JP2001089473A - Acrylonitrile compound and pest controlling agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a new agrochemical, especially an insecticide. SOLUTION: This acrylonitrile compound is represented by the formula (1) [Q is a thiazolyl substituted with a specific group or a pyrazolyl substituted with a specified group; A is a phenyl (substituted with a specific group), a naphthyl (substituted with a specified group) or a heterocycle (substituted with a specific group); and B is H, a 1-4C alkyl, a 1-4C haloalkyl or the like], and the agrochemical contains the acrylonitrile compound.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a novel acrylonitrile compound and an agricultural chemical 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 Acrylonitrile derivatives are disclosed as insecticides in JP-A-53-92769, and as pesticides in International Patent Application Publication (WO97 / 40009). JP-A-60-11452 discloses 2- (4-chlorophenyl) -3 as a herbicide.
-(3-pyridyl) -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]

In order to solve the above-mentioned 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

[0007] wherein, Q is wherein R and (R ¹⁾ thiazolyl substituted with n or R and (R ¹⁾ pyrazolyl substituted with n,, A may be substituted with W Phenyl, naphthyl optionally substituted with W or heterocyclic group optionally substituted with Y (provided that the heterocyclic group is thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl,
1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-
Thiadiazolyl, 1,2,4-triazolyl, 1,2,2
3-thiadiazolyl, 1,2,3-triazolyl, 1,
2,3,4-tetrazolyl, pyridyl, pyrimidinyl,
Pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, indazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl. And B is H, C ₁ -C ₄ alkyl, C
₁ -C ₄ haloalkyl, C ₂ -C ₄ alkoxyalkyl alkyl, C
_{H 3 SCH 2, CH 3 OC} 2 H 4 OCH 2, C substituted with R ^a ₁ -C ₄ alkyl, have been C ₁ -C ₄ alkyl substituted with R ^b, tetrahydropyranyl, (CH _{3) 3} Si , C ₁ -C ₄
Alkylsulfonyl, halogen or C ₁ -C ₄ phenyl sulfonyl optionally substituted by alkyl, -SO
₂ CF _3, C _{1 ~C 4} monoalkylamino aminosulfonyl, C ₂
-C ₈ dialkylaminosulfonyl, phenylaminosulfonyl, C ₂ -C ₅ mono alkylaminothiocarbonyl, C ₃ -C ₉ dialkylaminothiocarbonyl, C ₂ ~
C ₅ cyanoalkyl, 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 or NHT ⁴ T ⁵ T ⁶ ,

R is a heterocyclic group which may be substituted by G
(However, this heterocyclic group is 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
, Pyrimidinyl, pyrazinyl, pyridazinyl, 1,
3,5-triazinyl, 1,2,4-triazinyl,
Nzothiazolyl, benzimidazolyl, indazolyl,
Benzoxazolyl, quinolinyl, isoquinolinyl,
Noxalinyl, phthalazinyl, cinnolinyl or quina
Zolinyl. ) And R¹Is halogen, C₁~ C
_TenAlkyl, C₁~ C_FiveAlkoxycarbonyl, NO _Two,
CN, -NU¹U^TwoOr -N = CT⁷T⁸Where n is
W is an integer of 0 or 1;₁~ C_Ten
Alkyl, R^aC substituted with₁~ C_FourAlkyl, C _Two~ C
₆Alkenyl, C_Two~ C₆Alkynyl, C₁~ C₆Haloa
Luquil, C_Two~ C₆Haloalkenyl, C_Two~ C₆Haloalk
Nil, C_Three~ C₆Halocycloalkyl, C₁~ C_ThreeAlkyl
C optionally substituted with_Three~ C₆Cycloalkyl, C₁
~ C₆Alkoxy, C_Two~ C₆Alkenyloxy, C_Two~ C
₆Alkynyloxy, C₁~ C_FourHaloalkoxy, C_Two~ C
₆Haloalkenyloxy, C_Two~ C₆Haloalkynyloxy
Si, C ₁~ C_FourAlkylsulfenyl, C₁~ C_FourAlkyl
Sulfinyl, C₁~ C_FourAlkylsulfonyl, C_Two~ C₆
Alkenylsulfenyl, C_Two~ C₆Alkenyl sulphie
Nil, C_Two~ C₆Alkenylsulfonyl, C_Two~ C₆Archi
Nilsulfenyl, C_Two~ C₆Alkynyl sulfini
Le, C_Two~ C₆Alkynylsulfonyl, C₁~ C_FourHaloal
Killsulfenyl, C₁~ C_FourHaloalkylsulfini
Le, C₁~ C_FourHaloalkylsulfonyl, C_Two~ C₆Haloa
Lucenylsulfenyl, C_Two~ C₆Haloalkenyl sulf
Inil, C_Two~ C₆Haloalkenylsulfonyl, C_Two~ C₆
Haloalkynylsulfenyl, C_Two~ C₆Haloalkynyl
Sulfinyl, C_Two~ C₆Haloalkynylsulfonyl, N
O_Two, CN, -NU¹U^Two, Phenoxy, OH, nafti
Le, C_Two~ C₇Alkoxycarbonyl, C_Two~ C_FourAlkoki
Sialkyl, C_Two~ C_FourAlkylcarbonyl, C_Two~ C_FiveA
Alkylcarbonyloxy, C_Two~ C_FiveHaloalkylcarbo
Nyloxy, benzoyl optionally substituted with X, X
Phenyl optionally substituted with X,
Pyridyl, thienyl optionally substituted with X,
And -N = CT⁷T⁸1 to 4 arbitrarily selected from
Substituents, or alkyl linked at adjacent substitution positions
A 5- to 8-membered ring formed by ren,

Y is halogen, C₁~ C_TenAlkyl, C₁
~ C₆Haloalkyl, C₁~ C₆Alkoxy, C_Two~ C₆A
Lucenyloxy, C_Two~ C₆Alkynyloxy, C₁~ C_Four
Haloalkoxy, C_Two~ C₆Haloalkenyloxy, C_Two
~ C₆Haloalkynyloxy, C₁~ 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~ C₆Alkynylsulfoni
Le, C₁~ C_FourHaloalkylsulfenyl, C₁~ C_FourHalo
Alkylsulfinyl, C₁~ C_FourHaloalkylsulfoni
Le, C_Two~ C₆Haloalkenylsulfenyl, C_Two~ C₆C
Loalkenylsulfinyl, C_Two~ C₆Haloalkenyls
Ruphonyl, C_Two~ C₆Haloalkynylsulfenyl, C_Two
~ C₆Haloalkynylsulfinyl, C_Two~ C₆Haloal
Quinylsulfonyl, NO_Two, CN, -NU¹U^Two, OH,
C_Two~ C₇Alkoxycarbonyl, C_Two~ C_FourAlkoxya
Luquil, C_Two~ C_FiveAlkylcarbonyloxy, C_Two~ C_Five
Haloalkylcarbonyloxy, C_Three~ C₇Dialkylur
Minocarbonyloxy, a group optionally substituted with X
Nil, and -N = CT⁷T⁸(However, T⁷And T⁸Are each
Independently, H, phenyl, benzyl or C₁~ C₆Archi
Or T⁷And T⁸Together with the carbon atom to which
It may form a 5- to 8-membered ring. )
1 to 4 substituents or adjacent substitution positions
5 to 8 members formed by alkylene linked by
G is a halogen, C₁~ C₆Alkyl, C₁~
C_FourHaloalkyl, C₁~ C_FourAlkoxy, C₁~ C_FourHalo
Alkoxy, C₁~ C_FourAlkylsulfenyl, C₁~ C_Four
Alkylsulfinyl, C₁~ C_FourAlkylsulfonyl,
C₁~ C_FourHaloalkylsulfenyl, C₁~ C_FourHaloal
Killsulfinyl, C₁~ C_FourHaloalkylsulfonyl,
C_Two~ C_FourAlkenyl, C_Two~ C_FourHaloalkenyl, C_Two~
C_FourAlkenyloxy, C_Two~ C_FourHaloalkenyloxy
Si, C_Two~ C_FourAlkenylsulfenyl, C_Two~ C_FourArche
Nilsulfinyl, C_Two~ C_FourAlkenylsulfonyl, C
_Two~ C_FourHaloalkenylsulfenyl, C_Two~ C_FourHaloal
Kenylsulfinyl, C_Two~ C_FourHaloalkenylsulfoni
Le, C_Two~ C_FourAlkynyl, C_Two~ C_FourHaloalkynyl, C
_Two~ C_FourAlkynyloxy, C_Two~ C_FourHaloalkynyloxy
Si, C_Two~ C_FourAlkynylsulfenyl, C_Two~ C_FourArchi
Nilsulfinyl, C_Two~ C_FourAlkynylsulfonyl, C
_Two~ C_FourHaloalkynylsulfenyl, C_Two~ C_FourHaloal
Quinylsulfinyl, C_Two~ C_FourHaloalkynylsulfoni
Le, NO_Two, CN, formyl, C_Two~ C₆Alkoxycal
Bonil, C_Two~ C_FourAlkylcarbonyl, C_Two~ C₆Haloa
Alkylcarbonyl, C_Two~ C₆Alkylcarbonyloxy
And -NU¹U^Two1 to 4 arbitrarily selected from
Is a substituent of

