JP2005314407A - New haloalkylsulfonanilide derivative, herbicide, method for using the same and intermediate therefor - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a herbicide excellently safe for humans and animals, having high selectivity for crops, exhibiting high herbicidal effects with a low dose and having wide applicability, persistence of the effects and excellent selectivity between crops and weeds and especially excellent performances as a paddy herbicide. <P>SOLUTION: A haloalkylsulfonanilide derivative is represented by general formula (I) [wherein, R<SP>1</SP>denotes a halo(1-6C)alkyl; R<SP>2</SP>and R<SP>5</SP>denote each an H, a (1-6C)alkyl, a (substituted) phenyl(1-6C)alkyl or the like; R<SP>3</SP>, R<SP>4</SP>, R<SP>6</SP>and R<SP>7</SP>denote each an H, a (1-6C)alkyl, a (3-6C)cycloalkyl, a halogen, a CN or the like; R<SP>3</SP>and R<SP>4</SP>may mutually be bound to form a 3- to a 7-membered ring; R<SP>6</SP>and R<SP>7</SP>may mutually be bound to form a 3- to a 7-membered ring; A denotes O or S; G denotes O, S or a CR<SP>8</SP>, R<SP>9</SP>äwherein, R<SP>8</SP>and R<SP>9</SP>denote each H, a (1-6C)alkyl or the like}; Q denotes a (1-6C)alkyl, a (substituted) (3-6C)cycloalkyl or the like; a and b denotes each 0 or 1; and X denotes H, a halogen, a (1-6C)alkyl, a (substituted) phenyl, a (substituted) heterocyclic ring or the like]. The herbicide comprises the haloalkylsulfonanilide derivative or its salts as an active ingredient. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to a novel haloalkylsulfonanilide derivative or a salt thereof, a herbicide containing the compound as an active ingredient, and a method for using the herbicide. The invention further relates to intermediates for producing the compounds.

  Conventionally, diphenyl ether derivatives having a perfluoroalkylsulfonylamino group as a substituent have been known to be useful as herbicides or anti-inflammatory agents, but there is no description or suggestion of skeletons other than diphenyl ether (for example, patents) Reference 1). Perfluoroalkylsulfonanilide derivatives having a phenoxy group, phenylthio group, phenylsulfonyl group, etc. as substituents are used as herbicides or anti-inflammatory agents, and urea derivatives having a trifluoromethanesulfonylamino group as substituents are used as herbicides, trifluoromethanesulfonyl. Pyrazine derivatives having amino groups are known as herbicides, but the haloalkylsulfonanilide derivatives of the present invention are not described or suggested, and between rice and paddy weeds as the haloalkylsulfonanilide derivatives of the present invention have. There is no description about selective herbicidal properties (see, for example, Patent Documents 2, 3, and 4). A heterocyclic derivative having a trifluoromethanesulfonanilide structure is known as a herbicide, but it is a skeleton in which trifluoromethanesulfonanilide and a heterocyclic ring are directly bonded, and a spacer such as an alkylene group like the haloalkylsulfoneanilide derivative of the present invention. There is no description or suggestion of a skeletal compound bonded via a ring (see, for example, Patent Document 5). A sulfonanilide derivative having a 2-pyrimidinyloxy group at the 4-position and a herbicide containing the compound as an active ingredient are known, and rice has no phytotoxicity and is applicable to paddy fields. The skeleton is different from the haloalkylsulfonanilide derivative of the invention, and there is no particular description or suggestion of other skeletons (see, for example, Patent Documents 6 and 7). A compound having a skeleton in which a haloalkylsulfonanilide and a heterocycle are bonded to a nitrogen atom in the heterocycle via a spacer such as an alkylene group is known as a herbicide. However, a haloalkylsulfonanilide such as the haloalkylsulfonanilide derivative of the present invention is known as a herbicide. There is no description or suggestion of a skeleton compound bonded to a nitrogen atom that does not constitute a ring via an alkylene group or the like (see, for example, Patent Document 8).

US Pat. No. 3,906,024 German Patent Application No. 2118190 JP 60-87254 A U.S. Pat. No. 4,345,076 European Patent Application No. 11893 JP-A-8-193011 JP-A-8-291146 International Publication No. 04/11429 Pamphlet

  As described above, it is known that certain haloalkylsulfonamide derivatives are useful as herbicides, but their herbicidal effect, wide applicability to many weed species including difficult-to-control weeds, sustained effect, Properties such as excellent selectivity between crops and weeds are not sufficient, and the creation of herbicides with more excellent properties has been demanded.

  As a result of intensive studies on the synthesis of a derivative having a sulfonanilide structure and its physiological activity in order to develop a novel herbicide, the present inventors have made a novel haloalkylsulfone represented by the general formula (I) of the present invention. Anilide derivative is a novel compound not described in the literature, and has a significant herbicidal effect compared to the compounds disclosed in the prior art, wide applicability to many weed species including difficult-to-control weeds, long-lasting effect, excellent crops- It has characteristics such as selectivity between weeds, and has been found to be useful as a herbicide, particularly as a herbicide for paddy fields, and has completed the present invention.

｛式中、Ｒ¹はハロ（C₁-C₆）アルキル基を示す。Ｒ² は水素原子、（C₁-C₆）アルキル基、（C₁-C₆）アルコキシ（C₁-C₆）アルキル基、フェニル（C₁-C₆）アルキル基、同一又は異なっても良く、Ｙ（Ｙは後記に示す。）から選択される１〜５個の置換基を環上に有する置換フェニル（C₁-C₆）アルキル基、（C₁-C₆）アルキルカルボニル基、ハロ（C₁-C₆）アルキルカルボニル基、（C₂-C₆）アルケニルカルボニル基、フェニルカルボニル基、同一又は異なっても良く、Ｙ（Ｙは後記に示す。）から選択される１〜５個の置換基を有する置換フェニルカルボニル基、複素環カルボニル基（複素環はピリジン環、ピリミジン環、ピラジン環、トリアジン環、オキサチイン環、ジヒドロオキサチイン環、フラン環、テトラヒドロフラン環、チオフェン環、テトラヒドロチオフェン環、テトラヒドロピラン環、テトラヒドロチオピラン環、オキサゾール環、オキサゾリン環、イソキサゾール環、イソキサゾリン環、オキサジアゾール環、チアゾール環、チアゾリン環、イソチアゾール環、チアジアゾール環、イミダゾール環、イミダゾリン環、トリアゾール環、トリアゾリン環、ピラゾール環、ピラゾリン環、ピロール環又はピロリジン環を示す。）、同一又は異なっても良く、Ｙ（Ｙは後記に示す。）から選択される１〜５個の置換基を有する置換複素環カルボニル基（複素環は前記に同じ。）、（C₁-C₆）アルコキシカルボニル基、ハロ（C₁-C₆）アルコキシカルボニル基、フェノキシカルボニル基、同一又は異なっても良く、Ｙ（Ｙは後記に示す。）から選択される１〜５個の置換基を有する置換フェノキシカルボニル基、（C₁-C₆）アルキルチオカルボニル基、（C₁-C₆）アルキルスルホニル基、ハロ（C₁-C₆）アルキルスルホニル基、フェニルスルホニル基、同一又は異なっても良く、Ｙ（Ｙは後記に示す。）から選択される１〜５個の置換基を有する置換フェニルスルホニル基、（C₁-C₆）アルキルチオ（C₁-C₆）アルキル基、ハロ（C₁-C₆）アルキルチオ（C₁-C₆）アルキル基、フェニルチオ（C₁-C₆）アルキル基、同一又は異なっても良く、Ｙ（Ｙは後記に示す。）から選択される１〜５個の置換基を環上に有する置換フェニルチオ（C₁-C₆）アルキル基、（C₁-C₆）アルキルスルフィニル（C₁-C₆）アルキル基、ハロ（C₁-C₆）アルキルスルフィニル（C₁-C₆）アルキル基、フェニルスルフィニル（C₁-C₆）アルキル基、同一又は異なっても良く、Ｙ（Ｙは後記に示す。）から選択される１〜５個の置換基を環上に有する置換フェニルスルフィニル（C₁-C₆）アルキル基、（C₁-C₆）アルキルスルホニル（C₁-C₆）アルキル基、ハロ（C₁-C₆）アルキルスルホニル（C₁-C₆）アルキル基、フェニルスルホニル（C₁-C₆）アルキル基又は同一若しくは異なっても良く、Ｙ（Ｙは後記に示す。）から選択される１〜５個の置換基を環上に有する置換フェニルスルホニル（C₁-C₆）アルキル基を示す。 That is, the present invention relates to the general formula (I)

{Wherein R ¹ represents a halo (C ₁ -C ₆ ) alkyl group. R ² represents a hydrogen atom, a (C ₁ -C ₆ ) alkyl group, a (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group, a phenyl (C ₁ -C ₆ ) alkyl group, or the same or different Well, a substituted phenyl (C ₁ -C ₆ ) alkyl group having 1 to 5 substituents selected from Y (Y is shown below) on the ring, (C ₁ -C ₆ ) alkylcarbonyl group, ₁ to 5 selected from halo (C ₁ -C ₆ ) alkylcarbonyl group, (C ₂ -C ₆ ) alkenylcarbonyl group, phenylcarbonyl group, which may be the same or different, and Y (Y is shown below) A substituted phenylcarbonyl group having a number of substituents, a heterocyclic carbonyl group (the heterocyclic ring is a pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, oxathiin ring, dihydrooxathiin ring, furan ring, tetrahydrofuran ring, thiophene ring, tetrahydrothiophene Ring, tetra Dropyran ring, tetrahydrothiopyran ring, oxazole ring, oxazoline ring, isoxazole ring, isoxazoline ring, oxadiazole ring, thiazole ring, thiazoline ring, isothiazole ring, thiadiazole ring, imidazole ring, imidazoline ring, triazole ring, triazoline ring, A pyrazole ring, a pyrazoline ring, a pyrrole ring or a pyrrolidine ring.), Which may be the same or different, and a substituted heterocyclic carbonyl group having 1 to 5 substituents selected from Y (Y is shown below) (The heterocycle is the same as above.), (C ₁ -C ₆ ) alkoxycarbonyl group, halo (C ₁ -C ₆ ) alkoxycarbonyl group, phenoxycarbonyl group, the same or different, Y (Y is described later) A substituted phenoxycarbonyl group having 1 to 5 substituents selected from: (C ₁ -C ₆ ) alkylthiocarbonyl group, (C ₁ -C ₆ ) alkylsulfonyl group, halo (C ₁ -C ₆ ) alkylsulfonyl group, phenylsulfonyl group may be the same or different, and Y (Y is shown below). ) Substituted phenylsulfonyl group having 1 to 5 substituents selected from: (C ₁ -C ₆ ) alkylthio (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkylthio (C _1- C ₆ ) alkyl group, phenylthio (C ₁ -C ₆ ) alkyl group, which may be the same or different, and a substituent having 1 to 5 substituents selected from Y (Y is shown below) on the ring Phenylthio (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkylsulfinyl (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkylsulfinyl (C ₁ -C ₆ ) alkyl group, phenylsulfinyl (C ₁ -C ₆₎ alkyl groups, the same or different and, Y (Y It is shown in the following. 1-5 substituted phenylsulfanyl having a substituent on the ring nyl (C ₁ -C ₆₎ alkyl group selected from), (C ₁ -C ₆₎ alkylsulfonyl (C ₁ -C ₆₎ alkyl group, halo (C ₁ -C ₆ ) alkylsulfonyl (C ₁ -C ₆ ) alkyl group, phenylsulfonyl (C ₁ -C ₆ ) alkyl group, which may be the same or different and selected from Y (Y is shown below). A substituted phenylsulfonyl (C ₁ -C ₆ ) alkyl group having 1 to 5 substituents on the ring.

R ³ and R ⁴ may be the same or different, and are a hydrogen atom, a (C ₁ -C ₆ ) alkyl group, a (C ₃ -C ₆ ) cycloalkyl group, a (C ₁ -C ₆ ) alkoxy group, a halogen atom or A cyano group is shown. R ³ and R ⁴ can be bonded to each other to form a ^3- to 7-membered ring.
R ⁵ is a hydrogen atom, (C ₁ -C ₆ ) alkyl group, (C ₃ -C ₆ ) cycloalkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkyl group, phenyl ( C ₁ -C ₆ ) alkyl group, which may be the same or different, and substituted phenyl (C ₁ -C ₆ ) having 1 to 5 substituents selected from Y (Y is shown below) on the ring An alkyl group, a phenyl group, which may be the same or different, a substituted phenyl group having 1 to 5 substituents selected from Y (Y will be described later), and a heterocyclic group (the heterocyclic ring is the same as above. ), May be the same or different, and is a substituted heterocyclic group having one or more substituents selected from Y (Y is shown below) (the heterocyclic ring is the same as above), (C ₁ -C ₆ ) alkoxycarbonyl (C ₁ -C ₆₎ alkyl group, phenoxycarbonyl (C ₁ -C ₆₎ alkyl groups, the same or different and, Y (Y is described below Shown.) Substituted phenoxycarbonyl (C ₁ -C ₆₎ alkyl group having from 1 to 5 substituents selected on the ring from, mono (C ₁ -C ₆₎ alkylaminocarbonyl (C ₁ -C ₆₎ alkyl group, the same or different and may di (C ₁ -C ₆₎ alkylaminocarbonyl (C ₁ -C ₆₎ alkyl group, phenyl aminocarbonyl (C ₁ -C ₆₎ alkyl groups, the same or different and, A substituted phenylaminocarbonyl (C ₁ -C ₆ ) alkyl group having 1 to 5 substituents selected from Y (Y is shown below) on the ring, phenyl (C ₁ -C ₆ ) alkylaminocarbonyl A substituted phenyl (C ₁ -C ₆₎ having 1 to 5 substituents selected from (C ₁ -C ₆ ) alkyl group or the same or different, Y (Y is shown below) on the ring ) Represents an alkylaminocarbonyl (C ₁ -C ₆ ) alkyl group.
R ⁶ and R ⁷ may be the same or different and are a hydrogen atom, a (C ₁ -C ₆ ) alkyl group, a (C ₃ -C ₆ ) cycloalkyl group, a (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆₎ alkoxycarbonyl group, a halogen atom or a cyano group. R ⁶ and R ⁷ can be bonded to each other to form a 3- to 7-membered ring.

