogen atom, a nitro group, one or two oxygen atoms and a Z or sulfur atom, and have a halogen atom. A C i -C ₆ chain alkyl group or a C ₃ -C ₆ cyclic alkyl group, or a carboxyl group, a cyano group, a C -dialkoxyl group,

Noloalkoxyl group, (CC anorekoxy) carbonyl group, and so on. Arukinore Chiomoto, Ci～c ₄ alkylsulfinyl group, Ci～c ₄ alkylsulfonyl group, the ^{_{formula: - CHR 37 N0 2, -CHR}} 37 NR 13 R 14, - CHR 37 P (= 0) (OR 38) 2, ^{^{^{- NR 13 R 14, -NR 37}}} COR 39, - NR 37 C0 2 R 38, - NR 37 S0 2 R 39, -OCOR 39, -OC0 2 R 37, -OCONR 13 R 14, _OCHR 37 CN, - O CHR ³⁷ COR ^39, one OCHR ³⁷ C0 ₂ R ³⁸ '-〇 ^{^{^{CHR 37 C ON R 13 R 14}}} , - S0 2 NR 13 R 14, -〇_S0 _{^{2 R 39, -0-N =}} CR 13 R 37, - P (= 0) (OR ³⁸ ) ₂ , OP (= 0) (OR ³⁸ ) ₂ , substituted or unsubstituted phenyl group, or substituted or unsubstituted 5- or 6-membered ring The sulfur atom contained in the above-mentioned _6- chain alkyl group or the C ₃ -C ₆ cyclic alkyl group may be partially or completely oxidized by oxygen.

In the case where the above-mentioned furyl group 複素 aromatic heterocyclic group has a substituent, examples of the substituent include a halogen atom, a nitro group, a carboxyl group, a cyano group, a CiCT alkyl group, a C〜 Alkyl group, C i C alkoxyl group,. ₁ ～〇 ₄ Haroa Norekokishiru group, (Ci～C ₄ alkoxy) carbonyl group, an alkylthio group,

One or two groups selected from a C ₄ -C ₄ alkylsulfinyl group and a C ₄ -C ₄ alkylsulfonyl group are preferred.

Among such R ⁷ and R ⁸ , a preferable one is a hydrogen atom, Two oxygen atoms and Roh or may be interrupted by a sulfur atom C i~C ₆ alkyl Le group Ya C ₁ -C ₆ haloalkyl group, more Ci C alkoxyl group, the. ~ Haloalkoxyl group, C i~C ₄ alkylthio group, C i~C ₄ alkylsulfinyl group, C i~C ₄ alkylsulfonyl group and the formula: A OCOR ^39, one 〇_C_〇 ₂ R ^37, - OC_〇_NR ¹³ R ^14, -OCHR ³⁷ CN, one OChr ³⁷ C_〇 R ^39, one OCHR ³⁷ C0 ₂ R ^38, can be a group represented by one 〇_CHR ³⁷ CONR ¹³ R ^14, as preferred Ri yo is Ci Ce alkyl group which may be interrupted by hydrogen atom, 1 or 2 oxygen atoms and / or sulfur atoms, and Ci to C ₄ alkoxy groups and C _{1 to} C and lower alkoxyl groups Particularly preferred are a hydrogen atom, a CiC alkyl group and a CiC alkoxyl group, and most preferred are a hydrogen atom, a methyl group and a methoxy group.

R ⁹ is a hydrogen atom, C Cs alkyl group, C -C ₆ haloalkyl group, - shows a COR ³⁹ or over 3_Rei ₂ 1 ^39.

Among these R ⁹ , preferred are a hydrogen atom and a Ci Ce alkyl group, and more preferred are a hydrogen atom, a methyl group and an ethyl group.

R ^1Q may be interrupted by a hydrogen atom, one or two oxygen atoms and / or sulfur atoms, and may have a halogen atom. Ci Cs chain alkyl group or C ₃ -C ₆ cyclic An alkyl group, or a C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ haloalkenyl group, a C ₂ -C ₆ alkynyl group, or a formula: — COR ³⁹ , one C〇 ₂ R ³⁷ , —CH R ³⁷ CN, − CHR ³⁷ COR ^39, one ^{_{^{CHR 37 CO 2 R 38, -CHR}}} ^ CONR 1 3 R 14, one CONR ¹³ R ^14, - S_〇 a group represented by ₂ R ^39, the C Cs linear alkyl group, or C ₃ -C ₆ sulfur atoms in the cyclic alkyl group may be partially or completely oxidized by oxygen.

R ¹ like this. Among them, preferred are a hydrogen atom, one or two oxygen atoms and a CiCs alkyl group or a C Ce haloalkyl group which may be interrupted by a Z or sulfur atom, and also a C ₂ -C ₆ alkenyl. group, C ₂ -C ₆ can be cited Haroaruke alkenyl group and C ₂ -C ₆ alkynyl group, more preferred are a hydrogen atom, and CC alkyl group. The ability to name an alkyl group; Particularly preferred examples include a methyl group and an ethyl group. R ¹¹ and R ¹² are each independently a hydrogen atom, a nitro group, a carboxyl group, shea Anomoto, alkyl group, Ji丄~ヽport alkyl group, a (~ Ji alkoxy) carbonyl group or one COR ^39.

Among such R ¹¹ and R ¹² , preferred is a hydrogen atom. ～〇 Anorekinore group, can be exemplified 〇 ₁ ～〇 ₄ C port alkyl and (CC alkoxy) carbonyl group, as more preferable, a hydrogen atom and. And ₄ alkyl groups.

R ¹³ is a hydrogen atom, a Ci Cs alkyl group, -Represents a haloalkyl group or a substituted or unsubstituted fluoro group.

If having the phenyl group is a substituent, as the substituent, for example, a halogen atom, a nitro group, a carboxyl group, Shiano group, Ci C alkyl group, Ci～C ₄ haloalkyl group, CC alkoxy group, Ci C haloalkoxyl group , (Ci

To c ₄ Anorekokishi) carbonyl group, C alkylthio group, and preferably one or two groups selected from among Ci～C ₄ alkyl sulfinyl group and C alkylsulfonyl group.

Among such R ¹³ , a hydrogen atom, a C Ce alkyl group, or a halogen atom, a C 1 to C ₄ alkyl group and a C 1 to C ₄ alkoxyl group are preferable. Examples thereof include a phenyl group which may be substituted with a group, and more preferable examples include a hydrogen atom and a CiC alkyl group.

R ¹⁴ represents a hydrogen atom, a halogen atom, an alkyl group or a haloalkyl group.

Preferred examples of R ¹⁴ include a hydrogen atom and an alkyl group, and more preferred examples include a hydrogen atom and a methyl group.

