JPH11269173A - Acrylonitrile compound and pesticide - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an acrylonitrile compound high in safety, manifesting an excellent pesticide activity, useful for insecticides in agriculture and horticulture, stock raising and hygienic fields, and acaricide, nematicide or the like. SOLUTION: This compound is expressed by the formula [Q is a (substituted) thiazolyl or a pyrazolyl; A is a (substituted)phenyl, a (substituted)naphthyl or a (substituted) heterocycle(heterocycle is thienyl, furyl, pyrrole or the like); B is H, a 1 to 4C alkyl, a 1 to 4C haloalkyl or the like], for example, 3-(4- choloro-1,3-dimethylpyrazol-5-yl)-3-hydroxy-2-(2-pyrazynilthiazol-4-yl )-acrylonitrile. The compound of the formula is obtained by reacting an acetonitrile derivative with an acid chloride or an ester or an acid anhydride, and then, reacting the product with an alkyl halide or an alkylphosphonate. The reaction is preferably carried out using a base (for example; sodium ethoxide, sodium hydroxide or the like) in a solvent (methanol, benzene or the like).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a novel acrylonitrile compound and an agrochemical containing the compound as an active ingredient. The pesticides in the present invention include insecticides, acaricides, nematicides, herbicides, fungicides, and the like, and particularly insecticides, acaricides, and nematicides in the fields of agriculture, horticulture, livestock, and sanitation. .

[0002]

2. Description of the Related Art An acrylonitrile derivative is disclosed as a pesticide in JP-A-53-92769, and as an agricultural chemical in International Patent Application Publication (WO97 / 40009). JP-A-60-11452 discloses 2- (4-chlorophenyl) -3 as a herbicide.
-(3-Pyridinyl) -3-oxopropionitrile is described, and JP-A-60-11401 describes the compound as a bactericide.

[0003]

With the long-term use of insecticides and fungicides, pests have recently acquired resistance,
Control with conventional insecticides and fungicides has become difficult.
Some insecticides are highly toxic, and some are persisting in ecosystems due to persistence. Therefore, the development of new insecticides and fungicides with low toxicity and low residue is always expected.

[0004]

Means for Solving the Problems In order to solve the above problems, the present inventors have demonstrated excellent pest control activity at a low dose and against non-target organisms such as mammals, fish and beneficial insects. As a result of continuing research to develop a pesticide having almost no adverse effects, the present inventors have found that the following compounds have high safety and excellent pesticidal activity and completed the present invention. That is, the present invention is a compound described in the following [1] to [5] (hereinafter referred to as the present compound) and an agricultural chemical containing the compound as an active ingredient.

[1] Equation (1):

[0006]

Embedded image

[Wherein Q is R and (R¹) Replace with n
Thiazolyl group, or R and (R¹) Replace with n
A pyrazolyl group wherein A is substituted with W
Phenyl, naphthyl optionally substituted with W,
Or a heterocyclic group optionally substituted by Y (however,
Elementary ring groups are thienyl, furyl, pyrrolyl, oxazolyl
, Isoxazolyl, thiazolyl, isothiazolyl,
Lazolyl, imidazolyl, 1,3,4-oxadiazoli
1,2,4-oxadiazolyl, 1,3,4-thia
Diazolyl, 1,2,4-thiadiazolyl, 1,2,4
-Triazolyl, 1,2,3-thiadiazolyl, 1,
2,3-triazolyl, 1,2,3,4-tetrazoli
, Pyridinyl, pyrimidinyl, pyrazinyl, pyridazi
Nil, 1,3,5-triazinyl, 1,2,4-tria
Zinyl, indazolyl, benzoxazolyl, quinolini
, Isoquinolinyl, quinoxalinyl, phthalazinyl,
Cinolinyl or quinazolinyl. ) And B
Is H, C₁~ C_FourAlkyl, C₁~ C_FourHaloalkyl, C
_Two~ C_FourAlkoxyalkyl, CH_ThreeSCH_Two, CH_ThreeOC_Two
H_FourOCH_Two, R^aC substituted with₁~ C_FourAlkyl, R^bso
Replaced C₁~ C_FourAlkyl, tetrahydropyranyl,
(CH_Three)_ThreeSi, C₁~ C_FourAlkylsulfonyl, halogen
Or C₁~ C_FourAlkyl which may be substituted with alkyl
Phenylsulfonyl, -SO_TwoCF_Three, C₁~ C_FourMono-archi
Luminosulfonyl, C_Two~ C₈Dialkylamino sulfo
Nil, phenylaminosulfonyl, C_Two~ C_FiveMono-archi
Ruaminothiocarbonyl, C_Three~ C₉Dialkylaminothi
Ocarbonyl, C_Two~ C_FiveCyanoalkyl, C_Three~ C₉Al
Coxycarbonylalkyl, -C (= O) T¹, -P
(= O) T^TwoT^Three, -P (= S) T^TwoT^Three, Alkali metal source
Element, alkaline earth metal atom or NHT^FourT^FiveT⁶In
R represents a heterocyclic group optionally substituted with G (provided that R is
This heterocyclic group is furyl, pyrrolyl, oxazolyl, iso-
Xazolyl, thiazolyl, isothiazolyl, pyrazoly
, Imidazolyl, 1,3,4-oxadiazolyl,
1,2,4-oxadiazolyl, 1,3,4-thiadia
Zolyl, 1,2,4-thiadiazolyl, 1,2,4-to
Liazolyl, 1,2,3-thiadiazolyl, 1,2,3
-Triazolyl, 1,2,3,4-tetrazolyl, pyri
Midinyl, pyrazinyl, pyridazinyl, 1,3,5-to
Riadinyl, 1,2,4-triazinyl, benzothiazo
Ril, benzimidazolyl, indazolyl, benzooxy
Sazolyl, quinolinyl, isoquinolinyl, quinoxalini
, Phthalazinyl, cinnolinyl or quinazolinyl
is there. ) And R¹Is halogen, C₁~ C_FiveAlkoki
Cicarbonyl, NO_Two, CN, -NU¹U^TwoOr -N =
CT⁷T⁸And n is an integer of 0 or 1;
Is halogen, C₁~ C_TenAlkyl, R^aC substituted with
₁~ C_FourAlkyl, C _Two~ C₆Alkenyl, C_Two~ C₆Al
Quinyl, C₁~ C₆Haloalkyl, C_Two~ C₆Haloalkene
Le, C_Two~ C₆Haloalkynyl, C_Three~ C₆Halocycloal
Kill, C₁~ C_ThreeC optionally substituted with alkyl_Three~
C₆Cycloalkyl, C₁~ C₆Alkoxy, C_Two~ C₆A
Lucenyloxy, C_Two~ C₆Alkynyloxy, C₁~ C_Four
Haloalkoxy, C_Two~ C₆Haloalkenyloxy, C_Two
~ C₆Haloalkynyloxy, C ₁~ C_FourAlkylsulf
Enil, C₁~ C_FourAlkylsulfinyl, C₁~ C_FourAl
Killsulfonyl, C_Two~ C₆Alkenylsulfenyl, C
_Two~ C₆Alkenylsulfinyl, C_Two~ C₆Alkenyls
Ruphonyl, C_Two~ C₆Alkynylsulfenyl, C_Two~ C₆
Alkynylsulfinyl, C_Two~ C₆Alkynyl sulfo
Nil, C₁~ C_FourHaloalkylsulfenyl, C₁~ C_FourC
Loalkylsulfinyl, C₁~ C_FourHaloalkyl sulfo
Nil, C_Two~ C₆Haloalkenylsulfenyl, C_Two~ C₆
Haloalkenylsulfinyl, C_Two~ C₆Haloalkenyl
Sulfonyl, C_Two~ C₆Haloalkynylsulfenyl, C
_Two~ C₆Haloalkynylsulfinyl, C_Two~ C₆Haloal
Quinylsulfonyl, NO_Two, CN, -NU¹U^Two, Feno
Kishi, OH, naphthyl, C_Two~ C₇Alkoxycarboni
Le, C_Two~ C_FourAlkoxyalkyl, C_Two~ C_FourAlkylka
Rubonil, C_Two~ C_FiveAlkylcarbonyloxy, C_Two~
C_FiveHaloalkylcarbonyloxy, substituted with X
Benzoyl, phenyl optionally substituted by X
Pyr, pyridyl optionally substituted with X, substituted with X
Optionally thienyl and -N = CT⁷T⁸From within
1 to 4 substituents selected arbitrarily or adjacent positions
5 formed by an alkylene group bonded at an exchange position
An 8-membered ring, Y is halogen, C₁~ C_TenArchi
Le, C₁~ C₆Haloalkyl, C₁~ C₆Alkoxy, C_Two
~ C₆Alkenyloxy, C_Two~ C₆Alkynyloxy,
C₁~ C_FourHaloalkoxy, C_Two~ C₆Haloalkenyloxy
Si, C_Two~ C₆Haloalkynyloxy, C₁~ C_FourAlkyl
Sulfenyl, C₁~ C_FourAlkylsulfinyl, C₁~
C_FourAlkylsulfonyl, C_Two~ C₆Alkenyl sulfe
Nil, C_Two~ C₆Alkenylsulfinyl, C_Two~ C₆Al
Kenylsulfonyl, C_Two~ C₆Alkynylsulfenyl,
C _Two~ C₆Alkynylsulfinyl, C_Two~ C₆Alkynyl
Sulfonyl, C₁~ C_FourHaloalkylsulfenyl, C₁
~ C_FourHaloalkylsulfinyl, C₁~ C_FourHaloalk
Rusulfonyl, C_Two~ C₆Haloalkenylsulfenyl,
C_Two~ C₆Haloalkenylsulfinyl, C_Two~ C₆Haloa
Lucenylsulfonyl, C_Two~ C₆Haloalkynyl sulfe
Nil, C_Two~ C₆Haloalkynylsulfinyl, C_Two~ C₆
Haloalkynylsulfonyl, NO_Two, CN, -NU
¹U^Two, OH, C_Two~ C₇Alkoxycarbonyl, C_Two~ C_Four
Alkoxyalkyl, C_Two~ C_FiveAlkylcarbonyloxy
Si, C_Two~ C_FiveHaloalkylcarbonyloxy, C_Three~ C₇
Dialkylaminocarbonyloxy, substituted with X
Phenyl, and -N = CT⁷T⁸(However, T⁷
And T⁸Is each independently H, phenyl, benzyl or
C₁~ C₆Alkyl or T⁷And T⁸Is combined with
It may form a 5- to 8-membered ring with carbon atoms. )of
1 to 4 substituents arbitrarily selected from or next to
Formed by an alkylene group bonded at the adjacent
G is a halogen, C₁~ C₆
Alkyl, C₁~ C_FourHaloalkyl, C₁~ C_FourAlkoki
Si, C₁~ C_FourHaloalkoxy, C₁~ C_FourAlkylsulf
Enil, C₁~ C_FourAlkylsulfinyl, C₁~ C_FourAl
Killsulfonyl, C₁~ C_FourHaloalkylsulfenyl,
C₁~ C_FourHaloalkylsulfinyl, C₁~ C_FourHaloal
Killsulfonyl, C_Two~ C_FourAlkenyl, C_Two~ C_FourHaloa
Lucenyl, C_Two~ C_FourAlkenyloxy, C_Two~ C_FourHaloa
Lucenyloxy, C_Two~ C_FourAlkenylsulfenyl, C
_Two~ C_FourAlkenylsulfinyl, C_Two~ C_FourAlkenyls
Ruphonyl, C_Two~ C_FourHaloalkenylsulfenyl, C_Two
~ C_FourHaloalkenylsulfinyl, C_Two~ C_FourHaloal
Kenylsulfonyl, C_Two~ C_FourAlkynyl, C_Two~ C_FourHalo
Alkynyl, C_Two~ C_FourAlkynyloxy, C_Two~ C_FourHalo
Alkynyloxy, C_Two~ C_FourAlkynylsulfenyl,
C_Two~ C_FourAlkynylsulfinyl, C_Two~ C_FourAlkynyl
Sulfonyl, C_Two~ C_FourHaloalkynylsulfenyl, C
_Two~ C_FourHaloalkynylsulfinyl, C_Two~ C_FourHaloal
Quinylsulfonyl, NO_Two, CN, formyl, C_Two~ C₆
Alkoxycarbonyl, C_Two~ C_FourAlkylcarbonyl,
C_Two~ C₆Haloalkylcarbonyl, C_Two~ C₆Alkylka
Rubonyloxy and -NU¹U^TwoArbitrarily selected from
1 to 4 substituents;¹Is C₁~ C₂₀Al
Kill, C_Two~ C₆Alkenyl, C₁~ C₆Haloalkyl, C
_Two~ C_FiveAlkoxyalkyl, C_Three~ C₆Halocycloalkyl
Le, R^aC substituted with₁~ C_FourAlkyl, C₁~ C_ThreeAl
C which may be substituted by kill_Three~ C₆Cycloalkyl,
R^aC substituted with_Three~ C₆Cycloalkyl, R^aAnd C
₁~ C_FourCyclopropyl substituted with alkyl, R^cAnd
And halogen-substituted C_Three~ C_FourCycloalkyl group, R
^dAnd C₁~ C_FourCyclopropyl substituted with alkyl
Group, R^aC substituted with_Two~ C_FourAlkenyl, C₁~ C₁₂A
Lucoxy, C₁~ C_FourHaloalkoxy, C_Two~ C_FiveAlkene
Luoxy, C₁~ C_ThreeC optionally substituted with alkyl
_Three~ C₆Cycloalkoxy, benzyloxy, C_Two~ C_FiveA
Lucoxycarbonyl, -NU¹U^Two, Phenylamino, Z
Phenyl optionally substituted with
Phenoxy, phenyl optionally substituted with Z
Thio, naphthyl optionally substituted with Z or
Optionally substituted 5- or 6-membered heterocyclic group (provided that
These heterocyclic groups are thienyl, furyl, pyrrolyl, oxo
Sazolyl, isoxazolyl, thiazolyl, isothiazoly
, Pyrazolyl, imidazolyl, 1,3,4-oxadi
Azolyl, 1,2,4-oxadiazolyl, 1,3,4
Thiadiazolyl, 1,2,4-thiadiazolyl, 1,
2,4-triazolyl, 1,2,3-thiadiazolyl,
1,2,3-triazolyl, 1,2,3,4-tetrazo
Lil, pyridinyl, pyrimidinyl, pyrazinyl, pyrida
Dinyl, 1,3,5-triazinyl and 1,2,4-to
It is selected from riazinil. ) And T^TwoAnd T
^ThreeIs independently OH, phenyl, C₁~ C₆Archi
Le, C₁~ C₆Alkoxy or C₁~ C_FourAlkylsulf
And T^Four, T^FiveAnd T⁶Is independently H,
C₁~ C₆Alkyl, C₁~ C₆Alkenyl, C₁~ C_ThreeAl
C optionally substituted with a kill group_Three~ C₆Cycloalkyl
Group or benzyl, or T^Four, T^FiveAnd T⁶
Two of them share the nitrogen atom to which each is attached.
Contains oxygen, nitrogen or sulfur atoms
X and Z which form a good 5- to 8-membered ring group
Is each independently halogen, C₁~ C_FourAlkyl, C₁
~ C_FourHaloalkyl, C₁~ C_FourAlkoxy, C₁~ C_FourC
Lower alkoxy, C₁~ C_FourAlkylsulfenyl, C₁~
C_FourAlkylsulfinyl, C₁~ C_FourAlkylsulfoni
Le, C_Two~ C_FiveAlkenylsulfenyl, C_Two~ C_FiveArche
Nilsulfinyl, C_Two~ C_FiveAlkenylsulfonyl, C
₁~ C_FourHaloalkylsulfenyl, C₁~ C_FourHaloalk
Rusulfinyl, C₁~ C_FourHaloalkylsulfonyl, N
O_Two, CN, CHO, OH, -NU¹U^Two, Phenyl, f
Enoxy and C_Two~ C_FiveFrom among the alkoxycarbonyl
1 to 5 arbitrarily selected substituents,⁷as well as
T⁸Is independently H, phenyl, benzyl or C₁
~ C₆Alkyl or T⁷And T⁸And combine
May form a 5- to 8-membered ring with the carbon atoms
U¹And U^TwoIs independently H, C₁~ C₆Archi
Le, C_Two~ C_FiveAlkylcarbonyl, C_Two~ C_FiveAlkoxy
Carbonyl, phenyl or benzyl, or U¹When
U^TwoAnd a 5- to 8-membered ring together with the carbon atom to which
R may be formed^aIs halogen and C₁~ C_FourAl
Fe that may be substituted with one or more selected from kills
Nil and R^bIs halogen and C₁~ C_FourAlkyl
Benzoi optionally substituted with at least one member selected from
Yes, R^cIs halogen and C₁~ C_FourAlkoxy
With phenyl optionally substituted by one or more selected from
Yes, R^dRepresents C which may be substituted with halogen_Two~ C
_FourAlkenyl. Acrylonitrification represented by
Compound.

[2] The acrylonitrile compound according to [1], wherein Q is thiazolyl substituted with R. [3] The acrylonitrile compound according to [1], wherein Q is pyrazolyl substituted with R. [4] The acrylonitrile compound according to [1], wherein R is pyrimidinyl or pyrazinyl optionally substituted with G.

[5] An agricultural chemical comprising at least one of the acrylonitrile compounds according to [1] to [4] as an active ingredient.

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION -C (C
The N) = C (OB)-moiety has two isomers, E-form and Z-form, both of which are included in the present invention. When the substituent B in the formula (1) is a hydrogen atom, the compound of the present invention has the formula

[0011]

Embedded image

It will be understood that they may exist in tautomeric forms represented by The compound is thought to exist predominantly in the enol form (1 '), but may under certain conditions take the tautomeric form (2). It is to be understood that the present invention includes all three tautomeric forms and mixtures thereof.