A represents an oxygen atom or a sulfur atom.
G is an oxygen atom, a sulfur atom, —C (R ⁸ ) (R ⁹ ) — (wherein R ⁸ and R ⁹ may be the same or different, a hydrogen atom, a (C ₁ -C ₆ ) alkyl group, ( C ₃ -C ₆ ) cycloalkyl group, (C ₁ -C ₆ ) alkoxy group, halogen atom or cyano group, and R ⁸ and R ⁹ may be bonded to each other to form a 3- to 7-membered ring. And can be combined with R ⁶ or R ⁷ to form a 4- to 7-membered ring.), A carbonyl group, a group represented by —C (═CH ₂ ) —, or —C (═NOR ^10. )-(Wherein R ¹⁰ may be a hydrogen atom, a (C ₁ -C ₆ ) alkyl group, a phenyl (C ₁ -C ₆ ) alkyl group, or the same or different, and Y (Y is shown below). Represents a substituted phenyl (C ₁ -C ₆ ) alkyl group having 1 to 5 selected substituents on the ring.).
Q may be a (C ₁ -C ₆ ) alkyl group, a halo (C ₁ -C ₆ ) alkyl group, a (C ₃ -C ₆ ) cycloalkyl group, and may be the same or different, and Y (Y is shown below). (C ₃ -C ₆ ) cycloalkyl group, cyano group, amino group, (C ₁ -C ₆ ) alkoxycarbonyl group, (C ₁ -C ₆ ) alkoxycarbonylamino group having one or more substituents selected from The phenylcarbonylamino group may be the same or different, and the substituted phenylcarbonylamino group having 1 to 5 substituents selected from Y (Y will be described later), the phenyl group may be the same or different. , Y (Y is shown below), a substituted phenyl group having 1 to 5 substituents, a heterocyclic group (the heterocyclic ring is the same as above), or the same or different, Y (Y Is a substituent having one or more substituents selected from: Heterocyclic group (heterocyclic ring are the same. Above) shows a.
a and b may be the same or different and represent 0 or 1;

X may be the same or different and is a hydrogen atom, halogen atom, (C ₁ -C ₆ ) alkyl group, (C ₂ -C ₆ ) alkenyl group, (C ₂ -C ₆ ) alkynyl group, cyclo (C _3- C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, cyclohalo (C ₃ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, ( C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylthio (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkylthio (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkylsulfinyl groups, halo (C ₁ -C ₆₎ alkylsulfinyl group, (C ₁ -C ₆₎ alkylsulfonyl groups, halo (C ₁ -C ₆₎ alkylsulfonyl group, a phenyl group, the same or different In addition, a substituted phenyl group having 1 to 5 substituents selected from Y (Y is shown below), a phenoxy group, may be the same or different, and is selected from Y (Y is shown below). A substituted phenoxy group having 1 to 5 substituents, a phenylthio group, which may be the same or different, and a substituted phenylthio group having 1 to 5 substituents selected from Y (Y is shown below), A phenylsulfinyl group, which may be the same or different, a substituted phenylsulfinyl group having 1 to 5 substituents selected from Y (Y will be described later), a phenylsulfonyl group, which may be the same or different; A substituted phenylsulfonyl group having 1 to 5 substituents selected from (Y is shown below), (C ₁ -C ₆ ) alkylcarbonyl group, halo (C ₁ -C ₆ ) alkylcarbonyl group, phenyl Cal Group, which may be identical or different, Y (Y is shown later.) Substituted phenylcarbonyl group having 1 to 5 substituents selected from, (C ₁ -C ₆₎ alkoxycarbonyl group, a carboxyl group Mono (C ₁ -C ₆ ) alkylaminocarbonyl group, which may be the same or different, di (C ₁ -C ₆ ) alkylaminocarbonyl group, phenylaminocarbonyl group, which may be the same or different, and Y (Y is described later) Shown in ) A substituted phenylaminocarbonyl group having 1 to 5 substituents selected from the above, a phenyl (C ₁ -C ₆ ) alkylaminocarbonyl group, which may be the same or different, and Y (Y is shown below) 1 to 4 selected from a substituted phenyl (C ₁ -C ₆ ) alkylaminocarbonyl group, hydroxyl group, amino group, cyano group or nitro group having 1 to 5 substituents selected from The substituent of is shown.

Y may be the same or different and is a halogen atom, (C ₁ -C ₆ ) alkyl group, (C ₂ -C ₆ ) alkenyl group, (C ₂ -C ₆ ) alkynyl group, cyclo (C ₃ -C ₆ ) Alkyl, halo (C ₁ -C ₆ ) alkyl, cyclohalo (C ₃ -C ₆ ) alkyl, (C ₁ -C ₆ ) alkoxy, halo (C ₁ -C ₆ ) alkoxy, (C _1- C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group, halo (C ₁ -C ₆ ) alkylsulfinyl group, (C ₁ -C ₆ ) alkylsulfonyl group Halo (C ₁ -C ₆ ) alkylsulfonyl group, phenyl group, which may be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, (C ₂ -C ₆ ) alkenyl group, (C _2- C ₆ ) alkynyl group, cyclo (C ₃ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, cyclohalo (C ₃ -C ₆ ) alkyl group, (C ₁ -C ₆ ) al Coxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group, halo (C ₁ -C ₆ ) alkylsulfinyl group, (C ₁ -C ₆ ) alkylsulfonyl group, halo (C ₁ -C ₆ ) alkylsulfonyl group, (C ₁ -C ₆ ) alkylcarbonyl group, halo (C ₁ -C ₆ ) Alkylcarbonyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, carboxyl group, mono (C ₁ -C ₆ ) alkylaminocarbonyl group, di (C ₁ -C ₆ ) alkylaminocarbonyl group which may be the same or different, A substituted phenyl group having 1 to 5 substituents selected from a hydroxyl group, an amino group, a cyano group or a nitro group, a heterocyclic group (the heterocyclic group is the same as above),

May be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, (C ₂ -C ₆ ) alkenyl group, (C ₂ -C ₆ ) alkynyl group, cyclo (C ₃ -C ₆ ) alkyl group , Halo (C ₁ -C ₆ ) alkyl group, cyclohalo (C ₃ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) Alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group, halo (C ₁ -C ₆ ) alkylsulfinyl group, (C ₁ -C ₆ ) alkylsulfonyl group, halo (C ₁ -C ₆ ) alkylsulfonyl group, (C ₁ -C ₆ ) alkylcarbonyl group, halo (C ₁ -C ₆ ) alkylcarbonyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, carboxyl group, mono ( C ₁ -C ₆₎ alkylaminocarbonyl group, the same or different and may di (C ₁ -C ₆₎ alkylaminocarbonyl group, water Group, an amino group, a substituted Hajime Tamaki having one or more substituents selected from cyano group or a nitro group (the heterocyclic group have the same meanings), a phenoxy group, which may be identical or different, halogen atoms, (C ₁ -C ₆ ) alkyl group, (C ₂ -C ₆ ) alkenyl group, (C ₂ -C ₆ ) alkynyl group, cyclo (C ₃ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, Cyclohalo (C ₃ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) An alkylthio group, a (C ₁ -C ₆ ) alkylsulfinyl group, a halo (C ₁ -C ₆ ) alkylsulfinyl group, a (C ₁ -C ₆ ) alkylsulfonyl group, a halo (C ₁ -C ₆ ) alkylsulfonyl group, ( C ₁ -C ₆₎ alkylcarbonyl group, halo (C ₁ -C ₆₎ alkylcarbonyl group, (C ₁ -C ₆₎ alkoxycarbonyl group Carboxyl group, a mono (C ₁ -C ₆₎ alkylaminocarbonyl group, the same or different and may di (C ₁ -C ₆₎ alkylaminocarbonyl group, a hydroxyl group, an amino group 1 is selected from a cyano group or a nitro group A substituted phenoxy group having 5 substituents, a phenylthio group,

May be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, (C ₂ -C ₆ ) alkenyl group, (C ₂ -C ₆ ) alkynyl group, cyclo (C ₃ -C ₆ ) alkyl group , Halo (C ₁ -C ₆ ) alkyl group, cyclohalo (C ₃ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) Alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group, halo (C ₁ -C ₆ ) alkylsulfinyl group, (C ₁ -C ₆ ) alkylsulfonyl group, halo (C ₁ -C ₆ ) alkylsulfonyl group, (C ₁ -C ₆ ) alkylcarbonyl group, halo (C ₁ -C ₆ ) alkylcarbonyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, carboxyl group, mono ( C ₁ -C ₆₎ alkylaminocarbonyl group, the same or different and may di (C ₁ -C ₆₎ alkylaminocarbonyl group, water Group, an amino group, a substituted phenylthio group having 1 to 5 substituents selected from cyano group or a nitro group, phenylsulfinyl group, the same or different and a halogen atom, (C ₁ -C ₆₎ alkyl group , (C ₂ -C ₆ ) alkenyl group, (C ₂ -C ₆ ) alkynyl group, cyclo (C ₃ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, cyclohalo (C ₃ -C ₆₎ ) Alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, (C _1- C ₆ ) alkylsulfinyl group, halo (C ₁ -C ₆ ) alkylsulfinyl group, (C ₁ -C ₆ ) alkylsulfonyl group, halo (C ₁ -C ₆ ) alkylsulfonyl group, (C ₁ -C ₆ ) alkyl carbonyl group, halo (C ₁ -C ₆₎ alkylcarbonyl group, (C ₁ -C ₆₎ alkoxycarbonyl group, Cal Hexyl group, a mono (C ₁ -C ₆₎ alkylaminocarbonyl group, the same or different and may di (C ₁ -C ₆₎ alkylaminocarbonyl group, a hydroxyl group, an amino group 1 is selected from a cyano group or a nitro group A substituted phenylsulfinyl group having 5 substituents, a phenylsulfonyl group, which may be the same or different, a halogen atom, a (C ₁ -C ₆ ) alkyl group, a (C ₂ -C ₆ ) alkenyl group, (C ₂ -C ₆ ) alkynyl group, cyclo (C ₃ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, cyclohalo (C ₃ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, Halo (C ₁ -C ₆ ) alkoxy, (C ₁ -C ₆ ) alkylthio, halo (C ₁ -C ₆ ) alkylthio, (C ₁ -C ₆ ) alkylsulfinyl, halo (C ₁ -C ₆ ) alkylsulfinyl groups, (C ₁ -C ₆₎ alkylsulfonyl groups, halo (C ₁ -C ₆₎ Al Rusuruhoniru group, (C ₁ -C ₆₎ alkylcarbonyl group, halo (C ₁ -C ₆₎ alkylcarbonyl group, (C ₁ -C ₆₎ alkoxycarbonyl group, a carboxyl group, a mono (C ₁ -C ₆₎ alkyl An aminocarbonyl group, a di (C ₁ -C ₆ ) alkylaminocarbonyl group which may be the same or different, a substituted phenylsulfonyl group having 1 to 5 substituents selected from a hydroxyl group, an amino group, a cyano group or a nitro group ,

(C ₁ -C ₆ ) alkylcarbonyl group, halo (C ₁ -C ₆ ) alkylcarbonyl group, phenylcarbonyl group, which may be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, (C ₂ -C ₆ ) alkenyl group, (C ₂ -C ₆ ) alkynyl group, cyclo (C ₃ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, cyclohalo (C ₃ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkyl Sulfinyl group, halo (C ₁ -C ₆ ) alkylsulfinyl group, (C ₁ -C ₆ ) alkylsulfonyl group, halo (C ₁ -C ₆ ) alkylsulfonyl group, (C ₁ -C ₆ ) alkylcarbonyl group, halo (C ₁ -C ₆ ) alkylcarbonyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, carboxyl group, mono (C ₁ -C ₆ ) a A substituted phenylcarbonyl having 1 to 5 substituents selected from an alkylaminocarbonyl group, a di (C ₁ -C ₆ ) alkylaminocarbonyl group which may be the same or different, a hydroxyl group, an amino group, a cyano group or a nitro group Group, (C ₁ -C ₆ ) alkoxycarbonyl group, carboxyl group, mono (C ₁ -C ₆ ) alkylaminocarbonyl group, di (C ₁ -C ₆ ) alkylaminocarbonyl group which may be the same or different, phenylamino Carbonyl group, which may be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, (C ₂ -C ₆ ) alkenyl group, (C ₂ -C ₆ ) alkynyl group, cyclo (C ₃ -C ₆₎ ) Alkyl group, halo (C ₁ -C ₆ ) alkyl group, cyclohalo (C ₃ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆₎ alkylthio groups, halo (C ₁ -C ₆₎ alkyl Oh group, (C ₁ -C ₆₎ alkylsulfinyl groups, halo (C ₁ -C ₆₎ alkylsulfinyl group, (C ₁ -C ₆₎ alkylsulfonyl groups, halo (C ₁ -C ₆₎ alkylsulfonyl groups, ( C ₁ -C ₆ ) alkylcarbonyl group, halo (C ₁ -C ₆ ) alkylcarbonyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, carboxyl group, mono (C ₁ -C ₆ ) alkylaminocarbonyl group, identical Or a substituted phenylaminocarbonyl group having 1 to 5 substituents selected from di (C ₁ -C ₆ ) alkylaminocarbonyl group, hydroxyl group, amino group, cyano group or nitro group, which may be different from each other,

Phenyl (C ₁ -C ₆ ) alkylaminocarbonyl group, which may be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, (C ₂ -C ₆ ) alkenyl group, (C ₂ -C ₆ ) Alkynyl, cyclo (C ₃ -C ₆ ) alkyl, halo (C ₁ -C ₆ ) alkyl, cyclohalo (C ₃ -C ₆ ) alkyl, (C ₁ -C ₆ ) alkoxy, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group, halo (C ₁ -C ₆ ) alkylsulfinyl group , (C ₁ -C ₆ ) alkylsulfonyl group, halo (C ₁ -C ₆ ) alkylsulfonyl group, (C ₁ -C ₆ ) alkylcarbonyl group, halo (C ₁ -C ₆ ) alkylcarbonyl group, (C ₁ -C ₆₎ alkoxycarbonyl group, a carboxyl group, a mono (C ₁ -C ₆₎ alkylaminocarbonyl group, the same or different Maintaining (C ₁ -C ₆₎ alkylaminocarbonyl group, a hydroxyl group, an amino group, a substituted phenyl (C ₁ -C ₆₎ alkyl having 1 to 5 substituents selected from cyano group or a nitro group on the ring 1 to 5 substituents selected from an aminocarbonyl group, a hydroxyl group, an amino group, a cyano group or a nitro group, and Y together with an adjacent carbon atom or nitrogen atom on the benzene ring or heterocyclic ring, It may be the same or different, and an oxygen atom, a sulfur atom or a nitrogen atom (the nitrogen atom is a hydrogen atom, a (C ₁ -C ₆ ) alkyl group, a (C ₂ -C ₆ ) alkenyl group, (C ₂ -C ₆ ) (Optionally substituted by an alkynyl group or a cyclo (C ₃ -C ₆ ) alkyl group.) (C ₁ -C ₄ ) alkylene group optionally interrupted by 1 or 2 heteroatoms (C ₁ -C ₄₎ alkylene group, (C ₂ -C ₄₎ alkenylene Group or a halo (C ₂ -C ₄₎ may form a 5- or 6-membered ring by an alkenylene group. }, A herbicide containing the compound as an active ingredient, and a method for using the herbicide.

