JP2003206281A - Acrylonitrile compound - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new agrochemical and an aquatic life attachment preventing agent, especially an insecticide and acaricide. <P>SOLUTION: This acrylonitrile compound is represented by formula (1) [wherein, X and Y are each independently H, a halogen, a 1-4C alkyl or a 1-4C haloalkyl; B is a 2-6C alkenyl, a 2-6C haloalkenyl, a 2-6C alkynyl or the like; and R is H, a halogen, a 1-6C alkyl or the like]. The agrochemical and the aquatic life attachment preventing agent containing the compound are provided. <P>COPYRIGHT: (C)2003,JPO

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel acrylonitrile compound and an agrochemical and an aquatic organism adhesion preventing agent containing the compound as an active ingredient. The pesticides in the present invention include insecticides, acaricides, nematicides, herbicides and fungicides, and particularly agricultural and horticultural, livestock, sanitary insecticides, acaricides and nematicides. .

[0002]

2. Description of the Related Art Regarding acrylonitrile derivatives as agricultural chemicals, WO97 / 40009 and WO99 / 449
93.

[0003]

With the long-term use of insecticides and fungicides, pests have acquired resistance in recent years,
Controlling with conventional insecticides and fungicides has become difficult.
Therefore, an object of the present invention is to provide a novel insecticide or fungicide that exhibits excellent pest control activity.

Further, in order to prevent the adhesion and reproduction of aquatic organisms in the sea and fresh water, an antifouling paint containing an organic tin compound such as bistributyltin oxide and a copper compound such as copper sulfate and cuprous oxide is used. There is. However, although organic tin compounds are effective in preventing the attachment of aquatic organisms, they are highly toxic, and in particular, the accumulation of fish and shellfish in the body is significant, which promotes environmental pollution and is currently subject to regulation. Copper compounds are widely used in antifouling paints for intake channels and ship bottoms, but because they contain copper, which is a heavy metal like tin compounds, there is concern about future environmental pollution, and favorable adhesion of aquatic organisms It is not possible to say that it is an inhibitor, and an aquatic organism adhesion inhibitor with less impact on the ecosystem and less secondary pollution is desired.

[0005]

Means for Solving the Problems As a result of continuous research to solve the above problems, the present inventors have found that the following compounds show excellent pest control activity and aquatic organism adhesion prevention activity. Heading The present invention has been completed.

That is, the present invention relates to the compounds [1] to [4] below (hereinafter referred to as the compounds of the present invention), pesticides containing the compounds described in [5] below as active ingredients, and the following [a]: [6] The present invention relates to an aquatic organism adhesion preventing agent containing the compound as an active ingredient.

[1] Formula (1):

[0008]

[Chemical 2]

[In the formula, X and Y are independently H and H
Rogen, C₁~ C_FourAlkyl or C₁~ C_FourHaloalkyl
And B is C₂~ C₆Alkenyl, C₂~ C₆Halo al
Kenil, C₂~ C₆Alkynyl, C₂~ C₆Halo alkini
R, C (O) Rf or C (S) Rg, R is H,
Halogen, C₁~ C₆Alkyl, C substituted with Rb₁~
C_FourAlkyl, C₁~ C_FourHaloalkyl, C₁~ C_FourArchi
C optionally substituted with₃~ C₇Cycloalkyl, C
₁~ C_FourC optionally substituted with alkyl₃~ C₇Haroshi
Croalkyl, C₁~ C₆Alkoxy, C₂~ C_FourArcheni
Roxy, C₂~ C_FourHaloalkenyloxy, C₂~ C_FourA
Lucinyloxy, C₁~ C_FourHaloalkoxy, C₁~ C_FourA
Rukylsulphenyl, C₁~ C_FourAlkylsulfinyl,
C₁~ C_FourAlkylsulfonyl, C₂~ C_FourAlkenyl sul
Phenyl, C₂~ C_FourAlkenylsulfinyl, C ₂~ C_Four
Alkenylsulfonyl, C₂~ C_FourAlkynylsulfeni
Le, C₂~ C_FourAlkynylsulfinyl, C₂~ C_FourArchi
Nylsulfonyl, C₁~ C_FourHaloalkylsulfenyl,
C₁~ C_FourHaloalkylsulfinyl, C₁~ C_FourHalo al
Killsulfonyl, C₂~ C_FourHaloalkenylsulfeni
Le, C₂~ C_FourHaloalkenylsulfinyl, C₂~ C_FourHa
Ralkenylsulfonyl, CN, NO₂, -NU¹U², Na
Futyl, methoxy substituted with Rb, C₂~ C_FiveArcoki
Sicarbonyl, C₂~ C_FourAlkoxyalkyl, C₂~ C_Four
Alkylcarbonyl, C₂~ C_FourHaloalkylcarboni
Le, C₂~ C_FiveAlkylcarbonyloxy, C₂~ C_FiveHalo
Alkylcarbonyloxy, C₃~ C₇Dialkylamino
Carbonyloxy, phenyl optionally substituted with Z
Phenoxy, optionally substituted with Z, substituted with Z
Optionally substituted benzoyl, optionally substituted with Z
Pyridyl, pyridyloxy optionally substituted with Z,
Thienyl optionally substituted with Z, adjacent substitution positions
Methylenedioxy bound at, bound at adjacent substitution positions
Halomethylenedioxy and -N = CT²T³Or inside
1 to 4 substituents selected from or adjacent substitutions
5 not formed by alkylene groups attached in position
Is an 8-membered ring, Z is independently halogen, C₁
~ C_FourAlkyl, C₁~ C_FourHaloalkyl, C₁~ C_FourAl
Coxy, C₁~ C_FourHaloalkoxy, C₁~ C_FourAlkyls
Luphenyl, C₁~ C_FourAlkylsulfinyl, C₁~ C_Four
Alkylsulfonyl, C₁~ C_FourHaloalkylsulfeni
Le, C₁~ C_FourHaloalkylsulfinyl, C₁~ C_FourHalo
Alkylsulfonyl, NO₂, CN, -NU¹U²And C₂
~ C_Five1 arbitrarily selected from alkoxycarbonyl
To 5 substituents, Rb is halogen, C₁~ C
_FourAlkyl and C₁~ C_FourOne selected from alkoxy
Phenyl which may be substituted with the above substituents,
Rf is C₂~ C₆Alkynyl or SRh, Rg
Is C₁~ C₆Alkyl, C₂~ C₆Alkenyl, C₂~ C₆
Alkynyl, C₁~ C₆Alkoxy, C₂~ C₆Alkenyl
Oxy, C₂~ C₆Alkynyloxy, C₁~ C₆Alkyl
Sulfenyl, C₂~ C₆Alkenylsulfenyl, C₂
~ C₆Alkynylsulfenyl, C₁~ C_FourSet with alkyl
C that may be replaced₃~ C₇Cycloalkyl, C₁~ C_Four
C optionally substituted with alkyl₃~ C₇Cycloalk
Roxy, C₁~ C_FourC optionally substituted with alkyl
₃~ C₇Cycloalkylsulfenyl, substituted with Z
Optionally phenyl, phenoxy optionally substituted with Z
Si, phenylsulfenyl optionally substituted with Z,
Benzyl optionally substituted with Z, optionally substituted with Z
Optionally benzyloxy, optionally substituted with Z
Benzyl sulfenyl, pyridyl, pyridyloxy, pyri
Dilsulphenyl, pyrazolyl, pyrazolyloxy or
Is pyrazolyl sulphenyl and Rh is C₁~ C₆A
Rukiru, C₂~ C₆Alkenyl, C₂~ C₆Alkynyl, C
₁~ C_FourC optionally substituted with alkyl₃~ C₇Cyclo
Alkyl, benzyl optionally substituted with Z, pyridinium
Or pyrazolyl, T²And T³Are each independent
To H, phenyl, benzyl or C₁~ C₆In alkyl
Yes or T²And T³And the carbon atom that is bonded to
May together form a 5- to 8-membered ring, U¹And U²Is
Independently H and C₁~ C₆Alkyl, C₂~ C_FourAlkyl
Represents or represents carbonyl, phenyl or benzyl
Is U¹And U²5 to 8 together with the carbon atom to which and are bound
You may form a member ring. ] Acrylonitrile represented by
Compound.

[2] R is H, halogen, C₁~ C₆Al
Kill, C replaced with Rb₁~ C_FourAlkyl, C₁~ C_FourHa
Lower alkyl, C₁~ C_FourOptionally substituted with alkyl
C ₃~ C₇Cycloalkyl, C₁~ C₆Alkoxy, C₁~
C_FourHaloalkoxy, -NU¹U², Metho substituted with Rb
Kish, C₂~ C_FiveAlkoxycarbonyl, C₂~ C_FourArco
Xyalkyl, C₂~ C_FourAlkylcarbonyl, C₂~ C_Four
Haloalkylcarbonyl, C₂~ C_FiveAlkyl carbonyl
Oxy, C₂~ C_FiveHaloalkylcarbonyloxy and Z
1 selected from phenyl that may be substituted with
Is four substituents, B is C (O) Rf or C
(S) Rg, Rf is SRh, Rg is C₁~
C₆Alkyl, C₂~ C₆Alkenyl, C₂~ C₆Alkini
Le, C₁~ C₆Alkoxy, C₂~ C₆Alkenyloxy,
C₂~ C₆Alkynyloxy, C₁~ C₆Alkyl sulfe
Nil, C₂~ C₆Alkenylsulfenyl, C₂~ C₆Al
Quinylsulfenyl, C₁~ C_FourSubstituted with alkyl
May be C₃~ C₇Cycloalkyl, C₁~ C_FourIn alkyl
C which may be substituted₃~ C₇Cycloalkyloxy,
C₁~ C_FourC optionally substituted with alkyl₃~ C₇Shiku
Roalkylsulfenyl, optionally substituted with Z
Phenyl, optionally substituted with Z, phenoxy, substituted with Z
Optionally substituted phenylsulphenyl, substituted with Z
Optionally substituted benzyl, optionally substituted with Z
Benzyl optionally substituted with benzyloxy or Z
Is sulfenyl, Rh is C₁~ C₆Alkyl, C₂~
C₆Alkenyl, C₂~ C₆Alkynyl, C₁~ C_FourArchi
C optionally substituted with₃~ C₇Cycloalkyl
Is benzyl optionally substituted with Z [1]
The acrylonitrile compound described.

[3] R is H, halogen, C₁~ C₆A
Rukiru, C₁~ C_FourHaloalkyl, C ₁~ C_FourSet with alkyl
C that may be replaced₃~ C₇Cycloalkyl, C₁~ C₆
Alkoxy, C₁~ C_FourSubstituted with haloalkoxy and Z
1 to 4 selected from phenyl which may be
Is a substituent, Rg is C₁~ C₆Alkyl, C₁~ C₆A
Lucoxy, C₁~ C₆Alkylsulfenyl, substituted with Z
Optionally substituted phenyl, optionally substituted by Z
Phenylsulfur optionally substituted with enoxy or Z
Is phenyl and Rh is C₁~ C₆The above being alkyl
The acrylonitrile compound according to [2].

[4] R is 1 to 4 substituents selected from halogen, C ₁ -C ₆ alkyl and C ₁ -C ₄ haloalkyl, Rg is phenoxy and Rh
Is methyl or ethyl, the acrylonitrile compound according to the above [3].

[5] An agrochemical characterized by containing, as an active ingredient, one or more acrylonitrile compounds described in [1] to [4] above.

[6] An aquatic organism adhesion preventing agent comprising one or more acrylonitrile compounds described in [1] to [4] above as an active ingredient.

[0015]

BEST MODE FOR CARRYING OUT THE INVENTION The compound (1) of the present invention, -C (C
The N) = C (OB)-moiety has two isomers, an E isomer and a Z isomer, both of which are included in the present invention.

The compounds having an asymmetric carbon atom among the compounds included in the present invention include optically active compounds (+) and (−).

Next, R, B, X, Y, Z, Rb, Rf, R
The preferable range of g, Rh, T ² , T ³ , U ¹ or U ² will be described.