[0010] T¹Is C₁~ C₂₀Alkyl, C_Two~ C₆Al
Kenil, C₁~ C₆Haloalkyl, C _Two~ C_FiveAlkoxya
Luquil, C_Three~ C₆Halocycloalkyl, R^aIs replaced by
C₁~ C_FourAlkyl, C₁~ C_ThreeSubstituted with alkyl
May be C_Three~ C₆Cycloalkyl, R^aC substituted with_Three
~ C₆Cycloalkyl, R^aAnd C₁~ C_FourAlkyl
Substituted cyclopropyl, Rc and halogen
C_Three~ C_FourCycloalkyl, R^dAnd C₁~ C_FourAl
A cyclopropyl substituted with a kill, R^aC substituted with_Two
~ C_FourAlkenyl, C₁~ C₁₂Alkoxy, C₁~ C_FourHalo
Alkoxy, C_Two~ C_FiveAlkenyloxy, C₁~ C_ThreeAl
C which may be substituted by kill_Three~ C₆Cycloalkoxy
Si, benzyloxy, C_Two~ C_FiveAlkoxycarbonyl,
-NU¹U^Two, Phenylamino, may be substituted with Z
Phenyl, phenoxy optionally substituted with Z, Z
Optionally substituted with phenylthio, substituted with Z
5 optionally substituted with naphthyl or Z
Or a 6-membered heterocyclic group (however, these heterocyclic groups are
Enyl, furyl, pyrrolyl, oxazolyl, isoxazo
Ril, thiazolyl, isothiazolyl, pyrazolyl, imi
Dazolyl, 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-tria
Zolyl, 1,2,3,4-tetrazolyl, pyridyl, pi
Limidinyl, pyrazinyl, pyridazinyl, 1,3,5-
Select from triazinyl and 1,2,4-triazinyl
Devour. ) And T^TwoAnd T^ThreeIs independently OH,
Phenyl, C₁~ C₆Alkyl, C₁~ C₆Alkoxy or
Is C₁~ C_FourAlkylsulfenyl, T^Four, T^Fiveas well as
T⁶Is independently H, C₁~ C₆Alkyl, C₁~ C₆
Alkenyl, C₁~ C_ThreeOptionally substituted with alkyl
C_Three~ C₆Is or is cycloalkyl or benzyl
Or T^Four, T^FiveAnd T⁶Two of each are joined
Oxygen, nitrogen or sulfur with nitrogen
Form a 5- to 8-membered ring group optionally containing atoms
X and Z are each independently halogen, C
₁~ C_FourAlkyl, C₁~ C_FourHaloalkyl, C₁~ C_FourAl
Coxy, C₁~ C_FourHaloalkoxy, C₁~ C_FourAlkyls
Luphenyl, C₁~ C_FourAlkylsulfinyl, C₁~ C_Four
Alkylsulfonyl, C_Two~ C_FiveAlkenylsulfeni
Le, C_Two~ C_FiveAlkenylsulfinyl, C_Two~ C_FiveArche
Nylsulfonyl, C₁~ C_FourHaloalkylsulfenyl,
C₁~ C_FourHaloalkylsulfinyl, C₁~ C_FourHaloal
Killsulfonyl, NO_Two, CN, CHO, OH, -NU¹
U^Two, Phenyl, phenoxy and C_Two~ C_FiveAlkoxy
1 to 5 substitutions arbitrarily selected from carbonyl
Group,

T ⁷ and T ⁸ are each independently H, phenyl, benzyl or C ₁ -C ₆ alkyl, or 5 to 8 together with the carbon atom to which T ⁷ and T ⁸ are bonded.
U ¹ and U ² may each independently be
H, C ₁ -C ₆ alkyl, C ₂ -C ₅ alkylcarbonyl,
_{May be} C ₂ -C ₅ alkoxycarbonyl, phenyl or benzyl, or may form a 5- to 8-membered ring with the carbon atom to which U ¹ and U ² are attached, and ^Ra is halogen and C ₁ -C ₅ a C ₄ phenyl optionally substituted with one or more selected from alkyl, R ^b is located may benzoyl optionally substituted by one or more members selected from halogen and C ₁ -C ₄ alkyl, Rc is , Halogen and C ₁
Phenyl which may be substituted with one or more kinds selected from ＣC ₄ alkoxy, and R ^d is C ₂ ＣC ₄ alkenyl which may be substituted with halogen. An acrylonitrile compound represented by the formula:

[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.

[0016]

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

[0017]

Embedded image

It will be understood that they may exist in tautomeric forms represented by The compound is believed 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, R ¹ , Y, W,
^{X, Z, T 1, T} 2, T 3, T 4, T 5, T 6, T 7, T 8, U
Preferred ranges of ¹ and U ² will be described.

However, the following heterocyclic groups in AI to AIV, RI to RIII, and T ¹ I to T ¹ III have the following meanings. That is, thienyl is thiophen-2-yl or thiophen-3-yl, furyl is furan-2-yl or furan-3-yl, and pyrrolyl is pyrrol-1-yl, pyrrol-2-yl. Il, pyrrole
3-yl and oxazolyl is oxazol-2-yl, oxazol-4-yl or oxazol-5
And thiazolyl is thiazol-2-yl, thiazol-4-yl or thiazol-5-yl;
Imidazolyl is imidazol-1-yl, imidazol-2-yl or imidazol-4-yl; isoxazolyl isoxazol-3-yl, isoxazol-4-yl or isoxazol-5-yl;
Isothiazolyl is isothiazol-3-yl, isothiazol-4-yl or isothiazol-5-yl, and pyrazolyl is pyrazol-1-yl, pyrazol-yl.
3-yl, pyrazol-4-yl or pyrazol-5
-Yl and 1,3,4-oxadiazolyl is 1,1
3,4-oxadiazol-2-yl,
4-thiadiazolyl is 1,3,4-thiadiazole-2
-Yl and 1,2,4-oxadiazolyl is 1,
2,4-oxadiazol-3-yl or 1,2,4
-Oxadiazol-5-yl, 1,2,4-thiadiazolyl is 1,2,4-thiadiazol-3-yl or 1,2,4-thiadiazol-5-yl,
1,2,4-triazolyl is 1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl or 1,2,4-triazol-4-yl;
2,3-thiadiazolyl is 1,2,3-thiadiazol-4-yl or 1,2,3-thiadiazol-5-yl,

1,2,3-triazolyl is 1,2,3-
Triazol-1-yl, 1,2,3-triazole-
2-yl or 1,2,3-triazol-4-yl, and 1,2,3,4-tetrazolyl is 1,2,3,4
-Tetrazol-1-yl, 1,2,3,4-tetrazol-2-yl or 1,2,3,4-tetrazole-
5-yl, pyridyl is pyridin-2-yl, pyridin-3-yl or pyridin-4-yl, pyrimidinyl is pyrimidin-2-yl, pyrimidin-4-yl or pyrimidin-5-yl, Pyrazinyl is pyrazin-2-yl; pyridazinyl is pyridazin-
3-yl or pyridazin-4-yl;
5-Triazinyl is 1,3,5-triazin-2-yl and 1,2,4-triazinyl is 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl or 1,2,4-triazin-6-yl.

Preferred ranges of A are the following groups.

AI: phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,3-thiadiazolyl, pyridyl , Pyrimidinyl, pyrazinyl and pyridazinyl.

AII: phenyl, thiazolyl, pyrazolyl, pyridyl and pyrimidinyl.

AIII: Thiazolyl, pyrazolyl and pyridyl.

AIV: thiazolyl. AV: pyrazolyl. AV
I: pyridyl.

Preferred ranges of B are the following groups.

That is, BI: H, C ₁ -C ₄ alkyl, C ₁ -C ₄
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 phenyl sulfonyl optionally substituted by one or more selected from alkyl, -SO ₂ C
F 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, alkaline earth metal atom and NHT ⁴ T ⁵ T ⁶ .

BIV: C ₂ -C ₄ alkoxyalkyl, C ₁
-C _{4 alkylsulfonyl, -SO 2 CF 3, -C (} =
O) T ¹ , alkali metal atoms, alkaline earth metal atoms and NHT ⁴ T ⁵ T ⁶ .

Preferred ranges of G are the following groups.

That is, GI: halogen, C₁~ C₆Archi
Le, C_Two~ C_FourAlkenyl, C_Two~ C_FourAlkynyl, C₁~
C_FourHaloalkyl, C_Two~ C_FourHaloalkenyl, C_Two~ C_Four
Haloalkynyl, C₁~ C_ThreeEven if substituted with alkyl
Good C_Three~ C₆Cycloalkyl, C ₁~ C₆Alkoxy, C
_Two~ C_FourAlkenyloxy, C_Two~ C_FourAlkynyloxy,
C ₁~ C_FourHaloalkoxy, C_Two~ C_FourHaloalkenyloxy
Si, C_Two~ C_FourHaloalkynyloxy, C₁~ C_FourAlkyl
Sulfenyl, C₁~ C_FourAlkylsulfinyl, C ₁~
C_FourAlkylsulfonyl, C_Three~ C_FourAlkenyl sulfe
Nil, C_Three~ C_FourAlkenylsulfinyl, C_Three~ C_FourAl
Kenylsulfonyl, C_Three~ C_FourAlkynylsulfenyl,
C_Three~ C_FourAlkynylsulfinyl, C_Three~ C_FourAlkynyl
Sulfonyl, C ₁~ C_FourHaloalkylsulfenyl, C₁
~ C_FourHaloalkylsulfinyl, C₁~ C_FourHaloalk
Rusulfonyl, C_Three~ C_FourHaloalkenylsulfenyl,
C_Three~ C_FourHaloalkenylsulfinyl, C_Three~ C_FourHaloa
Lucenylsulfonyl, C_Three~ C_FourHaloalkynyl sulfe
Nil, C_Three~ C_FourHaloalkynylsulfinyl, C_Three~ C_Four
Haloalkynylsulfonyl, NO_Two, CN, -NU
¹U^Two, Halogen or C₁~ C _FourSubstituted with alkyl
Optionally substituted phenyl substituted methoxy, C_Two~ C₆A
Lucoxycarbonyl, C_Two~ C_FourAlkoxyalkyl, C
_Two~ C_FourAlkylcarbonyl, C_Two~ C_FourHaloalkylcal
Bonil, C_Two~ C_FiveAlkylcarbonyloxy, C _Two~ C_Five
Haloalkylcarbonyloxy, C_Three~ C₇Dialkylur
Minocarbonyloxy, a group optionally substituted with Z
Nil, phenoxy optionally substituted with Z, substituted with Z
Benzoyl, which may be substituted with Z
Pyridyl and pyridyl oxo optionally substituted with Z
A substituent arbitrarily selected from the following (provided that the substituent is
In the case of two or more, they may be the same or different from each other. )
Thus, the number of the substituents is 1, 2, 3 or 4
Or by an alkylene attached at an adjacent
, 6-, 7- or 8-membered ring formed by
It is.

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 O ₂ , —NU ¹ U ² and phenyl optionally substituted with 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.

The 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 ₁₀ alkyl, C ₁ -C ₅ alkoxycarbonyl, NO ₂ , CN,-
^{NU 1 U 2, -N = CT} 7 T 8.

R ¹ II: halogen, C ₁ -C ₁₀ alkyl, 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
Halo alkynylsulfonyl, 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 halo alkylcarbonyloxy or optionally selected substituents from among phenyl optionally substituted by X (provided that the substituents may be different in the same or mutually in the case of two or more.) In The number of the 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 substituents is 1, 2 or 3
is there.

The number of Y differs depending on the type of the 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 pyridyl, the number of Y is an integer of 0 to 4, preferably an integer of 0 to 3, and more preferably 1 or 2.

Preferred ranges of W are the following groups.