Next, Q, A, B, G, R, Y, W, X,
Preferred ranges of Z, T ¹ , T ² , T ³ , T ⁴ , T ⁵ , T ⁶ , T ⁷ , T ⁸ , U ¹ and U ² will be described. However, the following AI
To AIV, RI to RIII, and T ¹ I to T ¹ III
Has the following meaning. That is, thienyl is a thiophen-2-yl group or a thiophen-3-yl group, and furyl is a furan-2-yl group or a furan-2-yl group.
A 3-yl group, and pyrrolyl is a pyrrol-1-yl group;
A pyrrol-2-yl group, a pyrrol-3-yl group,
Oxazolyl is an oxazol-2-yl group, an oxazol-4-yl group or an oxazol-5-yl group, and thiazolyl is a thiazol-2-yl group, a thiazol-4-yl group or a thiazol-5-yl group, Imidazolyl is an imidazol-1-yl, imidazol-2-yl or imidazol-4-yl group;
Isoxazolyl is an isoxazol-3-yl group, isoxazol-4-yl group or isoxazol-5-yl group, and isothiazolyl is an isothiazol-3-yl group, isothiazol-4-yl group or isothiazol-5-yl group. And pyrazolyl is a pyrazol-1-yl group, a pyrazol-3-yl group, a pyrazol-4-yl group or a pyrazol-5-yl group, and 1,3,4-
Oxadiazolyl is 1,3,4-oxadiazole-2
-Yl group; 1,3,4-thiadiazolyl is 1,1
3,4-thiadiazol-2-yl group;
4-oxadiazolyl is a 1,2,4-oxadiazol-3-yl group or 1,2,4-oxadiazole-5
-Yl group, and 1,2,4-thiadiazolyl is 1,
2,4-thiadiazol-3-yl group or 1,2,4
-Thiadiazol-5-yl group, 1,2,4-triazolyl is 1,2,4-triazol-1-yl group,
1,2,4-triazol-3-yl group or 1,2,2
4-triazol-4-yl and 1,2,3-thiadiazolyl are 1,2,3-thiadiazol-4-yl or 1,2,3-thiadiazol-5-yl; , 3-Triazolyl is a 1,2,3-triazol-1-yl group, a 1,2,3-triazol-2-yl group or a 1,2,3-triazol-4-yl group, 3,4-tetrazolyl is 1,2,3,4-
A tetrazol-1-yl group, a 1,2,3,4-tetrazol-2-yl group or a 1,2,3,4-tetrazol-5-yl group, and pyridinyl is a pyridin-2-yl group, a pyridine- A 3-yl group or a pyridin-4-yl group, pyrimidinyl is a pyrimidin-2-yl group, a pyrimidin-4-yl group or a pyrimidin-5-yl group, and pyrazinyl is a pyrazin-2-yl group; Pyridazinyl is a pyridazin-3-yl group or pyridazin-4
-Yl group, 1,3,5-triazinyl is 1,3
A 5-triazin-2-yl group; 1,2,4-triazinyl is a 1,2,4-triazin-3-yl group;
It is a 2,4-triazin-5-yl group or a 1,2,4-triazin-6-yl group.

Preferred ranges of A are the following groups. AI: phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl,
1,2,3-thiadiazolyl, pyridinyl, pyrimidinyl, pyrazinyl and pyridazinyl.

AII: phenyl, thiazolyl, pyrazolyl, pyridinyl and pyrimidinyl. AIII: Thiazolyl, pyrazolyl and pyridinyl. AIV: Thiazolyl.
AV: pyrazolyl. AVI: pyridinyl. Preferred ranges of B are the following groups. _{That, BI: H, C 1 ~C} 4
Substituted with at least one selected from alkyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₄ alkoxyalkyl, CH ₃ OC ₂ H ₄ OCH ₂ , C ₁ -C ₄ alkylsulfonyl, halogen and C ₁ -C ₄ alkyl Phenylsulfonyl, -SO ₂ CF ₃ , C ₂ -C ₈ dialkylaminosulfonyl, C ₃ -C ₉ dialkylaminothiocarbonyl, C _3-
C ₉ alkoxycarbonylalkyl, —C (＝ O) T ¹ ,
^{-P (= O) T 2 T} 3, -P (= S) T 2 T 3, an alkali metal atom, an alkaline earth metal atom and NHT ⁴ T ⁵ T ^6.

BII: H, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₄ alkoxyalkyl, CH ₃ OC _{2
H 4 OCH 2, C 1 ~C} 4 alkylsulfonyl, -SO ₂ C
_{F 3, -C (= O)} T 1, alkali metal atom, an alkaline earth metal atom and NHT ⁴ T ⁵ T ^6. BIII: H, C ₂ -C ₄
Alkoxyalkyl, C ₁ -C ₄ alkylsulfonyl, -
_{SO 2 CF 3, -C (=} O) T 1, alkali metal atom, an alkaline earth metal atom and NHT ⁴ T ⁵ T ^6.

BIV: C_Two~ C_FourAlkoxyalkyl, C₁
~ C_FourAlkylsulfonyl, -SO_TwoCF_Three, -C (=
O) T¹, Alkali metal atoms, alkaline earth metal atoms
And NHT^FourT^FiveT⁶. Preferred ranges of G are shown below.
Group. That is, GI: halogen, C₁~ C₆Alkyl,
C_Two~ C_FourAlkenyl, C_Two~ C_FourAlkynyl, C₁~ C_FourC
Lower alkyl, C_Two~ C_FourHaloalkenyl, C_Two~ C_FourHaloa
Lucinyl, C₁~ C_ThreeC optionally substituted with alkyl
_Three~ C₆Cycloalkyl, C ₁~ C₆Alkoxy, C_Two~ C_Four
Alkenyloxy, C_Two~ C_FourAlkynyloxy, C ₁~
C_FourHaloalkoxy, C_Two~ C_FourHaloalkenyloxy,
C_Two~ C_FourHaloalkynyloxy, C₁~ C_FourAlkylsul
Phenyl, C₁~ C_FourAlkylsulfinyl, C ₁~ C_FourA
Rukylsulfonyl, C_Three~ C_FourAlkenylsulfenyl,
C_Three~ C_FourAlkenylsulfinyl, C_Three~ C_FourAlkenyl
Sulfonyl, C_Three~ C_FourAlkynylsulfenyl, C_Three~
C_FourAlkynylsulfinyl, C_Three~ C_FourAlkynylsul
Honyl, C ₁~ C_FourHaloalkylsulfenyl, C₁~ C_Four
Haloalkylsulfinyl, C₁~ C_FourHaloalkylsul
Honyl, C_Three~ C_FourHaloalkenylsulfenyl, C_Three~
C_FourHaloalkenylsulfinyl, C_Three~ C_FourHalo arche
Nylsulfonyl, C_Three~ C_FourHaloalkynylsulfeni
Le, C_Three~ C_FourHaloalkynylsulfinyl, C_Three~ C_FourC
Loalkynylsulfonyl, NO_Two, CN, -NU¹U^Two,
Halogen or C₁~ C _FourEven if substituted with alkyl
Methoxy substituted with good phenyl, C_Two~ C₆Alkoki
Cicarbonyl, C_Two~ C_FourAlkoxyalkyl, C_Two~ C_Four
Alkylcarbonyl, C_Two~ C_FourHaloalkylcarboni
Le, C_Two~ C_FiveAlkylcarbonyloxy, C _Two~ C_FiveHalo
Alkylcarbonyloxy, C_Three~ C₇Dialkylamino
Carbonyloxy, phenyl which may be substituted by Z
Phenoxy optionally substituted with Z, substituted with Z
Optionally substituted benzoyl, optionally substituted with Z
Pyridyl and pyridyloxy optionally substituted with Z
A substituent arbitrarily selected from the group (provided that the substituent is
In the case of two or more, they may be the same or different from each other. )
And the number of the substituents is 1, 2, 3 or 4;
Or an alkylene group bonded at an adjacent
A 5-, 6-, 7- or 8-membered ring formed by
is there.

GII :: halogen, C ₁ -C ₆ alkyl, C
₁ -C ₄ alkoxy, C ₁ -C ₄ alkylsulfenyl, C
₁ -C ₄ alkylsulfinyl, C ₁ -C _{4 ^{alkylsulfonyl, NO 2, -NU 1 U 2}} , C 2 ~C 6 alkoxycarbonyl, C ₂ -C ₅ alkylcarbonyloxy, C ₃ -C ₇ dialkylaminocarbonyloxy And phenyl optionally substituted with Z (however, when the number of the substituents is two or more, they may be the same or different from each other), and the number of the substituents is 1 or 2.

GIII: halogen, C ₁ -C ₆ alkyl, N
Substituents arbitrarily selected from phenyl optionally substituted by O ₂ , —NU ¹ U ² and Z (however, when two or more substituents are present, they may be the same or different from each other) Wherein the number of the substituents is one. Preferred ranges of R are the following groups.

That is, RI: furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,
Pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,2
4-triazolyl, 1,2,3-thiadiazolyl, 1,
2,3-triazolyl, 1,2,3,4-tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,
3,5-triazinyl, 1,2,4-triazinyl, benzothiazolyl, benzimidazolyl, indazolyl,
Benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl.

RII: furyl, pyrrolyl, oxazolyl,
Isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,2
4-thiadiazolyl, 1,2,4-triazolyl, 1,
2,3-thiadiazolyl, 1,2,3-triazolyl,
1,2,3,4-tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,
2,4-triazinyl.

RIII: pyrimidinyl, pyrazinyl. Preferred ranges of R ¹ are the following groups. That is, R ¹ I:
Halogen, C ₁ -C ₅ alkoxycarbonyl, NO _2, C
^{N, -NU 1 U 2, -N} = CT 7 T 8. R ¹ II: halogen,
C ₁ -C ₅ alkoxycarbonyl.

The preferred range of n is nI: 0 or 1, and nII: 0. Preferred ranges of Y are the following groups. That is, YI: halogen, C ₁ -C ₆ alkyl,
C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₂ -C ₄
Alkenyloxy, C ₂ -C ₄ alkynyloxy, C _1-
C ₄ haloalkoxy, C ₂ -C ₄ haloalkenyloxy,
C ₂ -C ₄ haloalkynyloxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₃ -C ₄ alkenyl Le phenyl,
C ₃ -C ₄ alkenylsulfinyl, C ₃ -C ₄ alkenylsulfonyl, C ₃ -C ₄ alkyl Nils Le phenyl, C ₃ ~
C ₄ alkynylsulfinyl, C ₃ -C ₄ alkynylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄
Haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₃ -C ₄ halo alkenyl Le phenyl, C ₃ ~
C ₄ halo alkenylsulfinyl, C ₃ -C ₄ haloalkenyl sulfonyl, C ₃ -C ₄ haloalkylene Nils Le phenyl, C ₃ -C ₄ halo alkynylsulfinyl, C ₃ -C ₄ haloalkynyl sulfonyl, NO _2, CN, -NU ¹ U ² ,
C ₂ -C ₄ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, C ₂ -C ₄ alkylcarbonyloxy, C ₂ -C ₄
A substituent arbitrarily selected from haloalkylcarbonyloxy or phenyl optionally substituted with X (however, when two or more substituents are present, they may be the same or different from each other); The number of substituents is one, two or three.

YII: halogen, C₁~ C_FourAlkyl, C₁
~ C_FourHaloalkyl, C₁~ C_FourAlkoxy, C₁~ C_FourA
Rukylsulfenyl, C₁~ C_FourAlkylsulfinyl,
C₁~ C_FourAlkylsulfonyl, C₁~ C_FourHaloalkyls
Luphenyl, C₁~ C_FourHaloalkylsulfinyl, C₁
~ C_FourHaloalkylsulfonyl, NO_Two, CN, C_Two~ C _Four
Optionally substituted with alkoxycarbonyl or X
A substituent arbitrarily selected from phenyl (however,
When two or more substituents are present, they may be the same or different from each other.
No. ) Wherein the number of the substituents is 1, 2 or 3
is there.

The number of Y differs depending on the type of heterocyclic ring substituted by Y, and the heterocyclic ring is 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,2 4-thiadiazolyl, 1,2,3
In the case of -thiadiazolyl or 1,2,3,4-tetrazolyl, the number of Y is 0 or 1, and preferably 1. The heterocycle is thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,5-triazinyl, 1,2,4- In the case of triazinyl or 1,2,4-triazinyl, the number of Y is an integer of 0 to 2, preferably 1 or 2. When the heterocyclic ring is thienyl, furyl, pyrazolyl, imidazolyl, pyrimidinyl, pyrazinyl or pyridazinyl, the number of Y is an integer from 0 to 3, preferably an integer from 0 to 2, more preferably 1 or 2. is there. When the heterocyclic ring is pyrrolyl or pyridinyl, the number of Y is an integer of 0 to 4, preferably 0 to 3.
And more preferably 1 or 2.

Preferred ranges of W are the following groups.
You. That is, WI: halogen, C₁~ C₆Alkyl, C₁~ C
_FourHaloalkyl, C₁~ C_FourAlkoxy, C₁~ C_FourHaloa
Lucoxy, C₁~ C_FourAlkylsulfenyl, C₁~ C_FourA
Rukylsulfinyl, C₁~ C_FourAlkylsulfonyl, C
₁~ C_FourHaloalkylsulfenyl, C₁~ C_FourHaloalk
Rusulfinyl, C₁~ C_FourHaloalkylsulfonyl, C
_Three~ C_FourAlkenyloxy, C_Three~ C_FourHaloalkenyloxy
Si, C_Three~ C_FourAlkenylsulfenyl, C_Three~ C_FourArche
Nilsulfinyl, C_Three~ C_FourAlkenylsulfonyl, C
_Three~ C_FourHaloalkenylsulfenyl, C_Three~ C_FourHaloal
Kenylsulfinyl, C_Three~ C_FourHaloalkenylsulfoni
Le, C_Three~ C_FourAlkynyloxy, C_Three~ C_FourAlkynyls
Luphenyl, C_Three~ C_FourAlkynylsulfinyl, C _Three~
C_FourAlkynylsulfonyl, NO_Two, CN, C_Two~ C_FourAl
Coxycarbonyl, C_Two~ C_FourAlkylcarbonyl, C_Two
~ C_FourHaloalkylcarbonyl, C_Two~ C_FourAlkyl cal
Bonyloxy and -NU¹U^TwoArbitrarily selected from among
Groups (however, when the substituents are two or more,
May be different. ) Wherein the number of the substituents is 1,
2, 3, or 4.

WII: halogen, C ₁ -C ₄ alkyl, C ₁
-C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ ~
C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₃ -C ₄ alkenyloxy, C ₃ -C ₄ haloalkenyloxy, C ₃ -C ₄ alkenyl Le phenyl, C ₃ -C ₄
Alkenylsulfinyl, C ₃ -C ₄ alkenylsulfonyl, C ₃ -C ₄ alkynyloxy, C ₃ -C ₄ alkyl Nils Le phenyl, C ₃ -C ₄ alkynylsulfinyl, C ₃ ~
A substituent arbitrarily selected from C ₄ alkynylsulfonyl, NO ₂ and CN (however, when the number of the substituents is two or more, they may be the same or different from each other); The number is one, two or three.

WIII: halogen, C ₁ -C ₄ alkyl, C ₁
-C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ ~
C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, selected C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, NO _2, CN, from among optionally Substituents (however, when the number of the substituents is two or more, they may be the same or different from each other), and the number of the substituents is one or two.

Preferred ranges of T ¹ are the following groups. _{^{That, T 1 I: C 1 ~C}} 18 alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy -C
₁ -C ₄ alkyl, halogen or C ₁ -C ₄ alkyl C ₁ -C ₄ alkyl substituted with phenyl optionally substituted, C ₃ -C ₆ halocycloalkyl, optionally substituted with C ₁ -C ₃ alkyl which may C ₃ -C ₆ cycloalkyl optionally halogen or C ₁ -C ₄ alkyl substituted with phenyl which is substituted C ₃ -C ₆ cycloalkyl, halogen or C ₁ -C ₄ alkyl group in substituted with phenyl which is substituted C ₂ -C ₄ alkenyl, C ₁ -C
₁₀ alkoxy, C ₁ -C ₄ haloalkoxy, C ₃ -C ₅ alkenyloxy, C ₃ -C ₆ cycloalkoxy optionally substituted by C ₁ -C ₃ alkyl, benzyloxy, C ₂ -C ₅
C ₅ alkoxycarbonyl, -NU ¹ U ^2, which may be substituted with Z phenyl, optionally substituted by Z, phenoxy, optionally substituted by Z, phenylthio, optionally substituted naphthyl or Z Good heterocyclic group (however,
This heterocyclic group is thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4
-Oxadiazolyl, 1,3,4-thiadiazolyl,
1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl,
Pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5
-Selected from among triazinyl or 1,2,4-triazinyl. ).

T¹II: C₁~ C₁₈Alkyl, C_Two~ C₆Al
Kenil, C₁~ C_FourHaloalkyl, C _Two~ C_FourAlkoxya
Lucyl, halogen or C₁~ C_FourSubstituted with alkyl
Optionally substituted with phenyl₁~ C_FourAlkyl,
C₁~ C_ThreeC optionally substituted with alkyl_Three~ C₆Shiku
Loalkyl, halogen or C₁~ C_FourSubstitute with alkyl
Optionally substituted phenyl substituted C_Three~ C₆Cyclo
Alkyl, halogen or C₁~ C_FourSubstitute with alkyl group
Optionally substituted phenyl substituted C_Two~ C_FourArche
Nil, C₁~ C_TenAlkoxy, C₁~ C_FourHaloalkoki
Si, C_Three~ C_FiveAlkenyloxy, C_Three~ C₆Cycloalco
Xy, benzyloxy, C_Two~ C_FiveAlkoxycarboni
Phenyl optionally substituted with Z, substituted with Z
Phenoxy, phenylthio, naphthyl or
Is a heterocyclic group optionally substituted by Z (provided that the heterocyclic group
The ring group is thienyl, furyl, oxazolyl, thiazolyl,
It is selected from pyrazolyl or pyridinyl. )
You.