｛式中、Ｒ¹はハロ（C₁-C₆）アルキル基を示す。
Ｒ³及びＲ⁴は同一又は異なっても良く、水素原子、（C₁-C₆）アルキル基、（C₃-C₆）シクロアルキル基、（C₁-C₆）アルコキシ基、ハロゲン原子又はシアノ基を示す。又、Ｒ³とＲ⁴はお互い結合して３〜７員環を形成することができる。
Ｒ⁵’は水素原子、（C₁-C₆）アルキル基、（C₃-C₆）シクロアルキル基、（C₁-C₆）アルコキシ基、ハロ（C₁-C₆）アルキル基、フェニル（C₁-C₆）アルキル基、同一又は異なっても良く、Ｙ’（Ｙ’は後記に示す。）から選択される１〜５個の置換基を環上に有する置換フェニル（C₁-C₆）アルキル基、フェニル基、同一又は異なっても良く、Ｙ’（Ｙ’は後記に示す。）から選択される１〜５個の置換基を有する置換フェニル基、複素環基（複素環基は前記に同じ。）、同一又は異なっても良く、Ｙ’（Ｙ’は後記に示す。）から選択される１以上の置換基を有する置換複素環基（複素環基は前記に同じ。）、（C₁-C₆）アルコキシカルボニル（C₁-C₆）アルキル基、フェノキシカルボニル（C₁-C₆）アルキル基、同一又は異なっても良く、Ｙ’（Ｙ’は後記に示す。）から選択される１〜５個の置換基を環上に有する置換フェノキシカルボニル（C₁-C₆）アルキル基、モノ（C₁-C₆）アルキルアミノカルボニル（C₁-C₆）アルキル基、同一又は異なっても良いジ（C₁-C₆）アルキルアミノカルボニル（C₁-C₆）アルキル基、フェニルアミノカルボニル（C₁-C₆）アルキル基、同一又は異なっても良く、Ｙ’（Ｙ’は後記に示す。）から選択される１〜５個の置換基を環上に有する置換フェニルアミノカルボニル（C₁-C₆）アルキル基、フェニル（C₁-C₆）アルキルアミノカルボニル（C₁-C₆）アルキル基又は同一若しくは異なっても良く、Ｙ’（Ｙ’は後記に示す。）から選択される１〜５個の置換基を環上に有する置換フェニル（C₁-C₆）アルキルアミノカルボニル（C₁-C₆）アルキル基を示す。 Furthermore, the present invention is an intermediate of the general formula (II)

{Wherein R ¹ represents a halo (C ₁ -C ₆ ) alkyl group.
R ³ and R ⁴ may be the same or different, and are a hydrogen atom, a (C ₁ -C ₆ ) alkyl group, a (C ₃ -C ₆ ) cycloalkyl group, a (C ₁ -C ₆ ) alkoxy group, a halogen atom or A cyano group is shown. R ³ and R ⁴ can be bonded to each other to form a ^3- to 7-membered ring.
R ⁵ ′ is a hydrogen atom, (C ₁ -C ₆ ) alkyl group, (C ₃ -C ₆ ) cycloalkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkyl group, phenyl (C ₁ -C ₆ ) alkyl group, which may be the same or different, substituted phenyl having 1 to 5 substituents selected from Y ′ (Y ′ is shown below) on the ring (C ₁ − C ₆ ) an alkyl group, a phenyl group, which may be the same or different, a substituted phenyl group having 1 to 5 substituents selected from Y ′ (Y ′ is shown below), a heterocyclic group (heterocycle) The groups may be the same or different, and may be the same or different, and a substituted heterocyclic group having one or more substituents selected from Y ′ (Y ′ will be described later) (the heterocyclic group is the same as above). ), (C ₁ -C ₆₎ alkoxycarbonyl (C ₁ -C ₆₎ alkyl group, phenoxycarbonyl (C ₁ -C ₆₎ alkyl group, which may be the same or different, Y ' Y 'is substituted phenoxycarbonyl (C ₁ -C ₆₎ alkyl group having from 1 to 5 substituents selected from the shown later.) On the ring, mono (C ₁ -C ₆₎ alkylaminocarbonyl (C ₁ -C ₆ ) alkyl group, di (C ₁ -C ₆ ) alkylaminocarbonyl (C ₁ -C ₆ ) alkyl group, phenylaminocarbonyl (C ₁ -C ₆ ) alkyl group, which may be the same or different, A substituted phenylaminocarbonyl (C ₁ -C ₆ ) alkyl group having 1 to 5 substituents selected from Y ′ (Y ′ is shown below) on the ring, phenyl (C ₁ -C ₆ ) alkylaminocarbonyl (C ₁ -C ₆ ) alkyl group, which may be the same or different, and each having 1 to 5 substituents selected from Y ′ (Y ′ is shown below) on the ring substituted phenyl having (C ₁ -C ₆₎ alkylaminocarbonyl (C ₁ -C ₆₎ alkyl group It is.

X ′ may be the same or different and is selected from a hydrogen atom, a halogen atom, a (C ₁ -C ₆ ) alkyl group or a (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group. Of substituents.
Y ′ may be the same or different, and is a halogen atom, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group, halo (C ₁ -C ₆ ) alkylsulfinyl group, ( C ₁ -C ₆ ) alkylsulfonyl group, halo (C ₁ -C ₆ ) alkylsulfonyl group, phenyl group, which may be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, halo (C _1- C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, substituted phenyl group having 1 to 5 substituents selected from cyano group or nitro group, ring group (heterocyclic group is as defined above.) may be the same or different, a halogen atom, (C ₁ -C ₆₎ alkyl group, a cycloalkyl C ₃ -C ₆₎ alkyl group, halo (C ₁ -C ₆₎ alkyl group, Shikuroharo (C ₃ -C ₆₎ alkyl group, (C ₁ -C ₆₎ alkoxy groups, halo (C ₁ -C ₆₎ alkoxy Group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group, halo (C ₁ -C ₆ ) alkylsulfinyl group, (C _1- C ₆ ) alkylsulfonyl group, halo (C ₁ -C ₆ ) alkylsulfonyl group, (C ₁ -C ₆ ) alkylcarbonyl group, halo (C ₁ -C ₆ ) alkylcarbonyl group, (C ₁ -C ₆ ) alkoxy carbonyl group, a carboxyl group selection, mono (C ₁ -C ₆₎ alkylaminocarbonyl group, the same or different and may di (C ₁ -C ₆₎ alkylaminocarbonyl group, a hydroxyl group, an amino group, a cyano group or a nitro group A substituted heterocyclic group having one or more substituents (the heterocyclic group is the same as described above), Alkoxy group, which may be identical or different, halogen atom, (C ₁ -C ₆₎ alkyl group, halo (C ₁ -C ₆₎ alkyl group, (C ₁ -C ₆₎ alkoxy groups, halo (C ₁ -C ₆ ) a substituted phenoxy group having 1 to 5 substituents selected from an alkoxy group, a cyano group or a nitro group,

Phenylthio group, which may be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) A substituted phenylthio group having 1 to 5 substituents selected from an alkoxy group, a cyano group or a nitro group, a phenylsulfinyl group, which may be the same or different, a halogen atom, a (C ₁ -C ₆ ) alkyl group ₁ to 5 substituents selected from halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, cyano group or nitro group Substituted phenylsulfinyl group, phenylsulfonyl group, which may be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group , Halo (C ₁ -C ₆ ) alkoxy, cyano or nitro A substituted phenylsulfonyl group having 1 to 5 selected substituents, a (C ₁ -C ₆ ) alkylcarbonyl group, a halo (C ₁ -C ₆ ) alkylcarbonyl group, a phenylcarbonyl group, which may be the same or different , Halogen atom, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, cyano group or nitro A substituted phenylcarbonyl group having 1 to 5 substituents selected from the group, (C ₁ -C ₆ ) alkoxycarbonyl group, carboxyl group, mono (C ₁ -C ₆ ) alkylaminocarbonyl group, the same or different Di (C ₁ -C ₆ ) alkylaminocarbonyl group, phenylaminocarbonyl group, which may be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group , (C ₁ -C ₆₎ alkoxy groups, halo C ₁ -C ₆₎ alkoxy group, 1 to 5 substituents a substituted phenylaminocarbonyl group having on the ring, phenyl (C ₁ -C ₆₎ alkylaminocarbonyl group selected from cyano group or a nitro group, the same Or may be different, halogen atom, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group 1 to 5 selected from a substituted phenyl (C ₁ -C ₆ ) alkylaminocarbonyl group, cyano group or nitro group having 1 to 5 substituents selected from a cyano group or a nitro group on the ring Y ′ represents a substituent, and Y ′ may be the same or different together with an adjacent carbon atom or nitrogen atom on the benzene ring or heterocyclic ring, and an oxygen atom, a sulfur atom or a nitrogen atom (the nitrogen atom is a hydrogen atom) , (C ₁ -C ₆ ) alkyl groups, (C ₂ -C ₆ ) al It may be substituted by a kenyl group, a (C ₂ -C ₆ ) alkynyl group or a cyclo (C ₃ -C ₆ ) alkyl group. Or a (C ₁ -C ₄ ) alkylene group which may be interrupted by 1 or 2 heteroatoms selected from:
However, a compound in which X ′ is a hydrogen atom, R ¹ is CF ₃ , the substitution position of R ¹ SO ₂ NH is 4-position, and R ³ , R ^4, and R ⁵ ′ are hydrogen atoms is excluded. } Or a salt thereof.

The present invention provides a herbicide that is excellent in safety for human livestock, has high crop selectivity, and exhibits a high herbicidal effect at a low dosage, so that it not only improves the efficiency of farm work but also reduces the environmental burden.

In the definition of the general formula (I) of the haloalkylsulfonanilide derivative of the present invention, the “halogen atom” refers to a chlorine atom, a bromine atom, an iodine atom or a fluorine atom. “(C ₁ -C ₆ ) alkylene group” means a linear or branched alkylene group having 1 to 6 carbon atoms such as methylene, ethylene, propylene, dimethylmethylene, tetramethylene, isobutylene, dimethylethylene, hexamethylene, etc. And “(C ₂ -C ₆ ) alkenylene group” represents a linear or branched alkenylene group having 2 to 6 carbon atoms. The “(C ₁ -C ₆ ) alkyl group” means, for example, straight or branched chain such as methyl, ethyl, normal propyl, isopropyl, normal butyl, isobutyl, secondary butyl, tertiary butyl, normal pentyl, neopentyl, normal hexyl, etc. An alkyl group having 1 to 6 carbon atoms. The “halo (C ₁ -C ₆ ) alkyl group” refers to a linear or branched alkyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different, For example, trifluoromethyl, difluoromethyl, perfluoroethyl, perfluoroisopropyl, chloromethyl, bromomethyl, 1-bromoethyl, 2,3-dibromopropyl and the like are shown. “Fluoro (C ₁ -C ₆ ) alkyl group” means a linear or branched alkyl group having 1 to 6 carbon atoms substituted with one or more fluorine atoms which may be the same or different; For example, trifluoromethyl, difluoromethyl, perfluoroethyl, perfluoroisopropyl, perfluorohexyl and the like are shown. The “(C ₃ -C ₆ ) cycloalkyl group” means an alicyclic alkyl group having 3 to 6 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 2-methylcyclopropyl, 2-methylcyclopentyl and the like. Show.

“(C ₁ -C ₆ ) alkoxy group” means, for example, methoxy, ethoxy, normal propoxy, isopropoxy, normal butoxy, secondary butoxy, tertiary butoxy, normal pentyloxy, isopentyloxy, neopentyloxy, normal hexyloxy A linear or branched alkoxy group having 1 to 6 carbon atoms such as The “halo (C ₁ -C ₆ ) alkoxy group” refers to a linear or branched alkyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different, For example, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy and the like are shown. The “(C ₁ -C ₆ ) alkoxycarbonyl group” means, for example, linear or branched carbon atoms such as methoxycarbonyl, ethoxycarbonyl, normalpropoxycarbonyl, isopropoxycarbonyl, normal butoxycarbonyl, tertiary butoxycarbonyl, etc. 1-6 alkoxycarbonyl groups are shown. “(C ₁ -C ₆ ) alkylthio group” means, for example, methylthio, ethylthio, normalpropylthio, isopropylthio, normal butylthio, secondary butylthio, tertiary butylthio, normal pentylthio, isopentylthio, normal hexylthio A linear or branched alkylthio group having 1 to 6 carbon atoms is shown. “(C ₁ -C ₆ ) alkylsulfinyl group” means, for example, methylsulfinyl, ethylsulfinyl, normalpropylsulfinyl, isopropylsulfinyl, normalbutylsulfinyl, secondary butylsulfinyl, tertiary butylsulfinyl, normalpentylsulfinyl, isopentylsulfinyl, A linear or branched alkylsulfinyl group having 1 to 6 carbon atoms, such as normal hexylsulfinyl. “(C ₁ -C ₆ ) alkylsulfonyl” means, for example, methylsulfonyl, ethylsulfonyl, normalpropylsulfonyl, isopropylsulfonyl, normalbutylsulfonyl, secondary butylsulfonyl, tertiary butylsulfonyl, normal pentylsulfonyl, isopentylsulfonyl, A linear or branched alkylsulfonyl group having 1 to 6 carbon atoms such as normal hexylsulfonyl is shown.

Examples of the salt of the haloalkylsulfonamide derivative represented by the general formula (I) or the benzylamine derivative represented by the general formula (II) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate. Organic salts such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, paratoluenesulfonate, salts with sodium ion, potassium ion, calcium ion, etc. It can be illustrated.
The haloalkylsulfonanilide derivative represented by the general formula (I) of the present invention may contain one or more asymmetric centers in the structural formula, and two or more optical isomers and diastereomers may be present. Although it may exist, the present invention includes all of the optical isomers and the mixtures in which they are contained in an arbitrary ratio. In addition, the haloalkylsulfonanilide derivative represented by the general formula (I) of the present invention has two geometric isomers derived from a carbon-carbon double bond or a carbon-nitrogen double bond in the structural formula. In some cases, the present invention also encompasses all geometric isomers and mixtures containing them in any proportion.
The typical production methods of the present invention are schematically shown below, but the present invention is not limited to these.

（式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｘ、Ｇ、Ｑ、ａ及びｂは前記に同じくし、Ｌはハロゲン原子等の脱離基を示す。） Manufacturing method 1
Among the haloalkylsulfonamide derivatives represented by the general formula (I), a compound in which A is an oxygen atom can be produced by the following production method.

(Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X, G, Q, a and b are the same as above, and L is a leaving group such as a halogen atom) Show.)

An acid halogen represented by the general formula (III) in the presence or absence of an inert solvent using a compound represented by the general formula (II ′) in the presence of a base and, if necessary, a phase transfer catalyst. Or a compound represented by the general formula (II ′) in the presence of a condensing agent, if necessary, in the presence or absence of an inert solvent. By reacting with a carboxylic acid derivative represented by the general formula (III ′), a compound represented by the general formula (IV-1) is obtained.
By reducing the nitro group in the presence or absence of an inert solvent with or without isolating the compound, the amino compound represented by the general formula (V-1) is obtained, and the compound is simply Reacting with a haloalkylsulfonyl derivative represented by R ¹ SO ₂ -L or (R ¹ SO ₂ ) ₂ O in the presence of a base, in the presence or absence of an inert solvent, without separation or isolation. Thus, the compound of the present invention represented by the general formula (I-1) can be produced. Furthermore, the general formula (I-
A compound represented by 1) not separated or single isolation, the presence of a base, using a phase transfer catalyst, if necessary the general formula R ² -L in the presence or absence of an inert solvent This invention compound represented by general formula (I-2) can be manufactured by making the compound represented by these react.

(1-1) General formula (II ′) → General formula (IV-1)
The starting compound of the general formula (II ′) can be obtained from known literature {eg Rev. Roum. Chim., 34 (7), 1607 (1989), Tetrahedron Lett., 2691 (1970), J. Heterocycl. Chem. , 25, 789 (1988), J. Am. Chem. Soc., 93, 2897 (1971), J. Org. Chem., 28, 3259 (1963), etc.} Can be manufactured. Compounds of general formula (III) or (III ′) are known literatures {eg J. Org. Chem., 26, 1003 (1961), Org. Synth., 32, 92 (1952), Tetrahedron lett., 1383. (1972), J. Chem. Soc. Chem. Commun., 229 (1976), etc.} or according to these methods.

The inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit this reaction, and examples thereof include chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane, and aromatic carbonization such as benzene, toluene, and xylene. Hydrogens, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, nitriles such as acetonitrile, esters such as ethyl acetate, N, N- Inert solvents such as dimethylformamide, amides such as N, N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone and water can be exemplified, and these inert solvents can be used alone or Two or more kinds can be mixed and used.
Examples of the base that can be used in this reaction include nitrogen-containing organic bases such as triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] -7-undecene, pyridine, sodium carbonate, potassium carbonate, sodium bicarbonate. Inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride and metallic sodium, organic bases such as sodium acetate and potassium acetate, alcoholates such as sodium ethoxide and potassium t-butoxide, etc. it can. The base may be used in an amount sufficient to neutralize the acid generated by the reaction, but an excessive amount can be used.

Examples of the phase transfer catalyst that can be used in this reaction include quaternary ammonium salts such as tetra n-butylammonium bromide and benzyltriethylammonium bromide, and crown ethers such as 18-crown-6. What is necessary is just to select the usage-amount of a phase transfer catalyst suitably from the range of 0.01-0.5 times mole with respect to the compound represented by general formula (II ').
Examples of the condensing agent that can be used in this reaction include carbodiimides such as 1,3-dicyclohexylcarbodiimide, 1,3-diisopropylcarbodiimide, 1-ethyl-3- (3′-dimethylaminopropyl) carbodiimide hydrochloride, N, Examples include N'-carbonyldiimidazole, 2-chloro-1-methylpyridinium iodide, diethyl phosphorocyanidate, phosphoric acid dichloride phenyl ester, cyanuric chloride, isobutyl chloroformate, chlorosulfonyl isocyanate, trifluoroacetic anhydride, etc. can do. What is necessary is just to select the usage-amount of a condensing agent suitably from the range of 1-5 times mole with respect to the compound represented by general formula (II ').
Since this reaction is an equimolar reaction, each reactant may be used in an equimolar amount, but any of the reactants can be used in excess. The reaction temperature can be carried out in the range of −20 ° C. to the reflux temperature of the inert solvent to be used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected in the range of several minutes to 48 hours. .
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary. Moreover, it can also use for next reaction, without isolating a target object after completion | finish of this reaction.

(1-2) General formula (IV-1) → General formula (V-1)
Examples of the inert solvent that can be used in this reaction include alcohols such as methanol and ethanol, ethers such as tetrahydrofuran and dioxane, water, and the like. These inert solvents can be used alone or in combination of two or more. Can be used. Moreover, the aqueous solution of the acid used as the reducing agent shown below can be used as an inert solvent as it is.
Examples of the reducing agent that can be used in this reaction include metal-acids, metal-salts, and the like. Examples of metals include iron, tin, and zinc. Examples of acids include mineral acids such as hydrochloric acid and sulfuric acid. Examples of salts of organic acids such as acetic acid, tin chloride, etc. include ammonium chloride. Moreover, it is also possible to use these in combination.
The amount of the reducing agent to be used is appropriately selected from the range of 1 to 10 times mol of the metal and 0.05 to 10 times mol of the acid and salt with respect to the compound represented by the general formula (IV-1). It ’s fine. The reaction temperature may be selected from the range of 0 to 150 ° C., and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within the range of several minutes to 48 hours.
The reduction reaction can also be carried out by a catalytic hydrogenation method in the presence of a catalyst. Examples of the catalyst include palladium carbon, platinum, Raney nickel and the like.
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary. Moreover, it can also use for next reaction, without isolating a target object after completion | finish of this reaction.

(1-3) General formula (V-1) → General formula (I-1)
This reaction can be carried out according to (1-1).
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary. Moreover, it can also use for next reaction, without isolating a target object after completion | finish of this reaction.

(1-4) General formula (I-1) → General formula (I-2)
This reaction can be carried out according to (1-1).
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary.

（式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｘ、Ｇ、Ｑ、Ｌ、ａ及びｂは前記に同じ。） Manufacturing method 2
Among the compounds represented by the general formula (I), a compound in which A is a sulfur atom can be produced by the following production method.

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X, G, Q, L, a and b are the same as above.)

A thioamide derivative represented by the general formula (IV-2) by reacting the compound represented by the general formula (IV-1) with a sulfurizing agent such as a Lawson reagent in the presence or absence of an inert solvent. The amino compound represented by the general formula (V-2) is obtained by reducing the nitro group in the presence or absence of an inert solvent, with or without isolating the compound. The haloalkylsulfonyl derivative represented by R ¹ SO ₂ -L or (R ¹ SO ₂ ) ₂ O is reacted with or without isolation in the presence of a base, in the presence or absence of an inert solvent. By making it, this invention compound represented by general formula (I-3) can be manufactured. Furthermore, the general formula (
The compound represented by I-3) is represented by the general formula R ^{2 in the} presence or absence of an inert solvent in the presence or absence of a base and optionally using a phase transfer catalyst. The compound of the present invention represented by the general formula (I-4) can be produced by reacting the compound represented by -L.

(2-1) General formula (IV-1) → General formula (IV-2)
The inert solvent that can be used in the present reaction is not particularly limited as long as it does not significantly inhibit the progress of the present reaction. Inert solvents such as aromatic hydrocarbons, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, and halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, can be exemplified. A solvent can be used individually or in mixture of 2 or more types.
As a sulfurizing agent that can be used in this reaction, for example, 2,4-bis (4-methoxyphenyl) -1,3,4,4-dithiadiphosphetane-2,4-disulfide known as Lawesson's reagent is used. Etc. can be illustrated. The amount of the sulfurizing agent used may be appropriately selected from the range of 0.5 to 5 moles relative to the compound represented by the general formula (IV-1). The reaction temperature may be selected from the range of 0 to 150 ° C., and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within the range of several minutes to 48 hours.
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary. Moreover, it can also use for next reaction, without isolating a target object after completion | finish of this reaction.

(2-2) General formula (IV-2) → General formula (V-2)
This reaction can be carried out according to (1-2).
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary. Moreover, it can also use for next reaction, without isolating a target object after completion | finish of this reaction.

(2-3) General formula (V-2) → General formula (I-3)
This reaction can be carried out according to (1-3).
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary. Moreover, it can also use for next reaction, without isolating a target object after completion | finish of this reaction.

(2-4) General formula (I-3) → General formula (I-4)
This reaction can be carried out according to (1-4).
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary.

（式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵’、Ｒ⁶、Ｒ⁷、Ｘ’、Ｇ、Ｑ、Ｌ、ａ及びｂは前記に同じ。） Manufacturing method 3
The compound of the present invention can also be produced by the following production method using the compound represented by the general formula (II) as a starting material.

(Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ ′, R ⁶ , R ⁷ , X ′, G, Q, L, a and b are the same as above)

An acid halide represented by the general formula (III) in the presence or absence of an inert solvent using a phase transfer catalyst in the presence of a base, if necessary, in the presence of a base. Or by reacting with an acid anhydride, or in the presence or absence of an inert solvent, the compound represented by the general formula (II) is used in the presence of a condensing agent, if necessary, in the presence of an inert solvent. By reacting with the carboxylic acid derivative represented by (III ′), the compound of the present invention represented by the general formula (I-5) can be produced. Further, the compound represented by the general formula (I-5) is isolated or not isolated, and in the presence of a base, optionally using a phase transfer catalyst, in the presence or absence of an inert solvent. The compound of the present invention represented by the general formula (I-6) can be produced by reacting the compound represented by the general formula R ² -L. Furthermore, by reacting a sulfurizing agent such as Lawson's reagent in the presence or absence of an inert solvent with or without isolating the compound represented by the general formula (I-6), The compound of the present invention represented by I-8) can be produced.
Further, by reacting a sulfurizing agent such as Lawson's reagent in the presence or absence of an inert solvent with or without isolating the compound represented by the general formula (I-5), the general formula (I-7
This invention compound represented by this can be manufactured. Further, the compound represented by the general formula (I-7) is isolated or not isolated, and in the presence of a base, optionally using a phase transfer catalyst, in the presence or absence of an inert solvent. The compound of the present invention represented by the general formula (I-8) can be produced by reacting the compound represented by the general formula R ² -L.

(3-1) General formula (II) → General formula (I-5)
Although the compound of the general formula (II) which is a starting material is a novel compound, it can be produced according to a method described in known literature {for example, J. Med. Chem., 46, 3116 (2003)}.
This reaction can be carried out according to (1-1).
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary. Moreover, it can also use for next reaction, without isolating a target object after completion | finish of this reaction.

(3-2) General formula (I-5) → General formula (I-6)
This reaction can be carried out according to (1-4).
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary. Moreover, it can also use for next reaction, without isolating a target object after completion | finish of this reaction.

(3-3) General formula (I-5) → General formula (I-7)
This reaction can be carried out according to (2-1).
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary. Moreover, it can also use for next reaction, without isolating a target object after completion | finish of this reaction.

(3-4) General formula (I-6) → General formula (I-8)
This reaction can be carried out according to (2-1).
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary.

(3-5) General formula (I-7) → General formula (I-8)
This reaction can be carried out according to (1-4).
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary.

「置換位置」は各々の構造式において、ベンゼン環上のハロアルキルスルホニルアミノ基、ニトロ基又はアミノ基の置換位置を示す。 Representative examples of haloalkylsulfonanilide derivatives represented by the general formula (I) of the present invention are shown in Tables 1 to 3 as intermediates represented by the general formula (IV-1) or (IV-2). In Tables 4 and 5, intermediates represented by general formula (V-1) or (V-2) in Tables 6 and 7, intermediates represented by general formula (II) Are shown in Table 8, but the present invention is not limited thereto. In Tables 1 to 8, physical properties indicate melting point (° C.) or refractive index. Table 1 shows the ¹ H-NMR spectrum data of the compounds whose physical properties in Tables 1 to 8 are described as NMR.
In the following table, “Me” represents a methyl group, “Et” represents an ethyl group, “Pr” represents a propyl group, “Bu” represents a butyl group, “Hex” represents a hexyl group, and “Ph” represents a phenyl group. "Bn" is a benzyl group, "Pyn" is a pyridyl group, "Pym" is a pyrimidyl group, "Ac" is an acetyl group, "n-" is normal, and "i-" is iso. , “T-” represents tertiary, and “c-” represents an alicyclic hydrocarbon group. “C-pentapyrazole” represents the following structure.

“Substitutional position” indicates the substitution position of the haloalkylsulfonylamino group, nitro group or amino group on the benzene ring in each structural formula.

  The herbicides containing the haloalkylsulfonanilide derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient are, for example, Inobie (1st grade Gramineae, pests of paddy field), Tamagayatsuri (1st graded Crassaceae 1st grade grass) , Paddy field (weed perennials), pine beetle (perennials of periwinkle), wetlands, waterways, paddy fields, perennial damage of paddy fields), urikawa (perennials, paddy fields, wetlands, perennial pests), firefly Perennial grass, paddy field, wetland, ditch), sparrow rotifer (occurrence in rice perennial grass, paddy backland, low wetland), oat grass (occurrence in perennial grass, flatland, wasteland, upland), mugwort (Chrysanthemum) Perennial grasses, occurring in wild fields, field), Japanese barnyard grass (Gramineous annual grasses, field, horticultural grass), Gishigishi (perennial perennial grasses, growing in field, roadside), Kogomegayatsu (Cyperaceae 1st year grass, field grass damage), Aoyu (Amarida 1st year grass, vacant land, roadside, upland field), Onamomi (Asteraceae 1st grade grass, field grass), Ichibi (1 year old mallow) Grass, upland grass, upland grass, 1st grade solanaceous grass, upland grass, green grass, perennial grass, upland grass, upland grass, upland field, It is useful for weeding annual, perennial and perennial weeds occurring in paddy fields, fields, orchards, wetlands, etc. In particular, it is effective for controlling weeds in paddy fields, and has a wide range of selectivity between rice and paddy weeds, and therefore has excellent performance as a herbicide for paddy fields.

Since the herbicide containing the haloalkylsulfonanilide derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient exhibits an excellent herbicidal effect on weeds before emergence and after emergence, Features of the herbicide of the present invention by treating the planting site in advance, or after planting a useful plant (including when the useful plant has already been planted like an orchard) from the beginning to the growing stage of weeds A certain physiological activity can be effectively expressed. However, the herbicide of the present invention should not be used only in such an embodiment. For example, the herbicide of the present invention can be used not only as a herbicide for paddy fields but also as a herbicide for general weeds. Eliminating general weeds such as cuts, cultivated fields, fallow fields, farm roads, waterways, pastures, cemeteries, parks, roads, playgrounds, vacant lots around buildings, open land, track ends, forests, etc. Can also be used for. In this case, it is economically most effective to carry out the treatment before the beginning of weed generation, but it is not necessarily limited to this, and it is possible to control weeds in the growing season.
When the haloalkylsulfonanilide derivative represented by the general formula (I) of the present invention or a salt thereof is used as a herbicide, it is generally used in a convenient form for use according to a conventional method for agricultural chemical formulations. Is. That is, the haloalkylsulfonanilide derivative represented by the general formula (I) of the present invention or a salt thereof is blended in a suitable ratio with a suitable inert carrier or, if necessary, an auxiliary agent. Dissolve, separate, suspend, mix, impregnate, adsorb or adhere, appropriate dosage form such as suspension, milk suspension, emulsion, liquid, wettable powder, granule, powder, tablet, jumbo, pack What is necessary is just to formulate and use for an agent.

The inert carrier that can be used in the present invention may be either solid or liquid. Examples of materials that can be used as a solid carrier include vegetable powders (for example, soybean flour, cereal flour, wood flour, bark flour, Sawdust, tobacco stem powder, walnut shell powder, bran, fiber powder, residues after extraction of plant extracts), synthetic polymers such as pulverized synthetic resin, clays (eg kaolin, bentonite, acid clay), talc (For example, talc, pyrophyllite, etc.), silicas {for example, diatomaceous earth, silica sand, mica, white carbon (some synthetic high-dispersion silicic acid also called hydrous fine silicon or hydrous silicic acid, and some products contain calcium silicate as a main component)} , Activated carbon, natural minerals (eg sulfur powder, pumice, attapulgite and zeolite), calcined diatomaceous earth, brick ground, fly ash, sand, plus For example, inorganic carrier powder such as calcium carbonate, calcium phosphate, chemical fertilizer such as ammonium sulfate, phosphate, ammonium nitrate, urea, ammonium sulfate, compost, etc. These can be used alone or in the form of a mixture of two or more.
The material that can be used as a liquid carrier is selected from those having solvent ability itself, and those that can disperse an active ingredient compound with the aid of an auxiliary agent without having solvent ability. The following carriers can be exemplified, but these are used alone or in the form of a mixture of two or more thereof, for example, water, alcohols (for example, methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.), ketones (for example, acetone) , Methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.), ethers (eg, ethyl ether, dioxane, cellosolve, dipropyl ether, tetrahydrofuran, etc.), aliphatic hydrocarbons (eg, kerosene, mineral oil, etc.), aromatic Group hydrocarbons (eg benzene, tolue , Xylene, solvent naphtha, alkylnaphthalene, etc.), halogenated hydrocarbons (eg, dichloroethane, chloroform, carbon tetrachloride, etc.), esters (eg, ethyl acetate, diisopropylpropyl phthalate, dibutyl phthalate, dioctyl phthalate, etc.), amides (For example, dimethylformamide, diethylformamide, dimethylacetamide and the like), nitriles (for example, acetonitrile and the like), dimethylsulfoxides and the like can be mentioned.