That is, WI: halogen, C₁~ C₆Archi
Le, C₁~ C_FourHaloalkyl, C₁~ C_FourAlkoxy, C₁
~ C_FourHaloalkoxy, C₁~ C_FourAlkylsulfeni
Le, C₁~ C_FourAlkylsulfinyl, C₁~ C_FourAlkyl
Sulfonyl, C₁~ C_FourHaloalkylsulfenyl, C₁
~ C_FourHaloalkylsulfinyl, C₁~ C_FourHaloalk
Rusulfonyl, C_Three~ C_FourAlkenyloxy, C_Three~ C_FourC
Loalkenyloxy, C_Three~ C_FourAlkenylsulfeni
Le, C_Three~ C_FourAlkenylsulfinyl, C_Three~ C_FourArche
Nylsulfonyl, C_Three~ C_FourHaloalkenylsulfeni
Le, C_Three~ C_FourHaloalkenylsulfinyl, C_Three~ C_FourC
Loalkenylsulfonyl, C_Three~ C_FourAlkynyloxy,
C_Three~ C_FourAlkynylsulfenyl, C_Three~ C_FourAlkynyl
Sulfinyl, C _Three~ C_FourAlkynylsulfonyl, N
O_Two, CN, C_Two~ C_FourAlkoxycarbonyl, C_Two~ C_Four
Alkylcarbonyl, C_Two~ C_FourHaloalkylcarboni
Le, C_Two~ C_FourAlkylcarbonyloxy and -NU¹U^Twoof
A substituent arbitrarily selected from the following (provided that two
In the above cases, they may be the same or different from each other. )
And 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 is, 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 substituted by phenyl optionally substituted by C ₁ -C ₄ alkyl
₁ -C ₄ alkyl, C ₃ -C ₆ halocycloalkyl, C ₁ ~
C ₃ alkyl substituted optionally C ₃ even though -C ₆ cycloalkyl, halogen or C ₁ -C ₄ C ₃ substituted in phenyl substituted with alkyl -C ₆ cycloalkyl, halogen or C ₁ -C ₄ alkyl unsubstituted or substituted with phenyl optionally a 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 alkoxycarbonyl, —NU ¹ U ² , Z Good phenyl, phenoxy optionally substituted with Z, phenylthio optionally substituted with Z, naphthyl or a heterocyclic group optionally substituted with Z (provided that the 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, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,
It is selected from 3,5-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_FourSubstituted with alkyl
Optionally substituted phenyl substituted C_Two~ C_FourAlkene
Le, C₁~ C_TenAlkoxy, C₁~ C_FourHaloalkoxy,
C_Three~ C_FiveAlkenyloxy, C_Three~ C₆Cycloalkoxy
Si, benzyloxy, C_Two~ C_FiveAlkoxycarbonyl,
Phenyl optionally substituted with Z, substituted with Z
Phenoxy, phenylthio, naphthyl or Z
A heterocyclic group which may be substituted with
Is thienyl, furyl, oxazolyl, thiazolyl, pyra
It is selected from zolyl or pyridyl. ).

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 pyridyl optionally substituted by Z.

The preferred range of T ² is the following group.

That is, T ² I is phenyl, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylsulfenyl.

The preferred range of T ³ is the following group.

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 or cycloalkyl or benzyl, or two of T ^4, T ⁵ and T ⁶ is an oxygen atom together with the nitrogen atom to which each is attached, also contain a nitrogen atom or a sulfur atom It forms a good 5-, 6- or 7-membered ring group.

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 or cycloalkyl or benzyl, or two of T ^4, T ⁵ and T ⁶ is an oxygen atom together with the nitrogen atom to which each is attached, also contain a nitrogen atom or a sulfur atom It forms a good 5-, 6- or 7-membered ring group.

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 or cycloalkyl or benzyl, or two of T ^4, T ⁵ and T ⁶ is an oxygen atom together with the nitrogen atom to which each is attached, also contain a nitrogen atom or a sulfur atom It forms a good 5-, 6- or 7-membered ring group, and the preferred range of X is the following groups.

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
A substituent arbitrarily selected from haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, NO ₂ , CN, —NU ¹ U ² or C ₂ -C ₅ alkoxycarbonyl (provided that the number of substituents 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
-C ₄ haloalkyl, a C ₁ -C ₄ alkoxy, optionally selected substituents from among (provided that the substituent is in the case of two or more may be different in the same or another.), The substituent The number of groups is one or two.

The number of X differs depending on the ring substituted by X.
When the ring is phenyl, the number of X is an integer from 0 to 5, preferably an integer from 0 to 3. When the ring is pyridyl, the number of X is an integer from 0 to 4, preferably 0, 1 or 2, more preferably 0 or 1.
It is. In the case of thienyl, the number of X is an integer from 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
A substituent arbitrarily selected from haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, NO ₂ , CN, —NU ¹ U ² or C ₂ -C ₅ alkoxycarbonyl (provided that the number of substituents is two or more; May be the same or different from each other), and 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 of 0 to 3, preferably an integer of 0 to 2, and more preferably 1 or 2. When the heterocyclic ring is pyrrolyl or pyridyl, 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, it is T ⁷ I: H, phenyl, benzyl or C ₁ -C ₄ alkyl, or forms a 5- or 6-membered ring with the carbon atom to which T ⁷ and T ⁸ are bonded. .

Preferred ranges of T ⁸ are the following groups.

That is, T ⁸ I: phenyl, benzyl or C
₁ -C ₄ alkyl or is, or 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 alkylcarbonyl, or a 5-membered or 6-membered ring together with a carbon atom to which U ¹ and U ² are bonded. , A 7-membered ring.

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 or 6-membered ring together with a carbon atom to which U ¹ and U ² are bonded. , A 7-membered ring.

Each group in the above-mentioned preferred substituent range can be arbitrarily combined, and the particularly preferred range of the compound of the present invention is described below.

That is, the preferred range of the substituent is AI, BI,
GI, RI, R ¹ I, nI, YI, WI, T ¹ I, T ² I, T
^The compounds of the present invention which are 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.

Preferred ranges of the substituents are 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 ranges of the substituents are AII, BI, GII
I, RI, nII, YI, WI, T ¹ I, T ² I, T ³ I, T ⁴ I, T
^The compound of the present invention, which is ⁵ I, T ⁶ I, XI, ZI, T ⁷ I, T ⁸ I, U ¹ I and U ² I.

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.

The preferred range of the substituent is AIII, BII, GI
^{I, RII, R 1 II,} nI, YII, T 1 II, T 2 I, T 3 I, T
⁴ I, T ⁵ I, T ⁶ I, XII, ZII, 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, 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.

Preferred ranges of the substituents are AIII, BIII, G
III, RIII, nII, YII, T 1 III, T 2 I, T 3 I, T 4 I,
The compound of the present invention, which is T ⁵ I, T ⁶ I, XIII, ZII, T ⁷ I, T ⁸ I, U ¹ I and U ² I.

The preferred range of the substituent is AIV, BIII, GI
II, RIII, nII, YII, T 1 III, T 2 I, T 3 I, T 4 I,
The compound of the present invention, which is T ⁵ I, T ⁶ I, XIII, ZII, T ⁷ I, T ⁸ I, U ¹ I and U ² I.

Preferred ranges of the substituents are 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 ranges of the substituents are 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 ranges of the substituents are AV, BIII and 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.

The 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 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 ranges of the substituents are AVI and BII.
I, GIII, RIII, nII, YII, T 1 III, T 2 I, T 3 I,
The compound of the present invention, which is T ⁴ I, T ⁵ I, T ⁶ I, XIII, ZII, T ⁷ I, T ⁸ I, U ¹ I and U ² I.

Preferred ranges of the substituents are AVI, BIV and 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 ranges of the substituents are AVI, BIV and 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.

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.

The halogen atom in the definition of G, R ¹ , W, X, Y or Z includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a fluorine atom, a chlorine atom and a bromine atom. Can be

B, R ¹ , G, T ¹ , T ² , T ³ , T ⁴ , T ⁵ ,
Alkyl in the definition of T ⁶ , T ⁷ , T ⁸ , U ¹ , U ² , W, X, Y or Z is methyl, ethyl, n-propyl, isopropyl, n-butyl as a linear or branched alkyl. , Isobutyl, tert-butyl, se
c-butyl, pentyl-1, pentyl-2, pentyl-
3,2-methylbutyl-1,2-methylbutyl-2,2
-Methylbutyl-3,3-methylbutyl-1,2,2-
Dimethylpropyl-1, hexyl-1, hexyl-2,
Hexyl-3, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1
-Dimethylbutyl, 1,2-dimethylbutyl, 1,3-
Dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-
1-methylpropyl, 1-ethyl-2-methylpropyl, 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.

The alkenyl in the definition of G, T ¹ , T ⁴ , T ⁵ , T ⁶ or W is ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl as straight-chain or branched alkenyl. , 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 in the definition of G or W includes ethynyl as a linear or branched alkynyl,
1-propynyl, 2-propynyl, 1-butynyl, 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, each having the specified number of carbon atoms Is selected from the range.

The haloalkyl in the definition of B, G, T ¹ , W, X, Y or Z includes, as a linear or branched haloalkyl, fluoromethyl, chloromethyl, bromomethyl, fluoroethyl, chloroethyl, bromoethyl, fluoro-n -Propyl, chloro-n-propyl,
Difluoromethyl, chlorodifluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, difluoroethyl, trifluoroethyl, trichloroethyl, chlorodifluoromethyl, bromodifluoromethyl, trifluorochloroethyl, hexafluoro-n-propyl, chlorobutyl, fluoro Butyl, chloro-n-
Pentyl, fluoro-n-pentyl, chloro-n-hexyl, fluoro-n-hexyl and the like can be mentioned, and each is selected from the designated carbon number range.

[0104] ^{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
Examples of cycloalkyl include cyclopropyl, 1-methylcyclopropyl, 2,2,3,3-tetramethylcyclopropyl, cyclobutyl, 1-ethylcyclobutyl,
Examples thereof include 1-n-butylcyclobutyl, cyclopentyl, 1-methylcyclopentyl, cyclohexyl, 1-methylcyclohexyl, and 4-methylcyclohexyl.

The C ₁ -C ₄ alkyl substituted with ^Ra in the definition of B, W or T ¹ includes benzyl, 2-chlorobenzyl, 3-bromobenzyl, 4-chlorobenzyl, 4-methylbenzyl, 4-tert-butylbenzyl, 1-phenylethyl, 1- (3-chlorophenyl) ethyl, 2-phenylethyl, 1-methyl-1-phenylethyl, 1- (4-chlorophenyl) -1-methylethyl, 1- (3-chlorophenyl) -1-methylethyl, 1-phenylpropyl, 2-phenylpropyl,
3-phenylpropyl, 1-phenylbutyl, 2-phenylbutyl, 3-phenylbutyl, 4-phenylbutyl, 1-methyl-1-phenylpropyl, 1-methyl-
2-phenylpropyl, 1-methyl-3-phenylpropyl, 2-methyl-2-phenylpropyl, 2- (4-
Chlorophenyl) -2-methyl-propyl, 2-methyl-2- (3-methylphenyl) propyl and the like.