R ^{15 to} R ²³ , R ²⁶ and R ²⁷ each represent a hydrogen atom, a halogen atom, a Ci C alkyl group or a C ₁ to C ₄ alkyl group. Among these, as a preferable, a hydrogen atom, can be a halogen atom and Ci～C ₄ alkyl group, more preferred are an be mentioned hydrogen atom, a chlorine atom and a methyl group Wear.

R ²⁴ and R ²⁵ each represent a hydrogen atom, a halogen atom, a CL to C ₄ alkyl group, a C i to C ₄ haloalkyl group, a 〇 to アルコキシ alkoxyl group, a C i to C ₄ haloalkoxyl group ^ / boxyl group, ( shown ci C alkoxy) carbonyl group, Ci C alkylthio group, C} ～〇 ₄ alkylsulfide El group, C I～C ₄ alkylsulfonyl group, amino group, a mono (~. alkyl) amino group or a di alkyl) amino group .

Among such R ²⁴ and R ²⁵ , preferred are a hydrogen atom, a halogen atom, an alkyl group,

It can be exemplified haloalkyl groups and Ci～C ₄ alkoxyl group, and more preferred are, there may be mentioned a hydrogen atom, a chlorine atom, methylation group and main butoxy group. /

R ²⁸ , R ²⁹ and R ^{31 to} R ³⁴ are each a hydrogen atom, a halogen atom,. ~. It represents an alkyl group or C i to C 2, and an alkyl group. Among them, preferred are a hydrogen atom and an alkyl group, and more preferred are a hydrogen atom and a methyl group.

R ³⁵ and R ³⁶ are each independently a hydrogen atom, a halogen atom, N RI 'c ₄ Al kill groups, C ～〇, mouth alkyl groups, C ₁ -C _4, or R ³ ⁵ illustrates an alkoxyl group, R ³⁶ and the carbon atom to which they are attached, together form the formula:

, 9, —

ヽ R ¹³

May be formed.

Preferred examples of R ³⁵ and R ³⁶ include a hydrogen atom. And an alkyl group, a C i -C ₄ alkoxyl group and R ³⁵ , R ³⁶ and the carbon atom to which they are bonded together, having the formula: R ¹⁰

And more preferably a hydrogen atom, a methyl group, an ethyl group, or R ³⁵ , R ³⁶ and the carbon atom to which they are bonded together , Formula:

H ₃ CO ヽ CH ₃

NN ³

II II

And those forming a group represented by C \ or.

R ³⁰ , R ³⁷ , R ³⁸ and R ^{4 (5} each represents a hydrogen atom or a Ci C alkyl group. Of these, preferred are a hydrogen atom, a methyl group and an ethyl group.

R ³⁹ represents a C ₄ -C ₄ alkyl group, a C i -C ₄ alkyl group or a substituted or unsubstituted phenyl group. Here, if the full alkenyl group has a substituent, is to this substituent include a halogen atom, a nitro group, a carboxyl group, Shiano group, 〇～〇 ₄ alkyl group, C I～C, mouth alkyl group, . 1 or 2 selected from the group consisting of: an alkoxyl group, a C ₁ -C ₄ halanolecoxyl group, a (di-alkoxy) carbonyl group, a CC alkylthio group, a C alkylsulfiel group and a C i -C ₄ alkylsulfonyl group. Groups can be mentioned preferably.

Among such R ³⁹ , preferred are a C ₁ -C ₄ alkyl group, Cj-

A C ₄ haloalkyl group or a phenyl group which may be substituted with one or two groups selected from a halogen atom, a C ₁ -C ₄ alkyl group and a CC alkoxyl group, and more preferred. Examples thereof include alkyl groups.

Among the various groups, in one or two Ci～C ₆ chain alkyl group or a C ₃ which is interrupted by oxygen and / or sulfur atoms -C ₆ cyclic alkyl group, C _t ~ Examples of C ₆ alkyl groups (chain) are of the formula: — CH ₂ X ⁸ CH ₃ , —CH ₂ X ⁸ CH ₂ CH ₃ , — CH ₂ X ⁸ CH ₂ CH ₂ CH ₃ , — CH ₂ CH ₂ X ⁸ CH ₃ , — CH ₂ CH ₂ X ⁸ CH ₂ CH ₃ , -CH (CH ₃ ) X ⁸ CH ₂ CH ₃ , -CH ₂ X ⁸ CH (CH ₃ ) ₂ , —CH ₂ X ⁸ C (CH ₃ ) ₃ , -CH ₂ X ⁸ CH (CH ₂ CH ₃ ) ₂ , -CH ₂ X ⁸ CH ₂ CH ₂ X ⁹ CH ₃ , -CH ₂ X ⁸ CH ₂ CH ₂ X ⁹ CH ₂ CH ₃ , One CH ₂ X ⁸ CH ₂ CH ₂ X ⁹ A group represented by CH (CH ₃ ) ₂ can be exemplified. Further, one or two are interrupted by an oxygen atom and or a sulfur atom, and in the C ~ Ji ₆ chain alkyl group or a C ₃ -C ₆ cyclic alkyl group having a halogen atom, C ~ C ₆ haloalkyl group As the (chain), for example, one or two oxygen atoms and / or one or more hydrogen atoms of a C Ce alkyl group (chain) interrupted by a sulfur atom may be replaced by a halogen atom. Specific examples thereof include those substituted with a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

Further, in one or two C ₁ ~ ₆ chain Arukiru group or interrupted by an oxygen atom and Z or a sulfur atom 〇 ₃ ～〇 ₆ cyclic Arukiru group, examples of 〇 _{_3-6} Shikuroaru Kill group As the formula:

And the like.

X ⁸ and X ⁹ each represent an oxygen atom or a sulfur atom. In the case of a sulfur atom, they are partially oxidized to sulfoxide (so) or completely oxidized to sulfon (so ₂ ). You may.

n represents 0 or 1, m, p and q represent 0, 1 or 2, respectively. When p is 2, two R ²⁴ may be the same or different, and when q is 2. And the two R ⁶ may be the same or different. The above m is preferably 2, and p and q are each preferably 0 or 1.

Preferred among the pyrazole derivatives represented by the general formula (I) are those represented by the general formula (I-a)

(Wherein, Q, R ¹ ! ^ ⁶ , X ¹ , X, Y, Z, k, and q are the same as those described above).

The compound represented by the above general formula (I-a) corresponds to R ^{5 of} a benzene ring. It has a structure in which a pyrazolyl group is bonded at the first position via ¹ C (= X ¹ ). In this general formula (I-a), X is a formula

Ten

R

—

(Wherein R ⁷ , R ⁸ and R ^{1 Q} are the same as above), and Y is a group represented by the formula

28

RR ² ° R ³¹

— C or C- C

29 32

R: R ²⁹ R '

Wherein R ²⁸ , R ²⁹ , R ³¹ and R ³² are as defined above, and Z is a group represented by the formula

― S―

(Wherein, m is the same as defined above) is particularly preferable.