T ¹ III: C ₁ -C ₁₇ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₄ alkoxyalkyl, C ₁ -C ₄ alkyl substituted with phenyl, C ₁ -C ₄ alkyl
₁ -C ₃ alkyl optionally substituted C ₃ -C ₆ cycloalkyl, cycloalkyl substituted with phenyl, C ₂ -C ₄ alkenyl substituted with phenyl, C ₁ -C ₈ alkoxy, C ₁ ~ C ₄ haloalkoxy, C ₃ -C ₅ alkenyloxy, C ₃ -C ₆ cycloalkoxy, benzyloxy, C
₂ -C ₅ alkoxycarbonyl, a Z with phenyl optionally substituted, may be substituted with Z phenoxy, phenylthio, naphthyl, pyrazolyl or pyridinyl optionally substituted by Z.

The preferred range of T ² is the following group. That is, T ² I: phenyl, C ₁ -C ₄ alkyl, C _1-
C ₄ alkoxy or C ₁ -C ₄ alkylsulphenyl. Preferred ranges of T ³ are the following groups. That is, T ³ I is phenyl, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy or C ₁ -C ₄ alkylsulfenyl.

The preferred range of T ⁴ is the following group. That is, T ⁴ I: H, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl or benzyl, or T ⁴ ,
Two of T ⁵ and T ⁶ together with the nitrogen atom to which each is attached form a 5-, 6- or 7-membered ring group which may contain an oxygen, nitrogen or sulfur atom Is what you do.

The preferred range of T ⁵ is the following group. That is, T ⁵ I: H, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl or benzyl, or T ⁴ ,
Two of T ⁵ and T ⁶ together with the nitrogen atom to which each is attached form a 5-, 6- or 7-membered ring group which may contain an oxygen, nitrogen or sulfur atom Is what you do.

The preferred range of T ⁶ is the following group. That is, T ⁶ I: H, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl or benzyl, or T ⁴ ,
Two of T ⁵ and T ⁶ together with the nitrogen atom to which each is attached form a 5-, 6- or 7-membered ring group which may contain an oxygen, nitrogen or sulfur atom The preferable range of X is each group shown below.

That is, XI: halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁
-C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₃ -C ₅ alkenyl Le phenyl, C ₃ ~
C ₅ alkenylsulfinyl, C ₃ -C ₅ alkenylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄
Haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, NO _2, CN, -NU ¹ U ^2, or C ₂ -C ₅ alkoxy optionally selected substituents from the carbonyl (when the substituent is two or more May be the same or different from each other), and the number of the substituents is 1, 2, or 3.

XII: halogen, C ₁ -C ₄ alkyl, C ₁
-C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ ~
C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₃ -C ₅ alkenyl Le phenyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, the NO ₂ A substituent arbitrarily selected from among them (however, when the number of the substituents is two or more, they may be the same or different from each other), and the number of the substituents is 1, 2, or 3.

XIII: halogen, C ₁ -C ₄ alkyl, C ₁
To C ₄ haloalkyl and C _{1 to} C ₄ alkoxy, which are arbitrarily selected (provided that when two or more substituents are present, they may be the same or different from each other); The number of groups is one or two. The number of X varies depending on the ring substituted by X. When the ring is phenyl, the number of X is an integer of 0 to 5, preferably 0 to 3. When the ring is pyridyl, the number of X is an integer of 0 to 4, preferably 0, 1 or 2, and more preferably 0 or 1. In the case of a thienyl group, the number of X is an integer of 0 to 3, preferably 0 or 1.

Preferred ranges of Z are the following groups. That is, ZI: halogen, C ₁ -C ₄ alkyl, C ₁ -C
₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C
₃ -C ₅ alkenyl Le phenyl, C ₃ -C ₅ alkenylsulfinyl, C ₃ -C ₅ alkenylsulfonyl, C ₁ -C ₄
Haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, NO _2,
A substituent arbitrarily selected from CN, -NU ¹ U ² or C ₂ -C ₅ alkoxycarbonyl (provided that the substituent is 2
In the case of two or more, they may be the same or different from each other. ) Wherein the number of the substituents is 1, 2, 3 or 4.

ZII: halogen, C₁~ C_FourAlkyl, C₁
~ C_FourHaloalkyl, C₁~ C_FourAlkoxy, C₁~ C_FourC
Lower alkoxy, C₁~ C_FourAlkylsulfenyl, C₁~
C_FourAlkylsulfinyl, C₁~ C_FourAlkylsulfoni
Le, C_Three~ C_FiveAlkenylsulfenyl, C_Three~ C_FiveArche
Nilsulfinyl, C_Three~ C_FiveAlkenylsulfonyl, C
₁~ C_FourHaloalkylsulfenyl, C₁~ C_FourHaloalk
Rusulfinyl, C₁~ C _FourIn haloalkylsulfonyl
A substituent arbitrarily selected from the group consisting of two or more
In the above case, they may be the same or different. )
The number of the substituents is one, two, three or four.

The number of Z differs depending on the type of ring substituted by Z. When the ring substituted by Z is phenyl, the number of Z is 0.
To 5, preferably 0 to 4, and more preferably 0, 1, 2, or 3. When the ring substituted by Z is naphthyl, the number of Z is an integer of 0 to 7, and preferably 0. When the ring substituted by Z is a heterocyclic group, the number of Z differs depending on the heterocyclic ring, and the heterocyclic ring is 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,
4-thiadiazolyl, 1,2,3-oxadiazolyl,
In the case of 1,2,3-thiadiazolyl, 1,2,3,4-tetrazolyl or 1,2,3,5-tetrazolyl, the number of Z is 0 or 1. The heterocycle is thiazolyl,
Oxazolyl, isoxazolyl, isothiazolyl,
1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl or 1,2,4-triazinyl Is the number of Z is an integer from 0 to 2,
Preferably it is 1 or 2. The heterocycle is thienyl,
In the case of furyl, pyrazolyl, imidazolyl, pyrimidinyl, pyrazinyl or pyridazinyl, the number of Z is an integer from 0 to 3, preferably an integer from 0 to 2, and more preferably 1 or 2. When the heterocyclic ring is pyrrolyl or pyridinyl, the number of Z is an integer of 0 to 4, preferably an integer of 0 to 2, and more preferably 1 or 2.

Preferred ranges of T ⁷ are the following groups. That is, T ⁷ I: H, phenyl, benzyl or C _1-
It is C ₄ alkyl or forms a 5- or 6-membered ring with the carbon atom to which T ⁷ and T ⁸ are attached. Preferred ranges of T ⁸ are the following groups. That is, T ⁸ I:
Phenyl, benzyl or C ₁ -C ₄ alkyl, or
Alternatively T ⁷ and the T ⁸ to form a 5- or 6-membered ring together with the carbon atom bonded.

Preferred ranges of U ¹ are the following groups. That is, U ¹ I: H, C ₁ -C ₄ alkyl or C ₂ -C ₅
It may be an alkylcarbonyl or form a 5-, 6-, or 7-membered ring with the carbon atom to which U ¹ and U ² are bonded. Preferred ranges of U ² are the following groups.

That is, U ² I: H, C ₁ -C ₄ alkyl or C ₂ -C ₅ alkylcarbonyl, or a 5-membered ring or a 6-membered ring together with the carbon atom to which U ¹ and U ² are bonded. , A 7-membered ring.

Each group in the above-mentioned preferred substituents can be arbitrarily combined, and particularly preferred compounds of the present invention are listed below. That is, the preferred substituent ranges are AI, BI, GI, RI, R ¹ I, nI, YI,
WI, T ¹ I, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XI, Z
^{I, T 7 I, T 8} I, a compound of the invention which is U ¹ I and U ² I.

The preferred range of the substituent is AII, BI, GI
^{I, RI, R 1 II,} nI, YI, WI, T 1 I, T 2 I, T 3 I, T
^The compound of the present invention, which is ⁴ I, T ⁵ I, T ⁶ I, XI, ZI, T ⁷ I, T ⁸ I, U ¹ I and U ² I. Preferred substituent ranges are AII, B
I, GIII, RI, nII, YI, WI, T ¹ I, T ² I, T ³ I,
^{T 4 I, T 5 I,} T 6 I, XI, ZI, T 7 I, T 8 I, U 1 I and U ² I
A compound of the present invention which is

The preferred range of the substituent is AIII, BI, GII
I, RI, nII, YI, T ¹ I, T ² I, T ³ I, T ⁴ I, T ⁵ I,
The compound of the present invention, which is T ⁶ I, XI, ZI, T ⁷ I, T ⁸ I, U ¹ I and U ² I. Preferred substituent ranges are AIII, BII, GII,
^{RII, R 1 II, nI,} YII, T 1 II, T 2 I, T 3 I, T 4 I,
The compound of the present invention, which is T ⁵ I, T ⁶ I, XII, ZII, T ⁷ I, T ⁸ I, U ¹ I and U ² I.

Preferred ranges of the substituents are AIII, BIII, G
III, RIII, R¹II, nI, YII, T ¹III, T^TwoI, T^ThreeI,
T^FourI, T^FiveI, T⁶I, XIII, ZII, T⁷I, T⁸I, U¹I and
U^TwoA compound of the present invention which is I. The preferred substituent range is AII
I, BIII, GIII, RIII, nII, YII, T¹III, T^TwoI,
T^ThreeI, T^FourI, T^FiveI, T⁶I, XIII, ZII, T⁷I, T⁸I,
U¹I and U^TwoA compound of the present invention which is I.

The preferred range of the substituent is AIV, BIII, GI
II, RIII, nII, YII, T¹III, T^TwoI, T^ThreeI, T^FourI,
T^FiveI, T⁶I, XIII, ZII, T⁷I, T⁸I, U¹I and U^TwoIn i
Certain compounds of the present invention. Preferred ranges of the substituents are AIV, BI
V, GIII, RIII, nII, YII, T¹III, T ^TwoI, T^ThreeI,
T^FourI, T^FiveI, T⁶I, XIII, ZII, T⁷I, T⁸I, U¹I and
U^TwoA compound of the present invention which is I.

The preferred range of the substituent is AIV, BIV, GII
I, RIII, nII, YII, T¹III, T ^TwoI, T^ThreeI, T^FourI, T
^FiveI, T⁶I, XIII, ZII, T⁷I, T⁸I, U¹I and U^TwoI
The compound of the present invention. Preferred substituent ranges are AV, BIII,
GIII, RIII, nII, YII, T¹III, T ^TwoI, T^ThreeI, T
^FourI, T^FiveI, T⁶I, XIII, ZII, T⁷I, T⁸I, U¹I and U^Two
A compound of the present invention which is I.

Preferred substituent ranges are AV, BIV and GII.
I, RIII, nII, YII, T 1 III, T 2 I, T 3 I, T 4 I, T
^The compound of the present invention which is ⁵ I, T ⁶ I, XIII, ZII, T ⁷ I, T ⁸ I, U ¹ I or U ² I. Preferred substituent ranges are AV, BIV,
GIII, RIII, nII, YII, T 1 III, T 2 I, T 3 I, T
⁴ I, T ⁵ I, T ⁶ I, XIII, ZII, T ⁷ I, T ⁸ I, U ¹ I and U ²
A compound of the present invention which is I. The preferred substituent range is AVI,
BIII, GIII, RIII, nII, YII, T 1 III, T 2 I, T 3
I, T ⁴ I, T ⁵ I, T ⁶ I, XIII, ZII, T ⁷ I, T ⁸ I, U ¹ I
And the compound of the present invention, which is U ² I.

The preferred range of the substituent is AVI, BIV, GII
I, RIII, nII, YII, T¹III, T ^TwoI, T^ThreeI, T^FourI, T
^FiveI, T⁶I, XIII, ZII, T⁷I, T⁸I, U¹I and U^TwoI
The compound of the present invention. Preferred substituent ranges are AVI, BIV,
GIII, RIII, nII, YII, T¹III, T ^TwoI, T^ThreeI, T
^FourI, T^FiveI, T⁶I, XIII, ZII, T⁷I, T⁸I, U¹I and U^Two
A compound of the present invention which is I.

Next, Q, A, B, G, R, R ¹ , Y, W,
^{X, Z, T 1, T} 2, T 3, T 4, T 5, T 6, T 7, T 8, U
Examples of each atom and group in the definition of ¹ or U ² are shown.
Examples of the halogen atom in the definition of G, R ¹ , W, X, Y or Z include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and preferably a fluorine atom, a chlorine atom and a bromine atom.

B, G, T ¹ , T ² , T ³ , T ⁴ , T ⁵ , T ⁶ ,
Examples of the alkyl group in the definition of T ⁷ , T ⁸ , U ¹ , U ² , W, X, Y or Z include a linear or branched alkyl group such as methyl, ethyl, n-propyl, isopropyl,
n-butyl, isobutyl, tert-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-dimethyl Butyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1
-Methylpropyl, 1-ethyl-2-methylpropyl,
n-heptyl, n-octyl, n-nonyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n- Icosyl and the like are listed, and each is selected in the range of the specified number of carbon atoms.

In the definition of G, T ¹ , T ⁴ , T ⁵ , T ⁶ or W, the alkenyl group may be a straight-chain or branched alkenyl group such as ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, -Butenyl, 3-butenyl, 1
-Methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-
Methyl-2-butenyl, 3-methyl-2-butenyl, 1
-Methyl-3-butenyl, 2-methyl-3-butenyl,
3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4- Hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-
2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl,
4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-
Pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-2-butenyl,
1,3-dimethyl-3-butenyl, 2,3-dimethyl-
2-butenyl, 2,3-dimethyl-3-butenyl, 3,
3-dimethyl-2-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2- Propenyl, 1-ethyl-1-methyl-2-
And propenyl and the like, and each is selected from the specified carbon number range.

The alkynyl group in the definition of G or W includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, and alkynyl groups which are linear or branched.
2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-
Methyl-3-butynyl, 2-methyl-3-butynyl, hexynyl, 1-methyl-3-pentynyl, 1-methyl-
4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl,
4-methyl-2-pentynyl, 1,1-dimethyl-2-
Butynyl, 1,1-dimethyl-3-butynyl, 1,2-
Dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and the like; Is selected from the range.

The haloalkyl group in the definition of B, G, T ¹ , W, X, Y or Z is a straight-chain or branched haloalkyl group such as fluoromethyl group, chloromethyl group, bromomethyl group, fluoroethyl group, chloroethyl group. Group, bromoethyl group, fluoro-n-propyl group, chloro-n-propyl group, difluoromethyl group, chlorodifluoromethyl group, trifluoromethyl group, dichloromethyl group, trichloromethyl group, difluoroethyl group, trifluoroethyl group, Trichloroethyl, chlorodifluoromethyl, bromodifluoromethyl, trifluorochloroethyl, hexafluoro-n-propyl, chlorobutyl, fluorobutyl, chloro-n-pentyl, fluoro-n-pentyl, chloro -N-hexyl group, fluoro- - hexyl group and the like, is selected from the range of the specified number of carbon.

[0058] ^{W, T 1, T 4,} T in the definition of ⁵ or T ^6, C ₁ ^~C ₃ alkyl C ₃ optionally substituted by -C ₆
As cycloalkyl, a cyclopropyl group, a 1-methylcyclopropyl group, a 2,2,3,3-tetramethylcyclopropyl group, a cyclobutyl group, a 1-ethylcyclobutyl group, a 1-n-butylcyclobutyl group, Examples thereof include a cyclopentyl group, a 1-methylcyclopentyl group, a cyclohexyl group, a 1-methylcyclohexyl group, and a 4-methylcyclohexyl group.

In the definition of B, W or T ¹ , the C ₁ -C ₄ alkyl group substituted by ^Ra is benzyl, 2
-Chlorobenzyl group, 3-bromobenzyl group, 4-chlorobenzyl group, 4-methylbenzyl group, 4-tert-butylbenzyl group, 1-phenylethyl group, 1- (3
-Chlorophenyl) ethyl group, 2-phenylethyl group,
1-methyl-1-phenylethyl group, 1- (4-chlorophenyl) -1-methylethyl group, 1- (3-chlorophenyl) -1-methylethyl group, 1-phenylpropyl group, 2-phenylpropyl group, 3-phenylpropyl group, 1-phenylbutyl group, 2-phenylbutyl group, 3
-Phenylbutyl group, 4-phenylbutyl group, 1-methyl-1-phenylpropyl group, 1-methyl-2-phenylpropyl group, 1-methyl-3-phenylpropyl group,
2-methyl-2-phenylpropyl group, 2- (4-chlorophenyl) -2-methyl-propyl group, 2-methyl-
And a 2- (3-methylphenyl) propyl group.

C ₃ substituted for R ^a in the definition of T ¹
-C ₆ cycloalkyl group includes 1-phenylcyclopropyl group, 1- (3-chlorophenyl) cyclopropyl group, 1- (4-chlorophenyl) cyclopropyl group,
1- (4-bromophenyl) cyclopropyl group, 1-
(4-fluorophenyl) cyclopropyl group, 1- (4
-Ethylphenyl) cyclopropyl group, 1- (4-propylphenyl) cyclopropyl group, 2-phenylcyclopropyl group, 1-phenylcyclobutyl group, 2-phenylcyclobutyl group, 1-phenylcyclopentyl group, 1
-(4-chlorophenyl) cyclopentyl group, 2-phenylcyclopentyl group, 3-phenylcyclopentyl group, 1-phenylcyclohexyl group, 1- (3-fluorophenyl) cyclohexyl group, 1- (4-chlorophenyl) cyclohexyl group, 1 -(4-tert-butylphenyl) cyclohexyl, 2-phenylcyclohexyl, 3-phenylcyclohexyl, 4-phenylcyclohexyl and the like.

In the definition of T ¹ , the cyclopropyl group substituted by R ^a and a C ₁ -C ₄ alkyl group includes 2,2.
2-dimethyl-1-phenylcyclopropyl group, 1-
(4-chlorophenyl) -2,2-dimethylcyclopropyl group, 2,2-dimethyl-3-phenylcyclopropyl group, 3- (3-chlorophenyl) -2,2-dimethylcyclopropyl group, (4-chlorophenyl) −2,2-
Dimethyl-3-phenylcyclopropyl group, (4-bromophenyl) -2,2-dimethyl-3-phenylcyclopropyl group, 2,2-dimethyl-3- (4-methylphenyl) cyclopropyl group, (4- (Tert-butylphenyl) -2,2-dimethyl-3-phenylcyclopropyl group.