C ₃ substituted by R ^a in the definition of T ¹
-C ₆ cycloalkyl includes 1-phenylcyclopropyl, 1- (3-chlorophenyl) cyclopropyl,
1- (4-chlorophenyl) cyclopropyl, 1- (4
-Bromophenyl) cyclopropyl, 1- (4-fluorophenyl) cyclopropyl, 1- (4-ethylphenyl) cyclopropyl, 1- (4-propylphenyl) cyclopropyl, 2-phenylcyclopropyl, 1-phenylcyclo Butyl, 2-phenylcyclobutyl, 1-phenylcyclopentyl, 1- (4-chlorophenyl) cyclopentyl, 2-phenylcyclopentyl, 3-phenylcyclopentyl, 1-phenylcyclohexyl,
1- (3-fluorophenyl) cyclohexyl, 1-
(4-chlorophenyl) cyclohexyl, 1- (4-tert-butylphenyl) cyclohexyl, 2-phenylcyclohexyl, 3-phenylcyclohexyl,
-Phenylcyclohexyl and the like.

In the definition of T ¹ , cyclopropyl substituted with R ^a and C ₁ -C ₄ alkyl includes 2,2-
Dimethyl-1-phenylcyclopropyl, 1- (4-chlorophenyl) -2,2-dimethylcyclopropyl,
2,2-dimethyl-3-phenylcyclopropyl, 3-
(3-chlorophenyl) -2,2-dimethylcyclopropyl, (4-chlorophenyl) -2,2-dimethyl-3
-Phenylcyclopropyl, (4-bromophenyl)-
2,2-dimethyl-3-phenylcyclopropyl, 2,
2-dimethyl-3- (4-methylphenyl) cyclopropyl, (4-tert-butylphenyl) -2,2-
Dimethyl-3-phenylcyclopropyl and the like.

In the definition of T ¹ , R _{3 and} C ₃ -C ₄ cycloalkyl substituted with a halogen atom include:
2,2-dichloro-1-phenylcyclopropyl, 2,
2-dichloro-1- (3-chlorophenyl) cyclopropyl, 2,2-dichloro-1- (4-methoxyphenyl) cyclopropyl, 2,2-dichloro-1- (4-ethoxyphenyl) cyclopropyl, 2, 2-dichloro-
1- (4-i-propyloxyphenyl) cyclopropyl, 2,2-dichloro-1- (4-t-butylphenyl) cyclopropyl, 2,2-dichloro-1- (4-methoxyphenyl) -3- Phenylcyclopropyl, 1-
(4-ethoxyphenyl) -2,2,3,3-tetrafluorobutyl and the like.

Rc and C ₁ -C ₄ in the definition of T ¹
As cyclopropyl substituted with alkyl, 2,2
-Dimethyl-3- (2,2-dimethylethenyl) cyclopropyl, 3- (2,2-dibromoethenyl) -2,2
-Dimethylcyclopropyl, 3- (2,2-dichloroethenyl) -2,2-dimethylcyclopropyl, 3-
(2,2-chlorotrifluoroethenyl) -2,2-dimethylcyclopropyl and the like.

C ₃ -C ₆ cycloalkoxy optionally substituted by C ₁ -C ₃ alkyl in the definition of T ¹ includes:
Cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexyloxy, 1-methylcyclopropoxy and the like.

C ₂ substituted for R ^a in the definition of T ¹
-C ₄ alkenyl as 1-phenylethenyl,
2-phenylethenyl, 2- (2-chlorophenyl) ethenyl, 2- (3-chlorophenyl) ethenyl, 2-
(4-chlorophenyl) ethenyl, 2- (4-methylphenyl) ethenyl, 2- (2,6-difluorophenyl) ethenyl, 2- (2,5-dimethylphenyl) ethenyl, 1-methyl-2-phenylethenyl , 2-phenyl-1-propenyl, 2- (4-bromophenyl) -1
-Propenyl, 2- (2,4,6-trimethylphenyl) -1-propenyl and the like.

G, T ¹ , T ² , T ³ , W, X, Y or Z
Examples of the alkoxy in the definition of methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, as linear or branched alkoxy
sec-butoxy, tert-butoxy, n-pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethyl Propoxy, 1-ethylpropyloxy, n-hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutyloxy, 1,2
-Dimethylbutyloxy, 1,3-dimethylbutyloxy, 2,2-dimethylbutyloxy, 2,3-dimethylbutyloxy, 3,3-dimethylbutyloxy, 1-ethylbutyloxy, 2-ethylbutyloxy, , 1,
2-trimethylpropyloxy, 1,2,2-trimethylpropyloxy, 1-ethyl-1-methylpropyloxy, 1-ethyl-2-methylpropyloxy, n-heptyloxy, n-octyloxy, n-nonyloxy, n-decyloxy and the like, and each is selected from the specified carbon number range.

C ₃ -C ₆ halocycloalkyl in the definition of W or T ¹ includes fluorocyclopropyl,
Difluorocyclopropyl, chlorocyclopropyl, dichlorocyclopropyl, 1-methyl-2,2-dichlorocyclopropyl, chlorocyclobutyl, dichlorocyclobutyl, chlorocyclopentyl, dichlorocyclopentyl, chlorocyclohexyl, dichlorocyclohexyl,
Tetrafluorocyclobutyl and the like.

-NU ¹ U ² in the definition of G, R ¹ , T ¹ , W, X, Y or Z includes methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec-butylamino, tert-butylamino, n-pentylamino, 1
-Methylbutylamino, 2-methylbutylamino, 3-
Methylbutylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, n-hexylamino, 1-methylpentylamino, 2-methylpentylamino , 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino,
1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino,
1-ethylbutylamino, 2-ethylbutylamino,
1,1,2-trimethylpropylamino, 1,2,2-
Trimethylpropylamino, 1-ethyl-1-methylpropylamino, 1-ethyl-2-methylpropylamino, dimethylamino, diethylamino, di-n-propylamino, diisopropylamino, di-n-butylamino, di-sec- Butylamino, diisobutylamino,
Di-n-pentylamino, di-n-hexylamino, methylethylamino, methylpropylamino, methylisopropylamino, methylbutylamino, methyl-sec
-Butylamino, methylisobutylamino, methyl-t
ert-butylamino, methylpentylamino, methylhexylamino, ethylpropylamino, ethylisopropylamino, ethylbutylamino, ethyl-sec-
Butylamino, ethylisobutylamino, ethylpentylamino, ethylhexylamino, phenylamino, benzylamino, N-methylacetamide, N-ethylacetamide, N-phenylacetamide, N-acetylacetamide, and the like; Is selected in the range.

The alkoxycarbonyl in the definitions of G, R ¹ , T ¹ , W, X, Y and Z includes methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, iso-propoxycarbonyl, n-butoxycarbonyl, sec-butoxycarbonyl Examples thereof include carbonyl, iso-butoxycarbonyl, tert-butoxycarbonyl, n-pentyloxycarbonyl, n-hexyloxycarbonyl and the like, and each is selected within the range of the specified number of carbon atoms.

The C ₁ -C ₄ haloalkoxy in the definition of G, T ¹ , W, X, Y and Z includes C ₁ -C ₄ straight-chain or branched-chain haloalkoxy. Methoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, dichlorofluoromethoxy, chloromethoxy,
Dichloromethoxy, trichloromethoxy, bromomethoxy, fluoroethoxy, chloroethoxy, bromoethoxy, difluoroethoxy, trifluoroethoxy, tetrafluoroethoxy, pentafluoroethoxy, trichloroethoxy, trifluorochloroethoxy, fluoropropoxy, chloropropoxy, bromopropoxy, Fluorobutoxy, chlorobutoxy, fluoro-iso-
And propoxy and chloro-iso-propoxy.

C ₁ -C ₄ alkylsulfenyl in the definition of G, T ² , T ³ , W, X, Y and Z includes methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, iso- Butylthio, sec
-Butylthio and tert-butylthio.

In the definition of G, X, W, Y and Z, C ₁ to
Examples of C ₄ alkylsulfinyl include methylsulfinyl, ethylsulfinyl, n-propylsulfinyl,
iso-propylsulfinyl, n-butylsulfinyl, iso-butylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl.

The C ₁ -C ₄ alkylsulfonyl in the definition of B, G, W, X, Y and Z includes methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, is
o-propylsulfonyl, n-butylsulfonyl, is
o-butylsulfonyl, sec-butylsulfonyl, t
tert-butylsulfonyl.

C ₂ -C ₄ in the definition of W, T ¹ or Y
Examples of the alkoxyalkyl include C ₁ -C ₃ alkoxy-methyl, C ₁ -C ₂ alkoxy-ethyl, methoxyethoxymethyl and methoxypropyl.

C ₂ in the definition of G, U ¹ , U ² or W
The alkylcarbonyl -C _4, acetyl, propionyl, butanoyl, iso- butanoyl and the like.

Examples of the C ₂ -C ₆ haloalkylcarbonyl in the definition of G include chloroacetyl, trifluoroacetyl, 3,3,3-trifluoropropionyl, pentafluoropropionyl and the like.

The C ₂ -C ₅ haloalkylcarbonyloxy in the definition of W includes chloroacetyloxy, trifluoroacetyloxy, 3,3,3-trifluoropropionyloxy, pentafluoropropionyloxy and the like.

The C ₃ -C ₇ dialkylaminocarbonyloxy in the definition of Y includes dimethylaminocarbonyloxy, diethylaminocarbonyloxy,
-Propylaminocarbonyloxy and the like.

The naphthyl in the definition of A, W and T ¹ includes 1-naphthyl and 2-naphthyl.

As the pyridyl optionally substituted by X in the definition of W, 2-pyridyl optionally substituted by X, 3-pyridyl optionally substituted by X or 3-pyridyl optionally substituted by X Preferred is 4-pyridyl, preferably 2-pyridyl optionally substituted by X or 3-pyridyl optionally substituted by X, more preferably 2-pyridyl optionally substituted by X It is.

The thienyl optionally substituted by X in the definition of W includes 2-thienyl optionally substituted by X and 3-thienyl optionally substituted by X.

-N = CT ⁷ in the definition of W, R ¹ and Y
T ⁸ means alkylideneamino, benzylideneamino, arylideneamino or cycloalkylideneamino, methylideneamino, ethylideneamino, propylideneamino, isopropylideneamino, 4-methyl-2-pentylideneamino, cyclopentylideneamino, cyclohexylidene And denamino.

The C ₁ -C ₄ monoalkylaminosulfonyl in the definition of B includes methylaminosulfonyl,
Examples include ethylaminosulfonyl, n-propylaminosulfonyl, isopropylaminosulfonyl, and n-butylaminosulfonyl.

C ₂ -C ₈ dialkylaminosulfonyl in the definition of B includes dimethylaminosulfonyl, diethylaminosulfonyl, di-n-propylaminosulfonyl, diisopropylaminosulfonyl and di-n-
Butylaminosulfonyl and the like.

