JP2002114784A - Isoxazole derivative and controller against noxious organism - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new agrochemical, especially an insecticide. SOLUTION: This isoxazole derivative is represented by formula (Q is a thiazolyl substituted with a specific group or a pyrazolyl substituted with a specific group; A is a phenyl which may be substituted with a specific group, a naphthyl which may be substituted with a specific group or a specific heterocyclic group which may be substituted with a specific group). This agrochemical comprises the isoxazole derivative.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

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

[0002]

2. Description of the Related Art Some isoxazole derivatives are disclosed in International Patent Application Publication (WO 99/02507).
There are disclosures as pesticides.

[0003]

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

[0004]

Means for Solving the Problems In order to solve the above problems, the present inventors have demonstrated excellent pest control activity at a low dose and against non-target organisms such as mammals, fish and beneficial insects. As a result of continuing research to develop a pesticide having almost no adverse effects, the present inventors have found that the following compounds have high safety and excellent pesticidal activity and completed the present invention. That is, the present invention is a compound described in the following [1] to [4] (hereinafter referred to as the present compound) and an agricultural chemical containing the compound as an active ingredient.

[1] Equation (1):

[0006]

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[0007] wherein, Q is a pyrazolyl substituted with R and (R ¹⁾ thiazolyl substituted with a _n or R and (R ¹⁾ _n,, A is optionally 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, 1,2,3-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 R is a heterocyclic group optionally substituted with G (provided that this heterocyclic group is 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, 1,2,3-
Thiadiazolyl, 1,2,3-triazolyl, 1,2,2
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. ) Or

[0008]

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And R¹Is halogen, C₁~ C_TenAl
Kill, C₁~ C_FiveAlkoxycarbonyl, NO _Two, CN,
-NU¹U^TwoOr -N = CT⁷T⁸And R^TwoIs H,
C₁~ C_TenAlkyl, 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, C_Two~ C_FourAlkoxyalkyl,
CH_ThreeSCH_Two, CH_ThreeOC_TwoH_FourOCH_Two, R^aIs replaced by
C₁~ C_FourAlkyl, R^bC substituted with₁~ C_FourArchi
Le, R^aC substituted with_Two~ C_FourAlkenyl, tetrahydride
Lopiranyl, (CH_Three)_ThreeSi, C₁~ C_FourAlkylsulfo
Nil, halogen or C₁~ C_FourSubstituted with alkyl
Optionally phenylsulfonyl, -SO_TwoCF_Three, C₁~
C_FourMonoalkylaminosulfonyl, C_Two~ C₈Dialki
Luminosulfonyl, phenylaminosulfonyl, Z
Optionally substituted pyrazolyl, substituted with Z
Imidazolyl, thiazo optionally substituted by Z
Ryl, phenyl optionally substituted with Z, substituted with Z
Pyridyl which may be optionally substituted
Limidinyl, pyrazinyl optionally substituted with Z, C
_Two~ C_FiveCyanoalkyl, C_Three~ C₉Alkoxycarbonyl
Alkyl, -C (= O) T¹, -C (= S) T¹, -P
(= O) T^TwoT^Three, -P (= S) T^TwoT^Three, Alkali metal source
Element, alkaline earth metal atom or NHT^FourT^FiveT⁶In
R^ThreeIs H, halogen, C₁~ C_TenAlkyl, C_Two~
C₆Alkenyl, 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~ C₆Haloalkoxy, C_Two~ C
₆Haloalkenyloxy, C_Two~ C₆Haloalkynyloxy
Si, C_Two~ C_FourAlkoxyalkyl, R^aC substituted with₁
~ C_FourAlkyl, R^bC substituted with₁~ C_FourAlkyl, R
^aC substituted with_Two~ C_FourAlkenyl, (CH_Three)_ThreeSi,
C₁~ C_FourAlkylsulfenyl, C ₁~ C_FourAlkylsul
Finil, C₁~ C_FourAlkylsulfonyl, halogen if
Kuha C₁~ C_FourPhenyl optionally substituted with alkyl
Sulfonyl, -SO_TwoCF_Three, C_Two~ C_FiveCyanoalkyl,
C_Three~ C₉Alkoxycarbonylalkyl, CN, -NU
¹U^Two, Phenoxy, phenylamino, -C (= O)
T¹, -C (= S) T¹, Morpholinyl, piperidyl, Z
Optionally substituted with pyrazolyl, substituted with Z
Optionally imidazolyl, thia optionally substituted by Z
Zolyl, phenyl optionally substituted with Z, substituted with Z
Pyridyl, which may be substituted by Z
Pyrazinyl or pyrazini optionally substituted by Z
N is an integer of 0 or 1, W is halo
Gen, C₁~ C_TenAlkyl, R^aC substituted with₁~ C_FourA
Luquil, C _Two~ C₆Alkenyl, C_Two~ C₆Alkynyl,
C₁~ C₆Haloalkyl, C_Two~ C₆Haloalkenyl, C_Two
~ C₆Haloalkynyl, C_Three~ C₆Halocycloalkyl,
C₁~ C_ThreeC optionally substituted with alkyl_Three~ C₆Shiku
Lower alkyl, C₁~ C₆Alkoxy, C_Two~ C₆Alkenyl
Oxy, C_Two~ C₆Alkynyloxy, C₁~ C_FourHaloal
Coxy, C_Two~ C₆Haloalkenyloxy, C_Two~ C₆Halo
Alkynyloxy, C ₁~ C_FourAlkylsulfenyl, C
₁~ C_FourAlkylsulfinyl, C₁~ C_FourAlkylsulfo
Nil, C_Two~ C₆Alkenylsulfenyl, C_Two~ C₆Al
Kenylsulfinyl, C_Two~ C₆Alkenylsulfonyl,
C_Two~ C₆Alkynylsulfenyl, C_Two~ C₆Alkini
Rusulfinyl, C_Two~ C₆Alkynylsulfonyl, C₁
~ C_FourHaloalkylsulfenyl, C₁~ C_FourHaloalk
Rusulfinyl, C₁~ C_FourHaloalkylsulfonyl, C
_Two~ C₆Haloalkenylsulfenyl, C_Two~ C₆Haloal
Kenylsulfinyl, C_Two~ C₆Haloalkenylsulfoni
Le, C_Two~ C₆Haloalkynylsulfenyl, C_Two~ C₆C
Loalkynylsulfinyl, C_Two~ C₆Haloalkynyls
Ruphonyl, NO_Two, CN, -NU¹U^Two, Phenoxy, O
H, naphthyl, C_Two~ C₇Alkoxycarbonyl, C_Two~
C_FourAlkoxyalkyl, C_Two~ C_FourAlkyl carboni
Le, C_Two~ C_FiveAlkylcarbonyloxy, C_Two~ C_FiveHalo
Alkylcarbonyloxy, optionally substituted with X
Benzoyl, phenyl optionally substituted with X,
Optionally substituted pyridyl, optionally substituted with X
Good thienyl and -N = CT⁷T⁸Arbitrarily selected from
One to four substituents, or at adjacent substitution positions
5- to 8-membered ring formed by an attached alkylene
And Y is halogen, C₁~ C_TenAlkyl, C₁~ C
₆Haloalkyl, C₁~ C₆Alkoxy, C_Two~ C₆Arche
Nyloxy, C_Two~ C₆Alkynyloxy, C₁~ C_FourHalo
Alkoxy, C_Two~ C₆Haloalkenyloxy, C_Two~ C₆
Haloalkynyloxy, C₁~ C_FourAlkylsulfeni
Le, C₁~ C_FourAlkylsulfinyl, C₁~ C_FourAlkyl
Sulfonyl, C_Two~ C₆Alkenylsulfenyl, C_Two~
C₆Alkenylsulfinyl, C_Two~ C₆Alkenyl sulf
Honyl, C_Two~ C₆Alkynylsulfenyl, C _Two~ C₆A
Ruquinylsulfinyl, 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. ) Is optional
1 to 4 substituents selected for or adjacent substituents
5 to 5 formed by an alkylene attached at a position
An 8-membered ring, wherein G is halogen, C₁~ C₆Alkyl, C
₁~ C_FourHaloalkyl, C₁~ C_FourAlkoxy, C₁~ C_FourC
Lower alkoxy, C₁~ C_FourAlkylsulfenyl, C₁~
C_FourAlkylsulfinyl, C₁~ C_FourAlkylsulfoni
Le, C₁~ C_FourHaloalkylsulfenyl, C₁~ C_FourHalo
Alkylsulfinyl, C₁~ C_FourHaloalkylsulfoni
Le, 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 of¹Is C₁~ C₂₀Alkyl, C_Two~ C₆
Alkenyl, C₁~ C₆Haloalkyl, C _Two~ C_FiveAlkoki
Sialkyl, C_Three~ C₆Halocycloalkyl, R^aReplace with
Done C₁~ C_FourAlkyl, C₁~ C_ThreeSubstituted with alkyl
May be C_Three~ C₆Cycloalkyl, R^aIs replaced by
C_Three~ C₆Cycloalkyl, R^aAnd C₁~ C_FourArchi
With cyclopropyl, Rc and halogen substituted with
Replaced C_Three~ C_FourCycloalkyl, R^dAnd C₁~ C
_FourCyclopropyl substituted with alkyl, R^aIs replaced by
C_Two~ C_FourAlkenyl, C₁~ C₁₂Alkoxy, C₁~ C
_FourHaloalkoxy, C_Two~ C_FiveAlkenyloxy, C₁~ C
_ThreeC optionally substituted with alkyl_Three~ C₆Cycloal
Coxy, benzyloxy, C_Two~ C_FiveAlkoxycarboni
, -NU¹U^Two, Phenylamino, substituted with Z
Phenyl, phenoxy optionally substituted with Z
Phenylthio optionally substituted with Z, substituted with Z
Optionally substituted with naphthyl or Z
Good 5- or 6-membered heterocyclic group (however, these heterocyclic
Groups are thienyl, furyl, pyrrolyl, oxazolyl, iso
Xazolyl, thiazolyl, isothiazolyl, pyrazoly
, Imidazolyl, 1,3,4-oxadiazolyl,
1,2,4-oxadiazolyl, 1,3,4-thiadia
Zolyl, 1,2,4-thiadiazolyl, 1,2,4-to
Liazolyl, 1,2,3-thiadiazolyl, 1,2,3
-Triazolyl, 1,2,3,4-tetrazolyl, pyri
Jill, pyrimidinyl, pyrazinyl, pyridazinyl, 1,
Of 3,5-triazinyl and 1,2,4-triazinyl
Selected from inside. ) And T^TwoAnd T^ThreeAre independent
OH, phenyl, C₁~ C₆Alkyl, C₁~ C₆Al
Coxy or C₁~ C_FourAlkylsulfenyl, 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_FourAlkyl, C₁~ C_FourHaloalkyl,
C₁~ C_FourAlkoxy, C₁~ C_FourHaloalkoxy, C₁~
C_FourAlkylsulfenyl, C₁~ C_FourAlkylsulfi
Nil, C₁~ C_FourAlkylsulfonyl, C_Two~ C_FiveAlkene
Rusulfenyl, C_Two~ C_FiveAlkenylsulfinyl, C
_Two~ C_FiveAlkenylsulfonyl, C₁~ C_FourHaloalkyls
Luphenyl, C₁~ C_FourHaloalkylsulfinyl, C₁
~ C_FourHaloalkylsulfonyl, NO_Two, CN, CHO,
OH, -NU¹U^Two, Phenyl, phenoxy and C_Two~
C_FiveOne which is arbitrarily selected from alkoxycarbonyl
5 substituents, T⁷And T⁸Are each independently
H, phenyl, benzyl or C₁~ C₆Is alkyl
Or T⁷And T⁸Together with the carbon atom to which
May form a 5- to 8-membered ring,¹And U^TwoAre each
Independently, H, C₁~ C₆Alkyl, C_Two~ C_FiveAlkyl cal
Bonil, C_Two~ C_FiveAlkoxycarbonyl, phenyl or
Is benzyl or U¹And U^TwoTo which the carbon source is bound
And may form a 5- to 8-membered ring with the^aIs
Logen and C₁~ C_FourAt least one selected from alkyl
An optionally substituted phenyl,^bThe haloge
And C₁~ C_FourSubstituted with one or more selected from alkyl
Benzoyl which may be^cIs the halogen
And C₁~ C_FourSubstituted with at least one selected from alkoxy
An optionally substituted phenyl, R^dIs replaced by halogen
C which may be replaced_Two~ C_FourAlkenyl. ]
Isoxazole derivative.

