WO2008035737A1 - 4-nitrobenzoyl derivative having sulfoxyimino group and herbicide for rice plant - Google Patents

Abstract

Disclosed is a 4-nitrobenzoyl derivative represented by the formula [I] or a salt thereof. Also disclosed is a herbicide for a rice plant, which comprises the derivative or the salt as an active ingredient. (I) wherein R1 represents a halogen atom, an organic group or the like; p represents a number of 1 or the like; R2 and R3 independently represent an alkyl group or the like, or R2 and R3 may together form a 3- to 8-membered hetero ring which may contain 1 to 4 oxygen atoms or the like; and Q represents a group represented by any one of the formulae Q1 to Q8: Q1 Q2 Q3 Q4 Q5 Q6 Q7 Q8 wherein * represents a binding site; G represents an oxygen atom or the like; R4 represents a hydrogen atom or the like; R5 represents a hydrogen atom, an unsubstituted alkyl group, an alkyl group having a substituent or the like; R6 represents a cyano group or the like; R7 represents an alkyl group or the like; R8 to R11 independently represent a hydrogen atom, an alkyl group or the like; X represents a group represented by CH2 or the like; Y represents an oxo group, an alkyl group or the like; and m represents an integer of 0 to 4. It becomes possible to provide a 4-nitrobenzoyl derivative or a salt thereof which can be synthesized in an industrially advantageous manner, can surely exert its efficacy at a lower dose, is highly safe and is useful as an active ingredient for a herbicide for a rice plant, and also provide a herbicide for a rice plant which comprises the compound as an active ingredient.

Description

 Specification

 4-12 trobenzoyl derivative having sulfoxymino group and herbicide for paddy rice

 Technical field

 [0001] The present invention relates to a 4-12 trobenzoyl derivative having a sulfoximino group or a salt thereof, and a herbicide for paddy rice containing one or more of these compounds as active ingredients.

 This application (together with priority based on Japanese Patent Application No. 2006-256434 filed on September 21, 2006 and Japanese Patent Application No. 2007-022495 filed in Japan on January 31, 2007, The content of this is incorporated herein by reference.

 Background art

 [0002] In the cultivation of paddy rice, many herbicides have come to be used for weed control, which has required a great deal of labor. However, since it causes chemical damage to rice, remains in the environment, or pollutes the environment, it is desired to develop a drug that can be used effectively and safely at lower doses.

 [0003] It has been described in several patent literatures that benzoic acid derivatives similar to the compounds of the present invention have herbicidal activity!

[0004] For example, Patent Document 1 describes the ability S that a benzoic acid derivative represented by the following formula is effective as an active ingredient of a herbicide. It is also described that the compounds described in this document are useful as active ingredients in paddy rice herbicides.

[0005] [Chemical 1]

[Wherein Y ′ represents a methyl group, etc., 等 represents a hydrogen atom, etc., X, represents a halogen atom, etc.

, R, R ′ and R ″ each independently represents an alkyl group or the like.)

 However, this document describes the compounds of the present invention! / Nare.

[0007] Patent Document 2 describes that a benzoic acid derivative represented by the following formula is effective as an active ingredient of a herbicide.

[0008] [Chemical 2]

[Wherein, R1 ′ to R5 ′ each independently represents a hydrogen atom or the like, and Q ′ represents the following (Q′—1)

Represents a group or the like represented by ~ (Q'-3).

[0010] [Chemical 3]

(Q '-D (Q'-2) (0 '-3)

[0011] The compounds described in this document broadly include the compounds of the present invention. It is also described that the compounds described in this document contain compounds that show selectivity for rice.

 [0012] However, in this document, only those compounds in which the 4-position of the benzoyl group is a methylsulfonyl group (SOMe) are actually synthesized! Examples,

 2

 Examples are not described.

 [0013] Patent Document 1: Pamphlet of W098 / 42678

 Patent Document 2: WO04 / 052849 Nonfret

 Disclosure of the invention

 Problems to be solved by the invention

[0014] The present invention can be synthesized industrially advantageously, has a low dose and a highly safe and effective safety, and is useful as an active ingredient of paddy rice herbicides. It is an object of the present invention to provide a herbicide for paddy rice containing these compounds as active ingredients.

 Means for solving the problem

 [0015] The present inventors conducted further synthetic development of the compound described as a general formula in Patent Document 2 above. As a result, certain compounds that are conceptually included in the compounds described in Patent Document 2, but are not specifically described in Patent Document 2, are useful as active ingredients in herbicides for paddy rice. As a result, the present invention has been completed.

 That is, the present invention firstly has the formula [I].

[0016] [Chemical 4]

[In the formula, R 1 represents a halogen atom, a hydroxyl group, a mercapto group, an unsubstituted or substituted amino group, a nitro group, or an organic group.

 p represents an integer of 0 to 3. When p is 2 or more, plural R1s may be the same or different.

 R2 and R3 are each independently an unsubstituted or substituted alkyl group, an unsubstituted or substituted cycloalkyl group, an unsubstituted or substituted alkenyl group, an unsubstituted or substituted alkynyl group. Represents an unsubstituted or substituted aryl group, or an unsubstituted or substituted heterocyclic group.

 R2 and R3 are joined together to form a 3- to 8-membered, unsubstituted or substituted heterocycle which may contain 1 to 4 nitrogen, oxygen or sulfur atoms. May be.

 Q represents one selected from groups represented by the following formulas Q1 to Q8.

[0018] [Chemical 5]

 Qi Q2 Q3 Q4

 Q5 Q6 Q7 Q8

(In the formula, * represents a binding site.

 G represents an oxygen atom, a sulfur atom which may be oxidized, or a nitrogen atom which may have a substituent.

 R4 represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted cycloalkyl group, or an unsubstituted or substituted amino group.

 R5 represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkenyl group, an unsubstituted or substituted alkynyl group, an unsubstituted or substituted aryl group, unsubstituted or A substituted heteroaryl group, an unsubstituted or substituted alkylcarbonyl group, an unsubstituted or substituted alkoxycarbonyl group, an unsubstituted or substituted benzoyl group, an unsubstituted or substituted aminocarbonyl group Represents an unsubstituted or substituted alkylsulfonyl group, an unsubstituted or substituted arylsulfonyl group, or an unsubstituted or substituted aminosulfonyl group.

[0020] R6 represents a cyano group, a acetyl group, a group represented by the formula: C = NR7, or a tetrazolyl group having no substituent or a substituent.

R7 represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted alkoxy group. R8 and R9 each independently represents a hydrogen atom or an unsubstituted or substituted alkyl group.

 R10 and R11 each independently represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted cycloalkyl group.

 X represents a group represented by the formula: C (R12) (R13) or a group represented by the formula: NR12.

 R12 and R13 each independently represents a hydrogen atom or an unsubstituted or substituted alkyl group.

 Y represents an oxo group, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted alkoxycarbonyl group.

 m represents 0 /! or any integer.

 When m is 2 or more, a plurality of Y may be the same or different from each other. Y may be bonded to each other to form an unsubstituted or substituted alkylene group. Alternatively, Y and X R12 may combine to form an unsubstituted or substituted alkylene group! /. ] The 4-nitro benzoyl derivative or its salt represented by these is provided.

 [0021] The 4-12 trobenzoyl derivative of the present invention or a salt thereof includes a R1 force halogen atom, an unsubstituted or substituted alkyl group in the formula [I], a formula: —N = S (= 〇) A compound having a group represented by R2R3 (R2 and R3 have the same meaning as described above) is preferable.

 [0022] Secondly, the present invention provides a herbicide for paddy rice containing as an active ingredient one or more of the 4-12 trobenzoyl derivatives or salts thereof of the present invention.

 The invention's effect

 [0023] A composition characterized in that it contains one or two or more of four or twelvetrobenzoyl derivatives having a sulfoximino group of the present invention or a salt thereof as an active ingredient can be synthesized advantageously in an industrially lower manner. It can be used as a herbicide for paddy rice, which is safe and effective at a low dose.

 BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, the present invention will be described in detail.

 1) 4-12 trobenzoyl derivative having a sulfoxymino group or a salt thereof

The first of the present invention is a 4-12 tropenzo having a sulfoximino group represented by the formula (I). Or a salt thereof (hereinafter sometimes referred to as “the compound of the present invention”).

In the above formula (I), R 1 represents a halogen atom, a hydroxyl group, a mercapto group, an unsubstituted or substituted amino group, a nitro group, or an organic group.

 Examples of the halogen atom for R1 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

 [0026] Unsubstituted or substituted amino groups include amino groups; methylamino groups, ethylamino groups, propylamino groups, benzylamino groups, phenylamino groups, 4-chlorophenylamino groups, acetylamino groups, trifluoroacetyl groups. Mono-substituted amino groups such as mino group, benzoylamino group, methyl sulphoninoleamino group, trifluoromethylsulfonylamino group, 4-methylphenylsulfonylamino group; dimethylamino group, jetylamino group, phenylmethylamino group, methylacetyl Examples thereof include di-substituted amino groups such as an amino group, a methylbenzoylamino group, a bis (methylsulfonyl) amino group, a bis (trifluoromethylsulfonyl) amino group, and a bis (phenylsulfonyl) amino group.

 [0027] The organic group means all functional groups containing carbon atoms.

 Examples of the organic group include a cyano group, a formyl group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a haloalkyl group, a haloalkoxy group, an unsubstituted or substituted cycloalkyl group, and an unsubstituted or substituted aryl group. , Unsubstituted or substituted aryloxy group, alkylcarbonyl group, unsubstituted or substituted arylylcarbonyl group, alkoxycarbonyl group, alkylthiocarbonyl group, alkylthio group, alkylsulfenyl group, alkyls, phonyl Groups, unsubstituted or substituted arylthio groups, unsubstituted or substituted arylsulfier groups, unsubstituted or substituted arylsulfonyl groups, and substituted sulfoximino groups. Can be mentioned.