The C ₂ -C ₅ monoalkylaminothiocarbonyl in the definition of B includes methylaminothiocarbonyl, ethylaminothiocarbonyl, n-propylaminothiocarbonyl, isopropylaminothiocarbonyl and n-butylaminothiocarbonyl. can give.

C ₃ -C ₉ dialkylaminothiocarbonyl in the definition of B includes dimethylaminothiocarbonyl, diethylaminothiocarbonyl, di-n-propylaminothiocarbonyl, diisopropylaminothiocarbonyl and di-n-butylaminothiocarbonyl And so on.

In the definition of B, C ₁ -C substituted with R ^b
Examples of C ₄ alkyl include phenacyl, 2-fluorophenacyl, 3-chlorophenacyl, 4-bromophenacyl, 2-methylphenacyl, 3-ethylphenacyl,
-I-propylphenacyl, 4-t-butylphenacyl and the like.

In the definition of B, a halogen atom and C
₁ -C As good phenylsulfonyl optionally substituted by one or more selected from _alkyl, 2-fluorophenyl sulfonyl, 4-fluorophenyl sulfonyl, 2
-Chlorophenylsulfonyl, 4-chlorophenylsulfonyl, 4-bromophenylsulfonyl, 2,5-dichlorophenylsulfonyl, pentafluorophenylsulfonyl, 4-methylphenylsulfonyl, 2-methylphenylsulfonyl, 4-t-butylphenylsulfonyl, 2,5 -Dimethylphenylsulfonyl, 2,4-dimethylphenylsulfonyl, 2,4,6-trimethylphenylsulfonyl, 2,4,6-tri-i-propylphenylsulfonyl and the like.

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

C ₃ -C ₉ alkoxycarbonylalkyl in the definition of B includes methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propoxycarbonylmethyl, i-propoxycarbonylmethyl, n-propoxycarbonylmethyl as straight-chain or branched alkoxycarbonylalkyl. Butoxycarbonylmethyl, i-butoxycarbonylmethyl, t-butoxycarbonylmethyl, n-hexyloxycarbonylmethyl, n-heptyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-n-butoxyethyl, 2 -Methoxycarbonylethyl, 2-ethoxycarbonylethyl,
1-methoxycarbonylpropyl, 3-ethoxycarbonylpropyl, 4-methoxycarbonylbutyl, 6-ethoxycarbonylhexyl, 1-methoxycarbonyl-1
-Methylethyl, 1-iso-propoxycarbonyl-
1-methylethyl, 1-ethoxycarbonyl-2-methylpropyl and the like.

As the alkali metal in the definition of B,
Lithium, sodium and potassium.

The alkaline earth metal in the definition of B includes magnesium, calcium, strontium or barium, preferably magnesium, calcium or barium.

As the ammonium represented by NHT ⁴ T ⁵ T ⁶ in the definition of B, ammonium , Monomethylammonium, dimethylammonium, trimethylammonium, diethylammonium, triethylammonium, diisopropylammonium, diisopropylethylammonium, hexylmethylammonium, cyclopropylmethylammonium, cyclohexylmethylammonium, allylmethylammonium, benzylmethylammonium or 4-methylcyclohexyl A 5-membered heterocyclic ring which may be ethylammonium or two of T ⁴ , T ⁵ and T ⁶ may contain an oxygen atom, a nitrogen atom or a sulfur atom together with the nitrogen atom to which each is attached; 6-membered ring, 7-membered ring or 8-membered ring ammonium and the like can be mentioned.

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

As the haloalkylsulfenyl in the definition of G, W, X, Y or Z, straight-chain or branched-chain haloalkylthio includes fluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, trifluoromethylthio, trichloromethylthio,
2,2,2-trifluoroethylthio, 1,1,2,2
-Tetrafluoroethylthio, fluoroethylthio, pentafluoroethylthio, fluoro-iso-propylthio and the like.

As the haloalkylsulfinyl in the definition of G, W, X, Y or Z, linear or branched haloalkylsulfinyl include fluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, trifluoromethylsulfinyl, Trichloromethylsulfinyl, 2,
2,2-trifluoroethylsulfinyl, 1,1,
Examples thereof include 2,2-tetrafluoroethylsulfinyl, fluoroethylsulfinyl, pentafluoroethylsulfinyl, and fluoro-iso-propylsulfinyl.

As the haloalkylsulfonyl in the definition of G, W, X, Y or Z, straight-chain or branched-chain haloalkylsulfonyl includes fluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, trifluoromethylsulfonyl, Trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, fluoroethylsulfonyl, pentafluoroethylsulfonyl and fluoro-iso-
Propylsulfonyl and the like.

The haloalkenyl in the definition of G or W includes 2-chloroethenyl, 2-bromoethenyl and 2-chloroethenyl as a C ₂ -C ₄ linear or branched haloalkenyl.
2,2-dichloroethenyl and the like.

Alkenyloxy in the definition of G, T ¹ , W or Y includes allyloxy, 2-propenyloxy, and linear or branched alkenyloxy.
-Butenyloxy, 2-methyl-2-propenyloxy and the like.

Haloalkenyloxy in the definition of G, W or Y includes 3-chloro-2-propenyloxy as linear or branched haloalkenyloxy,
3,3-dichloro-2-propenyloxy, 4-chloro-2-butenyloxy, 4,4-dichloro-3-butenyloxy, 4,4-difluoro-3-butenyloxy and the like.

Alkenylsulfenyl in the definition of G, W, X, Y or Z includes allylsulfenyl and 2-alkenylsulfenyl as linear or branched alkenylsulfenyl.
Propenylsulfenyl, 2-butenylsphenyl, 2
-Methyl-2-propenylsulfenyl and the like.

In the definition of G, W, X, Y or Z, alkenylsulfinyl includes straight-chain or branched alkenylsulfinyl, such as allylsulfinyl and 2-alkenylsulfinyl.
Propenylsulfinyl, 2-butenylsphinyl, 2
-Methyl-2-propenylsulfinyl and the like.

Alkenylsulfonyl in the definition of G, W, X, Y or Z includes allylsulfonyl, 2-propenylsulfonyl, 2-butenylsulfonyl, and 2-methyl- as straight-chain or branched alkenylsulfonyl.
2-propenylsulfonyl and the like.

The haloalkenylsulfenyl in the definition of G, W or Y includes 3-chloro-2-propenylsulfenyl, 4-chloro-2-butenylsulfenyl as a linear or branched haloalkenylsulfenyl, 3,3-dichloro-2-propenylsulfenyl,
4,4-dichloro-3-butenylsulfenyl, 4,4
-Difluoro-3-butenylsulfenyl and the like.

The haloalkenylsulfinyl in the definition of G, W or Y includes 3-chloro-2-propenylsulfinyl, 3,3-dichloro-2-propenylsulfinyl, 4-chloro as a straight-chain or branched haloalkenylsulfinyl -2-butenylsulfinyl,
4,4-dichloro-3-butenylsulfinyl, 4,4
-Difluoro-3-butenylsulfinyl and the like.

As the haloalkenylsulfonyl in the definition of G, W or Y, 3-chloro-2-propenylsulfonyl, 3,3-dichloro-2-propenylsulfonyl, 4-chloro -2-butenylsulfonyl, 4,4-dichloro-3-butenylsulfonyl, 4,4-difluoro-3-butenylsulfonyl and the like.

The haloalkynyl in the definition of G or W includes chloroethynyl, bromoethynyl, iodoethynyl, 3-chloro-1-propynyl, 3-bromo-1
-Butynyl and the like.

The alkynyloxy in the definition of G, W or Y includes 2-propynyloxy, 2-butynyloxy, 1-methyl-2-propynyloxy and the like.

The haloalkynyloxy in the definition of G, W or Y includes 3-chloro-2-propynyloxy, 3-bromo-2-propynyloxy, 3-iodo-
2-propynyloxy and the like.

The alkynylsulfenyl in the definition of G, W or Y includes 2-propynylsulfenyl,
2-butynylsulfenyl, 1-methyl-2-propynylsulfenyl and the like can be mentioned.

Alkynylsulfinyl in the definition of G, W or Y includes 2-propynylsulfinyl,
2-butynylsulfinyl, 1-methyl-2-propynylsulfinyl and the like.

The alkynylsulfonyl in the definition of G, W or Y includes 2-propynylsulfonyl, 2-
Butynylsulfonyl, 1-methyl-2-propynylsulfonyl and the like.

Examples of haloalkynylsulfenyl in the definition of G, W or Y include 3-chloro-2-propynylsulfenyl, 3-bromo-2-propynylsulfenyl, 3-iodo-2-propynylsulfenyl and the like. Can be

Examples of haloalkynylsulfinyl in the definition of G, W or Y include 3-chloro-2-propynylsulfinyl, 3-bromo-2-propynylsulfinyl, 3-iodo-2-propynylsulfinyl and the like.

The haloalkynylsulfonyl in the definition of G, W or Y includes 3-chloro-2-propynylsulfonyl, 3-bromo-2-propynylsulfonyl,
3-iodo-2-propynylsulfonyl and the like.

The alkylcarbonyloxy in the definition of G, W or Y includes acetoxy, propanoyloxy, butanoyloxy, isopropylcarbonyloxy and the like, and is selected within the range of each designated carbon number.

The benzoyl which may be substituted by X in the definition of G includes benzoyl, 2-chlorobenzoyl, 3-chlorobenzoyl, 4-chlorobenzoyl,
4-bromobenzoyl, 4-fluorobenzoyl, 3-
Methylbenzoyl, 4-methylbenzoyl, 4-tert-butylbenzoyl, 3,4-dichlorobenzoyl and the like can be mentioned.

The compound of the present invention is useful for so-called agricultural pests that infest 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. The so-called stored pests that injure stored grains and the like, and any pests such as mites, nematodes, molluscs, 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, but are not limited to, the following. 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 asters, black leafhoppers, brown planthoppers, peach aphids, cotton aphids, wheat aphids, peach aphids, legume aphids, whitefly,
Hemiptera pests such as silverleaf whitefly, pear lice, azalea hornbill, lycaenidae, scutellidae, ruby roe beetle, ruby beetle, sea turtle, bed bug, etc. Coleoptera pests such as leaf beetles, horned beetles, pine wood beetles, corn rootworms, coco elephants, granary weevil, scutellaria, and maggots, flies,
Diptera pests such as Hessian flies, sea flies, medfly, house flies, sand flies, sheep flies, cystis, flies, sheep, flies, tsetse flies, mosquitoes, Aedes aegypti, and anopheles,

Hymenopteran pests such as the wasps, pine saw wasps, and black wasps; Thrips palmi, Thrips palmi, Thrips palmi, Thrips thrips; Pests, Orthoptera pests such as Tonosa locusts, Siberian locusts, Mackerel locusts, Termite pests such as house termites, Yamato termites, and Taiwan termites, Isoptera pests such as cat fleas, human fleas, and cepopterine fleas,
Louse pests such as chicken lice, lice and lice, lice such as bovine lice, porcine lice, lice, nits Dust mites such as Dermatophagoid mites, Dermatophagoides mite, Dermatophagoides farinae such as Cyclamen mites, Dermatophagoid mites, Robin nematodes and the like.
Dermatophagoids such as honey beetle mites, Dermatophagoids such as Oxodid tick, Dermatophagoides farinae, Dermatophagoids such as Dermatophagoides, Sweet potato nematode, Kitaneko nematode, Kitanegusaresenchus,
Nematodes such as walnut and nematodes, potato cyst nematodes, and pine wood nematodes, mollusks such as snails, slugs, slugs, and mussels, and crustaceans such as paddy beetles.

