JPWO2007023719A1 - Pesticide mitigation agent and herbicide composition with reduced phytotoxicity - Google Patents

Abstract

Effective against 1,2 benzisothiazolin-3-one 1,1-dioxide derivative or its salt, which is very suitable for reducing phytotoxicity of cultivated plants without reducing herbicidal effect against phytotoxicity of herbicide Provided is a safener for a herbicide characterized by containing as a component. In the general formula [I] [wherein Y represents an oxygen atom or a sulfur atom, R1 represents a C1-C16 alkyl group, a C2-C6 alkenyl group, a -WQ group, or other substituent described in the specification. W represents a C1-C6 alkyl group, Q represents a phenyl group (the group may be substituted with a halogen atom or a nitro group or other substituent described in the specification), X represents a halogen atom, C1- C6 alkyl group and other substituents described in the specification, and n represents an integer of 0 to 4,] 1,2-benzoisothiazolin-3-one 1,1-dioxide derivative represented by It is a safener for herbicides, characterized by containing.

Description

  The present invention relates to a phytotoxicity reducing agent comprising a compound having an action of protecting cultivated plants from phytotoxicity of a herbicide as an active ingredient and a herbicidal composition with reduced phytotoxicity.

  Until now, the compound described in patent documents 1-3 is known about the compound which belongs to a 1, 2- benzisothiazolin-3-one 1, 1-dioxide derivative. Patent Document 1 describes a nonlinear optical material, Patent Document 2 describes a bleaching agent and a detergent, and Patent Document 3 describes a production method, but none of them describes a method for reducing herbicide phytotoxicity.

JP-A-4-305629 U.S. Pat. No. 3,928,223 German Patent Publication No. 3040633

  In general, when herbicides are used in cultivated plants, undesirable phytotoxicity occurs against shallow seedlings, immediately after transplanting, seedlings immediately after sowing, or under adverse environmental conditions such as temperature, soil, water management, etc. There is. Also, the majority of herbicides are not sufficiently selective for all cultivated plants and can cause phytotoxicity if excessive amounts are applied unintentionally or accidentally. is there. Therefore, the range of cultivated plants to which the herbicide can be applied is limited to each herbicide, or can only be used at low usage levels that do not guarantee the desired broad herbicidal effect on the cultivated plant. There may not be.

  As a result of intensive studies to solve the above problems, the present inventors have found that 1,2-benzisothiazolin-3-one 1,1-dioxide derivatives reduce the herbicidal effect against herbicide phytotoxicity. It was found that the present invention is extremely suitable for reducing the phytotoxicity of cultivated plants, and the present invention has been completed.

That is, the present invention
(1) General formula [I]

［式中、Ｙは、酸素原子又は硫黄原子を示し、
Ｒ^１は、Ｃ_１−Ｃ_１６アルキル基、Ｃ_２−Ｃ_６アルケニル基、Ｃ_２−Ｃ_６アルキニル基、Ｃ_３−Ｃ_６シクロアルキル基、Ｃ_１−Ｃ_１０ハロアルキル基、Ｃ_１−Ｃ_６シアノアルキル基、Ｃ_３−Ｃ_６シクロアルキルＣ_１−Ｃ_６アルキル基、Ｃ_１−Ｃ_６アルコキシＣ_１−Ｃ_６アルキル基、Ｃ_１−Ｃ_６アルキルチオＣ_１−Ｃ_６アルキル基、フェニル基（該基は、ハロゲン原子、ニトロ基、Ｃ_１−Ｃ_６アルキル基、Ｃ_１−Ｃ_６アルコキシ基、Ｃ_１−Ｃ_６アルキ
ルチオ基、Ｃ_１−Ｃ_６アルコキシカルボニル基で置換されてもよい。）、−Ｗ−Ｑ基、−Ｑ^１基又は−Ｗ−Ｑ^１基を示し、
Ｗは、Ｃ_１−Ｃ_６アルキル基を示し、
Ｑは、フェニル基（該基は、ハロゲン原子、ニトロ基、シアノ基、Ｃ_１−Ｃ_６アルキル基、Ｃ_１−Ｃ_６アルコキシ基、Ｃ_１−Ｃ_６ハロアルキル基、Ｃ_１−Ｃ_６ハロアルコキシ基又は−ＮＲ^２Ｒ^３基で置換されてもよい。）を示し、
Ｑ^１は、同一若しくは相異なってよい酸素原子、硫黄原子及び窒素原子から選択される１個以上のヘテロ原子を有する炭素数３乃至１０の複素環基（該基は、ハロゲン原子、ニトロ基、シアノ基、Ｃ_１−Ｃ_６アルキル基、Ｃ_１−Ｃ_６アルコキシ基、Ｃ_１−Ｃ_６ハロアルキル基、Ｃ_１−Ｃ_６ハロアルコキシ基又は−ＮＲ^２Ｒ^３基で置換されてもよい。）を示し、Ｘは、ハロゲン原子、ニトロ基、シアノ基、Ｃ_１−Ｃ_６アルキル基、Ｃ_１−Ｃ_６アルコキシ基、Ｃ_１−Ｃ_６ハロアルキル基、Ｃ_１−Ｃ_６ハロアルコキシ基又は−ＮＲ^２Ｒ^３基を示し、
Ｒ^２及びＲ^３は、それぞれ独立に水素原子、Ｃ_１−Ｃ_６アルキル基、Ｃ_２−Ｃ_６アルケニル基又はフェニル基（該基は、ハロゲン原子、ニトロ基、シアノ基、Ｃ_１−Ｃ_６アルキル基、Ｃ_１−Ｃ_６アルコキシ基、Ｃ_１−Ｃ_６ハロアルキル基、Ｃ_１−Ｃ_６ハロアルコキシ基又は−ＮＲ^４Ｒ^５基で置換されてもよい。）を示し、
Ｒ^４及びＲ^５は、それぞれ独立に水素原子又はＣ_１−Ｃ_６アルキル基を示し、
ｎは、０から４の整数を示す。］
で表される１，２−ベンゾイソチアゾリン−３−オン １，１−ジオキシド誘導体又はその塩を有効成分として含有することを特徴とする除草剤の薬害軽減剤。

[Wherein Y represents an oxygen atom or a sulfur atom,
R ¹ is a C ₁ -C ₁₆ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₁₀ haloalkyl group, or a C ₁ -C _6. cyanoalkyl _group, C 3 -C ₆ cycloalkyl _C 1 -C ₆ alkyl _group, C 1 -C ₆ alkoxy _C 1 -C ₆ alkyl _group, C 1 -C ₆ alkylthio _C 1 -C ₆ alkyl group, a phenyl group ( The group may be substituted with a halogen atom, a nitro group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ alkylthio group, or a C ₁ -C ₆ alkoxycarbonyl group. , -WQ group, -Q ¹ group or -W-Q ¹ group,
W _represents a C 1 -C ₆ alkyl group,
Q is phenyl (in which the group, a halogen atom, a nitro group, a cyano _group, C 1 -C _{6 alkyl,} C 1 -C ₆ alkoxy _group, C 1 -C ₆ haloalkyl _group, C 1 -C ₆ haloalkoxy Group may be substituted with a group or a —NR ² R ³ group),
Q ¹ represents a heterocyclic group having 3 to 10 carbon atoms having one or more hetero atoms selected from the same or different oxygen, sulfur and nitrogen atoms (the group is a halogen atom, a nitro group, (It may be substituted with a cyano group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ haloalkoxy group or a —NR ² R ³ group.) are shown, X is a halogen atom, a nitro group, a cyano _group, C 1 -C _{6 alkyl,} C 1 -C ₆ alkoxy _group, C 1 -C ₆ haloalkyl _group, C 1 -C ₆ haloalkoxy group or -NR ² R represents a group ³
R ² and R ³ are each independently a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group or a phenyl group (the group is a halogen atom, a nitro group, a cyano group, C ₁ -C _6). An alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ haloalkoxy group or a —NR ⁴ R ⁵ group, which may be substituted).
R ⁴ and R ⁵ each independently represent a hydrogen atom or a C ₁ -C ₆ alkyl group,
n represents an integer of 0 to 4. ]
A herbicide safener comprising a 1,2-benzisothiazolin-3-one 1,1-dioxide derivative represented by the formula: or a salt thereof as an active ingredient.

(2) In the general formula [I],
Y is an oxygen atom,
R ¹ is a C ₁ -C ₁₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, a phenyl group (the group is a halogen atom, a nitro group, a C _1- A C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ alkylthio group, a C ₁ -C ₆ alkoxycarbonyl group), a -WQ group, a -Q ¹ group or- a ^{W-Q 1} group,
W is _C 1 -C ₆ alkyl group,
Q is a phenyl group (the group is a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ haloalkoxy group) Or may be substituted with a —NR ² R ³ group).
Q ¹ is a heterocyclic group having 3 to 10 carbon atoms having one or more heteroatoms selected from oxygen, sulfur and nitrogen atoms which may be the same or different (the group is a halogen atom, a nitro group, a cyano group, Group, C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ haloalkoxy group or —NR ² R ³ group may be substituted). Show
X is a halogen atom, a nitro group, a cyano _group, C 1 -C _{6 alkyl,} C 1 -C ₆ alkoxy _group, C 1 -C ₆ haloalkyl _group, C 1 -C ₆ haloalkoxy group or a ^-NR 2 ^{R 3} group And
R ² and R ³ are each independently a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group or a phenyl group (the group is a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group) Group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ haloalkoxy group or a —NR ⁴ R ⁵ group).
R ⁴ and R ⁵ are each independently a hydrogen atom or a C ₁ -C ₆ alkyl group,
n is an integer from 0 to 4,
The herbicide safener according to (1) above.

(3) In the general formula [I],
Y is an oxygen atom,
R ¹ is a C ₁ -C ₁₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy C
₁ -C ₆ alkyl group, -W-Q group, a -Q ¹ group or ^{-W-Q 1} group W is _C 1 -C ₃ alkyl group,
Q is a phenyl group (the group is a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group or a C ₁ -C ₆ haloalkoxy group) And may be substituted with
Q ¹ is a heterocyclic group having 3 to 6 carbon atoms having one or more heteroatoms selected from oxygen atom, sulfur atom and nitrogen atom which may be the same or different (the group is a halogen atom, nitro group, cyano group Group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group or a C ₁ -C ₆ haloalkoxy group).
X is a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group or a C ₁ -C ₆ haloalkoxy group,
n is an integer from 0 to 4,
The herbicide safener according to (1) above.

(4) In the general formula [I],
Y is an oxygen atom,
R ¹ is a C ₁ -C ₁₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, a -WQ group or a -WQ ¹ group,
W is _C 1 -C ₃ alkyl group,
Q is a phenyl group (the group is a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group or a C ₁ -C ₆ haloalkoxy group) And may be substituted with
Q ¹ is a heterocyclic group having 3 to 6 carbon atoms having one or more heteroatoms selected from oxygen atom, sulfur atom and nitrogen atom which may be the same or different (the group is a halogen atom, nitro group, cyano group Group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group or a C ₁ -C ₆ haloalkoxy group).
n is 0,
The herbicide safener according to (1) above.

(5) In the general formula [I],
Y is an oxygen atom,
R ¹ is a C ₁ -C ₁₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group or a -WQ group,
W is _C 1 -C ₃ alkyl group,
Q is a phenyl group (the group is a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group or a C ₁ -C ₆ haloalkoxy group) And may be substituted with
n is 0,
The herbicide safener according to (1) above.

(6) In the general formula [I],
Y is an oxygen atom,
R ¹ is a C ₁ -C ₁₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group or a -WQ group,
W is _C 1 -C ₂ alkyl group,
Q is phenyl (in which the group, a halogen atom, a nitro group, a cyano _group, C 1 -C _{6 alkyl,} C 1 -C ₆ alkoxy group) may be substituted with. ) And
n is 0,
The herbicide safener according to (1) above.

(7) In the general formula [I],
Y is an oxygen atom,
R ¹ is a C ₁ -C ₁₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group or a -WQ ¹ group,
W is _C 1 -C ₂ alkyl group,
Q ¹ represents a pyridyl group (the group may be substituted with a halogen atom);
n is 0,
The herbicide safener according to (1) above.

｛式中、ｎは０から２の整数を表し、ｍは１から３の整数を表し、Ｒ^５及びＲ^６は互いに独立して、水素原子、シアノ基、アルコキシカルボニル基、Ｃ_１−Ｃ_６アルキル基、ハロゲン原子又はＣ_１−Ｃ_６ハロアルキル基を表し、
Ｒ^１及びＲ^２は、水素原子、［Ｃ_３−Ｃ_８シクロアルキル基、Ｃ_１−Ｃ_６アルコキシ基、Ｃ_１−Ｃ_６アルキルカルボニル基、Ｃ_１−Ｃ_６アルキルチオ基、Ｃ_１−Ｃ_６アルキルスルフィニル基、Ｃ_１−Ｃ_６アルキルスルホニル基、Ｃ_１−Ｃ_６アルキルアミノ基、ジ（Ｃ_１−Ｃ_６アルキル）アミノ基、水酸基、シアノ基、Ｃ_１−Ｃ_６アルコキシカルボニル基、Ｃ_１−Ｃ_６アルキルアミノカルボニル基、ジ（Ｃ_１−Ｃ_６アルキル）アミノカルボニル基、（Ｃ_１−Ｃ_６アルキルチオ）カルボニル基、カルボキシル基、（置換されていてもよい）ベンジルオキシ基、（置換されていてもよい）フェノキシ基若しくは（置換されていてもよい）フェニル基で置換されていてもよい］Ｃ_１−Ｃ_８アルキル基、Ｃ_３−Ｃ_８シクロアルキル基、Ｃ_１−Ｃ_６アルコキシカルボニル基、Ｃ_１−Ｃ_６アルキルアミノカルボニル基、ジ（Ｃ_１−Ｃ_６アルキル）アミノカルボニル基、Ｃ_１−Ｃ_６アルキルチオカルボニル基、カルボキシル基又は置換されていてもよいフェニル基を表し、或いはＲ^１及びＲ^２はこれらの結合した炭素原子と共にＣ_３−Ｃ_７のスピロ環を形成してもよく、
Ｒ^３及びＲ^４は、水素原子、（同一若しくは相異なる１から３個のハロゲン原子、Ｃ_３−Ｃ_８シクロアルキル基又はＣ_１−Ｃ_６アルコキシ基で置換されていてもよい）Ｃ_１−Ｃ_８アルキル基又はＣ_３−Ｃ_８シクロアルキル基を表し、Ｒ^３及びＲ^４はこれらの結合した炭素原子と共にＣ_３−Ｃ_７のスピロ環を形成してもよく、或いはＲ^１、Ｒ^２、Ｒ^３及びＲ^４はこれらの結合した炭素原子と共に５から８員環を形成してもよく、
Ｙは、水素原子、Ｃ_１−Ｃ_６アルコキシカルボニル基、カルボキシル基、Ｃ_２−Ｃ_６アルケニル基、［同一若しくは相異なる１から３個のハロゲン原子、Ｃ_１−Ｃ_６アルコキシ基、Ｃ_２−Ｃ_６アルケニルオキシ基、Ｃ_２−Ｃ_６アルキニルオキシ基、（置換されていてもよい）ベンジルオキシ基、Ｃ_１−Ｃ_６アルコキシカルボニル基、カルボキシル基、水酸基又はホルミル基で置換されていてもよい］Ｃ_１−Ｃ_１０アルキル基或いは（１から５個の同一若しくは相異なるＲ^７で置換された）フェニル基を表し、
Ｒ^７は、水素原子、［同一若しくは相異なる１から３個のハロゲン原子、Ｃ_１−Ｃ_６アルコキシ基、水酸基、Ｃ_１−Ｃ_６アルキルチオ基、Ｃ_１−Ｃ_６アルキルスルフィニル基、Ｃ_１−Ｃ_６アルキルスルホニル基、Ｃ_１−Ｃ_６アルキルアミノ基、ジ（Ｃ_１−Ｃ_６）アルキルアミノ基、シアノ基又は（置換されていてもよい）フェノキシで置換されていてもよい］Ｃ_１−Ｃ_６アルキル基、（同一若しくは相異なる１から３個のハロゲン原子、Ｃ_１−Ｃ_６アルコキシ基、Ｃ_２−Ｃ_６アルケニル基、Ｃ_２−Ｃ_６アルキニル基、Ｃ_１−Ｃ_６アルコキシカルボニル基、Ｃ_１−Ｃ_６アルキルカルボニル基又はＣ_３−Ｃ_８シクロアルキル基で置換されていてもよい）Ｃ_１−Ｃ_６アルコキシ基、Ｃ_２−Ｃ_６アルケニル基、Ｃ_３−Ｃ_８シクロアルキルオキシ基、（同一若しくは相異なる１から３個のハロゲン原子又はＣ_１−Ｃ_６アルコキシ基で置換されていてもよい）Ｃ_１−Ｃ_６アルキルチオ基、（同一若しくは相異なる１から３個のハロゲン原子又はＣ_１−Ｃ_６アルコキシ基で置換されていてもよい）Ｃ_１−Ｃ_６アルキルスルフィニル基、（同一若しくは相異なる１から３個のハロゲン原子又はＣ_１−Ｃ_６アルコキシ基で置換されていてもよい）Ｃ_１−Ｃ_６アルキルスルホニル基、（置換されていてもよい）ベンジルオキシ基、（Ｃ_１−Ｃ_６アルキル基、Ｃ_１−Ｃ_６アルキルスルホニル基、Ｃ_１−Ｃ_６アルキルカルボニル（Ｃ_１−Ｃ_６アルキル）基又はＣ_１−Ｃ_６アルキルスルホニル（Ｃ_１−Ｃ_６アルキル）基で置換されていてもよい）アミノ基、ジ（Ｃ_１−Ｃ_６アルキル）アミノ基、ハロゲン原子、シアノ基、ニトロ基、Ｃ_１−Ｃ_６アルコキシカルボニル基、Ｃ_３−Ｃ_８シクロアルキルオキシカルボニル基、カルボキシル基、Ｃ_２−Ｃ_６アルケニルオキシカルボニル基、Ｃ_２−Ｃ_６アルキニルオキシカルボニル基、（置換されていてもよい）ベンジルオキシカルボニル基、（置換されていてもよい）フェノキシカルボニル基或いはＣ_１−Ｃ_６アルキルカルボニルオキシ基を表す。｝
及び一般式［ＩＩＩ］を有するイソオキサゾリン誘導体又はその薬理上許容される塩：

