JP5449911B2 - Pest control composition - Google Patents

Description

Background of the Invention

TECHNICAL FIELD The present invention relates to an agricultural and horticulturally useful pest control composition comprising a combination of a compound represented by the formula (I) or a salt thereof and other insecticides, fungicides and the like.

BACKGROUND ART Many pest control agents have been reported so far, but drug-resistant insect species and difficult-to-control insect species have been recognized, and a sufficient control effect has not been obtained. On the other hand, in consideration of the environment and effects on non-target organisms, control with a lower dose is desired.

  So far, a compound represented by the following formula (I) and its insecticidal activity have already been described (Patent Document 1: International Publication No. 2006/13896 pamphlet; Patent Document 2: JP 2008/110953 A). Publication). The Pesticide Manual (The Pesticide Manual, 14th edition, 2006, published by The British Crop Protection Council: Non-Patent Document 1) and Shibuya Index (SHIBUYA INDEX 13th edition, 2008, published by SHIBUYA INDEX RESEARCH GROUP: Non-patent) Reference 2) describes many pest control agents that have been developed and used so far. However, there has been no description so far about the effect of mixing the compound represented by the formula (I) with other pesticides.

International Publication No. 2006/13896 Pamphlet JP 2008/110953 A

The Pesticide Manual, 14th edition, 2006, published by The British Crop Protection Council Shibuya Index (SHIBUYA INDEX 13th edition, 2008, published by SHIBUYA INDEX RESEARCH GROUP)

  The inventors of the present invention have not only lost the activity of each component, but also exhibited a synergistic effect by using the compound represented by the formula (I) and another pesticide in combination. The present inventors have found that it has a remarkably excellent control effect against pests. The present invention is based on this finding.

  Accordingly, it is an object of the present invention to provide a pest control composition that reliably exhibits a control effect on a wider range of pests at a lower application amount.

［式中、
Ｒ_１は、
水素原子、
アルカリ金属、
アルカリ土類金属、
置換されていてもよいＣ_１−１８アルキル基、
置換されていてもよいＣ_２−１８アルケニル基、
置換されていてもよいＣ_２−１８アルキニル基、
置換されていてもよいＣ_３−１０シクロアルキル基、
置換されていてもよいフェニル低級アルキル基、
置換されていてもよいフェノキシ低級アルキル基、
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ヘテロ環基、
ＣＯＲ_４（ここで、Ｒ_４は、
置換されていてもよいＣ_１−１８アルキル基、
置換されていてもよいＣ_２−１８アルケニル基、
置換されていてもよいＣ_２−１８アルキニル基、
置換されていてもよいＣ_３−１０シクロアルキル基、
置換されていてもよいフェニル低級アルキル基、
置換されていてもよいフェノキシ低級アルキル基、
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ヘテロ環基、
置換されていてもよいＣ_１−４アルキルチオ基、
ＯＲ_５（ここで、Ｒ_５は、
置換されていてもよいＣ_１−１８のアルキル基、
置換されていてもよいＣ_２−１８のアルケニル基、
置換されていてもよいＣ_２−１８アルキニル基、
置換されていてもよいＣ_３−１０シクロアルキル基、
置換されていてもよいフェニル低級アルキル基、
置換されていてもよいフェノキシ低級アルキル基、
置換されていてもよいフェニル基、または
置換されていてもよいヘテロ環基を表す）、または
ＮＲ_６Ｒ_７（ここで、Ｒ_６およびＲ_７は、互いに独立して、
水素原子、
置換されていてもよいＣ_１−１８アルキル基、または
置換されていてもよいフェニル基を表す）を表す）、または
ＳＯ_２Ｒ_８（ここで、Ｒ₈は、
置換されていてもよいＣ_１−１８アルキル基、
置換されていてもよいＣ_２−１８アルケニル基、
置換されていてもよいＣ_２−１８アルキニル基、
置換されていてもよいＣ_３−１０シクロアルキル基、
置換されていてもよいフェニル低級アルキル基、
置換されていてもよいフェノキシ低級アルキル基、
置換されていてもよいフェニル基、または
置換されていてもよいヘテロ環基を表す）
を表し、
Ｒ_２は、水素原子、または置換されていてもよいＣ_１−４アルキル基を表し、
Ｒ_３は、
水素原子、
置換されていてもよいＣ_１−１８アルキル基、
置換されていてもよいＣ_２−４アルケニル基、または
置換されていてもよいＣ_１−４アルコキシ基を表し、
ここで、Ｒ_１、Ｒ_２、およびＲ_３において、置換されてもよい基が有する置換基は、ハロゲン原子、Ｃ_１−４アルキルオキシ基、Ｃ_１−４アルキルオキシ−Ｃ_１−４アルキルオキシ基、Ｃ_１−４アルキルオキシカルボニル基、ニトロ基、シアノ基、ホルミル基、トリフルオロメチル基、トリフルオロメトキシ基、アセチル基、アセチルオキシ基、Ｃ_１−４アルキル基（ただし、このＣ_１−４アルキル基は、アルキル基の置換基とはならない）、およびハロゲン原子により置換されていてもよいＣ_３−６シクロアルキル基からなる群から選択されるものであり、
あるいは、Ｒ_２とＲ_３は一緒になって−（ＣＨ_２）_ｍ−（ここで、ｍは３または４を表す）を表し、
Ｘ_１、Ｘ_２、およびＸ_３は、互いに独立して、
水素原子、
ハロゲン原子、
ハロゲン原子により置換されていてもよいＣ_１−４アルキル基、
ハロゲン原子により置換されていてもよいＣ_１−４アルキルオキシ基、
ハロゲン原子により置換されていてもよいＣ_１−４アルキルチオ基、
ハロゲン原子により置換されていてもよいＣ_１−４アルキルオキシカルボニル基、
ニトロ基、または
シアノ基を表し、
ただし、Ｘ_１、Ｘ_２、およびＸ_３は、同時に水素原子を表すことはなく、
Ｗ_１は窒素原子またはＣ−Ｙ_１を表し、
Ｗ_２は窒素原子またはＣ−Ｙ_２を表し、
Ｗ_３は窒素原子またはＣ−Ｙ_３を表し、
ただし、Ｗ_１が窒素原子を表す場合には、Ｗ_２およびＷ_３はそれぞれＣ−Ｙ_２およびＣ−Ｙ_３を表し、Ｗ_２が窒素原子を表す場合には、Ｗ_１およびＷ_３はそれぞれＣ−Ｙ_１およびＣ−Ｙ_３を表し、Ｗ_３が窒素原子を表す場合には、Ｗ_１およびＷ_２はそれぞれＣ−Ｙ_１およびＣ−Ｙ_２を表し、
Ｙ_１、Ｙ_２、Ｙ_３、Ｙ_４、およびＹ_５は、互いに独立して、水素原子、Ａ、またはＢを表し、
ただし、Ｗ_１、Ｗ_２およびＷ_３がそれぞれＣ−Ｙ_１、Ｃ−Ｙ_２およびＣ−Ｙ_３を表し、かつ、Ｚが結合、１つもしくは２つのメチル基で置換されていてもよいメチレン基、または酸素原子を表す場合には、Ｙ_１、Ｙ_２、Ｙ_３、Ｙ_４、およびＹ_５のうち少なくとも１つはＡを表し、
ここで、Ａは、
Ｃ_１−８のアルキル基（このＣ_１−８のアルキル基は、同一もしくは異なる一以上のハロゲン原子、同一もしくは異なる一以上のハロゲン原子により置換されたＣ_１−４アルキルオキシ基、および同一もしくは異なる一以上のハロゲン原子により置換されたＣ_２−４アルケニルオキシ基から選択される一以上の基により置換されたものである）；
Ｃ_２−８のアルケニル基（このＣ_２−８のアルケニル基は、同一もしくは異なる一以上のハロゲン原子、同一もしくは異なる一以上のハロゲン原子により置換されたＣ_１−４アルキルオキシ基、および同一もしくは異なる一以上のハロゲン原子により置換されたＣ_２−４アルケニルオキシ基から選択される一以上の基により置換されたものである）；
Ｃ_１−８アルキルオキシ基（このＣ_１−8アルキルオキシ基は、同一もしくは異なる一以上のハロゲン原子、同一もしくは異なる一以上のハロゲン原子により置換されたＣ_１−４アルキルオキシ基、および同一もしくは異なる一以上のハロゲン原子により置換されたＣ_２−４アルケニルオキシ基から選択される一以上の基により置換されたものである）；
Ｃ_２−８のアルケニルオキシ基（このＣ_２−８のアルケニルオキシ基は、同一もしくは異なる一以上のハロゲン原子、同一もしくは異なる一以上のハロゲン原子により置換されたＣ_１−４アルキルオキシ基、および同一もしくは異なる一以上のハロゲン原子により置換されたＣ_２−４アルケニルオキシ基から選択される一以上の基により置換されたものである）；
Ｃ_１−8アルキルオキシカルボニル基（このＣ_１−8アルキルオキシカルボニル基は、同一もしくは異なる一以上のハロゲン原子、および／または同一もしくは異なる一以上のハロゲン原子により置換されたＣ_１−４アルキルオキシ基により置換されていてもよい）
Ｃ_１−８アルキルチオ基（このＣ_１−８アルキルチオ基は、同一もしくは異なる一以上のハロゲン原子、および／または同一もしくは異なる一以上のハロゲン原子により置換されたＣ_１−４アルキルオキシ基により置換されていてもよい）；
Ｃ_２−８アルケニルチオ基（このＣ_２−８アルケニルチオ基は、同一もしくは異なる一以上のハロゲン原子、および／または同一もしくは異なる一以上のハロゲン原子により置換されたＣ_１−４アルキルオキシ基により置換されていてもよい）；
Ｃ_１−８アルキルスルフィニル基（このＣ_１−８アルキルスルフィニル基は、同一もしくは異なる一以上のハロゲン原子、および／または同一もしくは異なる一以上のハロゲン原子により置換されたＣ_１−４アルキルオキシ基により置換されていてもよい）；
Ｃ_２−８アルケニルスルフィニル基（このＣ_２−８アルケニルスルフィニル基は、同一もしくは異なる一以上のハロゲン原子、および／または同一もしくは異なる一以上のハロゲン原子により置換されたＣ_１−４アルキルオキシ基により置換されていてもよい）；
Ｃ_１−８アルキルスルホニル基（このＣ_１−８アルキルスルホニル基は、同一もしくは異なる一以上のハロゲン原子、および／または同一もしくは異なる一以上のハロゲン原子により置換されたＣ_１−４アルキルオキシ基により置換されていてもよい）；
Ｃ_２−８アルケニルスルホニル基（このＣ_２−８アルケニルスルホニル基は、同一もしくは異なる一以上のハロゲン原子、および／または同一もしくは異なる一以上のハロゲン原子により置換されたＣ_１−４アルキルオキシ基により置換されていてもよい）；
フェニル基（このフェニル基は、同一もしくは異なる一以上のハロゲン原子、同一もしくは異なる一以上のハロゲン原子により置換されたＣ_１−４アルキル基、または同一もしくは異なる一以上のハロゲン原子により置換されたＣ_１−４アルキルオキシ基により置換されたものである）；および
フェノキシ基（このフェノキシ基は、同一もしくは異なる一以上のハロゲン原子、同一もしくは異なる一以上のハロゲン原子により置換されたＣ_１−４のアルキル基、または同一もしくは異なる一以上のハロゲン原子により置換されたＣ_１−４のアルキルオキシ基により置換されたものである）からなる群から選択される基を表し、
Ｂは、ハロゲン原子、Ｃ_１−４アルキル基、Ｃ_１−４アルキルオキシ基、ニトロ基、およびシアノ基からなる群から選択される基を表し、
あるいは、Ｙ_１、Ｙ_２、Ｙ_３、Ｙ_４、およびＹ_５は、隣り合う２つの基が一緒になって、
ハロゲン原子により置換されていてもよい−Ｏ−（ＣＨ_２）_ｎ−Ｏ−、
ハロゲン原子により置換されていてもよい−（ＣＨ_２）_ｎ−Ｏ−、
ハロゲン原子により置換されていてもよい−Ｓ−（ＣＨ_２）_ｎ−Ｓ−、
ハロゲン原子により置換されていてもよい−（ＣＨ_２）_ｎ−Ｓ−、または
ハロゲン原子により置換されていてもよい−（ＣＨ_２）_ｎ−を表してもよく、
ここで、ｎは１、２または３を表し、
Ｚは、結合、酸素原子、硫黄原子、ＳＯ、ＳＯ_２、−Ｑ−、−Ｏ−Ｑ−、−Ｏ−Ｑ−Ｏ−、またはＣＯを表し、
Ｑは、Ｃ_１−４アルキレン基（このＣ_１−４アルキレン基は、ハロゲン原子、シアノ基、またはハロゲン原子で置換されていてもよいＣ_１−４アルキル基により置換されていてもよい）、−（ＣＨ_２）_ｐ−ＣＲ_１０Ｒ_１１−（ＣＨ_２）_ｑ−（Ｒ_１０およびＲ_１１は一緒になって、結合する炭素原子とともに、ハロゲン原子またはハロゲン原子で置換されていてもよいＣ_１−４アルキル基で置換されていてもよいＣ_３−６シクロアルキル基を表し、ｐおよびｑは互いに独立して０〜３の整数を表す）、またはＣ_2−４アルケニレン基（このＣ_２−４アルケニレン基は、ハロゲン原子、シアノ基、またはハロゲン原子で置換されていてもよいＣ_１−４アルキル基により置換されていてもよい）を表す。］
で表される化合物またはその農園芸上許容可能な塩の少なくとも１種と、他の有害生物防除剤の少なくとも１種とを有効成分として含んでなる、有害生物防除用組成物である。 And the composition according to the present invention has the following formula (I):