 [0028] Examples of the alkyl group include methyl group, ethyl group, n propyl group, i propyl group, n butyl group, i butyl group, s butyl group, t butyl group, n pentyl group, n hexyl group, etc. An alkyl group of 1 to 6 is preferred).

[0029] The alkenyl group includes an ethyl group, a 1 propenyl group, a 2-propenyl group, a 1-butur group, a 2 butur group, a 3 butur group, a 1-methyl-2-propenyl group, and a 2-methyl group. Nore 2 propenyl group, 1 pentul group, 2 pentur group, 3 pentur group, 4 pentur group, 1-methyl-2-butul group, 2-methyl-2-butur group, 1 hexenyl group, 2 hexenyl group, 3 A hexenyl group, a 4-hexenyl group, a 5-hexenyl group, etc. (an alkenyl group having 2 to 6 carbon atoms is preferred).

[0030] As the alkynyl group, there are an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butyninore group, a 2-buturyl group, a 3-butulyl group, a 1-methyl-2-propynyl group, a 2-methinole-3-buthyl group, a 1-penturyl group, 2-penturyl group, 3-penturyl group, 4-penturyl group, 1-methyl-2-buturyl group, 2-methyl-3-penturyl group, 1-hexynyl group, 1,1 dimethyl-2-buturyl group, etc. The alkynyl group is preferred).

[0031] Examples of the alkoxy group include a methoxy group, an ethoxy radical, n-propoxy, i-propoxy radical, n-butoxy group, i-butoxy group, s-butoxy group, t-butoxy radical, n Penchiruokishi radical, _n - the Kishiruokishi group (carbon And an alkoxy group having a number of 1 to 6 is preferable.

 [0032] The haloalkyl group includes a chloromethyl group, a fluoromethyl group, a bromomethyl group, a dichloromethyl group, a difluoromethyl group, a dibromomethyl group, a trichloromethinole group, a trifluoromethyl group, a 2,2,2-trichlorodiethyl group, 2 , 2, 2-trifluoroethyl group, pentafluoroethyl group and the like (preferably a haloalkyl group having 1 to 6 carbon atoms).

 [0033] The haloalkoxy group includes a chloromethoxy group, a dichloromethoxy group, a trichloromethoxy group, a difluoromethoxy group, a trifluoroleoromethoxy group, a 1 fluoroethoxy group, a 1,1-difluoroethoxy group, and 2, 2, 2 trifluor. And an oxyoxy group (preferably a haloalkoxy group having 1 to 6 carbon atoms).

 [0034] As the cycloalkyl group of the unsubstituted or substituted cycloalkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc. (a cycloalkyl group having 3 to 8 carbon atoms is preferable). )).

[0035] In addition, examples of the substituent of the cycloalkyl group include an alkyl group such as a methyl group, an ethyl group, an npropyl group, and an isopropyl group (preferably an alkyl group having 1 to 6 carbon atoms); a chloromethyl group, a fluoromethyl group , Bromomethyl group, dichloromethyl group, difluoromethyl group, dibu mouth peach chinole group, 卜 chloro methinore group, 卜 ri 卜 no 才 才 メ チ 2, 2, 2, 2, 2- 卜 chloro chinenore group, 2 , 2, 2 A haloalkyl group having 1 to 6 carbon atoms (preferably a haloalkyl group having 1 to 6 carbon atoms) such as a trifluoroethyl group or a pentafluoroethyl group; a methoxy group, an ethoxy group, or an n-type group Alkoxy groups such as a poxy group and an isopropoxy group (preferably an alkoxy group having 1 to 6 carbon atoms); a hydroxy group; a nitro group; a cyan group; an amino group; a methoxycarbonyl group, an ethoxycarbonyl group, an n propoxycarbonyl group, Alkoxycarbonyl groups such as isopropoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group (preferably alkoxycarbonyl groups having 2 to 6 carbon atoms); halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; Alkylsulfonyl groups such as methanesulfonyl group, ethylsulfonyl group, n-propylsulfonanol group (preferably Alkylsulfonyl group) having 1 to 6 carbon atoms; and the like.

 In addition, the cycloalkyl groups may be the same or different and may have a plurality of substituents.

 Examples of the aryl group of the unsubstituted or substituted aryl group include a phenyl group, a 1 naphthyl group, a 2 naphthyl group (preferably an aryl group having 6 to 14 carbon atoms).

[0037] Examples of the substituent for the aryl group include those exemplified as the substituent for the cycloalkyl group.

[0038] Examples of the aryloxy group of the unsubstituted or substituted aryloxy group include a phenoxy group, a 1 naphthyloxy group, a 2 naphthyloxy group, etc. (C6-C14, preferably an aryloxy group! /,). It is done.

[0039] Examples of the substituent for the aryloxy group include those exemplified as the substituent for the cycloalkyl group.

[0040] Examples of the alkylcarbonyl group include a acetyl group, propionyl group, bivaloyl group and the like (preferably an alkylcarbonyl group having 2 to 6 carbon atoms).

[0041] The arylylcarbonyl group of the unsubstituted or substituted arylylcarbonyl group includes a phenylcarbonyl group, a 1 naphthylcarbonyl group, a 2-naphthylcarbonyl group, etc. (carbon number 7 to 15; Group is preferred).

[0042] Examples of the substituent of the arylcarbonyl group include the substituent of the cycloalkyl group. The thing similar to what was shown is mentioned.

 [0043] The alkoxycarbonyl group includes a methoxycarbonyl group, an ethoxycarbonyl group, n

 Propoxycanoleponinole group, i propoxycanoleponinole group, n butoxycanoleponinole group, i butoxycarbonyl group, s butoxycarbonyl group, t butoxycarbonyl group, n pentyloxycarbonyl group, n hexyloxycarbonyl Group (an alkoxycarbonyl group having 2 to 6 carbon atoms is preferred).

 [0044] Examples of the alkylthiocarbonyl group include a methylthiocarbonyl group, an ethylthiocarboninole group, an n-propylthiocarbonyl group, an i-propylthiocarbonyl group, an n-butinoretiocarbonyl group, an i-butylthiocarbonyl group, an s-butylthiocarbonyl group, t Butinoreticanorepo 2-nole group, n-pentinoretico-renopinore group, n-hexenoreio-canorepo group, etc. (C2-C6 alkylthiocarbonyl group is preferred! /) .

 [0045] Examples of the alkylthio group include a methylthio group, an ethylthio group, an n-propylthio group, an i-propylthio group, an n-butylthio group, an i-butylthio group, an s-butylthio group, a tert-butylenothio group, and the like (an alkylthio group having 1 to 6 carbon atoms). Are preferred).

 [0046] The alkyl sulfier group includes a methyl sulfier group, an ethyl sulfier group, n

 Propyl sulfiel group, i-propyl sulfiel group, n butyl sulfiel group, i-butyl sulfiel group, s butyl sulfiel group, t-butyl sulfiel group, etc. Preferred).

 [0047] Examples of the alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, an n-type pinolesnorehoninole group, an ipropinoresnorehoninole group, an n-butinolesnorehoninole group, and an i-butinoresulfonyl group. S butylsulfonyl group, t-butylsulfonyl group, etc. (C1-C6 alkylsulfonyl groups are preferred! /).

 [0048] Examples of the arylothio group of the unsubstituted or substituted arylothio group include a phenylthio group, a 1-naphthylthio group, a 2-naphthylthio group, etc. (C6-C14, an arylo group is preferred). It is done.

 [0049] Examples of the substituent for the arylothio group include those exemplified as the substituent for the cycloalkyl group.

[0050] An arylsulfier group of an unsubstituted or substituted arylsulfuryl group and Examples thereof include phenylsulfinyl group, 1 naphthylsulfinyl group, 2-naphthylsulfinyl group and the like (preferably aryl group having 6 to 14 carbon atoms).

 [0051] Examples of the substituent for the arylsulfier group include those exemplified as the substituent for the cycloalkyl group.

 [0052] As the aryl sulfonyl of the unsubstituted or substituted aryl sulfonyl group, the aryl sulfonyl group includes a phenyl sulfonyl group, a 1 naphthyl sulfonyl group, a 2 naphthyl sulfonyl group and the like (having 6 to 14 carbon atoms). An arylsulfonyl group is preferred! / ヽ).

 [0053] Examples of the substituent of the arylsulfonyl group include the same substituents as those exemplified as the substituent of the cycloalkyl group.

[0054] The sulfoximino group having a substituent is a group represented by the formula: N = S (◯) (rl) (r2), wherein rl and r2 are each independently R2 and R3 described later. Examples similar to those illustrated as specific examples of these are mentioned.

 Also, rl and r2 join together to form a ring! /

 Specific examples of the sulfoximino group having a substituent include the following.

[0055] [Chemical 6

[0056] Among these, R1 represents a halogen atom, an alkyl group having 1 to 6 carbon atoms, or a carbon number of 1 A halogen atom, preferably at least one selected from the group consisting of ˜6 haloalkyl groups, C 1-6 alkoxy groups, C 1-6 haloalkoxy groups, and C 3-6 cycloalkyl groups A haloalkyl group having 1 to 6 carbon atoms is more preferable.

 [0057] R2 and R3 each independently represents an unsubstituted or substituted alkyl group, an unsubstituted or substituted cycloalkyl group, an unsubstituted or substituted alkenyl group, an unsubstituted or substituted group. An alkynyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted heterocyclic group.