｛式中、Ｒ^１及びＲ^２は、同一又は異なって、水素原子、Ｃ_１−Ｃ_１０アルキル基、Ｃ_３−Ｃ_８シクロアルキル基又はＣ_３−Ｃ_８シクロアルキルＣ_１−Ｃ_３アルキル基を示すか、或いはＲ¹とＲ²とが一緒になって、これらの結合した炭素原子と共にＣ_３−Ｃ_７のスピロ環を示し、
Ｒ^３及びＲ^４は、同一又は異なって、水素原子、Ｃ_１−Ｃ_１０アルキル基又はＣ_３−Ｃ_８シクロアルキル基を示すか、或いはＲ^３とＲ^４とが一緒になって、これらの結合した炭素原子と共にＣ_３−Ｃ_７のスピロ環を示し、さらにＲ^１、Ｒ^２、Ｒ^３及びＲ^４はこれらの結合した炭素原子と共に５から８員環を形成することもでき、
Ｒ^５及びＲ^６は、同一又は相異なって、水素原子、ハロゲン原子、Ｃ_１−Ｃ_１０アルキル基又はＣ_１−Ｃ_６ハロアルキル基を示し、
Ｙは窒素原子、酸素原子及び硫黄原子より選択される任意のヘテロ原子を有する５から６員の芳香族ヘテロ環基又は芳香族ヘテロ縮合環基を示し、これらのヘテロ環基は置換基群αより選択される、０から６個の同一又は相異なる基で置換されていてもよく、又、隣接したアルキル基同士、アルコキシ基同士、アルキル基とアルコキシ基、アルキル基とアルキルチオ基、アルキル基とアルキルスルホニル基、アルキル基とモノアルキルアミノ基又はアルキル基とジアルキルアミノ基が２個結合して１から４個のハロゲン原子で置換されてもよい５から８員環を形成されていてもよく、又、これらのヘテロ環基のヘテロ原子が窒素原子の時は酸化されてＮ−オキシドになってもよく、
ｎは０から２の整数を示す。｝
「置換基群α」
水酸基、チオール基、ハロゲン原子、Ｃ_１−Ｃ_１０アルキル基、置換基群βより選択される任意の基でモノ置換されたＣ_１−Ｃ_１０アルキル基、Ｃ_１−Ｃ_４ハロアルキル基、Ｃ_３−Ｃ_８シクロアルキル基、Ｃ_１−Ｃ_１０アルコキシ基、置換基群γより選択される任意の基でモノ置換されたＣ_１−Ｃ_１０アルコキシ基、Ｃ_１−Ｃ_４ハロアルコキシ基、Ｃ_３−Ｃ_８シクロアルキルオキシ基、Ｃ_３−Ｃ_８シクロアルキルＣ_１−Ｃ_３アルキルオキシ基、Ｃ_１−Ｃ_１０アルキルチオ基、置換基群γより選択される任意の基でモノ置換されたＣ_１−Ｃ_１０アルキルチオ基、Ｃ_１−Ｃ_４ハロアルキルチオ基、Ｃ_２−Ｃ_６アルケニル基、Ｃ_２−Ｃ_６アルケニルオキシ基、Ｃ_２−Ｃ_６アルキニル基、Ｃ_２−Ｃ_６アルキニルオキシ基、Ｃ_１−Ｃ_１０アルキルスルフィニル基、置換基群γより選択される任意の基でモノ置換されたＣ_１−Ｃ_１０アルキルスルフィニル基、Ｃ_１−Ｃ_１０アルキルスルホニル基、置換基群γより選択される任意の基でモノ置換されたＣ_１−Ｃ_１０アルキルスルホニル基、Ｃ_１−Ｃ_４ハロアルキルスルフィニル基、置換基群γより選択される任意の基でモノ置換されたＣ_１−Ｃ_１０アルキルスルホニルオキシ基、Ｃ_１−Ｃ_４ハロアルキルスルホニル基、Ｃ_１−Ｃ_１０アルキルスルホニルオキシ基、Ｃ_１−Ｃ_４ハロアルキルスルホニルオキシ基、置換されていてもよいフェニル基、置換されていてもよいフェノキシ基、置換されていてもよいフェニルチオ基、置換されていてもよい芳香族ヘテロ環基、置換されていてもよい芳香族ヘテロ環オキシ基、置換されていてもよい芳香族ヘテロ環チオ基、置換されていてもよいフェニルスルフィニル基、置換されていてもよいフェニルスルホニル基、置換されていてもよい芳香族ヘテロ環スルホニル基、置換されていてもよいフェニルスルホニルオキシ基、アシル基、Ｃ_１−Ｃ_４ハロアルキルカルボニル基、置換されていてもよいベンジルカルボニル基、置換されていてもよいベンゾイル基、カルボキシル基、Ｃ_１−Ｃ_１０アルコキシカルボニル基、置換されていてもよいベンジルオキシカルボニル基、置換されていてもよいフェノキシカルボニル基、シアノ基、カルバモイル基（該基の窒素原子は同一又は異なって、Ｃ_１−Ｃ_１０アルキル基又は置換されていてもよいフェニル基で置換されていてもよい。）、Ｃ_１−Ｃ_６アシルオキシ基、Ｃ_１−Ｃ_４ハロアルキルカルボニルオキシ基、置換されていてもよいベンジルカルボニルオキシ基、置換されていてもよいベンゾイルオキシ基、ニトロ基、アミノ基（該基の窒素原子は同一又は異なって、Ｃ_１−Ｃ_１０アルキル基、置換されていてもよいフェニル基、Ｃ_１−Ｃ_６アシル基、Ｃ_１−Ｃ_４ハロアルキルカルボニル基、置換されていてもよいベンジルカルボニル基、置換されていてもよいベンゾイル基、Ｃ_１−Ｃ_１０アルキルスルホニル基、Ｃ_１−Ｃ_４ハロアルキルスルホニル基、置換されていてもよいベンジルスルホニル基又は置換されていてもよいフェニルスルホニル基で置換されていてもよい。）
「置換基群β」
水酸基、Ｃ_３−Ｃ_８シクロアルキル基（該基はハロゲン原子又はアルキル基で置換されてもよい）、Ｃ_１−Ｃ_１０アルコキシ基、Ｃ_１−Ｃ_１０アルキルチオ基、Ｃ_１−Ｃ_１０アルキルスルホニル基、Ｃ_１−Ｃ_１０アルコキシカルボニル基、Ｃ_２−Ｃ_６ハロアルケニル基、アミノ基（該基の窒素原子は同一又は異なって、Ｃ_１−Ｃ_１０アルキル基、Ｃ_１−Ｃ_６アシル基、Ｃ_１−Ｃ_４ハロアルキルカルボニル基、Ｃ_１−Ｃ_１０アルキルスルホニル基、Ｃ_１−Ｃ_４ハロアルキルスルホニル基で置換されていてもよい）、カルバモイル基（該基の窒素原子は同一又は異なって、Ｃ_１−Ｃ_１０アルキル基で置換されていてもよい）、Ｃ_１−Ｃ_６アシル基、Ｃ_１−Ｃ_４ハロアルキルカルボニル基、Ｃ_１−Ｃ_１０アルコキシイミノ基、シアノ基、置換されていてもよいフェニル基、置換されていてもよいフェノキシ基
「置換基群γ」
Ｃ_１−Ｃ_１０アルコキシカルボニル基、置換されていてもよいフェニル基、置換されていてもよい芳香族ヘテロ環基、シアノ基、カルバモイル基（該基の窒素原子は同一又は異なって、Ｃ_１−Ｃ_１０アルキル基で置換されていてもよい。）
よりなる群から選ばれる少なくとも１種の除草活性化合物
とを含有することを特徴とする薬害軽減された除草剤組成物。(8) (A) 1,2-benzisothiazolin-3-one 1,1-dioxide derivative represented by the general formula [I] according to any one of (1) to (7) or a salt thereof;
(B) Pyrimisulphane, benzobicyclone, oxadichromephone, sulfonylurea compound, triazolopyrimidine compound, pyrimidinyloxy (thio) benzoic acid compound, triketone compound, chloroacetamide compound, oxazolidinedione compound, triazole Compound, thiocarbamate compound, tetrazolinone compound, isoxazoline derivative having the general formula [II] or a pharmacologically acceptable salt thereof:

{Wherein n represents an integer of 0 to 2, m represents an integer of 1 to 3, and R ⁵ and R ⁶ are independently of each other a hydrogen atom, a cyano group, an alkoxycarbonyl group, C ₁ -C ₆ It represents an alkyl group, a halogen atom or a _C 1 -C ₆ haloalkyl group,
R ¹ and R ² are each a hydrogen atom, a [C ₃ -C ₈ cycloalkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ alkylcarbonyl group, a C ₁ -C ₆ alkylthio group, a C ₁ -C ₆ alkylsulfinyl _group, C 1 -C ₆ alkylsulfonyl _group, C 1 -C ₆ alkylamino group, di _(C 1 -C ₆ alkyl) amino group, a hydroxyl group, a cyano _group, C 1 -C ₆ alkoxycarbonyl group, _{C 1} -C ₆ alkylaminocarbonyl group, di (C ₁ -C ₆ alkyl) aminocarbonyl group, (C ₁ -C ₆ alkylthio) carbonyl group, carboxyl group, (optionally substituted) benzyloxy group, (substituted) may be) phenoxy group or (optionally substituted by substituted may be) phenyl] C ₁ -C ₈ alkyl group, C ₃ -C ₈ consequent Alkyl _group, C 1 -C ₆ alkoxycarbonyl _group, C 1 -C ₆ alkylamino group, di _(C 1 -C ₆ alkyl) aminocarbonyl _group, C 1 -C ₆ alkyl thiocarbonyl group, is a carboxyl group or a substituted Or R ¹ and R ² together with these bonded carbon atoms may form a C ₃ -C ₇ spiro ring,
R ³ and ^{R 4} are hydrogen atoms, (the same or different 1 to 3 halogen _atoms, C 3 -C ₈ optionally substituted cycloalkyl group or a _C 1 -C ₆ alkoxy group) _{C 1} - C ₈ alkyl or _C 3 -C ₈ cycloalkyl, ^{R 3} and ^{R 4} may form a spiro ring of _C 3 -C ₇ with these bonded carbon atoms, or ^R 1, ^{R 2} , R ³ and R ⁴ together with these bonded carbon atoms may form a 5- to 8-membered ring,
Y is a hydrogen atom, a C ₁ -C ₆ alkoxycarbonyl group, a carboxyl group, a C ₂ -C ₆ alkenyl group, [1 to 3 halogen atoms that are the same or different, a C ₁ -C ₆ alkoxy group, a C _2- A C ₆ alkenyloxy group, a C ₂ -C ₆ alkynyloxy group, a benzyloxy group (which may be substituted), a C ₁ -C ₆ alkoxycarbonyl group, a carboxyl group, a hydroxyl group or a formyl group. A C ₁ -C ₁₀ alkyl group or a phenyl group (substituted with 1 to 5 identical or different R ⁷ ),
R ⁷ represents a hydrogen atom, [1 to 3 halogen atoms that are the same or different, a C ₁ -C ₆ alkoxy group, a hydroxyl group, a C ₁ -C ₆ alkylthio group, a C ₁ -C ₆ alkylsulfinyl group, a C _1- C ₆ alkylsulfonyl group, C ₁ -C ₆ alkylamino group, di (C ₁ -C ₆ ) alkylamino group, cyano group or (optionally substituted) may be substituted with phenoxy] C _1- C ₆ alkyl group, (1 to 3 halogen atoms which are the same or different, C ₁ -C ₆ alkoxy group, C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, C ₁ -C ₆ alkoxycarbonyl group A C ₁ -C ₆ alkylcarbonyl group or a C ₃ -C ₈ cycloalkyl group, which may be substituted with a C ₁ -C ₆ alkoxy group, a C ₂ -C ₆ alkenyl group, or a C ₃ -C ₈ cycloalkyl group, (identical or different 1 to may 3 is substituted with a halogen atom or a _C 1 -C ₆ alkoxy _group) C 1 -C ₆ alkylthio group, (identical or different 1 C ₁ -C ₆ alkylsulfinyl group (optionally substituted with 3 to 3 halogen atoms or C ₁ -C ₆ alkoxy groups), 1 to 3 halogen atoms or the same or different C ₁ -C ₆ alkoxy groups C ₁ -C ₆ alkylsulfonyl group (which may be substituted with a group), benzyloxy group (which may be substituted), (C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ alkylcarbonyl _(C 1 -C ₆ alkyl) may be substituted with a group or _C 1 -C ₆ alkylsulfonyl _(C 1 -C ₆ alkyl) group) a Mino group, di (C ₁ -C ₆ alkyl) amino group, halogen atom, cyano group, nitro group, C ₁ -C ₆ alkoxycarbonyl group, C ₃ -C ₈ cycloalkyloxycarbonyl group, carboxyl group, C _2- C ₆ alkenyloxycarbonyl group, C ₂ -C ₆ alkynyloxycarbonyl group, (optionally substituted) benzyloxycarbonyl group, (optionally substituted) phenoxycarbonyl group or C ₁ -C ₆ alkylcarbonyloxy group Represents a group. }
And an isoxazoline derivative having the general formula [III] or a pharmacologically acceptable salt thereof:

{Wherein R ¹ and R ² are the same or different and are a hydrogen atom, a C ₁ -C ₁₀ alkyl group, a C ₃ -C ₈ cycloalkyl group or a C ₃ -C ₈ cycloalkyl C ₁ -C ₃ alkyl group. Or R ¹ and R ² together represent a C ₃ -C ₇ spiro ring with these bonded carbon atoms,
R ³ and R ⁴ are the same or different and each represents a hydrogen atom, a C ₁ -C ₁₀ alkyl group or a C ₃ -C ₈ cycloalkyl group, or R ³ and R ⁴ are taken together, Exhibiting a C ₃ -C ₇ spiro ring with bonded carbon atoms, and R ¹ , R ² , R ³ and R ⁴ can also form a 5- to 8-membered ring with these bonded carbon atoms;
R ⁵ and R ⁶ are the same or different and each represents a hydrogen atom, a halogen atom, a C ₁ -C ₁₀ alkyl group or a C ₁ -C ₆ haloalkyl group,
Y represents a 5- to 6-membered aromatic heterocyclic group or an aromatic hetero-fused cyclic group having an arbitrary hetero atom selected from a nitrogen atom, an oxygen atom and a sulfur atom, and these heterocyclic groups are substituted with a substituent group α And may be substituted with 0 to 6 identical or different groups selected from each other, and adjacent alkyl groups, alkoxy groups, alkyl groups and alkoxy groups, alkyl groups and alkylthio groups, alkyl groups and An alkylsulfonyl group, an alkyl group and a monoalkylamino group or an alkyl group and a dialkylamino group may be bonded to form a 5- to 8-membered ring which may be substituted with 1 to 4 halogen atoms; Moreover, when the hetero atom of these heterocyclic groups is a nitrogen atom, it may be oxidized to N-oxide,
n represents an integer of 0 to 2. }
`` Substituent group α ''
A hydroxyl group, a thiol group, a halogen _atom, C 1 _{-C 10} alkyl groups, mono-substituted by any group selected from Substituent group β a _C 1 _{-C 10} alkyl _group, C 1 -C ₄ haloalkyl groups, _{C 3} -C ₈ cycloalkyl _group, C 1 _{-C 10} alkoxy group, mono-substituted by any group selected from substituent group γ the _C 1 _{-C 10} alkoxy _group, C 1 -C ₄ haloalkoxy groups, _{C 3} -C ₈ cycloalkyl _group, C 3 -C ₈ cycloalkyl _C 1 -C ₃ alkyl _group, C 1 _{-C 10} alkylthio group, _{C 1} which is mono-substituted by any group selected from substituent group γ -C ₁₀ alkylthio _group, C 1 -C ₄ haloalkylthio _group, C 2 -C ₆ alkenyl _group, C 2 -C ₆ alkenyloxy _group, C 2 -C ₆ alkynyl _group, C 2 -C ₆ Arukiniruoki _Group, C 1 _{-C 10} alkylsulfinyl group, mono-substituted by any group selected from Substituent group γ the _C 1 _{-C 10} alkylsulfinyl _group, C 1 _{-C 10} alkylsulfonyl group, from Substituent group γ C ₁ -C ₁₀ alkylsulfonyl group monosubstituted with any selected group, C ₁ -C ₄ haloalkylsulfinyl group, C ₁ -C ₁₀ monosubstituted with any group selected from substituent group γ an alkylsulfonyloxy group, C ₁ -C ₄ haloalkylsulfonyl groups, C ₁ -C ₁₀ alkyl sulfonyloxy group, C ₁ -C ₄ haloalkylsulfonyl group, an optionally substituted phenyl group, optionally substituted phenoxy Group, phenylthio group which may be substituted, aromatic heterocyclic group which may be substituted, aromatic which may be substituted Heterocyclic oxy group, optionally substituted aromatic heterocyclic thio group, optionally substituted phenylsulfinyl group, optionally substituted phenylsulfonyl group, optionally substituted aromatic heterocyclic sulfonyl group , optionally substituted phenylsulfonyloxy group, acyl groups, C ₁ -C ₄ haloalkylcarbonyl group, an optionally substituted benzylcarbonyl group, optionally substituted benzoyl group, carboxyl groups, C ₁ -C ₁₀ alkoxycarbonyl group, optionally substituted benzyloxycarbonyl group, optionally substituted phenoxycarbonyl group, cyano group, carbamoyl group (the nitrogen atom of the group is the same or different, C ₁ -C ₁₀ alkyl group Alternatively, it may be substituted with an optionally substituted phenyl group. ), C ₁ -C ₆ acyloxy group, C ₁ -C ₄ haloalkylcarbonyloxy group, optionally substituted benzylcarbonyloxy group, optionally substituted benzoyloxy group, nitro group, amino group (of the group) nitrogen atom may be the same or _different, C 1 _{-C 10} alkyl group, optionally substituted _phenyl, C 1 -C ₆ acyl _group, C 1 -C ₄ haloalkylcarbonyl group, optionally benzylcarbonyl optionally substituted group, substituted by an optionally substituted benzoyl groups, C ₁ -C ₁₀ alkyl sulfonyl group, C ₁ -C ₄ haloalkylsulfonyl groups, optionally substituted benzylsulfonyl group or an optionally substituted phenylsulfonyl group May be.)
"Substituent group β"
_Hydroxyl, C 3 -C ₈ cycloalkyl group (which may be substituted with a halogen atom or an alkyl _group), C 1 _{-C 10} alkoxy _group, C 1 _{-C 10} alkylthio _groups, C 1 _{-C 10} alkyl sulfonyl A group, a C ₁ -C ₁₀ alkoxycarbonyl group, a C ₂ -C ₆ haloalkenyl group, an amino group (the nitrogen atom of the group is the same or different, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₆ acyl group, A C ₁ -C ₄ haloalkylcarbonyl group, a C ₁ -C ₁₀ alkylsulfonyl group, which may be substituted with a C ₁ -C ₄ haloalkylsulfonyl group, a carbamoyl group (the nitrogen atom of the group is the same or different, and ₁ -C ₁₀ optionally substituted with an alkyl _group), C 1 -C ₆ acyl _group, C 1 -C ₄ haloalkylcarbonyl _group, C 1 _{-C 10} alkoxy Amino group, a cyano group, a phenyl group which may be substituted, an optionally substituted phenoxy group "substituent group γ"
C ₁ -C ₁₀ alkoxycarbonyl group, an optionally substituted phenyl group, an optionally substituted aromatic heterocyclic group, a cyano group, a nitrogen atom of the carbamoyl group (in which the same or different, C ₁ - it may be substituted with C ₁₀ alkyl group.)
A herbicide composition with reduced phytotoxicity, comprising at least one herbicidal active compound selected from the group consisting of:

(9) A sulfonylurea compound is amidesulfuron, azimusulfuron, bensulfuron methyl, chlorimuron ethyl, chlorsulfuron, synosulfuron, cyclosulfamuron, etamethsulfuron methyl, ethoxysulfuron, frazasulfuron, Flupirsulfuron, foramsulfuron, halosulfuron methyl, imazosulfuron, iodosulfuron, mesosulfuron methyl, metsulfuron methyl, nicosulfuron, oxasulfuron, primsulfuron, prosulfuron, pyrazosulfuron ethyl, rimsulfuron, sulfometuron Methyl, sulfosulfuron, thifensulfuron methyl, triasulfuron, tribenuron methyl, trifloxysulfuron, triflusulfuron methyl and trito Reduced phytotoxicity herbicidal composition according to the at least one selected from the group consisting of iodosulfuron (8).

(10) The herbicide composition with reduced phytotoxicity according to (8), wherein the triazolopyrimidine-based compound is at least one selected from the group consisting of chloranthram methyl, diclosram, flurosum ram, flumethram, methotram, and penoxsulam.

(11) The aforementioned pyrimidinyloxy (thio) benzoic acid compound is at least one selected from the group consisting of pyrithiobac, pyrithiobac sodium salt, pyriminobac-methyl, bispyribac, bispyribac sodium salt, pyribenzoxime and pyriftalide ( A herbicide composition with reduced phytotoxicity as described in 8).

で表される化合物（以下「ＡＶＨ−３０１」という）よりなる群から選ばれる少なくとも１種である前記（８）に記載の薬害軽減された除草剤組成物。(12) The triketone compound is mesotrione, sulcotrione, or a formula

The herbicide composition with reduced phytotoxicity according to the above (8), which is at least one selected from the group consisting of compounds represented by the formula (hereinafter referred to as “AVH-301”).

(13) The chloroacetamide compound is selected from the group consisting of propachlor, dimetachlor, metazachlor, tenyl chlor, alachlor, butachlor, pretilachlor, acetochlor, propisochlor, metolachlor, S-metolachlor, dimethenamide and petoxamide. The herbicide composition with reduced phytotoxicity according to (8), wherein the herbicide composition is at least one kind.

(14) The herbicide composition with reduced phytotoxicity according to (8), wherein the oxazolidinedione compound is pentoxazone.

(15) The herbicide composition with reduced phytotoxicity according to (8), wherein the triazole-based compound is caffeentrol.

(16) The thiocarbamate compound is at least one selected from the group consisting of pyributicarb, pyributibalbu, butyrate, cycloate, dimepiperate, EPTC, esprocarb, molinate, olbencarb, pebrate, prosulfocarb, thiobencarb, thiocarbazyl and triarate. The herbicidal composition with reduced phytotoxicity according to (8).

(17) The herbicide composition with reduced phytotoxicity according to (8), wherein the tetrazolinone compound is fentolazamide.

(18) The herbicidal composition according to any one of (8) to (17), further comprising a surfactant.

(19) A 1,2-benzisothiazolin-3-one 1,1-dioxide derivative represented by the general formula [I] according to any one of (1) to (7) or a salt thereof,
(A) whether it is applied simultaneously with the herbicide,
(B) A method for reducing the herbicide's phytotoxicity, wherein the herbicide is applied in proximity to the herbicide, or (c) the seed or seedling of the cultivated plant itself is treated.

(20) The method according to (19) above, wherein the cultivated plant is wheat, rye, barley, oat, rice, corn, sorghum, cotton or soybean.

(21) The method according to (19), wherein the cultivated plant is rice in paddy fields.

  The herbicide safener and herbicidal composition of the present invention, when the herbicidal active ingredient is simply applied, growth failure of cultivated plants such as wheat, rye, barley, oat, rice, corn, sorghum, cotton, soybean, etc. Even if it corresponds to the amount of herbicidal active ingredient that causes phytotoxicity symptoms such as growth suppression and yellowing, the phytotoxicity symptoms of the target crop can be reduced or prevented.

  Hereinafter, the symbols and terms described in this specification will be described.

  The halogen atom is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

The notation such as C ₁ -C ₆ indicates that the number of carbon atoms of the subsequent substituent is 1 to 6 in this case.

The C ₁ -C ₆ alkyl group means a linear or branched alkyl group having 1 to 6 carbon atoms unless otherwise specified, and examples thereof include methyl, ethyl, n-propyl, i-propyl, and n-butyl. , S-butyl, i-butyl, t-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3 -Dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2 Examples include groups such as -trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl and the like.

The C ₁ -C ₁₆ alkyl group means a linear or branched alkyl group having ₁ to 16 carbon atoms unless otherwise specified, and includes, for example, n in addition to the examples of the C ₁ -C ₆ alkyl group described above. -Heptyl, 1-methylhexyl, 5-methylhexyl, 1,1-dimethylpentyl, 2,2-dimethylpentyl, 4,4-dimethylpentyl, 1-ethylpentyl, 2-ethylpentyl, 1,1,3- Trimethylbutyl, 1,2,2-trimethylbutyl, 1,3,3-trimethylbutyl, 2,2,3-trimethylbutyl, 2,3,3-trimethylbutyl, 1-propylbutyl, 1,1,2, 2-tetramethylpropyl, n-octyl, 1-methylheptyl, 3-methylheptyl, 6-methylheptyl, 2-ethylhexyl, 5,5-dimethylhexyl, 2,4,4- Limethylpentyl, 1-ethyl-1-methylpentyl, n-nonyl, 1-methyloctyl, 2-methyloctyl, 3-methyloctyl, 7-methyloctyl, 1-ethylheptyl group, 1,1-dimethylheptyl, 6,6-dimethylheptyl, n-decyl, 1-methylnonyl, 2-methylnonyl, 6-methylnonyl, 1-ethyloctyl, 1-propylheptyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n Examples include groups such as -tridecyl, n-tetradecyl, n-pentadecyl, and n-hexadecyl.

The C ₂ -C ₆ alkenyl group means a straight or branched alkenyl group having 2 to 6 carbon atoms unless otherwise specified, and examples thereof include vinyl, 1-propenyl, i-propenyl, 2-propenyl, -Butenyl, 1-methyl-1-propenyl, 2-butenyl, 1-methyl-2-propenyl, 3-butenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, 1,3-butadienyl, 1 -Pentenyl, 1-ethyl-2-propenyl, 2-pentenyl, 1-methyl-1-butenyl, 3-pentenyl, 1-methyl-2-butenyl, 4-pentenyl, 1-methyl-3-butenyl, 3-methyl -1-butenyl, 1,2-dimethyl-2-propenyl, 1,1-dimethyl-2-propenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1,2- Methyl-1-propenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,3-pentadienyl, 1-vinyl-2-propenyl, 1-hexenyl, 1-propyl-2-propenyl, 2- Hexenyl, 1-methyl-1-pentenyl, 1-ethyl-2-butenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-4-pentenyl, 1-ethyl-3-butenyl, 1- ( i-butyl) vinyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-2-propenyl, 1- (i-propyl) -2-propenyl, 2-methyl-2-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1,3-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 3-methyl-4-pentenyl 4-methyl-4-pentenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1,5-hexadienyl, 1-vinyl- Groups such as 3-butenyl or 2,4-hexadienyl can be mentioned.

The C ₂ -C ₆ alkynyl group means a straight or branched alkynyl group having 2 to 6 carbon atoms unless otherwise specified, and includes, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 1 -Methyl-2-propynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 1-ethyl-2-propynyl, 2-pentynyl, 3-pentynyl, 1-methyl-2-butynyl, 4-pentynyl, 1-methyl -3-butynyl, 2-methyl-3-butynyl, 1-hexynyl, 1- (n-propyl) -2-propynyl, 2-hexynyl, 1-ethyl-2-butynyl, 3-hexynyl, 1-methyl-2 -Pentynyl, 1-methyl-3-pentynyl, 4-methyl-1-pentynyl, 3-methyl-1-pentynyl, 5-hexynyl, 1-ethyl-3-butynyl, 1-ethyn 1-methyl-2-propynyl, 1-(i-propyl) -2-propynyl, may be mentioned 1,1-dimethyl-2-butynyl or 2,2-dimethyl-3 group butynyl.