[Where:
R ₁ is
Hydrogen atom,
Alkali metals,
Alkaline earth metals,
An optionally substituted C _1-18 alkyl group,
An optionally substituted C _2-18 alkenyl group,
An optionally substituted C _2-18 alkynyl group,
An optionally substituted C _3-10 cycloalkyl group,
Optionally substituted phenyl lower alkyl group,
Optionally substituted phenoxy lower alkyl group,
An optionally substituted phenyl group,
An optionally substituted heterocyclic group,
COR ₄ (where R ₄ is
An optionally substituted C _1-18 alkyl group,
An optionally substituted C _2-18 alkenyl group,
An optionally substituted C _2-18 alkynyl group,
An optionally substituted C _3-10 cycloalkyl group,
Optionally substituted phenyl lower alkyl group,
Optionally substituted phenoxy lower alkyl group,
An optionally substituted phenyl group,
An optionally substituted heterocyclic group,
An optionally substituted C _1-4 alkylthio group,
OR ₅ (where R ₅ is
An optionally substituted C _1-18 alkyl group,
An optionally substituted C _2-18 alkenyl group,
An optionally substituted C _2-18 alkynyl group,
An optionally substituted C _3-10 cycloalkyl group,
Optionally substituted phenyl lower alkyl group,
Optionally substituted phenoxy lower alkyl group,
Represents an optionally substituted phenyl group, or an optionally substituted heterocyclic group, or NR ₆ R ₇ (wherein R ₆ and R ₇ are independently of each other;
Hydrogen atom,
Represents a C _1-18 alkyl group which may be substituted, or a phenyl group which may be substituted), or SO ₂ R ₈ (where R ₈ is
An optionally substituted C _1-18 alkyl group,
An optionally substituted C _2-18 alkenyl group,
An optionally substituted C _2-18 alkynyl group,
An optionally substituted C _3-10 cycloalkyl group,
Optionally substituted phenyl lower alkyl group,
Optionally substituted phenoxy lower alkyl group,
Represents a phenyl group which may be substituted, or a heterocyclic group which may be substituted)
Represents
R ₂ represents a hydrogen atom or an optionally substituted C _1-4 alkyl group,
R ₃ is
Hydrogen atom,
An optionally substituted C _1-18 alkyl group,
Represents an optionally substituted _C2-4 alkenyl group, or an optionally substituted _C1-4 alkoxy group,
_Here, in R 1, _{R 2,} and _{R 3,} substituent groups of the group which may be substituted, halogen _{atom, C 1-4 alkyloxy, C 1-4} alkyloxy _{-C 1-4} alkyloxy _{group, C 1-4} alkyloxycarbonyl group, a nitro group, a cyano group, a formyl group, a trifluoromethyl group, a trifluoromethoxy group, an acetyl group, an acetyl _{group, C 1-4} alkyl group (provided that the _{C 1- 4} alkyl group is not a substituent of the alkyl group), and is selected from the group consisting of C _3-6 cycloalkyl group optionally substituted with a halogen atom,
Alternatively, R ₂ and R ₃ together represent — (CH ₂ ) _m — (where m represents 3 or 4),
X ₁ , X ₂ , and X ₃ are independently of each other,
Hydrogen atom,
A halogen atom,
A C _1-4 alkyl group _optionally substituted by a halogen atom,
A C _1-4 alkyloxy group _optionally substituted by a halogen atom,
A C _1-4 alkylthio group optionally substituted by a halogen atom,
A C _1-4 alkyloxycarbonyl group _optionally substituted by a halogen atom,
Represents a nitro group or a cyano group,
However, X ₁ , X ₂ , and X ₃ do not represent a hydrogen atom at the same time,
W ₁ represents a nitrogen atom or C—Y ₁ ,
W ₂ represents a nitrogen atom or C—Y ₂ ,
W ₃ represents a nitrogen atom or C—Y ₃ ,
However, when W ₁ represents a nitrogen atom, W ₂ and W ₃ represent C—Y ₂ and C—Y ₃ , respectively, and when W ₂ represents a nitrogen atom, W ₁ and W ₃ represent each represents _{C-Y 1} and _{C-Y 3,} when _{the W 3} represents a nitrogen atom, _{W 1} and _{W 2} each represents a _{C-Y 1} and _{C-Y 2,}
Y ₁ , Y ₂ , Y ₃ , Y ₄ , and Y ₅ each independently represent a hydrogen atom, A, or B;
Provided that W ₁ , W ₂ and W ₃ represent C—Y ₁ , C—Y ₂ and C—Y ₃ , respectively, and Z is a bond, methylene optionally substituted by one or two methyl groups A group or an oxygen atom, at least one of Y ₁ , Y ₂ , Y ₃ , Y ₄ , and Y ₅ represents A;
Where A is
A C _1-8 alkyl group (the C _1-8 alkyl group is the same or different one or more halogen atoms, a C _1-4 alkyloxy group substituted by one or more same or different halogen atoms, and the same or different One or more groups selected from C _2-4 alkenyloxy groups substituted by one or more different halogen atoms);
A C _2-8 alkenyl group (the C _2-8 alkenyl group is the same or different one or more halogen atoms, a C _1-4 alkyloxy group substituted with one or more same or different halogen atoms, and the same or different One or more groups selected from C _2-4 alkenyloxy groups substituted by one or more different halogen atoms);
C _1-8 alkyloxy group (this C _1-8 alkyloxy group is the same or different one or more halogen atoms, a C _1-4 alkyloxy group substituted with one or more same or different halogen atoms, and the same or different One or more groups selected from C _2-4 alkenyloxy groups substituted by one or more different halogen atoms);
A C _2-8 alkenyloxy group (wherein the C _2-8 alkenyloxy group is one or more same or different halogen atoms, a C _1-4 alkyloxy group substituted by one or more same or different halogen atoms, and Substituted with one or more groups selected from C _2-4 alkenyloxy groups substituted with one or more same or different halogen atoms);
A C _1-8 alkyloxycarbonyl group (the C _1-8 alkyloxycarbonyl group is a C _1-4 alkyloxycarbonyl group substituted with one or more halogen atoms, and / or one or more halogen atoms, the same or different. Optionally substituted by a group)
C _1-8 alkylthio group (this C _1-8 alkylthio group is substituted by one or more halogen atoms which are the same or different, and / or C _1-4 alkyloxy groups which are substituted by one or more halogen atoms which are the same or different. May be);
C _2-8 alkenylthio group (this C _2-8 alkenylthio group is represented by one or more halogen atoms and / or C _1-4 alkyloxy groups substituted by one or more halogen atoms. Optionally substituted);
A C _1-8 alkylsulfinyl group (this C _1-8 alkylsulfinyl group is represented by one or more halogen atoms which are the same or different and / or a C _1-4 alkyloxy group which is substituted by one or more halogen atoms which are the same or different. Optionally substituted);
A C _2-8 alkenylsulfinyl group (this C _2-8 alkenylsulfinyl group is represented by one or more halogen atoms, and / or a C _1-4 alkyloxy group substituted by one or more halogen atoms. Optionally substituted);
C _1-8 alkylsulfonyl group (this C _1-8 alkylsulfonyl group is the same or different one or more halogen atoms, and / or C _1-4 alkyloxy group substituted by one or more same or different halogen atoms. Optionally substituted);
C _2-8 alkenylsulfonyl group (this C _2-8 alkenylsulfonyl group is the same or different one or more halogen atoms and / or C _1-4 alkyloxy group substituted by one or more same or different halogen atoms. Optionally substituted);
Phenyl group (this phenyl group is one or more halogen atoms that are the same or different, a C _1-4 alkyl group that is substituted by one or more halogen atoms that are the same or different, or a C group that is substituted by one or more halogen atoms that are the same or different; _{And a} phenoxy group (this phenoxy group is one or more halogen atoms which are the same or different, and one or more C _1-4 substituted with one or more halogen atoms which are the same or different). An alkyl group, or a group selected from the group consisting of C _1-4 alkyloxy groups substituted by one or more halogen atoms, which are the same or different,
B represents a group selected from the group consisting of a halogen atom, a C _1-4 alkyl group, a C _1-4 alkyloxy group, a nitro group, and a cyano group;
Alternatively, Y ₁ , Y ₂ , Y ₃ , Y ₄ , and Y ₅ are a combination of two adjacent groups,
The halogen atom may be substituted _{-O- (CH} 2) n _-O-,
May be substituted by a halogen atom _{- (CH} 2) n -O-,
The halogen atom may be substituted _{-S- (CH} 2) n _-S-,
May be substituted by a halogen atom _{- (CH} 2) n -S-, or it may be substituted by a halogen atom - _{(CH 2) n} - may represent,
Here, n represents 1, 2 or 3,
Z represents a bond, an oxygen atom, a sulfur atom, SO, SO ₂ , —Q—, —O—Q—, —O—Q—O—, or CO;
Q is a C _1-4 alkylene group (this C _1-4 alkylene group may be substituted with a halogen atom, a cyano group, or a C _1-4 alkyl group which may be substituted with a halogen atom), — (CH ₂ ) _p —CR ₁₀ R ₁₁ — (CH ₂ ) _q — (R ₁₀ and R ₁₁ are taken together, together with the carbon atom to which they are bonded, a halogen atom or an optionally substituted C ₁ atom. Represents a C _3-6 cycloalkyl group which may be substituted with a _-4 alkyl group, and p and q each independently represents an integer of 0 to 3, or a C _2-4 alkenylene group (this C _{2- 4-} alkenylene group represents a halogen atom, a cyano group, or a C _1-4 alkyl group which may be substituted with a halogen atom. ]
Or a horticulturally acceptable salt thereof and at least one other pesticidal agent as an active ingredient.

  According to the present invention, it is possible to efficiently kill pests and protect useful plants by the synergistic effect produced by the combination of the compound represented by the formula (I) and other pest control agents. It becomes.

Detailed description of the invention

Compound of Formula (I) In the present specification, “halogen” means fluorine, chlorine, bromine or iodine, preferably a fluorine atom or a chlorine atom.

The “alkali metal” represented by R ₁ includes sodium or potassium, and the “alkaline earth metal” includes calcium or magnesium.

The C _1-18 alkyl group represented by R ₁ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ or R ₈ may be either linear or branched, preferably C _1-10 alkyl. Group, more preferably a C _1-4 alkyl group. Here, the C _1-18 alkyl group may be substituted, and _{examples of} the substituent include a halogen atom, a C _1-4 alkyloxy group, a C _1-4 alkyloxy-C _1-4 alkyloxy group, C _1-4 alkyloxycarbonyl group, nitro group, cyano group, formyl group, trifluoromethoxy group, acetyl group, acetyloxy group, or C _3-6 cycloalkyl group optionally substituted by a halogen atom is exemplified. Preferably substituted by a halogen atom, a C _1-4 alkyloxy group, a C _1-4 alkyloxy-C _1-4 alkyloxy group, a C _1-4 alkyloxycarbonyl group, a cyano group, an acetyloxy group, or a halogen atom A C _3-6 cycloalkyl group which may be _substituted . The substituent for R ₁ is more preferably a C _1-4 alkyloxy-C _1-4 alkyloxy group or a C _1-4 alkyloxycarbonyl group. The substituent in R ₃ is more preferably a halogen atom or an acetyloxy group. The substituent in R ₄ is more preferably a C _1-4 alkyloxy group or an acetyloxy group. The substituent for R ₅ is more preferably a halogen atom or a C _1-4 alkyloxy group. The substituent in R ₆ , R ₇ or R ₈ is more preferably a halogen atom, a C _1-4 alkyloxy group, or an acetyloxy group.

Specific examples of the C _1-18 alkyl group represented by R ₁ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ or R ₈ include a methyl group, ethyl group, propyl group, i-propyl group, n- Butyl group, i-butyl group, s-butyl group, t-butyl group, n-pentyl group, (2- or 3-methyl) butyl group, 2,3-dimethylpropyl group, n-hexyl group, (2, 3 or 4-methyl) pentyl group, (2,3-, 2,4- or 3,4-dimethyl) butyl group, 2,3,4-trimethylpropyl group, n-heptyl group, n-octyl group, nonyl Group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, chloromethyl group, trichloromethyl group, trifluoromethyl group, (1- or 2-) group Roethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 2-trifluoromethoxyethyl, cyanomethyl, 2-cyanoethyl, cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, 1-methylcyclopropylmethyl group, 2- (1-methylcyclopropyl) ethyl group, 3- (1-methylcyclopropyl) propyl group, 2,2-dimethylcyclopropylmethyl group, 2- (2,2-dimethyl) Cyclopropyl) ethyl group, 3- (2,2-dimethylcyclopropyl) propyl group, 2,2-dichlorocyclopropylmethyl group, 2- (2,2-dichlorocyclopropyl) ethyl group, 3- (2,2 -Dichlorocyclopropyl) propyl group, 2,2-difluorocyclopropylmethyl group, 2- (2,2- A difluorocyclopropyl) ethyl group or a 3- (2,2-difluorocyclopropyl) propyl group may be mentioned.

The C _1-4 alkyl group represented by R ₂ may be linear or branched. Here, this _C1-4 alkyl group may be substituted, and examples of the substituent include a halogen atom, a _C1-4 alkyloxy group, a nitro group, a cyano group, a formyl group, a trifluoromethoxy group, an acetyl group. Group, an acetyloxy group, or a C _3-6 cycloalkyl group which may be substituted with a halogen atom, and preferably a halogen atom or a cyano group.

Specific examples of the C _1-4 alkyl group represented by R ₂ include methyl group, ethyl group, propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, Chloromethyl group, trichloromethyl group, trifluoromethyl group, (1- or 2-) chloroethyl group, 2,2,2-trifluoroethyl group, pentafluoroethyl group, 2-trifluoromethoxyethyl group, cyanomethyl group, Or a 2-cyanoethyl group is mentioned.

The C _2-18 alkenyl group represented by R ₁ , R ₄ , R ₅ or R ₈ may be linear or branched, preferably a C _2-10 alkenyl group, more preferably C _{2. It is a -4} alkenyl group. Here, the C _2-18 alkenyl group may be substituted, and _{examples of} the substituent include a halogen atom, a C _1-4 alkyloxy group, a nitro group, a cyano group, a formyl group, a trifluoromethoxy group, and an acetyl group. , An acetyloxy group, or a C _3-6 cycloalkyl group optionally substituted by a halogen atom. The substituent in R ₄ or R ₅ is preferably a halogen atom, a C _1-4 alkyloxy group, a nitro group, a cyano group, a formyl group, a trifluoromethoxy group, an acetyl group, or an acetyloxy group. A more preferred substituent for R ₁ , R ₄ , R ₅ or R ₈ is a halogen atom.