Such compounds include the general formula (I-b), the general formula (I_c), the general formula (I-d) or the general formula (I-e)

^{(Wherein, Q,! ^ 1 ~!} ^ 8, R 10, R 28, R 29, R 31, R 32, X 1, k, m and q are as defined above) a compound represented by Can be mentioned.

In the case of a compound capable of forming a salt among the pyrazole derivatives represented by the general formula (I), the salt is also included in the pyrazole derivative of the present invention. The virazole derivative of the present invention does not cause harm to field cultivated crops such as corn, has excellent herbicidal activity, and can control a wide range of field weeds at a low dose.

Next, a method for producing the pyrazole derivative of the present invention represented by the general formula (I) will be described.

The pyrazole derivative, for example, the compound represented by the general formula (1 ′) in which X ¹ in the general formula (I) is an oxygen atom is represented by the following reaction formula

Halogen ^{(wherein, Q, 1 ^ ~11 6,} X, Y, Z, k and q are same as that defined above) as shown in, pyrazole derivative of the general formula (II) (III) It can be produced by a method of reacting a compound (Method A) and a method of reacting a pyrazole derivative of the general formula (II) with an alcohol of the general formula (IV) (Method B).

Method A:

In this method, a virazole derivative of the general formula (II) is reacted with a halogenic compound of the general formula (III) in an inert solvent in the presence of a hydrogen halide scavenger to obtain a compound of the general formula A compound represented by (I ') is produced. In this reaction, the halogen compound of the general formula (II) is preferably used in a proportion of generally 1 to 3 mol per 1 mol of the virazole derivative of the general formula (II). As the hydrogen halide scavenger, for example, bases such as sodium carbonate, potassium carbonate, triethylamine and pyridine are used. These hydrogen halide scavengers are preferably used in an equimolar ratio or more with respect to the compound of the general formula (II), and the reaction temperature is preferably in a range from room temperature to the boiling point of the solvent used. . Examples of the inert solvent include aromatic hydrocarbons such as benzene and toluene, ethers such as getyl ether, ketones such as methylethyl ketone, and halogenated hydrocarbons such as dichloromethane, chlorohonolem, and dichloroethane.

Method B:

In this method, azodicarboxylic acid diester, By reacting the pyrazole derivative of the general formula (II) with the alcohol of the general formula (IV) in the presence of a dehydrating condensing agent such as triffeine phosphine, the compound represented by the general formula () is produced. . In this reaction, the alcohol of the general formula (IV) is preferably used in a proportion of generally 1 to 2 mol per 1 mol of the birazol derivative of the general formula (II). The reaction temperature is preferably in the range from room temperature to the boiling point of the solvent used. Examples of the inert solvent include, for example, aromatic hydrocarbons such as benzene and toluene, ethers such as jetinole ether, halogenated hydrocarbons such as dichloromethane, chloropho / rem, and dichloroethane.

The compound represented by the general formula (Γ ′) wherein X ¹ in the general formula (I) is a sulfur atom is represented by the following reaction formula

Lawesson Reagent

(I ")

'R ⁶ , X, As described above, it can be synthesized by reacting the compound represented by the general formula () with Lawesson's reagent in an inert solvent. The Lawesson reagent is generally preferably used in an amount of 0.5 to 1 mol based on the pyrazonole derivative (I '). The reaction temperature is preferably in the range from room temperature to the boiling point of the solvent used. Examples of the solvent used in the reaction include aromatic hydrocarbons such as benzene and toluene, and ethers such as dimethyl ether and dimethoxyethane.

The pyrazole derivative represented by the general formula (II) can be prepared by a known method (for example, WO93 / 18031, WO94 / 01431, WO95 / 4054, W096 / 25412, W095 / 13275,

WO96 / 30368, WO96 / 31507, WO97 / 12885, WO97 / 19087, WO97 / 42185, WO97 / 01550, WO97 / 03045, WO97 / 08164, W098 / 28291, WO97 / 30986,

WO97 / 30993, WO98 / 12180, WO98 / 12192, W098 / 49159, W098 / 35954, JP-A-7-291970, JP-A-7-316149, USP5607898, USP5631210, USP5723411, USP5885936, DE4427996, DE4427997, DE19527912, etc.) can do.

The herbicide of the present invention contains the pyrazole derivative of the present invention represented by the general formula (I) and / or a salt thereof as an active ingredient, and comprises a compound such as a liquid carrier such as a solvent or a fine powder of a mineral substance. It can be used in the form of a wettable powder, emulsion, powder, granule, etc. by mixing with a solid carrier such as In order to provide emulsifying, dispersing and spreading properties during formulation, a surfactant must be added.

When the herbicide of the present invention is used in the form of a wettable powder, the pyrazole derivative of the present invention and Z or a salt thereof are usually 10 to 55% by weight, and the solid carrier is 40 to 88% by weight. /. A surfactant may be blended at a ratio of 2 to 5% by weight to prepare a composition, which may be used. When used in the form of an emulsion, the pyrazole derivative of the present invention and / or a salt thereof is usually contained in an amount of 20 to 50% by weight, a solid carrier of 35 to 75% by weight, and a surfactant of 5 to 15% by weight. What is necessary is just to mix | blend in a ratio and to prepare a composition. On the other hand, when used in the form of a powder, the pyrazole derivative of the present invention and / or a salt thereof is usually 1 to 15% by weight. / ₀ , a solid carrier may be blended at a ratio of 80 to 97% by weight and a surfactant at a ratio of 2 to 5% by weight to prepare a composition. Further, when used in the form of granules, usually the proportion of the pyrazole derivative of the present invention and / or its salt is 1 to 15% by weight, the solid carrier is 80 to 97% by weight, and the surfactant is 2 to 5% by weight. To prepare a composition. Here, a fine powder of a mineral substance is used as the solid carrier. Examples of the fine powder of the mineral substance include oxides such as kieselguhr, slaked lime, phosphates such as apatite, sulfates such as Secco, tanolek, Pai mouth ferrite, clay, kaolin, bentonite, acid clay, white carbon, quartz powder, and silicates such as calcium stone powder.

Organic solvents are used as the solvent. Specific examples include aromatic hydrocarbons such as benzene, toluene, and xylene; chlorinated hydrocarbons such as 0-chlorotoluene, trichloroethane and trichloroethylene; cyclohexanol; Amanol alcohol, ethylene glycolone, etc., ketones, such as isophorone, cyclohexanone, cyclohexeninole-cyclohexanone, buty cellosenoleb, ethers, such as jeti / letenoleno, methylinoethyl ether, isopropyl acetate, benzyl acetate, phthalic acid Examples include esters such as methyl, amides such as dimethylformamide, and mixtures thereof.