 [0058] R2 and R3, unsubstituted or substituted (alkyl group, cycloalkyl group, alkenyl group, alkynyl group, aryl group), an alkenoquinole group, cycloalkyl group, alkenyl group, alkynyl group, aryl group. Preferable specific examples of the group include the same groups as those exemplified as the alkyl group, cycloalkyl group, alkenyl group, alkynyl group and aryl group of R1.

 [0059] Examples of the substituent for the anorequinole group, alkenyl group, and alkynyl group of R2 and R3 include halogen atoms such as fluorine atom, chlorine atom, bromine atom; and those having 1 to 6 carbon atoms such as methoxy group and ethoxy group Alkoxy group; alkylthio group having 1 to 6 carbon atoms such as methylthio group and ethylthio group; alkylsulfoninol group having 1 to 6 carbon atoms such as methylsulfonyl group and ethylsulfonyl group; And a phenylsulfonyl group having no substituent or a substituent, such as a norefinenoresnorephoninore group and a 2-chlorophenenoresulphonyl group.

 In addition, the alkyl group, alkenyl group, and alkynyl group of R2 and R3 may have the same or different substituents.

 Examples of the substituent for the cycloalkyl group and aryl group of R2 and R3 include those exemplified as the substituent for the cycloalkyl group of R1.

[0060] Examples of the heterocyclic group of the unsubstituted or substituted heterocyclic group represented by R2 and R3 include 2-furinole group, 3 frinole group, 2 cheninole group, 3 cheninole group, 2 year old xazozo ' Linole, 2-oxazolinyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3 isoxazolinyl, 2 thiazolyl, 2 thiazolinyl, 3 isothiazolyl, 3 isothiazolinyl, 2 biranyl Group, 4-tetrahydroviranyl group, 1 Azetidyl group, 2 azetidyl group, 3 azetidyl group, 2 pyrrolyl group, 2 pyrrolidinino group, 2 imidazolinol group, 3 pyrazolyl group, 2 imidazolininole group, 2 pyridyl group, 3 pyridinore group, 4 pyridinore group, 2 piperidinore group 2 monoreforinyl group, monoreforino group, 2 piperazinyl group, 2 pyrimigenole group, 3 pyridazinyl group, 2-pyrazuryl group and the like.

 [0061] Examples of the substituent of the heterocyclic group include alkyl groups such as a methyl group, an ethyl group, an npropyl group, and an isopropyl group (preferably an alkyl group having 1 to 6 carbon atoms); a chloromethyl group and a fluoromethyl group. , Bromomethyl group, dichloromethyl group, difluoromethyl group, dibu-mouthed momethinole group, 卜 lichloromethinole group, 卜 lifunore rometinore group, 2, 2, 2- 卜 lichloroethinole group, 2, 2, 2-trifnoleoloetinole group, A haloalkyl group such as a pentafluoroethyl group (preferably a haloalkyl group having from 6 to 6 carbon atoms); an alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group or an isopropoxy group (preferably having a carbon number of 1 to 6); Hydroxy group; nitro group; cyano group; amino group; methoxycarbonyl group, ethoxycarbonyl group, n propoxycarbonyl group Alkoxycarbonyl groups such as isopropoxycarbonyl group, n-butoxycarbonyl group, and t-butoxycarbonyl group (preferably alkoxycarbonyl groups having 2 to 6 carbon atoms); halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom Or an alkenoquinolesulfonyl group (preferably an alkylsulfonyl group having 1 to 6 carbon atoms) such as a methinolesnorehoninore group, an ethinoresnorehoninore group, or an n-propinoresnorehoninore group; .

 [0062] Further, R2 and R3 are bonded together, and may contain 1 to 4 nitrogen atoms, oxygen atoms, or sulfur atoms in addition to sulfur atoms. Or you may form the heterocyclic ring which has a substituent! / ヽ.

 [0063] Examples of the heterocycle include a thiophene ring, a tetrahydrothiophene ring, a thiopyran ring, a tetrahydrothiopyran ring, a 4-oxanthian ring, a thiomorpholine ring, a 1,4-dithiane ring, a tetrahydrothiopyran 4 on ring, and the like. Is mentioned.

 [0064] Q represents one selected from groups represented by the following formulas Q1 to Q8.

[0065] [Chemical 7]

 Q5 Q6 Q7 Q8

[0066] In the above formulas (Q1 to Q8), * represents a binding site.

 G represents an oxygen atom, a sulfur atom that may be oxidized, or a nitrogen atom that may have a substituent.

 Examples of the sulfur atom that may be oxidized include SO— and —SO—.

 2

 [0067] It may have a substituent! /, And the substituent of the nitrogen atom may be an alkyl group such as a methyl group or an ethyl group; an unsubstituted or substituted group such as a phenyl group or a 4 methylphenyl group; And a phenyl group having an acyl group such as a acetyl group or a benzoyl group.

 [0068] R4 represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted cycloalkyl group, or an unsubstituted or substituted amino group.

 [0069] Examples of the unsubstituted or substituted alkyl group, unsubstituted or substituted cycloalkyl group, and unsubstituted or substituted amino group of R4 include unsubstituted or substituted Rl and R2. Specific examples of the alkyl group having a group, the unsubstituted or substituted cycloalkyl group, and the unsubstituted or substituted amino group are the same as those listed.

[0070] R5 is a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkenyl group, an unsubstituted or substituted alkynyl group, an unsubstituted or substituted aryl group, Heteroaryl having no substituent or substituent Group, unsubstituted or substituted alkylcarbonyl group, unsubstituted or substituted alkoxycarbonyl group, unsubstituted or substituted benzoyl group, unsubstituted or substituted aminocarbonyl group, unsubstituted or substituted It represents an alkylsulfonyl group having a group, an unsubstituted or substituted arylsulfonyl group, or an unsubstituted or substituted aminosulfonyl group.

 [0071] Examples of the unsubstituted or substituted alkyl group, unsubstituted or substituted alkenyl group, unsubstituted or substituted alkynyl group, unsubstituted or substituted aryl group of R5 include the aforementioned Specific examples of the unsubstituted or substituted alkyl group, unsubstituted or substituted alkenyl group, unsubstituted or substituted alkynyl group, unsubstituted or substituted aryl group of R1 to R3 The ones listed are the same.

 [0072] The heteroaryl group of the unsubstituted or substituted heteroaryl group includes a phenyl group, a furyl group, a pyrazolyl group, an imidazolyl group, a 1, 2, 4-triazolinole group, a thiazolyl group, an isothiazolyl group, 1, 3 4, 4-thiadiazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, pyridinole group, pyrimidyl group, pyridazinole group, pyrazinole group, S triazinole group, 1, 2, 4 triazinole group and the like.

 [0073] Examples of the substituent of the heteroaryl group include those listed as specific examples of the substituent of the cycloalkyl group of R1.

 [0074] Examples of the unsubstituted or substituted alkylcarbonyl group include a acetyl group, a trifluoroacetyl group, a bivaloyl group (preferably an alkylcarbonyl group having 2 to 6 carbon atoms).

 [0075] Examples of the unsubstituted or substituted alkoxycarbonyl group include a methoxycarbonyl group, a trifluoromethoxycarbonyl group, an ethoxycarbonyl group, an n-propoxy group, an isopropoxycarbonyl group, etc. 2-6 alkoxycarbonyl groups are preferred).

[0076] Examples of the unsubstituted or substituted benzoyl group include a benzoyl group, a 4-chlorobenzoyl group, a 4-methylbenzoyl group, a 3-methoxybenzoyl group, and a 2,4-difluorobenzoyl group. [0077] Examples of the unsubstituted or substituted aminocarbonyl group include an aminocarbonyl group, a methylaminocarbonyl group, an ethylaminocarbonyl group, a benzylaminocarbonyl group, a phenylaminocarbonyl group, and dimethyl Examples thereof include an aminocarbonyl group and a phenylmethylaminocarbonyl group.

 [0078] Examples of the unsubstituted or substituted alkylsulfonyl group include a methylsulfonyl group, a trifunoleolomethylenolesnorehoninore group, an ethenoresnorehoninore group, an n-propinoresnorephoninore group, and the like. It is done.

 [0079] Examples of the unsubstituted or substituted arylsulfonyl group include a phenylsulfonyl group, a 4-methylphenylsulfonyl group, a 1-naphthylsulfonyl group, a 2-naphthylsulfonyl group, and the like.

[0080] Examples of the unsubstituted or substituted aminosulfonyl group include an aminosulfonyl group, a methylaminosulfonyl group, an ethylaminosulfonyl group, a benzylaminosulfonyl group, a phenylaminosulfonyl group, a dimethylaminosulfonyl group, and a phenyl group. Examples thereof include a methylaminosulfonyl group.

[0081] R6 represents a cyano group, a acetyl group, a group represented by the formula: C = NR7, or a tetrazolyl group having an unsubstituted or substituted group.

[0082] Specific examples of the unsubstituted or substituted alkyl group and the unsubstituted or substituted alkoxy group of R7 include the unsubstituted or substituted alkyl group of R1, unsubstituted or substituted. Specific examples of the alkoxy group having a group are the same as those listed.

[0083] R8 and R9 each independently represent a hydrogen atom or an unsubstituted or substituted alkyl group.

 Specific examples of the unsubstituted or substituted alkyl group for R8 and R9 include the same as those listed as specific examples of the unsubstituted or substituted alkyl group for R1.

 [0084] R10 and R11 each independently represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted cycloalkyl group.

R10 and R11 are unsubstituted or substituted alkyl groups, unsubstituted or substituted. Specific examples of the cycloalkyl group having a substituent are the same as those listed as specific examples of the unsubstituted or substituted alkyl group of R1 and the unsubstituted or substituted cycloalkyl group. It is done.

[0085] X represents a group represented by the formula: C (R12) (R13) or a group represented by the formula: NR12.