[2] The isoxazole derivative according to [1], wherein Q is thiazolyl substituted with R.

[3] The isoxazole derivative according to [1], wherein Q is pyrazolyl substituted with R.

[4] An agricultural chemical comprising at least one of the isoxazole derivatives according to [1] to [3] as an active ingredient.

[0013]

BEST MODE FOR CARRYING OUT THE INVENTION In the compound (1) of the present invention, R is C = N
When containing -OR ² parts, although two isomers of E-form and Z-form are present, it is included in both cases the present invention.

Next, Q, A, G, R, R ¹ , R ² , R ³ ,
Y, W, X, Z, T 1, T 2, T 3, T 4, T 5, T 6,
Preferred ranges of T ⁷ , T ⁸ , U 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 or pyro
And oxazolyl is oxazole-2.
-Yl, oxazol-4-yl or oxazole-
5-yl, and thiazolyl is thiazol-2-yl,
Thiazol-4-yl or thiazol-5-yl, and imidazolyl is imidazol-1-yl, imidazol-2-yl or imidazol-4-yl;
Isoxazolyl is isoxazol-3-yl, isoxazol-4-yl or isoxazol-5-yl, isothiazolyl is isothiazol-3-yl, isothiazol-4-yl or isothiazol-5-yl, pyrazolyl is pyrazole -1-yl, pyrazo-
L-3-yl, pyrazol-4-yl or pyrazol-5-yl; 1,3,4-oxadiazolyl is 1,3,4-oxadiazol-2-yl;
3,4-thiadiazolyl is 1,3,4-thiadiazol-2-yl and 1,2,4-oxadiazolyl is 1,2,4-oxadiazol-3-yl or 1,
2,4-oxadiazol-5-yl;
4-thiadiazolyl is 1,2,4-thiadiazole-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;
1,2,3-thiadiazolyl is 1,2,3-thiadiazol-4-yl or 1,2,3-thiadiazole-5
-Yl and 1,2,3-triazolyl is 1,2,3
-Triazol-1-yl, 1,2,3-triazol-2-yl or 1,2,3-triazol-4-yl, wherein 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-tetrazol-5-yl, pyridyl being pyridin-2-yl, pyridin-3-yl Yl or pyridin-4-yl, and pyrimidinyl is pyrimidin-2-yl, pyrimidin-4-yl
Yl or pyrimidin-5-yl, pyrazinyl is pyrazin-2-yl and pyridazinyl is pyridazin-3-yl or pyridazin-4-yl;
3,5-triazinyl is 1,3,5-triazine-2-
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 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.

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, quinazolinyl and

[0027]

Embedded image

[0028]

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 and

[0030]

Embedded image

[0031]

RIII: thiazolyl, pyrimidinyl, pyrazinyl and

[0033]

Embedded image

[0034]

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.

Preferred ranges of R ² are the following groups.

That is, R ² I: H, C ₁ -C ₁₀ alkyl, C ₂
-C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkynyl, C ₁ -C ₃ optionally C ₃ optionally substituted with alkyl
-C ₆ cycloalkyl, C ₂ -C ₄ alkoxyalkyl,
_{CH 3 OC 2 H 4 OCH 2} , C substituted with R ^a ₁ -C ₄ alkyl, C ₁ -C ₄ alkyl substituted with R ^b, C ₂ ~C ₄ alkenyl substituted with R ^a, tetrahydropyranyl Le, C ₁
-C ₄ alkylsulfonyl, halogen or C ₁ -C ₄
Phenylsulfonyl optionally substituted with alkyl,
—SO ₂ CF ₃ , C ₁ -C ₄ monoalkylaminosulfonyl, C ₂ -C ₈ dialkylaminosulfonyl, phenylaminosulfonyl, phenyl optionally substituted with Z,
Pyridyl which may be substituted with Z, pyrimidinyl which may be substituted with Z, pyrazinyl optionally substituted by Z, C ₂ -C ₅ cyanoalkyl, -C (= O) T ¹ and -C ( = S) T ¹ .

R ² II: C ₁ -C ₁₀ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ haloalkyl,
C ₂ ~C ₆ haloalkenyl, C ₂ ~C ₆ haloalkynyl, C
₁ -C ₃ may be alkyl substituted C ₃ -C ₆ cycloalkyl, C ₂ -C ₄ alkoxyalkyl, CH ₃ OC ₂ H
₄ OCH ₂ , C ₁ -C ₄ alkyl substituted with ^Ra , tetrahydropyranyl, phenylsulfonyl optionally substituted with halogen or C ₁ -C ₄ alkyl, phenylaminosulfonyl, even substituted with Z Good phenyl,
Pyridyl which may be substituted with Z, pyrimidinyl which may be substituted with Z, pyrazinyl optionally substituted by Z, C ₂ -C ₅ cyanoalkyl, -C (= O) T ¹ and -C ( = S) T ¹ .

R ² III: C ₁ -C ₁₀ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkynyl , C ₃ -C ₆ optionally substituted with C ₁ -C ₃ alkyl
Cycloalkyl, C ₁ -C ₄ alkyl substituted with R ^a ,
Tetrahydropyranyl, phenyl optionally substituted by Z, pyridyl optionally substituted by Z, which may be pyrimidinyl and -C substituted by Z (= O) T ^1.

Preferred ranges of R ³ are the following groups.

That is, R ³ I: H, halogen, C ₁ -C ₁₀ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl,
_{1 ~C 6} haloalkyl, C ₂ ~C ₆ haloalkenyl, C ₂ ~
C ₆ haloalkynyl, C ₃ -C ₆ halocycloalkyl, C ₁
-C may be substituted with ₃ alkyl C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₄ alkyl substituted with R ^a, with R ^a substituted C ₂ -C ₄ alkenyl, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, optionally substituted by halogen or C ₁ -C ₄ alkyl Phenylsulfonyl, CN, -NU ¹
U ² , phenoxy, phenylamino, —C (＝ O) T ¹ ,
—C (＝ S) T ¹ , morpholinyl, piperidyl, pyrazolyl optionally substituted with Z, imidazolyl optionally substituted with Z, thiazolyl optionally substituted with Z, even substituted with Z Good phenyl, pyridyl optionally substituted with Z, pyrimidinyl optionally substituted with Z, and pyrazinyl optionally substituted with Z.

R ³ II: H, halogen, C ₁ -C ₁₀ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆
C ₆ haloalkyl, C ₂ ~C ₆ haloalkenyl, C ₂ ~C ₆
Haloalkynyl, C ₁ -C ₃ optionally substituted by alkyl C ₃ -C ₆ cycloalkyl, optionally substituted by CN and Z phenyl.

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
_A substituent arbitrarily selected from _{2 to} C ₄ haloalkylcarbonyloxy or phenyl optionally substituted by X (however, when two or more substituents are present, they may be the same or different). The number of the substituents is 1, 2 or 3.

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 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 heterocycle 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 with phenyl_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 preferable 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 preferable 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 of 0 to 3, preferably 0 or 1.

Preferred ranges of Z are the following groups.

That is, ZI: halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁
-C ₄ haloalkoxy, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₃ -C ₅ alkenyl Le phenyl, C ₃ ~
C ₅ alkenylsulfinyl, C ₃ -C ₅ alkenylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄
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 the ring substituted by Z. When the ring substituted by Z is phenyl, the number of Z is 0.
And is preferably an integer of 0 to 4, 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, 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 a number of Z is an integer from 0 to 2,
Preferably it is 1 or 2. The heterocycle is thienyl,
In the case of furyl, pyrazolyl, imidazolyl, pyrimidinyl, pyrazinyl or pyridazinyl, the number of Z is an integer from 0 to 3, preferably an integer from 0 to 2, and more preferably 1 or 2. When the heterocyclic ring is pyrrolyl or 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 the carbon atom to which U ¹ and U ² are bonded. , May form 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. , May form 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, GI,
RI, R ¹ I, R ² I, R ³ I, nI, YI, WI, T ¹ I, T
² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XI, ZI, T ⁷ I, T ⁸ I,
The compound of the present invention, which is U ¹ I or U ² I.

The preferred substituent ranges are AII, GII, R
I, R ¹ II, R ² I, R ³ I, nI, YI, WI, T ¹ I, T
² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XI, ZI, T ⁷ I, T ⁸ I,
The compound of the present invention, which is U ¹ I or U ² I.

The preferred substituent ranges are AII, GIII, R
I, R ² I, R ³ I, nII, 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.

The preferred substituent ranges are AIII, GIII, R
I, R ² I, R ³ I, nII, YI, T ¹ I, T ² I, T ³ I, T
^{4 I, T 5 I, T} 6 I, XI, ZI, T 7 I, T 8 I, a compound of the invention which is U ¹ I and U ² I.

The preferred ranges of the substituents are AIII, GII and RI.
I, R¹II, R^TwoI, R^ThreeI, nI, YII, T¹II, T^TwoI, T
^ThreeI, T^FourI, T^FiveI, T⁶I, XII, ZII, T⁷I, T⁸I, U¹I
And U ^TwoA compound of the present invention which is I.

The preferred range of the substituent is AIII, GIII, R
III, R ¹ II, R ² II, R ³ II, nI, YII, T ¹ III, T
² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XIII, ZII, T ⁷ I, T ⁸
The compounds of the present invention which are I, U ¹ I and U ² I.

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

Preferred ranges of the substituents are AIV, GIII and RI.
II, R^TwoII, R^ThreeII, nII, 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 AIV, GIII and RI.
II, R ² III, R ³ II, nII, YII, T ¹ III, T ² I, T
³ I, T ⁴ I, T ⁵ I, T ⁶ I, XIII, ZII, T ⁷ I, T ⁸ I, U ¹
The compound of the present invention, which is I and U ² I.

The preferred substituent ranges are AV, GIII and RII.
I, R ² II, R ³ II, n II, Y II, 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.

The preferred range of the substituent is AV, GIII, RII
I, R^TwoIII, R^ThreeII, nII, 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 AVI, GIII and RI.
II, R^TwoII, R^ThreeII, nII, 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 AVI, GIII and RI.
II, R ² III, R ³ II, nII, YII, T ¹ III, T ² I, T
³ I, T ⁴ I, T ⁵ I, T ⁶ I, XIII, ZII, T ⁷ I, T ⁸ I, U ¹
The compound of the present invention, which is I and U ² I.

Next, Q, A, G, R, R ¹ , R ² , R ³ ,
Y, W, X, Z, T 1, T 2, T 3, T 4, T 5, T 6,
Examples of each atom and group in the definition of T ⁷ , T ⁸ , U ¹ or U ² are shown.

The halogen atom in the definition of G, R ¹ , R ³ , 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. Atoms.

R ¹ , R ² , R ³ , G, T ¹ , T ² , T ³ ,
As the alkyl in the definition of T ⁴ , T ⁵ , T ⁶ , T ⁷ , T ⁸ , U ¹ , U ² , W, X, Y or Z, methyl, ethyl, n-propyl as a linear or branched alkyl , Isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, pentyl-1, pentyl-2, pentyl-3, 2-methylbutyl-1, 2-methylbutyl-2, 2-methylbutyl-3, 3-methylbutyl -1,
2,2-dimethylpropyl-1, hexyl-1, hexyl-2, hexyl-3, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1, 2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-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, etc. It is selected in the range of carbon number.