In the definition of T ¹ , R ³ and a C ₃ -C ₄ cycloalkyl group substituted by a halogen atom include:
2,2-dichloro-1-phenylcyclopropyl group,
2,2-dichloro-1- (3-chlorophenyl) cyclopropyl group, 2,2-dichloro-1- (4-methoxyphenyl) cyclopropyl group, 2,2-dichloro-1-
(4-ethoxyphenyl) cyclopropyl group, 2,2-
Dichloro-1- (4-i-propyloxyphenyl) cyclopropyl group, 2,2-dichloro-1- (4-t-butylphenyl) cyclopropyl group, 2,2-dichloro-
1- (4-methoxyphenyl) -3-phenylcyclopropyl group, 1- (4-ethoxyphenyl) -2,2,
And a 3,3, -tetrafluorobutyl group.

In the definition of T ¹ , the cyclopropyl group substituted by R ^c and a C ₁ -C ₄ alkyl group includes 2,2
2-dimethyl-3- (2,2-dimethylethenyl) cyclopropyl group, 3- (2,2-dibromoethenyl)-
2,2-dimethylcyclopropyl group, 3- (2,2-dichloroethenyl) -2,2-dimethylcyclopropyl group, 3- (2,2-chlorotrifluoroethenyl)-
Examples include a 2,2-dimethylcyclopropyl group.

The C ₃ -C ₆ cycloalkoxy group which may be substituted with a C ₁ -C ₃ alkyl group in the definition of T ¹ includes cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexyloxy, And a 1-methylcyclopropoxy group. In the definition of T ^1,
The C ₂ -C ₄ alkenyl group substituted by R ^a includes 1
-Phenylethenyl group, 2-phenylethenyl group, 2-
(2-chlorophenyl) ethenyl group, 2- (3-chlorophenyl) ethenyl group, 2- (4-chlorophenyl) ethenyl group, 2- (4-methylphenyl) ethenyl group, 2
-(2,6-difluorophenyl) ethenyl group, 2-
(2,5-dimethylphenyl) ethenyl group, 1-methyl-2-phenylethenyl group, 2-phenyl-1-propenyl group, 2- (4-bromophenyl) -1-propenyl group, 2- (2 4,6-trimethylphenyl) -1-propenyl group.

G, T ¹ , T ² , T ³ , W, X, Y or Z
Examples of the alkoxy group in the definition of are methoxy, ethoxy, n
-A propoxy group, an isopropoxy group, an n-butoxy group,
Isobutoxy group, sec-butoxy group, tert-butoxy group, n-pentyloxy group, 1-methylbutyloxy group, 2-methylbutyloxy group, 3-methylbutyloxy group, 1,1-dimethylpropoxy group, 2-dimethylpropoxy group, 2,2-dimethylpropoxy group, 1
-Ethylpropyloxy group, n-hexyloxy group, 1
-Methylpentyloxy group, 2-methylpentyloxy group, 3-methylpentyloxy group, 4-methylpentyloxy group, 1,1-dimethylbutyloxy group, 1,2-
Dimethylbutyloxy group, 1,3-dimethylbutyloxy group, 2,2-dimethylbutyloxy group, 2,3-dimethylbutyloxy group, 3,3-dimethylbutyloxy group, 1-ethylbutyloxy group, 2- Ethylbutyloxy group, 1,1,2-trimethylpropyloxy group, 1,
2,2-trimethylpropyloxy group, 1-ethyl-1
-Methylpropyloxy group and 1-ethyl-2-methylpropyloxy group, n-heptyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group and the like. Selected from a range.

3 to 6 carbon atoms in the definition of W or T ¹
Examples of the halocycloalkyl group include fluorocyclopropyl, difluorocyclopropyl, chlorocyclopropyl, dichlorocyclopropyl, 1-methyl-
Examples thereof include a 2,2-dichlorocyclopropyl group, a chlorocyclobutyl group, a dichlorocyclobutyl group, a chlorocyclopentyl group, a dichlorocyclopentyl group, a chlorocyclohexyl group, a dichlorocyclohexyl group, and a tetrafluorocyclobutyl group.

In the definition of G, R ¹ , T ¹ , W, X, Y or Z, —NU ¹ U ² represents methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino. Group, sec
-Butylamino group, tert-butylamino group, n-pentylamino group, 1-methylbutylamino group, 2-methylbutylamino group, 3-methylbutylamino group, 1,1
-Dimethylpropylamino group, 1,2-dimethylpropylamino group, 2,2-dimethylpropylamino group, 1-
Ethylpropylamino group, n-hexylamino group, 1-
Methylpentylamino group, 2-methylpentylamino group, 3-methylpentylamino group, 4-methylpentylamino group, 1,1-dimethylbutylamino group, 1,2-
Dimethylbutylamino group, 1,3-dimethylbutylamino group, 2,2-dimethylbutylamino group, 2,3-dimethylbutylamino group, 3,3-dimethylbutylamino group, 1-ethylbutylamino group, 2- Ethylbutylamino group, 1,1,2-trimethylpropylamino group, 1,
2,2-trimethylpropylamino group, 1-ethyl-1
-Methylpropylamino group and 1-ethyl-2-methylpropylamino group, dimethylamino group, diethylamino group, di-n-propylamino group, diisopropylamino group, di-n-butylamino group, di-sec-butylamino Group, diisobutylamino group, di-n-pentylamino group, di-n-hexylamino group, methylethylamino group, methylpropylamino group, methylisopropylamino group, methylbutylamino group, methyl-sec-butylamino group, Methyl isobutylamino group, methyl-ter
t-butylamino group, methylpentylamino group, methylhexylamino group, ethylpropylamino group, ethylisopropylamino group, ethylbutylamino group, ethyl-
sec-butylamino group, ethylisobutylamino group,
Ethylpentylamino group, ethylhexylamino group, phenylamino group, benzylamino group, N-methylacetamido group, N-ethylacetamido group, N-phenylacetamido group, N-acetylacetamido group, etc. It is selected in a range of numbers.

The alkoxycarbonyl group in the definition of G, R ¹ , T ¹ , W, X, Y and Z includes methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, iso-propoxycarbonyl, n-butoxy Carbonyl group, sec-butoxycarbonyl group, i
Examples thereof include a so-butoxycarbonyl group, a tert-butoxycarbonyl group, an n-pentyloxycarbonyl group, an n-hexyloxycarbonyl group and the like.

The C ₁ -C ₄ haloalkoxy groups in the definitions of G, T ¹ , W, X, Y and Z each have 1 to 1 carbon atoms.
4, straight-chain or branched-chain haloalkoxy groups, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, dichlorofluoromethoxy, chloromethoxy, and dichloromethoxy groups. Methoxy, trichloromethoxy, bromomethoxy, fluoroethoxy, chloroethoxy, bromoethoxy, difluoroethoxy, trifluoroethoxy, tetrafluoroethoxy, pentafluoroethoxy, trichloroethoxy, trifluorochloroethoxy Group, fluoropropoxy group, chloropropoxy group, bromopropoxy group, fluorobutoxy group, chlorobutoxy group, fluoro-iso-propoxy group and chloro-iso-propoxy group. .

The C ₁ -C ₄ alkylsulfenyl groups in the definitions of G, T ² , T ³ , W, X, Y and Z include methylthio, ethylthio, n-propylthio and iso.
-Propylthio group, n-butylthio group, iso-butylthio group, sec-butylthio group, and tert-butylthio group. C in the definition of G, X, W, Y and Z
Examples of the ₁ to ₄ alkylsulfinyl groups include a methylsulfinyl group, an ethylsulfinyl group, an n-propylsulfinyl group, an iso-propylsulfinyl group, an n-butylsulfinyl group, an iso-butylsulfinyl group, and s.
and an ec-butylsulfinyl group and a tert-butylsulfinyl group.

The C ₁ -C ₄ alkylsulfonyl groups in the definitions of B, G, W, X, Y and Z include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, iso-propylsulfonyl, n- Examples thereof include a butylsulfonyl group, an iso-butylsulfonyl group, a sec-butylsulfonyl group, and a tert-butylsulfonyl group.

Carbon number 2 in the definition of W, T ¹ or Y
Examples of the alkoxyalkyl group having 4 to 4 include an alkoxy-methyl group having 1 to 3 carbon atoms, an alkoxy-ethyl group having 1 to 2 carbon atoms, a methoxyethoxymethyl group and a methoxypropyl group. Examples of the alkylcarbonyl group having 2 to 4 carbon atoms in the definition of G, U ¹ , U ² or W include an acetyl group, a propionyl group, a butanoyl group, and is
o-butanoyl group.

Examples of the haloalkylcarbonyl group having 2 to 6 carbon atoms in the definition of G include a chloroacetyl group, a trifluoroacetyl group, a 3,3,3-trifluoropropionyl group and a pentafluoropropionyl group. Examples of the haloalkylcarbonyloxy group having 2 to 5 carbon atoms in the definition of W include a chloroacetyloxy group, a trifluoroacetyloxy group, a 3,3,3-trifluoropropionyloxy group, and a pentafluoropropionyloxy group.

The dialkylaminocarbonyloxy group having 3 to 7 carbon atoms in the definition of Y includes a dimethylaminocarbonyloxy group, a diethylaminocarbonyloxy group, a di-propylaminocarbonyloxy group and the like. The naphthyl group in the definition of A, W and T ¹ includes a 1-naphthyl group and a 2-naphthyl group.

As the pyridyl group optionally substituted with X in the definition of W, 2-pyridyl optionally substituted with X
A pyridyl group, a 3-pyridyl group optionally substituted with X or a 4-pyridyl group optionally substituted with X, and preferably a 2-pyridyl group optionally substituted with X or substituted with X Is a 3-pyridyl group which may be substituted, and more preferably a 2-pyridyl group which may be substituted by X.

The thienyl group optionally substituted with X in the definition of W includes 2-optionally substituted thienyl group.
A thienyl group and a 3-thienyl group optionally substituted with X.

-N = CT ⁷ T in the definition of W, R ¹ and Y
⁸ means an alkylideneamino group, a benzylideneamino group, an arylideneamino group or a cycloalkylideneamino group, a methylideneamino group, an ethylideneamino group,
Propylideneamino group, isopropylideneamino group, 4
-Methyl-2-pentylideneamino group, cyclopentylideneamino group, cyclohexylideneamino group and the like.

The C ₁ -C ₄ monoalkylaminosulfonyl groups in the definition of B include methylaminosulfonyl, ethylaminosulfonyl, n-propylaminosulfonyl, isopropylaminosulfonyl and n-
And a butylaminosulfonyl group. Examples of the C ₂ -C ₈ dialkylaminosulfonyl group in the definition of B include a dimethylaminosulfonyl group, a diethylaminosulfonyl group, a di-n-propylaminosulfonyl group, a diisopropylaminosulfonyl group, and a di-n-butylaminosulfonyl group. Can be

The C ₂ -C ₅ monoalkylaminothiocarbonyl group in the definition of B includes methylaminothiocarbonyl group, ethylaminothiocarbonyl group, n-propylaminothiocarbonyl group, isopropylaminothiocarbonyl group and n-butyl And an aminothiocarbonyl group. The C ₃ -C ₉ dialkylaminothiocarbonyl group in the definition of B includes dimethylaminothiocarbonyl group, diethylaminothiocarbonyl group, di-n
-Propylaminothiocarbonyl group, diisopropylaminothiocarbonyl group, di-n-butylaminothiocarbonyl group and the like.

In the definition of B, C ₁ to R ^b substituted with
Examples of the C ₄ alkyl group include a phenacyl group, 2-fluorophenacyl group, 3-chlorophenacyl group, 4-bromophenacyl group, 2-methylphenacyl group, 3-ethylphenacyl group, 4-i-propyl Phenacyl group, 4-t-butylphenacyl group and the like.

In the definition of B, a halogen atom and C
₁ -C ₄ The one or more optionally substituted phenylsulfonyl group selected from an alkyl group, 2-fluorophenyl sulfonyl group, 4-fluorophenyl sulfonyl group, 2-chlorophenyl sulfonyl group, 4-chlorophenyl sulfonyl group A 4-bromophenylsulfonyl group,
2,5-dichlorophenylsulfonyl, pentafluorophenylsulfonyl, 4-methylphenylsulfonyl, 2-methylphenylsulfonyl, 4-t-butylphenylsulfonyl, 2,5-dimethylphenylsulfonyl, 2,4- Dimethylphenylsulfonyl group, 2,4,6-
And a trimethylphenylsulfonyl group, a 2,4,6-tri-i-propylphenylsulfonyl group and the like.

The C ₂ -C ₅ cyanoalkyl group in the definition of B includes a cyanomethyl group, a 2-cyanoethyl group and a 3-cyanoethyl group.
A cyanopropyl group, a 1-cyano-1-methylethyl group and the like.

The C ₃ -C ₉ alkoxycarbonylalkyl group in the definition of B includes a methoxycarbonylmethyl group, an ethoxycarbonylmethyl group, an n-propoxycarbonylmethyl group, an i-propoxy group as a linear or branched alkoxycarbonylalkyl group. Carbonylmethyl group,
n-butoxycarbonylmethyl group, i-butoxycarbonylmethyl group, t-butoxycarbonylmethyl group, n-hexyloxycarbonylmethyl group, n-heptyloxycarbonylmethyl group, 1-methoxycarbonylethyl group, 1-ethoxycarbonylethyl group , 1-n-butoxyethyl group, 2-methoxycarbonylethyl group, 2-ethoxycarbonylethyl group, 1-methoxycarbonylpropyl group, 3-ethoxycarbonylpropyl group, 4-methoxycarbonylbutyl group, 6-
Ethoxycarbonylhexyl group, 1-methoxycarbonyl
Examples thereof include a 1-methylethyl group, a 1-iso-propoxycarbonyl-1-methylethyl group, a 1-ethoxycarbonyl-2-methylpropyl group, and the like.

As the alkali metal in the definition of B,
Lithium, sodium and potassium. As the alkaline earth metal in the definition of B, magnesium,
Calcium, strontium or barium can be mentioned, preferably magnesium, calcium or barium.

NHT in the definition of B^FourT^FiveT⁶Indicated by
Ammonium groups include ammonium Ni-based, monomethyi
Luammonium group, dimethylammonium group, trimethyl
Luammonium group, diethylammonium group, triethyl
Ammonium group, diisopropyl ammonium group,
Isopropylethylammonium group, hexylmethyla
Ammonium group, cyclopropylmethylammonium group,
Cyclohexylmethylammonium group, allylmethyla
Ammonium, benzylmethylammonium or 4
-Methylcyclohexylethylammonium group
Or T^Four, T^FiveAnd T⁶Two of each
Oxygen and nitrogen atoms together with the nitrogen atom to which
Or a 5-membered, 6-membered heterocyclic ring which may contain a sulfur atom
Ring, 7-membered or 8-membered ammonium group, etc.
You.

T ⁴ , T ^{5 in} the definition of T ⁴ , T ⁵ or T ⁶
Heterocyclic 5-, 6-, 7- or 8-membered heterocyclic ring which may contain an oxygen atom, a nitrogen atom or a sulfur atom together with a nitrogen atom to which two of ⁵ and T ⁶ are respectively bonded As the ammonium group, pyrrolidine, pyrazolidine,
Examples include imidazolidine, oxazolidine, isoxazolidine, thiazolidine, piperidine, piperazine, morpholine, thiamorpholine, hexamethyleneimine, and heptamethyleneimine.

The haloalkylsulfenyl group in the definition of G, W, X, Y or Z includes a linear or branched haloalkylthio group such as a fluoromethylthio group, a chlorodifluoromethylthio group, a bromodifluoromethylthio group, Methylthio group, trichloromethylthio group, 2,2,2, -trifluoroethylthio group, 1,
1,2,2-tetrafluoroethylthio group, fluoroethylthio group, pentafluoroethylthio group and fluoro-iso
-Propylthio group and the like.

As the haloalkylsulfinyl group in the definition of G, W, X, Y or Z, straight-chain or branched-chain haloalkylsulfinyl groups such as fluoromethylsulfinyl group, chlorodifluoromethylsulfinyl group, bromodifluoromethylsulfinyl group, Trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2, -trifluoroethylsulfinyl, 1,1,2,2-tetrafluoroethylsulfinyl, fluoroethylsulfinyl, pentafluoroethylsulfinyl and fluoro —Iso-propylsulfinyl group and the like.

As the haloalkylsulfonyl group in the definition of G, W, X, Y or Z, straight-chain or branched-chain haloalkylsulfonyl groups such as fluoromethylsulfonyl group, chlorodifluoromethylsulfonyl group, bromodifluoromethylsulfonyl group, Trifluoromethylsulfonyl group, trichloromethylsulfonyl group, 2,2,
Examples thereof include a 2, -trifluoroethylsulfonyl group, a 1,1,2,2-tetrafluoroethylsulfonyl group, a fluoroethylsulfonyl group, a pentafluoroethylsulfonyl group, and a fluoro-iso-propylsulfonyl group.

The haloalkenyl group in the definition of G or W includes 2-chloroethenyl, 2-bromoethenyl, 2,2-dichloroethenyl and the like as a straight-chain or branched haloalkenyl group having 2 to 4 carbon atoms. can give.

The alkenyloxy group in the definition of G, T ¹ , W or Y includes allyloxy, 2-propenyloxy, 2-butenyloxy, 2-methyl-2- as a linear or branched alkenyloxy group. And a propenyloxy group. As the haloalkenyloxy group in the definition of G, W or Y, a linear or branched haloalkenyloxy group may be a 3-chloro-2-propenyloxy group, a 3,3-dichloro-2-propenyloxy group, A chloro-2-butenyloxy group, a 4,4-dichloro-3-butenyloxy group, a 4,4-difluoro-3-butenyloxy group, and the like.