Further, as the surfactant, anionic type (fatty acid salt, alkylsulfate, anolequinolebenzenesnolephonic acid, dianolequinolenesolephosuccinate, anolequinolephosphate phosphate, naphthalene sulfone) can be used. Salts of acid-formalin condensate, polyoxyethylene olenoquinolenosoleate, etc., nonion type (polyoxyethylene alkyl enoate, polyoxyethylene anolequinole pheninoleate enole, polyoxyethylene anolequinoleester) , Polyoxyethylene alkylamine, sorbitan fatty acid ester, polyoxetylene sorbitan fatty acid ester, etc.) and cationic or amphoteric ion type (amino acid, betaine, etc.) can be used.

The herbicide of the present invention may contain, if necessary, other herbicidal active ingredients, together with the pyrazole derivative represented by the above general formula (I), and / or its salt. Such other herbicidally active ingredients include conventionally known herbicides such as phenoxy, diphenyl ether, triazine, urea, carbamate, thiol carbamate, acid anilide, pyrazole, phosphoric acid System, sulfonylurea system, oxaziazone system, etc., and can be used by appropriately selecting from these herbicides.

Furthermore, the herbicide of the present invention can be mixed with an insecticide, a bactericide, a plant growth regulator, a fertilizer, and the like, if necessary.

The herbicide of the present invention is used as a herbicide for upland fields, such as soil treatment, soil mixing treatment, foliage treatment It can be used in any processing method. As the field weeds (Cropland weeds) targeted by the compound of the present invention, for example, Solanaceae weeds, Abutilon theophrasti, and Amebia typified by, for example, Solanum nigrum, Datura stramonium and the like. Convolvulaceae weeds represented by Malvaceae weeds such as Sika spin deer (Sida spinosa), Asagao species (Ipomoea spps.) Such as Malva Asagao (Ipomoea purpurea), and Convolvulaceae represented by Convolvulus (Calystegia spps.). , Amaranthus lividus, etc., Amaranth ace ae, Xanthium strum arium j, Ambrosia artemisiaefolia, Helianthus annus, Gakida cecilia Asteraceae (Compositae) typified by irrigation thistle (Cirsium arvense), Novo-mouth chrysanthemum (Senecio vulgaris), and shrimps (Erigeron annus) ) Weeds, Rorippa indica, Sinapis arvensis, Brassica (Capsellaurea bursa—pastoris) and other cruciferaceae (Cruciferae) weeds. Polygonaceae (Polygonaceae) weeds, Portulaca oleracea (Portulaca oleracea), etc.

(Chenopodium album), Cenopodium ficiiolium, Coleophyllaceae (Chenopodiaceae) weeds such as broom (Kchia scoparia), and Caryophyllaceae weeds such as Hakobe (Stellaria media). Scrophulariaceae weeds, represented by guri (Veronica persica), etc. Weedes, and communis (Commelina communis), etc.

(Commelinaceae) Miscellaneous table, Lamin amplexicaule (Lamium amplexicaule), Lamiaceae (Labiatae) weeds represented by Himeodori Koso (Lamium purpureum), etc. (Euphorbiaceae) weeds, Togenashiyaedara (Galium spurium) Yaemdara (Galium aparine), Akane (Rubia akane), etc., Rakaceae (Rubiaceae) weeds, Violets (Viola arvensis), etc. ) Weeds, Broad-leaved weeds such as legumes (Le uminosae) weeds, such as Sesbania exaltata and Cassia obtusifolia, wild sorghum (Sorgham bicolor), ooo Wedge mill (panicum dichotomiflorum), John Songhus (Sorghum

nalepense), squirrel (Ec inochloa crus-galli) Mehishino (Digitaria adscendens), oats (Avena fatua), ohisino (Eleusine indica), moss (Setaria viridis) Grainaceous weeds, Cyperaceus weeds, Cyperus rotundus, Cyperus esculentus, and the like can be cited.

Further, the compound of the present invention can be used as a herbicide for paddy fields in any of soil treatment and foliage treatment under flooding. Examples of paddy weeds include paddy weeds, such as Herodamodaka (Alisma canaliculatum), Omodaka (Sagittaria trifolia), and Perica (Sagittaria pygmaea).

(Alismataceae) Weeds, Cyperus difformis, Cyperus serotinus, Cynopus juncoides, Eleocharis kuro ^ uwai, and other weeds such as Cyperaceae (Cyperaceae)

(Scrothuslariaceae) weeds, such as (Lindenia pyxidaria), etc., and scrophicaceae, such as oak (Monochoria Vaginalis), etc.

(Potenderiaceae) Weeds, Potamogetonaceae weeds, such as Polgeton distinctus, weeds, and Lythraceae weeds, such as Echinochloa, represented by potamogetonaceae weeds, Rotala indica, etc. And Gramineae weeds.

The effective application amount of the compound of the present invention for weeding can be determined in consideration of various conditions such as the form of the preparation, the application method, the type and amount of the weeds, and the growth condition. Usually, it is 0.001 to 0.3 kg / ha, preferably 0.01 to 0.3 kg / ha, and those skilled in the art can easily determine the effective amount for obtaining the required herbicidal effect.

Next, the present invention will be described in more detail with reference to production examples and herbicide examples. The present invention is not limited to these examples.

Production Reference Example 1 Production of 5-bromomethyl isoxazole

Dissolve 2.0 g (24 mmol) of 5-methylisoxazole in 10 ml of carbon tetrachloride and add 4.5 g (25 mmol) of n-bromosuccinimide (NBS), catalytic amount. 2, 2'-Azobis (isobutyronitrile) (AI BN) plus 8 hours Heated to reflux. The reaction solution was diluted with chloroform, washed with saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 8.5 g (yield 90%) of 5-bromomethyldisoxazoline.

Production Reference Example 23 Production of 3-Chloromethylthiophene

2.0 g (18 mmo 1) of 3-thiophene methanol was dissolved in 20 milliliters of dichloromethane, and 1.9 ml (26 mmo 1) of thiol chloride was added dropwise under ice cooling. After completion of the dropwise addition, the mixture was stirred under ice cooling for 15 minutes, and the solvent was distilled off under reduced pressure to obtain 2.5 g of 3-chloromethylthiophene (97% yield).

Production Example 1

6- (1-Methynole-5-hydroxypyrazole-1-4-inole) Carboninole-5-Methyl-4-methoxyiminothiochroman 1,1 dioxide 0.6 g (1.7 mmo1) was dissolved in 10 ml of acetone. 6 hours after adding 0.43 g (1.8 mmo 1) of 5-bromomethyl isoxazole, 0.27 g (2. Ommo 1) of lithium carbonate, and the amount of tetrabutylammonium iodide catalyst Heated to reflux. The solvent was distilled off, saturated saline was added, and the mixture was extracted with dichloromethane. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue is purified by column chromatography to obtain 6- (1-methyl-5_ (5-isoxazole methinole) oxypyrazolone 4-inole) 0.41 g (54% yield) of chroman 1,1-dioxide (compound 11-1) was obtained.