Specific examples of the C _2-18 alkenyl group represented by R ₁ , R ₄ , R ₅ or R ₈ include a vinyl group, a (1- or 2-) propenyl group, and a (1-, 2- or 3-) butenyl group. , (1-, 2-, 3- or 4-) pentenyl group, (1-, 2-, 3-, 4- or 5-) hexenyl group, (1-, 2-, 3-, 4-, 5) -Or 6-) heptenyl group, (1-, 2-, 3-, 4-, 5-, 6- or 7-) octenyl group, (1-, 2-, 3-, 4-, 5-, 6 -, 7- or 8-) nonenyl group, (1-, 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-) decenyl group, (1-, 2-3, -, 4-, 5-, 6-, 7-, 8-, 9- or 10-) undecenyl group, (1-, 2-, 3-, 4-, 5-, 6-, 7-, 8- , 9-, 10- or 11-) dode Nyl group, (1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10-, 11- or 12-) tridecenyl group, (1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10-, 11-, 12- or 13-) tetradecenyl group, (1-, 2-, 3-, 4--5 -, 6-, 7-, 8-, 9-, 10-, 11-, 12, 13- or 14-) pentadecenyl group, (1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10-, 11-, 12-, 13-, 14- or 15-) hexadecenyl group, (1-, 2-, 3-, 4-, 5-, 6-, 7 -, 8-, 9-, 10-, 11-, 12-, 13-, 14-, 15- or 16-) heptadecenyl group, (1-, 2-, 3-, 4-, 5-, 6- , 7-, 8-, 9-, 10-, 11- 12-, 13-, 14-, 15-, 16- or 17-) octadecenyl group, 1-methylvinyl group, 1-methyl-1-propenyl group, 2-methyl-1-propenyl group, 1,2-dimethyl -1-propenyl group, 1-methyl-1-butenyl group, 1-methyl-2-butenyl group, 2-fluorovinyl group, 2-chlorovinyl group, 2,2-difluorovinyl group, 2,2-dichlorovinyl Group, or 2-trifluoromethoxyvinyl group.

The C _2-4 alkenyl group represented by R ₃ may be linear or branched. Here, the C _2-4 alkenyl group may be substituted, and examples of the substituent include a halogen atom, a C _1-4 alkyloxy group, a nitro group, a cyano group, a formyl group, a trifluoromethoxy group, and an acetyl group. , An acetyloxy group, or a C _3-6 cycloalkyl group optionally substituted with a halogen atom, preferably a halogen atom.

The C _2-18 alkynyl group represented by R ₁ , R ₄ , R ₅ or R ₈ may be either linear or branched, preferably a C _2-10 alkynyl group, more preferably C _{2. -4} alkynyl group. Here, the C _2-18 alkynyl group may be substituted, and _{examples of} the substituent include a halogen atom, a C _1-4 alkyloxy group, a nitro group, a cyano group, a formyl group, a trifluoromethoxy group, and an acetyl group. , An acetyloxy group, or a C _3-6 cycloalkyl group optionally substituted by a halogen atom.

Specific examples of the C _2-18 alkynyl group represented by R ₁ , R ₄ , R ₅ or R ₈ include an ethynyl group, a (1- or 2-) propynyl group, and a (1-, 2- or 3-) butynyl group. , (1-, 2-, 3- or 4-) pentynyl group, (1-, 2-, 3-, 4- or 5-) hexynyl group, (1-, 2-, 3-, 4-, 5) -Or 6-) heptynyl group, (1-, 2-, 3-, 4-, 5-, 6- or 7-) octynyl group, (1-, 2-, 3-, 4-, 5-, 6 -, 7- or 8-) noninyl group, (1-, 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-) decynyl group, (1-, 2-3, -, 4-, 5-, 6-, 7-, 8-, 9- or 10-) undecynyl group, (1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-- , 9-, 10- or 11-) Sinyl group, (1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10-, 11- or 12-) tridecynyl group, (1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10-, 11-, 12- or 13-) tetradecynyl group, (1-, 2-, 3-, 4--5 -, 6-, 7-, 8-, 9-, 10-, 11-, 12-, 13- or 14-) pentadecynyl group, (1-, 2-, 3-, 4-, 5-, 6- , 7-, 8-, 9-, 10-, 11-, 12-, 13-, 14- or 15-) hexadecynyl group, (1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10-, 11-, 12-, 13-, 14-, 15- or 16-) heptadecinyl group, or (1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10 , 11, 12, 13, 14, 15, and a 16 or 17-) octadecynyl group.

The C _3-10 cycloalkyl group represented by R ₁ , R ₄ , R ₅ or R ₈ is preferably a C _3-6 cycloalkyl group. Here, this C _3-10 cycloalkyl may be substituted, and _{examples of} the substituent include a halogen atom, C _1-4 alkyloxy group, nitro group, cyano group, formyl group, trifluoromethyl group, trifluoro group. Examples thereof include a methoxy group, an acetyl group, an acetyloxy group, a C _1-4 alkyl group, or a C _3-6 cycloalkyl group optionally substituted by a halogen atom, preferably a halogen atom or a C _1-4 alkyl group. is there.

Specific examples of the C _3-10 cycloalkyl group represented by R ₁ , R ₄ , R ₅ or R ₈ include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, Cyclodecyl group, 1-methylcyclopropyl group, 2-methylcyclopropyl group, 1-methyl-2-ethylcyclopropyl group, 2-chlorocyclopropyl group, 2-fluorocyclopropyl group, 2,2-dimethylcyclopropyl group 2,2-dichlorocyclopropyl group, 2,2-difluorocyclopropyl group, 1-methyl-2-chlorocyclopropyl group, 1-methyl-2-fluorocyclopropyl group, 1-methyl-2,2-dimethyl Cyclopropyl group, 1-methyl-2,2-dichlorocyclopropyl group, 1-methyl-2,2 Difluorocyclopropyl group, 1-methylcyclobutyl group, 2-methylcyclobutyl group, 2-chlorocyclobutyl group, 2-fluorocyclobutyl group, 2,2-dimethylcyclobutyl group, 2,2-dichlorocyclobutyl group 2,2-difluorocyclobutyl group, 1-methylcyclopentyl group, 2-methylcyclopentyl group, 3-methylcyclopentyl group, 3-chlorocyclopentyl group, 3-fluorocyclopentyl group, 3,3-dimethylcyclopentyl group, 3, Examples include 3-dichlorocyclopentyl group, 3,3-difluorocyclopentyl group, 1-methylcyclohexyl group, and 2,2-dimethylcyclohexyl group.

The phenyl lower alkyl group represented by R ₁ , R ₄ , R ₅ or R ₈ is preferably a C _1-4 alkyl group having a phenyl group. Here, the phenyl group in the phenyl lower alkyl group may be substituted, and examples of the substituent include a halogen atom, a C _1-4 alkyl group, a C _1-4 alkyloxy group, a nitro group, a cyano group, and a formyl group. , A trifluoromethyl group, a trifluoromethoxy group, an acetyl group, an acetyloxy group, or a C _3-6 cycloalkyl group optionally substituted by a halogen atom.

Specific examples of the phenyl lower alkyl group represented by R ₁ , R ₄ , R ₅ or R ₈ include a benzyl group, (1- or 2-) phenylethyl group, (1-, 2- or 3-) phenylpropyl group. , (1-, 2-, 3- or 4-) phenylbutyl group.

The phenoxy lower alkyl group represented by R ₁ , R ₄ , R ₅ or R ₈ is preferably a C _1-4 alkyl group having a phenoxy group. Here, the phenyl group in the phenoxy lower alkyl group may be substituted, and examples of the substituent include a halogen atom, a C _1-4 alkyl group, a C _1-4 alkyloxy group, a nitro group, a cyano group, and a formyl group. , A trifluoromethyl group, a trifluoromethoxy group, an acetyl group, an acetyloxy group, or a C _3-6 cycloalkyl group optionally substituted by a halogen atom.

Specific examples of the phenoxy lower alkyl group represented by R ₁ , R ₄ , R ₅ or R ₈ include a phenoxymethyl group, a (1- or 2-) phenoxyethyl group, and a (1-, 2- or 3-) phenoxypropyl. Group, (1-, 2-, 3- or 4-) phenoxybutyl group. Here, the phenyl group may be substituted, and preferred substituents include a halogen atom, a C _1-4 alkyl group, a C _1-4 alkyloxy group, a nitro group, a cyano group, a formyl group, and trifluoro. A methoxy group, an acetyl group, or an acetyloxy group is mentioned.

The phenyl group represented by R ₁ , R ₄ , R ₅ , R ₆ , R ₇ or R ₈ may be substituted, and preferred substituents include a halogen atom, a C _1-4 alkyl group, and C _1-4. Examples thereof include an alkyloxy group, a nitro group, a cyano group, a formyl group, a trifluoromethyl group, a trifluoromethoxy group, an acetyl group, an acetyloxy group, or a C _3-6 cycloalkyl group which may be substituted with a halogen atom. .

The heterocyclic group represented by R ₁ , R ₄ , R ₅ or R ₈ is preferably a 5- or 6-membered heterosaturated or aromatic ring containing one S, O or N as a hetero atom, and two N as a hetero atom A 5- or 6-membered heterosaturated or aromatic ring, O or S as a heteroatom, and a 5- or 6-membered heterosaturated or aromatic ring containing one N, more preferably a thienyl group, a furyl group, or a pyrrolyl group , An imidazolyl group, a pyrazolyl group, an isothiazolyl group, an isoxazolyl group, a thiazolyl group, an oxazolyl group, a pyridyl group, and a pyrimidinyl group. Here, this heterocyclic group may be substituted, and examples of the substituent include a halogen atom, a C _1-4 alkyl group, a C _1-4 alkyloxy group, a nitro group, a cyano group, a formyl group, and a trifluoromethyl group. , A trifluoromethoxy group, an acetyl group, an acetyloxy group, or a C _3-6 cycloalkyl group optionally substituted by a halogen atom.

Specific examples of the heterocyclic group represented by R ₁ , R ₄ , R ₅ or R ₈ include (2- or 3-) thienyl group, (2- or 3-) furyl group, (1-, 2- or 3). -) Pyrrolyl group, (1- or 2-) imidazolyl group, (1-, 3-, 4- or 5-) pyrazolyl group, (3-, 4- or 5-) isothiazolyl group, (3-, 4- Or 5-) isoxazolyl group, (2-, 4- or 5-) thiazolyl group, (2-, 4- or 5-) oxazolyl group, (2-, 3- or 4-) pyridyl group, or (2- , 4-, 5- or 6-) pyrimidinyl group.

The C _1-4 alkylthio group represented by R ₄ may be linear or branched. Here, the C _1-4 alkylthio group may be substituted, and examples of the substituent include a halogen atom, a C _1-4 alkyloxy group, a nitro group, a cyano group, a formyl group, a trifluoromethoxy group, and an acetyl group. , An acetyloxy group, or a C _3-6 cycloalkyl group optionally substituted with a halogen atom, preferably a halogen atom.

The C _1-4 alkoxy group represented by R ₃ may be either linear or branched. Here, the C _1-4 alkoxy group may be substituted, and examples of the substituent include a halogen atom, a C _1-4 alkyloxy group, a nitro group, a cyano group, a formyl group, a trifluoromethoxy group, and an acetyl group. , An acetyloxy group, or a C _3-6 cycloalkyl group optionally substituted with a halogen atom, preferably a halogen atom.

Specific examples of the C _1-4 alkyl group which may be substituted with a halogen atom represented by X ₁ , X ₂ and X ₃ include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, iso -Propyl group, iso-butyl group, s-butyl group, t-butyl group, trifluoromethyl group, trichloromethyl group, difluoromethyl group, dichloromethyl group, trifluoroethyl group, trichloroethyl group, tetrafluoroethyl group, Or a tetrachloroethyl group, preferably a methyl group, an ethyl group, a trifluoromethyl group, a trichloromethyl group, a difluoromethyl group, a dichloromethyl group, a trifluoroethyl group, a trichloroethyl group, a pentafluoroethyl group, or a pentachloro group. An ethyl group, more preferably a methyl group, an ethyl group, or a trifluoromethyl group. Is a group or difluoromethyl group,.

Specific examples of the C _1-4 alkyloxy group which may be substituted with a halogen atom represented by X ₁ , X ₂ and X ₃ include a methoxy group, an ethoxy group, an n-propyloxy group and an n-butyloxy group. , Iso-propyloxy group, iso-butyloxy group, s-butyloxy group, t-butyloxy group, trifluoromethoxy group, trichloromethoxy group, difluoromethoxy group, dichloromethoxy group, trifluoroethoxy group, trichloroethoxy group, pentafluoro An ethoxy group or a pentachloroethoxy group is preferable, and a methoxy group, an ethoxy group, a trifluoromethoxy group, a trichloromethoxy group, a difluoromethoxy group, a dichloromethoxy group, a trifluoroethoxy group, a trichloroethoxy group, or a pentafluoroethoxy group is preferable. , Ma Is a penta-chloroethoxy groups, more preferably methoxy group, an ethoxy group, a trifluoromethoxy group or a difluoromethoxy group,.

Specific examples of the C _1-4 alkylthio group which may be substituted with a halogen atom represented by X ₁ , X ₂ and X ₃ include a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an iso -Propylthio group, iso-butylthio group, s-butylthio group, t-butylthio group, trifluoromethylthio group, trichloromethylthio group, difluoromethylthio group, dichloromethylthio group, trifluoroethylthio group, trichloroethylthio group, pentafluoroethyl A thio group or a pentachloroethylthio group, preferably a methylthio group, an ethylthio group, a trifluoromethylthio group, a trichloromethylthio group, a difluoromethylthio group, a dichloromethylthio group, a trifluoroethylthio group, a trichloroethylthio group, a tetra A Ruoroechiruchio group or tetra chloroethyl thio group, more preferably a methylthio group, an ethylthio group, a trifluoromethylthio group or difluoromethyl thio group.

Specific examples of the C _1-4 alkyloxycarbonyl group which may be substituted by a halogen atom represented by X ₁ , X ₂ and X ₃ include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propyloxycarbonyl group, n-butyloxycarbonyl group, iso-propyloxycarbonyl group, iso-butyloxycarbonyl group, s-butyloxycarbonyl group, t-butyloxycarbonyl group, trifluoromethoxycarbonyl group, trichloromethoxycarbonyl group, difluoromethoxycarbonyl group , Dichloromethoxycarbonyl group, trifluoroethoxycarbonyl group, trichloroethoxycarbonyl group, tetrafluoroethoxycarbonyl group, tetrachloroethoxycarbonyl group, pentafluoroethoxycarbonyl group, or An chlorochlorocarbonyl group, preferably a methoxycarbonyl group, an ethoxycarbonyl group, a trifluoromethoxycarbonyl group, a trichloromethoxycarbonyl group, a difluoromethoxycarbonyl group, a dichloromethoxycarbonyl group, a trifluoroethoxycarbonyl group, a trichloroethoxycarbonyl group. , A pentafluoroethoxycarbonyl group, or a pentachloroethoxycarbonyl group, more preferably a methoxycarbonyl group, an ethoxycarbonyl group, a trifluoromethoxycarbonyl group, or a difluoromethoxycarbonyl group.

W ₁ , W ₂ , and W ₃ are preferably CY ₁ , CY ₂ , and CY ₃ , respectively.