 Here, R12 and R13 each independently represent a hydrogen atom or an unsubstituted or substituted alkyl group.

 Specific examples of the unsubstituted or substituted alkyl group for R12 and R13 include the same as those listed as specific examples of the unsubstituted or substituted alkyl group for R1.

[0086] Y represents an oxo group (= 0), an unsubstituted or substituted alkyl group, or an unsubstituted or substituted alkoxycarbonyl group.

Specific examples of the unsubstituted or substituted alkyl group for Y include the same force S as listed as specific examples of the unsubstituted or substituted alkyl group for R1. Specific examples of the unsubstituted or substituted alkoxycarbonyl group for Y include the same as those listed as specific examples of the unsubstituted or substituted alkoxycarbonyl group for R5. .

[0088] m represents an integer of 0 to 4.

 When m is 2 or more, a plurality of Y may be the same or different from each other. Y may be bonded to each other to form a hydrogen atom, an unsubstituted or substituted alkylene group. . In addition, Y and R12 of X may bond to each other to form an unsubstituted or substituted alkylene group.

 [0089] Specific examples of the unsubstituted or substituted alkylene group include 0 to 3 nitrogen atoms, oxygen atoms, or sulfur atoms as shown below, and an alkylene chain having! To 6 carbon atoms. 3-8 membered spiro ring represented by the following (Q2-1), 3-8 membered condensed ring represented by the following (Q2-2), 3-8 represented by the following (Q2-3) Membered bridged rings and the like.

[0090] [Chemical 8]

Q2-1 Q2-2 Q2-3

[In the formula, G, R5 and X represent the same meaning as described above, and Z represents an alkylene chain having 1 to 6 carbon atoms containing 0 to 3 nitrogen atoms, oxygen atoms and / or sulfur atoms. )

 From the viewpoint of having excellent herbicidal activity, the 4 nitrobenzoyl derivative of the present invention is represented by the following formula (I a)

 [0093] [Chemical 9

[0094] (wherein R1 to R3, p, and Q represent the same meaning as described above) are preferable.

, The following formula (I b)

[0095] [Chemical 10]

[0096] (wherein R1 to R3, and Q have the same meaning as described above) are more preferable.

 The 4-nitrobenzoyl derivative of the present invention or a salt thereof is a compound of the group represented by R1 in the formula (I-b), which is a halogen atom, an unsubstituted or substituted alkyl group. Is more preferable.

 In the 4-nitrobenzoyl derivative of the present invention or a salt thereof, R1 is more preferably a compound having a group represented by a chlorine atom, CH3 or CF3 in the formula (I-b).

(Method for producing compound of the present invention)

 The compound of the present invention can be produced by a known method. An example of the method for producing the compound of the present invention is shown below.

In the compound of the present invention, in the formula (I), Q is a compound represented by Ql, Q2 or Q3, R5 is a hydrogen atom, and G is an oxygen atom. It can be manufactured by the method shown in the following.

[0099] [Chemical 11]

 (I-Qla)

[Wherein R1 to R4, R7 and p represent the same meaning as described above, and T represents a leaving group such as a halogen atom or an imidazolyl group.]

[0101] First, a benzoic acid compound represented by the formula (III) is reacted with a halogenating agent such as thioylucyl chloride, oxalyl chloride, or carbonyldiimidazoles, and then represented by the formula (Π). To obtain a compound.

 [0102] This reaction is preferably carried out in an organic solvent. The organic solvent to be used is not particularly limited as long as it is inert to the reaction, for example, aromatic hydrocarbons such as benzene and toluene; halogen hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride; Nitriles such as acetonitryl; and the like.

The reaction temperature is usually from 0 ° C to 120 ° C, and the reaction time is usually from several minutes to several hours. [0103] Next, the compound represented by the formula (II Qla) is obtained by allowing the compound represented by the formula (Qla) to act on this compound in an organic solvent in the presence of a base.

[0104] Examples of the base used include amines such as triethylamine and pyridine.

 Examples of the organic solvent to be used include the same organic solvents listed as the organic solvent used in the reaction for producing the compound represented by the above formula (Π).

 The reaction temperature is usually from 20 ° C to + 120 ° C, and the reaction time is usually from several minutes to several hours.

 [0105] Next, the obtained compound represented by the formula (II Qla) is subjected to a rearrangement reaction in an organic solvent using a cyan source and a base group, thereby being represented by the target formula (I Qla). Obtain power S to get compounds.

 [0106] Examples of the cyan source to be used include acetone cyanohydrin, potassium cyanide, sodium cyanide and the like. The amount of the cyan source used is usually 0.01 to;! Equivalent to the compound represented by the formula (II Qla).

[0107] Examples of the base to be used include triethylamine, diisopropylethylamine, pyridine and the like. The amount of the base used is generally 0.0; for the compound represented by the formula (II Qla);

1 equivalent.

 [0108] The organic solvent to be used is not particularly limited as long as it is inert to the reaction. For example, aromatic hydrocarbons such as benzene and toluene; halogen hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride. Nitriles such as acetonitrile; esters such as ethyl acetate

And the like.

 The reaction temperature is usually from 0 ° C to 120 ° C, and the reaction time is usually from several minutes to several days.

Similarly, as represented by the following formula, by reacting the compound represented by the formula (II) with a compound represented by the formula (Q2a) or (Q3a), the corresponding formula (II By obtaining a compound represented by Q2) or (II Q3) and subjecting this compound to a rearrangement reaction using a cyan source and a base, they are represented by the corresponding formulas (IQ 2a) and (IQ 3a), respectively. Use the power S to obtain the target compound.

[0110] [Chemical 12]

 (I-Q3a)

[In the formula, R1 to R3, R8, R9, Y, m, X and p represent the same meaning as described above.]

 In the compound of the present invention, in the formula (I), Q is a compound represented by the above-mentioned Ql, Q2, Q3

In Ql, Q2 and Q3, a compound in which R5 is a group other than a hydrogen atom and G is an oxygen atom can be produced by the method shown below.

[0112] [Chemical 13]

 (I-02b)

 (I-Q3a)

 (I-Q3b)

[Wherein R1 to R5, R7 to R9, X, Y, p and m represent the same meaning as described above, W represents a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom; A sulfonoxy group such as a sulfonyloxy group, p-toluenesulfonyloxy group, and trifluoromethanesulfonyloxy group; a leaving group such as an acyloxy group such as an acetoxy group and a benzoyloxy group;

 [0114] That is, reacting a compound represented by the formula (I Qla), (I Q2a) or (I Q3a) with a compound represented by the formula: R5-W in an organic solvent in the presence of a base. The force S for producing the target compounds represented by the formulas (I Qlb), (I Q2b) and (I Q3b), respectively, is divided by

[0115] The organic solvent used in this reaction is not particularly limited as long as it is inert to the reaction. For example, amides such as dimethylformamide (DMF); tetrahydrofuran (THF), di Ethers such as oxane; aromatic hydrocarbons such as toluene and benzene; and the like

[0116] Examples of the base used include metal hydrides such as sodium hydride, potassium hydride and calcium hydride; metal alkoxides such as potassium t-butoxide; alkali metals such as lithium and sodium; alkaline earth metals such as magnesium. Metal hydroxides such as sodium hydroxide, lithium hydroxide, calcium hydroxide, etc .; organic bases such as triethylamine, pyridine;

 [0117] The reaction temperature is usually from -50 ° C to + 120 ° C, and the reaction time is usually from several minutes to several hours.

 [0118] In the compound of the present invention, in formula (I), Q is a compound represented by Ql, Q2, or Q3. In Ql, Q2, or Q3, R5 is a group other than a hydrogen atom, and G is sulfur. A compound that is an atom can be produced by the following method.

[0119] [Chemical 14]

 I-Q1C) (I-Qld)

 (I-Q2c)

 (I-Q2d)

 (I-Q3c)

 (I-Q3d)

[In the formula, R1 to R5, R7 to R9, X, W, Y, p and m represent the same meaning as described above.]

 That is, a compound represented by the formula (I Qla), (I Q2a) or (I Q3a) is sulfonylated or halogenated in a suitable organic solvent in the presence of a base to give a compound of the formula (I Qlc) (I Q2c) or a compound represented by the formula (I -Q3c), and then reacting a mercabtan compound represented by the formula: R5—SH in the presence of a base, respectively, The target compounds represented by (I Qld), (I Q2d) and (I Q3d) can be produced.

 [0121] Examples of the reagent used for the sulfonylation include sulfonic acid chlorides such as trifluoromethanesulfuryl chloride; sulfonic acid anhydrides such as trifluoromethanesulfonic acid anhydride; and the like.

Examples of the base to be used include triethylamine, pyridine and the like. [0122] The sulfonylation reaction can be carried out in a suitable organic solvent. The organic solvent to be used is not particularly limited as long as it is inert to the reaction, but amides such as DMF; ethers such as THF; halogenated hydrocarbons such as black mouth form; aromatics such as benzene and toluene. Group hydrocarbons; and the like.

 The reaction temperature is usually from 20 ° C to + 120 ° C, and the reaction time is usually from several minutes to several hours.

 [0123] Further, examples of the halogenating agent to be used include phosphorus pentachloride, phosphorus oxychloride, oxalino chloride, thioyl chloride, thionyl bromide, N chlorosuccinimide, N-promosuccinimide, chlorine, bromine and the like. .

 [0124] The halogenation reaction can be carried out without solvent or in an organic solvent. Examples of the organic solvent to be used include aromatic hydrocarbons such as benzene and toluene; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; ethers such as THF: and the like. The reaction temperature is usually from 10 ° C to + 120 ° C, and the reaction time is usually from several minutes to several hours.