Production Example 2

6— (1—Ethynolee 5—Hydroxypyrazonole 1—4-inole) Canoleboninole 5—Methyl-4—Methoxyiminothiochroman 1,1 Dioxide 0.6 g (1.6 mmo 1) dissolved in 10 mL of acetone Then, add 0.28 g (1.9 mmo 1) of 3-chloromethylthiophene, 0.29 g (2.1 mmol) of potassium carbonate, and a catalyst amount of tetrabutylammonium iodide, and heat and reflux for 3 hours. did. The solvent was distilled off under reduced pressure, saturated brine was added, and the mixture was extracted with dichloromethane. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by column chromatography to obtain 6_ (1-ethyl-5- (3-thiophene methinole) oxyvirazo-1 / 4- (4-) / re) canoleboninole 5-methinole-1 4-methoxy 0.40 g (yield 51%) of iminothiochroman 1,1-dioxide (compound 2-3) was obtained.

Production Example 3

5- (1- (2-propyl) -1-5-hydroxypyrazole-14-yl) carbo-2-ru 4-cyclomouth _ 2,3-dihydrobenzothiophene 1,1-dioxide 0.50 g (1 . 4mmo 1) was dissolved in toluene 5 ml, Torifueniruho Sufuin 0. 3 7 g (1. 4mmo 1 ), Azokarubon acid Jechiru (40 weight ^_0/0 preparative Ruen solution) 0. 6 1 g (1. 4mxno l), 0.16 g (1.4 mmo 1) of 2-thiophene methanol was added, and the mixture was stirred at room temperature for 24 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The obtained oil was purified by silica gel column chromatography, and the obtained solid was recrystallized from ethanol to give 5- (1- (2-propynole) -1- (2-thiophenemethyl) oxypyrazole. 14-inole) Canolepo 2-ru 41-cloth 1,2,3-dihydrobenzothiophene 1,1-dioxide (compound 1411) 0.18 g (28% yield) was obtained. Was.

Production Example 4

5— (1— (2-propyl) _5—hydroxypyrazonole 4-yl) CARBON NINOLEE 4_CHROME 2,3-dihydrobenzothiophene 1,1-dioxide 0.50 g (1. 4 mmo 1) was dissolved in Tozoreen 5 ml, Torifueniruho Sufuin 0. 3 7 g (1. 4 mm o 1), Azokarubon acid Jechiru (40 weight ^_0/0 preparative Ruen solution) 0.6 1 g (1.4 mmol) and 0.16 g (1.4 mmol) of 3-thiophenmethanol were added, and the mixture was stirred at room temperature for 24 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The obtained oil was purified by silica gel column chromatography, and the obtained solid was recrystallized from ethanol to give 5- (1- (2-p-open-pill) -5- (3-thiophenemethinole) oxypyrazo. 1-ru 4-inole) Canolevo 2-ru 4-chloro-2,3-dihydrobenzothiophene 1,1-dioxide (compound 144-2) 0.23 g (36% yield) was obtained.

The physical properties of the compound of the present invention produced as described above are shown in Tables 1 to 27.

挲 ΐ 建

6ε

O / lOdfAlOd 0016Δ / 10 OAV

If

rezeo / iodr / iDd 0OZ6A / IO OM

Zf

rezco / iodf / iDd 0016UI0 O

Mine

2f

ζεζεο / iodf / iDd 0016./I0 OM Table 5-

ιεζεο / iOdf / iDd 00Z6 mu / 10 O / W Table 5-1

Table 6

^

9f

zezeo / iodf / iDd 0016Z./10 OAV

Table 8

挲 6 粜 zereo / iodf / iDd Table 1 o-

o0 / 1sx:-

υ

挲 s im

Ψ

rei £ o / io <ir / x3d 00Z6./I0 OAV

9S

O / lOdT / 丄 :) d 00Z6L / 10 OM

8S

jezeo / iodf / iDd 00Z6 mu / 10 OAV

Halla 6 ΐ 缉

6S

O / lOdfAIDd 00Z6Z./10 OM Table 21

IR mp Compound No. Yield ¹ ½ NMR (p pm) (cm- ¹ ) (° C)

124 (BH d) 12fifiH, d) 24-42 (4H m)

2.76 (3H, s), 3.8-4.2 (lH, m)

23-1 80 one

4.4-4.7 (lH, m), 5.08 (1H, t), 5.60 (2H, s)

7.1-7.5 (5H, m)

Table 24 D 〇 C

Table 25

Table 26

Table 27

Examples of herbicides

(1) Preparation of herbicide

97 parts by weight of talc as a carrier (trade name: manufactured by G-Cryte, G-Cryte Industries Co., Ltd.), alkylaryl sulfonate as a surfactant (trade name: Neoperex, manufactured by Kao Atlas Co., Ltd.) 1.5 parts by weight and 1.5 parts by weight of nonionic and anionic surfactants (Sonorepol 80 OA, manufactured by Toho Chemical Industry Co., Ltd.) were uniformly pulverized and mixed to obtain a wettable powder carrier.

90 parts by weight of this carrier for wettable powders and 10 parts by weight of the compound of the present invention were uniformly ground and mixed to obtain herbicides. As a herbicide comparative example, the following compounds (A), (B) and (C) were used and prepared in the same manner.

Compounds (A) and (B): compounds described in WO 95/04054

Compound (C): Compound described in W〇96 25412 Compound (A)

Compound (B)

Compound (C)

(2) Criteria for herbicidal effect and crop damage The criteria for herbicidal efficacy and crop damage are:

Residue weight no treatment ratio == (Residue weight of treated area / residual weight of untreated area) X 1 ◦ 0

And applied in the following biological tests. Standard

Herbicidal effect Residue weight untreated ratio (%)

0 8 1 to: L 0 0

6 1 ~ 8 0

2 4 1 to 6 0

3 2 1 ~ 4 0

4 2 0

5 0

Crop injury Residual grass weight untreated ratio (%)

1 0 0

Sat 9 5 ~ 9 9

+ 90-94

+++ 80-89

0-7 9

(3) Biological test (field foliage treatment test)

Weed seeds and corn seeds of Ichibi, Ragweed, Hakobe, Shiroza, Agaeito, Mehishiba and Enokologza are sown in a 1Z500 arel Wagner pot filled with field soil, grown in a greenhouse after covering the soil. And above the 3-4 leaf stage of these plants

A predetermined amount of the herbicide obtained in (1) was suspended in water and sprayed uniformly onto the foliage at a liquid equivalent to 2000 liters / hectare. Thereafter, the plants were grown in a greenhouse and, at 30 days after the treatment, the herbicidal effect and the phytotoxicity to corn were determined according to the criteria of (2). The results are shown in Table 28. Table 28