The plant diseases to be controlled by the compounds of the present invention include rice blast (Pyriculari).
a oryzae), Sesame leaf blight (Cochliobo)
rus miyabeanus, Sheath blight (Rhizo)
ctonia solani, wheat powdery mildew (Erysiphe graminis f. sp.h)
ordei, f. sp. tritici), leaf spot disease (P
yrenophora graminea, net spot disease (Pyrenophora teres), red mold (Gibberella zeae), rust (Puc)
cinia striiformis, p. grami
nis, P .; recondita, P .; horde
i), snow rot (Typhula sp., Micron)
ectriella nivais), naked smut (Us)
tilago tritici, U.S.A. nuda), eye spot (Pseudocercosporella)
herpotrichoids, cloudy sickness (Rhyn)
chosporium secalis, leaf blight (S
eptria tritici), Fusarium wilt (Lept)
osphaeria nodorum, citrus black spot (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum, P. et al.
italicum), Monilia disease of apple (Schler)
otinia mali, rot (Valsam)
ali), powdery mildew (Podphaera le)
ucotricha), spot leaf spot (Alternar)
ia mali), Scab (Venturia ina)
equialis), pear scab (Venturia)
nasicola), black spot (Alternaria)
Kikuchiana, scab (Gymnospo)
rangium haraeanum),

Peach ash disease (Sclerotinia)
cinerea), scab (Cladosporium)
carpophilum), Phomopsis rot (P
hompsis sp. ), Grape downy mildew (Pla
smopara viticola, black rot (El)
sinoe ampelina, late rot (Glome)
rella singulata), powdery mildew (Un
cinula necrotor, rust (Phako)
psora ampelopsidis), oyster anthracnose (Gloeosporium kaki), leaf rot (Cercospora kaki, Mycospha)
erella nawae), downy mildew of cucumber (Pse
udoperenospora cubensis),
Anthracnose (Colletotrichum lagena)
rium), powdery mildew (Sphaerotheca)
fluginea), vine blight (Mycosphae)
rella melonis, tomato blight (Phy)
tophthora infestans, Alternaria solani, Leaf mold (Cladosporium fulvam), Eggplant brown spot (Phomopsis vexans), Powdery mildew (Erysiphe cichocoarau)
m), black spot of cruciferous vegetables (Alternaria)
japonica), vitiligo disease (Cerocospor)
ella brassicae), rust on leeks (Pu)
ccinia allii), soybean purpura (Cer)
cospora kikuchii, black rot (El)
sinoe glycines, black spot disease (Diapo)
rthe phaseolum),

[0169] Bean anthracnose (Colletotri)
chum lindemutianum, peanut black spot (Mycosphaerella pers)
onatum), brown spot (Cercospora ar)
achidicola), powdery mildew of pea (Er)
ysiphe pisi), potato summer blight (Al
ternaria solani), strawberry powdery mildew (Sphaerotheca humuli), tea net blast (Exobasidium reticul)
atum), scab (Elsinoe leeucosp)
ila), scab of tobacco (Alternaria l)
ongipes), powdery mildew (Erysiphe c)
ichoracearum, anthracnose (Colleto)
trichum tabacum, sugar beet brown spot (Cercospora beticola), rose scab (Diplocarpon roseae), powdery mildew (Sphaerotheca pannos)
a), chrysanthemum spot of chrysanthemum (Septoria chrysa)
nthemiindici, white rust (Puccin)
ia horiana), gray mold on various crops (B
otrytis cinerea), sclerotia rot of various crops (Sclerotinia sclerotioru)
m) 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 Mite and Lice at low concentrations. Can be controlled. On the other hand, the compounds of the present invention include extremely useful compounds having little adverse effect on mammals, fish, crustaceans and beneficial insects.

The compound of the present invention can be synthesized by the following method (Scheme 1). Scheme 1

[0172]

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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, C ₁ -C ₄ alkoxy, phenoxy, 1-pyrazolyl or 1-imidazolyl, etc., and L ′ is a halogen atom, C ₁ -C ₄ alkylsulfonyloxy, benzenesulfonyloxy, toluenesulfonyloxy, etc. L ″ represents a halogen atom, alky
l is alkyl, preferably C ₁ -C ₄ alkyl. The method A in (Scheme 1) is a method for preparing an acetonitrile derivative represented by the general formula (3) and an acid chloride or ester represented by the general formula (4), or an acid anhydride represented by the general formula (5). A method for synthesizing the compound (1 ′) of the present invention by reacting a compound with the compound will be described. Further, the compound (1 ') of the present invention is an alkyl halide, alkyl sulfonate, trimethylsilyl halide, sulfonyl chloride, sulfamoyl chloride, thiocarbamoyl chloride, acid chloride or ester represented by the general formula (8) Can be converted to the compound (1) of the present invention by reacting with the compound. At this time, the present 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 be synthesized also by the 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 by a nitrogen atom, it can be synthesized also by the 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). In some cases, the compound represented by the general formula (9) can be synthesized by reacting the acetonitrile derivative represented by the general formula (3) shown by the method A 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, Et: ethyl, Pr: propyl, Bu: butyl, Pen: pentyl, Hex: hexyl, Hep: heptyl, Oct: octyl, Non: nonyl, Dec: decyl, Ph: phenyl, n: normal , I: iso, sec: secondary, t: tertiary,
c: cyclo,

[0183]

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[0184]

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[0185]

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[0186]

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[0187]

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[0188]

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[0189]

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[Table 1]

[0191]

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[0192]

[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 1-Me B2 Me Me nPr R3 H 1-Me B8 Me Me Me R3 H 1-Me B8 Me Cl Me R3 H 1-Me B8 Cl Cl Me R3 H 1-Me B8 CF ₃ Cl Me 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 R6 HH B8 Me Me Me R7 HH B6 CF ₃ H sBu R7 H 5-Me B7 CF ₃ Cl Me R7 H 5-Me B7 Me Cl Me R7 H 5-Me B7 Cl Cl Me 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 R12 Me H B7 Cl Cl 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 B 22 Me Cl Me 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 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 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 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 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 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 R40 HH B7 Me Cl Me R41 H 3-Me H Me Cl Me R42 H 6-Me ₂ NH H Cl Cl Me R42 HHH Me Cl Me ―――――――――――――――― ―――――――――――――――――――

[Table 2]

[0194]

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[0195]

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[0196]

[Table 2] ――――――――――――――――――――――――――――――――― 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 1-Me nHexOCO H Br Et R3 H 1-Me B8 Me Me Me R4 H 2,4-Me ₂ Nicotinoyl Cl Me Me R5 H 2-Me-5-MeCONH Pucoinoyl Cl Me nBu R6 H 5 -EtO Isonicotinoyl Me H Me R7 H 4-Cl-5-Me H Me MeS Me R7 H 5-Me B7 Me Me 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 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 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 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 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 Nicotinol MeMe Me R36 HH 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 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]

[0198]

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[0199]

[Table 3] ――――――――――――――――――――――――――――――――――― 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 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-C l 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 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 R36 HH B15 Me Me R36 HH B15 CF ₃ Me R36 HH B15 Me Cl R36 HH Nicotinoyl Cl Cl R36 HH Picolineo 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 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]

[0201]

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[0202]

[Table 4] ―――――――――――――――――――――――――――――――――― 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 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 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 R3 3 HH B7 nPrO H R33 HH B7 CHF ₂ OH R33 HH B7 CBrF ₂ OH 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 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 NHCOMe H R36 HHH CN H R H R36 HHH MeO H R36 HHH EtO H R36 HHH nPrO H R36 HHH CHF ₂ OH R36 HHH CBrF ₂ OH 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 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 ――――――――― ――――――――――――――――――――――――――

[Table 5]

[0204]

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[0205]