The alkenyl in the definition of G, R ² , R ³ , T ¹ , T ⁴ , T ⁵ , T ⁶ or W is ethenyl, 1-propenyl, 2-alkenyl as a linear or branched alkenyl.
Propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl- 2-butenyl,
2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-
2-propenyl, 1,2-dimethyl-2-propenyl,
1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2
-Pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2
-Methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-
4-pentenyl, 4-methyl-4-pentenyl, 1,1
-Dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-2-butenyl, 1,3 -Dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl,
3,3-dimethyl-2-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-
Butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-
2-propenyl and the like, and each is selected from the designated carbon number range.

The alkynyl in the definition of G, R ² , R ³ or W includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl and ethynyl as linear or branched alkynyl. -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, and each is selected from the designated carbon number range.

G, R ² , R ³ , T ¹ , W, X, Y or Z
As the haloalkyl in the definition of, as a straight-chain 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, fluorobutyl, chloro-n-pentyl, fluoro-n-pentyl, chloro-n
-Hexyl, fluoro-n-hexyl and the like,
Each of the specified carbon number ranges is selected.

In the definition of R ² , R ³ , W, T ¹ , T ⁴ , T ⁵ or T ⁶ , C ₃ -C ₆ cycloalkyl which may be substituted by C ₁ -C ₃ alkyl includes cycloalkyl Propyl,
1-methylcyclopropyl, 2,2,3,3-tetramethylcyclopropyl, cyclobutyl, 1-ethylcyclobutyl, 1-n-butylcyclobutyl, cyclopentyl, 1-methylcyclopentyl, cyclohexyl, 1-
Methylcyclohexyl, 4-methylcyclohexyl and the like can be mentioned.

In the definition of R ² , R ³ , W or T ¹ ,
Examples of the C ₁ -C ₄ alkyl substituted with ^Ra include benzyl, 2-chlorobenzyl, 3-bromobenzyl, 4-chlorobenzyl, 4-methylbenzyl, 4-tert-butylbenzyl, 1-phenylethyl, -(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 by 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 by 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 which may be substituted by C ₁ -C ₃ alkyl in the definition of T ¹ includes:
Cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexyloxy, 1-methylcyclopropoxy and the like.

In the definition of R ² , R ³ or T ¹ , the C ₂ -C ₄ alkenyl substituted by ^Ra is 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.

The alkoxy in the definition of G, R ³ , T ¹ , T ² , T ³ , W, X, Y or Z is methoxy, ethoxy, n-propoxy, isopropoxy as straight-chain or branched-chain alkoxy. , N-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 1,1-dimethylpropoxy, 1,2-dimethyl Propoxy, 2,2-dimethylpropoxy, 1-ethylpropyloxy, n-hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutyl Oxy,
1,2-dimethylbutyloxy, 1,3-dimethylbutyloxy, 2,2-dimethylbutyloxy, 2,3-dimethylbutyloxy, 3,3-dimethylbutyloxy,
1-ethylbutyloxy, 2-ethylbutyloxy,
1,1,2-trimethylpropyloxy, 1,2,2-
Trimethylpropyloxy, 1-ethyl-1-methylpropyloxy, 1-ethyl-2-methylpropyloxy, n-heptyloxy, n-octyloxy, n-nonyloxy, n-decyloxy and the like. It is selected from a range of carbon numbers.

C ₃ in the definition of R ² , R ³ , W or T ¹
Examples of the halocycloalkyl of -C ₆ include fluorocyclopropyl, difluorocyclopropyl, chlorocyclopropyl, dichlorocyclopropyl, 1-methyl-2,2
-Dichlorocyclopropyl, chlorocyclobutyl, dichlorocyclobutyl, chlorocyclopentyl, dichlorocyclopentyl, chlorocyclohexyl, dichlorocyclohexyl, tetrafluorocyclobutyl and the like.

G, R ¹ , R ³ , T ¹ , W, X, Y or Z
In the definition of -NU ¹ U ² , methylamino, ethylamino, n-propylamino, isopropylamino,
n-butylamino, isobutylamino, sec-butylamino, tert-butylamino, n-pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 1,1-dimethylpropylamino, , 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
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-tert-butylamino, methylpentylamino,
Methylhexylamino, ethylpropylamino, ethylisopropylamino, ethylbutylamino, ethyl-s
ec-butylamino, ethylisobutylamino, ethylpentylamino, ethylhexylamino, phenylamino, benzylamino, N-methylacetamide, N-ethylacetamide, N-phenylacetamide, N-acetylacetamide and the like. It is selected in the range of carbon number.

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

[0115] ^{G, R 3, T 1,} W, X, as C ₁ -C ₄ haloalkoxy in the definition of Y and Z are each C ₁ -C ₄
Straight-chain or branched-chain haloalkoxy,
Fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, dichlorofluoromethoxy, chloromethoxy, dichloromethoxy, trichloromethoxy, bromomethoxy, fluoroethoxy, chloroethoxy, bromoethoxy, difluoroethoxy, trifluoroethoxy,
Tetrafluoroethoxy, pentafluoroethoxy, trichloroethoxy, trifluorochloroethoxy, fluoropropoxy, chloropropoxy, bromopropoxy, fluorobutoxy, chlorobutoxy, fluoro-i
and so-propoxy and chloro-iso-propoxy.

The C ₁ -C ₄ alkylsulfenyl in the definition of G, R ³ , 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 definitions of G, R ³ , X, W, Y and Z, C ₁ -C ₄ alkylsulfinyl includes methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, iso-propylsulfinyl, n-butylsulfinyl, iso-butylsulfinyl, sec-butylsulfinyl, and tert-butylsulfinyl.

The C ₁ -C ₄ alkylsulfonyl in the definition of G, R ² , R ³ , W, X, Y and Z includes methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, iso-propylsulfonyl, n-butyl Sulfonyl, iso-butylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl.

C ₂ -C ₄ alkoxyalkyl in the definition of R ² , R ³ , W, T ¹ or Y includes C ₁ -C ₃ alkoxy-methyl, C ₁ -C ₂ alkoxy-ethyl,
Methoxyethoxymethyl and methoxypropyl and the like.

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.

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

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

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

The pyridyl optionally substituted with X in the definition of W includes 2-pyridyl optionally substituted with X, 3-pyridyl optionally substituted with X or 3-pyridyl optionally substituted with 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 represents alkylideneamino, benzylideneamino, arylideneamino or cycloalkylideneamino, methylideneamino, ethylideneamino, propylideneamino, isopropylideneamino, 4-methyl-2-pentylideneamino, cyclopentylideneamino, cyclohexylidene And denamino.

Examples of the C ₁ -C ₄ monoalkylaminosulfonyl in the definition of R ² include methylaminosulfonyl, ethylaminosulfonyl, n-propylaminosulfonyl, isopropylaminosulfonyl, n-butylaminosulfonyl and the like.

As the C ₂ -C ₈ dialkylaminosulfonyl in the definition of R ² , dimethylaminosulfonyl,
Diethylaminosulfonyl, di-n-propylaminosulfonyl, diisopropylaminosulfonyl and di-n
-Butylaminosulfonyl and the like.

In the definition of R ² or R ³ , C ₁ -C ₄ alkyl substituted by R ^b includes phenacyl, 2-fluorophenacyl, 3-chlorophenacyl, 4-bromophenacyl, 2-methylphenacyl , 3-ethylphenacyl, 4-i-propylphenacyl, 4-t-butylphenacyl and the like.

In the definition of R ² or R ³ , phenylsulfonyl optionally substituted by one or more selected from a halogen atom and C ₁ -C ₄ alkyl includes 2-fluorophenylsulfonyl, 4-fluorophenylsulfonyl 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 R ² or R ³ includes cyanomethyl, 2-cyanoethyl, 3-cyanopropyl, 1-cyano-1-methylethyl and the like.

C ₃ -C ₉ alkoxycarbonylalkyl in the definition of R ² or R ³ includes methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propoxycarbonylmethyl, i-propoxycarbonyl as linear or branched alkoxycarbonylalkyl. Methyl, n-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- And propoxycarbonyl-1-methylethyl, 1-ethoxycarbonyl-2-methylpropyl and the like.

The alkali metal in the definition of R ² includes lithium, sodium and potassium.

As the alkaline earth metal in the definition of R ² , magnesium, calcium, strontium or barium can be mentioned, and preferably, magnesium, calcium or barium can be mentioned.

R^TwoIn the definition of^FourT^FiveT⁶Indicated by
Ammonium Nium, monomethyla
Ammonium, dimethylammonium, trimethylammonium
, Diethylammonium, triethylammonium
System, diisopropylammonium, diisopropylethyl
Ruammonium, hexylmethylammonium, cyclo
Propylmethylammonium, cyclohexylmethyla
Ammonium, allylmethylammonium, benzylmethy
Ammonium or 4-methylcyclohexylethyl
Ammonium or T^Four, T^FiveAnd T⁶Horse
The other two together with the nitrogen atom to which each is attached
Complexes which may contain elemental, nitrogen or sulfur atoms
Cyclic 5-, 6-, 7- or 8-membered ammonium
And the like.

T ⁴ , T ^{5 in} the definition of T ⁴ , T ⁵ or T ⁶
Heterocyclic 5-, 6-, 7- or 8-membered heterocyclic ring which may contain an oxygen atom, a nitrogen atom or a sulfur atom together with the nitrogen atom to which two of ⁵ and T ⁶ are bonded respectively. 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 R ² , R ³ , G or W includes C ₂ -C ₄ straight-chain or branched haloalkenyl such as 2-chloroethenyl, 2-bromoethenyl, 2,2-dichloroethenyl and the like. Is raised.

Alkenyloxy in the definition of R ³ , G, T ¹ , W or Y includes allyloxy, 2-propenyloxy, 2-butenyloxy and 2-methyl-2-propenyloxy as linear or branched alkenyloxy. And the like.

As the haloalkenyloxy in the definition of R ³ , G, W or Y, 3-chloro-2-propenyloxy, 3,3-dichloro-2-propenyloxy, as a linear or branched haloalkenyloxy, 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.

Alkenylsulfinyl in the definition of G, W, X, Y or Z includes allylsulfinyl and 2-alkenylsulfinyl as linear or branched alkenylsulfinyl.
Propenylsulfinyl, 2-butenylsulfinyl, 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 straight-chain or branched haloalkenylsulfenyl, 3,3-dichloro-2-propenylsulfenyl,
4,4-dichloro-3-butenylsulfenyl, 4,4
-Difluoro-3-butenylsulfenyl and the like.

As the haloalkenylsulfinyl in the definition of G, W or Y, 3-chloro-2-propenylsulfinyl, 3,3-dichloro-2-propenylsulfinyl, 4-chloro -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.

Haloalkynyl in the definition of R ² , R ³ , G or W includes chloroethynyl, bromoethynyl, iodoethynyl, 3-chloro-1-propynyl, 3
-Bromo-1-butynyl and the like.

The alkynyloxy in the definition of R ³ , G, W or Y includes 2-propynyloxy, 2-butynyloxy, 1-methyl-2-propynyloxy and the like.

Examples of haloalkynyloxy in the definition of R ³ , G, W or Y include 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-alkynylsulfonyl,
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.