The preferred range of R is the following groups. That is, RI: H, halogen, C₁~ C₆Alkyl, with Rb
The substituted C₁~ C_FourAlkyl, C₁~ C_FourHaloalkyl,
C₁~ C_FourC optionally substituted with alkyl₃~ C₇Shiku
Lower alkyl, C₁~ C₆Alkoxy, C₁~ C_FourHalo arco
Kisshi, -NU¹U², Methoxy substituted with Rb, C₂~ C_Five
Alkoxycarbonyl, C₂~ C_FourAlkoxyalkyl,
C₂~ C_FourAlkylcarbonyl, C₂~ C_FourHaloalkyl mosquito
Lubonyl, C₂~ C_FiveAlkylcarbonyloxy, C₂~
C_FiveSubstituted with haloalkylcarbonyloxy and Z
1 to 4 units selected from phenyl
Substitute. RII: H, halogen, C₁~ C₆Alkyl, C₁~ C_FourHalo
Alkyl, C₁~ C_FourC optionally substituted with alkyl
₃~ C₇Cycloalkyl, C₁~ C₆Alkoxy, C ₁~ C_Four
Phenyl optionally substituted with haloalkoxy and Z
1 to 4 substituents selected from RIII: halogen, C₁~ C₆Alkyl and C₁~ C_FourHalo
1 to 4 substituents selected from alkyl.

The preferred range of B is the following groups. That, BI: C ₂ ~C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ alkynyl, C ₂ -C ₆ haloalkynyl,
C (O) Rf, C (S) Rg BII: C (O) Rf, C (S) Rg Preferred X ranges are the following groups. That, XI: H, halogen and C ₁ -C ₄ alkyl. XII: halogen and C ₁ -C ₄ alkyl.

The preferred range of Y is the following groups. That is, YI: halogen, C ₁ -C ₄ alkyl and C ₁ -C ₄
Haloalkyl. YII: halogen and C ₁ -C ₄ alkyl.

Preferred Z ranges are the following groups. That is, ZI: 1 to 3 substituents selected from halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy. ZII: 1 or 2 substituents selected from halogen and C ₁ -C ₄ alkyl.

The preferred range of Rb is the following group. That is, RbI: phenyl optionally substituted with halogen or C ₁ -C ₄ alkyl.

The preferred range of Rf is the following group. In other words, RfI: C ₂ ~C ₆ alkynyl, SRh. RfII: SRh.

The preferred range of Rg is the following groups.
It That is, RgI: C₁~ C₆Alkyl, C₂~ C₆Alkenyl,
C₂~ C₆Alkynyl, C ₁~ C₆Alkoxy, C₂~ C₆A
Lucenyloxy, C₂~ C₆Alkynyloxy, C ₁~ C₆
Alkylsulfenyl, C₂~ C₆Alkenylsulfeni
Le, C₂~ C₆Alkynylsulfenyl, C₁~ C_FourArchi
C optionally substituted with₃~ C₇Cycloalkyl, C
₁~ C_FourC optionally substituted with alkyl₃~ C₇Cyclo
Alkyloxy, C₁~ C_FourEven if it is substituted with alkyl
Good C₃~ C₇Cycloalkylsulfenyl, substituted with Z
Optionally substituted phenyl, optionally substituted by Z
Enoxy, phenylsulfe optionally substituted by Z
Nyl, benzyl optionally substituted with Z, substituted with Z
Optionally substituted benzyloxy, optionally substituted with Z
Good benzylsulfenyl. RgII: C₁~ C₆Alkyl, C₁~ C₆Alkoxy, C₁~
C₆Alkylsulfenyl, optionally substituted with Z
Phenyl, phenoxy optionally substituted with Z or
Phenylsulfenyl optionally substituted with Z. RgIII: phenoxy.

The preferred range of Rh is the following groups:
It That is, RhI: C₁~ C₆Alkyl, C₂~ C₆Alkenyl,
C₂~ C₆Alkynyl, C ₁~ C_FourSubstituted with alkyl
May be C₃~ C₇Cycloalkyl, substituted with Z
Good benzyl. RhII: C₁~ C₆Alkyl. RhIII: methyl or ethyl.

The preferred T ² ranges are the following groups. That is, it may be T ² I: H, phenyl, benzyl or C ₁ -C ₆ alkyl, or may form a 5- or 6-membered ring with the carbon atom to which T ² and T ³ are bonded.

Preferred T³The range of
It That is, T³I: Phenyl, benzyl or C₁~ C₆Archi
Or T ²And T³The carbon source to which is bound
A 5- or 6-membered ring may be formed with the child.

The preferred U ¹ ranges are the following groups. That is, U ¹ I: H, C ₁ -C ₆ alkyl or C ₂ -C ₄ alkylcarbonyl, or forming a 5- to 7-membered ring with the carbon atom to which U ¹ and U ² are bonded. Good.

The preferred U ² ranges are the following groups. That is, U ² I is H, C ₁ -C ₆ alkyl or C ₂ -C ₄ alkylcarbonyl, or forms a 5- to 7-membered ring with the carbon atom to which U ¹ and U ² are bonded. Good.

Each group in the range of the above-mentioned preferable substituents can be arbitrarily combined with each other, and the particularly preferable range of the compound of the present invention is shown below.

That is, the preferred range of substituents is RI, BI,
XI, YI, ZI, RbI, RfI, RgI, RhI, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The preferred range of substituents is RI, BI, XI,
YI, ZI, RbI, RfI, RgI, RhII, T ² I, T ³ I, U ¹
The compounds of the present invention which are I and U ² I.

The preferred range of substituents is RI, BI, XI,
YI, ZI, RbI, RfI, RgI, RhIII, T ² I, T ³ I, U
^The compounds of the present invention which are ¹ I and U ² I.

The preferred range of substituents is RI, BI, XI,
YI, ZI, RbI, RfI, RgII, RhI, T ² I, T ³ I, U ¹
The compounds of the present invention which are I and U ² I.

The preferred range of substituents is RI, BI, XI,
YI, ZI, RbI, RfI, RgII, RhII, T ² I, T ³ I, U
^The compounds of the present invention which are ¹ I and U ² I.

The preferred range of substituents is RI, BI, XI,
YI, ZI, RbI, RfII, RgII, RhII, T ² I, T ³ I,
The compound of the present invention which is U ¹ I or U ² I.

Preferred substituent ranges are RI, BI, XI,
YI, ZI, RbI, RfII, RgIII, RhII, T ² I, T ³ I,
The compound of the present invention which is U ¹ I or U ² I.

Preferred substituent ranges are RI, BI, XI,
YI, ZI, RbI, RfII, RgIII, RhIII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

Preferred substituent ranges are RII, BI, XI,
YI, ZI, RbI, RfI, RgI, RhI, T ² I, T ³ I, U
^The compounds of the present invention which are ¹ I and U ² I.

Preferred substituent ranges are RII, BI, XI,
YI, ZI, RbI, RfI, RgI, RhII, T ² I, T ³ I, U ¹
The compounds of the present invention which are I and U ² I.

Preferred substituent ranges are RII, BI, XI,
YI, ZI, RbI, RfI, RgI, RhIII, T ² I, T ³ I, U
^The compounds of the present invention which are ¹ I and U ² I.

Preferred substituent ranges are RII, BI, XI,
YI, ZI, RbI, RfI, RgII, RhI, T ² I, T ³ I, U ¹
The compounds of the present invention which are I and U ² I.

Preferred substituent ranges are RII, BI, XI,
YI, ZI, RbI, RfI, RgII, RhII, T ² I, T ³ I, U
^The compounds of the present invention which are ¹ I and U ² I.

Preferred substituent ranges are RII, BI, XI,
YI, ZI, RbI, RfII, RgII, RhII, T ² I, T ³ I,
The compound of the present invention which is U ¹ I or U ² I.

Preferred substituent ranges are RII, BI, XI,
YI, ZI, RbI, RfII, RgIII, RhII, T ² I, T ³ I,
The compound of the present invention which is U ¹ I or U ² I.

Preferred substituent ranges are RII, BI, XI,
YI, ZI, RbI, RfII, RgIII, RhIII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The preferred range of substituents is RII, BII, X
I, YI, ZI, RbI, RfI, RgI, RhI, T ² I, T ³ I,
The compound of the present invention which is U ¹ I or U ² I.

The range of preferred substituents is RII, BII, X
I, YI, ZI, RbI, RfI, RgI, RhII, T ² I, T ³ I,
The compound of the present invention which is U ¹ I or U ² I.

The preferred range of substituents is RII, BII, X
I, YI, ZI, RbI, RfI, RgI, RhIII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The preferred range of substituents is RII, BII, X
I, YI, ZI, RbI, RfI, RgII, RhI, T ² I, T ³ I,
The compound of the present invention which is U ¹ I or U ² I.

The preferred range of substituents is RII, BII, X
I, YI, ZI, RbI, RfI, RgII, RhII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The preferred range of substituents is RII, BII, X
I, YI, ZI, RbI, RfII, RgII, RhII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The range of preferred substituents is RII, BII, X
I, YI, ZI, RbI, RfII, RgIII, RhII, T ² I, T ³
The compound of the present invention which is I, U ¹ I or U ² I.

The preferred range of substituents is RII, BII, X
I, YI, ZI, RbI, RfII, RgIII, RhIII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The preferred range of substituents is RII, BII, XI
I, YI, ZI, RbI, RfI, RgI, RhI, T ² I, T ³ I,
The compound of the present invention which is U ¹ I or U ² I.

The preferred range of substituents is RII, BII, XI
I, YI, ZI, RbI, RfI, RgI, RhII, T ² I, T ³ I,
The compound of the present invention which is U ¹ I or U ² I.

The preferred range of substituents is RII, BII, XI
I, YI, ZI, RbI, RfI, RgI, RhIII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The preferred range of substituents is RII, BII, XI
I, YI, ZI, RbI, RfI, RgII, RhI, T ² I, T ³ I,
The compound of the present invention which is U ¹ I or U ² I.

The preferred range of substituents is RII, BII, XI
I, YI, ZI, RbI, RfI, RgII, RhII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The preferred range of substituents is RII, BII, XI
I, YI, ZI, RbI, RfII, RgII, RhII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The preferred range of substituents is RII, BII, XI
I, YI, ZI, RbI, RfII, RgIII, RhII, T ² I, T ³
The compound of the present invention which is I, U ¹ I or U ² I.

The preferred range of substituents is RII, BII, XI
I, YI, ZI, RbI, RfII, RgIII, RhIII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The preferred range of substituents is RII, BII, XI
I, YII, ZI, RbI, RfI, RgI, RhI, T ² I, T ³ I,
The compound of the present invention which is U ¹ I or U ² I.

The preferred range of substituents is RII, BII, XI
I, YII, ZI, RbI, RfI, RgI, RhII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The preferred range of substituents is RII, BII, XI
I, YII, ZI, RbI, RfI, RgI, RhIII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The preferred range of substituents is RII, BII, XI
I, YII, ZI, RbI, RfI, RgII, RhI, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The range of preferred substituents is RII, BII, XI
I, YII, ZI, RbI, RfI, RgII, RhII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The range of preferred substituents is RII, BII, XI.
I, YII, ZI, RbI, RfII, RgII, RhII, T ² I, T ³
The compound of the present invention which is I, U ¹ I or U ² I.

The preferred range of substituents is RII, BII, XI
I, YII, ZI, RbI, RfII, RgIII, RhII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The preferred range of substituents is RII, BII, XI
I, YII, ZI, RbI, RfII, RgIII, RhIII, T ² I,
The compound of the present invention which is T ³ I, U ¹ I or U ² I.

The preferred range of substituents is RII, BII, XI
I, YII, ZII, RbI, RfI, RgI, RhI, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The range of preferred substituents is RII, BII, XI.
I, YII, ZII, RbI, RfI, RgI, RhII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The preferred range of substituents is RII, BII, XI
I, YII, ZII, RbI, RfI, RgI, RhIII, T ² I, T ³
The compound of the present invention which is I, U ¹ I or U ² I.

The preferred range of substituents is RII, BII, XI
I, YII, ZII, RbI, RfI, RgII, RhI, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The preferred range of substituents is RII, BII, XI
I, YII, ZII, RbI, RfI, RgII, RhII, T ² I, T ³
The compound of the present invention which is I, U ¹ I or U ² I.