[Table 5] ――――――――――――――――――――――――――――――――― RR ¹ GB A ――――――― ―――――――――――――――――――――――――――― R3 H 1-Me B7 A1 R7 HH B7 A1 R10 HH B7 A1 R12 HH B7 A1 R20 H 1 -Me B7 A1 R22 H 5-Me B7 A1 R24 H 5-Me B7 A1 R36 H 3-Me B7 A1 R36 H 3-Et B7 A1 R3 H 1-Me B7 A2 R7 HH B7 A2 R10 HH B7 A2 R12 HH B7 A2 R20 H 1-Me B7 A2 R22 H 5-Me B7 A2 R24 H 5-Me B7 A2 R36 H 3-Me B7 A2 R36 H 3-Et B7 A2 R3 H 1-Me B7 A3 R7 HH B7 A3 R10 HH B7 A3 R12 HH B7 A3 R20 H 1-Me B7 A3 R22 H 5-Me B7 A3 R24 H 5-Me B7 A3 R36 H 3-Me B7 A3 R36 H 3-Et B7 A3 R3 H 1-Me B7 A4 R7 HH B7 A4 R10 HH B7 A4 R12 HH B7 A4 R20 H 1-Me B7 A4 R22 H 5-Me B7 A4 R24 H 5-Me B7 A4 R36 H 3-Me B7 A4 R36 H 3-Et B7 A4 R33 HH B7 A5 R36 HH B7 A5 R33 HH B7 A6 R36 HH B7 A6 R33 HH B7 A7 R36 HH B7 A7 R33 HH B7 A8 R36 HH B7 A8 R33 HH B7 A9 R36 HH B7 A9 R1 HH B7 A10 R2 HH B7 A10 R3 H1-Me B7 A10 R4 HH B7 A10 R5 HH B7 A10 R6 HH B7 A10 R7 HH B7 A10 R8 HH B7 A10 R9 HH B7 A10 R10 HH B7 A10 R11 HH B7 A10 R12 HH B7 A10 R13 HH B7 A10 R14 HH B7 A10 R15 HH B7 A10 R16 HH B7 A10 R17 HH B7 A10 R18 H19 B10 HH B7 A10 R20 H 1-Me B7 A10 R21 HH B7 A10 R22 H 5-Me B7 A10 R23 HH B7 A10 R24 H 5-Me B7 A10 R25 HH B7 A10 R26 HH B7 A10 R27 HH B7 A10 R28 HH B7 A10 R29 H 4-Me B7 A10 R30 H 5-Me B7 A10 R31 H 1-Me B7 A10 R32 H 1-Me B7 A10 R34 HH B7 A10 R35 HH B7 A10 R36 H 3-Me B7 A10 R36 H 3-Et B7 A10 R37 HH B7 A10 R38 HH B7 A10 R39 HH B7 A10 R40 HH B7 A10 R41 HH B7 A10 R42 HH B7 A10 R3 H 1-Me B7 A11 R7 HH B7 A11 R10 HH B7 A11 R12 HH B7 A11 R20 H 1-Me B7 A11 R22 H 5-Me B7 A11 R24 H 5-Me B7 A11 R36 H 3-Me B7 A11 R36 H 3-Et B7 A11 R3 H 1-Me B7 A12 R7 HH B7 A12 R10 HH B7 A12 R12 HH B7 A12 R20 H 1-Me B7 A12 R22 H 5-Me B7 A12 R24 H 5-Me B7 A12 R36 H 3-Me B7 A12 R36 H 3-Et B7 A12 R33 HH B7 A13 R36 HH B7 A13 R33 HH B7 A14 R36 HH B7 A14 R33 HH B7 A15 R36 HH B7 A15 R33 HH B7 A16 R36 HH B7 A16 R33 HH B7 A17 R36 HH B7 A17 R33 HH B7 A18 R36 HH B 7 A18 R33 HH B7 A19 R36 HH B7 A19 R33 HH B7 A20 R36 HH B7 A20 R12 HH B7 A21 R36 H 3-Me B7 A21 R33 HH B7 A22 R36 HH B7 A22 R33 HH B7 A23 R36 HH B7 A23 R3 H 1-Me B7 A24 R7 HH B7 A24 R10 HH B7 A24 R12 HH B7 A24 R20 H 1-Me B7 A24 R22 H 5-Me B7 A24 R24 H 5-Me B7 A24 R36 H3-Me B7 A24 R36 H 3-Et B7 A24 R3 H 1-Me B7 A25 R7 HH B7 A25 R10 HH B7 A25 R12 HH B7 A25 R20 H 1-Me B7 A25 R22 H 5-Me B7 A25 R24 H 5-Me B7 A25 R36 H3-Me B7 A25 R36 H 3- Et B7 A25 R33 HH B7 A26 R36 HH B7 A26 R33 Me H B7 A27 R36 H 3-Me B7 A27 R12 HH B7 A28 R36 H 3-Me B7 A28 R33 HH B7 A29 R36 HH B7 A29 R33 HH B7 A30 R36 HH B7 A30 R3 H 1-Me B7 A31 R7 HH B7 A31 R10 HH B7 A31 R12 HH B7 A31 R20 H 1-Me B7 A31 R22 H 5-Me B7 A31 R24 H 5-Me B7 A31 R36 H 3-Me B7 A31 R36 H 3 -Et B7 A31 R3 H 1-Me B7 A32 R7 HH B7 A32 R10 HH B7 A32 R12 HH B7 A32 R20 H 1-Me B7 A32 R22 H 5-Me B7 A32 R24 H 5-Me B7 A32 R36 H 3-Me B7 A32 R36 H 3-Et B7 A32 R33 HH B8 A33 R36 HH B7 A33 R33 HH B8 A34 R36 HH B7 A34 R33 HH B7 A35 R36 HH B7 A35 R33 HH B7 A36 R36 HH B7 A36 R33 HH B7 A37 R36 HH B7 A37 R33 HH B7 A38 R36 HH B7 A38 R33 HH B7 A39 R36 HH B7 A39 R33 HH B7 A40 R36 HH B7 A40 R33 HH B7 A41 R36 HH B7 A41 R33 HH B7 A42 R36 R33 HH B7 A43 R36 HH B7 A43 R33 HH B7 A44 R36 HH B7 A44 R3 H 1-Me B7 A45 R7 HH B7 A45 R10 HH B7 A45 R12 HH B7 A45 R20 H 1-Me B7 A45 R22 H 5-Me B7 A45 R24 H 5-Me B7 A45 R36 H 3-Me B7 A45 R36 H 3-Et B7 A45 R33 HH B7 A46 R36 HH B7 A46 R33 HH B7 A47 R36 HH B7 A47 R33 HH B7 A48 R36 HH B7 A48 R33 HH B7 A49 R36 HH B7 A49 R33 HH B7 A50 R36 HH B7 A50 R33 HH B7 A51 R36 HH B7 A51 R33 HH B7 A52 R36 HH B7 A52 R33 HH B7 A53 R36 HH B7 A53 R33 HH B7 A54 R36 HH B7 A54 R33 HH B7 A55 R36 H33 A55 HH B7 A56 R36 HH B7 A56 R33 HH B7 A57 R36 HH B7 A57 ―――――――――――――――――――――――――――――――――――

In applying the compound of the present invention, it is usually mixed with a suitable solid carrier or liquid carrier, and if desired, 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.

Examples of the liquid carrier include alcohols such as ethylene glycol, propylene glycol and isopropanol; aromatic hydrocarbons such as xylene, alkylbenzene and alkylnaphthalene; ethers such as butyl cellosolve; ketones such as cyclohexanone;
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.

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

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 herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators may be used as needed when formulating or spraying. It may be applied in combination with an agent, a synergist, a fertilizer, a soil conditioner and the like.

[0213] In particular, by applying the mixture with other pesticides 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 agent, 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 agrochemical 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, and the like, but is generally 0.000 per hectare (ha) as an active ingredient.
About 5 to 50 kg is appropriate.

[0215] Formulation examples of preparations using the compound of the present invention are shown below. However, the composition examples of the present invention are not limited only 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 an anti-decomposition agent. .

[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.

[Solvent] 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.

Next, more specific examples of the formulation of the pesticidal composition containing the compound of the present invention as an active ingredient are shown, but the present invention is not limited to these.

[0224] 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 The present compound No. 1 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, mixing and kneading, granulating with an extrusion granulator, and drying. Granular wettable powder.

[Formulation 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.

[0232]

[Examples] Synthesis 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] 3- (4-chloro-1,3-
Dimethylpyrazol-5-yl) -3-hydroxy-2
Synthesis of-(2-pyrazinylthiazol-4-yl) acrylonitrile (Compound No. 11) 4-cyanomethyl-2-pyrazinylthiazole 2.00
g, and 2.44 g of 4-chloro-1,3-dimethyl-5- (1-pyrazolylcarbonyl) pyrazole were added to 50 ml of dry tetrahydrofuran, and potassium was stirred under ice cooling.
2.22 g of t-butoxide were added. 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.

[Synthesis Example 2] 3- (4-chloro-1,3-
Synthesis of dimethylpyrazol-5-yl) -3-pivaloyloxy-2- (2-pyrazinylthiazol-4-yl) acrylonitrile (Compound No. 12) 0.1 g of 60% sodium hydride was washed with n-hexane. And 20 ml of dry tetrahydrofuran. 3- (4-chloro-1,3-dimethylpyrazole) under ice-cooling and stirring
-3-Hydroxy-2- (2-pyrazinylthiazole-
After slowly adding 0.60 g of 4-yl) acrylonitrile, the mixture was stirred at room temperature for 1 hour. 0.25 g of pivaloyl chloride 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: 178-17
9 ° C.

The structures and melting points of the compounds of the present invention synthesized according to the above scheme or the above synthesis examples are shown in Tables 6 to 9, but those not particularly described are mixtures of E-form and Z-form. The abbreviations in the table have the same meaning as described above. [Table 6]

[0236]

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[0237]

[Table 6] ――――――――――――――――――――――――――――――――――― No. RR ¹ GB A Melting point (℃), Isomer ratio ――――――――――――――――――――――――――――――――― 1 R16 HH B7 A10 129.5-131, E-form or Z form 2 R16 HH B7 A10 Resin, E form / Z form mixture 3 R16 HHH A10 152-153.5 4 R36 HHH A2 230-231 5 R36 HH B7 A2 124-128, E form / Z form mixture 6 R36 HHH A3 209 -210 7 R36 HH B7 A3 180-181.5, E-form / Z-form mixture 8 R36 HHH A4 218-221 9 R36 HH B7 A4 194-195.5, E-form or Z-form 10 R36 HH B36 A10 184-185, E-form or Z form 11 R36 HHH A11 228.5-230 12 R36 HH B7 A11 178-179, E form or Z form 13 R36 HH B7 A24 Resin, 1/1 14 R36 HHH A25 235-237 15 R36 HH B7 A25 125-128, E / Z mixture 16 R36 HH B7 A25 157-157.5, E or Z 17 R36 HHH A27 214-215 18 R36 HH B7 A27 149-150,87 / 6 19 R36 HHH A31 273-274.5 20 R36 HH B7 A31 157-1 59 、 E- / Z-mixture ―――――――――――――――――――――――――――――――――――

[Table 7]

[0239]

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[0240]

[Table 7] ――――――――――――――――――――――――――――――――――― No. RR ¹ GB A Melting point (℃), Isomer ratio ――――――――――――――――――――――――――――――――― 21 R12 HHH A2 224.5-226 22 R12 HH B7 A2 70-72, E or Z form 23 R12 HHH A10 128.5-131 24 R12 HH B7 A10 211-213, E or Z form 25 R17 H 1-Me-5-Cl H A2 238-243 ――――― ――――――――――――――――――――――――――――――

[Table 8]

[0242]

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[0243]