The alkenylsulfenyl group in the definition of G, W, X, Y or Z includes allylsulfenyl, 2-propenylsulfenyl, 2-butenyls as a linear or branched alkenylsulfenyl group. Examples include a phenyl group and a 2-methyl-2-propenylsulfenyl group. The alkenylsulfinyl group in the definition of G, W, X, Y or Z includes an allylsulfinyl group as a linear or branched alkenylsulfinyl group,
Propenylsulfinyl group, 2-butenylsulfinyl group,
2-methyl-2-propenylsulfinyl group and the like.

The alkenylsulfonyl group in the definition of G, W, X, Y or Z includes allylsulfonyl, 2-propenylsulfonyl, 2-butenylsulfonyl, and 2-methyl- as a straight-chain or branched alkenylsulfonyl group. And a 2-propenylsulfonyl group. G, W
Or as the haloalkenylsulfenyl group in the definition of Y, a 3-chloro-2-propenylsulfenyl group as a linear or branched haloalkenylsulfenyl group, 4
-Chloro-2-butenylsulfenyl group, 3,3-dichloro-2-
Examples include a propenylsulfenyl group, a 4,4-dichloro-3-butenylsulfenyl group, and a 4,4-difluoro-3-butenylsulfenyl group.

As the haloalkenylsulfinyl group in the definition of G, W or Y, a straight-chain or branched haloalkenylsulfinyl group is a 3-chloro-2-propenylsulfinyl group or a 3,3-dichloro-2-propenylsulfinyl group. , 4-chloro-2-butenylsulfinyl group, 4,4-
Dichloro-3-butenylsulfinyl group, 4,4-difluoro-
And a 3-butenylsulfinyl group.

The haloalkenylsulfonyl group in the definition of G, W or Y includes a 3-chloro-2-propenylsulfonyl group and a 3,3-dichloro-2-propenylsulfonyl group as a straight-chain or branched haloalkenylsulfonyl group. , 4-chloro-2-butenylsulfonyl group, 4,4-dichloro-
Examples thereof include a 3-butenylsulfonyl group and a 4,4-difluoro-3-butenylsulfonyl group.

As the haloalkynyl group in the definition of G or W, chloroethynyl, bromoethynyl, iodoethynyl, 3-chloro-1-propynyl, 3-bromo-
And a 1-butynyl group.

The alkynyloxy group in the definition of G, W or Y includes a 2-propynyloxy group, a 2-butynyloxy group, a 1-methyl-2-propynyloxy group and the like. The haloalkynyloxy group in the definition of G, W or Y includes a 3-chloro-2-propynyloxy group,
Examples thereof include a bromo-2-propynyloxy group and a 3-iodo-2-propynyloxy group.

The alkynylsulfenyl group in the definition of G, W or Y includes 2-propynylsulfenyl group, 2-butynylsulfenyl group, 1-methyl-2-propynylsulfenyl group and the like. The alkynylsulfinyl group in the definition of G, W or Y includes 2-propynylsulfinyl group, 2-butynylsulfinyl group, 1-
And a methyl-2-propynylsulfinyl group.

The alkynylsulfonyl group in the definition of G, W or Y includes a 2-propynylsulfonyl group,
Butynylsulfonyl group, 1-methyl-2-propynylsulfonyl group and the like. The haloalkynylsulfenyl group in the definition of G, W or Y includes 3-chloro-2
-Propynylsulfenyl group, 3-bromo-2-propynylsulfenyl group, 3-iodo-2-propynylsulfenyl group and the like.

The haloalkynylsulfinyl group in the definition of G, W or Y includes 3-chloro-2-propynylsulfinyl group, 3-bromo-2-propynylsulfinyl group, 3-iodo-2-propynylsulfinyl group and the like. can give. Examples of the haloalkynylsulfonyl group in the definition of G, W or Y include a 3-chloro-2-propynylsulfonyl group, a 3-bromo-2-propynylsulfonyl group, and a 3-iodo-2-propynylsulfonyl group.

Examples of the alkylcarbonyloxy group in the definition of G, W or Y include an acetoxy group, a propanoyloxy group, a butanoyloxy group, an isopropylcarbonyloxy group and the like. Is done. The benzoyl group which may be substituted by X in the definition of G includes a benzoyl group, a 2-chlorobenzoyl group, a 3-chlorobenzoyl group, a 4-chlorobenzoyl group, a 4-bromobenzoyl group, a 4-fluorobenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, 4-tert-butylbenzoyl group, 3,
4-dichlorobenzoyl group and the like.

The compound of the present invention is useful for so-called agricultural pests that infect agricultural and horticultural crops and trees, so-called livestock pests that infest livestock and poultry, so-called sanitary pests that have various adverse effects on human living environments such as houses, and warehouses. So-called stored pests that injure stored grains and the like, and any pests such as mites, nematodes, mollusks, and crustaceans that occur and injure in similar situations can be effectively controlled at low concentrations.

Insects which can be controlled using the compounds of the present invention;
Specific examples of mites, nematodes, molluscs, and crustaceans include the following, but are not limited thereto. P. serrata, P. serrata, P. serrata, P. serrata, P. serrata, P. japonicus, P. serrata, P. japonicus, P. serrata, P. serrata, P. serrata, P. s. Bowler, fall army worm,
Lepidopteran pests such as codling moths and white-winged starlings, leafhoppers, leafhoppers, brown peach aphids, cotton aphids, cotton aphids, onyx whitefly, tobacco whitefly, pear lice, tsujigumbai, red-spotted beetles, beetles, beetles, etc. Winged pests,
Scarlet beetle, Douganebuuibu, rice water weevil, arimodoki weevil, turtle leaf beetle, cypress flea beetle, colorado beetle, sesame beetle, pine beetle beetle, corn root worm, cocoon elephant, granary weevil, moss Hessian flies, sea flies, medfly, houseflies, flies,
Sheep flies, flies, bullflies, sheep flies, tsetse flies, mosquitoes, Aedes aegypti,
Diptera pests such as Anopheles, Hymenoptera, Pinus sylvestris and Hymenoptera such as Hymenoptera, Thrips palmi, Thrips palmi, Thrips palmi,
Pterodactyl pests such as Thrips thrips and Thrips palmi, Thrips palmi, Thrips japonicus, German cockroaches, etc. Eye pests, cat flea, human flea, isopteryx pests such as mosquito flea, chicken lice, lice lice such as lice, lice, lice such as lice, lice, lice, lice, mites, spider mites, and red spider mites. Spider mites such as red mites, red rust mite, red rust mite, tulip rust mite, red ticks, etc .; , Acarina mites, Acarina mites such as Robin's mite, Dermatophagoid mites such as Honey beetle mites, Dermatophagoid mites such as Oxodid tick, Haemaphysalis longicornis, Dermatophagoides mite such as Dermatophagoid mite, Sweet potato nematode, Kitako Neko nematode, Kitanegusa nematode nematode, Dermatophagoidea nigra Nematodes such as nematodes and pine wood nematodes,
Examples include mollusks such as scallops, slugs, scuttles, and mussels, and crustaceans such as locust beetles.

The plant disease to be controlled by the compound of the present invention includes rice blast (Pyriculari).
a oryzae), Sesame leaf blight (Cochliobo)
rus miyabeanus, Sheath blight (Rhizo)
ctonia solani),

Wheat powdery mildew (Erysiphe)
graminis f. sp. hordei, f. s
p. tritici), leaf spot disease (Pyrenophor)
a graminea), reticulosis (Pyrenophho)
rates), Fusarium head blight (Gibberella)
zeae), rust (Puccinia strii)
formis, P .; Graminis, P .; recon
data, p. hordei), snow rot (Typhul)
a sp. , Micronectriella niv
ais), naked smut (Ustilago tritic)
i, U. nuda), eye spot (Pseudoce)
rcosporella herpotrichoid
es), cloud disease (Rynchosporium se)
calis), leaf blight (Septoria triti)
ci), Fusarium wilt (Leptosphaeria nod)
orum),

Citrus black spot (Diaporthe)
citri), scab (Elsinoe face)
tti), fruit rot (Penicillium di)
gitatum, P .; italicum), Monilia disease of apple (Sclerotinia mali), rot (Valsa mari), powdery mildew (Podo)
sphaera leucotricha), spot leaf spot (Alternaria mali), scab (Ve)
nturia inaequalis, pear scab (Venturia nasicola), black spot (Alternaria Kikuchiana), scab (Gymnosporangium haraea)
num), peach rot (Sclerotinia c)
innerea), scab (Cladosporium)
carpophilum), Phomopsis rot (Ph)
omopsis sp. ),

Grape downy mildew (Plasmopara)
viticola), black rot (Elsinoe am)
pelina), late rot (Glomerella ci)
ngulata), powdery mildew (Uncinula n)
ecator), rust (Phakopsora am)
elopsidis, oyster anthracnose (Gloeos)
porium kaki), deciduous disease (Cercospo)
ra kaki, Mycosphaerella na
wae), downy mildew of cucumber (Pseudopereno)
spora cubensis, anthracnose (Colle)
totrichum lagenarium, powdery mildew (Sphaerotheca fuligine)
a), vine blight (Mycosphaerella me)
lonis), Tomato plague (Phytophthor)
a infestans), ring spot disease (Alternar)
ia solani, leaf mold (Cladospor)
iumfulvam),

Eggplant brown spot disease (Phomopsis ve
xans), powdery mildew (Erysiphe cich)
oracoarum), black spot of cruciferous vegetables (Al
ternaria japonica, vitiligo disease (Ce)
rocosporella brassicae), green onion rust (Puccinia allii), soybean purpura (Cercospora kikuchi)
i), black rot (Elsinoe glycine)
s), black spot disease (Diaporthe phaseolo)
lum), kidney anthracnose (Colletotric)
hum Lindemthianum, Peanut black spot (Mycosphaerella perso)
natum), brown spot (Cercospora ara)
chidicola), pea powdery mildew (Ery)
siphe pisi),

Summer blight of potato (Alternari)
a solani), strawberry powdery mildew (Sphae)
rotheca humuli, tea net blast (E)
xobasidium reticulatum, white scab (Elsinoe leucospila), tobacco scab (Alternaria longipe)
s), powdery mildew (Erysiphe cichola)
ceiling, anthracnose (Colletotrichu)
m tabacum), brown spot of sugar beet (Cerco)
spora beticola, rose scab (Di)
plocarpon rosea), powdery mildew (Sp)
haeothertheca pannosa), brown spot of chrysanthemum (Septoria chrysanthemiin)
dici), white rust (Puccinia horia)
na), Botrytis of various crops
cinerea), sclerotium disease of various crops (Sclero)
(Tinia sclerotiorum) and the like.

That is, the compounds of the present invention can effectively inhibit pests and plant diseases of Orthoptera, Hemiptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, Termites and Lice, at low concentrations. Can be controlled. On the other hand, the compounds of the present invention include extremely useful compounds having almost no adverse effects on mammals, fish, crustaceans and beneficial insects. The compound of the present invention can be synthesized by the following method (Scheme 1). Scheme 1

[0111]

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[Q, A and B in (Scheme 1) have the same meanings as described above, and L is a good leaving group such as a chlorine atom.
A bromine atom, an alkoxy group having 1 to 4 carbon atoms, a phenoxy group, a 1-pyrazolyl group or a 1-imidazolyl group, and L ′ represents a halogen atom, an alkylsulfonyloxy group having 1 to 4 carbon atoms, a benzenesulfonyloxy group, It represents a good leaving group such as a toluenesulfonyloxy group, L ″ represents a halogen atom, alkyl is an alkyl group, preferably an alkyl group having 1 to 4 carbon atoms.] The method A in (Scheme 1) is generally used. By reacting the acetonitrile derivative represented by the formula (3) with an acid chloride or ester represented by the general formula (4) or an acid anhydride represented by the general formula (5), the compound of the present invention (1) The compound (1 ') of the present invention is an alkyl halide, an alkyl sulfonate or a trimethylsilyl halide represented by the general formula (8). Can be converted to the compound (1) of the present invention by reacting the compound with the compound (1) by reacting the compound with the compound (1).
Depending on the type of B in the above, the compound (1 ′) of the present invention is synthesized by reacting dihydropyran, isocyanates or thioisocyanates. By using (4) or (5) in excess in Method A, (1) can also be directly synthesized without isolating (1 ′).

When Q is bonded to an acrylonitrile moiety by a nitrogen atom, it can also be synthesized by Method B. Method B is
A method for synthesizing the compound (1 ′) of the present invention by reacting a heterocyclic ring represented by the general formula (6) with a halogenocyanoketone derivative represented by the general formula (7) will be described. When A is bonded to the acrylonitrile moiety with a nitrogen atom, it can also be synthesized by Method C. Method C refers to a method of synthesizing the compound of the present invention from a cyanoacetic acid derivative represented by the general formula (9) and a heterocyclic compound represented by the general formula (10). The compound represented by the general formula (9) is represented by A
In some cases, it can be synthesized by reacting the acetonitrile derivative represented by the general formula (3) shown by the method with a carbonate in the presence of a base.

In some cases, it is preferable to use a base in the methods described in (Scheme 1) and (Scheme 2). Examples of the base used include alkali metal alkoxides such as sodium ethoxide, sodium methoxide and potassium t-butoxide, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and alkali metal carbonates such as sodium carbonate and potassium carbonate. And organic bases such as triethylamine, pyridine, and DBU; organic lithium compounds such as butyllithium; lithium amides such as lithium diisopropylamine and lithium bistrimethylsilylamide; and sodium hydride.

The reaction shown in (Scheme 1) can be carried out in a solvent inert to the reaction. Examples of the solvent include lower alcohols such as methanol and ethanol; aromatic hydrocarbons such as benzene and toluene; Ethers such as ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, 1,2-diethoxyethane,
Examples include halogenated hydrocarbons such as methylene chloride, chloroform, and 1,2-dichloroethane, amides such as dimethylformamide and dimethylacetamide, acetonitrile, dimethylsulfoxide, and a mixed solvent thereof. In some cases, a mixed solvent of these solvents and water can also be used, and good results may be obtained by adding a quaternary ammonium salt such as tetra-n-butylammonium bromide as a catalyst. Reaction temperature is -3
It is possible to set any temperature between 0 ° C and 200 ° C, and 0 ° C to 150 ° C or 0 ° C when using a solvent.
To the boiling point of the solvent. The base is used in an amount of 0.05 to 10 equivalents, preferably 0.05 to 3 equivalents, of the reaction substrate.

The compound of the present invention can be obtained from the reaction solution by a conventional method. However, when it is necessary to purify the compound of the present invention, it can be separated and purified by any purification method such as recrystallization and column chromatography. Can be. The compounds having an asymmetric carbon among the compounds included in the present invention include optically active compounds (+) and (−).

Compound (3) in (Scheme 1) can be synthesized according to the method described in International Patent Application Publication (WO97 / 40009).

Examples of the compounds included in the present invention are shown in Tables 1 to 4. The abbreviations in the table have the following meanings. Me: methyl group, Et: ethyl group, Pr: propyl group,
Bu: butyl group, Pen: pentyl group, Hex: hexyl group, Hep: heptyl group, Oct: octyl group, No
n: nonyl group, Dec: decyl group, Ph: phenyl group,
n: normal, i: iso, sec: secondary, t: tertiary, c: cyclo,

[0119]

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[0120]

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[0121]

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[0122]

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[0123]

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[0124]

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[0125]

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[Table 1]

[0127]

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[0128]

[Table 1] ──────────────────────────────────── RR ¹ GBY ₁ Y ₂ Y ₃ ── ────────────────────────────────── R1 H 5-Me HHH Me R2 H 5-Cl B1 Me H Et R3 H 2,5-Me ₂ B2 Me Me nPr R4 H 4-Me B3 Me Cl iPr R5 H 2-Me-5-CF ₃ B4 Cl Cl nBu R6 H 4-Ph B5 Cl H iBu R7 HH B6 CF ₃ H sBu R8 H 3-MeO-5-NH ₂ B7 CF ₃ H tBu R9 HH B8 CF ₃ Cl Me R10 H 2-MeS-4-NH ₂ B9 CF ₃ Cl Me R11 HH B10 Cl CF ₃ Me R12 H 5-NO ₂ B11 Cl CF ₃ Me R13 H 4-Br B12 Cl Me Me R14 H 3-nPrO B13 MeO Cl Me R15 HH B14 EtO MeS Me R16 HH B15 CN Cl Me R17 H 1-Me-3,5-Cl ₂ B16 CN NH2 Me R18 H 1,5-Me ₂ B17 NO ₂ Cl Me R19 H 1,3-Me ₂ B18 NO ₂ MeO Me R20 H 1-Me B19 HH Me R21 H 1-Me B20 Me H Me R22 H 5-Ph B21 Me Me Me R23 H 3-Me B22 Me Cl Me ────────────────────────────────────

[0129]

[Table 2] ──────────────────────────────────── RR ¹ GBY ₁ Y ₂ Y ₃ ── ────────────────────────────────── R24 H 5-MeO B24 Cl Cl Me R25 H 5-Ph B25 Cl H Me R26 H 3-Ph B26 CF ₃ H Me R27 H 5-Ph B27 CF ₃ H Me R28 H 4-Me-2-Ph B28 CF ₃ Cl Me R29 HH B29 CF ₃ Cl Me R30 H 5-NH ₂ B30 Cl CF ₃ Me R31 H 1-Me-4-NH ₂ B31 Cl CF ₃ Me R32 HH B32 Cl Me Me R33 HH B33 MeO Cl Me R33 HHH Me Me Me R33 HHH Me Cl Me R33 HHH Cl Cl Me R33 HHH CF ₃ Cl Me R33 HH B6 Me Me Me R33 HH B6 Me Cl Me R33 HH B6 Cl Cl Me R33 HH B6 CF ₃ Cl Me R33 HH B7 Me Me Me R33 HH B7 Me Cl Me R33 HH B7 Cl Cl Me R33 HH B7 CF ₃ Cl Me R33 HH B8 Me Me Me ────────────────────────────────────

[0130]