As other adjuvants, the following typical adjuvants can be mentioned, and these adjuvants are used depending on the purpose and are used alone, or in some cases, two or more kinds of adjuvants are used together. In some cases it is possible to use no adjuvants at all. Surfactants are used for the purpose of emulsifying, dispersing, solubilizing and / or wetting of the active ingredient compound, such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene higher fatty acid ester, polyoxyethylene. Examples of surfactants such as resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylaryl sulfonate, naphthalene sulfonate condensate, lignin sulfonate, higher alcohol sulfate Can do.
In addition, for the purpose of stabilizing the dispersion of the active ingredient compound, adhesion and / or binding, the following auxiliary agents can be used, for example, casein, gelatin, starch, methylcellulose, carboxymethylcellulose, gum arabic, polyvinyl Adjuvants such as alcohol, pine oil, coconut oil, bentonite and lignin sulfonate can also be used. In order to improve the fluidity of the solid product, the following adjuvants can also be used, and for example, adjuvants such as waxes, stearates and alkyl phosphates can be used. As a peptizer for a suspension product, for example, auxiliary agents such as naphthalenesulfonic acid condensate and condensed phosphate can be used. As the antifoaming agent, for example, an auxiliary agent such as silicone oil can be used.

The blending ratio of the active ingredient compound can be adjusted as necessary and is not particularly limited. However, the lower limit is about 0.001% by weight to the upper limit is about 90% by weight, preferably, for example, a powder or a granule. The lower limit is about 0.01% by weight, more preferably about 0.1% by weight, and the upper limit is about 50% by weight, more preferably about 10% by weight. Emulsions, wettable powders or granular wettable powders are used. The lower limit in this case is about 0.01% by weight, more preferably about 0.1% by weight, and the upper limit is about 90% by weight, more preferably about 60% by weight. The herbicide containing the haloalkylsulfonanilide derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient is diluted as it is or appropriately with water or the like in order to kill or suppress growth of various weeds. Alternatively, an amount effective for controlling slaughtering or growth in a suspended form may be applied to the weeds or to the foliage or soil in a place where the generation or growth of the weeds is not preferred.
The amount of herbicide containing the haloalkylsulfonanilide derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient is various factors such as the purpose, the target weed, the growth status of the crop, the tendency of weed generation. Depending on the weather, environmental conditions, dosage form, application method, application location, application time, etc., the active ingredient compound may be appropriately selected from the range of 0.1 g to 10 kg per hectare according to the purpose. The herbicide containing the haloalkylsulfonanilide derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient is further used for controlling the weeds to be controlled, for the expansion of the control period, or for the purpose of reducing the dosage. It is also possible to use it in combination with other herbicides.

Example 1
(1-1) Synthesis of N-methyl-N- (2-nitrobenzyl) -4-chlorobenzamide (Compound No. 4-20) (2-nitrobenzyl) methylamine (0.5 g, 3.0 mmol) Was dissolved in tetrahydrofuran (10 ml), and the reaction solution was cooled to 0 ° C. Then 4-chlorobenzoic acid (0.6 g, 3.2 mmol) was added dropwise in 2 minutes. The mixture was stirred at the same temperature for 2 hours, and further stirred for 1 hour while gradually raising the reaction temperature to room temperature. Water (10 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed once with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off. N-methyl-N- (2-nitrobenzyl) -4-chlorobenzamide (0.8 g, yield) 88%). The melting point was 80.6 ° C.

(1-2) Synthesis of N- (2-aminobenzyl) -N-methyl-4-chlorobenzamide (Compound No. 6-19) N-methyl-N- (2-nitrobenzyl) -4-chlorobenzamide ( 0.5 g, 1.6 mmol), iron powder (0.5 g, 8.0 mmol), ammonium chloride (0.04 g, 0.8 mmol) were dissolved in ethanol (10 ml) and water (5 ml). Heated to reflux for hours. After cooling to room temperature, the reaction mixture was filtered with suction and extracted with ethyl acetate. The ethyl acetate layer was washed once with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off. N- (2-aminobenzyl) -N-methyl-4-chlorobenzamide (0.4 g, yield) 100%). The refractive index was 1.6042 (20 ° C.).

(1-3) Synthesis of N-methyl-N- (2-trifluoromethanesulfonylaminobenzyl) -4-chlorobenzamide (Compound No. 1-24) N- (2-aminobenzyl) -N-methyl-4- Chlorobenzamide (0.4 g, 1.6 mmol) and triethylamine (0.2 g, 1.6 mmol) were dissolved in chloroform (10 ml), and then the reaction solution was cooled to −10 ° C. Subsequently, a solution obtained by diluting trifluoromethanesulfonic anhydride (0.5 g, 1.6 mmol) with 0.5 ml of chloroform was added dropwise over 2 minutes. After stirring at the same temperature for 2 hours, the reaction temperature was gradually raised to room temperature and further stirred for 10 hours. After completion of the reaction, chloroform was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography. N-methyl-N- (2-trifluoromethanesulfonylaminobenzyl) -4-chlorobenzamide (0.4 g, yield) 60%). The melting point was 112.0-112.5 ° C.

Example 2
(2-1) Synthesis of N-methyl-N- (2-nitrobenzyl) -1-phenyl-1-cyclopropanecarboxamide (Compound No. 5-16) 1-phenyl-1-cyclopropanecarboxylic acid (1. 1 g, 6.6 mmol) was dissolved in tetrahydrofuran (20 ml) at room temperature, then 2-chloro-1-methylpyridinium iodide (1.8 g, 7.7 mmol), triethylamine (1.5 g, 15.1). Mmol), (2-nitrobenzyl) methylamine (1.0 g, 6.0 mmol) was added. After stirring at the same temperature for 21 hours, water (20 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed once with 1N hydrochloric acid, dried over anhydrous sodium sulfate, and the solvent was distilled off. N-methyl-N- (2-nitrobenzyl) -1-phenyl-1-cyclopropanecarboxamide (1 0.9 g, yield 100%). The refractive index was 1.5834 (25 ° C.).

(2-2) Synthesis of N- (2-aminobenzyl) -N-methyl-1-phenyl-1-cyclopropanecarboxamide (Compound No. 7-16) N-methyl-N- (2-nitrobenzyl)- 1-Phenyl-1-cyclopropanecarboxamide (1.9 g, 6.0 mmol), iron powder (1.7 g, 30.2 mmol), ammonium chloride (0.2 g, 3.0 mmol) in ethanol (40 ml) And water (20 ml) and heated to reflux for 2 hours. After cooling to room temperature, the reaction mixture was filtered with suction and extracted with ethyl acetate. The ethyl acetate layer was washed once with saturated brine, dried over anhydrous sodium sulfate, the solvent was distilled off, and the precipitated crystals were washed with a mixed solution of hexane-diethyl ether (1: 1), filtered and dried. N- (2-aminobenzyl) -N-methyl-1-phenyl-1-cyclopropanecarboxamide (1.4 g, 84% yield) was obtained. The melting point was 79.1-79.3 ° C.

(2-3) Synthesis of N-methyl-N- (2-trifluoromethanesulfonylaminobenzyl) -1-phenyl-1-cyclopropanecarboxamide (Compound No. 2-17) N- (2-aminobenzyl) -N -Methyl-1-phenyl-1-cyclopropanecarboxamide (1.4 g, 5.1 mmol) and triethylamine (0.5 g, 5.3 mmol) were dissolved in chloroform (30 ml). Cooled to. Then, a solution obtained by diluting trifluoromethanesulfonic anhydride (1.4 g, 5.1 mmol) with 0.5 ml of chloroform was added dropwise over 2 minutes. After stirring at the same temperature for 2 hours, the reaction temperature was gradually raised to room temperature and further stirred for 10 hours. After completion of the reaction, chloroform was distilled off under reduced pressure, the residue was purified by silica gel column chromatography, and N-methyl-N- (2-trifluoromethanesulfonylaminobenzyl) -1-phenyl-1-cyclopropanecarboxamide ( 1.8 g, yield 88%). The melting point was 92.7-92.8 ° C.

Example 3
(3-1) Synthesis of N-methyl-N- (2-nitrobenzyl) -2-phenoxypropionamide (Compound No. 5-31) 2-Phenoxypropionic acid (0.3 g, 1.7 mmol) was added at room temperature. In tetrahydrofuran (15 ml), then 2-chloro-1-methylpyridinium iodide (0.5 g, 1.9 mmol), triethylamine (0.4 g, 4.0 mmol), (2-nitrobenzyl) Methylamine (0.3 g, 1.6 mmol) was added. After stirring at the same temperature for 3 hours, water (20 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed once with 1N hydrochloric acid, dried over anhydrous sodium sulfate, and the solvent was distilled off. N-methyl-N- (2-nitrobenzyl) -2-phenoxypropionamide (0.5 g, yield) 100%). The refractive index was 1.5680 (27 ° C.).

(3-2) Synthesis of N- (2-aminobenzyl) -N-methyl-2-phenoxypropionamide (Compound No. 7-32) N-methyl-N- (2-nitrobenzyl) -2-phenoxypropion The product was dissolved in amide (0.5 g, 1.6 mmol), iron powder (0.3 g, 4.8 mmol), ethyl acetate (10 ml), acetic acid (3 ml) and water (3 ml), and heated to reflux for 2 hours. After cooling to room temperature, the reaction mixture was filtered with suction, saturated aqueous sodium hydrogen carbonate solution was added to adjust the pH to 8, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed once with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off. N- (2-aminobenzyl) -N-methyl-2-phenoxypropionamide (0.5 g, collected) 100%). The refractive index was 1.5700 (27 ° C.).

(3-3) Synthesis of N-methyl-N- (2-trifluoromethanesulfonylaminobenzyl) -2-phenoxypropionamide (Compound No. 2-33) N- (2-aminobenzyl) -N-methyl-2 -After dissolving phenoxypropionamide (0.5 g, 1.6 mmol) and triethylamine (0.2 g, 1.7 mmol) in chloroform (10 ml), the reaction solution was cooled to -10 ° C. Subsequently, a solution obtained by diluting trifluoromethanesulfonic anhydride (0.5 g, 1.6 mmol) with 0.5 ml of chloroform was added dropwise over 2 minutes. After stirring at the same temperature for 2 hours, the reaction temperature was gradually raised to room temperature and further stirred for 10 hours. After completion of the reaction, chloroform was distilled off under reduced pressure, the residue was purified by silica gel column chromatography, and N-methyl-N- (2-trifluoromethanesulfonylaminobenzyl) -2-phenoxypropionamide (0.1 g, Yield 20%). The refractive index was 1.5281 (25 ° C.).

Example 4
Synthesis of N-methyl-N- {2- [N-trifluoromethanesulfonyl-N- (2-methylpropoxycarbonyl)] aminobenzyl} -4-chlorobenzamide (Compound No. 1-150) N-methyl-N- (2-Trifluoromethanesulfonylaminobenzyl) -4-chlorobenzamide (0.5 g, 1.2 mmol) and triethylamine (0.1 g, 1.4 mmol) were suspended in tetrahydrofuran (20 ml) and then isobutyl chlorocarbonate ( 0.2 g, 1.4 mmol) was added and stirred at room temperature for 8 hours. Ice water was then added and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated. The precipitated crystals were washed with hexane-ether, and N-methyl-N- {2- [N-trifluoromethanesulfonyl-N- (2-methylpropoxycarbonyl)] aminobenzyl} -4-chlorobenzamide (0.1 g, Yield 21%). The melting point was 97.2 ° C.

Example 5
(5-1) Synthesis of N- (2-nitrobenzyl) carbamic acid 1,1-dimethylethyl ester 2-Nitrobenzylamine (5.0 g, 32.9 mmol) was suspended in tetrahydrofuran (100 ml), and then iced. Under cooling, di-t-butyl dicarbonate (7.9 g, 36.2 mmol) was added and stirred at room temperature for 3 hours. Then, water was added and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous sodium sulfate and the solvent was distilled off, and then N- (2-nitrobenzyl) carbamic acid 1,1-dimethylethyl ester (8.3 g, yield 100%). )

(5-2) Synthesis of N- (2-aminobenzyl) carbamic acid 1,1-dimethylethyl ester N- (2-nitrobenzyl) carbamic acid 1,1-dimethylethyl ester (8.3 g, 32.9 mmol) ) And ammonium chloride (0.9 g, 16.5 mmol) were suspended in ethanol (100 ml) and water (50 ml), and then iron (9.2 g, 167.5 mmol) was added and refluxed for 1 hour. The solution was filtered through Celite, and then the solvent was distilled off. Then, water was added and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous sodium sulfate and the solvent was distilled off, and then N- (2-aminobenzyl) carbamic acid 1,1-dimethylethyl ester (5.6 g, yield 76%). )

(5-3) Synthesis of N- (2-trifluoromethanesulfonylaminobenzyl) carbamic acid 1,1-dimethylethyl ester N- (2-aminobenzyl) carbamic acid 1,1-dimethylethyl ester (2.7 g, 11 0.9 mmol) and triethylamine (1.3 g, 12.5 mmol) were suspended in chloroform (50 ml), and the solution was brought to −10 ° C. or lower with a cryogen, and then trifluoromethanesulfonic anhydride (3.4 g, 11. 9 mmol) was added dropwise. After stirring at −10 ° C. or lower for 1 hour, the reaction was stopped by adding dilute hydrochloric acid. Then, water was added and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous sodium sulfate and the solvent was distilled off. Then, N- (2-trifluoromethanesulfonylaminobenzyl) carbamic acid 1,1-dimethylethyl ester (4.5 g, 100%).

(5-4) Synthesis of N- [2- (aminomethyl) phenyl] trifluoromethanesulfonamide hydrochloride (Compound No. 8-1) N- (2-trifluoromethanesulfonylaminobenzyl) carbamic acid 1,1-dimethyl The ethyl ester was suspended in concentrated hydrochloric acid (50 ml) and ethanol (50 ml) and refluxed for 1 hour. Thereafter, the solvent was distilled off to obtain N- [2- (aminomethyl) phenyl] trifluoromethanesulfonamide hydrochloride (4.0 g, yield 100%). The melting point was 178-182 ° C.

Example 6
(6-1) Synthesis of N-methyl-N- (2-nitrobenzyl) carbamic acid 1,1-dimethylethyl ester (2-nitrobenzyl) methylamine (4.0 g, 24.1 mmol) was added to tetrahydrofuran (100 ml). Then, di-t-butyl dicarbonate (5.8 g, 26.5 mmol) was added under ice cooling, and the mixture was stirred at room temperature for 2 hours. Then, water was added and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous sodium sulfate and the solvent was distilled off. Then, N-methyl-N- (2-nitrobenzyl) carbamic acid 1,1-dimethylethyl ester (7.5 g, Yield 100%).

(6-2) Synthesis of N-methyl-N- (2-aminobenzyl) carbamic acid 1,1-dimethylethyl ester N-methyl-N- (2-nitrobenzyl) carbamic acid 1,1-dimethylethyl ester ( 7.5 g, 28.2 mmol) and ammonium chloride (0.8 g, 14.1 mmol) were suspended in ethanol (80 ml) and water (40 ml), then iron (7.9 g, 141.0 mmol) was added. And refluxed for 1 hour. The solution was filtered through Celite, and then the solvent was distilled off. Then, water was added and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous sodium sulfate and the solvent was distilled off. Then, N-methyl-N- (2-aminobenzyl) carbamic acid 1,1-dimethylethyl ester (4.4 g, Yield 66%) was obtained.