[Table 8] ――――――――――――――――――――――――――――――――― No. RR ¹ GB A Melting point (℃), Isomer ratio ――――――――――――――――――――――――――――――――― 26 R1 HHH A11 Resin-like 27 R1 H 5-Me H A11 Resin 28 R1 HH B7 A11 Resin 29 R1 H 5-Me B7 A11 Resin 30 R3 H 1-Me H A10 Resin 31 R3 H 1-Me B7 A10 Resin, E-form or Z-form 32 R3 H 1-Me B7 A10 Resin, 1/2 33 R7 H 5-Me B7 A2 Resin, E-form or Z-form 34 R7 H 5-Me B7 A10 Resin-form, E-form or Z-form 35 R10 H 2,4- diMe H A11 Resin 36 R10 H 2,4-diMe B7 A11 Resin 37 R12 HHH A1 127-128 38 R12 HH B7 A1 172-173, E or Z 39 R12 HHH A2 165.8-169.3 40 R12 HH B7 A2 Resin 41 R12 HHH A3 133-134 42 R12 HH B7 A3 124-125, E or Z 43 R12 HHH A10 Resin 44 R12 HH B7 A10 127-128.3, E or Z 45 R12 HHH A25 140-141 46 R12 HH B7 A25 103-104, E-form or Z-form 47 R12 HH B7 A25 resin, Z-form or E-form 48 R12 HH B7 A32 Resin-form, E-form or Z-form 49 R12 HHH A45 188-189 50 R12 HH B7 A45 101-102, E-form or Z form 51 R12 HHH A48 139-141 52 R12 HH B7 A48 Resin, E form or Z form 53 R20 H 1-Me H A3 141-143 54 R20 H 1-Me B7 A3 119-122, E form or Z form 55 R20 H 1-Me H A10 236-237 56 R20 H 1-Me B7 A10 Resin, E / Z mixture 57 R20 H 1-Me H A25 242-243 58 R20 H 1-Me B7 A25 119-120 , E-form or Z-form 59 R33 HH B7 A10 resin, E-form or Z-form 60 R34 HH B7 A10 resin-like, 1/2 61 R36 HHH A4 177.5-180 62 R36 HH B7 A4 145-146, E-form or Z Form 63 R36 HHH A10 Resin form 64 R36 HH Me A10 Resin form, E form or Z form 65 R36 HHC (O) (3-polysilyl) A10 166-172, E form or Z form 66 R36 HH B3 A10 Resin form, E Form or Z form 67 R36 HH B6 A10 135-151, 2/1 68 R36 HH B7 A10 Resin 69 R36 HH B34 A10 Resin, 2/1 70 R36 HH B36 A10 147 -151, E-form or Z-form 71 R36 H 3-Et H A10 resin, 72 R36 H 3-Et B7 A10 115.2-117.1, E-form or Z-form 73 R36 H 3-Et B7 A10 resin, 1/9 74 R36 H3-Me B7 A2 Resin, E-form or Z-form 75 R36 H3-Me B7 A10 Resin-like, 1/1 76 R36 HHH A11 294-296 77 R36 HH B7 A11 130-131.5, E-form or Z Form 78 R36 HH B7 A25 97-99, E-form / Z-form mixture 79 R36 HH B7 A25 133.5-134, E-form or Z-form 80 R36 HHH A27 261-265 ――――――――――――― ――――――――――――――――――――――

[Table 9]

[0245]

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[0246]

[Table 9] ――――――――――――――――――――――――――――――――― No. RR ¹ GB A Melting point (℃), Isomer ratio ――――――――――――――――――――――――――――――――― 81 R12 Me HH A2 167.1-169.3 82 R12 Me H B7 A2 Resin 83 R12 Me HH A10 166.3-167.9 84 R12 Me H B7 A10 Resin 85 R12 HH B7 A10 Resin ――――――――――――――――――――――― ――――――――――――

[Table 10]

[0248]

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[0249]

[Table 10] ――――――――――――――――――――――――――――――――――― No. RR ¹ GB A Melting point (℃), Isomer ratio ――――――――――――――――――――――――――――――――― 86 R3 H 1-Me H A10 158.2-160.3 87 R3 H 1-Me B7 A10 Resin, 9/1 88 R3 H 1-Me B7 A10 Resin, 1/9 ――――――――――――――――――――――― ――――――――――――

Next, the usefulness of the compound of the present invention as a pesticide 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. It was prepared into a drug solution having a concentration of 500 ppm.

This chemical solution was sprayed on rice foliage planted in a 1/2000 are pot in a sufficient amount. After air-drying, the cylinder was set up, and the second instar larva of brown planthopper was placed in a pot for 1
0 insects were released, covered, and stored in a constant temperature room. The survey was conducted after 6 days, and the mortality was calculated from the following formula. The test was performed in two sections.

[0253]

## EQU1 ## Insect rate (%) = [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, 4, 5,
6, 10, 11, 12, 13, 18, 20, 28, 3
7, 38, 39, 40, 41, 42, 43, 44, 4
5, 46, 47, 48, 49, 50, 63, 65, 6
6, 67, 68, 69, 70, 75, 76, 77, 8
2, 84, 85.

Test Example 2 Insecticidal test against black leafhopper Rice foliage 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 exhibit resistance to organophosphorus pesticides. Release the adult leafhopper, shown below, cover it with a perforated lid and store it in a constant temperature room at 25 ° C.
The number of dead insects after the day 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, 3, 4,
5, 6, 10, 11, 12, 13, 17, 18, 19,
20, 21, 22, 23, 28, 29, 30, 31, 3,
2, 37, 38, 39, 40, 41, 42, 43, 4
4, 45, 46, 47, 48, 49, 50, 52, 6
1, 62, 63, 65, 66, 67, 68, 69, 7
0, 71, 74, 75, 76, 77, 81, 82, 8
3, 84, 85.

[Test Example 3] Insecticidal test against peach aphid A 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.

[0259]

## EQU2 ## Insect rate (%) = [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, 3, 4,
5, 6, 7, 8, 9, 10, 11, 12, 13, 14,
15, 16, 17, 18, 19, 20, 21, 22, 2,
3, 24, 26, 27, 28, 29, 30, 31, 3,
2, 33, 34, 35, 36, 37, 38, 39, 4
0, 41, 42, 43, 44, 45, 46, 47, 4
8, 49, 50, 51, 52, 54, 60, 61, 6
2, 63, 64, 65, 66, 67, 68, 69, 7
0, 71, 72, 73, 74, 75, 76, 77, 7
8, 79, 80, 81, 82, 83, 84, 85.

Test Example 4 Contact Insecticidal Test against P. conifer Perilla leaves are immersed in a 500 ppm aqueous emulsion of the compound of the present invention for about 10 seconds, air-dried and placed in a petri dish. Ten pets were released per petri dish, 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, 3, 4,
5, 6, 7, 8, 9, 10, 11, 12, 13, 14,
15, 16, 17, 18, 19, 20, 26, 30, 3,
1, 37, 38, 39, 40, 41, 42, 43, 4
4, 45, 46, 47, 48, 49, 50, 61, 6
2, 63, 65, 66, 67, 68, 69, 70, 8
1, 82, 83, 84, 85.

[Test Example 5] Insecticidal test against rice beetle 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. The cucumber leaf was immersed in this solution for about 10 seconds, air-dried, and placed in a petri dish.
Zero animals were released, covered and housed in a thermostat 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 a two-section system.

As a result, the following compounds exhibited 100% mortality.

The compound of the present invention no. 1, 2, 4, 5,
6, 8, 9, 10, 11, 12, 13, 14, 15, 1
6, 17, 18, 19, 38, 39, 41, 42, 4
3, 44, 45, 46, 47, 49, 50, 67, 7
0, 76, 77, 78, 79, 80.

Test Example 6 Test of Acaricidal Activity against Spider Mite A kidney bean was cut into a circular shape 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, 2, 3, 4,
5, 6, 7, 8, 10, 12, 13, 14, 15, 1
6, 18, 26, 27, 28, 29, 31, 32, 3
3, 34, 35, 36, 38, 39, 40, 42, 4
3, 44, 46, 47, 50, 52, 54, 56, 5
8, 61, 62, 63, 65, 66, 67, 68, 6
9, 70, 72, 73, 75, 76, 77, 81, 8
2, 83, 84, 85.

[0269]

As a result of the long-term use of insecticides and fungicides, pests have recently gained resistance, making it difficult to control 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. ⁷ Identification symbol FI Theme coat ゛ (Reference) C07D 405/14 C07D 405/14 413/14 413/14 417/14 417/14 (72) Inventor Hideki Ueno 722-1, Tsuboi-cho, Funabashi-shi, Chiba Nissan Chemical Industry Co., Ltd. Central Research Laboratory (72) Inventor Yoshiyuki Kusuoka 722-1, Tsuboi-cho, Funabashi-shi, Chiba Pref. Nissan Chemical Industry Co., Ltd. Central Research Laboratory (72) Inventor Yoshihide Masawa 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 Nissan Chemical Industry Co., Ltd.Bioscience Research Laboratory (72) Inventor Yoichi Inoue Saitama 1470 Shiraoka, Shiraoka-cho, Minami-Saitama-gun, Niigata Prefecture Nissan Chemical Industry Co., Ltd.Biological Science Research Laboratory (72) Inventor Norihiko Mimori Shiraoka-cho, Minami-Saitama-gun, Saitama Shirooka 1470 Nissan Chemical Industry Co., Ltd.Biological Science Research Institute (72) Inventor Takii Shinto 1470 Shirooka Town, Shirooka-cho, Minamisaitama-gun, Saitama Prefecture Nissan Chemical Industry Co., Ltd.Biological Science Research Institute (72) Inventor Toshinori Ito 1470 Shiraoka Okamachi Nissan Chemical Industry Co., Ltd. Biological Science Laboratory F-term (reference) 4C063 AA03 BB05 CC04 CC23 CC29 CC34 CC51 CC62 CC75 DD22 DD34 DD62 EE03 4H011 AA01 AB01 AC01 AC04 BA05 BB09 BB10 BC01 BC18 DA02 DA13 DA15 DA16 DG05

Claims (5)

[Claims] (1) Formula (1):Wherein Q is R and (R¹) Thiazolyl substituted with n, or
Or R and (R¹A) pyrazolyl substituted with n
A is phenyl optionally 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, pyridyl, pyrimidinyl,
Pyrazinyl, pyridazinyl, 1,3,5-triazini
1,2,4-triazinyl, indazolyl, benzo
Oxazolyl, quinolinyl, isoquinolinyl, quinoxa
Linyl, phthalazinyl, cinnolinyl or quinazolini
It is. 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, benzoxazolyl
Quinolinyl, isoquinolinyl, quinoxalinyl,
Tarazinyl, cinnolinyl or quinazolinyl
You. ) And R¹Is halogen, C₁~ C_TenAlkyl, C₁~ C_FiveArco
Xycarbonyl, NO _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 bonded at the substitution position
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 alkylene, wherein G is halogen, C₁~ 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
Chloropropyl, Rc and halogen-substituted C_Three~
C_FourCycloalkyl, R^dAnd C₁~ C_FourSubstitute with alkyl
Cyclopropyl, R^aC substituted with_Two~ C_FourAl
Kenil, C₁~ C₁₂Alkoxy, C₁~ C_FourHaloalkoki
Si, C_Two~ C_FiveAlkenyloxy, C₁~ C_ThreeAlkyl
C which may be replaced_Three~ C₆Cycloalkoxy, benzyl
Luoxy, C_Two~ C_FiveAlkoxycarbonyl, -NU
¹U^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, pyridyl, pirimi
Dinyl, pyrazinyl, pyridazinyl, 1,3,5-tri
Selected from azinyl and 1,2,4-triazinyl
You. ) 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 alkyl
May be C_Three~ C₆With cycloalkyl or benzyl
Is or T^Four, T^FiveAnd T⁶Two of them
The oxygen atom and the nitrogen atom together with the nitrogen atom
5- to 8-membered ring optionally containing a substituent 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 by one or more kinds, and Rc is 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 agricultural chemical comprising at least one acrylonitrile compound according to claim 1 as an active ingredient.