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 optionally 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 damage agricultural and horticultural crops and trees, so-called livestock pests that infest livestock and poultry, so-called sanitary pests that have various adverse effects on human living environments such as houses, and warehouses. So-called stored pests that injure stored grains and the like, and any pests such as mites, nematodes, 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. japonica, P. serrata, P. serrata, S. serrata, S. aureus s.
Lepidopteran pests such as tobacco bud worm, European corn borer, fall army worm, codling moth and American white starling, black leafhopper, brown leafhopper, peach peach aphid, cotton aphid, onyx whitefly, silver leaf whitefly, pear whitefly, tsutsugunebayashiya Hemiptera pests such as scale insects, ruby beetles, giant brassies, giant clam bugs, locusts and bedbugs, bedbugs, scorpions, scorpions, beetles, rice weevil, weevil sword beetle, beetle beetle Arigata kanekushi, Matsunodara beaked beetle, Kansame bezel, Himehiratakeshikisui Coleopteran pests such as corn rootworm, coco elephant, granary weevil, and foxglove Drosophila, Tokunagakuronukaka,
Diptera pests such as Culex pipiens, Aedes aegypti, Aedes albopictus and Anopheles chinensis, abra wasps, pine saw wasps, kurihabees, guntai ants, black ants, giant hornets, bulldog ant, fire ant and pharaoh ant, etc. Thrips, Thrips thrips and Thrips palmi such as Thysanoptera, pests such as black cockroaches, Yamato cockroaches and German cockroaches, Kera, Emma cricket,
Orthopterous pests such as Tonosama grasshopper, Kobanineago and Saba-kuttari grasshopper, termite pests such as house termites, Yamato termites and Thai termites, isoptera pests such as cat flea, human flea and cheops muskleaf, and chick lice and lice Eye pests, lice such as bovine lice, porcine lice, bullfinch lice and porphyrus lice; total tail pests such as yamatoshimi; Spider mites such as Spider mite, Red rust mite, Red rust mite, Tulip rust mite and Dermatophagoides farinae; Lips such as acarid mites such as Acarina mites and Robin mite, house mites such as honey beetle mites, ticks such as ox tick and Haemaphysalis longicornis, narcissus mites such as sheep ticks, narcissus mites such as narcissus, lipsticks such as tobism mosquitoes, akasumkade, and swordfish Nematodes such as diplopods such as, scabies, fusidae, sweet potato nematodes, red rooted nematodes, northern nematodes, walnut nematodes, potato cyst nematodes and pine wood nematodes;
Examples include mollusks such as slugs, African snails, Usukawa maimai, and Miss snails, and crustaceans such as okadan bugs.

The plant disease to be controlled by the compound of the present invention includes rice blast (Pyriculari).
a oryzae), Sesame leaf blight (Cochliobo)
rus miyabeanus, Sheath blight (Rhizo)
ctonia solani), powdery mildew of wheat (Erysiphe graminis f. sp.h)
ordei, f. sp. tritici), leaf spot disease (P
erynophoragraminea, reticulum disease (P
yrenophora teres, Fusarium head blight (Gi
berella zeae), rust (Puccin)
ia striiformis, p. gramini
s, P. recondita, P .; hordei), snow rot (Typhula sp., Micronectr)
iellaniivais, naked smut (Ustilag)
o tritici, U.S.A. nuda), eye spot (Pseudocercosporella herp)
otrichoides, Rhynchos
porium secalis, Leaf blight (Septo)
ria tritici), Leaf blight (Leptosph)
aeria nodorum, citrus black spot (D
iaporthe citri), scab (Elsi)
noe faucetti), fruit rot (Penic)
illium digitatum, P .; italic
um), Monilia disease of apples (Sclerotinia)
mali), rot (Valsamali), powdery mildew (Podosphaera leucotric)
ha), spot leaf rot (Alternaria mal)
i), scab (Venturianaequali)
s), Pear scab (Venturia nasic)
ola), black spot (Alternaria Kikuc)
hiana), scab (Gymnosporangiu)
m haraeanum, peach scab (Schler)
otinia cinerea, scab (Clado)
sporium carpophilum, Phomopsis sp., downy mildew of grape (Plasmopara viticola),
Black rot (Elsinoe ampelina), late rot (Glomerella singulata), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidi)
s), oyster anthracnose (Gloeosporium ka)
ki), deciduous disease (Cercospora kaki, M)
ycosphaerella nawae), downy mildew of cucumber (Pseudoperenospora cub)
ensis), Anthracnose (Colletotrichum)
lagenarium), powdery mildew (Sphaer)
otheca fuliginea, vine blight (My
cosphaerella melonis, tomato blight (Phytophthora infestan)
s), ring spot disease (Alternaria solan)
i), leaf mold disease (Cladosporium fulva)
m), eggplant brown spot (Phomopsis vexan)
s), powdery mildew (Erysiphe cichola)
coarum), black spot of cruciferous vegetables (Alter)
naria japonica, vitiligo disease (Ceroc)
osporella brassicae, green onion rust (Puccinia allii), soybean purpura (Cercospora kikuchii), black rot (Elsinoe glycines), black spot (Diaporthephaelolumen colodium ulcer disease)
emutianum), Peanut black spot (Myc)
osphaerella personatum, brown spot (Cercospora arachidicol)
a), Pea powdery mildew (Erysiphe pi)
si), potato summer blight (Alternaria)
solani), strawberry powdery mildew (Sphaero)
theca humuli), tea net blast (Exo)
basidium reticulatum), scab (Elsinoe leucospila), tobacco scab (Alternaria longipes),
Powdery mildew (Erysiphe cichoracea)
rum), anthracnose (Colletotrichum t)
abacum), brown spot of sugar beet (Cercospo)
ra beticola, rose scab (Diplo)
carpon rosea, powdery mildew (Sphae)
rotheca pannosa), brown spot of chrysanthemum (S
eptoria chrysanthemiindic
i), white rust (Puccinia horian)
a), Botrytis c of various crops
innerea), sclerotium disease of various crops (Sclerot)
inia sclerotiorum) and the like.

That is, the compounds of the present invention 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

[0167]

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[Q and A in (Scheme 1) are as defined above.
Meaning R^FourIs a hydrogen atom or C₁~ C₆Archi
R^FiveIs C₁~ C₆Represents an alkyl. Also, R^Four
And R ^FiveTogether form a ring having 3 to 8 carbon atoms
Is also good. That is, the compound represented by the formula (2)
By reacting droxylamine or its salt
Thus, a compound represented by the formula (1) can be obtained.

Examples of the salt of hydroxylamine used in the reaction include hydrochloride, sulfate, oxalate and the like. If desired, a catalyst such as p-toluenesulfonic acid, sulfuric acid or Lewis acid may be added.

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, and 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. The reaction temperature can be set at any temperature from -30 ° C to 200 ° C, and preferably from 0 ° C to 150 ° C or from 0 ° C to the boiling point of the solvent when a solvent is used.

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, column chromatography and the like. Can be.

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

Compound (2) in (Scheme 1) can be synthesized according to the method described in International Patent Application Publication (WO 99/02507).

Examples of the compounds included in the present invention are shown in Tables 1 and 2. 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,

[0176]

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[0177]

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[0178]

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[0179]

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[Table 1]

[0181]

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[0182]