The preferred range of substituents is RII, BII, XI
I, YII, ZII, RbI, RfII, RgII, RhII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The preferred range of substituents is RII, BII, XI
I, YII, ZII, RbI, RfII, RgIII, RhII, T ² I,
The compound of the present invention which is T ³ I, U ¹ I or U ² I.

The range of preferred substituents is RII, BII, XI
I, YII, ZII, RbI, RfII, RgIII, RhIII, T ² I,
The compound of the present invention which is T ³ I, U ¹ I or U ² I.

The preferred range of substituents is RIII, BI, X
I, YI, ZI, RbI, RfI, RgI, RhI, T ² I, T ³ I,
The compound of the present invention which is U ¹ I or U ² I.

The preferred range of substituents is RIII, BI, X
I, YI, ZI, RbI, RfI, RgI, RhII, T ² I, T ³ I,
The compound of the present invention which is U ¹ I or U ² I.

The range of preferred substituents is RIII, BI, X
I, YI, ZI, RbI, RfI, RgI, RhIII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BI, X
I, YI, ZI, RbI, RfI, RgII, RhI, T ² I, T ³ I,
The compound of the present invention which is U ¹ I or U ² I.

The range of preferred substituents is RIII, BI, X
I, YI, ZI, RbI, RfI, RgII, RhII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BI, X
I, YI, ZI, RbI, RfII, RgII, RhII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BI, X
I, YI, ZI, RbI, RfII, RgIII, RhII, T ² I, T ³
The compound of the present invention which is I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BI, X
I, YI, ZI, RbI, RfII, RgIII, RhIII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, X
I, YI, ZI, RbI, RfI, RgI, RhI, T ² I, T ³ I,
The compound of the present invention which is U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, X
I, YI, ZI, RbI, RfI, RgI, RhII, T ² I, T ³ I,
The compound of the present invention which is U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, X
I, YI, ZI, RbI, RfI, RgI, RhIII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The preferred range of substituents is RIII, BII, X
I, YI, ZI, RbI, RfI, RgII, RhI, T ² I, T ³ I,
The compound of the present invention which is U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, X
I, YI, ZI, RbI, RfI, RgII, RhII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The preferred range of substituents is RIII, BII, X
I, YI, ZI, RbI, RfII, RgII, RhII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The preferred range of substituents is RIII, BII, X
I, YI, ZI, RbI, RfII, RgIII, RhII, T ² I, T ³
The compound of the present invention which is I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, X
I, YI, ZI, RbI, RfII, RgIII, RhIII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI.
I, YI, ZI, RbI, RfI, RgI, RhI, T ² I, T ³ I,
The compound of the present invention which is U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI.
I, YI, ZI, RbI, RfI, RgI, RhII, T ² I, T ³ I,
The compound of the present invention which is U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI.
I, YI, ZI, RbI, RfI, RgI, RhIII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI.
I, YI, ZI, RbI, RfI, RgII, RhI, T ² I, T ³ I,
The compound of the present invention which is U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI.
I, YI, ZI, RbI, RfI, RgII, RhII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI.
I, YI, ZI, RbI, RfII, RgII, RhII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI.
I, YI, ZI, RbI, RfII, RgIII, RhII, T ² I, T ³
The compound of the present invention which is I, U ¹ I or U ² I.

The preferred range of substituents is RIII, BII, XI
I, YI, ZI, RbI, RfII, RgIII, RhIII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI.
I, YII, ZI, RbI, RfI, RgI, RhI, T ² I, T ³ I,
The compound of the present invention which is U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI.
I, YII, ZI, RbI, RfI, RgI, RhII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI.
I, YII, ZI, RbI, RfI, RgI, RhIII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI.
I, YII, ZI, RbI, RfI, RgII, RhI, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI.
I, YII, ZI, RbI, RfI, RgII, RhII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI.
I, YII, ZI, RbI, RfII, RgII, RhII, T ² I, T ³
The compound of the present invention which is I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI.
I, YII, ZI, RbI, RfII, RgIII, RhII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI.
I, YII, ZI, RbI, RfII, RgIII, RhIII, T ² I,
The compound of the present invention which is T ³ I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI.
I, YII, ZII, RbI, RfI, RgI, RhI, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI.
I, YII, ZII, RbI, RfI, RgI, RhII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI
I, YII, ZII, RbI, RfI, RgI, RhIII, T ² I, T ³
The compound of the present invention which is I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI.
I, YII, ZII, RbI, RfI, RgII, RhI, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI.
I, YII, ZII, RbI, RfI, RgII, RhII, T ² I, T ³
The compound of the present invention which is I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI.
I, YII, ZII, RbI, RfII, RgII, RhII, T ² I, T
^The compound of the present invention which is ³ I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI.
I, YII, ZII, RbI, RfII, RgIII, RhII, T ² I,
The compound of the present invention which is T ³ I, U ¹ I or U ² I.

The range of preferred substituents is RIII, BII, XI.
I, YII, ZII, RbI, RfII, RgIII, RhIII, T ² I,
The compound of the present invention which is T ³ I, U ¹ I or U ² I.

Next, R, B, X, Y, Z, Rb, Rf, R
Examples of each atom and group in the definition of g, Rh, T ² , T ³ , U ¹ or U ² are shown.

Examples of the halogen atom in the definition of R, X, Y, Z and Rb include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a fluorine atom, a chlorine atom and a bromine atom.

R, X, Y, Z, Rb, Rg, Rh, T ² , T
Alkyl in the definition of ³ , U ¹ and U ² is, as linear or branched alkyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, te.
rt-butyl, sec-butyl, pentyl-1, pentyl-2, pentyl-3, 2-methylbutyl-1, 2-methylbutyl-2, 2-methylbutyl-3, 3-methylbutyl-1,2,2-dimethylpropyl -1, hexyl-
1, hexyl-2, hexyl-3, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl , 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,
1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl and the like are selected, and each is selected within the specified carbon number range. .

In the definition of R, X, Y and Z, haloalkyl includes fluoromethyl, chloromethyl, bromomethyl, fluoroethyl, chloroethyl, bromoethyl and fluoro-n as linear or branched haloalkyl.
-Propyl, chloro-n-propyl, difluoromethyl, chlorodifluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, difluoroethyl,
Examples thereof include trifluoroethyl, trichloroethyl, chlorodifluoromethyl, bromodifluoromethyl, trifluorochloroethyl, hexafluoro-n-propyl, chlorobutyl and fluorobutyl, and each is selected from the range of carbon number specified.

C ₃ -C ₇ cycloalkyl optionally substituted by C ₁ -C ₄ alkyl in the definition of R, Rg and Rh is cyclopropyl, 1-methylcyclopropyl, 2,2,3,3. , -Tetramethylcyclopropyl,
Examples thereof include cyclobutyl, 1-ethylcyclobutyl, 1-n-butylcyclobutyl, cyclopentyl, 1-methylcyclopentyl, cyclohexyl, 1-methylcyclohexyl and 4-methylcyclohexyl, cycloheptyl.

C ₃ -C ₇ halocycloalkyl optionally substituted with C ₁ -C ₄ alkyl in the definition of R is 2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2 -Dibromocyclopropyl, 2,2-difluoro-1-methylcyclopropyl,
2,2-dichloro-1-methylcyclopropyl, 2,2
-Dibromo-1-methylcyclopropyl, 2,2,3
3-tetrafluorocyclobutyl etc. are mentioned.

As alkenyloxy in the definition of R and Rg, C ₂ -C ₄ straight-chain or branched alkenyloxy is allyloxy, 2-propenyloxy, 2-
Examples thereof include butenyloxy and 2-methyl-2-propenyloxy.

The haloalkenyloxy in the definition of R includes 3-chloro-2-propenyloxy, 4-chloro-2-butenyloxy, 3,3-difluoro as C ₂ -C ₄ linear or branched haloalkenyloxy. -2-
Propenyloxy, 3,3-dichloro-2-propenyloxy, 2,3,3-trifluoro-2-propenyloxy, 4,4-dichloro-3-butenyloxy and 4,
4-difluoro-3-butenyloxy and the like can be mentioned.

Alkoxy in the definition of R, Z, Rb and Rg includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy as linear or branched alkoxy.
tert-butoxy, n-pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-
Ethylpropyloxy, n-hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,
1-dimethylbutyloxy, 1,2-dimethylbutyloxy, 1,3-dimethylbutyloxy, 2,2-dimethylbutyloxy group, 2,3-dimethylbutyloxy group,
3,3-dimethylbutyloxy, 1-ethylbutyloxy, 2-ethylbutyloxy, 1,1,2-trimethylpropyloxy, 1,2,2-trimethylpropyloxy, 1-ethyl-1-methylpropyloxy and 1-ethyl-2-methylpropyloxy and the like can be mentioned, and each is selected from the specified carbon number range.

C ₁ -C ₄ haloalkoxy in the definition of R and Z includes C ₁ -C ₄ linear or branched haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy and chloro. Difluoromethoxy, bromodifluoromethoxy, dichlorofluoromethoxy, chloromethoxy, dichloromethoxy, trichloromethoxy, bromomethoxy, fluoroethoxy, chloroethoxy, bromoethoxy, difluoroethoxy, trifluoroethoxy, tetrafluoroethoxy, pentafluoroethoxy, trichloroethoxy, Trifluorochloroethoxy, fluoropropoxy, chloropropoxy, bromopropoxy, fluorobutoxy, chlorobutoxy, fluoro-iso-propoxy and chloro-iso-propoxy. Kisshi and the like.

C ₁ -C ₄ alkylsulfenyl in the definition of R, Z and Rg includes methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, iso-butylthio, sec-butylthio and tert-butylthio. can give.

C ₁ -C ₄ alkylsulfinyl in the definition of R and Z includes methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, iso-propylsulfinyl, n-butylsulfinyl and iso-.
Butylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl and the like can be mentioned.

C ₁ -C ₄ alkylsulfonyl in the definition of R and Z includes methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, iso-propylsulfonyl, n-butylsulfonyl, iso-butylsulfonyl, sec-butylsulfonyl and Examples include tert-butylsulfonyl.

Alkoxyalkyl in the definition of R includes methoxymethyl, ethoxymethyl, n-propoxymethyl, i-propoxymethyl, n-butoxymethyl, i-butoxymethyl, s-butoxymethyl, t-butoxymethyl and n-butoxymethyl. Examples include pentyloxymethyl, methoxyethyl, ethoxymethyl, methoxypropyl, etc., each selected from the specified carbon number range.

The naphthyl in the definition of R includes 1-naphthyl and 2-naphthyl.

As haloalkylsulfenyl in the definition of R and Z, C ₁ -C ₄ linear or branched haloalkylthio includes fluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, trifluoromethylthio, trichloromethylthio, and 2 , 2,
Examples include 2, -trifluoroethylthio, 1,1,2,2, -tetrafluoroethylthio, fluoroethylthio, pentafluoroethylthio and fluoro-iso-propylthio groups.

Haloalkylsulfinyl in the definition of R and Z is C ₁ -C ₄ linear or branched haloalkylsulfinyl such as fluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, trifluoromethylsulfinyl and trichloro. Methylsulfinyl, 2,2
2, -trifluoroethylsulfinyl, 1,1,2,
2-tetrafluoroethylsulfinyl, fluoroethylsulfinyl, pentafluoroethylsulfinyl, fluoro-iso-propylsulfinyl and the like can be mentioned.

Haloalkylsulfonyl in the definition of R and Z is fluoromethylsulfonyl as C ₁ -C ₄ linear or branched haloalkylsulfonyl,
Chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2,2, -trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, fluoroethylsulfonyl, pentafluoro Examples thereof include ethylsulfonyl and fluoro-iso-propylsulfonyl.

C ₁ -C ₄ alkenyl in the definition of B, Rg and Rh is allyl, 2-propenyl, 2-butenyl, 2-methyl-2-propenyl, 4-methyl-3-.
Pentenyl, 2-hexenyl, etc. are mentioned, and each is selected with a designated carbon number.