Note: ga.i.—g active ingredient Table 28 2

Three

Herbicidal effect ¾: 1 ゴ

h 化化物物

No. p'a.i. / Ha

グコ

2-5 100 4 5 5 5 5 5 5 Sat

30 3 5 3 5 3 4 4-

2-6 100 5 5 4 5 5 5 5 Sat

30 3 5 5 5 4 4 3 ―

2-7 100 4 5 5 5 5 5 5-

30 3 5 3 5 4 4 3 1

2-8 100 4 5 5 5 5 5 5-

30 3 5 4 5 4 4 3-

2-9 100 4 5 5 5 5 5 5-

30 3 5 5 5 4 3 3-

2-10 100 5 5 4 5 5 5 4-

30 4 5 3 5 4 3 3-

2-12 100 4 5 4 5 5 5 4-

30 3 5 3 5 4 4 3-

2-13 100 4 5 5 5 5 5 5-

30 3 5 5 5 4 4 3-

3-1 100 5 5 5 5 5 5 5

30 3 4 4 5 5 4 3-

3-2 100 5 5 5 5 5 5 5 Sat

30 3 5 4 5 5 4 3

3-3 100 5 5 5 5 5 5 5 ±

30 3 5 5 5 5 4 4

3-4 100 5 5 5 5 5 5 5

30 3 5 3 4 3 3 3 Table 28 3

Herbicidal effect ;!

Λ ヽヽ / / / メ匕匕匕

Big ぺ The Get Shimo

No g fh a

3-5 100 4 5 5 5 5 5 5-

30 3 5 3 4 4 3 3-

4-1 100 5 5 4 5 5 5 4 ±

30 5 5 3 5 5 4 3-

4-2 100 5 5 5 5 5 5 4-

30 4 5 3 4 4 4 3-

4-3 100 5 5 5 5 5 5 4 1

30 5 5 4 5 4 4 3 1

4-4 100 5 5 5 5 5 5 5 Sat

30 5 5 3 4 3 4 3-

4-5 100 5 5 5 5 5 5 4 1

30 5 5 3 5 4 3 3-

5-1 100 4 5 5 5 5 5 4-

30 3 4 3 4 4 3 3-

5-2 100 5 5 5 5 5 5 5-

30 4 5 4 5 5 4 3 ―

5-3 100 5 5 5 5 5 5 5-

30 4 5 3 5 4 3 4-

5-4 100 5 5 5 5 5 5 4

30 3 5 3 5 4 3 3

5-5 100 5 5 5 5 5 5 5

30 3 5 3 4 4 3 3

5-6 100 5 5 4 5 5 5 5 Sat

30 4 3 3 5 4 3 4 Table 2 8 Table 1 4

a

Herbicidal effect

No. ga.i./ha

ググ

5-7 100 5 5 4 5 5 5 5-

30 4 5 3 5 3 4 3-

5-8 100 5 5 5 5 5 5 5 ―

30 3 5 3 5 4 4 4 ―

5-9 100 5 5 4 5 5 5 5 Sat

30 5 5 3 5 4 4 4-

5-10 100 5 5 4 5 5 5 5-

30 4 5 3 5 4 4 3-

5-11 100 5 5 4 5 5 5 5 Sat

30 5 5 3 5 4 4 3 1

5-12 100 5 5 5 5 5 5 5 Sat

30 5 5 3 5 4 4 3-

5-13 100 5 5 4 5 5 5 5-

30 5 4 3 5 5 3 4 1

6-1 100 5 5 4 5 5 5 4-

30 4 4 3 5 4 3 3-

7-1 100 5 5 5 5 5 5 4 Sat

30 5 5 3 5 5 3 3-

7-2 100 5 5 4 5 5 5 4

30 3 5 3 5 5 4 3

7-3 100 5 5 5 5 5 5 4

30 4 5 3 5 5 4 3

8-1 100 5 5 5 5 5 5 5

30 5 5 4 5 4 4 5 Table 2 8 Table 1 5

Herbicidal effect

Go,

. ノ ha ha ha ha ゲゲ ha ゲゲゲゲゲゲ ha ゲ ha ゲザゲ

1 no y -2 100 5 5 4 5 5 5 4 1

30 3 5 3 5 4 4 3 --3 100 5 5 4 5 5 5 5-

30 5 5 3 5 4 4 5 --4 100 5 5 4 5 5 5 5-

30 5 5 3 5 4 4 5 1-5 100 5 5 5 5 5 5 5-

30 3 5 4 5 4 4 4 --6 100 5 5 4 5 5 5 5 Sat

30 5 5 3 5 4 3 4 --7 100 5 5 4 5 5 5 4-

30 4 4 3 5 4 4 3--3 100 5 5 5 5 5 5 4-

30 3 5 3 5 4 4 3--5 100 5 5 5 5 4 5 4-

30 5 3 3 5 4 4 3--6 100 5 5 5 5 5 5 5 1

30 5 5 5 5 4 3 3 1 -7 100 5 5 5 5 5 5 5 5

30 5 5 5 5 4 3 3-10 100 5 5 4 5 5 5 4

30 4 5 3 5 4 4 3-11 100 5 5 4 5 5 5 4

30 5 5 4 5 4 3 3 Table 28-6

From the results in Table 28, it was confirmed that the herbicide of the present invention does not cause harm to corn and can selectively control a wide range of important upland weeds from monocotyledon to dicotyledon at an extremely low dose. On the other hand, compounds (分かる), (及び) and (C) show poor herbicidal effects.

(4) Biological test (field foliage treatment test 2)

Weed seeds, corn, and wheat of Ichibi, Ragweed, Hakobe, Shiroza, Meishishiba, and Enokorogusa in a 15,000-al arena pot filled with field soil Seeds, after covering the soil, growing in a greenhouse, and suspending a predetermined amount of the herbicide obtained in the above (1) in water at the 3-4 leaf stage of these plants. The spray was evenly applied to the foliage with the liquid volume. Then, the plants were grown in a greenhouse, and on the 30th day after the treatment, the herbicidal effect and the phytotoxicity to corn and wheat were determined according to the criteria of (2). The results are shown in Table 29.

Table 2 9 —

nd = not detected Table 2 9—2

Weeding effect

ヽヽ r r r r ¾ 里-

o.ga.i./ha Sano

Guco

Hatsatsu, no

No -7 100 4 5 3 5 5 5 ― One

30 3 4 2 4 4 3 1 -8 100 5 5 5 5 5 5 1 + +

30 5 5 5 5 5 5 1 + -9 100 5 5 5 5 5 4 1 n.d.