[Table 1] ――――――――――――――――――――――――――――――――― RR ¹ G A ――――――― R1 HH A1 R1 HH A2 R1 HH A3 R1 HH A4 R1 HH A10 R1 H 3-Me A10 R1 HH A11 R1 HH A12 R1 HH A24 R1 HH A25 R1 HH A31 R1 HH A32 R1 HH A45 R1 HH A48 R2 HH A1 R2 HH A2 R2 HH A3 R2 HH A4 R2 HH A10 R2 HH A11 R2 HH A12 R2 HH A24 R2 HH A24 H R2 HH A31 R2 HH A32 R2 HH A45 R2 HH A48 R3 H 1-Me A1 R3 H 1-Me A2 R3 H 1-Me A3 R3 H 1-Me A4 R3 H 1-Me A10 R3 H 1-Me A11 R3 H 1-Me A12 R3 H 1-Me A24 R3 H 1-Me A25 R3 H 1-Me A31 R3 H 1-Me A32 R3 H 1-Me A45 R3 H 1-Me A48 R4 HH A1 R4 HH A2 R4 HH A10 R4 HH A25 R4 HH A31 R4 HH A32 R4 HH A45 R4 HH A48 R5 HH A1 R5 H 5-Me A1 R5 HH A2 R5 HH A10 R5 HH A25 R5 HH A31 R5 HH A32 R5 HH A45 R5 HH A48 R6 HH A1 R6 HH A2 R6 HH A3 R6 HH A4 R6 HH A10 R6 HH A11 R6 HH A12 R6 HH A24 R6 HH A25 R6 HH A31 R6 HH A32 R6 HH A45 R6 HH A48 R7 HH A1 R7 HH A2 R7 HH A 10 R7 HH A25 R7 HH A31 R7 HH A32 R7 HH A45 R7 HH A48 R8 HH A1 R8 HH A2 R8 HH A10 R8 HH A25 R8 HH A31 R8 HH A32 R8 HH A45 R8 HH A48 R9 HH A1 R9 HH A2 R9 HH R10 HH A25 R9 HH A31 R9 HH A32 R9 HH A45 R9 HH A48 R10 HH A1 R10 HH A2 R10 HH A10 R10 HH A25 R10 HH A31 R10 HH A32 R10 HH A45 R10 HH A48 R11 HH A1 R11 HH A2 R11 HH A10 H11 AH R11 HH A31 R11 HH A32 R11 HH A45 R11 HH A48 R12 HH A1 R12 Me H A1 R12 HH A2 R12 Cl H A2 R12 HH A3 R12 HH A4 R12 HH A5 R12 HH A6 R12 HH A7 R12 HH A8 R12 HH A9 R12 HH10 R12 Me H A10 R12 Cl H A10 R12 CO ₂ Me H A10 R12 NO ₂ H A10 R12 CN H A10 R12 NMe ₂ H A10 R12 HH A11 R12 HH A12 R12 HH A13 R12 HH A14 R12 HH A15 R12 HH A16 R12 HH A17 R12 HH A18 R12 HH A19 R12 HH A20 R12 HH A21 R12 HH A22 R12 HH A23 R12 HH A24 R12 HH A25 R12 HH A26 R12 HH A27 R12 HH A28 R12 HH A29 R12 HH A30 R12 HH A31 R12 HH A32 R12 HH A33 R12 HH A33 H12 R12 HH A35 R12 HH A36 R12 HH A37 R12 HH A38 R12 HH A39 R12 HH A40 R12 HH A41 R12 HH A42 R12 HH A43 R12 HH A44 R12 HH A45 R12 HH A46 R12 HH A47 R12 HH A48 R12 HH A49 R12 HH A50 R12 HH A51 R12 HH A52 R12 HH A53 R12 HH A54 R12 HH A55 R12 HH A56 R12 HH A57 R12 HH A58 R12 HH A59 R12 HH A60 R12 HH A61 R13 HH A1 R13 HH A2 A10 R13 HH A25 R13 HH A31 R13 HH A32 R13 HH A45 R13 HH A48 R14 HH A1 R14 HH A2 R14 HH A10 R14 HH A25 R14 HH A31 R14 HH A32 R14 HH A45 R14 HH A48 R15 HH A1 R15 HH A2 R15 HA HH A25 R15 HH A31 R15 HH A32 R15 HH A45 R15 HH A48 R16 HH A1 R16 H 5-Cl A1 R16 HH A2 R16 H 3,5-Me ₂ A2 R16 HH A10 R16 H 3-CF ₃ A10 R16 H 4-NO ₂ A10 R16 H 4-CN A10 R16 H 4-CO ₂ Me A10 R16 H 3-COMe A10 R16 HH A25 R16 HH A31 R16 HH A32 R16 HH A45 R16 HH A48 R17 H 1-Me A1 R17 H 1-Me A2 R17 H 1-Me A10 R17 H 1-Me A25 R17 H 1-Me A31 R17 H 1-Me A32 R17 H 1-Me A45 R17 H 1-Me A48 R18 H 1-Me A1 R18 HH A2 R18 H 1-Me A2 R18 H 1-Me A10 R18 H 1-Me A25 R18 H 1-Me A31 R18 H 1-Me A32 R18 H 1-Me A45 R18 H 1-Me A48 R19 HH A1 R19 H 1-Me A1 R19 H 1-Me A2 R19 HH A10 R19 H 1-Me A10 R19 H 1-Et A10 R19 H 1-CH = CH ₂ A10 R19 H 1-CH ₂ CH = CH ₂ A10 R19 H 1-CH ₂ CH = CCl ₂ A10 R19 H 1-CH ₂ C≡CH A10 R19 HH A25 R19 HH A31 R19 HH A32 R19 HH A45 R19 HH A48 R20 H 1-Me A1 R20 H 1-Me A2 R20 H 1-Me A10 R20 H 1-Me A25 R20 H 1-Me A31 R20 H 1-Me A32 R20 H 1-Me A45 R20 H 1-Me A48 R21 H 1-Me A1 R21 H 1-Me A2 R21 H 1-Me A10 R21 H 1- Me A25 R21 H 1-Me A31 R21 H 1-Me A32 R21 H 1-Me A45 R21 H 1-Me A48 R22 HH A1 R22 H 2-Me A1 R22 HH A2 R22 HH A10 R22 H 2-Me A10 R22 H 2 -Me A25 R22 H 2-Me A31 R22 H 2-Me A32 R22 H 2-Me A45 R22 H 2-Me A48 R23 HH A1 R23 H 3-Me A1 R23 H 3-Me A2 R23 H 3-Me A10 R23 H 3-Me A25 R23 H 3-Me A31 R23 H 3-Me A32 R23 H 3-Me A45 R23 H 3-Me A48 R24 H 5-Me A1 R24 H 5-Me A2 R24 HH A10 R24 H 5-Me A10 R24 H 5-Me A25 R24 H 5-Me A31 R24 H 5-Me A32 R24 H 5-Me A45 R24 H 5-Me A48 R25 H 2-Me A1 R25 HH A2 R25 H 2-Me A2 R25 HH A10 R25 H 2 -Me A10 R25 H 2-Me A25 R25 H 2-Me A31 R25 H 2-Me A32 R25 H 2-Me A45 R25 H 2-Me A48 R26 H 3-Me A1 R26 H 3-Me A2 R26 HH A10 R26 H 3-Me A10 R26 H 3-Me A25 R26 H 3-Me A31 R26 H 3-Me A32 R26 H 3-Me A45 R26 H 3-Me A48 R27 H 5-Me A 1 R27 H 5-Me A2 R27 HH A10 R27 H 5-Me A10 R27 H 5-Me A25 R27 H 5-Me A31 R27 H 5-Me A32 R27 H 5-Me A45 R27 H 5-Me A48 R28 H 1- Me A1 R28 H 1-Me A2 R28 H 1-Me A10 R28 H 1-Me A25 R28 H 1-Me A31 R28 H 1-Me A32 R28 H 1-Me A45 R28 H 1-Me A48 R28 H 2-Me A1 R28 H 2-Me A2 R28 H 2-Me A10 R28 H 2-Me A25 R28 H 2-Me A31 R28 H 2-Me A32 R28 H 2-Me A45 R28 H 2-Me A48 R28 H 4-Me A1 R28 H 4-Me A2 R28 H 4-Me A10 R28 H 4-Me A25 R28 H 4-Me A31 R28 H 4-Me A32 R28 H 4-Me A45 R28 H 4-Me A48 R29 H 4-Me A1 R29 HH A2 R29 H 4-Me A2 R29 HH A10 R29 H 4-Me A10 R29 HH A25 R29 HH A31 R29 HH A32 R29 HH A45 R29 HH A48 R30 HH A1 R30 HH A2 R30 HH A10 R30 H 5-Me A10 R30 HH A25 R30 HH A31 R30 HH A32 R30 HH A45 R30 HH A48 R31 H 1-Me A1 R31 H 1-Me A2 R31 H 1-Me A10 R31 H 2-Me A10 R31 H 1-Me A25 R31 H 2-Me A25 R31 H 1-Me A31 R31 H 1-Me A32 R31 H 1-Me A45 R31 H 1-Me A48 R32 H 1-Me A1 R32 H 1-Me A2 R32 H 1-Me A10 R32 H 1-Me A25 R32 H 1-Me A31 R32 H 1-Me A32 R32 H 1-Me A45 R32 H 1-Me A48 R33 HH A1 R33 Cl H A1 R33 HH A2 R33 Cl H A2 R33 HH A3 R33 HH A4 R33 HH A5 R33 HH A6 R33 HH A7 R33 HH A8 R33 HH A9 R33 HH A10 R33 Me H A10 R33 Cl H A10 R33 HH A11 R33 HH A12 R33 HH A13 R33 HH A14 R33 HH A15 R33 HH A16 R33 HH A17 R33 HH A18 R33 HH A19 R33 HH A20 R33 HH A21 R33 HH A22 R33 HH A23 R33 HH A24 R33 HH A25 R33 HH A26 R33 HH A27 R33 HH A28 R33 HH A29 R33 HH A30 R33 HH A33 R33 HH A32 A33 R33 HH A34 R33 HH A35 R33 HH A36 R33 HH A37 R33 HH A38 R33 HH A39 R33 HH A40 R33 HH A41 R33 HH A42 R33 HH A43 R33 HH A44 R33 HH A45 R33 Cl H A45 R33 HH A46 R33 HH A47 R33 HH A48 R33 Cl H A48 R33 HH A49 R33 HH A50 R33 HH A51 R33 HH A52 R33 HH A53 R33 HH A54 R33 HH A55 R33 HH A56 R33 HH A57 R33 HH A58 R33 HH A59 R33 HH A60 R33 HH A61 R34 HH A1 R34 HH R2 HH A10 R34 HH A25 R34 HH A31 R34 HH A32 R34 HH A45 R34 HH A48 R35 HH A1 R35 HH A2 R35 HH A10 R35 HH A25 R35 HH A31 R35 HH A32 R35 HH A45 R35 HH A48 R36 HH A1 R36 Cl H A1 R36 H 3-Me A1 R36 Cl 3-Me A1 R36 HH A2 R36 H 3-Me A2 R36 H 3-Et A2 R36 Me H A2 R36 Cl H A2 R36 HH A 3 R36 HH A4 R36 HH A5 R36 HH A6 R36 HH A7 R36 HH A8 R36 HH A9 R36 HH A10 R36 H 3-Me A10 R36 H 3-Et A10 R36 Me H A10 R36 Cl H A10 R36 CO ₂ Me H A10 R36 HH A11 R36 HH A12 R36 HH A13 R36 HH A14 R36 HH A15 R36 HH A16 R36 HH A17 R36 HH A18 R36 HH A19 R36 HH A20 R36 HH A21 R36 HH A22 R36 HH A23 R36 HH A24 R36 H 3-Me A24 R36 H 3- Et A24 R36 Cl H A24 R36 HH A25 R36 H 3-Me A25 R36 H 3-Et A25 R36 Cl H A25 R36 HH A26 R36 HH A27 R36 HH A28 R36 HH A29 R36 HH A30 R36 HH A31 R36 H 3-Me A32 R36 HH A32 R36 HH A33 R36 HH A34 R36 HH A35 R36 HH A36 R36 HH A37 R36 HH A38 R36 HH A39 R36 HH A40 R36 HH A41 R36 HH A42 R36 HH A43 R36 HH A44 R36 HH A45 R36 H3-Me A45 R36 Cl H A45 R36 HH A46 R36 HH A47 R36 HH A48 R36 H3-Me A48 R36 Cl H A48 R36 HH A49 R36 HH A50 R36 HH A51 R36 HH A52 R36 HH A53 R36 HH A54 R36 HH A55 R36 HH A56 R36 HH A57 R36 HH A58 R36 HH A59 R36 HH A60 R36 HH A61 R37 HH A1 R37 HH A2 R37 HH A10 R37 HH A25 R37 HH A31 R37 HH A32 R37 HH A45 R37 HH A48 R38 HH A1 R38 HH A2 R38 HH A10 R38 HH A25 R38 HH A31 R38 HH A32 R38 HH A45 R38 HH A48 R39 HH A1 R39 HH A2 R39 HH A10 R39 HH A25 R39 HH A31 R39 HH A32 R39 HH A45 R39 HH A48 R40 HH A1 R40 HH A2 R40 HH A10 R40 HH A25 R40 HA HH A32 R40 HH A45 R40 HH A48 R41 HH A1 R41 HH A2 R41 HH A10 R41 HH A25 R41 HH A31 R41 HH A32 R41 HH A45 R41 HH A48 R42 HH A1 R42 HH A2 R42 HH A10 R42 HH A25 R42 HH A31 R42 HH A31 H R42 HH A45 R42 HH A48 ――――――――――――――――――――――――――――――――――― [Table 2]

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[0184]