[Table 3] ──────────────────────────────────── RR ¹ GBY ₁ Y ₂ Y ₃ ── ────────────────────────────────── R33 HH B8 Me Cl Me R33 HH B8 Cl Cl Me R33 HH B8 CF ₃ Cl Me R33 HH B9 Cl Cl Me R33 HH B15 Me Me Me R33 HH B15 Me Cl Me R33 HH B15 Cl Cl Me R33 HH B15 CF ₃ Cl Me R33 HH B16 Me Me Me R33 HH B16 Me Cl Me R33 HH B16 Cl Cl Me R33 HH B16 CF ₃ Cl Me R33 HH B19 Me Me Me R33 HH B19 Me Cl Me R33 HH B19 Cl Cl Me R33 HH B19 CF ₃ Cl Me R33 HH B29 CN NHCOMe Me R34 H 2-Cl B31 NO ₂ Cl Me R35 H 4-Me B34 Me Me Me R35 HH B34 Me Cl Me R35 HH B34 Cl Cl Me R35 HH B34 CF ₃ Cl Me R35 H 4-Me H Me Cl Me ───────────── ───────────────────────

[0131]

[Table 4] ──────────────────────────────────── RR ¹ GBY ₁ Y ₂ Y ₃ ── ────────────────────────────────── R35 H 4-MeO H Cl Cl Me R35 H 4-MeS H CF ₃ Cl Me R35 H 4-CF ₃ H Me Me Me R35 H 4-Cl H Me Cl Me R35 H 4-Me B6 Cl Cl Me R35 H 4-MeO B6 CF ₃ Cl Me R35 H 4-MeS B6 Me Me Me R35 H 4-CF ₃ B7 Me Cl Me R35 H 4-Cl B7 Cl Cl Me R35 H 4-Me B7 CF ₃ Cl Me R35 H 4-MeO B7 Me Cl Me R35 H 4-MeS B8 Cl Cl Me R35 H 4 -CF ₃ B8 CF ₃ Cl Me R35 H 4-Cl B8 Me Me Me R35 H 4-Me B8 Me Cl Me R35 H 4-MeO B15 Cl Cl Me R35 H 4-MeS B15 CF ₃ Cl Me R35 H 4-CF ₃ B15 Me Me Me R35 H 4-Cl B15 Me Cl Me R35 H 4-Me B16 Cl Cl Me R35 H 4-MeO B16 CF ₃ Cl Me R35 H 4-MeS B16 Me Me Me R35 H 4-CF ₃ B16 Me Cl Me ────────────────────────────────────

[0132]

[Table 5] ──────────────────────────────────── RR ¹ GBY ₁ Y ₂ Y ₃ ── ────────────────────────────────── R35 H 4-Cl B17 Cl Cl Me R35 HH B9 CF ₃ Cl Me R36 HHH Me Me Me R36 HHH Me Cl Me R36 HHH Cl Cl Me R36 HHH CF ₃ Cl Me R36 HH B6 Me Me Me R36 HH B6 Me Cl Me R36 HH B6 Cl Cl Me R36 HH B6 CF ₃ Cl Me R36 HH B7 Me Me Me R36 HH B7 Me Cl Me R36 HH B7 Cl Cl Me R36 HH B7 CF ₃ Cl Me R36 HH B8 Me Me Me R36 HH B8 Me Cl Me R36 HH B8 Cl Cl Me R36 HH B8 CF ₃ Cl Me R36 HH B9 Cl Cl Me R36 HH B15 Me Me Me R36 HH B15 Me Cl Me R36 HH B15 Cl Cl Me R36 HH B15 CF ₃ Cl Me ─────────────────────── ─────────────

[0133]

[Table 6] ──────────────────────────────────── RR ¹ GBY ₁ Y ₂ Y ₃ ── ────────────────────────────────── R36 HH B16 Me Me Me R36 HH B16 Me Cl Me R36 HH B16 Cl Cl Me R36 HH B16 CF ₃ Cl Me R36 HH B19 Me Me Me R36 HH B19 Me Cl Me R36 HH B19 Cl Cl Me R36 HH B19 CF ₃ Cl Me R36 HH B29 CN NHCOMe Me R36 HH B31 NO ₂ Cl Me R36 HH B34 Me Me Me R36 HH B34 Me Cl Me R36 HH B34 Cl Cl Me R36 HH B34 CF ₃ Cl Me R36 HH B35 CN NMe ₂ Me R36 HH B36 NO ₂ Cl Me R36 HH B37 Cl Me Me R36 HH B38 MeO Cl Me R36 HH B39 EtO MeS Me R36 HH B40 CN Cl Me R36 HH B41 CN NH2 Me R36 HH B42 NO ₂ Cl Me R36 HH B43 NO ₂ MeO Me ──────────────────── ────────────────

[0134]

[Table 7] ──────────────────────────────────── RR ¹ GBY ₁ Y ₂ Y ₃ ── ────────────────────────────────── R36 HH B44 HH Me R36 HH B45 Me H Me R36 HH B46 Me Me Me R37 H 6-Cl H Me Me Me R38 H 3-Cl H Me Cl Me R39 H 5-Me H Cl Cl Me R40 H 5,6-Me H Me Me Me R41 H 3-Me H Me Cl Me R42 H 6-Me ₂ NH H Cl Cl Me ────────────────────────────────────

[Table 2]

[0136]

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[0137]

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[0138]

[Table 8] RR RR ¹ GBY ₁ Y ₂ Y ₃ ──────────────────────────────────── R1 H 5-Br HH Me Me R2 HH Me ₂ NSO ₂ H Cl Me R3 H 2,5-Me ₂ nHexOCO H Br Et R4 H 2,4-Me ₂ Nicotinoyl Cl Me Me R5 H 2-Me-5-MeCONH Picolinoyl Cl Me nBu R6 H 5-EtO Isonicotinoyl Me H Me R7 H 4-Cl-5-Me H Me MeS Me R8 H 5-Me H Me MeSO Me R9 H 2-Me B1 Me MeSO ₂ Me R10 HH B2 Me NO ₂ Me R11 H 5-MeS nPenCO Me MeCONH Me R12 HH B3 Me Cl Me R13 H 4-NO ₂ B4 Et H Me R14 H 2,5-Cl ₂ B5 Et Cl Me R15 H 2-Me-4-Br B6 nPr Br Me R16 HH B7 CF ₃ Me ₂ C = N Me R17 H 3,5-Cl ₂ -1-Me B8 CN MeS Ph R18 H 5-Me B9 CN Cl Ph R19 H 1-Me B10 Me Me Me R20 H 1-Me B11 Et Me Me R21 H 1-Me- 5-MeNH B12 Me MeO Me R22 H 5-EtS B13 MeO Cl Me R23 H 5-nPr B14 nBuO H Me ───────────────────────── ───────────

[0139]

[Table 9] ──────────────────────────────────── RR ¹ GBY ₁ Y ₂ Y ₃ ──────────────────────────────────── R24 H 3-Br B15 HH Me R25 H 5- Ph B16 Me Et Me R33 H 4,6-Me ₂ B7 Cl Me Me R33 H 4,6- (MeO) ₂ B7 Me Cl Me R33 HHH Cl H Me R33 HHH Me Cl Me R33 HHH Me Me Me R33 HHH Me H Me R33 HH B6 Cl H Me R33 HH B6 Me Cl Me R33 HH B6 Me Me Me R33 HH B6 Me H Me R33 HH B7 Cl H Me R33 HH B7 Me Cl Me R33 HH B7 Me Me Me R33 HH B7 Me H Me R33 HH B8 Cl H Me R33 HH B8 Me Cl Me R33 HH B8 Me Me Me R33 HH B8 Me H Me R33 HH B9 Cl H Me R33 HH B15 Me Cl Me R33 HH B15 Me Me Me ───────── ───────────────────────────

[0140]

[Table 10] ──────────────────────────────────── RR ¹ GBY ₁ Y ₂ Y ₃ ──────────────────────────────────── R33 HH B15 Me H Me R33 HH B15 Cl H Me R33 HH B16 Me Cl Me R33 Cl H B16 Me Me Me R33 Me H B16 Me H Me R33 CO ₂ Me H B16 Cl H Me R33 NO ₂ H B19 Me Cl Me R33 HH B19 Me Me Me R33 HH B19 Me H Me R33 HH B19 Et Cl Me R34 HH B29 Me Cl Me R35 HH B5 Me H Me R35 HH B6 Cl H Me R35 H 4-Me 2-Cl-PhCO Me Cl Me R35 H 4-MeO 3-Cl-PhCO Me Me Me R35 H 4-CF3 4-Cl-PhCO Me H Me R35 H 4-Cl 2,4-Cl ₂ -PhCO Cl H Me R35 HH 2,6-Cl ₂ -PhCO Me Cl Me R35 HH 3,4-Cl _2- PhCO Me Me Me R35 HH B7 Me H Me R35 HH B7 Cl H Me R35 HH B7 Me Cl Me R35 HH B7 Me Me Me ────────────────────── ──────────────

[0141]

[Table 11] ──────────────────────────────────── RR ¹ GBY ₁ Y ₂ Y ₃ ──────────────────────────────────── R35 HH B8 Me H Me R35 HH B8 Cl H Me R35 HH B8 Me Cl Me R35 HHH Et Me Me R35 HHH Me H Me R35 HHH Cl H Me R35 HHH Me Cl Me R36 HHH Me Me Me R36 HHH Me H Me R36 HHH Cl H Me R36 HHH Me Cl Me R36 HH B6 Et Me Me R36 HH B6 Me Me Me R36 HH B6 Me H Me R36 HH B6 Cl H Me R36 HH B7 Me Cl Me R36 HH B7 Et Me Me R36 HH B7 Me Me Me R36 HH B7 Me H Me R36 HH B8 Cl H Me R36 HH B8 Me Cl Me R36 HH B8 Et Me Me R36 HH B8 Me Me Me ──────────────────────────────── ────

[0142]

[Table 12] ──────────────────────────────────── RR ¹ GBY ₁ Y ₂ Y ₃ ──────────────────────────────────── R36 HH B9 Me H Me R36 HH B15 Cl H Me R36 HH B15 Me Cl Me R36 HH B15 Et Me Me R36 HH B15 Me Me Me R36 HH Nicotinoyl Me Me Me R36 HH Picolineoyl Me H Me R36 HH Isonicotinoyl Cl H Me R36 HH B16 Me Cl Me R36 HH B19 Et Me Me R36 HH B19 Me Me Me R36 HH B19 Me H Me R36 HH B19 Cl H Me R36 HH B29 Me Cl Me R36 HH B31 Et Me Me R36 HH B34 Me Me Me R36 HH B34 Me H Me R36 HH B34 Cl H Me R36 HH B34 Me Cl Me R36 HH B35 Et Me Me R36 HH B36 Me Me Me R36 HH B37 Me H Me R36 HH B38 Cl H Me ──────────────────────── ────────────

[0143]

[Table 13] ──────────────────────────────────── RR ¹ GBY ₁ Y ₂ Y ₃ ──────────────────────────────────── R36 HH B39 Me Cl Me R36 HH B40 Et Me Me R36 HH B41 Me Me Me R36 HH B42 Me H Me R36 HH B43 Cl H Me R36 HH B44 Me Cl Me R36 HH B45 Et Me Me R36 HH B46 Me Me Me R37 HHH Me H Me R38 HHH Cl H Me R39 HHH Me Cl Me R40 HHH Et Me Me R41 HHH Me Me Me R42 HHH Me Cl Me ────────────────────────────────── ──

[Table 3]

[0145]

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[0146]

[Table 14] RR ¹ GBY ¹ Y ² ──── ──────────────────────────────── R33 H 4,6-Me ₂ B7 CF ₃ Me R33 H 4,6- (MeO) ₂ B7 Me Me R33 HHH Et Me R33 HHH Me Cl R33 HHH Me NH ₂ R33 HHH Cl Cl R33 HH B6 MeO Me R33 HH B6 MeO Me R33 HH B6 CF ₃ Me R33 HH B6 Me Me R33 HH B7 Me Cl R33 HH B7 Cl Cl R33 HH B7 Me Me R33 HH B7 CF ₃ Me R33 HH B8 Me Cl R33 HH B8 Cl Cl R33 HH B8 Me Me R33 HH B8 CF ₃ Me R33 HH B9 Me Cl R33 HH B15 Me Cl R33 HH B15 Cl Cl R33 HH B15 Me Me R33 HH B15 CF ₃ Me ────────────────────────────────────

[0147]

[Table 15] ──────────────────────────────────── RR ¹ GBY ¹ Y ² ──── ──────────────────────────────── R33 HH B16 Me Cl R33 Cl H B16 Cl Cl R33 Me H B16 Me Me R33 CO ₂ Me H B16 CF ₃ Me R33 NO ₂ H B19 Me Cl R33 HH B19 Cl Cl R33 HH B19 Me Me R33 HH B19 CF ₃ Me R34 HH B29 Me Cl R35 HH B5 Cl Cl R35 HH B6 Me Me R35 H 4- Me 2-Cl-PhCO CF ₃ Me R35 H 4-MeO 3-Cl-PhCO Me Cl R35 H 4-CF3 4-Cl-PhCO Cl Cl R35 H 4-Cl 2,4-Cl ₂ -PhCO Me Me R35 HH 2,6-Cl ₂ -PhCO CF ₃ Me R35 HH 3,4-Cl ₂ -PhCO Me Cl R35 HH B7 Me Cl R35 HH B7 Cl Cl R35 HH B7 Me Me R35 HH B7 CF ₃ Me R35 HH B8 Me Cl R35 HH B8 Cl Cl ────────────────────────────────────

[0148]

[Table 16] ────────────────────────────────────RR ¹ GBY ¹ Y ² ──── ──────────────────────────────── R35 HH B8 Me Me R35 HHH CF ₃ Me R35 HHH Me Cl R35 HHH Cl Cl R35 HHH Me Me R36 HHH Me Cl R36 HHH Cl Cl R36 HHH Me Me R36 HHH CF ₃ Me R36 HH B6 Me Cl R36 HH B6 Cl Cl R36 HH B6 Me Me R36 HH B6 CF ₃ Me R36 HH B7 Me Cl R36 HH B7 Cl Cl R36 HH B7 Me Me R36 HH B7 CF ₃ Me R36 HH B8 Me Cl R36 HH B8 Cl Cl R36 HH B8 Me Me R36 HH B8 CF ₃ Me R36 HH B9 Me Cl R36 HH B15 Cl Cl ────── ──────────────────────────────

[0149]

[Table 17] ──────────────────────────────────── RR ¹ GBY ¹ Y ² ──── ──────────────────────────────── R36 HH B15 Me Me R36 HH B15 CF ₃ Me R36 HH B15 Me Cl R36 HH Nicotinoyl Cl Cl R36 HH Pucorinoyl Me Me R36 HH Isonicotinoyl CF ₃ Me R36 HH B16 Me Me R36 HH B19 Me Cl R36 HH B19 Cl Cl R36 HH B19 Me Me R36 HH B19 CF ₃ Me R36 HH B29 MeO Cl R36 HH B31 Me Me R36 HH B34 Me Cl R36 HH B34 Cl Cl R36 HH B34 Me Me R36 HH B34 CF ₃ Me R36 HH B35 Me Cl R36 HH B36 Cl Cl R36 HH B37 Me Me R36 HH B38 CF ₃ Me R36 HH B39 Me Cl R36 HH B40 Cl Cl ────────────────────────────────────

[0150]

[Table 18] ──────────────────────────────────── RR ¹ GBY ¹ Y ² ──── ──────────────────────────────── R36 HH B41 Me Me R36 HH B42 CF ₃ Me R36 HH B43 Me Cl R36 HH B44 Cl Cl R36 HH B45 Me Me R36 HH B46 CF ₃ Me ────────────────────────────────────

[Table 4]

[0152]

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[0153]

[Table 19] ──────────────────────────────────── RR ¹ GBY ¹ Y ² ──── ──────────────────────────────── R33 H 4,6-Me ₂ HHH R33 H 4,6- (MeO) ₂ HFH R33 HHH Cl H R33 HHH Br H R33 HHH Me H R33 HHH Me Me R33 HHH NH ₂ H R33 HHH NHCOMe H R33 HHH CN H R33 HHH OH H R33 HHH MeO H R33 HHH EtO H R33 HHH nPrO H R33 HHH CHF ₂ OH R33 HHH CBrF ₂ OH R33 HHH CF ₃ OM R33 HHH MeS H R33 HHH MeSO H R33 HHH MeSO ₂ H R33 HHH SH H R33 HHH EtS H R33 HHH iBuS H R33 HHH EtS H ───────── ───────────────────────────

[0154]

[Table 20] ──────────────────────────────────── RR ¹ GBY ¹ Y ² ──── ──────────────────────────────── R33 HHH iBuS H R33 Cl HH CH ₂ = CHCH ₂ SH R33 Me HH CH ₂ = CHCH ₂ SO M R33 CO ₂ Me HH CH ₂ = CHCH ₂ SO ₂ H R33 NO ₂ HH MeCH = CHCH ₂ SH R33 HHH CH ₂ = C (Me) CH ₂ SH R33 HHH CH≡CC H ₂ SH R33 HHH CH ≡CC H ₂ SO H R33 H 4,6-Me ₂ B7 HH R33 H 4,6- (MeO) ₂ B7 FH R33 HH B7 Cl H R33 HH B7 Br H R33 HH B7 Me H R33 HH B7 Me Me R33 HH B7 NH ₂ H R33 HH B7 NHCOMe H R33 HH B7 CN H R33 HH B7 OH H R33 HH B7 MeO H R33 HH B7 EtO H R33 HH B7 nPrO H R33 HH B7 CHF ₂ OH R33 HH B7 CBrF ₂ OH ────────────────────────────────

[0155]