Unless specifically limited to the C ₃ -C ₆ cycloalkyl indicates a cycloalkyl group having 3 to 6 carbon atoms, may be mentioned for example, cyclopropyl, cyclobutyl, groups such as cyclopentyl or cyclohexyl.

The C ₁ -C ₆ haloalkyl group represents a linear or branched alkyl group having 1 to 6 carbon atoms, which is substituted with a halogen atom. For example, fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, dichloromethyl , Trifluoromethyl, trichloromethyl, chlorodifluoromethyl, bromodifluoromethyl, 2-fluoroethyl, 1-chloroethyl, 2-chloroethyl, 1-bromoethyl, 2-bromoethyl, 2,2-difluoroethyl, 1,2-dichloroethyl 2,2-dichloroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 2-bromo-2-chloroethyl 2-chloro-1,1,2,2-tetrafluoroethyl, 1-chloro- , 2,2,2-tetrafluoroethyl, 1-chloropropyl, 2-chloropropyl, 3-chloropropyl, 2-bromopropyl, 3-bromopropyl, 2-bromo-1-methylethyl, 3-iodopropyl, 2,3-dichloropropyl, 2,3-dibromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 3-bromo-3,3-difluoropropyl, 3,3-dichloro- 3-fluoropropyl, 2,2,3,3-tetrafluoropropyl, 1-bromo-3,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, 2,2,2 -Trifluoro-1-trifluoromethylethyl, heptafluoropropyl, 1,2,2,2-tetrafluoro-1-trifluoromethylethyl, 2,3- Chloro-1,1,2,3,3-pentafluoropropyl, 2-chlorobutyl, 3-chlorobutyl, 4-chlorobutyl, 2-chloro-1,1-dimethylethyl, 4-bromobutyl, 3-bromo-2-methyl Propyl, 2-bromo-1,1-dimethylethyl, 2,2-dichloro-1,1-dimethylethyl, 2-chloro-1-chloromethyl-2-methylethyl, 4,4,4-trifluorobutyl, 3,3,3-trifluoro-1-methylpropyl, 3,3,3-trifluoro-2-methylpropyl, 2,3,4-trichlorobutyl, 2,2,2-trichloro-1,1-dimethyl Ethyl, 4-chloro-4,4-difluorobutyl, 4,4-dichloro-4-fluorobutyl, 4-bromo-4,4-difluorobutyl, 2,4-dibromo-4,4-diflu Orobutyl, 3,4-dichloro-3,4,4-trifluorobutyl, 3,3-dichloro-4,4,4-trifluorobutyl, 4-bromo-3,3,4,4-tetrafluorobutyl, 4-bromo-3-chloro-3,4,4-trifluorobutyl, 2,2,3,3,4,4-hexafluorobutyl, 2,2,3,4,4,4-hexafluorobutyl, 2,2,2-trifluoro-1-methyl-1-trifluoromethylethyl, 3,3,3-trifluoro-2-trifluoromethylpropyl, 2,2,3,3,4,4,4- Heptafluorobutyl, 2,3,3,3-tetrafluoro-2-trifluoromethylpropyl, 1,1,2,2,3,3,4,4-octafluorobutyl, nonafluorobutyl, 4-chloro- 1, 1, 2, 2, 3, 3, 4, 4 Octafluorobutyl, 5-fluoropentyl, 5-chloropentyl, 5,5-difluoropentyl, 5,5-dichloropentyl, 5,5,5-trifluoropentyl, 6,6,6-trifluorohexyl group or 5 , 5,6,6,6-pentafluorohexyl, and the like.

The C ₁ -C ₁₀ haloalkyl group refers to a linear or branched alkyl group having 1 to 10 carbon atoms, which is substituted by a halogen atom. For example, the C ₁ -C ₆ haloalkyl group described above is exemplified. In addition, groups such as a perfluoroheptyl group, a perfluorooctyl group, and a perfluorononyl group can be exemplified.

The C ₁ -C ₆ alkoxy group means a (alkyl) -O— group having 1 to 6 carbon atoms in which the alkyl portion has the above-mentioned meaning, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, pentyloxy or Groups such as hexyloxy can be mentioned.

The C ₁ -C ₆ alkylthio group means an (alkyl) -S— group having 1 to 6 carbon atoms in which the alkyl portion has the above-mentioned meaning, such as methylthio, ethylthio, propylthio, isopropylthio, butylthio, pentylthio, hexylthio, etc. Can be mentioned.

The C ₁ -C ₆ cyanoalkyl group means a cyanoalkyl group having 1 to 6 carbon atoms unless otherwise specified, and examples thereof include cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropyl, 2-cyanopropyl, Examples of the group include 3-cyanopropyl, 4-cyanobutyl, 5-cyanopentyl, and 6-cyanohexyl.

C ₃ -C ₆ cycloalkyl C ₁ -C ₆ alkyl group is an alkyl group having 1 to 6 carbon atoms in which the alkyl part and the cycloalkyl part are substituted with 1 to 6 cycloalkyl having the above-mentioned meanings. Groups such as cyclopropylmethyl, cyclopentylmethyl, 2- (cyclopropyl) ethyl, 4- (cyclopentyl) butyl, cyclohexylmethyl, 1
-Groups such as -cyclohexylethyl or 2-cyclohexylethyl can be mentioned.

C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group refers to an alkyl group having 1 to 6 carbon atoms in which the alkyl part and the alkoxy part are substituted by alkoxy having 1 to 6 carbon atoms having the above-mentioned meaning, For example, groups such as methoxymethyl, ethoxymethyl, isopropoxymethyl, pentyloxymethyl, methoxyethyl or butoxyethyl can be exemplified.

The C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group is an alkyl having 1 to 6 carbon atoms substituted by an (alkyl) -S— group having 1 to 6 carbon atoms having the above-mentioned meaning. A group such as methylthiomethyl, ethylthiomethyl, isopropylthiomethyl, pentylthiomethyl, methylthioethyl, or butylthioethyl.

The C ₁ -C ₆ haloalkoxy group represents a straight or branched alkoxy group having 1 to 6 carbon atoms in which the haloalkyl moiety is substituted with the same or different halogen atoms 1 to 13 having the above-mentioned meanings. For example, groups such as chloromethoxy, difluoromethoxy, chlorodifluoromethoxy, trifluoromethoxy, or 2,2,2-trifluoroethoxy can be exemplified.

The C ₁ -C ₆ alkoxycarbonyl group means an (alkoxy)-(C═O) — group having 1 to 6 carbon atoms in which the alkoxy moiety has the above-mentioned meaning, and examples thereof include a methoxycarbonyl group, an ethoxycarbonyl group, Examples thereof include a propoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, and a hexyloxycarbonyl group.

  Examples of the C3-C10 heterocyclic group having one or more heteroatoms selected from the same or different oxygen atom, sulfur atom and nitrogen atom include furan, thiophene, pyrrole, pyrazole, imidazole, pyridine , Pyrimidine, pyrazine, pyridazine, pyrrolidine, piperidine, piperazine, morpholine, benzofuran, benzothiophene, indole, benzoxazole, benzothiazole, benzimidazole and the like.

  Next, specific examples of the present compound represented by the general formula [I] are shown in Tables 1 to 5. However, the present compound is not limited to these compounds. The compound number is referred to in the following description.

The following notations in the tables in the present specification represent the corresponding groups as follows. For example, Me represents a methyl group, Et represents an ethyl group, Pr represents an n-propyl group, Pr-i represents an isopropyl group, Bu represents an n-butyl group, and Bu-s Represents a secondary butyl group, Bu-i represents an isobutyl group, Bu-t represents a tertiary butyl group, Pn represents an n-pentyl group, Pn-c represents a cyclopentyl group, C ₆ H ₁₃ represents an n-hexyl group, C ₇ H ₁₅ represents an n-heptyl group, C ₈ H ₁₇ represents an n-octyl group, and C ₉ H ₁₉ represents an n-nonyl group. C ₁₀ H ₂₁ represents an n-decyl group, C ₁₁ H ₂₃ represents an n-undecyl group, C ₁₂ H ₂₅ represents an n-dodecyl group, and Ph represents a phenyl group. For example, Ph (4-Cl) represents a 4-chlorophenyl group.

  Although the typical manufacturing method of the compound represented by general formula [I] is illustrated below, the manufacturing method of this compound is not limited to these methods.

（式中、Ｘ、Ｙ、ｎ及びＲ^１はそれぞれ前記と同じ意味を示し、Ｍは、水素原子、ナトリウム原子又はカリウム原子等のアルカリ金属原子を示す。）<Manufacturing method>

(In the formula, X, Y, n and R ¹ each have the same meaning as described above, and M represents an alkali metal atom such as a hydrogen atom, a sodium atom or a potassium atom.)

  The compound represented by the general formula [I] is obtained by reacting the saccharin derivative represented by the general formula [IV] with the compound [V] in the presence or absence of a base, in a solvent or in the absence of a solvent. Can be manufactured.

The amount of compound [V] used in this production method may be appropriately selected from the range of 0.5 to 10 mol, preferably 1.0 to 1.2 mol, relative to 1 mol of saccharin derivative [IV]. It is.

  Examples of the base that can be used in this production method include metal carbonates such as sodium carbonate, potassium carbonate, magnesium carbonate and calcium carbonate, metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate, sodium acetate, potassium acetate and calcium acetate. Or metal carboxylates represented by metal acetates such as magnesium acetate, metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tertiary butoxide, potassium methoxide or potassium tertiary butoxide, sodium hydroxide, potassium hydroxide , Metal hydroxides such as calcium hydroxide or magnesium hydroxide, metal hydrides such as lithium hydride, sodium hydride, potassium hydride or calcium hydride, triethylamine, pyridine or diisopropyl And organic bases such as ethylamine and the like.

  What is necessary is just to select the usage-amount of a base suitably from the range of 0-10 mol with respect to 1 mol of compound [IV], Preferably it is 0-1.2 mol.

  Solvents that can be used in this production method are not particularly limited so long as they do not inhibit the progress of this reaction. For example, ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, monoglyme or diglyme, dichloroethane, chloroform, carbon tetrachloride. Or halogenated hydrocarbons such as tetrachloroethane, aromatic hydrocarbons such as benzene, chlorobenzene, nitrobenzene or toluene, amides such as N, N-dimethylformamide or N, N-dimethylacetamide, 1,3-dimethyl- It is possible to use imidazolinones such as 2-imidazolinone, sulfur compounds such as dimethyl sulfoxide, nitriles such as acetonitrile, and a mixed solvent thereof.

  What is necessary is just to select reaction temperature from the range of the boiling point range of the inert solvent used from -20 degreeC, Preferably it is good to carry out in 0-100 degreeC.

  The reaction time varies depending on the reaction temperature, reaction substrate, reaction amount and the like, but is usually 30 minutes to 48 hours.

  The compound represented by the general formula [I], which is the target of the reaction, is collected from the reaction system by a conventional method after the completion of the reaction. The obtained target product can be purified by operations such as column chromatography and recrystallization as necessary.

The compounds of the above general formula [IV] are described in Chemische Berichte, Vol. 56, page 1810 (1923); Journal of Pharmaceutical Science, Vol. 50, Vol. 672 (1961)
A method described in JP-A-49-20779 and a method similar thereto.

  The herbicide's phytotoxicity reducing agent according to the present invention comprises the 1,2-benzisothiazolin-3-one 1,1-dioxide derivative or salt thereof obtained as described above as an active ingredient. More specifically, it constitutes the agrochemical composition of the present invention together with the herbicidal active compound described in (8) above, that is, the component (B).

  Examples of the “salt” of the 1,2-benzisothiazolin-3-one 1,1-dioxide derivative include salts of alkali metals such as sodium salt and potassium salt, and salts of amines such as ammonium salt.

Most of the component (B) used in the agrochemical composition of the present invention is, for example, The Pesticide Manual 13th edition (published by British Crop Protection Council, 2004). Year],
Shibuya Index 10th Edition, 11th Edition (SHIBUYA INDEX 10th Edition, 11th Edition) [SHIBUYA INDEX Research Group, 2005, 2006], WO 00/21924, JP 2000-44546 A No. 1, WO 01/026613, JP 2002-308857 A, WO 02/06770 or WO 2006/024820.

In addition, the compound represented by the above general formula [I] can also reduce the phytotoxicity of the herbicidal active compound shown below.
(1) Alkanamide compounds: diphenamide, napropamide (2) Anilide compounds: pentanochlor, propanil, naproanilide (3) Arylaminopropionic acid compounds: Flamprop M
(4) Aryloxyalkanoic acid compound: MCPA-thioethyl
(5) Aryloxyphenoxypropionic acid compounds: clodinahop, cihalohop-butyl, diclohop-methyl, phenoxaprop-ethyl, phenoxaprop-p-ethyl, fenthiaprop-ethyl, fluazifop, fluazifop-P, haloxyhop, haloxyhop · P, metamihop, propakizahop, quizalofop ethyl, quizalofop · P · ethyl (6) benzamide compounds: isoxaben (7) benzenedicarboxylic acid compounds: chlortal dimethyl (8) benzofuran compounds: benfrecetate, etofumesate (9 ) Benzoic acid compounds: dicamba, 2,3,6-TBA
(10) benzonitrile-based compound: diclobenil (11) benzothiadiazinone-based compound: bentazone (12) benzothiazolone-based compound: benazoline (13) bipyridylium-based compound: diquat, paraquat (14) carbamate-based compound: ashram, carbetamide, chlor Profam, Profam (15) Cyclohexanedione oxime compounds: alloxidim, butroxidim, cretodim, cycloxydim, profoxydim, cetoxydim, tepraloxydim, tralcoxydim (16) dinitroaniline compounds: benfluralin, butralin, ettalfluralin, oryzalin, pendimethalin, Trifluralin, dinitramine (17) dinitrophenol compounds: dinoterb, DNOC
(18) Diphenyl ether compounds: acifluorfen, biphenox, fluoroglycophene, fomesafen, HC-252, lactofene, oxyfluorfen, acronifene (19) Glycine compounds: glyphosate, glyphosate trimesium salt (20) hydroxybenzonitrile compounds : Ioxinyl, bromoxynyl (21) imidazolinone compound imazapyr, imazametabenz, imazaquin, imazetapir, imazamemetapyr (imazapic), imazamox (22) isoxazole compound: isoxaflutol (23) isoxazolidinone compound: cromazone (24) N-phenylphthalimide compounds: sinidone ethyl, full microlac pentyl, flumioxazin (25) oxadiazo Compounds: oxadialgyl, oxadiazone (26) oxyacetamide compounds: fluphenacet, mefenacet (27) phenoxycarboxylic acid compounds: 2,4-D, 2,4-DB, chromeprop, dichloroprop, dichloroprop- P, MCPA, MCPB, mecoprop, mecoprop-P
(28) Phenylcarbamate compounds: desmedifam, phenmedifam (29) Phenylpyrazole compounds: pyraflufen-ethyl (30) phenylpyridazine compounds: pyridates (31) Phosphinic acid compounds: bialaphos, glufosinate (32) phospho Loamidate compounds: butamifos (33) phosphorodithioate compounds: benzulide (34) phthalamate compounds: napthalam (35) pyrazole compounds: benzophenap, pyrazolate (pyrazolinate), pyrazoxifene (36) pyrazolium compounds : Difenzocoat (37) Pyridazinone compound: Chloridazone, flufenpyr, norflurazon (38) Pyridine compound: Dithiopyr, thiazopyr (39) Pyridinecarboxamide Products: diflufenican, picolinaphen (40) pyridine carboxylic acid compounds: clopyralide, picloram, triclopyr, fluroxypyr (41) pyrimidinedione compounds: butaphenacyl (42) quinoline carboxylic acid compounds: quinclolac, quinmerac (43) semicarbazone compounds : Diflufenzopyr (44) sulfonylaminocarbonyltriazolinone compounds: full carbazone sodium salt, propoxycarbazone sodium salt (45) thiadiazole compound: fluthiaset methyl (46) triazine compound: amethrin, atrazine, Cyanadine, dimetamethrin, prometone, promethrin, propazine, simazine, cimethrin, terbumethone, terbutyrazine, terbutrin, trietadine (4 ) Triazinone compounds: hexazinone, metamitron, metribudine (48) Triazolinone compounds: Amicarbazone, carfentrazone ethyl, sulfentrazone (49) Uracil compounds: Bromasil, Lenacil, Turbacil (50) Urea compounds: Chlorotolulone , Dimeflon, diuron, fluometuron, isoproturon, isouron, carbbutylate, linuron, metabenzthiazuron, methbenzuron, methoxuron, monolinuron, nebulon, ciduron, tebuthiuron, benzthiazuron, cumyluron, cycloxuron, diimuron, fludaitron, flutron Etizimuron, thiazafluron, thidiazuron (51) Other compounds: Chlorfenac, Chlorf Nenprop methyl, cinmethyline, endtal, fluridone, flurochloridone, flurtamone, indanophan, pinoxaden, quinoclamin, thidiazimine, tridiphan

  These compounds are also included in The Pesticide Manual, 13th edition (published by BritishCrop Protection Council, 2004) or Shibuya Index 10th edition, 11th edition (SHIBUYA INDEX). 10th Edition, 11th Edition) [issued by SHIBUYA INDEX Research Group, 2005, 2006] or publicly known.