The C _1-8 alkyl group represented by Y ₁ , Y ₂ , Y ₃ , Y ₄ , and Y ₅ is the same or different one or more halogen atoms, and C _1-4 substituted with the same or different one or more halogen atoms. It is substituted by one or more groups selected from an alkyloxy group and a C _2-4 alkenyloxy group substituted by one or more halogen atoms which are the same or different. The C _1-8 alkyl group is preferably substituted with one or more halogen atoms that are the same or different and / or a C _1-4 alkyloxy group that is substituted with one or more halogen atoms that are the same or different. More preferably, it is substituted with one or more halogen atoms which are the same or different. Specific examples of the C _1-8 alkyl group include a chloromethyl group, a (1- or 2-) chloroethyl group, a (1-, 2- or 3-) chloro-n-propyl group, (1-2, -, 3- or 4-) chloro-n-butyl group, (1-, 2-, 3-, 4- or 5-) chloro-n-pentyl group, (1-, 2-, 3-, 4- , 5- or 6-) chloro-n-hexyl group, (1-, 2-, 3-, 4-, 5-, 6- or 7-) chloro-n-heptyl group, (1-, 2-, 3-, 4-, 5-, 6-, 7- or 8-) chloro-n-octyl group, fluoromethyl group, (1- or 2-) fluoroethyl group, (1-, 2- or 3-) Fluoro-n-propyl group, (1-, 2-, 3- or 4-) fluoro-n-butyl group, (1-, 2-, 3-, 4- or 5-) full Oro-n-pentyl group, (1-, 2-, 3-, 4-, 5- or 6-) fluoro-n-hexyl group, (1-, 2-, 3-, 4-, 5-, 6 -Or 7-) fluoro-n-heptyl group, (1-, 2-, 3-, 4-, 5-, 6-, 7- or 8-) fluoro-n-octyl group, dichloromethyl group, difluoromethyl Group, trichloromethyl group, trifluoromethyl group, trichloroethyl group, trifluoroethyl group, pentachloroethyl group, pentafluoroethyl group, 3,3,3-trichloropropyl group, 3,3,3-trifluoropropyl group 2,2,3,3-tetrachloropropyl group, 2,2,3,3-tetrafluoropropyl group, ditrifluoromethylmethyl group, 2,2-ditrifluoromethylethyl group, heptafluoro-iso-propyl group Nonafluoro-iso-butyl group, chloromethoxymethyl group, (1- or 2-) chloromethoxyethyl group, (1-, 2- or 3-) chloromethoxy-n-propyl group, (1-, 2-3, -Or 4-) chloromethoxy-n-butyl group, (1-, 2-, 3-, 4- or 5-) chloromethoxy-n-pentyl group, (1-, 2-, 3-, 4-, 5- or 6-) chloromethoxy-n-hexyl group, (1-, 2-, 3-, 4-, 5-, 6- or 7-) chloromethoxy-n-heptyl group, (1-, 2- , 3-, 4-, 5-, 6-, 7- or 8-) chloromethoxy-n-octyl group, fluoromethoxymethyl group, (1- or 2-) fluoromethoxyethyl group, (1-, 2- Or 3-) fluoromethoxy-n-propyl group, (1-, 2-, -Or 4-) fluoromethoxy-n-butyl group, (1-, 2-, 3-, 4- or 5-) fluoromethoxy-n-pentyl group, (1-, 2-, 3-, 4-, 5- or 6-) fluoromethoxy-n-hexyl group, (1-, 2-, 3-, 4-, 5-, 6- or 7-) fluoromethoxy-n-heptyl group, (1-, 2- , 3-, 4-, 5-, 6-, 7- or 8-) fluoromethoxy-n-octyl group, dichloromethoxymethyl group, difluoromethoxymethyl group, trichloromethoxymethyl group, trifluoromethoxymethyl group, trichloromethoxy Ethyl group, trifluoromethoxyethyl group, pentachloroethoxymethyl group, pentafluoroethoxymethyl group, pentachloroethoxyethyl group, pentafluoroethoxyethyl group, 3, 3, 3 -Trichloropropyloxymethyl group, 3,3,3-trifluoropropyloxymethyl group, 3,3,3-trichloropropyloxyethyl group, 3,3,3-trifluoropropyloxyethyl group, 2,2,3 , 3-tetrachloropropyloxymethyl group, 2,2,3,3-tetrafluoropropyloxymethyl group, or trifluoromethoxy-1,1,2-trifluoroethyl group, preferably chloromethyl group, (1- or 2-) chloroethyl group, (1-, 2- or 3-) chloro-n-propyl group, fluoromethyl group, (1- or 2-) fluoroethyl group, (1-, 2- or 3 -) Fluoro-n-propyl group, dichloromethyl group, difluoromethyl group, trichloromethyl group, trifluoromethyl group, trichloroethyl group Trifluoroethyl group, pentachloroethyl group, pentafluoroethyl group, 3,3,3-trichloropropyl group, 3,3,3-trifluoropropyl group, 2,2,3,3-tetrachloropropyl group, 2 , 2,3,3-tetrafluoropropyl group, ditrifluoromethylmethyl group, 2,2-ditrifluoromethylethyl group, heptafluoro-iso-propyl group, chloromethoxymethyl group, (1- or 2-) chloromethoxy Ethyl group, (1-, 2- or 3-) chloromethoxy-n-propyl group, (1-, 2-, 3- or 4-) chloromethoxy-n-butyl group, fluoromethoxymethyl group, (1- Or 2-) fluoromethoxyethyl group, (1-, 2- or 3-) fluoromethoxy-n-propyl group, (1-, 2-, 3- or 4-) Fluoromethoxy-n-butyl group, dichloromethoxymethyl group, difluoromethoxymethyl group, trichloromethoxymethyl group, trifluoromethoxymethyl group, trichloromethoxyethyl group, trifluoromethoxyethyl group, pentachloroethoxymethyl group, pentafluoroethoxymethyl group , Pentachloroethoxyethyl group, pentafluoroethoxyethyl group, 3,3,3-trichloropropyloxymethyl group, 3,3,3-trifluoropropyloxymethyl group, 3,3,3-trichloropropyloxyethyl group, 3,3,3-trifluoropropyloxyethyl group, 2,2,3,3-tetrachloropropyloxymethyl group, 2,2,3,3-tetrafluoropropyloxymethyl group, or trifluoromethoxy-1, 1,2-Triflu Oroethyl group, more preferably trifluoromethyl group, trifluoroethyl group, tetrafluoroethyl group, 3,3,3-trifluoropropyl group, 2,2,3,3-tetrafluoropropyl group, difluoromethoxymethyl Group, trifluoromethoxymethyl group, trifluoromethoxyethyl group, pentafluoroethoxymethyl group, pentafluoroethoxyethyl group, 3,3,3-trifluoropropyloxymethyl group, 3,3,3-trifluoropropyloxyethyl Group, 2,2,3,3-tetrafluoropropyloxymethyl group, or trifluoromethoxy-1,1,2-trifluoroethyl group.

The C _2-8 alkenyl group represented by Y ₁ , Y ₂ , Y ₃ , Y ₄ and Y ₅ is the same or different one or more halogen atoms, and C ₁ -substituted by one or more halogen atoms. ₄ alkyloxy groups, and one or more halogen atoms substituted by one or more groups selected from the same or different C _2-4 alkenyloxy groups substituted by one or more halogen atoms, preferably the same or different one or more halogens It is substituted by an atom. Specific examples of the C _2-8 alkenyl group include a 2-chloro-3,3,3-trifluoro-1-propenyl group.

The C _1-8 alkyloxy group represented by Y ₁ , Y ₂ , Y ₃ , Y ₄ and Y ₅ is the same or different one or more halogen atoms, and C ₁ -substituted by one or more halogen atoms. ₄ alkyl group, and those substituted with one or more groups selected from C _2-4 alkenyloxy group substituted by the same or different one or more halogen atoms. The C _1-8 alkyloxy group is preferably one substituted with one or more halogen atoms which are the same or different and / or a C _1-4 alkyloxy group substituted with one or more halogen atoms which are the same or different. is there. According to one embodiment, the C _1-8 alkyloxy group is substituted by one or more halogen atoms which are the same or different. Specific examples of the C _1-8 alkyloxy group include a chloromethyloxy group, a (1- or 2-) chloroethyloxy group, a (1-, 2- or 3-) chloro-n-propyloxy group, ( 1-, 2-, 3- or 4-) chloro-n-butyloxy group, (1-, 2-, 3-, 4- or 5-) chloro-n-pentyloxy group, (1-, 2-, 3-, 4-, 5- or 6-) chloro-n-hexyloxy group, (1-, 2-, 3-, 4-, 5-, 6- or 7-) chloro-n-heptyloxy group, (1-, 2-, 3-, 4-, 5-, 6-, 7- or 8-) chloro-n-octyloxy group, fluoromethyloxy group, (1- or 2-) fluoroethyloxy group, (1-, 2- or 3-) fluoro-n-propyloxy group, (1-, 2-, 3- or 4-) fluoro-n-butyloxy group, (1-, 2-, 3-, 4- or 5-) fluoro-n-pentyloxy group, (1-, 2-, 3-, 4-, 5- or 6-) fluoro-n-hexyloxy group, (1-, 2-, 3-, 4-, 5-, 6- or 7-) fluoro-n-heptyloxy group, (1-, 2-, 3- 4-, 5-, 6-, 7- or 8-) fluoro-n-octyloxy group, dichloromethyloxy group, difluoromethyloxy group, trichloromethyloxy group, trifluoromethyloxy group, trichloroethyloxy group, Trifluoroethyloxy group, pentachloroethyloxy group, pentafluoroethyloxy group, 3,3,3-trichloropropyloxy group, 3,3,3-trifluoropropyloxy group, 2,2,3,3-tetrac Ropropyloxy group, 2,2,3,3-tetrafluoropropyloxy group, ditrifluoromethylmethyloxy group, 2,2-ditrifluoromethylethyloxy group, heptafluoro-iso-propyloxy group, nonafluoro-iso- Butyloxy group, chloromethoxymethoxy group, (1- or 2-) chloromethoxymethoxy group, (1-, 2- or 3-) chloromethoxy-n-propyloxy group, (1-, 2-, 3- or 4 -) Chloromethoxy-n-butyloxy group, (1-, 2-, 3-, 4- or 5-) chloromethoxy-n-pentyloxy group, (1-, 2-, 3-, 4-, 5- Or 6) chloromethoxy-n-hexyloxy group, (1-, 2-, 3-, 4-, 5-, 6- or 7-) chloromethoxy-n-heptyloxy group (1-, 2-, 3-, 4-, 5-, 6-, 7- or 8-) chloromethoxy-n-octyloxy group, fluoromethoxymethoxy group, (1- or 2-) fluoromethoxyethoxy group , (1-, 2- or 3-) fluoromethoxy-n-propyloxy group, (1-, 2-, 3- or 4-) fluoromethoxy-n-butyloxy group, (1-, 2-, 3- , 4- or 5-) fluoromethoxy-n-pentyloxy group, (1-, 2-, 3-, 4-, 5- or 6-) fluoromethoxy-n-hexyloxy group, (1-, 2- , 3-, 4-, 5-, 6- or 7-) fluoromethoxy-n-heptyloxy group, (1-, 2-, 3-, 4-, 5-, 6-, 7- or 8-) Fluoromethoxy-n-octyloxy group, dichloromethoxymethoxy group, Difluoromethoxymethoxy group, trichloromethoxymethoxy group, trifluoromethoxymethoxy group, trichloromethoxyethoxy group, trifluoromethoxyethoxy group, pentachloroethoxymethoxy group, pentafluoroethoxymethoxy group, pentachloroethoxyethoxy group, pentafluoroethoxyethoxy group 3,3,3-trichloropropyloxymethoxy group, 3,3,3-trifluoropropyloxymethoxy group, 3,3,3-trichloropropyloxyethoxy group, 3,3,3-trifluoropropyloxyethoxy group 2,2,3,3-tetrachloropropyloxymethoxy group, 2,2,3,3-tetrafluoropropyloxymethoxy group, 1,1,2,2,3,3,3-heptafluoropropyloxy- 1,2,2-tri Fluoroethoxy group, 1,1,2,2,3,3,3-heptafluoropropyloxy-1,1,2-trifluoroethoxy group, or trifluoromethoxy-1,1,2-trifluoroethoxy group Preferably a chloromethyloxy group, a (1- or 2-) chloroethyloxy group, a (1-, 2- or 3-) chloro-n-propyloxy group, a fluoromethyloxy group, (1- or 2- ) Fluoroethyloxy group, (1-, 2- or 3-) fluoro-n-propyloxy group, dichloromethyloxy group, difluoromethyloxy group, trichloromethyloxy group, trifluoromethyloxy group, trichloroethyloxy group, Trifluoroethyloxy group, pentachloroethyloxy group, pentafluoroethyloxy group, 3,3,3-to Chloropropyloxy group, 3,3,3-trifluoropropyloxy group, 2,2,3,3-tetrachloropropyloxy group, 2,2,3,3-tetrafluoropropyloxy group, ditrifluoromethylmethyloxy Group, 2,2-ditrifluoromethylethyloxy group, heptafluoro-iso-propyloxy group, chloromethoxymethoxy group, (1- or 2-) chloromethoxyethoxy group, (1-, 2- or 3-) chloro Methoxy-n-propyloxy group, (1-, 2-, 3- or 4-) chloromethoxy-n-butyloxy group, fluoromethoxymethoxy group, (1- or 2-) fluoromethoxyethoxy group, (1-, 2- or 3-) fluoromethoxy-n-propyloxy group, (1-, 2-, 3- or 4-) fluoromethoxy- n-butyloxy group, dichloromethoxymethoxy group, difluoromethoxymethoxy group, trichloromethoxymethoxy group, trifluoromethoxymethoxy group, trichloromethoxyethoxy group, trifluoromethoxyethoxy group, pentachloroethoxymethoxy group, pentafluoroethoxymethoxy group, penta Chloroethoxyethoxy group, pentafluoroethoxyethoxy group, 3,3,3-trichloropropyloxymethoxy group, 3,3,3-trifluoropropyloxymethoxy group, 3,3,3-trichloropropyloxyethoxy group, 3, 3,3-trifluoropropyloxyethoxy group, 2,2,3,3-tetrachloropropyloxymethoxy group, 2,2,3,3-tetrafluoropropyloxymethoxy group, 1,1,2,2,3 , 3, 3 Heptafluoropropyloxy-1,2,2-trifluoroethoxy group, 1,1,2,2,3,3,3-heptafluoropropyloxy-1,1,2-trifluoroethoxy group, or trifluoromethoxy -1,1,2-trifluoroethoxy group, more preferably trifluoromethyloxy group, trifluoroethyloxy group, pentafluoroethyloxy group, 3,3,3-trifluoropropyloxy group, 2,2 , 3,3-tetrafluoropropyloxy group, difluoromethoxymethoxy group, trifluoromethoxymethoxy group, trifluoromethoxyethoxy group, pentafluoroethoxymethoxy group, pentafluoroethoxyethoxy group, 3,3,3-trifluoropropyloxy Methoxy group, 3,3,3-trifluoropropyl Xyloxy group, 2,2,3,3-tetrafluoropropyloxymethoxy group, 1,1,2,2,3,3,3-heptafluoropropyloxy-1,2,2-trifluoroethoxy group, 1, 1,2,2,3,3,3-heptafluoropropyloxy-1,1,2-trifluoroethoxy group or trifluoromethoxy-1,1,2-trifluoroethoxy group.