The C ₃ -C ₇ cycloalkyloxy group which may be substituted by C ₁ -C ₄ alkyl in the definition of Rg is cyclopropoxy group, cyclobutoxy group, cyclopentoxy group, cyclohexyloxy group, 1 -Methylcyclopropoxy group and the like.

C ₁ -C substituted with R b in the definition of R
₄ alkyl includes benzyl, 2-chlorobenzyl,
3-bromobenzyl, 4-chlorobenzyl, 4-methylbenzyl, 4-tert-butylbenzyl, 1-phenylethyl, 1- (3-chlorophenyl) ethyl, 2-
Phenylethyl, 1-methyl-1-phenylethyl, 1
-(4-chlorophenyl) -1-methylethyl, 1-
(3-chlorophenyl) -1-methylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, 1-phenylbutyl, 2-phenylbutyl, 3
-Phenylbutyl, 4-phenylbutyl, 1-methyl-
1-phenylpropyl, 1-methyl-2-phenylpropyl, 1-methyl-3-phenylpropyl, 2-methyl-2-phenylpropyl, 2- (4-chlorophenyl)
Examples include 2-methyl-propyl and 2-methyl-2- (3-methylphenyl) propyl.

-NU ¹ U ² in the definition of R and Z is methylamino, ethylamino, n-propylamino,
Isopropylamino, n-butylamino, isobutylamino, sec-butylamino, tert-butylamino, n-pentylamino, 1-methylbutylamino, 2
-Methylbutylamino, 3-methylbutylamino, 1,
1-dimethylpropylamino, 1,2-dimethylpropylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, n-hexylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino , 4-methylpentylamino, 1,1-
Dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3
-Dimethylbutylamino, 1-ethylbutylamino, 2
-Ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino, 1
-Ethyl-1-methylpropylamino, dimethylamino, diethylamino, di-n-propylamino, diisopropylamino, di-n-butylamino, di-sec-butylamino, diisobutylamino, di-n-pentylamino, di- n-hexylamino, methylethylamino,
Methylpropylamino, methylisopropylamino, methylbutylamino, methyl-sec-butylamino, methylisobutylamino, methyl-tert-butylamino, methylpentylamino, methylhexylamino, ethylpropylamino, ethylisopropylamino, ethylbutylamino, Ethyl-sec-butylamino, ethylisobutylamino, ethylpentylamino, ethylhexylamino, phenylamino, benzylamino, N-
Methylacetamide, N-ethylacetamide and N-
Phenylacetamide N-acetylacetamide and the like can be mentioned, and each is selected within the specified carbon number range.

C ₂ -C ₅ alkoxycarbonyl in the definition of R and Z is methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, iso-propoxycarbonyl, n-butoxycarbonyl, sec-
Examples include butoxycarbonyl, iso-butoxycarbonyl and tert-butoxycarbonyl.

C ₂ -C ₄ alkylcarbonyl in the definition of R, U ¹ and U ² is acetyl, propionyl,
Butanoyl and iso-butanoyl groups.

Examples of C ₂ -C ₄ haloalkylcarbonyl in the definition of R include chloroacetyl, trifluoroacetyl, 3,3,3-trifluoropropionyl and pentafluoropropionyl groups.

Examples of C ₂ -C ₅ haloalkylcarbonyloxy in the definition of R include chloroacetyloxy, trifluoroacetyloxy, 3,3,3, -trifluoropropionyloxy and pentafluoropropionyloxy.

C ₃ -C ₇ dialkylaminocarbonyloxy in the definition of R includes dimethylaminocarbonyloxy, diethylaminocarbonyloxy and di-i.
-Propylaminocarbonyloxy and the like.

Pyridyl optionally substituted with Z in the definition of R is 2-pyridyl optionally substituted with Z, 3-pyridyl optionally substituted with Z and Z.
4-pyridyl optionally substituted with, preferably 2-pyridyl optionally substituted with Z and 2-pyridyl optionally substituted with Z, and more preferably substituted with Z. It may be 3-pyridyl.

Pyridyloxy optionally substituted by Z in the definition of R is 2-pyridyloxy optionally substituted by Z, 3-pyridyloxy optionally substituted by Z and substituted by Z. 4-pyridyloxy which may be present.

The thienyl optionally substituted by Z in the definition of R includes 2-thienyl optionally substituted by Z and 3-thienyl optionally substituted by Z.

In the definition of R, -N = CT ² T ³ means alkylideneamino, benzylideneamino, arylideneamino or cycloalkylideneamino, methylideneamino, ethylideneamino, propylideneamino, isopropylideneamino, 4-methyl-2. -Pentylidene amino, cyclopentylidene amino, cyclohexylidene amino and the like can be mentioned.

Rb-substituted methoxy in the definition of R is benzyloxy, 2-chlorobenzyloxy, 3-chlorobenzyloxy, 4-chlorobenzyloxy, 3-methylbenzyloxy, 4-t-butylbenzyloxy. , 2,6-difluorobenzyloxy, 2-fluoro-4-chlorobenzyloxy, 4-isopropoxybenzyloxy and the like.

Alkenylsulfenyl in the definition of R and Rg includes allylsulfenyl, 2-propenylsulfenyl, 2-butenylsphenyl and 2- as C ₂ -C ₄ straight or branched alkenylsulfenyl.
Methyl-2-propenylsulfenyl and the like can be mentioned.

Alkenylsulfinyl in the definition of R includes C ₂ -C ₄ straight-chain or branched alkenylsulfinyl as allylsulfinyl, 2-propenylsulfinyl, 2-butenylsphinyl and 2-methyl-
2-propenylsulfinyl etc. are mentioned.

Examples of the alkenylsulfonyl in the definition of R include C ₂ -C ₄ linear or branched alkenylsulfonyl, such as allylsulfonyl, 2-propenylsulfonyl, 2-butenylsulfonyl and 2-methyl-2-propenylsulfonyl. .

The haloalkenylsulfenyl in the definition of R includes 3-chloro-2-propenylsulfenyl and 4-chloro-2-butenylsulfenyl as C ₂ -C ₄ linear or branched haloalkenylsulfenyl. ,
3,3-dichloro-2-propenylsulfenyl, 4,
4-dichloro-3-butenylsulfenyl and 4,4-
Examples thereof include difluoro-3-butenylsulfenyl.

The haloalkenylsulfinyl in the definition of R includes 3-chloro-2-propenylsulfinyl, 3,2-dichloro-2-propenylsulfinyl and 4-as C ₂ -C ₄ linear or branched haloalkenylsulfinyl. Chloro-2-butenylsulfinyl, 4,
4-dichloro-3-butenylsulfinyl and 4,4-
Examples thereof include difluoro-3-butenylsulfinyl.

The haloalkenylsulfonyl in the definition of R includes 3-chloro-2-propenylsulfonyl, 3,3-dichloro-2-propenylsulfonyl as C ₂ -C ₄ linear or branched haloalkenylsulfonyl,
4-chloro-2-butenylsulfonyl, 4,4-dichloro-3-butenylsulfonyl and 4,4-difluoro-
3-butenylsulfonyl and the like can be mentioned.

Examples of C ₂ -C ₄ alkynyloxy in the definition of R include 2-propynyloxy, 2-butynyloxy, 1-methyl-2-propynyloxy and the like.

As C ₂ -C ₄ alkynylsulfenyl in the definition of R, 2-propynylsulfenyl, 2-
Examples include butynylsulfenyl and 1-methyl-2-propynylsulfenyl.

As C ₂ -C ₄ alkynylsulfinyl in the definition of R, 2-propynylsulfinyl, 2-
Examples include butynylsulfinyl and 1-methyl-2-propynylsulfinyl.

Examples of C ₂ -C ₄ alkynylsulfonyl in the definition of R include 2-propynylsulfonyl, 2-butynylsulfonyl, 1-methyl-2-propynylsulfonyl and the like.

The compounds of the present invention are so-called agricultural pests that harm agricultural and horticultural crops and trees, so-called livestock pests that parasitize livestock and poultry, so-called hygienic pests that have various adverse effects on human living environments such as houses, and warehouses. It is possible to effectively control so-called stored-grain pests that damage stored grains and the like, and any pests such as mites, nematodes, molluscs, and crustaceans that occur in similar situations at low concentrations.

Insects which can be controlled using the compounds of the present invention,
Specific examples of ticks, nematodes, molluscs and crustaceans include, but are not limited to:

Diamondback moth (Plutella xylostella), Tamanaga moth (Agrotis ipsilon), Cabbage moth (Agrotis segetum),
Helicoverpa armigera, Helicoverpa armigera
overpa assulta), cotton ball worm (Helicoverpa
zea), tobacco bad worms (Heliothis virescens), armyworms (Mamestra brassicae), and yellow-tailed moths (Naranga)
aenescens), Tamanaginuwawaba (Plusia nigrisigna),
Armyworm (Pseudaletiase parata), white armyworm (Spodoptera exigua), common earworm (Spodoptera l)
itura), cotton leaf worm (Spodoptera littorali
s), Fall Army Worm (Spodoptera frugiperd
a), Southern army worms (Spodoptera eridania), tobacco horn worms (Manduca sexta), grapeberry moss (Endopiza viteana), ginkgo worm moth (Lyonetia)
prunifoliella malinella), Kingfisher (Phyllonor)
ycter ringoneella), mandarin orange moth (Phyllocnistis)
citrella), cotton bollworm (Pectinophora gossypiell)
a), peach squid (Carposina niponensis), apple coconut beetle (Adoxophyes orana faciata), tea beetle beetle (Adoxophyes honmai), tea beetle (Homo)
na magnamina), codling moths (Cydla pomonella), nasihime moths (Grapholita molesta), nigga (Chilo s)
uppressalis), Cobb Nomeiga (Cnaphalocrocis medinali)
s), Hellula undalis, European corn borer (Ostrinia nubilalis), soybean looper (Pseudoplusia includens), nettle herb (Trichoplusia ni), American white-hit (Hyphantria)
cunea), Pieris rapae crucivora,
Lepidopteran pests such as Ichmon disseri (Parnara guttata),
Anemona cuprea, Anomala cuprea
la rufocuprea), Japanese beetle (Popillia japonica), Colorado potato beetle (Lepinotarsa decemlineata), kidney bean (Epilachna varivestis), beetle (Melanotus tamsuyensis), tobacco beetle
(Lasioderma serricorne), Himehiratakeshikisu (Epur
aea domina), Red-tailed Ladybird (Henosepilachna)
vigintioctopunctata), White rice beetle (Tenebrio molitor), Red-eye beetle (Tribolium c)
astaneum), stag beetle (Anoplophora malasiac)
a), Japanese pine beetle (Monochamus alternatus),
Azuki bean weevil (Callosobruchus chinensis), urchin beetle (Aulacophora femoralis), rice drool beetle (Oulema)
oryzae), Phyllotreta striolat
a), Weevil Weevil (Cylasformicarius), Weevil Weevil (Anthonomus grandis), Weevil (Ethinocne)
mus squameus), Alfalfa weevil (Hypera p
ostica), rice weevil (Lissorhoptrus oryzophilu)
s), elephants (Sitophilus zeamais), weevil weevil
(Sphenophrus venatus vestius), Granary Weeville (Sitophilus granarius), Southern Corn Rootworm
(Diabrotica undecimpunctata), Western corn rootworms (Diabrotica virgifera), Northern corn rootworms (Diabrotica barberi), Coleoptera pests such as Aoba arigata stag beetle (Paederus fuscipes), etc.
dema rugosa), the stink bug, Eysarcoris ventrali
s), hare stink bug (Halyomorpha mista), southern green stink bug (Nezara viridula), spider helicopter bug (Leptoc)
orisa chinensis), the Japanese bug, Riptortus clava
tus), the brown bug, Togo hemipteru
s), American bug bug (), azalea gumbai (S
tephanitis pyrioides), leafhopper leafhopper (Epiaca
nthus stramineus), Green leafhopper (Empoas)
ca onukii), potato leaf hopper (Empoasca fabae),
Black-necked leafhopper (Nephotettix cinctinceps), brownhopper plant (Laodelphax striatellus), brown planthopper (N
ilaparvata lugens), Seguro planta (Sogatella furcife)
ra), orange lice (Trioza erytreae), pear lice
(Psylla pyrisuga), Bemisia tabaci (Bemisia tabac)
i), silver leaf whitefly (Bemisia argentifoli)
i), orange whitefly (Dialeurodescitri), whitefly whitefly (Trialeurodes vaporariorum), cotton aphid (Aphis gossypii), snow beetle (Aphis pom)
i), green peach aphid (Myzus persicae), giant scale insect (Drosicha corpulenta), scale insect (Icerya purchasi), orange scale insect (Pl)
anococcus citri), scale insect (Pseudococcu)
s comstocki), ruby weevil (Ceroplastes rubens),
Japanese scale insect (Unaspis yanonensis), bed bug
(Cimex lectularius) and other hemiptera pests, orange thrips (Frankliniella occidentalis), thrips thrips (Frankliniella intonsa), teapot thrips (Scirtothrips dorsalis), southern thrips thrips, thrips thrips
Pests of the order Thysanoptera, such as citrus fruit fly (Dacus dorsalis), fruit fly (Dacus cucurbitae), and fruit fly (Cer
atitis capitata), rice leaf fly (Hydrellia g)
riseola), eggplant leaf fly (Liriomyza bryoniae), bean leaf fly (Liriomyza trifolii), fly fly (Hylem)
ya platura), Apple Maggot (Rhagoletis pomonell
a), Hessian fry (Mayetiola destructor), housefly
(Musca domestica), flies (Stomoxys calcitrans),
Sheep fruit fly (Melophagus ovinus), blue fly (Hypoderma lineatum), bull fly (Hypoderma bovi)
s), sheep flies (Oestrusovis), tsetse flies (Glossina)
palpalis, Glossina morsitans), Chiacio buyu (Pro
simulium yezoensis), cattle fly (Tabanus trigonus),
Blue Fly (Telmatoscopus albipunctatus), Tokunaganukaka (Leptoconops nipponensis), Culex pipiens (Cu)
lex pipiens pallens), Aedes albopic
utus), Aedes aegypti, Anopheles hyracanus sinesis and other dipterous pests, Apethymus kuri, Athalia ros
ae japonensis), pine bee (Neodiprion sertife)
r), Guntai Ali (Eciton burchelli, Eciton schmitt
i), Black-footed Ant (Camponotus japonicus), Vespa mandarina, Bulldog Ant (Myrmecia s)
pp.), Fire Ants (Solenopsis spp.), Pharaoh ant (Monomorium pharaonis), and other insect pests, Periplaneta fuliginosa, Yamato cockroach (P
eriplaneta japonica), German cockroach (Blattella g)
ermanica) and other insect pests such as Emerging crickets (Teleogryll)
us emma), kerula (Gryllotalpa africana), locust grasshopper (Locusta migratoria), coba neago (Oxya yezoensi)
s), Orchid grasshopper (Schistocerca gregaria) and other orthoptera insects, termites (Coptotermes formosanus),
Termite pests such as Yamato termites (Reticulitermes speratus) and Taiwanese termites (Odontotermes formosanus), cat fleas (Ctenocephalidae felis), human fleas (Pule
x irritans), Keopsuneminomi (Xenopsylla cheopi
s) and other isoptera pests, such as the golden-footed lice (Menacanthus)
stramineus), cattle lice (Bovicola bovis) and other pests of the order Lice, cattle lice (Haematopinus eurysternus),
Swine lice (Haematopinus suis), American lice (Lino
gnathus vituli), the white lice (Solenopotes capi)
Llatus) and other lice pests, citrus red mite (Panonychus c
itri), Apple spider mite (Panonychus ulmi), Kanzawa spider mite (Tetranychus kanzawai), Nami spider mite (Tetranychus u)
rticae) and other spider mites, Acaphylla
theae), citrus rust mite (Aculops pelekassi), mite mite (Eriophyes chibaensis), tulip rust mite (Aceria tulipae), and other mite dust mite (Polyphaotarsonemus latus), cyclamen dust mite
Dust mites such as (Steneotarsonemus pallidus), Tyrophagus putrescentiae, Robin mite
(Rhizoglyphus robini) and other mites, honey bee mites (Varroa jacobsoni) and other bees, mite ticks (Boophilus microplus), phytophthora ticks (Haemap
hysalis longicornis) and other ticks, sheep dwarf mite (Psoroptes ovis) and other dwarf mites, Sarcoptes scabiei and other crustaceans (Armadillidium vulgare), etc. Prunylenchus vulnus, potato cyst nematode (Globodera rostochiensis), soybean cyst nematode (Heterodera glycines), Meloidogyne hapla (Meloidogluenus aipus leucorrhea), Meloidogyne incognita , Spodoptera chinensis (Ponacea canaliculata), Slugs (Incilaria)
bilineata), Uskawamaimai (Acusta despecta sieb
Examples include mollusks such as oldiana) and Missjimaimai (Euhadra peliomphala).

Further, the compound of the present invention is effective in preventing adhesion of aquatic organisms at an extremely low concentration. Examples of the aquatic organisms include shellfish and algae such as blue mussels, barnacles, oysters, hydro worms, hydra, serpra, squirts, bryozoans, fucocilia, snails, aosa, aonouri, shionomidoro.

That is, the compounds of the present invention effectively control pests and plant diseases of orthoptera, hemiptera, lepidoptera, coleoptera, hymenoptera, diptera, termites and mites and lice at low concentrations. it can. Furthermore, the compound of the present invention can control adhesion of various aquatic organisms in seawater and freshwater to aquatic structures and the like.
On the other hand, the compounds of the present invention include extremely useful compounds that have almost no adverse effect on mammals, fish, crustaceans and beneficial insects.

The compound (1) of the present invention can be synthesized by the method described in Scheme 1. That is, the present compound (1)
Can be synthesized by reacting the compound (2), which can be synthesized according to the method described in WO97 / 40009, with the compound represented by the general formula (3). [Scheme 1]

[0167]

[Chemical 3]

[In the scheme 1, R, B, X and Y have the same meanings as described above, and L is a good leaving group such as chlorine atom, bromine atom, iodine atom, C ₁ -C ₄ alkylsulfonyloxy, Benzenesulfonyloxy, toluenesulfonyloxy, 1-imidazolyl, 1-pyrazolyl and the like. ].

In some cases, it may be preferable to use a base in the above method. As the base to be used, alkali metal alkoxides such as sodium ethoxide, sodium methoxide and potassium t-butoxide, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate. , Organic bases such as triethylamine, pyridine and DBU, organic lithium compounds such as butyllithium, lithium amides such as lithium diisopropropylamide and lithium bistrimethylsilylamide, and sodium hydride.

The above reaction can be carried out in a solvent inert to the reaction, and as the solvent, lower alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene, diethyl ether, tetrahydrofuran,
Ethers such as 1,4-dioxane, 1,2-dimethoxyethane and 1,2-diethoxyethane, acetone,
Ketones such as methyl ethyl ketone and methyl isobutyl ketone, halogenated hydrocarbons such as methylene chloride, chloroform and 1,2-dichloroethane, amides such as dimethylformamide, dimethylacetamide and 1,3-dimethylimidazolidinone, acetonitrile and the like. Examples thereof include nitriles, dimethyl sulfoxide, and mixed solvents thereof. In some cases, a mixed solvent of these solvents and water can be used, and good results may be obtained by adding a quaternary ammonium salt such as tetra-n-butylammonium bromide as a catalyst. The reaction temperature can be set to any temperature from -70 ° C to 200 ° C, and the range of 0 ° C to 150 ° C or, when a solvent is used, -70 ° C to the boiling point of the solvent is preferable. The base is 0.05 to 10 equivalents, preferably 0.
The range is from 05 to 3 equivalents.

The compound of the present invention can be obtained from the reaction solution by a conventional method, but if it is necessary to purify the compound of the present invention, it can be separated and purified by any purification method such as recrystallization or column chromatography. You can

Examples of compounds included in the present invention are shown in Table 1. The abbreviations in the table have the following meanings.

Me: methyl group, Et: ethyl group, Pr:
Propyl group, Bu: butyl group, Pen: Pentyl group, He
x: hexyl group, Hep: heptyl group, Oct: octyl group, Non: nonyl group, Dec: decyl group, Ph: phenyl group, n: normal, i: iso, s: secondary,
t: tertiary, c: cyclo.

[Table 1]

[0175]

[Chemical 4]

[0176]

[Chemical 5]

[0177]

[Chemical 6]

[0178]

[Chemical 7]

[0179]