 [0125] Examples of the base used in the reaction of the mercabtan compound include alkali metal hydrides such as sodium hydride and potassium hydride; alkaline earth metal hydrides such as calcium hydride; metals such as potassium t-butoxide. Examples thereof include alkoxides; alkali metals; alkaline earth metals; metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide; organic bases such as tritylamine and pyridine.

 The reaction temperature is usually from 50 ° C to + 120 ° C, and the reaction time is usually from several minutes to several hours.

 [0126] In the compound of the present invention, in the formula (I), the compound which is a group represented by Q force Q4 or Q8 is

Can be produced by the method represented by the following formula.

[0127] [Chemical 15]

[Wherein R1 to R4, R6 and p have the same meaning as described above.]

 That is, by reacting a compound represented by formula (II) with a compound represented by formula (Q4a) or formula (Q8a) in an organic solvent in the presence of a base, The target compound represented by I Q4a) or formula (I Q8a) can be produced.

 [0129] Bases used in this reaction include metal hydrides such as sodium hydride and potassium hydride; metal alkoxides such as potassium tert-butoxide and magnesium ethoxide; metal carbonates such as potassium carbonate; triethylamine and pyridine. Organic bases; and the like.

 [0130] Examples of the organic solvent used in this reaction include ethers such as THF and jetyl ether; amides such as DMF; halogenated hydrocarbons such as methylene chloride and chloroformate; nitriles such as acetonitryl. Aromatic hydrocarbons such as benzene and toluene; The reaction temperature is usually −50 ° C. to + 120 ° C., and the reaction time is usually several minutes to several tens of hours.

 [0131] In the compound of the present invention, in formula (I), a compound in which Q is a group represented by Q6 and G is an oxygen atom can be produced by a method represented by the following formula.

[0132] [Chemical 16]

[Wherein R1 to R3, R10, Rl1 and p represent the same meaning as described above, and R22 represents an alkyl group such as a methylol group, an ethyl group, an npropyl group, an isopropyl group, or a tbutyl group; Benzyl group; or a phenyl group, R23 and R24 each independently represent a hydrogen atom; an alkyl group such as a methyl group or an ethyl group; an alkoxy group such as a methoxy group, an ethoxy group, or an n-propoxy group; Or an amino group which may have a substituent such as an amino group, a dimethylamino group or a jetylamino group, provided that R23 and R24 are not simultaneously an alkyl group or a phenyl group.)

That is, first, with respect to the compound represented by the formula (II) to be used, 1 to 3 equivalents of an acyl acyl ester represented by the formula (V) and 1 to 3 equivalents of a base in an organic solvent. React with metal A salt is prepared, and a compound represented by the formula (II) is reacted therewith to obtain a compound represented by the formula (VI).

 [0135] Examples of the base to be used include metal hydrides such as sodium hydride and potassium hydride; metal alkoxides such as potassium tert-butoxide and magnesium ethoxide.

[0136] Examples of organic solvents used include aromatic hydrocarbons such as benzene and toluene; THF, 1, 4

— Ethers such as dioxane; Amides such as DMF;

[0137] The temperature for preparing the metal salt is usually 0 ° C to 120 ° C. The reaction temperature between the metal salt and the compound represented by formula (II) is usually from 0 ° C to 120 ° C, and the reaction time is usually from several minutes to several hours.

 [0138] Next, the obtained compound represented by the formula (VI) is decarboxylated in the presence of a catalytic amount of an acid in a solvent to obtain a compound represented by the formula (VII).

[0139] Examples of the acid used include sulfonic acids such as p-toluenesulfonic acid and methanesulfonic acid, organic acids such as acetic acid; inorganic acids such as sulfuric acid and hydrochloric acid; and the like.

[0140] Solvents used include aromatic hydrocarbons such as benzene and toluene; ethers such as THF and 1,4-dioxane; amides such as DMF; alcohols such as ethanol and methanol; these organic solvents And a mixed solvent of water and water;

 The reaction temperature is usually from 0 ° C to 120 ° C, and the reaction time is usually from several minutes to several hours.

Yes

 [0141] Next, the compound represented by the formula (VII) is used in an amount of 1 to 3 equivalents of the trialkylorthoester such as trimethylol onoletoacetate or triethyl orthoacetate with respect to the compound represented by the formula (VII); Alternatively, it is reacted with N, N-dialkylacetamide dialkylacetals such as N, N dimethylacetamide dimethylacetal to obtain a compound represented by the formula (VIII).

 [0142] This reaction can be carried out without solvent or in an organic solvent. Organic solvents to be used include aromatic hydrocarbons such as benzene and toluene; etheroles such as THF and 1,4 dioxane; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; Nitriles; and the like.

[0143] The reaction temperature is usually from 0 ° C to 120 ° C, and the reaction time is usually from several minutes to several hours. [0144] Next, the obtained compound represented by the formula (VIII) is reacted with 1 to 5 equivalents of hydroxyamine or the like to the compound represented by the formula (VIII) in the presence of a base. By the formula that is the target

A compound represented by (I Q6a) can be produced.

[0145] Examples of the base to be used include organic bases such as triethylamine; metal carbonates such as sodium carbonate; metal hydrogen carbonates such as sodium hydrogen carbonate; metal acetates such as sodium acetate;

 The amount of the base used is usually;! To 5 equivalents relative to the compound represented by the formula (VIII).

[0146] The reaction is preferably carried out in an organic solvent. Examples of the organic solvent to be used include the same organic solvents as those used for the reaction for obtaining the compound represented by the formula (VIII).

 The reaction temperature is usually from 0 ° C to 120 ° C, and the reaction time is usually from several minutes to several tens of hours.

In the compound of the present invention, in formula (I), a compound in which Q is a group represented by Q6 and G is a sulfur atom can be produced by a method represented by the following formula.

[0148] [Chemical 17]

 (Q6b) (I-Q6a)

[Wherein R1 to R3, R10, Rl 1 and p represent the same meaning as described above.]

 That is, first, an organic lithium such as n-butyllithium; an alkali metal alkoxide such as potassium t-butoxide; a base such as methylmagnesium bromide is added to the compound represented by the formula (Q6b) from −78 ° C. to +25 After acting in an organic solvent such as ethers such as jetyl ether and THF at ° C, this is reacted with a compound represented by formula (II) to give a formula (I Q6a) The target compound represented can be produced.

[0150] The compound represented by the formula (III) as the raw material compound is produced as shown in the following formula That's the power S.

[0151] [Chemical 18]

 (IX)

 (IV)

[Wherein R1 to R3, p and W represent the same meaning as described above, and R25 represents carbon number;! To 6 alkyl group; haloalkyl group having 1 to 6 carbon atoms; or 1 carbon number] ~ 3 alkyl group, carbon number;! ~ 6 haloalkyl group, carbon number 1-3 alkoxy group, carbon number 1-3 alkylthio group, carbon number;! ~ 3 alkylsulfonyl group, nitro group, cyan group And represents a phenyl group which may be substituted with a halogen atom or the like.)

 That is, a benzoate ester (IX) and a sulfoximine (X) are reacted according to a method described in the literature (for example, Synthesis, Vol. 7, p. 91 1-913, 2000 dried IJ, etc.). It is the power to produce benzoic acid ester (IV) by hydrolysis under general hydrolysis conditions.

 [0154] The starting benzoic acid ester (IX) is prepared by a known method (for example, JP-A 05-039259, JP-A 04-501726, JP-A 02-006426, JP-A 64-0527. No. 59, US 5092919, etc.] Med. Chem., 1972, No. 15, Vol. 6, p. 684)). In addition, this is a combination of general methods (eg, Organic Synthesis, colective volume 5, 412 shellfish, Organic synthesis, colective volume 5, page 142, Organic Synthesis, volume 79, page 43, etc.) Can also be synthesized.

 [0155] For example, benzoic acid (IX-1) can be synthesized as shown in the following formula.

[0156] [Chemical 19]

 (I Χ-Π) (I Χ-ΠΙ) (I X I)

[Wherein Rl, p and R25 have the same meaning as described above, provided that R1 is not substituted at the 4-position (para-position of the group represented by C (= 0) OR 25). W represents a methanesulfonyl group, a p-toluenesulfonyl group, a trifluoromethanesulfonyl group, a acetyl group, a benzoyl group, etc.)

 [0158] That is, a compound represented by the formula (IX-II) is nitrated to obtain a compound represented by the formula (IX-III), and the hydroxyl group is protected with a protecting group W ', whereby the formula (IX — The power of synthesizing the compound represented by 1).

 [0159] Examples of the nitrating agent used in the nitration reaction include nitric acid, concentrated nitric acid, fuming nitric acid, alkyl nitrate, nitronium salts such as NO + BF-, and the like.

 twenty four

 [0160] The nitration reaction is carried out without solvent or in a solvent depending on the type of nitrating agent used.

 For example, when fuming nitric acid is used, acetic acid or a mixed solvent of acetic acid and water is used as the solvent.

 [0161] The reaction temperature of the nitration reaction is usually 20 to + 40 ° C, and the reaction time is usually several hours to several tens of hours.

[0162] Next, the obtained compound represented by the formula (IX-III) is reacted with trifluoromethanesulfonic anhydride in the presence of a base such as triethylamine, so that W 'is trifluoromethane. A compound represented by the formula (IX-1) which is a sulfonyl group can be obtained.

[0163] Compound (X) can be synthesized by a known method (for example, the method described in Synthesis, 2000, Vol. 1, pages 1 to 64).

[0164] Examples of the salt of the compound (I) of the present invention include salts of alkali metals such as lithium, sodium and potassium.

Salts of alkaline earth metals such as calcium and magnesium; salts of transition metals such as iron and copper; salts of organic bases such as ammonia, triethylamine, tributylamine, pyridine and hydrazine;

These salts can be produced by a conventionally known method. [0165] In any reaction, after completion of the reaction, if purification of the product is necessary after the usual post-treatment operation, purification is performed by a known and conventional purification method such as distillation, recrystallization, or column chromatography. By doing so, it is possible to isolate Mejiro potato.