  The application amount of the herbicide safener according to the present invention comprising the compound represented by the general formula [I] as an active ingredient is not particularly limited, but is usually 10 to 10,000 g per hectare of farmland. , Preferably 50 to 5000 g, more preferably 100 to 3000 g.

In the composition of the present invention, the use ratio of the component (A) and the component (B) may vary appropriately depending on the type of both, the type and growth period of the target crop, the crop transplanting period, etc. (B) The mass of the component (A) is usually 0.1 to 100 with respect to the mass of the component, preferably, the mass of the component (A) is 0.2 to 100 times the amount of pyrimisulphan and benzobicyclon. 2 to 50 times the amount, 1 to 50 times the amount for oxadichromemephone, 5 to 100 times the amount for the sulfonylurea compound, 5 to 100 times the amount for the triazolopyrimidine compound, pyrimidinyloxy (thio) benzoic acid 5 to 50 times the amount of the system compound, 1 to 50 times the amount of the triketone compound, 0.5 to 10 times the amount of the chloroacetanilide compound, and 2 to 50 times the amount of the oxazolidinedione compound , 0.25 times the O carbamate compound, 2 to 50 times the amount triazole compound, selected in the range of 3 to 30 times the amount tetrazolinone compound.

  The herbicide safener and herbicidal composition of the present invention can contain additive components that are usually used in agricultural chemical formulations as necessary.

  As this additive component, a carrier such as a solid carrier or a liquid carrier, a surfactant, a binder or a tackifier, a thickener, a colorant, a spreading agent, a spreading agent, an antifreezing agent, an anti-caking agent, Examples include disintegrants and decomposition inhibitors.

  In addition, an antiseptic | preservative, a plant piece, etc. may be used for an additional component as needed, and these additional components may be used 1 type and may be used in combination of 2 or more type.

  The additive component will be described.

  Examples of the solid support include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, diatomaceous earth, and inorganic minerals such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride. Examples thereof include organic solid carriers such as salts, synthetic silicic acid, synthetic silicate, starch, cellulose and plant powder, and plastic carriers such as polyethylene, polypropylene and polyvinylidene chloride. These may be used alone or in combination of two or more.

  Examples of the liquid carrier include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin. Alcohols, polyhydric alcohol derivatives such as propylene glycol ether, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, cellosolve, dipropyl ether, tetrahydrofuran, etc. Ethers, normal paraffins, naphthenes, isoparaffins, kerosene, mineral hydrocarbons and other aliphatic hydrocarbons, benzene, toluene, Aromatic hydrocarbons such as silene, solvent naphtha and alkylnaphthalene, halogenated hydrocarbons such as dichloroethane, chloroform and carbon tetrachloride, esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate and dimethyl adipate, Lactones such as γ-butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, N-alkylpyrrolidinone, nitriles such as acetonitrile, sulfur compounds such as dimethyl sulfoxide, soybean oil, rapeseed oil, cottonseed oil, castor oil And vegetable oil, water and the like. These may be used alone or in combination of two or more.

  The surfactant is not particularly limited, but is preferably one that gels in water or exhibits swelling properties, such as sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid ester, Polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene dialkylphenyl ether, polyoxyethylene alkylphenyl ether formalin condensate, polyoxyethylene polyoxypropylene block Polymer, alkyl polyoxyethylene polypropylene block polymer ether, polyoxyethylene alkylamine, polyoxyethylene fatty acid amide Polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene diol, polyoxyalkylene-added acetylenic diol, polyoxyethylene ether type silicon, ester type silicon, fluorine-based surfactant, polyoxy Nonionic surfactants such as ethylene castor oil, polyoxyethylene hydrogenated castor oil, alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl phenyl ether sulfates, polyoxyethylene styryl phenyl ether sulfates, alkyl benzene sulfonic acids Salt, lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonate, alkyl naphthalene sulfonate, naphthalene sulphate Salt of formalin condensate of acid, salt of formalin condensate of alkylnaphthalene sulfonic acid, fatty acid salt, polycarboxylate, N-methyl-fatty acid sarcosinate, resin acid salt, polyoxyethylene alkyl ether phosphate, polyoxy Anionic surfactants such as ethylene alkylphenyl ether phosphate, laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride, alkyldimethylbenzalkco Examples thereof include cationic surfactants such as alkylamine salts such as nium chloride, and amphoteric surfactants such as amino acid type or betaine type.

  One of these surfactants may be used, or two or more thereof may be used in combination.

  Examples of binders and tackifiers include carboxymethyl cellulose and salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinyl pyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and an average molecular weight of 6000. Examples include polyethylene glycol having ˜20,000, polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, and natural phospholipids (for example, cephalic acid and lecithin).

  Examples of the thickener include xanthan gum, guar gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch derivative, water-soluble polymer such as polysaccharide, high-purity bentonite, inorganic fine powder such as white carbon, etc. Can be given.

  Examples of the colorant include inorganic pigments such as iron oxide, titanium oxide and Prussian blue, organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes.

  Examples of the spreading agent include silicon surfactant, cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compound, crosslinked polyvinylpyrrolidone, maleic acid and styrenes, methacrylic acid copolymer, polyhydric alcohol polymer, Examples thereof include half esters with dicarboxylic acid anhydrides and water-soluble salts of polystyrene sulfonic acid.

  Examples of the spreading agent include various surfactants such as sodium dialkylsulfosuccinate, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene fatty acid ester, paraffin, terpene, polyamide resin, polyacrylate, Examples thereof include polyoxyethylene, wax, polyvinyl alkyl ether, alkylphenol formalin condensate, and synthetic resin emulsion.

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

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

  Disintegrants include, for example, sodium tripolyphosphate, sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylic acid ester copolymer, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene / isobutylene / maleic anhydride Examples thereof include a copolymer and a starch / polyacrylonitrile graft copolymer.

  Examples of decomposition inhibitors include desiccants such as zeolite, quicklime, and magnesium oxide, antioxidants such as phenols, amines, sulfurs, and phosphates, and UV absorbers such as salicylic acid and benzophenone. It is done.

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

  Examples of plant pieces include sawdust, palm, corn cob, tobacco stem and the like.

  In the herbicide safener and herbicide composition of the present invention, when the additive component is contained, the content ratio is usually 5 to 95%, preferably 20 to 90% for the carrier on a mass basis. The active agent is usually selected in the range of 0.1% to 30%, preferably 0.5 to 10%, and other additives in the range of 0.1 to 30%, preferably 0.5 to 10%.

  The herbicide safener and herbicidal composition of the present invention are a solution, emulsion, wettable powder, powder, oil, granule wettable powder, flowable powder, milk suspension, granule, jumbo drug, suspoemulsion. It is used by formulating into any dosage form such as. At the time of the formulation, a mixed composition with at least one other agrochemical such as other herbicides, insecticides, fungicides, plant growth regulators, fertilizers and the like can be used.

  In addition, the herbicide safener of the present invention may be in a form in which the above-mentioned arbitrary preparation is packaged with a water-soluble film. In this way, it contributes to labor saving and its safety in application. Can be increased.

  When the herbicide safener or herbicidal composition of the present invention is used for rice, it can also be used by applying it to a seedling box before transplanting rice into Honda.

  On the other hand, the method for reducing the phytotoxicity of the herbicide according to the present invention comprises the above-described 1,2-benzisothiazolin-3-one 1,1-dioxide derivative or a salt thereof as an active ingredient. The component (A) is applied to a cultivated plant together with the herbicidal active compound described in the above (8), that is, the component (B), or this is treated. And the component (B) may be applied simultaneously or in close proximity. Here, the proximity application means that the component (A) is applied while the period from the application of the component (B) is approached before the phytotoxicity of the target crop due to the component (B) is not manifested.

  For simultaneous application, it can be applied in the form of a ready mix. For example, the pre-formulated composition of the present invention may be used, or the above component (A) and component (B) may be used separately. And can be applied in the form of an in-situ formulation that is mixed at the time of use, ie in the form of a tank mix.

  Furthermore, the method for reducing the phytotoxicity of the herbicide according to the present invention can treat seeds or seedlings of cultivated plants with the components (A) and (B).

  The method for reducing the phytotoxicity of the herbicide according to the present invention can be suitably used for wheat, rye, barley, oat, rice, corn, sorghum, cotton, soybean, etc., particularly for rice.

The method for producing the herbicide safener and herbicide composition of the present invention is not particularly limited, but the following methods are usually used.
1. A method of adding an appropriate amount of water to a mixture of all raw materials, kneading, extruding from a screen with a hole of a certain size, granulating and drying.
2. A method of dissolving or suspending the components (A) and (B) and, if necessary, a surfactant in an organic solvent and adsorbing them on a carrier.
3. Method of mixing and crushing a mixture of all raw materials with an appropriate crusher

  Hereinafter, the production method, formulation method and use of the compound represented by the general formula [I] used in the safener and the composition of the present invention will be described in detail in the following examples. There are no restrictions.

Production Example 1
Preparation of 2-heptyloxycarbonyl-1,2-benzisothiazolin-3-one 1,1-dioxide (Compound No. 2)
5.0 g (24.4 mmol) of anhydrous saccharin sodium was dissolved in acetonitrile (50 mL), and 4.8 g (27.0 mmol) of heptyl chlorocarbonate was added. The reaction solution was stirred for 4 hours under heating to reflux. After confirming the completion of the reaction, the reaction solution was cooled to room temperature, poured into water and extracted with ethyl acetate. The obtained organic layer was washed with water and dried over anhydrous magnesium sulfate. After the inorganic substance was filtered off, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 6.1 g (yield: 80%) of 2-heptyloxycarbonyl-1,2-benzisothiazolin-3-one 1,1-dioxide as a white powder.
¹ H-NMR data (CDCl ₃ / TMS δ (ppm)): 0.89 (3H, t), 1.38 (8H, m), 1.83 (2H, quint), 4.47 (2H, t), 7.94 (3H, m) , 8.17 (1H, d)

Production Example 2
Preparation of 2- (2-butynyloxycarbonyl) -1,2-benzisothiazolin-3-one 1,1-dioxide (Compound No. 17)
1.6 g (7.5 mmol) of anhydrous saccharin sodium was dissolved in acetonitrile (50 mL), and 1.0 g (7.5 mmol) of chlorocarbonate (2-butynyl) was added. The reaction solution was stirred for 6 hours under heating to reflux. After confirming the completion of the reaction, the reaction solution was cooled to room temperature, poured into water and extracted with ethyl acetate. The obtained organic layer was washed with water and dried over anhydrous magnesium sulfate. After the inorganic substance was filtered off, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography, and 0.7 g of 2- (2-butynyloxycarbonyl) -1,2-benzisothiazolin-3-one 1,1-dioxide as a white powder (melting point: 178-180 ° C.) (Yield: 33%) was obtained.
¹ H-NMR data (CDCl ₃ / TMS δ (ppm)): 1.89 (3H, s), 5.01 (2H, s), 7.95 (3H, m), 8.17 (1H, d)

Production Example 3
Preparation of 2-ethylthiocarbonyl-1,2-benzisothiazolin-3-one 1,1-dioxide (Compound No. 71)
4.0 g (20.0 mmol) of anhydrous saccharin sodium was dissolved in acetonitrile (50 mL), and 2.7 g (22.0 mmol) of ethyl chlorothiolformate was added. The reaction solution was stirred for 5 hours under heating to reflux. After confirming the completion of the reaction, the reaction solution was cooled to room temperature, poured into water and extracted with ethyl acetate. The obtained organic layer was washed with water and dried over anhydrous magnesium sulfate. After the inorganic substance was filtered off, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography, and 0.8 g of 2-ethylthiocarbonyl-1,2-benzisothiazolin-3-one 1,1-dioxide as a white powder (melting point: 217-222 ° C.) (yield: 15 %).
¹ H-NMR data (CDCl ₃ / TMS δ (ppm)): 1.41 (3H, t), 3.09 (2H, q), 7.96 (3H, m), 8.17 (1H, d)

Production Example 4
Preparation of 2- (4-chlorobenzylthiocarbonyl) -1,2-benzisothiazolin-3-one 1,1-dioxide (Compound No. 92)
2.0 g (9.7 mmol) of anhydrous saccharin sodium was dissolved in acetonitrile (50 mL), and 2.4 g (10.7 mmol) of chlorothiolformic acid (4-chlorobenzyl) was added. The reaction solution was stirred for 3 hours under heating to reflux. After confirming the completion of the reaction, the reaction solution was cooled to room temperature, poured into water and extracted with ethyl acetate. The obtained organic layer was washed with water and dried over anhydrous magnesium sulfate. After the inorganic substance was filtered off, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography, and 0.95 g of 2- (4-chlorobenzylthiocarbonyl) -1,2-benzisothiazolin-3-one 1,1-dioxide as a white powder (melting point: 193-194 ° C.) (Yield: 27%) was obtained.
¹ H-NMR data (CDCl ₃ / TMS δ (ppm)): 4.26 (2H, s), 7.32 (4H, dd), 7.95 (3H, m), 8.15 (1H, d)

Production Example 5
2- (2,6-dichloro-4-pyridylmethyloxycarbonyl) -1,2-benzisothiazolin-3-one 1,1-dioxide (Compound No. 109)
Saccharin (0.9 g, 4.9 mmol) and 2,6-dichloro-4-pyridylmethyl chloroformate (0.9 g, 3.8 mmol) were dissolved in tetrahydrofuran (10 mL), and triethylamine (0.6 g, 5.9) was dissolved. Mmol) was added dropwise at room temperature. After stirring at room temperature for 3 hours, the mixture was poured into water, and the precipitated solid was collected by filtration. The obtained solid was washed with ethyl acetate and 2- (2,6-dichloro-4-pyridylmethyloxycarbonyl) -1,2-benzisothiazoline-3-one as a white powder (melting point: 263-265 ° C.) 0.7 g (yield: 37%) of 1,1-dioxide was obtained.
¹ H-NMR data (DMSO-d ₆ δ (ppm)): 5.59 (2H, s), 7.68 (2H, s), 8.06 (1H, m), 8.08 (1H, m), 8.22 (1H, d) , 8.41 (1H, d)

  Tables 6 and 7 show the physical property values of the compounds obtained in the above Production Examples 1 to 5 and the compounds produced by the same methods as in these Production Examples. In addition, the number in a table | surface shows the number shown in Tables 1-5.