30 5 5 5 5 4 3 1 n.d.-10 100 5 5 5 5 5 5

30 5 4 5 5 5 5 1 + -11 100 5 4 4 5 5 5 1 + +

30 5 3 2 5 5 5 1 + -12 100 5 4 4 5 5 5

30 4 3 2 5 5 5 1 + 3-3 100 5 4 4 5 5 4 1 1

30 3 2 3 4 5 3 ― 1 3-4 100 5 4 5 5 5 4 ― 1

30 3 2 3 4 3 3 ― 1 4-3 100 5 5 5 5 4 4 ― Sat

30 5 5 2 4 3 2

-4 100 5 4 5 5 4 4

30 3 2 2 4 3 2

-1 100 5 5 5 5 5 5 warriors + +

30 4 5 5 5 5 5 + -2 100 5 5 5 5 5 5 Sat + +

30 4 5 5 5 5 4 + Table 2 9-3

From the results in Table 29, it was confirmed that the herbicide of the present invention did not cause phytotoxicity to corn or wheat, and was capable of selectively controlling a wide range of important upland weeds from monocots to dicots at an extremely low dose. Was. In contrast, it can be seen that the compounds (A), (B) and (C) have poor herbicidal effects and poor selectivity for wheat. Industrial applicability

INDUSTRIAL APPLICABILITY The virazole derivative of the present invention does not cause phytotoxicity to field cultivated crops such as corn and can selectively control a wide range of field weeds such as grasses and broadleaf weeds at a low dose. The herbicide of the present invention containing this pyrazole derivative has high performance and is useful not only for agricultural use for controlling upland weeds, but also for non-agricultural use for controlling weeds on non-agricultural lands. is there.

Claims

General formula (I)

Blue

of

[Where X is an oxygen atom or

9

zczeo / iodf / iDd 0OZ6./10 OM

Y is the formula

, 28, 28

— O—, — c-o— — s—, or one c— s—

R ²⁹ R ²⁹

z is an oxygen atom or formula Or

(However, when Z represents a symmetric group, the bond on the left is bonded to the benzene ring, and the bond on the right is bonded to the Y moiety.)

However, the following general formula (V):

When the substituent represented by is bonded to the benzene ring at the meta position with respect to R ⁵ , ζ is not -sο ₂ _.

Υ is the formula

R ³⁰

— Ν—

When X is a group represented by the formula:

R ²⁶

— C = N

It is not a group represented by

Y is the expression

30 p28 p30

~ N— or one C— Ν ·

I

, 29, Z is a group represented by the formula o-s— or

is not a group represented by o ₂ 0 ₂ When Y represents an oxygen atom, X is represented by the formula

R 'R ^2o R ²⁷

— C— or C = C— R ⁸

Wherein z is a group represented by the formula

35

R

C or —— S— represents a group represented by R 36.

When Y represents a sulfur atom, X is represented by the formula

And Z represents a group represented by the formula

X ⁷ R ³⁵

II _π , I

— Represents a group represented by —c— or 1c—.

Q is a condensed or uncondensed with a substituted or unsubstituted naphthyl group or a benzene ring, which may be interrupted by one or two oxygen atoms and / or sulfur atoms, substituted or unsubstituted Containing a C ₃ -C ₆ cycloalkyl group, a c ₄ -c ₆ cycloalkenyl group, or 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur atoms. Alternatively, it represents a substituted or unsubstituted 5- or 6-membered aromatic heterocyclic group which is not condensed, and an ethylene oxide group which may be substituted with a CC alkyl group. The sulfur atom contained in the cycloalkyl and cycloalkenyl groups may be partially or completely oxidized by oxygen.

! ^ And ^ or, each independently represent a hydrogen atom, a halogen atom, C ₁ -C ₄ alkyl or C ~ Ji, showing the mouth alkyl group.

R ³ may be interrupted by a hydrogen atom, one or two oxygen atoms and Z or a sulfur atom, and may have a halogen atom.C Ce chain alkyl group or C _{3 to} C ₆ ring alkyl or C ₂ -C ₆ alkenyl group,, C ₂ -C ₆ Haroaruke alkenyl group, a C ₂ -C ₆ alkynyl group, be the sulfur atom is partially Wakashi Ku by oxygen is fully oxidized Good.

R ⁴ may be interrupted by a hydrogen atom, one or two oxygen atoms and Z or a sulfur atom, and may have a halogen atom, a C _{1 to} C ₆ chain alkyl group, or A C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ haloanolekeninole group, a C ₂ -C ₆ alkyninole group, a cyano group, a carboxyl group or a (Ci- ^ C alkoxy) carbonyl group; May be partially or completely oxidized by oxygen.

R ⁵ may be interrupted by a hydrogen atom, a halogen atom, a nitro group, one or two oxygen atoms and Z or a sulfur atom, and may have a halogen atom. C ₆ chain alkyl group Or a C3-C6 cyclic alkyl group, or a carboxyl group, a cyano group, a thiocyano group, a C alkoxyl group, a C Group, (CC alkoxy) carbonyl group, a mercapto group, Ji ~ Ji alkylthio group, C i~C ₄ alkylsulfide El group, C ₁ -C ₄ alkylsulfonyl group, C ₂ -C ₆ alkenyl group, C ₂ -C ₆ haloalkenyl, or C ₂ -C ₆ shows an alkynyl group, a sulfur atom'm connexion partially or completely oxidized to oxygen contained in the C i~C ₆ chain alkyl group or c ₃ to c ₆ cyclic alkyl group It may be.

R ⁶ may be interrupted by a halogen atom, a nitro group, one or two oxygen atoms and / or a sulfur atom, and may have a halogen atom.Ci-C ₆ chain alkyl group or C ₃ -C ₆ cyclic alkyl group or a carboxyl group, Shiano group, Chioshiano groups, C ～〇 ₄ alkoxyl groups, C ~ C, Roarukokishiru group,

C ₄ alkoxy) carbonyl group, a mercapto group, C i~C ₄ alkylthio group, 〇 ~ C ₄ alkylsulfinyl group, C i~c ₄ alkylsulfonyl group, c ₂ to c ₆ alkenyl Le group, C ₂ -C ₆ halo alkenyl, or C ₂ -C ₆ shows an alkynyl group, a sulfur atom contained in the C -C ₆ chain alkyl group or a C ₃ to c _s cyclic alkyl groups being oxygen Accordingly partially or completely oxidized Is also good.

Xi～X ⁷ is independently an oxygen atom or a sulfur atom.