[Table 21] ──────────────────────────────────── RR ¹ GBY ¹ Y ² ──── ──────────────────────────────── R33 HH B7 CF ₃ OM R33 HH B7 MeS H R33 HH B7 MeSO H R33 HH B7 MeSO ₂ H R33 HH B7 SH H R33 HH B7 EtS H R33 HH B7 iBuS H R33 HH B7 EtS H R33 HH B6 iBuS H R33 Cl H B6 Cl H R33 Me H B6 Me H R33 CO ₂ Me H B6 MeO H R33 NO ₂ H B6 MeS H R33 HH B8 Cl H R33 HH B8 Me H R33 HH B8 Me H R34 HHH CH≡CC H ₂ SO ₂ H R35 HHH CF ₃ SH R35 HHH CF ₃ SO H R35 H 4-Me H CF ₃ SO ₂ H R35 H 4-MeO H Cl ₂ C = CHCH ₂ SH R35 H 4-CF3 H Cl ₂ C = CHCH ₂ SO H R35 H 4-Cl H Cl ₂ C = CHCH ₂ SO ₂ H ───── ───────────────────────────────

[0156]

[Table 22] ──────────────────────────────────── RR ¹ GBY ¹ Y ² ──── ──────────────────────────────── R35 HHH CF ₃ CH ₂ OH R35 HHHH Me R35 HHHH CF ₃ R35 HHHH CO ₂ Me R35 HHHH MeO R35 HHHH NH2 R35 HHH Me CF ₃ R35 HHHH OH R36 HHHHH R36 HHHFH R36 HHH Cl H R36 HHH Br H R36 HHH Me H R36 HHH Me Me R36 HHH NH ₂ H R36 HHH NHCOMH H R36 HH CN OH H R36 HHH MeO H R36 HHH EtO H R36 HHH nPrO H R36 HHH CHF ₂ OH R36 HHH CBrF ₂ OH ──────────

[0157]

[Table 23] RR ¹ GBY ¹ Y ² ──── ──────────────────────────────── R36 HHH CF ₃ OH R36 HHH Cl H R36 HHH Me H R36 HH B5 Cl H R36 HH B5 Me H R36 HH B6 Cl H R36 HH B6 Me H R36 HH B7 Cl H R36 HH B7 Me H R36 HH B8 Cl H R36 HH B8 Me H R36 HH B9 Cl H R36 HH B9 Me H R36 HH B15 Cl H R36 HH B19 Me H R36 HH B19 Cl H R36 HH B22 Me H R36 HH B22 Cl H R36 HH B34 Me H R36 HH B34 Cl H R36 HH B35 Me H R36 HH B35 Cl H R36 HH B36 Me H ───── ───────────────────────────────

[0158]

[Table 24] RR ¹ GBY ¹ Y ² ──── ──────────────────────────────── R36 HH B36 Cl H R36 HH B37 Me H R36 HH 2-Cl-PhCO Cl H R36 HH 3-Cl-PhCO Me H R36 HH 4-Cl-PhCO Cl H R36 HH 2,4-Cl ₂ -PhCO Me H R36 HH 2,6-Cl ₂ -PhCO Cl H R36 HH 2-F-PhCO Me H R36 HH 2,6-F-PhCO Cl H ────────────────────────────────────

In applying the compound of the present invention, it is usually mixed with an appropriate solid carrier or liquid carrier, and if necessary, a surfactant, a penetrant, a spreading agent, a thickener, a deicing agent,
A binder, an anti-caking agent, a disintegrating agent, an anti-decomposition agent, etc. are added, and the solution, emulsion, wettable powder, aqueous solvent, wettable powder for granules, aqueous solvent for granules, suspension, emulsion, suspo It can be put to practical use in preparations of any dosage form such as emulsions, microemulsions, powders, granules and gels. Further, from the viewpoint of labor saving and improvement of safety, the above-mentioned preparation of any dosage form can be provided by being enclosed in a water-soluble package.

Examples of the solid carrier include natural minerals such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite and diatomaceous earth, calcium carbonate, ammonium sulfate, sodium sulfate and potassium chloride. And the like, synthetic silicic acid and synthetic silicate. As liquid carriers, for example, 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; 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. As a surfactant,
Nonionic properties such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, and polyoxyethylene sorbitan fatty acid ester Surfactant, alkyl sulfate, alkyl benzene sulfonate, lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonate, alkyl naphthalene sulfonate, salt of naphthalene sulfonic acid formalin condensate, alkyl naphthalene sulfonic acid formalin Salts of condensates, polyoxyethylene alkylaryl ether sulfates and phosphates, polyoxyethylene styryl phenylate Anionic surfactants such as sulfuric acid and phosphates, polycarboxylates and polystyrene sulfonates, cationic surfactants such as alkylamine salts and alkylquaternary ammonium salts, and amphoteric surfactants such as amino acid type and betaine type Is mentioned.

The content of these surfactants is not particularly limited, but is preferably in the range of usually 0.05 to 20 parts by weight based on 100 parts by weight of the preparation of the present invention. These surfactants may be used alone or in combination of two or more. When the compound of the present invention is used as a pesticide, other types of herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, plant growth regulators and the like may be used as needed during formulation or spraying. You may mix and apply with a power agent, a fertilizer, a soil conditioner, etc.

In particular, by applying a mixture with other agricultural chemicals or plant hormones, it is expected that the cost can be reduced by reducing the amount of the applied medicine, the insecticidal spectrum can be expanded by the synergistic action of the mixed medicine, and a higher pest control effect can be expected. On this occasion,
A combination with a plurality of known pesticides is also possible at the same time. Examples of the kind of pesticide to be used in combination with the compound of the present invention include, for example, Farm Chemicals Handbook (Farm
Chemicals Handbook), 1994, and the like.

The applied amount of the compound of the present invention varies depending on the application scene, application time, application method, cultivated crops, etc., but is generally 0.000 per hectare (ha) as an active ingredient.
About 5 to 50 kg is appropriate. Next, a formulation example of a preparation when the compound of the present invention is used is specifically shown. However, the composition examples of the present invention are not limited to these. In the following formulation examples, "parts" means parts 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 Others include, for example, an anti-caking agent and a decomposition inhibitor. .

[Emulsion] 0.1 to 30 parts of the compound of the present invention 45 to 95 parts of a liquid carrier Surfactant 4.9 to 15 parts Others 0 to 10 parts Others include, for example, a spreading agent and a decomposition inhibitor.

[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 Others include, for example, an antifreezing agent and a thickener.

[Water dispersible granule] 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 Others include, for example, a binder and a decomposition inhibitor.

[Solution] Compound of the present invention 0.01 to 70 parts Liquid carrier 20 to 99.99 parts Others 0 to 10 parts Others include, for example, an antifreezing agent and a spreading agent.

[Granules] Compound of the present invention 0.01 to 80 parts Solid carrier 10 to 99.99 parts Others 0 to 10 parts Others include, for example, 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 Others include, for example, a drift inhibitor, a decomposition inhibitor and the like.

[0172]

EXAMPLES The synthesis examples, preparation examples, and test examples of the compound of the present invention are specifically described below as examples, but the present invention is not limited to these examples. Synthesis Example 1 Synthesis of 3- (4-chloro-1,3-dimethylpyrazol-5-yl) -3-hydroxy-2- (2-pyrazinylthiazol-4-yl) acrylonitrile (Compound No. 1) ).

2.00 g of 4-cyanomethyl-2-pyrazinylthiazole and 4-chloro-1,3-dimethyl-5
2.44 g of-(1-pyrazolylcarbonyl) pyrazole
Was added to 50 ml of dry tetrahydrofuran, and 2.22 g of potassium t-butoxide was added under ice-cooling and stirring. After stirring for 30 minutes under ice cooling, 50 ml of ice water was added and neutralized with 1N hydrochloric acid. After extraction with 1-butanol (50 ml), the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product. This was washed with isopropyl ether and dried to obtain 1.90 g of the target compound. Melting point: 228.5-230.0 ° C The following compounds were synthesized in the same manner.

3- (2-chloro-4-methylthiazol-5-yl) -3-hydroxy-2- (2-pyrazinylthiazol-4-yl) acrylonitrile (compound N
o. 2, melting point: 214-215 ° C)

3- (2-chloropyridin-3-yl)-
3-hydroxy-2- (2-pyrazinylthiazole-4
-Yl) acrylonitrile (Compound No. 3, melting point: 2)
73-274.5 ° C)

3- (5-Chloro-1-methyl-3-trifluoromethylpyrazol-4-yl) -3-hydroxy-2- (2-pyrazinylthiazol-4-yl) acrylonitrile (Compound No. 4) , Melting point: 230-231
℃)

3- (4-Chloro-1,3-dimethylpyrazole) -3-hydroxy-2- (2-pyrazinylthiazol-4-yl) acrylonitrile (Compound No.
5, melting point: 294-296 ° C)

2- {4- (5-Chloro-1-methylpyrazol-4-yl) thiazol-2-yl} -3- (5
-Chloro-1-methyl-3-trifluoromethylpyrazol-4-yl) -3-hydroxyacrylonitrile (Compound No. 6, melting point: 238-243 ° C)

3- (4-Chloro-1,3-dimethylpyrazol-5-yl) -2- {3- (2,4-dimethylthiazol-5-yl) pyrazol-1-yl} -2-
(3-hydroxyacrylonitrile (Compound No. 7,
¹ H-NMR (ppm) (CDCl ₃ ) 2.28 (s, 3H), 2.60 (s, 3H), 2.69 (s, 3
H), 2.94 (s, 3H), 6.61 (d, J = 3Hz, H), 7.79 (d, J = 3Hz, H))

3- (4-Chloro-1,3-dimethylpyrazol-5-yl) -2- {3- (furan-2-yl)
Pyrazol-1-yl} -3-hydroxyacrylonitrile (Compound No. 8, ¹ H-NMR (ppm) [CDCl ₃ ] 2.25 (s, 3
H), 3.91 (s, 3H), 6.38-6.53 (m, H), 6.49-6.83 (m, H), 6.70
(d, J = 3Hz, H), 7.41-7.81 (m, H), 7.85 (d, J = 3Hz, H))

3- (4-chloro-1,3-dimethylpyrazol-5-yl) -2- {3- (5-methylfuran-
2-yl) pyrazol-1-yl} -2- (3-hydroxyacrylonitrile (Compound No. 9, ¹ H-NMR (ppm)
[CDCl _3] 2.25 (s, 3H), 2.33 (s, 3H), 3.92 (s, 3H), 6.05 (br
d, J = 3Hz, H), 6.62 (d, J = 3Hz, H), 6.62 (d, J = 3Hz, H), 7.52 (d,
J = 3Hz, H))

[Synthesis Example 2] 3- (4-Chloro-1,3-
Synthesis of dimethylpyrazol-5-yl) -3-pivaloyloxy-2- (2-pyrazinylthiazol-4-yl) acrylonitrile (Compound No. 10). 0.1 g of 60% sodium hydride was washed with n-hexane, and 20 ml of dry tetrahydrofuran was added. Under ice-cooled stirring 3-
After slowly adding 0.60 g of (4-chloro-1,3-dimethylpyrazole) -3-hydroxy-2- (2-pyrazinylthiazol-4-yl) acrylonitrile,
Stirred at room temperature for 1 hour. Pivaloyl chloride 0.25
g was added dropwise, and the mixture was further stirred for 6 hours. The reaction solution was poured into ice water and extracted with 50 ml of ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product. This was washed with isopropyl ether to obtain 0.49 g of the desired compound. Melting point: 178-179 ° C The following compounds were synthesized in the same manner.

3- (2-chloro-4-methylthiazol-5-yl) -3-pivaloyloxy-2- (2-pyrazinylthiazol-4-yl) acrylonitrile (Compound No. 11, E-form / Z-form) Mixture, 87 / HPLC
6, melting point 145-150 ° C)

3- (4-Chloro-1,3-dimethylpyrazol-5-yl) -2- {3- (2,4-dimethylthiazol-5-yl) pyrazol-1-yl} -2-
(3-pivaloyloxyacrylonitrile (compound N
o. 12, ¹ H-NMR (ppm) [CDCl ₃ ] 1.22 (s, 9H), 2.27 (s, 3
H), 2.61 (s, 3H), 2.70 (s, 3H), 4.00 (s, 3H), 6.66 (d, J = 3Hz,
H), 7.87 (d, J = 3Hz, H))

3- (4-Chloro-1,3-dimethylpyrazol-5-yl) -2- {3- (furan-2-yl)
Pyrazol-1-yl} -3-pivaloyloxyacrylonitrile (Compound No. 13, ¹ H-NMR (ppm) [CDCl ₃ ]
1.24 (s, 9H), 2.27 (s, 3H), 3.98 (s, 3H), 6.40-6.59 (m, H), 6.
68-6.83 (m, H), 6.75 (d, J = 3Hz, H), 7.43-7.55 (m, H), 7.83
(d, J = 3Hz, H))

3- (4-Chloro-1,3-dimethylpyrazol-5-yl) -2- {3- (5-methylfuran-
2-yl) pyrazol-1-yl} -2- (3-pivaloyloxyacrylonitrile (Compound No. 14, ¹ HN
MR (ppm) (CDCl ₃ ) 1.24 (s, 9H), 2.26 (s, 3H), 2.37 (s, 3H),
3.98 (s, 3H), 6.05 (brd, J = 3Hz, H), 6.63 (d, J = 3Hz, H), 6.63
(d, J = 3Hz, H), 7.78 (d, J = 3Hz, H))

[Formulation Examples] Next, formulation examples of pest control agents containing the compound of the present invention as an active ingredient are shown, but the present invention is not limited to these. In the following formulation examples,
"Parts" means parts by weight.

[Formulation Example 1] Water-dispersible compound of the present compound No. 1 1 25 parts Pyrophyllite 71 parts Solpol 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 The above is uniformly mixed and pulverized into a wettable powder.

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

[Formulation Example 3] Suspending agent (flowable agent) 125 parts Agrisol S-710 10 parts (Nonionic surfactant: Kao Corporation trade name) Lunox 1000C 0.5 parts (Anionic surfactant: Toho Chemical Industry Co., Ltd.) Xanthan gum 0.2 Part Water 64.3 parts After uniformly mixing the above, wet pulverization is performed to obtain a suspending agent.

[Formulation Example 4] Water dispersible granule (dry flowable) 1 75 parts Hytenol NE-15 5 parts (anionic surfactant: Daiichi Kogyo Pharmaceutical Co., Ltd.) Vanirex N 10 parts (anionic surfactant: Nippon Paper Industries Co., Ltd.) Carplex # 80D 10 parts (synthetic hydrous silicic acid: Shionogi Pharmaceutical Co., Ltd.) After uniformly mixing and pulverizing the above, adding a small amount of water, stirring and mixing and kneading, granulating with an extrusion granulator, and drying. Granular wettable powder.

[Compounding Example 5] Granules Compound of the present invention 15 parts Bentonite 50 parts Talc 45 parts After uniformly mixing and pulverizing the above, a small amount of water is added, and the mixture is kneaded with stirring, granulated by an extrusion granulator, and dried to obtain granules.

[Formulation Example 6] Powder Compound No. 13 parts Carplex # 80D 0.5 part (Synthetic hydrated silica: trade name of Shionogi & Co., Ltd.) Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above components are uniformly mixed and pulverized to obtain a powder.

For use, the above-mentioned wettable powder, emulsion, flowable and granular wettable powder are diluted 50 to 20,000 times with water to give an active ingredient of 0.005 to 0.005 per hectare (ha).
Spray to 50kg.

[Test Examples] The usefulness of the compound of the present invention as a pesticidal agent will be specifically described in the following test examples.

Test Example 1 Insecticidal Test Against Brown Planthopper A 5% emulsion of the compound of the present invention described in the specification (25% wettable powder was used depending on the compound) was diluted with water containing a spreading agent to give a concentration of 500 ppm. Was prepared. This chemical was sprayed in a sufficient amount on the foliage of rice planted in a 1/2000 are pot. After air-drying, the cylinder was erected and 10 larvae of the second instar larva of brown planthopper were released per pot, capped and stored in a thermostat. The survey was conducted after 6 days, and the mortality was calculated from the following formula. The test was performed in two sections.

Mortality (%) = [Number of dead insects / (Number of dead insects + Number of surviving insects)] × 100 As a result, the following compounds showed a mortality of 80% or more. The compound of the present invention no. : 1,2,10,11,13

Test Example 2 Insecticidal Test Against Leafhopper Leafhopper The foliage of rice was immersed in an emulsion of the compound of the present invention at a concentration of 500 ppm for about 10 seconds, and the foliage was placed in a glass cylinder to show resistance to the organophosphorus insecticide. Release the adults, cover them with perforated lids and store them in a thermostat at 25 ° C.
The number of dead insects after the day was investigated, and the mortality was determined from the same formula as in Test Example 1. Note that the test was performed in a two-section system. As a result, the following compounds showed a mortality of 80% or more.

The compound of the present invention no. : 1, 2, 10, 1
1, 13, 14

Test Example 3 Insecticidal test against peach aphid Moist filter paper was spread on a glass petri dish having an inner diameter of 3 cm, and cabbage leaves having the same diameter were placed thereon. Four wingless adult female peach aphids were released, and one day later, a chemical solution was sprayed (2.5 mg / cm 2) using a rotary spray tower. The drug solution was prepared by diluting a 5% emulsion of the compound of the present invention described in the specification (25% wettable powder was used depending on the compound) with water containing a spreading agent.
The one adjusted to a concentration of 00 ppm was used. Six days after the treatment, adult and larval mortality was determined from the following formula. The test was performed in two sections.

Mortality (%) = [Number of dead insects / (Number of dead insects + Number of surviving insects)] × 100 As a result, the following compounds showed a mortality of 80%. The compound of the present invention no. : 1, 2, 7, 8, 9, 10, 1
1, 12, 13, 14

Test Example 4 Contact Insecticidal Test on P. conch The perilla leaves were immersed for about 10 seconds in an aqueous emulsion of the compound of the present invention at a concentration of 500 ppm, air-dried and placed in a petri dish. Ten animals were released, each was covered with a perforated lid, housed in a thermostat at 25 ° C., the number of dead insects after 6 days was investigated, and the mortality was calculated from the same formula as in Test Example 1. Note that the test was performed in a two-section system. As a result, the following compounds showed a mortality of 80% or more.