[Table 1] ――――――――――――――――――――――――――――――――――― RB ―――――――――― ――――――――――――――――――――――――― H CH ₂ CH = CH ₂ H CH ₂ C ≡ CH H CSMe H CSPh H CS ₂ Me H CS ₂ Et H CS ₂ Ph H CSOMe H CSOEt H CSOPh H COCH ₂ C ≡ CH H COSMe H COSEt H COSCH ₂ Ph 2-F CS ₂ Me 2-F CS ₂ Et 2-F CS ₂ Ph 2-F CSOPh 2-F COSMe 2-F COSEt 3-F CS ₂ Me 3-F CS ₂ Et 3-F CS ₂ Ph 3-F CSOPh 3-F COSMe 3-F COSEt 4-F CS ₂ Me 4-F CS ₂ Et 4-F CS ₂ Ph 4-F CSOPh 4-F COSMe 4-F COSEt 4-Cl CS ₂ Et 4-Cl CSOPh 4-Cl COSMe 4-Cl COSEt 2-Br CS ₂ Me 2-Br CSOPh 2-Br COSMe 2-Br COSEt 3-Br CS ₂ Ph 3-Br CSOPh 3-Br COSMe 3-Br COSEt 4-Br CS ₂ Me 4-Br CS ₂ Et 4-Br CS ₂ Ph 4-Br CSOPh 4-Br COSMe 4-Br COSEt 4- I CS ₂ Me 4-I CS ₂ Et 4-I CS ₂ Ph 4-I CSOPh 4-I COSMe 4-I COSEt 2,4-F ₂ CS ₂ Me 2,4-F ₂ CS ₂ Et 2,4- F ₂ CS ₂ Ph 2,4-F ₂ CSOPh 2,4-F ₂ COSMe 2,4-F ₂ COSEt 2,6-F ₂ CS ₂ Me 2,6-F ₂ CS ₂ Et 2,6-F ₂ CS ₂ Ph 2,6-F ₂ CSOPh 2,6- F ₂ COSMe 2,6-F ₂ COSEt 3,4-F ₂ CS ₂ Me 3,4-F ₂ CS ₂ Et 3,4-F ₂ CS ₂ Ph 3,4-F ₂ CSOPh 3,4-F ₂ COSMe 3,4-F ₂ COSEt 2-Me COSMe 3-Me COSMe 4-Me CS ₂ Me 4-Me CS ₂ Et 4-Me CS ₂ Ph 4-Me CSOPh 4-Me COSMe 4-Me COSEt 4-Et CSOPh 4-Et COSMe 4-Et COSEt 4-nPr CSOPh 4-nPr COSMe 4-nPr COSEt 4-iPr CSOPh 4-iPr COSMe 4-iPr COSEt 4-nBu CSOPh 4-nBu COSMe 4-nBu COSEt 4-iBu CSOPh 4- iBu COSMe 4-iBu COSEt 4-sBu CSOPh 4-sBu COSMe 4-sBu COSEt 2-tBu COSMe 3-tBu COSMe 4-tBu CH ₂ CH = CH ₂ 4-tBu CH ₂ CH = CHCl 4-tBu CH ₂ C≡ CH 4-tBu CH ₂ C ≡ CCl 4-tBu CSMe 4-tBu CScPr 4-tBu CS (1-Me-cPr) 4-tBu CScHex 4-tBu CS (1-Me-cHex) 4-tBu CSCH = CH ₂ 4-tBu CSCH = CMe ₂ 4-tBu CSCH ₂ CH = CH ₂ 4-tBu CSCH ₂ C ≡ CH 4-tBu CSPh 4-tBu CS (2-Cl-Ph) 4-tBu CS (2-poly) 4- tBu CS (3-poly) 4-tBu CS (4-poly) 4-tBu CSCH ₂ Ph 4-tBu CS ₂ Me 4-tBu CS ₂ Et 4-tBu CS ₂ cPr 4-tBu CS ₂ (1-Me- cPr) 4-tBu CS ₂ cPen 4-tBu CS ₂ CH ₂ Ph 4-tBu CS ₂ CH ₂ CH = CH ₂ 4-tBu CS ₂ CH ₂ C ≡ CH 4-tBu CS ₂ Ph 4-tBu CSOMe 4-tBu CSOEt 4-tBu CS OcPr 4-tBu CSOcHex 4-tBu CSOPh 4-tBu CSO (4-F-Ph) 4-tBu CSO (4-Cl-Ph) 4-tBu CSO (4-Me-Ph) 4-tBu CSO (2-CF ₃ -Ph) 4-tBu CSO (2-MeO-Ph) 4-tBu CSO (2-CHF ₂ O-Ph) 4-tBu CSO (2-MeS-Ph) 4-tBu CSO (2-MeSO-Ph) 4-tBu CSO (2-MeSO ₂ Ph) 4-tBu CSO (2-CF ₃ S-Ph) 4-tBu CSO (2-CBrF ₂ SO-Ph) 4-tBu CSO (2-CHF ₂ SO ₂ -Ph ) 4-tBu CSO (3-NO ₂ -Ph) 4-tBu CSO (4-CN-Ph) 4-tBu CSO (4-NMe ₂ -Ph) 4-tBu CSO (2,6-F ₂ -Ph) 4-tBu CSO (2,4,6-Cl ₃ -Ph) 4-tBu CSO (3,4- (MeO) ₂ -Ph) 4-tBu CSO (3-tBu-Ph) 4-tBu CSO (2- 4-tBu CSOCH ₂ Ph 4-tBu CSOCH ₂ CH = CH ₂ 4-tBu CSOCH ₂ CMe = CH ₂ 4-tBu COC≡CH 4-tBu COCH ₂ C≡CH 4-tBu COSMe 4-tBu COSEt 4- tBu COS-nBu 4-tBu COS-iBu 4-tBu COScPr 4-tBu COScHex 4-tBu COSCH ₂ Ph 4-tBu COS (2-polysilver) 4-tBu COSCH = CH ₂ 4-tBu COSCH ₂ C≡CH 4- EtMe ₂ C CS ₂ Me 4-EtMe ₂ C CS ₂ Et 4-EtMe ₂ C CS ₂ Ph 4-EtMe ₂ C CSOPh 4-EtMe ₂ C COSMe 4-EtMe ₂ C COSEt 4-PhCH ₂ COSEt 4- (2-Cl-Ph) CH ₂ COSEt 4- (3-Cl-Ph) CH ₂ COSEt 4- (4-Cl-Ph) CH ₂ COSEt 4- (2-Me-Ph) CH ₂ COSEt 4 -(3,4-Cl ₂ -Ph) CH ₂ COSEt 4- (2,6-F ₂ -Ph) CH ₂ COSEt 4-CF ₃ COSEt 4- (CF ₃ ) ₂ CF COSEt 4-cPr COSMe 4- (1-Me-cPr) COSMe 4-cHex COSMe 4- (1-Me-cHex) COSMe 3-MeO COSMe 4-MeO COSMe 3,4- (MeO) ₂ COSMe 4-tBuO COSMe 3-Br-4-MeO COSMe 4-CH ₂ = CHCH ₂ O COSMe 4-CH ≡ CCH ₂ O COSMe 4-CHF ₂ O COSMe 4-CBrF ₂ O COSMe 4-CF ₃ O COSMe 4-CF ₃ CH ₂ O COSMe 4-MeS COSMe 4-iPrS COSMe 4-tBuS COSMe 4-MeSO COSMe 4-nBuSO ₂ COSMe 4-CH ₂ = CHCH ₂ S COSMe 4-CH ₂ = CHCH ₂ SO COSMe 4-CH ₂ = CHCH ₂ SO ₂ COSMe 4-CH≡CCH ₂ S COSMe 4-CH ≡ CCH ₂ SO COSMe 4-CH ≡ CCH ₂ SO ₂ COSMe 4-CHF ₂ S COSMe 4-CBrF ₂ S COSMe 4-CF ₃ S COSMe 4-CF ₃ CH ₂ S COSMe 4-CF ₃ SO COSMe 4-CF ₃ SO ₂ COSMe 4-CF ₂ = CHCH ₂ S COSMe 4-CF ₂ = CFCH ₂ SO COSMe 4-CF ₂ = CHCH ₂ SO ₂ COSMe 4-CN COSMe 4-NO ₂ COSMe 4-Me ₂ N COSMe 4- (1-Naphthyl) COSMe 4- (2-Naphthyl) COSMe 4-PhCH ₂ O COSEt 4-MeOC (O) COSMe 4-iPrOC (O) COSMe 4-tBuOC (O) COSMe 4-MeOCH ₂ COSMe 4-EtC (O) COSMe 4-CF ₃ C (O) COSMe 4-EtC (O) O COSMe 4-CF ₃ C (O) O COSMe 4-Me ₂ NC (O) O COSMe 4-Ph COSMe 4-PhO COSMe 4-PhC (O) COSMe 4- (Poly-2-yl) COSMe 4- (Poly-2-yl) O COSMe 4- (Thiophen-2-yl) COSMe 3-OCH ₂ O- Four COSMe 3-OCF ₂ O-4 COSMe 4-Me ₂ C = N COSMe 4-MePhC = N COSMe 3-CH ₂ CH ₂ CH ₂ -4 COSMe ―――――――――――――――――――――――――――――――――――

When the compound of the present invention is applied as an agricultural chemical, it is usually mixed with a suitable solid carrier or liquid carrier, and if desired, a surfactant, a penetrating agent, a spreading agent, a thickener, an antifreezing agent, a binder. , An anti-caking agent, a disintegrating agent, an anti-degrading agent, etc. are added to prepare a solution, emulsion, wettable powder, water solvent, granule wettable powder, granule water solvent, suspension agent, emulsion, suspoemulsion, It can be put to practical use as a preparation of any dosage form such as microemulsion, powder, granule and gel. Further, from the viewpoint of labor saving and improvement of safety, the formulation of any of the above dosage forms can be provided in a water-soluble package.

Examples of the solid carrier include natural mineral substances such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite and diatomaceous earth, calcium carbonate, ammonium sulfate, sodium sulfate and potassium chloride. Inorganic salts such as, synthetic silicic acid and synthetic silicates.

Examples of the liquid carrier include alcohols such as ethylene glycol, propylene glycol and isopropanol, aromatic hydrocarbons such as xylene, alkylbenzene and alkylnaphthalene, ethers such as butyl cellosolve, ketones such as cyclohexanone, and the like.
Examples thereof include esters such as γ-butyrolactone, acid amides such as N-methylpyrrolidone and N-octylpyrrolidone, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil, and water.

These solid and liquid carriers may be used alone or in combination of two or more kinds.

Examples of the surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid ester, sorbitan fatty acid ester and polyoxyethylene fatty acid ester. Nonionic surfactants such as oxyethylene sorbitan fatty acid ester, alkyl sulfates, alkylbenzene sulfonates,
Lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonate, alkyl naphthalene sulfonate, salt of formalin condensate of naphthalene sulfonic acid, salt of formalin condensate of alkyl naphthalene sulfonic acid,
Anionic surfactants such as polyoxyethylene alkylaryl ether sulfates and phosphates, polyoxyethylene styrylphenyl ether sulfates and phosphates, polycarboxylates and polystyrenesulfonates, alkylamine salts and alkyl quaternary ammonium salts Examples include cationic surfactants and amphoteric surfactants such as amino acid type and betaine type surfactants.

The content of these surfactants is not particularly limited, but is preferably in the range of 0.05 to 20 parts by weight per 100 parts by weight of the preparation of the present invention. Further, these surfactants may be used alone or in combination of two or more kinds.

When the compound of the present invention is used as a pesticide, other herbicides of various species, various insecticides, acaricides, nematicides, fungicides, plant growth regulators may be used as necessary during formulation or spraying. It may be mixed and applied with an agent, a synergist, a fertilizer, a soil conditioner and the like.

[0187] In particular, when mixed with other pesticides or plant hormones, application can be expected to reduce costs by reducing the amount of application, to expand the insecticidal spectrum due to the synergistic action of the mixed agents, and to have a higher pest control effect. On this occasion,
It is also possible to combine a plurality of known pesticides at the same time. The types of pesticides used in combination with the compound of the present invention include, for example, Farm Chemicals Handbook (Farm).
Chemicals Handbook, 1999 edition. Specific examples of the common names are as follows, but the general names are not limited thereto.

Bactericide: Acibenzolar-S-methyl (ac
ibenzolar-S-methyl), acylaminobenzamide (acyla
minobenzamide, ambam, ampropyfos, anilazine, azaconazole, azoxystrobin
robin), benalaxyl, benodanil (be
nodanil), benomyl, benazole (ben
thiazole), benzamacril, binapacryl, biphenyl, bitertanol, bethoxazin
e), bordeaux mixture, blasticidin-S, bromoconazole
onazole), bupirimate, buthiobate, calcium polysulfide (calciu)
m polysulfide), captafol, captan, copper oxychloride
oxychloride), carpropamid (carpropamid), carbendazine (carbendazim), carboxin (carboxi)
n), CGA-279202, quinomethionate (chinomethio
nat), chlobenthiazone, chlorfenazol, chloroneb
b), chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazole
zol), cyprodinil, cyproflam (c
yprofuram), dazomet, debacarb
carb), dichlorophen (dichlorophen), diclobutrazol (diclobutrazol), diclofuranide (diclhlo)
fluanid), diclomedine, dichloran, diethofencar
b), diclocymet, difenoconazole, diflumetor
im), dimethirimol, dimethomorph, diiconazole,
Diniconazole-M, dinocap (d
inocap), diphenylamine (diphenylamine), dipyrithione (dipyrithione), ditalimfos (ditalimfo)
s), dithianon, dodemorph
h), dodine, drazoxolo
n), edifenphos, epoxiconazole, etaconazol
e), ethirimol, etridianol (et
ridiazole), famoxadone, fenarimol, febuconazol
e), fenamidone, fendazoslum
(fendazosulam), fenfuram, fenhexamid, fenpiclonil (fenpiclo)
nil), fenpropidin, fenpropimorph, fentin,
Felvan, ferimzone,
Fluazinam, fludioxonil (fludi
oxonil), fluoroimide, fluquinconazole, flusilazole (flu)
silazole), flusulfamide (flusulfamide), flutolanil (flutolanil), flutriafol (flutri)
afol), folpet, fosetyl-aluminium, fuberidazole (fuber)
idazole), furalaxyl, flametopyr
(furametpyr) guazatine, hexachlorobenzene, hexaconazole (h
exaconazole), hymexazol, imazalil, imibenconazo
le), iminoctadine, ipconazole, iprobenfos, iprodione, isoprothiolane
hiolane), iprovalicarb, kasugamycin, kresoxime-methyl (k
resoxim-methyl), mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metconazol
e), metasulfocarb, methylam (m
etiram), metominostrobin,
Microbutanil (myclobutanil), MTF-753, nabam, nickel bis (dimethyldithiocarbamate), nitrothal-isopropyl (nitrothal-isopropyl),
Nuarimol, NNF-9425, octhilinone, ofurace, oxadixyl, oxycarboxin
n), oxpoconazole fumarate
marate), pefurzoate (pefurzoate), penconazole (penconazole), penciclone (pencycuron),
Phthalide, piperalin,
Polyoxins, potassium hydrogen carbonate (potass
ium hydrogen carbonate), probenazole (probenazo
le), prochloraz, procymidone (pr)
ocymidone), propamocarb hyd (propamocarb hyd
rochloride), propiconazole (propiconazole),
Propineb, pyrazophos,
Pyrifenox, pyrimethanil (pyrim)
ethanil), pyroquilon, quinomethionate, quinoxyphen
n), quintozene, RH7281, sodium hydrogen carbonate, sodium hypochlorite, sulfur,
Spiroxamine, tebuconazole (teb
uconazole), technazene, tetraconazole, thiabenda
zole), thiadiazin / milneb, thifluzamide, thiophanate-methyl
phanate-methyl), thiram, tolclofos-
Methyl (tolclofos-methyl), Tolylfuranide (tolylf)
luanid), triadimefon, triadimenol, triazoxid
de), tricyclazole, tridemorph, triflumizol
e), triforine, trithiconazole (tr
iticonazole), validamycin, vinclozolin, zinc sulfat
e), zineb, ziram, and shiitake mycelium extract.