The C _2-8 alkenyloxy group represented by Y ₁ , Y ₂ , Y ₃ , Y ₄ and Y ₅ is the same or different one or more halogen atoms, or C ₁ substituted with one or more halogen atoms. Substituted with one or more groups selected from a _-4 alkyloxy group and a _C2-4 alkenyloxy group substituted with one or more halogen atoms, the same or different. Specific examples of the C _2-8 alkenyloxy group include a 3,3-dichloro-2-propenyloxy group and a 3-chloro-4,4,4-trifluoro-2-butenyloxy group.

The C _1-8 alkyloxycarbonyl group represented by Y ₁ , Y ₂ , Y ₃ , Y ₄ , and Y ₅ is substituted with one or more halogen atoms that are the same or different and / or one or more halogen atoms that are the same or different. And _optionally substituted by a C _1-4 alkyloxy group. Specific examples of the C _1-8 alkyloxycarbonyl group include an ethyloxycarbonyl group.

The C _1-8 alkylthio group represented by Y ₁ , Y ₂ , Y ₃ , Y ₄ and Y ₅ is the same or different one or more halogen atoms and / or C substituted with one or more same or different halogen atoms. _It may be substituted with a _1-4 alkyloxy group. The C _1-8 alkylthio group is preferably a C _1-8 alkylthio group substituted by one or more halogen atoms which are the same or different. Specific examples of this C _1-8 alkylthio group include methylthio group, ethylthio group, n-propylthio group, n-butylthio group, iso-propylthio group, iso-butylthio group, s-butylthio group, t-butylthio group, n -Pentylthio group, (2- or 3-methyl) butylthio group, 2,3-dimethylpropylthio group, n-hexylthio group, (2 or 3 or 4-methyl) pentylthio group, (2,3- or 2,4 -Or 3,4-dimethyl) butylthio, 2,3,4-trimethylpropylthio, n-heptylthio, n-octylthio, trifluoromethylthio, trichloromethylthio, difluoromethylthio, dichloromethylthio, tri Fluoroethylthio group, trichloroethylthio group, pentafluoroethylthio group, pen Tachloroethylthio group, chloromethoxymethylthio group, (1- or 2-) chloromethoxyethylthio group, (1-, 2- or 3-) chloromethoxy-n-propylthio group, (1-, 2-3, -Or 4-) chloromethoxy-n-butylthio group, (1-, 2-, 3-, 4- or 5-) chloromethoxy-n-pentylthio group, (1-, 2-, 3-, 4-, 5- or 6-) chloromethoxy-n-hexylthio group, (1-, 2-, 3-, 4-, 5-, 6- or 7-) chloromethoxy-n-heptylthio group, (1-, 2- , 3-, 4-, 5-, 6-, 7- or 8-) chloromethoxy-n-octylthio group, fluoromethoxymethylthio group, (1- or 2-) fluoromethoxyethylthio group, (1--2 -Or 3-) fluoromethoxy-n Propylthio group, (1-, 2-, 3- or 4-) fluoromethoxy-n-butylthio group, (1-, 2-, 3-, 4- or 5-) fluoromethoxy-n-pentylthio group, (1 -, 2-, 3-, 4-, 5- or 6-) fluoromethoxy-n-hexylthio group, (1-, 2-, 3-, 4-, 5-, 6- or 7-) fluoromethoxy- n-heptylthio group, (1-, 2-, 3-, 4-, 5-, 6-, 7- or 8-) fluoromethoxy-n-octylthio group, dichloromethoxymethylthio group, difluoromethoxymethylthio group, trichloromethoxy Methylthio group, trifluoromethoxymethylthio group, trichloromethoxyethylthio group, trifluoromethoxyethylthio group, pentachloroethoxymethylthio group, pentafluoroethoxy Tylthio group, pentachloroethoxyethylthio group, pentafluoroethoxyethylthio group, 3,3,3-trichloropropyloxymethylthio group, 3,3,3-trifluoropropyloxymethylthio group, 3,3,3-trichloropropyl Oxyethylthio group, 3,3,3-trifluoropropyloxyethylthio group, 2,2,3,3-tetrachloropropyloxymethylthio group, 2,2,3,3-tetrafluoropropyloxymethylthio group, or And trifluoromethoxy-1,1,2-trifluoroethylthio group, preferably methylthio group, ethylthio group, trifluoromethylthio group, trichloromethylthio group, difluoromethylthio group, dichloromethylthio group, trifluoroethylthio group, Trichloroethylthio group, tetra Fluoroethylthio group, tetrachloroethylthio group, chloromethoxymethylthio group, (1- or 2-) chloromethoxyethylthio group, (1-, 2- or 3-) chloromethoxy-n-propylthio group, (1--2 -, 3- or 4-) chloromethoxy-n-butylthio group, fluoromethoxymethylthio group, (1- or 2-) fluoromethoxyethylthio group, (1-, 2- or 3-) fluoromethoxy-n-propylthio group Group, (1-, 2-, 3- or 4-) fluoromethoxy-n-butylthio group, dichloromethoxymethylthio group, difluoromethoxymethylthio group, trichloromethoxymethylthio group, trifluoromethoxymethylthio group, trichloromethoxyethylthio group, Trifluoromethoxyethylthio group, pentachloroethoxy Tilthio group, pentafluoroethoxymethylthio group, pentachloroethoxyethylthio group, pentafluoroethoxyethylthio group, 3,3,3-trichloropropyloxymethylthio group, 3,3,3-trifluoropropyloxymethylthio group, 3, 3,3-trichloropropyloxyethylthio group, 3,3,3-trifluoropropyloxyethylthio group, 2,2,3,3-tetrachloropropyloxymethylthio group, 2,2,3,3-tetrafluoro A propyloxymethylthio group or a trifluoromethoxy-1,1,2-trifluoroethylthio group, more preferably a methylthio group, an ethylthio group, a trifluoromethylthio group, a difluoromethylthio group, a difluoromethoxymethylthio group, a trifluoromethoxy group. Methylthio group Trifluoromethoxyethylthio group, pentafluoroethoxymethylthio group, pentafluoroethoxyethylthio group, 3,3,3-trifluoropropyloxymethylthio group, 3,3,3-trifluoropropyloxyethylthio group, 2,2 , 3,3-tetrafluoropropyloxymethylthio group, or trifluoromethoxy-1,1,2-trifluoroethylthio group.

The C _2-8 alkenylthio group represented by Y ₁ , Y ₂ , Y ₃ , Y ₄ , and Y ₅ is substituted with one or more halogen atoms that are the same or different and / or one or more halogen atoms that are the same or different. It may be substituted by a C _1-4 alkyloxy group. Specific examples of the C _2-8 alkenylthio group include a 3,4,4-fluoro-3-butenylthio group and a 3,3-dichloro-2-propenylthio group.

C _1-8 alkylsulfinyl group represented by Y ₁ , Y ₂ , Y ₃ , Y ₄ and Y ₅ is substituted by one or more halogen atoms which are the same or different and / or one or more halogen atoms which are the same or different It may be substituted by a C _1-4 alkyloxy group.

C _2-8 alkenylsulfinyl group represented by Y ₁ , Y ₂ , Y ₃ , Y ₄ , and Y ₅ is substituted with one or more halogen atoms that are the same or different and / or one or more halogen atoms that are the same or different It may be substituted by a C _1-4 alkyloxy group.

C _1-8 alkylsulfonyl group represented by Y ₁ , Y ₂ , Y ₃ , Y ₄ , and Y ₅ is substituted by one or more halogen atoms that are the same or different and / or one or more halogen atoms that are the same or different It may be substituted by a C _1-4 alkyloxy group. The C _1-8 alkylsulfonyl group is preferably substituted by one or more halogen atoms which are the same or different. Specific examples of the C _1-8 alkylsulfonyl group include a trifluoromethylsulfonyl group.

The C _2-8 alkenylsulfonyl group represented by Y ₁ , Y ₂ , Y ₃ , Y ₄ , and Y ₅ is substituted with one or more halogen atoms that are the same or different and / or one or more halogen atoms that are the same or different. It may be substituted by a C _1-4 alkyloxy group.

The phenyl group represented by Y ₁ , Y ₂ , Y ₃ , Y ₄ , and Y ₅ is the same or different one or more halogen atoms, a C _1-4 alkyl group substituted with one or more halogen atoms, or It is substituted by a C _1-4 alkyloxy group substituted by one or more halogen atoms which are the same or different. This phenyl group is preferably substituted with one or more halogen atoms which are the same or different, or a C _1-4 alkyl group substituted with one or more halogen atoms which are the same or different. Specific examples of this phenyl group include 4-trifluoromethyl-phenyl group.

The phenoxy group represented by Y ₁ , Y ₂ , Y ₃ , Y ₄ , and Y ₅ is the same or different one or more halogen atoms, a C _1-4 alkyl group substituted by one or more halogen atoms, Alternatively, it is substituted by a C _1-4 alkyloxy group substituted by one or more halogen atoms which are the same or different. This phenoxy group is preferably substituted by one or more halogen atoms which are the same or different, or a C _1-4 alkyl group substituted by one or more halogen atoms which are the same or different. Specific examples of this phenoxy group include 4-trifluoromethyl-phenoxy group.

Y ₁ , Y ₂ , Y ₃ , Y ₄ , and Y ₅ are each a group of two adjacent groups, which may be substituted with a halogen atom —O— (CH ₂ ) _n —O—, halogen — (CH ₂ ) _n —O— which may be substituted by an atom, —S— (CH ₂ ) _n —S— which may be substituted by a halogen atom, or which may be substituted by a halogen atom— ( CH ₂ ) _n —S— or — (CH ₂ ) _n — which may be substituted by a halogen atom may be represented, and preferably —O— (CH ₂ ) _n which may be substituted by a halogen atom. -O-. Here, n represents 1, 2 or 3, preferably 1 or 2. Specific examples of such groups include —O— (CF ₂ ) ₂ —O—, —O— (CH ₂ ) ₂ —O—, — (CF ₂ ) ₂ —O—, —O— (CF ₂ ) ₂ — (CH ₂ ) —, —S— (CF ₂ ) ₂ —S—, — (CF ₂ ) ₂ —S—, — (CF ₂ ) ₃ — and the like, preferably —O— ( CF ₂₎ it is a ₂ -O-.

Z represents a bond (single bond), an oxygen atom, a sulfur atom, SO, SO ₂ , —Q—, —O—Q—, —O—Q—O—, or CO. Here, Q is a C _1-4 alkylene group (this C _1-4 alkylene group may be substituted with a halogen atom, a cyano group, or a C _1-4 alkyl group which may be substituted with a halogen atom). _{good), - (CH 2) p} -CR 10 R 11 - (CH 2) q - (R 10 and _{R 11} together with the carbon atoms to which they are attached may be substituted with a halogen atom or a halogen atom Represents a C _3-6 cycloalkyl group which may be substituted by a good C _1-4 alkyl group, and p and q each independently represent an integer of 0 to 3, or a C _2-4 alkenylene group (this C _2-4 alkenylene group represents a halogen atom, a cyano group, or a C _1-4 alkyl group optionally substituted by a halogen atom), preferably C _1-4 alkylene group (this C _1-4 alkylene group may be substituted by a C _1-4 alkyl group which may be substituted by a halogen atom, a cyano group or a halogen atom). Specific examples of Q include a methylene group, an ethylene group, a propylene group, and a 2,2-dimethylpropylene group. When Z represents a bond (single bond), in the formula (I), the two ring parts are directly bonded (without any atoms interposed). Z preferably represents a bond (single bond), an oxygen atom, a sulfur atom, SO, SO ₂ , CH ₂ , OCH ₂ , O (CH ₂ ) ₃ O, or CO, more preferably an oxygen atom, a sulfur atom, It represents SO, SO ₂ , CH ₂ , OCH ₂ , or CO, more preferably an oxygen atom, OCH ₂ , or O (CH ₂ ) ₃ O, and still more preferably an oxygen atom.

According to a preferred embodiment of the present invention, in the compound of formula (I), R ₁ is a hydrogen atom, or COR ₄ (where R ₄ is a C _1-4 alkyl group, OR ₅ (where R ₅ represents a C _1-4 alkyl group), or NR ₆ R ₇ (wherein R ₆ and R ₇ independently of each other represent a hydrogen atom or a C _1-18 alkyl group). ).

Also according to a preferred embodiment of the present invention, in the compound of formula (I), R ₂ represents a C _1-4 alkyl group.

According to a preferred embodiment of the present invention, in the compound of formula (I), R ₃ represents a C _1-4 alkyl group.

According to another preferred embodiment of the present invention, in the compound of formula (I), R ₂ and R ₃ together represent — (CH ₂ ) _m — (m is 3 or 4). .

Also according to a preferred embodiment of the present invention, in the compound of formula (I), X ₁ and X ₂ are independently of each other a hydrogen atom, a halogen atom or a C ₁ -optionally substituted C _{1- 4 represents} an alkyl group, a C _1-4 alkyloxy group, or a C _1-4 alkyloxycarbonyl group. However, X ₁ and X ₂ do not represent a hydrogen atom at the same time.

According to a preferred embodiment of the present invention, in the compound of formula (I), X ₃ represents a hydrogen atom.

Further, according to a preferred embodiment of the present invention, in the compounds of formula _{(I), W 1, W} 2, and _{W 3} represent _{C-Y 1, C-Y} 2, and _{C-Y 3,} respectively.