The compound of the present invention No. : 1,2,8,10,11

Test Example 5 Insecticidal Test Against Spiny Beetle A 5% emulsion of the compound of the present invention described in the specification (a 25% wettable powder was used depending on the compound) was diluted with water containing a spreading agent to give 500 ppm. The cucumber leaf was immersed in this solution for about 10 seconds, air-dried and placed in a petri dish, into which the second instar larvae of cucumber beetle were placed at a rate of 1 per petri dish.
Zero insects were released, covered and housed in a constant temperature room at 25 ° C., and the mortality after 6 days was determined from the same formula as in Test Example 1.
The test was performed in two sections.

As a result, the following compounds showed 100% mortality. The compound of the present invention no. 1, 2, 10, 11

Test Example 6 Test of Acaricidal Activity against Spider Mite A kidney bean was cut into a circle having a diameter of 3.0 cm using a leaf punch and placed on a wet filter paper on a styrene cup having a diameter of 7 cm. In addition, one spider mite larva per leaf
0 animals were inoculated. 5% of the compound of the invention described in the description
The emulsion (25% wettable powder is used depending on the compound) is diluted with water containing a spreading agent to adjust to a chemical solution having a concentration of 500 ppm, and the chemical solution is sprayed using a rotary spray tower at a rate of 2 ml per styrene cup. And housed in a constant temperature room at 25 ° C.
The mortality after the lapse of time was determined from the same formula as in Test Example 1. The test was performed in two sections. As a result, the following compounds showed a mortality of 80% or more.

The compound of the present invention No. : 1, 7, 8, 9, 1
1, 12, 13, 14

[0208]

As a result of the long-term use of insecticides and fungicides, pests have recently become resistant, making it difficult to control them with conventional insecticides and fungicides. Some insecticides are highly toxic, and some are persisting in ecosystems due to persistence. Therefore, the present invention provides a novel insecticide or fungicide having low toxicity and low residual, and also provides an underwater biofouling inhibitor with little effect on ecosystems and secondary pollution.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁶ Identification code FI A01N 43/78 A01N 43/78 B 43/824 C07D 401/14 231 43/828 417/06 231 43/836 417/14 213 C07D 401/14 231 231 417/06 231 A01N 43/82 101 417/14 213 102 231 104 (72) Inventor Yoshihide Masuzawa 722-1, Tsuboi-cho, Funabashi-shi, Chiba Pref. Nissan Chemical Industry Co., Ltd. Central Research Laboratory (72) Inventor Toshiro Miyake 1470, Shirooka, Shirooka-cho, Minami-Saitama-gun, Saitama Prefecture Nissan Chemical Industry Co., Ltd.Bioscience Research Institute (72) Inventor Yoichi Inoue 1470, Shirooka-machi, Shiraoka-cho, Minami-Saitama-gun, Saitama Prefecture Nissan Chemical Industry Co., Ltd. Inventor Norihiko Mimori 1470 Shirooka, Shiraoka-cho, Minamisaitama-gun, Saitama Prefecture Nissan Chemical Industry Co., Ltd. Inventor Takii new self Saitama Prefecture Minami-Saitama District Shiraoka-cho Oaza Shiraoka 1470 Nissan Chemical Industry Co., Ltd. Biological Sciences in the Institute

Claims (5)

[Claims] (1) Formula (1):Wherein Q is R and (R¹) A thiazolyl group substituted with n,
Or R and (R¹A) a pyrazolyl group substituted with n
A represents phenyl optionally substituted with W, substituted with W
May be substituted by naphthyl or Y
Heterocyclic groups (provided that the heterocyclic groups are thienyl,
, Pyrrolyl, oxazolyl, isoxazolyl, thiazo
Ryl, isothiazolyl, pyrazolyl, imidazolyl,
1,3,4-oxadiazolyl, 1,2,4-oxadi
Azolyl, 1,3,4-thiadiazolyl, 1,2,4-
Thiadiazolyl, 1,2,4-triazolyl, 1,2,2
3-thiadiazolyl, 1,2,3-triazolyl, 1,
2,3,4-tetrazolyl, pyridinyl, pyrimidiny
, Pyrazinyl, pyridazinyl, 1,3,5-triazi
Nil, 1,2,4-triazinyl, indazolyl, ben
Zoxazolyl, quinolinyl, isoquinolinyl, quinoki
Salinyl, phthalazinyl, cinnolinyl or quinazoly
Nil. B is H, C₁~ C_FourAlkyl, C₁~ C_FourHaloalkyl,
C_Two~ C_FourAlkoxyalkyl, CH_ThreeSCH_Two, CH_ThreeO
C_TwoH_FourOCH_Two, R^aC substituted with₁~ C_FourAlkyl, R
^bC substituted with₁~ C_FourAlkyl, tetrahydropyrani
Le, (CH_Three)_ThreeSi, C₁~ C_FourAlkylsulfonyl, ha
Logen or C₁~ C_FourMay be substituted with alkyl
Phenylsulfonyl, -SO_TwoCF_Three, C₁~ C_FourMonoa
Alkylaminosulfonyl, C_Two~ C₈Dialkylaminos
Ruphonyl, phenylaminosulfonyl, C_Two~ C_FiveMonoa
Alkylaminothiocarbonyl, C_Three~ C₉Dialkylamid
Nothiocarbonyl, C_Two~ C_FiveCyanoalkyl, C_Three~ C₉
Alkoxycarbonylalkyl, -C (= O) T¹, −
P (= O) T^TwoT^Three, -P (= S) T^TwoT^Three, Alkali metal
Atom, alkaline earth metal atom or NHT^FourT^FiveT⁶In
R is a heterocyclic group optionally substituted by G (provided that
Heterocyclic groups are furyl, pyrrolyl, oxazolyl, isoxa
Zolyl, thiazolyl, isothiazolyl, pyrazolyl, i
Midazolyl, 1,3,4-oxadiazolyl, 1,2,2
4-oxadiazolyl, 1,3,4-thiadiazolyl,
1,2,4-thiadiazolyl, 1,2,4-triazolyl
1,2,3-thiadiazolyl, 1,2,3-tria
Zolyl, 1,2,3,4-tetrazolyl, pyrimidini
, Pyrazinyl, pyridazinyl, 1,3,5-triazi
Nil, 1,2,4-triazinyl, benzothiazolyl,
Benzimidazolyl, indazolyl, benzoxazoly
Quinolinyl, isoquinolinyl, quinoxalinyl,
Tarazinyl, cinnolinyl or quinazolinyl
You. ) And R¹Is halogen, C₁~ C_FiveAlkoxycarbonyl, N
O_Two, CN, -NU¹U^TwoOr -N = CT⁷T⁸N is an integer of 0 or 1, W is halogen, C₁~ C_TenAlkyl, R^aReplaced by
C₁~ C_FourAlkyl, C _Two~ C₆Alkenyl, C_Two~ C₆A
Lucinyl, C₁~ C₆Haloalkyl, C_Two~ C₆Halo arche
Nil, C_Two~ C₆Haloalkynyl, C_Three~ C₆Halocycloa
Luquil, C₁~ C_ThreeC optionally substituted with alkyl_Three
~ C₆Cycloalkyl, C₁~ C₆Alkoxy, C_Two~ C₆
Alkenyloxy, C_Two~ C₆Alkynyloxy, C₁~
C_FourHaloalkoxy, C_Two~ C₆Haloalkenyloxy,
C_Two~ C₆Haloalkynyloxy, C ₁~ C_FourAlkylsul
Phenyl, C₁~ C_FourAlkylsulfinyl, C₁~ C_FourA
Rukylsulfonyl, C_Two~ C₆Alkenylsulfenyl,
C_Two~ C₆Alkenylsulfinyl, C_Two~ C₆Alkenyl
Sulfonyl, C_Two~ C₆Alkynylsulfenyl, C_Two~
C₆Alkynylsulfinyl, C_Two~ C₆Alkynyls
Ruphonyl, C₁~ C_FourHaloalkylsulfenyl, C₁~
C_FourHaloalkylsulfinyl, C₁~ C_FourHaloalkyl
Sulfonyl, C_Two~ C₆Haloalkenylsulfenyl, C
_Two~ C₆Haloalkenylsulfinyl, C_Two~ C₆Haloal
Kenylsulfonyl, C_Two~ C₆Haloalkynylsulfeni
Le, C_Two~ C₆Haloalkynylsulfinyl, C_Two~ C₆C
Loalkynylsulfonyl, NO_Two, CN, -NU¹U^Two,
Phenoxy, OH, naphthyl, C_Two~ C₇Alkoxycal
Bonil, C_Two~ C_FourAlkoxyalkyl, C_Two~ C_FourArchi
Lecarbonyl, C_Two~ C_FiveAlkylcarbonyloxy, C
_Two~ C_FiveHaloalkylcarbonyloxy, substituted with X
Benzoyl, optionally substituted with X
Nil, pyridyl optionally substituted by X, substituted by X
Optionally thienyl and -N = CT⁷T⁸From within
1 to 4 substituents arbitrarily selected, or adjacent
5 formed by an alkylene group bonded at the substitution position
Or an 8-membered ring, Y is halogen, C₁~ C_TenAlkyl, C₁~ C₆Haloa
Luquil, C₁~ C₆Alkoxy, C_Two~ C₆Alkenyloxy
Si, C_Two~ C₆Alkynyloxy, C₁~ C_FourHaloalkoki
Si, C_Two~ C₆Haloalkenyloxy, C_Two~ C₆Haloal
Quinyloxy, C₁~ C_FourAlkylsulfenyl, C₁~
C_FourAlkylsulfinyl, C₁~ C_FourAlkylsulfoni
Le, C_Two~ C₆Alkenylsulfenyl, C_Two~ C₆Arche
Nilsulfinyl, C_Two~ C₆Alkenylsulfonyl, C
_Two~ C₆Alkynylsulfenyl, C _Two~ C₆Alkynyls
Rufinil, C_Two~ C₆Alkynylsulfonyl, C₁~ C_Four
Haloalkylsulfenyl, C₁~ C_FourHaloalkylsul
Finil, C₁~ C_FourHaloalkylsulfonyl, C_Two~ C₆
Haloalkenylsulfenyl, C_Two~ C₆Haloalkenyl
Sulfinyl, C_Two~ C₆Haloalkenylsulfonyl, C
_Two~ C₆Haloalkynylsulfenyl, C_Two~ C₆Haloal
Quinylsulfinyl, C_Two~ C₆Haloalkynylsulfoni
Le, NO_Two, CN, -NU¹U^Two, OH, C_Two~ C₇Arco
Xycarbonyl, C_Two~ C_FourAlkoxyalkyl, C_Two~
C_FiveAlkylcarbonyloxy, C_Two~ C_FiveHaloalkyl
Carbonyloxy, C_Three~ C₇Dialkylaminocarboni
Ruoxy, phenyl optionally substituted with X, and
-N = CT⁷T⁸(However, T⁷And T⁸Are each independently H,
Phenyl, benzyl or C₁~ C₆Is alkyl,
T⁷And T⁸5 to 8 members together with the carbon atom to which
A ring may be formed. 1) is not arbitrarily selected from
Or four substituents, or
A 5- to 8-membered ring formed by a alkylene group;₁~ C₆Alkyl, C₁~ C_FourHaloal
Kill, C₁~ C_FourAlkoxy, C₁~ C_FourHaloalkoxy,
C₁~ C_FourAlkylsulfenyl, C₁~ C_FourAlkylsul
Finil, C₁~ C_FourAlkylsulfonyl, C₁~ C_FourHalo
Alkylsulfenyl, C₁~ C_FourHaloalkyl sulfy
Nil, C₁~ C_FourHaloalkylsulfonyl, C_Two~ C_FourAl
Kenil, C_Two~ C_FourHaloalkenyl, C_Two~ C_FourAlkenyl
Oxy, C_Two~ C_FourHaloalkenyloxy, C_Two~ C_FourAl
Kenylsulfenyl, C_Two~ C_FourAlkenylsulfini
Le, C_Two~ C_FourAlkenylsulfonyl, C_Two~ C_FourHaloal
Kenylsulfenyl, C_Two~ C_FourHaloalkenyl sulphie
Nil, C_Two~ C_FourHaloalkenylsulfonyl, C_Two~ C_FourA
Lucinyl, C_Two~ C_FourHaloalkynyl, C_Two~ C_FourAlkini
Luoxy, C_Two~ C_FourHaloalkynyloxy, C_Two~ C_FourA
Ruquinylsulfenyl, C_Two~ C_FourAlkynyl sulfini
Le, C_Two~ C_FourAlkynylsulfonyl, C_Two~ C_FourHaloal
Quinylsulfenyl, C_Two~ C_FourHaloalkynyl sulfy
Nil, C_Two~ C_FourHaloalkynylsulfonyl, NO_Two, C
N, formyl, C_Two~ C₆Alkoxycarbonyl, C_Two~
C_FourAlkylcarbonyl, C_Two~ C₆Haloalkylcarbo
Nil, C_Two~ C₆Alkylcarbonyloxy and -NU
¹U^Two1 to 4 substituents arbitrarily selected from
, T¹Is C₁~ C₂₀Alkyl, C_Two~ C₆Alkenyl, C₁
~ C₆Haloalkyl, C _Two~ C_FiveAlkoxyalkyl, C_Three
~ C₆Halocycloalkyl, R^aC substituted with₁~ C_FourA
Luquil, C₁~ C_ThreeC optionally substituted with alkyl_Three
~ C₆Cycloalkyl, R^aC substituted with_Three~ C₆Cyclo
Alkyl, R^aAnd C₁~ C_FourAlkyl-substituted
Clopropyl, R^cAnd C substituted with halogen_Three~ C
_FourCycloalkyl group, R^dAnd C₁~ C_FourSubstitute with alkyl
Cyclopropyl group, R^aC substituted with_Two~ C_FourA
Lucenyl, C₁~ C₁₂Alkoxy, C₁~ C_FourHalo alco
Kissi, C_Two~ C_FiveAlkenyloxy, C₁~ C_ThreeWith alkyl
Optionally substituted C_Three~ C₆Cycloalkoxy, ben
Jiloxy, C_Two~ C_FiveAlkoxycarbonyl, -NU¹
U^Two, Phenylamino, a group optionally substituted with Z
Nil, phenoxy optionally substituted with Z, substituted with Z
Optionally substituted with phenylthio or Z
5 to 5 which may be substituted by good naphthyl or Z
6-membered heterocyclic groups (however, these heterocyclic groups are
, Furyl, pyrrolyl, oxazolyl, isoxazoly
, Thiazolyl, isothiazolyl, pyrazolyl, imida
Zolyl, 1,3,4-oxadiazolyl, 1,2,4-
Oxadiazolyl, 1,3,4-thiadiazolyl, 1,
2,4-thiadiazolyl, 1,2,4-triazolyl,
1,2,3-thiadiazolyl, 1,2,3-triazolyl
1,2,3,4-tetrazolyl, pyridinyl, pyri
Midinyl, pyrazinyl, pyridazinyl, 1,3,5-to
Selected from riadinyl and 1,2,4-triazinyl
It is. ) And T^TwoAnd T^ThreeIs independently OH, phenyl, C₁~ C₆
Alkyl, C₁~ C₆Alkoxy or C₁~ C_FourAlkyl
Sulfphenyl, T^Four, T^FiveAnd T⁶Is independently H, C₁~ C₆Archi
Le, C₁~ C₆Alkenyl, C₁~ C_ThreeSubstituted with an alkyl group
C that may be_Three~ C₆Cycloalkyl group or benzyl
Or T^Four, T^FiveAnd T⁶Two of
Is an oxygen atom together with the nitrogen atom to which each is attached,
5 to 5 which may contain a nitrogen atom or a sulfur atom
X and Z are each independently halogen, C₁~ C_FourArchi
Le, C₁~ C_FourHaloalkyl, C₁~ C_FourAlkoxy, C₁
~ C_FourHaloalkoxy, C₁~ C_FourAlkylsulfeni
Le, C₁~ C_FourAlkylsulfinyl, C₁~ C_FourAlkyl
Sulfonyl, C_Two~ C_FiveAlkenylsulfenyl, C_Two~
C_FiveAlkenylsulfinyl, C_Two~ C_FiveAlkenyl sulf
Honyl, C₁~ C_FourHaloalkylsulfenyl, C₁~ C_Four
Haloalkylsulfinyl, C₁~ C_FourHaloalkylsul
Honyl, NO_Two, CN, CHO, OH, -NU¹U^Two,
Phenyl, phenoxy and C_Two~ C_FiveAlkoxycarboni
1 to 5 substituents arbitrarily selected from
, T⁷And T⁸Are each independently H, phenyl, benzyl or
Or C₁~ C₆Alkyl or T⁷And T⁸And
Form a 5- to 8-membered ring with the carbon atoms
Well, U¹And U^TwoIs independently H, C₁~ C₆Alkyl, C
_Two~ C_FiveAlkylcarbonyl, C_Two~ C_FiveAlkoxycarbo
Nyl, phenyl or benzyl, or U¹And U^TwoAnd
Form a 5- to 8-membered ring with the carbon atoms
Well, R^aIs halogen and C₁~ C_FourSelected from alkyl
Phenyl optionally substituted with one or more kinds,^bIs halogen and C₁~ C_FourSelected from alkyl
Benzoyl optionally substituted with one or more kinds,^cIs halogen and C₁~ C_FourSelected from alkoxy
A phenyl optionally substituted with at least one kind of^dRepresents C which may be substituted with halogen_Two~ C_FourAl
Kenyl. An acrylonitrile compound represented by the formula: 2. The acrylonitrile compound according to claim 1, wherein Q is thiazolyl substituted with R. 3. The acrylonitrile compound according to claim 1, wherein Q is pyrazolyl substituted with R. 4. The acrylonitrile compound according to claim 1, wherein R is pyrimidinyl or pyrazinyl optionally substituted with G. 5. An agrochemical comprising at least one acrylonitrile compound according to claim 1 as an active ingredient.