Bactericidal agent: Streptomycin (st
reptomycin), tecloftalam, oxyterracycline and oxolinic acid.

Nematicides: aldoxycarb
b), kazusaphos, fostiazate (fo)
sthiazate), fosthietan, oxamyl and fenamiphos.

Acaricide: acequinocy
l), amitraz, bifenaset (bifena)
zate), bromopropylate, chinomethionat, chlorobezilate, clofentezin
e), cyhexatine, dicofol (d
icofol), dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropatrin, fenproximate, fenproximate, halfenprox
x), hexythiazox, milbemectin, propargit
e), pyridaben, pyrimidifen (pyri)
midifen) and tebufenpyrad.

Insecticide: abamectin, acephate, acetamipir
id), aldicarb (aldicarb), allethrin (alle)
thrin), azinphos-methyl, bendiocarb, benfurcarb
acarb), bensultap, bifenthrin, buprofezin, butocarboxin, carbaryl
yl), carbofuran (carbofuran), carbosulfan (carbosulfan), cartap (cartap), chlorfenapyr (chlorfenapyr), chlorpyrif (chlorpyrif)
os), chlorfenvinphos, chlorfluazuron, chlorfluazuron, clothianidin, chromafenozid
e), chlorpyrifos-methyl,
Cycloprothrin, cyfluthrin (c
yfluthrin), beta-cyfluthrin
n), cypermethrin, cyromazine (c
yromazine), cyhalothrin, lambda
Cyhalothrin (lambda-cyhalothrin), deltamethrin (deltamethrin), diafenthiuro (diafenthiuro)
n), diazinon, diacroden
oden), diflubenzuron, dimethylvinphos, diophenolane (dio)
fenolan), disulfoton (disulfoton), dimethoate (dimethoate), dinotefuran (dinotefuran),
Emamectin-benzoate, EP
N, esfenvalerate, ethiofencarb, ethiprol
e), etofenprox, etrimfos, fenitrothione
n), fenobucarb, fenoxycarb, fenpropathri
n), fenvalerate, fipronil, fluacrypyrim, flucytrinate, flufenoxuron, flufenoxuron, flufenprox
prox), tau-fluvalinate,
Fonophos, formetanat
e), formothion, formothion, furathiocarb, halofenozide,
Hexaflumuron, hydramethylnon, imidacloprid
d), isofenphos, indoxacarb, isoprocarb, isoxathion, lufenuron
ron), malathion (malathion), metal dehydration (meta)
ldehyde), methamidophos, methidathion, methacrifo
s), metalcarb, methomyle
l), mesoprene, methoxychlor (m
ethoxychlor), methoxyphenozid
e), monocrotophos, muscalure, nitenpyram, omethoate, oxydemeton-methyl (oxyde)
meton-methyl), oxamyl, parathion, parathion-methy
l), permethrin, fentoate (p
henthoate), oxime (phoxim), phorate (phora)
te), phosalone, phosme
t), phosphamidon, pirimicarb, pirimiphos-met
hyl), profenofos, protrifenbute, pymetrozin
e), pyraclofos, pyriproxyfen, rotenone, sulprofos, silafluofe
n), spinosad, sulfotep
p), tebufenozide, teflubenzuron, tefluthorin,
Terbufos, tetrachlorobinphos (tetr
achlorvinphos), thiacloprid, thiocyclam, thiodicar
b), thiamethoxam, thiofanox, thiometon, tolfenpyrad, tralomesulin
thrin), trichlorfon, triazuron, triflumuron and vamidothion.

The application dose of the compound of the present invention varies depending on the application scene, application time, application method, cultivated crop, etc., but is generally 0.00 per hectare (ha) as the active ingredient amount.
About 5 to 50 kg is suitable.

Next, formulation examples of preparations using the compound of the present invention will be shown. However, the compounding examples of the present invention are not limited to these. In the following formulation examples, "part" means part by weight.

[Wettable powder] Compound of the present invention 0.1 to 80 parts Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts As other materials, for example, anticaking agents, decomposition inhibitors, etc. I can give you.

[Emulsion] Compound of the present invention 0.1 to 30 parts Liquid carrier 45 to 95 parts Surfactant 4.9 to 15 parts Others 0 to 10 parts Examples of other materials include spreading agents and decomposition inhibitors. To be

[Suspension] Compound of the present invention 0.1 to 70 parts Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts As other, for example, antifreezing agent, thickener Etc.

[Granule wettable powder] Compound of the present invention 0.1 to 90 parts Solid carrier 0 to 98.9 parts Surfactant 1 to 20 parts Others 0 to 10 parts As other materials, for example, a binder, a decomposition inhibitor, etc. Can be mentioned.

[Liquid] Compound of the present invention 0.01 to 70 parts Liquid carrier 20 to 99.99 parts Others 0 to 10 parts Examples of other include, for example, antifreezing agents, spreading agents and the like.

[Granule] Compound of the present invention 0.01 to 80 parts Solid carrier 10 to 99.99 parts Others 0 to 10 parts Examples of other include a binder and a decomposition inhibitor.

[Powder] Compound of the present invention 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0 to 5 parts Other examples include drift inhibitors and decomposition inhibitors.

[Formulation Examples] Next, specific formulation examples of agricultural chemicals containing the compound of the present invention as an active ingredient will be shown, but the present invention is not limited thereto.

In the following formulation examples, "part" means part by weight.

[Formulation Example 1] Wettable powder of the present invention Compound No. 1 20 parts Pyrophyllite 76 parts Sorpol 5039 2 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) Carplex # 80D 2 parts (synthetic hydrous silicic acid: Shiono Gyosei Co., Ltd. trade name) The above is uniformly mixed and ground to obtain a wettable powder.

[Formulation Example 2] Emulsion Compound No. of the present invention 1 5 parts xylene 75 parts N-methylpyrrolidone 15 parts Sorpol 2680 5 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) And

[0206] [Formulation Example 3] Suspension agent (flowable agent) Inventive Compound No. 25 copies Agrisol S-710 10 parts (Nonionic surfactant: Kao Corporation trade name) Lunox 1000C 0.5 part (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) Xanthan gum 0.2 parts Water 64.3 parts After uniformly mixing the above, wet pulverization is performed to obtain a suspension agent.

[Formulation Example 4] Granule wettable powder (dry flowable agent) 1 75 parts Hitenol NE-15 5 parts (anionic surfactant: Dai-ichi Kogyo Seiyaku Co., Ltd. trade name) Vanilex N 10 parts (anionic surfactant: Nippon Paper Industries Co., Ltd. trade name) Carplex # 80D 10 parts (synthetic hydrous silicic acid: trade name of Shionogi Seiyaku Co., Ltd.) After uniformly mixing and pulverizing the above, a small amount of water was added, and the mixture was stirred and mixed, granulated by an extrusion granulator, dried, and granulated water. Use as a Japanese medicine.

[Formulation Example 5] Granules Compound of the present invention No. 15 parts bentonite 50 parts talc 45 parts After uniformly mixing and pulverizing the above, a small amount of water is added and mixed by stirring, granulated by an extrusion granulator, and dried to obtain granules.

[Formulation Example 6] Powder Inventive Compound No. 1 part 3 Carplex # 80D 0.5 copy (Synthetic hydrous silicic acid: trade name of Shionogi Pharmaceutical Co., Ltd.) Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above is uniformly mixed and pulverized to obtain a powder.

In use, the wettable powder, emulsion, flowable powder and granular wettable powder are diluted 50 to 20000 times with water to prepare an active ingredient in an amount of 0.005 to 1 hectare (ha).
Sprinkle so that it weighs 50 kg.

When the compound of the present invention is applied as an aquatic organism adhesion preventive agent, it is formulated into an appropriate dosage form such as a paint, solution, emulsion, pellet or flake to give aquatic organism adhesion preventive agent to a wide range of objects. It can be used by appropriately selecting a commonly used method such as coating, spraying, impregnation, addition in water, and installation in water according to the place of use, purpose and dosage form. For the preparation of these paints, solutions, emulsions, etc., a commonly practiced formulation can be adopted. Furthermore, for example, the compound of the present invention is incorporated at the stage of manufacturing a rope or a fiber material used for fishing nets, etc., and the rope or the fiber material itself is used in a dosage form and a method other than the above, such as imparting aquatic organism adhesion control performance to the rope or the fiber material itself. You can also The aquatic organism adhesion preventing agent of the present invention may be used alone, or may be used as a mixture with an aquatic organism adhesion preventing agent other than the present invention.

When the agent for preventing the attachment of aquatic organisms of the present invention is used in the form of an antifouling paint, for example, the compound of the present invention is blended with a film forming agent to prepare a paint for use. As the film forming agent, oil varnish, synthetic resin, artificial rubber or the like is used. Further, a solvent, a pigment or the like may be used if necessary. When a paint is prepared, the compound of the present invention has no upper limit in concentration as long as a coating film can be formed, but 1 to 50% by weight, preferably 5 to 5% by weight based on the weight of the antifouling paint.
It is mixed in a ratio of 20% by weight.

When the aquatic organism adhesion preventing agent of the present invention is used in the form of a solution, for example, a solution in which the compound of the present invention is dissolved in a solvent together with a film forming agent is prepared and used. As the coating film forming agent, synthetic resin, artificial rubber, natural resin or the like is used, and as the solvent, xylene, toluene, cumene, methyl ethyl ketone, methyl isobutyl ketone, acetone or the like is used. Further, additives such as a plasticizer may be used if necessary. When a solution is prepared, the compound of the present invention has no upper limit to the concentration as long as the solution can be formed, but is compounded at a ratio of 1 to 50% by weight, preferably 5 to 30% by weight based on the weight of the solution. .

When the aquatic organism adhesion preventing agent of the present invention is used in the form of an emulsion, a surfactant is added to the compound of the present invention to prepare a desired emulsion according to a general method for preparing an emulsion. There is no particular limitation on the type of surfactant used. When the emulsion is prepared, the compound of the present invention has no upper limit to the concentration as long as the emulsion can be formed, but is compounded at a ratio of 1 to 50% by weight, preferably 5 to 30% by weight based on the weight of the emulsion. .

When the aquatic organism adhesion preventing agent of the present invention is used in the form of pellets or flakes, the compound of the present invention and, if necessary, a hydrophilic resin such as polyethylene glycol which is solid at room temperature are used as a base. A plasticizer, a surfactant and the like may be blended as constituent components and formed into pellets or flakes by a method such as melt molding or compression molding, which can be used. In the case of preparing pellets or flakes, the compound of the present invention has no upper limit to the concentration as long as pellets or flakes can be formed, but 20 to 95% by weight, preferably 30 to 9% by weight based on the weight of the pellets or flakes.
It is blended in a proportion of 0% by weight.

[0216]

EXAMPLES The synthesis examples and test examples of the compound of the present invention will be specifically described below as Examples, but the present invention is not limited thereto.

[Synthesis Example 1] 2- (4- (tert-butyl) phenyl) -2-cyano-1- (1,3,4-trimethylpyrazol-5-yl) vinyl ethylthioformate [2- ( 4- (tert-butyl) phenyl) -2-cyano-1- (1,3,
4-trimethylpyrazol-5-yl) vinyl ethylthioformate)
Synthesis of (Compound No. 1, 2) 2- (4- (tert-butyl) phenyl) -3-hydroxy-3- (1,3,4-trimethylpyrazole-
5-yl) prop-2-enenitrile (0.50 g) and triethylamine (0.20 g) in tetrahydrofuran (15 ml)
It was dissolved in, and 0.22 g of ethylchlorothiol formate was added at 0 ° C. After stirring at room temperature for 3 hours, the reaction solution was added to water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 9: 1) to obtain the desired product E
Form (Compound No. 1) 0.27 g and Z form (Compound No. 1).
2) 0.36 g was obtained.