(6-3) Synthesis of N-methyl-N- (2-trifluoromethanesulfonylaminobenzyl) carbamic acid 1,1-dimethylethyl ester N-methyl-N- (2-aminobenzyl) carbamic acid 1,1-dimethyl Ethyl ester (4.4 g, 18.7 mmol) and triethylamine (2.0 g, 19.6 mmol) were suspended in chloroform (50 ml). Product (5.3 g, 18.7 mmol) was added dropwise. After stirring at −10 ° C. or lower for 1 hour, the reaction was stopped by adding dilute hydrochloric acid. Then, water was added and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated. Then, N-methyl-N- (2-trifluoromethanesulfonylaminobenzyl) carbamic acid 1,1-dimethylethyl ester (6 .3 g, 92% yield).

(6-4) Synthesis of N- [2- (aminomethyl) phenyl] -N-methyltrifluoromethanesulfonamide hydrochloride (Compound No. 8-3) N-methyl-N- (2-trifluoromethanesulfonylaminobenzyl) ) Carbamic acid 1,1-dimethylethyl ester was suspended in concentrated hydrochloric acid (50 ml) and ethanol (50 ml) and refluxed for 1 hour. Thereafter, the solvent was distilled off to obtain N- [2- (aminomethyl) phenyl] -N-methyltrifluoromethanesulfonamide hydrochloride (5.6 g, yield 100%). The melting point was 174-178 ° C.

Example 7
(7-1) Synthesis of N-methyl-N- (2-nitrobenzyl) -4-chlorobenzthioamide (Compound No. 4-64) N-methyl-N- (2-nitrobenzyl) -4-chlorobenzamide (1.0 g, 3.3 mmol) and 2,4-bis (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetan-2,4-disulfide (1.6 g, 4.0 mmol) Was dissolved and suspended in toluene (15 ml) and heated to reflux for 4 hours. After cooling to room temperature, ethyl acetate was added, and the mixture was washed with 3N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine in this order. The organic layer was concentrated and purified using silica gel column chromatography (hexane: ethyl acetate = 4: 1) to give N-methyl-N- (2-nitrobenzyl) -4-chlorobenzthioamide (0.6 g, yield). 60%). The melting point was 148-149 ° C.

(7-2) Synthesis of N- (2-aminobenzyl) -N-methyl-4-chlorobenzthioamide (Compound No. 6-62) N-methyl-N- (2-nitrobenzyl) -4-chlorobenz Thioamide (0.6 g, 2.0 mmol) and ammonium chloride (0.06 g, 1.0 mmol) were dissolved in water (5 ml) and ethanol (10 ml), and iron powder (0.6 g, 10.0 mmol) was dissolved. And heated to reflux for 2 hours. After cooling to room temperature, insolubles were removed by Celite filtration, and ethyl acetate was added to the filtrate for liquid separation operation. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain N- (2-aminobenzyl) -N-methyl-4-chlorobenzthioamide (0.45 g, yield 77%). The refractive index was 1.6149 (20 ° C.).

(7-3) Synthesis of N-methyl-N- (2-trifluoromethanesulfonylaminobenzyl) -4-chlorobenzthioamide (Compound No. 1-68) N- (2-aminobenzyl) -N-methyl-4 -Chlorobenzthioamide (0.45 g, 1.5 mmol) and triethylamine (0.24 g, 2.4 mmol) were dissolved in chloroform (7 ml), and then the reaction solution was cooled to -10 ° C. Then, trifluoromethanesulfonic anhydride (0.46 g, 1.5 mmol) was added dropwise over 20 minutes. After stirring at the same temperature for 2 hours, ice was added, 6N hydrochloric acid was added to acidify the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed once with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1) to give N-methyl-N- (2-trifluoromethanesulfonylaminobenzyl) -4-chlorobenzthioamide (0.2 g, yield 35%). Got. The melting point was 75-85 ° C.

Example 8
(8-1) Synthesis of N-methyl-N- (2-nitrobenzyl) -1-methyl-1,4,5,6-tetrahydro-3-cyclopentapyrazolecarboxamide (Compound No. 4-103) (2) -Nitrobenzyl) methylamine (0.5 g, 3.0 mmol) was dissolved in tetrahydrofuran (15 ml). Here, triethylamine (0.8 g, 7.5 mmol), 2-chloro-1-methylpyridinium iodide (0.9 g, 3.6 mmol), 1-methyl-1,4,5,6-tetrahydro-3 -Cyclopentapyrazole carboxylic acid (0.6 g, 3.3 mmol) was added and stirred at room temperature for 5 hours. Water was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give N-methyl-N- (2-nitrobenzyl) -1-methyl-1,4,5,6-tetrahydro- 3-cyclopentapyrazole carboxamide (0.9 g, yield 92%) was obtained. The melting point was 120-123 ° C.

(8-2) Synthesis of N- (2-aminobenzyl) -N-methyl-1-methyl-1,4,5,6-tetrahydro-3-cyclopentapyrazolecarboxamide (Compound No. 6-99) N- Methyl-N- (2-nitrobenzyl) -1-methyl-1,4,5,6-tetrahydro-3-cyclopentapyrazole carboxamide (0.4 g, 1.3 mmol) and ammonium chloride (0.04 g, 0 .6 mmol) was dissolved in water (5 ml) and ethanol (10 ml), iron powder (0.4 g, 6 mmol) was added, and the mixture was heated to reflux for 2 hours. After cooling to room temperature, insolubles were removed by Celite filtration, and ethyl acetate was added to the filtrate for liquid separation operation. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give N- (2-aminobenzyl) -N-methyl-1-methyl-1,4,5,6-tetrahydro-3-cyclopentapyrazole carboxamide (0. 3 g, 91% yield). The refractive index was 1.5844 (25 ° C.).

(8-3) N-methyl-N- (2-trifluoromethanesulfonylaminobenzyl) -1-methyl-1,4,5,6-tetrahydro-3-cyclopentapyrazole carboxamide (Compound No. 1-108) Synthesis N- (2-aminobenzyl) -N-methyl-1-methyl-1,4,5,6-tetrahydro-3-cyclopentapyrazole carboxamide (0.3 g, 1.1 mmol) and triethylamine (0.2 g) 1.8 mmol) was dissolved in chloroform (7 ml), and the reaction solution was cooled to -10 ° C. Then trifluoromethanesulfonic anhydride (0.3 g, 1.1 mmol) was added dropwise over 20 minutes. After stirring at the same temperature for 2 hours, ice was added, 6N hydrochloric acid was added to acidify the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed once with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1) to give N-methyl-N- (2-trifluoromethanesulfonylaminobenzyl) -1-methyl-1,4,5,6-tetrahydro-3. -Cyclopentapyrazole carboxamide (0.3 g, 61% yield) was obtained. The melting point was 99 to 101 ° C.

Example 9
Synthesis of N-methyl-N- (2-trifluoromethanesulfonylaminobenzyl) -2-nitrobenzamide (Compound No. 1-180) N- [2- (aminomethyl) phenyl] -trifluoromethanesulfonamide hydrochloride (0 .3 g, 1.0 mmol) and triethylamine (0.2 g, 2.0 mmol) were suspended in tetrahydrofuran (15 ml) and 2-nitrobenzoyl chloride (90%) (0.2 g, 1.0 mmol) was cooled with ice. ) And stirred at the same temperature for 1 hour. Then, water was added and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 1: 1), and N-methyl-N— (2-Trifluoromethanesulfonylaminobenzyl) -2-nitrobenzamide (0.3 g, yield 78%) was obtained. The melting point was 117-120 ° C.

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

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

Test Example 1 Herbicidal effect test on paddy weeds before emergence (pre) 75 cm ² plastic pot filled with soil (soil loam soil), seeded with seeds of dog firefly, paddy field weeds, 75 cm ^{3 of} soil mixed with seeds of Azena After covering with, the water was submerged to a state of 5 cm depth. On the next day, a drug containing the compounds of the present invention (compounds shown in Tables 1 and 2) prepared according to Formulation Examples 1 to 4 as active ingredients was diluted with water and treated dropwise on the water surface (effective dose) : 1 kg / ha). Then, the plants were grown in a greenhouse, and the herbicidal effect was investigated 21 days after the treatment.
Criteria for herbicidal effect (degree of growth inhibition) and phytotoxicity.
4 ... 90% to 100% herbicidal effect, phytotoxicity.
3 ... 70% -89% herbicidal effect, phytotoxicity.
2. 40% to 69% herbicidal effect, phytotoxicity.
1 ... 1% to 39% herbicidal effect, phytotoxicity.
0 ... 0% herbicidal effect, phytotoxicity.
The results are shown in Table 10. In the table, “/” indicates that the test was not performed.

Test Example 2 Herbicidal effect test on paddy weeds after emergence (post) 75 cm ² plastic pot filled with soil (soil loam soil), seeds of Inobie and Inuta firefly which are paddy field weeds, and soil mixed with Azena seeds After covering with 75 cm ³ , the soil was submerged to a depth of 5 cm and grown in a greenhouse. When the test plant was in the first leaf stage, a drug containing the compound of the present invention (compounds shown in Tables 1 and 2) as an active ingredient was diluted with water and dropped onto the water surface (effective dose: 1 kg / kg). ha). Then, the plants were grown in a greenhouse, and the herbicidal effect was investigated 21 days after the treatment. The results are shown in Table 10.

Test 3 Phylogenetic test on transplanted rice paddy 75 cm ² plastic pot filled with soil (soil loam soil), submerged to a depth of 5 cm, and transplanted 2 rice plants (variety: Nipponbare) at a transplant depth of 1 cm did. Growing in a greenhouse, 5 days after transplantation, a drug containing the compound of the present invention (compounds listed in Tables 1 and 2) as an active ingredient was diluted with water and dropped onto the water surface (effective dose: 1 kg) / Ha). Subsequently, it was grown in a greenhouse, and the phytotoxicity was investigated 21 days after the treatment. The results are shown in Table 10.

Claims (7)

Formula (I)