[0166] The compound (I) of the present invention may have optical isomers and may have a large number of tautomers. All such isomers are included within the scope of the present invention.

 The structure of the compound of the present invention is determined by the NMR spectrum, IR spectrum, MS spectrum, etc., with the force S.

 [0167] Representative examples of the compounds of the present invention that can be produced as described above are shown in combinations of Q shown in Tables 11 to 16 and Table 17; however, the compounds of the present invention are those compounds. It is not limited to.

 [0168] The abbreviations in the table have the following meanings.

 Me: Metinore, Et: Ethyl, Pr: Propyl, Pen: Pentinole, Bu: Butyl, Hex: Hexyl, Ph: Phenenole, n: Nonolemanole, i: Iso, t: Tertiary, c: Cyclo, Tosyl: p Tonolence Norejo: ^ Nore

 In addition, 6-CH2-5 shares the 6th and 5th positions, and forms a cyclopropane ring across the methylene group. 6—CH2CH2—4 shares the 6th and 4th positions and forms a cyclopentane ring across the ethylene group! /. Others are the same.

[0169] [Table 1]

1 Replacement example when Q is Q l

R5 G R7 R4

H 0 Me H

CF3 0 Et H

H 0 i-Pr H

Me 0 Me Me

Ph S Me H

PhCH2 0 OMe H

Tosyl 0 Me H

PhC = 0 0 Me H

PhCH2C = 0 0 Me H

Ph 0 0CF3 H

HC≡C 0 Me CF3

2-Pyridyl 0 Me cPr

EtOC (= 0) S02 Me NEt

MeS02 0 Me cHex

Et2N 0 Et CF3

2-Naphthyl 0 Me H

1-Naphthyl 0 Me H

CH2 = CHCH2 0 Me H

Ph s Et H

PhCH2 0 Et H

Tosyl 0 H H

Et2NC (= 0) 0 H H

PhCH2C = 0 0 Et H

Me2NS02 0 iPr H

2-Naphthyl so Et H

1-Naphthyl 0 CF3 H

CH2 = CHCH2 0 Et H

2-Naphthyl NMe Et H

1-Naphthyl s Et H

2-Naphthylmethyl 0 OMe H

3-Naphthylmethyl 0 Me H-Quinol inylraethyl 0 Me H-Pyridinylmethyl 0 Me H [0170] [Table 2] Table 1-2 Replacement example when Q is Q2

[0171] [Table 3]

Table 1-3 Replacement example when Q is Q3

[0172] [Table 4] Table 1-4 Replacement example when Q is Q4

Table 1-15 Replacement example when Q is Q5

Table 1-6 Replacement example when Q is Q6

[0175] [Table 7] Table 1-7 Replacement example when Q is Q7

 R5 R7 R4

H H H

 Me H Me

CF3 Me H

MeC≡C H Me

2-Pyridyl Et cPr

MeOC (= 0) iPr NH2

MeS02 n- Butyl NMe2

Et2N t-Butyl H

H cPrCH2 H

H MeO H

H EtO H

H EtO H

H EtO H

Ph Me H

Ph Me H

PhCH2 Me H

PhCH2 Me H

Tosyl Me H

Tosyl Me H

PhC = 0 Me H

PhC = 0 Me H e2NS02 Me H

PhCH2C = 0 Me H

Ph Me H

Ph Me H

2-Naphthyl Me H

Et2NC (= 0) Me H

1-Naphthyl Me H

1-Naphthyl Me H-Naphthylmethyl Me H- Naphthylmethyl Me H-Naphthylmethyl Me H-Naphthylmethyl Me H-Naphthylmethyl Me H- Naphthylmethyl Me H

CH2 = CHCH2 Me H

CH2 = CHCH2 Me H //: / O ε8ί890 / -00ί1 £ / -pss800iAV

Table 1-8 Replacement example when Q is Q8

R4 R6

H H

 Me Me iPr Et cPr iPr cPr n-Butyl cPr t-Butyl cPr cPr cPr Phenyl cPr 4-Me-Phenyl cPr 1-Naphtyl cPr 2-Maphtyl cPr N (CH3) 2

N (CH3) 2 H

 tBu H tBu H

Et H cHex H

NEt2 H

NMe2 H

NMe2 H

NMe2 Me

NMe2 Me

CH20Me Me Table 2 Compound examples in combination with the above substitution examples of Q1 to Q8

 (Rl) p R2 R3

 -Me Me Me

 -Me Me Et

 -Me Me n-Pr

 -Me Me i-Pr

 -Me Me c-Pr

 -Me Me n-Bu

 -Me Me CF3

 -Me CF3 CF3

 -Me CF3 Et

 -Me CF3 Ph

 -Me Me CF3CH2

 -Me Et CF3CH2

 -Me Et Et

 -Me Et n-Pr

 -Me Et i-Pr

 -Me Et c-Pr

 2-Me Et n-Bu

 2-Me Et t-Bu

 2-Me n-Pr n-Pr

 2-Me n-Pr i-Pr

 2-Me n-Pr c-Pr

 2-Me n-Pr n-Bu

 2-Me n-Pr t-Bu

 2-Me i-Pr c-Pr

 2-Me i-Pr n-Bu

 2-Me i-Pr t-Bu

 -Me Me Ph

 2-Me Me 2-Thienyl

2-Me Me 3-Thienyl

2-Me Me 2-Furyl

 -Me Me 3-Fury 1

 -Me Me 3-Isoxazolyl

2-Me Me 4-Isoxazolyl

2-Me Me 5-Isoxazoly 丄

 2-Me Me 2-Pyridyl

2-Me Me 3-Pyridyl -Me Me 4-Pyridyl t

^ s0781l

Table 2 continued

 (RD P R2 R3

 2-C1 Me 2-Pyridyl

2-CI Me 3-Pyridyl

2-C1 Me 4-Pyridyl

2-C1 Me Morphol ino

2- CI Me Piperidino

2-CI Me 4-Piperidyl

2-CI Me 4-Tetrahydropyranyl

2- CI-CH2CH2-

2-C1 -CH2CH2CH2-

2- CI -CH2CHMeCH2-

2-C1 -CH2CH2CH2CH2-

2- CI -CHMeCH2CH2CH2-

2- CI -CH2CHMeCH2CH2-

2-C1 -CH2CH2CH2CH2CH2-

2-C1 -CHMeCH2CH2CH2CH2-

2- CI -CHMeCH2CH2CH2CHMe-

2- CI -CH2CH2-0-CH2CH2-

2-C1-CH2C thigh (Me) CH2CH2-

2-C1 -CH2CH2 (C = 0) CH2CH2-

2- CI -CH2CH2C (OMe) 2CH2CH2-

2- CI -CH2CH (OMe) CH2CH2CH2-

2-CI -CH2C H2CH2CH2CH2CH2-

2-C1 Et Ph

 2-C1 Et 2-Thienyl

2- CI Et 3-Thienyl

2-C1 Et 2-Furyl

2-C1 Et 3-Furyl

2-C1 Et 3-Isoxazolyl

2-CI Et 4-Isoxazolyl

2-C1 Et 5-Isoxazolyl

2-CI Et 2-Pyridyl

2- CI Et 3-Pyridyl

2- CI Et 4-Pyridyl

2- CI Et Morphol ino

2- CI Et Piperidino

2-CI Et 4-Piperidyl

2- CI Et 4-Tetrahydropyranyl

2-C1 n-Pr Ph

 2-C1 n-Pr 2-Thienyl

2-C1 n-Pr 3-Thienyl

2-CI n-Pr 2-Furyl

2- CI n-Pr 3-Furyl Table 2 continued

 R2 R3

-C1 n-Pr 3-Isoxazolyl-C1 n-Pr 4-Isoxazolyl-C1 n-Pr 5-Isoxazolyl-C1 n-Pr 2-Pyridyl-C1 n-Pr 3-Pyridyl-C1 n-Pr 4-Pyridyl-C1 n-Pr Morpholino-C1 n-Pr Piperidino-C1 n-Pr 4-Piperidyl-C1 n-Pr 4-Tetrahydropyrany 1-MeO Me Me

-MeO Me Et

-MeO Me n-Pr-MeO Me i-Pr-MeO Me c-Pr-MeO Me n-Bu-MeO Et Et

-MeO Et n-Pr-MeO Et i-Pr-MeO Et c-Pr-MeO Et n-Bu-MeO Et t-Bu-MeO Me CF3

-MeO CF3 CF3

-MeO CF3 Et

-MeO CF3 Ph

-MeO Me CF3CH2-MeO Et CF3CH2-MeO n-Pr n-Pr-MeO n-Pr i-Pr-MeO n-Pr c-Pr-MeO n-Pr n-Bu-MeO n-Pr t-Bu-MeO i-Pr

-MeO i-Pr n-Bu-MeO i-Pr t-Bu-MeO Me Ph

-MeO Me 2-Thienyl-MeO Me 3-Thienyl-MeO Me 2-Furyl-MeO Me 3-Furyl-MeO Me 3-Isoxazolyl [0182] [Table 14]

Table 2 continued

[0183] [Table 15] Table 2 continued 6

Table 2 continued 9

 1

C8Z890 / Z.00ZdT / X3d gg [S D¾0812

C8Z890 / Z.00Zdf / X3d [] D¾¾09112

Table 2 continued 14

[0194] [Herbicide]

 The compound of the present invention or a salt thereof (hereinafter referred to as “the compound of the present invention”) is a weed such as fly, firefly, and oak that does not cause phytotoxicity when cultivating paddy rice (including widely rice). On the other hand, high herbicidal activity is exhibited by both soil treatment and foliage treatment.