[Table 2] ――――――――――――――――――――――――――――――――――― RR ¹ R ² R ³ A ―――― ――――――――――――――――――――――――――――――― R43 HHH A1 R43 H Me H A1 R43 H Me Me A1 R43 Cl Me Me A1 R43 H Me Et A1 R43 H Me nPr A1 R43 H Me cPr A1 R43 H Me CF ₃ A1 R43 H Me Ph A1 R43 H Me CO ₂ Me A1 R43 H Et Me A1 R43 H CH ₂ CH = CH ₂ Me A1 R43 H CH ₂ C≡CH Me A1 R43 H CH ₂ CH ₂ CH ₂ F Me A1 R43 H CH ₂ CH = CCl ₂ Me A1 R43 H cPr Me A1 R43 H CH ₂ Ph Me A1 R43 H Ph Me A1 R43 H SO ₂ CF ₃ Me A1 R43 H COMe Me A1 R43 H COtBu Me A1 R43 HHH A2 R43 H Me H A2 R43 H Me Me A2 R43 Cl Me Me A2 R43 H Me Et A2 R43 H Me nPr A2 R43 H Me cPr A2 R43 H Me CF ₃ A2 R43 H Me Ph A2 R43 H Me CO ₂ Me A2 R43 H Et Me A2 R43 H CH ₂ CH = CH ₂ Me A2 R43 H CH ₂ C≡CH Me A2 R43 H CH ₂ CH ₂ CH ₂ F Me A2 R43 H CH ₂ CH = CCl ₂ Me A2 R43 H cPr Me A2 R43 H CH ₂ Ph Me A2 R43 H Ph Me A2 R43 H SO ₂ CF ₃ Me A2 R43 H COMe Me A2 R43 H COtBu Me A2 R43 H Me Me A3 R43 H Me Et A3 R43 H Me CO ₂ Me A3 R43 H Et Me A3 R43 H CH ₂ CH = CH ₂ Me A3 R43 H COMe Me A3 R43 H COtBu Me A3 R43 H Me Me A4 R43 H Me Et A4 R43 H Me CO ₂ Me A4 R43 H Et Me A4 R43 H CH ₂ CH = CH ₂ Me A4 R43 H COMe Me A4 R43 H COtBu Me A4 R43 H Me Me A5 R43 H Et Me A5 R43 H Me CO ₂ Me A5 R43 H CH ₂ CH = CH ₂ Me A5 R43 H Me Me A6 R43 H Et Me A6 R43 H Me CO ₂ Me A6 R43 H CH ₂ CH = CH ₂ Me A6 R43 H Me Me A7 R43 H Et Me A7 R43 H Me CO ₂ Me A7 R43 H CH ₂ CH = CH ₂ Me A7 R43 H Me Me A8 R43 H Et Me A8 R43 H Me CO ₂ Me A8 R43 H CH ₂ CH = CH ₂ Me A8 R43 H Me Me A9 R43 H Et Me A9 R43 H Me CO ₂ Me A9 R43 H CH ₂ CH = CH ₂ Me A9 R43 HHH A10 R43 H Me H A10 R43 H Me Me A10 R43 Me Me Me A10 R43 Cl Me Me A10 R43 CO ₂ Me Me Me A10 R43 NO ₂ Me Me A10 R43 CN Me Me A10 R43 NMe ₂ Me Me A10 R43 H Me Et A10 R43 H Me nPr A10 R43 H Me cPr A10 R43 H Me CF ₃ A10 R43 H Me Ph A10 R43 H Me CO ₂ Me A10 R43 H Et Me A10 R43 H CH ₂ CH = CH ₂ Me A10 R43 H CH ₂ C≡CH Me A10 R43 H CH ₂ CH ₂ CH ₂ F Me A10 R43 H CH ₂ C H = CCl ₂ Me A10 R43 H cPr Me A10 R43 H CH ₂ Ph Me A10 R43 H Ph Me A10 R43 H SO ₂ CF ₃ Me A10 R43 H COMe Me A10 R43 H COtBu Me A10 R43 H Me Me A11 R43 H Me Et A11 R43 H Me CO ₂ Me A11 R43 H Et Me A11 R43 H CH ₂ CH = CH ₂ Me A11 R43 H COMe Me A11 R43 H COtBu Me A11 R43 H Me Me A12 R43 H Me Et A12 R43 H Me CO ₂ Me A12 R43 H Et Me A12 R43 H CH ₂ CH = CH ₂ Me A12 R43 H COMe Me A12 R43 H COtBu Me A12 R43 H Me Me A13 R43 H Et Me A13 R43 H Me CO ₂ Me A13 R43 H CH ₂ CH = CH ₂ Me A13 R43 H Me Me A14 R43 H Et Me A14 R43 H Me CO ₂ Me A14 R43 H CH ₂ CH = CH ₂ Me A14 R43 H Me Me A15 R43 H Et Me A15 R43 H Me CO ₂ Me A15 R43 H CH ₂ CH = CH ₂ Me A15 R43 H Me Me A16 R43 H Et Me A16 R43 H Me CO ₂ Me A16 R43 H CH ₂ CH = CH ₂ Me A16 R43 H Me Me A17 R43 H Et Me A17 R43 H Me CO ₂ Me A17 R43 H CH ₂ CH = CH ₂ Me A17 R43 H Me Me A18 R43 H Et Me A18 R43 H Me CO ₂ Me A18 R43 H CH ₂ CH = CH ₂ Me A18 R43 H Me Me A19 R43 H Et Me A19 R43 H Me CO ₂ Me A19 R43 H CH ₂ CH = CH ₂ Me A19 R43 H Me Me A20 R43 H Et Me A20 R43 H Me CO ₂ Me A20 R 43 H CH ₂ CH = CH ₂ Me A20 R43 H Me Me A21 R43 H Et Me A21 R43 H Me CO ₂ Me A21 R43 H CH ₂ CH = CH ₂ Me A21 R43 H Me Me A22 R43 H Et Me A22 R43 H Me CO ₂ Me A22 R43 H CH ₂ CH = CH ₂ Me A22 R43 H Me Me A23 R43 H Et Me A23 R43 H Me CO ₂ Me A23 R43 H CH ₂ CH = CH ₂ Me A23 R43 H Me Me A24 R43 H Me Et A24 R43 H Me CO ₂ Me A24 R43 H Et Me A24 R43 H CH ₂ CH = CH ₂ Me A24 R43 H COMe Me A24 R43 H COtBu Me A24 R43 HHH A25 R43 H Me H A25 R43 H Me Me A25 R43 H Me Et A25 R43 H Me nPr A25 R43 H Me cPr A25 R43 H Me CF ₃ A25 R43 H Me Ph A25 R43 H Me CO ₂ Me A25 R43 H Et Me A25 R43 H CH ₂ CH = CH ₂ Me A25 R43 H CH ₂ C≡ CH Me A25 R43 H CH ₂ CH ₂ CH ₂ F Me A25 R43 H CH ₂ CH = CCl ₂ Me A25 R43 H cPr Me A25 R43 H CH ₂ Ph Me A25 R43 H Ph Me A25 R43 H SO ₂ CF ₃ Me A25 R43 H COMe Me A25 R43 H COtBu Me A25 R43 H Me Me A26 R43 H Et Me A26 R43 H Me CO ₂ Me A26 R43 H CH ₂ CH = CH ₂ Me A26 R43 H Me Me A27 R43 H Et Me A27 R43 H Me CO ₂ Me A27 R43 H CH ₂ CH = CH ₂ Me A27 R43 H Me Me A28 R43 H Et Me A28 R43 H Me CO ₂ Me A28 R43 H CH ₂ CH = CH ₂ Me A28 R43 H Me Me A29 R43 H Et Me A29 R43 H Me CO ₂ Me A29 R43 H CH ₂ CH = CH ₂ Me A29 R43 H Me Me A30 R43 H Et Me A30 R43 H Me CO ₂ Me A30 R43 H CH ₂ CH = CH ₂ Me A30 R43 HHH A31 R43 H Me H A31 R43 H Me Me A31 R43 H Me Et A31 R43 H Me nPr A31 R43 H Me cPr A31 R43 H Me CF ₃ A31 R43 H Me Ph A31 R43 H Me CO ₂ Me A31 R43 H Et Me A31 R43 H CH ₂ CH = CH ₂ Me A31 R43 H CH ₂ C≡CH Me A31 R43 H CH ₂ CH ₂ CH ₂ F Me A31 R43 H CH ₂ CH = CCl ₂ Me A31 R43 H cPr Me A31 R43 H CH ₂ Ph Me A31 R43 H Ph Me A31 R43 H SO ₂ CF ₃ Me A31 R43 H COMe Me A31 R43 H COtBu Me A31 R43 HHH A32 R43 H Me H A32 R43 H Me Me A32 R43 H Me Et A32 R43 H Me nPr A32 R43 H Me cPr A32 R43 H Me CF ₃ A32 R43 H Me Ph A32 R43 H Me CO ₂ Me A32 R43 H Et Me A32 R43 H CH ₂ CH = CH ₂ Me A32 R43 H CH ₂ C≡CH Me A32 R43 H CH ₂ CH ₂ CH ₂ F Me A32 R43 H CH ₂ CH = CCl ₂ Me A32 R43 H cPr Me A32 R43 H CH ₂ Ph Me A32 R43 H Ph Me A32 R43 H SO ₂ CF ₃ Me A32 R43 H COMe Me A32 R43 H COtBu Me A32 R43 H Me Me A33 R43 H Et Me A33 R43 H Me CO ₂ Me A33 R43 H CH ₂ CH = CH ₂ Me A33 R43 H Me Me A34 R43 H Et Me A34 R43 H Me CO ₂ Me A34 R43 H CH ₂ CH = CH ₂ Me A34 R43 H Me Me A35 R43 H Et Me A35 R43 H Me CO ₂ Me A35 R43 H CH ₂ CH = CH ₂ Me A35 R43 H Me Me A36 R43 H Et Me A36 R43 H Me CO ₂ Me A36 R43 H CH ₂ CH = CH ₂ Me A36 R43 H Me Me A37 R43 H Et Me A37 R43 H Me CO ₂ Me A37 R43 H CH ₂ CH = CH ₂ Me A37 R43 H Me Me A38 R43 H Et Me A38 R43 H Me CO ₂ Me A38 R43 H CH ₂ CH = CH ₂ Me A38 R43 H Me Me A39 R43 H Et Me A39 R43 H Me CO ₂ Me A39 R43 H CH ₂ CH = CH ₂ Me A39 R43 H Me Me A40 R43 H Et Me A40 R43 H Me CO ₂ Me A40 R43 H CH ₂ CH = CH ₂ Me A40 R43 H Me Me A41 R43 H Me Et A41 R43 H Me CO ₂ Me A41 R43 H Et Me A41 R43 H CH ₂ CH = CH ₂ Me A41 R43 H COMe Me A41 R43 H COtBu Me A41 R43 H Me Me A42 R43 H Me Et A42 R43 H Me CO ₂ Me A42 R43 H Et Me A42 R43 H CH ₂ CH = CH ₂ Me A42 R43 H COMe Me A42 R43 H COtBu Me A42 R43 H Me Me A43 R43 H Me Et A43 R43 H Me CO ₂ Me A43 R43 H Et Me A43 R43 H CH ₂ CH = CH ₂ Me A43 R43 H COMe Me A43 R43 H COtBu Me A43 R43 H Me Me A44 R43 H Me Et A44 R43 H Me CO ₂ Me A44 R43 H Et Me A44 R43 H CH ₂ CH = CH ₂ Me A44 R43 H COMe Me A44 R43 H COtBu Me A44 R43 HHH A45 R43 H Me H A45 R43 H Me Me A45 R43 Me Me Me A45 R43 Cl Me Me A45 R43 H Me Et A45 R43 H Me nPr A45 R43 H Me cPr A45 R43 H Me CF ₃ A45 R43 H Me Ph A45 R43 H Me CO ₂ Me A45 R43 H Et Me A45 R43 H CH ₂ CH = CH ₂ Me A45 R43 H CH ₂ C≡CH Me A45 R43 H CH ₂ CH ₂ CH ₂ F Me A45 R43 H CH ₂ CH = CCl ₂ Me A45 R43 H cPr Me A45 R43 H CH ₂ Ph Me A45 R43 H Ph Me A45 R43 H SO ₂ CF ₃ Me A45 R43 H COMe Me A45 R43 H COtBu Me A45 R43 H Me Me A46 R43 H Et Me A46 R43 H Me CO ₂ Me A46 R43 H CH ₂ CH = CH ₂ Me A46 R43 H Me Me A47 R43 H Et Me A47 R43 H Me CO ₂ Me A47 R43 H CH ₂ CH = CH ₂ Me A47 R43 HHH A48 R43 H Me H A48 R43 H Me Me A48 R43 Me Me Me A48 R43 Cl Me Me A48 R43 H Me Et A48 R43 H Me nPr A48 R43 H Me cPr A48 R43 H Me CF ₃ A48 R43 H Me Ph A48 R43 H Me CO ₂ Me A48 R43 H Et Me A48 R43 H CH ₂ CH = CH ₂ Me A48 R43 H CH ₂ C ≡CH Me A48 R43 H CH ₂ CH ₂ CH ₂ F Me A48 R43 H CH ₂ CH = CCl ₂ Me A48 R43 H cPr Me A48 R43 H CH ₂ Ph Me A48 R43 H Ph Me A48 R43 H SO ₂ CF ₃ Me A48 R43 H COMe Me A48 R43 H COtBu Me A48 R43 H Me Me A49 R43 H Et Me A49 R43 H Me CO ₂ Me A49 R43 H CH ₂ CH = CH ₂ Me A49 R43 H Me Me A50 R43 H Et Me A50 R43 H Me CO ₂ Me A50 R43 H CH ₂ CH = CH ₂ Me A50 R43 H Me Me A51 R43 H Et Me A51 R43 H Me CO ₂ Me A51 R43 H CH ₂ CH = CH ₂ Me A51 R43 H Me Me A52 R43 H Et Me A52 R43 H Me CO ₂ Me A52 R43 H CH ₂ CH = CH ₂ Me A52 R43 H Me Me A53 R43 H Et Me A53 R43 H Me CO ₂ Me A53 R43 H CH ₂ CH = CH ₂ Me A53 R43 H Me Me A54 R43 H Et Me A54 R43 H Me CO ₂ Me A54 R43 H CH ₂ CH = CH ₂ Me A54 R43 H Me Me A55 R43 H Et Me A55 R43 H Me CO ₂ Me A55 R43 H CH ₂ CH = CH ₂ Me A55 R43 H Me Me A56 R43 H Et Me A56 R43 H Me CO ₂ Me A56 R43 H CH ₂ CH = CH ₂ Me A56 R43 H Me Me A57 R43 H Et Me A57 R43 H Me CO ₂ Me A57 R43 H CH ₂ CH = CH ₂ Me A57 R43 H Me Me A58 R43 H Et Me A58 R43 H Me CO ₂ Me A58 R43 H CH ₂ CH = CH ₂ Me A58 R43 H Me Me A59 R43 H Et Me A59 R43 H Me CO ₂ Me A59 R43 H CH ₂ CH = CH ₂ Me A59 R43 H Me Me A60 R43 H Et M e A60 R43 H Me CO ₂ Me A60 R43 H CH ₂ CH = CH ₂ Me A60 R43 H Me Me A61 R43 H Et Me A61 R43 H Me CO ₂ Me A61 R43 H CH ₂ CH = CH ₂ Me A61 When applying the compound of the present invention, it is usually mixed with an appropriate solid carrier or liquid carrier. And, if desired, a surfactant, a penetrant, a spreading agent, a thickener, an antifreezing agent, a binder, an anti-caking agent, a disintegrating agent and an anti-decomposition agent. Emulsifiable concen
trate), wettable powder, water solvent
soluble powder), water dispersible gr
anule), water soluble granule, suspension concentrate, emulsion (emaulsion, o)
il in water, suspoemulsio
n), microemulsion, microemulsion, dustable powder, granule, and gel can be practically used in the preparation of any dosage form. In addition, from the viewpoint of labor saving and improvement of safety, the preparation of any of the above dosage forms can be provided by being enclosed in a water-soluble package.