{Wherein R ¹ represents a halo (C ₁ -C ₆ ) alkyl group. R ² represents a hydrogen atom, a (C ₁ -C ₆ ) alkyl group, a (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group, a phenyl (C ₁ -C ₆ ) alkyl group, or the same or different Well, a substituted phenyl (C ₁ -C ₆ ) alkyl group having 1 to 5 substituents selected from Y (Y is shown below) on the ring, (C ₁ -C ₆ ) alkylcarbonyl group, ₁ to 5 selected from halo (C ₁ -C ₆ ) alkylcarbonyl group, (C ₂ -C ₆ ) alkenylcarbonyl group, phenylcarbonyl group, which may be the same or different, and Y (Y is shown below) Substituted phenylcarbonyl group, heterocyclic carbonyl group (heterocycle is pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, oxathiin ring, dihydrooxathiin ring, furan ring, tetrahydrofuran ring, thiophene ring, tetrahydrothiophene Ring, tetra Dropyran ring, tetrahydrothiopyran ring, oxazole ring, oxazoline ring, isoxazole ring, isoxazoline ring, oxadiazole ring, thiazole ring, thiazoline ring, isothiazole ring, thiadiazole ring, imidazole ring, imidazoline ring, triazole ring, triazoline ring, A pyrazole ring, a pyrazoline ring, a pyrrole ring or a pyrrolidine ring.), Which may be the same or different, and a substituted heterocyclic carbonyl group having 1 to 5 substituents selected from Y (Y is shown below) (The heterocycle is the same as above.), (C ₁ -C ₆ ) alkoxycarbonyl group, halo (C ₁ -C ₆ ) alkoxycarbonyl group, phenoxycarbonyl group, the same or different, Y (Y is described later) A substituted phenoxycarbonyl group having 1 to 5 substituents selected from: (C ₁ -C ₆ ) alkylthiocarbonyl group, (C ₁ -C ₆ ) alkylsulfonyl group, halo (C ₁ -C ₆ ) alkylsulfonyl group, phenylsulfonyl group may be the same or different, and Y (Y is shown below). ) Substituted phenylsulfonyl group having 1 to 5 substituents selected from: (C ₁ -C ₆ ) alkylthio (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkylthio (C _1- C ₆ ) alkyl group, phenylthio (C ₁ -C ₆ ) alkyl group, which may be the same or different, and a substituent having 1 to 5 substituents selected from Y (Y is shown below) on the ring Phenylthio (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkylsulfinyl (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkylsulfinyl (C ₁ -C ₆ ) alkyl group, phenylsulfinyl (C ₁ -C ₆₎ alkyl groups, the same or different and, Y (Y It is shown in the following. 1-5 substituted phenylsulfanyl having a substituent on the ring nyl (C ₁ -C ₆₎ alkyl group selected from), (C ₁ -C ₆₎ alkylsulfonyl (C ₁ -C ₆₎ alkyl group, halo (C ₁ -C ₆ ) alkylsulfonyl (C ₁ -C ₆ ) alkyl group, phenylsulfonyl (C ₁ -C ₆ ) alkyl group, which may be the same or different and selected from Y (Y is shown below). A substituted phenylsulfonyl (C ₁ -C ₆ ) alkyl group having 1 to 5 substituents on the ring.
R ³ and R ⁴ may be the same or different, and are a hydrogen atom, a (C ₁ -C ₆ ) alkyl group, a (C ₃ -C ₆ ) cycloalkyl group, a (C ₁ -C ₆ ) alkoxy group, a halogen atom or A cyano group is shown. R ³ and R ⁴ can be bonded to each other to form a ^3- to 7-membered ring.
R ⁵ is a hydrogen atom, (C ₁ -C ₆ ) alkyl group, (C ₃ -C ₆ ) cycloalkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkyl group, phenyl ( C ₁ -C ₆ ) alkyl group, which may be the same or different, and substituted phenyl (C ₁ -C ₆ ) having 1 to 5 substituents selected from Y (Y is shown below) on the ring An alkyl group, a phenyl group, which may be the same or different, and a substituted phenyl group having 1 to 5 substituents selected from Y (Y will be described later) and a heterocyclic group (the heterocyclic ring is the same as above. ), Which may be the same or different, and a substituted heterocyclic group having one or more substituents selected from Y (Y is shown below) (the heterocyclic ring is the same as above), (C ₁ -C ₆ ) alkoxycarbonyl (C ₁ -C ₆₎ alkyl group, phenoxycarbonyl (C ₁ -C ₆₎ alkyl groups, the same or different and, Y (Y is described below Shown.) Substituted phenoxycarbonyl (C ₁ -C ₆₎ alkyl group having from 1 to 5 substituents selected on the ring from, mono (C ₁ -C ₆₎ alkylaminocarbonyl (C ₁ -C ₆₎ alkyl group, the same or different and may di (C ₁ -C ₆₎ alkylaminocarbonyl (C ₁ -C ₆₎ alkyl group, phenyl aminocarbonyl (C ₁ -C ₆₎ alkyl groups, the same or different and, A substituted phenylaminocarbonyl (C ₁ -C ₆ ) alkyl group having 1 to 5 substituents selected from Y (Y is shown below) on the ring, phenyl (C ₁ -C ₆ ) alkylaminocarbonyl A substituted phenyl (C ₁ -C ₆₎ having 1 to 5 substituents selected from (C ₁ -C ₆ ) alkyl group or the same or different, Y (Y is shown below) on the ring ) Represents an alkylaminocarbonyl (C ₁ -C ₆ ) alkyl group.
R ⁶ and R ⁷ may be the same or different and are a hydrogen atom, a (C ₁ -C ₆ ) alkyl group, a (C ₃ -C ₆ ) cycloalkyl group, a (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆₎ alkoxycarbonyl group, a halogen atom or a cyano group. R ⁶ and R ⁷ can be bonded to each other to form a 3- to 7-membered ring.
A represents an oxygen atom or a sulfur atom.
G is an oxygen atom, a sulfur atom, —C (R ⁸ ) (R ⁹ ) — (wherein R ⁸ and R ⁹ may be the same or different, a hydrogen atom, a (C ₁ -C ₆ ) alkyl group, ( C ₃ -C ₆ ) cycloalkyl group, (C ₁ -C ₆ ) alkoxy group, halogen atom or cyano group, and R ⁸ and R ⁹ may be bonded to each other to form a 3- to 7-membered ring. And can be combined with R ⁶ or R ⁷ to form a 4- to 7-membered ring.), A carbonyl group, a group represented by —C (═CH ₂ ) —, or —C (═NOR ^10. )-(Wherein R ¹⁰ may be a hydrogen atom, a (C ₁ -C ₆ ) alkyl group, a phenyl (C ₁ -C ₆ ) alkyl group, or the same or different, and Y (Y is shown below). A substituted phenyl (C ₁ -C ₆ ) alkyl group having 1 to 5 selected substituents on the ring).
Q may be a (C ₁ -C ₆ ) alkyl group, a halo (C ₁ -C ₆ ) alkyl group, a (C ₃ -C ₆ ) cycloalkyl group, and may be the same or different, and Y (Y is shown below). (C ₃ -C ₆ ) cycloalkyl group, cyano group, amino group, (C ₁ -C ₆ ) alkoxycarbonyl group, (C ₁ -C ₆ ) alkoxycarbonylamino group having one or more substituents selected from The phenylcarbonylamino group may be the same or different, and the substituted phenylcarbonylamino group having 1 to 5 substituents selected from Y (Y will be described later), the phenyl group may be the same or different. , Y (Y is shown below), a substituted phenyl group having 1 to 5 substituents, a heterocyclic group (the heterocyclic ring is the same as above), or the same or different, Y (Y Is a substituent having one or more substituents selected from: Heterocyclic group (heterocyclic ring are the same. Above) shows a.
a and b may be the same or different and represent 0 or 1;
X may be the same or different and is a hydrogen atom, halogen atom, (C ₁ -C ₆ ) alkyl group, (C ₂ -C ₆ ) alkenyl group, (C ₂ -C ₆ ) alkynyl group, cyclo (C _3- C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, cyclohalo (C ₃ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, ( C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylthio (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkylthio (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkylsulfinyl groups, halo (C ₁ -C ₆₎ alkylsulfinyl group, (C ₁ -C ₆₎ alkylsulfonyl groups, halo (C ₁ -C ₆₎ alkylsulfonyl group, a phenyl group, the same or different In addition, a substituted phenyl group having 1 to 5 substituents selected from Y (Y is shown below), a phenoxy group, may be the same or different, and is selected from Y (Y is shown below). A substituted phenoxy group having 1 to 5 substituents, a phenylthio group, which may be the same or different, and a substituted phenylthio group having 1 to 5 substituents selected from Y (Y is shown below), A phenylsulfinyl group, which may be the same or different, a substituted phenylsulfinyl group having 1 to 5 substituents selected from Y (Y will be described later), a phenylsulfonyl group, which may be the same or different; A substituted phenylsulfonyl group having 1 to 5 substituents selected from (Y is shown below), (C ₁ -C ₆ ) alkylcarbonyl group, halo (C ₁ -C ₆ ) alkylcarbonyl group, phenyl Cal Group, which may be identical or different, Y (Y is shown later.) Substituted phenylcarbonyl group having 1 to 5 substituents selected from, (C ₁ -C ₆₎ alkoxycarbonyl group, a carboxyl group Mono (C ₁ -C ₆ ) alkylaminocarbonyl group, which may be the same or different, di (C ₁ -C ₆ ) alkylaminocarbonyl group, phenylaminocarbonyl group, which may be the same or different, and Y (Y is described later) Shown in ) A substituted phenylaminocarbonyl group having 1 to 5 substituents selected from the above, a phenyl (C ₁ -C ₆ ) alkylaminocarbonyl group, which may be the same or different, and Y (Y is shown below) 1 to 4 selected from a substituted phenyl (C ₁ -C ₆ ) alkylaminocarbonyl group, hydroxyl group, amino group, cyano group or nitro group having 1 to 5 substituents selected from The substituent of is shown.
Y may be the same or different and is a halogen atom, (C ₁ -C ₆ ) alkyl group, (C ₂ -C ₆ ) alkenyl group, (C ₂ -C ₆ ) alkynyl group, cyclo (C ₃ -C ₆ ) Alkyl, halo (C ₁ -C ₆ ) alkyl, cyclohalo (C ₃ -C ₆ ) alkyl, (C ₁ -C ₆ ) alkoxy, halo (C ₁ -C ₆ ) alkoxy, (C _1- C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group, halo (C ₁ -C ₆ ) alkylsulfinyl group, (C ₁ -C ₆ ) alkylsulfonyl group Halo (C ₁ -C ₆ ) alkylsulfonyl group, phenyl group, which may be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, (C ₂ -C ₆ ) alkenyl group, (C _2- C ₆ ) alkynyl group, cyclo (C ₃ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, cyclohalo (C ₃ -C ₆ ) alkyl group, (C ₁ -C ₆ ) al Coxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group, halo (C ₁ -C ₆ ) alkylsulfinyl group, (C ₁ -C ₆ ) alkylsulfonyl group, halo (C ₁ -C ₆ ) alkylsulfonyl group, (C ₁ -C ₆ ) alkylcarbonyl group, halo (C ₁ -C ₆ ) Alkylcarbonyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, carboxyl group, mono (C ₁ -C ₆ ) alkylaminocarbonyl group, di (C ₁ -C ₆ ) alkylaminocarbonyl group which may be the same or different, A substituted phenyl group having 1 to 5 substituents selected from a hydroxyl group, an amino group, a cyano group or a nitro group, a heterocyclic group (the heterocyclic group is the same as above), the same or different, and a halogen atom , (C ₁ -C ₆₎ alkyl group, (C ₂ -C ₆₎ alkenyl group (C ₂ -C ₆₎ alkynyl group, a cycloalkyl (C ₃ -C ₆₎ alkyl group, halo (C ₁ -C ₆₎ alkyl group, Shikuroharo (C ₃ -C ₆₎ alkyl group, (C ₁ -C ₆₎ Alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group, halo (C ₁ -C ₆ ) alkylsulfinyl group, (C ₁ -C ₆ ) alkylsulfonyl group, halo (C ₁ -C ₆ ) alkylsulfonyl group, (C ₁ -C ₆ ) alkylcarbonyl group, halo (C ₁ -C ₆ ) Alkylcarbonyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, carboxyl group, mono (C ₁ -C ₆ ) alkylaminocarbonyl group, di (C ₁ -C ₆ ) alkylaminocarbonyl group which may be the same or different, Substituted heterocycle having one or more substituents selected from a hydroxyl group, an amino group, a cyano group, or a nitro group (Heterocyclic group have the same meanings), a phenoxy group, which may be identical or different, halogen atom, (C ₁ -C ₆₎ alkyl group, (C ₂ -C ₆₎ alkenyl, (C ₂ -C ₆₎ Alkynyl, cyclo (C ₃ -C ₆ ) alkyl, halo (C ₁ -C ₆ ) alkyl, cyclohalo (C ₃ -C ₆ ) alkyl, (C ₁ -C ₆ ) alkoxy, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group, halo (C ₁ -C ₆ ) alkylsulfinyl group , (C ₁ -C ₆ ) alkylsulfonyl group, halo (C ₁ -C ₆ ) alkylsulfonyl group, (C ₁ -C ₆ ) alkylcarbonyl group, halo (C ₁ -C ₆ ) alkylcarbonyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, carboxyl group, mono (C ₁ -C ₆ ) alkylaminocarbonyl group, the same or different di (C ₁ -C ₆ ) alkylaminocarbonyl group, hydroxyl group, amino group, cyano group, substituted phenoxy group having 1 to 5 substituents selected from a nitro group, phenylthio group, which may be the same or different, halogen Atoms, (C ₁ -C ₆ ) alkyl groups, (C ₂ -C ₆ ) alkenyl groups, (C ₂ -C ₆ ) alkynyl groups, cyclo (C ₃ -C ₆ ) alkyl groups, halo (C ₁ -C ₆₎ ) Alkyl group, cyclohalo (C ₃ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group, halo (C ₁ -C ₆ ) alkylsulfinyl group, (C ₁ -C ₆ ) alkylsulfonyl group, halo (C ₁ -C ₆ ) alkyl sulfonyl group, (C ₁ -C ₆₎ alkylcarbonyl group, halo (C ₁ -C ₆₎ alkylcarbonyl group, (C ₁ -C ₆ Alkoxycarbonyl group, a carboxyl group, a mono (C ₁ -C ₆₎ alkylaminocarbonyl group, the same or different and may di (C ₁ -C ₆₎ alkylaminocarbonyl group, a hydroxyl group, an amino group, a cyano group or a nitro group A substituted phenylthio group having 1 to 5 substituents selected, a phenylsulfinyl group, which may be the same or different, a halogen atom, a (C ₁ -C ₆ ) alkyl group, a (C ₂ -C ₆ ) alkenyl group, (C ₂ -C ₆ ) alkynyl group, cyclo (C ₃ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, cyclohalo (C ₃ -C ₆ ) alkyl group, (C ₁ -C ₆ ) Alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group, halo (C ₁ -C ₆₎ alkylsulfinyl group, (C ₁ -C ₆₎ alkyl sulfonyl Groups, halo (C ₁ -C ₆₎ alkylsulfonyl groups, (C ₁ -C ₆₎ alkylcarbonyl group, halo (C ₁ -C ₆₎ alkylcarbonyl group, (C ₁ -C ₆₎ alkoxycarbonyl group, a carboxyl group ₁ to 5 selected from mono (C ₁ -C ₆ ) alkylaminocarbonyl group, di (C ₁ -C ₆ ) alkylaminocarbonyl group which may be the same or different, hydroxyl group, amino group, cyano group or nitro group Substituted phenylsulfinyl groups, phenylsulfonyl groups, which may be the same or different, halogen atoms, (C ₁ -C ₆ ) alkyl groups, (C ₂ -C ₆ ) alkenyl groups, (C ₂ -C ₆₎ alkynyl, cyclo (C ₃ -C ₆₎ alkyl group, halo (C ₁ -C ₆₎ alkyl group, Shikuroharo (C ₃ -C ₆₎ alkyl group, (C ₁ -C ₆₎ alkoxy groups, halo ( C ₁ -C ₆₎ alkoxy groups, (C ₁ -C ₆₎ alkylthio group, a halo C ₁ -C ₆₎ alkylthio groups, (C ₁ -C ₆₎ alkylsulfinyl groups, halo (C ₁ -C ₆₎ alkylsulfinyl group, (C ₁ -C ₆₎ alkylsulfonyl groups, halo (C ₁ -C ₆ ) Alkylsulfonyl group, (C ₁ -C ₆ ) alkylcarbonyl group, halo (C ₁ -C ₆ ) alkylcarbonyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, carboxyl group, mono (C ₁ -C ₆ ) Alkylaminocarbonyl group, optionally substituted or di (C ₁ -C ₆ ) alkylaminocarbonyl group, substituted phenylsulfonyl having 1 to 5 substituents selected from hydroxyl group, amino group, cyano group or nitro group Group, (C ₁ -C ₆ ) alkylcarbonyl group, halo (C ₁ -C ₆ ) alkylcarbonyl group, phenylcarbonyl group, which may be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, ( C ₂ -C ₆ ) alkenyl group, (C ₂ -C ₆ ) alkynyl group, cyclo (C ₃ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, cyclohalo (C ₃ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group , Halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group, halo (C ₁ -C ₆₎ alkylsulfinyl group, (C ₁ -C ₆₎ alkylsulfonyl groups, halo (C ₁ -C ₆₎ alkylsulfonyl groups, (C ₁ -C ₆₎ alkylcarbonyl group, halo (C ₁ -C ₆₎ alkylcarbonyl Group, (C ₁ -C ₆ ) alkoxycarbonyl group, carboxyl group, mono (C ₁ -C ₆ ) alkylaminocarbonyl group, di (C ₁ -C ₆ ) alkylaminocarbonyl group which may be the same or different, hydroxyl group, A substituted phenyl group having 1 to 5 substituents selected from an amino group, a cyano group or a nitro group Rubonyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, carboxyl group, mono (C ₁ -C ₆ ) alkylaminocarbonyl group, di (C ₁ -C ₆ ) alkylaminocarbonyl group which may be the same or different, phenyl Aminocarbonyl group, which may be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, (C ₂ -C ₆ ) alkenyl group, (C ₂ -C ₆ ) alkynyl group, cyclo (C ₃ -C ₆₎ alkyl group, halo (C ₁ -C ₆₎ alkyl group, Shikuroharo (C ₃ -C ₆₎ alkyl group, (C ₁ -C ₆₎ alkoxy groups, halo (C ₁ -C ₆₎ alkoxy groups, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group, halo (C ₁ -C ₆ ) alkylsulfinyl group, (C ₁ -C ₆ ) alkyl sulfonyl group, halo (C ₁ -C ₆₎ alkylsulfonyl groups, (C ₁ -C ₆₎ alkylcarbonyl group Halo (C ₁ -C ₆₎ alkylcarbonyl group, (C
₁ -C ₆₎ alkoxycarbonyl group, a carboxyl group, a mono (C ₁ -C ₆₎ alkylaminocarbonyl group, the same or different and may di (C ₁ -C ₆₎ alkylaminocarbonyl group, a hydroxyl group, an amino group, a cyano A substituted phenylaminocarbonyl group having 1 to 5 substituents selected from a group or a nitro group on the ring, a phenyl (C ₁ -C ₆ ) alkylaminocarbonyl group, the same or different, a halogen atom, ( C ₁ -C ₆ ) alkyl group, (C ₂ -C ₆ ) alkenyl group, (C ₂ -C ₆ ) alkynyl group, cyclo (C ₃ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group , Cyclohalo (C ₃ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio groups, (C ₁ -C ₆₎ alkylsulfinyl groups, halo (C ₁ -C ₆₎ alkyl Rusulfinyl group, (C ₁ -C ₆ ) alkylsulfonyl group, halo (C ₁ -C ₆ ) alkylsulfonyl group, (C ₁ -C ₆ ) alkylcarbonyl group, halo (C ₁ -C ₆ ) alkylcarbonyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, carboxyl group, mono (C ₁ -C ₆ ) alkylaminocarbonyl group, di (C ₁ -C ₆ ) alkylaminocarbonyl group, hydroxyl group, amino group which may be the same or different , A substituted phenyl (C ₁ -C ₆ ) alkylaminocarbonyl group having 1 to 5 substituents selected from a cyano group or a nitro group on the ring, a hydroxyl group, an amino group, a cyano group or a nitro group 1 to 5 substituents, and Y, together with adjacent carbon atoms or nitrogen atoms on the benzene ring or heterocyclic ring, may be the same or different, and may be the same or different, oxygen atom, sulfur atom or nitrogen atom (the nitrogen atom) Atom is hydrogen source , (C ₁ -C ₆₎ alkyl group, (C ₂ -C ₆₎ alkenyl group, may be substituted by a (C ₂ -C ₆₎ alkynyl group or a cyclo (C ₃ -C ₆₎ alkyl group.) A (C ₁ -C ₄ ) alkylene group, a halo (C ₁ -C ₄ ) alkylene group, a (C ₂ -C ₄ ) alkenylene group or a halo ( ₁ ) which may be interrupted by one or two heteroatoms selected from C ₂ -C ₄ ) Alkenylene group may form a 5- or 6-membered ring. } The haloalkyl sulfonanilide derivative represented by these, or its salt. R ¹ , R ² , R ⁵ , R ⁶ , R ⁷ , A, G, Q, a and b are the same as in claim 1, R ³ and R ⁴ represent a hydrogen atom, and X may be the same or different. Well, hydrogen atom, halogen atom, (C ₁ -C ₆ ) alkyl group, cyclo (C ₃ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, Halo (C ₁ -C ₆ ) alkoxy groups, (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl groups, halo (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl groups, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylthio (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkylthio (C _1- C ₆ ) alkyl group, (C ₁ -C ₆ ) alkylsulfinyl group, halo (C ₁ -C ₆ ) alkylsulfinyl group, (C ₁ -C ₆ ) alkylsulfonyl group, halo (C ₁ -C ₆ ) alkylsulfonyl Group, hydroxyl group, Amino group, haloalkyl sulfonanilide derivative or a salt thereof according to claim 1, wherein indicating 1-4 substituents selected from cyano group or a nitro group. R ² , R ⁵ , R ⁶ , R ⁷ , A, Q, a and b are the same as in claim 1, R ¹ represents a fluoro (C ₁ -C ₆ ) alkyl group, and R ³ and R ⁴ represent hydrogen. Represents an atom, G represents an oxygen atom or CR ⁸ R ⁹ (wherein R ⁸ and R ⁹ are the same as in claim 1);
X may be the same or different, and ₁ to 4 selected from a hydrogen atom, a halogen atom, a (C ₁ -C ₆ ) alkyl group or a (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group The substituents of
Y may be the same or different, and may be a halogen atom, a (C ₁ -C ₆ ) alkyl group, a halo (C ₁ -C ₆ ) alkyl group, a (C ₁ -C ₆ ) alkoxy group, or a halo (C ₁ -C _6). ) Alkoxy, (C ₁ -C ₆ ) alkylthio, halo (C ₁ -C ₆ ) alkylthio, (C ₁ -C ₆ ) alkylsulfinyl, halo (C ₁ -C ₆ ) alkylsulfinyl, (C ₁ -C ₆ ) alkylsulfonyl group, halo (C ₁ -C ₆ ) alkylsulfonyl group, phenyl group, which may be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) a substituted phenyl group having 1 to 5 substituents selected from an alkyl group, a (C ₁ -C ₆ ) alkoxy group, a halo (C ₁ -C ₆ ) alkoxy group, a cyano group or a nitro group, a heterocyclic ring Group (heterocyclic group is the same as in claim 1), which may be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, B (C ₃ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, cyclohalo (C ₃ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) Alkoxy, (C ₁ -C ₆ ) alkylthio, halo (C ₁ -C ₆ ) alkylthio, (C ₁ -C ₆ ) alkylsulfinyl, halo (C ₁ -C ₆ ) alkylsulfinyl, (C ₁ -C ₆ ) alkylsulfonyl group, halo (C ₁ -C ₆ ) alkylsulfonyl group, (C ₁ -C ₆ ) alkylcarbonyl group, halo (C ₁ -C ₆ ) alkylcarbonyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, a carboxyl group, a mono (C ₁ -C ₆₎ alkylaminocarbonyl group, the same or different and may di (C ₁ -C ₆₎ alkylaminocarbonyl group, a hydroxyl group, an amino group, a cyano group or a nitro group A substituted heterocyclic group having one or more substituents selected from the above (the heterocyclic group is the same as described above), Enoxy groups, which may be the same or different, are halogen atoms, (C ₁ -C ₆ ) alkyl groups, halo (C ₁ -C ₆ ) alkyl groups, (C ₁ -C ₆ ) alkoxy groups, halo (C ₁ -C ₆ ) a substituted phenoxy group having 1 to 5 substituents selected from an alkoxy group, a cyano group or a nitro group, a phenylthio group, which may be the same or different, a halogen atom, a (C ₁ -C ₆ ) alkyl group, ₁ to 5 substituents selected from a halo (C ₁ -C ₆ ) alkyl group, a (C ₁ -C ₆ ) alkoxy group, a halo (C ₁ -C ₆ ) alkoxy group, a cyano group or a nitro group Substituted phenylthio group, phenylsulfinyl group, which may be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo ₁ to 5 positions selected from (C ₁ -C ₆ ) alkoxy group, cyano group or nitro group A substituted phenylsulfinyl group having a substituent, a phenylsulfonyl group, which may be the same or different, a halogen atom, a (C ₁ -C ₆ ) alkyl group, a halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆₎ ) An alkoxy group, a halo (C ₁ -C ₆ ) alkoxy group, a substituted phenylsulfonyl group having 1 to 5 substituents selected from a cyano group or a nitro group, (C ₁ -C ₆ ) alkylcarbonyl group, halo (C ₁ -C ₆ ) alkylcarbonyl group, phenylcarbonyl group, which may be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, (C _1- C ₆ ) an alkoxy group, a halo (C ₁ -C ₆ ) alkoxy group, a substituted phenylcarbonyl group having 1 to 5 substituents selected from a cyano group or a nitro group, (C ₁ -C ₆ ) alkoxycarbonyl group , a carboxyl group, a mono (C ₁ -C ₆₎ alkyl Aminocarbonyl group, the same or different and may di (C ₁ -C ₆₎ alkylaminocarbonyl group, a phenylaminocarbonyl group, which may be identical or different, halogen atom, (C ₁ -C ₆₎ alkyl group, halo ( ₁ to 5 substituents selected from a C ₁ -C ₆ ) alkyl group, a (C ₁ -C ₆ ) alkoxy group, a halo (C ₁ -C ₆ ) alkoxy group, a cyano group or a nitro group on the ring Substituted phenylaminocarbonyl group, phenyl (C ₁ -C ₆ ) alkylaminocarbonyl group, which may be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group , (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, substituted phenyl having 1 to 5 substituents selected from cyano group or nitro group on the ring (C ₁ -C ₆₎ alkylaminocarbonyl group, or a cyano group or a nitro group 1 to 5 selected substituents, and Y, together with adjacent carbon atoms or nitrogen atoms on the benzene ring or heterocyclic ring, may be the same or different, oxygen atom, sulfur atom or nitrogen atom (The nitrogen atom is replaced by a hydrogen atom, a (C ₁ -C ₆ ) alkyl group, a (C ₂ -C ₆ ) alkenyl group, a (C ₂ -C ₆ ) alkynyl group or a cyclo (C ₃ -C ₆ ) alkyl group. May have been. The haloalkylsulfonanilide derivative according to claim 1, which may form a 5- or 6-membered ring by a (C ₁ -C ₄ ) alkylene group which may be interrupted by 1 or 2 heteroatoms selected from salts.   A herbicide comprising the haloalkylsulfonanilide derivative or a salt thereof according to any one of claims 1 to 3 as an active ingredient.   A method for using a herbicide, which comprises treating an effective amount of the herbicide according to claim 4 on soil or plants. Formula (II)