[0195] The compounds of the present invention include those having bactericidal activity and insecticidal activity.

 The herbicide of the present invention contains one or more of the compounds of the present invention as active ingredients. When the herbicide of the present invention is actually applied, the compound of the present invention can be used in a pure form without adding other components, and a form that can be used by general agricultural chemicals for the purpose of use as an agricultural chemical. Use in the form of wettable powder, granule, powder, emulsion, water solvent, suspension, flowable, etc.

 [0196] When a solid agent is used as the additive and carrier, vegetable powder such as soybean powder and wheat flour, fine mineral powder such as diatomaceous earth, apatite, gypsum, talc, bentonite, neurophyllite, and clay, Organic and inorganic compounds such as sodium benzoate, urea and mirabilite are used.

 [0197] For liquid dosage forms, kerosene, xylene, solvent naphtha and other petroleum fractions, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol, acetone, trichloroethylene, Use methyl isobutyl ketone, mineral oil, plant oil, water, etc. as solvents.

 [0198] In order to obtain a uniform and stable form in these preparations, a surfactant may be added if necessary. The surfactant is not particularly limited. For example, alkyl phenyl ether added with polyoxyethylene, alkyl ether added with polyoxyethylene, higher fatty acid ester added with polyoxyethylene, sorbitan added with polyoxyethylene. Higher fatty acid esters, nonionic surfactants such as tristyryl phenyl ether added with polyoxyethylene, sulfates of alkyl phenyl ethers added with polyoxyethylene, alkyl naphthalene sulfonates, polycarboxylates , Lignin sulfonate, formaldehyde condensate of alkyl naphthalene sulfonate, isoprene-maleic anhydride copolymer, and the like.

[0199] The active ingredient concentration in the herbicide of the present invention can be varied depending on the form of the preparation described above. Forces that change, for example, 5 to 90% by weight (hereinafter simply referred to as%) in wettable powders, preferably 10 to 85%: 3 to 70% in emulsions, preferably Is 5 to 60%: in granules, a concentration of 0.01 to 50%, preferably 0.05 to 40% is used.

 [0200] The wettable powder and emulsion thus obtained are diluted with water to a predetermined concentration to form a suspension or emulsion, and the granules are directly applied to the soil before or after germination of weeds. It is mixed. In practice, when applying the herbicide of the present invention, an appropriate amount of 0. lg or more of active ingredient is applied per hectare.

 [0201] The herbicide of the present invention can also be used by mixing with known fungicides, insecticides, acaricides, herbicides, plant growth regulators, fertilizers, safeners and the like. In particular, the amount of drug used can be reduced by using it in combination with herbicides. Moreover, not only can labor be saved, but a higher effect can be expected due to the synergistic action of the mixed drugs. In that case, a combination with a plurality of known herbicides is also possible.

[0202] Examples of drugs suitable for use in combination with the herbicide of the present invention include: anilide herbicides such as diflufenican, picolinaphene, propanil; and croloacetanilide herbicides such as alachlor and pretilachlor; 2, 4 — Aryloxyalkanoic acid herbicides such as D, 2, 4— DB and MCPB; Aryloxyphenoxyalkanoic acids such as diclohopumethyl, phenoxapropetyl, and cihalohop butyl Herbicides: Cyclohexanedione herbicides such as cetoxydim and tolalkoxydim, carboxylic acid herbicides such as dicampa and picloram; imidazolinone herbicides such as imazaquin and imazetapir; , Carbamate herbicides such as chlorprofam and fenmedifam; thiobencalp, EPTC, etc. Thiocarbamate herbicides; dinitroarine herbicides such as trifluralin and pendimethalin; diphenyl ether herbicides such as acifluorfen and fomesafen; sulfone lurea herbicides such as bensulfuron-methyl and nicosulfuron; Pyrimidinyl carboxy-based herbicides such as pyrithiobac, bispyribac, and pyriminobac; triazinone herbicides such as metribudine and metamitron; triazine-based herbicides such as atrazine, cyanazine, cimethrin, and dimetamethrin; uracil herbicides such as bromacil and lenacyl; Triazolopyrimidine herbicides such as flumelamum and penox slam; nitrile herbicides such as bromoxyshell and diclobenil; Acidic herbicides; bibilidilium herbicides such as paraquat and diquat; cyclic imide herbicides such as flumioxazin, funole microlac pentyl and fluthiaset methyl; benzoes such as benzoylpropetyl and frumpropethyl Illaminopropionic acid herbicide;

 [0203] MSMA, Ashram, Chloridazone, Norflurazon, Flutamon, Fluorochloridone, Flucarbazone Na salt, Propoxycarbazone Na salt, Ami force rubazone, Isoxaben, Funolepoxam, Kink mouth rack, Kinmerac, Diflufenzopyr Na salt , Oxaziazone, Oxazianoreginore, Anilofos, Piperofos, Daimlone, Bentazone, Benfresate, Etofumesate, Difenzocote, Naproanilide, Triazofuenamide, Cromazone, Sulcotrione, Mesotrione, Topramison, Tefriltrione, Tempo Trione, pyrasul photomonole, isoxaflutol, isoxachlortol, dithiopyr, thiazopyr, amitrol, birazoxifene, pyrazolate, benzobicyclon, pyridate, pyrida Fuol, azaphenidine, carfentrazone-ethyl, sulfentrazone, pentoxazone, pyrafnole phenethyl, fluazolate, flufenpyruethyl, butaphenacyl, pyrachronyl, ben force rubazone, symmetrine, oxadichrome mephone, dimethenamide, mefenacet And other herbicides such as phentolazamide, indanophane, caffenstrol, piributicalp, pyrimisulfan, pinoxaden, pyroxasulfone, quinoclamine, and the like. Benoxacol is a safener suitable for use in combination with the herbicide of the present invention. , Croquintoset-mexil, ciomethrinyl, cyprosulfamide, dichlormide, dicyclonone, dietolate, fenchlorazole-ethyl, fenchlorim, full Zonore, old Sofuenimu, furilazole, isoxadifen over E chill, main phen pin Rougier chill, Mefue sulfonates, naphthalate Rick anhydride, Okisabetoriniru, daimuron and the like. In addition, it is possible to add additives such as vegetable oils and oil concentrates to the combined composition.

 Example

[0204] Next, the present invention will be described in more detail with reference to Examples and Reference Examples, but the present invention is not limited to the following Examples. [0205] {Aza [2 Chloro-3— [(5 Hydroxy 'Metino Levillazonole 4

 6] -Nitrophenyl] methylene} thianon (I 1) production [0206]

[0207] 3- [Aza (Oxothiauridene) methyl] -2 Chloro-4,12-trobenzoic acid (a) 9 · —Carbonyldiimidazole 7. Og was added at room temperature, and the mixture was stirred for 1 hour at room temperature. Thereto were added 3.2 g of N-methylpyrazolone and 3.3 g of triethylamine, and the whole was heated to reflux for 1.5 hours. The reaction solution was cooled and the solvent was concentrated. To the obtained residue, acetonitrile 180 ml, molecular sieve 3A 9 • 0 g, acetone cyanohydrin 0.7 g, and triethinoreamine 8.2 g were calorie-free, and the whole volume was stirred at room temperature for 3 days. Insoluble matters were filtered from the reaction mixture, and the filtrate was concentrated. The residue was dissolved in 600 ml of chloroform, and this solution was washed with 300 ml of 1N hydrochloric acid and then with water (500 ml), and then the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to obtain 13. lg of a crude product. Crystallize by adding 30 ml of methanol, and after filtration, wash the crystals with 20 ml of methanol. 1- {aza [2-chloro-3- [(5-hydroxy 1-methylbilazole-4-ynole) carbonyl] -6 6.4 g of pale yellow crystals of —nitrophenyl] methylene} thian-1-one (1-1) were obtained. Yield 57%, melting point: 200-203 ° C.

 The compound represented by the formula (a) as a raw material was synthesized according to the method described in the above-mentioned WO 04/052849 pamphlet.

[0208] (Example 1 2) 1 {Aza [2-Chloro-3- [(5-Hydroxy-1-methylbilazole- 4-Inole) carbonyl]-6-Nitrophenyl] methylene} thiane 1 —Manufacture of on (1—1) [0209] [Chemical 21]

[0210] 2 Chloro-4 12-tallow 3— (1-oxotetrahydrothiopyran-1 iridenamino) Benzoic acid (a) 9. Og in chloroform form 320 ml solution, oxalyl chloride 4 · lg, and touch As a medium, 0.1 ml of N, N dimethylformamide was added, and the whole was heated to reflux for 1 hour. The reaction mixture was cooled with ice water, 3.4 g of N-methylpyrazolone and 4. lg of triethylamine were added, and the whole was stirred at room temperature for 3 hours. The solvent was distilled off from the resulting reaction mixture.

 [0211] 180 ml of acetonitrile and molecular sieve 3A 9. Og, 0.7 g of acetone cyanohydrin, and 8.2 g of triethylamine were added to the residue, and the mixture was stirred at room temperature for 1 day. Insoluble matters were filtered from the reaction mixture, and the filtrate was concentrated. The residue was dissolved in 600 ml of black mouth form, washed with 300 ml of 1N hydrochloric acid and then washed with water (500 ml), dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product. Crystallize by adding 30 ml of methanol, and after filtration, wash with 20 ml of methanol. 1 {aza [2-chloro-3- [(5-hydroxy 1-methylbiazole- 4-inore) carbonino]]-6 nitrophenyl] methylene } 7.0 g of yellow crystals of thiane 1-one (1-1) were obtained. Yield 63%, melting point: 193-194 ° C.