¹⁷ and ⁸ may each be independently interrupted by a hydrogen atom, a halogen atom, a nitro group, one or two oxygen atoms and / or sulfur atoms, and may have a halogen atom. good ₆ chain alkyl group or a C ₃ -C ₆ cyclic alkyl group or a carboxyl group, Shiano group, C i~C ₄ alkoxyl group. ~ Ji ^! Haroa Rukokishiru group, (Ci~C ₄ alkoxy) carbonyl groups, C I～C ₄ alkylthio groups, C I～C ₄ alkylsulfide el groups, C alkylsulfonyl group, the formula

_CHR ³⁷ N0 _2, one ^{^{^{CHR 37 NR 13 R 14, -}}} CHR 37 P (= 0) (OR 38) 2, - NR 13 R 14, one NR ^³⁷ COR ^39, _NR ³⁷ C_〇 ₂ R ^33, one NR ³⁷ S0 ₂ R ³⁹ , — OCOR ³⁹ , — OCO ₂ R ³⁷ , _OCONR ¹³ R ¹⁴ , — OCHR ³⁷ CN, one O CHR ³⁷ C〇R ³⁹ , one OCHR ³⁷ C〇 ₂ R ³⁸ , one CHR ³⁷ CONR ¹³ R ¹⁴ , one S0 ₂ NR ¹³ R ¹⁴ , —OS〇 ₂ R ³⁹ , —O— N = CR ¹³ R ³⁷ , -P = 0 (OR ³⁸ ) ₂ , -OP = 0 (OR ³⁸ ) ₂ that group, a substituted or unsubstituted phenyl group, Oh Rui represents an aromatic heterocyclic group having 5-membered or 6-membered ring substituted or unsubstituted, the C I～C ₆ chain alkyl group or a C ₃ ~ The sulfur atom contained in the C ₆ cyclic alkyl group may be partially or completely oxidized by oxygen. R ⁹ is a hydrogen atom,

6 alkyl group, C ₁ -C ₆ haloalkyl group, - shows a COR ³⁹ or one S_〇 ₂ R ^39.

R ¹⁰ may be interrupted by a hydrogen atom, one or two oxygen atoms and / or sulfur atoms, and may have a halogen atom.C Ce chain alkyl group or C _{3 to} C ₆ ring alkyl or C ₂ -C ₆ alkenyl group,, C ₂ -C ₆ Haroaru Kenyir group, C ₂ -C ₆ alkynyl group, or the formula: - C_〇_R ^{_{^{39, _C0 2 R 37, -}}} CHR 37 CN, _CHR 37 COR ³⁹ , — CHR ³⁷ C〇 ₂ R ³⁸ , — CHR ³⁷ C ON R ¹³ R ¹⁴ , — CONR ¹³ R ¹⁴ ,-SO _z R ³⁹

Wherein the sulfur atom contained in the C Ce chain alkyl group or the C ₃ -C ₆ cyclic alkyl group may be partially or completely oxidized by oxygen.

R ¹¹ and R ¹² are each independently a hydrogen atom, a nitro group, a carboxyl group, a cyano group, 〇 represents an alkyl group, a C ₄ -C ₄ haloalkyl group, a (CiC anoreoxy) carbonyl group or —COR ³⁹ .

R ¹³ is a hydrogen atom, a C ₁ -C ₆ alkyl group, 〇-. It represents a haloalkyl group or a substituted or unsubstituted phenyl group.

R ¹⁴ represents a hydrogen atom, a halogen atom, Ji ₁ ~ Ji ₄ Arukiru group or 〇 ₁ ～〇 ₄ Haroaruki Honoré group.

R 15 to R ₂₃ , R 26 and R 27 each represent a hydrogen atom, a halogen atom, a Ci CT noralkyl group or a ci to C, or an alkyl group.

R ²⁴ and R ²⁵ each represent a hydrogen atom, a halogen atom, a CiCa alkyl group, a di-C ₄ haloalkyl group, a C-dialkoxyl group, a C i -C ₄ haloalkoxyl group, a carboxyl group, (CCT norrexy) indicating a carbonyl group, C i~C ₄ alkylthio group, Ci～C ₄ alkylsulfide El group, an alkylsulfonyl group, an amino group, a mono (Ci~C ₄ alkyl) amino group or a di (Ci C alkyl) amino group.

R ²⁸ , R ²⁹ and R ^{31 to} R ³⁴ each represent a hydrogen atom, a halogen atom, a C _{1 to} C 47 alkyl group or a C _{1 to} C ₄ alkyl group.

R ³⁵ and R ³⁶ each independently represent a hydrogen atom, a halogen atom, a CiCa alkyl group, a C 1 to haloalkyl group, a C alkoxyl group, or R ³⁵ ,

R ³⁶ and the carbon atom to which they are attached together, form

May be formed.

R ^3Q , R ³⁷ , R ³⁸ and R ^4G each represent a hydrogen atom or a Ci C alkyl group.

, N

1 ³⁹ denotes a 〇 ₁ ～〇 ₄ Arukiru group, 〇 ₁ ～〇 ₄ C port alkyl group or a substituted or unsubstituted phenylene Le group.

k represents the length of the methylene chain and is 0, 1 or 2.

n is 0 or 1.

m, p and q each represent 0, 1 or 2; when p is 2, two R ²⁴ may be the same or different, and when q is 2, two R ⁶ may be the same May be different from each other.].

2 In the general formula (I), when the group represented by Q has a substituent, the substituent may be a halogen atom, a cyano group, a nitro group, a carboxyl group, a hydroxyl group, an amino group, a mono (CiC Alkyl) amino group, di (CiC alkyl) amino group, CiC

₄ alkyl groups, C i C haloalkyl groups, C i -C ₄ alkoxyl groups, haloalkoxyl groups, (CC alkyl) carbonyl groups, (dialkoxy) carbonyl groups, alkylthio groups, C ^ C alkyl sulfier groups and

-C ₄ pyrazole derivative according to claim 1, wherein 1 is a three groups selected from among alkylsulfonyl group.

3 In the general formula (I), when the fuunyl group or the aromatic heterocyclic group for R ⁷ and R ^8, the phenyl group for R ¹³ , and the phenyl group for R ³⁹ have a substituent, the substituent is halogen. Atom, nitro group, carboxyl group, cyano group,

Alkyl group, C to C, alkyl group, alkoxyl group, Ci to C Haloalkoxyl group, (C ₁ -C ₄ alkoxy) carbonyl group, Ci C alkylthio O group, alkylsulfide El group and C ₁ -C ₄ alkylsulfonyl - wherein is from 1 to 3 groups selected from the Le group Item 4. The virazole derivative according to item 1.

4 When the compound of the general formula (I) is

(R ^b ) q

(Wherein, Q, scale ^{^{^{1 ~! ^ 6, X 1}}} , X, Y, Z, k and q, same as is defined above) virazole derivative according to claim 1, wherein the compound table with.

5 In the general formula (Ia), X is

Ten

R

—

Wherein R ⁷ , R ⁸ and R ^{1 Q} are as defined above, and Y is a group represented by the formula

, 28

KR ²⁸ IT ¹

C or C-C

29 32

RR ² "R

(Where R 29

R ²⁸ and R ³¹ and R ³² are the same as defined above), and Z is a group represented by the formula

— S—

The pyrazole derivative according to claim 4, which is a group represented by 0 _m (where m is the same as described above).

6 When the compound represented by the general formula (I-a) is represented by the general formula (I-b), the general formula (I-c), the general formula (I-d) or the general formula (I-e)

(Wherein, Q, scale ^{^{^{1 ~! ^ 8, R 10}}} , R 28 ~R 32, X 1, k, m and q are the are the same as defined above) pyrazole according to claim 4, wherein a compound represented by Derivatives.

7. A herbicide comprising the pyrazole derivative according to claim 1 and Z or a salt thereof as an active ingredient.