{Wherein R ¹ represents a halo (C ₁ -C ₆ ) alkyl group. R ³ and R ⁴ may be the same or different, and are a hydrogen atom, a (C ₁ -C ₆ ) alkyl group, a (C ₃ -C ₆ ) cycloalkyl group, a (C ₁ -C ₆ ) alkoxy group, a halogen atom or A cyano group is shown. R ³ and R ⁴ can be bonded to each other to form a ^3- to 7-membered ring.
R ⁵ ′ is a hydrogen atom, (C ₁ -C ₆ ) alkyl group, (C ₃ -C ₆ ) cycloalkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkyl group, phenyl (C ₁ -C ₆ ) alkyl group, which may be the same or different, substituted phenyl having 1 to 5 substituents selected from Y ′ (Y ′ is shown below) on the ring (C ₁ − C ₆ ) an alkyl group, a phenyl group, which may be the same or different, a substituted phenyl group having 1 to 5 substituents selected from Y ′ (Y ′ is shown below), a heterocyclic group (heterocycle) The groups are pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyrazinyl group, triazinyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, tetrahydrothiopyranyl group, oxazolyl group, isoxazolyl group Group, oxadiazolyl group, thi A zolyl group, an isothiazolyl group, a thiadiazolyl group, an imidazolyl group, a triazolyl group, a pyrazolyl group or a pyrrolidinyl group), which may be the same or different, and Y ′ (Y ′ is shown below). A substituted heterocyclic group having a substituent (the heterocyclic group is the same as described above), a (C ₁ -C ₆ ) alkoxycarbonyl (C ₁ -C ₆ ) alkyl group, a phenoxycarbonyl (C ₁ -C ₆ ) alkyl group, A substituted phenoxycarbonyl (C ₁ -C ₆ ) alkyl group having 1 to 5 substituents selected from Y ′ (Y ′ is shown below) on the ring, mono (C ₁ -C ₆ ) alkylaminocarbonyl (C ₁ -C ₆ ) alkyl groups, di (C ₁ -C ₆ ) alkylaminocarbonyl (C ₁ -C ₆ ) alkyl groups, which may be the same or different, phenylaminocarbonyl (C ₁ -C ₆₎ alkyl group, the same May be different, Y '(Y' is shown later.) 1-5 substituents substituted phenylaminocarbonyl having on the ring (C ₁ -C ₆₎ alkyl group selected from phenyl (C ₁ -C ₆ ) alkylaminocarbonyl (C ₁ -C ₆ ) alkyl group, which may be the same or different, and is substituted with 1 to 5 substituents selected from Y ′ (Y ′ is shown below) And substituted phenyl (C ₁ -C ₆ ) alkylaminocarbonyl (C ₁ -C ₆ ) alkyl groups.
X ′ may be the same or different and is selected from a hydrogen atom, a halogen atom, a (C ₁ -C ₆ ) alkyl group or a (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group. Of substituents.
Y ′ may be the same or different, and is a halogen atom, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group, halo (C ₁ -C ₆ ) alkylsulfinyl group, ( C ₁ -C ₆ ) alkylsulfonyl group, halo (C ₁ -C ₆ ) alkylsulfonyl group, phenyl group, which may be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, halo (C _1- C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, substituted phenyl group having 1 to 5 substituents selected from cyano group or nitro group, ring group (heterocyclic group is as defined above.) may be the same or different, a halogen atom, (C ₁ -C ₆₎ alkyl group, a cycloalkyl C ₃ -C ₆₎ alkyl group, halo (C ₁ -C ₆₎ alkyl group, Shikuroharo (C ₃ -C ₆₎ alkyl group, (C ₁ -C ₆₎ alkoxy groups, halo (C ₁ -C ₆₎ alkoxy Group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, (C ₁ -C ₆ ) alkylsulfinyl group, halo (C ₁ -C ₆ ) alkylsulfinyl group, (C _1- C ₆ ) alkylsulfonyl group, halo (C ₁ -C ₆ ) alkylsulfonyl group, (C ₁ -C ₆ ) alkylcarbonyl group, halo (C ₁ -C ₆ ) alkylcarbonyl group, (C ₁ -C ₆ ) alkoxy carbonyl group, a carboxyl group selection, mono (C ₁ -C ₆₎ alkylaminocarbonyl group, the same or different and may di (C ₁ -C ₆₎ alkylaminocarbonyl group, a hydroxyl group, an amino group, a cyano group or a nitro group A substituted heterocyclic group having one or more substituents (the heterocyclic group is the same as above), Xy group, which may be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) a substituted phenoxy group having 1 to 5 substituents selected from an alkoxy group, a cyano group or a nitro group, a phenylthio group, which may be the same or different, a halogen atom, a (C ₁ -C ₆ ) alkyl group, ₁ to 5 substituents selected from a halo (C ₁ -C ₆ ) alkyl group, a (C ₁ -C ₆ ) alkoxy group, a halo (C ₁ -C ₆ ) alkoxy group, a cyano group or a nitro group Substituted phenylthio group, phenylsulfinyl group, which may be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆₎ alkoxy group, 1 to 5 substituents selected from cyano group or a nitro group Substituted phenylsulfonyl group having, phenylsulfonyl group, which may be identical or different, halogen atom, (C ₁ -C ₆₎ alkyl group, halo (C ₁ -C ₆₎ alkyl group, (C ₁ -C ₆₎ alkoxy group , A substituted phenylsulfonyl group having 1 to 5 substituents selected from a halo (C ₁ -C ₆ ) alkoxy group, a cyano group or a nitro group, a (C ₁ -C ₆ ) alkylcarbonyl group, a halo (C ₁ -C ₆ ) alkylcarbonyl group, phenylcarbonyl group, which may be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) A substituted phenylcarbonyl group having 1 to 5 substituents selected from an alkoxy group, a halo (C ₁ -C ₆ ) alkoxy group, a cyano group or a nitro group, (C ₁ -C ₆ ) alkoxycarbonyl group, carboxyl group , mono (C ₁ -C ₆₎ alkylamine Bruno carbonyl group, the same or different and may di (C ₁ -C ₆₎ alkylaminocarbonyl group, a phenylaminocarbonyl group, the same or different and a halogen atom, (C ₁ -C ₆₎ alkyl group, halo ( ₁ to 5 substituents selected from a C ₁ -C ₆ ) alkyl group, a (C ₁ -C ₆ ) alkoxy group, a halo (C ₁ -C ₆ ) alkoxy group, a cyano group or a nitro group on the ring Substituted phenylaminocarbonyl group, phenyl (C ₁ -C ₆ ) alkylaminocarbonyl group, which may be the same or different, halogen atom, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group , (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, substituted phenyl having 1 to 5 substituents selected from cyano group or nitro group on the ring (C ₁ -C ₆ ) Select from alkylaminocarbonyl group, cyano group or nitro group 1 ′ to 5 substituents represented by Y ′ together with adjacent carbon atoms or nitrogen atoms on the benzene ring or heterocyclic ring, which may be the same or different, oxygen atom, sulfur atom or nitrogen atom (The nitrogen atom is replaced by a hydrogen atom, a (C ₁ -C ₆ ) alkyl group, a (C ₂ -C ₆ ) alkenyl group, a (C ₂ -C ₆ ) alkynyl group or a cyclo (C ₃ -C ₆ ) alkyl group. May be. ) May be interrupted by 1 or 2 heteroatoms selected from (C ₁ -C ₄ ) alkylene groups to form 5- or 6-membered rings.
However, a compound in which X ′ is a hydrogen atom, R ¹ is CF ₃ , the substitution position of R ¹ SO ₂ NH is the 4-position, and R ³ , R ^4, and R ⁵ ′ are hydrogen atoms is excluded. } Or a salt thereof. R ⁵ ′ and X ′ are the same as in claim 6, R ¹ represents a fluoro (C ₁ -C ₆ ) alkyl group, and R ³ and R ⁴ represent a hydrogen atom, salts.