Also according to a preferred embodiment of the present invention, in the compound of formula (I), Y ₁ , Y ₂ , Y ₃ , Y ₄ and Y ₅ are independently of each other a hydrogen atom, C _1-8 alkyl A group (the C _1-8 alkyl group is substituted by one or more halogen atoms which are the same or different), a C _1-8 alkyloxy group (the C _1-8 alkyloxy group is the same or different The above halogen atom and / or a C _1-4 alkyloxy group substituted by one or more same or different halogen atoms), a C _1-8 alkylthio group (this C _1-8 alkylthio group) Are substituted with one or more halogen atoms which are the same or different), or represent a halogen atom. Provided that at least one of Y ₁ , Y ₂ , Y ₃ , Y ₄ , and Y ₅ is a C _1-8 alkyl group (this C _1-8 alkyl group is substituted by one or more halogen atoms, which are the same or different). A C _1-8 alkyloxy group (wherein this C _1-8 alkyloxy group is one or more halogen atoms which are the same or different, and / or C ₁ substituted by one or more halogen atoms which are the same or different) _-4 alkyloxy group), or a C _1-8 alkylthio group (this C _1-8 alkylthio group is substituted by one or more halogen atoms which are the same or different).

According to another preferred embodiment of the present invention, in the compound of formula (I), Y ₁ , Y ₂ , Y ₃ , Y ₄ , and Y ₅ are a combination of two adjacent groups, It represents —O— (CH ₂ ) _n —O— (where n represents 1 or 2) substituted with one or more halogen atoms.

According to a preferred embodiment of the present invention, in the compound of formula (I), Z represents an oxygen atom, OCH ₂ , or O (CH ₂ ) ₃ O.

According to a preferred embodiment of the present invention, the compound of formula (I) is
R ₁ is a hydrogen atom, or COR ₄ (where R ₄ is a C _1-4 alkyl group, OR ₅ (where R ₅ is a C _1-4 alkyl group)), or NR ₆ R ₇ (wherein R ₆ and R ₇ independently of each other represent a hydrogen atom or a C _1-18 alkyl group),
R ₂ represents a C _1-4 alkyl group,
R ₃ represents a C _1-4 alkyl group,
Alternatively, R ₂ and R ₃ together represent — (CH ₂ ) _m — (where m is 3 or 4);
X ₁ and _{X 2} are, independently of one another, a hydrogen atom, a halogen atom, an alkyl group optionally _{C 1-4} optionally substituted by a halogen _atom, an alkyl group of _{C 1-4} or _{C 1-4,} Represents an alkyloxycarbonyl group,
However, X ₁ and X ₂ do not represent a hydrogen atom at the same time,
X ₃ represents a hydrogen atom,
W _{1, W 2,} and _{W 3} are, represent _{C-Y 1, C-Y} 2, and _{C-Y 3,} respectively,
Y ₁ , Y ₂ , Y ₃ , Y ₄ , and Y ₅ are each independently a hydrogen atom, a C _1-8 alkyl group (wherein the C _1-8 alkyl group is the same or different from one or more halogen atoms) A C _1-8 alkyloxy group (this C _1-8 alkyloxy group is substituted by one or more halogen atoms which are the same or different and / or one or more halogen atoms which are the same or different) A C _1-4 alkyloxy group), a C _1-8 alkylthio group (this C _1-8 alkylthio group is substituted by one or more halogen atoms which are the same or different), or Represents a halogen atom,
Provided that at least one of Y ₁ , Y ₂ , Y ₃ , Y ₄ , and Y ₅ is a C _1-8 alkyl group (this C _1-8 alkyl group is substituted by one or more halogen atoms, which are the same or different). A C _1-8 alkyloxy group (wherein this C _1-8 alkyloxy group is one or more halogen atoms which are the same or different, and / or C ₁ substituted by one or more halogen atoms which are the same or different) _-4 alkyloxy group), or a C _1-8 alkylthio group (this C _1-8 alkylthio group is substituted by one or more halogen atoms which are the same or different),
_{Alternatively, Y 1, Y 2, Y} 3, Y 4, and _{Y 5} is two adjacent groups are taken together, -O- substituted by one or more halogen atoms _{(CH 2)} n -O -(Where n represents 1 or 2),
Z represents an oxygen atom, OCH ₂ , or O (CH ₂ ) ₃ O. The compound of formula (I) according to this embodiment is recognized as having a particularly excellent insecticidal effect in WO 2006/13896.

According to a particularly preferred embodiment of the invention, the compound of formula (I) is
R ₁ represents COR ₄ or COOR ₅ (where R ₄ and R ₅ represent a C _1-4 alkyl group),
R ₂ represents a C _1-4 alkyl group,
R ₃ represents a C _1-4 alkyl group,
X ₁ and X ₂ each independently represent a hydrogen atom or a C _1-4 alkyl group which may be substituted with a halogen atom;
However, X ₁ and X ₂ do not represent a hydrogen atom at the same time,
X ₃ represents a hydrogen atom,
W _{1, W 2,} and _{W 3} are, represent _{C-Y 1, C-Y} 2, and _{C-Y 3,} respectively,
Y ₁ , Y ₂ , Y ₃ , Y ₄ , and Y ₅ are each independently a hydrogen atom, a C _1-8 alkyloxy group (wherein the C _1-8 alkyloxy group is the same or different one or more halogen atoms) An atom, and / or a C _1-4 alkyloxy group substituted by one or more same or different halogen atoms), or a halogen atom,
Provided that at least one of Y ₁ , Y ₂ , Y ₃ , Y ₄ , and Y ₅ is a C _1-8 alkyloxy group (the C _1-8 alkyloxy group is the same or different one or more halogen atoms, And / or is substituted by a C _1-4 alkyloxy group substituted by one or more same or different halogen atoms, or Y ₁ , Y ₂ , Y ₃ , Y ₄ , and Y ₅ May represent —O— (CH ₂ ) _n —O— (where n represents 1 or 2), in which two adjacent groups are combined and substituted by one or more halogen atoms. ,
Z represents an oxygen atom.

According to a further particularly preferred embodiment of the invention, the compound of formula (I) is
R ₁ represents COR ₄ or COOR ₅ (where R ₄ and R ₅ represent a C _1-4 alkyl group),
R ₂ represents a methyl group,
R ₃ represents an ethyl group,
X ₂ represents a methyl group, X ₁ and X ₃ represent a hydrogen atom,
W _{1, W 2,} and _{W 3} are, represent _{C-Y 1, C-Y} 2, and _{C-Y 3,} respectively,
Y ₃ represents a trifluoromethoxy group or a tetrafluoroethoxy group, Y ₁ , Y ₂ , Y ₄ , and Y ₅ represent a hydrogen atom,
Alternatively, Y ₂ and Y ₃ may be combined to represent —O— (CF ₂ ) ₂ —O— (, where Z represents an oxygen atom.

  Examples of the agriculturally and horticulturally acceptable salt of the compound of the formula (I) include acid addition salts such as hydrochloride, nitrate, sulfate, phosphate, and acetate.

  Specific examples of the compound of formula (I) or an agricultural and horticulturally acceptable salt thereof that are preferable as the active ingredient of the composition according to the present invention include compounds shown in Tables 1 to 28 below. The compounds shown in Tables 1 to 28 can be produced by the methods described in International Publication No. 2006/13896 pamphlet and Japanese Patent Application Laid-Open No. 2008/110953.

Other Pest Control Agent In the present invention, the other pest control agent used together with the compound of formula (I) may be any control agent for protecting useful plants from pests in agriculture or horticulture, Examples include insecticides, fungicides, acaricides, herbicides, and plant growth regulators. Specific drugs include, for example, the Pesticide Manual (The Pesticide Manual, 14th edition, 2006, published by The British Crop Protection Council) and Shibuya Index (SHIBUYA INDEX 13th edition, 2008, published by SHIBUYA INDEX RESEARCH GROUP). Those described are mentioned. Other pest control agents are preferably insecticides and / or fungicides, more preferably insecticides.

  Preferred examples of insecticides used with the compounds of formula (I) include acephate, dichlorvos, EPN, fenitrothion, fenamifos, prothiofos, profenfos, profenofos, pyracrofos. (Pyraclofos), chlorpyrifos-methyl, chlorfenvinphos, demeton, ethion, malathion, coumaphos, isoxathion, fenthion, Organophosphorus insecticides such as diazinon; thiodicarb, aldicarb, oxamyl, propoxur, carbaryl, fenobucarb, ethiofencarb, fenothiocarb ( fenothiocarb), Such as fenoxycarb, pirimicarb, carbofuran, carbosulfan, furathiocarb, hyquincarb, alanycarb, methomyl, benfuracarb Carbamate insecticides; nereistoxin insecticides such as cartap, thiocyclam, and bensultap; organochlorine insecticides such as dicofol and tetradifon; acrinathrin ), Bifenthrin, cycloprothrin, cyfluthrin, dimefluthrin, empenthrin, fenfluthrin, fenpropathrin, imiprothrin, fluprothrin, metofluthrin), permethr in), phenothrin, resmethrin, teflutrin, tetramethrin, tralomethrin, transfluthrin, cypermethrin, deltamethrin, cyhalothrin , Pyrethroid insecticides such as fenvalerate, fluvalinate, etofenprox, flufenprox, halfenprox, silafluofen, dimefluthrin Diflubenzuron, teflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, penfluron, trifluromuron; (triflumuron), chlorfluazuron, diafenthiuron, urea insecticides such as hydramethylnon; halofenozide, tebufenozide, methoxyfenozide, chromafenozide Benzoylphenylurea insecticides such as (chromafenozide); imidacloprid, nitenpyram, clothianidin, acetamiprid, acetamiprid, dinotefuran, thiacloprid, iamethoxam thiamethoxam Neonicotinoid insecticides; phenylpyrazole insecticides such as ethiprole, fipronil, pyrafluprole, pyriprole; and pyridaben, fenpyroximate (Fenpyroxymate), flufenerim, pyrimidifen, tebufenpyrad, tolfenpyrad, fluacrypyrim, acequinocyl, cyflumetofrene, rompymedin Proxyfen (pyriproxyfen), etoxazole, dicyclanil, buprofezin, hexythiazox, amitraz, chlordimeform, pymetrozine, bifenazate, bifenazate (bifenazate) spirodiclofen, spiromesifen, spirotetramat, flonicamid, chlorfenapyr, indoxacarb, indoxacarb Ril (pyridalyl), avermectin (avermectin), milbemectin (milbemectin), lepimectin (lepimectin), quinomethionate, azadirachtin, nicotine, rotenone, BT agent, insect pathogenic virus agent, emamectin benzoate Acid salt (emamectin benzoate), spinosad (spinosad), spinetoram (pyrinefluquinazon), flubendiamide (flubendiamide), chlorantraniliprole (chlorantraniliprole), ciazapyr (cyenopyrafen) (cyenopyrafen) ), Fenazaflor, triazamate, and sulfoxaflor.

  According to a preferred embodiment of the invention, the insecticide used with the compound of formula (I) is diazinon, methomyl, cartap, cypermethrin, flufenoxuron, Acequinocyl, imidacloprid, chlorfenapyr, spinosad, pymetrozine, tolfenpyrad, emamectin benzoate, methenprox, ethenprox, ethenprox ), Flubendiamide, bifenazate, ethiprole, indoxacarb, pyridalyl, milbemectin, quinomethionate, acrinathrin, acephate It is assumed to be selected from the group consisting of thiocyclam (thiocyclam), particularly preferably pyridalyl (pyridalyl).

  Examples of fungicides used with the compound of formula (I) include azoxystrobin, kresoxym-methyl, trifloxystrobin, oryzastrobin, picoxystrobin Strobilin compounds such as picoxystrobin and fuoxastrobin; anilinopyrimidine compounds such as mepanipyrim and pyrimethanil and cyprodinil; triadimefon and bitertanol , Triflumizole, etaconazole, propiconazole, penconazole, flusilazole, microbutanil, cyproconazole, tebuconazole, hexaconazole (hexaconazole), professional Azole compounds such as prochloraz, simeconazole; quinoxaline compounds such as quinomethionate; maneb, zineb, mancozeb, polycarbamate, provineb ( dithiocarbamate compounds such as propineb; phenylcarbamate compounds such as diethofencarb; organochlorine compounds such as chlorothalonil and quintozene; benomyl and thiophanate-methyl Benzimidazole compounds such as carbendazole; phenylamide compounds such as metalaxyl, oxadixyl, ofurase, benalaxyl, furalaxyl, cyprofuram; Dichlorfluani Sulfenic acid compounds such as dichlofluanid; copper compounds such as cupric hydroxide and oxine-copper; isoxazole compounds such as hydroxyisoxazole Organic phosphorus compounds such as fosetyl-aluminium and tolclofos-methyl; N-halogenothioalkyl compounds such as captan, captafol and folpet Dicarboxyimide compounds such as procymidone, iprodione and vinchlozolin; benzanilide compounds such as flutolanil and mepronil; fenpropimorph and dimethomorph ) Morpholine compounds such as triphenyltin hydroxide, vinegar Organotin compounds such as fenthin acetate; Cyanopyrrole compounds such as fludioxonil and fenpiclonil; and fthalide, probenazole, acibenzolar-S -methyl), thiadinil, isothianil, carpropamid, diclocymet, fenoxanil, tricyclazole, pyroquilon, ferimzone, fluazinam, fluazinam (cymoxanil), triforine, pyrifenox, fenarimol, fenpropidin, pencicuron, cyazofamid, cyflufenamid, boscalid, pentiopyrad penthiopyrad), professional Nazido, quinoxyfen, famoxadone, fenamidone, iprovalicarb, benchthiavalicarb-isopropyl, fluopicolide, pyribencarbs, ugagamycin Validamycin, amisulbrom, ethaboxam, mandipropamid and tebufloquin.