  Examples of the herbicide safener preparations according to the present invention and the results of confirming the effects are shown below. In addition, about each composition component, a part means a mass part.

Formulation Example Example 1
<Wettable powder>
Compound No. 53 (50 parts), diatomaceous earth (45 parts), sodium dinaphthylmethane disulfonate (2 parts) and sodium lignin sulfonate (3 parts) were uniformly mixed and ground to obtain a wettable powder. Moreover, it was replaced with the compound number 53 and the wettable powder was able to be obtained similarly using each of the compounds of Tables 1-5.

Example 2
<Wettable powder>
Compound No. 2 (10 parts), polyoxyethylene alkyl ether (2 parts), naphthalenesulfonic acid formalin condensate sodium salt (2 parts), diatomaceous earth (20 parts), white carbon (15 parts), clay (51 parts) A wettable powder containing Compound No. 2 was obtained by mixing and pulverizing using an impact pulverizer. Moreover, it replaced with the compound number 2 and the wettable powder was able to be obtained similarly using each of the compound of Tables 1-5.

Example 3
<Emulsion>
Compound No. 51 (30 parts), cyclohexanone (20 parts, polyoxyethylene alkylaryl ether (11 parts), calcium alkylbenzenesulfonate (4 parts) and methylnaphthalene (35 parts) were uniformly dissolved to give an emulsion. Instead of compound No. 51, an emulsion could be obtained in the same manner using each of the compounds shown in Tables 1 to 5.

Example 4
<Granule>
Compound No. 53 (24 parts), sodium salt of lauryl alcohol sulfate (2 parts), sodium lignin sulfonate (5 parts), carboxymethylcellulose (2 parts) and clay (67 parts) were uniformly mixed and ground. Water (20 parts) was added to this mixture and kneaded, processed into 14-32 mesh granules using an extrusion granulator, and dried to give granules. Moreover, it replaced with the compound number 53 and was able to obtain a granule similarly using each of the compounds of Tables 1-5.

Example 5 for confirming the effect
50 ml of a medium obtained by diluting Murashige-Skoog medium (manufactured by Wako Pure Chemical Industries, Ltd.) 4 times with water was poured into a 50 ml flask. In this medium, a pyrimylsulfur wettable powder prepared according to Example 2 (active ingredient equivalent to 0.1 ppm) and a general formula [I] prepared according to Example 1 or Example 2 are used. A wettable powder of the compound (equivalent amount of 10 ppm of active ingredient) was added. Into this medium, 2.2.1 leaves of rice (Golden style) with roots cut to 0.5 cm are inserted, and at a temperature of 25 to 30 ° C. for 14 days in a cycle of 14 hours of light conditions and 10 hours of dark conditions. Hydroponics was performed. On the 14th day from the start of the test, the length and mass of the rice foliage were measured. Each test was carried out in two consecutive systems, and the measured values were averaged. The results are shown in Table 8.

Example 6
Paddy soil (sand loam) was filled into a 1 / 10,000a Wagner pot, and the water depth was kept at 4 cm after entering water and scuffing. The next day, rice (Aichi Asahi) grown to the second leaf stage using seedling culture soil was transplanted so that the root portion was cut to a length of 0.5 cm and the depth of the base portion was 3 cm. On the day of transplantation, an amount equivalent to 240 gai / 10a of the wettable powder of the compound represented by the general formula [I] (compound number: 53) prepared according to Example 1 was sprayed on the water surface so as to be uniform in the Wagner pot. Further, 3 days after transplantation, an amount equivalent to 10 gai / 10a of bensulfuron methyl wettable powder was sprayed on the water surface so as to be uniform in the Wagner pot. The raw mass of the above-ground part and the underground part was measured 37 days after transplantation, and the results are shown in Table 9.
Bensulfuron / methyl wettable powder was prepared in the same manner using Bensulfuron / methyl instead of Compound No. 2 in Example 2.

Example 7
A 1 / 5000a Wagner pot was filled with paddy field soil (Korean soil), and the water depth was kept at 4 cm after entering water and scuffing. The next day, rice (Ginnan style) grown to the second leaf stage using the seedling culture soil was transplanted so that the root portion was cut to a length of 0.5 cm and the depth of the base portion was 3 cm. On the next day after transplantation, a wettable powder equivalent to 240 gai / 10a of the compound represented by the general formula [I] (compound number: 53) prepared according to Example 1 was sprayed on the water surface uniformly in the Wagner pot. Further, 5 days after transplantation, an amount equivalent to 20 gai / 10a of benzobicyclone wettable powder was sprayed on the water surface so as to be uniform in the Wagner pot. 32 days after transplantation, the degree of inhibition of rice growth was examined in comparison with the control group and the untreated group, and the results are shown in Table 10.
The benzobicyclon wettable powder was prepared in the same manner using benzobicyclone instead of compound No. 2 in Example 2.

Example 8
A 1 / 5000a Wagner pot was filled with paddy field soil (Korean soil), and the water depth was kept at 4 cm after entering water and scuffing. The next day, rice (Ginnan style) grown to the second leaf stage using the seedling culture soil was transplanted so that the root portion was cut to a length of 0.5 cm and the depth of the base portion was 3 cm. On the next day after transplantation, a wettable powder 120gai / 10a equivalent amount of the compound represented by the general formula [I] (compound No. 51) prepared according to Example 1 was sprayed on the water surface uniformly in the Wagner pot. Further, 5 days after the transplantation, an amount equivalent to 40 gai / 10a of benzobicyclone wettable powder prepared according to Example 2 was sprayed on the water surface uniformly in the Wagner pot. 28 days after transplantation, the degree of inhibition of rice growth was examined in comparison with the control group and the untreated group, and the results are shown in Table 11.

Example 9
A 1 / 5000a Wagner pot was filled with paddy field soil (Korean soil), and the water depth was kept at 4 cm after entering water and scuffing. The next day, rice (Ginnan style) grown to the second leaf stage using the seedling culture soil was transplanted so that the root portion was cut to a length of 0.5 cm and the depth of the base portion was 1 cm. On the next day after transplantation, a wettable powder 120gai / 10a equivalent amount of the compound represented by the general formula [I] (compound No. 51) prepared according to Example 1 was sprayed on the water surface uniformly in the Wagner pot. Further, 5 days after transplantation, the equivalent amount of benzobicyclone wettable powder 20gai / 10a prepared according to Example 2 was sprayed on the water surface uniformly in the Wagner pot. 28 days after transplantation, the degree of inhibition of rice growth was examined in comparison with the control group and the untreated group, and the results are shown in Table 12.

Example 10
A 1 / 5000a Wagner pot was filled with paddy field soil (Korean soil), and the water depth was kept at 4 cm after entering water and scuffing. The next day, rice grown up to the second leaf stage using seedling culture soil (Ginnam-style)
The root portion was cut to a length of 0.5 cm and transplanted so that the depth of the base portion was 3 cm. On the next day after transplantation, a wettable powder 240gai / 10a equivalent amount of the compound represented by the general formula [I] (compound number: 51) prepared according to Example 1 was sprayed on the water surface uniformly in the Wagner pot. Further, 5 days after the transplantation, an amount equivalent to 10 gai / 10a of bensulfuron methyl wettable powder prepared according to Example 2 was sprayed on the water surface uniformly in the Wagner pot. 28 days after transplantation, the degree of inhibition of rice growth was examined in comparison with the control group and untreated group, and the results are shown in Table 13.

Example 11
A 1 / 5000a Wagner pot was filled with paddy field soil (Korean soil), and the water depth was kept at 4 cm after entering water and scuffing. The next day, rice (Ginnan style) grown to the second leaf stage using the seedling culture soil was transplanted so that the root portion was cut to a length of 0.5 cm and the depth of the base portion was 3 cm. On the day after transplantation, the surface of the compound represented by the general formula [I] prepared according to Example 1 (Compound Nos. 51 and 53) equivalent to the wettable powder 240gai / 10a was sprayed on the water surface so as to be uniform in the Wagner pot. did. Further, 5 days after transplantation, an amount equivalent to 5 gai / 10a of pyrimylsulfan wettable powder was sprayed on the water surface so as to be uniform in the Wagner pot. 28 days after transplantation, the degree of inhibition of rice growth was examined in comparison with the control group and untreated group, and the results are shown in Table 14.
Pyrimisulphan wettable powder was prepared in the same manner using pyrimylsulfan instead of compound No. 2 in Example 2.

Example 12
A 1 / 5000a Wagner pot was filled with paddy field soil (Korean soil), and after entering water and plowing, dormant awakened firefly seeds were sown at a depth of 0.5 to 1.0 cm, and the water depth was maintained at 4 cm. On the day after sowing, the surface of the compound represented by the general formula [I] prepared according to Example 1 (Compound Nos. 51 and 53) equivalent to the wettable powder 240gai / 10a was sprayed on the water surface uniformly. did. Four days after spraying, the equivalent of 12.5 gai / 10a benzobicyclon wettable powder prepared according to Example 2 was sprayed on the water surface uniformly in the Wagner pot. The herbicidal effect was investigated according to the survey criteria shown in Table 15 after 26 days of benzobicyclone wettable powder application, and the results are shown in Table 16.

  From Tables 8 to 14 and Table 16, the test group to which the compound represented by the general formula [I] was added had less rice growth inhibition compared to the comparative group using only the herbicidally active compound. Reduces the phytotoxicity of herbicides without reducing the herbicidal effects of herbicides. From this, the usefulness of the phytotoxicity reducing agent of the present invention can be confirmed.

  Examples of various preparations of the herbicidal composition of the present invention are shown below. In addition, about each composition component, a part means a mass part.

Example 13
Pyrimisulfurone (1 part), Compound No. 51 (35 parts), pregelatinized starch (3 parts), calcium carbonate (20 parts), clay (41 parts), kneaded after adding an appropriate amount of water, extruded granulation The resulting mixture was granulated by extrusion from a screen having an opening diameter of 1 mm using a machine, dried at a product temperature of 60 ° C. with a fluidized bed dryer, and sieved to obtain a granule containing pyrimisulfurphan and compound number 51.

Example 14
Bensulfuron methyl (0.7 parts), compound number 51 (30 parts), enzyme-modified dextrin (3 parts), calcium carbonate (20 parts), clay (46.3 parts) were added with an appropriate amount of water and kneaded. Thereafter, the mixture is extruded and granulated from a screen having an opening diameter of 1 mm using an extrusion granulator, dried in a fluidized bed dryer at a product temperature of 60 ° C., and sieved to contain bensulfuron methyl and compound number 51. A granule was obtained.

Example 15
Bensulfuron methyl (0.7 parts), Compound No. 53 (30 parts), pregelatinized starch (3 parts), dioctylsulfosuccinate sodium salt (1 part), calcium carbonate (20 parts), clay (45.3) Part) was added and kneaded with an appropriate amount of water, and then extruded and granulated from a screen having an opening diameter of 1 mm using an extrusion granulator, dried at a product temperature of 60 ° C. with a fluidized bed dryer, and sieved. Granules containing bensulfuron methyl and compound no. 53 were obtained.

Example 16
Benzobicyclone (1 part), Compound No. 53 (10 parts), Enzyme-modified dextrin (3 parts), Sodium dodecylbenzenesulfonate (1 part), Calcium carbonate (85 parts) A granule containing benzobicyclone and compound No. 53 by extrusion granulation from a screen having an opening diameter of 1 mm using an extrusion granulator, drying with a fluidized bed dryer at a product temperature of 60 ° C., and sieving. Got.

Example 17
Bensulfuron methyl (0.7 parts), compound number 92 (35 parts), pregelatinized starch (3 parts), calcium carbonate (41 parts) and clay (20.3 parts) were added with an appropriate amount of water and kneaded. Thereafter, the mixture is extruded and granulated from a screen having an opening diameter of 1 mm using an extrusion granulator, dried in a fluidized bed dryer at a product temperature of 60 ° C., and sieved to contain bensulfuron methyl and compound number 92. A granule was obtained.

Example 18
Pyrimisulphan (1 part), Compound No. 53 (30 parts), pregelatinized starch (3 parts), distearyldimethylammonium chloride (5 parts), clay (20 parts), calcium carbonate (41 parts) in an appropriate amount of water And then kneaded, extruded and granulated from a screen with an opening diameter of 1 mm using an extrusion granulator, dried in a fluidized bed dryer at a product temperature of 60 ° C., and sieved to obtain pyrimyl fan and compound number. A granule containing 53 was obtained.

Example 19
Benzobicyclone (2 parts), Compound No. 53 (24 parts), pregelatinized starch (3 parts), dioctyl sulfosuccinate sodium salt (3 parts), clay (10 parts), calcium carbonate (58 parts) After adding water and kneading, it is extruded and granulated from a screen with an opening diameter of 1 mm using an extrusion granulator, dried in a fluidized bed dryer at a product temperature of 60 ° C., and sieved to obtain benzobicyclone and a compound. A granule containing number 53 was obtained.

Example 20
Benzobicyclone (2 parts), Compound No. 51 (20 parts), polyoxyethylene styrylphenyl ether sulfate sodium salt (5 parts), propylene glycol (10 parts), xanthan gum (0.3 parts), water (62.7) Part) was mixed and pulverized using glass beads as a pulverizing medium using a wet pulverizer to obtain a flowable agent containing benzobicyclone and compound No. 51.

Example 21
Pyrimisulphan (1 part), compound number 92 (37 parts), enzyme-modified dextrin (3 parts), sodium dodecylbenzenesulfonate (1 part), bentonite (14 parts), calcium carbonate (44 parts) with appropriate amount of water And then kneaded, extruded and granulated from a screen with an opening diameter of 1 mm using an extrusion granulator, dried in a fluidized bed dryer at a product temperature of 60 ° C., and sieved to obtain pyrimyl fan and compound number. A granule containing 92 was obtained.

Example 22
Benzobicyclone (2 parts), Compound No. 51 (20 parts), enzyme-modified dextrin (3 parts), sodium dodecylbenzenesulfonate (1 part), bentonite (20 parts), calcium carbonate (54 parts) And kneaded, and then extruded and granulated from a screen with an opening diameter of 1 mm using an extrusion granulator, dried in a fluidized bed dryer at a product temperature of 60 ° C., and sieved to obtain benzobicyclone and compound number. A granule containing 51 was obtained.

Example 23
Add appropriate amount of water to tenyl chlor (1 part), compound number 53 (10 parts), enzyme-modified dextrin (3 parts), sodium dodecylbenzenesulfonate (1 part), bentonite (25 parts), calcium carbonate (60 parts) After kneading, the mixture is extruded and granulated from a screen having an opening diameter of 1 mm using an extrusion granulator, dried with a fluidized bed dryer at a product temperature of 60 ° C., and sieved to contain tenyl chlor and compound number 53. A granule was obtained.