¹ H-NMR (CDCl ₃ , δppm) E form: 1.25 (3H, t), 1.35 (9H, s), 2.10 (3H, s), 2.21 (3H, s),
2.84 (2H, q), 3.87 (3H, s), 7.49 (2H, d), 7.58 (2H, d) Z body: 1.27 (9H, s), 1.34 (3H, t), 1.86 (3H, s) , 2.16 (3H, s),
2.90 (2H, q), 3.41 (3H, s), 7.06 (2H, d), 7.29 (2H, d)

Synthesis Example 2 2- (4- (tert-butyl) phenyl) -3- (phenoxythioxomethoxy) -3- (1,3,4-trimethylpyrazole-5-
Il) prop-2-enenitrile [2- (4- (tert-butyl) p
henyl) -3- (phenoxythioxomethoxy) -3- (1,3,4-trimethyl
pyrazol-5-yl) prop-2-enenitrile] (Compound No. 3,
Synthesis of 4) In the same manner as above except that phenylchlorothionoformate was used as a raw material, the target E-form (Compound No. 3)
0.26 g and 0.43 g of Z form (Compound No. 4) were obtained.

¹ H-NMR (CDCl ₃ , δppm) E form: 1.37 (9H, s), 2.16 (3H, s), 2.23 (3H, s), 3.97 (3H, s),
6.94 (2H, d), 7.1-7.5 (3H, m), 7.52 (2H, d), 7.68 (2H, d) Z body: 1.29 (9H, s), 1.96 (3H, s), 2.19 (3H, s), 3.38 (3H, s),
7.12 (4H, d), 7.3-7.5 (5H, m)

[Test Example] Next, the usefulness of the compound of the present invention as an agricultural chemical will be specifically described in the following test examples.

[Test Example 1] Acaricidal efficacy test against Nite spider mite Leaf of kidney bean was cut into a circle with a diameter of 3.0 cm using a leaf punch and placed on a damp filter paper on a styrene cup having a diameter of 7 cm. Add 1 larvae of the spider mite to each leaf
0 animals were inoculated. 5% of the compound of the invention described in the description
An emulsion (25% wettable powder depending on the compound was tested) was diluted with water containing a spreading agent to prepare a chemical solution having a concentration of 500 ppm, and this chemical solution was used in an amount of 2 ml per styrene cup using a rotary spraying tower. Scatter and store in a constant temperature room at 25 ° C for 6
The number of dead insects after the lapse of days was investigated, and the death rate was calculated from the following formula. The test was conducted in a two-district system. Mortality rate (%) = {Number of dead insects / (Number of dead insects + Number of surviving insects)} × 1
As a result, the following compounds showed 100% mortality. Inventive compound No .: 1, 2, 3, 4

[0223]

INDUSTRIAL APPLICABILITY The present invention provides novel pesticides, particularly insecticides and acaricides, and also provides an aquatic organism adhesion preventive agent which has little influence on the ecosystem and secondary pollution.

   ─────────────────────────────────────────────────── ─── Continued front page    (72) Inventor Toshinori Ito             1470 Shiraoka, Shiraoka-cho, Minami-Saitama-gun, Saitama Nissan             Chemical Industry Co., Ltd. F-term (reference) 4H011 AC04 AD01 BA01 BB09 BC01                       BC07 BC09 BC17 BC18 BC19                       BC20 DA02 DA15 DA16 DC04                       DC06 DC08 DH03 DH14

Claims (6)

[Claims] 1. Formula (1): [Chemical 1] [Wherein, X and Y are each independently H, halogen, C₁
~ C_FourAlkyl or C₁~ C_FourIs a haloalkyl, B is C₂~ C₆Alkenyl, C₂~ C₆Haloalkenyl,
C₂~ C₆Alkynyl, C₂~ C₆Haloalkynyl, C
(O) Rf or C (S) Rg, R is H, halogen, C₁~ C₆Alkyl, substituted with Rb
C₁~ C_FourAlkyl, C₁~ C_FourHaloalkyl, C₁~
C_FourC optionally substituted with alkyl₃~ C₇Cycloa
Rukiru, C₁~ C_FourC optionally substituted with alkyl₃
~ C₇Halocycloalkyl, C₁~ C₆Alkoxy, C₂~
C_FourAlkenyloxy, C₂~ C_FourHalo alkenyl oki
Shi, C₂~ C_FourAlkynyloxy, C₁~ C_FourHalo arcoki
Shi, C₁~ C_FourAlkylsulfenyl, C₁~ C_FourAlkyl
Sulfinyl, C₁~ C_FourAlkylsulfonyl, C₂~ C_Four
Alkenylsulfenyl, C₂~ C_FourAlkenyl sulfi
Nil, C ₂~ C_FourAlkenylsulfonyl, C₂~ C_FourArchi
Nilsulphenyl, C₂~ C_FourAlkynylsulfinyl,
C₂~ C_FourAlkynylsulfonyl, C₁~ C_FourHaloalkyl
Sulfenyl, C₁~ C_FourHaloalkylsulfinyl, C
₁~ C_FourHaloalkylsulfonyl, C₂~ C_FourHalo archeni
Rusulfenyl, C₂~ C_FourHaloalkenylsulfini
Le, C₂~ C_FourHaloalkenylsulfonyl, CN, N
O₂, -NU¹U², Naphthyl, Rb substituted methoki
Shi, C₂~ C_FiveAlkoxycarbonyl, C₂~ C_FourArcoki
Cyalkyl, C₂~ C_FourAlkylcarbonyl, C₂~ C_FourHa
Roalkylcarbonyl, C₂~ C_FiveAlkylcarbonyl
Kish, C₂~ C_FiveHaloalkylcarbonyloxy, C₃~
C₇Dialkylaminocarbonyloxy, substituted with Z
Optionally substituted phenyl, optionally substituted with Z
Noxy, benzoyl optionally substituted with Z, and Z
Optionally substituted pyridyl, optionally substituted with Z
Pyridyloxy, thieny optionally substituted with Z
Group, methylenedioxy bonded at adjacent substitution positions, next to
Halomethylenedioxy and-bonded at adjacent substitution positions
N = CT²T³1 to 4 substitutions selected from
A group or an alkylene group bonded at adjacent substitution positions
A 5- to 8-membered ring formed by Z is independently halogen, C₁~ C_FourAlkyl, C
₁~ C_FourHaloalkyl, C₁~ C_FourAlkoxy, C₁~ C_FourHa
Lowalkoxy, C₁~ C_FourAlkylsulfenyl, C₁~
C_FourAlkylsulfinyl, C₁~ C_FourAlkyl sulfoni
Le, C₁~ C_FourHaloalkylsulfenyl, C₁~ C_FourHalo
Alkylsulfinyl, C₁~ C_FourHaloalkylsulfoni
Le, NO₂, CN, -NU¹U²And C₂~ C_FiveAlkoxyca
1 to 5 substituents arbitrarily selected from rubonyl
And Rb is halogen, C₁~ C_FourAlkyl and C₁~ C_FourA
Substituted with one or more substituents selected from Lucoxy
It may be phenyl, Rf is C₂~ C₆Alkynyl or SRh, Rg is C₁~ C₆Alkyl, C₂~ C₆Alkenyl, C₂~
C₆Alkynyl, C₁~ C₆Alkoxy, C₂~ C₆Arche
Nyloxy, C₂~ C₆Alkynyloxy, C₁~ C₆Al
Kirsulphenyl, C₂~ C₆Alkenylsulfenyl,
C₂~ C₆Alkynylsulfenyl, C₁~ C_FourIn alkyl
C which may be substituted₃~ C₇Cycloalkyl, C₁~
C_FourC optionally substituted with alkyl₃~ C₇Cycloa
Lucyloxy, C₁~ C_FourMay be substituted with alkyl
I C₃~ C₇Cycloalkylsulfenyl, substituted with Z
Optionally substituted phenyl, optionally substituted with Z
Phenylsulfenyl optionally substituted with Noxy, Z
R, benzyl optionally substituted with Z, substituted with Z
Optionally substituted benzyloxy, optionally substituted with Z
Benzylsulfenyl, pyridyl, pyridyloxy,
Pyridylsulfenyl, pyrazolyl, pyrazolyloxy
Or pyrazolyl sulphenyl, Rh is C₁~ C₆Alkyl, C₂~ C₆Alkenyl, C₂~
C₆Alkynyl, C₁~ C_FourEven if it is substituted with alkyl
Good C₃~ C₇Cycloalkyl, may be substituted with Z
Benzyl, pyridyl or pyrazolyl, T²And T³Are each independently H, phenyl or benzyl.
Or C₁~ C₆Alkyl or T²And T³And
Form a 5- to 8-membered ring with the carbon atoms attached
Well, U¹And U²Are each independently H, C₁~ C₆Alkyl, C
₂~ C_FourAlkylcarbonyl, phenyl or benzyl
Represents or U¹And U²And the carbon atom that is bonded to
Together, they may form a 5- to 8-membered ring. ] Represented by
Acrylonitrile compound. 2. R may be substituted with H, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₄ alkyl substituted with Rb, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkyl Good C
₃ -C ₇ cycloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₄
Haloalkoxy, methoxy substituted with ^{-NU 1 U 2, Rb, C} 2 ~C 5 alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, C ₂ -C ₄ alkylcarbonyl, C ₂ -C ₄ haloalkylcarbonyl, C ₂ To C ₅ alkylcarbonyloxy, C _{2 to} C ₅ haloalkylcarbonyloxy and 1 to 4 substituents selected from phenyl optionally substituted with Z, B is C (O) Rf or C (S) is Rg, Rf is SRh, Rg is C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ ~
C ₆ alkynyl, C ₁ -C ₆ alkoxy, C ₂ -C ₆ alkenyloxy, C ₂ -C ₆ alkynyloxy, C ₁ -C ₆ alkylsulfenyl, C ₂ -C ₆ alkenylsulfenyl,
C ₂ -C ₆ alkyl Nils Le phenyl, C ₁ -C ₄ optionally substituted by alkyl C ₃ -C ₇ cycloalkyl, C ₁ ~
C ₄ may be substituted by alkyl C ₃ -C ₇ cycloalkyloxy, C ₁ -C ₄ alkyl optionally substituted with C ₃ -C ₇ cycloalkyl sulfenyl may be substituted with Z Phenyl, phenoxy optionally substituted with Z, phenylsulphenyl optionally substituted with Z, benzyl optionally substituted with Z, benzyloxy optionally substituted with Z or optionally substituted with Z. Optionally benzylsulfenyl, Rh is C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C _2-
The acrylonitrile compound according to claim 1, which is C ₆ alkynyl, C ₃ -C ₇ cycloalkyl optionally substituted with C ₁ -C ₄ alkyl or benzyl optionally substituted with Z. Wherein R is, H, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ optionally substituted by alkyl C ₃ -C ₇ cycloalkyl, C ₁ ~ ₁ to ₄ substituents selected from C ₆ alkoxy, C _{1 to} C ₄ haloalkoxy and phenyl optionally substituted with Z, and Rg is C _{1 to} C ₆ alkyl, C _{1 to} C ₆ alkoxy, C ₁ ~
C ₆ alkylsulfenyl, phenyl optionally substituted with Z, phenoxy optionally substituted with Z or phenylsulfenyl optionally substituted with Z, Rh is C ₁ -C ₆ alkyl The acrylonitrile compound according to claim 2. 4. R is 1 to 4 substituents selected from halogen, C ₁ -C ₆ alkyl and C ₁ -C ₄ haloalkyl, Rg is phenoxy, Rh is methyl or The acrylonitrile compound according to claim 3, which is ethyl. 5. An agrochemical comprising one or more of the acrylonitrile compounds according to claims 1 to 4 as an active ingredient. 6. An aquatic organism adhesion preventing agent comprising one or more of the acrylonitrile compounds according to claims 1 to 4 as an active ingredient.