Examples of solid carriers 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 styrylphenyl 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 usually preferably in the range of 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, synergist, fertilizer, soil conditioner and the like.

In particular, by applying a 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 medicine, and a higher pest control effect can be expected. On this occasion,
A combination with a plurality of known pesticides is also possible at the same time. Examples of the kind of agrochemical used in combination with the compound of the present invention include, for example, Farm Chemicals Handbook (Farm
Chemicals Handbook) 1999 edition. Specific examples of the common names are as follows, but are not necessarily limited thereto.

Fungicide: acibenzolar-S-methyl (ac
ibenzolar-S-methyl), acylaminobenzamide (acyla
minobenzamide), ambam, ampropyfos, anilazine, azaconazole, azoxystrobin (azoxyst)
robin), benalaxyl, benodanil (be
nodanil), benomyl (benomil), benzazole (ben)
thiazole), benzamacril, binapacryl, biphenyl, bitertanol, bethoxazin
e), bordeaux mixture, blasticidin-S, bromoconazole
onazole), bupirimate, butiobate, calcium polysulfide (calciu)
m polysulfide), captafol, captan, copper oxychloride (copper
oxychloride), carpropamid, carbendazim, carboxi
n), CGA-279202 (test name), quinomethionate (c
hinomethionat), clobenthiazon (chlobenthiazon)
e), chlorfenazol, chloroneb, chlorothaloni
l), chlozolinate, kufuraneb (c
ufraneb), cymoxanil, cyproconazol, cyprodinil,
Cyprofuram, dazomet,
Debacarb, dichlorophen
en), diclobutrazol, diclhlofluanid, diclomedin (diclomed)
ine), dichloran, dithofencarb, diclosymet,
Difenoconazole, diflumetorim, dimethirimol
l), dimethomorph, diniconazole, diniconazole-M
M), dinocap, diphenylamine (diph)
enylamine), dipyrithione, ditarimphos, dithianon, dodemorph, dodine, drazoxolon, edifenpho
s), epoxyconazole (epoxiconazole), etaconazole (etaconazole), etirimol (ethirimol), etridianol (etridiazole), famoxazone (fam)
oxadone), fenarimol, febuconazole, fenamidone,
Fendazosulam, fendazosulam
uram), fenhexamid, fenpiclonil, fenpropidin (fenpropid)
in), fenpropimorph (fenpropimorph), fentin (fentin), ferban (ferbam), ferimzone (ferimzone), fluazinam (fluazinam), fludioxonil (fludioxonil), fluoroimide (fluoroimi)
de), fluquinconazole, flusilazole, flusulfamide
lfamide, flutlanil, flutriafol, folpet, fosetyl-aluminium, fuberidazole, furalaxy
l), furametpyr, guazatine
ne), hexachlorobenzene,
Hexaconazole (hexaconazole), hymexazol (hymexazol), imazalil (imazalil), imibenconazole (imibenconazole), iminoctazine (iminoc)
tadine), ipconazole, iprobenfos, iprobedione, iprodione, isoprothiolane, iprovalicarb, iprovalicarb, kasugamycin,
Kresoxim-methyl, mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metconazole, methasolul (methasul)
focarb), metiram (metiram), metominostrobin (metominostrobin), microbutanil (myclobutani)
l), MTF-753 (test name), nabam, nickel bis (dimethyldithiocarbamate) (nickel bis
(dimethyldithiocarbamate)), nitrothal-isopropyl, nuarimo
l), NNF-9425 (test name), octillinone (octhili
none), offurace, oxadixyl (oxa)
dixyl), oxycarboxin, oxpoconazole fumarate,
Pefurzoate, penconazole (penc)
onazole), pencuron (pencycuron), phthalide (phthalide), piperalin (piperalin), polyoxins (polyoxins), potassium bicarbonate (potassiumhydroge)
n carbonate), probenazole, prochloraz, procymidon
e), propamocarbhydrochlorid
e), propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil
l), pyroquilon, quinomethionate
(quinomethionate), quinoxyfen,
Quintozene, RH7281 (test name), sodium hydrogen carbonate (sodium hydrogen carbonate), sodium hypochlorite (sodium hypochlorite), sulfur (sulfu
r), spiroxamine (spiroxamine), tebuconazole (tebuconazole), technazen (tecnazene), tetraconazole (tetraconazole), thiabendazole (thi
abendazole), thiadiazin / milneb, thifluzamide, thiophanate-methyl, thioram, thiram, tolclofos-methyl, tolylfluanid, triadimefon,
Triadimenol (toriadimenol), triazoxide (triazoxide), tricyclazole (tricyclazole),
Tridemorph, triflumizole (trif)
lumizole), triforine, triticonazole, validamyci
n), vinclozolin, zinc sulfate (zinc
sulfate), zineb, ziram and shiitake mushroom mycelium extract.

Bactericide: Streptomycin (st
reptomycin), tecloftalam, oxyterracycline, oxolinic acid, and the like.

Nematicide: aldoxycarb
b), cadusafos, fostiasate (fo
sthiazate), fosthietan, oxamyl and fenamiphos.

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

Insecticides: Abamectin, acephate, acetamipir
id), aldicarb, allesulin (alle)
thrin), azinphos-methyl, bendiocarb, benfuracarb
acarb), bensultap, bifenthrin, buprofezin, butocarboxin, carbaryl
yl), carbofuran, carbosulfan, cartap, chlorfenapyr, chlorpyrif
os), chlorfenvinphos, chlorfluazuron, chlorthianidin, chromafenozid
e), chlorpyrifos-methyl,
Cycloprothrin, cyfluthrin (c
yfluthrin), beta-cyfluthri
n), cypermethrin (cypermethrin), cyromazine (c
yromazine), cyhalothrin, lambda
Cyhalothrin (lambda-cyhalothrin), deltamethrin (deltamethrin), diafenthiuron (diafenthiuro)
n), diazinon, diacloden (diacl)
oden), diflubenzuron, dimethylvinphos, diphenolane (dio)
fenolan), disulfoton, dimethoate, emamectin benzoate (emam)
ectin-benzoate), EPN, esfenvalerate (esfen)
valerate), ethiofencarb, ethiprole, etofenprox (eto)
fenprox), etrimfos, fenitrothion, fenobucar
b), fenoxycarb, fenpropathrin, fenvalerate
rate), fipronil, fluacrypyrim, flucythrinat
e), flufenoxuron, flufenprox, flufenprox, tau-fluvalinate, fonophos, formetanate, formothion
ion), furathiocarb, halofenozide, hexaflumuron
on), hydramethylnon, imidacloprid, isofenph
os), indoxacarb, indoxacarb, isoprocarb, isoxathion, lufenuron, malathion
n), metal aldehyde (metaldehyde), methamidophos (me
thamidophos), methidathion, methacrifos, metalcarb
b), methomil (methomyl), mesoprene (methopren)
e), methoxychlor, methoxyfenozide, monoctophos (monoc)
rotophos), muscalure, nidinotefuran, nitenpyra
m), omethoate, oxydemeton-methyl, oxamyl,
Parathion, parathion-methyl (parat
hion-methyl), permethrin, phenthoate, phoxim, phorate, phosalone, phosmet, phosphamidon, pirimicarb, pirimiphos-methyl (pirimi)
phos-methyl), profenofos, protrifenbute, pymetrozine (pym
etrozine), pyraclofos, pyriproxyfen, rotenone, sulprofos, silafluofen
ofen), spinosad, sulfotep (sulf)
otep), tebufenozide, teflubenzuron, tefluthrin
n), terbufos, tetrachlorovinphos, thiacloprid
d), thiocyclam, thiodicarb (thi
odicarb), thiamethoxam, thiofanox, thiometon,
Tolfenpyrad, tolofenpyrad (t
ralomethrin), trichlorfon, triazuron, triflumuro
n) and vamidothion 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 hectare (ha) as an active ingredient.
About 5 to 50 kg is appropriate.

Formulation examples of the formulations using the compound of the present invention are shown below. However, the composition examples of the present invention are not limited to these. In the following formulation examples, "parts" means parts by weight.

[Wettable powder] Compound of the present invention 0.1 to 80 parts Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts Others, for example, anti-caking agent, anti-decomposition agent, etc. I can give you.

[Emulsion] Compound of the present invention 0.1 to 30 parts Liquid carrier 45 to 95 parts Surfactant 4.9 to 15 parts Others 0 to 10 parts Others include, for example, spreading agents, decomposition inhibitors and the like. Can be

[Suspension] Compound of the present invention 0.1 to 70 parts Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts Others, for example, antifreezing agents, thickeners And the like.

[Water dispersible granules] 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. No.

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

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

[Powder] Compound of the present invention 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0 to 5 parts Others include, for example, a drift inhibitor and a decomposition inhibitor.

Next, specific examples of the formulation of the pesticidal composition containing the compound of the present invention as an active ingredient will be shown more specifically, but the present invention is not limited thereto.

In the following formulation examples, “parts” means parts by weight.

[Formulation Example 1] Water-dispersible compound of the present compound No. 1 1 25 parts Pyrophyllite 71 parts Solpol 5039 2 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) Carplex # 80D 2 parts (synthetic hydrous silicic acid: Shiono The above is uniformly mixed and pulverized into a wettable powder.

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

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

[Compounding Example 4] Water dispersible granule (dry flowable agent) 1 75 parts Hytenol NE-15 5 parts (Anionic surfactant: Daiichi Kogyo Seiyaku Co., Ltd.) Vanirex N 10 parts (Anionic surfactant: Nippon Paper Industries Co., Ltd.) Carplex # 80D 10 parts (Synthetic hydrous silicic acid: trade name of Shionogi & 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. We assume granule 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.

When used, the above-mentioned wettable powder, emulsion, flowable and granular wettable powder are diluted 50 to 20,000 times with water so that the active ingredient is 0.005 to 0.005 per hectare (ha).
Spray to 50kg.

[0215]

[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] 2- (1- (5- (1,3,4-trimethylpyrazol-5-yl) isoxazol-4-yl)
Synthesis of pyrazol-3-yl) -1,3-thiazole (Compound No. 1)

[0216]

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In a solution of 3.0 g of 2-pyrazol-3-yl-1,3-thiazole in 30 ml of acetonitrile, 8.2 g of potassium carbonate was added. After adding 6.1 g of methyl bromoacetate, the temperature was increased, and the mixture was stirred for 2 hours under reflux with heating. After evaporating the solvent under reduced pressure, the residue was dissolved in ethyl acetate, washed with water and washed with brine, 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 purified by silica gel column chromatography (hexane: ethyl acetate = 1: 2) to obtain 3.7 g of compound (a).

In a solution of 3.6 g of compound (a) and 2.8 g of 1,3,4-trimethylpyrazole-5-carbonyl chloride in 40 ml of tetrahydrofuran, 4.5 g of potassium t-butoxide was added under ice-cooling. After stirring at room temperature overnight, the reaction solution was poured into dilute aqueous hydrochloric acid and extracted with ethyl acetate. The organic layer is dried over anhydrous sodium sulfate,
The solvent was distilled off under reduced pressure to obtain 5.2 g of compound (b).

In a mixed solvent of an 18% aqueous hydrochloric acid solution and 1,4-dioxane, 5.2 g of the compound (b) was added, and the mixture was stirred under reflux with heating for 7 hours. After 1,4-dioxane was distilled off under reduced pressure, the mixture was neutralized with an aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. After washing with water and a saturated saline solution, 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 to obtain 1.75 g of compound (c).