Example 24
AVH-301 (1 part), Compound No. 51 (10 parts), enzyme-modified dextrin (3 parts), sodium dodecylbenzenesulfonate (1 part), bentonite (25 parts), calcium carbonate (60 parts) After kneading and extruding from a screen with an opening diameter of 1 mm using an extrusion granulator, drying with a fluidized bed dryer at a product temperature of 60 ° C., and sieving, AVH-301 and compound number A granule containing 51 was obtained.

Example 25
Bensulfuron methyl (0.2 parts), Compound No. 92 (8 parts), enzyme-modified dextrin (3 parts), sodium dodecylbenzenesulfonate (1 part), bentonite (25 parts), calcium carbonate (62.8 parts) After adding an appropriate amount of water to kneading, extrusion granulation from a screen with an opening diameter of 1 mm using an extrusion granulator, drying with a fluidized bed dryer at a product temperature of 60 ° C., and sieving Granules containing ruflon methyl and compound no. 92 were obtained.

Example 26
AVH-301 (1 part), Compound No. 53 (10 parts), enzyme-modified dextrin (3 parts), sodium dodecylbenzenesulfonate (1 part), bentonite (30 parts), calcium carbonate (55 parts) with appropriate amount of water And then kneading and extruding from a screen having an opening diameter of 1 mm using an extrusion granulator, drying in a fluidized bed dryer at a product temperature of 60 ° C., and sieving to obtain a herbicidal active compound AVH-301. And a granule containing Compound No. 53 was obtained.

Example 27
Add appropriate amount of water to tenyl chlor (1 part), compound number 51 (20 parts), enzyme-modified dextrin (3 parts), sodium dodecylbenzenesulfonate (1 part), bentonite (25 parts), calcium carbonate (50 parts) After kneading, the mixture is extruded and granulated from a screen having an opening diameter of 1 mm using an extrusion granulator, dried in a fluidized bed dryer at a product temperature of 60 ° C., and sieved to contain tenyl chlor and compound number 51. A granule was obtained.

Example 28
Herbicidally active compound benzobicyclone (1 part) and herbicidally active compound cavenstrol (1 part), Compound No. 53 (30 parts), enzyme-modified dextrin (3 parts), sodium dodecylbenzenesulfonate (1 part), bentonite (20 parts) ) After adding an appropriate amount of water to calcium carbonate (44 parts) and kneading, it is extruded and granulated from a screen with an opening diameter of 1 mm using an extrusion granulator, and dried in a fluidized bed dryer at a product temperature of 60 ° C. By sieving, a granule containing the herbicidally active compound benzobicyclon, fenfentrol, and compound number 53 was obtained.

Example 29
Bensulfuron methyl (1 part) and herbicidally active compound oxadichromephone (2 parts), Compound No. 51 (40 parts), enzyme-modified dextrin (3 parts), sodium dodecylbenzenesulfonate (1 part), bentonite (15 parts), After adding an appropriate amount of water to calcium carbonate (38 parts) and kneading, it is extruded and granulated from a screen with an opening diameter of 1 mm using an extrusion granulator, dried at a product temperature of 60 ° C. with a fluidized bed dryer, and sieved. By dividing, a granule containing bensulfuron methyl, oxadichromephone and compound No. 51 was obtained.

Example 30
AVH-301 (6 parts), compound number 92 (40 parts), sodium alkylnaphthalene sulfonate (10 parts), diatomaceous earth (10 parts) and clay (34 parts) were kneaded with an appropriate amount of water, then extruded. Granulation hydration containing AVH-301 and Compound No. 92 by extruding and granulating from a screen with an aperture diameter of 0.6 mm using a granulator, drying with a fluidized bed dryer at a product temperature of 60 ° C., and sieving An agent was obtained.

Example 31
Bensulfuron methyl (0.5 parts), Compound No. 92 (50 parts), Sodium alkylnaphthalene sulfonate (5 parts), Sodium lauryl sulfate (5 parts), Diatomaceous earth (10 parts), Clay (29.5 parts) Was mixed and pulverized using an impact pulverizer to obtain a wettable powder containing bensulfuron methyl and Compound No. 92.

Example 32
Tenylchlor (1 part), Pentoxazone (1 part), Compound No. 53 (20 parts), Sodium polyoxyethylene styrylphenyl ether sulfate (15 parts), Propylene glycol (10 parts), Xanthan gum (0.2 parts), Water ( 52.8 parts) was mixed and pulverized using glass beads as a pulverization medium using a wet pulverizer to obtain a flowable agent containing tenyl chlor, pentoxazone and compound No. 53.

Example 33
Benzobicyclone (3 parts), Bensulfuron methyl (1 part), Compound No. 53 (50 parts), Enzyme-modified dextrin (2 parts), Acetylenediol (3 parts), Hydrous plastic hollow body (10 parts), Anhydrous Sodium sulfate (15 parts) and urea (16 parts) were mixed with an appropriate amount of water, kneaded, and then extruded and granulated from a screen having an opening diameter of 5 mm using an extrusion granulator to adjust the length to 3 to 20 mm. After that, it was dried in a fluidized bed dryer at a product temperature of 60 ° C. and sieved to obtain a floating diffusion type granule containing benzobicyclone, bensulfuron methyl and compound number 53.

Example 34
Pyriminobac methyl (1 part), Compound No. 53 (30 parts), Enzyme-modified dextrin (3 parts), Sodium dodecylbenzenesulfonate (1 part), Bentonite (20 parts) and Calcium carbonate (45 parts) And then kneaded, extruded and granulated from a screen with an aperture diameter of 1 mm using an extrusion granulator, dried in a fluidized bed dryer at a product temperature of 60 ° C., and sieved to give pyriminobac methyl and compound number A granule containing 53 was obtained.

Example 35
Pyrazosulfuron / ethyl (0.7 parts), compound number 2 (30 parts), sodium alkylnaphthalenesulfonate (10 parts), diatomaceous earth (15 parts) and clay (44.3 parts) were added with an appropriate amount of water and kneaded. After that, it is extruded and granulated from a screen with an aperture diameter of 0.6 mm using an extrusion granulator, dried in a fluidized bed dryer at a product temperature of 60 ° C., and sieved to contain pyrazosulfuron-ethyl and compound number 2 A granulated wettable powder was obtained.

Example 36
Halosulfuron methyl (0.5 parts), Compound No. 17 (50 parts), sodium alkylnaphthalene sulfonate (5 parts), sodium lauryl sulfate (5 parts), diatomaceous earth (10 parts) and clay (29.5 parts) Was mixed and pulverized using an impact pulverizer to obtain a wettable powder containing halosulfuron methyl and Compound No. 17.

Example 37
Add appropriate amount of water to fentolazamide (3 parts), Compound No. 51 (30 parts), enzyme-modified dextrin (3 parts), sodium dodecylbenzenesulfonate (1 part), bentonite (20 parts) and calcium carbonate (43 parts) After kneading, the mixture is extruded and granulated from a screen having an opening diameter of 1 mm using an extrusion granulator, dried with a fluidized bed dryer at a product temperature of 60 ° C., and sieved to contain fentolazamide and compound number 51. A granule was obtained.

Example 38
Thiobencarb (16 parts), compound number 7 (8 parts), enzyme-modified dextrin (3 parts), sodium dodecylbenzenesulfonate (1 part), fumed silica (white carbon) (5 parts), diatomaceous earth (5 parts), bentonite (20 parts) and calcium carbonate (42 parts) after adding an appropriate amount of water and kneading, using an extrusion granulator, extrusion granulation is performed from a screen having an opening diameter of 1 mm, and a fluidized bed dryer at a product temperature of 60 ° C. And dried and sieved to obtain granules containing thiobencarb and Compound No. 7.

Example 39
Penox slam (0.2 parts), compound number 70 (20 parts), enzyme-modified dextrin (3 parts), sodium dodecylbenzenesulfonate (1 part), bentonite (25 parts) and calcium carbonate (50.8 parts) After adding water and kneading, the mixture was extruded and granulated from a screen with an opening diameter of 1 mm using an extrusion granulator, dried at a product temperature of 60 ° C. with a fluidized bed dryer, and sieved to obtain penox slam and compound number. A granule containing 70 was obtained.

Next, the example is shown about the phytotoxicity reduction method of the herbicide by this invention.

Example 40
Add an appropriate amount of water to bensulfuron methyl (0.7 parts), pregelatinized starch (3 parts), clay (20 parts), calcium carbonate (76.3 parts), knead, and then use an extrusion granulator. Then, the mixture was granulated by extrusion from a screen having an opening diameter of 1 mm, dried with a fluidized bed dryer at a product temperature of 60 ° C., and sieved to obtain a granule containing bensulfuron methyl. Separately, Compound No. 53 (30 parts), alkylnaphthalenesulfonic acid sodium salt (2 parts), diatomaceous earth (20 parts), and clay (48 parts) were mixed and pulverized using an impact pulverizer to obtain Compound No. 53. A wettable powder was obtained. This granule and wettable powder were simultaneously applied to paddy weeds.

Example 41
The granule containing bensulfuron methyl produced in Example 40 was applied to paddy weed, and after 3 days, the wettable powder containing Compound No. 53 produced in Example 40 was applied to paddy weed.

Example 42
The wettable powder containing Compound No. 53 produced in Example 40 was applied to paddy weed, and after 2 weeks, the granule containing bensulfuron methyl produced in Example 40 was applied to paddy weed.

Claims (21)

Formula [I]

[Wherein Y represents an oxygen atom or a sulfur atom,
R ¹ is a C ₁ -C ₁₆ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₁₀ haloalkyl group, or a C ₁ -C _6. cyanoalkyl _group, C 3 -C ₆ cycloalkyl _C 1 -C ₆ alkyl _group, C 1 -C ₆ alkoxy _C 1 -C ₆ alkyl _group, C 1 -C ₆ alkylthio _C 1 -C ₆ alkyl group, a phenyl group ( The group may be substituted with a halogen atom, a nitro group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ alkylthio group, or a C ₁ -C ₆ alkoxycarbonyl group. , -WQ group, -Q ¹ group or -W-Q ¹ group,
W _represents a C 1 -C ₆ alkyl group,
Q is phenyl (in which the group, a halogen atom, a nitro group, a cyano _group, C 1 -C _{6 alkyl,} C 1 -C ₆ alkoxy _group, C 1 -C ₆ haloalkyl _group, C 1 -C ₆ haloalkoxy Group may be substituted with a group or a —NR ² R ³ group),
Q ¹ represents a heterocyclic group having 3 to 10 carbon atoms having one or more hetero atoms selected from the same or different oxygen, sulfur and nitrogen atoms (the group is a halogen atom, a nitro group, (It may be substituted with a cyano group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ haloalkoxy group or a —NR ² R ³ group.) are shown, X is a halogen atom, a nitro group, a cyano _group, C 1 -C _{6 alkyl,} C 1 -C ₆ alkoxy _group, C 1 -C ₆ haloalkyl _group, C 1 -C ₆ haloalkoxy group or -NR ² R represents a group ³
R ² and R ³ are each independently a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group or a phenyl group (the group is a halogen atom, a nitro group, a cyano group, C ₁ -C _6). An alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ haloalkoxy group or a —NR ⁴ R ⁵ group, which may be substituted).
R ⁴ and R ⁵ each independently represent a hydrogen atom or a C ₁ -C ₆ alkyl group,
n represents an integer of 0 to 4. ]
A herbicide safener comprising a 1,2-benzisothiazolin-3-one 1,1-dioxide derivative represented by the formula: or a salt thereof as an active ingredient. In general formula [I],
Y is an oxygen atom,
R ¹ is a C ₁ -C ₁₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, a phenyl group (the group is a halogen atom, a nitro group, a C _1- A C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ alkylthio group, a C ₁ -C ₆ alkoxycarbonyl group), a -WQ group, a -Q ¹ group or- a ^{W-Q 1} group,
W is _C 1 -C ₆ alkyl group,
Q is a phenyl group (the group is a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ haloalkoxy group) Or may be substituted with a —NR ² R ³ group).
Q ¹ is a heterocyclic group having 3 to 10 carbon atoms having one or more heteroatoms selected from oxygen, sulfur and nitrogen atoms which may be the same or different (the group is a halogen atom, a nitro group, a cyano group, Group, C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ haloalkoxy group or —NR ² R ³ group may be substituted). Show
X is a halogen atom, a nitro group, a cyano _group, C 1 -C _{6 alkyl,} C 1 -C ₆ alkoxy _group, C 1 -C ₆ haloalkyl _group, C 1 -C ₆ haloalkoxy group or a ^-NR 2 ^{R 3} group And
R ² and R ³ are each independently a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group or a phenyl group (the group is a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group) Group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ haloalkoxy group or a —NR ⁴ R ⁵ group).
R ⁴ and R ⁵ are each independently a hydrogen atom or a C ₁ -C ₆ alkyl group,
n is an integer from 0 to 4,
The safener of a herbicide according to claim 1. In general formula [I],
Y is an oxygen atom,
R ¹ is a C ₁ -C ₁₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, a -WQ group, a -Q ¹ group or -WQ ¹ And W is a C ₁ -C ₃ alkyl group,
Q is a phenyl group (the group is a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group or a C ₁ -C ₆ haloalkoxy group) And may be substituted with
Q ¹ is a heterocyclic group having 3 to 6 carbon atoms having one or more heteroatoms selected from oxygen atom, sulfur atom and nitrogen atom which may be the same or different (the group is a halogen atom, nitro group, cyano group Group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group or a C ₁ -C ₆ haloalkoxy group).
X is a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group or a C ₁ -C ₆ haloalkoxy group,
n is an integer from 0 to 4,
The safener of a herbicide according to claim 1. In general formula [I],
Y is an oxygen atom,
R ¹ is a C ₁ -C ₁₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, a -WQ group or a -WQ ¹ group,
W is _C 1 -C ₃ alkyl group,
Q is a phenyl group (the group is a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group or a C ₁ -C ₆ haloalkoxy group) And may be substituted with
Q ¹ is a heterocyclic group having 3 to 6 carbon atoms having one or more heteroatoms selected from oxygen atom, sulfur atom and nitrogen atom which may be the same or different (the group is a halogen atom, nitro group, cyano group Group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group or a C ₁ -C ₆ haloalkoxy group).
n is 0,
The safener of a herbicide according to claim 1. In general formula [I],
Y is an oxygen atom,
R ¹ is a C ₁ -C ₁₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group or a -WQ group,
W is _C 1 -C ₃ alkyl group,
Q is a phenyl group (the group is a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkyl group or a C ₁ -C ₆ haloalkoxy group) And may be substituted with
n is 0,
The safener of a herbicide according to claim 1. In general formula [I],
Y is an oxygen atom,
R ¹ is a C ₁ -C ₁₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group or a -WQ group,
W is _C 1 -C ₂ alkyl group,
Q is phenyl (in which the group, a halogen atom, a nitro group, a cyano _group, C 1 -C _{6 alkyl,} C 1 -C ₆ alkoxy group) may be substituted with. ) And
n is 0,
The safener of a herbicide according to claim 1. In general formula [I],
Y is an oxygen atom,
R ¹ is a C ₁ -C ₁₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group or a -WQ ¹ group,
W is _C 1 -C ₂ alkyl group,
Q ¹ represents a pyridyl group (the group may be substituted with a halogen atom);
n is 0,
The safener of a herbicide according to claim 1. (A) 1,2-benzisothiazolin-3-one 1,1-dioxide derivative represented by the general formula [I] according to any one of claims 1 to 7, or a salt thereof;
(B) Pyrimisulphane, benzobicyclone, oxadichromephone, sulfonylurea compound, triazolopyrimidine compound, pyrimidinyloxy (thio) benzoic acid compound, triketone compound, chloroacetamide compound, oxazolidinedione compound, triazole Compound, thiocarbamate compound, tetrazolinone compound, isoxazoline derivative having the general formula [II] or a pharmacologically acceptable salt thereof:

{Wherein n represents an integer of 0 to 2, m represents an integer of 1 to 3, and R ⁵ and R ⁶ are independently of each other a hydrogen atom, a cyano group, an alkoxycarbonyl group, C ₁ -C ₆ It represents an alkyl group, a halogen atom or a _C 1 -C ₆ haloalkyl group,
R ¹ and R ² are each a hydrogen atom, a [C ₃ -C ₈ cycloalkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ alkylcarbonyl group, a C ₁ -C ₆ alkylthio group, a C ₁ -C ₆ alkylsulfinyl _group, C 1 -C ₆ alkylsulfonyl _group, C 1 -C ₆ alkylamino group, di _(C 1 -C ₆ alkyl) amino group, a hydroxyl group, a cyano _group, C 1 -C ₆ alkoxycarbonyl group, _{C 1} -C ₆ alkylaminocarbonyl group, di (C ₁ -C ₆ alkyl) aminocarbonyl group, (C ₁ -C ₆ alkylthio) carbonyl group, carboxyl group, (optionally substituted) benzyloxy group, (substituted) may be) phenoxy group or (optionally substituted by substituted may be) phenyl] C ₁ -C ₈ alkyl group, C ₃ -C ₈ consequent Alkyl _group, C 1 -C ₆ alkoxycarbonyl _group, C 1 -C ₆ alkylamino group, di _(C 1 -C ₆ alkyl) aminocarbonyl _group, C 1 -C ₆ alkyl thiocarbonyl group, is a carboxyl group or a substituted Or R ¹ and R ² together with these bonded carbon atoms may form a C ₃ -C ₇ spiro ring,
R ³ and ^{R 4} are hydrogen atoms, (the same or different 1 to 3 halogen _atoms, C 3 -C ₈ optionally substituted cycloalkyl group or a _C 1 -C ₆ alkoxy group) _{C 1} - C ₈ alkyl or _C 3 -C ₈ cycloalkyl, ^{R 3} and ^{R 4} may form a spiro ring of _C 3 -C ₇ with these bonded carbon atoms, or ^R 1, ^{R 2} , R ³ and R ⁴ together with these bonded carbon atoms may form a 5- to 8-membered ring,
Y is a hydrogen atom, a C ₁ -C ₆ alkoxycarbonyl group, a carboxyl group, a C ₂ -C ₆ alkenyl group, [1 to 3 halogen atoms that are the same or different, a C ₁ -C ₆ alkoxy group, a C _2- A C ₆ alkenyloxy group, a C ₂ -C ₆ alkynyloxy group, a benzyloxy group (which may be substituted), a C ₁ -C ₆ alkoxycarbonyl group, a carboxyl group, a hydroxyl group or a formyl group. A C ₁ -C ₁₀ alkyl group or a phenyl group (substituted with 1 to 5 identical or different R ⁷ ),
R ⁷ represents a hydrogen atom, [1 to 3 halogen atoms that are the same or different, a C ₁ -C ₆ alkoxy group, a hydroxyl group, a C ₁ -C ₆ alkylthio group, a C ₁ -C ₆ alkylsulfinyl group, a C _1- C ₆ alkylsulfonyl group, C ₁ -C ₆ alkylamino group, di (C ₁ -C ₆ ) alkylamino group, cyano group or (optionally substituted) may be substituted with phenoxy] C _1- C ₆ alkyl group, (1 to 3 halogen atoms which are the same or different, C ₁ -C ₆ alkoxy group, C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, C ₁ -C ₆ alkoxycarbonyl group A C ₁ -C ₆ alkylcarbonyl group or a C ₃ -C ₈ cycloalkyl group, which may be substituted with a C ₁ -C ₆ alkoxy group, a C ₂ -C ₆ alkenyl group, or a C ₃ -C ₈ cycloalkyl group, (identical or different 1 to may 3 is substituted with a halogen atom or a _C 1 -C ₆ alkoxy _group) C 1 -C ₆ alkylthio group, (identical or different 1 C ₁ -C ₆ alkylsulfinyl group (optionally substituted with 3 to 3 halogen atoms or C ₁ -C ₆ alkoxy groups), 1 to 3 halogen atoms or the same or different C ₁ -C ₆ alkoxy groups C ₁ -C ₆ alkylsulfonyl group (which may be substituted with a group), benzyloxy group (which may be substituted), (C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ alkylcarbonyl _(C 1 -C ₆ alkyl) may be substituted with a group or _C 1 -C ₆ alkylsulfonyl _(C 1 -C ₆ alkyl) group) a Mino group, di (C ₁ -C ₆ alkyl) amino group, halogen atom, cyano group, nitro group, C ₁ -C ₆ alkoxycarbonyl group, C ₃ -C ₈ cycloalkyloxycarbonyl group, carboxyl group, C _2- C ₆ alkenyloxycarbonyl group, C ₂ -C ₆ alkynyloxycarbonyl group, (optionally substituted) benzyloxycarbonyl group, (optionally substituted) phenoxycarbonyl group or C ₁ -C ₆ alkylcarbonyloxy group Represents a group. }
And an isoxazoline derivative having the general formula [III] or a pharmacologically acceptable salt thereof:

{Wherein R ¹ and R ² are the same or different and are a hydrogen atom, a C ₁ -C ₁₀ alkyl group, a C ₃ -C ₈ cycloalkyl group or a C ₃ -C ₈ cycloalkyl C ₁ -C ₃ alkyl group. Or R ¹ and R ² together represent a C ₃ -C ₇ spiro ring with these bonded carbon atoms,
R ³ and R ⁴ are the same or different and each represents a hydrogen atom, a C ₁ -C ₁₀ alkyl group or a C ₃ -C ₈ cycloalkyl group, or R ³ and R ⁴ are taken together, Exhibiting a C ₃ -C ₇ spiro ring with bonded carbon atoms, and R ¹ , R ² , R ³ and R ⁴ can also form a 5- to 8-membered ring with these bonded carbon atoms;
R ⁵ and R ⁶ are the same or different and each represents a hydrogen atom, a halogen atom, a C ₁ -C ₁₀ alkyl group or a C ₁ -C ₆ haloalkyl group,
Y represents a 5- to 6-membered aromatic heterocyclic group or an aromatic hetero-fused cyclic group having an arbitrary hetero atom selected from a nitrogen atom, an oxygen atom and a sulfur atom, and these heterocyclic groups are substituted with a substituent group α And may be substituted with 0 to 6 identical or different groups selected from each other, and adjacent alkyl groups, alkoxy groups, alkyl groups and alkoxy groups, alkyl groups and alkylthio groups, alkyl groups and An alkylsulfonyl group, an alkyl group and a monoalkylamino group or an alkyl group and a dialkylamino group may be bonded to form a 5- to 8-membered ring which may be substituted with 1 to 4 halogen atoms; Moreover, when the hetero atom of these heterocyclic groups is a nitrogen atom, it may be oxidized to N-oxide,
n represents an integer of 0 to 2. }
`` Substituent group α ''
A hydroxyl group, a thiol group, a halogen _atom, C 1 _{-C 10} alkyl groups, mono-substituted by any group selected from Substituent group β a _C 1 _{-C 10} alkyl _group, C 1 -C ₄ haloalkyl groups, _{C 3} -C ₈ cycloalkyl _group, C 1 _{-C 10} alkoxy group, mono-substituted by any group selected from substituent group γ the _C 1 _{-C 10} alkoxy _group, C 1 -C ₄ haloalkoxy groups, _{C 3} -C ₈ cycloalkyl _group, C 3 -C ₈ cycloalkyl _C 1 -C ₃ alkyl _group, C 1 _{-C 10} alkylthio group, _{C 1} which is mono-substituted by any group selected from substituent group γ -C ₁₀ alkylthio _group, C 1 -C ₄ haloalkylthio _group, C 2 -C ₆ alkenyl _group, C 2 -C ₆ alkenyloxy _group, C 2 -C ₆ alkynyl _group, C 2 -C ₆ Arukiniruoki _Group, C 1 _{-C 10} alkylsulfinyl group, mono-substituted by any group selected from Substituent group γ the _C 1 _{-C 10} alkylsulfinyl _group, C 1 _{-C 10} alkylsulfonyl group, from Substituent group γ C ₁ -C ₁₀ alkylsulfonyl group monosubstituted with any selected group, C ₁ -C ₄ haloalkylsulfinyl group, C ₁ -C ₁₀ monosubstituted with any group selected from substituent group γ an alkylsulfonyloxy group, C ₁ -C ₄ haloalkylsulfonyl groups, C ₁ -C ₁₀ alkyl sulfonyloxy group, C ₁ -C ₄ haloalkylsulfonyl group, an optionally substituted phenyl group, optionally substituted phenoxy Group, phenylthio group which may be substituted, aromatic heterocyclic group which may be substituted, aromatic which may be substituted Heterocyclic oxy group, optionally substituted aromatic heterocyclic thio group, optionally substituted phenylsulfinyl group, optionally substituted phenylsulfonyl group, optionally substituted aromatic heterocyclic sulfonyl group , optionally substituted phenylsulfonyloxy group, acyl groups, C ₁ -C ₄ haloalkylcarbonyl group, an optionally substituted benzylcarbonyl group, optionally substituted benzoyl group, carboxyl groups, C ₁ -C ₁₀ alkoxycarbonyl group, optionally substituted benzyloxycarbonyl group, optionally substituted phenoxycarbonyl group, cyano group, carbamoyl group (the nitrogen atom of the group is the same or different, C ₁ -C ₁₀ alkyl group Alternatively, it may be substituted with an optionally substituted phenyl group. ), C ₁ -C ₆ acyloxy group, C ₁ -C ₄ haloalkylcarbonyloxy group, optionally substituted benzylcarbonyloxy group, optionally substituted benzoyloxy group, nitro group, amino group (of the group) nitrogen atom may be the same or _different, C 1 _{-C 10} alkyl group, optionally substituted _phenyl, C 1 -C ₆ acyl _group, C 1 -C ₄ haloalkylcarbonyl group, optionally benzylcarbonyl optionally substituted group, substituted by an optionally substituted benzoyl groups, C ₁ -C ₁₀ alkyl sulfonyl group, C ₁ -C ₄ haloalkylsulfonyl groups, optionally substituted benzylsulfonyl group or an optionally substituted phenylsulfonyl group May be.)
"Substituent group β"
_Hydroxyl, C 3 -C ₈ cycloalkyl group (which may be substituted with a halogen atom or an alkyl _group), C 1 _{-C 10} alkoxy _group, C 1 _{-C 10} alkylthio _groups, C 1 _{-C 10} alkyl sulfonyl A group, a C ₁ -C ₁₀ alkoxycarbonyl group, a C ₂ -C ₆ haloalkenyl group, an amino group (the nitrogen atom of the group is the same or different, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₆ acyl group, A C ₁ -C ₄ haloalkylcarbonyl group, a C ₁ -C ₁₀ alkylsulfonyl group, which may be substituted with a C ₁ -C ₄ haloalkylsulfonyl group, a carbamoyl group (the nitrogen atom of the group is the same or different, and ₁ -C ₁₀ optionally substituted with an alkyl _group), C 1 -C ₆ acyl _group, C 1 -C ₄ haloalkylcarbonyl _group, C 1 _{-C 10} alkoxy Amino group, a cyano group, a phenyl group which may be substituted, an optionally substituted phenoxy group "substituent group γ"
C ₁ -C ₁₀ alkoxycarbonyl group, an optionally substituted phenyl group, an optionally substituted aromatic heterocyclic group, a cyano group, a nitrogen atom of the carbamoyl group (in which the same or different, C ₁ - it may be substituted with C ₁₀ alkyl group.)
A herbicide composition with reduced phytotoxicity, comprising at least one herbicidal active compound selected from the group consisting of: The sulfonylurea compound is
Amidosulfuron, azimusulfuron, bensulfuron methyl, chlorimuron ethyl, chlorsulfuron, synosulfuron, cyclosulfamuron, ethamethsulfuron methyl, ethoxysulfuron, flazasulfuron, flupirsulfuron, foramsulfuron, halos Ruflon methyl, imazosulfuron, iodosulfuron, mesosulfuron methyl, metsulfuron methyl, nicosulfuron, oxasulfuron, primsulfuron, prosulfuron, pyrazosulfuron ethyl, rimsulfuron, sulfomethuron methyl, sulfosulfuron, thifensulfuron・ Selected from the group consisting of methyl, trisulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl and tritosulfuron Reduced phytotoxicity herbicidal composition according to claim 8, which is a type even without. Triazolopyrimidine compounds
The herbicidal composition with reduced phytotoxicity according to claim 8, which is at least one selected from the group consisting of chloranthram methyl, diclosram, flora slam, flumethram, methotram, and penox slam. Pyrimidinyloxy (thio) benzoic acid compound is
9. The herbicide composition with reduced phytotoxicity according to claim 8, which is at least one selected from the group consisting of pyrithiobac, pyrithiobac sodium salt, pyriminobac-methyl, bispyribac, bispyribac sodium salt, pyribenzoxime and pyriftalide. Triketone compounds
Mesotrione, sulcotrione or formula

The herbicide composition with reduced phytotoxicity according to claim 8, which is at least one selected from the group consisting of compounds represented by: Chloroacetamide compounds
9. It is at least one selected from the group consisting of propachlor, dimetachlor, metazachlor, tenyl chlor, alachlor, butachlor, pretilachlor, acetochlor, propisochlor, metolachlor, S-metolachlor, dimethenamide and petoxamide. A herbicide composition with reduced phytotoxicity described in 1.   The herbicide composition with reduced phytotoxicity according to claim 8, wherein the oxazolidinedione compound is pentoxazone.   The herbicide composition with reduced phytotoxicity according to claim 8, wherein the triazole-based compound is caffeinetrol. Thiocarbamate compounds
The herbicide with reduced phytotoxicity according to claim 8, wherein the herbicide has at least one selected from the group consisting of pyributycarb, butyrate, cycloate, dimepiperate, EPTC, esprocarb, molinate, olvencarb, pebrate, prosulfocarb, thiobencarb, thiocarbazyl and triate. Composition.   The herbicidal composition with reduced phytotoxicity according to claim 8, wherein the tetrazolinone compound is fentolazamide.   The herbicidal composition according to any one of claims 8 to 17, further comprising a surfactant. A 1,2-benzisothiazolin-3-one 1,1-dioxide derivative represented by the general formula [I] according to any one of claims 1 to 7, or a salt thereof,
(A) whether it is applied simultaneously with the herbicide,
(B) A method for reducing the herbicide's phytotoxicity, wherein the herbicide is applied in proximity to the herbicide, or (c) the seed or seedling of the cultivated plant itself is treated.   The method according to claim 19, wherein the cultivated plant is wheat, rye, barley, oat, rice, corn, sorghum, cotton or soybean. The method according to claim 19, wherein the cultivated plant is paddy rice.