 [0212] (Example 2) 1— {Aza [2 Black Mouth 3— [(1-Methyl 5- (Phenylmethoxy) pyrazole Noreno 4-Inole) carbonyl] 6 Nitrophenyl] methylene} thian 1-one ( I—2)

[0213] [Chemical 22]

[0214] 1 {Aza [2 Chloro-3 — [(5 Hydroxy 1-methylbilazole-4-Inole) Force] Bonyl] —6 Nitrophenyl] methylene} thian 1-one (1-1) 0-3 g N , N dimethylformamide was dissolved in 4 ml and potassium carbonate 0.12 g was added. Thereto was further added 0.12 g of benzyl bromide, and the whole was stirred at room temperature for 24 hours.

[0215] Water and ethyl acetate were added to the reaction solution, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (ethyl acetate: _n- hexane = 3/7 (volume ratio)), and 1 {aza [2 chloro-3- [(1-methyl-5- (phenylmethoxy) pyrazole- 4- (inole) carbonyl] -6-nitrophenyl] methylene} thian-1-one (1-2) was obtained as a pale yellow amorphous compound (0.31 g). (Yield 84%)

 [0216] Production examples of the compounds of the present invention, including the above examples, are shown in Tables 3-1 to 3-9. Abbreviations have the same meaning as in Table 1.

 In the table, Al and A2 represent the groups shown below.

[0217] [Chemical 23]

[0218] [Chemical 24]

 ().

姗 HS ^^ Id ^ o¾ 31o-1 ¾02

£ 8S9 // 0 / -0S1: 2 OZ /-£ / z-ss800 OzAV

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Compounds in which Q is substituted with Q3

3]

Table 3-4 Compounds where Q is replaced with Q4

Four] Table 3-5 Compounds with Q substituted by Q5

[0228] [Table 35] Table 3-6 Compounds in which Q is substituted with Q6

Three

 —

[0229] [Table 36] Table 3-7 Compounds with Q substituted by Q7

 Compound R4 R5 7 (Rl) p R2 R3 number

 Q7-1 H C (= 0) 0-i-Pr Me 2- CI -CH2CH2CH2CH2CH2- amorphous

Q7-2 H Benzyl Me 2- CI -CH2CH2CH2CH2CH2- amorphous

Q7-3 H 2-Naphtylmethyl Me 2-CI -CH2CH2CH2CH2CH2- amorphous

 4- Me-

Q7-4 H Me 2-C1 -CH2CH2CH2CH2CH2- amorphous benzoylmethyl [0230] [Table 37]

Table 3—Compounded compounds

[0231] [Table 38]

Table 3-9 Compounds with sulfoxymino group bonded to the 2-position

[0232] — NMR data (internal standard TMS) is shown in Table 4 below.

 The unit is δ ppm. The numbers in parentheses indicate the proton ratio, and the symbols are s: singlet, d: doublet, t: triplet, q: quartet, m: multiplet, br: broad, brs: blow Compound numbers are shown in Table 3-1 to Table It corresponds to 3-8.

[0233] [Table 39] Table 4

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] Table 4 (continued)

] Table 4 (continued)

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£ 8 890 Female dfA! Od 8 ε ^ εο / 800 ΟΛ \ Table 4 (continued)

 [0243] [Table 49]

 Table 3 (Kneaded)

 [0244] Next, some preparation examples relating to the herbicide of the present invention will be shown. However, the active ingredient compounds, additives and addition ratios can be varied within a wide range without being limited only to this example. The part in a formulation example shows a weight part.

[0245] Formulation Example 1 wettable powder

 20 parts of the present compound

 20 parts of white carbon

 52 diatomaceous earth

 Alkyl sulfate soda 8 parts

 The above is uniformly mixed and finely pulverized to obtain a wettable powder of 20% active ingredient.

[0246] Formulation Example 2 Emulsion

20 parts of the present compound Xylene 55 parts

 Dimethylformamide 15 parts

 10 parts of polyoxyethylene phenyl ether

 The above is mixed and dissolved to obtain an emulsion of 20% active ingredient.

[0247] Formulation Example 3 Granules

 Compound of the present invention 5 parts

 Tanorek 40 copies

 38 parts of clay

 10 parts of bentonite

 Alkyl sulfate soda 7 parts

 After the above is uniformly mixed and finely pulverized, the mixture is granulated into granules having a diameter of 0.5 to 1.0 mm to obtain granules having an active ingredient content of 5%.

[0248] Next, test examples relating to the effects of the herbicide of the present invention are shown.

 Test example 1

After filling paddy soil with water added to a resin pot with an area of 100 cm ² and depth of 10 cm, sowing seeds of nobier and firefly, 2.5 transplanting rice at the leaf stage to make it submerged It was. Growing in a greenhouse and treating the pot with a chemical solution prepared so that the amount of the drug component is 63 g per lha at the time when the leaves of Nobies reached 1.5 leaves, and after 3 weeks, herbicide effect and rice Judgment of phytotoxicity was made. The results are shown in Table 5. The compound numbers correspond to Table 3-1 to Table 3-9

Yes

 In Comparative Examples 1 to 3, the following compounds (compounds described in WO04 / 052849 pamphlet) were used.

[0249] [Chemical 25]

[0250] The herbicidal effect was investigated according to the following survey criteria and expressed in terms of herbicidal index. [0251] Survey criteria

 Slaughter rate

 0%

 20-29%

 40-49%

 60-69%

 80-89%

 100%

 The numbers 1, 3, 5, 7, and 9 indicate 0 and 2, 2 and 4, 4 and 6, 6 and 8, and 8 and 10, respectively.

[0252] [Equation 1]

 Herbicide rate (%) =

 (Untreated terrestrial fresh grass a-treated terrestrial fresh grass weight) / (Untreated territory t part cattle grass Φ> X 1 0 0

[0253] [Table 50]

Table 5

5 Table (continued)

Table 5 (continued)

Table 5 (continued)

 Compound dose

 Rice Hee Hotanorei number g (ai / ha)

 Q1-92 63 0 7 8

01-95 63 0 10 9

Q1-96 63 0 10 8

Q1-97 63 0 10 8 [0257] [Table 54]

Table 5 (continued)

[0258] [Table 55]

Table 5 (continued)

 [0259] [Table 56]

Table 5 (continued)

 [0260] [Table 57]

Table 5 (continued)

[0261] [Table 58] Table 5 (continued)

Table 5 (continued)

 Compound dose

 Rice hye firefly number g (ai / ha)

 Comparative Example 1 63 7 9 8 Comparative Example 2 63 0 0 4 Comparative Example 3 63 0 3 5

Claims

The scope of the claims

 [1] Formula [I]

 [Chemical 26]

[Wherein R 1 represents a halogen atom, a hydroxyl group, a mercapto group, an unsubstituted or substituted amino group, a nitro group, or an organic group.

 p represents an integer of 0 to 3. When p is 2 or more, plural R1s may be the same or different.

 R2 and R3 are each independently an unsubstituted or substituted alkyl group, an unsubstituted or substituted cycloalkyl group, an unsubstituted or substituted alkenyl group, an unsubstituted or substituted alkynyl group. Represents an unsubstituted or substituted aryl group or an unsubstituted or substituted heterocyclic group.

 R2 and R3 are joined together to form a 3- to 8-membered unsubstituted or substituted heterocycle which may contain 1 to 4 nitrogen, oxygen or sulfur atoms. May be.

 Q represents a kind of group selected from groups represented by the following formulas Q1 to Q8.

[Chemical 27]

 Q5 Q6 Q7 Q8

(In the formula, * represents a binding site.

 G represents an oxygen atom, a sulfur atom which may be oxidized, or a nitrogen atom which may have a substituent.

 R4 represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted cycloalkyl group, or an unsubstituted or substituted amino group.

R5 represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkenyl group, an unsubstituted or substituted alkynyl group, an unsubstituted or substituted aryl group, unsubstituted or A substituted heteroaryl group, an unsubstituted or substituted alkylcarbonyl group, an unsubstituted or substituted alkoxycarbonyl group, an unsubstituted or substituted benzoyl group, an unsubstituted or substituted aminocarbonyl group And represents an unsubstituted or substituted alkylsulfonyl group, an unsubstituted or substituted arylsulfonyl group, or an unsubstituted or substituted aminosulfonyl group.

 R6 represents a cyano group, a acetyl group, a group represented by the formula: C = NR7, or an unsubstituted or substituted tetrazolyl group.

R7 is a hydrogen atom, an unsubstituted or substituted alkyl group, unsubstituted or substituted. An alkoxy group having a substituent is represented.

 R8 and R9 each independently represent a hydrogen atom or an unsubstituted or substituted alkyl group.

 R10 and Rl1 each independently represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted cycloalkyl group.

 X represents a group represented by the formula: C (R12) (Rl 3) or a group represented by the formula NR12.

 R12 and Rl3 each independently represents a hydrogen atom or an unsubstituted or substituted alkyl group.

 Y represents an oxo group, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted alkoxycarbonyl group.

 m represents 0 /! or any integer.

 When m is 2 or more, a plurality of Y may be the same or different from each other. Y may be bonded to each other to form an unsubstituted or substituted alkylene group. Alternatively, Y and X R12 may combine to form an unsubstituted or substituted alkylene group! /. ] 4-Nitrobenzoyl derivative represented by these, or its salt.

 [2] In the formula [I], R1 is a halogen atom, an unsubstituted or substituted alkyl group, or a formula: N = S (= O) R2R3 (R2 and R3 have the same meaning as described above). The 4-nitrobenzoyl derivative or a salt thereof according to claim 1, which is a compound.

 [3] One of the 4 nitrobenzoyl derivatives or salts thereof according to claim 1 or 2, or

 A herbicide for paddy rice containing two or more active ingredients.