According to another aspect of the invention, preferred combinations include:
A compound of formula (I) in which R ₁ represents COR ₄ or COOR ₅ (where R ₄ and R ₅ represent a C _1-4 alkyl group);
R ₂ represents a C _1-4 alkyl group,
R ₃ represents a C _1-4 alkyl group,
X ₁ and X ₂ each independently represent a hydrogen atom or a C _1-4 alkyl group which may be substituted with a halogen atom;
However, X ₁ and X ₂ do not represent a hydrogen atom at the same time,
X ₃ represents a hydrogen atom,
W _{1, W 2,} and _{W 3} are, represent _{C-Y 1, C-Y} 2, and _{C-Y 3,} respectively,
Y ₁ , Y ₂ , Y ₃ , Y ₄ , and Y ₅ are each independently a hydrogen atom, a C _1-8 alkyloxy group (wherein the C _1-8 alkyloxy group is the same or different one or more halogen atoms) An atom, and / or a C _1-4 alkyloxy group substituted by one or more same or different halogen atoms), or a halogen atom,
Provided that at least one of Y ₁ , Y ₂ , Y ₃ , Y ₄ , and Y ₅ is a C _1-8 alkyloxy group (the C _1-8 alkyloxy group is the same or different one or more halogen atoms, And / or is substituted by a C _1-4 alkyloxy group substituted by one or more same or different halogen atoms)
_{Alternatively, Y 1, Y 2, Y} 3, Y 4, and _{Y 5} is two adjacent groups are taken together, -O- substituted by one or more halogen atoms _{(CH 2)} n -O -(Where n represents 1 or 2), Z represents an oxygen atom, and combinations of insecticides include diazinon, metomyl, cartap, cypermethrin. (cypermethrin), flufenoxuron, acequinocyl, imidacloprid, chlorfenapyr, spinosad, pymetrozine, tolfenpyrad, and benzoate , Etofenprox, permethrin, flubendiamide, bifenazate selected from the group consisting of te), ethiprole, indoxacarb, pyridalyl, milbemectin, quinomethionate, acrinathrin, acephate, thiocyclam Particularly preferred is pyridalyl.

According to another aspect of the invention, particularly preferred combinations include:
A compound of formula (I) in which R ₁ represents COR ₄ or COOR ₅ (where R ₄ and R ₅ represent a C _1-4 alkyl group);
R ₂ represents a methyl group,
R ₃ represents an ethyl group,
X ₂ represents a methyl group, X ₁ and X ₃ represent a hydrogen atom,
W _{1, W 2,} and _{W 3} are, represent _{C-Y 1, C-Y} 2, and _{C-Y 3,} respectively,
Y ₃ represents a trifluoromethoxy group or a tetrafluoroethoxy group, Y ₁ , Y ₂ , Y ₄ , and Y ₅ represent a hydrogen atom,
Alternatively, Y ₂ and Y ₃ may be taken together to represent —O— (CF ₂ ) ₂ —O—, wherein Z represents an oxygen atom, and as a combination insecticide, diazinon, Methomyl, cartap, cypermethrin, flufenoxuron, acequinocyl, imidacloprid, chlorfenapyr, spinosad, pimetroine, pymetroine (pymetroine) tolfenpyrad) and emamectin benzoate, etofenprox, permethrin, flubendiamide, bifenazate, ethiprole, indoxacarb, pyridalyl pyridalyl), milbemectin, quinomethionate (qui It is selected from the group consisting of nomethionate, acrinathrin, acephate, thiocyclam, and particularly preferably pyridalyl.

Pest control composition and pest control method The pest control composition according to the present invention comprises at least one compound of the above-mentioned formula (I) or an agricultural and horticulturally acceptable salt thereof, and other harmful compounds described above. It comprises at least one biocontrol agent as an active ingredient.

  According to a preferred embodiment of the present invention, the pest control composition further comprises an agriculturally and horticulturally acceptable carrier. Such a carrier is appropriately selected by those skilled in the art depending on the form (dosage form) of the composition. Compositions include emulsions, solutions, emulsions, wettable powders, granular wettable powders, flowable powders, powders, DL powders, granules, fine granules F, tablets, oils, aerosols, smokes, micros Various dosage forms such as capsules can be mentioned. These various dosage forms can be found in, for example, the “Agricultural Chemicals Formulation Guide” (edited by the Japanese Pesticide Science Society / Application Law Study Group, published by the Japan Plant Protection Association, 1997) Can be produced by the methods described.

  Usable carriers include solid carriers, liquid carriers, gaseous carriers, surfactants, dispersants and other formulation aids.

  Examples of the solid carrier include talc, bennite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, calcium carbonate, and the like.

  Examples of the liquid carrier include alcohols such as methanol, n-hexanol and ethylene glycol, ketones such as acetone, methyl ethyl ketone and cyclohexanone, aliphatic hydrocarbons such as n-hexane, kerosene and kerosene, toluene, xylene and methyl Aromatic hydrocarbons such as naphthalene, ethers such as diethyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, nitriles such as acetonitrile and isobutyronitrile, acid amides such as dimethylformamide and dimethylacetamide, soybean Examples include oils, vegetable oils such as cotton seed drops, dimethyl sulfoxide, and water.

  Examples of the gaseous carrier include LPG, air, nitrogen, carbon dioxide gas, dimethyl ether and the like.

  Surfactants and dispersants for emulsification, dispersion, spreading, etc. include, for example, alkyl sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters, Examples include lignin sulfonate.

  Moreover, as an adjuvant for improving the property of a formulation, carboxymethylcellulose, gum arabic, polyethylene glycol, calcium stearate etc. are mentioned, for example.

  The above carriers, surfactants, dispersants, and adjuvants may be used alone or in combination as necessary.

  The amount of the active ingredient in the composition for controlling pests according to the present invention is 0.1 to 99.9% by weight, preferably 0.2 to 80% by weight in the total amount. Moreover, the mixing ratio of the compound of the formula (I) and other pest control agents can be varied over a wide range. The pest control composition according to the invention generally contains 0.1 to 80% by weight of the compound of formula (I) and 0.1 to 80% by weight of other pest control agents.

According to a preferred embodiment of the present invention, a pest control composition according to the present invention comprises a wettable powder, a granular wettable powder, a flowable powder, an emulsion, a powder, a DL powder, a fine powder F, a granular, a microcapsule. Or in the form of an emulsion. Preferred pest control compositions of these forms include the following compositions:
(1) 0.1 to 80% by weight of a compound represented by the formula (I) or an agricultural and horticulturally acceptable salt thereof, 0.1 to 80% by weight of an insecticide as another pest control agent, 0 A wettable powder composition containing 6-30 wt% wetting and dispersing agents and 10-99 wt% bulking agent;
(2) 0.1 to 80% by weight of the compound represented by the formula (I) or an agricultural and horticulturally acceptable salt thereof, 0.1 to 80% by weight of an insecticide as another pest control agent, 0 A composition in the form of a water dispersible granule containing 6-30% by weight of a wetting agent, a dispersant and a binder, and 10-99% by weight of a bulking agent;
(3) 0.1 to 80% by weight of the compound represented by the formula (I) or an agricultural and horticulturally acceptable salt thereof, 0.1 to 80% by weight of an insecticide as another pest control agent, 1 A flowable composition comprising -40% by weight dispersant, thickener, antifreeze, preservative and antifoam agent, and 10-99% by weight water;
(4) 0.1 to 80% by weight of a compound represented by the formula (I) or an agricultural and horticulturally acceptable salt thereof, 0.1 to 80% by weight of an insecticide as another pest control agent, 1 An emulsifiable concentrate composition containing -30 wt% emulsifier and emulsion stabilizer, and 10-99 wt% organic solvent;
(5) 0.1 to 80% by weight of a compound represented by the formula (I) or an agricultural and horticulturally acceptable salt thereof, 0.1 to 80% by weight of an insecticide as another pest control agent, and A dust composition comprising 19 to 99.8% by weight of a bulking agent;
(6) 0.1 to 80% by weight of the compound represented by formula (I) or an agricultural and horticulturally acceptable salt thereof, 0.1 to 80% by weight of an insecticide as another pest control agent, and A composition in DL powder form, containing 19-99.8% by weight of bulking agent;
(7) 0.1 to 80% by weight of a compound represented by the formula (I) or an agricultural and horticulturally acceptable salt thereof, 0.1 to 80% by weight of an insecticide as another pesticide, 0 A composition in microgranule fine form, containing from 2 to 10% by weight of solvent or binder, and from 19 to 99.6% by weight of bulking agent;
(8) 0.1 to 80% by weight of the compound represented by the formula (I) or an agricultural and horticulturally acceptable salt thereof, 0.1 to 80% by weight of an insecticide as another pesticide, 0 Granule composition containing 5-30% by weight granulation aid (surfactant) and binder, and 18-99.6% by weight extender;
(9) 0.1 to 80% by weight of a compound represented by the formula (I) or an agricultural and horticulturally acceptable salt thereof, 0.1 to 80% by weight of an insecticide as another pest control agent, A composition in microcapsule form containing -50% by weight coating agents, emulsifiers, dispersants and preservatives, and 20-98.8% by weight water; and
(10) 0.1 to 80% by weight of a compound represented by the formula (I) or an agricultural and horticulturally acceptable salt thereof, 0.1 to 80% by weight of an insecticide as another pest control agent, ~ 50 wt% organic solvent, 2-20 wt% emulsifier, 0.01-20 wt% thickener, antifreeze, preservative and antifoam agent, and 10-96.7 wt% water. A composition in emulsion form (emulsion) is included.

  According to another aspect of the present invention, the pest control composition according to the present invention is applied to the target pest, the target useful plant, the seed of the target useful plant, the soil, or the cultivation carrier. A method of protecting useful plants from is provided. The composition for controlling pests according to the present invention may be applied as it is, or may be applied after dilution.

  According to another aspect of the present invention, there is provided the use of the pest control composition according to the present invention for protecting useful plants from pests.

  Specific means for applying the composition for controlling pests according to the present invention to target pests, target useful plants, seeds of target useful plants, soil or cultivation carriers include spraying treatment, soil treatment, surface treatment or fumigation treatment, etc. Is mentioned. Examples of the spraying treatment include spraying, spraying, misting, atomizing, dusting, and water surface application. Examples of soil treatment include soil irrigation and soil mixing. Examples of the surface treatment include application, powder coating, and coating. Moreover, as a fumigation process, covering soil with a poly film after soil injection | pouring is mentioned, for example. Thus, the method according to the invention also includes a method of applying by fumigation in a sealed space.

  The composition for controlling pests according to the present invention can be prepared in advance as described above. However, the compound represented by the above formula (I), which is an active ingredient in the composition, or the agriculture and horticulture thereof. A preparation comprising each of the above-acceptable salts and the above-mentioned other pesticides alone may be prepared, and when used, they may be mixed and used on the spot.

  Therefore, according to another aspect of the present invention, at least one compound represented by the above formula (I) or an agriculturally and horticulturally acceptable salt thereof and at least one other pesticide as described above are used. A combination with is provided.

  According to a preferred embodiment of the present invention, in the combination, the compound represented by formula (I) or an agriculturally and horticulturally acceptable salt thereof is provided as a first composition comprising it as an active ingredient. And other pesticidal agents are provided as a second composition comprising it as an active ingredient. Here, the 1st composition and the 2nd composition can be made into arbitrary dosage forms combining an appropriate carrier or adjuvant similarly to the above-mentioned composition for controlling pests. This combination may be provided in the form of a drug set.

  According to another aspect of the present invention, there is provided a method for protecting useful plants from pests, comprising at least one compound represented by the above formula (I) or an agriculturally and horticulturally acceptable salt thereof, and There is provided a method comprising applying at least one of the other pest control agents simultaneously or separately to the target pest, the target useful plant, the seed of the target useful plant, the soil, or the cultivation carrier. .

  In this method, to apply “simultaneously”, at least one compound represented by formula (I) or an agriculturally and horticulturally acceptable salt thereof, and at least one other pesticide, It also includes mixing before application and applying the mixture. To apply “separately”, the compound represented by formula (I) or an agricultural and horticulturally acceptable salt thereof is applied prior to other pest control agents without premixing them. And the application of the compound represented by the formula (I) or an agricultural and horticulturally acceptable salt thereof after other pest control agents.

According to a preferred embodiment of the present invention, a method for protecting useful plants from pests, comprising:
(A) a first composition comprising, as an active ingredient, at least one compound represented by the above formula (I) or an agricultural and horticulturally acceptable salt thereof;
(B) the target pest, the target useful plant, the seed of the target useful plant, the soil, simultaneously or separately with the second composition comprising at least one of the other pest control agents described above as an active ingredient Or a method comprising applying to a cultivation carrier is provided.

Examples of the insect species to be controlled in the present invention, that is, the insect species for which the composition and combination according to the present invention exhibit a controlling effect include the following insect species: Thripidae, Phlaeothripidae, Aeolothripidae, etc .; Lepidoptera , Moths such as worms, Helicobelpa pests, Heliotis pests (Noctuidae); Japanese moths (Pyralidae, Crambidae) such as green corn borer, European corn borer; Pieridae such as white butterfly ); Chasohosoga, etc. (Gracillariidae); Adoxofies, Nashihimeshinsui, Codlinga, etc. Tortricidae; Momoshiniga, etc. Carposinidae; Skeletons (Lymantriidae); Sugas such as Japanese pear (Yponomeutidae); Swamps such as cotton beetle (Gelechiidae); Hitriggers (Arctiidae) such as white-headed beetle; Hemiptera (such as Sesiidae); Hemiptera pests (for example, whitefly such as tobacco whitefly, whitefly whitefly) (Aleyrodidae); aphids such as peach aphid, cotton aphid Leafhoppers (Cicadellidae) such as Nomitorihimebae and Phatenophyllum (Cicadellidae); Leafhoppers such as brown planthopper, leafhopper, and white-spotted plant (Delphacidae, Cixiidae, Meenoplidae, Derbidae, Issidae, Lophopidae); Bugs such as turtles (Miridae, Tingidae, Acanthosomatidae, Cydnidae, Dinidoridae, Pentatomidae, Plataspidae, Scutelleridae, Urostylidae, Berytidae, Lygaeidae, Malcidae, Largidae, Pyrrhocoridae, Alyd Scale insects (Diaspididae, Margarodidae, Ortheziidae, Aclerdiae, Dactylopiidae, Kerridae, Pseudococcidae, Coccidae, Eriococcidae, Asterolecaniidae, Beesidaidae, Lecanodiaspididae, Cercocidae, Calcoididae; ae), etc.); Coleoptera such as Coleoptera (Bruchidae, Anthribidae, Brentidae, Apionidae, Curculionidae, Erirhinidae, Dryophthoridae); Beetles (Scarabaeidae) such as rice beetle; Chrysomelidae such as rice beetle, kissing beetle, cucumber potato beetle, Colorado potato worm, Western corn rootworm, Southern corn rootworm; (Scolytidae, Platypodidae, Lyctidae); Epilacunas (Coccinellidae) such as Alaska weevil; Cerambycidae, etc .; Spider mites (Tetranychidae, Tenuipalpidae) such as citrus spider mites, apple spider mites, Oligonicus; Dust mites (Tarsonemidae) such as mite dust mites; House dust mites (Epidermoptidae); house dust mites (Psoroptidae); house dust mites (Sarcoptidae); claw mites; Dermanyssidae; , Bees (Tenthredinidae, Pamphiliidae, Argidae, Cimbicidae, Diprionidae); hornets (Wespidae); , Grasshoppers, keratoids, etc. (Tettigoniidae, Gryllidae, Oecanthidae, Mogoplistidae, Gryllotalpidae, Pyrgomorphidae, Acrididae, Tetrigidae)); (Cecidomyiidae); fruit flies (Tephritidae); house flies (Muscidae, Fanniidae); moths (Tipulidae); (Sarcophagidae); such as Anthomyiidae); plant parasitic nematodes (eg, Tylenchulidae such as southern nematode nematodes; cyst nematodes such as potato cyst nematodes (Heteroderidae); Root-knot nematodes (M eloidogynidae); Aphelenchoididae; Telotylenchidae; Coleonematidae; Pinatium (Paratylenchidae); Longidoridae; Trichodolidae; For example, German cockroaches, American cockroaches, Black cockroaches, Great cockroaches, Great cockroaches (Blattidae, Blattellidae); Termite eyes (Kalotermitidae, Rhinotermitidae, Termitidae); , Haematopinidae, Hoplopleuridae, Linognathidae, Pediculidae, Polyplacidae, Pthiridae, Menoponidae, Trichodectidae); Ticks, pests Or is a Hemiptera, is more preferably Thysanoptera pests and lepidopteran pests or Hemiptera.

  EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated concretely, this invention is not limited to these Examples. Compound 120 and compound 190 used in the examples were synthesized by the method described in WO2006 / 13896.

[Formulation example]
Formulation Example 1 [wettable powder]
Compound 120 2% by weight
Diazinon 40% by weight
37% by weight of clay
2% white carbon
Diatomaceous earth 14% by weight
Calcium lignin sulfonate 4% by weight
Sodium lauryl sulfate 1% by weight

  The above ingredients were mixed uniformly and pulverized to obtain a wettable powder.

Formulation Example 2 [Granular wettable powder]
Compound 120 2% by weight
Torfenpyrad 20% by weight
68% by weight of clay
Dextrin 5% by weight
Alkyl maleic acid copolymer 4% by weight
Sodium lauryl sulfate 1% by weight

  The above components were uniformly pulverized and mixed, water was added and kneaded well, and then granulated and dried to obtain a granular wettable powder.

Formulation Example 3 [Flowable Agent]
Compound 120 2% by weight
Acequinosyl 30% by weight
POE polystyryl phenyl ether sulfate 5% by weight
Propylene glycol 6% by weight
Bentonite 1% by weight
Xanthan gum 1% aqueous solution 3% by weight
PRONAL EX-300 (Toho Chemical Co., Ltd.) 0.05% by weight
ADDAC 827 (Kay Kasei Co., Ltd.) 0.02% by weight
100% by weight of water

  The total amount excluding the 1% aqueous solution of xanthan gum and an appropriate amount of water from the above blend was premixed and then pulverized with a wet pulverizer. Thereafter, a flowable agent was obtained by adding a 1% aqueous solution of xanthan gum and the remaining water to a total of 100% by weight.

Formulation Example 4 [Emulsion]
Compound 120 2% by weight
Cypermethrin 10% by weight
N, N-dimethylformamide 20% by weight
Solvesso 150 (ExxonMobil Co., Ltd.) 58% by weight
10% by weight of polyoxyethylene alkyl aryl ether

  The above ingredients were uniformly mixed and dissolved to obtain an emulsion.

Formulation Example 5 [powder]
Compound 190 0.5% by weight
Torfenpyrad 1.5% by weight
60% clay
Talc 37% by weight
Calcium stearate 1% by weight

  The said component was mixed uniformly and the powder agent was obtained.

Formulation Example 6 [DL powder]
Compound 190 1% by weight
Imidacloprid 1% by weight
DL clay 94.5% by weight
2% white carbon
Calcium stearate 1% by weight
Light liquid paraffin 0.5% by weight

  The said component was mixed uniformly and the powder agent was obtained.

Formulation Example 7 [Fine Granule F]
Compound 190 1% by weight
Acequinosyl 1% by weight
Carrier 94% by weight
2% white carbon
Hyzol SAS-296 2% by weight

  The above ingredients were mixed uniformly to obtain a powder.

Formulation Example 8 [Granule]
Compound 120 5% by weight
Imidacloprid 2% by weight
Bentonite 40% by weight
Talc 10% by weight
41% by weight clay
2% by weight calcium lignin sulfonate

  The above components were pulverized and mixed uniformly, kneaded well with water, and granulated and dried to obtain granules.

Formulation Example 9 [Microcapsule]
Compound 120 2% by weight
Imidacloprid 3% by weight
25% by weight of urethane resin
Emulsifying / dispersing agent 5% by weight
Preservative 0.2% by weight
64.8% by weight of water

  A microcapsule was obtained by forming a urethane resin film on the surfaces of the compound 120 particles and imidacloprid particles using the above-described components by interfacial polymerization.

Formulation Example 10 [Emulsion]
Compound 120 2% by weight
Diazinon 5% by weight
Hyzol SAS-296 20% by weight
1% by weight of PVA 5% aqueous solution
Emulsifying / dispersing agent 10% by weight
5% by weight of propylene glycol
PRONAL EX-300 (Toho Chemical Co., Ltd.) 0.05% by weight
ADDAC 827 (Kay Kasei Co., Ltd.) 0.02% by weight
Water 56.93 wt%

  An oil phase in which an insecticidal component and an emulsifying / dispersing agent were dissolved in Hysol SAS-296 was prepared. Other components were separately mixed and dissolved to prepare an aqueous phase. The emulsion was emulsified with a homomixer while gradually adding the aqueous phase to the oil phase to obtain an emulsion.

[Test example]
Test Example 1: Golden moth control test pot A leaf disk having a diameter of 5 cm was cut out from cabbage grown in a pot and placed in a 200 cc plastic cup. To this, the composition of the present invention prepared so that the compound 120 shown in Table 5 and other insecticides had the predetermined concentrations shown in Table 29 and Table 30 was added 50% acetone water (0.33% new gramine added). 1) or a chemical solution diluted with 50% aqueous acetone (added with 0.33% new gramine) so as to have a predetermined concentration of each drug was sprayed. After air-drying, 5 koganaga second instar larvae were released. Then, the plastic cup was covered and left still in a constant temperature room at 25 ° C. (16 hours light period-8 hours dark period). The insects were observed for life and death 3 days after the release, and the death rate was calculated according to the following formula. The results were as shown in Tables 29 and 30.
Death rate (%) = {Number of deaths / (Number of living insects + Number of dead insects)} × 100

Moreover, the theoretical value when there is no synergistic effect was calculated by the following Colby equation. The results were as shown in Table 31 and Table 32.
Colby's formula: Theoretical value (%) = 100− (A × B) / 100
(A: 100- (Dead rate when only Compound A is applied); B: 100- (Death rate when only Compound B is applied))

  The observed values of mortality shown in Tables 29 and 30 are clearly higher than the theoretical values shown in Tables 31 and 32, and thus the compounds of formula (I) and the drugs shown in Tables 29 and 30 It was proved that the combination with shows a synergistic effect.

Test Example 2: Citrus thrips control test A leaf disk having a diameter of 2.8 cm was cut out from the green beans grown in a pot, and placed on a moist absorbent cotton in a 5.0 cm petri dish. To this, the composition of the present invention prepared so that the compound 120 shown in Table 5 and other insecticides had the predetermined concentrations shown in Tables 33, 34 and 35 was added 50% acetone water (0.33% new gramine). The test solution diluted with (addition)) or the chemical solution diluted with 50% acetone water (addition of 0.33% new gramine) so as to obtain a predetermined concentration of each drug alone was sprayed. After air-drying, 10 first-instar larvae of Citrus thrips were released. Then, the petri dish was covered and left still in a thermostatic chamber (16 hours light period-8 hours dark period) at 25 ° C. The insects were observed for life and death 3 days after the release, and the death rate was calculated according to the following formula. The results were as shown in Tables 33, 34 and 35.
Death rate (%) = {Number of dead insects / (Number of living insects tens of dead insects)} × 100
When death was observed in the untreated area, the corrected death rate was calculated according to the ABBOTT correction formula shown below. The results were as shown in Tables 33, 34, and 35.
Corrected death rate (%) = {(survival rate of untreated group−survival rate of treated group) / survival rate of untreated group} × 100

Moreover, the theoretical value when there is no synergistic effect was calculated by the following Colby equation. The results were as shown in Tables 36, 37, and 38.
Colby's formula: Theoretical value (%) = 100− (A × B) / 100
(A: 100- (Dead rate when only Compound A is applied); B: 100- (Death rate when only Compound B is applied))

  The observed mortality rates shown in Tables 33, 34, and 35 are clearly higher than the theoretical values shown in Tables 36, 37, and 38, so that the compounds of formula (I) and Table 33, It was demonstrated that combinations with the drugs shown in 34 and 35 show a synergistic effect.

Test Example 3: Tobacco whitefly adult test test A leaf disc having a diameter of 8 cm was cut out from a cucumber cultivated in a pot and placed on a damp cotton wool with the back of the leaf facing up. To this, the composition of the present invention prepared so that the compound 120 shown in Table 5 and other insecticides had the predetermined concentrations shown in Table 39 was added with 50% aqueous acetone (added with 0.33% new gramine). A diluted test solution or a chemical solution diluted with 50% acetone water (adding 0.33% new gramine) so as to have a predetermined concentration of each drug was sprayed. After air drying, this was placed in a sealed container (diameter 8 cm × 4 cm) together with about 30 adult whitefly whitefly and allowed to stand in a thermostatic chamber (16 hours light period-8 hours dark period) at 25 ° C. The insects were observed for viability 6 days after release, and the mortality was calculated according to the following formula. The results were as shown in Table 39.
Death rate (%) = {Number of dead insects / (Number of living insects tens of dead insects)} × 100

Moreover, the theoretical value when there is no synergistic effect was calculated by the following Colby equation. The results were as shown in Table 40.
Colby's formula: Theoretical value (%) = 100− (A × B) / 100
(A: 100- (Dead rate when only Compound A is applied); B: 100- (Death rate when only Compound B is applied))

  The actual measured values of the mortality shown in Table 39 are clearly higher than the theoretical values shown in Table 40. Therefore, the combination of the compound of formula (I) and the drug shown in Table 39 has a synergistic effect. It was demonstrated to show.

Test Example 4: Tobacco whitefly adult control test A leaf disc having a diameter of 8 cm was cut out from a cucumber cultivated in a pot and placed on a damp absorbent cotton with the back of the leaf facing up. To this, the composition of the present invention prepared so that the compound 120 shown in Table 5 and other insecticides had the predetermined concentrations shown in Table 41 was added with 50% aqueous acetone (added with 0.33% new gramine). A diluted test solution or a chemical solution diluted with 50% acetone water (adding 0.33% new gramine) so as to have a predetermined concentration of each drug was sprayed. After air drying, this was placed in a sealed container (diameter 8 cm × 4 cm) together with about 30 adult whitefly whitefly and allowed to stand in a thermostatic chamber (16 hours light period-8 hours dark period) at 25 ° C. Two days after the release, the mortality of the insects was observed, and the death rate was calculated according to the following formula. The results were as shown in Table 41 and.
Death rate (%) = {Number of dead insects / (Number of living insects tens of dead insects)} × 100

Moreover, the theoretical value when there is no synergistic effect was calculated by the following Colby equation. The results were as shown in Tables 43 and 44.
Colby's formula: Theoretical value (%) = 100− (A × B) / 100
(A: 100- (Dead rate when only Compound A is applied); B: 100- (Death rate when only Compound B is applied))

  The measured values of mortality shown in Tables 41 and 42 are clearly higher than the theoretical values shown in Tables 43 and 44, and thus the compounds of formula (I) and the drugs shown in Tables 41 and 42 It was proved that the combination with shows a synergistic effect.

Claims (6)

2-ethyl-3,7-dimethyl-6- (4- (trifluoromethoxy) phenoxy) quinolin-4-yl methyl carbonate, or at least one of its agriculturally and horticulturally acceptable salts, and other pests A pest control composition comprising at least one control agent as an active ingredient, wherein the other pest control agent is an insecticide, and the insecticide includes diazinon, methomyl ), Cartap, cypermethrin, flufenoxuron, acequinocyl, imidacloprid, chlorfenapyr, spinosad, pymetroradine, pymetrozine, toy And emamectin benzoate, etofenprox, permethr in), flubendiamide, bifenazate, etiprole, indoxacarb, pyridalyl, milbemectin, quinomethionate, acrinathrin, acephate A composition selected from the group consisting of thiocyclam .   The composition according to claim 1, further comprising an agriculturally and horticulturally acceptable carrier.   The composition according to claim 1, which is in the form of a wettable powder, granular wettable powder, flowable powder, emulsion, powder, DL powder, fine granule F, granule, microcapsule or emulsion.   A pest comprising applying the pest control composition according to any one of claims 1 to 3 to a target pest, a target useful plant, a seed of the target useful plant, soil, or a cultivation carrier. How to protect useful plants from. 2-ethyl-3,7-dimethyl-6- (4- (trifluoromethoxy) phenoxy) quinolin-4-yl methyl carbonate, or at least one of its agriculturally and horticulturally acceptable salts, and other pests A combination with at least one control agent, wherein the other pesticide is an insecticide, said insecticide being diazinon, metomyl, cartap, cypermethrin ), Flufenoxuron, acequinocyl, imidacloprid, chlorfenapyr, spinosad, pymetrozine, tolfenpyrad, and benzoic benzoate Fenprox, permethrin, flubendiamide, Bifenazate, ethiprole, indoxacarb, pyridalyl, milbemectin, quinomethionate, acrinathrin, acephate, thiocyclam A combination that is to be selected . A method for protecting useful plants from pests,
2-ethyl-3,7-dimethyl-6- (4- (trifluoromethoxy) phenoxy) quinolin-4-yl methyl carbonate, or at least one of its agriculturally and horticulturally acceptable salts, and other pests Applying at least one of the control agents, simultaneously or separately, to the target pest, the target useful plant, the seed of the target useful plant, the soil or the cultivation carrier, wherein the other pest control agent is an insecticide. And the insecticide is diazinon, methomyl, cartap, cypermethrin, flufenoxuron, acequinocyl, imidacloprid, chlorfenapyr , Spinosad, pymetrozine, tolfenpyrad, and emamectin benzoate (emamec) tin benzoate, etofenprox, permethrin, flubendiamide, bifenazate, ethiprole, indoxacarb, pyridalyl, milbemectin, quinomethionate (Quinomethionate), acrinathrin, acephate, thiocyclam, a method selected from the group consisting of thiocyclam .