Compound (c) (1.0 g) was mixed with acetonitrile 1
N, N-dimethylformamide dimethyl acetal (0.47 g) was added to the solution dissolved in 5 ml, and the mixture was stirred at 80 ° C for 3 hours. The solvent was distilled off under reduced pressure to obtain a crude product. This was washed with isopropyl ether to obtain 1.13 g of compound (d).

Compound (d) (0.45 g) was added to ethanol 15
0.11 hydroxylamine hydrochloride dissolved in 0.1 ml
g and a catalytic amount of p-toluenesulfonic acid were added, and the mixture was stirred overnight under reflux with heating. After evaporating the solvent under reduced pressure, the residue was dissolved in ethyl acetate, washed with water and washed with brine, 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 purified by preparative TLC (hexane: ethyl acetate = 1: 2). 0.14 g of 1
Obtained.

¹ H-NMR (CDCl ₃ , δ ppm): 1.81 (3H, s), 2.24 (3
H, s), 3.73 (3H, s), 6.98 (1H, d), 7.38 (1H, d), 7.42 (1H, d),
7.89 (1H, d), 8.91 (1H, s) [Synthesis Example 2] 1-aza-2- (2- (5- (3,5-dichloro-1-methylpyrazol-4-yl) isoxazole-4- Yl) (1,3-thiazol-4-yl))
Synthesis of -1-methoxyprop-1-ene (Compound No.
2)

[0223]

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Tetrahydrofuran 10 cooled to -5 ° C
19 ml of n-butyllithium was added to 0 ml. 1.8 g of N- (trimethylsilyl) acetamide in the solution
Was added and stirred for 0.5 hour. Methyl-3,5-dichloro-1-methylpyrazole-4-carboxylate 1.5
g in 10 ml of tetrahydrofuran was added dropwise to the reaction solution while maintaining the temperature at 0 ° C. or lower. 0 ° C
After stirring for 2 hours, the mixture was adjusted to pH 4 by adding acetic acid, diluted with water, and the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, washed with water and washed with saturated saline, and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain a crude product. This was purified by silica gel column chromatography (ethyl acetate) to obtain 0.91 g of compound (e).

In a solution of 0.8 g of the compound (e) in 10 ml of 1,4-dioxane, 1.37 g of Lawesson's reagent was added, and the mixture was stirred at room temperature overnight. After removing the solid by filtration, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 1: 1) to obtain 0.8 g of compound (f).

Compound (f) (0.8 g) was treated with methanol (15 m).
To the solution, 0.62 g of 4-aza-1-bromo-4-methoxy-3-methylbut-3-en-2-one was added, and the mixture was heated under reflux for 1 hour. The solvent was distilled off under reduced pressure, neutralized with a solution of 0.5 g of potassium carbonate dissolved in 20 ml of water, and extracted with ethyl acetate. After washing with water and a saturated saline solution, the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1) to obtain 0.84 g of compound (g).

To a solution of the compound (g) (0.45 g) in acetonitrile (10 ml) was added N, N-dimethylformamide dimethyl acetal (0.59 g), and the mixture was stirred at 80 ° C. for 6 hours. After evaporating the solvent under reduced pressure, the residue was dissolved in ethyl acetate, washed with water and washed with saturated saline, the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product. Obtained. This was washed with isopropyl ether to obtain 0.42 g of compound (h).

Compound (h) (0.42 g) was added to ethanol 10
72.6 ml of hydroxylamine hydrochloride dissolved in
The resulting mixture was stirred for 3 hours while heating under reflux. After evaporating the solvent under reduced pressure, the residue was dissolved in ethyl acetate, washed with water and washed with saturated saline, and the organic layer was dried over anhydrous sodium sulfate.
The solvent was distilled off under reduced pressure to obtain a crude product. This is preparative T
LC (hexane: ethyl acetate = 2: 1). 80 mg were obtained. The oxime moiety is represented by Z
Or E-form of a single compound.

¹ H-NMR (CDCl ₃ , δ ppm): 2.30 (3H, s), 3.93 (3
H, s), 4.01 (3H, s), 7.57 (1H, s), 8.87 (1H, s). 3 was synthesized. The configuration of the oxime moiety was a single compound in the Z or E form.

[0230]

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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 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 1/20000 are pot in a sufficient amount. After air-drying, the cylinder was set up, and the second instar larva of the brown planthopper, 1 pot per pot
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.

[0234]

## EQU1 ## As a result, the following compounds showed a mortality rate of 80% or more.

The compound of the present invention no. : 1.

[Test Example 2] Insecticidal test against black leafhopper Rice foliage was immersed for about 10 seconds in an emulsion of the compound of the present invention at a concentration of 500 ppm. 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.

[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 adult wingless 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, the mortality of adults and larvae was determined by the following formula. The test was performed in two sections.

Mortality (%) = [Number of dead insects / (Number of dead insects + Number of surviving insects)] × 100 As a result, the following compounds showed a mortality of 80% or more.

The compound of the present invention no. : 1, 3.

Test Example 4 Contact Insecticidal Test against Japanese moth Perilla leaves were 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.

Compound No. of the present invention : 1.

[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, in which the second instar larvae of cucumber beetle were placed in a petri dish at a concentration of 1 per 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 two sections.

As a result, the following compounds showed a mortality of 80% or more.

The compound of the present invention No. : 1.

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 depending on the compound depending on the compound) is diluted with water containing a spreading agent to prepare a drug solution having a concentration of 500 ppm, and the drug 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 elapse 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, 3.

[0248]

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 disturbing ecosystems due to persistence. Accordingly, the present invention provides a novel insecticide or fungicide having low toxicity and low residual, and also provides an underwater biofouling inhibitor having little effect on ecosystems and secondary pollution.

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Toshiro Miyake 1470, Shirooka, Shirooka-cho, Minami-Saitama-gun, Saitama Nissan Chemical Industry Co., Ltd. Inside the Biological Sciences Laboratory, Chemical Industry Co., Ltd. DD62 EE03 4H011 AC01 AC04 BA01 BB10 BC01 BC07 BC09 BC17 BC18 BC19 BC20 DA02 DA13 DA15 DC04 DC05 DC06 DC08 DH02 DH03 DH10 DH14

Claims (4)

[Claims] (1) Formula (1):[Wherein Q is R and (R¹)_nThiazoly substituted with
Or R and (R¹)_nPyrazolyl substituted with
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. R is a heterocyclic group optionally substituted with G (provided that
Heterocyclic groups are furyl, pyrrolyl, oxazolyl, isoxa
Zolyl, thiazolyl, isothiazolyl, pyrazolyl, i
Midazolyl, 1,3,4-oxadiazolyl, 1,2,2
4-oxadiazolyl, 1,3,4-thiadiazolyl,
1,2,4-thiadiazolyl, 1,2,4-triazolyl
1,2,3-thiadiazolyl, 1,2,3-tria
Zolyl, 1,2,3,4-tetrazolyl, pyrimidini
, Pyrazinyl, pyridazinyl, 1,3,5-triazi
Nil, 1,2,4-triazinyl, benzothiazolyl,
Benzimidazolyl, indazolyl, benzoxazoly
Quinolinyl, isoquinolinyl, quinoxalinyl,
Tarazinyl, cinnolinyl or quinazolinyl
You. ) OrAnd R¹Is halogen, C₁~ C_TenAlkyl, C₁~ C_FiveArco
Xycarbonyl, NO _Two, CN, -NU¹U^TwoOr -N
= CT⁷T⁸And R^TwoIs H, C₁~ C_TenAlkyl, C_Two~ C₆Alkenyl,
C_Two~ C₆Alkynyl, C₁~ C₆Haloalkyl, C_Two~ C₆
Haloalkenyl, C_Two~ C₆Haloalkynyl, C _Three~ C₆C
Rocycloalkyl, C₁~ C_ThreeSubstituted with alkyl
Good C_Three~ C₆Cycloalkyl, C_Two~ C_FourAlkoxya
Lequil, CH_ThreeSCH_Two, CH_ThreeOC_TwoH_FourOCH_Two, R^aso
Replaced C₁~ C_FourAlkyl, R^bC substituted with₁~ C
_FourAlkyl, R^aC substituted with_Two~ C_FourAlkenyl, tet
Lahydropyranyl, (CH_Three)_ThreeSi, C₁~ C_FourAlkyl
Sulfonyl, halogen or C₁~ C_FourSubstitute with alkyl
Phenylsulfonyl, -SO_TwoCF_Three,
C₁~ C_FourMonoalkylaminosulfonyl, C_Two~ C₈Zia
Alkylaminosulfonyl, phenylaminosulfonyl,
Pyrazolyl optionally substituted with Z, substituted with Z
Optionally imidazolyl, Z optionally substituted with Z
Azolyl, phenyl optionally substituted with Z,
Optionally substituted pyridyl, optionally substituted with Z
Pyrimidinyl, pyrazini optionally substituted with Z
Le, C_Two~ C_FiveCyanoalkyl, C_Three~ C₉Alkoxycal
Bonylalkyl, -C (= O) T¹, -C (= S) T¹,
-P (= O) T^TwoT^Three, -P (= S) T^TwoT^Three, Alkali gold
Genus atom, alkaline earth metal atom or NHT^FourT^FiveT⁶so
Yes, R^ThreeIs H, halogen, C₁~ C_TenAlkyl, C_Two~ C₆A
Lucenyl, C_Two~ C₆Alkynyl, C₁~ C₆Haloalk
Le, C_Two~ C₆Haloalkenyl, C_Two~ C₆Halo alkini
Le, C_Three~ C₆Halocycloalkyl, C₁~ C_ThreeWith alkyl
Optionally substituted C_Three~ C₆Cycloalkyl, C₁~
C₆Alkoxy, C_Two~ C₆Alkenyloxy, C_Two~ C₆
Alkynyloxy, C₁~ C₆Haloalkoxy, C_Two~ C₆
Haloalkenyloxy, C_Two~ C₆Haloalkynyloxy
Si, C_Two~ C_FourAlkoxyalkyl, R^aC substituted with₁
~ C_FourAlkyl, R^bC substituted with₁~ C_FourAlkyl, R
^aC substituted with_Two~ C_FourAlkenyl, (CH_Three)_ThreeSi,
C₁~ C_FourAlkylsulfenyl, C ₁~ C_FourAlkylsul
Finil, C₁~ C_FourAlkylsulfonyl, halogen if
Kuha C₁~ C_FourPhenyl optionally substituted with alkyl
Sulfonyl, -SO_TwoCF_Three, C_Two~ C_FiveCyanoalkyl,
C_Three~ C₉Alkoxycarbonylalkyl, CN, -NU
¹U^Two, Phenoxy, phenylamino, -C (= O)
T¹, -C (= S) T¹, Morpholinyl, piperidyl, Z
Optionally substituted with pyrazolyl, substituted with Z
Optionally imidazolyl, thia optionally substituted by Z
Zolyl, phenyl optionally substituted with Z, substituted with Z
Pyridyl, which may be substituted by Z
Pyrazinyl or pyrazini optionally substituted by Z
N 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
It may form a ring. 1) arbitrarily selected from
From 4 to 4 substituents or at adjacent substitution positions
5- to 8-membered ring formed by alkylene
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 by one or more kinds,^bIs halogen and C₁~ C_FourSelected from alkyl
Benzoyl optionally substituted with one or more kinds,^cIs halogen and C₁~ C_FourSelected from alkoxy
A phenyl optionally substituted with at least one kind of^dRepresents C which may be substituted with halogen_Two~ C_FourAl
Kenyl. ] The isoxazole derivative represented by these. 2. The isoxazole derivative according to claim 1, wherein Q is thiazolyl substituted with R. 3. The isoxazole derivative according to claim 1, wherein Q is pyrazolyl substituted with R. 4. An agricultural chemical comprising at least one of the isoxazole derivatives according to claim 1 as an active ingredient.